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

Abstract

The present invention discloses a boron-containing resonant 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 general formula (1). The compound of the present invention has a narrow full width at half maximum and a high fluorescence quantum yield. 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 and efficiency of the device, reducing the operating voltage of the device and increasing the lifespan of the device.

Description

Technical Field

[0001] The present invention relates to the field of semiconductor technology, and particularly to a boron-containing resonant organic compound and an organic electroluminescent device prepared therefrom. Background Art

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

[0003] With the advent of the 5G era, higher requirements are put forward for the color rendering standard. In addition to being efficient and stable, the luminescent material also requires a narrower full width at half maximum to improve the color purity of device luminescence. Fluorescent doping materials can achieve high fluorescence quantum and narrow full width at half maximum through molecular engineering. Breakthroughs have been achieved in blue fluorescent doping materials, and the full width at half maximum of boron-based materials can be reduced to less than 30 nm. In the green light region, which is more sensitive to the human eye, 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 high-efficiency 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, which can also achieve a 100% internal quantum efficiency of the device. This technology can make up for the deficiency of 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 110492005A and CN 110492009A, 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 specifications. Summary of the Invention

[0006] In view of the above problems existing in the prior art, the present invention provides a boron-containing resonance 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 resonance organic compound, the structure of the organic compound is shown in general formula (1):

[0009]

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

[0011] Each occurrence of R1 is the same or different and represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; two adjacent R1s can also be connected to form a ring;

[0012] R2 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-C10 An 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; R2 may also be connected to the adjacent R1 to form a ring;

[0013] M1 and M2 represent a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group, a substituted or unsubstituted C3-C 10 cycloalkyl group;

[0014] The substituents for the substituting 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 30 heteroaryl group, or one or more of them.

[0015] Preferably, the structure of the organic compound is shown as any one of general formula (2) to general formula (6):

[0016]

[0017] In general formula (2) - general formula (6), the meanings of Z, M1, and M2 are the same as the definitions in the above text;

[0018] X represents O, S, Se, N(R3), C(R4)(R5), or Si(R6)(R7);

[0019] R3 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;

[0020] R4, R5, R6, and R7 each independently represent a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C1-C 10 alkoxy group, a substituted or unsubstituted C6-C 10 aryloxy group, a substituted or unsubstituted arylamino group, a substituted or unsubstituted C6-C30 One of aryl, substituted or unsubstituted C2-C 30 heteroaryl;

[0021] The substituents for the substituted groups are each independently selected from a deuterium atom, a tritium atom, C1-C 10 alkyl, C3-C 10 cycloalkyl, C6-C 30 aryl, C2-C 30 one or more of heteroaryl.

[0022] Preferably, the structure of the organic compound is shown as any one of general formula (7) to general formula (26):

[0023]

[0024]

[0025] In general formula (7) to general formula (26), the meaning of Z is as defined above;

[0026] X each independently represents O, S, Se, N(R3), C(R4)(R5) or Si(R6)(R7);

[0027] R3 each independently represents substituted or unsubstituted C1-C 10 alkyl, substituted or unsubstituted C3-C 10 cycloalkyl, substituted or unsubstituted C1-C 10 alkoxy, substituted or unsubstituted C6-C 10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 one of heteroaryl;

[0028] R4, R5, R6, R7 each independently represent 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 C6-C 10 aryloxy, substituted or unsubstituted arylamino, substituted or unsubstituted C6-C 30 aryl, substituted or unsubstituted C2-C 30 one of heteroaryl;

[0029] 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-C30 One or more of aryl, C2-C 30 heteroaryl.

