An organic electroluminescence compound of a benzanthracene derivative, and a preparation method and application thereof

Abstract

The application discloses an organic electroluminescent compound of a benzanthracene derivative, a structural general formula of the organic electroluminescent compound of the benzanthracene derivative is shown in chemical formula 1: X is a chemical bond, O, S, Si(R4R5), C(R6R7) or NR8; Ar1, Ar2, R1-R3 are each independently selected from hydrogen, substituted or non-substituted C1-C10 alkyl, substituted or non-substituted C6-C30 aryl, substituted or non-substituted 3-30-membered heteroaryl, substituted or non-substituted C10-C30 condensed ring group, substituted or non-substituted C1-C30 alkoxy, substituted or non-substituted C1-C30 alkylmercapto, substituted or non-substituted C6-C30 arylamino, and substituted or non-substituted C6-C30 aryloxy. The organic electroluminescent compound has a short synthesis route, simple process, easily available raw materials, low cost and is suitable for industrial production.

Description

Technical Field

[0001] This invention relates to the field of luminescent materials technology, specifically to an organic electroluminescent compound of benzene anthracene derivative, its preparation method, and its application. Background Technology

[0002] Organic electrical components that utilize organic light-emitting phenomena typically have an anode, a cathode, and an organic layer between them. To improve the efficiency and stability of the organic electrical components, the organic layer is generally formed as a multilayer structure composed of various materials; for example, it can be formed from a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

[0003] Hole transport materials typically have low Most Occupied Molecular Orbitals (HOMO) values, which tend to reduce efficiency when materials with fast hole mobility are used to lower the driving voltage. In OLEDs, because hole mobility is faster than electron mobility, charge imbalance occurs in the emissive layer, leading to reduced efficiency and lifetime. Introducing an emissive auxiliary layer between the emissive and hole transport layers can effectively avoid these technical problems.

[0004] However, the materials currently available for the light-emitting auxiliary layer are limited. Most red light-emitting auxiliary layers used in panel production lines employ materials from Tokuyama and DowDuPont. These materials typically utilize fluorene ring structures, and the light-emitting auxiliary layer is formed from materials capable of addressing the hole transport layer problem, possessing suitable hole mobility to provide appropriate driving current. However, simply focusing on the core structural features of the light-emitting auxiliary layer material is insufficient to meet these requirements.

[0005] Therefore, providing a light-emitting auxiliary layer material with high T1 energy and wide bandgap to improve the efficiency and lifespan of organic electronic components is a technical problem that urgently needs to be solved by those skilled in the art. Summary of the Invention

[0006] In view of this, the present invention provides a light-emitting auxiliary layer material with superior performance by using a benzene anthracene derivative as the core and connecting different active sites thereon with side chains, which can solve the technical problem of unsatisfactory luminescence efficiency and lifetime of existing organic electroluminescent devices.

[0007] To achieve the above objectives, the present invention adopts the following technical solution: An organoluminescent compound of a benzene-anthracene derivative, the general structural formula of which is shown in Chemical Formula 1: ; Wherein, X is a chemical bond, or X is selected from O, S, Si (R4R5), C (R6R7) or NR8; Each of R1-R3 is independently selected from: hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3- to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring group, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C1-C30 alkathiol, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C6-C30 aryloxy; Each of R1-R3 is preferably selected independently from methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, alkoxy, aryloxy, phenyl, biphenyl, or naphthyl; the substituents R1-R3 are located at any position on the benzene ring, the number of R1 is 0-4, and the number of R2 and R3 is 0-3.

[0008] R4-R8 are each independently selected from: substituted or unsubstituted C1-C10 alkyl, C3-C15 cycloalkanes, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3- to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused cycloalkanes, and substituted or unsubstituted C1-C30 alkoxy groups. R4-R8 are each independently selected from methyl, ethyl, naphthyl, adamantyl, biphenyl, phenyl, heteroaryl, etc. The Ar1 and Ar2 are independently selected from: substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3- to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring group, substituted or unsubstituted C5-C30 spiro ring group, or Ar1 and Ar2 are each independently connected with adjacent substituents to form a monocyclic or polycyclic ring; Ar1 and Ar2 are each preferably naphthyl, phenanthryl, phenyl, methylphenyl, fluorenyl, dimethylphenyl, dimethylfluorenyl, terphenyl, biphenyl, dibenzofuran, dibenzothiophene and their derivatives.

