Compound, light-emitting material and light-emitting device

Abstract

To provide a novel compound having excellent light emission properties.SOLUTION: The present invention provides a compound of a general formula illustrated below. R1-R12 each represent a hydrogen atom, a deuterium atom or a substituent; at least one of R1-R4 represents a donor group; R represents a deuterium atom or a substituent; and n represents 0-2.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Improve the luminous efficiency of light-emitting elements such as organic electroluminescence elements (organic EL elements) In particular, research into the electrons that make up organic electroluminescence devices is being actively conducted. By developing and combining newly developed materials such as transport materials, hole transport materials, and light-emitting materials, Various efforts have been made to improve light efficiency. Among them are organic EL devices using delayed fluorescent materials. There is also research into electroluminescent elements.

[0003] In the excited state, delayed fluorescent materials undergo reverse intersystem crossing from the excited triplet state to the excited singlet state. After generating a difference, the material emits fluorescence when it returns from its excited singlet state to the ground state. Fluorescence via this pathway occurs directly from the ground state, but not from the excited singlet state (usually It is called delayed fluorescence because it is observed later than the luminescent When a compound is excited by carrier injection, the probability of generating an excited singlet state and an excited triplet state is The statistical ratio is 25%:75%, so the fluorescence from the directly generated excited singlet state alone is On the other hand, delayed fluorescent materials can emit light not only in the excited singlet state but also in the The excited triplet state can also be utilized for fluorescence emission via the reverse intersystem crossing pathway described above. Therefore, it is possible to obtain a higher luminous efficiency than that of ordinary fluorescent materials.

[0004] Since this principle was clarified, various delayed fluorescent materials have been discovered through various research efforts. Among them, benzonitriles containing nitrogen-containing heteroaromatic groups such as triazinyl groups have been used. The compound includes a compound represented by the following general formula in which rings are bonded (see Patent Document 1). X in the general formula 1 ~X 3 At least one of the Ar 1 and Ar 2 is an aryl group etc., and L 1 is a single bond or an arylene group, and R 1 ~R 4 At least one of At least one of the aryl groups is a hydrogen atom or an alkyl group. .

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

[0006] [Patent Document 1] WO2021 / 046523 Summary of the Invention [Problem to be solved by the invention]

[0007] Even if the luminescent material emits delayed fluorescence, its properties are extremely good and it is practically So far, no technology that does not have the problems mentioned above has been provided. It would be even more useful if it were possible to provide a light-emitting material with even better light-emitting properties than the optical material. For example, if it were possible to provide a light-emitting material that emits light at a shorter wavelength than the above-mentioned light-emitting materials, it would be of great industrial value. However, improvements in luminescent materials are still in the trial and error stage, and there are still many useful luminescent materials. It is not easy to generalize the chemical structure of materials.

[0008] Under these circumstances, the present inventors have developed a compound that is more useful as a light-emitting material for a light-emitting device. We have conducted extensive research with the aim of providing a compound that is more useful as a light-emitting material. We have conducted intensive research with the aim of deriving and generalizing the general formula. [Means for solving the problem]

[0009] As a result of intensive research to achieve the above object, the present inventors have found that a compound satisfying specific conditions The present invention has found that compounds having such a structure are useful as light-emitting materials. This proposal was based on the findings obtained through this research, and specifically has the following configuration:

[0010] [1] A compound represented by the following general formula (1): [ka] [In general formula (1), R 1 ~R 12 are each independently a hydrogen atom, a deuterium atom, or a substituent represents, but R 1 ~R 4 At least one of R is a donor group. represents a substituent, and n represents an integer of 0 to 2. 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 , R 11 and R 12 are bonded to each other to form a ring structure It may be possible.] [2] The compound according to [1], wherein the maximum emission wavelength is in the range of 420 nm to 475 nm. . [3] The donor group is a substituted or unsubstituted diarylamino group (provided that diaryl The two aryl groups that make up the arylamino group may be bonded to each other. [1] Or the compound according to [2]. [4] R 1 ~R 4 any one of [1] to [3], wherein at least two of The compound according to any one of claims 1 to 5. [5] The compound according to [4], wherein the at least two donor groups have the same structure. compound. [6] R 1 ~R 4 each independently represents a hydrogen atom, a deuterium atom, or a substituted or unsubstituted aryl The compound according to any one of [1] to [5], wherein the compound represents a group or a donor group. [7] R 1 and R 3

[0023] The compound according to any one of [1] to [6], wherein Compound. [8] R 2 is a substituted or unsubstituted aryl group or a donor group, [1] to [ 7]. [9] R 1 is a hydrogen atom or a deuterium atom, Compound.

[10] R 1 ~R 4 at least one of which is a substituted or unsubstituted aryl group, [1

[0023] The compound according to any one of

[10] to [9].

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

[10] .

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

[10] .

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

[10] .

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

[10] .

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

[10] .

[16] The organic light-emitting device according to

[0015] , wherein the device has a layer containing the compound, the layer also containing a host material.

[17] The layer containing the compound contains a delayed fluorescent material in addition to the compound and the host material. the lowest excited singlet energy of the delayed fluorescent material is lower than that of the host material, The organic light-emitting device according to

[16] , wherein the luminance of the compound is higher than that of the compound.

[18] The element has a layer containing the compound, and the layer is different from the compound. The organic light-emitting device according to

[16] , further comprising a light-emitting material having a structure.

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

[0016] to

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

[20] The method according to

[18] , wherein the amount of light emitted from the luminescent material is greater than the amount of light emitted from the compound. The organic light-emitting device described above.

[21] Any one of

[15] to

[20] , which is an organic electroluminescence element. The organic light-emitting element according to any one of the preceding claims.

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

[15] to

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

[0011] The compound represented by the general formula (1) has excellent light-emitting properties. The compound represented by the general formula (1) can be used to produce a light-emitting material that emits deep blue light. An excellent organic light-emitting device can be provided. DETAILED DESCRIPTION OF THE INVENTION

[0012] The present invention will be described in detail below. The present invention may be based on the representative embodiments and specific examples of the present invention. The present invention is not limited to the above embodiments and specific examples. The numerical ranges expressed by "~" include the numbers before and after as the lower and upper limits. In addition, the range includes a part of the hydrogen atoms present in the molecule of the compound used in the present invention. Or all are deuterium atoms ( 2 H, deuterium D). In chemical structural formulas, hydrogen atoms are either represented as H or omitted. When the atoms bonded to the carbon atoms constituting the ring skeleton of the benzene ring are omitted, the display is omitted. In the places where H is defined as a carbon atom constituting the ring skeleton, it is assumed that H is bonded to the carbon atom constituting the ring skeleton. In the structural formula, the deuterium atom is represented as D.

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

[0014] In general formula (1), R 1 ~R 12 are each independently a hydrogen atom, a deuterium atom, or a substituent where R 1 ~R 4 At least one of the groups is a donor group. The donor group can be selected from groups having a negative Hammett σp value. The σp value was proposed by L.P. Hammett and is the reaction It quantifies the effect of substituents on the reaction rate or equilibrium. The following equation holds between the substituents in benzene derivatives and the reaction rate constant or equilibrium constant: log(k / k0) = ρσp or log(K / K0) = ρσp In the above equation, k0 is the constant (σp) specific to the substituent in is the rate constant of the benzene derivatives, k is the rate constant of the benzene derivatives substituted with substituents, and K0 is the The equilibrium constant of the unsubstituted benzene derivative is K, and the equilibrium constant of the substituted benzene derivative is K. The equilibrium constant, ρ, represents a reaction constant determined by the type and conditions of the reaction. For explanations of the "σp value of the compound" and the values ​​of each substituent, see Hansch, C. et al., Chem. Rev., 91 , 165-195 (1991) for a description of the σp value. R 1 ~R 4 The donor group that can be taken as the group preferably has a σp of −0.3 or less, and It is more preferable that the ratio is 0.5 or less, and even more preferable that the ratio is -0.7 or less. , may be selected from a range of -0.9 or less, or may be selected from a range of -1.1 or less.

[0015] R 1 ~R 4 Among these, the number of donor groups is 1 to 4, for example, 1 to 3. For example, the number of donor groups is 1 or 2. The number of donor groups is 2 to 4. In a preferred embodiment of the present invention, at least MoR 1 is a donor group. In a preferred embodiment of the present invention, at least R 2 is a donor group In a preferred embodiment of the present invention, at least R 3 is a donor group. In an embodiment, at least R4 is a donor group. In one embodiment of the present invention, R 1 Only donors In one aspect of the present invention, R 2 In one aspect of the invention, R 3 In one embodiment of the present invention, R 4 Only the donor group is In one particularly preferred embodiment, at least R 1 and R 3 is a donor group. In one aspect, R 1 and R 3 In one embodiment of the present invention, R 1 and R 2 only is a donor group. In one embodiment of the present invention, R 1 and R 4 is the only donor group. In one embodiment, R 1 and R 2 In one embodiment of the present invention, R 2 and R 3 is In one embodiment of the present invention, R 2 and R 4 Only the donor group is In one embodiment, R 3 and R 4 In a preferred embodiment of the present invention, only At least R 1 and R 2 and R 3 is a donor group. In a preferred embodiment of the present invention, R 1 and R 2 and R 3 In one embodiment of the present invention, R 1 and R 2 and R 4 Only donors In one aspect of the present invention, R 1 and R 3 and R 4is the only donor group. In one aspect, R 2 and R 3 and R 4 In one embodiment of the present invention, R 1 ~R 4 All of the groups are donor groups. When the number of donor groups is two or more, all of the donors must be the same. In one embodiment of the present invention, the two or more donor groups are different from each other.

[0016] The donor group in the present invention is preferably a group containing a substituted amino group. or an aryl group to which a substituted amino group is bonded, particularly an aryl group to which a substituted amino group is bonded. In a preferred embodiment of the present invention, the donor group is a substituted amine. It is the base. The substituent bonded to the nitrogen atom of the substituted amino group is a substituted or unsubstituted alkyl group, a substituted or an unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or An unsubstituted heteroaryl group is preferred, and a substituted or unsubstituted aryl group or or a substituted or unsubstituted heteroaryl group. In particular, a substituted or unsubstituted diarylamino group or a substituted or unsubstituted dihet The two diarylamino groups constituting the diarylamino group are preferably diarylamino groups. The two aryl groups may be bonded to each other to form a diheteroarylamino group. The two heteroaryl groups may be bonded to each other. The "aryl group" may be a single ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of fused rings is preferably 2 to 6, for example, 2 Specific examples of the ring include a benzene ring, a naphthalene ring, an aza-substituted phenyl ring, and an aryl ring. Examples of the ring include anthracene ring, phenanthrene ring, and triphenylene ring. In embodiments, the aryl group is a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphtha group, or a substituted or unsubstituted naphthalene-1-yl group, or a substituted or unsubstituted naphthalene-2-yl group, preferably The substituent of the aryl group is, for example, a substituted or unsubstituted phenyl group. may be selected from Substituent Group B, or may be selected from Substituent Group C. Alternatively, it may be selected from Substituent Group D or Substituent Group E. In such a case, the substituents on the aryl group may be selected from the group consisting of alkyl groups, aryl groups, and deuterium atoms. In a preferred embodiment of the present invention, the aryl group is unsubstituted. . The "heteroaryl group" may be a single ring or a fused ring in which two or more rings are fused. In the case of a fused ring, the number of fused rings is preferably 2 to 6, for example For example, it can be selected from 2 to 4. Specific examples of the ring include a pyridine ring and a pyrimidine ring. rings, which may further be condensed with other rings. Specific examples of the pyridyl group include a 2-pyridyl group, a 3-pyridyl group, and a 4-pyridyl group. The heteroaryl group preferably has 4 to 40 atoms constituting the ring skeleton, and more preferably has 5 to 6 atoms constituting the ring skeleton. It is more preferable that the number is 20, and it is preferably selected in the range of 5 to 14, or more preferably selected in the range of 5 to 10. You may also choose. The "alkyl group" may be linear, branched, or cyclic. The number of carbon atoms in the alkyl group may be, for example, For example, the number of carbon atoms can be 1 or more, 2 or more, or 4 or more. The alkyl group may be 10 or less, 6 or less, or 4 or less. Specific examples of the alkyl group include a methyl group, Ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group n-pentyl, isopentyl, n-hexyl, isohexyl, 2-ethyl Hexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group, n- Nonyl group, isononyl group, n-decanyl group, isodecanyl group, cyclopentyl group, cyclo Examples of the alkyl group as a substituent include a hexyl group and a cycloheptyl group. For example, substitution with a deuterium atom, an aryl group, an alkoxy group, an aryloxy group, or a halogen atom In one aspect of the invention, the substituents on the alkyl group may be aryl groups and deuterium oxides. In a preferred embodiment of the present invention, the alkyl group is one or more selected from the group consisting of alkyl atoms. The alkyl group is unsubstituted. The "alkenyl group" may be linear, branched, or cyclic. The alkenyl group may contain two or more of the cyclic and branched moieties. For example, the number of carbon atoms can be 2 or more, 4 or more, or 30 or less, 20 or less, 10 or less, or 10 or less. The number of alkyl groups may be 6 or less, or 4 or less. Specific examples of the alkenyl group include an ethenyl group, n-propenyl group, isopropenyl group, n-butenyl group, isobutenyl group, n-pentenyl group hexenyl, isopentenyl, n-hexenyl, isohexenyl, 2-ethylhexenyl The alkenyl group as a substituent may be further substituted with a substituent. good.

[0017] R 1 ~R 4The donor group that can be used is preferably a group represented by the following general formula (a): It's nice. [ka]

[0018] In the general formula (a), Z 1 is CR 14 or N, Z 2 is CR 15 or N represents Z 3 is CR 16 or N, Z 4 is CR 17 or N. Z 5 is C or N, Ar 5 is a substituted or unsubstituted aromatic ring, or a substituted or unsubstituted complex ring. R represents a simple aromatic ring. 14 and R 15 , R 15 and R 16 , R 16 and R 17 are bonded to each other to form a ring A shaped structure may be formed.

