An organic electroluminescent device comprising a boron-containing organic compound and a preparation method thereof

Abstract

The application discloses a kind of boron-containing organic compounds and the preparation of organic electroluminescent device, belong to semiconductor technical field.The structure of the organic compound of the present application is as shown in any one of general formula (1) to general formula (4), the compound of the present application has narrow half-width, suitable light color, can be used as the green light doping material of the light-emitting layer of organic electroluminescent device, so as to improve the light color purity and life of device.

Description

[0001] This application is a divisional application of prior application number 202211132401.3, filed on September 13, 2022, entitled "A Boron-Containing Organic Compound and an Organic Electroluminescent Device Prepared Therefrom". Technical Field

[0002] This invention relates to the field of semiconductor technology, and more particularly to a boron-containing organic compound and an organic electroluminescent device prepared therefrom. Background Technology

[0003] Traditional fluorescent doped materials, limited by early technologies, can only emit light using 25% of singlet excitons generated by electrical excitation. The internal quantum efficiency of these devices is low, and the external quantum efficiency is generally below 5%, significantly lower than that of phosphorescent devices. Phosphorescent materials, due to the strong spin-orbit coupling at the heavy atom centers enhancing intersystem crossing, can effectively utilize singlet and triplet excitons generated by electrical excitation for emission. However, most phosphorescent materials are expensive, have poor material stability, poor color purity, and suffer from severe efficiency roll-off, limiting their application in OLEDs.

[0004] With the advent of the 5G era, higher requirements have been placed on color rendering standards. In addition to high efficiency and stability, luminescent materials also need narrower half-widths (HWHMs) to improve the purity of the emitted color in devices. Fluorescent dopants can achieve high fluorescence quantum density and narrow HWHM through molecular engineering. Significant breakthroughs have been achieved in blue fluorescent dopants, with the HWHM of boron-based materials reduced to below 30 nm. However, research on the green light region, which is more sensitive to the human eye, has mainly focused on phosphorescent dopants. However, the peak shape of these dopants is difficult to narrow using simple methods. Therefore, researching efficient green fluorescent dopants with narrow HWHMs is of great significance in meeting higher color rendering standards.

[0005] In addition, sensitization technology combines triplet exciton sensitizing 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, achieving 100% in-device quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization in fluorescent doping materials and effectively leverage the high fluorescence quantum yield, high device stability, high color purity, and low cost of fluorescent doping materials, showing broad prospects in OLED applications.

[0006] Boron compounds with resonant structures are more likely to achieve narrow half-width emission (HWHM). When applied to sensitization techniques, these materials can enable the fabrication of devices with high efficiency and narrow HWHM emission. For example, CN 107507921 A and CN 110492006 A disclose a light-emitting layer combination technique 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 achieve efficiencies comparable to phosphorescence and relatively narrow HWHM. Therefore, developing sensitization techniques 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

[0007] To address the aforementioned problems in the prior art, this invention provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom. The compound of this invention possesses a specific boron-nitrogen fused ring structure, resulting in a narrow full width at half maximum (FWHM), making it suitable as a green dopant material for the emitting layer of an organic electroluminescent device, thereby improving the purity and lifetime of the emitted light.

[0008] The technical solution of the present invention is as follows: a boron-containing organic compound, wherein the structure of the boron-containing organic compound is shown in any one of general formulas (1) to (4):

[0009]

[0010]

[0011] In general formulas (1) to (4), M1 to M8 are independently represented as substituted or unsubstituted C6-C6. 30 aryl or C2-C 30 heteroaryl groups;

[0012] Z is represented as C-R1;

[0013] X is represented as N-R2, O, S, C(R3)(R4), where R3 and R4 can be directly connected to form a ring;

[0014] Ar1-Ar8 are independently represented as substituted or unsubstituted C6-C. 30 aryl or C2-C 30 The heteroaryl groups, and Ar1 can be linked with Ar2, Ar3 with Ar4, Ar5 with Ar6, and Ar7 with Ar8 to form a ring;

[0015] The recurrence of R1, R3, and R4, whether identical or different, represents hydrogen atoms, deuterium atoms, halogen atoms, and substituted or unsubstituted C1-C1 atoms.10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0016] Each occurrence of the same or different R2 indicates substituted or unsubstituted C1-C2. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0017] The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C5-C 10 Cycloalkenyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups;

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

[0019] In a preferred embodiment, the structure of the organic compound is shown in any one of general formulas (5) to (8):

[0020]

[0021] In general formulas (5) to (8), the meanings of Z, Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are the same as those defined above;

[0022] Z1 is represented as CR a Z2 is represented as CR b Z3 is represented as CR c Z4 is represented as CR d Z5 is represented as CR e ;

[0023] R a R b R c R d R eEach instance of the same or different element is represented by a hydrogen atom, deuterium atom, halogen atom, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0024] The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C5-C 10 Cycloalkenyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups;

[0025] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0026] In a preferred embodiment, the structure of the organic compound is shown in any one of general formulas (9) to (40):

[0027]

[0028]

[0029]

[0030] In general formulas (9) to (40), the meaning of Z is the same as the limitation mentioned above.

[0031] In a preferred embodiment, the structure of the organic compound is shown in any one of general formulas (41) to (76):

[0032]

[0033]

[0034]

[0035] In general formulas (41) to (76), the meaning of Z is the same as the limitation mentioned above.

[0036] In a preferred embodiment, the structure of the organic compound is shown in any one of general formulas (77) to (80):

[0037]

[0038] In general formulas (77) to (80), the meanings of M1-M8, Z, Z1, Z2, Z3, Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, Ar7, and Ar8 are the same as those defined above.

[0039] In a preferred embodiment, the structure of the organic compound is shown in any one of general formulas (81) to (86):

[0040]

[0041] In general formulas (81) to (86), the meanings of M1-M8, Z, Z1, Z2, Z3, Z4, and Z5 are the same as those defined above.

[0042] In a preferred embodiment, the structure of the organic compound is shown in any one of general formulas (87) to (93):

[0043]

[0044] In formulas (87) to general formula (93), the meanings of Z, Z1, Z2, Z3, Z4, and Z5 are the same as those defined above;

[0045] Z6 is represented as CR f Z7 is represented as CR g ;

[0046] R f R g Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, halogen atom, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C1-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0047] The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C5-C 10 Cycloalkenyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups;

[0048] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0049] In the preferred embodiment, R1, R3, R4, Ra, R b R c R d R e R f R g Each of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazole, N-phenylcarbazole, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl The following are substituted phenyl groups: methyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boronyl, methoxy, and tert-butoxy.

[0050] R2 represents adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl One of the following: substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, and phenyl-substituted triazineyl;

[0051] The Ar1-Ar8 are represented as phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, and methyl-substituted diphenyl. One of the following: methyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, and phenyl-substituted triazineyl;

[0052] The M1-M8 rings represent benzene rings, naphthyl rings, anthracene rings, phenanthrene rings, pyridine rings, quinoline rings, furan rings, thiophene rings, benzofuran rings, benzothiophene rings, dibenzofuran rings, dibenzothiophene rings, carbazole rings, N-phenylcarbazole rings, 9,9-dimethylfluorene rings, and spirofluorene rings.

