Organic compound, preparation method thereof, mixture, composition and semiconductor device

Abstract

The present application discloses an organic compound and a preparation method, mixture, composition and semiconductor device thereof. The organic compound is generated 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 the organic compound. The hydrogen bond formed by the hydrogen in the amine group and the lone pair of electrons on the nitrogen atom replaces the covalent bond in the fluorene unit in the prior art, thereby realizing a preparation process for a small molecule material with a simple synthetic route.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) offer advantages such as fast response, high contrast, wide viewing angles, and flexibility. With the continuous advancement of display technology, OLED's yield rate and production costs have been effectively controlled, and its market share is gradually increasing. Quantum dot light-emitting diodes (QLEDs), very similar to OLEDs, also offer fast response, high contrast, wide viewing angles, flexibility, and a wider color gamut.

[0003] In the film structures of OLED and QLED devices, the hole transport layer plays a crucial role by significantly reducing the hole transport energy barrier, lowering device voltage, and improving device efficiency. In existing technologies, polyfluorene-based polymers are commonly used as hole transport materials, but the synthesis route for fluorene is complex. Summary of the Invention

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

[0005] The present invention provides an organic compound with a structural formula of D-A1-H or D1-A1-D2, wherein the structural formula of the A1 group is In one of the above, the structural formulas of the D group, the D1 group and the D2 group are independently selected from One of the following;

[0006] Wherein, the R group is a hydrogen atom or an alkyl group.

[0007] Optionally, in some embodiments of the present application, the structural formulas of the D1 group and the D2 group are the same.

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

[0009] The present invention provides a method for preparing an organic compound, which comprises the following steps:

[0010] A first reactant and a second reactant are provided, wherein the first reactant and the second reactant react to form a first intermediate product, wherein the structural formula of the first reactant is In one of the above, the structural formula of the second reactant is In one of the above, the X group is a halogen;

[0011] Providing a third reactant, wherein the third reactant reacts with the first intermediate product to generate a second intermediate product, wherein the third reactant is a compound containing an amine group or an aniline group, and the R group is a hydrogen atom or an alkyl group;

[0012] Providing a fourth reactant, wherein the fourth reactant reacts with the second intermediate product to generate a third intermediate product, wherein the fourth reactant is liquid bromine;

[0013] Providing a fifth reactant, the fifth reactant and the third intermediate product react to form an organic compound, wherein the structural formula of the fifth reactant is The structural formula of the D group is One of the above, the structural formula of the organic compound is D-A1-H or D1-A1-D2, and the structural formula of the A1 group is In one of the above, the structural formulas of the D1 group and the D2 group are independently selected from One of them.

[0014] Optionally, in some embodiments of the present application, the structural formula of the organic compound is One of them.

[0015] Optionally, in some embodiments of the present application, in the reaction between the first reactant and the second reactant to generate the first intermediate product, the corresponding relationship between the molar amount of the first reactant and the molar amount of the second reactant is 20 mmol of the first reactant corresponds to 5 mmol-15 mmol of the second reactant; and / or

[0016] When the third reactant and the first intermediate product react to generate 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.

[0017] Optionally, in some embodiments of the present application, when the fourth reactant and the second intermediate product react to generate the third intermediate product, the corresponding relationship between the molar amount of the fourth reactant and the molar amount of the second intermediate product is 30 mmol of the fourth reactant corresponds to 1 mmol-20 mmol of the second intermediate product; and / or

[0018] When the fifth reactant and the third intermediate product react to generate the organic compound, the corresponding relationship between the molar amount of the fifth reactant and the molar amount of the third intermediate product is that 20 mmol of the fifth reactant corresponds to 1 mmol-15 mmol of the third intermediate product.

[0019] An embodiment of the present application also provides a mixture, which comprises an organic compound as described in any of the preceding embodiments, 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 luminescent material, a host material or an organic dye.

[0020] The present application also provides a composition comprising the organic compound or the mixture as described in any of the above embodiments, and at least one organic solvent.

[0021] An embodiment of the present application also 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, wherein the functional layer includes the organic compound described in any of the foregoing embodiments, or the mixture described in the foregoing embodiments, or is prepared from the composition described in the foregoing embodiments.

[0022] The present application provides an organic compound and a preparation method, mixture, composition and semiconductor device thereof. The organic compound is generated 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. The hydrogen bond formed by the hydrogen in the amine group and the lone pair of electrons on the nitrogen atom replaces the covalent bond in the fluorene unit in the prior art, thereby realizing a preparation process for small molecule materials with a simple synthetic route. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for use in the description of the embodiments. Obviously, the drawings described below 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 work.

[0024] Figure 1 is a graph showing the current density and voltage of the R1 device and the T1 device to the T4 device in this application.

[0025] Figure 2 Graphs showing the current efficiency and current density of the R1 device and the T1-T4 devices in this application.

[0026] Figure 3 It is a structural schematic diagram of the semiconductor device provided by this application. DETAILED DESCRIPTION

[0027] The technical solutions in the embodiments of the present application will be clearly and completely described below in conjunction with the drawings in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without making creative work are within the scope of protection of the present application. In addition, it should be understood that the specific implementation methods described herein are only used to illustrate and explain the present application, and are not used to limit the present application. In the present application, unless otherwise specified, the directional words used, such as "up", "down", "left" and "right", generally refer to the up, down, left and right of the device in actual use or working state, specifically the direction of the drawing in the accompanying drawings; and "inside" and "outside" refer to the outline of the device.

