Host material, organic electroluminescent material containing double hosts and application

Abstract

The invention belongs to the field of organic electroluminescent materials, and discloses a host material, an organic electroluminescent material containing double hosts and application. The double-host-containing organic electroluminescent material comprises a first host material and a second host material, the first host material is a compound having a structure represented by a general formula I, and the second host material is a compound having a structure represented by a general formula II. According to the organic electroluminescent device, triplet excitons are dispersed on two main bodies by using a double-main-body material, triplet-triplet annihilation is reduced, the driving voltage of the organic electroluminescent device is reduced, the luminous efficiency of the device can be improved, and the service life of the device can be prolonged.

Description

Technical Field

[0001] The present invention belongs to the field of organic electroluminescent materials, and particularly relates to a host material, an organic electroluminescent material containing a double host, and applications thereof. Background Art

[0002] Organic Light Emitting Diode (OLED) technology is an electroluminescent technology that uses organic materials as the light-emitting layer. This technology has the advantages of low driving voltage, high brightness, high efficiency, and the ability to achieve large-area flat-panel color display. The principle of organic electroluminescence is based on the fact that when a voltage is applied to the 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. The excitons release energy during the relaxation process, generating photons, thereby achieving light emission. In recent years, significant progress has been made in the research of organic electroluminescent technology, including improving the efficiency, lifespan, and brightness of devices, reducing costs, and achieving a wider color gamut. These advancements have made organic electroluminescent technology have broad application prospects in the fields of display and lighting.

[0003] The efficiency of Organic Light Emitting Diode (OLED) usually refers to the ability of the device to convert electrical energy into light energy, which is mainly divided into internal quantum efficiency and external quantum efficiency. The internal quantum efficiency refers to the recombination luminescence efficiency of excitons in the light-emitting layer, while the 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] Currently, the technical problems of organic electroluminescent devices mainly include the following aspects:

[0005] (1) Efficiency problem: The luminous efficiency of organic electroluminescent devices is relatively low and needs to be further improved. (2) Lifespan problem: The stability and durability of organic materials are poor, resulting in a short lifespan of the devices. (3) Color stability problem: The color of organic materials is easily affected by environmental factors such as temperature and humidity, resulting in unstable color. (4) Manufacturing process problem: The manufacturing process of organic electroluminescent devices is relatively complex and needs to be further optimized. (5) Cost problem: The costs of organic materials and manufacturing processes are relatively high, restricting the large-scale application of organic electroluminescent devices.

[0006] Improving the efficiency of OLED is achieved through host-guest doping in the light-emitting layer. This is because the radiative transition of triplet excitons of most organic molecules is forbidden and makes little contribution to electroluminescence. By doping with organometallic complexes such as platinum, iridium, and osmium, the triplet excitons of organic molecules can be transferred to the triplet state of the metal complex, thereby greatly improving the efficiency of organic light-emitting devices. However, triplet-triplet annihilation (TTA) occurs during the transfer process of triplet excitons, resulting in energy loss and causing efficiency roll-off in organic light-emitting devices.

[0007] Therefore, how to develop an organic electroluminescent material containing a dual host, a preparation method and an organic electroluminescent device with long life and low driving voltage is a technical problem that those skilled in the art urgently need to solve. Summary of the Invention

[0008] In view of this, aiming at the deficiencies of the prior art, the present invention discloses and provides a host material, an organic electroluminescent material containing a dual host, a preparation method and an application. Applying the organic electroluminescent material containing a dual host of the present invention to a specific light-emitting device has low driving voltage, high luminous efficiency and long service life.

[0009] It should be noted that for the organic electroluminescent device with a dual host provided by the present invention, by using this dual host material, triplet excitons can be dispersed on two hosts, which can reduce triplet-triplet annihilation (TTA). While reducing the driving voltage of the organic electroluminescent device, it can also improve the efficiency and life of the device.

[0010] Among them, the structure with a triarylamine usually has good stability, which can effectively extend the service life of the organic electroluminescent device. The triarylamine structure has strong electron-donating ability and can effectively transport holes. This helps to improve the hole injection efficiency, enable holes to be injected from the anode into the light-emitting layer more smoothly, promote the efficient recombination of electrons and holes in the light-emitting layer, and thus improve the luminous efficiency of the organic electroluminescent device. Moreover, some triarylamine structure compounds have good rigidity and film-forming properties, which are beneficial to forming a uniform and stable thin film during the device preparation process, improving the performance and stability of the device.