[0019] Z 1 ~Z 4 Among 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 The number of N is 1. In one aspect of the present invention, Z 1 ~Z 4 The number of N is 0. R 14 ~R 17 each independently represents a hydrogen atom, a deuterium atom or a substituent. The substituent may be selected from, for example, Substituent Group A, or Substituent Group B. may be selected from Substituent Group C, or may be selected from Substituent Group D. , may be selected from the substituent group E. 14 ~R 17 When two or more of the following represent substituents, The two or more substituents may be the same or different. 14 ~R 17 Of It is preferred that 0 to 2 of these be substituents. For example, one of these may be a substituent, or 0 is a substituent (R 14 ~R 17 may be a hydrogen atom or a deuterium atom). R 14 and R 15 , R 15 and R 16 , R 16 and R 17 are bonded to each other to form a ring structure The cyclic structure may be any one of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring. It may be any of the rings, or may be a ring formed by condensing these rings. The aromatic ring is a substituted or unsubstituted benzene ring. The benzene ring may be condensed with another benzene ring, or may be condensed with a heterocyclic ring such as a pyridine ring. The heteroaromatic ring is an aromatic ring containing a heteroatom as a ring skeleton-constituting atom. It is preferably a 5- to 7-membered ring, for example, a 5-membered ring or a 6-membered ring. In one embodiment of the present invention, a heteroaromatic ring may be a fluorine-containing ring. In a preferred embodiment of the present invention, a benzophenone ring, a thiophene ring, or a pyrrole ring can be used. The ring structure may be a furan ring of a substituted or unsubstituted benzofuran, a substituted or unsubstituted benzofuran, The thiophene ring of benzothiophene and the pyrrole ring of substituted or unsubstituted indole. The benzofuran, benzothiophene, and indole mentioned here may be unsubstituted or substituted. It may be substituted with a substituent selected from group A, or may be substituted with a substituent selected from group B. may be substituted with a group, or may be substituted with a substituent selected from Substituent Group C It may be substituted with a substituent selected from Substituent Group D, or with a substituent selected from Substituent Group E. The nitrogen atom constituting the pyrrole ring of indole may be substituted with a substituent. It is preferred that a substituted or unsubstituted aryl group is bonded to the alkyl group. Examples of the substituent include Examples of the substituent include a substituent selected from any one of the groups A to E. may be a substituted or unsubstituted cyclopentadiene ring. R 14 and R 15 , R 15 and R 16 , R 16 and R 17 One pair of these bonds 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 1 7 are not bonded to each other to form a ring structure.

[0020] In the general formula (a), Z 5 represents C or N, and Ar 5 is a substituted or unsubstituted aromatic In one embodiment of the present invention, Z represents a ring, or a substituted or unsubstituted heteroaromatic ring. 5 is C Ri, 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 is a substituted or unsubstituted heteroaromatic ring be. Ar 5The benzene ring can be mentioned as an example of an aromatic ring that can be used. Another benzene ring may be condensed to the ring, or a heterocycle such as a pyridine ring may be condensed to the ring. Yes. Ar 5 The heteroaromatic ring is preferably a 5- to 7-membered ring, for example, a 5-membered ring. In one embodiment of the present invention, a complex ring may be used. Aromatic rings include furan ring, thiophene ring, pyrrole ring, imidazole ring, pyridine ring, and pyridine ring. In one embodiment of the present invention, Z 5 is C, and the heteroaromatic ring is a furan ring of a substituted or unsubstituted benzofuran, is the thiophene ring of unsubstituted benzothiophene, and the pyridine of substituted or unsubstituted quinoline. In one aspect of the present invention, the pyridine ring is a substituted or unsubstituted isoquinoline. , Z 5 is N and the heteroaromatic ring is a substituted or unsubstituted pyrrole ring of indole, or The imidazole ring of a substituted or unsubstituted benzimidazole. Ortho, benzothiophene, quinoline, isoquinoline, indole, and benzimidazole It may be unsubstituted, or may be substituted with a substituent selected from Substituent Group A, or It may be substituted with a substituent selected from Substituent Group B, or with a substituent selected from Substituent Group C. It may be substituted with a substituent, or may be substituted with a substituent selected from Substituent Group D. Alternatively, it may be substituted with a substituent selected from Substituent Group E.

[0021] Z in general formula (a) 5 is C, the group is represented by the following general formula (b): is preferred. [ka]

[0022] In the general formula (b), Z 1 is CR 14 or N, Z 2 is CR 15 or N represents Z 3 is CR 16 or N, Z 4 is CR 17 or N, Z 6 is C -R 18 or N, Z 7 is CR 19 or N, Z 8 is CR 20 or N represents Z 9 is CR 21 or N. R 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 are bonded to each other to form a ring structure It may be formed. Z in general formula (b) 1 ~Z 4 , R 14 ~R 17 For the corresponding general formula (a), The explanation of Z in general formula (b) can be referred to. 6 ~Z 9 , R 18 ~R 21 teeth, Z in general formula (a) 1 ~Z 4 , R 14 ~R 17 These are addressed in order, and is Z in general formula (a) 1 ~Z4 , R 14 ~R 17 You can refer to the explanation in In one aspect of the present invention, Z 1 ~Z 4 , Z 6 ~Z 9 The number of N is 0 to 2. It is preferred that Z is 0 or 1. In one embodiment of the present invention, Z 1 ~Z 4 , Z 6 ~Z 9 In a preferred embodiment of the present invention, the number of N groups is 1. 1 ~Z 4 , Z 6 ~Z 9 The number of N is 0. When it is 0, there is no substitution or represents an unsubstituted carbazol-9-yl group. The carbazol-9-yl group is an unsubstituted It may be substituted with a substituent selected from Substituent Group A, or may be substituted with a substituent selected from Substituent Group B. or may be substituted with a substituent selected from substituent group C. may be substituted with a substituent selected from Substituent Group D, or may be substituted with a substituent selected from Substituent Group D It may be substituted with a substituent selected from group E. In a preferred embodiment of the present invention, D is , a carbazole substituted with a group containing at least one substituted or unsubstituted aryl group -9-yl group, for example, substituted with at least one substituted or unsubstituted aryl group. In one embodiment of the present invention, at least one of the 2- and 7-positions is a carbazol-9-yl group. In one embodiment of the present invention, both the 3- and 6-positions are substituted or unsubstituted aryl groups. At least one of the positions is a substituted or unsubstituted aryl group. , may be unsubstituted or may be substituted with a substituent selected from Substituent Group A, It may be substituted with a substituent selected from Substituent Group B, or may be substituted with a substituent selected from Substituent Group C. It may be substituted with a substituent, or may be substituted with a substituent selected from Substituent Group D Alternatively, it may be substituted with a substituent selected from Substituent Group E.

[0023] R 1 ~R 4 The donor group that can be used is a substituted or unsubstituted indol-1-yl group. The indole ring constituting the indol-1-yl group has a fused ring, As a result, a condensed ring having four or more rings may be formed. In the present specification, a group that satisfies this condition is called a "fused indol-1-yl group."

[0024] The fused indol-1-yl group is a benzene ring or a pyrrolo ring that constitutes the indol-1-yl group. The ring fused to the alkyl ring may be one polycyclic ring, two or more polycyclic rings, or a monocyclic ring. For example, when two are fused, one is fused to the benzene ring and the other is fused to the pyrrole ring. The two fused rings may be the same or different. The number of rings may be 4 or more, 5 or more, 6 or more, or more by condensing a ring to the indole ring. The fused ring may be any of the above, and preferably has 5 or more rings. For example, a compound having four fused rings and a compound having five fused rings are Compounds with six fused rings, compounds with eight fused rings A mixture may also be employed. The ring may be fused only to the 2- and 3-positions (b) of the indole ring, or to the 4- and 5-positions (e). It may be fused only at the 5- and 6-positions (f), or at the 6- and 7-positions (g ) or both 4,5 (e) and 6,7 (g) positions. Also, either one of the 4th and 5th place (e), 5th and 6th place (f), and 6th and 7th place (g) and may be condensed at the 2- and 3-positions (b) (see the formula below, * indicates the bonding position). [ka]

[0025] The ring directly fused to the benzene ring or pyrrole ring that constitutes the indol-1-yl group (fused ring) If the ring is polycyclic, only the directly fused rings of the polycyclic rings are referred to) , an aromatic hydrocarbon ring, an aromatic hetero ring, an aliphatic hydrocarbon ring, or an aliphatic hetero ring. Preferred are those selected from the group consisting of a benzene ring and an aromatic heterocycle. This is the case when one or more rings are directly fused. The heterocycle here refers to a ring containing a heteroatom. The heteroatom is an oxygen atom, a sulfur atom, or It is preferably selected from the group consisting of silicon, nitrogen and silicon atoms, and oxygen, sulfur and More preferably, the heteroatom is selected from oxygen and nitrogen atoms. In another preferred embodiment, the heteroatom is a sulfur atom. In one embodiment, the heteroatom is a nitrogen atom. The number of heteroatoms is one or more, preferably one to three, and more preferably one or two. In a preferred embodiment, the number of heteroatoms is one. When the heteroatoms are different, they are preferably the same kind of heteroatoms, but they may be different kinds of heteroatoms. For example, two or more heteroatoms may all be nitrogen atoms. The atoms constituting the ring skeleton other than the atom B are carbon atoms. The number of atoms constituting the ring skeleton of the heterocycle directly fused to the Zene ring is 4 to 8. It is preferable that the number of carbon atoms is 5 to 7, and it is even more preferable that the number of carbon atoms is 5 or 6. In a preferred embodiment, the number of atoms constituting the ring skeleton of the heterocycle is 5. It is preferable that two or more substituted double bonds are present, and the heterocycle is fused to form an iso-substituted heterocyclic ring. It is preferable that the conjugated system of the bendole ring is extended (i.e., it has aromaticity). Preferred examples of the heterocycle include a furan ring, a thiophene ring, and a pyrrole ring. I can give it to you. The rings directly fused to the benzene ring and pyrrole ring that make up the indol-1-yl group are The fused ring may be a single ring or a fused ring. The condensed ring may be an aromatic hydrocarbon ring, an aromatic hetero ring, or an aliphatic hydrocarbon ring. and aliphatic heterocycles. In a preferred embodiment of the present invention, the benzene ring or pyridine ring constituting the indol-1-yl group At least one heterocycle is directly fused to the aryl ring. The fused ring constituting the fused indol-1-yl group contains two or more heterocycles. For example, Examples include the case where two heterocycles are contained and the case where three heterocycles are contained.

[0026] In this specification, an example of the aromatic hydrocarbon ring is a benzene ring. Examples of hetero rings include a furan ring, a thiophene ring, a pyrrole ring, a pyridine ring, a pyridazine ring, Pyrimidine ring, pyrazine ring, triazine ring, pyrrole ring, pyrazole ring, imidazole ring Examples of the aliphatic hydrocarbon ring include a cyclopentane ring, a cyclohexane ring, and the like. Examples of the aliphatic heterocycle include a piperidine ring and a cycloheptane ring. Examples of the fused ring include a pyrrolidine ring and an imidazoline ring. anthracene ring, phenanthrene ring, pyran ring, tetracene ring, indole ring, isoindole ring, benzimidazole ring, benzotriazole ring, quinoline ring, isoquinoline Examples include a phosphorus ring, a quinazoline ring, a quinoxaline ring, and a cinnoline ring.

[0027] In a preferred embodiment of the present invention, the fused indol-1-yl group is a benzofuran-fused indol-1-yl group. indol-1-yl group, benzothiophene-fused indol-1-yl group, indole-fused iodo- The present invention is directed to an indol-1-yl group, or a silaindene-fused indol-1-yl group. In a more preferred embodiment, the indol-1-yl group is a benzofuran-fused indole- 1-yl group, benzothiophene-fused indol-1-yl group, or indole-fused indol-1-yl group It is a dol-1-yl group.

[0028] In the present invention, the benzofuran-fused indol-1-yl group may be a substituted or unsubstituted A benzofuro[2,3-e]indol-1-yl group can be used. Alternatively, an unsubstituted benzofuro[3,2-e]indol-1-yl group can be used. In addition, a substituted or unsubstituted benzofuro[2,3-f]indol-1-yl group can be Substituted or unsubstituted benzofuro[3,2-f]indo A substituted or unsubstituted benzofuro[2, 3-g]indol-1-yl groups can also be used. Benzofuro[3,2-g]indol-1-yl groups can also be used. The fused ring constituting the formula (I) may or may not be further fused with a ring. In the present invention, the benzofuran-fused indol-1-yl group may be a substituted or unsubstituted A benzofuro[2,3-a]carbazol-9-yl group can be used. Substituted or unsubstituted benzofuro[3,2-a]carbazol-9-yl groups are used. In addition, substituted or unsubstituted benzofuro[2,3-b]carbazole-9-yl A substituted or unsubstituted benzofuro[3,2-b]carbonyl group can also be used. A benzoyl group such as benzoyl-9-yl may also be used. A substituted or unsubstituted 2,3-dichloro[2,3-c]carbazol-9-yl group can also be used. can also employ an unsubstituted benzofuro[3,2-c]carbazol-9-yl group The fused rings constituting these groups may or may not have further fused rings. stomach. Preferred benzofuran-fused indol-1-yl groups include those having any of the following structures: The hydrogen atoms in the following structures may be substituted or unsubstituted. For example, it may be substituted with an aryl group such as a phenyl group, or may be substituted with a carbazole group. Preferred examples include those in which the 3-position of the ring is substituted. The benzene ring in the ring may or may not be condensed with a further ring. The wavy lines indicate the bond positions. [ka]

