阅读说明：本技术 四齿金属络合物及其应用 (Tetradentate metal complex and application thereof ) 是由 鄢亮亮 陈少福 戴雷 蔡丽菲 于 2020-06-16 设计创作，主要内容包括：本发明涉及一种四齿金属络合物及其应用。所述四齿金属络合物具有式(1)所示结构。本发明提供的四齿金属络合物具有光、电、热稳定性好,发光效率高,寿命长,色饱和度高等优点,可用于有机发光器件中,特别是作为绿色发光磷光材料,具有应用于AMOLED产业的可能。(The invention relates to a tetradentate metal complex and application thereof. The tetradentate metal complex has a structure represented by formula (1). The tetradentate metal complex provided by the invention has the advantages of good light, electricity and thermal stability, high luminous efficiency, long service life, high color saturation and the like, can be used in organic light-emitting devices, particularly as a green light-emitting phosphorescent material, and has the possibility of being applied to the AMOLED industry.)

1. A tetradentate metal complex having a structure represented by formula (1)

Wherein:

m is independently Pt or Pd;

X1-X4 are each independently selected from N or CR₀；

L1-L3 are each independently selected from the group consisting of a direct bond, O, S, Se, NRa, CRbRc, SO, SO2, PO (Rd) (Re), SiRfRg, GeRhRi;

R₀R1-R15 and Ra-Ri are each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 arylsilyl, substituted or unsubstituted C0-C20 amine, cyano, nitrile, isonitrile, phosphino, or any two adjacent substituents can be linked to each other to form a cyclic structure or a ring structure, said substitution is by deuterium, halogen or C1-C4 alkyl; the heteroatom in the heteroalkyl or heteroaryl group is any one or more of S, O, N.

2. The tetradentate metal complex according to claim 1, which has a structure represented by formula (2)

Wherein X1-X4, R1-R4, R7-R15 are as defined above.

3. The tetradentate metal complex of claim 2, which has a structure represented by formula (3):

wherein

R1-R4, R7, R8, R10-R15 are as defined above.

4. A tetradentate metal complex as claimed in claim 3, wherein R7, R8, R10, R11 are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C8 heteroalkyl, substituted or unsubstituted C7-C10 aralkyl, substituted or unsubstituted C6-C10 aryl or substituted or unsubstituted C3-C10 heteroaryl.

5. The tetradentate metal complex of claim 4, wherein at least one of R7, R8, R10, and R11 is not hydrogen.

6. The tetradentate metal complex of claim 3, wherein R15 is independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl.

7. The tetradentate metal complex of claim 6, wherein R15 is benzene or represented by structural formula (9) or formula (10);

wherein

Indicates the position of the connection;

z5 is O, S, Se, NR₁₀₅，CR₁₀₆R₁₀₇，SO，SO2，PO(R₁₀₈)(R₁₀₉)，SiR₁₁₀R₁₁₁，，GeR₁₁₂R₁₁₃，；

R₁₀₁-R₁₀₄The number of (2) is expressed as a maximum algebraic number;

l4, L5 are single bonds, substituted or unsubstituted C1-C20 alkylene, substituted or unsubstituted C3-C30 cycloalkylene, substituted or unsubstituted C1-C20 heteroalkylene, substituted or unsubstituted C7-C30 aralkylene, substituted or unsubstituted C2-C20 alkenylene, substituted or unsubstituted C3-C30 alkylenesilyl, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene, substituted or unsubstituted C3-C30 arylsilyl, substituted or unsubstituted C0-C20 imino;

R₁₀₁-R₁₁₃each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 arylsilyl, substituted or unsubstituted C0-C20 amine, cyano, nitrile, isonitrile, phosphine, or any two adjacent substituents can be linked to each other to form a ring structure or ring structure, said substitution is by deuterium, halogen or C1-C4 alkyl; the heteroatom in the heteroalkyl or heteroaryl group is any one or more of S, O, N.

8. The tetradentate metal complex of claim 7, Z5 is O, NR₁₀₅Or CR₁₀₆R₁₀₇，

L4 and L5 are single bonds,

R₁₀₁-R₁₀₇each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C8 heteroalkyl, substituted or unsubstituted C7-C10 aralkyl, substituted or unsubstituted C6-C10 aryl, and substituted or unsubstituted C3-C10 heteroaryl.

9. The tetradentate metal complex according to any one of claims 1-8, wherein R12 and R13, or R13 and R14 are linked to form one of the fused ring structures represented by the following formulae (4) to (7);

wherein:

indicates the position of the connection;

Z₁-Z₃selected from O, S, Se, NRx or CRyRz;

Y₁-Y₁₂identical or different at each occurrence is CR₀Or N;

R₀rx, Ry, Rz are each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 silylaryl, substituted or unsubstituted C0-C20 amine, cyano, nitrile, isonitrile, phosphine, or any two adjacent substituents can be linked to each other to form a cyclic structure or a ring structure, said substitution is by deuterium, halogen or C1-C4 alkyl; the heteroatom in the heteroalkyl or heteroaryl group is any one or more of S, O, N.

10. The tetradentate metal complex of claim 9, where Z₁-Z₃Selected from O, NRx or CRyRz;

Y₁-Y₁₂identical or different at each occurrence is CR₀Or N;

R₀rx, Ry, Rz are each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C8 heteroalkyl, substituted or unsubstituted C7-C10 aralkyl, substituted or unsubstituted C6-C10 aryl, or substituted or unsubstituted C3-C10 heteroaryl.

