Organic compound and application thereof

Abstract

The invention provides an organic compound and application thereof. The compound has a structure as shown in a formula (1), R1 is a structure as shown in a formula a, and Ar1 is a structure as shown in a formula b. The compound provided by the invention has a narrow fluorescence emission spectrum and high quantum efficiency, and can effectively improve the luminous efficiency and service life of an organic electroluminescent device when being applied to the organic electroluminescent device.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescent materials technology, specifically relating to a compound and its applications, and organic electroluminescent devices containing the same. Background Technology

[0002] In recent years, electroluminescent devices based on organic materials (such as organic light-emitting diodes, OLEDs) have become increasingly popular. Compared with electroluminescent devices based on inorganic materials, the inherent flexibility of organic materials makes them ideal for manufacturing flexible, thin electroluminescent devices. This allows for the design and production of aesthetically pleasing and stylish screens, displays, and lighting equipment, offering unparalleled advantages over inorganic materials. Currently, OLED-based screens and displays already exhibit good efficiency and lifespan; however, achieving long lifespan, high efficiency, and high color purity simultaneously remains a research challenge for OLED devices.

[0003] With the rapid development of information technology, display technology faces higher demands. For example, to meet the BT-2020 color gamut standard for 4K and 8K image signals, the CIEy for green light is 0.797, significantly increasing color gamut coverage. Currently, using luminescent materials with narrow half-width emission spectra is one of the important means to achieve high color purity, especially in commercially available OLED materials. Green luminescent materials, which use phosphorescent materials with wide half-widths and strong shoulder peaks at long wavelengths, struggle to simultaneously meet the requirements of high efficiency and excellent color purity. In recent years, scientists have developed thermally activated delayed fluorescence (TADF) materials that possess both 100% theoretical exciton utilization and a narrow emission spectrum. Using these materials as OLED luminescent materials holds promise for achieving the high color purity requirement of BT-2020 while maintaining high efficiency. However, these materials suffer from severe efficiency roll-off at high brightness and have short device lifetimes, far from meeting the standards for mass production and use. To address this issue, scientists have proposed a superfluorescence strategy. This involves transferring the excited-state energy of TADF or phosphorescent materials to narrow-spectrum fluorescent materials for luminescence. This achieves both theoretically 100% exciton utilization and a narrow emission spectrum, potentially leading to OLED devices with good efficiency, long lifetime, and high color purity. Furthermore, phosphorescent materials are typically based on transition metals such as iridium and platinum. Due to their generally low abundance, they are among the most expensive OLED materials. Therefore, reducing the amount of phosphorescent material used is crucial for lowering the cost of OLEDs.

[0004] Therefore, developing more types of organic narrow-spectrum luminescent materials with better electroluminescence properties is one of the key issues in achieving the above-mentioned expectations. Summary of the Invention

[0005] To achieve this objective, the present invention adopts the following technical solution:

[0006] This invention provides an organic compound having the structure shown in formula (1).

[0007]

[0008] In equation (1), Z1, Z2, and Z3 are each independently selected from CR1 or N; and at least one of Z1, Z2, and Z3 is CR1, which is the structure shown in equation a;

[0009] R1 is the structure shown in formula a, or R1 is independently selected from one of the following groups: hydrogen, halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted: C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl;

[0010] R1 is not connected to adjacent groups or is connected to them by chemical bonds to form a ring;

[0011] In formula a, X 11 X 12 X 13 X 14 X 15 Each is independently selected from CR2 or N; and X 11 X 12 X 13 X 14 X 15 At least two of them are N;

[0012] R2 is independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, and any one of the following groups, either unsubstituted or R'-substituted: C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; when R2 is selected from aryl or heteroaryl structures, R2 is connected to the structure of formula a by a single bond or by fusion.

[0013] The R2 group is not connected to adjacent groups or is connected to them by chemical bonds to form a ring;

[0014] In equation (1), Ar1 has the structure shown in equation b:

[0015] In formula b, ring A is selected from one of unsubstituted or R'-substituted C6 to C60 aromatic rings, or unsubstituted or R'-substituted C3 to C60 heteroaromatic rings;

[0016] In formula b, R is one of the following: unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl.

[0017] The R group is not connected to adjacent groups or is connected to them by chemical bonds to form a ring;

[0018] In equation (1), X is selected from CR 11 R 12 SiR 13 R 14 N-Ar2, O or S;

[0019] R 11 R 12 R 13 R 14 Each of the following is independently one of unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C6-C60 aryl, or unsubstituted or R'-substituted C3-C60 heteroaryl;

[0020] The R 11 With R 12 The R are either not connected or linked by chemical bonds to form a ring. 13 With R 14 They are either not connected to each other or linked together by chemical bonds to form a ring;

[0021] Ar2 is independently selected from one of unsubstituted or R'-substituted C6-C60 aromatic rings or unsubstituted or R'-substituted C3-C60 heteroaromatic rings;

[0022] In equation (1), X1, X2, X3, X4, Y1, Y2, Y3, and Y4 are each independently selected from CR3 or N;

[0023] R3 is independently selected from one of the following groups: hydrogen, halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted: C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl; R3 is connected to the parent structure of formula (1) by a single bond or by fused bonding;

[0024] The R3 group is not connected to adjacent groups or is connected to them by chemical bonds to form a ring;

[0025] Each of the above R' is independently selected from one or a combination of two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0026] Furthermore, in equation (1), it is preferable that X4 and Ar1 are not connected.

[0027] Furthermore, in equation (1), X is selected from CR 11 R 12 SiR 13 R 14 Or N-Ar2; R 11 R 12 R 13 R 14 Each of the following is independently one of an unsubstituted or R'-substituted C1-C10 straight-chain or branched alkyl group, an unsubstituted or R'-substituted C3-C10 cycloalkyl group, an unsubstituted or R'-substituted C6-C30 aryl group, or an unsubstituted or R'-substituted C3-C30 heteroaryl group.

[0028] Furthermore, the compound of the present invention has the structure shown in formula (2):

[0029]

[0030] In formula (2), the definitions of Z1, Z2, Z3, X1, X2, X3, X4, Y1, Y2, Y3, and Y4 are the same as those in formula (1); the definition of R is the same as that in formula b; R is not connected to adjacent groups or is connected to form a ring through chemical bonds;

[0031] In equation (2), Y4 and Y5 are either not connected or connected by a single bond;

[0032] In equation (2), X5, X6, X7, and X8 are each independently selected from CR4 or N; Y5, Y6, Y7, and Y8 are each independently selected from CR5 or N.

