A boron-containing organic compound containing cyclohexanecarbazole ring and an organic electroluminescent device prepared therefrom

Abstract

The present invention discloses a boron-containing organic compound containing a cyclohexanecarbazole ring and an organic electroluminescent device prepared therefrom, belonging to the field of semiconductor technology. The structures of the organic compound of the present invention are shown in general formulas (1) and (2). When used as a dopant material in the light-emitting layer material of an OLED light-emitting device, the compound of the present invention can be used as a green light dopant material in the light-emitting layer of the organic electroluminescent device, thereby improving the color purity and efficiency of the device's emission.

Description

Technical Field

[0001] The present invention relates to the field of semiconductor technology, in particular to a boron-containing organic compound containing cyclohexanecarbazole ring and an organic electroluminescent device prepared therefrom. Background Art

[0002] Traditional fluorescent doping materials, limited by early technology, can only utilize the 25% of singlet excitons formed by electrical excitation to emit light. This results in low internal quantum efficiency (maximum 25%) and external quantum efficiency generally below 5%, significantly lagging behind the efficiency of phosphorescent devices. Phosphorescent materials, due to the strong spin-orbit coupling at the heavy atom center that enhances intersystem crossing, can effectively utilize singlet and triplet excitons formed by electrical excitation to emit light, achieving a device internal quantum efficiency of 100%. However, the high cost of most phosphorescent materials, poor material stability, low color purity, and severe device efficiency roll-off have limited their application in OLEDs.

[0003] With the advent of the 5G era, higher requirements are being placed on color rendering standards. In addition to being efficient and stable, luminescent materials also need to have a narrower half-width to improve the color purity of the device's luminescent color. Fluorescent doping materials can achieve high fluorescence quantum and narrow half-width through molecular engineering. Blue fluorescent doping materials have achieved a phased breakthrough, and the half-width of boron-based materials can be reduced to below 30nm. However, research in the green light region, to which the human eye is more sensitive, has mainly focused on phosphorescent doping materials. However, their luminescent peak shape is difficult to narrow through simple methods. Therefore, to meet higher color rendering standards, it is of great significance to study efficient green fluorescent doping materials with narrow half-width.

[0004] In addition, the sensitization technology combines triplet exciton-sensitizing materials with fluorescent doping materials, uses triplet exciton-sensitizing materials as exciton-sensitizing media, fully utilizes triplet excitons, and transfers energy to fluorescent doping materials through energy transfer, which can also achieve 100% device internal quantum efficiency. This technology can make up for the shortcomings of insufficient exciton utilization of fluorescent doping materials, and effectively give play to the characteristics of high fluorescence quantum yield, high device stability, high color purity and low price of fluorescent doping materials, and has broad prospects in OLEDs applications.

[0005] Boron compounds with resonant structures are more likely to achieve narrow half-width luminescence. Such materials are used in sensitization technology to achieve the preparation of devices with high efficiency and narrow half-width emission. For example, CN 107507921 A and CN 110492006 A disclose a TADF material with a difference between the lowest singlet state and the lowest triplet state energy level of less than or equal to 0.2eV as the main body, and a boron-containing material as the doping luminescent layer combination technology; CN110492005A and CN 110492009 A disclose a luminescent layer combination scheme with an exciplex as the main body and a boron-containing material as the doping; both can achieve efficiency comparable to phosphorescence and a relatively narrow half-width. Therefore, the development of sensitization technology based on narrow half-width boron-based luminescent materials has unique advantages and strong potential in terms of BT.2020 display indicators. Summary of the Invention

[0006] To address the aforementioned issues with the prior art, the present invention provides a boron-containing organic compound containing a cyclohexanecarbazole ring and an organic electroluminescent device prepared therefrom. By introducing a cyclohexanecarbazole ring structure at a specific position within a boron-nitrogen fused ring core, the compound can be used as a green light-emitting dopant in the luminescent layer of an organic electroluminescent device, thereby improving the device's luminescent color purity and lifetime.

[0007] The technical solution of the present invention is as follows: a boron-containing organic compound containing cyclohexanecarbazole ring, the structure of the boron-containing organic compound is shown in general formula (1) and general formula (2):

[0008]

[0009] In the general formula (1) and the general formula (2), R1-R 11 Each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a 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, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0010] R1-R 11 Any two adjacent ones can be bonded to form a ring;

[0011] Ar1 and Ar2 are each independently a hydrogen atom, a deuterium atom, a tritium atom, a methyl group, or CD3;

[0012] M1 represents a substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0013] X represents one of O, S, N(Q1), C(Q2)(Q3), and Si(Q4)(Q5);

[0014] Q1 is independently substituted or unsubstituted C1 to C 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;

[0015] Q1 can also form a ring with M1;

[0016] Q2, Q3, Q4, and Q5 are each independently a 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, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0017] The substituents for the substituent group are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups;

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

[0019] In a preferred embodiment, the structure of the boron-containing organic compound is as shown in any one of the general formulas (3) to (6):

[0020]

[0021] In general formula (3) to general formula (6), X, Ar1, Ar2, R1-R 11 has the same meaning as defined above;

[0022] Y is represented by one of O and S;

[0023] R 12 -R 15Each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a 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, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0024] The substituents for the substituent group are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups;

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

[0026] In a preferred embodiment, the structure of the boron-containing organic compound is as shown in any one of the general formulas (7) to (10):

[0027]

[0028] In general formula (7) to general formula (10), Ar1, Ar2, R1-R 11 has the same meaning as defined above;

[0029] R 12 -R 18 Each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a 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, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0030] The substituents for the substituent group are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups;

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

[0032] In a preferred embodiment, the structure of the boron-containing organic compound is as shown in any one of the general formulas (11) to (14):

[0033]

[0034]

[0035] In general formula (11) to general formula (14), X, R1-R 11 has the same meaning as defined above;

[0036] Y is represented by one of O and S;

[0037] R 12 -R 15 Each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a 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, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0038] The substituents for the substituent group are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups;

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

[0040] In a preferred embodiment, the structure of the boron-containing organic compound is as shown in any one of the general formulas (15) to (38):

[0041]

[0042]

[0043] In general formulas (15) to (38), R2, R5, R6, R9, R 10 has the same meaning as defined above;

[0044] R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 Each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a 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, substituted or unsubstituted arylamine, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups;

[0045] The substituents for the substituent group are selected from deuterium atoms, tritium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups;

[0046] The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

[0047] Preferably, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 They are independently represented as follows:

[0048] Hydrogen atom, cyano group,

[0049] Any of the following;

[0050] The M1 is represented by any one of the following ring structures:

[0051]

[0052]

[0053] The Z is represented by CR a ;

[0054] R a Each occurrence independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a benzyl group phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthrenyl, pyridyl, phenyl-substituted pyridyl, quinolyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl , 9,9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted 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, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boryl, methoxy, tert-butoxy.

