Compound, light-emitting material and light-emitting device

Abstract

To provide a novel compound excellent in light-emitting properties.SOLUTION: A compound of the general formula in the figure is provided, where A represents a 2- or 4-cyanophenyl group or a cyanopyridyl group; one of R2 and R3 represents an acceptor group; the other of R2 and R3 and at least one of R1, R4 and R5 represent a benzofuro- or benzothieno-fused ring carbazol-9-yl group; and the remaining R1 to R5 represent a hydrogen atom, a deuterium atom, an aryl group or a donor group.SELECTED DRAWING: None

Description

[Technical Field]

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

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

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

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

[0005] [ka] [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Chinese Patent Publication No. 112409240 [Non-patent literature]

[0007] [Non-Patent Document 1] Adv.Mater.2020,32,1908355 Summary of the Invention [Problem to be solved by the invention]

[0008] Even among materials that emit delayed fluorescence, those with extremely good properties and no practical problems have not yet been provided. Therefore, it would be useful to provide a delayed fluorescent material with even better luminescence properties than the above-mentioned delayed fluorescent materials. For example, if a light-emitting material with a shorter delayed fluorescence lifetime than the above-mentioned delayed fluorescent materials could be provided, its industrial applicability would be enhanced. However, improvements to delayed fluorescent materials are still in the trial and error stage, and it is not easy to generalize the chemical structure of a useful light-emitting material.

[0009] Under these circumstances, the present inventors have conducted extensive research with the aim of providing compounds that are more useful as light-emitting materials for light-emitting devices, and have conducted extensive research with the aim of deriving and generalizing a general formula for compounds that are more useful as light-emitting materials. [Means for solving the problem]

[0010] As a result of intensive research to achieve the above object, the present inventors have found that compounds having a structure that satisfies certain conditions are useful as light-emitting materials. The present invention has been proposed based on this finding, and specifically has the following configurations.

[0011] [1] A compound represented by the following general formula (1): [ka] [In general formula (1), A represents a 2-cyanophenyl group, a 4-cyanophenyl group, or a cyanopyridyl group which may be substituted with a phenyl group or a naphthyl group, and the hydrogen atoms of these groups may be substituted with deuterium atoms. R 2 and R 3 One of R represents an acceptor group. 2 and R 3 On the other hand, R 1 , R 4 , R 5 At least one of R independently represents a substituted or unsubstituted benzofuro-fused carbazol-9-yl group or a substituted or unsubstituted benzothieno-fused carbazol-9-yl group. 1 ~R 5 each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or a donor group (however, the donor group does not include an alkyl group, a substituted or unsubstituted benzofuro-fused carbazol-9-yl group, or a substituted or unsubstituted benzothieno-fused carbazol-9-yl group). [2] The compound according to [1], having a maximum emission wavelength in the range of 420 nm to 575 nm. [3] R 2 is an acceptor group. [4] R 3 is an acceptor group. [5] The compound according to any one of [1] to [4], wherein the acceptor group has the same structure as A. [6] The compound according to any one of [1] to [5], wherein the acceptor group is a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom, or a cyano group. [7] R 1 ~R 5The compound according to any one of [1] to [6], wherein at least two of the above are each independently a substituted or unsubstituted benzofuro-fused carbazol-9-yl group or a substituted or unsubstituted benzothieno-fused carbazol-9-yl group. [8] R 2 and R 5 The compound according to any one of [1] to [7], wherein each independently represents a donor group. [9] The compound according to any one of [1] to [8], wherein the donor group is a substituted or unsubstituted diarylamino group (wherein the two aryl groups constituting the diarylamino group may be bonded to each other).

[10] The compound according to any one of [1] to [9], which has a symmetric structure.

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

[10] .

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

[10] .

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

[10] .

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

[10] .

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

[10] .

[16] The organic light-emitting device according to

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

[17] The organic light-emitting element according to

[16] , 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.

[18] The organic light-emitting device according to

[16] , 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.

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

[16] to

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

[20] The organic light-emitting element according to

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

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

[15] to

[20] , which is an organic electroluminescence device.

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

[15] to

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

[0012] The compound represented by general formula (1) has excellent light-emitting properties. General formula (1) includes a light-emitting material that emits deep blue light. General formula (1) also includes a light-emitting material that exhibits a short delayed fluorescence lifetime. By using the compound represented by general formula (1), an excellent organic light-emitting device can be provided. DETAILED DESCRIPTION OF THE INVENTION

[0013] The present invention will be described in detail below. The following description of the constituent elements may be based on typical embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, a numerical range expressed using "to" means a range that includes the numerical values ​​before and after "to" as the lower and upper limits. In addition, some or all of the hydrogen atoms present in the molecules of the compound used in the present invention may be replaced with deuterium atoms ( 2 In the chemical structural formulas herein, hydrogen atoms are represented by H or are omitted. For example, when the atom bonded to a carbon atom constituting the ring skeleton of a benzene ring is omitted, H is assumed to be bonded to the carbon atom constituting the ring skeleton at the omitted position. In the chemical structural formulas herein, deuterium atoms are represented by D.

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

[0015] In general formula (1), A represents a 2-cyanophenyl group, a 4-cyanophenyl group, or a cyanopyridyl group optionally substituted with a phenyl group or a naphthyl group. The hydrogen atoms of the 2-cyanophenyl group and the 4-cyanophenyl group may be substituted with deuterium atoms, but are not substituted with any other atoms or groups. In one embodiment of the present invention, A is a 2-cyanophenyl group. In a preferred embodiment of the present invention, A is a 4-cyanophenyl group. The bonding position of the cyano group of the cyanopyridyl group represented by A may be any of the 2- to 4-positions of the pyridine ring. In a preferred embodiment of the present invention, the 2-position of the pyridine ring is a cyano group. In another embodiment of the present invention, the 3-position of the pyridine ring is a cyano group. In another embodiment of the present invention, the 4-position of the pyridine ring is a cyano group. The bonding site of the cyanopyridyl group may be any of the 2- to 6-positions of the pyridine ring. Each hydrogen atom of the cyanopyridyl group represented by A may be independently substituted with one or more atoms or groups selected from the group consisting of deuterium atoms, phenyl groups, and naphthyl groups. Some or all of the phenyl groups may be substituted with deuterium atoms. Some or all of the naphthyl groups may also be substituted with deuterium atoms. In one embodiment of the present invention, the cyanopyridyl group is substituted with at least one phenyl group. In another embodiment of the present invention, the cyanopyridyl group is substituted with at least one naphthyl group. In one preferred embodiment of the invention, the cyanopyridyl group is not substituted with a phenyl or naphthyl group. In one embodiment of the present invention, A has at least one deuterium atom. In one embodiment of the present invention, all hydrogen atoms present in the 2-cyanophenyl group, 4-cyanophenyl group, and cyanopyridyl group optionally substituted with a phenyl group or a naphthyl group represented by A are substituted with deuterium atoms.

[0016] Specific examples of groups that can be used for A in general formula (1) are shown below. However, A 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 C6D5 represents a phenyl group in which all hydrogen atoms are deuterated.

[0017] [ka] JPEG0007752866000005.jpg240170JPEG0007752866000006.jpg227170JPEG0007752866000007.jpg112170

[0018] The compounds obtained by substituting all hydrogen atoms present in the above A1 to A95 with deuterium atoms are disclosed as A1(D) to A95(D). In a preferred embodiment of the present invention, A in general formula (1) is selected from the group consisting of A1 to A95. In one embodiment of the present invention, A is selected from the group consisting of A78 to A95 and A1(D) to A95(D). In one embodiment of the present invention, A is selected from the group consisting of A3 to A95. In one embodiment of the present invention, A is selected from the group consisting of A3 to A14. In one embodiment of the present invention, A is selected from the group consisting of A15 to A95. In one embodiment of the present invention, A is selected from the group consisting of A3 to A6, A15 to A32, and A78 to A82. In one embodiment of the present invention, A is selected from the group consisting of A7 to A10, A33 to A59, and A83 to A91. In one embodiment of the present invention, A is selected from the group consisting of A11 to A14, A60 to 77, and A92 to 95.

[0019] In general formula (1), R 2 and R 3 In one embodiment of the present invention, one of R 2 is an acceptor group. In one embodiment of the present invention, R 3 is an acceptor group. R 2 and R 3The acceptor group that can be taken by R may be a 2-cyanophenyl group, a 4-cyanophenyl group, or a cyanopyridyl group that may be substituted with a phenyl group or a naphthyl group (the hydrogen atoms of these groups may be substituted with deuterium atoms). For the description and preferred range of these groups, please refer to the description of A above. In a preferred embodiment of the present invention, the acceptor group is the same group as A. In this case, when A and R 2 are the same group, or A and R 3 are the same group. In one aspect of the present invention, R 2 and R 3 is a 2-cyanophenyl group, a 4-cyanophenyl group, or a cyanopyridyl group optionally substituted with a phenyl group or a naphthyl group (the hydrogen atoms of these groups may be substituted with deuterium atoms), but is a group different from A. In one aspect of the present invention, R 2 and R 3 One of the groups is an acceptor group, but is not a 2-cyanophenyl group, a 4-cyanophenyl group, or a cyanopyridyl group optionally substituted with a phenyl group or a naphthyl group (the hydrogen atoms of these groups may be substituted with deuterium atoms). Such an acceptor group can be selected from groups having a positive Hammett σp value. The Hammett σp value was proposed by L.P. Hammett and quantifies the effect of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, the following equation holds between the substituent in a para-substituted benzene derivative and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp or log(K / K0) = ρσp where k is the rate constant for a benzene derivative having no substituent, k is the rate constant for a benzene derivative substituted with a substituent, K is the equilibrium constant for a benzene derivative having no substituent, K is the equilibrium constant for a benzene derivative substituted with a substituent, and ρ is a reaction constant determined by the type and conditions of the reaction. For an explanation of the "Hammett σp value" in the present invention and the numerical values ​​of each substituent, please refer to the description of the σp value in Hansch, C. et al., Chem. Rev., 91, 165-195 (1991). R 2 and R 3 The acceptor group that can be one of the above preferably has a σp of 0.3 or more, more preferably 0.5 or more, and even more preferably 0.7 or more. For example, it may be selected from the range of 0.9 or more, or from the range of 1.1 or more.