[0053] The substituents used for the substituent groups are selected from one of the following: deuterium atom, halogen atom, adamantyl, methyl, trifluoromethyl, ethyl, isopropyl, tert-butyl, cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, fluorine-substituted phenyl, methyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, phenyl-substituted amino, tert-butylphenyl-substituted amino, and phenyl-substituted triazineyl.

[0054] In the preferred embodiment, R1, R3, R4, Ra, R b R c R d R e R f R g It can be represented as the structure shown below:

[0055]

[0056]

[0057] M1-M8 can be represented by any of the following ring structures:

[0058]

[0059] The definition of Z is the same as the limitation mentioned above.

[0060] In a preferred embodiment, the organic compound has any one of the following structures:

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078]

[0079] An organic electroluminescent device includes a cathode and an anode, and an organic light-emitting functional layer therebetween, the organic light-emitting functional layer including a light-emitting layer containing the boron-containing organic compound.

[0080] In a preferred embodiment, the light-emitting layer comprises a host material and a dopant material, wherein the dopant material contains the aforementioned boron-containing organic compound.

[0081] In a preferred embodiment, 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 organic compound.

[0082] In a preferred embodiment, the light-emitting layer comprises a host material, an exciton-sensitizing material, and a dopant material, wherein the exciton-sensitizing material is a complex containing a metal element, and the dopant material is the boron-containing organic compound.

[0083] The beneficial technical effects of this invention are as follows:

[0084] (1) The compound of the present invention can be used as a dopant material for OLED devices, and can emit green fluorescence under the action of an electric field. It can be applied to OLED lighting or OLED display fields.

[0085] (2) The compound of the present invention is used as a doping material, and TADF sensitizer is introduced as a second host, which can effectively improve device efficiency;

[0086] (3) The compounds of the present invention have a narrower FWHM spectrum, which can effectively improve the color gamut of the device and improve the luminous efficiency of the device;

[0087] (4) The compounds of the present invention can achieve green light emission relatively easily;

[0088] (5) The specific boron-nitrogen fused ring structure of the compound of the present invention can expand the molecular spatial volume, reduce the intermolecular interaction force, improve the device sensitization efficiency and reduce the device roll-off. Attached Figure Description

[0089] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in this invention are applied;

[0090] 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

[0091] The technical solutions of the embodiments of the present invention will be clearly and completely described below with reference to the accompanying drawings. Unless otherwise specified, the embodiments and features in the embodiments of the present invention can be combined with each other. The present invention will be further described below with reference to the accompanying drawings and specific embodiments, but this is not intended to limit the present invention.

[0092] 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.

[0093] In this invention, C6-C is substituted or unsubstituted. 30 aryl and / or substituted or unsubstituted C2-C 30 Heteroaryl refers to substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinone, substituted or unsubstituted phenanthrene, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrene, substituted or unsubstituted biphenyl, substituted or unsubstituted para-triphenyl, substituted or unsubstituted meta-triphenyl, and substituted or unsubstituted phenyl groups. Substituted or unsubstituted triphenyl, substituted or unsubstituted perylene, substituted or unsubstituted indole, substituted or unsubstituted furanyl, substituted or unsubstituted thiophene, substituted or unsubstituted pyrrole, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazine, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophene, substituted or Unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted naphridyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fumonyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl, combinations thereof, or fused rings of the foregoing groups, but not limited thereto.

[0094] The C1-C of this invention 10 Alkyl groups (including straight-chain alkyl and branched-chain alkyl) refer to methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, etc., but are not limited to these.

[0095] The halogen atom mentioned in this invention refers to chlorine atom, fluorine atom or bromine atom, etc., but is not limited to these.

[0096] The C3-C of this invention 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group comprising 3 to 10 carbon atoms as cyclic atoms. In this document, C4-C9 cycloalkyl groups are preferred, C5-C8 cycloalkyl groups are more preferred, and C5-C7 cycloalkyl groups are particularly preferred. Non-limiting examples may include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

[0097] 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 plastic substrates; and opaque substrates, such as silicon substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Depending on the properties of the substrate, its application direction varies. In this invention, a transparent PI film substrate is preferred. There are no particular limitations on the thickness of the substrate.

[0098] A first electrode is formed on a substrate, and the first electrode and a second electrode may be opposite each other. The first electrode may be an anode. The first electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it may be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). When the first electrode is a semi-transmissive electrode or a reflective electrode, it may include Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, or a mixture of metals. 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.

[0099] 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.

[0100] In this paper, the hole transport region constituting an organic electroluminescent device can be listed as a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0101] 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 OLED devices.

[0102] Examples of the aforementioned materials include phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinium derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinone derivatives, styrene-based anthracene derivatives, styrene-based amine derivatives, styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyaryl alkane derivatives, polyphenylene oxide and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and other conductive polymers, aromatic tertiary amine compounds, and styrene aminations. Compounds, triamines, tetraamines, benzidines, propyne diamine derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1,1'-bis(4-diarylaminophenyl)cyclohexane, 4,4'-bis(diarylamine)biphenyls, bis[4-(diarylamino)phenyl]methanes, 4,4'-bis(diarylamino)terphenyls, 4,4'-bis(diarylamino)tetraphenyls, 4,4'-bis(diarylamino)diphenyl ethers, 4,4'-bis(diarylamino)diphenylsulfanes, bis[4-(diarylamino)phenyl]dimethylmethanes, bis[4-(diarylamino)phenyl]-bis(trifluoromethyl)methanes, or 2,2-diphenylethylene compounds, etc.

[0103] Furthermore, depending on the device configuration requirements, the hole transport film layer between the electron blocking and hole injection layers of an organic electroluminescent device can be a single film layer or a stacked structure of multiple hole transport materials. In this paper, the film thickness of the various hole carrier conduction films with different functions is not particularly limited.

[0104] The hole injection layer comprises a host organic material capable of conducting holes, and a p-type doped material with a deep HOMO level (correspondingly, a deep LUMO level). Based on empirical observations, to achieve smooth hole injection from the anode to the organic film, the HOMO level of the host organic material used in the anode interface buffer layer must possess certain characteristics with the p-doped material. This is necessary to enable charge transfer states between the host and doped materials, achieve ohmic contact between the buffer layer and the anode, and realize efficient hole injection conduction from the electrode to the hole injection layer.

[0105] Based on the above empirical summary, different P-doped materials need to be selected to match the hole-based host materials of different HOMO energy levels in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0106] Therefore, in one embodiment of the present invention, in order to improve hole injection, the hole injection layer further comprises a p-type dopant material selected from the following charge-conducting materials: quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ); or hexaazatriphenyl derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenyl (HAT-CN); or cyclopropane derivatives, such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0107] 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 meter.

[0108] 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.

[0109] 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.

[0110] 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.

[0111] 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.

[0112] 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 organic compound represented by the general formula (1) of this invention.