[0055] Preferably, R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20Each of the following groups independently represents a hydrogen atom, a deuterium atom, a tritium atom, a cyano group, a halogen atom, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated substituted phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether, methyl substituted diphenyl ether, naphthyl, anthracenyl, phenanthrenyl, pyridyl, phenyl substituted pyridyl, quinolyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9-phenylcarbazolyl , one of 9-dimethylfluorenyl, spirofluorenyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted 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, phenyl-substituted amino, tert-butylphenyl-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, phenyl-substituted boryl, methoxy, and tert-butoxy;

[0056] The M1 is represented by a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a phenyl-substituted amino group, a tert-butyl-substituted dibenzofuranyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group, an isopropyl-substituted phenyl group, a tert-butyl-substituted phenyl group, a methyl-substituted biphenyl group, an ethyl-substituted biphenyl group, an isopropyl-substituted biphenyl group, a tert-butyl-substituted biphenyl group, or a xanthone group;

[0057] The substituents for the substituent group are optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, a trifluoromethyl group, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthrenyl group.

[0058] Preferably, the specific structure of the boron-containing organic compound is any one of the following structures:

[0059]

[0060]

[0061]

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071] The present invention also provides an organic electroluminescent device comprising a cathode and an anode, and an organic light-emitting functional layer therebetween. The organic light-emitting functional layer comprises a light-emitting layer containing the boron-containing organic compound containing cyclohexanecarbazole ring.

[0072] In a preferred embodiment, the light-emitting layer comprises a host material and a doping material, wherein the doping material comprises the boron-containing organic compound containing cyclohexanecarbazole ring.

[0073] In a preferred embodiment, the light-emitting layer comprises a first host material, a second host material and a doping material, at least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing organic compound containing cyclohexanecarbazole and a ring.

[0074] In a preferred embodiment, the light-emitting layer comprises a host material, an exciton-sensitizing material and a doping material. The exciton-sensitizing material is a complex containing a metal element, and the doping material is the boron-containing organic compound containing cyclohexanecarbazole ring.

[0075] The beneficial technical effects of the present invention are:

[0076] (1) The compounds of the present invention are applied to OLED devices and can be used as doping materials for light-emitting layer materials. They can emit green fluorescence under the action of an electric field and can be applied to OLED lighting or OLED display fields.

[0077] (2) The compound of the present invention is used as a doping material, and the TADF sensitizer is introduced as a second host, which can effectively improve the device efficiency;

[0078] (3) The compound of the present invention is used as a doping material and introduced into a phosphorescent sensitizer, which can effectively improve the device efficiency;

[0079] (4) The spectral FWHM of the compound of the present invention is relatively narrow, which can effectively improve the color gamut of the device and enhance the luminous efficiency of the device;

[0080] The compound of the present invention has a narrow half-peak width and a high fluorescence quantum yield, and can be used as a green light doping material of a light-emitting layer of an organic electroluminescent device, thereby improving the luminescent color purity and life of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0081] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in the present invention are applied;

[0082] Among them, 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 DESCRIPTION

[0083] The present invention will be described in detail below with reference to the accompanying drawings and embodiments.

[0084] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, terms such as "upper," "lower," "top," and "bottom" that indicate orientation refer only to a particular state and do not imply that the structure can exist only in the described orientation. Conversely, if the structure can be repositioned, such as inverted, the orientation of the structure will change accordingly. Specifically, in the present invention, the "bottom" or "lower" side of an electrode refers to the side of the electrode closest to the substrate during fabrication, while the opposite side, farther from the substrate, is the "top" or "upper" side.

[0085] In the present invention, substituted or unsubstituted C6-C 30Aryl refers to substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted substituted or unsubstituted triphenylene, substituted or unsubstituted perylenyl, substituted or unsubstituted indenyl, but not limited thereto.

[0086] In the present invention, substituted or unsubstituted C2-C 30 Heteroaryl refers to substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted The present invention also includes but is not limited to a substituted indolyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted benzoxazinyl, a substituted or unsubstituted benzothiazinyl, a substituted or unsubstituted acridinyl, a substituted or unsubstituted phenathiazinyl, a substituted or unsubstituted phenathiazinyl, a substituted or unsubstituted phenathiazinyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted carbazolyl, a combination thereof, or a fused ring of a combination of the foregoing groups, but is not limited thereto.

[0087] The C1-C of the present invention 10 Alkyl (including straight-chain alkyl and branched-chain alkyl) refers 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 is not limited thereto.

[0088] The C3-C 10A cycloalkyl group refers to a monovalent monocyclic saturated hydrocarbon group containing 3 to 10 carbon atoms as ring atoms. In this article, a C4-C9 cycloalkyl group is preferably used, a C5-C8 cycloalkyl group is more preferably used, and a C5-C7 cycloalkyl group is particularly preferably used. Non-limiting examples thereof include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

[0089] As the substrate for the organic electroluminescent device of the present invention, any substrate commonly used for 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 varying mechanical strength, thermal stability, transparency, surface smoothness, and water resistance. Depending on the properties of the substrate, its use varies. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0090] A first electrode is formed on a substrate, and the first electrode and the second electrode may be opposite to 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 metal mixture. The thickness of the first electrode layer depends on the material used, and is typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0091] 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.

[0092] Herein, the hole transport region constituting the organic electroluminescent device can be exemplified by a hole injection layer, a hole transport layer, an electron blocking layer, and the like.

[0093] As materials for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known materials used in OLED devices.

[0094] Examples of the above materials include phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinoline derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quilone derivatives, styrylanthracene derivatives, styrylamine derivatives and other styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylene vinyl and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and other conductive polymer oligomers, aromatic tertiary amine compounds, styrene amination compounds, compounds, triamines, tetraamines, benzidines, propargyl diamine derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1,1'-bis(4-diarylaminophenyl)cyclohexane, 4,4'-bis(diarylamino)biphenyls, bis[4-(diarylamino)phenyl]methanes, 4,4'-bis(diarylamino)terphenyls, 4,4'-bis(diarylamino)quaterphenyls, 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.

[0095] Furthermore, depending on the device configuration, the hole transport layer between the electron blocking and hole injection layers of the organic electroluminescent device can be a single layer or a stacked structure of multiple hole transport materials. In this document, the thickness of the various hole carrier conducting layers with different functions described above is not particularly limited.

