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 technical field of semiconductors. The structure of the organic compound of the present invention is shown in the general formula (1). The compound of the present invention has a narrow full width at half maximum, a high fluorescence quantum yield, and a suitable emission color. When 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 of the light emission of the device, improving the current efficiency and the device life.

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] Restricted by early technology, 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% at most), and the external quantum efficiency is generally lower than 5%, showing a significant gap compared with the efficiency of phosphorescent devices. Due to the strong spin-orbit coupling of heavy atom centers, phosphorescent materials can enhance intersystem crossing, effectively utilize singlet excitons and triplet excitons formed by electrical excitation for luminescence, and enable 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 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 by simple methods. Therefore, to meet higher color rendering standards, it is of great significance to study efficient green fluorescent doping materials with narrow full width at half maximum.

[0004] In addition, the TADF sensitized fluorescence technology (TSF) combines TADF materials with fluorescent doping materials. Using TADF materials as exciton sensitization media, triplet excitons formed by electrical excitation are converted into singlet excitons, and the energy is transferred to the fluorescent doping materials through long-range energy transfer of singlet excitons. Similarly, the internal quantum efficiency of the device can reach 100%. This technology can make up for the deficiency of low exciton utilization rate of fluorescent doping materials and effectively utilize 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 to thermally activated delayed fluorescence (TADF) sensitized fluorescence technology, devices with high efficiency and narrow FWHM emission can be fabricated. For example, in CN 107507921 A and CN110492006 A, a luminescent layer combination technology is disclosed, which uses a TADF material with the energy difference between the lowest singlet state and the lowest triplet state 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 that of phosphorescence and a relatively narrow FWHM. Therefore, developing TADF sensitized fluorescence technology 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 and an organic electroluminescent device prepared therefrom. The compound of the present invention has a narrow FWHM and a high fluorescence quantum yield, and can be used as a green light dopant material for the luminescent layer of an organic electroluminescent device, thereby improving the color purity, efficiency, and lifespan of the device.

[0007] The technical solution of the present invention is as follows:

[0008] A boron-containing organic compound, the structure of the boron-containing organic compound is shown in general formula (1):

[0009]

[0010] In general formula (1), Z represents C-R1;

[0011] Each occurrence of R1 represents the same or different hydrogen atom, deuterium atom, tritium atom, halogen atom, substituted or unsubstituted C1-C 10 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 alkoxy, substituted or unsubstituted C5-C 10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 heteroaryl;

[0012] Two adjacent R1s can also be connected to form a ring;

[0013] R2 represents substituted or unsubstituted C1-C 10 alkyl, substituted or unsubstituted C2-C 10 alkenyl, substituted or unsubstituted C3-C10 A cycloalkyl group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0014] R2 and the adjacent R1 may also be connected to form a ring;

[0015] The substituents for the substituents are each independently selected from a deuterium atom, a tritium atom, a halogen atom, 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 a combination thereof;

[0016] M1 and M2 each represent 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.

[0017] Preferably, the structure of the organic compound is represented by General Formula (2) or General Formula (3):

[0018]

[0019] In General Formula (2) and General Formula (3), the meanings of M1, M2, and R2 are the same as defined above;

[0020] M3, M4, and M5 each represent 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.

[0021] More preferably, the structure of the organic compound is represented by any one of General Formulas (4) to (21):

[0022]

[0023] In General Formulas (4) to (21), the meanings of Z, M4, and R2 are the same as defined above;

[0024] X represents O, S, Se, N(R3), C(R4)(R5), or Si(R6)(R7);

[0025] R3 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 30One of aryl, substituted or unsubstituted C2-C 30 heteroaryl; R4, R5, R6, and R7 are each independently represented as a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, substituted or unsubstituted C1-C 10 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 alkoxy, substituted or unsubstituted C5-C 10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 heteroaryl;

[0026] The substituents for the substituents of the group are each independently selected from a deuterium atom, a tritium atom, a halogen atom, C1-C 10 alkyl, C3-C 10 cycloalkyl, C6-C 30 aryl, C2-C 30 heteroaryl, or one or more thereof.

