A boron-containing resonance-type organic compound and an organic electroluminescent device comprising the same

Abstract

The present application relates to a kind of boron-containing resonance type organic compounds and the organic electroluminescent device comprising it, belong to semiconductor technical field, the present application provides the structure of organic compound as shown in general formula (1): The organic compound of the present application is used as the doping material in the light-emitting layer material of organic electroluminescent device, can be used as the red light doping material of the light-emitting layer of organic electroluminescent device, so as to improve the luminous efficiency and life of device.

Description

Technical Field

[0001] This invention relates to the field of semiconductor technology, and more particularly to a boron-containing resonant organic compound and an organic electroluminescent device containing the same. Background Technology

[0002] Organic light-emitting diodes (OLEDs) offer significant advantages over liquid crystal displays (LCDs), including being lighter and thinner, having higher color contrast, lower power consumption, faster response times, higher resolution, and greater flexibility. They are considered poised to dominate future display terminal products. With the advent of the 5G era, the new information display industry urgently needs iterative development. Early color gamut standards (BT.709 and DCIP3) are no longer sufficient to meet the high-quality technological demands of display products. To achieve ultra-high definition and higher image quality performance requirements, the new generation display standard (BT.2020) is driving the development of organic electroluminescent materials towards higher color purity, which necessitates that the core light-emitting material have a narrower emission spectrum. Currently, among the three commercially available OLED color display technologies (red, green, and blue), blue light uses traditional fluorescent triplet-triplet conversion (TTF) technology. This technology has low efficiency but high color purity, and it has basically met the BT.2020 display standards. Green and red light use phosphorescence technology, which has high efficiency, but traditional red phosphorescent materials still have relatively high shoulder peaks, making it relatively difficult to further improve the color gamut display. Therefore, developing a new generation of high color purity red organic electroluminescent materials is crucial.

[0003] Since 2020, red light materials with narrow half-width at half-maximum (WHM < 35nm) based on boron-nitrogen resonant structures have been reported successively, showing outstanding advantages in color purity and further improvements in efficiency. For example, DOI: 10.1039 / D3MH00800B, DOI: 10.1002 / anie.202300934, DOI: 10.1002 / adma.202201442, DOI: 10.1021 / jacs.0c10081, etc., demonstrate the high color purity and efficiency of this type of material, showing great potential as a new generation of red organic electroluminescent materials. However, the development of ultra-high color purity red light materials with boron-nitrogen structures still faces numerous technical challenges. Existing materials also suffer from drawbacks such as insufficient efficiency and lifespan to meet mass production requirements. Developing narrow half-peak red light materials based on boron-nitrogen resonance structures that can meet practical applications is a key technology for next-generation display devices with high color purity, wide color gamut coverage, high efficiency, and high immersion. Furthermore, the structural design of red light materials presents many technical challenges, such as ensuring the material's evaporation temperature, processing window, molecular stability, and other technical indicators while achieving peak values ​​in the red light region, as well as how to achieve more efficient synthesis and production of red light materials.

[0004] In addition, sensitization technology combines triplet exciton sensitizing materials (including but not limited to TADF materials and phosphorescent materials) with fluorescent doping materials. By using triplet exciton sensitizing materials as exciton sensitization media, it fully utilizes triplet excitons and transfers energy to fluorescent doping materials through energy transfer, achieving 100% in-device quantum efficiency (DOI: 10.1038 / ncomms5016, DOI: 10.1038 / s41566-022-00958-4). This technology can compensate for the insufficient exciton utilization of fluorescent doping materials and effectively leverage the high fluorescence quantum yield, high device stability, high color purity, and low cost of fluorescent doping materials, showing broad prospects for OLED applications. For example, CN 107507921A and CN 110492006A disclose a light-emitting layer combination technology using TADF materials with a minimum singlet and triplet energy level difference of less than or equal to 0.2 eV as the main body and boron-containing materials as dopants; CN 110492005A and CN 110492009A disclose a light-emitting layer combination scheme using excitocomplexes as the main body and boron-containing materials as dopants; both can achieve efficiencies comparable to phosphorescence and relatively narrow half-width at half-maximum (HWHM). Therefore, developing sensitization technology based on narrow HWHM boron-containing light-emitting materials has unique advantages and strong potential for improving BT.2020 display performance. Summary of the Invention

[0005] To address the aforementioned problems in the prior art, this invention provides a boron-containing resonant organic compound and an organic electroluminescent device containing the same. The compound of this invention can achieve red light emission.

[0006] The technical solution of the present invention is as follows: a boron-containing resonance organic compound, the structure of which is shown in general formula (1):

[0007]

[0008] In general formula (1), R1 represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or C1 to C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups;

[0009] The occurrence of M1, M2, M3, M5, and M6 being the same or different each time indicates that C6 to C6 are substituted or not substituted by one or more R values. 30 aryl group, C2-C2 substituted or unsubstituted by one or more R groups. 30 One of the heteroaryl groups;

[0010] Ar1 represents C1 to C1, whether substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C3-C, substituted or unsubstituted 30 Silyl groups, substituted or unsubstituted C2-C3 groups 30 Boronyl groups, substituted or unsubstituted C2-C3 groups 30 Thioalkyl groups, C6-C6 substituted or unsubstituted with one or more R groups. 30 aryl group, C2-C2 with or without one or more R-substituted or unsubstituted groups. 30 One of the heteroaryl groups;

[0011] The presence of R, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups;

[0012] Ar1 and M3 are not connected or are connected through connect;

[0013] Y1, Y2, Y3, Y4, Y5, Y6, Y7, and Y8 are each independently represented as C1 to C8 cells with or without substituents. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C3-C, substituted or unsubstituted 30 Silyl groups, substituted or unsubstituted C2-C3 groups 30 Boronyl groups, substituted or unsubstituted C2-C3 groups 30 Thioalkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0014] Y1 and Y2, Y3 and Y4, Y5 and Y6, Y7 and Y8 are either not connected to each other or are connected to form C6 to C6 by one or more Rs, either substituted or unsubstituted. 30 aryl group, C2-C2 with or without one or more R-substituted or unsubstituted groups. 30 Heteroaryl groups, C3-C substituted or unsubstituted with one or more R groups. 10 cycloalkyl;

[0015] X is represented as O, S, N-R0;

[0016] R0 represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a C1-C group that is substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups;

[0017] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 heteroaryl, C2-C 10 alkenyl, C2-C 10 Alkyne group, C1-C 10 Alkoxy, C6~C 10 Any one or more of the aryloxy groups;

[0018] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0019] Furthermore, the structure of the boron-containing resonance organic compound is shown in general formula (1-1):

[0020]

[0021] In general formula (1-1), the definitions of X, R1, M1, M2, M3, M5, M6, Y1, Y2, Y3, Y4, Y5, Y6, Y7, and Y8 are the same as those in general formula (1) above.

[0022] M4 represents C6-C6 substituted or unsubstituted with one or more R groups. 30 aryl group, C2-C2 with or without one or more R-substituted or unsubstituted groups. 30 One of the heteroaryl groups;

[0023] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 heteroaryl, C2-C 10 alkenyl, C2-C 10 Alkyne group, C1-C 10 Alkoxy, C6~C 10 Any one or more of the aryloxy groups;

[0024] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0025] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (2-1) to (2-2):

[0026]

[0027] In general formulas (2-1) to (2-2), the definitions of M5, M6, Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, R1, X, and Ar1 are the same as those in general formula (1) above.

[0028] Each occurrence of Z independently is represented as N, C-(H), or C-(R). a );

[0029] The R a Represented as deuterium atom, halogen atom, cyano group, C1-C with or without substituents. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups;

[0030] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 heteroaryl, C2-C 10 alkenyl, C2-C 10 Alkyne group, C1-C 10 Alkoxy, C6~C 10 Any one or more of aryloxy and arylamino groups;

[0031] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0032] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (3-1) to (3-10):

[0033]

[0034]

[0035] In general formulas (3-1) to (3-10), the definitions of Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, R1, X, and Ar1 are the same as those in general formula (1) above.