[0028] The present application provides an organic compound, a preparation method thereof, a mixture, a composition, and a semiconductor device. These are described in detail below. It should be noted that the order in which the following embodiments are described does not limit the preferred order of the embodiments.

[0029] It should be noted that the organic compounds in this application can be used as hole injection materials to prepare hole injection layers; the organic compounds in this application can also be used as hole transport materials to prepare hole transport layers. The application scenarios of the organic compounds can be selected according to actual application requirements and are not limited in this application.

[0030] It is understood that in this application, the “*” in all structural formulas refers to a connection site for forming a chemical bond with other groups.

[0031] The present application provides an organic compound having a structural formula of D-A1-H or D1-A1-D2. The structural formula of the A1 group is The structural formulas of the D group, the D1 group and the D2 group are independently selected from The R group is a hydrogen atom or an alkyl group.

[0032] When the R group is an alkyl group, the number of carbon atoms in the alkyl group is between 1 and 18.

[0033] In some embodiments of the present application, the structural formulas of the D1 group and the D2 group may be the same, thereby increasing the yield of the organic compound and simplifying the synthesis route.

[0034] In some embodiments of the present application, the structural formulas of the D1 group and the D2 group may also be different.

[0035] In some embodiments of the present application, the structural formula of the organic compound can be

[0036] etc.

[0037] The present application provides a method for preparing an organic compound, which comprises the following steps:

[0038] B1: Provide a first reactant and a second reactant, wherein the first reactant and the second reactant react to form a first intermediate product, wherein the structural formula of the first reactant is In one of the above, the structural formula of the second reactant is One of the above, wherein the structural formula of the first intermediate product is In one of the above, the X group is halogen.

[0039] In some embodiments, the X group can be a Br atom, a Cl atom, or an I atom.

[0040] In some embodiments, when the structural formula of the first reactant is The structural formula of the second reactant is When the first reactant and the second reactant react to form the first intermediate product, the general reaction formula is:

[0041]

[0042] In some embodiments, when the structural formula of the first reactant is The structural formula of the second reactant is When the first reactant and the second reactant react to form the first intermediate product, the general reaction formula is:

[0043]

[0044] In some embodiments, when the structural formula of the first reactant is The structural formula of the second reactant is When the first reactant and the second reactant react to form the first intermediate product, the general reaction formula is:

[0045]

[0046] In some embodiments, when the structural formula of the first reactant is The structural formula of the second reactant is When the first reactant and the second reactant react to form the first intermediate product, the general reaction formula is:

[0047]

[0048] 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 mixture is heated under reflux under a nitrogen atmosphere to react to obtain a mixture including a first intermediate product, and the mixture is separated and purified to obtain the first intermediate product.

[0049] In some embodiments, in the reaction between the first reactant and the second reactant to generate the first intermediate product, the corresponding relationship between the molar amount of the first reactant and the molar amount of the second reactant is 20 mmol of the first reactant corresponding 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 20 mmol of the first reactant corresponding 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 20 mmol of the first reactant corresponding to 5 mmol of the second reactant.

[0050] In some embodiments, the first reactant and the second reactant react in a first solvent to produce the first intermediate product. The first solvent comprises one or a combination of water, acetone, n-butanol, ethyl formate, methyl acetate, peroxypropionic acid, peracetic acid, ether, chloroform, tetrahydrofuran, acetic acid, formic acid, formaldehyde, hydroxypropionic acid, thioglycolic acid, indole-3-acetic acid, methyl formate, and 2-hydroxyacetaldehyde.

[0051] 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.

[0052] In some embodiments, the first solvent contains the first additive, which includes one or a combination of sodium carbonate, potassium carbonate, tetrakistriphenylphosphine palladium, n-butyl lithium, potassium hydroxide, sodium hydroxide, and sodium tert-butoxide.

[0053] In some embodiments, during the reaction of the first reactant and the second reactant to form the first intermediate product, the reaction temperature is 50° C. to 150° C., such as 50° C., 60° C., 70° C., 80° C., 90° C., 100° C., 120° C., or 150° C. The reaction time is 12 h to 36 h, such as 12 h, 15 h, 18 h, 20 h, 24 h, 30 h, 32 h, or 36 h.

[0054] B2: providing a third reactant, the third reactant reacting with the first intermediate product to generate a second intermediate product, wherein the third reactant is a compound containing an amine group or an aniline group, the second intermediate product is a compound containing an A1 group, and the structural formula of the second intermediate product is One of the following, wherein the structural formula of the A1 group is

[0055] In one of the above, 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 third reactant has a structural formula of 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, a second additive and a second solvent are added to react, the mixture is heated under reflux under a nitrogen atmosphere to react, and a mixture including the second intermediate product is obtained, and the mixture is separated and purified to obtain the second intermediate product.

[0059] In some embodiments, when the third reactant and the first intermediate product react 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 25 mmol of the third reactant corresponding 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 12 mmol of the third reactant corresponding 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 24 mmol of the third reactant corresponding to 10 mmol of the first intermediate product.

[0060] In some embodiments, the third reactant and the first intermediate product react in a second solvent to produce the second intermediate product. The second solvent comprises one or a combination of ethylene dichloride, isopropyl ether, butyl acetate, ethyl 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.

