Compound, light-emitting material and light-emitting element

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

[0002] Research is actively being conducted to improve the luminescence efficiency of light-emitting devices such as organic electroluminescent devices (OLEDs). In particular, various methods are being employed to improve luminescence efficiency by newly developing and combining electron transport materials, hole transport materials, and light-emitting materials that constitute organic electroluminescent devices. Among these, there is also research on organic electroluminescent devices that utilize delayed fluorescence materials.

[0003] Delayed fluorescence materials are materials that, in their excited state, emit fluorescence when they return from the excited singlet state to the ground state after undergoing a reverse intersystem crossover from the excited triplet state to the excited singlet state. This fluorescence is called delayed fluorescence because it is observed later than fluorescence directly generated from the excited singlet state (normal fluorescence) from the ground state. For example, when a luminescent compound is excited by carrier injection, the probability of generating the excited singlet state and the excited triplet state is statistically 25%:75%, so there is a limit to improving the luminescence efficiency if only fluorescence from the directly generated excited singlet state is used. On the other hand, with delayed fluorescence materials, not only the excited singlet state but also the excited triplet state can be used for fluorescence emission via the reverse intersystem crossover pathway described above, resulting in higher luminescence efficiency compared to normal fluorescence materials.

[0004] Since this principle was revealed, various studies have led to the discovery of various delayed fluorescence materials. Among them are, for example, the following compounds in which benzene is substituted with two cyanophenyl groups and four substituted or unsubstituted carbazole-9-yl groups (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 [Overview of the project] [Problems that the invention aims to solve]

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

[0009] Under these circumstances, the inventors conducted extensive research with the aim of providing compounds that are more useful as light-emitting materials for light-emitting devices. Furthermore, they diligently pursued studies with the aim of deriving and generalizing general formulas for compounds that are more useful as light-emitting materials. [Means for solving the problem]

[0010] As a result of diligent research to achieve the above objectives, the inventors have found that compounds having a structure that satisfies specific conditions are useful as luminescent materials. The present invention is proposed based on these findings and specifically has the following configuration.

[0011] [1] A compound represented by the following general formula (1). [Chemical formula] [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 them represents an acceptor group. R 2 and R 3 the other of R 1 , R 4 , R 5 at least one of them each independently represents a substituted or unsubstituted benzofuro-fused carbazol-9-yl group or a substituted or unsubstituted benzothieno-fused carbazol-9-yl group. The remaining R 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, and a substituted or unsubstituted benzothieno-fused carbazol-9-yl group).] [2] The compound according to [1], wherein the maximum emission wavelength is in the range of 420 nm to 575 nm. [3] The compound according to [1] or [2], wherein R 2 is an acceptor group. [4] The compound according to [1] or [2], wherein R 3 is an acceptor group. [5] The compound according to any one of [1] to [4], wherein the acceptor group is a group having 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 constituent atom or a cyano group. [7] R 1 ~R 5The compound according to any one of [1] to [6], wherein at least two of are independently substituted or unsubstituted benzoflo-fused carbazole-9-yl groups, or substituted or unsubstituted benzothieno-fused carbazole-9-yl groups. [8] R 2 and R 5 A compound according to any one of [1] to [7], wherein each of the following is an independent 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] A compound having a symmetrical structure, as described in any one of [1] to [9].

[11] A luminescent material comprising any one of the compounds described in [1] to

[10] .

[12] A delayed phosphor comprising any one of the compounds described in [1] to

[10] .

[13] A membrane containing one of the compounds described in [1] to

[10] .

[14] An organic semiconductor device containing one of the compounds described in any one of [1] to

[10] .

[15] An organic light-emitting element comprising one of the compounds described in any one of [1] to

[10] .

[16] The organic light-emitting element according to

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

[17] The organic light-emitting element according to

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

[18] The organic light-emitting element according to

[16] , wherein the element has a layer containing the compound, and the light-emitting material also includes a layer having a structure different from that of the compound.

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

[16] to

[18] , wherein the material contained in the element has the greatest amount of light emitted from the compound.

[20] The organic light-emitting device 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] An organic electroluminescent element, the organic light-emitting element described in any one of

[15] to

[20] .

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

[15] to

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

[0012] Compounds represented by general formula (1) exhibit excellent luminescence properties. General formula (1) includes luminescent materials that emit deep blue light. Furthermore, general formula (1) includes luminescent materials with a short delayed fluorescence lifetime. Excellent organic light-emitting devices can be provided by using compounds represented by general formula (1). [Modes for carrying out the invention]

[0013] The contents of the present invention will be described in detail below. The description of the constituent elements described below may be based on representative embodiments and specific examples of the present invention, but the present invention is not limited to such embodiments and specific examples. In this specification, numerical ranges represented by "~" mean a range that includes the numbers written before and after "~" as the lower limit and upper limit. Also, some or all of the hydrogen atoms present in the molecule of the compound used in the present invention are deuterium atoms ( 2 It can be substituted with H (deuterium D). In the chemical structural formulas herein, hydrogen atoms are represented as H or omitted. For example, when the representation of an atom bonded to a carbon atom in the ring skeleton of a benzene ring is omitted, it is assumed that H is bonded to the carbon atom in the ring skeleton where the representation is omitted. In the chemical structural formulas herein, deuterium atoms are represented as D.

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

[0015] In general formula (1), A represents a cyanopyridyl group which may be substituted with a 2-cyanophenyl group, a 4-cyanophenyl group, or 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 they may not be 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 bond position of the cyano group of the cyanopyridyl group that A can take may be any of the 2-4 positions of the pyridine ring. In one preferred embodiment of the present invention, the cyano group is at position 2 of the pyridine ring. In one embodiment of the present invention, the cyano group is at position 3 of the pyridine ring. In one embodiment of the present invention, the cyano group is at position 4 of the pyridine ring. Furthermore, the bond of the cyanopyridyl group may be any of the 2-6 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, phenyl, and naphthyl groups. Some or all of the phenyl groups referred to here may be substituted with deuterium atoms. Some or all of the naphthyl groups referred to here 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 one embodiment of the present invention, the cyanopyridyl group is substituted with at least one naphthyl group. In a preferred embodiment of the present invention, the cyanopyridyl group is not substituted with either a phenyl group or a naphthyl group. In one aspect of the present invention, A has at least one deuterium atom. In one aspect of the present invention, the 2-cyanophenyl group, 4-cyanophenyl group, and cyanopyridyl group which may be substituted with a phenyl group or a naphthyl group represented by A, have all hydrogen atoms present in these groups substituted with deuterium atoms.

[0016] The following are specific examples of groups that can be used for A in general formula (1). However, the A that can be used in the present invention is not limited to the following examples. In the following examples, * indicates a bond position, and C6D5 represents a phenyl group in which all hydrogen atoms have been deuterized.

[0017] [ka] JPEG2023107436000005.jpg240170JPEG2023107436000006.jpg227170JPEG2023107436000007.jpg112170

[0018] We disclose A1(D) to A95(D) in which all hydrogen atoms in A1 to A95 above are replaced with deuterium atoms. In one 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 One of them represents an acceptor group. In one aspect of the present invention, R 2 is an acceptor group. In one aspect of the present invention, R 3 This is the acceptor group. R 2 and R 3The acceptor group that can be adopted may be a 2-cyanophenyl group, a 4-cyanophenyl group, or a cyanopyridyl group which may be substituted with a phenyl group or a naphthyl group (the hydrogen atoms of these groups may be substituted with deuterium atoms). For a description of these groups and their preferred ranges, 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, A and R 2 Are A and R the same group? 3 These are the same group. In one aspect of the present invention, R 2 and R 3 One of them is a cyanopyridyl group which may be substituted with a 2-cyanophenyl group, a 4-cyanophenyl group, or a phenyl group or a naphthyl group (the hydrogen atoms of these groups may be substituted with deuterium atoms), but is a different group from A. In one aspect of the present invention, R 2 and R 3 One of the groups is an acceptor group, but it is not a 2-cyanophenyl group, a 4-cyanophenyl group, or a cyanopyridyl group which may be 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 with a positive Hammett σp value. The Hammett σp value, proposed by L.P. Hammett, quantifies the effect of substituents on the reaction rate or equilibrium of para-substituted benzene derivatives. Specifically, the following formula holds between substituents and the reaction rate constant or equilibrium constant in para-substituted benzene derivatives: log(k / k0) = ρσp or log(K / K0) = ρσp This is a constant (σp) specific to the substituent in the above equation. In the above equation, k0 is the rate constant of the unsubstituted benzene derivative, k is the rate constant of the substituted benzene derivative, K0 is the equilibrium constant of the unsubstituted benzene derivative, K is the equilibrium constant of the substituted benzene derivative, and ρ is the reaction constant determined by the type and conditions of the reaction. For an explanation of "Hammett's σp value" in this invention and the numerical values ​​of each substituent, refer to the description of σp value in Hansch, C. et. al., Chem. Rev., 91, 165-195 (1991). R 2 and R 3 The acceptor group that one of the components can adopt is preferably one with a σp of 0.3 or higher, more preferably 0.5 or higher, and even more preferably 0.7 or higher. For example, it may be selected from the range of 0.9 or higher, or from the range of 1.1 or higher.

