A host material, an organic electroluminescent material containing a double host and an organic electroluminescent device
Patent Information
- Application Number
- CN202610809443.8
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2026-06-05
- Publication Date
- 2026-08-18
AI Technical Summary
(1)效率问题:有机电致发光器件的发光效率相对较低,需要进一步提高
噁唑基团在平面结构中可以利于电子的传输,有利于降低电压,因为碳-氘键不易断裂,做成器件不易发生生成激基复合物的现象,其含有的类噁唑结构;在降低电压的同时,其结构又打破其完全平面结构,减少了三重态-三重态泯灭,在效率上有很大优势。
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Figure CN122586942A_ABST
Abstract
Description
Technical Field
[0001] This invention belongs to the field of organic electroluminescent materials technology, specifically relating to a host material, an organic electroluminescent material containing two hosts, and an organic electroluminescent device. Background Technology
[0002] Organic light-emitting diode (OLED) technology is an electroluminescent technology that uses organic materials as the light-emitting layer. This technology offers advantages such as low driving voltage, high brightness, high efficiency, and the ability to achieve large-area flat-panel color displays. The principle of OLED is based on the fact that when a voltage is applied to the organic material, electrons and holes are injected from the cathode and anode into the organic layer, respectively, and recombine to form excitons. These excitons release energy during relaxation, generating photons, thus emitting light. In recent years, significant progress has been made in OLED technology research, including improving device efficiency, lifetime, and brightness, reducing costs, and achieving a wider color gamut. These advancements make OLED technology a promising candidate for applications in the display and lighting fields.
[0003] Organic light-emitting diode (OLED) efficiency generally refers to the device's ability 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 recombination efficiency of excitons 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] Currently, the main technical challenges of organic electroluminescent devices include the following aspects: (1) Efficiency: The luminous efficiency of organic electroluminescent devices is relatively low and needs further improvement. (2) Lifespan: The stability and durability of organic materials are poor, resulting in a short lifespan for the devices. (3) Color stability: The color of organic materials is easily affected by environmental factors such as temperature and humidity, leading to color instability. (4) Manufacturing process: The manufacturing process of organic electroluminescent devices is relatively complex and needs further optimization. (5) Cost: The high cost of organic materials and manufacturing processes limits the large-scale application of organic electroluminescent devices.
[0005] The use of a dual-host system in organic electroluminescent materials offers several advantages: Different host materials exhibit varying electron and hole transport capabilities. A dual-host system, through proper matching, can achieve a more balanced transport of electrons and holes in the emitting layer, improving exciton formation efficiency and reducing exciton quenching, thereby enhancing the device's luminous efficiency and performance. Furthermore, the dual hosts can effectively transfer excited-state energy to the emitting guest through energy transfer processes, broadening the energy transfer channels and contributing to improved energy transfer efficiency, thus enhancing the luminescent effect. Finally, the dual-host system can disperse stress, reducing the formation of crystal defects and aggregated states, thereby improving the stability and lifetime of organic electroluminescent devices and slowing down device aging and degradation.
[0006] Therefore, how to develop a long-life, low-driving-voltage organic electroluminescent material with dual host, its preparation method, and organic electroluminescent device are technical problems that urgently need to be solved by those skilled in the art. Summary of the Invention
[0007] To address the shortcomings of existing technologies, the present invention aims to provide a host material, an organic electroluminescent material containing two hosts, and an organic electroluminescent device. When the host material or the organic electroluminescent material containing two hosts of the present invention is applied to an organic electroluminescent device, it can reduce the device's driving voltage, improve luminous efficiency, and extend its lifespan.
[0008] To achieve this objective, the present invention adopts the following technical solution: On one hand, the present invention provides a main material having the structure shown in general formula 1: ; in, X represents Si and Ge; A and B rings may be absent, or when present, they may be substituted or unsubstituted C6-C12 aryl groups; L0 and L1 are each independently selected from the following: a linking bond, a substituted or unsubstituted C3-C6 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group, wherein the heteroatom is selected from one or a combination of at least two of oxygen, nitrogen, and sulfur. R1 is independently selected from substituted or unsubstituted C10-C42 aryl, substituted or unsubstituted phosphoxy, substituted or unsubstituted silyl, substituted or unsubstituted C12-C36 heteroaryl, wherein the heteroatom is selected from one or a combination of at least two of oxygen, nitrogen, sulfur, silicon, germanium, and selenium. R2 is independently selected from C10-C42 substituted or unsubstituted aryl groups, substituted or unsubstituted C12-C36 heteroaryl groups, wherein the heteroatom is selected from one or a combination of at least two of oxygen, nitrogen, sulfur, silicon, germanium, and selenium. R3 is selected from substituted or unsubstituted C6-C24 aryl or substituted or unsubstituted C3-C24 heteroaryl, wherein the heteroatom is selected from one or a combination of at least two of oxygen, nitrogen, and sulfur. R4 and R5 are each independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C6-C24 heteroaryl; their heteroatoms are selected from one or a combination of at least two of oxygen, nitrogen, and sulfur. R4 and R5 can have the same substituent, different substituents, or they can form a ring.