[0033] In X5, X6, X7, and X8, two adjacent pairs may be connected or not; in Y5, Y6, Y7, and Y8, two adjacent pairs may be connected or not.

[0034] R4 and R5 are each independently selected from one or a combination of two of the following: hydrogen, halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylthio, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylether, C3-C60 heteroarylether, C6-C60 arylthioether, C3-C60 heteroarylthioether, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0035] The R4 group is not connected to adjacent groups or is connected to them by chemical bonds to form a ring;

[0036] The R5 group is not connected to adjacent groups or is linked to them by chemical bonds to form a ring.

[0037] Furthermore, in formula (1), X5, X6, X7, and X8 are each independently selected from CR4, and Y5, Y6, Y7, and Y8 are each independently selected from CR5; R4 and R5 are each independently selected from one or a combination of two of the following: hydrogen, halogen, cyano, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0038] Furthermore, in formula (1), one of Z1, Z2, and Z3 is CR1, and R1 is the structure shown in formula a; preferably, one of Z1, Z2, and Z3 is CR1, and R1 is the structure shown in formula a, and the other two of Z1, Z2, and Z3 are CR1, and R1 is hydrogen;

[0039] In formula a, X 11 X 12 X 13 X 14 X 15 Two or three of them are N, X 11 X 12 X 13 X 14 X 15 The other three or two are each independently selected from CR2;

[0040] R2 is independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, and any one of the following groups, either unsubstituted or R'-substituted: C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; when R2 is selected from aryl or heteroaryl structures, R2 is connected to the structure of formula a by a single bond or by fusion.

[0041] R' is independently selected from one or a combination of two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0042] Furthermore, the compounds of the present invention have the structure shown in formula (3-1) or (3-2):

[0043]

[0044] Among them, the definitions of Z1, Z2, Z3, X1, X2, X3, X4, Y1, Y2, Y3, and Y4 are the same as those in formula (1); the definition of R is the same as that in formula b; R is not connected to adjacent groups or is connected to form a ring by chemical bonds;

[0045] The definitions of X5, X6, X7, X8, Y5, Y6, Y7, and Y8 are the same as those in equation (2);

[0046] M1 and M2 are each independently selected from single bonds and NR. 15 O, S, CR 16 R 17 or SiR 18 R 19 Any one of them, and M1 and M2 are not both single bonds;

[0047] Preferably, M1 and M2 are each independently selected from single bonds or NR bonds. 15 Furthermore, M1 and M2 are not both single bonds;

[0048] R 15 R 16 R 17 R 18 R 19 Each is independently selected from one or a combination of two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0049] Y 10 Y 11 Y 12 Y 13 Each is independently selected from CR6 or N; R6 is selected from one or a combination of two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0050] Furthermore, in equation (2), Z2 is CR1, and R1 is the structure shown in equation a; in equation a, X 11 X 12 X 13 X 14 X 15 Two or three of them are N, X11 X 12 X 13 X 14 X 15 The other three or two are each independently selected from CR2;

[0051] Each R2 is independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted groups of any one of the following: C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl; when R2 is selected from aryl or heteroaryl structures, R2 is connected to the structure of formula a by a single bond or by fusion;

[0052] Preferably, R2 is independently selected from one or a combination of two of the following: hydrogen, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl; when R2 is selected from aryl or heteroaryl structures, R2 is connected to the structure of formula a by a single bond or by fusion.

[0053] Furthermore, it is preferred that formula a is one of the following groups, either unsubstituted or R'-substituted: pyrimidine, triazine, quinazoline, or quinoline;

[0054] Preferably, formula a is an unsubstituted or R'-substituted pyrimidine or triazine;

[0055] R' is independently selected from one of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

[0056] Furthermore, Y4 and Y5 are connected by a single bond; R and X5 are not connected; more preferably, R is selected from one of the following groups that are unsubstituted or R' substituted: phenyl, biphenyl; each of R' is independently selected from one of halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl.

[0057] Further, in formula b, R is one of unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl; R' is independently selected from one or a combination of two of C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

[0058] Preferably, R is an unsubstituted or R'-substituted C6-C60 aryl group;

[0059] More preferably, formula b is selected from one of the following groups:

[0060]

[0061] Furthermore, in formulas (1) and (2), X1, X2, X3, X4, Y1, Y2, Y3, and Y4 are each independently selected from CR3, and R3 is each independently selected from one or a combination of two of the following: C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl. R3 is not connected to adjacent groups or is linked to form a ring through chemical bonds.

[0062] In this invention, the "substituted or unsubstituted" group can replace one substituent or multiple substituents. When there are multiple substituents, they can be selected from different substituents. In this invention, when the same expression is used, they all have the same meaning, and the selection range of substituents is as shown above and will not be repeated one by one.

[0063] In this specification, the expression Ca to Cb represents that the group has a to b carbon atoms. Unless otherwise specified, the number of carbon atoms generally does not include the number of carbon atoms of the substituents.

[0064] In this specification, the way a ring structure is represented by "—" indicates that the connection point is located at any position on the ring structure where bonding can occur.

[0065] In this specification, "each independently" means that when there are multiple subjects, they may be the same or different from each other.

[0066] In this invention, unless otherwise specified, the description of chemical elements generally includes the concept of their isotopes. For example, the description of "hydrogen (H)" includes its isotopes. 1 H (protium or H), 2 The concept of H (deuterium or D); carbon (C) includes... 12 C 13 C, etc., will not be elaborated further.

[0067] In this invention, heteroatoms generally refer to atoms or groups of atoms selected from N, O, S, P, Si and Se, preferably selected from N, O and S.

[0068] Examples of halogens in this specification include fluorine, chlorine, bromine, and iodine.

[0069] In this invention, unless otherwise specified, aryl and heteroaryl groups include both monocyclic and fused-ring types.

[0070] In this invention, C6-C60 can be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, or C58, etc.

[0071] C3-C60 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, or C58, etc.

[0072] C1-C20 can all be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0073] C3-C20 can all be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18 or C19, etc.

[0074] C6-C30 can all be C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0075] C3-C30 can all be C3, C4, C5, C6, C9, C10, C12, C14, C16, C18, C20, C22, C24, C26 or C28, etc.

[0076] C2-C10 can all be C2, C3, C4, C5, C6, C7, C8, C9 or C10.