[0096] The hole injection layer contains a host organic material that can conduct holes, and also contains a P-type dopant material with a deep HOMO energy level (the corresponding LUMO energy level will also be very deep). Based on empirical summary, in order to achieve smooth hole injection from the anode to the organic film layer, the HOMO energy level of the host organic material used in the anode interface buffer layer must have certain characteristics with the P-doped material. Only then can the charge transfer state between the host material and the dopant material be achieved, and ohmic contact between the buffer layer and the anode can be achieved, achieving efficient injection and conduction of holes from the electrode.

[0097] In view of the above empirical summary, for hole-type host materials with different HOMO energy levels, different P-doped materials need to be selected to match them in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0098] Therefore, in one embodiment of the present invention, in order to better inject holes, the hole injection layer further includes a P-type dopant material with charge conductivity selected from the following: quinone derivatives, such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives, such as 4,4',4"-((1E,1'E,1"E)-cyclopropane-1,2,3-trimethylenetris(cyanoformylidene))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0099] In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type doping material is 99:1-95:5, preferably 99:1-97:3, based on mass.

[0100] The thickness of the hole injection layer of the present invention may be 5-100 nm, preferably 5-50 nm, and more preferably 5-20 nm, but the thickness is not limited to this range.

[0101] The thickness of the hole transport layer of the present invention may be 5-200 nm, preferably 10-150 nm, and more preferably 20-100 nm, but the thickness is not limited to this range.

[0102] The thickness of the electron blocking layer of the present invention may be 1-50 nm, preferably 5-40 nm, but the thickness is not limited to this range.

[0103] After forming the hole injection layer, the hole transport layer and the electron blocking layer, a corresponding light emitting layer is formed on the electron blocking layer.

[0104] The light-emitting layer may include a host material and a dopant material. The host material may be a common green light host material in the art, and the dopant material may be a boron-containing organic compound represented by the general formula (1) of the present invention.

[0105] The light-emitting layer may contain a single host material or a dual host material;

[0106] The dual host material comprises a first host material and a second host material, wherein at least one of the first host material and the second host material is preferably a TADF material;

[0107] TADF materials exhibit thermally activated delayed fluorescence (TADF), characterized by a small energy difference between the first excited singlet and triplet states. This allows for simultaneous utilization of both singlet and triplet excitons within the device, resulting in a near 100% utilization rate of electrically generated excitons within the device. Compared to traditional fluorescent materials, TADF materials exhibit higher exciton utilization.

[0108] The light-emitting layer may comprise a host material, an exciton-sensitizing material, and a dopant material;

[0109] Exciton-sensitizing materials refer to materials that enable the luminescent material in the luminescent layer to fully utilize electroexcitons, thereby ultimately producing an emission spectrum of the sensitized material. Exciton sensitizers may perform functions such as exciton capture, exciton conversion, and exciton transfer in electroluminescent devices. The combination of the boron-containing organic compound containing a cyclohexanecarbazole ring represented by general formula (1) of the present invention and the exciton-sensitizing material significantly improves device efficiency, exciton annihilation in the device, and efficiency reduction.

[0110] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material used is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0111] The thickness of the light-emitting layer can be adjusted to optimize the luminous efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, and more preferably 15-40 nm, but the thickness is not limited to this range.

[0112] In the present 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.

[0113] The hole blocking layer is a layer that blocks holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the life of the device and improving the performance of the device. The hole blocking layer of the present invention can be arranged above the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds with hole blocking effects known in the prior art can be used, for example, phenanthroline derivatives such as bathocuproine (referred to as BCP), metal complexes of hydroxyquinoline derivatives such as aluminum (III) bis(2-methyl-8-quinolinol)-4-phenylphenolate (BAlq), various rare earth complexes, oxazole derivatives, triazole derivatives, triazine derivatives, pyrimidine derivatives such as 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 the present invention can be 2-200 nm, preferably 5-150 nm, but the thickness is not limited to this range.

[0114] The electron transport layer can be disposed on the light-emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that readily accepts electrons from the cathode and transfers the received electrons to the light-emitting layer. Preferably, the material has a high electron mobility. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials for organic electroluminescent devices known in the prior art can be used, for example, metal complexes of hydroxyquinoline derivatives represented by Alq3, BAlq and Liq, various rare earth metal complexes, triazole derivatives, 2,4-bis(9,9-dimethyl-9H-fluoren-2-yl)-6-(naphthalene-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6) and other triazine derivatives, 2-(4-(9,10-di(naphthalene-2-yl)anthracene-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole (CAS No.: 561064-11-7, commonly known as LG201) and other imidazole derivatives, 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 may be 10-80 nm, preferably 20-60 nm, and more preferably 25-45 nm, but the thickness is not limited to this range.

[0115] The electron injection layer may be provided above the electron transport layer. The electron injection layer material is generally preferably a material having a low work function so that electrons are easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, the electron injection layer materials for organic electroluminescent devices known in the prior art can be used, for example, lithium; lithium salts such as 8-hydroxyquinoline lithium, 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.

[0116] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or a compound or mixture thereof; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode may include, but is not limited to, Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or a compound or mixture thereof. The thickness of the cathode depends on the material used.

[0117] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign 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.

[0118] The method for preparing an organic electroluminescent device of the present invention comprises 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 cover layer, on a substrate. In this regard, vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI methods 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.

[0119] Synthesis Example

[0120] The raw materials involved in the synthesis examples of the present invention can be purchased from the market or prepared by conventional preparation methods in the art;

[0121] Example 1 Synthesis of Compound 58:

[0122]

[0123] Preparation of intermediate a1:

[0124] Under nitrogen protection, 2.01 g (10 mmol) of raw material A1, 3.38 g (10 mmol) of raw material B1, 1.68 g (15 mmol) of potassium tert-butoxide, 0.46 g (0.5 mmol) of Pd2(dba)3, 0.35 mL (1.5 mmol) of tri-tert-butylphosphine, and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 17 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a1. LC-MS: Measured value: 412.20 ([M+H] + ), theoretical value: 411.16.

[0125] Preparation of intermediate b1:

[0126] Under nitrogen, 4.11 g (10 mmol) of intermediate a1, 2.07 g (15 mmol) of potassium carbonate, 0.11 g (0.5 mmol) of palladium acetate, 0.44 g (1.5 mmol) of tri-tert-butylphosphine tetrafluoroborate, and 40 mL of DMAC were added to a three-necked flask and refluxed for 19 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b1. LC-MS: Measured value: 332.33 ([M+H] +), theoretical value: 331.23.

[0127] Preparation of intermediate c1:

[0128] In a three-necked flask, under nitrogen protection, 3.31 g (10 mmol) of intermediate b1, 1.87 g (10.5 mmol) of NBS, and 50 mL of dichloromethane were added and reacted at room temperature in the dark for 5 hours. The mixture was concentrated and purified by silica gel column chromatography to obtain intermediate c1. LC-MS: Measured value: 410.17 ([M+H] + ), theoretical value: 409.14.

