Organic compound and preparation method thereof, and light-emitting device

Abstract

The present invention discloses an organic compound and a preparation method thereof, and a light-emitting device. The organic compound includes a compound with a general structural formula as shown in Formula M: wherein R is an electron-withdrawing group. The present invention introduces a double boron structure into the organic compound, so that the structure has a strong electronegativity, thereby reducing the electron injection barrier. At the same time, the electron-withdrawing group is introduced into the double boron structure, which can not only improve the electronegativity, but also reduce the energy level of the material itself, thereby improving the electron transmission efficiency and stability of the organic compound.

Description

Technical Field

[0001] The present invention relates to the field of display technology, and in particular to an organic compound and a preparation method thereof, and a light-emitting device. Background Art

[0002] Electroluminescent devices include organic light-emitting diodes (OLED) and quantum dot light-emitting diodes (QLED). They have many display characteristics and qualities that surpass liquid crystal displays (LCD), such as low energy consumption and flexibility, and have good application prospects, and will become the next generation of mainstream flat-panel displays.

[0003] In electroluminescent devices, electrons and holes transmitted from both sides converge in the light-emitting layer to form excitons, and emit light through the recombination of excitons. The electron transport material plays an important role in this. Electron transport materials with excellent performance can greatly reduce the electron injection barrier, reduce the voltage of the device, and improve the efficiency of the device. At present, there is a lack of efficient and stable electron transport materials, which restricts the performance of electroluminescent devices, resulting in low device efficiency. Summary of the invention

[0004] The embodiments of the present invention provide an organic compound and a preparation method thereof, and a light-emitting device, which can solve the technical problem that the light-emitting efficiency of the device is affected due to the lack of efficient and stable electron transport materials.

[0005] In order to solve the above technical problems, an embodiment of the present invention provides an organic compound, wherein the organic compound includes a compound having a general structural formula as shown in Formula M:

[0006] Wherein, R is an electron withdrawing group.

[0007] In one embodiment of the present invention, each R is independently selected from a substituted or unsubstituted pyridine group, a substituted or unsubstituted quinoline group, a substituted or unsubstituted quinoxaline group, a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted pyrazole group, a substituted or unsubstituted oxazole group, a substituted or unsubstituted triazine group, a substituted or unsubstituted phosphine group, a substituted or unsubstituted pyrimidine group, or a combination of these systems.

[0008] In one embodiment of the present invention, each of the Rs is independently selected from any one of the following:

[0009]

[0010]

[0011] In one embodiment of the present invention, the organic compound is any one of the structures shown in the following M1 to M21:

[0012]

[0013]

[0014]

[0015] According to the above object of the present invention, there is provided a method for preparing an organic compound, comprising the following steps:

[0016] Under a protective gas atmosphere, the halide containing R undergoes a first reaction with the intermediate compound to obtain the organic compound;

[0017] The structural formula of the halide containing R is R-X1, and the structural formula of the intermediate compound is Wherein, X1 and X2 are both halogen atoms;

[0018] The organic compound includes a compound with a general structural formula as shown in Formula M:

[0019] Wherein, the R is an electron-withdrawing group.

[0020] In one embodiment of the present invention, the method for preparing the halide containing R comprises:

[0021] A halide containing R1 undergoes a coupling reaction with a borate containing an aryl group, and the aryl group contains the X1, wherein the R1 is combined with the aryl group to obtain the halide containing R; and

[0022] The preparation method of the intermediate compound comprises:

[0023] The ortho-disubstituted benzene ring structure reacts with a boron halide to obtain the intermediate compound;

[0024] Wherein, the R1 is an electron-withdrawing fused ring unit, and the structural formula of the ortho-disubstituted benzene ring structure is The boron halide has a structural formula of B-(X2)3, and R2 is a silicon-based structure containing an alkyl group.

[0025] In one embodiment of the present invention, the first reaction comprises:

[0026] Under a protective gas atmosphere, dissolving the halide containing R in a solvent to form a first solution;

[0027] adding an alkaline agent to the first solution at a first temperature, and reacting at a second temperature to obtain a second solution; and

[0028] The intermediate compound is added to the second solution at a first temperature, and reacted at a third temperature to obtain the compound.

[0029] In one embodiment of the present invention, the second temperature is higher than the first temperature, and the third temperature is higher than the second temperature.

[0030] In one embodiment of the present invention, the first temperature is -80°C to -70°C, the second temperature is -40°C to -20°C, and the third temperature is 20°C to 30°C.

