Compound, light-emitting material and light-emitting element

Abstract

This organic light-emitting element in which a compound represented by the general formula is used exhibits excellent light-emitting characteristics. In the general formula, one or two of R1-R4 are fused-ring carabazol-9-yl groups, at least one of which is a fused-ring carbazol-9-yl group substituted by 2 or more aryl groups; and two or three of R1-R4 are non-fused-ring carbazol-9-yl groups.

Description

Compound, light-emitting material and light-emitting device

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

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

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

[0004] Since this principle was clarified, various delayed fluorescent materials have been discovered through extensive research, including the following compound in which two cyano groups and four substituted or unsubstituted carbazol-9-yl groups are substituted on a benzene ring (Patent Document 1).

[0005]

[0006] WO2020 / 0022378

[0007] Even if a material emits delayed fluorescence, one with extremely good properties and no practical problems has not yet been provided. Therefore, it would be even more useful if a delayed fluorescence material with even better luminescence properties could be provided than the delayed fluorescence material proposed in Patent Document 1, for example. However, the improvement of delayed fluorescence materials is 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.

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

[0010] [1] A compound represented by the following general formula (1): [In general formula (1), R １ and R ２ ~R ４ 0 to 1 of R each independently represent a substituted or unsubstituted fused ring carbazol-9-yl group, and at least R １ is a fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are substituted on the carbon atoms constituting the ring skeleton. ２ ~R ４ each independently represents a substituted or unsubstituted non-fused carbazol-9-yl group.] [2] R ２ ~R ４ [3] The compound according to [1], wherein when one of R is a fused carbazol-9-yl group, the carbon atoms constituting the ring skeleton of the fused carbazol-9-yl group are substituted with two or more substituted or unsubstituted aryl groups. １ represents a fused carbazol-9-yl group having two or more substituted or unsubstituted aryl groups substituted on the carbon atoms constituting the ring skeleton, and R ２~R ４ are each independently a substituted or unsubstituted non-fused carbazol-9-yl group. [4] The compound according to any one of [1] to [3], wherein the fused carbazol-9-yl group having two or more substituted or unsubstituted aryl groups substituted on the carbon atoms constituting the ring skeleton has a fused ring structure of 5 to 7 rings including the carbazole. [5] The compound according to any one of [1] to [4], wherein the fused carbazol-9-yl group having two or more substituted or unsubstituted aryl groups substituted on the carbon atoms constituting the ring skeleton has a structure represented by the following general formula (2): [In the general formula (2), X is O, S, N(R ８ ) or C(R ９ ) (R １０ ) represents. ５ ~R ７ each independently represents a substituent (the substituent includes a deuterium atom); n5 and n7 each independently represent an integer of 0 to 4, and n6 represents an integer of 0 to 2. However, n5 + n6 + n7 is an integer of 2 to 10, and the number of R ５ ~R ７ At least two of R bonded to adjacent carbon atoms constituting the ring skeleton are substituted or unsubstituted aryl groups. ５ R bonded to adjacent ring skeleton carbon atoms ６ R bonded to adjacent ring skeleton carbon atoms ７ may be bonded to each other to form a cyclic structure. * represents the bonding position to the benzene ring in general formula (1).] [6] The compound according to [5], wherein n5 + n6 + n7 is 2. [7] R ５ One of and R ７ are each independently a substituted or unsubstituted aryl group, or ５ One of and R ６ are each independently a substituted or unsubstituted aryl group, or ６ One of and R ７[8] The compound according to any one of [1] to [7], wherein the substituted or unsubstituted non-fused carbazol-9-yl group has a structure represented by the following general formula (3): [In the general formula (3), R １１ and R １２each independently represents a substituent (the substituent also includes a deuterium atom). n11 and n12 each independently represent an integer of 0 to 4. One of the carbon atoms constituting the ring skeleton at positions 1 to 4 of the carbazole may be substituted with a nitrogen atom, and one of the carbon atoms constituting the ring skeleton at positions 5 to 8 of the carbazole may be substituted with a nitrogen atom. * represents the bonding position to the benzene ring in general formula (1).] [9] A composition comprising the compound according to any one of [1] to [8] and a pyrromethene boron complex compound.

[10] A light-emitting material comprising the compound according to any one of [1] to [8].

[11] A delayed fluorescent material comprising the compound according to any one of [1] to [8].

[12] A film comprising the compound according to any one of [1] to [8] or the composition according to [9].

[13] An organic semiconductor device comprising the compound according to any one of [1] to [8] or the composition according to [9].

[14] An organic light-emitting device comprising the compound according to any one of [1] to [8] or the composition according to [9].

[15] The organic light-emitting device according to

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

[16] The organic light-emitting device according to

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

[17] The organic light-emitting device according to

[15] , 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.

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

[15] to

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

[19] The organic light-emitting device according to

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

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

[14] to

[19] , wherein the device is an organic electroluminescence device.

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

[14] to

[20] , which emits delayed fluorescence.

[0011] The compounds of the present invention are useful as light-emitting materials. The compounds of the present invention include compounds that exhibit excellent light-emitting properties. Furthermore, organic light-emitting devices using the compounds of the present invention include useful devices with high light-emitting efficiency and long device life.

[0012] The present invention will be described in detail below. The following description of the constituent elements may be based on typical embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, a numerical range expressed using "to" means a range including the numerical values ​​before and after "to" as the lower and upper limits. In addition, some or all of the hydrogen atoms present in the molecules of the compound used in the present invention may be replaced with deuterium atoms ( ２ In the chemical structural formulas herein, hydrogen atoms are represented by H or are omitted. For example, when the atom bonded to a carbon atom constituting the ring skeleton of a benzene ring is omitted, H is considered to be bonded to the carbon atom constituting the ring skeleton at the omitted location. In the chemical structural formulas herein, deuterium atoms are represented by D. Note that "luminous properties" in this application refer to properties related to luminescence, such as luminous efficiency, driving voltage, and luminous lifetime. The compound represented by general formula (1) has at least one excellent luminous property.

[0013] [Compound represented by general formula (1)]

[0014] In general formula (1), R １ and R ２ ~R ４wherein 0 to 1 independently represent a fused carbazol-9-yl group. The fused carbazol-9-yl group referred to here is a group having a structure in which a ring is fused to at least one of the two benzene rings constituting the carbazol-9-yl group, and is bonded via a nitrogen atom constituting the carbazole ring. The fused carbazol-9-yl group has 4 or more rings constituting the fused ring containing carbazole, more preferably 5 to 9, and even more preferably 5 to 7. In a preferred embodiment of the present invention, the number of rings constituting the fused ring containing carbazole is 5.

[0015] The ring fused to the carbazol-9-yl group is one ring or two or more fused rings selected from the group consisting of aromatic hydrocarbon rings, aromatic heterocycles, aliphatic hydrocarbon rings, and aliphatic heterocycles. When two or more rings are fused, they may be two or more fused rings of the same type, or two or more fused rings of different types. An example of the former is a naphthalene ring fused with two benzene rings, and an example of the latter is a benzofuran ring fused with a benzene ring and a furan ring. The fused ring is preferably one ring or two or more fused rings selected from the group consisting of aromatic hydrocarbon rings and aromatic heterocycles. An example of an aromatic hydrocarbon ring is a benzene 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 can 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. The nitrogen atom of the pyrrole ring is preferably bonded to a substituent selected from Substituent Group E, more preferably to an aryl group which may be substituted with an alkyl group or an aryl group. Preferred aromatic heterocycles are furan rings and thiophene rings. Examples of aliphatic hydrocarbon rings include cyclopentadiene rings.

[0016] In one embodiment of the present invention, the ring fused to the carbazol-9-yl group is selected from one ring or two or more fused rings selected from the group consisting of a benzene ring, a furan ring, a thiophene ring, a pyrrole ring, and a cyclopentadiene ring. In a preferred embodiment of the present invention, the ring is selected from one ring or two or more fused rings selected from the group consisting of a benzene ring, a furan ring, a thiophene ring, and a pyrrole ring. In a further preferred embodiment of the present invention, the ring is selected from one ring or two or more fused rings selected from the group consisting of a benzene ring, a furan ring, and a thiophene ring. In one embodiment of the present invention, the ring fused to the carbazol-9-yl group is a benzene ring, a naphthalene ring, a benzofuran ring, a benzothiophene ring, an indole ring, or an indene ring. In a preferred embodiment of the present invention, the ring fused to the carbazol-9-yl group is a benzene ring, a naphthalene ring, a benzofuran ring, or a benzothiophene ring. In a further preferred embodiment of the present invention, the ring fused to the carbazol-9-yl group is a benzene ring, a benzofuran ring, or a benzothiophene ring. In a particularly preferred embodiment of the present invention, the ring fused to the carbazol-9-yl group is a benzofuran ring or a benzothiophene ring. The benzofuran ring, benzothiophene ring, indole ring, and indene ring referred to here are five-membered rings fused to the benzene ring constituting the carbazol-9-yl group. The carbazol-9-yl group may be fused with one to four rings, preferably one or two rings, and more preferably one ring. When two or more rings are fused, the fused rings may be the same or different, but are preferably the same.

[0017] In the present invention, it is particularly preferable to employ a carbazol-9-yl group fused with a benzofuran ring or a carbazol-9-yl group fused with a benzothiophene ring as the fused carbazol-9-yl group. In the present invention, a benzofuro[2,3-a]carbazol-9-yl group can be employed as the carbazol-9-yl group fused with a benzofuran ring. A benzofuro[3,2-a]carbazol-9-yl group can also be employed. A benzofuro[2,3-b]carbazol-9-yl group can also be employed. A benzofuro[3,2-b]carbazol-9-yl group can also be employed. A benzofuro[2,3-c]carbazol-9-yl group can also be employed. A benzofuro[3,2-c]carbazol-9-yl group can also be employed. These structures are as follows, and at least one hydrogen atom in the following structures may be substituted. Furthermore, the benzene ring in the following structure may be further condensed with a ring, but a preferred embodiment is one in which no ring is condensed with the benzene ring in the following structure.

[0018] In the present invention, a benzothieno[2,3-a]carbazol-9-yl group can be used as the carbazol-9-yl group fused with a benzothiophene ring. A benzothieno[3,2-a]carbazol-9-yl group can also be used. A benzothieno[2,3-b]carbazol-9-yl group can also be used. A benzothieno[3,2-b]carbazol-9-yl group can also be used. A benzothieno[2,3-c]carbazol-9-yl group can also be used. A benzothieno[3,2-c]carbazol-9-yl group can also be used. These structures are as follows, and at least one hydrogen atom in the following structures may be substituted. Furthermore, the benzene ring in the following structures may be further fused with a ring, but an embodiment in which no ring is fused with the benzene ring in the following structures is preferred.

[0019] R in general formula (1) １is a fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are substituted on the carbon atoms constituting the ring skeleton. ２ ~R ４ When one of R is a fused carbazol-9-yl group, the fused carbazol-9-yl group may be a fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are substituted on the carbon atoms constituting the ring skeleton. １ and R ２ ~R ４The fused carbazol-9-yl groups in which two or more substituted or unsubstituted aryl groups are substituted on the ring skeleton carbon atoms, represented by one of the groups, may be the same or different. They are preferably the same. The number of substituted or unsubstituted aryl groups substituting the fused carbazol-9-yl group is preferably 2 to 10, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. In a preferred embodiment of the present invention, the number of substituted or unsubstituted aryl groups substituting the fused carbazol-9-yl group is 2. The substituted or unsubstituted aryl groups substituting the fused carbazol-9-yl group may be the same or different. In one embodiment of the present invention, all of the substituted or unsubstituted aryl groups substituting the fused carbazol-9-yl group are the same. The "aryl group" may be a monocyclic ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4. Specific examples of the ring include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a triphenylene ring. In one embodiment of the present invention, the aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthalen-1-yl group, or a substituted or unsubstituted naphthalen-2-yl group, preferably a substituted or unsubstituted phenyl group. The substituent of the aryl group may be selected, for example, from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In one embodiment of the present invention, the substituent of the aryl group is one group selected from the group consisting of an alkyl group, an aryl group, and a deuterium atom, or a group consisting of a combination of two or more groups. In a preferred embodiment of the present invention, the aryl group substituting the fused carbazol-9-yl group is unsubstituted.

[0020] Specific examples of substituted or unsubstituted aryl groups that can substitute for the fused carbazole-9-yl group are listed below. However, the substituted or unsubstituted aryl 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, * indicates the bonding position to the fused carbazole skeleton. In the following specific examples, methyl groups are omitted. For example, Ar4 is substituted with a methyl group, and Ar5 is substituted with an isopropyl group. * indicates the bonding position.

[0021]

[0022] Ar1 to Ar20 above, in which all hydrogen atoms have been replaced with deuterium atoms, are sequentially disclosed as Ar21 to Ar40. Ar4 to Ar20 above, in which all hydrogen atoms have been replaced with deuterium atoms in the phenyl or alkyl groups that are substituents, are sequentially disclosed as Ar41 to Ar57.