[0129] Preparation of intermediate d1:

[0130] Under nitrogen protection, 4.1 g (10 mmol) of intermediate c1, 1.83 g (10 mmol) of raw material C1, 1.68 g (15 mmol) of potassium tert-butoxide, 0.46 g (0.5 mmol) of Pd2(dba)3, 0.35 mL (1.5 mmol) of tri-tert-butylphosphine, and 25 mL of anhydrous toluene were added to a three-necked flask and refluxed 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 d1. LC-MS: Measured value: 513.44 ([M+H] + ), theoretical value: 512.30.

[0131] Preparation of raw materials D1 and D2:

[0132] Under nitrogen protection, 5.12 g (10 mmol) of intermediate d1, 2.07 g (15 mmol) of potassium carbonate, 0.11 g (0.5 mmol) of palladium acetate, 0.44 g (1.5 mmol) of tri-tert-butylphosphine tetrafluoroborate, and 40 mL of DMAC were added to a three-necked flask and refluxed for 40 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain raw materials D1 and D2. Raw material D1: LC-MS: Measured value: 477.36 ([M+H] + ), theoretical value: 476.32; Raw material D2: LC-MS: measured value: 477.29 ([M+H] + ), theoretical value: 476.32.

[0133] Preparation of intermediate a-1:

[0134] Under nitrogen protection, 4.77 g (10 mmol) of raw material D2, 0.44 g (11 mmol) of NaH dissolved in mineral oil (60%), and 20 mL of anhydrous DMF were added to a three-necked flask and stirred at room temperature for 0.5 hours. 2.48 g (10 mmol) of raw material A-1 dissolved in 15 mL of anhydrous DMF was added dropwise and reacted at 100 degrees Celsius for 10 hours. After the reaction was completed, 50 mL of deionized water was added, the precipitate was filtered and dissolved in dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and filtered to collect. The organic layer was concentrated and then purified by silica gel column chromatography to obtain intermediate a-1. LC-MS: Measured value: 705.42 ([M+H] + ), theoretical value: 704.31.

[0135] Preparation of intermediate b-1:

[0136] Under nitrogen protection, 2.79g (10mmol) of raw material B-1, 0.44g (11mmol) of NaH dissolved in mineral oil (60%) and 20mL of anhydrous DMF were added to a three-necked flask and stirred at room temperature for 0.5 hours. 7.04g (10mmol) of intermediate a-1 dissolved in 25mL of anhydrous DMF was added dropwise and reacted at 100 degrees Celsius for 12 hours. After the reaction was completed, 50mL of deionized water was added, the precipitate was filtered and dissolved in dichloromethane, the organic phase was dried over anhydrous sodium sulfate, filtered and collected, and the organic layer was concentrated and then purified by silica gel column chromatography to obtain intermediate b-1. LC-MS: Measured value: 964.55 ([M+H] + ), theoretical value: 963.51.

[0137] Preparation of compound 58:

[0138] In a sealed pressure tube, under nitrogen protection, 9.6g (10mmol) of intermediate b-1 and 55mL of anhydrous o-dichlorobenzene were added dropwise. After cooling to -78°C, 4.8mL (12mmol) of 2.5M n-butyllithium-n-hexane solution was added dropwise. After transferring to 60°C for reaction for 2 hours, the reaction was cooled to -42°C and 1.44mL (15mmol) of boron tribromide was added dropwise. After slowly returning to room temperature and reacting for 2 hours, 2.58g (3.5mL, 20mmol) of ultra-dry N,N-diisopropylamide lithium was added dropwise under the condition of cooling to 0°C. The reaction solution was heated to 180°C for reaction for 12 hours. After cooling to room temperature, the low-boiling point solvent was removed by distillation under reduced pressure, dissolved in dichloromethane, filtered, dried over anhydrous sodium sulfate, and the filtrate was collected by filtration. The filtrate was concentrated and purified by column chromatography to obtain compound 58. Compound 58 was dissolved in toluene solution (1×10 -5 The half-peak width of M is 20 nm, which was measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0139] Example 2 Synthesis of Compound 162:

[0140]

[0141] Preparation of intermediate a-2:

[0142] Under nitrogen protection, 4.76g (10mmol) of raw material D2, 0.44g (11mmol) of NaH dissolved in mineral oil (60%), and 30mL of anhydrous DMF were added to a three-necked flask and stirred at room temperature for 0.5 hours. 2.67g (10mmol) of raw material A-2 dissolved in 25mL of anhydrous DMF was added dropwise and reacted at 100 degrees Celsius for 8 hours. After the reaction, 50mL of deionized water was added, the precipitate was filtered and dissolved in dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and filtered to collect. The organic layer was concentrated and then purified by silica gel column chromatography to obtain intermediate a-2. LC-MS: Measured value: 725.22 ([M+H] + ), theoretical value: 724.28.

[0143] Preparation of intermediate b-2:

[0144] Under nitrogen protection, 2.79 g (10 mmol) of raw material B-1, 0.44 g (11 mmol) of NaH dissolved in mineral oil (60%), and 50 mL of anhydrous DMF were added to a three-necked flask and stirred at room temperature for 0.5 hours. 7.24 g (10 mmol) of intermediate a-2 dissolved in 35 mL of anhydrous DMF was added dropwise and reacted at 100 degrees Celsius for 10 hours. After the reaction was completed, 50 mL of deionized water was added, the precipitate was filtered and dissolved in dichloromethane, the organic phase was dried over anhydrous sodium sulfate, filtered, and the organic layer was concentrated and then purified by silica gel column chromatography to obtain intermediate b-2. LC-MS: Measured value: 984.50 ([M+H] + ), theoretical value: 983.48.

[0145] Preparation of compound 162:

[0146] In a sealed pressure-resistant tube, under nitrogen protection, 9.8 g (10 mmol) of intermediate b-2 and 65 ml of o-dichlorobenzene were added. 4.8 mL (12 mmol) of 2.5 M n-butyl lithium in n-hexane solution was added at 0°C, heated to 60°C and reacted for 2 hours. Then, 1.44 mL (15 mmol) of boron tribromide was added at 0°C, and the reaction was continued at room temperature for 3 hours. Then, 2.58 g (3.5 mL, 20 mmol) of N,N-diisopropylethylamine was added to the system at 0°C, heated to 200°C and reacted for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 162. Compound 162 was dissolved in a toluene solution (1×10 -5 The half-peak width of M is 21 nm, which was measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0147] Example 3 Synthesis of Compound 174:

[0148]

[0149] Preparation of intermediate c-1:

[0150] Under nitrogen protection, 3.34 g (10 mmol) of raw material A-3, 40 mL of tetrahydrofuran, 5 mL of water, 0.23 g (0.2 mmol) of Pd(PPh3)4, and 1.38 g (10 mmol) of potassium carbonate were added to a three-necked flask and stirred under reflux for 5 hours. After cooling to room temperature, the organic phase was separated and collected, dried over anhydrous sodium sulfate, filtered, and concentrated. The organic phase was separated by column chromatography to obtain intermediate c-1. LC-MS: Measured value: 284.99 ([M+H] + ), theoretical value: 283.94.