[0036] Each occurrence of Z independently is represented as N, C-(H), or C-(R). a );

[0037] The R a Represented as deuterium atom, halogen atom, cyano group, C1-C with or without substituents. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups;

[0038] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 heteroaryl, C2-C10 alkenyl, C2-C 10 Alkyne group, C1-C 10 Alkoxy, C6~C 10 Any one or more of aryloxy and arylamino groups;

[0039] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0040] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (4-1) to (4-13):

[0041]

[0042]

[0043] In general formulas (4-1) to (4-13), the definitions of R1 and X are the same as those in general formula (1) above;

[0044] Each occurrence of Z independently is represented as N, C-(H), or C-(R). a );

[0045] The R a Represented as deuterium atom, halogen atom, cyano group, C1-C with or without substituents. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups;

[0046] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 heteroaryl, C2-C 10 alkenyl, C2-C 10 Alkyne group, C1-C 10 Alkoxy, C6~C 10 Any one or more of aryloxy and arylamino groups;

[0047] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0048] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (5-1) to (5-11):

[0049]

[0050]

[0051] In general formulas (5-1) to (5-11), the definition of R1 is the same as that in general formula (1) above;

[0052] Each occurrence of Z independently is represented as N, C-(H), or C-(R). a );

[0053] The R a Represented as deuterium atom, halogen atom, cyano group, C1-C with or without substituents. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups;

[0054] R2 and R3 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, and C1-C1 atoms substituted or unsubstituted, respectively. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups;

[0055] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 heteroaryl, C2-C 10 alkenyl, C2-C 10 Alkyne group, C1-C 10 Alkoxy, C6~C 10 Any one or more of aryloxy and arylamino groups;

[0056] The heteroatom of the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0057] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (6-1) to (6-3):

[0058]

[0059]

[0060] In general formulas (6-1) to (6-3), the definitions of Y3, Y4, Y5, Y6, R1, X, and Ar1 are the same as those in general formula (1) above;

[0061] Each occurrence of Z independently is represented as N, C-(H), or C-(R). a );

[0062] The Ra Represented as deuterium atom, halogen atom, cyano group, C1-C with or without substituents. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups;

[0063] R'1, R'2, R'3, R'4, R'5, R'6, R'7, R'8, and R'9 are respectively independently represented as a deuterium atom, a halogen atom, a cyano group, and C1-C1 atoms substituted or unsubstituted with substituents. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups;

[0064] m3, m4, m5, m6, m7, and m8 are each independently represented as 0, 1, 2, 3, or 4;

[0065] m1, m2, and m9 can be independently represented as 0, 1, 2, or 3;

[0066] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 heteroaryl, C2-C 10 alkenyl, C2-C 10 Alkyne group, C1-C 10 Alkoxy, C6~C 10 Any one or more of aryloxy and arylamino groups;

[0067] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0068] Further, R1 represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group (substituted or unsubstituted), a methyl group (substituted or unsubstituted), an ethyl group (substituted or unsubstituted), an isopropyl group (substituted or unsubstituted), a tert-butyl group (substituted or unsubstituted), a tert-pentyl group (substituted or unsubstituted), a cyclopentyl group (substituted or unsubstituted), a cyclohexyl group (substituted or unsubstituted), or a phenyl group (substituted or unsubstituted). Diphenyl groups (substituted or unsubstituted), terphenyl groups (substituted or unsubstituted), diphenyl ether groups (substituted or unsubstituted), naphthyl groups (substituted or unsubstituted), anthracene groups (substituted or unsubstituted), phenanthryl groups (substituted or unsubstituted), pyridyl groups (substituted or unsubstituted), quinolinyl groups (substituted or unsubstituted), furanyl groups (substituted or unsubstituted), thiophenyl groups (substituted or unsubstituted), and other substituents. Benzofuranyl, dibenzofuranyl (substituted or unsubstituted), dibenzothiophenyl (substituted or unsubstituted), benzodibenzofuranyl (substituted or unsubstituted), benzodibenzothiophenyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), diphenylfluorenyl (substituted or unsubstituted), and others. One of the following: substituted or unsubstituted spirofluorenyl, substituted or unsubstituted xanthone, substituted or unsubstituted triazine, substituted or unsubstituted methoxy, substituted or unsubstituted tert-butoxy, substituted or unsubstituted diphenylamino, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted indole, and substituted or unsubstituted benzoindole.

[0069] M1, M2, M3, M4, M5, and M6 represent a phenyl group substituted or unsubstituted with one or more Rs, a diphenyl group substituted or unsubstituted with one or more Rs, a terphenyl group substituted or unsubstituted with one or more Rs, a naphthyl group substituted or unsubstituted with one or more Rs, an anthraquinyl group substituted or unsubstituted with one or more Rs, a phenanthryl group substituted or unsubstituted with one or more Rs, a pyridyl group substituted or unsubstituted with one or more Rs, a quinolinyl group substituted or unsubstituted with one or more Rs, a furanyl group substituted or unsubstituted with one or more Rs, a thiophenyl group substituted or unsubstituted with one or more Rs, a benzofuranyl group substituted or unsubstituted with one or more Rs, or a group substituted or unsubstituted with one or more Rs. One of the following: substituted dibenzofuranyl, dibenzothiophenylyl (substituted or unsubstituted with one or more Rs), carbazoyl (substituted or unsubstituted with one or more Rs), N-phenylcarbazoyl (substituted or unsubstituted with one or more Rs), 9,9-dimethylfluorenyl (substituted or unsubstituted with one or more Rs), spirofluorenyl (substituted or unsubstituted with one or more Rs), xanthoneyl (substituted or unsubstituted with one or more Rs), triazineyl (substituted or unsubstituted with one or more Rs), 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl (substituted or unsubstituted with one or more Rs), indoleyl (substituted or unsubstituted with one or more Rs), and benzoindoleyl (substituted or unsubstituted with one or more Rs).

[0070] The R, R aR'1, R'2, R'3, R'4, R'5, R'6, R'7, R'8, and R'9 are independently represented as a deuterium atom, a halogen atom, a cyano group, an adamantyl group (substituted or unsubstituted), a methyl group (substituted or unsubstituted), an ethyl group (substituted or unsubstituted), an isopropyl group (substituted or unsubstituted), a tert-butyl group (substituted or unsubstituted), a tert-pentyl group (substituted or unsubstituted), a cyclopentyl group (substituted or unsubstituted), and a group substituted or... Unsubstituted cyclohexyl, phenyl groups substituted or unsubstituted, diphenyl groups substituted or unsubstituted, terphenyl groups substituted or unsubstituted, diphenyl ether groups substituted or unsubstituted, naphthyl groups substituted or unsubstituted, anthraquinyl groups substituted or unsubstituted, phenanthryl groups substituted or unsubstituted, pyridyl groups substituted or unsubstituted, quinolinyl groups substituted or unsubstituted, furanyl groups substituted or unsubstituted, and other substituents. Thiophene group, benzofuran group (substituted or unsubstituted), dibenzofuran group (substituted or unsubstituted), dibenzothiophene group (substituted or unsubstituted), benzodibenzofuran group (substituted or unsubstituted), benzodibenzothiophene group (substituted or unsubstituted), carbazolyl group (substituted or unsubstituted), N-phenylcarbazolyl group (substituted or unsubstituted), 9,9-dimethylfluorenyl group (substituted or unsubstituted), diphenylfluorene group (substituted or unsubstituted) One of the following: spirofluorenyl (substituted or unsubstituted), xanthone (substituted or unsubstituted), triazine (substituted or unsubstituted), methoxy (substituted or unsubstituted), tert-butoxy (substituted or unsubstituted), diphenylamino (substituted or unsubstituted), 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl (substituted or unsubstituted), indolyl (substituted or unsubstituted), and benzoindolyl (substituted or unsubstituted).

[0071] R0, R2, and R3 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, adamantyl group (substituted or unsubstituted), methyl group (substituted or unsubstituted), ethyl group (substituted or unsubstituted), isopropyl group (substituted or unsubstituted), tert-butyl group (substituted or unsubstituted), tert-pentyl group (substituted or unsubstituted), cyclopentyl group (substituted or unsubstituted), cyclohexyl group (substituted or unsubstituted), and [other groups are not specified in the original text]. Phenyl, diphenyl (substituted or unsubstituted), triphenyl (substituted or unsubstituted), diphenyl ether (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraquinyl (substituted or unsubstituted), phenanthryl (substituted or unsubstituted), pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), and so on. Unsubstituted benzofuranyl, dibenzofuranyl (substituted or unsubstituted), dibenzothiophenyl (substituted or unsubstituted), benzodibenzofuranyl (substituted or unsubstituted), benzodibenzothiophenyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), diphenylfluorenyl (substituted or unsubstituted), and so on. One of the following: substituted or unsubstituted spirofluorenyl, substituted or unsubstituted xanthone, substituted or unsubstituted triazine, substituted or unsubstituted methoxy, substituted or unsubstituted tert-butoxy, substituted or unsubstituted diphenylamino, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted indole, and substituted or unsubstituted benzoindole.

[0072] Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, and Ar1 represent: adamantyl (substituted or unsubstituted), methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), tert-pentyl (substituted or unsubstituted), cyclopentyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), and [other compounds, substituted or unsubstituted]. Phenyl, diphenyl (substituted or unsubstituted), triphenyl (substituted or unsubstituted), diphenyl ether (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraquinyl (substituted or unsubstituted), phenanthryl (substituted or unsubstituted), pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), and so on. Substituted benzofuranyl, dibenzofuranyl (substituted or unsubstituted), dibenzothiophenyl (substituted or unsubstituted), benzodibenzofuranyl (substituted or unsubstituted), benzodibenzothiophenyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), diphenylfluorenyl (substituted or unsubstituted), and so on. One of the following: substituted or unsubstituted spirofluorenyl, substituted or unsubstituted xanthone, substituted or unsubstituted triazine, substituted or unsubstituted methoxy, substituted or unsubstituted tert-butoxy, substituted or unsubstituted diphenylamino, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted indole, and substituted or unsubstituted benzoindole.

