Compound, light-emitting material, and organic light-emitting device

Abstract

To provide a compound useful for an organic light-emitting element.SOLUTION: A compound represented by the general formula in the figure is provided. In the formula, R1 and R2 each represent a hydrogen atom, deuterium atom, cyano group, aryl group, or alkyl group; and R3 to R28 each represent a hydrogen atom, deuterium atom, or substituent.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a compound having good luminescence properties. The present invention also relates to a light-emitting material and an organic light-emitting device. [Background technology]

[0002] Active research into improving the luminous efficiency of organic light-emitting devices such as organic light-emitting diodes (OLEDs) It is being carried out. For example, Non-Patent Document 1 discloses 5,9-Diphenyl-5H,9H-[1,4]benzazaborino[2,3,4-kl]phena By using compounds that exhibit multiple resonance effects, such as zaborine (DABNA-1), It exhibits thermally activated delayed fluorescence due to the reverse intersystem crossing process, resulting in emission with a narrow half-width and high color purity. Such light emission can achieve high luminous efficiency. This makes them useful in display-oriented applications. In addition, Non-Patent Documents 1 and 2 report that modifying DABNA-1 increases the maximum transition rate. Adjusting energy levels such as homogeneous molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) It also promotes the fluorescence emission process and reverse intersystem crossing process that contribute to light emission, resulting in electroluminescence. It is described that the emission quantum efficiency is improved. [Prior art documents] [Non-patent literature]

[0003] [Non-Patent Document 1] Adv. Mater. 2016, 28, 2777-2781 [Non-patent document 2] Angew. Chem. Int. Ed. 2018, 57, 11316-11320 Summary of the Invention [Problem to be solved by the invention]

[0004] Various studies have been conducted on compounds that exhibit such multiple resonance effects. There are many unknowns regarding the relationship between the structure and the light-emitting properties. Therefore, it is necessary to provide materials with even slightly better light-emitting properties. Therefore, the present inventors have been conducting extensive research to develop compounds having a new ring structure. I got it. [Means for solving the problem]

[0005] As a result of intensive research, the present inventors have found that a compound that exhibits a multiple resonance effect is a specific The present invention has found that materials that satisfy these conditions are useful as materials for organic light-emitting devices. This has been proposed based on such knowledge and has the following configuration.

[0006] [1] A compound represented by the following general formula (1): [ka] [In general formula (1), R 1 and R 2 are each independently a hydrogen atom, a deuterium atom, or a cyano a group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group .R 3 ~R 28 each independently represents a hydrogen atom, a deuterium atom, or a substituent. R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 10 and R 11, R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 20 and R 21 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 26 and R 27 may be bonded to each other to form a cyclic structure. CR in general formula (1) 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , C -R 9 , C.R. 10 , C.R. 11 , C.R. 12 , C.R. 13 , C.R. 14 , C.R. 15 , CR 16 , C.R. 17 , C.R. 18 , C.R. 19 , C.R. 20 , C.R. 21 , C.R. 2 2 , C.R. 23 , C.R. 24 , C.R. 25 , C.R. 26 , C.R. 27 , C.R. 28 Few At least one of them may be substituted with N.] [2] R 3 ~R 28The compound according to [1], wherein the number of substituents is 4 or more. thing. [3] R 3 ~R 28 The compound according to [1] or [2], wherein the total number of carbon atoms is 12 or more. thing [4] R 3 ~R 28 The total number of carbon atoms is 24 or more, and one of [1] to [3] The compound described. [5] R 4 , R 7 , R 10 , R 13 , R 14 , R 17 , R 18 , R 21 , R 24 , R 2 7 The compound according to any one of [1] to [4], wherein at least one of is a substituent. [6] R 3 ~R 28 are each independently a hydrogen atom, a deuterium atom, or an alkyl group and a group consisting of one or more groups selected from the group consisting of aryl groups, The compound according to any one of [1] to [5]. [7] R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 10 and R 11 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R20 and R 21 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 26 and R 27 At least one pair of these is bonded to each other to form an aromatic ring, [1] to [6 ] The compound according to any one of the above items. [8] R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 10 and R 11 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 20 and R 21 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 26 and R 27 At least one pair of the following is bonded to each other to form a heteroaromatic ring: [1] [7] The compound according to any one of [7]. [9] The heteroaromatic ring is a furan ring, a thiophene ring, or a pyrrole ring, The nitrogen atom constituting the ring skeleton of the alkyl ring is a substituted or unsubstituted aryl group, or a substituted or unsubstituted aryl group. is substituted with an unsubstituted alkyl group.

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

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

[10] .

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

[10] .

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

[10] .

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

[10] .

[15] The organic light-emitting device according to

[0014] , wherein the device has a layer containing the compound, the layer also containing a host material.

[16] The layer containing the compound contains a delayed fluorescent material in addition to the host material, The lowest excited singlet energy of the optical material is lower than that of the host material and higher than that of the compound;

[15] The organic light-emitting device according to

[15] .

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

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

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

[0014] to

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

[19] The method according to

[17] , 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.

