Boron-containing resonance type organic compound and organic electroluminescent device containing same

Abstract

The invention relates to a boron-containing resonance type organic compound and an organic electroluminescent device containing the same, and belongs to the technical field of semiconductors, and the structure of the compound provided by the invention is shown as a general formula (1). The material can be used as a luminescent layer green light doping material of an organic electroluminescent device, so that the service life of the device is prolonged.

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 transition (TTF) technology. This technology has lower efficiency but higher color purity, and it has basically met the BT.2020 display specifications. Green and red light use phosphorescence technology, which has high efficiency. Red light is close to the BT.2020 display specifications, while green light is limited by the wider emission spectrum of phosphorescence, which is significantly different from the requirements of high-definition display specifications. In addition, green phosphorescence naturally has a high shoulder peak, making it relatively difficult to improve the color gamut display under traditional device structures. Therefore, developing a new generation of high color purity green organic electroluminescent materials is crucial.

[0003] Since 2020, green light materials with narrow half-width at half-maximum (WHM < 30nm) based on boron-nitrogen resonant structures have been reported successively. Furthermore, several papers on green boron-nitrogen narrow-emission materials and device effects were reported in 2022 and 2023, such as: DOI: 10.1002 / anie.202301930, DOI: 10.1038 / s41566-022-01106-8, DOI: 10.1002 / anie.202313254, DOI: 10.1038 / s41566-022-01083-y, DOI: 10.1002 / anie.202202380, etc., demonstrating the high color purity and efficiency of these materials, which have great potential as a new generation of green organic electroluminescent display materials. However, there are still many technical challenges in the development of green ultra-high color purity materials with boron-nitrogen structures. Existing materials also have the drawbacks of insufficient efficiency and lifespan to meet the needs of mass production. Developing narrow half-peak width green light materials based on boron-nitrogen resonant structures that can meet practical applications is a key technology for the next generation of display devices with high color purity, high color gamut coverage, high efficiency and high immersion.

[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-peak widths (HWHM). Therefore, developing sensitization technologies based on narrow HWHM boron-based 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, when used as a doping material for the light-emitting layer of an organic electroluminescent device, can emit green light.

[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), Z is independently represented as C-(H) or C-(R0); R0 represents a deuterium atom, a halogen atom, a cyano group, or a C1-C1 group substituted or unsubstituted with a substituent. 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted);

[0009] R1 and R2 appearing the same or different each time represent hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, and 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted);

[0010] R1 and R2 are either not connected or connected in a C6-C configuration with or without substituents. 30 Aromatic rings, 5-30 membered heteroaromatic rings substituted or unsubstituted, C5-C6 substituted or unsubstituted 30 Aliphatic rings;

[0011] M1 represents C6 to C6, which are substituted or unsubstituted by one or more R groups. 30 The aromatic ring, or a 5-30 membered heteroaromatic ring substituted or unsubstituted with one or more Rs;

[0012] Each occurrence of R, whether the same or different, represents 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted);

[0013] The replacement of R is either a single bond or a parallel ring connection;

[0014] Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 appearing the same or different each time indicates that C1 to C6 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 unsubstituted10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, one of 5-30 membered heteroaryl groups substituted or unsubstituted, one of borane groups substituted or unsubstituted, and one of silane groups substituted or unsubstituted;

[0015] Ar3 and Ar4 are either not connected or connected in a C6-C configuration with or without substituents. 30 Aromatic rings, 5-30 membered heteroaromatic rings substituted or unsubstituted, C5-C6 substituted or unsubstituted 30 Aliphatic rings;

[0016] Ar5 and Ar6 are either not connected or connected in a C6-C6 configuration with or without substituents. 30 Aromatic rings, 5-30 membered heteroaromatic rings substituted or unsubstituted, C5-C6 substituted or unsubstituted 30 Aliphatic rings;

[0017] Ar2 is either not connected to M1 or connected in a C6-C configuration with or without substituents. 30 Aromatic rings, 5-30 membered heteroaromatic rings substituted or unsubstituted, C5-C6 substituted or unsubstituted 30 Aliphatic rings;

[0018] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl;

[0019] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0020] Furthermore, in general formula (1), the number of Zs represented as C-(R0) on the same benzene ring is 1, 2 or 3.

[0021] Furthermore, R1 and R2 are not connected or are connected in a ring by single bonds, double bonds, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)- or -C(R'6)=C(R'7)-;

[0022] Furthermore, Ar3 and Ar4 are not connected or are connected in a ring by single bonds, double bonds, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)- or -C(R'6)=C(R'7)-;

[0023] Furthermore, Ar5 and Ar6 are not connected or are connected in a ring by single bonds, double bonds, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)- or -C(R'6)=C(R'7)-;

[0024] Furthermore, Ar2 and M1 are not connected or are connected in a ring by single bonds, double bonds, -O-, -S-, -N(R'1)-, -C(R'2R'3)-, -Si(R'4R'5)- or -C(R'6)=C(R'7)-;

[0025] R'1, R'2, R'3, R'4, R'5, R'6, and R'7 are each independently represented as C1 to C2 groups that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl groups, 5-30 membered heteroaryl groups substituted or unsubstituted;

[0026] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, and C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 Cycloalkyl and deuterium-substituted 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 Any one or more of the heteroaryl groups;

[0027] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0028] Furthermore, the structure of the boron-containing resonance organic compound is shown in general formula (A-1):

[0029]

[0030] In general formula (A-1), the definitions of R1, R2, Ar2, Ar3, Ar4, Ar5, Ar6, M1, and Z are the same as those in general formula (1).

[0031] Furthermore, in general formula (A-1), the number of Zs represented as C-(R0) on the same benzene ring is 1, 2, or 3.

[0032] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (B-1) to (B-8):

[0033]

[0034]

[0035] In general formulas (B-1) to (B-8), the definitions of R1, R2, Ar1, Ar3, Ar4, Ar5, Ar6, and Z are the same as those in general formula (1);

[0036] X1 is represented as O, S, N-(R) d ) or C(R e (R) f );

[0037] R d Represented as C6-C6 with or without substituents. 30 One of aryl, substituted or unsubstituted 5-30 heteroaryl groups;

[0038] R e R f Represented as C1-C1 with or without substituents. 10 Alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl groups, 5-30 membered heteroaryl groups substituted or unsubstituted;

[0039] Ar7 and Ar8 are each represented independently as C1-C1 cells with or without substituents, 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, one of 5-30 membered heteroaryl groups substituted or unsubstituted, one of borane alkyl groups substituted or unsubstituted, and one of silane alkyl groups substituted or unsubstituted;

[0040] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl;

[0041] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0042] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (C-1) to (C-3):

[0043]

[0044] In general formulas (C-1) to (C-3), the definitions of R1, R2, Ar1, Ar2, M1, and Z are the same as those in general formula (1).

