Compounds, light-emitting materials, and light-emitting devices

Abstract

To provide an organic light-emitting element excellent in light-emitting properties.SOLUTION: Compounds of the general formula in the figure are used for the organic light-emitting element. In the formula, A represents an acceptor group having a nitrogen-containing aromatic heterocyclic ring; and R1 to R5 are such that one or more thereof represent cyano groups or A, one or more thereof represent donor groups, one or more thereof represent alkyl groups or silyl groups, and the rest thereof represent hydrogen atoms or deuterium atoms.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 these are many compounds in which cyanobenzene is substituted with a donor group and an acceptor group. For example, compounds in which cyanobenzene is substituted with a fused carbazole-9-yl group, which is a donor group, and a diphenyltriazinyl group, which is an acceptor group, have been proposed, and one example is a compound with the following structure (see Patent Document 1).

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

[0006] [Patent Document 1] WO2021 / 046523A1 [Overview of the project] [Problems that the invention aims to solve]

[0007] Even among materials that emit delayed fluorescence, those with extremely good properties and no practical challenges have yet been provided. Therefore, it would be even more useful if a delayed fluorescence material with even better luminescence properties than the delayed fluorescence material proposed in, for example, Patent Document 1 could be provided. In particular, it would be useful to develop a delayed fluorescence material that maintains high luminescence efficiency while having a short delayed fluorescence lifetime and good chromaticity. 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 useful luminescent materials.

[0008] 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]

[0009] As a result of diligent research to achieve the above objectives, the inventors have found that cyanobenzene 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.

[0010] [1] A compound represented by the following general formula (1).

Chemical

Chemical

[10] R 1 ~R 5 A compound according to any one of [1] to [6], wherein at least one of the alkyl groups may be substituted with a deuterium atom.

[11] R 1 A compound described in any one of [1] to

[10] , wherein the compound is a hydrogen atom.

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

[11] .

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

[11] .

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

[11] .

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

[11] .

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

[11] .

[17] The organic light-emitting element according to

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

[18] The organic light-emitting element according to

[17] , 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.

[19] The organic light-emitting element according to

[17] , 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.

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

[17] to

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

[21] The organic light-emitting device according to

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

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

[16] to

[21] .

[23] An organic light-emitting element according to any one of

[16] to

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

[0011] The compounds of the present invention are useful as luminescent materials. Furthermore, some of the compounds of the present invention exhibit good luminescence properties. Some of the compounds of the present invention maintain high luminescence efficiency while exhibiting good chromaticity and a short delayed fluorescence lifetime. [Modes for carrying out the invention]

[0012] 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 ( 2It can be substituted with H (deuterium D). In the chemical structural formulas of this specification, hydrogen atoms are represented as H or their representation is omitted. For example, when the representation of an atom bonded to a carbon atom constituting the ring skeleton of a benzene ring is omitted, it is assumed that H is bonded to the carbon atom constituting the ring skeleton where the representation is omitted. In the chemical structural formulas of this specification, deuterium atoms are represented as D. In this application, "luminescence properties" refers to properties related to luminescence, such as luminescence efficiency, driving voltage, delayed fluorescence lifetime (τ2), and device lifetime (LT50). The compounds of the present invention have excellent luminescence properties at least one of the above.

[0013] [Compounds represented by general formula (1)] [ka]

[0014] In general formula (1), A represents an acceptor group having an aromatic heterocycle containing a nitrogen atom as a constituent atom of the ring skeleton. The number of constituent atoms in the ring skeleton of an aromatic heterocycle is preferably 5 to 7, more preferably 5 or 6, and most preferably 6. The atoms constituting the ring skeleton of an aromatic heterocycle include nitrogen atoms. Preferably, the atoms constituting the ring skeleton of an aromatic heterocycle consist of carbon atoms and nitrogen atoms. Examples of aromatic heterocycles include pyridine rings, pyrimidine rings, pyrazine rings, N-aryl-substituted imidazole rings, N-aryl-substituted pyrrole rings, and N-aryl-substituted azepine rings, and for example, a pyridine ring or a pyrimidine ring may be selected. The group represented by A only needs to have an aromatic heterocyclic ring. Therefore, it may be a group bonded via one of the ring skeleton constituting atoms (particularly a ring skeleton constituting carbon atom) of the aromatic heterocyclic ring, or may be a group in which the aromatic heterocyclic ring is bonded via a linking group. Examples of such a linking group include a substituted or unsubstituted arylene group, a substituted or unsubstituted conjugated alkenylene group, and a substituted or unsubstituted conjugated alkynylene group. The arylene group is preferably a phenylene group or a group formed by linking two phenylene groups. The conjugated alkenylene group has a conjugated linking chain, and is preferably, for example, an ethenylene group or a 1,4-butadienylene group. The conjugated alkynylene group has a conjugated linking chain, and is preferably, for example, an ethynylene group.

[0015] The group represented by A is an acceptor group. The acceptor group as referred to herein can be selected from groups having a positive Hammett σp value. The Hammett σp value was proposed by L.P. Hammett, and quantifies the influence of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, the following formula holds between the substituent and the reaction rate constant or equilibrium constant in a para-substituted benzene derivative: log(k / k0) = ρσp or log(K / K0) = ρσp which is the constant (σp) specific to the substituent in the above formula. In the above formula, k0 is the rate constant of an unsubstituted benzene derivative, k is the rate constant of a benzene derivative substituted with the substituent, K0 is the equilibrium constant of an unsubstituted benzene derivative, K is the equilibrium constant of a benzene derivative substituted with the substituent, and ρ represents a reaction constant determined depending on the type and conditions of the reaction. For the description of "Hammett σp value" and the numerical values of each substituent in the present invention, reference can be made to the description related to σp values in Hansch, C. et. al., Chem. Rev., 91, 165-195 (1991). A is preferably such that σp is 0.3 or greater, more preferably 0.5 or greater, and may be selected from a range of 0.7 or greater, a range of 0.9 or greater, or a range of 1.1 or greater. A preferably has a structure represented by the following general formula (2). [ka]

[0016] X in general formula (2) 1 ~X 3 Each of these independently represents N or C(R). However, X 1 ~X 3 At least one of them is N. R represents a hydrogen atom or a substituent (substituents include deuterium atoms). The substituent here may be selected from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E. In a preferred embodiment of the present invention, X 1 ~X 3 is N. In one aspect of the present invention, X 1 and X 3 N is X 2 C(R) is C(R). In one aspect of the present invention, X 1 and X 2 N is X 3 C(R) is C(R). In one aspect of the present invention, X 1 N is X 2 and X 3 C(R) is C(R). In one aspect of the present invention, X 2 N is X 1 and X 3 is C(R). In one aspect of the present invention, R is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R is an alkyl group which may be substituted with a deuterium atom. In one aspect of the present invention, R is an aryl group which may be substituted with a deuterium atom, an alkyl group or an aryl group. In one aspect of the present invention, X 2 C(R) is Ar 2 It combines with other elements to form an aromatic ring.

[0017] Ar in general formula (2) 1 Ar represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 2 X represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. 2 or X 3 When C(R) is present, it combines with R to form an aromatic ring. 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. A "heteroaryl 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 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 a heteroaryl group is preferably 4 to 40, more preferably 5 to 20, and can be selected within the range of 5 to 14 or within the range of 5 to 10. In one preferred embodiment of the present invention, Ar1 and Ar 2 is a substituted or unsubstituted aryl group, preferably a substituted or unsubstituted phenyl group, and more preferably a phenyl group which may be substituted with one atom or group or a combination of two or more groups selected from the group consisting of a deuterium atom and a phenyl group. In one preferred embodiment of the present invention, it is an unsubstituted phenyl group. In one embodiment of the present invention, Ar 1 and Ar 2 is a substituted or unsubstituted heteroaryl group. In a preferred embodiment of the present invention, Ar 1 and Ar 2 They are identical.

