A boron-containing organic compound and use thereof

Abstract

The application relates to a boron-containing organic compound and application thereof, and belongs to the technical field of semiconductors. The structure of the compound is shown in general formula (1). The compound has a narrow half-peak width and a high fluorescence quantum yield. When the compound is used as a doping material in a light-emitting layer material of an OLED light-emitting device, the current efficiency of the device is remarkably improved, and the light-emitting color purity and the device life are also greatly improved.

Description

[0001] The present application is based on the prior application No. 202211391057.X, the application date is November 8, 2022, and the invention name is: a kind of boron-containing organic compound and its application. TECHNICAL FIELD

[0002] The present application relates to the field of semiconductor technology, in particular to a kind of boron-containing organic compound and its application. BACKGROUND

[0003] Traditional fluorescent dopant material is limited to early technology, only 25% singlet exciton formed by electric excitation can be utilized to form light, the internal quantum efficiency of device is low (the highest is 25%), and the external quantum efficiency is generally less than 5%, which is far from the efficiency of phosphorescent device. Phosphorescent material can effectively utilize singlet exciton and triplet exciton formed by electric excitation to form light due to the strong spin-orbit coupling of heavy atom center, so that the internal quantum efficiency of device reaches 100%.

[0004] With the coming of 5G era, higher requirements are put forward for color rendering standard. In addition to high efficiency and stability, luminescent material also needs narrower half peak width to improve the color purity of device light-emitting. Fluorescent dopant material can realize high fluorescence quantum and narrow half peak width through molecular engineering. Blue fluorescent dopant material has achieved a phased breakthrough, and the half peak width of boron-based material can be reduced to below 30 nm. However, the research on green light region which is more sensitive to human eye mainly focuses on phosphorescent dopant material, but it is difficult to narrow the light-emitting peak shape through simple method. Therefore, in order to meet higher color rendering standard, it is of great significance to study high-efficiency green fluorescent dopant material with narrow half peak width.

[0005] In addition, sensitization technology combines triplet exciton sensitization material with fluorescent dopant material, uses triplet exciton sensitization material as exciton sensitization medium, fully utilizes triplet exciton, and transfers energy to fluorescent dopant material through energy transfer, which can also achieve 100% internal quantum efficiency of device. This technology can make up for the shortcomings of insufficient utilization rate of fluorescent dopant material exciton, effectively play the characteristics of high fluorescence quantum yield, high device stability, high color purity and low cost of fluorescent dopant material, and has broad prospects in OLEDs application.

[0006] Boron compounds with resonant structures are more likely to achieve narrow half-width emission (HWHM). When applied to sensitized fluorescence technology, 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 technology using TADF materials with a minimum singlet and triplet energy level difference of less than or equal to 0.2 eV as the main body and boron-containing materials as dopants; CN 110492005 A and CN 110492009 A disclose a light-emitting layer combination scheme using exciton complexes as the main body and boron-containing materials as dopants; both achieve efficiencies comparable to phosphorescence and relatively narrow HWHM. Therefore, developing sensitization technology based on narrow HWHM boron-based light-emitting materials has unique advantages and strong potential for achieving BT.2020 display performance. Summary of the Invention

[0007] In view of the above-mentioned problems in the prior art, the applicant of this invention provides a boron-containing organic compound and its application. The boron-containing organic compound of this invention can be used as a green light doping material for the light-emitting layer of organic electroluminescent devices, thereby improving the purity of the emitted color and the lifetime of the device.

[0008] The technical solution of the present invention is as follows: a boron-containing organic compound, the structure of which is shown in general formula (1):

[0009]

[0010] In general formula (1), M1 and M2 represent substituted or unsubstituted C6-C. 30 Aromatic ring, substituted or unsubstituted C3-C 30 Mixed aromatic rings;

[0011] Ar1 refers to C1 to C1, whether substituted or unsubstituted. 10 Alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0012] Ar1 and M1 can be connected to form a ring;

[0013] Z represents CH or CR. a The R a Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or substituted or unsubstituted C1-C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C4-C10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; adjacent R a They can be connected to form a ring;

[0014] R1 and R2 represent hydrogen atoms, substituted or unsubstituted C1 to C2 atoms, respectively. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C4-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; R1 and R2 can be linked to form a ring;

[0015] The substituents of the above-mentioned substituted groups may be selected from halogen atoms, deuterium atoms, cyano groups, C1-C groups. 10 Alkyl, C5-C 10 cycloalkyl, 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;

[0016] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0017] In a preferred embodiment, the structure of the boron-containing organic compound is shown in any one of general formulas (1-1) to (1-3):

[0018]

[0019] In general formulas (1-1) to (1-3), the definitions of Z, M1, M2, and Ar1 are the same as those in the above description.