[0011] The structure with a triazine has strong electron-accepting ability and can effectively transport electrons. The triazine structure can reduce the energy required for electron injection, enabling the organic electroluminescent device to be driven at a lower voltage, reducing the energy consumption of the device, and at the same time being beneficial to extending the service life of the device. The triazine structure usually has high thermal stability and chemical stability. This can enable the organic electroluminescent device to maintain good performance stability under different working environments, reducing the attenuation of device performance caused by environmental factors. By chemically modifying the triazine structure or combining it with other functional groups, the emission color of the organic electroluminescent device can be adjusted to a certain extent, realizing fine control of the emission spectrum of the device to meet the color display requirements of different application scenarios.

[0012] In order to achieve the above object, the following technical solutions are adopted:

[0013] The first technical object of the present invention is to provide a host material, and the structure of the host material is shown in General Formula I:

[0014]

[0015] Among them,

[0016] A 1 and A 2 are each independently selected from substituted or unsubstituted (C6-C42) aryl, substituted or unsubstituted (C3-C42) heteroaryl;

[0017] D is an intermediate of the first host, and its structure is:

[0018]

[0019] * represents a substitutable site.

[0020] Furthermore, A 1 and A 2 are each independently selected from substituted or unsubstituted (C6-C36) aryl, substituted or unsubstituted (C3-C36) heteroaryl.

[0021] Even further, A 1 and A 2 are each independently selected from substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C3-C30) heteroaryl.

[0022] Optionally, the heteroaryl includes a monocyclic aromatic group and a polycyclic aromatic ring system having at least one heteroatom, and the heteroatom includes but is not limited to O, S, N.

[0023] In the technical solution of the present invention, the general formula I has the following structure, but is not limited to the following structure:

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037] The second technical object of the present invention is to provide an organic electroluminescent material containing a double host. The organic electroluminescent material containing a double host includes a first host material and a second host material. The first host material is the above-mentioned host material, and the second host material has a structure shown in General Formula II:

[0038]

[0039] Wherein,

[0040] A 3 、A 4 、A 5 are each independently selected from a substituted or unsubstituted (C6-C42) aryl group or a substituted or unsubstituted (C3-C42) heteroaryl group.

[0041] Further, A 3 、A 4 、A 5 are each independently selected from a substituted or unsubstituted (C6-C36) aryl group or a substituted or unsubstituted (C3-C36) heteroaryl group.

[0042] Furthermore, A 3 、A 4 、A 5 are each independently selected from a substituted or unsubstituted (C6-C30) aryl group or a substituted or unsubstituted (C3-C30) heteroaryl group.

[0043] Optionally, the heteroaryl group includes a monocyclic aromatic group and a polycyclic aromatic ring system containing at least one heteroatom. The heteroatom includes, but is not limited to, O, S, and N.

[0044] In the above technical solution, the "substituted or unsubstituted" means that the group may not be substituted or may be substituted by one or more substituents. The "substitution" means that a hydrogen atom bonded to a carbon atom of the compound becomes another substituent, and the substitution position is not limited as long as it is the position where the hydrogen atom is substituted, that is, the position where the substituent can be substituted. When two or more substituents are substituted, the two or more substituents may be the same or different from each other.

[0045] Moreover, in the "substituted or unsubstituted", the substituted group is selected from deuterium, fluorine, C1-C10 alkyl, deuterium-substituted C1-C10 alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, deuterium-substituted C3-C20 cycloalkyl, deuterium-substituted C3-C20 heterocycloalkyl, and its heteroatoms are selected from oxygen, nitrogen, sulfur; the substituted groups in the above-mentioned "substituted or unsubstituted" include but are not limited to the following structures:

[0046]

[0047]

[0048]

[0049] In the technical solution of the present invention, the general formula II is selected from any one of the following compounds, but not limited to the following structures:

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057] The third technical object of the present invention is to provide a preparation method of the above-mentioned organic electroluminescent material containing a double host, and the synthesis route is as follows:

[0058] I. Intermediate The preparation process is as follows:

[0059] 1. Preparation of intermediate D-A:

[0060]

[0061] (1) Under a nitrogen protection system, weigh reactant 1 (1eq), reactant 2 (1eq), and potassium carbonate (1.5-3eq) and put them into the reaction system. Add tetrahydrofuran, water, and the catalyst tetrakis(triphenylphosphine)palladium (0.02-0.10eq). Reflux at 50°C for 24h under nitrogen protection. After the reaction is completed, cool to 25°C, and after treatment, the shown compound D-A-1 is obtained;

[0062] (2) Under a nitrogen protection system, dissolve compound D-A-1 (1 eq) in toluene, then heat up to 100 °C and stir for 3 h. After the reaction is completed, cool to 25 °C and, after treatment, obtain the shown compound D-A-2;

