A boron-containing organic compound with a carbazole-fluorene structure and an organic electroluminescent device prepared therefrom

Abstract

The present invention discloses a boron-containing organic compound having a carbazole-fluorene structure 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). When the compound of the present invention is used as a doping material in the light-emitting layer material of an OLED light-emitting device, it 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 efficiency 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 having a carbazole-fluorene structure and an organic electroluminescent device prepared therefrom. 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 large 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, have 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, the luminescent material also requires a narrower full width at half maximum to improve the color purity of the device luminescence. Fluorescent doping materials can achieve high fluorescence quantum 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 below 30 nm. In the green light region, which is more sensitive to the human eye, the research mainly focuses on phosphorescent doping materials, but it is difficult to narrow their emission peak shape by 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 sensitizing 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 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 singlet-triplet energy gap 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 sensitization technologies based on narrow FWHM boron-based luminescent materials has unique advantages and strong potential in 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 containing a carbazole-fluorene structure and an organic light-emitting device prepared therefrom. By introducing a spiro structure at a specific position of the boron-nitrogen fused ring mother nucleus, the compound of the present invention can be used as a green dopant material for the light-emitting layer of an organic light-emitting 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 containing a carbazole-fluorene structure, wherein 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, which is the same or different, represents C-R;

[0010] Each occurrence of R, which is the same or different, represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a substituted or unsubstituted C 1 ~C 10 alkoxy group, a substituted or unsubstituted C 1 ~C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group;

[0011] Z 1 、Z 2 、Z 3 each independently represents C-Ra , C-R b , C-R c ;

[0012] R a , R b , R c independently represent a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C 1 ~C 10 alkyl, a substituted or unsubstituted C 3 ~C 10 cycloalkyl, a substituted or unsubstituted C 1 ~C 10 alkoxy, a substituted or unsubstituted C 1 ~C 10 aryloxy, a substituted or unsubstituted arylamino, a substituted or unsubstituted C 6 ~C 30 aryl, a substituted or unsubstituted C 2 ~C 30 heteroaryl;

[0013] R 1 , R 2 each independently represent a substituted or unsubstituted C 6 ~C 30 aryl, a substituted or unsubstituted C 2 ~C 30 heteroaryl; R 1 and R 2 can be connected to form a ring;

[0014] M 1 represents a substituted or unsubstituted C 6 ~C 30 aryl, a substituted or unsubstituted C 2 ~C 30 heteroaryl;

[0015] X represents N(R 3 ), C(R 4 )(R 5 ), Si(R 6 )(R 7 ), O, or S;

[0016] R 3 , R 4 , R 5 , R 6 , R 7 each independently represent a substituted or unsubstituted C 1 ~C 10 alkyl, a substituted or unsubstituted C 3 ~C10 a cycloalkyl group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group; R 3 may be connected to M1 to form a ring;

[0017] The substituents for the substituting groups are each independently selected from a deuterium atom, a tritium atom, a halogen atom, a C 1 ~C 10 alkyl group, a C 3 ~C 10 cycloalkyl group, a C 6 ~C 30 aryl group, a C 2 ~C 30 heteroaryl group;

[0018] The heteroatoms in the heteroaryl group are each independently selected from O, S, N, Si.

[0019] In a preferred embodiment, the structure of the organic compound is represented by general formula (2) to general formula (9):

[0020]

[0021] In general formula (2) - general formula (9), R 1 , R 2 , R 3 , Z, Z 1 , Z 2 , Z 3 have the same meanings as defined above;

[0022] R 8 -R 13 each independently represents a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group;

[0023] Y 1 , Y 2 , Y 3 , Y 5 each independently represents O, S, N(R 14 ) ;

[0024] Y 4 represents O or S;

[0025] R 14 represents a substituted or unsubstituted C 6 ~C 30An aryl, a substituted or unsubstituted C 2 ~C 30 heteroaryl; R 14 may be linked to the adjacent benzene ring to form a ring;

[0026] The substituents for the substituting groups are each independently selected from a deuterium atom, a tritium atom, a halogen atom, a C 1 ~C 10 alkyl, a C 3 ~C 10 cycloalkyl, a C 6 ~C 30 aryl, a C 2 ~C 30 heteroaryl;

[0027] The heteroatoms in the heteroaryl are each independently selected from O, S, N, Si.

[0028] In a preferred embodiment, the structure of the organic compound is represented by any one of general formula (10) to general formula (29):

[0029]

[0030]

[0031] In general formula (10) to general formula (29), the meanings of Z, Z 1 , Z 2 , Z 3 are the same as defined above.

[0032] In a preferred embodiment, the structure of the organic compound is represented by any one of general formula (30) to general formula (40):

[0033]

[0034]

[0035] In general formula (30) to general formula (40), the definitions of the said Z, R b are the same as defined above.

[0036] In a preferred embodiment, the structure of the organic compound is represented by any one of general formula (41) to general formula (46):

[0037]

[0038] In general formula (41) to general formula (46), the meanings of Z, Z 1 , Z 2 , Z 3 , R 3 are the same as defined above;

[0039] The Ar 1 is represented as a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group;

[0040] The substituents for the substituting groups are each independently selected from a deuterium atom, a tritium atom, a halogen atom, a C 1 -C 10 alkyl group, a C 3 -C 10 cycloalkyl group, a C 6 -C 30 aryl group, a C 2 -C 30 heteroaryl group, or a combination thereof;

[0041] The heteroatoms in the heteroaryl group are each independently selected from O, S, N, and Si.

[0042] In a preferred embodiment, the R, R a , R b , R c , R 3 , R 14 , Ar 1 are represented by the following structures:

[0043]

[0044]

[0045] The M 1 is represented by any one of the following ring structures:

[0046]

[0047] The definition of Z is the same as that defined above.

