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 organic compounds and the organic electroluminescent device comprising it, belong to semiconductor technical field, the present application provides the structure of compound as shown in general formula (1): The 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 existing technology, this invention provides a boron-containing resonant organic compound and an organic electroluminescent device prepared therefrom. The boron-containing resonant organic 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), X1, X2, X3, and X4 are independently represented as B atoms or N atoms;

[0009] R1-R 14 Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane;

[0010] M1 and M2 are independently represented as one or more R-substituted or unsubstituted C6-C6 groups. 30 The aromatic ring, one or more R-substituted or unsubstituted C2-C 30 One of the aromatic rings;

[0011] Ar represents C1 to C2, whether substituted or unsubstituted. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane;

[0012] Z is represented as CH or C-R0;

[0013] Each occurrence of R0 is independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C1 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane;

[0014] Each occurrence of R, whether the same or different, represents a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane;

[0015] R1 and Ar are not connected or are connected by a single bond, double bond, -O-, -S-, -N(Ra)-, -B(Ra)-, -C(RbRc)-, -Si(RdRe)- or -C(Rp)=C(Rq)-;

[0016] The R1-R 14 Any two adjacent groups are not connected or are connected by a single bond, double bond, -O-, -S-, -N(Ra)-, -B(Ra)-, -C(RbRc)-, -Si(RdRe)- or -C(Rp)=C(Rq)-;

[0017] Ra, Rb, Rc, Rd, Re, Rp, and Rq are each independently represented as a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0018] Rb and Rc are not connected or are connected in a ring by a single bond, double bond, -O- or -S-;

[0019] The Rd and Re are not connected or are connected in a loop by a single bond, double bond, -O- or -S-;

[0020] The substituents used to replace the aforementioned substituted groups are optionally 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 10alkenyl, C2-C 10 Alkyne group, C1-C 10 Alkoxy, C6~C 10 Any one or more of aryloxy and arylamino groups;

[0021] The heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B.

[0022] Furthermore, the structure of the boron-containing resonance organic compound is shown in general formula (2):

[0023]

[0024] In general formula (2), Z, M1, M2, X1, X2, X3, X4, R2-R 14 The definition is the same as the limitation in general formula (1);

[0025] X5 is represented as -N(Ra)- or -B(Ra)-;

[0026] Ra represents a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0027] M3 represents C6-C6 with or without one or more R-substituted or unsubstituted C6-C6. 30 The aromatic ring, one or more R-substituted or unsubstituted C2-C 30 One of the aromatic rings;

[0028] Each occurrence of R, whether the same or different, represents a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane;

[0029] The substituents used to replace the aforementioned substituted groups are optionally 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;

[0030] The heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B.

[0031] Preferably, in general formula (2), X1 and X3 represent B atoms; X2 and X4 represent N atoms; and X5 represents -N(Ra)-.

[0032] Preferably, the structure of the boron-containing resonance organic compound is as shown in general formula (2-1):

[0033]

[0034] In general formula (2-1), Z, M1, M2, M3, R a R2-R 14 The definition is the same as the limitation in general formula (2).

[0035] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (3) to (4):

[0036]

[0037] In general formulas (3) and (4), Z, M1, M2, X1, X2, X3, X4, R2-R 14 The definition is the same as the limitation in general formula (2);

[0038] In general formula (3), X5 represents a B atom or a N atom;

[0039] In general formula (4), X5 is represented as -N(Ra)- or -B(Ra)-;

[0040] Ra represents a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0041] Y1 is represented as -O-, -S-, -N(R'a)-, -C(R'bR'c)- or -Si(R'dR'e)-;

[0042] R'a, R'b, R'c, R'd, and R'e are each independently represented as a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0043] R 15 -R 27 Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane;

[0044] The substituents used to replace the aforementioned substituted groups are optionally 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;

[0045] The heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B;

[0046] Preferably, in general formula (3), X1 and X3 represent B atoms; X2, X4, and X5 represent N atoms;

[0047] Preferably, in general formula (4), X1 and X3 represent B atoms; X2 and X4 represent N atoms; and X5 represents -N(Ra)-.