11. The metal complex of claim 9, wherein at least one of R1 and R2 is not hydrogen.

12. The tetradentate metal complex according to claim 9, wherein R1 and R2, or R2 and R3, or R3 and R4 are linked to form a fused ring structure represented by formula (8);

wherein:

indicates the position of the connection;

Z₄represents O, S, Se, NR₂₀₁，CR₂₀₂R₂₀₃，SO，SO2，PO(R₂₀₄)(R₂₀₅)，SiR₂₀₆R₂₀₇，GeR₂₀₈R₂₀₉；

Y₁₃-Y₁₆Identical or different at each occurrence is CR₀Or N;

R₀、R₂₀₁-R₂₀₉each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 arylsilyl, substituted or unsubstituted C0-C20 amine, cyano, nitrile, isonitrile, phosphino, or any two adjacent substituents can be linked to each other to form a cyclic or fused ring structure; said substitution is by deuterium, halogen or C1-C4 alkyl; the heteroatom in the heteroalkyl or heteroaryl group is any one or more of S, O, N.

13. The tetradentate metal complex, Z, of claim 12₄Represents O, NR₂₀₁Or CR₂₀₂R₂₀₃；

Y₁₃-Y₁₆Identical or different at each occurrence is CR₀Or N;

R₀、R₂₀₁-R₂₀₉each independently selected fromHydrogen, deuterium, halogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C8 heteroalkyl, substituted or unsubstituted C7-C10 aralkyl, substituted or unsubstituted C1-C8 alkoxy, substituted or unsubstituted C6-C10 aryloxy, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C3-C10 heteroaryl.

14. The tetradentate metal complex of claim 1, which is one of the following structural formulae;

15. an electroluminescent device, comprising: a cathode, an anode, and an organic layer disposed between the cathode and the anode, at least one of the organic layers comprising the tetradentate metal complex of any one of claims 1-14.

16. The electroluminescent device of claim 15, wherein the organic layer is a light emitting layer and the tetradentate metal complex is a doping material for a light emitting material in the light emitting layer, or the organic layer is a hole injecting layer and the tetradentate metal complex is a hole injecting material for the hole injecting layer.

17. The device of claim 16, wherein the luminescent material is a green luminescent material, a yellow luminescent material, or a red luminescent material.

Technical Field

The invention relates to the technical field of organic electroluminescence, in particular to an organic luminescent material, and especially relates to a tetradentate metal complex and application thereof in an organic electroluminescent device.

Background

At present, organic electroluminescent devices (OLEDs), which are a new generation of display technologies, are gaining more and more attention in display and lighting technologies, and have a very broad application prospect. However, the performance of OLED devices, such as light emission efficiency, driving voltage, and lifetime, is still in need of further enhancement and improvement compared to market application requirements.

Generally, the OLED device has a basic structure in which various organic functional material thin films with different functions are sandwiched between metal electrodes, as a sandwich structure, and holes and electrons are respectively injected from a cathode and an anode under the driving of current, and after the holes and the electrons move for a certain distance, they are recombined in a light emitting layer and released in the form of light or heat, thereby generating light emission of the OLED. However, the organic functional material is a core component of the organic electroluminescent device, and the thermal stability, photochemical stability, electrochemical stability, quantum yield, film forming stability, crystallinity, color saturation and the like of the material are main factors influencing the performance of the device. Generally, the organic functional material includes a fluorescent material and a phosphorescent material. The fluorescent material is usually an organic small molecule material, and generally can only emit light by using 25% singlet state, so that the luminous efficiency is low. The phosphorescent material can utilize the energy of 75% triplet excitons in addition to 25% singlet state due to the spin-orbit coupling effect caused by the heavy atom effect, so that the luminous efficiency can be improved. However, compared to fluorescent materials, phosphorescent materials start late, and thermal stability, lifetime, color saturation, etc. of the materials are all to be improved, which is a challenging issue. Various organometallic compounds have been developed as such phosphorescent materials. For example, patent document US20180130964 discloses a class of complexes of pt (oncn) with pyridine imidazole attached as red phosphorescent materials. However, development of new materials that can further improve the performance of the organic electroluminescent device is still desired.

Disclosure of Invention

The present invention provides a metal complex containing a structure represented by the following formula (1) as a tetradentate ligand, which can provide a high-performance organic electroluminescent device.

The metal complex has the advantages of light, high electrochemical stability, high color saturation, high luminous efficiency, long service life of the device and the like, and can be used in organic electroluminescent devices. Particularly as a green emitting dopant, has potential for application in the OLED industry.

In order to achieve the purpose, the invention adopts the following technical scheme:

a tetradentate metal complex having a structure represented by formula (1)

Wherein

M is independently Pt or Pd;

X1-X4 are each independently selected from N or CR₀；

L1-L3 are each independently selected from the group consisting of a direct bond, O, S, Se, NRa, CRbRc, SO, SO2, PO (Rd) (Re), SiRfRg, GeRhRi;

R₀R1-R15 and Ra-Ri are each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 arylsilyl, substituted or unsubstituted C0-C20 amine, cyano, nitrile, isonitrile, phosphino, or any two adjacent substituents can be linked to each other to form a cyclic structure or a ring structure, said substitution is by deuterium, halogen or C1-C4 alkyl; the heteroatom in the heteroalkyl or heteroaryl group is any one or more of S, O, N. (I understand here that any adjacency means R₀R1-R15 and Ra-Ri are adjacent to each other, or the group is limited, and is selected in parallel with the previous scheme, so that "or" is necessary)

Preferably: it has a structure shown in formula (2)

Wherein X1-X4, R1-R4, R7-R15 are as defined above.

More preferably: it has a structure represented by formula (3):

wherein R1-R4, R7, R8, R10-R15 are as defined above.

Further preferably: wherein R7, R8, R10, R11 are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C8 heteroalkyl, substituted or unsubstituted C7-C10 aralkyl, substituted or unsubstituted C6-C10 aryl, or substituted or unsubstituted C3-C10 heteroaryl.

Further preferably: wherein at least one of R7, R8, R10 and R11 is not hydrogen.

