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

Abstract

The present invention discloses a boron-containing organic compound and an organic electroluminescent device prepared therefrom, belonging to the field of semiconductor technology. The structure of the organic compound of the present invention is shown in general formula (1). The compound of the present invention has a narrow full width at half maximum and can be used as a green light doping material for the light-emitting layer of an organic electroluminescent device, thereby improving the color purity and lifespan of the device.

Description

Technical Field

[0001] The present invention relates to the field of semiconductor technology, and particularly to a boron-containing organic compound as an OLED doping material and an organic electroluminescent device comprising the same. Background Art

[0002] Traditional fluorescent doping materials are limited by early technologies and can only utilize 25% of the singlet excitons formed by electrical excitation for luminescence. The internal quantum efficiency of the device is relatively low (up to 25%), and the external quantum efficiency is generally lower than 5%, showing a significant gap compared with the efficiency of phosphorescent devices. Phosphorescent materials, due to the strong spin-orbit coupling of heavy atom centers that enhances intersystem crossing, can effectively utilize both singlet excitons and triplet excitons formed by electrical excitation for luminescence, enabling the internal quantum efficiency of the device to reach 100%. However, most phosphorescent materials are expensive, with poor material stability, poor color purity, and serious device efficiency roll-off, which limit their application in OLEDs.

[0003] With the advent of the 5G era, higher requirements are put forward for the color rendering standard. In addition to being efficient and stable, the luminescent material also requires a narrower full width at half maximum to improve the color purity of device luminescence. Fluorescent doping materials can achieve high fluorescence quantum yield and narrow full width at half maximum through molecular engineering. Breakthroughs have been achieved in blue fluorescent doping materials, and the full width at half maximum of boron-based materials can be reduced to less than 30 nm. In the green light region, which is more sensitive to the human eye, research mainly focuses on phosphorescent doping materials, but it is difficult to narrow their emission peak shape through simple methods. Therefore, to meet higher color rendering standards, it is of great significance to study highly efficient green fluorescent doping materials with narrow full width at half maximum.

[0004] In addition, the sensitization technology combines a triplet exciton sensitizing material with a fluorescent doping material. Using the triplet exciton sensitizing material as an exciton sensitization medium, it fully utilizes triplet excitons and transfers the energy to the fluorescent doping material through energy transfer, which can also achieve a 100% internal quantum efficiency of the device. This technology can make up for the deficiency of the exciton utilization rate of fluorescent doping materials and effectively exert the characteristics of high fluorescence quantum yield, high device stability, high color purity, and low cost of fluorescent doping materials, showing broad prospects in the application of OLEDs.

[0005] Boron-based compounds with resonance structures are more likely to achieve narrow full-width at half-maximum (FWHM) luminescence. When such materials are applied in sensitization technologies, devices with high efficiency and narrow FWHM emission can be fabricated. For example, in CN 107507921 A and CN 110492006 A, a luminescent layer combination technology is disclosed, which uses a thermally activated delayed fluorescence (TADF) material with a lowest singlet-triplet energy difference less than or equal to 0.2 eV as the host and a boron-based material as the dopant; in CN 110492005 A and CN 110492009 A, a luminescent layer combination scheme is disclosed, which uses an exciplex as the host and a boron-based material as the dopant. Both can achieve efficiency comparable to that of phosphorescence and a relatively narrow FWHM. Therefore, developing sensitization technologies based on narrow FWHM boron-based luminescent materials has unique advantages and strong potential for meeting the BT.2020 display standards. Summary of the Invention

[0006] In view of the above problems existing in the prior art, the present invention provides a boron-containing organic compound and an organic electroluminescent device prepared therefrom. The compound of the present invention has a narrow FWHM and can be used as a green light dopant material for the luminescent layer of an organic electroluminescent device, thereby improving the color purity and lifespan of the device.

[0007] The technical solution of the present invention is as follows: A boron-containing organic compound, the structure of the boron-containing organic compound is shown in General Formula (1) and General Formula (2):

[0008]

[0009] In General Formula (1) and General Formula (2), each occurrence of Z is the same or different and represents C-R1 or N, and at least one Z represents N;

[0010] Each occurrence of Z1 is the same or different and represents C-R3;

[0011] Each occurrence of Z2 is the same or different and represents C-R4;

[0012] X1 and X2 each independently represent O, S, N(R5), C(R6)(R7), or Si(R8)(R9);

[0013] Each occurrence of R1, R3, and R4 is the same or different and represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C30 one of heteroaryl groups; adjacent R1s can be connected to each other to form a ring, adjacent R3s can be connected to each other to form a ring, and adjacent R4s can be connected to each other to form a ring;

[0014] Each occurrence of R5 is the same or different and represents a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 one of heteroaryl groups;

[0015] R6, R7, R8, and R9 are each independently a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 one of heteroaryl groups;

[0016] The substituents for the substituent groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a C2-C 30 heteroaryl group, an amino group, or one or more of them;

[0017] The heteroatoms in the heteroaryl groups are each independently selected from one or more of oxygen, sulfur, nitrogen, and silicon atoms.