[0029] In the present invention, the benzothiophene-fused indol-1-yl group may be a substituted or unsubstituted indol-1-yl group. A substituted benzothieno[2,3-e]indol-1-yl group can also be used. , employing a substituted or unsubstituted benzothieno[3,2-e]indol-1-yl group In addition, substituted or unsubstituted benzothieno[2,3-f]indole-1 -yl group can also be used. f] Indol-1-yl groups can also be used. A zothieno[2,3-g]indol-1-yl group can also be used. Alternatively, an unsubstituted benzothieno[3,2-g]indol-1-yl group can be employed. The fused rings constituting these groups may or may not have further fused rings. Good too. In the present invention, the benzothiophene-fused indol-1-yl group may be a substituted or unsubstituted indol-1-yl group. A substituted benzothieno[2,3-a]carbazol-9-yl group can be used. In addition, substituted or unsubstituted benzothieno[3,2-a]carbazol-9-yl groups are used. In addition, substituted or unsubstituted benzothieno[2,3-b]carbazoles can also be used. A substituted or unsubstituted benzothieno[3 ,2-b]carbazol-9-yl groups can also be used. A substituted benzothieno[2,3-c]carbazol-9-yl group can also be used. In addition, substituted or unsubstituted benzothieno[3,2-c]carbazol-9-yl groups are used. The fused rings constituting these groups may further be fused with rings, or the fused rings may be fused with rings. It is not necessary. Preferred benzothiophene-fused indol-1-yl groups include those having any of the following structures: The hydrogen atoms in the following structures may be substituted or For example, it may be substituted with an aryl group such as a phenyl group, or may be substituted with a carbazo Preferred examples include those in which the 3-position of the ring is substituted. The benzene ring in the structure may or may not have a further ring condensed thereto. stomach. [ka]

[0030] In the present invention, the indole-fused indol-1-yl group may be a substituted or unsubstituted indole-1-yl group. An indolo[2,3-e]indol-1-yl group can be used. Alternatively, an unsubstituted indolo[3,2-e]indol-1-yl group can be used. In addition, substituted or unsubstituted indolo[2,3-f]indol-1-yl groups are employed. In addition, substituted or unsubstituted indolo[3,2-f]indole-1-yl In addition, substituted or unsubstituted indolo[2,3-g]in groups can also be used. A substituted or unsubstituted indolo[3 ,2-g]indol-1-yl groups can also be used. The ring may or may not be fused with a further ring. In the present invention, the indole-fused indol-1-yl group may be a substituted or unsubstituted indole-1-yl group. The substituted aryl group can be an anthro[2,3-a]carbazol-9-yl group. Alternatively, an unsubstituted indolo[3,2-a]carbazol-9-yl group can be used. In addition, a substituted or unsubstituted indolo[2,3-b]carbazol-9-yl group is used. Substituted or unsubstituted indolo[3,2-b]carbazoles can also be used. In addition, a substituted or unsubstituted indolo[2,3- c] A carbazole-9-yl group can also be used. An anhydro[3,2-c]carbazol-9-yl group can also be used. The fused ring may or may not be further fused with a ring. Preferred indole-fused indol-1-yl groups have any of the following structures: The hydrogen atoms in the following structures may be substituted or unsubstituted. For example, it may be substituted with an aryl group such as a phenyl group, or may have a carbazole ring. In addition, the following structures are preferable examples of the substituted 3-position of the following structure: The benzene ring may or may not be condensed with a further ring. [ka]

[0031] In a preferred embodiment of the present invention, a benzofuran-fused indol-1-yl group, a benzothio phen-fused indol-1-yl groups, indole-fused indol-1-yl groups, and silaphen-fused indol-1-yl groups. The lindene-fused indol-1-yl group is substituted with a substituted or unsubstituted aryl group. Preferably, it is substituted with a substituted or unsubstituted phenyl group. The substituents of the alkyl group and phenyl group are selected from any of the substituent groups A to E. It is possible to select from the substituent group E, and it is preferable to select from the substituent group E. It is also preferable that the aryl group and phenyl group referred to in the above are unsubstituted. In this study, the fused indol-1-yl group is a phenyl group substituted with a substituted or unsubstituted aryl group. It is a benzofuran-fused indol-1-yl group.

[0032] In the following, R in general formula (1) 1 ~R 4 Specific examples of donor groups that can be used in However, the donor group that can be used in the present invention is not limited to the following specific examples. In the following specific examples, * indicates the bond position. For example, D2 has one methyl group. The hydrogenated methyl group is represented as CD3. Also, C6D5 is a group in which all hydrogen atoms are deuterium. The symbol D represents a deuterium atom. [ka] JPEG0007755298000011.jpg252169JPEG0007755298000012.jpg255169JPEG0007755298000013.jpg251170JPEG0007755298000014.jpg255170JPEG0007755298000015.jpg244168JPEG0007755298000016.jpg248170JPEG0007755298000017.jpg205170JPEG0007755298000018.jpg232150JPEG0007755298000019.jpg219166JPEG0007755298000020.jpg252168JPEG0007755298000021.jpg234155JPEG0007755298000022.jpg224168JPEG0007755298000023.jpg251170JPEG0007755298000024.jpg241169JPEG0007755298000025.jpg233168JPEG0007755298000026.jpg201170JPEG0007755298000027.jpg241170JPEG0007755298000028.jpg242168JPEG0007755298000029.jpg196170JPEG0007755298000030.jpg249159JPEG0007755298000031.jpg231170JPEG0007755298000032.jpg255170JPEG0007755298000033.jpg247170JPEG0007755298000034.jpg243170JPEG0007755298000035.jpg200170JPEG0007755298000036.jpg218170JPEG0007755298000037.jpg226170JPEG0007755298000038.jpg231167JPEG0007755298000039.jpg246170JPEG0007755298000040.jpg235170JPEG0007755298000041.jpg227170JPEG0007755298000042.jpg249170JPEG0007755298000043.jpg225170JPEG0007755298000044.jpg233170JPEG0007755298000045.jpg222170JPEG0007755298000046.jpg207170.

[0033] All hydrogen atoms in D1 to D662 are replaced with deuterium atoms to form D1( D) to D662(D). The above D1 to D662 are each a phenyl group bonded to the 3-position. (i.e., a group in which a metaphenylene group is further bonded to * in D1 to D662) is defined as D1(m) The above D1 to D662 are disclosed as a phenyl group (s) bonded to the 4-position. That is, a group in which a paraphenylene group is further bonded to * in D1 to D662) is defined as D1(p) to D 662(p) to be disclosed. In a preferred embodiment of the present invention, R in general formula (1) 1 ~R 4 The donor group that can be taken is D1 In one aspect of the present invention, R 1 ~R 4 Donors that can be obtained The carboxylic acid group is selected from the group consisting of D1(D) to D662(D). R 1 ~R 4 The donor group that can be taken is selected from the group consisting of D1(m) to D662(m). In one aspect of the present invention, R 1 ~R 4 The donor groups that can be taken are D1(p) to D662(p In one aspect of the present invention, R 1 ~R 4 The donor groups that can be taken are It is selected from the group consisting of D1 to D6. In one aspect of the present invention, R 1 ~R 4 The donor group that can be taken is selected from the group consisting of D7 to D12. In one aspect of the present invention, R1 ~R 4 The donor groups that can be taken are D13 to D83. In one aspect of the present invention, R 1 ~R 4 The donor group that can be adopted is D84 In one aspect of the present invention, R 1 ~R 4 Donors that can be obtained In one embodiment of the present invention, the carboxylic acid group is selected from the group consisting of D120 to D149. 1 ~R 4 The donor group that can be taken is selected from the group consisting of D150 to D323 and D412 to D418. In one aspect of the present invention, R 1 ~R 4 The donor groups that can be adopted are D324 to D411. In one aspect of the present invention, R 1 ~R 4 The donor group that can be taken is D4 19 to D662.

[0034] R other than the donor group in general formula (1) 1 ~R 4 is a hydrogen atom, a deuterium atom or a substituent The substituent is a substituent other than a donor group. A substituted or unsubstituted aryl group is preferred, and examples thereof include a substituted or unsubstituted phenyl group. The substituent of the aryl group (phenyl group) is selected from the substituent group E. It is also preferable that the aryl group (phenyl group) is unsubstituted. In a preferred embodiment of the invention, R 1 ~R 4 At least one of the groups is a substituted or unsubstituted aryl group. In a preferred embodiment of the present invention, R 1 ~R 4 Only one of the is substituted or unsubstituted In a preferred embodiment of the present invention, R 2 is a substituted or unsubstituted ary In one aspect of the present invention, R 1 is a substituted or unsubstituted aryl group. In one embodiment, R 3 is a substituted or unsubstituted aryl group. R 4 is a substituted or unsubstituted aryl group. In a preferred embodiment of the present invention, R 1 ~R 4 In a preferred embodiment of the present invention, at least one of R 1 ~R 4 is a hydrogen atom or a deuterium atom. , R 4 is a hydrogen atom or a deuterium atom. 1 is a hydrogen atom or In one aspect of the present invention, R 2 is a hydrogen atom or a deuterium atom. In one embodiment, R 3 is a hydrogen atom or a deuterium atom.

[0035] In a preferred embodiment of the present invention, R 1 and R 3 is a donor group, and R 2 is substituted or unsubstituted The phenyl group of R 4 is a hydrogen atom or a deuterium atom. , R 1 ~R 3 is a donor group, and R 4 is a hydrogen atom or a deuterium atom. So, R 1 and R 2 is a donor group, and R 3 is a substituted or unsubstituted phenyl group, and R 4 Water In one aspect of the present invention, R 2 and R 3 is a donor group, and R 1 is a substituted or unsubstituted phenyl group, and R 4 is a hydrogen atom or a deuterium atom. In one aspect, In one aspect of the present invention, R 1 and R 3 is a donor group, and R 2 is substituted or unsubstituted phenyl R 4 is an alkyl group. In one aspect of the invention, R 1 ~R 3 is a donor group, and R 4 is an alkyl group. In one aspect of the invention, R 1 and R 2 is a donor group, and R 3 But substitution or unsubstituted phenyl group, R 4 is an alkyl group. In one aspect of the invention, R 2 and R 3 is a donor group, and R 1 is a substituted or unsubstituted phenyl group, and R 4 is an alkyl group .

[0036] R in general formula (1) 5 ~R 12 each independently represents a hydrogen atom, a deuterium atom, or a substituent The substituent here may be a donor group. R 5 ~R 12 is a substituent The number of items can be selected from a range of 0 to 6, 0 to 4, or 0 to 2. The number may be selected within the range of 1 to 8. It is also preferable that the number is 0. You can also select it with . In general formula (1), R represents a deuterium atom or a substituent. n represents an integer of 0 to 2. n may be selected within the range of 0 to 1. . It is also preferable that it is 0. R 5 ~R 12 The substituents that R may have may be selected from, for example, the substituent group A, or It may be selected from Substituent Group B, Substituent Group C, or Substituent Group D. or may be selected from Substituent Group E.

[0037] R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 , R 11 and R 12 teeth They may be bonded to each other to form a cyclic structure. The cyclic structure may be an aromatic ring, a heteroaromatic ring, an aliphatic ring, or a cyclic structure. The ring may be either an aromatic hydrocarbon ring or an aliphatic heterocyclic ring, or may be a ring formed by condensing these rings. It is preferably an aromatic ring or a heteroaromatic ring, and more preferably an aromatic ring. The aromatic ring may be a substituted or unsubstituted benzene ring. Another benzene ring may be condensed to the ring, or a heterocycle such as a pyridine ring may be condensed to the ring. A heteroaromatic ring means a ring that exhibits aromaticity and contains a heteroatom as a ring skeleton-constituting atom, and Preferably, the ring is a 5- to 7-membered ring, and for example, a 5- or 6-membered ring is used. In one embodiment of the present invention, the heteroaromatic ring may be a furan ring or a thiophene ring. In a preferred embodiment of the present invention, the ring structure is a benzene ring. In one aspect of the present invention, R 5 and R 6 , R 6 and R7 , R 7 and R 8 One pair of In one aspect of the present invention, R 5 and R 6 , R 6 and R 7 , R 7 and R 8 One of the pairs and R 9 and R 10 , R 10 and R 11 , R 11 and R 12 One of the pairs In one embodiment of the present invention, R 5 and R 6 , R 7 and R 8 In one embodiment of the present invention, one or two of the groups are bonded to each other to form a cyclic structure. R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 , R 11 and R 12 teeth, None of them are bonded to each other to form a ring structure. R 8 and R 9 may be bonded to each other to form a linking group. In one embodiment of the present invention, the linking group is In one aspect of the invention, the linking group is -S-. In one aspect of the invention, the linking group is -O-. The group is C(R a )(R b In one aspect of the invention, the linking group is N(R c ) R a ~R c is preferably a group selected from the substituent group E. For example, R a , R b as Substituted or unsubstituted alkyl group, R c Examples of substituted or unsubstituted aryl groups include It is possible.

[0038] Specific examples of the following partial structures in general formula (1) are shown below. The partial structures that can be adopted in the present invention should not be construed as being limited to the following specific examples. In the partial structures below, * indicates the bond position. [ka]

[0039] In the following examples, methyl groups are omitted, so for example, X12 is two methyl groups. However, the deuterated methyl group is represented as CD3. Also, C6D5 represents a phenyl group in which all hydrogen atoms are deuterated. * indicates the bond position. [ka] JPEG0007755298000049.jpg241170JPEG0007755298000050.jpg144170

[0040] All hydrogen atoms in X1 to X53 are replaced with deuterium atoms to form X1(D )~X53(D). In a preferred embodiment of the present invention, the compound represented by formula (1) has X1 or X19. In one embodiment of the present invention, a group selected from the group consisting of X1 to X18 and X42 to X47 In one embodiment of the present invention, X19 to X41 and X48 to X53 are selected from the group consisting of In one embodiment of the present invention, the aryl group has a group selected from the group consisting of X2 to X9 and X15 to X31. In one embodiment of the present invention, X10, X11, X32 to X34, X42, and X In one embodiment of the present invention, X1 X2 to X14, X35 to X37, X44 to X46, and X50 to X52. In one embodiment of the present invention, a compound having a group selected from the group consisting of D42 to D53 is In one embodiment of the present invention, a group selected from the group consisting of X1(D) to X53(D) is do.

[0041] In one embodiment of the present invention, it contains at least one deuterium atom. Deuterated alkyl groups (e.g., deuterated methyl groups, deuterated ethyl groups, deuterated water groups) In one aspect of the invention, a deuterated aryl In one aspect of the invention, all hydrogen atoms are The molecule is deuterated.

