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

Abstract

The present invention discloses a boron-containing organic compound and an organic electroluminescent device prepared therefrom, belonging to the field of semiconductor technology. The structure of the organic compound of the present invention is shown in the general formula (1). 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 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 and an organic light-emitting device prepared therefrom. Background Art

[0002] Limited by early technology, traditional fluorescent doping materials can only utilize 25% of the singlet excitons formed by electrical excitation for luminescence, resulting in a relatively low internal quantum efficiency of the device (up to 25%), and the external quantum efficiency is generally lower than 5%, showing a large gap compared with the efficiency of phosphorescent devices. Due to the strong spin-orbit coupling of heavy atom centers in phosphorescent materials, which enhances intersystem crossing, they can effectively utilize both singlet and triplet excitons formed by electrical excitation for luminescence, enabling the internal quantum efficiency of the device to reach 100%. However, most phosphorescent materials are expensive, with poor material stability, poor color purity, and serious efficiency roll-off of the device, which limits 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 yield and narrow full width at half maximum through molecular engineering. Breakthroughs have been achieved in blue fluorescent doping materials, and the full width at half maximum of boron-based materials can be reduced to less than 30 nm. In the green light region, to which the human eye is more sensitive, the research mainly focuses on phosphorescent doping materials, but it is difficult to narrow their emission peak shape through simple methods. Therefore, to meet higher color rendering standards, it is of great significance to study highly efficient green fluorescent doping materials with narrow full width at half maximum.

[0004] In addition, the TADF sensitized fluorescence technology (TSF) combines TADF materials with fluorescent doping materials. Using TADF materials as exciton sensitization media, the 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, 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 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 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 for meeting the BT.2020 display standards. Summary of the Invention

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

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

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

[0009]

[0010] M1 represents one of a substituted or unsubstituted C 6-30 aryl, a substituted or unsubstituted C 3-30 heteroaryl, or a substituted or unsubstituted C 6-30 cycloalkyl;

[0011] Z represents C(R1); each occurrence of R1, which may be the same or different, represents H, a deuterium atom, tritium, a halogen atom, a cyano group, a C 1-10 alkyl or silyl group, a substituted amino group, a substituted or unsubstituted C 6-30 aryl, or a substituted or unsubstituted C 3-30 heteroaryl; adjacent R1s may also form a C 6-30 aryl or a C 6-30 heteroaryl;

[0012] X represents one of N(R3) or C(R4)(R5); R2 and R3 each independently represent a C 1-10 alkyl or silyl group, a substituted or unsubstituted C 6-30 aryl, or a substituted or unsubstituted C3-30 One of heteroaryl groups; X may also form a C with adjacent M1 6-30 aryl group or C 6-30 heteroaryl group;

[0013] R4 and R5 represent H, deuterium atom, tritium, halogen atom, cyano group, C 1-10 alkyl group or silyl group, substituted amino group, substituted or unsubstituted C 6-30 aryl group, substituted or unsubstituted C 3-30 heteroaryl group;

[0014] The substituents for the substituting groups are each independently selected from deuterium atom, tritium atom, halogen atom, C1-C 10 alkyl group, C3-C 10 cycloalkyl group, C6-C 30 aryl group, C2-C 30 heteroaryl group, or one or more of them.

[0015] In a preferred embodiment, the structure of the organic compound is represented by General Formula (2) or General Formula (3):

[0016]

[0017] In General Formula (2) and General Formula (3), the meanings of Z, M1, R2, and R3 are the same as defined above; R3 may also form a C with adjacent M1 6-30 aryl group or C 6-30 heteroaryl group; R2 may also form a fused ring structure with adjacent R1.

[0018] In a preferred embodiment, the structure of the organic compound is represented by any one of General Formulas (4) to (22):

[0019]

[0020] In General Formulas (4) to (22), the meanings of Z and R2 are the same as defined above;

[0021] Y represents O, S, C(R4)(R5) or Si(R6)(R7); R4, R5, R6, and R7 each independently represent substituted or unsubstituted C1-C 10 alkyl group, substituted or unsubstituted C3-C 10 cycloalkyl group, substituted or unsubstituted C1-C 10 alkoxy group, substituted or unsubstituted C6-C 10 aryloxy group, substituted or unsubstituted arylamino group, substituted or unsubstituted C6-C 30 aryl group, substituted or unsubstituted C2-C 30 heteroaryl group.

