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

Abstract

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

Description

Technical Field

[0001] This invention relates to the field of semiconductor materials technology, and in particular 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 lighter and thinner designs, higher color contrast, lower power consumption, faster response times, higher resolution, and greater flexibility, making them poised to dominate future display terminal products. With the advent of the 5G era, the new information display industry urgently needs iterative development. Early, lower color gamut standards (BT.709 and DCI P3) can no longer meet the high-quality technological demands of display products. To achieve ultra-high definition and higher image quality performance requirements for display products, the new generation display standard (BT.2020) is driving the development of organic electroluminescent materials towards higher color purity, which requires core light-emitting materials to have a narrower emission spectrum. Currently, among the three commercially available OLED color display technologies (red, green, and blue), blue light uses traditional fluorescent triplet-triplet conversion (TTF) technology. This technology has low efficiency but high color purity, and it has basically met the BT.2020 display 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 wide emission spectrum of phosphorescence, which is far from meeting 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 < 30 nm) based on boron-nitrogen resonant structures have been reported successively, 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 this type of material, which has 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 makes full use of triplet excitons and transfers energy to fluorescent doping materials through energy transfer, which can also achieve 100% in-device quantum efficiency (DOI: 10.1038 / ncomms5016, DOI: 10.1038 / s41566-022-00958-4). This technology can make up for the shortcomings of insufficient exciton utilization of fluorescent doping materials and effectively leverage the characteristics of high fluorescence quantum yield, high device stability, high color purity and low cost of fluorescent doping materials, which has broad prospects for OLED applications. For example, CN 107507921 A and CN 110492006 A 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 110492005 A and CN 110492009 A 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 boron-containing resonant organic compound of this invention can achieve green fluorescence emission.

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

[0007] General formula (1)

[0008] In general formula (1), the occurrence of M1, M2, M3, M4, and M5 being the same or different each time is represented by C6~C. 30 Aryl or C2~C 30 Mixed aromatics;

[0009] X1 and X2 can be represented independently as either carbon atoms or silicon atoms;

[0010] R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently represented as a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a C1-C group substituted or unsubstituted with a substituent. 10 Alkyl groups, substituted or unsubstituted C3~C 10Cycloalkyl, C2-C substituted or unsubstituted 10 Alkenyl, C2~C with or without substituents 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 heteroaryl groups, C2-C substituted or unsubstituted groups 30 Boronyl groups, substituted or unsubstituted C3~C 30 One of the silane groups;

[0011] The connection methods of R1, R2, R3, R4, R5, R6, R7, and R8 are either single-key connection or parallel ring connection;

[0012] a1, a2, a3, a4, and a5 are each independently represented as 0 to the maximum allowed number of substitutions;

[0013] a6 and a8 can be independently represented as 0, 1, 2, 3 or 4;

[0014] a7 represents 0, 1, or 2;

[0015] Ar1 and Ar2 are independently represented as C3~C3 with or without R substitution. 10 Cycloalkyl, C6~C substituted or unsubstituted 30 Aryl group, C3~C group substituted or unsubstituted with R 30 Silyl, C2~C substituted or unsubstituted 30 One of the heteroaryl groups;

[0016] R represents a deuterium atom, a halogen atom, a cyano group, or a C1-C group that is substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3~C 10 Cycloalkyl, C2-C substituted or unsubstituted 10 Alkenyl, C2~C with or without substituents 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 heteroaryl, C2~C substituted or unsubstituted 30 Boronyl groups, substituted or unsubstituted C3~C 30 One of the silane groups;

[0017] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1~C1 groups. 10 Alkyl or deuterated C1~C 10 Alkyl, C3~C10 Cycloalkyl and deuterium-substituted C3~C 10 cycloalkyl, C6~C 30 Aryl and deuterium-substituted C6~C 30 Aryl, C1~C 10 Alkyl-substituted C6~C 30 Aryl, C2~C 30 heteroaryl, C3~C 30 Silyl, deuterium-substituted C2~C 30 Any one or more combinations of heteroaryl groups;

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

[0019] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (2-1) to (2-3):

[0020]

[0021] General formula (2-1) General formula (2-2)

[0022] General formula (2-3)

[0023] In general formulas (2-1) to (2-3), the definitions of M2, M3, M5, R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar1, Ar2, X1, X2, a6, a7, and a8 are the same as those in general formula (1);

[0024] a1 and a2 can be independently represented as 0, 1, 2 or 3;

[0025] a3, a4, and a5 can be independently represented as 0, 1, 2, 3, or 4.

[0026] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (3-1) to (3-13):

[0027]

[0028] General formula (3-1) General formula (3-2)

[0029]

[0030] General formula (3-3) General formula (3-4)

[0031]

[0032] General formula (3-5) General formula (3-6)

[0033]

[0034] General formula (3-7) General formula (3-8)

[0035]

[0036] General formula (3-9) General formula (3-10)

[0037]

[0038] General formula (3-11) General formula (3-12)

[0039]

[0040] General formula (3-13)

[0041] In general formulas (3-1) to (3-13), the definitions of R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar1, Ar2, X1, X2, a6, a7, and a8 are the same as those in general formula (1);

[0042] a1 and a2 can be independently represented as 0, 1, 2 or 3;

[0043] a3, a4, a5, a 10 a 11 a 12 Each can be independently represented as 0, 1, 2, 3, or 4;

[0044] a'2, a'3, a'5 represent 0, 1, 2, 3, 4, or 5;

[0045] a 13 Represented as 0, 1, or 2;

[0046] X3, X4, and X5 can be independently represented as oxygen atoms, sulfur atoms, or N(R0);

[0047] Each occurrence of R0 is independently represented as C1~C1. 10 Alkyl or deuterated 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, C1~C 10 Alkyl-substituted C6~C30 Aryl, C2~C 30 C2~C of heteroaryl and deuterium-substituted compounds 30 One of the heteroaryl groups;

[0048] R 10 R 11 R 12 R 13 Each occurrence is represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1~C with or without substituents. 10 Alkyl groups, substituted or unsubstituted C3~C 10 Cycloalkyl, C2-C substituted or unsubstituted 10 Alkenyl, C2~C with or without substituents 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 heteroaryl groups, C2-C substituted or unsubstituted groups 30 Boronyl groups, substituted or unsubstituted C3~C 30 One of the silane groups;

[0049] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1~C1 groups. 10 Alkyl or deuterated 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, C1~C 10 Alkyl-substituted C6~C 30 Aryl, C2~C 30 heteroaryl, C3~C 30 Silyl, deuterium-substituted C2~C 30 Any one or more combinations of heteroaryl groups;

[0050] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0051] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (4-1) to (4-2):

[0052]

[0053] General formula (4-1) General formula (4-2)

[0054] In general formulas (4-1) to (4-2), the definitions of R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar1, Ar2, X1, X2, a6, a7, and a8 are the same as those in general formula (1);

[0055] a3, a4, and a5 can be independently represented as 0, 1, 2, 3, or 4;

[0056] a'2 represents 0, 1, 2, 3, 4, or 5.

[0057] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (5-1) to (5-2):

[0058]

[0059] General formula (5-1) General formula (5-2)

[0060] In general formulas (5-1) to (5-2), the definitions of R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar1, Ar2, X1, X2, a6, a7, and a8 are the same as those in general formula (1);

[0061] a3, a4, and a5 can be independently represented as 0, 1, 2, 3, or 4;

[0062] a'2 represents 0, 1, 2, 3, 4, or 5.

[0063] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (6-1) to (6-13):

[0064]

[0065] General formula (6-1) General formula (6-2)

[0066]

[0067] General formula (6-3) General formula (6-4)

[0068]

[0069] General formula (6-5) General formula (6-6)

[0070]

[0071] General formula (6-7) General formula (6-8)

[0072]

[0073] General formula (6-9) General formula (6-10)

[0074]

[0075] General formula (6-11) General formula (6-12)

[0076]

[0077] General formula (6-13)

[0078] In general formulas (6-1) to (6-13), the definitions of R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar1, Ar2, X1, and X2 are the same as those in general formula (1);

[0079] X3, X4, and X5 can be independently represented as oxygen atoms, sulfur atoms, or N(R0);

[0080] Each occurrence of R0 is independently represented as C1~C1. 10 Alkyl or deuterated 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, C1~C 10 Alkyl-substituted C6~C 30 Aryl, C2~C 30 C2~C of heteroaryl and deuterium-substituted compounds 30 One of the heteroaryl groups;

[0081] R 10 R 11 R 12 R 13 Each occurrence is represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1~C with or without substituents. 10 Alkyl groups, substituted or unsubstituted C3~C 10 Cycloalkyl, C2-C substituted or unsubstituted 10 Alkenyl, C2~C with or without substituents 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30heteroaryl groups, C2-C substituted or unsubstituted groups 30 Boronyl groups, substituted or unsubstituted C3~C 30 One of the silane groups;

[0082] The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1~C1 groups. 10 Alkyl or deuterated 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, C1~C 10 Alkyl-substituted C6~C 30 Aryl, C2~C 30 heteroaryl, C3~C 30 Silyl, deuterium-substituted C2~C 30 Any one or more combinations of heteroaryl groups;

[0083] The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

[0084] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (7-1) to (7-2):

[0085]

[0086] General formula (7-1) General formula (7-2)

[0087] In general formulas (7-1) to (7-2), the definitions of R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar1, Ar2, X1, and X2 are the same as those in general formula (1).

[0088] Furthermore, the structure of the boron-containing resonance organic compound is shown in any one of general formulas (8-1) to (8-2):

[0089]

[0090] General formula (8-1) General formula (8-2)

[0091] In general formulas (8-1) to (8-2), the definitions of R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar1, Ar2, X1, and X2 are the same as those in general formula (1).

