A kind of luminescence auxiliary material and its preparation method and application

Abstract

The present invention provides a luminescent auxiliary material and a preparation method and application thereof. The general structural formula is shown in the specification. The luminescent auxiliary material provided by the present invention is connected with an aromatic amine group and an adamantyl group through a phenyl group with a bridging π group, with dibenzofuran, dibenzothiophene, carbazole, and dimethylfluorene as the skeleton. Among them, adamantane has high spatial symmetry and rigid structure. Introducing it into a condensed ring unit can effectively improve the thermal stability of the material. At the same time, the introduction of the adamantane building unit significantly improves the physical and chemical properties of the material, which is conducive to improving the performance of the device and extending the life of the device. The aromatic amine group makes it have a strong hole transport ability, and the triarylamine structure can reduce the crystallinity of the molecule, reduce the planarity of the molecule, and prevent the molecule from moving on the plane. At the same time, the high hole transport rate can reduce the driving voltage of the device and improve the efficiency and life of the organic electroluminescent device.

Description

Technical Field

[0001] The present invention relates to the technical field of organic photoelectric materials, and in particular to a luminescent auxiliary material and a preparation method and application thereof. Background Art

[0002] Since 2000, organic electroluminescent devices (OLEDs) have received great attention. With rapid development, they have been widely used in display, lighting and other fields due to their advantages such as self-luminescence, high luminous efficiency, full-color display, low power consumption and low driving voltage. Organic electroluminescence uses the optoelectronic functional characteristics of organic semiconductor materials to directly convert electrical energy into light energy. It belongs to the carrier injection type of luminescence. The holes injected from the anode and the electrons injected from the cathode are combined in the light-emitting layer to form excitons, and release energy in the form of light energy. OLED devices are structurally divided into single-layer device structures, double-layer device structures, three-layer and multi-layer device structures. The most widely used one is the three-layer device structure, which has multiple functional layers such as electron transport layer, light-emitting layer and hole transport layer at the same time. The three functional layers perform their respective functions to optimize their performance.

[0003] The hole transport layer (HTL) is responsible for regulating the injection speed and amount of holes. However, most of the current hole transport layer materials will cause thermal stress between the anode and the hole injection layer when the OLED is driven at high current, and the thermal stress significantly reduces the service life of the device. Since the organic materials used in the hole transport region have very high hole mobility, the hole-electron charge balance may be destroyed and the quantum efficiency (cd / A) may be reduced.

[0004] In order to solve the above problems, a luminescent auxiliary layer is generally added between the hole transport layer and the light-emitting layer (i.e., the multi-layer hole transport layer mentioned above is set) to improve the device life and efficiency. The luminescent auxiliary layer can increase the hole utilization rate, thereby improving the luminous efficiency and life, and reducing the driving voltage. However, there are fewer materials for the luminescent auxiliary layer and it faces the problem of unclear gain effect. It is urgent to develop organic functional materials with higher performance.

[0005] Therefore, developing a luminescent auxiliary material that can significantly improve the life of blue light devices while also improving the luminous efficiency, BI value, and driving voltage to a certain extent is a technical problem that people in this field urgently need to solve. Summary of the invention

[0006] In view of this, the present invention provides a luminescence auxiliary material and a preparation method and application thereof.

[0007] The luminescent auxiliary material provided by the present invention can significantly increase the life of the blue light device, while also improving the luminous efficiency, BI value and driving voltage to a certain extent.

[0008] In order to achieve the above object, the present invention adopts the following technical solution:

[0009] A luminescence auxiliary material, the general structural formula of the luminescence auxiliary material is shown in Formula I:

[0010]

[0011] in,

[0012] Ring B is selected from an aryl group having 6 to 20 carbon atoms;

[0013] X is selected from O, -NR 2 ,-C(R 3 )(R 4 )-or S;

[0014] R 1 is selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted 3 to 30-membered heteroaryl group;

[0015] R 2 is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted 3 to 30-membered heteroaryl group;

[0016] R 3 -R 4 Each independently selected from a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted 3 to 30-membered heteroaryl group;

[0017] Ar 1 ,Ar 2 Each is independently selected from a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 3 to 30 carbon atoms, wherein the heteroatom is selected from N, O, S, Si, P or Se; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, wherein the heteroatom is selected from N, O, S, Si, P or Se; a substituted or unsubstituted fused ring group having 10 to 30 carbon atoms, or a substituted or unsubstituted spiro ring group having 5 to 30 carbon atoms.

[0018] Furthermore, the structural formula of the above-mentioned luminescence auxiliary material is selected from any one of the following structural formulas:

[0019]

[0020] Furthermore, the above-mentioned ring B is a phenyl group.

[0021] Furthermore, the above R 1Any one of hydrogen, methyl, ethyl, tert-butyl, methylbenzene, methoxy, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, carbazolyl, fluorenyl, dimethylfluorene, benzofuran, benzothiophene, and pyridyl;

[0022] The above R 2 It is any one of phenyl, naphthyl, biphenyl, phenanthryl, carbazolyl, fluorenyl, dimethylfluorene, terphenyl, benzofuran, benzothiophene and pyridyl.

[0023] Furthermore, the above R 3 -R 4 Each is independently selected from methyl, ethyl, phenyl, methylbenzene, biphenyl or naphthyl.

[0024] Furthermore, the above Ar 1 with Ar 2 Connect with N at any connectable position, Ar 1 ,Ar 2 Each independently selected from the following groups:

[0025]

[0026] Furthermore, the structural formula of the above-mentioned luminescence auxiliary material is selected from any one of the following structural formulas:

[0027]

[0028] In the present specification, the term "substituted or unsubstituted" means substituted by one, two or more substituents selected from the following: deuterium; a halogen group; a nitrile group; a silyl group; a boron group; a C1-C6 alkyl group; a C3-C10 cycloalkyl group; a C6-C18 aryl group; a C3-C30 heterocyclic group, or substituted by a substituent in which two or more substituents are connected among the substituents shown above, or having no substituent.