[0023] The substitution position of the substituted or unsubstituted aryl group on the fused carbazol-9-yl group is not particularly limited. In one embodiment of the present invention, 0 to 2 substituted or unsubstituted aryl groups are substituted on ring-structural carbon atoms of each ring constituting the fused carbazol-9-yl group, and preferably 0 to 1 substituted or unsubstituted aryl group is substituted on ring-structural carbon atoms of each ring constituting the fused carbazol-9-yl group. In a preferred embodiment of the present invention, at least one substituted or unsubstituted aryl group is substituted at the para-position of the benzene ring relative to the heteroatoms constituting the ring skeleton of the fused carbazol-9-yl group. In a preferred embodiment of the present invention, a substituted or unsubstituted aryl group is substituted only at the para-position of the benzene ring relative to the heteroatoms constituting the ring skeleton of the fused carbazol-9-yl group, and no substituted or unsubstituted aryl group is substituted on any other ring-structural carbon atoms. It should be noted that substituted or unsubstituted aryl groups bonded to heteroatoms (e.g., nitrogen atoms) constituting the ring skeleton of the fused carbazol-9-yl group are not counted in the number of substituted or unsubstituted aryl groups relative to the carbon atoms constituting the ring skeleton referred to herein. The carbon atoms constituting the ring skeleton of the fused carbazol-9-yl group may be substituted with two or more substituents other than substituted or unsubstituted aryl groups. For example, the carbon atoms may be further substituted with a substituent selected from Substituent Group A (excluding substituted or unsubstituted aryl groups), a substituent selected from Substituent Group B (excluding substituted or unsubstituted aryl groups), a substituent selected from Substituent Group C (excluding substituted or unsubstituted aryl groups), a substituent selected from Substituent Group D (excluding substituted or unsubstituted aryl groups), or a substituent selected from Substituent Group E (excluding substituted or unsubstituted aryl groups). In one embodiment of the present invention, the carbon atoms may be further substituted with a deuterium atom or an alkyl group optionally substituted with an aryl group, a deuterium atom, or both. In one embodiment of the present invention, the carbon atoms constituting the ring skeleton of the fused carbazol-9-yl group are not substituted with any substituent other than two or more substituted or unsubstituted aryl groups.The "alkyl group" referred to here may be linear, branched, or cyclic, with linear or branched being preferred. Two or more of the linear, cyclic, and branched groups may be mixed. The number of carbon atoms in the alkyl group may be, for example, 1 or more, 2 or more, or 4 or more. The number of carbon atoms may be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, an n-hexyl group, an isohexyl group, a 2-ethylhexyl group, an n-heptyl group, an isoheptyl group, an n-octyl group, an isooctyl group, an n-nonyl group, an isononyl group, an n-decanyl group, an isodecanyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.

[0024] A preferred fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are substituted on the carbon atoms constituting the ring skeleton is a group having a structure represented by the following general formula (2).

[0025] In the general formula (2), X is O, S, N(R ８ ) or C(R ９ ) (R １０ ) is preferably O, S or N(R ８ ), more preferably O or S. In a preferred embodiment of the present invention, X is O. In a preferred embodiment of the present invention, X is S. In general formula (2), (R ７ ) ｎ７ The benzene ring in the upper right corner to which (R ６ ) ｎ６The central benzene ring to which n is bonded is connected by a bond via X and a single bond, but the positional relationship of these two bonds is not limited. In the above general formula (2), the bond via X is written at the top and the single bond is written at the bottom. However, general formula (2) also includes a structure in which the bond via X is at the bottom and the single bond is at the top. In general formula (2), n5 and n7 each independently represent an integer of 0 to 4, preferably 0 to 2, and more preferably 0 or 1. n6 represents an integer of 0 to 2, and preferably 0 or 1. n5 + n6 + n7 is an integer of 2 to 10, preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 or 3. In a preferred embodiment of the present invention, n5 and n7 are 1, and n6 is 0. In another embodiment of the present invention, n5 and n6 are 1, and n7 is 0. In another embodiment of the present invention, n5, n6, and n7 are 1. In one embodiment of the present invention, n5 is 2, and n6 and n7 are 0. In another embodiment of the present invention, n7 is 2, and n5 and n6 are 0. In general formula (2), R ５ ~R ７ Each independently represents a substituent (the substituent also includes a deuterium atom). The substituent may be selected from, for example, Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. However, R present in the molecule ５ ~R ７ At least two of these are substituted or unsubstituted aryl groups. For the explanation and preferred range of the substituted or unsubstituted aryl group, please refer to the above description of "aryl group" and the description of the substituted or unsubstituted aryl group that can be substituted on the fused carbazol-9-yl group. In general formula (2), when R bonded to adjacent carbon atoms constituting the ring skeleton ５ R bonded to adjacent ring skeleton carbon atoms ６ R bonded to adjacent ring skeleton carbon atoms ７may be bonded to each other to form a cyclic structure. For the cyclic structure formed, the description of the ring fused to the carbazol-9-yl group above can be referred to. In one embodiment of the present invention, R bonded to adjacent carbon atoms constituting the ring skeleton ５ In one embodiment of the present invention, R bonded to adjacent carbon atoms forming the ring skeleton are bonded to each other to form a cyclic structure, preferably a benzofuro structure or a benzothieno structure. ７ are bonded to each other to form a ring structure, preferably a benzofuro structure or a benzothieno structure. ５ Comrade, R ６ Comrade, R ７ They are not bonded to each other to form a ring structure. ５ and R ６ , R ６ and R ７ do not bond to each other to form a cyclic structure. * in general formula (2) represents the bonding position with the benzene ring in general formula (1). In a preferred embodiment of the present invention, X is O, n5 and n7 are 1, n6 is 0 or 1, and R ５ and R ６ and R ７ or R ５ and R ７ is a substituted or unsubstituted aryl group. In a preferred embodiment of the present invention, X is S, n5 and n7 are 1, n6 is 0 or 1, and R ５ and R ６ and R ７ or R ５ and R ７ is a substituted or unsubstituted aryl group.

[0026] In the following, R in general formula (1) １ and R ２ ~R ４Specific examples of fused carbazol-9-yl groups in which two or more substituted or unsubstituted aryl groups are substituted on the carbon atoms constituting the ring skeleton, which can be employed as 0 to 1 of the above, are shown below. However, the fused carbazol-9-yl groups in which two or more substituted or unsubstituted aryl groups are substituted on the carbon atoms constituting the ring skeleton, which can be employed in the present invention, should not be construed as being limited by the following specific examples. In the following specific examples, * indicates the bonding position, and Ph represents a phenyl group. Methyl groups are not shown. For example, D181 to D240 have a methyl group.

[0027]

[0028] D297 to D592 are successively disclosed compounds in which all hydrogen atoms present in D1 to D296 have been replaced with deuterium atoms. D593 to D888 are successively disclosed compounds in which all hydrogen atoms present in the phenyl group (Ph) that is a substituent of D1 to D296 have been replaced with deuterium atoms. In one embodiment of the present invention, a fused carbazol-9-yl group having two or more substituted or unsubstituted aryl groups substituted on the carbon atoms constituting the ring skeleton is selected from D1 to D888. In one embodiment of the present invention, the group is selected from D1 to D240, D297 to D536, and D593 to D832. In another embodiment of the present invention, the group is selected from D241 to D296, D537 to D592, and D833 to D888. In one aspect of the present invention, the amine is selected from D1 to D120, D241 to D274, D297 to D416, D537 to D570, D593 to D712, and D833 to D866. In one aspect of the present invention, the amine is selected from D1 to D120, D297 to D416, and D593 to D712. In one aspect of the present invention, the amine is selected from D1 to D60, D241 to D257, D297 to D356, D537 to D553, D593 to D652, and D833 to D849. In one aspect of the present invention, the amine is selected from D61 to D120, D258 to D274, D357 to D416, D554 to D570, D653 to D712, and D850 to D866. In one aspect of the present invention, the compound is selected from D121 to D180, D275 to D285, D417 to D476, D571 to D581, D713 to D772, and D867 to D877. In one aspect of the present invention, the compound is selected from D181 to D240, D286 to D296, D477 to D536, D582 to D592, D773 to D832, and D878 to D888. In one aspect of the present invention, the compound is selected from D1 to D18. In one aspect of the present invention, the compound is selected from D19 to D36. In one aspect of the present invention, the compound is selected from D37 to D42. In one aspect of the present invention, the compound is selected from D43 to D60.

[0029] R in general formula (1) １ is a fused carbazol-9-yl having two or more substituted or unsubstituted aryl groups substituted on the ring skeleton carbon atoms, ２ ~R ４may be a fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are not substituted on the carbon atoms constituting the ring skeleton. ２ ~R ４ The 0 to 1 fused carbazol-9-yl may be further substituted with a substituent selected from Substituent Group A (except when substituted with two or more substituted or unsubstituted aryl groups), may be further substituted with a substituent selected from Substituent Group B (except when substituted with two or more substituted or unsubstituted aryl groups), may be further substituted with a substituent selected from Substituent Group C (except when substituted with two or more substituted or unsubstituted aryl groups), may be further substituted with a substituent selected from Substituent Group D (except when substituted with two or more substituted or unsubstituted aryl groups), or may be further substituted with a substituent selected from Substituent Group E (except when substituted with two or more substituted or unsubstituted aryl groups). In one embodiment of the present invention, the fused carbazol-9-yl group may be substituted with an alkyl group optionally substituted with a deuterium atom or an aryl group, a deuterium atom, or both. In another embodiment of the present invention, the fused carbazol-9-yl group may be further substituted with a deuterium atom. In another embodiment of the present invention, the fused carbazol-9-yl group is an unsubstituted fused carbazol-9-yl group.

[0030] In the following, R in general formula (1) ２ ~R ４ Specific examples of fused carbazol-9-yl groups in which two or more substituted or unsubstituted aryl groups are not substituted on the carbon atoms constituting the ring skeleton, and which can be employed as 0 to 1 of the above, are shown below. However, the fused carbazol-9-yl groups in which two or more substituted or unsubstituted aryl groups are not substituted on the carbon atoms constituting the ring skeleton and which can be employed in the present invention, should not be construed as being limited by the following specific examples. In the following specific examples, * indicates the bonding position, and Ph represents a phenyl group. Methyl groups are not shown. For this reason, D895 to D906 have a methyl group.

[0031]

[0032] D977 to D1064 are the groups in which all hydrogen atoms present in the above D889 to D976 have been replaced with deuterium atoms. D1065 to D1140 are the groups in which all hydrogen atoms present in the phenyl and methyl substituents of D895 to D911 and D918 to D976 have been replaced with deuterium atoms. In one embodiment of the present invention, a fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups do not substitute carbon atoms constituting the ring skeleton is selected from D889 to D1140. In one embodiment of the present invention, the group is selected from D889 to D953, D977 to D1041, and D1065 to D1117. In another embodiment of the present invention, the group is selected from D889 to D934, D977 to D1022, and D1065 to D1098. In one aspect of the present invention, the compound is selected from D889 to D911, D977 to D999, and D1065 to D1081. In one aspect of the present invention, the compound is selected from D912 to D934, D1000 to D1022, and D1082 to D1098. In one aspect of the present invention, the compound is selected from D935 to D953, D1023 to D1041, and D1099 to D1117. In one aspect of the present invention, the compound is selected from D954 to D976, D1042 to D1064, and D1118 to D1140.

[0033] R in general formula (1) ２ ~R ４ is a fused carbazol-9-yl group, and the other R ２ ~R ４ is a substituted or unsubstituted non-fused carbazol-9-yl group. ２ ~R ４ is a substituted or unsubstituted fused carbazol-9-yl group, and the other R ２ ~R ４ (i.e., R ２ ~R ４ In one embodiment of the present invention, R ２ is a substituted or unsubstituted fused carbazol-9-yl group, and R ３ and R４ are each independently a substituted or unsubstituted non-fused carbazol-9-yl group. ２ is a fused carbazol-9-yl group (R １ and R ２ may be different, but preferably R １ and R ２ are the same), and R ３ and R ４ are each independently a substituted or unsubstituted non-fused carbazol-9-yl group. ２ is a fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are not substituted on the ring skeleton carbon atoms, and R ３ and R ４ are each independently a substituted or unsubstituted non-fused carbazol-9-yl group. ３ is a substituted or unsubstituted fused carbazol-9-yl group, and R ２ and R ４ are each independently a substituted or unsubstituted non-fused carbazol-9-yl group. ３ is a fused carbazol-9-yl group (R １ and R ３ may be different, but preferably R １ and R ３ are the same), and R ２ and R ４ are each independently a substituted or unsubstituted non-fused carbazol-9-yl group. ３ is a fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are not substituted on the ring skeleton carbon atoms, and R ２ and R ４ are each independently a substituted or unsubstituted non-fused carbazol-9-yl group. ４ is a substituted or unsubstituted fused carbazol-9-yl group, and R ２ and R ３are each independently a substituted or unsubstituted non-fused carbazol-9-yl group. ４ is a fused carbazol-9-yl group (R １ and R ４ may be different, but preferably R １ and R ４ are the same), and R ２ and R ３ are each independently a substituted or unsubstituted non-fused carbazol-9-yl group. ４ is a fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are not substituted on the ring skeleton carbon atoms, and R ２ and R ３ are each independently a substituted or unsubstituted non-fused carbazol-9-yl group. ２ , R ３ , R ４ are each independently a substituted or unsubstituted non-fused carbazol-9-yl group.

