Fused ring compound and application thereof in organic electroluminescent device

Abstract

To provide a fused ring compound capable of remarkably improving the performance of an organic electroluminescent device and achieving high efficiency, long service life, and excellent color purity, and an organic electroluminescent device having a luminescent layer including the fused ring compound.SOLUTION: The present invention provides a fused ring compound having a chemical structural formula represented by formula (I), formula (II), or formula (III). Specifically, it is a compound synthesized by using naphthofurofluorene, naphthofurofuran, naphthofluorene-furan, naphthofluorene-fluorene, naphthothieno-furan, naphthothieno-fluorene, or naphthothieno-thiophene as a core parent nucleus and introducing fused ring molecules at specific positions.SELECTED DRAWING: Figure 1

Description

Technical Field

[0001] The present invention belongs to the technical field of organic electroluminescent materials, and relates to a condensed ring compound and its application to an organic electroluminescent device.

Background Art

[0002] As a new solid-state light-emitting technology, organic electroluminescent devices have developed rapidly and are gradually being industrialized. An organic electroluminescent device usually includes an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and a cathode structure. Under the action of an external electric field, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet in the light-emitting layer, excitons are formed. When the excitons jump back to the ground state, they release energy and emit light. In order to improve the optoelectronic properties such as the efficiency, luminance, and lifespan of the device, it is usually necessary to dope a light-emitting material into a suitable host material to reduce the exciton quenching effect, thereby improving the light-emitting performance of the device. Therefore, to obtain high-quality device performance, a high-performance host material is indispensable, and how to develop a high-quality host material has always been a difficult and hot issue in the industry.

[0003] Condensed ring compounds have high thermal stability due to the unique molecular conjugate structure in the molecule. The host material prepared by appropriate group modification can obtain better frontier orbital energy levels, and can improve the performance of the device such as efficiency, lifespan, and color purity as a host material, and industrial application is expected.

Summary of the Invention

Problems to be Solved by the Invention

[0004] The present invention aims to provide a condensed ring compound and its application to an organic electroluminescence device. By fully utilizing the rigidity and torsional properties of naphthofluorenofuran, naphthofuranofluorene, naphthofuranofuran, naphthofuranothiophene, naphthofluorenofluorene, naphthofluorenothiophene, naphthothienothiophene, naphthothienofuran, and naphthothienofluorene, the triplet energy of the material is improved. Specific substitution positions are further modified or deuterated with condensed ring groups such as anthracene, naphthalene, pyrene, xanthene, spirofluorene, and phenanthrofuran. This type of compound can be applied to an organic electroluminescence device as a host material for the light-emitting layer, significantly improving the performance of the organic electroluminescence device and achieving high efficiency, long lifespan, and excellent color purity.

Means for Solving the Problems

[0005] Based on the above object, on the one hand, the present invention relates to a condensed ring compound having a chemical structural formula as shown in Formula (I), Formula (II), or Formula (III).

[0006]

Chemical Formula

[0007] X is an O atom, an S atom, CR 13 R 14 and Y is an O atom, an S atom, CR 15 R 16 where R 13 , R 14 , R 15 , R 16 are each independently selected from a methyl group or a phenyl group, L is a single bond, a deuterated or non-deuterated phenyl group, a deuterated or non-deuterated naphthyl group, a deuterated or non-deuterated anthryl group, a deuterated or non-deuterated pyrenyl group, a deuterated or non-deuterated chrysenyl group, a deuterated or non-deuterated phenanthryl group, a deuterated or non-deuterated benzoxanthenyl group, a deuterated or non-deuterated phenanthrofuryl group. Ar is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, an aryl group in which a hydrogen atom is partially deuterated, an aryl group in which a hydrogen atom is completely deuterated, a heteroaryl group in which a hydrogen atom is partially deuterated, or a heteroaryl group in which a hydrogen atom is completely deuterated. (Ar) n are n groups selected from Ar, where n is an integer from 0 to 5. R1 to R 12 are each independently selected from hydrogen or deuterium.

[0008] Furthermore, in the condensed ring compound provided by the present invention, the aryl group is any one of a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, a phenanthryl group, a spirofluorenyl group, a phenanthrofuryl group, and a benzoxanthenyl group.

[0009] Furthermore, in the condensed ring compound provided by the present invention, the heteroaryl group is a heteroaryl group containing N, O, or S.

[0010] Furthermore, the condensed ring compound provided by the present invention is characterized in that the compound is one selected from the following structural formulas, where B represents a substituted or unsubstituted phenyl group.

[0011]

Chemical formula

[0012] Furthermore, the condensed ring compound provided by the present invention contains chemical structural formulas shown in Compounds 1 to 190 in the compound.

[0013]

Chemical formula

Chemical formula

Chemical formula

[0014] D indicates that the hydrogen atom has been replaced by deuterium.

[0015] Furthermore, the method for preparing the compound is to mix an intermediate, compound (I), potassium carbonate, tetrabutylammonium bromide, toluene, ethanol and pure water and react them to obtain the compound. The intermediate is any one of intermediate 1, intermediate 2, intermediate 3, intermediate 4, intermediate 5, intermediate 6, intermediate 7, and intermediate 8, and the specific chemical structural formula is as follows.

[0016] [Chemistry]

[0017] Furthermore, the compound (I) is naphthofuranofluorene, naphthofuranofuran, naphthofluorenofuran, naphthofluorenofluorene, naphthothienofuran, naphthothienofluorene, or naphthothienothiophene.

[0018] According to verification, the condensed ring compound provided by the present invention can significantly improve the performance of the light-emitting device, achieving high efficiency, long life, and excellent color purity, and is suitable for use as a light-emitting material in OLED light-emitting devices and display devices. Therefore, the present invention further claims the application of the above-mentioned condensed ring compound in an organic electroluminescence device, manufactures a light-emitting layer as a light-emitting host material, and claims the application to an organic electroluminescence device, thereby further protecting the application of the organic electroluminescence device in an organic electroluminescence display device.

Advantages of the Invention

[0019] Compared with the prior art, the present invention has the following beneficial effects or advantages. The present invention constructs a condensed ring structure with molecular twist by closing the rings of benzofuran, fluorene, and thiophene at specific positions of naphthofuran, naphthofluorene, and naphthothiophene groups. Furthermore, through the modification of the condensed ring molecules, new deuterated or non-deuterated compounds are synthesized. As a blue light host material, the compound has significantly improved luminous efficiency and service life compared with the existing host material BH1. The luminous efficiency of the device has increased by 47.2%, and the device life has increased by 66.7%. And according to verification, the compound of the present invention is applied to an OLED light-emitting device as a host material for the light-emitting layer, and the luminous efficiency and life performance of the device have good performance compared with existing materials. It has great application value in the application of OLED devices and has good prospects for industrialization.

Brief Description of the Drawings

[0020] [Figure 1] It is a schematic diagram of the structure of an organic electroluminescence device manufactured by the present invention.

Embodiments for Carrying Out the Invention

[0021] Hereinafter, the technical solution of the present invention will be described with reference to examples, but the present invention is not limited to the following examples.

[0022] In order for those skilled in the art to better understand and implement the technical solution of the present invention, the present invention will be further described below with reference to specific examples and drawings, but the examples given are not intended to limit the present invention.

[0023] The experimental methods and detection methods described in the following examples are all conventional methods unless otherwise specified, and the reagents and materials described can be purchased on the market unless otherwise specified.

[0024] Example 1 This example provides the synthesis of Intermediate 1. The synthesis route is as follows.

[0025]

Chemical formula

[0026] Synthesis of Intermediate 1-2: Under nitrogen protection, Intermediate 1-1 (100.0 g, 0.49 mol), 3-chloro-2-fluorobromobenzene (104.9 g, 0.50 mol), tetrakis(triphenylphosphine)palladium (2.9 g, 2.5 mmol), potassium carbonate (102.4 g, 0.74 mol), tetrabutylammonium bromide (3.2 g, 9.9 mmol), toluene (1 L), ethanol (400 mL) and pure water (200 mL) were added to a three-necked flask. After replacing the reaction flask with nitrogen three times, the temperature was raised to 80 °C and reacted for 8 hours. After cooling the reaction solution to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 108.0 g of Intermediate 1-2, and the yield was 76.3%.

