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 can be used as a green light doping material for the light-emitting layer of an organic electroluminescent device, thereby improving the light-emitting 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 and an organic electroluminescent device prepared therefrom. Background Art

[0002] Limited by early technologies, traditional fluorescent doping materials can only utilize 25% of 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 large gap compared with the efficiency of phosphorescent devices. Due to the strong spin-orbit coupling of heavy atom centers in phosphorescent materials, intersystem crossing is enhanced, and both singlet excitons and triplet excitons formed by electrical excitation can be effectively utilized 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 efficiency roll-off of the device, 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, luminescent materials also require 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, to which the human eye is more sensitive, 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 triplet exciton sensitizing materials with fluorescent doping materials. Using triplet exciton sensitizing materials as an exciton sensitization medium, triplet excitons are fully utilized, and energy is transferred to the fluorescent doping materials 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 play 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 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 the lowest singlet and lowest triplet energy level difference less than or equal to 0.2 eV as the host and a boron-containing 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-containing material as the dopant; both can achieve efficiency comparable to phosphorescence and a relatively narrow FWHM. Therefore, developing a sensitization technology based on narrow FWHM boron-based luminescent materials has unique advantages and strong potential for meeting the BT.2020 display indicators. 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 can be used as a green light doping material for the luminescent layer of an organic electroluminescent 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 the general formula (1):

[0008]

[0009] In the general formula (1), each occurrence of Z is the same or different and represents C-R1;

[0010] R1 independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl 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;

[0011] Any two adjacent R1s can be connected to form a ring;

[0012] M1 represents a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0013] R represents a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C 10An alkyl group, a substituted or unsubstituted C3-C 10 A cycloalkyl group, a substituted or unsubstituted C1-C 10 An alkoxy group, a substituted or unsubstituted C6-C 10 An aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 An aryl group, a substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0014] X1 is independently represented as N(R2), O or S;

[0015] R2 is represented as a substituted or unsubstituted C1-C 10 An alkyl group, a substituted or unsubstituted C3-C 10 A cycloalkyl group, a substituted or unsubstituted C6-C 30 An aryl group, a substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0016] Ar1 is represented as a substituted or unsubstituted C1-C 10 An alkyl group, a substituted or unsubstituted C3-C 10 A cycloalkyl group, a substituted or unsubstituted C6-C 30 An aryl group, a substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0017] Ar1 can also form a ring with M1;

[0018] The substituents for the substituents are each independently selected from a deuterium atom, a tritium atom, a halogen atom, a cyano group, a C1-C 10 An alkyl group, a C3-C 10 A cycloalkyl group, a C6-C 30 An aryl group, a C6-C aryl group substituted with a tert-butyl group 30 An aryl group, an arylamino group, a C2-C 30 One or more of the heteroaryl groups.

[0019] In a preferred embodiment, the structure of the boron-containing organic compound is represented by any one of general formulas (2) to (6):

[0020]

[0021] In general formulas (2) to (6), the meanings of Z and X1 are the same as those defined above;

[0022] X2 and X3 are each represented as one of O or S.

[0023] In a preferred embodiment, the structure of the organic compound is represented by any one of general formulas (7) to (27):

[0024]

[0025]

[0026] In General Formulas (7) to (27), the meaning of Z is the same as the definition in the above text;

[0027] Ar2 represents a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0028] The substituents for the substituting groups are each independently selected from a deuterium atom, a tritium 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, or one or more of them.

[0029] In a preferred embodiment, the structure of the organic compound is shown as any one of General Formulas (28) to (31):

[0030]

[0031] In General Formulas (28) to (31), each occurrence of Z, which may be the same or different, represents C-R1;

[0032] R1 each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C 10 alkyl 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;

[0033] Any two adjacent R1s may be connected to form a ring;

[0034] X1 represents N(R2), O or S;

[0035] X2 represents one of O or S;

[0036] R2 represents a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10A cycloalkyl group, a substituted or unsubstituted C6-C 30 An aryl group, a substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0037] Ar1 represents a substituted or unsubstituted C6-C 30 Aryl group, a substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0038] R a , R b , R c , R d , R e Each independently 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 C1-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 One of the heteroaryl groups;

[0039] The substituents for the substituents are each independently selected from a deuterium atom, a tritium 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 One or more of the heteroaryl groups.

[0040] In a preferred embodiment, the R1, R3, R4, R, R a , R b , R c , R d , R eEach is independently represented by one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a cyano group, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a 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 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.

[0041] R2, Ar1, and Ar2 are each represented by one of 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 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 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;

[0042] The substituents for the substituting groups are each independently selected from one or more of a deuterium atom, a chlorine atom, a fluorine atom, an adamantyl group, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-pentyl group, a tert-butyl group, a butyl group, a methoxy group, a phenyl group, a biphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a quinolinyl group, an isoquinolinyl group, a furyl group, a thienyl group, an indolyl group, a pyrrolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a 9,9-dimethylfluorenyl group, a spirofluorene group, a carbazolyl group, an N-phenylcarbazolyl group, a carbazolinyl group, an azaphenanthryl group, a diphenylamino group, and a di-tert-butylphenylamino group.