[0018] Preferably, the structure of the organic compound is represented by General Formula (II-1) to General Formula (II-10):

[0019]

[0020]

[0021] In General Formula (II-1) to General Formula (II-10), the meanings of Z, Z1, Z2, R5, R6, R7, R8, and R9 are the same as defined above.

[0022] Preferably, the structure of the organic compound is any one of General Formula (HI-1) to General Formula (HI-4):

[0023]

[0024]

[0025] In General Formulas (III-1) to (III-4), the meanings of Z, Z1, Z2, X1, and X2 are the same as those defined above.

[0026] Preferably, the structure of the organic compound is any one of General Formulas (IV-1) to (IV-6):

[0027]

[0028] In General Formulas (IV-1) to (IV-6), the meanings of Z, Z1, Z2, X1, and X2 are the same as those defined above; each occurrence of Z3 is the same or different and represents C-R;

[0029] Each occurrence of R is the same or different and represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0030] The substituents for the substituent groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a C2-C 30 heteroaryl group, an amino group, or one or more of them;

[0031] The heteroatoms in the heteroaryl group are each independently selected from one or more of oxygen, sulfur, nitrogen, and silicon atoms.

[0032] Preferably, the structure of the organic compound is any one of General Formulas (V-1) and (V-2):

[0033]

[0034] In General Formulas (V-1) and (V-2), the meanings of Z1, Z2, X1, X2, and R1 are the same as those defined above;

[0035] Each occurrence of Z4, Z5, and Z6 is independently N or C-H;

[0036] R a 、 R b 、 R c 、 R d 、 R e 、 R f Each occurrence being the same or different represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0037] The substituents for the substituent groups are each independently selected from a deuterium atom, a halogen atom, a cyano group, a C1-C 10 alkyl group, a C3-C 10 cycloalkyl group, a C6-C 30 aryl group, a C2-C 30 heteroaryl group, an amino group, or a combination thereof;

[0038] The heteroatoms in the heteroaryl group are each independently selected from one or more of oxygen, sulfur, nitrogen, and silicon atoms.

[0039] Preferably, the R1, R3, R4, R, R a 、 R b 、 R c 、 R d 、 R e 、 R fThey are respectively represented by one of a hydrogen atom, a deuterium atom, a tritium atom, 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 phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a terphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene 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, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an xanthone group, a phenyl-substituted triazine group, a phenyl-substituted boranyl group, a methoxy group, a tert-butoxy group.

[0040] R2 and R5 each represent one of a hydrogen atom, a deuterium atom, a tritium atom, 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 phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a terphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene 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, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an xanthone group, a phenyl-substituted triazine group, a phenyl-substituted borane group, a methoxy group, a tert-butoxy group.

[0041] R6, R7, R8, and R9 are each independently represented by 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 phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a terphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a phenyl-substituted pyridyl group, a quinolinyl group, a furyl group, a thienyl group, a benzofuryl group, a dibenzofuryl group, a dibenzothienyl group, a carbazolyl group, an N-phenylcarbazolyl group, a 9,9-dimethylfluorenyl group, a spirofluorene 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, a deuterated methyl-substituted phenyl group, a deuterated ethyl-substituted phenyl group, a deuterated isopropyl-substituted phenyl group, a deuterated tert-butyl-substituted phenyl group, a deuterated methyl-substituted biphenyl group, a deuterated ethyl-substituted biphenyl group, a deuterated isopropyl-substituted biphenyl group, a deuterated tert-butyl-substituted biphenyl group, a tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl, an xanthenone group, a phenyl-substituted triazinyl group, a phenyl-substituted boranyl group, a methoxy group, or a tert-butoxy group.

[0042] Preferably, R, R1, R3, R4, Ra, R b , R c , R d , R e , R f are represented by the following structures:

[0043]

[0044] Preferably, the specific structural formula of the organic compound is any one of the following structures:

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062] An organic electroluminescent device includes a cathode and an anode, and an organic light-emitting functional layer therebetween. The organic light-emitting functional layer includes a light-emitting layer, and the light-emitting layer contains the boron-containing organic compound.