[0027] Synthesis of Intermediate 1-3: Intermediate 1-2 (100.0 g, 0.35 mol) and dichloromethane (1 L) were added to a dried three-necked flask. The reaction system was cooled to -5 to 0 °C using an ice-salt bath, boron tribromide (346.4 g, 1.4 mol) was added dropwise, and the mixture was stirred at room temperature for 6 hours. After the reaction, it was poured into ice water to quench the reaction. After separating the organic phase, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 82.8 g of Intermediate 1-3, with a yield of 87.1%.

[0028] Synthesis of Intermediate 1-4: Intermediate 1-3 (80.0 g, 0.29 mol), potassium carbonate (81.2 g, 0.59 mol), and N,N-dimethylformamide (1 L) were added to a dried three-necked flask, heated to 140 °C, and reacted for 2 hours. After the reaction solution was cooled to room temperature, it was poured into water under stirring conditions to precipitate a solid. After filtration, the filter cake was completely dissolved in toluene, then washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 63.7 g of Intermediate 1-4, with a yield of 85.9%.

[0029] Synthesis of Intermediate 1-5: Intermediate 1-4 (60.0 g, 238.1 mmol), bis(pinacolato)diboron (72.6 g, 285.7 mmol), 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium (1.7 g, 2.4 mmol), potassium acetate (35.0 g, 357.2 mmol), and toluene (800 mL) were added to a dried three-necked flask. After the reaction flask was replaced with nitrogen three times, it was heated to reflux and reacted for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 67.4 g of Intermediate 1-5, with a yield of 82.3%.

[0030] Synthesis of Intermediate 1-6: Under nitrogen protection, intermediate 1-5 (65.0 g, 188.9 mmol), methyl 2-bromo-4-chlorobenzoate (47.8 g, 192.6 mmol), tetrakis(triphenylphosphine)palladium (2.9 g, 1.9 mmol), potassium carbonate (39.1 g, 283.3 mmol), tetrabutylammonium bromide (1.2 g, 3.8 mmol), toluene (800 mL), ethanol (200 mL) and pure water (100 mL) were added to a three-necked flask. After the reaction flask was purged with nitrogen three times, the temperature was raised to 80 °C and the reaction was carried out for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 52.4 g of intermediate 1-6, with a yield of 71.9%.

[0031] Synthesis of intermediate 1-7: Under nitrogen protection, intermediate 1-6 (50.0 g, 129.5 mmol) and tetrahydrofuran (400 mL) were added to a three-necked flask. A 388.5 mL solution of methylmagnesium bromide in tetrahydrofuran with a concentration of 1.0 M was added dropwise under stirring at room temperature. After the addition was complete, the temperature was raised to 50 °C and the reaction was carried out for 3 hours. After the reaction solution was cooled to room temperature, an aqueous ammonium chloride solution was added to quench the reaction. After adjusting the pH to weakly acidic, it was washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 37.9 g of intermediate 1-7, with a yield of 75.8%.

[0032] Synthesis of intermediate 1-8: Under nitrogen protection, intermediate 1-7 (35.0 g, 90.6 mmol), methanesulfonic acid (17.4 g, 181.3 mmol) and toluene (300 mL) were added to a three-necked flask. The temperature was raised to 100 °C and the reaction was carried out for 3 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 27.2 g of intermediate 1-8, with a yield of 81.6%.

[0033] Synthesis of intermediate 1: Intermediate 1-8 (60.0 g, 238.1 mmol), bis(pinacolato)diboron (72.6 g, 285.7 mmol), 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium (1.7 g, 2.4 mmol), potassium acetate (35.0 g, 357.2 mmol) and toluene (800 mL) were added to a dried three-necked flask. After replacing the reaction flask with nitrogen three times, the temperature was raised to reflux and reacted for 8 hours. After cooling the reaction solution to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 67.4 g of Intermediate 1 with a yield of 77.5%.

[0034] Example 2 This example provides the synthesis of Intermediate 2. The synthesis route is as follows.

[0035]

Chemical Structure

[0036] Synthesis of Intermediate 2-2: Under nitrogen protection, Intermediate 2-1 (100.0 g, 0.49 mol), 3-chloro-2-fluorobromobenzene (104.9 g, 0.50 mol), tetrakis(triphenylphosphine)palladium (2.9 g, 2.5 mmol), potassium carbonate (102.4 g, 0.74 mol), tetrabutylammonium bromide (3.2 g, 9.9 mmol), toluene (1 L), ethanol (400 mL) and pure water (200 mL) were added to a three-necked flask. After replacing the reaction flask with nitrogen three times, the temperature was raised to 80 °C and reacted for 8 hours. After cooling the reaction solution to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 108.0 g of Intermediate 2-2 with a yield of 78.1%.

[0037] Synthesis of Intermediate 2-3: Intermediate 2-2 (100.0 g, 0.35 mol) and dichloromethane (1 L) were added to a dried three-necked flask. The reaction system was cooled to -5 to 0 °C using an ice-salt bath, and boron tribromide (346.4 g, 1.4 mol) was added dropwise. After reacting for 6 hours with stirring at room temperature, it was poured into ice water to quench the reaction. After separating the organic phase, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 82.8 g of Intermediate 2-3, with a yield of 71.2%.

[0038] Synthesis of Intermediate 2-4: Intermediate 2-3 (80.0 g, 0.29 mol), potassium carbonate (81.2 g, 0.59 mol), and N,N-dimethylformamide (1 L) were added to a dried three-necked flask, heated to 140 °C, and reacted for 2 hours. After cooling the reaction solution to room temperature, it was poured into water under stirring conditions to precipitate a solid. After filtration, the filter cake was completely dissolved in toluene, then washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 63.7 g of Intermediate 2-4, with a yield of 33.9%.

[0039] Synthesis of Intermediate 2-5: Intermediate 2-4 (60.0 g, 238.1 mmol), bis(pinacolato)diboron (72.6 g, 285.7 mmol), 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium (1.7 g, 2.4 mmol), potassium acetate (35.0 g, 357.2 mmol), and toluene (800 mL) were added to a dried three-necked flask. After replacing the reaction flask with nitrogen three times, it was heated to reflux and reacted for 8 hours. After cooling the reaction solution to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 67.4 g of Intermediate 2-5, with a yield of 77.6%.

[0040] Synthesis of Intermediate 2-6: Under nitrogen protection, intermediate 2-5 (65.0 g, 188.9 mmol), methyl 2-bromo-4-chlorobenzoate (47.8 g, 192.6 mmol), tetrakis(triphenylphosphine)palladium (2.9 g, 1.9 mmol), potassium carbonate (39.1 g, 283.3 mmol), tetrabutylammonium bromide (1.2 g, 3.8 mmol), toluene (800 mL), ethanol (200 mL) and pure water (100 mL) were added to a three-necked flask. After replacing the reaction flask with nitrogen three times, the temperature was raised to 80 °C and reacted for 8 hours. After cooling the reaction solution to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 52.4 g of intermediate 2-6, with a yield of 71.9%.

[0041] Synthesis of intermediate 2-7: Under nitrogen protection, intermediate 2-6 (50.0 g, 129.5 mmol) and tetrahydrofuran (400 mL) were added to a three-necked flask. A 388.5 mL solution of methylmagnesium bromide in tetrahydrofuran with a concentration of 1.0 M was added dropwise under stirring at room temperature. After the addition was completed, the temperature was raised to 50 °C and reacted for 3 hours. After cooling the reaction solution to room temperature, an aqueous ammonium chloride solution was added to quench the reaction. After adjusting the pH to weakly acidic, it was washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 37.9 g of intermediate 2-7, with a yield of 83.1%.

[0042] Synthesis of intermediate 2-8: Under nitrogen protection, intermediate 2-7 (35.0 g, 90.6 mmol), methanesulfonic acid (17.4 g, 181.3 mmol) and toluene (300 mL) were added to a three-necked flask. The temperature was raised to 100 °C and reacted for 3 hours. After cooling the reaction solution to room temperature, it was washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 27.2 g of intermediate 2-8, with a yield of 79.7%.

[0043] Synthesis of intermediate 2: Intermediate 2-8 (60.0 g, 238.1 mmol), bis(pinacolato)diboron (72.6 g, 285.7 mmol), 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium (1.7 g, 2.4 mmol), potassium acetate (35.0 g, 357.2 mmol) and toluene (800 mL) were added to a dried three-necked flask. After replacing the reaction flask with nitrogen three times, the temperature was raised to reflux and reacted for 8 hours. After cooling the reaction solution to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 67.4 g of Intermediate 2 with a yield of 82.3%.

