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

Abstract

To provide an organic light-emitting element having excellent properties.SOLUTION: An organic light-emitting element used here is a compound represented by the general formula shown below. R1-R5 each represent H, D, a cyano group, an alkyl group, an aryl group or a donating group, where at least one is a cyano group and at least two are donating groups; X1-X3 each represent N or C(R); R represents H, D or a substituent; at lease one of Ar1 and Ar2 is a group bonded through a benzene ring with a donating group connected via a nitrogen atom; L1 represents a single bond or linking group.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Research into improving the luminous efficiency of light-emitting elements such as organic electroluminescent elements (organic EL elements) has been actively conducted. In particular, various efforts have been made to improve luminous efficiency by newly developing and combining electron transport materials, hole transport materials, and luminescent materials that make up organic electroluminescent elements. Among these efforts, there has also been research into organic electroluminescent elements that use delayed fluorescent materials.

[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 that excited singlet state to the ground state. Fluorescence via this pathway is observed later than fluorescence from the excited singlet state (normal fluorescence) that arises directly from the ground state, hence the term delayed fluorescence. For example, when a light-emitting compound is excited by carrier injection, the probability of the occurrence of the excited singlet state and the excited triplet state is statistically 25%:75%, so there is a limit to the improvement in luminous efficiency when relying solely on fluorescence from the directly arisen excited singlet state. 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 pathway, resulting in higher luminous efficiency than normal 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 a benzene ring. For example, a compound has been proposed that has a skeleton in which a carbazol-9-yl group, which is a donor group, and a cyano group and a substituted triazinyl group, which are acceptor groups, are substituted on a benzene ring (see Patent Document 1). [Prior art documents] [Non-patent literature]

[0005] [Non-Patent Document 1] WO2019 / 191665A1 Summary of the Invention [Problem to be solved by the invention]

[0006] Even if a material emitting delayed fluorescence has been developed, one that has extremely good properties and no practical problems has not yet been provided. Therefore, it would be even more useful if a delayed fluorescent material with even better properties could be provided. However, the improvement of delayed fluorescent materials is still in the trial and error stage, and it is not easy to generalize the chemical structure of a useful luminescent material.

[0007] 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. [Means for solving the problem]

[0008] As a result of intensive research to achieve the above object, the present inventors have found that compounds having a structure that satisfies certain conditions are useful as light-emitting materials. The present invention has been proposed based on this finding, and specifically has the following configurations. [1] A compound represented by the following general formula (1): [ka] [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 ~R 5 At least one of R is a cyano group;1 ~R 5 At least two of X are donor groups. 1 ~X 3 Each independently represents N or C(R), but X 1 ~X 3 At least one of the groups is 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, and Ar 1 and Ar 2 At least one of L has a donor group bonded to a nitrogen atom, but is a group bonded to a benzene ring that does not have an acceptor group. 1 represents a single bond or a divalent linking group. [2] R 1 ~R 5 The compound according to [1], wherein only one of the groups is a cyano group. [3] R 2 is a cyano group. [4] Ar 1 is a group having a structure represented by the following general formula (c): [ka] In the general formula (c), each R independently represents a deuterium atom or a donor group. 6 and Ar 7 Each of Ar independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 6 and Ar 7 may be bonded to each other to form a ring structure, and Ar 6 and R may be bonded to each other to form a ring structure, and Ar 7 and R may be bonded to each other to form a cyclic structure. n represents an integer of 0 to 4. * indicates the bonding position.] [5] Ar 1 is a group having a structure represented by the following general formula (d): [ka] In the general formula (d), each R independently represents a deuterium atom or a donor group. 1 is CR 14 or N, Z 2 is CR 15 or N, Z 3 is CR 16 or N, Z 4 is CR 17 or N. Z 5 represents C or N, and 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. n represents an integer of 0 to 4. * indicates the bonding position.] [6] Ar 1 is a group having a structure represented by the following general formula (f): [ka] In the general formula (f), each R independently represents a deuterium atom or a donor group. 6 is CR 18 or N, Z 7 is CR 19 or N, Z 8 is CR 20 or N, R 18 and R 19 , R 19 and R 20 may be bonded to each other to form a ring structure. X is absent and represents a single bond, or represents a linking group having a linking chain of 1 or 2 atoms. Ar 7 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. m represents an integer of 0 to 3. * indicates the bonding position.] [7] Ar2 The compound according to any one of [1] to [6], wherein is a substituted or unsubstituted aryl group having no donor group. [8] Ar 2 is a donor group bonded via a nitrogen atom. [9] Ar 2 is a group having a structure represented by general formula (f):

[10] R 1 ~R 5 The compound according to any one of [1] to [8], wherein three of the groups are donor groups.

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

[10] , wherein the donor group is a substituted or unsubstituted carbazol-9-yl group.

[12] X 1 ~X 3 The compound according to any one of [1] to

[10] , wherein is N.

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

[12] , wherein is a single bond.

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

[13] , wherein is a hydrogen atom.

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

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

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

[15] .

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

[15] .

[18] A film containing the compound according to any one of [1] to

[15] .

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

[15] .

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

[15] .

[21] The organic light-emitting device according to

[20] , wherein the device has a layer containing the compound, the layer also containing a host material.

[22] The organic light-emitting element according to

[21] , 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.

[23] The organic light-emitting device according to

[21] or

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

[24] The organic light-emitting device according to

[21] or

[22] , wherein the compound emits the greatest amount of light among the materials contained in the device.

[25] The organic light-emitting element according to

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

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

[20] to

[25] , which is an organic electroluminescence device.

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

[20] to

[26] , which emits delayed fluorescence. [Effects of the Invention]

[0009] The compound of the present invention exhibits excellent light-emitting properties and is useful as a material for an organic light-emitting device. DETAILED DESCRIPTION OF THE INVENTION

[0010] The present invention will be described in detail below. The following description of the constituent elements may be based on typical embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits. In addition, some or all of the hydrogen atoms present in the molecules of the compound used in the present invention may be replaced with deuterium atoms ( 2In the chemical structural formulas herein, hydrogen atoms are represented by H or are omitted. For example, when the atom bonded to a carbon atom constituting the ring skeleton of a benzene ring is omitted, it is assumed that H is bonded to the carbon atom constituting the ring skeleton at the omitted position. In this specification, the term "substituent" refers to an atom or atomic group other than a hydrogen atom or a deuterium atom. On the other hand, the term "substituted or unsubstituted" means that a hydrogen atom may be substituted with a deuterium atom or a substituent.

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

[0012] 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 ~R 5 At least one of R is a cyano group; 1 ~R 5 At least two of X are donor groups. 1 ~X 3 Each independently represents N or C(R), but X 1 ~X 3 At least one of the groups is 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, and Ar 1 and Ar 2At least one of the groups has a donor group bonded via a nitrogen atom, but is a group bonded via a benzene ring that does not have an acceptor group. Here, "having a donor group bonded via a nitrogen atom" means that the nitrogen atom constituting the donor group is directly bonded to the benzene ring. Also, "not having an acceptor group" means that the acceptor group is not directly bonded to the benzene ring.

[0013] R 1 ~R 5 The alkyl group may be linear, branched, or cyclic. It may also be a mixture of two or more of the linear, cyclic, and branched moieties. The number of carbon atoms in the alkyl group may be, for example, 1 or more, 2 or more, or 4 or more. It may also 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.

[0014] 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 from, for example, 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 aspect of the invention, the aryl group is unsubstituted. In the following, R 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. [ka] JPEG2024123555000007.jpg206167JPEG2024123555000008.jpg148164

[0015] In addition to the above specific examples, groups in which all hydrogen atoms present in Ar1 to Ar44 are substituted with deuterium atoms are exemplified here as Ar45 to Ar88, in this order. In one aspect of the present invention, R 1 ~R 5The aryl group that R can take is selected from the group consisting of Ar1 to Ar88. 1 ~R 5 The aryl group that R can take is Ar1 or Ar45. In one embodiment of the present invention, R 1 ~R 5 The aryl group that R can take is selected from the group consisting of Ar2 to Ar11, Ar26 to Ar35, Ar46 to Ar55, and Ar70 to Ar79. 1 ~R 5 The aryl group that R can take is selected from the group consisting of Ar12 to Ar19, Ar36 to Ar43, Ar56 to Ar63, and Ar80 to Ar87. 1 ~R 5 The aryl group that R can take is selected from the group consisting of Ar21 to Ar26 and Ar65 to Ar70. 1 ~R 5 The aryl group that can be taken by Ar is selected from the group consisting of Ar1, Ar12 to Ar14, Ar23, Ar36 to Ar38, Ar45, Ar56 to Ar58, Ar67, and Ar80 to Ar82. In one aspect of the present invention, Ar 1 or Ar 2 The aryl group that can be taken by is selected from the group consisting of Ar1 to Ar88. In one embodiment of the present invention, Ar 1 or Ar 2 The aryl group that can be taken by Ar is Ar or Ar. In one embodiment of the present invention, Ar 1 or Ar 2 The aryl group that can be taken by Ar is selected from the group consisting of Ar2 to Ar11, Ar26 to Ar35, Ar46 to Ar55, and Ar70 to Ar79. 1 or Ar 2 The aryl group that R can take is selected from the group consisting of Ar12 to Ar19, Ar36 to Ar43, Ar56 to Ar63, and Ar80 to Ar87. 1 ~R 5 The aryl group which can be taken by is selected from the group consisting of Ar1, Ar12 to Ar14, Ar36 to Ar38, Ar45, Ar56 to Ar58, and Ar80 to Ar82.

[0016] R in general formula (1) 1 ~R 5 At least two of R are donor groups. 1 ~R 5 The donor groups that can be taken by the formula (1) do not include substituted or unsubstituted aryl groups. The "donor group" can be selected from groups with a negative Hammett σp value. The "acceptor group" can be selected from groups with a positive Hammett σp value. The Hammett σp value was proposed by L.P. Hammett, and quantifies the effect of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, the following equation holds between the substituent in a para-substituted benzene derivative and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp or log(K / K0) = ρσp where k is the rate constant for a benzene derivative having no substituent, k is the rate constant for a benzene derivative substituted with a substituent, K is the equilibrium constant for a benzene derivative having no substituent, K is the equilibrium constant for a 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, please refer to the description of the σp value in Hansch, C. et al., Chem. Rev., 91, 165-195 (1991).

[0017] 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, and may be selected, for example, from the range of −0.9 or less, or from the range of −1.1 or less.

[0018] 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.The two aryl groups constituting the diarylamino group here may be bonded to each other, and the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other.

[0019] R 1 ~R 5 The donor group that can be taken by is preferably a group represented by the following general formula (a). [ka]

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

[0021] Z 1 ~Z 4 Among these, the number of N is preferably 0 to 3, and more preferably 0 to 2. In one embodiment of the present invention, Z 1 ~Z 4 In one embodiment of the present invention, the number of N is 1. 1 ~Z 4 The number of N is 0. R 14 ~R 17 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). R 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 the indole, and examples of the substituent include a substituent selected from any of Substituent Groups A to E. The cyclic structure may be a substituted or unsubstituted cyclopentadiene ring. In one aspect of the present invention, R 14 and R 15 , R 15 and R 16 , R 16 and R 17 In one embodiment of the present invention, a pair of R 14 and R 15 , R 15 and R 16 , R 16 and R 17 are not bonded to each other to form a ring structure.

[0022] In the general formula (a), Z 5 represents C or N, and 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. Ar 5 An example of the aromatic ring that can be used is a benzene ring. The benzene ring may be 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 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, the heteroaromatic ring can be 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. In one embodiment of the present invention, 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, 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.