[0092] Furthermore, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 Each of these can be independently represented as a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group (substituted or unsubstituted), a methyl group (substituted or unsubstituted), an ethyl group (substituted or unsubstituted), an isopropyl group (substituted or unsubstituted), a tert-butyl group (substituted or unsubstituted), a tert-pentyl group (substituted or unsubstituted), a cyclopentyl group (substituted or unsubstituted), a cyclohexyl group (substituted or unsubstituted), a phenyl group (substituted or unsubstituted), or a dialkyl group (substituted or unsubstituted). Biphenyl, terphenyl (substituted or unsubstituted), diphenyl ether (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraceneyl (substituted or unsubstituted), phenanthryl (substituted or unsubstituted), pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted) alkyl, dibenzothiophene group (substituted or unsubstituted), carbazolyl group (substituted or unsubstituted), N-phenylcarbazolyl group (substituted or unsubstituted), 9,9-dimethylfluorenyl group (substituted or unsubstituted), diphenylfluorenyl group (substituted or unsubstituted), spirofluorenyl group (substituted or unsubstituted), xanthone group (substituted or unsubstituted), triazine group (substituted or unsubstituted), methoxy group (substituted or unsubstituted), tert-butoxy group (substituted or unsubstituted). One of the following: diphenylamino group substituted or unsubstituted; 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group substituted or unsubstituted; indole group substituted or unsubstituted; benzoindole group substituted or unsubstituted; N-phenyl-1-naphthylamino group substituted or unsubstituted; N-phenyl-2-naphthylamino group substituted or unsubstituted; trimethylsilyl group substituted or unsubstituted; and tert-butyldimethylsilyl group substituted or unsubstituted.

[0093] Ar1 and Ar2 represent methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), tert-pentyl (substituted or unsubstituted), cyclopentyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), phenyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthracene (substituted or unsubstituted), phenanthryl (substituted or unsubstituted), pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), and furfural (substituted or unsubstituted). One of the following: yl, thiophene group (substituted or unsubstituted), benzofuran 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), spirofluorenyl group (substituted or unsubstituted), xanthone group (substituted or unsubstituted), triazine group (substituted or unsubstituted), 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group (substituted or unsubstituted), indole group (substituted or unsubstituted), and benzoindole group (substituted or unsubstituted).

[0094] The R represents a deuterium atom, a halogen atom, a cyano group, an adamantyl group (substituted or unsubstituted), a methyl group (substituted or unsubstituted), an ethyl group (substituted or unsubstituted), an isopropyl group (substituted or unsubstituted), a tert-butyl group (substituted or unsubstituted), a tert-pentyl group (substituted or unsubstituted), a cyclopentyl group (substituted or unsubstituted), a cyclohexyl group (substituted or unsubstituted), a phenyl group (substituted or unsubstituted), a diphenyl group (substituted or unsubstituted), or a group composed of... Substituted or unsubstituted triphenyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl. 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 diphenylfluorenyl group, substituted or unsubstituted spirofluorenyl group, substituted or unsubstituted xanthone group, substituted or unsubstituted triazine group, substituted or unsubstituted methoxy group, substituted or unsubstituted tert-butoxy group, substituted or unsubstituted One of the following: diphenylamino group substituted or unsubstituted; 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group substituted or unsubstituted; indole group substituted or unsubstituted; benzoindole group substituted or unsubstituted; N-phenyl-1-naphthylamino group substituted or unsubstituted; N-phenyl-2-naphthylamino group substituted or unsubstituted; trimethylsilyl group substituted or unsubstituted; and tert-butyldimethylsilyl group substituted or unsubstituted.

[0095] The R0 represents one of the following: adamantyl, methyl, ethyl, isopropyl, tert-butyl, tert-pentyl, cyclopentyl, cyclohexyl, phenyl, diphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, xanthonel, triazine, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, indolyl, benzoindolyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, and tert-butyl-substituted diphenyl.

[0096] M1, M2, M3, M4, and M5 represent one of the following: phenyl, diphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, indoleyl, and benzoindoleyl.

[0097] The substituents used for the substituent groups are selected from deuterium, chlorine, fluorine, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, phenyl, diphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiophene, indoleyl, pyrroleyl, and dibenzofuranyl. Dibenzothiophene, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, azirphenanthrenel, diphenylamino, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, benzoindolyl, deuterated adamantyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated tert-amyl, deuterated tert-butyl, deuterated... Butyl, deuterated phenyl, deuterated diphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated pyridazinyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated quinoxalinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated furanyl, deuterated thiopheneyl, deuterated indole One or more of the following: dolomyl, deuterated pyrroleyl, deuterated dibenzofuranyl, deuterated dibenzothiopheneyl, deuterated 9,9-dimethylfluorenyl, deuterated spirofluorenyl, deuterated carbazolyl, deuterated N-phenylcarbazolyl, deuterated carbazolinyl, deuterated azirophenonel, deuterated 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and deuterated benzoindolyl.

[0098] Furthermore, the specific structural formula of the boron-containing resonance organic compound is any one of the following structures:

[0099] (1) (2) (3)

[0100] (4) (5) (6)

[0101] (7) (8) (9)

[0102] (10) (11) (12)

[0103] (13) (14) (15)

[0104] (16) (17) (18)

[0105] (19) (20) (21)

[0106] (22) (23) (24)

[0107] (25) (26) (27)

[0108] (28) (29) (30)

[0109] (31) (32) (33)

[0110] (34) (35) (36)

[0111] (37) (38) (39)

[0112] (40) (41) (42)

[0113] (43) (44) (45)

[0114] (46) (47) (48)

[0115] (49) (50) (51)

[0116] (52) (53) (54)

[0117] (55) (56) (57)

[0118] (58) (59) (60)

[0119] (61) (62) (63)

[0120] (64) (65) (66)

[0121] (67) (68) (69)

[0122] (70) (71) (72)

[0123] (73) (74) (75)

[0124] (76) (77) (78)

[0125] (79) (80) (81)

[0126] (82) (83) (84)

[0127] (85) (86) (87)

[0128] (88) (89) (90)

[0129] (91) (92) (93)

[0130] (94) (95) (96)

[0131] (97) (98) (99)

[0132] (100) (101) (102)

[0133] (103) (104) (105)

[0134] (106) (107) (108)

[0135] (109) (110) (111)

[0136] (112) (113) (114)

[0137] (115) (116) (117)

[0138] (118) (119) (120)

[0139] (121) (122) (123)

[0140] (124) (125) (126)

[0141] (127) (128) (129)

[0142] (130) (131) (132)

[0143] (133) (134) (135)

[0144] (136) (137) (138)

[0145] (139) (140) (141)

[0146] (142) (143) (144)

[0147] (145) (146) (147)

[0148] (148) (149) (150)

[0149] (151) (152) (153)

[0150] (154) (155) (156)

[0151] (157) (158) (159)

[0152] (160) (161) (162)

[0153] (163) (164) (165)

[0154] (166) (167) (168)

[0155] (169) (170) (171)

[0156] (172) (173) (174)

[0157] (175) (176) (177)

[0158] (178) (179) (180)

[0159] (181) (182) (183)

[0160] (184) (185) (186)

[0161] (187) (188) (189)

[0162] (190) (191) (192)

[0163] (193) (194) (195)

[0164] (196) (197) (198)

[0165] (199) (200) (201)

[0166] (202) (203) (204)

[0167] (205) (206) (207)

[0168] (208) (209) (210)

[0169] (211) (212) (213)

[0170] (214) (215) (216)

[0171] (217) (218) (219)

[0172] (220) (221) (222)

[0173] (223) (224) (225)

[0174] (226) (227) (228)

[0175] (229) (230) (231)

[0176] (232) (233) (234)

[0177] (235) (236) (237)

[0178] (238) (239) (240)

[0179] (241) (242) (243)

[0180] (244) (245) (246)

[0181] (247) (248) (249)

[0182] (250) (251) (252)

[0183] (253) (254) (255)

[0184] (256) (257) (258)

[0185] (259) (260) (261)

[0186] (262) (263) (264)

[0187] (265) (266) (267)

[0188] (268) (269) (270)

[0189] (271) (272) (273)

[0190] (274) (275) (276)

[0191] (277) (278) (279)

[0192] (280) (281) (282)

[0193] (283) (284) (285)

[0194] (286) (287) (288)

[0195] (289) (290) (291)

[0196] (292) (293) (294)

[0197] (295) (296) (297)

[0198] (298) (299) (300)

[0199] (301) (302) (303)

[0200] (304) (305) (306)

[0201] (307) (308) (309)

[0202] (310) (311) (312)

[0203] (313) (314) (315)

[0204] (316) (317) (318)

[0205] (319) (320) (321)

[0206] (322) (323) (324)

[0207] (325) (326) (327)

[0208] (328) (329) (330)

[0209] (331) (332) (333)

[0210] (334) (335) (336)

[0211] (337) (338) (339)

[0212] (340) (341) (342)

[0213] (343) (344) (345)

[0214] (346) (347) (348)

[0215] (349) (350) (351)

[0216] (352) (353) (354)

[0217] (355) (356) (357)

[0218] (358) (359) (360)

[0219] (361) (362) (363)

[0220] (364) (365) (366)

[0221] (367) (368) (369)

[0222] (370) (371) (372)

[0223] (373) (374) (375)

[0224] (376) (377) (378)

[0225] (379) (380) (381)

[0226] (382) (383) (384)

[0227] (385) (386) (387)

[0228] (388) (389) (390)

[0229] (391) (392) (393)

[0230] (394) (395) (396)

[0231] (397) (398) (399)

[0232] (400) (401) (402)

[0233] (403) (404) (405)

[0234] (406) (407) (408)

[0235] (409) (410) (411)

[0236] (412) (413) (414)

[0237] (415) (416) (417)

[0238] (418) (419) (420)

[0239] (421) (422) (423)

[0240] (424) (425) (426)

[0241] (427) (428) (429)

[0242] (430) (431) (432)

[0243] (433) (434) (435)

[0244] (436) (437) (438)

[0245] (439) (440) (441)

[0246] (442) (443) (444)

[0247] (445) (446) (447)

[0248] (448) (449) (450)

[0249] (451) (452) (453)

[0250] (454) (455) (456)

[0251] (457) (458)。

[0252] The present invention also provides an organic light-emitting device, comprising a substrate, a first electrode, an organic functional material layer, and a second electrode, wherein the first electrode is located on the substrate, the organic functional material layer is located on the first electrode, the second electrode is located on the functional layer, and the organic functional material layer contains the boron-containing resonant organic compound.