[0063] (3) Under a nitrogen protection system, dissolve iodine bis(pyridine) tetrafluoroborate in dichloromethane, cool down to -78 °C, add HBF 4 Stir for 10 min, filter the solid, keep the filtrate at -60 °C, slowly dropwise add compound D-A-2. After the reaction is completed, after treatment, obtain the shown compound D-A-3;

[0064] (4) Under a nitrogen protection system, dissolve compound D-A-3 (1 eq) in diethyl ether, slowly add AlCl 3 , stir for 15 min and then cool down to 0 °C, stir for 1 h. After the reaction is completed, raise the temperature to room temperature and, after treatment, obtain the shown compound D-A-4;

[0065] (5) Under a nitrogen protection system, dissolve compound D-A-4 (1 eq) in dichloromethane, then heat up to 30 °C and stir. Then dissolve NBS in dichloromethane and add it to the system in three portions. After the reaction is completed, cool to 25 °C and, after treatment, obtain the shown intermediate D-A;

[0066] 2. Preparation of intermediates D-B and D-C:

[0067]

[0068] (1) Under a nitrogen protection system, weigh reactant 1 (1 eq), reactant 2 (1 eq), and potassium carbonate (1.5 - 3 eq) and put them into the reaction system. Add tetrahydrofuran, water, and the catalyst tetrakis(triphenylphosphine)palladium(0) (0.02 - 0.10 eq). Under nitrogen protection, reflux at 50 °C for 24 h. After the reaction is completed, cool to 25 °C and, after treatment, obtain the shown compound D-B-1 / D-C-1;

[0069] (2) Under a nitrogen protection system, dissolve compound D-B-1 / D-C-1 (1 eq) in toluene, then heat up to 100 °C and stir for 3 h. After the reaction is completed, cool to 25 °C and, after treatment, obtain the shown compound D-B-2 / D-C-2;

[0070] (3) Under a nitrogen protection system, dissolve iodine bis(pyridine) tetrafluoroborate in dichloromethane, cool down to -78 °C, add HBF 4 Stir for 10 min, filter the solid, keep the filtrate at -60 °C, slowly dropwise add compound D-B-2 / D-C-2. After the reaction is completed, after treatment, obtain the shown compound D-B-3 / D-C-3;

[0071] (4) Under a nitrogen protection system, dissolve compound D-B-3 / D-C-3 (1 eq) in diethyl ether, and slowly add AlCl 3 , after stirring for 15 min, cool the temperature to 0 °C, stir for 1 h. After the reaction is completed, raise the temperature to room temperature, and after treatment, the shown compound D-B / D-C is obtained;

[0072] II. Preparation of General Formula I:

[0073]

[0074] (1) Under a nitrogen protection system, weigh reactant 1 (1 eq), reactant 2 (1 eq), and potassium carbonate (2 - 4 eq) and put them into the reaction system. Add toluene, ethanol, water, and the catalyst tetrakis(triphenylphosphine)palladium(0) (0.02 - 0.08 eq). Reflux at 90 °C for 24 h under nitrogen protection. After the reaction is completed, then cool to 25 °C, and after treatment, the shown compound H-1 is obtained;

[0075] (2) Under a nitrogen protection system, weigh H-1 (1 eq), reactant 3 (1 eq), and potassium carbonate (2 - 4 eq) and put them into the reaction system. Add toluene, ethanol, water, and the catalyst tetrakis(triphenylphosphine)palladium(0) (0.02 - 0.08 eq). Reflux at 90 °C for 24 h under nitrogen protection. After the reaction is completed, then cool to 25 °C, and after treatment, the shown compound H-2 is obtained;

[0076] (3) Under a nitrogen protection system, weigh intermediate D (1 eq), bis(pinacolato)diboron (1.5 - 2 eq), and potassium acetate (2 - 4 eq) and put them into the reaction system. Add dioxane, the catalyst tris(dibenzylideneacetone)dipalladium(0) (0.02 - 0.04 eq), and X-phos (0.04 - 0.08 eq). Reflux at 100 °C for 24 h under nitrogen protection. After the reaction is completed, then cool to 25 °C, and after treatment, the shown compound H-3 is obtained;

[0077] (4) Under a nitrogen protection system, weigh H-2 (1 eq), H-3 (1 eq), and potassium carbonate (2 - 4 eq) and put them into the reaction system. Add toluene, ethanol, water, and the catalyst tetrakis(triphenylphosphine)palladium(0) (0.02 - 0.08 eq). Reflux at 90 °C for 24 h under nitrogen protection. After the reaction is completed, then cool to 25 °C, and after treatment, the shown General Formula I is obtained.

