Polycyclic aromatic compound, organic electroluminescent device, and optoelectronic apparatus

Abstract

The application belongs to the technical field of materials, and provides a polycyclic aromatic compound, an organic electroluminescent device and an optoelectronic device. The application introduces a double ring structure on the basis of a mother nucleus, provides a high conjugated electron distribution system of the polycyclic aromatic compound, effectively and orderly stacks the molecules, and thus plays the best carrier transmission and migration under a certain electric field. Meanwhile, some rigid and high steric hindrance molecular groups are synthesized in the molecular structure, the molecules combine long-range interaction and delocalization in a quite unique way, cause the effect of short-distance high radiation decay rate, and the reorganization of the electric charge density can maximally reduce the gap between the singlet state and the triplet state. The polycyclic conjugated rigid structure effectively inhibits the vibration of the molecular ground state and the excited state, reacts in a narrower emission band, and introduces groups such as tert-butyl and tert-amyl to improve the color purity. The service life and the luminous efficiency of the organic electroluminescent device prepared by using the application are obviously improved.

Description

Technical Field

[0001] This invention belongs to the field of materials technology, and particularly relates to a polycyclic aromatic compound, an organic electroluminescent device, and an optoelectronic device. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are gradually coming into view as a new and promising display technology. An OLED is an electroluminescent device formed by a multilayer organic thin-film structure.

[0003] Organic light-emitting diodes (OLEDs) are self-emissive devices that utilize the principle that fluorescent materials emit light by recombination of holes injected from the anode and electrons injected from the cathode when an electric field is applied. They have the following structure: an anode, a cathode, and an organic material layer between them. To improve the efficiency and stability of OLEDs, the organic material layer typically comprises multiple layers of different materials, such as a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer, an electron transport layer (ETL), and an electron injection layer (EIL). In such OLEDs, when a voltage is applied between the anode and cathode, holes from the anode and electrons from the cathode are injected into the organic material layer, and the resulting excitons migrate to the ground state, producing light with a specific wavelength.

[0004] The core organic light-emitting materials in OLED display technology achieve full color gamut through a mixture of red, green, and blue light-emitting materials. The development of novel light-emitting materials is the driving force behind the continuous advancement of electroluminescence technology and a research hotspot in the organic electroluminescence industry. The development of novel blue organic electroluminescent materials enables devices to achieve high luminous efficiency and better lifespan. Meanwhile, blue light-emitting materials with narrow half-width and high color purity are the focus of blue light-emitting material development.

[0005] Currently, the multiple vibrational effect (MR effect) is employed to utilize the opposite vibrations of boron and heteroatoms such as nitrogen and oxygen to construct polycyclic aromatic compounds formed by the condensation of multiple aromatic rings by boron atoms and heteroatoms such as nitrogen and oxygen. This results in the preparation of special rigid material systems containing boron atoms and nitrogen-oxygen heteroatoms. These fluorescent molecules exhibit high radiative transition rates, narrow full width at half maximum (FWHM), and high color purity, but their performance in terms of device lifetime and luminous efficiency is not particularly ideal. Moreover, the industrialization of this technology still faces many key challenges. Therefore, developing new materials remains a pressing issue for those skilled in the art. Summary of the Invention

[0006] The purpose of this invention is to provide a polycyclic aromatic compound that addresses the problems of unsatisfactory performance in device lifetime and luminous efficiency of existing organic light-emitting materials, which are also detrimental to industrialization.

[0007] This invention is achieved by providing a polycyclic aromatic compound, the structure of which is shown in general formula I:

[0008]

[0009] In general formula I, n0 is an integer from 0 to 3; R0 is one of deuterium, nitrile, halogen group, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C6-C30 heteroaryl.

[0010] Ar1 and Ar2 may be the same or different from each other, and are independently compounds represented by Formula 1, Formula 2 or Formula 3, respectively, and at least one of Ar1 and Ar2 is Formula 1;

[0011]

[0012] Ar3 and Ar4 may be the same as or different from each other, and are each one of the following compounds:

[0013]

[0014] Z is either C or N; where, when Z is C, n1 is an integer from 0 to 13; when Z is N, n1 is an integer from 0 to 12.

[0015] n2, n3, and n5 are either 0 or 1;

[0016] R1 is one of deuterium, nitrile, halogen group, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C6-C30 aryl, or substituted or unsubstituted C6-C30 heteroaryl.

[0017] R2-R5 are, independently, a deuterium, a nitrile, a halogen, a substituted or unsubstituted C1-C20 alkyl, a substituted or unsubstituted C1-C20 alkoxy, a substituted or unsubstituted C6-C30 aryl, or a substituted or unsubstituted C6-C30 heteroaryl.

[0018] Another object of the present invention is an organic electroluminescent device comprising the above-described polycyclic aromatic compounds.

[0019] Another object of the present invention is an optoelectronic device comprising the above-described organic electroluminescent device.

[0020] This invention provides a novel high-conjugation electron distribution system for polycyclic aromatic compounds by introducing a bicyclic structure into the core, allowing for efficient and orderly intermolecular stacking and thus optimal carrier transport and migration under a specific electric field. Simultaneously, the synthesis of rigid molecular groups with high steric hindrance in the molecular structure results in a unique combination of long-range interactions and delocalization, leading to a charge density reorganization with a high radiative attenuation rate over short distances, which minimizes the singlet-triplet gap. The multi-ring conjugated rigid structure effectively suppresses vibrations in both the ground and excited states, resulting in a narrower emission band. Furthermore, the introduction of tert-butyl and tert-amyl groups enhances color purity. In addition, the organic electroluminescent devices prepared using this invention exhibit significantly improved lifespan and luminous efficiency. Attached Figure Description

[0021] Figure 1 These are the proton NMR spectra of non-existing raw materials provided in Examples 1-2 of this invention;

[0022] Figure 2 These are the proton NMR spectra of non-existing raw materials provided in Examples 3-4 of this invention;

[0023] Figure 3 This is the 1H NMR spectrum of compound 3 provided in Example 1 of this invention;

[0024] Figure 4 This is the hydrogen nuclear magnetic resonance spectrum of compound 6 provided in Example 2 of this invention. Detailed Implementation

[0025] To make the objectives, technical solutions, and advantages of this invention clearer, the invention will be further described in detail below with reference to embodiments. It should be understood that the specific embodiments described herein are merely illustrative and not intended to limit the invention.