[0020] In a preferred embodiment, the structure of the boron-containing organic compound is shown in any one of general formulas (1-4) to (1-9):

[0021]

[0022]

[0023] In general formulas (1-4) to (1-9), the definitions of Z, M1, M2, and Ar1 are the same as those in the above description;

[0024] Z1, Z2, and Z3 are each independently represented as CH or CR. b ;R b Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or substituted or unsubstituted C1-C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C4-C 10 Aryloxy group, substituted or unsubstituted aromatic amino group, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; adjacent R b They can be connected to form a ring;

[0025] The substituents of the above-mentioned substituted groups may be selected from halogen atoms, deuterium atoms, cyano groups, C1-C groups. 10 Alkyl, C5-C 10 Cycloalkenyl, C1-C 10 alkoxy groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups;

[0026] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0027] In a preferred embodiment, the structure of the boron-containing organic compound is shown in general formula (2):

[0028]

[0029] In general formula (2), the definitions of Z, Z1, Z2, Z3, M1, R1, R2, and Ar1 are the same as those in the above description.

[0030] In a preferred embodiment, the structure of the boron-containing organic compound is shown in any one of general formulas (2-1) to (2-6):

[0031]

[0032] In general formulas (2-1) to (2-6), the definitions of Z, M2, R1, R2, and Ar1 are the same as those in the above description;

[0033] R3 and R4 represent hydrogen atoms, substituted or unsubstituted C1-C atoms. 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0034] X is represented as C(R5)(R6), Si(R7)(R8), N(R9), O, S;

[0035] The recurrence of R5, R6, R7, and R8, whether identical or different, indicates the presence of H, deuterium, or substituted or unsubstituted C1-C atoms. 10 Alkyl or silyl, substituted or unsubstituted C2-C 10 alkenyl, substituted amino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0036] R9 indicates substituted or unsubstituted C1-C. 10 Alkyl or silyl, substituted or unsubstituted C2-C 10 alkenyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups;

[0037] The substituents of the above-mentioned substituted groups may be selected from halogen atoms, deuterium atoms, cyano groups, C1-C groups. 10 Alkyl, C5-C 10 Cycloalkenyl, C1-C 10 alkoxy groups, C3-C 10 cycloalkyl, C6-C 30 Aryl, C3-C 30 One or more of the heteroaryl groups;

[0038] The heteroatom in the heteroaryl group is selected from one of O, S, N, and Si.

[0039] In a preferred embodiment, the structure of the boron-containing organic compound is shown in any one of general formulas (2-7) to (2-12):

[0040]

[0041]

[0042] In general formulas (2-7) to (2-12), the definitions of Z, Z1, Z2, Z3, X, R1, R2, R3, R4, and Ar1 are the same as those in the above description.

[0043] In a preferred embodiment, the structure of the boron-containing organic compound is shown in any one of general formulas (2-13) to (2-17):

[0044]

[0045] In general formulas (2-13) to (2-17), the definitions of Z, Z1, Z2, Z3, X, R3, and R4 are the same as those in the above description.

[0046] In a preferred embodiment, M1 is represented by any of the following ring structures:

[0047]

[0048]

[0049] M2 can be represented by any of the following ring structures:

[0050]

[0051] The definition of Z is the same as the limitation mentioned above.

[0052] In a preferred embodiment, R1 and R2 represent the same or different hydrogen atoms, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, or substituted or unsubstituted furan. Substituent or unsubstituted thiophene group, substituted or unsubstituted benzofuran group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted N-phenylcarbazolyl group, substituted or unsubstituted dimethylfluorenyl group, substituted or unsubstituted diphenylfluorenyl group, substituted or unsubstituted spirofluorenyl group, substituted or unsubstituted amino group, substituted or unsubstituted triazine group, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole;

[0053] The R a R bThe following are represented as identical or different deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted methyl groups, substituted or unsubstituted ethyl groups, substituted or unsubstituted isopropyl groups, substituted or unsubstituted tert-butyl groups, substituted or unsubstituted cyclohexyl groups, substituted or unsubstituted adamantyl groups, substituted or unsubstituted phenyl groups, substituted or unsubstituted diphenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthracene groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted pyridyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted furanyl groups, etc. Substituted or unsubstituted thiophene group, substituted or unsubstituted benzofuran group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted N-phenylcarbazolyl group, substituted or unsubstituted dimethylfluorenyl group, substituted or unsubstituted diphenylfluorenyl group, substituted or unsubstituted spirofluorenyl group, substituted or unsubstituted amino group, substituted or unsubstituted triazine group, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole;

[0054] Ar1 is represented as adamantyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted vinyl, substituted or unsubstituted propenyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthryl, or substituted or unsubstituted pyridine. alkyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiopheneyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiopheneyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiopheneyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino;

[0055] M1 and M2 are independently represented as one of the following: substituted or unsubstituted phenyl, naphthyl, anthraceneyl, phenanthryl, pyridyl, quinolinyl, furanyl, thiophene, benzofuranyl, benzothiophene, dibenzofuranyl, dibenzothiophene, carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted indole[3,2,1-jk]carbazoyl, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazoyl;

[0056] The substituents of the aforementioned substituted groups are independently represented as one or more of the following: deuterium atom, fluorine atom, adamantyl, methyl, ethyl, isopropyl, cyclopentyl, tert-butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthryl, cyano, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthryl.

