Organic Compounds, Their Preparation Methods, Mixtures, Compositions and Semiconductor Devices

Abstract

The present application discloses an organic compound, a preparation method thereof, a mixture, a composition and a semiconductor device. By using a first reactant and a second reactant to generate a first intermediate product, a third reactant and the first intermediate product to generate a second intermediate product, a fourth reactant and the second intermediate product to generate a third intermediate product, and a fifth reactant and the third intermediate product to generate an organic compound, and replacing the covalent bond in the fluorene unit in the prior art with a hydrogen bond formed by the hydrogen in the amino group and the lone pair electrons on the nitrogen atom, a preparation process of a polymer material with a simple synthesis route is realized.

Description

Technical Field

[0001] The present application relates to the field of display technologies, and particularly relates to an organic compound, a preparation method thereof, a mixture, a composition and a semiconductor device. Background Art

[0002] Organic Light-Emitting Diodes (OLEDs) have advantages such as fast response speed, high contrast ratio, wide viewing angle, flexibility, etc. With the continuous development of display technologies, the yield and production cost of OLEDs have been effectively controlled, and their market share is gradually increasing. Very similar to OLEDs, Quantum Dot Light Emitting Diodes (QLEDs) also have advantages such as fast response speed, high contrast ratio, wide viewing angle, flexibility, etc., and have a wider color gamut.

[0003] In the film layer structure of OLED devices and QLED devices, the hole transport layer can significantly reduce the hole transport energy barrier, lower the voltage of the device, and improve the efficiency of the device, thus playing an important role in the device. In the prior art, polyfluorene-based polymer materials are usually used as hole transport materials, but the synthesis route of fluorene is relatively complex. Summary of the Invention

[0004] Embodiments of the present application provide an organic compound, a preparation method thereof, a mixture, a composition and a semiconductor device to solve the technical problem of the complex synthesis route of materials in the prior art.

[0005] Embodiments of the present application provide an organic compound, and the structural formula of the organic compound is one of wherein the structural formula of the A 1 group is one of wherein the structural formula of the A 2 group, the structural formula of the A 11 group, and the structural formula of the A 12 group are independently selected from one of ;

[0006] wherein, the A 2 group is different from the A 1 group, and the A 11 group and the A12 The groups are different, the R group is a hydrogen atom or an alkyl group, n > 1 and is an integer, and 0 < m < 1.

[0007] Optionally, in some embodiments of the present application, the structural formula of the organic compound is One of them.

[0008] Optionally, in some embodiments of the present application, the chemical formula of the organic compound is One of them.

[0009] The embodiments of the present application provide a method for preparing an organic compound, which includes the following steps:

[0010] Provide a first reactant and a second reactant, and the first reactant and the second reactant react to form a first intermediate product. Among them, the structural formula of the first reactant is One of them, and the structural formula of the second reactant is One of them, and the X group is a halogen;

[0011] Provide a third reactant, and the third reactant and the first intermediate product react to form a second intermediate product. Among them, the third reactant is a compound containing an amino group or an aniline group, and the second intermediate product is a compound containing an A 1 group, and the R group is a hydrogen atom or an alkyl group;

[0012] Provide a fourth reactant, and the fourth reactant and the second intermediate product react to form a third intermediate product. Among them, the fourth reactant is liquid bromine;

[0013] Provide a fifth reactant, and the fifth reactant and the third intermediate product react to form an organic compound. Among them, the structural formula of the fifth reactant is One of them, the chemical formula of the A2 group is One of them, the A 2 group and the A 1 group are different, and the structural formula of the organic compound is n > 1 and is an integer; or

[0014] A fifth reactant and a sixth reactant are provided, and the fifth reactant, the sixth reactant and the third intermediate react to form an organic compound, wherein the structural formula of the fifth reactant is The structural formula of the sixth reactant The A 11 group and the A 12 groups' structural formulas are each independently selected from one of them, the A 11 group and the A 12 group are different, and the structural formula of the organic compound is 0 < m < 1.

[0015] Optionally, in some embodiments of the present application, the structural formula of the organic compound is one of them.

[0016] Optionally, in some embodiments of the present application, the chemical formula of the organic compound is one of them.

[0017] Optionally, in some embodiments of the present application, in the reaction of the first reactant and the second reactant to form the first intermediate, the corresponding relationship between the molar amount of the first reactant and the molar amount of the second reactant is that 20 mmol of the first reactant corresponds to 5 mmol - 15 mmol of the second reactant; and / or

[0018] In the reaction of the third reactant and the first intermediate to form the second intermediate, the corresponding relationship between the molar amount of the third reactant and the molar amount of the first intermediate is that 25 mmol of the third reactant corresponds to 5 mmol - 15 mmol of the first intermediate.

[0019] Optionally, in some embodiments of the present application, in the reaction of the fourth reactant and the second intermediate to form the third intermediate, the corresponding relationship between the molar amount of the fourth reactant and the molar amount of the second intermediate is that 30 mmol of the fourth reactant corresponds to 1 mmol - 20 mmol of the second intermediate.

[0020] Optionally, in some embodiments of the present application, in the reaction of the fifth reactant and the third intermediate to form the organic compound, the corresponding relationship between the molar amount of the fifth reactant and the molar amount of the third intermediate is that 18 mmol of the fifth reactant corresponds to 1 mmol - 15 mmol of the third intermediate; or

[0021] in the reaction of the fifth reactant, the sixth reactant and the third intermediate to form the organic compound, the corresponding relationship between the molar amount of the fifth reactant, the molar amount of the sixth reactant and the molar amount of the third intermediate is that 1 - 20 mmol of the fifth reactant and 1 - 20 mmol of the sixth reactant correspond to 25 mmol of the third intermediate.

[0022] The embodiments of the present application further provide a mixture, which includes the organic compound as described in any of the foregoing embodiments, and at least one organic functional material, and the organic functional material is selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a light emitting material, a host material or an organic dye.

[0023] The embodiments of the present application further provide a composition, which includes the organic compound as described in any of the foregoing embodiments or the mixture as described in the foregoing embodiments, and at least one organic solvent.

[0024] The embodiments of the present application further provide a semiconductor device, which includes a first electrode, a second electrode, and one or more functional layers located between the first electrode and the second electrode, and the functional layer includes the organic compound as described in any of the foregoing embodiments, or the mixture as described in the foregoing embodiments, or is prepared from the composition as described in the foregoing embodiments.

[0025] The present application provides an organic compound, a preparation method thereof, a mixture, a composition and a semiconductor device. By using a first reactant and a second reactant to form a first intermediate, a third reactant and the first intermediate to form a second intermediate, a fourth reactant and the second intermediate to form a third intermediate, and a fifth reactant and the third intermediate to form an organic compound, and using the hydrogen bond formed by the hydrogen in the amino group and the lone pair electrons on the nitrogen atom to replace the covalent bond in the fluorene unit in the prior art, a preparation process of a polymer material with a simple synthesis route is realized. Description of the Drawings

[0026] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following will briefly introduce the drawings required for the description of the embodiments. Obviously, the following drawings are only some embodiments of the present application. For those skilled in the art, other drawings can be obtained based on these drawings without creative efforts.

[0027] Figure 1 is a graph of the current density versus voltage of the S1 device and the T1 device - T6 devices in this application.

[0028] Figure 2 is a graph of the current efficiency versus current density of the S1 device and the T1 device - T6 devices in this application.

