Compound, light-emitting material and light-emitting device

Abstract

A compound represented by the general formula herein is an excellent light-emitting material. R1 to R5 each represent a hydrogen atom, a deuterium atom, or a substituent other than a cyano group, with at least one among R1 to R5 being an aryl group or a pyridyl group, at least two or more among R1 to R5 being a donor group, and at least one of said donor groups being a substituted condensed-ring indol-1-yl group (the number of rings constituting the condensed ring being 4 or more).

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. Among these are many compounds in which a donor group is substituted on a cyanobenzene. As a typical compound, the following cyanobenzene substituted with a carbazol-9-yl group has been proposed (see Patent Document 1).

[0005] [ka] [Prior art documents] [Non-patent literature]

[0006] [Non-Patent Document 1] WO2018 / 155642A1 Summary of the Invention [Problem to be solved by the invention]

[0007] Even among materials that emit delayed fluorescence, materials with extremely good properties and no practical issues have not yet been provided. Therefore, it would be even more useful if a compound with higher luminous efficiency and shorter delayed fluorescence lifetime than the compound described in Patent Document 1 could be provided. However, it is generally extremely difficult to improve delayed fluorescence lifetime and durability while improving luminous efficiency. Furthermore, improvements to delayed fluorescence materials are still in the trial and error stage, and it is not easy to generalize the chemical structure of a useful luminescent material.

[0008] Under these circumstances, the present inventors have conducted extensive research with the aim of providing compounds that are more useful as light-emitting 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 light-emitting materials. [Means for solving the problem]

[0009] As a result of intensive research to achieve the above object, the present inventors have found that a cyanobenzene compound having a structure that satisfies certain conditions is useful as a light-emitting material. The present invention has been proposed based on this finding, and specifically has the following configuration.

[0010] [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, or a substituent other than a cyano group. 1 ~R 5 At least one of R is a substituted or unsubstituted aryl group or a substituted or unsubstituted pyridyl group. 1 ~R 5 At least two of the two or more donor groups are donor groups, and at least one of the two or more donor groups is a substituted ring-fused indol-1-yl group (the number of rings constituting the fused ring is 4 or more). 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 may be bonded to each other to form a cyclic structure. [2] The compound according to [1], wherein the substituted ring-fused indol-1-yl group is a substituted ring-fused carbazol-9-yl group. [3] The compound according to [1], wherein the substituted ring-fused indol-1-yl group is a ring-fused carbazol-9-yl group substituted with an aryl group or a heteroaryl group. [4] The compound according to [1], wherein the substituted ring-fused indol-1-yl group is a ring-fused carbazol-9-yl group substituted with an aryl group. [5] The compound according to any one of [1] to [4], wherein the substituted ring-fused indol-1-yl group is a carbazol-9-yl group fused with 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. [6] The compound according to any one of [1] to [4], wherein the substituted ring-fused indol-1-yl group is a carbazol-9-yl group having a ring fused thereto, the ring having one or more atoms selected from the group consisting of oxygen atoms and sulfur atoms as ring skeleton-constituting atoms. [7] R 1 ~R 5The compound according to any one of [1] to [6], wherein 2 to 4 of the 2 to 4 are substituted or unsubstituted ring-fused indol-1-yl groups, and the 2 to 4 substituted or unsubstituted ring-fused indol-1-yl groups are of two or more types. [8] The compound according to [7], wherein one of the two or more types is a substituted ring-fused indol-1-yl group and the other is an unsubstituted ring-fused indol-1-yl group. [9] The compound according to [7] or [8], wherein one of the two or more groups is a carbazol-9-yl group having a fused ring whose ring skeleton is constituted by one or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, and nitrogen atoms, and the other group is a carbazol-9-yl group having no fused ring.

[10] The compound according to [7] or [8], wherein one of the two or more groups is a substituted or unsubstituted carbazol-9-yl group, and the other group is a carbazol-9-yl group substituted with a substituent different from the substituted or unsubstituted carbazol-9-yl group.

[11] R 1 ~R 5 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted ring-fused indol-1-yl group.

[12] R 1 and R 5 is an unsubstituted ring-fused indol-1-yl group, and R 2 a ring-fused indol-1-yl group substituted with R 4 is a substituted or unsubstituted ring-fused indol-1-yl group, and R 3 The compound according to any one of [1] to

[11] , wherein is a substituted or unsubstituted aryl group.

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

[12] , which has a linear symmetric structure.

[14] R 3 The compound according to any one of [1] to

[13] , wherein only is a substituted or unsubstituted aryl group.

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

[14] .

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

[14] .

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

[14] .

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

[14] .

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

[14] .

[20] The organic light-emitting device according to

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

[21] The organic light-emitting element according to

[20] , 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.

[22] The organic light-emitting device according to

[20] , 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.

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

[20] to

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

[24] The organic light-emitting element according to

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

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

[19] to

[24] , which is an organic electroluminescence device.

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

[19] to

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

[0011] The compounds of the present invention are useful as light-emitting materials. The compounds of the present invention also include compounds that have high luminous efficiency, short delayed fluorescence lifetime, and excellent alignment. Furthermore, organic light-emitting devices using the compounds of the present invention include devices that have high luminous efficiency, long device lifetime, and excellent durability. [Brief explanation of the drawings]

[0012] [Figure 1] FIG. 2 is a schematic cross-sectional view showing an example of a layer structure of an organic electroluminescence element. DETAILED DESCRIPTION OF THE INVENTION

[0013] 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 ( 2 In 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, H is assumed to be bonded to the carbon atom constituting the ring skeleton at the omitted position. In the chemical structural formulas herein, deuterium atoms are represented by D.

[0014] [Compound represented by general formula (1)] [ka]

[0015] In general formula (1), R 1 ~R 5 each independently represents a hydrogen atom, a deuterium atom, or a substituent other than a cyano group. R 1 ~R 5 At least one of R is a substituted or unsubstituted aryl group or a substituted or unsubstituted pyridyl group. Hereinafter, a "substituted or unsubstituted aryl group or a substituted or unsubstituted pyridyl group" will be referred to as an Ar group. In one embodiment of the present invention, at least R 1 is an Ar group. In one aspect of the invention, at least R 2 is an Ar group. In one aspect of the invention, at least R3 is an Ar group. 1 ~R 5 In one embodiment of the present invention, the number of Ar groups among R 1 ~R 5 In one embodiment of the present invention, four of the R 1 ~R 5 Three of the groups are Ar groups. For example, R 1 , R 3 , R 5 is an Ar group. For example, R 2 , R 3 , R 4 is an Ar group. For example, R 1 , R 2 , R 3 is an Ar group. For example, R 1 , R 2 , R 4 is an Ar group. For example, R 1 , R 3 , R 4 is an Ar group. In one aspect of the invention, R 1 ~R 5 Two of the groups are Ar groups. For example, R 1 and R 2 is an Ar group. For example, R 1 and R 3 is an Ar group. For example, R 1 and R 4 is an Ar group. For example, R 1 and R 5 is an Ar group. For example, R 2 and R 3 is an Ar group. For example, R 2 and R 4 is an Ar group. In one aspect of the invention, R 1 ~R 5 In one preferred embodiment of the present invention, only one of R 3 In one aspect of the invention, R 2 In one aspect of the invention, R 1 Only the Ar group. R 1 ~R 5The 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, and is preferably a substituted or unsubstituted phenyl group. The substituent of the aryl group may be selected from the following Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. The substituent on the aryl group may be one group or a combination of two or more groups selected from the group consisting of a cyano group, an alkyl group (for example, having 1 to 20 carbon atoms) and an aryl group (for example, having 6 to 22 carbon atoms). R 1 ~R 5 The pyridyl group may be any of a 2-pyridyl group, a 3-pyridyl group, and a 4-pyridyl group, and may be a group fused with a ring or a group in which a hydrogen atom has been substituted. For the substituent, the explanation of the substituent for the aryl group above can be referred to. When a ring is further fused to the pyridyl group, the 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 in which these are further fused. 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 further 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.