[0077] In this invention, the substituted or unsubstituted C6-C60 aryl groups include monocyclic aryl groups and fused-ring aryl groups, preferably C6-C30 aryl groups, and more preferably C6-C20 aryl groups. A monocyclic aryl group refers to a molecule containing at least one phenyl group. When a molecule contains at least two phenyl groups, the phenyl groups are independent of each other and connected by a single bond, exemplarily including phenyl, biphenyl, and terphenyl. Specifically, the biphenyl group includes 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, meta-terphenyl-4-yl, meta-terphenyl-3-yl, and meta-terphenyl-2-yl. A fused-ring aryl group refers to a molecule containing at least two aromatic rings, where the aromatic rings are not independent of each other but share two adjacent carbon atoms fused together. Examples include: naphthyl, anthracene, phenanthrene, indene, fluorenyl, fluoranthyl, triphenylene, pyrene, perylene, etc. Naphthyl, 2-naphthyl, and their derivative groups, etc. The naphthyl includes 1-naphthyl or 2-naphthyl; the anthraceneyl is selected from 1-anthrayl, 2-anthrayl, and 9-anthrayl; the fluorenyl is selected from 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrene is selected from 1-pyrene, 2-pyrene, and 4-pyrene; the 2-tetraphenyl is selected from 1-2 ... The fluorene derivative group is selected from 9,9-dimethylfluorenyl, 9,9-diethylfluorenyl, 9,9-dipropylfluorenyl, 9,9-dibutylfluorenyl, 9,9-dipentylfluorenyl, 9,9-dihexylfluorenyl, 9,9-diphenylfluorenyl, 9,9-dinaphthylfluorenyl, 9,9'-spirodifluorenyl, and benzo[a]fluorenyl.

[0078] The C3-C60 heteroaryl groups mentioned in this invention include monocyclic heteroaryl groups and fused-ring heteroaryl groups, preferably C3-C30 heteroaryl groups, more preferably C4-C20 heteroaryl groups, and even more preferably C5-C12 heteroaryl groups. A monocyclic heteroaryl group refers to a molecule containing at least one heteroaryl group. When a molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and connected by a single bond. Examples of monocyclic heteroaryl groups include furanyl, thiophene, pyrrole, and pyridinyl. A fused-ring heteroaryl group refers to a molecule containing at least one aromatic heterocycle and an aromatic ring (aromatic heterocycle or aromatic ring), and the two are not independent of each other but share a group consisting of two adjacent atoms fused together. Examples of fused-ring heteroaryl groups include: benzofuranyl, benzothiophenyl, isobenzofuranyl, indolyl, dibenzofuranyl, dibenzothiophenyl, carbazoyl, acridineyl, isobenzofuranyl, isobenzothiophenyl, benzocarbazoyl, azircarbazoyl, phenothiazinyl, phenothiazinyl, 9-phenylcarbazoyl, 9-naphthylcarbazoyl, dibenzocarbazoyl, indolocarbazoyl, etc.

[0079] The aryl group in this invention can be exemplified by the monovalent group composed of the above-mentioned aryl and heteroaryl groups and oxygen.

[0080] In this invention, arylamino represents a group formed by replacing the hydrogen on an amino group with one or two aryl groups, wherein the linking site of the arylamino can be linked to the aryl group in the arylamino or to the N group in the arylamino, and the exemplary number of carbons and specific groups of the aryl group in the arylamino are the same as described above.

[0081] Examples of C6-C30 arylamino groups mentioned in this invention include phenylamino, methylphenylamino, naphthylamino, anthraceneylamino, phenanthreneamino, and biphenylamino.

[0082] Examples of C3-C30 heteroaryl amino groups mentioned in this invention include pyridinyl amino, pyrimidinyl amino, and dibenzofuranyl amino.

[0083] Unless otherwise specified, the chain alkyl groups mentioned in this invention include straight-chain alkyl groups and branched-chain alkyl groups. Specifically, substituted or unsubstituted C1-C30 chain alkyl groups are preferably substituted or unsubstituted C1-C16 chain alkyl groups, and more preferably substituted or unsubstituted C1-C10 chain alkyl groups. Examples of substituted or unsubstituted C1-C10 chain alkyl groups include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexyl, neohexyl, n-heptyl, n-octyl, 2-ethylhexyl, etc.

[0084] In this invention, the cycloalkyl group includes monocycloalkyl and polycycloalkyl; wherein, monocycloalkyl refers to an alkyl group containing a single ring structure; polycycloalkyl refers to a structure composed of two or more cycloalkyl groups sharing one or more carbon atoms on a ring; examples of C3-C20 cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, etc.

[0085] In this specification, the substituted or unsubstituted C1-C20 alkoxy group is preferably a substituted or unsubstituted C1-C10 alkoxy group. Examples of C1-C10 alkoxy groups include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentooxy, isopentoxy, hexoxy, heptoxy, octoxy, nonoxy, decoxy, undecoxy, dodecoxy, etc., among which methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentoxy, and isopentoxy are preferred, and methoxy is more preferred.

[0086] In this specification, the substituted or unsubstituted C1-C20 silanes and the substituted or unsubstituted C1-C10 silanes are examples of silanes substituted with groups listed in the above C1-C10 silanes, specifically including: methylsilane, dimethylsilane, trimethylsilane, ethylsilane, diethylsilane, triethylsilane, tert-butyldimethylsilane, tert-butyldiphenylsilane, etc.

[0087] In this specification, the C2-C10 alkenyl group is a hydrocarbon group containing at least one C=C double bond, and exemplary includes, but is not limited to: vinyl, propenyl, allyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, butadienyl, pentadienyl, etc.

[0088] It should be noted that while the possible effects of each group / feature have been described separately for ease of explanation in this application, this does not mean that these groups / features act in isolation. In fact, the reason for achieving good performance is essentially the optimized combination of the entire molecule, the result of the synergistic effect between various groups, rather than the effect of a single group.

[0089] More preferably, the organic compounds of the present invention have the structures shown in the following chemical formulas, but are not limited to the specific structural formulas described below:

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101] In a second aspect, the present invention provides an application of the organic compound as described in the first aspect, wherein the organic compound is applied to an organic electronic device.

[0102] Preferably, the organic electronic device includes an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin-film transistor, an organic field-effect transistor, an organic thin-film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner, or electronic paper; more preferably, it is an organic electroluminescent device. Preferably, the organic compound is used in the organic electroluminescent device. Preferably, the organic compound serves as a light-emitting layer material in the organic electroluminescent device.

[0103] Thirdly, the present invention provides an organic electroluminescent device, the organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode; the organic layer comprising at least one organic compound as described in the first aspect.