[0018] In the following, Ar 1 and Ar 2 The following are specific examples of substituted or unsubstituted aryl groups that can be adopted. However, Ar 1 and Ar 2 The substituted or unsubstituted aryl groups that can be formed are not limited by these specific examples. Note that in the following examples, methyl groups are omitted from the notation. Therefore, for example, Ar4 is substituted with a methyl group, and Ar5 is substituted with an isopropyl group. * indicates the bond position. [ka]

[0019] The following are disclosed, in which all hydrogen atoms in Ar1 to Ar20 are replaced with deuterium atoms, and are referred to as Ar21 to Ar40 in order. The following are disclosed, in which all hydrogen atoms in the phenyl group or alkyl group substituents of Ar4 to Ar20 are replaced with deuterium atoms, and are referred to as Ar41 to Ar57 in order. In one aspect of the present invention, R 1 ~R 5 The substituted or unsubstituted aryl groups that can be adopted are selected from Ar1 to Ar57. In one aspect of the present invention, R 1 ~R 5The substituted or unsubstituted aryl groups that can be adopted are selected from Ar1-Ar3, Ar19-Ar23, Ar39, Ar40, Ar56, and Ar57. In one aspect of the present invention, R 1 ~R 5 The substituted or unsubstituted aryl groups that can be adopted are Ar1 or Ar21. In one aspect of the present invention, R 1 ~R 5 The substituted or unsubstituted aryl groups that can be adopted are selected from Ar1, Ar4-Ar18, Ar21, Ar24-Ar38, and Ar41-Ar55.

[0020] Below, Ar 1 and Ar 2 As specific examples of substituted or unsubstituted heteroaryl groups that can be adopted, Ar58 to Ar62 and Ar63 to Ar67, in which all hydrogen atoms in Ar58 to Ar62 are replaced with deuterium atoms, are shown below. However, Ar 1 and Ar 2 The substituted or unsubstituted heteroaryl groups that can be formed are not limited by these specific examples. In the following examples, * indicates the bond position. [ka]

[0021] In one aspect of the present invention, Ar 1 and Ar 2 Ar is selected from Ar1 to Ar67. In one preferred embodiment of the present invention, Ar 1 and Ar 2 Ar is selected from Ar1 to Ar57. In one aspect of the present invention, Ar 1 and Ar 2 Ar1 to Ar3, Ar19 to Ar23, Ar39, Ar40, Ar56, Ar57 are selected from among Ar1 to Ar3, Ar19 to Ar23, Ar39, Ar40, Ar56, and Ar57. In one aspect of the present invention, Ar 1 and Ar 2 Ar is selected from Ar1, Ar4~Ar18, Ar21, Ar24~Ar38, Ar41~Ar55. In one aspect of the present invention, Ar 1 and Ar 2is selected from Ar1, Ar19, Ar21 and Ar57. In one aspect of the present invention, Ar 1 and Ar 2 are identical. In one aspect of the present invention, Ar 1 and Ar 2 are different. For example, preferred embodiments include an embodiment where both Ar 1 and Ar 2 are Ar1, an embodiment where both Ar 1 and Ar 2 are Ar21, an embodiment where Ar 1 is Ar1 and Ar 2 is Ar19, and an embodiment where Ar 1 is Ar21 and Ar 2 is Ar57.

[0022] Ar in general formula (2) 2 , when X 2 or X 3 is C(R), may bond to said R to form an aromatic ring. In a preferred aspect of the present invention, X 2 is C(R), and Ar 2 bonds to said R to form an aromatic ring. In one aspect of the present invention, X 3 is C(R), and Ar 2 bonds to said R to form an aromatic ring. The formed aromatic ring is preferably a benzene ring. The formed aromatic ring may also be a heteroaromatic ring, and in this case, it preferably contains a nitrogen atom as a ring skeleton constituent atom. Specific examples of heteroaromatic rings include a pyridine ring and a pyrimidine ring. These benzene rings and heteroaromatic rings may be substituted, and the substituents in this case may be selected, for example, from substituent group A, may be selected from substituent group B, may be selected from substituent group C, may be selected from substituent group D, or may be selected from substituent group E. In one aspect of the present invention, the benzene ring or heteroaromatic ring is unsubstituted. Specific examples of structures in which Ar 2 bonds to R to form an aromatic ring are shown below. However, Ar 2The structure in which R is bonded to form an aromatic ring is not limited to these specific examples. In the following examples, * is L 1 This indicates the bond position to the atom. The hydrogen atoms in the structure below may be substituted with substituents (substituents here include deuterium atoms). [ka]

[0023] Below, Ar 2 The following are specific examples of acceptor group A, which includes a structure in which is bonded to R to form an aromatic ring. In the following examples, Ph is a phenyl group, and * indicates the bond position to the benzene ring of general formula (1). [ka]

[0024] L in general formula (2) 1 represents a single bond or a divalent linking group. Examples of divalent linking groups include substituted or unsubstituted arylene groups and substituted or unsubstituted heteroarylene groups. In a preferred embodiment of the present invention, L 1 It is a single bond. In one aspect of the present invention, L 1 L is a substituted or unsubstituted arylene group. In one aspect of the present invention, L 1 This is a substituted or unsubstituted heteroarylene group. The aryl portion constituting the arylene group is as described above. 1 and Ar 2 You can refer to the description and preferred range of the aryl group in the section indicated. Examples of heteroarylene groups include linking groups in which at least one carbon atom of the ring skeleton constituting the arylene group is substituted with a nitrogen atom. In the following, L 1 Let us give some specific examples. However, L which can be used in the present invention 1shall not be construed as limited by these specific examples. In the following specific examples, the indication of methyl groups is omitted. Therefore, for example, L3 to L5 are substituted with methyl groups. * indicates a bonding position. L1 is a single bond.

[0025]

Chemical

[0026] In a preferred embodiment of the present invention, X 1 to X 3 is N, and Ar 1 and Ar 2 is a substituted or unsubstituted aryl group (preferably a substituted or unsubstituted phenyl group, more preferably a phenyl group), and L 1 is a single bond. In one embodiment of the present invention, X 1 to X 3 is N, and Ar 1 and Ar 2 is a substituted or unsubstituted aryl group (preferably a substituted or unsubstituted phenyl group, more preferably a phenyl group), and L 1 is L2. In one embodiment of the present invention, X 1 to X 3 is N, and Ar 1 and Ar 2 is a substituted or unsubstituted aryl group (preferably a substituted or unsubstituted phenyl group, more preferably a phenyl group), and L 1 is L6. In a preferred embodiment of the present invention, X 1 and X 3 is N, X 2 is C(R), Ar 1 is a substituted or unsubstituted aryl group (preferably a substituted or unsubstituted phenyl group, more preferably a phenyl group), Ar 2 is bonded to R to form a substituted or unsubstituted benzene ring, and L 1 is a single bond.

[0027] In general formula (1), R 1 ~R 5 At least one of these represents, independently, a cyano group or a heteroaryl group containing a nitrogen atom as a constituent atom of the ring skeleton. For details on heteroaryl groups containing a nitrogen atom as a constituent atom of the ring skeleton, please refer to the explanation in A above. In one aspect of the present invention, R 1 ~R 5 One or two of these are, each independently, a cyano group or a heteroaryl group containing a nitrogen atom as a ring skeleton constituent atom, preferably R 1 ~R 5 Only one of them is a heteroaryl group containing a nitrogen atom as a cyano group or a ring skeleton constituent atom. In one aspect of the present invention, R 1 Only R is a cyano group. In a preferred embodiment of the present invention, R 4 Only R is a cyano group. In a preferred embodiment of the present invention, R 5 Only R is a cyano group. In one aspect of the present invention, R 1 Only the heteroaryl group containing a nitrogen atom as a ring skeleton constituent atom is R 4 Only heteroaryl groups containing a nitrogen atom as a ring skeleton constituent atom are present. In a preferred embodiment of the present invention, R 5 Only this group contains a nitrogen atom as a constituent atom of the ring skeleton, making it a heteroaryl group.