[0151] Preparation of intermediate a-3:

[0152] Under nitrogen protection, 4.76g (10mmol) of raw material D1, 0.44g (11mmol) of NaH dissolved in mineral oil (60%), and 20mL of anhydrous DMF were added to a three-necked flask and stirred at room temperature for 0.5 hours. 2.84g (10mmol) of intermediate c-1 dissolved in 15mL of anhydrous DMF was added dropwise and reacted at 100 degrees Celsius for 12 hours. After the reaction was completed, 50mL of deionized water was added, the precipitate was filtered and dissolved in dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and filtered to collect. The organic layer was concentrated and then purified by silica gel column chromatography to obtain intermediate a-3. LC-MS: Measured value: 741.23 ([M+H] + ), theoretical value: 740.25.

[0153] Preparation of intermediate d-1:

[0154] Under nitrogen, 7.4 g (10 mmol) of intermediate a-3, 1.49 g (10 mmol) of raw material D-1, 1.68 g (15 mmol) of potassium tert-butoxide, 0.46 g (0.5 mmol) of Pd2(dba)3, 0.35 mL (1.5 mmol) of tri-tert-butylphosphine, and 50 mL of anhydrous toluene were added to a three-necked flask and refluxed for 13 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate d-1. LC-MS:

[0155] Measured value: 810.40 ([M+H] + ), theoretical value: 809.45.

[0156] Preparation of intermediate b-3:

[0157] Under nitrogen protection, 8.1 g (10 mmol) of intermediate d-1, 2.68 g (10 mmol) of raw material E-1, 1.68 g (15 mmol) of potassium tert-butoxide, 0.46 g (0.5 mmol) of Pd2(dba)3, 0.35 mL (1.5 mmol) of tri-tert-butylphosphine, and 55 mL of anhydrous toluene were added to a three-necked flask and refluxed for 19 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:

[0158] Measured value: 998.55 ([M+H] + ), theoretical value: 997.51.

[0159] Preparation of compound 174:

[0160] In a sealed pressure-resistant tube, under nitrogen protection, 10 g (10 mmol) of intermediate b-3 and 75 ml of o-dichlorobenzene were added. 4.8 mL (12 mmol) of 2.5 M tert-butyl lithium in n-hexane was added at 0°C, the system was heated to 60°C and reacted for 2 hours, then 1.44 mL (15 mmol) of boron tribromide was added at 0°C, the reaction was continued at room temperature for 2 hours, and then 2.58 g (3.5 mL, 20 mmol) of N,N-diisopropylethylamine was added to the system at 0°C, heated to 200°C and reacted for 15 hours. After the reaction was completed, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography to obtain compound 174. Compound 174 was dissolved in a toluene solution (1×10 -5 The half-peak width of M is 22 nm, which was measured by Horiba's Fluorolog-3 series fluorescence spectrometer. 1H NMR (400 MHz, deuterated chloroform): δ 1.24-1.87 (40H, m), 2.11-2.43 (10H, m), 6.66 (2H, dd), 7.18 (2H, dd), 7.40 (1H, dd), 7.51-7.79 (10H, m), 7.93-8.12 (4H, m), 8.99 (1H, dd).

[0161] Example 4 Synthesis of Compound 205:

[0162]

[0163] Preparation of intermediate a-4:

[0164] Under nitrogen protection, 4.76g (10mmol) of raw material D2, 0.44g (11mmol) of NaH dissolved in mineral oil (60%), and 40mL of anhydrous DMF were added to a three-necked flask and stirred at room temperature for 0.5 hours. 3.17g (10mmol) of raw material A-4 dissolved in 15mL of anhydrous DMF was added dropwise and reacted at 100 degrees Celsius for 10 hours. After the reaction was completed, 50mL of deionized water was added, the precipitate was filtered and dissolved in dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and filtered to collect. The organic layer was concentrated and then purified by silica gel column chromatography to obtain intermediate a-4. LC-MS: Measured value: 775.17 ([M+H] + ), theoretical value: 774.15.

[0165] Preparation of intermediate b-4:

[0166] In a three-necked flask, under nitrogen protection, 7.74 g (10 mmol) of intermediate a-4, 1.95 g (13 mmol) of raw material D-2, 4.89 g (15 mmol) of cesium carbonate, and 60 mL of anhydrous DMF were added and heated to 80°C for 16 hours. After cooling naturally to room temperature, 100 mL of water was added, and the precipitate was filtered and collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to obtain intermediate b-4. LC-MS: Measured value: 905.29 ([M+H] + ), theoretical value: 904.25.

[0167] Preparation of intermediate e-1:

[0168] In a sealed pressure-resistant tube, under nitrogen protection, 9 g (10 mmol) of intermediate b-4 and 65 ml of o-dichlorobenzene were added. 4.8 mL (12 mmol) of 2.5 M n-butyllithium in n-hexane was added at 0°C, the system was heated to 60°C and reacted for 2 hours, then 1.44 mL (15 mmol) of boron tribromide was added at 0°C, the reaction was continued at room temperature for 2 hours, and then 2.58 g (3.5 mL, 20 mmol) of N,N-diisopropylethylamine was added to the system at 0°C, heated to 180°C and reacted for 13 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-1. LC-MS: Measured value: 787.42 ([M+H] + ), theoretical value: 786.34.

[0169] Preparation of compound 205:

[0170] In a sealed pressure-resistant tube, under nitrogen protection, 7.86 g (10 mmol) of intermediate e-1, 45 ml of anhydrous DMF, and 1 g (12 mmol) of CuCN were added. The mixture was heated to 150 degrees Celsius for 18 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 205. Compound 205 was dissolved in a toluene solution (1×10 -5 The half-peak width of M is 19 nm, which was measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0171] Example 5 Synthesis of Compound 289:

[0172]

[0173] Preparation of intermediate c-2:

[0174] Under nitrogen protection, 3.17 g (10 mmol) of raw material A-5, 20 mL of tetrahydrofuran, 2 mL of water, 0.23 g (0.2 mmol) of Pd(PPh3)4, and 1.38 g (10 mmol) of potassium carbonate were added to a three-necked flask and stirred under reflux for 4 hours. After cooling to room temperature, the organic phase was separated and collected, dried over anhydrous sodium sulfate, and filtered. The organic phase was concentrated and separated by column chromatography to obtain intermediate c-2. LC-MS: Measured value: 381.17 ([M+H] + ), theoretical value: 380.10.