[0022] In a preferred embodiment, the structure of the organic compound is represented by any one of general formulas (1-1) to (1-7):

[0023]

[0024] In general formulas (1-1) to (1-7), Z represents C(R1); each occurrence of R1, which may be the same or different, represents H, a deuterium atom, tritium, a halogen atom, a cyano group, an alkyl or silyl group of C 1-10 , a substituted amino group, a substituted or unsubstituted C 6-30 aryl group, a substituted or unsubstituted C 3-30 heteroaryl group; adjacent R1s may also form a C 6-30 aryl group or a C 6-30 heteroaryl group;

[0025] R a 、R b 、R c 、R d 、R e each occurrence, which may be the same or different, represents H, a deuterium atom, tritium, a halogen atom, a cyano group, an alkyl or silyl group of C 1-10 , a C 6-30 aryl group or a C 2-30 heteroaryl group-substituted amino group, a substituted or unsubstituted C 6-30 aryl group, a substituted or unsubstituted C 3-30 heteroaryl group;

[0026] X1 represents O, S, N(R8), C(R9)(R 10 ), or Si(R 11 )(R 12 ); R8, R9, R 10 、R 11 、R 12 each independently represents a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group;

[0027] The substituents for the substituent groups 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 30One or more of heteroaryl groups.

[0028] 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, an xanthone group, a phenyl-substituted triazinyl group, a phenyl-substituted boranyl group, a methoxy group, or a tert-butoxy group.

[0029] Preferred embodiment, each occurrence of R2 and R3, which are the same or different, represents one of adamantyl, 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 boranyl;

[0030] Preferred embodiment, R4, R5, R6 and R7 each independently represent one of 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, 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.

[0031] Preferred embodiment, the R a 、R b 、R c 、Rd , R e Each occurrence, which can be the same or different, represents one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, an adamantyl group, a methyl group, a deuterated methyl group, a tritiated methyl group, a trifluoromethyl group, an ethyl group, a deuterated ethyl group, a tritiated ethyl group, an isopropyl group, a deuterated isopropyl group, a tritiated isopropyl group, a tert-butyl group, a deuterated tert-butyl group, a tritiated tert-butyl group, a cyclopentyl group, a deuterated cyclopentyl group, a tritiated cyclopentyl group, a methyl-substituted cyclopentyl group, a cyclohexyl group, a phenyl group, a deuterated phenyl group, a tritiated phenyl group, a biphenyl group, a deuterated biphenyl group, a tritiated biphenyl group, a terphenyl group, a deuterated terphenyl group, a tritiated terphenyl group, a diphenyl ether group, a methyl-substituted diphenyl ether group, a naphthyl group, an anthracenyl group, a phenanthryl group, a 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;

[0032] The R8, R9, R 10 , R 11 , R 12Independently represented as 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, naphthyl, anthracenyl, 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, phenyl-substituted amino, tert-butylbenzene-substituted amino, tert-butyl-substituted dibenzofuranyl, phenyl-substituted tert-butyl, xanthenone, phenyl-substituted triazinyl, or one of them.

[0033] In a preferred embodiment, the specific structure of the organic compound is any one of the following structures:

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047] 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.

[0048] In a preferred embodiment, the light-emitting layer contains a host material and a doping material, and the doping material contains the boron-containing organic compound.

[0049] In a preferred embodiment, the light-emitting layer contains a first host material, a second host material and a doping material. At least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing organic compound described above.

[0050] In a preferred embodiment, the light-emitting layer contains a host material, an exciton sensitizing material and a doping material. The exciton sensitizing material is a metal element-containing complex, and the doping material is the boron-containing organic compound described above.

[0051] The beneficial technical effects of the present invention are as follows:

[0052] (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;

[0053] (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%;

[0054] (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;

[0055] (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; Description of the Drawings

[0056] Figure 1 It is a schematic structural diagram of the materials listed in the present invention applied to an OLED device;

[0057] 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

[0058] The present invention will be further described below with reference to the drawings and specific embodiments, but it is not limited to the present invention.