[0057] In a preferred embodiment, R5, R6, R7, and R8 represent the same or different hydrogen atoms, substituted or unsubstituted methyl groups, substituted or unsubstituted ethyl groups, substituted or unsubstituted isopropyl groups, substituted or unsubstituted tert-butyl groups, substituted or unsubstituted cyclohexyl groups, substituted or unsubstituted adamantyl groups, substituted or unsubstituted phenyl groups, substituted or unsubstituted diphenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthracene groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted pyridyl groups, substituted or unsubstituted quinolinyl groups, and substituted or unsubstituted... Furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted amino, substituted or unsubstituted triazine, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole;

[0058] R3, R4, and R9 represent the same or different substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, etc. Substituted or unsubstituted thiophene group, substituted or unsubstituted benzofuran group, substituted or unsubstituted benzothiophene group, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted dibenzothiophene group, substituted or unsubstituted carbazolyl group, substituted or unsubstituted N-phenylcarbazolyl group, substituted or unsubstituted dimethylfluorenyl group, substituted or unsubstituted diphenylfluorenyl group, substituted or unsubstituted spirofluorenyl group, substituted or unsubstituted amino group, substituted or unsubstituted triazine group, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole;

[0059] The substituents of the aforementioned substituted groups are independently represented as one or more of the following: deuterium atom, fluorine atom, adamantyl, methyl, ethyl, isopropyl, cyclopentyl, tert-butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthryl, cyano, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthryl.

[0060] In a preferred embodiment, the R a R b It can be represented as the structure shown below:

[0061]

[0062] Any one of them; the Ar1 is represented by the following structure:

[0063]

[0064] Any one of them.

[0065] In a preferred embodiment, the boron-containing organic compound has a specific structural formula of any one of the following:

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074] A preferred organic light-emitting device includes a substrate, a cathode, an anode, and a functional layer located between the cathode and the anode, wherein the functional layer comprises any one of the boron-containing organic compounds described above.

[0075] Preferably, the functional layer includes a light-emitting layer, which comprises a host material and a dopant material, wherein the dopant material is any of the boron-containing organic compounds described in the present invention.

[0076] Preferably, 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 any one of the boron-containing organic compounds described herein.

[0077] Preferably, 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 any one of the boron-containing organic compounds described above.

[0078] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0079] (1) The compound of the present invention can be used as a doping material for OLED devices, and can emit fluorescence under the action of an electric field. It can be applied to OLED lighting or OLED display fields.

[0080] (2) The compound of the present invention is used as a doping material, and phosphorescent material is introduced as an exciton sensitizer, which can effectively improve the device lifetime;

[0081] (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;

[0082] The compounds of this invention have narrow half-widths and can be used as doping materials for the light-emitting layer of organic electroluminescent devices, thereby improving the purity of the emitted color and the lifetime of the device. Attached Figure Description

[0083] Figure 1 This is a schematic diagram of the structure of an OLED device in which the materials listed in this invention are applied;

[0084] 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

[0085] The present invention will now be described in detail with reference to the accompanying drawings and embodiments.

[0086] 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.

[0087] In this invention, C6-C is substituted or unsubstituted. 30 Aryl groups refer to substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthraquinyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted dimethylfluorenyl groups, substituted or unsubstituted diphenylfluorenyl groups, substituted or unsubstituted spirofluorenyl groups, substituted or unsubstituted phenanthrene groups, substituted or unsubstituted tetraphenyl groups, substituted or unsubstituted pyrene groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted para-triphenyl groups, substituted or unsubstituted meta-triphenyl groups, and substituted or unsubstituted phenyl groups. The compounds may be substituted, substituted or unsubstituted triphenyl, substituted or unsubstituted peryl, substituted or unsubstituted indole, but are not limited thereto.

[0088] In this invention, C3-C is substituted or unsubstituted. 30 Heteroaryl refers to 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... The fused ring of substituted 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 phenthiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fumonyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoleyl, combinations thereof, or combinations of the foregoing groups, but not limited thereto.

[0089] 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.

[0090] The C3-C of this invention 10Cycloalkyl 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.

[0091] 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.

[0092] 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.

[0093] 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.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] 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.

[0098] 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.

[0099] 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.

[0100] 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.

[0101] 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.

[0102] 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.

[0103] 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.

[0104] 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.

[0105] 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.

[0106] 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.

[0107] The light-emitting layer can contain a single-substrate material or a dual-substrate material;

[0108] 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;

[0109] 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.

[0110] The light-emitting layer may include a host material, an exciton-sensitizing material, and a dopant material;

[0111] 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.

[0112] 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.

[0113] 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.