[0020] Other acceptor groups besides 2-cyanophenyl groups, 4-cyanophenyl groups, or cyanopyridyl groups which may be substituted with phenyl or naphthyl groups (the hydrogen atoms of these groups may be substituted with deuterium atoms) include, for example, cyano groups. Other typical acceptor groups include heteroaryl groups which contain two or more nitrogen atoms as constituent atoms of the ring skeleton. For example, triazinyl groups and pyrimidinyl groups can be cited. 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 for example, unsubstituted aryl groups, preferably unsubstituted phenyl groups.

[0021] Specific examples of groups that can be adopted as acceptor groups of general formula (1) include A1 to A95 and A1(D) to A95(D) listed above. Other typical examples of acceptor groups are listed below. However, the acceptor groups that can be adopted in the present invention are not limited to the following examples. In the following examples, * indicates a bond position, and C6D5 represents a phenyl group in which all hydrogen atoms have been deuterated.

[0022] [ka]

[0023] In general formula (1), R 2 and R 3 The other side (i.e., the side that is not an acceptor group), R 1 , R 4 , R 5 At least one of these independently represents a substituted or unsubstituted benzoflo-fused carbazole-9-yl group, or a substituted or unsubstituted benzothieno-fused carbazole-9-yl group (hereinafter collectively referred to as "fused carbazole-9-yl group"). 1 ~R 5 The number of fused carbazole-9-yl groups is 1 to 4, for example 1 to 3, or for example 1 or 2. The number of fused carbazole-9-yl groups may be 2 to 4, or 2 or 3. In a group of the present invention, R 3 is an acceptor group, R 1 , R 2 , R 4 , R 5 At least one of them is independently a fused carbazole-9-yl group. In one aspect of the present invention, R 2 is a fused carbazole-9-yl group. In one aspect of the present invention, R 2 Only the fused carbazole-9-yl group. In a preferred embodiment of the present invention, R 2 and R 5is a fused carbazole-9-yl group. In one preferred embodiment of the present invention, R 2 and R 5 Only the fused carbazole-9-yl group. In a preferred embodiment of the present invention, R 2 , R 4 , R 5 is a fused carbazole-9-yl group. In one aspect of the present invention, R 1 ~R 4 This is a fused carbazole-9-yl group. In another group of the present invention, R 2 is an acceptor group, R 1 , R 3 , R 4 , R 5 At least one of these independently represents a fused carbazole-9-yl group. In one aspect of the present invention, R 1 is a fused carbazole-9-yl group. In one aspect of the present invention, R 3 is a fused carbazole-9-yl group. In one aspect of the present invention, R 4 is a fused carbazole-9-yl group. In one aspect of the present invention, R 5 is a fused carbazole-9-yl group. In one aspect of the present invention, R 3 Only the fused carbazole-9-yl group. In one aspect of the present invention, R 4 Only the fused carbazole-9-yl group. In one aspect of the present invention, R 5 Only the fused carbazole-9-yl group. In a preferred embodiment of the present invention, R 3 and R 5 is a fused carbazole-9-yl group. In one aspect of the present invention, R 3 and R 4 is a fused carbazole-9-yl group. In one aspect of the present invention, R 4 and R 5 is a fused carbazole-9-yl group. In one preferred embodiment of the present invention, R 3 and R 5 Only the fused carbazole-9-yl group. In a preferred embodiment of the present invention, R 3 ~R 5 is a fused carbazole-9-yl group. In one aspect of the present invention, R1 , R 3 , R 4 , R 5 This is a fused carbazole-9-yl group. When multiple fused carbazole-9-yl groups are present, in one preferred embodiment of the present invention, these fused carbazole-9-yl groups are identical. In one embodiment of the present invention, these fused carbazole-9-yl groups are different from each other. In one preferred embodiment of the present invention, the fused carbazole-9-yl group is a benzofloxic fused carbazole-9-yl group. In one embodiment of the present invention, the fused carbazole-9-yl group is a benchienone fused carbazole-9-yl group.

[0024] In the present invention, the benzoflo[2,3-a]carbazole-9-yl group can be used as the benzoflo-fused carbazole-9-yl group. Alternatively, the benzoflo[3,2-a]carbazole-9-yl group can be used. Furthermore, the benzoflo[2,3-b]carbazole-9-yl group can be used. Also, the benzoflo[3,2-b]carbazole-9-yl group can be used. Furthermore, the benzoflo[2,3-c]carbazole-9-yl group can be used. Also, the benzoflo[3,2-c]carbazole-9-yl group can be used. A preferred benzofuran-fused carbazole-9-yl group is a carbazole-9-yl group in which only one benzofuran ring is fused at the 2,3 positions, and no other rings are fused. Specifically, it is a group having one of the following structures, in which at least one hydrogen atom may be substituted. [ka]

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

[0026] The substituents of the fused carbazole-9-yl group may be selected from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E. In one preferred embodiment of the present invention, the fused carbazole-9-yl group is unsubstituted. In one preferred embodiment of the present invention, the substituents of the fused carbazole-9-yl group are substituted with unsubstituted aryl groups. In one embodiment of the present invention, the substituents of the fused carbazole-9-yl group are substituted with unsubstituted alkyl groups. The "aryl group" may be a monoring or a fused ring formed by the fusion of two or more rings. If it 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 rings include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, and a triphenylene ring. In one aspect of the present invention, the aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthalene-1-yl group, or a substituted or unsubstituted naphthalene-2-yl group, and is 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 aspect of the present invention, the substituent of the aryl group is one or more selected from the group consisting of alkyl groups, aryl groups, and deuterium atoms. In a preferred aspect of the present invention, the aryl group is unsubstituted. The alkyl group may be linear, branched, or cyclic. Furthermore, two or more of the linear, cyclic, and branched portions may be mixed. The number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. Also, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less. Specific examples of alkyl groups 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 groups. The alkyl group substituent may further be substituted with, for example, a deuterium atom, an aryl group, an alkoxy group, an aryloxy group, or a halogen atom. In one aspect of the present invention, the substituents of the alkyl group are one or more selected from the group consisting of aryl groups and deuterium atoms. In a preferred aspect of the present invention, the alkyl group is unsubstituted. The number of substituents substituted on the fused carbazole-9-yl group is preferably 1 to 10, more preferably 1 to 6, even more preferably 1 to 4, and may be, for example, 1 or 2. In one preferred embodiment of the present invention, either the 3rd or 6th position of the fused carbazole-9-yl group is substituted. In one preferred embodiment of the present invention, there is at least one substituent at the para position of the benzene ring with respect to the heteroatom present in the fused carbazole-9-yl group. In one preferred embodiment of the present invention, there is at least one substituent only at the para position of the benzene ring with respect to the heteroatom present in the ring-fused carbazole-9-yl group. In one preferred embodiment of the present invention, substituents are present at all of the substituted para positions of the benzene ring with respect to the heteroatom present in the ring-fused carbazole-9-yl group.

[0027] Specific examples of substituted or unsubstituted benzoflo-fused carbazole-9-yl groups, or substituted or unsubstituted benzothieno-fused carbazole-9-yl groups (i.e., fused carbazole-9-yl groups) that can be used in general formula (1) are shown below. However, the fused carbazole-9-yl groups that can be used in the present invention are not limited to the following specific examples. In the following specific examples, * indicates the bond position, Ph represents a phenyl group, and C6D5 represents a phenyl group in which all hydrogen atoms have been deuterated. Also, the methyl group is omitted from the notation. For example, D7 to D18 have a methyl group.

[0028] [ka] JPEG2023107436000012.jpg247170JPEG2023107436000013.jpg249170JPEG2023107436000014.jpg220168JPEG202 3107436000015.jpg255169JPEG2023107436000016.jpg222170JPEG2023107436000017.jpg229164JPEG2023107436 000018.jpg243170JPEG2023107436000019.jpg233164JPEG2023107436000020.jpg228163JPEG2023107436000021. jpg255167JPEG2023107436000022.jpg244170JPEG2023107436000023.jpg226170JPEG2023107436000024.jpg21317 0JPEG2023107436000025.jpg248158JPEG2023107436000026.jpg227170JPEG2023107436000027.jpg225170JPEG20 23107436000028.jpg253170JPEG2023107436000029.jpg243170JPEG2023107436000030.jpg201170JPEG2023107436 000031.jpg235164JPEG2023107436000032.jpg222170JPEG2023107436000033.jpg248170JPEG2023107436000034. jpg239166JPEG2023107436000035.jpg221170JPEG2023107436000036.jpg253170JPEG2023107436000037.jpg53163

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

[0030] The remaining R in the 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-condensed ring carbazol-9-yl group, and a substituted or unsubstituted benzothieno-condensed ring carbazol-9-yl group). The "remaining R 1 ~R 5 " referred to here means those that are neither an acceptor group, a substituted or unsubstituted benzofuro-condensed ring carbazol-9-yl group, nor a substituted or unsubstituted benzothieno-condensed ring carbazol-9-yl group). The remaining R 1 ~R 5 The number of is 0 to 3. In one aspect of the present invention, the remaining R 1 ~R 5is a hydrogen atom or a deuterium atom. In one aspect of the present invention, the remaining R 1 ~R 5 This includes substituted or unsubstituted aryl groups. In one aspect of the present invention, the remaining R 1 ~R 5 is a donor group. In one aspect of the present invention, the remaining R 1 ~R 5 All of them are donor groups. In one aspect of the present invention, the remaining R 1 ~R 5 is a hydrogen atom, a deuterium atom, or a donor group. In one aspect of the present invention, the remaining R 1 ~R 5 is a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl group. In one aspect of the present invention, the remaining R 1 ~R 5 It contains deuterium atoms.