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

[14] to

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

[0007] The compound of the present invention exhibits excellent light-emitting properties. The compound of the present invention can be used as a material for an organic light-emitting device. The organic light-emitting device using the compound of the present invention has excellent luminous efficiency, durability, and color purity. At least one of the characteristics of the improvement is excellent. [Brief explanation of the drawings]

[0008] [Figure 1] FIG. 2 is a schematic cross-sectional view showing an example of a layer structure of an organic electroluminescence element. DETAILED DESCRIPTION OF THE INVENTION

[0009] 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 above description, H is assumed to be bonded to a carbon atom constituting the ring skeleton. The term "substituent" means an atom or group of atoms other than hydrogen and deuterium atoms. On the other hand, the term "substituted or unsubstituted" refers to a group in which a hydrogen atom is replaced with a deuterium atom or a substituent. This means that the ion may be replaced.

[0010] [Compound represented by general formula (1)] The compound of the present invention is a compound represented by the following general formula (1).

[0011] [ka]

[0012] In general formula (1), R 1 and R 2 are each independently a hydrogen atom, a deuterium atom, or a cyano a group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted alkyl group .R 1 and R 2 each independently represents a hydrogen atom, a deuterium atom, a cyano group, or an aryl group; and alkyl groups, It is preferable that the hydroxyl group is a hydrogen atom, a deuterium atom, a cyano group, a cyano group or an alkyl group. an aryl group (e.g., a phenyl group, a cyanophenyl group) optionally substituted with a phenyl group, is more preferably an alkyl group which may be substituted with a cyano group or an aryl group. In one aspect of the present invention, R 1 and R 2 are each independently a hydrogen atom, a deuterium atom, or is a cyano group. In one aspect of the invention, R 1 and R 2 are each independently a hydrogen atom or It is a deuterium atom.

[0013] In general formula (1), R 3 ~R 28 are each independently a hydrogen atom, a deuterium atom or a substituted Represents a group. R 3 ~R 28 The substituents that can be taken by may be selected from, for example, the substituent group A. It may be selected from the group B of substituents, or may be selected from the group C of substituents, or may be selected from the group D of substituents. or may be selected from the substituent group E. In one aspect of the present invention, R 3 ~R 28 The substituent that can be taken by the group is a substituted or unsubstituted alkyl group. So, R 3 ~R28 The substituent that can be taken by is a substituted or unsubstituted aryl group. In one embodiment, R 1 ~R 26 The substituents that can be taken are substituted or unsubstituted groups having 1 to 10 carbon atoms. It is an alkyl group or a substituted or unsubstituted aryl group having 6 to 15 carbon atoms. In one aspect of the present invention, R 3 ~R 28 At least one of the groups is a substituted or unsubstituted alkyl group. group, preferably R 4 ~R 27 , more preferably R 4 ~R 14 , R 17 ~R 27 few At least one of R is a substituted or unsubstituted alkyl group. 5 ~R 26 At least one of R is a substituted or unsubstituted aryl group, and preferably R 4 ~R 2 7 , more preferably R 4 ~R 14 , R 17 ~R 27 At least one of the following is replaced or omitted. In one aspect of the invention, R 4 , R 7 , R 10 , R 13 , R 14 , R 17 , R 18 , R 21 , R 24 , R 27 At least one of the substituents has 1 to 10 carbon atoms. or an unsubstituted alkyl group, or a substituted or unsubstituted aryl group having 6 to 15 carbon atoms. For example, an unsubstituted alkyl group having 1 to 6 carbon atoms or an unsubstituted aryl group having 6 to 10 carbon atoms. In one aspect of the present invention, R 4 , R7 , R 10 , R 13 , R 14 , R 17 , R 1 8 , R 21 , R 24 , R 27 are each independently a hydrogen atom, a deuterium atom, or an alkyl group. and aryl groups, Yes, other R 3 ~R 28 are each independently a hydrogen atom or a deuterium atom. The "alkyl group" referred to in this specification may be linear, branched, or cyclic. In addition, two or more of the straight chain portion, cyclic portion and branched portion may be mixed. The number of carbon atoms can be, for example, 1 or more, 2 or more, or 4 or more. The alkyl group may be 20 or less, 10 or less, 6 or less, or 4 or less. methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group group, 2-ethylhexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group Octyl group, n-nonyl group, isononyl group, n-decanyl group, isodecanyl group, cyclopentyl group Examples of the alkyl group include cyclohexyl, cyclohexyl, and cycloheptyl. Some or all of the atoms may be substituted with deuterium atoms. may be selected from, for example, Substituent Group A or Substituent Group B. , may be selected from the substituent group C, may be selected from the substituent group D, or may be selected from the substituent It may be selected from group E. The "aryl group" referred to in this specification 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. Specific examples of the ring include a benzene ring, a naphthalene ring, and a hydroxyl group. Examples include a phthalene ring, an anthracene ring, a phenanthrene ring, and a triphenylene ring. Specific examples of the aryl group include a substituted or unsubstituted phenyl group, a substituted or unsubstituted and substituted or unsubstituted naphthalen-2-yl groups. Some or all of the hydrogen atoms of the aryl group may be substituted with deuterium atoms. The substituent of the aryl group may be selected from, for example, the substituent group A, or may be selected from the substituent group B. It may be selected from the substituent group B, or from the substituent group C, or from the substituent group D. or may be selected from the substituent group E, and preferably an alkyl group having 1 to 6 carbon atoms. It is an alkyl group. In the following, R 3 ~R 28 Specific examples of the substituents that can be adopted by the present invention are shown below. The substituents that can be used are not to be construed as being limited by the following specific examples. In the specific examples, * indicates the bond position. In addition, methyl groups are omitted except for N1. For example, N2 is an ethyl group, N3 is an isopropyl group, and N4 is a tert-butyl group. [ka]

