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

Abstract

A compound represented by the following general formula is used for an organic light-emitting element. X1 to X3 each represent N or C (R). R represents H, D, or a substituent group. X4 represents N or C (R1). X5 represents N or C (R2). X6 represents N or C (R3). Only one from among X4 to X6 is N. R1 to R5 are each H, D, a cyano group, an alkyl group, an aryl group, or a donor group, at least one of these being a cyano group and at least one being a donor group. Ar1 and / or Ar2 is a heteroaryl group bound by N. L1 represents a single bond or a linking group.

Description

Compound, light-emitting material and light-emitting device

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

[0002] Research into improving the luminous efficiency of light-emitting elements such as organic electroluminescence elements (organic EL elements) 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 elements. Among these efforts, research into organic electroluminescence elements that utilize delayed fluorescent materials has also been seen.

[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. These include many compounds in which a donor group and an acceptor group are substituted on an aromatic ring. For example, a compound having the following skeleton in which a pyridine ring is substituted with a carbazol-9-yl group as a donor group and a substituted triazinyl group as an acceptor group has been proposed (see Patent Document 1).

[0005]

[0006] WO2021 / 157600

[0007] Even among materials that emit delayed fluorescence, none have been provided to date that have extremely good properties and no practical issues. For example, Patent Document 1 describes that the above-mentioned delayed fluorescence materials have a short delayed fluorescence lifetime and excellent luminescence properties, but it would be desirable to provide delayed fluorescence materials with even shorter delayed fluorescence lifetimes. Since a long delayed fluorescence lifetime leads to device degradation and a decrease in luminous efficiency at high brightness, in order to realize a long-life organic electroluminescence device, it is necessary to develop delayed fluorescence materials with even shorter delayed fluorescence lifetimes. However, improvements to delayed fluorescence materials are still in the trial and error stage, and it is not easy to generalize the chemical structure of useful luminescent materials.

[0008] Under these circumstances, the present inventors have conducted extensive research with the aim of providing compounds that are more useful as delayed fluorescent materials for light-emitting devices, and have conducted extensive research with the aim of deriving and generalizing a general formula for compounds that are more useful as delayed fluorescent materials.

[0009] As a result of intensive research to achieve the above object, the present inventors have found that compounds having a structure satisfying specific conditions are useful as light-emitting materials. 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): [In the general formula (1), X １ ~X ３ Each independently represents N or C(R), but X １ ~X ３ At least one of Ar is N. R represents a hydrogen atom, a deuterium atom, or a substituent. １ and Ar ２ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom, １ and Ar ２ At least one of L is a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom. １ represents a single bond or a divalent linking group. ４ is N or C(R １ ) and X５ is N or C(R ２ ) and X ６ is N or C(R ３ ), but X ４ ~X ６ Only one of the R is N. １ ~R ５ each independently represents a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a donor group. １ ~R ５ At least one of R １ ~R ５ 0 to 2 of R are hydrogen atoms or deuterium atoms, １ ~R ５ and 0 to 1 of X are substituted or unsubstituted aryl groups.] [2] X ５ The compound according to [1], wherein X is N. [3] ６ The compound according to [1], wherein R is N. [4] １ ~R ５ [5] The compound according to any one of [1] to [3], wherein only one of R is a substituted or unsubstituted aryl group. ４ [6] The compound according to [4], wherein R is a substituted or unsubstituted aryl group. １ ~R ５ [7] The compound according to any one of [1] to [5], wherein one of R １ ~R ５ [8] The compound according to any one of [1] to [5], wherein two of R １ ~R ５ [9] The compound according to any one of [1] to [8], wherein three of R are donor groups.

[10] The compound according to any one of [1] to [8], wherein the donor groups are substituted or unsubstituted carbazol-9-yl groups.

[11] The compound according to any one of [1] to [8], wherein R ３ ~R ５

[11] The compound according to any one of [4] to [9], wherein R is each independently a substituted or unsubstituted aryl group or a donor group. ２ , R ４and R ５

[12] The compound according to any one of [3] to [9], wherein each of X is independently a substituted or unsubstituted aryl group or a donor group. １ ~X ３

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

[11] , wherein Ar is N. １ is a substituted or unsubstituted carbazol-9-yl group, and Ar ２

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

[12] , wherein Ar is a substituted or unsubstituted aryl group. １ and Ar ２

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

[12] , wherein each of L is independently a substituted or unsubstituted carbazol-9-yl group. １

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

[14] , wherein R is a single bond. １is a hydrogen atom.

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

[16] , which has at least one deuterium atom.

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

[17] .

[19] A delayed fluorescent material comprising the compound according to any one of [1] to

[17] .

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

[17] .

[21] An organic semiconductor device comprising the compound according to any one of [1] to

[17] .

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

[17] .

[23] The organic light-emitting device according to

[22] , which has a layer comprising the compound, the layer also comprising a host material.

[24] The organic light-emitting device according to

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

[25] The organic light-emitting device according to

[23] or

[24] , which has a layer containing the compound, and the layer also contains a light-emitting material having a structure different from that of the compound.

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

[23] to

[25] , wherein the compound has the largest amount of light emission among the materials contained in the organic light-emitting device.

[27] The organic light-emitting device according to

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

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

[22] to

[27] , which is an organic electroluminescence device.

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

[22] to

[28] , which emits delayed fluorescence.

[0010] The compound of the present invention exhibits excellent light-emitting properties and is useful as a material for an organic light-emitting device.

[0011] 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 ( ２ In 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.

[0012] [Compound Represented by General Formula (1)] The compound represented by the following general formula (1) will be explained.

[0013] In general formula (1), X １ ~X ３ Each independently represents N or C(R). １ ~X ３ At least one of the groups is N. R represents a hydrogen atom, a deuterium atom, or a substituent. The substituent may be selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In a preferred embodiment of the present invention, X １ ~X ３ is N. In one aspect of the present invention, X １ and X ３ is N and X ２ is C(R). In one aspect of the present invention, X １ and X ２ is N and X ３ is C(R). In one aspect of the present invention, X１ is N and X ２ and X ３ is C(R). In one aspect of the present invention, X ２ is N and X １ and X ３ is C(R). In one embodiment of the present invention, R is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, R is an alkyl group optionally substituted with a deuterium atom. In one embodiment of the present invention, R is a deuterium atom, an alkyl group, or an aryl group optionally substituted with an aryl group.

[0014] In general formula (1), X ４ is N or C(R １ ) and X ５ is N or C(R ２ ) and X ６ is N or C(R ３ ), but X ４ ~X ６ In a preferred embodiment of the present invention, only one of X ５ is N and X ４ is C(R １ ) and X ６ is C(R ３ In another preferred embodiment of the present invention, X ６ is N and X ４ is C(R １ ) and X ５ is C(R ２ In one aspect of the present invention, X ４ is N and X ５ is C(R ２ ) and X ６ is C(R ３ )

[0015] In general formula (1), R １ ~R ５ each independently represents a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a donor group. １ and Ar ２ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom.

[0016] R １ ~R ５ The alkyl group may be linear, branched, or cyclic. Two or more of the linear, cyclic, and branched groups may be mixed. The number of carbon atoms in the alkyl group may be, for example, 1 or more, 2 or more, or 4 or more. The number of carbon atoms may be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, an isohexyl group, a 2-ethylhexyl group, an n-heptyl group, an isoheptyl group, an n-octyl group, an isooctyl group, an n-nonyl group, an isononyl group, an n-decanyl group, an isodecanyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The alkyl group as a substituent may be further substituted with, for example, a deuterium atom, an aryl group, an alkoxy group, an aryloxy group, or a halogen atom. In one embodiment of the present invention, the substituent of the alkyl group is one or more selected from the group consisting of an aryl group and a deuterium atom. In a preferred embodiment of the present invention, the alkyl group is unsubstituted and can be selected from the group consisting of, for example, a methyl group, an ethyl group, an isopropyl group, and a tert-butyl group.

[0017] R １ ~R ５ , Ar １ and Ar ２The aryl group may be a monocyclic 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 triphenylene ring. In one embodiment of the present invention, the aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthalen-1-yl group, or a substituted or unsubstituted naphthalen-2-yl group, preferably a substituted or unsubstituted phenyl group. The substituent of the aryl group may be selected, for example, from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In one embodiment of the present invention, the substituent of the aryl group is one or more selected from the group consisting of an alkyl group, an aryl group, and a deuterium atom. In a preferred embodiment of the present invention, the aryl group is substituted with at least one deuterium atom. In one embodiment of the present invention, the aryl group is unsubstituted. １ ~R ５ , Ar １ and Ar ２ Specific examples of substituted or unsubstituted 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.

[0018] In addition to the above specific examples, groups in which all hydrogen atoms present in Ar1 to Ar20 are substituted with deuterium atoms are exemplified here as Ar40 to Ar59 in this order. １ ~R ５ The aryl group that R can take is Ar1 or Ar40. １ ~R ５The aryl groups that R can take are selected from the group consisting of Ar2 to Ar11, Ar21 to Ar30, and Ar41 to Ar50. １ ~R ５ The aryl groups that R can take are selected from the group consisting of Ar12 to Ar16, Ar31 to Ar35, and Ar51 to Ar55. １ ~R ５ The aryl group represented by R is selected from the group consisting of Ar1, Ar12 to Ar16, Ar40, Ar31 to Ar35, and Ar51 to Ar55. １ ~R ５ The aryl group represented by Ar is selected from the group consisting of Ar21 to Ar59. １ and Ar ２ The aryl group that can be taken by Ar is Ar or Ar. １ and Ar ２ The aryl group that can be taken by Ar is selected from the group consisting of Ar2 to Ar11, Ar21 to Ar30, and Ar41 to Ar50. １ and Ar ２ The aryl group that can be taken by Ar is selected from the group consisting of Ar12 to Ar16, Ar31 to Ar35, and Ar51 to Ar55. １ and Ar ２ The aryl group that can be taken by Ar is selected from the group consisting of Ar1, Ar12 to Ar16, Ar40, Ar31 to Ar35, and Ar51 to Ar55. １ and Ar ２ The aryl group which can be taken by is selected from the group consisting of Ar21 to Ar59.