[0020] Examples of acceptor groups other than 2-cyanophenyl groups, 4-cyanophenyl groups, and cyanopyridyl groups optionally substituted with phenyl or naphthyl groups (the hydrogen atoms of these groups may be substituted with deuterium atoms) include cyano groups. Other typical acceptor groups include heteroaryl groups containing two or more nitrogen atoms as ring skeleton-constituting atoms. Examples include triazinyl groups and pyrimidinyl groups. The hydrogen atoms of these heteroaryl groups may be substituted with deuterium atoms or substituents. The substituents may be selected from, for example, substituent group E, and include, for example, unsubstituted aryl groups, preferably unsubstituted phenyl groups.

[0021] Specific examples of groups that can be used as the acceptor group in general formula (1) include A1 to A95 and A1(D) to A95(D) above. Other typical examples of acceptor groups include those listed below. However, the acceptor 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 the bonding position, and C6D5 represents a phenyl group in which all hydrogen atoms are deuterated.

[0022] [ka]

[0023] In general formula (1), R 2 and R 3 the other (i.e., the non-acceptor group), R 1 , R 4 , R 5 At least one of R independently represents a substituted or unsubstituted benzofuro-fused carbazol-9-yl group or a substituted or unsubstituted benzothieno-fused carbazol-9-yl group (hereinafter, these are collectively referred to as "fused carbazol-9-yl groups"). 1 ~R 5 Among these, the number of fused carbazol-9-yl groups is 1 to 4, for example, 1 to 3, for example, 1 or 2. The number of fused carbazol-9-yl groups may be 2 to 4, or may be 2 or 3. In one group of the present invention, R 3 is an acceptor group, and R 1 , R 2 , R 4 , R 5 In one embodiment of the present invention, at least one of R 2 is a fused carbazol-9-yl group. 2 In a preferred embodiment of the present invention, only R 2 and R 5is a fused carbazol-9-yl group. In a preferred embodiment of the present invention, R 2 and R 5 In a preferred embodiment of the present invention, only R 2 , R 4 , R 5 is a fused carbazol-9-yl group. 1 ~R 4 is a fused carbazol-9-yl group. In another group of the invention, R 2 is an acceptor group, and R 1 , R 3 , R 4 , R 5 In one embodiment of the present invention, at least one of R 1 is a fused carbazol-9-yl group. 3 is a fused carbazol-9-yl group. 4 is a fused carbazol-9-yl group. 5 is a fused carbazol-9-yl group. 3 In one embodiment of the present invention, only R 4 In one embodiment of the present invention, only R 5 In a preferred embodiment of the present invention, only R 3 and R 5 is a fused carbazol-9-yl group. 3 and R 4 is a fused carbazol-9-yl group. 4 and R 5 is a fused carbazol-9-yl group. In a preferred embodiment of the present invention, R 3 and R 5 In a preferred embodiment of the present invention, only R 3 ~R 5 is a fused carbazol-9-yl group.1 , R 3 , R 4 , R 5 is a fused carbazol-9-yl group. When multiple fused carbazol-9-yl groups are present, in a preferred embodiment of the present invention, the fused carbazol-9-yl groups are the same. In one embodiment of the present invention, the fused carbazol-9-yl groups are different from each other. In a preferred embodiment of the present invention, the fused carbazol-9-yl group is a benzofuro-fused carbazol-9-yl group. In one embodiment of the present invention, the fused carbazol-9-yl group is a benzhieno-fused carbazol-9-yl group.

[0024] In the present invention, as the benzofuro-fused carbazol-9-yl group, a benzofuro[2,3-a]carbazol-9-yl group can be used. A benzofuro[3,2-a]carbazol-9-yl group can also be used. A benzofuro[2,3-b]carbazol-9-yl group can also be used. A benzofuro[3,2-b]carbazol-9-yl group can also be used. A benzofuro[2,3-c]carbazol-9-yl group can also be used. A benzofuro[3,2-c]carbazol-9-yl group can also be used. A preferred benzofuro-fused carbazol-9-yl group is a carbazol-9-yl group having only one benzofuran ring fused at the 2- and 3-positions and no other rings fused thereto. Specifically, it is a group having any of the following structures, in which at least one hydrogen atom in the following structure may be substituted: [ka]

[0025] In the present invention, as the benzothieno-fused carbazol-9-yl group, a benzothieno[2,3-a]carbazol-9-yl group can be used. 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. A preferred benzoeno-fused carbazol-9-yl group is a carbazol-9-yl group having only one benzothiophene ring fused at the 2- and 3-positions and no other rings fused thereto. Specifically, it is a group having any of the following structures, in which at least one hydrogen atom in the following structure may be substituted: [ka]

[0026] The substituent of the fused carbazol-9-yl group may be selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In a preferred embodiment of the present invention, the fused carbazol-9-yl group is unsubstituted. In a preferred embodiment of the present invention, the substituent of the fused carbazol-9-yl group is substituted with an unsubstituted aryl group. In one embodiment of the present invention, the substituent of the fused carbazol-9-yl group is substituted with an unsubstituted alkyl group. 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 from, for example, Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In one embodiment of the present invention, the substituent of the aryl group is one or more selected from the group consisting of an alkyl group, an aryl group, and a deuterium atom. In a preferred embodiment of the present invention, the aryl group is unsubstituted. The "alkyl group" may be linear, branched, or cyclic. It may also contain two or more of the linear, cyclic, and branched groups. 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 methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, 2-ethylhexyl, n-heptyl, isoheptyl, n-octyl, isooctyl, n-nonyl, isononyl, n-decanyl, isodecanyl, cyclopentyl, cyclohexyl, and cycloheptyl. The alkyl group may be further substituted with, for example, a deuterium atom, an aryl group, an alkoxy group, an aryloxy group, or a halogen atom. In one embodiment of the present invention, the substituents on the alkyl group are one or more selected from the group consisting of an aryl group and a deuterium atom. In a preferred embodiment of the present invention, the alkyl group is unsubstituted. The number of substituents substituted on the ring-fused carbazol-9-yl group is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4, and may be, for example, 1 or 2. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group is substituted at either the 3- or 6-position. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has at least one substituent at the para-position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has at least one substituent only at the para-position of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group. In a preferred embodiment of the present invention, the ring-fused carbazol-9-yl group has substituents at all substitutable para-positions of the benzene ring relative to the heteroatom present in the ring-fused carbazol-9-yl group.

[0027] Specific examples of substituted or unsubstituted benzofuro-fused carbazol-9-yl groups or substituted or unsubstituted benzothieno-fused carbazol-9-yl groups (i.e., fused carbazol-9-yl groups) that can be employed in general formula (1) are shown below. However, the fused carbazol-9-yl 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, Ph represents a phenyl group, and C6D5 represents a phenyl group in which all hydrogen atoms are deuterated. Methyl groups are omitted. Therefore, for example, D7 to D18 have methyl groups.

[0028] [ka] JPEG0007752866000012.jpg247170JPEG0007752866000013.jpg249170JPEG0007752866000014.jpg220168JPEG000 7752866000015.jpg255169JPEG0007752866000016.jpg222170JPEG0007752866000017.jpg229164JPEG0007752866 000018.jpg243170JPEG0007752866000019.jpg233164JPEG0007752866000020.jpg228163JPEG0007752866000021. jpg255167JPEG0007752866000022.jpg244170JPEG0007752866000023.jpg226170JPEG0007752866000024.jpg21317 0JPEG0007752866000025.jpg248158JPEG0007752866000026.jpg227170JPEG0007752866000027.jpg225170JPEG00 07752866000028.jpg253170JPEG0007752866000029.jpg243170JPEG0007752866000030.jpg201170JPEG0007752866 000031.jpg235164JPEG0007752866000032.jpg222170JPEG0007752866000033.jpg248170JPEG0007752866000034. jpg239166JPEG0007752866000035.jpg221170JPEG0007752866000036.jpg253170JPEG0007752866000037.jpg53163

[0029] The above D1 to D459 in which all hydrogen atoms have been replaced with deuterium atoms are disclosed as D1(D) to D459(D). In one aspect of the present invention, R in general formula (1) 1 ~R 5 In one embodiment of the present invention, the fused carbazol-9-yl group R in general formula (1) is selected from the group consisting of D1 to D459.1 ~R 5 In one embodiment of the present invention, the fused carbazol-9-yl group R in general formula (1) is selected from the group consisting of D1 to D30. 1 ~R 5 In one embodiment of the present invention, the fused carbazol-9-yl group R in general formula (1) is selected from the group consisting of D31 to D60. 1 ~R 5 In one embodiment of the present invention, the fused carbazol-9-yl group R in general formula (1) is selected from the group consisting of D61 to D84. 1 ~R 5 The fused carbazol-9-yl group that can be taken by R is selected from the group consisting of D88 to D91, D95 to D198, D287 to D293, D306 to D317, and D330 to D459. 1 ~R 5 The fused carbazol-9-yl group that can be taken by R is selected from the group consisting of D92, D93, and D199 to D286. 1 ~R 5 The fused carbazol-9-yl group that can be taken by is selected from the group consisting of D294 to D459.

[0030] The remaining R in general formula (1) 1 ~R 5 each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or a donor group (however, the donor group referred to here does not include an alkyl group, a substituted or unsubstituted benzofuro-fused carbazol-9-yl group, or a substituted or unsubstituted benzothieno-fused carbazol-9-yl group). 1 ~R 5 " means neither an acceptor group, a substituted or unsubstituted benzofuro-fused carbazol-9-yl group, nor a substituted or unsubstituted benzothieno-fused carbazol-9-yl group. Remaining R 1 ~R 5 The number of R is 0 to 3. In one embodiment of the present invention, the remaining R 1 ~R 5are hydrogen atoms or deuterium atoms. In one embodiment of the present invention, the remaining R 1 ~R 5 comprises a substituted or unsubstituted aryl group. In one aspect of the invention, the remaining R 1 ~R 5 In one embodiment of the present invention, the remaining R 1 ~R 5 In one embodiment of the present invention, the remaining R 1 ~R 5 is a hydrogen atom, a deuterium atom, or a donor group. 1 ~R 5 are hydrogen atoms, deuterium atoms, or substituted or unsubstituted aryl groups. In one embodiment of the present invention, the remaining R 1 ~R 5 contains a deuterium atom.

[0031] Remaining R 1 ~R 5 For the description and preferred range of the substituted or unsubstituted aryl group that may be taken by R, the description and preferred range of the aryl group as a substituent of the fused ring-fused carbazol-9-yl group can be referred to. 1 ~R 5 The substituted or unsubstituted aryl group which can be taken by is an unsubstituted aryl group, preferably an unsubstituted phenyl group. However, the remaining R 1 ~R 5 The aryl group which can be taken is not substituted with a cyano group.