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

[0024] In the general formula (b), Z 1 is CR 14 or N, Z 2 is CR 15 or N, Z 3 is CR 16 or N, Z 4 is CR 17 or N, Z 6 is CR 18 or N, Z 7 is CR 19 or N, Z 8 is CR 20 or N, Z 9 is CR 21 or N. R 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. Z in general formula (b) 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 to Z in general formula (a) in order. 1 ~Z 4 , R 14 ~R 17You can refer to the explanation in In one aspect of the present invention, Z 1 ~Z 4 , Z 6 ~Z 9 Among these, the number of N is preferably 0 to 2, and more preferably 0 or 1. In one embodiment of the present invention, Z 1 ~Z 4 , Z 6 ~Z 9 In a preferred embodiment of the present invention, the number of N groups is 1. 1 ~Z 4 , Z 6 ~Z 9 The number of N groups is 0. When it is 0, it represents a substituted or unsubstituted carbazol-9-yl group.

[0025] 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. In addition, one or more rings may be further fused to the two benzene rings constituting the carbazol-9-yl group. In one preferred embodiment of the present invention, R 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.

[0026] In one aspect of the present invention, R 1 ~R 5The 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 5 The ring-fused carbazol-9-yl group represented by the formula (I) may be unsubstituted, 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 optionally substituted with one atom or group, or a combination of two or more groups, selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group.

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

[0028] The ring-fused carbazole-9-yl group is a group bonded via a nitrogen atom constituting the ring skeleton of carbazole, and has a structure in which a ring is fused to at least one of the two benzene rings constituting carbazole. The fused ring may be any of an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, and 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 used. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring may be used 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 only a deuterium atom is present), and more preferably to an aryl group optionally substituted with an alkyl group or an aryl group. In the present invention, a carbazol-9-yl group fused to a ring having one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom as ring skeleton-constituting atoms is preferably used. Among 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 used. 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 fused with a benzothieno structure, for example, two or more carbazol-9-yl groups.

[0029] 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 used. Furthermore, examples of the ring-fused carbazole-9-yl group include an indolo[2,3-a]carbazole-9-yl group, an indolo[3,2-a]carbazole-9-yl group, an indolo[2,3-b]carbazole-9-yl group, an indolo[3,2-b]carbazole-9-yl group, an indolo[2,3-c]carbazole-9-yl group, and an indolo[3,2-c]carbazole-9-yl group.

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

[0031] 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 (C6H5), and * indicates the bonding position. Methyl groups are not shown, so for example, D2 has one methyl group. However, a deuterated methyl group is represented as CD3. Furthermore, C6D5 represents a phenyl group in which all hydrogen atoms are deuterated. D represents a deuterium atom. [ka] JPEG2024123555000012.jpg246170JPEG2024123555000013.jpg253169JPEG2024123555000014.jpg240170JPEG2024123555000015.jpg212170JPEG202 4123555000016.jpg216170JPEG2024123555000017.jpg219170JPEG2024123 555000018.jpg209170JPEG2024123555000019.jpg212170JPEG20241235550 00020.jpg210170JPEG2024123555000021.jpg213170JPEG2024123555000022.jpg243170JPEG2024123555000023.jpg228170JPEG2024123555000024.j pg230163JPEG2024123555000025.jpg248170JPEG2024123555000026.jpg240163JPEG2024123555000027.jpg237163JPEG2024123555000028.jpg250170 JPEG2024123555000029.jpg228170JPEG2024123555000030.jpg238162JPEG2024123555000031.jpg224170JPE G2024123555000032.jpg210170JPEG2024123555000033.jpg250165JPEG2024123555000034.jpg220170JPEG202 4123555000035.jpg220170JPEG2024123555000036.jpg248163JPEG2024123555000037.jpg212170JPEG2024123 555000038.jpg213170JPEG2024123555000039.jpg236170JPEG2024123555000040.jpg237170JPEG20241235550 00041.jpg229170JPEG2024123555000042.jpg220170JPEG2024123555000043.jpg245170JPEG20241235550000 44.jpg230167JPEG2024123555000045.jpg252170JPEG2024123555000046.jpg223170JPEG2024123555000047.j pg228170JPEG2024123555000048.jpg242170JPEG2024123555000049.jpg214170JPEG2024123555000050.jpg24 2170JPEG2024123555000051.jpg227170JPEG2024123555000052.jpg255170JPEG2024123555000053.jpg213170

[0032] All hydrogen atoms present in the above D1 to D464 are substituted with deuterium atoms and are disclosed as D727 to D1190. In one aspect of the present invention, R 1 ~R 5 The donor group that can be taken by R is selected from the group consisting of D1 to D1190. 1 ~R 5The donor group that can be taken by R is selected from the group consisting of D1 to D16 and D465 to D476. 1 ~R 5 The donor group that R can take is selected from the group consisting of D17 to D76, D88 to D123, D190 to D303, D364 to D458, D477 to D524, D531 to D658, and D709 to D715. 1 ~R 5 The donor group that can be taken by the formula (I) is selected from the group consisting of D77 to D82, D124 to D189, D304 to D363, D460 to D464, D525 to D530, D659 to D708, and D717 to D726. In one aspect of the present invention, R 1 ~R 5 The donor group that R can take is selected from the group consisting of D1 to D189, D458 to D654, and D717 to D726. 1 ~R 5 The donor group that R can take is selected from the group consisting of D1 to D22, D35 to D38, D46 to D53, D74 to D89, D117 to D187, D458, D459, D465 to D478, D526 to D533, and D717 to D721. 1 ~R 5 The donor group that can be taken by R is selected from the group consisting of D1 to D13, D17 to D22, D37, D47 to D52, D77 to D82, D124 to D136, D139, D142, D145, D151, D154, D157, D160, D163, D166, D169, D172, D175, D178, D181, D184, D187, D459, D466 to D471, D521 to D525, and D712 to D716. For example, in a more preferred embodiment of the present invention, R 1 ~R 5 The donor group that can be taken by R is selected from the group consisting of D1 to D13 and D466 to D471. 1 ~R 5 The donor group that can be taken by R is selected from the group consisting of D17 to D22, D37, and D47 to D52. 1 ~R5 The donor group that can be taken by R is selected from the group consisting of D77 to D82 and D526 to D530. For example, in a more preferred embodiment of the present invention, 1 ~R 5 The donor group that can be taken by is selected from the group consisting of D124 to D136, D139, D142, D145, D151, D154, D157, D160, D163, D166, D169, D172, D175, D178, D181, D184, D187, and D712 to D716.

[0033] R in general formula (1) 1 ~R 5 In one embodiment of the present invention, one or more of R 1 ~R 5 In a preferred embodiment of the present invention, one or two of R 2 is a cyano group. In one embodiment of the present invention, at least R 1 is a cyano group. In one embodiment of the present invention, at least R 3 is a cyano group. In a preferred embodiment of the present invention, R 2 In one aspect of the invention, only R 1 In one aspect of the invention, only R 3 In one aspect of the invention, only R 2 and R 4 In one aspect of the invention, only R 2 and R 5 In one aspect of the invention, only R 1 and R 3 is the only cyano group.

[0034] R in general formula (1) 1 ~R 5 In one embodiment of the present invention, two or more of R 1 ~R 5 In a preferred embodiment of the present invention, two or three of R 1 ~R 5 In a preferred embodiment of the present invention, two of R 1 ~R 5In one embodiment of the present invention, at least three of 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 3 In one embodiment of the present invention, R 4 In one embodiment of the present invention, R 5 In one embodiment of the present invention, R 3 and R 5 In one embodiment of the present invention, R 2 and R 5 In one embodiment of the present invention, R 2 and R 4 In one embodiment of the present invention, R 3 and R 4 and R 5 In one embodiment of the present invention, R 2 and R 4 and R 5 Only R is a donor group. 1 ~R 5 When two or more of the groups are donor groups, they may be the same or different. R 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. For example, R 1 is a hydrogen atom or a deuterium atom. 1 ~R 5 R has better luminescence properties than compounds in which the number of hydrogen atoms or deuterium atoms is three. 1 ~R 5 The number of substituted or unsubstituted aryl groups among R is 0 or 1, and preferably 1. 1 ~R 5 Among these, the number of substituted or unsubstituted alkyl groups is 0 to 3, preferably 0 to 2, and may be 1 or 0.

[0035] In a preferred embodiment of the present invention, R 1 ~R 5 One of R is a cyano group, two 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, R 1 is a hydrogen atom or a deuterium atom, and R 2 or R 3 is a cyano group. In a preferred embodiment of the present invention, R 1 is a hydrogen atom or a deuterium atom, and R 2 is a cyano group, and R 3 and R 5 is a donor group, and R 4 is a substituted or unsubstituted aryl group. 1 is a hydrogen atom or a deuterium atom, and R 2 is a cyano group, and R 4 and R 5 is a donor group, and R 3 is a substituted or unsubstituted aryl group. 1 is a hydrogen atom or a deuterium atom, and R 2 is a cyano group, and R 3 and R 4 is a donor group, and R 5 is a substituted or unsubstituted aryl group. In a preferred embodiment of the present invention, R 1 ~R 5 One of R is a cyano group, three 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, R 1 is a hydrogen atom or a deuterium atom, and R 2 is a cyano group, and R 3 ~R 5 is a donor group. In one embodiment of the present invention, R 1 is a hydrogen atom or a deuterium atom, and R3 is a cyano group, and R 2 , R 4 and R 5 is a donor group. In one aspect of the present invention, R 1 ~R 5 In one embodiment of the present invention, one of R is a cyano group, two are donor groups, and two are hydrogen atoms or deuterium atoms. 1 and R 4 is a hydrogen atom or a deuterium atom, and R 2 is a cyano group, and R 3 and R 5 is a donor group. In one aspect of the invention, R 1 and R 5 is a hydrogen atom or a deuterium atom, and R 2 is a cyano group, and R 3 and R 4 is a donor group. In one aspect of the invention, R 1 and R 3 is a hydrogen atom or a deuterium atom, and R 2 is a cyano group, and R 4 and R 5 is a donor group. In one aspect of the invention, R 1 and R 4 is a hydrogen atom or a deuterium atom, and R 3 is a cyano group, and R 2 and R 5 is the donor group.

[0036] Ar in general formula (1) 1 and Ar 2 Regarding the aryl groups that can be taken by R 1 ~R 5 The explanation and preferred range of aryl groups that can be taken by the formula (I) can be referred to. Ar in general formula (1) 1 and Ar 2The heteroaryl group may be a single ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4. Specific examples of the ring include a 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 from the range of 5 to 16, or may be selected from the range of 5 to 12. Ar in general formula (1) 1 and Ar 2 At least one of the groups has a donor group bonded to a nitrogen atom, but is a group bonded to a benzene ring that is not substituted with an acceptor group (hereinafter referred to as a "donor group bonded to a carbon atom"). 1 and Ar 2 At least one of the groups is a group bonded to a carbon atom constituting the ring skeleton of a benzene ring, and the benzene ring has a donor group bonded to it via a nitrogen atom but no acceptor group bonded to it. The benzene ring may further have a hydrogen atom, a deuterium atom, or a donor group not bonded to it via a nitrogen atom bonded to it. The donor group bonded via a carbon atom preferably has a structure represented by the following general formula (c). [ka]

[0037] In the general formula (c), Ar 6 and Ar 7Each of the groups independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. The heteroaryl group preferably contains a nitrogen atom as a ring skeleton-constituting atom, and an example of such a heteroaryl group is a pyridine ring-containing heteroaryl group. For details of aryl groups and heteroaryl groups, see Ar 1 and Ar 2 The description of the aryl and heteroaryl groups that Ar can take can be found in the following. 6 and Ar 7 is preferably a substituted or unsubstituted aryl group, for example, a substituted or unsubstituted phenyl group. Each R independently represents a deuterium atom or a donor group. The donor group that can be taken by R may be a donor group bonded via a nitrogen atom, or may be a donor group bonded via an atom other than a nitrogen atom (for example, a carbon atom). A donor group bonded via a nitrogen atom is N(Ar 6 )(Ar 7 ) may be the same as or different from Ar 6 and Ar 7 may be bonded to each other to form a ring structure, and Ar 6 and R may be bonded to each other to form a ring structure, and Ar 7 and R may be bonded to each other to form a cyclic structure. 6 and Ar 7 are bonded to each other to form a ring structure. In another preferred embodiment of the present invention, Ar 6 and R are bonded to each other to form a cyclic structure. When they are bonded to each other, they are bonded via a single bond or a linking group. They are preferably bonded via a single bond or a nitrogen atom (the nitrogen atom is preferably bonded to an alkyl group or an aryl group), and more preferably bonded via a single bond. n represents an integer of 0 to 4. * indicates the bonding position.