[0048] In a preferred embodiment, the R, R a , R b , R cEach is independently represented by 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 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;

[0049] Said R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 、R 8 、R 9 、R 10 、R 11 、R 12 、R 13 、R 14 、Ar 1Each is independently represented by one of adamantyl, methyl, deuterated methyl, tritiated methyl, trifluoromethyl, ethyl, deuterated ethyl, tritiated ethyl, isopropyl, deuterated isopropyl, tritiated isopropyl, tert-butyl, deuterated tert-butyl, tritiated tert-butyl, cyclopentyl, deuterated cyclopentyl, tritiated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, diphenyl ether group, methyl-substituted diphenyl ether group, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuryl, phenyl-substituted tert-butyl, xanthenone group, phenyl-substituted triazinyl, phenyl-substituted boranyl, methoxy, tert-butoxy;

[0050] The M 1 is represented by one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, diphenyl ether group, methyl-substituted diphenyl ether group, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuryl, dibenzofuryl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, phenyl-substituted amino, tert-butyl-substituted dibenzofuryl, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, xanthenone group;

[0051] The substituent for the substituent group is optionally selected from one or more of deuterium atom, chlorine atom, fluorine atom, trifluoromethyl, adamantyl, cyano, methyl, ethyl, propyl, isopropyl, tert-pentyl, tert-butyl, butyl, methoxy, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, quinoxalinyl, quinolinyl, isoquinolinyl, furyl, thienyl, indolyl, pyrrolyl, dibenzofuryl, dibenzothienyl, 9,9-dimethylfluorenyl, spirofluorene, carbazolyl, N-phenylcarbazolyl, carbazolinyl, azaphenanthryl.

[0052] In a preferred embodiment, the specific structure of the organic compound is any one of the following structures:

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061]

[0062]

[0063]

[0064] The present invention also provides an organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, wherein the organic light-emitting functional layer comprises a light-emitting layer, and the light-emitting layer contains the boron-containing organic compound having a carbazole-fluorene structure.

[0065] In a preferred embodiment, the light-emitting layer comprises a host material and a dopant material, and the dopant material contains the boron-containing organic compound having a carbazole-fluorene structure.

[0066] In a preferred embodiment, the light-emitting layer comprises a first host material, a second host material and a dopant material, at least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-containing organic compound having a carbazole-fluorene structure.

[0067] In a preferred embodiment, the light-emitting layer comprises a host material, an exciton sensitizing material and a dopant material, and the exciton sensitizing material is a metal-containing complex.

[0068] The beneficial technical effects of the present invention are as follows:

[0069] (1) When the compound of the present invention is applied to an OLED device, it can be used as a dopant material for the light-emitting layer material, 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;

[0070] (2) The compound of the present invention has a high fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%;

[0071] (3) As a doping material, the compound of the present invention introduces a TADF sensitizer as the second host, which can effectively improve the device efficiency;

[0072] (4) The spectral FWHM of the compound of the present invention is narrow, which can effectively improve the device color gamut and the device luminescence efficiency;

[0073] (5) The introduction of the carbazole-fluorene structure in the compound of the present invention can increase the molecular volume, reduce the intermolecular interaction, and reduce the efficiency roll-off caused by molecular packing;

[0074] The compound of the present invention has a narrow full width at half maximum and a high fluorescence quantum yield, and 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. Brief Description of the Drawings

[0075] Figure 1 It is a schematic structural diagram of the materials listed in the present invention applied to an OLED device;

[0076] 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 Embodiments

[0077] The present invention will be specifically described below with reference to the drawings and embodiments.

[0078] In the present invention, when describing electrodes, organic electroluminescent devices, and other structures, the orientation words such as "upper", "lower", "top", and "bottom" are only for indicating the orientation in a 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 far from the substrate is the "top" and "upper" sides.

[0079] In the present invention, substituted or unsubstituted C 6 -C 30An aryl group refers to a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dimethylfluorenyl group, a substituted or unsubstituted diphenylfluorenyl group, a substituted or unsubstituted spirofluorenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted condensed tetraphenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted m-terphenyl group, a substituted or unsubstituted group, a substituted or unsubstituted meta-terphenyl group, a substituted or unsubstituted

[0080] In the present invention, the substituted or unsubstituted C 2 -C 30 A heteroaryl group refers to a substituted or unsubstituted furyl group, a substituted or unsubstituted thienyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, a substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuryl group, a substituted or unsubstituted benzothienyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted isoquinolinyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazinyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted phenazinyl group, a substituted or unsubstituted phenothiazinyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuryl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted carbazolyl group, a combination thereof or a fused ring of the foregoing group combinations, but not limited thereto.

[0081] The C 1 -C 10 An alkyl group (including a straight-chain alkyl group and a branched-chain alkyl group) refers to a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, an isobutyl group, a sec-butyl group, a neopentyl group, a n-pentyl group, an isopentyl group, an octyl group, a heptyl group, a n-decyl group, a 1-methylpentyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 1-butylpentyl group, etc., but not limited thereto.

[0082] The C 3 -C 10 A cycloalkyl group refers to a monovalent monocyclic saturated hydrocarbon group including 3 to 10 carbon atoms as ring-forming atoms. In this article, C 4 -C 9 cycloalkyl group is preferably used, and more preferably C5 -C 8 cycloalkyl group, particularly preferably C 5 -C 7 cycloalkyl group. Non-limiting examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl, cycloheptyl, etc., but are not limited thereto.

[0083] 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 smoothnesses, 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.

[0084] 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 usually 50 - 500 nm, preferably 70 - 300 nm, and more preferably 100 - 200 nm.

[0085] 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.

[0086] In this article, the hole transport region constituting the organic electroluminescent device can be exemplified as a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0087] 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.

[0088] 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 such as fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyarylalkane derivatives, polyphenylene vinylenes and their derivatives, polythiophenes and their 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.

[0089] Furthermore, according to the requirements of device configuration, 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.

[0090] 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 a 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.

[0091] In view of the above empirical summaries, for hole-type 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.

[0092] Thus, in one embodiment of the present invention, in order to better inject holes, the hole injection layer further comprises 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.

[0093] 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, based on mass.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] 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.

[0098] The light-emitting layer may comprise 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 a boron-containing organic compound with a carbazole-fluorene structure represented by the general formula (1) of the present invention.

[0099] The light-emitting layer may comprise a single host material or a dual host material;

[0100] The dual host material comprises 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;

[0101] TADF materials refer to materials with thermally activated delayed fluorescence properties, characterized by having a small energy difference between the first singlet excited state and the first triplet excited state. Therefore, singlet excitons and triplet excitons generated can be utilized simultaneously 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.