[0032] Remaining R 1 ~R 5 The donor group that can be taken by can be selected from groups with a negative Hammett σp value. 1 ~R 5 The donor group preferably has a σp of −0.3 or less, more preferably −0.5 or less, and even more preferably −0.7 or less, and may be selected, for example, from the range of −0.9 or less, or from the range of −1.1 or less. Remaining R 1 ~R 5When the number of donor groups is two or more, it is preferable that all of the donor groups are the same. In one embodiment of the present invention, the two or more donor groups are different from each other. Remaining R 1 ~R 5 The donor group that can be used is preferably a group containing a substituted amino group. It may be a substituted amino group, or an aryl group to which a substituted amino group is bonded, particularly a phenyl group to which a substituted amino group is bonded. In a preferred embodiment of the present invention, the donor group is a substituted amino group. The substituent bonded to the nitrogen atom of the substituted amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and more preferably a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. The substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group. The two aryl groups constituting the diarylamino group may be bonded to each other, or the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other. For the descriptions and preferred ranges of the aryl group and alkyl group referred to herein, please refer to the descriptions and preferred ranges of the aryl group and alkyl group as substituents of the fused carbazol-9-yl group described above. The "heteroaryl group" referred to herein may be a monocyclic ring or a fused ring in which two or more rings are fused. When the heteroaryl group is a fused ring, the number of fused rings is preferably 2 to 6, and can be selected from, for example, 2 to 4. Specific examples of the ring include a pyridine ring and a pyrimidine ring, and these rings may be fused with another ring. Specific examples of the heteroaryl group include a 2-pyridyl group, a 3-pyridyl group, and a 4-pyridyl group. The number of atoms constituting the ring skeleton of the heteroaryl group is preferably 4 to 40, more preferably 5 to 20, and may be selected from the range of 5 to 14, or may be selected from the range of 5 to 10.

[0033] Remaining R1 ~R 5 The donor group that can be used is preferably a substituted or unsubstituted carbazol-9-yl group (excluding substituted or unsubstituted benzofuro-fused carbazol-9-yl groups and substituted or unsubstituted benzothieno-fused carbazol-9-yl groups). In one embodiment of the present invention, a further benzene ring may be fused to the two benzene rings that constitute the carbazol-9-yl group. In one embodiment of the present invention, a further pyridine ring may be fused to the two benzene rings that constitute the carbazol-9-yl group. In one embodiment of the present invention, at least one of the ring carbon atoms that constitute the carbazol-9-yl group is substituted with a nitrogen atom. When substituted, it is preferable that one ring carbon atom per benzene ring is substituted with a nitrogen atom. It is also preferable that one ring carbon atom is substituted with a nitrogen atom in the entire donor group. The substituents of the carbazol-9-yl group may be selected from Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E. In a preferred embodiment of the present invention, the remaining R 1 ~R 5 The carbazol-9-yl group represented by the formula (I) may be a fused ring, but the hydrogen atom is not substituted. In a preferred embodiment of the present invention, the fused ring-containing carbazol-9-yl group is substituted with an unsubstituted aryl group. In another embodiment of the present invention, the fused ring-containing carbazol-9-yl group is substituted with an unsubstituted alkyl group.

[0034] In the following, the remaining R 1 ~R 5 Specific examples of donor groups that can be used are shown below. However, the donor groups that can be used in the present invention should not be construed as being limited by the following specific examples. In the following specific examples, * indicates the bonding position. Methyl groups are not shown, so for example, Z2 has one methyl group. [ka] JPEG0007752866000039.jpg82170

[0035] The above Z1 to Z36 each have all hydrogen atoms replaced with deuterium atoms and are disclosed as Z1(D) to Z36(D). In one embodiment of the present invention, the remaining R 1 ~R 5 The donor group that can be taken by Z1 to Z36 is selected from the group consisting of Z1 to Z36. 1 ~R 5 In one embodiment of the present invention, the remaining R in general formula (1) is selected from the group consisting of Z1 to Z6. 1 ~R 5 The donor group which can be taken by is selected from the group consisting of Z7 to Z36.

[0036] R in general formula (1) 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 do not bond to each other to form a ring structure. In a preferred embodiment of the present invention, the compound represented by general formula (1) has a symmetric structure. For example, the compound represented by general formula (1) has a linear symmetric structure. For example, the compound represented by general formula (1) has a rotationally symmetric structure. In one embodiment of the present invention, the compound represented by general formula (1) has an asymmetric structure.

[0037] In one embodiment of the present invention, the compound represented by general formula (1) contains at least one deuterium atom. In one embodiment of the present invention, it has a deuterated alkyl group (e.g., a deuterated methyl group, a deuterated ethyl group, or a deuterated cyclohexyl group). In one embodiment of the present invention, it has a deuterated aryl group (e.g., a deuterated phenyl group). In one embodiment of the present invention, all hydrogen atoms are deuterated.

[0038] The compound represented by general formula (1) preferably does not contain metal atoms, and may be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, oxygen, and sulfur atoms. In a preferred embodiment of the present invention, the compound represented by general formula (1) is composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, and oxygen atoms. The compound represented by general formula (1) may also be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, and sulfur atoms. The compound represented by general formula (1) may also be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, deuterium, and nitrogen atoms. The compound represented by general formula (1) may also be a compound composed only of atoms selected from the group consisting of carbon, hydrogen, and nitrogen atoms. Furthermore, the compound represented by general formula (1) may not contain hydrogen atoms, but may contain deuterium atoms.

[0039] In the present specification, "substituent group A" refers to a hydroxyl group, a halogen atom (for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom), an alkyl group (for example, having 1 to 40 carbon atoms), an alkoxy group (for example, having 1 to 40 carbon atoms), an alkylthio group (for example, having 1 to 40 carbon atoms), an aryl group (for example, having 6 to 30 carbon atoms), an aryloxy group (for example, having 6 to 30 carbon atoms), an arylthio group (for example, having 6 to 30 carbon atoms), a heteroaryl group (for example, having 5 to 30 ring skeleton atoms), a heteroaryloxy group (for example, having 5 to 30 ring skeleton atoms), a heteroaryl group, ... It means one group or a combination of two or more groups selected from the group consisting of heteroarylthio groups (for example, having 5 to 30 atoms constituting the ring skeleton), acyl groups (for example, having 1 to 40 carbon atoms), alkenyl groups (for example, having 1 to 40 carbon atoms), alkynyl groups (for example, having 1 to 40 carbon atoms), alkoxycarbonyl groups (for example, having 1 to 40 carbon atoms), aryloxycarbonyl groups (for example, having 1 to 40 carbon atoms), heteroaryloxycarbonyl groups (for example, having 1 to 40 carbon atoms), silyl groups (for example, trialkylsilyl groups having 1 to 40 carbon atoms), and nitro groups. In this specification, the term "substituent group B" refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 40 carbon atoms), alkoxy groups (e.g., having 1 to 40 carbon atoms), aryl groups (e.g., having 6 to 30 carbon atoms), aryloxy groups (e.g., having 6 to 30 carbon atoms), heteroaryl groups (e.g., having 5 to 30 ring skeleton atoms), heteroaryloxy groups (e.g., having 5 to 30 ring skeleton atoms), and diarylaminoamino groups (e.g., having 0 to 20 carbon atoms). In this specification, the term "substituent group C" refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups (e.g., having 6 to 22 carbon atoms), heteroaryl groups (e.g., having 5 to 20 ring skeleton atoms), and diarylamino groups (e.g., having 12 to 20 carbon atoms). In this specification, the term "substituent group D" refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups (e.g., having 6 to 22 carbon atoms), and heteroaryl groups (e.g., having 5 to 20 ring skeleton atoms). In this specification, the term "substituent group E" refers to one group or a combination of two or more groups selected from the group consisting of alkyl groups (for example, having 1 to 20 carbon atoms) and aryl groups (for example, having 6 to 22 carbon atoms). In the present specification, when a "substituent" or "substituted or unsubstituted" is used, the substituent may be selected from, for example, Substituent Group A, Substituent Group B, Substituent Group C, Substituent Group D, or Substituent Group E.

[0040] Specific examples of the compound represented by general formula (1) are shown in Tables 1 and 2 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 Tables 1 and 2, the compounds represented by A and R in general formula (1) are 1 ~R 5 The structures of compounds 1 to 24786 are shown individually by specifying each compound.

[0041] In Table 2, Ph represents a phenyl group. In Table 2, each row contains A and R of multiple compounds. 1 ~R 5 The structures of compounds 1 to 24786 are shown by displaying all of these together. For example, in the column for compounds 1 to 459 in Table 2, A and R 3 A1, R 1 and R 4 is fixed at Z1, and R 2 and R 5 The compounds D1 to D459 with the same A and R are designated as compounds 1 to 459 in order. That is, the column of compounds 1 to 459 in Table 2 collectively displays compounds 1 to 459 identified in Table 1. Similarly, in the column of compounds 460 to 918 in Table 2, A and R 3 A1, R 1 and R 4 is fixed to Z6, and R 2 and R 5 Compounds D1 to D459 with the same structure are designated as compounds 460 to 918. Compounds 919 to 8262 in Table 2 are also identified in the same manner. Compounds 8263 to 16524 in Table 2 are R 3 and R 5 For example, in the column of compounds 8263 to 8721 in Table 2, A and R 2 A1, R 1 is a hydrogen atom (H), R 4 is fixed at Z1, and R 3 and R 5 Compounds D1 to D459 with the same structure are designated as compounds 8263 to 8721, respectively. Compounds 16525 to 20655 in Table 2 are R 3 ~R 5 For example, in the column of compounds 16525 to 16983 in Table 2, A and R 2 A1, R 1 is fixed to a hydrogen atom (H), and R 3 ~R 5Compounds D1 to D459 with the same structure are designated as compounds 16525 to 16983, respectively. Compounds 20656 to 24786 in Table 2 are R 3 and R 5 For example, in the column of compounds 20656 to 21114 in Table 2, A and R 2 A1, R 1 is a hydrogen atom (H), R 4 is fixed to the phenyl group (Ph), and R 3 and R 5 Compounds D1 to D459 with the same structure are designated as compounds 20656 to 21114, respectively. [Table 1] JPEG0007752866000041.jpg235161JPEG0007752866000042.jpg236161JPEG0007752866000043.jpg23416 0JPEG0007752866000044.jpg239163JPEG0007752866000045.jpg239163JPEG0007752866000046.jpg9656 [Table 2] JPEG0007752866000048.jpg55164

[0042] Compounds 1(D) to 24786(D) are disclosed as compounds obtained by substituting all hydrogen atoms present in the molecules of the above compounds 1 to 24786 with deuterium atoms. 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.