[0026] This invention provides a polycyclic aromatic compound with the following structural formula I:

[0027]

[0028] In general formula I, Ar1 and Ar2 may be the same or different from each other, and are independently selected from formula 1, formula 2, and formula 3, and at least one of Ar1 and Ar2 is formula 1.

[0029]

[0030] In Formula 1, Z is selected from C and N; R1 is selected from deuterium, nitrile, halogen group, substituted or unsubstituted C1-C20 alkyl; substituted or unsubstituted C1-C20 alkoxy; substituted or unsubstituted C6-C30 aryl; substituted or unsubstituted C6-C30 heteroaryl, wherein the heteroatom is selected from oxygen, nitrogen, and sulfur;

[0031] When Z is selected from C, n1 takes the value of an integer between 0 and 13;

[0032] When Z is selected from N, n1 takes the value of an integer between 0 and 12;

[0033] Formula 1 is preferably structured as follows: (In the preferred structure, the position of the parallel ring is the same as the position of the parallel ring in Formula 1)

[0034]

[0035] In equations 2 and 3, n2-n3 is selected from 0 or 1, and not both of them are 0;

[0036] R2-R4 are each independently selected from deuterium, nitrile, halogen group, substituted or unsubstituted C1-C20 alkyl; substituted or unsubstituted C1-C20 alkoxy; substituted or unsubstituted C6-C30 aryl; substituted or unsubstituted C6-C30 heteroaryl, wherein the heteroatom is selected from oxygen, nitrogen, and sulfur.

[0037] Furthermore, R2-R4 are preferably configured as follows:

[0038]

[0039] In general formula I, n0 is an integer from 0 to 3, and R0 is selected from deuterium, nitrile, halogen group, substituted or unsubstituted C1-C20 alkyl; substituted or unsubstituted C1-C20 alkoxy; substituted or unsubstituted C6-C30 aryl; substituted or unsubstituted C6-C30 heteroaryl, wherein the heteroatom is selected from oxygen, nitrogen, and sulfur;

[0040] Further preferred R0 is: hydrogen, deuterium, methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, phenyl, naphthyl, anthraceneyl, phenanthryl.

[0041] In general formula I, Ar3 and Ar4 may be the same or different from each other, and are selected from the following compounds respectively.

[0042]

[0043]

[0044] Where Z and R1-R4 are defined as above, and n5 is preferably 0 or 1;

[0045] R5 is selected from deuterium, nitrile, halogen group, substituted or unsubstituted C1-C20 alkyl; substituted or unsubstituted C1-C20 alkoxy; substituted or unsubstituted C6-C30 aryl; substituted or unsubstituted C6-C30 heteroaryl, wherein the heteroatom is selected from oxygen, nitrogen, and sulfur.

[0046] Furthermore, R5 is preferably one of the following compounds:

[0047]

[0048] In the above formula, * represents a connection point, and --- represents a fused ring chemical bond.

[0049] In this description, “substitution” means substitution by one, two or more substituents selected from the following: deuterium, nitrile, halogen group, C1-C20 alkyl, C1-C20 alkoxy, C6-C30 aryl, C6-C30 heteroaryl, wherein the heteroatom is selected from oxygen, nitrogen, and sulfur.

[0050] Furthermore, a more preferred general formula I is as follows:

[0051]

[0052] In the formula, Z, R0, and n0 are as defined above.

[0053] Furthermore, among the above-mentioned polycyclic aromatic compounds, any one of the compounds shown in the following structural formulas is selected:

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061] The polycyclic aromatic compounds of the present invention can be prepared by synthetic methods known to those skilled in the art. Alternatively, the following reaction process is preferred for preparation.

[0062]

[0063] Specific preparation method:

[0064] Step 1 specifically includes the following steps: Under nitrogen protection, raw material A (1.0 eq) and raw material B (1.0 eq) are dissolved in toluene solution, sodium tert-butoxide (2.00 eq), tris(dibenzylacetone)dipalladium (0.01 eq), and tri-tert-butylphosphine (0.05 eq) are added, stirred evenly, heated to 110℃, and refluxed for 8 hours; after the reaction is completed, the temperature is slightly lowered, and the mixture is filtered with diatomaceous earth to remove salt and catalyst. After the filtrate is cooled to room temperature, it is washed three times with water, and the organic phase is retained. Then, the aqueous phase is extracted with ethyl acetate; after combining the organic phases, the mixture is dried with anhydrous magnesium sulfate, and the solvent is removed using a rotary evaporator. The mixture is then dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake is washed multiple times with petroleum ether and dried in a 60℃ oven for 5 hours to obtain intermediate 1;

[0065] Step 2 specifically includes the following steps:

[0066] Under nitrogen protection, raw material D (1.0 eq) and raw material C (1.0 eq) were dissolved in toluene solution, and sodium tert-butoxide (2.00 eq), tris(dibenzylacetone)dipalladium (0.01 eq), and tri-tert-butylphosphine (0.05 eq) were added. The mixture was stirred until homogeneous, heated to 120 °C, and refluxed for 10 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The mixture was dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake was washed multiple times with petroleum ether and dried in a 60 °C oven for 7 h to obtain intermediate 2.