[0034] R ２ ~R ４ The two to three substituted or unsubstituted non-fused carbazol-9-yl groups that R may have may be substituted with a substituent selected from Substituent Group A, may be substituted with a substituent selected from Substituent Group B, may be substituted with a substituent selected from Substituent Group C, may be substituted with a substituent selected from Substituent Group D, or may be substituted with a substituent selected from Substituent Group E. In one embodiment of the present invention, R ２ ~R ４ In one embodiment of the present invention, two or three non-fused carbazol-9-yl groups in R are substituted with a deuterium atom or an aryl group which may be substituted with an alkyl group. ２ ~R ４ In one embodiment of the present invention, two or three non-fused carbazol-9-yl groups in R are substituted with an alkyl group optionally substituted with a deuterium atom. ２ ~R ４In one embodiment of the present invention, two or three non-fused carbazol-9-yl groups in R are either substituted with a deuterium atom or unsubstituted. ２ ~R ４ The two or three non-fused carbazol-9-yl groups that may be present are all unsubstituted (i.e., an unsubstituted carbazol-9-yl group). When the non-fused carbazol-9-yl group is substituted, the substitution positions of the substituents are not particularly limited. In one embodiment of the present invention, each of the two benzene rings that constitute the non-fused carbazol-9-yl group is substituted with a substituent. In one embodiment of the present invention, only one of the two benzene rings that constitute the non-fused carbazol-9-yl group is substituted with a substituent. In one embodiment of the present invention, the non-fused carbazol-9-yl group has a substituent at the 3-position. In one embodiment of the present invention, the non-fused carbazol-9-yl group has a substituent at both the 3- and 6-positions. In one embodiment of the present invention, the non-fused carbazol-9-yl group has a substituent only at the 3-position. In one embodiment of the present invention, the non-fused carbazol-9-yl group has a substituent only at both the 3- and 6-positions.

[0035] R ２ ~R ４ The two or three substituted or unsubstituted non-fused carbazol-9-yl groups that R may have may be the same or different. ２ and R ３ In one aspect of the present invention, R ２ and R ４ In one aspect of the present invention, R ３ and R ４ In one aspect of the present invention, R ２ and R ３ and R ４ In one aspect of the present invention, R ２ and R ３ and R ４ are all different.

[0036] The substituted or unsubstituted non-fused carbazol-9-yl group is preferably a group having a structure represented by the following general formula (3):

[0037] In general formula (3), R １１and R １２ each independently represents a substituent (the substituent also includes a deuterium atom). For the substituent, the description of the substituent of the substituted or unsubstituted non-fused carbazol-9-yl group above can be referred to. In general formula (3), n11 and n12 each independently represent an integer of 0 to 4. In one embodiment of the present invention, R １１ and R １２ When R is a deuterium atom, n11 and n12 are 4. １１ and R １２ When R is a substituent other than a deuterium atom, n11 and n12 are preferably 0 to 2, for example, 0 or 1. In one embodiment of the present invention, both n11 and n12 are 0. In general formula (3), R １１ Comrade, R １２ R are not bonded to each other to form a single ring structure. １１ and R １２ In the general formula (3), one of the ring carbon atoms at positions 1 to 4 of the carbazole may be substituted with a nitrogen atom. Furthermore, one of the ring carbon atoms at positions 5 to 8 of the carbazole may be substituted with a nitrogen atom. In one embodiment of the present invention, one of the ring carbon atoms at positions 1 to 4 of the carbazole is substituted with a nitrogen atom, and the ring carbon atoms at positions 5 to 8 of the carbazole are not substituted with a nitrogen atom. For example, only the ring carbon atom at position 1 is substituted with a nitrogen atom. For example, only the ring carbon atom at position 2 is substituted with a nitrogen atom. For example, only the ring carbon atom at position 3 is substituted with a nitrogen atom. For example, only the ring carbon atom at position 4 is substituted with a nitrogen atom. For example, only the ring carbon atoms at positions 3 and 6 are substituted with nitrogen atoms. In one embodiment of the present invention, the ring carbon atoms at positions 1 to 8 of the carbazole are not substituted with a nitrogen atom. In the general formula (3), * indicates the bonding position to the benzene ring in the general formula (1). In a preferred embodiment of the present invention, R １１ and R １２are each independently a substituent selected from Substituent Group E, and n11 + n12 is 0 to 4, preferably 0 to 2. Examples include the case where n11 and n12 are both 1, the case where n11 is 1 and n12 is 0, and the case where n11 and n12 are both 0.

[0038] In the following, R ２ ~R ４ Specific examples of substituted or unsubstituted non-fused carbazol-9-yl groups that can be used are shown below. However, the substituted or unsubstituted non-fused carbazol-9-yl groups that can be used in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, * indicates a bonding position, and Ph represents a phenyl group. Methyl groups are not shown. For example, Z2 and Z3 have isopropyl groups, and Z4 and Z5 have methyl groups.

[0039]

[0040] Z27 to Z52 are successively disclosed as Z1 to Z26, in which all hydrogen atoms present in the Z1 to Z26 substituents have been replaced with deuterium atoms. Z53 to Z76 are successively disclosed as Z53 to Z76, in which all hydrogen atoms present in the phenyl and alkyl groups that are substituents of Z2 to Z21 and Z23 to Z26 have been replaced with deuterium atoms. In one embodiment of the present invention, a substituted or unsubstituted non-fused carbazol-9-yl group is selected from Z1 to Z76. In one embodiment of the present invention, the group is selected from Z1 to Z21, Z27 to Z47, and Z53 to Z72. In one embodiment of the present invention, the group is selected from Z1 to Z14, Z27 to Z40, and Z53 to Z65. In one embodiment of the present invention, the group is selected from Z15 to Z1, Z41 to Z47, and Z66 to Z72.

[0041] In a preferred embodiment of the present invention, R ２ ~R ４ are the same and are preferably non-fused carbazol-9-yl groups optionally substituted with a substituent selected from Substituent Group E, for example, non-fused carbazol-9-yl groups optionally substituted with a deuterium atom. In one embodiment of the present invention, R２ ~R ４ is a substituted or unsubstituted non-fused carbazol-9-yl group, and R ２ and R ３ In one aspect of the present invention, R ２ ~R ４ is a substituted or unsubstituted non-fused carbazol-9-yl group, and R ２ and R ４ In one aspect of the present invention, R ２ ~R ４ is a substituted or unsubstituted non-fused carbazol-9-yl group, and R ３ and R ４ In one aspect of the present invention, R ２ ~R ４ is a substituted or unsubstituted non-fused carbazol-9-yl group, and R ２ ~R ４ In one aspect of the present invention, R １ and R ２ is the same, and R ３ and R ４ In one aspect of the present invention, R １ and R ２ is the same, and R ３ and R ４ In one aspect of the invention, R １ and R ３ is the same, and R ２ and R ４ In one aspect of the present invention, R １ and R ３ is the same, and R ２ and R ４ In one aspect of the invention, R １ and R ４ is the same, and R ２ and R ３ In one aspect of the present invention, R １ and R ４ is the same, and R ２ and R ３ In one aspect of the invention, R ２ is a fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are not substituted on the ring skeleton carbon atoms, and R ３ and R４ In one aspect of the invention, R ２ is a fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are not substituted on the ring skeleton carbon atoms, and R ３ and R ４ In one aspect of the invention, R ３ is a fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are not substituted on the ring skeleton carbon atoms, and R ２ and R ４ In one aspect of the invention, R ３ is a fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are not substituted on the ring skeleton carbon atoms, and R ２ and R ４ In one aspect of the invention, R ４ is a fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are not substituted on the ring skeleton carbon atoms, and R ２ and R ３ In one aspect of the invention, R ４ is a fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are not substituted on the ring skeleton carbon atoms, and R ２ and R ３ In a preferred embodiment of the present invention, R １ The "substituted or unsubstituted aryl group" in the "fused carbazol-9-yl group having two or more substituted or unsubstituted aryl groups substituted on the ring-constituting carbon atoms" in the above is an aryl group in which at least one hydrogen atom present in the group is substituted with a deuterium atom, more preferably an aryl group in which all hydrogen atoms present in the group are substituted with deuterium atoms, and even more preferably a phenyl group in which all hydrogen atoms present in the group are substituted with deuterium atoms. In one preferred embodiment of the present invention, R １In the above, the "fused carbazol-9-yl group" in the "fused carbazol-9-yl group having two or more substituted or unsubstituted aryl groups substituted on the ring-constituting carbon atoms" is a carbazol-9-yl group fused with a benzofuran ring, and the "substituted or unsubstituted aryl group" substituted on the fused carbazol-9-yl group is an aryl group in which at least one hydrogen atom present in the group is substituted with a deuterium atom. In a more preferred embodiment of the present invention, R １ is a group represented by the following general formula (2a):

[0042]

[0043] In general formula (2a), R ５ａ ~R ７ａ each independently represents a hydrogen atom or an aryl group in which at least one hydrogen atom is substituted with a deuterium atom; R ５ａ ~R ７ａ At least two of R are aryl groups in which at least one of the hydrogen atoms is replaced with a deuterium atom. * indicates the bonding position. ５ａ and R ６ａ is an aryl group in which at least one hydrogen atom is replaced with a deuterium atom, and R ７ａ is preferably a hydrogen atom, and R ５ａ is a hydrogen atom, and R ６ａ and R ７ａ However, it is also preferable that the aryl group has at least one hydrogen atom substituted with a deuterium atom. The aryl group having at least one hydrogen atom substituted with a deuterium atom is preferably an aryl group having all hydrogen atoms present in the group substituted with deuterium atoms, and more preferably a phenyl group having all hydrogen atoms present in the group substituted with deuterium atoms.

[0044] In a preferred embodiment of the present invention, R １In the above formula, the "fused carbazol-9-yl group" in the "fused carbazol-9-yl group having two or more substituted or unsubstituted aryl groups substituted on the ring-constituting carbon atoms" is a carbazol-9-yl group to which a benzothiophene ring is fused, and the "substituted or unsubstituted aryl group" substituted on the fused carbazol-9-yl group is an aryl group in which at least one hydrogen atom present in the group is substituted with a deuterium atom. In a more preferred embodiment of the present invention, R １ is a group represented by the following general formula (2b):

[0045]

[0046] In general formula (2b), R ５ｂ ~R ７ｂ each independently represents a hydrogen atom or an aryl group in which at least one hydrogen atom is substituted with a deuterium atom; R ５ｂ ~R ７ｂ At least two of R are aryl groups in which at least one of the hydrogen atoms is replaced with a deuterium atom. * indicates the bonding position. ５ｂ and R ６ｂ is an aryl group in which at least one hydrogen atom is replaced with a deuterium atom, and R ７ｂ is preferably a hydrogen atom, and R ５ｂ is a hydrogen atom, and R ６ｂ and R ７ｂ However, it is also preferable that the aryl group has at least one hydrogen atom substituted with a deuterium atom. The aryl group having at least one hydrogen atom substituted with a deuterium atom is preferably an aryl group having all hydrogen atoms present in the group substituted with deuterium atoms, more preferably a phenyl group having all hydrogen atoms present in the group substituted with deuterium atoms. In one preferred embodiment of the present invention, R ２ ~R ４ is a non-fused carbazol-9-yl group in which at least one hydrogen atom present in the group is replaced with a deuterium atom, and more preferably is a non-fused carbazol-9-yl group in which all hydrogen atoms present in the group are replaced with deuterium atoms. In one preferred embodiment of the present invention, R ２ ~R ４are non-fused carbazol-9-yl groups in which at least one of the hydrogen atoms has been replaced with a deuterium atom, and have the same structure. １ The "substituted or unsubstituted aryl group" in the "fused carbazol-9-yl group having two or more substituted or unsubstituted aryl groups substituted on the ring-constituting carbon atoms" is an aryl group in which at least one hydrogen atom present in the group is substituted with a deuterium atom, and R ２ ~R ４ is a non-fused carbazol-9-yl group in which at least one hydrogen atom present in the group is replaced with a deuterium atom.

[0047] 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 atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, 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 atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Furthermore, the compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms. The compound represented by general formula (1) may be a compound composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen atoms. Furthermore, the compound represented by general formula (1) may be a compound containing deuterium atoms.

[0048] In the present specification, the term "substituent group A" refers to a deuterium atom, a hydroxyl group, a halogen atom (e.g., a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an alkylthio group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), an arylthio group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring skeleton atoms), a heteroaryloxy group (e.g., having 5 to 30 ring skeleton atoms), It means one atom or group, or a combination of two or more groups, selected from the group consisting of heteroarylthio groups (e.g., having 5 to 30 atoms constituting the ring skeleton), acyl groups (e.g., having 1 to 40 carbon atoms), alkenyl groups (e.g., having 1 to 40 carbon atoms), alkynyl groups (e.g., having 1 to 40 carbon atoms), alkoxycarbonyl groups (e.g., having 1 to 40 carbon atoms), aryloxycarbonyl groups (e.g., having 1 to 40 carbon atoms), heteroaryloxycarbonyl groups (e.g., having 1 to 40 carbon atoms), silyl groups (e.g., trialkylsilyl groups having 1 to 40 carbon atoms), and nitro groups. As used herein, "substituent group B" refers to one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 40 carbon atoms), an alkoxy group (e.g., having 1 to 40 carbon atoms), an aryl group (e.g., having 6 to 30 carbon atoms), an aryloxy group (e.g., having 6 to 30 carbon atoms), a heteroaryl group (e.g., having 5 to 30 ring atoms), a heteroaryloxy group (e.g., having 5 to 30 ring atoms), and a diarylamino group (e.g., having 0 to 20 carbon atoms). As used herein, "substituent group C" refers to one atom or group, or a combination of two or more selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), a heteroaryl group (e.g., having 5 to 20 ring atoms), and a diarylamino group (e.g., having 12 to 20 carbon atoms). As used herein, the term "substituent group D" refers to one atom or group, or a combination of two or more groups, selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), an aryl group (e.g., having 6 to 22 carbon atoms), and a heteroaryl group (e.g., having 5 to 20 ring skeleton atoms).As used herein, "substituent group E" refers to one atom or group, or a combination of two or more, selected from the group consisting of a deuterium atom, an alkyl group (e.g., having 1 to 20 carbon atoms), and an aryl group (e.g., having 6 to 22 carbon atoms). In the present specification, when "substituted or unsubstituted" or "optionally substituted" is described, the substituent may be selected, for example, from substituent group A, from substituent group B, from substituent group C, from substituent group D, or from substituent group E.