[0019] R in general formula (1) １ ~R ５ At least one of R is a donor group. １ ~R ５The donor groups that can be used do not include substituted or unsubstituted aryl groups. The "donor group" can be selected from groups with a negative Hammett σp value. The 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).

[0020] R １ ~R ５ The donor group 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.

[0021] The donor group in the present invention is preferably a group containing a substituted amino group. It may be a substituted amino group or an aryl group to which a substituted amino group is bonded, particularly a phenyl group to which a substituted amino group is bonded. In a preferred embodiment of the present invention, the donor group is a substituted amino group. The substituent bonded to the nitrogen atom of the substituted amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. The substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group. Here, the two aryl groups constituting the diarylamino group may be bonded to each other, or the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.

[0022] R １ ~R ５ The donor group which can be taken as the donor group is preferably a group represented by the following general formula (a).

[0023] 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 １７ may be bonded to each other to form a cyclic structure.

[0024] Z １ ~Z ４In one embodiment of the present invention, the number of N's is preferably 0 to 3, more preferably 0 to 2. １ ~Z ４ In one aspect of the present invention, the number of N is 1. １ ~Z ４ The number of N is 0. １４ ~R １７ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. The substituent may be selected from, for example, Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. １４ ~R １７ When two or more of R represent substituents, the two or more substituents may be the same or different. １４ ~R １７ It is preferred that 0 to 2 of these be substituents. For example, one may be a substituent, or none may be a substituent (R １４ ~R １７ may be a hydrogen atom or a deuterium atom). １４ and R １５ , R １５ and R １６ , R １６ and R １７may be bonded to each other to form a cyclic structure. The cyclic structure may be any of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring, or may be a condensed ring of these. An aromatic ring or a heteroaromatic ring is preferred. An example of the aromatic ring is a substituted or unsubstituted benzene ring. The benzene ring may be condensed with another benzene ring or a heterocyclic ring such as a pyridine ring. The heteroaromatic ring refers to a ring exhibiting aromaticity containing a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring; for example, a 5-membered ring or a 6-membered ring can be employed. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be employed as the heteroaromatic ring. In a preferred embodiment of the present invention, the cyclic structure is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, or a pyrrole ring of a substituted or unsubstituted indole. The benzofuran, benzothiophene, and indole referred to here may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. A substituted or unsubstituted aryl group is preferably bonded to the nitrogen atom constituting the pyrrole ring of indole, and examples of the substituent include a substituent selected from any of Substituent Groups A to E. The cyclic structure may be a substituted or unsubstituted cyclopentadiene ring. In one aspect of the present invention, R １４ and R １５ , R １５ and R １６ , R １６ and R １７ In one embodiment of the present invention, a pair of R １４ and R １５ , R １５ and R １６ , R １６ and R １７ are not bonded to each other to form a ring structure.

[0025] In the general formula (a), Z ５ represents C or N, Ar ５ represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. ５ is C, and Ar ５ is a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. ５ is N, and Ar ５ is a substituted or unsubstituted heteroaromatic ring. ５ An example of the aromatic ring that can be used by Ar is a benzene ring. The benzene ring may be further condensed with another benzene ring, or may be condensed with a heterocyclic ring such as a pyridine ring. ５ The heteroaromatic ring that can be adopted by Z is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring can be adopted. In one embodiment of the present invention, a furan ring, a thiophene ring, a pyrrole ring, an imidazole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring can be adopted as the heteroaromatic ring. In one embodiment of the present invention, Z ５ is C, and the heteroaromatic ring is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, a pyridine ring of a substituted or unsubstituted quinoline, or a pyridine ring of a substituted or unsubstituted isoquinoline. ５ is N, and the heteroaromatic ring is a pyrrole ring of substituted or unsubstituted indole, or an imidazole ring of substituted or unsubstituted benzimidazole. The benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole referred to here may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A, may be substituted with a substituent selected from Substituent Group B, may be substituted with a substituent selected from Substituent Group C, may be substituted with a substituent selected from Substituent Group D, or may be substituted with a substituent selected from Substituent Group E.

[0026] Z in general formula (a) ５ When is C, it is preferably a group represented by the following general formula (b):

[0027] In the general formula (b), Z １ is C-R １４ or N, Z ２ is C-R １５ or N, Z ３ is C-R １６ or N, Z ４ is C-R １７ or N, Z ６ is C-R １８ or N, Z ７ is C-R １９ or N, Z ８ is C-R ２０ or N, Z ９ is C-R ２１ or N. １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ may be bonded to each other to form a cyclic structure. １ ~Z ４ , R １４ ~R １７ For Z in general formula (b), the corresponding explanation for general formula (a) can be referred to. ６ ~Z ９ , R １８ ~R ２１ is Z in general formula (a). １ ~Z ４ , R １４ ~R １７ These correspond in order to Z in general formula (a). １ ~Z ４ , R １４ ~R １７ In one aspect of the present invention, Z １ ~Z ４ , Z ６ ~Z ９In one embodiment of the present invention, the number of N's is preferably 0 to 2, and more preferably 0 or 1. １ ~Z ４ , Z ６ ~Z ９ In a preferred embodiment of the present invention, the number of N groups is 1. １ ~Z ４ , Z ６ ~Z ９ The number of N groups is 0. When it is 0, it represents a substituted or unsubstituted carbazol-9-yl group.

[0028] R １ ~R ５ The donor group that can be taken by is preferably a substituted or unsubstituted carbazol-9-yl group. The carbazol-9-yl group referred to here may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A, or may be substituted with a substituent selected from Substituent Group B, or may be substituted with a substituent selected from Substituent Group C, or may be substituted with a substituent selected from Substituent Group D, or may be substituted with a substituent selected from Substituent Group E. Furthermore, one or more rings may be further fused to the two benzene rings that constitute the carbazol-9-yl group. In one preferred embodiment of the present invention, １ ~R ５ The donor group represented by the formula (I) may be substituted with a group selected from Substituent Group E and is a carbazol-9-yl group which may have one or more fused rings. When a carbazol-9-yl group which does not have a fused ring is substituted, the substitution position is not particularly limited, but is preferably at least one of the 2- to 7-positions, more preferably at least one of the 3- or 6-positions, and even more preferably the 3- and 6-positions.

[0029] In one aspect of the present invention, R １ ~R ５ The donor group R can take 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 ５The ring-fused carbazol-9-yl group represented by the formula (I) may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. Preferably, the ring-fused carbazol-9-yl group is unsubstituted or substituted with a substituent selected from Substituent Group E. In one embodiment of the present invention, the ring-fused carbazol-9-yl group is unsubstituted. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group is substituted with an aryl group which may be substituted with one atom or group, or a combination of two or more groups, selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group.

[0030] 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).

[0031] The ring-fused carbazole-9-yl group is a group bonded via a nitrogen atom constituting the ring skeleton of carbazole, and has a structure in which a ring is fused to at least one of the two benzene rings constituting carbazole. The fused ring may be an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, or an aliphatic heterocycle, or may be a ring formed by further condensing these. An aromatic hydrocarbon ring or an aromatic heterocycle is preferred. An example of an aromatic hydrocarbon ring is a substituted or unsubstituted benzene ring. The benzene ring may be fused with another benzene ring or may be fused with a heterocycle such as a pyridine ring. The aromatic heterocycle refers to a ring exhibiting aromaticity that contains a heteroatom as a ring skeleton-constituting atom, and is preferably a 5- to 7-membered ring; for example, a 5-membered ring or a 6-membered ring may be employed. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring may be employed as the aromatic heterocycle. In one embodiment of the present invention, the fused ring is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole. The nitrogen atom of the pyrrole ring is preferably bonded to a substituent selected from Substituent Group E (excluding cases where the substituent is only a deuterium atom), and more preferably to an aryl group optionally substituted with an alkyl group or an aryl group. In the present invention, it is preferable to employ a carbazol-9-yl group fused to a ring having one or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, and nitrogen atoms as ring skeleton-constituting atoms. Of these, a carbazol-9-yl group fused to a benzofuro structure, a carbazol-9-yl group fused to a benzothieno structure, or a carbazol-9-yl group fused to an indolo structure can be preferably employed. In one embodiment of the present invention, the compound has at least one, for example, two or more, carbazol-9-yl groups fused to a benzofuro structure. In one embodiment of the present invention, the compound has at least one carbazol-9-yl group to which a benzothieno structure is fused, for example, two or more carbazol-9-yl groups.

[0032] Examples of the ring-fused carbazol-9-yl group include a benzofuro[2,3-a]carbazol-9-yl group, a benzofuro[3,2-a]carbazol-9-yl group, a benzofuro[2,3-b]carbazol-9-yl group, a benzofuro[3,2-b]carbazol-9-yl group, a benzofuro[2,3-c]carbazol-9-yl group, and a benzofuro[3,2-c]carbazol-9-yl group. Furthermore, as the ring-fused carbazol-9-yl group, a benzothieno[2,3-a]carbazol-9-yl group, a benzothieno[3,2-a]carbazol-9-yl group, a benzothieno[2,3-b]carbazol-9-yl group, a benzothieno[3,2-b]carbazol-9-yl group, a benzothieno[2,3-c]carbazol-9-yl group, or a benzothieno[3,2-c]carbazol-9-yl group can also be employed. Furthermore, examples of the ring-fused carbazol-9-yl group include an indolo[2,3-a]carbazol-9-yl group, an indolo[3,2-a]carbazol-9-yl group, an indolo[2,3-b]carbazol-9-yl group, an indolo[3,2-b]carbazol-9-yl group, an indolo[2,3-c]carbazol-9-yl group, and an indolo[3,2-c]carbazol-9-yl group.