[0028] In general formula (1), R 1 ~R 5 At least one of these is independently a substituted or unsubstituted alkyl group, or a substituted or unsubstituted silyl group. The alkyl group may be linear, branched, or cyclic, with linear or branched being preferred. 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 group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group, 2-ethylhexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decanyl group, isodecanyl group, cyclopentyl group, cyclohexyl group, and cycloheptyl group. The "silyl group" may or may not be substituted. If substituted, only one substituent may be substituted, two substituents may be substituted, or all three substituents may be substituted. If two or more substituents are substituted, the substituents may be the same or different, but it is preferable that they be the same. It is preferable that the silyl group is either unsubstituted or all three substituents are substituted. If substituted, the substituents are preferably selected from substituent group E. In the following, R 1 ~R 5 Specific examples of substituted or unsubstituted alkyl groups and substituted or unsubstituted silyl groups that can be adopted are given below. However, the alkyl groups and silyl groups that can be used in the present invention are not limited by these specific examples. In the following examples, the methyl group is omitted from the notation, and M1 represents a methyl group. * indicates the bond position.

[0029] [ka]

[0030] The following are disclosed as M8 to M14, in which all hydrogen atoms in M1 to M7 are replaced with deuterium atoms. In one aspect of the present invention, R1 ~R 5 The substituted or unsubstituted alkyl groups, or substituted or unsubstituted silyl groups that can be adopted are selected from M1 to M14. In one aspect of the present invention, they are selected from M1 to M5 and M8 to M12. In one aspect of the present invention, they are selected from M8 to M14. In one aspect of the present invention, they are selected from M1 to M4 and M8 to M11. In one aspect of the present invention, they are selected from M6, M7, M13, and M14. In one aspect of the present invention, they are selected from M5 and M12.

[0031] In general formula (1), R 1 ~R 5 At least one of them is a donor group. The donor group referred to here can be selected from groups with a negative Hammett σp value. Preferably, the σp value is -0.3 or less, more preferably -0.5 or less, and for example, it may be selected from the range of -0.7 or less, the range of -0.9 or less, or the range of -1.1 or less.

[0032] R 1 ~R 4 The donor group that can be adopted is preferably a group represented by the following general formula (a). [ka]

[0033] In general formula (a), Z 1 CR 14 Or it represents N, Z 2 CR 15 Or it represents N, Z 3 CR 16 Or it represents N, Z 4 CR 17 Or it represents N. 5 represents C or N, and Ar 5 R represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted complex aromatic ring. 14 and R 15 , R 15 and R 16 , R16 and R 17 They may be joined together to form a ring structure.

[0034] Z 1 ~Z 4 Of these, the number of N is preferably 0 to 3, and more preferably 0 to 2. In one aspect of the present invention, Z 1 ~Z 4 Of these, the number of those that are N is 1. In one aspect of the present invention, Z 1 ~Z 4 The number of items that are N is 0. R 14 ~R 17 Each of these independently represents a hydrogen atom or a substituent (substituents include deuterium atoms). The substituent may be selected from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E. 14 ~R 17 When two or more of these represent substituents, those two or more substituents may be the same or different. 14 ~R 17 Preferably, 0 to 2 of these are substituents; for example, 1 may be a substituent, or 0 may be substituents. R 14 and R 15 , R 15 and R 16 , R 16 and R 17These elements may be bonded to each other to form a cyclic structure. The cyclic structure may be an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, or an aliphatic heterocycle, or a ring formed by the fusion of these elements. Preferably, it is an aromatic ring or a heteroaromatic ring. As an aromatic ring, a substituted or unsubstituted benzene ring can be given. The benzene ring may be further fused with other benzene rings, or with a heterocycle such as a pyridine ring. A heteroaromatic ring means an aromatic ring that contains heteroatoms as constituent atoms of the ring skeleton, and is preferably a 5- to 7-membered ring; for example, a 5-membered ring or a 6-membered ring can be used. In one embodiment of the present invention, a furan ring, a thiophene ring, or a pyrrole ring can be used as the heteroaromatic ring. In a preferred embodiment of the present invention, the cyclic structure is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, or a pyrrole ring of substituted or unsubstituted indole. The benzofuran, benzothiophene, and indole referred to herein may be unsubstituted, substituted with substituents selected from substituent group A, substituents selected from substituent group B, substituents selected from substituent group C, substituents selected from substituent group D, or substituents selected from substituent group E. It is preferable that a substituted or unsubstituted aryl group is bonded to the nitrogen atom constituting the pyrrole ring of indole, and examples of such substituents include those selected from any of substituent groups A to E. The cyclic structure may be a substituted or unsubstituted cyclopentadiene ring. In one aspect of the present invention, R 14 and R 15 , R 15 and R 16 , R 16 and R 17 One pair within is joined to each other to form a ring structure. In one aspect of the present invention, R 14 and R 15 , R 15 and R 16 , R 16 and R 17 None of them are bonded to each other to form a ring structure.

[0035] In general formula (a), Z 5 represents C or N, and Ar 5 represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. In one aspect of the present invention, Z 5 is C, and Ar 5 is a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring. In one aspect of the present invention, Z 5 is N, and Ar 5 It is a substituted or unsubstituted heteroaromatic ring. Ar 5 One possible aromatic ring that can be formed is a benzene ring. The benzene ring may have other benzene rings fused to it, or it may have a heterocycle such as a pyridine ring fused to it. 5 The heteroaromatic ring that can be adopted is preferably a 5- to 7-membered ring, for example, a 5-membered ring or a 6-membered ring can be adopted. In one aspect of the present invention, a furan ring, thiophene ring, pyrrole ring, imidazole ring, pyridine ring, pyridazine ring, pyrimidine ring, or pyrazine ring can be adopted as the heteroaromatic ring. In one aspect of the present invention, Z 5 C is C, and the heteroaromatic ring is a furan ring of substituted or unsubstituted benzofuran, a thiophene ring of substituted or unsubstituted benzothiophene, a pyridine ring of substituted or unsubstituted quinoline, or a pyridine ring of substituted or unsubstituted isoquinoline. In one aspect of the present invention, Z 5 The molecule is N, and the heteroaromatic ring is a pyrrole ring of indole that is substituted or unsubstituted, or an imidazole ring of benzimidazole that is substituted or unsubstituted. Here, benzofuran, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole may be unsubstituted, or they may be substituted with substituents selected from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E.

[0036] Z in general formula (a) 5When is C, it is preferable that it is a group represented by the following general formula (b). [ka]

[0037] In general formula (b), Z 1 CR 14 Or it represents N, Z 2 CR 15 Or it represents N, Z 3 CR 16 Or it represents N, Z 4 CR 17 Or it represents N, Z 6 CR 18 Or it represents N, Z 7 CR 19 Or it represents N, Z 8 CR 20 Or it represents N, Z 9 CR 21 Or it represents N. 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 18 and R 19 , R 19 and R 20 , R 20 and R 21 They may be joined together to form a ring structure. Z in general formula (b) 1 ~Z 4 , R 14 ~R 17 For this, refer to the corresponding explanation in general formula (a). Z in general formula (b) 6 ~Z 9 , R 18 ~R 21 This is Z of general formula (a). 1 ~Z 4 , R 14 ~R 17 These correspond in order, and for these contents, Z of general formula (a) 1 ~Z 4 , R 14 ~R 17You can refer to the explanation. In one aspect of the present invention, Z 1 ~Z 4 , Z 6 ~Z 9 The number of N is preferably 0 to 2, and preferably 0 or 1. In one aspect of the present invention, Z 1 ~Z 4 , Z 6 ~Z 9 Of these, the number of those that are N is 1. In a preferred embodiment of the present invention, Z 1 ~Z 4 , Z 6 ~Z 9 The number of Ns among them is 0. When it is 0, it represents a substituted or unsubstituted carbazole-9-yl group. The carbazole-9-yl group may be unsubstituted, or it may be substituted with a substituent 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, D is a carbazole-9-yl group substituted with a group containing at least one substituted or unsubstituted aryl group, for example, a carbazole-9-yl group substituted with at least one substituted or unsubstituted aryl group. In one embodiment of the present invention, at least one of the 2-position and the 7-position is a substituted or unsubstituted aryl group. In one embodiment of the present invention, at least one of the 3-position and the 6-position is a substituted or unsubstituted aryl group. The aryl group referred to herein may be unsubstituted, or it may be substituted with a substituent selected from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E.