[0049] Specific examples of the compound represented by general formula (1) are shown in Tables 1 to 3 below. However, the compounds represented by general formula (1) that can be used in the present invention should not be construed as being limited by these specific examples. In Table 1, R １ ~R ４ The structures of compounds 1 to 888 are individually shown by specifying each compound. For example, in the case of compound 1, R １ is D1, R ２ ~R ４ In Table 2, each row shows the R of multiple compounds. １ ~R ４ The structures of compounds 1 to 67488 are shown by collectively displaying R ２ ~R ４ is fixed at Z1, and R １ In other words, the column of compounds 1 to 888 in Table 2 collectively displays compounds 1 to 888 specified in Table 1. Similarly, in the column of compounds 889 to 1776 in Table 2, R ２ ~R ４ is fixed at Z2, and R １ The compounds D1 to D888 are designated as compounds 889 to 1776. Compounds 1777 to 67488 in Table 2 are also identified in the same manner.

[0050] In Table 3, each row contains R １ ~R ４ The structures of Compounds 1 to 1975974 are shown by collectively displaying the formulas. Compounds 1 to 1463424 in Table 3 are R １ ~R ４ One or two of the above are any of D1 to D888, and R ２ ~R ４ In each row of Table 2, Z1 to Z76 are fixed to one, and D1 to D888 are sequentially changed to identify the compound. Then, Z1 to Z76 are fixed to the next one, and D1 to D888 are sequentially changed to identify the compound. That is, the row of Compounds 1 to 67488 in Table 3 collectively displays Compounds 1 to 67488 identified in Table 2. In the row of Compounds 67489 to 134088 in Table 3, R ２ and R ３ is Z2 and R ４ is fixed at Z1, and R １ The compounds having R1 to R888 are compounds 67489 to 68376, respectively. ２ and R ３ is Z3, R ４ is fixed at Z1, and R １ The compounds having R1 to R888 are compounds 68377 to 69264, respectively. ２ and R ３ is Z4, R ４ is fixed at Z1, and R １ The compounds 69265 to 70152 are compounds in the order of D1 to D888, and R ２ and R ３ is Z76, R ４ is fixed at Z1, and R １ Compounds 11425 to 11592 are identified in the same manner as above. Compounds 134089 to 1463424 in Table 3 are identified in the same manner as above. １ is D1 and R ２~R ４ One of them is Z1, and R ２ ~R ４ The other one of D2 to D1140 is any one of D2 to D1140, and R ２ ~R ４ The remaining one is one of Z2 to Z76. Here, first, Z2 to Z76 are fixed to one, and D2 to D1140 are sequentially changed to identify the compound. Then, Z2 to Z76 are fixed to the next one, and D2 to D1140 are sequentially changed to identify the compound. In the case of the row of compounds 1463425 to 1548849, R １ is D1, and R ３ is Z1, and R ４ is fixed at Z2, and R ２ The compounds having D2 to D1140 are compounds 1463425 to 1464563, respectively, and R １ is D1, and R ３ is Z1, and R ４ is fixed at Z3, and R ２ The compounds having D2 to D1140 are compounds 1464564 to 1465702, respectively, and R １ is D1, and R ３ is Z1, and R ４ is fixed at Z4, and R ２ The compounds in which R is D2 to D1140 are compounds 1465703 to 1466841, respectively. １ is D1, and R ３ is Z1, and R ４ is fixed to Z35, R ２ The compounds having the formula D2 to D246 are compounds 1547711 to 1548849. Compounds 1548850 to 1975974 are also identified in the same manner.

[0051]

[0052] All compounds identified by the above numbers are considered to be individually disclosed. In addition, when rotamers exist among the specific examples of the compounds, the mixture of rotamers and each separated rotamer are also considered to be disclosed in the present specification.

[0053] In one embodiment of the present invention, a compound is selected from compounds 1 to 1975974. In one embodiment of the present invention, a compound is selected from compounds 1 to 861360. In one embodiment of the present invention, a compound is selected from compounds 861361 to 1975974. In one embodiment of the present invention, a compound is selected from compounds 1 to 67488. In one embodiment of the present invention, a compound is selected from compounds 67489 to 467088. In one embodiment of the present invention, a compound is selected from compounds 467089 to 861360. In one embodiment of the present invention, a compound is selected from compounds 861361 to 1063824. In one embodiment of the present invention, a compound is selected from compounds 1608325 to 1463424. In one embodiment of the present invention, a compound is selected from compounds 1463425 to 1975974. In one embodiment of the present invention, a compound is selected from compounds 67489 to 467088 and 1063825 to 1463424. In one embodiment of the present invention, the compound is selected from compounds 467089 to 861360, and 1463425 to 1975974. In one embodiment of the present invention, the compound is selected from compounds 861361 to 928848, 1063825 to 1130424, 1263625 to 1330224, 1463425 to 1548849, and 1719700 to 1805124. In one embodiment of the present invention, the compound is selected from compounds 928849 to 996336, 1130425 to 1197024, 1330225 to 1396824, 1548850 to 1634274, and 1805125 to 1890549. In one aspect of the present invention, the compound is selected from compounds 996337-1063824, 1197025-1263624, 1396825-1463424, 1634275-1719699, and 1890550-1975974.

[0054] In the above, specific examples of compounds in which all of the substituted or unsubstituted aryl groups contained in D1 to D888 are unsubstituted phenyl groups (Ar1) or phenyl groups substituted with deuterium atoms (Ar21) are identified as compounds 1 to 1975974. Table 4 shows the substituted or unsubstituted aryl groups (Ar21) present in D1 to D175308 contained in each of compounds 1 to 1975974. １ , Ar ２The compounds in which the unsubstituted phenyl group (Ar1) or deuterium-substituted phenyl group (Ar21) in the compound 1975974 is changed as shown in Table 4 are listed in order in the table format. In Table 4, compounds 1 to 1975974 are also listed to make the correspondence easier to understand. For example, compound 1 (1) indicates a compound having a structure in which each unsubstituted phenyl group (Ar1) present in D1 of compound 1 is substituted with a 2-naphthyl group (Ar2). Furthermore, compound 2 (1) indicates a compound having a structure in which each unsubstituted phenyl group (Ar1) present in D2 of compound 2 is substituted with a 2-naphthyl group (Ar2). Compound 1975974 (1) indicates a compound having a structure in which each unsubstituted phenyl group (Ar1) present in D1 of compound 1975974 is substituted with a 2-naphthyl group (Ar2). Compounds 1(2) to 1975974(2) and subsequent compounds are identified in the same manner. １ and Ar ２ is the same.

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

[0056] The molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, when, for example, an organic layer containing the compound represented by general formula (1) is intended to be formed into a film by a vapor deposition method and used. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by general formula (1). The compound represented by general formula (1) may be formed into a film by a coating method regardless of its molecular weight. By using a coating method, it is possible to form a film even from a compound with a relatively large molecular weight. The compound represented by general formula (1) has the advantage of being easily soluble in organic solvents. Therefore, the compound represented by general formula (1) is easy to apply a coating method to and is also easy to purify to increase its purity.

[0057] By applying the present invention, it is also conceivable to use a compound containing multiple structures represented by general formula (1) in its molecule as a light-emitting material. For example, it is conceivable to use a polymer obtained by pre-preparing a polymerizable group in the structure represented by general formula (1) and polymerizing the polymerizable group as a light-emitting material. For example, it is conceivable to prepare a monomer containing a polymerizable functional group at any site of general formula (1) and polymerize it alone or copolymerize it with other monomers to obtain a polymer having repeating units, and use the polymer as a light-emitting material. Alternatively, it is conceivable to couple compounds having a structure represented by general formula (1) together to obtain a dimer or trimer, and use these as a light-emitting material.

[0058] Examples of polymers having a repeating unit containing a structure represented by general formula (1) include polymers containing a structure represented by either of the following two general formulas.

[0059] In the above general formula, Q represents a group containing a structure represented by general formula (1), L １ and L ２ represents a linking group. The number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10. The linking group is -X １１ -L １１ Preferably, X has a structure represented by the formula: １１ represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. １１ represents a linking group, and is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group. １０１ , R １０２ , R １０３ and R １０４each independently represents a substituent. Preferably, it is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom, and even more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, or an unsubstituted alkoxy group having 1 to 3 carbon atoms. L １ and L ２ The linking group represented by the following formula (1) can be bonded to any site of Q. Two or more linking groups may be bonded to one Q to form a crosslinked structure or a network structure.

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

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

[0062] A polymer containing a structure represented by general formula (1) in its molecule may be a polymer consisting only of repeating units having the structure represented by general formula (1), or may be a polymer containing repeating units having other structures. Furthermore, the repeating units having the structure represented by general formula (1) contained in the polymer may be of a single type, or may contain two or more types. Examples of repeating units that do not have the structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. Examples include repeating units derived from monomers having an ethylenically unsaturated bond, such as ethylene and styrene.

[0063] In some embodiments, the compound represented by general formula (1) is a light-emitting material. In some embodiments, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence. In some embodiments of the present disclosure, the compound represented by general formula (1), when excited by thermal or electronic means, can emit light in the UV region, the blue, green, yellow, orange, or red region of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm), or the near-infrared region. In some embodiments of the present disclosure, the compound represented by general formula (1), when excited by thermal or electronic means, can emit light in the orange or yellow region of the visible spectrum (about 570 nm to about 620 nm, e.g., 570 to 590 nm). In some embodiments of the present disclosure, an organic semiconductor device can be fabricated using the compound represented by general formula (1). The organic semiconductor device referred to here may be an organic optical device mediated by light or an organic device not mediated by light. The organic optical element may be an organic light-emitting element that emits light, an organic light-receiving element that receives light, or an element that causes energy transfer by light within the element. In some embodiments of the present disclosure, an organic optical element such as an organic electroluminescence element or a solid-state imaging element (e.g., a CMOS image sensor) can be fabricated using a compound represented by general formula (1). In some embodiments of the present disclosure, a CMOS (complementary metal oxide semiconductor) or the like can be fabricated using a compound represented by general formula (1).

[0064] The electronic properties of small molecule chemical libraries can be calculated using well-known ab initio quantum chemical calculations. For example, time-dependent density functional theory using a basis set known as 6-31G* and the Becke three-parameter Lee-Yang-Parr hybrid functional can be used to analyze the Hartree-Fock equations (TD-DFT / B3LYP / 6-31G*) and screen for molecular fragments (moieties) with HOMOs above a certain threshold and LUMOs below a certain threshold. Thus, donor moieties ("D") can be selected if they have a HOMO energy (e.g., ionization potential) above -6.5 eV, for example. Acceptor moieties ("A") can be selected if they have a LUMO energy (e.g., electron affinity) below -0.5 eV, for example. The bridging moiety ("B") prevents overlap between the π-conjugated systems of the donor and acceptor moieties, for example, by providing a strongly conjugated system that can tightly constrain the acceptor and donor moieties into specific configurations. In certain embodiments, compound libraries are screened using one or more of the following properties: 1. Emission near a specific wavelength; 2. Calculated triplet state above a specific energy level; 3. ΔE below a specific value. ＳＴ 4. Quantum yield above a certain value 5. HOMO level 6. LUMO level In some embodiments, the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K (ΔE ＳＴ ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In some embodiments, ΔE ＳＴ The quantum yield of the compound represented by formula (1) is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV. In certain embodiments, the compound represented by formula (1) exhibits a quantum yield of greater than 25%, e.g., about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.

[0065] [Method for synthesizing a compound represented by general formula (1)] The compound represented by general formula (1) includes a novel compound. The compound represented by general formula (1) can be synthesized by combining known reactions. For example, R １ is a halogen atom, and then reacting the resulting compound with a fused carbazole having two or more substituted or unsubstituted aryl groups substituted on the carbon atoms constituting the ring skeleton, thereby synthesizing the compound of general formula (1). For details of the reaction conditions, please refer to the synthesis examples described below.

[0066] Compositions Using Compounds of Formula (1) In some embodiments, compounds of Formula (1) may be combined with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) that disperse, covalently bond, coat, support, or associate with the compounds to form a solid film or layer. For example, compounds of Formula (1) may be combined with electroactive materials to form a film. In some cases, compounds of Formula (1) may be combined with hole transporting polymers. In some cases, compounds of Formula (1) may be combined with electron transporting polymers. In some cases, compounds of Formula (1) may be combined with hole transporting and electron transporting polymers. In some cases, compounds of Formula (1) may be combined with copolymers having both hole transporting and electron transporting moieties. In these embodiments, electrons and / or holes formed in the solid film or layer may interact with the compounds of Formula (1).