[0067] Step 3 specifically includes the following steps:

[0068] Under nitrogen protection, intermediate 1 (1.0 eq) and starting material E (1.0 eq) were dissolved in toluene solution, and sodium tert-butoxide (2.00 eq), tris(dibenzylacetone)dipalladium (0.01 eq), and tri-tert-butylphosphine (0.05 eq) were added. The mixture was stirred until homogeneous, heated to 120 °C, and refluxed for 6 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The organic phases were combined and dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V = 1:10) to obtain intermediate 3.

[0069] Step 4 specifically includes the following steps:

[0070] Under nitrogen protection, intermediates 2 (1.0 eq) and 3 (1.0 eq) were dissolved in toluene solution, and sodium tert-butoxide (2.00 eq), tris(dibenzylacetone)dipalladium (0.01 eq), and tri-tert-butylphosphine (0.05 eq) were added. The mixture was stirred until homogeneous, heated to 120 °C, and refluxed for 10 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V = 1:6) to obtain intermediate 4.

[0071] Step 5 specifically includes the following steps:

[0072] Under a nitrogen atmosphere, intermediate 5 (1.0 eq) and anhydrous tert-butylbenzene were placed in a reaction flask, and the nitrogen atmosphere was replaced. At -78°C, a pentane solution of tert-butyllithium (5.0 eq) was added dropwise to the reaction system. After the addition was complete, the temperature was slowly raised to 65°C and stirred for 3 h. The temperature was then lowered to -30°C, and boron tribromide (5.0 eq) was added dropwise. The temperature was raised to room temperature, and stirring was continued for 1 h. Then, N,N-diisopropylethylamine (10.0 eq) was added dropwise to the reaction system. The temperature was raised to 145°C and the reaction was continued for 4 h. After the reaction was completed, the mixture was cooled to room temperature, and a saturated aqueous solution of sodium bicarbonate was added dropwise to the reaction mixture. The mixture was then extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography (eluent: V(ethyl acetate):V(petroleum ether) = 1:20) to obtain chemical formula 1.

[0073] The present invention also provides an organic electroluminescent device, comprising a first electrode, a second electrode, and an organic layer located between the first and second electrodes. The organic layer comprises at least one layer selected from the following: a hole injection layer, a hole transport layer, a light-emitting auxiliary layer, a light-emitting layer, an electron transport layer, and an electron injection layer. At least one of the aforementioned compounds is contained within this organic layer. That is, the organic layer can be formed from a single compound represented by the above general formula I or a mixture of two or more compounds. Preferably, the single compound represented by the above general formula I or a mixture containing two or more compounds may be contained within the light-emitting layer.

[0074] The present invention does not limit the preparation method of the organic electroluminescent device; conventional methods in the art are acceptable. The present invention preferably uses methods such as thin film evaporation, electron beam evaporation, or physical vapor deposition to deposit metals and conductive oxides and their alloys on a substrate to form an anode, and then forms an organic layer and a cathode thereon to obtain an organic electroluminescent device.

[0075] The present invention also provides an optoelectronic device, which includes the above-described organic electroluminescent device.

[0076] Specifically, the aforementioned organic electroluminescent devices can be applied to organic light-emitting devices (OLEDs), organic solar cells (OSCs), electronic paper (e-paper), organic photosensitive materials (OPCs), or organic thin-film transistors (OTFTs), etc.

[0077] 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.

[0078] Additionally, it should be noted that the values ​​given in the following embodiments are as accurate as possible. However, those skilled in the art will understand that due to unavoidable measurement errors and experimental issues, each number should be understood as an approximation rather than an absolutely accurate value.

[0079] Example 1

[0080] The raw material A (A-3) involved in Example 1 and the raw material C (C-6) involved in Example 2 are not existing technologies and require the following three-step reaction synthesis preparation (the corresponding 1H NMR spectra of the prepared raw materials are shown in the figure). Figure 1 As shown):

[0081]

[0082] Preparation method of raw materials:

[0083] Dissolve raw material 1-1 (1.0 eq) in toluene solution, add raw material 1-2 (2.0 eq) at room temperature, stir well, and react for 10-11 h. After the reaction is completed, cool to room temperature and add water to the reaction solution to separate the reaction. Concentrate the organic layer and purify it by column chromatography (eluent: V (ethyl acetate): V (petroleum ether) = 1:2) to obtain intermediate 1-1.

[0084] Intermediate 1-1 (1.0 eq) was dissolved in THF solution at room temperature and stirred until homogeneous. MeMgBr (5.0 eq) was added dropwise at 0 to -10 °C. After the addition was complete, the reaction was carried out for 1-2 h. Then, the temperature was raised to 60-70 °C and the reaction was carried out for 8-10 h. After the reaction was completed, the temperature was lowered to room temperature, and saturated NH4Cl solution was added to the reaction solution to quench the reaction. The mixture was separated, and the organic layer was concentrated and purified by column chromatography (eluent: V(dichloromethane):V(petroleum ether) = 1:2) to obtain intermediate 1-2.

[0085] Intermediate 1-2 (1.0 eq) was dissolved in DCM solution at room temperature, and methanesulfonic acid (5.0 eq) was added at room temperature. The reaction was carried out for 4-6 hours. After the reaction was completed, water was added to the reaction solution and the mixture was separated. The solvent was removed by a rotary evaporator and then purified by column chromatography (eluent: V (dichloromethane): V (petroleum ether) = 1:4) to obtain the raw material.

[0086] The raw material B-3 involved in Example 1 was prepared via the following reaction route:

[0087]

[0088] The intermediate 1 involved in this embodiment is the same as intermediate 2, so it will not be repeated in the preparation route.