[0027] More preferably, the structure of the organic compound is represented by any one of general formula (4-1) to general formula (12-4):

[0028]

[0029]

[0030] In general formula (4-1) to general formula (12-4), the definitions of Z, R1-R7, and X are the same as those defined above.

[0031] Preferably, the structure of the organic compound is represented by any one of general formula (A-1) to general formula (A-12):

[0032]

[0033] In general formula (A-1) to general formula (A-12), Z is represented as C-R1;

[0034] Each occurrence of R1 is the same or different and is represented as a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, substituted or unsubstituted C1-C 10 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 alkoxy, substituted or unsubstituted C5-C 10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 heteroaryl;

[0035] X is represented as O, S, Se, N(R3), C(R4)(R5) or Si(R6)(R7);

[0036] R3 is represented as substituted or unsubstituted C1-C 10 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 heteroaryl;

[0037] R4, R5, R6, R7 are each independently represented as a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, substituted or unsubstituted C1-C 10 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 alkoxy, substituted or unsubstituted C5-C 10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 heteroaryl;

[0038] R a 、R b 、R c are each independently represented as a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, substituted or unsubstituted C1-C 10 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 alkoxy, substituted or unsubstituted C5-C 10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 heteroaryl;

[0039] The substituents for the substituted groups are each independently selected from a deuterium atom, a tritium atom, a halogen atom, C1-C 10 alkyl, C3-C 10 cycloalkyl, C6-C 30 aryl, C2-C 30 heteroaryl, one or more of them.

[0040] In a preferred embodiment, each occurrence of R1, which may be the same or different, represents 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 group, an oxanthrone group, a phenyl-substituted triazinyl group, a phenyl-substituted boranyl group, a methoxy group, or a tert-butoxy group.

[0041] Preferred embodiment, R2 is 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, xanthone group, phenyl-substituted triazine group, phenyl-substituted borane group, methoxy, tert-butoxy.

[0042] Preferred embodiment, R3-R7 are each independently represented by one of methyl, ethyl, propyl, phenyl, deuterated phenyl, tritiated phenyl, biphenyl, deuterated biphenyl, tritiated biphenyl, terphenyl, deuterated terphenyl, tritiated terphenyl, 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, xanthone group, phenyl-substituted triazine group.

[0043] Preferred embodiment, the R a 、R b 、R cIndependently 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 group, an xanthone group, a phenyl-substituted triazine group, a phenyl-substituted boranyl group, a methoxy group, a tert-butoxy group, respectively.

[0044] Further preferably, the specific structure of the boron-containing organic compound is any one of the following structures:

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061] An organic electroluminescent device includes a cathode and an anode, and an organic light-emitting functional layer therebetween. The organic light-emitting functional layer includes a light-emitting layer, and the light-emitting layer contains the boron-containing organic compound described above.

[0062] Preferably, the light-emitting layer contains a host material and a doping material, and the doping material contains the boron-containing organic compound described above.

[0063] More preferably, the light-emitting layer contains a first host material, a second host material and a doping material. At least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing organic compound described above.

[0064] Preferably, the light-emitting layer contains a host material, an exciton sensitizing material and a doping material. The exciton sensitizing material is a metal element-containing complex, and the doping material is the boron-containing organic compound described above.

[0065] The beneficial technical effects of the present invention are as follows:

[0066] (1) The compound of the present invention is applied to an OLED device and can be used as a doping material for a light-emitting layer material. 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;

[0067] (2) The compound of the present invention as a doping material has a high fluorescence quantum efficiency, and the fluorescence quantum efficiency of the material is close to 100%;

[0068] (3) The compound of the present invention as a doping material, introducing a TADF sensitizer as the second host, can effectively improve the device efficiency;

[0069] (4) The spectral FWHM of the compound of the present invention is narrow, which can effectively improve the device color gamut and the light-emitting efficiency of the device;

[0070] (5) The evaporation decomposition temperature of the compound of the present invention is high, which can inhibit the evaporation decomposition of the material and effectively improve the device life. Description of the Drawings

[0071] Figure 1 Schematic structural diagram of the materials listed in the present invention applied to an OLED device;

[0072] 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. Specific embodiments

[0073] The present invention will be further described below in conjunction with the accompanying drawings and specific embodiments, but it is not limited to the present invention.

