A luminescence assisting material, a preparation method thereof, and an electroluminescent device

Abstract

The present invention discloses a luminescence assisting material, the general structural formula of which is shown in Chemical Formula 1: and a preparation method of the above luminescence assisting material and an electroluminescent device containing the same. By introducing triarylamine functional groups, the present invention greatly improves the hole transport efficiency. The amine unit has steric hindrance to prevent electrons from overflowing. Moreover, by introducing a benzodibenzofuran or benzodibenzothiophene structure, the molecular symmetry is reduced, the conformational isomers of the molecule are increased, and the molecule has a rigid planar structure, so that the molecules are not easily crystallized or aggregated, and the yield of manufacturing the organic EL device is improved.

Description

Technical Field

[0001] The present invention relates to the field of organic optoelectronic materials, and more particularly to a luminescence assisting material, a preparation method thereof, and an electroluminescent device. Background Art

[0002] Organic light-emitting diodes (OLEDs) have gradually come into view as a new and promising display technology. An OLED is an electroluminescent device formed by a multi-layer organic thin film structure, in which the organic thin film is a film of an organic light-emitting material formed on a substrate by evaporation, deposition, or spin coating processes.

[0003] In such an organic light-emitting diode, when a voltage is applied between the anode and the cathode, holes from the anode and electrons from the cathode are injected into the organic material layer. The generated excitons emit light with a specific wavelength when migrating to the ground state. It has the following structure: an anode, a cathode, and an organic material layer therebetween. In order to improve the efficiency and stability of the organic EL element, the organic material layer includes multiple layers with different materials, such as a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting layer, an electron transport layer (ETL), and an electron injection layer (EIL). Among them, layers having the function of transporting holes, such as a hole injection layer, a hole transport layer, and an electron blocking layer, can change the hole transport efficiency, light-emitting efficiency, lifetime, etc. of holes to the light-emitting layer, and have a great impact on the performance data of electronic devices.

[0004] The research on organic electroluminescent materials has been widely carried out in the academic and industrial fields. However, so far, an organic layer material for stable and efficient organic electrical components has not been fully developed, and the industrialization process of this technology still faces many key problems. Therefore, how to develop a new luminescence assisting material has always been an urgent problem for those skilled in the art. Summary of the Invention

[0005] In view of this, the technical problem to be solved by the present invention is to provide a luminescence assisting material for producing an organic electroluminescent device having characteristics such as a low driving voltage, high luminous efficiency, and / or long service life.

[0006] To achieve the above object, the present invention adopts the following technical solutions:

[0007] A luminescence assisting material, the general structural formula of which is shown in Chemical Formula 1:

[0008]

[0009] Wherein, X is selected from oxygen or sulfur;

[0010] R is selected from one of hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, sulfonic acid group, phosphoric acid group, boranyl, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted 3- to 30-membered heteroaryl, wherein the heteroatom is N, O, S, Si, P or Se.

[0011] Ar is selected from substituted or unsubstituted C6-C30 aryl, Ar is fused to the benzene ring, and Ar can be fused to the benzene ring at the 1,2-position or 2,3-position or 3,4-position;

[0012] Ar1 and Ar2 are each independently selected from substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted 3- to 30-membered heterocycloalkyl, wherein the heteroatom is N, O, S, Si, P or Se, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3- to 20-membered heteroaryl, wherein the heteroatom is N, O, S, Si, P or Se, substituted or unsubstituted C10-C30 fused ring group, and substituted or unsubstituted C5-C30 spiro ring group, one or more of them;

[0013] L is selected from substituted or unsubstituted C6-C20 aryl.

[0014] Further, the R is selected from one of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C5 alkyl, substituted or unsubstituted C6-C10 aryl, and substituted or unsubstituted 3- to 10-membered heteroaryl.

[0015] Still further, the R is selected from one of methyl, ethyl, isopropyl, tert-butyl, phenyl, biphenyl, naphthyl, terphenyl, and pyridyl.

[0016] Even further, the R is selected from methyl or phenyl.

[0017] Further, the Ar1 and Ar2 are each independently selected from substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted 3- to 20-membered heterocycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted 3- to 18-membered heteroaryl, substituted or unsubstituted C10-C25 fused ring group, and substituted or unsubstituted C5-C20 spiro ring group, one or more of them.