[0253] Preferably, the organic functional material layer includes a light-emitting layer, which includes a host material and a dopant material, wherein the dopant material is the boron-containing resonant organic compound.

[0254] Furthermore, the light-emitting layer comprises a first host material, a second host material, and a dopant material, wherein at least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-containing resonant organic compound.

[0255] Furthermore, the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material. The exciton-sensitizing material is a complex containing a metal element, and the dopant material is the aforementioned boron-containing resonant organic compound.

[0256] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0257] (1) The boron-containing resonant organic compound of the present invention can be used as a doping material for organic electroluminescent devices. Under the action of an electric field, it can emit green fluorescence and can be applied to OLED lighting or OLED display fields.

[0258] (2) The boron-containing resonant organic compound of the present invention has a narrower FWHM spectrum, which can effectively improve the color gamut of the device.

[0259] (3) The boron-containing resonant organic compound of the present invention can significantly improve device efficiency and device life as a green light doping material. Attached Figure Description

[0260] Figure 1 This is a schematic diagram of the structure of an organic electroluminescent device using the materials listed in this invention;

[0261] 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

[0262] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0263] 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.

[0264] In this invention, the substituted or unsubstituted aromatic amino group refers to... Wherein Q1 and Q2 represent aromatic groups that are substituted or unsubstituted, and Q1 and Q2 preferably represent C6~C6 groups that are substituted or unsubstituted. 30 The aryl group may be substituted or unsubstituted at C2-C. 30 Mixed aromatic compounds.

[0265] In this invention, the C3~C groups, whether substituted or unsubstituted, are... 30 Silyl refers to Q3, Q4, and Q5 represent C1-C1 cells that are substituted or unsubstituted. 10 Alkyl groups or C3-C groups substituted or unsubstituted 10 Cycloalkyl groups, preferably C3-C6 substituted or unsubstituted. 10 Silyl group.

[0266] In this invention, C3~C 30 Silyl refers to Q3, Q4, and Q5 represent C1 to C2. 10 Alkyl or C3~C 10 Cycloalkyl groups, preferably C3~C 10 Silyl group.

[0267] In this invention, the C2~C groups that are substituted or unsubstituted by substituents... 30 Boronyl refers to Q6 and Q7 represent C1-C1 cells that are substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3~C 10 Cycloalkyl, C6~C6 substituted or unsubstituted 30 Aryl, substituted or unsubstituted C2~C 30 Mixed aromatic compounds.

[0268] In this invention, the C6~C groups, whether substituted or unsubstituted, are... 30Aryl refers to an aryl group having 6 to 30 carbon atoms, either substituted or unsubstituted, preferably an aryl group having 6 to 18 carbon atoms, preferably an aryl group having 6 to 12 carbon atoms, preferably a phenyl group, a naphthyl group, a diphenyl group, a terphenyl group, an anthracene group, a phenanthryl group, or a group with substituted or unsubstituted carbon atoms. Dimethylfluorenyl, diphenylfluorenyl substituted or unsubstituted, spirofluorenyl substituted or unsubstituted, fused tetraphenyl substituted or unsubstituted, pyrene substituted or unsubstituted, thionyl substituted or unsubstituted, triphenyl substituted or unsubstituted, peryl substituted or unsubstituted, indene substituted or unsubstituted, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl substituted or unsubstituted, combinations thereof, or fused rings of the foregoing groups, but not limited thereto.

[0269] In this invention, C6~C 30 Aryl refers to an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 18 carbon atoms, more preferably an aryl group having 6 to 12 carbon atoms, and preferably phenyl, naphthyl, diphenyl, terphenyl, anthracene, phenanthrene, dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, fused tetraphenyl, pyrene, phenyl, triphenylene, peryl, indene, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, or a combination thereof or a fused ring of the aforementioned groups, but is not limited thereto.

[0270] In this invention, the deuterium-substituted C6~C 30 The aryl group refers to a deuterated aryl group having 6 to 30 carbon atoms, preferably a deuterated aryl group having 6 to 18 carbon atoms, preferably a deuterated aryl group having 6 to 12 carbon atoms, preferably a deuterated phenyl group, a deuterated naphthyl group, a deuterated diphenyl group, a deuterated terphenyl group, a deuterated anthracene group, a deuterated phenanthyl group, a deuterated dimethylfluorenyl group, a deuterated diphenylfluorenyl group, a deuterated spirofluorenyl group, a deuterated fused tetraphenyl group, a deuterated pyrene group, a deuterated alkyl group, a deuterated triphenyl group, a deuterated perylyl group, a deuterated indyl group, a deuterated 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group, or a combination thereof or a fused ring of the aforementioned groups, but is not limited thereto.

[0271] In this invention, the C2~C groups that are substituted or unsubstituted by substituents... 30A heteroaryl group refers to a heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted, preferably a heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted, preferably a heteroaryl group having 4 to 20 carbon atoms substituted or unsubstituted, preferably a heteroaryl group having 4 to 12 carbon atoms substituted or unsubstituted, preferably a heteroaryl group having 5 to 12 carbon atoms substituted or unsubstituted, preferably a furanyl group substituted or unsubstituted, a thiophene group substituted or unsubstituted, or a pyridine group substituted or unsubstituted. Pyrazolyl, pyrazolyl (substituted or unsubstituted), imidazolyl (substituted or unsubstituted), triazolyl (substituted or unsubstituted), oxazolyl (substituted or unsubstituted), thiazolyl (substituted or unsubstituted), oxadiazolyl (substituted or unsubstituted), thiadiazolyl (substituted or unsubstituted), pyridyl (substituted or unsubstituted), pyrimidinyl (substituted or unsubstituted), pyrazinyl (substituted or unsubstituted), triazineyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), and so on. Substituents: benzothiophene group (substituted or unsubstituted), benzimidazolyl group (substituted or unsubstituted), indolyl group (substituted or unsubstituted), quinolinyl group (substituted or unsubstituted), isoquinolinyl group (substituted or unsubstituted), quinazolinyl group (substituted or unsubstituted), quinoxolinyl group (substituted or unsubstituted), quinoxalolinyl group (substituted or unsubstituted), naphthidyl group (substituted or unsubstituted), benzoxazinyl group (substituted or unsubstituted), benzothiazinyl group (substituted or unsubstituted), and others. Benzopyrimidinyl, acridineyl (substituted or unsubstituted), phenazinyl (substituted or unsubstituted), phenthiazinyl (substituted or unsubstituted), phenoxazinyl (substituted or unsubstituted), fumonyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted), dibenzothiopheneyl (substituted or unsubstituted), carbazoyl (substituted or unsubstituted), N-phenylcarbazoyl (substituted or unsubstituted), benzoindolyl (substituted or unsubstituted), combinations thereof, or fused rings of the foregoing groups, but not limited thereto.

[0272] In this invention, C2~C 30Heteroaryl refers to a heteroaryl group having 2 to 30 carbon atoms, preferably a heteroaryl group having 2 to 20 carbon atoms, preferably a heteroaryl group having 4 to 20 carbon atoms, preferably a heteroaryl group having 4 to 12 carbon atoms, preferably a heteroaryl group having 5 to 12 carbon atoms, preferably furanyl, thiophene, pyrrole, pyrazolyl, imidazolyl, triazolyl, oxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, pyrazinyl, etc. Triazinyl, benzofuranyl, benzothiophenyl, benzoimidazolyl, indolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinolinyl, quinoxolinyl, naphridinyl, benzooxazinyl, benzothiazinyl, benzopyrimidinyl, acridineyl, phenazinyl, phenthiazinyl, phenoxazinyl, fumonyl, dibenzofuranyl, dibenzothiaphenyl, carbazoleyl, N-phenylcarbazoleyl, benzoindolyl, fused rings of combinations thereof or combinations of the foregoing groups, but not limited thereto.

[0273] In this invention, the deuterium-substituted C2~C 30 The heteroaryl group refers to a heteroaryl group with 2 to 30 deuterated carbon atoms, preferably a heteroaryl group with 2 to 20 deuterated carbon atoms, preferably a heteroaryl group with 4 to 12 deuterated carbon atoms, preferably a heteroaryl group with 5 to 12 deuterated carbon atoms, preferably deuterated furanyl, deuterated thiophene, deuterated pyrrole, deuterated pyrazolyl, deuterated imidazolyl, deuterated triazolyl, deuterated oxazolyl, deuterated thiazolyl, deuterated oxadiazolyl, deuterated thiadiazolyl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated triazinyl, deuterated benzofuranyl, deuterated benzo[a] Thiopheneyl, deuterated benzimidazolyl, deuterated indolyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated quinazolinyl, deuterated quinolinyl, deuterated quinoxolinyl, deuterated naphthidyl, deuterated benzoxazinyl, deuterated benzothiazinyl, deuterated benzopyrimidyl, deuterated acridineyl, deuterated phenazinyl, deuterated phenthiazinyl, deuterated phenoxazinyl, deuterated fumonyl, deuterated dibenzofuranyl, deuterated dibenzothiophenyl, deuterated carbazoyl, deuterated substituted N-phenylcarbazoyl, deuterated benzoindolyl, combinations thereof, or combinations of the foregoing groups, but not limited to these.

