An organic compound containing a triazine structure and an electroluminescent device thereof

Abstract

This invention discloses an organic compound containing a triazine structure and its electroluminescent device, belonging to the field of organic light-emitting materials and semiconductor technology. The organic compound containing the triazine structure has the following structural formula. Applying this organic compound as the main light-emitting material to the light-emitting layer of an OLED device can improve the luminous efficiency of the electroluminescent device, reduce the start-up voltage and energy consumption, and extend the operating life of the electroluminescent device.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescent materials and semiconductor technology, specifically relating to an organic compound containing a triazine structure and its electroluminescent device. Background Technology

[0002] A typical organic light-emitting diode (OLED) usually consists of an anode, a cathode, and organic functional layers disposed between them, including a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, and an electron injection layer. Among these, the emissive layer is the core functional layer that enables electroluminescence, and its performance directly determines key indicators of the OLED device such as luminous efficiency, color purity, and lifetime. In the emissive layer, the host emissive material plays a crucial role in transporting charge carriers (holes or electrons), dispersing light from the guest emissive material, and restricting exciton recombination at the guest emissive material. Therefore, the selection of the host emissive material is critical to the performance of the emissive layer and the entire OLED device.

[0003] Based on carrier transport characteristics, host light-emitting materials are classified into hole-transporting host light-emitting materials and electron-transporting host light-emitting materials. For electron-transporting host light-emitting materials, they must possess good electron transport capabilities, matching highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energy levels with the guest light-emitting material, and high thermal and chemical stability to ensure efficient carrier transport and recombination and maintain device stability during operation. However, in existing technologies, traditional electron-transporting host light-emitting materials (such as compounds containing single heterocyclic structures like pyridine or quinoline rings) often suffer from low electron mobility, insufficient energy level matching with the guest light-emitting material, low thermal decomposition temperature, or poor chemical stability. This results in low luminous efficiency, high operating voltage, and short lifetime in OLED devices, making it difficult to meet the practical application requirements of high-performance OLED devices.

[0004] Therefore, developing novel electron transport-type host light-emitting materials with high electron transport performance, suitable energy level structure, and excellent thermal and chemical stability is of great research value and practical significance for further improving the overall performance of OLED devices, such as luminous efficiency, reducing operating voltage, and extending device lifespan. Summary of the Invention

[0005] To address the shortcomings of the prior art, the present invention aims to provide an organic compound containing a triazine structure and its electroluminescent device, wherein the organic compound is used as the main luminescent material in the luminescent layer, thereby solving the technical problem that the existing main luminescent materials still have insufficient luminous efficiency, stability and lifespan to meet market demands.

[0006] This invention is achieved through the following technical solution: In a first aspect, the present invention provides an organic compound containing a triazine structure, the structure of which is shown in formula (1):

[0007] In the formula: The main structure is Ar1, which is selected from any one of the following groups:

[0008] Among the above groups, This is the connection site between Ar1 and the main structure. This is the bonding site between Ar1 and R0; R0 is selected from any one of the following groups:

[0009] Among the above groups, " "This is the bonding site between R0 and Ar1.

[0010] Preferably, the triazine-containing organic compound is any one of compounds 1 to 157, with the following specific structural formulas:

[0011] In a second aspect, the present invention provides an electroluminescent device comprising an anode layer, a cathode layer, and an organic layer located between the anode layer and the cathode layer, the organic layer comprising a hole transport layer, a light-emitting layer, and an electron transport layer, the hole transport layer being located between the anode layer and the light-emitting layer, and the electron transport layer being located between the cathode layer and the light-emitting layer; the light-emitting layer comprises a host light-emitting material and a guest light-emitting material, the host light-emitting material comprising the above-described organic compound containing a triazine structure as shown in formula (1).

[0012] Preferably, the guest luminescent material is selected from phosphorescent materials. , and One of them, and the mass of the guest luminescent material accounts for 0.1% to 3.0% of the total mass of the luminescent layer.

[0013] Preferably, the electroluminescent device comprises, in sequence from the anode layer to the cathode layer, a substrate, an anode layer, a hole injection layer (HIL), a hole transport layer, an electron blocking layer (EBL), an emission material layer (EML), a hole blocking layer (HBL), an electron transport layer, an electron injection layer (EIL), and a cathode layer.

