Host material, organic electroluminescent material containing double hosts and organic electroluminescent device

Abstract

According to the main body material, the organic electroluminescent material containing the double main bodies and the organic electroluminescent device, the main body material contains a triarylamine structure and dibenzofuran binaphthyl, the physical and thermal stability of a compound of the triarylamine structure is good, crystallization and aggregation among molecules are not prone to occurring, and the service life is effectively prolonged; the HOMO / LUMO energy level of the material can be adjusted by introducing a triarylamine structure, and the energy level of the material is better matched with the energy level of other materials; the total reflection loss and waveguide loss of a traditional OLED device can be effectively reduced, and the luminous efficiency is improved. The dibenzofuran binaphthalene can improve the fluorescence quantum yield, and has good thermal stability and a proper energy level structure; the triazine structure has relatively good stability and relatively strong electron accepting capability, energy required during electron injection is reduced, and the voltage required for working of the device is reduced; when the luminescent material is used for the organic electroluminescent device, the driving voltage of the organic electroluminescent device is reduced, the efficiency of the device can be improved, and the service life of the device can be prolonged.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of organic electroluminescent materials, and particularly relates to a host material, an organic electroluminescent material containing a double host, and an organic electroluminescent device. BACKGROUND

[0002] Organic Light Emitting Diode (OLED) technology uses organic materials as the light-emitting layer, and has the advantages of low driving voltage, high brightness, high efficiency, and the ability to realize large-area flat panel color display. The principle of organic electroluminescence is based on when a voltage is applied to an organic material, electrons and holes are injected into the organic layer from the cathode and anode, respectively, and recombine in the light-emitting layer to form excitons. In the relaxation process, the excitons release energy and produce photons, thereby realizing light emission. In recent years, the research on organic electroluminescence technology has made significant progress, including improving the efficiency, lifetime and brightness of the device, reducing the cost and realizing a wider color gamut. These advances make organic electroluminescence technology have a wide application prospect in the fields of display and lighting.

[0003] The efficiency of organic electroluminescence (OLED) generally refers to the ability of the device to convert electrical energy into light energy, and is mainly divided into internal quantum efficiency and external quantum efficiency. Internal quantum efficiency refers to the light-emitting efficiency of exciton recombination in the light-emitting layer, while external quantum efficiency refers to the ratio of the number of photons extracted from the device to the number of electrons injected into the device.

[0004] The technical problems of the current organic electroluminescent device mainly include the following aspects: 1) Efficiency problem: The light-emitting efficiency of the organic electroluminescent device is relatively low and needs to be further improved.

[0005] 2) Lifetime problem: The stability and durability of organic materials are poor, resulting in short device lifetime.

[0006] 3) Color stability problem: The color of organic materials is easily affected by environmental factors such as temperature and humidity, resulting in unstable color.

[0007] 4) Manufacturing process problem: The manufacturing process of the organic electroluminescent device is relatively complex and needs to be further optimized.

[0008] 5) Cost problem: The cost of organic materials and manufacturing processes is relatively high, which limits the large-scale application of organic electroluminescent devices.

[0009] The use of a double-host system in an organic electroluminescent material has the following advantages: different host materials have different transport capabilities for electrons and holes, the double-host system can balance the transport of electrons and holes in the light-emitting layer by reasonable collocation, improve the formation efficiency of excitons, reduce exciton quenching, and thus improve the luminous efficiency and performance of the device. The energy transfer process between the double-hosts can effectively transfer the excited state energy to the light-emitting guest, widening the channel of energy transfer, which helps to improve the energy transfer efficiency and thus enhance the light-emitting effect. The double-host system can disperse stress, reduce the formation of crystal defects and aggregate state, thereby improving the stability and lifetime of the organic electroluminescent device and reducing the speed of device aging and degradation.

[0010] Therefore, how to develop a long-life, low driving voltage organic electroluminescent material containing double-host and an organic electroluminescent device is a technical problem that those skilled in the art need to solve. SUMMARY

[0011] In view of the deficiencies of the prior art, the purpose of the present application is to provide a host material, an organic electroluminescent material containing double-host and an organic electroluminescent device. The host material or the organic electroluminescent material containing double-host applied to the organic electroluminescent device can reduce the driving voltage of the device, improve the luminous efficiency and prolong the service life.