[0073] The substituents used for the substituent groups are selected from deuterium, chlorine, fluorine, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, phenyl, diphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiophene, indoleyl, pyrroleyl, and dibenzofuranyl. Dibenzothiophene, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, azirphenanthrenel, diphenylamino, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, benzoindolyl, deuterated adamantyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated tert-amyl, deuterated tert-butyl, deuterated... Butyl, deuterated phenyl, deuterated diphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated pyridazinyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated quinoxalinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated furanyl, deuterated thiopheneyl, deuterated indole One or more of the following: dolomyl, deuterated pyrroleyl, deuterated dibenzofuranyl, deuterated dibenzothiopheneyl, deuterated 9,9-dimethylfluorenyl, deuterated spirofluorenyl, deuterated carbazolyl, deuterated N-phenylcarbazolyl, deuterated carbazolinyl, deuterated azirophenonel, deuterated 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and deuterated benzoindolyl.

[0074] Preferably, R1 represents hydrogen atom, deuterium atom, halogen atom, cyano, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl The following are substituted phenyl groups: methyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boraneyl, methoxy, tert-butoxy, and diphenylamino.

[0075] M1, M2, M3, M4, M5, and M6 represent phenyl, diphenyl, deuterated diphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, and tert-butyl-substituted phenyl. One of the following: methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, oxanthoneyl, and phenyl-substituted triazineyl;

[0076] The R, R aR'1, R'2, R'3, R'4, R'5, R'6, R'7, R'8, and R'9 are independently represented as deuterium atom, halogen atom, cyano group, adamantyl group, methyl group, deuterated methyl group, trifluoromethyl group, ethyl group, deuterated ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, cyclopentyl group, deuterated cyclopentyl group, methyl-substituted cyclopentyl group, and cyclohexyl group, respectively. Phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, 9,9-dimethylfluorenyl, spirofluorenyl One of the following: methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boraneyl, methoxy, tert-butoxy, and diphenylamino.

[0077] R0, R2, and R3 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, 9,9-dimethylfluorenyl, spirofluorenyl, and methyl-substituted phenyl. One of the following: ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boronyl, methoxy, and tert-butoxy.

[0078] Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, and Ar1 represent adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, 9,9-dimethylfluorenyl, and spirofluorenyl. One of the following: methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, and phenyl-substituted triazineyl;

[0079] The substituents used for the substituent groups are selected from one or more of the following: deuterium, chlorine, fluorine, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

[0080] Preferably, the M1 and M4 rings are represented by the following groups:

[0081] any one of them;

[0082] The M2 and M3 rings are represented by the following groups:

[0083] any one of them;

[0084] The M5 and M6 rings are independently represented by the following ring structures:

[0085]

[0086] any one of them;

[0087] Each occurrence of Z, whether the same or different, is represented by N, C-(H), or CR. a ;

[0088] The R a R, R'1, R'2, R'3, R'4, R'5, R'6, R'7, R'8, and R'9 can be independently represented as shown in the following structures:

[0089] Cyano, deuterium, methyl, ethyl, isopropyl, tert-butyl

[0090] Any one of them;

[0091] R1 is represented by the following structure:

[0092] Hydrogen atom, cyano group, deuterium atom, methyl group, ethyl group, isopropyl group, tert-butyl group

[0093]

[0094] Any one of them;

[0095] Ar1, R0, R2, R3, Y1, Y2, Y3, Y4, Y5, Y6, Y7, and Y8 are each independently represented by the following structures:

[0096]

[0097] Any one of the following. Furthermore, the specific structural formula of the boron-containing resonance organic compound is any one of the following structures:

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] The present invention also provides an organic light-emitting device, comprising a substrate, a first electrode, an organic functional material layer, and a second electrode, wherein the first electrode is located on the substrate, the organic functional material layer is located on the first electrode, the second electrode is located on the organic functional material layer, and the organic functional material layer contains the boron-containing resonant organic compound of the present invention.

[0120] Preferably, the organic functional material layer includes a light-emitting layer, and the light-emitting layer contains the boron-containing resonant organic compound of the present invention;

[0121] Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the dopant material is the boron-containing resonant organic compound of the present invention.

[0122] Furthermore, the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material. The exciton-sensitizing material is a complex containing a metal element, and the dopant material is the boron-containing resonant organic compound described in this invention.

[0123] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0124] 1) The compounds of this invention can be used in organic electroluminescent devices as dopants for the light-emitting layer. They can emit red fluorescence under an electric field and can be applied in OLED lighting or OLED display fields.

[0125] 2) The compounds of this invention have a narrower FWHM spectrum, which can effectively improve the color gamut of the device.

[0126] 3) The compounds of the present invention can achieve higher efficiency in top-emitting devices. Attached Figure Description

[0127] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device using the materials listed in this invention;

[0128] In this structure, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is an electron transport layer, 8 is an electron injection layer, and 9 is a cathode layer. Detailed Implementation

[0129] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0130] In this invention, the terms "upper," "lower," "top," and "bottom," used to describe electrodes, organic electroluminescent devices, and other structures, indicate orientation only in a specific state and do not imply that the structure can only exist in that orientation. Conversely, if the structure can be repositioned, such as by inverting it, the orientation of the structure changes accordingly. Specifically, in this invention, the "bottom" or "lower" side of the electrode refers to the side of the electrode closer to the substrate during fabrication, while the opposite side farther from the substrate is the "top" or "upper" side.

[0131] In this invention, the substituted or unsubstituted aromatic amino group refers to... Wherein Q1 and Q2 represent aromatic groups that are substituted or unsubstituted, and Q1 and Q2 preferably represent C6-C6 groups that are substituted or unsubstituted. 30 The aryl group may be substituted or unsubstituted at C2-C2. 30 Mixed aromatic compounds.

[0132] In this invention, the C3-C groups, whether substituted or unsubstituted, are... 30 Silyl refers to Where Q3, Q4, and Q5 represent C1 to C2 cells that are substituted or unsubstituted. 10 Alkyl groups or C3-C6 groups substituted or unsubstituted 10 Cycloalkyl.

[0133] In this invention, the C2-C groups, whether substituted or unsubstituted, are... 30 Boronyl refers to Q6 and Q7 represent C1-C cells that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkyl, C6-C6 substituted or unsubstituted 30 Aryl, substituted or unsubstituted C2-C 30 Mixed aromatic compounds.

[0134] In this invention, the C6-C6 groups, whether substituted or unsubstituted, are... 30Aryl refers to an aryl group with 6 to 30 carbon atoms, substituted or unsubstituted, preferably an aryl group with 6 to 18 carbon atoms, preferably an aryl group with 6 to 12 carbon atoms, preferably a phenyl group, a naphthyl group, a diphenyl group, a terphenyl group, anthracene group, a phenanthrene group, a dimethylfluorenyl group, a diphenylfluorenyl group, a spirofluorenyl group, a tetraphenyl group, a pyrene group, or a pyrene group. The group may contain, but is not limited to, a triphenylene group substituted or unsubstituted with a substituent, a perylene group substituted or unsubstituted with a substituent, an indene group substituted or unsubstituted with a substituent, a 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group substituted or unsubstituted with a substituent, a combination thereof, or a fused ring of the aforementioned groups.

[0135] In this invention, C6 to C 30 Aryl refers to an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 18 carbon atoms, and even more preferably an aryl group having 6 to 12 carbon atoms. Other preferred aryl groups include phenyl, naphthyl, diphenyl, terphenyl, anthracene, phenanthrene, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, condensed tetraphenyl, and pyrene. Fused rings of methyl, triphenyl, peryl, indole, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, combinations thereof, or combinations of the foregoing groups, but not limited thereto.

[0136] In this invention, the deuterium-substituted C6 to C6 are... 30 Aryl refers to a deuterated aryl group having 6 to 30 carbon atoms, preferably a deuterated aryl group having 6 to 18 carbon atoms, preferably a deuterated aryl group having 6 to 12 carbon atoms, preferably a deuterated phenyl, deuterated naphthyl, deuterated diphenyl, deuterated terphenyl, deuterated anthracene, deuterated phenanthyl, deuterated dimethylfluorenyl, deuterated diphenylfluorenyl, deuterated spirofluorenyl, deuterated tetraphenyl, deuterated pyrene, or deuterated... The group may contain, but is not limited to, deuterated triphenylene, deuterated perylene, deuterated indene, deuterated 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, combinations thereof, or fused rings of the aforementioned groups.

[0137] In this invention, the C2-C groups, whether substituted or unsubstituted, are... 30A heteroaryl group refers to a heteroaryl group with 2 to 30 carbon atoms, substituted or unsubstituted, preferably a heteroaryl group with 2 to 20 carbon atoms, preferably a heteroaryl group with 4 to 20 carbon atoms, preferably a heteroaryl group with 4 to 12 carbon atoms, preferably a heteroaryl group with 5 to 12 carbon atoms, preferably a furanyl group, a thiophene group, a pyrrole group, or a group substituted or unsubstituted with a substituent. Unsubstituted pyrazolyl group, imidazolyl group substituted or unsubstituted, triazolyl group substituted or unsubstituted, oxazolyl group substituted or unsubstituted, thiazolyl group substituted or unsubstituted, oxadiazolyl group substituted or unsubstituted, thiadiazolyl group substituted or unsubstituted, pyridyl group substituted or unsubstituted, pyrimidinyl group substituted or unsubstituted, pyrazinyl group substituted or unsubstituted, triazinyl group substituted or unsubstituted, benzofuranyl group substituted or unsubstituted, benzothiophenyl group substituted or unsubstituted, and other substituents. Substituted or unsubstituted benzimidazolyl, indolyl substituted or unsubstituted, quinolinyl substituted or unsubstituted, isoquinolinyl substituted or unsubstituted, quinazolinyl substituted or unsubstituted, quinoxolinyl substituted or unsubstituted, quinoxolinyl substituted or unsubstituted, naphthidyl substituted or unsubstituted, benzoxazinyl substituted or unsubstituted, benzothiazinyl substituted or unsubstituted, benzopyrimidinyl substituted or unsubstituted, acridineyl substituted or unsubstituted, substituted or unsubstituted The following are fused rings, including but not limited to: substituted phenazinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fumonyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted benzodibenzofuranyl, substituted or unsubstituted benzodibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted benzoindolyl, combinations thereof, or combinations of the foregoing groups.