[0009] Furthermore, the monocyclic or polycyclic ring is a C3-C30 aliphatic ring or a C6-C30 aromatic ring; at least one carbon atom in the aliphatic or aromatic ring is replaced by nitrogen, oxygen, sulfur or silicon.

[0010] The further beneficial effect of the above-mentioned method is that the performance modification of the benzene-anthracene core by the above-mentioned groups defined in this invention helps to improve the performance of the device.

[0011] The L is a linking bond, or L is selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted 3- to 30-membered heteroaryl, substituted or unsubstituted C10-C30 fused ring group, or substituted or unsubstituted C5-C30 spiro ring group.

[0012] In the above technical solutions, the term "substituted or unsubstituted" means substituted by one, two or more substituents selected from the following: deuterium; halogen group; nitrile group; hydroxyl group; carbonyl group; ester group; silyl group; boron group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkoxy group; substituted or unsubstituted alkenyl group; substituted or unsubstituted alkylamino group; substituted or unsubstituted heterocyclic amino group; substituted or unsubstituted arylamino group; substituted or unsubstituted aryl group; and substituted or unsubstituted heterocyclic group, or substituted by substituents connected to two or more substituents shown above, or without substituents. For example, "substituents connected to two or more substituents" can include biphenyl. In other words, biphenyl can be aryl, or can be interpreted as substituents connected to two phenyl groups.

[0013] In the above technical solutions, the preferred organic electroluminescent compound is selected from any one of the following structures: .

[0014] This invention also provides a method for preparing the above-mentioned organoelectroluminescent compounds of benzenexanthracene derivatives. in: The synthetic route when L is a substituent is as follows: ; The steps are as follows: (1) Dissolve reactant A and reactant B in a reaction vessel containing dry toluene. Add Pd2(dba)3, P(t-Bu)3, and t-BuONa to the reaction vessel under a nitrogen atmosphere, and heat to 110°C. React for 10 hours under stirring. After the reaction is completed, filter the filtrate with diatomaceous earth while it is hot to remove the salt and catalyst. Then cool the filtrate to room temperature and wash it with distilled water. Separate the washing liquid and retain the organic phase. Extract the aqueous phase with ethyl acetate. Combine the organic phase and the ethyl acetate extract phase. Dry the combined organic phase with magnesium sulfate and then remove the solvent by a rotary evaporator. Then purify the remaining substances by column chromatography to obtain intermediate C. (2) Under a nitrogen atmosphere, intermediate C, reactant D, tetra(triphenylphosphine)palladium and potassium carbonate were added to a mixed solvent of toluene, ethanol and water, respectively. The mixture was heated to 100°C and refluxed for 8 hours. After the reaction was completed, the mixture was cooled to room temperature. After the solid precipitated, the reaction solution was filtered and washed with water to remove the salt. Then, the solution was washed with ethanol to obtain a filter cake. The filter cake was dried and then recrystallized in 1,4-dioxane to obtain the compound shown in general formula I. or, When L is the linker bond, the synthesis route is: ; The steps are as follows: (1) Dissolve reactant a and reactant b in a reaction vessel containing dry toluene. Add Pd2(dba)3, P(t-Bu)3, and t-BuONa to the reaction vessel under a nitrogen atmosphere, heat to 110°C, and stir the mixture for 10 h. After the reaction is completed, filter the mixture with diatomaceous earth while it is hot to remove the salt and catalyst. Then cool the filtrate to room temperature and wash the filtrate with distilled water. After separating the washing liquid, retain the organic phase and extract the aqueous phase with ethyl acetate. Combine the organic phase and the ethyl acetate extract phase, dry the combined organic phase with magnesium sulfate, and remove the solvent by rotary evaporator. Then purify the remaining substances by column chromatography to obtain the compound shown in general formula I.