[0274] In this invention, the number of heteroatoms in the heteroaryl group is 1-5, preferably 1-4, preferably 1-3, preferably 1-2, and preferably 1.

[0275] In this invention, the C1~C1 groups, whether substituted or unsubstituted, are... 10Alkyl groups (including straight-chain alkyl and branched-chain alkyl) refer to alkyl groups having 1 to 10 carbon atoms, substituted or unsubstituted, preferably alkyl groups having 1 to 6 carbon atoms, preferably alkyl groups having 1 to 5 carbon atoms, preferably alkyl groups having 1 to 4 carbon atoms, preferably methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, etc., substituted or unsubstituted. Isobutyl, sec-butyl (substituted or unsubstituted), neopentyl (substituted or unsubstituted), n-pentyl (substituted or unsubstituted), isopentyl (substituted or unsubstituted), tert-pentyl (substituted or unsubstituted), octyl (substituted or unsubstituted), heptyl (substituted or unsubstituted), n-decyl (substituted or unsubstituted), 1-methylpentyl (substituted or unsubstituted), 2-methylpentyl (substituted or unsubstituted), 3-methylpentyl (substituted or unsubstituted), 1-butylpentyl (substituted or unsubstituted), 2-methylbutyl (substituted or unsubstituted), etc., but not limited to these.

[0276] In this invention, C1~C 10 Alkyl (including straight-chain alkyl and branched-chain alkyl) refers to an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 6 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, preferably methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, tert-pentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, 2-methylbutyl, etc., but not limited to these.

[0277] In this invention, the deuterium-substituted C1~C 10 Alkyl groups (including straight-chain alkyl groups and branched alkyl groups) refer to deuterated alkyl groups having 1 to 10 carbon atoms, preferably deuterated alkyl groups having 1 to 6 carbon atoms, preferably deuterated alkyl groups having 1 to 5 carbon atoms, preferably deuterated alkyl groups having 1 to 4 carbon atoms, preferably deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated butyl, or deuterated tert-butyl. Butyl, deuterium-substituted isobutyl, deuterium-substituted sec-butyl, deuterium-substituted neopentyl, deuterium-substituted n-pentyl, deuterium-substituted isopentyl, deuterium-substituted tert-pentyl, deuterium-substituted octyl, deuterium-substituted heptyl, deuterium-substituted n-decyl, deuterium-substituted 1-methylpentyl, deuterium-substituted 2-methylpentyl, deuterium-substituted 3-methylpentyl, deuterium-substituted 1-butylpentyl, deuterium-substituted 2-methylbutyl, etc., but not limited to these.

[0278] In this invention, the C2~C groups that are substituted or unsubstituted by substituents... 10 The alkynyl group refers to an alkynyl group having 2 to 10 carbon atoms substituted or unsubstituted by a substituent, preferably an alkynyl group having 2 to 6 carbon atoms substituted or unsubstituted by a substituent, preferably an alkynyl group having 2 to 5 carbon atoms substituted or unsubstituted by a substituent, preferably an alkynyl group having 2 to 4 carbon atoms substituted or unsubstituted by a substituent, preferably an ethynyl group substituted or unsubstituted by a substituent, a propynyl group substituted or unsubstituted by a substituent, a 1-propynyl group substituted or unsubstituted by a substituent, a 1-butynyl group substituted or unsubstituted by a substituent, a 2-butynyl group substituted or unsubstituted by a substituent, a 3-methyl-1-propynyl group substituted or unsubstituted by a substituent, etc., but is not limited thereto.

[0279] In this invention, the C3~C groups, whether substituted or unsubstituted, are... 10 Cycloalkyl refers to monocyclic or polycyclic alkyl groups comprising 3 to 10 cyclic atoms, with or without substituted substituents, where the rings can be linked by single bonds or cyclic fusion. In this document, C4-C6 alkyl groups, with or without substituted substituents, are preferred. 10 Cycloalkyl groups, more preferably C5-C substituted or unsubstituted, are preferred. 10 Cycloalkyl groups, non-limiting examples of which may include cyclopropyl groups substituted or unsubstituted with substituents, cyclobutyl groups substituted or unsubstituted with substituents, cyclopentyl groups substituted or unsubstituted with substituents, cyclohexyl groups substituted or unsubstituted with substituents, 4-methylcyclohexyl groups substituted or unsubstituted with substituents, 4,4-dimethylcyclohexyl groups substituted or unsubstituted with substituents, adamantyl groups substituted or unsubstituted with substituents, cycloheptyl groups substituted or unsubstituted with substituents, etc., but are not limited thereto.

[0280] In this invention, C3~C 10 Cycloalkyl refers to a monocyclic or polycyclic alkyl group comprising 3 to 10 cyclic atoms, with the rings linked by single bonds or fused rings. In this document, C4-C is preferred. 10 Cycloalkyl, more preferably C5-C 10 Cycloalkyl groups, non-limiting examples of which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl, but are not limited thereto.

[0281] In this invention, the deuterium-substituted C3~C 10Cycloalkyl refers to a deuterated 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 C5-C8 cycloalkyl groups, and particularly preferably 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.

[0282] In this invention, the halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0283] In this invention, the C1~C1 groups, whether substituted or unsubstituted, are... 10 Alkoxy groups include, but are not limited to, methoxy groups substituted or unsubstituted with substituents, ethoxy groups substituted or unsubstituted with substituents, propoxy groups substituted or unsubstituted with substituents, butoxy groups substituted or unsubstituted with substituents, pentoxy groups substituted or unsubstituted with substituents, hexoxy groups substituted or unsubstituted with substituents, or isopropoxy groups substituted or unsubstituted with substituents.

[0284] In this invention, the C2~C groups that are substituted or unsubstituted by substituents... 10 Alkenyl refers to vinyl groups that are substituted or unsubstituted with substituents, allyl groups that are substituted or unsubstituted with substituents, 1-butenyl groups that are substituted or unsubstituted with substituents, 2-butenyl groups that are substituted or unsubstituted with substituents, 3-butenyl groups that are substituted or unsubstituted with substituents, 1,3-butadienyl groups that are substituted or unsubstituted with substituents, 1-methyl vinyl groups that are substituted or unsubstituted with substituents, styryl groups that are substituted or unsubstituted with substituents, 2,2-diphenyl vinyl groups that are substituted or unsubstituted with substituents, 1,2-diphenyl vinyl groups that are substituted or unsubstituted with substituents, and others. Substituted or unsubstituted 1,1-dimethylallyl, 1-methylallyl substituted or unsubstituted by a substituent, 2-methylallyl substituted or unsubstituted by a substituent, 1-phenylallyl substituted or unsubstituted by a substituent, 2-phenylallyl substituted or unsubstituted by a substituent, 3,3-diphenylallyl substituted or unsubstituted by a substituent, 1,2-dimethylallyl substituted or unsubstituted by a substituent, 1-phenyl-1-butenyl substituted or unsubstituted by a substituent, and 3-phenyl-1-butenyl substituted or unsubstituted by a substituent, etc., but not limited thereto.

[0285] In this invention, the substituents are selected from deuterium, chlorine, fluorine, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, phenyl, diphenyl, naphthyl, anthracene, phenanthrene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiophene, indoleyl, pyrroleyl, and dibenzofuranyl. Dibenzothiophene, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, azirphenanthrenel, diphenylamino, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, benzoindolyl, deuterated adamantyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated tert-amyl, deuterated tert-butyl, deuterated... Butyl, deuterated phenyl, deuterated diphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated pyridazinyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated quinoxalinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated furanyl, deuterated thiopheneyl, deuterated indole One or more of the following: dolomyl, deuterated pyrroleyl, deuterated dibenzofuranyl, deuterated dibenzothiopheneyl, deuterated 9,9-dimethylfluorenyl, deuterated spirofluorenyl, deuterated carbazolyl, deuterated N-phenylcarbazolyl, deuterated carbazolinyl, deuterated azirophenonel, deuterated 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and deuterated benzoindolyl.

[0286] The organic electroluminescent device of the present invention can be a bottom-emitting device or a top-emitting device, and there is no particular limitation thereto.

[0287] 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.

[0288] A first electrode is formed on a substrate. The first electrode and a second electrode may be opposite each other. The first electrode may be an anode, 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, typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0289] 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.

[0290] 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.

[0291] 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.

[0292] 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 functional material layer, the HOMO level of the host organic material used in the hole injection layer must possess certain characteristics with the p-doped material. This is necessary to enable charge transfer states between the host organic material and the doped material, achieving ohmic contact between the hole injection layer and the anode, and thus enabling efficient hole injection from the electrode to the hole injection layer.

[0293] 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.

[0294] Preferably, the main organic material used as the hole injection layer of the present invention may be selected from the following prior art:

[0295] The compounds disclosed in JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, and CN105439999A, but not limited thereto.

[0296] 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.

[0297] 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.

[0298] 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.