[0074] The following embodiments are intended to better explain the present invention, but the scope of the present invention is not limited thereto.

[0075] 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;

[0076] Synthesis of Compound 8 in Example 1:

[0077]

[0078] Under nitrogen protection, 10 mmol of raw material A-1, 10 mmol of N-chlorosuccinimide (NCS), 20 mL of acetonitrile, and 1 mmol of thiourea were added to a three-necked flask and stirred at room temperature for 2 hours. After the reaction was completed, the reaction solution was concentrated, and the intermediate a-1 was obtained by column chromatography. LC-MS: Measured value: 208.13 ([M+H] + )), Theoretical value: 207.08. 1 1H NMR (500 MHz, deuterated chloroform) δ 7.5 (d, 1H), 7.6 (d, 1H), 7.2 (d, 1H), 7.1 (dd, 1H), 5.1 (s, 1H), 1.5 (s, 9H).

[0079] Under nitrogen protection, 10 mmol of intermediate a-1, 10 mmol of raw material B-1, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6, and 70 mL of dichlorobenzene were added to a three-necked flask and refluxed for 11 hours. After the reaction was completed, the organic layer was depressurized and concentrated, and then purified by silica gel column chromatography to obtain intermediate b-1. LC-MS: Measured value: 334.17 ([M+H] + )), Theoretical value: 333.13.

[0080] Under nitrogen protection, 10 mmol of intermediate b-1, 10 mmol of raw material C-1, 20 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4, 50 mL of tetrahydrofuran and 5 mL of water were added to a three-necked flask, and the mixture was refluxed for 10 hours. After the reaction, the organic phase was separated 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: 577.31 ([M+H] + ), theoretical value: 576.35.

[0081] Under nitrogen protection, 10 mmol of intermediate c-1 and 5 ml of o-dichlorobenzene were added to a pressure-resistant sealed tube. A n-hexane solution of 12 mmol of n-butyllithium 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, 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 mixture was heated to 200 °C and reacted for 5 hours. After the reaction, the organic layer was concentrated under reduced pressure, and then purified by silica gel column chromatography to obtain compound 8.

[0082] Synthesis of compound 30 in Example 2:

[0083]

[0084] Under nitrogen protection, 10 mmol of intermediate b-1, 10 mmol of raw material A-2, 20 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4, 50 mL of tetrahydrofuran and 5 mL of water were added to a three-necked flask, and the mixture was refluxed for 10 hours. After the reaction, the organic phase was separated by liquid separation, 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: 579.32 ([M+H] + ), theoretical value: 578.37

[0085] Under nitrogen protection, 10 mmol of intermediate a-2 and 5 ml of o-dichlorobenzene were added to a pressure-resistant sealed tube. A n-hexane solution of 12 mmol of n-butyllithium 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, and the reaction was continued at room temperature for 12 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 2 hours. After the reaction, the organic layer was concentrated under reduced pressure, and then purified by silica gel column chromatography to obtain compound 30.

[0086] Synthesis of compound 74 in Example 3:

[0087]

[0088] Under nitrogen protection, 10 mmol of raw material A-3, 10 mmol of raw material B-3, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6 and 70 mL of dichlorobenzene were added to a three-necked flask, and the mixture was refluxed for 22 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: 344.09 ([M+H] + ), theoretical value: 343.06.

[0089] Under nitrogen protection, 10 mmol of intermediate a-3, 10 mmol of bis(pinacolato)diboron, 5 mmol of potassium acetate, 0.1 mmol of Pd(dppf)Cl2, and 30 ml of 1,4-dioxane were added to a three-necked flask, and the mixture was refluxed for 16 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-3. LC-MS: Measured value: 392.25 ([M+H] + ), theoretical value: 391.23.