[0014] R 3 ~R 28 The number of substituents may be 0 or 1 or more. For example, it may be 2 or more, 4 or more, or 6 or more. It may also be 18 or less, 12 or less, or 6 or less. In one embodiment of the present invention, the number of substituents is 2 to 10. In another embodiment of the present invention, the number of substituents is 2 to 6. do. In one aspect of the present invention, R 4 , R 7 , R 10 , R 13 , R 14 , R 17 , R 18 , R 21 , R 24 , R 27 At least one of the groups is a substituent, for example, even if 2 to 6 of the groups are substituents, In one embodiment of the present invention, R 7 and R 13 are the same substituents In one aspect of the present invention, R 7 , R 13 , R 18 and R 24 are the same substituents. In one embodiment, R 10 and R 13 are the same substituents. In one aspect of the invention, R 10 , R 1 3 , R 18 and R 21 are the same substituents. In one aspect of the present invention, R 3 , R 5 , R 6 , R 8 , R 9 , R 11 , R 12 , R 15 , R 1 6 , R 19 , R 20 , R 22 , R 23 , R 25 , R 26 , R 28 are each independently a hydrogen atom or or a deuterium atom. In one aspect of the present invention, R 3 , R 4 , R 5 , R 6 , R 8 , R 9 , R 11 , R 12 , R 15 , R 16 , R 19 , R 20 , R 22 , R 23 , R 25 , R 26 , R 27 , R 28 are each independently a hydrogen atom or a deuterium atom.

[0015] R 3 ~R 28 The total number of carbon atoms in the formula (I) may be 0 or 1 or more. For example, you can select from a range of 6 or more, or a range of 15 or more, or a range of 24 or more. The upper limit may be selected from a range of 100 or less, or from a range of 50 or less. In one aspect of the present invention, the number of ions may be selected from within the range of 1 to 30. , R 3 ~R 28 The total number of carbon atoms is 16 to 100. For example, R 7 , R 13 , R 18 , R 2 4 is a tert-butyl group, and other R 3 ~R 28 is a hydrogen atom, R 3 ~R 2 8 The total number of carbon atoms in R is 16. 3 ~R 28 The total number of carbon atoms is 24 or more 100. For example, R 7 , R 13 , R 18 , R24 is a phenyl group, and other R 3 ~R 28 is a hydrogen atom, R 3 ~R 28 The total number of carbon atoms is 24. In one aspect of the present invention, R 3 ~R 9 and R 22 ~R 28 The total number of carbon atoms in R 10 ~R 2 1 In one aspect of the present invention, the total number of carbon atoms in R 12 ~R 19 The total number of carbon atoms in R 1 0 , R 11 , R 20 , R 21 The total number of carbon atoms is equal to or greater than the above.

[0016] In general formula (1), R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 10 and R 11 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 20 and R 21 , R 22 and R 23 , R 23 and R 24 , R 24 and R 25 , R 26 and R 27may be bonded to each other to form a cyclic structure. The cyclic structure is any one of an aromatic ring, a heteroaromatic ring, an aliphatic hydrocarbon ring, and an aliphatic heterocyclic ring. It may be a ring formed by condensing these rings. Aromatic rings and heteroaromatic rings are preferred. The aromatic ring may be a substituted or unsubstituted benzene ring. may be further fused with another benzene ring, or may be fused with a heterocyclic ring such as a pyridine ring. The heteroaromatic ring means a ring that contains a heteroatom as a ring skeleton-constituting atom and exhibits aromaticity. However, 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 furan ring, a thiophene ring, or the like can be used as the heteroaromatic ring. In one embodiment of the present invention, R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 One or two of the groups bond together to form a ring structure. In one aspect of the present invention, R 10 and R 11 are bonded to each other to form a ring structure In one aspect of the present invention, R 12 and R 13 , R 13 and R 14 , R 14 and R 15 One of the pairs In one embodiment of the present invention, R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 One or two pairs of R 22 and R23 , R 23 and R 24 , R 24 and R 25 , R 26 and R 27 One or two of the pairs are bonded to form a ring In one aspect of the present invention, R 10 and R 11 , R 20 and R 21 are respectively In one embodiment of the present invention, R 12 and R 13 , R 13 and R 14 , R 14 and R 15 One or two pairs of R 16 and R 17 , R 17 and R 18 , R 18 and R 19 One or two of these pairs are bonded to each other to form a ring structure.

[0017] In one aspect of the present invention, R 4 and R 5 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 10 and R 11 , R 12 and R 13 , R 13 and R 14 , R 14 and R 15 , R 16 and R 17 , R 17 and R 18 , R 18 and R 19 , R 20 and R 21 , R 22 and R 23 , R 23 and R24 , R 24 and R 25 , R 26 and R 27 At least one pair of these is bonded to each other to form a substituted or unsubstituted The furan ring of benzofuran, the thiophene ring of substituted or unsubstituted benzothiophene, or pyrrole ring of unsubstituted indole, cyclopentene of substituted or unsubstituted indene The silane ring is a substituted or unsubstituted silane ring. Benzofuran, benzothiophene, indole, indene, and silaindene are 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. It may be substituted with a substituent selected from the substituent group D, or may be substituted with a substituent selected from the substituent group D. The pyrrole ring of the indole may be substituted with a substituent selected from Group E. The nitrogen atom is preferably bonded to a substituted or unsubstituted aryl group, and the substituent Examples of the substituent include a substituent selected from any one of the substituent groups A to E. The carbon atoms constituting the methylene group of the cyclopentadiene ring of indene and the silane The silicon atom constituting the silole ring of indene is substituted with a substituent selected from the substituent group E. In this embodiment, the ring structure is formed to form the ring structure represented by the general formula (1) Among them, there are benzofuran-fused carbazole structures, benzothiophene-fused carbazole structures, and Indole-fused carbazole structure, indene-fused carbazole structure, silaindene-fused carbazole structure A bazole structure is formed.