[0038] In a preferred embodiment of the present invention, the donor group bonded via a carbon atom has a structure represented by the following general formula (d), and more preferably has a structure represented by the following general formula (e). [ka]

[0039] Z in general formula (d) 1 ~Z 5 , Ar 5 For the definition and explanation of Z in general formula (e), reference can be made to the corresponding description in general formula (a). 1 ~Z 4 , Z 6 ~Z 9 For the definition and explanation of, please refer to the corresponding description of general formula (b). In general formula (d) and general formula (e), R each independently represents a deuterium atom or a donor group. The donor group that R can take may be a donor group bonded via a nitrogen atom, or may be a donor group bonded via an atom other than a nitrogen atom (for example, a carbon atom). n represents an integer of 0 to 4. * indicates the bonding position. It is preferred that n is 0 or n is 4 and all four R's are deuterium atoms. 1 ~Z 4 , Z 6 ~Z 9 Among these, preferably 0 to 2, preferably 0 to 1, and more preferably 0 are nitrogen atoms. As specific examples of groups represented by general formula (d) or (e), phenyl groups in which the above D1 to D1190 are bonded to the 3-position (i.e., groups in which a metaphenylene group is further bonded to the * of D1 to D1190) are disclosed as D1191 to D2380. Phenyl groups in which the above D1 to D1190 are bonded to the 4-position (i.e., groups in which a paraphenylene group is further bonded to the * of D1 to D1190) are disclosed as D2381 to D3570. Perdeuterated phenyl groups in which the above D1 to D1190 are bonded to the 3-position (i.e., groups in which a metaphenylene group in which all hydrogen atoms are deuterated is further bonded to the * of D1 to D1190) are disclosed as D3571 to D4760. Perdeuterated phenyl groups in which the above D1 to D1190 are bonded to the 4-position (that is, groups in which a paraphenylene group in which all hydrogen atoms are deuterated is further bonded to * in D1 to D1190) are disclosed as D4761 to D5950.

[0040] In a preferred embodiment of the present invention, the donor group bonded via a carbon atom has a structure represented by the following general formula (f). [ka]

[0041] Z in general formula (f) 6 ~Z 8 For the definition and explanation of Ar in general formula (f), reference can be made to the corresponding description in general formula (a). 7 For the definition and explanation of X, please refer to the corresponding description of general formula (c). X is absent and represents a single bond, or represents a linking group having a linking chain of 1 or 2 atoms. Examples of linking groups having a linking chain of 2 atoms include substituted or unsubstituted ethylene groups. Examples of linking groups having a linking chain of 1 atom include oxygen atoms, sulfur atoms, and nitrogen atoms bonded to aryl groups or alkyl groups. The linking group is preferably a nitrogen atom bonded to an aryl group or alkyl group. More preferably, X is absent and represents a single bond. R represents a deuterium atom or a donor group. The donor group that R can take may be a donor group bonded via a nitrogen atom, or may be a donor group bonded via an atom other than a nitrogen atom (for example, a carbon atom). m represents an integer of 0 to 3. * indicates the bonding position. It is preferred that m is 0 or m is 3 and all three R's are deuterium atoms. 6 ~Z 8 In a preferred embodiment of the present invention, X is a single bond, and Z 6 ~Z 8 of which 0 is a nitrogen atom. In one embodiment of the present invention, it is a substituted or unsubstituted N-arylcarbazol-1-yl group. In one embodiment of the present invention, it is a substituted or unsubstituted N-arylcarbazol-2-yl group. In a preferred embodiment of the present invention, it is a substituted or unsubstituted N-arylcarbazol-3-yl group. In one embodiment of the present invention, it is a substituted or unsubstituted N-arylcarbazol-4-yl group.

[0042] Specific examples of donor groups represented by general formula (f) are shown below. However, the donor groups that can be employed in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, Ph represents a phenyl group (C6H5), and * represents the bonding position. Methyl groups are not shown, so for example, Z2 has one methyl group. However, a deuterated methyl group is represented as CD3. Furthermore, C6D5 represents a phenyl group in which all hydrogen atoms are deuterated. D represents a deuterium atom.

[0043] [ka] JPEG2024123555000058.jpg219170JPEG2024123555000059.jpg188170JPEG2024123555000060.jpg220170JPEG2024123555000061.jpg195170 JPEG2024123555000062.jpg211170JPEG2024123555000063.jpg243170JPEG2024123555000064.jpg239170JPEG2024123555000065.jpg178170

[0044] Z157 to Z312 are compounds in which all hydrogen atoms present in Z1 to Z156 have been replaced with deuterium atoms. Z313 to Z468 are compounds in which hydrogen atoms bonded to the phenyl group and alkyl group (methyl group and tert-butyl group) present in Z1 to Z156 have been replaced with deuterium atoms.

[0045] In one aspect of the present invention, Ar 1 and Ar 2The donor group bonded through a carbon atom is selected from the group consisting of Z1 to Z468. In one embodiment of the present invention, the donor group bonded through a carbon atom is selected from the group consisting of Z1 to Z8, Z89 to Z96, Z157 to Z164, Z245 to Z252, Z313 to Z320, and Z401 to Z408. In one embodiment of the present invention, the donor group bonded through a carbon atom is selected from the group consisting of Z9 to Z88, Z97 to Z156, Z165 to Z244, Z253 to Z312, Z321 to Z400, and Z409 to Z468. In one embodiment of the present invention, the donor group bonded through a carbon atom is selected from the group consisting of Z1 to 88, Z157 to Z244, and Z313 to Z400. In one embodiment of the present invention, the donor group bonded via a carbon atom is selected from the group consisting of Z89 to Z156, Z245 to Z312, and Z401 to Z468.

[0046] In one aspect of the present invention, Ar 1 and Ar 2 The donor group bonded at the carbon atom which can be selected from the group consisting of D1191 to D5950. 1 and Ar 2 The donor group bonded at the carbon atom which can be selected from the group consisting of D1191 to D2380 and D3571 to D4760. 1 and Ar 2 The donor group bonded at the carbon atom which can be selected from the group consisting of D2381 to D3570 and D4761 to D5950. In one embodiment of the present invention, the donor group bonded at a carbon atom is selected from the group consisting of D1191 to D1206, D1655 to D1666, D3571 to D3586, and D4035 to D4046. In one embodiment of the present invention, the donor group bonded at a carbon atom is selected from the group consisting of D2381 to D2396, D2845 to D2856, D4761 to D4776, and D5225 to D5236. In one embodiment of the present invention, the donor group bonded at a carbon atom is selected from the group consisting of D1207 to D1266, D1278 to D1313, D1380 to D1493, D1554 to D1648, D1667 to D1714, D1721 to D1848, D1899 to D1905, D3587 to D3646, D3658 to D3693, D3760 to D3873, D3934 to D4028, D4047 to D4094, D4101 to D4228, and D4279 to D4285. In one embodiment of the present invention, the donor group bonded at a carbon atom is selected from the group consisting of D2397 to D2456, D2468 to D2503, D2570 to D2683, D2744 to D2838, D2857 to D2904, D2911 to D3038, D3089 to D3095, D4777 to D4836, D4848 to D4883, D4950 to D5063, D5124 to D5218, D5237 to D5284, D5291 to D5418, and D5469 to D5475. In one embodiment of the present invention, the donor group bonded via a carbon atom is selected from the group consisting of D1267 to D1272, D1314 to D1379, D1494 to D1553, D1650 to D1654, D1715 to D1720, D1849 to D1989, D1907 to D1916, D3647 to D3652, D3694 to D3759, D3874 to D3933, D4030 to D4034, D4095 to D4100, 4229 to D4278, and D4287 to D4296. In one embodiment of the present invention, the donor group bonded via a carbon atom is selected from the group consisting of D2457 to D2462, D2504 to D2569, D2684 to D2743, D2840 to D2844, D2905 to D2910, D3039 to D3088, D3097 to D3106, D4837 to D4842, D4884 to D4949, D5064 to D5123, D5220 to D5224, D5285 to D5290, D5419 to D5468, and D5477 to D5486.In one embodiment of the present invention, the donor group bonded at a carbon atom is selected from the group consisting of D1191 to D1379, D1648 to D1844, D1907 to D1916, D3571 to D3759, D4028 to D4224, and D4287 to D4296. In one embodiment of the present invention, the donor group bonded at a carbon atom is selected from the group consisting of D2381 to D2659, D2838 to D3034, D3097 to D3106, D4761 to D4949, D5218 to D5414, and D5477 to D5486.

[0047] In one aspect of the present invention, Ar 1 and Ar 2 Among them, Ar 1 In one embodiment of the present invention, the Ar 1 and Ar 2 In one embodiment of the present invention, both of Ar in general formula (1) are the same donor group bonded at a carbon atom. 1 and Ar 2 In a preferred embodiment of the present invention, Ar in general formula (1) is a donor group having the same structure but different from Ar in general formula (1). 1 is a donor group bonded at a carbon atom, and Ar 2 is a substituted or unsubstituted aryl group (for example, any of Ar1 to Ar88), or a donor group bonded via a nitrogen atom (for example, any of D1 to D1190). The substituted or unsubstituted aryl group here and its preferred range are described in R 1 ~R 5 , Ar 1 , Ar 2 For the description of the donor group and its preferred range, please refer to the corresponding description of the substituted or unsubstituted aryl group that can be taken by R in general formula (1). 1 ~R 5 Reference can be made to the corresponding descriptions of the donor groups that can be taken by the formula (I).

[0048] L in general formula (1) 1represents 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 Refer to the description and preferred range of the aryl group in the section describing the heteroarylene group. Examples of the heteroarylene group include a linking group in which at least one of the ring skeletal carbon atoms constituting the arylene group is substituted with a nitrogen atom. In the following, L 1 However, the L that can be used in the present invention is 1 However, these specific examples should not be construed as limiting. In the following specific examples, methyl groups are omitted. Therefore, for example, L3 to L5 are substituted with methyl groups. * indicates a bonding position. L1 is a single bond.

[0049] [ka]

[0050] All hydrogen atoms in L2 to L13 are replaced with deuterium atoms, and L14 to L25 are disclosed. 1 is selected from the group consisting of L1 to L25. In one embodiment of the present invention, L 1 is selected from the group consisting of L1 to L7 and L14 to L19. 1 is selected from the group consisting of L1, L8 to L13, and L20 to L25. 1 is selected from the group consisting of L2 to L25.

[0051] X in general formula (1) 1 ~X 3Each 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, X 1 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.