[0030] Preferably, the structure of the organic compound is represented by any one of general formulas (1-1) to (1-9):

[0031]

[0032] In general formulas (1-1) to (1-9), Z represents C-R1;

[0033] Each occurrence of R1 is the same or different and represents a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, a substituted or unsubstituted C1-C 10 alkyl, a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C1-C 10 alkoxy, a substituted or unsubstituted C6-C 10 aryloxy, a substituted or unsubstituted arylamino, a substituted or unsubstituted C6-C 30 aryl, a substituted or unsubstituted C2-C 30 heteroaryl; two adjacent R1s can also be connected to form a ring;

[0034] Each X independently represents O, S, Se, N(R3), C(R4)(R5) or Si(R6)(R7);

[0035] Each R3 independently represents a substituted or unsubstituted C1-C 10 alkyl, a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C6-C 30 aryl, a substituted or unsubstituted C2-C 30 heteroaryl;

[0036] Each of R4, R5, R6, and R7 independently represents a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted C1-C 10 alkyl, a substituted or unsubstituted C3-C 10 cycloalkyl, a substituted or unsubstituted C6-C 30 aryl, a substituted or unsubstituted C2-C 30 heteroaryl;

[0037] R a 、R b 、R c 、R d 、R e Each independently represents a hydrogen atom, a deuterium atom, a tritium atom, a substituted or unsubstituted C1-C 10 alkyl, a substituted or unsubstituted C3-C10 A cycloalkyl group, a substituted or unsubstituted C6-C 30 An aryl group, a substituted or unsubstituted C2-C 30 One of the heteroaryl groups;

[0038] The substituents for the substituting 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 30 one or more of the heteroaryl groups.

[0039] Preferably, 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 triazine group, a phenyl-substituted boranyl group, a methoxy group, a tert-butoxy group;

[0040] R2, R3, R4, R5, R6, and R7 are each independently one of methyl, 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, dibenzothiophenyl, 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 triazine;

[0041] R a , R b , R c , R d , R e is each independently one of a hydrogen atom, a deuterium atom, a tritium atom, a halogen atom, 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, methyl-substituted diphenyl ether, naphthyl, anthracenyl, phenanthryl, pyridyl, phenyl-substituted pyridyl, quinolinyl, furyl, thienyl, benzofuranyl, dibenzofuranyl, dibenzothiophenyl, 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 triazine, phenyl-substituted boranyl, methoxy, tert-butoxy;

[0042] The substituents for the substituent groups are each independently selected from 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 anthraquinonyl group, a phenyl-substituted triazinyl group, a phenyl-substituted boranyl group, a methoxy group, and a tert-butoxy group.

[0043] Preferably, the specific structure of the organic compound is any one of the following structures:

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] 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 resonance-type organic compound.

[0058] In a preferred embodiment, the light-emitting layer contains a host material and a doping material, and the doping material contains the boron-containing resonance-type organic compound.

[0059] 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 resonance-type organic compound.

[0060] In a preferred embodiment, the light-emitting layer contains a host material, an exciton sensitizing material and a doping material, and the exciton sensitizing material is a metal-containing complex.

[0061] The beneficial technical effects of the present invention are as follows:

[0062] (1) When the compound of the present invention is applied to an OLED device, it can be used as a doping material for the light-emitting layer material, and can emit green fluorescence under the action of an electric field, and can be applied to the fields of OLED lighting or OLED display;

[0063] (2) The compound of the present invention has a high fluorescence quantum efficiency as a doping material, and the fluorescence quantum efficiency of the material is close to 100%;

[0064] (3) When the compound of the present invention is used as a doping material and a TADF sensitizer is introduced as the second host, the device efficiency can be effectively improved;

[0065] (4) The spectral FWHM of the compound of the present invention is narrow, which can effectively improve the color gamut of the device and improve the light-emitting efficiency of the device. Description of the Drawings

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

[0067] Among them, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, and 10 is a cathode layer. Detailed Embodiments

[0068] The technical solutions in the embodiments of the present invention will be clearly and completely described below in conjunction with the accompanying drawings in the embodiments of the present invention. Without conflict, the embodiments in the present invention and the features in the embodiments may be combined with each other. The present invention will be further described below in conjunction with the accompanying drawings and specific embodiments, but it is not limited to the present invention.

[0069] The following embodiments are intended to better explain the present invention, but the scope of the present invention is not limited thereto.

