Synthesis method for blue light-emitting molecular material

Abstract

Provided in the present invention is a synthesis method for a novel blue light-emitting molecular material, specifically relating to a synthesis method for 2,7,11-tri-tert-butyl-9-(4-(tert-butyl)phenyl)-5-(3',5,5'-tri-tert-butyl-[1,1'-biphenyl]-2-yl)-5H,9H-14-sulfur-5,9-diaza-14b-boronfluorene[3,2,1-de]anthracene. The method can produce a blue light-emitting material having such a substituent structure.

Description

A method for synthesizing blue luminescent molecular material

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to Chinese patent application No. CN202311563508.8 filed on November 22, 2023. The full text of the above-mentioned Chinese patent application is hereby cited as part of this application. Technical Field

[0003] The present invention relates to the technical field of organic electroluminescent materials, and in particular to a method for synthesizing a blue light-emitting molecular material, and in particular to a method for synthesizing 2,7,11-tri-tert-butyl-9-(4-(tert-butyl)phenyl)-5-(3',5,5'-tri-tert-butyl-[1,1'-biphenyl]-2-yl)-5H,9H-14-thio-5,9-diaza-14b-boranofluoren[3,2,1-de]anthracene. Background Art

[0004] In organic light-emitting diodes (OLEDs), stacked devices have higher efficiency and lifespan than single-layer devices and have greater application prospects, so the development of stacked devices has received increasing attention from the industry in recent years. Stacked devices have two or more light-emitting layers, and the two light-emitting layers are connected by a CGL layer (charge generation layer). The currently commonly used CGL layer is usually formed by doping metal lithium or metal ytterbium (Yb) in an electron transport material (ETL). However, due to the strong metallic activity of Li and the strong diffusion ability of Li ions, the ETL material not only needs to have good electron injection and transport capabilities, but also needs to have a certain Li ion binding ability to prevent Li ions from diffusing into adjacent functional layers and affecting the performance of the device. Currently, conventional ETLs can play the role of CGL, but lack the ability to bind Li ions and cannot meet the performance requirements of the CGL layer.

[0005] A new blue luminescent molecular material (D1) plays a positive role in the preparation of organic electroluminescent devices (CN 115850274 A). It is co-deposited with compound H1 on the second hole transport layer to form a 20nm organic film layer to obtain the second light-emitting unit:

[0006] CN 113454093 A discloses a method for synthesizing a structure similar to D1. The structure in CN 113454093 A has completely different substituents from D1. However, the difference in substituents affects the progress of related reactions. For D1, a better synthesis method needs to be developed to meet the needs of the field of organic electroluminescent materials.

[0007] Summary of the Invention

[0008] To address the above technical issues, the present invention provides a synthesis process for a novel blue light-emitting molecular material. Specifically, the present invention uses 2-bromo-4-tert-butylaniline as the starting material and synthesizes Compound 10: 2,7,11-tri-tert-butyl-9-(4-(tert-butyl)phenyl)-5-(3',5,5'-tri-tert-butyl-[1,1'-biphenyl]-2-yl)-5H,9H-14-thio-5,9-diaza-14b-boranofluoren[3,2,1-de]anthracene through a five-step reaction. This material is deposited on a hole transport layer along with other materials to form an organic film layer, thereby obtaining a light-emitting unit. This method offers a more optimal reaction process.

[0009] Specifically, the present invention provides a method for synthesizing 2,7,11-tri-tert-butyl-9-(4-(tert-butyl)phenyl)-5-(3',5,5'-tri-tert-butyl-[1,1'-biphenyl]-2-yl)-5H,9H-14-thio-5,9-diaza-14b-boranofluoren[3,2,1-de]anthracene, comprising:

[0010] a) reacting compound 5 with compound 6 to obtain compound 7;

[0011] b) reacting compound 7 with compound 8 to obtain compound 9;

[0012] c) Compound 9 is subjected to a cyclization reaction to obtain compound 10, namely 2,7,11-tri-tert-butyl-9-(4-(tert-butyl)phenyl)-5-(3',5,5'-tri-tert-butyl-[1,1'-biphenyl]-2-yl)-5H,9H-14-thio-5,9-diaza-14b-boranofluoren[3,2,1-de]anthracene.