[0015] Furthermore, when L is a substituent, the molar ratio of reactant A to reactant B is 1:1.1; The intermediate C, reactant D, tetrakis(triphenylphosphine)palladium, and potassium carbonate are in a molar ratio of 1:1.1:0.01:2.4. When L is a chemical bond, the molar ratio of reactant a to reactant b is 1:1.1.

[0016] Furthermore, when L is a substituent or a chemical bond, the molar ratio of reactant a to P(t-Bu)3 and t-BuONa is 1:0.01-0.02:0.056:3; The preferred molar ratio of reactant a to P(t-Bu)3 and t-BuONa is 1:0.0112:0.056:3; The further beneficial effects of the above-mentioned method are that the reaction yields fewer by-products, faster reaction speed, and easier purification when the ratio specified in this invention is used.

[0017] Furthermore, when L is a substituent or chemical bond, the eluent for the column chromatography purification is dichloromethane and petroleum ether; the volume ratio of dichloromethane to petroleum ether is 1:9.

[0018] The further beneficial effect of the above-mentioned method is that, under the eluent ratio specified in this invention, it is possible to separate impurities from the product and obtain a substance with high purity.

[0019] The beneficial effects of this invention are as follows: the synthetic route of the organic electroluminescent compound of this invention is relatively short, the process is simple, the raw materials are readily available, the cost is low, and it is suitable for industrial production.

[0020] The present invention also provides the application of the above-mentioned benzene-anthracene derivative organic electroluminescent compounds in the preparation of organic electroluminescent devices.

[0021] An organic electroluminescent device comprises, in sequence, a first electrode, a plurality of organic layers and a second electrode; at least one of the organic layers is an organic electroluminescent compound of the aforementioned benzene-anthracene derivative.

[0022] Furthermore, the aforementioned organic layer includes one or more layers of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a hole injection-hole transport functional layer, a light-emitting layer, an electron transport layer, and an electron injection layer, and at least one layer contains the aforementioned organic electroluminescent compound; preferably, at least one layer of the organic layer contains a hole injection substance, a hole transport substance, a light-emitting auxiliary substance, or both a hole injection-hole transport functional layer.

[0023] When the organic layer is a single-layer structure, the organic layer is a light-emitting layer; when the organic layer is a multi-layer structure, the organic layer includes a light-emitting layer. The further beneficial effect of adopting the above is that the combination of different functional layers in this invention makes the energy level combination more reasonable.

[0024] Furthermore, the light-emitting layer comprises one or more of the following: a phosphorescent host, a fluorescent host, a phosphorescent dopant, and a fluorescent dopant. When the organic layer includes a hole transport layer or a light-emitting auxiliary layer, the hole transport layer comprises an organic light-emitting compound represented by Formula 1.

[0025] The further beneficial effects of the above-mentioned method are as follows: the use of the light-emitting auxiliary layer as defined in this invention makes the energy level transition between the hole transport layer and the light-emitting layer smoother, effectively reduces the potential barrier, reduces the driving voltage, extends the lifetime, and improves the luminous efficiency.

[0026] Compared with the prior art, the beneficial effects of the present invention are: the organic electroluminescent device provided by the present invention has high luminous efficiency, low driving voltage and long life. Detailed Implementation

[0027] The technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the scope of protection of the present invention.

[0028] Example 1: Preparation of Compound 9

[0029] Reactants A-9 (50 mmol) and B-9 (55 mmol) were dissolved in 200 mL of toluene in a reaction vessel. Then, under a nitrogen atmosphere, Pd₂(dba)₃ (0.56 mmol), P(t-Bu)₃ (2.8 mmol), and t-BuONa (150 mmol) were added. After addition, the reaction temperature was slowly increased to 110 °C, and the mixture was stirred for 10 h. The mixture was filtered hot using diatomaceous earth to remove salts and catalyst. After cooling the filtrate to room temperature, distilled water was added to wash the filtrate. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were then dried with magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using dichloromethane:petroleum ether at a volume ratio of 1:9 as the eluent to obtain final product 9 (21.7 g, yield 78%, MS: 557.27).