[0012] To achieve the purpose of the present application, the following technical solutions are adopted: In one aspect, the present application provides a host material, which is a compound having the structure shown in general formula one:

[0013] wherein, L0, L1 are a connecting bond, a substituted or unsubstituted C6-C30 arylamine group, a substituted or unsubstituted C3-C30 heteroarylamine group, a substituted or unsubstituted C6-C30 aryl group, a substituted or unsubstituted C3-C30 heteroaryl group, and the heteroatom is selected from one or more of oxygen, nitrogen and sulfur; Ar is selected from the following structures: ; wherein, represents a connecting site; A is selected from substituted or unsubstituted benzene or naphthalene; R1 is selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted phosphine oxide, substituted or unsubstituted silane, substituted or unsubstituted C6-C42 aryl, and substituted or unsubstituted C3-C42 heteroaryl, and the heteroatom is selected from one or more of oxygen, nitrogen, sulfur, silicon and selenium; R2 is selected from the following groups:

[0014] Any point can be a connection point.

[0015] In one embodiment of the present invention, general formula one has the following two structures: ; L0 and L1 are connecting bonds, substituted or unsubstituted C6-C18 aromatic amino groups, substituted or unsubstituted C3-C18 heteroaromatic amino groups, substituted or unsubstituted C6-C18 aryl groups, and substituted or unsubstituted C3-C18 heteroaromatic groups, wherein the heteroatoms are selected from one or more of oxygen, nitrogen, and sulfur. R1 is selected from substituted or unsubstituted phosphoxy, substituted or unsubstituted silyl, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C3-C36 heteroaryl, wherein the heteroatom is selected from one or more of oxygen, nitrogen, sulfur, silicon, and selenium.

[0016] In one embodiment of the invention, R1 is selected from the following structures, substituted or unsubstituted:

[0017] ; Any point can be a connection point.

[0018] In this invention, the term "substituted or unsubstituted" means that a group may not be substituted, or may be substituted by one or more substituents. "Substitution" means that a hydrogen atom bonded to a carbon atom of the compound becomes another substituent, and there is no restriction on the position of substitution, as long as the position is where the hydrogen atom is substituted, i.e., the position where the substituent can be substituted. When two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0019] Furthermore, in the term "substituted or unsubstituted", the substituent is selected from deuterium, fluorine, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C3-C20 cycloalkyl, C3-C20 heterocyclic alkyl, deuterated C3-C20 cycloalkyl, and deuterated C3-C20 heterocyclic alkyl, and the heteroatom is selected from one or more of oxygen, nitrogen, and sulfur.

[0020] In one embodiment of the present invention, the hydrogen atoms in Formula 1 can be independently substituted with or not substituted with deuterium.

[0021] In one embodiment of the present invention, the main material is selected from any one of the following structures, but is not limited thereto:

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033] ; Where D represents deuterium.

[0034] The second technical objective of this invention is to provide an organic electroluminescent material containing two hosts, wherein the organic electroluminescent material containing two hosts includes a first host material and a second host material, the first host material being a compound having the structure shown in general formula one, and the second host material having the structure shown in general formula two. ; in, L3, L4, and L5 are each independently selected from a linking bond, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C20 heteroaryl group, and the heteroatom is selected from one or more of oxygen, nitrogen, and sulfur. T1, T2, and T3 are each independently selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted phosphoxy, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, substituted or unsubstituted C6-C42 aryl, and substituted or unsubstituted C3-C42 heteroaryl, wherein the heteroatom is selected from one or more of oxygen, nitrogen, sulfur, silicon, and selenium.

[0035] In one embodiment of the present invention, L3, L4, and L5 are each independently selected from a linking bond, a substituted or unsubstituted C6-C18 aryl group, or a substituted or unsubstituted C3-C12 heteroaryl group, wherein the heteroatom is selected from one or more of oxygen, nitrogen, and sulfur. T1, T2, and T3 are each independently selected from substituted or unsubstituted phosphoxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted germanyl groups, substituted or unsubstituted C6-C36 aryl groups, and substituted or unsubstituted C3-C36 heteroaryl groups, wherein the heteroatoms are selected from one or more of oxygen, nitrogen, sulfur, silicon, and selenium.

[0036] In this invention, the term "substituted or unsubstituted" means that a group may not be substituted, or may be substituted by one or more substituents. "Substitution" means that the hydrogen atom bonded to the carbon atom of the compound becomes another substituent, and there is no restriction on the position of substitution, as long as the position is where the hydrogen atom is substituted, i.e., the position where the substituent can be substituted. When two or more substituents are substituted, the two or more substituents may be the same as or different from each other.

[0037] In one embodiment of the present invention, the second host material is selected from any of the following compounds, but is not limited to the following structures:

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046] .