[0043] In a preferred embodiment, R2, Ar1, and Ar2 are represented by the following structures:

[0044]

[0045] Preferably, R1, R3, R4, R, R a , R b , R c , R d , R e are represented by the following structures: a hydrogen atom, a methyl group,

[0046]

[0047] In a preferred embodiment, the specific structure of the organic compound is any one of the following structures:

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058] The present invention also provides an organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer therebetween. The organic light-emitting functional layer includes a light-emitting layer, and the light-emitting layer contains the boron-containing organic compound described above.

[0059] In a preferred embodiment, the light-emitting layer contains a host material and a dopant material, and the dopant material contains the boron-containing organic compound described above.

[0060] In a preferred embodiment, the light-emitting layer of the organic electroluminescent device contains a first host material, a second host material and a dopant material. At least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-containing organic compound described above.

[0061] In a preferred embodiment, the light-emitting layer of the organic electroluminescent device contains a host material, an exciton sensitizing material and a dopant material. The exciton sensitizing material is a metal element-containing complex, and the dopant material is the boron-containing organic compound described above.

[0062] The beneficial technical effects of the present invention are as follows:

[0063] (1) The compound of the present invention can be used as a dopant material for the light-emitting layer material when applied to an OLED device. Under the action of an electric field, it can emit green fluorescence and can be applied to the fields of OLED lighting or OLED display;

[0064] (2) As a dopant material, the compound of the present invention introduces a TADF sensitizer as the second host, which can effectively improve the device efficiency;

[0065] (3) The spectral FWHM of the compound of the present invention is relatively narrow, which can effectively improve the device color gamut and the light-emitting efficiency of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0066] Figure 1 It is a schematic structural diagram of the materials listed in the present invention applied to an OLED device;

[0067] 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.

[0068] Figure 2 It is the emission spectrum diagram of Compound 92 in toluene solution (5×10 -5 M);

[0069] Figure 3 It is the 1 H NMR spectrum diagram of Compound 92 (400 MHz, deuterated chloroform). DETAILED DESCRIPTION OF THE INVENTION

[0070] Next, in combination with the accompanying drawings in the embodiments of the present invention, the technical solutions in the embodiments of the present invention will be clearly and completely described. Without conflict, the embodiments in the present invention and the features in the embodiments can be combined with each other. The present invention will be further described below in combination with the accompanying drawings and specific embodiments, but it is not a limitation of the present invention.

[0071] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, terms indicating directions such as "upper", "lower", "top", and "bottom" only represent the directions in a specific state, and do not mean that the related structures can only exist in the described directions; on the contrary, if the structure can change its position, for example, be inverted, the direction 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.

[0072] In the present invention, the phrase "can be connected into a ring" means that two groups can be unconnected or can be connected to each other to form a ring, preferably by connecting into a ring through a C-C single bond, an O atom, an S atom, CQ1Q2, or NQ3, where Q1, Q2, and Q3 represent substituted or unsubstituted C1-C 10 alkyl, substituted or unsubstituted C6-C 30 aryl, or substituted or unsubstituted C2-C 30 heteroaryl.

[0073] In the present invention, the arylamino group described in the present invention refers to where Q4 and Q5 represent substituted or unsubstituted aromatic groups, and Q4 and Q5 are preferably represented as substituted or unsubstituted C6-C 30 aryl or substituted or unsubstituted C2-C 30 heteroaryl.

[0074] The arylamino group is preferably:

[0075] In the present invention, the substituted or unsubstituted C6-C 30 aryl refers to substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dimethylfluorenyl, substituted or unsubstituted diphenylfluorenyl, substituted or unsubstituted spirofluorenyl, 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, a combination thereof, or a fused ring of the foregoing group combinations, but not limited thereto.

[0076] In the present invention, the substituted or unsubstituted C2-C 30 Heteroaryl refers to substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted triazolyl, substituted or unsubstituted oxazolyl, substituted or unsubstituted thiazolyl, substituted or unsubstituted oxadiazolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted triazinyl, substituted or unsubstituted 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.

[0077] 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.

[0078] 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.

[0079] The halogen atom in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0080] The C1-C 10 Alkoxy refers to methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, isopropoxy, etc., but not limited thereto.

[0081] 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.

[0082] A first electrode is formed on the substrate, and the first electrode and the second electrode can face 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 usually 50 - 500 nm, preferably 70 - 300 nm, and more preferably 100 - 200 nm.

[0083] The organic functional material layer disposed between the first electrode and the second electrode sequentially includes a hole transport region, a light-emitting layer, and an electron transport region from bottom to top.

[0084] In this article, the hole transport regions constituting the organic electroluminescent device can include a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0085] 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.

[0086] 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 quinone 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 vinylene 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.

[0087] 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-mentioned hole carrier conduction film layers with different functions, their film thicknesses are not particularly limited.

[0088] 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 expect 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.

[0089] 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.

[0090] Therefore, 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-trimethylenetri(cyanomethylidene))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0091] 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.

[0092] 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.

[0093] 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.

[0094] 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.

[0095] 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.

[0096] The light-emitting layer may include a host material and a doping material. The host material may 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.