[0018] Still further, the Ar1 and Ar2 are each independently selected from any of the following groups or a combination thereof:

[0019]

[0020] Even further, the Ar1 and Ar2 are independently selected from any of the following groups or a combination thereof:

[0021]

[0022]

[0023] Furthermore, Ar1 and Ar2 are independently selected from any of the following groups or combinations thereof:

[0024]

[0025] Further, L is selected from the following general formula:

[0026]

[0027] Still further, L is selected from the following general formula:

[0028]

[0029] Further, the general formula of the above luminescence assisting material structure is as follows:

[0030] In the above formulas 1-1 to 1-10, R, Ar, Ar1, Ar2, and X are defined as above. Still further, the general formula of the above luminescence assisting material structure is as follows:

[0031]

[0032] Still further, the above luminescence assisting material is any one of the following structures, but not limited thereto:

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041] In the above terms of the present invention, "substituted" means that a hydrogen atom bonded to a carbon atom of a compound becomes another substituent, and there is no limitation on the substitution position as long as the position is where the hydrogen atom is substituted (i.e., the position where the substituent can substitute), and when two or more substituents are substituted, the two or more substituents can be the same or different from each other. A 3- to 10-membered heteroaryl group, wherein the heteroatoms in the heteroaryl group are selected from one or more of N, S, O, Si, P or Se, C1-C10 alkoxy groups, and C6-C20 arylamino groups.

[0042] Another object of the present invention is to provide a preparation method of the above-mentioned luminescence auxiliary material, and the synthesis route is as follows:

[0043]

[0044] Wherein R, X, Ar1, Ar2, L are defined as in the above chemical formula 1. Hal1 and Hal2 are selected from fluorine, chlorine, bromine or iodine;

[0045] The specific preparation method is as follows:

[0046] Step 1: Preparation of intermediate 1:

[0047] Under nitrogen protection, dissolve raw material A and raw material B in a mixed solution of toluene, ethanol and water, then add a palladium catalyst and potassium carbonate, stir evenly, heat up and reflux to prepare intermediate 1;

[0048] Step 2: Preparation of chemical formula 1:

[0049] Under nitrogen protection, dissolve intermediate 1 and raw material C in a toluene solution, add a palladium catalyst, a phosphine ligand and sodium tert-butoxide, stir evenly, heat up and reflux to prepare chemical formula 1.

[0050] Furthermore, the above preparation method specifically includes:

[0051] Step 1: Under nitrogen protection, dissolve raw material A (1.0 eq) and raw material B (1.0 eq) in a mixed solution of toluene, ethanol and water, add potassium carbonate (2.00 eq) and tetrakis(triphenylphosphine)palladium (0.01 eq), stir evenly, heat up to 90 °C, reflux for 5 h, after the solution cools to room temperature, retain the organic phase, and then extract the aqueous phase with ethyl acetate; after combining the organic phases, dry with anhydrous magnesium sulfate, and use a rotary evaporator to remove the solvent to obtain a solid organic matter. Completely dissolve the solid organic matter with a small amount of dichloromethane, then slowly drop it into a petroleum ether solution, stir evenly, precipitate will form, filter by suction to obtain a solid, wash it successively with anhydrous ethanol and petroleum ether, and dry it to obtain intermediate 1;

[0052] Step 2:

[0053] Under nitrogen protection, the intermediate 1 (1.0 eq) and the raw material C (1.0 eq) were dissolved in a toluene solution, tri(dibenzylideneacetone)dipalladium (0.01 eq), tri-tert-butylphosphine (0.05 eq) and sodium tert-butoxide (2.0 eq) were added, stirred evenly, heated to 95°C, and refluxed for 5 hours; after the reaction was completed, the temperature was slightly lowered, diatomaceous earth was used for filtration to remove salt and catalyst, and the filtrate was cooled to room temperature and washed three times with water, the organic phase was retained, and then the aqueous phase was extracted with ethyl acetate; after the organic phases were combined, they were dried with anhydrous magnesium sulfate, and the solvent was removed with a rotary evaporator; the remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V=10:4) to obtain Chemical Formula 1.

[0054] Another object of the present invention is to provide an organic electroluminescent device containing a light-emitting auxiliary material, comprising: a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode;

[0055] The organic layer contains the above-mentioned light-emitting auxiliary material.

[0056] Furthermore, the organic layer includes at least one of a hole injection layer, a hole transport layer, a luminescence auxiliary layer, a luminescent layer, an electron transport layer, and an electron injection layer, and at least one of the above-mentioned luminescence auxiliary materials is contained in this organic layer.

[0057] That is, the organic layer may be formed of one compound represented by the above Chemical Formula I alone or a mixture of two or more compounds.