[0113] The light-emitting layer can contain a single-substrate material or a dual-substrate material;

[0114] 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;

[0115] TADF materials refer to materials with thermally activated delayed fluorescence properties. They are characterized by a small energy difference between the first excited singlet and triplet states, allowing for the simultaneous utilization of both singlet and triplet excitons generated within the device, thus enabling the exciton utilization rate of electrogenerated excitons within the device to approach 100%. Compared to traditional fluorescent materials, TADF materials exhibit higher exciton utilization.

[0116] The light-emitting layer may include a host material, an exciton-sensitizing material, and a dopant material;

[0117] 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 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.

[0118] 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.

[0119] 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.

[0120] 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.

[0121] 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 efficiency. The hole-blocking layer of this invention can be disposed above the light-emitting layer. As the hole-blocking layer material for the organic electroluminescent device of this invention, compounds with hole-blocking properties known in the prior art can be used, such as phenanthroline derivatives like copper hydroxide (BCP), metal complexes of hydroxyquinoline derivatives like aluminum(III)bis(2-methyl-8-quinoline)-4-phenylphenol (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, pyrimidine derivatives like 9,9'-(5-(6-([1,1'-biphenyl]-4-yl)-2-phenylpyrimidin-4-yl)-1,3-phenylene)bis(9H-carbazole), etc. The thickness of the hole-blocking layer of this invention can be 2-200 nm, preferably 5-150 nm, but the thickness is not limited to this range.

[0122] 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 the received electrons to the light-emitting layer. Materials with high electron mobility are preferred. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials known in the prior art for organic electroluminescent devices can be used, such as metal complexes of hydroxyquinoline derivatives represented by Alq3, BAlq and Liq, various rare earth metal complexes, triazole derivatives, triazine derivatives such as 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthyl-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6), imidazole derivatives such as 2-(4-(9,10-bis(naphthyl-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201), oxadiazole derivatives, thiadiazole derivatives, carbodiimide derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, etc. 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.

[0123] An electron injection layer may be disposed above the electron transport layer. The electron injection layer material is typically preferably a material with a low work function, allowing electrons to be easily injected into the organic functional material layer. As the electron injection layer material for the organic electroluminescent device of the present invention, electron injection layer materials known in the art for organic electroluminescent devices can be used, such as lithium; lithium salts, such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate, or lithium azide; or cesium salts, such as cesium fluoride, cesium carbonate, or cesium azide. The thickness of the electron injection layer of the present invention may 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.

[0124] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmission electrode, a semi-transmission electrode, or a reflection electrode. When the second electrode is a transmission electrode, it may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, Ba, Ag, or compounds or mixtures thereof; when the second electrode is a semi-transmission electrode or a reflection electrode, it may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or compounds or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0125] 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.

[0126] 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, an organic film 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.

[0127] 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;

[0128] Example 1: Synthesis of Compound 6:

[0129]

[0130] 1. Under nitrogen protection, 10 mmol of starting material A-1, 10 mmol of starting material B-1, 12 mL of cesium carbonate, and 20 mL of anhydrous tetrahydrofuran were added to a three-necked flask, and the reaction was carried out at 120°C for 18 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-1. LC-MS: Measured value: 379.23 ([M+H)) + ).

[0131] 2. Under nitrogen protection, 10 mmol of starting material C-1, 10 mmol of starting material D-1, 12 mL of cesium carbonate, and 20 mL of anhydrous tetrahydrofuran were added to a three-necked flask, and the reaction was carried out at 140°C for 24 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-1. LC-MS: Measured value: 467.22 ([M+H) + ).

[0132] 3. Under nitrogen protection, 10 mmol of intermediate b-1, 10 mmol of starting material E-1, and 15 ml of trifluoroacetic acid solution were added to a three-necked flask, and the reaction was carried out at low temperature for 2 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-1. LC-MS: Measured value: 551.39 ([M+H)) + ).

[0133] 4. Add 10 mmol of intermediate c-1 and 20 mL of anhydrous tetrahydrofuran to a three-necked flask. Add 12 mmol of a n-butyllithium solution in n-hexane dropwise at 0°C. After reacting for 1 hour, add starting material F-1 and continue reacting at 0°C for 3 hours. Slowly restore the reaction to room temperature for 3 hours, then add 2 mL of water to quench the reaction. Concentrate the reaction solution and recrystallize from ethanol:dichloromethane to obtain intermediate d-1. LC-MS: Measured value: 635.35 ([M+H) + ).

[0134] 5. Add 10 mmol of intermediate d-1, 0.1 mmol of NaOH, and 15 ml of ethanol solution to a three-necked flask and react at room temperature for 5 hours. After the reaction is complete, reduce the pressure and concentrate the organic layer, then purify it by silica gel column chromatography to obtain intermediate e-1.

[0135] 6. Under nitrogen protection, 20 mmol of intermediate a-1, 20 mmol of intermediate e-1, 32 ml of DMF, 20 mmol of potassium carbonate, and 0.3 mmol of CuI were added to a three-necked flask, and the mixture was refluxed for 20 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate f-1. LC-MS: Measured value: 909.31 ([M+H)) + ).

[0136] 7. Intermediate f-1 (5.0 mmol) and tert-butylbenzene (50 mL) were added sequentially to a sealed pressure-resistant tube. The temperature was lowered to -78 °C, and a hexane solution of n-butyllithium (5.5 mmol) was slowly added. The mixture was then stirred and brought to room temperature. Subsequently, the hexane was removed under negative pressure at 60 °C. Nitrogen protection was then introduced, and after reacting for 2 hours, BBr3 (6.0 mmol) was added at -45 °C. The temperature was maintained and stirred for 4 hours, and then slowly restored to room temperature. After stirring at room temperature for 12 hours, DIPEA (N,N-diisopropylethylamine) (10 mmol) was added under ice-water bath conditions, and the mixture was heated to 150 °C and refluxed for 35 hours. The reaction was cooled to room temperature, and the solution was filtered through diatomaceous earth. The organic phase was collected, and the high-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography. Toluene was used as the developing solvent to obtain compound 6. (1 × 10⁻⁶) -5 M) Full width at half maximum (FWHM) 24 nm (obtained by Horiba Fluorolog-3 series fluorescence spectrometer).

[0137] Example 2: Synthesis of Compound 8:

[0138]

[0139] Under nitrogen protection, 10 mmol of starting material C-1, 10 mmol of starting material B-2, 12 mL of cesium carbonate, and 20 mL of anhydrous tetrahydrofuran were added to a three-necked flask, and the reaction was carried out at 150°C for 24 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-2. LC-MS: Measured value: 411.49 ([M+H)) + ).

[0140] Under nitrogen protection, 10 mmol of intermediate a-2, 10 mmol of starting material E-1, and 20 mL of trifluoroacetic acid solution were added to a three-necked flask, and the reaction was carried out at low temperature for 3 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-2. LC-MS: Measured value: 495.44 ([M+H)) + ).

[0141] 10 mmol of intermediate b-2 and 20 mL of anhydrous tetrahydrofuran were added to a three-necked flask. A 12 mmol solution of n-butyllithium in n-hexane was added dropwise at 0°C. After reacting for 1 hour, starting material C-2 was added, and the reaction was continued at 0°C for another 3 hours. The mixture was then slowly brought to room temperature for 3 hours, after which 2 mL of water was added to quench the reaction. The reaction solution was concentrated and recrystallized from ethanol:dichloromethane to obtain intermediate c-2.