[0052] In a preferred embodiment of the present invention, X 1 ~X 3 is N and L 1 is a single bond, and Ar 1 is a group represented by general formula (d), and Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group not having a donor group, for example, a group represented by general formula (d)), or a donor group bonded via a nitrogen atom, and R 2 is a cyano group, and R 1 , R 3 ~R 5two 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. In a preferred embodiment of the present invention, X 1 ~X 3 is N and L 1 is a single bond, and Ar 1 is a group represented by general formula (e), and Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group not having a donor group, for example, a group represented by general formula (d)), or a donor group bonded via a nitrogen atom, and R 2 is a cyano 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. In a preferred embodiment of the present invention, X 1 ~X 3 is N and L 1 is a single bond, and Ar 1 is a group represented by general formula (d), and Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group not having a donor group, for example, a group represented by general formula (d)), or a donor group bonded via a nitrogen atom, and R 2 is a cyano 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. In a preferred embodiment of the present invention, X 1 ~X 3 is N and L 1 is a single bond, and Ar 1 is a group represented by general formula (e), and Ar 2is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group not having a donor group, for example, a group represented by general formula (d)), or a donor group bonded via a nitrogen atom, and R 2 is a cyano 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. In a preferred embodiment of the present invention, X 1 ~X 3 is N and L 1 is a single bond, and Ar 1 is a group represented by general formula (d), and Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group not having a donor group, for example, a group represented by general formula (d)), or a donor group bonded via a nitrogen atom, and R 3 is a cyano group, and R 1 , R 2 , R 4 , R 5 Among them, 2 to 3 are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), and 1 to 2 (preferably at least R 1 ) is a hydrogen atom or a deuterium atom, and 0 to 1 is a substituted or unsubstituted aryl group. In a preferred embodiment of the present invention, X 1 ~X 3 is N and L 1 is a single bond, and Ar 1 is a group represented by general formula (e), and Ar 2 is a substituted or unsubstituted aryl group (for example, a substituted or unsubstituted aryl group not having a donor group, for example, a group represented by general formula (d)), or a donor group bonded via a nitrogen atom, and R 3 is a cyano group, and R 1 , R 2 , R 4 , R 5Among them, 2 to 3 are donor groups (preferably substituted or unsubstituted carbazol-9-yl groups), and 1 to 2 (preferably at least R 1 ) is a hydrogen atom or a deuterium atom, and 0 to 1 is a substituted or unsubstituted aryl group. In each of the above preferred embodiments, Ar 2 is, for example, a substituted or unsubstituted aryl group having no donor group. 2 is a donor group bonded via, for example, a nitrogen atom. 2 is, for example, a group represented by general formula (e). 2 is, for example, a group represented by general formula (f).

[0053] 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. The compound represented by general formula (1) may also 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 also 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 also 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 not contain hydrogen atoms, but may contain deuterium atoms.

[0054] In the present specification, the term "substituent group A" refers to a deuterium atom, a hydroxyl group, a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (for example, having 1 to 40 carbon atoms), an alkoxy group (for example, having 1 to 40 carbon atoms), an alkylthio group (for example, having 1 to 40 carbon atoms), an aryl group (for example, having 6 to 30 carbon atoms), an aryloxy group (for example, having 6 to 30 carbon atoms), an arylthio group (for example, having 6 to 30 carbon atoms), a heteroaryl group (for example, having 5 to 30 ring skeleton atoms), a heteroaryloxy group (for example, having 5 to 30 ring skeleton atoms), It means one atom or group, or a combination of two or more selected from the group consisting of heteroarylthio groups (for example, having 5 to 30 atoms constituting the ring skeleton), acyl groups (for example, having 1 to 40 carbon atoms), alkenyl groups (for example, having 1 to 40 carbon atoms), alkynyl groups (for example, having 1 to 40 carbon atoms), alkoxycarbonyl groups (for example, having 1 to 40 carbon atoms), aryloxycarbonyl groups (for example, having 1 to 40 carbon atoms), heteroaryloxycarbonyl groups (for example, having 1 to 40 carbon atoms), silyl groups (for example, trialkylsilyl groups having 1 to 40 carbon atoms), and nitro groups. In this specification, the term "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 skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), and a diarylaminoamino group (e.g., having 0 to 20 carbon atoms). In this specification, the term "substituent group C" 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), a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms). In this specification, the term "substituent group D" 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), and a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms). As used herein, the term "substituent group E" 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), and an aryl group (e.g., having 6 to 22 carbon atoms). In the present specification, when it is described as "substituted or unsubstituted" or "optionally substituted", the substituent may be selected from, for example, Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E.

[0055] Specific examples of the compound represented by general formula (1) are shown in the following Tables 1 to 4. 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 in the following general formula (1a) 3 ~R 5 The structure of each compound is shown individually by specifying each compound. 1 is a 4-(perdeuterated carbazol-9-yl)phenyl group (D3107), and Ar 2 is a perdeuterated phenyl group (Ar45), and X 1 ~X 3 is a nitrogen atom (N), and L 1 is a single bond (L1), and R 1 is a hydrogen atom, and R 2 is a cyano group, and R 3 ~R 5 The structures in which is a group specified in Table 1 are individually shown as the structures of compounds 1 to 240. [ka] [Table 1]

[0056] In Table 2, each row contains the R 3 ~R 5 By displaying these together, the structures of compounds 1 to 1594600 are shown. For example, in the column of compounds 1 to 240 in Table 2, R 3 ~R 5 The compounds having the same value and D1 to D240 are designated as compounds 1 to 240 in order. That is, the column of compounds 1 to 240 in Table 2 shows all the compounds 1 to 240 specified in Table 1 in one column. Similarly, in the column of compounds 241 to 5950 in Table 2, R 3 ~R 5 The compounds D241 to D5950 are designated as compounds 241 to 5950 in order. 4 is fixed to H (hydrogen atom), and R 3 and R 5 The compounds D1 to D5950, which are the same in value, are designated as compounds 5951 to 11900, respectively. 4 is fixed to Ar1, and R 3 and R 5 Compounds D1 to D5950 that are the same are designated as compounds 11901 to 17850. Compounds 17851 to 1594600 in Table 2 are also identified in the same manner. [Table 2] JPEG2024123555000070.jpg255139JPEG2024123555000071.jpg255147JPEG2024123555000072.jpg255150JPEG2024123555000073.jpg135157

[0057] 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. [ka] [Table 3] JPEG2024123555000076.jpg255147JPEG2024123555000077.jpg255151JPEG2024123555000078.jpg255150JPEG2024123555000079.jpg136157

[0058] In Tables 1 to 3, Ar in general formula (1) 1 is a 4-(perdeuterated carbazol-9-yl)phenyl group (D3107), and Ar 2 The structures of compounds 1 to 3189200 were identified as those in which Ar is a perdeuterated phenyl group (Ar45). Table 4 shows the structure of each of compounds 1 to 3189200. 1 and Ar 2 The compounds in which the Ar of Compound 1 is changed as shown in Table 4 are listed in order in a table format. In Table 4, in order to make the correspondence easier to understand, Compounds 1 to 3189200 are also listed in the first row. In the second row of Table 4, for example, Compound 1(1) is the Ar of Compound 1. 1 Compound 2(1) shows a compound having a structure in which Ar of Compound 2 is substituted with D1191. 1 Compound 3189200(1) shows the compound having the structure in which Ar of compound 3189200 is substituted with D1191. 1 The compounds having a structure in which D1191 is substituted with D1191 are shown. Compounds 1(2) to 3189200(2) in the third row of Table 4 and the compounds in subsequent rows are also identified in the same manner. 1 ~X 3 are both nitrogen atoms (N), and L 1 is a single bond (L1), and R 1 is a hydrogen atom. [Table 4] JPEG2024123555000081.jpg255156JPEG2024123555000082.jpg98158

[0059] Compounds 1-3, 189200 Ar 1 and Ar 2 The compounds in which both are D1191 are designated as compounds 1(1191) to 3189200(1191), respectively. 1 and Ar 2 The compounds in which both are D1192 are designated as compounds 1(1192) to 3189200(1192) in this order. 1 and Ar 2 The compounds in which both are Dx (x = 1191 to 5950) are called compounds 1(x) to 3189200(x). Finally, the Ar 1 and Ar 2 The compounds in which both are D5950 are compounds 1(5950) to 3189200(5950), in that order. Compounds 1-3, 189200 Ar 1 and Ar 2 The compounds in which both are Z1 are designated as compounds 1(Z1) to 3189200(Z1), respectively. 1 and Ar 2 The compounds in which both are Z2 are designated as compounds 1(Z2) to 3189200(Z2), respectively. 1 and Ar 2 The compounds where both are Zx (x = 1 to 468) are called compounds 1(x) to 3189200(x). Finally, the Ar 1 and Ar 2 The compounds in which both are Z468 are compounds 1(Z468) to 3189200(Z468), in that order. 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. In one embodiment of the present invention, the compounds are selected from the group consisting of compounds 1 to 3189200 and compounds 1(n) to 3189200(n) [where n is 1 to 255, 1191 to 5950, Z1 to Z468].

[0060] When it is intended to use an organic layer containing the compound represented by general formula (1) formed by vapor deposition, 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. 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 the coating method, it is possible to form a film even from a compound with a relatively large molecular weight. The compound represented by general formula (1) has the advantage of being easily soluble in organic solvents. Therefore, the compound represented by general formula (1) is easy to apply the coating method to, and is also easy to purify to increase its purity.

[0061] It is also conceivable that the present invention can be applied to use a compound containing a plurality of structures represented by general formula (1) in the molecule as a light-emitting material. For example, a polymerizable group may be pre-existed in the structure represented by general formula (1), and the polymer obtained by polymerizing the polymerizable group may be used as a light-emitting material. For example, a monomer containing a polymerizable functional group at any site of general formula (1) may be prepared, and the monomer may be polymerized alone or copolymerized with other monomers to obtain a polymer having repeating units, and the polymer may be used as a light-emitting material. Alternatively, compounds having a structure represented by general formula (1) may be coupled to obtain dimers or trimers, and these may be used as light-emitting materials.

[0062] 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. [ka]

[0063] In the above general formula, Q represents a group containing a structure represented by general formula (1), and 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, which 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. In the above general formula, R 101 , R 102 , R 103 and R 104 each independently represents a substituent, preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom, and still 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 can be bonded to any site of general formula (1) constituting Q. Two or more linking groups may be bonded to one Q to form a crosslinked structure or a network structure.

[0064] Specific structural examples of the repeating unit include structures represented by the following formulas. [ka]

[0065] A polymer having repeating units containing these formulae 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. [ka]

[0066] 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. The repeating units having the structure represented by general formula (1) contained in the polymer may be of a single type, or may be of two or more types. Examples of repeating units not having the structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. For example, repeating units derived from monomers having an ethylenically unsaturated bond, such as ethylene and styrene, can be mentioned.

[0067] In some embodiments, the compound represented by general formula (1) is a light-emitting material. In one embodiment, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence. In certain embodiments of the present disclosure, the compounds represented by general formula (1) 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 when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) 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) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) 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) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) can emit light in the green region of the visible spectrum (e.g., from about 490 nm to about 575 nm, about 510 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, the compounds represented by general formula (1) are capable of emitting 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 certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the ultraviolet spectral region (e.g., 280-400 nm) when excited by thermal or electronic means. In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the infrared spectral region (eg, 780 nm to 2 μm) when excited by thermal or electronic means. In an embodiment of the present disclosure, an organic semiconductor device can be fabricated using a compound represented by general formula (1). The organic semiconductor device referred to here may be an organic optical device in which light is mediated, or an organic device in which light is not mediated. The organic optical device may be an organic light-emitting device that emits light, an organic light-receiving device that receives light, or an element in which light-mediated energy transfer occurs within the device. In an embodiment of the present disclosure, an organic optical device such as an organic electroluminescence device or a solid-state imaging device (e.g., a CMOS image sensor) can be fabricated using a compound represented by general formula (1). In an embodiment of the present disclosure, a CMOS (complementary metal-oxide semiconductor) can be fabricated using a compound represented by general formula (1).

[0068] The electronic properties of small molecule chemical libraries can be calculated using well-known ab initio quantum chemical calculations. For example, the Hartree-Fock equations can be solved using time-dependent density functional theory (TD-DFT / B3LYP / 6-31G*) with a basis set of functions known as 6-31G*, Becke's three-parameter, and Lee-Yang-Parr hybrid functionals to screen for molecular fragments (moieties) with HOMOs above a certain threshold and LUMOs below a certain threshold. Thus, the donor moiety ("D") can be selected for its HOMO energy (e.g., ionization potential) of, for example, -6.5 eV or greater, and the acceptor moiety ("A") can be selected for its LUMO energy (e.g., electron affinity) of, for example, -0.5 eV or less. 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 tightly restricts the acceptor and donor moieties to specific configurations. In some embodiments, the compound library is screened using one or more of the following properties: 1. Emission around a specific wavelength 2. Calculated triplet states above a specific energy level 3. Delta E below a certain value ST value 4. Quantum yield above a certain value 5.HOMO level 6.LUMO level In one embodiment, the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K (ΔE ST ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In some embodiments, ΔE ST The value is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV. In certain embodiments, the compounds represented by general formula (1) exhibit 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.