[0090] Under nitrogen protection, 10 mmol of intermediate b-1, 10 mmol of intermediate b-3, 20 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4, 50 mL of tetrahydrofuran and 5 mL of water were added to a three-necked flask, and the mixture was refluxed for 10 hours. After the reaction was completed, the organic phase was separated and collected, 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: 563.22 ([M+H] + ), theoretical value: 562.30.

[0091] Under nitrogen protection, 10 mmol of intermediate c-3 and 5 ml of o-dichlorobenzene were added to a pressure-resistant sealed tube. A hexane solution of 12 mmol of n-butyllithium 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, 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 4 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 74.

[0092] Synthesis of compound 96 in Example 4:

[0093]

[0094] Under nitrogen protection, 10 mmol of raw material A-4, 10 mmol of raw material B-3, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6 and 70 mL of dichlorobenzene were added to a three-necked flask, and the mixture was refluxed for 48 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: 360.09 ([M+H] + ), theoretical value: 359.03.

[0095] Under nitrogen protection, 10 mmol of intermediate a-4, 10 mmol of bis(pinacolato)diboron, 5 mmol of potassium acetate, 0.1 mmol of Pd(dppf)Cl2, and 30 mL of 1,4-dioxane were added to a three-necked flask, and the mixture was refluxed for 48 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-4. LC-MS: Measured value: 408.25 ([M+H] + ), theoretical value: 407.21.

[0096] Under nitrogen protection, 10 mmol of intermediate b-1, 10 mmol of intermediate b-4, 20 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4, 50 mL of tetrahydrofuran and 5 mL of water were added to a three-necked flask, and the mixture was refluxed for 12 hours. After the reaction, the organic phase was separated and collected, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-4. LC-MS: Measured value: 579.24 ([M+H] + ), theoretical value: 578.28.

[0097] Under nitrogen protection, 10 mmol of intermediate c-4 and 5 mL of o-dichlorobenzene were added to a pressure-resistant sealed tube. 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 1 hour, then 15 mmol of boron tribromide was added at 0 °C, and 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, 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 96.

[0098] Example 5 Synthesis of Compound 118:

[0099]

[0100] Under nitrogen protection, 10 mmol of raw material A-5, 10 mmol of raw material B-3, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6 and 70 mL of dichlorobenzene were added to a three-necked flask, and the mixture was refluxed for 24 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-5. LC-MS: Measured value: 360.08 ([M+H] + ), theoretical value: 359.03.

[0101] Under nitrogen protection, 10 mmol of intermediate a-5, 10 mmol of bis(pinacolato)diboron, 5 mmol of potassium acetate, 0.1 mmol of Pd(dppf)Cl2, and 30 ml of 1,4-dioxane were added to a three-necked flask, and the mixture was 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 b-5. LC-MS: Measured value: 408.27 ([M+H] + ), theoretical value: 407.21.

[0102] Under nitrogen protection, 10 mmol of intermediate b-1, 10 mmol of intermediate b-5, 20 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4, 50 mL of tetrahydrofuran and 5 mL of water were added to a three-necked flask, and the mixture was refluxed for 10 hours. After the reaction was completed, the organic phase was separated by liquid separation, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-5. LC-MS: Measured value: 579.23 ([M+H] + ), theoretical value: 578.28.

[0103] Under nitrogen protection, 10 mmol of intermediate c-5 and 5 ml of o-dichlorobenzene were added to a pressure-resistant sealed tube. A n-hexane solution of 12 mmol of n-butyllithium was added at 0 °C, the system was heated to 60 °C and reacted for 2.5 hours. Then, 15 mmol of boron tribromide was added at 0 °C, and the reaction was continued at room temperature for 2.5 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 3 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 118.