[0102] The light-emitting layer may include a host material, an exciton sensitizing material, and a doping material;

[0103] The exciton sensitizing material refers to a material that can enable the luminescent material in the light-emitting layer to fully utilize electrochemically generated excitons, so that the light-emitting layer finally generates the emission spectrum of the sensitized material. The exciton sensitizer may perform functions such as exciton capture, exciton conversion, and exciton transfer in the electroluminescent device. In the present invention, the boron-containing organic compound containing a carbazole-fluorene structure shown in general formula (1) is used in combination with the exciton sensitizing material, which has an obvious improvement effect on problems such as device efficiency improvement, exciton annihilation in the device, and efficiency reduction.

[0104] 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.

[0105] 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.

[0106] 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.

[0107] The hole blocking layer is a layer that blocks holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the life of the device and improving the performance of the device. The hole blocking layer of the present invention can be provided above 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.

[0108] The electron transport layer can 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-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.

[0109] The electron injection layer can 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.

[0110] The second electrode can be disposed above the electron transport region. The second electrode can be a cathode. The second electrode can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the second electrode is a transmissive electrode, the second electrode can include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or their compounds or mixtures; when the second electrode is a semi-transmissive electrode or a reflective electrode, the second electrode can include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or their compounds or mixtures, but is not limited thereto. The thickness of the cathode depends on the materials used.

[0111] 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.

[0112] 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, and optionally a covering layer on a substrate. In this regard, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI can be used, but are not limited thereto. In the present invention, it is preferred to use the vacuum evaporation method 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.

[0113] Synthesis Example

[0114] 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;

[0115] Synthesis of Compound 19 in Example 1:

[0116]

[0117] Preparation of Intermediate a-1:

[0118] In a three-necked flask, under nitrogen protection, add 10 mmol of raw material A-1, 12 mmol of NaH, and 20 mL of anhydrous DMF, stir at room temperature for 1 hour, then add 10 mmol of raw material B-1, and heat to 120 °C for reaction for 3 hours. Naturally cool to room temperature, add 100 mL of water, filter and collect the precipitate. The precipitate is dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and separated and purified by silica gel column chromatography to obtain Intermediate a-1. LC-MS: Measured value: 578.11 ([M+H] + )), theoretical value: 577.08.

[0119] Preparation of Intermediate b-1:

[0120] In a three-necked flask, under nitrogen protection, add 10 mmol of raw material C-1, 12 mmol of NaH, and 20 mL of anhydrous DMF, stir at room temperature for 1 hour, then add 10 mmol of Intermediate a-1, and heat to 120 °C for reaction for 8 hours. Naturally cool to room temperature, add 100 mL of water, filter and collect the precipitate. The precipitate is dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and separated and purified by silica gel column chromatography to obtain Intermediate b-1. LC-MS: Measured value: 877.19 ([M+H]+ ), Theoretical value: 876.21.

[0121] Preparation of Compound 19:

[0122] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-1 and 10 mL of anhydrous o-dichlorobenzene were added. After cooling to -78 °C, 12 mmol of 2.5 M n-butyllithium-n-hexane solution was added dropwise. After transferring to 60 °C and reacting for 2 hours, the reaction was cooled to -42 °C, and 15 mmol of boron tribromide was added dropwise. After slowly returning to room temperature, the reaction was carried out for 3 hours. Under the condition of cooling to 0 °C, ultra-dry lithium diisopropylamide was added dropwise, and the reaction solution was heated to 180 °C and reacted for 12 hours. After cooling to room temperature, the low-boiling solvent was removed by distillation under reduced pressure, dissolved in dichloromethane, filtered, dried over anhydrous sodium sulfate and filtered to collect the filtrate, and concentrated and purified by column chromatography to obtain Compound 19. The half-peak width of Compound 19 in toluene solution (1×10 -5 M) is 24 nm, which was measured by a Horiba Fluorolog-3 series fluorescence spectrometer. 1 H NMR (400 MHz, chloroform-d): δ 7.30 - 7.76 (20H, m), 7.87 - 8.14 (10H, m), 8.22 - 8.37 (2H, m), 8.45 (1H, d), 8.82 (1H, m), 8.90 (1H, dd).

[0123] Synthesis of Compound 26 in Example 2:

[0124]

[0125] Preparation of Intermediate c-1:

[0126] Under nitrogen protection, 10 mmol of raw material D-1, 11 mmol of raw material E-1, 15 mmol of potassium carbonate, 0.5 mmol of tetrakis(triphenylphosphine)palladium, 40 mL of toluene, and 5 mL of water were added to a three-necked flask and refluxed for 12 hours. After the reaction was completed, the organic phase was collected by liquid separation, 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: 381.15 ([M+H] + ), Theoretical value: 380.10.

[0127] Preparation of Intermediate a-2:

[0128] In a three-necked flask, under nitrogen protection, add 10 mmol of raw material A-1, 12 mmol of NaH, and 20 mL of anhydrous DMF. Stir at room temperature for 1 hour, then add 10 mmol of intermediate c-1, and heat to 120 °C for reaction for 5 hours. Naturally cool to room temperature, add 100 mL of water, filter and collect the precipitate. The precipitate is dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and separated and purified by silica gel column chromatography to obtain intermediate a-2. LC-MS: Measured value: 690.27 ([M+H] + ), theoretical value: 689.21.

[0129] Preparation of intermediate b-2:

[0130] In a three-necked flask, under nitrogen protection, add 10 mmol of raw material C-2, 12 mmol of NaH, and 20 mL of anhydrous DMF. Stir at room temperature for 1 hour, then add 10 mmol of intermediate a-2, and heat to 120 °C for reaction for 3 hours. Naturally cool to room temperature, add 100 mL of water, filter and collect the precipitate. The precipitate is dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and separated and purified by silica gel column chromatography to obtain intermediate b-2. LC-MS: Measured value: 1116.43 ([M+H] + ), theoretical value: 1115.48.