Further preferably: wherein R15 is independently selected from substituted or unsubstituted C6-C30 aryl or substituted or unsubstituted C3-C30 heteroaryl.

Further preferably: wherein R15 is benzene or represented by structural formula (9) or formula (10);

wherein:

indicates the position of the connection;

z5 is O, S, Se, NR₁₀₅，CR₁₀₆R₁₀₇，SO，SO2，PO(R₁₀₈)(R₁₀₉)，SiR₁₁₀R₁₁₁，，GeR₁₁₂R₁₁₃，；

R₁₀₁-R₁₀₄The number of (2) is expressed as a maximum algebraic number;

l4, L5 are single bonds, substituted or unsubstituted C1-C20 alkylene, substituted or unsubstituted C3-C30 cycloalkylene, substituted or unsubstituted C1-C20 heteroalkylene, substituted or unsubstituted C7-C30 aralkylene, substituted or unsubstituted C2-C20 alkenylene, substituted or unsubstituted C3-C30 alkylenesilyl, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene, substituted or unsubstituted C3-C30 arylsilyl, substituted or unsubstituted C0-C20 imino;

R₁₀₁-R₁₁₃each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 arylsilyl, substituted or unsubstituted C0-C20 amine, cyano, nitrile, isonitrile, phosphine, or any two adjacent substituents can be linked to each other to form a ring structure or ring structure, said substitution is by deuterium, halogen or C1-C4 alkyl; the heteroatom in the heteroalkyl or heteroaryl group is any one or more of S, O, N.

Further preferably: z5 is O, NR₁₀₅Or CR₁₀₆R₁₀₇，

L4 and L5 are single bonds,

R₁₀₁-R₁₀₇each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C8 heteroalkyl, substituted or unsubstituted C7-C10 aralkyl, substituted or unsubstituted C6-C10 aryl, and substituted or unsubstituted C3-C10 heteroaryl.

Further preferably: wherein R12 and R13, or R13 and R14 are linked to form one of the parallel ring structures shown in the following formulae (4) to (7);

wherein

Indicates the position of the connection;

Z₁-Z₃selected from O, S, Se, NRx or CRyRz;

Y₁-Y₁₂identical or different at each occurrence is CR₀Or N;

R₀rx, Ry, Rz are each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 silylaryl, substituted or unsubstituted C0-C20 amine, cyano, nitrile, isonitrile, phosphine, or any two adjacent substituents can be linked to each other to form a cyclic structure or a ring structure, said substitution is by deuterium, halogen or C1-C4 alkyl; the heteroatom in the heteroalkyl or heteroaryl group is any one or more of S, O, N.

Further preferably: wherein Z₁-Z₃Selected from O, NRx or CRyRz;

Y₁-Y₁₂identical or different at each occurrence is CR₀Or N;

R₀rx, Ry, Rz are each independently selected from hydrogen, halogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C8 heteroalkyl, substituted or unsubstituted C7-C10 aralkyl, substituted or unsubstituted C6-C10 aryl, or substituted or unsubstituted C3-C10 heteroaryl.

Further preferably: wherein at least one of R1 and R2 is not hydrogen.

Further preferably: wherein R1 and R2, or R2 and R3, or R3 and R4 are connected to form a fused ring structure shown in formula (8);

wherein

Indicates the position of the connection;

Z₄represents O, S, Se, NR₂₀₁，CR₂₀₂R₂₀₃，SO，SO2，PO(R₂₀₄)(R₂₀₅)，SiR₂₀₆R₂₀₇，GeR₂₀₈R₂₀₉；

Y₁₃-Y₁₆Identical or different at each occurrence is CR₀Or N;

R₀、R₂₀₁-R₂₀₉each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C20 heteroalkyl, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C3-C30 alkylsilyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, substituted or unsubstituted C3-C30 arylsilyl, substituted or unsubstituted C0-C20 amine, cyano, nitrile, isonitrile, phosphino, or any two adjacent substituents can be linked to each other to form a cyclic or fused ring structure; said substitution is by deuterium, halogen or C1-C4 alkyl; the heteroatom in the heteroalkyl or heteroaryl group is any one or more of S, O, N.

Further preferably: z₄Represents O, NR₂₀₁Or CR₂₀₂R₂₀₃；

Y₁₃-Y₁₆Identical or different at each occurrence is CR₀Or N;

R₀、R₂₀₁-R₂₀₉each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C8 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C8 heteroalkyl, substituted or unsubstituted C7-C10 aralkyl, substituted or unsubstituted C1-C8 alkoxy, substituted or unsubstituted C6-C10 arylateOxy, substituted or unsubstituted C6-C10 aryl, substituted or unsubstituted C3-C10 heteroaryl.

As the preferred metal complex, among them, the following structural formula is preferred;

one of the objects of the present invention is an electroluminescent device comprising: a cathode, an anode, and an organic layer disposed between the cathode and the anode, at least one of the organic layers comprising a tetradentate metal complex.

An object of the present invention is also an electroluminescent device, wherein the organic layer is a light-emitting layer, the metal complex is used as a doping material for a light-emitting material, in particular as a doping material for a green light-emitting material;

an object of the present invention is also an electroluminescent device, wherein the organic layer is a light-emitting layer, the metal complex is used as a doping material for a light-emitting material, in particular as a doping material for a yellow light-emitting material;

an object of the present invention is also an electroluminescent device, wherein the organic layer is a light-emitting layer, and the metal complex is used as a light-emitting material doping material, particularly as a red light-emitting doping material;

it is also an object of the invention to provide an electroluminescent device wherein the organic layer is a hole injection layer and the metal complex is used as a hole injection material.

Detailed Description

The examples are only for the convenience of understanding the technical invention and should not be construed as specifically limiting the invention.