[0016] Specific examples of Ar groups that can be used in general formula (1) are shown below. However, the Ar 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, D represents a deuterium atom, t-Bu represents a tert-butyl group, and * represents a bonding position.

[0017] [ka]

[0018] Ar2(d) to Ar14(d) and Ar22(d) to Ar25(d) are examples of compounds in which all hydrogen atoms bonded to the alkyl or phenyl groups, which are substituents in the above Ar2 to Ar14 and Ar22 to Ar25, have been replaced with deuterium atoms. Ar2(d) to Ar26(D) are examples of compounds in which all hydrogen atoms bonded to Ar2 to Ar26 have been replaced with deuterium atoms.

[0019] In general formula (1), R 1 ~R 5 At least two of the two or more donor groups are donor groups, and at least one of the two or more donor groups is a substituted ring-fused indol-1-yl group (the number of rings constituting the fused ring is 4 or more). That is, R 1 ~R 5At least one of the rings is a substituted ring-fused indol-1-yl group (the number of rings constituting the fused ring is 4 or more). Hereinafter, a "substituted or unsubstituted ring-fused indol-1-yl group (the number of rings constituting the fused ring is 4 or more)" is referred to as an IDL group. The number of rings constituting the fused ring is 4 or more means that at least two rings are fused to the indol-1-yl group. More specifically, at least one fused ring or at least two monocyclic rings are fused to the indol-1-yl group. Since a carbazol-9-yl group has a structure in which three rings are fused, in order to form an IDL group, it is necessary to use a carbazol-9-yl group in which at least one ring is fused. The number of rings constituting the fused ring in the IDL group is preferably 4 to 9, more preferably 4 to 7. In one embodiment of the present invention, the number of rings constituting the fused ring is 4. In one embodiment of the present invention, the number of rings constituting the fused ring is 5. In one embodiment of the present invention, the number of rings constituting the fused ring is seven.

[0020] In one aspect of the invention, at least R 5 is an IDL group. In one aspect of the invention, at least R 4 is an IDL group. In one aspect of the invention, at least R 3 is an IDL group. R 1 ~R 5 In one embodiment of the present invention, the number of IDL groups among R 1 ~R 5 In one aspect of the invention, four of R 1 ~R 5 Three of the groups are IDL groups. For example, R 1 , R 3 , R 5 is an IDL group. For example, R 2 , R 3 , R 4 is an IDL group. For example, R 3 , R 4 , R 5 is an IDL group. For example, R 2 , R 4 , R 5 is an IDL group. For example, R 2 , R3 , R 5 is an IDL group. In one aspect of the invention, R 1 ~R 5 Two of the groups are IDL groups. For example, R 4 and R 5 is an IDL group. For example, R 3 and R 5 is an IDL group. For example, R 2 and R 5 is an IDL group. For example, R 1 and R 5 is an IDL group. For example, R 3 and R 4 is an IDL group. For example, R 2 and R 4 is an IDL group. In one aspect of the invention, R 1 ~R 5 In one aspect of the invention, only one of R 5 is the only IDL group. In one aspect of the invention, R 4 is the only IDL group. In one aspect of the invention, R 3 is the only IDL group. In one aspect of the present invention, R 3 is an aryl group or a pyridyl group, and at least R 5 is an IDL group. In one aspect of the invention, R 3 is an aryl group or a pyridyl group, and at least R 4 is an IDL group. In one aspect of the invention, R 3 is an aryl group or a pyridyl group, and at least R 4 and R 5 is an IDL group. In one aspect of the invention, R 3 is an aryl group or a pyridyl group, and at least R 2 and R 5 is an IDL group. In one aspect of the invention, R 3 is an aryl group or a pyridyl group, and at least R 1 and R 5 is an IDL group. In one aspect of the invention, R 3 is an aryl group or a pyridyl group, and at least R 1 and R 4 and R5 is an IDL group. In one aspect of the invention, R 3 is an aryl group or a pyridyl group, and at least R 2 and R 4 and R 5 is an IDL group. In one aspect of the invention, R 3 is an aryl group or a pyridyl group, and R 1 and R 2 and R 4 and R 5 is the IDL group. In one aspect of the present invention, R 2 is an aryl group or a pyridyl group, and at least R 5 is an IDL group. In one aspect of the invention, R 2 is an aryl group or a pyridyl group, and at least R 4 is an IDL group. In one aspect of the invention, R 2 is an aryl group or a pyridyl group, and at least R 3 is an IDL group. In one aspect of the invention, R 2 is an aryl group or a pyridyl group, and at least R 1 is an IDL group. In one aspect of the invention, R 2 is an aryl group or a pyridyl group, and at least R 4 and R 5 is an IDL group. In one aspect of the invention, R 2 is an aryl group or a pyridyl group, and at least R 3 and R 5 is an IDL group. In one aspect of the invention, R 2 is an aryl group or a pyridyl group, and at least R 1 and R 5 is an IDL group. In one aspect of the invention, R 2 is an aryl group or a pyridyl group, and at least R 3 and R 4 is an IDL group. In one aspect of the invention, R 2 is an aryl group or a pyridyl group, and at least R 1 and R 4 is an IDL group. In one aspect of the invention, R 2is an aryl group or a pyridyl group, and at least R 1 and R 3 is an IDL group. In one aspect of the invention, R 2 is an aryl group or a pyridyl group, and at least R 3 and R 4 and R 5 is an IDL group. In one aspect of the invention, R 2 is an aryl group or a pyridyl group, and at least R 1 and R 4 and R 5 is an IDL group. In one aspect of the invention, R 2 is an aryl group or a pyridyl group, and at least R 1 and R 3 and R 4 is an IDL group. In one aspect of the invention, R 2 is an aryl group or a pyridyl group, and R 1 and R 3 and R 4 and R 5 is the IDL group. In one aspect of the present invention, R 1 is an aryl group or a pyridyl group, and at least R 5 is an IDL group. In one aspect of the invention, R 1 is an aryl group or a pyridyl group, and at least R 4 is an IDL group. In one aspect of the invention, R 1 is an aryl group or a pyridyl group, and at least R 3 is an IDL group. In one aspect of the invention, R 1 is an aryl group or a pyridyl group, and at least R 2 is an IDL group. In one aspect of the invention, R 1 is an aryl group or a pyridyl group, and at least R 4 and R 5 is an IDL group. In one aspect of the invention, R 1 is an aryl group or a pyridyl group, and at least R 3 and R 5 is an IDL group. In one aspect of the invention, R 1 is an aryl group or a pyridyl group, and at least R2 and R 5 is an IDL group. In one aspect of the invention, R 1 is an aryl group or a pyridyl group, and at least R 3 and R 4 is an IDL group. In one aspect of the invention, R 1 is an aryl group or a pyridyl group, and at least R 2 and R 4 is an IDL group. In one aspect of the invention, R 1 is an aryl group or a pyridyl group, and at least R 2 and R 3 is an IDL group. In one aspect of the invention, R 1 is an aryl group or a pyridyl group, and at least R 3 and R 4 and R 5 is an IDL group. In one aspect of the invention, R 1 is an aryl group or a pyridyl group, and at least R 2 and R 4 and R 5 is an IDL group. In one aspect of the invention, R 1 is an aryl group or a pyridyl group, and at least R 2 and R 3 and R 4 is an IDL group. In one aspect of the invention, R 1 is an aryl group or a pyridyl group, and R 2 and R 3 and R 4 and R 5 is the IDL group.