[0142] 10 mmol of intermediate c-2, 0.15 mmol of NaOH, and 15 mL of ethanol solution were added to a three-necked flask, and the mixture was reacted at room temperature for 5 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate d-2. LC-MS: Measured value: 607.22 ([M+H)) + ).

[0143] Under nitrogen protection, 20 mmol of intermediate d-2, 20 mmol of intermediate a-1, 40 ml of DMF, 22 mmol of potassium carbonate, and 0.5 mmol of CuI were added to a three-necked flask, and the mixture was refluxed for 25 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate e-2. LC-MS: Measured value: 965.48 ([M+H)) + ).

[0144] Intermediate e-2 (10.0 mmol) and tert-butylbenzene (50 mL) were added sequentially to a sealed pressure-resistant tube. The temperature was lowered to -70 °C, and a hexane solution of n-butyllithium (5.5 mmol) was slowly added. The mixture was then stirred and brought to room temperature. Subsequently, the hexane was removed under negative pressure at 60 °C. Nitrogen protection was then introduced, and after 2 hours of reaction, BBr3 (6.0 mmol) was added at -48 °C. The temperature was maintained and stirred for 4 hours, and then slowly restored to room temperature. After stirring at room temperature for 10 hours, DIPEA (N,N-diisopropylethylamine) (10 mmol) was added under ice-water bath conditions, and the mixture was heated to 150 °C and refluxed for 30 hours. The reaction was cooled to room temperature, and the solution was filtered through diatomaceous earth. The organic phase was collected, and the high-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography using toluene as the developing solvent to obtain compound 8. (1 × 10⁻⁶) -5 M) Full width at half maximum (FWHM) 22 nm (obtained by Horiba Fluorolog-3 series fluorescence spectrometer).

[0145] Example 3: Synthesis of Compound 12:

[0146]

[0147] Under nitrogen protection, 10 mmol of starting material A-3, 10 mmol of potassium iodide, 20 mL of hydrochloric acid, and 13 mmol of sodium nitrite were added to a three-necked flask, and the reaction was carried out at room temperature for 8 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-3. LC-MS: Measured value: 338.99 ([M+H)) + ).

[0148] Under nitrogen protection, a mixed solvent of 10 mmol intermediate a-3, 10 mmol starting material B-3, 0.2 mmol dichloro[1,1'-bis(diphenylphosphine)ferrocene]palladium, 10 mmol potassium carbonate, 30 mmol 1,4-dioxane, and water was reacted at 80°C for 4 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-3. LC-MS: Measured value: 345.12 ([M+H) + ).

[0149] Under nitrogen protection, 10 mmol of intermediate b-3, 10 mmol of starting material C-3, 0.3 mmol of dichloro[1,1'-bis(diphenylphosphine)ferrocene]palladium, 10 mmol of potassium acetate, and 30 mmol of 1,4-dioxane solvent were reacted at 90°C for 5 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-3. LC-MS: Measured value: 393.49 ([M+H))+ ).

[0150] Under nitrogen protection, a mixed solvent of 10 mmol intermediate c-3, 10 mmol starting material D-3, 0.3 mmol dichloro[1,1'-bis(diphenylphosphine)ferrocene]palladium, 12 mmol potassium carbonate, 50 mmol 1,4-dioxane, and water was reacted at 80°C for 4 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate d-3. LC-MS: Measured value: 457.21 ([M+H) + ).

[0151] Under nitrogen protection, 10 mmol of intermediate d-3, 10 mmol of starting material E-3, 12 mL of trifluoroacetic acid, and 5 mL of dichloromethane were added to a three-necked flask, and the reaction was carried out at room temperature for 2 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate e-3. LC-MS: Measured value: 587.18 ([M+H)) + ).

[0152] Under nitrogen protection, 20 mmol of intermediate e-3, 20 mmol of intermediate e-1, 20 mL of DMF, 12 mmol of potassium carbonate, and 0.2 mmol of CuI were added to a three-necked flask, and the mixture was refluxed for 25 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate f-3.

[0153] Intermediate f-3 (10.0 mmol) and tert-butylbenzene (50 mL) were added sequentially to a sealed pressure-resistant tube. The temperature was lowered to -66 °C, and a hexane solution of n-butyllithium (5.5 mmol) was slowly added. The mixture was then stirred and brought to room temperature. Subsequently, the hexane was removed under negative pressure at 65 °C. Nitrogen protection was then introduced, and after 2 hours of reaction, BBr3 (6.0 mmol) was added at -48 °C. The temperature was maintained and stirred for 4 hours, and then slowly restored to room temperature. After stirring at room temperature for 10 hours, DIPEA (N,N-diisopropylethylamine) (10 mmol) was added under ice-water bath conditions, and the mixture was heated to 146 °C and refluxed for 25 hours. The reaction was cooled to room temperature, and the solution was filtered through diatomaceous earth. The organic phase was collected, and the high-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography using toluene as the developing solvent to obtain compound 12. - 5 M) Full width at half maximum (FWHM) 25 nm (obtained by Horiba Fluorolog-3 series fluorescence spectrometer).

[0154] Example 4: Synthesis of Compound 20:

[0155]

[0156] Under nitrogen protection, 10 mmol of starting material B-1, 10 mmol of starting material A-4, 20 ml of DMF, 13 mmol of silver nitrate, 13 mmol of potassium carbonate, and 0.2 mmol of palladium diacetate were added to a three-necked flask, and the reaction was carried out at 120 °C for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-4. LC-MS: Measured value: 602.15 ([M+H)) + ).

[0157] Under nitrogen protection, 10 mmol of intermediate a-4, 10 mmol of intermediate e-1, 20 mL of DMF, 13 mmol of potassium carbonate, and 0.2 mmol of CuI were added to a three-necked flask, and the mixture was refluxed for 27 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-4.

[0158] Intermediate b-4 (5.0 mmol) and tert-butylbenzene (50 mL) were added sequentially to a sealed pressure-resistant tube. The temperature was lowered to -68 °C, and a hexane solution of n-butyllithium (5.0 mmol) was slowly added. The mixture was then stirred and brought to room temperature. Subsequently, the hexane was removed under negative pressure at 68 °C. Nitrogen protection was then introduced, and after 2 hours of reaction, BBr3 (6.0 mmol) was added at -48 °C. The temperature was maintained and stirred for 8 hours, and then slowly restored to room temperature. After stirring at room temperature for 20 hours, DIPEA (N,N-diisopropylethylamine) (10 mmol) was added under ice-water bath conditions, and the mixture was heated to 150 °C and refluxed for 25 hours. The reaction was cooled to room temperature, and the solution was filtered through diatomaceous earth. The organic phase was collected, and the high-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography. Toluene was used as the developing solvent to obtain compound 20. (1 × 10⁻⁶) - 5 M) Full width at half maximum (FWHM) 23 nm (obtained by Horiba Fluorolog-3 series fluorescence spectrometer).