[0063] In a preferred embodiment, the light-emitting layer contains a host material and a doping material, and the doping material contains the boron-containing organic compound.

[0064] In a preferred embodiment, the light-emitting layer contains 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.

[0065] In a preferred embodiment, the light-emitting layer contains a host material, an exciton sensitizing material and a doping material. The exciton sensitizing material is a metal element-containing complex, and the doping material is the boron-containing organic compound.

[0066] The beneficial technical effects of the present invention are as follows:

[0067] (1) The compound of the present invention can be used as a doping material for the light-emitting layer material in an OLED device, and can emit green fluorescence under the action of an electric field, and can be applied to the fields of OLED lighting or OLED display; (2) As a doping material, the compound of the present invention introduces a phosphorescent material as an exciton sensitizer, which can effectively improve the device life;

[0068] (3) The spectral FWHM of the compound of the present invention is relatively narrow, which can effectively improve the device color gamut and the device luminous efficiency. Description of the Drawings

[0069] Figure 1 Schematic structural diagram of the materials listed in the present invention applied to an OLED device;

[0070] 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 implementation manners

[0071] Next, the technical solutions in the embodiments of the present invention will be clearly and completely described in conjunction with the accompanying drawings in the embodiments of the present invention. Without conflict, the embodiments and features in the embodiments of the present invention can be combined with each other. The present invention will be further described below in conjunction with the accompanying drawings and specific embodiments, but it is not a limitation of the present invention.

[0072] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, the orientation words such as "upper", "lower", "top", and "bottom" only represent the orientation in a certain specific state, and do not mean that the relevant structures can only exist in the described orientation; on the contrary, if the structure can be transformed in position, for example, inverted, the orientation of the structure will be changed accordingly. Specifically, in the present invention, the "bottom" and "lower" sides of the electrode refer to the side of the electrode close to the substrate during the preparation process, and the opposite side away from the substrate is the "top" and "upper" sides.

[0073] In the present invention, substituted or unsubstituted C6-C 30 aryl and / or substituted or unsubstituted C2-C 30Heteroaryl refers to substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted condensed tetraphenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted p-terphenyl, substituted or unsubstituted m-terphenyl, substituted or unsubstituted group, substituted or unsubstituted meta-terphenyl, substituted or unsubstituted perylenyl, substituted or unsubstituted indenyl, 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 benzofuryl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzimidazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazinyl, substituted or unsubstituted benzothiazinyl, substituted or unsubstituted acridinyl, substituted or unsubstituted phenazinyl, substituted or unsubstituted phenothiazinyl, substituted or unsubstituted phenoxazinyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl, their combinations or fused rings of the foregoing group combinations, but not limited thereto.

[0074] The C1-C 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 not limited thereto.

[0075] The halogen atom in the present invention refers to a chlorine atom, a fluorine atom, a bromine atom, etc., but not limited thereto.

[0076] The C3-C 10 Cycloalkyl refers to a monovalent monocyclic saturated hydrocarbon group including 3 to 10 carbon atoms as ring-forming atoms. In this article, C4-C9 cycloalkyl is preferably used, more preferably C5-C8 cycloalkyl, and particularly preferably C5-C7 cycloalkyl. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, and cycloheptyl, etc., but not limited thereto.

[0077] As the substrate of the organic electroluminescent device of the present invention, any substrate commonly used in organic electroluminescent devices can be used. Examples are transparent substrates such as glass or transparent plastic substrates; opaque substrates such as silicon substrates. Different substrates have different mechanical strengths, thermal stabilities, transparencies, surface smoothness, and water resistances. Depending on the nature of the substrate, its usage directions are different. In the present invention, a transparent PI film substrate is preferably used. The thickness of the substrate is not particularly limited.

[0078] A first electrode is formed on the substrate, and the first electrode and the second electrode can be opposite to each other. The first electrode can be an anode. The first electrode can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the first electrode is a transmissive electrode, it can 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), etc. When the first electrode is a semi-transmissive electrode or a reflective electrode, it can 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 generally 50 - 500 nm, preferably 70 - 300 nm, and more preferably 100 - 200 nm.

[0079] The organic functional material layer disposed between the first electrode and the second electrode includes a hole transport region, a light-emitting layer, and an electron transport region in sequence from bottom to top.