[0018] The benzofuran-fused carbazole structure has only one benzofuran ring fused at the 2- and 3-positions. It may be a fused benzofuran ring or a fused benzofuran ring. The benzofuran ring may be fused at the 2- and 3-positions and other rings may also be fused. The condensed ring may be an aromatic hydrocarbon ring, an aromatic heterocyclic ring, an aliphatic hydrocarbon ring, an aliphatic heterocyclic ring, or an An example of an aromatic hydrocarbon ring is a benzene ring. Examples of aromatic heterocycles include pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, tricyclic ring, and the like. Examples of the ring include an azine ring, a pyrrole ring, a pyrazole ring, and an imidazole ring. Examples of the hydrogen ring include a cyclopentane ring, a cyclohexane ring, and a cycloheptane ring. Examples of the aliphatic heterocyclic ring include a piperidine ring, a pyrrolidine ring, and an imidazoline ring. Specific examples of the fused ring constituting the aromatic hydrocarbon ring include a naphthalene ring, Examples include an anthracene ring, a phenanthrene ring, a pyran ring, and a tetracene ring. Specific examples of the fused ring containing a hetero atom include an indole ring, an isoindole ring, a benzoindole ring, and the like. an imidazole ring, a benzotriazole ring, a quinoline ring, an isoquinoline ring, a quinazoline ring, Examples include a quinoxaline ring and a cinnoline ring. In the present invention, the benzofuran-fused carbazole structure is a substituted or unsubstituted benzofuran. The furo[2,3-a]carbazole structure can be used. A substituted benzofuro[3,2-a]carbazole structure can also be used. Alternatively, an unsubstituted benzofuro[2,3-b]carbazole structure can be used. In addition, substituted or unsubstituted benzofuro[3,2-b]carbazole structures can also be used. In addition, the substituted or unsubstituted benzofuro[2,3-c]carbazole structure is used. In addition, substituted or unsubstituted benzofuro[3,2-c]carbazoles can also be used. The structure can also be adopted. The preferred benzofuran-fused carbazole structure has only one benzofuran ring at the 2- and 3-positions. It is a carbazole structure in which the ring is condensed and no other rings are condensed. The hydrogen atoms in the following structures may be substituted. For example, Some of the hydrogen atoms in the following structure have been replaced with deuterium atoms, and A preferred example is one in which all of the atoms are substituted with deuterium atoms. * indicates a bonding position. Although only the 8th and 9th positions of the carbazole ring are shown, the carbazole ring incorporated in general formula (1) Depending on the position of the benzol structure, it may also be bonded at the 7th position. If it is also bonded at the 8th position, Among the following specific examples, those fused at the 6-position cannot be adopted. [ka]

[0019] Two benzofuran rings are fused at the 2- and 3-positions, and there is no other ring fused to the carbazole structure. Specifically, it is a group having any one of the following structures, and the hydrogen atoms in the following structures are preferably Atoms may be substituted. For example, some of the hydrogen atoms in the following structure have been substituted with deuterium atoms: and those in which all hydrogen atoms in the following structure are replaced with deuterium atoms. Unsubstituted alkyl groups can also be preferably used. [ka]

[0020] The benzothiophene-fused carbazole structure has only one benzothiophene ring at the 2- and 3-positions. It may be a fused one, or two or more benzothiophene rings may be fused one. In addition, a compound in which the benzothiophene ring is fused at the 2- and 3-positions and other rings are fused thereto may also be used. For details and specific examples of the fused rings, see the above benzofuran-fused rings. Please refer to the explanation and specific examples of the fused rings in the explanation of the benzol structure. In the benzothiophene-fused carbazole structure, substituted or unsubstituted benzothiophenes are used. The 2,3-a-carbazole structure can be used. The benzothieno[3,2-a]carbazole structure can also be used. Alternatively, an unsubstituted benzothieno[2,3-b]carbazole structure can be employed. In addition, by adopting a substituted or unsubstituted benzothieno[3,2-b]carbazole structure, In addition, substituted or unsubstituted benzothieno[2,3-c]carbazole structures can be used. It is also possible to use substituted or unsubstituted benzothieno[3,2-c]carbazole. A bazoline structure may also be employed. A preferred benzothiophene-fused carbazole structure is one in which the benzothiophene ring is at the 2- and 3-positions. It is a carbazole structure with only one fused ring and no other fused rings. The group has any one of the following structures, and the hydrogen atoms in the following structures may be substituted. For example, some of the hydrogen atoms in the following structure are replaced with deuterium atoms, and A preferred example is one in which all of the hydrogen atoms are substituted with deuterium atoms. Unsubstituted groups can also be preferably used. [ka]