[0070] The raw materials involved in the synthesis examples of the present invention can all be obtained from the market or prepared by conventional preparation methods in the art;

[0071] Synthesis of Compound 2 in Example 1:

[0072]

[0073] Under nitrogen protection, 10 mmol of raw material A-1, 10 mmol of NaH, and 10 mL of anhydrous DMF were added to a three-necked flask, stirred at room temperature for 0.5 hour, then 10 mmol of raw material B-1 was added, and the reaction was carried out at room temperature for 5 hours. After the reaction was completed, 50 ml of deionized water was added, the white precipitate was filtered, the precipitate was dissolved in dichloromethane, dried over anhydrous sodium sulfate, filtered, and concentrated. The intermediate a-1 was obtained by column chromatography. LC-MS: Measured value: 372.07 ([M+H] + )), theoretical value: 371.03.

[0074] Under nitrogen protection, 10 mmol of intermediate a-1, 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 reaction was refluxed for 18 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: 443.21 ([M+H] + )), theoretical value: 442.12.

[0075] Under nitrogen protection, 10 mmol of raw material D-1, 10 mmol of intermediate b-1, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown-6, and 70 mL of dichlorobenzene were added to a three-necked flask, and the reaction was refluxed for 32 hours. After the reaction was completed, the organic layer was depressurized and concentrated, and then purified by silica gel column chromatography to obtain intermediate c-1. LC-MS: Measured value: 686.44 ([M+H] + )), theoretical value: 685.35.

[0076] Under oxygen - passing conditions, 10 mmol of intermediate c - 1 and 11 mmol of DMSO were dissolved in 30 ml of ethyl acetate. After heating to 60 °C, 12 mmol of HBr (48% concentration) was added and the reaction was carried out for 5 hours. The reaction system was cooled to room temperature, the solvent was removed by distillation under reduced pressure, and the concentrated reaction solution was separated and purified by column chromatography to obtain intermediate d - 1. LC - MS: Measured value: 764.25([M + H] + ), theoretical value: 763.26. 1 H NMR(400 MHz, deuterated chloroform) δ8.10 - 8.03(m, 1H), 8.00 - 7.95(m, 2H), 7.82(d, 2H), 7.77(s, 1H), 7.63 - 7.45(m, 10H), 7.36 - 7.29(m, 7H), 7.26(td, 1H), 1.33(s, 18H).

[0077] 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, the reaction system was heated to 60 °C and reacted for 2 hours. Then, 15 mmol of boron tribromide was added at 0 °C, and the reaction was continued at room temperature for 10 hours. Then, 20 mmol of N,N - diisopropylethylamine was added to the system at 0 °C, and the reaction was heated to 200 °C and reacted for 10 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 2.

[0078] 1 H NMR(400 MHz, deuterated chloroform) δ8.26(dd, 1H), 8.21(d, 1H), 8.12(dd, 1H), 7.88 - 7.82(m, 1H), 7.74(dd, 1H), 7.69(d, 1H), 7.65(dd, 2H), 7.62 - 7.55(m, 2H), 7.52 - 7.47(m, 2H), 7.43 - 7.35(m, 2H), 7.27 - 7.16(m, 8H), 1.33(s, 9H), 1.27(s, 9H).

[0079] Synthesis of compound 8 in Example 2:

[0080]

[0081] Under nitrogen protection, 10 mmol of raw material C-1, 10 mmol of raw material B-2, 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 14 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-2. LC-MS: Measured value: 278.13([M+H] + ), theoretical value: 277.07.

[0082] Under nitrogen protection, 10 mmol of intermediate a-2, 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 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 b-2. LC-MS: Measured value: 521.34([M+H] + ), theoretical value: 520.29.

[0083] Under oxygen conditions, 10 mmol of intermediate b-2 and 11 mmol of DMSO were dissolved in 30 ml of ethyl acetate. After heating to 60 °C, 12 mmol of HBr (48% concentration) was added and the reaction was carried out for 8 hours. The reaction system was cooled to room temperature, the solvent was removed by distillation under reduced pressure, and the concentrated reaction solution was separated and purified by column chromatography to obtain intermediate c-2. LC-MS: Measured value: 599.23([M+H] + ), theoretical value: 598.20. 1 H NMR (400 MHz, chloroform-d) δ 8.13 - 8.06 (m, 1H), 8.02 (d, 2H), 7.98 - 7.92 (m, 2H), 7.73 (dd, 1H), 7.52 - 7.48 (m, 6H), 7.23 - 7.15 (m, 5H), 1.39 (s, 18H).