[0031] According to the above-mentioned purpose of the present invention, a light-emitting device is provided, which includes a first electrode, a second electrode and a light-emitting layer arranged between the first electrode and the second electrode, and the light-emitting layer includes the organic compound, or an organic compound prepared by the preparation method of the organic compound.

[0032] According to the above-mentioned purpose of the present invention, a light-emitting device is provided, which includes a first electrode, a second electrode, and a light-emitting layer and an electron transport layer arranged between the first electrode and the second electrode and stacked, and the electron transport layer and / or the light-emitting layer include the organic compound, or an organic compound prepared by the method for preparing the organic compound.

[0033] Beneficial effects of the present invention: The present invention introduces a diboron structure into an organic compound. Since the boron atom itself has a vacant p-orbital, the structure has a strong electronegativity, thereby reducing the electron injection barrier. At the same time, the introduction of an electron-withdrawing group into the diboron structure can increase the electronegativity and reduce the energy level, thereby playing a role in blocking holes. The separation of the plane where the diboron structure and the benzene ring are connected and the planar structure of the electron-withdrawing group can achieve the widening of the band gap of the organic compound itself and the improvement of the triplet energy level, thereby improving the electron transmission efficiency and stability of the organic compound. BRIEF DESCRIPTION OF THE DRAWINGS

[0034] The technical solutions and other beneficial effects of the present invention will be made apparent by describing in detail the specific embodiments of the present invention in conjunction with the accompanying drawings.

[0035] Figure 1 A flow chart of a method for preparing an organic compound provided by an embodiment of the present invention;

[0036] Figure 2 A schematic structural diagram of a light emitting device provided in an embodiment of the present invention. DETAILED DESCRIPTION

[0037] The technical solutions in the embodiments of the present invention will be described clearly and completely below in conjunction with the accompanying drawings in the embodiments of the present invention. Obviously, the described embodiments are only part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present invention.

[0038] The disclosure below provides many different embodiments or examples to realize different structures of the present invention. In order to simplify the disclosure of the present invention, the parts and settings of specific examples are described below. Of course, they are only examples, and the purpose is not to limit the present invention. In addition, the present invention can repeat reference numbers and / or reference letters in different examples, and this repetition is for the purpose of simplicity and clarity, which itself does not indicate the relationship between the various embodiments and / or settings discussed. In addition, the present invention provides various specific examples of processes and materials, but those of ordinary skill in the art can be aware of the application of other processes and / or the use of other materials.

[0039] The embodiments of the present invention provide an organic compound and a preparation method thereof, and a light-emitting device, which can solve the technical problem that the light-emitting efficiency of the device is affected due to the lack of efficient and stable electron transport materials.

[0040] In order to solve the above technical problems, an embodiment of the present invention provides an organic compound, wherein the organic compound includes a compound having a general structural formula as shown in Formula M:

[0041] Wherein, R is an electron withdrawing group.

[0042] In the implementation and application process, the embodiment of the present invention forms a double boron structure with multiple coordination of boron atoms by introducing two boron atoms and two benzene rings in an organic compound. Since the boron atom itself has a vacant p- orbital, the structure has a strong electronegativity, which can reduce the injection barrier of electrons. At the same time, the electron-withdrawing group is introduced into the double boron structure, which can not only improve the electronegativity, but also reduce the energy level of the material itself, thereby playing a role in blocking holes, and the plane where the structure where the two boron atoms and the benzene rings are connected is separated from the planar structure of the electron-withdrawing group, which can achieve the widening of the band gap of the organic compound itself and the improvement of the triplet energy level. Further, in the embodiment of the present invention, the two boron atoms are directly connected to the two benzene rings and form a ring structure, which improves the molecular rigidity and planarity of the organic compound, and better planarity contributes to the transmission of electrons, and better rigidity improves the stability of the compound, thereby improving the electronic transmission efficiency and stability of the organic compound.

[0043] In an embodiment of the present invention, R is an electron withdrawing group, and can be specifically selected from any one of the following: a substituted or unsubstituted pyridine group, a substituted or unsubstituted quinoline group, a substituted or unsubstituted quinoxaline group, a substituted or unsubstituted benzimidazole group, a substituted or unsubstituted pyrazole group, a substituted or unsubstituted oxazole group, a substituted or unsubstituted triazine group, a substituted or unsubstituted phosphineoxy group, a substituted or unsubstituted pyrimidine group, or a combination of these systems.