[0138] In this invention, C2 to C 30The heteroaryl group refers to a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 20 carbon atoms, more preferably a heteroaryl group having 4 to 20 carbon atoms, more preferably a heteroaryl group having 4 to 12 carbon atoms, more preferably a heteroaryl group having 5 to 12 carbon atoms, and preferably furanyl, thiopheneyl, pyrroleyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, triazinyl, or benzofuranyl. Benzothiophene, benzimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinolinyl, quinoxolinyl, naphridinyl, benzoxazinyl, benzothiazinyl, benzopyrimidinyl, acridineyl, phenazinyl, phenthiazinyl, phenoxazinyl, fumonyl, dibenzofuranyl, dibenzothiophene, benzodibenzofuranyl, benzodibenzothiophene, carbazoyl, N-phenylcarbazoyl, benzoindolyl, and combinations thereof or combinations of the foregoing groups, but not limited thereto.

[0139] In this invention, the deuterium-substituted C2-C 30 The heteroaryl group refers to a heteroaryl group with 2 to 30 deuterated carbon atoms, preferably a heteroaryl group with 2 to 20 deuterated carbon atoms, preferably a heteroaryl group with 4 to 12 deuterated carbon atoms, preferably a heteroaryl group with 5 to 12 deuterated carbon atoms, preferably a deuterated furanyl, deuterated thiophene, deuterated pyrrole, deuterated pyrazolyl, deuterated imidazolyl, deuterated triazolyl, deuterated oxazolyl, deuterated thiazolyl, deuterated oxadiazolyl, deuterated thiadiazolyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated triazinyl, deuterated benzofuranyl, deuterated benzothiophene, or deuterated benzimidazolyl. Deuterated indolyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated quinazolinyl, deuterated quinolinyl, deuterated quinoxalinyl, deuterated naphthidyl, deuterated benzoxazinyl, deuterated benzothiazinyl, deuterated benzopyrimidinyl, deuterated acridineyl, deuterated benzazinyl, deuterated benzathiazinyl, Deuterated phenoxazinyl, deuterated fumonyl, deuterated dibenzofuranyl, deuterated dibenzothiophenyl, deuterated benzodibenzofuranyl, deuterated benzodibenzothiophenyl, deuterated carbazoyl, deuterated substituted N-phenylcarbazoyl, deuterated benzoindolyl, combinations thereof, or fused rings of the foregoing groups, but not limited thereto.

[0140] In this invention, the number of heteroatoms in the heteroaryl group is 1-5, preferably 1-4, preferably 1-3, preferably 1-2, and preferably 1.

[0141] In this invention, the C1-C1 groups, whether substituted or unsubstituted, are... 10Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to an alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted, preferably an alkyl group having 1 to 6 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, preferably methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, etc., substituted or unsubstituted. Isobutyl, sec-butyl (substituted or unsubstituted), neopentyl (substituted or unsubstituted), n-pentyl (substituted or unsubstituted), isopentyl (substituted or unsubstituted), tert-pentyl (substituted or unsubstituted), octyl (substituted or unsubstituted), heptyl (substituted or unsubstituted), n-decyl (substituted or unsubstituted), 1-methylpentyl (substituted or unsubstituted), 2-methylpentyl (substituted or unsubstituted), 3-methylpentyl (substituted or unsubstituted), 1-butylpentyl (substituted or unsubstituted), 2-methylbutyl (substituted or unsubstituted), etc., but not limited to these.

[0142] In this invention, C1 to C 10 Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 6 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, preferably methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, tert-pentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, 2-methylbutyl, etc., but not limited to these.

[0143] In this invention, the deuterium-substituted C1 to C1 are... 10 Alkyl groups (including straight-chain alkyl groups and branched alkyl groups) refer to deuterated alkyl groups having 1 to 10 carbon atoms, preferably deuterated alkyl groups having 1 to 6 carbon atoms, preferably deuterated alkyl groups having 1 to 5 carbon atoms, preferably deuterated alkyl groups having 1 to 4 carbon atoms, preferably deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, or deuterated tert-butyl. Butyl, deuterium-substituted isobutyl, deuterium-substituted sec-butyl, deuterium-substituted neopentyl, deuterium-substituted n-pentyl, deuterium-substituted isopentyl, deuterium-substituted tert-pentyl, deuterium-substituted octyl, deuterium-substituted heptyl, deuterium-substituted n-decyl, deuterium-substituted 1-methylpentyl, deuterium-substituted 2-methylpentyl, deuterium-substituted 3-methylpentyl, deuterium-substituted 1-butylpentyl, deuterium-substituted 2-methylbutyl, etc., but not limited to these.

[0144] In this invention, the C2-C groups, whether substituted or unsubstituted, are... 10 The alkynyl group refers to an alkynyl group having 2 to 10 carbon atoms substituted or unsubstituted by a substituent, preferably an alkynyl group having 2 to 6 carbon atoms substituted or unsubstituted by a substituent, preferably an alkynyl group having 2 to 5 carbon atoms substituted or unsubstituted by a substituent, preferably an alkynyl group having 2 to 4 carbon atoms substituted or unsubstituted by a substituent, preferably an ethynyl group substituted or unsubstituted by a substituent, a propynyl group substituted or unsubstituted by a substituent, a 1-propynyl group substituted or unsubstituted by a substituent, a 1-butynyl group substituted or unsubstituted by a substituent, a 2-butynyl group substituted or unsubstituted by a substituent, a 3-methyl-1-propynyl group substituted or unsubstituted by a substituent, etc., but is not limited thereto.

[0145] In this invention, the C3-C groups, whether substituted or unsubstituted, are... 10 Cycloalkyl refers to monocyclic or polycyclic alkyl groups comprising 3 to 10 cyclic atoms, with or without substituted substituents, where the rings can be linked by single bonds or cyclic fusion. In this document, C4-C6 alkyl groups, with or without substituted substituents, are preferred. 10 Cycloalkyl groups, more preferably C5-C6 substituted or unsubstituted, are preferred. 10 Cycloalkyl groups, non-limiting examples of which may include cyclopropyl groups substituted or unsubstituted with substituents, cyclobutyl groups substituted or unsubstituted with substituents, cyclopentyl groups substituted or unsubstituted with substituents, cyclohexyl groups substituted or unsubstituted with substituents, 4-methylcyclohexyl groups substituted or unsubstituted with substituents, 4,4-dimethylcyclohexyl groups substituted or unsubstituted with substituents, adamantyl groups substituted or unsubstituted with substituents, cycloheptyl groups substituted or unsubstituted with substituents, etc., but are not limited thereto.

[0146] In this invention, C3 to C 10 Cycloalkyl refers to a monocyclic or polycyclic alkyl group comprising 3 to 10 cyclic atoms, with the rings linked by single bonds or cyclic fusion. In this document, C4-C is preferred. 10 Cycloalkyl, more preferably C5-C 10 Cycloalkyl groups, non-limiting examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl, but are not limited thereto.

[0147] In this invention, the deuterium-substituted C3-C 10Cycloalkyl refers to a deuterium-substituted monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, deuterium-substituted C4-C9 cycloalkyl groups are preferred, more preferably C5-C8 cycloalkyl groups, and particularly preferably C5-C7 cycloalkyl groups. Non-limiting examples may include, but are not limited to, deuterium-substituted cyclopropyl, deuterium-substituted cyclobutyl, deuterium-substituted cyclopentyl, deuterium-substituted cyclohexyl, deuterium-substituted 4-methylcyclohexyl, deuterium-substituted 4,4-dimethylcyclohexyl, deuterium-substituted adamantyl, and deuterium-substituted cycloheptyl.

[0148] In this invention, the halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0149] In this invention, the C1-C1 groups, whether substituted or unsubstituted, are... 10 Alkoxy groups include, but are not limited to, methoxy groups substituted or unsubstituted with substituents, ethoxy groups substituted or unsubstituted with substituents, propoxy groups substituted or unsubstituted with substituents, butoxy groups substituted or unsubstituted with substituents, pentoxy groups substituted or unsubstituted with substituents, hexoxy groups substituted or unsubstituted with substituents, or isopropoxy groups substituted or unsubstituted with substituents.

