Phenanthrene-containing organic electroluminescent material, preparation method and application thereof, and luminescent device

Abstract

The invention relates to a phenanthrene-containing organic electroluminescent material, a preparation method and application thereof and a luminescent device.The phenanthrene-containing organic electroluminescent material provided by the invention takes phenanthrene benzofuran and anthracene as basic structural units, can be used as a main body material of a blue fluorescence luminescent layer, and is relatively high in glass transition temperature and high in quantum efficiency; the compound has good electron transmission capability, good film-forming property and stable property, shows high luminous efficiency and stability in blue light devices, and is an ideal blue fluorescent material.

Description

Technical Field

[0001] The present invention relates to the technical field of organic photoelectric material applications, and in particular to a phenanthrene-containing organic electroluminescent material and a preparation method, application and light-emitting device thereof. Background Art

[0002] With the development of science and technology, the living standards of modern people have changed with each passing day, and the requirements for display technology are also constantly increasing. Among the existing technologies, OLED technology has the advantages of high contrast, flexibility, wide viewing angle, and fast response speed, which makes OLED technology have good potential to replace traditional display technology.

[0003] Existing organic electroluminescent devices generally include a cathode, an electron injection layer, an electron transport layer, an organic light-emitting layer, a hole transport layer, a hole injection layer, an anode and a substrate arranged from top to bottom. In OLED materials, in order to achieve OLED full-color display, blue light materials, as one of the three primary colors, can achieve efficient and stable blue light emission. As a main material, it can obtain green and red light through energy transfer.

[0004] Devices made from existing materials have a short lifespan and low efficiency, and cannot meet the needs of market development. Therefore, how to provide a main material with high efficiency and long lifespan for organic electroluminescent devices has become an urgent problem to be solved. Summary of the invention

[0005] Based on this, in view of the current technical deficiencies, the purpose of the present invention is to provide a phenanthrene-containing organic electroluminescent material and its preparation method, application and light-emitting device. The phenanthrene-containing organic electroluminescent material uses phenanthrenebenzofuran and anthracene as basic structural units, can promote charge transition between molecules, has high photothermal stability, and can achieve rapid electron flow, and is an ideal blue fluorescent material.

[0006] The present invention provides a phenanthrene-containing organic electroluminescent material, the structure of which is shown in the following formula:

[0007]

[0008] Wherein, Ar is selected from aromatic groups having 6 to 18 carbon atoms in the ring.

[0009] As a further improvement of the above scheme of the present invention, Ar is selected from a deuterated aromatic group having 6 to 18 carbon atoms on the ring.

[0010] As a further improvement of the above scheme of the present invention, Ar is selected from a deuterium-free aromatic group having 6 to 18 carbon atoms on the ring.

[0011] As a further improvement of the above scheme of the present invention, Ar is selected from

[0012] As a further improvement of the above scheme of the present invention, it is one of the compounds represented by the following structural formula:

[0013]

[0014]

[0015]

[0016]

[0017] The present invention provides a method for preparing the above-mentioned phenanthrene-containing organic electroluminescent material, and the synthesis route thereof is as follows:

[0018]

[0019] Wherein, Ar is selected from aromatic groups having 6 to 18 carbon atoms in the ring.

[0020] As a further improvement of the above scheme of the present invention, the preparation method of the compound A is as follows: 1-bromo-4-chloro-2-fluorobenzene is subjected to n-butyl lithium extraction of bromine, and then reacted with tri-n-butyl borate to obtain product one; product one is reacted with 2-bromo-3-methoxyphenanthrene and palladium acetate to obtain product two; product two is dissolved in DCM, and BBr3 is added for demethylation to obtain product three; product three is dissolved in NMP, potassium carbonate is added for reaction and cyclization to obtain product four; product four is reacted with bipyralidone to obtain compound A.

[0021] As a further improvement of the above scheme of the present invention, the preparation method of the compound B is: o-fluoronitrobenzene is reacted with p-bromoaniline to obtain product 1; product 1 is reduced with sodium dithionite to obtain product 2; aromatic ethyl ketone is reacted with sodium sulfite to obtain product 3; product 2 is reacted with product 3 to obtain product 4; product 4 is reacted with diboric acid pinacol ester to obtain compound B.

[0022] The present invention provides an application of the above-mentioned phenanthrene-containing organic electroluminescent material in an organic electroluminescent device.

[0023] The present invention provides an organic electroluminescent device, which comprises an organic light-emitting layer. The organic light-emitting layer is made of the above-mentioned phenanthrene-containing organic electroluminescent material.

[0024] Compared with the prior art, the present invention has the following beneficial effects:

[0025] The present invention provides a phenanthrene-containing organic electroluminescent material, which uses phenanthrenebenzofuran and anthracene as basic structural units, can promote charge transition between molecules, has high photothermal stability, and can achieve rapid electron flow. When used as the main material of a blue fluorescent light-emitting layer, it has a high glass transition temperature, high quantum efficiency, good electron transmission ability, good film-forming properties and stable properties. In a blue light device, it exhibits high luminous efficiency and stability, and is an ideal blue fluorescent material.

[0026] The method for preparing the phenanthrene-containing organic electroluminescent material of the present invention has simple specific operation, safe reaction process, and is convenient for expanded production; the present invention applies the above-mentioned organic electroluminescent compound to prepare an organic electroluminescent device, which can increase the service life of the organic electroluminescent device, and exhibits a relatively low driving voltage, excellent luminous efficiency and high-purity color. DETAILED DESCRIPTION

[0027] For ease of understanding of the present invention, the present invention will be described more fully below in conjunction with specific embodiments. However, the present invention can be implemented in many different forms and is not limited to the embodiments described herein. On the contrary, the purpose of providing these embodiments is to make the disclosure of the present invention more thoroughly understood.

[0028] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art of the present invention. The terms used in the specification of the present invention herein are only for the purpose of describing specific embodiments and are not intended to limit the present invention.