[0114] 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.

[0115] 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.

[0116] 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.

[0117] 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.

[0118] The second electrode may be disposed above the electron transport region. The second electrode may be a cathode. The second electrode may be a transmission electrode, a semi-transmission electrode, or a reflection electrode. When the second electrode is a transmission electrode, it may include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or compounds or mixtures thereof; when the second electrode is a semi-transmission electrode or a reflection electrode, it may include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or compounds or mixtures thereof, but is not limited thereto. The thickness of the cathode depends on the material used.

[0119] 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.

[0120] 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.

[0121] Synthesis Examples

[0122] All raw materials involved in the synthesis embodiments of this invention can be purchased from the market or obtained by conventional preparation methods in the art.

[0123] Synthesis of Compounds in Examples

[0124] Example 1: Synthesis of Compound 28:

[0125]

[0126] Preparation of intermediate R1:

[0127] Under nitrogen protection, 12 mmol of starter B1 and 100 mL of anhydrous N,N-dimethylformamide were added to a dry three-necked flask. Then, 14 mmol of NaH coated with mineral oil (65%) was added in portions under ice-water bath conditions. The mixture was stirred for 0.6 hours, and then 10 mmol of starter A1 solution dissolved in 21 mL of anhydrous DMF was slowly added dropwise. After the reaction was complete, 150 mL of water was added to quench the reaction. A large amount of precipitate was obtained by filtration, dried and filtered with dichloromethane solution and anhydrous sodium sulfate. The filtrate was rotary evaporated until no fraction remained. The precipitate was purified by silica gel column chromatography using petroleum ether as the developing solvent to obtain intermediate R1. LC-MS: Measured value: 506.01 ([M+H)) + Theoretical value: 505.08.

[0128] Preparation of intermediate S1:

[0129] Under nitrogen protection, 10 mmol of starting material C1 and 100 mL of anhydrous N,N-dimethylformamide were added to a dry three-necked flask. Mineral oil-coated (65%) NaH (net content 11 mmol) was added in portions under ice-water bath conditions. The mixture was stirred for 0.45 hours, and then 10 mmol of intermediate R1 solution dissolved in 21 mL of anhydrous DMF was slowly added dropwise. After the reaction was complete, 150 mL of water was added to quench the reaction. A large amount of precipitate was obtained by filtration, dried and filtered with dichloromethane solution and anhydrous sodium sulfate. The filtrate was rotary evaporated until no fraction remained. Purification was performed using petroleum ether as the developing solvent via silica gel column chromatography to obtain intermediate S1. LC-MS: Measured value: 818.15 ([M+H)) + Theoretical value: 817.21.

[0130] Preparation of compound 28:

[0131] In a dry three-necked flask, 6 mmol of intermediate S1 and 45 mL of tert-butylbenzene were added. The mixture was cooled to -78 °C, and 6.8 mmol of a n-butyllithium solution in n-hexane was slowly added. The mixture was then stirred and brought to room temperature, then heated to 60 °C, and the n-hexane was removed under negative pressure. The reaction was carried out under nitrogen protection for 2 hours. At -41 °C, 6 mmol of BBr3 was added, and the reaction was maintained at this temperature for 2 hours. The mixture was then slowly restored to room temperature and stirred at room temperature for 12 hours. Subsequently, 10 mmol of DIPEA (N,N-diisopropylethylamine) was added under ice-water bath conditions, and the mixture was heated to 120 °C and refluxed for 36 hours. After the reaction was complete, the mixture was cooled to room temperature, filtered through diatomaceous earth, and the organic phase was collected. The high-boiling solvent was removed by vacuum distillation, dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, and the organic phase was concentrated. The organic phase was purified by silica gel column chromatography using toluene as the developing solvent to obtain compound 28. The half-peak width (WHM) in the toluene solution (1 × 10⁻⁵ M) was 22 nm.

[0132] Example 2: Synthesis of compound 112:

[0133]

[0134] Preparation of intermediate Y1:

[0135] Under nitrogen protection, 12 mmol of raw material E1 and 100 mL of anhydrous tetrahydrofuran were added to a dry three-necked flask. The mixture was cooled to -78 °C, and 10.6 mmol of n-butyllithium solution was slowly added dropwise. The reaction was maintained at this temperature for 2 h. Then, 10 mmol of raw material D1 was added dropwise to this solution at a constant rate. After the addition was complete, the resulting mixture was gradually heated to room temperature and quenched with 200 mL of saturated NaHCO3 aqueous solution. The mixture was extracted with dichloromethane, the organic layer was dried over magnesium sulfate, filtered, and the high-boiling solvent was removed by vacuum distillation. The crude residue was placed in a clean flask and dissolved in 25 mL of acetic acid solution. Then, 30 mL of 5 mol% HCl aqueous solution was added, and the entire solution mixture was refluxed for 11 h. After cooling to room temperature, the intermediate Y1 was purified by silica gel column chromatography using dichloromethane / n-hexane as the developing solvent. LC-MS: 332.21 ([M+H)) + Theoretical value: 331.14.