[0104] Preferably, the organic layer comprises at least one organic compound with the structure shown in M1-M2O4. Preferably, the organic layer comprises a light-emitting layer, which comprises at least one organic compound as described in the first aspect, and more preferably at least one organic compound with the structure shown in M1-M2O4. Preferably, the light-emitting layer comprises a host material and a dopant material, the dopant material comprising at least one organic compound as described in the first aspect.

[0105] More preferably, the organic compound provided by the present invention is used as a fluorescent dopant material for the light-emitting layer.

[0106] Preferably, the mass percentage of the doped material in the light-emitting layer is 0.1-10%, for example, it can be 0.2%, 0.5%, 0.8%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 8% or 9%, and more preferably 0.3-3%.

[0107] Preferably, the host material includes any one or a combination of at least two of the following: P-type host material, N-type host material, and monomolecular excitosome host material.

[0108] More preferably, the luminescent layer further includes a sensitizer. Preferably, the sensitizer includes any one or a combination of at least two of thermally activated delayed fluorescence materials and phosphorescent materials. Preferably, the energy of the lowest triplet state (T1) of the sensitizer is greater than or equal to the energy of the lowest singlet state (S1) of the organic compound of the present invention.

[0109] Preferably, the mass percentage of the sensitizer in the luminescent layer is 0.1-40%, for example, it can be 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 4%, 5%, 6%, 7%, 8%, 9%, 10%, 15%, 20%, 25%, 30% or 35%, etc.

[0110] Preferably, the sensitizer comprises a phosphorescent material, and the phosphorescent material in the luminescent layer has a mass percentage content of 0.1%-10%.

[0111] More preferably, the phosphorescent material in the light-emitting layer has a mass percentage content of 1%-8%.

[0112] Preferably, the sensitizer is a thermally activated delayed fluorescence material, and the mass percentage of the thermally activated delayed fluorescence material in the luminescent layer is 1-40%.

[0113] Preferably, the organic layer further includes a hole transport region and an electron transport region. Preferably, the hole transport region includes any one or a combination of at least two of a hole injection layer, a hole transport layer, and an electron blocking layer. Preferably, the electron transport region includes any one or a combination of at least two of an electron injection layer, an electron transport layer, and a hole blocking layer.

[0114] Fourthly, the present invention provides a display device comprising the organic electroluminescent device as described in the third aspect.

[0115] Compared with the prior art, the present invention has the following beneficial effects:

[0116] The organic compounds provided by this invention involve the design and mutual compounding of ortho-position sterically hindered groups and electron-withdrawing groups (triazine / pyrimidine) on a boron-nitrogen multi-resonance core structure. This allows for the adjustment of light color while maintaining the narrow emission spectrum and high luminous efficiency of the multi-resonance material. These organic compounds possess excellent electroluminescence properties, narrow spectral characteristics, and thermal stability. When used in organic electroluminescent devices, they can serve as fluorescent dopant materials in the emitting layer, effectively improving device lifetime decay and efficiency roll-off, enhancing luminous efficiency, extending device lifetime, and providing higher color purity. Detailed Implementation

[0117] The organic compounds represented by Formula I of this invention can be synthesized using organic synthesis methods known in the art. Exemplary synthetic routes are given below, but those skilled in the art can also obtain them using other known methods.

[0118] In one specific embodiment, the organic compound can be prepared via the following synthetic route:

[0119]

[0120] The specific preparation methods of the boron-containing organic compounds of the present invention will be described in detail below using several synthetic examples, but the preparation methods of the present invention are not limited to these synthetic examples.

[0121] It should be noted that obtaining the boron-containing organic compounds is not limited to the synthetic methods and raw materials used in this invention. Those skilled in the art can also select other methods or routes to obtain the boron-containing organic compounds proposed in this invention. The compounds, solvents, and reagents used in the synthetic methods not mentioned in this invention are all commercially available raw material products, which can be purchased from the domestic chemical product market or prepared in-house using these raw material products according to known methods.

[0122] The intermediates and target products in the following synthesis examples of the present invention were analyzed and detected using a high-resolution mass spectrometer and matrix-assisted laser desorption / ionization (MALDI) technology.

[0123] Synthesis Example 1: Synthesis of Boron-Containing Organic Compound M4

[0124]

[0125] (1) Synthesis of intermediate M4-1:

[0126] SM1 (25g), SM2 (29g), dba palladium (7.5g), tri-tert-butylphosphine tetrafluoroborate (4.76g), sodium tert-butoxide (11.8g), and toluene (500mL) were added to a 1000mL three-necked flask, purged with nitrogen three times, and reacted at 50℃ for 12 hours.

[0127] The reaction solution was cooled to room temperature, mixed with silica gel, and purified by column chromatography to obtain intermediate M4-132 g of white solid.

[0128] (2) Synthesis of intermediate M4-2:

[0129] M4-1 (30g), SM3 (33.6g), dba palladium (0.5g), S-phos (0.45g), sodium tert-butoxide (7.9g), and toluene (600mL) were added to a 1000mL single-necked flask, purged with nitrogen three times, and heated to reflux for 12 hours.

[0130] The reaction solution was cooled to room temperature, mixed with silica gel, and purified by column chromatography to obtain intermediate M4-247 g of white solid.

[0131] (3) Synthesis of intermediate M4-3:

[0132] Intermediate M4-2 (45 g) was added to a 1000 mL three-necked flask, followed by xylene (450 mL). The mixture was purged with nitrogen three times, and the reaction system was cooled to -40 °C. 72 mL of 1.6 M tert-butyllithium was added dropwise, and the mixture was then heated to 60 °C and reacted for 2.5 h. The reaction system was then cooled to -40 °C, and 13.3 mL of boron tribromide was added. The mixture was then heated to 60 °C and reacted for 1.5 h. The reaction system was then cooled to -40 °C again, and 38 mL of N,N-diisopropylethylamine was added. Finally, the reaction system was heated to 120 °C and reacted for 5 h. After the reaction was cooled to room temperature, methanol was added dropwise and stirred for 30 minutes. The mixture was filtered, dried, and recrystallized from dichloromethane / ethanol to obtain intermediate M4-315 g.

[0133] (4) Synthesis of intermediate M4-4:

[0134] Intermediate M4-3 (14g), pinacol diboronate (18.8g), potassium acetate (4.3g), palladium 132, and toluene (280mL) were added to a 500mL three-necked flask, purged with nitrogen three times, and heated to 100℃ for 5 hours.

[0135] The reaction solution was cooled to room temperature and filtered. The filtrate was concentrated to dryness and purified by column chromatography to obtain intermediate M4-47 g.