[0021] Two benzothiophene rings are fused at the 2- and 3-positions, and no other rings are fused. Specifically, it is a group having any one of the following structures, The hydrogen atoms may be substituted. For example, some of the hydrogen atoms in the following structure are replaced with deuterium atoms. Substituted or all hydrogen atoms in the following structures are replaced with deuterium atoms Preferred examples include the following. Unsubstituted groups can also be preferably used. [ka]

[0022] The indole-fused carbazole structure has only one indole ring fused at the 2- and 3-positions. Alternatively, two or more indole rings may be fused together. The 2- and 3-positions of the dole ring may be fused with other rings. For details and specific examples of the ring, see the description of the benzofuran-fused carbazole structure above. In the present invention, the indole-fused carboxylate ring is preferably an indole-fused carboxylate ring. The carbazole structure is a substituted or unsubstituted indolo[2,3-a]carbazole structure. Substituted or unsubstituted indolo[3,2-a]carbazoles can also be used. In addition, a substituted or unsubstituted indolo[2,3-b]carbonyl structure can be used. A rubazoline structure can also be used. -b]carbazole structure can also be used. [2,3-c]carbazole structures can also be used. An indolo[3,2-c]carbazole structure can also be employed. The preferred indole-fused carbazole structure has only one indole ring fused at the 2- and 3-positions. In addition, it is a carbazole structure with no other rings condensed. Specifically, it is one of the following: In the following structure, R represents a hydrogen atom, a deuterium atom, or a substituent (preferably (R represents a substituent). In addition, the hydrogen atoms in the following structures may be substituted. For example, , some of the hydrogen atoms in the following structure are replaced with deuterium atoms, and A preferred example is one in which all atoms are substituted with deuterium atoms. can also be preferably used. [ka]

[0023] The indene-fused carbazole structure has only one indene ring fused at the 2- and 3-positions. Alternatively, two or more indene rings may be condensed. are fused at the 2- and 3-positions, and other rings may also be fused. For details and specific examples, see the fused benzofurans in the description of the benzofuran-fused carbazole structure above. In the present invention, when referring to an indene ring, This explanation is based on the assumption that 1H-indene exists (there is a double bond between the 2nd and 3rd positions). When specifying indenocarbazole, the nomenclature is indeno[2,3 The term is called indeno[3,2-x]carbazole or indeno[3,2-x]carbazole (where x is a, b, or In the present invention, the indene-fused carbazole structure is a substituted or unsubstituted indene. The deno[2,3-a]carbazole structure can be used. A substituted indeno[3,2-a]carbazole structure can also be employed. Alternatively, an unsubstituted indeno[2,3-b]carbazole structure may be employed. Substituted or unsubstituted indeno[3,2-b]carbazole structures can also be employed. In addition, by adopting a substituted or unsubstituted indeno[2,3-c]carbazole structure, In addition, substituted or unsubstituted indeno[3,2-c]carbazole structures are also available. You can also do this. A preferred indene-fused carbazole structure has only one indene ring fused at the 2- and 3-positions, In addition, the ring is not condensed and it is a carbazole structure. Specifically, it is one of the following structures. The hydrogen atoms in the following structure may be substituted. For example, the following structure Some of the hydrogen atoms in the structure are replaced with deuterium atoms, and all of the hydrogen atoms in the structure below are replaced with deuterium atoms. Preferred examples include those in which the alkyl group is substituted with a deuterium atom. can also be preferably employed. [ka]

[0024] The silaindene-fused carbazole structure has only one silaindene ring fused at the 2- and 3-positions. It may be a fused silainden ring, or two or more silainden rings may be fused silainden rings. The silaindene ring may be fused at the 2- and 3-positions and other rings may also be fused. For details and examples of fused rings, see the above description of the benzofuran-fused carbazole structure. The explanation and specific examples of fused rings in the present invention can be referred to. When referring to the silane ring, we will assume that it is 1H-silyladene (there is a double bond between the 2nd and 3rd positions). On the other hand, when specifying silaindenocarbazole, the IUPAC nomenclature According to the method, silaindeno[2,3-x]carbazole or silaindeno[3,2-x ]carbazole (x is a, b or c). In the present invention, silaindene-fused carbazo As the carbazole structure, substituted or unsubstituted silaindeno[2,3-a]carbazole structure is used. Substituted or unsubstituted silaindeno[3,2-a]carba A sol structure can also be adopted. Also, substituted or unsubstituted silaindeno[2,3 -b] carbazole structure can also be adopted. A deno[3,2-b]carbazole structure can also be used. A substituted silaindeno[2,3-c]carbazole structure can also be adopted. Alternatively, an unsubstituted silaindeno[3,2-c]carbazole structure can be adopted. . The preferred silaindene-fused carbazole structure has only one silaindene ring at the 2- and 3-positions. It is a carbazole structure in which the ring is condensed and no other rings are condensed. In the following structure, R and R' are each independently a hydrogen atom, a deuterium atom, or a represents an atom or a substituent (preferably R and R' are substituents). Also, hydrogen in the following structure Atoms may be substituted. For example, some of the hydrogen atoms in the following structure have been substituted with deuterium atoms: and those in which all hydrogen atoms in the following structure are replaced with deuterium atoms. Preferred examples include unsubstituted groups. R' may be the same or different, and may be bonded to each other to form a cyclic structure. stomach. [ka]