[0078] III. Preparation of General Formula II:

[0079]

[0080] Under nitrogen protection, reactant 1 (1 eq), reactant 2 (1 eq), sodium tert-butoxide (2-3 eq) were weighed and put into the reaction system, toluene, catalyst tri(dibenzylideneacetone) palladium (0.01-0.04 eq) and tri-tert-butylphosphine (0.022-0.088 eq) were added, and the mixture was refluxed at 110-120°C for 24 h under nitrogen protection. After the reaction was completed, the mixture was cooled to 25°C and treated to obtain the compound of formula 2 shown in the figure.

[0081] The third technical purpose of the present invention is to provide an application of an organic electroluminescent material containing a double host in the preparation of an organic electroluminescent device.

[0082] Specifically, the organic electroluminescent device comprises 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 comprises a light-emitting layer; the light-emitting layer comprises a doping material and the organic electroluminescent material containing a double host as described above;

[0083] Among them, the mass ratio of the first host material, the second host material and the doping material in the dual-host organic electroluminescent material is (1-99):(1-99):(99-1), preferably (1-20):(1-20):(9-1), and more preferably 10:10:1.

[0084] More specifically, the organic electroluminescent device comprises an anode, a hole transport region, a light emitting layer, an electron transport region and a cathode. The light emitting layer comprises a first host material shown in general formula 1 and a second host material shown in general formula 2.

[0085] As the anode material, a material with a large work function is generally preferred so that holes can be smoothly injected 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 SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, but not limited thereto.

[0086] As the cathode material, a material with a small work function is generally preferred so that electrons can be smoothly injected 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 structure materials, such as LiF / Al or LiO 2 / Al; and so on, but not limited to.

[0087] The hole injection layer material is a material that receives holes from the anode at a 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. The hole injection materials include metal porphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and conductive polymers based on polyaniline and polythiophene, etc.

[0088] The hole transport layer material is a material that can receive holes from the anode or the hole injection layer and transport the holes to the light-emitting layer, and has a high hole mobility; and the hole transport layer materials include arylamine-based organic materials, conductive polymers, block copolymers having both a conjugated part and a non-conjugated part, etc., but are not limited thereto.

[0089] An electron blocking layer can be provided between the hole transport layer and the light-emitting layer. As the electron blocking layer, materials known in the art can be used, such as arylamine-based organic materials.

[0090] The host material of the light-emitting layer is selected from the structures of the present invention.

[0091] A hole blocking layer can be provided between the electron transport layer and the light-emitting layer, and materials known in the art can be used, such as triazine-based compounds.

[0092] The electron transport layer can play a role in promoting electron transport. The electron transport material is advantageously a material that receives electrons from the cathode and transports the electrons to the light-emitting layer and has a high electron mobility. It includes: Al complexes of 8-hydroxyquinoline; complexes containing Alq 3 of complexes; organic radical compounds; hydroxyflavone-metal complexes, etc., but are not limited thereto. The thickness of the electron transport layer can be 1 nm to 50 nm. The electron transport layer with a thickness of 1 nm or more has the advantage of preventing the degradation of electron transport characteristics, and the thickness of 50 nm or less has the advantage of preventing the increase in driving voltage caused by the too thick electron transport layer.

[0093] The electron injection layer can play a role in promoting electron injection, and the electron injection material preferably has the ability to transport electrons, has an electron injection effect from the cathode, has an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevents the excitons generated in the light-emitting layer from migrating to the hole injection layer, and in addition, has an excellent thin film forming ability. Specific examples thereof include fluorenone, anthraquinone dimethane, biphenylquinone, thiopyran dioxide, oxazole, dioxazole, triazole, imidazole, perylene tetracarboxylic acid, fluoreneylidene methane, anthrone, etc. and their derivatives, metal complexes, nitrogen-containing five-membered ring derivatives, etc., but are not limited thereto.

[0094] Depending on the materials used, the above-mentioned organic electroluminescent device can be a top-emission type, a bottom-emission type, or a double-sided emission type.

[0095] In addition, the organic electroluminescent device described in the present invention can be used in organic solar cells, electronic papers, organic photoreceptors, or organic thin-film transistors.