[0175] Preparation of intermediate a-5:

[0176] Under nitrogen protection, 4.76g (10mmol) of raw material D1, 0.44g (11mmol) of NaH dissolved in mineral oil (60%), and 30mL of anhydrous DMF were added to a three-necked flask and stirred at room temperature for 0.5 hours. 3.8g of intermediate c-2 dissolved in 25mL of anhydrous DMF was added dropwise and reacted at 100 degrees Celsius for 17 hours. After the reaction, 50mL of deionized water was added, the precipitate was filtered and dissolved in dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and filtered to collect. The organic layer was concentrated and then purified by silica gel column chromatography to obtain intermediate a-5. LC-MS: Measured value: 837.40 ([M+H] + ), theoretical value: 836.41.

[0177] Preparation of intermediate b-5:

[0178] Under nitrogen protection, 2.79 g (10 mmol) of raw material B-1, 0.44 g (11 mmol) of NaH dissolved in mineral oil (60%) and 20 mL of anhydrous DMF were added to a three-necked flask and stirred at room temperature for 0.5 hours. 8.36 g (10 mmol) of intermediate a-5 dissolved in 35 mL of anhydrous DMF was added dropwise and reacted at 100 degrees Celsius for 10 hours. After the reaction was completed, 50 mL of deionized water was added, the precipitate was filtered and dissolved in dichloromethane, the organic phase was dried over anhydrous sodium sulfate, filtered and collected, and the organic layer was concentrated and then purified by silica gel column chromatography to obtain intermediate b-5. LC-MS: Measured value: 1096.66 ([M+H] + ), theoretical value: 1095.60.

[0179] Preparation of compound 289:

[0180] In a sealed pressure-resistant tube, under nitrogen protection, 10 g (10 mmol) of intermediate b-5 and 65 ml of o-dichlorobenzene were added. 4.8 mL (12 mmol) of 2.5 M tert-butyl lithium in n-hexane was added at 0°C, the system was heated to 60°C and reacted for 3 hours, then 1.44 mL (15 mmol) of boron tribromide was added at 0°C, the reaction was continued at room temperature for 3 hours, and then 2.58 g (3.5 mL, 20 mmol) of N,N-diisopropylethylamine was added to the system at 0°C, heated to 200°C and reacted for 19 hours. After the reaction was completed, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography to obtain compound 289. Compound 289 was dissolved in a toluene solution (1×10 -5 The half-peak width of M is 22 nm, which was measured by Horiba's Fluorolog-3 series fluorescence spectrometer. 1H NMR (400 MHz, deuterated chloroform): δ 1.32-1.80 (58H, m), 2.11 (3H, s), 2.15-2.47 (7H, m), 7.15 (1H, dd), 7.36-7.61 (5H, m), 7.79 (1H, dd), 7.82-8.11 (7H, m), 8.27 (1H, d), 8.91 (1H, dd).

[0181] Example 6 Synthesis of Compound 366:

[0182]

[0183] Preparation of intermediate b-6:

[0184] In a three-necked flask, under nitrogen protection, 7.04 g (10 mmol) of intermediate a-1, 3.39 g (13 mmol) of raw material D-3, 4.88 g (15 mmol) of cesium carbonate, and 80 mL of anhydrous DMF were added and heated to 100°C for 24 hours. The mixture was naturally cooled to room temperature, 100 mL of water was added, and the precipitate was filtered and collected. The precipitate was dissolved in 50 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to obtain intermediate b-6. LC-MS: Measured value: 946.36 ([M+H] + ), theoretical value: 945.42.

[0185] Preparation of compound 366:

[0186] In a sealed pressure-resistant tube, under nitrogen protection, 9.45 g (10 mmol) of intermediate b-6 and 75 ml of o-dichlorobenzene were added. 4.8 mL (12 mmol) of 2.5 M n-butyl lithium in n-hexane solution was added at 0°C, the system was heated to 60°C and reacted for 2 hours, then 1.44 mL (15 mmol) of boron tribromide was added at 0°C, the reaction was continued at room temperature for 4 hours, and then 2.58 g (3.5 mL, 20 mmol) of N,N-diisopropylethylamine was added to the system at 0°C, heated to 200°C and reacted for 10 hours. After the reaction was completed, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography to obtain compound 366. Compound 366 was dissolved in a toluene solution (1×10 -5 The half-peak width of M is 18 nm, which was measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0187] Example 7 Synthesis of Compound 382:

[0188]

[0189] Preparation of intermediate a-6:

[0190] Under nitrogen protection, 4.76g (10mmol) of raw material D2, 0.44g (11mmol) of NaH dissolved in mineral oil (60%) and 35mL of anhydrous DMF were added to a three-necked flask and stirred at room temperature for 0.5 hours. 2.84g (10mmol) of intermediate c-1 dissolved in 15mL of anhydrous DMF was added dropwise and reacted at 100 degrees Celsius for 14 hours. After the reaction was completed, 50mL of deionized water was added, the precipitate was filtered and dissolved in dichloromethane, and the organic phase was dried over anhydrous sodium sulfate and filtered to collect. The organic layer was concentrated and then purified by silica gel column chromatography to obtain intermediate a-6. LC-MS: Measured value: 741.28 ([M+H] + ), theoretical value: 740.25.

[0191] Preparation of intermediate d-2:

[0192] Under nitrogen protection, 7.40 g (10 mmol) of intermediate a-6, 1.49 g (10 mmol) of raw material D-4, 1.68 g (15 mmol) of potassium tert-butoxide, 0.46 g (0.5 mmol) of Pd2(dba)3, 0.35 mL (1.5 mmol) of tri-tert-butylphosphine, and 55 mL of anhydrous toluene were added to a three-necked flask and refluxed 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 d-2. LC-MS:

[0193] Measured value: 810.49 ([M+H] + ), theoretical value: 809.45.

[0194] Preparation of intermediate b-7:

[0195] Under nitrogen protection, 8.1 g (10 mmol) of intermediate d-2, 3.23 g (10 mmol) of raw material D-5, 1.68 g (15 mmol) of potassium tert-butoxide, 0.46 g (0.5 mmol) of Pd2(dba)3, 0.35 mL (1.5 mmol) of tri-tert-butylphosphine, and 60 mL of anhydrous toluene were added to a three-necked flask and refluxed for 17 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-7. LC-MS:

[0196] Measured value: 1053.61 ([M+H] + ), theoretical value: 1052.55.