[0062] In some embodiments, the second solvent contains the second additive, which includes one or a combination of sodium carbonate, potassium carbonate, potassium hydroxide, sodium hydroxide, and sodium tert-butoxide.

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

[0064] B3: Providing a fourth reactant, the fourth reactant reacts with the second intermediate product to generate a third intermediate product, wherein the fourth reactant is liquid bromine, and the structural formula of the third intermediate product is Br-A1-H or Br-A1-Br.

[0065] In some embodiments, the fourth reactant and the second intermediate product are added to a two-necked flask, a third additive and a third solvent are added to react, and the mixture is heated under reflux under a nitrogen atmosphere to react to obtain a mixture including the third intermediate product, and the mixture is separated and purified to generate the third intermediate product.

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

[0067] In some embodiments, the fourth reactant and the second intermediate product react in the third solvent to produce the third intermediate product. The third solvent comprises one or a combination of ethylene dichloride, isopropyl ether, butyl acetate, ethyl 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.

[0069] In some embodiments, the third solvent contains the third additive, which includes one or a combination of sodium methoxide, sodium ethoxide, ferric bromide, and ferrous bromide.

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

[0071] B4: Providing a fifth reactant, wherein the fifth reactant reacts with the third intermediate product to generate an organic compound, wherein the structural formula of the fifth reactant is The structural formula of the D group is The structural formula of the organic compound is D-A1-H or D1-A1-D2, and the structural formulas of the D1 group and the D2 group are independently selected from One of them.

[0072] In some embodiments, when the structural formula of the third intermediate product is Br-A1-H, the general reaction formula for the reaction between the fifth reactant and the third intermediate product to generate an organic compound is:

[0073]

[0074] In some embodiments, the structural formula of the organic compound can be etc.

[0075] In some embodiments, when the structural formula of the third intermediate product is Br-A1-Br, the general reaction formula for the reaction between the fifth reactant and the third intermediate product to generate an organic compound is:

[0076] or

[0077]

[0078] In some embodiments, the structural formula of the organic compound can be etc.

[0079] In some embodiments, the fifth reactant and the third intermediate product are added to a two-necked flask, a fourth additive and a fourth solvent are added to react, and the mixture is heated under reflux under a nitrogen atmosphere to react to obtain a mixture including an organic compound, and the mixture is separated and purified to obtain the organic compound.

[0080] In some embodiments, when the fifth reactant and the third intermediate product react to form the organic compound, the corresponding relationship between the molar amount of the fifth reactant and the molar amount of the third intermediate product is 20 mmol of the fifth reactant corresponding to 1 mmol-15 mmol of the third intermediate product. Specifically, the corresponding relationship between the molar amount of the fifth reactant and the molar amount of the third intermediate product can be 20 mmol of the fifth reactant corresponding to 7 mmol of the third intermediate product. The corresponding relationship between the molar amount of the fifth reactant and the molar amount of the third intermediate product can also be 20 mmol of the fifth reactant corresponding to 12 mmol of the third intermediate product.

[0081] In some embodiments, the fifth reactant and the third intermediate product react in a fourth solvent to produce the organic compound. The fourth solvent comprises one or a combination of water, acetone, n-butanol, ethyl formate, methyl acetate, peroxypropionic acid, peracetic acid, ether, chloroform, tetrahydrofuran, acetic acid, formic acid, formaldehyde, hydroxypropionic acid, thioglycolic acid, indole-3-acetic acid, toluene, 1-methyl-2-pyrrolidone, methyl formate, and 2-hydroxyacetaldehyde.

[0082] 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.

[0083] In some embodiments, the fourth solvent contains the fourth additive, which includes one or a combination of sodium carbonate, potassium carbonate, tetrakistriphenylphosphine palladium, copper oxide, n-butyl lithium, potassium hydroxide, sodium hydroxide, and sodium tert-butoxide.

[0084] In some embodiments, during the reaction of the fifth reactant and the third intermediate product to form the organic compound, the reaction temperature is 50° C. to 300° C., such as 50° C., 60° C., 70° C., 80° C., 100° C., 120° C., 150° C., 180° C., 200° C., 240° C., 275° C., or 300° C. The reaction time is 12 h to 72 h, such as 12 h, 15 h, 18 h, 20 h, 24 h, 30 h, 32 h, 36 h, 48 h, 52 h, 64 h, or 72 h.

[0085] The following examples further illustrate the preparation method of the organic compound provided by the present application. In the following examples, the organic compound is a hole transport material.

[0086] Example 1

[0087] In this embodiment, the first reactant is The second reactant is The third reactant is C4H9NH2, the fourth reactant is liquid bromine Br2, and the fifth reactant is

[0088] (1) 2 mmol of the first reactant, 1 mmol of the second reactant, 0.05 mmol of tetrakistriphenylphosphine palladium and 3 mmol of sodium carbonate were added to a 100 mL two-necked flask in sequence, a magnetic stirring bar was added, and a vacuum-exchanged nitrogen operation was performed to place the reaction flask in a nitrogen atmosphere; 50 mL of a mixed solvent of tetrahydrofuran / deionized water (V / V=3:1) was added, and the mixture was refluxed at 70°C for 24 h; the mixture was cooled to room temperature, and the reaction solution was placed in dichloromethane, extracted with water several times, and then dried with anhydrous MgSO4, filtered, and the solvent in the mixed solution was removed by rotary evaporation. Hexane / dichloromethane was used as an eluent, and the eluent was removed by rotary evaporation to obtain the first intermediate product. The reaction formula for the first reactant and the second reactant to generate the first intermediate product is:

[0089]

[0090] In this embodiment, the first intermediate product The yield was 66%. 1H NMR (500 MHz, CDCl3), 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).