[0058] Furthermore, a single compound represented by the above Chemical Formula 1 or a mixture of two or more compounds may be included in the light-emitting auxiliary layer.

[0059] The organic electroluminescent device provided by the present invention can be applied to an organic light emitting device (OLED), an organic solar cell (OSC), an electronic paper (e-paper), an organic photoreceptor (OPC) or an organic thin film transistor (OTFT).

[0060] The present invention does not limit the preparation method of the organic electroluminescent device. It is preferred to use thin film evaporation, electron beam evaporation or physical vapor deposition methods to evaporate metals and conductive oxides and their alloys on a substrate to form an anode, and then form an organic layer and evaporate a cathode thereon to obtain an organic electroluminescent device.

[0061] It can be seen from the above technical solution that compared with the prior art, the present invention has the following beneficial effects:

[0062] The present invention provides an organic electroluminescent compound containing furan or thiophene and triarylamine functional groups. By introducing triarylamine functional groups, the hole transport efficiency is greatly improved. The amine unit has steric hindrance to prevent electron spillage. Moreover, by introducing a benzodibenzofuran or benzodibenzothiophene structure, the molecular symmetry is reduced, the number of conformational isomers of the molecule is increased, and a rigid planar structure is formed, so that the molecules are not easily crystallized or aggregated, and the yield of manufacturing an organic EL device is improved. In particular, the bridging π group between the two functional groups uses a substituted aryl group, which has better efficiency and a long service life. Therefore, the combination of the two enables the organic light-emitting compound of the present invention to improve the light-emitting efficiency, driving voltage, service life and other characteristics in an organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0063] In order to more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the following will briefly introduce the drawings required for the description of the embodiments or the prior art. Obviously, the drawings in the following description are only the embodiments of the present invention. For those of ordinary skill in the art, other drawings can be obtained according to the provided drawings without creative efforts.

[0064] Figure 1 1H NMR spectrum of the light-emitting auxiliary material prepared in Example 1 of the present invention;

[0065] Figure 2 1H NMR spectrum of the light-emitting auxiliary material prepared in Example 2 of the present invention;

[0066] Figure 3 1H NMR spectrum of the light-emitting auxiliary material prepared in Example 3 of the present invention;

[0067] Figure 4 1H NMR spectrum of the light-emitting auxiliary material prepared in Example 4 of the present invention. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0068] The following will clearly and completely describe the technical solutions in the embodiments of the present invention with reference to the drawings in the embodiments of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all of the embodiments. All other embodiments obtained by those of ordinary skill in the art based on the embodiments of the present invention without creative efforts belong to the scope of protection of the present invention.

[0069] Example 1

[0070]

[0071] Under nitrogen protection, raw material A-7 (20.00mmol) and raw material B-7 (CAS No: 915201-07-9) (20.00mmol) were dissolved in 100.00ml of a mixed solution of toluene, ethanol and water, potassium carbonate (40.00mmol), tetrakistriphenylphosphine palladium (0.20mmol) were added, stirred evenly, heated to 90°C, refluxed for 5h, and after the solution was cooled to room temperature, the organic phase was retained, and then the aqueous phase was extracted with ethyl acetate; after the organic phases were combined, they were dried with anhydrous magnesium sulfate, and the solvent was removed with a rotary evaporator to obtain solid organic matter. A small amount of dichloromethane was used to completely dissolve the solid organic matter, and then it was slowly added dropwise to the petroleum ether solution, stirred evenly, and a precipitate was precipitated. The solid was filtered to obtain the solid, and it was rinsed with anhydrous ethanol and petroleum ether in turn, and dried to obtain intermediate 1 (7.37g, yield: 84.77%);

[0072]

[0073] Under nitrogen protection, intermediate 1 (16.09 mmol) and raw material C-7 (CAS No: 102113-98-4) (16.09 mmol) were dissolved in 110.00 ml toluene solution, tri(dibenzylideneacetone)dipalladium (0.16 mmol), tri-tert-butylphosphine (0.80 mmol) and sodium tert-butoxide (32.18 mmol) were added, stirred evenly, heated to 95 ° C, and refluxed for 5 h; after the reaction was completed, the temperature was slightly lowered, diatomaceous earth was used for filtration to remove salt and catalyst, the filtrate was cooled to room temperature, washed three times with water, the organic phase was retained, and then the aqueous phase was extracted with ethyl acetate; after the organic phases were combined, they were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V = 10:4) to obtain compound-7 (9.14 g, yield: 78.89%, Mw: 719.88).