[0030] Example 2: Preparation of compound 23

[0031] Step 1: In a reaction vessel, reactants A-23 (50 mmol) and B-23 (55 mmol) were dissolved in 200 mL of toluene. Then, under a nitrogen atmosphere, Pd2(dba)3 (0.56 mmol), P(t-Bu)3 (2.8 mmol), and t-BuONa (150 mmol) were added. After addition, the reaction temperature was slowly increased to 110 °C, and the mixture was stirred for 10 h. The mixture was filtered hot using diatomaceous earth to remove salts and catalyst. After cooling the filtrate to room temperature, distilled water was added to wash the filtrate. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were then dried with magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using dichloromethane:petroleum ether at a volume ratio of 9:1 as the eluent to obtain intermediate C-23 (27.2 g, 75% yield).

[0032] Step 2: Under N2 protection, intermediates C-23 (35 mmol), D-23 (38.5 mmol), tetrakis(triphenylphosphine)palladium (0.35 mmol), and potassium carbonate (84 mmol) were added to a mixed solvent of 150 mL toluene, 50 mL ethanol, and 50 mL water, respectively. The mixture was refluxed for 8 h. After the reaction was completed, the mixture was cooled to room temperature. After the solid precipitated completely, it was filtered, washed with water to remove the salt, and then rinsed with a small amount of ethanol. The filter cake was dried and recrystallized from 1,4-dioxane (150 mL) to give the final product 23 (23.0 g, yield 82%, MS: 800.38).

[0033] Example 3: Preparation of Compound 44

[0034] Step 1: In a reaction vessel, reactants A-44 (50 mmol) and B-44 (55 mmol) were dissolved in 200 mL of toluene. Then, under a nitrogen atmosphere, Pd₂(dba)₃ (0.56 mmol), P(t-Bu)₃ (2.8 mmol), and t-BuONa (150 mmol) were added. After addition, the reaction temperature was slowly increased to 110 °C, and the mixture was stirred for 10 h. The mixture was filtered hot using diatomaceous earth to remove salts and catalyst. After cooling the filtrate to room temperature, distilled water was added to wash the filtrate. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were then dried with magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using dichloromethane:petroleum ether at a volume ratio of 1:9 to obtain intermediate C-44 (22.0 g, 77% yield).

[0035] Step 2: Under N2 protection, intermediates C-44 (35 mmol), D-44 (38.5 mmol), tetrakis(triphenylphosphine)palladium (0.35 mmol), and potassium carbonate (84 mmol) were added to a mixed solvent of 150 mL toluene, 50 mL ethanol, and 50 mL water, respectively. The mixture was refluxed for 8 h. After the reaction was completed, the mixture was cooled to room temperature. After the solid precipitated completely, it was filtered, washed with water to remove the salt, and then rinsed with a small amount of ethanol. The filter cake was dried and recrystallized in 1,4-dioxane (150 mL) to give the final product 44 (25.3 g, yield 81%, MS: 894.40).

[0036] Example 4: Preparation of Compound 100

[0037] Step 1: In a reaction vessel, reactants A-100 (50 mmol) and B-100 (55 mmol) were dissolved in 200 mL of toluene. Then, under a nitrogen atmosphere, Pd₂(dba)₃ (0.56 mmol), P(t-Bu)₃ (2.8 mmol), and t-BuONa (150 mmol) were added. The reaction temperature was slowly increased to 110 °C, and the mixture was stirred for 10 h. The mixture was filtered hot using diatomaceous earth to remove salts and catalyst. After cooling the filtrate to room temperature, distilled water was added to wash the filtrate. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were then dried with magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using dichloromethane:petroleum ether at a volume ratio of 1:9 to obtain intermediate C-100 (23.4 g, yield 73%).