[0089] Preparation of compound 3:

[0090] In a mixed solution of toluene, ethanol, and water, B-1 (50.00 mmol) and B-2 (50.00 mmol) were added, followed by three purgings. Under nitrogen protection, potassium carbonate (100.00 mmol) and tetraphenylphosphine palladium (1.00 mmol) were added, stirred until homogeneous, and heated to 90 °C. The mixture was then refluxed for 6 h. After the reaction was complete, the temperature was slightly lowered, and the mixture was filtered through diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a solid organic compound. The solid organic compound was completely dissolved in a small amount of dichloromethane and then slowly added dropwise to a petroleum ether solution. After stirring until homogeneous, a precipitate formed. The precipitate was filtered to obtain a solid, which was washed successively with anhydrous ethanol and petroleum ether, and dried to obtain B-3 (11.48 g, yield 90.1%).

[0091]

[0092] Under nitrogen protection, raw materials A-3 (40.00 mmol) and B-3 (40.00 mmol) were dissolved in toluene solution, and sodium tert-butoxide (80.00 mmol), tris(dibenzylacetone)dipalladium (0.40 mmol), and tri-tert-butylphosphine (2.00 mmol) were added. The mixture was stirred until homogeneous, heated to 110 °C, and refluxed for 8 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salt and catalyst. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The organic phases were combined and dried with anhydrous magnesium sulfate. The solvent was removed using a rotary evaporator and dissolved in petroleum ether / ethanol for recrystallization. The mixture was filtered, and the filter cake was rinsed multiple times with petroleum ether and dried in a 60 °C oven for 5 h to obtain intermediate 1(2) (14.83 g, yield 78.64%).

[0093] Under nitrogen protection, intermediate 1 (30.00 mmol) and starting material E-3 (30.00 mmol) were dissolved in toluene solution, and sodium tert-butoxide (60.00 mmol), tris(dibenzylacetone)dipalladium (0.30 mmol), and tri-tert-butylphosphine (1.50 mmol) were added. The mixture was stirred until homogeneous, heated to 120 °C, and refluxed for 6 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The organic phases were combined and 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 = 1:10) to obtain intermediate 3 (14.72 g, yield 77.82%).

[0094] Under nitrogen protection, intermediates 2 (20.00 mmol) and 3 (20.00 mmol) were dissolved in toluene solution, and sodium tert-butoxide (40.00 mmol), tris(dibenzylacetone)dipalladium (0.20 mmol), and tri-tert-butylphosphine (1.00 mmol) were added. The mixture was stirred until homogeneous, heated to 120 °C, and refluxed for 10 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V = 1:6) to obtain intermediate 4 (13.63 g, yield 63.94%).

[0095] Under a nitrogen atmosphere, intermediate 4 (12.78 mmol) and anhydrous tert-butylbenzene were placed in a reaction flask, and the nitrogen atmosphere was purged. At -78 °C, a pentane solution of tert-butyllithium (63.90 mmol) was added dropwise to the reaction system. After the addition was complete, the temperature was slowly raised to 65 °C and stirred for 3 h. The temperature was then lowered to -30 °C, and boron tribromide (63.90 mmol) was added dropwise. The temperature was raised to room temperature, and stirring was continued for 1 h. N,N-diisopropylethylamine (127.80 mmol) was then added dropwise to the reaction system. The temperature was raised to 145 °C and the reaction was continued for 4 h. After the reaction was completed, the mixture was cooled to room temperature, and a saturated aqueous sodium bicarbonate solution was added dropwise to the reaction mixture. The mixture was then extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography (eluent: V(ethyl acetate):V(petroleum ether) = 1:20) to give compound 3 (4.73 g, yield 35.65%, MW: 1039.36).

[0096] The obtained compound 3 was analyzed, and the results are as follows:

[0097] HPLC purity: >99.6%.

[0098] Mass spectrometry test: theoretical value 1039.36; test value 1039.68.

[0099] Elemental analysis:

[0100] The calculated values ​​are: C, 82.05; H, 8.83; N, 8.09; B, 104.

[0101] The test values ​​are: C, 81.87; H, 9.15; N, 8.17; B, 1.13.

[0102] Nuclear magnetic resonance hydrogen spectrum: such as Figure 3 As shown.

[0103] Example 2

[0104] Preparation of compound 6:

[0105]

[0106] Under nitrogen protection, starting materials A-6 (40.00 mmol) and B-6 (40.00 mmol) were dissolved in toluene solution, and sodium tert-butoxide (80.00 mmol), tris(dibenzylacetone)dipalladium (0.40 mmol), and tri-tert-butylphosphine (2.00 mmol) were added. The mixture was stirred until homogeneous, heated to 110 °C, and refluxed for 8 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature, washed three times with water, and the organic phase was retained. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The mixture was then dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake was washed several times with petroleum ether and dried in a 60 °C oven for 5 h to obtain intermediate 1 (12.23 g, yield 81.26%).

[0107] Under nitrogen protection, starting materials D-6 (40.00 mmol) and C-6 (40.00 mmol) were dissolved in toluene solution, and sodium tert-butoxide (80.00 mmol), tris(dibenzylacetone)dipalladium (0.40 mmol), and tri-tert-butylphosphine (2.00 mmol) were added. The mixture was stirred until homogeneous, heated to 120 °C, and refluxed for 10 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature, washed three times with water, and the organic phase was retained. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The mixture was dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake was washed several times with petroleum ether and dried in a 60 °C oven for 7 h to obtain intermediate 2 (12.07 g, yield 80.19%).

[0108] Under nitrogen protection, intermediate 1 (30.00 mmol) and starting material E-6 (30.00 mmol) were dissolved in toluene solution, and sodium tert-butoxide (60.00 mmol), tris(dibenzylacetone)dipalladium (0.30 mmol), and tri-tert-butylphosphine (1.50 mmol) were added. The mixture was stirred until homogeneous, heated to 120 °C, and refluxed for 6 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The organic phases were combined and dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V = 1:10) to obtain intermediate 3 (12.83 g, yield 79.89%).