[0043] In one embodiment of the present invention, a compound is selected from compounds 1 to 24786. In one embodiment of the present invention, a compound is selected from compounds 1(D) to 24786(D). In one embodiment of the present invention, a compound is selected from compounds 1 to 1324. In one embodiment of the present invention, a compound is selected from compounds 1325 to 2648. In one embodiment of the present invention, a compound is selected from compounds 2649 to 3972. In one embodiment of the present invention, a compound is selected from compounds 3973 to 5296. In one embodiment of the present invention, a compound is selected from compounds 1 to 8262. In one embodiment of the present invention, a compound is selected from compounds 8263 to 16524. In one embodiment of the present invention, a compound is selected from compounds 16525 to 20655. In one embodiment of the present invention, a compound is selected from compounds 20656 to 24786. In one embodiment of the present invention, the compounds are selected from compounds 1 to 918, 2755 to 3672, 5509 to 6426, 8263 to 9180, 11017 to 11934, 13771 to 14688, 16525 to 16983, 17902 to 18360, 19279 to 19737, 20656 to 21114, 22033 to 22491, and 23410 to 23868. In one embodiment of the present invention, the compounds are selected from compounds 919 to 2754, 3673 to 5508, 6427 to 8262, 9181 to 11016, 11935 to 13770, 14689 to 16524, 16984 to 17901, 18361 to 19278, 19738 to 20655, 21115 to 22032, 22492 to 23409, and 23869 to 24786.

[0044] In a preferred embodiment of the present invention, the compound represented by general formula (1) is selected from the following group of compounds: [ka]

[0045] When it is intended to use an organic layer containing the compound represented by general formula (1) formed by vapor deposition, the molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 900 or less. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by general formula (1). The compound represented by general formula (1) may be formed into a film by a coating method regardless of its molecular weight. By using the coating method, it is possible to form a film even from a compound with a relatively large molecular weight. The compound represented by general formula (1) has the advantage of being easily soluble in organic solvents. Therefore, the compound represented by general formula (1) is easy to apply the coating method to, and is also easy to purify to increase its purity.

[0046] It is also conceivable that the present invention can be applied to use a compound containing a plurality of structures represented by general formula (1) in the molecule as a light-emitting material. For example, a polymerizable group may be pre-existed in the structure represented by general formula (1), and the polymer obtained by polymerizing the polymerizable group may be used as a light-emitting material. For example, a monomer containing a polymerizable functional group at any site of general formula (1) may be prepared, and the monomer may be polymerized alone or copolymerized with other monomers to obtain a polymer having repeating units, and the polymer may be used as a light-emitting material. Alternatively, compounds having a structure represented by general formula (1) may be coupled to obtain dimers or trimers, and these may be used as light-emitting materials.

[0047] Examples of polymers having a repeating unit containing a structure represented by general formula (1) include polymers containing a structure represented by either of the following two general formulas. [ka]

[0048] In the above general formula, Q represents a group containing a structure represented by general formula (1), and L 1 and L 2 represents a linking group. The number of carbon atoms in the linking group is preferably 0 to 20, more preferably 1 to 15, and even more preferably 2 to 10. The linking group is -X 11 -L 11 Preferably, X has a structure represented by the formula: 11represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. 11 represents a linking group, which is preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, and more preferably a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms or a substituted or unsubstituted phenylene group. In the above general formula, R 101 , R 102 , R 103 and R 104 each independently represents a substituent, preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom, and still more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, or an unsubstituted alkoxy group having 1 to 3 carbon atoms. L 1 and L 2 The linking group represented by the following formula can be bonded to any site of general formula (1) constituting Q. Two or more linking groups may be bonded to one Q to form a crosslinked structure or a network structure.

[0049] Specific structural examples of the repeating unit include structures represented by the following formulas. [ka]

[0050] A polymer having repeating units containing these formulae can be synthesized by introducing a hydroxy group into any site of general formula (1), reacting the hydroxy group as a linker with the following compound to introduce a polymerizable group, and polymerizing the polymerizable group. [ka]

[0051] A polymer containing a structure represented by general formula (1) in its molecule may be a polymer consisting only of repeating units having the structure represented by general formula (1), or may be a polymer containing repeating units having other structures. The repeating units having the structure represented by general formula (1) contained in the polymer may be of a single type, or may be of two or more types. Examples of repeating units not having the structure represented by general formula (1) include those derived from monomers used in ordinary copolymerization. For example, repeating units derived from monomers having an ethylenically unsaturated bond, such as ethylene and styrene, can be mentioned.

[0052] In some embodiments, the compound represented by general formula (1) is a light-emitting material. In one embodiment, the compound represented by general formula (1) is a compound capable of emitting delayed fluorescence. In certain embodiments of the present disclosure, the compound represented by general formula (1) can emit light in the UV region, the blue region (e.g., about 420 nm to about 500 nm, particularly 420 nm to 480 nm) and the green region (e.g., about 490 nm to about 575 nm, about 510 nm) of the visible spectrum when excited by thermal or electronic means. In one aspect of the present invention, the maximum emission wavelength is in the range of 530 nm to 575 nm. In one aspect of the present invention, the maximum emission wavelength is in the range of 480 nm to 530 nm. In one aspect of the present invention, the maximum emission wavelength is in the range of 460 nm to 480 nm. In one aspect of the present invention, the maximum emission wavelength is in the range of 440 nm to 460 nm. In one aspect of the present invention, the maximum emission wavelength is in the range of 420 nm to 440 nm. In certain embodiments of the present disclosure, compounds represented by general formula (1) are capable of emitting light in the ultraviolet spectral region (e.g., 280-400 nm) when excited by thermal or electronic means. In one embodiment of the present disclosure, an organic semiconductor device can be fabricated using a compound represented by general formula (1). The organic semiconductor device referred to here may be an organic optical device in which light is mediated, or an organic device in which light is not mediated. The organic optical device may be an organic light-emitting device that emits light, an organic light-receiving device that receives light, or an element in which light-mediated energy transfer occurs within the device. In one embodiment of the present disclosure, an organic optical device such as an organic electroluminescence device or a solid-state imaging device (e.g., a CMOS image sensor) can be fabricated using a compound represented by general formula (1). In one embodiment of the present disclosure, a CMOS (complementary metal-oxide semiconductor) can be fabricated using a compound represented by general formula (1).

[0053] The electronic properties of small molecule chemical libraries can be calculated using well-known ab initio quantum chemical calculations. For example, the Hartree-Fock equations can be solved using time-dependent density functional theory (TD-DFT / B3LYP / 6-31G*) with a basis set of functions known as 6-31G*, Becke's three-parameter, and Lee-Yang-Parr hybrid functionals to screen for molecular fragments (moieties) with HOMOs above a certain threshold and LUMOs below a certain threshold. Thus, the donor moiety ("D") can be selected for its HOMO energy (e.g., ionization potential) of, for example, -6.5 eV or greater, and the acceptor moiety ("A") can be selected for its LUMO energy (e.g., electron affinity) of, for example, -0.5 eV or less. The bridging moiety ("B") prevents overlap between the π-conjugated systems of the donor and acceptor moieties, for example, by providing a strongly conjugated system that tightly restricts the acceptor and donor moieties to specific configurations. In some embodiments, the compound library is screened using one or more of the following properties: 1. Emission around a specific wavelength 2. Calculated triplet states above a specific energy level 3. Delta E below a certain value STvalue 4. Quantum yield above a certain value 5.HOMO level 6.LUMO level In one embodiment, the difference between the lowest singlet excited state and the lowest triplet excited state at 77 K (ΔE ST ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In some embodiments, ΔE ST The value is less than about 0.09 eV, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 eV, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.01 eV. In certain embodiments, the compounds represented by general formula (1) exhibit a quantum yield of greater than 25%, e.g., about 30%, about 35%, about 40%, about 45%, about 50%, about 55%, about 60%, about 65%, about 70%, about 75%, about 80%, about 85%, about 90%, about 95% or more.

[0054] [Method for synthesizing the compound represented by general formula (1)] The compounds represented by general formula (1) include novel compounds. The compound represented by general formula (1) can be synthesized by combining known reactions. For example, 1 By reacting benzene having an acceptor group with benzofuro-fused carbazole or benzothieno-fused carbazole, a compound of general formula (1) having a benzofuro-fused carbazol-9-yl group or a benzothieno-fused carbazol-9-yl group can be synthesized. For details of the reaction conditions, please refer to the synthesis examples described below.

[0055] [Constructs using compounds represented by general formula (1)] In some embodiments, the compounds of Formula (1) may be combined with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) that disperse, covalently bond, coat, support, or associate with the compounds to form a solid film or layer. For example, the compounds of Formula (1) may be combined with an electroactive material to form a film. In some cases, the compounds of Formula (1) may be combined with a hole transporting polymer. In some cases, the compounds of Formula (1) may be combined with an electron transporting polymer. In some cases, the compounds of Formula (1) may be combined with a hole transporting polymer and an electron transporting polymer. In some cases, the compounds of Formula (1) may be combined with a copolymer having both a hole transporting moiety and an electron transporting moiety. In these embodiments, electrons and / or holes formed in the solid film or layer may interact with the compounds of Formula (1).

[0056] [Film formation] In one embodiment, a film containing a compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution containing a composition containing the compound of the present invention is applied to a surface, and a film is formed after removing the solvent. Wet processes include, but are not limited to, spin coating, slit coating, inkjet printing (spraying), gravure printing, offset printing, and flexographic printing. In the wet process, an appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In one embodiment, a substituent (e.g., an alkyl group) that increases the solubility in organic solvents can be introduced into the compound contained in the composition. In some embodiments, a film containing the compound of the present invention can be formed by a dry process. In some embodiments, the dry process can be a vacuum deposition process, but is not limited thereto. When a vacuum deposition process is used, the compounds constituting the film can be co-deposited from separate deposition sources, or from a single deposition source containing a mixture of compounds. When a single deposition source is used, a mixed powder of compound powders can be used, a compressed compact of the mixed powder can be used, or a mixture of the compounds can be used by heating, melting, and cooling. In some embodiments, co-deposition can be performed under conditions where the deposition rates (weight loss rates) of multiple compounds contained in a single deposition source are the same or nearly the same, thereby forming a film with a composition ratio corresponding to the composition ratio of the multiple compounds contained in the deposition source. By mixing multiple compounds in the same composition ratio as the composition ratio of the film to be formed and using the deposition source as a deposition source, a film with a desired composition ratio can be easily formed. In some embodiments, the temperature at which each of the co-deposited compounds has the same weight loss rate can be identified, and that temperature can be used as the temperature during co-deposition.