[0104] Example 6 Synthesis of Compound 140:

[0105]

[0106] Under nitrogen protection, 10 mmol of raw material A-6, 10 mmol of raw material B-3, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6 and 70 mL of dichlorobenzene were added to a three-necked flask, and the mixture was refluxed for 48 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-6. LC-MS: Measured value: 344.01 ([M+H] + ), theoretical value: 343.06.

[0107] Under nitrogen protection, 10 mmol of intermediate a-6, 10 mmol of bis(pinacolato)diboron, 5 mmol of potassium acetate, 0.1 mmol of Pd(dppf)Cl2, and 30 ml of 1,4-dioxane were added to a three-necked flask, and the mixture was 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 b-6. LC-MS: Measured value: 392.26 ([M+H] + ), theoretical value: 391.23.

[0108] Under nitrogen protection, 10 mmol of intermediate b-1, 10 mmol of intermediate b-6, 20 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4, 50 mL of tetrahydrofuran and 5 mL of water were added to a three-necked flask, and the mixture was 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-6. LC-MS: Measured value: 563.32 ([M+H] + ), theoretical value: 562.30.

[0109] Under nitrogen protection, 10 mmol of intermediate c-6 and 5 ml of o-dichlorobenzene were added to a pressure-resistant sealed tube. A n-hexane solution of 12 mmol of n-butyllithium was added at 0 °C, the reaction system was heated to 60 °C and reacted for 2.5 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 concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 140.

[0110] Synthesis of compound 161 in Example 7:

[0111]

[0112] Under nitrogen protection, 10 mmol of intermediate a-1, 10 mmol of raw material B-7, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6 and 70 mL of dichlorobenzene were added to a three-necked flask, and the mixture was refluxed for 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-7. LC-MS: Measured value: 384.20 ([M+H] + ), theoretical value: 383.14.

[0113] Under nitrogen protection, 10 mmol of intermediate a-7, 10 mmol of raw material C-1, 20 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4, 50 mL of tetrahydrofuran and 5 mL of water were added to a three-necked flask, and the mixture was refluxed for 8 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 b-7. LC-MS: Measured value: 627.31 ([M+H] + ), theoretical value: 626.37.

[0114] In a pressure-resistant sealed tube, under nitrogen protection, 10 mmol of intermediate b-7 and 5 ml of o-dichlorobenzene were added. A n-hexane solution of 12 mmol of n-butyllithium was added at 0 °C, the system was heated to 60 °C and reacted for 2.5 hours. 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 mixture was heated to 200 °C and reacted for 4 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 161.

[0115] Synthesis of Compound 224 in Example 8:

[0116]

[0117] Under nitrogen protection, 10 mmol of intermediate a-1, 10 mmol of raw material B-8, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6 and 70 mL of dichlorobenzene were added to a three-necked flask, and the mixture was refluxed for 48 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-8. LC-MS: Measured value: 384.19 ([M+H] + ), theoretical value: 383.14.

[0118] Under nitrogen protection, 10 mmol of intermediate a-8, 10 mmol of raw material C-1, 20 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4, 50 mL of tetrahydrofuran and 5 mL of water were added to a three-necked flask, and the mixture was refluxed for 6 hours. After the reaction, the organic phase was separated by liquid separation, the organic layer was concentrated under reduced pressure, and then purified by silica gel column chromatography to obtain intermediate b-8. LC-MS: Measured value: 627.32 ([M+H] + ), theoretical value: 626.37.

[0119] Under nitrogen protection, 10 mmol of intermediate b-8 and 5 ml of o-dichlorobenzene were added to a pressure-resistant sealed tube. 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. 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 3 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 224.

[0120] Synthesis of compound 266 in Example 9:

[0121]

[0122] Under nitrogen protection, 10 mmol of intermediate a-1, 10 mmol of raw material B-9, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6 and 70 mL of dichlorobenzene were added to a three-necked flask, and the mixture was refluxed for 20 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-9. LC-MS: Measured value: 434.11 ([M+H] + ), theoretical value: 433.16.