[0150] In this invention, the C2-C groups, whether substituted or unsubstituted, are... 10 Alkenyl refers to vinyl groups that are substituted or unsubstituted with substituents, allyl groups that are substituted or unsubstituted with substituents, 1-butenyl groups that are substituted or unsubstituted with substituents, 2-butenyl groups that are substituted or unsubstituted with substituents, 3-butenyl groups that are substituted or unsubstituted with substituents, 1,3-butadienyl groups that are substituted or unsubstituted with substituents, 1-methyl vinyl groups that are substituted or unsubstituted with substituents, styryl groups that are substituted or unsubstituted with substituents, 2,2-diphenyl vinyl groups that are substituted or unsubstituted with substituents, 1,2-diphenyl vinyl groups that are substituted or unsubstituted with substituents, and others. Substituted or unsubstituted 1,1-dimethylallyl, 1-methylallyl substituted or unsubstituted by a substituent, 2-methylallyl substituted or unsubstituted by a substituent, 1-phenylallyl substituted or unsubstituted by a substituent, 2-phenylallyl substituted or unsubstituted by a substituent, 3,3-diphenylallyl substituted or unsubstituted by a substituent, 1,2-dimethylallyl substituted or unsubstituted by a substituent, 1-phenyl-1-butenyl substituted or unsubstituted by a substituent, and 3-phenyl-1-butenyl substituted or unsubstituted by a substituent, etc., but not limited thereto.

[0151] In this invention, the substituents are selected from deuterium, chlorine, fluorine, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiophene, indoleyl, pyrroleyl, and dibenzofuranyl. Dibenzothiophene, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, azirphenanthrenel, diphenylamino, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, benzoindolyl, deuterated adamantyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated tert-amyl, deuterated tert-butyl, deuterated... Butyl, deuterated phenyl, deuterated diphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated pyridazinyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated quinoxalinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated furanyl, deuterated thiopheneyl, deuterated indole One or more of the following: indole, deuterated pyrrole, deuterated dibenzofuranyl, deuterated dibenzothiopheneyl, deuterated 9,9-dimethylfluorenyl, deuterated spirofluorenyl, deuterated carbazolyl, deuterated N-phenylcarbazolyl, deuterated carbazolinyl, deuterated azephenanthyl, deuterated 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and deuterated benzoindole.

[0152] As the substrate for the organic electroluminescent device of this invention, any substrate commonly used in organic electroluminescent devices can be used. Examples include transparent substrates, such as glass or transparent PI film substrates; and opaque substrates, such as silicon substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Their application varies depending on their properties. In this invention, a transparent glass substrate is preferred. There are no particular limitations on the thickness of the substrate.

[0153] A first electrode is formed on a substrate, and the first electrode and a second electrode may be opposite each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include metals such as Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, or Cr, or it may be an alloy of several metals, or a combination of metals, metal oxides, or metal alloys. The thickness of the first electrode layer depends on the material used, and is typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0154] The organic functional material layer disposed between the first electrode and the second electrode includes, from bottom to top, a hole transport region, a light-emitting layer, and an electron transport region.

[0155] In this invention, the hole transport region constituting the organic electroluminescent device can be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0156] As for the materials used in the hole injection layer, hole transport layer, and electron blocking layer, any material can be selected from known materials used in organic electroluminescent devices.

[0157] The hole injection layer comprises a host organic material capable of conducting holes, and a p-type doped material with a deep HOMO level (correspondingly, a deep LUMO level). Based on empirical observations, to achieve smooth hole injection from the anode to the organic film, the HOMO level of the host organic material used in the anode interface buffer layer must possess certain characteristics with the p-doped material. This is necessary to enable charge transfer states between the host and doped materials, achieve ohmic contact between the buffer layer and the anode, and realize efficient hole injection conduction from the electrode to the hole injection layer.

[0158] Based on the above empirical summary, for hole-based host organic materials with different HOMO energy levels, it is necessary to select different P-doped materials to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0159] Preferably, the main organic material used as the hole injection layer of the present invention may be selected from the following prior art:

[0160] The compounds disclosed in WO2017191896A1, JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, and CN105439999A, but not limited thereto.

[0161] Preferably, the p-type doped material is a charge-conducting compound disclosed in the prior art. The p-type dopant can be selected from compounds disclosed in any of the following documents: WO2011073149A, EP1968131A1, EP2276085A1, EP2213662A1, EP1722602A1, EP2045848A1, DE10200703122. 0A1, US20100181555A1, US20100102709A1, WO2009003455A1, WO2010094378A1, WO2011120709A1, US20100096600A1, DE102012209523A1, CN101728485A and WO2012095143A1, but not limited to these.

[0162] In one embodiment of the invention, the hole injection layer comprises a p-type dopant material selected from the following charge-conducting materials: quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ); or hexaazatriphenyl derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenyl (HAT-CN); or cyclopropane derivatives, such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0163] In the hole injection layer of the present invention, the ratio of hole transport material to P-type doped material is 99:1-95:5, preferably 99:1-97:3, based on mass.

[0164] The thickness of the hole injection layer of the present invention can be 5-100 nm, preferably 5-50 nm, and more preferably 5-20 nm, but the thickness is not limited to this range.

[0165] Preferably, the hole transport layer material of the present invention may be selected from the compounds disclosed in the prior art:

[0166]

[0167] Preferably, the main organic material used as the hole transport layer material and the hole injection layer of the present invention is selected from the same compound.

[0168] The thickness of the hole transport layer of the present invention can be 5-200 nm, preferably 10-150 nm, and more preferably 20-120 nm, but the thickness is not limited to this range.

[0169] In one embodiment of the present invention, the electron blocking layer material may be selected from the compounds disclosed in the prior art:

[0170]

[0171]

[0172] The thickness of the electron blocking layer of this invention can be 1-100 nm, but the thickness is not limited to this range.

[0173] After forming the hole injection layer, hole transport layer, and electron blocking layer, a corresponding light-emitting layer is formed on top of the electron blocking layer.

[0174] The light-emitting layer may include a host material and a dopant material. The host material may be a red light host material commonly used in the art, and the dopant material may be a boron-containing resonant organic compound represented by the general formula (1) of this invention.

[0175] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material is 99:1-70:30, preferably 99:1-85:15 and more preferably 98:2-87:13, based on mass.

[0176] The thickness of the light-emitting layer can be adjusted to optimize luminous efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and even more preferably 15-40 nm, but the thickness is not limited to this range.

[0177] In this invention, the electron transport region may include, from bottom to top, an electron transport layer and an electron injection layer disposed on the light-emitting layer, but is not limited thereto.

[0178] An electron transport layer may be disposed above the light-emitting layer. The electron transport layer material is one that readily receives electrons from the cathode and transfers these electrons to the light-emitting layer. Preferably, a material with high electron mobility is used. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials disclosed in the prior art for organic electroluminescent devices can be used, for example:

[0179]

[0180] In a preferred embodiment of the invention, the electron transport layer further includes other compounds conventionally used in electron transport layers, such as Alq3, Liq, preferably Liq.

[0181] The thickness of the electron transport layer of the present invention can be 10-80 nm, preferably 20-60 nm and more preferably 25-45 nm, but the thickness is not limited to this range.

[0182] An electron injection layer can be disposed above the electron transport layer. The electron injection layer material is typically preferably a material with a low work function, which facilitates electron injection into the organic functional material layer. As the electron injection layer material for the organic electroluminescent device of this invention, electron injection layer materials disclosed in the prior art for organic electroluminescent devices can be used, such as LiF, Cs₂CO₃, CsF, Csq, NaF, MgF₂, CaF₂, Al₂O₃, Yb, etc.

[0183] The thickness of the electron injection layer of the present invention can be 0.1-5 nm, preferably 0.5-3 nm and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[0184] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmission electrode, a semi-transmission electrode, or a reflection electrode. When the second electrode is a transmission electrode, it may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF2, Ba, Ag, or compounds or mixtures thereof; when the second electrode is a semi-transmission electrode or a reflection electrode, it may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0185] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can; or a thin film covering the entire surface of the organic layer.

[0186] The method for preparing the organic electroluminescent device of the present invention includes sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, onto a substrate. For this purpose, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI can be used, but are not limited thereto. In the present invention, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.

[0187] Synthesis Examples

[0188] All raw materials involved in the synthesis embodiments of the present invention can be purchased from the market or obtained by conventional preparation methods in the art;

[0189]

[0190] Synthesis of intermediate C-1: Starting material B-1 (2.36 g, 8 mmol) was dissolved in 45 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 4.7 mL of n-butyllithium (2.5 M, 11.7 mmol) n-hexane solution was slowly added. After stirring at -78 °C for 3.5 hours, 30 mL of tetrahydrofuran solution of starting material A-1 (1.44 g, 8 mmol) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 30 mL of dilute hydrochloric acid (1.0 M), distilled water, and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and then slowly quenched with an aqueous solution of sodium bicarbonate (NaHCO3). Next, the aqueous layer was separated, extracted with dichloromethane, dried with sodium sulfate, filtered, distilled under reduced pressure, and passed through a column to obtain intermediate C-1.