[0013] In some embodiments, the method further comprises a method for synthesizing 3',5,5'-tri-tert-butyl-N-(4-(tert-butyl)phenyl)-[1,1'-biphenyl]-2-amine (5),

[0014] Compound 1 is used as the starting material and reacted with compound 2 to obtain compound 3 through coupling reaction; compound 3 is reacted with compound 4 to obtain compound 5, namely 3',5,5'-tri-tert-butyl-N-(4-(tert-butyl)phenyl)-[1,1'-biphenyl]-2-amine.

[0015] In some embodiments, compound 5 and compound 6 react in a first solvent at 100-150°C under the action of a first catalyst and a first base to obtain compound 7; wherein the first catalyst is selected from a palladium catalyst or a palladium catalyst and a ligand; the first base is selected from one or more of sodium tert-butoxide, potassium tert-butoxide and cesium carbonate; the first solvent is selected from one or more of toluene, xylene, DMF, DMAc, NMP and DMSO; preferably, the palladium catalyst is selected from one or more of palladium acetate and Pd2dba3; the ligand is selected from one or more of tri-tert-butylphosphine tetrafluoroborate and tricyclohexylphosphine tetrafluoroborate.

[0016] In some embodiments, the molar ratio of compound 5 to the palladium catalyst in the first catalyst is 1:(0.01-0.04); preferably 1:0.03.

[0017] In some embodiments, the molar ratio of the palladium catalyst to the ligand in the first catalyst is 1:(2-5); preferably 1:2.

[0018] In some embodiments, the molar ratio of compound 5 to the first base is 1:(1.5-5); preferably 1:3.

[0019] In some embodiments, the molar ratio of compound 5 to compound 6 is 1:(1.1-5); preferably, the molar ratio of compound 5 to compound 6 is 1:(1.1-1.5).

[0020] In some embodiments, compound 7 and compound 8 react in a second solvent at 120-160° C. under the action of a second catalyst and a second base to obtain compound 9; wherein the second catalyst is selected from a palladium catalyst, or a palladium catalyst and a ligand; the second base is selected from one or more of sodium tert-butoxide, potassium tert-butoxide and cesium carbonate; the second solvent is selected from one or more of toluene, xylene, DMF, DMAc, NMP and DMSO; preferably, the palladium catalyst is selected from one or more of palladium acetate and Pd2dba3; the ligand is selected from one or more of tri-tert-butylphosphine tetrafluoroborate and tricyclohexylphosphine tetrafluoroborate.

[0021] In some embodiments, the molar ratio of compound 7 to the palladium catalyst in the second catalyst is 1:(0.01-0.04); preferably 1:0.03.

[0022] In some embodiments, the molar ratio of the palladium catalyst to the ligand in the second catalyst is 1:(2-5); preferably 1:2.

[0023] In some embodiments, in some embodiments, the molar ratio of compound 7 to the second base is 1:(2-5); preferably 1:3.

[0024] In some embodiments, the molar ratio of compound 7 to compound 8 is 1:(1.1-5); preferably, the molar ratio of compound 7 to compound 8 is 1:(1.1-1.5).

[0025] In some embodiments, compound 9 is reacted with boron tribromide in a third solvent at 100-150° C. in the presence of a third base and DIEA to obtain compound 10; wherein the third solvent is tert-butylbenzene; and the third base is tert-butyllithium or n-butyllithium.

[0026] In some embodiments, the molar ratio of compound 9 to boron tribromide is 1:(3-6); preferably, the molar ratio of compound 9 to boron tribromide is 1:(3.5-4).

[0027] In some embodiments, the molar ratio of compound 9 to the third base is 1:(2-5); preferably 1:2.5.

[0028] In some embodiments, the molar ratio of compound 9 to DIEA is 1:(3-5); preferably 1:4.

[0029] In some embodiments, compound 1 is reacted with compound 2 in a fourth solvent at 100-150°C under the action of a fourth base and a fourth catalyst to obtain compound 3; wherein the fourth solvent is selected from one or more of toluene and xylene; the fourth base is selected from one or more of potassium carbonate, cesium carbonate and sodium carbonate; the fourth catalyst is selected from one or more of Pd132, Pd(PPh3)4, and Pd(PPh3)2Cl2.

