TETRASTYRENE-BASED COMPOUND AND APPLICATION THEREOF AND ELECTRONIC DEVICE USING THE SAME

Abstract

The present application discloses a tetrastyrene-based compound, an application thereof, and an electronic device using the same. The tetrastyrene-based compound has a general structural formula as shown in the following Formula 1:

##STR00001##

The tetrastyrene-based compound includes an aromatic amine and a rigid tetrastyrene structure, wherein the aromatic amine can effectively improve the hole injection and transport performance, and the rigid tetrastyrene structure is conducive to the formation of evaporation materials of melting type.

Claims

1. A tetrastyrene-based compound, having a general structural formula as shown in the following Formula 1: ##STR00068## wherein, in Formula 1, X1 is selected from, ##STR00069## O, N-X.sub.11, or S; X2, X3, X4, and X5 are each independently selected from an arylamine with a general structural formula as shown in Formula 2, a hydrogen, an alkyl group having 1 to 22 carbon atoms, an alkoxy group having 1 to 22 carbon atoms, or a heteroalkyl group having 1 to 22 carbon atoms, a mono- or multi-substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, wherein a heteroatom of the heteroalkyl group is O, N, F, S, or Si, a heteroatom of the heteroaryl group is Si, Ge, N, P, O, S, or Se, and at least one of X2, X3, X4, and X5 is an arylamine with the general structural formula as shown in Formula 2: ##STR00070## X6, X7, X8, X9, X10, and X11 are each independently selected from hydrogen, an alkyl group, an alkoxy group having 1 to 22 carbon atoms, or a heteroalkyl group having 1 to 22 carbon atoms, a mono- or multi-substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, wherein a heteroatom of the heteroalkyl group is O, N, F, S, or Si, and a heteroatom of the heteroaryl group is Si, Ge, N, P, O, S, or Se, or at least two of X2, X3, X4, X5, X6, X7, X8, X9, X10, and X11 are connected to each other to form a monocyclic ring or fused ring of an aromatic ring or a heterocyclic ring when the at least two of X2, X3, X4, X5, X6, X7, X8, X9, X10, and X11 are adjacent aryl groups or heteroaryl groups; and when expressed as “substituted or unsubstituted”, optional substituents of each of the aryl group and the heteroaryl group are each independently selected from H, halogen, —OH, —SH, —CN, —NO.sub.2, and an alkylthio group having 1 to 15 carbon atoms, an alkyl group having 1 to 40 carbon atoms, or a substituted alkyl group having 1 to 40 carbon atoms.

2. The tetrastyrene-based compound according to claim 1, wherein a general structural formula of X1 is ##STR00071## and a general structural formula of the tetrastyrene-based compound is shown in the following Formula 3: ##STR00072## wherein, in Formula 3, X3, X4, X6, and X7 are each independently selected from a mono- or multi-substituted, or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or at least two of X3, X4, X6, and X7 are connected to each other to form a monocyclic ring or fused ring of an aromatic ring or a heterocyclic ring when the at least two of X3, X4, X6, and X7 are adjacent aryl groups or heteroaryl groups.

3. The tetrastyrene-based compound according to claim 2, wherein a structure of the tetrastyrene-based compound is represented by any one of the following general Formulas 301-320: ##STR00073## ##STR00074## ##STR00075## ##STR00076## ##STR00077##

4. The tetrastyrene-based compound according to claim 1, wherein a general structural formula of X1 is O, and a general structural formula of the tetrastyrene-based compound is shown in the following Formula 4: ##STR00078## wherein, in Formula 4, X3, X4, X6, and X7 are each independently selected from a mono- or multi-substituted, or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or at least two of X3, X4, X6, and X7 are connected to each other to form a monocyclic ring or fused ring of an aromatic ring or a heterocyclic ring when the at least two of X3, X4, X6, and X7 are adjacent aryl groups or heteroaryl groups.