[0029] Implementation Case 1

[0030] This embodiment proposes a phenanthrene-containing luminescent material, whose structural formula is

[0031]

[0032] The preparation method of compound 4 comprises the following steps:

[0033] (1) Preparation of compound A:

[0034] Step 1, 1-bromo-4-chloro-2-fluorobenzene (400mmol, 1.0eq) was dissolved in tetrahydrofuran (800ml, 10v / w) and n-butyl lithium (520mmol, 1.3eq) was added to remove bromine, and then reacted with tri-n-butyl borate (600mmol, 1.5eq). After acidification, 59.3g of product I was obtained, with a yield of 85%;

[0035] Step 2: Reflux product I (330 mmol, 1.1 eq) with 2-bromo-3-methoxyphenanthrene (300 mmol, 1.0 eq), palladium acetate (0.005 eq), toluene (600 ml, 7 v / w), ethanol (85 ml, v / w), and water (260 ml, 3 v / w) to obtain 86.9 g of product II after purification, with a yield of 86%;

[0036] Step 3, product II (86.9 g, 258 mmol) was dissolved in DCM (435 ml, 5 V / W), and boron tribromide (335 mmol, 1.3 eq) was added dropwise under ice bath for demethylation, and the mixture was reacted under ice bath for 1 h. After post-treatment, 83.3 g of product III was obtained, with a yield of 100%;

[0037] Step 4, dissolve product III (83.3 g, 258 mmol) in NMP (417 ml, 5 V / W), add potassium carbonate (387 mmol, 1.5 eq) and react at 170-180°C for 1 h, concentrate to remove most of the NMP, add water to precipitate the product, filter and dry to obtain 74.2 g of product IV, with a yield of 95%;

[0038] Step 5: Product IV (74.2 g, 245 mmol, 1.0 eq), biboric acid pinacol ester (319 mmol, 1.3 eq), potassium acetate (490 mmol, 2 eq), Pd 2 (dba) 3 (0.005eq), X-phos (0.01eq) and 1,4-dioxane (600ml, 8v / w) were refluxed for 2h, and then post-processed and purified to obtain 86.9g of compound A with a yield of 90%;

[0039]

[0040] (2) Preparation of compound B:

[0041] Step 1, o-fluoronitrobenzene (400 mmol) and p-bromoaniline (400 mmol) were dissolved in 400 ml of THF, and sodium tert-butoxide (600 mol) was added in batches. After the addition was completed, the mixture was refluxed for 3 h, quenched with water, and recrystallized from toluene to obtain 59.8 g of the product, with a yield of 51%;

[0042] Step 2: Add the product obtained in step 1 (59.8 g, 204 mmol), 300 ml of ethanol, 300 ml of water, and sodium dithionite (306 mmol) into a reaction bottle, reflux for 2 h, filter and wash with water to obtain 53.7 g of the product, with a yield of 100%;

[0043] Step 3, add 400 mmol of acetophenone, 1.2 mol of sodium sulfite, 48 ml of ethanol and 240 ml of water into a reaction bottle, stir at room temperature for 2 h, filter and wash with water to obtain 77.3 g of solid, with a yield of 92%;

[0044] Step 4: Add the product obtained in step 2 (52.4 g, 200 mmol) and the product obtained in step 3 (58.9 g, 280 mmol) into 400 ml of DMF and react at 130°C for 1 h. Pour the reaction solution into water, filter, dry, dissolve in toluene, pass through a column, concentrate and crystallize to obtain 60.8 g, with a yield of 87%;

[0045] Step 5, the product obtained in step 4 (60.8 g, 174 mmol), bipyralidone (209 mmol), potassium acetate (350 mmol), Pd(dppf)Cl2 (0.87 mmol), 1,4-dioxane 500 ml, reflux reaction for 2 h, concentrate to remove most of 1,4-dioxane, add dichloromethane to dissolve, concentrate through a column until a large amount of solid precipitates, add petroleum ether to crystallize, filter and dry to obtain 59.3 g of white solid, which is compound B, with a yield of 86%;

[0046]

[0047] (3) Add 200 mmol of 9-bromoanthracene, 210 mmol of compound A, 400 mmol of potassium carbonate, 2 mmol of palladium acetate, 400 ml of toluene, 50 ml of ethanol, and 150 ml of water to the reaction flask, replace with nitrogen, heat to reflux reaction for 4-8 hours, and stop the reaction after the reaction of 9-bromoanthracene raw material is completed. Cool to room temperature, filter, wash the filter cake with water until neutral, blow dry, pass through a silica gel column after toluene is dissolved, concentrate the column liquid, crystallize and filter, dry, and obtain 72.0 g of yellow-green solid S1, with a yield of 81% (calculated based on 9-bromoanthracene);

[0048] (4) Add 150 mmol of yellow-green solid S1, 160 mmol of NBS, and 670 ml of tetrahydrofuran to a reaction flask, reflux for 2 h, stop the reaction, cool to room temperature, add a small amount of sodium bisulfite aqueous solution to quench, concentrate, crystallize, filter the obtained solid, slurry it with ethanol, and dry it to obtain 78.5 g of off-white solid S2, with a yield of 100% (based on the yellow-green solid S1);

[0049] (5) Add 100 mmol of off-white solid S2, 110 mmol of compound B, 200 mmol of potassium carbonate, 0.5 mmol of palladium acetate, 400 ml of toluene, 50 ml of ethanol, and 150 ml of water to the reaction flask, replace with nitrogen, reflux for 2-4 hours, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, slurry the obtained solid with ethanol, filter and dry, dissolve with toluene, pass through a column, concentrate, crystallize, filter and dry to obtain 36.4 g of yellow-green compound 4, with a yield of 51% (based on the off-white solid S2).

[0050] The reaction process is:

[0051]

[0052] Implementation Case 2

[0053] This embodiment proposes a phenanthrene-containing luminescent material, whose structural formula is

[0054]

[0055] The preparation method of compound 7 comprises the following steps:

[0056] (1) Preparation of compound A:

[0057] Step 1, 1-bromo-5-chloro-2-fluorobenzene (400mmol, 1.0eq) was dissolved in tetrahydrofuran (800ml, 10v / w) and n-butyl lithium (520mmol, 1.3eq) was added to remove bromine, and then reacted with tri-n-butyl borate (600mmol, 1.5eq). After acidification, 60g of product I was obtained, with a yield of 86%;

[0058] Step 2: Reflux product I (330 mmol, 1.1 eq) with 2-bromo-3-methoxyphenanthrene (300 mmol, 1.0 eq), palladium acetate (0.005 eq), toluene (600 ml, 7 v / w), ethanol (85 ml, v / w), and water (260 ml, 3 v / w) to obtain 83.9 g of product II after purification, with a yield of 83%;

[0059] Step 3, product II (83.9 g, 249 mmol) was dissolved in DCM (420 ml, 5 V / W), and boron tribromide (324 mmol, 1.3 eq) was added dropwise under ice bath for demethylation, and the mixture was reacted under ice bath for 1 h. After post-treatment, 80.4 g of product III was obtained, with a yield of 100%;

[0060] Step 4, dissolve product III (80.4 g, 249 mmol) in NMP (400 ml, 5 V / W), add potassium carbonate (374 mmol, 1.5 eq) and react at 170-180 ° C for 1 h, concentrate to remove most of the NMP, add water to precipitate the product, filter and dry to obtain 72.4 g of product IV, with a yield of 96%;