[0047] Where D represents deuterium.

[0048] In one embodiment of the present invention, the mass ratio of the first main material and the second main material is (1~99):(1~99), for example, 1:99, 1:95, 1:90, 1:85, 1:83, 1:80, 1:75, 2:98, 5:95, 8:92, 10:90, 15:85, 20:80, 25:75, 30:70, 35:65, 38:62, 40:60, 45:55, 50:50, 55:45, 58:42, 60:40, 65:35, 70:30, 75:25, 80:20, 85:15, 88:12, 90:10, 95:5, 98:2, or 99:1, etc.

[0049] The third technical objective of this invention is to provide a method for preparing the above-mentioned organic electroluminescent material containing two main bodies, the synthetic route of which is as follows: I. Preparation of Formula 1:

[0050] Using HTa as an example: (1) Under nitrogen protection, reactant 1 (1 eq), reactant 2 (1 eq), potassium carbonate (2-3 eq) were weighed and added to the reaction system. Toluene, ethanol, water (volume ratio 2:1:1) and catalyst tetra(triphenylphosphine)palladium (0.01-0.05 eq) were added. The reaction was carried out at 40-50℃ for 24 h under nitrogen protection. After the reaction was completed, the mixture was cooled to 25℃, extracted with water, and the organic phase was collected. The organic phase was dried with anhydrous magnesium sulfate and evaporated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / hexane as eluent to obtain the compound HTa-1 shown. (2) Under nitrogen protection, reactant 3 (1 eq), reactant 4 (1 eq), sodium tert-butoxide (2-3 eq) were weighed and added to the reaction system. Dry toluene, catalyst tris(dibenzylacetone) bispalladium (0.02-0.04 eq) and 50% tri-tert-butylphosphine (0.04-0.08 eq) were added. The reaction was carried out at 60-70℃ for 24 h under nitrogen protection. After the reaction was completed, the mixture was cooled to 25℃, extracted with water, and the organic phase was collected. The organic phase was dried with anhydrous magnesium sulfate and evaporated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / hexane as eluent to obtain the compound HTa-2 shown. (3) Under nitrogen protection, weigh HTa-2 (1 eq), reactant 5 (1 eq), sodium tert-butoxide (2-3 eq) and add them to the reaction system. Add dry toluene, catalyst tris(dibenzylacetone) bispalladium (0.02-0.04 eq) and 50% tri-tert-butylphosphine (0.04-0.08 eq). Reflux at 110-120℃ for 24 h under nitrogen protection. After the reaction is completed, cool to 25℃, extract with water and separate the liquid. Collect the organic phase, add anhydrous magnesium sulfate to dry the organic phase, and rotary evaporate under reduced pressure to obtain the crude product. Use dichloromethane / hexane as eluent to purify the crude product by silica gel column chromatography to obtain the compound HTa-3 shown. (4) Under nitrogen protection, weigh HTa-1 (1 eq), HTa-3 (1 eq), and potassium carbonate (2-3 eq) and add them to the reaction system. Add toluene, ethanol, water (2:1:1) and catalyst tetra(triphenylphosphine)palladium (0.01-0.05 eq). Reflux at 80-90℃ for 24 h under nitrogen protection. After the reaction is completed, cool to 25℃, add water to extract and separate the liquid. Collect the organic phase, add anhydrous magnesium sulfate to dry the organic phase, and evaporate under reduced pressure to obtain the crude product. Use dichloromethane / hexane as eluent to purify the crude product by silica gel column chromatography to obtain the compound HTa shown.

[0051] Similarly, HTb can also be prepared using the above method.

[0052] II. Preparation of General Formula II: The reaction route is as follows:

[0053] (1) Under nitrogen protection, reactant 1 (1 eq), reactant 2 (1 eq), and potassium carbonate (2-3 eq) were weighed and added to the reaction system. Toluene, ethanol, water (2:1:1) and catalyst tetra(triphenylphosphine)palladium (0.01-0.05 eq) were added. The reaction was carried out at 40°C for 24 h under nitrogen protection. After the reaction was completed, the mixture was cooled to 25°C, extracted with water, and the organic phase was collected. The organic phase was dried with anhydrous magnesium sulfate and evaporated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / hexane as the eluent to obtain the compound H2-T-1 shown. (2) Under nitrogen protection, weigh H2-T-1 (1 eq), reactant 3 (1 eq), and potassium carbonate (2-3 eq) into the reaction system, add toluene, ethanol, water and catalyst tetra(triphenylphosphine)palladium (0.01-0.05 eq), react at 60°C for 24 h under nitrogen protection, after which cool to 25°C, extract with water and separate the liquid, collect the organic phase, dry the organic phase with anhydrous magnesium sulfate, and evaporate under reduced pressure to obtain crude product; use dichloromethane / hexane as eluent to purify the crude product by silica gel column chromatography to obtain compound H2-T-2 as shown; (3) Under nitrogen protection, weigh H2-T-2 (1 eq), reactant 4 (1 eq), potassium carbonate (2-3 eq) and add them to the reaction system. Add toluene, ethanol, water and catalyst tetra(triphenylphosphine)palladium (0.01-0.05 eq). Reflux at 90°C for 24 h under nitrogen protection. After the reaction is completed, cool to 25°C, add water to extract and separate the liquid. Collect the organic phase, add anhydrous magnesium sulfate to dry the organic phase, and rotary evaporate under reduced pressure to obtain the crude product. Use dichloromethane / hexane as eluent to purify the crude product by silica gel column chromatography to obtain the compound H2-T shown.

[0054] The third technical objective of this invention is to provide an application of an organic electroluminescent material containing two main bodies in the fabrication of organic electroluminescent devices.

[0055] Specifically, the organic electroluminescent device includes a first electrode, a second electrode, and an organic electroluminescent material layer disposed between the first electrode and the second electrode; and the organic electroluminescent material layer includes a light-emitting layer; the light-emitting layer includes a doped material and an organic electroluminescent material containing a dual host as described above.

[0056] Preferably, in the organic electroluminescent material containing two main bodies, the mass ratio of the first main body material, the second main body material, and the dopant material is (1~99):(1~99):(99~1), more preferably (1~20):(1~20):(9~1), and even more preferably 10:10:1.

[0057] Examples include 1:1:99, 1:2:5, 2:2:1, 3:1:1, 5:1:9, 8:2:9, 10:10:1, 20:10:1, 30:10:1, 30:10:10, 40:20:1, 40:50:2, 50:10:1, 60:10:1, 45:45:10, 70:20:10, 80:10:10, 90:10:1, 99:1:1, 1:99:10, 1:10:99, 1:50:1, 1:70:20, 1:90:10, 1:20:99, etc.

[0058] More specifically, the organic electroluminescent device includes an anode, a hole transport region, an emissive layer, an electron transport region, and a cathode; the emissive layer includes a first host material as shown in Formula 1 and a second host material as shown in Formula 2.

[0059] As an anode material, a material with a high work function is generally preferred to facilitate hole injection into the organic material layer. The anode materials that can be used for the first electrode of the organic electroluminescent device of the present invention include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0060] As a cathode material, materials with a small work function are generally preferred to facilitate electron injection into the organic material layer. The cathode materials that can be used for the second electrode of the organic electroluminescent device of the present invention include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials, such as LiF / Al or LiO2 / Al; and so on, but are not limited thereto.

[0061] The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, and a hole blocking layer, with the light-emitting layer located between the electron blocking layer and the hole blocking layer.

[0062] The hole injection layer material is a material that receives holes from the anode at low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.

[0063] Hole injection materials include metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, and conductive polymers based on polyaniline and polythiophene.

[0064] Hole transport layer materials are materials that can receive holes from the anode or hole injection layer and transport the holes to the light-emitting layer, and have high hole mobility; and hole transport layer materials include, but are not limited to, arylamine-based organic materials, conductive polymers, block copolymers that have both conjugated and non-conjugated parts.

[0065] An electron blocking layer can be disposed between the hole transport layer and the light-emitting layer. Materials known in the art, such as arylamine-based organic materials, can be used as the electron blocking layer.

[0066] The main material of the light-emitting layer is selected from the structure of this invention.

[0067] The hole blocking layer can be disposed between the electron transport layer and the light-emitting layer, and can be made of materials known in the art, such as triazine-based compounds.

[0068] The electron transport layer facilitates electron transport. Electron transport materials are those that advantageously receive electrons from the cathode and transport them to the light-emitting layer, exhibiting high electron mobility. These include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavonoid-metal complexes, etc. The thickness of the electron transport layer can range from 1 nm to 50 nm. Electron transport layers with a thickness of 1 nm or greater have the advantage of preventing a decrease in electron transport properties, while thicknesses of 50 nm or less have the advantage of preventing an increase in driving voltage caused by an excessively thick electron transport layer.