[0096] From the above technical solutions, it can be seen that compared with the prior art, the present invention has the following beneficial effects:

[0097] The organic electroluminescent material provided by the present invention is a dual-host organic compound. In the first host, a triazine structure is included, which can improve the electron transport performance, luminous efficiency, and stability of the device, and also reduce the driving voltage and facilitate the adjustment of the emission color; the triarylamine structure in the second host has a strong electron-donating ability and can effectively transport holes, which helps to improve the hole injection efficiency, enabling holes to be more smoothly injected from the anode into the light-emitting layer, promoting the efficient recombination of electrons and holes in the light-emitting layer, and thus improving the luminous efficiency of the organic electroluminescent device; at the same time, the triarylamine structure usually has good stability, which can effectively extend the service life of the organic electroluminescent device, and some triarylamine structure compounds have good rigidity and film-forming properties, which are beneficial to forming a uniform and stable thin film during the device preparation process, improving the performance and stability of the device.

[0098] Based on the above analysis, it can be seen that the dual-host structure in the present invention can reduce triplet-triplet annihilation (TTA) after being used in an organic electroluminescent device, while reducing the driving voltage of the organic electroluminescent device and improving the efficiency and lifespan of the device. Description of the Drawings

[0099] In order to more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the following will briefly introduce the drawings required for the description of the embodiments or the prior art. Obviously, the drawings in the following description are only the embodiments of the present invention. For those of ordinary skill in the art, other drawings can be obtained according to the provided drawings without creative efforts.

[0100] Figure 1 1H NMR spectrum of compound H110.

[0101] Figure 2 1H NMR spectrum of compound Y086. Detailed Embodiments

[0102] The technical solution of the present invention will be clearly and completely described below in conjunction with the embodiments of the present invention and the relevant attached drawings. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. All other embodiments obtained by those of ordinary skill in the art based on the embodiments of the present invention without creative work belong to the scope of protection of the present invention.

[0103] The present invention specifically discloses a main material, an organic electroluminescent material containing a double main body and its application.

[0104] It should be noted that the values given in the following embodiments are as accurate as possible. However, those skilled in the art understand that due to inevitable measurement errors and experimental operation problems, each number should be understood as an approximate number rather than an absolutely accurate value.

[0105] Example 1: Preparation of Intermediate D1

[0106]

[0107] (1) Under a nitrogen protection system, weigh reactant 1 (1 eq) (cas: 68490-58-4), reactant 2 (1 eq) (cas: 1534369-41-9), and potassium carbonate (2.5 eq) into the reaction system, displace nitrogen, add tetrahydrofuran, water, and the catalyst tetrakis(triphenylphosphine)palladium(0) (0.02 eq), displace nitrogen again, reflux at 50 °C for 24 h under nitrogen protection. Stop heating after the raw materials have reacted, cool to 25 °C, add water for extraction and separation, collect the organic phase, dry the organic phase with anhydrous magnesium sulfate, and obtain the crude product by rotary evaporation under reduced pressure; use dichloromethane / hexane as the eluent, and purify the crude product by silica gel column chromatography to obtain D1-1;

[0108] HPLC: 96.7%; Molecular weight: 288.18; Yield: 55.8%;

[0109] (2) Under a nitrogen protection system, dissolve compound D1-1 (1 eq) in toluene, then heat to 100 °C and stir for 3 h. After the reaction is completed, cool to 25 °C. After the raw materials have reacted, filter through a silica gel funnel while it is hot, wash with toluene, and obtain the crude product by rotary evaporation under reduced pressure; use ethyl acetate / hexane as the eluent, and purify the crude product by silica gel column chromatography to obtain D1-2;

[0110] HPLC: 98.8%; Molecular weight: 268.24; Yield: 62.8%;

[0111] (3) Under a nitrogen protection system, dissolve iodine bis(pyridine) tetrafluoroborate (2 eq) in dichloromethane, cool to -78 °C, and add HBF 4(4eq) Stir for 10 min, filter the solid, keep the filtrate at -60 °C, slowly add compound D1-2 (1eq), after the reaction is completed, use dichloromethane / hexane as the eluent, and purify the crude product by silica gel column chromatography to obtain the shown compound D1-3;

[0112] HPLC: 92.5%; Molecular weight: 278.16; Yield: 60.5%;

[0113] (4) Under a nitrogen protection system, dissolve compound D1-3 (1eq) in ether, slowly add AlCl 3 (1.2eq), stir for 15 min and then cool to 0 °C, stir for 1 h, after the reaction is completed, slowly raise the temperature to room temperature, then slowly add ethyl acetate until no bubbles are generated, cool to room temperature, use dichloromethane / hexane as the eluent, and purify the crude product by silica gel column chromatography to obtain D1;

[0114] HPLC: 99.02%; Molecular weight: 264.25; Yield: 54.2%.