[0059] The following examples are intended to better explain the present invention, but the scope of the present invention is not limited thereto.

[0060] 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;

[0061] Synthesis of Compound 20 in Example 1:

[0062]

[0063] Under nitrogen protection, 5 mmol of raw material A-1, 10 mmol of raw material B-1, 10 mmol of potassium carbonate and 50 mL of dichloromethane were added to a three-necked flask and reacted at room temperature 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 intermediate a-1. LC-MS: Measured value: 472.13 ([M+H] + ), Theoretical value: 471.20.

[0064] Under nitrogen protection, 10 mmol of raw material C-1, 10 mmol of intermediate a-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 21 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-1. LC-MS: Measured value: 543.30 ([M+H] + ), Theoretical value: 542.29.

[0065] Under nitrogen protection, 10 mmol of intermediate b-1, 10 mmol of raw material D-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 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 c-1. LC-MS: Measured value: 786.55 ([M+H] + ), Theoretical value: 785.51.

[0066] Under nitrogen protection, 10 mmol of intermediate c-1, 10 mmol of tetrabutylammonium fluoride and 50 mL of tetrahydrofuran were added to a three-necked flask and reacted at room temperature for 5 hours. After the reaction was completed, the organic layer was concentrated and then purified by silica gel column chromatography to obtain intermediate d-1. LC-MS: Measured value: 672.41 ([M+H] + ), Theoretical value: 671.42.

[0067] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate d-1 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 4 hours. Subsequently, 20 mmol of N,N-diisopropylethylamine was added to the reaction system at 0 °C, and the reaction was heated to 200 °C and reacted for 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 20. 1 H NMR (400 MHz, chloroform-d) δ 8.16 - 8.11 (m, 1H), 8.09 - 8.00 (m, 2H), 7.92 (t, 2H), 7.87 (d, 1H), 7.70 - 7.68 (m, 1H), 7.66 (d, 1H), 7.45 (d, 1H), 7.27 (dd, 1H), 7.22 - 7.14 (m, 4H), 1.48 (s, 9H), 1.39 (s, 9H), 1.25 (d, 18H).

[0068] Synthesis of compound 33 in Example 2:

[0069]

[0070] Under nitrogen protection, 10 mmol of raw material A-2, 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 intermediate a-2 was obtained by column chromatography separation. LC-MS: Measured value: 208.13 ([M + H] + )), theoretical value: 207.08. 1 H NMR (500 MHz, chloroform-d) 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).

[0071] Under nitrogen protection, 10 mmol of intermediate a-2, 10 mmol of intermediate a-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 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-2. LC-MS: Measured value: 599.40 ([M + H] + )), theoretical value: 598.35.

[0072] Under nitrogen protection, 10 mmol of intermediate b-2, 10 mmol of raw material C-1, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6 and 70 mL of dichlorobenzene were added to a three-necked flask, and the mixture was refluxed for 40 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: 842.60 ([M+H] + ), theoretical value: 841.57.

[0073] Under nitrogen protection, 10 mmol of intermediate c-2, 10 mmol of tetrabutylammonium fluoride and 50 mL of tetrahydrofuran were added to a three-necked flask, and the reaction was carried out at room temperature for 5 hours. After the reaction was completed, the organic layer was concentrated and then purified by silica gel column chromatography to obtain intermediate d-2. LC-MS: Measured value: 728.51 ([M+H] + ), theoretical value: 727.49.

[0074] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate d-2 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 3 hours. Then, 20 mmol of N,N-diisopropylethylamine was added to the system at 0 °C, and the temperature was heated to 200 °C and reacted for 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 33. 1 H NMR (400 MHz, chloroform-d) δ 8.39 - 8.34 (m, 2H), 8.14 (d, 1H), 8.02 - 7.98 (m, 2H), 7.94 (d, 1H), 7.88 (d, 1H), 7.73 - 7.68 (m, 2H), 7.46 - 7.41 (m, 2H), 7.39 (dd, 1H), 7.35 (dd, 1H), 1.56 (s, 9H), 1.42 - 1.35 (m, 18H), 1.33 - 1.24 (m, 18H).