[0080] In this article, the hole transport region constituting the organic electroluminescent device can include a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0081] As the materials for the hole injection layer, the hole transport layer, and the electron blocking layer, any material can be selected from known related materials for OLED devices for use.

[0082] Examples of the above materials may 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 quinolone derivatives, styryl anthracene 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, styrylamine compounds, triamines, tetraamines, benzidine compounds, propynediamine 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)diphenyl sulfides, bis[4-(diarylamino)phenyl]dimethylmethanes, bis[4-(diarylamino)phenyl]-bis(trifluoromethyl)methanes or 2,2-diphenylethylene compounds, etc.

[0083] Furthermore, according to the device matching requirements, the hole transport film layer between the electron blocking layer and the hole injection layer that constitutes the organic electroluminescent device can be a single film layer or a stacked structure of multiple hole transport materials. In this article, for the above various hole carrier conduction film layers with different functions, their film thicknesses are not particularly limited.

[0084] The hole injection layer contains a host organic material that can conduct holes, and also contains a P-type doping material with a deep HOMO energy level (the corresponding LUMO energy level will also be very deep). Based on empirical summaries, in order to achieve smooth injection of holes from the anode to the organic film layer, the HOMO energy level of the host organic material that conducts holes used in the anode interface buffer layer must have certain characteristics with the P-doping material, so as to be expected to achieve the occurrence of the charge transfer state between the host material and the doping material, achieve Ohmic contact between the buffer layer and the anode, and achieve efficient injection from the electrode to hole injection conduction.

[0085] In view of the above empirical summaries, for hole host materials with different HOMO energy levels, different P-doping materials need to be selected to match them in order to achieve Ohmic contact at the interface and improve the hole injection effect.

[0086] Thus, in one embodiment of the present invention, in order to better inject holes, the hole injection layer further contains a P-type doping 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(cyanomethanylidene))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0087] In the hole injection layer of the present invention, the ratio of the hole transport material to the P-type doping material used is 99:1 - 95:5, preferably 99:1 - 97:3, by mass.

[0088] 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.

[0089] 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.

[0090] 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.

[0091] 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.

[0092] The light-emitting layer can contain a host material and a doping material. The host material can use a common green host material in the art, and the doping material uses the boron-containing organic compound represented by the general formula (1) of the present invention.

[0093] The light-emitting layer can contain a single host material or a double host material;

[0094] The double host material contains a first host material and a second host material. At least one of the first host material and the second host material is preferably a TADF material;

[0095] TADF materials refer to materials with thermally activated delayed fluorescence properties, characterized by having a small energy difference between the first excited singlet state and the first excited triplet state. Therefore, singlet excitons and triplet excitons generated can be utilized simultaneously in the device, enabling the exciton utilization rate of the electroluminescence in the device to approach 100% as much as possible. Compared with traditional fluorescent materials, TADF materials have a higher exciton utilization rate.

[0096] The light-emitting layer may include a host material, an exciton sensitizing material, and a doping material;

[0097] The exciton sensitizing material refers to a material that can enable the luminescent material in the light-emitting layer to fully utilize electroluminescent excitons, so that the light-emitting layer finally generates the emission spectrum of the sensitized material. The exciton sensitizer may undertake functions such as exciton capture, exciton conversion, and exciton transfer in the electroluminescent device. The boron-containing organic compound shown in the general formula (1) of the present invention and the exciton sensitizing material are used in combination, which has an obvious improvement effect on problems such as device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0098] In the light-emitting layer of the present invention, the ratio of the host material to the doping material used is 99:1 - 70:30, preferably 99:1 - 85:15 and more preferably 97:3 - 87:13, based on mass.

[0099] The thickness of the light-emitting layer can be adjusted to optimize the light-emitting efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, further preferably 10 - 50 nm, and more preferably 15 - 40 nm, but the thickness is not limited to this range.

[0100] In the present invention, the electron transport region may sequentially include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer provided on the light-emitting layer, but is not limited thereto.

[0101] 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 prolonging the life of the device and improving the performance of the device. The hole blocking layer of the present invention can be provided on the light-emitting layer. As the hole blocking layer material of the organic electroluminescent device of the present invention, compounds known in the prior art with hole blocking effects can be used, such as phenanthroline derivatives such as bathocuproine (referred to as BCP), metal complexes of hydroxyquinoline derivatives such as aluminum(III) bis(2-methyl-8-quinolinolato)-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.