[0048] Preferably, the structure of the boron-containing resonance organic compound is as shown in general formula (3-1) or general formula (4-1):

[0049]

[0050] In general formula (3-1), Z, M1, M2, R a R2-R 27 The definition is the same as the limitation in general formula (3);

[0051] In general formula (4-1), Z, M1, M2, R a Y1, R2-R 18 The definition is the same as the limitation in general formula (4).

[0052] Furthermore, the structure of the boron-containing resonance organic compound is shown in general formulas (5) to (9):

[0053]

[0054]

[0055] In general formulas (5) to (9), Z, X1, X2, X3, X4, R2-R 14 The definition is the same as the limitation in general formula (2);

[0056] In general formulas (6) to (9), X5 represents a B atom or a N atom;

[0057] In general formula (5), X5 is represented as -N(Ra)- or -B(Ra)-;

[0058] Ra represents a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0059] Y1, Y2, Y3, and Y4 are independently represented as -O-, -S-, -N(R'a)-, -C(R'bR'c)-, or -Si(R'dR'e)-;

[0060] R'a, R'b, R'c, R'd, and R'e are each independently represented as a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0061] R 15 -R 39 Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane;

[0062] The substituents used to replace the aforementioned substituted groups are optionally 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;

[0063] The heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B;

[0064] Preferably, in general formulas (6) to (9), X1 and X3 represent B atoms; X2, X4, and X5 represent N atoms;

[0065] Preferably, in general formula (5), X1 and X3 represent B atoms; X2 and X4 represent N atoms; and X5 represents -N(Ra)-.

[0066] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (10) to (14):

[0067]

[0068] In general formulas (10) to (14), Z, R2-R 14 The definition is the same as the limitation in general formula (2);

[0069] Ra represents a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C1-C 10Alkoxy, substituted or unsubstituted C6-C 30 aryloxy group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0070] Y1, Y2, Y3, and Y4 are independently represented as -O-, -S-, -N(R'a)-, -C(R'bR'c)-, or -Si(R'dR'e)-;

[0071] R'a, R'b, R'c, R'd, and R'e are each independently represented as a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0072] R 15 -R 39 Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane;

[0073] The substituents used to replace the aforementioned substituted groups are optionally 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~C30 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;

[0074] The heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B;

[0075] Furthermore, the R1-R 39 R0, Ra, Rb, Rc, Rd, Re, Rp, and Rq 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, diphenyl, deuterated diphenyl, tritium 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. The following is a list of 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.

[0076] The R, Ra, Rb, Rc, Rd, Re, Rp, Rq, R'a, R'b, R'c, R'd, and R'e are independently represented as deuterium atom, halogen atom, cyano, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, and methyl-substituted cyclopentyl. Cyclohexyl, phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, tritium 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-dimethyl The following is a list of fluorenyl, spirofluorenyl, 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 boroalkyl, methoxy, tert-butoxy, and diphenylamino.

[0077] The Ar group is independently represented as 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, tritium biphenyl, 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 The following are substituted phenyl groups: methyl-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, tert-butoxy, and diphenylamino.

[0078] M1, M2, and M3 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, tert-butyl-substituted phenyl, methyl-substituted... One of the following: 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.

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

[0080] Furthermore, the M1 and M2 rings are represented by the following groups:

[0081] Any one of them;

[0082] Each of the M3 rings can be independently represented by the following ring structures:

[0083]

[0084] Any one of them;

[0085] Each occurrence of Z being the same or different is represented as C-R0;

[0086] The R1-R 39 R0, Ra, Rb, Rc, Rd, Re, Rp, and Rq are each independently represented by the following structures: hydrogen atom, cyano group, deuterium atom, methyl group, ethyl group, isopropyl group, tert-butyl group, etc. Any one of them;

[0087] The R, Ra, Rb, Rc, Rd, Re, Rp, Rq, R'a, R'b, R'c, R'd, and R'e are independently represented as cyano, deuterium, methyl, ethyl, isopropyl, tert-butyl, and so on.

[0088]

[0089] Any one of them;

[0090] The Ar is represented by the following structure:

[0091]

[0092] Any one of them.