[0030] In some embodiments, the molar ratio of Compound 1 to Compound 2 is 1:(1.1-5); preferably 1:1.2.

[0031] In some embodiments, the molar ratio of compound 1 to the fourth catalyst is 1:(0.005-0.02), preferably 1:0.005.

[0032] In some embodiments, the molar ratio of compound 1 to the fourth base is 1:(1.5-3); preferably 1:2.

[0033] In some embodiments, compound 3 and compound 4 are coupled in a fifth solvent at 100-150°C under the action of a fifth base and a fifth catalyst to obtain compound 5; wherein the fifth solvent is selected from one or more of toluene and xylene; the fifth base is selected from one or more of sodium tert-butoxide and potassium tert-butoxide; the fifth catalyst is palladium acetate and tri-tert-butylphosphine tetrafluoroborate, or palladium acetate and tricyclohexylphosphine tetrafluoroborate.

[0034] In some embodiments, the molar ratio of palladium acetate to tri-tert-butylphosphine tetrafluoroborate, or palladium acetate to tricyclohexylphosphine tetrafluoroborate in the fifth catalyst is 1:2.

[0035] In some embodiments, the molar ratio of compound 3 to compound 4 is 1:(0.9-1.1); preferably 1:1.

[0036] In some embodiments, the molar ratio of compound 3 to the fifth catalyst is 1:(0.005-0.02), preferably 1:0.01.

[0037] In some embodiments, the molar ratio of compound 3 to the fifth base is 1:(1.5-3); preferably 1:2. Beneficial effects

[0038] Compared to existing technologies, the unique structure described in this invention is difficult to connect with the corresponding substituents using conventional methods under conventional coupling reaction conditions due to steric hindrance and electronic effects. Based on the special requirements of the structure, the present invention adjusts the connection sequence and reaction type to enable smooth connection of the relevant groups of compound 5. Using the method described in this invention, the novel blue luminescent molecular material described in this invention is ultimately obtained.

[0039] Terminology

[0040] Certain embodiments of the present invention are now described in detail, examples of which are illustrated by the accompanying structural formulas and chemical formulae. The present invention is intended to encompass all substitutions, modifications, and equivalent technical solutions, which are all included within the scope of the invention as defined in the claims. Those skilled in the art will recognize that many methods and materials similar or equivalent to those described herein can be used to practice the present invention. The present invention is in no way limited to the methods and materials described herein. In the event that one or more of the combined documents, patents, and similar materials differ from or contradict the present application (including but not limited to defined terms, term applications, described technologies, etc.), the present application shall prevail.

[0041] It will be further appreciated that certain features of the invention, which, for clarity, are described in the context of separate embodiments, may also be provided in combination in a single embodiment. Conversely, various features of the invention, which, for brevity, are described in the context of a single embodiment, may also be provided separately or in any suitable subcombination.

[0042] Unless otherwise specified, all technical terms used in the present invention have the same meaning as commonly understood by those skilled in the art to which the present invention belongs. All patents and publications related to the present invention are incorporated herein by reference in their entirety.

[0043] In the description of this specification, the reference terms "one embodiment", "some embodiments", "example", "specific example", or "some examples" mean that the specific features, structures, materials or characteristics described in conjunction with the embodiment or example are included in at least one embodiment or example of the present invention. In this specification, the schematic representations of the above terms do not necessarily refer to the same embodiment or example. Moreover, the specific features, structures, materials or characteristics described can be combined in any one or more embodiments or examples in a suitable manner. In addition, those skilled in the art can combine and combine different embodiments or examples described in this specification and features of different embodiments or examples without contradiction.

[0044] In the following disclosure, all numerical values ​​disclosed herein are approximate, regardless of whether the word "about" or "approximately" is used. The numerical value of each number may vary by 1%, 2%, 5%, 7%, 8%, 10%, 15%, or 20%. Whenever a number having a value of N is disclosed, any number having a value of N+ / -1%, N+ / -2%, N+ / -3%, N+ / -5%, N+ / -7%, N+ / -8%, N+ / -10%, N+ / -15%, or N+ / -20% is expressly disclosed, where "+ / -" means plus or minus. DETAILED DESCRIPTION

[0045] To make the objectives, technical solutions, and advantages of the present invention more clearly understood, the present invention will be further described in detail below with reference to the following examples. The specific embodiments described herein are intended only to illustrate the present invention and are not intended to limit the present invention in any way. In addition, in the following description, descriptions of known structures and technologies are omitted to avoid unnecessary confusion about the concepts of the present disclosure. Such structures and technologies are also described in many publications.