[0075] Synthesis of Compound 137 in Example 3:

[0076]

[0077] 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 21 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: 338.22 ([M+H] + ), theoretical value: 337.19.

[0078] Under nitrogen protection, 10 mmol of intermediate a-3, 10 mmol of intermediate b-2, 0.5 mmol of Pd2(dba)3, 10 mmol of potassium carbonate and 40 ml of anhydrous toluene were added to a three-necked flask, and the mixture was refluxed for 26 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: 844.48 ([M+H] + ), theoretical value: 843.50.

[0079] Under nitrogen protection, 10 mmol of intermediate b-3, 10 mmol of tetrabutylammonium fluoride and 50 mL of tetrahydrofuran were added to a three-necked flask, and the reaction was carried out at room temperature for 2 hours. After the reaction was completed, the organic layer was concentrated and then purified by silica gel column chromatography to obtain intermediate c-3. LC-MS: Measured value: 786.50 ([M+H] + ), theoretical value: 785.47.

[0080] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate c-3 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 3 hours. Then, 15 mmol of boron tribromide was added at 0 °C, and the reaction was continued at room temperature for 3.5 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 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 137. 1 1H NMR (400 MHz, chloroform-d) δ 8.13 - 8.09 (m, 1H), 7.88 (d, 1H), 7.84 (dd, 2H), 7.68 (dd, 2H), 7.59 (d, 1H), 7.51 (dd, 1H), 7.33 (dd, 1H), 7.26 - 7.19 (m, 4H), 7.18 - 7.13 (m, 2H), 1.44 - 1.37 (m, 36H), 1.28 (s, 9H).

[0081] Synthesis of Compound 155 in Example 4:

[0082]

[0083] Under nitrogen protection, 10 mmol of intermediate b-2, 10 mmol of raw material A-4, 20 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4, 100 mL of tetrahydrofuran 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 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 a-4. LC-MS: Measured value: 691.49 ([M+H] + ), theoretical value: 690.44.

[0084] Under nitrogen protection, 10 mmol of intermediate a-4, 10 mmol of tetrabutylammonium fluoride and 50 mL of tetrahydrofuran were added to a three-necked flask, and the reaction was carried out at room temperature for 4 hours. After the reaction was completed, the organic layer was concentrated, and then purified by silica gel column chromatography to obtain intermediate b-4. LC-MS: Measured value: 577.33 ([M+H] + ), theoretical value: 576.35.

[0085] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-4 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 4 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 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 155. 1 H NMR (400 MHz, chloroform-d) δ8.26 (d, 1H), 8.22 (d, 1H), 7.96 - 7.89 (m, 3H), 7.78 - 7.69 (m, 2H), 7.45 (d, 1H), 7.39 (d, 1H), 7.34 (dd, 1H), 7.25 - 7.18 (m, 4H), 1.40 - 1.35 (m, 18H), 1.26 (s, 9H).

[0086] Synthesis of Compound 179 in Example 5:

[0087]

[0088] Under nitrogen protection, 10 mmol of intermediate b-2, 10 mmol of raw material A-5, 20 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4, 100 mL of tetrahydrofuran and 5 mL of water were added to a three-necked flask, and the mixture was refluxed for 15 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 a-5. LC-MS: Measured value: 741.49([M+H] + ), theoretical value: 740.45.

[0089] Under nitrogen protection, 10 mmol of intermediate a-5, 10 mmol of tetrabutylammonium fluoride and 50 mL of tetrahydrofuran were added to a three-necked flask, and the reaction was carried out at room temperature for 4 hours. After the reaction was completed, the organic layer was concentrated, and then purified by silica gel column chromatography to obtain intermediate b-5. LC-MS: Measured value: 627.39([M+H] + ), theoretical value: 626.37.

[0090] 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, the system was heated to 60 °C and reacted for 8 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 temperature was 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 179. 1 1H NMR (400 MHz, chloroform-d) δ 8.86 - 8.79 (m, 1H), 8.68 - 8.55 (m, 1H), 8.46 (d, 1H), 8.41 (dd, 1H), 8.24 (d, 1H), 8.14 (dt, 1H), 7.92 - 7.88 (m, 1H), 7.78 (d, 1H), 7.54 - 7.50 (m, 2H), 7.44 (d, 1H), 7.35 - 7.32 (td, 1H), 7.29 - 7.27 (t, 1H), 7.26 - 7.18 (m, 3H), 1.42 - 1.36 (m, 18H), 1.32 (s, 9H).