[0044] Optionally, R can be any of the following groups, where "*" represents a connection site to other groups:

[0045]

[0046]

[0047] Optionally, the compound represented by formula M is any one of the structures represented by the following structures M1 to M21:

[0048]

[0049]

[0050] It should be noted that the structure of the organic compound provided in the embodiment of the present invention is not limited to the structures shown in the above M1 to M21, and the above structures are only taken as examples for illustration.

[0051] In addition, an embodiment of the present invention further provides a method for preparing an organic compound, the method comprising:

[0052] Under a protective gas atmosphere, the halide containing R undergoes a first reaction with the intermediate compound to obtain an organic compound.

[0053] The structural formula of the halide containing R is R-X1, and the structural formula of the intermediate compound is Wherein, X1 and X2 are both halogen atoms;

[0054] The organic compound includes a compound with a general structural formula as shown in Formula M:

[0055] Wherein, R is an electron withdrawing group.

[0056] For details, please refer to Figure 1 , the preparation method of the organic compound comprises:

[0057] S10. A halide containing R1 undergoes a coupling reaction with a borate containing an aromatic group, and the aromatic group contains X1, wherein R1 is combined with the aromatic group to obtain a halide containing R.

[0058] S20, the o-disubstituted benzene ring structure reacts with a boron halide to obtain an intermediate compound.

[0059] S30. Under a protective gas atmosphere, the halide containing R undergoes a first reaction with the intermediate compound to obtain an organic compound.

[0060] Among them, R1 is an electron-withdrawing fused ring unit, and the structural formula of the ortho-disubstituted benzene ring structure is The structural formula of the boron halide is B-(X2)3, and R2 is a silicon-based structure containing an alkyl group.

[0061] As mentioned above, in the method for preparing an organic compound, step S10 is a process for preparing a halide containing R, and step S20 is a process for preparing an intermediate compound, and the order of step S10 and step S20 is not limited and can be interchanged.

[0062] It should be noted that in the borate ester containing an aromatic group, X1 is located on the aromatic structure, and during the coupling reaction of the halide containing R1 and the borate ester containing an aromatic group, the borate group combines with the halogen atom in the halide containing R1, and R1 combines with the aromatic group to form a halide containing R, i.e., R-X1.

[0063] Optionally, R2 may be a trimethylsilyl group, X1 and X2 may be halogen atoms, and X1 and X2 may be the same or different. Preferably, X1 and X2 may be Br, and the following embodiments are described by taking X1 and X2 as Br as an example.

[0064] In the embodiments of the present invention, the halogen in the halide containing R1, the borate containing an aromatic group, and the halide of boron can be a bromine atom, and the bromide containing R1 and the bromide of boron are used as examples for explanation in the subsequent embodiments. Among them, the bromine atom in the borate containing an aromatic group is located on the aromatic group.

[0065] Optionally, the preparation process of the halide containing R is as follows:

[0066]

[0067] Specifically, during the coupling reaction of the bromide containing R1 and the borate containing an aryl group, the borate group combines with the bromine atom in the bromide containing R1, and R1 combines with the bromine-substituted aryl group to form a halide containing R.

[0068] Among them, the group corresponding to R is R1 may be an electron-withdrawing fused ring unit, and R3 may be a hydrogen atom or an alkyl chain having 1 to 12 carbon atoms.

[0069] Optionally, R3 is a methyl group or a hydrogen atom, and the catalyst in the reaction process includes a palladium catalyst, specifically Pd(PPh3)4.

[0070] Further, the bromide R1-Br containing R1 and the borate containing aromatic group The molar ratio is between 1.5 and 1. Preferably, the bromide R1-Br containing R1 and the borate containing aromatic groups The molar ratio is 6:5.

[0071] Optionally, the boron bromide is boron tribromide, and the structural formula of the ortho-disubstituted benzene ring structure is Wherein the TMS group is trimethylsilyl, the preparation process of the intermediate compound is as follows:

[0072]

[0073] The specific preparation method of the intermediate compound can be referred to the synthesis method in the literature [ACS Appl. Mater. Interfaces 2020, 12, 23199-23206], which will not be repeated here.

[0074] Based on the above, the reaction process of the halide containing R and the intermediate compound is as follows:

[0075]

[0076] Specifically, in the embodiment of the present invention, step S30 in the method for preparing an organic compound, i.e., the first reaction, comprises:

[0077] Under a protective gas atmosphere, a halide containing R is dissolved in a solvent to form a first solution.