[0057] [Examples of use of the compound represented by formula (1)] The compound represented by the general formula (1) is useful as a material for organic light-emitting devices, and is particularly preferably used for organic light-emitting diodes. Organic Light-Emitting Diode: One aspect of the present invention relates to the use of a compound represented by general formula (1) of the present invention as an emitting material in an organic light-emitting device. In some embodiments, the compound represented by general formula (1) of the present invention can be effectively used as an emitting material in the emitting layer of an organic light-emitting device. In some embodiments, the compound represented by general formula (1) includes a delayed fluorescent material (delayed fluorescent material) that emits delayed fluorescence. In some embodiments, the present invention provides a delayed fluorescent material having a structure represented by general formula (1). In some embodiments, the present invention relates to the use of a compound represented by general formula (1) as a delayed fluorescent material. In some embodiments, the compound represented by general formula (1) can be used as a host material and can be used together with one or more emitting materials, which may be fluorescent materials, phosphorescent materials, or TADF materials. In some embodiments, the compound represented by general formula (1) can also be used as a hole transport material. In some embodiments, the compound represented by general formula (1) can be used as an electron transport material. In some embodiments, the present invention relates to a method for producing delayed fluorescence from a compound represented by general formula (1). In some embodiments, an organic light-emitting device containing the compound as an emitting material emits delayed fluorescence and exhibits high light emission efficiency. In some embodiments, the light-emitting layer comprises a compound represented by Formula (1), and the compound represented by Formula (1) is aligned parallel to the substrate. In some embodiments, the substrate is a film-forming surface. In some embodiments, the orientation of the compound represented by Formula (1) relative to the film-forming surface influences or dictates the propagation direction of light emitted by the aligned compound. In some embodiments, aligning the propagation direction of light emitted by the compound represented by Formula (1) improves light extraction efficiency from the light-emitting layer. One aspect of the present invention relates to an organic light-emitting device. In one embodiment, the organic light-emitting device includes an emitting layer. In one embodiment, the emitting layer includes a compound represented by general formula (1) as an emitting material. In one embodiment, the organic light-emitting device is an organic photoluminescence device (organic PL device). In one embodiment, the organic light-emitting device is an organic electroluminescence device (organic EL device). In one embodiment, the compound represented by general formula (1) assists the light emission of other emitting materials included in the emitting layer (as a so-called assist dopant). In one embodiment, the compound represented by general formula (1) included in the emitting layer has its lowest excited singlet energy level, which is between the lowest excited singlet energy level of the host material included in the emitting layer and the lowest excited singlet energy level of the other emitting materials included in the emitting layer. In some embodiments, the organic photoluminescent device includes at least one light-emitting layer. In some embodiments, the organic electroluminescent device includes at least an anode, a cathode, and an organic layer between the anode and the cathode. In some embodiments, the organic layer includes at least an light-emitting layer. In some embodiments, the organic layer includes only an light-emitting layer. In some embodiments, the organic layer includes one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In some embodiments, the hole transport layer may be a hole injection transport layer with hole injection functionality, and the electron transport layer may be an electron injection transport layer with electron injection functionality.

[0058] Emitting layer: In some embodiments, the light-emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons, hi some embodiments, the layer emits light. In some embodiments, only an emitting material is used as the emitting layer. In some embodiments, the emitting layer includes an emitting material and a host material. In some embodiments, the emitting material is one or more compounds represented by general formula (1). In some embodiments, to improve the light emission efficiency of organic electroluminescent devices and organic photoluminescent devices, singlet and triplet excitons generated in the emitting material are confined within the emitting material. In some embodiments, a host material is used in addition to the emitting material in the emitting layer. In some embodiments, the host material is an organic compound. In some embodiments, the organic compound has singlet and triplet excited energies, at least one of which is higher than those of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons generated in the emitting material of the present invention are confined within the molecules of the emitting material of the present invention. In some embodiments, the singlet and triplet excitons are sufficiently confined to improve the light emission efficiency. In some embodiments, the singlet and triplet excitons are not sufficiently confined while still achieving high light emission efficiency. That is, any host material that can achieve high light emission efficiency can be used in the present invention without particular limitations. In some embodiments, light emission occurs in the light-emitting material in the light-emitting layer of the device of the present invention. In some embodiments, the emitted light includes both fluorescence and delayed fluorescence. In some embodiments, the emitted light includes light emitted from the host material. In some embodiments, the emitted light consists of light emitted from the host material. In some embodiments, the emitted light includes light emitted from the compound represented by general formula (1) and light emitted from the host material. In some embodiments, a TADF molecule and a host material are used. In some embodiments, TADF is an assist dopant, and has a lower excited singlet energy than the host material in the light-emitting layer and a higher excited singlet energy than the light-emitting material in the light-emitting layer.

[0059] When the compound represented by general formula (1) is used as an assist dopant, various compounds can be used as the light-emitting material (preferably a fluorescent material). Examples of such light-emitting materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, and derivatives containing metals (Al, Zn). These exemplary skeletons may or may not have a substituent. Furthermore, these exemplary skeletons may be combined with each other. Examples of light-emitting materials that can be used in combination with the assist dopant having the structure represented by general formula (1) are given below.

[0060] [ka] JPEG0007752866000054.jpg223161JPEG0007752866000055.jpg255168

[0061] Furthermore, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 can also be particularly preferably used as light-emitting materials used together with the assist dopant having the structure represented by general formula (1).

[0062] Further preferred light-emitting materials include compounds represented by the following general formula (E1). [ka]

[0063] In general formula (E1), R 1 , R 3 ~R16 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 2 represents an acceptor group, or R 1 and R 2 are bonded to each other to form an acceptor group, or R 2 and R 3 are bonded to each other to form an acceptor group. 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 may be bonded to each other to form a cyclic structure. 1 represents O or NR, and R represents a substituent. X 2 ~X 4 Of these, X 3 and X 4 At least one of the groups is O or NR, and the remaining group may be O or NR or may not be linked. When they are not linked, each 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. 16may be substituted with N.

[0064] Further preferred light-emitting materials include compounds represented by the following general formula (E2). [ka]

[0065] 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 R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 2 , R 2 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 1 may be bonded to each other to form a cyclic structure. 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , C.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.

[0066] Further preferred light-emitting materials include compounds represented by the following general formula (E3). [ka]

[0067] In general 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 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , R 8 and R 9 may be bonded to each other to form a cyclic structure, provided that Z 1 , Z 2 , R 1 and R 2 are bonded to each other to form a ring, R 2 and R 3 are bonded to each other to form a ring, R 4 and R 5 are bonded to each other to form a ring, and R 5 and R 6 at least one of the rings formed by bonding to each other is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole, and R 1~R 9 At least one of Z is a substituted or unsubstituted aryl group or an acceptor group, or 1 and Z 2 At least one of the rings has an aryl group or an acceptor group as a substituent. Among the carbon atoms constituting the benzene ring skeleton constituting the benzofuran ring, the benzothiophene ring, and the indole ring, a substitutable carbon atom may be substituted with a nitrogen atom. 1 , C.R. 2 , C.R. 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 may be substituted with N.

[0068] Further preferred light-emitting materials include compounds represented by the following general formula (E4). [ka]

[0069] In general formula (E4), Z 1 represents a furan ring fused with a substituted or unsubstituted benzene ring, a thiophene ring fused with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring fused with a substituted or unsubstituted benzene ring; Z 2 and Z 3 each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R 1 represents a hydrogen atom, a deuterium atom or a substituent, and R 2 and R 3 Each of Z independently represents a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. 1 and R 1 , R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3may be bonded to each other to form a ring structure, provided that R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one pair of these is bonded to each other to form a ring structure.

[0070] Further preferred light-emitting materials include compounds represented by the following general formula (E5). [ka]

[0071] 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, provided that R 1 , R 2 , Z 1 and Z 2 At least one of R contains a substituted or unsubstituted benzofuran ring, a substituted or unsubstituted benzothiophene ring, or a substituted or unsubstituted indole ring. 1 and Z 1 , Z 1 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and Z 2 , 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.

[0072] Further preferred light-emitting materials include compounds represented by the following general formula (E6). [ka]

[0073] 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 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R15 , 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 six-membered ring, and R 17 and R 18 When they are bonded to each other to form a single bond, R 1 ~R 6 At least one of R is a substituted or unsubstituted aryl group, or R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 are bonded to each other to form an aromatic ring or a heteroaromatic ring.

[0074] Further preferred light-emitting materials include compounds represented by the following general formula (E7). [ka]

[0075] 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 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 , R219 and R 220 , R 220 and R 221 One or two of the groups are bonded to each other 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 or 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).

[0076] Furthermore, compounds represented by 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 incorporated herein by reference as part of this specification.

[0077] In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 0.1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 1% by weight or more. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 50% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 20% by weight or less. In some embodiments, when a host material is used, the amount of the compound of the present invention as the light-emitting material in the light-emitting layer is 10% by weight or less. In some embodiments, the host material of the light-emitting layer is an organic compound that has hole-transporting and electron-transporting functions. In some embodiments, the host material of the light-emitting layer is an organic compound that prevents the wavelength of emitted light from increasing. In some embodiments, the host material of the light-emitting layer is an organic compound that has a high glass transition temperature.