[0093] Furthermore, the specific structural formula of the boron-containing resonance organic compound is any one of the following structures:

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108] The present invention also provides an organic light-emitting device comprising a substrate, a first electrode, a functional layer, and a second electrode, wherein the first electrode is located on the substrate, the functional layer is located on the first electrode, the second electrode is located on the functional layer, and the functional layer contains the boron-containing resonant organic compound of the present invention.

[0109] Preferably, the functional layer includes a light-emitting layer, which comprises a host material and a dopant material, wherein the dopant material is the boron-containing resonant organic compound of the present invention.

[0110] Furthermore, the light-emitting layer comprises a first host material, a second host material, and a dopant material, wherein at least one of the first host material and the second host material is a TADF material, and the dopant material is a boron-containing resonant organic compound as described in this invention.

[0111] 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.

[0112] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0113] (1) The compound of the present invention can be used as a doping material for organic electroluminescent devices, and can emit red fluorescence under the action of an electric field. It can be applied to OLED lighting or OLED display fields.

[0114] (2) The compounds of the present invention have a narrower FWHM spectrum, which can effectively improve the color gamut of the device.

[0115] (3) The compounds of the present invention can achieve higher efficiency in top-emitting devices. Attached Figure Description

[0116] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device using the materials listed in this invention;

[0117] 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

[0118] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0119] 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.

[0120] In this invention, the substituted or unsubstituted aromatic amino group refers to... Wherein Q1 and Q2 represent substituted or unsubstituted aromatic groups, and Q1 and Q2 preferably represent substituted or unsubstituted C6-C groups. 30 Aryl or substituted or unsubstituted C2-C 30 Mixed aromatic compounds.

[0121] In this invention, C6-C is substituted or unsubstituted. 30The aryl group refers to an aryl group with 6 to 30 carbon atoms, preferably an aryl group with 6 to 20 carbon atoms, and even more preferably an aryl group with 6 to 10 carbon atoms. It is preferably a substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrene, substituted or unsubstituted biphenyl, substituted or unsubstituted para-triphenyl, substituted or unsubstituted meta-triphenyl, substituted or unsubstituted... The group may contain, but is not limited to, substituted or unsubstituted triphenyl, substituted or unsubstituted peryl, substituted or unsubstituted indole, and combinations thereof or combinations of the foregoing groups forming a fused ring.

[0122] In this invention, substituted or unsubstituted C2-C 30 Heteroaryl refers to heteroaryl groups with 2 to 30 carbon atoms, preferably heteroaryl groups with 2 to 20 carbon atoms, preferably heteroaryl groups with 4 to 20 carbon atoms, preferably heteroaryl groups with 4 to 10 carbon atoms, preferably heteroaryl groups with 5 to 10 carbon atoms, preferably substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or Unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted naphthinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenthiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted tyloyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiaphenyl, substituted or unsubstituted carbazoyl, combinations thereof, or fused rings of the foregoing groups, but not limited thereto.

[0123] In this invention, substituted or unsubstituted C2-C 30 The number of heteroatoms in the heteroaryl group is 1-5, preferably 1-4, preferably 1-3, preferably 1-2, and preferably 1.

[0124] The C1-C of this invention 10Alkyl (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 5 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and preferably methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, etc., but not limited to these.

[0125] The C3-C of this invention 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, C4-C9 cycloalkyl groups are preferred, C5-C8 cycloalkyl groups are more preferred, and C5-C7 cycloalkyl groups are particularly preferred. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

[0126] The halogen atom mentioned in this invention refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0127] The C1-C of this invention 10 Alkoxy groups include, but are not limited to, alkoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, or isopropoxy.

[0128] The C2-C of this invention 10 Alkenyl refers to vinyl, allyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1,1-dimethylallyl, 1-methylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, and 3-phenyl-1-butenyl, etc., but is not limited to these.

[0129] 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 PI film substrate is preferred. There are no particular limitations on the thickness of the substrate.

[0130] 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.

[0131] 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.

[0132] 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.

[0133] 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.

[0134] 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.

[0135] 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.

[0136] Preferably, the main organic material used as the hole injection layer of the present invention may be selected from the following prior art:

[0137] The compounds disclosed in WO2017191896A1, JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, and CN105439999A, but not limited thereto.

[0138] 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.

[0139] 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.

[0140] 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.