[0031] Remaining R 1 ~R 5 For a description of the substituted or unsubstituted aryl groups that can be adopted and their preferred ranges, refer to the above description of aryl groups as substituents on the fused carbazole-9-yl group and their preferred ranges. In one aspect of the present invention, the remaining R 1 ~R 5 The substituted or unsubstituted aryl group that can be adopted is an unsubstituted aryl group, preferably an unsubstituted phenyl group. However, the remaining R 1 ~R 5 The aryl groups that can be formed are not substituted with cyano groups.

[0032] Remaining R 1 ~R 5 The donor groups that can be adopted can be selected from groups with a negative Hammett σp value. 1 ~R 5 The donor group that can be adopted is preferably one with a σp of -0.3 or less, more preferably -0.5 or less, and even more preferably -0.7 or less. For example, it may be selected from the range of -0.9 or less, or from the range of -1.1 or less. Remaining R 1 ~R 5When the number of donor groups adopted is two or more, it is preferable that all of those donor groups are the same. In one aspect of the present invention, the two or more donor groups are all different from each other. Remaining R 1 ~R 5 The donor group that can be adopted is preferably a group containing a substituted amino group. It may be a substituted amino group, an aryl group to which a substituted amino group is attached, and in particular a phenyl group to which a substituted amino group is attached. In one 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, and the two heteroaryl groups constituting the diheteroarylamino group may be bonded to each other. For a description of the aryl group and alkyl group and their preferred range, refer to the description of the aryl group and alkyl group as substituents of the fused carbazole-9-yl group and their preferred range described above. The "heteroaryl group" here may be a monoring or a fused ring formed by the fusion of two or more rings. 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 rings include pyridine rings and pyrimidine rings, and these rings may have other rings fused to them. Specific examples of heteroaryl groups include 2-pyridyl groups, 3-pyridyl groups, and 4-pyridyl groups. The number of constituent atoms of the ring skeleton of the heteroaryl group is preferably 4 to 40, more preferably 5 to 20, and may be selected within the range of 5 to 14 or within the range of 5 to 10.

[0033] Remaining R1 ~R 5 The donor group that can be formed is preferably a substituted or unsubstituted carbazole-9-yl group (excluding substituted or unsubstituted benzoflo-fused carbazole-9-yl groups and substituted or unsubstituted benzothieno-fused carbazole-9-yl groups). In one aspect of the present invention, the two benzene rings constituting the carbazole-9-yl group may have further fused benzene rings. In one aspect of the present invention, the two benzene rings constituting the carbazole-9-yl group may have further fused pyridine rings. In one aspect of the present invention, at least one of the ring skeleton constituent carbon atoms constituting the carbazole-9-yl group is substituted with a nitrogen atom. If substituted, it is preferable that one ring skeleton constituent carbon atom per benzene ring is substituted with a nitrogen atom. It is also preferable that one ring skeleton constituent carbon atom in the entire donor group is substituted with a nitrogen atom. The substituents of the carbazole-9-yl group may be selected from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E. In one preferred embodiment of the present invention, the remaining R 1 ~R 5 The carbazole-9-yl group that can be formed may be fused, but the hydrogen atoms are not substituted. In one preferred embodiment of the present invention, the fused carbazole-9-yl group is substituted with an unsubstituted aryl group. In one embodiment of the present invention, the fused carbazole-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 adopted are shown below. However, the donor groups that can be adopted in the present invention are not limited to the following examples. In the following examples, * indicates the bond position. Methyl groups are omitted from the notation, so for example, Z2 has one methyl group. [ka] JPEG2023107436000039.jpg82170

[0035] The results obtained by substituting all hydrogen atoms in Z1 to Z36 above with deuterium atoms are disclosed as Z1(D) to Z36(D). In one aspect of the present invention, the remaining R of general formula (1) 1 ~R 5 The donor groups that can be adopted are selected from the group consisting of Z1 to Z36. In one aspect of the present invention, the remaining R of general formula (1) 1 ~R 5 The donor groups that can be adopted are selected from the group consisting of Z1 to Z6. In one aspect of the present invention, the remaining R of general formula (1) 1 ~R 5 The donor groups that can be adopted are 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 They do not combine with each other to form a ring structure. In one 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 line-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 aspect of the present invention, the compound represented by general formula (1) contains at least one deuterium atom. In one aspect of the present invention, it has a deuterated alkyl group (e.g., a deuterated methyl group, a deuterated ethyl group, a deuterated cyclohexyl group). In one aspect of the present invention, it has a deuterated aryl group (e.g., a deuterated phenyl group). In one aspect 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 composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms. In one preferred embodiment of the present invention, the compound represented by general formula (1) is composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and oxygen atoms. Alternatively, the compound represented by general formula (1) may be composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms. The compound represented by general formula (1) may be composed only of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, and nitrogen atoms. Furthermore, the compound represented by general formula (1) may be a compound that does not contain hydrogen atoms but contains deuterium atoms.

[0039] In this specification, "substituent group A" refers to a hydroxyl group, halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, iodine atom), alkyl group (e.g., C1-40), alkoxy group (e.g., C1-40), alkylthio group (e.g., C1-40), aryl group (e.g., C6-30), aryloxy group (e.g., C6-30), arylthio group (e.g., C6-30), heteroaryl group (e.g., C5-30), heteroaryloxy group (e.g., C5-30), and This refers to one or more groups selected from the group consisting of teloarylthio groups (e.g., 5-30 ring skeleton atoms), acyl groups (e.g., 1-40 carbon atoms), alkenyl groups (e.g., 1-40 carbon atoms), alkynyl groups (e.g., 1-40 carbon atoms), alkoxycarbonyl groups (e.g., 1-40 carbon atoms), aryloxycarbonyl groups (e.g., 1-40 carbon atoms), heteroaryloxycarbonyl groups (e.g., 1-40 carbon atoms), silyl groups (e.g., trialkylsilyl groups with 1-40 carbon atoms), and nitro groups. In this specification, "substituent group B" means one or more groups selected from the group consisting of alkyl groups (e.g., 1 to 40 carbon atoms), alkoxy groups (e.g., 1 to 40 carbon atoms), aryl groups (e.g., 6 to 30 carbon atoms), aryloxy groups (e.g., 6 to 30 carbon atoms), heteroaryl groups (e.g., 5 to 30 atoms in the ring skeleton), heteroaryloxy groups (e.g., 5 to 30 atoms in the ring skeleton), and diarylaminoamino groups (e.g., 0 to 20 carbon atoms). In this specification, "substituent group C" means one or more groups selected from the group consisting of alkyl groups (e.g., 1 to 20 carbon atoms), aryl groups (e.g., 6 to 22 carbon atoms), heteroaryl groups (e.g., 5 to 20 atoms in the ring skeleton), and diarylamino groups (e.g., 12 to 20 carbon atoms). In this specification, "substituent group D" means one or more groups selected from the group consisting of alkyl groups (e.g., 1 to 20 carbon atoms), aryl groups (e.g., 6 to 22 carbon atoms), and heteroaryl groups (e.g., 5 to 20 atoms in the ring skeleton). In this specification, "substituent group E" means one group or a combination of two or more groups selected from the group consisting of alkyl groups (e.g., C1 to C20) and aryl groups (e.g., C6 to C22). In this specification, when a substituent is described as "substituent" or "substituted or unsubstituted," it may be selected from, for example, substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E.

[0040] Tables 1 and 2 below illustrate specific examples of compounds represented by general formula (1). However, the compounds represented by general formula (1) that can be used in the present invention should not be interpreted as being limited by these examples. In Tables 1 and 2, A and R of general formula (1) below are shown. 1 ~R 5 By identifying each compound individually, the structures of compounds 1 to 24786 are shown separately.