[0074] The obtained compound-7 was tested and analyzed, and the results were as follows:

[0075] HPLC purity: >99.95%.

[0076] Mass spectrometry test: theoretical value is 719.88; tested value is 719.57.

[0077] Elemental Analysis:

[0078] Calculated values: C, 88.43; H, 5.18; N, 1.95; O, 4.44.

[0079] The test values ​​are: C, 88.08; H, 5.45; N, 2.23; O, 4.10.

[0080] H NMR spectrum: Figure 1 shown.

[0081] Example 2

[0082]

[0083] Under nitrogen protection, raw material A-45 (CAS No: 1846601-97-5) (20.00mmol) and raw material B-45 (20.00mmol) were dissolved in 100.00ml of a mixed solution of toluene, ethanol and water, potassium carbonate (40.00mmol) and tetrakistriphenylphosphine palladium (0.20mmol) were added, stirred evenly, heated to 90°C, and refluxed for 5h; after the solution was cooled to room temperature, the organic phase was retained, and then the aqueous phase was extracted with ethyl acetate; after the organic phases were combined, they were dried with anhydrous magnesium sulfate, and the solvent was removed with a rotary evaporator to obtain solid organic matter. A small amount of dichloromethane was used to completely dissolve the solid organic matter, and then it was slowly added dropwise to the petroleum ether solution, stirred evenly, and a precipitate was precipitated. The solid was filtered to obtain the solid, and it was rinsed with anhydrous ethanol and petroleum ether in turn, and dried to obtain intermediate 1 (6.08g, yield: 84.69%);

[0084]

[0085] Under nitrogen protection, intermediate 1 (16.72 mmol) and raw material C-45 (CAS No:1918982-76-9) (16.72mmol) was dissolved in 130.00ml toluene solution, tri(dibenzylideneacetone)dipalladium (0.17mmol), tri-tert-butylphosphine (0.84mmol) and sodium tert-butoxide (33.44mmol) were added, stirred evenly, heated to 95°C, and refluxed for 5h; after the reaction was completed, the temperature was slightly lowered, filtered using diatomaceous earth to remove salt and catalyst, the filtrate was cooled to room temperature, washed three times with water, the organic phase was retained, and then the aqueous phase was extracted with ethyl acetate; after the organic phases were combined, they were dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V=10:4) to obtain compound-45 (9.51g, yield: 76.42%, Mw: 743.91).

[0086] The obtained compound-45 was tested and analyzed, and the results were as follows:

[0087] HPLC purity: >99.96%.

[0088] Mass spectrometry test: theoretical value is 743.91; tested value is 743.59.

[0089] Elemental Analysis:

[0090] Calculated values: C, 88.80; H, 5.01; N, 1.88; O, 4.30.

[0091] The test values ​​are: C, 88.47; H, 5.38; N, 1.72; O, 4.65.

[0092] H NMR spectrum: Figure 2 shown.

[0093] Example 3

[0094]

[0095] Under nitrogen protection, raw material A-89 (20.00mmol) and raw material B-89 (20.00mmol) were dissolved in a mixed solution of 120.00ml toluene, ethanol and water, potassium carbonate (40.00mmol) and tetrakistriphenylphosphine palladium (0.20mmol) were added, stirred evenly, heated to 90°C, and refluxed for 5h; after the solution was cooled to room temperature, the organic phase was retained, and then the aqueous phase was extracted with ethyl acetate; after the organic phases were combined, they were dried with anhydrous magnesium sulfate, and the solvent was removed with a rotary evaporator to obtain solid organic matter. A small amount of dichloromethane was used to completely dissolve the solid organic matter, and then it was slowly added dropwise to the petroleum ether solution, stirred evenly, and a precipitate was precipitated. The solid was filtered to obtain the solid, and it was rinsed with anhydrous ethanol and petroleum ether in turn, and dried to obtain intermediate 1 (8.45g, yield: 82.64%);

[0096]

[0097] Under nitrogen protection, intermediate 1 (15.65 mmol) and raw material C-89 (CAS No:897671-74-8) (15.65mmol) was dissolved in 130.00ml toluene solution, tri(dibenzylideneacetone)dipalladium (0.16mmol), tri-tert-butylphosphine (0.78mmol) and sodium tert-butoxide (31.30mmol) were added, stirred evenly, heated to 95°C, and refluxed for 5h; after the reaction was completed, the temperature was slightly lowered, filtered using diatomaceous earth to remove salt and catalyst, the filtrate was cooled to room temperature, washed three times with water, the organic phase was retained, and then the aqueous phase was extracted with ethyl acetate; after the organic phases were combined, they were dried using anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator; the remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V=10:4) to obtain compound-89 (10.51g, yield: 74.95%, Mw: 896.10).