[0021] The IDL group has a ring-fused indole structure in which a ring is fused to indole. Indole has a structure in which a benzene ring and a pyrrole ring are fused, and it is preferable that at least a further ring is fused to the pyrrole ring. In one embodiment of the present invention, the ring is fused only to the pyrrole ring. In one embodiment of the present invention, the ring is fused to both the pyrrole ring and the benzene ring. 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 in which these are further fused. Preferably, it is an aromatic hydrocarbon ring or an aromatic heterocycle. Examples of aromatic hydrocarbon rings include substituted or unsubstituted benzene rings. The benzene ring may be further 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, and 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 can be used as the aromatic heterocycle. In one embodiment of the present invention, the fused ring 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. It is preferable that a substituent selected from Substituent Group E is bonded to the nitrogen atom of the pyrrole ring, and more preferably, the pyrrole ring is substituted with an aryl group which may be substituted with an alkyl group or an aryl group.

[0022] In one embodiment of the present invention, the IDL group is a substituted ring-fused carbazol-9-yl group. In one embodiment of the present invention, the IDL group is a ring-fused carbazol-9-yl group substituted with an aryl group. In one embodiment of the present invention, the IDL group is a ring-fused carbazol-9-yl group substituted with a heteroaryl group. In one embodiment of the present invention, the IDL group is a carbazol-9-yl group having a ring fused thereto with one or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, and nitrogen atoms as ring skeletal constituent atoms. In one embodiment of the present invention, the IDL group is a carbazol-9-yl group having a ring fused thereto with one or more atoms selected from the group consisting of oxygen atoms and sulfur atoms as ring skeletal constituent atoms. R 1 ~R 5 When two to four of R are IDL groups, the two to four IDL groups may be the same or different. 1 ~R 5 Among these, 2 to 4 are IDL groups, and the 2 to 4 IDL groups are composed of two or more types of IDL groups. For example, there may be two types. In one embodiment of the present invention, when two or more types of IDL groups are present, one of them is a carbazol-9-yl group having a fused ring with one or more atoms selected from the group consisting of oxygen atoms, sulfur atoms, and nitrogen atoms as ring skeleton-constituting atoms, and the other is a carbazol-9-yl group not having a fused ring. In one embodiment of the present invention, when two or more types of IDL groups are present, one of them is a substituted or unsubstituted carbazol-9-yl group, and the other is a different substituted or unsubstituted carbazol-9-yl group.

[0023] The IDL group is preferably a group represented by the following general formula (2). [ka]

[0024] In general formula (2), Z 1 is CR 11 or N, Z 2 is CR 12 or N, Z3 is CR 13 or N, Z 4 is CR 14 or N. Ar represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle. R 11 and R 12 , R 12 and R 13 , R 13 and R 14 may be bonded to each other to form a cyclic structure.

[0025] 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 11 ~R 14 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. 11 ~R 14 When two or more of R represent substituents, the two or more substituents may be the same or different. 11 ~R 14 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 11 ~R 14 R may be a hydrogen atom or a deuterium atom. 11 ~R 14 When is a hydrogen atom or a deuterium atom, Ar represents a substituted aromatic hydrocarbon ring or a substituted aromatic heterocycle. R 11 and R 12 , R 12 and R 13 , R13 and R 14 may be bonded to each other to form a cyclic structure. The cyclic structure may be any of an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, and an aliphatic heterocycle, or may be a condensed ring of 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 condensed with another benzene ring or may be condensed with a heterocycle such as a pyridine ring. The aromatic heterocycle 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 aromatic heterocycle. 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 11 and R 12 , R 12 and R 13 , R 13 and R 14 In one embodiment of the present invention, a pair of R 11 and R 12 , R 12 and R 13 , R 13 and R 14are not bonded to each other to form a ring structure.

[0026] In general formula (2), Ar represents a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle. In one embodiment of the present invention, Ar is a substituted or unsubstituted aromatic hydrocarbon ring, or a substituted or unsubstituted aromatic heterocycle. In one embodiment of the present invention, Ar is a substituted or unsubstituted aromatic heterocycle. An example of an aromatic hydrocarbon ring that Ar can take is a benzene ring. The benzene ring may be fused with another benzene ring or a heterocycle such as a pyridine ring. The aromatic heterocycle that Ar can take is preferably a 5- to 7-membered ring, and for example, a 5-membered ring or a 6-membered ring may be employed. In one embodiment of the present invention, the aromatic heterocycle may be a furan ring, a thiophene ring, a pyrrole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, or a pyrazine ring. In one embodiment of the present invention, the aromatic heterocycle 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. The benzofuran, benzothiophene, quinoline, and isoquinoline 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. When Ar is an unsubstituted aromatic hydrocarbon ring or an unsubstituted aromatic heterocycle, R 11 ~R 14 At least one of the groups is a substituent.

[0027] The IDL group is preferably a group represented by the following general formula (3). [ka]

[0028] In general formula (3), Z 1 is CR 11 or N, Z 2 is CR 12 or N, Z 3 is CR 13 or N, Z 4 is CR 14 or N, Z 6 is CR 16 or N, Z 7 is CR 17 or N, Z 8 is CR 18 or N, Z 9 is CR 19 or N. R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 may be bonded to each other to form a cyclic structure. Z in general formula (3) 1 ~Z 4 , R 11 ~R 14 For details of Z in general formula (3), please refer to the corresponding explanation for general formula (2). 6 ~Z 9 , R 16 ~R 19 is Z in general formula (2) 1 ~Z 4 , R 11 ~R 14 These correspond to Z in general formula (2). 1 ~Z 4 , R 11 ~R 14 The explanation of the general formula (3) can be referred to. 11 ~R 14 , R 16 ~R 19 At least one of is a substituent. 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 Among these, the number of N's is 0. When it is 0, it represents a substituted or unsubstituted carbazol-9-yl group. The carbazol-9-yl group may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. Substitution with an aryl group is preferred, as it is superior in terms of luminous efficiency and device life compared to substitution with a heteroaryl group. In a preferred embodiment of the present invention, the IDL group is a carbazol-9-yl group substituted with a group containing at least one substituted or unsubstituted aryl group, for example, a carbazol-9-yl group substituted with at least one substituted or unsubstituted aryl group. In one embodiment of the present invention, at least one of the 2- and 7-positions is a substituted or unsubstituted aryl group. In one embodiment of the present invention, at least one of the 3- and 6-positions is a substituted or unsubstituted aryl group. The aryl 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.