[0009] In general formula 1, the hydrogen atoms are either completely unsubstituted by deuterium, completely substituted by deuterium, or partially substituted by deuterium.
[0010] Preferably, L0 and L1 are each independently selected from the linking bond, substituted or unsubstituted C10-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl, and their heteroatoms are selected from one or a combination of at least two of oxygen, nitrogen, and sulfur. R1 is independently selected from substituted or unsubstituted C10-C24 aryl, substituted or unsubstituted phosphoxy, substituted or unsubstituted silyl, substituted or unsubstituted C12-C24 heteroaryl, wherein the heteroatom is selected from one or a combination of at least two of oxygen, nitrogen, sulfur, silicon, and selenium. R2 is independently selected from substituted or unsubstituted phosphoxy, substituted or unsubstituted silyl, substituted or unsubstituted aryl, substituted or unsubstituted C12-C24 heteroaryl, wherein the heteroatom is selected from one or a combination of at least two of oxygen, nitrogen, sulfur, silicon, germanium, and selenium. R4 and R5 are each independently selected from methyl, substituted or unsubstituted C6-C12 aryl groups; R4 and R5 can have the same substituent, different substituents, or they can form a ring.
[0011] Preferably, X is selected from Si.
[0012] Preferably, the main material has the structure shown in Formula 1-1: L0 and L1 are each independently selected from the following: linked bonds, substituted or unsubstituted biphenyls, substituted or unsubstituted naphthalenes, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrenes, substituted or unsubstituted dibenzofurans, substituted or unsubstituted dibenzothiophenes, substituted or unsubstituted fluorenes, or substituted or unsubstituted carbazoles. R1 is selected from one or more of the following structures, substituted or unsubstituted: The dashed lines represent the bonding sites of the functional groups.
[0013] R2 is selected from one or more of the following structures, substituted or unsubstituted: The dashed lines represent the bonding sites of the functional groups.
[0014] R3 is selected from one or a combination of two or more of the following structures, substituted or unsubstituted: ; The dashed lines represent the bonding sites of the functional groups.
[0015] R4 and R5 are independently selected from one or more combinations of the following structures, whether substituted or unsubstituted: .
[0016] The dashed lines represent the bonding sites of the functional groups.
[0017] In the above technical solution, the term "substituted or unsubstituted" means that the group may not be substituted, or may be substituted by one or more substituents. The "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, 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 as or different from each other.
[0018] In this invention, the substituents in the substituted group in the term "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 heteroatom is selected from one or a combination of at least two of oxygen, nitrogen, and sulfur.
[0019] In this invention, among the groups defined by R1-R5 as described above, the combination of "one or more combinations selected from substituted or unsubstituted structures" refers to a group formed by two or more groups linked by chemical bonds, such as single bonds.
[0020] In this invention, the hydrogen atoms in the groups can be completely unsubstituted by deuterium, completely substituted by deuterium, or partially substituted by deuterium.
[0021] In the technical solution of this invention, the main material is selected from any one of the following compounds, but is not limited to the following structures: ; Where D represents deuterium.
[0022] The second technical objective of this invention is to provide an organic electroluminescent material containing two main bodies, wherein the organic electroluminescent material containing two main bodies includes a first main body material and a second main body material, the first main body material being the aforementioned main body material, and the second main body material having the structure shown in general formula 2: General Formula 2 Wherein, L3, L4, and L5 are connecting bonds, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C6-C30 aromatic amino groups, and substituted or unsubstituted C3-C30 heteroaryl amino groups, and their heteroatoms are selected from one or a combination of at least two 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 a combination of at least two of oxygen, nitrogen, sulfur, silicon, and selenium.
[0023] Preferably, L3, L4, and L5 are connecting bonds, substituted or unsubstituted C6-C18 aryl groups, substituted or unsubstituted C3-C12 heteroaryl groups, substituted or unsubstituted C6-C18 aromatic amino groups, or substituted or unsubstituted C3-C18 heteroaryl amino groups, wherein the heteroatoms are selected from one or a combination of at least two 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 a combination of at least two of oxygen, nitrogen, sulfur, silicon, and selenium.
[0024] 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: ; Where D represents deuterium.