[0078] Optionally, the protective gas includes nitrogen, and the solvent includes anhydrous ether solvent.

[0079] An alkaline agent is added to the first solution at a first temperature, and reacted at a second temperature to obtain a second solution.

[0080] Optionally, the alkaline agent comprises tert-butyl lithium.

[0081] The intermediate compound is added to the second solution at the second temperature, and reacted at the third temperature to obtain a compound.

[0082] The second temperature is higher than the first temperature, the third temperature is higher than the second temperature, and the third temperature may be room temperature. Specifically, the first temperature is -80°C to -70°C, the second temperature is -40°C to -20°C, and the third temperature is 20°C to 30°C. In an embodiment of the present invention, the molar ratio of the halide containing R to the intermediate compound is between 3 and 2, and preferably, the molar ratio of the halide containing R to the intermediate compound is 2:1.

[0083] The preparation process of the organic compounds in the embodiments of the present invention will be described in detail below in conjunction with specific embodiments, wherein M1, M9, M12, M17 and M20 are used as examples for illustration. The synthesis of compounds M2, M3, M4, M5, M7, M8, M10, M11, M13, M14, M15, M16, M18, M19 and M21 can be achieved by referring to the following embodiments.

[0084] Example 1, Preparation of Compound M1:

[0085] The structural formula of compound M1 is shown below:

[0086]

[0087] 1.2 mmol of bromide containing R1, 1 mmol of borate containing aromatic group and 0.1 mmol of palladium catalyst are added into the reactor, and the reaction environment is made into a protective gas atmosphere. Specifically, vacuum pumping and nitrogen replacement operation can be repeated three times to make the environment into a protective gas atmosphere.

[0088] The reactor includes a 50 mL two-necked bottle, and the bromide containing R1 is a bromine-substituted pyridine compound. The borate ester containing an aromatic group is The palladium catalyst is Pd(PPh3)4.

[0089] Then, 30 mL of toluene solvent and 3 mL of 2M (mol / L) K2CO3 solution were added to the reactor, and the reaction was carried out at 110°C for 12 h. The reaction solution was then cooled to room temperature, and extracted and separated with dichloromethane solvent. Then, a silica gel column was used for separation and purification, and n-hexane was used as an eluent. The solvent was removed by rotary evaporation to collect the product, and finally vacuum dried at room temperature for 12 h to obtain a halogenated compound containing R. The reaction process is as follows:

[0090]

[0091] In another reactor, 0.5 mmol of a halide containing R is dissolved in anhydrous ether solvent. Similarly, the environment is protected by nitrogen and the temperature is set to -78°C. 0.7 mmol of tert-butyl lithium (t-BuLi) solution is slowly added to the reactor to form a first solution, and the temperature is raised to -30°C for reaction for 1 hour to obtain a second solution. The temperature of the second solution is then lowered to -78°C, and a toluene solution of 0.25 mmol of the intermediate compound is added dropwise to the second solution. After the addition is completed, the second solution is heated to room temperature, specifically 25°C, and reacted for 4 hours. After the reaction is completed, a reaction solution is obtained, and the reaction process is as follows:

[0092]

[0093] 30 mL of saturated ammonium chloride solution was added to the reaction solution, followed by extraction and separation with dichloromethane solvent, separation and purification with silica gel column, using n-hexane / dichloromethane as eluent, rotary evaporation to remove the solvent and collect the product, and finally vacuum drying at room temperature for 12 hours to obtain compound M1. The molecular structure identification data of the product are as follows: 1HNMR (300MHz, DMSO), δ (TMS, ppm): 9.24 (s, 2H), 8.70 (d, 4H), 8.42 (d, 2H), 7.75 (d, 4H), 7.68 (s, 4H), 7.57 (t, 2H), 7.35 (d, 4H), 2.33 (s, 12H), indicating that the product is M1.

[0094] Example 2, Preparation of Compound M9:

[0095] The structural formula of compound M9 is shown below:

[0096]

[0097] 1.2 mmol of bromide containing R1, 1 mmol of borate containing aromatic group and 0.1 mmol of palladium catalyst are added into the reactor, and the reaction environment is made into a protective gas atmosphere. Specifically, vacuum pumping and nitrogen replacement operation can be repeated three times to make the environment into a protective gas atmosphere.