[0067] [Film Formation] In some embodiments, a film containing a compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution containing a composition containing the compound of the present invention is applied to a surface, and a film is formed after removing the solvent. Examples of wet processes include, but are not limited to, spin coating, slit coating, inkjet (spray) printing, gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In some embodiments, a substituent (e.g., an alkyl group) that increases the solubility in organic solvents can be introduced into the compound contained in the composition. In some embodiments, a film containing the compound of the present invention can be formed by a dry process. In some embodiments, a vacuum deposition method can be used as the dry process, but is not limited to this. When using a vacuum deposition method, the compounds constituting the film may be co-deposited from separate deposition sources, or may be co-deposited from a single deposition source containing a mixture of compounds. When a single deposition source is used, a mixed powder of compound powders may be used, a compression molded product obtained by compressing the mixed powder may be used, or a mixture of the individual compounds may 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 having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source. A film having a desired composition ratio can be easily formed by mixing multiple compounds in the same composition ratio as the composition ratio of the film to be formed and using the resulting deposition source. In some embodiments, a temperature at which the weight loss rates of the co-deposited compounds are the same can be identified, and this temperature can be used as the temperature during co-deposition.

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

[0069] Emitting Layer: In some embodiments, the emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons. In some embodiments, the layer emits light. In some embodiments, only an emitting material is used as the emitting layer. In some embodiments, the emitting layer includes an emitting material and a host material. In some embodiments, the emitting material is one or more compounds represented by general formula (1). In some embodiments, to improve the light emission efficiency of organic electroluminescent devices and organic photoluminescent devices, singlet and triplet excitons generated in the emitting material are confined within the emitting material. In some embodiments, a host material is used in addition to the emitting material in the emitting layer. In some embodiments, the host material is an organic compound. In some embodiments, the organic compound has excited singlet and triplet energies, at least one of which is higher than those of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons generated in the emitting material of the present invention are confined within the molecules of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons are sufficiently confined to improve the light emission efficiency. In some embodiments, singlet and triplet excitons are not sufficiently confined while still achieving high light emission efficiency; that is, any host material capable of achieving high light emission efficiency can be used in the present invention without particular limitations. In some embodiments, light emission occurs in the light-emitting material in the light-emitting layer of the device of the present invention. In some embodiments, the emitted light includes both fluorescence and delayed fluorescence. In some embodiments, the emitted light includes light emitted from the host material. In some embodiments, the emitted light consists of light emitted from the host material. In some embodiments, the emitted light includes light emitted from the compound represented by general formula (1) and light emitted from the host material. In some embodiments, a TADF molecule and a host material are used. In some embodiments, TADF is an assist dopant, and has a lower excited singlet energy than the host material in the light-emitting layer and a higher excited singlet energy than the light-emitting material in the light-emitting layer.

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

[0071] Examples of light-emitting materials that can be used in combination with the assist dopant having the structure represented by general formula (1) include compounds represented by the following general formula (4).

[0072]

[0073] In the general formula (4), X １ and X ２ Each independently represents O or S. １ and Y ２ are each independently a single bond, O, S or C(R ａ ) (R ｂ ) represents. １ ~R ２２ , R ａ , R ｂ each independently represents a hydrogen atom, a deuterium atom, or a substituent, and R １ ~R ２２ At least one of R is a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ５ and R ６ , R ６ and R ７ , R７ and Y １ , Y １ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １６ and R １７ , R １７ and R １８ , R １８ and Y ２ , Y ２ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ may be bonded to each other to form a cyclic structure. In a preferred embodiment, they are not bonded to each other to form a cyclic structure. ２１ and R １ , R ４ and R ５ , R １０ and R １２ , R １５ and R １６ are not bonded to each other to form a cyclic structure. １ , C-R ２ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ , C-R １７ , C-R １８ , C-R １９ , C-R ２０ , C-R２１ , C-R ２２ may be substituted with N, but is preferably not substituted with N.

[0074] R １ ~R ２２ is preferably a group consisting of one or a combination of two or more selected from the group consisting of a hydrogen atom, a deuterium atom, an alkyl group, and an aryl group (some or all of the hydrogen atoms in the group may be substituted with deuterium atoms), or a substituted or unsubstituted diarylamino group (two aryl groups constituting the diarylamino group may be linked to each other via a linking group). １ ~R ２２ Preferably, at least one of R is an aryl group optionally substituted with one or more groups selected from the group consisting of a deuterium atom, an alkyl group, and an aryl group. １ ~R ２２ Among them, R ２ , R ３ , R ６ , R ９ , R １３ , R １４ , R １７ , R ２０ Preferably, only 1 to 6 selected from the group consisting of R １ ~R ２２ The total number of carbon atoms in R is preferably 10 to 60, １ ~R ２２ In a preferred embodiment, the total number of benzene rings in Y is 2 to 6. １ and Y ２ is a single bond. In a preferred embodiment, X １ and X ２ is O. In a preferred embodiment, it has a point-symmetric structure.

[0075] The compound represented by general formula (4) preferably has, for example, any of the following skeletal structures. In a preferred embodiment, it has any of the skeletal structures in Group 1 below. In a preferred embodiment, it has any of the skeletal structures in Group 2 below. In a preferred embodiment, it has any of the skeletal structures in Group 3 below. In a preferred embodiment, it has any of the skeletal structures in Group 4 below. In a preferred embodiment, it has any of the skeletal structures in Group 5 below. In the skeletal structures below, X represents O or S, and Y represents O, S, or C(R ａ ) (R ｂ ) (preferably O or S), R ａ and R ｂ is as defined in general formula (4). At least one hydrogen atom in the following skeleton may be substituted with a substituent containing a deuterium atom. The substituent may be selected from, for example, substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E.

[0076]

[0077] Specific examples of the compound represented by formula (4) are listed below, but the compounds of formula (4) that can be used in the present invention are not to be construed as being limited to these specific examples.

[0078] Examples of light-emitting materials that can be used in combination with the assist dopant having the structure represented by general formula (1) include pyrromethene boron complex compounds, such as those represented by the following general formula (5):

[0079] In general formula (5), R ３１ ~R ３７ each independently represents a hydrogen atom or a substituent (the substituent also includes a deuterium atom), R ３１ and R ３２ , R ３２ and R ３３ , R ３３ and R３４ , R ３４ and R ３５ , R ３５ and R ３６ , R ３６ and R ３７ may be bonded to each other to form a cyclic structure. ３８ and R ３９ each independently represents one atom or group selected from the group consisting of a halogen atom, an alkyl group, an aryl group, an alkoxy group, and an aryloxy group, or a group consisting of a combination of two or more of these. Specific examples of the compound represented by general formula (5) include the compounds described in paragraphs 0196 to 0255 of WO 2012 / 015177.

[0080] Further, examples of light-emitting materials that can be used in combination with an assist dopant having a structure represented by general formula (1) include the compounds described in paragraph 0050 of JP-A No. 2022-027733 and the compounds described in paragraphs 0220 to 0239 of WO 2015 / 022974.

[0081] Further preferred light-emitting materials include compounds represented by the following general formula (E1).

[0082] In general formula (E1), R １ , R ３ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. ２ represents an acceptor group, or R １ and R ２ are bonded to each other to form an acceptor group, or R ２ and R ３ are bonded to each other to form an acceptor group. ３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ９ and R １０ , R １０ and R１１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ may be bonded to each other to form a cyclic structure. １ represents O or NR, and R represents a substituent. ２ ~X ４ Of these, X ３ and X ４ At least one of C-R is O or NR, and the remaining may be O or NR or may not be linked. When they are not linked, each end independently represents a hydrogen atom, a deuterium atom, or a substituent. １ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0083] Further preferred light-emitting materials include compounds represented by the following general formula (E2).

[0084] In general formula (E2), R １ and R ２ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; R ３ ~R １６ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ３ , R ３ and R ４ , R ４ and R５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R ２ , R ２ and R １０ , R １０ and R １１ , R １１ and R １２ , R １２ and R １３ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １ may be bonded to each other to form a cyclic structure. ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ , C-R １０ , C-R １１ , C-R １２ , C-R １３ , C-R １４ , C-R １５ , C-R １６ may be substituted with N.

[0085] Further preferred light-emitting materials include compounds represented by the following general formula (E3).

[0086] In formula (E3), Z １ and Z ２ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ ~R ９ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R３ and R ４ , R ４ and R ５ , R ５ and R ６ , R ７ and R ８ , R ８ and R ９ may be bonded to each other to form a cyclic structure. １ , Z ２ , R １ and R ２ are bonded to each other to form a ring, R ２ and R ３ are bonded to each other to form a ring, R ４ and R ５ are bonded to each other to form a ring, and R ５ and R ６ at least one of the rings formed by bonding together is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole, and R １ ~R ９ At least one of Z is a substituted or unsubstituted aryl group or an acceptor group, or １ and Z ２ At least one of the C-R rings has an aryl group or an acceptor group as a substituent. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. １ , C-R ２ , C-R ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ may be substituted with N.

[0087] Further preferred light-emitting materials include compounds represented by the following general formula (E4).

[0088] In formula (E4), Z １represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z ２ and Z ３ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R １ represents a hydrogen atom, a deuterium atom or a substituent, R ２ and R ３ each independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. １ and R １ , R ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ may be bonded to each other to form a cyclic structure. ２ and Z ２ , Z ２ and Z ３ , Z ３ and R ３ At least one pair of these is bonded to each other to form a ring structure.

[0089] Further preferred light-emitting materials include compounds represented by the following general formula (E5).

[0090] In general formula (E5), R １ and R ２ each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group; Z １ and Z ２ each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R ３ ~R ９ each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ , R ２ , Z １ and Z ２At least one of R contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring. １ and Z １ , Z １ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and Z ２ , Z ２ and R ２ , R ２ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １ may be bonded to each other to form a cyclic structure. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. ３ , C-R ４ , C-R ５ , C-R ６ , C-R ７ , C-R ８ , C-R ９ may be substituted with N.

[0091] Further preferred light-emitting materials include compounds represented by the following general formula (E6).

[0092] In general formula (E6), X １ and X ２ is a nitrogen atom on one side and a boron atom on the other side. １ ~R ２６ , A １ , A ２ R each independently represents a hydrogen atom, a deuterium atom, or a substituent. １ and R ２ , R ２ and R ３ , R ３ and R ４ , R４ and R ５ , R ５ and R ６ , R ６ and R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R １０ , R １０ and R １１ , R １１ and R １２ , R １３ and R １４ , R １４ and R １５ , R １５ and R １６ , R １６ and R １７ , R １７ and R １８ , R １８ and R １９ , R １９ and R ２０ , R ２０ and R ２１ , R ２１ and R ２２ , R ２２ and R ２３ , R ２３ and R ２４ , R ２４ and R ２５ , R ２５ and R ２６ may be bonded to each other to form a cyclic structure. １ is a nitrogen atom, R １７ and R １８ are bonded to each other as a single bond to form a pyrrole ring, and X ２ is a nitrogen atom, R ２１ and R ２２ are bonded to each other to form a single bond to form a pyrrole ring. １ is a nitrogen atom, and R ７ and R ８ and R ２１ and R ２２ are bonded via a nitrogen atom to form a 6-membered ring, and R １７ and R １８ are bonded to each other to form a single bond, R １ ~R ６At least one of R is a substituted or unsubstituted aryl group, or １ and R ２ , R ２ and R ３ , R ３ and R ４ , R ４ and R ５ , R ５ and R ６ are bonded to each other to form an aromatic ring or a heteroaromatic ring.

[0093] Further preferred light-emitting materials include compounds represented by the following general formula (E7).

[0094] In general formula (E7), R ２０１ ~R ２２１ R each independently represents a hydrogen atom, a deuterium atom, or a substituent, and preferably represents a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, or a group in which an alkyl group and an aryl group are bonded. ２０１ and R ２０２ , R ２０２ and R ２０３ , R ２０３ and R ２０４ , R ２０５ and R ２０６ , R ２０６ and R ２０７ , R ２０７ and R ２０８ , R ２１４ and R ２１５ , R ２１５ and R ２１６ , R ２１６ and R ２１７ , R ２１８ and R ２１９ , R ２１９ and R ２２０ , R ２２０ and R ２２１ At least one pair of R is bonded to each other to form a benzofuro structure or a benzothieno structure. ２０１ and R ２０２ , R ２０２ and R ２０３ , R ２０３ and R ２０４ , R ２０５ and R ２０６ , R ２０６ and R ２０７, R ２０７ and R ２０８ and one or two pairs of R ２１４ and R ２１５ , R ２１５ and R ２１６ , R ２１６ and R ２１７ , R ２１８ and R ２１９ , R ２１９ and R ２２０ , R ２２０ and R ２２１ One or two of the groups bond together to form a benzofuro structure or a benzothieno structure. ２０３ and R ２０４ are bonded to each other to form a benzofuro or benzothieno structure, and even more preferably R ２０３ and R ２０４ , R ２１６ and R ２１７ are bonded to each other to form a benzofuro structure or a benzothieno structure. Particularly preferably, R ２０３ and R ２０４ , R ２１６ and R ２１７ are bonded to each other to form a benzofuro structure or a benzothieno structure, and R ２０６ and R ２１９ is a substituted or unsubstituted aryl group (preferably a substituted or unsubstituted phenyl group, more preferably an unsubstituted phenyl group). Furthermore, compounds represented by the general formula (1) described in the specifications of Japanese Patent Application Nos. 2021-103698, 2021-103699, 2021-103700, 2021-081332, 2021-103701, 2021-151805, and 2021-188860 can be used as light-emitting materials. These descriptions of general formula (1) and specific compounds are herein cited as part of this specification.