[0069] [Method for synthesizing the compound represented by general formula (1)] The compounds represented by general formula (1) include novel compounds. The compound represented by general formula (1) can be synthesized by combining known reactions. 1 ~R 5 In the case where two or more of the donor groups are fluorine atoms, a compound of general formula (1) in which a substituted or unsubstituted carbazole-9-yl group is the donor group can be synthesized by reacting a precursor in which the donor group is a fluorine atom with a substituted or unsubstituted carbazole. For details of the reaction conditions, please refer to the synthesis examples described below.

[0070] [Constructs using compounds represented by general formula (1)] In some embodiments, the 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, the compounds of Formula (1) may be combined with an electroactive material to form a film. In some cases, the compounds of Formula (1) may be combined with a hole transporting polymer. In some cases, the compounds of Formula (1) may be combined with an electron transporting polymer. In some cases, the compounds of Formula (1) may be combined with a hole transporting polymer and an electron transporting polymer. In some cases, the compounds of Formula (1) may be combined with a copolymer having both a hole transporting moiety and an electron transporting moiety. In these embodiments, electrons and / or holes formed in the solid film or layer may interact with the compounds of Formula (1).

[0071] [Film formation] In one embodiment, 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. Wet processes include, but are not limited to, spin coating, slit coating, inkjet printing (spraying), gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In one embodiment, 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, the dry process can be a vacuum deposition process, but is not limited thereto. When a vacuum deposition process is used, the compounds constituting the film can be co-deposited from separate deposition sources, or from a single deposition source containing a mixture of compounds. When a single deposition source is used, a mixed powder of compound powders can be used, a compressed compact of the mixed powder can be used, or a mixture of the compounds can be used by heating, melting, and cooling. 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 with a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source. By mixing multiple compounds in the same composition ratio as the composition ratio of the film to be formed and using the deposition source as a deposition source, a film with a desired composition ratio can be easily formed. In some embodiments, the temperature at which each of the co-deposited compounds has the same weight loss rate can be identified, and that temperature can be used as the temperature during co-deposition.

[0072] [Examples of use of the compound represented by formula (1)] The compound represented by the general formula (1) is useful as a material for organic light-emitting devices, and is particularly preferably used for organic light-emitting diodes. Organic Light-Emitting Diode: One aspect of the present invention relates to the use of a compound represented by general formula (1) of the present invention as an emitting material in an organic light-emitting device. In some embodiments, the compound represented by general formula (1) of the present invention can be effectively used as an emitting material in the emitting layer of an organic light-emitting device. In some embodiments, the compound represented by general formula (1) includes a delayed fluorescent material (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 a compound represented by general formula (1) as a delayed fluorescent material. In some embodiments, the compound represented by general formula (1) can be used as a host material and can be used together with one or more emitting materials, which may be fluorescent materials, phosphorescent materials, or TADF materials. In some embodiments, the compound represented by general formula (1) can also be used as a hole transport material. In some embodiments, the compound represented by general formula (1) can be used as an electron transport material. 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 containing the compound as an emitting material emits delayed fluorescence and exhibits high light emission efficiency. In some embodiments, the light-emitting layer comprises a compound represented by Formula (1), and the compound represented by 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 Formula (1) relative to the film-forming surface influences or dictates 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 Formula (1) improves light extraction efficiency from the light-emitting layer. One aspect of the present invention relates to an organic light-emitting device. In one embodiment, the organic light-emitting device includes an emitting layer. In one embodiment, the emitting layer includes a compound represented by general formula (1) as an emitting material. In one embodiment, the organic light-emitting device is an organic photoluminescence device (organic PL device). In one embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device). In one embodiment, the compound represented by general formula (1) assists the light emission of other emitting materials included in the emitting layer (as a so-called assist dopant). In one embodiment, the compound represented by general formula (1) included in the emitting layer has its lowest excited singlet energy level, which is between the lowest excited singlet energy level of the host material included in the emitting layer and the lowest excited singlet energy level of the other emitting materials included in the emitting layer. In some embodiments, the organic photoluminescent device includes at least one light-emitting layer. In some embodiments, the organic electroluminescent device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In some embodiments, the organic layer includes at least an light-emitting layer. In some embodiments, the organic layer includes only an light-emitting layer. In some embodiments, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In some embodiments, the hole transport layer may be a hole injection transport layer with hole injection functionality, and the electron transport layer may be an electron injection transport layer with electron injection functionality.

[0073] Emitting layer: In some embodiments, the light-emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons, hi 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 singlet and triplet excited 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, the singlet and triplet excitons are not sufficiently confined while still achieving high light emission efficiency. That is, any host material that can achieve 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.

[0074] When the compound represented by general formula (1) is used as an assist dopant, various compounds can be used as the light-emitting material (preferably a fluorescent material). Examples of such light-emitting 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. Furthermore, these exemplary skeletons may be combined with each other. Examples of light-emitting materials that can be used in combination with the assist dopant having the structure represented by general formula (1) are given below.

[0075] [ka] JPEG2024123555000087.jpg228162JPEG2024123555000088.jpg223170JPEG2024123555000089.jpg57167

[0076] 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).

[0077] Further preferred light-emitting materials include compounds represented by the following general formula (2). [ka]

[0078] 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. X 2 ~X 4 Of these, X 3 and X 4 At least one of the 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 of the two ends 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.

[0079] In one aspect of the present invention, X 2 When is O or NR, R 7 is an acceptor group or R 6 and R 7 are bonded to each other to form an acceptor group, or R 7 and R 8 are bonded to each other to form an acceptor group. 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 are bonded to each other to form an acceptor group. 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 are bonded to each other to form an acceptor group. 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 16In one embodiment of the present invention, when X is directly bonded to the carbon atom to which X is bonded to form a carbazole ring, at least one of the 3-position and the 6-position of the carbazole ring is substituted with an acceptor group. 1 is NR, R is a substituted or unsubstituted phenyl group, and R 1 When a carbazole ring is formed by directly bonding to the carbon atom to which the phenyl group is bonded, the 3-position of the carbazole ring is substituted with an acceptor group (where the 3-position is on the phenyl group). In one embodiment of the present invention, the compound is represented by the following general formula (2a): [ka]

[0080] 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. R 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. X 2 ~X 4 Of these, X 3 and X 4At least one of the groups is O or NR, and the remaining groups may be O or NR or may not be linked. When they are not linked, each of the two ends independently represents a hydrogen atom, a deuterium atom, or a substituent. Ar 1 and Ar 2 Each of the groups independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 , C.R. 3 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 , C.R. 10 , C.R. 11 , C.R. 14 , C.R. 15 , C.R. 16 may be substituted with N.

[0081] Further preferred light-emitting materials include compounds represented by the following general formula (3). [ka]

[0082] 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 , R10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 1 may be bonded to each other to form a cyclic structure. 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 , C.R. 10 , C.R. 11 , C.R. 12 , C.R. 13 , C.R. 14 , C.R. 15 , C.R. 16 may be substituted with N.

[0083] 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.

[0084] Further preferred light-emitting materials include compounds represented by the following general formula (4). [ka]

[0085] 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, provided that Z 1 , Z 2 , R 1 and R 2 are bonded to each other to form a ring, R 2 and R 3 are bonded to each other to form a ring, R 4 and R 5 are bonded to each other to form a ring, and R 5 and R 6 at least one of the rings formed by bonding together is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole, and R 1 ~R 9 At least one of Z is a substituted or unsubstituted aryl group or an acceptor group, or 1 and Z 2 At least one of the 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.

[0086] In one aspect of the present invention, Z 1 and Z 2 are each independently a substituted or unsubstituted non-fused benzene ring, a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring. 1 ~R 9 are each independently a substituted or unsubstituted aryl group or an acceptor group, or R 1 and R 2 are bonded to each other to form a ring, R 2 and R 3 are bonded to each other to form a ring, R 4 and R 5 are bonded to each other to form a ring, and R 5 and R 6 and R are bonded to each other to form a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or a pyrrole ring fused with a substituted or unsubstituted benzene ring. 8 is a substituted or unsubstituted aryl group or an acceptor group. In one embodiment of the present invention, the compound contains two or more rings selected from the group consisting of a benzofuran ring, a benzothiophene ring, and an indole ring.

[0087] Further preferred light-emitting materials include compounds having a fused ring structure A (in which hydrogen atoms may be substituted with deuterium atoms or substituents) 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. [ka]

[0088] 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, and Z and X 2 may be bonded to each other to form a cyclic structure. In the fused ring structure A, the structure fused to b and X 1 , b and Z, Z and X 2 may be bonded to each other to form a cyclic structure.

[0089] Further preferred light-emitting materials include compounds represented by the following general formula (5). [ka]

[0090] In general formula (5), Z 1represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 2 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, and R 2 and R 3 Each of Z 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 ring structure, provided that R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one pair of these is bonded to each other to form a ring structure.

[0091] Further preferred light-emitting materials include compounds represented by the following general formula (6). [ka]

[0092] In general formula (6), X 3 represents an oxygen atom or a sulfur atom, and 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, and R 2 and R 3 R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 2and 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 ring structure, provided that R 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.

[0093] Further preferred light-emitting materials include compounds represented by the following general formula (7). [ka]

[0094] In general formula (7), X 4 represents an oxygen atom or a sulfur atom, and 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, and 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 ring structure, provided that R2 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.

[0095] Further preferred light-emitting materials include compounds represented by the following general formula (8). [ka]

[0096] In 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, and 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.

[0097] Further preferred light-emitting materials include compounds represented by the following general formula (9). [ka]

[0098] In general formula (9), Z 1 and Z 4 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 3 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 15 ~R 17 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 3 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and R 1 , Z 4 and R 15 , R 15 and R 16 , R 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.

[0099] Further preferred light-emitting materials include compounds represented by the following general formula (10). [ka]

[0100] 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 1represents a hydrogen atom, a deuterium atom or a substituent, and R 2 and R 3 Each of Z independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and R 1 , R 2 and Z 5 , Z 5 and Z 3 , Z 3 and R 3 may be bonded to each other to form a ring structure, provided that R 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.

[0101] Further preferred light-emitting materials include compounds represented by the following general formula (11). [ka]

[0102] In 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, and 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 , R23 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.

[0103] Further preferred light-emitting materials include compounds represented by the following general formula (12). [ka]

[0104] In general formula (12), Z 1 and Z 6 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 2 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 and R 28 ~R 30 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 2 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 2 and Z 2 , Z 2 and R 28 , R 28 and R 29 , R 29 and R 30 , R 30 and Z 6 may be bonded to each other to form a cyclic structure.

[0105] Further preferred light-emitting materials include compounds represented by the following general formula (13). [ka]

[0106] In 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, and R 2 and R 3 R each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 2 and Z 2 , Z 2 and Z 7 , Z 7 and R 3 may be bonded to each other to form a ring structure, provided that R 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.)

[0107] Further preferred light-emitting materials include compounds represented by the following general formula (14). [ka]

[0108] In 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, and 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.

[0109] Further preferred light-emitting materials include compounds represented by the following general formula (15). [ka]

[0110] In 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 55and 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.

[0111] Further preferred light-emitting materials include compounds represented by the following general formula (16). [ka]

[0112] In general formula (16), Z 1 , Z 8 and Z 9 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R 1 and R 61 ~R 66 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and Z 1 , Z 9 and R 61 , R 61 and R 62 , R 62 and R 63 , R 63 and R 64 , R 64 and R 65 , R 65 and R 66 , R 66 and Z 8 may be bonded to each other to form a cyclic structure.