[0091] (2) 1.2 mmol of the third reactant, 1.0 mmol of the first intermediate product and 1.5 mmol of potassium carbonate were added to a 100 mL two-necked flask in sequence, a magnetic stirring bar was added, and a vacuum-exchanged nitrogen operation was performed to place the reaction flask in a nitrogen atmosphere; 50 mL of acetone was added, and the reaction was refluxed at 50° C. for 12 h; the reaction solution was cooled to room temperature, and the reaction solution was placed in dichloromethane, extracted with water several times, and the organic phase was taken, and then dried with anhydrous MgSO4, filtered, and the solvent in the mixed solution was removed by rotary evaporation. Hexane / dichloromethane was used as an eluent, and the eluent was removed by rotary evaporation to obtain the second intermediate product. The reaction formula for the third reactant and the first intermediate product to generate the second intermediate product is:

[0092]

[0093] In this embodiment, the second intermediate product The yield was 83%. 1H NMR (500 MHz, CDCl3), 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).

[0094] (3) 1 mmol of the second intermediate product and 0.05 mmol of ferric bromide were added to a 100 mL two-necked flask in sequence, a magnetic stirring rod was added, and a vacuum-exchanged nitrogen operation was performed to place the reaction flask in 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 reaction solution was extracted with water several times, and the organic phase was taken, then dried with anhydrous MgSO 4 , filtered, and the solvent in the mixed solution was removed by rotary evaporation. Hexane / dichloromethane was used as an eluent, and the eluent was removed by rotary evaporation to obtain the third intermediate product. The reaction formula for the fourth reactant and the second intermediate product to generate the third intermediate product is:

[0095]

[0096] In this embodiment, the third intermediate product The yield was 63%. 1H NMR (500 MHz, CDCl3), 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).

[0097] (4) 1 mmol of the third intermediate product, 3 mmol of the fifth reactant, 0.05 mmol of tetrakistriphenylphosphine palladium and 3 mmol of sodium carbonate were added to a 100 mL two-necked flask in sequence, a stirring magnet was added, and a vacuum-exchanged nitrogen operation was performed to place the reaction flask in a nitrogen atmosphere, 50 mL of a mixed solvent of tetrahydrofuran / deionized water (V / V=3:1) was added, and the mixture was refluxed at 70°C for 24 h; cooled to room temperature, the reaction solution was placed in dichloromethane, extracted with water several times, and then dried with anhydrous MgSO4, filtered, and the solvent in the mixed solution was removed by rotary evaporation. Hexane / dichloromethane was used as an eluent, and the eluent was removed by rotary evaporation to obtain a hole functional material. (hereinafter referred to as T1). The reaction formula for the fifth reactant and the third intermediate product to form the hole functional material is:

[0098]

[0099] In this example, the yield of hole-functional material T1 was 59%. 1H NMR (500 MHz, CDCl3), δ (TMS, ppm): 8.81 (s, 1H), 8.14-8.12 (d 1H), 8.03-8.02 (d, 1H), 7.70-7.68 (d, 1H), 7.23-7.20 (m, 8H), 6.94 (s 1H), 6.83-6.81 (m, 4H), 6.63-6.69 (m 12H), 4.03 (s, 1H), 3.37-3.35 (m, 2H), 1.49-1.31 (m, 4H), 0.92-0.89 (m, 3H).

[0100] Example 2

[0101] In this embodiment, the first reactant is The second reactant is The third reactant is The fourth reactant is liquid bromine Br2, and the fifth reactant is

[0102] (1) 2 mmol of the first reactant, 1 mmol of the second reactant, 0.05 mmol of tetrakistriphenylphosphine palladium and 3 mmol of sodium carbonate were added to a 100 mL two-necked flask in sequence, a magnetic stirring bar was added, and a vacuum-exchanged nitrogen operation was performed to place the reaction flask in a nitrogen atmosphere; 50 mL of a mixed solvent of tetrahydrofuran / deionized water (V / V=3:1) was added, and the mixture was refluxed at 70°C for 24 h; the mixture was cooled to room temperature, and the reaction solution was placed in dichloromethane, extracted with water several times, and then dried with anhydrous MgSO4, filtered, and the solvent in the mixed solution was removed by rotary evaporation. Hexane / dichloromethane was used as an eluent, and the eluent was removed by rotary evaporation to obtain the first intermediate product. The reaction formula for the first reactant and the second reactant to generate the first intermediate product is:

[0103]

[0104] In this embodiment, the first intermediate product The yield was 66%. 1H NMR (500 MHz, CDCl3), 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).