[0095] In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 0.1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 50% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 20% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 10% by weight or less. In some embodiments, the host material in the light-emitting layer is an organic compound having hole-transporting and electron-transporting functions. In some embodiments, the host material in the light-emitting layer is an organic compound that prevents the wavelength of emitted light from increasing. In some embodiments, the host material in the light-emitting layer is an organic compound having a high glass transition temperature.

[0096] In some embodiments, the host material is selected from the group consisting of:

[0097] In some embodiments, the light-emitting layer contains two or more types of TADF molecules with different structures. For example, the light-emitting layer may contain three materials, the host material, the first TADF molecule, and the second TADF molecule, whose excited singlet energy levels are higher in this order. In this case, the first TADF molecule and the second TADF molecule both have a difference ΔE between their lowest excited singlet energy levels and the lowest excited triplet energy level at 77 K. ＳＴis preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, even more preferably 0.1 eV or less, even more preferably 0.07 eV or less, even more preferably 0.05 eV or less, even more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less. The concentration of the first TADF molecules in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. Also, the concentration of the host material in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. The concentration of the first TADF molecules in the light-emitting layer may be greater than, less than, or the same as the concentration of the host material. In some embodiments, the composition in the light-emitting layer may be 10 to 70 wt % of the host material, 10 to 80 wt % of the first TADF molecules, and 0.1 to 30 wt % of the second TADF molecules. In one embodiment, the composition within the light-emitting layer may be 20 to 45 wt % of the host material, 50 to 75 wt % of the first TADF molecules, and 5 to 20 wt % of the second TADF molecules. In one embodiment, the luminescence quantum yield φPL1(A) upon photoexcitation of a co-deposited film of the first TADF molecules and the host material (wherein the concentration of the first TADF molecules in this co-deposited film is A wt %) and the luminescence quantum yield φPL2(A) upon photoexcitation of a co-deposited film of the second TADF molecules and the host material (wherein the concentration of the second TADF molecules in this co-deposited film is A wt %) satisfy the relationship φPL1(A) > φPL2(A). In some embodiments, the luminescence quantum yield φPL2(B) upon photoexcitation of a co-deposited film of the second TADF molecule and the host material (where the concentration of the second TADF molecule in this co-deposited film is B wt %) and the luminescence quantum yield φPL2(100) upon photoexcitation of a film of the second TADF molecule alone satisfy the relationship φPL2(B) > φPL2(100). In some embodiments, the emitting layer may contain three types of TADF molecules with different structures. The compound of the present invention may be any of the multiple TADF compounds contained in the emitting layer. In some embodiments, the emitting layer may be composed of a material selected from the group consisting of a host material, an assist dopant, and an emitting material. In some embodiments, the emitting layer does not contain a metal element.In some embodiments, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can be made of a material consisting of only atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. When the light-emitting layer contains a TADF material other than the compound of the present invention, the TADF material can be a known delayed fluorescent material. Preferred delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 011955, and paragraph 0008 of WO2013 / 081088. to 0071 and 0118 to 0133, paragraphs 0009 to 0046 and 0093 to 0134 of JP 2013-256490 A, paragraphs 0008 to 0020 and 0038 to 0040 of JP 2013-116975 A, paragraphs 0007 to 0032 and 0079 to 0084 of WO 2013 / 133359 A, paragraph 0 of WO 2013 / 161437 A JP-A-2014-9352, paragraphs 0007 to 0041 and 0060 to 0069, JP-A-2014-9224, paragraphs 0008 to 0048 and 0067 to 0076, JP-A-2017-119663, paragraphs 0013 to 0025, JP-A-2017-119664, paragraphs 0013 to 0026, JP-A-2017-119665, Compounds encompassed by the general formulas described in paragraphs 0012 to 0025 of JP-A No. 017-222623, paragraphs 0010 to 0050 of JP-A No. 2017-226838, paragraphs 0012 to 0043 of JP-A No. 2018-100411, and paragraphs 0016 to 0044 of WO2018 / 047853, particularly exemplified compounds, which are capable of emitting delayed fluorescence, are included.Further, here, the following patent documents are disclosed: JP 2013-253121 A, WO 2013 / 133359 A, WO 2014 / 034535 A, WO 2014 / 115743 A, WO 2014 / 122895 A, WO 2014 / 126200 A, WO 2014 / 136758 A, WO 2014 / 133121 A, WO 20 14 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008 580 publication, WO2014 / 203840 publication, WO2015 / 002213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP2015-129240A, WO2015 / 129714, WO2015 / 129715, WO2015 / 13350 Preferably, the luminescent materials capable of emitting delayed fluorescence are those described in WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541. The above publications described in this paragraph are incorporated herein by reference.

[0098] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0099] Substrate: In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate, which is not particularly limited and may be any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon.

[0100] Anode: In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or higher). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is CuI, indium tin oxide (ITO), SnO ２ and ZnO. In some embodiments, IDIXO (In ２ O ３ An amorphous material capable of forming a transparent conductive film, such as ZnO, is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is formed by evaporation or sputtering. In some embodiments, the film is patterned by a photolithography method. In some embodiments, if the pattern does not need to be highly accurate (e.g., greater than about 100 μm), the pattern may be formed using a mask with a shape suitable for evaporation or sputtering of the electrode material. In some embodiments, when a coating material such as an organic conductive compound can be applied, a wet film formation method such as a printing method or a coating method is used. In some embodiments, when emitted light passes through the anode, the anode has a transmittance of more than 10%, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0101] Cathode: In some embodiments, the cathode is made of an electrode material such as a metal with a low work function (4 eV or less) (referred to as an electron-injecting metal), an alloy, a conductive compound, or a combination thereof. In some embodiments, the electrode material is sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al ２ O３ In some embodiments, a mixture of an electron-injecting metal and a second metal is used, the second metal being a stable metal having a higher work function than the electron-injecting metal. In some embodiments, the mixture is selected from a magnesium-silver mixture, a magnesium-aluminum mixture, a magnesium-indium mixture, an aluminum-aluminum oxide (Al ２ O ３ ) mixture, a lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron injection properties and oxidation resistance. In some embodiments, the cathode is fabricated by forming an electrode material as a thin film by evaporation or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the cathode has a thickness of 10 nm to 5 μm. In some embodiments, the cathode has a thickness of 50 to 200 nm. In some embodiments, either the anode or the cathode of the organic electroluminescent device is transparent or semitransparent to transmit emitted light. In some embodiments, a transparent or semitransparent electroluminescent device improves light radiance. In some embodiments, the cathode is formed from a conductive, transparent material as described above for the anode, thereby forming a transparent or semitransparent cathode. In some embodiments, the device includes an anode and a cathode, both of which are transparent or semitransparent.

[0102] Injection Layer: The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the emissive layer or the hole transport layer, and between the cathode and the emissive layer or the electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present. Below are examples of preferred compounds that can be used as hole injection materials:

[0103]

[0104] Next, preferred examples of compounds that can be used as the electron injection material will be listed.

[0105] Barrier layer: A barrier layer is a layer that can prevent charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outside the light-emitting layer. In some embodiments, an electron blocking layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole blocking layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a barrier layer prevents excitons from diffusing outside the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer constitute an exciton blocking layer. As used herein, the terms "electron blocking layer" or "exciton blocking layer" include layers that have both the functions of an electron blocking layer and an exciton blocking layer.

[0106] Hole Blocking Layer: The hole blocking layer functions as an electron transporting layer. In some embodiments, during electron transport, the hole blocking layer prevents holes from reaching the electron transporting layer. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the hole blocking layer may be the same materials as those described above for the electron transporting layer. Examples of preferred compounds that can be used for the hole blocking layer are listed below.

[0107]

[0108] Electron Blocking Layer: The electron blocking layer transports holes. In some embodiments, during hole transport, the electron blocking layer prevents electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the electron blocking layer may be the same materials as those described above for the hole transport layer. Specific examples of preferred compounds that can be used as electron blocking materials are listed below.

[0109]

[0110] Exciton Blocking Layer: The exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the emissive layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer allows for effective confinement of excitons in the emissive layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton blocking layer is adjacent to the emissive layer on either the anode side or the cathode side, and on both sides. In some embodiments, when the exciton blocking layer is present on the anode side, it may be present between the hole transport layer and the emissive layer and adjacent to the emissive layer. In some embodiments, when the exciton blocking layer is present on the cathode side, it may be present between the emissive layer and the cathode and adjacent to the emissive layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is present between the anode and the exciton blocking layer adjacent to the emissive layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or a similar layer is present between the cathode and the exciton blocking layer adjacent to the emissive layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and excited triplet energy, respectively, of the light-emitting material.

[0111] Hole Transport Layer: The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material has one of the following properties: hole injection or transport and electron blocking. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from a porphyrin compound, an aromatic tertiary amine compound, and a styrylamine compound. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are listed below.

[0112]

[0113] 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.

[0114]

[0115] 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.

[0116]

[0117] 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.

[0118] Devices: In some embodiments, the light-emitting layer is incorporated into a device. For example, devices include, but are not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, mobile phones, and tablets. In some embodiments, the electronic device comprises an OLED having an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the compositions can be useful for facilitating charge or energy transfer within the device and / or as hole transport materials. Such devices include, for example, organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quenched devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0119] Bulb or Lamp: In some embodiments, an electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the device comprises OLEDs of different colors. In some embodiments, the device comprises an array comprising a combination of OLEDs. In some embodiments, the combination of OLEDs is a three-color combination (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a two-color, four-color, or more-color combination. In some embodiments, the device is an OLED light comprising: a circuit board having a first side with a mounting surface and an opposite second side, the circuit board defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration including an anode, a cathode, and at least one organic layer including an emissive layer between the anode and the cathode; a housing for the circuit board; and at least one connector disposed on an end of the housing, the housing and the connector defining a package suitable for attachment to a lighting fixture. In some embodiments, the OLED light has multiple OLEDs mounted on the circuit board such that light is emitted in multiple directions. In some embodiments, a portion of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

[0120] Displays or Screens: In some embodiments, the light-emitting layers of the present invention can be used in screens or displays. In some embodiments, the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the substrate is a photoplate structure useful for two-sided etching to provide pixels with unique aspect ratios. The screen (also called a mask) is used in the manufacturing process of OLED displays. The corresponding artwork pattern design allows for the placement of very steep, narrow tie bars between pixels in the vertical direction and large, wide, beveled openings in the horizontal direction. This allows for the fine patterning of pixels required for high-resolution displays while optimizing chemical vapor deposition on the TFT backplane. Internal pixel patterning allows for the construction of three-dimensional pixel openings with various aspect ratios in the horizontal and vertical directions. Furthermore, the use of imaged "stripes" or halftone circles in pixel regions protects etching in certain areas until these specific patterns are undercut and removed from the substrate. At that time, all pixel areas experience similar etching rates, but their depth varies depending on the halftone pattern. Varying the size and spacing of the halftone patterns allows for etching with varying degrees of protection within a pixel, enabling the deep, localized etching required to create steep vertical bevel angles. A preferred material for the deposition mask is Invar. Invar is a metal alloy cold-rolled into long, thin sheets at steel mills. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable, low-cost method for creating open areas in a deposition mask is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography).In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In further embodiments, the screen or display pattern is fabricated using plasma etching.

[0121] Device Manufacturing Method: OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarization film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel. OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarization film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel.

[0122] Another aspect of the present invention provides a method for manufacturing an organic light-emitting diode (OLED) display, the method including: forming a barrier layer on a base substrate of a mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer on each of the display units of the cell panel; and applying an organic film to an interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example, made of SiNx, and edges of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film assists in soft cutting of the mother panel into cell panel units. In some embodiments, the thin film transistor (TFT) layer includes a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may include a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is made of the same material as the planarization film and is formed simultaneously with the formation of the planarization film. In some embodiments, the light-emitting units are coupled to the TFT layer by a passivation layer, a planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting units. In some embodiments of the manufacturing method, the organic film is not coupled to either the display unit or the encapsulation layer.

[0123] Each of the organic film and the planarization film may comprise one of polyimide and acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may further include attaching a carrier substrate formed of a glass material to one surface of the base substrate formed of polyimide before forming a barrier layer on the other surface of the base substrate, and separating the carrier substrate from the base substrate before cutting along the interface. In some embodiments, the OLED display is a flexible display. In some embodiments, the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film, like the organic film formed on the edge of the barrier layer, is formed of polyimide or acrylic. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer, such that a portion of the organic film is in direct contact with the base substrate and a remaining portion of the organic film is in contact with the barrier layer while surrounding the edge of the barrier layer.