[0136] (5) Synthesis of target product M4:

[0137] Intermediate M4-3 (5g), 2-chloro-4,6-diphenyl-1,3,5-triazine (1.29g), tetra-triphenylphosphine palladium (0.28g), potassium carbonate (1.3g), dioxane (200mL), and water (20mL) were added to a 500mL single-necked flask, purged with nitrogen three times, and heated to 100℃ for 12 hours.

[0138] The reaction solution was cooled to room temperature, concentrated to dryness, purified by column chromatography, and the product spot was collected and concentrated to dryness. The 1.5 g solid obtained by recrystallization from dichloromethane was the target product. The molecular ion mass determined by mass spectrometry analysis was 1143.32 (theoretical value: 1143.54).

[0139] Synthesis Example 2: Synthesis of Boron-Containing Organic Compound M60

[0140]

[0141] (1) Synthesis of intermediate M60-1:

[0142] The synthesis scheme was the same as that for M4-1, and the intermediate M60-1 was purified by column chromatography to obtain 30.6 g of white solid.

[0143] (2) Synthesis of intermediate M60-2:

[0144] Add M60-1 (26.0g), SM3 (13.66g), cesium carbonate (20g), and DMF (260mL) to a 500mL single-necked flask, purge with nitrogen three times, and heat to 100℃ to react overnight.

[0145] The reaction solution was quenched in water, filtered, the solid was collected and dried, and recrystallized from toluene / ethanol to give intermediate M60-235 g of white solid.

[0146] (3) Synthesis of intermediate M60-3:

[0147] The synthesis scheme is the same as that for M4-3, and the intermediate M60-312 g was purified by column chromatography.

[0148] (4) Synthesis of intermediate M60-4:

[0149] The synthesis scheme is the same as that for M4-4, and the intermediate M60-46 g was purified by column chromatography.

[0150] (5) Synthesis of the target product M60:

[0151] The synthesis scheme is the same as that for M4. The 1.2g solid obtained by recrystallization of dichloromethane is the molecular ion mass of the target product M60, determined by mass spectrometry analysis: 1113.25 (theoretical value: 1113.59).

[0152] Synthesis Example 3: Synthesis of Boron-Containing Organic Compound M15

[0153]

[0154] (1) Synthesis of intermediate M15-1:

[0155] The synthesis scheme was the same as that for M4-1, and the intermediate M15-1 was purified by column chromatography to give 32.1 g of white solid.

[0156] (2) Synthesis of intermediate M15-2:

[0157] The synthesis scheme was the same as that for M60-2. After recrystallization and purification, intermediate M15-2 34.2 g of white solid was obtained.

[0158] (3) Synthesis of intermediate M15-3:

[0159] The synthesis scheme is the same as that for M4-3, and the intermediate M15-3 was purified by column chromatography (13.4 g).

[0160] (4) Synthesis of intermediate M15-4:

[0161] The synthesis scheme is the same as that for M4-4, and the intermediate M15-4 7.5g was purified by column chromatography.

[0162] (5) Synthesis of the target product M15:

[0163] The synthesis scheme is the same as that for M4. The 1.3g solid obtained by recrystallization of dichloromethane is the target product M15. The molecular ion mass determined by mass spectrometry analysis is 1049.78 (theoretical value: 1049.56).

[0164] Synthesis Example 4: Synthesis of Boron-Containing Organic Compound M107

[0165]

[0166] (1) Synthesis of intermediate M107-1:

[0167] The synthesis scheme was the same as that for M4-1. After purification by column chromatography, 30.8 g of intermediate M107-1 was obtained as a white solid.

[0168] (2) Synthesis of intermediate M107-2:

[0169] The synthesis scheme was the same as that for M60-2. After recrystallization and purification, intermediate M107-2 32.6 g of white solid was obtained.

[0170] (3) Synthesis of intermediate M107-3:

[0171] The synthesis scheme is the same as that for M4-3, and the intermediate M107-3 was purified by column chromatography (14.2 g).

[0172] (4) Synthesis of intermediate M107-4:

[0173] The synthesis scheme is the same as that for M4-4, and the intermediate M107-47.8g was purified by column chromatography.

[0174] (5) Synthesis of the target product M107:

[0175] The synthesis scheme is the same as that for M4. The 1.6g solid obtained by recrystallization of dichloromethane is the target product M107. The molecular ion mass determined by mass spectrometry analysis is 937.62 (theoretical value: 937.53).

[0176] Synthesis Example 5: Synthesis of Boron-Containing Organic Compound M146

[0177]

[0178] (1) Synthesis of intermediate M146-1:

[0179] The synthesis scheme was the same as that for M4-1, and the intermediate M146-1 was purified by column chromatography to give 31.3 g of white solid.

[0180] (2) Synthesis of intermediate M146-2:

[0181] The synthesis scheme was the same as that for M4-2. After recrystallization and purification, intermediate M146-2 39.2 g of white solid was obtained.

[0182] (3) Synthesis of intermediate M146-3:

[0183] The synthesis scheme was the same as that for M4-3, and the intermediate M146-3 was purified by column chromatography (15.4 g).

[0184] (4) Synthesis of intermediate M146-4:

[0185] The synthesis scheme is the same as that for M4-4, and the intermediate M146-46.8g was purified by column chromatography.

[0186] (5) Synthesis of the target product M146:

[0187] The synthesis scheme is the same as that for M4. The 1.4g solid obtained by recrystallization of dichloromethane is the molecular ion mass of the target product M146, determined by mass spectrometry analysis: 1194.82 (theoretical value: 1194.76).

[0189] In a preferred embodiment, the organic electroluminescent device (OLED device) includes a first electrode and a second electrode, and an organic layer located between the electrodes. The organic layer can be further divided into multiple regions, such as a hole transport region, a light-emitting layer, and an electron transport region; the light-emitting layer contains at least one organic compound as described in the first aspect, and more preferably contains at least one organic compound with the structure shown in M1-M178.

[0190] In a preferred embodiment, the organic electroluminescent device includes a first electrode, a plurality of light-emitting functional layers (organic layers), and a second electrode arranged sequentially. The organic layers include a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer arranged sequentially, with the hole injection layer in contact with the first electrode (anode). The organic layer (preferably the light-emitting layer) contains at least one organic compound as described in the first aspect, and more preferably contains at least one organic compound with the structure shown in M1-M178.

[0191] In a preferred embodiment, a substrate can be used below the first electrode or above the second electrode. The substrate is typically made of glass or polymer material possessing excellent mechanical strength, thermal stability, water resistance, and transparency. Furthermore, the substrate used for a display may also incorporate thin-film transistors (TFTs).