5. The tetrastyrene-based compound according to claim 4, wherein a structure of the tetrastyrene-based compound is represented by any one of the following general Formulas 401-420: ##STR00079## ##STR00080## ##STR00081## ##STR00082## ##STR00083##

6. The tetrastyrene-based compound according to claim 1, wherein a general structural formula of X1 is N-ph, and a general structural formula of the tetrastyrene-based compound is shown in Formula 5 below: ##STR00084## wherein, in Formula 5, X3, X4, X6, and X7 are each independently selected from a mono- or multi-substituted, or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or at least two of X3, X4, X6, and X7 are connected to each other to form a monocyclic ring or fused ring of an aromatic ring or a heterocyclic ring when the at least two of X3, X4, X6, and X7 are adjacent aryl groups or heteroaryl groups.

7. The tetrastyrene-based compound according to claim 6, wherein a structure of the tetrastyrene-based compound is represented by any one of the following general Formulas 501-520: ##STR00085## ##STR00086## ##STR00087## ##STR00088## ##STR00089##

8. An application of the tetrastyrene-based compound according to claim 1 as an electroluminescent organic material in an electronic device.

9. An electronic device, comprising a substrate, an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers containing the tetrastyrene-based compound according to claim 1.

10. The electronic device according to claim 9, wherein the organic material layer comprises a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a light-emitting layer.

Description

DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS

[0024] Details of the tetrastyrene-based compound and electronic device using the same provided in the embodiments of the present application is explained and described as follows.

[0025] The general structural formula of the tetrastyrene-based compound provided in an embodiment of the present application is shown in the following formula 1:

##STR00028##

[0026] In Formula 1, X1 is selected from,

##STR00029##

O, N-X.SUB.11 .or S;

[0027] X2, X3, X4, and X5 are each independently selected from an arylamine with a general structural formula as shown in Formula 2, a hydrogen, an alkyl group having 1 to 22 carbon atoms, an alkoxy group having 1 to 22 carbon atoms, or a heteroalkyl group having 1 to 22 carbon atoms, a mono- or multi-substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, wherein a heteroatom of the heteroalkyl group is O, N, F, S, or Si, a heteroatom of the heteroaryl group is Si, Ge, N, P, O, S, or Se, and at least one of X2, X3, X4, and X5 is an arylamine with the general structural formula as shown in Formula 2:

##STR00030##

[0028] In the above formula, X6, X7, X8, X9, X10, and X11 are each independently selected from hydrogen, an alkyl group, an alkoxy group having 1 to 22 carbon atoms, or a heteroalkyl group having 1 to 22 carbon atoms, a mono- or multi-substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, wherein a heteroatom of the heteroalkyl group is O, N, F, S, or Si, and a heteroatom of the heteroaryl group is Si, Ge, N, P, O, S, or Se, or at least two of X2, X3, X4, X5, X6, X7, X8, X9, X10, and X11 are connected to each other to form a monocyclic ring or fused ring of an aromatic ring or a heterocyclic ring when the at least two of X2, X3, X4, X5, X6, X7, X8, X9, X10, and X11 are adjacent aryl groups or heteroaryl groups; and [0029] when expressed as “substituted or unsubstituted”, optional substituents of each of the aryl group and the heteroaryl group are each independently selected from H, halogen, —OH, —SH, —CN, —NO.sub.2, and an alkylthio group having 1 to 15 carbon atoms, an alkyl group having 1 to 40 carbon atoms, or a substituted alkyl group having 1 to 40 carbon atoms.

[0030] It can be seen that the tetrastyrene-based compound of the above embodiment contains a rigid tetrastyrene structure and an aromatic amine, wherein the aromatic amine can effectively improve the hole injection and transport performance, thereby improving the balance of electrons and holes of the organic light-emitting diode; and the rigid tetrastyrene structure is conducive to the formation of evaporation materials of melting type, thereby being conducive to the stability of mass production evaporation.

[0031] In a preferred embodiment of the present application, a general structural formula of X1 can be

##STR00031##

and a general structural formula of the tetrastyrene-type compound can be as shown in the following Formula 3:

##STR00032##

[0032] In Formula, X3, X4, X6, and X7 are each independently selected from a mono- or multi-substituted, or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or at least two of X3, X4, X6, and X7 are connected to each other to form a monocyclic ring or fused ring of an aromatic ring or a heterocyclic ring when the at least two of X3, X4, X6, and X7 are adjacent aryl groups or heteroaryl groups.