[0046] The reagents used in the present invention can be purchased from the market or prepared by the method described in the present invention.

[0047] Process route:

[0048] Example 1: Synthesis of Compound 3

[0049] In a three-necked flask, compound 1 (100 g, 0.44 mol) was weighed and added, dissolved in toluene (1 L), compound 2 (134 g, 0.53 mol) was weighed, and then ethanol (250 mL) and water (250 mL) were added as solvents. Potassium carbonate (121 g, 0.88 mol) was weighed and replaced with nitrogen three times. Under nitrogen protection, catalyst Pd132 (dichlorodi-tert-butyl-(4-dimethylaminophenyl)phosphine palladium (II), 1.56 g, 2.20 mmol) was weighed and added to the reaction system, heated to 120 ° C for 8 hours. TLC monitored the completion of the reaction. The product was diluted with ethyl acetate (1000 mL), and water (500 mL) was added to separate the organic phase. The solvent was spin-dried, hydrochloric acid (200 mL) was added and stirred thoroughly to form a salt, and the mixture was slurried and filtered with ethyl acetate (400 mL) to obtain compound 3 as a light gray solid powder (120 g, yield 81%, purity 99%).

[0050] 1 H NMR(400MHz,Chloroform-d)δ7.43(q,J=1.8Hz,1H),7.32(t,J=1.9Hz,2H),7.21(dd,J=7.1,2.1 Hz, 2H), 6.75 (dd, J = 8.8, 1.8 Hz, 1H), 3.69 (s, 2H), 1.38 (d, J = 2.0 Hz, 18H), 1.33 (d, J = 2.0 Hz, 9H).

[0051] Example 2: Synthesis of Compound 5

[0052] Compound 3 (100 g, 0.30 mol) was weighed into a three-necked flask, and toluene (1000 ml) was added. Compound 4 (80.91 g, 0.31 mol) was weighed and sodium tert-butoxide (56.9 g, 0.59 mol) was added. The atmosphere was purged with nitrogen three times. Under nitrogen protection, the catalyst palladium acetate (0.67 g, 3.0 mmol) and the ligand tri-tert-butylphosphine tetrafluoroborate (1.8 g, 6.0 mmol) were added. The temperature was raised to 115°C and the reaction was allowed to react for 8 hours. TLC monitoring confirmed the completion of the reaction. Post-treatment: Ethyl acetate (1500 mL) and water (500 mL) were added for separation to obtain an organic phase, which was directly spin-dried to obtain a crude solid. The crude product was slurried with (petroleum ether:ethyl acetate = 10:1) to obtain compound 5 as a white solid (130 g, yield 93%, purity 95%).

[0053] 1H NMR(400MHz,Chloroform-d)δ7.63(d,J=8.3Hz,1H),7.44(s,1H),7.35(s,1H),7.29(d,J=3.8Hz,2H), 7.22(s,3H),7.02(d,J=8.0Hz,2H),1.38(d,J=2.9Hz,9H),1.33(d,J=2.8Hz,18H),1.31-1.27(m,9H).

[0054] Example 3: Synthesis of Compound 7

[0055] Compound 5 (120 g, 0.25 mol) was weighed into a three-necked flask, and toluene (1200 ml) was added, followed by compound 6 (86.4 g, 0.31 mol) and sodium tert-butoxide (73.6 g, 0.77 mol). The atmosphere was purged with nitrogen three times. Under nitrogen protection, the catalyst, palladium acetate (1.7 g, 7.70 mmol), and the ligand, tri-tert-butylphosphine tetrafluoroborate (5.3 g, 15.40 mmol), were added. The temperature was raised to 110°C and the reaction was allowed to proceed overnight. TLC analysis indicated a small amount of residual starting material. Ethyl acetate (1500 ml) and water (500 ml) were added for post-processing, and the mixture was separated by stirring. The organic phase was then dried and purified by column chromatography using a mixture of petroleum ether:ethyl acetate (50:1) to afford compound 7 as a white solid (60 g, 42% yield, 97% purity).