The raw materials and solvents involved in the synthesis of the compounds of the invention are commercially available from suppliers well known to those skilled in the art, such as Alfa, Acros, and the like.

EXAMPLE 1 Synthesis of Compound CPD1

Synthesis of intermediate A1

Synthesis of Compound A1-3

A1-1(100.0g, 0.36mol, 1.0eq), A1-2(137.7g, 0.72mol, 2.0eq), sodium bicarbonate (45.3g, 0.54mol, 1.5eq), and ethanol (1L) were added in this order to A3L three-necked flask, stirred, replaced with nitrogen gas under vacuum three times, and heated to reflux for 2 h. TLC monitoring (developing solvent: ethyl acetate/n-hexane 1/10) almost completed consumption of starting material a 1-1. Cooling the reaction solution to room temperature, slowly inverting the reaction solution, stirring the reaction solution in 1L of water under stirring at room temperature for 2h, filtering, and leaching a filter cake with acetonitrile/n-hexane (1/4) for 3 times, wherein the total amount is 0.5L. It was dried by suction to give A1-3(83.5g, yield 85.0%) as a pale yellow solid. Mass spectrum: 274.3(M + H)

Synthesis of Compound A1-4

A1-3(83.5g, 0.30mol,1.0eq) and acetonitrile (1.6L) were added in this order to a 3L three-necked flask and stirred. N-iodosuccinimide (72.2g, 0.32mol, 1.06eq) was added portionwise at room temperature and stirred for 30 minutes at room temperature. As the reaction proceeded, the reaction solution gradually turned white from pale yellow. TLC monitoring (developing solvent: ethyl acetate/n-hexane 1/15) almost completed consumption of the starting material a 1-3. Deionized water (330ml) was added to the reaction solution, and the mixture was stirred for 1 hour. Filtration, rinsing the filter cake twice with a total of 200ml of acetonitrile/water 4/1 and pump-drying the material to give a white solid a1-4(110g, yield 90.2%). Mass spectrum: 400.2 Synthesis of (M + H) Compound A1-5

A1-4(110g, 0.27mol,1.0eq), phenylboronic acid (35.2g, 0.28mol,1.03), dioxane (1.7L), KOH (30.9g, 0.55mol, 2.0eq), and deionized water (300ml) were added to a 5L three-necked flask in this order, and Pd (PPh) was added after replacing with nitrogen for 3 times₃)₄(3.19g, 2.76mmol, 0.01eq), replaced with nitrogen three times, and then heated to 85 ℃ for reaction. As the reaction proceeded, the reaction solution became clear from turbid. Monitored by TLC (developing solvent: ethyl acetate/n-hexane: 1/20), a1-4 was essentially completely consumed. The temperature of the reaction solution was reduced to 60-70 deg.C, and the reaction solution was slowly poured into stirred ice water (2L) and stirred for 1.5 h. After filtration, a yellow solid was collected, dissolved in dichloromethane (1.2L), passed through silica gel and rinsed with a small amount of dichloromethane, the filtrate was concentrated to 100ml of solvent, and n-hexane (500ml) was added and stirred at room temperature for 1 hour. The resulting yellow solid was filtered, slurried with toluene (100ml) and n-hexane (500ml) and stirred for 1 h. Filtration and drying gave A1-5 as a white solid (70.3g, 73.1% yield). Mass spectrum: 350.2(M + H)

Synthesis of Compound A1

In a 1L single vial, compound a1-5(70.0g, 0.20mol, 1.0eq), pinacol diboride (61.0g, 0.24mol, 1.2eq), [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (2.93g, 4.01mmol, 0.02eq), potassium acetate (39.3g, 0.4mol, 2.0eq), dioxane (560ml) were sequentially subjected to nitrogen substitution, then heated to 100 ℃, kept under constant temperature and stirred for 6 hours, monitored by TLC (developing agent: ethyl acetate/n-hexane 1/10), and the starting material a1-5 was substantially completely reacted. The reaction solution was cooled to 40 ℃ and filtered through celite, the filter cake was washed with a small amount of dioxane, the filtrate was concentrated under reduced pressure to 200ml, methanol (400ml) was added and stirred at room temperature for 2h, the filtrate was filtered to give a solid, n-hexane (400ml) was added and slurried at 50 ℃ for 2h, and the solid was filtered and dried to give off-white solid compound a1(57.4g, yield 72.3%). Mass spectrum: 397.2(M + H).

Synthesis of Compound CPD1

Synthesis of Compound CPD1-3

CPD1-1(14.5g, 64.71mmol, 1.0eq), CPD1-2(8.36g, 55.0mmol, 0.85eq), [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (2.37g, 3.24mmol, 0.05eq), sodium carbonate (13.72g, 129.4mmol, 2.0eq), acetonitrile (218ml), deionized water (55ml) were added in this order to a 500ml three-necked flask, the apparatus was deoxygenated 3 times, nitrogen was purged, and then heated to 85 ℃ for reaction for 2 hours, and TLC plates (developing agent: ethyl acetate/n-hexane 1/15) and a small amount of CPD1-3 remained to terminate the reaction. The reaction solution was rotary evaporated to remove the organic solvent, dichloromethane (300mL) was added and stirred to dissolve, deionized water (150mL) was added to extract the separated liquid, the aqueous phase was further extracted with dichloromethane (100mL) for 1 time, the organic phases were combined, and the rotary dried black crude product was purified by column chromatography (eluent: ethyl acetate/n-hexane: 1/30) to give CPD1-3(12.48g, yield 65.2%) as a white solid. Mass spectrum: 296.8(M + H).