[0033] Furthermore, a structure of the tetrastyrene-based compound is represented by any one of the following general Formulas 301-320:

##STR00033## ##STR00034## ##STR00035## ##STR00036## ##STR00037## ##STR00038## ##STR00039##

[0034] In another preferred embodiment of the present application, a general structural formula of X1 is O, and a general structural formula of the tetrastyrene-based compound is shown in the following Formula 4:

##STR00040##

[0035] In Formula 4, X3, X4, X6, and X7 are each independently selected from a mono- or multi-substituted, or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or at least two of X3, X4, X6, and X7 are connected to each other to form a monocyclic ring or fused ring of an aromatic ring or a heterocyclic ring when the at least two of X3, X4, X6, and X7 are adjacent aryl groups or heteroaryl groups.

[0036] Furthermore, a structure of the tetrastyrene-based compound is represented by any one of the following general Formulas 401-420:

##STR00041## ##STR00042## ##STR00043## ##STR00044## ##STR00045##

[0037] In further another preferred embodiment of the present application, a general structural formula of X1 is N-ph, and a general structural formula of the tetrastyrene-based compound is shown in Formula 5 below:

##STR00046##

[0038] In Formula 5, X3, X4, X6, and X7 are each independently selected from a mono- or multi-substituted, or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or at least two of X3, X4, X6, and X7 are connected to each other to form a monocyclic ring or fused ring of an aromatic ring or a heterocyclic ring when the at least two of X3, X4, X6, and X7 are adjacent aryl groups or heteroaryl groups.

[0039] Furthermore, a structure of the tetrastyrene-based compound is represented by any one of the following general Formulas 501-520:

##STR00047## ##STR00048## ##STR00049## ##STR00050## ##STR00051## ##STR00052## ##STR00053##

[0040] Another embodiment of the present application provides an application of the above-mentioned tetrastyrene-based compound as an electroluminescent organic material in an electronic device.

[0041] Still another embodiment of the present application provides an electronic device including a substrate, an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers containing the tetrastyrene-based compound of the above-mentioned embodiments, wherein the organic material layer may include a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a light-emitting layer. Here, the electronic device may be an electroluminescent device, such as an organic light-emitting diode device.

[0042] Hereinafter, methods of preparing the tetrastyrene-based compound provided in the above embodiments of the present application will be described.

EXAMPLE 1

[0043] The synthesis reaction of the tetrastyrene-based compound of target structure 1 is shown in Scheme 6:

##STR00054##

[0044] The method of preparing the tetrastyrene-based compound of the target structure 1 provided in Example 1 is as follows:

[0045] Compound (1) (6 mmol, 1.02 g), Compound (2) (5 mmol, 1.37 g), CuI (0.3 mmol, 0.06 g), potassium carbonate (K.sub.2CO.sub.3, 5 mmol, 0.69 g), and 50mL of 1,4-dioxane were added into a 100 mL two-necked bottle, and stirred and heated to 100° C. under argon atmosphere for a reaction for 12 hour, which was then dissolved with dichloromethane (300 mL) and added with saturated NH.sub.4Cl (200 mL) solution, extracted by dichloromethane, dried by the organic phase with anhydrous sodium sulfate, and concentrated, followed by column separation, wherein 200-300 mesh silica gel was used as a stationary phase, and dichloromethane was used as an eluent, to obtain an intermediate, 1.64 g of Compound (3), with a yield of 91%.