[0097] The light-emitting layer may include a single host material or a dual host material;

[0098] The dual host material includes 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;

[0099] TADF materials refer to materials with thermally activated delayed fluorescence properties, characterized by a small energy difference between the first excited singlet state and the first excited triplet state. Therefore, singlet excitons and triplet excitons generated simultaneously can be utilized in the device, enabling the utilization rate of excitons generated electrochemically inside the device to approach 100% as much as possible. Compared with traditional fluorescent materials, TADF materials have a higher exciton utilization rate.

[0100] The light-emitting layer may include a host material, an exciton sensitizing material, and a doping material;

[0101] An exciton sensitizing material refers to a material that enables the luminescent material in the light-emitting layer to fully utilize electrochemically generated excitons, thereby enabling the light-emitting layer to ultimately generate the emission spectrum of the sensitized material. Exciton sensitizers may perform functions such as exciton capture, exciton conversion, and exciton transfer in electro-luminescent devices. The boron-containing organic compound represented by 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.

[0102] 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.

[0103] 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.

[0104] 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 above the light-emitting layer, but is not limited thereto.

[0105] The hole blocking layer is a layer that blocks holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the lifespan of the device and improving the performance of the device. The hole blocking layer of the present invention may be provided above the light-emitting layer. As the hole blocking layer material of the organic electro-luminescent 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 may be 2 - 200 nm, preferably 5 - 150 nm, but the thickness is not limited to this range.

[0106] 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-bis(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 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.

[0107] The electron injection layer may be disposed above the electron transport layer. The electron injection layer material is generally 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.

[0108] 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.

[0109] The organic electroluminescent device of the present invention may further include an encapsulation structure. The encapsulation structure may be a protective structure that prevents foreign substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass can or a metal can; or a thin film covering the entire surface of the organic layer.

[0110] The method for preparing the organic electroluminescent device of the present invention comprises 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 successively on a substrate, and optionally a covering layer. In this regard, vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing or LITI methods can be used, but are not limited thereto. In the present invention, it is preferred to use a vacuum evaporation method to form the various layers. Those skilled in the art can conventionally select various process conditions in the vacuum evaporation method according to actual needs.

[0111] The raw materials involved in the synthesis examples of the present invention can be purchased from the market or prepared by conventional preparation methods in the art;

[0112] Example 1 Synthesis of Compound 26:

[0113]

[0114]

[0115] Under nitrogen protection, 10 mmol of raw material A-1, 11 mmol of raw material B-1, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine and 40 mL of anhydrous DMF were added to a three-necked flask and refluxed for 12 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: 524.14 ([M+H] + ), theoretical value: 523.16.

[0116] Under nitrogen protection, 10 mmol of raw material D-1, 11 mmol of raw material C-1, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 30 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate b-1. LC-MS: Measured value: 345.11 ([M+H] + ), theoretical value: 344.02.

[0117] Under nitrogen protection, 10 mmol of intermediate b-1, 12 mmol of bis(pinacolato)diboron, 15 mmol of sodium acetate, 0.5 mmol of Pd(dppf)Cl2, and 50 mL of 1,4-dioxane were added to a three-necked flask, and the mixture was refluxed for 15 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-1. LC-MS: Measured value: 393.22 ([M+H] + ), theoretical value: 392.20.

[0118] Under nitrogen protection, 10 mmol of intermediate c-1, 10 mmol of intermediate a-1, 20 ml of toluene, 1 ml of water, 15 mmol of potassium carbonate, and 0.2 mmol of Pd(PPh3)4 were added to a three-necked flask, and the mixture was refluxed for 10 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate d-1. LC-MS: Measured value: 710.31 ([M+H] + ), theoretical value: 709.35.

[0119] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate d-1 and 5 ml of o-xylene were added. A 12 mmol solution of tert-butyllithium in n-hexane was added at 0 °C, the system was heated to 60 °C and reacted for 2 hours, then 15 mmol of boron tribromide was added at 0 °C, the mixture was transferred to room temperature and reacted for another 2 hours, and then 20 mmol of N,N-diisopropylethylamine was added to the system at 0 °C, and the mixture was heated to 200 °C and reacted for 12 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 26, FWHM in toluene solution (1×10 -5 M): 30 nm.

[0120] Synthesis of compound 34 in Example 2:

[0121]

[0122] Under nitrogen protection, 10 mmol of raw material A-2, 12 mmol of bis(pinacolato)diboron, 15 mmol of sodium acetate, 0.5 mmol of Pd(dppf)Cl2, and 50 mL of 1,4-dioxane were added to a three-necked flask, and the mixture was refluxed for 11 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-2. LC-MS: Measured value: 396.30 ([M+H] + ), theoretical value: 395.21.

[0123] Under nitrogen protection, 10 mmol of intermediate a-2, 10 mmol of intermediate a-1, 20 ml of toluene, 1 ml of water, 15 mmol of potassium carbonate and 0.2 mmol of Pd(PPh3)4 were added to a three-necked flask, and the mixture was refluxed for 10 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-2. LC-MS: Measured value: 713.30([M+H] + ), theoretical value: 712.36.