[0029] Figure 3 is a schematic structural diagram of the semiconductor device provided by this application. Detailed implementation manners

[0030] Next, the technical solutions in the embodiments of this application will be clearly and completely described in conjunction with the accompanying drawings in the embodiments of this application. Obviously, the described embodiments are only a part of the embodiments of this application, rather than all of the embodiments. Based on the embodiments in this application, all other embodiments obtained by those skilled in the art without making creative efforts belong to the scope of protection of this application. In addition, it should be understood that the specific implementation manners described here are only used to illustrate and explain this application, and are not used to limit this application. In this application, unless otherwise stated, the orientation words such as "upper", "lower", "left", and "right" usually refer to the upper, lower, left, and right in the actual use or working state of the device, specifically the drawing direction in the accompanying drawings; and "inner" and "outer" are with respect to the contour of the device.

[0031] This application provides an organic compound, its preparation method, mixture, composition, and semiconductor device. The following will be described in detail respectively. It should be noted that the description order of the following embodiments does not limit the preferred order of the embodiments.

[0032] It should be noted that the organic compound in this application can be used as a hole injection material for preparing a hole injection layer; the organic compound in this application can also be used as a hole transport material for preparing a hole transport layer. The application scenario of the organic compound can be selected according to actual application requirements, and this application does not limit this.

[0033] It can be understood that in this application, the "*" in all structural formulas refers to the connection site for forming a chemical bond with other groups.

[0034] This application provides an organic compound, and the structural formula of the organic compound is one of. The A 1 group has a structural formula of one of. The A 2 group, the A11 The group and the A 12 Structural formulas of the groups are each independently selected from one of; the A 2 group is different from the A 1 group. The A 11 group and the A 12 group are different. The R group is a hydrogen atom or an alkyl group. n > 1 and is an integer, 0 < m < 1.

[0035] Wherein, when the R group is an alkyl group, the number of carbon atoms in the alkyl group ranges from 1 to 18.

[0036] In some embodiments of the present application, the structural formula of the organic compound is one of.

[0037] In some embodiments of the present application, the chemical formula of the organic compound is one of.

[0038] The present application provides a method for preparing an organic compound, which includes the following steps:

[0039] B1: Provide a first reactant and a second reactant, and the first reactant and the second reactant react to form a first intermediate product. Wherein, the structural formula of the first reactant is one of, the structural formula of the second reactant is one of, the structural formula of the first intermediate product is one of, and the X group is a halogen.

[0040] In some embodiments, the X group can be a Br atom, a Cl atom or an I atom.

[0041] In some embodiments, when the structural formula of the first reactant is and the structural formula of the second reactant is the reaction general formula for the first reactant and the second reactant to react to form the first intermediate product is:

[0042]

[0043] In some embodiments, when the structural formula of the first reactant is the structural formula of the second reactant is the reaction general formula for the first reactant and the second reactant to react to form the first intermediate is:

[0044]

[0045] In some embodiments, when the structural formula of the first reactant is the structural formula of the second reactant is the reaction general formula for the first reactant and the second reactant to react to form the first intermediate is:

[0046]

[0047] In some embodiments, when the structural formula of the first reactant is the structural formula of the second reactant is the reaction general formula for the first reactant and the second reactant to react to form the first intermediate is:

[0048]

[0049] In some embodiments of the present application, the first reactant and the second reactant are added to a two-necked flask, a first additive and a first solvent are added, and the reaction is carried out under reflux heating in a nitrogen atmosphere to obtain a mixture including the first intermediate, and the mixture is separated and purified to obtain the first intermediate.

[0050] In some embodiments, in the reaction of the first reactant and the second reactant to form the first intermediate, the corresponding relationship between the molar amount of the first reactant and the molar amount of the second reactant is that 20 mmol of the first reactant corresponds to 5 mmol - 15 mmol of the second reactant. Specifically, the corresponding relationship between the molar amount of the first reactant and the molar amount of the second reactant can be that 20 mmol of the first reactant corresponds to 10 mmol of the second reactant. The corresponding relationship between the molar amount of the first reactant and the molar amount of the second reactant can also be that 20 mmol of the first reactant corresponds to 5 mmol of the second reactant.

[0051] In some embodiments, the first reactant and the second reactant react in the first solvent to form the first intermediate. The first solvent includes one or a combination of several of water, acetone, n-butanol, ethyl formate, methyl acetate, peroxypropionic acid, peracetic acid, diethyl ether, chloroform, tetrahydrofuran, acetic acid, formic acid, formaldehyde, hydroxypropionic acid, mercaptoacetic acid, indole-3-acetic acid, methyl formate, 2-hydroxyacetaldehyde.

[0052] In some embodiments, the volume of the first solvent is 20 mL - 200 mL, such as 20 mL, 50 mL, 80 mL, 100 mL, 120 mL, 150 mL, 180 mL or 200 mL, etc.

[0053] In some embodiments, the first solvent contains the first additive. The first additive includes one or a combination of several of sodium carbonate, potassium carbonate, tetrakis(triphenylphosphine)palladium, n-butyllithium, potassium hydroxide, sodium hydroxide and sodium tert-butoxide.

[0054] In some embodiments, when the first reactant and the second reactant react to form the first intermediate, the reaction temperature is 50°C - 150°C, such as 50°C, 60°C, 70°C, 80°C, 90°C, 100°C, 120°C or 150°C, etc. The reaction time is 12 h - 36 h, such as 12 h, 15 h, 18 h, 20 h, 24 h, 30 h, 32 h or 36 h, etc.

[0055] B2: Provide a third reactant, which reacts with the first intermediate to form a second intermediate. Among them, the third reactant is a compound containing an amino group or an anilino group, and the second intermediate is a compound containing an A 1 group, and the structural formula of the second intermediate is one of, and the A 1 group has a structural formula of one of, and the R group is a hydrogen atom or an alkyl group.

[0056] In some embodiments, when the R group is an alkyl group, the number of carbon atoms in the alkyl group is 1 - 18.

[0057] In some embodiments, the structural formula of the third reactant is R-NH 2 or

[0058] In some embodiments of the present application, the third reactant and the first intermediate product are added to a two-necked flask, and a second additive and a second solvent are added for reaction. The reaction is carried out under reflux by heating in a nitrogen atmosphere to obtain a mixture including the second intermediate product. The mixture is separated and purified to obtain the second intermediate product.

[0059] In some embodiments, in the reaction of the third reactant and the first intermediate product to form the second intermediate product, the corresponding relationship between the molar amount of the third reactant and the molar amount of the first intermediate product is that 25 mmol of the third reactant corresponds to 5 mmol - 15 mmol of the first intermediate product. Specifically, the corresponding relationship between the molar amount of the third reactant and the molar amount of the first intermediate product can be that 12 mmol of the third reactant corresponds to 10 mmol of the first intermediate product. The corresponding relationship between the molar amount of the third reactant and the molar amount of the first intermediate product can also be that 24 mmol of the third reactant corresponds to 10 mmol of the first intermediate product.

[0060] In some embodiments, the third reactant and the first intermediate product react in the second solvent to form the second intermediate product. The second solvent includes one or a combination of several of dichloroethane, isopropyl ether, butyl acetate, diethyl ether, ethyl acetate, n-pentane, n-butanol, phenol, dichloromethane, chloroform, tert-butanol, and tetrahydrofuran.

[0061] In some embodiments, the volume of the second solvent is 20 mL - 200 mL, such as 20 mL, 50 mL, 80 mL, 100 mL, 120 mL, 150 mL, 180 mL, or 200 mL, etc.

[0062] In some embodiments, the second additive is present in the second solvent. The second additive includes one or a combination of several of sodium carbonate, potassium carbonate, potassium hydroxide, sodium hydroxide, and sodium tert-butoxide.