[0299] Preferably, the hole transport layer material of the present invention may be selected from the following compounds disclosed in the prior art: JP1996048656A, CN1702065A, CN101535256A, CN103108859A, US20120112176A1, JP1989142657A, CN103108859A, CN105439999A, etc.;

[0300] Preferably, the hole transport layer material of the present invention may be selected from compounds represented by the following general formula:

[0301]

[0302] Wherein, L'1 represents a single bond, a phenylene substituted or unsubstituted, a naphthylene substituted or unsubstituted, a diphenylene substituted or unsubstituted, or a terphenylene substituted or unsubstituted;

[0303] Cy1 and Cy2 represent phenyl groups substituted or unsubstituted with substituents, naphthyl groups substituted or unsubstituted with substituents, diphenyl groups substituted or unsubstituted with substituents, terphenyl groups substituted or unsubstituted with substituents, dimethylfluorenyl groups substituted or unsubstituted with substituents, diphenylfluorenyl groups substituted or unsubstituted with substituents, spirofluorenyl groups substituted or unsubstituted with substituents, dibenzofuranyl groups substituted or unsubstituted with substituents, dibenzothiophenyl groups substituted or unsubstituted with substituents, benzodibenzothiophenyl groups substituted or unsubstituted with substituents, carbazoyl groups substituted or unsubstituted with substituents, and N-phenylcarbazoyl groups substituted or unsubstituted with substituents.

[0304] R''1、R' '2 R''3 represents a hydrogen atom, a deuterium atom, a methyl group substituted or unsubstituted with a substituent, an ethyl group substituted or unsubstituted with a substituent, a propyl group substituted or unsubstituted with a substituent, an isopropyl group substituted or unsubstituted with a substituent, a butyl group substituted or unsubstituted with a substituent, a tert-butyl group substituted or unsubstituted with a substituent, a neopentyl group substituted or unsubstituted with a substituent, a n-pentyl group substituted or unsubstituted with a substituent, an isopentyl group substituted or unsubstituted with a substituent, a tert-pentyl group substituted or unsubstituted with a substituent, a phenyl group substituted or unsubstituted with a substituent, a naphthyl group substituted or unsubstituted with a substituent, a diphenyl group substituted or unsubstituted with a substituent, a terphenyl group substituted or unsubstituted with a substituent, a dimethylfluorenyl group substituted or unsubstituted with a substituent, a diphenylfluorenyl group substituted or unsubstituted with a substituent, and a spirofluorenyl group substituted or unsubstituted with a substituent.

[0305] The substituents are selected from deuterium, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, phenyl, diphenyl, and naphthyl.

[0306] Preferably, the hole transport layer material of the present invention may be selected from the compounds disclosed in the prior art:

[0307]

[0308] 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.

[0309] 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.

[0310] Preferably, the electron blocking layer material of the present invention may be selected from the following compounds disclosed in the prior art: CN102046613A, CN105408448A, KR1020160049955A, CN104114672A, KR1020130106255A, EP2922932A1, CN102224150A, US20170018710A1, WO2021214348A2, JP2023036703A, CN111146349A, CN117720422A, etc.;

[0311] Preferably, the electron blocking layer material of the present invention may be selected from compounds represented by the following general formula:

[0312]

[0313] Wherein, L'1, L'2, and L'3 represent single bonds, phenylene with or without substituents, naphthylene with or without substituents, diphenylene with or without substituents, and terphenylene with or without substituents;

[0314] Cy1 and Cy2 represent phenyl groups substituted or unsubstituted with substituents, naphthyl groups substituted or unsubstituted with substituents, diphenyl groups substituted or unsubstituted with substituents, terphenyl groups substituted or unsubstituted with substituents, dimethylfluorenyl groups substituted or unsubstituted with substituents, diphenylfluorenyl groups substituted or unsubstituted with substituents, spirofluorenyl groups substituted or unsubstituted with substituents, dibenzofuranyl groups substituted or unsubstituted with substituents, dibenzothiophenyl groups substituted or unsubstituted with substituents, benzodibenzothiophenyl groups substituted or unsubstituted with substituents, carbazoyl groups substituted or unsubstituted with substituents, and N-phenylcarbazoyl groups substituted or unsubstituted with substituents.

[0315] X1'' and X2'' can be independently represented as C(R''1)(R''2).

[0316] R''1、R' '2 It is represented as methyl with or without a substituent, or phenyl with or without a substituent;

[0317] R''1 and R' '2 They can be connected via a single key;

[0318] The substituents are selected from deuterium, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, phenyl, diphenyl, and naphthyl.

[0319] In one embodiment of the present invention, the electron blocking layer material may be selected from the compounds disclosed in the prior art:

[0320]

[0321] 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.

[0322] 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.

[0323] 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.

[0324] The light-emitting layer can contain a single-substrate material or a dual-substrate material;

[0325] Preferably, the dual-body material comprises an electronic-type body material and a hole-type body material.

[0326] 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;

[0327] 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 maximizing the exciton utilization rate of electrogenerated excitons within the device to nearly 100%. Compared to traditional fluorescent materials, TADF materials exhibit higher exciton utilization.

[0328] The light-emitting layer may include a host material, an exciton-sensitizing material, and a dopant material;

[0329] 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 resonant 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.

[0330] 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.

[0331] 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.

[0332] 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.

[0333] A hole blocking layer is a layer that prevents holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the device's lifetime and improving its performance.

[0334] Preferably, the hole-blocking layer material of the present invention may be selected from the following compounds disclosed in the prior art: JP2015111679A, KR1020180043220A, CN109564982A, KR1020180065246A, CN104487432A, CN108290854A, CN112236879A, JP2017517486A, CN116023344A, CN116969928A, etc.;

[0335] Preferably, the hole-blocking layer material of the present invention may be selected from compounds represented by the following general formula:

[0336]

[0337] Wherein, L'1, L'2, and L'3 represent single bonds, phenylene with or without substituents, naphthylene with or without substituents, diphenylene with or without substituents, and terphenylene with or without substituents;

[0338] X''1 represents non-existence, a single bond, an oxygen atom, or a sulfur atom;

[0339] X''2 represents a single bond, an oxygen atom, or a sulfur atom;

[0340] Cb1, Cb2, and Cb3 represent benzene rings substituted or unsubstituted with substituents, and naphthalene rings substituted or unsubstituted with substituents;

[0341] Cy1, Cy2, Cy3, and Cy4 represent phenyl groups substituted or unsubstituted with substituents, naphthyl groups substituted or unsubstituted with substituents, diphenyl groups substituted or unsubstituted with substituents, terphenyl groups substituted or unsubstituted with substituents, dimethylfluorenyl groups substituted or unsubstituted with substituents, diphenylfluorenyl groups substituted or unsubstituted with substituents, spirofluorenyl groups substituted or unsubstituted with substituents, dibenzofuranyl groups substituted or unsubstituted with substituents, dibenzothiophenyl groups substituted or unsubstituted with substituents, benzodibenzothiophenyl groups substituted or unsubstituted with substituents, carbazoyl groups substituted or unsubstituted with substituents, and N-phenylcarbazoyl groups substituted or unsubstituted with substituents.

[0342] The substituents are selected from deuterium, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, phenyl, diphenyl, and naphthyl.

[0343] As the hole-blocking layer material of the organic electroluminescent device of the present invention, compounds with hole-blocking properties known in the prior art can be used, for example:

[0344]

[0345] 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.

[0346] 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 them to the light-emitting layer. Materials with high electron mobility are preferred.

[0347] Preferably, the electron transport layer material of the present invention may be selected from the following compounds disclosed in the prior art: CN1784388A, CN1625552A, CN107431141A, CN107431141A, KR1020160149041A, WO2018182145A1, CN103827256A, KR101847347B1, KR1020190050658A, CN102574813A, CN107721979A, KR1020100073954A, CN110753687A, CN117999260A, CN116368126A, etc.;

[0348] Preferably, the electron transport layer material of the present invention may be selected from compounds represented by the following general formula:

[0349]

[0350] Wherein, L'1, L'2, and L'3 represent single bonds, phenylene with or without substituents, naphthylene with or without substituents, diphenylene with or without substituents, and terphenylene with or without substituents;

[0351] X''1 represents non-existence, a single bond, an oxygen atom, or a sulfur atom;

[0352] X''2 represents a single bond, an oxygen atom, or a sulfur atom;

[0353] Cb1, Cb2, and Cb3 represent benzene rings substituted or unsubstituted with substituents, and naphthalene rings substituted or unsubstituted with substituents;

[0354] Cy1, Cy2, Cy3, and Cy4 represent phenyl groups substituted or unsubstituted with substituents, naphthyl groups substituted or unsubstituted with substituents, diphenyl groups substituted or unsubstituted with substituents, terphenyl groups substituted or unsubstituted with substituents, dimethylfluorenyl groups substituted or unsubstituted with substituents, diphenylfluorenyl groups substituted or unsubstituted with substituents, spirofluorenyl groups substituted or unsubstituted with substituents, dibenzofuranyl groups substituted or unsubstituted with substituents, dibenzothiophenyl groups substituted or unsubstituted with substituents, benzodibenzothiophenyl groups substituted or unsubstituted with substituents, carbazoyl groups substituted or unsubstituted with substituents, and N-phenylcarbazoyl groups substituted or unsubstituted with substituents.

[0355] The substituents are selected from deuterium, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, phenyl, diphenyl, and naphthyl.

[0356] As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials for organic electroluminescent devices disclosed in the prior art can be used, for example:

[0357]

[0358] 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.

[0359] 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.

[0360] 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.

[0361] 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.