[0014] As a substrate, it needs to have the characteristics of high mechanical strength, excellent thermal stability, excellent water resistance, and excellent transparency.

[0015] As the anode layer, the anode material is preferably a material with a high work function in order to facilitate the injection of holes into the organic layer. Specific examples of anode materials that can be used in this invention include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; oxides such as zinc oxide, aluminum oxide, or tin dioxide; and conductive polymers such as polypyrrole and polyaniline.

[0016] As functional organic layers, hole injection layers, hole transport layers, electron blocking layers, light-emitting layers, hole blocking layers, electron transport layers, and electron injection layers can be formed through various means or methods such as vacuum thermal evaporation, spin coating, and printing. The compounds used for each organic layer, except for the light-emitting layer, can be small organic molecules, large organic molecules, polymers, or combinations thereof. The materials used for the hole injection layers, hole transport layers, electron blocking layers, hole blocking layers, electron transport layers, and electron injection layers are selected from industry-leading cost-effective materials for their respective functional layers. The compatibility between each functional layer needs to be determined through a series of tests and screening processes.

[0017] Preferably, the material of the hole injection layer of the present invention is... .

[0018] Preferably, the material of the hole transport layer of the present invention can be selected from one of the following materials: .

[0019] Preferably, the material of the electron blocking layer of the present invention is selected from one of the following materials: .

[0020] Preferably, the material of the hole-blocking layer of the present invention is selected from... One of them; Preferably, the material of the electron transport layer of the present invention is selected from one of the following materials: .

[0021] Preferably, the material of the electron injection layer of the present invention is LiQ: .

[0022] As the cathode layer, the cathode material is preferably a material with a low work function in order to facilitate the injection of electrons into the organic layer. Specific examples of cathode materials that can be used in this invention include metals or alloys thereof such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead; multilayer materials such as LiF-Al or LiO2-Al, Mg-Al, and Mg-Ag.

[0023] A third aspect of the present invention provides a method for fabricating the above-mentioned electroluminescent device, wherein an anode layer is adhered to a substrate after pretreatment and cleaning, and then a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer of predetermined thickness are sequentially vapor-deposited under low temperature conditions. A cathode layer is then sputtered at low temperature, and finally the test device is packaged using conventional device testing and packaging methods to obtain an organic electroluminescent device.

[0024] A fourth aspect of the present invention provides a display panel comprising the electroluminescent device described above.

[0025] Compared with the prior art, the present invention has the following beneficial effects: 1. The triazine-containing organic compound of the present invention has triazine as the main structure. The triazine core itself is an electron-deficient structure. Combined with the donor-acceptor (DA) interaction of the electron-donating group Ar1 and the electron-withdrawing group R0, the HOMO / LUMO energy levels of the molecule can be flexibly adjusted. At the same time, the F-π interaction of the F atom on the fluorinated benzene ring, plus the conjugated structure of DA, can construct a continuous intermolecular charge transport channel, reduce the charge transport barrier, reduce charge recombination loss, and improve exciton recombination efficiency.

[0026] 2. By rationally designing different donor and acceptor groups Ar1 and R0, the HOMO / LUMO energy levels of the host luminescent material can be precisely adjusted to meet the energy level matching requirements of the host and guest luminescent materials, thereby confining excitons to the guest luminescent molecules, avoiding interference from the luminescence of the host luminescent material itself, and thus improving the luminescence efficiency of the device.

[0027] 3. The electron-donating heteroaryl group of Ar1 has an electron-rich π orbital, which can serve as a "channel site" for hole transport. When the parent nucleus combines with electron-withdrawing groups of R0 (such as trifluoromethyl or cyano), an efficient electron transport path can be constructed. This achieves a balance in the transport rate of holes and electrons in the light-emitting layer, reduces the accumulation of charge at the electrode or light-emitting layer interface, reduces non-radiative recombination loss, and improves the current efficiency of the device.

[0028] 4. The rigid conjugated framework of the triazine core and fluorobenzene ring, combined with the steric hindrance of Ar1 and R0 groups, inhibits the π-π stacking of the molecule itself, reduces aggregation-induced quenching, and increases the stability of the thin film, thus extending the lifespan of the device while maintaining high luminous efficiency.