[0192] The first electrode can be formed by sputtering or depositing the material to be used as the first electrode on a substrate. When the first electrode is used as the anode, it can be a transparent conductive oxide material such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof. When the first electrode is used as the cathode, it can be a metal or alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.

[0193] Organic layers can be formed on electrodes using methods such as vacuum thermal evaporation, spin coating, and printing. The compounds used as organic layers can be small organic molecules, large organic molecules, or polymers, as well as combinations thereof.

[0194] The hole transport region is located between the anode and the emissive layer. The hole transport region can be a single-layer hole transport layer (HTL), including single-layer hole transport layers containing only one compound and single-layer hole transport layers containing multiple compounds. Alternatively, the hole transport region can be a multilayer structure including at least one of a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL); wherein the HIL is located between the anode and the HTL, and the EBL is located between the HTL and the emissive layer.

[0195] The material for the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylene ethylene, polyaniline / dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (Pani / PSS), aromatic amine derivatives, wherein the aromatic amine derivatives include compounds shown in HT-1 to HT-51 below; or any combination thereof.

[0196]

[0197]

[0198]

[0199]

[0200] The hole injection layer is located between the anode and the hole transport layer. The hole injection layer can be a single compound material or a combination of multiple compounds. For example, the hole injection layer can be one or more compounds of HT-1 to HT-51 described above, or one or more compounds of HI-1 to HI-3 described below; it can also be one or more compounds of HT-1 to HT-51 doped with one or more compounds of HI-1 to HI-3 described below.

[0201]

[0202] The emissive layer consists of a luminescent dye (i.e., a dopant) that emits different wavelengths of light and a host material. The emissive layer can be a monochromatic layer emitting a single color such as red, green, or blue. Multiple monochromatic emissive layers of different colors can be arranged in a planar pattern according to pixel design, or they can be stacked together to form a colored emissive layer. When different colored emissive layers are stacked together, they can be separated from each other or connected to each other. The emissive layer can also be a single colored emissive layer that simultaneously emits different colors such as red, green, and blue.

[0203] In one aspect of the invention, the light-emitting layer employs a combination of phosphorescence-sensitized luminescence and thermally activated sensitized fluorescence luminescence. The main material of the light-emitting layer is selected from, but not limited to, one or more combinations of PH-1 to PH-85 mentioned above.

[0204]

[0205]

[0206]

[0207]

[0208]

[0209] In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. Its sensitizer, the phosphorescent material, may be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-60 listed below.

[0210]

[0211]

[0212]

[0213] ; where D represents deuterium.

[0214] In one aspect of the invention, the luminescent layer employs thermally activated sensitized fluorescence luminescence technology. The sensitizer of the luminescent layer, i.e., the thermally activated delayed fluorescence material, can be selected from, but is not limited to, one or more combinations of TDE1-TDE37 listed below.

[0215]

[0216]

[0217]

[0218] In one aspect of the present invention, an electron blocking layer (EBL) is located between the hole transport layer and the light-emitting layer. The electron blocking layer may employ, but is not limited to, one or more compounds of HT-1 to HT-51 described above, or one or more compounds of PH-47 to PH-77 described above; or a mixture of one or more compounds of HT-1 to HT-51 and one or more compounds of PH-47 to PH-77 may be employed.

[0219] The organic layer of an OLED may also include an electron transport region between the light-emitting layer and the cathode. The electron transport region can be a single-layer electron transport layer (ETL), including single-layer electron transport layers containing only one compound and single-layer electron transport layers containing multiple compounds. Alternatively, the electron transport region can be a multilayer structure including at least one of an electron injection layer (EIL), an electron transport layer (ETL), and a hole blocking layer (HBL).

[0220] In one aspect of the present invention, the electron transport layer material may be selected from, but not limited to, one or more combinations of ET-1 to ET-73 listed below.

[0221]

[0222]

[0223]

[0224]

[0225] In one aspect of the present invention, a hole blocking layer (HBL) is located between the electron transport layer and the light-emitting layer. The hole blocking layer may employ, but is not limited to, one or more compounds of ET-1 to ET-73, or one or more compounds of PH-1 to PH-46; or a mixture of one or more compounds of ET-1 to ET-73 and one or more compounds of PH-1 to PH-46 may be employed.

[0226] The device may also include an electron injection layer located between the electron transport layer and the cathode. The electron injection layer material includes, but is not limited to, one or more combinations of the following: LiQ, LiF, NaCl, CsF, Li2O, Cs2CO3, BaO, Na, Li, Ca, Mg, Yb.

[0227] Device Example 1

[0228] An organic electroluminescent device includes an anode (ITO), a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode (Al) stacked sequentially.

[0229] The fabrication method of this organic electroluminescent device is as follows:

[0230] (1) The glass substrate coated with ITO transparent conductive layer was ultrasonically treated in commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in acetone / ethanol mixed solvent, baked in a clean environment until the moisture was completely removed, cleaned with ultraviolet light and ozone, and bombarded with low-energy cation beam.

[0231] (2) Place the glass substrate with the anode inside the vacuum chamber and evacuate it to a vacuum level less than 1 × 10⁻⁶. -5 Pa, a mixture of HT-4:HI-3 (97 / 3, w / w) was vacuum-deposited on the above-mentioned anodic layer as a hole injection layer, and the thickness of the deposited film was 10 nm.

[0232] (3) The compound HT-4 was vacuum-deposited on the hole injection layer as a hole transport layer, and the total film thickness was 60 nm.

[0233] (4) The compound HT-36 was vacuum-deposited on the hole transport layer as an electron blocking layer, and the total film thickness was 5 nm.

[0234] (5) A light-emitting layer is vacuum-deposited on the electron blocking layer. The light-emitting layer includes a host material, a sensitizer, and a dopant material (fluorescent dye). The doping ratio is adjusted by adjusting the evaporation rate of each material using a multi-source co-evaporation method. The total film thickness is 40 nm.

[0235] When using phosphorus-sensitized luminescence technology, the ratio of the host material, phosphorus sensitizer, and dopant is 94.2:5:0.8 (w / w / w). The host material is a PH-61:PH-3 (50 / 50, w / w) mixed host, the phosphorus sensitizer is GPD-29, and the dopant is the organic compound provided by this invention.

[0236] (6) The compound ET-23 was vacuum-deposited on the light-emitting layer as a hole blocking layer, and the total film thickness was 5 nm.

[0237] (7) A mixture of compound ET-69:ET-57 (50 / 50, w / w) was vacuum-deposited on the hole blocking layer as an electron transport layer, with a total film thickness of 25 nm.