[0038] R 1 ~R 4The donor group that can be adopted is a substituted or unsubstituted indole-1-yl group, in which the indole ring constituting the indole-1-yl group is fused with another ring, thereby forming a fused ring with four or more rings. Hereafter in this specification, a group that satisfies this condition will be referred to as a "fused indole-1-yl group".

[0039] The fused indole-1-yl group may be polycyclic with one ring fused to the benzene or pyrrole ring constituting the indole-1-yl group, or it may be polycyclic or monocyclic with two or more rings. For example, when two rings are fused, it is preferable that one is fused to the benzene ring and the other to the pyrrole ring. The two fused rings may be the same or different. The fusion of rings to the indole ring may form a fused ring with four or more, five or more, or six or more rings, and it is preferable to form a fused ring with five or more rings. For example, compounds forming a fused ring with four rings, compounds forming a fused ring with five rings, compounds forming a fused ring with six rings, and compounds forming a fused ring with eight rings may be used. The ring may be fused only to the 2,3 position (b), only to the 4,5 position (e), only to the 5,6 position (f), only to the 6,7 position (g), or to both the 4,5 position (e) and the 6,7 position (g). Alternatively, it may be fused to one of the 4,5 position (e), 5,6 position (f), or 6,7 position (g) and to the 2,3 position (b) (see the formula below, where * indicates a bond position). [ka]

[0040] The ring that directly condenses with the benzene ring or pyrrole ring constituting the indole-1-yl group (if the condensing ring is polycyclic, this refers only to the ring that directly condenses among the rings constituting that polycyclic ring) may be an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, or an aliphatic heterocycle. Preferably, one or more rings selected from the group consisting of benzene rings and aromatic heterocycles are directly condensed. The heterocyclic ring referred to here is a ring containing a heteroatom. The heteroatom is preferably selected from oxygen, sulfur, nitrogen, and silicon atoms, and more preferably selected from oxygen, sulfur, and nitrogen atoms. In one preferred embodiment, the heteroatom is an oxygen atom. In another preferred embodiment, the heteroatom is a sulfur atom. In yet another preferred embodiment, the heteroatom is a nitrogen atom. The number of heteroatoms included as ring skeleton constituent atoms of the heterocyclic ring is one or more, preferably 1 to 3, and more preferably 1 or 2. In one preferred embodiment, the number of heteroatoms is one. When the number of heteroatoms is two or more, they are preferably of the same type, but they may be composed of different types of heteroatoms. For example, two or more heteroatoms may all be nitrogen atoms. The ring skeleton constituent atoms other than the heteroatoms are carbon atoms. The number of ring skeleton constituent atoms constituting the heterocyclic ring directly fused to the benzene ring constituting the indole-1-yl group is preferably 4 to 8, more preferably 5 to 7, and even more preferably 5 or 6. In one preferred embodiment, the number of constituent atoms in the ring skeleton constituting the heterocycle is 5. Preferably, the heterocycle has two or more conjugated double bonds, and preferably, the conjugated system of the indole ring is extended by the condensation of the heterocycle (i.e., it is preferably aromatic). Preferred examples of heterocycles include furan rings, thiophene rings, and pyrrole rings. The rings directly fused to the benzene or pyrrole rings constituting the indole-1-yl group may have other rings fused to them as well. Furthermore, the fused rings may be monorings or fused rings. Examples of fused rings include aromatic hydrocarbon rings, aromatic heterocyclic rings, aliphatic hydrocarbon rings, and aliphatic heterocyclic rings. In a preferred embodiment of the present invention, at least one heterocycle is directly fused to the benzene ring or pyrrole ring constituting the indole-1-yl group. In a preferred embodiment of the present invention, the fused ring constituting the fused indole-1-yl group contains two or more heterocycles. For example, it may contain two heterocycles or three heterocycles.

[0041] Examples of aromatic hydrocarbon rings in this specification include benzene rings. Examples of aromatic heterocycles include furan rings, thiophene rings, pyrrole rings, pyridine rings, pyridazine rings, pyrimidine rings, pyrazine rings, triazine rings, pyrrole rings, pyrazole rings, and imidazole rings. Examples of aliphatic hydrocarbon rings include cyclopentane rings, cyclohexane rings, and cycloheptane rings. Examples of aliphatic heterocycles include piperidine rings, pyrrolidine rings, and imidazoline rings. Specific examples of condensed rings include naphthalene rings, anthracene rings, phenanthrene rings, pyran rings, tetracene rings, indole rings, isoindole rings, benzimidazole rings, benzotriazole rings, quinoline rings, isoquinoline rings, quinazoline rings, quinoxaline rings, and sinnoline rings.

[0042] In a preferred embodiment of the present invention, the fused indole-1-yl group is a benzofuran-fused indole-1-yl group, a benzothiophene-fused indole-1-yl group, an indole-fused indole-1-yl group, or an indene-fused indole-1-yl group. Preferably, it is a group represented by the following general formula (3). [ka]

[0043] In general formula (3), X is O, S, N(R 9 ) or C(R 10 )(R 11 ) represents. Preferably O, S or N(R 9) and more preferably O or S. In one preferred embodiment of the present invention, X is O. In one preferred embodiment of the present invention, X is S. Note that in general formula (3), (R 8 ) n8 The benzene ring in the upper right to which it is bonded and (R 7 ) n7 The central benzene ring to which is bonded is connected by an X-mediated bond and a single bond, but the relative positions of these two bonds are not restricted. In the general formula (3) above, the X-mediated bond is written above and the single bond is written below, but general formula (3) also includes structures in which the X-mediated bond is located below and the single bond is located above. In general formula (3), n6 and n8 each independently represent an integer from 0 to 4, preferably from 0 to 2, and more preferably 0 or 1. n7 represents an integer from 0 to 2, preferably 0 or 1. n6 + n7 + n8 is an integer from 0 to 10, for example from 0 to 4, for example from 0 to 2. In one aspect of the present invention, n6 is from 1 to 4. In one aspect of the present invention, n7 is 1 or 2. In one aspect of the present invention, n8 is from 1 to 4. In general formula (3), R 6 ~R 8 Each of these independently represents a substituent (substituents include deuterium atoms). A substituent may be selected from substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E. In general formula (3), R is bonded to adjacent ring skeleton constituent carbon atoms. 6 R is bonded to adjacent carbon atoms in the ring skeleton. 7 R is bonded to adjacent carbon atoms in the ring skeleton. 8 These elements may bond to each other to form a cyclic structure. The cyclic structure formed can be described by referring to the general formula (a) above. In one aspect of the present invention, R is bonded to adjacent carbon atoms constituting the ring skeleton. 6They are bonded to each other to form a cyclic structure, preferably a benzofloxacin structure or a benzothieno structure. In one aspect of the present invention, R is bonded to adjacent carbon atoms of the ring skeleton. 8 They are bonded to each other to form a cyclic structure, preferably a benzofloxacin structure or a benzothieno structure. In one aspect of the present invention, R 6 Allies, R 7 Allies, R 8 They are not bonded to each other to form a ring structure. 6 and R 7 , R 7 and R 8 They do not combine with each other to form a ring structure. In general formula (3), * represents the bond position.