[0362] The second electrode can be disposed above the electron transport region. The second electrode can be a cathode, a transmission electrode, a semi-transmission electrode, or a reflection electrode. When the second electrode is a transmission electrode, it can include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF2, Ba, Ag, or compounds or mixtures thereof. When the second electrode is a semi-transmission electrode or a reflection electrode, it can include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, Mo, Ti, or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0363] 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.

[0364] 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.

[0365] Synthesis Examples

[0366] All raw materials involved in the synthesis embodiments of the present invention can be purchased from the market or obtained by conventional preparation methods in the art;

[0367] Synthesis of intermediate C-1:

[0368]

[0369] Add raw material B-1 (25 mmol, 4.46 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 110 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 1.6 hours. Add raw material A-1 (25 mmol, 8.29 g) under nitrogen protection and stir at 140 °C for 17 hours under nitrogen protection. Filter, wash with water, dry, and pass through a column to obtain intermediate C-1.

[0370] Synthesis of intermediate C-2:

[0371]

[0372] The synthesis of intermediate C-2 is similar to that of intermediate C-1, except that raw material B-2 is used instead of raw material B-1.

[0373] Synthesis of intermediate C-3:

[0374]

[0375] The synthesis of intermediate C-3 is similar to that of intermediate C-1, except that raw material B-1 is replaced by raw material B-3.

[0376] Synthesis of intermediate C-4:

[0377]

[0378] The synthesis of intermediate C-4 is similar to that of intermediate C-1, except that raw material B-4 is used instead of raw material B-1.

[0379] Synthesis of Compound 1:

[0380]

[0381]

[0382] Add raw material E-1 (20 mmol, 6.71 g) and cesium carbonate (55.2 mmol, 17.99 g) to a two-necked flask. Add 250 mL of anhydrous DMF under nitrogen protection and stir at room temperature for 65 minutes. Add raw material D-1 (20 mmol, 5.59 g) under nitrogen protection. Reflux the solution under magnetic stirring for 38 hours. Cool, filter, wash with water, dry, and pass through a column to obtain intermediate F-1.

[0383] Intermediate F-1 (10 mmol, 5.95 g) was dissolved in 120 mL of tetrahydrofuran (THF) solution. Under nitrogen purging at -78 °C, 4.7 mL of tert-butyllithium (2.5 M, 11.7 mmol) n-hexane solution was slowly added. After stirring at -78 °C for 6 hours, 30 mL of tetrahydrofuran solution of starting material G-1 (10 mmol, 1.80 g) was slowly added. The reaction mixture was then slowly heated to room temperature and stirred overnight. 30 mL of dilute hydrochloric acid (1.0 M), distilled water, and ethyl acetate were added to the reaction mixture. The aqueous layer was separated and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and filtered. After removing the solvent under reduced pressure, the crude product was dissolved in anhydrous dichloromethane, and then 47% boron trifluoride-diethyl ether was slowly added. The reaction mixture was stirred overnight and then slowly quenched with an aqueous 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 H-1.

[0384] Intermediate H-1 (5 mmol, 3.16 g), intermediate C-1 (5 mmol, 2.54 g), CuI catalyst (1 mmol, 0.19 g), and K3PO4 (25 mmol, 5.31 g) were added sequentially to a three-necked flask. Then, under a nitrogen atmosphere, trans-1,2-cyclohexanediamine (1.8 mmol, 0.21 g) and 90 mL of dioxane were added. The mixture was stirred at 106 °C for 24 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 I-1.

[0385] In a three-necked flask under nitrogen protection, intermediate I-1 (10 mmol, 10.58 g) and 140 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 68 °C and reacted for 7.5 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 8 h. Next, N,N-diisopropylethylamine (20 mmol, 3.5 mL) was added at 0 °C, the system was heated to 130 °C and reacted for 17 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 1. Compound 1 was reacted in toluene solution (1 × 10⁻⁶) -5 The half-width of the peak (M) was 22 nm, obtained by measuring the peak using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0386] Synthesis of compound 2:

[0387]

[0388] The synthesis of intermediate I-2 is similar to that of intermediate I-1, except that intermediate C-1 is replaced by intermediate C-2.

[0389] The synthesis of compound 2 is similar to that of compound 1, except that intermediate I-1 is replaced by intermediate I-2. Compound 2 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the peak (M) was 23 nm, obtained by measuring the peak using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0390] Synthesis of compound 17:

[0391]

[0392] The synthesis of intermediate H-3 is similar to that of intermediate H-1, except that raw material G-1 is replaced by raw material G-3.

[0393] The synthesis of intermediate I-3 is the same as that of intermediate I-1, except that intermediate H-1 is replaced by intermediate H-3 and intermediate C-1 is replaced by intermediate C-2.

[0394] The synthesis of compound 17 is similar to that of compound 1, except that intermediate I-1 is replaced by intermediate I-3. Compound 17 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the peak (M) was 23 nm, obtained by measuring the peak using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0395] Synthesis of compound 18:

[0396]

[0397] The synthesis of intermediate I-4 is the same as that of intermediate I-1, except that intermediate H-1 is replaced by intermediate H-3 and intermediate C-1 is replaced by intermediate C-3.

[0398] The synthesis of compound 18 is similar to that of compound 1, except that intermediate I-1 is replaced by intermediate I-4. Compound 18 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the peak (M) was 24 nm, obtained by measuring a Horiba Fluorolog-3 series fluorescence spectrometer.

[0399] Synthesis of compound 41:

[0400]

[0401]

[0402] The synthesis of intermediate F-5 is similar to that of intermediate F-1, except that raw material D-5 is used instead of raw material D-1.

[0403] The synthesis of intermediate H-5 is similar to that of intermediate H-1, except that intermediate F-1 is replaced by intermediate F-5.

[0404] The synthesis of intermediate I-5 is the same as that of intermediate I-1, except that intermediate H-1 is replaced by intermediate H-5 and intermediate C-1 is replaced by intermediate C-2.

[0405] The synthesis of compound 41 is similar to that of compound 1, except that intermediate I-1 is replaced by intermediate I-5. Compound 41 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the peak (M) was 23 nm, obtained by measuring the peak using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0406] Synthesis of compound 165:

[0407]

[0408]

[0409] The synthesis of intermediate F-6 is similar to that of intermediate F-1, except that raw material D-6 is used instead of raw material D-1.

[0410] The synthesis of intermediate H-6 is similar to that of intermediate H-1, except that intermediate F-1 is replaced by intermediate F-6.

[0411] The synthesis of intermediate I-6 is the same as that of intermediate I-1, except that intermediate H-1 is replaced by intermediate H-6 and intermediate C-1 is replaced by intermediate C-2.

[0412] The synthesis of compound 165 is similar to that of compound 1, except that intermediate I-1 is replaced by intermediate I-6. Compound 165 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the peak (M) was 25 nm, obtained by measuring the peak width using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0413] Synthesis of compound 181:

[0414]

[0415] The synthesis of intermediate H-7 is the same as that of intermediate H-1, except that intermediate F-1 is replaced by intermediate F-6 and raw material G-1 is replaced by raw material G-3.

[0416] The synthesis of intermediate I-7 is the same as that of intermediate I-1, except that intermediate H-1 is replaced by intermediate H-7 and intermediate C-1 is replaced by intermediate C-3.

[0417] The synthesis of compound 181 is similar to that of compound 1, except that intermediate I-1 is replaced by intermediate I-7. Compound 181 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the peak (M) was 25 nm, obtained by measuring the peak width using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0418] Synthesis of compound 356:

[0419]

[0420] The synthesis of intermediate I-8 is the same as that of intermediate I-1, except that intermediate H-1 is replaced by intermediate H-3 and intermediate C-1 is replaced by intermediate C-4.

[0421] The synthesis of compound 356 is similar to that of compound 1, except that intermediate I-1 is replaced by intermediate I-8. Compound 356 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the peak (M) was 23 nm, obtained by measuring the peak using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0422] Synthesis of compound 405:

[0423]

[0424]

[0425] The synthesis of intermediate F-9 is similar to that of intermediate F-1, except that raw material D-9 is used to replace raw material D-1, and raw material E-9 is used to replace raw material E-1.

[0426] Synthesis of intermediate H-9: Under a N2 atmosphere at 0 °C, 20 mL (1.6 M) of a hexane solution of n-butyllithium was added dropwise with stirring to 50 mL of an anhydrous diethyl ether solution of intermediate F-9 (4.39 g, 7 mmol); the mixture was stirred at 0 °C for 1.5 h, and then 20 mL of an anhydrous toluene solution of starting material G-9 (2.01 g, 8 mmol) was added dropwise; the reaction mixture was stirred at 35 °C for 5 h, and then cooled to room temperature; after adding water, the product was extracted with ethyl acetate. The combined organic layers were washed with brine and dried over anhydrous Na2SO4; after filtration and evaporation, the residue was passed through a column to obtain intermediate H-9.

[0427] The synthesis of intermediate I-9 is similar to that of intermediate I-1, except that intermediate H-1 is replaced by intermediate H-9 and intermediate C-1 is replaced by intermediate C-2.

[0428] The synthesis of compound 405 is similar to that of compound 1, except that intermediate I-1 is replaced by intermediate I-9. Compound 405 is synthesized in toluene solution (1×10⁻⁶). -5 The half-width of the peak (M) was 23 nm, obtained by measuring the peak using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0429] The structural characterization of the compounds obtained in each embodiment is shown in Table 1:

[0430] Table 1

[0431]

[0432] The following describes in detail the application effects of the organic electroluminescent materials synthesized in this invention in devices through device examples 1-9 and device comparative examples 1-2. The fabrication processes of device examples 2-9 and device comparative examples 1-2 are completely identical to those of device example 1, and the same substrate and electrode materials are used. The film thickness of the electrode materials is also kept consistent. The only difference is that the light-emitting layer material in the device is replaced. The layer structures and test results of each device example are shown in Tables 2-1 and 3, respectively.