Synthesis of Compound CPD1-4

CPD1-3(12.2g, 41.2mmol, 1.0eq), A1(17.16g, 43.3mmol, 1.0eq), [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (1.51g, 2.06mmol, 0.05eq), cesium carbonate (26.88g, 82.5mmol, 2.0eq), dioxane (120ml) and deionized water (24ml) were added in this order to a 500ml three-necked flask, the apparatus was deoxygenated 3 times, nitrogen was purged, and then heated to 70 ℃ for reaction for 5 hours, a TLC point plate (developing agent: ethyl acetate/n-hexane 1/3) was used, and CPD1-3 was almost completely consumed, and the reaction was terminated. And cooling the reaction solution to room temperature, adding deionized water (60ml) and toluene (100ml), stirring, separating, collecting an organic phase, filtering by silica gel, leaching a filter cake by using a small amount of toluene, and spin-drying the filtrate to obtain a brown crude product. The crude product was recrystallized from toluene (80 ml)/methanol (240ml) 2 times, filtered and dried to give CPD1-4 as a white solid (14.09g, 64.5% yield). Mass spectrum: 530.6(M + H).

Synthesis of Compound CPD1-5

CPD1-4(14g, 26.43mmol,1.0eq), pyridine hydrochloride (146g, 1.27mol, 48eq), was charged into a 500mL single-neck flask, dichlorobenzene (32mL) was added, the mixture was stirred, nitrogen was replaced four times, the temperature was raised to 190 ℃ and the reaction was carried out for 2.5h, followed by TLC monitoring (developing solvent: ethyl acetate/n-hexane 1/3), the starting materials were reacted completely, and the reaction was cooled to room temperature. To the reaction, saturated sodium bicarbonate solution (150ml) and toluene (150ml) were added, the clear solution was stirred, the organic phase was washed with water 2 times (150 ml/time), and the organic phase was collected and spin-dried. The crude product was recrystallized from toluene (60 ml)/n-hexane (180ml) for 2 times, filtered and dried to give CPD1-5 as a pale yellow solid (11.7g, 86.2% yield). Mass spectrum: 515.6(M + H).

Synthesis of Compound CPD1

A1L single-neck flask was charged with CPD1-5(6.5g, 12.61mmol,1.0eq), potassium chloroplatinite (8.11g, 19.54mmol,1.55eq), tetrabutylammonium bromide (280mg,1.9mmol,0.15eq) and acetic acid (650 ml). Vacuum and nitrogen replacement are carried out for three times, and the mixture is heated to 125 ℃ under the protection of nitrogen for reaction for 72 hours. TLC monitoring (developing solvent: dichloromethane/n-hexane: 1/2), the raw material CPD1-5 completely reacts, and the reaction is cooled to room temperature. The reaction solution was added to a beaker containing deionized water (650ml), and the solid was precipitated by stirring and collected by filtration. The crude product was subjected to silica gel column chromatography (eluent: dichloromethane/n-hexane-1/5), and the resulting orange solid was recrystallized from dichloromethane (50 ml)/methanol (75ml) 1 time to give the orange compound CPD1(5.5g, yield 62.1%). Sublimation purification of 5.5g crude CPD1 gave sublimed pure CPD1(3.61g, yield 65.6%) mass spectrum: 708.7(M + H).¹HNMR(400MHz,CDCl₃)δ8.65(m,1H),8.48(dd,1H),8.26(dd,1H),8.20(s,2H),7.86(m,J＝15.0Hz,3H),7.73(m,J＝25.0Hz,3H),7.62–7.35(m,7H),7.29(m,J＝5.0Hz,2H),7.21(m,1H),6.97(m,1H),6.86(m,1H).

EXAMPLE 2 Synthesis of Compound CPD5

Synthesis of Compound CPD 5-2:

the synthesis process and the post-treatment purification method of the reference compound CPD1-3 only need to change the corresponding raw materials. Mass spectrum: 409.1(M + H).

Synthesis of Compound CPD 5-3:

the synthesis process and the post-treatment purification method of the reference compound CPD1-4 only need to change the corresponding raw materials. Mass spectrum: 642.8(M + H).

Synthesis of Compound CPD 5-4:

the synthesis process and the post-treatment purification method of the reference compound CPD1-5 only need to change the corresponding raw materials. Mass spectrum: 628.8(M + H).

Synthesis of compound CPD 5:

referring to the synthesis process and the post-treatment purification method of the compound CPD1, only the corresponding raw materials need to be changed, and the orange compound CPD5(4.31g, yield 58.8%) is obtained. Sublimation purification of 4.31g crude CPD5 gave pure CPD5(2.85g, 66.1% yield). Mass spectrum: 821.8(M + H).¹HNMR(400MHz,CDCl₃)δ8.68(m,1H),8.46(dd,1H),8.28(dd,1H),8.22(s,2H),7.87(m,J＝15.0Hz,3H),7.72(dd,J＝15.0Hz,3H),7.52(m,J＝22.5,7.5Hz,5H),7.29(d,J＝5.0Hz,2H),7.21(t,1H),6.97(m,1H),6.86(t,1H),1.32(s,18H).

EXAMPLE 3 Synthesis of Compound CPD10

Synthesis of Compound CPD 10-2:

the synthesis process and the post-treatment purification method of the reference compound CPD1-3 only need to change the corresponding raw materials. Mass spectrum: 423.0(M + H).

Synthesis of Compound CPD 10-3:

the synthesis process and the post-treatment purification method of the reference compound CPD1-4 only need to change the corresponding raw materials. Mass spectrum: 656.9(M + H).

Synthesis of Compound CPD 10-4:

the synthesis process and the post-treatment purification method of the reference compound CPD1-5 only need to change the corresponding raw materials. Mass spectrum: 642.8(M + H).