[0061] Step 5: Product IV (72.4 g, 239 mmol, 1.0 eq), biboric acid pinacol ester (311 mmol, 1.3 eq), potassium acetate (478 mmol, 2 eq), Pd 2 (dba) 3 (0.005eq), X-phos (0.01eq) and 1,4-dioxane (580ml, 8v / w) were refluxed for 2h, and then post-processed and purified to obtain 83.8g of compound A with a yield of 89%;

[0062]

[0063] (2) Preparation of compound B:

[0064] Step 1, o-fluoronitrobenzene (400 mmol) and p-bromoaniline (400 mmol) were dissolved in 400 ml of THF, and sodium tert-butoxide (600 mol) was added in batches. After the addition was completed, the mixture was refluxed for 3 h, quenched with water, and recrystallized from toluene to obtain 59.8 g of the product, with a yield of 51%;

[0065] Step 2: Add the obtained product (59.8 g, 204 mmol), 300 ml of ethanol, 300 ml of water, and sodium dithionite (306 mmol) into a reaction bottle, reflux for 2 h, filter and wash with water to obtain 53.7 g of the product, with a yield of 100%;

[0066] Step 3, add 400mmol of acetophenone, 1.2mol of sodium sulfite, 48ml of ethanol and 240ml of water into a reaction bottle, stir at room temperature for 2h, filter and wash with water to obtain 77.3g of solid, with a yield of 92%;

[0067] Step 4: The product obtained in step 2 (52.4 g, 200 mmol) and the product obtained in step 3 (58.9 g, 280 mmol) were added to 400 ml of DMF and reacted at 130°C for 1 h. The reaction solution was poured into water, filtered, dried, dissolved in toluene, and concentrated by column to obtain 60.8 g, with a yield of 87%.

[0068] Step 5: The product obtained in step 4 (60.8 g, 174 mmol), bipyralidone (209 mmol), potassium acetate (350 mmol), Pd(dppf)Cl2 (0.87 mmol), and 500 ml of 1,4-dioxane were refluxed for 2 h, and most of the 1,4-dioxane was removed by concentration. Dichloromethane was added to dissolve the mixture and concentrated to a large amount of solid precipitated. Petroleum ether was added for crystallization, and the mixture was filtered and dried to obtain 59.3 g of a white solid, which was compound B, with a yield of 86%.

[0069]

[0070] (3) Add 200 mmol of 9-bromoanthracene, 210 mmol of compound A, 400 mmol of potassium carbonate, 2 mmol of palladium acetate, 400 ml of toluene, 50 ml of ethanol, and 150 ml of water to the reaction flask, replace with nitrogen, heat to reflux reaction for 4-8 hours, and stop the reaction after the reaction of 9-bromoanthracene raw material is completed. Cool to room temperature, filter, wash the filter cake with water until neutral, blow dry, pass through a silica gel column after toluene is dissolved, concentrate the column liquid, crystallize and filter, dry, and obtain 72.0 g of yellow-green solid S1, with a yield of 81% (calculated based on 9-bromoanthracene);

[0071] (4) Add 150 mmol of yellow-green solid S1, 160 mmol of NBS, and 670 ml of tetrahydrofuran to the reaction flask, reflux for 2 h, stop the reaction, cool to room temperature, add a small amount of sodium bisulfite aqueous solution to quench, concentrate, crystallize, filter the obtained solid, slurry it with ethanol, and dry it to obtain 78.5 g of off-white solid S2, with a yield of 100% (based on the yellow-green solid S1);

[0072] (5) Add 100 mmol of off-white solid S2, 110 mmol of compound B, 200 mmol of potassium carbonate, 0.5 mmol of palladium acetate, 400 ml of toluene, 50 ml of ethanol, and 150 ml of water to the reaction flask, replace with nitrogen, reflux for 2-4 hours, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, slurry the obtained solid with ethanol, filter and dry, dissolve with toluene, pass through a column, concentrate, crystallize, filter and dry to obtain 36.4 g of yellow-green compound 4, with a yield of 51% (based on the off-white solid S2).

[0073] The reaction process is:

[0074]

[0075] Implementation Case 3

[0076] This embodiment proposes a phenanthrene-containing luminescent material, whose structural formula is

[0077]

[0078] The preparation method of compound 10 comprises the following steps:

[0079] (1) Preparation of compound A:

[0080] Step 1, 1-bromo-6-chloro-2-fluorobenzene (400mmol, 1.0eq) was dissolved in tetrahydrofuran (800ml, 10v / w) and n-butyl lithium (520mmol, 1.3eq) was added to remove bromine, and then reacted with tri-n-butyl borate (600mmol, 1.5eq). After acidification, 60.7g of product I was obtained, with a yield of 87%;

[0081] Step 2: Reflux product I (330 mmol, 1.1 eq) with 2-bromo-3-methoxyphenanthrene (300 mmol, 1.0 eq), palladium acetate (0.005 eq), toluene (600 ml, 7 v / w), ethanol (85 ml, v / w), and water (260 ml, 3 v / w) to obtain 75.8 g of product II after purification, with a yield of 75%;

[0082] Step 3, dissolve product II (75.8 g, 225 mmol) in DCM (435 ml, 5 V / W), add boron tribromide (335 mmol, 1.3 eq) dropwise under ice bath for demethylation, react under ice bath for 1 h, and post-treat to obtain 72.6 g of product III, with a yield of 100%;

[0083] Step 4, dissolve product III (72.6 g, 225 mmol) in NMP (360 ml, 5 V / W), add potassium carbonate (338 mmol, 1.5 eq) and react at 170-180 ° C for 1 h, concentrate to remove most of the NMP, add water to precipitate the product, filter and dry to obtain 65.4 g of product IV, with a yield of 96%;

[0084] Step 5: Product IV (65.4 g, 216 mmol, 1.0 eq), biboric acid pinacol ester (281 mmol, 1.3 eq), potassium acetate (432 mmol, 2 eq), Pd 2 (dba) 3 (0.005eq), X-phos (0.01eq) and 1,4-dioxane (525ml, 8v / w) were refluxed for 2h, and then purified to obtain 76.6g of compound A with a yield of 90%;

[0085]

[0086] (2) Preparation of compound B:

[0087] Step 1, o-fluoronitrobenzene (400 mmol) and p-bromoaniline (400 mmol) were dissolved in 400 ml of THF, and sodium tert-butoxide (600 mol) was added in batches. After the addition was completed, the mixture was refluxed for 3 h, quenched with water, and recrystallized from toluene to obtain 59.8 g of the product, with a yield of 51%;