[0123] Under nitrogen protection, 10 mmol of intermediate a-9, 10 mmol of raw material C-1, 20 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4, 50 mL of tetrahydrofuran and 5 mL of water were added to a three-necked flask, and the mixture was refluxed for 8 hours. After the reaction, the organic phase was separated by liquid separation, 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: 677.35 ([M+H] + ), theoretical value: 676.38.

[0124] Under nitrogen protection, 10 mmol of intermediate b-9 and 5 ml of o-dichlorobenzene were added into a pressure-resistant sealed tube. 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 2.5 hours. Then, 15 mmol of boron tribromide was added at 0 °C, and the mixture was transferred to room temperature and reacted for another 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 2 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain Compound 266.

[0125] Synthesis of Compound 274 in Example 10:

[0126]

[0127] Under nitrogen protection, 10 mmol of raw material A-10, 10 mmol of NBS, and 30 ml of glacial acetic acid were added to a three-necked flask and reacted at 0 °C for 5 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-10. LC-MS: Measured value: 280.03 ([M+H] + )), theoretical value: 279.06. 1 1H NMR (500 MHz, chloroform-d) δ 7.6 (dd, 1H), 7.4 (dd, 1H), 6.9 (t, 1H), 6.2 (s, 1H), 1.9–1.5 (m, 8H), 1.3 (s, 3H), 1.1 (s, 3H).

[0128] Under nitrogen protection, 10 mmol of intermediate a-10, 10 mmol of bis(pinacolato)diboron, 5 mmol of potassium acetate, 0.1 mmol of Pd(dppf)Cl2, and 30 ml of 1,4-dioxane were added to a three-necked flask and refluxed for 14 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-10. LC-MS: Measured value: 328.29 ([M+H] + )), theoretical value: 327.24.

[0129] Under nitrogen protection, 10 mmol of intermediate a-1, 10 mmol of raw material B-10, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6, and 70 mL of dichlorobenzene were added to a three-necked flask and refluxed for 24 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-10. LC-MS: Measured value: 510.26 ([M+H] + )), theoretical value: 509.19.

[0130] In a three-necked flask, under nitrogen protection, 10 mmol of intermediate c-10, 10 mmol of intermediate b-10, 10 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4 and 200 ml of toluene were added and refluxed for 18 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate d-10. LC-MS: Measured value: 675.30 ([M+H] + ), theoretical value: 674.37.

[0131] Under nitrogen protection, 10 mmol of intermediate d-10 and 5 ml of o-dichlorobenzene were added to a pressure-resistant sealed tube. 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 1.5 hours. 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 mixture was heated to 200 °C and reacted for 3 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 274.

[0132] Synthesis of Compound 296 in Example 11:

[0133]

[0134] Under nitrogen protection, 10 mmol of intermediate a-1, 10 mmol of raw material B-11, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6 and 70 mL of dichlorobenzene were added to a three-necked flask and refluxed for 72 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-11. LC-MS: Measured value: 464.26 ([M+H] + ), theoretical value: 463.21.

[0135] In a three-necked flask, under nitrogen protection, 10 mmol of intermediate a-11, 10 mmol of intermediate b-10, 10 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4 and 200 ml of toluene were added and refluxed for 14 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-11. LC-MS: Measured value: 629.34 ([M+H] + ), theoretical value: 628.38.

[0136] Under nitrogen protection, 10 mmol of intermediate b-11 and 5 ml of o-dichlorobenzene were added to a pressure-resistant sealed tube. 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 2.5 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 296.

[0137] Example 12 Synthesis of Compound 330:

[0138]

[0139] Under nitrogen protection, 10 mmol of intermediate a-1, 10 mmol of raw material B-12, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6 and 70 mL of dichlorobenzene were added to a three-necked flask, and the mixture was refluxed for 16 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-12. LC-MS: Measured value: 458.25 ([M+H] + ), theoretical value: 457.16.

[0140] In a three-necked flask, under nitrogen protection, 10 mmol of intermediate a-12, 10 mmol of raw material A-2, 10 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4 and 200 ml of toluene were added, and the mixture was 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 b-12. LC-MS: Measured value: 703.44 ([M+H] + ), theoretical value: 702.40.