[0029] The ring-fused indol-1-yl group may be a monocyclic ring having one ring fused to the benzene ring or pyrrole ring constituting the indol-1-yl group, a polycyclic ring having one ring, or two or more polycyclic rings or a monocyclic ring. For example, when two rings are fused, it is preferable that one ring is fused to the benzene ring and the other ring is fused to the pyrrole ring. The two fused rings may be the same or different. A fused ring having four or more, five or more, or six or more rings may be formed by fusion of a ring to the indole ring. For example, a compound having a fused ring with four rings, a compound having a fused ring with five rings, a compound having a fused ring with six rings, a compound having a fused ring with seven rings, or a compound having a fused ring with eight rings may be used. The ring may be fused only to the 2- and 3-positions (b) of the indole ring, only to the 4- and 5-positions (e), only to the 5- and 6-positions (f), only to the 6- and 7-positions (g), or both to the 4- and 5-positions (e) and 6- and 7-positions (g). Also, the ring may be fused to any one of the 4- and 5-positions (e), 5- and 6-positions (f), and 6- and 7-positions (g) and to the 2- and 3-positions (b) (see the formula below, * indicates the bond position). [ka]

[0030] The ring directly fused to the benzene ring or pyrrole ring constituting the indol-1-yl group (when the fused ring is polycyclic, this refers to only the directly fused ring among the rings constituting the polycyclic ring) may be any of an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, and an aliphatic heterocycle. Preferably, one or more rings selected from the group consisting of a benzene ring and an aromatic heterocycle are directly fused. The heterocycle herein refers to a ring containing a heteroatom. The heteroatom is preferably selected from an oxygen atom, a sulfur atom, a nitrogen atom, and a silicon atom, and more preferably an oxygen atom, a sulfur atom, and a nitrogen atom. In a preferred embodiment, the heteroatom is an oxygen atom. In another preferred embodiment, the heteroatom is a sulfur atom. In yet another preferred embodiment, the heteroatom is a nitrogen atom. The number of heteroatoms contained as ring skeleton-constituting atoms of the heterocycle is one or more, preferably one to three, and more preferably one or two. In a preferred embodiment, the number of heteroatoms is one. When the number of heteroatoms is two or more, they are preferably the same type of heteroatom, but they may be composed of different types of heteroatoms. For example, the two or more heteroatoms may all be nitrogen atoms. The ring skeleton-constituting atoms other than the heteroatom are carbon atoms. The number of ring skeleton-constituting atoms of the heterocycle directly fused to the benzene ring constituting the indol-1-yl group is preferably 4 to 8, more preferably 5 to 7, and even more preferably 5 or 6. In a preferred embodiment, the heterocycle has five atoms constituting the ring skeleton. The heterocycle preferably has two or more conjugated double bonds, and the heterocycle preferably expands the conjugated system of the indole ring by condensation (i.e., preferably has aromaticity). Preferred examples of the heterocycle include a furan ring, a thiophene ring, and a pyrrole ring. The ring directly fused to the benzene ring or pyrrole ring constituting the indol-1-yl group may further be fused with another ring. The fused ring may be a monocyclic or fused ring. Examples of the fused ring include an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring. In a preferred embodiment of the present invention, at least one heterocyclic ring is directly fused to the benzene ring or pyrrole ring constituting the indol-1-yl group. In a preferred embodiment of the present invention, the fused ring constituting the ring-fused indol-1-yl group contains two or more heterocyclic rings. For example, the fused ring may contain two or three heterocyclic rings.

[0031] In this specification, an example of an aromatic hydrocarbon ring is a benzene ring. Examples of aromatic heterocycles include a furan ring, a thiophene ring, a pyrrole ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, a pyrrole ring, a pyrazole ring, and an imidazole ring. Examples of aliphatic hydrocarbon rings include a cyclopentane ring, a cyclohexane ring, and a cycloheptane ring. Examples of aliphatic heterocycles include a piperidine ring, a pyrrolidine ring, and an imidazoline ring. Specific examples of fused rings include a naphthalene ring, an anthracene ring, a phenanthrene ring, a pyran ring, a tetracene ring, an indole ring, an isoindole ring, a benzimidazole ring, a benzotriazole ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, a quinoxaline ring, and a cinnoline ring.

[0032] In a preferred embodiment of the present invention, the ring-fused indol-1-yl group is a benzofuran-fused indol-1-yl group, a benzothiophene-fused indol-1-yl group, an indole-fused indol-1-yl group, or a silaindene-fused indol-1-yl group. In a more preferred embodiment of the present invention, the indol-1-yl group is a benzofuran-fused indol-1-yl group, a benzothiophene-fused indol-1-yl group, or an indole-fused indol-1-yl group.

[0033] In the present invention, a substituted or unsubstituted benzofuro[2,3-e]indol-1-yl group can be used as the benzofuran-fused indol-1-yl group. A substituted or unsubstituted benzofuro[3,2-e]indol-1-yl group can also be used. A substituted or unsubstituted benzofuro[2,3-f]indol-1-yl group can also be used. A substituted or unsubstituted benzofuro[3,2-f]indol-1-yl group can also be used. A substituted or unsubstituted benzofuro[2,3-g]indol-1-yl group can also be used. A substituted or unsubstituted benzofuro[3,2-g]indol-1-yl group can also be used. The fused rings constituting these groups may or may not be fused with further rings. In the present invention, a substituted or unsubstituted benzofuro[2,3-a]carbazol-9-yl group can be used as the benzofuran-fused indol-1-yl group. A substituted or unsubstituted benzofuro[3,2-a]carbazol-9-yl group can also be used. A substituted or unsubstituted benzofuro[2,3-b]carbazol-9-yl group can also be used. A substituted or unsubstituted benzofuro[3,2-b]carbazol-9-yl group can also be used. A substituted or unsubstituted benzofuro[2,3-c]carbazol-9-yl group can also be used. A substituted or unsubstituted benzofuro[3,2-c]carbazol-9-yl group can also be used. The fused rings constituting these groups may or may not be fused with further rings. Preferred benzofuran-fused indol-1-yl groups include groups having any of the structures shown below, in which the hydrogen atoms may or may not be substituted. For example, preferred examples include groups substituted with an aryl group such as a phenyl group, or groups substituted at the 3-position of the carbazole ring. Furthermore, the benzene ring in the structure shown below may or may not be fused with a further ring. The wavy line indicates the bonding position. [ka]

[0034] A carbazol-9-yl group in which two benzofuran rings are fused at the 2- and 3-positions can also be used. Specifically, it is a group having any of the structures shown below, in which the hydrogen atoms in the structures shown below may or may not be substituted. Furthermore, the benzene ring in the structures shown below may or may not be fused with a further ring. [ka]

[0035] In the present invention, a substituted or unsubstituted benzothieno[2,3-e]indol-1-yl group can be used as the benzothiophene-fused indol-1-yl group. A substituted or unsubstituted benzothieno[3,2-e]indol-1-yl group can also be used. A substituted or unsubstituted benzothieno[2,3-f]indol-1-yl group can also be used. A substituted or unsubstituted benzothieno[3,2-f]indol-1-yl group can also be used. A substituted or unsubstituted benzothieno[2,3-g]indol-1-yl group can also be used. A substituted or unsubstituted benzothieno[3,2-g]indol-1-yl group can also be used. The fused rings constituting these groups may or may not be fused with further rings. In the present invention, a substituted or unsubstituted benzothieno[2,3-a]carbazol-9-yl group can be used as the benzothiophene-fused indol-1-yl group. A substituted or unsubstituted benzothieno[3,2-a]carbazol-9-yl group can also be used. A substituted or unsubstituted benzothieno[2,3-b]carbazol-9-yl group can also be used. A substituted or unsubstituted benzothieno[3,2-b]carbazol-9-yl group can also be used. A substituted or unsubstituted benzothieno[2,3-c]carbazol-9-yl group can also be used. A substituted or unsubstituted benzothieno[3,2-c]carbazol-9-yl group can also be used. The fused rings constituting these groups may or may not be fused with further rings. Preferred benzothiophene-fused indol-1-yl groups include groups having any of the following structures, in which the hydrogen atoms may or may not be substituted. For example, preferred examples include groups substituted with an aryl group such as a phenyl group, or groups substituted at the 3-position of the carbazole ring. Furthermore, the benzene ring in the following structure may or may not be fused with a further ring. [ka]

[0036] A carbazol-9-yl group in which two benzothiophene rings are fused at the 2- and 3-positions can also be used. Specifically, it is a group having any of the structures shown below, in which the hydrogen atoms may or may not be substituted. Furthermore, the benzene ring in the structure shown below may or may not be fused with a further ring. [ka]