[0046] The product, Compound (3) (4.6 mmol, 1.64 g), from the previous steps, Compound (4) (5.0 mmol, 2.26 g), t-BuONa (8 mmol, 0.76 g), Pd.sub.2(dba).sub.3 (0.09 mmol, 81 mg), P(t-Bu).sub.3/HBF.sub.4 (0.92 mmol, 0.24 g), and 50 mL anhydrous and deoxygenated toluene were added into a 100 mL two-necked flask, reacted at 98° C. overnight, and cooled to room temperature. Then, the reaction solution was concentrated, followed by separated and purified by column chromatography to obtain 2.15 g of white powdery target structure 1, with a yield of 64%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): calculated value m/z, 731.98; measured value m/z, 731.12. Elemental analysis (EA): calculated value: carbon C, 91.89; hydrogen H, 6.20; nitrogen N, 1.91; measured value: carbon C, 91.79; hydrogen H, 6.43; nitrogen N, 1.78.

EXAMPLE 2

[0047] The synthesis reaction of the tetrastyrene-based compound of target structure 2 is shown in Scheme 7:

##STR00055##

[0048] The method of preparing the tetrastyrene-based compound of the target structure 2 provided in Example 2 is as follows:

[0049] Compound (5) (6 mmol, 1.02 g), Compound (6) (5 mmol, 1.45 g), CuI (0.3 mmol, 0.06 g), potassium carbonate (K.sub.2CO.sub.3, 5 mmol, 0.69 g), and 50 mL of 1,4-dioxane were added into a 100 mL two-necked bottle, and stirred and heated to 100° C. under argon atmosphere for a reaction for 12 hour, which was then dissolved with dichloromethane (300 mL) and added with saturated NH.sub.4Cl (200 mL) solution, extracted by dichloromethane, dried by the organic phase with anhydrous sodium sulfate, and concentrated, followed by column separation, wherein 200-300 mesh silica gel was used as a stationary phase, and dichloromethane was used as an eluent, to obtain an intermediate, 1.67 g of Compound (7), with a yield of 85%.

[0050] The product, Compound (7) (4.3 mmol, 1.67 g), from the previous steps, Compound (4) (5.0 mmol, 2.26 g), t-BuONa (8 mmol, 0.76 g), Pd.sub.2(dba).sub.3 (0.09 mmol, 81 mg), P(t-Bu).sub.3/HBF.sub.4 (0.92 mmol, 0.24 g), and 50 mL anhydrous and deoxygenated toluene were added into a 100 mL two-necked flask, reacted at 98° C. overnight, and cooled to room temperature. Then, the reaction solution was concentrated, followed by separated and purified by column chromatography to obtain 2.41 g of white powdery target structure 2, with a yield of 75%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): calculated value m/z, 748.03; measured value m/z, 748.57. Elemental analysis (EA): calculated value: carbon C, 91.52; hydrogen H, 6.60; nitrogen N, 1.87; measured value: carbon C, 91.74; hydrogen H, 6.53; nitrogen N, 1.73.

EXAMPLE 3

[0051] The synthesis reaction of the tetrastyrene-based compound of the target structure 3 is shown in the Scheme 8:

##STR00056##

[0052] The method of preparing the tetrastyrene-based compound of the target structure 3 provided in Example 3 is as follows:

[0053] Compound (8) (5 mmol, 1.60 g), Compound (4) (5.0 mmol, 2.48 g), t-BuONa (8 mmol, 0.76 g), Pd.sub.2(dba).sub.3 (0.09 mmol, 81 mg), P(t-Bu).sub.3/HBF.sub.4 (0.92 mmol, 0.24 g), and 50 mL anhydrous and deoxygenated toluene were added into a 100 mL two-necked flask, reacted at 98° C. overnight, and cooled to room temperature. Then, the reaction solution was concentrated, followed by separated and purified by column chromatography to obtain 2.70 g of white powdery target structure 3, with a yield of 80%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): calculated value m/z, 674.87; measured value m/z, 674.35. Elemental analysis (EA): calculated value: carbon C, 92.55; hydrogen H, 5.38; nitrogen N, 2.08; measured value: carbon C, 92.10; hydrogen H, 5.56; nitrogen N, 2.34.