[0029] Furthermore, the structural formula of the above-mentioned luminescence auxiliary material is selected from any one of the following structural formulas:

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045] The present invention also provides a method for preparing the above-mentioned luminescence auxiliary material, comprising the following steps:

[0046] (1) Under the protection of nitrogen, reactant AI, reactant BI, tetrakis(triphenylphosphine)palladium and potassium carbonate are added to a mixed solvent of toluene, ethanol and water respectively, and the temperature is raised to react. After the reaction is completed, the mixture is cooled to room temperature, and after solid precipitation is completed, the mixture is filtered by suction, and then washed with water to remove salt, and then rinsed with ethanol. The filter cake is dried and recrystallized in 1,4-dioxane to obtain the compound represented by intermediate CI;

[0047] (2) After adding the intermediate CI and the reactant DI into the reaction vessel and dissolving them in toluene, Pd 2 (dba) 3 、P(t-Bu) 3 , t-BuONa; after adding, the reaction temperature is slowly raised, and the mixture is stirred; diatomaceous earth is used for hot filtration to remove salt and catalyst, and the filtrate is cooled to room temperature, and then distilled water is added to the filtrate for washing, and the organic phase is retained after separation, and the aqueous phase is extracted with ethyl acetate; then the combined organic layer is dried with magnesium sulfate, and the solvent is removed with a rotary evaporator; dichloromethane and petroleum ether are used as eluents, and the remaining substance is purified by column chromatography to obtain the compound intermediate EI;

[0048] (3) After adding the intermediate EI and the reactant FI into the reaction vessel and dissolving them in toluene, Pd 2 (dba) 3 、P(t-Bu) 3, t-BuONa; after adding, the reaction temperature is slowly raised, and the mixture is stirred; diatomaceous earth is used for hot filtration to remove salt and catalyst, and after the filtrate is cooled to room temperature, distilled water is then added to the filtrate for washing, and the organic phase is retained after separation, and the aqueous phase is extracted with ethyl acetate; the combined organic layer is then dried with magnesium sulfate, and the solvent is removed with a rotary evaporator; dichloromethane and petroleum ether are used as eluents, and the remaining substance is purified by column chromatography to obtain a luminescent auxiliary material shown in general formula I;

[0049] Hal 2 Any one of chlorine, bromine, or iodine;

[0050] The synthesis route of the luminescent auxiliary material shown in the above general formula I is:

[0051]

[0052] Furthermore, in step (1), the molar ratio of the reactant AI, reactant BI, tetrakis(triphenylphosphine)palladium and potassium carbonate is 1:(1.1-1.2):(0.01-0.02):(2.0-2.3).

[0053] Furthermore, in step (1), the volume ratio of the toluene, ethanol and water is (2-4):1:1.

[0054] Furthermore, in step (1), the temperature is raised to 80-100° C. and the reaction is carried out for 8-12 hours.

[0055] Further, in step (2), the intermediate CI, reactant DI, Pd 2 (dba) 3 、P(t-Bu) 3 , and t-BuONa have a molar ratio of 1.0:(1.0-1.4):0.01:(0.02-0.04):(2.0-2.4).

[0056] Furthermore, in step (2), the volume ratio of the dichloromethane to petroleum ether is 1:(1-9).

[0057] Furthermore, in step (2), the reaction temperature is slowly raised to 105-115° C., and the mixture is stirred for 8-12 h.

[0058] Further, in step (3), the intermediate EI, reactant FI, Pd 2 (dba) 3 、P(t-Bu) 3 , and t-BuONa have a molar ratio of 1.0:(1.0-1.4):0.01:(0.02-0.04):(2.0-2.4).

[0059] Furthermore, in step (3), the volume ratio of the dichloromethane to petroleum ether is 1:(2-7).

[0060] Further, in step (3), the reaction temperature is slowly raised to 105-115° C., and the mixture is stirred for 8-12 h.

[0061] Furthermore, the preparation method of the intermediate BI comprises the following steps:

[0062] 1) Under nitrogen protection, reactant 1 was added to tetrahydrofuran, the temperature was lowered, and n-BuLi was slowly added dropwise to obtain a reaction solution of intermediate 2;

[0063] 2) Under nitrogen protection, the reaction solution containing intermediate 2, reactant 3, palladium acetate (Pd(OAc) 2 ), 2-cyclohexyl-2,4,6-triisopropylbiphenyl (X-Phos), cesium carbonate was dissolved in tetrahydrofuran, heated, reacted, cooled to room temperature, and H 2 O, liquid separation, the organic layer is removed by a rotary evaporator to remove the solvent, the obtained solid is heated and dissolved with toluene, and passed through a silica gel funnel while hot, methanol and dichloromethane are used as developing solvents, the obtained rotary evaporator is removed the solvent, and the obtained solid is dried to obtain intermediate 4;

[0064] 3) Under nitrogen protection, the intermediate 4 is dissolved in THF and cooled, and n-BuLi is slowly added dropwise to react, and the temperature is raised to room temperature. The reactant 5 is placed in a triisopropyl borate mixed solvent, and fully reacted overnight. Hydrochloric acid is added to adjust the pH value of the solution to between 1 and 2 for acidification, and the liquids are separated. After the organic phases are combined, they are dried using anhydrous magnesium sulfate, and the solvent is removed using a rotary evaporator to obtain a solid organic matter. The solid organic matter is completely dissolved using dichloromethane, and then slowly added dropwise to a petroleum ether solution, stirred evenly, a precipitate is precipitated, and the solid is filtered to obtain the solid, which is sequentially rinsed with anhydrous ethanol and petroleum ether, and dried to obtain the reactant BI;

[0065] Hal 1 Any one selected from chlorine, bromine and iodine;

[0066] The synthetic route of intermediate BI is as follows:

[0067]

[0068] Furthermore, in step 1), the molar ratio of the reactant 1 to n-BuLi is 1.0:(1.1-1.5).

[0069] Furthermore, in step 1), the temperature is lowered to -78°C.

[0070] Furthermore, in step 2), the molar ratio of the intermediate 2, reactant 3, palladium acetate, 2-cyclohexyl-2,4,6-triisopropylbiphenyl and cesium carbonate is 1.0:(1-1.2):(0.01-0.05):(0.01-0.05):(2.0-2.3).

[0071] Furthermore, in step 2), the volume ratio of the methanol to dichloromethane is 1:(40-60).

[0072] Furthermore, in step 2), the temperature is raised to 40-70° C. and the reaction is carried out for 2-8 hours.

[0073] Furthermore, in step 3), the molar ratio of the intermediate 4, n-BuLi, and reactant 5 is 1.0:(1.1-1.5):(1.1-1.4).

[0074] In the above terms of the present invention, "slow heating" means adjusting the heating rate according to actual operating conditions, and its slowness is conducive to sufficient reaction and smooth reaction.

[0075] The present invention also provides a use of the above-mentioned luminescence auxiliary material or the luminescence auxiliary material prepared by the above-mentioned method in preparing an organic electroluminescent device.