[0159] Example 5: Synthesis of Compound 72:

[0160]

[0161] Under nitrogen protection, 10 mmol of starting material F-1, 10 mmol of starting material A-5, 18 ml of 1,2-dibromoethane, and 20 mmol of THF were added to a three-necked flask, and the mixture was refluxed for 20 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-5. LC-MS: Measured value: 431.47 ([M+H)) + ).

[0162] 10 mmol of intermediate a-5, 10 mmol of starting material B-5, 18 ml of boron trifluoride ether, 20 mmol of diethyl ether, and 20 mmol of dichloromethane were added to a three-necked flask and reacted at room temperature for 2 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-5. LC-MS: Measured value: 547.36 ([M+H)) + ).

[0163] Under nitrogen protection, 10 mmol of intermediate b-5, 10 mmol of intermediate e-1, 0.049 mmol of dipalladium(O)tris(dibenzylacetone), 0.32 mmol of tri-tert-butylphosphine, and 5 mL of o-xylene were stirred at 60 °C for 20 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-5.

[0164] Intermediate C-5 (5.0 mmol) and tert-butylbenzene (50 mL) were added sequentially to a sealed pressure-resistant tube. The temperature was lowered to -68 °C, and a hexane solution of n-butyllithium (5.0 mmol) was slowly added. The mixture was then stirred and brought to room temperature. Subsequently, the hexane was removed under negative pressure at 75 °C. Nitrogen protection was then introduced, and after 2 hours of reaction, BBr3 (6.0 mmol) was added at -55 °C. The temperature was maintained and stirred for 10 hours. The temperature was then slowly restored to room temperature, and after stirring at room temperature for 24 hours, DIPEA (N,N-diisopropylethylamine) (10 mmol) was added under ice-water bath conditions. The mixture was then heated to 150 °C and refluxed for 28 hours. The reaction was cooled to room temperature, and the solution was filtered through diatomaceous earth. The organic phase was collected, and the high-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography using toluene as the developing solvent to obtain compound 72. (1 × 10⁻⁶) - 5 M) Full width at half maximum (FWHM) 24 nm (obtained by Horiba Fluorolog-3 series fluorescence spectrometer).

[0165] Example 6: Synthesis of Compound 130:

[0166]

[0167]

[0168] Under nitrogen protection, 10 mmol of starting material A-6, 10 mmol of starting material C-3, 0.4 mmol of dichloro[1,1'-bis(diphenylphosphine)ferrocene]palladium, 10 mmol of potassium acetate, and 28 mmol of 1,4-dioxane solvent were reacted at 85°C for 6 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-6.

[0169] Under nitrogen protection, a mixed solvent of 10 mmol intermediate a-6, 10 mmol starting material D-3, 0.3 mmol dichloro[1,1'-bis(diphenylphosphine)ferrocene]palladium, 12 mmol potassium carbonate, 50 mmol 1,4-dioxane, and water was reacted at 80°C for 5 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-6.

[0170] Under nitrogen protection, 10 mmol of intermediate b-6, 10 mmol of starting material B-6, 12 ml of trifluoroacetic acid, and 5 ml of dichloromethane were added to a three-necked flask, and the reaction was carried out at room temperature for 2 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-6.

[0171] 10 mmol of intermediate C-1 and 20 mL of anhydrous tetrahydrofuran were added to a three-necked flask. A solution of 15 mmol of n-butyllithium in n-hexane was added dropwise at 0°C. After reacting for 1.5 hours, starting material C-6 was added, and the reaction was continued at 0°C for another 4 hours. The reaction was then slowly brought to room temperature for 4 hours, after which 3 mL of water was added to quench the reaction. The reaction solution was concentrated and recrystallized from ethanol:dichloromethane to obtain intermediate d-6. LC-MS: Measured value: 605.38 ([M+H)) + ).

[0172] 10 mmol of intermediate d-6, 0.2 mmol of NaOH, and 16 mL of ethanol solution were added to a three-necked flask and reacted at room temperature for 8 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate e-6. LC-MS: Measured value: 521.35 ([M+H)) + ).

[0173] Under nitrogen protection, 10 mmol of intermediate e-6, 10 mmol of intermediate c-6, 25 mL of DMF, 13 mmol of potassium carbonate, and 0.2 mmol of CuI were added to a three-necked flask, and the mixture was refluxed for 25 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate f-6. LC-MS: Measured value: 1011.90 ([M+H)) + ).

[0174] Intermediate f-6 (5.0 mmol) and tert-butylbenzene (50 mL) were added sequentially to a sealed pressure-resistant tube. The temperature was lowered to -58 °C, and a hexane solution of n-butyllithium (5.0 mmol) was slowly added. The mixture was then stirred and brought to room temperature. Subsequently, the hexane was removed under negative pressure at 72 °C. Nitrogen protection was then introduced, and after 8 hours of reaction, BBr3 (6.0 mmol) was added at -59 °C. The temperature was maintained and stirred for 18 hours. The temperature was then slowly restored to room temperature, and after stirring at room temperature for 32 hours, DIPEA (N,N-diisopropylethylamine) (10 mmol) was added under ice-water bath conditions. The mixture was then heated to 120 °C and refluxed for 35 hours. The reaction was cooled to room temperature, and the solution was filtered through diatomaceous earth. The organic phase was collected, and the high-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography using toluene as the developing solvent to obtain compound 130. - 5 M) Full width at half maximum (FWHM) 25 nm (obtained by Horiba Fluorolog-3 series fluorescence spectrometer).

[0175] Example 7: Synthesis of Compound 191:

[0176]

[0177] Under nitrogen protection, 10 mmol of starting material A-7, 10 mmol of starting material E-1, and 20 mL of trifluoroacetic acid solution were added to a three-necked flask, and the reaction was carried out at low temperature for 5 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-7. LC-MS: Measured value: 417.30 ([M+H)) + ).

[0178] 10 mmol of intermediate a-7 and 20 mL of anhydrous tetrahydrofuran were added to a three-necked flask. A solution of 14 mmol of n-butyllithium in n-hexane was added dropwise at 0°C. After reacting for 1.5 hours, starting material F-1 was added, and the reaction was continued at 0°C for another 4 hours. The reaction was then slowly brought to room temperature for 4 hours, after which 2 mL of water was added to quench the reaction. The reaction solution was concentrated and recrystallized from ethanol:dichloromethane to obtain intermediate b-7. LC-MS: Measured value: 579.22 ([M+H) + ).

[0179] 10 mmol of intermediate b-7, 0.15 mmol of NaOH, and 20 mL of ethanol solution were added to a three-necked flask and reacted at room temperature for 6 hours. After the reaction was complete, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-7. LC-MS: Measured value: 495.37 ([M+H)) + ).

[0180] Under nitrogen protection, 10 mmol of intermediate c-7, 10 mmol of intermediate a-1, 20 mL of DMF, 12 mmol of potassium carbonate, and 0.2 mmol of CuI were added to a three-necked flask, and the mixture was refluxed for 28 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate d-7. LC-MS: Measured value: 853.20 ([M+H)) + ).