[0433] Device Example 1

[0434] like Figure 1As shown, the transparent substrate layer 1 is transparent glass. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), 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, HT-1 and HI-1 with a thickness of 10nm are deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 60nm thick layer of HT-1 is deposited as a hole transport layer 4. Subsequently, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the organic electroluminescent device is fabricated, using GH-1 and GH-2 as the host materials and compound 1 as the dopant material, with a mass ratio of GH-1, GH-2, and compound 1 of 69:30:1. The light-emitting layer film thickness is 30nm. Following the aforementioned light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer serves as the hole-blocking layer 7. Following the hole-blocking layer 7, ET-1 and Liq are vacuum-deposited at a mass ratio of 1:1, resulting in a film thickness of 30 nm; this layer serves as 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 serves as the electron injection layer 9. On the electron injection layer 9, an 80 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9; this layer serves as the cathode layer 10.

[0435] The application effects of the organic electroluminescent materials synthesized in this invention in devices are described in detail below through device examples 10-61 and device comparative examples 3-4. The fabrication processes of device examples 11-61 and device comparative examples 3-4 are exactly the same as those of device example 10, and the same substrate and electrode materials are used. The film thickness of the electrode materials is also kept consistent. The only difference is that the light-emitting layer material in the device is replaced. The layer structure and test results of each device example are shown in Tables 2-2 and 3, respectively.

[0436] Device Example 10

[0437] 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 is used as the first dopant, and compound 1 is used as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and compound 1 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.

[0438] The molecular structural formulas of the relevant materials are shown below:

[0439]

[0440] HI-1 HT-1 EB-1 Liq

[0441]

[0442] ET-1 HB-1 GH-1

[0443]

[0444] GH-2 GD-1 ref-1 ref-2

[0445] After completing the organic electroluminescent device as described above, the anode and cathode are connected using a known driving circuit, and the current efficiency and lifetime of the device are measured. Examples and comparisons of devices prepared using the same method are shown in Tables 2-1 and 2-2; the test results for the current efficiency and lifetime of the obtained devices are shown in Table 3.

[0446] Table 2-1

[0447]

[0448] Table 2-2

[0449]

[0450]

[0451]

[0452]

[0453]

[0454] Table 3

[0455]

[0456] Note: Current efficiency and peak emission were measured using an IVL (current-voltage-luminance) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.). Both current efficiency and peak emission data are within 10 mA / cm². 2 The following test was conducted. The lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan. LT95 refers to the time it takes for the device brightness to decay to 95%, and the lifetime data is in the range of 35 mA / cm². 2 The results were obtained from the following tests.

[0457] As can be seen from the device data results in Table 3, compared with the comparative compounds ref-1 and ref-2, the compound of the present invention can achieve the green light emission effect very well and has higher current efficiency; compared with the devices of comparative examples 1-4, the current efficiency and lifetime of the device are significantly improved compared with the devices of known materials.

[0458] 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): General formula (1) In general formula (1), the occurrence of the same or different M1, M2, M3, M4, and M5 is represented by C6~C. 30 Aryl or C2~C 30 Mixed aromatics; X1 and X2 can be represented independently as either carbon atoms or silicon atoms; R1, R2, R3, R4, R5, R6, R7, R8, and R9 are each independently represented as a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, or a C1-C group substituted or unsubstituted with a substituent. 10 Alkyl groups, substituted or unsubstituted C3~C 10 Cycloalkyl, C2-C substituted or unsubstituted 10 Alkenyl, C2~C with or without substituents 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 heteroaryl groups, C2-C substituted or unsubstituted groups 30 Boronyl groups, substituted or unsubstituted C3~C 30 One of the silane groups; The connection methods of R1, R2, R3, R4, R5, R6, R7, and R8 are either single-key connection or parallel ring connection; a1, a2, a3, a4, and a5 are each independently represented as 0 to the maximum allowed number of substitutions; a6 and a8 can be independently represented as 0, 1, 2, 3 or 4; a7 represents 0, 1, or 2; Ar1 and Ar2 are independently represented as C3~C3 cells substituted with or unsubstituted with R. 10 Cycloalkyl, C6~C substituted or unsubstituted 30 Aryl group, C3~C group substituted or unsubstituted with R 30 Silyl, C2~C substituted or unsubstituted 30 One of the heteroaryl groups; R represents a deuterium atom, a halogen atom, a cyano group, or a C1-C group that is substituted or unsubstituted. 10 Alkyl groups, substituted or unsubstituted C3~C 10 Cycloalkyl, C2-C substituted or unsubstituted 10 Alkenyl, C2~C with or without substituents 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 Heteroaryl groups, C2-C groups substituted or unsubstituted 30 Boronyl groups, substituted or unsubstituted C3~C 30 One of the silane groups; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1~C1 groups. 10 Alkyl or deuterated 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, C1~C 10 Alkyl-substituted C6~C 30 Aryl, C2~C 30 heteroaryl, C3~C 30 Silyl, deuterium-substituted C2~C 30 Any one or more combinations of heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

2. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The structure of the boron-containing resonance organic compound is shown in any one of general formulas (2-1) to (2-3): General formula (2-1) General formula (2-2) General formula (2-3) In general formulas (2-1) to (2-3), the definitions of M2, M3, M5, R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar1, Ar2, X1, X2, a6, a7, and a8 are the same as those in general formula (1); a1 and a2 can be independently represented as 0, 1, 2 or 3; a3, a4, and a5 can be independently represented as 0, 1, 2, 3, or 4.

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 (3-1) to (3-13): General formula (3-1) General formula (3-2) General formula (3-3) General formula (3-4) General formula (3-5) General formula (3-6) General formula (3-7) General formula (3-8) General formula (3-9) General formula (3-10) General formula (3-11) General formula (3-12) General formula (3-13) In general formulas (3-1) to (3-13), the definitions of R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar1, Ar2, X1, X2, a6, a7, and a8 are the same as those in general formula (1); a1 and a2 can be independently represented as 0, 1, 2 or 3; a3, a4, a5, a 10 a 11 a 12 Each can be independently represented as 0, 1, 2, 3, or 4; a'2, a'3, a'5 represent 0, 1, 2, 3, 4, or 5; a 13 Represented as 0, 1, or 2; X3, X4, and X5 can be independently represented as oxygen atoms, sulfur atoms, or N(R0); Each occurrence of R0 is independently represented as C1~C1. 10 Alkyl or deuterated 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, C1~C 10 Alkyl-substituted C6~C 30 Aryl, C2~C 30 C2~C of heteroaryl and deuterium-substituted compounds 30 One of the heteroaryl groups; R 10 R 11 R 12 R 13 Each occurrence is represented independently as a hydrogen atom, deuterium atom, halogen atom, cyano group, or C1~C with or without substituents. 10 Alkyl groups, substituted or unsubstituted C3~C 10 Cycloalkyl, C2-C substituted or unsubstituted 10 Alkenyl, C2~C with or without substituents 10 Alkyne group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 heteroaryl groups, C2-C substituted or unsubstituted groups 30 Boronyl groups, substituted or unsubstituted C3~C 30 One of the silane groups; The substituents are selected from deuterium atoms, halogen atoms, cyano groups, C1~C1 groups. 10 Alkyl or deuterated 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, C1~C 10 Alkyl-substituted C6~C 30 Aryl, C2~C 30 heteroaryl, C3~C 30 Silyl, deuterium-substituted C2~C 30 Any one or more combinations of heteroaryl groups; The heteroatom in the heteroaryl group is selected from one or more of O, S, N, Si, and B.

4. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The structure of the boron-containing resonance organic compound is shown in any one of general formulas (4-1) to (4-2): General formula (4-1) General formula (4-2) In general formulas (4-1) to (4-2), the definitions of R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar1, Ar2, X1, X2, a6, a7, and a8 are the same as those in general formula (1); a3, a4, and a5 can be independently represented as 0, 1, 2, 3, or 4; a'2 represents 0, 1, 2, 3, 4, or 5.

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 (5-1) to (5-2): General formula (5-1) General formula (5-2) In general formulas (5-1) to (5-2), the definitions of R1, R2, R3, R4, R5, R6, R7, R8, R9, Ar1, Ar2, X1, X2, a6, a7, and a8 are the same as those in general formula (1); a5 can be independently represented as 0, 1, 2, 3 or 4; a'2 represents 0, 1, 2, 3, 4, or 5.