[0044] In the following, R in general formula (1) 1 ~R 5 Specific examples of donor groups that can be used are shown below. However, the donor groups that can be used in the present invention 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, D2 has one methyl group. [ka] JPEG0007923516000017.jpg253169JPEG0007923516000018.jpg205170JPEG0007923516000019.jpg20417 0JPEG0007923516000020.jpg225170JPEG0007923516000021.jpg219170JPEG0007923516000022.jpg22817 0JPEG0007923516000023.jpg221170JPEG0007923516000024.jpg219170JPEG0007923516000025.jpg23516 0JPEG0007923516000026.jpg206167JPEG0007923516000027.jpg212169JPEG0007923516000028.jpg23415 4JPEG0007923516000029.jpg226169JPEG0007923516000030.jpg188170JPEG0007923516000031.jpg24216 8JPEG0007923516000032.jpg232166JPEG0007923516000033.jpg212170JPEG0007923516000034.jpg22017 0JPEG0007923516000035.jpg245170JPEG0007923516000036.jpg206170JPEG0007923516000037.jpg24217 0JPEG0007923516000038.jpg242168JPEG0007923516000039.jpg209170JPEG0007923516000040.jpg45170

[0045] The above D1 to D420 are disclosed as D421 to D840, in which all hydrogen atoms present are replaced with deuterium atoms. The above D2 to D6, D19 to D42, D49 to D78, D100, D101, D106, D107, D112, D113, D118, D119, D153 to D156, D159 to D323, and D412 to D419 are disclosed as D841 to D1084, in which all hydrogen atoms present in the phenyl groups or alkyl groups that are substituents are replaced with deuterium atoms. In one aspect of the present invention, R of general formula (1) 1 ~R 5 The donor groups that can be adopted are selected from the group consisting of D1 to D1084. In one preferred embodiment of the present invention, R 1 ~R 5 The donor groups that can be adopted are selected from the groups consisting of D13-D78, D84-D119, and D150-D420.

[0046] R in general formula (1) 1 ~R 5 Of these, those that are neither acceptor groups having an aromatic heterocycle containing a nitrogen atom as a constituent atom of the ring skeleton, nor cyano groups, nor substituted or unsubstituted alkyl groups, nor substituted or unsubstituted silyl groups, nor donor groups (the remaining R 1 ~R 5 ) are each independently a hydrogen atom or a deuterium atom. The remaining R 1 ~R 5 The number is 0 to 2, for example 0, for example 1, for example 2. In one aspect of the present invention, the remaining R 1 ~R 5 All of them are hydrogen atoms. In one aspect of the present invention, the remaining R 1 ~R 5 All of them are deuterium atoms. In one aspect of the present invention, at least R 1 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, at least R 2 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, at least R 3 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, at least R 4 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, at least R 5 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 1 and R 2 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 1 and R 3 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 1 and R 4 is a hydrogen atom or a deuterium atom. In one aspect of the present invention, R 1 ~R5 It cannot be a substituted or unsubstituted aryl group.

[0047] In one preferred embodiment of the present invention, A is a group represented by general formula (2), and R 2 ~R 4 At least one of them is a donor group, R 2 ~R 4 At least one of them is a substituted or unsubstituted alkyl group, R 2 ~R 4 The remainder and R 1 is a hydrogen atom or a deuterium atom, R 5 This is a cyano group. In one preferred embodiment of the present invention, A is a group represented by general formula (2), and R 3 and R 4 At least one of them is a donor group, R 2 R is a substituted or unsubstituted alkyl group, 2 ~R 4 The remainder and R 1 is a hydrogen atom or a deuterium atom, R 5 This is a cyano group. In one preferred embodiment of the present invention, A is a group represented by general formula (2), and R 2 and R 4 At least one of them is a donor group, R 3 R is a substituted or unsubstituted alkyl group, 2 ~R 4 The remainder and R 1 is a hydrogen atom or a deuterium atom, R 5 This is a cyano group. In one preferred embodiment of the present invention, A is a group represented by general formula (2), and R 2 and R 3 At least one of them is a donor group, R 4 R is a substituted or unsubstituted alkyl group, 2 ~R 4 The remainder and R 1 is a hydrogen atom or a deuterium atom, R 5 This is a cyano group.

[0048] 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. Furthermore, 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. Moreover, the compound represented by general formula (1) may be a compound containing a deuterium atom.

[0049] In this specification, "substituent group A" refers to deuterium atoms, hydroxyl groups, halogen atoms (e.g., fluorine atoms, chlorine atoms, bromine atoms, iodine atoms), alkyl groups (e.g., C1-40), alkoxy groups (e.g., C1-40), alkylthio groups (e.g., C1-40), aryl groups (e.g., C6-30), aryloxy groups (e.g., C6-30), arylthio groups (e.g., C6-30), heteroaryl groups (e.g., 5-30 atoms in the ring skeleton), heteroaryloxy groups (e.g., 5-30 atoms in the ring skeleton), This refers to a group consisting of one atom or group, or a combination of two or more groups, selected from the group comprising heteroarylthio groups (e.g., 5-30 atoms in the ring skeleton), 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), 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 atom or group, or a combination of two or more groups, selected from the group consisting of deuterium atoms, 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., 5 to 30 atoms in the ring skeleton), heteroaryl 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 atom or group, or a combination of two or more atoms, selected from the group consisting of deuterium atoms, 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 atom or group, or a combination of two or more, selected from the group consisting of deuterium atoms, 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 atom or group, or a combination of two or more atoms or groups, selected from the group consisting of deuterium atoms, alkyl groups (e.g., having 1 to 20 carbon atoms), and aryl groups (e.g., having 6 to 22 carbon atoms). Where a substituent is described as "substituted or unsubstituted" or "may be substituted" in this specification, it may be selected from, for example, substituent group A, substituent group B, substituent group C, substituent group D, or substituent group E.

[0050] Tables 1 to 5 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 specific examples.

[0051] Tables 1 and 2 show the R of general formula (1a).1 ~R 4 The structure of each compound is identified by identifying the R of each compound. Table 1 shows the R of compounds 1 to 150. 1 ~R 4 The structure of each compound is identified by defining each of these. For example, for compound 1, the R of general formula (1a) 1 and R 4 H is R 2 D1 is R 3 It has a structure in which M1 is present. Table 2 shows the R values ​​of multiple compounds in each row. 1 ~R 4 By displaying them together, the structures of compounds 1 to 15176 are shown. For example, in the row for compounds 1 to 1084 in Table 2, R 1 and R 4 H is R 3 It is fixed to M1, R 2 Compounds that are D1 to D1084 are designated as Compounds 1 to 1084 in order. Therefore, in the row for Compounds 1 to 1084 in Table 2, Compounds 1 to 150 are a collective representation of Compounds 1 to 150 identified in Table 1. Similarly, in the row for Compounds 1085 to 2168 in Table 2, R 1 and R 4 H is R 3 It is fixed to M2, R 2 Compounds D1-1084 are designated as compounds 1085-2168, respectively. The structures of compounds 2169-15176 in Table 2 were identified in the same manner. [ka] [Table 1] [Table 2]

[0052] Table 3 shows the R values ​​of multiple compounds in each row. 1 ~R 4By further grouping and displaying them, the structures of compounds 1 to 455280 are shown. Compounds 1 to 455280 in Table 3 are R 1 ~R 4 One or two of them are one of D1 to D1084, and R 1 ~R 4 The structure is identified in which 1 to 3 of the elements are one of M1 to M14. In each row of Table 2, first M1 to M14 are fixed to one element, and then the compounds are identified by sequentially changing D1 to D1084. After that, M1 to M14 are fixed to the next element, and then the compounds are identified by sequentially changing D1 to D1084. In other words, the row for compounds 1 to 15176 in Table 3 is a collective display of compounds 1 to 15176 identified in Table 2. If it is the row for compounds 15177 to 30352 in Table 3, then R 1 and R 3 H is R 4 It is fixed to M1, R 2 Compounds 15177 to 16260 are those where D1 to D1084 are, in order, R 1 and R 3 H is R 4 It is fixed to M2, R 1 Compounds 16261 to 17344 are those where D1 to D1084, and R 1 and R 3 H is R 4 It is fixed to M3, R 1 Compounds 17345 to 18428 are those where D1 to D1084 are, and R 1 and R 3 H is R 4 It is fixed to M14, R 1 Compounds 29269 to 30352 are those with D1 to D1084, respectively. Compounds 30353 to 455280 have also been identified using the same procedure. In the "Note" column of Table 3, R 1 ~R 4 It identifies the items that are the same within that group. [Table 3]