[0091] Synthesis of compound 203 in Example 6:

[0092]

[0093] Under nitrogen protection, 10 mmol of intermediate b-2, 10 mmol of raw material A-6, 20 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4, 100 mL of tetrahydrofuran and 5 mL of water were added to a three-necked flask, and the mixture was refluxed for 14 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 a-6. LC-MS: Measured value: 791.51 ([M+H] + ), theoretical value: 790.47.

[0094] Under nitrogen protection, 10 mmol of intermediate a-6, 10 mmol of tetrabutylammonium fluoride and 50 mL of tetrahydrofuran were added to a three-necked flask, and the reaction was carried out at room temperature for 4 hours. After the reaction was completed, the organic layer was concentrated, and then purified by silica gel column chromatography to obtain intermediate b-6. LC-MS: Measured value: 677.43 ([M+H] + ), theoretical value: 676.38.

[0095] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-6 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 5 hours. Then, 15 mmol of boron tribromide was added at 0 °C, and the reaction was continued at room temperature for 4.5 hours. Then, 20 mmol of N,N-diisopropylethylamine was added to the system at 0 °C, and the temperature was 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 203. 1 1H NMR (400 MHz, chloroform-d) δ 8.76 - 8.68 (m, 1H), 8.62 - 8.55 (m, 2H), 8.49 (d, 1H), 8.25 (dd, 1H), 8.13 (d, 1H), 7.98 - 7.89 (m, 2H), 7.82 (dd, 1H), 7.77 (d, 1H), 7.55 - 7.52 (m, 2H), 7.48 (td, 2H), 7.36 (t, 1H), 7.34 - 7.22 (m, 3H), 1.38 - 1.32 (m, 18H), 1.27 (s, 9H).

[0096] Synthesis of Compound 227 in Example 7:

[0097]

[0098] Under nitrogen protection, 10 mmol of intermediate b-2, 10 mmol of raw material A-7, 20 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4, 100 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 by liquid separation, 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: 867.53([M+H] + ), theoretical value: 866.50.

[0099] Under nitrogen protection, 10 mmol of intermediate a-7, 10 mmol of tetrabutylammonium fluoride and 50 mL of tetrahydrofuran were added to a three-necked flask, and the reaction was carried out at room temperature for 3 hours. After the reaction, the organic layer was concentrated, and then purified by silica gel column chromatography to obtain intermediate b-7. LC-MS: Measured value: 753.44([M+H] + ), theoretical value: 752.41.

[0100] In a sealed pressure-resistant 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 3 hours, then 15 mmol of boron tribromide was added at 0 °C, transferred to room temperature and continued to react for 2.5 hours, and 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, the organic layer was concentrated under reduced pressure, and then purified by silica gel column chromatography to obtain compound 227. 1 1H NMR(400MHz, chloroform-d) δ9.58(s,1H),8.68(s,1H),8.48(d,1H),8.42(dd,1H),8.22-8.17(m,1H),8.15(d,1H),7.99-7.92(m,1H),7.86-7.79(m,1H),7.77(d,1H),7.69-7.58(m,6H),7.48-7.38(m,4H),7.31(dt,3H),1.38-1.30(m,18H),1.25(s,9H).

[0101] Synthesis of Compound 251 in Example 8:

[0102]

[0103] Under nitrogen protection, 10 mmol of intermediate b-2, 10 mmol of raw material A-8, 20 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4, 100 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 separated by liquid separation, 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: 823.50 ([M+H] + ), theoretical value: 822.52.

[0104] Under nitrogen protection, 10 mmol of intermediate a-8, 10 mmol of tetrabutylammonium fluoride and 50 mL of tetrahydrofuran were added to a three-necked flask, and the reaction was carried out at room temperature for 3 hours. After the reaction was completed, the organic layer was concentrated, and then purified by silica gel column chromatography to obtain intermediate b-8. LC-MS: Measured value: 707.50 ([M+H] + ), theoretical value: 706.43.