[0098] The obtained compound-89 was tested and analyzed, and the results were as follows:

[0099] HPLC purity: >99.95%.

[0100] Mass spectrometry test: The theoretical value is 896.10; the measured value is 895.84.

[0101] Elemental analysis:

[0102] Calculated values are: C, 89.80; H, 5.06; N, 1.56; O, 3.57.

[0103] Measured values are: C, 89.52; H, 5.37; N, 1.88; O, 4.02.

[0104] 1H NMR: As Figure 3 shown.

[0105] Example 4

[0106]

[0107] Under nitrogen protection, raw material A-119 (20.00 mmol) and raw material B-119 (CAS No: 897671-74-8) (20.00 mmol) were dissolved in a mixed solution of 120.00 ml of toluene, ethanol and water. Potassium carbonate (40.00 mmol) and tetrakis(triphenylphosphine)palladium (0.20 mmol) were added, and the mixture was stirred evenly. The temperature was raised to 90 °C and refluxed for 5 h. After the solution was cooled to room temperature, the organic phase was retained, and then the aqueous phase was extracted with ethyl acetate. After combining the organic phases, it was dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic matter. A small amount of dichloromethane was used to completely dissolve the solid organic matter, and then it was slowly added dropwise to a petroleum ether solution and stirred evenly. A precipitate was formed, and the solid was obtained by filtration. It was washed successively with anhydrous ethanol and petroleum ether and dried to obtain Intermediate 1 (7.18 g, yield: 82.58%);

[0108]

[0109] Under nitrogen protection, intermediate 1 (17.29 mmol) and raw material C-119 (CAS No:2667572-85-0) (17.29mmol) was dissolved in 120.00ml toluene solution, tri(dibenzylideneacetone)dipalladium (0.17mmol), tri-tert-butylphosphine (0.86mmol) and sodium tert-butoxide (34.58mmol) were added, stirred evenly, heated to 95°C, and refluxed for 5h; after the reaction was completed, the temperature was slightly lowered, diatomaceous earth was used for filtration to remove salt and catalyst, the filtrate was cooled to room temperature, washed three times with water, the organic phase was retained, and then the aqueous phase was extracted with ethyl acetate; after the organic phases were combined, they were dried with anhydrous magnesium sulfate, and the solvent was removed with a rotary evaporator; the remaining substance was purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V=10:4) to obtain compound-119 (11.11g, yield: 73.87%, Mw: 870.06).

[0110] The obtained compound-119 was tested and analyzed, and the results were as follows:

[0111] HPLC purity: >99.97%.

[0112] Mass spectrometry test: theoretical value is 870.06; tested value is 869.87.

[0113] Elemental Analysis:

[0114] Calculated values: C, 89.73; H, 4.98; N, 1.61; O, 3.68.

[0115] The test values ​​are: C, 89.48; H, 5.18; N, 1.52; O, 4.03.

[0116] H NMR spectrum: Figure 4 shown.

[0117] Since the general structural formula is Formula 1 in the content of the invention, the synthesis routes and principles of other compounds are the same as those of the above-mentioned embodiments, so they are not listed here. Among them, Examples 5 to 35 of the present invention can obtain the luminescent auxiliary materials shown in Table 1 according to the above preparation method:

[0118] Table 1:

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127] For the organic electroluminescent device prepared by using the luminescence assisting material provided in the above embodiment, when the organic layer includes a luminescence assisting layer, the luminescence assisting layer includes the luminescence assisting material provided in the above embodiment.

[0128] Device Example 1

[0129] The structure of the prepared OLED device is: ITO anode / HIL / HTL / EML / ETL / EIL / cathode / light extraction layer

[0130] a. ITO anode: The ITO (indium tin oxide)-Ag-ITO (indium tin oxide) glass substrate with a coating thickness of was cleaned twice in distilled water, ultrasonically washed for 30 min, then repeatedly cleaned twice with distilled water, ultrasonically washed for 10 min. After the washing, it was ultrasonically washed with methanol, acetone, and isopropanol in sequence (each washing for 5 min), dried, then transferred to a plasma cleaner for washing for 5 min, and then sent to an evaporation coater. Using this substrate as the anode, other functional layers were evaporated thereon in sequence.