[0181] Intermediate d-7 (10.0 mmol) and tert-butylbenzene (80 mL) were added sequentially to a sealed pressure-resistant tube. The temperature was lowered to -72 °C, and a hexane solution of n-butyllithium (10.0 mmol) was slowly added. The mixture was then stirred and brought to room temperature. Subsequently, the hexane was removed under negative pressure at 70 °C. Nitrogen protection was then introduced, and after 8 hours of reaction, BBr3 (10.0 mmol) was added at -66 °C. The temperature was maintained and stirred for 15 hours, then slowly restored to room temperature. After stirring at room temperature for 30 hours, DIPEA (N,N-diisopropylethylamine) (10 mmol) was added under ice-water bath conditions, and the mixture was heated to 130 °C and refluxed for 30 hours. The reaction was cooled to room temperature, and the solution was filtered through diatomaceous earth. The organic phase was collected, and the high-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography using toluene as the developing solvent to obtain compound 191. - 5 M) Full width at half maximum (FWHM) 23 nm (obtained by Horiba Fluorolog-3 series fluorescence spectrometer).

[0182] Example 8: Synthesis of Compound 268:

[0183]

[0184] 10 mmol of intermediate a-7 and 20 mL of anhydrous tetrahydrofuran were added to a three-necked flask. A solution of 15 mmol of n-butyllithium in n-hexane was added dropwise at 0°C. After reacting for 1.5 hours, starting material A-6 was added, and the reaction was continued at 0°C for another 6 hours. After slowly restoring to room temperature for 6 hours, the reaction was quenched by adding 2 mL of water. The reaction solution was concentrated and recrystallized from ethanol:dichloromethane to obtain intermediate a-8.

[0185] 10 mmol of intermediate a-8, 0.25 mmol of NaOH, and 30 mL of ethanol solution were added to a three-necked flask and reacted at room temperature for 8 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-8. LC-MS: Measured value: 465.42 ([M+H)) + ).

[0186] Under nitrogen protection, 10 mmol of intermediate b-8, 10 mmol of intermediate a-4, 30 mL of DMF, 15 mmol of potassium carbonate, and 0.25 mmol of CuI were added to a three-necked flask, and the mixture was refluxed for 26 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-8. LC-MS: Measured value: 1046.34 ([M+H)) + ).

[0187] Intermediate C-8 (10.0 mmol) and tert-butylbenzene (90 mL) were added sequentially to a sealed pressure-resistant tube. The temperature was lowered to -65 °C, and a hexane solution of n-butyllithium (10.0 mmol) was slowly added. The mixture was then stirred and brought to room temperature. Subsequently, the hexane was removed under negative pressure at 62 °C. Nitrogen protection was then introduced, and after 9 hours of reaction, BBr3 (10.0 mmol) was added at -68 °C. The temperature was maintained and stirred for 10 hours, then slowly restored to room temperature. After stirring at room temperature for 20 hours, DIPEA (N,N-diisopropylethylamine) (10 mmol) was added under ice-water bath conditions, and the mixture was heated to 135 °C and refluxed for 33 hours. The reaction was cooled to room temperature, and the solution was filtered through diatomaceous earth. The organic phase was collected, and the high-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography using toluene as the developing solvent to obtain compound 268. - 5 M) Full width at half maximum (FWHM) 24 nm (obtained by Horiba Fluorolog-3 series fluorescence spectrometer).

[0188] Example 9: Synthesis of Compound 77:

[0189]

[0190]

[0191] Under nitrogen protection, 10 mmol of starting material A-9, 10 mmol of starting material B-9, 0.35 mmol of dichloro[1,1'-bis(diphenylphosphine)ferrocene]palladium, 10 mmol of potassium acetate, and 40 mmol of 1,4-dioxane solvent were reacted at 90°C for 8 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-9.

[0192] Under nitrogen protection, 10 mmol of intermediate a-9, 10 mmol of starting material E-1, and 30 mL of trifluoroacetic acid solution were added to a three-necked flask, and the reaction was carried out at low temperature for 8 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-9. LC-MS: Measured value: 507.26 ([M+H]+).

[0193] 10 mmol of intermediate b-9 and 20 mL of anhydrous tetrahydrofuran were added to a three-necked flask. A 16 mmol solution of n-butyllithium in n-hexane was added dropwise at 0°C. After reacting for 3 hours, starting material F-1 was added, and the reaction was continued at 0°C for another 6 hours. The reaction was then slowly brought to room temperature for 4 hours, after which 2 mL of water was added to quench the reaction. The reaction mixture was concentrated and recrystallized from ethanol:dichloromethane to obtain intermediate c-9.

[0194] 10 mmol of intermediate c-9, 0.2 mmol of NaOH, and 25 mL of ethanol solution were added to a three-necked flask and reacted at room temperature for 7 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate d-9. LC-MS: Measured value: 551.30 ([M+H]+).

[0195] Under nitrogen protection, 10 mmol of intermediate d-9, 10 mmol of intermediate c-6, 20 mL of DMF, 13 mmol of potassium carbonate, and 0.2 mmol of CuI were added to a three-necked flask, and the mixture was refluxed for 30 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate e-9. LC-MS: Measured value: 1132.45 ([M+H]+).

[0196] Intermediate e-9 (10.0 mmol) and tert-butylbenzene (85 mL) were added sequentially to a sealed pressure-resistant tube. The temperature was lowered to -75 °C, and a hexane solution of n-butyllithium (10.0 mmol) was slowly added. The mixture was then stirred and brought to room temperature. Subsequently, the hexane was removed under negative pressure at 75 °C. Nitrogen protection was then introduced, and after 8 hours of reaction, BBr3 (10.0 mmol) was added at -68 °C. The temperature was maintained and stirred for 20 hours. The temperature was then slowly restored to room temperature, and after stirring at room temperature for 30 hours, DIPEA (N,N-diisopropylethylamine) (10 mmol) was added under ice-water bath conditions. The mixture was then heated to 120 °C and refluxed for 30 hours. The reaction was cooled to room temperature, and the solution was filtered through diatomaceous earth. The organic phase was collected, and the high-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography. Toluene was used as the developing solvent to give compound 77. - 5 M) Full width at half maximum (FWHM) 23 nm (obtained by Horiba Fluorolog-3 series fluorescence spectrometer).

[0197] Example 10 Synthesis of compound 213:

[0198]

[0199]

[0200] Under nitrogen protection, 10 mmol of starting material A-10, 10 mmol of starting material C-3, 0.5 mmol of dichloro[1,1'-bis(diphenylphosphine)ferrocene]palladium, 10 mmol of potassium acetate, and 29 mmol of 1,4-dioxane solvent were reacted at 88°C for 9 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-10. LC-MS: 261.37 ([M+H]+).

[0201] Under nitrogen protection, a mixed solvent of 10 mmol intermediate a-10, 10 mmol starting material D-3, 0.35 mmol dichloro[1,1'-bis(diphenylphosphine)ferrocene]palladium, 13 mmol potassium carbonate, 50 mmol 1,4-dioxane, and water was reacted at 80°C for 7 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-10. LC-MS: 325.46 ([M+H]+).