6. The boron-containing resonance-type organic compound according to any one of claims 1-5, characterized in that, The R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 R 11 R 12 R 13 Each of these can be independently represented as a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group (substituted or unsubstituted), a methyl group (substituted or unsubstituted), an ethyl group (substituted or unsubstituted), an isopropyl group (substituted or unsubstituted), a tert-butyl group (substituted or unsubstituted), a tert-pentyl group (substituted or unsubstituted), a cyclopentyl group (substituted or unsubstituted), a cyclohexyl group (substituted or unsubstituted), a phenyl group (substituted or unsubstituted), or a dialkyl group (substituted or unsubstituted). Biphenyl, terphenyl (substituted or unsubstituted), diphenyl ether (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthraceneyl (substituted or unsubstituted), phenanthryl (substituted or unsubstituted), pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), furanyl (substituted or unsubstituted), thiopheneyl (substituted or unsubstituted), benzofuranyl (substituted or unsubstituted), dibenzofuranyl (substituted or unsubstituted) alkyl, dibenzothiophene group (substituted or unsubstituted), carbazolyl group (substituted or unsubstituted), N-phenylcarbazolyl group (substituted or unsubstituted), 9,9-dimethylfluorenyl group (substituted or unsubstituted), diphenylfluorenyl group (substituted or unsubstituted), spirofluorenyl group (substituted or unsubstituted), xanthone group (substituted or unsubstituted), triazine group (substituted or unsubstituted), methoxy group (substituted or unsubstituted), tert-butoxy group (substituted or unsubstituted). One of the following: diphenylamino group substituted or unsubstituted; 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group substituted or unsubstituted; indole group substituted or unsubstituted; benzoindole group substituted or unsubstituted; N-phenyl-1-naphthylamino group substituted or unsubstituted; N-phenyl-2-naphthylamino group substituted or unsubstituted; trimethylsilyl group substituted or unsubstituted; and tert-butyldimethylsilyl group substituted or unsubstituted. Ar1 and Ar2 represent methyl (substituted or unsubstituted), ethyl (substituted or unsubstituted), isopropyl (substituted or unsubstituted), tert-butyl (substituted or unsubstituted), tert-pentyl (substituted or unsubstituted), cyclopentyl (substituted or unsubstituted), cyclohexyl (substituted or unsubstituted), phenyl (substituted or unsubstituted), diphenyl (substituted or unsubstituted), terphenyl (substituted or unsubstituted), naphthyl (substituted or unsubstituted), anthracene (substituted or unsubstituted), phenanthryl (substituted or unsubstituted), pyridyl (substituted or unsubstituted), quinolinyl (substituted or unsubstituted), and furfural (substituted or unsubstituted). One of the following: yl, thiophene group (substituted or unsubstituted), benzofuran 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), spirofluorenyl group (substituted or unsubstituted), xanthone group (substituted or unsubstituted), triazine group (substituted or unsubstituted), 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group (substituted or unsubstituted), indole group (substituted or unsubstituted), and benzoindole group (substituted or unsubstituted). The R represents a deuterium atom, a halogen atom, a cyano group, an adamantyl group (substituted or unsubstituted), a methyl group (substituted or unsubstituted), an ethyl group (substituted or unsubstituted), an isopropyl group (substituted or unsubstituted), a tert-butyl group (substituted or unsubstituted), a tert-pentyl group (substituted or unsubstituted), a cyclopentyl group (substituted or unsubstituted), a cyclohexyl group (substituted or unsubstituted), a phenyl group (substituted or unsubstituted), a diphenyl group (substituted or unsubstituted), or a group composed of... Substituted or unsubstituted triphenyl, substituted or unsubstituted diphenyl ether, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted benzofuranyl, substituted or unsubstituted dibenzofuranyl. 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 diphenylfluorenyl group, substituted or unsubstituted spirofluorenyl group, substituted or unsubstituted xanthone group, substituted or unsubstituted triazine group, substituted or unsubstituted methoxy group, substituted or unsubstituted tert-butoxy group, substituted or unsubstituted One of the following: diphenylamino group substituted or unsubstituted; 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl group substituted or unsubstituted; indole group substituted or unsubstituted; benzoindole group substituted or unsubstituted; N-phenyl-1-naphthylamino group substituted or unsubstituted; N-phenyl-2-naphthylamino group substituted or unsubstituted; trimethylsilyl group substituted or unsubstituted; and tert-butyldimethylsilyl group substituted or unsubstituted. The R0 represents one of the following: adamantyl, methyl, ethyl, isopropyl, tert-butyl, tert-pentyl, cyclopentyl, cyclohexyl, phenyl, diphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, diphenylfluorenyl, spirofluorenyl, xanthonel, triazine, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, indolyl, benzoindolyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, and tert-butyl-substituted diphenyl. M1, M2, M3, M4, and M5 represent one of the following: phenyl, diphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, indoleyl, and benzoindoleyl. The substituents used for the substituent groups are selected from deuterium, chlorine, fluorine, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-amyl, tert-butyl, butyl, phenyl, diphenyl, naphthyl, anthracene, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiophene, indoleyl, pyrroleyl, and dibenzofuranyl. Dibenzothiophene, 9,9-dimethylfluorenyl, spirofluorenyl, carbazolyl, N-phenylcarbazolyl, carbazolinyl, azirphenanthrenel, diphenylamino, 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, benzoindolyl, deuterated adamantyl, deuterated methyl, deuterated ethyl, deuterated propyl, deuterated isopropyl, deuterated tert-amyl, deuterated tert-butyl, deuterated... Butyl, deuterated phenyl, deuterated diphenyl, deuterated naphthyl, deuterated anthracene, deuterated phenanthryl, deuterated pyridyl, deuterated pyrimidinyl, deuterated pyrazinyl, deuterated pyridazinyl, deuterated benzoxazolyl, deuterated benzothiazolyl, deuterated quinoxalinyl, deuterated quinolinyl, deuterated isoquinolinyl, deuterated furanyl, deuterated thiopheneyl, deuterated indole One or more of the following: dolomyl, deuterated pyrroleyl, deuterated dibenzofuranyl, deuterated dibenzothiopheneyl, deuterated 9,9-dimethylfluorenyl, deuterated spirofluorenyl, deuterated carbazolyl, deuterated N-phenylcarbazolyl, deuterated carbazolinyl, deuterated azirophenonel, deuterated 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthyl, and deuterated benzoindolyl.

7. The boron-containing resonance-type organic compound according to claim 1, characterized in that: The specific structural formula of the boron-containing resonance-type organic compound is any one of the following structures: (1) (2) (3) (4) (5) (6) (7) (8) (9) (10) (11) (12) (13) (14) (15) (16) (17) (18) (19) (20) (21) (22) (23) (24) (25) (26) (27) (28) (29) (30) (31) (32) (33) (34) (35) (36) (37) (38) (39) (40) (41) (42) (43) (44) (45) (46) (47) (48) (49) (50) (51) (52) (53) (54) (55) (56) (57) (58) (59) (60) (61) (62) (63) (64) (65) (66) (67) (68) (69) (70) (71) (72) (73) (74) (75) (76) (77) (78) (79) (80) (81) (82) (83) (84) (85) (86) (87) (88) (89) (90) (91) (92) (93) (94) (95) (96) (97) (98) (99) (100) (101) (102) (103) (104) (105) (106) (107) (108) (109) (110) (111) (112) (113) (114) (115) (116) (117) (118) (119) (120) (121) (122) (123) (124) (125) (126) (127) (128) (129) (130) (131) (132) (133) (134) (135) (136) (137) (138) (139) (140) (141) (142) (143) (144) (145) (146) (147) (148) (149) (150) (151) (152) (153) (154) (155) (156) (157) (158) (159) (160) (161) (162) (163) (164) (165) (166) (167) (168) (169) (170) (171) (172) (173) (174) (175) (176) (177) (178) (179) (180) (181) (182) (183) (184) (185) (186) (187) (188) (189) (190) (191) (192) (193) (194) (195) (196) (197) (198) (199) (200) (201) (202) (203) (204) (205) (206) (207) (208) (209) (210) (211) (212) (213) (214) (215) (216) (217) (218) (219) (220) (221) (222) (223) (224) (225) (226) (227) (228) (229) (230) (231) (232) (233) (234) (235) (236) (237) (238) (239) (240) (241) (242) (243) (244) (245) (246) (247) (248) (249) (250) (251) (252) (253) (254) (255) (256) (257) (258) (259) (260) (261) (262) (263) (264) (265) (266) (267) (268) (269) (270) (271) (272) (273) (274) (275) (276) (277) (278) (279) (280) (281) (282) (283) (284) (285) (286) (287) (288) (289) (290) (291) (292) (293) (294) (295) (296) (297) (298) (299) (300) (301) (302) (303) (304) (305) (306) (307) (308) (309) (310) (311) (312) (313) (314) (315) (316) (317) (318) (319) (320) (321) (322) (323) (324) (325) (326) (327) (328) (329) (330) (331) (332) (333) (334) (335) (336) (337) (338) (339) (340) (341) (342) (343) (344) (345) (346) (347) (348) (349) (350) (351) (352) (353) (354) (355) (356) (357) (358) (359) (360) (361) (362) (363) (364) (365) (366) (367) (368) (369) (370) (371) (372) (373) (374) (375) (376) (377) (378) (379) (380) (381) (382) (383) (384) (385) (386) (387) (388) (389) (390) (391) (392) (393) (394) (395) (396) (397) (398) (399) (400) (401) (402) (403) (404) (405) (406) (407) (408) (409) (410) (411) (412) (413) (414) (415) (416) (417) (418) (419) (420) (421) (422) (423) (424) (425) (426) (427) (428) (429) (430) (431) (432) (433) (434) (435) (436) (437) (438) (439) (440) (441) (442) (443) (444) (445) (446) (447) (448) (449) (450) (451) (452) (453) (454) (455) (456) (457) (458)。 8. An organic light-emitting device, comprising a substrate, a first electrode, an organic functional material layer, and a second electrode, wherein the first electrode is located on the substrate, the organic functional material layer is located on the first electrode, and the second electrode is located on the functional layer, characterized in that: The organic functional material layer contains the boron-containing resonant organic compound as described in any one of claims 1-7; Preferably, the organic functional material layer includes a light-emitting layer, characterized in that: the light-emitting layer includes a host material and a dopant material, wherein the dopant material is a boron-containing resonant organic compound as described in any one of claims 1-7.

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

10. The organic light-emitting device according to claim 8, wherein the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material, characterized in that: The exciton sensitizing material is a complex containing a metal element, and the doping material is a boron-containing resonance organic compound as described in any one of claims 1-7.

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