[0041] In Table 2, Ph represents a phenyl group. Table 2 shows A and R of multiple compounds in each row. 1 ~R 5 By displaying them together, the structures of compounds 1 to 24786 are shown. For example, in the row for compounds 1 to 459 in Table 2, A and R 3 A1, R 1 and R 4 It is fixed to Z1, R 2 and R 5 Compounds that are the same and have the same D1-D459 are designated as Compounds 1-459 in order. That is, the row for Compounds 1-459 in Table 2 is a collective display of Compounds 1-459 identified in Table 1. Similarly, in the row for Compounds 460-918 in Table 2, A and R 3 A1, R 1 and R 4 It is fixed to Z6, R 2 and R 5 Compounds with the same D1-D459 are designated as compounds 460-918, respectively. Compounds 919-8262 in Table 2 were identified using the same procedure. Compounds 8263-16524 in Table 2 are R 3 and R 5 It identifies compounds that are the same and belong to the D1-D459 group. For example, in the row for compounds 8263-8721 in Table 2, A and R 2 A1, R 1 is a hydrogen atom (H), R 4 It is fixed to Z1, R 3 and R 5 Compounds with the same D1-D459 are designated as compounds 8263-8721, respectively. Compounds 16525-20655 in Table 2 are R 3 ~R 5 It identifies compounds that are the same and belong to the D1-D459 group. For example, in the row of compounds 16525-16983 in Table 2, A and R 2 A1, R 1 R is fixed to the hydrogen atom (H), 3 ~R 5Compounds with the same D1-D459 are designated as compounds 16525-16983, respectively. Compounds 20656-24786 in Table 2 are R 3 and R 5 It identifies compounds that are the same and belong to the D1-D459 group. For example, in the row of compounds 20656-21114 in Table 2, A and R 2 A1, R 1 is a hydrogen atom (H), R 4 It is fixed to a phenyl group (Ph), and R 3 and R 5 Compounds with the same D1-D459 are designated as compounds 20656-21114, respectively. [Table 1] JPEG2023107436000041.jpg235161JPEG2023107436000042.jpg236161JPEG2023107436000043.jpg23416 0JPEG2023107436000044.jpg239163JPEG2023107436000045.jpg239163JPEG2023107436000046.jpg9656 [Table 2] JPEG2023107436000048.jpg55164

[0042] Compounds 1(D) to 24786(D) are disclosed in which all hydrogen atoms in the molecules of the above compounds 1 to 24786 are replaced with deuterium atoms. All compounds identified by the above numbers are disclosed individually. Furthermore, if rotational isomers exist for any of the above specific compound examples, both the mixture of rotational isomers and each separated rotational isomer are disclosed herein.

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

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

[0045] The molecular weight of the compound represented by general formula (1) is preferably 1500 or less, more preferably 1200 or less, even more preferably 1000 or less, and even more preferably 900 or less, when the organic layer containing the compound represented by general formula (1) is intended to be used by forming a film by vapor deposition. The lower limit of the molecular weight is the molecular weight of the smallest compound represented by general formula (1). Compounds represented by general formula (1) may be deposited as films by coating methods regardless of their molecular weight. Coating methods allow for the deposition of even relatively large molecular weight compounds. Compounds represented by general formula (1) have the advantage of being readily soluble in organic solvents. Therefore, coating methods are easily applied to compounds represented by general formula (1), and their purity can be easily increased through purification.

[0046] Applying the present invention, it is also conceivable to use a compound containing multiple structures represented by general formula (1) within its molecule as a light-emitting material. For example, one could consider using a polymer obtained by polymerizing a polymerizable group that is already present in the structure represented by general formula (1) as a light-emitting material. For instance, one could prepare a monomer containing a polymerizable functional group at any part of general formula (1), polymerize it alone or copolymerize it with other monomers to obtain a polymer having repeating units, and then use that polymer as a light-emitting material. Alternatively, one could consider coupling compounds having the structure represented by general formula (1) to obtain dimers or trimers, and then using those as light-emitting materials.

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

[0048] In the general formula above, Q represents a group containing the structure represented by general formula (1), and L 1 and L 2 The symbol 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 It is preferable that the structure is represented by -. Here, X 11L represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. 11 The group 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 or a substituted or unsubstituted phenylene group having 1 to 10 carbon atoms. In the general formula above, R 101 , R 102 , R 103 and R 104 Each of these independently represents a substituent. Preferably, these are 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, these are an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, or a chlorine atom; and even more preferably, these are 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 can bond to any part of the general formula (1) that constitutes Q. Two or more linking groups may be linked to a single Q to form a cross-linked structure or a network structure.

[0049] As a concrete example of a repeating unit structure, we can cite the structure represented by the following formula. [ka]

[0050] Polymers having repeating units including these formulas can be synthesized by introducing a hydroxyl group to any of the sites in general formula (1), reacting it with the following compounds as a linker to introduce polymerizable groups, and then polymerizing those polymerizable groups. [ka]

[0051] A polymer containing a structure represented by general formula (1) within its molecule may consist only of repeating units having the structure represented by general formula (1), or it may contain repeating units having other structures. Furthermore, the repeating units having the structure represented by general formula (1) contained in the polymer may be of a single type or two or more types. Examples of repeating units that do not have the structure represented by general formula (1) include those derived from monomers commonly used in copolymerization. For example, repeating units derived from monomers having ethylenically unsaturated bonds, such as ethylene and styrene, can be cited.

[0052] In one embodiment, 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 that can emit delayed fluorescence. In some embodiments of this disclosure, a compound represented by general formula (1) can emit light in the UV region, the blue region of the visible spectrum (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) 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 some embodiments of this disclosure, a compound represented by general formula (1) can emit light in the ultraviolet spectral region (e.g., 280-400 nm) when excited by thermal or electronic means. In some embodiments of this disclosure, organic semiconductor devices can be fabricated using a compound represented by general formula (1). The organic semiconductor device referred to here may be an organic photoelectric device that involves light, or an organic device that does not involve light. The organic photoelectric device may be an organic light-emitting device that emits light, an organic photodetector that receives light, or a device that generates energy transfer by light within the device. In some embodiments of this disclosure, organic photoelectric devices such as organic electroluminescent devices and solid-state image sensors (e.g., CMOS image sensors) can be fabricated using a compound represented by general formula (1). In some embodiments of this disclosure, CMOS (complementary metal-oxide-semiconductor) and the like can be fabricated using a compound represented by general formula (1).

[0053] The electronic properties of small molecule chemical libraries can be calculated using known ab initio quantum chemical calculations. For example, the Hartree-Fock equation (TD-DFT / B3LYP / 6-31G*) can be analyzed using time-dependent density functional theory with 6-31G*, Becke's three parameters, and a group of functions known as the Lee-Yang-Parr hybrid functional as a basis, to screen for molecular fragments (parts) with HOMO above a certain threshold and LUMO below a certain threshold. As a result, for example, when there is a HOMO energy (e.g., ionization potential) of -6.5 eV or higher, the donor portion ("D") can be selected. Also, for example, when there is a LUMO energy (e.g., electron affinity) of -0.5 eV or lower, the acceptor portion ("A") can be selected. The bridge portion ("B") is a strongly conjugated system that can strictly restrict the acceptor and donor portions to specific stereochemistrys, thereby preventing duplication between the π-conjugated systems of the donor and acceptor portions. In one embodiment, the compound library is selected using one or more of the following characteristics: 1. Emission near a specific wavelength 2. The calculated triplet states above a specific energy level. 3. ΔE below a specific value STValue 4. Quantum yield above a specific value 5. HOMO level 6. LUMO level In certain embodiments, the difference (ΔE ST ) between the lowest singlet excited state and the lowest triplet excited state at 77 K 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 certain embodiments, the ΔE ST 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 compound represented by General Formula (1) exhibits a quantum yield of more than 25%, such as 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] [Synthesis method of the compound represented by General Formula (1)] The compound represented by General Formula (1) includes novel compounds. The compound represented by General Formula (1) can be synthesized by combining known reactions. For example, by reacting A 1 with benzene having an acceptor group, a compound of General Formula (1) having a benzofuro-fused carbazole-9-yl group or a benzothieno-fused carbazole-9-yl group can be synthesized by reacting with benzofuro-fused carbazole or benzothieno-fused carbazole. For details of the reaction conditions, reference can be made to the synthesis examples described later.

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

[0056] [Film formation] In one embodiment, a film containing the compound represented by general formula (1) can be formed by a wet process. In the wet process, a solution containing the compound of the present invention is applied to a surface, and the film is formed after the solvent is removed. Examples of wet processes include, but are not limited to, spin coating, slit coating, inkjet (spray) printing, gravure printing, offset printing, and flexographic printing. In the wet process, a suitable organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In one embodiment, substituents (e.g., alkyl groups) that increase the solubility in organic solvents can be introduced into the compound contained in the composition. In certain embodiments, the film containing the compound of the present invention can be formed by a dry process. In certain embodiments, a vacuum evaporation method can be employed as the dry process, but it is not limited thereto. When the vacuum evaporation method is employed, the compounds constituting the film may be co-evaporated from individual evaporation sources, or may be co-evaporated from a single evaporation source in which the compounds are mixed. When using a single evaporation source, a mixed powder obtained by mixing the compound powders may be used, a compression molded body obtained by compressing the mixed powder may be used, or a mixture obtained by heating and melting each compound and then cooling it may be used. In certain embodiments, by performing co-evaporation under the condition that the evaporation rates (weight loss rates) of the plurality of compounds contained in a single evaporation source are the same or substantially the same, a film having a composition ratio corresponding to the composition ratio of the plurality of compounds contained in the evaporation source can be formed. If a plurality of compounds are mixed at the same composition ratio as the composition ratio of the formed film to form an evaporation source, a film having a desired composition ratio can be easily formed. In certain embodiments, the temperature at which each co-evaporated compound has the same weight loss rate can be specified and adopted as the temperature during co-evaporation.