[0056] 1 H NMR(400MHz,Chloroform-d)δ8.04(d,J=8.7Hz,1H),7.89(d,J=8.9Hz,2H),7.82(s,1H),7.76(d,J=8.5Hz,3H),7.63(s,2H) ,7.28(s,1H),7.08(d,J=8.3Hz,2H),1.94(d,J=1.9Hz,9H),1.82(s,7H),1.77(p,J=3.9,1.9Hz,18H),1.67(d,J=1.9Hz,9H).

[0057] Example 4: Synthesis of Compound 9

[0058] Compound 7 (60 g, 0.10 mol) was weighed into a three-necked flask, and xylene (600 mL) was added. Compound 8 (40 g, 0.12 mol) was then weighed, and sodium tert-butoxide (28.1 g, 0.29 mol) was added. The atmosphere was replaced with nitrogen three times. Under nitrogen protection, the catalyst palladium acetate (0.66 g, 2.93 mmol) and the ligand tri-tert-butylphosphine tetrafluoroborate (1.70 g, 5.86 mmol) were added to the system. The temperature was raised to 140°C and the reaction was allowed to proceed overnight. TLC monitoring showed that the raw material reaction was basically complete. After post-treatment, ethyl acetate (1500 mL) was added and water (500 mL) was added for separation. The organic phase was spin-dried, mixed, and passed through a column. The product was rinsed out with PE to obtain compound 9 (30 g, yield 32%, purity 95%).

[0059] 1 H NMR(400MHz,Chloroform-d)δ7.98(s,1H),7.73(d,J=8.4Hz,1H),7.68(d,J=8.5Hz,1H ),7.40(dd,J=8.4,4.8Hz,2H),7.35(d,J=2.2Hz,1H),7.32-7.27(m,3H),7.22(s,1H), 7.15(d,J=8.3Hz,2H),7.08(d,J=8.5Hz,1H),7.03-6.96(m,3H),6.44(d,J=7.5Hz,3H) ,6.37(d,J=2.1Hz,1H),1.38(s,9H),1.29(s,9H),1.23(d,J=5.1Hz,27H),1.19(s,9H).

[0060] Example 5: Synthesis of Compound 10

[0061] Compound 9 (15 g, 0.015 mol) was weighed into a three-necked flask, tert-butylbenzene (150 mL) was added, nitrogen was replaced 4 times, the system was cooled to about 0°C in an ice bath, tert-butyllithium (30 mL, 0.038 mol) was slowly added dropwise, after the addition was complete, the mixture was stirred at 0°C for 10 min, then returned to room temperature to 25°C and stirred for 2 h, the reaction system was cooled to -30°C again, boron tribromide (13.5 g, 0.054 mol) was slowly added dropwise into the system, after the addition was complete, the mixture was returned to room temperature and reacted for 30 min, then the system was cooled to 0°C, DIEA (7.8 g, 0.06 mol) was slowly added dropwise, after the addition was complete, the system was heated to 120°C and reacted for 8 h, TLC monitoring showed that the reaction was complete. Petroleum ether (200 mL) was added to precipitate some yellow solid powder, which was then mixed and passed through a column with dichloromethane:petroleum ether = 15:1 to obtain the product, compound 10, a bright yellow solid powder (1.5 g, yield 16%, purity 99.3%).

[0062] 1 H NMR (400MHz, Chloroform-d) δ7.77 (d, J = 2.1Hz, 1H), 7.76-7.73 (m, 2H), 7.73-7.66 (m, 1H), 7.63-7. 59(m,1H),7.50-7.45(m,1H),7.36-7.30(m,1H),7.30-7.26(m,2H),7.15-7.10(m,3H),7.05(t,J=1. 8Hz,1H),6.92(d,J=1.8Hz,2H),6.91(d,J=2.4Hz,1H),6.85(d,J=8.9Hz,1H),6.37-6.34(m,1H),6. 31(d,J=1.8Hz,1H),1.55(s,9H),1.53(s,9H),1.29(s,9H),1.12(s,9H),1.04(s,9H),0.96(s,18H).