[0131] Preparation of compound 26:

[0132] In a sealed pressure-resistant tube, under nitrogen protection, add 10 mmol of intermediate b-2 and 5 mL of o-dichlorobenzene. Add a n-hexane solution of 12 mmol of n-butyllithium at 0 °C, heat to 60 °C and react for 2 hours. Then add 15 mmol of boron tribromide at 0 °C, transfer to room temperature and continue to react for 4 hours. Then add 20 mmol of N,N-diisopropylethylamine to the system at 0 °C, heat to 200 °C and react for 3 hours. After the reaction is completed, reduce the pressure and concentrate the organic layer, and then purify by silica gel column chromatography to obtain compound 26. The half-peak width of compound 26 in toluene solution (1×10 -5 M) is 22 nm, which is measured by a Fluorolog-3 series fluorescence spectrometer from Horiba.

[0133] Synthesis of compound 36 in Example 3:

[0134]

[0135] Preparation of intermediate c-2:

[0136] Under nitrogen protection, 10 mmol of raw material D-2, 11 mmol of raw material E-2, 15 mmol of potassium carbonate, 0.5 mmol of tetrakis(triphenylphosphine)palladium, 40 mL of toluene, and 5 mL of water 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 c-2. LC-MS: Measured value: 353.11 ([M+H] + ), theoretical value: 352.06.

[0137] Preparation of intermediate a-3:

[0138] In a three-necked flask, under nitrogen protection, 10 mmol of raw material A-1, 12 mmol of NaH, and 20 mL of anhydrous DMF were added, and the mixture was stirred at room temperature for 1 hour. Then 10 mmol of intermediate c-2 was added, and the reaction was heated to 120 °C for 4 hours. After natural cooling to room temperature, 100 mL of water was added, and the precipitate was filtered and collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and separated and purified by silica gel column chromatography to obtain intermediate a-3. LC-MS: Measured value: 662.22 ([M+H] + ), theoretical value: 661.18.

[0139] Preparation of intermediate b-3:

[0140] In a three-necked flask, under nitrogen protection, 10 mmol of raw material C-1, 12 mmol of NaH, and 20 mL of anhydrous DMF were added, and the mixture was stirred at room temperature for 1 hour. Then 10 mmol of intermediate a-3 was added, and the reaction was heated to 120 °C for 5 hours. After natural cooling to room temperature, 100 mL of water was added, and the precipitate was filtered and collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and separated and purified by silica gel column chromatography to obtain intermediate b-3. LC-MS: Measured value: 961.35 ([M+H] + ), theoretical value: 960.31.

[0141] Preparation of compound 36:

[0142] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-3 and 5 mL of o-dichlorobenzene were added. A hexane solution of 12 mmol of n-butyllithium was added at 0 °C, the reaction 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 5 hours. Then 20 mmol of N,N-diisopropylethylamine was added to the system at 0 °C, and the reaction was heated to 200 °C and reacted 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 compound 36. Compound 36 was in a toluene solution (1×10 -5M) The full width at half maximum is 23 nm, which was measured by a Horiba Fluorolog-3 series fluorescence spectrometer. 1 1H NMR (400 MHz, chloroform-d): δ 1.52 (12H, d), 2.99 (2H, m), 7.17 - 7.71 (20H, m), 7.76 - 8.03 (8H, m), 8.20 (1H, m), 8.39 (1H, d), 8.90 - 9.13 (3H, m).

[0143] Synthesis of Compound 39 in Example 4:

[0144]

[0145]

[0146] Preparation of Intermediate d-1:

[0147] In a three-necked flask, under nitrogen protection, 10 mmol of starting material A-2, 12 mmol of NaH, and 20 mL of anhydrous DMF were added. The mixture was stirred at room temperature for 1 hour, then 10 mmol of starting material B-2 was added, and the reaction was heated to 120 °C for 2 hours. After natural cooling to room temperature, 100 mL of water was added, and the precipitate was filtered and collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to obtain Intermediate d-1. LC-MS: Measured value: 389.26 ([M+H] + )), Theoretical value: 388.19.

[0148] Preparation of Intermediate b-4:

[0149] In a three-necked flask, under nitrogen protection, 10 mmol of Intermediate d-1, 12 mmol of NaH, and 20 mL of anhydrous DMF were added. The mixture was stirred at room temperature for 1 hour, then 10 mmol of Intermediate a-3 was added, and the reaction was heated to 120 °C for 8 hours. After natural cooling to room temperature, 100 mL of water was added, and the precipitate was filtered and collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to obtain Intermediate b-4. LC-MS: Measured value: 1030.41 ([M+H] + )), Theoretical value: 1029.37.

[0150] Preparation of Compound 39:

[0151] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-4 and 5 ml of o-dichlorobenzene were added. A solution of 12 mmol of n-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 2 hours. Subsequently, 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, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 39. The half-peak width of compound 39 in toluene solution (1×10 -5 M) was 21 nm, which was measured by a Horiba Fluorolog-3 series fluorescence spectrometer. 1 1H NMR (400 MHz, chloroform-d): δ 1.27 (9H, s), 1.66 (12H, d), 2.84 (2H, dd), 7.15 (2H, dd), 7.27 - 7.79 (17H, m), 7.88 - 7.96 (5H, m), 8.11 (1H, dd), 8.22 - 8.40 (4H, m), 8.89 (1H, d), 9.12 (1H, d).

[0152] Example 5 Synthesis of Compound 46:

[0153]

[0154] Preparation of Intermediate d-2:

[0155] In a three-necked flask, under nitrogen protection, 10 mmol of raw material A-3, 12 mmol of NaH, and 20 mL of anhydrous DMF were added, and the mixture was stirred at room temperature for 1 hour. Then, 10 mmol of raw material B-2 was added, and the reaction was heated to 120 °C for 4 hours. After natural cooling to room temperature, 100 mL of water was added, and the precipitate was filtered and collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and separated and purified by silica gel column chromatography to obtain intermediate d-2. LC-MS: Measured value: 389.30 ([M + H] + ), theoretical value: 388.19.

[0156] Preparation of Intermediate a-5:

[0157] In a three-necked flask, under nitrogen protection, 10 mmol of raw material A-1, 12 mmol of NaH, and 20 mL of anhydrous DMF were added. The mixture was stirred at room temperature for 1 hour, then 10 mmol of raw material B-3 was added, and the reaction was heated to 120 °C for 8 hours. After natural cooling to room temperature, 100 mL of water was added, and the precipitate was filtered and collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to obtain intermediate a-5. LC-MS: Measured value: 558.21 ([M+H] + ), theoretical value: 557.12.