[0076] Furthermore, the organic electroluminescent device includes a first electrode, a second electrode disposed opposite to the first electrode, and one or more organic layers between the first electrode and the second electrode, and at least one of the organic layers contains the luminescence-assisting material.

[0077] Furthermore, the organic layer may include one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a luminescence auxiliary layer, a luminescent layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0078] Furthermore, the organic layer may be composed of the same substance or different substances.

[0079] Furthermore, when manufacturing an organic electroluminescent device, the above-mentioned light-emitting auxiliary material is used to prepare an organic layer by vacuum evaporation or solution coating.

[0080] Furthermore, the solution coating method is any one of spin coating, dip coating, blade coating, inkjet printing, screen printing, spraying or roller coating.

[0081] Furthermore, the organic electroluminescent device is of top emission type, bottom emission type or bidirectional emission type.

[0082] Furthermore, the organic electroluminescent device is used to prepare an organic light-emitting device, an organic solar cell, an electronic paper, an organic photoreceptor or an organic thin film transistor.

[0083] The beneficial effects of the present invention are as follows: the present invention uses dibenzofuran, dibenzothiophene, carbazole, and dimethylfluorene as the skeleton and connects the aromatic amine group and the adamantyl group through a phenyl group with a bridging π group, wherein adamantane has high spatial symmetry and a rigid structure, and its introduction into the condensed ring unit can effectively improve the thermal stability of the material. At the same time, the introduction of the adamantane building unit significantly improves the physical and chemical properties of the material, which is beneficial to improving the device performance and extending the device life.

[0084] The aromatic amine group gives it a strong hole transport ability. The triarylamine structure can reduce the crystallinity of the molecule, reduce the planarity of the molecule, and prevent the molecule from moving on the plane. At the same time, the high hole transport rate can reduce the driving voltage of the device and improve the efficiency and life of the organic electroluminescent device. BRIEF DESCRIPTION OF THE DRAWINGS

[0085] Attached Figure 1 is the H NMR spectrum of compound 22;

[0086] Attached Figure 2 This is the hydrogen nuclear magnetic resonance spectrum of compound 41. DETAILED DESCRIPTION

[0087] The following embodiments are intended to explain the present invention in detail, and are only preferred embodiments of the present invention, and are not intended to limit the present invention. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in the field without creative work are within the scope of protection of the present invention.

[0088] The synthetic route of reactant B-1 is as follows:

[0089]

[0090] CAS: Reactant b-1: 397243-08-2

[0091] CAS: Reactant b-3: 13101-40-1

[0092] Step 1:

[0093] Under nitrogen protection, reactant b-1 (400 mmol) was added to tetrahydrofuran, the temperature was lowered to -78°C, and n-BuLi (440 mmol) was slowly added dropwise to obtain a reaction solution of intermediate b-2;

[0094] Step 2:

[0095] Under nitrogen protection, the reaction solution containing intermediate b-2 (400 mmol), reactant b-3 (480 mmol), palladium acetate (Pd(OAc) 2)(4mmol), 2-cyclohexyl-2,4,6-triisopropylbiphenyl (X-Phos) (8mmol), cesium carbonate (840mmol) were dissolved in tetrahydrofuran, heated to 50°C, reacted for 4h, cooled to room temperature, and H 2 O, liquid separation, the organic layer was removed by a rotary evaporator to remove the solvent, the obtained solid was heated and dissolved with toluene, and passed through a silica gel funnel while hot, and methanol: dichloromethane volume ratio of 1: (40-60) was used as a developing solvent, and the obtained rotary evaporator was used to remove the solvent, and the obtained solid was dried to obtain intermediate b-4 (45.62 g, Mw: 325.91, yield: 35%);

[0096] Step 3:

[0097] Under nitrogen protection, the intermediate b-4 (140mmol) was dissolved in 1400ml of THF and cooled to -78°C, and n-BuLi (154mmol) was slowly added dropwise, reacted for 2h, and warmed to room temperature. The reactant b-5 (154mmol) (triisopropyl borate) was added to a mixed solvent, and fully reacted overnight. Hydrochloric acid was added, and the pH value of the solution was adjusted to between 1 and 2 for acidification. After separation and merging the organic phases, anhydrous magnesium sulfate was used for drying, and a rotary evaporator was used to remove the solvent to obtain a solid organic matter. The solid organic matter was completely dissolved in dichloromethane, and then slowly added dropwise to the petroleum ether solution, stirred evenly, and a precipitate was precipitated. The solid was filtered to obtain the solid, and then rinsed with anhydrous ethanol and petroleum ether in turn, and dried to obtain the reactant B-1 (34.20g, Mw: 290.87, yield: 84%).

[0098] Example 1: Synthesis of Compound 1

[0099]

[0100] Step 1:

[0101] Under the protection of nitrogen, reactant A-1 (100 mmol), reactant B-1 (110 mmol), tetrakis(triphenylphosphine)palladium (1 mmol) and potassium carbonate (210 mmol) were added to a mixed solvent of toluene (4 ml), ethanol (200 ml) and water (200 ml), respectively, and the temperature was raised to 95°C. The reaction was carried out for 8 hours. After the reaction was completed, the mixture was cooled to room temperature. After the solid was precipitated, it was filtered off by suction, then washed with water to remove the salt, and then rinsed with ethanol. The filter cake was dried and recrystallized in 1,4-dioxane to obtain the compound represented by intermediate C-1 (23.13 g, yield: 56%, Mw: 413.12).

[0102] Step 2:

[0103] After intermediate C-1 (40 mmol) and reactant D-1 (46 mmol) were added to the reaction vessel and dissolved in toluene, Pd was added under nitrogen protection. 2 (dba) 3 (0.4mmol), P(t-Bu) 3 (0.8mmol), t-BuONa (80mmol); after adding, the reaction temperature was slowly raised to 110°C, and the mixture was stirred for 8h; diatomaceous earth was used for hot filtration to remove salt and catalyst, and the filtrate was cooled to room temperature, and then distilled water was added to the filtrate for washing, and the organic phase was retained after separation, and the aqueous phase was extracted with ethyl acetate; the combined organic layer was then dried over magnesium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography using dichloromethane and petroleum ether in a volume ratio of 1: (1-9) as eluent to obtain compound intermediate E-1 (18.36g, yield: 82%, Mw: 559.86).