[0053] Up to this point, A in general formula (1) is equivalent to Ar in general formula (2). 1 and Ar 2 The group is a phenyl group (Ar1), X 1 ~X 3 N is L 1 Compounds with a single bond were identified as compounds 1-455280. Table 4 shows the Ar for each of compounds 1 to 455280. 1 and Ar 2 The compounds obtained by substituting as shown in Table 4 are displayed sequentially in a table format. Table 4 also shows compounds 1 to 455280 to make the correspondence easier to understand. For example, compound 1(1) is the same as compound 1's Ar 2 This shows a compound having a structure in which Ar1 is replaced with Ar2. Also, compound 2(1) is the Ar of compound 2 2 This shows a compound having a structure in which Ar1 is replaced with Ar2. Compound 455280(1) is the Ar of compound 455280 2 This shows compounds having a structure in which Ar1 is replaced with Ar2. Compounds 1(2) to 455280(2) and subsequent compounds in Table 4 were identified in the same manner. Table 5 sequentially displays, in table format, the compounds obtained by substituting A as shown in Table 5 for each of the compounds 1 to 455280. For example, compound 1 (133) represents a compound having a structure in which the 3,5-diphenyl-2,4,6-triazinyl group, which is A in compound 1, is substituted with A1. Compound 2 (133) represents a compound having a structure in which the 3,5-diphenyl-2,4,6-triazinyl group, which is A in compound 2, is substituted with A1. Subsequent compounds in Table 5 were identified in the same manner. [Table 4] JPEG0007923516000046.jpg177170 [Table 5]

[0054] Using Tables 1-5, let R in general formula (1) 1 ~R 5Specific examples of compounds in which one or two are hydrogen atoms are given as compounds 1-455280(148). 1 ~R 5 Compounds 1d to 455280d(148) are further examples, in which each hydrogen atom in compound 1 is replaced with a deuterium atom. Furthermore, compounds 1D to 455280D(148) are further examples, in which all hydrogen atoms in compound 1 to 455280(148) are replaced with deuterium atoms. All of these exemplary compounds are disclosed individually in this specification.

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

[0056] 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.

[0057] 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.

[0058] 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]

[0059] 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 11 L 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 104Each 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.

[0060] As a concrete example of a repeating unit structure, we can cite the structure represented by the following formula. [ka]

[0061] 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]

[0062] 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.

[0063] 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, green, yellow, orange, and red regions of the visible spectrum (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 600 nm to about 700 nm) or the near-infrared region when excited by thermal or electronic means. In some embodiments of this disclosure, a compound represented by general formula (1) can emit light in the blue region of the visible spectrum (e.g., about 400 nm to about 490 nm, about 475 nm) when excited by thermal or electronic means. In 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).

[0064] 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 ST value 4. Quantum yield above a specific value 5. HOMO levels 6. LUMO levels In one embodiment, the difference (ΔE) between the lowest singlet excited state and the lowest triplet excited state at 77K is ST ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 eV, or less than about 0.1 eV. In one embodiment, ΔE ST The values ​​are less than approximately 0.09 eV, less than approximately 0.08 eV, less than approximately 0.07 eV, less than approximately 0.06 eV, less than approximately 0.05 eV, less than approximately 0.04 eV, less than approximately 0.03 eV, less than approximately 0.02 eV, or less than approximately 0.01 eV. In one embodiment, the compound represented by general formula (1) exhibits a quantum yield of more than 25%, for example, 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 higher.

[0065] [Method for synthesizing compounds represented by general formula (1)] The compounds represented by general formula (1) include novel compounds. Compounds represented by general formula (1) can be synthesized by combining known reactions. For example, R of general formula (1) 1 ~R 5 By synthesizing a compound in which the donor group is a halogen atom and reacting it with DH, the compound of general formula (1) can be synthesized. For details of the reaction conditions, please refer to the synthesis examples described later.

[0066] [Constructions using compounds 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).

[0067] [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 one embodiment, a film containing the compounds of the present invention can be formed by a dry process. In another embodiment, a vacuum deposition method can be used as the dry process, but is not limited to this. When a vacuum deposition method is used, the compounds constituting the film may be co-deposited from individual deposition sources, or from a single deposition source containing a mixture of compounds. When a single deposition source is used, a mixed powder of compound powders may be used, a compressed molded body obtained by compressing the mixed powder may be used, or a mixture obtained by heating, melting, and cooling each compound may be used. In one embodiment, by performing co-deposition under conditions where the deposition rates (weight loss rates) of multiple compounds contained in a single deposition source are the same or nearly the same, a film with a composition ratio corresponding to the composition ratio of multiple compounds contained in the deposition source can be formed. By mixing multiple compounds in the same composition ratio as the composition ratio of the formed film to create a deposition source, a film with a desired composition ratio can be easily formed. In one embodiment, the temperature at which each co-deposited compound has the same weight loss rate can be identified, and that temperature can be adopted as the temperature during co-deposition.

[0068] [Examples of the use of compounds represented by general formula (1)] Compounds represented by general formula (1) are useful as materials for organic light-emitting devices. They are particularly preferred for use in organic light-emitting diodes and the like. Organic light-emitting diodes: 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.

[0069] 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.

[0070] 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).

[0071] [ka] JPEG0007923516000053.jpg219166JPEG0007923516000054.jpg255169

[0072] 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).

[0073] Further preferred luminescent materials include compounds represented by the following general formula (E1). [ka]

[0074] In general formula (E1), R 1 , R 3 ~R16 Each of these independently represents a hydrogen atom or a substituent (substituents include deuterium atoms). 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 or a substituent (substituents include deuterium atoms). 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 , CR15 , CR 16 It may be replaced with N.

[0075] Further preferred luminescent materials include compounds represented by the following general formula (E2). [ka]

[0076] In general formula (E2), R 1 and R 2 Each independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, R 3 ~R 16 Each of these independently represents a hydrogen atom or a substituent (substituents include deuterium atoms). 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 , CR 10 , CR 11 , CR 12 , CR 13 , CR 14 , CR 15 , CR 16 This can be replaced with N.

[0077] Further preferred luminescent materials include compounds represented by the following general formula (E3). [ka]

[0078] 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 or a substituent (substituents include deuterium atoms). 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 6At 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 them is a substituted or unsubstituted aryl group, or an acceptor group, or Z 1 and Z 2 At least one of the rings has an aryl group or an acceptor group as a substituent. 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) 1 , CR 2 , CR 3 , CR 4 , CR 5 , CR 6 , CR 7 , CR 8 , CR 9 It may be replaced with N.

[0079] Further preferred luminescent materials include compounds represented by the following general formula (E4). [ka]

[0080] In general formula (E4), Z 1 This represents a furan ring formed by the condensation of substituted or unsubstituted benzene rings, a thiophene ring formed by the condensation of substituted or unsubstituted benzene rings, or an N-substituted pyrrole ring formed by the condensation of substituted or unsubstituted benzene rings, Z 2 and Z 3 Each of these independently represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted complex aromatic ring, R 1 represents a hydrogen atom or substituent (substituents also include deuterium atoms), R 2 and R 3 Each of these independently represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.1 and R 1 , R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 They 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.

[0081] Further preferred luminescent materials include compounds represented by the following general formula (E5). [ka]

[0082] 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 or a substituent (substituents include deuterium atoms). 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 R2 , 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.

[0083] Further preferred luminescent materials include compounds represented by the following general formula (E6). [ka]

[0084] In general formula (E6), X 1 and X 2 In this example, 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 or a substituent (substituents include deuterium atoms). 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 , R9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 25 and R 26 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 , R5 and R 6 One of these elements is bonded to another to form an aromatic ring or a heteroaromatic ring.