[0037] In the present invention, a substituted or unsubstituted indolo[2,3-e]indol-1-yl group can be used as the indole-fused indol-1-yl group. A substituted or unsubstituted indolo[3,2-e]indol-1-yl group can also be used. A substituted or unsubstituted indolo[2,3-f]indol-1-yl group can also be used. A substituted or unsubstituted indolo[3,2-f]indol-1-yl group can also be used. A substituted or unsubstituted indolo[2,3-g]indol-1-yl group can also be used. A substituted or unsubstituted indolo[3,2-g]indol-1-yl group can also be used. The fused rings constituting these groups may or may not be fused with further rings. In the present invention, a substituted or unsubstituted indolo[2,3-a]carbazol-9-yl group can be used as the indole-fused indol-1-yl group. A substituted or unsubstituted indolo[3,2-a]carbazol-9-yl group can also be used. A substituted or unsubstituted indolo[2,3-b]carbazol-9-yl group can also be used. A substituted or unsubstituted indolo[3,2-b]carbazol-9-yl group can also be used. A substituted or unsubstituted indolo[2,3-c]carbazol-9-yl group can also be used. A substituted or unsubstituted indolo[3,2-c]carbazol-9-yl group can also be used. The fused rings constituting these groups may or may not be fused with further rings. Preferred indole-fused indol-1-yl groups include groups having any of the following structures, in which the hydrogen atoms may or may not be substituted. For example, preferred examples include groups substituted with an aryl group such as a phenyl group, or groups substituted at the 3-position of the carbazole ring. Furthermore, the benzene ring in the following structure may or may not be fused with a further ring. [ka]

[0038] In a preferred embodiment of the present invention, the benzofuran-fused indol-1-yl group, the benzothiophene-fused indol-1-yl group, the indole-fused indol-1-yl group, and the silaindene-fused indol-1-yl group are substituted with a substituted or unsubstituted aryl group. Preferably, they are substituted with a substituted or unsubstituted phenyl group. The substituents of the aryl group and the phenyl group referred to here can be selected from any of Substituent Groups A to E, and are preferably selected from Substituent Group E. It is also preferred that the aryl group and the phenyl group referred to here are unsubstituted. In a preferred embodiment of the present invention, the ring-fused indol-1-yl group is a benzofuran-fused indol-1-yl group substituted with a substituted or unsubstituted aryl group.

[0039] Specific examples of IDL groups that can be employed in general formula (1) are shown below. However, the IDL 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, D represents a deuterium atom, and * indicates a bonding position. Methyl groups are not shown. Therefore, for example, D199 represents a 3-methylcarbazol-9-yl group.

[0040] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0041] R in general formula (1) 1 ~R 5 Among these, those which are not cyano groups, substituted or unsubstituted aryl groups, substituted or unsubstituted pyridyl groups, or IDL groups (hereinafter referred to as "the remaining R 1 ~R 5 ") is a hydrogen atom, a deuterium atom, or a substituent that is not a cyano group, an aryl group, a pyridyl group, or an IDL group (hereinafter referred to as the "remaining substituents"). Remaining R 1 ~R 5 may all be hydrogen atoms or deuterium atoms, for example, all may be hydrogen atoms, or for example, all may be deuterium atoms. 1 ~R 5 Among these, the number of remaining substituents is 0 to 3, and may be, for example, 2 or 3, or 0 or 1. The remaining substituents may be selected from the following substituent group A, may be selected from the following substituent group B, may be selected from the following substituent group C, may be selected from the following substituent group D, or may be selected from the following substituent group E. In one embodiment of the present invention, the remaining substituents include a donor group. In one embodiment of the present invention, all of the remaining substituents are donor groups. In particular, when the number of remaining substituents is three, at least one is a donor group. The donor group referred to here can be selected from groups with a negative Hammett σp value. The Hammett σp value was proposed by L.P. Hammett, and quantifies the effect of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, 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). In one embodiment of the present invention, all of the remaining substituents are unsubstituted ring-fused indol-1-yl groups. In one embodiment of the present invention, all of the remaining substituents are unsubstituted carbazol-9-yl groups. The unsubstituted carbazol-9-yl groups referred to here may be unsubstituted ring-fused carbazol-9-yl groups. In one embodiment of the present invention, R 1 ~R 5 In one embodiment of the present invention, at least one of R is a substituted fused carbazol-9-yl group and at least one is an unsubstituted fused carbazol-9-yl group. 1 ~R 5 at least two of R are substituted fused carbazol-9-yl groups; 1 ~R 5 In one embodiment of the present invention, at least one of R 1 ~R5 at least one of R is a substituted fused carbazol-9-yl group; 1 ~R 5 At least two of R are unsubstituted fused carbazol-9-yl groups. 1 ~R 5 two of R are substituted fused carbazol-9-yl groups; 1 ~R 5 Two of these are unsubstituted fused carbazol-9-yl groups. In one aspect of the present invention, R 1 ~R 5 are each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted ring-fused indol-1-yl group. For example, R 1 and R 5 is an unsubstituted ring-fused indol-1-yl group, and R 2 a ring-fused indol-1-yl group substituted with R 4 is a substituted or unsubstituted ring-fused indol-1-yl group, and R 3 is a substituted or unsubstituted aryl group. For example, R 1 and R 5 is an unsubstituted ring-fused indol-1-yl group, and R 2 and R 4 a ring-fused indol-1-yl group substituted with R 3 is a substituted or unsubstituted aryl group. 1 ~R 5 are each independently a substituted or unsubstituted aryl group or a substituted ring-fused indol-1-yl group.

[0042] In one aspect of the present invention, R in general formula (1) 1 ~R 5 Three to five of the R 1 ~R 5 represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. 1 ~R 5In one embodiment of the present invention, at least one of the donor groups represented by R in general formula (1) is a fused carbazolyl group. 1 ~R 5 Three or four of the R 1 ~R 5 One or two of the R 1 ~R 5 is a hydrogen atom or a deuterium atom. Preferably, some or all of the donor groups are substituted or unsubstituted carbazol-9-yl groups. In one embodiment of the present invention, donor groups with different structures are present among the 3 to 4 donor groups. For example, substituted or unsubstituted ring-fused indol-1-yl groups with different structures are present. For example, a substituted ring-fused indol-1-yl group and an unsubstituted ring-fused indol-1-yl group are present. More specifically, carbazol-9-yl groups with different substitution states are present, and specifically, a case where a substituted carbazolyl group and an unsubstituted carbazolyl group are present together can be exemplified. For example, R 1 and R 2 are donor groups of the same structure, and R 4 and R 5 But R 1 and R 2 Alternatively, the three or four donor groups may all have the same structure. In a preferred embodiment of the present invention, R 3 is an aryl group or a pyridyl group. 1 ~R 5 The donor group R can take has a structure represented by the following general formula (4): 21 and R 22 R each independently represents 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. 21 and R 22 may be bonded to each other to form a cyclic structure. L represents a single bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group. * represents the bonding position to the carbon atom (C) constituting the ring skeleton of the ring in general formula (1). [ka]

[0043] In general formula (1), R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 may be bonded to each other to form a cyclic structure. For the explanation and specific examples of the cyclic structure here, the explanation and specific examples of the fused rings in the explanation of "ring fusion" above can be referred to. In one aspect of the present invention, R 1 and R 2 , R 4 and R 5 In one embodiment of the present invention, at least one pair of R 2 and R 3 , R 3 and R 4 In one embodiment of the present invention, at least one pair of R 1 and R 2 , R 4 and R 5 In one embodiment of the present invention, R 2 and R 3 , R 3 and R 4 In one embodiment of the present invention, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 are not bonded to each other to form a ring structure.