[0124] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-2 and 5 ml of o-dichlorobenzene were added. A solution of 12 mmol of tert-butyllithium in n-hexane was added at 0 °C, the system was heated to 60 °C and reacted for 2 hours. Then, 15 mmol of boron tribromide was added at 0 °C, and the reaction was continued at room temperature for 3 hours. Then, 20 mmol of N,N-diisopropylethylamine was added to the system at 0 °C, and the mixture was heated to 200 °C and reacted for 6 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 34. 1 HNMR(400MHz, chloroform-d) δ8.23(d,1H),7.95(dd,1H),7.81(d,1H),7.78-7.66(m,2H),7.64-7.59(m,2H),7.55-7.45(m,5H),7.40-7.33(m,2H),7.28-7.16(m,5H),7.08(d,1H),1.44(s,9H),1.41(d,18H). FWHM in toluene solution (1×10 -5 M): 29 nm.

[0125] Synthesis of compound 41 in Example 3:

[0126] Preparation of raw material C-3:

[0127]

[0128] In a 500 ml two-necked flask, raw material M-1 (30.80 mmol), copper(I) iodide (1.54 mmol), diethylenetriamine (3.08 mmol), sodium iodide (60.16 mmol) and 300 ml of anhydrous acetonitrile were added, and the mixture was heated under reflux for 18 h. After cooling, it was extracted with ethyl acetate, and the acetonitrile was washed away with saturated brine. The organic phase was dried over anhydrous sodium sulfate, the solvent was evaporated, and the residue was triturated with methanol. The solid was recrystallized from dichloromethane-methanol to obtain raw material C-3.

[0129]

[0130] Under nitrogen protection, 10 mmol of raw material A-3, 11 mmol of raw material D-1, 15 mmol of sodium tert-butoxide, 0.5 mmol of palladium acetate, 1.5 mmol of tri-tert-butylphosphine and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 30 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-3. LC-MS: Measured value: 329.06 ([M+H] + ), theoretical value: 328.05.

[0131] Under nitrogen protection, 10 mmol of intermediate a-3, 12 mmol of biboric acid pinacol ester, 15 mmol of sodium acetate, 0.5 mmol of Pd(dppf)Cl2, and 50 mL of 1,4-dioxane were added to a three-necked flask and refluxed for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-3. LC-MS: Measured value: 377.31 ([M+H] + ), theoretical value: 376.22.

[0132] Under nitrogen protection, 10 mmol of intermediate b-3, 10 mmol of raw material A-1, 20 ml of toluene, 1 ml of water, 15 mmol of potassium carbonate and 0.2 mmol of Pd(PPh3)4 were added to a three-necked flask and refluxed for 8 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-3. LC-MS: Measured value: 495.13 ([M+H] + ), theoretical value: 494.10.

[0133] Under nitrogen protection, 10 mmol of intermediate c-3, 11 mmol of raw material B-3, 15 mmol of sodium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 11 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate d-3. LC-MS: Measured value: 564.33 ([M+H] + ), theoretical value: 563.30.

[0134] Under nitrogen protection, 10 mmol of intermediate d-3, 11 mmol of raw material C-3, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine and 40 mL of anhydrous toluene were added to a three-necked flask and refluxed for 20 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate e-3. LC-MS: Measured value: 752.47 ([M+H] + ), theoretical value: 751.36.

[0135] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate e-3 and 5 ml of o-dichlorobenzene were added. 12 mmol of tert-butyl lithium in n-hexane solution was added at 0°C, the system was heated to 60°C and reacted for 3 hours, then 15 mmol of boron tribromide was added at 0°C, the reaction was continued at room temperature for 3 hours, then 20 mmol of N,N-diisopropylethylamine was added to the system at 0°C, the reaction was heated to 200°C and reacted for 7 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 41. 1 HNMR (400MHz, deuterated chloroform) δ8.05-7.93 (m, 1H), 7.81-7.73 (m, 1H), 7.68-7.61 (m, 2H), 7.55-7.36 (m, 7H), 7.30-7.24 (m, 3H), 7.16-7.09 (m, 2H), 1.35 (d, 27H), 1.31 (s, 9H). Toluene solution (1×10 -5 M) FWHM: 31nm.

[0136] Example 4 Synthesis of Compound 52:

[0137]

[0138] Under nitrogen protection, 10 mmol of intermediate c-1, 10 mmol of raw material A-1, 20 ml of toluene, 1 ml of water, 15 mmol of potassium carbonate and 0.2 mmol of Pd(PPh3)4 were added to a three-necked flask and refluxed for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-4. LC-MS: Measured value: 511.13 ([M+H] + ), theoretical value: 510.08.

[0139] Under nitrogen protection, 10 mmol of raw material A-4, 10 mmol of intermediate a-4, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine and 20 mL of anhydrous toluene were added to a three-necked flask and refluxed for 40 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate b-4. LC-MS: Measured value: 765.33 ([M+H] + ), theoretical value: 764.30.