[0158] Preparation of intermediate b-5:

[0159] In a three-necked flask, under nitrogen protection, 10 mmol of intermediate d-2, 12 mmol of NaH, and 20 mL of anhydrous DMF were added. The mixture was stirred at room temperature for 0.5 hour, then 10 mmol of intermediate a-5 was added, and the reaction was heated to 120 °C for 6 hours. After natural cooling to room temperature, 100 mL of water was added, and the precipitate was filtered and collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by silica gel column chromatography to obtain intermediate b-5. LC-MS: Measured value: 926.40 ([M+H] + ), theoretical value: 925.30.

[0160] Preparation of compound 46:

[0161] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-5 and 5 mL of o-dichlorobenzene were added. A solution of 12 mmol of n-butyllithium in n-hexane was added at 0 °C, and the reaction system was heated to 60 °C and reacted for 3 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 reaction was heated to 200 °C and reacted for 4 hours. After the reaction was completed, the organic layer was depressurized and concentrated, and then purified by silica gel column chromatography to obtain compound 46. The half-peak width of compound 46 in toluene solution (1×10 -5 M) was 21 nm, which was measured by a Fluorolog-3 series fluorescence spectrometer from Horiba.

[0162] Synthesis of compound 80 in Example 6:

[0163]

[0164] Preparation of intermediate b-6:

[0165] In a three-necked flask, under nitrogen protection, add 10 mmol of raw material C-2, 12 mmol of NaH, and 20 mL of anhydrous DMF, stir at room temperature for 1 hour, then add 10 mmol of intermediate a-2, heat to 120 ° C and react for 6 hours. Naturally cool to room temperature, add 100 mL of water, filter and collect the precipitate, dissolve the precipitate with 20 mL of dichloromethane, dry and filter with anhydrous sodium sulfate, concentrate and separate and purify by silica gel column chromatography to obtain intermediate b-6. LC-MS: Measured value: 989.46 ([M+H] + ), theoretical value: 988.34.

[0166] Preparation of compound 80:

[0167] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-6 and 5 ml of o-dichlorobenzene were added. 12 mmol of n-butyl lithium in n-hexane solution was added at 0°C, the system was heated to 60°C and reacted for 2 hours, then 15 mmol of boron tribromide was added at 0°C, the system was transferred to room temperature and continued to react 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 2 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 80. Compound 80 was dissolved in toluene solution (1×10 -5 M) The half-peak width is 26 nm, measured by Horiba's Fluorolog-3 series fluorescence spectrometer.

[0168] Example 7 Synthesis of Compound 132:

[0169]

[0170] Preparation of intermediate a-6:

[0171] Under nitrogen protection, 10 mmol of raw material A-1, 10 mmol of raw material B-4, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd 2 (dba) 3 , 1.5 mmol tri-tert-butylphosphine and 20 mL anhydrous toluene were added to a three-necked flask and refluxed for 16 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-6. LC-MS: Measured value: 706.22 ([M+H] + ), theoretical value: 705.18.

[0172] Preparation of intermediate f-1:

[0173] Under nitrogen protection, 10 mmol of intermediate a-6, 10 mmol of raw material F-1, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd2 (dba) 3 , 1.5 mmol tri-tert-butylphosphine and 20 mL 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 f-1. LC-MS: Measured value: 775.42 ([M+H] + ), theoretical value: 774.37.

[0174] Preparation of intermediate b-7:

[0175] Under nitrogen protection, 10 mmol of intermediate f-1, 10 mmol of raw material E-1, 15 mmol of potassium tert-butoxide, 0.5 mmol of Pd 2 (dba) 3 , 1.5 mmol tri-tert-butylphosphine and 20 mL anhydrous toluene were added to a three-necked flask and refluxed for 18 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-7. LC-MS: Measured value: 1014.50 ([M+H] + ), theoretical value: 1013.45.

[0176] Preparation of compound 132:

[0177] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-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 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 11 hours, then 20 mmol of N,N-diisopropylethylamine was added to the system at 0°C, heated to 200°C and reacted 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 compound 132. Compound 132 was dissolved in toluene solution (1×10 -5 M) The half-peak width is 25 nm, which is measured by Horiba's Fluorolog-3 series fluorescence spectrometer. 1 H NMR (400 MHz, deuterated chloroform): δ 1.25-1.36 (27H, d), 6.61 (2H, m), 6.98-7.15 (3H, m), 7.24-7.73 (17H, m), 7.89-8.51 (9H, m).

[0178] Example 8 Synthesis of Compound 167:

[0179]

[0180]

[0181] Preparation of Intermediate a-7:

[0182] In a three-necked flask, under nitrogen protection, add 10 mmol of raw material A-4, 12 mmol of NaH, and 20 mL of anhydrous DMF. Stir at room temperature for 1 hour, then add 10 mmol of raw material B-5, and heat to 120 °C for reaction for 4 hours. Naturally cool to room temperature, add 100 mL of water, filter and collect the precipitate. The precipitate is dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and separated and purified by silica gel column chromatography to obtain Intermediate a-7. LC-MS: Measured value: 594.33 ([M+H] + ), theoretical value: 593.23.

[0183] Preparation of Intermediate P1:

[0184] In a three-necked flask, under nitrogen protection, dissolve 30 mmol of raw material M1 in dehydrated DMF (100 mL) and cool to 0 °C. Slowly add 37 mmol of NaH and stir for 30 minutes. Then add 36 mmol of tert-butyldimethylchlorosilane at one time. After stirring for 1 h, raise the reaction temperature to room temperature and continue stirring for 2 h. Add toluene and aqueous NaHCO3 solution to the reaction system, and extract the aqueous layer with toluene. Combine the organic layers, dry over anhydrous sodium sulfate and concentrate. Separate the product by silica gel column chromatography (toluene:hexane = 1:2 → 2:1 → 10:0) to obtain Intermediate P1. LC-MS: Measured value: 360.13 ([M+H]+), theoretical value: 359.07.