EXAMPLE 4

[0054] The synthesis reaction of the tetrastyrene-based compound of target structure 4 is shown in Scheme 9:

##STR00057##

[0055] The method of preparing the tetrastyrene-based compound of the target structure 4 provided in Example 4 is as follows:

[0056] Compound (9) (5mmol, 1.70 g), Compound (4) (5.0 mmol, 2.48 g), t-BuONa (8 mmol, 0.76 g), Pd.sub.2(dba).sub.3 (0.09 mmol, 81 mg), P(t-Bu).sub.3/HBF.sub.4 (0.92 mmol, 0.24 g), and 50 mL anhydrous and deoxygenated toluene were added into a 100 mL two-necked flask, reacted at 98° C. overnight, and cooled to room temperature. Then, the reaction solution was concentrated, followed by separated and purified by column chromatography to obtain 2.55 g of white powdery target structure 4, with a yield of 72%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): calculated value m/z, 709.38; measured value m/z, 709.11. Elemental analysis (EA): calculated value: carbon C, 91.35; hydrogen H, 6.67; nitrogen N, 1.97; measured value: C, 91.57; H, 6.03; N, 2.40.

EXAMPLE 5

[0057] The synthesis reaction of the tetrastyrene-based compound of target structure 5 is shown in Scheme 10:

##STR00058##

[0058] The method of preparing the tetrastyrene-based compound of the target structure 5 provided in Example 5 is as follows:

[0059] Compound (9) (5mmol, 1.70 g), Compound (10) (5.5 mmol, 2.48 g), t-BuONa (8 mmol, 0.76 g), Pd.sub.2(dba).sub.3 (0.09 mmol, 81 mg), P(t-Bu).sub.3/HBF.sub.4 (0.92 mmol, 0.24 g), and 50 mL anhydrous and deoxygenated toluene were added into a 100 mL two-necked flask, reacted at 98° C. overnight, and cooled to room temperature. Then, the reaction solution was concentrated, followed by separated and purified by column chromatography to obtain 2.31 g of white powdery target structure 5 with a yield of 65%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): calculated value m/z, 709.38; measured value m/z, 709.15. Elemental analysis method (EA): calculated value: carbon C, 91.35; hydrogen H, 6.67; nitrogen N, 1.97; measured value: C, 91.41; H, 6.53; N, 2.06.

EXAMPLE 6

[0060] The synthesis reaction of the tetrastyrene-based compound of target structure 6 is shown in Scheme 11:

##STR00059##

[0061] The method of preparing the tetrastyrene-based compound of the target structure 6 provided in Example 6 is as follows:

[0062] Compound (3) (4.0 mmol, 1.45 g), Compound (11) (5.0 mmol, 2.13 g), t-BuONa (8 mmol, 0.76 g), Pd.sub.2(dba).sub.3 (0.09 mmol, 81 mg), P(t-Bu).sub.3/HBF.sub.4 (0.92 mmol, 0.24 g), and 50 mL anhydrous and deoxygenated toluene were added into a 100 mL two-necked flask, reacted at 98° C. overnight, and cooled to room temperature. Then, the reaction solution was concentrated, followed by separated and purified by column chromatography to obtain 2.20 g of white powdery target structure 6, with a yield of 78%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): calculated value m/z, 705.94; measured value m/z, 705.19. Elemental analysis (EA): calculated value: carbon C, 91.18; hydrogen H, 5.57; nitrogen N, 1.98; measured value: C, 91.32; H, 5.71; N, 1.84.

EXAMPLE 7

[0063] The synthesis reaction of the tetrastyrene-based compound of target structure 7 is shown in Scheme 12:

##STR00060##

[0064] The method of preparing the tetrastyrene-based compound of the target structure 7 provided in Example 7 is as follows:

[0065] Compound (7) (4.0 mmol, 1.57 g), Compound (11) (5.0 mmol, 2.13 g), t-BuONa (8 mmol, 0.76 g), Pd.sub.2(dba).sub.3 (0.09 mmol, 81 mg), P(t-Bu).sub.3/HBF.sub.4 (0.92 mmol, 0.24 g), and 50 mL anhydrous and deoxygenated toluene were added into a 100 mL two-necked flask, reacted at 98° C. overnight, and cooled to room temperature. Then, the reaction solution was concentrated, followed by separated and purified by column chromatography to obtain 1.99 g of white powdery target structure 7 with a yield of 69%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): calculated value m/z, 721.94; measured value m/z, 721.87. Elemental analysis (EA): calculated value: carbon C, 89.84; hydrogen H, 6.00; nitrogen N, 1.94; measured value: C, 90.05; H, 5.92; N, 1.99.