[0045] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (D-1) to (D-8):

[0046]

[0047]

[0048] In general formulas (D-1) to (D-8), the definitions of R1, R2, and Z are the same as those in general formula (1);

[0049] X1 is represented as O, S, N-(R) d ) or C(R e (R) f );

[0050] R d Represented as C6-C6 with or without substituents. 30 One of aryl, substituted or unsubstituted 5-30 heteroaryl groups;

[0051] R e R f Represented as C1-C1 with or without substituents. 10 Alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl groups, 5-30 membered heteroaryl groups substituted or unsubstituted;

[0052] Ar7 and Ar8 are each represented independently as C1-C1 cells with or without substituents, respectively. 10 Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, one of 5-30 membered heteroaryl groups substituted or unsubstituted, one of borane alkyl groups substituted or unsubstituted, and one of silane alkyl groups substituted or unsubstituted;

[0053] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl;

[0054] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0055] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (E-1) to (E-12):

[0056]

[0057]

[0058] In general formulas (E-1) to (E-12), the definitions of R1, R2, Ar1, and Ar2 are the same as those in general formula (1);

[0059] X1 is represented as O, S, N-(R) d ) or C(R e (R) f );

[0060] R d Represented as C6-C6 with or without substituents. 30 One of aryl, substituted or unsubstituted 5-30 heteroaryl groups;

[0061] R e R f Represented as C1-C1 with or without substituents. 10 Alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl groups, 5-30 membered heteroaryl groups substituted or unsubstituted;

[0062] Ar7 and Ar8 are each represented independently as C1-C1 cells with or without substituents, respectively. 10Alkyl groups, substituted or unsubstituted C3-C6 groups 10 Cycloalkyl, C2-C6 substituted or unsubstituted 10 Alkenyl, C2-C, substituted or unsubstituted 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, one of 5-30 membered heteroaryl groups substituted or unsubstituted, one of borane alkyl groups substituted or unsubstituted, and one of silane alkyl groups substituted or unsubstituted;

[0063] R3, R4, R5, R6, R7, R8, R9, R 10 Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, one of 5-30 membered heteroaryl groups substituted or unsubstituted, one of borane alkyl groups substituted or unsubstituted, and one of silane alkyl groups substituted or unsubstituted;

[0064] m, n, s, k, v represent 0, 1, 2, 3, or 4;

[0065] p, q, j, g represent 0, 1, 2, or 3;

[0066] h represents 0, 1, 2, 3, 4 or 5;

[0067] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl;

[0068] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0069] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (F-1) to (F-8):

[0070]

[0071] In general formulas (F-1) to (F-8), the definitions of R1, R2, and Z are the same as those in general formula (1);

[0072] X1 is represented as O, S, N-(R) d ) or C(R e (R) f );

[0073] R d Represented as C6-C6 with or without substituents. 30 One of aryl, substituted or unsubstituted 5-30 heteroaryl groups;

[0074] R e R f Represented as C1-C1 with or without substituents. 10 Alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl groups, 5-30 membered heteroaryl groups substituted or unsubstituted;

[0075] Ar7 and Ar8 are each represented independently as C1-C1 cells with or without substituents, 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, one of 5-30 membered heteroaryl groups substituted or unsubstituted, one of borane alkyl groups substituted or unsubstituted, and one of silane alkyl groups substituted or unsubstituted;

[0076] R3, R4, R5, R6, R7, and R8 appearing in the same or different forms each time represent hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, and 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, one of 5-30 membered heteroaryl groups substituted or unsubstituted, one of borane alkyl groups substituted or unsubstituted, and one of silane alkyl groups substituted or unsubstituted;

[0077] The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl;

[0078] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0079] Further, M1 represents any one of the following groups that are substituted or unsubstituted by R: phenyl, naphthyl, anthraceneyl, phenanthryl, pyridyl, quinolinyl, furanyl, thiopheneyl, benzofuranyl, benzothiopheneyl, dibenzofuranyl, dibenzothiopheneyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, indole[3,2,1-jk]carbazoyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and spirofluorenyl;

[0080] The R0 and R represent a deuterium atom, a halogen atom, a cyano group, 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 cyclohexyl group (substituted or unsubstituted), an adamantyl group (substituted or unsubstituted), a phenyl group (substituted or unsubstituted), a diphenyl group (substituted or unsubstituted), a terphenyl group (substituted or unsubstituted), a naphthyl group (substituted or unsubstituted), anthracene group (substituted or unsubstituted), a phenanthryl group (substituted or unsubstituted), a pyridyl group (substituted or unsubstituted), and a group (substituted or unsubstituted). Quinolinyl, furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), benzothiopheneyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiopheneyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), 9,9-diphenylfluorenyl (substituted or unsubstituted), spirofluorenyl (substituted or unsubstituted), amino (substituted or unsubstituted), triazineyl (substituted or unsubstituted).

[0081] The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10Each of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, methyl group (substituted or unsubstituted), ethyl group (substituted or unsubstituted), isopropyl group (substituted or unsubstituted), tert-butyl group (substituted or unsubstituted), cyclohexyl group (substituted or unsubstituted), adamantyl group (substituted or unsubstituted), phenyl group (substituted or unsubstituted), diphenyl group (substituted or unsubstituted), terphenyl group (substituted or unsubstituted), naphthyl group (substituted or unsubstituted), anthracene group (substituted or unsubstituted), phenanthryl group (substituted or unsubstituted), pyridyl group (substituted or unsubstituted), and [other groups, substituted or unsubstituted]. Quinolinyl, furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), benzothiopheneyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiopheneyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), 9,9-diphenylfluorenyl (substituted or unsubstituted), spirofluorenyl (substituted or unsubstituted), amino (substituted or unsubstituted), triazineyl (substituted or unsubstituted).

[0082] Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are independently represented as methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), adamantyl (substituted or unsubstituted), phenyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraceneyl (substituted or unsubstituted), phenanthryl (substituted or unsubstituted), pyridyl (substituted or unsubstituted), and so on. Substituent-substituted or unsubstituted quinolinyl, substituent-substituted or unsubstituted furanyl, substituent-substituted or unsubstituted thiopheneyl, substituent-substituted or unsubstituted benzofuranyl, substituent-substituted or unsubstituted benzothiopheneyl, substituent-substituted or unsubstituted dibenzofuranyl, substituent-substituted or unsubstituted dibenzothiopheneyl, substituent-substituted or unsubstituted carbazoyl, substituent-substituted or unsubstituted N-phenylcarbazoyl, substituent-substituted or unsubstituted 9,9-dimethylfluorenyl, substituent-substituted or unsubstituted 9,9-diphenylfluorenyl, substituent-substituted or unsubstituted spirofluorenyl, substituent-substituted or unsubstituted amino, substituent-substituted or unsubstituted triazineyl;

[0083] The R dRepresented as phenyl with or without substituents, diphenyl with or without substituents, terphenyl with or without substituents, naphthyl with or without substituents, anthraceneyl with or without substituents, phenanthryl with or without substituents, pyridyl with or without substituents, quinolinyl with or without substituents, furanyl with or without substituents, thiopheneyl with or without substituents, benzofuranyl with or without substituents, etc. Substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted N-phenylcarbazolyl group, substituted or unsubstituted 9,9-dimethylfluorenyl group, substituted or unsubstituted 9,9-diphenylfluorenyl group, substituted or unsubstituted spirofluorenyl group, substituted or unsubstituted amino group, substituted or unsubstituted triazine group;

[0084] The R e R f Represented as methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), adamantyl (substituted or unsubstituted), phenyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraceneyl (substituted or unsubstituted), phenanthrene (substituted or unsubstituted), pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), and others. Substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl;

[0085] R'1, R'2, R'3, R'4, R'5, R'6, and R'7 are independently represented as methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), adamantyl (substituted or unsubstituted), phenyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraceneyl (substituted or unsubstituted), phenanthryl (substituted or unsubstituted), pyridyl (substituted or unsubstituted), and so on. Quinolinyl group (substituted or unsubstituted), furanyl group (substituted or unsubstituted), thiophene group (substituted or unsubstituted), benzofuranyl group (substituted or unsubstituted), benzothiophene group (substituted or unsubstituted), dibenzofuranyl group (substituted or unsubstituted), dibenzothiophene group (substituted or unsubstituted), carbazoyl group (substituted or unsubstituted), N-phenylcarbazoyl group (substituted or unsubstituted), 9,9-dimethylfluorenyl group (substituted or unsubstituted), 9,9-diphenylfluorenyl group (substituted or unsubstituted), spirofluorenyl group (substituted or unsubstituted), amino group (substituted or unsubstituted), triazine group (substituted or unsubstituted).