[0044] Example 3 This example provides the synthesis of Intermediate 3. The synthetic route is as follows.

[0045]

Chemical formula

[0046] Synthesis of Intermediate 3-1: Under nitrogen protection, Intermediate 1-1 (100.0 g, 0.49 mol), 3-chloro-2,4-difluorobromobenzene (104.9 g, 0.50 mol), tetrakis(triphenylphosphine)palladium (2.9 g, 2.5 mmol), potassium carbonate (102.4 g, 0.74 mol), tetrabutylammonium bromide (3.2 g, 9.9 mmol), toluene (1 L), ethanol (400 mL) and pure water (200 mL) were added to a three-necked flask. After replacing the reaction flask with nitrogen three times, the temperature was raised to 80 °C and reacted for 8 hours. After cooling the reaction solution to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 108.0 g of Intermediate 3-1 with a yield of 69.7%.

[0047] Synthesis of Intermediate 3-2: Intermediate 3-1 (100.0 g, 0.35 mol) and dichloromethane (1 L) were added to a dried three-necked flask. The reaction system was cooled to -5 to 0 °C using an ice-salt bath. Boron tribromide (346.4 g, 1.4 mol) was added dropwise, and the mixture was stirred at room temperature for 6 hours. After the reaction, it was poured into ice water to quench the reaction. After separating the organic phase, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 82.8 g of Intermediate 3-2, with a yield of 86.1%.

[0048] Synthesis of Intermediate 3-3: Intermediate 3-2 (80.0 g, 0.29 mol), potassium carbonate (81.2 g, 0.59 mol), and N,N-dimethylformamide (1 L) were added to a dried three-necked flask. The temperature was raised to 140 °C and the reaction was carried out for 2 hours. After the reaction solution was cooled to room temperature, it was poured into water under stirring conditions to precipitate a solid. After filtration, the filter cake was completely dissolved in toluene, and then washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 63.7 g of Intermediate 3-3, with a yield of 83.7%.

[0049] Synthesis of Intermediate 3-4: Intermediate 3-3 (60.0 g, 238.1 mmol), bis(pinacolato)diboron (72.6 g, 285.7 mmol), 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium (1.7 g, 2.4 mmol), potassium acetate (35.0 g, 357.2 mmol), and toluene (800 mL) were added to a dried three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to reflux and the reaction was carried out for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 67.4 g of Intermediate 3-4, with a yield of 85.2%.

[0050] Synthesis of Intermediate 3-5: Under nitrogen protection, intermediate 3-4 (65.0 g, 188.9 mmol), 2-bromo-4-chloroanisole (47.8 g, 192.6 mmol), tetrakis(triphenylphosphine)palladium (2.9 g, 1.9 mmol), potassium carbonate (39.1 g, 283.3 mmol), tetrabutylammonium bromide (1.2 g, 3.8 mmol), toluene (800 mL), ethanol (200 mL) and pure water (100 mL) were added to a three-necked flask. After replacing the reaction flask with nitrogen three times, the temperature was raised to 80 °C and reacted for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 52.4 g of intermediate 3-5, with a yield of 73.6%.

[0051] Synthesis of intermediate 3-6: Intermediate 3-5 (100.0 g, 0.35 mol) and dichloromethane (1 L) were added to a dried three-necked flask. The reaction system was cooled to -5 to 0 °C using an ice-salt bath, boron tribromide (346.4 g, 1.4 mol) was added dropwise, and after stirring at room temperature for 6 hours, it was poured into ice water to quench the reaction. After separating the organic phase, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 82.8 g of intermediate 3-6, with a yield of 82.9%.

[0052] Synthesis of intermediate 3-7: Intermediate 3-6 (80.0 g, 0.29 mol), potassium carbonate (81.2 g, 0.59 mol) and N,N-dimethylformamide (1 L) were added to a dried three-necked flask. The temperature was raised to 140 °C and reacted for 2 hours. After the reaction solution was cooled to room temperature, it was poured into water under stirring conditions to precipitate a solid. After filtration, the filter cake was completely dissolved in toluene, then washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 63.7 g of intermediate 3-7, with a yield of 87.2%.

[0053] Synthesis of intermediate 3: Intermediate 3-7 (60.0 g, 238.1 mmol), bis(pinacolato)diboron (72.6 g, 285.7 mmol), 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium (1.7 g, 2.4 mmol), potassium acetate (35.0 g, 357.2 mmol) and toluene (800 mL) were added to a dried three-necked flask, and the reaction flask was replaced with nitrogen three times. Then, the temperature was raised to reflux and the reaction was carried out for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 67.4 g of Intermediate 3 with a yield of 72.9%.

[0054] Example 4 This example provides the synthesis of Intermediate 4. The synthetic route is as follows.

[0055]

Chemical Structure

[0056] Synthesis of Intermediate 4-1: Under nitrogen protection, Intermediate 3-4 (65.0 g, 188.9 mmol), 2-bromo-4-chlorothioanisole (47.8 g, 192.6 mmol), tetrakis(triphenylphosphine)palladium (2.9 g, 1.9 mmol), potassium carbonate (39.1 g, 283.3 mmol), tetrabutylammonium bromide (1.2 g, 3.8 mmol), toluene (800 mL), ethanol (200 mL) and pure water (100 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to 80 °C and the reaction was carried out for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 52.4 g of Intermediate 4-1 with a yield of 73.5%.

[0057] Synthesis of Intermediate 4-2: Intermediate 4-1 (100.0 g, 0.35 mol) and dichloromethane (1 L) were added to a dried three-necked flask. The reaction system was cooled to -5 to 0 °C using an ice-salt bath. Boron tribromide (346.4 g, 1.4 mol) was added dropwise, and the mixture was stirred at room temperature for 6 hours. Then, it was poured into ice water to quench the reaction. After separating the organic phase, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 82.8 g of Intermediate 4-2, with a yield of 82.7%.

[0058] Synthesis of Intermediate 4-3: Intermediate 4-2 (80.0 g, 0.29 mol), potassium carbonate (81.2 g, 0.59 mol), and N,N-dimethylformamide (1 L) were added to a dried three-necked flask. The temperature was raised to 140 °C and the reaction was carried out for 2 hours. After cooling the reaction solution to room temperature, it was poured into water under stirring conditions to precipitate a solid. After filtration, the filter cake was completely dissolved in toluene, and then washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 63.7 g of Intermediate 4-3, with a yield of 80.6%.

[0059] Synthesis of Intermediate 4: Intermediate 4-3 (60.0 g, 238.1 mmol), bis(pinacolato)diboron (72.6 g, 285.7 mmol), 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium (1.7 g, 2.4 mmol), potassium acetate (35.0 g, 357.2 mmol), and toluene (800 mL) were added to a dried three-necked flask. After replacing the reaction flask with nitrogen three times, the temperature was raised to reflux and the reaction was carried out for 8 hours. After cooling the reaction solution to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 67.4 g of Intermediate 4, with a yield of 75.8%.

[0060] Example 5 This example provides the synthesis of Intermediate 5. The synthesis route is as follows.

[0061] [Chemistry]

[0062] Synthesis of Intermediate 5-2: Under nitrogen protection, Intermediate 5-1 (100.0 g, 0.49 mol), 3-chloro-2-fluorobromobenzene (104.9 g, 0.50 mol), tetrakis(triphenylphosphine)palladium (2.9 g, 2.5 mmol), potassium carbonate (102.4 g, 0.74 mol), tetrabutylammonium bromide (3.2 g, 9.9 mmol), toluene (1 L), ethanol (400 mL) and pure water (200 mL) were added to a three-necked flask. After replacing the reaction flask with nitrogen three times, the temperature was raised to 80 °C and reacted for 8 hours. After cooling the reaction solution to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 108.0 g of Intermediate 5-2, with a yield of 70.6%.

[0063] Synthesis of Intermediate 5-3: Intermediate 5-2 (100.0 g, 0.35 mol) and dichloromethane (1 L) were added to a dried three-necked flask. The reaction system was cooled to -5 to 0 °C using an ice-salt bath, boron tribromide (346.4 g, 1.4 mol) was added dropwise, and after stirring at room temperature for 6 hours, it was poured into ice water to quench the reaction. After separating the organic phase, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 82.8 g of Intermediate 5-3, with a yield of 85.3%.