[0029] 5. Using the triazine-containing organic compound described in this invention as the main material of the light-emitting layer can improve the balance of holes and electrons in the light-emitting layer, broaden the recombination region of charge carriers, improve the luminous efficiency of the device, reduce the start-up voltage and energy consumption, extend the stability and working life of the electroluminescent device, and meet the application requirements of the device in different scenarios. Attached Figure Description

[0030] To more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0031] Figure 1 This is a cross-sectional view of the electroluminescent device of the present invention; Figure 2 The NMR spectrum of compound 2 synthesized in Example 1 of this invention; Figure 3 The NMR spectrum of compound 19 synthesized in Example 2 of this invention; Figure 4 The NMR spectrum of compound 30 synthesized in Example 3 of this invention; Figure 5 The NMR spectrum of compound 55 synthesized in Example 4 of this invention; Figure 6 The NMR spectrum of compound 70 synthesized in Example 5 of this invention.

[0032] Appendix Figure 1 Marker description 1-Substrate, 2-Anode layer, 3-Hole injection layer, 4-Hole transport layer, 5-Electron blocking layer, 6-Light emitting layer, 7-Hole blocking layer, 8-Electron transport layer, 9-Electron injection layer, 10-Cathode layer. Detailed Implementation

[0033] The following specific examples illustrate the implementation of the present invention. Those skilled in the art can easily understand other advantages and effects of the present invention from the content disclosed in this specification. The present invention can also be implemented or applied through other different specific embodiments, and various details in this specification can also be modified or changed based on different viewpoints and applications without departing from the spirit of the present invention.

[0034] It should be noted that the process equipment or apparatus not specifically specified in the following embodiments are all conventional equipment or apparatus in the art, and the experimental methods not specified in the embodiments are generally performed under conventional conditions or under conditions recommended by the manufacturer. All raw materials used in the embodiments are conventional commercially available products with specifications that are conventional in the art, unless otherwise stated.

[0035] The important reactants involved in this invention include:

[0036]

[0037] Compound preparation example 1 (synthesis of compound 2): Synthesis of key intermediate M1:

[0038] Procedure: Under nitrogen protection, 2,4-dibromo-6-chloro-1,3,5-triazine (27.1 g, 0.1 mol), (2-fluorophenyl)boric acid (28 g, 0.2 mol), Pd(PPh3)4 (2.3 g, 2 mmol), K2CO3 (34.6 g, 0.25 mol), 400 mL THF, and 100 mL H2O were added to a 1000 mL three-necked flask. The system was heated to reflux and reacted for 8 h until the reaction was complete. The reaction solution was extracted with toluene, washed with water, and separated. The organic phase was filtered through diatomaceous earth, and the filtrate was collected and concentrated under reduced pressure to obtain a crude solid product. The crude product was purified by silica gel column chromatography (petroleum ether / dichloromethane = 8:1) to obtain intermediate M1, totaling 23.6 g, with a yield of 78%. HPLC (High Performance Liquid Chromatography) showed a purity of 98%, and LC-MS (Liquid Chromatograph-Mass Spectrometer) showed a molecular weight of 303.0.

[0039] Synthesis of compound 2:

[0040] Step 1: Procedure: Under nitrogen protection, compound a1 (24.5 g, 0.1 mol), reactant r1 (28.4 g, 0.11 mol), Pd(PPh3)4 (1.1 g, 1 mmol), K2CO3 (34.6 g, 0.25 mol), 400 mL THF, and 100 mL H2O were added to a 1000 mL three-necked flask. The system was heated to reflux and reacted for 5 h until the reaction was complete. The reaction solution was extracted with toluene, washed with water, and separated. The organic phase was filtered through diatomaceous earth, and the filtrate was collected and concentrated under reduced pressure to obtain a crude solid. The crude product was purified by silica gel column chromatography (petroleum ether / dichloromethane = 8:1) to obtain intermediate 2-1, totaling 32.2 g, with a yield of 85%. HPLC purity was 98%, and LC-MS showed a molecular weight of 379.1.