[0063] In some embodiments, in the reaction of the third reactant and the first intermediate product to form the second intermediate product, the reaction temperature is 30°C - 120°C, such as 30°C, 40°C, 50°C, 60°C, 70°C, 80°C, 90°C, 110°C, or 120°C, etc. The reaction time is 8 h - 24 h, such as 8 h, 10 h, 12 h, 15 h, 18 h, 20 h, or 24 h, etc.

[0064] B3: Provide a fourth reactant, and the fourth reactant reacts with the second intermediate product to form a third intermediate product, wherein the fourth reactant is liquid bromine, and the structural formula of the third intermediate product is Br - A 1-Br

[0065] In some embodiments, the fourth reactant and the second intermediate are added to a two-necked flask, and a third additive and a third solvent are added for reaction. The reaction is carried out under reflux heating in a nitrogen atmosphere to obtain a mixture containing a third intermediate, and the mixture is separated and purified to produce the third intermediate.

[0066] In some embodiments, when the fourth reactant and the second intermediate react to form the third intermediate, the corresponding relationship between the molar amount of the fourth reactant and the molar amount of the second intermediate is that 30 mmol of the fourth reactant corresponds to 1 mmol - 20 mmol of the second intermediate. Specifically, the corresponding relationship between the molar amount of the fourth reactant and the molar amount of the second intermediate can be that 30 mmol of the fourth reactant corresponds to 14 mmol of the second intermediate. The corresponding relationship between the molar amount of the fourth reactant and the molar amount of the second intermediate can also be that 30 mmol of the fourth reactant corresponds to 8 mmol of the second intermediate.

[0067] In some embodiments, the fourth reactant and the second intermediate react in the third solvent to form the third intermediate. The third solvent includes one or a combination of several of dichloroethane, isopropyl ether, butyl acetate, diethyl ether, ethyl acetate, n-pentane, n-butanol, phenol, dichloromethane, chloroform, tert-butanol, and tetrahydrofuran.

[0068] In some embodiments, the volume of the third solvent is 20 mL - 200 mL, such as 20 mL, 50 mL, 80 mL, 100 mL, 120 mL, 150 mL, 180 mL, or 200 mL, etc.

[0069] In some embodiments, the third additive is present in the third solvent. The third additive includes one or a combination of several of sodium methoxide, sodium ethoxide, iron(III) bromide, and iron(II) bromide.

[0070] In some embodiments, when the fourth reactant and the second intermediate react to form the third intermediate, the reaction temperature is 50°C - 160°C, such as 50°C, 60°C, 80°C, 100°C, 110°C, 120°C, 150°C, or 160°C, etc. The reaction time is 8 h - 24 h, such as 8 h, 10 h, 12 h, 15 h, 18 h, 20 h, or 24 h, etc.

[0071] B4: Provide a fifth reactant, and the fifth reactant reacts with the third intermediate to form an organic compound, wherein the structural formula of the fifth reactant is one of the following, the chemical formula of the A2 group is one of the following, the A 2 group and the A 1 group are different, the structural formula of the organic compound is n > 1 and is an integer.

[0072] In some embodiments, when the structural formula of the fifth reactant is the reaction general formula for the fifth reactant and the third intermediate to react to form an organic compound is:

[0073]

[0074] In some embodiments, when the structural formula of the fifth reactant is the reaction general formula for the fifth reactant and the third intermediate to react to form an organic compound is:

[0075]

[0076] In some embodiments, the structural formula of the organic compound can be

[0077] In some embodiments, add the fifth reactant and the third intermediate to a two-necked flask, add a fourth additive and a fourth solvent to react, heat under reflux in a nitrogen atmosphere to react, obtain a mixture including the organic compound, and separate and purify the mixture to obtain the organic compound.

[0078] In some embodiments, in the reaction of the fifth reactant and the third intermediate to form the organic compound, the corresponding relationship between the molar amount of the fifth reactant and the molar amount of the third intermediate is that 18 mmol of the fifth reactant corresponds to 1 mmol - 15 mmol of the third intermediate. Specifically, the corresponding relationship between the molar amount of the fifth reactant and the molar amount of the third intermediate can be that 15 mmol of the fifth reactant corresponds to 15 mmol of the third intermediate. The corresponding relationship between the molar amount of the fifth reactant and the molar amount of the third intermediate can also be that 15 mmol of the fifth reactant corresponds to 5 mmol of the third intermediate.

[0079] In some embodiments, the fifth reactant and the third intermediate react in the fourth solvent to form the organic compound. The fourth solvent includes one or a combination of several of water, acetone, n-butanol, ethyl formate, methyl acetate, peroxypropionic acid, peracetic acid, diethyl ether, chloroform, tetrahydrofuran, acetic acid, formic acid, formaldehyde, hydroxypropionic acid, mercaptoacetic acid, indole-3-acetic acid, toluene, 1-methyl-2-pyrrolidone, methyl formate, 2-hydroxyacetaldehyde.

[0080] In some embodiments, the volume of the fourth solvent is 20 mL - 200 mL, such as 20 mL, 50 mL, 80 mL, 100 mL, 120 mL, 150 mL, 180 mL or 200 mL, etc.

[0081] In some embodiments, the fourth solvent contains the fourth additive. The fourth additive includes one or a combination of several of sodium carbonate, potassium carbonate, tetrakis(triphenylphosphine)palladium, n-butyllithium, potassium hydroxide, sodium hydroxide and sodium tert-butoxide.

[0082] In some embodiments, in the reaction of the fifth reactant and the third intermediate to form the organic compound, the reaction temperature is 50 °C - 150 °C, such as 50 °C, 60 °C, 70 °C, 80 °C, 90 °C, 100 °C, 120 °C or 150 °C, etc. The reaction time is 12 h - 36 h, such as 12 h, 15 h, 18 h, 20 h, 24 h, 30 h, 32 h, 30 h or 36 h, etc.

[0083] In some embodiments, step B4 can also be:

[0084] B4: Provide a fifth reactant and a sixth reactant, and the fifth reactant, the sixth reactant and the third intermediate react to form an organic compound, wherein the structural formula of the fifth reactant is The structural formula of the sixth reactant The A 11 group and the A 12 groups are independently selected from one of, the A 11 group and the A 12 groups are different, and the structural formula of the organic compound is 0 < m < 1.

[0085] In some embodiments, the reaction general formula for the fifth reactant, the sixth reactant and the third intermediate to react to form an organic compound is:

[0086]

[0087] In some embodiments, the structural formula of the organic compound may be one of the following.

[0088] In some embodiments, the fifth reactant, the sixth reactant, and the third intermediate are added to a two-necked flask, and a fourth additive and a fourth solvent are added for reaction. The reaction is carried out under reflux heating in a nitrogen atmosphere to obtain a mixture containing the organic compound, and the mixture is separated and purified to obtain the organic compound.

[0089] In some embodiments, when the fifth reactant, the sixth reactant, and the third intermediate react to form the organic compound, the corresponding relationship between the molar amounts of the fifth reactant, the sixth reactant, and the third intermediate is 1-20 mmol of the fifth reactant and 1-20 mmol of the sixth reactant corresponding to 25 mmol of the third intermediate. Specifically, the corresponding relationship between the molar amounts of the fifth reactant, the sixth reactant, and the third intermediate may be 10 mmol of the fifth reactant, 10 mmol of the sixth reactant corresponding to 20 mmol of the third intermediate. The corresponding relationship between the molar amounts of the fifth reactant, the sixth reactant, and the third intermediate may also be 2 mmol of the fifth reactant, 8 mmol of the sixth reactant corresponding to 10 mmol of the third intermediate.