[0202] Under nitrogen protection, 10 mmol of intermediate b-10, 10 mmol of starting material B-6, 12 ml of trifluoroacetic acid, and 6 ml of dichloromethane were added to a three-necked flask, and the reaction was carried out at room temperature for 3 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-10. LC-MS: Measured value: 455.14 ([M+H]+).

[0203] Under nitrogen protection, 10 mmol of starting material B-10, 10 mmol of starting material E-1, and 25 ml of trifluoroacetic acid solution were added to a three-necked flask, and the reaction was carried out at low temperature for 5 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate d-10. LC-MS: Measured value: 341.11 ([M+H]+).

[0204] Under nitrogen protection, 10 mmol of intermediate d-10, 10 mmol of starting material B-2, 13 mL of cesium carbonate, and 20 mL of anhydrous tetrahydrofuran were added to a three-necked flask, and the reaction was carried out at 150°C for 26 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate e-10. LC-MS: 495.03 ([M+H]+).

[0205] 10 mmol of intermediate e-10 and 20 mL of anhydrous tetrahydrofuran were added to a three-necked flask. A solution of 15 mmol of n-butyllithium in n-hexane was added dropwise at 0°C. After reacting for 1.5 hours, starting material F-1 was added, and the reaction was continued at 0°C for another 3 hours. After slowly restoring to room temperature for 5 hours, 2 mL of water was added to quench the reaction. The reaction solution was concentrated and recrystallized from ethanol:dichloromethane to obtain intermediate f-10. LC-MS: Measured value: 581.47 ([M+H]+).

[0206] 10 mmol of intermediate f-10, 0.2 mmol of NaOH, and 20 mL of ethanol solution were added to a three-necked flask and reacted at room temperature for 4 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate g-10. LC-MS: Measured value: 497.42 ([M+H]+).

[0207] Under nitrogen protection, 20 mmol of intermediate g-10, 20 mmol of intermediate c-10, 45 ml of DMF, 25 mmol of potassium carbonate, and 0.5 mmol of CuI were added to a three-necked flask, and the mixture was refluxed for 28 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate h-10.

[0208] Intermediate h-10 (10.0 mmol) and tert-butylbenzene (55 mL) were added sequentially to a sealed pressure-resistant tube. The temperature was lowered to -78 °C, and a hexane solution of n-butyllithium (5.5 mmol) was slowly added. The mixture was then stirred and brought to room temperature. Subsequently, the hexane was removed under negative pressure at 60 °C. Nitrogen protection was then introduced, and after 2 hours of reaction, BBr3 (6.0 mmol) was added at -46 °C. The temperature was maintained and stirred for 6 hours, and then slowly restored to room temperature. After stirring at room temperature for 10 hours, DIPEA (N,N-diisopropylethylamine) (10 mmol) was added under ice-water bath conditions, and the mixture was heated to 150 °C and refluxed for 30 hours. The reaction was cooled to room temperature, and the solution was filtered through diatomaceous earth. The organic phase was collected, and the high-boiling solvent was removed by vacuum distillation. The solution was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography using toluene as the developing solvent to obtain compound 213. -5 M) Full width at half maximum (FWHM) 24 nm (obtained by Horiba Fluorolog-3 series fluorescence spectrometer).

[0209] The structural characterization of the compounds obtained in each embodiment is shown in Table 1.

[0210] Table 1

[0211]

[0212] The compounds of this invention can be used as doping materials for the light-emitting layer in light-emitting devices.

[0213] The application effects of the OLED materials synthesized in this invention in devices are described in detail below through device examples 1-10 and device comparative examples 1-3. Device examples 2-10 and device comparative examples 1-3 of this invention have the same fabrication process as device example 1, and use the same substrate and electrode materials, with consistent electrode film thickness. The only difference is the replacement of the light-emitting layer material in the device. The layer structure and test results of each device example are shown in Tables 2-1 and 3, respectively:

[0214] Device Example 1

[0215] like Figure 1 As shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, 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 OLED light-emitting device is fabricated, using GH-1 and GH-2 as the host materials and compound 6 as the dopant material, with a mass ratio of GH-1, GH-2, and compound 6 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.

[0216] The application effects of the OLED materials synthesized in this invention in devices are described in detail below using device examples 11-20 and device comparative examples 4-6. Device examples 11-20 and device comparative examples 4-6 of this invention have the same fabrication process as device example 11, and use the same substrate and electrode materials, with consistent electrode film thickness. The only difference is the replacement of the light-emitting layer material in the device. The layer structures and test results of each device example are shown in Tables 2-2 and 3, respectively.

[0217] Device Example 11

[0218] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed sequentially with a cleaning agent (Semiclean M-L20), followed by washing with pure water, drying, and then ultraviolet-ozone washing to remove organic residues from the transparent ITO surface. After the above washing, a 10nm thick layer of HT-1 and HI-1 is deposited on the ITO anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3, with a mass ratio of HT-1 to HI-1 of 97:3. Next, a 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 OLED light-emitting device is fabricated, using GH-1 and GH-2 as the host materials, GD-1 as the first dopant, and compound 6 as the second dopant, with a mass ratio of GH-1, GH-2, GD-1, and compound 6 of 66:30:3:1. The light-emitting layer has a film thickness of 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.

[0219] The molecular structural formulas of the relevant materials are shown below:

[0220]

[0221] After completing the OLED light-emitting device as described above, the anode and cathode are connected using a known driving circuit, and the current efficiency, external quantum 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, external quantum efficiency, and lifetime of the obtained devices are shown in Table 3.

[0222] Table 2-1

[0223]

[0224]

[0225] Table 2-2

[0226]

[0227]

[0228] Table 3

[0229]

[0230] Note: Voltage, current efficiency, and emission peak were measured using an IVL (current-voltage-brightness) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.); the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are within 10 mA / cm². 2 Next test.

[0231] As can be seen from the device data results in Table 3, this framework compound, while achieving green light emission, exhibits high efficiency and long lifetime, and the material also demonstrates excellent stability. Compared with devices in Comparative Examples 1-6, the current efficiency and device lifetime of the organic light-emitting device of the present invention are significantly improved compared to OLED devices made of known materials; when using an exciton-sensitized material as the first dopant, the device efficiency is significantly improved compared to single-doped devices. 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 scope of protection of the present invention.