[0038] Step 2: Under N2 protection, intermediates C-100 (35 mmol), D-100 (38.5 mmol), tetrakis(triphenylphosphine)palladium (0.35 mmol), and potassium carbonate (84 mmol) were added to a mixed solvent of 150 mL toluene, 50 mL ethanol, and 50 mL water, respectively. The mixture was refluxed for 8 h. After the reaction was completed, the mixture was cooled to room temperature. After the solid precipitated completely, it was filtered, washed with water to remove the salt, and then rinsed with a small amount of ethanol. The filter cake was dried and recrystallized in 1,4-dioxane (150 mL) to give the final product 100 (26.9 g, yield 85%, MS: 904.21).

[0039] Example 5: Preparation of Compound 116

[0040] Step 1: In a reaction vessel, reactants A-116 (50 mmol) and B-116 (55 mmol) were dissolved in 200 mL of toluene. Then, under a nitrogen atmosphere, Pd₂(dba)₃ (0.56 mmol), P(t-Bu)₃ (2.8 mmol), and t-BuONa (150 mmol) were added. After addition, the reaction temperature was slowly increased to 110 °C, and the mixture was stirred for 10 h. The mixture was filtered hot using diatomaceous earth to remove salts and catalyst. After cooling the filtrate to room temperature, distilled water was added to wash the filtrate. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were then dried with magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using dichloromethane:petroleum ether at a volume ratio of 1:9 as the eluent to obtain intermediate C-116 (22.1 g, 74% yield).

[0041] Step 2: Under N2 protection, intermediates C-116 (35 mmol), D-116 (38.5 mmol), tetrakis(triphenylphosphine)palladium (0.35 mmol), and potassium carbonate (84 mmol) were added to a mixed solvent of 150 mL toluene, 50 mL ethanol, and 50 mL water, respectively. The mixture was refluxed for 8 h. After the reaction was completed, the mixture was cooled to room temperature. After the solid precipitated completely, it was filtered, washed with water to remove the salt, and then rinsed with a small amount of ethanol. The filter cake was dried and recrystallized from 1,4-dioxane (150 mL) to give the final product 116 (25.5 g, yield 82%, MS: 888.21).

[0042] The synthesis methods for other compounds are the same as those listed in the examples above, so they will not be listed one by one here. Some mass spectra and molecular formulas are listed in Table 1 below.

[0043] Table 1:

[0044] [Device Example 1]: Fabrication of an organic electroluminescent device containing compound 9 An ITO glass substrate with a coating thickness of 1500 Å was washed twice with distilled water, ultrasonically cleaned for 30 minutes, repeatedly washed twice with distilled water, and ultrasonically cleaned for 10 minutes. After distilled water cleaning, it was ultrasonically cleaned in sequence with solvents such as isopropanol, acetone, and methanol, and then dried. The substrate was then transferred to a plasma cleaner and cleaned for 5 minutes before being sent to an evaporation machine. A 50 nm thick layer of compound NPB and F4-TCNQ (doping ratio 97:3) was deposited on the prepared ITO transparent electrode as a hole injection layer. Then, a 50 nm thick hole transport layer was vacuum-deposited on the formed hole injection layer using compound NPB. Finally, a 20 nm thick layer of compound 9 was deposited on the hole transport layer as a light-emitting auxiliary layer. Then, a 20 nm thick base material CBP and a dopant material (btfmp)2Ir (dbm) were deposited on the aforementioned light-emitting auxiliary layer. The weight ratio of the base material to the dopant material was 95:5. Next, a 10 nm thick BAlq layer was vacuum-deposited on the light-emitting layer as a hole-blocking layer, and a 40 nm thick Alq3 electron transport layer was deposited on the aforementioned light-emitting layer. On the aforementioned electron transport layer, a 0.5 nm thick lithium fluoride (LiF) layer was vacuum-deposited as an electron injection layer. Finally, a 150 nm thick aluminum layer was deposited as a cathode, thus completing the fabrication of the organic electroluminescent device.