[0098] The reactor includes a 50 mL two-necked bottle containing the bromide of R1. The borate ester containing an aromatic group is The palladium catalyst is Pd(PPh3)4.

[0099] Then, 30 mL of toluene solvent and 3 mL of 2M (mol / L) K2CO3 solution were added to the reactor, and the reaction was carried out at 110°C for 12 h. The reaction solution was then cooled to room temperature, and extracted and separated with dichloromethane solvent. Then, a silica gel column was used for separation and purification, and n-hexane was used as an eluent. The solvent was removed by rotary evaporation to collect the product, and finally vacuum dried at room temperature for 12 h to obtain a halogenated compound containing R. The reaction process is as follows:

[0100]

[0101] In another reactor, 0.5 mmol of a halide containing R is dissolved in anhydrous ether solvent. Similarly, the environment is protected by nitrogen and the temperature is set to -78°C. 0.7 mmol of tert-butyl lithium (t-BuLi) solution is slowly added to the reactor to form a first solution, and the temperature is raised to -30°C for reaction for 1 hour to obtain a second solution. The temperature of the second solution is then lowered to -78°C, and a toluene solution of 0.25 mmol of the intermediate compound is added dropwise to the second solution. After the addition is completed, the second solution is heated to room temperature, specifically 25°C, and reacted for 4 hours. After the reaction is completed, a reaction solution is obtained, and the reaction process is as follows:

[0102]

[0103] 30 mL of saturated ammonium chloride solution was added to the reaction solution, followed by extraction and separation with dichloromethane solvent, separation and purification with silica gel column, using n-hexane / dichloromethane as eluent, rotary evaporation to remove the solvent and collect the product, and finally vacuum drying at room temperature for 12 hours to obtain compound M9. The molecular structure identification data of the product are as follows: 1HNMR (300MHz, DMSO), δ (TMS, ppm): 9.19 (s, 2H), 8.51 (s, 2H), 8.16 (d, 2H), 7.81-7.75 (m, 6H), 7.68 (s, 4H), 7.61 (t, 2H), 7.35-7.31 (m, 6H), 2.33 (s, 12H), indicating that the product is M9.

[0104] Example 3, Preparation of Compound M12:

[0105] The structural formula of compound M12 is shown below:

[0106]

[0107] Take the triazine product containing R as bromide, and the structural formula is as follows:

[0108]

[0109] In a reactor, 0.5 mmol of a halide containing R is dissolved in anhydrous ether solvent. Similarly, the environment is protected by nitrogen and the temperature is set to -78°C. 0.7 mmol of tert-butyl lithium (t-BuLi) solution is slowly added to the reactor to form a first solution, and the temperature is raised to -30°C for reaction for 1 hour to obtain a second solution. The temperature of the second solution is then lowered to -78°C, and a toluene solution of 0.25 mmol of the intermediate compound is added dropwise to the second solution. After the addition is completed, the second solution is heated to room temperature, specifically 25°C, and reacted for 4 hours. After the reaction is completed, a reaction solution is obtained, and the reaction process is as follows:

[0110]

[0111] 30 mL of saturated ammonium chloride solution was added to the reaction solution, followed by extraction and separation with dichloromethane solvent, separation and purification with silica gel column, using n-hexane / dichloromethane as eluent, rotary evaporation to remove the solvent and collect the product, and finally vacuum drying at room temperature for 12 hours to obtain compound M12. The molecular structure identification data of the product are as follows: 1HNMR (300MHz, DMSO), δ (TMS, ppm): 8.36 (d, 8H), 7.94 (d, 4H), 7.77-7.75 (m, 8H), 7.50 (m, 12H), 7.35 (m, 4H), indicating that the product is M12.

[0112] Example 4. Preparation of Compound M17:

[0113] The structural formula of compound M17 is shown below:

[0114]

[0115] 1.2 mmol of bromide containing R1, 1 mmol of borate containing aromatic group and 0.1 mmol of palladium catalyst are added into the reactor, and the reaction environment is made into a protective gas atmosphere. Specifically, vacuum pumping and nitrogen replacement operation can be repeated three times to make the environment into a protective gas atmosphere.

[0116] The reactor includes a 50 mL two-necked bottle containing the bromide of R1. The borate ester containing an aromatic group is The palladium catalyst is Pd(PPh3)4.