[0025] Benzofuran-fused carbazole structure and benzothiophene-fused carbazole structure that can be employed in general formula (1) Carbazole structure, indole-fused carbazole structure, indene-fused carbazole structure, The silaindene-fused carbazole structure may be substituted. If substituted, it may be substituted with a deuterium atom or with another atom. The substituent may be an alkyl group, an alkenyl group, or the like. , an aryl group, a heteroaryl group, an alkoxy group, an alkylthio group, an aryloxy group, Examples include an arylthio group, a heteroaryloxy group, a heteroarylthio group, and a cyano group. These substituents may be further substituted with other substituents. For example, A form substituted with a hydrogen atom, an alkyl group, an aryl group, an alkoxy group, or an alkylthio group. Examples include:

[0026] CR in general formula (1) 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C.R. 8 , C -R 9 , C.R. 10 , C.R. 11 , C.R. 12 , C.R. 13, C.R. 14 , C.R. 15 , CR 16 , C.R. 17 , C.R. 18 , C.R. 19 , C.R. 20 , C.R. 21 , C.R. 2 2 , C.R. 23 , C.R. 24 , C.R. 25 , C.R. 26 , C.R. 27 , C.R. 28 Few At least one of them may be substituted with N. When N is substituted, the number of substitutions is preferably 1 to 6, for example, any of 4 to 6. It may be set to 1, 2, 3, or 4. For example, CR 3 , C.R. 4 , C- R 5 , C.R. 6 , C.R. 7 , C.R. 8 , C.R. 9 0 to 2 of these are replaced by N For example, CR 10 , C.R. 11 0 to 1 of these may be substituted with N. For example, CR 12 , C.R. 13 , C.R. 14 , C.R. 15 0 to 1 of them are placed in N. For example, CR 16 , C.R. 17 , C.R. 18 , C.R. 19 Of may be substituted with N. For example, CR 20 , C.R. 21 0 of One may be substituted with N. For example, CR 22 , C.R. 23 , C.R. 24, C- R 25 , C.R. 26 , C.R. 27 , C.R. 28 Even if 0 to 2 of In one aspect of the present invention, CR 3 , C.R. 4 , C.R. 5 , C.R. 6 , C.R. 7 , C- R 8 , C.R. 9 In one embodiment of the present invention, one or two of C -R 10 , C.R. 11 In one embodiment of the present invention, one of CR 12 , C.R. 13 , C.R. 14 , C.R. 15 wherein one of the groups is substituted with N. In one embodiment, CR 16 , C.R. 17 , C.R. 18 , C.R. 19 One of them is placed in N. In one aspect of the present invention, CR 20 , C.R. 21 One of them is replaced by N. In one aspect of the present invention, CR 22 , C.R. 23 , C.R. 24 , C.R. 25 , C -R 26 , C.R. 27 , C.R. 28 One or two of the groups are substituted with N. In one embodiment, 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. 14 , C.R. 15 , C -R 16 , C.R. 17 , C.R. 18 , C.R. 19 , C.R. 20 , C.R. 21 , C.R. 22 , C.R. 23 , C.R. 24 , C.R. 25 , C.R. 26 , C.R. 27 , C.R. 28 Either is not replaced by N.

[0027] The compound represented by the general formula (1) preferably does not contain a metal atom. The group atoms do not include boron atoms. For example, the compound represented by general formula (1) is It consists of hydrogen, deuterium, nitrogen, oxygen, sulfur and boron atoms. For example, a compound having atoms selected from the group consisting of the general formula (1) As a compound represented by the formula: A compound consisting of atoms selected from the group consisting of boron atoms can be selected. For example, the compound represented by the general formula (1) may contain carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms, a compound comprising atoms selected from the group consisting of sulfur atoms and boron atoms; For example, the compound represented by the general formula (1) can be a compound containing carbon atoms, hydrogen atoms, heavy water, A compound consisting of atoms selected from the group consisting of hydrogen atoms, nitrogen atoms, and boron atoms is selected. For example, the compound represented by the general formula (1) can be a compound containing carbon atoms, hydrogen atoms, , nitrogen atoms, oxygen atoms, sulfur atoms, and boron atoms. For example, the compound represented by the general formula (1) can be selected from the group consisting of carbon A compound consisting of atoms selected from the group consisting of hydrogen atoms, nitrogen atoms, and boron atoms. You can select things.

[0028] 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 alkyl 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) means one group 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, when "substituted" or "substituted or unsubstituted" is used, 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.

[0029] In one embodiment of the present invention, the compound represented by general formula (1) is a compound having a linear symmetric structure. In one embodiment of the present invention, the compound represented by general formula (1) is selected from the group consisting of a compound having an asymmetric structure and a compound represented by general formula (1). Select the compound you want to analyze.

[0030] In one aspect of the present invention, R in general formula (1)3 ~R 28 are each independently a hydrogen atom or a deuterium atom Or a group having a Hammett's σp value of -0.2 or more. In one embodiment of the present invention, R 3 ~R 28 are each independently a hydrogen atom, a deuterium atom, or a group having a positive Hammett σp value. In one aspect of the present invention, R in general formula (1) 3 ~R 28 are each independently a hydrogen atom, a deuterium atom In one embodiment of the present invention, the compound represented by the general formula (1) is a group having a Hammett's σp value of 0.2 or less. R 3 ~R 28 are each independently a hydrogen atom, a deuterium atom, or a group having a negative Hammett σp value. In one aspect of the present invention, R in general formula (1) 3 ~R 28 are each independently a hydrogen atom, a deuterium atom The group has a Hammett σp value of -0.2 to 0.2.