[0042] The compound represented by the general formula (1) preferably does not contain a metal atom, and an atom selected from the group consisting of hydrogen atoms, deuterium atoms, nitrogen atoms, oxygen atoms, and sulfur atoms In a preferred embodiment of the present invention, the compound may be a compound represented by the general formula (1). The compound represented consists of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and oxygen atoms. The compound represented by general formula (1) is composed of only atoms selected from the group consisting of carbon atoms. atoms selected from the group consisting of hydrogen atoms, deuterium atoms, nitrogen atoms, and sulfur atoms. The compound represented by general formula (1) may be a compound consisting of only carbon atoms, water, A compound consisting of only atoms selected from the group consisting of hydrogen atoms, deuterium atoms, and nitrogen atoms. The compound represented by the general formula (1) may be a compound containing carbon atoms, hydrogen atoms, and nitrogen atoms. The compound may be composed of only atoms selected from the group consisting of The compound represented by formula (1) may contain no hydrogen atoms but may contain deuterium atoms. .

[0043] As used herein, "substituent group A" refers to a hydroxyl group, a halogen atom (e.g., fluorine), atom, chlorine atom, bromine atom, iodine atom), alkyl group (e.g., carbon number 1 to 40), oxy group (e.g., carbon number 1 to 40), alkylthio group (e.g., carbon number 1 to 40), aryl aryl groups (e.g., carbon numbers 6 to 30), aryloxy groups (e.g., carbon numbers 6 to 30), aryl Thio groups (e.g., carbon atoms of 6 to 30), heteroaryl groups (e.g., ring atoms of 5 to 30) ), heteroaryloxy groups (e.g., rings having 5 to 30 atoms), heteroarylthio groups groups (e.g., ring skeleton atoms of 5 to 30), acyl groups (e.g., carbon atoms of 1 to 40), alkenyl groups alkyl groups (e.g., carbon numbers 1 to 40), alkynyl groups (e.g., carbon numbers 1 to 40), alkoxy groups carbonyl groups (e.g., carbon numbers 1 to 40), aryloxycarbonyl groups (e.g., carbon numbers 1 to 40), heteroaryloxycarbonyl groups (e.g., carbon number 1 to 40), silyl groups (e.g., a trialkylsilyl group having 1 to 40 carbon atoms) and a nitro group; It means a group or a combination of two or more groups. In the present specification, the term "substituent group B" refers to alkyl groups (e.g., having 1 to 40 carbon atoms), alkoxy groups, and the like. oxy group (e.g., carbon number 1 to 40), aryl group (e.g., carbon number 6 to 30), aryloxy group C6-30 alkyl groups, heteroaryl groups (e.g., 5-30 ring atoms) , heteroaryloxy groups (e.g., ring skeletons having 5 to 30 atoms), diarylamino groups one or more groups selected from the group consisting of groups having 0 to 20 carbon atoms It means a combined group. In the present specification, the term "substituent group C" refers to alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups, and the like. aryl groups (e.g., 6 to 22 carbon atoms), heteroaryl groups (e.g., 5 to 20 atoms in the ring skeleton) and one selected from the group consisting of diarylamino groups (e.g., having 12 to 20 carbon atoms). It means a group or a combination of two or more groups. In the present specification, the term "substituent group D" refers to alkyl groups (e.g., having 1 to 20 carbon atoms), aryl groups, and the like. Heteroaryl groups (e.g., groups with 6 to 22 carbon atoms) and heteroaryl groups (e.g., groups with 5 to 2 atoms in the ring skeleton) 0) or a combination of two or more groups selected from the group consisting of In the present specification, the term "substituent group E" refers to alkyl groups (e.g., having 1 to 20 carbon atoms) and alkyl groups. one or more groups selected from the group consisting of aryl groups (e.g., having 6 to 22 carbon atoms); It means a combined group. In the present specification, the substitutions described as "substituted" or "substituted or unsubstituted" are The group may be selected from, for example, Substituent Group A or Substituent Group B. The substituents may be selected from the substituent group C, or may be selected from the substituent group D, or It may be selected from group E.

[0044] Specific examples of the compound represented by general formula (1) are shown in Tables 1 and 2 below. However, the compound represented by the general formula (1) that can be used in the present invention is These examples should not be interpreted as limiting. 1a) R 1 ~R 3 , Compounds 1 to 1324 are identified by specifying X for each compound. The structures of are shown separately. [ka]

[0045] In Table 1, Ph represents a phenyl group. In Table 2, each row contains the R 1 ~R 3 , X together to form the compound For example, in the column of compounds 1 to 662 in Table 2, R 2 is a phenyl group, X is fixed to X1, and R 1 and R 3 The same is D1 to D662 The compounds 1 to 662 are listed in order. , which collectively shows compounds 1 to 662 identified in Table 1. Similarly, Table 2 If the compound is 663 to 1324, R 2 is a phenyl group, and X is fixed to X19. Te, R 1 and R 3 The compounds D1 to D662 are listed in order as compounds 663 to 1324. Compounds 1325 to 3972 in Table 2 were also identified in the same manner. Compounds 3973 to 5296 in Table 2 are R 1 ~R 3 Identifies the same thing. Example For example, in the columns of compounds 3973 to 4634 in Table 2, X is fixed to X1, and R 1 ~R 3 The compounds D1 to D662 with the same structure are listed as compounds 3973 to 4634, respectively. Similarly, if X is fixed at X19 and R 1 ~R 3 are the same and are D1 to D662 These compounds are designated as compounds 4635 to 5296, in order. [Table 1] JPEG0007755298000053.jpg246140JPEG0007755298000054.jpg246139JPEG0007755298000055.jpg247140JPEG0007755298000056.jpg247140 JPEG0007755298000057.jpg246140JPEG0007755298000058.jpg246140JPEG0007755298000059.jpg245139JPEG0007755298000060.jpg246140 [Table 2]

[0046] All hydrogen atoms present in the molecules of the above compounds 1 to 5296 are replaced with deuterium atoms. These are disclosed as compounds 1(D) to 5296(D). All compounds identified by the above numbers are considered to be individually disclosed. In the above specific examples of compounds, if rotational isomers exist, the mixture of rotational isomers and the separated Each of the rotamers is also intended to be disclosed herein.

[0047] In one aspect of the present invention, a compound is selected from Compounds 1 to 5296. Now, select a compound from compounds 1(D) to 5296(D). In one aspect of the present invention, a compound is selected from compounds 1 to 1324. In this case, a compound is selected from compounds 1325 to 2648. In one embodiment of the present invention, In one embodiment of the present invention, a compound is selected from compounds 2649 to 3972. Select compounds from ~5296. In one embodiment of the present invention, a compound is selected from Compounds 1 to 662. In one embodiment of the present invention, the compound 1 is selected from compounds 663 to 1324. In one embodiment of the present invention, compounds 1987 to 2000 are selected from the group consisting of compounds 1987 to 2000. In one embodiment of the present invention, a compound is selected from compounds 2649 to 3310. In one embodiment of the present invention, a compound is selected from compounds 3311 to 3972. In one embodiment of the present invention, a compound is selected from compounds 3973 to 4634. In one embodiment of the present invention, a compound is selected from compounds 4635 to 5296. In one embodiment of the present invention, compounds 1 to 662, 1325 to 1986, 2649 to 3310, In one embodiment of the present invention, compounds 663 to 1 are selected from the group consisting of compounds 3973 to 4634. Compounds from 324, 1987-2648, 3311-3972, 4635-5296 Select .

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

[0049] The molecular weight of the compound represented by the general formula (1) is, for example, If it is intended to use an organic layer formed by vapor deposition, the viscosity should be 1500 or less. It is preferable that the ratio is 1200 or less, more preferable that the ratio is 1000 or less. The lower limit of the molecular weight is preferably 900 or less, and more preferably 900 or less. (1) is the molecular weight of the smallest compound. The compound represented by the general formula (1) may be formed into a film by a coating method regardless of its molecular weight. By using this method, it is possible to form a film even from compounds with relatively large molecular weights. The compound represented by formula (1) has the advantage of being easily soluble in organic solvents. The compound represented by the general formula (1) is easy to apply a coating method and is easy to purify to increase the purity.

[0050] By applying the present invention, a compound containing a plurality of structures represented by general formula (1) in the molecule is produced. It may also be used as a material. For example, a polymerizable group may be present in the structure represented by general formula (1) in advance, and then It is considered that the polymer obtained by polymerizing the polymerizable group of the above can be used as a light-emitting material. For example, a monomer containing a polymerizable functional group at any site of the general formula (1) is prepared. Then, it is polymerized alone or copolymerized with other monomers to produce repeating It is contemplated that a polymer having repeating units may be obtained and used as a light-emitting material. Alternatively, compounds having a structure represented by general formula (1) can be coupled together. It is also conceivable that dimers or trimers can be obtained by the above method and used as light-emitting materials.

[0051] Examples of polymers having a repeating unit containing the structure represented by general formula (1) include the following two: Examples of the polymer include a polymer having a structure represented by any one of the following general formulas: [ka]

[0052] In the above general formula, Q represents a group containing a structure represented by general formula (1), and L 1 and L 2 represents a linking group. The number of carbon atoms in the linking group is preferably 0 to 20, and more preferably 1 to 20. The number of the linking groups is preferably 15, more preferably 2 to 10. 11 -L 11 - represented by Preferably, the compound has the structure: 11 represents an oxygen atom or a sulfur atom and preferably an oxygen atom. 11 represents a linking group, and It is preferably an alkylene group or a substituted or unsubstituted arylene group, and 10 substituted or unsubstituted alkylene groups or substituted or unsubstituted phenylene groups It is more preferable to have one. In the above general formula, R 101 , R 102 , R 103 and R 104 are each independently placed Preferably, it is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, 6 substituted or unsubstituted alkoxy group, halogen atom, and more preferably 1 unsubstituted alkyl groups with 1 to 3 carbon atoms, unsubstituted alkoxy groups with 1 to 3 carbon atoms, fluorine atoms, chlorine atoms and more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms, an unsubstituted alkyl group having 1 to 3 carbon atoms, is an alkoxy group of the formula: L 1 and L 2 The linking group represented by the following formula (1) is bonded to any of the sites of Q. Two or more linking groups can be linked to one Q to form a crosslinked structure or a network structure. It may be formed.

[0053] Specific structural examples of the repeating unit include structures represented by the following formulas. [ka]

[0054] The polymer having repeating units containing these formulas has a hydrogen atom at any position of the general formula (1). A hydroxy group is introduced, and then the following compound is reacted with the hydroxy group as a linker to introduce a polymerizable group. The compound can be synthesized by introducing a compound having a polymerizable group and polymerizing the polymerizable group. [ka]

[0055] The polymer containing the structure represented by the general formula (1) in the molecule is The polymer may be a polymer consisting of only repeating units having the same structure, or a polymer consisting of repeating units having other structures. The polymer may contain a repeat unit. The repeating unit having the structure may be of a single type or of two or more types. As the repeating unit not having the structure represented by general formula (1), there are Examples of the monomers include ethylene, styrene, etc. Examples of repeating units derived from a monomer having an ethylenically unsaturated bond include Cut.

[0056] In some embodiments, the compound represented by general formula (1) is a light-emitting material. In one embodiment, the compound represented by general formula (1) can emit delayed fluorescence. It is a compound. In one embodiment of the present disclosure, the compound represented by general formula (1) is When excited by UV light, the blue region of the visible spectrum (e.g., from about 420 nm to about The preferred wavelength range of the present invention is 420 nm to 475 nm. In one embodiment, the maximum emission wavelength is in the range of 420 nm to 475 nm, for example, 420 nm The wavelength is in the range of 420 nm to 455 nm, for example, in the range of 420 nm to 440 nm. In one embodiment of the present disclosure, the compound represented by general formula (1) is When excited by It can emit light at a wavelength of approximately 510 nm. In one embodiment of the present disclosure, the compound represented by general formula (1) is Emitting light in the ultraviolet spectral region (e.g., 280-400 nm) when excited by can be done. In one embodiment of the present disclosure, an organic semiconductor device using a compound represented by general formula (1) The organic semiconductor element referred to here is an organic optical element in which light is mediated. The organic light element may be an organic element that emits light, or an organic element that does not emit light. It may be an organic light-emitting element, an organic light-receiving element that receives light, or In some embodiments of the present disclosure, the device may be an element that transfers energy by light. The compound represented by formula (1) can be used to produce an organic electroluminescence device or a solid-state imaging device ( For example, organic optical elements such as CMOS image sensors can be fabricated. In one embodiment, a CMOS (complementary metal oxide semiconductor) device using the compound represented by general formula (1) is It is possible to manufacture semiconductors, etc.

[0057] The electronic properties of small molecule chemical libraries are quantized by known ab initio methods. For example, the basis is 6-31G* and the The three-parameter Lee-Yang-Parr hybrid functional Hartree-Fock equations using time-dependent density functional theory with functional groups (TD-DFT / B3LYP / 6-31G*) and analyzed the HOMO and and molecular fragments (portions) with a LUMO below a certain threshold. do. This allows for the HOMO energy (e.g., ionization potential) of -6.5 eV or more to be reduced. The donor moiety ("D") can be selected when a valence of 0.5 eV or less is present. The acceptor moiety ("A") is selected when there is a lower LUMO energy (e.g., electron affinity) The bridge portion ("B") can, for example, hold the acceptor and donor moieties in a specific configuration. The strong conjugation between the π-conjugated systems of the donor and acceptor moieties allows for tight confinement. Prevent duplication from occurring. In one embodiment, the compound library is screened using one or more of the following properties: can be. 1. Emission around a specific wavelength 2. Calculated triplet states above a specific energy level 3. Delta E below a certain value ST value 4. Quantum yield above a certain value 5.HOMO level 6.LUMO level In one embodiment, the lowest singlet excited state and the lowest triplet excited state at 77 K are Difference (ΔE ST ) is less than about 0.5 eV, less than about 0.4 eV, less than about 0.3 eV, less than about 0.2 In some embodiments, ΔE ST The value is approximately 0.09e V, less than about 0.08 eV, less than about 0.07 eV, less than about 0.06 eV, less than about 0.05 e V, less than about 0.04 eV, less than about 0.03 eV, less than about 0.02 eV, or less than about 0.0 It is less than 1 eV. In some embodiments, the compound represented by formula (1) is present in an amount of more than 25%, for example about 30%, Approximately 35%, approximately 40%, approximately 45%, approximately 50%, approximately 55%, approximately 60%, approximately 65%, approximately 70%, The quantum yield may be about 75%, about 80%, about 85%, about 90%, about 95% or more.