[0124] In some embodiments, the light-emitting layer includes a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode. In some embodiments, the pixel electrode is connected to a source / drain electrode of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, causing the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image-forming unit including a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, an encapsulation layer that covers the display unit and prevents penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films are alternately stacked. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which multiple thin films are stacked. In some embodiments, the organic film applied to the interface portion is disposed at a distance from each of the multiple display units. In some embodiments, the organic film is formed such that a portion of the organic film directly contacts the base substrate, and a remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

[0125] In one embodiment, the OLED display is flexible and uses a flexible base substrate made of polyimide. In some embodiments, the base substrate is formed on a carrier substrate made of a glass material, and then the carrier substrate is separated. In some embodiments, a barrier layer is formed on the surface of the base substrate opposite the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, while the base substrate is formed on all surfaces of the mother panel, the barrier layer is formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0126] In some embodiments, the manufacturing method further includes a step of cutting along the interface, in which a groove is formed in the barrier layer and at least a portion of the organic film is formed in the groove, so that the groove does not penetrate into the base substrate. In some embodiments, a TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are disposed on and cover the TFT layer. At the same time as the planarization film, made of, for example, polyimide or acrylic, is formed, the grooves at the interface are covered with an organic film, made of, for example, polyimide or acrylic. This prevents cracks from occurring when each cell panel is cut along the grooves at the interface by allowing the organic film to absorb any impact that occurs. That is, if all barrier layers were completely exposed without the organic film, the impact would be transmitted to the barrier layer when each cell panel is cut along the grooves at the interface, thereby increasing the risk of cracks. However, in one embodiment, the grooves at the interface between the barrier layers are covered with an organic film to absorb any impact that would otherwise be transmitted to the barrier layer, allowing each cell panel to be cut softly and preventing cracks from occurring in the barrier layer. In one embodiment, the organic film and the planarization film covering the groove of the interface portion are spaced apart from each other. For example, if the organic film and the planarization film are connected to each other as one layer, external moisture may penetrate into the display unit through the planarization film and the remaining portion of the organic film, so the organic film and the planarization film are spaced apart from each other such that the organic film is spaced apart from the display unit.

[0127] In some embodiments, the display units are formed by forming light-emitting units, and an encapsulation layer is disposed on the display units to cover the display units. Thus, after the mother panel is completely manufactured, the carrier substrate supporting the base substrate is separated from the base substrate. In some embodiments, a laser beam is irradiated onto the carrier substrate, causing the carrier substrate to separate from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into individual cell panels. In some embodiments, the mother panel is cut along the interfaces between the cell panels using a cutter. In some embodiments, the grooves at the interfaces along which the mother panel is cut are covered with an organic film, which absorbs impact during cutting. In some embodiments, cracks in the barrier layer can be prevented during cutting. In some embodiments, the method reduces the product defect rate and stabilizes its quality. Another aspect is an OLED display having a barrier layer formed on a base substrate, display units formed on the barrier layer, an encapsulation layer formed on the display units, and an organic film applied to edges of the barrier layer.

[0128] The features of the present invention will be explained in more detail below with reference to synthesis examples and examples. The materials, processing details, processing procedures, etc. shown below can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. The emission characteristics were evaluated using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334). The HOMO and LUMO energies were measured by atmospheric photoelectron spectroscopy (Riken Keiki AC-3, etc.). In the synthesis examples below, compounds represented by general formula (1) were synthesized.

[0129] (Synthesis Example 1) Synthesis of Compound 1 Compound a

[0130] Under a nitrogen stream, an N,N-dimethylformamide solution (120 mL) of 2-bromo-3,5,6-trifluorotetranitrile (1.1 g, 4.14 mmol), 9H-carbazole (2.1 g, 12.6 mmol), and potassium carbonate (2.9 g, 20.7 mmol) was stirred at room temperature for 16 hours. Water and methanol were then added to precipitate a solid, which was then collected by filtration. The collected reaction mixture was purified by silica gel column chromatography (toluene / hexane = 4 / 1) and reprecipitation (toluene / hexane) to obtain compound a (1.3 g, 1.9 mmol, yield 45%). 1 H NMR (400 MHz, CDCl3) δ 8.24-8.20 (m, 2H), 7.72-7.57 (m, 6H), 7.47-7.44 (m, 2H), 7.33-7.29 (m, 2H), 7.13-6.93 (m, 12H). ASAP mass spectrometry: calculated 701.12, observed 702.02

[0131] Compound 1

[0132] Under a nitrogen stream, an N,N-dimethylformamide solution (30 mL) of compound a (1.0 g, 1.4 mmol), 2,8-diphenyl-5H-benzofuro[3,2-c]carbazole (0.8 g, 1.9 mmol), and potassium carbonate (0.3 g, 2.2 mmol) was heated and stirred at 120°C for 16 hours. The mixture was then returned to room temperature, and water and methanol were added to precipitate a solid, which was then collected by filtration. The collected reaction mixture was purified by silica gel column chromatography (toluene / hexane = 5 / 1) and reprecipitation (toluene / methanol) to obtain compound 1 (1.0 g, 1.0 mmol, yield 68%). 1H NMR (400 MHz, CDCl3) δ 8.39 (s, 1H), 8.15 (s, 1H), 7.82 (d, J = 8.8 Hz, 1H), 7.77-7.67 (m, 13H), 7.54-7.49 (m, 4H), 7.44-7.28 (m, 10H), 7.22-7.14 (m, 10H), 7.10-7.07 (m, 2H). ASAP mass spectrum analysis: theoretical value 1030.34, observed value 1031.11

[0133] (Synthesis Example 2) Synthesis of Compound 23722 Compound b

[0134] Under a nitrogen atmosphere, 12H-[1]benzofuro[2,3-a]carbazole (4.10 g, 15.9 mmol), N-bromosuccinimide (5.67 g, 31.9 mmol), and chloroform (80 mL) were placed in a 200 mL three-neck flask and stirred at room temperature for 2 hours. After stirring, water was added to the reaction solution, which was then filtered and extracted. The resulting reaction mixture was purified by silica gel column chromatography to obtain compound b (4.00 g, 9.64 mmol, yield 60%). 1 H NMR (400 MHz, CDCl3) δ 8.61 (dq, J = 7.8, 0.7 Hz, 2H), 8.20-8.18 (m, 1H), 8.11 (d, J = 0.7 Hz, 1H), 7.65 (dt, J = 8.4, 0.7 Hz, 1H), 7.57-7.51 (m, 2H), 7.47-7.41 (m, 2H) ASAP mass spectrum analysis: theoretical value 412.91, observed value 414.91.

[0135] compound c

[0136] Under a nitrogen atmosphere, compound b (4.00 g, 9.64 mmol), phenyl-d5-boronic acid (2.94 g, 23.1 mmol), tetrakis(triphenylphosphine)palladium(0) (0.835 g, 0.723 mmol), tripotassium phosphate (6.14 g, 28.9 mmol), and a mixed solvent of 1,4-dioxane (90 mL) / water (30 mL) were placed in a 300 mL three-neck flask and stirred at 100°C for 15 hours. After stirring, the reaction solution was cooled to room temperature, water was added, and the mixture was filtered and extracted. The resulting reaction mixture was purified by silica gel column chromatography to obtain compound c (2.56 g, 6.10 mmol, yield 63%). 1 H NMR (400 MHz, CDCl3) δ 8.58 (s, 1H), 8.34 (t, J = 0.9 Hz, 1H), 7.99 (d, J = 0.5 Hz, 1H), 7.74 (dd, J = 8.5, 1.8 Hz, 1H), 7.67-7.62 (m, 2H), 7.57-7.52 (m, 1H), 7.44-7.40 (m, 1H), 7.19-7.15 (m, 1H) ASAP mass spectrum analysis: theoretical value 419.21, observed value 420.37.

[0137] Compound 23722

[0138] Under a nitrogen atmosphere, 2-bromo-3,5,6-tris(9H-carbazol-9-yl-d8)terephthalonitrile (0.922 g, 1.27 mmol), compound c (0.798 g, 1.90 mmol), cesium carbonate (0.579 g, 1.78 mmol), and dimethylformamide (20 mL) were placed in a 100 mL three-neck flask and stirred at 110°C for 2 hours, after which the mixture was cooled to room temperature. Water was added to the reaction solution, and the precipitated solid was collected by filtration and washed with methanol. The resulting solid was purified by silica gel column chromatography to obtain compound 23722 (0.82 g, 0.77 mmol, yield 61%). 1H NMR (400 MHz, CDCl3) δ 8.01 (d, J = 8.0 Hz, 1H), 7.90 (s, 1H), 7.73-7.68 (m, 2H), 7.63 (d, J = 7.8 Hz, 1H), 7.36 (t, J = 7.4 Hz, 1H), 7.03 (dd, J = 13.6, 8.6 Hz, 2H) ASAP mass spectrum analysis: theoretical value 1064.56, observed value 1066.16.

[0139] (Synthesis Example 3) Synthesis of Compound 23764 Compound d

[0140] Under a nitrogen atmosphere, acetic acid (880 ml) and concentrated sulfuric acid (0.1 ml) were added sequentially to a mixture of 4-bromodibenzothiophene (38.0 g, 144 mmol), (diacetoxyiodo)benzene (32.6 g, 101 mmol), and iodine (25.7 g, 101 mmol), and the mixture was allowed to react overnight. Saturated aqueous sodium bisulfite solution (50 ml) was added to the reaction solution to terminate the reaction, followed by the addition of purified water. The precipitated solid was collected by filtration and washed with purified water. The resulting solid was extracted with dichloromethane and aqueous sodium bicarbonate solution and dried over anhydrous magnesium sulfate. The solution was filtered through a Celite / silica gel pad, and the solvent was evaporated to give compound d (40.5 g, 104 mmol, yield 72.1%). 1 H NMR (400 MHz, CDCl) δ 8.44 (d, J = 1.7 Hz, 1H), 8.05 (dd, J = 8.0, 0.9 Hz, 1H), 7.76 (dd, J = 8.0, 1.7 Hz, 1H), 7.66-7.61 (m, 2H), 7.36 (t, J = 8.0 Hz, 1H). ASAP mass spectrometry: calcd 389.05, observed 389.96.

[0141] compound e

[0142] Under a nitrogen atmosphere, a degassed mixed solvent of toluene (70 mL), ethanol (10 mL), and water (20 mL) was added to a mixture of compound d (14.5 g, 37.2 mmol), phenyl-d5-boronic acid (4.73 g, 37.2 mmol), dichlorobis(triphenylphosphine)palladium (1.31 g, 1.86 mmol), and potassium carbonate (10.3 g, 74.4 mmol), and the mixture was reacted at 70°C for 7 hours. After completion of the reaction, the reaction solution was cooled to room temperature and extracted. The resulting reaction mixture was purified by silica gel column chromatography to obtain compound e (9.9 g, 28.8 mmol, yield 93.9%). 1 H NMR (400 MHz, CDCl) δ 8.30 (d, J = 1.8 Hz, 1H), 8.18 (dd, J = 7.9, 1.0 Hz, 1H), 7.95 (dd, J = 8.2, 0.7 Hz, 1H), 7.74 (dd, J = 8.2, 1.8 Hz, 1H), 7.64 (dd, J = 7.8, 0.9 Hz, 1H), 7.36 (t, J = 7.8 Hz, 1H). ASAP mass spectrometry: calculated 344.28, observed 345.11.

[0143] compound f

[0144] Under a nitrogen atmosphere, degassed toluene (100 mL) and 2-chloroaniline (3.30 mL, 31.6 mmol) were added sequentially to a mixture of compound e (9.90 g, 28.8 mmol), palladium acetate (0.646 g, 2.88 mmol), bis[2-(diphenylphosphino)phenyl]ether (2.32 g, 4.31 mmol), and sodium tert-butoxide (5.53 g, 57.5 mmol), and the mixture was allowed to react at 125°C for 12 hours. After completion of the reaction, the reaction solution was cooled to room temperature and filtered through a Celite / silica gel pad. The resulting reaction mixture was purified by silica gel column chromatography to yield compound f (8.10 g, 20.7 mmol, 72.1% yield). 1H NMR (400 MHz, CDCl3) δ 8.36 (d, J = 1.8 Hz, 1H), 8.01 (dd, J = 7.8, 0.9 Hz, 1H), 7.92 (dd, J = 8.7, 0.9 Hz, 1H), 7.72 (dd, J = 8.2, 1.8 Hz, 1H), 7.48 (t, J = 7.8 Hz, 1H), 7.44-7.39 (m, 2H), 7.16-7.04 (m, 2H), 6.88-6.82 (m, 1H), 6.19 (s, 1H). ASAP mass spectrum analysis: theoretical value 390.94, observed value 391.19.

[0145] compound g

[0146] Under a nitrogen atmosphere, dimethylacetamide (80 mL) was added to a mixture of compound f (8.10 g, 20.7 mmol), palladium acetate (0.466 g, 2.07 mmol), tricyclohexylphosphonium tetrafluoroborate (1.53 g, 4.15 mmol), and cesium carbonate (20.3 g, 62.2 mmol), and the mixture was reacted at 140 °C for 13 hours. After completion of the reaction, the reaction solution was cooled to room temperature and filtered through a Celite / silica gel pad. The resulting reaction mixture was purified by silica gel column chromatography to obtain compound g (8.10 g, 20.7 mmol, 72.1% yield). 1 H NMR (400 MHz, CDCl) δ 8.45 (d, J = 1.8 Hz, 1H), 8.32 (s, 1H), 8.22-8.09 (m, 3H), 7.99 (dd, J = 8.2, 0.5 Hz, 1H), 7.72 (dd, J = 9.4, 1.8 Hz, 1H), 7.57 (dt, J = 8.2, 0.7 Hz, 1H), 7.47 (td, J = 7.9, 1.1 Hz, 1H), 7.31 (td, J = 7.9, 1.1 Hz, 1H). ASAP mass spectrometry: calculated 354.48, observed 355.23.