[0090] In some embodiments, the fifth reactant, the sixth reactant, and the third intermediate react in the fourth solvent to form the organic compound. The fourth solvent includes one or a combination of several of water, acetone, n-butanol, ethyl formate, methyl acetate, peroxypropionic acid, peracetic acid, ether, chloroform, tetrahydrofuran, acetic acid, formic acid, formaldehyde, hydroxypropionic acid, mercaptoacetic acid, indole-3-acetic acid, toluene, 1-methyl-2-pyrrolidone, methyl formate, 2-hydroxyacetaldehyde.

[0091] In some embodiments, the volume of the fourth solvent is 20 mL - 200 mL, such as 20 mL, 50 mL, 80 mL, 100 mL, 120 mL, 150 mL, 180 mL, or 200 mL, etc.

[0092] In some embodiments, the fourth additive is present in the fourth solvent. The fourth additive comprises one or a combination of several of sodium carbonate, potassium carbonate, tetrakis(triphenylphosphine)palladium, n-butyllithium, potassium hydroxide, sodium hydroxide, and sodium tert-butoxide.

[0093] In some embodiments, when the fifth reactant, the sixth reactant, and the third intermediate react to form the organic compound, the reaction temperature is 50°C - 150°C, such as 50°C, 60°C, 70°C, 80°C, 90°C, 100°C, 120°C, or 150°C, etc. The reaction time is 12 h - 36 h, such as 12 h, 15 h, 18 h, 20 h, 24 h, 30 h, 32 h, 30 h, or 36 h, etc.

[0094] The preparation method of the organic compound provided by the present application will be further described below by way of examples. Among them, in the following examples, the organic compound is a hole transport material.

[0095] Example 1

[0096] In this embodiment, the first reactant is The second reactant is The third reactant is C 4 H 9 NH 2 , the fourth reactant is liquid bromine Br 2 , the fifth reactant is

[0097] (1) Add 2 mmol of the first reactant, 1 mmol of the second reactant, 0.05 mmol of tetrakis(triphenylphosphine)palladium, and 3 mmol of sodium carbonate to a 100 mL two-necked flask in sequence. Add a magnetic stir bar and perform vacuum replacement with nitrogen to make the inside of the reaction flask in a nitrogen atmosphere; add 50 mL of a mixed solvent of tetrahydrofuran / deionized water (V / V = 3:1), and reflux and react at 70°C for 24 h; cool to room temperature, place the above reaction solution in dichloromethane, extract with water multiple times, and then dry with anhydrous MgSO 4 , filter, rotary evaporate to remove the solvent in the above mixed solution, use n-hexane / dichloromethane as the eluent, rotary evaporate to remove the eluent, and obtain the first intermediate Among them, the reaction formula for the first reactant and the second reactant to react to form the first intermediate is:

[0098]

[0099] In this embodiment, the yield of the first intermediate is 66%. 1H NMR (500 MHz, CDCl 3), δ(TMS, ppm): 8.61 - 8.59 (d, 1H), 8.20 - 8.17 (d, 1H), 7.71 - 7.69 (d, 1H), 7.46 - 7.41 (m, 2H), 7.37 - 7.35 (d, 1H), 7.20 - 7.17 (d, 1H), 7.01 - 6.98 (d, 1H).

[0100] (2) 1.2 mmol of the third reactant, 1.0 mmol of the first intermediate, and 1.5 mmol of potassium carbonate were successively added to a 100 mL two-necked flask. A magnetic stir bar was added, and the vacuum was replaced with nitrogen to make the reaction flask under a nitrogen atmosphere; 50 mL of acetone was added, and the reaction was refluxed at 50 °C for 12 h; cooled to room temperature, the above reaction solution was placed in dichloromethane and extracted with water multiple times. The organic phase was taken, and then dried with anhydrous MgSO 4 After drying, filtration, and rotary evaporation to remove the solvent from the above mixture, n-hexane / dichloromethane was used as the eluent, and the eluent was rotary evaporated to obtain the second intermediate Among them, the reaction formula for the third reactant and the first intermediate to react to form the second intermediate is:

[0101]

[0102] In this example, the second intermediate had a yield of 83%. 1H NMR (500 MHz, CDCl 3 ), δ(TMS, ppm): 9.37 - 9.35 (d, 1H), 8.56 - 8.53 (d, 1H), 7.53 - 7.51 (m, 1H), 7.26 - 7.22 (m, 2H), 7.07 - 7.01 (m, 2H), 6.88 - 6.82 (m, 1H), 4.03 (s, 1H), 3.37 - 3.35 (m, 2H), 1.49 - 1.31 (m, 4H), 0.92 - 0.89 (m, 3H).

[0103] (3) 1 mmol of the second intermediate and 0.05 mmol of iron tribromide were successively added to a 100 mL two-necked flask. A magnetic stir bar was added, and the vacuum was replaced with nitrogen to make the reaction flask under a nitrogen atmosphere. 50 mL of chloroform was added, and 2.1 mmol of the fourth reactant was slowly added dropwise. The reaction was refluxed at 80 °C for 12 h; the above reaction solution was extracted with water multiple times. The organic phase was taken, and then dried with anhydrous MgSO 4 After drying, filtration, and rotary evaporation to remove the solvent from the above mixture, n-hexane / dichloromethane was used as the eluent, and the eluent was rotary evaporated to obtain the third intermediate Among them, the reaction formula for the fourth reactant and the second intermediate to react to form the third intermediate is:

[0104]

[0105] In this example, the yield of the third intermediate is 63%. 1H NMR (500 MHz, CDCl 3 ), δ (TMS, ppm): 8.51 - 8.48 (s, 1H), 8.33 - 8.31 (d, 1H), 7.97 - 7.93 (d, 1H), 7.53 - 7.51 (d, 1H), 7.00 - 6.97 (d, 1H), 6.73 (s, 1H),, 4.03 (s, 1H), 3.37 - 3.35 (m, 2H), 1.49 - 1.31 (m, 4H), 0.92 - 0.89 (m, 3H).

[0106] (4) Add 1 mmol of the third intermediate, 1 mmol of the fifth reactant, 0.05 mmol of tetrakis(triphenylphosphine)palladium, and 3 mmol of sodium carbonate successively to a 100 mL two-necked flask. Add a magnetic stir bar, perform vacuum evacuation and nitrogen replacement operations to make the inside of the reaction flask in a nitrogen atmosphere. Add 50 mL of a mixed solvent of tetrahydrofuran / deionized water (V / V = 3:1), and reflux the reaction at 70 °C for 24 h; cool to room temperature, place the above reaction solution in dichloromethane, extract it with water multiple times, and then dry it with anhydrous MgSO 4 Filter, rotary evaporate to remove the solvent in the above mixed solution, use ethanol, ethyl acetate, and petroleum ether as eluents, rotary evaporate to remove the eluents, then dissolve the solid obtained by rotary evaporation in chlorobenzene, filter, and rotary evaporate to remove the solvent in the filtrate to obtain a hole transport material (hereinafter referred to as T1). Among them, the reaction formula for the fifth reactant and the third intermediate to react to form the hole transport material is:

[0107]

[0108] In this example, the yield of the hole transport material T1 is 66%. The number average molecular weight Mn of T1 is 29025 g / mol. The dispersity index PDI of T1 is 2.03.