EXAMPLE 8

[0066] The synthesis reaction of the tetrastyrene-based compound of target structure 8 is shown in Scheme 13:

##STR00061##

[0067] The method of preparing the tetrastyrene-based compound of the target structure 8 provided in Example 8 is as follows:

[0068] Compound (8) (4.0 mmol, 1.28 g), Compound (11) (5.0 mmol, 2.13 g), t-BuONa (8 mmol, 0.76 g), Pd.sub.2(dba).sub.3 (0.09 mmol, 81 mg), P(t-Bu).sub.3/HBF.sub.4 (0.92 mmol, 0.24 g), and 50 mL anhydrous and deoxygenated toluene were added into a 100 mL two-necked flask, reacted at 98° C. overnight, and cooled to room temperature. Then, the reaction solution was concentrated, followed by separated and purified by column chromatography to obtain 1.86 g of white powdery target structure 8, with a yield of 70%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): calculated value m/z, 663.82; measured value m/z, 663.19. Elemental analysis method (EA): calculated value: carbon C, 90.47; hydrogen H, 5.01; nitrogen N, 2.11; measured value: C, 90.13; H, 5.32; N, 2.01.

EXAMPLE 9

[0069] The synthesis reaction of the tetrastyrene-based compound of target structure 9 is shown in Scheme 14:

##STR00062##

[0070] The method of preparing the tetrastyrene-based compound of the target structure 9 provided in Example 9 is as follows:

[0071] Compound (12) (4.0 mmol, 1.30 g), Compound (11) (5.0 mmol, 2.13 g), t-BuONa (8 mmol, 0.76 g), Pd.sub.2(dba).sub.3 (0.09 mmol, 81 mg), P(t-Bu).sub.3/HBF.sub.4 (0.92 mmol, 0.24 g), and 50 mL anhydrous and deoxygenated toluene were added into a 100 mL two-necked flask, reacted at 98° C. overnight, and cooled to room temperature. Then, the reaction solution was concentrated, followed by separated and purified by column chromatography to obtain 2.00 g of white powdery target structure 9, with a yield of 73%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): calculated value m/z, 683.9; measured value m/z, 683.53. Elemental analysis method (EA): calculated value: carbon C, 89.57; hydrogen H, 6.04; nitrogen N, 2.05; measured value: C, 89.37; H, 6.21; N, 1.86.

EXAMPLE 10

[0072] The synthesis reaction of the tetrastyrene-based compound of target structure 10 is shown in Scheme 15:

##STR00063##

[0073] The method of preparing the tetrastyrene-based compound of the target structure 10 provided in Example 10 is as follows:

[0074] Compound (12) (4.0 mmol, 1.30 g), Compound (13) (5.0 mmol, 2.13 g), t-BuONa (8 mmol, 0.76 g), Pd.sub.2(dba).sub.3 (0.09 mmol, 81 mg), P(t-Bu).sub.3/HBF.sub.4 (0.92 mmol, 0.24 g), and 50 mL anhydrous and deoxygenated toluene were added into a 100 mL two-necked flask, reacted at 98° C. overnight, and cooled to room temperature. Then, the reaction solution was concentrated, followed by separated and purified by column chromatography to obtain 1.67 g of white powdery target structure 10 with a yield of 61%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): calculated value m/z, 683.9; measured value m/z, 683.64. Elemental analysis method (EA): calculated value: carbon C, 89.57; hydrogen H, 6.04; nitrogen N, 2.05; measured value: C, 89.45; H, 6.09; N, 2.14.