[0115] Example 2: Preparation of compound H110

[0116]

[0117] (1) Under a nitrogen protection system, weigh reactant 1 (1eq) (cas: 108-77-0), reactant 2 (1eq) (cas: 98-80-6), and potassium carbonate (2.5eq) into the reaction system, displace nitrogen, add toluene, ethanol, water and the catalyst tetrakis(triphenylphosphine)palladium (0.02eq), displace nitrogen, reflux at 90 °C for 24 h under nitrogen protection; stop heating after the raw materials react completely, cool to 25 °C, add water for extraction and liquid separation, collect the organic phase, dry the organic phase with anhydrous magnesium sulfate, and obtain the crude product by rotary evaporation under reduced pressure; use dichloromethane / hexane as the eluent, and purify the crude product by silica gel column chromatography to obtain H110-1;

[0118] HPLC: 97.56%; Molecular weight: 225.23; Yield 57.6%.

[0119] (2) Under a nitrogen protection system, weigh compound H110-1 (1 eq), reactant 3 (1 eq) (cas: 162607-19-4), and potassium carbonate (2.5 eq) and put them into the reaction system. Replace nitrogen, add toluene, ethanol, water, and the catalyst tetrakis(triphenylphosphine)palladium (0.02 eq). Replace nitrogen again, and reflux at 90 °C for 24 h under nitrogen protection. Stop heating after the raw materials have reacted completely, cool to 25 °C, add water for extraction and separation, collect the organic phase, dry the organic phase with anhydrous magnesium sulfate, and obtain the crude product by rotary evaporation under reduced pressure. Use dichloromethane / hexane as the eluent and purify the crude product by silica gel column chromatography to obtain H110-2;

[0120] HPLC: 98.76%; Molecular weight: 357.96; Yield: 55.2%.

[0121] (3) Under a nitrogen protection system, weigh intermediate D1 (1 eq), bis(pinacolato)diboron (1.5 eq), and potassium acetate (2 eq) and put them into the reaction system. Replace nitrogen, add dioxane, the catalyst tris(dibenzylideneacetone)dipalladium (0.02 eq), and X-phos (0.04 eq). Replace nitrogen again, and reflux at 100 °C for 24 h under nitrogen protection. Stop heating after the raw materials have reacted completely, cool to 25 °C, add water for extraction and separation, collect the organic phase, dry the organic phase with anhydrous magnesium sulfate, and obtain the crude product by rotary evaporation under reduced pressure. Use dichloromethane / hexane as the eluent and purify the crude product by silica gel column chromatography to obtain H110-3;

[0122] HPLC: 98.60%; Molecular weight: 356.21; Yield: 72.5%.

[0123] (4) Under a nitrogen protection system, weigh compound H110-2 (1 eq), compound H110-3 (1 eq), and potassium carbonate (2.5 eq) and put them into the reaction system. Replace nitrogen, add toluene, ethanol, water, and the catalyst tetrakis(triphenylphosphine)palladium (0.02 eq). Replace nitrogen again, and reflux at 90 °C for 24 h under nitrogen protection. Stop heating after the raw materials have reacted completely, cool to 25 °C, add water for extraction and separation, collect the organic phase, dry the organic phase with anhydrous magnesium sulfate, and obtain the crude product by rotary evaporation under reduced pressure. Use dichloromethane / hexane as the eluent and purify the crude product by silica gel column chromatography to obtain H110;

[0124] HPLC: 99.85%; Molecular weight: 551.33; Yield: 52.6%.

[0125] 1HNMR(500MHz,Chloroform-d)δ8.45-8.37(m,2H),8.26(t,J=2.1Hz,1H),8.01-7.93(m,2H),7.83(dd,J=9.2,1.2Hz,1H),7.64(dd,J=6.7,1.5Hz,1H),7.63- 7.57(m,2H),7.55-7.45(m,6H),7.42(dd,J=7.0,1.3Hz,1H),7.37-7.28(m,2H ),7.15(dd,J=7.5,1.3Hz,1H),4.81(d,J=17.9Hz,1H),4.54(d,J=17.9Hz,1H).

[0126] H NMR spectrum: Figure 1 shown.

[0127] Example 3: Preparation of Compound Y086

[0128]

[0129] Under nitrogen protection, reactant 1 (1 eq) (cas: 135-88-6), reactant 2 (1 eq) (cas: 51230-49-0), sodium tert-butoxide (2 eq) were weighed and put into the reaction system, nitrogen was replaced, toluene, catalyst tri(dibenzylideneacetone) palladium (0.02 eq) and tri-tert-butylphosphine (0.044 eq) were added, and the mixture was refluxed at 110-120° C. for 24 h under nitrogen protection; heating was stopped after the reaction of the raw materials was completed, the mixture was cooled to 25° C., water was added for extraction and separation, the organic phase was collected, anhydrous magnesium sulfate was added to the organic phase for drying, and a crude product was obtained by rotary evaporation under reduced pressure; the crude product was purified by silica gel column chromatography using dichloromethane / hexane as eluent to obtain the compound Y086 shown;

[0130] HPLC: 99.32%; Molecular weight: 385.32; Yield: 68.5%.