[0109] Example 2

[0110] In this example, the first reactant is The second reactant is The third reactant is C 4 H 9 NH 2 , the fourth reactant is liquid bromine Br 2 , the fifth reactant is

[0111] (1) 4 mmol of the first reactant, 1 mmol of the second reactant, 0.05 mmol of tetrakis(triphenylphosphine)palladium, and 3 mmol of sodium carbonate were successively added to a 100 mL two-necked flask. A magnetic stir bar was added, and the vacuum was replaced with nitrogen to create a nitrogen atmosphere inside the reaction flask. 50 mL of a mixed solvent of tetrahydrofuran / deionized water (V / V = 3:1) was added, and the reaction was refluxed at 70 °C for 24 h; cooled to room temperature, the above reaction solution was placed in dichloromethane, extracted with water multiple times, and then dried with anhydrous MgSO 4 and filtered. The solvent in the above mixture was removed by rotary evaporation. Using n-hexane / dichloromethane as the eluent, the eluent was removed by rotary evaporation to obtain the first intermediate product Among them, the reaction formula for the first reactant and the second reactant to react to form the first intermediate product is:

[0112]

[0113] In this example, the yield of the first intermediate product was 66%. 1H NMR (500 MHz, CDCl 3 ), δ (TMS, ppm): 8.80 (s, 2H), 7.69 - 7.65 (m, 4H), 7.47 - 7.44 (m, 2H), 7.31 - 7.28 (m, 2H).

[0114] (2) 1.2 mmol of the third reactant, 1.0 mmol of the first intermediate product, and 1.5 mmol of potassium carbonate were successively added to a 100 mL two-necked flask. A magnetic stir bar was added, and the vacuum was replaced with nitrogen to create a nitrogen atmosphere inside the reaction flask; 50 mL of acetone was added, and the reaction was refluxed at 50 °C for 12 h; cooled to room temperature, the above reaction solution was placed in dichloromethane, extracted with water multiple times, the organic phase was taken, and then dried with anhydrous MgSO 4 and filtered. The solvent in the above mixture was removed by rotary evaporation. Using n-hexane / dichloromethane as the eluent, the eluent was removed by rotary evaporation to obtain the second intermediate product Among them, the reaction formula for the third reactant and the first intermediate product to react to form the second intermediate product is:

[0115]

[0116] In this example, the yield of the second intermediate product was 78%. 1H NMR (500 MHz, CDCl 3), δ(TMS, ppm): 8.86 (d, 2H), 8.79 (s, 2H), 7.83 - 7.76 (m, 2H), 7.05 - 7.02 (d, 2H), 6.88 - 6.82 (m, 2H), 4.03 (s, 2H), 3.37 - 3.35 (m, 4H), 1.49 - 1.31 (m, 8H), 0.92 - 0.89 (m, 6H).

[0117] (3) Add 1 mmol of the second intermediate and 0.05 mmol of iron tribromide successively to a 100 mL two-necked flask, add a magnetic stir bar, perform vacuum evacuation and nitrogen replacement operations to make the reaction flask under a nitrogen atmosphere, add 50 mL of chloroform, slowly dropwise add 2.1 mmol of the fourth reactant, and reflux the reaction at 80 °C for 12 h; extract the above reaction solution with water multiple times, take the organic phase, and then use anhydrous MgSO 4 dry, filter, rotary evaporate to remove the solvent in the above mixture, use n-hexane / dichloromethane as the eluent, rotary evaporate to remove the eluent, and obtain the third intermediate Among them, the reaction formula for the fourth reactant and the second intermediate to react to form the third intermediate is:

[0118]

[0119] In this example, the third intermediate has a yield of 63%. 1H NMR (500 MHz, CDCl 3 ), δ(TMS, ppm): 8.79 (s, 2H), 7.48 - 7.46 (d, 2H), 7.01 - 6.98 (d, 2H), 6.72 (s, 2H), 4.03 (s, 2H), 3.37 - 3.35 (m, 4H), 1.49 - 1.31 (m, 8H), 0.92 - 0.89 (m, 6H).

[0120] (4) Add 1 mmol of the third intermediate, 1 mmol of the fifth reactant, 0.05 mmol of tetrakis(triphenylphosphine)palladium, and 3 mmol of sodium carbonate successively to a 100 mL two-necked flask, add a magnetic stir bar, perform vacuum evacuation and nitrogen replacement operations to make the reaction flask under a nitrogen atmosphere, add 50 mL of a mixed solvent of tetrahydrofuran / deionized water (V / V = 3:1), and reflux the reaction at 70 °C for 24 h; cool to room temperature, place the above reaction solution in dichloromethane, extract with water multiple times, and then use anhydrous MgSO 4 dry, filter, rotary evaporate to remove the solvent in the above mixture, use ethanol, ethyl acetate, and petroleum ether as the eluent, rotary evaporate to remove the eluent, and then dissolve the solid obtained by rotary evaporation in chlorobenzene, filter, and rotary evaporate to remove the solvent in the filtrate to obtain the hole functional material (hereinafter referred to as T2). Among them, the reaction formula for the fifth reactant and the third intermediate to react to form the hole functional material is:

[0121]

[0122] In this example, the yield of the hole functional material T2 is 58%. The number average molecular weight Mn of T2 is 37895 g / mol. The dispersity index PDI of T2 is 1.81.

[0123] Example 3

[0124] In this example, the first reactant is The second reactant is The third reactant is The fourth reactant is liquid bromine Br 2 , and the fifth reactant is

[0125] Step (1) of this example is the same as step (1) in Example 1 and will not be elaborated here. Steps (2) - (4) are as follows:

[0126] (2) Add 1.2 mmol of the third reactant, 1.0 mmol of the first intermediate, and 1.5 mmol of potassium carbonate to a 100 mL two-necked flask in sequence. Add a magnetic stirrer and perform vacuum evacuation and nitrogen replacement operations to make the reaction flask under a nitrogen atmosphere; add 50 mL of acetone and reflux at 50 °C for 12 h; cool to room temperature, place the above reaction solution in dichloromethane, extract with water multiple times, take the organic phase, and then use anhydrous MgSO 4 Dry, filter, rotary evaporate to remove the solvent in the above mixture, use n-hexane / dichloromethane as the eluent, rotary evaporate to remove the eluent, and obtain the second intermediate Among them, the reaction formula for the third reactant and the first intermediate to react to form the second intermediate is:

[0127]

[0128] In this example, the second intermediate has a yield of 86%. 1H NMR (500 MHz, CDCl 3 ), δ (TMS, ppm): 9.37 - 9.35 (d, 1H), 8.56 - 8.53 (d, 1H), 7.53 - 7.51 (m, 1H), 7.36 - 7.32 (d, 2H), 7.01 - 6.97 (m, 3H), 6.74 - 6.72 (d, 1H), 4.03 (s, 1H), 1.35 (m, 9H).

[0129] (3) Add 1 mmol of the second intermediate product and 0.05 mmol of iron tribromide to a 100 mL two-necked flask in sequence. Add a magnetic stirring bar, perform vacuum evacuation and nitrogen replacement operations to make the reaction flask under a nitrogen atmosphere. Add 50 mL of chloroform, slowly dropwise add 2.1 mmol of the fourth reactant, and reflux the reaction at 80 °C for 12 h; extract the above reaction solution with water multiple times, take the organic phase, and then use anhydrous MgSO 4 dry, filter, rotary evaporate to remove the solvent in the above mixture, use n-hexane / dichloromethane as the eluent, rotary evaporate to remove the eluent, and obtain the third intermediate product Among them, the reaction formula for the fourth reactant and the second intermediate product to react to form the third intermediate product is:

[0130]

[0131] In this example, the third intermediate product has a yield of 58%. 1H NMR (500 MHz, CDCl 3 ), δ (TMS, ppm): 8.51 - 8.48 (s, 1H), 8.33 - 8.31 (d, 1H), 7.97 - 7.93 (d, 1H), 7.53 - 7.51 (d, 1H), 7.39 - 7.36 (d, 2H), 7.05 - 6.97 (m, 3H), 6.80 (s, 1H), 4.03 (s, 1H), 1.35 (m, 9H).