[0069] The electron injection layer can promote electron injection, and the electron injection material preferably has the ability to transport electrons, exhibiting an electron injection effect from the cathode, and demonstrating excellent electron injection effect on the light-emitting layer or light-emitting material. It prevents excitons generated in the light-emitting layer from migrating to the hole injection layer, and also possesses excellent thin film forming ability. Specific examples include fluorenones, anthraquinone dimethane, biphenylquinone, thiamethane dioxide, azoles, diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal complexes, nitrogen-containing five-membered ring derivatives, etc., but are not limited to these.

[0070] Depending on the materials used, the above-mentioned organic electroluminescent devices can be top-emitting, bottom-emitting, or bilaterally emitting.

[0071] Furthermore, the organic electroluminescent device described in this invention can be used in organic solar cells, electronic paper, organic photoreceptors, or organic thin-film transistors.

[0072] As can be seen from the above technical solution, compared with the prior art, the present invention has the following beneficial effects: The main material of this invention contains a triarylamine structure, which has the following advantages: 1) Improve hole transport performance: Triarylamines have low ionization potential of amine units, good electron donation, and high hole mobility.

[0073] 2) Improve luminous efficiency: As a light-emitting layer material, it can effectively reduce the total reflection loss and waveguide loss of traditional OLED devices, thereby improving luminous efficiency.

[0074] 3) Extended service life: The triarylamine structure of the compound has good physical and thermal stability, making it difficult for molecules to crystallize and aggregate, thus effectively extending the service life.

[0075] 4) Energy level matching advantage: The introduction of triarylamine structure can adjust the HOMO / LUMO energy levels of the material, making it more compatible with the energy levels of other materials.

[0076] 5) Reduce driving voltage: This helps to improve and balance the transport of charge carriers in the device and reduce the voltage of the device.

[0077] The main material of this invention also contains dibenzofuran naphthalene, which has the following advantages: 1) High fluorescence quantum yield: The dibenzofuran-naphthalene structure usually has a good conjugated system, which can effectively absorb and emit photons, exhibiting a high fluorescence quantum yield. This means that the material can efficiently convert electrical energy into light energy, improving the luminous efficiency of organic electroluminescent devices (OLEDs).

[0078] 2) Good thermal stability: Its molecular structure is relatively stable and has a high thermal decomposition temperature. It can withstand certain temperature changes during device fabrication and use without decomposition or performance degradation, which is beneficial to improving the long-term stability and lifespan of OLEDs.

[0079] 3) Appropriate energy level structure: The HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) energy levels of dibenzofuran-naphthalene can be adjusted through molecular design to make them well matched with the energy levels of other functional layers in OLED, which is beneficial for charge injection and transport, reduces the driving voltage of the device, and improves the performance of the device.

[0080] 4) High structural modifiability: By introducing different substituents into the molecular structure of dibenzofuran-naphthalene, its optical and electrical properties can be controlled to meet different application requirements, such as adjusting the emission color and improving charge transport performance.

[0081] The second body material of the present invention contains a triazine structure, which has the following advantages: 1) Improved stability and electronic tolerance: The triazine structure gives the compound good stability and electronic tolerance, ensuring the material's performance is stable in the working environment and reducing performance degradation caused by external factors and electronic shocks.

[0082] 2) Enhanced electron injection and transport capabilities: This structure has strong electron-withdrawing properties, which can reduce the electron injection energy barrier, making it easier for electrons to be injected into organic materials, while increasing the migration speed of electrons in the material and improving electron transport efficiency.

[0083] 3) Reduced driving voltage: Triazine structure materials applied to organic electroluminescent devices can significantly reduce device driving voltage, reduce energy consumption, and improve energy utilization efficiency.

[0084] 4) Improve luminescence performance: Triazine compounds have good luminescence performance and can be used to prepare organic electroluminescent devices. They can improve the current efficiency of the devices and enable the devices to achieve higher brightness with lower current.

[0085] 5) Extend device lifespan: Triazine-based materials can improve device stability and efficiency, reduce device damage and aging during operation, and effectively extend device lifespan.

[0086] 6) Improved thermal stability: Compounds with triazine structure as the core and aryl and other groups forming side chains have good thermal stability, which can ensure that the device works stably under different temperature environments.

[0087] 7) Improved film-forming properties: Some triazine compounds have improved molecular planarity through design, which enhances the film-forming properties of the material, reduces problems in the production process, and facilitates large-scale production and preparation of high-quality thin-film devices.