[0041] Step Two: Procedure: Under nitrogen protection, add intermediate 2-1 (30.3 g, 0.08 mol), intermediate M1 (29.1 g, 96 mmol), S-phos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl) (0.66 g, 1.6 mmol), sodium tert-butoxide (19.2 g, 0.2 mol), and 500 mL of toluene to a 1000 mL three-necked flask. Stir until the solution is clear, then add Pd2(dba)3 (0.7 g, 0.8 mmol). The reaction solution was heated to 110℃ and reacted for 3 hours. After the reaction was complete, the mixture was filtered hot using diatomaceous earth. The filtrate was cooled to room temperature, washed with purified water, and separated. The organic phase was retained, and the aqueous phase was extracted with ethyl acetate. The organic phases were combined, dried over anhydrous magnesium sulfate, concentrated, and column filtered (petroleum ether / dichloromethane = 20:1) to give compound 2, weighing 45.2 g, with a yield of 87.5%, an HPLC purity of 98%, and a molecular weight of 646.1 as shown by LC-MS. The NMR spectrum of compound 2 is shown below. Figure 2 As shown.

[0042] 1H NMR data for compound 2: 1 H NMR (500 MHz, DMSO- d 6) δ 8.24-8.23(m, 1H),8.18 – 8.12 (m, 2H), 8.04 – 7.99 (m, 3H), 7.97-7.94 (m, 2H), 7.80 – 7.74 (m,2H), 7.51 – 7.42 (m, 3H), 7.39 – 7.28 (m, 5H).

[0043] Compound preparation example 2 (synthesis of compound 19):

[0044] Step 1: Procedure: Under nitrogen protection, reactants a4 (37.2 g, 0.1 mol), r16 (26.1 g, 0.15 mol), K2CO3 (34.6 g, 0.25 mol), Pd(PPh3)4 (2.3 g, 2 mmol), 400 mL THF, and 100 mL H2O were added to a 1000 mL three-necked flask. The system was heated to reflux and reacted for 5 h until the reaction was complete. The reaction solution was extracted with toluene, washed with water, and separated. The organic phase was filtered through diatomaceous earth, and the filtrate was collected and concentrated under reduced pressure to obtain a crude solid. The crude product was purified by silica gel column chromatography (petroleum ether / dichloromethane = 10:1) to obtain 28.1 g of intermediate 19-1, with a yield of 75%. The HPLC purity was 98%, and the molecular weight was 374.0 as shown by LC-MS.

[0045] Step Two: Procedure: Under nitrogen protection, add intermediate 19-1 (37.4 g, 0.1 mol), pinacol diboronate (30.5 g, 0.12 mol), potassium acetate (21.6 g, 0.22 mol), and 500 mL of 1,4-dioxane to a 1000 mL three-necked flask. After stirring, heat to 60 °C and add Pd(dppf)Cl2 (0.7 g, 1 mmol). Then continue heating to 100 °C and reflux for 3 h. After the reaction was completed, the reaction solution was filtered while hot, the filtrate was collected, concentrated under reduced pressure to dryness, dissolved in 200 mL of toluene, and then washed with water. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated. After passing the organic phase through a silica gel column, the column chromatography solution was concentrated again under reduced pressure until solid precipitates and then stopped. After cooling to 10℃ and crystallization was completed, the solution was filtered and dried to obtain 36.9 g of intermediate 19-2, with a yield of 87.3%, HPLC purity of 98%, and LC-MS showing a molecular weight of 422.2.

[0046] Step 3: Procedure: Under nitrogen protection, intermediate 19-2 (33.8 g, 0.08 mol), intermediate M1 (30.3 g, 0.1 mol), K2CO3 (33.2 g, 0.24 mol), Pd(PPh3)4 (0.9 g, 0.8 mmol), 400 mL THF, and 100 mL H2O were added to a 1000 mL three-necked flask. The system was heated to reflux and reacted for 5 h until the reaction was complete. The reaction solution was extracted with toluene, washed with water, and separated. The organic phase was filtered through diatomaceous earth, and the filtrate was collected and concentrated under reduced pressure to obtain a crude solid. The crude product was purified by silica gel column chromatography (petroleum ether / dichloromethane = 10:1) to obtain 31.6 g of compound 19, with a yield of 70.2%. The HPLC purity was 98%, and the molecular weight was 563.1 as shown by LC-MS. The NMR spectrum of compound 19 is shown below. Figure 3 As shown.