[0033] When the ring-fused carbazol-9-yl group is substituted, the number of substituents is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, and may be, for example, 1 or 2. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group is substituted at either the 3- or 6-position. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has at least one substituent at the para-position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has at least one substituent only at the para-position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has substituents at all of the substitutable para-positions of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group.

[0034] In the following, R in general formula (1) １~R ５ Specific examples of donor groups that can be used are shown below. However, the donor 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, 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. D represents a deuterium atom.

[0035] D717 to D1175 are disclosed as compounds in which all hydrogen atoms present in D1 to D459 have been replaced with deuterium atoms. Phenyl groups in which D1 to D1175 are bonded to the 3-position (i.e., groups in which a metaphenylene group is further bonded to * in D1 to D1175) are disclosed as D1(m) to D1175(m). Phenyl groups in which D1 to D1175 are bonded to the 4-position (i.e., groups in which a paraphenylene group is further bonded to * in D1 to D1175) are disclosed as D1(p) to D1175(p). In a preferred embodiment of the present invention, １ ~R ５ The donor group that R can take is selected from the group consisting of D1 to D1175. １ ~R ５ The donor group that R can take is selected from the group consisting of D460 to D1175. １ ~R ５ The donor group that R can take is selected from the group consisting of D1(m) to D1175(m). １ ~R ５ The donor group that R can take is selected from the group consisting of D1(p) to D1175(p). １ ~R ５ The donor group that R can take is selected from the group consisting of D1 to D13 and D717 to D729. １ ~R ５ The donor group that R can take is selected from the group consisting of D14 to D16 and F730 to D732. １ ~R ５ The donor group that R can take is selected from the group consisting of D17 to D87 and D733 to D803. １ ~R ５ The donor group that R can take is selected from the group consisting of D88 to D123 and D804 to D839. １ ~R ５ The donor group that R can take is selected from the group consisting of D124 to D189 and D840 to D905. １ ~R ５The donor group that R can take is selected from the group consisting of D190 to D363, D452 to D459, D906 to D1079, and D1168 to D1175. １ ~R ５ The donor group that R can take is selected from the group consisting of D364 to D451 and D1080 to D1167. １ ~R ５ The donor group that can be taken by is selected from the group consisting of D460 to D716.

[0036] R in general formula (1) １ ~R ５ In one aspect of the present invention, one or more of R １ ~R ５ In one embodiment of the present invention, 1 to 3 of R １ ~R ５ In one embodiment of the present invention, one, two or three of R １ ~R ５ In a preferred embodiment of the present invention, one of R １ ~R ５ In one embodiment of the present invention, two of R １ ~R ５ In one embodiment of the present invention, at least three of R １ is a donor group. In one embodiment of the present invention, at least R ３ is a donor group. In one embodiment of the present invention, at least R ４ is a donor group. In one embodiment of the present invention, at least R ５ is a donor group. In one embodiment of the present invention, R １ In one aspect of the invention, R ３ In one aspect of the invention, R ４ In one aspect of the invention, R ５ In a preferred embodiment of the present invention, R ３ and R ５ In a preferred embodiment of the present invention, R ２ and R ５ In one aspect of the invention, R２ and R ４ In one aspect of the invention, R ３ and R ４ and R ５ In one aspect of the invention, R ２ and R ４ and R ５ Only R is a donor group. １ ~R ５ When two or more of R are donor groups, they may be the same or different. １ ~R ５ The number of hydrogen atoms or deuterium atoms among R is 0 to 2, preferably 0 or 1, for example 1, for example 0. １ ~R ５ R １ ~R ５ The number of substituted or unsubstituted aryl groups among R is 0 or 1, and preferably 1. １ ~R ５ The number of substituted or unsubstituted alkyl groups among these is 0 to 3, preferably 0 to 2, and may be 1 or 0.

[0037] In a preferred embodiment of the present invention, R １ ~R ５ Two of X are donor groups, one is a substituted or unsubstituted aryl group, and one is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, the two donor groups are the same. In one embodiment of the present invention, the two donor groups are different from each other. In one embodiment of the present invention, ５ or X ６ is N and R １ is a hydrogen atom or a deuterium atom. ５ is N and R １ is a hydrogen atom or a deuterium atom, and R ３ and R ５ is a donor group, and R ４ is a substituted or unsubstituted aryl group.５ is N and R １ is a hydrogen atom or a deuterium atom, and R ４ and R ５ is a donor group, and R ３ is a substituted or unsubstituted aryl group. ５ is N and R １ is a hydrogen atom or a deuterium atom, and R ３ and R ４ is a donor group, and R ５ is a substituted or unsubstituted aryl group. ６ is N and R １ is a hydrogen atom or a deuterium atom, and R ２ and R ５ is a donor group, and R ４ is a substituted or unsubstituted aryl group. ６ is N and R １ is a hydrogen atom or a deuterium atom, and R ４ and R ５ is a donor group, and R ２ is a substituted or unsubstituted aryl group. １ ~R ５ Three of the donor groups are donor groups, and one is a hydrogen atom or a deuterium atom. In one embodiment of the present invention, the three donor groups are the same. In one embodiment of the present invention, two of the three donor groups are the same and one is different. In one embodiment of the present invention, ５ is N and R １ is a hydrogen atom or a deuterium atom, and R ３ ~R ５ is a donor group. ６ is N and R １ is a hydrogen atom or a deuterium atom, and R ２ , R ４ and R ５ is a donor group. In one embodiment of the present invention, R １ ~R ５ In one embodiment of the present invention, one of X is a donor group, one is a substituted or unsubstituted aryl group, and two are hydrogen atoms or deuterium atoms.５ is N and R １ and R ３ is a hydrogen atom or a deuterium atom, and R ４ is a substituted or unsubstituted aryl group, and R ５ is a donor group. ５ is N and R １ and R ３ is a hydrogen atom or a deuterium atom, and R ４ is a donor group, and R ５ is a substituted or unsubstituted aryl group. ５ is N and R １ and R ５ is a hydrogen atom or a deuterium atom, and R ３ is a donor group, and R ４ is a substituted or unsubstituted aryl group. ５ is N and R １ and R ４ is a hydrogen atom or a deuterium atom, and R ３ is a donor group, and R ５ is a substituted or unsubstituted aryl group. ５ is N and R １ is a donor group, and R ３ and R ５ is a hydrogen atom or a deuterium atom, and R ４ is a substituted or unsubstituted aryl group. ５ is N and R １ is a donor group, and R ３ and R ４ is a hydrogen atom or a deuterium atom, and R ５ is a substituted or unsubstituted aryl group. In a preferred embodiment of the present invention, R １ ~R ５ In one embodiment of the present invention, two of X are donor groups and two are hydrogen atoms or deuterium atoms. ５ is N and R １ and R ４ is a hydrogen atom or a deuterium atom, and R ３ and R ５is a donor group. ５ is N and R １ and R ５ is a hydrogen atom or a deuterium atom, and R ３ and R ４ is a donor group. ５ is N and R １ and R ３ is a hydrogen atom or a deuterium atom, and R ４ and R ５ is a donor group. In a preferred embodiment of the present invention, X ６ is N and R １ and R ４ is a hydrogen atom or a deuterium atom, and R ２ and R ５ is a donor group. ６ is N and R １ and R ２ is a hydrogen atom or a deuterium atom, and R ４ and R ５ is a donor group. In one embodiment of the present invention, R １ ~R ５ In one embodiment of the present invention, one of X is a donor group and three are hydrogen atoms or deuterium atoms. ５ is N and R １ , R ３ and R ４ is a hydrogen atom or a deuterium atom, and R ５ is a donor group. ５ is N and R １ , R ３ and R ５ is a hydrogen atom or a deuterium atom, and R ４ is a donor group. ５ is N and R １ , R ４ and R ５ is a hydrogen atom or a deuterium atom, and R ３ is a donor group. ５ is N and R １ is a donor group, and R ３ , R ４and R ５ is a hydrogen atom or a deuterium atom. ３ ~R ５ are each independently a substituted or unsubstituted aryl group or a donor group. ３ ~R ５ In a preferred embodiment of the present invention, two of R are donor groups and one is a substituted or unsubstituted aryl group. ３ and R ５ is a donor group, and R ４ is a substituted or unsubstituted aryl group. ３ , R ４ and R ５ is a donor group. In one embodiment of the present invention, R ２ , R ４ and R ５ is a substituted or unsubstituted aryl group or a donor group. ２ , R ４ and R ５ In a preferred embodiment of the present invention, two of R are donor groups and one is a substituted or unsubstituted aryl group. ２ and R ５ is a donor group, and R ４ is a substituted or unsubstituted aryl group. ２ , R ４ and R ５ is a donor group.