[0088] In summary, the organic electroluminescent material with dual host provided by this invention, when used in organic electroluminescent devices, can reduce the driving voltage of the organic electroluminescent devices while improving the efficiency and lifespan of the devices. Attached Figure Description

[0089] Figure 1 The nuclear magnetic resonance hydrogen spectrum of compound H001 prepared in Example 1. Detailed Implementation

[0090] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0091] 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.

[0092] Example 1 Preparation of compound H001

[0093] (1) Under nitrogen protection, reactant 1 (1 eq) (CAS: 13922-41-3), reactant 2 (1 eq) (CAS: 2568850-17-7), potassium carbonate (2.5 eq) were weighed and added to the reaction system. Toluene, ethanol and water in a volume ratio of 2:1:1 and catalyst tetra(triphenylphosphine)palladium (0.01 eq) were added. The reaction was carried out at 40°C for 24 h under nitrogen protection. After the reactants were completely reacted, the heating was stopped and the mixture was cooled to 25°C. Water was added for extraction and separation. The organic phase was collected and dried with anhydrous magnesium sulfate. The crude product was obtained by rotary evaporation under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / hexane as the eluent to obtain compound H001-1 (yield: 59.22%).

[0094] (2) Under nitrogen protection, compound H001-1 (1 eq), reactant 3 (1 eq) (CAS: 1290039-85-8), sodium tert-butoxide (2 eq) were weighed and added to the reaction system. Dry toluene, catalyst tris(dibenzylacetone) bispalladium (0.02 eq) and 50% tri-tert-butylphosphine (0.04 eq) were added. The mixture was refluxed at 120 °C for 24 h under nitrogen protection. After the reaction of the raw materials was completed, the heating was stopped and the mixture was cooled to 25 °C. Water was added for extraction and separation. The organic phase was collected and dried with anhydrous magnesium sulfate. The crude product was obtained by rotary evaporation under reduced pressure. The crude product was purified by silica gel column chromatography using dichloromethane / hexane as the eluent to obtain compound H001 (yield: 65.73%).

[0095] Characterization: HPLC: 99.88%; Test value ((ESI, m / Z): [M+H]+): 627.46; Elemental analysis results: C: 87.95; H: 4.68; N: 2.31; O: 5.19; The proton NMR spectrum is as follows: Figure 1 As shown.

[0096] Example 2 Preparation of compound H2-1

[0097] Under nitrogen protection, reactant 1 (1 eq, CAS: 2681303-14-8), reactant 2 (1 eq, CAS: 1883265-32-4), and potassium carbonate (2.5 eq) were weighed and added to the reaction system. Toluene, ethanol, and water in a volume ratio of 2:1:1 and catalyst tetrakis(triphenylphosphine)palladium (0.02 eq) were added. The mixture was refluxed at 90 °C for 24 h under nitrogen protection. After the reaction was completed, the mixture was cooled to 25 °C, extracted with water, and the organic phase was collected. The organic phase was dried with anhydrous magnesium sulfate and evaporated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using dichloromethane / hexane as the eluent to obtain compound H2-1 (yield: 66.87%).

[0098] Performance characterization: HPLC: 99.90%; Measured value ((ESI, m / Z): [M+H]+): 549.34; Elemental analysis results: C: 85.14; H: 4.33; N: 7.80; O: 3.03; In addition, it should be noted that other compounds of the present invention can be obtained by referring to the synthesis methods of the examples listed above, so they will not be listed one by one here.

[0099] Device Example 1 Fabrication of organic electroluminescent devices: ITO anodizing: The coating thickness is 1500 mm. The ITO (indium tin oxide)-Ag-ITO (indium tin oxide) glass substrate was cleaned twice with distilled water, ultrasonically washed for 30 minutes, then repeatedly cleaned twice with distilled water, ultrasonically washed for 10 minutes. After washing, it was ultrasonically washed sequentially with methanol, acetone and isopropanol (5 minutes each time), dried, and then transferred to a plasma cleaner for 5 minutes to obtain the ITO anode.

[0100] HIL (Hole Injection Layer): In a vapor deposition machine, 200 Å of 4,4',4''-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA) is vacuum-deposited onto an ITO anode to form a hole injection layer.

[0101] HTL (Hole Transport Layer): A hole transport layer is formed by vacuum evaporating NPB (i.e., N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine) at 400 Å onto the hole injection layer.