[0047] 1H NMR data for compound 19: 1H NMR (500 MHz, DMSO- d 6) δ 8.82 (d, J = 14.6Hz, 2H), 8.16 (s, 1H), 8.05 (s, 1H), 7.99 (s, 1H), 7.98–7.93 (m, 4H), 7.83(s, 1H), 7.72 (s, 1H), 7.53–7.46 (m, 3H), 7.32 (s, 1H), 7.29-7.25 (m, 2H), 7.20 (dd, J = 7.5, 2.0 Hz, 2H).

[0048] Compound preparation example 3 (synthesis of compound 30):

[0049] Step 1: Procedure: The synthesis of intermediate 30-1 was performed by referring to the synthesis of intermediate 19-1 from reactant a4. Reactant a15 (39.8 g, 0.1 mol) was used to replace a4 (37.2 g, 0.1 mol), and reactant r9 (24.5 g, 0.15 mol) was used to replace r16 (26.1 g, 0.15 mol) to obtain 28.0 g of intermediate 30-1, with a yield of 72%, HPLC purity of 98%, and LC-MS showing a molecular weight of 389.0.

[0050] Step Two: Procedure: The synthesis of intermediate 30-2 was performed by referring to the synthesis of intermediates 19-1 to 19-2. Intermediate 19-1 (37.4 g, 0.1 mol) was replaced with intermediate 30-1 (38.9 g, 0.1 mol) to obtain 38.7 g of intermediate 30-2, with a yield of 88.4%, HPLC purity of 98%, and LC-MS showing a molecular weight of 437.2.

[0051] Step 3: Procedure: The synthesis of compound 30 followed the same procedure as intermediate 19-2 to compound 19. Intermediate 19-2 (33.8 g, 0.08 mol) was replaced with intermediate 30-2 (35.0 g, 0.08 mol) to obtain 33.1 g of compound 30, yielding a yield of 71.5%. HPLC purity was 98%, and LC-MS showed a molecular weight of 578.2. The NMR spectrum of compound 30 is shown below. Figure 4 As shown.

[0052] 1H NMR data for compound 30: 1 H NMR (500 MHz, DMSO- d6) δ 8.20 (s, 1H), 8.01(s, 1H), 7.99–7.93 (m, 3H), 7.90 (s, 1H), 7.78 (s, 1H), 7.71 (s, 1H), 7.66(s, 1H), 7.53–7.46 (m, 3H), 7.35 (s, 1H), 7.33–7.23 (m, 3H), 7.20 (dd, J =7.5, 2.0 Hz, 2H), 1.55 (s, 6H).

[0053] Compound preparation example 4 (synthesis of compound 55):

[0054] Step 1: Procedure: Under nitrogen protection, compound a21 (36.6 g, 0.2 mol) and 400 mL of tetrahydrofuran solution were added to a 1000 mL three-necked flask. Stirring was started, and the temperature was lowered to 0 °C. N-bromosuccinimide (NBS) (35.6 g, 0.2 mol) was slowly added. The mixture was allowed to naturally warm to room temperature and reacted for 1 hour. After the reaction was complete, 200 mL of saturated ammonium chloride aqueous solution was added for quenching. Ethyl acetate was then added for extraction, followed by washing with water. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether / dichloromethane = 5:1) to give intermediate 55-1, totaling 39.6 g, with a yield of 75.8%, HPLC purity of 97%, and LC-MS showing a molecular weight of 261.0.

[0055] Step Two: Procedure: The synthesis of intermediate 55-2 was performed by referring to the synthesis of intermediate M1 from reactant 2,4-dibromo-6-chloro-1,3,5-triazine. Intermediate 55-1 (39.1 g, 0.15 mol) was used to replace 2,4-dibromo-6-chloro-1,3,5-triazine (27.1 g, 0.1 mol), and reactant b1 (52.2 g, 0.3 mol) was used to replace (2-fluorophenyl)boric acid (28 g, 0.2 mol) to obtain intermediate 55-2, totaling 39.1 g, with a yield of 83.7%, HPLC purity of 98%, and LC-MS showing a molecular weight of 311.0.

[0056] Step 3: Procedure: Under nitrogen protection, intermediate 55-2 (31.1 g, 0.1 mol), K2CO3 (27.6 g, 0.2 mol), and 400 mL of N-methyl-2-pyrrolidone solution were added to a 1000 mL three-necked flask. Stirring was started, and the mixture was heated to 140 °C and reacted for 1 hour. After the reaction was complete, the reaction system was cooled to room temperature and then slowly added to 1.2 L of water. A solid precipitated, which was then filtered. The filter cake was dissolved in 200 mL of dichloromethane, extracted with water, washed with water, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether / dichloromethane = 8:1) to obtain 21.8 g of intermediate 55-3, with a yield of 75%, HPLC purity of 98%, and LC-MS showing a molecular weight of 291.0.