[0057] [Examples of the use of the compound represented by the general formula (1)] The compound represented by the general formula (1) is useful as a material for organic light-emitting elements. It is particularly preferably used for organic light-emitting diodes and the like. Organic light-emitting diode: One aspect of the present invention relates to the use of a compound represented by general formula (1) as a light-emitting material for an organic light-emitting device. In some embodiments, the compound represented by general formula (1) can be effectively used as a light-emitting material in the light-emitting layer of an organic light-emitting device. In some embodiments, the compound represented by general formula (1) includes a delayed fluorescence (delayed phosphor) that emits delayed fluorescence. In some embodiments, the present invention provides a delayed phosphor having the 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 phosphor. 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 light-emitting materials, the light-emitting materials may be fluorescent materials, phosphorescent materials or TADFs. 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 generating delayed fluorescence from a compound represented by general formula (1). In some embodiments, an organic light-emitting device containing the compound as a light-emitting material emits delayed fluorescence and exhibits high light emission efficiency. In one embodiment, the light-emitting layer contains a compound represented by general formula (1), and the compound represented by general formula (1) is oriented parallel to the substrate. In one embodiment, the substrate is a film-forming surface. In one embodiment, the orientation of the compound represented by general formula (1) relative to the film-forming surface affects or determines the direction of propagation of light emitted by the aligned compound. In one embodiment, the light extraction efficiency from the light-emitting layer is improved by aligning the direction of propagation of light emitted by the compound represented by general formula (1). One aspect of the present invention relates to an organic light-emitting device. In one embodiment, the organic light-emitting device includes a light-emitting layer. In one embodiment, the light-emitting layer includes a compound represented by general formula (1) as a light-emitting material. In one embodiment, the organic light-emitting device is an organic photoluminescent device (organic PL device). In one embodiment, the organic light-emitting device is an organic electroluminescent device (organic EL device). In one embodiment, the compound represented by general formula (1) assists the light emission of other light-emitting materials included in the light-emitting layer (as a so-called assist dopant). In one embodiment, the compound represented by general formula (1) included in the light-emitting layer is at its lowest excited singlet energy level and is located between the lowest excited singlet energy level of the host material included in the light-emitting layer and the lowest excited singlet energy level of the other light-emitting materials included in the light-emitting layer. In some embodiments, the organic photoluminescent element includes at least one light-emitting layer. In some embodiments, the organic electroluminescent element 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 a light-emitting layer. In some embodiments, the organic layer includes only a 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 hole transport layers, hole injection layers, electron barrier layers, hole barrier layers, electron injection layers, electron transport layers, and exciton barrier layers. In some embodiments, the hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function.

[0058] Light-emitting layer: In one embodiment, the light-emitting layer is a layer in which holes and electrons injected from the anode and cathode, respectively, recombine to form excitons. In another embodiment, the layer emits light. In some embodiments, only the light-emitting material is used as the light-emitting layer. In some embodiments, the light-emitting layer includes the light-emitting material and a host material. In some embodiments, the light-emitting material is one or more compounds represented by general formula (1). In some embodiments, singlet and triplet excitons generated in the light-emitting material are confined within the light-emitting material in order to improve the light emission efficiency of organic electroluminescent elements and organic photoluminescent elements. In some embodiments, a host material is used in addition to the light-emitting material in the light-emitting layer. In some embodiments, the host material is an organic compound. In some embodiments, the organic compound has excitation singlet energy and excitation triplet energy, at least one of which is higher than those of the light-emitting material of the present invention. In some embodiments, singlet and triplet excitons generated in the light-emitting material of the present invention are confined within the molecules of the light-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, a host material that can achieve high light emission efficiency without being sufficiently confined, i.e., a host material that can achieve high light emission efficiency, even though high light emission efficiency can still be obtained, can be used in the present invention without particular limitation. 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 synchrotron radiation includes both fluorescence and delayed fluorescence. In some embodiments, the synchrotron radiation includes synchrotron radiation from a host material. In some embodiments, the synchrotron radiation consists of synchrotron radiation from a host material. In some embodiments, the synchrotron radiation includes synchrotron radiation from a compound represented by general formula (1) and synchrotron radiation from a host material. In some embodiments, a TADF molecule and a host material are used. In some embodiments, the TADF is an assist dopant, having a lower excitation singlet energy than the host material in the light-emitting layer and a higher excitation singlet energy than the light-emitting material in the light-emitting layer.

[0059] When a compound represented by general formula (1) is used as an assist dopant, various compounds can be used as the luminescent material (preferably a fluorescent material). Such luminescent materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyromethene derivatives, terphenyl derivatives, terphenylene derivatives, fluorantene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, duroridine derivatives, thiazole derivatives, and derivatives having metals (Al,Zn). These exemplary skeletons may or may not have substituents. Furthermore, these exemplary skeletons may be combined with each other. The following are examples of luminescent materials that can be used in combination with an assist dopant having the structure represented by general formula (1).

[0060] [ka] JPEG2023107436000054.jpg223161JPEG2023107436000055.jpg255168

[0061] Furthermore, the compounds described in paragraphs 0220-0239 of Publication No. WO2015 / 022974 can also be particularly preferred as luminescent materials used in conjunction with an assist dopant having a structure represented by general formula (1).

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

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

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

[0065] In general formula (E2), R 1 and R 2 Each of these 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 Each of these 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 These may be bonded to each other to form a ring structure. CR in general formula (1) 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 , CR10 , CR 11 , CR 12 , CR 13 , CR 14 , CR 15 , CR 16 This can be replaced with N.

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

[0067] In general formula (E3), Z 1 and Z 2 Each of these independently represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring, R 1 ~R 9 Each of these 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 They may be bonded to each other to form a ring structure. However, Z 1 , Z 2 , R 1 and R 2 A ring formed by the bonding of these elements, R 2 and R 3 A ring formed by the bonding of these elements, R 4 and R 5 A ring formed by the bonding of these elements, and R 5 and R 6 At least one of the rings formed by the bonding of these elements is a furan ring of a substituted or unsubstituted benzofuran, a thiophene ring of a substituted or unsubstituted benzothiophene, or a pyrrole ring of a substituted or unsubstituted indole, and R 1~R 9 at least one of which is a substituted or unsubstituted aryl group, or an acceptor group, or Z 1 and Z 2 at least one of which is a ring having an aryl group or an acceptor group as a substituent. Among the benzene ring skeleton constituent carbon atoms constituting the benzofuran ring, the benzothiophene ring, and the indole ring, the substitutable carbon atoms may be substituted with nitrogen atoms. C-R in the general formula (1) 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] Furthermore, as a more preferable light-emitting material, a compound represented by the following general formula (E4) can also be mentioned.

Chemical formula

[0069] In the general formula (E4), Z 1 represents a furan ring condensed with a substituted or unsubstituted benzene ring, a thiophene ring condensed with a substituted or unsubstituted benzene ring, or an N-substituted pyrrole ring condensed with a substituted or unsubstituted benzene ring, and Z 2 and Z 3 each independently represent a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, and R 1 represents a hydrogen atom, a deuterium atom or a substituent, and R 2 and R 3 each independently represent a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group. Z 1 and R 1 , R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3They may be bonded to each other to form a ring structure. However, R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one pair of these elements are joined together to form a ring structure.

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

[0071] In general formula (E5), R 1 and R 2 Each of these 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 of these independently represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring, R 3 ~R 9 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent. However, R 1 , R 2 , Z 1 and Z 2 At least one of these includes 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 These may be bonded to each other to form a cyclic structure. Substitutable carbon atoms among the benzene ring skeleton constituent carbon atoms of the benzofuran ring, the benzothiophene ring, and the indole ring may be substituted with nitrogen atoms. CR in general formula (1) 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 It may be replaced with N.

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

[0073] In general formula (E6), X 1 and X 2 In this case, one atom is a nitrogen atom and the other is a boron atom. 1 ~R 26 , A 1 , A 2 Each of these 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 They may be bonded to each other to form a ring structure. However, X 1 When R is a nitrogen atom, 17 and R 18 They bond to each other to form a single bond and create a pyrrole ring, X 2 When R is a nitrogen atom, 21 and R 22 They bond to each other to form a single bond and create a pyrrole ring. However, X 1 is a nitrogen atom, and R 7 and R 8 and R 21 and R 22 The nitrogen atoms bond to form a 6-membered ring, R 17 and R 18 When R is bonded to each other to form a single bond, 1 ~R 6 At least one of them 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 One of these elements is bonded to another to form an aromatic ring or a heteroaromatic ring.