[0038] Ar in general formula (1) １ and Ar ２The heteroaryl group represented by the formula (I) may be a monocyclic 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 pyridine ring, a pyrimidine ring, and a pyrrole ring, and these rings may be further fused with another ring. Specific examples of the heteroaryl group include a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a carbazol-9-yl group, a carbazol-1-yl group, a carbazol-2-yl group, a carbazol-3-yl group, and a carbazol-4-yl group. The number of atoms constituting the ring skeleton of the heteroaryl group is preferably 4 to 40, more preferably 5 to 20, and may be selected within a range of 5 to 16, or may be selected within a range of 5 to 12. Ar in general formula (1) １ and Ar ２ At least one of the Ar groups is a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom. That is, it is a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom, and is bonded via the nitrogen atom, which is one of the ring skeleton-constituting atoms. A typical example of such a group is a substituted or unsubstituted pyrrol-1-yl group, preferably a substituted or unsubstituted ring-fused pyrrol-1-yl group, and more preferably a substituted or unsubstituted carbazol-9-yl group, and the carbazole skeleton may be further fused with a ring. １ and Ar ２ Specific examples of the substituted or unsubstituted heteroaryl group bonded via a nitrogen atom, which may be at least one of the groups represented by the formula (I) above, include D1 to D1175. １ and Ar ２ In one embodiment of the present invention, the group represented by at least one of Ar １ and Ar ２ In one embodiment of the present invention, the group represented by at least one of Ar １ and Ar ２In one embodiment of the present invention, the group taken by at least one of Ar １ and Ar ２ In one embodiment of the present invention, the group taken by at least one of Ar １ and Ar ２ In one embodiment of the present invention, the group taken by at least one of Ar １ and Ar ２ The group taken by at least one of Ar is selected from the group consisting of D190 to D363, D452 to D459, D906 to D1079, and D1168 to D1175. １ and Ar ２ In one embodiment of the present invention, the group taken by at least one of Ar １ and Ar ２ In one embodiment of the present invention, the group taken by at least one of Ar １ and Ar ２ are each independently a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom. １ and Ar ２ is a substituted or unsubstituted heteroaryl group bonded at a nitrogen atom, and has the same structure. １ is a substituted or unsubstituted heteroaryl group in which only one nitrogen atom is bonded, ２ is a substituted or unsubstituted aryl group.

[0039] L in general formula (1) １ represents a single bond or a divalent linking group. Examples of the divalent linking group include a substituted or unsubstituted arylene group and a substituted or unsubstituted heteroarylene group. In a preferred embodiment of the present invention, L １ is a single bond. In one aspect of the present invention, L １ is a substituted or unsubstituted arylene group.１ is a substituted or unsubstituted heteroarylene group. The aryl moiety constituting the arylene group is １ ~R ５ The description of the aryl group and the preferred range thereof can be referred to in the section on the heteroarylene group. Examples of the heteroarylene group include a linking group in which at least one of the ring skeleton carbon atoms constituting the arylene group is substituted with a nitrogen atom. １ However, the L that can be used in the present invention is １ is not to be construed as being limited by these specific examples. In the following specific examples, methyl groups are omitted. Therefore, for example, L3 to L5 are substituted with methyl groups. * indicates the bonding position. L1 is a single bond.

[0040]

[0041] All hydrogen atoms in L2 to L21 are replaced with deuterium atoms, and L22 to L41 are disclosed as such. １ is selected from the group consisting of L1 to L7, L22 to L27. １ is selected from the group consisting of L2 to L7, L22 to L27. １ is selected from the group consisting of L1, L8 to L13, L20, L21, L28 to L33, L40, and L41. １ is selected from the group consisting of L8 to L13, L20, L21, L28 to L33, L40, and L41. １ is selected from the group consisting of L1, L14 to L19, and L34 to L39. １ is selected from the group consisting of L14 to L19, L34 to L39.

[0042] In a preferred embodiment of the present invention, X １ ~X ３ , X ５ is N and L １ is a single bond, and Ar １ and Ar ２are each independently a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded via a nitrogen atom, and R １ , R ３ ~R ５ two of the groups are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), one is a substituted or unsubstituted aryl group, and one (preferably R １ ) is a hydrogen atom or a deuterium atom. １ ~X ３ , X ５ is N and L １ is a single bond, and Ar １ is a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded at a nitrogen atom, and Ar ２ is a substituted or unsubstituted aryl group, and R １ , R ３ ~R ５ two of the groups are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), one is a substituted or unsubstituted aryl group, and one (preferably R １ ) is a hydrogen atom or a deuterium atom. １ ~X ３ , X ５ is N and L １ is a single bond, and Ar １ and Ar ２ are each independently a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded via a nitrogen atom, and R １ , R ３ ~R ５ Three of the groups are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), and one of the groups (preferably R １ ) is a hydrogen atom or a deuterium atom. １ ~X ３ , X ５ is N and L １ is a single bond, and Ar １is a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded at a nitrogen atom, and Ar ２ is a substituted or unsubstituted aryl group, and R １ , R ３ ~R ５ Three of the groups are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), and one of the groups (preferably R １ ) is a hydrogen atom or a deuterium atom. １ ~X ３ , X ６ is N and L １ is a single bond, and Ar １ and Ar ２ are each independently a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded via a nitrogen atom, and R １ , R ２ , R ４ , R ５ Among these, two or three are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), and one or two (preferably at least R １ ) is a hydrogen atom or a deuterium atom, and 0 to 1 is a substituted or unsubstituted aryl group. １ ~X ３ , X ６ is N and L １ is a single bond, and Ar １ is a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded at a nitrogen atom, and Ar ２ is a substituted or unsubstituted aryl group, and R １ , R ２ , R ４ , R ５ Among these, two or three are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), and one or two (preferably at least R １ ) is a hydrogen atom or a deuterium atom, and 0 to 1 is a substituted or unsubstituted aryl group. １ ~X ３ , X６ is N and L １ is a single bond, and Ar １ and Ar ２ are each independently a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded via a nitrogen atom, and R １ , R ２ , R ４ , R ５ two of the groups are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), one is a substituted or unsubstituted aryl group, and one (preferably at least R １ ) is a hydrogen atom or a deuterium atom. １ ~X ３ , X ６ is N and L １ is a single bond, and Ar １ is a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded at a nitrogen atom, and Ar ２ is a substituted or unsubstituted aryl group, and R １ , R ２ , R ４ , R ５ two of the groups are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), one is a substituted or unsubstituted aryl group, and one (preferably at least R １ ) is a hydrogen atom or a deuterium atom. １ ~X ３ , X ６ is N and L １ is a single bond, and Ar １ and Ar ２ are each independently a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded via a nitrogen atom, and R １ , R ２ , R ４ , R ５ two of the groups are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), and two of the groups (preferably at least R １) is a hydrogen atom or a deuterium atom. １ ~X ３ , X ６ is N and L １ is a single bond, and Ar １ is a substituted or unsubstituted heteroaryl group (preferably a substituted or unsubstituted carbazol-9-yl group) bonded at a nitrogen atom, and Ar ２ is a substituted or unsubstituted aryl group, and R １ , R ２ , R ４ , R ５ two of the groups are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), and two of the groups (preferably at least R １ ) is a hydrogen atom or a deuterium atom.

[0043] 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.

[0044] In the present specification, the term "substituent group A" refers to a deuterium atom, a hydroxyl group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an alkylthio group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), an arylthio group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), It means one atom or group, or a combination of two or more groups, selected from the group consisting of heteroarylthio groups (e.g., having 5 to 30 atoms constituting the ring skeleton), 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 7 to 40 carbon atoms), heteroaryloxycarbonyl groups (e.g., having 5 to 40 carbon atoms), silyl groups (e.g., trialkylsilyl groups having 1 to 40 carbon atoms), and nitro groups. As used herein, "substituent group B" refers to one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring atoms), a heteroaryloxy group (e.g., having 5 to 30 ring atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms). As used herein, "substituent group C" refers to one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), a heteroaryl group (e.g., having 5 to 20 ring atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms). As used herein, the term "substituent group D" refers to one atom or group, or a combination of two or more groups, selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), and a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms).As used herein, "substituent group E" refers to one atom or group, or a combination of two or more, selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), and an aryl group (e.g., having 6 to 22 carbon atoms). In the present specification, when "substituted or unsubstituted" or "optionally substituted" is described, the substituent may be selected, for example, from substituent group A, from substituent group B, from substituent group C, from substituent group D, or from substituent group E.

[0045] Specific examples of compounds represented by general formula (1) are shown in Tables 1 to 5 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, R ３ ~R ５ The structure of each compound is individually shown by specifying each compound. １ and Ar ２ is a deuterated carbazolyl group (D717), and X １ ~X ３ is a nitrogen atom (N), and L １ is a single bond, and X ５ is N and R １ is a hydrogen atom, and R ３ ~R ５ The structures in which is a group specified in Table 1 are shown individually as the structures of compounds 1 to 1175.

[0046] In Table 2, each row contains R ３ ~R ５ For example, in the column of compounds 1 to 1175 in Table 2, R ４ is fixed to Ar1, and R ３ and R ５ The compounds in which both are D1 to D1175 are designated as compounds 1 to 1175, respectively. ３ and R ５In other words, the column of compounds 1 to 1175 in Table 2 shows all compounds 1 to 1175 specified in Table 1 in one column. Similarly, in the column of compounds 1176 to 2350 in Table 2, R ４ is fixed to Ar2, and R ３ and R ５ The compounds having both D1 to D1175 are designated as compounds 1176 to 2350. Compounds 2351 to 1015655 in Table 2 are also identified in the same manner.

[0047] Next, specific examples of compounds having a structure represented by the following general formula (1b) are shown in Table 3. In Table 3, the structure of each compound is shown in the same manner as in Table 2.

[0048] Next, specific examples of compounds having a structure represented by the following general formula (1c) are shown in Table 4. In Table 4, the structure of each compound is shown in the same manner as in Table 2.