[0197] Preparation of compound 382:

[0198] In a sealed pressure-resistant tube, under nitrogen protection, 10 g (10 mmol) of intermediate b-7 and 80 ml of o-dichlorobenzene were added. 4.8 mL (12 mmol) of 2.5 M tert-butyl lithium in n-hexane solution was added at 0°C, the system was heated to 60°C and reacted for 2 hours, then 1.44 mL (15 mmol) of boron tribromide was added at 0°C, the reaction was continued at room temperature for 3 hours, and then 2.58 g (3.5 mL, 20 mmol) of N,N-diisopropylethylamine was added to the system at 0°C, heated to 200°C and reacted for 19 hours. After the reaction was completed, the organic layer was reduced in pressure and concentrated, and then purified by silica gel column chromatography to obtain compound 382. Compound 382 was dissolved in a toluene solution (1×10 -5 The half-peak width of M is 18 nm, which was measured by Horiba's Fluorolog-3 series fluorescence spectrometer. 1 H NMR (400 MHz, deuterated chloroform): δ 1.35 (9H, s), 1.41-1.82 (22H, m), 2.11-2.37 (10H, m), 6.68 (2H, dd), 6.82-7.23 (9H, m), 7.26-8.01 (18H, m), 8.36 (1H, dd).

[0199] The structural characteristics of the compounds obtained in each example are shown in Table 1

[0200] Table 1

[0201]

[0202] The following describes in detail the application effects of the OLED materials synthesized by the present invention in devices using device Examples 1-7 and Comparative Examples 1-3. The device manufacturing processes for Device Examples 2-7 and Comparative Examples 1-3 are identical to those of Device Example 1, and the same substrate and electrode materials are used, with the same electrode material thickness. The only difference is that the light-emitting layer material in the device is replaced. The layer structures and test results of each device example are shown in Tables 2-1 and 3, respectively:

[0203] Device Example 1

[0204] like Figure 1As shown, the transparent substrate layer 1 is a transparent PI film, and the ITO anode layer 2 (film thickness of 150nm) is washed, that is, washed with a detergent (Semiclean M-L20), washed with pure water, dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, a vacuum evaporation device is used to evaporate HT-1 and HI-1 with a film thickness of 10nm as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60nm is evaporated as the hole transport layer 4. Then, EB-1 with a thickness of 30nm is evaporated as the electron blocking layer 5. After the above-mentioned electron blocking material evaporation is completed, the light-emitting layer 6 of the OLED light-emitting device is prepared, using GH-1 and GH-2 as the main materials, compound 58 as the doping material, the mass ratio of GH-1, GH-2 and compound 58 is 69:30:1, and the light-emitting layer thickness is 30nm. After the light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm. This layer served as the hole-blocking layer 7. After the hole-blocking layer 7, ET-1 and Liq were vacuum-deposited in a 1:1 weight ratio to form a 30 nm thick film. This served as the electron-transporting layer 8. On the electron-transporting layer 8, a 1 nm thick LiF layer was vacuum-deposited. This served as the electron-injection layer 9. On the electron-injection layer 9, an 80 nm thick Mg:Ag electrode layer was vacuum-deposited in a 1:9 weight ratio. This served as the cathode layer 10.

[0205] The following describes in detail the effects of using the OLED materials synthesized by the present invention in devices using device Examples 8-14 and Comparative Examples 4-6. The device fabrication processes for Device Examples 9-14 and Comparative Examples 4-6 are identical to those of Device Example 8, and the same substrate and electrode materials are used, with the same electrode thickness. The only difference is that the light-emitting layer material in the device is replaced. The layer structures and test results for each device example are shown in Tables 2-2 and 3, respectively:

[0206] Device Example 8

[0207] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness 150nm) is washed, i.e., washed with a detergent (Semiclean M-L20), washed with pure water, dried, and then subjected to UV-ozone cleaning to remove organic residues from the transparent ITO surface. On the washed ITO anode layer 2, a 10nm thick layer of HT-1 and HI-1 is deposited using a vacuum evaporation device as the hole injection layer 3. The mass ratio of HT-1 to HI-1 is 97:3. HT-1 is then evaporated to a thickness of 60nm as the hole transport layer 4. EB-1 is then evaporated to a thickness of 30nm as the electron blocking layer 5. After the electron-blocking material deposition was completed, the light-emitting layer 6 of the OLED light-emitting device was formed. GH-1 and GH-2 were used as the host materials, GD-1 was used as the first dopant material, and Compound 58 was used as the second dopant material. The mass ratio of GH-1, GH-2, GD-1, and Compound 58 was 66:30:3:1, and the light-emitting layer had a thickness of 30 nm. Following the light-emitting layer 6, HB-1 was vacuum-deposited to a thickness of 5 nm. This layer served as the hole-blocking layer 7. Following the hole-blocking layer 7, ET-1 and Liq were vacuum-deposited to a thickness of 30 nm. The electron-transporting layer 8 was formed by vacuum deposition of ET-1 and Liq in a mass ratio of 1:1. A 1 nm thick LiF layer was deposited on the electron-transporting layer 8 using a vacuum deposition apparatus. This layer served as the electron-injection layer 9. An 80 nm thick Mg:Ag electrode layer was deposited on the electron-injection layer 9 using a vacuum deposition apparatus. The mass ratio of Mg:Ag was 1:9. This layer served as the cathode layer 10.

[0208] The molecular structure formula of the relevant materials is shown below:

[0209]

[0210]

[0211] After completing the OLED light-emitting device as described above, the anode and cathode were connected using a known drive circuit, and the device's current efficiency, external quantum efficiency, and lifetime were measured. Examples and comparative examples 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 resulting devices are shown in Table 3.

[0212] Table 2-1

[0213]

[0214] Table 2-2

[0215]

[0216] Table 3

[0217]

[0218]

[0219] Note: Current efficiency and luminescence peak were measured using an IVL (current-voltage-luminance) test system (Suzhou Fushida Scientific Instrument Co., Ltd.); the lifespan test system was an EAS-62C OLED device lifespan tester from Japan System Giken Co., Ltd.; LT95 refers to the time it takes for the device's luminance to decay to 95%; all data are measured at 10 mA / cm 2 Next test.

[0220] The device data results in Table 3 show that, compared with the comparative compounds ref-1, ref-2, and ref-3, the compounds of the present invention have emission peaks between 510 and 550 nm, and are capable of achieving a good green emission effect. Compared with device comparative examples 1-6, the organic light-emitting devices of the present invention, whether in a single-doping system or a dual-doping system, have significantly improved current efficiency and lifespan compared to OLED devices using known materials. When an exciton-sensitizing material is used as the first dopant, the device efficiency is significantly improved compared to the single-doping system.

[0221] In summary, the above are only preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principles of the present invention should be included in the scope of protection of the present invention.