[0141] 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.

[0142] Preferably, the hole transport layer material of the present invention may be selected from the compounds disclosed in the prior art:

[0143]

[0144] 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.

[0145] 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.

[0146] In one embodiment of the present invention, the electron blocking layer material may be selected from the compounds disclosed in the prior art:

[0147]

[0148] The thickness of the electron blocking layer of this invention can be 1-100 nm, but the thickness is not limited to this range.

[0149] 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.

[0150] 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.

[0151] 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.

[0152] 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.

[0153] 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.

[0154] 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:

[0155]

[0156] 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.

[0157] 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.

[0158] 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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] 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.

[0163] Synthesis Examples

[0164] 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;

[0165] Synthesis of Compound 1:

[0166]

[0167] Synthesis of intermediate b-1: Starting material B-1 (4.14 g, 12 mmol) was dissolved in 80 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 3.8 mL of n-butyllithium (1.6 M) n-hexane solution was slowly added. After stirring at -78 °C for 2 hours, 10 mL of tetrahydrofuran solution of starting material A-1 (2.03 g, 12 mmol) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. The reaction mixture was quenched with water, the aqueous layer was separated, filtered under reduced pressure, dried over MgSO4, filtered again, and evaporated by rotary evaporation. The resulting product was then column-purified to obtain intermediate b-1.

[0168] Synthesis of intermediate C-1: Intermediate b-1 (3.48 g, 8 mmol) was dissolved in 50 mL of acetic acid solution, followed by the slow addition of a few drops of HCl solution and stirring at 80 °C. After the reaction was complete, the solution was slowly quenched with an aqueous solution of NaHCO3, and the aqueous layer was separated and extracted with an aqueous solution of dichloromethane. The organic layer was then dried and dried with MgSO4. The resulting compound was subjected to column chromatography and recrystallization to obtain intermediate C-1.

[0169]

[0170] Synthesis of intermediate G-1: In a two-necked flask, starting material E-1 (2.15 g, 8 mmol), starting material F-1 (1.64 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. The mixture was degassed by a vacuum-nitrogen purging cycle, and then heated under reflux for 25 hours. 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 G-1.

[0171]

[0172] Synthesis of intermediate D-1: In a two-necked flask, starting material H-1 (1.52 g, 5 mmol), intermediate C-1 (2.09 g, 5 mmol), CuI catalyst (0.5 mmol, 0.10 g), and K3PO4 (25 mmol, 5.3 g) were added. Then, under a nitrogen atmosphere, trans-1,2-cyclohexanediamine (1.8 mmol, 0.2 g) and 90 mL of dioxane were added. The mixture was stirred at 120 °C for 16 hours. The reaction mixture was then cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compound was separated by silica gel column chromatography to obtain intermediate D-1.

[0173] Synthesis of Intermediate I-1: Intermediate D-1 (1.92 g, 3 mmol), intermediate G-1 (1.18 g, 3 mmol), Pd2(dba)3 (0.25 mmol, 0.23 g), tri-tert-butylphosphine tetrafluoroborate (0.5 mmol, 0.15 g), sodium tert-butoxide (15 mmol, 1.44 g), and toluene (100 mL) were added to a two-necked flask. The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 24 hours. 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 I-1.

[0174] Synthesis of intermediate J-1: Intermediate I-1 (1.91 g, 2 mmol) was dissolved in 25 mL of tetrahydrofuran, and 0.54 g (3 mmol) of NBS was added. The mixture was stirred at room temperature for 24 h under light-protected conditions. After the reaction was complete, the mixture was extracted with water / ethyl acetate, the solvent was removed by rotary evaporation, and then purified by silica gel column chromatography to obtain intermediate J-1. LC-MS: Measured value: 1031.45 ([M+H) + ), Precision quality: 1030.34.

[0175] Synthesis of intermediate L-1: Intermediate J-1 (1.55 g, 1.5 mmol), starting material K-1 (0.56 g, 2 mmol), Pd2(dba)3 (0.15 mmol, 0.14 g), tri-tert-butylphosphine tetrafluoroborate (0.25 mmol, 0.07 g), sodium tert-butoxide (7.5 mmol, 0.72 g), and toluene (60 mL) were added to a two-necked flask. The mixture was degassed by a vacuum-nitrogen purging cycle and then heated under reflux for 20 hours. 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 L-1.