[0088] Step 2: Add the product obtained in step 1 (59.8 g, 204 mmol), 300 ml of ethanol, 300 ml of water, and sodium dithionite (306 mmol) into a reaction flask, reflux for 2 h, filter and wash with water to obtain 53.7 g of the product, with a yield of 100%;

[0089] Step 3, add 400mmol of acetophenone, 1.2mol of sodium sulfite, 48ml of ethanol and 240ml of water into a reaction bottle, stir at room temperature for 2h, filter and wash with water to obtain 77.3g of solid, with a yield of 92%;

[0090] Step 4: Add the product obtained in step 2 (52.4 g, 200 mmol) and the product obtained in step 3 (58.9 g, 280 mmol) into 400 ml of DMF and react at 130°C for 1 h. Pour the reaction solution into water, filter, dry, dissolve in toluene, pass through a column, concentrate and crystallize to obtain 60.8 g, with a yield of 87%;

[0091] Step 5: The product obtained in step 4 (60.8 g, 174 mmol), bipyralidone (209 mmol), potassium acetate (350 mmol), Pd(dppf)Cl2 (0.87 mmol), and 500 ml of 1,4-dioxane were refluxed for 2 h, and most of the 1,4-dioxane was removed by concentration. Dichloromethane was added to dissolve the mixture and concentrated to a large amount of solid precipitated. Petroleum ether was added for crystallization, and the mixture was filtered and dried to obtain 59.3 g of a white solid, which was compound B, with a yield of 86%.

[0092]

[0093] (3) Add 200 mmol of 9-bromoanthracene, 210 mmol of compound A, 400 mmol of potassium carbonate, 2 mmol of palladium acetate, 400 ml of toluene, 50 ml of ethanol, and 150 ml of water to the reaction flask, replace with nitrogen, heat to reflux reaction for 4-8 hours, and stop the reaction after the reaction of 9-bromoanthracene raw material is completed. Cool to room temperature, filter, wash the filter cake with water until neutral, blow dry, pass through a silica gel column after toluene is dissolved, concentrate the column liquid, crystallize and filter, dry, and obtain 72.0 g of yellow-green solid S1, with a yield of 81% (calculated based on 9-bromoanthracene);

[0094] (4) Add 150 mmol of yellow-green solid S1, 160 mmol of NBS, and 670 ml of tetrahydrofuran to the reaction flask, reflux for 2 h, stop the reaction, cool to room temperature, add a small amount of sodium bisulfite aqueous solution to quench, concentrate, crystallize, filter the obtained solid, slurry it with ethanol, and dry it to obtain 78.5 g of off-white solid S2, with a yield of 100% (based on the yellow-green solid S1);

[0095] (5) Add 100 mmol of off-white solid S2, 110 mmol of compound B, 200 mmol of potassium carbonate, 0.5 mmol of palladium acetate, 400 ml of toluene, 50 ml of ethanol, and 150 ml of water to the reaction flask, replace with nitrogen, reflux for 2-4 hours, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, slurry the obtained solid with ethanol, filter and dry, dissolve with toluene, pass through a column, concentrate, crystallize, filter and dry to obtain 36.4 g of yellow-green compound 4, with a yield of 51% (based on the off-white solid S2).

[0096] The reaction process is:

[0097]

[0098] Implementation Case 4

[0099] This embodiment proposes a phenanthrene-containing luminescent material, whose structural formula is

[0100]

[0101] The preparation method of compound 14 comprises the following steps:

[0102] (1) Preparation of compound A:

[0103] Step 1, 1-bromo-4-chloro-2-fluorobenzene (400mmol, 1.0eq) was dissolved in tetrahydrofuran (800ml, 10v / w) and n-butyl lithium (520mmol, 1.3eq) was added to remove bromine, and then reacted with tri-n-butyl borate (600mmol, 1.5eq). After acidification, 59.3g of product I was obtained, with a yield of 85%;

[0104] Step 2: Reflux product I (330 mmol, 1.1 eq) with 2-bromo-3-methoxyphenanthrene (300 mmol, 1.0 eq), palladium acetate (0.005 eq), toluene (600 ml, 7 v / w), ethanol (85 ml, v / w), and water (260 ml, 3 v / w) to obtain 86.9 g of the product after purification, with a yield of 86%;

[0105] Step 3, product II (86.9 g, 258 mmol) was dissolved in DCM (435 ml, 5 V / W), and boron tribromide (335 mmol, 1.3 eq) was added dropwise under ice bath for demethylation, and the mixture was reacted under ice bath for 1 h. After post-treatment, 83.3 g of product III was obtained, with a yield of 100%;

[0106] Step 4, dissolve product III (83.3 g, 258 mmol) in NMP (417 ml, 5 V / W), add potassium carbonate (387 mmol, 1.5 eq) and react at 170-180°C for 1 h, concentrate to remove most of the NMP, add water to precipitate the product, filter and dry to obtain 74.2 g of product IV, with a yield of 95%;

[0107] Step 5: Product IV (74.2 g, 245 mmol, 1.0 eq), pinacol diboron (319 mmol, 1.3 eq), potassium acetate (490 mmol, 2 eq), Pd 2 (dba) 3 (0.005eq), X-phos (0.01eq) and 1,4-dioxane (600ml, 8v / w) were refluxed for 2h, and then purified to obtain 86.9g of compound A with a yield of 90%;

[0108]

[0109] (2) Preparation of compound B:

[0110] Step 1, o-fluoronitrobenzene (400 mmol) and p-bromoaniline (400 mmol) were dissolved in 400 ml of THF, and sodium tert-butoxide (600 mol) was added in batches. After the addition was completed, the mixture was refluxed for 3 h, quenched with water, and recrystallized from toluene to obtain 59.8 g of the product, with a yield of 51%;

[0111] Step 2: Add the product obtained in step 1 (59.8 g, 204 mmol), 300 ml of ethanol, 300 ml of water, and sodium dithionite (306 mmol) into a reaction flask, reflux for 2 h, filter and wash with water to obtain 53.7 g of the product, with a yield of 100%;

[0112] Step 3, add 400 mmol of deuterated acetophenone, 1.2 mol of sodium sulfite, 50 ml of ethanol and 250 ml of water into a reaction bottle, stir at room temperature for 2 h, filter and wash with water to obtain 80 g of solid, with a yield of 93%;

[0113] Step 4: Add the product obtained in step 2 (52.4 g, 200 mmol) and the product obtained in step 3 (60.3 g, 280 mmol) into 400 ml of DMF and react at 130°C for 1 h. Pour the reaction solution into water, filter, dry, dissolve in toluene, pass through a column, concentrate and crystallize to obtain 60.2 g of the product, with a yield of 85%;