[0117] Then, 30 mL of toluene solvent and 3 mL of 2M (mol / L) K2CO3 solution were added to the reactor, and the reaction was carried out at 110°C for 12 h. The reaction solution was then cooled to room temperature, and extracted and separated with dichloromethane solvent. Then, a silica gel column was used for separation and purification, and n-hexane was used as an eluent. The solvent was removed by rotary evaporation to collect the product, and finally vacuum dried at room temperature for 12 h to obtain a halogenated compound containing R. The reaction process is as follows:

[0118]

[0119] In another reactor, 0.5 mmol of a halide containing R is dissolved in anhydrous ether solvent. Similarly, the environment is protected by nitrogen and the temperature is set to -78°C. 0.7 mmol of tert-butyl lithium (t-BuLi) solution is slowly added to the reactor to form a first solution, and the temperature is raised to -30°C for reaction for 1 hour to obtain a second solution. The temperature of the second solution is then lowered to -78°C, and a toluene solution of 0.25 mmol of the intermediate compound is added dropwise to the second solution. After the addition is completed, the second solution is heated to room temperature, specifically 25°C, and reacted for 4 hours. After the reaction is completed, a reaction solution is obtained, and the reaction process is as follows:

[0120]

[0121] 30 mL of saturated ammonium chloride solution was added to the reaction solution, followed by extraction and separation with dichloromethane solvent, separation and purification with silica gel column, using n-hexane / dichloromethane as eluent, rotary evaporation to remove the solvent and collect the product, and finally vacuum drying at room temperature for 12 hours to obtain compound M17. The molecular structure identification data of the product are as follows: 1HNMR (300MHz, DMSO), δ (TMS, ppm): 8.98 (d, 4H), 8.7 (s, 2H), 8.24 (s, 4H), 8.11 (d, 4H), 7.75 (m, 4H), 7.68-7.62 (m, 8H), 7.35 (d, 4H), 2.33 (s, 12H), indicating that the product is M17.

[0122] Example 5. Preparation of Compound M20:

[0123] The structural formula of compound M20 is shown below:

[0124]

[0125] 1.2 mmol of bromide containing R1, 1 mmol of borate containing aromatic group and 0.1 mmol of palladium catalyst are added into the reactor, and the reaction environment is made into a protective gas atmosphere. Specifically, vacuum pumping and nitrogen replacement operation can be repeated three times to make the environment into a protective gas atmosphere.

[0126] The reactor includes a 50 mL two-necked bottle containing the bromide of R1. The borate ester containing an aromatic group is The palladium catalyst is Pd(PPh3)4.

[0127] Then, 30 mL of toluene solvent and 3 mL of 2M (mol / L) K2CO3 solution were added to the reactor, and the reaction was carried out at 110°C for 12 h. The reaction solution was then cooled to room temperature, and extracted and separated with dichloromethane solvent. Then, a silica gel column was used for separation and purification, and n-hexane was used as an eluent. The solvent was removed by rotary evaporation to collect the product, and finally vacuum dried at room temperature for 12 h to obtain a halogenated compound containing R. The reaction process is as follows:

[0128]

[0129] In another reactor, 0.5 mmol of a halide containing R is dissolved in anhydrous ether solvent. Similarly, the environment is protected by nitrogen and the temperature is set to -78°C. 0.7 mmol of tert-butyl lithium (t-BuLi) solution is slowly added to the reactor to form a first solution, and the temperature is raised to -30°C for reaction for 1 hour to obtain a second solution. The temperature of the second solution is then lowered to -78°C, and a toluene solution of 0.25 mmol of the intermediate compound is added dropwise to the second solution. After the addition is completed, the second solution is heated to room temperature, specifically 25°C, and reacted for 4 hours. After the reaction is completed, a reaction solution is obtained, and the reaction process is as follows:

[0130]

[0131] 30 mL of saturated ammonium chloride solution was added to the reaction solution, followed by extraction and separation with dichloromethane solvent, separation and purification with silica gel column, and n-hexane / dichloromethane was used as eluent. The solvent was removed by rotary evaporation to collect the product, and finally vacuum dried at room temperature for 12 hours to obtain compound M20. The molecular structure identification data of the product are as follows: 1HNMR (300MHz, DMSO), δ (TMS, ppm): 8.56 (d, 2H), 7.81-7.75 (m, 6H), 7.68 (s, 4H), 7.62-7.53 (m, 4H), 7.48 (m, 4H), 7.38 (m, 4H), 7.35 (m, 4H), 7.28 (m, 2H), 2.33 (s, 12H), indicating that the product is M20.