[0078] In some embodiments, the host material is selected from the group consisting of: [ka] In one embodiment, the light-emitting layer contains two or more TADF molecules with different structures. For example, the light-emitting layer may contain three materials, the host material, the first TADF molecule, and the second TADF molecule, whose excited singlet energy levels are highest in this order. In this case, the first TADF molecule and the second TADF molecule both have a difference ΔE between their lowest excited singlet energy levels and the lowest excited triplet energy level at 77 K. STis preferably 0.3 eV or less, more preferably 0.25 eV or less, more preferably 0.2 eV or less, more preferably 0.15 eV or less, even more preferably 0.1 eV or less, even more preferably 0.07 eV or less, even more preferably 0.05 eV or less, even more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less. The concentration of the first TADF molecules in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. The concentration of the host material in the light-emitting layer is preferably greater than the concentration of the second TADF molecules. The concentration of the first TADF molecules in the light-emitting layer may be greater than, less than, or the same as the concentration of the host material. In some embodiments, the composition in the light-emitting layer may be 10 to 70 wt % of the host material, 10 to 80 wt % of the first TADF molecules, and 0.1 to 30 wt % of the second TADF molecules. In one embodiment, the composition of the light-emitting layer may be 20 to 45 wt % of the host material, 50 to 75 wt % of the first TADF molecules, and 5 to 20 wt % of the second TADF molecules. In one embodiment, the photo-excited luminescence quantum yield φPL1(A) of a co-deposited film of the first TADF molecules and the host material (where the concentration of the first TADF molecules in the co-deposited film is A wt %) and the photo-excited luminescence quantum yield φPL2(A) of a co-deposited film of the second TADF molecules and the host material (where the concentration of the second TADF molecules in the co-deposited film is A wt %) satisfy the relationship φPL1(A) > φPL2(A). In one embodiment, the photo-excited luminescence quantum yield φPL2(B) of a co-deposited film of the second TADF molecules and the host material (where the concentration of the second TADF molecules in the co-deposited film is B wt %) and the photo-excited luminescence quantum yield φPL2(100) of a film of the second TADF molecules alone satisfy the relationship φPL2(B) > φPL2(100). In some embodiments, the light-emitting layer may contain three structurally different TADF molecules, and the compound of the present invention may be any of the TADF compounds contained in the light-emitting layer. In some embodiments, the light-emitting layer can be composed of a material selected from the group consisting of a host material, an assist dopant, and a light-emitting material. In some embodiments, the light-emitting layer does not contain a metal element. In some embodiments, the light-emitting layer can be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. Alternatively, the light-emitting layer can be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the light-emitting layer can be composed of a material consisting only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. When the light-emitting layer contains a TADF material other than the compound of the present invention, the TADF material may be a known delayed fluorescent material. Preferred delayed fluorescent materials include those described in paragraphs 0008 to 0048 and 0095 to 0133 of WO2013 / 154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013 / 011955, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013 / 081088, and ~0071 and 0118~0133, paragraphs 0009~0046 and 0093~0134 of JP 2013-256490 A, paragraphs 0008~0020 and 0038~0040 of JP 2013-116975 A, paragraphs 0007~0032 and 0079~0084 of WO2013 / 133359 A, paragraph 0 of WO2013 / 161437 A 008 to 0054 and 0101 to 0121, paragraphs 0007 to 0041 and 0060 to 0069 of JP 2014-9352 A, paragraphs 0008 to 0048 and 0067 to 0076 of JP 2014-9224 A, paragraphs 0013 to 0025 of JP 2017-119663 A, paragraphs 0013 to 0026 of JP 2017-119664 A, Compounds encompassed by the general formulas described in paragraphs 0012 to 0025 of JP 017-222623 A, paragraphs 0010 to 0050 of JP 2017-226838 A, paragraphs 0012 to 0043 of JP 2018-100411 A, and paragraphs 0016 to 0044 of WO 2018 / 047853 A, particularly exemplary compounds, that are capable of emitting delayed fluorescence are included.Further, here, the following patent documents are disclosed: JP 2013-253121 A, WO2013 / 133359 A, WO2014 / 034535 A, WO2014 / 115743 A, WO2014 / 122895 A, WO2014 / 126200 A, WO2014 / 136758 A, WO2014 / 133121 A, WO20 14 / 136860, WO2014 / 196585, WO2014 / 189122, WO2014 / 168101, WO2015 / 008 580 publication, WO2014 / 203840 publication, WO2015 / 002213 publication, WO2015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP2015-129240A, WO2015 / 129714, WO2015 / 129715, WO2015 / 13350 Preferably, the luminescent materials capable of emitting delayed fluorescence are those described in WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541. The above publications described in this paragraph are incorporated herein by reference.

[0079] Each component of the organic electroluminescence element and each layer other than the light-emitting layer will be described below.

[0080] Base material: In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate, and the substrate is not particularly limited and may be any material commonly used in organic electroluminescent devices, such as glass, transparent plastic, quartz, and silicon.

[0081] anode: In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, a conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or greater). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO, and ZnO. In some embodiments, an amorphous material capable of forming a transparent conductive film, such as In2O3-ZnO, is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is formed by evaporation or sputtering. In some embodiments, the film is patterned by a photolithography method. In some embodiments, if the pattern does not need to be highly precise (e.g., greater than about 100 μm), the pattern may be formed using a mask with a shape suitable for evaporation or sputtering of the electrode material. In some embodiments, when a coating material, such as an organic conductive compound, can be applied, a wet film formation method, such as a printing method or a coating method, is used. In some embodiments, the anode has a transmittance of greater than 10% when emitted light passes through it, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the anode has a thickness of 10 to 1,000 nm. In some embodiments, the anode has a thickness of 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[0082] cathode: In some embodiments, the cathode is made of an electrode material such as a metal with a low work function (4 eV or less) (referred to as an electron-injecting metal), alloy, conductive compound, or a combination thereof. In some embodiments, the electrode material is selected from sodium, sodium-potassium alloy, magnesium, lithium, magnesium-copper mixture, magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, indium, lithium-aluminum mixture, and rare earth elements. In some embodiments, a mixture of an electron-injecting metal and a second metal, which is a stable metal having a higher work function than the electron-injecting metal, is used. In some embodiments, the mixture is selected from magnesium-silver mixture, magnesium-aluminum mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al2O3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture improves electron-injecting properties and oxidation resistance. In some embodiments, the cathode is fabricated by forming the electrode material as a thin film by evaporation or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the cathode has a thickness of 10 nm to 5 μm. In some embodiments, the cathode has a thickness of 50 to 200 nm. In some embodiments, one of the anode and cathode of the organic electroluminescent device is transparent or semitransparent to transmit emitted light. In some embodiments, a transparent or semitransparent electroluminescent device improves light radiance. In some embodiments, the cathode is formed from a conductive, transparent material as described above for the anode, thereby forming a transparent or semi-transparent cathode. In some embodiments, a device includes an anode and a cathode, both of which are transparent or semi-transparent.

[0083] Injection layer: An injection layer is a layer between an electrode and an organic layer. In some embodiments, the injection layer reduces driving voltage and enhances light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be disposed between the anode and the emissive layer or the hole transport layer, and between the cathode and the emissive layer or the electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present. Preferred examples of compounds that can be used as hole injection materials are listed below.

[0084] [ka]

[0085] Next, preferred examples of compounds that can be used as the electron injection material will be listed. [ka]

[0086] Barrier layer: A blocking layer is a layer that can prevent charges (electrons or holes) and / or excitons present in the light-emitting layer from diffusing outside the light-emitting layer. In some embodiments, an electron blocking layer is present between the light-emitting layer and the hole transport layer and prevents electrons from passing through the light-emitting layer to the hole transport layer. In some embodiments, a hole blocking layer is present between the light-emitting layer and the electron transport layer and prevents holes from passing through the light-emitting layer to the electron transport layer. In some embodiments, a blocking layer prevents excitons from diffusing outside the light-emitting layer. In some embodiments, the electron blocking layer and the hole blocking layer constitute an exciton blocking layer. As used herein, the terms "electron blocking layer" or "exciton blocking layer" include layers that have both the functionality of an electron blocking layer and an exciton blocking layer.

[0087] Hole blocking layer: The hole blocking layer functions as an electron transport layer. In some embodiments, the hole blocking layer prevents holes from reaching the electron transport layer during electron transport. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the hole blocking layer can be the same materials as those described above for the electron transport layer. Preferred examples of compounds that can be used in the hole blocking layer are listed below.

[0088] [ka]

[0089] Electron barrier layer: The electron blocking layer transports holes. In some embodiments, during hole transport, the electron blocking layer prevents electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The materials used for the electron blocking layer can be the same materials as those described above for the hole transport layer. Specific examples of preferred compounds that can be used as electron blocking materials are listed below.

[0090] [ka]

[0091] Exciton blocking layer: The exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the emissive layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer enables effective confinement of excitons in the emissive layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton blocking layer is adjacent to the emissive layer on either the anode side or the cathode side, and on both sides. In some embodiments, when the exciton blocking layer is present on the anode side, it may be present between the hole transport layer and the emissive layer and adjacent to the emissive layer. In some embodiments, when the exciton blocking layer is present on the cathode side, it may be present between the emissive layer and the cathode and adjacent to the emissive layer. In some embodiments, a hole injection layer, an electron blocking layer, or a similar layer is present between the anode and the exciton blocking layer adjacent to the emissive layer on the anode side. In some embodiments, a hole injection layer, an electron blocking layer, a hole blocking layer, or a similar layer is present between the cathode and the exciton blocking layer adjacent to the emissive layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and excited triplet energy, respectively, of the light-emitting material.

[0092] Hole transport layer: The hole transport layer comprises a hole transport material. In some embodiments, the hole transport layer is a single layer. In some embodiments, the hole transport layer has multiple layers. In some embodiments, the hole transport material has one of hole injection or transport properties and electron blocking properties. In some embodiments, the hole transport material is an organic material. In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are listed below.

[0093] [ka]

[0094] 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.

[0095] [ka]

[0096] 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.

[0097] [ka]

[0098] 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.

[0099] device: In some embodiments, the light-emitting layer is incorporated into a device, including, but not limited to, an OLED bulb, an OLED lamp, a television display, a computer monitor, a mobile phone, and a tablet. In some embodiments, the electronic device comprises an OLED having an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the compositions can be useful for facilitating charge or energy transfer within devices and / or as hole transport materials, such as organic light-emitting diodes (OLEDs), organic integrated circuits (OICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light-emitting fuel cells (LECs), or organic laser diodes (O-lasers).