[0131] b. HIL (hole injection layer): At a deposition rate of , the hole injection layer materials HT-1 and P-dopant were vacuum deposited. Their chemical formulas are shown as follows. The deposition rate ratio of HT-1 and P-dopant is 97:3, and the thickness is 10 nm;

[0132] c. HTL (hole transport layer): At a deposition rate of , 130 nm of HT-1 was vacuum deposited on the hole injection layer as the hole transport layer;

[0133] d. Luminescence assisting layer: At a deposition rate of , 10 nm of Compound 7 provided in the above embodiment was vacuum deposited on the hole transport layer as the luminescence assisting layer;

[0134] e. EML (emitting layer): Then, on the above luminescence assisting layer, at a deposition rate of , a main material (Host) and a doping material (Dopant) with a thickness of 20 nm were vacuum deposited as the emitting layer. Their chemical formulas of Host and Dopant are shown as follows. The deposition rate ratio of Host and Dopant is 98:2.

[0135] f. ETL (Electron Transport Layer): At a deposition rate, vacuum deposit ET-1 and Liq with a thickness of 35 nm as the electron transport layer. The chemical formula of ET-1 is shown below. The deposition rate ratio of ET-1 and Liq is 50:50.

[0136] g. EIL (Electron Injection Layer): At a deposition rate, deposit a 1.0 nm Yb film layer to form the electron injection layer.

[0137] h. Cathode: At a deposition rate ratio, deposit 18 nm of magnesium and silver. The deposition rate ratio is 1:9 to obtain the OLED device.

[0138] i. Light Extraction Layer: At a deposition rate, vacuum deposit CPL-1 with a thickness of 70 nm on the cathode as the light extraction layer. Subsequently, encapsulate the deposited substrate. First, use a gluing device to coat the cleaned cover plate with UV glue, then move the coated cover plate to the lamination section, place the deposited substrate on top of the cover plate, and finally laminate the substrate and the cover plate under the action of a laminating device, while simultaneously completing the light curing of the UV glue.

[0139]

[0140] Referring to the method provided in Device Example 1 above, respectively select Compounds 13, 16, 21, 29, 37, 42, 45, 56, 57, 59, 60, 75, 81, 89, 97, 99, 108, 110, 113, 119, 124, 125, 127, 133, 146, 150, 154, 168, 171, 181, 187, 193, 201, 208 to replace Compound 7 for the deposition of the light-emitting auxiliary layer, and prepare the corresponding organic electroluminescent devices, which are respectively denoted as Device Examples 2 to 35.

[0141] Device Comparative Example 1:

[0142] This comparative example provides an organic electroluminescent device. The only difference between the preparation method of this organic electroluminescent device and that of Device Example 1 is that this organic electroluminescent device respectively uses existing comparative compounds a, b, c, d, e, f to replace the light-emitting auxiliary material (Compound 7) in the above Device Example 1 for deposition to prepare Device Comparative Examples 1 to 6. Among them, the chemical structural formulas of comparative compounds a, b, c, d, e, f are:

[0143]

[0144] The driving voltage, luminous efficiency, BI value, and lifespan of the organic electroluminescent devices obtained from Device Examples 1 to 35 and Device Comparative Examples 1 to 6 of the above devices were characterized at a brightness of 1000 (nits), and the test results are shown in Table 2 below:

[0145] Table 2:

[0146]

[0147]

[0148]

[0149]

[0150]

[0151] As can be seen from Table 2, compared with the existing organic electroluminescent devices provided in Comparative Examples 1 to 6, the organic electroluminescent devices prepared using the luminescence assisting material provided by the present invention have significantly reduced driving voltage, and significantly improved luminous efficiency, BI, and lifespan.

[0152] In this specification, each embodiment is described in a progressive manner. The key point of each embodiment is to illustrate the differences from other embodiments. For the same or similar parts among the embodiments, reference can be made to each other. For the devices disclosed in the embodiments, since they correspond to the methods disclosed in the embodiments, the description is relatively simple, and reference can be made to the description in the method part for relevant parts.

[0153] The above description of the disclosed embodiments enables those skilled in the art to implement or use the present invention. Various modifications to these embodiments will be obvious to those skilled in the art. The general principles defined herein can 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 will be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. A luminescence auxiliary material, characterized in that, The luminescence assisting material is selected from the following structures:

2. An organic electroluminescent device containing a luminescence auxiliary material, characterized in that, Comprising: A first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode; The organic layer contains the luminescence assisting material described in claim 1.

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