[0140] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-4 and 5 ml of o-dichlorobenzene were added. 12 mmol of tert-butyl lithium in n-hexane solution was added at 0°C, the system was heated to 60°C and reacted for 6 hours, then 15 mmol of boron tribromide was added at 0°C, the reaction was continued at room temperature for 5 hours, then 20 mmol of N,N-diisopropylethylamine was added to the system at 0°C, the reaction was heated to 200°C and reacted for 12 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 52. 1 HNMR (400MHz, deuterated chloroform) δ8.20-8.13 (m, 2H), 8.02 (m, 2H), 7.96-7.90 (m, 1H), 7.84-7.78 (m, 2H), 7.72-7.69 (m, 4H), 7.65-7.58 (m, 2H), 7.56-7.41 (m, 5H), 7.33 (d, 1H), 7.27-7.11 (m, 6H), 1.45 (s, 9H), 1.37 (s, 9H). Toluene solution (1×10 -5 M) FWHM: 33nm.

[0141] Example 5 Synthesis of Compound 110:

[0142]

[0143] Under nitrogen protection, 10 mmol of intermediate c-1, 10 mmol of raw material A-5, 20 ml of toluene, 1 ml of water, 15 mmol of potassium carbonate and 0.2 mmol of Pd(PPh3)4 were added to a three-necked flask and refluxed for 10 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-5. LC-MS: Measured value: 531.12 ([M+H] + ), theoretical value: 530.05.

[0144] Under nitrogen protection, 10 mmol of intermediate a-5, 10 mmol of raw material B-5, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine and 20 mL of anhydrous toluene were added to a three-necked flask and refluxed for 11 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-5. LC-MS: Measured value: 652.26 ([M+H] + ), theoretical value: 651.27.

[0145] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-5 and 5 ml of o-dichlorobenzene were added. 12 mmol of tert-butyl lithium in n-hexane was added at 0°C, the system was heated to 60°C and reacted for 3 hours, then 15 mmol of boron tribromide was added at 0°C, the reaction was continued at room temperature for 2 hours, then 20 mmol of N,N-diisopropylethylamine was added to the system at 0°C, the reaction was heated to 200°C and reacted for 11 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 110. 1 H NMR (400MHz, deuterated chloroform) δ7.86 (m, 1H), 7.69 (m, 1H), 7.62-7.51 (m, 2H), 7.46-7.28 (m, 10H), 7.19-7.13 (m, 2H), 7.02 (m, 1H), 2.20-2.15 (m, 1H), 2.11-1.90 (m, 3H), 1.66-1.45 (m, 4H), 1.36-1.22 (m, 15H). Toluene solution (1×10 -5 M) FWHM: 34nm.

[0146] Example 6 Synthesis of Compound 181:

[0147]

[0148] Under nitrogen protection, 10 mmol of intermediate a-5, 10 mmol of raw material A-6, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine and 20 mL of anhydrous toluene were added to a three-necked flask and refluxed for 16 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-6. LC-MS: Measured value: 732.36 ([M+H] + ), theoretical value: 731.34.

[0149] Under nitrogen protection, 10 mmol of intermediate a-6, 10 mmol of raw material B-6, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine and 20 mL of anhydrous toluene were added to a three-necked flask and refluxed for 16 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-6. LC-MS: Measured value: 864.38 ([M+H] + ), theoretical value: 863.43.

[0150] In a sealed pressure tube, under nitrogen protection, 10 mmol of intermediate b-6 and 5 ml of o-dichlorobenzene were added. 12 mmol of tert-butyl lithium in n-hexane was added at 0°C, the system was heated to 60°C and reacted for 6 hours, then 15 mmol of boron tribromide was added at 0°C, the system was transferred to room temperature and continued to react for 3 hours, then 20 mmol of N,N-diisopropylethylamine was added to the system at 0°C, heated to 200°C and reacted for 10 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 181. Toluene solution (1×10 -5 M) FWHM: 29nm.

[0151] Example 7 Synthesis of Compound 200:

[0152]

[0153] Preparation of raw material A-7:

[0154] Under nitrogen protection, raw material F-1 (17.8mmol) was dissolved in anhydrous THF (50mL), the reaction system was cooled to 0°C, and a solution of concentrated hydrochloric acid (8.2mL) in water (25mL) was slowly added dropwise. After the addition was completed, a solution of NaNO2 (26.7mmol) in water (10mL) was slowly added dropwise, and the reaction temperature was kept below 5°C. After the addition was completed, the reaction system continued to stir for 15 minutes. A solution of KI (35.5mol) in water (37.2mL) was added dropwise to the reaction system, and the reaction temperature was kept below 5°C. After the addition was completed, the temperature was maintained and stirred for 2h. Subsequently, the reaction was quenched with a saturated sodium sulfite solution, extracted with ethyl acetate and washed with saturated brine in turn, dried over anhydrous Na2SO4, the solvent was spin-dried, and column chromatography was performed to obtain raw material A-7.

[0155]

[0156] Under nitrogen protection, 10 mmol of raw material A-7, 10 mmol of raw material C-1, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine and 20 mL of anhydrous toluene were added to a three-necked flask and refluxed for 15 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate a-7. LC-MS: Measured value: 477.20 ([M+H] + ), theoretical value: 476.12.

[0157] Under nitrogen protection, 10 mmol of intermediate a-7, 12 mmol of biboric acid pinacol ester, 15 mmol of sodium acetate, 0.5 mmol of Pd(dppf)Cl2, and 50 mL of 1,4-dioxane were added to a three-necked flask and refluxed for 19 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-7. LC-MS: Measured value: 525.25 ([M+H] + ), theoretical value: 524.29.