[0100] Bulb or Lamp: In some embodiments, the electronic device comprises an OLED comprising an anode, a cathode, and at least one organic layer comprising an emissive layer between the anode and the cathode. In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device includes an array including a combination of OLEDs. In some embodiments, the combination of OLEDs is a three-color combination (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors that are not red, green, or blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a two-color, four-color, or more-color combination. In some embodiments, the device comprises: a circuit board having a first side with a mounting surface and an opposite second side, the circuit board defining at least one opening; at least one OLED on the mounting surface, the at least one OLED having a light-emitting configuration including an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode; a housing for the circuit board; and at least one connector disposed on an end of the housing, the housing and the connector defining a package suitable for attachment to a lighting fixture. In some embodiments, the OLED light comprises multiple OLEDs mounted on a circuit board such that light is emitted in multiple directions. In some embodiments, some of the light emitted in a first direction is polarized and emitted in a second direction. In some embodiments, a reflector is used to polarize the light emitted in the first direction.

[0101] Display or Screen: In some embodiments, the light-emitting layer of the present invention can be used in a screen or display. In some embodiments, the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD). In some embodiments, the substrate is a photoplate structure useful for two-sided etching to provide pixels with unique aspect ratios. The screen (also called a mask) is used in the manufacturing process of OLED displays. The corresponding artwork pattern design allows for the placement of very steep, narrow tie bars between pixels in the vertical direction and large, wide, beveled openings in the horizontal direction. This allows for the fine patterning of pixels required for high-resolution displays while optimizing chemical vapor deposition onto the TFT backplane. Internal pixel patterning allows for the construction of three-dimensional pixel openings with various aspect ratios in the horizontal and vertical directions. Furthermore, the use of imaged "stripes" or halftone circles within the pixel area protects etching in specific regions until these specific patterns are undercut and removed from the substrate. At that point, all pixel areas are subjected to similar etch rates, but the depth varies depending on the halftone pattern. Varying the size and spacing of the halftone patterns allows for etching with varying degrees of protection within the pixel, enabling the deep, localized etching required to create steep vertical bevels. The preferred material for the deposition mask is Invar, a metal alloy that is cold-rolled into long, thin sheets at steel mills. Invar cannot be electrodeposited onto the spin mandrel as a nickel mask. A suitable, low-cost method for forming open areas in the deposition mask is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography). In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In further embodiments, the screen or display pattern is fabricated using plasma etching.

[0102] Device manufacturing method: OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarizing film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel. OLED displays are generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels. Typically, each cell panel on the mother panel is formed by forming a thin film transistor (TFT) having an active layer and source / drain electrodes on a base substrate, applying a planarizing film to the TFT, sequentially forming a pixel electrode, an emissive layer, a counter electrode, and an encapsulation layer, and then cutting the mother panel.

[0103] In another aspect of the present invention, there is provided a method for manufacturing an organic light emitting diode (OLED) display, the method comprising: forming a barrier layer on a base substrate of the mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer over each of the display units of the cell panel; and applying an organic film to the interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example, made of SiNx, and the edges of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film helps the mother panel to be softly cut into individual cell panels. In some embodiments, the thin film transistor (TFT) layer includes a light-emitting layer, a gate electrode, and source / drain electrodes. Each of the plurality of display units may include a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light-emitting unit formed on the planarization film, and the organic film applied to the interface is formed of the same material as the planarization film and is formed simultaneously with the planarization film. In some embodiments, the light-emitting unit is connected to the TFT layer by a passivation layer, the planarization film therebetween, and an encapsulation layer that covers and protects the light-emitting unit. In some embodiments of the manufacturing method, the organic film is not connected to either the display unit or the encapsulation layer.

[0104] Each of the organic film and the planarization film may comprise one of polyimide and acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. The method may further include attaching a carrier substrate formed of a glass material to one surface of the base substrate formed of polyimide before forming the barrier layer on the other surface of the base substrate, and separating the carrier substrate from the base substrate before cutting along the interface. In some embodiments, the OLED display is a flexible display. In some embodiments, the passivation layer is an organic film disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is an organic film formed on the passivation layer. In some embodiments, the planarization film is formed of polyimide or acrylic, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of an OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer, such that a portion of the organic film directly contacts the base substrate and a remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

[0105] In some embodiments, the light-emitting layer comprises a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode, hi some embodiments, the pixel electrode is coupled to a source / drain electrode of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, a suitable voltage is formed between the pixel electrode and the counter electrode, which causes the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image-forming unit having a TFT layer and a light-emitting unit is referred to as a display unit. In some embodiments, the encapsulation layer that covers the display units and prevents penetration of external moisture may be formed into a thin-film encapsulation structure in which organic films and inorganic films are alternately stacked. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which multiple thin films are stacked. In some embodiments, the organic film applied to the interface portion is disposed at an interval with each of the multiple display units. In some embodiments, the organic film is formed in such a manner that a portion of the organic film directly contacts the base substrate and the remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer.

[0106] In one embodiment, the OLED display is flexible and uses a flexible base substrate formed of polyimide, hi some embodiments, the base substrate is formed on a carrier substrate formed of a glass material, and the carrier substrate is then separated. In some embodiments, a barrier layer is formed on the surface of the base substrate opposite the carrier substrate. In one embodiment, the barrier layer is patterned according to the size of each cell panel. For example, while the base substrate is formed on all surfaces of the mother panel, the barrier layer is formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the grooves.

[0107] In some embodiments, the manufacturing method further includes a step of cutting along the interface, in which a groove is formed in the barrier layer and at least a portion of the organic film is formed in the groove, so that the groove does not penetrate the base substrate. In some embodiments, the TFT layer of each cell panel is formed, and a passivation layer (an inorganic film) and a planarization film (an organic film) are disposed on and cover the TFT layer. At the same time as the planarization film (e.g., polyimide or acrylic) is formed, the grooves at the interface are covered with an organic film (e.g., polyimide or acrylic). This prevents cracks from occurring when each cell panel is cut along the grooves at the interface by allowing the organic film to absorb any impacts that may occur. That is, if all barrier layers were completely exposed without the organic film, the impacts would be transmitted to the barrier layers when each cell panel was cut along the grooves at the interface, thereby increasing the risk of cracks. However, in one embodiment, the grooves at the interface between the barrier layers are covered with an organic film to absorb any impacts that would otherwise be transmitted to the barrier layers, allowing each cell panel to be cut softly and preventing cracks from occurring in the barrier layers. In one embodiment, the organic film and the planarizing film covering the groove of the interface portion are spaced apart from each other. For example, if the organic film and the planarizing film are connected to each other as one layer, external moisture may penetrate into the display unit through the planarizing film and the remaining portion of the organic film, so the organic film and the planarizing film are spaced apart from each other so that the organic film is spaced apart from the display unit.

[0108] In some embodiments, the display unit is formed by forming a light-emitting unit, and an encapsulation layer is disposed on the display unit to cover the display unit. Thus, after the mother panel is completely manufactured, the carrier substrate carrying the base substrate is separated from the base substrate. In some embodiments, when a laser beam is irradiated onto the carrier substrate, the carrier substrate is separated from the base substrate due to the difference in thermal expansion coefficient between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into individual cell panels. In some embodiments, the mother panel is cut along the interface between the cell panels using a cutter. In some embodiments, the grooves at the interface along which the mother panel is cut are covered with an organic film, which absorbs shock during cutting. In some embodiments, this can prevent cracks from occurring in the barrier layer during cutting. In some embodiments, the method reduces product rejection rates and stabilizes product quality. Another embodiment is an OLED display having a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic film applied to the edges of the barrier layer. [Example]

[0109] The following synthesis examples and working examples will further illustrate the features of the present invention. The materials, processing details, processing procedures, etc. shown below can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. The emission characteristics were evaluated using a source meter (Keithley: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter (Newport: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334). In the following synthesis examples, compounds within the general formula (1) were synthesized.

[0110] (Synthesis Example 1) Synthesis of Compound 3 [ka]

[0111] Compound A Under a nitrogen stream, a 1M aqueous potassium carbonate solution (50 mL) and tetrakistriphenylphosphinepalladium(0) (0.93 g, 0.81 mmol) were added to a solution of 1,4-dibromotetrafluorobenzene (5.01 g, 16.2 mmol) and 4-cyanophenylboronic acid (5.25 g, 35.7 mmol) in tetrahydrofuran (200 mL) and stirred at 80°C for 15 hours. The reaction solution was returned to room temperature, extracted with chloroform, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane:toluene = 1:4) to obtain 2.00 g (5.68 mmol, 35% yield) of compound A as a white solid. 1 H-NMR (400 MHz, CDCl3): δ 7.83 (d, J= 8.0 Hz, 4H), 7.65 (d, J = 8.0 Hz, 4H). ASAP MS Spectral Analysis: C 20 H8F4N2: Calculated 352.06, Observed 353.22 [M+H + ]

[0112] Compound B Under a nitrogen stream, potassium carbonate (0.60 g, 4.37 mmol) was added to a solution of compound A (0.77 g, 2.18 mmol) and carbazole (0.73 g, 4.37 mmol) in N,N-dimethylformamide (150 mL), and the mixture was stirred at 100°C for 15 hours. The reaction mixture was returned to room temperature, water and methanol were added, and the mixture was filtered. The residue was purified by silica gel column chromatography (hexane:chloroform = 1:9) to obtain 0.95 g (1.47 mmol, 67% yield) of compound B as a yellow solid. 1H-NMR (400 MHz, CDCl3): δ 8.06 (d, J = 7.8 Hz, 4H), 7.39 (t, J = 7.8 Hz, 4H), 7.31-7.28 (m, 8H), 7.23 (d, J = 7.2 Hz, 4H), 7.16 (d, J = 7.8 Hz, 4H). ASAP MS Spectral Analysis: C 44 H 24 F2N4: Calculated 646.20, Observed 647.48 [M+H + ]

[0113] compound 3 Under a nitrogen stream, potassium carbonate (0.37 g, 2.71 mmol) was added to a solution of compound B (0.70 g, 1.08 mmol) and 5H-benzofuro[3,2-C]carbazole (0.70 g, 2.71 mmol) in N,N-dimethylformamide (140 mL) and stirred at 150 °C for 15 hours. The reaction mixture was returned to room temperature, water and methanol were added, and the mixture was filtered. The residue was purified by silica gel column chromatography (hexane:chloroform:ethyl acetate=1:1:0.1) to obtain 0.56 g (0.50 mmol, 46% yield) of compound 3 as a pale yellow solid. 1 H-NMR (400 MHz, CDCl3): δ 8.06 (d, J = 7.2 Hz, 2H), 7.87 (d, J = 7.2 Hz, 2H), 7.61-7.56 (m, 8H), 7.39 (t, J = 7.8 Hz, 2H), 7.33 (t, J = 7.2 Hz, 2H), 7.22-6.89 (m, 20H), 6.80-6.77 (m, 4H) 6.67-6.62 (m, 4H). ASAP MS Spectral Analysis: C 80 H 44 N6O2: Calculated 1120.35, Observed 1121.84 [M+H + ]

[0114] (Synthesis Example 2) Synthesis of Compound 19281 [ka]

[0115] Compound C To a solution of 1,5-dibromo-2,3,4-trifluorobenzene (5.80 g, 20.0 mmol) and bis(pinacolato)diboron (12.7 g, 50.0 mmol) in 1,4-dioxane (100 mL), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.88 g, 1.20 mmol) and potassium acetate (9.82 g, 100 mmol) were added under a nitrogen atmosphere and stirred at 110 °C. After 15 h, the reaction mixture was allowed to warm to room temperature, and the solvent was evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate = 4:1) to give compound C (7.36 g, 19.2 mmol, 96% yield) as a brown solid. ASAP Mass Spectral Analysis: Theoretical value: 384.19, observed value: 385.21.