[0114] Step 5, the product obtained in step 4 (60.2 g, 170 mmol), biboronic acid pinacol ester (204 mmol), potassium acetate (340 mmol), Pd (dppf) Cl2 (0.85 mmol), 1,4-dioxane 480 ml were added to a reaction bottle, refluxed for 2 h, concentrated to remove most of the 1,4-dioxane, added dichloromethane to dissolve, concentrated to a column until a large amount of solid precipitated, added petroleum ether to crystallize, filtered and dried to obtain 59.4 g of white solid, which is compound B, with a yield of 87%;

[0115]

[0116] (3) Add 200 mmol of 9-bromoanthracene, 210 mmol of compound A, 400 mmol of potassium carbonate, 2 mmol of palladium acetate, 400 ml of toluene, 50 ml of ethanol, and 150 ml of water to the reaction flask, replace with nitrogen, heat to reflux reaction for 4-8 hours, and stop the reaction after the reaction of 9-bromoanthracene raw material is completed. Cool to room temperature, filter, wash the filter cake with water until neutral, blow dry, pass through a silica gel column after toluene is dissolved, concentrate the column liquid, crystallize and filter, dry, and obtain 72.0 g of yellow-green solid S1, with a yield of 81% (calculated based on 9-bromoanthracene);

[0117] (4) Add 150 mmol of yellow-green solid S1, 160 mmol of NBS, and 670 ml of tetrahydrofuran to the reaction flask, reflux for 2 h, stop the reaction, cool to room temperature, add a small amount of sodium bisulfite aqueous solution to quench, concentrate, crystallize, filter the obtained solid, slurry it with ethanol, and dry it to obtain 78.5 g of off-white solid S2, with a yield of 100% (based on the yellow-green solid S1);

[0118] (5) Add 100 mmol of off-white solid S2, 110 mmol of compound B, 200 mmol of potassium carbonate, 0.5 mmol of palladium acetate, 400 ml of toluene, 50 ml of ethanol, and 150 ml of water to the reaction flask, replace with nitrogen, reflux for 2-4 hours, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, slurry the obtained solid with ethanol, filter and dry, dissolve with toluene, pass through a column, concentrate, crystallize, filter and dry to obtain 36.4 g of yellow-green compound 4, with a yield of 51% (based on the off-white solid S2).

[0119] The reaction process is:

[0120]

[0121] Compound 14 was tested by LCMS, and the data obtained were as follows: ESI-MS: C 53 H 27 D 5 N 2 O, standard molecular weight 717.86, test result 7172.35 [M+].

[0122] Implementation Case 5

[0123] This embodiment proposes a phenanthrene-containing luminescent material, whose structural formula is

[0124]

[0125] The preparation method of compound 18 comprises the following steps:

[0126] (1) Preparation of compound A:

[0127] Step 1, 1-bromo-4-chloro-2-fluorobenzene (400mmol, 1.0eq) was dissolved in tetrahydrofuran (800ml, 10v / w) and n-butyl lithium (520mmol, 1.3eq) was added to remove bromine, and then reacted with tri-n-butyl borate (600mmol, 1.5eq). After acidification, 59.3g of product I was obtained, with a yield of 85%;

[0128] Step 2: Reflux product I (330 mmol, 1.1 eq), 2-bromo-3-methoxyphenanthrene (300 mmol, 1.0 eq) with palladium acetate (0.005 eq), toluene (600 ml, 7 v / w), ethanol (85 ml, v / w), and water (260 ml, 3 v / w) to obtain 86.9 g of product II after purification, with a yield of 86%;

[0129] Step 3, product II (86.9 g, 258 mmol) was dissolved in DCM (435 ml, 5 V / W), and boron tribromide (335 mmol, 1.3 eq) was added dropwise under ice bath for demethylation, and the mixture was reacted under ice bath for 1 h. After post-treatment, 83.3 g of product III was obtained, with a yield of 100%;

[0130] Step 4, dissolve product III (83.3 g, 258 mmol) in NMP (417 ml, 5 V / W), add potassium carbonate (387 mmol, 1.5 eq) and react at 170-180°C for 1 h, concentrate to remove most of the NMP, add water to precipitate the product, filter and dry to obtain 74.2 g of product IV, with a yield of 95%;

[0131] Step 5: Product IV (74.2 g, 245 mmol, 1.0 eq), biboric acid pinacol ester (319 mmol, 1.3 eq), potassium acetate (490 mmol, 2 eq), Pd 2 (dba) 3 (0.005eq), X-phos (0.01eq) and 1,4-dioxane (600ml, 8v / w) were refluxed for 2h, and then purified to obtain 86.9g of compound A with a yield of 90%;

[0132]

[0133] (2) Preparation of compound B:

[0134] Step 1, o-fluoronitrobenzene (400 mmol) and p-bromoaniline (400 mmol) were dissolved in 400 ml of THF, and sodium tert-butoxide (600 mol) was added in batches. After the addition was completed, the mixture was refluxed for 3 h, quenched with water, and recrystallized from toluene to obtain 59.8 g of the product, with a yield of 51%;

[0135] Step 2: Add the obtained product (59.8 g, 204 mmol), 300 ml of ethanol, 300 ml of water, and sodium dithionite (306 mmol) into a reaction bottle, reflux for 2 h, filter and wash with water to obtain 53.7 g of the product, with a yield of 100%;

[0136] Step 3, add 400mmol of 1-pyridine-3-ethanone, 1.2mol of sodium sulfite, 50ml of ethanol and 250ml of water into a reaction bottle, stir at room temperature for 2h, filter and wash with water to obtain 75.2g of solid, with a yield of 89%;

[0137] Step 4: Add the product obtained in step 2 (52.4 g, 200 mmol) and the product obtained in step 3 (59.1 g, 280 mmol) into 400 ml of DMF and react at 130°C for 1 h. Pour the reaction solution into water, filter, dry, dissolve in toluene, pass through a column, concentrate and crystallize to obtain 52.5 g of the product, with a yield of 75%;

[0138] Step 5, the product obtained in step 4 (52.5 g, 150 mmol), biboronic acid pinacol ester (180 mmol), potassium acetate (300 mmol), Pd (dppf) Cl2 (0.75 mmol), 1,4-dioxane 420 ml were added to a reaction bottle, refluxed for 2 h, concentrated to remove most of the 1,4-dioxane, added dichloromethane to dissolve, concentrated to a column until a large amount of solid precipitated, added petroleum ether for crystallization, filtered and dried to obtain 51.8 g of white solid, which is compound B, with a yield of 87%;

[0139]