[0158] Under nitrogen protection, 10 mmol of intermediate b-7, 10 mmol of raw material A-1, 20 ml of toluene, 1 ml of water, 15 mmol of potassium carbonate and 0.2 mmol of Pd(PPh3)4 were added to a three-necked flask and refluxed for 12 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-7. LC-MS: Measured value: 643.20 ([M+H] + ), theoretical value: 642.17.

[0159] Under nitrogen protection, 10 mmol of intermediate c-7, 10 mmol of raw material B-3, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine and 20 mL of anhydrous toluene were added to a three-necked flask and refluxed for 20 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate d-7. LC-MS: Measured value: 712.41 ([M+H] + ), theoretical value: 711.37.

[0160] Under nitrogen protection, 10 mmol of intermediate d-7, 10 mmol of raw material C-3, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine and 20 mL of anhydrous toluene were added to a three-necked flask and refluxed for 16 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate e-7. LC-MS: Measured value: 900.51 ([M+H] + ), theoretical value: 899.43.

[0161] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate e-7 and 5 ml of o-dichlorobenzene were added. 12 mmol of tert-butyl lithium in n-hexane was added at 0°C, the system was heated to 60°C and reacted for 2 hours, then 15 mmol of boron tribromide was added at 0°C, the reaction was continued at room temperature for 4 hours, then 20 mmol of N,N-diisopropylethylamine was added to the system at 0°C, heated to 200°C and reacted for 10 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 200. 1 H NMR (400MHz, deuterated chloroform) δ7.91 (m, 1H), 7.80 (d, 1H), 7.74-7.67 (m, 2H), 7.62 (d, 1H), 7.55-7.30 (m, 8H), 7.29-7.22 (m, 4H), 7.17-7.13 (m, 2H), 1.52-1.44 (m, 36H), 1.41 (s, 9H). Toluene solution (1×10 -5 M) FWHM: 30nm.

[0162] Example 8 Synthesis of Compound 237:

[0163]

[0164] Under nitrogen protection, 10 mmol of intermediate b-7, 10 mmol of raw material A-8, 20 ml of toluene, 1 ml of water, 15 mmol of potassium carbonate and 0.2 mmol of Pd(PPh3)4 were added to a three-necked flask and refluxed for 16 hours. After the reaction, 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: 866.36 ([M+H] + ), theoretical value: 865.31.

[0165] Under nitrogen protection, 10 mmol of intermediate a-8, 10 mmol of raw material B-1, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine and 20 mL of anhydrous toluene were added to a three-necked flask and refluxed for 24 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain intermediate b-8. LC-MS: Measured value: 1065.60 ([M+H] + ), theoretical value: 1064.58.

[0166] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-8 and 5 ml of o-dichlorobenzene were added. 12 mmol of tert-butyl lithium in n-hexane was added at 0°C, the system was heated to 60°C and reacted for 2 hours, then 15 mmol of boron tribromide was added at 0°C, the reaction was continued at room temperature for 5 hours, then 20 mmol of N,N-diisopropylethylamine was added to the system at 0°C, the reaction was heated to 200°C and reacted for 5 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 237. 1 HNMR (400MHz, deuterated chloroform) δ8.36 (m, 1H), 8.05 (d, 1H), 7.92 (m, 1H), 7.85-7.72 (m, 2H), 7.61-7.49 (m, 6H), 7.46-7.37 (m, 3H), 7.34-7.20 (m, 5H), 7.13 (m, 2H), 7.09-7.01 (m, 4H), 1.40-1.25 (m, 54H). Toluene solution (1×10 -5 M) FWHM: 27nm.

[0167] FWHM (half width) was measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0168] Example 9 Synthesis of Compound 92:

[0169]

[0170] Under nitrogen protection, 10 mmol of raw material B-1, 10 mmol of intermediate a-5, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine and 20 mL of anhydrous toluene were added to a three-necked flask and refluxed for 20 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-9. LC-MS: Measured value: 730.37 ([M+H] + ), theoretical value: 729.32.

[0171] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-9 and 5 ml of o-dichlorobenzene were added. 12 mmol of tert-butyl lithium in n-hexane was added at 0°C, the system was heated to 60°C and reacted for 3 hours, then 15 mmol of boron tribromide was added at 0°C, the system was transferred to room temperature and continued to react for 3 hours, then 20 mmol of N,N-diisopropylethylamine was added to the system at 0°C, heated to 200°C and reacted for 15 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 92. Compound 92 was dissolved in a toluene solution (1×10 -5M) FWHM: 37 nm. The spectrum of Compound 92 in toluene solution (5×10 -5 M) is shown in the appendix Figure 2 , and the 1 1H NMR spectrum of Compound 92 is shown in the appendix Figure 3 .