[0191] Synthesis of intermediate E-1: Intermediate C-1 (2.65 g, 8 mmol), starting material D-1 (2.61 g, 8 mmol), Pd2(dba)3 (0.5 mmol, 0.46 g), tri-tert-butylphosphine tetrafluoroborate (1 mmol, 0.29 g), sodium tert-butoxide (30 mmol, 2.88 g), and toluene (160 mL) were added to a two-necked flask. The mixture was heated under reflux for 25 hours under nitrogen protection. After the reaction system cooled to room temperature, the reaction mixture was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate E-1.

[0192]

[0193] The synthesis of intermediate C-2 is similar to that of intermediate C-1, except that raw material A-2 is used instead of raw material A-1.

[0194] The synthesis of intermediate E-2 is similar to that of intermediate E-1, except that intermediate C-1 is replaced by intermediate C-2.

[0195]

[0196] The synthesis of intermediate C-3 is similar to that of intermediate C-1, except that raw material A-3 is used instead of raw material A-1.

[0197] The synthesis of intermediate E-3 is the same as that of intermediate E-1, except that intermediate C-1 is replaced by intermediate C-3.

[0198]

[0199] Synthesis of intermediate C-4: Under nitrogen protection, in a round-bottom flask, raw material A-4 (9.49 g, 30 mmol), raw material B-4 (11.89 g, 30 mmol), K2CO3 (13.82 g, 100 mmol), tetrahydrofuran (210 mL), and water (60 mL) were added sequentially. Nitrogen gas was purged for 60 min to replace the air. Pd(PPh3)4 (0.69 g, 0.6 mmol) was added, and the mixture was heated under reflux for 16 h under nitrogen protection. TCL analysis of the reaction solution showed that the reactant A-4 reacted completely. After the reaction was completed, the reaction system was naturally cooled to room temperature, the solvent was removed by rotary evaporation, the residue was dissolved in 150 ml of dichloromethane, washed with 120 ml of water, poured into a separatory funnel, shaken, and allowed to stand for separation. The aqueous phase was extracted with dichloromethane (60 ml * 3), the organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the filtrate was removed by rotary evaporation to obtain the crude product. The crude product was purified by silica gel column chromatography to obtain intermediate C-4.

[0200] The synthesis of intermediate E-4 is the same as that of intermediate E-1, except that intermediate C-4 is used to replace raw material D-1.

[0201]

[0202] The synthesis of intermediate E-5 is the same as that of intermediate E-1, except that intermediate C-1 is replaced by raw material B-5.

[0203]

[0204] The synthesis of intermediate E-6 is the same as that of intermediate E-1, except that intermediate C-1 is replaced by raw material B-6.

[0205]

[0206] Synthesis of intermediate G-1: Starting material F-1 (1.10 g, 10 mmol), intermediate E-1 (12.69 g, 22 mmol), CuI (0.5 mmol, 0.10 g), potassium carbonate (62.5 mmol, 8.64 g), and DMSO (60 mL) were added to a two-necked flask. The mixture was then stirred in an oil bath at 110 °C for 20 hours. After the reaction mixture cooled to room temperature, it was filtered through a silica gel pad and then concentrated under vacuum. The crude product was further purified by column chromatography and dried under vacuum to obtain intermediate G-1.

[0207] Synthesis of Compound 1: In a three-necked flask under nitrogen protection, intermediate G-1 (10 mmol, 11.02 g) and 140 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (36 mmol, 14.4 mL) was added at -78 °C, the system was heated to 68 °C and reacted for 8.5 h. Then, boron tribromide (30 mmol, 3 mL) was added at 0 °C, and the reaction was continued at room temperature for 7.5 h. Next, N,N-diisopropylethylamine (40 mmol, 7 mL) was added at 0 °C, the system was heated to 210 °C and reacted for 18 h. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate H-1 and compound 1. Compound 1 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width of the M peak was 24 nm, obtained by measuring the fluorescence spectrometer of the Horiba Fluorolog-3 series.

[0208]

[0209] The synthesis of intermediate G-2 is similar to that of intermediate G-1, except that raw material F-1 is replaced by raw material F-2.

[0210] The synthesis of compound 9 is similar to that of compound 1, except that intermediate G-1 is replaced by intermediate G-2. Compound 9 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the M peak was 24 nm, obtained by measuring the fluorescence spectrometer of the Horiba Fluorolog-3 series.

[0211]

[0212] The synthesis of intermediate G-3 is the same as that of intermediate G-1, except that raw material F-2 is used to replace raw material F-1, and intermediate E-4 is used to replace intermediate E-1.

[0213] The synthesis of compound 11 is the same as that of compound 1, except that intermediate G-1 is replaced by intermediate G-3. Compound 11 is synthesized in toluene solution (1×10⁻⁶). -5The half-width of the peak (M) was 25 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0214]

[0215] The synthesis of intermediate G-4 is the same as that of intermediate G-1, except that raw material F-2 is used to replace raw material F-1, and intermediate E-2 is used to replace intermediate E-1.

[0216] The synthesis of compound 49 is similar to that of compound 1, except that intermediate G-1 is replaced by intermediate G-4. Compound 49 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the peak (M) was 25 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0217]

[0218] The synthesis of intermediate G-5 is the same as that of intermediate G-1, except that raw material F-2 is used to replace raw material F-1, and intermediate E-3 is used to replace intermediate E-1.

[0219] The synthesis of compound 81 is similar to that of compound 1, except that intermediate G-1 is replaced by intermediate G-5. Compound 81 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the M peak was 24 nm, obtained by measuring the fluorescence spectrometer of the Horiba Fluorolog-3 series.

[0220]

[0221] The synthesis of intermediate G-6 is similar to that of intermediate G-1, except that raw material F-2 is used instead of raw material F-1. In the synthesis of intermediate G-6, the feed ratio of raw material F-2 and intermediate E-1 is 1:1.

[0222] The synthesis of intermediate H-6 is similar to that of intermediate G-1, except that intermediate G-6 replaces raw material F-1, and intermediate E-5 replaces intermediate E-1. In the synthesis of intermediate H-6, the feed ratio of intermediate G-6 to intermediate E-5 is 1:1.

[0223] The synthesis of compound 281 is similar to that of compound 1, except that intermediate G-1 is replaced by intermediate H-6. Compound 281 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the M peak was 24 nm, obtained by measuring the fluorescence spectrometer of the Horiba Fluorolog-3 series.

[0224]

[0225] The synthesis of intermediate H-7 is similar to that of intermediate G-1, except that intermediate G-6 replaces raw material F-1, and intermediate E-6 replaces intermediate E-1. In the synthesis of intermediate H-7, the feed ratio of intermediate G-6 and intermediate E-6 is 1:1.

[0226] The synthesis of compound 282 is similar to that of compound 1, except that intermediate G-1 is replaced by intermediate H-7. Compound 282 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the M peak was 24 nm, obtained by measuring the fluorescence spectrometer of the Horiba Fluorolog-3 series.

[0227]

[0228] The synthesis of intermediate G-8 is similar to that of intermediate G-1, except that raw material F-2 replaces raw material F-1, and intermediate E-2 replaces intermediate E-1. In the synthesis of intermediate G-8, the feed ratio of raw material F-2 and intermediate E-2 is 1:1.

[0229] The synthesis of intermediate H-8 is similar to that of intermediate G-1, except that intermediate G-8 replaces raw material F-1, and intermediate E-5 replaces intermediate E-1. In the synthesis of intermediate H-8, the feed ratio of intermediate G-8 to intermediate E-5 is 1:1.

[0230] The synthesis of compound 339 is similar to that of compound 1, except that intermediate G-1 is replaced by intermediate H-8. Compound 339 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the peak (M) was 25 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0231] The structural characterization of the compounds obtained in each embodiment is shown in Table 1.

[0232] Table 1

[0233]

[0234]

[0235] The following describes in detail the application effects of the organic electroluminescent materials synthesized in this invention in devices through device examples 1-8 and device comparative examples 1-2. The fabrication processes of device examples 2-8 and device comparative examples 1-2 are completely identical to those of device example 1, and the same substrate and electrode materials are used, with the electrode film thickness remaining consistent. The only difference is the replacement of the light-emitting layer material in the device. The layer structures and test results of each device example are shown in Tables 2-1 and 3, respectively.

[0236] Device Example 1

[0237] like Figure 1 As shown, the transparent substrate layer 1 is transparent glass. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), washed with pure water, dried, and then subjected to ultraviolet-ozone washing to remove organic residues on the transparent ITO surface. After the above washing, HT-1 and HI-1 with a thickness of 10nm are deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 120nm thick layer of HT-1 is deposited as a hole transport layer 4. Subsequently, a 100nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the organic electroluminescent device is fabricated, using RH-1 as the host material and compound 1 as the dopant material, with a mass ratio of RH-1 to compound 1 of 98:2, and a film thickness of 40nm. Following the aforementioned light-emitting layer 6, ET-1 and Liq are vacuum-deposited at a mass ratio of 1:1, with a film thickness of 35 nm. This layer serves as the electron transport layer 7. On the electron transport layer 7, a 1 nm thick LiF layer is fabricated using a vacuum evaporation apparatus. This layer serves as the electron injection layer 8. On the electron injection layer 8, an 80 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9. This layer serves as the cathode layer 9.