[0109] Under nitrogen protection, intermediates 2 (20.00 mmol) and 3 (20.00 mmol) were dissolved in toluene solution, and sodium tert-butoxide (40.00 mmol), tris(dibenzylacetone)dipalladium (0.20 mmol), and tri-tert-butylphosphine (1.00 mmol) were added. The mixture was stirred until homogeneous, heated to 120 °C, and refluxed for 10 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V = 1:6) to obtain intermediate 4 (11.55 g, yield 65.97%).

[0110] Under a nitrogen atmosphere, intermediate 4 (13.18 mmol) and anhydrous tert-butylbenzene were placed in a reaction flask, and the nitrogen atmosphere was replaced. At -78 °C, a pentane solution of tert-butyllithium (65.90 mmol) was added dropwise to the reaction system. After the addition was complete, the temperature was slowly raised to 65 °C and stirred for 3 h. The temperature was then lowered to -30 °C, and boron tribromide (65.90 mmol) was added dropwise. The temperature was raised to room temperature, and stirring was continued for 1 h. N,N-diisopropylethylamine (131.80 mmol) was then added dropwise to the reaction system. The temperature was raised to 145 °C and the reaction was continued for 4 h. After the reaction was completed, the mixture was cooled to room temperature, and a saturated aqueous sodium bicarbonate solution was added dropwise to the reaction mixture. The mixture was then extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography (eluent: V(ethyl acetate):V(petroleum ether) = 1:20) to give compound 6 (4.20 g, yield 37.59%, MW: 849.07).

[0111] The obtained compound 6 was analyzed, and the results are as follows:

[0112] HPLC purity: >99.6%.

[0113] Mass spectrometry test: theoretical value 849.07; test value 849.26.

[0114] Elemental analysis:

[0115] The calculated values ​​are: C, 83.46; H, 8.67; N, 6.60; B, 1.27.

[0116] The test values ​​are: C, 83.15; H, 8.81; N, 6.69; B, 1.30.

[0117] Nuclear magnetic resonance hydrogen spectrum: such as Figure 4 As shown.

[0118] Example 3

[0119] The raw materials A (A-45, A-68) involved in Examples 3 and 4 are not existing technologies and require the following 9-step reaction synthesis preparation (the corresponding 1H NMR spectra of the prepared raw materials are shown in the figure). Figure 2 As shown):

[0120]

[0121] Preparation method of raw materials:

[0122] Raw material 2-1 (1.0 eq) was dissolved in methanol solution at room temperature, then raw material 2-2 (1.0 eq) was added, followed by Cu2(OAc)2 (0.02 eq) and sodium methoxide (2.0 eq). The mixture was stirred until homogeneous, heated to 80-90℃, and refluxed for 6-7 h. After the reaction was completed, water was added to the reaction solution and extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography (eluent: V(ethyl acetate):V(petroleum ether) = 1:4) to obtain intermediate 2-1.

[0123] Intermediate 2-1 (1.0 eq) was dissolved in toluene solution, and raw material 2-3 (3.0 eq) was added at room temperature, followed by methanesulfonic acid (6.0 eq). The mixture was stirred until homogeneous, heated to 80-90℃, and refluxed for 10-11 h. After the reaction was completed, the mixture was cooled to room temperature and water was added to the reaction solution to separate the components. The organic layer was concentrated and purified by column chromatography (eluent: V(dichloromethane):V(petroleum ether) = 1:4) to obtain intermediate 2-2.

[0124] Intermediate 2-2 (1.0 eq) was dissolved in THF solution at room temperature and stirred until homogeneous. MeMgBr (5.0 eq) was added dropwise at 0 to -10℃. After the addition was complete, the reaction was carried out for 1-2 hours. Then, the temperature was raised to 60-70℃ and the reaction was carried out for 8-9 hours. After the reaction was completed, the temperature was lowered to room temperature, and saturated NH4Cl solution was added to the reaction solution to quench the reaction. The mixture was separated, and the organic layer was concentrated and purified by column chromatography (eluent: V(dichloromethane):V(petroleum ether) = 1:2) to obtain intermediate 2-3.

[0125] Intermediate 2-3 (1.0 eq) was dissolved in DCM solution at room temperature, and methanesulfonic acid (5.0 eq) was added at room temperature. The reaction was carried out for 54 h. After the reaction was completed, water was added to the reaction solution and the mixture was separated. The solvent was removed by a rotary evaporator, and methanol solution was added and stirred to precipitate a white solid, yielding intermediate 2-4.

[0126] Intermediate 2-4 (1.0 eq) was dissolved in methanol, and 6.0 mol HCl solution was added. The mixture was stirred at room temperature for 10-11 h. After the reaction was completed, water was added to the reaction solution and the mixture was extracted with ethyl acetate. The solvent was removed using a rotary evaporator to obtain a light yellow solid, which was intermediate 2-5.

[0127] Intermediate 2-5 (1.0 eq) was dissolved in methanol at room temperature, and starting material 2-4 (1.2 eq) and sodium methoxide (2.0 eq) were added. The reaction was carried out at room temperature for 1-2 h. After the reaction was completed, water was added to the reaction solution and extracted with DCM. The solvent was removed by a rotary evaporator, and the solution was purified by column chromatography (eluent: V(dichloromethane):V(petroleum ether) = 1:2) to obtain intermediate 2-6.

[0128] Intermediate 2-6 (1.0 eq) was dissolved in dichloromethane solution at room temperature, and trifluoroacetic acid (20 mL) and triethylsilane (1.0 eq) were added dropwise and stirred until homogeneous. The mixture was reacted at room temperature for 8-9 h. After the reaction was completed, saturated NH4Cl solution was added to the reaction solution and the mixture was separated. The organic layer was concentrated and purified by column chromatography (eluent: V(dichloromethane):V(petroleum ether) = 1:6) to obtain intermediate 2-7.