[0086] The substituents are selected from one or more of the following: deuterium, chlorine, fluorine, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

[0087] Furthermore, M1 can be represented as any of the following ring structures:

[0088]

[0089] X2 is represented as O, S, N-(R) d ) or C(R e (R) f );

[0090] R d Represented as phenyl;

[0091] R e R f It is indicated as methyl or phenyl;

[0092] Each occurrence of Y independently is represented as N, CH, or C-(R) c );

[0093] The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 Each can be represented independently as shown in the following structure:

[0094] Hydrogen atom, deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano, trifluoromethyl

[0095]

[0096] any one of them;

[0097] The R0, R, R c Each can be represented independently as shown in the following structure:

[0098] Deuterium atom, methyl, ethyl, isopropyl, tert-butyl, cyano, trifluoromethyl,

[0099]

[0100] any one of them;

[0101] Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are represented by the following structure:

[0102] Methyl, isopropyl, tert-butyl,

[0103]

[0104] Furthermore, the specific structural formula of the boron-containing resonance organic compound is any one of the following structures:

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122] The present invention also provides an organic light-emitting device, comprising a substrate, a first electrode, a second electrode, and a functional layer in sequence, wherein the functional layer is located between the first electrode and the second electrode, and the functional layer contains the boron-containing resonant organic compound described above in the present invention.

[0123] 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 described above in this invention.

[0124] Preferably, the functional layer includes a light-emitting layer, which includes a first host material, a second host material, and a dopant material. 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 above in this invention.

[0125] Furthermore, the functional layer includes a light-emitting layer, which 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 above in this invention.

[0126] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0127] (1) The compound of the present invention can be used in organic electroluminescent devices as a doping material for the light-emitting layer. It can emit green fluorescence under the action of an electric field and can be applied in the fields of OLED lighting or OLED display.

[0128] (2) The compounds of this invention have a narrower FWHM spectrum, which can effectively improve the color gamut of the device;

[0129] (3) The compound of the present invention, as a green light doping material, can effectively improve device efficiency and device lifetime;

[0130] The compounds of this invention have a narrow half-width at half-maximum (WHM) characteristic and can be used as green light doping materials for the emitting layer of organic electroluminescent devices, thereby improving the efficiency and lifetime of the devices. Attached Figure Description

[0131] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device using the materials listed in this invention;

[0132] Wherein, 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 a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer. Detailed Implementation

[0133] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0134] 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.

[0135] In this invention, the substituted or unsubstituted aromatic amino group referred to in this invention means... Wherein W1 and W2 represent aromatic groups that are substituted or unsubstituted, and W1 and W2 preferably represent C6-C groups that are substituted or unsubstituted. 30 Aryl groups are 5-30 membered heteroaryl groups, either substituted or unsubstituted.

[0136] In this invention, the silane group that is substituted or unsubstituted refers to... Where W3, W4, and W5 represent C1-C1 segments that are substituted or unsubstituted. 10 Alkyl groups or C3-C6 groups substituted or unsubstituted 10 Cycloalkyl groups, preferably C3-C6 substituted or unsubstituted. 10 Silyl group.

[0137] In this invention, the borane group that is substituted or unsubstituted refers to... Where W6 and W7 represent C1-C cells 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 Heteroaryl groups, preferably C2-C, are substituted or unsubstituted. 10 Boronyl alkyl group.

[0138] W1 and W2 are preferably represented as phenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), anthraquinone (substituted or unsubstituted), phenanthrene (substituted or unsubstituted), dimethylfluorenyl (substituted or unsubstituted), diphenylfluorenyl (substituted or unsubstituted), spirofluorenyl (substituted or unsubstituted), fused tetraphenyl (substituted or unsubstituted), pyrene (substituted or unsubstituted), and other compounds (substituted or unsubstituted). Substituents, triphenylene, perylene, indole, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, furanyl, thiophene, pyrrole, pyrazolyl, imidazolyl, triazolyl, and others. 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 triazine group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted benzofuranyl group. Indolyl, quinolinyl (substituted or unsubstituted), isoquinolinyl (substituted or unsubstituted), quinazolinyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), quinoxalinyl (substituted or unsubstituted), naphthidyl (substituted or unsubstituted), benzoxazinyl (substituted or unsubstituted), benzothiazinyl (substituted or unsubstituted), benzopyrimidinyl (substituted or unsubstituted), acridineyl (substituted or unsubstituted), phenazinyl (substituted or unsubstituted) The following are examples of substituted or unsubstituted phenoxazinyl, 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, but not limited to these.

[0139] W3, W4, and W5 are preferably represented as methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), propyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), butyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), isobutyl (substituted or unsubstituted), 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), and [other compounds, substituted or unsubstituted]. 2-Methylpentyl, 3-methylpentyl (substituted or unsubstituted), 1-butylpentyl (substituted or unsubstituted), 2-methylbutyl (substituted or unsubstituted), secondary pentyl (substituted or unsubstituted), neohexyl (substituted or unsubstituted), 2-ethylhexyl (substituted or unsubstituted), cyclopropyl (substituted or unsubstituted), cyclobutyl (substituted or unsubstituted), cyclopentyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), 4-methylcyclohexyl (substituted or unsubstituted), 4,4-dimethylcyclohexyl (substituted or unsubstituted), adamantyl (substituted or unsubstituted), cyclooctyl (substituted or unsubstituted), cycloheptyl (substituted or unsubstituted), but not limited thereto.

[0140] W6 and W7 are preferably represented as methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), propyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), butyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), isobutyl (substituted or unsubstituted), sec-butyl (substituted or unsubstituted), neopentyl (substituted or unsubstituted), n-pentyl (substituted or unsubstituted), isopentyl (substituted or unsubstituted), and so on. 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), secondary pentyl (substituted or unsubstituted), neopentyl (substituted or unsubstituted) Hexyl, 2-ethylhexyl (substituted or unsubstituted), cyclopropyl (substituted or unsubstituted), cyclobutyl (substituted or unsubstituted), cyclopentyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), 4-methylcyclohexyl (substituted or unsubstituted), 4,4-dimethylcyclohexyl (substituted or unsubstituted), adamantyl (substituted or unsubstituted), cyclooctyl (substituted or unsubstituted), cycloheptyl (substituted or unsubstituted), and others. Substituted or unsubstituted phenyl, naphthyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), anthraquinone (substituted or unsubstituted), phenanthrene (substituted or unsubstituted), dimethylfluorenyl (substituted or unsubstituted), diphenylfluorenyl (substituted or unsubstituted), spirofluorenyl (substituted or unsubstituted), fused tetraphenyl (substituted or unsubstituted), pyrene (substituted or unsubstituted), and so on. Substituents, triphenylene, perylene, indole, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, furanyl, thiophene, pyrrole, pyrazolyl, imidazolyl, triazolyl, and others. 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 triazine group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted benzofuranyl group. Indolyl, quinolinyl (substituted or unsubstituted), isoquinolinyl (substituted or unsubstituted), quinazolinyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), quinoxalinyl (substituted or unsubstituted), naphthidyl (substituted or unsubstituted), benzoxazinyl (substituted or unsubstituted), benzothiazinyl (substituted or unsubstituted), benzopyrimidinyl (substituted or unsubstituted), acridineyl (substituted or unsubstituted), phenazinyl (substituted or unsubstituted) The following are examples of substituted or unsubstituted phenoxazinyl, 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, but not limited to these.