[0058] [Method for synthesizing the compound represented by general formula (1)] The compounds represented by general formula (1) include novel compounds. The compound represented by general formula (1) can be synthesized by combining known reactions. For example, a carbazol-9-yl group can be introduced as a donor group at a position where the carbazol-9-yl group is to be introduced. A precursor having a fluorine atom is prepared and reacted with carbazole to obtain a carbazole. A compound having an aryl-9-yl group and represented by general formula (1) can be synthesized under the following reaction conditions: For details of this matter, reference can be made to the synthesis examples described below.

[0059] [Constructs using compounds represented by general formula (1)] In one embodiment, the compound represented by general formula (1) is combined with the compound and dispersed therein. , covalently bonded to, coated with, carried or assimilated by the compound. used with one or more materials (e.g., small molecules, polymers, metals, metal complexes, etc.) that associate with the compound. For example, the compound represented by the general formula (1) It can be combined with electroactive materials to form films. In some cases, the general formula The compound represented by (1) may be combined with a hole transporting polymer. The compound represented by formula (1) may be combined with an electron transport polymer. The compound represented by general formula (1) is combined with a hole transporting polymer and an electron transporting polymer. In some cases, the compound represented by general formula (1) may be used in combination with a hole transporting moiety and an electron transporting moiety. In the above embodiment, a solid polymer having both a hydroxyl group and a copolymer ... The electrons and / or holes formed in the film or layer are reacted with the compound represented by the general formula (1). The compound can be allowed to interact with the target compound.

[0060] [Film formation] In one embodiment, the film containing the compound represented by general formula (1) is formed by a wet process. In the wet process, a solution containing a composition containing the compound of the present invention is applied to a surface. The wet process involves spin coating, slitting, and Coating method, inkjet method (spray method), gravure printing method, offset printing method, frame printing method Examples of the wet process include, but are not limited to, photolithography. An appropriate organic solvent capable of dissolving the composition containing the compound of the present invention is selected and used. In some embodiments, the compounds included in the composition may contain substituents that increase their solubility in organic solvents. (for example, alkyl groups) can be introduced. In some embodiments, films comprising the compounds of the present invention can be formed by a dry process. In one embodiment, the dry process can be, but is not limited to, vacuum deposition. When using the vacuum deposition method, the compounds that make up the film must be separated into individual layers. Co-evaporation may be performed from a single evaporation source or from a single evaporation source containing a mixture of compounds. When a single evaporation source is used, a mixed powder of compound powders may be used. A compression molded body obtained by compressing the mixed powder of the above may be used, or a mixture obtained by heating and melting each compound and then cooling may be used. In some embodiments, the deposition rates of multiple compounds contained in a single deposition source may be adjusted. By performing co-evaporation under conditions where the weight loss rates are the same or almost the same, It is possible to form a film having a composition ratio corresponding to the composition ratio of the multiple compounds contained in the film. If a mixture of compounds with the same composition ratio as the film to be deposited is used as the deposition source, the desired In some embodiments, a film having a composition ratio can be easily formed by co-evaporation. The temperature at which each compound loses weight at the same rate was determined and used as the temperature during co-evaporation. It can be used.

[0061] [Examples of use of the compound represented by formula (1)] The compound represented by the general formula (1) is useful as a material for organic light-emitting devices. It is preferably used for photodiodes and the like. Organic Light-Emitting Diode: One aspect of the present invention is a compound represented by general formula (1) of the present invention as a light-emitting material for an organic light-emitting device. In one embodiment, the compound of the present invention represented by general formula (1) is can be effectively used as a light-emitting material in the light-emitting layer of an organic light-emitting device. The compound represented by the general formula (1) includes a delayed fluorescent material that emits delayed fluorescence. In one embodiment, the present invention provides a delayed fluorescent substance having a structure represented by general formula (1): In one embodiment, the present invention relates to the use of a compound represented by general formula (1) as a delayed fluorescent substance. In one embodiment, the present invention relates to a compound represented by general formula (1) as a host material. and can be used with one or more luminescent materials, The material may be a fluorescent material, a phosphorescent material, or a TADF material. In one embodiment, the material is represented by the general formula (1): The compound can also be used as a hole transport material. In some embodiments, the compound has the general formula ( The compound represented by formula 1) can be used as an electron transport material. The present invention relates to a method for producing delayed fluorescence from a compound represented by general formula (1). In the embodiment, an organic light-emitting device including the compound as a light-emitting material emits delayed fluorescence and has high light emission. Indicates radiation efficiency. In one embodiment, the light-emitting layer comprises a compound represented by general formula (1), In some embodiments, the substrate is a film-forming surface. In one embodiment, the compound represented by general formula (1) is The orientation affects the propagation direction of light emitted by the aligning compound, or In one embodiment, the compound represented by general formula (1) Aligning the propagation direction of the emitted light improves the light extraction efficiency from the light emitting layer. One aspect of the present invention relates to an organic light-emitting device. In some embodiments, the organic light-emitting device comprises an emissive layer. In one embodiment, the light-emitting layer contains a compound represented by general formula (1) as a light-emitting material. In some embodiments, 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 (OLED). In one embodiment, the compound represented by general formula (1) is contained in the light-emitting layer. Assisting the light emission of other light-emitting materials (as a so-called assist dopant). The compound represented by general formula (1) contained in the light-emitting layer has the lowest excited singlet energy. The lowest excited singlet energy level of the host material in the emissive layer is at the lowest excited singlet energy level. The lowest excited singlet energy level of the other light-emitting material is included in the formula (1). In some embodiments, the organic photoluminescent device includes at least one light-emitting layer. In one embodiment, the organic electroluminescent device comprises at least an anode, a cathode, and In some embodiments, the organic layer comprises at least one light-emitting layer. In some embodiments, the organic layer comprises only an emissive layer. The layer may include one or more organic layers in addition to the light-emitting layer. Examples of organic layers include a hole transport layer, ... Examples of the layer include an electron injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. In one embodiment, the hole transport layer is a hole injection transport layer having a hole injection function. The electron transport layer may be an electron injection transport layer having an electron injection function.

[0062] Emitting layer: In some embodiments, the light-emitting layer receives holes and electrons injected from the anode and cathode, respectively. recombines to form excitons. In some embodiments, the layer emits light. In some embodiments, only the light-emitting material is used as the light-emitting layer. The layer comprises an emissive material and a host material. In some embodiments, the emissive material is represented by general formula (1): In one embodiment, the organic electroluminescent device and the generation of a luminescent material to improve the light emission efficiency of organic photoluminescent devices. In some embodiments, the emissive singlet and triplet excitons are trapped within the emissive material. In addition to the light-emitting material, a host material is used in the light-emitting layer. In some embodiments, the host material is an organic In some embodiments, the organic compound has an excited singlet energy and an excited triplet energy. At least one of the energies is higher than those of the luminescent material of the present invention. In embodiments, the singlet and triplet excitons generated in the light-emitting materials of the present invention are In some embodiments, singlet and triplet excitations are confined within the molecules of the light-emitting material. The electrons are sufficiently confined to enhance light emission efficiency. The singlet and triplet excitons are sufficiently closed, while radiative efficiency is still obtained. In other words, the host material that can achieve high light emission efficiency is particularly limited. In some embodiments, the light-emitting material in the light-emitting layer of the device of the present invention may be In some embodiments, the emitted light includes both fluorescence and delayed fluorescence. In some embodiments, the emitted light comprises emitted light from a host material. The light comprises emitted light from the host material. In some embodiments, the emitted light is a compound represented by the general formula (1): In some embodiments, the emitted light includes the emitted light from the compound represented by formula (I) and the emitted light from the host material. In one embodiment, TADF molecules and a host material are used. The light-emitting layer is a polycrystalline silicon having a lower excited singlet energy than the host material in the light-emitting layer. It has a higher excited singlet energy than optical materials.

[0063] When the compound represented by the general formula (1) is used as an assist dopant, the light-emitting material (preferably Various compounds can be used as the luminescent material (preferably a fluorescent material). Examples of the materials include anthracene derivatives, tetracene derivatives, naphthacene derivatives, and pyrene derivatives. , perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, Stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, tafe Nyl derivatives, terphenylene derivatives, fluoranthene derivatives, amine derivatives, quinacride derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives thiazole derivatives, julolidine derivatives, thiazole derivatives, derivatives containing metals (Al, Zn) These exemplary skeletons may have a substituent, or the like. In addition, these exemplary skeletons may be combined with each other. In the following, a compound in combination with an assist dopant having a structure represented by general formula (1) is Examples of light-emitting materials that can be used are as follows:

[0064] [ka] JPEG0007755298000067.jpg223161JPEG0007755298000068.jpg255168

[0065] In addition, the compounds described in paragraphs 0220 to 0239 of WO2015 / 022974 are also The light-emitting material used together with the assist dopant having the structure represented by general formula (1) is Therefore, it can be particularly preferably employed.

[0066] Further preferred light-emitting materials include compounds represented by the following general formula (E1): can be done. [ka]

[0067] In general formula (E1), R 1 , R 3 ~R 16 are each independently a hydrogen atom, a deuterium atom or or a substituent. 2 represents an acceptor group, or R 1 and R 2 are combined with each other and act forming a receptor group or R 2 and R 3 are bonded to each other to form acceptor groups 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 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 may be bonded to each other to form a cyclic structure. 1 Also represents NR, and R represents a substituent. X 2 ~X 4 Of these, X 3 and X 4 At least one of is O or NR, and the rest may be O or NR or may not be linked. When the general formula is not a hydrogen atom, a deuterium atom, or a substituent, each of the two ends independently represents a hydrogen atom, a deuterium atom, or a substituent. (1) CR 1 , C.R. 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , CR 9 , C.R. 10 , C.R. 11 , C.R. 12 , C.R. 13 , C.R. 14 , C.R. 15 , C.R. 16 may be substituted with N.

[0068] Further preferred light-emitting materials include compounds represented by the following general formula (E2): can be done. [ka]

[0069] In general formula (E2), R 1 and R 2 are each independently a substituted or unsubstituted alkyl group. a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, represents R 3 ~R 16 R each independently represents a hydrogen atom, a deuterium atom, or a substituent. 1 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 2 , R 2 and R 10 , R 10 and R 11 , R 11 and R 12 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 1 are bonded to each other to form a ring structure In general formula (1), CR 3, C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 , C.R. 10 , C.R. 11 , C.R. 12 , C.R. 13 , C.R. 1 4 , C.R. 15 , C.R. 16 may be substituted with N.

[0070] Further preferred light-emitting materials include compounds represented by the following general formula (E3): can be done. [ka]

[0071] In general formula (E3), Z 1 and Z 2 each independently represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring, R 1 ~R 9 each independently represents a hydrogen atom, Represents a deuterium atom or a substituent. 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , R 8 and R 9 may be bonded to each other to form a ring structure. But Z 1 , Z 2 , R 1 and R 2 are bonded to each other to form a ring, R 2 and R3 are bonded to each other The ring formed by R 4 and R 5 are bonded to each other to form a ring, and R 5 and R 6 are bonded to each other At least one of the rings formed by the above reaction is a furan ring of a substituted or unsubstituted benzofuran, Thiophene ring of substituted or unsubstituted benzothiophene, substituted or unsubstituted indole and R 1 ~R 9 At least one of the aryl groups is substituted or unsubstituted. or Z is a terminating group or an accepting group; 1 and Z 2 At least one of the following is replaced The benzofuran ring is a ring having an aryl group or an acceptor group as a group. Among the carbon atoms constituting the benzene ring skeleton constituting the benzothiophene ring and the indole ring, The substitutable carbon atom may be substituted with a nitrogen atom. 1 , C -R 2 , C.R. 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 teeth, It may be substituted with N.

[0072] Further preferred light-emitting materials include compounds represented by the following general formula (E4): can be done. [ka]

[0073] In general formula (E4), Z 1 is a furan fused with a substituted or unsubstituted benzene ring. a thiophene ring fused with a substituted or unsubstituted benzene ring, or a substituted or unsubstituted represents an N-substituted pyrrole ring fused with a substituted benzene ring, and Z 2 and Z 3 are each independently substituted or an unsubstituted aromatic ring, or a substituted or unsubstituted heteroaromatic ring; R 1 is a hydrogen atom represents a hydrogen atom, a deuterium atom, or a substituent, and R 2 and R 3 are each independently substituted or unsubstituted represents an aryl group or a substituted or unsubstituted heteroaryl group. 1 and R 1 , R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 may be bonded to each other to form a cyclic structure, provided that , R 2 and Z 2 , Z 2 and Z 3 , Z 3 and R 3 At least one pair of these is bonded to each other to form a ring structure. It is completed.

[0074] Further preferred light-emitting materials include compounds represented by the following general formula (E5): can be done. [ka]

[0075] In general formula (E5), R 1 and R 2 are each independently a substituted or unsubstituted alkyl group. a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, represents Z 1 and Z 2 are each independently a substituted or unsubstituted aromatic ring, or a substituted or represents an unsubstituted heteroaromatic ring, and R 3 ~R 9 are each independently a hydrogen atom, a deuterium atom or a substituent. represents a substitution group, where R 1 , R 2 , Z 1 and Z 2 At least one of the following is substituted or null: Substituted benzofuran ring, substituted or unsubstituted benzothiophene ring, substituted or unsubstituted Contains an indole ring of R 1 and Z 1 , Z 1 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and Z 2 , Z 2 and R 2 , R 2 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 1 are mutually The benzofuran ring and the benzothiophene ring may be bonded to each other to form a ring structure. Among the carbon atoms constituting the benzene ring skeleton constituting the indole ring, the substitutable carbon atoms are The CR in the general formula (1) may be substituted with a nitrogen atom. 3 , C.R. 4 , C.R. 5 , C -R 6 , C.R. 7 , C.R. 8 , C.R. 9 may be substituted with N.