[0049] In Tables 1 to 4, Ar in general formula (1) １ and Ar ２ The structures in which Ar is a deuterated carbazolyl group (D717) were identified as the structures of compounds 1 to 2101810. Table 5 shows the structures of compounds 1 to 2101810. １ and Ar ２The compounds in which the Ar group is changed as shown in Table 5 are listed in order in a table format. In Table 5, in order to make the correspondence easier to understand, compounds 1 to 2101810 are also listed in the first row. In the second row of Table 5, for example, compound 1(1) is the compound 1 with Ar ２ In addition, compound 2(1) is a compound having a structure in which Ar is substituted with Ar in compound 2. ２ The compound 2031310(1) is a compound having a structure in which Ar is substituted with Ar in the compound 2101810. ２ The compounds 1(2) to 2101810(2) in the third row of Table 5 and the compounds in the subsequent rows are also specified in the same manner. １ ~X ３ are all nitrogen atoms (N), and L １ is a single bond, and R １ is a hydrogen atom.

[0050] All compounds identified by the above numbers are considered to be individually disclosed. In addition, when rotamers exist among the specific examples of the compounds, the mixture of rotamers and each separated rotamer are also considered to be disclosed in the present specification.

[0051] In one embodiment of the present invention, a compound is selected from compound group α consisting of compounds 1 to 2101810 and compounds 1(n) to 2101810(n) [where n is 1 to 1813]. In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above [4]. In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above [4]. In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above [5]. In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above [6]. In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above [7]. In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above [8]. In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above [9]. In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above

[10] . In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above

[11] . In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above

[12] . In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above

[13] . In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above

[17] . In one embodiment of the present invention, a compound is selected from compound group β consisting of compounds 1 to 1015655 and compounds 1(n) to 1015655(n) [where n is 1 to 1813]. In one embodiment of the present invention, a compound is selected from compound group β that satisfies the above [4]. In one embodiment of the present invention, a compound is selected from compound group β that satisfies the above [5]. In one embodiment of the present invention, a compound is selected from compound group β that satisfies the above [6]. In one embodiment of the present invention, a compound is selected from compound group β that satisfies the above [7]. In one embodiment of the present invention, a compound is selected from compound group β that satisfies the above [8]. In one embodiment of the present invention, a compound is selected from compound group β that satisfies the above [9]. In one embodiment of the present invention, a compound is selected from compound group β that satisfies the above

[10] .In one embodiment of the present invention, a compound is selected from compound group β that satisfies the above

[11] . In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above

[12] . In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above

[13] . In one embodiment of the present invention, a compound is selected from compound group β that satisfies the above

[17] . In one embodiment of the present invention, a compound is selected from compound group γ consisting of compounds 1015656 to 2031310 and compounds 1015656(n) to 2031310(n) [where n is 1 to 1813]. In one embodiment of the present invention, a compound is selected from compound group γ that satisfies the above [4]. In one embodiment of the present invention, a compound is selected from compound group γ that satisfies the above [5]. In one embodiment of the present invention, a compound is selected from compound group γ that satisfies the above [6]. In one embodiment of the present invention, a compound is selected from compound group γ that satisfies the above [7]. In one embodiment of the present invention, a compound is selected from compound group γ that satisfies the above [8]. In one embodiment of the present invention, a compound is selected from compound group γ that satisfies the above

[10] . In one embodiment of the present invention, a compound is selected from compound group γ that satisfies the above

[11] . In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above

[12] . In one embodiment of the present invention, a compound is selected from compound group α that satisfies the above

[13] . In one embodiment of the present invention, a compound is selected from compound group γ that satisfies the above

[17] . In one embodiment of the present invention, a compound is selected from compound group δ consisting of compounds 2031311 to 2101810 and compounds 2031311(n) to 2101810(n) [where n is 1 to 1813]. In one embodiment of the present invention, a compound is selected from compound group δ that satisfies the above [5]. In one embodiment of the present invention, a compound is selected from compound group δ that satisfies the above [9]. In one embodiment of the present invention, a compound is selected from compound group δ that satisfies the above

[13] . In one embodiment of the present invention, a compound is selected from compound group δ that satisfies the above

[17] .

[0052] In one embodiment of the present invention, the compound represented by general formula (1) is selected from the following group of compounds:

[0053] In one embodiment of the present invention, the compound represented by general formula (1) is selected from the following group of compounds:

[0054] In a preferred embodiment of the present invention, the compound represented by general formula (1) is selected from the following group of compounds:

[0055] In one embodiment of the present invention, the compound represented by general formula (1) is selected from the following group of compounds:

[0056] The molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 900 or less, when it is intended to use an organic layer containing the compound represented by general formula (1) as a film formed by a vapor deposition method. 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) may be formed into a film by a coating method regardless of its molecular weight. By using a 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 organic solvents. Therefore, the compound represented by general formula (1) is easy to apply a coating method to and is also 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] In some embodiments, the compound represented by general formula (1) is a light-emitting material. In some embodiments, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence. In some embodiments of the present disclosure, the compound represented by general formula (1), when excited by thermal or electronic means, can emit light in the UV region, the blue, green, yellow, orange, or red region of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm), or the near-infrared region. In some embodiments of the present disclosure, the compound represented by general formula (1), when excited by thermal or electronic means, can emit light in the red or orange region of the visible spectrum (e.g., about 620 nm to about 780 nm, about 650 nm). In some embodiments of the present disclosure, the compound represented by general formula (1), when excited by thermal or electronic means, can emit light in the orange or yellow region of the visible spectrum (e.g., about 570 nm to about 620 nm, about 590 nm, about 570 nm). In some embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the green region of the visible spectrum (e.g., about 490 nm to about 575 nm, about 510 nm) when excited by thermal or electronic means. In some embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm, about 475 nm) when excited by thermal or electronic means. In some embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the ultraviolet region of the spectrum (e.g., 280-400 nm) when excited by thermal or electronic means. In some embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the infrared region of the spectrum (e.g., 780 nm to 2 μm) when excited by thermal or electronic means. In some embodiments of the present disclosure, the compound represented by general formula (1) can be used to fabricate organic semiconductor devices. The organic semiconductor element referred to here may be an organic optical element in which light is mediated, or an organic element in which light is not mediated.The organic optical element may be an organic light-emitting element that emits light, an organic light-receiving element that receives light, or an element that causes energy transfer by light within the element. In some embodiments of the present disclosure, an organic optical element such as an organic electroluminescence element or a solid-state imaging element (e.g., a CMOS image sensor) can be fabricated using a compound represented by general formula (1). In some embodiments of the present disclosure, a CMOS (complementary metal oxide semiconductor) or the like can be fabricated using a compound represented by general formula (1).

[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 ＳＴThe quantum yield of the compound represented by formula (1) is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV. In certain embodiments, the compound represented by formula (1) exhibits a quantum yield of greater than 25%, e.g., about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.

[0065] [Method for Synthesizing Compounds Represented by General Formula (1)] Compounds represented by general formula (1) include novel compounds. Compounds represented by general formula (1) can be synthesized by combining known reactions. For example, among the compounds represented by general formula (1), a compound having a structure in which a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted aryl group (e.g., a phenyl group), and a triazyl group substituted with two substituted or unsubstituted carbazolyl groups are bonded to a pyridine ring can be synthesized by introducing a triazyl group having two substituted or unsubstituted carbazolyl groups into a pyridine derivative having a substituted or unsubstituted aryl group and a halogen atom, and then reacting the resulting compound with a substituted or unsubstituted carbazole. 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 the compound of the present invention is applied to a surface, and a film is formed after removing the solvent. Examples of wet processes include, but are not limited to, spin coating, slit coating, inkjet (spray) printing, gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In some embodiments, a substituent (e.g., an alkyl group) that increases the solubility in organic solvents can be introduced into the compound contained in the composition. In some embodiments, a film containing the compound of the present invention can be formed by a dry process. In some embodiments, a vacuum deposition method can be used as the dry process, but is not limited thereto. When using a vacuum deposition method, the compounds constituting the film may be co-deposited from separate deposition sources, or may be co-deposited from a single deposition source containing a mixture of compounds. When a single deposition source is used, a mixed powder of compound powders may be used, a compression molded product obtained by compressing the mixed powder may be used, or a mixture of the compounds may be used by heating, melting, and cooling the melted mixture. In some embodiments, co-deposition can be performed under conditions where the deposition rates (weight loss rates) of multiple compounds contained in a single deposition source are the same or nearly the same, thereby forming a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source. A film having a desired composition ratio can be easily formed by mixing multiple compounds in the same composition ratio as the composition ratio of the film to be formed and using the resulting deposition source. In some embodiments, a temperature at which the weight loss rates of the co-deposited compounds are the same can be identified, and this temperature can be used as the temperature during co-deposition.