[0176] Synthesis of Compound 1: In a sealed pressure-resistant tube under nitrogen protection, intermediate L-1 (1.23 g, 1 mmol) and 25 mL of anhydrous o-dichlorobenzene were added. After cooling to -78 °C, 4.8 mL of 2.5 M tert-butyllithium-n-hexane solution was added dropwise. The mixture was transferred to 60 °C and reacted for 3 hours. The reaction was then cooled to -40 °C, and 1 mL (10 mmol) of boron tribromide was added dropwise. After slowly restoring to room temperature, the reaction was allowed to continue for 3 hours. At 0 °C, 1.8 mL (10 mmol) of ultra-dry N,N-diisopropylethylamine was added dropwise. The reaction mixture was heated to 180 °C and reacted for 12 hours. After cooling to room temperature, the low-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, filtered, dried over anhydrous sodium sulfate, and the filtrate was collected. The filtrate was concentrated and purified by column chromatography to obtain Compound 1. Elemental analysis and structure (C 83 H 87 Theoretical values ​​for B2N3S: C, 84.46; H, 7.43; N, 3.56; S, 2.72; Measured values: C, 84.36; H, 7.41; N, 3.76; S, 2.52. LC-MS: Measured value: 1180.89 ([M+H]) + ), exact mass: 1179.68. Compound 1 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.

[0177] Synthesis of compound 152:

[0178]

[0179] Synthesis of intermediate A-2: Starting material H-1 (1.52 g, 5 mmol), intermediate C-1 (4.18 g, 10 mmol), CuI catalyst (1 mmol, 0.19 g), and K3PO4 (40 mmol, 8.49 g) were added to a two-necked flask. Then, under a nitrogen atmosphere, trans-1,2-cyclohexanediamine (3.6 mmol, 0.41 g) and 150 mL of dioxane were added. The mixture was stirred at 120 °C for 19 hours. The reaction mixture was then cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compound was separated by silica gel column chromatography to obtain intermediate A-2.

[0180] The synthesis of intermediate B-2 is similar to that of intermediate J-1, except that intermediate I-1 is replaced by intermediate A-2.

[0181] The synthesis of intermediate C-2 is similar to that of intermediate L-1, except that intermediate J-1 is replaced by intermediate B-2.

[0182] The synthesis of compound 152 is similar to that of compound 1, except that intermediate L-1 is replaced by intermediate C-2. Elemental analysis of the structure (C...) 88 H 83 B2N3) Theoretical values: C, 87.77; H, 6.95; N, 3.49; Measured values: C, 87.68; H, 6.89; N, 3.39. LC-MS: Measured value: 1204.78 ([M+H]) + Compound 152 in toluene solution (1 × 10⁻⁶), exact mass 1203.68:. -5 The half-width of the peak (M) was 25 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0183] Synthesis of compound 167:

[0184]

[0185] The synthesis of intermediate G-3 is similar to that of intermediate b-1, except that raw material B-1 is replaced by raw material F-3.

[0186] The synthesis of intermediate H-3 is similar to that of intermediate C-1, except that intermediate b-1 is replaced by intermediate G-3.

[0187]

[0188]

[0189] The synthesis of intermediate B-3 is similar to that of intermediate A-2, except that intermediate C-1 is replaced by intermediate H-3.

[0190] The synthesis of intermediate C-3 is similar to that of intermediate J-1, except that intermediate I-1 is replaced by intermediate B-3.

[0191] The synthesis of intermediate D-3 is similar to that of intermediate L-1, except that intermediate J-1 is replaced by intermediate C-3.

[0192] The synthesis of compound 167 is similar to that of compound 1, except that intermediate L-1 is replaced by intermediate D-3. Elemental analysis and structure (C 72 H 51 B2N3) Theoretical values: C, 88.26; H, 5.25; N, 4.29; Measured values: C, 88.33; H, 5.41; N, 4.33. LC-MS: Measured value: 980.39 ([M+H]) + ), exact mass: 979.43. Compound 167 in toluene solution (1×10⁻⁶) - 5The half-width of the M peak was 24 nm, obtained by measuring the fluorescence spectrometer of the Horiba Fluorolog-3 series.