[0132] (4) Add 1 mmol of the third intermediate product, 1 mmol of the fifth reactant, 0.05 mmol of tetrakis(triphenylphosphine)palladium, and 3 mmol of sodium carbonate to a 100 mL two-necked flask in sequence. Add a magnetic stirring bar, perform vacuum evacuation and nitrogen replacement operations to make the reaction flask under a nitrogen atmosphere. Add 50 mL of a mixed solvent of tetrahydrofuran / deionized water (V / V = 3:1), and reflux the reaction at 70 °C for 24 h; cool to room temperature, place the above reaction solution in dichloromethane, extract with water multiple times, and then use anhydrous MgSO 4 dry, filter, rotary evaporate to remove the solvent in the above mixture, use ethanol, ethyl acetate, and petroleum ether as the eluent, rotary evaporate to remove the eluent, then dissolve the solid obtained by rotary evaporation in chlorobenzene, filter, and rotary evaporate to remove the solvent in the filtrate to obtain a hole functional material (hereinafter referred to as T3). Among them, the reaction formula for the fifth reactant and the third intermediate product to react to form the hole functional material is:

[0133]

[0134] In this example, the yield of the hole functional material T3 is 69%. The number-average molecular weight Mn of T3 is 38794 g / mol. The dispersity index PDI of T3 is 1.95.

[0135] Example 4

[0136] The difference between this example and Example 1 lies in that the structural formula of the fifth reactant and step (4) are different. Among them, the fifth reactant in this example is Step (4) is specifically as follows:

[0137] (4) Add 1 mmol of the third intermediate product, 1 mmol of the fifth reactant, 0.05 mmol of tetrakis(triphenylphosphine)palladium, and 3 mmol of sodium carbonate into a 100 mL two-necked flask in sequence. Add a magnetic stir bar, perform a vacuum nitrogen replacement operation to make the inside of the reaction flask in a nitrogen atmosphere. Add 50 mL of a mixed solvent of tetrahydrofuran / deionized water (V / V = 3:1), and reflux and react at 70 °C for 24 h; cool to room temperature, place the above reaction solution in dichloromethane, extract with water multiple times, and then use anhydrous MgSO 4 Dry, filter, rotary evaporate to remove the solvent in the above mixed solution, use ethanol, ethyl acetate, and petroleum ether as eluents, rotary evaporate to remove the eluents, then dissolve the solid obtained by rotary evaporation in chlorobenzene, filter, and rotary evaporate to remove the solvent in the filtrate to obtain a hole functional material (hereinafter referred to as T4). Among them, the reaction formula for the fifth reactant and the third intermediate product to react to form a hole functional material is:

[0138]

[0139] In this example, the yield of the hole functional material T4 is 56%. The number average molecular weight Mn of T4 is 18794 g / mol. The dispersity index PDI of T4 is 1.73.

[0140] Example 5

[0141] The difference between this example and Example 1 lies in that the structural formula of the fifth reactant and step (4) are different. Among them, the fifth reactant in this example is Step (4) is specifically as follows:

[0142] (4) Add 1 mmol of the third intermediate product, 1 mmol of the fifth reactant, 0.05 mmol of tetrakis(triphenylphosphine)palladium, and 3 mmol of sodium carbonate into a 100 mL two-necked flask in sequence. Add a magnetic stir bar, perform a vacuum nitrogen replacement operation to make the inside of the reaction flask in a nitrogen atmosphere. Add 50 mL of a mixed solvent of tetrahydrofuran / deionized water (V / V = 3:1), and reflux and react at 70 °C for 24 h; cool to room temperature, place the above reaction solution in dichloromethane, extract with water multiple times, and then use anhydrous MgSO 4Dry, filter, and rotary evaporate to remove the solvent from the above-mentioned mixed solution. Use ethanol, ethyl acetate, and petroleum ether as eluents, rotary evaporate to remove the eluents, and then dissolve the solid obtained by rotary evaporation in chlorobenzene, filter, and rotary evaporate to remove the solvent from the filtrate to obtain the hole-functional material. (hereinafter referred to as T5). Among them, the reaction formula for the fifth reactant and the third intermediate to react to form the hole-functional material is:

[0143]

[0144] In this example, the yield of the hole-functional material T5 is 56%. The number-average molecular weight Mn of T5 is 22178 g / mol. The dispersity index PDI of T5 is 1.67.

[0145] Example 6

[0146] The difference between this example and Example 1 is that this example further includes a sixth reactant, and the structural formula of the fifth reactant and step (4) are different. Among them, the fifth reactant in this example is The sixth reactant is Step (4) is specifically as follows:

[0147] (4) Add 1 mmol of the third intermediate, 0.5 mmol of the fifth reactant, 0.5 mmol of the sixth reactant, 0.05 mmol of tetrakis(triphenylphosphine)palladium, and 3 mmol of sodium carbonate to a 100 mL two-necked flask in sequence. Add a magnetic stirrer, perform vacuum replacement with nitrogen to make the reaction flask under a nitrogen atmosphere, add 50 mL of a mixed solvent of tetrahydrofuran / deionized water (V / V = 3:1), and reflux and react at 70 °C for 24 h; cool to room temperature, place the above reaction solution in dichloromethane, extract with water multiple times, and then use anhydrous MgSO 4 Dry, filter, and rotary evaporate to remove the solvent from the above-mentioned mixed solution. Use ethanol, ethyl acetate, and petroleum ether as eluents, rotary evaporate to remove the eluents, and then dissolve the solid obtained by rotary evaporation in chlorobenzene, filter, and rotary evaporate to remove the solvent from the filtrate to obtain the hole-functional material (hereinafter referred to as T6). Among them, the reaction formula for the fifth reactant and the sixth reactant to react to form the hole-functional material is:

[0148] In this example, the yield of the hole-functional material T6 is 49%. The number-average molecular weight Mn of T6 is 10173 g / mol. The dispersity index PDI of T6 is 2.67.

[0149] An embodiment of the present application further provides a mixture, which comprises an organic compound and at least one organic functional material. The organic compound may be the organic compound described in the foregoing embodiments, and the structural formula of the organic compound may refer to the description in the foregoing embodiments, which will not be elaborated herein. The organic functional material is selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a light-emitting material, a host material or an organic dye.

[0150] Among them, the hole injection material may be an organic material such as 3,4-ethylenedioxythiophene: poly(styrenesulfonate) (PEDOT:PSS), or may be an inorganic material such as nickel oxide (NiOx), tungsten trioxide (WO 3 ) or molybdenum trioxide (MoO 3 ).

[0151] The hole transport material may be an organic material, such as may include one or more of poly(9,9-dioctylfluorene-co-N-(4-butylphenyl)diphenylamine) (TFB), polyvinylcarbazole (PVK), poly(N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine) (poly-TPD), poly(9,9-dioctylfluorene-co-bis-N,N-phenyl-1,4-phenylenediamine) (PFB), 4,4',4''-tris(carbazol-9-yl)triphenylamine (TCTA), 4,4'-bis(9-carbazolyl)biphenyl (CBP), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD) and N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB); the hole transport material may also be an inorganic material, such as may include copper oxide (Cu 2 O) or copper gallium oxide nanoparticles (CuxGa1-xO).