[0129] Intermediate 2-7 (1.0 eq) was dissolved in THF solution at room temperature and stirred until homogeneous. MeMgBr (5.0 eq) was added dropwise at 0 to -10℃. After the addition was complete, the reaction was carried out for 1-2 hours. Then, the temperature was raised to 60-80℃ and the reaction was carried out for 8-10 hours. After the reaction was completed, the temperature was lowered to room temperature, and saturated NH4Cl solution was added to the reaction solution to quench the reaction. The mixture was separated, and the organic layer was concentrated and purified by column chromatography (eluent: V(dichloromethane):V(petroleum ether) = 1:2) to obtain intermediate 2-8.

[0130] Intermediate 2-8 (1.0 eq) was dissolved in DCM solution at room temperature and stirred until homogeneous. Methylsulfonic acid (5.0 eq) was added and reacted for 4-5 hours. After the reaction was completed, water was added to the reaction solution and the mixture was separated. The solvent was removed using a rotary evaporator, and methanol solution was added and stirred to precipitate a light yellow solid, which yielded the raw material.

[0131] Preparation of compound 45:

[0132]

[0133] Under nitrogen protection, raw materials A-45 (40.00 mmol) and B-45 (40.00 mmol) were dissolved in toluene solution, and sodium tert-butoxide (80.00 mmol), tris(dibenzylacetone)dipalladium (0.40 mmol), and tri-tert-butylphosphine (2.00 mmol) were added. The mixture was stirred until homogeneous, heated to 110 °C, and refluxed for 8 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature, washed three times with water, and the organic phase was retained. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The mixture was then dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake was washed several times with petroleum ether and dried in a 60 °C oven for 5 h to obtain intermediate 1 (13.77 g, yield 79.81%).

[0134] Under nitrogen protection, starting materials D-45 (40.00 mmol) and C-45 (40.00 mmol) were dissolved in toluene solution, and sodium tert-butoxide (80.00 mmol), tris(dibenzylacetone)dipalladium (0.40 mmol), and tri-tert-butylphosphine (2.00 mmol) were added. The mixture was stirred until homogeneous, heated to 120 °C, and refluxed for 10 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature, washed three times with water, and the organic phase was retained. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The mixture was dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake was washed several times with petroleum ether and dried in a 60 °C oven for 7 h to obtain intermediate 2 (10.97 g, yield 81.33%).

[0135] Under nitrogen protection, intermediate 1 (30.00 mmol) and starting material E-45 (30.00 mmol) were dissolved in toluene solution, and sodium tert-butoxide (60.00 mmol), tris(dibenzylacetone)dipalladium (0.30 mmol), and tri-tert-butylphosphine (1.50 mmol) were added. The mixture was stirred until homogeneous, heated to 120 °C, and refluxed for 6 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases 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 = 1:10) to obtain intermediate 3 (13.93 g, yield 78.64%).

[0136] Under nitrogen protection, intermediates 2 (20.00 mmol) and 3 (20.00 mmol) were dissolved in toluene solution, and sodium tert-butoxide (40.00 mmol), tris(dibenzylacetone)dipalladium (0.20 mmol), and tri-tert-butylphosphine (1.00 mmol) were added. The mixture was stirred until homogeneous, heated to 120 °C, and refluxed for 10 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V = 1:6) to obtain intermediate 4 (12.09 g, yield 67.85%).

[0137] Under a nitrogen atmosphere, intermediate 4 (13.55 mmol) and anhydrous tert-butylbenzene were placed in a reaction flask, and the nitrogen atmosphere was purged. At -78 °C, a pentane solution of tert-butyllithium (67.75 mmol) was added dropwise to the reaction system. After the addition was complete, the temperature was slowly raised to 65 °C and stirred for 3 h. The temperature was then lowered to -30 °C, and boron tribromide (67.75 mmol) was added dropwise. The temperature was raised to room temperature, and stirring was continued for 1 h. N,N-diisopropylethylamine (135.50 mmol) was then added dropwise to the reaction system. The temperature was raised to 145 °C and the reaction was continued for 4 h. After the reaction was completed, the mixture was cooled to room temperature, and a saturated sodium bicarbonate aqueous solution was added dropwise to the reaction mixture. The mixture was then extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography (eluent: V(ethyl acetate):V(petroleum ether) = 1:20) to give compound 45 (4.13 g, yield 35.27%, MW: 865.15).

[0138] The obtained compound 45 was analyzed, and the results are as follows:

[0139] HPLC purity: >99.6%.

[0140] Mass spectrometry test: theoretical value 865.15; test value 865.38.

[0141] Elemental analysis:

[0142] The calculated values ​​are: C, 86.08; H, 9.44; N, 3.24; B, 1.25.

[0143] The test values ​​are: C, 85.88; H, 9.58; N, 3.46; B, 1.22.

[0144] Example 4

[0145] Preparation of compound 68:

[0146]

[0147] Under nitrogen protection, raw materials A-68 (40.00 mmol) and B-68 (40.00 mmol) were dissolved in toluene solution, and sodium tert-butoxide (80.00 mmol), tris(dibenzylacetone)dipalladium (0.40 mmol), and tri-tert-butylphosphine (2.00 mmol) were added. The mixture was stirred until homogeneous, heated to 110 °C, and refluxed for 8 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature, washed three times with water, and the organic phase was retained. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The mixture was then dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake was washed several times with petroleum ether and dried in a 60 °C oven for 5 h to obtain intermediate 1 (11.85 g, yield 78.92%).

[0148] Under nitrogen protection, starting materials D-68 (40.00 mmol) and C-68 (40.00 mmol) were dissolved in toluene solution, and sodium tert-butoxide (80.00 mmol), tris(dibenzylacetone)dipalladium (0.40 mmol), and tri-tert-butylphosphine (2.00 mmol) were added. The mixture was stirred until homogeneous, heated to 120 °C, and refluxed for 10 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature, washed three times with water, and the organic phase was retained. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The mixture was dissolved in petroleum ether / ethanol, recrystallized, filtered, and the filter cake was washed several times with petroleum ether and dried in a 60 °C oven for 7 h to obtain intermediate 2 (10.98 g, yield 81.34%).