[0063] Comparative Example:

[0064] Compound 10 was synthesized using compound 6 as the starting material:

[0065] Synthesis of compound 9-a

[0066] Compound 6 (10 g, 0.03 mol) was weighed into a three-necked flask, and xylene (600 mL) was added. Compound 8 (9.97 g, 0.04 mol) was then weighed, and sodium tert-butoxide (5.66 g, 0.06 mol) was added. The atmosphere was replaced with nitrogen three times. Under nitrogen protection, the catalyst palladium acetate (0.06 g, 0.29 mmol) and the ligand tri-tert-butylphosphine tetrafluoroborate (0.17 g, 0.58 mmol) were added to the system, and the temperature was raised to 140°C and reacted overnight. TLC monitoring showed that the raw material reaction was basically completed. After post-treatment, ethyl acetate (100 mL) and water (50 mL) were added for separation. The organic phase was spin-dried, mixed, and passed through a column. The product was flushed out with PE to obtain compound 9-a (10 g, yield 64%, purity 92%).

[0067] 1H NMR(400MHz,Chloroform-d)δ7.78(d,J=8.6Hz,1H),7.59(d,J=2.0Hz,1H),7.49(dd,J=8.6,1.9Hz,1H),7.42(d,J=2.2Hz,1H),7.3 1-7.24(m,2H),7.15-7.09(m,2H),6.65(dd,J=8.6,1.8Hz,2H),1.32(d,J=2.0Hz,9H),1.26(d,J=1.7Hz,9H),1.18(d,J=1.7Hz,9H).

[0068] Synthesis of compound 9

[0069] Compound 9-a (5 g, 9.25 mmol) was weighed into a three-necked flask, and xylene (600 mL) was added. Compound 5 (5.62 g, 11.10 mmol) was then weighed, and sodium tert-butoxide (1.77 g, 18 mmol) was added. The atmosphere was purged with nitrogen three times. Under nitrogen protection, the catalyst, palladium acetate (2.0 mg, 0.09 mmol), and the ligand, tri-tert-butylphosphine tetrafluoroborate (5.0 mg, 0.19 mmol), were added to the system. The temperature was raised to 140°C and the reaction was allowed to proceed overnight. TLC monitoring showed no reduction in the starting material, indicating no reaction.

[0070] The reaction conditions were screened, and the results are shown in Table 1:

[0071] Table 1

[0072] As can be seen from the reaction results shown in Table 1, for the structure involved in the present invention, if compound 8 is first connected, compound 5 is difficult to connect to the parent core under conventional coupling reaction conditions due to steric hindrance and electronic effects. Based on the special requirements of the structure, the present invention creatively proposes to adjust the connection order and reaction type so that the related groups of compound 5 can be smoothly connected. Using the method described in the present invention, the new blue light-emitting molecular material described in the present invention is finally obtained.

[0073] The methods of the present invention have been described through preferred embodiments. It is apparent that those skilled in the art will be able to modify or appropriately alter and combine the methods and applications described herein within the scope, spirit, and spirit of the present invention to implement and apply the technology of the present invention. Those skilled in the art may refer to the disclosure herein and appropriately modify the process parameters to achieve the desired effect. It is particularly important to note that all similar substitutions and modifications apparent to those skilled in the art are considered encompassed by the present invention.

Claims

1. Synthesis method of 2,7,11-tritert-butyl-9-(4-(tert-butyl)phenyl)-5-(3',5,5'-tritert-butyl-[1,1'-biphenyl]-2-yl)-5H,9H-14-sulfur-5,9-diaza-14b-borafluorene[3,2,1-de]anthracene including: d) Reacting compound 5 with compound 6 to obtain compound 7; e) Reacting compound 7 with compound 8 to obtain compound 9; f) Obtaining compound 10, namely 2,7,11-tritert-butyl-9-(4-(tert-butyl)phenyl)-5-(3',5,5'-tritert-butyl-[1,1'-biphenyl]-2-yl)-5H,9H-14-sulfur-5,9-diaza-14b-borafluorene[3,2,1-de]anthracene, by cyclization reaction of compound 9.