[0057] Step Four: Procedure: The synthesis of intermediate 55-4 was performed by referring to the synthesis of intermediate 2-1 from compound a1. Intermediate 55-3 (29.1 g, 0.1 mol) was used to replace compound a1 (24.5 g, 0.1 mol), and reactant r10 (24.4 g, 0.11 mol) was used to replace r1 (28.4 g, 0.11 mol) to obtain 30.7 g of intermediate 55-4, with a yield of 70.9%, HPLC purity of 98%, and LC-MS showing a molecular weight of 433.1.

[0058] Step 5: Procedure: The synthesis of compound 55 followed the same procedure as intermediate 2-1 to compound 2. Intermediate 2-1 (30.3 g, 0.08 mol) was replaced with intermediate 55-4 (34.6 g, 0.08 mol) to yield 49.3 g of compound 55, with a yield of 88%, HPLC purity of 98%, and LC-MS showing a molecular weight of 700.2. The NMR spectrum of compound 55 is shown below. Figure 5 As shown.

[0059] 1H NMR data for compound 55: 1 H NMR (500 MHz, DMSO- d 6) δ 8.69 (s, 1H), 8.34 (dd, J = 7.3, 1.3 Hz, 1H), 8.28 (d, J = 2.2 Hz, 1H), 8.13 – 8.08 (m, 2H), 8.00 –7.91 (m, 4H), 7.87 (d, J = 6.8 Hz, 1H), 7.77 (t, J = 7.9 Hz, 1H), 7.73 (dd, J=8.0, 1.9 Hz, 1H), 7.68 (d, J = 1.8 Hz, 1H), 7.55 (d, J = 7.7 Hz, 1H), 7.50 –7.42 (m, 2H), 7.41 – 7.30 (m, 5H), 7.27-7.24(m, 1H).

[0060] Compound preparation example 5 (synthesis of compound 70):

[0061] Step 1: Procedure: The synthesis of intermediate 70-1 was performed by referring to the synthesis of intermediate 55-1 from reactant a21. Compound a22 (41.8 g, 0.2 mol) was used to replace a21 (36.6 g, 0.2 mol) to obtain 45.5 g of intermediate 70-1, with a yield of 79.2%, HPLC purity of 98%, and LC-MS showing a molecular weight of 287.0.

[0062] Step Two: Procedure: The synthesis of intermediate 70-2 was performed by referring to the synthesis of intermediates 55-1 to 55-2. Intermediate 55-1 (39.1g, 0.15mol) was replaced with intermediate 70-1 (43.1g, 0.15mol), and reactant b1 (52.2g, 0.3mol) was replaced with reactant b2 (57.0g, 0.3mol) to obtain 46.0g of intermediate 70-2, with a yield of 86.8%, HPLC purity of 98%, and LC-MS showing a molecular weight of 353.1.

[0063] Step 3: Procedure: Under nitrogen protection, intermediate 70-2 (35.3 g, 0.1 mol), K2CO3 (27.6 g, 0.2 mol), and 400 mL of N,N-dimethylacetamide solution were added to a 1000 mL three-necked flask. Stirring was initiated, followed by the addition of Pd(OAc)2 (2.25 g, 0.01 mol). The mixture was heated to 120 °C and reacted for 12 hours. After the reaction was complete, the reaction system was cooled to room temperature. The precipitated solid was filtered and washed with water. The filter cake was dissolved in dichloromethane and washed with water. The combined organic phases were concentrated under reduced pressure. The crude product was recrystallized from methanol to obtain 27.4 g of intermediate 70-3, with a yield of 86.4%, an HPLC purity of 98%, and a molecular weight of 317.1 as shown by LC-MS.

[0064] Step Four: Procedure: The synthesis of intermediate 70-4 was performed by referring to the synthesis of intermediate 2-1 from compound a1. Intermediate 70-3 (31.7 g, 0.1 mol) was used to replace compound a1 (24.5 g, 0.1 mol), and reactant r2 (28.4 g, 0.11 mol) was used to replace r1 (28.4 g, 0.11 mol) to obtain 37.3 g of intermediate 70-4, with a yield of 75.3%, HPLC purity of 98%, and LC-MS showing a molecular weight of 495.1.