[0193] Synthesis of compound 223:

[0194]

[0195] Synthesis of intermediate b-4: In a two-necked flask, raw material A-4 (2.15 g, 8 mmol), tripotassium phosphate (1.06 g, 5 mmol), and copper acetylacetonate (65.5 mg, 0.25 mmol) were added. Under nitrogen protection, 60 mL of anhydrous DMF was added, followed by 40 mL of ammonia water (10 mmol). The reaction mixture was stirred at 90 °C for 48 hours, cooled to room temperature, filtered, washed with water, dried, and passed through a column to obtain intermediate b-4.

[0196]

[0197] The synthesis of intermediate C-4 is similar to that of intermediate G-1, except that raw material E-1 is replaced by raw material A-4, and raw material F-1 is replaced by intermediate b-4.

[0198] The synthesis of intermediate D-4 is similar to that of intermediate L-1, except that intermediate J-1 is replaced by intermediate C-3 and raw material K-1 is replaced by intermediate C-4.

[0199] The synthesis of compound 223 is similar to that of compound 1, except that intermediate L-1 is replaced by intermediate D-4. Elemental analysis and structure (C 76 H 51 Theoretical values ​​for B2N3S2: C, 83.59; H, 4.71; N, 3.85; S, 5.87; Measured values: C, 83.76; H, 4.73; N, 3.83; S, 5.81. LC-MS: Measured value: 1092.45 ([M+H]) + ), exact mass: 1091.37. Compound 223 in toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) was 26 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0200] Synthesis of compound 316:

[0201]

[0202] The synthesis of intermediate B-5 is similar to that of intermediate L-1, except that intermediate J-1 is replaced by intermediate C-3 and raw material K-1 is replaced by raw material A-5.

[0203] The synthesis of compound 316 is similar to that of compound 1, except that intermediate L-1 is replaced by intermediate B-5. Elemental analysis of the structure (C...) 72 H 39 Theoretical values ​​for B2N3: C, 89.36; H, 4.06; B, 2.23; N, 4.34; Measured values: C, 89.26; H, 4.16; B, 2.11; N, 4.25. LC-MS: Measured value: 968.23 ([M+H]) + ), exact mass: 967.33. Compound 316 in toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) was 27 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0204] Synthesis of compound 270:

[0205]

[0206] The synthesis of intermediate C-6 is similar to that of intermediate G-1, except that raw material E-1 is replaced by raw material A-6 and raw material F-1 is replaced by raw material B-6.

[0207] The synthesis of intermediate D-6 is similar to that of intermediate L-1, except that intermediate J-1 is replaced by intermediate C-3 and raw material K-1 is replaced by intermediate C-6.

[0208] The synthesis of compound 270 is based on that of compound 1, except that intermediate L-1 is replaced by intermediate D-6. Elemental analysis of the structure (C...) 74 H 51 Theoretical values ​​for B2N3S: C, 85.80; H, 4.96; B, 2.09; N, 4.06; S, 3.09; Measured values: C, 85.82; H, 4.91; B, 2.06; N, 4.03; S, 3.08. LC-MS: Measured value: 1036.43 ([M+H]) + ), exact mass: 1035.40. Compound 270 in toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) was 26 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0209] The following describes in detail the application effects of the organic electroluminescent materials synthesized in this invention in devices through device examples 1-6 and device comparative examples 1-2. The fabrication processes of device examples 2-6 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.

[0210] Device Example 1

[0211] like Figure 1 As shown, the transparent substrate layer 1 is a transparent PI film. 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. 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 OLED light-emitting 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.

[0212] The application effects of the OLED material synthesized in this invention in devices are described in detail below through device examples 7-12 and device comparative examples 3-4. The fabrication processes of device examples 8-12 and device comparative examples 3-4 are completely identical to those of device example 7, and the same substrate material and electrode material 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 2-2 and 3, respectively.

[0213] Device Example 7

[0214] The transparent substrate layer 1 is a transparent PI film. 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. 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 OLED light-emitting device is fabricated, using RH-1 as the host material, compound 1 as the dopant, RD-1 as the first dopant, and compound 1 as the second dopant, with a mass ratio of RH-1, RD-1, and compound 1 of 90.5:8:1.5. The light-emitting layer film thickness is 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.