[0084] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate c-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 13 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 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 8.

[0085] 1H NMR (400 MHz, deuterated chloroform) δ 8.26–8.19 (m, 2H), 8.01–7.85 (m, 1H), 7.83–7.77 (m, 2H), 7.70 (d, 1H), 7.68 (dd, 1H), 7.55–7.42 (m, 2H), 7.38–7.15 (m, 6H), 1.38 (s, 9H), 1.27 (s, 9H).

[0086] Example 3 Synthesis of Compound 59:

[0087]

[0088] Under nitrogen protection, 10 mmol of raw material A-3, 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, the reaction solution was concentrated and separated by column chromatography to obtain intermediate a-3. LC-MS: Measured value: 208.13 ([M+H] + ), theoretical value: 207.08. 1 H NMR (400 MHz, deuterated chloroform) δ 7.6 (d, 1H), 7.5 (d, 1H), 7.2 (d, 1H), 7.1 (dd, 1H), 5.1 (s, 1H), 1.5 (s, 9H).

[0089] Under nitrogen protection, 10 mmol of intermediate a-3, 10 mmol of raw material B-2, 15 mmol of potassium carbonate, 0.5 mmol of copper, 15 mmol of 18-crown ether-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 concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-3. LC-MS: Measured value: 334.17 ([M+H] + ), theoretical value: 333.13.

[0090] Under nitrogen protection, 10 mmol of raw material B-3, 10 mmol of raw material C-3, 15 mmol of potassium carbonate, 0.5 mmol of Pd2(dba)3, 1.5 mmol of tri-tert-butylphosphine and 50 mL of anhydrous toluene were added to a three-necked flask and refluxed for 10 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate c-3. LC-MS: Measured value: 322.25 ([M+H] + ), theoretical value: 321.21.

[0091] Under nitrogen protection, 10 mmol of intermediate c-3, 10 mmol of intermediate b-3, 15 mmol of potassium carbonate, 0.5 mmol of Pd2(dba)3, 1.5 mmol of 2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl and 50 mL of anhydrous o-xylene were added to a three-necked flask, and the mixture was refluxed for 36 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate d-3. LC-MS: Measured value: 619.38 ([M+H] + ), theoretical value: 618.36.

[0092] Under oxygen conditions, 10 mmol of intermediate d-3 and 11 mmol of DMSO were dissolved in 30 ml of ethyl acetate. After heating to 60 °C, 12 mmol of HBr (48% concentration) was added and the reaction was carried out for 12 hours. The reaction system was cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The concentrated reaction solution was separated and purified by column chromatography to obtain intermediate e-3. LC-MS: Measured value: 697.19 ([M+H] + ), theoretical value: 696.27. 1 H NMR (400 MHz, chloroform-d) δ 8.21 (d, 1H), 8.13 - 8.05 (m, 2H), 7.91 (s, 1H), 7.77 - 7.71 (m, 1H), 7.68 (dd, 1H), 7.51 - 7.49 (m, 4H), 7.22 - 7.14 (m, 4H), 7.09 - 7.02 (m, 2H), 6.81 - 6.75 (m, 2H), 1.54 - 1.36 (m, 27H).

[0093] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate e-3 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 18 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 8 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 59.

[0094] 1 H NMR (400 MHz, chloroform-d) δ 8.12 (d, 1H), 7.93 - 7.85 (m, 2H), 7.75 (d, 1H), 7.67 (d, 1H), 7.63 - 7.59 (m, 1H), 7.51 (dd, 2H), 7.27 - 7.18 (m, 6H), 7.09 - 7.02 (m, 2H), 1.36 - 1.27 (m, 27H).

[0095] Synthesis of Compound 63 in Example 4:

[0096]

[0097] Under nitrogen protection, 10 mmol of intermediate a-3, 10 mmol of raw material A-4, 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 was completed, 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: 434.11 ([M+H] + ), theoretical value: 433.16.

[0098] Under nitrogen protection, 10 mmol of intermediate a-4, 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 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 b-4. LC-MS: Measured value: 677.37 ([M+H] + ), theoretical value: 676.38.