[0113] Further preferred light-emitting materials include compounds represented by the following general formula (17). [ka]

[0114] In 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.

[0115] Further preferred light-emitting materials include compounds represented by the following general formula (18). [ka]

[0116] (In the general formula (18), Z 1 , Z 11 and Z 12 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R 1 and R 72 ~R 74 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 71represents 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.

[0117] Further preferred light-emitting materials include compounds represented by the following general formula (19). [ka]

[0118] In the general formula (19), Z 1 and Z 11 each independently represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; R 1 and R 76 ~R 82 each independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; R 75 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 1 and Z 1 , R 75 and Z 11 , Z 11 and R 76 , R 76 and R 77 , R 77 and R 78 , R 78 and R 79 , R 79 and R 80 , R 80 and R 81 , R 81 and R 82may be bonded to each other to form a cyclic structure.

[0119] Further preferred light-emitting materials include compounds represented by the following general formula (20). [ka]

[0120] 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, and R 101 ~R 130 each independently represents a hydrogen atom, a deuterium atom, or a substituent; R 101 and R 102 , R 102 and R 103 , R 103 and R 104 , R 104 and R 105 , R 105 and R 106 , R 106 and R 107 , R 107 and R 108 , R 108 and R 109 , R 109 and R 110 , R 110 and R 111 , R 111 and R 112 , R 112 and R 113 , R 113 and R 114 , R 114 and R 115 , R 115 and R 116 , R 116 and R 117 , R 117 and R 118 , R 118 and R 119 , R 119 and R 120 , R 120 and R 121 , R 121 and R 122 , R122 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.

[0121] Further preferred light-emitting materials include compounds represented by the following general formula (21). [ka]

[0122] 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, provided that R 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 , Z2 and R 2 , R 2 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 1 may be bonded to each other to form a cyclic structure. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 may be substituted with N.

[0123] 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.

[0124] Further preferred light-emitting materials include compounds represented by the following general formula (22). [ka]

[0125] In 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 24and R 25 , R 25 and R 26 may be bonded to each other to form a cyclic structure. 1 is a nitrogen atom, R 17 and R 18 are bonded to each other as a single bond to form a pyrrole ring, and X 2 is a nitrogen atom, R 21 and R 22 are bonded to each other to form a single bond to form a pyrrole ring. 1 is a nitrogen atom, and R 7 and R 8 and R 21 and R 22 are bonded via a nitrogen atom to form a six-membered ring, and R 17 and R 18 When they 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 R 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.

[0126] 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 combination of two or more groups. 8 and R 12 In one embodiment of the present invention, the compound is represented by the following general formula (1a). [ka]

[0127] 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 42 Each of m1 and m2 independently represents an integer of 0 to 5, each of n1 and n3 independently represents an integer of 0 to 4, and each of n2 and n4 independently represents an integer of 0 to 3. A 1 , A 2 each independently represents a hydrogen atom, a deuterium atom, or a substituent.

[0128] In one aspect of the present invention, A 1 and A 2 and each independently represents a group having a Hammett's σp value of greater than 0.2. 1 and A 2 In one embodiment of the present invention, A 1 and A 2 are both halogen atoms. In one embodiment of the present invention, the structure has a rotational symmetry.

[0129] Preferred specific examples of the compound having the above fused ring structure A and the compound represented by any one of general formulas (5) to (22) are given below. [ka] JPEG2024123555000115.jpg230162JPEG2024123555000116.jpg230159JPEG2024123555000117.jpg230159JPEG2024123555000118.jpg230170 JPEG2024123555000119.jpg230166JPEG2024123555000120.jpg230164JPEG2024123555000121.jpg230159JPEG2024123555000122.jpg131170 [ka] JPEG2024123555000124.jpg138170 [ka] JPEG2024123555000126.jpg186170

[0130] 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 of the light-emitting layer is an organic compound that has hole-transporting and electron-transporting functions. In some embodiments, the host material of the light-emitting layer is an organic compound that prevents the wavelength of emitted light from increasing. In some embodiments, the host material of the light-emitting layer is an organic compound that has a high glass transition temperature.

[0131] In some embodiments, the host material is selected from the group consisting of: [ka] In one embodiment, the light-emitting layer contains two or more 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 highest 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. 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 of 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 photo-excited luminescence quantum yield φPL1(A) of a co-deposited film of the first TADF molecules and the host material (where the concentration of the first TADF molecules in the co-deposited film is A wt %) and the photo-excited luminescence quantum yield φPL2(A) of a co-deposited film of the second TADF molecules and the host material (where the concentration of the second TADF molecules in the co-deposited film is A wt %) satisfy the relationship φPL1(A) > φPL2(A). In one embodiment, the photo-excited luminescence quantum yield φPL2(B) of a co-deposited film of the second TADF molecules and the host material (where the concentration of the second TADF molecules in the co-deposited film is B wt %) and the photo-excited luminescence quantum yield φPL2(100) of a film of the second TADF molecules alone satisfy the relationship φPL2(B) > φPL2(100). In some embodiments, the light-emitting layer may contain three structurally different TADF molecules, and the compound of the present invention may be any of the TADF compounds contained in the light-emitting layer. In some embodiments, the light-emitting layer can be composed of a material selected from the group consisting of a host material, an assist dopant, and a light-emitting material. In some embodiments, the light-emitting layer does not contain a metal element. In some embodiments, the light-emitting layer can be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. When the light-emitting layer contains a TADF material other than the compound of the present invention, the TADF material may 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 / 011955, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 081088, and ~0071 and 0118~0133, paragraphs 0009~0046 and 0093~0134 of JP 2013-256490 A, paragraphs 0008~0020 and 0038~0040 of JP 2013-116975 A, paragraphs 0007~0032 and 0079~0084 of WO2013 / 133359 A, paragraph 0 of WO2013 / 161437 A 008 to 0054 and 0101 to 0121, paragraphs 0007 to 0041 and 0060 to 0069 of JP 2014-9352 A, paragraphs 0008 to 0048 and 0067 to 0076 of JP 2014-9224 A, paragraphs 0013 to 0025 of JP 2017-119663 A, paragraphs 0013 to 0026 of JP 2017-119664 A, Compounds encompassed by the general formulas described in paragraphs 0012 to 0025 of JP 017-222623 A, paragraphs 0010 to 0050 of JP 2017-226838 A, paragraphs 0012 to 0043 of JP 2018-100411 A, and paragraphs 0016 to 0044 of WO 2018 / 047853 A, particularly exemplary compounds, that are capable of emitting delayed fluorescence are included.Further, here, the following patent documents are disclosed: JP 2013-253121 A, WO2013 / 133359 A, WO2014 / 034535 A, WO2014 / 115743 A, WO2014 / 122895 A, WO2014 / 126200 A, WO2014 / 136758 A, WO2014 / 133121 A, WO20 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.

[0132] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0133] Base material: In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate, and the substrate is not particularly limited and may be any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon.

[0134] 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 greater). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO, and ZnO. In some embodiments, an amorphous material capable of forming a transparent conductive film, such as In2O3-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 precise (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, the anode has a transmittance of greater than 10% when emitted light passes through it, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the anode has a thickness of 10 to 1,000 nm. In some embodiments, the anode has a thickness of 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0135] 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), alloy, conductive compound, or a combination thereof. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, indium, lithium-aluminum mixture, and rare earth elements. In some embodiments, a mixture of an electron-injecting metal and a second metal, which is a stable metal having a higher work function than the electron-injecting metal, is used. In some embodiments, the mixture is selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron-injecting properties and oxidation resistance. In some embodiments, the cathode is fabricated by forming the 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, one of the anode and 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 semi-transparent cathode. In some embodiments, a device includes an anode and a cathode, both of which are transparent or semi-transparent.

[0136] Injection layer: An injection layer is a layer between an electrode and an organic layer. In some embodiments, the injection layer reduces driving voltage and enhances 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. Preferred examples of compounds that can be used as hole injection materials are listed below.

[0137] [ka]

[0138] Next, preferred examples of compounds that can be used as the electron injection material will be listed. [ka]

[0139] Barrier layer: A blocking 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 blocking 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 functionality of an electron blocking layer and an exciton blocking layer.

[0140] Hole blocking layer: The hole blocking layer functions as an electron transport layer. In some embodiments, the hole blocking layer prevents holes from reaching the electron transport layer during electron transport. 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 can be the same materials as those described above for the electron transport layer. Preferred examples of compounds that can be used in the hole blocking layer are listed below.

[0141] [ka]

[0142] Electron barrier 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 can 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.

[0143] [ka]

[0144] 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 enables 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.

[0145] 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 hole injection or transport properties and electron blocking properties. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in 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 porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are listed below.

[0146] [ka]

[0147] 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.

[0148] [ka]

[0149] 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.

[0150] [ka]

[0151] 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.

[0152] device: In some embodiments, the light-emitting layer is incorporated into a device, including, but not limited to, an OLED bulb, an OLED lamp, a television display, a computer monitor, a mobile phone, and a tablet. 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 devices and / or as hole transport materials, such as 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-quench devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0153] Bulb or Lamp: In some embodiments, the 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 includes OLEDs of different colors. In some embodiments, the device includes an array including a combination of OLEDs. In some embodiments, the combination of OLEDs is a 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 comprises: 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 a light-emitting 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 comprises multiple OLEDs mounted on a circuit board such that light is emitted in multiple directions. In some embodiments, some 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.

[0154] Display or Screen: In some embodiments, the light-emitting layer of the present invention can be used in a screen or display. 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 onto 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 within the pixel area protects etching in specific regions until these specific patterns are undercut and removed from the substrate. At that point, all pixel areas are subjected to similar etch rates, but the 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 the pixel, enabling the deep, localized etching required to create steep vertical bevels. The preferred material for the deposition mask is Invar, a metal alloy that is cold-rolled into long, thin sheets at steel mills. Invar cannot be electrodeposited onto the spin mandrel as a nickel mask. A suitable, low-cost method for forming open areas in the 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.

[0155] 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 mother panel. OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarizing film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel.

[0156] In another aspect of the present invention, there is provided a method for manufacturing an organic light emitting diode (OLED) display, the method comprising: forming a barrier layer on a base substrate of the mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer over each of the display units of the cell panel; and applying an organic film to the interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example, made of SiNx, and the edges of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film helps the mother panel to be softly cut into individual cell panels. 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 formed of the same material as the planarization film and is formed simultaneously with the planarization film. In some embodiments, the light-emitting unit is connected to the TFT layer by a passivation layer, the planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting unit. In some embodiments of the manufacturing method, the organic film is not connected to either the display unit or the encapsulation layer.

[0157] 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 the 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 is formed of polyimide or acrylic, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of an 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 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.

[0158] In some embodiments, the light-emitting layer comprises a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode, hi some embodiments, the pixel electrode is coupled 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, a suitable voltage is formed between the pixel electrode and the counter electrode, which causes the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image-forming unit having a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, the encapsulation layer that covers the display units 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 an interval with each of the multiple display units. In some embodiments, the organic film is formed in such a manner that a portion of the organic film directly contacts the base substrate and the remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

[0159] In one embodiment, the OLED display is flexible and uses a flexible base substrate formed of polyimide, hi some embodiments, the base substrate is formed on a carrier substrate formed of a glass material, and the carrier substrate is then 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.

[0160] 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 the base substrate. In some embodiments, the TFT layer of each cell panel is formed, and a passivation layer (an inorganic film) and a planarization film (an organic film) are disposed on and cover the TFT layer. At the same time as the planarization film (e.g., polyimide or acrylic) is formed, the grooves at the interface are covered with an organic film (e.g., 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 impacts that may occur. That is, if all barrier layers were completely exposed without the organic film, the impacts would be transmitted to the barrier layers when each cell panel was 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 impacts that would otherwise be transmitted to the barrier layers, allowing each cell panel to be cut softly and preventing cracks from occurring in the barrier layers. In one embodiment, the organic film and the planarizing film covering the groove of the interface portion are spaced apart from each other. For example, if the organic film and the planarizing film are connected to each other as one layer, external moisture may penetrate into the display unit through the planarizing film and the remaining portion of the organic film, so the organic film and the planarizing film are spaced apart from each other so that the organic film is spaced apart from the display unit.