[0140] (3) Add 200 mmol of 9-bromoanthracene, 210 mmol of compound A, 400 mmol of potassium carbonate, 2 mmol of palladium acetate, 400 ml of toluene, 50 ml of ethanol, and 150 ml of water to the reaction flask, replace with nitrogen, heat to reflux reaction for 4-8 hours, and stop the reaction after the reaction of 9-bromoanthracene raw material is completed. Cool to room temperature, filter, wash the filter cake with water until neutral, blow dry, pass through a silica gel column after toluene is dissolved, concentrate the column liquid, crystallize and filter, dry, and obtain 72.0 g of yellow-green solid S1, with a yield of 81% (calculated based on 9-bromoanthracene);

[0141] (4) Add 150 mmol of yellow-green solid S1, 160 mmol of NBS, and 670 ml of tetrahydrofuran to a reaction flask, reflux for 2 h, stop the reaction, cool to room temperature, add a small amount of sodium bisulfite aqueous solution to quench, concentrate, crystallize, filter the obtained solid, slurry it with ethanol, and dry it to obtain 78.5 g of off-white solid S2, with a yield of 100% (based on the yellow-green solid S1);

[0142] (5) Add 100 mmol of off-white solid S2, 110 mmol of compound B, 200 mmol of potassium carbonate, 0.5 mmol of palladium acetate, 400 ml of toluene, 50 ml of ethanol, and 150 ml of water to the reaction flask, replace with nitrogen, reflux for 2-4 hours, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, slurry the obtained solid with ethanol, filter and dry, dissolve with toluene, pass through a column, concentrate, crystallize, filter and dry to obtain 36.4 g of yellow-green compound 4, with a yield of 51% (based on the off-white solid S2).

[0143] The reaction process is:

[0144]

[0145] Compound 18 was tested by LCMS, and the data obtained were as follows: ESI-MS: C 52 H 31 N 3 O, standard molecular weight 713.82, test result 713.32 [M+].

[0146] Implementation Case 6

[0147] This embodiment proposes a phenanthrene-containing luminescent material, whose structural formula is

[0148]

[0149] The preparation method of compound 22 comprises the following steps:

[0150] (1) Preparation of compound A:

[0151] Step 1, 1-bromo-4-chloro-2-fluorobenzene (400mmol, 1.0eq) was dissolved in tetrahydrofuran (800ml, 10v / w) and n-butyl lithium (520mmol, 1.3eq) was added to remove bromine, and then reacted with tri-n-butyl borate (600mmol, 1.5eq). After acidification, 59.3g of product I was obtained, with a yield of 85%;

[0152] Step 2, product I (330mmol, 1.1eq), 2-bromo-3-methoxyphenanthrene (300mmol, 1.0eq) and palladium acetate (0.005eq), toluene (600ml, 7v / w), ethanol (85ml, v / w), water (260ml, 3v / w) were refluxed to obtain 86.9g of product II after purification, with a yield of 86%;

[0153] Step 3, product II (86.9 g, 258 mmol) was dissolved in DCM (435 ml, 5 V / W), and boron tribromide (335 mmol, 1.3 eq) was added dropwise under ice bath for demethylation, and the mixture was reacted under ice bath for 1 h. After post-treatment, 83.3 g of product III was obtained, with a yield of 100%;

[0154] Step 4, dissolve product III (83.3 g, 258 mmol) in NMP (417 ml, 5 V / W), add potassium carbonate (387 mmol, 1.5 eq) and react at 170-180°C for 1 h, concentrate to remove most of the NMP, add water to precipitate the product, filter and dry to obtain 74.2 g of product IV, with a yield of 95%;

[0155] Step 5: Product IV (74.2 g, 245 mmol, 1.0 eq), biboric acid pinacol ester (319 mmol, 1.3 eq), potassium acetate (490 mmol, 2 eq), Pd 2 (dba) 3 (0.005eq), X-phos (0.01eq) and 1,4-dioxane (600ml, 8v / w) were refluxed for 2h, and then purified to obtain 86.9g of compound A with a yield of 90%;

[0156]

[0157] (2) Preparation of compound B:

[0158] Step 1, o-fluoronitrobenzene (400 mmol) and p-bromoaniline (400 mmol) were dissolved in 400 ml of THF, and sodium tert-butoxide (600 mol) was added in batches. After the addition was completed, the mixture was refluxed for 3 h, quenched with water, and recrystallized from toluene to obtain 59.8 g of the product, with a yield of 51%;

[0159] Step 2: Add the obtained product (59.8 g, 204 mmol), 300 ml of ethanol, 300 ml of water, and sodium dithionite (306 mmol) into a reaction bottle, reflux for 2 h, filter and wash with water to obtain 53.7 g of the product, with a yield of 100%;

[0160] Step 3, add 400mmol of 1-naphthalene-2-ethanone, 1.2mol of sodium sulfite, 70ml of ethanol and 350ml of water into a reaction bottle, stir at room temperature for 2h, filter and wash with water to obtain 96.8g of solid, with a yield of 93%;

[0161] Step 4: Add the product obtained in step 2 (52.4 g, 200 mmol) and the product obtained in step 3 (72.9 g, 280 mmol) into 400 ml of DMF and react at 130°C for 1 h. Pour the reaction solution into water, filter, dry, dissolve in toluene, pass through a column, concentrate and crystallize to obtain 67.1 g of the product, with a yield of 84%;

[0162] Step 5, the product obtained in step 4 (67.1 g, 172 mmol), bipyralidone (207 mmol), potassium acetate (344 mmol), Pd(dppf)Cl2 (0.86 mmol), 1,4-dioxane 540 ml were added to a reaction bottle, refluxed for 2 h, concentrated to remove most of the 1,4-dioxane, dissolved in dichloromethane, concentrated to a column until a large amount of solid precipitated, added petroleum ether for crystallization, filtered and dried to obtain 68.3 g of white solid, which is compound B, with a yield of 89%;

[0163]

[0164] (3) Add 200 mmol of 9-bromoanthracene, 210 mmol of compound A, 400 mmol of potassium carbonate, 2 mmol of palladium acetate, 400 ml of toluene, 50 ml of ethanol, and 150 ml of water to the reaction flask, replace with nitrogen, heat to reflux reaction for 4-8 hours, and stop the reaction after the reaction of 9-bromoanthracene raw material is completed. Cool to room temperature, filter, wash the filter cake with water until neutral, blow dry, pass through a silica gel column after toluene is dissolved, concentrate the column liquid, crystallize and filter, dry, and obtain 72.0 g of yellow-green solid S1, with a yield of 81% (calculated based on 9-bromoanthracene);

[0165] (4) Add 150 mmol of yellow-green solid S1, 160 mmol of NBS, and 670 ml of tetrahydrofuran to a reaction flask, reflux for 2 h, stop the reaction, cool to room temperature, add a small amount of sodium bisulfite aqueous solution to quench, concentrate, crystallize, filter the obtained solid, slurry it with ethanol, and dry it to obtain 78.5 g of off-white solid S2, with a yield of 100% (based on the yellow-green solid S1);

[0166] (5) Add 100 mmol of off-white solid S2, 110 mmol of compound B, 200 mmol of potassium carbonate, 0.5 mmol of palladium acetate, 400 ml of toluene, 50 ml of ethanol, and 150 ml of water to the reaction flask, replace with nitrogen, reflux for 2-4 hours, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, slurry the obtained solid with ethanol, filter and dry, dissolve with toluene, pass through a column, concentrate, crystallize, filter and dry to obtain 36.4 g of yellow-green compound 4, with a yield of 51% (based on the off-white solid S2).