[0141] In this invention, C6-C is substituted or unsubstituted. 30 Aryl groups refer to phenyl groups (substituted or unsubstituted), naphthyl groups (substituted or unsubstituted), anthraquinyl groups (substituted or unsubstituted), fluorenyl groups (substituted or unsubstituted), dimethylfluorenyl groups (substituted or unsubstituted), diphenylfluorenyl groups (substituted or unsubstituted), spirofluorenyl groups (substituted or unsubstituted), phenanthyl groups (substituted or unsubstituted), fused tetraphenyl groups (substituted or unsubstituted), pyrene groups (substituted or unsubstituted), biphenyl groups (substituted or unsubstituted), para-triphenyl groups (substituted or unsubstituted), meta-triphenyl groups (substituted or unsubstituted), and other substituted or unsubstituted compounds. The group may include, 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 combination thereof, or a fused ring of the aforementioned groups.

[0142] In this invention, C6-C 30 Aryl groups refer to those composed of phenyl, naphthyl, anthraceneyl, fluorenyl, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, phenanthrene, tetraphenyl, pyrene, biphenyl, para-triphenyl, meta-triphenyl, etc. Fused rings of alkyl, triphenylene, perylene, indene, or combinations thereof, but not limited to these groups.

[0143] In this invention, deuterium-substituted C6-C 30 Aryl groups refer to deuterated phenyl groups, deuterated naphthyl groups, deuterated anthracene groups, deuterated fluorenyl groups, deuterated dimethylfluorenyl groups, deuterated diphenylfluorenyl groups, deuterated spirofluorenyl groups, deuterated phenanthrene groups, deuterated tetraphenyl groups, deuterated pyrene groups, deuterated biphenyl groups, deuterated para-triphenyl groups, deuterated meta-triphenyl groups, and deuterated... The group may include, but is not limited to, fused rings of alkyl, deuterated triphenylene, deuterated peryl, deuterated indene, combinations thereof, or combinations of the foregoing groups.

[0144] In this invention, the 5-30 membered heteroaryl groups, whether substituted or unsubstituted, refer to furanyl, thiophene, pyrrole, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyrimidinyl, pyrimidinyl, pyrazinyl, triazine, triazine, benzofuranyl, benzothiophene, and others. The following are fused rings, including but not limited to: substituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted naphthidyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted benziazinyl, substituted or unsubstituted benziazinyl, substituted or unsubstituted benziazinyl, substituted or unsubstituted benziazinyl, substituted or unsubstituted fumonyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl, combinations thereof, or combinations of the foregoing groups.

[0145] In this invention, 5-30 member heteroaryl refers to furanyl, thiophene, pyrrole, pyrazolyl, imidazole, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, benzothiophene, benzoimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinolinyl, naphridinyl, benzooxazinyl, benzothiazinyl, acridineyl, benazinoyl, benazinoylthiazinyl, benazinoyloxazinyl, fumonyl, dibenzofuranyl, dibenzothiophene, carbazoleyl, or combinations thereof or combinations of the aforementioned groups forming a fused ring, but is not limited thereto.

[0146] In this invention, deuterated 5-30-membered heteroaryl groups refer to 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 triazine, deuterated benzofuranyl, deuterated benzothiophene, and deuterated benzimidazolyl. The following are fused rings, including but not limited to: deuterated indolyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated quinazolinyl, deuterated quinolinyl, deuterated naphridyl, deuterated benzoxazinyl, deuterated benzothiazinyl, deuterated acridineyl, deuterated benzazinyl, deuterated benzthiazinyl, deuterated benzoxazinyl, deuterated fumonyl, deuterated dibenzofuranyl, deuterated dibenzothiophenyl, deuterated carbazoyl, combinations thereof, or combinations of the foregoing groups.

[0147] The C1-C substituted or unsubstituted C1-C of the present invention 10 Alkyl groups (including straight-chain alkyl and branched-chain alkyl) refer to, but are not limited to, methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), propyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), butyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), isobutyl (substituted or unsubstituted), sec-butyl (substituted or unsubstituted), neopentyl (substituted or unsubstituted), n-pentyl (substituted or unsubstituted), isopentyl (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), etc.

[0148] The C1-C of this invention 10 Alkyl groups (including straight-chain alkyl and branched-chain alkyl) refer to 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 are not limited to these.

[0149] The deuterium-substituted C1-C of the present invention 10Alkyl groups (including straight-chain alkyl groups and branched-chain alkyl groups) refer to, but are not limited to, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, deuterated tert-butyl, deuterated isobutyl, deuterated sec-butyl, deuterated neopentyl, deuterated n-pentyl, deuterated isopentyl, deuterated octyl, deuterated heptyl, deuterated n-decyl, deuterated 1-methylpentyl, deuterated 2-methylpentyl, deuterated 3-methylpentyl, and deuterated 1-butylpentyl.

[0150] The C3-C of this invention, whether substituted or unsubstituted, 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, whether substituted or unsubstituted, are preferred; C5-C8 cycloalkyl groups, whether substituted or unsubstituted, are more preferred; and C5-C7 cycloalkyl groups, whether substituted or unsubstituted, 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, etc., whether substituted or unsubstituted.

[0151] 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.

[0152] The deuterium-substituted C3-C of the present invention 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, deuterated C4-C9 cycloalkyl groups are preferred, more preferably deuterated C5-C8 cycloalkyl groups, and particularly preferably deuterated C5-C7 cycloalkyl groups. Non-limiting examples may include, but are not limited to, deuterated cyclopropyl, deuterated cyclobutyl, deuterated cyclopentyl, deuterated cyclohexyl, deuterated 4-methylcyclohexyl, deuterated 4,4-dimethylcyclohexyl, deuterated adamantyl, and deuterated cycloheptyl.

[0153] The halogen atom mentioned in this invention refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0154] The C1-C of this invention10 Alkoxy groups include, but are not limited to, alkoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, or isopropoxy.

[0155] 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.

[0156] The substituents may be selected from one or more of the following: deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthryl, pyridinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheninyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthryl.

[0157] 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.

[0158] 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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] 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.

[0163] 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.

[0164] Preferably, the main organic material used as the hole injection layer of the present invention may be selected from the following compounds disclosed in the prior art: JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, CN105439999A or CN103108859A.

[0165] 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.

[0166] 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.

[0167] 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.

[0168] 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.

[0169] Preferably, the hole transport layer material of the present invention may be selected from the compounds disclosed in the prior art:

[0170]

[0171] 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.

[0172] The thickness of the hole transport layer of the present invention can be 5-200 nm, preferably 10-150 nm, and more preferably 20-100 nm, but the thickness is not limited to this range.

[0173] In one embodiment of the present invention, the electron blocking layer material may be selected from the compounds disclosed in the prior art:

[0174]

[0175] The thickness of the electron blocking layer of the present invention can be 1-50 nm, preferably 5-40 nm, but the thickness is not limited to this range.

[0176] 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.

[0177] The light-emitting layer may include a host material and a dopant material. The host material may be a green 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.

[0178] The light-emitting layer can contain a single-substrate material or a dual-substrate material;

[0179] The dual-body material comprises a first body material and a second body material, wherein preferably at least one of the first body material and the second body material is a TADF material;

[0180] TADF materials refer to materials with thermally activated delayed fluorescence properties. They are characterized by a small energy difference between the first excited singlet and triplet states, allowing for the simultaneous utilization of both singlet and triplet excitons generated within the device, thus enabling the exciton utilization rate of electrogenerated excitons within the device to approach 100%. Compared to traditional fluorescent materials, TADF materials exhibit higher exciton utilization.