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

[0075] In general formula (E7), R 201 ~R 221 Each of these independently represents a hydrogen atom, a deuterium atom, or a substituent, preferably 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 these is bonded to each other to form a benzophlo or benzothieno structure. Preferably, R 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 of the following pairs, and 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 these groups are bonded together to form a benzofloe or benzothieno structure. More preferably, R 203 and R 204 These combine with each other to form a benzofloxic structure or a benzothieno structure, and more preferably R 203 and R 204 , R 216 and R 217 These are bonded to each other to form a benzofloxacin or benzothieno structure. Particularly preferred is R 203 and R 204 , R 216 and R 217 These are bonded to each other to form a benzofloxacin or benzothieno structure, 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) as described in the specifications of Japanese Patent Applications Nos. 2021-103698, 2021-103699, 2021-103700, 2021-081332, 2021-103701, 2021-151805, and 2021-188860 can be used as luminescent materials. Descriptions of these general formulas (1) and specific compounds are incorporated herein by reference as part of this specification.

[0077] In one embodiment, when a host material is used, the amount of the compound of the present invention as a light-emitting material contained in the light-emitting layer is 0.1% by weight or more. In another embodiment, when a host material is used, the amount of the compound of the present invention as a light-emitting material contained in the light-emitting layer is 1% by weight or more. In another embodiment, when a host material is used, the amount of the compound of the present invention as a light-emitting material contained in the light-emitting layer is 50% by weight or less. In another embodiment, when a host material is used, the amount of the compound of the present invention as a light-emitting material contained in the light-emitting layer is 20% by weight or less. In another embodiment, when a host material is used, the amount of the compound of the present invention as a light-emitting material contained in the light-emitting layer is 10% by weight or less. In one embodiment, the host material of the light-emitting layer is an organic compound having hole transport and electron transport functions. In another embodiment, the host material of the light-emitting layer is an organic compound that prevents an increase in the wavelength of the synchrotron radiation. In yet another embodiment, the host material of the light-emitting layer is an organic compound having a high glass transition temperature.

[0078] In some embodiments, the host material is selected from the group consisting of: [ka] JPEG2023107436000064.jpg159164 In one embodiment, the light-emitting layer contains two or more structurally different TADF molecules. For example, the light-emitting layer can contain three materials in which the excited singlet energy levels are highest in the host material, followed by the first TADF molecule and then the second TADF molecule. In this case, both the first TADF molecule and the second TADF molecule have a difference ΔE between their lowest excited singlet energy level and their lowest excited triplet energy level of 77K. STThe luminescence voltage is 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 luminescent layer is preferably greater than the concentration of the second TADF molecules. Also, the concentration of the host material in the luminescent layer is preferably greater than the concentration of the second TADF molecules. The concentration of the first TADF molecules in the luminescent layer may be greater than, less than, or the same as the concentration of the host material. In one embodiment, the composition of the luminescent layer may be 10 to 70% by weight of the host material, 10 to 80% by weight of the first TADF molecules, and 0.1 to 30% by weight of the second TADF molecules. In one embodiment, the composition of the light-emitting layer may be 20-45% by weight of the host material, 50-75% by weight of the first TADF molecule, and 5-20% by weight of the second TADF molecule. In one embodiment, the photo-excited quantum emission yield φPL1(A) of a co-evaporated film of the first TADF molecule and the host material (concentration of the first TADF molecule in this co-evaporated film = A by weight) and the photo-excited quantum emission yield φPL2(A) of a co-evaporated film of the second TADF molecule and the host material (concentration of the second TADF molecule in this co-evaporated film = A by weight) satisfy the relationship φPL1(A)>φPL2(A). In another embodiment, the photo-excited quantum emission yield φPL2(B) of a co-evaporated film of the second TADF molecule and the host material (concentration of the second TADF molecule in this co-evaporated film = B by weight) and the photo-excited quantum emission yield φPL2(100) of a film of the second TADF molecule alone satisfy the relationship φPL2(B)>φPL2(100). In one embodiment, the light-emitting layer may contain three different structural TADF molecules. The compound of the present invention may be any of the multiple TADF compounds contained in the light-emitting layer. In some embodiments, the light-emitting layer may 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 any metallic elements. In some embodiments, the light-emitting layer may 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 may 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 may 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 fluorescence material. Preferred delayed fluorescence materials include paragraphs 0008-0048 and 0095-0133 of WO2013 / 154064, paragraphs 0007-0047 and 0073-0085 of WO2013 / 011954, paragraphs 0007-0033 and 0059-0066 of WO2013 / 011955, and paragraph 0008 of WO2013 / 081088. ~0071 and 0118~0133, paragraphs 0009~0046 and 0093~0134 of JP 2013-256490, paragraphs 0008~0020 and 0038~0040 of JP 2013-116975, paragraphs 0007~0032 and 0079~0084 of WO2013 / 133359, paragraph 0 of WO2013 / 161437 Paragraphs 008-0054 and 0101-0121 of Japanese Patent Publication No. 2014-9352, paragraphs 0007-0041 and 0060-0069 of Japanese Patent Publication No. 2014-9224, paragraphs 0008-0048 and 0067-0076 of Japanese Patent Publication No. 2017-119663, paragraphs 0013-0025 of Japanese Patent Publication No. 2017-119664, Japanese Patent Publication No. 2 This includes compounds included in the general formulas described in paragraphs 0012-0025 of Japanese Patent Publication No. 017-222623, paragraphs 0010-0050 of Japanese Patent Application Publication No. 2017-226838, paragraphs 0012-0043 of Japanese Patent Application Publication No. 2018-100411, and paragraphs 0016-0044 of Japanese Patent Application Publication No. WO2018 / 047853, particularly exemplary compounds that can emit delayed fluorescence.Furthermore, here we have Japanese Patent Publication No. 2013-253121, WO2013 / 133359, WO2014 / 034535, WO2014 / 115743, WO2014 / 122895, WO2014 / 126200, WO2014 / 136758, WO2014 / 133121, 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, Publications WO2015 / 072470, WO2015 / 108049, WO2015 / 080182, WO2015 / 072537, WO2015 / 080183, JP 2015-129240, WO2015 / 129714, WO2015 / 129715, WO2015 / 13350 A light-emitting material that can emit delayed fluorescence, as described in Publication No. 1, WO2015 / 136880, WO2015 / 137244, WO2015 / 137202, WO2015 / 137136, WO2015 / 146541, and WO2015 / 159541, can preferably be used. The above publications described in this paragraph are incorporated herein by reference as part of this specification.

[0079] The following describes each component of the organic electroluminescent element and each layer other than the light-emitting layer.

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

[0081] anode: In some embodiments, the anode of an organic electroluminescent apparatus is manufactured from a metal, alloy, conductive compound, or a combination thereof. In some embodiments, the metal, alloy, or conductive compound has a high work function (4 eV or more). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is selected from CuI, indium tin oxide (ITO), SnO2, and ZnO. In some embodiments, an amorphous material capable of forming a transparent conductive film, such as IDIXO (In2O3-ZnO), is used. In some embodiments, the anode is a thin film. In some embodiments, the thin film is manufactured by vapor deposition or sputtering. In some embodiments, the film is patterned by photolithography. In some embodiments, if the pattern does not need to be highly precise (e.g., about 100 μm or more), the pattern may be formed using a mask with a shape suitable for vapor deposition or sputtering onto the electrode material. In some embodiments, when a coating material such as an organic conductive compound can be applied, wet film formation methods such as printing or coating methods are used. In some embodiments, when synchrotron radiation passes through the anode, the anode has a transmittance of more than 10%, and the anode has a sheet resistance of several hundred ohms or less per unit area. In some embodiments, the thickness of the anode is 10 to 1,000 nm. In some embodiments, the thickness of the anode is 10 to 200 nm. In some embodiments, the thickness of the anode varies depending on the material used.

[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-injection metal), an alloy, a 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 the electron-injection metal and a second metal that is a stable metal having a higher work function than the electron-injection 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-injection properties and resistance to oxidation. In some embodiments, the cathode is manufactured by forming the electrode material as a thin film by vapor deposition or sputtering. In some embodiments, the cathode has a sheet resistance of several hundred ohms or less per unit area. In some embodiments, the thickness of the cathode is 10 nm to 5 μm. In some embodiments, the thickness of the cathode is 50 to 200 nm. In some embodiments, either the anode or cathode of the organic electroluminescent element is transparent or translucent in order to transmit synchrotron radiation. In some embodiments, a transparent or translucent electroluminescent element enhances the light radiance. In some embodiments, a transparent or translucent cathode is formed by forming the cathode with respect to the conductive transparent material described above. In some embodiments, the element includes an anode and a cathode, both of which are transparent or translucent.

[0083] Injection layer: The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer reduces the driving voltage and enhances the light radiance. In some embodiments, the injection layer includes a hole injection layer and an electron injection layer. The injection layer can be located between the anode and the light-emitting layer or hole transport layer, and between the cathode and the light-emitting layer or electron transport layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is absent. The following are examples of preferred compounds that can be used as hole injection materials.

[0084] [ka]

[0085] Next, we will list some examples of preferred compounds that can be used as electron injection materials. [ka]

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

[0087] Hole barrier layer: The hole barrier layer functions as an electron transport layer. In some embodiments, the hole barrier layer prevents holes from reaching the electron transport layer during electron transport. In some embodiments, the hole barrier layer increases the probability of electron-hole recombination in the light-emitting layer. The material used for the hole barrier layer may be the same material described above for the electron transport layer. The following are examples of preferred compounds that can be used in the hole barrier layer.