[0076] Further preferred light-emitting materials include compounds represented by the following general formula (E6): can be done. [ka]

[0077] In general formula (E6), X 1 and X 2 is a nitrogen atom on one side and a boron atom on the other side. R 1 ~R 26 , A 1 , A 2 are each independently a hydrogen atom, a deuterium atom, or a substituent Represents R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 , R 13 and R 14 , R 14 and R 15 , R 15 and R 16 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 19 and R 20 , R 20 and R 21 , R 21 and R 22 , R 22 and R 23 , R 23 and R 24 , R 24 and R25 , R 25 and R 26 may be bonded to each other to form a ring structure. However, X 1 is a nitrogen atom, R 17 and R 18 are bonded to each other to form a single bond A pyrrole ring is formed, and X 2 is a nitrogen atom, R 21 and R 22 are joined together to form a single bond The bond forms a pyrrole ring. 1 is a nitrogen atom, and R 7 and R 8 and R 21 and R 22 are bonded via a nitrogen atom to form a six-membered ring, and R 17 and R 18 are bonded to each other When a single bond is formed, R 1 ~R 6 At least one of the groups is substituted or unsubstituted. Is it a aryl group or R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 Noi They are bonded to each other to form an aromatic ring or a heteroaromatic ring.

[0078] Further preferred light-emitting materials include compounds represented by the following general formula (E7): can be done. [ka]

[0079] In general formula (E7), R 201 ~R 221 are each independently a hydrogen atom, a deuterium atom, or represents a substituent, and is preferably a hydrogen atom, a deuterium atom, an alkyl group, an aryl group, or an aryl group. R represents a group formed by bonding an alkyl group and an aryl group. 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 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 pairs of R 214 and R 215 , R 215 and R 2 16 , R 216 and R 217 , R 218 and R 219 , R 219 and R 220 , R 220 and R 2 21One or two of the pairs are bonded to each other to form a benzofuro structure or a benzothieno structure. More preferably, R 203 and R 204 are bonded to each other to form a benzofuro structure or benzothieno structure, and even more preferably R 203 and R 204 , R 2 16 and R 217 are bonded to each other to form a benzofuro or benzothieno structure Particularly preferably, R 203 and R 204 , R 216 and R 217 are bonded to each other to form benzofurans. It forms a benzothieno or benzothieno structure, and R 206 and R 219 is replaced or omitted a substituted aryl group (preferably a substituted or unsubstituted phenyl group, more preferably an unsubstituted phenyl group).

[0080] Furthermore, Patent Application No. 2021-103698, Patent Application No. 2021-103699, and Patent Application No. 2021 -103700, Patent Application No. 2021-081332, Patent Application No. 2021-103701, Special The patent application No. 2021-151805 and the patent application No. 2021-188860 are described in their respective specifications. The compounds represented by the general formula (1) can be used as light-emitting materials. The description and specific compounds of are incorporated herein by reference.

[0081] In some embodiments, when a host material is used, the light-emitting material in the light-emitting layer may be a material of the present invention. The amount of the transparent compound is 0.1% by weight or more. In some embodiments, when a host material is used, In this case, the amount of the compound of the present invention contained as a light-emitting material in the light-emitting layer is 1% by weight or more. In some embodiments, when a host material is used, the light-emitting material of the present invention contained in the light-emitting layer The amount of the compound is 50% by weight or less. The amount of the compound of the present invention contained as the light-emitting material in the optical layer is 20% by weight or less. In an embodiment, when a host material is used, the compound of the present invention as the light-emitting material contained in the light-emitting layer The amount of the substance is 10% by weight or less. In some embodiments, the host material of the light-emitting layer has hole-transporting and electron-transporting functionality. In some embodiments, the host material of the light-emitting layer is an organic compound that increases the wavelength of emitted light. In some embodiments, the host material of the emissive layer is an organic compound that prevents the formation of a highly vitreous It is an organic compound that has a transition temperature.

[0082] In some embodiments, the host material is selected from the group consisting of: [ka] In some embodiments, the light-emitting layer includes two or more structurally different TADF molecules. The excited singlet energy levels are higher in the order of the host material, the first TADF molecule, and the second TADF molecule. In this case, the light-emitting layer contains the first TADF molecule and the second TADF molecule. The second TADF molecule has both the lowest excited singlet energy level and the lowest excited triplet energy level at 77 K. Energy level difference ΔE ST is preferably 0.3 eV or less, and more preferably 0.25 eV or less. It is more preferable that the ion concentration is 0.2 eV or less, and it is more preferable that the ion concentration is 0.15 eV or less. It is more preferable that the ion concentration is 0.1 eV or less, and even more preferable that the ion concentration is 0.07 eV or less. It is even more preferable that the α-value is 0.05 eV or less, and even more preferable that the α-value is 0.05 eV or less. It is more preferable that the electron energy is 0.03 eV or less, and it is more preferable that the electron energy is 0.01 eV or less. It is particularly preferred that the concentration of the first TADF molecules in the light-emitting layer is higher than the concentration of the second TADF molecules. In addition, the concentration of the host material in the light-emitting layer is preferably large. The concentration of the first TADF molecules in the light-emitting layer is preferably greater than the concentration of the host It may be greater than, less than, or the same as the concentration of the material. In terms of form, the composition in the light-emitting layer is 10 to 70% by weight of the host material and 10% by weight of the first TADF molecule. In one embodiment, the first TADF molecule may be 0.1 to 30% by weight, and the second TADF molecule may be 0.1 to 30% by weight. The composition in the light-emitting layer is 20 to 45% by weight of the host material and 50 to 75% by weight of the first TADF molecule. In one embodiment, the first TADF molecule may be 5 to 20% by weight. Co-deposited film of F molecules and host material (the concentration of the first TADF molecules in this co-deposited film = A weight The photoluminescence quantum yield φPL1(A) of 100% by photoexcitation and the co-excitation of the second TADF molecule with the host material were Light emission by photoexcitation of the evaporated film (the concentration of the second TADF molecule in this co-evaporated film = A wt%) The quantum yield φPL2(A) satisfies the relation φPL1(A)>φPL2(A). In this embodiment, a co-deposited film of the second TADF molecules and the host material (the second TADF molecules in this co-deposited film) The luminescence quantum yield φPL2(B) due to photoexcitation when the concentration of DF molecules is B% by weight, and the second TAD The luminescence quantum yield φPL2(100) due to photoexcitation of a single film of F molecules is φPL2(B)>φ In one embodiment, the light-emitting layer has three different structures. The compound of the present invention can contain a plurality of TADF molecules contained in the light-emitting layer. It may be any of the compounds. In some embodiments, the light-emitting layer comprises a host material, an assist dopant, and a light-emitting material. In some embodiments, the light-emitting layer may be made of a material selected from the group consisting of gold. In some embodiments, the light-emitting layer does not contain any carbon, hydrogen, deuterium, or nitrogen atoms. A material consisting only of atoms selected from the group consisting of oxygen atoms and sulfur atoms. Alternatively, the light-emitting layer may be made of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, or the like. The material is composed of atoms selected from the group consisting of oxygen and silicon atoms. Alternatively, the light-emitting layer may be made of carbon atoms, hydrogen atoms, nitrogen atoms, and oxygen atoms. It may also be made of a material consisting only of atoms selected from the group. When the light-emitting layer contains a TADF material other than the compound of the present invention, the TADF material is Preferred delayed fluorescent materials include those described in WO2013 / 154064. Paragraphs 0008-0048 and 0095-0133 of the publication, WO2013 / 011954 Paragraphs 0007-0047 and 0073-0085 of WO2013 / 01195 No. 5, paragraphs 0007-0033 and 0059-0066, WO2013 / 0810 Paragraphs 0008-0071 and 0118-0133 of Patent Publication No. 88, and JP 2013-256 Paragraphs 0009-0046 and 0093-0134 of Patent Publication No. 490, and JP-A-2013-11 No. 6975, paragraphs 0008-0020 and 0038-0040, WO2013 / 1 No. 33359, paragraphs 0007-0032 and 0079-0084, WO2013 / Paragraphs 0008-0054 and 0101-0121 of Patent Publication No. 161437, and JP 2014 -9352, paragraphs 0007 to 0041 and 0060 to 0069, JP 2014- Paragraphs 0008-0048 and 0067-0076 of Patent Publication No. 9224, and JP 2017-1 Paragraphs 0013 to 0025 of Patent Publication No. 19663, paragraphs 0013 to 0025 of Patent Publication No. 2017-119664 0013 to 0026, paragraphs 0012 to 0025 of JP 2017-222623 A, Paragraphs 0010 to 0050 of JP 2017-226838 A and JP 2018-10041 A Paragraphs 0012 to 0043 of Publication No. 1, and paragraph 0016 of Publication No. WO2018 / 047853 Compounds encompassed by the general formulas described in 1 to 44, particularly exemplary compounds, which are delayed fluorescent compounds In addition, the following are included in the patent documents disclosed in JP 2013-253121 A and W O2013 / 133359, WO2014 / 034535, WO2014 / 115743 publication, WO2014 / 122895 publication, WO2014 / 126200 No. Publication, WO2014 / 136758 Publication, WO2014 / 133121 Publication, WO 2014 / 136860, WO2014 / 196585, WO2014 / 1 89122 publication, WO2014 / 168101 publication, WO2015 / 008580 publication Publications, WO2014 / 203840, WO2015 / 002213, WO2 015 / 016200 publication, WO2015 / 019725 publication, WO2015 / 07 2470 publication, WO2015 / 108049 publication, WO2015 / 080182 publication Patent Publication No. WO2015 / 072537, Patent Publication No. WO2015 / 080183, Patent Publication No. 20 15-129240, WO2015 / 129714, WO2015 / 129 715 publication, WO2015 / 133501 publication, WO2015 / 136880 publication , WO2015 / 137244, WO2015 / 137202, WO201 5 / 137136 publication, WO2015 / 146541 publication, WO2015 / 1595 The luminescent material described in Patent Publication No. 41, which is capable of emitting delayed fluorescence, is preferably used. It should be noted that the above publications mentioned in this paragraph are incorporated herein by reference. Quoted in.

[0083] In the following, each component of the organic electroluminescence element and each layer other than the light-emitting layer We will explain about this.

[0084] Base material: In some embodiments, the organic electroluminescent device of the present invention is supported by a substrate. The substrate is not particularly limited, and may be any substrate generally used in organic electroluminescence devices. For example, glass, transparent plastic, quartz, and silicon may be used. Either material may be used.

[0085] anode: In some embodiments, the anode of the organic electroluminescent device is made of a metal, an alloy, In some embodiments, the conductive material is made from a conductive compound or a combination thereof. Some metals, alloys, or conductive compounds have high work functions (4 eV or more). In some embodiments, the metal is Au. In some embodiments, the conductive transparent material is C Selected from uI, indium tin oxide (ITO), SnO2 and ZnO. In some embodiments, 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 formed by evaporation or sputtering. In some embodiments, the film is patterned by photolithographic methods. In some embodiments, the pattern does not need to be highly accurate (e.g., about 100 μm). In the case of a pattern having a shape suitable for deposition or sputtering onto an electrode material, In some embodiments, the coating may be formed using a mask, such as an organic conductive compound. When a coating material can be applied, wet film forming methods such as printing and coating methods are used. In some embodiments, when radiation passes through the anode, the anode is 10% The anode has a sheet resistance of less than several hundred ohms 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. Varies depending on the materials used.

[0086] cathode: In some embodiments, the cathode is a metal with a low work function (4 eV or less) (electrode The electrode is made of an electrode material such as a conductive metal (called an electron-injected metal), alloy, conductive compound, or a combination thereof. In some embodiments, the electrode material is sodium, sodium-potassium magnesium 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 and rare earth elements. In some embodiments, the electron-injecting metal and the electron-injecting gold A mixture of the metal and a second metal, which is a stable metal with a higher work function than the metal, is used. In some embodiments, the mixture is a magnesium-silver mixture, a magnesium-aluminum mixture, or a mixture of magnesium and silver. magnesium mixture, magnesium-indium mixture, aluminum-aluminum oxide (Al 2O3) mixture, lithium-aluminum mixture, and aluminum. In some embodiments, the mixture provides improved electron injection properties and resistance to oxidation. In some embodiments, the cathode is formed by depositing the electrode material as a thin film by evaporation or sputtering. In some embodiments, the cathode is formed by forming a In some embodiments, the cathode has a sheet resistance of several hundred ohms or less. In some embodiments, the thickness of the cathode is 50 to 200 nm. In some embodiments, an organic electroluminescent In some embodiments, either the anode or the cathode of the element is transparent or semi-transparent. In this case, transparent or semi-transparent electroluminescent elements enhance light radiance. In some embodiments, the cathode is made of a conductive, transparent material as described above for the anode. In some embodiments, the cathode is formed from a transparent or semi-transparent material. In the conventional organic light-emitting diode (OLED), the device comprises an anode and a cathode, both of which are transparent or semi-transparent.

[0087] Injection layer: The injection layer is a layer between the electrode and the organic layer. In some embodiments, the injection layer is a drive In some embodiments, the injection layer is a positive electrode. The hole injection layer and the electron injection layer are disposed between the anode and the light emitting layer or the hole transport layer. and between the cathode and the light-emitting layer or the electron-transporting layer. In some embodiments, an injection layer is present. In some embodiments, an injection layer is not present. Preferred examples of compounds that can be used as the hole injection material are listed below.