[0099] Under oxygen condition, 10 mmol of intermediate b-4 and 11 mmol of DMSO were dissolved in 30 ml of ethyl acetate. After heating to 60 °C, 12 mmol of HBr (48% concentration) was added and the reaction was carried out for 8 hours. The reaction system was cooled to room temperature, the solvent was removed by distillation under reduced pressure, and the concentrated reaction solution was separated and purified by column chromatography to obtain intermediate c-4. LC-MS: Measured value: 755.27 ([M+H] + ), theoretical value: 754.29. 1 H NMR (400 MHz, chloroform-d) δ 8.39 - 8.36 (m, 2H), 8.23 (dd, 1H), 8.05 (dd, 1H), 7.93 - 7.81 (m, 4H), 7.72 (dd, 1H), 7.64 (s, 1H), 7.55 - 7.39 (m, 6H), 7.32 - 7.15 (m, 4H), 1.47 (s, 18H), 1.33 (s, 9H).

[0100] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate c-4 and 5 ml of o-dichlorobenzene were added. A solution of 12 mmol of n-butyllithium in n-hexane was added at 0 °C, the system was heated to 60 °C and reacted for 2 hours. Then, 15 mmol of boron tribromide was added at 0 °C, and the reaction was continued at room temperature for 18 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 16 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 63.

[0101] 1 H NMR (400 MHz, chloroform-d) δ 8.62–8.55 (m, 2H), 8.38–8.29 (m, 2H), 8.17 (dd, 1H), 7.93 (d, 1H), 7.90 (m, 2H), 7.81 (dd, 1H), 7.74 (d, 1H), 7.68 (d, 1H), 7.66 (m, 1H), 7.59–7.52 (m, 3H), 7.37 (dd, 1H), 7.25–7.11 (m, 2H), 1.46 (s, 9H), 1.39 (s, 9H), 1.35 (s, 9H).

[0102] Synthesis of compound 72 in Example 5:

[0103]

[0104] Under nitrogen protection, 10 mmol of intermediate a-3, 10 mmol of raw material A-5, 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, 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: 384.19 ([M+H] + )), theoretical value: 383.14.

[0105] Under nitrogen protection, 10 mmol of intermediate a-5, 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 22 hours. After the reaction, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate b-5. LC-MS: Measured value: 627.35 ([M+H] + )), theoretical value: 626.37.

[0106] Under an oxygen atmosphere, 10 mmol of intermediate b-5 and 11 mmol of DMSO were dissolved in 30 ml of ethyl acetate. After heating to 60 °C, 12 mmol of HBr (48% concentration) was added and the reaction was carried out for 8 hours. The reaction system was cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The concentrated reaction solution was separated and purified by column chromatography to obtain intermediate c-5. LC-MS: Measured value: 705.27 ([M+H] + ), theoretical value: 704.28. 1 H NMR (400 MHz, chloroform-d) δ 8.00 - 7.81 (m, 3H), 7.61 - 7.43 (m, 7H), 7.41 - 7.39 (d, 2H), 7.35 - 7.22 (m, 4H), 7.02 - 6.94 (m, 2H), 1.44 - 1.32 (m, 27H).

[0107] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate c-5 and 5 ml of o-dichlorobenzene were added. A solution of 12 mmol of n-butyllithium in n-hexane was added at 0 °C, and the reaction system was heated to 60 °C and reacted for 2 hours. Then, 15 mmol of boron tribromide was added at 0 °C, and the reaction was continued at room temperature for 10 hours. Subsequently, 20 mmol of N,N-diisopropylethylamine was added to the system at 0 °C, and the reaction was heated to 200 °C and reacted for 10 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain compound 72.

[0108] 1 H NMR (400 MHz, chloroform-d) δ 8.34 - 8.30 (m, 1H), 8.17 - 8.11 (m, 2H), 8.06 - 8.01 (m, 2H), 7.98 - 7.95 (m, 1H), 7.90 (d, 1H), 7.78 (d, 1H), 7.71 (d, 1H), 7.55 - 7.50 (m, 2H), 7.47 (m, 1H), 7.41 (t, 1H), 7.29 (dd, 1H), 7.18 (dd, 1H), 7.05 (d, 1H), 1.45 (s, 9H), 1.37 (s, 9H), 1.33 (s, 9H).