[0131] 1 HNMR(500MHz,Chloroform-d)δ8.02(dd,J=8.9,1.5Hz,1H),7.87-7.76(m,4H),7.58-7.52(m,2H),7.51-7.43(m,3H),7.40-7.35(m ,2H),7.31-7.26(m,2H),7.25(dd,J=7.5,2.2Hz,1H),7.18(dd,J=7.5,2.2Hz,1H),7.13-7.09(m,2H),7.04(tt,J=7.7,1.4Hz,1H).

[0132] 1H NMR spectrum: As shown in Figure 2 the following figure.

[0133] In addition, it should be noted that other compounds of the present invention can be obtained by referring to the synthesis methods of the above-listed examples, so no further examples will be given here.

[0134] Device Example 1: Preparation of an organic light-emitting device:

[0135] ITO anode: An ITO (indium tin oxide) glass substrate with a coating thickness of was washed twice in distilled water, ultrasonically washed for 30 min, then repeatedly washed twice with distilled water, ultrasonically washed for 10 min. After washing, it was ultrasonically washed with methanol, acetone, and isopropanol in sequence (each washing for 5 min), dried, and then transferred to a plasma cleaner for washing for 5 min to obtain the ITO anode.

[0136] HIL (hole injection layer): In an evaporation machine, 4,4’,4”-tris(N-3-methylphenyl-N-phenylamino)triphenylamine (m-MTDATA) was vacuum-evaporated on the ITO anode to form a hole injection layer.

[0137] HTL (hole transport layer): NPB (i.e., N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine) was vacuum-evaporated on the hole injection layer to form a hole transport layer.

[0138] Emitting layer: The emitting layer includes a first host material, a second host material, and a guest dopant. After forming the hole injection layer and the hole transport layer, an emitting layer was formed on the HTL: The first host compound and the second host compound were used as hosts and introduced into two chambers of a vacuum vapor deposition device respectively, and the compound Z1 was introduced as a dopant into another chamber; the two host materials were evaporated at a rate of 1:1, and the dopant material was evaporated simultaneously at different rates for deposition at a doping amount of 3 wt% based on the total amount of the host and the dopant to form an emitting layer with a thickness of 40 nm on the hole transport layer.

[0139] HBL (hole blocking layer): Bis(2-methyl-8-hydroxyquinolinato-N1,O8)-(1,1'-biphenyl-4-olato)aluminum (BAlq) was vacuum-evaporated on the emitting layer to form a hole blocking layer.

[0140] ETL (electron transport layer): Aluminum 8-hydroxyquinoline (Alq 3 ) was vacuum-evaporated on the hole blocking layer to form an electron transport layer.

[0141] EIL (Electron Injection Layer): LiF is vacuum-evaporated on the electron transport layer to form the electron injection layer.

[0142] Cathode: Al is evaporated on the electron injection layer to form the cathode, and thus an organic electroluminescent device can be obtained.

[0143] Referring to the organic electroluminescent device and its preparation method provided in Device Example 1, another 50 organic electroluminescent compounds are respectively selected to replace the first host compound and the second host compound for the evaporation of the host material, and organic electroluminescent devices corresponding to the compounds are prepared.

[0144] Red light dopant material (Z1)

[0145]

[0146] Device Examples 1-25, Comparative Examples 1-5 and Parallel Examples 1-4

[0147] The device fabrication processes of Device Examples 1-25, Comparative Examples 1-5 and Parallel Examples 1-4 are exactly the same, and the same substrate material and electrode material are used, and the film thickness of the electrode material is also kept consistent. The difference lies in that: the two host materials are different, and the corresponding first host compound and second host compound in Table 1 are respectively selected, and the specific parameters are shown in Table 1.

[0148] Table 1 shows the parameters used in Device Examples 1-25, Comparative Examples 1-5 and Parallel Examples 1-4

[0149] Table 1

[0150]

[0151]

[0152] The structure of the comparative example is as follows:

[0153]

[0154] Performance detection: The driving voltage, luminous efficiency and lifespan of the organic electroluminescent devices obtained in Comparative Examples 1-5, Parallel Examples 1-4 and Device Examples 1-25 above are characterized at a brightness of 5000 (nits), and the test results are shown in Table 2 below.