2. The method according to claim 1, characterized in that, Also included is a method for synthesizing 3',5,5'-tri-tert-butyl-N-(4-(tert-butyl)phenyl)-[1,1'-biphenyl]-2-amine (5). using compound 1 as the starting material, coupling reaction with compound 2 to obtain compound 3; coupling reaction of compound 3 with compound 4 to obtain compound 5, namely 3',5,5'-tritert-butyl-N-(4-(tert-butyl)phenyl)-[1,1'-biphenyl]-2-amine.

3. The method according to claim 1 or 2, characterized in that, Compound 5 and compound 6 react in a first solvent at 100-150° C. under the action of a first catalyst and a first base to obtain compound 7; wherein the first catalyst is selected from a palladium catalyst or a palladium catalyst and a ligand; the first base is selected from one or more of sodium tert-butoxide, potassium tert-butoxide and cesium carbonate; the first solvent is selected from one or more of toluene, xylene, DMF, DMAc, NMP and DMSO; preferably, the palladium catalyst is selected from palladium acetate and Pd 2 dba 3 One or more of; the ligand is selected from one or more of tri-tert-butylphosphine tetrafluoroborate and tricyclohexylphosphine tetrafluoroborate.

4. The method according to claim 1 or 2, characterized in that, the molar ratio of compound 5 to compound 6 is 1:(1.1 - 5); preferably, the molar ratio of compound 5 to compound 6 is 1:(1.1 - 1.5).

5. The method according to claim 1 or 2, characterized in that, Compound 7 and compound 8 react in a second solvent at 120-160° C. under the action of a second catalyst and a second base to obtain compound 9; wherein the second catalyst is selected from a palladium catalyst or a palladium catalyst and a ligand; the second base is selected from one or more of sodium tert-butoxide, potassium tert-butoxide and cesium carbonate; the second solvent is selected from one or more of toluene, xylene, DMF, DMAc, NMP and DMSO; preferably, the palladium catalyst is selected from palladium acetate and Pd 2 dba 3 One or more of; the ligand is selected from one or more of tri-tert-butylphosphine tetrafluoroborate and tricyclohexylphosphine tetrafluoroborate.

6. The method according to claim 1 or 2, characterized in that, the molar ratio of compound 7 to compound 8 is 1:(1.1 - 5); preferably, the molar ratio of compound 7 to compound 8 is 1:(1.1 - 1.5).

7. The method according to claim 1 or 2, characterized in that, compound 9 reacts with boron tribromide at 100 - 150 °C under the action of a third base and DIEA in a third solvent to obtain compound 10; wherein, the third solvent is tert-butylbenzene; the third base is tert-butyllithium or n-butyllithium.

8. The method according to claim 1 or 2, characterized in that, the molar ratio of compound 9 to boron tribromide is 1:(3 - 6); preferably, the molar ratio of compound 9 to boron tribromide is 1:(3.5 - 4).

9. The method according to claim 2, characterized in that, Compound 1 reacts with Compound 2 in a fourth solvent under the action of a fourth base and a fourth catalyst at 100-150 °C to obtain Compound 3; wherein, the fourth solvent is selected from one or more of toluene and xylene; the fourth base is selected from one or more of potassium carbonate, cesium carbonate and sodium carbonate; the fourth catalyst is selected from one or more of Pd132, Pd(PPh 3 ) 4 and Pd(PPh 3 ) 2 Cl 2 ; preferably, the molar ratio of Compound 1 to Compound 2 is 1:(1.1-5).

10. The method according to claim 2, characterized in that, compound 3 and compound 4 carry out a coupling reaction at 100 - 150 °C under the action of a fifth base and a fifth catalyst in a fifth solvent to obtain compound 5; wherein, the fifth solvent is selected from one or more of toluene and xylene; the fifth base is selected from one or more of sodium tert-butoxide and potassium tert-butoxide; the fifth catalyst is palladium acetate and tetrabutylphosphonium tetrafluoroborate, or palladium acetate and tricyclohexylphosphonium tetrafluoroborate; preferably, the molar ratio of compound 3 to compound 4 is 1:(0.9 - 1.1).

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