[0181] The light-emitting layer may include a host material, an exciton-sensitizing material, and a dopant material;

[0182] Exciton-sensitized materials refer to materials that enable the luminescent material in the luminescent layer to fully utilize electroexcitons, thereby allowing the luminescent layer to ultimately produce the emission spectrum of the sensitized material. Exciton sensitizers may perform functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The boron-containing resonance organic compound shown in the general formula (1) of this invention, when used in combination with the exciton-sensitized material, has a significant improvement effect on problems such as device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0183] 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 97:3-87:13, based on mass.

[0184] 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.

[0185] In this invention, the electron transport region may include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed on the light-emitting layer, but is not limited thereto.

[0186] A hole-blocking layer is a layer that prevents holes injected from the anode from penetrating the light-emitting layer and entering the cathode, thereby extending the device's lifetime and improving its performance. The hole-blocking layer of this invention can be disposed on top of the light-emitting layer. As the hole-blocking layer material for the organic electroluminescent device of this invention, compounds with hole-blocking properties known in the prior art can be used, for example:

[0187]

[0188] The thickness of the hole blocking layer of the present invention can be 2-200nm, preferably 5-150nm, more preferably 5-50nm, but the thickness is not limited to this range.

[0189] An electron transport layer may be disposed above the light-emitting layer or (if present) a hole-blocking layer. The electron transport layer material is one that readily receives electrons from the cathode and transfers these received 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:

[0190]

[0191] 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.

[0192] 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.

[0193] 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.

[0194] 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.

[0195] 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, BaF, 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, LiF / Ca, LiF / Al, Mo, Ti, or compounds or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0196] 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.

[0197] 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, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, onto a substrate. In this regard, 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.

[0198] Preparation of compounds

[0199] 1. Synthesis of intermediate P

[0200] Synthesis of intermediate P1:

[0201]

[0202] Add raw material T1 (25 mmol, 4.5 g), potassium carbonate (62.5 mmol, 8.6 g), tricyclohexylphosphine (1.25 mmol, 0.35 g), and palladium acetate (0.4 mmol, 90 mg) to a two-necked flask. Add 100 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add raw material R1 (25 mmol, 6.7 g) under nitrogen protection and stir at 140 °C for 12 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate P1.

[0203] Synthesis of intermediate P2:

[0204]

[0205] Add raw material T2 (25 mmol, 7.3 g), potassium carbonate (62.5 mmol, 8.6 g), tricyclohexylphosphine (1.25 mmol, 0.35 g), and palladium acetate (0.4 mmol, 90 mg) to a two-necked flask. Add 100 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add raw material R1 (25 mmol, 6.7 g) under nitrogen protection and stir at 140 °C for 13 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate P2.

[0206] Synthesis of intermediate P3:

[0207]

[0208] Add raw material T3 (25 mmol, 10.1 g), potassium carbonate (62.5 mmol, 8.6 g), tricyclohexylphosphine (1.25 mmol, 0.35 g), and palladium acetate (0.4 mmol, 90 mg) to a two-necked flask. Add 100 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add raw material R1 (25 mmol, 6.7 g) under nitrogen protection and stir at 140 °C for 15 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate P3.

[0209] Synthesis of intermediate P4:

[0210]

[0211] Add raw material T1 (25 mmol, 4.5 g), potassium carbonate (62.5 mmol, 8.6 g), tricyclohexylphosphine (1.25 mmol, 0.35 g), and palladium acetate (0.4 mmol, 90 mg) to a two-necked flask. Add 100 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add raw material R2 (25 mmol, 6.7 g) under nitrogen protection and stir at 140 °C for 12 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate P4.

[0212] Synthesis of intermediate P5:

[0213]

[0214] Add raw material T2 (25 mmol, 7.3 g), potassium carbonate (62.5 mmol, 8.6 g), tricyclohexylphosphine (1.25 mmol, 0.35 g), and palladium acetate (0.4 mmol, 90 mg) to a two-necked flask. Add 100 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add raw material R2 (25 mmol, 6.7 g) under nitrogen protection and stir at 140 °C for 13 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate P5.

[0215] Synthesis of intermediate P6:

[0216]

[0217] Add raw material T4 (18.4 mmol, 4.3 g) and cesium carbonate (55.2 mmol, 18.0 g) to a two-necked flask. Add 120 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add raw material R3 (20.2 mmol, 4.2 g) under nitrogen protection. Reflux the solution under magnetic stirring for 24 hours. Cool, filter, wash with water, dry, and purify by column chromatography to obtain intermediate X1.

[0218] Intermediate X1 (10.0 mmol, 4.2 g), tetra-n-butylammonium bromide (nBu4NBr) (1.0 mmol, 0.3 g), triphenylphosphine (0.5 mmol, 0.13 g), palladium acetate catalyst (0.2 mmol, 0.05 g), potassium carbonate (20.0 mmol, 2.8 g), and DMAc (50 mL) were added sequentially to a sealed pressure-resistant tube. The mixture was then heated under reflux and stirred for 48 hours under nitrogen protection. After cooling, the organic phase was separated and collected. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. The compound was then separated by silica gel column chromatography to obtain intermediate P6.

[0219] Synthesis of intermediate P7:

[0220]

[0221] Add raw material R4 (10 mmol, 4.4 g) and 50 mL of anhydrous DMF sequentially to a three-necked flask. Under nitrogen protection, add NaH (12 mmol, 0.4 g) coated with mineral oil (65%) in portions under ice-water bath conditions. Stir the mixture for 0.5 hours, then slowly add a solution of 4-methoxybenzyl chloride (10 mmol, 1.6 g) dissolved in 10 mL of anhydrous DMF. After the reaction is complete, quench the reaction with 120 mL of water and filter out the large amount of precipitate. Collect the precipitate, dry it with dichloromethane solution and anhydrous sodium sulfate, filter it, concentrate the reaction solution, and purify it by silica gel column chromatography to obtain intermediate X2.

[0222] Under nitrogen protection, intermediate X2 (4.79 mmol, 2.7 g) and 50 mL of anhydrous diethyl ether were added sequentially to a two-necked flask at -78 °C. Then, a 1.6 M solution of n-butyllithium in n-hexane (10.07 mmol, 6.3 mL) was slowly added in portions. Next, starting material T5 (5.27 mmol, 1.0 g) was added to this solution, and the mixture was stirred at room temperature for 4 hours. After the reaction was complete, the mixture was treated with an aqueous solution of ammonium chloride and then extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The intermediate X3 was purified by silica gel column chromatography.

[0223]

[0224] Intermediate X3 (5 mmol, 2.6 g), a mixed solution of tetrahydrofuran and ethanol (50 mL) were added sequentially to a two-necked flask. Then, Pd(OH)₂ / C (0.2 mmol, 0.02 g), Pd / C (0.2 mmol, 0.02 g), and 100 mL of glacial acetic acid were added to the reaction system. The mixture was then heated to 80 °C and reacted for 12 hours. After cooling, the mixture was filtered, washed with water, dried, and purified by column chromatography to obtain intermediate P7.

[0225] Synthesis of intermediate P8:

[0226]

[0227] Under nitrogen protection, intermediate X2 (4.79 mmol, 2.7 g) and 50 mL of anhydrous diethyl ether were added sequentially to a two-necked flask at -78 °C. Then, a 1.6 M solution of n-butyllithium in n-hexane (10.07 mmol, 6.3 mL) was slowly added in portions. Next, starting material T6 (5.27 mmol, 1.5 g) was added to this solution, and the mixture was stirred at room temperature for 4 hours. After the reaction was complete, the mixture was treated with an aqueous solution of ammonium chloride and then extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by silica gel column chromatography yielded intermediate X4.