[0068] [Examples of Use of Compounds Represented by General Formula (1)] Compounds represented by general formula (1) are useful as materials for organic light-emitting devices. They are particularly preferably used in organic light-emitting diodes and the like. Organic Light-Emitting Diodes: One aspect of the present invention relates to the use of compounds represented by general formula (1) of the present invention as light-emitting materials for organic light-emitting devices. In some embodiments, compounds represented by general formula (1) of the present invention can be effectively used as light-emitting materials in the light-emitting layer of organic light-emitting devices. In some embodiments, compounds represented by general formula (1) include delayed fluorescence (delayed fluorescent material) that emits delayed fluorescence. In some embodiments, the present invention provides a delayed fluorescent material having a structure represented by general formula (1). In some embodiments, the present invention relates to the use of compounds represented by general formula (1) as delayed fluorescent materials. In some embodiments, the present invention can be used as a host material and can be used together with one or more light-emitting materials, which may be fluorescent materials, phosphorescent materials, or TADF. In some embodiments, the compounds represented by general formula (1) can also be used as hole-transporting materials. In some embodiments, the compounds represented by general formula (1) can be used as electron-transporting materials. In some embodiments, the present invention relates to a method for producing delayed fluorescence from a compound represented by general formula (1). In some embodiments, an organic light-emitting device comprising the compound as an emitting material emits delayed fluorescence and exhibits high light emission efficiency. In some embodiments, the emitting layer comprises a compound represented by general formula (1), and the compound represented by general formula (1) is aligned parallel to the substrate. In some embodiments, the substrate is a film-forming surface. In some embodiments, the orientation of the compound represented by general formula (1) relative to the film-forming surface affects or determines the propagation direction of light emitted by the aligned compound. In some embodiments, aligning the propagation direction of light emitted by the compound represented by general formula (1) improves the light extraction efficiency from the emitting layer. One aspect of the present invention relates to an organic light-emitting device. In some embodiments, the organic light-emitting device comprises an emitting layer. In some embodiments, the emitting layer comprises a compound represented by general formula (1) as an emitting material. In some embodiments, the organic light-emitting device is an organic photoluminescence device (organic PL device).In one embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device). In one embodiment, the compound represented by general formula (1) assists the light emission of other light-emitting materials contained in the light-emitting layer (as a so-called assist dopant). In one embodiment, the compound represented by general formula (1) contained in the light-emitting layer has its lowest excited singlet energy level, which is between the lowest excited singlet energy level of the host material contained in the light-emitting layer and the lowest excited singlet energy level of the other light-emitting materials contained in the light-emitting layer. In one embodiment, the organic light-emitting device includes at least one light-emitting layer. In one embodiment, the organic electroluminescence device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In one embodiment, the organic layer includes at least an light-emitting layer. In one embodiment, the organic layer includes only an light-emitting layer. In one embodiment, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole-transporting layer, a hole-injecting layer, an electron-blocking layer, a hole-blocking layer, an electron-injecting layer, an electron-transporting layer, and an exciton-blocking layer. In some embodiments, the hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function.

[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; that is, any host material capable of achieving high light emission efficiency can be used in the present invention without particular limitations. In some embodiments, light emission occurs in the light-emitting material in the light-emitting layer of the device of the present invention. In some embodiments, the emitted light includes both fluorescence and delayed fluorescence. In some embodiments, the emitted light includes light emitted from the host material. In some embodiments, the emitted light consists of light emitted from the host material. In some embodiments, the emitted light includes light emitted from the compound represented by general formula (1) and light emitted from the host material. In some embodiments, a TADF molecule and a host material are used. In some embodiments, TADF is an assist dopant, and has a lower excited singlet energy than the host material in the light-emitting layer and a higher excited singlet energy than the light-emitting material in the light-emitting layer.

[0070] When a compound represented by general formula (1) is used as an assist dopant, various compounds can be used as the luminescent material (preferably a fluorescent material). Examples of such luminescent materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, and derivatives containing metals (Al, Zn). These exemplary skeletons may or may not have a substituent. These exemplary skeletons may also be combined. Examples of luminescent materials that can be used in combination with an assist dopant having a structure represented by general formula (1) are listed below.

[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 ４ At 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 ７and 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 ８ 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. 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 １In 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 , 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 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-R９ , 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 R ８ , 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-R９ , 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 ２are 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-R ６ , 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 ５are 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 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, 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 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 ３R 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 R ３ 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 Z２ , 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; Z ３ 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 ４each 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 １６ and 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 R３ 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 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 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 Z６ 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 , Z７ 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 Z １ , 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. １and 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 １１and 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 , R ７１ 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 , R７８ 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 ５ represents 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 , R１２１ 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 , R １３０ 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 R６ , 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-R ４ , 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 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 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 １８are 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, R １ ~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.

[0122] In one aspect of the present invention, R ３ and R ６ In one embodiment of the present invention, at least one of R ３ and R ６ are both substituents. In one aspect of the present invention, R ３ and R ６ is one group selected from the group consisting of alkyl groups and aryl groups, or a group in which two or more groups are combined. ８ and R １２ In one embodiment of the present invention, the compound is represented by the following general formula (1a).

[0123] In the general formula (22a), Ar １ ~Ar ４ R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. ４１ and R ４２each independently represents a substituted or unsubstituted alkyl group. m1 and m2 each independently represents an integer of 0 to 5, n1 and n3 each independently represents an integer of 0 to 4, and n2 and n4 each independently represents an integer of 0 to 3. A １ , A ２ each independently represents a hydrogen atom, a deuterium atom, or a substituent. For a detailed description of the compounds represented by general formula (22) or general formula (22a), as well as preferred ranges and specific examples, reference can be made to paragraphs

[0010] to

[0119] of WO2022 / 270354A1, which is incorporated herein by reference as part of this specification. For example, the following compounds can be mentioned:

[0124] In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 0.1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 50% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 20% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 10% by weight or less. In some embodiments, the host material in the light-emitting layer is an organic compound having hole-transporting and electron-transporting functions. In some embodiments, the host material in the light-emitting layer is an organic compound that prevents the wavelength of emitted light from increasing. In some embodiments, the host material in the light-emitting layer is an organic compound having a high glass transition temperature.

[0125] 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 the present invention may be any of the multiple TADF compounds contained in the emitting layer. In some embodiments, the emitting layer may be composed of a material selected from the group consisting of a host material, an assist dopant, and an emitting material. In some embodiments, the emitting layer does not contain a metal element.In some embodiments, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. When the light-emitting layer contains a TADF material other than the compound of the present invention, the TADF material can be a known delayed fluorescent material. Preferred delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 011955, and paragraph 0008 of WO2013 / 081088. to 0071 and 0118 to 0133, paragraphs 0009 to 0046 and 0093 to 0134 of JP 2013-256490 A, paragraphs 0008 to 0020 and 0038 to 0040 of JP 2013-116975 A, paragraphs 0007 to 0032 and 0079 to 0084 of WO 2013 / 133359 A, paragraph 0 of WO 2013 / 161437 A JP-A-2014-9352, paragraphs 0007 to 0041 and 0060 to 0069, JP-A-2014-9224, paragraphs 0008 to 0048 and 0067 to 0076, JP-A-2017-119663, paragraphs 0013 to 0025, JP-A-2017-119664, paragraphs 0013 to 0026, JP-A-2017-119665, Compounds encompassed by the general formulas described in paragraphs 0012 to 0025 of JP-A No. 017-222623, paragraphs 0010 to 0050 of JP-A No. 2017-226838, paragraphs 0012 to 0043 of JP-A No. 2018-100411, and paragraphs 0016 to 0044 of WO2018 / 047853, particularly exemplified compounds, which are capable of emitting delayed fluorescence, are included.Further, here, the following patent documents are disclosed: JP 2013-253121 A, WO 2013 / 133359 A, WO 2014 / 034535 A, WO 2014 / 115743 A, WO 2014 / 122895 A, WO 2014 / 126200 A, WO 2014 / 136758 A, WO 2014 / 133121 A, WO 20 14 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008 580 publication, WO2014 / 203840 publication, WO2015 / 002213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP2015-129240A, WO2015 / 129714, WO2015 / 129715, WO2015 / 13350 Preferably, the luminescent materials capable of emitting delayed fluorescence are those described in WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541. The above publications described in this paragraph are incorporated herein by reference.

[0126] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0127] 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.

[0128] 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.

[0129] 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.

[0130] 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:

[0131]

[0132] Next, examples of preferred compounds that can be used as the electron injection material will be given.

[0133] 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.

[0134] 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.

[0135]

[0136] 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.

[0137]

[0138] 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.

[0139] 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.

[0140]

[0141] 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.

[0142]

[0143] 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.

[0144]

[0145] 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.

[0146] 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).

[0147] 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.

[0148] 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.

[0149] 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 planarizing film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the cell panel from the mother panel.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] 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.

[0154] 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.

[0155] 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.

[0156] The features of the present invention will be explained in more detail below with reference to synthesis examples and examples. The materials, processing details, processing procedures, etc. shown below can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. The emission characteristics were evaluated using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334). The HOMO and LUMO energies were measured by atmospheric photoelectron spectroscopy (Riken Keiki AC-3, etc.). In the synthesis examples below, compounds represented by general formula (1) were synthesized.

[0157] (Synthesis Example 1) Synthesis of Compound 46542

[0158] Compound a: Under a nitrogen atmosphere, a solution of (phenyl-d5)boronic acid (3.16 g, 24.90 mmol), 2,4-difluoro-3-iodopyridine (5.00 g, 20.75 mmol), potassium carbonate (8.60 g, 62.25 mmol, 2 M aqueous solution), and tetrakis(triphenylphosphine)palladium(0) (3 mol%) dissolved in tetrahydrofuran (200 mL) and distilled water was refluxed for 12 hours. The reaction solution was cooled to room temperature and extracted with methylene chloride and distilled water, and the organic layer was then distilled off using an evaporator. The resulting residue was purified by silica gel column chromatography using a 1:1 mixed solvent of chloroform and hexane as an eluent to obtain compound a (2.80 g, 14.27 mmol, yield 68.8%) as a white solid. 1 H NMR (400 MH Z , CDCl3) δ8.1675 (dd, J = 8.0 H Z , 6.0 H Z , 1H), 7.0725 (dd, J = 8.2 H Z , 5.2 H Z , 1H) ASAP MS spectrum analysis: C11H2D5F2N: Calculated 196, Observed 197.