[0102] The electron transport layer may be disposed above the light-emitting layer or (if present) the hole blocking layer. The electron transport layer material is a material that can easily receive electrons from the cathode and transfer the received electrons to the light-emitting layer. A material with a high electron mobility is preferably used. 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. 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-(naphthalen-2-yl)-1,3,5-triazine (CAS No.: 1459162-51-6) and other triazine derivatives, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-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 can be 10-80 nm, preferably 20-60 nm, and more preferably 25-45 nm, but the thickness is not limited to this range.

[0103] The electron injection layer may be disposed above the electron transport layer. The electron injection layer material is usually preferably a material with a low work function, so that electrons can be easily injected into the organic functional material layer. As the electron injection layer material of the organic electroluminescent device of the present invention, electron injection layer materials known in the prior art for organic electroluminescent devices can be used. For example, lithium; lithium salts such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate, or lithium azide; or cesium salts, cesium fluoride, cesium carbonate, or cesium azide. The thickness of the electron injection layer of the present invention can be 0.1-5 nm, preferably 0.5-3 nm, and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[0104] 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 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, but is not limited thereto. The thickness of the cathode depends on the material used.

[0105] The organic electroluminescent device of the present invention may further include a packaging structure. The packaging structure may be a protective structure for preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The packaging structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.

[0106] A method for preparing the organic electroluminescent device of the present invention includes successively 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 on a substrate, and optionally a covering layer. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI may be used, but are not limited thereto. In the present invention, a vacuum evaporation method is preferably used to form each of the layers. Those skilled in the art can conventionally select each process condition in the vacuum evaporation method according to actual needs.

[0107] The raw materials involved in the synthesis examples of the present invention can all be purchased from the market or prepared by conventional preparation methods in the art;

[0108] Synthesis of Compound 2 in Example 1:

[0109]

[0110] Under nitrogen protection, 20 mmol of raw material A-1, 10 mmol of raw material B-1, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6, and 100 mL of dichlorobenzene were added to a three-necked flask, and the mixture was refluxed for 18 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-1. LC-MS: Measured value: 868.62 ([M+H] + )), theoretical value: 867.34.

[0111] In a three-necked flask, 2.20 mmol of boron tribromide and 1.10 mmol of intermediate a-1 were dissolved in 30 mL of 1,2,4-trichlorobenzene under nitrogen protection. After stirring at 180 °C for 20 hours, the reaction mixture was diluted with dichloromethane (50 mL), and 100 mL of sodium phosphate buffer solution with pH = 6 was added at 0 °C. The aqueous layer was separated and extracted with dichloromethane (100 mL, three times). The crude product was purified by silica gel column chromatography to obtain the target compound 2. FWHM (measured by a Horiba Fluorolog-3 series fluorescence spectrometer in the thin film state): 29 nm.

[0112] Synthesis of Compound 85 in Example 2:

[0113]

[0114] The preparation method of intermediate a-2 is the same as that of intermediate a-1, except that raw material A-2 is used to replace raw material A-1 to obtain intermediate a-2. LC-MS: Measured value: 980.34([M+H] + ), theoretical value: 979.47.

[0115] The preparation method of compound 85 is the same as that of compound 2, except that intermediate a-2 is used to replace intermediate a-1 to obtain compound 85. 1 H NMR(400MHz, Chloroform-d)δ8.68 - 8.52(m, 4H), 7.85 - 7.73(m, 2H), 7.65 - 7.40(m, 10H), 7.15 - 6.95(m, 8H), 6.74(s, 2H), 1.52 - 1.40(s, 18H), 1.35 - 1.29(s, 18H). FWHM (measured by Horiba's Fluorolog-3 series fluorescence spectrometer in the thin film state): 28nm.

[0116] Synthesis of compound 102 in Example 3:

[0117]

[0118] Under nitrogen protection, 10 mmol of raw material C-3, 10 mmol of raw material D-3, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6 and 70 mL of dichlorobenzene were added to a three-necked flask and refluxed for 18 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain raw material A-3. LC-MS: Measured value: 358.41([M+H] + ), theoretical value: 357.16.

[0119] The preparation method of intermediate a-3 is the same as that of intermediate a-1, except that raw material A-3 is used to replace raw material A-1 to obtain intermediate a-3. LC-MS: Measured value: 1020.35([M+H] + ), theoretical value: 1019.41.