[0104] Step 3:

[0105] After adding intermediate E-1 (30 mmol) and reactant F-1 (36 mmol) into a reaction vessel and dissolving in toluene, Pd 2 (dba) 3 (0.3mmol), P(t-Bu) 3 (0.6mmol), t-BuONa (60mmol); after adding, the reaction temperature was slowly raised to 105°C, and the mixture was stirred for 12h; diatomaceous earth was used for hot filtration to remove salt and catalyst, and the filtrate was cooled to room temperature, and then distilled water was added to the filtrate for washing, and the organic phase was retained after separation, and the aqueous phase was extracted with ethyl acetate; the combined organic layer was then dried over magnesium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography using dichloromethane and petroleum ether in a volume ratio of 1: (2-7) as eluent to obtain compound 1 (18.58g, yield: 87%, Mw: 712.08).

[0106] The yield in each of the above steps is the fractional yield of the corresponding step.

[0107] Characterization:

[0108] HPLC purity: >99.7%.

[0109] Mass spectrometry test: theoretical value is 711.91; tested value is 712.08.

[0110] Elemental Analysis:

[0111] Theoretical values: C, 87.73; H, 5.81; N, 1.97; O, 4.49

[0112] Test values: C, 87.62; H, 5.92; N, 2.05; O, 4.58

[0113] Example 2: Synthesis of Compound 22

[0114] Step 1:

[0115] The reaction was consistent with that of intermediate C-1 in Example 1 to obtain intermediate C-22;

[0116] Step 2:

[0117] After intermediate C-22 (42 mmol) and reactant D-22 (54.6 mmol) were added to the reaction vessel and dissolved in toluene, Pd was added under nitrogen protection. 2 (dba) 3 (0.42mmol), P(t-Bu) 3 (1.05mmol), t-BuONa (88.2mmol); after adding, the reaction temperature was slowly raised to 105°C, and the mixture was stirred for 12h; diatomaceous earth was used for hot filtration to remove salt and catalyst, and the filtrate was cooled to room temperature, and then distilled water was added to the filtrate for washing, and the organic phase was retained after separation, and the aqueous phase was extracted with ethyl acetate; then the combined organic layer was dried with magnesium sulfate, and the solvent was removed with a rotary evaporator; dichloromethane and petroleum ether in a volume ratio of 1: (1-9) were used as eluents, and the remaining substance was purified by column chromatography to obtain compound intermediate E-22 (21.34g, yield: 86.7%, Mw: 586.02);

[0118] Step 3:

[0119] After adding intermediate E-22 (30 mmol) and reactant F-22 (39 mmol) into the reaction vessel and dissolving in toluene, Pd 2 (dba) 3 (0.3mmol), P(t-Bu) 3 (1.2mmol), t-BuONa (63mmol); after adding, the reaction temperature was slowly raised to 115°C, and the mixture was stirred for 9h; diatomaceous earth was used for hot filtration to remove salt and catalyst, and the filtrate was cooled to room temperature, and then distilled water was added to the filtrate for washing, and the organic phase was retained after separation, and the aqueous phase was extracted with ethyl acetate; the combined organic layer was then dried over magnesium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography using dichloromethane and petroleum ether in a volume ratio of 1: (2-7) as eluent to obtain compound 22 (19.38g, yield: 85.9%, Mw: 752.23).

[0120] The yield in each of the above steps is the fractional yield of the corresponding step.

[0121] Characterization:

[0122] HPLC purity: >99.8%.

[0123] Mass spectrometry test: theoretical value is 751.97; tested value is 752.23.

[0124] Elemental Analysis:

[0125] Theoretical values: C, 87.85; H, 6.03; N, 1.86; O, 4.26

[0126] Test values: C, 87.59; H, 6.24; N, 1.92; O, 4.38

[0127] H NMR spectrum: as attached Figure 1 shown.

[0128] Example 3: Synthesis of Compound 41

[0129]

[0130] Step 1:

[0131] The reaction was consistent with that of intermediate C-1 in Example 1 to obtain intermediate C-41;

[0132] Step 2:

[0133] After intermediate C-41 (42 mmol) and reactant D-41 (54.6 mmol) were added to the reaction vessel and dissolved in toluene, Pd was added under nitrogen protection. 2 (dba) 3 (0.42mmol), P(t-Bu) 3 (1.05mmol), t-BuONa (88.2mmol); after adding, the reaction temperature was slowly raised to 105°C, and the mixture was stirred for 12h; diatomaceous earth was used for hot filtration to remove salt and catalyst, and the filtrate was cooled to room temperature, and then distilled water was added to the filtrate for washing, and the organic phase was retained after separation, and the aqueous phase was extracted with ethyl acetate; then the combined organic layer was dried with magnesium sulfate, and the solvent was removed with a rotary evaporator; dichloromethane and petroleum ether in a volume ratio of 1: (1-9) were used as eluents, and the remaining substance was purified by column chromatography to obtain compound intermediate E-41 (21.2g, yield: 84.7%, Mw: 595.97);

[0134] Step 3:

[0135] After adding intermediate E-41 (30 mmol) and reactant F-41 (39 mmol) into a reaction vessel and dissolving in toluene, Pd 2 (dba) 3 (0.3mmol), P(t-Bu) 3 (1.2mmol), t-BuONa (63mmol); after adding, the reaction temperature was slowly raised to 115°C, and the mixture was stirred for 9h; diatomaceous earth was used for hot filtration to remove salt and catalyst, and the filtrate was cooled to room temperature, and then distilled water was added to the filtrate for washing, and the organic phase was retained after separation, and the aqueous phase was extracted with ethyl acetate; the combined organic layer was then dried over magnesium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography using dichloromethane and petroleum ether in a volume ratio of 1: (2-7) as eluent to obtain compound 41 (18.4g, yield: 82%, Mw: 748.34).

[0136] The yield in each of the above steps is the fractional yield of the corresponding step.

[0137] Characterization:

[0138] HPLC purity: >99.8%.

[0139] Mass spectrometry test: theoretical value is 747.98; tested value is 748.34.

[0140] Elemental Analysis:

[0141] Theoretical values: C, 89.92; H, 6.06; N, 1.87; O, 2.14

[0142] Test values: C, 89.61; H, 6.28; N, 1.95; O, 2.28

[0143] H NMR spectrum: as attached Figure 2 shown.