[0141] Under nitrogen protection, 10 mmol of intermediate b-12 and 5 ml of o-dichlorobenzene were added to a pressure-resistant sealed tube. 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 4 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 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 330.

[0142] Example 13 Synthesis of Compound 346:

[0143]

[0144] Under nitrogen protection, 10 mmol of intermediate a-1, 10 mmol of raw material B-13, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6 and 70 mL of dichlorobenzene were added to a three-necked flask, and the mixture was refluxed for 38 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-13. LC-MS: Measured value: 384.13 ([M+H] + ), theoretical value: 383.14.

[0145] In a three-necked flask, under nitrogen protection, 10 mmol of intermediate a-13, 10 mmol of raw material C-1, 10 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4 and 200 ml of toluene were added, and the mixture was refluxed for 14 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-13. LC-MS: Measured value: 627.39 ([M+H] + ), theoretical value: 626.37.

[0146] Under nitrogen protection, 10 mmol of intermediate b-13 and 5 ml of o-dichlorobenzene were added to a pressure-resistant sealed tube. A n-hexane solution of 12 mmol of n-butyllithium 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, 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 3 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 346.

[0147] Example 14 Synthesis of Compound 370:

[0148]

[0149] Under nitrogen protection, 10 mmol of intermediate a-1, 10 mmol of raw material B-14, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6 and 70 mL of dichlorobenzene were added to a three-necked flask, and the mixture was refluxed for 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-14. LC-MS: Measured value: 360.11 ([M+H] + ), theoretical value: 359.14.

[0150] In a three-necked flask, under nitrogen protection, 10 mmol of intermediate a-14, 10 mmol of raw material C-1, 10 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4 and 200 ml of toluene were added and refluxed for 24 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-14. LC-MS: Measured value: 603.43([M+H] + ) and the theoretical value: 602.37.

[0151] Under nitrogen protection, 10 mmol of intermediate b-14 and 5 ml of o-dichlorobenzene were added to a pressure-resistant sealed tube. 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 3 hours. Then, 20 mmol of N,N-diisopropylethylamine was added to the system at 0 °C and heated to 200 °C and reacted for 2 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 370.

[0152] The structural characterizations of the compounds obtained in each example are shown in Table 1

[0153] Table 1

[0154]

[0155]

[0156] The compounds of the present invention can be used in light-emitting devices and can be used as doping materials for the light-emitting layer. The physical and chemical properties of the compounds prepared in the above examples of the present invention were tested, and the test results are shown in Table 2:

[0157] Table 2

[0158] Compound PLQY (%) FWHM (nm) 8 89 25 30 90 29 74 93 33 96 91 23 118 91 34 140 94 24 161 94 21 224 92 37 266 89 32 274 90 24 296 86 31 330 90 28 346 93 30 370 89 22

[0159] Note: PLQY (fluorescence quantum yield) and FWHM (full width at half maximum) were measured by a Horiba Fluorolog-3 series fluorescence spectrometer in the thin film state.

[0160] From the data in the above table, it can be seen that the compounds of the present invention have a high fluorescence quantum efficiency as doping materials, and the fluorescence quantum efficiency of the materials is close to 100%; at the same time, the spectral FWHM of the materials is narrow, which can effectively improve the color gamut of the device and the light-emitting efficiency of the device; finally, the evaporation decomposition temperature of the materials is high, which can inhibit the evaporation decomposition of the materials and effectively improve the device life.

[0161] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 1-14 and Device Comparative Examples 1-3. The manufacturing processes of Device Examples 2-14 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 Table 3-1 and Table 4 respectively

[0162] Device Example 1

[0163] As Figure 1 shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed with a cleaning agent (Semiclean M-L20), pure water, and then dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as the host materials, and Compound 8 is used as the doping material. The mass ratio of GH-1, GH-2, and Compound 8 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, 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, and the film thickness is 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, 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. This layer is used as the cathode layer 10

[0164] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 15-28 and Device Comparative Examples 4-6. The manufacturing processes of Device Examples 16-28 and Device Comparative Examples 4-6 of the present invention are exactly the same as those of Device Example 15, 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 Table 3-2 and Table 4 respectively.