[0105] (2) 1.2 mmol of the third reactant, 1.0 mmol of the first intermediate product and 1.5 mmol of potassium carbonate were added to a 100 mL two-necked flask in sequence, a magnetic stirring bar was added, and a vacuum-exchanged nitrogen operation was performed to place the reaction flask in a nitrogen atmosphere; 50 mL of acetone was added, and the reaction was refluxed at 50° C. for 12 h; the reaction solution was cooled to room temperature, and the reaction solution was placed in dichloromethane, extracted with water several times, and the organic phase was taken, and then dried with anhydrous MgSO4, filtered, and the solvent in the mixed solution was removed by rotary evaporation. Hexane / dichloromethane was used as an eluent, and the eluent was removed by rotary evaporation to obtain the second intermediate product. The reaction formula for the third reactant and the first intermediate product to generate the second intermediate product is:

[0106]

[0107] In this embodiment, the second intermediate product The yield was 89%. 1H NMR (500 MHz, CDCl3), 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).

[0108] (3) 1 mmol of the second intermediate product and 0.05 mmol of ferric bromide were added to a 100 mL two-necked flask in sequence, a magnetic stirring rod was added, and a vacuum-exchanged nitrogen operation was performed to place the reaction flask in 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 reaction solution was extracted with water several times, and the organic phase was taken, then dried with anhydrous MgSO 4 , filtered, and the solvent in the mixed solution was removed by rotary evaporation. Hexane / dichloromethane was used as an eluent, and the eluent was removed by rotary evaporation to obtain the third intermediate product. The reaction formula for the fourth reactant and the second intermediate product to generate the third intermediate product is:

[0109]

[0110] In this embodiment, the third intermediate product The yield was 67%. 1H NMR (500 MHz, CDCl3), 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).

[0111] (4) 1 mmol of the third intermediate product, 3 mmol of the fifth reactant, 0.05 mmol of tetrakistriphenylphosphine palladium and 3 mmol of sodium carbonate were added to a 100 mL two-necked flask in sequence, a magnetic stirring bar was added, and a vacuum-exchanged nitrogen operation was performed to place the reaction flask in a nitrogen atmosphere, 50 mL of a mixed solvent of tetrahydrofuran / deionized water (V / V=3:1) was added, and the mixture was refluxed at 70°C for 24 h; cooled to room temperature, the reaction solution was placed in dichloromethane, extracted with water several times, and then dried with anhydrous MgSO4, filtered, and the solvent in the mixed solution was removed by rotary evaporation. Hexane / dichloromethane was used as an eluent, and the eluent was removed by rotary evaporation to obtain a hole functional material. (hereinafter referred to as T2). The reaction formula for the fifth reactant and the third intermediate product to generate the hole functional material is:

[0112]

[0113] In this example, the yield of hole-functional material T2 was 65%. 1H NMR (500 MHz, CDCl3), δ (TMS, ppm): 8.79 (s, 1H), 8.14-8.12 (d, 1H), 8.03-7.92 (m, 7H), 7.60-7.56 (m, 6H), 7.39-7.36 (d, 2H), 7.01-6.97 (m, 3H), 1.35 (s, 9H).

[0114] Example 3

[0115] In this embodiment, the first reactant is The second reactant is The third reactant is The fourth reactant is liquid bromine Br2, and the fifth reactant is

[0116] (1) 4 mmol of the first reactant, 1 mmol of the second reactant, 0.05 mmol of tetrakistriphenylphosphine palladium and 3 mmol of sodium carbonate were added to a 100 mL two-necked flask in sequence, a magnetic stirring bar was added, and a vacuum-exchanged nitrogen operation was performed to place the reaction flask in a nitrogen atmosphere, 50 mL of a mixed solvent of tetrahydrofuran / deionized water (V / V=3:1) was added, and the mixture was refluxed at 70°C for 24 h; cooled to room temperature, the reaction solution was placed in dichloromethane, extracted with water several times, and then dried with anhydrous MgSO4, filtered, and the solvent in the mixed solution was removed by rotary evaporation. Hexane / dichloromethane was used as an eluent, and the eluent was removed by rotary evaporation to obtain the first intermediate product. The reaction formula for the first reactant and the second reactant to generate the first intermediate product is:

[0117]

[0118] In this embodiment, the first intermediate product The yield 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).

[0119] (2) 2.4 mmol of the third reactant, 1.0 mmol of the first intermediate product and 1.5 mmol of potassium carbonate were added to a 100 mL two-necked flask in sequence, a magnetic stirring bar was added, and a vacuum-exchanged nitrogen operation was performed to place the reaction flask in a nitrogen atmosphere; 50 mL of acetone was added, and the reaction was refluxed at 50° C. for 12 h; the reaction solution was cooled to room temperature, and the reaction solution was placed in dichloromethane, extracted with water several times, and the organic phase was taken, and then dried with anhydrous MgSO4, filtered, and the solvent in the mixed solution was removed by rotary evaporation. Hexane / dichloromethane was used as an eluent, and the eluent was removed by rotary evaporation to obtain the second intermediate product. The reaction formula for the third reactant and the first intermediate product to generate the second intermediate product is:

[0120]

[0121] In this embodiment, the second intermediate product The yield was 76%. 1HNMR (500 MHz, CDCl 3 ), δ (TMS, ppm): 8.83-8.79 (m, 4H), 7.37-7.33 (d, 4H), 7.18-7.15 (m, 2H), 7.01-6.99 (d, 4H), 6.87-6.85 (m, 2H), 6.69-6.66 (m, 2H), 4.03 (s, 2H), 1.35 (s, 18H).