[0185] Preparation of Intermediate P2:

[0186] In a three-necked flask, under nitrogen protection, add 10 mmol of Intermediate P1, 12 mmol of raw material M2, and 300 mL of toluene and stir to mix. Then add 0.05 mmol of Pd2(dba)3, 0.05 mmol of P(t-Bu)3, and 30 mmol of sodium tert-butoxide, heat to 110 °C, and reflux for 24 hours; naturally cool to room temperature, filter, and rotary evaporate the filtrate under reduced pressure. The crude product is purified by silica gel column chromatography (eluent: hexane / CH2Cl2 = 5 / 1) to obtain the target product Intermediate P2. LC-MS: Measured value: 561.32 ([M+H]+), theoretical value: 560.36.

[0187] Preparation of Raw Material C-2:

[0188] In a three-necked flask, under nitrogen protection, 16 mmol of intermediate P2 was dissolved in 100 mL of toluene, then 25 mL of TBAF (1 M THF solution) was added, and the mixture was stirred for 15 minutes. An aqueous solution of NH4Cl was added to the mixture, and the organic layer was separated. The aqueous layer was extracted with toluene. The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated. The mixture was recrystallized with n-hexane and toluene to obtain raw material C-2. LC-MS: Measured value: 447.39 ([M+H]+), theoretical value: 446.27.

[0189] Preparation of intermediate b-8:

[0190] In a three-necked flask, under nitrogen protection, 10 mmol of raw material C-2, 12 mmol of NaH, and 20 mL of anhydrous DMF were added. The mixture was stirred at room temperature for 0.5 hour, then 10 mmol of intermediate a-7 was added, and the reaction was carried out at 120 °C for 2 hours. It was naturally cooled to room temperature, 100 mL of water was added, the precipitate was filtered and collected. The precipitate was dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and separated and purified by silica gel column chromatography to obtain intermediate b-8. LC-MS: Measured value: 1020.41 ([M+H] + )), theoretical value: 1019.49.

[0191] Preparation of compound 167:

[0192] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-8 and 5 mL of o-dichlorobenzene were added. A hexane solution of 12 mmol of tert-butyllithium was added at 0 °C, the reaction system was heated to 60 °C and reacted for 1 hour. Then, 15 mmol of boron tribromide was added at 0 °C, and 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, and the reaction was carried out at 200 °C for 2 hours. After the reaction was completed, the organic layer was decompressed and concentrated, and then purified by silica gel column chromatography to obtain compound 167. The half-peak width of compound 167 in toluene solution (1×10 -5 M) is 22 nm, which was measured by a Fluorolog-3 series fluorescence spectrometer from Horiba.

[0193] Synthesis of compound 168 in Example 9:

[0194]

[0195] Preparation of intermediate a-8:

[0196] In a three-necked flask, under nitrogen protection, add 10 mmol of raw material A-4, 12 mmol of NaH, and 20 mL of anhydrous DMF. Stir at room temperature for 1 hour, then add 10 mmol of intermediate c-1, and heat to 120 °C for reaction for 2 hours. Naturally cool to room temperature, add 100 mL of water, filter and collect the precipitate. The precipitate is dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and separated and purified by silica gel column chromatography to obtain intermediate a-8. LC-MS: Measured value: 692.20 ([M+H] + ), theoretical value: 691.22.

[0197] Preparation of intermediate b-9:

[0198] In a three-necked flask, under nitrogen protection, add 10 mmol of raw material C-1, 12 mmol of NaH, and 20 mL of anhydrous DMF. Stir at room temperature for 0.5 hour, then add 10 mmol of intermediate a-8, and heat to 120 °C for reaction for 3 hours. Naturally cool to room temperature, add 100 mL of water, filter and collect the precipitate. The precipitate is dissolved in 20 mL of dichloromethane, dried over anhydrous sodium sulfate, filtered, concentrated, and separated and purified by silica gel column chromatography to obtain intermediate b-9. LC-MS: Measured value: 991.33 ([M+H] + ), theoretical value: 990.35.

[0199] Preparation of compound 168:

[0200] In a sealed pressure-resistant tube, under nitrogen protection, add 10 mmol of intermediate b-9 and 5 mL of o-dichlorobenzene. Add a n-hexane solution of 12 mmol of n-butyllithium at 0 °C, heat the system to 60 °C and react for 1 hour. Then add 15 mmol of boron tribromide at 0 °C, transfer to room temperature and continue to react for 2 hours. Then add 20 mmol of N,N-diisopropylethylamine to the system at 0 °C, heat to 200 °C and react for 2 hours. After the reaction is completed, reduce the pressure and concentrate the organic layer, and then purify by silica gel column chromatography to obtain compound 168. The half-peak width of compound 168 in toluene solution (1×10 -5 M) is 23 nm, which is measured by a Fluorolog-3 series fluorescence spectrometer from Horiba. 1 1H NMR (400 MHz, chloroform-d): δ 1.75 (18H, s), 7.12 - 7.36 (11H, m), 7.45 - 7.79 (11H, m), 7.82 - 8.15 (8H, m), 8.24 - 8.33 (2H, m), 8.41 (1H, d), 8.92 - 9.32 (2H, m).

[0201] Synthesis of compound 213 in Example 10:

[0202]

[0203] Preparation of Intermediate b-10:

[0204] In a three-necked flask, under nitrogen protection, add 10 mmol of Intermediate d-1, 12 mmol of NaH, and 20 mL of anhydrous DMF. Stir at room temperature for 0.5 hour, then add 10 mmol of Intermediate a-8, and heat to 120 °C for reaction for 3 hours. Naturally cool to room temperature, add 100 mL of water, filter and collect the precipitate. Dissolve the precipitate in 20 mL of dichloromethane, dry over anhydrous sodium sulfate, filter, concentrate, and purify by silica gel column chromatography to obtain Intermediate b-10. LC-MS: Measured value: 1060.44 ([M+H] + ), theoretical value: 1059.41.