[0152] The electron transport material may include one or more of aluminum 8-hydroxyquinolate, 4,7-diphenyl-1,10-phenanthroline, 1,3,5-tris(1-phenyl-1H-benzoimidazol-2-yl)benzene, 2-(4'-tert-butylphenyl)-5-(4'-biphenylyl)-1,3,4-oxadiazole, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole, 4,4'-bis(2,2-distyryl)-1,1'-biphenyl, 2,5-bis(5-tert-butyl-2-benzoxazolyl)thiophene, zinc 8-hydroxyquinolate, gallium 8-hydroxyquinolate, beryllium bis(10-hydroxybenzo[h]quinolinato), bis(2-methyl-8-hydroxyquinolinato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum, ZnSPB, 2-(4-biphenylyl)-5-phenyloxadiazole, 72,2'-(1,3-phenylene)bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazole].

[0153] The electron injection material is one or more of poly[(9,9-bis(3'-(N,N-dimethylamino)propyl)fluorene-2,7-diyl)-ALT-[(9,9-dioctylfluorene-2,7-diyl)-bromo(PFN-Br)] and poly[(9,9-bis(3'-(N,N-dimethylamino)propyl)-2,7-fluorene)-2,7-(9,9-dioctylfluorene)] (PFN-DOF).

[0154] The electron blocking material includes one or more of polyvinylcarbazole (PVK), poly(N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine) (poly-TPD), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (NPB), 4,4',4''-tris(carbazol-9-yl)triphenylamine (TCTA), and 4,4'-bis(9-carbazolyl)biphenyl (CBP).

[0155] The hole blocking material may include carbon nanotube-doped polymethyl methacrylate (PMMA) or nano-aluminum oxide-doped PMMA.

[0156] The light-emitting material may include DCM, DCT, DPP, MQA, DCJT, DCJTB, DCJTI, BPVBi, DMQA, TMDBQA, TPBD, PAAA, TAZ, RD 3 , PtOEP, Ir(BPPa) 3 , Ir(piq) 3 , Ir(BPPya) 3 , Ir(ppy) 3 , Ir(btpy)3 , FCNIr, FIrN 4 , FIrPic, OXD-(P-NMe2), BPVBi, PPV, MEH-PPV, PPP, Zn(BTZ) 2 , Be(PP) 2 , DPAVBi, DPAVB and FIr 6 or more of the above.

[0157] The host material is used to be doped with the luminescent material to form a luminescent layer, so as to form a stable luminescent layer morphology. Among them, the host material may include mCP or TPBi.

[0158] The organic dye may include at least one of coumarin compounds, quinoxaline derivatives, and anthranilic acid amide derivatives.

[0159] An embodiment of the present application provides a composition, which includes an organic compound or a mixture, and at least one organic solvent. Among them, the organic compound may be the organic compound described in the foregoing embodiments, and the structural formula of the organic compound may refer to the description of the foregoing embodiments, which will not be elaborated here. The mixture may be the mixture described in the foregoing embodiments, and the composition of the mixture may refer to the description of the foregoing embodiments, which will not be elaborated here.

[0160] Among them, the organic solvent is used to dissolve the organic compound or the mixture. The organic solvent may include one or more of chlorobenzene, dichlorobenzene, methanol, ethanol, propanol, butanol, butane, pentane, hexane, heptane, and octane. The organic solvent can be specifically selected according to the type of the organic compound, which will not be elaborated here.

[0161] An embodiment of the present application further provides a semiconductor device, which includes a first electrode, a second electrode, and one or more functional layers located between the first electrode and the second electrode.

[0162] Among them, the first electrode may be a cathode. The second electrode may be an anode. It should be noted that the functional layer may be a hole functional layer or an electron functional layer, etc. In this embodiment, only the case where the functional layer is a hole functional layer is taken as an example for illustration, but it is not limited thereto.

[0163] In some embodiments, the hole functional layer includes an organic compound. The structural formula of the organic compound is one of the following. The 1 structural formula of the A is one of the following. The A 2 group, the A 11 group, and the A12 The structural formulas of the groups are each independently selected from one of them. The A 2 group is different from the A 1 group. The A 11 group is different from the A 12 group. The R group is a hydrogen atom or an alkyl group. n > 1 and is an integer. 0 < m < 1.

[0164] In some embodiments, the structural formula of the organic compound is one of them.

[0165] As Figure 3 shown, in this embodiment, the semiconductor device 100 includes a substrate layer 10, a hole injection layer 11, a hole functional layer 12, a light-emitting layer 13, an electron transport layer 14, and a first electrode 15 arranged in sequence. Among them, the substrate layer 10 includes a substrate 101 and a second electrode 102. The second electrode 102 is located on the side of the substrate 101 close to the hole injection layer 11.

[0166] It should be noted that, in this embodiment, the hole functional layer 12 refers to a hole transport layer. In some embodiments, the hole functional layer 12 may also refer to a hole injection layer, and this embodiment should not be construed as a limitation to the present application. Additionally, in some embodiments, the semiconductor device 100 may further include functional layers such as an electron blocking layer and a hole blocking layer, which will not be elaborated herein.

[0167] In some embodiments, the thickness of the hole injection layer 11 may be 10 nm - 50 nm. The thickness of the hole functional layer 12 may be 20 nm - 60 nm. The thickness of the light-emitting layer 13 may be 20 nm - 60 nm. The thickness of the electron transport layer 14 may be 20 nm - 60 nm. The thickness of the first electrode 15 may be 80 nm - 120 nm.

[0168] It should be noted that the semiconductor device 100 in the present application may be an OLED device or a QLED device. This embodiment only takes the semiconductor device 100 as a QLED device as an example for illustration, but is not limited thereto.

[0169] In some embodiments, the hole functional layer 12 comprises a mixture. The mixture may be the mixture described in the foregoing embodiments and will not be elaborated herein.

[0170] In some embodiments, the hole functional layer 12 is prepared from a composition. The composition may be the composition described in the foregoing embodiments and will not be elaborated herein.

[0171] This application provides Examples (1)-(6), and semiconductor devices 1 (corresponding to Example (1), hereinafter denoted as "T1 device"), semiconductor devices 2 (corresponding to Example (2), hereinafter denoted as "T2 device"), semiconductor devices 3 (corresponding to Example (3), hereinafter denoted as "T3 device"), semiconductor devices 4 (corresponding to Example (4), hereinafter denoted as "T4 device"), semiconductor devices 5 (corresponding to Example (5), hereinafter denoted as "T5 device"), and semiconductor devices 6 (corresponding to Example (6), hereinafter denoted as "T6 device") are respectively fabricated according to methods known in the art. Among them, in the above embodiments, the organic compound is a hole transport material.

[0172] Among them, in the T1 device - T6 device, the thicknesses of the second electrode 102, the hole injection layer 11, the hole functional layer 12, the light-emitting layer 13, and the first electrode 15, as well as the materials used for each film layer, are the same. Specifically, the material of the second electrode 102 is indium tin oxide, and the thickness is 40 nm. The material of the hole injection layer 11 is poly(3,4-ethylenedioxythiophene) (PEDOT): poly(styrenesulfonate) (PSS), and the thickness is 20 nm. The material of the light-emitting layer 13 is red quantum dots, and the thickness is 20 nm. The material of the electron transport layer 14 is zinc oxide, and the thickness is 50 nm. The material of the first electrode 15 is aluminum, and the thickness is 120 nm.