[0085] Further preferred luminescent materials include compounds represented by the following general formula (E7). [ka]

[0086] In general formula (E7), R 201 ~R 221 Each of these independently represents a hydrogen atom or a substituent (substituents include deuterium atoms), 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 R215 , R 215 and R 216 , R 216 and R 217 , R 218 and R 219 , R 219 and R 220 , R 220 and R 221 One or two of 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). 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.

[0087] 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.

[0088] In some embodiments, the host material is selected from the group consisting of: [ka] JPEG0007923516000063.jpg214157JPEG0007923516000064.jpg46170

[0089] 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 and second TADF molecules have a difference ΔE between their lowest excited singlet energy level and the 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.

[0090] The following describes each component of the organic electroluminescent element and each layer other than the light-emitting layer.

[0091] 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.

[0092] 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.

[0093] 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 for the anode. In some embodiments, the element includes an anode and a cathode, both of which are transparent or translucent.

[0094] 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.

[0095] [ka]

[0096] Next, we will list some examples of preferred compounds that can be used as electron injection materials. [ka]

[0097] 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.

[0098] 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.

[0099] [ka]

[0100] 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.

[0101] [ka] JPEG0007923516000069.jpg192170

[0102] 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 light-emitting material, respectively.

[0103] 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.

[0104] [ka]

[0105] 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.

[0106] [ka]

[0107] Furthermore, examples of preferred compounds that can be added to each organic layer are given. For example, they can be added as stabilizing materials.

[0108] [ka]

[0109] 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.

[0110] 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).

[0111] 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.

[0112] 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.

[0113] 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.

[0114] 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.

[0115] 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.

[0116] 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.

[0117] 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.

[0118] 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.

[0119] 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]

[0120] 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 addition, the energies of HOMO and LUMO were measured by atmospheric photoelectron spectroscopy (RIKEN Instruments Co., Ltd.: AC-3, etc.). In the following synthesis examples, compounds included in general formula (1) were synthesized.

[0121] (Synthesis Example 1) Synthesis of Compound 15 Compound b [ka]

[0122] Under a nitrogen atmosphere, lithium diisopropylamide was added to a solution of compound a (37.00 mmol) in tetrahydrofuran (102 mL) and stirred for 1 hour. Then, 3.75 g (35.15 mmol) of isopropoxyboronic acid pinacol ester was added and stirred for 30 minutes. The reaction solution was cooled to -60°C and 24.65 ml of water was added to bring it back to room temperature. 6.60 g (24.65 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 5.23 g (49.31 mmol) of sodium carbonate, and 0.51 g (0.74 mmol) of bis(triphenylphosphine)palladium(II) dichloride were added and stirred at 60°C for 15 hours. After adding water and extracting with chloroform, the mixture was dried over anhydrous magnesium sulfate. The solvent was removed by distillation, and the compound was purified by silica gel column chromatography (toluene:hexane = 1:1) to obtain 3.0 g (8.19 mmol, yield 23.3%) of compound b as a white solid. 1 H NMR (400 MHz, CDCl3): δ 8.50 (d, J= 5.6Hz, 4 H), 8.66-8.62 (m, 1 H), 7.71-7.70 (m, 1 H), 7.65-7.55 (m, 6 H),2.47(d, J = 2.4 Hz,3H) ASAP MS spectral analysis: C 23 H 15 FN4: Theoretical value 366.13, Observed value 367.28

[0123] Compound 15 [ka]

[0124] Under a nitrogen atmosphere, a dimethylformamide solution (43 mL) containing 1.66 g (6.47 mmol) of 5H-benzofl[3,2-c]carbazole and 1.17 g (8.43 mmol) of potassium carbonate was stirred at room temperature for 1 hour. Then, 1.03 g (2.81 mmol) of compound b was added, and the mixture was stirred at 100°C for 17 hours. The reaction solution was allowed to return to room temperature, water was added, and the mixture was extracted with chloroform. After drying over anhydrous magnesium sulfate, the solvent was removed by distillation, and the mixture was purified by silica gel column chromatography (toluene:hexane = 7:3) followed by reprecipitation with chloroform and methanol to obtain 1.3 g (2.1 mmol, yield 74.7%) of compound 15 as a yellow solid. 1 H NMR (400 MHz, CDCl3): δ 8.67 (s, 1H), 8.10 (d, J = 6.4 Hz, 1H), 8.01 (s, 1H), 7.95-7.89 (m, 6H), 7.77 (d, J = 7.6 Hz, 1H), 7.45-7.34 (m, J = 8.0 Hz, 6H) 7.17 (t, 4H), 7.07 (d, J = 7.6 Hz, 1H), 7.00 (d, J = 8.4 Hz, 1H), 2.19 (s, 3H). ASAP MS spectral analysis: C 41 H 25 N5O: Theoretical value 603.21, Observed value 604.26

[0125] (Synthesis Example 2) Synthesis of Compound 7603 compound d [ka]

[0126] Under a nitrogen atmosphere, 5.0 g of compound c (34.49 mmol) in a tetrahydrofuran (65 ml) solution was mixed with 5.51 g (37.9 mmol) of isopropyl magnesium chloride and stirred at -80°C for 1 hour. To this mixture, 5.51 g (27.59 mmol) of 3-bromo-4-fluorobenzonitrile, 0.92 g (10.34 mmol) of copper iodide, and 2.92 g (68.98 mmol) of lithium chloride in a tetrahydrofuran (5.5 ml) solution were added, and the mixture was allowed to return to room temperature and stirred for 15 hours. The solvent was removed by distillation, the mixture was dissolved in chloroform, filtered through silica gel and Celite, and the solvent of the resulting liquid was removed by distillation to obtain 3.19 g (23.6 mmol, yield 68%) of compound d, a pale reddish-brown solid. 1 H NMR (400 MHz, CDCl3) δ7.51-7.46 (m, 2H),7.00 (t, J = 8.8Hz, 1H),

[0127] compound e [ka]

[0128] Under a nitrogen atmosphere, 3.2 g of compound d (23.68 mmol) was dissolved in tetrahydrofuran (65.78 mL), to which 22.5 ml (22.5 mmol) of 1 M lithium diisopropylamide was added and stirred for 0.5 hours. Then, 4.19 g (22.5 mmol) of isopropoxyboronic acid pinacol ester was added and stirred for 30 minutes. The reaction solution was cooled to -60°C, and 15.69 ml of water was added to bring it back to room temperature. 4.20 g (15.7 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine, 3.32 g (31.3 mmol) of sodium carbonate, and 0.33 g (0.47 mmol) of bis(triphenylphosphine)palladium(II) dichloride were added and stirred at 60°C for 15 hours. After adding water and extracting with chloroform, the mixture was dried over anhydrous magnesium sulfate. The solvent was removed by distillation, and the compound was purified by silica gel column chromatography (chloroform:hexane = 1:2) to obtain 2.28 g (6.17 mmol, yield 26.1%) of compound e as a white solid. 1 H NMR (400 MHz, CDCl3): δ 8.72 (d, J= 8.4 Hz, 4H), 8.64-8.62 (m, 1 H), 7.70-7.68 (m, 1 H), 7.63-7.55 (m, 6 H) ASAP MS spectral analysis: C 23 H 16 BF2NO2: Theoretical value 369.15, Observed value 370.40

[0129] Compound 7603 [ka]