[0238] (8) Vacuum evaporation of LiF as an electron injection layer on the electron transport layer with a thickness of 1 nm;

[0239] (9) An Al layer with a thickness of 150 nm is vacuum-deposited on the electron injection layer as the cathode of the device to obtain the organic electroluminescent device; the total deposition rate of all organic layers and LiF is controlled at 0.1 nm / s, and the deposition rate of the metal electrode is controlled at 1 nm / s.

[0240] Device Examples 2-14, Device Comparative Examples 1-3

[0241] An organic electroluminescent device is disclosed, which differs from device example 1 only in that the fluorescent dyes of the light-emitting layer are the compounds shown in Table 1; the other layers, thicknesses, materials and preparation methods are the same as those in device example 1.

[0242] The structures of the fluorescent dyes in Comparative Examples 1-3 are as follows:

[0243]

[0244] Device performance testing:

[0245] Under the same brightness, the driving voltage, lifetime, and external quantum efficiency of each organic electroluminescent device were measured using a digital source meter and a luminance meter.

[0246] Specifically, the voltage was increased at a rate of 0.1V per second, and the current density of the organic electroluminescent device was measured when it reached 10mA / cm². 2The voltage at that time is the driving voltage, and the luminance and external quantum efficiency (EQE, %) at that time are measured simultaneously; the lifetime test of LT95 is as follows: using a luminance meter at 10000 cd / m² 2 At a constant current, the brightness of the organic electroluminescent device decreased to 9500 cd / m² under the specified brightness. 2 The time is in hours; the test value of LT95 lifetime for Comparative Example 1 in Table 1 is recorded as 1.00, and the LT95 lifetime of Device Examples 1-14 are all ratios of their respective test values ​​to the test value of Comparative Example 1 (relative lifetime).

[0247] The test results are shown in Table 1:

[0248] Table 1:

[0249]

[0250]

[0251] Based on the performance data in Table 1, and compared with Comparative Examples 1-3, the boron-containing organic compound provided by this invention, as a dye for organic electroluminescent devices, has excellent performance due to its specific molecular structure advantages. It can effectively reduce the operating voltage, improve the external quantum efficiency of the device, and extend the device lifespan, making it a high-performance green light-emitting material.

[0252] Compared to Comparative Example 1, the compounds of this invention introduce pyrimidine or triazine electron-withdrawing groups at the para-position of the boron atom. Compared to pyridine substituents, pyrimidine or triazine electron-withdrawing groups can disperse the negative electrons of the BN core, resulting in better material stability under electroluminescence and improving device lifetime.

[0253] Compared to Comparative Examples 2 and 3, the steric group of formula a is introduced at the ortho position of the nitrogen atom in the compound of the present invention, which helps to restrict the structural relaxation of the molecule in the excited state, further narrows the emission spectrum of the material, and is beneficial to improving the efficiency of the device.

[0254] The applicant declares that the above embodiments illustrate the boron-containing organic compounds and their applications, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound having the structure shown in formula (1), In equation (1), Z1, Z2, and Z3 are each independently selected from CR1 or N; and at least one of Z1, Z2, and Z3 is CR1, which is the structure shown in equation a; R1 is the structure shown in formula a, or R1 is independently selected from one of the following groups: hydrogen, halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted: C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl; R1 is not connected to adjacent groups or is connected to them by chemical bonds to form a ring; In formula a, X 11 X 12 X 13 X 14 X 15 Each is independently selected from CR2 or N; and X 11 X 12 X 13 X 14 X 15 At least two of them are N; R2 is independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, and any one of the following groups, either unsubstituted or R'-substituted: C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; when R2 is selected from aryl or heteroaryl structures, R2 is connected to the structure of formula a by a single bond or by fusion. The R2 group is not connected to adjacent groups or is connected to them by chemical bonds to form a ring; In equation (1), Ar1 has the structure shown in equation b: In formula b, ring A is selected from one of unsubstituted or R'-substituted C6 to C60 aromatic rings, or unsubstituted or R'-substituted C3 to C60 heteroaromatic rings; In formula b, R is one of the following: unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C6-C60 aryl, and unsubstituted or R'-substituted C3-C60 heteroaryl. The R group is not connected to adjacent groups or is connected to them by chemical bonds to form a ring; In equation (1), X is selected from CR 11 R 12 SiR 13 R 14 N-Ar2, O or S; R 11 R 12 R 13 R 14 Each of the following is independently one of unsubstituted or R'-substituted C1-C20 straight-chain or branched alkyl, unsubstituted or R'-substituted C3-C20 cycloalkyl, unsubstituted or R'-substituted C6-C60 aryl, or unsubstituted or R'-substituted C3-C60 heteroaryl; The R 11 With R 12 The R are either not connected or linked by chemical bonds to form a ring. 13 With R 14 They are either not connected to each other or linked together by chemical bonds to form a ring; Ar2 is independently selected from one of unsubstituted or R'-substituted C6-C60 aryl groups or unsubstituted or R'-substituted C3-C60 heteroaryl groups; In equation (1), X1, X2, X3, X4, Y1, Y2, Y3, and Y4 are each independently selected from CR3 or N; R3 is independently selected from one of the following groups: hydrogen, halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted: C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl; R3 is connected to the parent structure of formula (1) by a single bond or by fused bonding; The R3 group is not connected to adjacent groups or is connected to them by chemical bonds to form a ring; Each of the above R' is independently selected from one or a combination of two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

2. The organic compound according to claim 1, characterized in that, In formula b, R is one of unsubstituted or R'-substituted C6-C60 aryl or unsubstituted or R'-substituted C3-C60 heteroaryl; In equation (1), X4 and Ar1 are not connected.

3. The organic compound according to claim 1, characterized in that, In equation (1), X is selected from CR 11 R 12 SiR 13 R 14 Or N-Ar2; R 11 R 12 R 13 R 14 Each of the following is independently one of an unsubstituted or R'-substituted C1-C10 straight-chain or branched alkyl group, an unsubstituted or R'-substituted C3-C10 cycloalkyl group, an unsubstituted or R'-substituted C6-C30 aryl group, or an unsubstituted or R'-substituted C3-C30 heteroaryl group.