[0105] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-8 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 4 hours. Then, 15 mmol of boron tribromide was added at 0 °C, and the reaction was continued at room temperature for 6 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 251. 1 H NMR(400MHz, chloroform-d) δ8.22(dd,2H),8.05(d,1H),7.98(d,1H),7.84-7.77(m,3H),7.65-7.57(m,2H),7.52-7.48(m,2H),7.44(d,1H),7.31-7.22(m,3H),1.37-1.33(m,18H),1.27-1.22(m,18H).

[0106] Synthesis of compound 275 in Example 9:

[0107]

[0108] Under nitrogen protection, 10 mmol of intermediate b-2, 10 mmol of raw material A-9, 20 mmol of potassium carbonate, 0.1 mmol of Pd(PPh3)4, 100 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 separated by liquid separation, 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: 773.45 ([M+H]+ ), theoretical value: 772.42.

[0109] Under nitrogen protection, 10 mmol of intermediate a-9, 10 mmol of tetrabutylammonium fluoride and 50 mL of tetrahydrofuran were added to a three-necked flask and reacted at room temperature for 3 hours. After the reaction, the organic layer was concentrated and then purified by silica gel column chromatography to obtain intermediate b-9. LC-MS: Measured value: 659.37 ([M+H] + ), theoretical value: 658.34.

[0110] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate b-9 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 6 hours. Then, 20 mmol of N,N-diisopropylethylamine was added to the system at 0 °C and heated to 200 °C and reacted for 16 hours. After the reaction, the pressure was reduced and the organic layer was concentrated, and then purified by silica gel column chromatography to obtain compound 275. 1 H NMR (400 MHz, chloroform-d) δ 8.53 (d, 1H), 8.22 (d, 1H), 8.13 - 8.05 (m, 1H), 7.92 (d, 1H), 7.78 (dd, 1H), 7.70 - 7.59 (m, 2H), 7.54 (d, 1H), 7.50 - 7.42 (m, 4H), 7.38 - 7.27 (m, 3H), 7.11 (t, 1H), 1.47 (d, 18H), 1.29 (s, 9H).

[0111] The structural characterizations of the compounds obtained in each example are shown in Table 1

[0112] Table 1

[0113]

[0114]

[0115] The compounds of the present invention can be used in light-emitting devices and can be used as a doping material 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:

[0116] Table 2

[0117]

[0118] Note: PLQY (photoluminescence quantum yield) and FWHM (full width at half maximum) were measured by a Horiba Fluorolog-3 series fluorescence spectrometer in the thin film state.

[0119] As can be seen from the data in the above table, 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%; at the same time, the spectral FWHM of the material is narrow, which can effectively improve the color gamut of the device and the luminous efficiency of the device.

[0120] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 1-9 and Device Comparative Examples 1-36. The manufacturing processes of the devices in Device Examples 2-9 and Device Comparative Examples 1-3 are exactly the same as those in 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 3-1 and 4 respectively.

[0121] Device Example 1

[0122] As Figure 1 shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness: 150 nm) is washed, that is, washed with a cleaning agent (Semiclean M-L20), washed with pure water, 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 host materials, and Compound 20 is used as a doping material. The mass ratio of GH-1, GH-2 and Compound 20 is 69:30:1, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously evaporated by vacuum evaporation, with a film thickness of 5 nm. This layer is the hole blocking layer 7. After the above hole blocking layer 7, ET-1 and Liq are continuously evaporated by vacuum evaporation, and the mass ratio of ET-1 and Liq is 1:1, with a film thickness of 30 nm. This layer is the electron transport layer 8. On the electron transport layer 8, a LiF layer with a film thickness of 1 nm is fabricated by a vacuum evaporation device. This layer is the electron injection layer 9. On the electron injection layer 9, a Mg:Ag electrode layer with a film thickness of 80 nm is fabricated by a vacuum evaporation device. The mass ratio of Mg and Ag is 1:9. This layer is used as the cathode layer 10.