[0215] The molecular structural formulas of the relevant materials are shown below:

[0216]

[0217] Among them, ref-1 and ref-2 are comparative structures.

[0218] After the organic electroluminescent device is completed as described above, the anode and cathode are connected using a known driving circuit, and the current efficiency and lifetime of the device are measured. Examples and comparisons of devices prepared using the same method are shown in Tables 2-1 and 2-2; the test results of the current efficiency and lifetime of the obtained devices are shown in Table 3.

[0219] Table 2-1

[0220]

[0221] Table 2-2

[0222]

[0223]

[0224] Table 3

[0225]

[0226] 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;

[0227] As can be seen from the device data results in Table 3, compared with the comparative compounds ref-1 and ref-2, it can achieve the effect of red light emission very well and has higher current efficiency; compared with the devices in Comparative Examples 1-4, the current efficiency and lifetime of the device are significantly improved compared with organic electroluminescent devices of known materials.

[0228] 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), X1, X2, X3, and X4 are independently represented as B atoms or N atoms; R1-R 14 Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; M1 and M2 are independently represented as one or more R-substituted or unsubstituted C6-C6 groups. 30 The aromatic ring, one or more R-substituted or unsubstituted C2-C 30 One of the aromatic rings; Ar represents C1 to C2, whether substituted or unsubstituted. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; Z is represented as CH or C-R0; Each occurrence of R0 is independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C1 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; Each occurrence of R, whether the same or different, represents a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; R1 and Ar are not connected or are connected by a single bond, double bond, -O-, -S-, -N(Ra)-, -B(Ra)-, -C(RbRc)-, -Si(RdRe)- or -C(Rp)=C(Rq)-; The R1-R 14 Any two adjacent groups are not connected or are connected by a single bond, double bond, -O-, -S-, -N(Ra)-, -B(Ra)-, -C(RbRc)-, -Si(RdRe)- or -C(Rp)=C(Rq)-; Ra, Rb, Rc, Rd, Re, Rp, and Rq are each independently represented as a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Rb and Rc are not connected or are connected in a ring by a single bond, double bond, -O- or -S-; The Rd and Re are not connected or are connected in a loop by a single bond, double bond, -O- or -S-; The substituents used to replace the aforementioned substituted groups are optionally 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 heteroaryl group and the heteroatom in the heteroaryl ring are 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 organic compound is shown in general formula (2): In general formula (2), Z, M1, M2, X1, X2, X3, X4, R2-R 14 The definition is the same as the limitation in general formula (1); X5 is represented as -N(Ra)- or -B(Ra)-; Ra represents a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; M3 represents C6-C6 with or without one or more R-substituted or unsubstituted C6-C6. 30 The aromatic ring, one or more R-substituted or unsubstituted C2-C 30 One of the aromatic rings; Each occurrence of R, whether the same or different, represents a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; The substituents used to replace the aforementioned substituted groups are optionally 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 heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B; Preferably, in general formula (2), X1 and X3 represent B atoms; X2 and X4 represent N atoms; and X5 represents -N(Ra)-.

3. The boron-containing resonance-type organic compound according to claim 2, characterized in that: The structure of the boron-containing resonance organic compound is shown in any one of general formulas (3) to (4): In general formulas (3) and (4), Z, M1, M2, X1, X2, X3, X4, R2-R 14 The definition is the same as the limitation in general formula (2); In general formula (3), X5 represents a B atom or a N atom; In general formula (4), X5 is represented as -N(Ra)- or -B(Ra)-; Ra represents a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Y1 is represented as -O-, -S-, -N(R'a)-, -C(R'bR'c)- or -Si(R'dR'e)-; R'a, R'b, R'c, R'd, and R'e are each independently represented as a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; R 15 -R 27 Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; The substituents used to replace the aforementioned substituted groups are optionally 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 heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B; Preferably, in general formula (3), X1 and X3 represent B atoms; X2, X4, and X5 represent N atoms; Preferably, in general formula (4), X1 and X3 represent B atoms; X2 and X4 represent N atoms; and X5 represents -N(Ra)-.