[0144] Example 4: Synthesis of Compound 52

[0145]

[0146] Step 1:

[0147] The reaction was consistent with that of intermediate C-1 in Example 1 to obtain intermediate C-52;

[0148] Step 2:

[0149] After intermediate C-52 (30 mmol) and reactant D-52 (36 mmol) were added to the reaction vessel and dissolved in toluene, Pd was added under nitrogen protection. 2 (dba)3 (0.3mol), P(t-Bu) 3 (0.6mmol), t-BuONa (66mmol); after adding, the reaction temperature was slowly raised to 105°C, and the mixture was stirred for 12h; diatomaceous earth was used for hot filtration to remove salt and catalyst, and the filtrate was cooled to room temperature, and then distilled water was added to the filtrate for washing, and the organic phase was retained after separation, and the aqueous phase was extracted with ethyl acetate; then the combined organic layer was dried with magnesium sulfate, and the solvent was removed with a rotary evaporator; dichloromethane and petroleum ether in a volume ratio of 1: (1-9) were used as eluents, and the remaining substance was purified by column chromatography to obtain compound intermediate E-52 (15.20g, yield: 85%, Mw: 595.94);

[0150] Step 3:

[0151] After adding intermediate E-52 (20 mmol) and reactant F-52 (26 mmol) into the reaction vessel and dissolving in toluene, Pd 2 (dba) 3 (0.2mmol), P(t-Bu) 3 (0.8mmol), t-BuONa (44mmol); after adding, the reaction temperature was slowly raised to 110°C, and the mixture was stirred for 10h; diatomaceous earth was used for hot filtration to remove salt and catalyst, and the filtrate was cooled to room temperature, and then distilled water was added to the filtrate for washing, and the organic phase was retained after separation, and the aqueous phase was extracted with ethyl acetate; the combined organic layer was then dried over magnesium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography using dichloromethane and petroleum ether in a volume ratio of 1: (2-7) as eluent to obtain compound 52 (13.55g, yield: 88.9%, Mw: 762.25).

[0152] The yield in each of the above steps is the fractional yield of the corresponding step.

[0153] Characterization:

[0154] HPLC purity: >99.7%.

[0155] Mass spectrometry test: theoretical value is 761.97; tested value is 762.25.

[0156] Elemental Analysis:

[0157] Theoretical values: C, 88.27; H, 5.69; N, 1.84; O, 4.20

[0158] Test values: C, 88.06; H, 5.83; N, 1.91; O, 4.31

[0159] Example 5: Synthesis of Compound 188

[0160] The synthetic route of reactant B-188 is as follows:

[0161]

[0162] CAS: Reactant b-8: 148836-41-3

[0163] Step 1:

[0164] Under nitrogen protection, add reactant b-6 (400 mmol) to tetrahydrofuran, cool to -78°C, and slowly drop n-BuLi (440 mmol) to obtain a reaction solution of intermediate b-7;

[0165] Step 2:

[0166] Under nitrogen protection, the reaction solution containing intermediate b-7 (400 mmol), reactant b-8 (480 mmol), palladium acetate (Pd(OAc) 2 )(4mmol), 2-cyclohexyl-2,4,6-triisopropylbiphenyl (X-Phos) (8mmol), cesium carbonate (840mmol) were dissolved in tetrahydrofuran, heated to 50°C, reacted for 4h, cooled to room temperature, and H 2 O, liquid separation, the organic layer was removed by a rotary evaporator to remove the solvent, the obtained solid was heated and dissolved with toluene, and passed through a silica gel funnel while hot, and methanol: dichloromethane volume ratio of 1: (40-60) was used as a developing solvent, and the obtained rotary evaporator was used to remove the solvent, and the obtained solid was dried to obtain intermediate b-9 (49.54 g, Mw: 325.93, yield: 38%);

[0167] Step 3:

[0168] Under nitrogen protection, the intermediate b-9 (140mmol) was dissolved in 1400ml of THF and cooled to -78°C. n-BuLi (154mmol) was slowly added dropwise, and the reaction was continued for 2h. The mixture was warmed to room temperature. The reactant b-10 (154mmol) (triisopropyl borate) was added to a mixed solvent and fully reacted overnight. Hydrochloric acid was added and the pH value of the solution was adjusted to between 1 and 2 for acidification. The liquid was separated and the organic phase was combined. The mixture was dried with anhydrous magnesium sulfate and the solvent was removed with a rotary evaporator to obtain a solid organic matter. The solid organic matter was completely dissolved with dichloromethane, and then slowly added dropwise to a petroleum ether solution. The mixture was stirred evenly. A precipitate was precipitated. The solid was filtered and washed with anhydrous ethanol and petroleum ether in turn. The reaction product B-188 (32.99g, Mw: 290.89, yield: 81%) was obtained.

[0169]

[0170] Step 1:

[0171] Under the protection of nitrogen, reactant A-188 (100 mmol), reactant B-188 (110 mmol), tetrakis(triphenylphosphine)palladium (1 mmol) and potassium carbonate (210 mmol) were added to a mixed solvent of toluene (4 ml), ethanol (200 ml) and water (200 ml), respectively, and the temperature was raised to 95°C, and the reaction was carried out for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, and after the solid was precipitated, it was filtered by suction, and then washed with water to remove salt, and then rinsed with ethanol, the filter cake was dried, and placed in 1,4-dioxane for recrystallization to obtain the compound represented by intermediate C-188 (24.90 g, yield 51%, Mw: 488.25);

[0172] Step 2:

[0173] After intermediate C-188 (40 mmol) and reactant D-188 (46 mmol) were added to the reaction vessel and dissolved in toluene, Pd was added under nitrogen protection. 2 (dba) 3 (0.4mmol), P(t-Bu) 3 (1.12mmol), t-BuONa (80mmol); after adding, the reaction temperature was slowly raised to 110°C, and the mixture was stirred for 8h; diatomaceous earth was used for hot filtration to remove salt and catalyst, and the filtrate was cooled to room temperature, and then distilled water was added to the filtrate for washing, and the organic phase was retained after separation, and the aqueous phase was extracted with ethyl acetate; then the combined organic layer was dried with magnesium sulfate, and the solvent was removed with a rotary evaporator; dichloromethane and petroleum ether were used as eluents in a volume ratio of 1: (1-9), and the remaining substance was purified by column chromatography to obtain compound intermediate E-188 (21.61g, yield 87%, Mw: 621.03);

[0174] Step 3:

[0175] After adding intermediate E-188 (30 mmol) and reactant F-188 (34.5 mmol) into the reaction vessel and dissolving in toluene, Pd 2 (dba) 3 (0.3mmol), P(t-Bu) 3(0.84mmol), t-BuONa (60mmol); after adding, the reaction temperature was slowly raised to 115°C, and the mixture was stirred for 8.5h; diatomaceous earth was used for hot filtration to remove salt and catalyst, and the filtrate was cooled to room temperature, and then distilled water was added to the filtrate for washing, and the organic phase was retained after separation, and the aqueous phase was extracted with ethyl acetate; then the combined organic layer was dried with magnesium sulfate, and the solvent was removed with a rotary evaporator; the remaining substance was purified by column chromatography using dichloromethane and petroleum ether in a volume ratio of 1: (1-9) as eluent to obtain compound 188 (20.26g, yield: 85.8%, Mw: 787.33)

[0176] The yield in each of the above steps is the fractional yield of the corresponding step.