[0136] Preparation of intermediate R2:

[0137] Intermediate R2 was synthesized using the same method as intermediate R1, except that intermediate Y1 was used to replace starting material B1. LC-MS analysis showed a value of 504.11 ([M+H)). + Theoretical value: 503.07.

[0138] Preparation of intermediate S2:

[0139] The synthesis of intermediate S2 is based on intermediate S1, except that starting material C2 replaces starting material C1, and intermediate R2 replaces intermediate R1, yielding intermediate S2. LC-MS: Measured value: 803.11 ([M+H)). + Theoretical value: 802.20.

[0140] Preparation of compound 112:

[0141] The synthesis of compound 112 is based on compound 28, except that intermediate S1 is replaced by intermediate S2 to obtain compound 112. In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 23 nm.

[0142] Example 3: Synthesis of Compound 125:

[0143]

[0144] Preparation of intermediate Y1:

[0145] The synthesis method of intermediate Y1 is the same as described in Example 2.

[0146] Preparation of intermediate T1:

[0147] Under nitrogen protection, in a dry three-necked flask, 69 mmol of starting material F1, 85 mmol of starting material G1, 41 mmol of sodium tert-butoxide, 0.34 mmol of Pd2(dba)3, 0.2 mol of tri-tert-butylphosphine, and 250 mL of toluene were added. After the addition was complete, the mixture was heated to reflux and reacted for 10 hours. After the reaction was completed, the reaction solution was diluted with 200 mL of ethyl acetate, then washed successively with water, saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate = 50:1) to give intermediate T1. LC-MS: Measured value: 447.12 ([M+H) + Theoretical value: 446.27.

[0148] Preparation of intermediate R2:

[0149] The synthesis method of intermediate R2 is the same as that described in Example 2.

[0150] Preparation of intermediate S3:

[0151] The synthesis of intermediate S3 referenced intermediate S2, except that intermediate T1 was used to replace starting material C2, yielding intermediate S3. LC-MS: Measured value: 930.06 ([M+H)). + Theoretical value: 929.33.

[0152] Preparation of compound 125:

[0153] The synthesis of compound 125 is based on compound 28, except that intermediate S1 is replaced by intermediate S3, yielding compound 125. In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 25 nm.

[0154] Example 4: Synthesis of Compound 142:

[0155]

[0156] Preparation of intermediate Y1:

[0157] The synthesis method of intermediate Y1 is the same as described in Example 2.

[0158] Preparation of intermediate R2:

[0159] The synthesis method of intermediate R2 is the same as that described in Example 2.

[0160] Preparation of intermediate S4:

[0161] The synthesis of intermediate S4 referenced intermediate S2, except that starting material C3 was used instead of starting material C2 to obtain intermediate S4. LC-MS: Measured value: 816.16 ([M+H)). +Theoretical value: 815.19.

[0162] Preparation of compound 142:

[0163] The synthesis of compound 142 is based on compound 28, except that intermediate S1 is replaced by intermediate S4, yielding compound 142. In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 22 nm.

[0164] Example 5: Synthesis of Compound 143:

[0165]

[0166] Preparation of intermediate Y1:

[0167] The synthesis method of intermediate Y1 is the same as described in Example 2.

[0168] Preparation of intermediate R2:

[0169] The synthesis method of intermediate R2 is the same as that described in Example 2.

[0170] Preparation of intermediate S5:

[0171] Intermediate S5 was synthesized from intermediate S2, except that starting material C1 was used instead of starting material C2 to obtain intermediate S5. LC-MS: Measured value: 816.07 ([M+H)). + Theoretical value: 815.19.

[0172] Preparation of compound 143:

[0173] The synthesis of compound 143 is based on compound 28, except that intermediate S1 is replaced by intermediate S5, yielding compound 143. In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 24 nm.

[0174] Example 6: Synthesis of Compound 189:

[0175]

[0176] Preparation of intermediate Y1:

[0177] The synthesis method of intermediate Y1 is the same as described in Example 2.

[0178] Preparation of intermediate R3:

[0179] In a dry round-bottom flask, 22 mmol of intermediate Y1, 27 mmol of NaH, and 50 mL of DMF were added. After stirring at room temperature for 0.5 hours, 10 mmol of starting material A2 was added to the reaction mixture, and the mixture was stirred at 140 °C for 12 hours. After cooling to room temperature, the mixture was filtered, and the solid was washed with DMF. The residue was dissolved in tetrahydrofuran, and the insoluble matter was filtered off and evaporated under reduced pressure to give intermediate R3.

[0180] LC-MS: Measured value: 893.13 ([M+H]) + Theoretical value: 892.11.