[0172] The structural characterizations of the compounds obtained in each example are shown in Table 1

[0173] Table 1

[0174]

[0175] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 1-9 and Device Comparative Examples 1-2. The manufacturing processes of the devices of Device Examples 2-9 and Device Comparative Examples 1-2 are exactly the same as those of Device Example 1, and the same substrate materials and electrode materials are used, and the film thicknesses of the electrode materials are also 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 Tables 2-1 and 3 respectively:

[0176] Device Example 1

[0177] As Figure 1As 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 successively with a cleaning agent (Semiclean M-L20), pure water, and then 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 device is fabricated. GH-1 and GH-2 are used as the host materials, and compound 26 is used as the doping material. The mass ratio of GH-1, GH-2, and compound 26 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, and 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, and 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, and 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, and the mass ratio of Mg and Ag is 1:9, and this layer is used as the cathode layer 10.

[0178] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through device examples 10-18 and device comparative examples 3-4. The manufacturing processes of the devices in device examples 10-18 and device comparative examples 3-4 of the present invention are exactly the same as that of device example 10, and the same substrate materials and electrode materials are used, and 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 Tables 2-2 and 3 respectively:

[0179] Device Example 10

[0180] 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 then 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, using GH-1 and GH-2 as the host materials, GD-1 as the first doping material, and compound 26 as the second doping material. The mass ratio of GH-1, GH-2, GD-1, and compound 26 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 vacuum-evaporated with a film thickness of 5 nm, and this layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously vacuum-evaporated, and the mass ratio of ET-1 and Liq is 1:1, with a film thickness of 30 nm, and 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, and 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, and the mass ratio of Mg and Ag is 1:9, and this layer is used as the cathode layer 10.

[0181] The molecular structural formulas of the related materials are as follows:

[0182]

[0183] After the OLED light-emitting device is completed as described above, the anode and the cathode are connected by a known driving circuit, and the current efficiency, external quantum efficiency, and the lifetime of the device are measured. The device examples and comparative examples prepared by the same method are shown in Tables 2-1 and 2-2; the test results of the current efficiency, external quantum efficiency, and lifetime of the obtained devices are shown in Table 3.

[0184] Table 2-1

[0185]

[0186]

[0187] Table 2-2

[0188]

[0189]

[0190] Table 3

[0191]

[0192] Note: The current efficiency and emission peak are measured using an IVL (current-voltage-luminance) test system (Suzhou FushiDa Scientific Instruments Co., Ltd.); the lifetime test system is the EAS-62C type OLED device lifetime tester of System Technology Research Co., Ltd. of Japan; LT95 refers to the time taken for the device luminance to decay to 95%; all data are measured at 10 mA / cm 2 below.

[0193] It can be seen from the device data results in Table 3 that compared with Device Comparative Examples 1-4, both the current efficiency and device lifetime of the organic light-emitting device of the present invention are significantly improved compared to OLED devices made of known materials; when using an exciton sensitizing material as the first dopant, the device efficiency is significantly improved compared to single doping.

[0194] 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 boron-containing organic compound is as shown in general formula (3): In general formula (3), each occurrence of Z, which may be the same or different, represents C-R1; R1 independently represents one of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a phenyl group substituted with a methyl group, a phenyl group substituted with an ethyl group, a phenyl group substituted with an isopropyl group, a phenyl group substituted with a tert-butyl group, a biphenyl group substituted with a methyl group, a biphenyl group substituted with an ethyl group, a biphenyl group substituted with an isopropyl group, a biphenyl group substituted with a tert-butyl group, a phenyl group substituted with a deuterated methyl group, a phenyl group substituted with a deuterated ethyl group, a phenyl group substituted with a deuterated isopropyl group, a phenyl group substituted with a deuterated tert-butyl group, a biphenyl group substituted with a deuterated methyl group, a biphenyl group substituted with a deuterated ethyl group, a biphenyl group substituted with a deuterated isopropyl group, a biphenyl group substituted with a deuterated tert-butyl group, an amino group substituted with a phenyl group, and an amino group substituted with a tert-butylbenzene; Each occurrence of X1 independently represents N(R2), O or S; R2 represents one of a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a phenyl group substituted with a methyl group, a phenyl group substituted with an ethyl group, a phenyl group substituted with an isopropyl group, a phenyl group substituted with a tert-butyl group, a biphenyl group substituted with a methyl group, a biphenyl group substituted with an ethyl group, a biphenyl group substituted with an isopropyl group, a biphenyl group substituted with a tert-butyl group, a phenyl group substituted with a deuterated methyl group, a phenyl group substituted with a deuterated ethyl group, a phenyl group substituted with a deuterated isopropyl group, a phenyl group substituted with a deuterated tert-butyl group, a biphenyl group substituted with a deuterated methyl group, a biphenyl group substituted with a deuterated ethyl group, a biphenyl group substituted with a deuterated isopropyl group, and a biphenyl group substituted with a deuterated tert-butyl group.

2. The boron-containing organic compound according to claim 1, wherein The structure of the organic compound is as shown in any one of general formula (8), general formula (14) or general formula (20): In general formula (8), general formula (14) and general formula (20), the meaning of Z is the same as the definition in claim 1; Ar2 represents one of a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a phenyl group substituted with a methyl group, a phenyl group substituted with an ethyl group, a phenyl group substituted with an isopropyl group, a phenyl group substituted with a tert-butyl group, a biphenyl group substituted with a methyl group, a biphenyl group substituted with an ethyl group, a biphenyl group substituted with an isopropyl group, a biphenyl group substituted with a tert-butyl group, a phenyl group substituted with a deuterated methyl group, a phenyl group substituted with a deuterated ethyl group, a phenyl group substituted with a deuterated isopropyl group, a phenyl group substituted with a deuterated tert-butyl group, a biphenyl group substituted with a deuterated methyl group, a biphenyl group substituted with a deuterated ethyl group, a biphenyl group substituted with a deuterated isopropyl group, and a biphenyl group substituted with a deuterated tert-butyl group.