[0045]

[0046] Organic electroluminescent devices containing compounds 10, 18, 21, 23, 25, 32, 38, 40, 44, 45, 51, 73, 78, 80, 85, 90, 95, 98, 100, 102, 111, 116, and 118 were fabricated using the same methods, respectively, in Examples 2 to 24.

[0047] [Device Comparison Example 1] - [Device Comparison Example 4] Comparative Example 1: Fabrication of an organic electroluminescent device containing comparative compound 1.

[0048] Following the method of Device Example 1, the compound 9 of the light-emitting auxiliary layer was replaced with the comparative compound 1, and other methods were the same to fabricate an organic electroluminescent device containing the comparative compound 1.

[0049] Comparative Example 2: Fabrication of an organic electroluminescent device containing comparative compound 2.

[0050] Following the method of Device Example 1, the compound 9 of the light-emitting auxiliary layer was replaced with the comparative compound 2, and other methods were the same to fabricate an organic electroluminescent device containing the comparative compound 2.

[0051] Comparative Example 3: Comparative Example 3 was fabricated according to the method of Comparative Example 1. The difference is that it does not contain a light-emitting auxiliary layer.

[0052] Comparative Example 4: Fabrication of an organic electroluminescent device containing comparative compound 3.

[0053] Following the method of Device Example 1, the compound 9 of the light-emitting auxiliary layer was replaced with the comparative compound 3, and other methods were the same to fabricate an organic electroluminescent device containing the comparative compound 2.

[0054]

[0055] Table 2 shows the test results of the luminous properties of the device in Examples 1-24 and Comparative Examples 1-4 of the present invention (luminance value 5000 cd / m²). 2 ).

[0056] Table 2:

[0057] As can be seen from Table 2, the organic electroluminescent devices prepared using the compounds provided in this invention as the light-emitting auxiliary layer material have significantly improved driving voltage, luminous efficiency, and lifetime compared with organic electroluminescent devices using comparative compounds 1-3 as the light-emitting auxiliary layer material and those without a light-emitting auxiliary layer.

[0058] Compared with Comparative Examples 1-2, the device embodiment shows a decrease in driving voltage of about 1.0V, an increase in luminous efficiency of about 7-13%, and an increase in device lifetime of 27-60h.

[0059] The difference between Comparative Example 4 and the compound of the present invention is that the side chain is connected on one side of the benzene ring. In terms of device performance, the driving voltage of the compound of the present invention is higher than that of Comparative Example 4, the luminous efficiency is comparable to that of Comparative Example 4, and the device life is greatly extended, up to 160 hours.

[0060] The reason why the device data obtained by the same parent core and the same device fabrication method are significantly different may be because the "L" connection position in the side chain structure is different, which changes the spatial structure of the compound.

[0061] Those skilled in the art will readily recognize that many modifications and variations can be made to the invention without departing from its spirit and scope. Therefore, it is contemplated that the invention covers the modifications and variations provided within the scope of the appended claims and their equivalents.

[0062] The above description of the disclosed embodiments enables those skilled in the art to make or use the invention. Various modifications to these embodiments will be readily apparent to those 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 invention. Therefore, the invention is not to be limited to the embodiments shown herein, but is accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. An organoelectroluminescent compound of a benzene-anthracene derivative, characterized in that, The organoelectroluminescent compound of the benzanthracene derivative has any of the following structures: 。 2. The application of an organic electroluminescent compound of the benzene anthracene derivative according to claim 1 in the preparation of organic electroluminescent devices.

3. An organic electroluminescent device, characterized in that, It comprises, in sequence, a first electrode, several organic layers, and a second electrode; at least one of the organic layers comprises an organic electroluminescent compound of the benzene anthracene derivative of claim 1.

4. The organic electroluminescent device according to claim 3, characterized in that, The organic layer comprises one or more layers of a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a hole injection-hole transport functional layer, a light-emitting layer, an electron transport layer, and an electron injection layer, and at least the light-emitting auxiliary layer comprises an organic electroluminescent compound of the benzene anthracene derivative of claim 1.

Images