[0122] (3) 1 mmol of the second intermediate product and 0.05 mmol of ferric bromide were added to a 100 mL two-necked flask in sequence, a magnetic stirring rod was added, and a vacuum-exchanged nitrogen gas operation was performed to place the reaction flask in a nitrogen atmosphere; 50 mL of chloroform was added, and 2.1 mmol of the fourth reactant was slowly added dropwise, and the reaction was refluxed at 80° C. for 12 h; the reaction solution was extracted with water several times, the organic phase was taken, and then dried with anhydrous MgSO4, filtered, and the solvent in the mixed solution was removed by rotary evaporation. Hexane / dichloromethane was used as an eluent, and the eluent was removed by rotary evaporation to obtain the third intermediate product. The reaction formula for the fourth reactant and the second intermediate product to generate the third intermediate product is:

[0123]

[0124] In this embodiment, the third intermediate product The yield was 59%. 1HNMR (500 MHz, CDCl 3 ), δ (TMS, ppm): 8.83-8.79 (m, 4H), 7.43-7.37 (m, 6H), 7.04-6.99 (m, 6H), 6.77-6.75 (s, 2H), 4.03 (s, 2H), 1.35 (s, 18H).

[0125] (4) 1 mmol of the third intermediate product, 3 mmol of the fifth reactant, 0.05 mmol of tetrakistriphenylphosphine palladium and 3 mmol of sodium carbonate were added to a 100 mL two-necked flask in sequence, a magnetic stirring bar was added, and a vacuum-exchanged nitrogen operation was performed to place the reaction flask in a nitrogen atmosphere, 50 mL of a mixed solvent of tetrahydrofuran / deionized water (V / V=3:1) was added, and the mixture was refluxed at 70°C for 24 h; cooled to room temperature, the reaction solution was placed in dichloromethane, extracted with water several times, and then dried with anhydrous MgSO4, filtered, and the solvent in the mixed solution was removed by rotary evaporation. Hexane / dichloromethane was used as an eluent, and the eluent was removed by rotary evaporation to obtain a hole functional material. (hereinafter referred to as T3). The reaction formula for the fifth reactant and the third intermediate product to form the hole functional material is:

[0126]

[0127] In this example, the yield of T3 was 59%. 1H NMR (500 MHz, CDCl3), δ (TMS, ppm): 8.79 (s, 2H), 8.03-8.00 (d, 6H), 7.92-7.90 (d, 2H), 7.73-7.71 (d, 2H), 7.62-7.58 (m, 8H), 7.03-6.95 (m, 6H), 6.63-6.61 (d, 2H), 4.03 (s, 2H), 1.35 (s, 18H).

[0128] Example 4

[0129] The difference between this embodiment and embodiment 3 is that the fifth reactant in this embodiment is Wherein, step (4) is:

[0130] (4) Add 2 mmol of the third intermediate product, 6 mmol of the fifth reactant, 2 mmol of potassium carbonate and 0.6 mmol of copper oxide to a 25 mL three-necked flask, add a stirring magnet, and perform a vacuum and nitrogen exchange operation to place the reaction flask in a nitrogen atmosphere. Then add 3 mL of 1-methyl-2-pyrrolidone and reflux at 240° C. for 72 h. After cooling, transfer the reaction solution to a 100 mL three-necked flask, add 40 mL of toluene, reflux for 1 h, and then cool. Filter through diatomaceous earth, extract the filtrate with water several times, and then dry with anhydrous MgSO4, filter, and remove the solvent in the mixed solution by rotary evaporation. Use n-hexane / dichloromethane as eluent, and remove the eluent by rotary evaporation to obtain a hole functional material. (hereinafter referred to as T4). The reaction formula for the fifth reactant and the third intermediate product to form the hole functional material is:

[0131]

[0132] In this example, the yield of hole-functional material T4 was 40%. 1H NMR (500 MHz, CDCl3), δ (TMS, ppm): 8.79 (s, 2H), 8.57-8.55 (d, 2H), 8.12-8.10 (d, 2H), 7.95-7.93 (d, 2H), 7.62-7.59 (d, 2H), 7.54-7.50 (m, 4H), 7.37-7.29 (m, 12H), 7.02-7.00 (d, 4H), 6.70 (s, 2H), 4.03 (s, 2H), 1.35 (s, 18H).

[0133] The present application also provides a mixture comprising an organic compound and at least one organic functional material. The organic compound may be any of the organic compounds described in the preceding embodiments. The structural formula of the organic compound may be as described in the preceding embodiments and will not be repeated here. 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 luminescent material, a host material, or an organic dye.

[0134] The hole injection material may be an organic material such as 3,4-ethylenedioxythiophene: sodium polystyrene sulfonate (PEDOT:PSS), or an inorganic material such as nickel oxide (NiOx), tungsten trioxide (WO3) or molybdenum trioxide (MoO3).

[0135] The hole transport material may be an organic material, such as 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-carbazole)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) One or more; the hole transport material can also be an inorganic material, such as copper oxide (Cu2O) or copper gallium oxide nanoparticles (CuxGa1-xO).