[0173] The thicknesses of the hole functional layer 12 in the T1 device - T6 device are the same, all being 30 nm. The difference among the T1 device - T6 device is only that the hole functional materials used for the hole functional layer 12 are different. Among them, the hole functional material used for the hole functional layer 12 of the T1 device is The hole functional material used for the hole functional layer 12 of the T2 device is The hole functional material used for the hole functional layer 12 of the T3 device is The hole functional material used for the hole functional layer 12 of the T4 device is The hole functional material used for the hole functional layer 12 of the T5 device is The hole functional material used for the hole functional layer 12 of the T6 device is

[0174] It should be noted that the hole functional materials used in the T1 device - T6 device are respectively prepared through Examples 1 - 6 in the aforementioned preparation method of the hole functional material, and will not be elaborated here.

[0175] This application also provides a comparative example. The difference from the above - mentioned Examples (1) - (6) is that in the semiconductor device of the comparative example, the hole functional material used in the hole functional layer 12 is poly(9,9 - dioctylfluorene - co - N-(4 - butylphenyl)diphenylamine) (TFB), and the semiconductor device of the comparative example is denoted as "S1 device".

[0176] Through experimental measurement, the current density, voltage, current efficiency, and color coordinates of the S1 device, T1 device - T6 device are obtained at the same brightness (1000 cd / m 2 ). Figure 1 is the curve graph between the current density and voltage of the S1 device and T1 device - T6 device, Figure 2 is the curve graph between the current efficiency and current density of the S1 device and T1 device - T6 device. Table 1 shows the current efficiency of the S1 device and T1 device - T6 device at their respective corresponding color coordinates.

[0177] Table 1

[0178]

[0179]

[0180] Through comparative analysis, it can be known that the T1 device - T6 device prepared with the hole functional material of this application has a higher current efficiency. Since the synthesis route of the hole functional material provided by this application is simple, therefore, by using the hole functional material of this application to prepare semiconductor devices, not only can the high efficiency of the devices be achieved, but also the manufacturing cost of the devices can be reduced.

[0181] Compared with the organic compounds in the prior art, this application generates a first intermediate product by using a first reactant and a second reactant, a second intermediate product by using a third reactant and the first intermediate product, a third intermediate product by using a fourth reactant and the second intermediate product, and an organic compound by using a fifth reactant and the third intermediate product, and replaces the covalent bond in the fluorene unit in the prior art with a hydrogen bond formed by the hydrogen in the amino group and the lone pair electrons on the nitrogen atom, realizing a preparation process of a polymer - type material with a simple synthesis route.

[0182] The above has introduced in detail an organic compound, its preparation method, mixture, composition and semiconductor device provided by the embodiments of the present application. Specific examples are used in this article to elaborate on the principle and implementation manner of the present application. The description of the above embodiments is only used to help understand the method and its core idea of the present application; at the same time, for those skilled in the art, according to the idea of the present application, there will be changes in the specific implementation manner and application scope. In summary, the content of this specification should not be construed as a limitation to the present application.

Claims

1. An organic compound, characterized in that, The structural formula of the organic compound is one of the following, where the A 1 group has a structural formula of One of the following, the A 2 group, the A 11 group and the A 12 group structural formulas are each independently selected from one of; Among them, the A 2 group is different from the A 1 group, the A 11 group and the A 12 group are different, the R group is a hydrogen atom or an alkyl group, n > 1 and is an integer, 0 < m < 1.

2. The organic compound according to claim 1, characterized in that, the structural formula of the organic compound is one of 3. The organic compound according to claim 1, characterized in that, the chemical formula of the organic compound is One of 4. A method for preparing an organic compound, characterized in that, comprising the following steps: Provide a first reactant and a second reactant, where the first reactant and the second reactant react to form a first intermediate product. Among them, the structural formula of the first reactant is One of them, and the structural formula of the second reactant is One of them, and the X group is a halogen; A third reactant is provided, and the third reactant reacts with the first intermediate product to generate a second intermediate product, wherein the third reactant is a compound containing an amino group or an anilino group, and the structural formula of the third reactant is R-NH 2 or the R group is a hydrogen atom or an alkyl group; providing a fourth reactant, and reacting the fourth reactant with the second intermediate to form a third intermediate, wherein the fourth reactant is liquid bromine; Provide a fifth reactant, which reacts with the third intermediate to form an organic compound, wherein the structural formula of the fifth reactant is one of the following, and the A 2 chemical formula of the group is One of the following, said A 2 group and said A 1 groups are different, and the structural formula of the organic compound is n > 1 and is an integer; or Provide a fifth reactant and a sixth reactant, wherein the fifth reactant, the sixth reactant and the third intermediate react to form an organic compound. Among them, the structural formula of the fifth reactant is The structural formula of the sixth reactant The A 11 group and the A 12 groups are independently selected from One of the following, said A 11 group and said A 12 groups are different, and the structural formula of the organic compound is 0 < m < 1.

5. The method for preparing an organic compound according to claim 4, the structural formula of the organic compound is one of 6. The method for preparing an organic compound according to claim 4, characterized in that, The chemical formula of the organic compound is one of 7. The method for preparing an organic compound according to claim 4, characterized in that, in the reaction of the first reactant and the second reactant to form the first intermediate, the corresponding relationship between the molar amount of the first reactant and the molar amount of the second reactant is that 20 mmol of the first reactant corresponds to 5 mmol - 15 mmol of the second reactant; and / or in the reaction of the third reactant and the first intermediate to form the second intermediate, the corresponding relationship between the molar amount of the third reactant and the molar amount of the first intermediate is that 25 mmol of the third reactant corresponds to 5 mmol - 15 mmol of the first intermediate.

8. The method for preparing an organic compound according to claim 4, characterized in that, in the reaction of the fourth reactant and the second intermediate to form the third intermediate, the corresponding relationship between the molar amount of the fourth reactant and the molar amount of the second intermediate is that 30 mmol of the fourth reactant corresponds to 1 mmol - 20 mmol of the second intermediate.

9. The method for preparing an organic compound according to claim 4, characterized in that, in the reaction of the fifth reactant and the third intermediate to form the organic compound, the corresponding relationship between the molar amount of the fifth reactant and the molar amount of the third intermediate is that 18 mmol of the fifth reactant corresponds to 1 mmol - 15 mmol of the third intermediate; or in the reaction of the fifth reactant, the sixth reactant and the third intermediate to form the organic compound, the corresponding relationship between the molar amount of the fifth reactant, the sixth reactant and the molar amount of the third intermediate is that 1 - 20 mmol of the fifth reactant, 1 - 20 mmol of the sixth reactant corresponds to 25 mmol of the third intermediate.

10. A mixture, characterized in that, comprising the organic compound according to any one of claims 1 - 3, and at least one organic functional material, wherein the organic functional material is selected from a hole injection material, a hole transport material, an electron transport material, an electron injection material, an electron blocking material, a hole blocking material, a light emitting material or a host material, and wherein the light emitting material includes an organic dye.

11. A composition, characterized in that, Comprising an organic compound as described in any one of claims 1-3 or the mixture as described in claim 10, and at least one organic solvent.

12. A semiconductor device, characterized in that the semiconductor device includes a first electrode, a second electrode, and one or more functional layers located between the first electrode and the second electrode, and the functional layer includes an organic compound as described in any one of claims 1 to 3, or the mixture as described in claim 10, or is prepared from the composition as described in claim 11.

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