[0238] The application effects of the organic electroluminescent materials synthesized in this invention in devices are described in detail below through device examples 9-16 and device comparative examples 3-4. The fabrication processes of device examples 10-16 and device comparative examples 3-4 are completely identical to those of device example 9, and the same substrate and electrode materials are used, with the electrode film thickness remaining consistent. The only difference is the replacement of the light-emitting layer material in the device. The layer structures and test results of each device example are shown in Tables 2-1 and 3, respectively.

[0239] Device Example 9

[0240] The transparent substrate layer 1 is transparent glass. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, a 10nm thick layer of HT-1 and HI-1 is deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 120nm thick layer of HT-1 is deposited as a hole transport layer 4. Finally, a 100nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking material is deposited, the light-emitting layer 6 of the organic electroluminescent device is fabricated. RH-1 is used as the host material, and RD-1 and Compound 1 are used as dopants. RD-1 is the first dopant, and Compound 1 is the second dopant. The mass ratio of RH-1, RD-1, and Compound 1 is 90.5:8:1.5, and the thickness of the light-emitting layer is 40 nm. Following the light-emitting layer 6, ET-1 and Liq are vacuum-deposited at a mass ratio of 1:1, resulting in a thickness of 35 nm. This layer is the electron transport layer 7. On the electron transport layer 7, a 1 nm thick LiF layer is fabricated using a vacuum evaporation apparatus. This layer is the electron injection layer 8. On the electron injection layer 8, an 80 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9. This layer serves as the cathode layer 9.

[0241] The molecular structural formulas of the relevant materials are shown below:

[0242]

[0243] After completing the organic electroluminescent device as described above, the anode and cathode are connected using a known driving circuit, and the current efficiency, peak emission, and lifetime of the device are measured. Examples and comparative examples of devices prepared using the same method are shown in Table 2-2; the test results for the current efficiency and lifetime of the obtained devices are shown in Table 3.

[0244] Table 2-1

[0245]

[0246]

[0247] Table 2-2

[0248]

[0249]

[0250] Table 3

[0251]

[0252] Note: Current efficiency and luminous peak value were measured using an IVL (current-voltage-luminance) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.), at 10 mA / cm². 2 The following test was conducted; the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc. of Japan. LT95 refers to the time it takes for the device's brightness to decay to 95%, at 50mA / cm. 2 Next test;

[0253] As can be seen from the device data results in Table 3, compared with the comparative compounds ref-1 and ref-2, the compound of the present invention can achieve the effect of red light emission very well and has higher current efficiency; compared with the devices of Comparative Examples 1-4, the current efficiency and lifetime of the device are significantly improved compared with organic electroluminescent devices of known materials.

[0254] In summary, the above are merely preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A boron-containing resonance-type organic compound, characterized in that: The structure of the boron-containing resonance organic compound is shown in general formula (1): In general formula (1), R1 represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or C1 to C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups; The occurrence of M1, M2, M3, M5, and M6 being the same or different each time indicates that C6 to C6 are substituted or not substituted by one or more R values. 30 aryl group, C2-C2 substituted or unsubstituted by one or more R groups. 30 One of the heteroaryl groups; Ar1 represents C1 to C1, whether substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C3-C, substituted or unsubstituted 30 Silyl groups, substituted or unsubstituted C2-C3 groups 30 Boronyl groups, substituted or unsubstituted C2-C3 groups 30 Thioalkyl groups, C6-C6 substituted or unsubstituted with one or more R groups. 30 aryl group, C2-C2 with or without one or more R-substituted or unsubstituted groups. 30 One of the heteroaryl groups; The presence of R, whether the same or different, indicates a deuterium atom, a halogen atom, a cyano group, or C1-C1 atoms that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups; Ar1 and M3 are not connected or are connected through connect; Y1, Y2, Y3, Y4, Y5, Y6, Y7, and Y8 are each independently represented as C1 to C8 cells with or without substituents. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C3-C, substituted or unsubstituted 30 Silyl groups, substituted or unsubstituted C2-C3 groups 30 Boronyl groups, substituted or unsubstituted C2-C3 groups 30 Thioalkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Y1 and Y2, Y3 and Y4, Y5 and Y6, Y7 and Y8 are either not connected to each other or are connected to form C6 to C6 by one or more Rs, either substituted or unsubstituted. 30 aryl group, C2-C2 with or without one or more R-substituted or unsubstituted groups. 30 Heteroaryl groups, C3-C substituted or unsubstituted with one or more R groups. 10 cycloalkyl; X is represented as O, S, N-R0; R0 represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a C1-C group that is substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 heteroaryl, C2-C 10 alkenyl, C2-C 10 Alkyne group, C1-C 10 Alkoxy, C6~C 10 Any one or more of the aryloxy groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

2. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The structure of the boron-containing resonance-type organic compound is shown in general formula (1-1): In general formula (1-1), the definitions of X, R1, M1, M2, M3, M5, M6, Y1, Y2, Y3, Y4, Y5, Y6, Y7, and Y8 are the same as those in general formula (1) of claim 1; M4 represents C6-C6 substituted or unsubstituted with one or more R groups. 30 aryl group, C2-C2 with or without one or more R-substituted or unsubstituted groups. 30 One of the heteroaryl groups; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 heteroaryl, C2-C 10 alkenyl, C2-C 10 Alkyne group, C1-C 10 Alkoxy, C6~C 10 Any one or more of the aryloxy groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

3. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The structure of the boron-containing resonance organic compound is shown in any one of general formulas (2-1) to (2-2): In general formulas (2-1) to (2-2), the definitions of M5, M6, Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, R1, X, and Ar1 are the same as those in general formula (1) of claim 1; Each occurrence of Z independently is represented as N, C-(H), or C-(R). a ); The R a Represented as deuterium atom, halogen atom, cyano group, C1-C with or without substituents. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 heteroaryl, C2-C 10 alkenyl, C2-C 10 Alkyne group, C1-C 10 Alkoxy, C6~C 10 Any one or more of aryloxy and arylamino groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

4. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The structure of the boron-containing resonance organic compound is shown in any one of general formulas (3-1) to (3-10): In general formulas (3-1) to (3-10), the definitions of Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, R1, X, and Ar1 are the same as those in general formula (1) of claim 1; Each occurrence of Z independently is represented as N, C-(H), or C-(R). a ); The R a Represented as deuterium atom, halogen atom, cyano group, C1-C with or without substituents. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 heteroaryl, C2-C 10 alkenyl, C2-C 10 Alkyne group, C1-C 10 Alkoxy, C6~C 10 Any one or more of aryloxy and arylamino groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

5. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The structure of the boron-containing resonance organic compound is shown in any one of general formulas (4-1) to (4-13): In general formulas (4-1) to (4-13), the definitions of R1 and X are the same as those in general formula (1) of claim 1; Each occurrence of Z independently is represented as N, C-(H), or C-(R). a ); The R a Represented as deuterium atom, halogen atom, cyano group, C1-C with or without substituents. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl or fluorine-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 heteroaryl, C2-C 10 alkenyl, C2-C 10 Alkyne group, C1-C 10 Alkoxy, C6~C 10 Any one or more of aryloxy and arylamino groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

6. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The structure of the boron-containing resonance organic compound is shown in any one of general formulas (5-1) to (5-11): In general formulas (5-1) to (5-11), the definition of R1 is the same as that in general formula (1) of claim 1; Each occurrence of Z independently is represented as N, C-(H), or C-(R). a ); The R a Represented as deuterium atom, halogen atom, cyano group, C1-C with or without substituents. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups; R2 and R3 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, and C1-C1 atoms substituted or unsubstituted, respectively. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, C6-C6 substituted or unsubstituted groups 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 heteroaryl, C2-C 10 alkenyl, C2-C 10 Alkyne group, C1-C 10 Alkoxy, C6~C 10 Any one or more of aryloxy and arylamino groups; The heteroatom of the heteroaryl group is selected from one or more of O, S, N, Si, and B.

7. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The structure of the boron-containing resonance organic compound is shown in any one of general formulas (6-1) to (6-3): In general formulas (6-1) to (6-3), the definitions of Y3, Y4, Y5, Y6, R1, X, and Ar1 are the same as those in general formula (1) of claim 1; Each occurrence of Z independently is represented as N, C-(H), or C-(R). a ); The R a Represented as deuterium atom, halogen atom, cyano group, C1-C with or without substituents. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups; R'1, R'2, R'3, R'4, R'5, R'6, R'7, R'8, and R'9 are respectively independently represented as a deuterium atom, a halogen atom, a cyano group, and C1-C1 atoms substituted or unsubstituted with substituents. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, C1-C6 groups substituted or unsubstituted 10 Alkoxy groups, substituted or unsubstituted C6-C6 groups 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 heteroaryl, C2-C substituted or unsubstituted 30 Boronyl groups, C3-C6 groups substituted or unsubstituted 30 One of the silane groups; m3, m4, m5, m6, m7, and m8 are each independently represented as 0, 1, 2, 3, or 4; m1, m2, and m9 can be independently represented as 0, 1, 2, or 3; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1-C1 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, fluorine-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Aryl, C2~C 30 heteroaryl and deuterium-substituted C2-C 30 heteroaryl, C2-C 10 alkenyl, C2-C 10 Alkyne group, C1-C 10 Alkoxy, C6~C 10 Any one or more of aryloxy and arylamino groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