[0088] [ka]

[0089] Next, examples of preferred compounds that can be used as the electron injection material will be given. [ka]

[0090] Barrier layer: The blocking layer prevents the charges (electrons or holes) and / or excitons present in the light-emitting layer from In some embodiments, the electron barrier layer is a layer that can prevent the electrons from diffusing out of the It exists between the light-emitting layer and the hole-transporting layer and prevents electrons from passing through the light-emitting layer to the hole-transporting layer. In some embodiments, the hole blocking layer is between the light-emitting layer and the electron-transporting layer, Blocks holes from passing through the light-emitting layer to the electron-transporting layer. The wall layers prevent excitons from diffusing outside the light-emitting layer. The electron blocking layer and the hole blocking layer constitute an exciton blocking layer. The term "layer" or "exciton blocking layer" refers to a layer that has both the functions of an electron blocking layer and an exciton blocking layer. It includes a layer that

[0091] Hole blocking layer: The hole blocking layer functions as an electron transport layer. In some embodiments, during electron transport In some embodiments, the hole blocking layer prevents holes from reaching the electron transport layer. The blocking layer increases the probability of recombination of electrons and holes in the light-emitting layer. The material can be the same materials as those described above for the electron transport layer. Preferred examples of compounds that can be used in the hole blocking layer are listed below.

[0092] [ka]

[0093] Electron barrier layer: The electron blocking layer transports holes. In some embodiments, the electron blocking layer The layer blocks electrons from reaching the hole transport layer. In some embodiments, the electron blocking layer comprises: The electron blocking layer is made of a material that increases the probability of recombination of electrons and holes in the light-emitting layer. It may be the same materials as those previously described for the transport layer. Specific examples of preferred compounds that can be used as electron blocking materials are listed below.

[0094] [ka]

[0095] Exciton blocking layer: The exciton blocking layer prevents excitons generated through the recombination of holes and electrons in the light-emitting layer from transporting charges. In some embodiments, the exciton blocking layer is In some embodiments, this allows for efficient confinement of excitons in the In some embodiments, the exciton blocking layer is disposed on the anode side and the light emitting efficiency of the device is improved. adjacent to the light-emitting layer on either side of the cathode and on both sides thereof. When the exciton blocking layer is present on the anode side, the layer is present between the hole transport layer and the light emitting layer; In some embodiments, an exciton blocking layer is located on the cathode side. When the cathode is formed, the layer 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, an electron blocking layer, or a similar layer is provided between the anode and the light-emitting layer on the anode side. In some embodiments, the hole injection layer, the electron blocking layer, A blocking layer, hole blocking layer or similar layer may be present between the cathode and an exciton blocking layer adjacent to the light-emitting layer on the cathode side. In some embodiments, the exciton blocking layer is between the excited singlet energy and at least one of which includes an excited triplet energy of the light-emitting material, higher than the excited triplet energy.

[0096] 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 hole injection or transport properties and electron blocking properties. In some embodiments, the hole transport material has one of the following properties: In some embodiments, the hole transport material is an inorganic material. Examples of known hole transport materials include, but are not limited to, triazole derivatives, oxadiazo azole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, Polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, allylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrene derivatives Lylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, Silazane derivatives, aniline copolymers and conductive polymer oligomers (especially thiophene oligomers), or combinations thereof. In some embodiments, the hole transport material is selected from porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as hole transport materials are listed below.

[0097] [ka]

[0098] 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 transports electrons injected from the cathode to the light-emitting layer. In some embodiments, the electron transport material also functions as a hole blocking material. Examples of electron transport layers that can be used in the present invention include, but are not limited to, nitro Substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbo Diimides, fluorenylidenemethane derivatives, anthraquinodimethanes, anthrone derivatives, oxadiazole derivatives, azole derivatives, azine derivatives or combinations thereof; In some embodiments, the electron transport material is a thiadiazole derivative. or a quinoxaline derivative. In some embodiments, the electron transport material is a polymeric material. Specific examples of preferred compounds that can be used as electron transport materials are listed below. do.

[0099] [ka]

[0100] Furthermore, examples of compounds that can be added to each organic layer include: It is conceivable to add it as a material.

[0101] [ka]

[0102] Specific examples of preferred materials that can be used in organic electroluminescence devices However, the materials that can be used in the present invention are limited to the following exemplary compounds. In addition, even if a compound is given as an example of a material having a specific function, It is also possible to use it as a material having other functions.

[0103] device: In some embodiments, the light-emitting layer is incorporated into a device. For example, the device may include , OLED bulbs, OLED lamps, TV displays, computer monitors , including but not limited to mobile phones and tablets. In some embodiments, the electronic device comprises an anode, a cathode, and a The present invention also includes an OLED having at least one organic layer including a light-emitting layer therebetween. In some embodiments, the compositions described herein can be used in OLED or optoelectronic devices. The present invention can be incorporated into various photosensitive or photoactivated devices, such as lasers. In the present invention, the composition is useful for facilitating charge or energy transfer within the device and / or can be useful as a hole transport material. Such devices include, for example, organic light-emitting diodes. Organic integrated circuits (OLEDs), organic field-effect transistors (O-FETs), Organic thin film transistor (O-TFT), organic light emitting transistor (O-LET), organic solar battery (O-SC), organic optical detector, organic photoreceptor, organic magnetic field quencher (field- quench device (O-FQD), light-emitting fuel cell (LEC) or organic laser diode Examples include O-laser.

[0104] Bulb or Lamp: In some embodiments, the electronic device comprises an anode, a cathode, and a gap between the anode and the cathode. It includes an OLED that includes at least one organic layer, including a light-emitting layer. In some embodiments, the device includes OLEDs of different colors. In some embodiments, the device comprises an array comprising a combination of OLEDs. The combination of LEDs is a three-color combination (e.g., RGB). , the combination of OLEDs is not red, green or blue (e.g. orange and In some embodiments, the OLED combination is a two-color, four-color, It is a combination of one or more colors. In some embodiments, the device comprises: a first surface having a mounting surface and a second surface opposite thereto, and at least one opening a circuit board defining the At least one OLED on the mounting surface, D is at least one active layer including an anode, a cathode, and a light-emitting layer between the anode and the cathode; At least one OLED having a light-emitting configuration including an organic layer; a housing for the circuit board; At least one connector disposed at an end of the housing, wherein the casing and the connector define a package suitable for attachment to a lighting fixture; It is an OLED light with one connector and one LED. In some embodiments, the OLED light is configured to emit light in multiple directions. In some embodiments, the first direction includes a plurality of OLEDs attached to a circuit board. Some of the light emitted in the reflector is polarized and emitted in a second direction. A projector is used to polarize light emitted in a first direction.

[0105] Display or Screen: In some embodiments, the light-emitting layer of the present invention can be used in a screen or display. In some embodiments, the compounds of the present invention can be prepared by methods such as, but not limited to, vacuum evaporation. They are deposited onto a substrate using processes such as deposition, evaporation, or chemical vapor deposition (CVD). In one embodiment, the substrate is etched on two sides to provide pixels of unique aspect ratios. The screen (also called a mask) is a photoplate structure useful in is used in the manufacturing process of OLED displays. The design results in very steep, narrow tie bars between pixels vertically and horizontally. This allows for the placement of large, wide-area beveled apertures on the TFT backplane. While optimizing chemical vapor deposition of the This makes it possible to configure the network. Internal pixel patterning allows for three-dimensional display with various aspect ratios in both horizontal and vertical directions. It is possible to construct a 2-dimensional pixel aperture. The use of "stripes" or halftone circles undercuts these particular patterns. Etching in specific areas is prevented until the material is removed from the substrate. The cell area is etched at a similar rate, but its depth is different from the halftone pattern. By changing the size and spacing of the halftone patterns, This allows etching with different passivation rates within the filter, which is necessary to create steep vertical bevels. This allows for deep, localized etching. The preferred material for deposition masks is Invar, which is cut into long thin sheets at steel mills. Invar is a metal alloy that is cold rolled into a shape. Invar is then spun onto a mandrel as a nickel mask. It is not possible to electrodeposit it onto a suitable, low-cost material for forming open areas in a deposition mask. The first method is by wet chemical etching. In some embodiments, the screen or display pattern is a pixel on a substrate. In some embodiments, the screen or display pattern is Lithography (e.g., photolithography and e-beam lithography) In some embodiments, the screen or display pattern is fabricated using wet chemical etching. In a further embodiment, the screen or The display pattern is fabricated using plasma etching.

[0106] Device manufacturing method: OLED displays are generally made by forming a large mother panel, which is then The panels are manufactured by cutting them into cell panels. Usually, Each cell panel is formed on a base substrate with a thin film transistor having an active layer and source / drain electrodes. A thin film transistor (TFT) is formed, a flattening film is applied to the TFT, and pixel electrodes and light-emitting layer, counter electrode and encapsulation layer are sequentially formed and cut from the mother panel. It is formed by OLED displays are generally made by forming a large mother panel, which is then The panels are manufactured by cutting them into cell panels. Usually, Each cell panel is formed on a base substrate with a thin film transistor having an active layer and source / drain electrodes. A thin film transistor (TFT) is formed, a flattening film is applied to the TFT, and pixel electrodes and light-emitting layer, counter electrode and encapsulation layer are sequentially formed and cut from the mother panel. It is formed by

[0107] Another aspect of the present invention provides a method for manufacturing an organic light emitting diode (OLED) display. The method comprises: forming a barrier layer on a base substrate of the mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer on each of the display units of the cell panel; The degree, and applying an organic film to the interface between the cell panels. In some embodiments, the barrier layer is an inorganic film, for example formed of SiNx. The edges of the barrier layer are covered with an organic film made of polyimide or acrylic. In some embodiments, the organic film is formed so that the mother panel can be softly cut into individual cell panels. Assist in ensuring this is done. In some embodiments, the thin film transistor (TFT) layer comprises a light-emitting layer, a gate electrode, and , and source / drain electrodes. Each of the plurality of display units has a thin film transistor. a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a thin film transistor (TFT) layer and a light-emitting unit formed on the interface portion. The film is made of the same material as the planarizing film and has the same shape as the planarizing film. In some embodiments, the light-emitting unit comprises a passivation layer and The planarization film between them and the encapsulation layer that covers and protects the light-emitting unit form the TF In some embodiments of the manufacturing method, the organic film is connected to a T layer. It is not connected to the spray unit or the encapsulation layer.

[0108] Each of the organic film and the planarizing film is made of one of polyimide and acrylic. In some embodiments, the barrier layer may be an inorganic film. In some embodiments, the base substrate may be formed of polyimide. Furthermore, before forming a barrier layer on one surface of the base substrate formed of polyimide, Attaching a carrier substrate made of a glass material to another surface of the base substrate; and separating the carrier substrate from the base substrate before cutting along the interface portion. In some embodiments, the OLED display is a flexible It is a powerful display. In some embodiments, the passivation layer is disposed on the TFT layer to cover the TFT layer. In some embodiments, the planarization film is a passivation organic film. In some embodiments, the planarization film is an organic film formed on the planarization layer. The barrier layer is made of polyimide or acrylic, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarization film is used in the manufacture of an OLED display. and the organic film are simultaneously formed. In some embodiments, the organic film is , may be formed at the edge of the barrier layer, so that a portion of the organic film is directly connected to the base. The remaining portion of the organic film contacts the substrate and surrounds the edge of the barrier layer. Touch.

[0109] In some embodiments, the light-emitting layer comprises a pixel electrode, a counter electrode, and a and an organic light-emitting layer disposed between the electrode and the counter electrode. The pixel electrodes are 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, the pixel An appropriate voltage is applied between the cathode and counter electrodes, causing the organic light-emitting layer to emit light. Hereinafter, an image-forming unit having a TFT layer and a light-emitting unit will be referred to as an image-forming unit. The display unit is called a display unit. In some embodiments, the display unit is covered to prevent penetration of external moisture. The encapsulation layer is a thin film encapsulation layer in which organic and inorganic films are alternately laminated. In some embodiments, the encapsulation layer may be formed into a structure comprising multiple thin films. In some embodiments, the interface has a laminated thin-film encapsulation structure. The organic film is disposed at intervals with respect to each of the plurality of display units. In some embodiments, the organic film is a film in which a portion of the organic film is directly based on the base group. the remaining portion of the organic film contacts the barrier layer while surrounding the edge of the barrier layer. It is formed in the following manner.

[0110] In one embodiment, the OLED display is flexible and formed from polyimide. In some embodiments, the base substrate is a glass material. The adhesive is formed on a carrier substrate formed in step (b), and the carrier substrate is then 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, a base substrate is formed on all surfaces of the mother panel, while a barrier layer is formed on each cell. The barrier layer is formed according to the size of the cell panel, thereby reducing the interface between the barrier layers of the cell panel. A groove is formed in the groove portion of each cell panel, and each cell panel can be cut along the groove.

[0111] In some embodiments, the manufacturing method further comprises cutting along the interface. a step of forming a groove in the barrier layer and forming at least a portion of the organic film in the groove; In some embodiments, the TF of each cell panel is The T layer is formed, and the inorganic passivation layer and the organic planarization film are The TFT layer is then covered with a flat film made of, for example, polyimide or acrylic. At the same time as the protective film is formed, the grooves at the interface are filled with, for example, polyimide or The cell panels are covered with an acrylic organic film. When cutting along the grooves, the organic film absorbs the shock that occurs, preventing cracks. That is, all the barrier layers are completely exposed without any organic film. In this case, when each cell panel is cut along the groove at the interface, the resulting impact This increases the risk of cracks being transmitted to the layers. In this case, the grooves at the interface between the barrier layers are covered with an organic film, and the organic film is not present. To absorb the shock that would otherwise be transmitted to the barrier layer, each cell panel is softly cut and the barrier layer is In one embodiment, the grooves of the interface may be covered. The organic film and the planarizing film are spaced apart from each other. If the film and the planarization film are connected to each other as one layer, the planarization film External moisture will not penetrate the display unit through the film and the remaining organic film. The organic film and planarizing film must be installed in a location where the organic film is They are spaced apart from each other so as to be spaced apart from the playing units.