Synthesis of compound CPD 10:

referring to the synthesis process and the post-treatment purification method of the compound CPD1, only the corresponding raw materials need to be changed, and the orange compound CPD10(4.87g, yield 60.1%) is obtained. Sublimation purification of 4.87g crude CPD10 gave pure CPD10(2.77g, 56.8% yield). Mass spectrum: 835.9(M + H).¹HNMR(400MHz,CDCl₃)δ8.55(dd,1H),8.48(dd,1H),8.26(dd,1H),8.20(s,2H),7.86(m,J＝15.0Hz,3H),7.71(m,J＝15.0Hz,3H),7.52(m,J＝22.5,7.5Hz,5H),7.21(t,1H),7.15(d,1H),7.02(t,1H),6.86(m,1H),2.15(s,3H),1.32(s,18H).

EXAMPLE 4 Synthesis of Compound CPD20

Synthesis of Compound CPD 20-2:

CPD20-1(15.6g, 53.95mmol, 1.0eq), N-dimethylformamide (160ml), potassium carbonate (11.18g, 80.92mmol, 1.5eq) were added to a 500ml three-necked flask, the apparatus was deoxygenated 3 times, nitrogen purged, stirred at room temperature for 30min, iodomethane (9.19g, 64.74mmol, 1.2eq) was added in portions, the reaction was stirred at room temperature overnight, a TLC spot plate (developing solvent: dichloromethane/N-hexane 1/15) was added, and CPD20-1 was essentially completely consumed. Deionized water (200ml) was added to the reaction, stirred for 1h and filtered to collect the solid. The resulting solid was recrystallized 2 times from dichloromethane (90 ml)/methanol (180ml) to give CPD20-2 as an off-white solid (12.86g, 78.6% yield). Mass spectrum: 304.2(M + H).

Synthesis of Compound CPD 20-3:

referring to the synthesis process and the post-treatment purification method of the compound A1, only the corresponding raw materials need to be changed. Mass spectrum: 351.3(M + H).

Synthesis of Compound CPD 20-4:

the synthesis process and the post-treatment purification method of the reference compound CPD1-3 only need to change the corresponding raw materials. Mass spectrum: 525.1(M + H).

Synthesis of Compound CPD 20-5:

the synthesis process and the post-treatment purification method of the reference compound CPD1-4 only need to change the corresponding raw materials. Mass spectrum: 759.0(M + H).

Synthesis of Compound CPD 20-6:

the synthesis process and the post-treatment purification method of the reference compound CPD1-5 only need to change the corresponding raw materials. Mass spectrum: 744.0(M + H).

Synthesis of compound CPD 20:

referring to the synthesis process and the post-treatment purification method of the compound CPD1, only the corresponding raw materials need to be changed, and the orange compound CPD20(4.32g, yield 63.2%) is obtained. Sublimation purification of 4.32g crude CPD20 gave sublimation pure CPD20(2.68g, 62.0% yield). Mass spectrum: 936.3(M + H).¹HNMR(400MHz,CDCl₃)δ8.48(dd,1H),8.26(dd,1H),8.20(s,2H),8.00(d,1H),7.96–7.80(m,4H),7.76–7.60(m,4H),7.52(m,J＝22.5,7.5Hz,5H),7.34(dd,2H),7.23(m,J＝16.4Hz,2H),6.86(m,1H),1.69(s,6H),1.32(s,18H).

EXAMPLE 5 Synthesis of Compound CPD35

Synthesis of intermediate A2

Synthesis of Compound A2-2:

referring to the synthetic process and the post-treatment purification method of the compound A1-3, only the corresponding raw materials need to be changed. Mass spectrum: 324.2(M + H).

Synthesis of Compound A2-3:

referring to the synthetic process and the post-treatment purification method of the compound A1-4, only the corresponding raw materials need to be changed. Mass spectrum: 450.1(M + H).

Synthesis of Compound A2-4:

referring to the synthetic process and the post-treatment purification method of the compound A1-5, only the corresponding raw materials need to be changed. Mass spectrum: 400.3(M + H).

Synthesis of compound a 2:

referring to the synthesis process and the post-treatment purification method of the compound A1, only the corresponding raw materials need to be changed. Mass spectrum: 447.3(M + H).

Synthesis of Compound CPD35

Synthesis of Compound CPD 35-1:

the synthesis process and the post-treatment purification method of the reference compound CPD1-4 only need to change the corresponding raw materials. Mass spectrum: 692.9(M + H).

Synthesis of Compound CPD 35-2:

the synthesis process and the post-treatment purification method of the reference compound CPD1-5 only need to change the corresponding raw materials. Mass spectrum: 678.9(M + H).

Synthesis of compound CPD 35:

referring to the synthesis process and the post-treatment purification method of the compound CPD1, only the corresponding raw materials need to be changed, and the orange compound CPD35(5.1g, yield 65.1%) is obtained. Sublimation purification of 5.1g crude CPD35 gave sublimed pure CPD35(3.02g, 59.2% yield). Mass spectrum: 871.9(M + H).¹HNMR(400MHz,CDCl₃)δ8.97(m,1H),8.65(m,1H),8.48(dd,1H),8.20(s,2H),7.84(m,3H),7.73(d,2H),7.60–7.43(m,7H),7.34–7.15(m,3H),6.97(m,2H),6.86(m,1H),1.32(s,18H).

EXAMPLE 6 Synthesis of Compound CPD40

Synthesis of intermediate A3

Synthesis of Compound A3-2:

a3-1(13.2g, 45.66mmol, 1.0eq) and dichloromethane (105ml) were added in this order to a 500ml three-necked flask, and sufficiently dissolved with stirring. Acetic acid (14ml) was then added at room temperature and bromine (7.66g, 47.94mmol, 1.05eq) was added slowly dropwise via addition funnel and after 3h of reaction, the TLC plate (developing solvent DCM/Hex ═ 1/5) was essentially completely consumed A3-1. After slowly adding 10% sodium bisulfite (150ml) solution and stirring for 0.5h, separating to collect organic phase, washing with deionized water for 3 times (100 ml/time) until the aqueous phase is nearly neutral, concentrating to obtain solid, pulping with n-hexane (250ml) for 2h, filtering, rinsing the solid with a small amount of n-hexane, and drying to obtain white solid (13.64g, yield 81.2%). Mass spectrum: 369.0(M + H).