[0109] Synthesis of Compound 83 in Example 6:

[0110]

[0111] Under nitrogen protection, 10 mmol of intermediate a-3, 10 mmol of raw material A-6, 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 28 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: 324.18 ([M+H] + ), theoretical value: 323.11.

[0112] Under nitrogen protection, 10 mmol of intermediate a-6, 10 mmol of raw material B-6, 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 25 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: 581.40 ([M+H] + ), theoretical value: 580.35.

[0113] Under oxygen condition, 10 mmol of intermediate b-6 and 11 mmol of DMSO were dissolved in 30 ml of ethyl acetate. After heating to 60 °C, 12 mmol of HBr (48% concentration) was added and the reaction was carried out for 6 hours. The reaction system was cooled to room temperature, and the solvent was removed by distillation under reduced pressure. Then the reaction solution was concentrated and purified by column chromatography to obtain intermediate c-6. LC-MS: Measured value: 659.30 ([M+H] + ), theoretical value: 658.26. 1 H NMR (400 MHz, chloroform-d) δ 8.10 (d, 1H), 7.95 - 7.88 (m, 2H), 7.81 (d, 1H), 7.73 (d, 1H), 7.64 (d, 1H), 7.49 - 7.41 (m, 2H), 7.34 - 7.28 (m, 3H), 7.21 - 7.17 (m, 2H), 2.81 (s, 3H), 1.45 (s, 9H), 1.32 (s, 9H), 1.28 (s, 9H).

[0114] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate c-6 and 5 ml of o-dichlorobenzene were added. At 0 °C, a n-hexane solution of 12 mmol of n-butyllithium was added, the system was heated to 60 °C and reacted for 2 hours. Then at 0 °C, 15 mmol of boron tribromide was added, and the reaction was continued at room temperature for 5 hours. Then the system was added with 20 mmol of N,N-diisopropylethylamine at 0 °C and heated to 200 °C and reacted for 14 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 83.

[0115] 1 1H NMR (400 MHz, chloroform-d) δ 8.15 (d, 1H), 8.02 (d, 1H), 7.91 (d, 1H), 7.79 (d, 1H), 7.65 (s, 1H), 7.44 (t, 1H), 7.35–7.23 (m, 4H), 7.18 (dd, 1H), 2.41 (s, 3H), 1.39 (s, 9H), 1.31 (d, 18H).

[0116] Synthesis of Compound 126 in Example 7:

[0117]

[0118] Under nitrogen protection, 10 mmol of intermediate a-3, 10 mmol of raw material A-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 18 hours. After the reaction was completed, the organic layer was concentrated under reduced pressure and then purified by silica gel column chromatography to obtain intermediate a-7. LC-MS: Measured value: 475.22 ([M+H] + ), theoretical value: 474.19.

[0119] Under nitrogen protection, 10 mmol of intermediate a-7, 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 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-7. LC-MS: Measured value: 718.49 ([M+H] + ), theoretical value: 717.41.

[0120] Under oxygen condition, 10 mmol of intermediate b-7 and 11 mmol of DMSO were dissolved in 30 ml of ethyl acetate. After heating to 60 °C, 12 mmol of HBr (48% concentration) was added and the reaction was carried out for 5 hours. The reaction system was cooled to room temperature, the solvent was removed by distillation under reduced pressure, and the concentrated reaction solution was separated and purified by column chromatography to obtain intermediate c-7. LC-MS: Measured value: 796.31 ([M+H] + ), theoretical value: 795.32. 1 1H NMR (400 MHz, chloroform-d) δ 8.02 (dd, 3H), 7.72 (d, 1H), 7.64 - 7.55 (m, 4H), 7.43 - 7.22 (m, 15H), 1.41 (s, 18H), 1.36 (s, 9H).

[0121] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate c-7 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 4 hours. Then, 15 mmol of boron tribromide was added at 0 °C, and the reaction was continued at room temperature for 3 hours. Subsequently, 20 mmol of N,N-diisopropylethylamine was added to the reaction 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 126.