[0159]

[0160] Compound b: Under a nitrogen stream, a 1 M lithium diisopropylamide solution (3.57 mL, 3.57 mmol) was added portionwise to a tetrahydrofuran solution (15 mL) of compound a (0.70 g, 3.57 mmol) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane (0.66 g, 3.57 mmol) at −85° C. After 10 minutes, the mixture was warmed to −75° C., stirred for 1 hour, and then slowly returned to room temperature. To this mixture, 9,9'-(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole-1,2,3,4,5,6,7,8-d8) (1.98 g, 4.28 mmol), 2 M aqueous potassium carbonate solution (2.68 mL, 5.35 mmol), tetrahydrofuran (100 mL), and tetrakis(triphenylphosphine)palladium(0) (0.12 g, 0.11 mmol) were added, and the mixture was heated to reflux for 12 hours. The reaction solution was returned to room temperature, and water was added to quench the reaction. The mixture was then extracted with chloroform, and the solvent was removed using an evaporator. The resulting residue was purified by silica gel column chromatography using a 1:1 mixed solvent of hexane and toluene as an eluent to obtain compound b (1.00 g, 1.61 mmol, yield 45.1%) as a white solid. 1 H NMR (400 MH Z , CDCl3) δ 9.3635 (d, J = 9.2 H Z , 1H). ASAP MS spectrum analysis: C38HD21F2N6: Calculated 621, Observed 622.

[0161]

[0162] Compound 46542: Under a nitrogen stream, a dimethylformamide solution (50 mL) containing 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.76 g, 4.34 mmol), potassium carbonate (0.80 g, 5.79 mmol), and compound b (0.9 g, 1.45 mmol) was stirred overnight at 120°C. The reaction mixture was returned to room temperature, and a saturated ammonium chloride solution was added to terminate the reaction. The mixture was then extracted with chloroform, and the solvent was removed using an evaporator. The resulting residue was purified by silica gel column chromatography using a mixed solvent of toluene and hexane as an eluent to obtain compound 46542 (0.83 g, 0.89 mmol, yield 61.5%). 1 H NMR (400 MH Z , CDCl3) δ 9.632 (s, 1H). ASAP MS spectral analysis: C62HD37N8: Calcd 931, Found 932.

[0163] (Synthesis Example 2) Synthesis of Compound 46542 (40)

[0164] Compound c: Under a nitrogen stream, a 1 M lithium diisopropylamide solution (5.10 mL, 5.10 mmol) was added portionwise to a tetrahydrofuran solution (15 mL) of compound a (1.00 g, 5.09 mmol) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane (0.95 g, 5.10 mmol) at −85° C. After 10 minutes, the mixture was warmed to −75° C., stirred for 1 hour, and then slowly returned to room temperature. To this mixture, 9-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d (2.26 g, 6.11 mmol), 2 M aqueous potassium carbonate solution (3.82 mL, 7.64 mmol), tetrahydrofuran (60 mL), and tetrakis(triphenylphosphine)palladium(0) (0.18 g, 0.15 mmol) were added, and the mixture was heated to reflux for 12 hours. The reaction solution was returned to room temperature, and water was added to quench the reaction. The mixture was then extracted with chloroform, and the solvent was removed using an evaporator. The resulting residue was purified by silica gel column chromatography using a 1:1 mixed solvent of hexane and toluene as an eluent to obtain compound c (2.40 g, 4.53 mmol, yield 89.0%) as a white solid. 1 H NMR (400 MH Z , CDCl3) δ 9.34 (d, J = 9.2 H Z , 1H). ASAP MS spectrum analysis: C32HD18F2N: Calculated 529, Found 530.

[0165]

[0166] Compound 46542 (40) Under a nitrogen stream, a dimethylformamide solution (50 mL) containing 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.50 g, 8.50 mmol), potassium carbonate (1.57 g, 11.33 mmol), and compound c (1.5 g, 2.83 mmol) was stirred overnight at 120°C. The reaction mixture was returned to room temperature, and saturated ammonium chloride solution was added to terminate the reaction. The mixture was then extracted with chloroform, and the solvent was removed using an evaporator. The resulting residue was purified by silica gel column chromatography using a mixed solvent of toluene and hexane as an eluent to obtain compound 46542 (40) (2.20 g, 2.62 mmol, yield 92.5%). 1 H NMR (400 MH Z , CDCl3) δ 9.725 (s, 1H). ASAP MS spectral analysis: C56HD34N7: Calcd 839, Found 840.

[0167] (Comparative Synthesis Example 1) Synthesis of Comparative Compound 2

[0168] Compound d: Under a nitrogen stream, at −85°C, a 1 M diisopropylamide lithium solution (5.10 mL, 5.10 mmol) was added portionwise to a tetrahydrofuran solution (15 mL) of compound a (1.0 g, 5.10 mmol) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane (0.95 g, 5.10 mmol). After 10 minutes, the mixture was heated to −75°C, stirred for 1 hour, and then slowly returned to room temperature. To this mixture were added 2-chloro-4,6-bis(phenyl-d5)-1,3,5-triazine (1.56 g, 5.60 mmol), 2 M aqueous potassium carbonate solution (3.82 mL, 7.64 mmol), tetrahydrofuran (20 mL), and tetrakis(triphenylphosphine)palladium(0) (0.18 g, 0.15 mmol), and the mixture was heated to reflux for 12 hours. The reaction solution was returned to room temperature, water was added to stop the reaction, and then the solution was extracted with chloroform and the solvent was removed using an evaporator. The resulting residue was purified by silica gel column chromatography using a 1:1 mixed solvent of hexane and toluene to obtain compound d (2.00 g, 4.57 mmol, yield 89.8%) as a white solid. 1 H NMR (400 MH Z , CDCl3) δ 9.34 (d, J = 9.2 H Z , 1H). ASAP MS spectrum analysis: C26HD15F2N: Calcd 437, Observed 438.

[0169]

[0170] Comparative Compound 2: Under a nitrogen stream, a dimethylformamide solution (50 mL) containing 9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.80 g, 10.29 mmol), potassium carbonate (1.90 g, 13.71 mmol), and compound d (1.5 g, 3.43 mmol) was stirred overnight at 120°C. The reaction mixture was returned to room temperature, and a saturated ammonium chloride solution was added to terminate the reaction. The mixture was then extracted with chloroform, and the solvent was removed using an evaporator. The resulting residue was purified by silica gel column chromatography using a mixed solvent of toluene and hexane as an eluent to obtain comparative compound 2 (2.45 g, 3.28 mmol, yield 95.5%). 1 H NMR (400 MH Z , CDCl3) δ 9.705 (s, 1H). ASAP MS spectral analysis: C50HD31N6: Calcd 747, Found 748.

[0171] (Synthesis Example 3) Synthesis of Compound 38317 (40)

[0172] Compound e: 2-([1,1':3',1'-terphenyl]-5'-yl-2,2'',3,3'',4,4'',5,5'',6,6''-d10)-4,4,5,5-tetramethyl-1,3,2-dioxaborane (2.52 g, 6.88 mmol), 2,4-difluoro-3-iodopyridine (1.66 g, 6.88 mmol), potassium carbonate (1.43 g, 10.32 mmol, 2 M aqueous solution), Pd(PPh ３ ) ４ (3 mol%) was dissolved in tetrahydrofuran (20 mL) and distilled water (according to the amount of potassium carbonate). The solution was refluxed under a nitrogen atmosphere for 12 hours and then cooled to room temperature. The solution was extracted with methylene chloride and distilled water. The organic layer was evaporated under vacuum and purified with chloroform:hexane (1:1). Compound e (2.30 g, 6.507 mmol, 94.6% yield) was obtained as a white solid. 1 H NMR (400 MH Z , CDCl3) δ8.213 (dd, J = 8.0 H Z , 5.6 H Z, 1H), 7.868 (t, J = 2.0 H Z , 1H), 7.676 (q, J = 1.6 H Z , 2H), 7.12 (dd, J = 8.0 H Z , 5.6 H Z , 1H) ASAP MS spectrum analysis: C23H5D10F2N: Calculated 353, Found 354.

[0173]

[0174] Compound f: Under a nitrogen stream, a 1 M lithium diisopropylamide solution (2.83 mL, 2.83 mmol) was added portionwise to a tetrahydrofuran solution (15 mL) of compound e (1.0 g, 2.83 mmol) and 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborane (0.53 g, 2.83 mmol) cooled to −85° C. After 10 minutes, the temperature was raised to −75° C. and the mixture was stirred for 1 hour. After the mixture was slowly returned to room temperature, 9-(4-chloro-6-(phenyl-d5)-1,3,5-triazin-2-yl)-9H-carbazole-1,2,3,4,5,6,7,8-d8 (1.15 g, 3.12 mmol), 2 M aqueous potassium carbonate solution (2.13 mL, 4.26 mmol), tetrahydrofuran (100 mL), and tetrakis(triphenylphosphine)palladium(0) (0.10 g, 0.09 mmol) were added, and the mixture was heated to reflux for 12 hours. After the reaction solution was returned to room temperature, water was added to quench the reaction, and the mixture was extracted with chloroform. The solvent was removed using an evaporator, and the mixture was purified by silica gel column chromatography (hexane:toluene=1:1) to obtain compound f (1.28 g, 1.864 mmol, yield 65.7%) as a white solid. 1 H NMR (400 MH Z , CDCl3) δ 9.4025 (d, J = 9.2 H Z , 1H), 7.953 (t, J = 1.6 H Z , 1H), 7.812 (m, 2H). ASAP MS spectrum analysis: C44H4D23F2N5: Calcd 686, Found 687.

[0175]

[0176] Compound 38317 (40) Under a nitrogen stream, a dimethylformamide solution (50 mL) of 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.77 g, 4.37 mmol), potassium carbonate (0.72 g, 5.24 mmol), and compound f (1.2 g, 1.75 mmol) was stirred overnight at 120°C. After returning the mixture to room temperature, it was quenched by adding saturated ammonium chloride solution and extracted with chloroform. The solvent was removed using an evaporator, and the residue was purified by silica gel column chromatography (toluene:hexane) to obtain compound 38317 (40) (1.70 g, 1.704 mmol, yield 97.6%). 1 H NMR (400 MH Z , CDCl3) δ 9.860 (s, 1H), 6.989 (t, J = 1.6 H Z , 1H), 6.833 (d, J= 1.6 H Z , 2H) ASAP MS Spectral Analysis: C50HD31N6: Calculated 997, Observed 998.