[0167] The reaction process is:

[0168]

[0169] Compound 22 was tested by LCMS, and the data obtained were as follows: ESI-MS: C 57 H 34 N 2 O, standard molecular weight 762.89, test result 762.29 [M+].

[0170] Implementation Case 7

[0171] This embodiment proposes a phenanthrene-containing luminescent material, whose structural formula is

[0172]

[0173] The preparation method of compound 34 comprises the following steps:

[0174] (1) Preparation of compound A:

[0175] Step 1, 1-bromo-4-chloro-2-fluorobenzene (400mmol, 1.0eq) was dissolved in tetrahydrofuran (800ml, 10v / w) and n-butyl lithium (520mmol, 1.3eq) was added to remove bromine, and then reacted with tri-n-butyl borate (600mmol, 1.5eq). After acidification, 59.3g of product I was obtained, with a yield of 85%;

[0176] Step 2: Reflux product I (330 mmol, 1.1 eq), 2-bromo-3-methoxyphenanthrene (300 mmol, 1.0 eq) with palladium acetate (0.005 eq), toluene (600 ml, 7 v / w), ethanol (85 ml, v / w), and water (260 ml, 3 v / w) to obtain 86.9 g of product II after purification, with a yield of 86%;

[0177] Step 3, product II (86.9 g, 258 mmol) was dissolved in DCM (435 ml, 5 V / W), and boron tribromide (335 mmol, 1.3 eq) was added dropwise under ice bath for demethylation, and the mixture was reacted under ice bath for 1 h. After post-treatment, 83.3 g of product III was obtained, with a yield of 100%;

[0178] Step 4, dissolve product III (83.3 g, 258 mmol) in NMP (417 ml, 5 V / W), add potassium carbonate (387 mmol, 1.5 eq) and react at 170-180°C for 1 h, concentrate to remove most of the NMP, add water to precipitate the product, filter and dry to obtain 74.2 g of product IV, with a yield of 95%;

[0179] Step 5: Product IV (74.2 g, 245 mmol, 1.0 eq), biboric acid pinacol ester (319 mmol, 1.3 eq), potassium acetate (490 mmol, 2 eq), Pd 2 (dba) 3 (0.005eq), X-phos (0.01eq) and 1,4-dioxane (600ml, 8v / w) were refluxed for 2h, and then purified to obtain 86.9g of compound A with a yield of 90%;

[0180]

[0181] (2) Preparation of compound B:

[0182] Step 1, o-fluoronitrobenzene (400 mmol) and p-bromoaniline (400 mmol) were dissolved in 400 ml of THF, and sodium tert-butoxide (600 mol) was added in batches. After the addition was completed, the mixture was refluxed for 3 h, quenched with water, and recrystallized from toluene to obtain 59.8 g of the product, with a yield of 51%;

[0183] Step 2: Add the product obtained in step 1 (59.8 g, 204 mmol), 300 ml of ethanol, 300 ml of water, and sodium dithionite (306 mmol) into a reaction flask, reflux for 2 h, filter and wash with water to obtain 53.7 g of the product, with a yield of 100%;

[0184] Step 3, add 400mmol of 1-biphenyl-4-ethanone, 1.2mol of sodium sulfite, 80ml of ethanol and 400ml of water into a reaction bottle, stir at room temperature for 2h, filter and wash with water to obtain 104.2g of solid, with a yield of 91%;

[0185] Step 4: Add the product obtained in step 2 (52.4 g, 200 mmol) and the product obtained in step 3 (80.2 g, 280 mmol) into 400 ml of DMF and react at 130°C for 1 h. Pour the reaction solution into water, filter, dry, dissolve in toluene, pass through a column, concentrate and crystallize to obtain 72.3 g of the product, with a yield of 85%;

[0186] Step 5, add the product obtained in step 4 (72.3 g, 170 mmol), bipyralidin (204 mmol), potassium acetate (340 mmol), Pd(dppf)Cl2 (0.85 mmol), and 580 ml of 1,4-dioxane into a reaction flask, reflux for 2 h, concentrate to remove most of the 1,4-dioxane, add dichloromethane to dissolve, concentrate through a column until a large amount of solid precipitates, add petroleum ether for crystallization, filter and dry to obtain 70.7 g of white solid, which is compound B, with a yield of 88%;

[0187]

[0188] (3) Add 200 mmol of 9-bromoanthracene, 210 mmol of compound A, 400 mmol of potassium carbonate, 2 mmol of palladium acetate, 400 ml of toluene, 50 ml of ethanol, and 150 ml of water to the reaction flask, replace with nitrogen, heat to reflux reaction for 4-8 hours, and stop the reaction after the reaction of 9-bromoanthracene raw material is completed. Cool to room temperature, filter, wash the filter cake with water until neutral, blow dry, pass through a silica gel column after toluene is dissolved, concentrate the column liquid, crystallize and filter, dry, and obtain 72.0 g of yellow-green solid S1, with a yield of 81% (calculated based on 9-bromoanthracene);

[0189] (4) Add 150 mmol of yellow-green solid S1, 160 mmol of NBS, and 670 ml of tetrahydrofuran to a reaction flask, reflux for 2 h, stop the reaction, cool to room temperature, add a small amount of sodium bisulfite aqueous solution to quench, concentrate, crystallize, filter the obtained solid, slurry it with ethanol, and dry it to obtain 78.5 g of off-white solid S2, with a yield of 100% (based on the yellow-green solid S1);

[0190] (5) Add 100 mmol of off-white solid S2, 110 mmol of compound B, 200 mmol of potassium carbonate, 0.5 mmol of palladium acetate, 400 ml of toluene, 50 ml of ethanol, and 150 ml of water to the reaction flask, replace with nitrogen, reflux for 2-4 hours, stop the reaction, cool the reactant to room temperature, add water, filter, wash with water, slurry the obtained solid with ethanol, filter and dry, dissolve with toluene, pass through a column, concentrate, crystallize, filter and dry to obtain 36.4 g of yellow-green compound 4, with a yield of 51% (based on the off-white solid S2).