[0122] 1 H NMR (400 MHz, chloroform-d) δ 8.19 (d, 1H), 7.93 (d, 1H), 7.88 (d, 1H), 7.81 (d, 1H), 7.63 (d, 1H), 7.58–7.55 (m, 3H), 7.51–7.33 (m, 11H), 7.29–7.15 (m, 2H), 1.45 (s, 9H), 1.41 (s, 9H), 1.35 (s, 9H).

[0123] Synthesis of Compound 132 in Example 8:

[0124]

[0125] Under nitrogen protection, 10 mmol of intermediate a-7, 10 mmol of raw material A-8, 15 mmol of potassium carbonate, 0.5 mmol of Pd2(dba)3, 1.5 mmol of 2-dicyclohexylphosphino-2',6'-diisopropoxybiphenyl, and 50 mL of anhydrous o-xylene were added to a three-necked flask 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-8. LC-MS: Measured value: 640.39 ([M+H] + )), theoretical value: 639.36.

[0126] Under oxygen, 10 mmol of intermediate b-8 and 11 mmol of DMSO were dissolved in 30 ml of ethyl acetate. After heating to 60 °C, 12 mmol of HBr (48% concentration) was added and the reaction was carried out for 5 hours. The reaction system was cooled to room temperature, the solvent was removed by distillation under reduced pressure, and the reaction solution was concentrated and separated and purified by column chromatography to obtain intermediate c-8. LC-MS: Measured value: 718.26 ([M+H] + )), theoretical value: 717.27.

[0127] 11H NMR (500 MHz, chloroform-d) δ 8.02 (d, 1H), 7.86 - 7.74 (m, 2H), 7.63 - 7.57 (m, 2H), 7.40 - 7.29 (m, 9H), 7.21 - 7.13 (m, 2H), 7.08 - 6.95 (m, 3H), 6.90 - 6.82 (m, 2H), 2.42 - 2.33 (m, 1H), 2.17 - 2.05 (m, 3H), 1.59 - 1.54 (m, 4H), 1.44 (s, 9H), 1.28 (d, 6H).

[0128] In a sealed pressure-resistant tube, under nitrogen protection, 10 mmol of intermediate c-8 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 2 hours. Then, 15 mmol of boron tribromide was added at 0 °C, and the reaction was continued at room temperature for 8 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 13 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 132.

[0129] 1 1H NMR (400 MHz, chloroform-d) δ 7.91 (d, 1H), 7.77 (d, 1H), 7.59–7.54 (m, 2H), 7.51–7.28 (m, 13H), 7.12 (dd, 1H), 6.99 (t, 1H), 2.25–2.17 (m, 1H), 2.13–1.98 (m, 3H), 1.69–1.55 (m, 4H), 1.39 (s, 9H), 1.35 (d, 6H).

[0130] The structural characterizations of the compounds obtained in each example are shown in Table 1

[0131] Table 1

[0132]

[0133] 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:

[0134] Table 2

[0135]

[0136] 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.

[0137] 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.

[0138] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 1-8 and Device Comparative Examples 1-3. The manufacturing processes of Device Examples 2-8 and Device Comparative Examples 1-3 of the present invention are exactly the same as those of Device Example 1, and the same substrate materials and electrode materials are used, and the film thicknesses of the electrode materials are also kept consistent. The difference is that the light-emitting layer materials in the devices are replaced. The layer structures and test results of each device example are shown in Tables 3-1 and 4 respectively.

[0139] Device Example 1

[0140] As Figure 1 shown, the transparent substrate layer 1 is a transparent PI film. The ITO anode layer 2 (film thickness of 150 nm) is washed, that is, washed with a cleaning agent (Semiclean M-L20), pure water, and dried in sequence, 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 2 is used as a doping material. The mass ratio of GH-1, GH-2, and compound 2 is 69:30:1, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously 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.