[0064] Synthesis of Intermediate 5-4: Intermediate 5-3 (80.0 g, 0.29 mol), potassium carbonate (81.2 g, 0.59 mol), and N,N-dimethylformamide (1 L) were added to a dried three-necked flask, heated to 140 °C, and reacted for 2 hours. After the reaction solution was cooled to room temperature, it was poured into water under stirring conditions to precipitate a solid. After filtration, the filter cake was completely dissolved in toluene, then washed with water until neutral, the organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 63.7 g of Intermediate 5-4, with a yield of 81.7%.

[0065] Synthesis of Intermediate 5-5: Intermediate 5-4 (60.0 g, 238.1 mmol), bis(pinacolato)diboron (72.6 g, 285.7 mmol), 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium (1.7 g, 2.4 mmol), potassium acetate (35.0 g, 357.2 mmol), and toluene (800 mL) were added to a dried three-necked flask. After the reaction flask was replaced with nitrogen three times, it was heated to reflux and reacted for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 67.4 g of Intermediate 5-5, with a yield of 84.2%.

[0066] Synthesis of Intermediate 5-6: Under nitrogen protection, Intermediate 5-5 (65.0 g, 188.9 mmol), methyl 2-bromo-4-chlorobenzoate (47.8 g, 192.6 mmol), tetrakis(triphenylphosphine)palladium (2.9 g, 1.9 mmol), potassium carbonate (39.1 g, 283.3 mmol), tetrabutylammonium bromide (1.2 g, 3.8 mmol), toluene (800 mL), ethanol (200 mL), and pure water (100 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, it was heated to 80 °C and reacted for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 52.4 g of Intermediate 5-6, with a yield of 72.1%.

[0067] Synthesis of Intermediate 5-7: Under nitrogen protection, Intermediate 5-6 (50.0 g, 129.5 mmol) and tetrahydrofuran (400 mL) were added to a three-necked flask. A solution of methylmagnesium bromide in tetrahydrofuran with a concentration of 1.0 M (388.5 mL) was added dropwise under stirring at room temperature. After the addition was complete, the temperature was raised to 50 °C and the reaction was carried out for 3 hours. After the reaction solution was cooled to room temperature, an aqueous ammonium chloride solution was added to quench the reaction. After adjusting the pH to weakly acidic, it was washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 37.9 g of Intermediate 5-7, with a yield of 76.8%.

[0068] Synthesis of Intermediate 5-8: Under nitrogen protection, Intermediate 5-7 (35.0 g, 90.6 mmol), methanesulfonic acid (17.4 g, 181.3 mmol) and toluene (300 mL) were added to a three-necked flask. The temperature was raised to 100 °C and the reaction was carried out for 3 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 27.2 g of Intermediate 5-8, with a yield of 83.3%.

[0069] Synthesis of Intermediate 5: Intermediate 5-8 (60.0 g, 238.1 mmol), bis(pinacolato)diboron (72.6 g, 285.7 mmol), 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium (1.7 g, 2.4 mmol), potassium acetate (35.0 g, 357.2 mmol) and toluene (800 mL) were added to a dried three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to reflux and the reaction was carried out for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 67.4 g of Intermediate 5, with a yield of 76.4%.

[0070] Example 6 This example provides the synthesis of Intermediate 6. The synthesis route is as follows.

[0071]

Chem.

[0072] Synthesis of Intermediate 6-1: Under nitrogen protection, Intermediate 2-1 (100.0 g, 0.49 mol), 3-chlorobromobenzene (104.9 g, 0.50 mol), tetrakis(triphenylphosphine)palladium (2.9 g, 2.5 mmol), potassium carbonate (102.4 g, 0.74 mol), tetrabutylammonium bromide (3.2 g, 9.9 mmol), toluene (1 L), ethanol (400 mL) and pure water (200 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to 80 °C and the reaction was carried out for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 108.0 g of Intermediate 6-1, and the yield was 74.9%.

[0073] Synthesis of Intermediate 6-2: Under nitrogen protection, Intermediate 6-1 (50.0 g, 129.5 mmol) and tetrahydrofuran (400 mL) were added to a three-necked flask. Under stirring conditions at room temperature, 388.5 mL of a 1.0 M tetrahydrofuran solution of methylmagnesium bromide was added dropwise. After the addition was complete, the temperature was raised to 50 °C and the reaction was carried out for 3 hours. After the reaction solution was cooled to room temperature, an aqueous ammonium chloride solution was added to quench the reaction. After adjusting the pH to weakly acidic, it was washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 37.9 g of Intermediate 6-2, and the yield was 76.3%.

[0074] Synthesis of Intermediate 6-3: Under nitrogen protection, intermediate 6-2 (35.0 g, 90.6 mmol), methanesulfonic acid (17.4 g, 181.3 mmol) and toluene (300 mL) were added to a three-necked flask, heated to 100 °C and reacted for 3 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, the organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 27.2 g of intermediate 6-3, with a yield of 42.1%.

[0075] Synthesis of intermediate 6-4: Intermediate 6-3 (60.0 g, 238.1 mmol), bis(pinacolato)diboron (72.6 g, 285.7 mmol), 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium (1.7 g, 2.4 mmol), potassium acetate (35.0 g, 357.2 mmol) and toluene (800 mL) were added to a dried three-necked flask. After the reaction flask was replaced with nitrogen three times, it was heated to reflux and reacted for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 67.4 g of intermediate 6-4, with a yield of 82.7%.

[0076] Synthesis of intermediate 6-5: Under nitrogen protection, intermediate 6-4 (65.0 g, 188.9 mmol), methyl 2-bromo-4-chlorobenzoate (47.8 g, 192.6 mmol), tetrakis(triphenylphosphine)palladium (2.9 g, 1.9 mmol), potassium carbonate (39.1 g, 283.3 mmol), tetrabutylammonium bromide (1.2 g, 3.8 mmol), toluene (800 mL), ethanol (200 mL) and pure water (100 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, it was heated to 80 °C and reacted for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 52.4 g of intermediate 6-5, with a yield of 78.4%.

[0077] Synthesis of intermediate 6-6: Under nitrogen protection, intermediate 6-5 (50.0 g, 129.5 mmol) and tetrahydrofuran (400 mL) were added to a three-necked flask, and 388.5 mL of a tetrahydrofuran solution of phenylmagnesium bromide with a concentration of 1.0 M was added dropwise under stirring at room temperature. After the addition was completed, the temperature was raised to 50 °C and the reaction was carried out for 3 hours. After the reaction solution was cooled to room temperature, an aqueous ammonium chloride solution was added to quench the reaction, and after adjusting the pH to weakly acidic, it was washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 37.9 g of intermediate 6-6, and the yield was 68.2%.

[0078] Synthesis of intermediate 6-7: Under nitrogen protection, intermediate 6-6 (35.0 g, 90.6 mmol), trifluoromethanesulfonic acid (17.4 g, 181.3 mmol) and toluene (300 mL) were added to a three-necked flask, the temperature was raised to 100 °C, and the reaction was carried out for 3 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 27.2 g of intermediate 6-7, and the yield was 76.7%.

[0079] Synthesis of intermediate 6: Intermediate 6-7 (60.0 g, 238.1 mmol), bis(pinacolato)diboron (72.6 g, 285.7 mmol), 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium (1.7 g, 2.4 mmol), potassium acetate (35.0 g, 357.2 mmol) and toluene (800 mL) were added to a dried three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to reflux and the reaction was carried out for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 67.4 g of intermediate 6, and the yield was 79.6%.

[0080] Example 7 This example provides the synthesis of intermediate 7. The synthesis route is as follows.

[0081] [Chemistry]

[0082] Synthesis of Intermediate 7-1: Under nitrogen protection, Intermediate 5-1 (100.0 g, 0.49 mol), 3-chloro-2,4-difluorobromobenzene (104.9 g, 0.50 mol), tetrakis(triphenylphosphine)palladium (2.9 g, 2.5 mmol), potassium carbonate (102.4 g, 0.74 mol), tetrabutylammonium bromide (3.2 g, 9.9 mmol), toluene (1 L), ethanol (400 mL) and pure water (200 mL) were added to a three-necked flask. After replacing the reaction flask with nitrogen three times, the temperature was raised to 80 °C and reacted for 8 hours. After cooling the reaction solution to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 108.0 g of Intermediate 7-1, with a yield of 75.2%.