8. The boron-containing organic compound according to any one of claims 1-7, characterized in that, R1 represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group (substituted or unsubstituted), a methyl group (substituted or unsubstituted), an ethyl group (substituted or unsubstituted), an isopropyl group (substituted or unsubstituted), a tert-butyl group (substituted or unsubstituted), a tert-pentyl group (substituted or unsubstituted), a cyclopentyl group (substituted or unsubstituted), a cyclohexyl group (substituted or unsubstituted), a phenyl group (substituted or unsubstituted), or a group with a substituted group. Diphenyl groups with or without substituted substituents, triphenyl groups with or without substituted substituents, diphenyl ether groups with or without substituted substituents, naphthyl groups with or without substituted substituents, anthracene groups with or without substituted substituents, phenanthryl groups with or without substituted substituents, pyridyl groups with or without substituted substituents, quinolinyl groups with or without substituted substituents, furanyl groups with or without substituted substituents, thiophenyl groups with or without substituted substituents, and benzene groups with or without substituted substituents. benzofuranyl, dibenzofuranyl (substituted or unsubstituted), dibenzothiophenyl (substituted or unsubstituted), benzodibenzofuranyl (substituted or unsubstituted), benzodibenzothiophenyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), diphenylfluorenyl (substituted or unsubstituted), and others. Or one of the following: spirofluorenyl or unsubstituted, xanthone or substituted, triazine or substituted, methoxy or substituted, tert-butoxy or substituted, diphenylamino or substituted, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl or substituted, indole or substituted, or benzoindole or substituted. M1, M2, M3, M4, M5, and M6 represent a phenyl group substituted or unsubstituted with one or more Rs, a diphenyl group substituted or unsubstituted with one or more Rs, a terphenyl group substituted or unsubstituted with one or more Rs, a naphthyl group substituted or unsubstituted with one or more Rs, an anthraquinyl group substituted or unsubstituted with one or more Rs, a phenanthryl group substituted or unsubstituted with one or more Rs, a pyridyl group substituted or unsubstituted with one or more Rs, a quinolinyl group substituted or unsubstituted with one or more Rs, a furanyl group substituted or unsubstituted with one or more Rs, a thiophenyl group substituted or unsubstituted with one or more Rs, a benzofuranyl group substituted or unsubstituted with one or more Rs, or a group substituted or unsubstituted with one or more Rs. One of the following: substituted dibenzofuranyl, dibenzothiophenylyl (substituted or unsubstituted with one or more Rs), carbazoyl (substituted or unsubstituted with one or more Rs), N-phenylcarbazoyl (substituted or unsubstituted with one or more Rs), 9,9-dimethylfluorenyl (substituted or unsubstituted with one or more Rs), spirofluorenyl (substituted or unsubstituted with one or more Rs), xanthoneyl (substituted or unsubstituted with one or more Rs), triazineyl (substituted or unsubstituted with one or more Rs), 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl (substituted or unsubstituted with one or more Rs), indoleyl (substituted or unsubstituted with one or more Rs), and benzoindoleyl (substituted or unsubstituted with one or more Rs). The R, R a R'1, R'2, R'3, R'4, R'5, R'6, R'7, R'8, and R'9 are independently represented as a deuterium atom, a halogen atom, a cyano group, an adamantyl group (substituted or unsubstituted), a methyl group (substituted or unsubstituted), an ethyl group (substituted or unsubstituted), an isopropyl group (substituted or unsubstituted), a tert-butyl group (substituted or unsubstituted), a tert-pentyl group (substituted or unsubstituted), a cyclopentyl group (substituted or unsubstituted), and a group substituted or... Unsubstituted cyclohexyl, phenyl groups substituted or unsubstituted, diphenyl groups substituted or unsubstituted, terphenyl groups substituted or unsubstituted, diphenyl ether groups substituted or unsubstituted, naphthyl groups substituted or unsubstituted, anthraquinyl groups substituted or unsubstituted, phenanthryl groups substituted or unsubstituted, pyridyl groups substituted or unsubstituted, quinolinyl groups substituted or unsubstituted, furanyl groups substituted or unsubstituted, and other substituents. Thiophene group, benzofuran group (substituted or unsubstituted), dibenzofuran group (substituted or unsubstituted), dibenzothiophene group (substituted or unsubstituted), benzodibenzofuran group (substituted or unsubstituted), benzodibenzothiophene group (substituted or unsubstituted), carbazolyl group (substituted or unsubstituted), N-phenylcarbazolyl group (substituted or unsubstituted), 9,9-dimethylfluorenyl group (substituted or unsubstituted), diphenylfluorene group (substituted or unsubstituted) One of the following: spirofluorenyl (substituted or unsubstituted), xanthone (substituted or unsubstituted), triazine (substituted or unsubstituted), methoxy (substituted or unsubstituted), tert-butoxy (substituted or unsubstituted), diphenylamino (substituted or unsubstituted), 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl (substituted or unsubstituted), indolyl (substituted or unsubstituted), and benzoindolyl (substituted or unsubstituted). R0, R2, and R3 are independently represented as hydrogen atom, deuterium atom, halogen atom, cyano group, adamantyl group (substituted or unsubstituted), methyl group (substituted or unsubstituted), ethyl group (substituted or unsubstituted), isopropyl group (substituted or unsubstituted), tert-butyl group (substituted or unsubstituted), tert-pentyl group (substituted or unsubstituted), cyclopentyl group (substituted or unsubstituted), cyclohexyl group (substituted or unsubstituted), and [other groups are not specified in the original text]. Phenyl, diphenyl (substituted or unsubstituted), triphenyl (substituted or unsubstituted), diphenyl ether (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraquinyl (substituted or unsubstituted), phenanthryl (substituted or unsubstituted), pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), and so on. Unsubstituted benzofuranyl, dibenzofuranyl (substituted or unsubstituted), dibenzothiophenyl (substituted or unsubstituted), benzodibenzofuranyl (substituted or unsubstituted), benzodibenzothiophenyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), diphenylfluorenyl (substituted or unsubstituted), and so on. One of the following: substituted or unsubstituted spirofluorenyl, substituted or unsubstituted xanthone, substituted or unsubstituted triazine, substituted or unsubstituted methoxy, substituted or unsubstituted tert-butoxy, substituted or unsubstituted diphenylamino, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted indole, and substituted or unsubstituted benzoindole. Y1, Y2, Y3, Y4, Y5, Y6, Y7, Y8, and Ar1 represent: adamantyl (substituted or unsubstituted), methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), tert-pentyl (substituted or unsubstituted), cyclopentyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), and [other compounds, substituted or unsubstituted]. Phenyl, diphenyl (substituted or unsubstituted), triphenyl (substituted or unsubstituted), diphenyl ether (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraquinyl (substituted or unsubstituted), phenanthryl (substituted or unsubstituted), pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), and so on. Substituted benzofuranyl, dibenzofuranyl (substituted or unsubstituted), dibenzothiophenyl (substituted or unsubstituted), benzodibenzofuranyl (substituted or unsubstituted), benzodibenzothiophenyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), diphenylfluorenyl (substituted or unsubstituted), and so on. One of the following: substituted or unsubstituted spirofluorenyl, substituted or unsubstituted xanthone, substituted or unsubstituted triazine, substituted or unsubstituted methoxy, substituted or unsubstituted tert-butoxy, substituted or unsubstituted diphenylamino, substituted or unsubstituted 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, substituted or unsubstituted indole, and substituted or unsubstituted benzoindole. The substituents used for the substituent groups are selected from deuterium, chlorine, fluorine, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, phenyl, diphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiophene, indoleyl, pyrroleyl, and dibenzofuranyl. Dibenzothiophene, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, azirphenanthrenel, diphenylamino, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, benzoindolyl, deuterated adamantyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated tert-amyl, deuterated tert-butyl, deuterated... Butyl, deuterated phenyl, deuterated diphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated pyridazinyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated quinoxalinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated furanyl, deuterated thiopheneyl, deuterated indole One or more of the following: dolomyl, deuterated pyrroleyl, deuterated dibenzofuranyl, deuterated dibenzothiopheneyl, deuterated 9,9-dimethylfluorenyl, deuterated spirofluorenyl, deuterated carbazolyl, deuterated N-phenylcarbazolyl, deuterated carbazolinyl, deuterated azirophenonel, deuterated 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and deuterated benzoindolyl.

9. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The specific structural formula of the boron-containing resonance-type organic compound is any one of the following structures:

10. An organic light-emitting device, comprising a substrate, a first electrode, an organic functional material layer, and a second electrode, wherein the first electrode is located on the substrate, the organic functional material layer is located on the first electrode, and the second electrode is located on the organic functional material layer, characterized in that: The organic functional material layer contains the boron-containing resonant organic compound as described in any one of claims 1-9; Preferably, the organic functional material layer includes a light-emitting layer, and the light-emitting layer contains the boron-containing resonant organic compound according to any one of claims 1-9; Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the dopant material is a boron-containing resonant organic compound as described in any one of claims 1-9.

11. The organic light-emitting device according to claim 10, wherein the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material, characterized in that: The exciton sensitizing material is a complex containing a metal element, and the doping material is a boron-containing resonant organic compound as described in any one of claims 1-9.

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