[0141] The application effects of the synthesized OLED materials of the present invention in devices are described in detail below through Device Examples 10-17 and Device Comparative Examples 4-6. The manufacturing processes of Device Examples 11-17 and Device Comparative Examples 4-6 are exactly the same as that 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 Table 3-2 and Table 4 respectively

[0142] Device Example 10

[0143] 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, GD-1 is used as the first doping material, and Compound 2 is used as the second doping material. The mass ratio of GH-1, GH-2, GD-1, and Compound 2 is 66:30:3:1, and the film thickness of the light-emitting layer is 30 nm. After the above light-emitting layer 6, HB-1 is continuously 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

[0144] The molecular structural formulas of the related materials are shown as follows:

[0145]

[0146]

[0147] After completing the OLED light-emitting device as described above, the anode and the cathode are connected by a known driving circuit, and the current efficiency, external quantum efficiency, and device lifetime of the device are measured. The device examples and comparative examples prepared by the same method are shown in Tables 3-1 and 3-2; the test results of the current efficiency, external quantum efficiency, and lifetime of the obtained devices are shown in Table 4.

[0148] Table 3-1

[0149]

[0150] Table 3-2

[0151]

[0152]

[0153] Table 4

[0154]

[0155] Note: The voltage, current efficiency, and emission peak are measured using an IVL (current-voltage-luminance) test system (Suzhou FushiDa Scientific Instruments Co., Ltd.); the lifetime test system is the EAS-62C type OLED device lifetime tester of System Technology Research Co., Ltd. of Japan; LT95 refers to the time when the device luminance decays to 95%; all data are tested at 10 mA / cm 2 under.

[0156] From the device data results in Table 4, it can be seen that compared with Comparative Examples 1-3 of the device, the current efficiency and device lifetime of the compound of the present invention in the fluorescent sensitization system device are both higher than those of the comparative examples; in the sensitized phosphorescent system device, the device efficiency also shows good results, which is because such a boron-nitrogen fused ring parent nucleus can enhance the resonance intensity and improve the device efficiency.

[0157] In summary, the above are only the preferred embodiments of the present invention and are not intended to limit the present invention. Any modifications, equivalent replacements, improvements, etc. made within the spirit and principles of the present invention shall be included within the protection scope of the present invention.

Claims

1. A boron-containing resonance-type organic compound, characterized in that, The structure of the organic compound is shown by any one of general formula (1-2) to general formula (1-4), general formula (1-6) to general formula (1-9): In general formula (1-2) to general formula (1-4), general formula (1-6) to general formula (1-9), 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 substituted or unsubstituted C6-C 10 aryloxy 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; X independently represents O, S, N(R3) respectively; R3 is independently represented as a substituted or unsubstituted C6-C 30 aryl, a substituted or unsubstituted C2-C 30 heteroaryl; R a 、R b 、R c 、R d 、R e each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted C1-C 10 alkyl group, a substituted or unsubstituted C3-C 10 cycloalkyl group, a substituted or unsubstituted C6-C 30 aryl group, a substituted or unsubstituted C2-C 30 heteroaryl group; 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 resonance-type organic compound according to any one of claims 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 xanthone group, a phenyl-substituted triazine group, a methoxy group, a tert-butoxy group; R3 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 xanthone group, a phenyl-substituted triazine group; The R a , R b , R c , R d , R e is represented by 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 tert-butyl-substituted dibenzofuryl group, a phenyl-substituted tert-butyl group, an xanthenone group, a phenyl-substituted triazinyl group; The substituents for the substituting groups are each independently selected from a deuterium atom, a halogen atom, an adamantyl group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a 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, an xanthenone group.

3. The boron-containing resonance-type organic compound according to claim 1, characterized in that, The specific structure of the organic compound is any one of the following structures:

4. 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 resonance-type organic compound according to any one of claims 1-3.

5. The organic electroluminescent device according to claim 4, characterized in that, The light-emitting layer comprises a host material and a doping material, and the doping material contains the boron-containing resonance-type organic compound according to any one of claims 1-3.

6. The organic electroluminescent device according to claim 4, 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 resonance-type organic compound according to any one of claims 1-3.

7. The organic electroluminescent device according to claim 4, wherein the light-emitting layer comprises a host material, an exciton sensitizing material, and a doping material, characterized in that, The exciton sensitization material is a metal element-containing complex.

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