[0181] Preparation of intermediate S6:

[0182] In a dry round-bottom flask equipped with a magnetic stirrer, under nitrogen atmosphere, a hexane solution of n-butyllithium (3.1 mL, 2.5 M, 5 mmol) was slowly added to 100 mL of toluene solution as intermediate R3. After stirring for 1 hour, the reaction mixture was cooled to -40 °C. 4 mmol of boron tribromide was added, and the reaction mixture was stirred at room temperature for 1 hour. 10 mmol of N,N-diisopropylethylamine was added at 0 °C, and the reaction mixture was then heated to 120 °C. After stirring for 8 hours, the reaction mixture was cooled to room temperature. The solution was filtered, washed with dichloromethane, and the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether:dichloromethane = 20:1) and recrystallized from dichloromethane and methanol to give intermediate S6. LC-MS: Measured value: 823.16 ([M+H)). + Theoretical value: 822.18.

[0183] Preparation of compound 189:

[0184] In a dry round-bottom flask equipped with a magnetic stirrer, under a nitrogen atmosphere, 5.5 mmol of a hexane solution of n-butanol was slowly added to a solution of 5 mmol of intermediate S6 in 120 mL of THF. After stirring for 1 hour, 7.5 mmol of dimethylmalononitrile was added, and the reaction mixture was allowed to slowly rise to room temperature. After stirring at room temperature for 8 hours, the solution was filtered, washed with dichloromethane, the filtrate was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether: dichloromethane = 5:1) and recrystallized from dichloromethane to give compound 189. (1 × 10⁻⁶) -5 The half-width at half maximum (WHM) is 27 nm.

[0185] Example 7: Synthesis of compound 213:

[0186]

[0187] Preparation of intermediate R4:

[0188] Intermediate R4 was synthesized using the same method as intermediate R1, except that starting material B2 was used instead of starting material B1. LC-MS analysis showed a value of 382.11 ([M+H)). + Theoretical value: 381.05.

[0189] Preparation of intermediate S7:

[0190] Intermediate S7 was synthesized from intermediate S2, except that intermediate R4 was used instead of intermediate R2 to obtain intermediate S7. LC-MS: Measured value: 681.13 ([M+H)). + Theoretical value: 680.18.

[0191] Preparation of compound 213:

[0192] The synthesis of compound 213 is based on compound 28, except that intermediate S1 is replaced by intermediate S7, yielding compound 213. In toluene solution (1×10⁻⁶) -5 The half-width at half maximum (WHM) is 26 nm.

[0193] Note: Half-width at half-maximum (FWHM) was measured using a Horiba Fluorolog-3 series fluorescence spectrometer.

[0194] The structural characterization of the compounds obtained in each embodiment is shown in Table 1.

[0195] Table 1

[0196]

[0197] The compounds of this invention can be used as doping materials for the light-emitting layer in light-emitting devices.

[0198] Device Examples

[0199] The application effects of the OLED materials synthesized in this invention in devices are described in detail below through device examples 1-7 and device comparative examples 1-2. The fabrication processes of device examples 2-7 and device comparative examples 1-2 are completely identical to those of device example 1, and the same substrate and electrode materials are used, with the electrode film thickness remaining consistent. The only difference is the replacement of the light-emitting layer material in the device. The layer structures and test results of each device example are shown in Tables 2 and 3, respectively.

[0200] Device Example 1

[0201] like Figure 1As 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 28 as the dopant material, with a mass ratio of GH-1, GH-2, and compound 28 of 69:30:1, and 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.

[0202] The application effects of the OLED materials synthesized in this invention in devices are described in detail below through device examples 8-14 and device comparative examples 3-4. The fabrication processes of device examples 9-14 and device comparative examples 3-4 are completely identical to those of device example 8, and the same substrate and electrode materials are used, with the electrode film thickness remaining consistent. The only difference is the replacement of the light-emitting layer material in the device. The layer structures and test results of each device example are shown in Tables 2 and 3, respectively.

[0203] Device Example 8

[0204] 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. Finally, a 30nm thick layer of EB-1 is deposited as an electron blocking layer 5. After the electron blocking material is deposited, the emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as the host materials, GD-1 is used as the first dopant, and compound 28 is used as the second dopant. The mass ratio of GH-1, GH-2, GD-1, and compound 28 is 66:30:3:1, and the thickness of the emitting layer is 30 nm. After the emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer is the hole blocking layer 7. After the hole blocking layer 7, ET-1 and Liq are vacuum-deposited to a mass ratio of 1:1; the thickness of this layer is 30 nm; this layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a thickness of 1 nm is fabricated using a vacuum evaporation apparatus; this layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a thickness of 80 nm is fabricated using a vacuum evaporation apparatus; the mass ratio of Mg to Ag is 1:9; this layer is used as the cathode layer 10.

[0205] The molecular structural formulas of the relevant materials are shown below:

[0206]

[0207]

[0208] 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 and lifetime of the device are measured. Examples and comparative examples of devices prepared using the same method are shown in Table 2; the test results for the current efficiency and lifetime of the obtained devices are shown in Table 3.