[0205] Preparation of Compound 213:

[0206] In a sealed pressure-resistant tube, under nitrogen protection, add 10 mmol of Intermediate b-10 and 5 mL of o-dichlorobenzene. Add a n-hexane solution of 12 mmol of n-butyllithium at 0 °C, heat the system to 60 °C and react for 2 hours. Then add 15 mmol of boron tribromide at 0 °C, transfer to room temperature and continue to react for 2 hours. Then add 20 mmol of N,N-diisopropylethylamine to the system at 0 °C, heat to 200 °C and react for 3 hours. After the reaction is completed, reduce the pressure and concentrate the organic layer, and then purify by silica gel column chromatography to obtain Compound 213. The half-peak width of Compound 213 in toluene solution (1×10 -5 M) is 21 nm, which is measured by a Horiba Fluorolog-3 series fluorescence spectrometer. 1 1H NMR (400 MHz, chloroform-d): δ 1.43 (9H, s), 1.71 (18H, s), 7.11 - 7.40 (13H, m), 7.45 - 7.82 (7H, m), 7.91 - 8.15 (8H, m), 8.25 - 8.58 (5H, m).

[0207] The structural characterizations of the compounds obtained in each example are shown in Table 1

[0208] Table 1

[0209]

[0210] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 1-10 and Device Comparative Examples 1-3. The manufacturing processes of the devices in Device Examples 2-10 and Device Comparative Examples 1-3 of the present invention 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 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 2-1 and 3 respectively:

[0211] Device Example 1

[0212] 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 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, 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 19 is used as a doping material. The mass ratio of GH-1, GH-2, and Compound 19 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 vacuum-evaporated 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 vacuum-evaporated with a mass ratio of ET-1 and Liq of 1:1 and 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.

[0213] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 11-20 and Device Comparative Examples 4-6. The manufacturing processes of the devices in Device Examples 12-20 and Device Comparative Examples 4-6 of the present invention are exactly the same as those of Device Example 11, 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:

[0214] Device Embodiment 11

[0215] 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 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 the host materials, GD-1 is used as the first doping material, and compound 19 is used as the second doping material. The mass ratio of GH-1, GH-2, GD-1, and compound 19 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.

[0216] The molecular structural formulas of the related materials are as follows:

[0217]

[0218]

[0219] After the OLED light-emitting device is completed as described above, the anode and the cathode are connected with a known drive circuit, and the current efficiency, external quantum efficiency, and the lifetime of the device are measured. The device embodiments 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.

[0220] Table 2-1

[0221]

[0222]

[0223] Table 2-2

[0224]

[0225]

[0226] Table 3

[0227]

[0228] 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 from System Technology Research Co., Ltd. of Japan; LT95 refers to the time it takes for the device luminance to decay to 95%; all data were measured at 10 mA / cm 2 under the test.

[0229] From the device data results in Table 3, it can be seen that compared with the comparative compounds ref-1, ref-2, and ref-3, the emission peak of the compound of the present invention is between 510 and 550 nm, and it can well achieve the effect of green emission; compared with device comparative examples 1-6, for the organic light-emitting device of the present invention, whether in a single-doping system or a double-doping system, the current efficiency and lifetime of the device have been greatly improved compared to the OLED devices of known materials; when using an exciton sensitizing material as the first dopant, the device efficiency is significantly improved compared to the single-doping case.

[0230] 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 replacements, 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 with a carbazole-fluorene structure, characterized in that, the structure of the organic compound is shown as any one of general formula (10), general formula (11), general formula (13), general formula (23) - general formula (25): In general formula (10), general formula (11), general formula (13), general formula (23) - general formula (25), Z each occurrence, the same or different, represents C-R; Each occurrence of R, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group; Z 1 、Z 2 、Z 3 are each independently represented as C-R a 、C-R b 、C-R c ; R a 、R b 、R c each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a phenyl-substituted amino group, a tert-butylphenyl-substituted amino group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group; The substituents for the substituting groups are each independently selected from one or more of a deuterium atom, a halogen atom, an alkyl group having C 1 to C 10 , a cycloalkyl group having C 3 to C 10 , and an aryl group having C 6 to C 30 ; The heteroatom in the heteroaryl group is arbitrarily selected from one of O, S, N, and Si.

2. A boron-containing organic compound with a carbazole-fluorene structure, characterized in that, the structure of the organic compound is shown as any one of general formula (30) - general formula (31), general formula (33) - general formula (35), general formula (37), general formula (39), general formula (40): In general formula (30) - general formula (31), general formula (33) - general formula (35), general formula (37), general formula (39), general formula (40), Z each occurrence, the same or different, represents C-R; Each occurrence of R, which may be the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group; R b is represented by a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted C 1 -C 10 -C alkyl, a substituted or unsubstituted C 3 -C 10 -C cycloalkyl, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a substituted or unsubstituted C 6 -C 30 -C aryl, a substituted or unsubstituted C 2 -C 30 -C heteroaryl; The substituents for the substituting groups are each independently selected from one or more of a deuterium atom, a halogen atom, an alkyl group having C 1 to C 10 , a cycloalkyl group having C 3 to C 10 , and an aryl group having C 6 to C 30 ; The heteroatom in the heteroaryl group is arbitrarily selected from one of O, S, N, and Si.

3. A boron-containing organic compound with a carbazole-fluorene structure, characterized in that, the structure of the organic compound is shown as any one of general formula (41) - general formula (46): In general formula (41) - general formula (46), Z each occurrence, the same or different, represents C-R; Each occurrence of R, which is the same or different, represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted C 1 ~C 10 alkyl group, a substituted or unsubstituted C 3 ~C 10 cycloalkyl group, a phenyl-substituted amino group, a tert-butylphenyl-substituted amino group, a substituted or unsubstituted C 6 ~C 30 aryl group, a substituted or unsubstituted C 2 ~C 30 heteroaryl group; Z 1 、Z 2 、Z 3 are each independently represented as C-R a 、C-R b 、C-R c ; R a 、R b 、R c each independently represents a hydrogen atom, a deuterium atom, a halogen atom, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 2 -C 30 heteroaryl group; R 3 represents one of substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted C 2 -C 30 heteroaryl; The Ar 1 represents one of substituted or unsubstituted C 3 -C 10 cycloalkyl, substituted or unsubstituted C 6 -C 30 aryl, substituted or unsubstituted C 2 -C 30 heteroaryl; The substituents for the substituting groups are each independently selected from one or more of a deuterium atom, a tritium atom, a halogen atom, an alkyl group having C 1 to C 10 , a cycloalkyl group having C 3 to C 10 , and an aryl group having C 6 to C 30 ; The heteroatom in the heteroaryl group is arbitrarily selected from one of O, S, N, and Si.