[0044] 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. For example, the compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon, deuterium, nitrogen, oxygen, and sulfur atoms. In one embodiment of the present invention, the compound represented by general formula (1) has a symmetric structure. For example, it may have a linear symmetric structure. When it has a linear symmetric structure, R in general formula (1) 1 and R 5 is the same as R 2 and R 4 In one embodiment of the present invention, the compound represented by general formula (1) has an asymmetric structure.

[0045] In the present specification, "substituent group A" refers to a hydroxyl group, a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (for example, having 1 to 40 carbon atoms), an alkoxy group (for example, having 1 to 40 carbon atoms), an alkylthio group (for example, having 1 to 40 carbon atoms), an aryl group (for example, having 6 to 30 carbon atoms), an aryloxy group (for example, having 6 to 30 carbon atoms), an arylthio group (for example, having 6 to 30 carbon atoms), a heteroaryl group (for example, having 5 to 30 ring skeleton atoms), a heteroaryloxy group (for example, having 5 to 30 ring skeleton atoms), a heteroaryl group, ... It means one group or a combination of two or more groups 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 group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 40 carbon atoms), alkoxy groups (e.g., having 1 to 40 carbon atoms), aryl groups (e.g., having 6 to 30 carbon atoms), aryloxy groups (e.g., having 6 to 30 carbon atoms), heteroaryl groups (e.g., having 5 to 30 ring skeleton atoms), heteroaryloxy groups (e.g., having 5 to 30 ring skeleton atoms), and diarylaminoamino groups (e.g., having 0 to 20 carbon atoms). In this specification, the term "substituent group C" refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups (e.g., having 6 to 22 carbon atoms), heteroaryl groups (e.g., having 5 to 20 ring skeleton atoms), and diarylamino groups (e.g., having 12 to 20 carbon atoms). In this specification, the term "substituent group D" refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups (e.g., having 6 to 22 carbon atoms), and heteroaryl groups (e.g., having 5 to 20 ring skeleton atoms). In this specification, the term "substituent group E" refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (for example, having 1 to 20 carbon atoms) and aryl groups (for example, having 6 to 22 carbon atoms). In the present specification, when a "substituent" or "substituted or unsubstituted" is used, the substituent may be selected from, for example, Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E.

[0046] Specific examples of the compound represented by general formula (1) are shown in the following Tables 1 and 2. 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 general formula (1) 1 ~R 5 The structures of compounds 1 to 184 are shown individually by specifying each compound. In Table 2, each row contains the R 1 ~R 5 By displaying these together, the structures of compounds 1 to 6748200 are shown. For example, in the column of compounds 1 to 184 in Table 2, R 3 is fixed to Ar1 (phenyl group), and R 1 and R 5 is fixed to D204 (carbazol-9-yl group), and R 2 and R 4 The compounds D1 to D184 are designated as compounds 1 to 184, respectively. 2 and R 4 In other words, the column of compounds 1 to 184 in Table 2 collectively displays compounds 1 to 184 identified in Table 1. Similarly, in the column of compounds 185 to 37536 in Table 2, R 3 is fixed to Ar1 (phenyl group), and R 1 and R 5 are the same and are D1 to D203, and R 2 and R 4are the same and are D1 to D184. Of the non-fixed groups, R takes D1 to D203. 1 and R 5 First fix D1 to D184 and then R 2 and R 4 are rearranged in order and compound numbers are assigned. 1 and R 5 is D1 and R 2 and R 4 The compounds D1 to D184 are compounds 185 to 368, respectively, and R 1 and R 5 is D2 and R 2 and R 4 The compounds D1 to D184 are compounds 369 to 552, respectively, and R 1 and R 5 is D3 and R 2 and R 4 The compounds are numbered in the order D1 to D184, and R 1 and R 5 is D203 and R 2 and R 4 The compounds D1 to D184 are, in order, compounds 37353 to 37536. Compounds 37537 to 6748200 in Table 2 are also identified in the same manner. [Table 1] [Table 2-1] [Table 2-2] [Table 2-3] [Table 2-4] [Table 2-5] [Table 2-6]

[0047] Compounds 1(D) to 6412032(D) are compounds in which all hydrogen atoms present in the molecules of the above compounds 1 to 6412032 have been replaced with deuterium atoms. In addition, when rotamers exist among the above specific compound examples, the mixture of rotamers and each separated rotamer are also considered to be disclosed in the present specification.

[0048] In a preferred embodiment of the present invention, the compound represented by general formula (1) is selected from the following group of compounds: [ka] [ka]

[0049] In one aspect of the present invention, R in general formula (1) 2 and R is a ring-fused indol-1-yl group (the number of rings constituting the fused ring is 4 or more) substituted only with 1 , R 4 , R 5 is another donor group. In a preferred embodiment of the present invention, the compound represented by general formula (1) is selected from the following group of compounds: [ka] [ka]

[0050] 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.

[0051] 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.

[0052] 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]

[0053] 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.

[0054] Specific structural examples of the repeating unit include structures represented by the following formulas. [ka]

[0055] 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]

[0056] 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.

[0057] 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 one 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 one 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 one embodiment of the present disclosure, a CMOS (complementary metal-oxide semiconductor) can be fabricated using a compound represented by general formula (1).

[0058] 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.

[0059] [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. For example, a cyanobenzene having an alkyl group and a halogen atom can be reacted with a substituted or unsubstituted carbazole to synthesize a compound of general formula (1) substituted with a substituted or unsubstituted carbazole-9-yl group. For details of the reaction conditions, please refer to the synthesis examples described below.

[0060] [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).

[0061] [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.

[0062] [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. An example of an organic electroluminescent device is shown in Figure 1.

[0063] 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.

[0064] 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.

[0065] [ka] [ka] [ka]

[0066] 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 the assist dopant having the structure represented by general formula (1).

[0067] 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.

[0068] In some embodiments, the host material is selected from the group consisting of: [ka] [ka] In one embodiment, the light-emitting layer contains two or more types of TADF molecules with different structures. For example, the light-emitting layer may contain three materials, the host material, the first TADF molecule, and the second TADF molecule, whose excited singlet energy levels are in the order of highest to lowest. 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.

[0069] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0070] 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.

[0071] 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.

[0072] 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.

[0073] 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.

[0074] [ka]

[0075] Next, preferred examples of compounds that can be used as the electron injection material will be listed. [ka]

[0076] 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.

[0077] 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.

[0078] [ka]

[0079] 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.

[0080] [ka]

[0081] 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.

[0082] 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.

[0083] [ka]

[0084] 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.

[0085] [ka]

[0086] 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.

[0087] [ka]

[0088] 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.

[0089] 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).

[0090] 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.

[0091] 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.

[0092] 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.

[0093] 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.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] 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.

[0098] 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]

[0099] 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.