[0102] Emitting layer: The emitting layer comprises a first host material, a second host material, and a guest dopant. After forming a hole injection layer and a hole transport layer, the emitting layer is formed on the HTL: the first host compound and the second host compound are introduced as hosts into two chambers of a vacuum vapor deposition apparatus, and compound Z1 is introduced as a dopant into another chamber; the two host materials are evaporated at a 1:1 ratio, and the dopant material is evaporated simultaneously at different rates, and a doping amount of 3wt% based on the total amount of host and dopant is deposited to form an emitting layer with a thickness of 40nm on the hole transport layer.

[0103] HBL (Hole Blocking Layer): A hole blocking layer is formed by vacuum evaporation of bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq) at 100 Åm on the luminescent layer.

[0104] ETL (Electron Transport Layer): 400 Å of 8-hydroxyquinoline aluminum (Alq3) is vacuum-deposited onto the hole-blocking layer to form the electron transport layer.

[0105] EIL (Electron Injection Layer): LiF 210Å is vacuum-deposited on the electron transport layer to form the electron injection layer.

[0106] Cathode: Magnesium and silver are deposited at a deposition rate of 1 Å / s, with a deposition rate ratio of 1:9, to form a cathode, thus obtaining an organic electroluminescent device.

[0107] Referring to the organic electroluminescent device and its preparation method provided in Device Example 1, another 50 organic electroluminescent compounds were selected to replace the first host compound and the second host compound for the vapor deposition of the host material, and organic electroluminescent devices of the corresponding compounds were prepared.

[0108] Red-light doped material (Z1) .

[0109] Device Examples 1-50, Comparative Examples 1-8 and Parallel Examples 1-9 The device fabrication processes of Device Examples 1-50, Comparative Examples 1-8 and Parallel Examples 1-9 are exactly the same, and the same substrate material and electrode material are used. The film thickness of the electrode material is also consistent. The difference is that the two main materials are different. The corresponding first main compound (first main material) and second main compound (second main material) in Table 1 are selected respectively. The specific parameters are shown in Table 1.

[0110] Table 1. Materials used in Device Examples 1-50, Comparative Examples 1-8 and Parallel Examples 1-9

[0111]

[0112] The comparative example structure is shown below:

[0113] Performance testing: The driving voltage, luminous efficiency, and lifetime of the organic electroluminescent devices obtained in Comparative Examples 1-8, Parallel Examples 1-9, and Device Examples 1-50 were characterized at a brightness of 7000 nits. The test results are shown in Table 2 below.

[0114] Table 2. Test results of devices 1-50, comparative examples 1-8, and parallel examples 1-9

[0115]

[0116]

[0117] As can be seen from Table 2, the driving voltage of the organic electroluminescent devices provided by Device Examples 1-50 of the present invention is 2.72V~3.05V, which is significantly lower than that of Comparative Examples 1-8, and is reduced by 13.35%-25.47% compared with the comparative examples. At the same time, the luminous efficiency is higher than that of Comparative Examples 1-8, which is increased by 30.64%-79.72% compared with the comparative examples. Moreover, the lifetime is significantly improved compared with Comparative Examples 1-8, which is increased by 14.43%-18.92% compared with the comparative examples.

[0118] Therefore, it can be seen that, compared with organic electroluminescent devices prepared using the organic electroluminescent material with dual host provided by the present invention as the light-emitting layer, the driving voltage of the light-emitting device of the present invention is significantly reduced, and the luminous efficiency and lifetime are significantly improved.

[0119] The main reason for this is that in the dual-body material of the present invention, the triazine structure has good stability, which can increase the device lifespan. At the same time, the triazine structure has strong electron accepting ability, which can reduce the energy required for electron injection and reduce the voltage required for device operation. The triarylamine structure has good film-forming properties, which can improve the performance and stability of the device. At the same time, the triarylamine structure has strong electron donating ability, which can improve electron transport efficiency.

[0120] The applicant declares that the present invention is illustrated through the above embodiments to demonstrate the main material, the organic electroluminescent material containing two main components, and its applications. However, the present invention is not limited to the above process steps, that is, it does not mean that the present invention must rely on the above process steps to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials used in the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A main material, characterized in that, The main material is a compound having the structure shown in Formula 1: in, L0 and L1 are connecting bonds, substituted or unsubstituted C6-C30 aromatic amino groups, substituted or unsubstituted C3-C30 heteroaromatic amino groups, substituted or unsubstituted C6-C30 aryl groups, and substituted or unsubstituted C3-C30 heteroaromatic groups, with the heteroatom selected from one or more of oxygen, nitrogen, and sulfur. Ar is selected from the following structures: ； * Represents a linking site; A is selected from substituted or unsubstituted benzene or naphthalene; R1 is selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted phosphoroxy, substituted or unsubstituted silyl, substituted or unsubstituted C6-C42 aryl, substituted or unsubstituted C3-C42 heteroaryl, wherein the heteroatom is selected from one or more of oxygen, nitrogen, sulfur, silicon, and selenium. R2 is selected from the following groups: ； Any point can be a connection point; The substituents in "substituted or unsubstituted" are selected from deuterium, fluorine, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C3-C20 cycloalkyl, C3-C20 heterocyclic alkyl, deuterated C3-C20 cycloalkyl, and deuterated C3-C20 heterocyclic alkyl, and the heteroatoms are selected from one or more of oxygen, nitrogen, and sulfur.