Claims

1. A boron-containing organic compound containing cyclohexanecarbazole ring, characterized in that: The structures of the boron-containing organic compounds are shown in general formula (1) and general formula (2): In the general formula (1) and the general formula (2), R1-R 11 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, phenyl substituted amino, tert-butylbenzene substituted amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; Ar1 and Ar2 are independently represented by one of hydrogen atom, deuterium atom, methyl group and CD3; M1 represents one of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted benzofuranyl, and substituted or unsubstituted benzothiophenyl; X represents one of O, S, and N (Q1); Q1 is independently substituted or unsubstituted C3 to C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; The substituents for the substituent group are selected from deuterium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

2. A boron-containing organic compound containing cyclohexanecarbazole ring, characterized in that: The structure of the boron-containing organic compound is shown in any one of the general formulas (3) to (6): In general formula (3) to general formula (6), R1-R 11 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, phenyl substituted amino, tert-butylbenzene substituted amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; Ar1 and Ar2 are independently represented by one of hydrogen atom, deuterium atom, methyl group and CD3; X represents one of O, S, and N (Q1); Q1 is independently substituted or unsubstituted C3 to C 10 Cycloalkyl, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; Y is represented by one of O and S; R 12 -R 15 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, phenyl substituted amino, tert-butylbenzene substituted amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; The substituents for the substituent group are selected from deuterium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

3. A boron-containing organic compound containing cyclohexanecarbazole ring, characterized in that: The structure of the boron-containing organic compound is shown in any one of general formulas (7) to (10): In general formula (7) to general formula (10), R1-R 11 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, phenyl substituted amino, tert-butylbenzene substituted amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; Ar1 and Ar2 are independently represented by one of hydrogen atom, deuterium atom, methyl group and CD3; R 12 -R 18 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, phenyl substituted amino, tert-butylbenzene substituted amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; The substituents for the substituent group are selected from deuterium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

4. The boron-containing organic compound containing cyclohexanecarbazole ring according to claim 2, characterized in that: The structure of the boron-containing organic compound is shown in any one of general formulas (11) to (14): In general formula (11) to general formula (14), X, R1-R 11 has the same meaning as defined in claim 2; Y is represented by one of O and S; R 12 -R 15 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, phenyl substituted amino, tert-butylbenzene substituted amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; The substituents for the substituent group are selected from deuterium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

5. A boron-containing organic compound containing cyclohexanecarbazole ring, characterized in that: The structure of the boron-containing organic compound is shown in any one of general formulas (15) to (38): In general formulas (15) to (38), R2, R5, R6, R9, R 10 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, phenyl substituted amino, tert-butylbenzene substituted amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 Each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 Alkyl, substituted or unsubstituted C3~C 10 Cycloalkyl, substituted or unsubstituted C1~C 10 Alkoxy, phenyl substituted amino, tert-butylbenzene substituted amino, substituted or unsubstituted C6~C 30 Aryl, substituted or unsubstituted C2~C 30 One of the heteroaryl groups; The substituents for the substituent group are selected from deuterium atoms, halogen atoms, cyano groups, C1-C 10 Alkyl, C3~C 10 Cycloalkyl, C6~C 30 Aryl, C2~C 30 one or more of heteroaryl groups; The heteroatom in the heteroaryl group is selected from one of O, S, N, Si and B.

6. The boron-containing organic compound containing cyclohexanecarbazole ring according to claim 1, characterized in that: R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 、R 11 They are independently represented as follows: Hydrogen atom, cyano group, Any of the following; The M1 is represented by any one of the following ring structures: The Z is represented by CR a ; R a Each occurrence independently represents one of a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, and a spirofluorenyl group.

7. The boron-containing organic compound containing cyclohexanecarbazole ring according to claim 2 or 4, characterized in that: R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 、R 11 、R 12 、R 13 、R 14 、R 15 They are independently represented as follows: Hydrogen atom, cyano group, Any one of them.

8. The boron-containing organic compound containing cyclohexanecarbazole ring according to claim 3, characterized in that: R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 They are independently represented as follows: Hydrogen atom, cyano group, Any one of them.

9. The boron-containing organic compound containing cyclohexanecarbazole ring according to claim 5, characterized in that: R2, R5, R6, R9, R 10 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 They are independently represented as follows: Hydrogen atom, cyano group, Any one of them.

10. The boron-containing organic compound containing cyclohexanecarbazole ring according to claim 1, characterized in that: R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 、R 11 Each independently represents a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group , isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted 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, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, methoxy, tert-butoxy; The M1 represents one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, benzofuranyl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, and tert-butyl-substituted biphenyl; The substituents for the substituent group are optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthrenyl group.

11. The boron-containing organic compound containing cyclohexanecarbazolyl ring according to claim 2 or 4, characterized in that: R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 、R 11 、R 12 、R 13 、R 14 、R 15 Each independently represents a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group , isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted 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, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, methoxy, tert-butoxy; The substituents for the substituent group are optionally selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-amyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolyl group, an isoquinolyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothienyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, and an azaphenanthrenyl group.

12. The boron-containing organic compound containing cyclohexanecarbazole ring according to claim 3, characterized in that: R1, R2, R3, R4, R5, R6, R7, R8, R9, R 10 、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 Each independently represents a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group , isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted 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, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, methoxy, tert-butoxy.

13. The boron-containing organic compound containing cyclohexanecarbazole ring according to claim 5, characterized in that: R2, R5, R6, R9, R 10 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 Each independently represents a hydrogen atom, a deuterium atom, a cyano group, a halogen atom, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolyl group, a furyl group, a thienyl group, a benzofuranyl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorenyl group, a methyl-substituted phenyl group, an ethyl-substituted phenyl group , isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted 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, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthone, phenyl-substituted triazinyl, methoxy, tert-butoxy.

14. A boron-containing organic compound containing a cyclohexanecarbazole ring, characterized in that: The specific structure of the boron-containing organic compound is any one of the following structures:

15. An organic electroluminescent device comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, wherein the organic light-emitting functional layer comprises a light-emitting layer, characterized in that: The light-emitting layer contains the boron-containing organic compound containing cyclohexanecarbazolyl ring according to any one of claims 1 to 14. 16 . The organic electroluminescent device according to claim 15 , wherein the light-emitting layer comprises a host material and a dopant material, and the dopant material comprises the boron-containing organic compound containing cyclohexanecarbazolyl ring according to claim 1 .

17. The organic electroluminescent device according to claim 15, wherein the light-emitting layer comprises a first host material, a second host material and a dopant material, at least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-containing organic compound containing cyclohexanecarbazole ring according to any one of claims 1 to 14.

18. The organic electroluminescent device according to claim 15, wherein the light-emitting layer comprises a host material, an exciton-sensitizing material, and a doping material, wherein: The exciton-sensitizing material is a complex containing a metal element, and the doping material is the boron-containing organic compound containing a cyclohexanecarbazole ring according to any one of claims 1 to 14.

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