[0083] Synthesis of Intermediate 7-2: Intermediate 7-1 (100.0 g, 0.35 mol) and dichloromethane (1 L) were added to a dried three-necked flask. Using an ice-salt bath, the reaction system was cooled to -5~0 °C, boron tribromide (346.4 g, 1.4 mol) was added dropwise, and after stirring at room temperature for 6 hours, it was poured into ice water to quench the reaction. After separating the organic phase, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 82.8 g of Intermediate 7-2, with a yield of 80.5%.

[0084] Synthesis of Intermediate 7-3: Intermediate 7-2 (80.0 g, 0.29 mol), potassium carbonate (81.2 g, 0.59 mol), and N,N-dimethylformamide (1 L) were added to a dried three-necked flask, heated to 140 °C, and reacted for 2 hours. After the reaction solution was cooled to room temperature, it was poured into water under stirring conditions to precipitate a solid. After filtration, the filter cake was completely dissolved in toluene, then washed with water until neutral, the organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 63.7 g of Intermediate 7-3, with a yield of 86.6%.

[0085] Synthesis of Intermediate 7-4: Intermediate 7-3 (60.0 g, 238.1 mmol), bis(pinacolato)diboron (72.6 g, 285.7 mmol), 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium (1.7 g, 2.4 mmol), potassium acetate (35.0 g, 357.2 mmol), and toluene (800 mL) were added to a dried three-necked flask. After the reaction flask was replaced with nitrogen three times, it was heated to reflux and reacted for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 67.4 g of Intermediate 7-4, with a yield of 82.6%.

[0086] Synthesis of Intermediate 7-5: Under nitrogen protection, Intermediate 7-4 (65.0 g, 188.9 mmol), 2-bromo-4-chloroanisole (47.8 g, 192.6 mmol), tetrakis(triphenylphosphine)palladium (2.9 g, 1.9 mmol), potassium carbonate (39.1 g, 283.3 mmol), tetrabutylammonium bromide (1.2 g, 3.8 mmol), toluene (800 mL), ethanol (200 mL), and pure water (100 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, it was heated to 80 °C and reacted for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 52.4 g of Intermediate 7-5, with a yield of 72.3%.

[0087] Synthesis of Intermediate 7-6: Intermediate 7-5 (100.0 g, 0.35 mol) and dichloromethane (1 L) were added to a dried three-necked flask. The reaction system was cooled to -5 to 0 °C using an ice-salt bath, and boron tribromide (346.4 g, 1.4 mol) was added dropwise. After stirring at room temperature for 6 hours, the reaction was quenched by pouring it into ice water. After separating the organic phase, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 82.8 g of Intermediate 7-6, with a yield of 85.9%.

[0088] Synthesis of Intermediate 7-7: Intermediate 7-6 (80.0 g, 0.29 mol), potassium carbonate (81.2 g, 0.59 mol), and N,N-dimethylformamide (1 L) were added to a dried three-necked flask. The temperature was raised to 140 °C and the reaction was carried out for 2 hours. After cooling the reaction solution to room temperature, it was poured into water under stirring conditions to precipitate a solid. After filtration, the filter cake was completely dissolved in toluene, and then washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 63.7 g of Intermediate 7-7, with a yield of 83.4%.

[0089] Synthesis of Intermediate 7: Intermediate 7-7 (60.0 g, 238.1 mmol), bis(pinacolato)diboron (72.6 g, 285.7 mmol), 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium (1.7 g, 2.4 mmol), potassium acetate (35.0 g, 357.2 mmol), and toluene (800 mL) were added to a dried three-necked flask. After replacing the reaction flask with nitrogen three times, the temperature was raised to reflux and the reaction was carried out for 8 hours. After cooling the reaction solution to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 67.4 g of Intermediate 7, with a yield of 73.8%.

[0090] Example 8 This example provides the synthesis of Intermediate 8. The synthesis route is as follows.

[0091]

Chem.

[0092] Synthesis of Intermediate 8-1: Under nitrogen protection, intermediate 7-4 (65.0 g, 188.9 mmol), 2-bromo-4-chlorothioanisole (47.8 g, 192.6 mmol), tetrakis(triphenylphosphine)palladium (2.9 g, 1.9 mmol), potassium carbonate (39.1 g, 283.3 mmol), tetrabutylammonium bromide (1.2 g, 3.8 mmol), toluene (800 mL), ethanol (200 mL) and pure water (100 mL) were added to a three-necked flask. After replacing the reaction flask with nitrogen three times, the temperature was raised to 80 °C and reacted for 8 hours. After cooling the reaction solution to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 52.4 g of intermediate 8-1, with a yield of 71.9%.

[0093] Synthesis of Intermediate 8-2: Intermediate 8-1 (100.0 g, 0.35 mol) and dichloromethane (1 L) were added to a dried three-necked flask. The reaction system was cooled to -5 to 0 °C using an ice-salt bath, boron tribromide (346.4 g, 1.4 mol) was added dropwise, and stirred at room temperature for 6 hours. Then it was poured into ice water to quench the reaction. After separating the organic phase, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 82.8 g of intermediate 8-2, with a yield of 82.2%.

[0094] Synthesis of Intermediate 8-3: Intermediate 8-2 (80.0 g, 0.29 mol), potassium carbonate (81.2 g, 0.59 mol), and N,N-dimethylformamide (1 L) were added to a dried three-necked flask, heated to 140 °C, and reacted for 2 hours. After the reaction solution was cooled to room temperature, it was poured into water under stirring conditions to precipitate a solid. After filtration, the filter cake was completely dissolved in toluene, then washed with water until neutral. The organic phase was dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 63.7 g of Intermediate 8-3, with a yield of 75.3%.

[0095] Synthesis of Intermediate 8: Intermediate 8-3 (60.0 g, 238.1 mmol), bis(pinacolato)diboron (72.6 g, 285.7 mmol), 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium (1.7 g, 2.4 mmol), potassium acetate (35.0 g, 357.2 mmol), and toluene (800 mL) were added to a dried three-necked flask. After the reaction flask was replaced with nitrogen three times, it was heated to reflux and reacted for 8 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and purified through a silica gel column to obtain 67.4 g of Intermediate 8, with a yield of 83.6%.

[0096] Example 9 This example provides the synthesis of Compound 3. The synthetic route is as follows.

[0097]

Chemical Structure

[0098] Under nitrogen protection, intermediate 1 (10.0 g, 21.7 mmol), 1-bromopyrene (6.4 g, 22.8 mmol), tetrakis(triphenylphosphine)palladium (0.25 g, 0.22 mmol), potassium carbonate (6.0 g, 43.4 mmol), tetrabutylammonium bromide (0.70 g, 2.17 mmol), toluene (200 mL), ethanol (60 mL) and pure water (30 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to 80 °C and the reaction was carried out for 6 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and recrystallized and purified by toluene / ethanol recrystallization (volume ratio 2:1) to obtain 8.4 g of compound 3 with a yield of 72.8%.

[0099] The mass spectrometry detection result of the obtained compound 3 was HR-MS(APCI): m / z = 535.1984 [M+H] + ; C 41 H 26 The calculated values for C, H, and O were: C, 92.1058; H, 4.9018; O, 2.9924; the measured values were: C, 92.1071; H, 4.9008; O, 2.9921.

[0100] Example 10 This example provides the synthesis of compound 14. The synthetic route is as follows.

[0101]

Chemical formula

[0102] Under nitrogen protection, intermediate 2 (10.0 g, 21.0 mmol), 1-bromopyrene (6.2 g, 22.0 mmol), tetrakis(triphenylphosphine)palladium (0.24 g, 0.21 mmol), potassium carbonate (5.8 g, 42.0 mmol), tetrabutylammonium bromide (0.68 g, 2.1 mmol), toluene (200 mL), ethanol (60 mL) and pure water (30 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to 80 °C and reacted for 6 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and recrystallized by toluene / ethanol recrystallization (volume ratio 2:1) to obtain 7.9 g of compound 14 with a yield of 68.3%.

[0103] The mass spectrometry detection result of the obtained compound 14 was HR-MS(APCI): m / z = 551.1755[M+H] + ;C 41 H 26 The calculated values for C, H, and S were: C, 89.4196; H, 4.7589; S, 5.8215; the measured values were: C, 89.4217; H, 4.7578; S, 5.8205.