[0177] Characterization:

[0178] HPLC purity: >99.7%.

[0179] Mass spectrometry test: theoretical value is 787.02; tested value is 787.33.

[0180] Elemental Analysis:

[0181] Theoretical value: C, 88.52; H, 5.89; N, 3.56; O, 2.03

[0182] Test values: C, 88.28; H, 6.10; N, 3.61; O, 2.10

[0183] Example 6: Synthesis of Compound 268

[0184]

[0185] Step 1:

[0186] Under the protection of nitrogen, reactant A-268 (100 mmol), reactant B-268 (110 mmol), tetrakis(triphenylphosphine)palladium (1 mmol) and potassium carbonate (210 mmol) were added to a mixed solvent of toluene (4 ml), ethanol (200 ml) and water (200 ml), respectively, and the temperature was raised to 95°C, and the reaction was carried out for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, and after the solid was precipitated, it was filtered by suction, and then washed with water to remove salt, and then rinsed with ethanol, the filter cake was dried, and placed in 1,4-dioxane for recrystallization to obtain the compound represented by intermediate C-268 (24.16 g, yield: 55%, Mw: 439.26);

[0187] Step 2:

[0188] After intermediate C-268 (42 mmol) and reactant D-268 (46.2 mmol) were added to the reaction vessel and dissolved in toluene, Pd was added under nitrogen protection. 2 (dba) 3 (0.42mmol), P(t-Bu) 3 (1.2mmol), t-BuONa (84mmol); after adding, the reaction temperature was slowly raised to 105°C, and the mixture was stirred for 12h; diatomaceous earth was used for hot filtration to remove salt and catalyst, and the filtrate was cooled to room temperature, and then distilled water was added to the filtrate for washing, and the organic phase was retained after separation, and the aqueous phase was extracted with ethyl acetate; then the combined organic layer was dried with magnesium sulfate, and the solvent was removed with a rotary evaporator; the remaining substance was purified by column chromatography using dichloromethane and petroleum ether in a volume ratio of 1: (1-9) as eluent to obtain compound intermediate E-268 (21.34g, yield: 83%, Mw: 612.05);

[0189] Step 3:

[0190] After adding intermediate E-268 (30 mmol) and reactant F-268 (33 mmol) into the reaction vessel and dissolving in toluene, Pd 2 (dba) 3 (0.3mmol), P(t-Bu) 3 (0.9mmol), t-BuONa (60mmol); after adding, the reaction temperature was slowly raised to 110°C, and the mixture was stirred for 10h; diatomaceous earth was used for hot filtration to remove salt and catalyst, and the filtrate was cooled to room temperature, and then distilled water was added to the filtrate for washing, and the organic phase was retained after separation, and the aqueous phase was extracted with ethyl acetate; the combined organic layer was then dried over magnesium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography using dichloromethane and petroleum ether in a volume ratio of 1: (2-7) as eluent to obtain compound 268 (20.20g, yield: 86.5%, Mw: 778.41).

[0191] The yield in each of the above steps is the fractional yield of the corresponding step.

[0192] Characterization:

[0193] HPLC purity: >99.8%.

[0194] Mass spectrometry test: theoretical value is 778.05; tested value is 778.41.

[0195] Elemental Analysis:

[0196] Theoretical value: C, 89.54; H, 6.61; N, 1.8; O, 2.06

[0197] Test values: C, 89.23; H, 6.84; N, 1.84; O, 2.22

[0198] Example 7: Synthesis of Compound 274

[0199]

[0200] Step 1:

[0201] Under the protection of nitrogen, reactant A-274 (100 mmol), reactant B-274 (110 mmol), tetrakis(triphenylphosphine)palladium (1 mmol) and potassium carbonate (210 mmol) were added to a mixed solvent of toluene (4 ml), ethanol (200 ml) and water (200 ml), respectively, and the temperature was raised to 95°C, and the reaction was carried out for 8 hours. After the reaction was completed, the mixture was cooled to room temperature, and after the solid was precipitated, it was filtered by suction, and then washed with water to remove salt, and then rinsed with ethanol, the filter cake was dried, and placed in 1,4-dioxane for recrystallization to obtain the compound represented by intermediate C-274 (22.32 g, yield: 52%, Mw: 429.22);

[0202] Step 2:

[0203] After intermediate C-274 (40 mmol) and reactant D-274 (46 mmol) were added to the reaction vessel and dissolved in toluene, Pd was added under nitrogen protection. 2 (dba) 3 (0.4mmol), P(t-Bu) 3 (1.12mmol), t-BuONa (80mmol); after adding, the reaction temperature was slowly raised to 110°C, and the mixture was stirred for 8h; diatomaceous earth was used for hot filtration to remove salt and catalyst, and the filtrate was cooled to room temperature, and then distilled water was added to the filtrate for washing, and the organic phase was retained after separation, and the aqueous phase was extracted with ethyl acetate; then the combined organic layer was dried with magnesium sulfate, and the solvent was removed with a rotary evaporator; the remaining substance was purified by column chromatography using dichloromethane and petroleum ether in a volume ratio of 1: (1-9) as eluent to obtain compound intermediate E-274 (28.68g, yield: 83%, Mw: 575.98);

[0204] Step 3:

[0205] After adding intermediate E-274 (30 mmol) and reactant F-274 (33 mmol) into the reaction vessel and dissolving in toluene, Pd 2 (dba) 3(0.3mmol), P(t-Bu) 3 (0.9mmol), t-BuONa (60mmol); after adding, the reaction temperature was slowly raised to 110°C, and the mixture was stirred for 10h; diatomaceous earth was used for hot filtration to remove salt and catalyst, and the filtrate was cooled to room temperature, and then distilled water was added to the filtrate for washing, and the organic phase was retained after separation, and the aqueous phase was extracted with ethyl acetate; the combined organic layer was then dried over magnesium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography using dichloromethane and petroleum ether in a volume ratio of 1: (2-7) as eluent to obtain compound 274 (28.18g, yield: 86%, Mw: 728.16).