[0116] Compound D A solution of compound C (3.84 g, 10.0 mmol) and 3-bromo-2-pyridinecarbonitrile (4.21 g, 23.0 mmol) in toluene / water (90 mL / 10 mL) was added with 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (82.0 mg, 0.20 mmol), tris(dibenzylideneacetone)dipalladium(0) (92.0 mg, 0.10 mmol), and tripotassium phosphate (4.25 g, 20.0 mmol) under a nitrogen atmosphere and stirred at room temperature for 15 hours. The mixture was then returned to room temperature, washed with saturated aqueous ammonium chloride and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The resulting mixture was purified by silica gel column chromatography (hexane:ethyl acetate = 2:1) to give compound D (0.51 g, 1.50 mmol, 15% yield) as a white solid. 1H-NMR (400 MHz, CDCl3): δ 8.81 (dd, J = 4.8, 1.5 Hz, 2H), 7.96 (dd, J = 8.0, 1.3 Hz, 2H), 7.68 (d, J = 8.0 Hz, 1H), 7.67 (d, J= 8.0 Hz, 1H), 7.38 (td, J = 7.1, 2.4 Hz, 1H). ASAP mass spectrum analysis: Calculated 336.06, observed 338.18

[0117] Compound 19281 and Compound E Under a nitrogen stream, 2.26 g (8.80 mmol) of 5H-benzofuro[3,2-c]carbazole and 1.66 g (12.0 mmol) of potassium carbonate were added to N,N-dimethylformamide (25 mL) and stirred at room temperature for 1 hour. 1.35 g (4.00 mmol) of compound D was added to the reaction mixture, and the mixture was stirred at room temperature for 15 hours. After that, the mixture was heated to 60 °C and stirred for 24 hours. The reaction solution was returned to room temperature, water was added, and the precipitate was filtered off. The residue was washed with methanol and dried under vacuum. The residue was purified by silica gel column chromatography (toluene:ethyl acetate = 85:15) to give compound 19281 (1.32 g, 1.26 mmol, yield 32%) and compound E (0.89 g, 1.10 mmol, yield 27%) as a pale yellow solid. Compound 19281: 1 H NMR (400 MHz, CDCl3,): δ 8.49 (s, 1H), 8.39-8.29 (m, 2H), 8.07-7.94 (m, 4H), 7.74-7.15 (m, 18H), 7.01-6.98 (m, 5H), 6.89-6.79 (m, 5H), 6.69-6.62 (m, 2H). ASAP MS spectrum analysis: Calculated 1047.30, Observed 1048.53 Compound E: 1H NMR (400 MHz, CDCl3): δ 8.45 (d, J = 7.7 Hz, 2H), 8.41-8.04 (m, 2H), 8.05 (s, 1H), 7.98 (t, J = 8.1 Hz, 4H), 7.70 (d, J = 8.1 Hz, 2H), 7.54-7.29 (m, 17H), 7.03-6.98 (m, 2H). ASAP MS spectrum analysis: Calculated 810.22, Observed 811.39

[0118] (Synthesis Example 3) Synthesis of Compound 13773 [ka]

[0119] Compound 13773 Under a nitrogen stream, 9H-carbazole (0.33 g, 1.95 mmol) and potassium carbonate (0.31 g, 2.25 mmol) were added to N,N-dimethylformamide (25 mL) and stirred at room temperature for 1 hour. Compound E (1.22 g, 1.50 mmol) was added to the reaction mixture and stirred at 100°C for 20 hours. The reaction solution was returned to room temperature, water was added, and the precipitate was filtered off. The filter cake was washed with methanol and dried under vacuum. The residue was purified by silica gel column chromatography (toluene:ethyl acetate = 98:2) to obtain compound 13773 (1.09 g, 1.14 mmol, 76% yield) as a pale yellow solid. 1 H NMR (400 MHz, CDCl3): δ 8.45 (s, 1H), 8.33 (s, 2H), 8.04-7.97 (m, 4H), 7.73-7.72 (m, 1H), 7.57-7.51 (m, 5H), 7.39 (d, J = 6.4 Hz, 4H), 7.17-7.13 (m, 3H), 6.99 (t, 5H), 6.82-6.77 (m, 2H), 6.76-6.65 (td, 4H), 6.60 (t, J = 7.2 Hz, 1H). ASAP MS spectrum analysis: Calculated 957.29, Observed 958.46

[0120] According to the same procedures as in Synthesis Examples 1 to 3, the following Compound 23430, Compound 15609, Compound 19740, Compound 921, Reference Compound 1 and Reference Compound 2 were also synthesized. [ka]

[0121] (Example 1) Preparation and evaluation of thin films Vacuum deposition method on a quartz substrate at a vacuum level of 1 x 10 -3 Compound 3 was evaporated under conditions of less than 10 Pa to form a neat thin film of Compound 3 with a thickness of 100 nm. Separately, a vacuum of 1×10 was deposited on a quartz substrate by vacuum deposition. -3 Compound 3 and PYD2Cz were evaporated from different evaporation sources under conditions of less than Pa, and a doped thin film with a concentration of Compound 3 of 20 wt % was formed to a thickness of 100 nm. Using Compound 13773 and Compound 19281 instead of Compound 3, neat and doped thin films were prepared in the same manner. The lowest excited singlet energy and the lowest excited triplet energy were measured using each neat thin film, and the difference ΔE ST was calculated. In addition, the maximum emission wavelength (λmax) and photoluminescence quantum yield (PLQY) were measured when each doped thin film was irradiated with 300 nm excitation light. The results are shown in Table 3. The maximum emission wavelengths of Reference Compound 1 and Reference Compound 2 were also measured in the same manner, and were found to be 458 nm and 469 nm. Compound 3, Compound 13773, Compound 19281, Reference Compound 1, and Reference Compound 2 were all confirmed to have a good deep blue emission color. [Table 3]

[0122] Doped thin films were formed according to the above method using the following comparative compounds 1 to 4. For comparative compounds 1 to 3, DPEPO was used as the host material. The lifetime of delayed fluorescence was measured using the doped thin films prepared, including those of compound 3, compound 13773, and compound 19281. The results are shown in Table 4. [ka]

[0123] [Table 4]

[0124] Compound 3, compound 13773, and compound 19281, which are represented by general formula (1), had a shorter delayed fluorescence lifetime than comparative compounds 1 to 3. Comparative compound 4 had a delayed fluorescence lifetime at the same level as compound 13773, but had a low photoluminescence quantum yield (PLQY) of 26%, and did not exhibit the excellent luminescence properties of compound 3, compound 13773, and compound 19281. Furthermore, the photoluminescence quantum yields (PLQY) of compound 3, compound 13773, and compound 19281 were higher than those of comparative compound 1 and comparative compound 2, confirming that they had excellent luminescence properties.

[0125] Example 2: Fabrication of an organic electroluminescence device Each thin film was deposited by vacuum deposition on a glass substrate with an anode made of indium tin oxide (ITO) with a thickness of 50 nm, at a vacuum of 5.0 × 10 -5The layers were laminated using a Pa process. First, HAT-CN was formed to a thickness of 10 nm on ITO, NPD was formed to a thickness of 35 nm on top of that, and PTCz was formed to a thickness of 10 nm on top of that. Next, PYD2Cz and compound 3 were co-evaporated from different evaporation sources to form a 40 nm thick layer, which served as the light-emitting layer. The concentration of compound 3 in the light-emitting layer was 30 wt%. Next, ET1 was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-evaporated from different evaporation sources to form a 20 nm thick layer. The concentrations of Liq and SF3-TRZ in this layer were 30 wt% and 70 wt%, respectively. Liq was then formed to a thickness of 2 nm, and then aluminum (Al) was evaporated to a thickness of 100 nm to form a cathode, completing the organic electroluminescence device. [ka] [Industrial Applicability]

[0126] The compound represented by general formula (1) has good light-emitting performance. Therefore, by using the compound represented by general formula (1), an excellent organic light-emitting device can be provided. Therefore, the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1): 【Chemical 1】 In the general formula (1), A represents a cyanopyridyl group, and a hydrogen atom of the cyanopyridyl group may be substituted with a deuterium atom. ２ represents an acceptor group, and the acceptor group is a substituted or unsubstituted heteroaryl group containing a nitrogen atom as a ring skeleton-constituting atom, or a cyano group. １ , R ３ , R ４ , R ５ At least two of R each independently represent a substituted or unsubstituted benzofuro-fused carbazol-9-yl group. １ ~R ５ each independently represents a hydrogen atom, a deuterium atom, an unsubstituted aryl group, or a donor group, and the donor group is a substituted or unsubstituted diarylamino group (however, the two aryl groups constituting the diarylamino group may be bonded to each other, and the substituted or unsubstituted diarylamino group does not include a substituted or unsubstituted benzofuro-fused carbazol-9-yl group and a substituted or unsubstituted benzothieno-fused carbazol-9-yl group).

2. The compound according to claim 1, wherein the maximum emission wavelength is in the range of 420 nm to 480 nm.

3. 3. The compound of claim 1 or 2, which has a symmetrical structure.

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

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

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

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

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

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

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

11. The organic light-emitting device of claim 9 , wherein the device has a layer comprising the compound, the layer also comprising a light-emitting material having a structure different from that of the compound.

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

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

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

15. The organic light-emitting device according to any one of claims 8 to 14, which emits delayed fluorescence.

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