[0120] The preparation method of compound 102 is the same as that of compound 2, except that intermediate a-3 is used to replace intermediate a-1 to obtain compound 102. 11H NMR (400 MHz, Chloroform-d) δ 8.67 - 8.50 (m, 4H), 8.25 - 8.20 (m, 2H), 7.86 - 7.70 (m, 2H), 7.62 - 7.18 (m, 22H), 7.16 - 7.01 (m, 4H), 6.74 (s, 2H), 1.46 - 1.41 (s, 18H). FWHM (measured by Horiba's Fluorolog-3 series fluorescence spectrometer in the thin film state): 25 nm.

[0121] Synthesis of Compound 108 in Example 4:

[0122]

[0123] The preparation method of Intermediate a-4 is the same as that of Intermediate a-1, except that raw material A-4 is used to replace raw material A-1, and raw material B-4 is used to replace raw material B-1, to obtain Intermediate a-4. LC-MS: Measured value: 867.22 ([M + H] + ), Theoretical value: 866.35.

[0124] The preparation method of Compound 108 is the same as that of Compound 2, except that Intermediate a-4 is used to replace Intermediate a-1, to obtain Compound 108. 1 1H NMR (400 MHz, Chloroform-d) δ 8.10 (s, 1H), 7.81 - 7.60 (m, 4H), 7.55 - 7.26 (m, 12H), 7.21 (m, 2H), 7.14 - 6.97 (m, 8H), 6.74 (s, 2H), 1.35 - 1.26 (s, 18H). FWHM (measured by Horiba's Fluorolog-3 series fluorescence spectrometer in the thin film state): 26 nm.

[0125] Synthesis of Compound 169 in Example 5:

[0126]

[0127] The preparation method of Intermediate a-5 is the same as that of Intermediate a-1, except that raw material A-5 is used to replace raw material A-1, and raw material B-4 is used to replace raw material B-1, to obtain Intermediate a-5. LC-MS: Measured value: 835.61 ([M + H] + ),Theoretical value: 834.39.

[0128] The preparation method of Compound 169 is the same as that of Compound 2, except that Intermediate a-5 is used to replace Intermediate a-1, to obtain Compound 169. 11H NMR (400 MHz, Chloroform-d) δ 8.13 (s, 1H), 7.50 - 7.24 (m, 16H), 7.21 - 6.99 (m, 10H), 6.74 (s, 2H), 1.39 - 1.30 (s, 18H). FWHM (measured by Horiba's Fluorolog-3 series fluorescence spectrometer in the thin film state): 27 nm.

[0129] Synthesis of Compound 195 in Example 6:

[0130]

[0131] The preparation method of raw material A-6 is the same as that of raw material A-3, except that raw material C-6 is used to replace raw material C-3 and raw material D-6 is used to replace raw material D-3 to obtain raw material A-6. LC-MS: Measured value: 286.29 ([M+H] + ) and the theoretical value: 285.12.

[0132] The preparation method of intermediate a-6 is the same as that of intermediate a-1, except that raw material A-6 is used to replace raw material A-1 to obtain intermediate a-6. LC-MS: Measured value: 876.12 ([M+H] + ) and the theoretical value: 875.33.

[0133] The preparation method of Compound 195 is the same as that of Compound 2, except that intermediate a-6 is used to replace intermediate a-1 to obtain Compound 195. 1 1H NMR (400 MHz, Chloroform-d) δ 8.68 - 8.40 (m, 4H), 7.71 - 7.09 (m, 32H), 6.74 (s, 2H). FWHM (measured by Horiba's Fluorolog-3 series fluorescence spectrometer in the thin film state): 26 nm.

[0134] Synthesis of Compound 230 in Example 7:

[0135]

[0136] The preparation method of intermediate a-7 is the same as that of intermediate a-1, except that raw material A-7 is used to replace raw material A-1 to obtain intermediate a-7. LC-MS: Measured value: 874.24 ([M+H] + ) and the theoretical value: 873.36.

[0137] The preparation method of Compound 230 is the same as that of Compound 2, except that intermediate a-7 is used to replace intermediate a-1 to obtain Compound 230. 11H NMR (400 MHz, Chloroform-d) δ 8.82 - 8.51 (m, 4H), 8.15 - 7.93 (m, 2H), 7.78 - 7.42 (m, 16H), 7.37 - 6.92 (m, 16H), 6.74 (s, 2H). FWHM (measured by Horiba's Fluorolog-3 series fluorescence spectrometer in the thin film state): 28 nm.

[0138] Synthesis of Compound 267 in Example 8:

[0139]

[0140] Under nitrogen protection, 10 mmol of raw material A-8, 10 mmol of raw material B-1, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6 and 70 mL of dichlorobenzene were added to a three-necked flask, and the mixture was refluxed for 18 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-8. LC-MS: Measured value: 651.40 ([M+H] + ), Theoretical value: 650.17.