[0136] The electron transport material may include 8-hydroxyquinoline aluminum, 4,7-diphenyl-1,10-phenanthroline, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene, 2-(4'-tert-butylphenyl)-5-(4'-biphenyl)-1,3,4-oxadiazole, 2,9-dimethyl-4,7-biphenyl-1,10-phenanthroline, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H- One or more of 1,2,4-triazole, 4,4'-bis(2,2-distyryl)-1,1'-biphenyl, 2,5-bis(5-tert-butyl-2-benzoxazolyl)thiophene, 8-hydroxyquinoline zinc, 8-hydroxyquinoline gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum, ZnSPB, 2-(4-biphenyl)-5-phenyloxadiazole, 7 2,2'-(1,3-phenyl)bis[5-(4-tert-butylphenyl)-1,3,4-oxadiazole.

[0137] The electron injection material is one or more of poly[(9,9-bis(3'-(N,N-dimethylamino)propyl)fluorenyl-2,7-diyl)-ALT-[(9,9-di-n-octylfluorenyl-2,7-diyl)-bromide (PFN-Br) and poly[(9,9-bis(3'-(N,N-dimethylamino)propyl)-2,7-fluorene)-2,7-(9,9-dioctylfluorene)] (PFN-DOF).

[0138] 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) and 4,4',4"-tris(carbazol-9-yl)triphenylamine (TCTA), and 4,4'-bis(9-carbazol)biphenyl (CBP).

[0139] The hole blocking material may include carbon nanotube-doped polymethyl methacrylate (PMMA) or nano-aluminum oxide-doped PMMA.

[0140] The luminescent material may include one or more of DCM, DCT, DPP, MQA, DCJT, DCJTB, DCJTI, BPVBi, DMQA, TMDBQA, TPBD, PAAA, TAZ, RD3, PtOEP, Ir(BPPa)3, Ir(piq)3, Ir(BPPya)3, Ir(ppy)3, Ir(btpy)3, FCNIr, FIrN4, FIrPic, OXD-(P-NMe2), BPVBi, PPV, MEH-PPV, PPP, Zn(BTZ)2, Be(PP)2, DPAVBi, DPAVB and FIr6.

[0141] 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. The host material may include mCP or TPBi.

[0142] The organic dye may include at least one of a coumarin compound, a quinoxaline derivative, and an anthranilamide derivative.

[0143] The present application provides a composition comprising an organic compound or mixture and at least one organic solvent. The organic compound may be the organic compound described in the preceding embodiment, and the structural formula of the organic compound may refer to the description of the preceding embodiment, which is not repeated here. The mixture may be the mixture described in the preceding embodiment, and the composition of the mixture may refer to the description of the preceding embodiment, which is not repeated here.

[0144] 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 selected according to the type of organic compound, which will not be described in detail here. The present application also 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.

[0145] The first electrode may be a cathode, and 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. This embodiment is described using the hole functional layer as an example, but is not limited thereto.

[0146] In some embodiments, the hole functional layer comprises an organic compound. The organic compound has a structural formula of D-A1-H or D1-A1-D2. The structural formula of the A1 group is The structural formulas of the D group, the D1 group and the D2 group are independently selected from The R group is a hydrogen atom or an alkyl group.

[0147] In this embodiment, the structural formula of the D1 group and the D2 group can be the same, thereby increasing the yield of the organic compound and simplifying the synthesis route. In some embodiments, the structural formula of the D1 group and the D2 group can also be different.

[0148] like Figure 3 As 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, which are arranged in sequence. The substrate layer 10 includes a substrate 101 and a second electrode 102. The second electrode 102 is located on a side of the substrate 101 close to the hole injection layer 11.

[0149] 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 limiting the present application. Furthermore, in some embodiments, the semiconductor device 100 may further include functional layers such as an electron blocking layer and a hole blocking layer, which are not further described here.

[0150] In some embodiments, the hole injection layer 11 may have a thickness of 10 nm to 50 nm. The hole functional layer 12 may have a thickness of 20 nm to 60 nm. The light emitting layer 13 may have a thickness of 20 nm to 60 nm. The electron transport layer 14 may have a thickness of 20 nm to 60 nm. The first electrode 15 may have a thickness of 80 nm to 120 nm.

[0151] It should be noted that the semiconductor device 100 in the present application may be an OLED device or a QLED device. This embodiment is only described by taking the semiconductor device 100 as a QLED device as an example, but is not limited thereto.

[0152] In some embodiments, the hole functional layer 12 includes a mixture, wherein the mixture may be the mixture described in the above embodiment, which will not be described in detail here.

[0153] In some embodiments, the hole functional layer 12 is prepared from a composition, wherein the composition may be the composition described in the above embodiment, which will not be described in detail here.

[0154] The present application provides Examples (1) to (4), and according to methods known in the art, semiconductor device 1 (corresponding to Example (1), hereinafter referred to as "T1 device"), semiconductor device 2 (corresponding to Example (2), hereinafter referred to as "T2 device"), semiconductor device 3 (corresponding to Example (3), hereinafter referred to as "T3 device"), and semiconductor device 4 (corresponding to Example (4), hereinafter referred to as "T4 device") are respectively manufactured. In the above examples, the organic compound is a hole transport material.

[0155] Among them, in the T1 device to the T4 device, the thickness 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 in each film layer are all the same. Specifically, the material of the second electrode 102 is indium tin oxide, with a thickness of 40nm. The material of the hole injection layer 11 is poly (3,4-ethylenedioxythiophene) (PEDOT): sodium polystyrene sulfonate (PSS), with a thickness of 20nm. The material of the light-emitting layer 13 is red light quantum dots, with a thickness of 20nm. The material of the electron transport layer 14 is zinc oxide, with a thickness of 50nm. The material of the first electrode 15 is aluminum, with a thickness of 120nm.