4. The boron-containing resonance-type organic compound according to claim 2, characterized in that: The structures of the boron-containing resonance organic compounds are shown in general formulas (5) to (9): In general formulas (5) to (9), Z, X1, X2, X3, X4, R2-R 14 The definition is the same as the limitation in general formula (2); In general formulas (6) to (9), X5 represents a B atom or a N atom; In general formula (5), X5 is represented as -N(Ra)- or -B(Ra)-; Ra represents a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C1 group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Y1, Y2, Y3, and Y4 are independently represented as -O-, -S-, -N(R'a)-, -C(R'bR'c)-, or -Si(R'dR'e)-; R'a, R'b, R'c, R'd, and R'e are each independently represented as a deuterium atom, a halogen atom, a cyano group, or a substituted or unsubstituted C1-C group. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 aryloxy group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; R 15 -R 39 Each can be represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C2-C 10 Alkenyl, substituted or unsubstituted C2-C 10 Alkyne group, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of heteroaryl, substituted or unsubstituted borane, or substituted or unsubstituted silane; The substituents used to replace the aforementioned substituted groups are optionally 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 heteroaryl group and the heteroatom in the heteroaryl ring are selected from one or more of O, S, N, Si, and B; Preferably, in general formulas (6) to (9), X1 and X3 represent B atoms; X2, X4, and X5 represent N atoms; Preferably, in general formula (5), X1 and X3 represent B atoms; X2 and X4 represent N atoms; and X5 represents -N(Ra)-.

5. The boron-containing resonance-type organic compound according to any one of claims 1-4, characterized in that, The R1-R 39 R0, Ra, Rb, Rc, Rd, Re, Rp, and Rq 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, diphenyl, deuterated diphenyl, tritium 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. The following is a list of 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. The R, Ra, Rb, Rc, Rd, Re, Rp, Rq, R'a, R'b, R'c, R'd, and R'e are independently represented as deuterium atom, halogen atom, cyano, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, and methyl-substituted cyclopentyl. Cyclohexyl, phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, tritium 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-dimethyl The following is a list of fluorenyl, spirofluorenyl, 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 boronyl, methoxy, tert-butoxy, and diphenylamino. The Ar group is independently represented as 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, tritium biphenyl, 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 The following are substituted phenyl groups: methyl-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, tert-butoxy, and diphenylamino. M1, M2, and M3 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, tert-butyl-substituted phenyl, methyl-substituted... One of the following: 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. The substituents used for the substituent groups are selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheninyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, azirphenanthreneyl, and diphenylamino.

6. The boron-containing resonance-type organic compound according to any one of claims 1-4, characterized in that, The M1 and M2 rings are represented by the following groups: any one of them; Each of the M3 rings can be independently represented by the following ring structures: any one of them; Each occurrence of Z being the same or different is represented as C-R0; The R1-R 39 R0, Ra, Rb, Rc, Rd, Re, Rp, and Rq are each independently represented by the following structures: hydrogen atom, cyano group, deuterium atom, methyl group, ethyl group, isopropyl group, tert-butyl group, etc. Any one of them; The R, Ra, Rb, Rc, Rd, Re, Rp, Rq, R'a, R'b, R'c, R'd, and R'e are independently represented as cyano, deuterium, methyl, ethyl, isopropyl, tert-butyl, and so on. Any one of them; The Ar is represented by the following structure: Any one of them.

7. 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:

8. An organic light-emitting device, comprising a substrate, a first electrode, a functional layer, and a second electrode, wherein the first electrode is located on the substrate, the functional layer is located on the first electrode, and the second electrode is located on the functional layer, characterized in that: The functional layer contains the boron-containing resonance organic compound as described in any one of claims 1-7; Preferably, the functional layer includes a light-emitting layer, which 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 1-7.

9. The organic light-emitting device according to claim 8, wherein the light-emitting layer comprises a first host material, a second host material, and a dopant material, characterized in that: At least one of the first host material and the second host material is a TADF material, and the doping material is a boron-containing resonant organic compound as described in any one of claims 1-7.

10. The organic light-emitting device according to claim 8, 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 resonance organic compound as described in any one of claims 1-7.

Images