[0100] (Synthesis Example 1) [ka]

[0101] compound 1 Compound A (0.75 g, 1.47 mmol) was added to a dimethylformamide solution (30 mL) of 2-phenyl-5H-benzofuro[3,2-c]carbazole (1.08 g, 2.2 mmol) and potassium carbonate (0.6 g, 3.0 mmol) under a nitrogen atmosphere, and the mixture was stirred at 110°C for 18 hours. The mixture was then cooled to room temperature and quenched by adding methanol. The precipitated solid was filtered and washed with water and methanol. The resulting solid was purified by silica gel column chromatography to give compound 1 (1.29 g, 1.1 mmol, 74.5% yield). 1H NMR (400 MHz, CDCl3) δ 8.24 (s, 2H), 7.90 (d, J= 7.6 Hz, 2H), 7.77-7.55 (m, 12H), 7.52-7.48 (m, 4H), 7.47-7.26 (m, 12H), 7.21-7.03 (m,10H), 7.00 (t, J = 5.4, 5.6 Hz,2H), 6.75 (d, J = 7.6 Hz, 2H), 6.44-6.36 (m, 3H) ASAP mass spectrometry: theoretical 1171.39, observed 1172.6

[0102] compound 2 Compound A (0.87 g, 2.5 mmol) was added to a dimethylformamide solution (23 mL) of 2-phenyl-5H-[1]benzothieno[3,2-c]carbazole (0.65 g, 1.19 mmol) and potassium carbonate (0.41 g, 2.98 mmol) under a nitrogen atmosphere, and the mixture was stirred at 60 °C for 17 hours. The mixture was then cooled to room temperature and quenched with methanol. The precipitated solid was filtered and washed with water and methanol. The resulting solid was purified by silica gel column chromatography to give compound 2 (1.08 g, 0.92 mmol, 77.1% yield). 1 H NMR (400 MHz, Chloroform-D) 8.64 (s, H), 8.08-8.03 (m, 2H), 7.98 (d, J = 8.4 Hz, H), 7.89 (t, J = 7.2,5.6 Hz, H), 7.85 (d, J = 8.8 Hz, H), 7.60ppm (d, J = 6.8 Hz, 2H), 7.55 (d, J = 6.8 Hz, 2H),7.51-7.11 (m, 15H), 6.827-6.75 (m, 2H), 6.71 (t, J = 7.2, 8.0Hz, 2H), 6.69-6.61 (m, J = 7.6, 7.6Hz,H), 6.52 (t, J = 7.2, 8.4 Hz,H), 6.44 (t, J = 8.4, 7.2 Hz,H) ASAP mass spectrometry: theoretical 1203.34, observed 1172.52

[0103] compound 11 Compound A (0.76 g, 1.40 mmol) was added to a solution of 9-phenyl-12H-benzofuro[3,2-a]carbazole (1.07 g, 3.22 mmol) and potassium carbonate (0.58 g, 4.20 mmol) in N,N-dimethylformamide (14.0 mL) under a nitrogen stream, and the mixture was stirred at 150 °C for 12 hours. The reaction mixture was returned to room temperature, water was added, and the precipitate was filtered off. The residue was washed with methanol and dried under vacuum. The crude product was purified by silica gel column chromatography (hexane:toluene:chloroform = 3.5:6.0:0.5) to obtain compound 11 (1.00 g, 0.85 mmol, 76% yield) as a pale yellow solid. 1 H-NMR (400 MHz, CDCl3): 7.97-7.95 (broad, 2H), 7.84-7.82 (m, 6H), 7.75-7.73 (m, 6H), 7.63 (d, J = 8.2 Hz, 2H), 7.57-7.52 (m, 9H), 7.49-7.41 (m, 4H), 7.16 (d, J = 8.2 Hz, 2H), 7.08 (t, J = 8.2 Hz, 2H), 6.85-6.90 (m, 8H), 6.66 (d, J = 8.2 Hz, 2H), 6.54 (t, J= 8.2 Hz, 2H), 6.47 (t, J = 8.2 Hz, 2H), 6.39 (d, J = 8.2 Hz, 2H). ASAP MS Spectral Analysis: C 85 H 49 N5O2: Calculated 1171.39, Observed 1172.80

[0104] compound 13 Compound A (0.8 g, 1.5 mmol) was added to a dimethylformamide solution (15 mL) of 9-phenyl-5H-benzofuro[3,2-c]carbazole (1.00 g, 3.0 mmol) and potassium carbonate (0.51 g, 3.7 mmol) under a nitrogen atmosphere, and the mixture was stirred overnight at 70 °C. The mixture was returned to room temperature and quenched by adding water. The precipitated solid was filtered and washed with methanol. The resulting solid was purified by silica gel column chromatography to give compound 13 (1.6 g, 1.4 mmol, 93% yield). 1 H NMR (400 MHz, CDCl3) δ 8.04 (s, 2H), 8.02 (d, J = 7.2 Hz, 2H), 7.71 (dd, J = 7.6, 3.2 Hz, 4H), 7.67 (d, J = 8.0 Hz, 4H), 7.62 (d, J = 5.6 Hz, 2H), 7.58 (d, J = 9.6 Hz, 2H), 7.473 (t, J = 8.0 Hz, 4H), 7.37 (t, J = 6.8 Hz, 2H),7.33 (d, J=6.0 H, 2H), 7.31 (d, J = 6.0 Hz, 2H), 7.18-7.08 (m, 18H), 6.67 (d, J = 7.2 Hz, 2H), 6.43 (t, J = 7.6 Hz,1H), 6.33 (t, J = 7.6 Hz, 2H). ASAP mass spectrometry: theoretical 1172.89, observed 1172.68.

[0105] compound 14 Compound A (1.0 g, 1.8 mmol) was added to a solution of 9-phenyl-5H-[1]benzofurothieno[3,2-c]carbazole (1.4 g, 4.0 mmol) and potassium carbonate (0.76 g, 5.5 mmol) in dimethylformamide (36 mL) under a nitrogen atmosphere and stirred at 100°C for 2 hours. The mixture was then cooled to room temperature and quenched with methanol. The precipitated solid was filtered and washed with water and methanol. The resulting solid was purified by silica gel column chromatography to give compound 14 (1.8 g, 1.5 mmol, 82% yield). 1 H NMR (400 MHz, DMSO) δ 8.68 (d, J = 1.6 Hz, 2H), 8.36 (d, J= 8.8 Hz, 2H), 8.21-8.01 (m, 10H), 7.87-7.85 (m, 8H), 7.75 (dd, J=1.6, 8.4 Hz, 2H), 7.67 (d, J = 7.6 Hz, 2H), 7.54 (t, J = 7.6 Hz, 4H), 7.42 (t, J = 7.6 Hz, 2H),7.30-7.20 (m, 6H), 7.18-7.04 (m, 6H), 6.91-6.71 (m, 2H), 6.37-6.24 (m, 3H) ASAP mass spectrometry: theoretical 1205.49, observed 1205.63

[0106] compound 27 Compound A (0.5 g, 0.92 mmol) was added to a dimethylformamide solution (18 mL) of 11-phenyl-5H-benzofuro[3,2-c]carbazole (0.80 g, 1.47 mmol) and potassium carbonate (0.51 g, 3.68 mmol) under a nitrogen atmosphere, and the mixture was stirred at 100°C for 4 hours. The mixture was then cooled to room temperature and quenched with methanol. The precipitated solid was filtered and washed with water and methanol. The resulting solid was purified by silica gel column chromatography to give compound 27 (1.21 g, 1.03 mmol, 70.0% yield). 1 H NMR (400 MHz, Chloroform-D) 7.95 (d, J = 6.8 Hz, 4H), 7.89 (d, J = 6.8 Hz, 2H), 7.83 (d, J = 8.0 Hz, 2H), 7.70 (d, J= 7.6 Hz, 2H), 7.57-7.51 (m, 4H), 7.43-7.38 (m, 8H), 7.38-7.29 (m,4H) , 7.17-7.01 (m, 24H), 6.64 (d, J = 7.2Hz, 2H), 6.40 (t, J = 7.6, 7.6 Hz,H) , 6.31 (t, J = 7.6, 7.2 Hz,2H), ASAP mass spectrometry: theoretical 1171.39, observed 1172.7