3. A boron-containing organic compound, characterized in that, The structure of the organic compound is as shown in general formula (28): In general formula (28), each occurrence of Z, which may be the same or different, represents C-R1; R1 is independently represented by one of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a phenyl group substituted with a methyl group, a phenyl group substituted with an ethyl group, a phenyl group substituted with an isopropyl group, a phenyl group substituted with a tert-butyl group, a biphenyl group substituted with a methyl group, a biphenyl group substituted with an ethyl group, a biphenyl group substituted with an isopropyl group, a biphenyl group substituted with a tert-butyl group, a phenyl group substituted with a deuterated methyl group, a phenyl group substituted with a deuterated ethyl group, a phenyl group substituted with a deuterated isopropyl group, a phenyl group substituted with a deuterated tert-butyl group, a biphenyl group substituted with a deuterated methyl group, a biphenyl group substituted with a deuterated ethyl group, a biphenyl group substituted with a deuterated isopropyl group, a biphenyl group substituted with a deuterated tert-butyl group, an amino group substituted with a phenyl group, and an amino group substituted with a tert-butylbenzene; X1 is represented by N(R2), O or S; R2 is represented by one of a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a phenyl group substituted with a methyl group, a phenyl group substituted with an ethyl group, a phenyl group substituted with an isopropyl group, a phenyl group substituted with a tert-butyl group, a biphenyl group substituted with a methyl group, a biphenyl group substituted with an ethyl group, a biphenyl group substituted with an isopropyl group, a biphenyl group substituted with a tert-butyl group, a phenyl group substituted with a deuterated methyl group, a phenyl group substituted with a deuterated ethyl group, a phenyl group substituted with a deuterated isopropyl group, a phenyl group substituted with a deuterated tert-butyl group, a biphenyl group substituted with a deuterated methyl group, a biphenyl group substituted with a deuterated ethyl group, a biphenyl group substituted with a deuterated isopropyl group, and a biphenyl group substituted with a deuterated tert-butyl group; R b is one of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a phenyl group substituted with a methyl group, a phenyl group substituted with an ethyl group, a phenyl group substituted with an isopropyl group, a phenyl group substituted with a tert-butyl group, a biphenyl group substituted with a methyl group, a biphenyl group substituted with an ethyl group, a biphenyl group substituted with an isopropyl group, a biphenyl group substituted with a tert-butyl group, a phenyl group substituted with a deuterated methyl group, a phenyl group substituted with a deuterated ethyl group, a phenyl group substituted with a deuterated isopropyl group, a phenyl group substituted with a deuterated tert-butyl group, a biphenyl group substituted with a deuterated methyl group, a biphenyl group substituted with a deuterated ethyl group, a biphenyl group substituted with a deuterated isopropyl group, a biphenyl group substituted with a deuterated tert-butyl group, an amino group substituted with a phenyl group, and an amino group substituted with a tert-butylbenzene; R a 、R c 、R d 、R e each independently represents one of a hydrogen atom, a deuterium atom, a methyl group, a deuterated methyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl 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, an amino group substituted with a tert-butylbenzene 4. The boron-containing organic compound according to any one of claims 1 or 3, characterized in that, The R2 is represented as the following structure: any one of; 5. The boron-containing organic compound according to any one of claims 1-2, characterized in that, The R1 is represented by the following structure: a hydrogen atom, a methyl group, any one of them.

6. The boron-containing organic compound according to claim 3, characterized in that, The R1 is represented by the following structure: a hydrogen atom, a methyl group, any one of which.

7. The boron-containing organic compound according to claim 3, wherein The R b is represented by the following structure: a hydrogen atom, a methyl group, any one of; The R a , R c , R d , R e is represented in the following structure: a hydrogen atom, a methyl group, any one of 8. A boron-containing organic compound, characterized in that, The specific structure of the organic compound is any one of the following structures:

9. An organic electroluminescent device includes a cathode and an anode, and an organic light-emitting functional layer therebetween, and the organic light-emitting functional layer includes a light-emitting layer, and is characterized in that, The light-emitting layer contains the boron-containing organic compound according to any one of claims 1-8.

10. The organic electroluminescent device according to claim 9, characterized in that, The light-emitting layer includes a host material and a doping material, and the doping material contains the boron-containing organic compound according to any one of claims 1-8.

11. The organic electroluminescent device according to claim 9, 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 doping material is the boron-containing organic compound according to any one of claims 1-8.

12. The organic electroluminescent device according to claim 9, wherein the light-emitting layer comprises a host material, an exciton sensitizing material, and a doping material, and is characterized in that: The exciton sensitizing material is a metal element-containing complex, and the doping material is the boron-containing organic compound according to any one of claims 1-8.

Images