[0031] The compound represented by the general formula (1) preferably has, for example, any one of the following skeleton structures: X in the skeleton structure is O, S, N(R 31 ), C(R 32 )(R 33 ), Si(R 34 )(R 35 ) and R here 31 is a substituted or unsubstituted aryl R represents a group, or a substituted or unsubstituted alkyl group. 32 ~R 35 are each independently hydrogen atoms It represents a substituted or unsubstituted alkyl group, a deuterium atom, or at least one of the following skeletons: The hydrogen atoms of the rings may be substituted with deuterium atoms or substituents. For details of the substituents, see the above R 1 ~R 28 The theory of substituents in the description of You can refer to the explanation.

[0032] [ka] JPEG0007784080000012.jpg140170

[0033] Specific examples of the compound represented by formula (1) are given below. The compounds represented by general formula (1) that can be used in the present invention are not limited to these specific examples. In the following specific examples, R in each general formula n (n is an integer The specific structure is specified by specifying the number of elements and X. When specifying each structure, R n is a substituent, the substituent is specified. n When is a hydrogen atom is R n For example, in compound 1a, R 4 , R 7 , R 10 , R 14 is a hydrogen atom, and Ph represents a phenyl group.

[0034] [ka] JPEG0007784080000014.jpg255156JPEG0007784080000015.jpg130161JPEG0007784080000016.jpg227170JPEG0007784080000017.jpg225170 JPEG0007784080000018.jpg220170JPEG0007784080000019.jpg225170JPEG0007784080000020.jpg234170JPEG0007784080000021.jpg234170

[0035] In the above compounds 1a to 20I, all hydrogen atoms present in the molecule are replaced with deuterium atoms. The converted compounds are disclosed herein as compounds 1a(D) to 20I(D), respectively.

[0036] 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.

[0037] 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.

[0038] 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]

[0039] 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.

[0040] Specific structural examples of the repeating unit include structures represented by the following formulas. [ka]

[0041] 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]

[0042] 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.

[0043] 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 in the UV region and the visible spectrum, blue, green, yellow, orange, and red Color region (e.g., about 420 nm to about 500 nm, about 500 nm to about 600 nm, or about 60 It can emit light in the wavelength range of 1000 nm to about 700 nm or in the near-infrared region. In one embodiment of the present disclosure, the compound represented by general formula (1) is When excited by It can emit light at wavelengths from about 650 nm to about 780 nm. In one embodiment of the present disclosure, the compound represented by general formula (1) is When excited by It can emit light at wavelengths ranging from about 620 nm to about 590 nm, about 570 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 When excited by It can emit light at wavelengths of about 475 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, the compound represented by general formula (1) is Emitting light in the infrared spectral region (e.g., 780 nm to 2 μm) 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) For example, a CMOS (complementary metal oxide semiconductor) device using the compound represented by general formula (1) can be fabricated. In one embodiment of the present disclosure, a compound having the general formula The compound represented by (1) is used to produce an organic electroluminescence element or a solid-state imaging element (e.g. It is possible to fabricate organic optical devices such as CMOS image sensors.

[0044] 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.

[0045] [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, it can be synthesized by using a ring-closing reaction or a substitution reaction. For example, 2-(carbazole-9)-substituted or unsubstituted at the 4- and 6-positions can be used. 1,3-Dibromobenzene substituted with n-bromo- After reacting with diethyllithium, boron tribromide was added, and then N-ethyldiisopropyl It can be synthesized by adding an amine and stirring to cause cyclization. For details of the reaction conditions, please refer to the synthesis examples described below.

[0046] [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.

[0047] [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.

[0048] [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. An example of an electroluminescent device is shown in FIG.

[0049] 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.

[0050] 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:

[0051] [ka] JPEG0007784080000026.jpg222166JPEG0007784080000027.jpg255169

[0052] 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.

[0053] 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.

[0054] 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.

[0055] In the following, each component of the organic electroluminescence element and each layer other than the light-emitting layer We will explain about this.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] 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 hole injection materials are listed below.

[0060] [ka]

[0061] Next, preferred examples of compounds that can be used as the electron injection material will be listed. [ka]

[0062] 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

[0063] 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.

[0064] [ka]

[0065] 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.

[0066] [ka]

[0067] 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.

[0068] 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.

[0069] [ka]

[0070] 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.

[0071] [ka]

[0072] Furthermore, examples of compounds that can be added to each organic layer include: It is conceivable to add it as a material.

[0073] [ka]

[0074] 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.

[0075] 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.

[0076] 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.

[0077] 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.

[0078] 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

[0079] 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.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] 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]

[0085] 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).