[0088] [ka]

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

[0090] [ka]

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

[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 the following properties: hole injection or transport properties and electron barrier 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, indrocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, aminosubstituted 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 given 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 have the function of transporting electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole barrier 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, thiopyrandioxide derivatives, carbodiimides, fluorenylidene methane derivatives, anthraquinodimethane, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives or combinations thereof, or polymers thereof. In some embodiments, the electron transport material is a thiadiazole inducer 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 preferred compounds that can be added to each organic layer are given. For example, they can be added as stabilizing materials.

[0097] [ka]

[0098] While specific examples of preferred materials that can be used in organic electroluminescent elements have been provided, the materials that can be used in the present invention are not limited to the following exemplary compounds. Furthermore, even compounds exemplified as materials with specific functions can be repurposed as materials with other functions.

[0099] device: In some embodiments, the light-emitting layer is incorporated into the device. For example, devices include, but are not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, mobile phones, and tablets. In some embodiments, the electronic device includes an OLED having an anode, a cathode, and at least one organic layer including a light-emitting layer between the anode and the cathode. In some embodiments, the components described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices. In some embodiments, the components may be useful for facilitating charge transfer or energy transfer within the device and / or as hole transport materials. Examples of such devices include 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 includes an OLED comprising an anode, a cathode, and at least one organic layer including a light-emitting 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 comprising combinations of OLEDs. In some embodiments, the combination of OLEDs is a combination of three colors (e.g., RGB). In some embodiments, the combination of OLEDs is a combination of colors other than red, green, and blue (e.g., orange and yellow-green). In some embodiments, the combination of OLEDs is a combination of two, four, or more colors. In some embodiments, the device is A circuit board having a first surface with a mounting surface and a second surface opposite to it, defining at least one opening, The mounting surface comprises at least one OLED having a light-emitting configuration, wherein the at least one OLED includes an anode, a cathode, and at least one organic layer comprising a light-emitting layer between the anode and the cathode, A housing for a circuit board, An OLED light comprising at least one connector located at the end of the housing, wherein the housing and the connector define a package suitable for mounting to a lighting fixture. In some embodiments, the OLED light has multiple OLEDs mounted on a circuit board such that light is emitted in multiple directions. In some embodiments, some of the light emitted in the 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 compound according to the present invention is deposited on a substrate using a process such as vacuum evaporation, deposition, vapor deposition, or chemical vapor deposition (CVD), but is not limited. In some embodiments, the substrate is a photoplate structure useful in two-sided etching, providing pixels with a unique aspect ratio. The screen (also called a mask) is used in the manufacturing process of an OLED display. The design of the corresponding artwork pattern allows for the arrangement of very steep, narrow tie bars between pixels in the vertical direction, as well as large, wide oblique apertures in the horizontal direction. This enables the fine pattern configuration of pixels required for high-resolution displays, while optimizing chemical vapor deposition on a TFT backplane. Internal patterning of pixels allows for the creation of three-dimensional pixel apertures with various aspect ratios in the horizontal and vertical directions. Furthermore, the use of imaged "stripes" or halftone circles within a pixel area protects etching in specific areas until these particular patterns are undercut and removed from the substrate. At that time, all pixel areas are processed at a similar etching rate, but the depth varies depending on the halftone pattern. By changing the size and spacing of the halftone patterns, etching with varying degrees of protection within the pixel becomes possible, enabling localized deep etching necessary to form steep vertical bevels. A preferred material for deposition masks is Invar. Invar is a metal alloy that is cold-rolled into long, thin sheets at steel mills. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask. A suitable and low-cost method for forming openings within a deposition mask is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel matrix on a substrate. In some embodiments, the screen or display pattern is fabricated using lithography (e.g., photolithography and e-beam lithography). In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In further embodiments, the screen or display pattern is fabricated using plasma etching.

[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, coating the TFT with a planarization film, sequentially forming pixel electrodes, an emissive layer, a counter electrode, and an encapsulation layer over time, and then cutting it from 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, coating the TFT with a planarization film, sequentially forming pixel electrodes, an emissive layer, a counter electrode, and an encapsulation layer over time, and then cutting it from the mother panel.

[0103] In another aspect of the present invention, a method for manufacturing an organic light-emitting diode (OLED) display is provided, the method being A process of forming a barrier layer on the base substrate of the mother panel, The process of forming multiple display units on the barrier layer in cell panel units, The process of forming an encapsulation layer on each of the display units of the cell panel, The process includes the step of applying an organic film to the interface portion between the cell panels. In some embodiments, the barrier layer is an inorganic film formed of, for example, SiNx, and the edges of the barrier layer are covered with an organic film formed of polyimide or acrylic. In some embodiments, the organic film assists in the soft cutting of the mother panel into cell panel units. In some embodiments, the thin-film transistor (TFT) layer includes a light-emitting layer, a gate electrode, and source / drain electrodes. Each of a 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, wherein the organic film coated on the interface portion is formed of the same material as the planarization film and is formed simultaneously with the formation of the planarization film. In some embodiments, the light-emitting unit is connected to the TFT layer by a passivation layer, a planarization film between them, 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 the display unit or the encapsulation layer.

[0104] Each of the organic film and the planarization film may contain either polyimide or 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 the steps of attaching a carrier substrate made of glass material to another surface of the base substrate before forming a barrier layer on one surface of the polyimide 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 placed on the TFT layer for coating 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 made of polyimide or acrylic, as is the organic film formed at the edges of the barrier layer. In some embodiments, the planarization film and the organic film are formed simultaneously during the manufacture of the OLED display. In some embodiments, the organic film may be formed at the edges of the barrier layer, so that a portion of the organic film is in direct contact with the base substrate, and the remaining portion of the organic film is in contact with the barrier layer while surrounding the edges of the barrier layer.

[0105] In some embodiments, the light-emitting layer includes a pixel electrode, a counter electrode, and an organic light-emitting layer disposed between the pixel electrode and the counter electrode. In some embodiments, the pixel electrode is connected to the source / drain electrodes of the TFT layer. In some embodiments, when a voltage is applied to the pixel electrode through the TFT layer, an appropriate voltage is formed between the pixel electrode and the counter electrode, causing the organic light-emitting layer to emit light, thereby forming an image. Hereinafter, an image forming unit having a TFT layer and a light-emitting unit will be referred to as a display unit. In some embodiments, the encapsulation layer covering the display unit and preventing the penetration of external moisture may be formed as a thin-film encapsulation structure in which organic films and inorganic films are alternately laminated. In some embodiments, the encapsulation layer has a thin-film encapsulation structure in which a plurality of thin films are laminated. In some embodiments, the organic film applied to the interface portion is spaced apart from each of the plurality of display units. In some embodiments, the organic film is formed such that a portion of the organic film is in direct contact with the base substrate, while the remaining portion of the organic film surrounds the edges of the barrier layer while also being in contact with the barrier layer.

[0106] In one embodiment, the OLED display is flexible and uses a flexible base substrate made of polyimide. In some embodiments, the base substrate is formed on a carrier substrate made of glass material, and then the carrier substrate is separated. In some embodiments, the 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 interface 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 portion, where a groove is formed in the barrier layer, and at least a portion of the organic film is formed in the groove, and the groove does not penetrate the base substrate. In some embodiments, a TFT layer is formed for each cell panel, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are placed on the TFT layer and cover the TFT layer. At the same time that a planarization film made of, for example, polyimide or acrylic is formed, the groove in the interface portion is covered with an organic film made of, for example, polyimide or acrylic. This prevents cracking by allowing the organic film to absorb the impact generated when each cell panel is cut along the groove at the interface portion. That is, if all barrier layers are completely exposed without an organic film, when each cell panel is cut along the groove at the interface portion, the impact generated is transmitted to the barrier layer, thereby increasing the risk of cracking. However, in one embodiment, the groove in the interface portion between barrier layers may be covered with an organic film to absorb the impact that would otherwise be transmitted to the barrier layer, so that each cell panel is cut softly and cracking in the barrier layer is prevented. In one embodiment, the organic film and the planarizing film covering the grooves of the interface portion are arranged with a gap between them. For example, if the organic film and the planarizing film are connected to each other as a single layer, there is a risk that external moisture may penetrate the display unit through the remaining parts of the planarizing film and organic film. Therefore, the organic film and the planarizing film are arranged with a gap between them so that the organic film is spaced away from the display unit.