[0104] Example 11 This example provides the synthesis of compound 71. The synthetic route is as follows.

[0105]

Chemical formula

[0106] Under nitrogen protection, intermediate 3 (10.0 g, 23.0 mmol), 8-bromophenanthro[4,5-bcd]furan (6.5 g, 24.2 mmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.23 mmol), potassium carbonate (6.3 g, 46.0 mmol), tetrabutylammonium bromide (0.74 g, 2.3 mmol), toluene (200 mL), ethanol (60 mL), and pure water (30 mL) were added to a three-necked flask. After replacing the reaction flask with nitrogen three times, the temperature was raised to 80 °C and the reaction was carried out for 6 hours. After cooling the reaction solution to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and recrystallized and purified by toluene / ethanol recrystallization (volume ratio 2:1) to obtain 7.7 g of compound 71, with a yield of 67.1%.

[0107] The mass spectrometry detection result of the obtained compound 71 was HR-MS(APCI): m / z = 499.1256 [M+H] + ;C 36 H 18 The calculated values of C, H, and O3 (%) were: C, 86.7330; H, 3.6394; O, 9.6276; the measured values were: C, 86.7346; H, 3.6387; O, 9.6267.

[0108] Example 12 This example provides the synthesis of compound 72. The synthesis route is as follows.

[0109]

Chemical formula

[0110] Under nitrogen protection, intermediate 4 (10.0 g, 22.2 mmol), 8-bromophenanthro[4,5-bcd]furan (6.3 g, 23.3 mmol), tetrakis(triphenylphosphine)palladium (0.26 g, 0.22 mmol), potassium carbonate (6.1 g, 44.4 mmol), tetrabutylammonium bromide (0.72 g, 2.22 mmol), toluene (200 mL), ethanol (60 mL) and pure water (30 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to 80 °C and reacted for 6 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and recrystallized and purified by toluene / ethanol recrystallization (volume ratio 2:1) to obtain 8.1 g of compound 72, and the yield was 70.8%.

[0111] The mass spectrometry detection result of the obtained compound 72 was HR-MS(APCI): m / z = 515.1028 [M+H] + ;C 36 H 18 The calculated values for C, H, and O2S were: C, 84.0260; H, 3.5259; O, 6.2181; the measured values were: C, 884.0273; H, 3.5251; O, 6.2177.

[0112] Example 13 This example provides the synthesis of compound 80. The synthetic route is as follows.

[0113]

Chemical formula

[0114] Under nitrogen protection, intermediate 4 (10.0 g, 22.2 mmol), 10-bromo-7-oxabenz[de]anthracene (6.9 g, 23.3 mmol), tetrakis(triphenylphosphine)palladium (0.26 g, 0.22 mmol), potassium carbonate (6.1 g, 44.4 mmol), tetrabutylammonium bromide (0.72 g, 2.22 mmol), toluene (200 mL), ethanol (60 mL) and pure water (30 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to 80 °C and reacted for 6 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and recrystallized and purified by toluene / ethanol recrystallization (volume ratio 2:1) to obtain 9.0 g of compound 80, and the yield was 75.2%.

[0115] The mass spectrometry detection result of the obtained compound 80 was HR-MS (APCI): m / z = 541.1184 = [M+H] + ; C 38 H 20 The calculated values for C, H, O2S were: C, 84.4224; H, 3.7289; O, 5.9186; S, 5.9301; the measured values were: C, 84.4261; H, 3.7276; O, 5.9179; S, 5.9284.

[0116] Example 14 This example provides the synthesis of compound 105. The synthetic route is as follows.

[0117]

Chemical formula

[0118] Under nitrogen protection, intermediate 4 (10.0 g, 21.0 mmol), 3-(10-bromo-9-anthracenyl)-9-phenyl-9H-carbazole (11.0 g, 22.0 mmol), tetrakis(triphenylphosphine)palladium (0.24 g, 0.21 mmol), potassium carbonate (5.8 g, 42.0 mmol), tetrabutylammonium bromide (0.68 g, 2.1 mmol), toluene (200 mL), ethanol (60 mL) and pure water (30 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to 80 °C and reacted for 6 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and recrystallized and purified by toluene / ethanol recrystallization (volume ratio 2:1) to obtain 11.2 g of compound 109, and the yield was 69.7%.

[0119] The mass spectrometry detection result of the obtained compound 105 was HR-MS(APCI): m / z = 768.2647[M+H] + ;C 57 H 37 The calculated values of C, H, N, and S were C, 89.1453; H, 4.8563; N, 1.8239; S, 4.1745; the measured values were C, 89.1476; H, 4.8529; N, 1.8247; S, 4.1748.

[0120] Example 15 This example provides the synthesis of compound 127. The synthetic route is as follows.

[0121]

Chemical formula

[0122] Under nitrogen protection, intermediate 3 (10.0 g, 23.0 mmol), 9-bromo-10-deuterated phenylanthracene (7.9 g, 24.2 mmol), tetrakis(triphenylphosphine)palladium (0.27 g, 0.23 mmol), potassium carbonate (6.3 g, 46.0 mmol), tetrabutylammonium bromide (0.74 g, 2.3 mmol), toluene (200 mL), ethanol (60 mL) and pure water (30 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to 80 °C and reacted for 6 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and recrystallized and purified by toluene / ethanol recrystallization (volume ratio 2:1) to obtain 9.3 g of compound 127, and the yield was 73.2%.

[0123] The mass spectrometry detection result of the obtained compound 127 was HR-MS (APCI): m / z = 566.1385 = [M + H] + ; C 42 H 19 The calculated values for C, H, O2D5 were: C, 89.1873; H, 5.1555; O, 5.6572; the measured values were: C, 89.1891; H, 5.1524; O, 5.6585.

[0124] Example 16 This example provides the synthesis of compound 142. The synthetic route is as follows.

[0125]

Chemical formula

[0126] Under nitrogen protection, intermediate 6 (10.0 g, 16.4 mmol), 1-bromopyrene-d (4.8 g, 17.2 mmol), tetrakis(triphenylphosphine)palladium (0.19 g, 0.16 mmol), potassium carbonate (4.5 g, 32.8 mmol), tetrabutylammonium bromide (0.52 g, 1.6 mmol), toluene (200 mL), ethanol (60 mL) and pure water (30 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to 80 °C and reacted for 6 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and recrystallized and purified by toluene / ethanol recrystallization (volume ratio 2:1) to obtain 7.4 g of compound 142, and the yield was 65.9%.

[0127] The mass spectrometry detection result of the obtained compound 142 was HR-MS(APCI): m / z = 696.2269 [M+H] + ; C 54 H 29 The calculated values for C9H9D9 were: C, 93.2100; H, 6.7900; the measured values were: C, 93.2153; H, 6.7847.

[0128] Example 17 This example provides the synthesis of compound 159. The synthetic route is as follows.

[0129]

Chemical Structure

[0130] Under nitrogen protection, intermediate 7 (10.0 g, 22.2 mmol), 8-bromodeuterated phenanthro[4,5-bcd]furan (6.3 g, 23.3 mmol), tetrakis(triphenylphosphine)palladium (0.26 g, 0.22 mmol), potassium carbonate (6.1 g, 44.4 mmol), tetrabutylammonium bromide (0.72 g, 2.22 mmol), toluene (200 mL), ethanol (60 mL) and pure water (30 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to 80 °C and the reaction was carried out for 6 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and recrystallized and purified by toluene / ethanol recrystallization (volume ratio 2:1) to obtain 7.3 g of compound 159, and the yield was 63.9%.

[0131] The mass spectrometry detection result of the obtained compound 159 was HR-MS(APCI): m / z = 522.0480 [M+H] + ;C 36 H 11 Calculated values for C35H32O2SD7: C, 82.9050; H, 4.8128; O, 6.1351; S, 6.1471; Measured values: C, 82.9067; H, 4.8093; O, 6.1362; S, 6.1478.

[0132] Example 18 This example provides the synthesis of compound 160. The synthetic route is as follows.

[0133]

Chemical Structure

[0134] Under nitrogen protection, intermediate 8 (10.0 g, 21.4 mmol), 1-bromopyrene-d (6.3 g, 22.5 mmol), tetrakis(triphenylphosphine)palladium (0.25 g, 0.21 mmol), potassium carbonate (5.9 g, 42.8 mmol), tetrabutylammonium bromide (0.69 g, 2.14 mmol), toluene (200 mL), ethanol (60 mL) and pure water (30 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to 80 °C and the reaction was carried out for 6 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and recrystallized and purified by toluene / ethanol recrystallization (volume ratio 2:1) to obtain 7.8 g of compound 160, and the yield was 67.2%.