[0209] Table 2

[0210]

[0211]

[0212] Table 3

[0213]

[0214] Note: Current efficiency and emission peak were measured using an IVL (current-voltage-brightness) testing system (Suzhou Fushida Scientific Instruments Co., Ltd.); the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Inc., Japan; LT95 refers to the time it takes for the device brightness to decay to 95%; all data are within 10 mA / cm². 2 Next test.

[0215] As can be seen from the device data results in Table 3, compared with the devices in Comparative Examples 1-4, the organic light-emitting devices of the present invention achieve significant improvements in current efficiency and lifetime compared with OLED devices made of known materials, whether in a single-doped or double-doped system; when using an exciton-sensitized material as the first dopant, the device efficiency is significantly improved compared with that in the single-doped system.

[0216] In summary, the above are merely preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A boron-containing organic compound, characterized in that, The structure of the boron-containing organic compound is shown in general formula (1-8): In general formula (1-8), M1 represents any of the following ring structures: Ar1 refers to substituted or unsubstituted C3-C. 10 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; Z represents CH or CR. a The R a Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or substituted or unsubstituted C1-C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; Z1, Z2, and Z3 are each independently represented as CH or CR. b ;R b Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or substituted or unsubstituted C1-C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; The substituents of the above-mentioned substituted groups may be selected from halogen atoms, deuterium atoms, cyano groups, C1-C groups. 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. The boron-containing organic compound according to claim 1, characterized in that, The structure of the boron-containing organic compound is shown in general formula (1-9): In general formulas (1-9), the definition of Ar1 is the same as that in claim 1; M2 is represented by the following ring structure: Z represents CH or CR. a The R a Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or C1 to C2 atoms. 10 Alkyl, C3-C 10 cycloalkyl, C1-C 10 Alkoxy, C6~C 30 Aryl, C3~C 30 One of the heteroaryl groups; The substituents of the above-mentioned substituted groups may be selected from halogen atoms, deuterium atoms, cyano groups, C1-C groups. 10 Alkyl, C1-C 10 alkoxy groups, C3-C 10 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, said boron-containing organic compound having the structure shown in any one of general formulas (2-7) to (2-8): In general formulas (2-7) to (2-8), Z represents CH or CR. a The R a Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or substituted or unsubstituted C1-C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; Z1, Z2, and Z3 are each independently represented as CH or CR. b ;R b Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or substituted or unsubstituted C1-C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; R1 and R2 represent one of substituted or unsubstituted methyl and substituted or unsubstituted phenyl, respectively; R3 and R4 represent hydrogen atoms, substituted or unsubstituted C1-C atoms. 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; X is represented as N(R9), O, S; R9 indicates substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; The substituents of the above-mentioned substituted groups may be selected from halogen atoms, deuterium atoms, cyano groups, C1-C groups. 10 Alkyl, C1-C 10 alkoxy groups, C3-C 10 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. A boron-containing organic compound, said boron-containing organic compound having the structure shown in any one of general formulas (2-13) to (2-17): In general formulas (2-13) to (2-17), Z represents CH or CR. a The R a Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or substituted or unsubstituted C1-C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; Z1, Z2, and Z3 are each independently represented as CH or CR. b ;R b Each instance of the same or different element is represented by a deuterium atom, a halogen atom, a cyano group, or substituted or unsubstituted C1-C2 atoms. 10 Alkyl, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Alkoxy, substituted or unsubstituted C6-C 30 Aryl, substituted or unsubstituted C3-C 30 One of the heteroaryl groups; R3 and R4 represent hydrogen atoms, substituted or unsubstituted C1-C atoms. 10 Alkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; X is represented as N(R9), O, S; R9 indicates substituted or unsubstituted C6-C. 30 aryl, substituted or unsubstituted C3-C 30 heteroaryl groups; The substituents of the above-mentioned substituted groups may be selected from halogen atoms, deuterium atoms, cyano groups, C1-C groups. 10 Alkyl, C1-C 10 alkoxy groups, C3-C 10 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 1, characterized in that, The R a R b The following are represented as identical or different deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted methyl groups, substituted or unsubstituted ethyl groups, substituted or unsubstituted isopropyl groups, substituted or unsubstituted tert-butyl groups, substituted or unsubstituted cyclohexyl groups, substituted or unsubstituted adamantyl groups, substituted or unsubstituted phenyl groups, substituted or unsubstituted diphenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthracene groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted pyridyl groups, substituted or unsubstituted quinolinyl groups, and substituted or unsubstituted hydroxyl groups. Furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; Ar1 represents adamantyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl; The substituents of the aforementioned substituted groups are independently represented as one or more of the following: deuterium atom, fluorine atom, adamantyl, methyl, ethyl, isopropyl, cyclopentyl, tert-butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthryl, cyano, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthryl.