[0132] In the above, the embodiment of the present invention forms a double boron structure with multiple coordination of boron atoms by introducing two boron atoms and two benzene rings in an organic compound. Since the boron atom itself has a vacant p- orbital, the structure has a strong electronegativity, which can reduce the injection barrier of electrons. At the same time, the electron-withdrawing group is introduced into the double boron structure, which can not only improve the electronegativity, but also reduce the energy level of the material itself, thereby playing a role in blocking holes, and the plane where the structure where the two boron atoms and the benzene rings are connected is separated from the planar structure of the electron-withdrawing group, which can achieve the widening of the band gap of the organic compound itself and the improvement of the triplet energy level. Further, in the embodiment of the present invention, the two boron atoms are directly connected to the two benzene rings and form a ring structure, which improves the molecular rigidity and planarity of the compound, and better planarity contributes to the transmission of electrons, and better rigidity improves the stability of the compound, thereby improving the electronic transmission efficiency and stability of the organic compound.

[0133] In addition, the present invention also provides a light emitting device, please refer to Figure 2 The light emitting device includes a first electrode 10 and a second electrode 20 .

[0134] Optionally, the light-emitting device further includes a light-emitting layer 30 disposed between the first electrode 10 and the second electrode 20, and the light-emitting layer 30 includes the organic compound provided by the embodiment of the present invention.

[0135] Optionally, the light-emitting device further includes a light-emitting layer 30 and an electron transport layer 40 disposed between the first electrode 10 and the second electrode 20 and stacked, wherein the electron transport layer 40 and / or the light-emitting layer 30 include the organic compound provided in the embodiment of the present invention. Figure 2 In the description, a structure in which the light-emitting device includes both the light-emitting layer 30 and the electron transport layer 40 is taken as an example.

[0136] Optionally, the light-emitting device further includes a hole injection layer 50, a hole transport layer 60, an electron blocking layer 70, a hole blocking layer 80 and an electron injection layer 90. Specifically, the light-emitting device includes a hole injection layer 50, a hole transport layer 60, an electron blocking layer 70, a light-emitting layer 30, a hole blocking layer 80, an electron transport layer 40 and an electron injection layer 90 stacked on a first electrode 10, wherein the first electrode 10 may be an anode and the second electrode 20 may be a cathode. At least one of the light-emitting layer 30 and the electron transport layer 40 includes the organic compound provided in an embodiment of the present invention.

[0137] It should be noted that the light-emitting device provided in the embodiment of the present invention may be an OLED display device or a QLED display device, which is not limited herein.

[0138] The embodiment of the present invention further provides a method for manufacturing a light emitting device, and takes an OLED light emitting device as an example for description, the method comprising the following steps:

[0139] First, a tin-doped indium oxide (ITO) substrate is provided, and the ITO layer on the substrate is the first electrode 10, and the substrate is cleaned. Specifically, the cleaning sequence includes: 5% KOH solution ultrasound for 15 minutes, pure water ultrasound for 15 minutes, isopropanol ultrasound for 15 minutes, and then oven drying for 1 hour.

[0140] The substrate was then transferred to a UV ozone cleaning apparatus for surface treatment for 15 minutes, and immediately transferred to a glove box after the treatment. The embodiment of the present invention was subjected to light cleaning before coating other parts, which can greatly improve the wettability of the substrate surface and enhance the adhesion of the substrate surface.

[0141] The evaporation film forming process is performed on the substrate, including sequentially preparing a hole injection layer 50, a hole transport layer 60, an electron blocking layer 70, a light emitting layer 30, a hole blocking layer 80, an electron transport layer 40, an electron injection layer 90 and a second electrode 20 on the substrate, and the specific evaporation process includes: firstly, vacuuming is performed to make the pressure reach 10 -7 Torr, and then slowly increase the current value to slowly increase the rate to After the rate stabilizes, open the baffle to start evaporation.

[0142] Finally, the package is cured by UV light and baked at 80°C for 30 minutes.