4. The boron-containing organic compound with a carbazole-fluorene structure according to claim 1, characterized in that, Said R, R a , R b , R c are represented in the following structure:

5. The boron-containing organic compound with a carbazole-fluorene structure according to claim 2, characterized in that, The R, R b are represented in the following structure:

6. The boron-containing organic compound with a carbazole-fluorene structure according to claim 3, characterized in that, Said R, R a , R b , R c are represented in the following structure: The said R 3 , Ar 1 is represented in the following structure:

7. The boron-containing organic compound with a carbazole-fluorene structure according to claim 1, characterized in that, The R, R a , R b , R c each independently represents a hydrogen atom, a deuterium atom, a halogen atom, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, an anthracenyl group, a 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 oxanthrone group, a phenyl-substituted triazinyl group; The substituents for the substitution group are arbitrarily selected from one or more of deuterium atom, chlorine atom, fluorine atom, adamantyl group, methyl group, ethyl group, propyl group, isopropyl group, tert-pentyl group, tert-butyl group, butyl group, phenyl group, biphenyl group, naphthyl group, anthracenyl group, and phenanthryl group.

8. The boron-containing organic compound with a carbazole-fluorene structure according to claim 2, characterized in that, The R and R b each independently represents a hydrogen atom, a deuterium atom, a halogen atom, an adamantyl group, a methyl group, a deuterated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, an isopropyl group, a deuterated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a biphenyl group, a deuterated biphenyl group, a terphenyl group, a deuterated terphenyl group, a naphthyl group, an anthracenyl group, a 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 oxanthrone group, a phenyl-substituted triazinyl group; The substituents for the substitution group are arbitrarily selected from one or more of deuterium atom, chlorine atom, fluorine atom, adamantyl group, methyl group, ethyl group, propyl group, isopropyl group, tert-pentyl group, tert-butyl group, butyl group, phenyl group, biphenyl group, naphthyl group, anthracenyl group, and phenanthryl group.

9. The boron-containing organic compound with a carbazole-fluorene structure according to claim 3, characterized in that, Said R, R a , R b , R c are each independently represented by a hydrogen atom, deuterium atom, halogen atom, adamantyl group, methyl group, deuterated methyl group, trifluoromethyl group, ethyl group, deuterated ethyl group, isopropyl group, deuterated isopropyl group, tert-butyl group, deuterated tert-butyl group, cyclopentyl group, deuterated cyclopentyl group, methyl-substituted cyclopentyl group, cyclohexyl group, phenyl group, deuterated phenyl group, biphenyl group, deuterated biphenyl group, terphenyl group, deuterated terphenyl group, naphthyl group, anthracenyl group, phenanthryl group, pyridyl group, phenyl-substituted pyridyl group, quinolinyl group, furyl group, thienyl group, benzofuryl group, dibenzofuryl group, dibenzothienyl group, carbazolyl group, N-phenylcarbazolyl group, 9,9-dimethylfluorenyl group, spirofluorene group, methyl-substituted phenyl group, ethyl-substituted phenyl group, isopropyl-substituted phenyl group, tert-butyl-substituted phenyl group, methyl-substituted biphenyl group, ethyl-substituted biphenyl group, isopropyl-substituted biphenyl group, tert-butyl-substituted biphenyl group, deuterated methyl-substituted phenyl group, deuterated ethyl-substituted phenyl group, deuterated isopropyl-substituted phenyl group, deuterated tert-butyl-substituted phenyl group, deuterated methyl-substituted biphenyl group, deuterated ethyl-substituted biphenyl group, deuterated isopropyl-substituted biphenyl group, deuterated tert-butyl-substituted biphenyl group, phenyl-substituted amino group, tert-butylbenzene-substituted amino group, tert-butyl-substituted dibenzofuryl group, phenyl-substituted tert-butyl group, xanthenone group, phenyl-substituted triazinyl group; The R 3 , Ar 1 are each independently represented by one of adamantyl, cyclopentyl, deuterated cyclopentyl, methyl-substituted cyclopentyl, cyclohexyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthryl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-dimethylfluorenyl, spirofluorene, methyl-substituted phenyl, ethyl-substituted phenyl, isopropyl-substituted phenyl, tert-butyl-substituted phenyl, methyl-substituted biphenyl, ethyl-substituted biphenyl, isopropyl-substituted biphenyl, tert-butyl-substituted biphenyl, deuterated methyl-substituted phenyl, deuterated ethyl-substituted phenyl, deuterated isopropyl-substituted phenyl, deuterated tert-butyl-substituted phenyl, deuterated methyl-substituted biphenyl, deuterated ethyl-substituted biphenyl, deuterated isopropyl-substituted biphenyl, deuterated tert-butyl-substituted biphenyl, tert-butyl-substituted dibenzofuranyl, xanthenone, phenyl-substituted triazinyl; The substituents for the substitution group are arbitrarily selected from one or more of deuterium atom, chlorine atom, fluorine atom, adamantyl group, methyl group, ethyl group, propyl group, isopropyl group, tert-pentyl group, tert-butyl group, butyl group, phenyl group, biphenyl group, naphthyl group, anthracenyl group, and phenanthryl group.

10. A boron-containing organic compound with a carbazole-fluorene structure, characterized in that, the specific structure of the organic compound is any one of the following structures:

11. An organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, the organic light-emitting functional layer comprising a light-emitting layer, Characterized in that, the light-emitting layer contains the boron-containing organic compound with a carbazole-fluorene structure according to any one of claims 1-10.

12. The organic electroluminescent device according to claim 11, Characterized in that, the light-emitting layer comprises a host material and a dopant material, and the dopant material contains the boron-containing organic compound with a carbazole-fluorene structure according to any one of claims 1-10.

13. The organic electroluminescent device according to claim 11, wherein the light-emitting layer comprises a first host material, a second host material and a dopant material, Characterized in that, at least one of the first host material and the second host material is a TADF material, and the dopant material is the boron-containing organic compound with a carbazole-fluorene structure according to any one of claims 1-10.

14. The organic electroluminescent device according to claim 12, wherein the light-emitting layer comprises a host material, an exciton sensitizing material and a dopant material, Characterized in that: the exciton sensitizing material is a metal element-containing complex.

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