2. The main material according to claim 1, characterized in that, The main material has the following two structures: ； Wherein, L0 and L1 are connecting bonds, substituted or unsubstituted C6-C18 aromatic amino groups, substituted or unsubstituted C3-C18 heteroaromatic amino groups, substituted or unsubstituted C6-C18 aryl groups, and substituted or unsubstituted C3-C18 heteroaromatic groups, and their heteroatoms are selected from one or more of oxygen, nitrogen, and sulfur. R1 is selected from substituted or unsubstituted phosphoxy, substituted or unsubstituted silyl, substituted or unsubstituted C6-C36 aryl, substituted or unsubstituted C3-C36 heteroaryl, wherein the heteroatom is selected from one or more of oxygen, nitrogen, sulfur, silicon, and selenium.

3. The main material according to claim 1, characterized in that, R1 is selected from the following structures, whether substituted or unsubstituted: ； Any point can be a connection point.

4. The main material according to claim 1, characterized in that, In Formula I, all hydrogen atoms can be independently substituted with or not substituted with deuterium.

5. The main material according to claim 1, characterized in that, The main material is selected from any of the following structures: ； Where D represents deuterium.

6. An organic electroluminescent material containing two main components, characterized in that, The organic electroluminescent material containing two hosts comprises a first host material and a second host material, wherein the first host material is the host material described in any one of claims 1 to 5, and the second host material has the structure shown in general formula 2: ； Among them, L3, L4, and L5 are each independently selected from the linking bond, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C20 heteroaryl, and their heteroatoms are selected from one or more of oxygen, nitrogen, and sulfur; T1, T2, and T3 are each independently selected from hydrogen, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted phosphoxy, substituted or unsubstituted silyl, substituted or unsubstituted germanyl, substituted or unsubstituted C6-C42 aryl, and substituted or unsubstituted C3-C42 heteroaryl, wherein the heteroatom is selected from one or more of oxygen, nitrogen, sulfur, silicon, and selenium; Preferably, the mass ratio of the first main material and the second main material is (1~99):(1~99).

7. The organic electroluminescent material containing two main bodies according to claim 6, characterized in that, L3, L4, and L5 are each independently selected from the linking bond, substituted or unsubstituted C6-C18 aryl, substituted or unsubstituted C3-C12 heteroaryl, and their heteroatoms are selected from one or more of oxygen, nitrogen, and sulfur; T1, T2, and T3 are each independently selected from substituted or unsubstituted phosphoxy groups, substituted or unsubstituted silyl groups, substituted or unsubstituted germanyl groups, substituted or unsubstituted C6-C36 aryl groups, and substituted or unsubstituted C3-C36 heteroaryl groups, wherein the heteroatoms are selected from one or more of oxygen, nitrogen, sulfur, silicon, and selenium.

8. The organic electroluminescent material containing two main bodies according to claim 6, characterized in that, In the term "substituted or unsubstituted", the substituent is selected from deuterium, fluorine, cyano, C1-C10 alkyl, deuterated C1-C10 alkyl, C3-C20 cycloalkyl, C3-C20 heterocyclic alkyl, deuterated C3-C20 cycloalkyl, and deuterated C3-C20 heterocyclic alkyl, and the heteroatom is selected from one or more of oxygen, nitrogen, and sulfur.

9. The organic electroluminescent material containing two main bodies according to claim 6, characterized in that, The second host material is selected from any one of the following compounds: 。 Where D represents deuterium.

10. An organic electroluminescent device, characterized in that, The organic electroluminescent device includes a first electrode, a second electrode, and an organic electroluminescent material layer disposed between the first electrode and the second electrode; and the organic electroluminescent material layer includes a light-emitting layer; the light-emitting layer includes a doped material and the organic electroluminescent material containing a dual host as described in any one of claims 6-9.

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