[0149] Under nitrogen protection, intermediate 1 (30.00 mmol) and starting material E (30.00 mmol) were dissolved in toluene solution, and sodium tert-butoxide (60.00 mmol), tris(dibenzylacetone)dipalladium (0.30 mmol), and tri-tert-butylphosphine (1.50 mmol) were added. The mixture was stirred until homogeneous, heated to 120 °C, and refluxed for 6 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V = 1:10) to obtain intermediate 3 (12.47 g, yield 77.85%).

[0150] Under nitrogen protection, intermediates 2 (20.00 mmol) and 3 (20.00 mmol) were dissolved in toluene solution, and sodium tert-butoxide (40.00 mmol), tris(dibenzylacetone)dipalladium (0.20 mmol), and tri-tert-butylphosphine (1.00 mmol) were added. The mixture was stirred until homogeneous, heated to 120 °C, and refluxed for 10 h. After the reaction was completed, the temperature was slightly lowered, and the mixture was filtered with diatomaceous earth to remove salts and catalysts. The filtrate was cooled to room temperature and washed three times with water, retaining the organic phase. The aqueous phase was then extracted with ethyl acetate. The combined organic phases were dried with anhydrous magnesium sulfate, and the solvent was removed using a rotary evaporator. The remaining substances were purified by column chromatography using a mixed solution of dichloromethane and petroleum ether (V:V = 1:6) to obtain intermediate 4 (10.57 g, yield 63.29%).

[0151] Under a nitrogen atmosphere, intermediate 4 (12.64 mmol) and anhydrous tert-butylbenzene were placed in a reaction flask, and the nitrogen atmosphere was purged. At -78 °C, a pentane solution of tert-butyllithium (63.20 mmol) was added dropwise to the reaction system. After the addition was complete, the temperature was slowly raised to 65 °C and stirred for 3 h. The temperature was then lowered to -30 °C, and boron tribromide (63.20 mmol) was added dropwise. The temperature was raised to room temperature, and stirring was continued for 1 h. N,N-diisopropylethylamine (126.40 mmol) was then added dropwise to the reaction system. The temperature was raised to 145 °C and the reaction was continued for 4 h. After the reaction was completed, the mixture was cooled to room temperature, and a saturated aqueous sodium bicarbonate solution was added dropwise to the reaction mixture. The mixture was then extracted with ethyl acetate. The organic layer was concentrated and purified by column chromatography (eluent: V(ethyl acetate):V(petroleum ether) = 1:20) to give compound 68 (3.62 g, yield 35.45%, MW: 809.05).

[0152] The obtained compound 68 was analyzed, and the results are as follows:

[0153] HPLC purity: >99.6%.

[0154] Mass spectrometry test: theoretical value 809.05; test value 809.33.

[0155] Elemental analysis:

[0156] The calculated values ​​are: C, 86.11; H, 9.10; N, 3.46; B, 1.34.

[0157] The test values ​​are: C, 85.98; H, 9.34; N, 3.64; B, 1.37.

[0158] The synthesis methods for other compounds are the same as those in the above examples, and will not be described in detail here. The mass spectra, molecular formulas, and yields of other synthetic examples are shown in Table 1 below:

[0159] Table 1 Mass spectrometry analysis and yield of the examples.

[0160] Example 1 C71H91BN6 1039.36 1039.68 35.65 Example 2 C59H73BN4 849.07 849.26 37.59 Example 3 C62H81BN2 865.15 865.38 35.27 Example 4 C58H73BN2 809.05 809.33 35.45 Compound 1 C65H82BN5 944.22 944.46 36.19 Compound 5 C66H83BN4 943.23 943.02 32.58 Compound 9 C81H99BN2 1111.51 1111.26 30.59 Compound 14 C61H75BN2 847.1 847.36 38.68 Compound 17 C57H72BN3 810.03 810.31 33.16 Compound 21 C85H107BN2 1167.62 1167.36 29.65 Compound 24 C73H88BN3 1018.34 1018.59 30.24 Compound 30 C73H95BN2 1011.39 1011.16 28.91 Compound 35 C87H113BN4 1225.7 1225.46 25.67 Compound 39 C69H81BN2 949.23 949.51 31.26 Compound 43 C83H103BN2 1139.56 1139.25 29.33 Compound 48 C79H97BN2O 1101.47 1101.26 28.57 Compound 52 C67H78BN3S 968.25 968.05 29.11 Compound 56 C81H100BN3 1126.52 1126.29 29.48 Compound 60 C54H56BN3 757.87 757.64 34.99 Compound 65 C65H74BN3 908.14 908.37 30.61 Compound 69 C55H67BN2 766.97 767.13 32.55 Compound 73 C66H90BN3 936.28 936.45 31.94 Compound 78 C75H99BN6 1095.47 1095.66 27.65 Compound 82 C81H101BN4 1141.54 1141.31 29.03 Compound 87 C84H99BN2O 1163.54 1163.21 30.21 Compound 92 C68H89BN2 945.28 945.06 29.34 Compound 98 C56H66D3BN2 784.01 784.29 34.68 Compound 104 C58H70D3BN2 812.06 812.34 32.57 Compound 108 C67H83BN2 927.23 927.47 30.67

[0161] Device Example 1: Fabrication of an organic electroluminescent device containing compound 3

[0162] a. ITO Anode: An ITO (Indium Tin Oxide)-Ag-ITO (Indium Tin Oxide) glass substrate with a coating thickness of 150nm is cleaned twice in distilled water, ultrasonically washed for 30 minutes, then repeatedly cleaned twice with distilled water, ultrasonically washed for 10 minutes. After washing, it is transferred to a spin dryer for drying, and finally baked in a vacuum oven at 220℃ for 2 hours. After baking, it is cooled before use. Using this substrate as the anode, a vapor deposition process is performed to deposit other functional layers sequentially on it.