[0141] Under nitrogen protection, 10 mmol of raw material A-4, 10 mmol of intermediate b-8, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6 and 70 mL of dichlorobenzene were added to a three-necked flask, and the mixture was refluxed for 18 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-8. LC-MS: Measured value: 852.26 ([M+H] + ), Theoretical value: 851.37.

[0142] The preparation method of Compound 267 is the same as that of Compound 2, except that intermediate a-8 is used to replace intermediate a-1 to obtain Compound 267. 1 1H NMR (400 MHz, Chloroform-d) δ 8.60 - 8.51 (m, 4H), 7.88 - 7.63 (m, 2H), 7.60 - 6.95 (m, 20H), 6.74 (s, 2H), 1.37 - 1.30 (d, 18H). FWHM (measured by Horiba's Fluorolog-3 series fluorescence spectrometer in the thin film state): 29 nm.

[0143] The structural characterizations of the compounds obtained in each example are shown in Table 1

[0144] Table 1

[0145]

[0146]

[0147] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 1-8 and Device Comparative Examples 1-4. The manufacturing processes of Device Examples 2-8 and Device Comparative Examples 1-4 are exactly the same as that of Device Example 1, and the same substrate materials and electrode materials are used. The film thicknesses of the electrode materials are also kept consistent. The difference is that the light-emitting layer materials in the devices are replaced. The layer structures and test results of each device example are shown in Table 2 and Table 3 respectively.

[0148] Device Example 1

[0149] As Figure 1 shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed with a cleaning agent (Semiclean M-L20), pure water, and then dried, and then ultraviolet-ozone washing is carried out to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated 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 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as host materials, and Compound 2 is used as a doping material. The mass ratio of GH-1, GH-2, and Compound 2 is 69:30:1, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously evaporated by vacuum evaporation, with a film thickness of 5 nm. This layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously evaporated by vacuum evaporation, and the mass ratio of ET-1 and Liq is 1:1, with a film thickness of 30 nm. This layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated through a vacuum evaporation device. This layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80 nm is fabricated through a vacuum evaporation device. The mass ratio of Mg and Ag is 1:9. This layer is used as the cathode layer 10.

[0150] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 9-16 and Device Comparative Examples 5-8. The manufacturing processes of Device Examples 10-16 and Device Comparative Examples 5-8 of the present invention are exactly the same as those of Device Example 9, and the same substrate materials and electrode materials are used. The film thicknesses of the electrode materials are also kept consistent. The difference is that the light-emitting layer materials in the devices are replaced. The layer structures and test results of each device example are shown in Table 2 and Table 3 respectively.

[0151] Device Example 9

[0152] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed successively with a cleaning agent (Semiclean M-L20), pure water, and 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, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated 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 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-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 doping material, and Compound 2 is used as the second doping material. The mass ratio of GH-1, GH-2, GD-1, and Compound 2 is 66:30:3:1, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously evaporated by vacuum evaporation, with a film thickness of 5 nm. This layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously evaporated by vacuum evaporation, and the mass ratio of ET-1 and Liq is 1:1, with a film thickness of 30 nm. This layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated by a vacuum evaporation device. This layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80 nm is fabricated by a vacuum evaporation device. The mass ratio of Mg and Ag is 1:9. This layer is used as the cathode layer 10.

[0153] The molecular structural formulas of the related materials are as follows:

[0154]

[0155] After the OLED light-emitting device is completed as described above, the anode and cathode are connected by a known drive circuit, and the voltage, current efficiency, and lifetime of the device are measured. The device examples and comparative examples prepared by the same method are shown in Table 2; the test results of the voltage, current efficiency, and lifetime of the obtained devices are shown in Table 3.

[0156] Table 2

[0157]

[0158]

[0159] Table 3

[0160]

[0161] Note: The voltage, current efficiency, and emission peak were measured using an IVL (current-voltage-luminance) test system (Suzhou Fosda Scientific Instruments Co., Ltd.); the lifetime test system was the EAS-62C type OLED device lifetime tester of System Technology Research Co., Ltd. in Japan; LT95 refers to the time taken for the device luminance to decay to 95%; all data were measured at 10 mA / cm 2 below.