[0228] Intermediate X4 (5 mmol, 3.1 g), a mixed solution of tetrahydrofuran and ethanol (50 mL) were added sequentially to a two-necked flask. Then, Pd(OH)₂ / C (0.2 mmol, 0.02 g), Pd / C (0.2 mmol, 0.02 g), and 100 mL of glacial acetic acid were added to the reaction system. The mixture was then heated to 80 °C and reacted for 12 hours. After cooling, the mixture was filtered, washed with water, dried, and purified by column chromatography to obtain intermediate P8.

[0229] 2. Synthesis of intermediate Q

[0230] Synthesis of intermediate Q1:

[0231]

[0232] Add raw material A1 (18.4 mmol, 6.2 g) and cesium carbonate (55.2 mmol, 18.0 g) to a two-necked flask. Add 120 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add intermediate P7 (20.2 mmol, 8.3 g) under nitrogen protection. Reflux the solution under magnetic stirring for 24 hours. Cool, filter, wash with water, dry, and pass through a column to obtain intermediate Y1.

[0233]

[0234] Intermediate Y1 (5.1 mmol, 3.7 g) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 4.6 mL of n-butyllithium (1.2 M, 5.5 mmol) n-hexane solution was slowly added. After stirring at -78 °C for 2 hours, 15 mL of tetrahydrofuran solution of starting material D1 (5.5 mmol, 1.0 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 20 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 sodium bicarbonate (NaHCO3) solution. 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 Q1.

[0235] Synthesis of intermediate Q2:

[0236]

[0237] Intermediate Y1 (5.1 mmol, 3.7 g) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 4.6 mL of n-butyllithium (1.2 M, 5.5 mmol) n-hexane solution was slowly added. After stirring at -78 °C for 2 hours, 15 mL of tetrahydrofuran solution of starting material D2 (5.5 mmol, 1.6 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 20 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 Q2.

[0238] Synthesis of intermediate Q3:

[0239]

[0240] Add raw material A1 (18.4 mmol, 6.2 g) and cesium carbonate (55.2 mmol, 18.0 g) to a two-necked flask. Add 150 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 30 minutes. Add intermediate P8 (20.2 mmol, 10.0 g) under nitrogen protection. Reflux the solution under magnetic stirring for 28 hours. Cool, filter, wash with water, dry, and pass through a column to obtain intermediate Y2.

[0241]

[0242] Intermediate Y2 (5.1 mmol, 4.1 g) was dissolved in 50 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 4.6 mL of n-butyllithium (1.2 M, 5.5 mmol) n-hexane solution was slowly added. After stirring at -78 °C for 2 hours, 15 mL of tetrahydrofuran solution of starting material D1 (5.5 mmol, 1.0 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 20 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 sodium bicarbonate (NaHCO3) solution. 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 Q3.

[0243] 3. Synthesis of the Examples

[0244] Example 1: Synthesis of Compound 97:

[0245]

[0246] Intermediate Q1 (5 mmol, 3.8 g), intermediate P1 (5 mmol, 1.6 g), CuI catalyst (1 mmol, 0.2 g), and K3PO4 (25 mmol, 5.3 g) were added sequentially to a three-necked flask. Then, under a nitrogen atmosphere, trans-1,2-cyclohexanediamine (1.8 mmol, 0.2 g) and 70 mL of dioxane were added. The mixture was stirred at 110 °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 K2.

[0247]

[0248] In a three-necked flask under nitrogen protection, intermediate K2 (10 mmol, 10.0 g) and 120 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 4.8 mL) was added at -78 °C, the system was heated to 60 °C and reacted for 2.5 h. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the mixture was transferred to room temperature and reacted for another 6 h. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the mixture was heated to 200 °C and reacted for 12 h. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 97. In toluene solution (1 × 10⁻⁶ g / mL) -5 The half-width at half maximum (WHM) is 27 nm.

[0249] Example 2: Synthesis of Compound 101:

[0250]

[0251] Intermediate Q2 (5 mmol, 4.4 g), intermediate P2 (5 mmol, 2.2 g), CuI catalyst (1 mmol, 0.2 g), and K3PO4 (25 mmol, 5.3 g) were added sequentially to a three-necked flask. 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 110 °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 K3.

[0252]

[0253] In a three-necked flask under nitrogen protection, intermediate K3 (10 mmol, 12.2 g) and 150 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 4.8 mL) was added at -78 °C, the system was heated to 60 °C and reacted for 5 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the mixture was transferred to room temperature and reacted for another 8 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the mixture was heated to 200 °C and reacted for 13 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 101. In toluene solution (1 × 10⁻⁶), -5 The half-width at half maximum (WHM) is 25 nm.

[0254] Example 3: Synthesis of Compound 130:

[0255]

[0256] Intermediate Q3 (5 mmol, 4.2 g), intermediate P3 (5 mmol, 2.7 g), CuI catalyst (1 mmol, 0.2 g), and K3PO4 (25 mmol, 5.3 g) were added sequentially to a three-necked flask. 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 110 °C for 15 hours. The reaction mixture was then cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compounds were separated by silica gel column chromatography to obtain intermediate K4.

[0257]

[0258] In a three-necked flask under nitrogen protection, intermediate K4 (10 mmol, 13.1 g) and 150 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 4.8 mL) was added at -78 °C, the system was heated to 60 °C and reacted for 4 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the mixture was transferred to room temperature and reacted for another 6 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the mixture was heated to 200 °C and reacted for 15 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 130. In toluene solution (1 × 10⁻⁶), the organic layer was... -5 The half-width at half maximum (WHM) is 24 nm.

[0259] Example 4: Synthesis of Compound 159:

[0260]

[0261] Intermediate Q1 (5 mmol, 3.8 g), intermediate P4 (5 mmol, 1.6 g), CuI catalyst (1 mmol, 0.2 g), and K3PO4 (25 mmol, 5.3 g) were added sequentially to a three-necked flask. 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 110 °C for 16 hours. The reaction mixture was then cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compounds were separated by silica gel column chromatography to obtain intermediate K5.

[0262]

[0263] In a three-necked flask under nitrogen protection, intermediate K5 (10 mmol, 10.0 g) and 120 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 4.8 mL) was added at -78 °C, the system was heated to 60 °C and reacted for 2 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the mixture was transferred to room temperature and reacted for another 6 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the system was heated to 200 °C and reacted for 12 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 159. In toluene solution (1 × 10⁻⁶ g / mL) -5 The half-width at half maximum (WHM) is 25 nm.

[0264] Example 5: Synthesis of Compound 160:

[0265]

[0266] Intermediate Q1 (5 mmol, 3.8 g), intermediate P5 (5 mmol, 2.2 g), CuI catalyst (1 mmol, 0.2 g), and K3PO4 (25 mmol, 5.3 g) were added sequentially to a three-necked flask. 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 110 °C for 13 hours. The reaction mixture was then cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compounds were separated by silica gel column chromatography to obtain intermediate K6.

[0267]

[0268] In a three-necked flask under nitrogen protection, intermediate K6 (10 mmol, 11.1 g) and 120 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 4.8 mL) was added at -78 °C, the system was heated to 60 °C and reacted for 3 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the mixture was transferred to room temperature and reacted for another 6 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the mixture was heated to 200 °C and reacted for 12 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 160. In toluene solution (1 × 10⁻⁶ g / mL) -5 The half-width at half maximum (WHM) is 23 nm.

[0269] Example 6: Synthesis of compound 305:

[0270]

[0271] Intermediate Q1 (5 mmol, 3.8 g), intermediate P6 (5 mmol, 1.7 g), CuI catalyst (1 mmol, 0.2 g), and K3PO4 (25 mmol, 5.3 g) were added sequentially to a three-necked flask. 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 110 °C for 16 hours. The reaction mixture was then cooled to room temperature, diluted with toluene, filtered through silica gel, and concentrated. The compounds were separated by silica gel column chromatography to obtain intermediate K7.