EXAMPLE 11

[0075] The synthesis reaction of the tetrastyrene-based compound of target structure 11 is shown in Scheme 16:

##STR00064##

[0076] The method of preparing the tetrastyrene-based compound of the target structure 11 provided in Example 11 is as follows:

[0077] Compound (3) (4.6 mmol, 1.64 g), Compound (14) (5.0 mmol, 2.50 g), t-BuONa (8 mmol, 0.76 g), Pd.sub.2(dba).sub.3 (0.09 mmol, 81 mg), P(t-Bu).sub.3/HBF.sub.4 (0.92 mmol, 0.24 g), and 50 mL anhydrous and deoxygenated toluene were added into a 100 mL two-necked flask, reacted at 98° C. overnight, and cooled to room temperature. Then, the reaction solution was concentrated, followed by separated and purified by column chromatography to obtain 2.28 g of white powdery target structure 11 with a yield of 73%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): calculated value m/z, 781.02; measured value m/z, 780.93. Elemental analysis (EA): calculated value carbon: C, 90.73; hydrogen H, 5.68; nitrogen N, 3.59; measured value: C, 90.85; H, 5.72; N, 3.43.

EXAMPLE 12

[0078] The synthesis reaction of the tetrastyrene-based compound of the target structure 12 is shown in the Scheme 17:

##STR00065##

[0079] The method of preparing the tetrastyrene-based compound of the target structure 12 provided in Example 12 is as follows:

[0080] Compound (7) (4.0mmol, 1.57 g), Compound (14) (5.0 mmol, 2.50 g), t-BuONa (8 mmol, 0.76 g), Pd.sub.2(dba).sub.3 (0.09 mmol, 81 mg), P(t-Bu).sub.3/HBF.sub.4 (0.92 mmol, 0.24 g), and 50 mL anhydrous and deoxygenated toluene were added into a 100 mL two-necked flask, reacted at 98° C. overnight, and cooled to room temperature. Then, the reaction solution was concentrated, followed by separated and purified by column chromatography to obtain 2.07 g of white powdery target structure 12 with a yield of 65%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): calculated value m/z, 797.06; measured value m/z, 797.53. Elemental analysis method (EA): calculated value: carbon C, 90.42; hydrogen H, 6.07; nitrogen N, 3.51; measured value: C, 90.35; H, 5.98; N, 3.67.

EXAMPLE 13

[0081] The synthesis reaction of the tetrastyrene-based compound of target structure 13 is shown in Scheme 18:

##STR00066##

[0082] The method of preparing the tetrastyrene-based compound of the target structure 13 provided in Example 13 is as follows:

[0083] Compound (8) (4.0 mmol, 1.28 g), Compound (14) (5.0 mmol, 2.50 g), t-BuONa (8 mmol, 0.76 g), Pd.sub.2(dba).sub.3 (0.09 mmol, 81 mg), P(t-Bu).sub.3/HBF.sub.4 (0.92 mmol, 0.24 g), and 50 mL anhydrous and deoxygenated toluene were added into a 100 mL two-necked flask, reacted at 98° C. overnight, and cooled to room temperature. Then, the reaction solution was concentrated, followed by separated and purified by column chromatography to obtain 2.13 g of white powdery target structure 13, with a yield of 72%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): calculated value m/z, 738.93; measured value m/z, 738.69. Elemental analysis (EA): calculated value: carbon C, 91.03; hydrogen H, 5.18; nitrogen N, 3.79; measured value: C, 91.48; H, 5.21; N, 3.31.

EXAMPLE 14

[0084] The synthesis reaction of the tetrastyrene-based compound of the target structure 14 is shown in the Scheme 19:

##STR00067##

[0085] The method of preparing the tetrastyrene-based compound of the target structure 14 provided in Example 14 is as follows:

[0086] Compound (12) (4.0 mmol, 1.30 g), Compound (14) (5.0 mmol, 2.50 g), t-BuONa (8 mmol, 0.76 g), Pd.sub.2(dba).sub.3 (0.09 mmol, 81 mg), P(t-Bu).sub.3/HBF.sub.4 (0.92 mmol, 0.24 g), and 50 mL anhydrous and deoxygenated toluene were added into a 100 mL two-necked flask, reacted at 98° C. overnight, and cooled to room temperature. Then, the reaction solution was concentrated, followed by separated and purified by column chromatography to obtain 1.88 g of white powdery target structure 14, with a yield of 62%. Matrix-assisted laser desorption ionization time-of-flight mass spectrometer (MALDI-TOF): calculated value m/z, 759.01; measured value m/z, 759.25. Elemental analysis method (EA): calculated value: carbon C, 90.20; hydrogen H, 6.11; nitrogen N, 3.69; measured value: C, 90.37; H, 6.35; N, 3.28.