[0177] (Synthesis Example 4) Synthesis of Compound 46542 (1456)

[0178] Compound g: Under a nitrogen atmosphere, a 1.0 M tetrahydrofuran / hexane solution of lithium diisopropylamide (9.68 mL, 9.68 mmol) was added dropwise to a tetrahydrofuran solution (12.1 mL) of compound a (1.9 g, 9.68 mmol) at −85°C. After 1 hour, iodine (2.46 g, 9.68 mmol) dissolved in tetrahydrofuran (4.8 mL) was added dropwise, and the mixture was returned to room temperature. Then, an aqueous sodium thiosulfate solution (10 wt%) was added to quench the mixture. The mixture was then extracted with ethyl acetate and washed with saturated saline. The mixture was dried over anhydrous magnesium sulfate and filtered, and the resulting filtrate was concentrated. Compound g (1.72 g, 5.3 mmol, yield 55.1%) was obtained as a white solid by recrystallization from methylene chloride. 1 H NMR (400 MH Z , CDCl3) δ 8.43 (dd, J = 8.4 H Z,7.2, 1H) ASAP MS spectrum analysis: C11HD5F2IN: Calculated 321, Observed 323.

[0179]

[0180] Compound h: Under a nitrogen atmosphere, carbazole-1,2,3,4,5,6,7,8-d8 (1.95 g, 11.1 mmol) and potassium carbonate (1.93 g, 13.9 mmol) were added to a mixture of compound g (1.5 g, 4.65 mmol) and dimethylformamide (46 mL), and the mixture was stirred at 100°C for 15 hours. The reaction solution was cooled to room temperature, and ion-exchanged water and methanol were added, followed by filtration. The resulting solid was reprecipitated with chloroform / methanol, washed with ethyl acetate under heating, and then filtered. The resulting solid was reprecipitated with chloroform / hexane, yielding compound h (1.5 g, 2.3 mmol, yield 50.8%) as a white solid. 1 H NMR (400 MH Z , CDCl3) δ 9.26 (d, J = 6.4 H Z , 1H) ASAP MS spectrum analysis: C35HD21IN3: Calculated 632, Observed 633.

[0181]

[0182] Compound 46542 (1456) Under a nitrogen atmosphere, a 1.0 M tetrahydrofuran / hexane solution (2.6 mL, 2.6 mmol) of lithium diisopropylamide was slowly added dropwise to a tetrahydrofuran solution (9.5 mL) of compound h (1.5 g, 2.3 mmol) at -78 °C. After stirring for 30 minutes, a 1 M tetrahydrofuran solution of zinc chloride (7.1 mL, 7.1 mmol) was added, and the mixture was heated to room temperature. After stirring for 1 hour, compound I (1.54 g, 2.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.14 g, 0.11 mmol), and toluene (47 ml) were added, and the mixture was refluxed for 16 hours. The mixture was then cooled to room temperature, ion-exchanged water and methanol were added, and the resulting solid was filtered and washed with ethyl acetate, toluene, and methylene chloride to obtain a yellow solid compound 46542 (1456) (1.16 g, 1.26 mmol, yield 46%). 1H NMR (400 MH Z , CDCl3) δ 9.72 (s, 1H) ASAP MS Spectral Analysis: C62HD38N7: Calcd 919, Found 920.

[0183] (Example 1) Preparation and evaluation of thin film A thin film was prepared by vacuum deposition on a quartz substrate at a vacuum level of 1×10 －３ Compound 46542 was evaporated under conditions of less than 1×10 Pa to form a neat thin film of compound 46542 with a thickness of 100 nm. Separately, a neat thin film of compound 46542 was evaporated on a quartz substrate by vacuum evaporation under conditions of less than 1×10 Pa. －３ Compound 46542 and PyD2Cz having the following structure were evaporated from different evaporation sources under conditions of less than 1 Pa, and a doped thin film with a concentration of 20 wt% of compound 46542 was formed to a thickness of 100 nm. Instead of compound 46542, compound 46542 (40), compound 38317 (40), compound 46542 (1456), comparative compound 1, and comparative compound 2 were used, respectively, to form neat thin films and doped thin films in the same manner. Photoluminescence was analyzed when each doped thin film formed was irradiated with 300 nm excitation light, and the proportion of delayed fluorescent components and the lifetime (τ2) of the delayed fluorescent components were measured. The HOMO energy and LUMO energy were also measured using each neat thin film formed. The results are shown in the table below. As shown in the table below, it was confirmed that the compound represented by general formula (1) had a shorter delayed fluorescent lifetime (τ2) than comparative compounds 1 and 2.

[0184] (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 were laminated at 100 Pa. First, HATCN was formed on ITO to a thickness of 10 nm, NPD was formed on top of that to a thickness of 30 nm, TrisPCz was further formed on top of that to a thickness of 10 nm, and DFCz was formed on top of that to a thickness of 5 nm. Next, DFCz and compound 46542 were co-evaporated from different evaporation sources to form a 40 nm thick layer as the light-emitting layer. The concentration of compound 46542 in the light-emitting layer was 30 wt%. Next, SF3TRZ was formed to a thickness of 10 nm, and then Liq and SF3TRZ were co-evaporated from different evaporation sources to form a 30 nm thick layer. The concentrations of Liq and SF3TRZ in this layer were 30 wt% and 70 wt%, respectively. Liq was then formed to a thickness of 2 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form a cathode, resulting in an organic electroluminescence device. Instead of compound 46542, compound 46542 (40), compound 38317 (40), compound 46542 (1456), comparative compound 1, and comparative compound 2 were used to prepare organic electroluminescence devices in the same manner. Each organic electroluminescence device was driven at 2.0 mA / cm ２ The time (LT95) elapsed until the luminous intensity reached 95% of the time at the start of the test when driven at 400 rpm was measured. The results are shown in the table below. The LT95 in the table is shown as a relative value when the LT95 of Comparative Compound 2 is set as the standard (1). It was confirmed that the LT95 of each organic electroluminescence device using the compound represented by general formula (1) was long, and the device life was improved.

[0185] Example 3: Preparation and Evaluation of Organic Electroluminescence Devices Using Assist Dopants Organic electroluminescence devices were prepared using the same procedures as in Example 2, except that instead of the emitting layer in Example 2, DFCz, compound 46542, and the emitting material EM1 were vapor-deposited from different vapor deposition sources at concentrations of 69.5 wt%, 30.0 wt%, and 0.5 wt%, respectively, to form a 40 nm thick emitting layer. Furthermore, organic electroluminescence devices were prepared using the same procedures but using compound 46542 (40), compound 38317 (40), compound 46542 (1456), comparative compound 1, and comparative compound 2 instead of compound 46542. The device life was also improved when a compound represented by general formula (1) was used as an assist dopant.

[0186]

[0187] By using the compound represented by general formula (1), an organic light-emitting device having good light-emitting properties can be provided. Therefore, the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1): 【Chemical 1】 [In the general formula (1), X １ ~X ３ Each independently represents N or C(R), but X １ ~X ３ Two or three of the following are N. R represents a hydrogen atom, a deuterium atom, or a substituent. Ar １ and Ar ２ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom, １ and Ar ２ At least one of the groups is a substituted or unsubstituted heteroaryl group bonded via a nitrogen atom. L １ represents a single bond or a divalent linking group. X ４ represents C(R 1 ); X ５ represents N, and X ６ represents C(R 3 ). R １ and R3 to R ５ each independently represents a hydrogen atom, a deuterium atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a donor group. １ and R3 to R ５ At least two of R １ and R 3 to R ５ 0 to 2 of R are hydrogen atoms or deuterium atoms, １ and R3 to R ５ Only R 4 is a substituted or unsubstituted aryl group.]

2. The compound according to claim 1, wherein the donor group is a substituted or unsubstituted carbazol-9-yl group.

3. R ３ ~R ５ The compound according to claim 1 , wherein each of the groups independently represents a substituted or unsubstituted aryl group or a donor group.

4. X １ ~X ３ The compound of claim 1 , wherein is N.

5. Ar １ is a substituted or unsubstituted carbazol-9-yl group, and Ar ２ The compound according to claim 1 , wherein is a substituted or unsubstituted aryl group.

6. Ar １ and Ar ２ The compound according to claim 1, wherein each of is independently a substituted or unsubstituted carbazol-9-yl group.

7. L １ The compound of claim 1 , wherein is a single bond.

8. R １ The compound according to claim 1 , wherein is a hydrogen atom.

9. The compound of claim 1 having at least one deuterium atom.

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

11. A delayed fluorescent material comprising the compound according to any one of claims 1 to 9.

12. A film comprising the compound according to any one of claims 1 to 9.

13. An organic semiconductor device comprising the compound according to any one of claims 1 to 9.

14. An organic light-emitting device comprising the compound according to any one of claims 1 to 9.

15. The organic light-emitting device of claim 14 , comprising a layer comprising the compound, the layer also comprising a host material.

16. The organic light-emitting element according to claim 15, wherein the layer containing the compound also contains a delayed fluorescent material in addition to the compound and the host material, and the lowest excited singlet energy of the delayed fluorescent material is lower than that of the host material and higher than that of the compound.

17. The organic light-emitting device according to claim 15 , which comprises a layer containing the compound, the layer also containing a light-emitting material having a structure different from that of the compound.

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

19. 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.

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

21. The organic light-emitting device according to claim 14, which emits delayed fluorescence.

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