[0112] In some embodiments, the display unit is formed by forming a light-emitting unit. an encapsulation layer disposed on the display unit to cover the display unit; This allows the mother panel to be fully manufactured before it is placed on the carrier that carries the base substrate. The rear substrate is separated from the base substrate. When irradiated onto the base substrate, the carrier substrate is heated to a temperature equal to the thermal expansion coefficient between the carrier substrate and the base substrate. The difference separates it from the base substrate. In some embodiments, the mother panel is cut into cell panels. In an embodiment, the mother panel is cut along the interface between the cell panels using a cutter. In some embodiments, the mother panel is cut along an interface. The grooves in the base are covered with an organic film, which absorbs the impact during cutting. In some embodiments, the barrier layer can be prevented from cracking during cutting. In some embodiments, the method reduces product defect rates and stabilizes product quality. . Another embodiment is a barrier layer formed on a base substrate and a display formed on the barrier layer. The unit, the encapsulation layer formed on the display unit, and the barrier layer are applied to the edge of the unit. and an organic film formed on the substrate. [Example]

[0113] The following synthesis examples and working examples will further illustrate the features of the present invention. The materials, processing contents, processing procedures, etc. may be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. The light emission characteristics were evaluated using a source meter (Keithley: 2400 series), Semiconductor parameter analyzer (Agilent Technologies: E5273A), optical Power meter measuring device (Newport: 1930C), optical spectrometer (Ocean Optic) A spectroradiometer (Topcon: SR-3) and a streamlined The measurement was carried out using a photochromic camera (Model C4334 manufactured by Hamamatsu Photonics KK). In the following synthesis examples, compounds within the general formula (1) were synthesized.

[0114] (Synthesis Example 1) Synthesis of Compound 6 [ka]

[0115] Compound A (WO2019 / 190223A1, 0.94 g, 3.55 mm ol), Compound B (WO2019009052A1, 0.90g, 2.96mmol), Potassium phosphate 1.57 g (7.40 mmol), X-Phos (0.14 g, 0.30 A solution of 1 mmol of tris(dibenzylideneacetone)diparadiamine in toluene (7.4 mL) was The reaction solution was refluxed for 16 hours. The mixture was returned to a warm temperature, water was added, and the mixture was extracted with chloroform, and then dried over anhydrous magnesium sulfate. The residue was evaporated and purified by silica gel column chromatography (chloroform:hexane=1:3). As a result, 0.72 g (1.77 mmol, yield 60%) of compound C was obtained as a yellow solid. 1 H-NMR (500 MHz; CDCl3): δ 8.72 (d, J= 8.0 Hz, 2H), 7.91 (t, J = 7.4 Hz, 1H), 7.75 (t, J = 8.0 Hz, 2H), 7.58 (d, J = 8.5 Hz, 2H), 7.43 (t, J = 7.4 Hz, 2H), 7. 36 (s, 2H), 7.17 (t, J = 9.2 Hz, 1H). ASAP MS Spectral Analysis: C 25 H 12 BF2NO2: Theoretical value 409.09 Observed value 408.08

[0116] Compound C (1.10 g, 2.70 mmol), bromobenzene (0.63 g, 4.05 mmol), potassium carbonate (0.75 g, 5.40 mmol), 2-ethyl Hexanoic acid (0.078 g, 0.54 mmol), tricyclohexylphosphine (0. 11 g, 0.41 mmol) in xylene solution (8.1 mL) 1640648531309_862 (0.095 g, 0.16 mmol) was added, and the reaction solution was stirred at 110° C. for 13 hours. The mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation, and the mixture was recrystallized from toluene to give 0.79 g (1.63 mmol) of Compound D as a gray-white solid. l, yield 60%). 1 H-NMR (500 MHz; CDCl3): δ 8.72 (d, J= 7.5 Hz, 2H), 7.88 (t, J = 7.5 Hz, 1H), 7.75 (t, J = 7.5 Hz, 2H), 7.58 (d, J = 8.4 Hz, 2H), 7.54-7.52 (m, 5H), 7.43 (t, J = 7.5 Hz, 2H), 7.40 (s, 2H). ASAP MS Spectral Analysis: C 31 H 16 BF2NO2: Calculated 483.12, Observed 484.21

[0117] Under a nitrogen atmosphere, 3,6-diphenyl 9H-carbazole (0.46 g, 1.43 mmol) ), sodium hydride (60 wt%, 0.066 g, 1.67 mmol) tetrahydro The furan solution (3.0 mL) was stirred at room temperature for 1 hour, and then compound D (0.23 g, 0.48 mm The reaction solution was cooled to room temperature and added with saturated ammonium chloride. The mixture was extracted with chloroform and then dried over anhydrous magnesium sulfate. The product was purified by silica gel column chromatography (chloroform:hexane = 2:3). The residue was purified by reprecipitation (chloroform / methanol) to obtain Compound 6 as a pale yellow solid. 0.25g (0.23mmol, yield 49%) was obtained. 1 H-NMR (500 MHz; CDCl3): δ 8.61 (d, J= 7.5 Hz, 2H), 8.37 (s, 1H), 8.29 (s, 2H) , 8.11 (s, 2H), 7.72-7.56 (m, 16H), 7.51-7.30 (m, 16H), 7.20 (d, J = 8.4 Hz, 2H) , 7.10 (s, 2H), 6.65 (d, J= 7.5 Hz, 2H), 6.57 (t, J = 7.5 Hz, 1H), 6.48 (t, J = 7.5 Hz, 2H). ASAP MS Spectral Analysis: C 79 H 48 BN3O2: Calculated 1081.38, Observed 1081.73

[0118] (Synthesis Example 2) Synthesis of Compound 3973 [ka]

[0119] 5-Bromo-2,3,4-fluorobenzonitrile (2.83 g, 12.0 mmol) and bis(pinacolato)diboron (3.67 g, 14.4 mmol) of 1,4-dioxa A solution of 1,1'-bis(diphenylphosphino)ferrocene in 120 mL of chloroform and [1,1'-bis(diphenylphosphino)ferrocene]dichloro Palladium(II) (0.44 g, 0.60 mmol), potassium acetate (2.36 g, 2 4.0 mmol) was added under a nitrogen stream and stirred at 110°C. After 15 hours, the reaction mixture was The mixture was heated to room temperature and then added to compound E (4.39 g, 14.4 mmol), tris(dibenzylidene acetone), and Dipalladium(0) (1.10 g, 1.20 mmol), 2-dicyclohexylphosphite phenyl-2',6'-dimethoxybiphenyl (0.99 g, 2.40 mmol) and sodium carbonate Sodium (3.18 g, 30.0 mmol) was added, and the mixture was stirred at 80°C for 15 hours. The mixture was returned to room temperature, the solvent was distilled off, and the residue was washed with methanol. The pale yellow solid compound F was purified by chromatography (toluene:hexane = 1:2) to give 1. 0.4g (2.46mmol, yield 21%) was obtained. 1 H-NMR (500 MHz, CDCl3): δ 8.72 (d, J= 7.5 Hz, 2H), 7.76 (t, J = 7.5 Hz, 2H), 7.68 (t, J = 7.0 Hz, 1H), 7.58 (d, J = 8.5 Hz, 2H), 7.44 (t, J = 7.5 Hz, 2H), 7. 34 (s, 2H). ASAP mass spectrometry: theoretical value 425.08, observed value 426.21.

[0120] Compound F (1.04 g, 2.46 mmol), 9H-carbazole (2.09 g, 12 0.5 mmol) and sodium hydride (0.43 g, 18.0 mmol) were added to N,N-dimethylformamide The reaction solution was added to 25 mL of methylformamide and stirred at 100°C for 20 hours. Water was added, and the precipitate was filtered off. The filtered product was washed with methanol and dried under vacuum. The resultant was purified by silica gel column chromatography (hexane:toluene=1:1, toluene:acetic acid The compound 3973 was purified by elution with ethyl acetate (9:1) to give 1.10 g (1.27 mmol) of a yellow solid. The product was obtained in a 76% yield. 1 H-NMR (400 MHz, CDCl3): δ 8.35 (s, 1H), 8.19 (d, J = 7.7 Hz, 2H), 8.05 (s, 1H ), 7.69-7.67 (m, 4H), 7.54 (t, J = 7.7 Hz, 2H), 7.46 (t, J = 7.6 Hz, 2H), 7.40-7 .34 (m, 5H). ASAP mass spectrum analysis: Calculated 866.29, observed 867.41

[0121] (Synthesis Example 3) Synthesis of Compound 1 In the same manner, the following compound 1 was synthesized. [ka]

[0122] (Synthesis Example 4) Synthesis of Compound 668 In the same manner, the following compound 668 was synthesized. [ka]

[0123] (Synthesis Example 5) Synthesis of Compound 663 In the same manner, the following compound 663 was synthesized. [ka]

[0124] (Example 1) Preparation and evaluation of thin films Vacuum deposition method on a quartz substrate at a vacuum level of 1 x 10 -3 Compound 6 and PY were D2Cz was evaporated from a different evaporation source, and a doped thin film with a concentration of compound 6 of 20 wt% was obtained. It was formed to a thickness of 100 nm. Instead of compound 6, compound 1, compound 3973, compound 668, compound 663, and comparison Doped thin films were formed in the same manner using Compound 1 and Comparative Compound 2. When Compound 1 and Comparative Compound 2 were used, mCBP was used in place of PYD2Cz. The maximum emission wavelength (λmax) when each doped thin film was irradiated with 300 nm excitation light. The results are shown in Table 3. All of the compounds represented by general formula (1) were comparative compounds. It has a maximum emission wavelength on the shorter wavelength side than Compound 1 and Comparative Compound 2, and emits in the blue emission region. In addition, the photoluminescence quantum yield (PLQY) of compound 3973 was measured. The emission from Compound 1, Compound 6, and Compound 3973 was slow. It was also confirmed that the fluorescence was delayed. [ka]

[0125] [Table 3]

[0126] (Example 2) Fabrication and evaluation of organic electroluminescence device A glass substrate with an anode made of 50 nm thick indium tin oxide (ITO) Each thin film was deposited on the plate by vacuum deposition at a vacuum of 5.0 x 10 -5 First, the IT HAT-CN was formed on O to a thickness of 10 nm, and NPD was formed on it to a thickness of 35 nm. Then, PTCz was formed on it to a thickness of 10 nm. The resulting layer was co-evaporated from the evaporation source to form a layer with a thickness of 40 nm, which served as the light-emitting layer. The concentration of Compound 6 was 30 mass %. Next, ET1 was formed to a thickness of 10 nm, and then Li q and SF3-TRZ were co-evaporated from different evaporation sources to form a 20 nm thick layer. The concentrations of Liq and SF3-TRZ in the layer were 30 mass% and 70 mass%, respectively. Liq is then formed to a thickness of 2 nm, and then aluminum (Al) is formed to a thickness of 100 nm. A cathode was formed by vapor deposition onto the organic electroluminescence element, and an organic electroluminescence element was obtained. The external quantum efficiency (EQE) of the fabricated organic electroluminescence device was measured. The figure was as high as 8.9%. [ka] [Industrial Applicability]

[0127] The compound represented by the general formula (1) has good light-emitting properties. By using the compound represented by the formula (I), an excellent organic light-emitting device can be provided. High industrial applicability.

Claims

1. A compound represented by the following general formula (1): 【Chemical 1】 In the general formula (1), 1 to 4 of R 1 to R 4 are each independently represented by the following general formula (a): The remaining 0 to 3 of R 1 to R 4 and R 5 to R １２ are each independently a hydrogen atom, Deuterium atom, or hydroxyl group, halogen atom, alkyl group, alkoxy group, alkoxy group, alkylthio group, aryl group, aryloxy group, arylthio group, heteroaryl group, hetero an aryloxy group, a heteroarylthio group, an acyl group, an alkenyl group, an alkynyl group, Alkoxycarbonyl group, aryloxycarbonyl group, heteroaryloxycarbonyl group a silyl group, a silyl group, and a nitro group; or R represents a deuterium atom, a hydroxyl group, a halogen atom, an alkyl group, or a hydroxyl group. groups, alkoxy groups, alkylthio groups, aryl groups, aryloxy groups, arylthio groups, Heteroaryl group, heteroaryloxy group, heteroarylthio group, acyl group, alkene group Nyl group, alkynyl group, alkoxycarbonyl group, aryloxycarbonyl group, hetero one selected from the group consisting of an aryloxycarbonyl group, a silyl group, and a nitro group; R 6 and R 7 represent a group or a group in which two or more of them are combined, and n represents an integer of 0 to 2. R ７ , R ７ and R ８ , R ８ and R ９ , R ９ and R 10 are bonded to each other to form a ring structure. It's good.] 【Chemistry 2】 [In the general formula (a), Z 1 represents C—R 14 or N, Z 2 represents C—R 15 or N] Z 3 represents C—R 16 or N, and Z 4 represents C—R 17 or N. R 14 to Each R 17 independently represents a hydrogen atom, a deuterium atom, or an alkyl group or an aryl group; Z 5 represents one group selected from the group consisting of C and N, or a combination of two or more groups. Ar 5 represents a substituted or unsubstituted aromatic ring or a substituted or unsubstituted heteroaromatic ring; R 14 and R 15 , R 15 and R 16 , and R 16 and R 17 are bonded to each other to form a cyclic structure. It may also be formed.]

2. The compound according to claim 1, wherein the maximum emission wavelength is in the range of 420 nm to 475 nm.

3. R １ ~R ４ wherein at least two of the groups are groups represented by the general formula (a):

2. The compound according to claim 2.

4. The at least two groups represented by general formula (a) all have the same structure.

3. The compound according to claim 3.

5. R １ ~R ４ are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted aryl group, or or a group represented by general formula (a): 。

6. R １ and R ３ is a group represented by the general formula (a) The compound described in

7. R ２ is a substituted or unsubstituted aryl group or a group represented by the general formula (a) The compound according to any one of claims 1 to 6.

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

9. R １ ~R ４ at least one of the groups is a substituted or unsubstituted aryl group, The compound according to any one of claims 1 to 10.

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

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

12. A film comprising the compound according to any one of claims 1 to 9.

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

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

15. 15. The device according to claim 14, wherein the device has a layer including the compound, the layer also including a host material. The organic light-emitting element according to claim 1.

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

17. The element has a layer containing the compound, and the layer has a structure different from that of the compound. The organic light-emitting device of claim 15 , further comprising a light-emitting material that

18. 15 to 17, wherein the compound emits the maximum amount of light among the materials contained in the element.

18. The organic light-emitting device according to any one of items 17 to 17.

19. 18. The method of claim 17, wherein the amount of light emitted from the luminescent material is greater than the amount of light emitted from the compound. Organic light-emitting devices.

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

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

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