Synthesis of Compound A3-3:

referring to the synthetic process and the post-treatment purification method of the compound A1-3, only the corresponding raw materials need to be changed. Mass spectrum: 364.2(M + H).

Synthesis of Compound A3-4:

referring to the synthetic process and the post-treatment purification method of the compound A1-4, only the corresponding raw materials need to be changed. Mass spectrum: 490.1(M + H).

Synthesis of Compound A3-5:

referring to the synthetic process and the post-treatment purification method of the compound A1-5, only the corresponding raw materials need to be changed. Mass spectrum: 440.3(M + H).

Synthesis of compound a 3:

referring to the synthesis process and the post-treatment purification method of the compound A1, only the corresponding raw materials need to be changed. Mass spectrum: 487.4(M + H).

Synthesis of Compound CPD40

Synthesis of Compound CPD 40-1:

the synthesis process and the post-treatment purification method of the reference compound CPD1-4 only need to change the corresponding raw materials. Mass spectrum: 732.9(M + H).

Synthesis of Compound CPD 40-2:

the synthesis process and the post-treatment purification method of the reference compound CPD1-5 only need to change the corresponding raw materials. Mass spectrum: 718.9(M + H).

Synthesis of compound CPD 40:

referring to the synthesis process and the post-treatment purification method of the compound CPD1, only the corresponding raw materials need to be changed, and the orange compound CPD40(4.69g, yield 59.1%) is obtained. Sublimation purification of 4.69g crude CPD40 gave pure CPD40(2.84g, 60.6% yield). Mass spectrum: 912.0(M + H).¹HNMR(400MHz,CDCl₃)δ8.65(m,1H),8.48(dd,1H),8.20(s,2H),7.98(dd,1H),7.84(m,2H),7.73(d,2H),7.63–7.45(m,6H),7.44–7.15(m,5H),6.97(m,2H),6.86(m,1H),1.32(s,18H).

EXAMPLE 7 Synthesis of Compound CPD55

Synthesis of intermediate A4

Synthesis of Compound A4-2:

referring to the synthetic process and the post-treatment purification method of the compound A1-3, only the corresponding raw materials need to be changed. Mass spectrum: 316.2(M + H).

Synthesis of Compound A4-3:

referring to the synthetic process and the post-treatment purification method of the compound A1-4, only the corresponding raw materials need to be changed. Mass spectrum: 442.1(M + H).

Synthesis of Compound A4-4:

referring to the synthetic process and the post-treatment purification method of the compound A1-5, only the corresponding raw materials need to be changed. Mass spectrum: 392.3(M + H).

Synthesis of compound a 4:

referring to the synthesis process and the post-treatment purification method of the compound A1, only the corresponding raw materials need to be changed. Mass spectrum: 438.4(M + H).

Synthesis of Compound CPD55

Synthesis of Compound CPD 55-2:

the synthesis process and the post-treatment purification method of the reference compound CPD1-3 only need to change the corresponding raw materials. Mass spectrum: 451.1(M + H).

Synthesis of Compound CPD 55-3:

the synthesis process and the post-treatment purification method of the reference compound CPD1-4 only need to change the corresponding raw materials. Mass spectrum: 727.0(M + H).

Synthesis of Compound CPD 55-4:

the synthesis process and the post-treatment purification method of the reference compound CPD1-5 only need to change the corresponding raw materials. Mass spectrum: 718.9(M + H).

Synthesis of compound CPD 55:

referring to the synthesis process and the post-treatment purification method of the compound CPD1, only the corresponding raw materials need to be changed, and the orange compound CPD55(5.11g, yield 67.2%) is obtained. Sublimation purification of 5.11g crude CPD55 gave pure CPD55(3.21g, 62.8% yield). Mass spectrum: 906.0(M + H).¹HNMR(400MHz,CDCl₃)δ8.55(dd,1H),8.46(dd,1H),8.26(dd,1H),8.20(s,2H),7.86(m,J＝15.0Hz,3H),7.71(m,J＝15.0Hz,3H),7.60–7.39(m,5H),7.22(dd,1H),7.07(t,1H),6.77(t,1H),3.05(tq,1H),2.87(tq,1H),1.32(s,18H),1.15(t,J＝15.0Hz,12H).

EXAMPLE 8 Synthesis of Compound CPD60

Synthesis of intermediate A5

Synthesis of Compound A5-2:

referring to the synthetic process and the post-treatment purification method of the compound A1-3, only the corresponding raw materials need to be changed. Mass spectrum: 414.3(M + H).

Synthesis of Compound A5-3:

referring to the synthetic process and the post-treatment purification method of the compound A1-4, only the corresponding raw materials need to be changed. Mass spectrum: 540.2(M + H).

Synthesis of Compound A5-4:

referring to the synthetic process and the post-treatment purification method of the compound A1-5, only the corresponding raw materials need to be changed. Mass spectrum: 490.4(M + H).

Synthesis of compound a 5:

referring to the synthesis process and the post-treatment purification method of the compound A1, only the corresponding raw materials need to be changed. Mass spectrum: 537.4(M + H).

Synthesis of Compound CPD60

Synthesis of Compound CPD 60-1:

the synthesis process and the post-treatment purification method of the reference compound CPD1-4 only need to change the corresponding raw materials. Mass spectrum: 783.0(M + H).

Synthesis of Compound CPD 60-2:

the synthesis process and the post-treatment purification method of the reference compound CPD1-5 only need to change the corresponding raw materials. Mass spectrum: 769.0(M + H).