[0206] The yield in each of the above steps is the fractional yield of the corresponding step.

[0207] Characterization:

[0208] HPLC purity: >99.7%.

[0209] Mass spectrometry test: theoretical value is 727.97; tested value is 728.16.

[0210] Elemental Analysis:

[0211] Theoretical values: C, 85.80; H, 5.68; N, 1.92; O, 2.20; S, 4.40

[0212] Test values: C, 85.45; H, 5.87; N, 1.99; O, 2.31; S, 4.46

[0213] Embodiment 8-70

[0214] The following compounds were prepared by referring to the synthesis methods of Examples 1-7. The molecular formula and mass spectrum of the compounds are shown in Table 1:

[0215] Table 1 Molecular formula and mass spectrum of compounds of Examples 8-70

[0216]

[0217]

[0218] In addition, it should be noted that other compounds of the present invention can be obtained by referring to the synthesis methods of the above-mentioned embodiments, so they are not listed one by one here.

[0219] [Application Example 1] Preparation of organic electroluminescent devices:

[0220] a. ITO anode: Wash the ITO (indium tin oxide)-Ag-ITO (indium tin oxide) glass substrate with a coating thickness of 150nm in distilled water twice, ultrasonically wash for 30 minutes, and then repeatedly wash it with distilled water twice, ultrasonically wash for 10 minutes. After washing, transfer it to a spin dryer for drying, and finally bake it in a vacuum oven at 220℃ for 2 hours. After baking, cool it down and it can be used. Use this substrate as the anode, use an evaporation machine to carry out the evaporation device process, and evaporate other functional layers on it in sequence.

[0221] b. HIL (hole injection layer): The hole injection layer materials HT and P-dopant are vacuum evaporated at a deposition rate of 98:2, and the thickness is 10 nm;

[0222] c. HTL (hole transport layer): At a deposition rate of 100%, 120 nm of HT was vacuum-deposited on the hole injection layer as a hole transport layer.

[0223] d. Light-emitting auxiliary layer: At a deposition rate of , 10 nm of the compound 1 provided in the above embodiment is vacuum-deposited on the hole transport layer as a light-emitting auxiliary layer;

[0224] e. EML (light-emitting layer): Then on the above-mentioned light-emitting auxiliary layer, The host material (Host) and dopant material (Dopant) with a thickness of 25nm are vacuum-deposited as the light-emitting layer. The chemical formulas of Host and Dopant are shown below. The evaporation rate ratio of Host to Dopant is 97:3.

[0225] f. HB (hole blocking layer): The hole blocking layer with a thickness of 5.0 nm was vacuum-deposited at a deposition rate of . Its chemical formula is shown below.

[0226] g. ETL (Electron Transport Layer): ET and Liq were vacuum-deposited at a deposition rate of 35 nm as an electron transport layer, and the chemical formula of ET is shown below. The deposition rate ratio of ET to Liq is 50:50.

[0227] h. EIL (electron injection layer): At a evaporation rate of , a 1.0 nm Yb film layer was evaporated to form an electron injection layer.

[0228] i. Cathode: The evaporation rate ratio is 1:9, and magnesium and silver are evaporated at 18nm, and the evaporation rate ratio is 1:9 to obtain an OLED device.

[0229] j. Light extraction layer: At a deposition rate of , CPL with a thickness of 70 nm was vacuum-deposited on the cathode as a light extraction layer.

[0230] k. Package the substrate after evaporation. First, use the glue coating equipment to coat the cleaned cover with UV glue, then move the coated cover to the pressing section, place the evaporation-deposited substrate on the upper end of the cover, and finally bond the substrate and cover with the bonding equipment, and complete the light curing of the UV glue.

[0231] Device structure:

[0232] ITO / Ag / ITO / HT:P-dopant(10nm,2%) / HT(120nm) / Compound 1(10nm) / Host:Dopant(25nm,3%) / HB(5nm) / ET:Liq(35nm,50%) / Yb(1nm) / Mg:Ag(18nm,1:9) / CPL(70nm).

[0233]

[0234] [Application Example 2-70]

[0235] The organic electroluminescent devices of Application Examples 2-70 were prepared according to the above-mentioned method for preparing an organic electroluminescent device, except that the compound 1 in Application Example 1 was replaced by a corresponding compound to form a light-emitting auxiliary layer.

[0236] Comparative Example 1

[0237] An organic electroluminescent device was prepared according to the above method for preparing an organic electroluminescent device containing a luminescent auxiliary material, except that the compound in Application Example 1 was replaced by Comparative Compound 1.

[0238] Comparative Example 2

[0239] An organic electroluminescent device was prepared according to the above method for preparing an organic electroluminescent device containing a luminescent auxiliary material, except that the compound in Application Example 1 was replaced by Comparative Compound 2.

[0240] Comparative Example 3

[0241] An organic electroluminescent device was prepared according to the above method for preparing an organic electroluminescent device containing a luminescent auxiliary material, except that the compound in Application Example 1 was replaced by Comparative Compound 3.

[0242] Comparative Example 4

[0243] An organic electroluminescent device was prepared according to the above method for preparing an organic electroluminescent device containing a luminescent auxiliary material, except that the compound in Application Example 1 was replaced by Comparative Compound 4.

[0244] Comparative Example 5

[0245] An organic electroluminescent device was prepared according to the above method for preparing an organic electroluminescent device containing a luminescent auxiliary material, except that the compound in Application Example 1 was replaced by Comparative Compound 5.

[0246] Comparative Example 6

[0247] An organic electroluminescent device was prepared according to the above method for preparing an organic electroluminescent device containing a luminescent auxiliary material, except that the compound in Application Example 1 was replaced by Comparative Compound 6.

[0248] Comparative Example 7

[0249] An organic electroluminescent device was prepared according to the above method for preparing an organic electroluminescent device containing a luminescent auxiliary material, except that the compound in Application Example 1 was replaced by Comparative Compound 7.

[0250] Comparative Example 8

[0251] An organic electroluminescent device was prepared according to the above method for preparing an organic electroluminescent device containing a luminescent auxiliary material, except that the compound in Application Example 1 was replaced by Comparative Compound 8.

[0252] Comparative Example 9

[0253] An organic electroluminescent device was prepared according to the above method for preparing an organic electroluminescent device containing a luminescent auxiliary material, except that the compound in Application Example 1 was replaced by Comparative Compound 9.