[0161] In some embodiments, the display unit is formed by forming a light-emitting unit, and an encapsulation layer is disposed on the display unit to cover the display unit. Thus, after the mother panel is completely manufactured, the carrier substrate carrying the base substrate is separated from the base substrate. In some embodiments, when a laser beam is irradiated onto the carrier substrate, the carrier substrate is separated 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 interface between the cell panels using a cutter. In some embodiments, the grooves at the interface along which the mother panel is cut are covered with an organic film, which absorbs shock during cutting. In some embodiments, this can prevent cracks from occurring in the barrier layer during cutting. In some embodiments, the method reduces product rejection rates and stabilizes product quality. Another embodiment is an OLED display having a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic film applied to the edges of the barrier layer. [Example]

[0162] The following synthesis examples and working examples will further illustrate the features of the present invention. The materials, processing details, processing procedures, etc. described 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 described below. The emission characteristics were evaluated using a source meter (Keithley: 2400 Series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics: C4334). The HOMO and LUMO energies were measured by atmospheric photoelectron spectroscopy (Riken Keiki AC-3, etc.). In the following synthesis examples, compounds within the general formula (1) were synthesized.

[0163] (Synthesis Example 1) Synthesis of Compound 727 [ka]

[0164] Compound X1 Carbazole-1,2,3,4,5,6,7,8-d8 (3.3 g, 18.8 mmol), p-bromoiodobenzene (7.9 g, 27.9 mmol), potassium carbonate (10.2 g, 73.8 mmol), and copper powder (2.4 g, 37.7 mmol) were heated in N,N-dimethylformamide (DMF: 50 mL) at 130 °C under a nitrogen atmosphere. After cooling to room temperature, the mixture was filtered through Celite and washed with ethyl acetate. The filtrate was concentrated and purified by silica gel chromatography (hexane) to obtain 5.7 g (17.2 mmol, 92% yield) of compound X1 as a white solid. 1 H NMR (400 MHz, CDCl3): δ 7.73 (dt, J = 9.2, 2.0 Hz, 2H) 7.46 (dt, J = 8.8, 2.8 Hz, 2H). ASAP MS Spectral Analysis: C 18H4D8BrN: Calculated 329.07, Observed 330.12 [M+H + ]

[0165] [ka]

[0166] Compound X2 Under a nitrogen stream, a tetrahydrofuran solution (55 mL of THF solution) of Mg (0.48 g, 19.7 mmol) and compound X1 (5.5 g, 16.7 mmol) was heated to 60°C and stirred for 3 hours. The resulting brown solution was cooled to room temperature and slowly added dropwise to a 55 mL of THF solution of 2,4-dichloro-6-(phenyl-2,3,4,5,6-d5)-1,3,5-triazine (3.82 g, 16.5 mmol). After the addition was complete, the temperature was raised to room temperature and stirred for 3 hours. The reaction vessel was cooled to 0°C, and saturated aqueous ammonium chloride solution (200 mL) was added. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and then dried over anhydrous magnesium. The solvent was removed, and the residue was purified by silica gel chromatography (hexane / toluene = 6:1) to obtain 1.76 g (3.92 mmol, 23% yield) of compound X2 as a pale yellow solid. 1 H NMR (400 MHz, CDCl3): δ 8.88 (dt, J = 8.8, 2.0 Hz, 2H), 7.82 (dt, J = 8.4, 2.0 Hz, 2H). ASAP MS Spectral Analysis: C 27 H4D 13 ClN4: Calculated 445.20, Observed 446.27 [M+H + ]

[0167] [ka]

[0168] Compound X3 Under a nitrogen stream, a 2.0 M solution of isopropylmagnesium chloride in THF (1.2 mL, 2.4 mmol) was slowly added dropwise to a solution of 5-bromo-2,3,4-trifluorobenzonitrile (0.47 g, 2.0 mmol) in THF (8 mL) at -78 °C. After stirring for 1 hour, a 1 M solution of zinc chloride in THF (6 mL, 6 mmol) was added and stirred for an additional 30 minutes. The mixture was then warmed to room temperature, and compound X2 (0.60 g, 1.3 mmol), tetrakis(triphenylphosphine)palladium(0) (0.79 g, 0.068 mmol), and THF (5 mL) were added. The mixture was then warmed to 80 °C and stirred for 17 hours. After cooling to room temperature, the resulting solid was washed with ion-exchanged water, methanol, ethyl acetate, and hexane to obtain 0.623 g (1.09 mmol, 81% yield) of compound X3 as a yellow solid. ASAP MS Spectral Analysis: C 34 H5D 13 F3N5: Calculated 566.23, Observed 567.39 [M+H + ]

[0169] [ka]

[0170] Compound 727 Potassium carbonate (0.980 g, 7.06 mmol) was added to a DMF (29 mL) solution of compound X3 (1.00 g, 1.76 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (1.08 g, 6.17 mmol), and the mixture was stirred at 110°C for 20 hours under a nitrogen atmosphere. The reaction solution was cooled to room temperature, saturated aqueous ammonium chloride was added, and the mixture was extracted with methylene chloride. The organic layer was washed with ion-exchanged water and saturated brine, and then dried over anhydrous magnesium sulfate. The resulting solid was purified by silica gel chromatography (hexane / methylene chloride = 1:1). The resulting solid was washed with methanol and then reprecipitated with methylene chloride / methanol to obtain 1.08 g (1.05 mmol, 59% yield) of compound 727 as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 9.08 (s, 1H), 8.08 (d, J = 8.8 Hz, 2H), 7.51 (d, J = 8.8 Hz, 2H). ASAP MS Spectral Analysis: C 70 H5D 37 N8: Calculated value 1031.59, observed value 1032.82 [M+H + ]

[0171] (Synthesis Example 2) Synthesis of Compound 727 (28) [ka]

[0172] Compound X4 Under a nitrogen stream, a 1.0 M solution of diisobutylaluminum hydride in toluene (DIBAL-H in toluene: 0.60 mL, 0.60 mmol) was added to a mixture of magnesium (1.53 g, 63 mmol) and 20 mL of THF, followed by the slow dropwise addition of a 1.0 M solution of 3-bromo-9-(phenyl-2,3,4,5,6-d5)-9H-carbazole (20.3 g, 62 mmol) in THF (80 mL) at 45 °C. After the addition, the mixture was heated to 70 °C and stirred for an additional 2 hours. The resulting brown solution was cooled to room temperature and slowly added dropwise to a 120 mL solution of 2,4-dichloro-6-(phenyl-2,3,4,5,6-d5)-1,3,5-triazine in THF at 0 °C. After the addition, the mixture was allowed to warm to room temperature and stirred for 18 hours. The reaction vessel was cooled to 0°C, saturated aqueous ammonium chloride solution (100 mL) was added, and the organic and aqueous phases were separated. The organic phase was concentrated, and the resulting solid was washed with THF and hexane. The solid was dissolved in hot toluene, passed through a silica pad, and the filtrate was concentrated. The resulting pale yellow solid was washed with THF and hexane to obtain 13.0 g (29.3 mmol, 47% yield) of pale yellow compound X4. 1H-NMR (400 MHz, DMSO-d6): δ 9.49 (d, J=1.6 Hz, 1H), 8.65 (dd, J=8.8, 1.6 Hz, 1H), 8.55 (d, J=12 Hz, 1H), 7.51-7.54 (m, 2H), 7.388-7.424 (m, 2H). ASAP MS Spectral Analysis: C 27 H7D 10 ClN4: Calculated 442.18, Observed 443.39 [M+H + ]

[0173] [ka]

[0174] Compound X5 Under a nitrogen stream, a 2.0 M THF solution of isopropylmagnesium chloride (5.3 mL, 10.6 mmol) was slowly added dropwise to a THF (100 mL) solution of 5-bromo-2,4-difluorobenzonitrile (2.36 g, 10.0 mmol) at -78°C. After stirring for 1 hour, tributyltin chloride (3.96 g, 12.1 mmol) was added, and the mixture was stirred for 10 minutes. The temperature was then raised to room temperature and stirred for an additional 3 hours. The reaction vessel was cooled to 0°C, and saturated ammonium chloride solution was added. The resulting reaction solution was extracted with toluene, and the organic layer was washed with saturated brine and dried over anhydrous magnesium. The solvent was removed, and the resulting yellow liquid was dissolved in anhydrous toluene (100 mL). Bis(triphenylphosphine)palladium(II) dichloride (0.71 g, 1.0 mmol) and compound X4 (4.43 g, 10.0 mmol) were added, and the mixture was stirred at 120 °C for 15 hours. The reaction vessel was returned to room temperature, and the resulting gray solid was washed with toluene and hexane. The solid was dissolved in hot toluene and then passed through a silica pad, and the filtrate was concentrated. The resulting pale yellow solid was washed with a mixed solution of ethyl acetate and hexane, yielding 2.41 g (4.28 mmol, 43% yield) of compound X5 as a pale orange solid. ASAP MS Spectral Analysis: C 34 H8D 10F3N5: Calculated 563.21, Observed 564.39 [M+H + ]

[0175] [ka]

[0176] Compound 727(28) Potassium carbonate (1.42 g, 10.3 mmol) was added to a DMF (50 mL) solution of compound X5 (1.41 g, 2.50 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (1.49 g, 8.50 mmol) and the mixture was stirred at 130 °C for 5 hours. The reaction solution was cooled to room temperature and diluted with ethyl acetate. The solution was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the resulting solid was reprecipitated with ethyl acetate / hexane. The solid was filtered and washed with hexane and methanol. The crude product was purified by column chromatography (toluene / hexane = 4:1). The resulting solid was reprecipitated with ethyl acetate / hexane to give 1.83 g (1.78 mmol, 71% yield) of pale green compound 727 (28). 1 H-NMR (400 MHz, DMSO-d6): δ 9.36 (s, 1H), 9.05 (brs, 1H), 8.31 (d, J=8.4 Hz, 1H), 8.08 (d, J=8.4 Hz, 1H), 7.48-7.52 (m, 2H), 7.37-7.40 (m, 1H), 7.28 (d, J=8.4 Hz, 1H). ASAP MS Spectral Analysis: C 70 H8D 34 N8: Calculated value 1028.56, observed value 1029.88 [M+H + ]

[0177] (Synthesis Example 3) Synthesis of Compound 727 (252) [ka]

[0178] Compound X6 Under a nitrogen stream, a 1.0 M DIBAL-H toluene solution (0.21 mL, 0.21 mmol) was added to a mixture of Mg (0.54 g, 22.23 mmol) and THF (21 mL), followed by the slow dropwise addition of a 3.0 M THF solution (7 mL) of 3-bromo-9-(phenyl-2,3,4,5,6-d5)-9H-carbazole (7.2 g, 21.1 mmol) at 45 °C. After the addition, the mixture was heated to 70 °C and stirred for an additional 2 hours. The resulting brown solution was cooled to room temperature and then slowly added dropwise to a THF solution (33.6 mL) of 2,4,6-trichloro-1,3,5-triazine at room temperature. After the addition, the mixture was stirred at 30 °C for 15 hours. Saturated aqueous ammonium chloride solution (30 mL) was added and stirred for 15 hours. The reaction mixture was filtered, and the resulting solid was washed with hexane to obtain 3.3 g (8.3 mmol, yield 40%) of compound X6 as a pale yellow solid. 1 H-NMR (400 MHz, CDCl3): δ 9.33 (d, J=1.6 Hz, 1H), 8.55 (dd, J=2.0, 1.6 Hz, 1H), 8.27 (d, J=7.6 Hz, 1H), 7.37-7.51 (m, 4H). ASAP MS Spectral Analysis: C 21 H7D5Cl2N4: Calculated 395.08, Observed 396.11 [M+H + ]