[0065] Step 5: Procedure: The synthesis of compound 70 followed the same procedure as intermediate 2-1 to compound 2. Intermediate 2-1 (30.3 g, 0.08 mol) was replaced with intermediate 70-4 (39.6 g, 0.08 mol) to obtain 54.6 g of compound 70, with a yield of 89.6%, HPLC purity of 98%, and LC-MS showing a molecular weight of 762.2. The NMR spectrum of compound 70 is shown below. Figure 6 As shown.

[0066] 1H NMR data for compound 70: 1 H NMR (500 MHz, DMSO- d 6) δ 8.25 (d, J = 7.6 Hz, 1H), 8.04 (d, J = 2.2 Hz, 1H), 7.97-7.94 (m, 2H), 7.90 (s, 1H), 7.84 (dd, J =7.7, 2.0 Hz, 1H), 7.82 – 7.76 (m, 3H), 7.72 (dd, J = 10.6, 2.2 Hz, 1H), 7.60 –7.51 (m, 2H), 7.50 – 7.30 (m, 8H), 1.55 (s, 6H).

[0067] The synthesis of other compounds in this invention follows the same method as compounds 2, 19, 30, 55 and 70, except that reactants a, b and r are substituted accordingly.

[0068] The process of implementing organic electroluminescent devices is described below: Schematic diagrams of the electroluminescent devices in the various embodiments and comparative examples of this invention are shown below. Figure 1 As shown, it includes a substrate 1, an anode layer 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron transport layer 8, an electron injection layer 9, and a cathode layer 10.

[0069] Example 1 (Electroluminescent device containing compound 1) An electroluminescent device containing compound 1 comprises, in the direction from the anode layer to the cathode layer, a polyethylene terephthalate (PET) substrate, indium tin oxide (ITO) conductive glass, HI-1, HT-1, EB-1, light-emitting layer 6, HB-1, ET-1, Liq and Al; The light-emitting layer 6 comprises compound 1 and DP-2 in a mass ratio of 98:2.

[0070] The method for preparing the electroluminescent device containing compound 1 includes the following steps: 1. Using 1.5 mm PET plastic as substrate 1 and 130 nm ITO conductive glass as anode layer 2, the substrate is washed in sequence by alkaline washing, pure water washing, drying, and then ultraviolet-ozone washing to remove organic residues on the surface of the PET substrate and ITO conductive glass.

[0071] 2. A layer of ITO conductive glass is adhered to a PET substrate. Using a vacuum evaporation apparatus, a 5 nm thick HI-1 layer is deposited as a hole injection layer 3. Then, a 25 nm thick HT-1 layer is deposited as a hole transport layer 4. Subsequently, a 5 nm thick EB-1 layer is deposited as an electron blocking layer 5. On the EB-1 layer, a 40 nm thick light-emitting layer 6 is formed by compound 1 and DP-2 with a mass ratio of 98:2 is deposited. On the light-emitting layer 6, a 10 nm thick HB-1 layer is deposited as a hole blocking layer 7. Then, a 25 nm thick ET-1 layer is deposited as an electron transport layer 8. On the electron transport layer 8, a 10 nm thick Liq layer is deposited as an electron injection layer 9. After the electron injection layer 9 is deposited, a 100 nm thick Al layer is finally sputtered as a cathode layer 10 using a low-temperature sputtering method.

[0072] 3. Vacuum encapsulation of HI-1, HT-1, EB-1, light-emitting layer 6, HB-1, ET-1 and Liq layer to obtain an organic electroluminescent device.

[0073] Examples 2-20 The preparation method of Example 1 was followed, except that in Examples 2 to 20, compounds 2, 11, 19, 24, 30, 35, 41, 52, 55, 67, 70, 75, 77, 86, 90, 102, 111, 123, 135, 148 and 155 of the present invention were selected as the main luminescent materials of the luminescent layer 6.

[0074] Comparative Examples 1-3 The preparation method was carried out according to the device example 1, except that in comparative examples 1 to 3, compound 1 was replaced by H1, H2, and H3, respectively.