4. The organic compound according to claim 1, characterized in that, It has the structure shown in equation (2): In formula (2), the definitions of Z1, Z2, Z3, X1, X2, X3, X4, Y1, Y2, Y3, and Y4 are the same as those in formula (1); the definition of R is the same as that in formula b; R is not connected to adjacent groups or is connected to form a ring through chemical bonds; In equation (2), Y4 and Y5 are either not connected or connected by a single bond; In equation (2), X5, X6, X7, and X8 are each independently selected from CR4 or N; Y5, Y6, Y7, and Y8 are each independently selected from CR5 or N. In X5, X6, X7, and X8, two adjacent pairs may be connected or not; in Y5, Y6, Y7, and Y8, two adjacent pairs may be connected or not. R4 and R5 are each independently selected from one or a combination of two of the following: hydrogen, halogen, cyano, C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylthio, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylether, C3-C60 heteroarylether, C6-C60 arylthioether, C3-C60 heteroarylthioether, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. The R4 group is not connected to adjacent groups or is connected to them by chemical bonds to form a ring; The R5 group is not connected to adjacent groups or is linked to them by chemical bonds to form a ring.

5. The organic compound according to claim 4, characterized in that, X5, X6, X7, and X8 are each independently selected from CR4, and Y5, Y6, Y7, and Y8 are each independently selected from CR5. R4 and R5 are each independently selected from one or a combination of two of the following: hydrogen, halogen, cyano, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl.

6. The organic compound according to claim 1 or 4, characterized in that, One of Z1, Z2, and Z3 is CR1, and R1 is the structure shown in formula a; preferably, one of Z1, Z2, and Z3 is CR1, and R1 is the structure shown in formula a, and the other two of Z1, Z2, and Z3 are CR1, and R1 is hydrogen; In formula a, X 11 X 12 X 13 X 14 X 15 Two or three of them are N, X 11 X 12 X 13 X 14 X 15 The other three or two are each independently selected from CR2; R2 is independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, and any one of the following groups, either unsubstituted or R'-substituted: C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl; when R2 is selected from aryl or heteroaryl structures, R2 is connected to the structure of formula a by a single bond or by fusion. R' is independently selected from one or a combination of two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

7. The organic compound according to claim 4, characterized in that, It has the structure shown in equation (3-1) or (3-2): Among them, the definitions of Z1, Z2, Z3, X1, X2, X3, X4, Y1, Y2, Y3, and Y4 are the same as those in formula (1); the definition of R is the same as that in formula b; R is not connected to adjacent groups or is connected to form a ring by chemical bonds; The definitions of X5, X6, X7, X8, Y5, Y6, Y7, and Y8 are the same as those in equation (2); M1 and M2 are each independently selected from single bonds and NR. 15 O, S, CR 16 R 17 or SiR 18 R 19 Any one of them, and M1 and M2 are not both single bonds; R 15 R 16 R 17 R 18 R 19 Each is independently selected from one or a combination of two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. Y 10 Y 11 Y 12 Y 13 Each is independently selected from CR6 or N; R6 is selected from one or a combination of two of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. Preferably, M1 and M2 are each independently selected from single bonds or NR bonds. 15 Furthermore, M1 and M2 are not both single bonds.

8. The organic compound according to claim 4, characterized in that, Z2 is CR1, and R1 is the structure shown in formula a; in formula a, X 11 X 12 X 13 X 14 X 15 Two or three of them are N, X 11 X 12 X 13 X 14 X 15 The other three or two are each independently selected from CR2; Each R2 is independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, unsubstituted or R'-substituted groups of any one of the following: C1-C20 straight-chain or branched alkyl, C3-C20 cycloalkyl, C2-C20 alkenyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylsilyl, C6-C30 heteroarylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, C3-C60 heteroaryl; when R2 is selected from aryl or heteroaryl structures, R2 is connected to the structure of formula a by a single bond or by fusion; Preferably, R2 is independently selected from one or a combination of two of the following: hydrogen, C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C6-C30 aryl, and C3-C30 heteroaryl; when R2 is selected from aryl or heteroaryl structures, R2 is connected to the structure of formula a by a single bond or by fusion.

9. The organic compound according to claim 8, characterized in that, The formula a is one of the following groups, either unsubstituted or R'-substituted: pyrimidine, triazine, quinazoline, quinoline; R' is independently selected from one of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl. Preferably, formula a is an unsubstituted or R'-substituted pyrimidine or triazine.

10. The organic compound according to claim 4, characterized in that, Y4 and Y5 are connected by a single key; R and X5 are not connected. Preferably, R is selected from one of the following groups: phenyl or biphenyl, either unsubstituted or R'-substituted. R' is independently selected from one of the following: halogen, cyano, nitro, hydroxyl, amino, C1-C20 straight-chain or branched alkyl, C2-C20 alkenyl, C3-C20 cycloalkyl, C1-C20 alkoxy, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C60 arylsilyl, C3-C60 heteroarylsilyl, C6-C60 arylamino, C3-C60 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl, and C3-C60 heteroaryl.

11. The organic compound according to claim 1, characterized in that, In formula b, R is one of unsubstituted or R'-substituted C6-C60 aryl, unsubstituted or R'-substituted C3-C60 heteroaryl; R' is independently selected from one or a combination of two of C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl. Preferably, R is an unsubstituted or R'-substituted C6-C60 aryl group; More preferably, formula b is selected from one of the following groups:

12. The organic compound according to claim 1 or 4, characterized in that, X1, X2, X3, X4, Y1, Y2, Y3, and Y4 are each independently selected from CR3, and R3 is each independently selected from one or a combination of two of the following: C1-C10 straight-chain or branched alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C1-C10 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C30 aryl, and C3-C30 heteroaryl. R3 is not connected to adjacent groups or is linked to them by chemical bonds to form a ring.

13. The organic compound according to claim 1, characterized in that, It has the following structure:

14. The use of the organic compound according to any one of claims 1 to 13, wherein the use is as a functional material in an organic electronic device, said organic electronic device being selected from organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin-film transistors, organic field-effect transistors, information tags, electronic artificial skin sheets, sheet-type scanners, or electronic paper; Preferably, the organic compound is used as a light-emitting layer material in an organic electroluminescent device, and more preferably as a light-emitting dye in the light-emitting layer.

15. An organic electroluminescent device, comprising a first electrode, a second electrode, and one or more light-emitting functional layers inserted between the first electrode and the second electrode, wherein the light-emitting functional layer contains an organic compound as described in any one of claims 1 to 13; Preferably, the light-emitting functional layer includes a light-emitting layer and at least one of a hole injection layer, a hole transport layer, an electron blocking layer, and an electron transport layer, wherein the light-emitting layer contains an organic compound as described in any one of claims 1 to 13.

16. A display device, characterized in that, The display device includes the organic electroluminescent device as described in claim 10.

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