6. The boron-containing organic compound according to claim 2, characterized in that, The R a The following are represented as identical or different deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted methyl groups, substituted or unsubstituted ethyl groups, substituted or unsubstituted isopropyl groups, substituted or unsubstituted tert-butyl groups, substituted or unsubstituted cyclohexyl groups, substituted or unsubstituted adamantyl groups, substituted or unsubstituted phenyl groups, substituted or unsubstituted diphenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthracene groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted pyridyl groups, substituted or unsubstituted quinolinyl groups, and substituted or unsubstituted hydroxyl groups. Furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; Ar1 represents adamantyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted isopropyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted phenyl, substituted or unsubstituted diphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl; The substituents of the aforementioned substituted groups are independently represented as one or more of the following: deuterium atom, fluorine atom, adamantyl, methyl, ethyl, isopropyl, cyclopentyl, tert-butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthryl, cyano, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthryl.

7. The boron-containing organic compound according to any one of claims 3-4, characterized in that, The R a R b The following are represented as identical or different deuterium atoms, halogen atoms, cyano groups, substituted or unsubstituted methyl groups, substituted or unsubstituted ethyl groups, substituted or unsubstituted isopropyl groups, substituted or unsubstituted tert-butyl groups, substituted or unsubstituted cyclohexyl groups, substituted or unsubstituted adamantyl groups, substituted or unsubstituted phenyl groups, substituted or unsubstituted diphenyl groups, substituted or unsubstituted terphenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthracene groups, substituted or unsubstituted phenanthryl groups, substituted or unsubstituted pyridyl groups, substituted or unsubstituted quinolinyl groups, and substituted or unsubstituted hydroxyl groups. Furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothiophenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl, substituted or unsubstituted N-phenylcarbazoyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted triazineyl, substituted or unsubstituted 4a,9a-dimethyl-9-phenyl-1,2,3,4-tetrahydrocarbazole; The substituents of the aforementioned substituted groups are independently represented as one or more of the following: deuterium atom, fluorine atom, adamantyl, methyl, ethyl, isopropyl, cyclopentyl, tert-butyl, methoxy, phenyl, diphenyl, naphthyl, anthracene, phenanthryl, cyano, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furanyl, thiopheneyl, indolyl, pyrroleyl, dibenzofuranyl, dibenzothiapheneyl, dimethylfluorenyl, spirofluorenyl, carbazoleyl, N-phenylcarbazoleyl, carbazolinyl, and azirphenanthryl.

8. The boron-containing organic compound according to claim 1, characterized in that, The R a R b It can be represented as the structure shown below: Any one of them; The Ar1 is represented by the following structure: Any one of them.

9. The boron-containing organic compound according to claim 2, characterized in that, The R a It can be represented as the structure shown below: Any one of them; the Ar1 is represented by the following structure: Any one of them.

10. The boron-containing organic compound according to claim 3 or 4, characterized in that, The R a R b It can be represented as the structure shown below: Any one of them.

11. The boron-containing organic compound according to any one of claims 1-4, characterized in that, The substituted or unsubstituted C6-C 30 Aryl groups refer to substituted or unsubstituted phenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted anthraquinyl groups, substituted or unsubstituted fluorenyl groups, substituted or unsubstituted dimethylfluorenyl groups, substituted or unsubstituted diphenylfluorenyl groups, substituted or unsubstituted spirofluorenyl groups, substituted or unsubstituted phenanthrene groups, substituted or unsubstituted tetraphenyl groups, substituted or unsubstituted pyrene groups, substituted or unsubstituted biphenyl groups, substituted or unsubstituted para-triphenyl groups, substituted or unsubstituted meta-triphenyl groups, and substituted or unsubstituted phenyl groups. alkyl, substituted or unsubstituted triphenylene, substituted or unsubstituted perylene, substituted or unsubstituted indole; The substituted or unsubstituted C3-C 30 Heteroaryl refers to 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, and substituted or unsubstituted benzene. Imidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted naphthinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridineyl, substituted or unsubstituted benzazinyl, substituted or unsubstituted benzathiazinyl, substituted or unsubstituted benzazinyl, substituted or unsubstituted fumonyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazoyl; The C1-C 10 Alkyl groups 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, and 1-butylpentyl. The C3-C 10 Cycloalkyl refers to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl.

12. A boron-containing organic compound, characterized in that, The boron-containing organic compound has a specific structural formula of any of the following:

13. An organic light-emitting device, comprising a substrate, a cathode, an anode, and a functional layer located between the cathode and the anode, characterized in that, The functional layer includes a light-emitting layer, which comprises a host material and a dopant material, wherein the dopant material is a boron-containing organic compound as described in any one of claims 1-12.

14. The organic light-emitting device according to claim 13, characterized in that, The light-emitting layer comprises a first host material, a second host material, and a dopant material, wherein at least one of the first host material and the second host material is a TADF material, and the dopant material is a boron-containing organic compound as described in any one of claims 1-12.

15. The organic light-emitting device according to claim 13, 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 1-12.

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