Test and Experimental Verification

[0087] After test and experimental verification, energy levels of the above-mentioned tetrastyrene-based compounds with target structures 1-14 are shown in Table 1 below:

TABLE-US-00001 TABLE 1 tetrastyrene-based Eg HOMO T1 compound (eV) (eV) (eV) target structure 1 3.13 −5.35 2.67 target structure 2 3.23 −5.34 2.71 target structure 3 3.03 −5.58 2.59 target structure 4 3.29 −5.62 2.73 target structure 5 3.39 −5.56 2.81 target structure 6 3.1 −5.37 2.65 target structure 7 3.23 −5.41 2.69 target structure 8 3.38 −5.63 2.74 target structure 9 3.1 −5.67 2.59 target structure 10 3.42 −5.65 2.87 target structure 11 3.35 −5.21 2.78 target structure 12 3.37 −5.25 2.81 target structure 13 3.32 −5.35 2.79 target structure 14 3.35 −5.37 2.78

[0088] An electronic device provided in an embodiment of the present application is manufactured according to a method known in the art. Taking an electroluminescent device as the electronic device as an example, the device structure may specifically include an ITO layer, a HAT-CN layer (for example, having a thickness of 5 nm), and an organic material layer of a tetrastyrene-based compound with any of the above target structures (for example, having a thickness of 30 nm), a Firpic:B3PyPB layer (12%, 10 nm), a TPBi layer (for example, having a thickness of 40 nm), a LiF layer (for example, having a thickness of 2 nm), and an aluminum Al layer (for example, having a thickness of 100nm). After test and experimental verification, for each of the above-mentioned tetrastyrene-based compounds of the target structures 1-14, the performance data of the electroluminescent devices whose organic material layers contain the tetrastyrene-based compounds of the target structures, respectively, is shown in Table 2 below:

TABLE-US-00002 TABLE 2 Highest Maximum external organic material Voltage efficiency quantum efficiency layer (v) (cd/A) (%) target structure 1 3.4 26.3 12.1 target structure 2 3.5 23.6 12.2 target structure 3 3.8 21.5 11.3 target structure 4 3.8 25.7 11.9 target structure 5 3.9 19.5 11.2 target structure 6 3.4 27.9 12.9 target structure 7 3.5 33.2 13.5 target structure 8 3.7 28.1 12.9 target structure 9 3.9 19.7 9.6 target structure 10 4.1 13.5 8.7 target structure 11 3.2 31.5 12.8 target structure 12 3.3 35.7 13.5 target structure 13 3.1 31.4 13.2 target structure 14 3.4 36.2 14.2

[0089] Embodiments of the present application provide a tetrastyrene-based compound, an application thereof, and an electronic device using the same, wherein the tetrastyrene-based compound includes an aromatic amine and a rigid tetrastyrene structure, the aromatic amine can effectively improve the hole injection and transport performance, thereby improving the balance of electrons and holes of the organic light-emitting diode, achieving a lower voltage and higher efficiency; and the rigid tetrastyrene structure is conducive to the formation of evaporation materials of melting type, thereby being conducive to the stability of mass production evaporation. Such materials can achieve high-efficiency preparation of electroluminescent devices, and can be used in the manufacture of display devices

[0090] While the invention has been described by way of example and in terms of the preferred embodiments, it is to be understood that the invention is not limited to the disclosed embodiments. To the contrary, it is intended to cover various modifications and similar arrangements. Therefore, the scope of the appended claims should be accorded the broadest interpretation so as to encompass all such modifications and similar arrangements.