[0086] (Synthesis Example 1) Synthesis of Compound 1 [ka]

[0087] Under a nitrogen atmosphere, 2-bromo-9H-carbazole (2.46 g, 10.0 mmol), Rubazol (1.67 g, 10.0 mmol), tris(dibenzylideneacetone)dipa Radium(0) (0.915 g, 1.00 mmol) and tri-tert-butylphosphonium A solution of tetrafluoroborate (0.580 g, 4.00 mmol) in tetrahydrofuran was Lithium bis(trimethylsilyl)amide (1.0 mol / L tetrahydrofuran) was added to the solution (30 mL). A solution of 25 mL of 25.0 mmol of toluene was added and the mixture was stirred at 65°C for 24 hours. The mixture was filtered through Celite, and the solvent in the filtrate was evaporated. The mixture was purified by filtration (toluene:hexane = 4:6) to give intermediate A (0.560 g) as a white solid. The compound was obtained in an amount of 1.68 mmol (18% yield). 1 HNMR (400 Hz, DMSO-d6, d): 11.50 (s, 1H), 8.39 (d, J = 8.0 Hz, 1H), 8.29-8.26 (m, 2H), 8.23 ​​(d, J = 7.6 Hz, 1H), 7.69-7.68 (m, 1H), 7.57 (d, J = 8.0 Hz, 1H), 7.48-7.42 (m, 5H), 7.36 (dd, J = 8.0 Hz, 2.0 Hz, 1H), 7.33-7.28 (m, 2H), 7.26-7. 23 (m, 1H) MS (ASAP): 333.16 (M+H + ). Calcd for. C 24 H 16 N2: 332.13

[0088] [ka]

[0089] Under a nitrogen atmosphere, 1,5-dibromo-2,4-difluorobenzene (2.00 g, 7.36 mmol), intermediate A (6.12 g, 18.4 mmol) and cesium carbonate (4.07 g, 29.4 mmol) in N,N-dimethylformamide (DMF solution, 80 mL) Stir at 40°C for 16 hours. Cool the mixture to room temperature, add water and filter. The product was purified by gel column chromatography and recrystallization to give a white solid.

[0090] [ka]

[0091] Under a nitrogen atmosphere, a solution of intermediate B (1.00 g, 1.12 mmol) in toluene (100 mL ) at -30°C, n-BuLi (1.6 mol / L hexane solution, 2.1 mL, 3.36 m mol) was added and stirred at 50°C for 30 minutes. The reaction mixture was cooled to -30°C and phosphate tribromide was added. Add iodine (1.40 g, 5.60 mmol) and stir at room temperature for 30 minutes. -Ethyldiisopropylamine (0.724 g, 5.60 mmol) was added and the mixture was heated at 120°C. The mixture was stirred for 16 hours, the reaction mixture was cooled to room temperature, and the solvent was evaporated. Purification by column chromatography gives compound 1 as a yellow solid.

[0092] (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 1 and phosphatase were synthesized under conditions below Pa. The compound 1 was evaporated from a different evaporation source, and a thin film with a concentration of 20 wt% was formed on the substrate. This is the thin film of Example 1. The thin film of Example 1 has excellent properties.

[0093] (Example 2) Fabrication and evaluation of organic electroluminescence device Glass with an anode made of 100 nm thick indium tin oxide (ITO) Each thin film was deposited on the substrate by vacuum deposition at a vacuum of 1 x 10 -6 First, ITO A first hole injection layer made of a first hole injection material is formed on the first hole injection layer, and a second hole injection layer made of a second hole injection material is formed on the first hole injection layer. a second hole injection layer made of a hole transport material is formed thereon, and a hole transport layer made of a hole transport material is formed thereon; An electron blocking layer made of an electron blocking material is formed thereon. The fluorescent material and Compound 1 were co-deposited from different deposition sources. The host material concentration was 69 wt.%, and the delayed fluorescent material A light-emitting layer is formed with a concentration of the optical material of 30% by weight and a concentration of Compound 1 of 1% by weight. A hole blocking layer made of a blocking material is formed, an electron transport layer is formed thereon, and an electron By the above procedure, the organic electroluminescence element of Example 2 was fabricated. The organic electroluminescence device of Example 2 has excellent characteristics.

[0094] Instead of Compound 1, a compound other than Compound 1 represented by the general formula (1) was used to prepare Example 1. A thin film and an organic electroluminescence element were prepared by the same procedure as in Example 2. It is possible. [Explanation of symbols]

[0095] 1 Base material 2 Anode 3. Hole injection layer 4. Hole transport layer 5. Light-emitting layer 6 Electron transport layer 7 Cathode

Claims

1. A compound represented by the following general formula (1): 【Chemistry 1】 [In general formula (1), R 1 to R 28 each independently represent a hydrogen atom or a deuterium atom] 。］

2. The compound according to claim 1, which has an axisymmetric structure.

3. A light-emitting material comprising the compound according to claim 1 or 2.

4. A membrane comprising a compound according to claim 1 or 2.

5. An organic semiconductor device comprising the compound according to claim 1 or 2.

6. An organic light-emitting device comprising the compound according to claim 1 or 2.

7. 10. The method of claim 6, wherein the device has a layer containing the compound, the layer also containing a host material. The organic light-emitting device described above.

8. The layer containing the compound contains a delayed fluorescent material in addition to the host material, and 8. The compound according to claim 7, wherein the lowest excited singlet energy is lower than that of the host material and higher than that of the compound. The organic light-emitting element according to claim 1.

9. 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 6 , further comprising a light-emitting material.

10. Claims 6 to 8: The compound has the largest amount of light emission among the materials contained in the element.

10. The organic light-emitting element according to any one of claims 1 to 9.

11. The compound according to claim 9, wherein the amount of light emitted from the luminescent material is greater than the amount of light emitted from the compound. Light emitting element.

12. The organic light-emitting device according to any one of claims 6 to 11, which emits delayed fluorescence.

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