[0179] [ka]

[0180] Compound X7 Under a nitrogen stream, a mixture of carbazole-1,2,3,4,5,6,7,8-d8 (0.63 g, 3.60 mmol) and 60 wt% sodium hydride (0.14 g, 3.60 mmol) was added to THF (10 mL) and stirred at room temperature for 1 hour. The resulting reaction mixture was slowly added dropwise to a THF solution (150 mL) of compound X6 (1.7 g, 4.28 mmol) at 0 °C. After the addition was complete, the mixture was stirred at room temperature for 1 hour. DMF (250 mL) was then added, and the mixture was stirred at 100 °C for 13 hours, followed by stirring at 110 °C for 4 hours. The reaction mixture was returned to room temperature, saturated aqueous ammonium chloride and methanol were added, and the resulting solid was filtered and washed with hexane to obtain 1.97 g (3.68 mmol, 86% yield) of compound X7 as a pale yellow solid. 1 H-NMR (400 MHz, CDCl3): δ 9.44 (d, J=1.6 Hz, 1H), 8.68 (dd, J=2.0, 1.6 Hz, 1H), 8.30 (d, J=3.6 Hz, 1H), 7.37-7.55 (m, 4H). ASAP MS Spectral Analysis: C 33 H7D 13 ClN5: Calculated 534.22, Observed 535.33 [M+H + ]

[0181] [ka]

[0182] Compound X8 Under a nitrogen stream, a 1.0 M solution of isopropylmagnesium chloride in THF (4.2 mL, 4.2 mmol) was slowly added dropwise to a solution of 5-bromo-2,3,4-trifluorobenzonitrile (0.9 g, 3.81 mmol) in THF (15 mL) at -78 °C. After stirring for 30 minutes, a 1.0 M solution of zinc chloride in THF (11.4 mL, 11.4 mmol) was added and stirred for 30 minutes. The mixture was then warmed to room temperature and stirred for 1 hour. Compound X7 (1.43 g, 2.67 mmol), tetrakistriphenylphosphinepalladium(0) (0.22 g, 0.19 mmol), and anhydrous toluene (38 mL) were added and stirred at 90 °C for 14 hours. The reaction vessel was returned to room temperature, saturated aqueous ammonium chloride solution and methanol were added, and the resulting solid was filtered and washed with hexane to obtain 0.64 g (0.97 mmol, 37% yield) of compound X8 as a pale yellow solid. ASAP MS Spectral Analysis: C 40 H8D 13 F3N6: Calculated 655.26, Observed 656.34 [M+H + ]

[0183] [ka]

[0184] Compound 727(252) Under a nitrogen stream, potassium carbonate (0.65 g, 3.05 mmol) was added to a solution of compound X8 (0.4 g, 0.61 mmol) and carbazole-1,2,3,4,5,6,7,8-d8 (0.44 g, 2.5 mmol) in DMF (20 mL) and stirred at 90 °C for 41 hours. The reaction solution was cooled to room temperature, stirred with saturated brine and methanol, and then filtered. The filtrate was concentrated, and the resulting solid was dissolved in chloroform and purified by column chromatography (toluene / hexane = 4:1) and column chromatography (toluene / hexane = 2:1). The resulting solid was washed with acetonitrile to obtain 0.40 g (0.356 mmol, 58% yield) of compound 727 (252) as a yellow-green solid. 1H-NMR (400 MHz, DMSO-d6): δ 8.98 (s, 1H), 8.55 (s, 1H), 7.90-7.95 (m, 2H), 7.21-7.43 (m, 4H). ASAP MS Spectral Analysis: C 76 H8D 37 N9: Calculated value 1120.61, observed value 1121.88 [M+H + ]

[0185] (Example 1) Preparation and evaluation of thin films Vacuum deposition method on a quartz substrate at a vacuum level of 1 x 10 -3 Compound 727 was evaporated under conditions of less than 100 Pa to form a neat thin film of compound 727 with a thickness of 100 nm. Separately, a vacuum of 1×10 was deposited on a quartz substrate by vacuum deposition. -3 Compound 727 and H1 having the following structure were evaporated from different evaporation sources under conditions of less than 10 Pa, to form a doped thin film with a concentration of Compound 727 of 30 wt % to a thickness of 100 nm. Neat and doped thin films were prepared in the same manner using Compound 727(28) and Comparative Compound A instead of Compound 727. The photoluminescence of each doped thin film was analyzed when irradiated with 300 nm excitation light, and the proportion of delayed fluorescence components and the lifetime (τ2) of the delayed fluorescence components were measured. The HOMO and LUMO energies were also measured using each neat thin film. The results are shown in the table below. [Table 5] [ka]

[0186] (Example 2) Fabrication and evaluation of organic electroluminescence device Each thin film was deposited by vacuum deposition on a glass substrate with an anode made of indium tin oxide (ITO) with a thickness of 50 nm, at a vacuum of 5.0 × 10 -5The layers were deposited using a Pa process. First, a 10-nm thick HAT-CN film was deposited on ITO, followed by a 30-nm thick NPD film. A 10-nm thick TrisPCz film was then deposited on top of that, followed by a 5-nm thick H1 film. Next, H1, compound 727, and the dopant EM1 were co-evaporated from separate sources to form a 40-nm thick layer, which served as the emissive layer. The H1 concentration in the emissive layer was 34.2 wt%, the compound 727 concentration was 65 wt%, and the EM1 concentration was 0.8 wt%. Next, a 10-nm thick SF3-TRZ film was deposited, followed by co-evaporation of Liq and SF3-TRZ from separate sources to form a 30-nm thick layer. The Liq and SF3-TRZ concentrations in this layer were 30 wt% and 70 wt%, respectively. Further, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was vapor-deposited to a thickness of 100 nm to form a cathode, thereby completing an organic electroluminescence device. Each organic electroluminescence device was fabricated in the same manner as above, except that Compound 727(28) was used instead of Compound 727. When the external quantum efficiency (EQE) of each organic electroluminescence device was measured, all of them showed high values ​​exceeding 20%, confirming the usefulness of the compound represented by general formula (1).

[0187] [ka]

[0188] (Example 3) ΔE ST Rating Quantum chemical calculations were performed using B3LYP-631G on Compound 727 and Compound 6677 synthesized in Synthesis Example 1, and Comparative Compounds B and C having the following structures. The energy difference (ΔE ST The results are shown in the table below. [ka] [Table 6]

[0189] (Example 4) ΔE ST Rating Quantum chemical calculations were performed in the same manner as in Example 3 for Compound 727 (28), Compound 6677 (28), which were synthesized in Synthesis Example 2, and Comparative Compounds D and E having the following structures, to determine ΔE ST The results are shown in the table below. [ka] [Table 7]

[0190] The results in Tables 6 and 7 show the ΔE ST is smaller than that of the comparative compound, indicating that it is useful as a delayed fluorescent material. [Industrial Applicability]

[0191] By using the compound represented by general formula (1), an organic light-emitting device with good light-emitting properties can be provided, and therefore the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1): 【Chemistry 1】 [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 ~R ５ At least one of R is a cyano group; １ ~R ５ At least two of X are donor groups. 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 represents a group having a structure represented by the following general formula (c), (d), or (f): ２ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ represents a single bond or a divalent linking group. 【Chemistry 2】 [In general formula (c), each R independently represents a deuterium atom or a donor group. Ar 6 and Ar 7 independently represent a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Ar 6 and Ar 7 may be bonded to each other to form a cyclic structure, Ar 6 and R may be bonded to each other to form a cyclic structure, or Ar 7 and R may be bonded to each other to form a cyclic structure. n represents an integer of 0 to 4. * indicates a bonding position.] 【Transformation 3】 [In general formula (d), each R independently represents a deuterium atom or a donor group. Z 1 represents C-R 14 or N, Z 2 represents C-R 15 or N, Z 3 represents C-R 16 or N, and Z 4 represents C-R 17 or N. Z 5 represents C or N, and Ar 5 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 may be bonded to each other to form a cyclic structure. n represents an integer of 0 to 4. * indicates a bonding position.] 【Chemistry 4】 [In general formula (f), each R independently represents a deuterium atom or a donor group. Z 6 represents C-R 18 or N, Z 7 represents C-R 19 or N, Z 8 represents C-R 20 or N, and R 18 and R 19 , and R 19 and R 20 may be bonded to each other to form a cyclic structure. X is absent or represents a single bond, or represents a linking group having a linking chain of 1 or 2 atoms. Ar 7 represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. m represents an integer of 0 to 3. * indicates a bonding position.]

2. R １ ~R ５ The compound of claim 1 , wherein only one of

3. R ２ The compound of claim 2, wherein is a cyano group.

4. Ar １ The compound according to claim 1, wherein is a group having a structure represented by the following general formula (c): 【Transformation 5】 In the general formula (c), each R independently represents a deuterium atom or a donor group. ６ and Ar ７ Each of Ar independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. ６ and Ar ７ may be bonded to each other to form a ring structure, and Ar ６ and R may be bonded to each other to form a cyclic structure, and Ar ７ and R may be bonded to each other to form a cyclic structure. n represents an integer of 0 to 4. * indicates the bonding position.

5. Ar １ The compound according to claim 1, wherein is a group having a structure represented by the following general formula (d): 【Transformation 6】 In the general formula (d), each R independently represents a deuterium atom or a donor group. 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. n represents an integer of 0 to 4. * indicates the bonding position.

6. Ar １ The compound according to claim 1, wherein is a group having a structure represented by the following general formula (f): 【Transformation 7】 In the general formula (f), each R independently represents a deuterium atom or a donor group. ６ is C-R １８ or N, Z ７ is C-R １９ or N, Z ８ is C-R ２０ or N, R １８ and R １９ , R １９ and R 20 may be bonded to each other to form a cyclic structure. X is absent and represents a single bond, or represents a linking group having a linking chain of 1 or 2 atoms. ７ represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; m represents an integer of 0 to 3; * indicates the bonding position.

7. Ar ２ The compound according to claim 1 , wherein is a substituted or unsubstituted aryl group having no donor group.

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

9. Ar ２ The compound according to claim 1, wherein is a group having a structure represented by the following general formula (f): 【Transformation 8】 In the general formula (f), each R independently represents a deuterium atom or a donor group. ６ is C-R １８ or N, Z ７ is C-R １９ or N, Z ８ is C-R ２０ or N, R １８ and R １９ , R １９ and R 20 may be bonded to each other to form a cyclic structure. X is absent and represents a single bond, or represents a linking group having a linking chain of 1 or 2 atoms. ７ represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group; m represents an integer of 0 to 3; * indicates the bonding position.

10. R １ ~R ５ The compound of claim 1 , wherein three of the groups are donor groups.

11. The compound according to claim 1, wherein the donor group represented by R 1 to R 5 is a substituted or unsubstituted carbazol-9-yl group.

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

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

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

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

16. A light-emitting material comprising the compound according to any one of claims 1 to 15.

17. A delayed fluorescent material comprising the compound according to any one of claims 1 to 15.

18. A film comprising a compound according to any one of claims 1 to 15.

19. An organic semiconductor device comprising the compound according to any one of claims 1 to 15.

20. An organic light-emitting device comprising the compound according to any one of claims 1 to 15.

21. 21. The organic light-emitting device of claim 20, wherein the device has a layer comprising the compound, the layer also comprising a host material.

22. 22. The organic light-emitting element according to claim 21, 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.

23. 22. The organic light-emitting device of claim 21, wherein the device has a layer comprising the compound, the layer also comprising a light-emitting material having a structure different from that of the compound.

24. 22. The organic light-emitting device of claim 21, wherein the compound emits the greatest amount of light of any material contained in the device.

25. 24. The organic light-emitting device of claim 23, wherein the amount of light emitted from the light-emitting material is greater than the amount of light emitted from the compound.

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

27. The organic light-emitting device according to claim 20, which emits delayed fluorescence.

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