[0108] In some embodiments, the display unit is formed by the formation of a light-emitting unit, and an encapsulation layer is placed on the display unit to cover it. This separates the carrier substrate supporting the base substrate from the base substrate after the mother panel is completely manufactured. In some embodiments, when a laser beam is emitted onto the carrier substrate, the carrier substrate is separated from the base substrate due to the difference in thermal expansion coefficients between the carrier substrate and the base substrate. In some embodiments, the mother panel is cut into cell panel units. In some embodiments, the mother panel is cut along the interface between cell panels using a cutter. In some embodiments, the grooves of the interface along which the mother panel is cut are covered with an organic film so that the organic film absorbs the impact during cutting. In some embodiments, cracking can be prevented in the barrier layer during cutting. In some embodiments, the method reduces the defect rate of the product and stabilizes its 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 coated on the edges of the barrier layer. [Examples]

[0109] The features of the present invention will be further described in detail below with reference to synthesis examples and embodiments. The materials, processing content, 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 interpreted as being limited by the specific examples shown below. The luminescence characteristics were evaluated using a source meter (Keithley Corporation: 2400 series), a semiconductor parameter analyzer (Agilent Technologies: E5273A), an optical power meter measuring device (Newport Corporation: 1930C), an optical spectrometer (Ocean Optics: USB2000), a spectroradiometer (Topcon Corporation: SR-3), and a streak camera (Hamamatsu Photonics K.K.: C4334). In the following synthesis examples, compounds included in general formula (1) were synthesized.

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

[0111] Compound A Under a nitrogen atmosphere, 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) was mixed with 1 M potassium carbonate aqueous solution (50 mL) and tetrakistriphenylphosphine palladium (0) (0.93 g, 0.81 mmol), and the mixture was stirred at 80 °C for 15 hours. The reaction solution was allowed to return to room temperature, extracted with chloroform, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation, and the mixture was purified by silica gel column chromatography (hexane:toluene = 1:4) to obtain 2.00 g (5.68 mmol, yield 35%) 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: Theoretical value 352.06, Observed value 353.22 [M+H + ]

[0112] Compound B Under a nitrogen atmosphere, 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 allowed to return 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, yield 67%) 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: Theoretical value 646.20, Observed value 647.48 [M+H + ]

[0113] compound 3 Under a nitrogen atmosphere, potassium carbonate (0.37 g, 2.71 mmol) was added to a solution of compound B (0.70 g, 1.08 mmol) and 5H-benzofl[3,2-C]carbazole (0.70 g, 2.71 mmol) in N,N-dimethylformamide (140 mL), and the mixture was stirred at 150 °C for 15 hours. The reaction mixture was allowed to return 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, yield 46%) 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: Theoretical value 1120.35, Observed value 1121.84 [M+H + ]

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

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

[0116] Compound D Compound C (3.84 g, 10.0 mmol) and 3-bromo-2-pyridinecarbonitride (4.21 g, 23.0 mmol) were dissolved in toluene / water (90 mL / 10 mL). 2-dicyclohexylphosphino-2′,6′-dimethoxysibiphenyl (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) were added under a nitrogen stream, and the mixture was stirred at room temperature for 15 hours. The mixture was allowed to return to room temperature, washed with saturated ammonium chloride aqueous solution and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was removed by distillation. This was purified by silica gel column chromatography (hexane:ethyl acetate = 2:1) to obtain compound D (0.51 g, 1.50 mmol, yield 15%) 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 Spectral Analysis: Theoretical value 336.06, Observed value 338.18

[0117] Compound 19281 and Compound E Under a nitrogen atmosphere, 2.26 g (8.80 mmol) of 5H-benzofl[3,2-c]carbazole and 1.66 g (12.0 mmol) of potassium carbonate were added to N,N-dimethylformamide (25 mL), and the mixture was 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, then the temperature was raised to 60°C and stirred for 24 hours. The reaction solution was allowed to return to room temperature, water was added, and the precipitate was filtered off. The filtered material was washed with methanol and vacuum dried. The residue was purified by silica gel column chromatography (toluene:ethyl acetate = 85:15) to obtain compound 19281 (1.32 g, 1.26 mmol, yield 32%) and compound E (0.89 g, 1.10 mmol, yield 27%) as pale yellow solids. 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 spectral analysis: Theoretical value 1047.30, Observed value 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 spectral analysis: Theoretical value 810.22, Observed value 811.39

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

[0119] Compound 13773 Under a nitrogen atmosphere, 9H-carbazole (0.33 g, 1.95 mmol) and potassium carbonate (0.31 g, 2.25 mmol) were mixed with 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 allowed to return to room temperature, water was added, and the precipitate was filtered off. The filtered material was washed with methanol and vacuum dried. The residue was purified by silica gel column chromatography (toluene:ethyl acetate = 98:2) to obtain compound 13773 (1.09 g, 1.14 mmol, yield 76%) 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 spectral analysis: Theoretical value 957.29, Observed value 958.46

[0120] Compounds 23430, 15609, 19740, 921, Reference Compound 1, and Reference Compound 2 were also synthesized using the same procedure as in Synthesis Examples 1-3. [ka]

[0121] (Example 1) Thin film fabrication and evaluation Vacuum deposition onto a quartz substrate, with a vacuum level of 1 × 10⁻⁶ -3 Compound 3 was deposited under conditions of less than Pa, forming a neat thin film of compound 3 with a thickness of 100 nm. Separately, using a vacuum deposition method on a quartz substrate, a vacuum of 1 × 10⁻¹⁰ -3 Compound 3 and PYD2Cz were deposited from different deposition sources under conditions below Pa, forming a doped thin film with a compound 3 concentration of 20% by weight and a thickness of 100 nm. Neat and doped thin films were formed in the same manner using compounds 13773 and 19281 instead of compound 3. The lowest excited singlet energy and lowest excited triplet energy were measured using each neat thin film that was formed, and the difference ΔE ST The values ​​were 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. Similarly, the maximum emission wavelengths for reference compound 1 and reference compound 2 were measured to be 458 nm and 469 nm, respectively. Compounds 3, 13773, 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 using the comparative compounds 1-4 listed below, according to the method described above. For comparative compounds 1-3, DPEPO was used as the host material. The delayed fluorescence lifetime was measured using the prepared doped thin films, including those of compound 3, compound 13773, and compound 19281. The results are shown in Table 4. [ka]

[0123] [Table 4]

[0124] Compounds 3, 13773, and 19281, represented by general formula (1), had shorter delayed fluorescence lifetimes than comparative compounds 1-3. Comparative compound 4 had a delayed fluorescence lifetime at a similar level to compound 13773, but its photoluminescence quantum yield (PLQY) was low at 26%, and it did not exhibit the superior luminescence properties seen in compounds 3, 13773, and 19281. Furthermore, the photoluminescence quantum yield (PLQY) of compounds 3, 13773, and 19281 was higher than that of comparative compounds 1 and 2, confirming their superior luminescence properties.

[0125] (Example 2) Fabrication of an organic electroluminescent device Each thin film is deposited onto a glass substrate with an anode made of indium tin oxide (ITO) with a thickness of 50 nm using a vacuum deposition method at a vacuum level of 5.0 × 10⁻⁶. -5The layers were stacked using Pa. First, HAT-CN was formed to a thickness of 10 nm on ITO, followed by NPD to a thickness of 35 nm, and then PTCz to a thickness of 10 nm. Next, PYD2Cz and compound 3 were co-deposited from different deposition 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 mass%. Next, ET1 was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-deposited from different deposition sources to form a 20 nm thick layer. The concentrations of Liq and SF3-TRZ in this layer were 30 mass% and 70 mass%, respectively. Furthermore, Liq was formed to a thickness of 2 nm, and then aluminum (Al) was deposited to a thickness of 100 nm to form the cathode, creating an organic electroluminescent device. [ka] [Industrial applicability]

[0126] Compounds represented by general formula (1) exhibit good luminescence performance. Therefore, using compounds represented by general formula (1) can provide excellent organic light-emitting devices. Accordingly, the present invention has high industrial applicability.

Claims

1. A compound represented by the following general formula (1): 【Chemistry 1】 In the general formula (1), A represents a cyanopyridyl group which may be substituted with a phenyl group or a naphthyl group, and a hydrogen atom of the cyanopyridyl group may be substituted with a deuterium atom. 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 two of R each independently represent 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, and a substituted or unsubstituted benzothieno-fused carbazol-9-yl group).

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

3. R ２ The compound according to claim 1 or 2, wherein is an acceptor group.

4. R ３ The compound according to claim 1 or 2, wherein is an acceptor group.

5. The compound according to any one of claims 1 to 4, wherein the acceptor group is a group having the same structure as A.

6. The compound according to any one of claims 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 ２ and R ５ The compound according to any one of claims 1 to 6, wherein each independently is a donor group.

8. The compound according to any one of claims 1 to 7, wherein the donor group is a substituted or unsubstituted diarylamino group (wherein two aryl groups constituting the diarylamino group may be bonded to each other).

9. The compound according to any one of claims 1 to 8, which has a symmetrical structure.

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

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

12. A membrane comprising a compound according to any one of claims 1 to 9.

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

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

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

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

17. 16. The organic light-emitting device of claim 15, wherein the device has a layer that includes the compound, the layer also including a light-emitting material that has a different structure than the compound.

18. The organic light-emitting device according to any one of claims 15 to 17, wherein the amount of light emitted from the compound is the largest among materials contained in the device.

19. The organic light-emitting device of claim 17 , wherein the amount of light emitted from the light-emitting material is greater than the amount of light emitted from the compound.

20. The organic light-emitting device according to any one of claims 14 to 19, which is an organic electroluminescence device.

21. The organic light-emitting device according to any one of claims 14 to 20, which emits delayed fluorescence.

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