Claims

1. A boron-containing organic compound, characterized in that, The structure of the boron-containing organic compound is shown in any one of general formulas (81) to (86): In general formulas (81)-(86), M1, M3, M5, and M7 are each independently represented as a substituted indole group or any of the following ring structures: M2, M4, M6, and M8 can be independently represented as any of the following ring structures: Z is represented as C-R1; X is represented as N-R2, O, S; Each occurrence of R1, whether identical or different, represents a hydrogen atom, deuterium atom, halogen atom, or substituted or unsubstituted C1-C1 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, phenyl-substituted amino groups, tert-butylbenzene-substituted amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Each occurrence of the same or different R2 indicates substituted or unsubstituted C3-C3. 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Z1 is represented as CR a Z2 is represented as CR b Z3 is represented as CR c Z4 is represented as CR d Z5 is represented as CR e ; R a R b R c R d R e Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, halogen atom, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, phenyl-substituted amino groups, tert-butylbenzene-substituted amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

2. A boron-containing organic compound, characterized in that, The structure of the boron-containing organic compound is shown in any one of general formulas (87) to (93): In general formulas (87) to (93), Z is represented as C-R1; X is represented as N-R2, O, S; Each occurrence of R1, whether identical or different, represents a hydrogen atom, deuterium atom, halogen atom, or substituted or unsubstituted C1-C1 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, phenyl-substituted amino groups, tert-butylbenzene-substituted amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Each occurrence of the same or different R2 indicates substituted or unsubstituted C3-C3. 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Z1 is represented as CR a Z2 is represented as CR b Z3 is represented as CR c Z4 is represented as CR d Z5 is represented as CR e ; R a R b R c R d R e Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, halogen atom, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, phenyl-substituted amino groups, tert-butylbenzene-substituted amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Z6 is represented as CR f Z7 is represented as CR g ; R f R g Each instance of the same or different element is represented by a hydrogen atom, deuterium atom, halogen atom, or substituted or unsubstituted C1-C. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, phenyl-substituted amino groups, tert-butylbenzene-substituted amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

3. A boron-containing organic compound, characterized in that, The structure of the boron-containing organic compound is shown in any one of general formulas (9), (11) to (17), (19) to (22), and (27): In general formulas (9), (11) to (17), (19) to (22), and (27), Z is represented as C-R1; X is represented as N-R2, O, S; Each occurrence of R1, whether identical or different, represents a hydrogen atom, deuterium atom, halogen atom, or substituted or unsubstituted C1-C1 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, phenyl-substituted amino groups, tert-butylbenzene-substituted amino groups, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; Each occurrence of the same or different R2 indicates substituted or unsubstituted C3-C3. 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

4. The boron-containing organic compound according to claim 3, characterized in that, The structure of the organic compound is shown in any one of general formulas (33), (37) to (40): In general formulas (33), (37) to (40), Z is represented as C-R1; X is represented as N-R2, O, S; R1 appearing repeatedly, whether the same or different, represents hydrogen atom, halogen atom, deuterium atom, cyano group, or C1-C. 10 Alkyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 One of the heteroaryl groups; Each occurrence of the same or different R2 indicates substituted or unsubstituted C3-C3. 10 Cycloalkyl, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C2-C 30 One of the heteroaryl groups; The substituents used for the substituent groups are optionally selected from halogen atoms, deuterium atoms, cyano groups, C1-C... 10 Alkyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

5. The boron-containing organic compound according to claim 3, characterized in that, The structure of the boron-containing organic compound is shown in any one of general formulas (41), (43) to (48), (56), (58) to (63), (71) to (74): In general formulas (41), (43) to (48), (56), (58) to (63), (71) to (74), Z is represented as C-R1; R1 appearing repeatedly, whether the same or different, represents hydrogen atom, halogen atom, deuterium atom, cyano group, or C1-C. 10 Alkyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 One of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

6. The boron-containing organic compound according to claim 3, characterized in that, The structure of the boron-containing organic compound is shown in any one of general formula (49), general formula (51) to general formula (55), and general formula (65) to general formula (69): In general formulas (49), (51) to (55), (65) to (69), Z is represented as C-R1; R1 appearing repeatedly, whether the same or different, represents hydrogen atom, halogen atom, deuterium atom, cyano group, or C1-C. 10 Alkyl, C1-C 10 alkoxy groups, C3-C 20 cycloalkyl, C6-C 30 Aryl, C3-C 30 One of the heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

7. The boron-containing organic compound according to claim 1, characterized in that, The R1, R a R b R c R d R e Each of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, and isopropyl-substituted. The following is a list of phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boraneyl, methoxy, and tert-butoxy. R2 represents phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl One of the following: biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tert-butyl-substituted dibenzofuranyl, oxanthoneyl, and phenyl-substituted triazineyl.

8. The boron-containing organic compound according to claim 2, characterized in that, The R1, R a R b R c R d R e R f R g Each of these can be independently represented as a hydrogen atom, deuterium atom, halogen atom, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, and isopropyl-substituted. The following is a list of phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boraneyl, methoxy, and tert-butoxy. R2 represents phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl One of the following: biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tert-butyl-substituted dibenzofuranyl, oxanthoneyl, and phenyl-substituted triazineyl.

9. The boron-containing organic compound according to claim 3, characterized in that, R1 is independently represented as hydrogen atom, deuterium atom, halogen atom, adamantyl, methyl, deuterated methyl, trifluoromethyl, ethyl, deuterated ethyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl The substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl, ethyl-substituted diphenyl, isopropyl-substituted diphenyl, tert-butyl-substituted diphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted diphenyl, deuterated ethyl-substituted diphenyl, deuterated isopropyl-substituted diphenyl, deuterated tert-butyl-substituted diphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthoneyl, phenyl-substituted triazineyl, phenyl-substituted boronyl, methoxy, tert-butoxy; R2 represents phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl One of the following: biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tert-butyl-substituted dibenzofuranyl, oxanthoneyl, and phenyl-substituted triazineyl.

10. The boron-containing organic compound according to claim 4, characterized in that, R1 is independently represented by one of the following: hydrogen atom, deuterium atom, halogen atom, adamantyl, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, diphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, and xanthoneyl. R2 represents phenyl, deuterated phenyl, diphenyl, deuterated diphenyl, terphenyl, deuterated terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted diphenyl One of the following: biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tert-butyl-substituted dibenzofuranyl, oxanthoneyl, and phenyl-substituted triazineyl.

11. The boron-containing organic compound according to claim 5, characterized in that, R1 is independently represented by one of the following: hydrogen atom, deuterium atom, halogen atom, adamantyl, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, diphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, and xanthoneyl.

12. The boron-containing organic compound according to claim 6, characterized in that, R1 is independently represented by one of the following: hydrogen atom, deuterium atom, halogen atom, adamantyl, methyl, ethyl, isopropyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, diphenyl, terphenyl, naphthyl, anthracene, phenanthryl, pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, dibenzofuranyl, dibenzothiophene, carbazoyl, N-phenylcarbazoyl, 9,9-dimethylfluorenyl, spirofluorenyl, and xanthoneyl.

13. A boron-containing organic compound, characterized in that, The organic compound has a specific structure that is any one of the following:

14. An organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, said organic light-emitting functional layer comprising a light-emitting layer, characterized in that, The light-emitting layer contains a boron-containing organic compound as described in any one of claims 1-13.

15. The organic electroluminescent device according to claim 14, characterized in that, The light-emitting layer comprises a host material and a dopant material, wherein the dopant material contains a boron-containing organic compound as described in any one of claims 1-13.

16. The organic electroluminescent device according to claim 14, 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 and second main materials is a TADF material, and the doping material is a boron-containing organic compound as described in any one of claims 1-13.

17. The organic electroluminescent device according to claim 14, 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 organic compound as described in any one of claims 1-13.

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