[0272]

[0273] In a three-necked flask under nitrogen protection, intermediate K7 (10 mmol, 10.2 g) and 120 mL of o-dichlorobenzene were added. A 2.5 M solution of tert-butyllithium in n-hexane (12 mmol, 4.8 mL) was added at -78 °C, the system was heated to 60 °C and reacted for 2 hours. Then, boron tribromide (15 mmol, 1.5 mL) was added at 0 °C, and the reaction was continued at room temperature for 6 hours. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the system was heated to 200 °C and reacted for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to give compound 305. In toluene solution (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 24 nm.

[0274] Note: Half-width at half-maximum (FWHM) was measured using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0275] The structural characterization of the compounds obtained in each embodiment is shown in Table 1.

[0276] Table 1

[0277]

[0278] The application effects of the organic electroluminescent materials synthesized in this invention in devices are described in detail below through device examples 1-12 and device comparative examples 1-3. The fabrication processes of device examples 2-12 and device comparative examples 1-3 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 doping material in the light-emitting layer. The layer structures and test results of each device example are shown in Tables 2 and 3, respectively.

[0279] Device Example 1

[0280] 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 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Finally, a 30nm 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. GH-1 and GH-2 are used as the host materials, GD-1 as the first dopant, and compound 97 as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and compound 97 is 66.5:30:3:0.5, and the thickness of the light-emitting layer is 30 nm. After the light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer is the hole blocking layer 7. After the hole blocking layer 7, ET-1 and Liq are vacuum-deposited to a mass ratio of 1:1, with a thickness of 30 nm; this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm is fabricated by vacuum evaporation device, with a Mg:Ag mass ratio of 1:9. This layer is used as the cathode layer 10.

[0281] The molecular structural formulas of the relevant materials are shown below:

[0282]

[0283]

[0284] After completing the organic electroluminescent device as described above, the anode and cathode were connected using a known driving circuit, and the current efficiency and lifetime of the device were measured. Examples and comparative examples of devices prepared using the same method are shown in Table 2; the test results for the current efficiency and lifetime of the obtained devices are shown in Table 3.

[0285] Table 2

[0286]

[0287]

[0288] Table 3

[0289]

[0290] Note: Current efficiency and emission peak were measured using an IVL (current-voltage-brightness) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.); the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are within 10 mA / cm². 2 Next test.

[0291] As can be seen from the device data results in Table 3, the emission peak of the compound of the present invention is between 510 and 540 nm, which can achieve the effect of green light emission very well. Compared with the devices of Comparative Examples 1-3, the current efficiency and lifetime of the device with the compound of the present invention as the doping material of the light emission layer are significantly improved compared with the organic electroluminescent devices of known materials.

[0292] To compare the efficiency degradation of different devices under high current density, an efficiency degradation coefficient for each device was defined. Where μ m Expressed as the maximum current efficiency of the device, μ 50 This indicates a drive current of 50mA / cm. 2 The current efficiency of the device. A higher value indicates a more severe efficiency roll-off in the device; conversely, a lower value indicates that the rapid degradation problem at high current densities has been controlled. This invention measured the efficiency degradation coefficients of devices in Examples 1-12 and Comparative Examples 1-3. The results are shown in Table 4:

[0293] Table 4

[0294]

[0295] As shown in Table 4, compared with ref-1, ref-2 and ref-3, when the compounds of the present invention are used as doping materials for the light-emitting layer, the efficiency roll-off of the device is smaller, and the exciton quenching at high concentrations is effectively suppressed, which is beneficial to maintaining the stability of the luminescence efficiency.

[0296] 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), Z is independently represented as C-(H) or C-(R0); R0 represents a deuterium atom, a halogen atom, a cyano group, or a C1-C1 group substituted or unsubstituted with a substituent. 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted); R1 and R2 appearing the same or different each time represent hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, and 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted); R1 and R2 are either not connected or connected in a C6-C configuration with or without substituents. 30 Aromatic rings, 5-30 membered heteroaromatic rings substituted or unsubstituted, C5-C6 substituted or unsubstituted 30 Aliphatic rings; M1 represents C6 to C6, which are substituted or unsubstituted by one or more R groups. 30 The aromatic ring, or a 5-30 membered heteroaromatic ring substituted or unsubstituted with one or more Rs; Each occurrence of R, whether the same or different, represents 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of the following: aryl, 5-30 membered heteroaryl (substituted or unsubstituted), borane (substituted or unsubstituted), and silane (substituted or unsubstituted); The replacement of R is either a single bond or a parallel ring connection; Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 appearing the same or different each time indicates that C1 to C6 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, one of 5-30 membered heteroaryl groups substituted or unsubstituted, one of borane groups substituted or unsubstituted, and one of silane groups substituted or unsubstituted; Ar3 and Ar4 are either not connected or connected in a C6-C configuration with or without substituents. 30 Aromatic rings, 5-30 membered heteroaromatic rings substituted or unsubstituted, C5-C6 substituted or unsubstituted 30 Aliphatic rings; Ar5 and Ar6 are either not connected or connected in a C6-C6 configuration with or without substituents. 30 Aromatic rings, 5-30 membered heteroaromatic rings substituted or unsubstituted, C5-C6 substituted or unsubstituted 30 Aliphatic rings; Ar2 is either not connected to M1 or connected in a C6-C configuration with or without substituents. 30 Aromatic rings, 5-30 membered heteroaromatic rings substituted or unsubstituted, C5-C6 substituted or unsubstituted 30 Aliphatic rings; The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl; 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 (A-1): In general formula (A-1), the definitions of R1, R2, Ar2, Ar3, Ar4, Ar5, Ar6, M1, and Z are the same as those in general formula (1).

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 (B-1) to (B-8): In general formulas (B-1) to (B-8), the definitions of R1, R2, Ar1, Ar3, Ar4, Ar5, Ar6, and Z are the same as those in general formula (1); X1 is represented as O, S, N-(R) d ) or C(R e (R) f ); R d Represented as C6-C6 with or without substituents. 30 One of aryl, substituted or unsubstituted 5-30 heteroaryl groups; R e R f Represented as C1-C1 with or without substituents. 10 Alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl groups, 5-30 membered heteroaryl groups substituted or unsubstituted; Ar7 and Ar8 are each represented independently as C1-C1 cells with or without substituents, 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, one of 5-30 membered heteroaryl groups substituted or unsubstituted, one of borane alkyl groups substituted or unsubstituted, and one of silane alkyl groups substituted or unsubstituted; The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl; 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 (C-1) to (C-3): In general formulas (C-1) to (C-3), the definitions of R1, R2, Ar1, Ar2, M1, and Z are the same as those in general formula (1).