[0147] compound h

[0148] Under a nitrogen atmosphere, compound g (2.00 g, 5.64 mmol) was added to chloroform (100 ml) and cooled to 0°C. N-bromosuccinimide (1.00 g, 5.64 mmol) was then added and the mixture was allowed to react at room temperature for 3 hours. The resulting reaction solution was extracted and purified by silica gel column chromatography to give compound h (1.06 g, 2.45 mmol, yield 43.4%). ASAP mass spectrometry analysis: theoretical 432.03, observed 432.33.

[0149] compound i

[0150] Under a nitrogen atmosphere, a degassed mixture of toluene (24 mL), ethanol (16 mL), and water (8 mL) was added to a mixture of compound h (1.00 g, 2.31 mmol), phenyl-d5-boronic acid (0.438 g, 3.44 mmol), dichlorobis(triphenylphosphine)palladium (0.081 g, 0.12 mmol), and potassium carbonate (0.800 g, 5.79 mmol), and the mixture was reacted at 90°C for 2 hours. After completion of the reaction, the reaction solution was cooled to room temperature and extracted. The resulting reaction mixture was purified by silica gel column chromatography to give compound i (0.960 g, 2.20 mmol, 95.2% yield). ASAP mass spectrometry analysis: calculated 435.61, observed 436.45. 1 H NMR (400 MHz, CDCl3) δ 8.33 (s, 1H), 8.11 (d, J = 8.0, 1H), 8.00 (s, 1H), 7.95 (d, J = 8.5, 1H), 7.68-7.38 (m, 5H).

[0151] Compound 23764

[0152] Under a nitrogen atmosphere, dimethylformamide (100 mL) was added to a mixture of compound i (0.506 g, 1.16 mmol), 2-bromo-3,5,6-tris(9H-carbazol-9-yl-d8)terephthalonitrile (0.650 g, 0.89 mmol), and cesium carbonate (0.35 g, 1.07 mmol), and the mixture was stirred at 110°C for 3 hours. After completion of the reaction, the reaction solution was cooled to room temperature, and water was added to quench the reaction. The precipitated solid was collected by filtration and washed with methanol. The obtained solid was purified by silica gel column chromatography to obtain compound 23764 (0.600 g, 0.555 mmol, yield 62.0%). 1 H NMR (400 MHz, CDCl) δ 8.06 (dd, J = 8.24, 0.7 Hz, 1H), 7.77 (dd, J = 8.24, 1.8 Hz, 1H), 7.71 (s, 1H), 7.39-7.22 (m, 2H), 7.10-6.93 (m, 3H). ASAP mass spectrometry: calculated 1081.46, observed 1082.13.

[0153] (Synthesis Example 4) Synthesis of Compound 23782 Compound j

[0154] Under a nitrogen atmosphere, 12H-[1]benzothieno[2,3-a]carbazole (5.17 g, 18.9 mmol), N-bromosuccinimide (6.73 g, 37.8 mmol), and chloroform (200 mL) were placed in a 300 mL three-neck flask and stirred at room temperature for 2 hours. After stirring, water was added to the reaction solution, followed by filtration and extraction. The extracted reaction mixture was purified by silica gel column chromatography to obtain compound j (5.20 g, 12.1 mmol, yield 64%). 1 H NMR (400 MHz, CDCl3) δ 9.35-9.32 (m, 1H), 8.31-8.25 (m, 2H), 8.20 (d, J = 1.8 Hz, 1H), 7.95-7.93 (m, 1H), 7.59-7.52 (m, 3H), 7.41 (d, J = 8.6 Hz, 1H). ASAP mass spectrometry: calcd 428.88, obs. 430.99.

[0155] compound k

[0156] Under a nitrogen atmosphere, compound j (5.15 g, 11.9 mmol), phenyl-d5-boronic acid (3.64 g, 28.7 mmol), tetrakis(triphenylphosphine)palladium(0) (1.04 g, 0.896 mmol), tripotassium phosphate (7.61 g, 35.8 mmol), and a mixed solvent of 1,4-dioxane (120 mL) / water (40 mL) were placed in a 300 mL three-neck flask and stirred at 100°C for 15 hours. After stirring, the mixture was cooled to room temperature, and water was added to the reaction solution, followed by filtration and extraction. The resulting reaction mixture was purified by silica gel column chromatography to obtain compound k (2.32 g, 5.33 mmol, yield 45%). 1 H NMR (400 MHz, CDCl3) δ 8.35 (s, 1H), 8.31 (d, J = 1.6 Hz, 1H), 8.00 (d, J = 0.7 Hz, 1H), 7.92-7.90 (m, 1H), 7.73 (dd, J = 8.4, 1.7 Hz, 1H), 7.63 (dd, J = 8.5, 0.7 Hz, 1H), 7.38-7.34 (m, 1H), 7.21-7.18 (m, 1H), 7.15-7.10 (m, 1H). ASAP mass spectrometry: calculated 435.19, observed 436.37.

[0157] Compound 23782

[0158] Under a nitrogen atmosphere, 2-bromo-3,5,6-tris(9H-carbazol-9-yl-d8)terephthalonitrile (0.650 g, 0.894 mmol), compound k (0.584 g, 1.34 mmol), cesium carbonate (0.408 g, 1.25 mmol), and dimethylformamide (20 mL) were placed in a 100 mL three-neck flask and stirred at 110°C for 2 hours, then cooled to room temperature. Water was added to this reaction solution, and the precipitated solid was collected by filtration and washed with methanol. The resulting solid was purified by silica gel column chromatography to obtain compound 23782 (0.50 g, 0.46 mmol, yield 52%). 1H NMR (400 MHz, CDCl3) δ 8.01 (d, J = 7.8 Hz, 1H), 7.84 (d, J = 1.5 Hz, 1H), 7.68 (s, 1H), 7.50-7.46 (m, 1H), 7.22-7.13 (m, 3H), 7.05 (d, J = 8.5 Hz, 1H). ASAP mass spectrometry: calculated 1080.53, observed 1082.08.

[0159] (Comparative Synthesis Example 1) Synthesis of Comparative Compound C1

[0160] Under a nitrogen stream, an N,N-dimethylformamide solution (20 mL) of compound a (0.6 g, 0.9 mmol), 2-phenyl-5H-benzofuro[3,2-c]carbazole (0.4 g, 1.1 mmol), and potassium carbonate (0.2 g, 1.3 mmol) was heated and stirred at 120°C for 7 hours. The mixture was then returned to room temperature, and water and methanol were added to precipitate a solid, which was then collected by filtration. The collected reaction mixture was purified by silica gel column chromatography (toluene / hexane = 5 / 1) and reprecipitation (toluene / methanol) to obtain compound C1 (0.6 g, 0.6 mmol, yield 75%). 1 H NMR (400 MHz, CDCl3) δ 8.38 (s, 1H), 7.97 (d, J = 8.0 Hz 1H), 7.82-7.67 (m, 10H), 7.53-7.38 (m, 10H), 7.34-7.28 (m, 4H), 7.24-7.13 (m, 10H), 7.07-7.05 (m, 2H). ASAP mass spectrum analysis: theoretical value 954.31, observed value 955.68

[0161] (Example 1) Preparation and evaluation of thin film A thin film was prepared by vacuum deposition on a quartz substrate at a vacuum level of 1×10 －３ Compound 1 and mCBP were evaporated from different evaporation sources under conditions of less than 10 Pa to form a 100 nm thick doped thin film containing 20 wt % Compound 1. A doped thin film was formed in the same manner using comparative compound C1 instead of Compound 1. The maximum emission wavelength (λmax) was measured when each doped thin film was irradiated with 300 nm excitation light.

[0162] Example 2: Preparation and evaluation of organic electroluminescence device using compound 1. Each thin film was formed on a glass substrate on which an anode made of indium tin oxide (ITO) with a thickness of 50 nm was formed by vacuum deposition at a vacuum degree of 5.0×10 －５ The layers were laminated at 100 Pa. First, HAT-CN was formed on ITO to a thickness of 10 nm, NPD was formed thereon to a thickness of 35 nm, and PTCz was further formed thereon to a thickness of 10 nm. Next, H1, Compound 1, and the light-emitting material EM1 were co-deposited from different evaporation sources at concentrations of 69.5 wt%, 30.0 wt%, and 0.5 wt%, respectively, to form a 40 nm thick layer, which served as the light-emitting layer. Next, ET1 was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-deposited 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, resulting in an organic electroluminescence device. Each organic electroluminescence device was fabricated in the same manner as above, except that comparative compound C1 was used in place of compound 1. The external quantum efficiency (EQE) of each organic electroluminescence device at 6.3 mA and 12.6 mA / cm ２ The time (LT95) elapsed until the luminescence intensity reached 95% of that at the start of the test was measured, and the results are shown in Table 5. LT95 is expressed as a relative value when the LT95 of the element using comparative compound C1 is set to 1.

[0163]

[0164] (Example 3) Preparation and Evaluation of Thin Films Compound 23722, 23764, or 23782 was used instead of Compound 1 to form each doped thin film in the same manner as in Example 1. Each doped thin film thus formed was irradiated with 300 nm excitation light, and the maximum emission wavelength (λmax) was measured. The results are shown in Table 6.

[0165] (Example 4) Preparation and evaluation of organic electroluminescence device using compound 23722, 23764, or 23782 Each organic electroluminescence device was prepared by the same procedure as in Example 2, except that compound 23722, 23764, or 23782 was used instead of compound 1. The external quantum efficiency (EQE) of each organic electroluminescence device at 6.3 mA was measured, and the results are shown in Table 6.

[0166]

[0167] The results of measurements in Examples 1 to 4 confirmed that the use of the compound represented by general formula (1) can improve the luminous efficiency of the device, extend the device life, and improve durability. It was also found that the use of a compound in which the hydrogen atoms of the aryl group and the non-fused carbazol-9-yl group are substituted with deuterium atoms can further improve the luminous efficiency of the device.

[0168] By using the compound represented by general formula (1), an organic light-emitting device having good light-emitting properties can be provided. Therefore, the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1): 【Chemistry 1】 [In general formula (1), R １ and R ２ ~R ４ 0 to 1 of R each independently represent a substituted or unsubstituted fused ring carbazol-9-yl group, and at least R １ is a fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are substituted on the carbon atoms constituting the ring skeleton. ２ ~R ４ each independently represents a group represented by the following general formula (3): 【Chemistry 2】 [In general formula (3), R 11 and R 12 each independently represent a substituent, and the substituent here also includes a deuterium atom. n11 and n12 each independently represent an integer from 0 to 4. One of the carbon atoms constituting the ring skeleton at positions 1 to 4 of the carbazole may be substituted with a nitrogen atom, and one of the carbon atoms constituting the ring skeleton at positions 5 to 8 of the carbazole may be substituted with a nitrogen atom. * represents the bonding position to the benzene ring in general formula (1).]

2. R ２ ~R ４ wherein when one of the groups is a fused carbazol-9-yl group, two or more substituted or unsubstituted aryl groups are substituted on carbon atoms constituting the ring skeleton of the fused carbazol-9-yl group.

3. R １ represents a fused carbazol-9-yl group having two or more substituted or unsubstituted aryl groups substituted on the carbon atoms constituting the ring skeleton, and R ２ ~R ４ The compound according to claim 1 , wherein each independently represents a group represented by general formula (3).

4. The compound according to claim 1, wherein the fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are substituted on carbon atoms constituting the ring skeleton has a fused ring structure of 5 to 7 rings including carbazole.

5. The compound according to claim 1, wherein the fused carbazol-9-yl group in which two or more substituted or unsubstituted aryl groups are substituted on the carbon atoms constituting the ring skeleton has a structure represented by the following general formula (2): 【Transformation 3】 [In the general formula (2), X is O, S, N(R ８ ) or C(R ９ ) (R １０ ) represents. ５ ~R ７ each independently represents a substituent (the substituent includes a deuterium atom); n5 and n7 each independently represent an integer of 0 to 4, and n6 represents an integer of 0 to 2. However, n5 + n6 + n7 is an integer of 2 to 10, and the number of R ５ ~R ７ At least two of R bonded to adjacent carbon atoms constituting the ring skeleton are substituted or unsubstituted aryl groups. ５ R bonded to adjacent ring skeleton carbon atoms ６ R bonded to adjacent ring skeleton carbon atoms ７ may be bonded to each other to form a cyclic structure. * indicates the bonding position to the benzene ring in general formula (1).

6. The compound of claim 5, wherein n5 + n6 + n7 is 2.

7. R ５ One of and R ７ are each independently a substituted or unsubstituted aryl group; R ５ One of and R ６ are each independently a substituted or unsubstituted aryl group; R ６ One of and R ７ and only one of each is independently a substituted or unsubstituted aryl group. The compound of claim 5.

8. A composition comprising the compound according to any one of claims 1 to 7 and a pyrromethene boron complex compound.

9. A light-emitting material comprising the compound according to any one of claims 1 to 7.

10. A delayed fluorescent material comprising the compound according to any one of claims 1 to 7.

11. A film comprising the compound according to any one of claims 1 to 7.

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

13. An organic light-emitting device comprising the compound according to any one of claims 1 to 7.

14. The organic light-emitting device of claim 13 , wherein the device has a layer comprising the compound, the layer also comprising a host material.

15. 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.

16. The organic light-emitting device of claim 14 , 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.

17. The organic light-emitting device according to claim 14 , wherein the compound emits the greatest amount of light among the materials contained in the device.

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

19. The organic light-emitting device according to claim 13, which is an organic electroluminescence device.

20. The organic light-emitting device according to claim 13, which emits delayed fluorescence.

Images