Synthesis of compound CPD 60:

referring to the synthesis process and the post-treatment purification method of the compound CPD1, only the corresponding raw materials need to be changed, and the orange compound CPD60(3.95g, yield 55.7%) is obtained. Sublimation purification of 3.95g crude CPD60 gave sublimation pure CPD60(2.27g, 57.4% yield). Mass spectrum: 962.0(M + H).¹HNMR(400MHz,CDCl₃)δ8.65(m,1H),8.20(s,2H),7.96(m,J＝20.0Hz,2H),7.84(m,4H),7.80–7.46(m,11H),7.32(m J＝32.5,22.5Hz,4H),6.97(m,1H),1.32(s,18H).

EXAMPLE 9 Synthesis of Compound CPD85

Synthesis of intermediate A6

Synthesis of Compound A6-2:

referring to the synthetic process and the post-treatment purification method of the compound A1-5, only the corresponding raw materials need to be changed. Mass spectrum: 515.4(M + H).

Synthesis of compound a 6:

referring to the synthesis process and the post-treatment purification method of the compound A1, only the corresponding raw materials need to be changed. Mass spectrum: 562.5(M + H).

Synthesis of Compound CPD85

Synthesis of Compound CPD 85-1:

the synthesis process and the post-treatment purification method of the reference compound CPD1-4 only need to change the corresponding raw materials. Mass spectrum: 808.0(M + H).

Synthesis of Compound CPD 85-2:

the synthesis process and the post-treatment purification method of the reference compound CPD1-5 only need to change the corresponding raw materials. Mass spectrum: 793.0(M + H).

Synthesis of compound CPD 85:

referring to the synthesis process and the post-treatment purification method of the compound CPD1, only the corresponding raw materials need to be changed, and the orange compound CPD85(4.02g, yield 57.3%) is obtained. Sublimation purification of 4.02g crude CPD85 gave sublimation pure CPD85(2.65g, 65.9% yield). Mass spectrum: 987.1(M + H).¹HNMR(400MHz,CDCl₃)δ8.65(m,1H),8.51(m,J＝35.0Hz,2H),8.26(dd,1H),8.20(s,2H),7.84(m,J＝25.0Hz,2H),7.71(t,J＝15.0Hz,3H),7.65–7.37(m,9H),7.36–7.05(m,5H),6.97(m,2H),6.86(m,1H),1.32(s,18H).

EXAMPLE 10 Synthesis of Compound CPD110

Synthesis of Compound CPD110

Synthesis of Compound CPD 110-2:

the synthesis process and the post-treatment purification method of the reference compound CPD1-3 only need to change the corresponding raw materials. Mass spectrum: 499.1(M + H).

Synthesis of Compound CPD 110-3:

the synthesis process and the post-treatment purification method of the reference compound CPD1-4 only need to change the corresponding raw materials. Mass spectrum: 823.0(M + H).

Synthesis of Compound CPD 110-4:

the synthesis process and the post-treatment purification method of the reference compound CPD1-5 only need to change the corresponding raw materials. Mass spectrum: 808.0(M + H).

Synthesis of compound CPD 110:

referring to the synthesis process and the post-treatment purification method of the compound CPD1, only the corresponding raw materials need to be changed to obtain the orange compound CPD110(3.88g, yield 57.1%). Sublimation purification of 3.88g of crude CPD110 yielded sublimed pure CPD110(2.2g, 56.7% yield). Mass spectrum: 1002.1(M + H).¹HNMR(400MHz,CDCl₃)δ8.75(dd,1H),8.48(dd,1H),8.20(s,2H),7.95(m,J＝30.0Hz,2H),7.81(m,J＝30.0Hz,3H),7.73(d,2H),7.62–7.45(m,7H),7.44–7.12(m,7H),6.86(s,1H),2.50(s,3H),1.32(s,18H).

Application example: fabrication of organic electroluminescent devices

50mm 1.0mm glass substrate with ITO (100nm) transparent electrode was ultrasonically cleaned in ethanol for 10 minutes, dried at 150 ℃ and then subjected to N2 Plasma treatment for 30 minutes. The washed glass substrate was mounted on a substrate holder of a vacuum evaporation apparatus, and first, a compound HATCN was evaporated on the surface on the side of the transparent electrode line so as to cover the transparent electrode, thereby forming a thin film with a thickness of 5nm, then, a HTM1 was evaporated, thereby forming a thin film with a thickness of 60nm, and then, a HTM2 was evaporated on the HTM1 thin film, thereby forming a thin film with a thickness of 10nm, and then, a host material 1, a host material 2, and a dopant compound (comparative compound X, CPD X) were evaporated on the HTM2 thin film in a co-evaporation mode, thereby forming a glass substrate with a thickness of 30nm and a ratio of the host material to the dopant material of 45%: 45%: 10 percent. And sequentially evaporating an ETL (25nm) LiQ (1nm) film layer on the light-emitting layer, and finally evaporating a metal Al (100nm) layer as an electrode.

Evaluation:

the above devices were subjected to device performance tests, and in each of examples and comparative examples, the emission spectrum was measured using a constant current power source (Keithley2400), a fixed current density was applied to the light emitting element, and a spectroradiometer (CS 2000). The voltage value and the time for which the test luminance was 90% of the initial luminance were measured at the same time (LT 90). The results are as follows:

as can be seen from the comparison of the data in the above table, the organic electroluminescent device using the compound of the present invention as a dopant exhibited more excellent performance in terms of driving voltage, luminous efficiency, and device lifetime than the comparative compound.

The results show that the compound has the advantages of high light and electrochemical stability, high color saturation, high luminous efficiency, long service life of devices and the like, and can be used in organic electroluminescent devices. In particular, the material can be used as a red emitting dopant, a yellow emitting dopant, or a green emitting dopant, and can be applied to the OLED industry.