[0135] The mass spectrometry detection result of the obtained compound 160 was HR-MS(APCI): m / z = 550.0302 [M+H] + ;C 38 H 11 The calculated values for C, H, S2D9 were: C, 83.0385; H, 5.2958; S, 11.6657; the measured values were: C, 83.0399; H, 5.2926; S, 11.6675.

[0136] Example 19 This example provides the synthesis of compound 161. The synthetic route is as follows.

[0137]

Chemical Structure

[0138] Under nitrogen protection, intermediate 5 (10.0 g, 21.0 mmol), 4-bromo-deuterated-7-oxabenz [d] anthracene (6.5 g, 22.0 mmol), tetrakis (triphenylphosphine) palladium (0.24 g, 0.21 mmol)), potassium carbonate (5.8 g, 42.0 mmol), tetrabutylammonium bromide (0.68 g, 2.1 mmol), toluene (200 mL), ethanol (60 mL) and pure water (30 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to 80 °C and reacted for 6 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and recrystallized by toluene / ethanol recrystallization (volume ratio 2:1) to obtain 8.1 g of compound 161, and the yield was 68.5%.

[0139] The mass spectrometry detection result of the obtained compound 161 was HR-MS (APCI): m / z = 576.1000 [M+H] + ;C 41 H 17 O S The calculated values of C, H, O, and D9 were: C, 85.5449; H, 6.1066; O, 2.7792; S, 5.5693; the measured values were: C, 85.5473; H, 6.1035; O, 2.7826; S, 5.5666.

[0140] Example 20 This example provides the synthesis of compound 165. The synthetic route is as follows.

[0141]

Chemical formula

[0142] Under nitrogen protection, intermediate 1 (10.0 g, 21.7 mmol), 8-bromodeuterated phenanthro[4,5-bcd]furan (6.2 g, 22.8 mmol), tetrakis(triphenylphosphine)palladium (0.25 g, 0.22 mmol), potassium carbonate (6.0 g, 43.4 mmol), tetrabutylammonium bromide (0.70 g, 2.17 mmol), toluene (200 mL), ethanol (60 mL) and pure water (30 mL) were added to a three-necked flask. After the reaction flask was replaced with nitrogen three times, the temperature was raised to 80 °C and reacted for 6 hours. After the reaction solution was cooled to room temperature, it was washed with water until neutral, dried over anhydrous sodium sulfate, concentrated, and recrystallized and purified by toluene / ethanol recrystallization (volume ratio 2:1) to obtain 7.1 g of compound 165, and the yield was 62.7%.

[0143] The mass spectrometry detection result of the obtained compound 165 sample was HR-MS (APCI): m / z = 532.1229 [M+H] + ; C 39 H 17 Calculated values for C8H5O2D7:: C, 88.1210; H, 5.8596; O, 6.0194; Found: C, 88.1257; H, 5.8530; O, 6.0213.

[0144] Other compounds disclosed in the present invention, excluding compound 3, compound 14, compound 71, compound 72, compound 80, compound 105, compound 131, compound 142, compound 159, compound 160, compound 161 and compound 165, can also be prepared with reference to the above synthetic method.

[0145] Example 21 This example provides the T1 energy level, HOMO, and LUMO simulation calculations for Compound 3, Compound 14, Compound 71, Compound 72, Compound 80, Compound 105, Compound 131, Compound 142, Compound 159, Compound 160, Compound 161, Compound 165, and the existing light-emitting layer host material BH1. HOMO and LUMO are data obtained from simulation calculations. The calculation method uses the B3LYP hybrid functional, and the basis function set is 6-31g(d,P). The results are shown in Table 1.

[0146] Table 1 Simulation calculation results of T1 energy level, HOMO, and LUMO

Table 1

[0147] It can be seen from Table 1 that the compounds disclosed in the present invention have relatively appropriate HOMO / LUMO, and these compounds are suitable for use as host materials for the light-emitting layer. The bulk material of the light-emitting layer manufactured according to the present invention is applied to an OLED device, and the performance such as the light-emitting efficiency and service life of the device can be effectively improved.

[0148] Next, taking some of the compounds provided by the present invention as examples, they are applied as light-emitting materials to organic electroluminescence devices to verify the excellent effects obtained.

[0149] Comparative Example 1 This comparative example provides an organic electroluminescence device. Its structure is specifically as shown in Figure 1, and includes a substrate 1, an anode layer 2, a hole injection layer 3, a first hole transport layer 4, a second hole transport layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode layer 10, which are sequentially stacked and installed.

[0150] Here, the material of the anode layer 2 is indium tin oxide (ITO) with a high work function, the material of the hole injection layer 3 is HAT-CN, the thickness is 5 nm, the material of the first hole transport layer 4 is HT1, the thickness is 60 nm, the material of the second hole transport layer 5 is HT2, the thickness is 15 nm, the light-emitting layer 6 uses BH1 as the host material of the light-emitting layer and BD01 as the light-emitting material, the doping mass ratio is 5%, the thickness is 30 nm, the material of the hole blocking layer 7 is HB, the thickness is 10 nm, the material of the electron transport layer 8 is ET-1, the thickness is 30 nm, the material of the electron injection layer 9 is Liq, the thickness is 2 nm, and the material of the cathode layer is Al, the thickness is 100 nm.

[0151] The basic material structural formulas used in each functional layer of the device are as follows.

[0152]

Chemical formula

[0153] The specific manufacturing procedure of the above organic electroluminescence device is as follows. 1) Clean the ITO anode on a transparent glass or plastic substrate, perform ultrasonic cleaning for more than 20 minutes each using deionized water, acetone, and ethanol, and then perform plasma treatment in an oxygen atmosphere for 5 minutes. 2) Deposit the hole injection layer material HAT-CN on the ITO anode layer by vacuum evaporation to a thickness of 5 nm, and use this layer as the hole injection layer 3. 3) Deposit the hole transport material HT1 on the hole injection layer 3 by vacuum evaporation to a thickness of 60 nm, and use this layer as the first hole transport layer 4. 4) Deposit the hole transport material HT2 on the first hole transport layer HT1 by vacuum evaporation to a thickness of 15 nm, and use this layer as the second hole transport layer 5. 5) Co-deposit the light-emitting layer 6 on the second hole transport layer 5 by vacuum evaporation, use BH1 as the host material of the light-emitting layer and BD01 as the light-emitting material, the doping mass ratio is 5%, and the thickness is 30 nm. 6) On the light-emitting layer 6, a hole-blocking material HB was deposited by vacuum evaporation to a thickness of 10 nm, and this layer was used as the hole-blocking layer 7. 7) On the hole-blocking layer 7, an electron-transporting material ET-1 was deposited by vacuum evaporation to a thickness of 30 nm, and this layer was used as the electron-transporting layer 8. 8) On the electron-transporting layer 8, an electron-injecting material Liq was deposited by vacuum evaporation to a thickness of 2 nm, and this layer was used as the electron-injecting layer 9. 9) On the electron-injecting layer 9, a cathode Al was deposited by vacuum evaporation to a thickness of 100 nm, and this layer was used as the cathode conductive electrode, which was designated as the cathode layer 10.

[0154] Example 22 This example provides an organic electroluminescence device. The difference from Comparative Example 1 is that compound 3 was used as the host material of the light-emitting layer instead of BH1, which is the host material of the light-emitting layer in Comparative Example 1.

[0155] Example 23 This example provides an organic electroluminescence device. The difference from Comparative Example 1 is that compound 14 was used as the host material of the light-emitting layer instead of BH1, which is the host material of the light-emitting layer in Comparative Example 1.

[0156] Example 24 This example provides an organic electroluminescence device. The difference from Comparative Example 1 is that compound 71 was used as the host material of the light-emitting layer instead of BH1, which is the host material of the light-emitting layer in Comparative Example 1.

[0157] Example 25 This example provides an organic electroluminescence device. The difference from Comparative Example 1 is that compound 72 was used as the host material of the light-emitting layer instead of BH1, which is the host material of the light-emitting layer in Comparative Example 1.