[0163] b. HIL (Hole Injection Layer): The evaporation rate of the hole injection layer material HT-1 and P-dopant was determined by vacuum evaporation, and their chemical formulas are shown below. The evaporation rate ratio of HT-1 to P-dopant was 97:3, and the thickness was 10 nm.

[0164] c. HTL (Hole Transport Layer): At a certain evaporation rate, HT-1 of 130 nm was vacuum-deposited on the hole injection layer as a hole transport layer, and the structure is shown in the figure.

[0165] d. Light-emitting auxiliary layer: with At a certain evaporation rate, a 10nm EBL-1 layer was vacuum-deposited on the hole transport layer as a light-emitting auxiliary layer.

[0166] e. EML (Emitting Layer): Then, on the above-mentioned emitting auxiliary layer, with... The evaporation rate was determined by vacuum evaporation of a host material with a thickness of 20 nm and compound 3 provided in the above embodiment as a dopant as the light-emitting layer. The chemical formula of the host is shown below. The evaporation rate ratio of the host to the dopant is 98:2.

[0167] f. HBL (Hole Blocking Layer): At a certain evaporation rate, a 5nm HB-1 layer was vacuum-deposited on the light-emitting layer as a hole-blocking layer, as shown in the figure:

[0168] g. ETL (Electron Transport Layer): At a certain evaporation rate, 30 nm of ET-1 was vacuum-deposited on the hole blocking layer as an electron transport layer.

[0169] h, EIL (Electron Injection Layer): with The evaporation rate was such that a Yb film layer of 1.0 nm was deposited to form an electron injection layer.

[0170] i. Cathode: with The evaporation rate ratio of magnesium and silver at 18nm was 1:9, resulting in an OLED device.

[0171] j. Optical extraction layer: with The evaporation rate was adjusted to vacuum-deposit a 70nm thick CPL-1 layer on the cathode as a light extraction layer. The deposited substrate was then encapsulated. First, a UV adhesive was applied to the cleaned cover plate using a coating machine. Then, the coated cover plate was moved to the lamination section, and the evaporated substrate was placed on top of the cover plate. Finally, the substrate and cover plate were bonded together using a bonding machine, while simultaneously curing the UV adhesive.

[0172] The required material structure is shown below:

[0173]

[0174] Device Examples 2-29: Following the method described above, compound 3 used in Device Example 1 was replaced with compounds 1, 5, 6, 9, 14, 17, 21, 24, 30, 35, 39, 43, 45, 48, 52, 56, 60, 65, 68, 69, 73, 78, 82, 87, 92, 98, 104, and 108 as doping materials to prepare the corresponding organic electroluminescent devices.

[0175] Comparative Examples: This comparative example provides an organic electroluminescent device. The only difference between this organic electroluminescent device and Device Example 1 is that the organic electroluminescent device is prepared by evaporation using existing comparative compounds a, b, c, and d instead of the doping materials in Device Example 1. Comparative Examples 1 to 4 are prepared accordingly. The chemical structural formulas of comparative compounds a, b, c, and d are as follows:

[0176]

[0177] The driving voltage, luminous efficiency, BI value, and lifetime of the organic electroluminescent devices obtained in Examples 1-29 and Comparative Examples 1-4 were characterized at a brightness of 1000 nits. The test results are shown in Table 2 below:

[0178] Table 2 Device Test Results

[0179]

[0180]

[0181] Note: In blue top-emitting devices, current efficiency is greatly affected by chromaticity. Therefore, the influence of chromaticity on efficiency is taken into account, and the ratio of luminous efficiency to CIEy is defined as the BI value, i.e., BI = (cd / A) / CIEy.

[0182] As shown in the table above, the organic electroluminescent devices prepared using the compounds provided in this invention as doping materials in the light-emitting layer have significantly improved luminous efficiency and increased lifetime by 30-40 hours compared with the organic electroluminescent devices prepared using comparative compounds a-d (device comparative examples 1-4) as doping materials.

[0183] The full width at half maximum (FWHM) of the doped comparative compounds a to d (device comparative examples 1 to 4) differs from that of the compounds doped with the present invention. The compounds of the present invention have a narrower FWHM and excellent color purity.

[0184] The above description is merely a preferred embodiment of the present invention and is not intended to limit the invention. Various modifications and variations can be made to the present invention by those skilled in the art. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the scope of protection of the present invention.

[0185] 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 to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. A polycyclic aromatic compound, characterized in that, The structures of the polycyclic aromatic compounds are shown in general formula I: ； In general formula I, n0 is an integer between 0 and 3; R0 is methyl, deuterated methyl, tert-butyl, 2,2-dimethylbutyl, isopropyl, isopentyl, phenyl, or naphthyl. Ar1 and Ar2 may be the same or different from each other, and are independently compounds represented by Formula 1 and Formula 2 respectively, and at least one of Ar1 and Ar2 is Formula 1; ； Ar3 and Ar4 may be the same as or different from each other, and are each one of the following compounds: ； Z is either C or N; where, when Z is C, n1 is an integer from 0 to 13; when Z is N, n1 is an integer from 0 to 12. n2, n3, and n5 are either 0 or 1; R1 is selected from methyl; R2-R5 are independently methyl, tert-butyl, isopropyl, isopentyl, and 2,2-dimethylbutyl, respectively.

2. The polycyclic aromatic compound according to claim 1, characterized in that, Formula 1 is one of the following compounds:

3. The polycyclic aromatic compound according to claim 1, characterized in that, The polycyclic aromatic compound is one of the following compounds: 。 4. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes the polycyclic aromatic compounds as described in any one of claims 1-3.

5. A photoelectric device, characterized in that, The optoelectronic device includes the organic electroluminescent device as described in claim 4.

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