[0254] The structural formula of comparative compound 1-9 is as follows:

[0255]

[0256] The driving voltage, luminous efficiency, BI value and life of the organic electroluminescent devices obtained from the device application examples 1 to 70 and the device comparative examples 1 to 9 were characterized at a brightness of 1000 (nits). The test results are shown in Table 2 below:

[0257] Table 2 Luminous characteristics test results (brightness: 1000nits)

[0258]

[0259]

[0260]

[0261] The present invention uses dibenzofuran, dibenzothiophene, carbazole and dimethylfluorene as the skeleton and connects the phenyl with the bridging π group with the aromatic amine group and the adamantyl group. The adamantane has high spatial symmetry and rigid structure. The introduction of the adamantane building unit can effectively improve the thermal stability of the material. At the same time, the introduction of the adamantane building unit significantly improves the physical and chemical properties of the material, thereby obtaining an organic electroluminescent compound with excellent performance for a blue light emitting auxiliary layer.

[0262] As can be seen from the table above, the performance of the light-emitting auxiliary material devices used in Comparative Example 1-9 and Application Example 1-70 has been significantly improved in lifespan, and the luminous efficiency, BI value, and driving voltage have also been improved to a certain extent.

[0263] From the experimental data, the main difference between compound 35 and comparative examples 2 and 3 is the use of adamantane, which extends the life of the blue light device by about 60 hours, an increase of nearly 40%. Compared with the comparative compounds, other compounds of the present invention containing adamantane generally increase the life by about 20-40%, which has achieved a significant improvement in the blue light life.

[0264] In this field, the problem of short life of blue light devices has always been one of the problems that technicians in this field need to solve urgently. The adamantane in the present invention can significantly improve the structural stability of the compound and significantly increase the life of the blue light device, which is conducive to application in actual production.

[0265] The above description of the disclosed embodiments enables one skilled in the art to implement or use the present invention. Various modifications to these embodiments will be apparent to one skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the present invention. Therefore, the present invention will not be limited to the embodiments shown herein, but rather to the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. A luminescent auxiliary material, characterized in that: The structural formula of the luminescence auxiliary material is selected from any one of the following structural formulas:

2. A method for preparing the luminescence auxiliary material as claimed in claim 1, characterized in that: The following steps are involved: (1) Under the protection of nitrogen, reactant AI, reactant BI, tetrakis(triphenylphosphine)palladium and potassium carbonate are added to a mixed solvent of toluene, ethanol and water respectively, and the temperature is raised to react. After the reaction is completed, the mixture is cooled to room temperature, and after solid precipitation is completed, the mixture is filtered by suction, and then washed with water to remove salt, and then rinsed with ethanol. The filter cake is dried and recrystallized in 1,4-dioxane to obtain the compound represented by intermediate CI; (2) After adding the intermediate CI and the reactant DI to a reaction vessel and dissolving them in toluene, Pd2(dba)3, P(t-Bu)3, and t-BuONa are added under nitrogen protection; after the addition, the reaction temperature is slowly increased, and the mixture is stirred; diatomaceous earth is used for hot filtration to remove salts and catalysts, and after the filtrate is cooled to room temperature, distilled water is then added to the filtrate for washing, and after separation, the organic phase is retained, and the aqueous phase is extracted with ethyl acetate; the combined organic layer is then dried with magnesium sulfate, and the solvent is removed using a rotary evaporator; The remaining substance was purified by column chromatography using dichloromethane and petroleum ether as eluents to obtain compound intermediate EI; (3) After adding the intermediate EI and the reactant FI to a reaction vessel and dissolving them in toluene, Pd2(dba)3, P(t-Bu)3, and t-BuONa are added under nitrogen protection; after the addition, the reaction temperature is slowly increased, and the mixture is stirred; diatomaceous earth is used for hot filtration to remove salts and catalysts, and after the filtrate is cooled to room temperature, distilled water is added to the filtrate for washing, and after separation, the organic phase is retained, and the aqueous phase is extracted with ethyl acetate; the combined organic layer is then dried with magnesium sulfate, and the solvent is removed using a rotary evaporator; Using dichloromethane and petroleum ether as eluents, purifying the remaining substance by column chromatography to obtain the luminescent auxiliary material represented by general formula I; Hal2 is any one of chlorine, bromine, or iodine; The synthesis route of the luminescent auxiliary material shown in the general formula I is:

3. The method for preparing the luminescence auxiliary material according to claim 2, characterized in that: The preparation method of the intermediate BI comprises the following steps: 1) Under nitrogen protection, reactant 1 was added to tetrahydrofuran, the temperature was lowered, and n-BuLi was slowly added dropwise to obtain a reaction solution of intermediate 2; 2) Under nitrogen protection, the reaction solution containing intermediate 2, reactant 3, palladium acetate (Pd(OAc)2), 2-cyclohexyl-2,4,6-triisopropylbiphenyl (X-Phos), and cesium carbonate are dissolved in tetrahydrofuran, heated, reacted, cooled to room temperature, H2O is added, separated, the organic layer is removed by a rotary evaporator, the obtained solid is heated and dissolved with toluene, and passed through a silica gel funnel while hot, methanol and dichloromethane are used as developing agents, the obtained rotary evaporator is used to remove the solvent, and the obtained solid is dried to obtain intermediate 4; 3) Under nitrogen protection, the intermediate 4 is dissolved in THF and cooled, and n-BuLi is slowly added dropwise to react, and the temperature is raised to room temperature. The reactant 5 is placed in a triisopropyl borate mixed solvent, and fully reacted overnight. Hydrochloric acid is added to adjust the pH value of the solution to between 1 and 2 for acidification, and the liquids are separated. After the organic phases are combined, they are dried using anhydrous magnesium sulfate, and the solvent is removed using a rotary evaporator to obtain a solid organic matter. The solid organic matter is completely dissolved using dichloromethane, and then slowly added dropwise to a petroleum ether solution, stirred evenly, a precipitate is precipitated, and the solid is filtered to obtain the solid, which is sequentially rinsed with anhydrous ethanol and petroleum ether, and dried to obtain the reactant BI; The Hal1 is any one of chlorine, bromine, or iodine; The synthetic route of intermediate BI is as follows:

4. Use of the luminescence auxiliary material according to claim 1 or the luminescence auxiliary material prepared by the method according to claim 2 or 3 in preparing an organic electroluminescent device.

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