[0158] Example 26 This example provides an organic electroluminescence device. The difference from Comparative Example 1 is that compound 80 was used as the host material of the light-emitting layer instead of BH1, which is the host material of the light-emitting layer in Comparative Example 1.

[0159] Example 27 This example provides an organic electroluminescent device. The difference from Comparative Example 1 is that compound 105 is used as the host material of the light-emitting layer instead of BH1 which is the host material of the light-emitting layer in Comparative Example 1.

[0160] Example 28 This example provides an organic electroluminescent device. The difference from Comparative Example 1 is that compound 131 is used as the host material of the light-emitting layer instead of BH1 which is the host material of the light-emitting layer in Comparative Example 1.

[0161] Example 29 This example provides an organic electroluminescent device. The difference from Comparative Example 1 is that compound 142 is used as the host material of the light-emitting layer instead of BH1 which is the host material of the light-emitting layer in Comparative Example 1.

[0162] Example 30 This example provides an organic electroluminescent device. The difference from Comparative Example 1 is that compound 159 is used as the host material of the light-emitting layer instead of BH1 which is the host material of the light-emitting layer in Comparative Example 1.

[0163] Example 31 This example provides an organic electroluminescent device. The difference from Comparative Example 1 is that compound 160 is used as the host material of the light-emitting layer instead of BH1 which is the host material of the light-emitting layer in Comparative Example 1.

[0164] Example 32 This example provides an organic electroluminescent device. The difference from Comparative Example 1 is that compound 161 is used as the host material of the light-emitting layer instead of BH1 which is the host material of the light-emitting layer in Comparative Example 1.

[0165] Example 33 This example provides an organic electroluminescent device. The difference from Comparative Example 1 is that compound 165 is used as the host material of the light-emitting layer instead of BH1 which is the host material of the light-emitting layer in Comparative Example 1.

[0166] The manufacturing processes of the structures of Examples 22 to 33 and Comparative Example 1 are exactly the same. The same glass substrate and electrode material are used, and the film thickness of the electrode material is also the same. The difference is that the host material of the light-emitting layer is adjusted.

[0167] The constituent components of the different devices manufactured in Examples 22 to 33 and Comparative Example 1 of the present invention are as shown in Table 2.

[0168] Table 2 Comparative table of the constituent components of the organic electroluminescence devices of the examples of each device

Table 2

[0169] For the organic electroluminescence devices manufactured in Examples 22 to 34 and Comparative Example 1, the anode and cathode were connected using a known drive circuit, and the relationship between the voltage - efficiency - current density of the OLED device was tested by a standard method combining a Keithley 2400 power supply and a PR670 photometer. The lifetime of the device was tested by the constant current method, and the test condition was a constant current with a density of 1000 cd / cm 2 The time it takes for the luminance of the test to decay to 70% of the initial luminance is the lifetime of the device LT70, and the test results are as shown in Table 3.

[0170] Table 3 Performance results of the organic electroluminescence devices of each group

Table 3

[0171] As can be seen from Table 3, the compounds provided by the present invention are applied to OLED devices as host materials for the light-emitting layer and exhibit excellent performance. For example, when Compound 80 of Example 26 was used as a blue light host material, compared with BH1 of Comparative Example 1, the luminous efficiency and service life were significantly improved. The luminous efficiency was improved by 43.4%, and the device life was improved by 46.7%. Compared with the comparative material BH1, the deuterated material Compound 165 had a 47.2% increase in the luminous efficiency of the device and a 66.7% increase in the device life. When the compound of the present invention is selected as the host material for the light-emitting layer, compared with the existing materials applied to OLED light-emitting devices, the device has good luminous efficiency and life performance, has great application value in the application to OLED devices, and it can be seen that the industrialization prospect is also good.

[0172] The present invention modifies naphthofluorenes, naphthofuranofluorenes, naphthofuranofurans, naphthothienothiophenes, naphthothienofurans, naphthothienofluorenes, naphthofluorenothiophenes, and the core skeletons of naphthofluorenes and fluorenes by bonding condensed ring groups such as anthracenyl groups, naphthyl groups, pyrenyl groups, phenanthrofuranyl groups, spirofluorenyl groups, and xanthyl groups at fixed substitution positions to obtain condensed ring compounds with new structures, and further performs deuteration based on this. Compounds of this type have appropriate frontier orbital energy levels and higher triplet energy values. It can be seen that the series of compounds obtained exhibit excellent properties as host materials for the light-emitting layer of organic electroluminescence (OLED) devices and have a great effect on improving the efficiency and life of the devices.

[0173] In this way, the present invention can be better realized. The above embodiments illustrate the preferred embodiments of the present invention and do not limit the scope of the present invention. Without departing from the design spirit of the present invention, various changes and improvements made by those skilled in the art to the technical solutions of the present invention shall be included within the protection scope of the present invention.

Explanation of Reference Signs

[0174] 1 Substrate, 2 Anode layer, 3 Hole injection layer, 4 First hole transport layer, 5 Second hole transport layer, 6 Light emitting layer, 7 Hole blocking layer, 8 Electron transport layer, 9 Electron injection layer, 10 Cathode layer

Claims

1. having a chemical structural formula as shown in formula (I), formula (II), or formula (III), 【Chemical Formula 1】 X is an O atom, an S atom, CR １３ R １４ and Y is an O atom, an S atom, CR １５ R １６ wherein R １３ , R １４ , R １５ , R １６ are each independently selected from a methyl group or a phenyl group, L is a single bond, a phenyl group which may be deuterated or non-deuterated, a naphthyl group which may be deuterated or non-deuterated, an anthryl group which may be deuterated or non-deuterated, a pyrenyl group which may be deuterated or non-deuterated, a chrysenyl group which may be deuterated or non-deuterated, a phenanthryl group which may be deuterated or non-deuterated, a benzoxanthenyl group which may be deuterated or non-deuterated, a phenanthrolfuryl group which may be deuterated or non-deuterated, Ar is a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, an aryl group in which a hydrogen atom is partially deuterated and substituted, an aryl group in which a hydrogen atom is completely deuterated and substituted, a heteroaryl group in which a hydrogen atom is partially deuterated and substituted, a heteroaryl group in which a hydrogen atom is completely deuterated and substituted, (Ar) ｎ are n groups selected from Ar, where n is an integer from 0 to 5, R １ to R １２ is a condensed ring compound, characterized in that each of them is independently selected from hydrogen or deuterium.

2. The condensed ring compound according to claim 1, wherein the aryl group is any one of a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, a phenanthryl group, a chrysenyl group, a spirofluorenyl group, a xanthenyl group, a phenanthrolfuryl group.

3. The condensed ring compound according to claim 1, wherein the heteroaryl group is a heteroaryl group containing N, O, or S.

4. The condensed ring compound according to claim 1, wherein the condensed ring compound is one selected from the following structural formulas, where B represents a substituted or unsubstituted phenyl group. 【Chemical 2】

5. The condensed ring compound includes chemical structural formulas shown in Compounds 1 to 190, The condensed ring compound according to claim 1, wherein D indicates that a hydrogen atom is replaced by deuterium. [Chemical Formula 3] 【Chemical Formula 4】 【Chemical Formula 5】 【Chemical Formula 6】 【Chemical Formula 7】 [Chemical Formula 8] 【Chemical Formula 9】 【Chemical Formula 10】 【Chemical 11】 【Chemical Formula 12】 【Chemical 13】 【Chemical 14】

6. The method for preparing the condensed ring compound is to mix an intermediate, Compound (I), potassium carbonate, tetrabutylammonium bromide, toluene, ethanol, and pure water and react them to obtain the condensed ring compound, The intermediate is any one of Intermediate 1, Intermediate 2, Intermediate 3, Intermediate 4, Intermediate 5, Intermediate 6, Intermediate 7, Intermediate 8, and the specific chemical structural formula is as follows. The condensed ring compound according to claim 1. 【Chemical Formula 15】

7. The condensed ring compound according to claim 6, wherein the compound (I) is naphthofuranofluorene, naphthofuranofuran, naphthofluorenofuran, naphthofluorenofluorene, naphthothienofuran, naphthothienofluorene, or naphthothienothiophene.

8. Use of the condensed ring compound according to any one of claims 1 to 7 in an organic electroluminescence device.

9. An organic electroluminescence device having a light-emitting layer, wherein the light-emitting layer contains the condensed ring compound according to any one of claims 1 to 7.

10. Use of the organic electroluminescence device according to claim 9 in an organic electroluminescence display device.

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