[0143] Further, during the evaporation film forming process, the material of the hole injection layer 50 includes HAT-CN (2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene), the material of the hole transport layer 60 includes TAPC (4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline]), the material of the electron blocking layer 70 includes CzSi, and the material of the light-emitting layer 30 includes a host material and a guest material, wherein the host material includes DPEPO (bis[2-((oxy)diphenylphosphino)phenyl]ether), the guest material includes DMAC-DPS (bis[4-(9,9-dimethyl-9,10-dihydroacridine)phenyl]sulfone), the material of the hole blocking layer 80 includes DPEPO (bis[2-((oxy)diphenylphosphino)phenyl]ether), the electron transport layer 40 adopts the organic compound provided by an embodiment of the present invention, the material of the electron injection layer 90 includes LiF, and the material of the second electrode 20 includes Al.

[0144] Among them, the structural formulas of HAT-CN, TAPC, CzSi, DPEPO and DMAC-DPS are as follows:

[0145]

[0146]

[0147] As mentioned above, in the embodiment of the present invention, the light-emitting device corresponding to the organic compound prepared by using compound M1 is recorded as T1, and the light-emitting device corresponding to the organic compound prepared by using compound M2 is recorded as T2. Referring to this method, the light-emitting devices corresponding to the organic compounds prepared by using compounds M3 to M21 are recorded as T3 to T21 respectively, and the light-emitting performance of the light-emitting devices T1 to T21 is measured by using an IV-L test system. The machine model of the test system used is an F-star CS2000A instrument. The results are shown in Table 1 below:

[0148] Table 1 Device performance data table

[0149]

[0150]

[0151] It can be seen from the data in Table 1 that the organic compound provided in the embodiment of the present invention is applied to the light-emitting device, which can make the light-emitting device have higher efficiency, which further shows that the organic compound provided in the embodiment of the present invention has strong electron transmission ability and can improve the electron transmission efficiency.

[0152] According to the test data in Table 1, preferably, R in the organic compound provided in the embodiment of the present invention can be any one of the following:

[0153]

[0154] Preferably, the organic compound provided in the embodiment of the present invention may be any one of the following:

[0155]

[0156] In addition, the organic compound provided by the present invention can be used not only in the field of electroluminescence, but also in the field of photovoltaic cells and the like.

[0157] The embodiment of the present invention further provides a display device, which includes the light-emitting device provided by the embodiment of the present invention. The display device includes wearable devices such as smart bracelets, smart watches, and virtual reality (VR). The display device also includes mobile phones, e-books, e-newspapers, televisions, personal portable computers, and flexible display and lighting devices such as foldable and rollable OLED or QLED.

[0158] In the above embodiments, the description of each embodiment has its own emphasis. For parts that are not described in detail in a certain embodiment, reference can be made to the relevant descriptions of other embodiments.

[0159] The above is a detailed introduction to an organic compound and a preparation method thereof, and a light-emitting device provided in an embodiment of the present invention. Specific examples are used herein to illustrate the principles and implementation methods of the present invention. The description of the above embodiments is only used to help understand the technical solutions and core ideas of the present invention. Ordinary technicians in this field should understand that they can still modify the technical solutions recorded in the aforementioned embodiments, or replace some of the technical features therein with equivalents; and these modifications or replacements do not make the essence of the corresponding technical solutions deviate from the scope of the technical solutions of the embodiments of the present invention.

Claims

1. An organic compound, characterized in that The organic compound includes a compound with a general structural formula as shown in Formula M: Wherein, each R is independently selected from any one of the following:

2. The organic compound according to claim 1, characterized in that The organic compound is any one of the structures shown in the following M1 to M21:

3. A light emitting device, characterized in that: The light emitting device comprises a first electrode, a second electrode and a light emitting layer disposed between the first electrode and the second electrode, wherein the light emitting layer comprises the organic compound according to any one of claims 1 to 2.

4. The light emitting device according to claim 3, characterized in that: The light-emitting device includes a hole injection layer, a hole transport layer, an electron blocking layer, the light-emitting layer, the hole blocking layer, the electron transport layer, the electron injection layer and the second electrode stacked on the first electrode, wherein the first electrode is an anode and the second electrode is a cathode.

5. A light emitting device, characterized in that: The light-emitting device comprises a first electrode, a second electrode, and a light-emitting layer and an electron transport layer which are stacked and arranged between the first electrode and the second electrode, and the electron transport layer and / or the light-emitting layer comprises the organic compound according to any one of claims 1 to 2.

6. The light emitting device according to claim 5, characterized in that: The light-emitting device includes a hole injection layer, a hole transport layer, an electron blocking layer, the light-emitting layer, the hole blocking layer, the electron transport layer, the electron injection layer and the second electrode stacked on the first electrode, wherein the first electrode is an anode and the second electrode is a cathode.

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