[0162] From the device data results in Table 3, it can be seen that compared with Device Comparative Examples 1-4, the device lifetime of the compound of the present invention in the single-doped system device is higher than that of the comparative examples; in the single-doped system device, the device efficiency also shows good results. This is because such a boron-nitrogen fused-ring mother nucleus can adjust the light color, enhance the resonance intensity, and improve the device efficiency; compared with Device Comparative Examples 5-8, in the double-doped system device using an exciton sensitizing material as the first dopant, both the current efficiency and the device lifetime of the device are significantly improved compared to the OLED devices of known materials, and in the double-doped device, the device efficiency is also significantly improved compared to that in the single-doped case.

[0163] In summary, the above are only the 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 shall be included within the protection scope of the present invention.

Claims

1. A boron-containing organic compound, characterized in that, The structure of the organic compound is any one of general formula (IV-1) to general formula (IV-2), general formula (IV-4) to general formula (IV-5): In general formula (IV-1) to general formula (IV-2), general formula (IV-4) to general formula (IV-5), each occurrence of Z1, which may be the same or different, represents C-R3; Each occurrence of Z2, which may be the same or different, represents C-R4; X1 and X2 each independently represent O, S or N(R5); Each occurrence of R3 and R4, which may be the same or different, represents a hydrogen atom, a halogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group; Each occurrence of R5, which may be the same or different, represents one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted biphenyl group; Each occurrence of Z3, which may be the same or different, represents C-R; Each occurrence of R, which may be the same or different, represents a hydrogen atom, a halogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a phenyl-substituted amino group, a tert-butylphenyl-substituted amino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group; The substituents for the substituting groups are each independently selected from one or more of a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, and a cycloalkyl group having 3 to 10 carbon atoms; The boron-containing organic compound does not represent the following compounds:

2. A boron-containing organic compound, characterized in that, The structure of the organic compound is any one of general formula (V-1) and general formula (V-2): In general formula (V-1) and general formula (V-2), each occurrence of Z1, which may be the same or different, represents C-R3; Each occurrence of Z2, which may be the same or different, represents C-R4; X1 and X2 each independently represent O, S or N(R5); Each occurrence of R1, R3, and R4 is the same as or different from each other and represents a hydrogen atom, a halogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group; Each occurrence of R5, which may be the same or different, represents one of a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted biphenyl group; Z4 and Z5 represent N; Each occurrence of Z6 independently represents N or C-H; R a 、R b 、R c 、R d 、R e 、R f Each occurrence, which may be the same or different, represents a hydrogen atom, a halogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted biphenyl group; The substituents for the substituting groups are each independently selected from one or more of a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, and a cycloalkyl group having 3 to 10 carbon atoms; The boron-containing organic compound does not represent the following compounds:

3. The boron-containing organic compound according to claim 1, characterized in that, R3, R4, and R each represent one of a hydrogen atom, a halogen atom, an adamantyl group, a methyl group, a trifluoromethyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a biphenyl group, a naphthyl 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, a phenyl-substituted amino group, and a tert-butylbenzene-substituted amino group; Each R5 represents one of a phenyl group, a biphenyl group, a naphthyl 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, and a tert-butyl-substituted biphenyl group.

4. The boron-containing organic compound according to claim 2, characterized in that, The R1, R3, R4, R a , R b , R c , R d , R e , R f respectively represent one of a hydrogen atom, a halogen atom, an adamantyl group, a methyl group, a trifluoromethyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a biphenyl group, a naphthyl 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, a phenyl-substituted amino group, and a tert-butylbenzene-substituted amino group; Each R5 represents one of a phenyl group, a biphenyl group, a naphthyl 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, and a tert-butyl-substituted biphenyl group.

5. The boron-containing organic compound according to claim 2, wherein The specific structural formula of the organic compound is any one of the following structures:

6. 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 includes a light-emitting layer, characterized in that, The light-emitting layer contains the boron-containing organic compound according to any one of claims 1-5.

7. The organic electroluminescent device according to claim 6, wherein, The light-emitting layer includes a host material and a dopant material, and the dopant material contains the boron-containing organic compound according to any one of claims 1-5.

8. The organic electroluminescent device according to claim 6, wherein the light-emitting layer comprises a first host material, a second host material, and a doping material, characterized in that 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 according to any one of claims 1-5.

9. The organic light-emitting device according to claim 6, wherein the light-emitting layer comprises a host material, an exciton sensitizing material, and a doping material, characterized in that, The exciton sensitizing material is a metal element-containing complex, and the doping material is a boron-containing organic compound as described in any one of claims 1-5.

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