[0107] compound 91 Compound A (0.5 g, 0.92 mmol) was added to a dimethylformamide solution (18 mL) of 3-phenyl-5H-benzofuro[3,2-c]carbazole (0.67 g, 2.0 mmol) and potassium carbonate (0.32 g, 2.29 mmol) under a nitrogen atmosphere, and the mixture was stirred at 80 °C for 14 hours. The mixture was then cooled to room temperature and quenched with methanol. The precipitated solid was filtered and washed with water and methanol. The resulting solid was purified by silica gel column chromatography to give compound 91 (0.82 g, 0.7 mmol, 76.9% yield). 1 H NMR (400 MHz, CDCl3) 8.09 (d, J = 8.0 Hz, 2H), 7.84 (t, J = 7.6, 7.6 Hz,4H), 7.7ppm (d, J = 7.6 Hz, 2H), 7.69 (d, J = 8.4 Hz, 4H),7.51-6.99 (m, 29H), 6.947 (t, J = 7.2, 7.2 Hz,2H), 6.84 (t, J = 7.2, 7.6 Hz,2H), 6.61 (d, J = 7.2 Hz, 2H), 6.36-6.28 (m, 2H) ASAP mass spectrometry: Calculated 1171.39, Observed 1173.61

[0108] (Synthesis Example 2) [ka]

[0109] Compound 6035845 Under a nitrogen atmosphere, compound B (1.5 g, 2.7 mmol), 2-phenyl-d5-5H-benzofuro[3,2-c]carbazole (1.9 g, 5.6 mmol), and potassium carbonate (1.1 g, 8.1 mmol) were added to dimethylformamide (54 mL) and stirred at 80°C for 15 hours. The mixture was returned to room temperature, water was added, and the precipitated solid was filtered. The obtained solid was subjected to silica gel column chromatography and reprecipitation to obtain compound 6035845 (3.2 g, 2.6 mmol, 98% yield). 1 H NMR (400 MHz, CDCl3) δ 8.21 (s, 2H), 7.88 (d, J= 1.9 Hz, 2H), 7.76-7.64 (m, 4H), 7.64-7.53 (m,48H), 7.46-7.30 (m, 7H), 7.30-7.20 (m, 4H), 7.20-6.91 (m, 11H), ASAP mass spectrometry: theoretical 1187.45, observed 1188.06

[0110] (Synthesis Example 3) [ka]

[0111] Compound 6298418 Under a nitrogen stream, compound C (1.1 g, 1.58 mmol), 2-phenyl-d5-5H-benzofuro[3,2-c]carbazole (0.59 g, 1.73 mmol), and potassium carbonate (0.43 g, 3.15 mmol) were added to dimethylformamide (15 mL) and stirred at 80 °C for 15 hours. The mixture was returned to room temperature, water was added, and the precipitated solid was filtered. The obtained solid was subjected to silica gel column chromatography and reprecipitation to obtain compound 6298413 (1.5 g, 1.5 mmol, 93% yield). 1H NMR (400 MHz, CDCl3) δ 8.19 (s, 1H), 7.87 (d, J= 1.9 Hz, 1H), 7.75-7.51 (m, 8H), 7.40-7.29 (m, 4H), 7.25-7.02 (m, 13H), 6.99-6.93 (m, 6H) ASAP mass spectrometry: theoretical 1016.34, observed 1016.70

[0112] (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 1 and H1 were evaporated from different evaporation sources under conditions of less than Pa, to form a thin film with a thickness of 100 nm and a concentration of Compound 1 of 20 wt %. Instead of Compound 1, Compounds 2, 11, 13, 14, 27, 91, 6035845, 6298413, and Comparative Compound 1 were used to prepare thin films in the same manner. The maximum emission wavelength (λmax) and photoluminescence quantum yield (PLQY) were measured when each thin film was irradiated with 300 nm excitation light. The HOMO and LUMO energies were also measured. The results are shown in Table 3.

[0113] [Table 3] [ka]

[0114] (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 laminated using a Pa. First, HAT-CN was formed on ITO to a thickness of 10 nm, NPD was formed on top of that to a thickness of 35 nm, and PTCz was further formed on top of that to a thickness of 10 nm. Next, H1 and compound 1 were co-evaporated from different evaporation sources to form a 40 nm thick layer, which served as the light-emitting layer. The concentration of compound 1 in the light-emitting layer was 30 wt%. Next, ET1 was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-evaporated from different evaporation sources to form a 20 nm thick layer. The concentrations of Liq and SF3-TRZ in this layer were 30 wt% and 70 wt%, respectively. Liq was then formed to a thickness of 2 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form a cathode, completing the organic electroluminescence device. Instead of Compound 1, Compounds 2, 11, 13, 14, 27, 91, 6035845, and Comparative Compound 1 were used to prepare organic electroluminescence devices in the same manner. The maximum external quantum efficiency (EQE) of each organic electroluminescence device using compounds 1, 2, 11, 13, 14, 27, 91, and 6035845 was measured and showed a high value of 21 to 26%. In addition, the delayed fluorescence lifetime τ2 of each organic electroluminescence device using compounds 1, 2, 11, 13, 27, and 6035845 was measured and found to be 2.2 to 2.9 μsec, which was shorter than the delayed fluorescence lifetime τ2 (3.5 μsec) of the organic electroluminescence device using comparative compound 1.

[0115] In addition, for the organic electroluminescence device using Compound 1, 5.5 mA / cm 2 The time (LT95) until the luminescence intensity reached 95% of the initial value was measured, and it was confirmed that this was 1.95 times longer than that of an organic electroluminescence element using comparative compound 1. Furthermore, the degree of orientation of a thin film in which compound 1 was doped in H1 at 30 mass % was -0.43, confirming that the orientation was high.

[0116] The compound represented by general formula (1) has high luminous efficiency, short delayed fluorescence lifetime, and excellent alignment. Furthermore, an organic electroluminescence device using the compound represented by general formula (1) has high luminous efficiency, long lifetime, and excellent durability. [ka] [Explanation of symbols]

[0117] 1 Base material 2 Anode 3. Hole injection layer 4. Hole transport layer 5. Light-emitting layer 6 Electron transport layer 7 Cathode

Claims

1. A compound represented by the following general formula (1): 【Chemical 1】 In the general formula (1), R 3 is a substituted or unsubstituted aryl group. １ , R 2 , R 4 and R ５ Among these, two or three are unsubstituted carbazol-9-yl groups, and the remaining one or two are each independently substituted with an aryl group and formed by condensing rings having one or more atoms selected from the group consisting of oxygen atoms and sulfur atoms as ring skeleton-constituting atoms (the number of rings constituting the condensed rings is four or more).

2. R １ and R ５ is an unsubstituted carbazol-9-yl group, and R ２ and R ４ are each independently substituted with an aryl group and are a carbazol-9-yl group fused with a ring having one or more atoms selected from the group consisting of an oxygen atom and a sulfur atom as ring skeleton-constituting atoms (the number of rings constituting the fused ring is four or more).

3. The compound according to claim 1 or 2, which has an axisymmetric structure.

4. A light-emitting material comprising the compound according to any one of claims 1 to 3.

5. A delayed fluorescent material comprising the compound according to any one of claims 1 to 3.

6. A film comprising the compound according to any one of claims 1 to 3.

7. An organic semiconductor device comprising the compound according to any one of claims 1 to 3.

8. An organic light-emitting device comprising the compound according to any one of claims 1 to 3.

9. The organic light-emitting device of claim 8 , wherein the device has a layer comprising the compound, the layer also comprising a host material.

10. 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.

11. The organic light-emitting device of claim 9 , 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.

12. 12. The organic light-emitting device according to claim 9, wherein the compound emits the greatest amount of light among materials contained in the device.

13. The organic light-emitting device according to claim 11 , wherein the amount of light emitted from the light-emitting material is greater than the amount of light emitted from the compound.

14. The organic light-emitting device according to any one of claims 8 to 13, which is an organic electroluminescence device.

15. The organic light-emitting device according to any one of claims 8 to 13, which emits fluorescence or delayed fluorescence.

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