[0075] Detailed preparation methods for Comparative Examples 1-3: Comparative Example 1: PET substrate / ITO (130nm) / HI-1 (5nm) / HT-1 (25nm) / EB-1 (5nm) / H1:DP-2=98:2 (40nm)HB-1 (10nm) / ET-1 (25nm) / Liq (10nm) / Al (100nm); Comparative Example 2: PET substrate / ITO (130nm) / H1-1 (5nm) / HT-1 (25nm) / EB-1 (5nm) / H2:DP-2=98:2 (40nm)HB-1 (10nm) / ET-1 (25nm) / Liq (10nm) / Al (100nm); Comparative Example 3: PET substrate / ITO (130nm) / H1-1 (5nm) / HT-1 (25nm) / EB-1 (5nm) / H3:DP-2=98:2 (40nm)HB-1 (10nm) / ET-1 (25nm) / Liq (10nm) / Al (100nm).

[0076] The structural formulas of H1, H2, and H3 in Comparative Examples 1-3 are as follows: (CN107667102A) (CN114133400A) (CN107619412A) The electroluminescent devices from the above embodiments and comparative examples were fabricated into 40 mm × 40 mm samples. Then, under the same device fabrication process conditions, the anode and cathode were connected using an industry-known driving circuit. The luminous performance indicators of each electroluminescent device were tested at 10 mA / cm². 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm². 2 The time required for the brightness to return to 95% of its initial brightness at a given current density (LT95, i.e., lifetime) was measured. The test results are shown in Table 1.

[0077] Table 1

[0078] As can be seen from the test data in Table 1, compared with existing electroluminescent devices made of host luminescent materials (Comparative Examples 1-3), when the compound of the present invention is used as the host luminescent material in the electroluminescent device, the lifespan and efficiency of the device are improved. At a low driving voltage of less than 3.5V, the current efficiency (cd / A) of the electroluminescent device is improved by at least 50%, and the time consumed for brightness reduction is more than 120 hours, showing excellent luminescent performance and lifespan.

[0079] The above content is only for illustrating the technical concept of the present invention and should not be construed as limiting the scope of protection of the present invention. Any modifications made to the technical solution based on the technical concept proposed in this invention shall fall within the scope of protection of the claims of this invention.

Claims

1. An organic compound containing a triazine structure, characterized in that, Its structure is shown in equation (1): In the formula: The main structure is Ar1, which is selected from any one of the following groups: Among the above groups, This is the connection site between Ar1 and the main structure. This is the bonding site between Ar1 and R0; R0 is selected from any one of the following groups: Among the above groups, " "This is the bonding site between R0 and Ar1.

2. The triazine-containing organic compound according to claim 1, characterized in that, Ar1 is selected from any one of the following groups: 。 3. The triazine-containing organic compound according to claim 1, characterized in that, R0 is selected from any one of the following groups: 。 4. The triazine-containing organic compound according to claim 1, characterized in that, It is any one of the following compounds 1 to 157: 。 5. An electroluminescent device, characterized in that, It includes an anode layer, a cathode layer, and an organic layer located between the anode layer and the cathode layer. The organic layer includes a hole transport layer, a light-emitting layer, and an electron transport layer. The hole transport layer is located between the anode layer and the light-emitting layer, and the electron transport layer is located between the cathode layer and the light-emitting layer. The components of the light-emitting layer include a host light-emitting material and a guest light-emitting material. The host light-emitting material includes the triazine-containing organic compound as described in any one of claims 1 to 4.

6. The electroluminescent device according to claim 5, characterized in that, The object luminescent material is selected from , and One of them.

7. The electroluminescent device according to claim 5, characterized in that, The mass of the guest luminescent material accounts for 0.1% to 3.0% of the mass of the luminescent layer.

8. The electroluminescent device according to claim 5, characterized in that, The material of the hole transport layer is selected from one of the following materials: 。 9. The electroluminescent device according to claim 5, characterized in that, The material of the electron transport layer is selected from one of the following materials: .

10. The electroluminescent device according to claim 5, characterized in that, From the anode layer to the cathode layer, the structure consists of, in sequence, the anode layer, the hole injection layer, the hole transport layer, the electron blocking layer, the light-emitting layer, the hole blocking layer, the electron transport layer, the electron injection layer, and the cathode layer.

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