[0155] Table 2

[0156]

[0157]

[0158] As can be seen from Table 2, the driving voltages of the organic electroluminescent devices provided by Examples 1-25 of the present invention and Comparative Examples 1-4 are 2.11V to 2.95V, which are significantly lower than those of Comparative Examples 1-5. At the same time, the luminous efficiency is higher than that of Comparative Examples 1-5, and the lifespan is significantly improved compared with Comparative Examples 1-5.

[0159] It can be seen from this that compared with the organic electroluminescent devices prepared using Comparative Compounds E-1, E-2, F-1, and F-2 as the double host materials of the light-emitting layer, the driving voltage of the organic electroluminescent devices prepared using the organic electroluminescent compounds provided by the present invention as the light-emitting layer materials is significantly reduced, and the luminous efficiency and lifespan are significantly improved.

[0160] This is because the triazine structure has good stability, which can increase the lifespan of the device. At the same time, the triazine structure has a strong electron-accepting ability, which can reduce the energy required for electron injection and lower the voltage required for the device to operate. 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 a strong electron-donating ability, which can improve the electron transport efficiency.

[0161] The above description of the disclosed embodiments enables those skilled in the art to implement or use the present invention. Various modifications to these embodiments will be obvious to those skilled in the art. The general principles defined herein can be implemented in other embodiments without departing from the spirit or scope of the present invention. Therefore, the present invention will not be limited to these embodiments shown herein, but will be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. A main material, characterized in that: The structure of the main material is shown in general formula 1: in, A1 and A2 are each independently selected from substituted or unsubstituted (C6-C42)aryl, substituted or unsubstituted (C3-C42)heteroaryl; D is an intermediate of the first main body, and its structure is: * represents a substitutable site.

2. The main body material according to claim 1, characterized in that A1 and A2 are each independently selected from substituted or unsubstituted (C6-C36)aryl, and substituted or unsubstituted (C3-C36)heteroaryl.

3. The main body material according to claim 1 or 2, characterized in that: The heteroaryl group includes monocyclic aromatic groups and polycyclic aromatic ring systems having at least one heteroatom, wherein the heteroatom includes but is not limited to O, S, and N; The substituted group in the "substituted or unsubstituted" is selected from deuterium, fluorine, C1-C10 alkyl, deuterium-substituted C1-C10 alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, deuterium-substituted C3-C20 cycloalkyl, deuterium-substituted C3-C20 heterocycloalkyl, and the heteroatom is selected from oxygen, nitrogen, and sulfur; or the substituted group in the "substituted or unsubstituted" is selected from the following structures:

4. The main body material according to claim 1, characterized in that The structure of the general formula 1 includes but is not limited to any one of the following compounds:

5. An organic electroluminescent material containing a double host, characterized in that: The organic electroluminescent material containing a double host comprises a first host material and a second host material, wherein the first host material is the host material according to claim 1, and the second host material has a structure shown in general formula 2: in, A3, A4, and A5 are each independently selected from substituted or unsubstituted (C6-C42)aryl, and substituted or unsubstituted (C3-C42)heteroaryl.

6. The organic electroluminescent material containing a double host according to claim 5, characterized in that: A3, A4, and A5 are each independently selected from substituted or unsubstituted (C6-C36)aryl, and substituted or unsubstituted (C3-C36)heteroaryl.

7. The organic electroluminescent material containing a double host according to claim 5 or 6, characterized in that: The heteroaryl group includes monocyclic aromatic groups and polycyclic aromatic ring systems having at least one heteroatom, wherein the heteroatom includes but is not limited to O, S, and N; The substituted group in the "substituted or unsubstituted" is selected from deuterium, fluorine, C1-C10 alkyl, deuterium-substituted C1-C10 alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, deuterium-substituted C3-C20 cycloalkyl, deuterium-substituted C3-C20 heterocycloalkyl, and the heteroatom is selected from oxygen, nitrogen, and sulfur; or the substituted group in the "substituted or unsubstituted" is selected from the following structures:

8. The organic electroluminescent material containing a double host according to claim 5, characterized in that: The structure of the general formula 2 includes but is not limited to any one of the following compounds:

9. Use of the organic electroluminescent material containing dual hosts as claimed in claim 5 in preparing an organic electroluminescent device.

10. The use according to claim 9, characterized in that: The organic electroluminescent device comprises 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 comprises a light-emitting layer; the light-emitting layer comprises a doping material and the organic electroluminescent material containing a double host.

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