[0165] Device Example 15

[0166] 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. GH-1 and GH-2 are used as the host materials, GD-1 is used as the first doping material, and compound 8 is used as the second doping material. The mass ratio of GH-1, GH-2, GD-1, and compound 8 is 66:30:3:1, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously evaporated by vacuum evaporation, with a film thickness of 5 nm, 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.

[0167] The molecular structural formulas of the related materials are as follows:

[0168]

[0169] 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 operating voltage, current efficiency, and device lifetime of the device are measured. The device examples 15 - 28 and comparative examples 4 - 6 prepared by the same method are shown in Table 3 - 2; the test results of the voltage, current efficiency, and lifetime of the obtained devices are shown in Table 4.

[0170] Table 3 - 1

[0171]

[0172]

[0173] Table 3 - 2

[0174]

[0175] Table 4

[0176]

[0177] Note: The voltage, current efficiency, and emission peak are measured using an IVL (current-voltage-luminance) test system (Suzhou FushiDa Scientific Instrument Co., Ltd.); the lifetime test system is the EAS-62C type OLED device lifetime tester from System Technology Research Co., Ltd. of Japan; LT95 refers to the time when the device luminance decays to 95%; all data are measured at 10 mA / cm 2 below.

[0178] From the device data results in Table 4, it can be seen that the emission peaks of Comparative Examples 1-6 of the device are in the blue light region, while the emission peaks of Examples 1-28 of the device are in the green light region. Compared with Comparative Examples 1-3 of the device, the current efficiency and device lifetime in Examples 1-14 of the device are both higher than those in the comparative examples; compared with Comparative Examples 4-6 of the device, the current efficiency and device lifetime of Examples 15-28 of the device have been greatly improved compared to the OLED devices with known materials.

[0179] 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 principle of the present invention shall be included within the protection scope of the present invention.

Claims

1. A boron-containing organic compound, characterized in that, The structure of the organic compound is shown as any one of general formulas (A-1) to (A-12): In general formulas (A-1) to (A-12), Z represents C-R1; Each occurrence of R1, which is the same or different, represents a hydrogen atom, a deuterium 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 phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; R2 is represented as a substituted or unsubstituted C6-C 30 aryl, a substituted or unsubstituted C2-C 30 heteroaryl; X represents O, S, N(R3); R3 is represented as a substituted or unsubstituted C6-C 30 aryl, a substituted or unsubstituted C2-C 30 heteroaryl; R a 、R b 、R c each independently represents a hydrogen atom, a deuterium 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 phenyl-substituted amino group, a tert-butylbenzene-substituted amino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; The substituents for the substituent groups are each independently selected from one or more of a deuterium atom, a halogen atom, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 2 to 30 carbon atoms.

2. The boron-containing organic compound according to claim 1, wherein Each occurrence of R1, which may be the same or different, 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 group, an xanthone group, a phenyl-substituted triazine group, a methoxy group, a tert-butoxy group; R2 represents 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 tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl group, an xanthone group, a phenyl-substituted triazine group.

3. The boron-containing organic compound according to claim 1, wherein R3 is represented by one of phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, naphthyl, anthryl, 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, tert-butyl-substituted dibenzofuryl, xanthenone, phenyl-substituted triazinyl.

4. The boron-containing organic compound according to claim 1, wherein The R a , R b , R c are each independently represented by 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 group, an xanthone group, a phenyl-substituted triazine group, a methoxy group, a tert-butoxy group.

5. The boron-containing organic compound according to claim 1, wherein The specific structure of the organic compound is any one of the following structures:

6. An organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, the organic light-emitting functional layer including a light-emitting layer, characterized in that, The light-emitting layer contains the boron-containing organic compound according to any one of claims 1-5.

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

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

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

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