[0130] Under a nitrogen atmosphere, a dimethylformamide solution (70.8 mL) containing 2.72 g (10.58 mmol) of 5H-benzofl[3,2-c]carbazole and 1.90 g (13.81 mmol) of potassium carbonate was stirred at room temperature for 1 hour. Then, 1.70 g (4.6 mmol) of compound e was added, and the mixture was stirred at 100°C for 15 hours. The reaction solution was allowed to return to room temperature, water was added, and the mixture was extracted with chloroform. After drying over anhydrous magnesium sulfate, the solvent was removed by distillation, followed by silica gel column chromatography (toluene:hexane = 1:2) and then autocolumn chromatography (ethyl acetate:hexane = 3:97) to obtain 0.37 g (0.6 mmol, yield 13.2%) of compound 7603 as a yellow solid. 1 H NMR (400 MHz, CDCl3): δ 8.67 (s, 1H), 8.43 (d, J = 6.8 Hz, 1H), 8.02 (s, 1H), 7.95-7.89 (m, 6H), 7.70 (d, J = 8.0 Hz, 1H), 7.44-7.33 (m, 6H) 7.17 (t, 4H), 7.07 (d, J = 7.6 Hz, 1H), 7.01 (d, J = 8.0 Hz, 1H). ASAP MS spectral analysis: C 41 H 22 D3N5O: Theoretical value 606.22, Observed value 605.26

[0131] (Synthesis Example 3) Synthesis of Compound 151775 Compound 151775 [ka]

[0132] Using 0.78 g of starting material f, 1.72 g of compound 151775 was synthesized (yield 98%) by following the same procedure as in Synthesis Example 1 and Synthesis Example 2. 1 1H NMR (400 MH) Z, CDCl3) δ 1.78 (s, 3H), 7.17-7.33 (m, 7H), 7.36-7.65 (m, 10H), 7.67 (m, 1H), 7.76 (d, J = 8.4 H Z , 1H), 7.97-8.04 (m, 7H), 8.09-8.12 (m, 1H), 8.41 (d, J = 7.6 H Z , 1H), 8.64 (d, J = 7.6 H Z , 1H), 8.93 (s, 1H), MS(ASAP+) m / z 859 [(M+H) + ].

[0133] (Example 1) Thin film fabrication and evaluation Vacuum deposition onto a quartz substrate, with a vacuum level of 1 × 10⁻⁶ -3 Compound 15 was deposited under conditions of less than Pa, forming a neat thin film of compound 15 with a thickness of 100 nm. Separately, using a vacuum deposition method on a quartz substrate, a vacuum of 1 × 10⁻¹⁰ -3 Compound 15 and PYD2Cz were deposited from different deposition sources under conditions below Pa, forming a doped thin film with a compound 15 concentration of 20% by weight and a thickness of 100 nm. Neat and doped thin films were formed in the same manner using compound 7603 and comparative compound C1 instead of compound 15. The maximum emission wavelength (λmax), photoluminescence quantum yield (PLQY), and delayed fluorescence lifetime (τ2) were measured when each doped thin film was irradiated with 300 nm excitation light. Furthermore, the HOMO energy (E) was measured using each neat thin film. HOMO ) and LUMO's energy (E LUMO ) was also measured. The results are shown in Table 6. [ka]

[0134] [Table 6]

[0135] When the τ2 of the doped thin film formed using compound 151775 instead of compound 15 according to the above procedure was also measured, it was 2.0 μs, which was extremely short. Compounds represented by general formula (1) were found to have good chromaticity, high luminescence efficiency, and a short delayed fluorescence lifetime.

[0136] (Example 2) Fabrication and evaluation 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. -5 The layers were stacked using Pa. First, HAT-CN was formed to a thickness of 10 nm on ITO, then NPD was formed to a thickness of 30 nm on top of it, and then TrisPCz was formed to a thickness of 10 nm on top of that. Next, H1 was formed to a thickness of 5 nm, and then H1 and compound 15 were co-deposited on top of it from different deposition sources to form a 40 nm thick layer which served as the light-emitting layer. The concentration of compound 15 in the light-emitting layer was 30 mass%. Next, SF3-TRZ was formed to a thickness of 10 nm, and then Liq and SF3-TRZ were co-deposited from different deposition sources to form a 30 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. The external quantum efficiency (EQE) of the fabricated organic electroluminescent device was measured and showed a high value of 14.1%. The maximum emission wavelength (λmax) was 490 nm, with x being 0.20 and y being 0.44 in the CIE XYZ color system.

[0137] (Example 3) Fabrication and evaluation of an organic electroluminescent device The only difference from Example 2 was that instead of the light-emitting layer, H1, compound 15, and the light-emitting material EM1 were deposited sequentially from different deposition sources at concentrations of 69.5% by weight, 30.0% by weight, and 0.5% by weight, respectively, to form a light-emitting layer with a thickness of 40 nm. Otherwise, the organic electroluminescent device was fabricated using the same procedure as in Example 2. Even when a compound represented by general formula (1) is used as an assist dopant, an organic electroluminescent element with good luminescence properties can be provided. [ka] [Industrial applicability]

[0138] By using a compound represented by general formula (1), an organic light-emitting element with excellent luminescence properties can be provided. Therefore, the present invention has high potential for industrial application.

Claims

1. A compound represented by the following general formula (1). 【Chemistry 1】 [In general formula (1), A represents an acceptor group represented by general formula (2) below. R １ ~R ５ At least one of them represents a cyano group. １ ~R ５ At least one of these independently represents a donor group represented by the following general formula (a). １ ~R ５ At least one of them independently represents a substituted or unsubstituted alkyl group, or a substituted or unsubstituted silyl group. The remaining R １ ~R ５ Each of these independently represents either a hydrogen atom or a deuterium atom. 【Chemistry 2】 [In general formula (2), X １ to X ３ each independently represent N or C(R), provided that at least one of X １ to X ３ is N. R represents a hydrogen atom or a substituent (the substituent also includes a deuterium atom). Ar １ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Ar ２ represents a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or when X ２ or X ３ is C(R), it bonds to said R to form an aromatic ring. L １ represents a single bond. * represents a bonding position.]] 【Transformation 3】 [In general formula (a), Z １ CR １４ Or it represents N, Z ２ CR １５ Or it represents N, Z ３ CR １６ Or it represents N, Z ４ CR １７ Or it represents N. Z ５ represents C or N, and Ar ５ R represents a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted complex aromatic ring. １４ ~R １７ Each of these independently represents a hydrogen atom or a substituent (substituents include deuterium atoms). １４ and R １５ , R １５ and R １６ , R １６ and R １７ These elements may be bonded together to form a ring structure. * indicates a bonding position.

2. R ５ The compound according to claim 1, wherein the group is a cyano group.

3. R ２ ~R ４ The compound according to claim 1 or 2, wherein one or two of them are each independently a donor group represented by the general formula (a).

4. The compound according to any one of claims 1 to 3, wherein the donor group represented by the general formula (a) is a carbazole-9-yl group condensed with benzofuran, benzothiophene, or indole, which may be substituted.

5. X １ ~X ３ A compound according to any one of claims 1 to 4, wherein is N.

6. Ar １ and Ar ２ The compound according to any one of claims 1 to 5, wherein the phenyl group may be substituted with one atom or group selected from the group consisting of deuterium atoms and phenyl groups, or a combination of two or more groups.

7. R １ ~R ５ The compound according to any one of claims 1 to 6, wherein at least one of them is an alkyl group which may be substituted with a deuterium atom.

8. R １ The compound according to any one of claims 1 to 7, wherein is a hydrogen atom.

9. A light-emitting material comprising the compound according to any one of claims 1 to 8.

10. A delayed phosphor comprising the compound according to any one of claims 1 to 8.

11. A film comprising the compound according to any one of claims 1 to 8.

12. An organic semiconductor device comprising the compound described in any one of claims 1 to 8.

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

14. The organic light-emitting element according to claim 13, wherein the element has a layer containing the compound, and the layer also contains a host material.

15. The organic light-emitting element according to claim 14, 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.

16. The organic light-emitting element according to claim 14, wherein the element has a layer containing the compound, and the layer also includes a light-emitting material having a structure different from that of the compound.

17. The organic light-emitting element according to any one of claims 14 to 16, wherein the material contained in the element has the greatest amount of light emitted from the compound.

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

19. The organic light-emitting element according to any one of claims 13 to 18, which is an organic electroluminescent element.

20. An organic light-emitting element according to any one of claims 13 to 19, which emits delayed fluorescence.

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