[0123] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 10-18 and Device Comparative Examples 4-6. The manufacturing processes of Device Examples 11-18 and Device Comparative Examples 4-6 of the present invention are exactly the same as those of Device Example 10, and the same substrate materials and electrode materials are used. The film thicknesses of the electrode materials are also kept consistent. The difference is that the light-emitting layer materials in the devices are replaced. The layer structures and test results of each device example are shown in Tables 3-2 and 4 respectively.

[0124] Device Example 10

[0125] The transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (with a film thickness of 150 nm) is washed, that is, washed successively with a cleaning agent (Semiclean M-L20), pure water, and dried, and then washed with ultraviolet-ozone to remove organic residues on the surface of the transparent ITO. On the ITO anode layer 2 after the above washing, using a vacuum evaporation device, HT-1 and HI-1 with a film thickness of 10 nm are evaporated as the hole injection layer 3, and the mass ratio of HT-1 and HI-1 is 97:3. Then, HT-1 with a thickness of 60 nm is evaporated as the hole transport layer 4. Subsequently, EB-1 with a thickness of 30 nm is evaporated as the electron blocking layer 5. After the evaporation of the above electron blocking material is completed, the light-emitting layer 6 of the OLED light-emitting device is fabricated. GH-1 and GH-2 are used as host materials, GD-1 is used as the first doping material, and Compound 20 is used as the second doping material. The mass ratio of GH-1, GH-2, GD-1, and Compound 20 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. 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.

[0126] The molecular structural formulas of the related materials are shown as follows:

[0127]

[0128] 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 driving voltage, current efficiency, and lifetime of the device are measured. The test results of the driving voltage, current efficiency, and lifetime of the obtained device are shown in Table 4.

[0129] Table 3-1

[0130]

[0131]

[0132] Table 3-2

[0133]

[0134] Table 4

[0135]

[0136] Note: 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 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 are measured at 10 mA / cm 2 below.

[0137] It can be seen from the device data results in Table 4 that compared with Device Comparative Examples 1-3 and Comparative Examples 4-6, the compounds of the present invention have lower voltages in the devices, and both the current efficiency and device lifetime are higher compared with the comparative examples;

[0138] 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 (1-1) to (1-7): In General Formulas (1-1) to (1-7), Z represents C(R1); each occurrence of R1, which may be the same or different, represents H, a deuterium atom, a halogen atom, a cyano group, C 1-10 alkyl or silyl, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 3-30 heteroaryl, phenyl-substituted amino, tert-butylbenzene-substituted amino; R a 、R b 、R c 、R d 、R e Each occurrence of the same or different ones represents one of H, deuterium atom, halogen atom, cyano group, C 1-10 alkyl or silyl group, C 6-30 aryl or C 2-30 heteroaryl-substituted amino group, substituted or unsubstituted C 6-30 aryl, substituted or unsubstituted C 3-30 heteroaryl; X1 is represented as O, S, N(R8); R8 is represented as substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 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 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, characterized in that, 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 oxanthrone group, or a phenyl-substituted triazine group.

3. The boron-containing organic compound according to claim 1, wherein Said R a , R b , R c , R d , R e Each occurrence, the same or different, is one of 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 oxanthrone group, a phenyl-substituted triazinyl group; R8 represents 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 tert-butyl-substituted dibenzofuryl group, an oxanthrone group, or a phenyl-substituted triazine group.

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

5. An organic electroluminescent device, comprising a cathode and an anode, and an organic light-emitting functional layer therebetween, wherein the organic light-emitting functional layer includes a light-emitting layer, characterized in that, The light-emitting layer contains a host material and a doping material, and the doping material contains the boron-containing organic compound according to any one of claims 1-4.

6. The organic electroluminescent device according to claim 5, wherein the light-emitting layer comprises a first host material, a second host material, and a doping material, characterized in that At least one of the first host material and the second host material is a TADF material, and the doping material is the boron-containing organic compound according to any one of claims 1-4.

7. The organic light-emitting device according to claim 5, wherein the light-emitting layer comprises a host material, an exciton sensitizing material, and a doping material, characterized in that The exciton sensitizing material is a metal element-containing complex, and the doping material contains the boron-containing organic compound according to any one of claims 1-4.

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