[0191] The reaction process is:

[0192]

[0193] Compound 34 was tested by LCMS, and the data obtained were as follows: ESI-MS: C 59 H 36 N 2 O, standard molecular weight 788.93, test result 788.28 [M+].

[0194] Comparative Case 1

[0195] This comparative case proposes a luminescent material, whose structural formula is

[0196]

[0197] Comparative Case 2

[0198] This comparative case proposes a luminescent material, whose structural formula is

[0199]

[0200] Test Cases

[0201] An OLED device is prepared using the light-emitting materials prepared in the above Examples 1-8 and Comparative Examples 1-2. The OLED device includes a first hole injection layer (HIL-1), a second hole injection layer (HIL-2), a first hole transport layer (HTL-1), a second hole transport layer (HTL-2), an organic light-emitting layer, an electron transport layer (ETL), an electron transport layer, an electron injection layer (EIL) and a cathode (Cthd) sequentially deposited on an ITO substrate.

[0202] The ITO substrate production process is as follows: the glass substrate coated with the ITO transparent conductive layer (as the anode) is ultrasonically treated in a cleaning agent, then rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone and ethanol, and then baked in a clean environment until the water is completely removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam to improve the surface properties and enhance the bonding ability with the hole transport layer. The vacuum degree of the vacuum evaporator is then maintained at 1x10 -6 torr to 3x10 -7 torr, and deposit various organic materials and metal materials in sequence on the ITO substrate to obtain the OLED devices of the embodiment and the comparative example.

[0203] In each layer of the above-mentioned OLED device, HAT is used to form HI-1 and HID; HI-2 is used to form HI-2; HT-1 and HT-2 are used to form HTL-1 and HTL-2; Liq is used to form ETD and EIL; ET is the main material for forming ETL; the novel compound of the embodiment and the compound of the comparative example are used to form BEL; BD can be used as a dopant of BEL. The detailed structural formulas of the above-mentioned compounds are listed in Table 1 below.

[0204] Table 1

[0205]

[0206] The luminescent materials prepared in the above Examples 1-8 and Comparative Examples 1-2 are used to prepare BEL in an OLED device, as shown in Table 2.

[0207] Table 2

[0208]

[0209] Table 3 below shows the materials, thickness, doping ratio and coating sequence of each organic layer of the OLED device in this test case.

[0210] Table 3

[0211] Organic layer HI-1 HI-2 HID HTL1 HTL2 BEL BD ET1 ETD EIL Cthd Material HAT HI-2 HAT HT1 HT2 BH BD ET1 Liq Liq A1 Thickness(nm) 10 50 / 10 10 20 / 20 / 20 150 Mixing ratio / / 5.00％ / / / 3.00％ / 30％ / / Coating order 1 2 2 3 4 5 5 6 6 7 8

[0212] Evaluation of OLED device: To evaluate the performance of the OLED device, the OLED device was connected to a power supply (brand: Keithley; model: 2400) and tested with a PR650 luminance meter. The OLED device was tested at a brightness of 1000 nits. The test results are shown in Table 4.

[0213] Table 4

[0214]

[0215] It can be seen from the results in Table 4 that compared with the comparative example, the material prepared in the implementation case of the present application is used in an organic electroluminescent device, which can effectively reduce the driving voltage, improve the current efficiency, and increase the service life, and is a blue light material with good performance.

[0216] The technical features of the above-described embodiments may be arbitrarily combined. To make the description concise, not all possible combinations of the technical features in the above-described embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0217] The above-mentioned embodiments only express several implementation methods of the present invention, and the descriptions thereof are relatively specific and detailed, but they cannot be understood as limiting the scope of the invention patent. It should be pointed out that, for ordinary technicians in this field, several variations and improvements can be made without departing from the concept of the present invention, and these all belong to the protection scope of the present invention. Therefore, the protection scope of the patent of the present invention shall be subject to the attached claims.

Claims

1. A phenanthrene-containing organic electroluminescent material, characterized in that: Its structure is shown below: Wherein, Ar is selected from aromatic groups having 6 to 18 carbon atoms in the ring.

2. The phenanthrene-containing organic electroluminescent material according to claim 1, characterized in that: Ar is selected from deuterated aromatic groups having 6 to 18 ring carbon atoms.

3. The phenanthrene-containing organic electroluminescent material according to claim 1, characterized in that: Ar is selected from deuterium-free aromatic groups having 6 to 18 ring carbon atoms.

4. The phenanthrene-containing organic electroluminescent material according to claim 1, characterized in that: Ar is selected from 5. The phenanthrene-containing organic electroluminescent material according to claim 1, characterized in that: It is one of the compounds represented by the following structural formula:

6. A method for preparing a phenanthrene-containing organic electroluminescent material as claimed in any one of claims 1 to 5, characterized in that: Its synthetic route is as follows: Wherein, Ar is selected from aromatic groups having 6 to 18 carbon atoms in the ring.

7. The method for preparing a phenanthrene-containing organic electroluminescent material according to claim 6, characterized in that: The preparation method of the compound A is as follows: 1-bromo-4-chloro-2-fluorobenzene is subjected to n-butyl lithium extraction of bromine, and then reacted with tri-n-butyl borate to obtain product one; product one is subjected to 2-bromo-3-methoxyphenanthrene and palladium acetate reaction to obtain product two; product two is dissolved in DCM, and BBr3 is added for demethylation to obtain product three; product three is dissolved in NMP, and potassium carbonate is added for reaction to obtain product four; product four is reacted with bipyralidone to obtain compound A.

8. The method for preparing a phenanthrene-containing organic electroluminescent material according to claim 6, characterized in that: The preparation method of the compound B is as follows: o-fluoronitrobenzene is reacted with p-bromoaniline to obtain product 1; product 1 is reduced with sodium dithionite to obtain product 2; aromatic acetone is reacted with sodium sulfite to obtain product 3; product 2 is reacted with product 3 to obtain product 4; product 4 is reacted with biboric acid pinacol ester to obtain compound B.

9. Use of the phenanthrene-containing organic electroluminescent material according to any one of claims 1 to 5 in an organic electroluminescent device.

10. An organic electroluminescent device comprising an organic light-emitting layer, characterized in that: The organic light-emitting layer is made of the phenanthrene-containing organic electroluminescent material according to any one of claims 1 to 5.

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