[0156] The thickness of the hole functional layer 12 in the T1 device to the T4 device is the same, which is 30 nm. The difference between the T1 device and the T4 device is that the hole functional layer 12 uses different hole functional materials. The hole functional material used in the hole functional layer 12 of the T2 device is The hole functional material used in the hole functional layer 12 of the T3 device is The hole functional material used in the hole functional layer 12 of the T4 device is

[0157] It should be noted that the hole functional materials used in the T1 device to the T4 device are respectively prepared by the aforementioned hole functional material preparation methods in Examples 1 to 4, which will not be described in detail here.

[0158] The present application also provides a comparative example, which is different from the above-mentioned examples (1) to (4) in 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 recorded as "R1 device".

[0159] Through the experiment, it was determined that the R1 device, T1 device-T4 device had the same brightness (1000cd / m 2 ) under current density, voltage, current efficiency and color coordinates. Figure 1is a graph of current density and voltage for R1 device and T1 device-T4 device, Figure 2 is a graph showing the current efficiency versus current density of the R1 device and the T1-T4 device. Table 1 illustrates the current efficiency of the R1 device and the T1-T4 device at their respective corresponding color coordinates.

[0160] Table 1

[0161]

[0162] Comparative analysis shows that devices T1 through T4, fabricated using the hole-functionalized materials of this application, exhibit high current efficiency. Because the hole-functionalized materials provided herein have a simple synthesis route, using these materials to fabricate semiconductor devices not only achieves high device efficiency but also reduces device manufacturing costs.

[0163] Compared with the organic compounds in the prior art, the present application uses 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 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 of electrons on the nitrogen atom, thereby realizing a preparation process for small molecule materials with a simple synthesis route.

[0164] The above is a detailed introduction to a material and its preparation method, mixture, composition and semiconductor device provided in the embodiments of the present application. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the method of the present application and its core idea; at the same time, for technical personnel in this field, based on the ideas of the present application, there will be changes in the specific implementation methods and application scope. In summary, the content of this specification should not be understood as a limitation on the present application.

Claims

1. An organic compound, characterized in that The structural formula of the organic compound is , the structural formula of the A1 group is One of the following, wherein the structural formula of the D1 group is selected from , , , , and One of the following: the structural formula of the D2 group is selected from -H, , , , , and One of the following; Wherein, the R group is a hydrogen atom or an alkyl group with 1-18 carbon atoms. 2 . The organic compound according to claim 1 , wherein the D1 group and the D2 group have the same structural formula.

3. The organic compound according to claim 1, wherein the structural formula of the organic compound is , , , and One of them.

4. A method for preparing an organic compound, characterized in that: The structural formula of the organic compound is , the structural formula of the A1 group is One of the following, wherein the structural formula of the D1 group is selected from , , , , and One of the following: the structural formula of the D2 group is selected from -H, , , , , and The method for preparing the organic compound comprises the following steps: Provide a first reactant and a second reactant, wherein the first reactant has the structural formula , the structural formula of the second reactant is , the first reactant and the second reactant react to form a first intermediate product, wherein the structural formula of the first intermediate product is , the X group is halogen; A third reactant is provided, wherein the third reactant has the structural formula , the third reactant and the first intermediate product react to form a second intermediate product, wherein the structural formula of the second intermediate product is , the R group is a hydrogen atom or an alkyl group with 1-18 carbon atoms; A fourth reactant is provided, and the fourth reactant reacts with the second intermediate product to generate a third intermediate product, wherein the fourth reactant is liquid bromine, and the structural formula of the third intermediate product is or ; Providing a fifth reactant, the fifth reactant and the third intermediate product react to form an organic compound, wherein the structural formula of the fifth reactant is , the structural formula of the D group is , , , , and One of them.

5. The method for preparing an organic compound according to claim 4, wherein: The structural formula of the organic compound is , , , and One of them.

6. The method for preparing an organic compound according to claim 4, wherein: In the reaction between the first reactant and the second reactant to generate the first intermediate product, 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.

7. The method for preparing an organic compound according to claim 4, wherein: When the third reactant and the first intermediate product react to generate 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.

8. The method for preparing an organic compound according to claim 4, wherein: When the fourth reactant and the second intermediate product react to generate the third intermediate product, the corresponding relationship between the molar amount of the fourth reactant and the molar amount of the second intermediate product is that 30 mmol of the fourth reactant corresponds to 1 mmol-20 mmol of the second intermediate product.

9. The method for preparing an organic compound according to claim 4, wherein: When the fifth reactant and the third intermediate product react to generate the organic compound, the corresponding relationship between the molar amount of the fifth reactant and the molar amount of the third intermediate product is that 20 mmol of the fifth reactant corresponds to 1 mmol-15 mmol of the third intermediate product.

10. A mixture, characterized in that The method comprises an organic compound according to any one of claims 1 to 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 luminescent material or a host material, and the luminescent material comprises an organic dye.

11. A composition, characterized in that The method comprises the organic compound according to any one of claims 1 to 3 or the mixture according to 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, wherein the functional layers include the organic compound according to any one of claims 1 to 3, or the mixture according to claim 10, or are prepared from the composition according to claim 11.

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