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 (D-1) to (D-8): In general formulas (D-1) to (D-8), the definitions of R1, R2, and Z are the same as those in general formula (1); X1 is represented as O, S, N-(R) d ) or C(R e (R) f ); R d Represented as C6-C6 with or without substituents. 30 One of aryl, substituted or unsubstituted 5-30 heteroaryl groups; R e R f Represented as C1-C1 with or without substituents. 10 Alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl groups, 5-30 membered heteroaryl groups substituted or unsubstituted; Ar7 and Ar8 are each represented independently as C1-C1 cells with or without substituents, 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, one of 5-30 membered heteroaryl groups substituted or unsubstituted, one of borane alkyl groups substituted or unsubstituted, and one of silane alkyl groups substituted or unsubstituted; The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl; 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 (E-1) to (E-12): In general formulas (E-1) to (E-12), the definitions of R1, R2, Ar1, and Ar2 are the same as those in general formula (1); X1 is represented as O, S, N-(R) d ) or C(R e (R) f ); R d Represented as C6-C6 with or without substituents. 30 One of aryl, substituted or unsubstituted 5-30 heteroaryl groups; R e R f Represented as C1-C1 with or without substituents. 10 Alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl groups, 5-30 membered heteroaryl groups substituted or unsubstituted; Ar7 and Ar8 are each represented independently as C1-C1 cells with or without substituents, 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, one of 5-30 membered heteroaryl groups substituted or unsubstituted, one of borane alkyl groups substituted or unsubstituted, and one of silane alkyl groups substituted or unsubstituted; R3, R4, R5, R6, R7, R8, R9, R 10 Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1-C 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, one of 5-30 membered heteroaryl groups substituted or unsubstituted, one of borane alkyl groups substituted or unsubstituted, and one of silane alkyl groups substituted or unsubstituted; m, n, s, k, v represent 0, 1, 2, 3, or 4; p, q, j, g represent 0, 1, 2, or 3; h represents 0, 1, 2, 3, 4 or 5; The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl; The heteroatom in 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 (F-1) to (F-8): In general formulas (F-1) to (F-8), the definitions of R1, R2, and Z are the same as those in general formula (1); X1 is represented as O, S, N-(R) d ) or C(R e (R) f ); R d Represented as C6-C6 with or without substituents. 30 One of aryl, substituted or unsubstituted 5-30 heteroaryl groups; R e R f Represented as C1-C1 with or without substituents. 10 Alkyl groups, substituted or unsubstituted C6-C6 groups 30 Aryl groups, 5-30 membered heteroaryl groups substituted or unsubstituted; Ar7 and Ar8 are each represented independently as C1-C1 cells with or without substituents, 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, one of 5-30 membered heteroaryl groups substituted or unsubstituted, one of borane alkyl groups substituted or unsubstituted, and one of silane alkyl groups substituted or unsubstituted; R3, R4, R5, R6, R7, and R8 appearing in the same or different forms each time represent hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, and 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, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 One of aryl, one of 5-30 membered heteroaryl groups substituted or unsubstituted, one of borane alkyl groups substituted or unsubstituted, and one of silane alkyl groups substituted or unsubstituted; The substituents are selected from deuterium, halogen atoms, cyano groups, C1-C2 groups. 10 Alkyl, deuterium-substituted C1-C 10 Alkyl, C3-C 10 cycloalkyl, deuterated C3-C 10 cycloalkyl, C6-C 30 Aryl and deuterium-substituted C6-C 30 Any one or more of aryl, 5-30 heteroaryl, and deuterated 5-30 heteroaryl; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

8. The boron-containing resonance-type organic compound according to any one of claims 1-7, characterized in that, M1 represents any one of the following groups, substituted or unsubstituted with R: phenyl, naphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, indole[3,2,1-jk]carbazoyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and spirofluorenyl. The R0 and R represent a deuterium atom, a halogen atom, a cyano group, 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 cyclohexyl group (substituted or unsubstituted), an adamantyl group (substituted or unsubstituted), a phenyl group (substituted or unsubstituted), a diphenyl group (substituted or unsubstituted), a terphenyl group (substituted or unsubstituted), a naphthyl group (substituted or unsubstituted), anthracene group (substituted or unsubstituted), a phenanthryl group (substituted or unsubstituted), a pyridyl group (substituted or unsubstituted), and a group (substituted or unsubstituted). Quinolinyl, furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), benzothiopheneyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiopheneyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), 9,9-diphenylfluorenyl (substituted or unsubstituted), spirofluorenyl (substituted or unsubstituted), amino (substituted or unsubstituted), triazineyl (substituted or unsubstituted). The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 Each of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, cyano group, methyl group (substituted or unsubstituted), ethyl group (substituted or unsubstituted), isopropyl group (substituted or unsubstituted), tert-butyl group (substituted or unsubstituted), cyclohexyl group (substituted or unsubstituted), adamantyl group (substituted or unsubstituted), phenyl group (substituted or unsubstituted), diphenyl group (substituted or unsubstituted), terphenyl group (substituted or unsubstituted), naphthyl group (substituted or unsubstituted), anthracene group (substituted or unsubstituted), phenanthryl group (substituted or unsubstituted), pyridyl group (substituted or unsubstituted), and [other groups, substituted or unsubstituted]. Quinolinyl, furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), benzothiopheneyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiopheneyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), 9,9-dimethylfluorenyl (substituted or unsubstituted), 9,9-diphenylfluorenyl (substituted or unsubstituted), spirofluorenyl (substituted or unsubstituted), amino (substituted or unsubstituted), triazineyl (substituted or unsubstituted). Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are independently represented as methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), adamantyl (substituted or unsubstituted), phenyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraceneyl (substituted or unsubstituted), phenanthryl (substituted or unsubstituted), pyridyl (substituted or unsubstituted), and so on. Substituent-substituted or unsubstituted quinolinyl, substituent-substituted or unsubstituted furanyl, substituent-substituted or unsubstituted thiopheneyl, substituent-substituted or unsubstituted benzofuranyl, substituent-substituted or unsubstituted benzothiopheneyl, substituent-substituted or unsubstituted dibenzofuranyl, substituent-substituted or unsubstituted dibenzothiopheneyl, substituent-substituted or unsubstituted carbazoyl, substituent-substituted or unsubstituted N-phenylcarbazoyl, substituent-substituted or unsubstituted 9,9-dimethylfluorenyl, substituent-substituted or unsubstituted 9,9-diphenylfluorenyl, substituent-substituted or unsubstituted spirofluorenyl, substituent-substituted or unsubstituted amino, substituent-substituted or unsubstituted triazineyl; The R d Represented as phenyl with or without substituents, diphenyl with or without substituents, terphenyl with or without substituents, naphthyl with or without substituents, anthraceneyl with or without substituents, phenanthryl with or without substituents, pyridyl with or without substituents, quinolinyl with or without substituents, furanyl with or without substituents, thiopheneyl with or without substituents, benzofuranyl with or without substituents, etc. Substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted N-phenylcarbazolyl group, substituted or unsubstituted 9,9-dimethylfluorenyl group, substituted or unsubstituted 9,9-diphenylfluorenyl group, substituted or unsubstituted spirofluorenyl group, substituted or unsubstituted amino group, substituted or unsubstituted triazine group; The R e R f Represented as methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), adamantyl (substituted or unsubstituted), phenyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraceneyl (substituted or unsubstituted), phenanthrene (substituted or unsubstituted), pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), and others. Substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted 9,9-dimethylfluorenyl, substituted or unsubstituted 9,9-diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazineyl; The substituents are selected from one or more of the following: deuterium, chlorine, fluorine, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridinyl, pyrazinyl, pyrazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, 9,9-dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthreneyl.

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, a second electrode, and a functional layer, wherein the functional layer is located between the first electrode and the second electrode, characterized in that: The functional layer contains the boron-containing resonance-type organic compound as described in any one of claims 1-9; Preferably, the functional layer includes a light-emitting layer, the light-emitting layer includes a host material and a dopant material, and the dopant material is a boron-containing resonant organic compound as described in any one of claims 1-9; Preferably, the functional layer includes a light-emitting layer, which includes a first host material, a second host material, and a dopant material. 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 any one of claims 1-9.

11. The organic light-emitting device according to claim 10, wherein the functional layer comprises a light-emitting layer, 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 a boron-containing resonant organic compound according to any one of claims 1-9.

Images