[0025] 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 intermediates of Formula 1-1: (1) Under nitrogen protection, reactant 1 (1 eq), reactant 2 (1-1.3 eq), potassium carbonate (2-3 eq) were weighed and placed into the reaction system. Toluene, ethanol, water and catalyst tetra(triphenylphosphine)palladium (0.01-0.05 eq) were added. The reaction was carried out at 80-90℃ for 24-28 h under nitrogen protection. After the reaction was completed, the mixture was cooled to 25℃ and treated to obtain HT-1 as shown. (2) Under nitrogen protection, HT-1 (1 eq), pinacol diboronate (1.2-1.5 eq), and potassium acetate (2-3 eq) were added to the reaction system, along with 1,4-dioxane, catalyst tris(dibenzylideneacetone)palladium (0.01-0.03 eq) and X-phos (0.04-0.08 eq). The reaction was carried out at 100-110℃ for 24-28 hours under nitrogen protection. After the reaction was completed, the mixture was cooled to 25℃ and treated to obtain the compound HT-2 shown. (3) Under nitrogen protection, weigh reactant 3 (1 eq), reactant 4 (1-1.2 eq), potassium carbonate (2-3 eq) and put them into the reaction system. Add toluene, ethanol, water and catalyst tetra(triphenylphosphine)palladium (0.01-0.05 eq). React at 80-90℃ for 24-28 hours under nitrogen protection. After the reaction is completed, cool to 25℃ and treat to obtain HT-3 as shown. (4) Under nitrogen protection, weigh HT-3 (1 eq), reactant 5 (1-1.1 eq), potassium carbonate (2-3 eq) and put them into the reaction system. Add toluene, ethanol, water and catalyst tetra(triphenylphosphine)palladium (0.01-0.05 eq). React at 80~90℃ for 24h under nitrogen protection. After the reaction is completed, cool to 25℃ and treat to obtain HT-4 as shown. II. Preparation of General Formula 1-1: (1) Under nitrogen protection, weigh HT-2 (1 eq), HT-4 (1-1.1 eq), potassium carbonate (2-3 eq) and put them into the reaction system. Add toluene, ethanol, water and catalyst tetra(triphenylphosphine)palladium (0.01-0.05 eq). React at 80-90℃ for 24-26 hours under nitrogen protection. After the reaction is completed, cool to 25℃ and treat to obtain the compound shown in Formula 1-1. The purpose of this invention is to provide an application of a dual-host organic electroluminescent material in the fabrication of organic electroluminescent devices.
[0026] The present invention provides an organic electroluminescent device, the organic electroluminescent device comprising a first electrode, a second electrode, and an organic electroluminescent material layer disposed between the first electrode and the second electrode; the organic electroluminescent material layer comprises a light-emitting layer; the light-emitting layer comprises a doped material and a dual-host organic electroluminescent material as described above.
[0027] Preferably, the mass ratio of the first host material, the second host material, and the dopant material in the dual-host organic electroluminescent material is (1~99):(1~99):(99~1), for example, 1:1:98, 1:2:97, 1:20:2, 1:1:9, 1:3:5, 1:4:9, 1:10:1, 1:20:1, 2:5:1, 3:5:8, 5:10:1, 15:10:1, 20:1:9, 20:10:9, 99:1:1, 80:1:1, 1:80:1, 1:99:1, etc., preferably (1~20):(1~20):(9~1), more preferably 10:10:1.
[0028] More specifically, the organic electroluminescent device includes an anode (first electrode), a hole transport region, a light-emitting layer, an electron transport region, and a cathode (second electrode). The light-emitting layer includes a first host material as shown in Formula 1 and a second host material as shown in Formula 2.
[0029] 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.
[0030] 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.
[0031] 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.
[0032] 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. 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, etc.
[0033] 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.
[0034] 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.
[0035] The main material of the light-emitting layer is selected from the structure of this invention.
[0036] 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.
[0037] The electron transport layer can promote electron transport. Electron transport materials are materials with high electron mobility that can effectively receive electrons from the cathode and transport them to the light-emitting layer.
[0038] The materials of the electron transport layer include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic free radical compounds; hydroxyflavonoid-metal complexes, etc.
[0039] Preferably, the thickness of the electron transport layer can be from 1 nm to 50 nm. An electron transport layer with a thickness of 1 nm or more has the advantage of preventing a decrease in electron transport characteristics, and an electron transport layer with a thickness of 50 nm or less has the advantage of preventing an increase in driving voltage caused by an excessively thick electron transport layer.
[0040] The electron injection layer can promote electron injection, and the electron injection material preferably has the ability to transport electrons, has the electron injection effect from the cathode, has an excellent electron injection effect on the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from migrating to the hole injection layer, and has excellent thin film forming ability.
[0041] The material of the electron injection layer may be, for example, fluorenone, anthraquinone dimethane, biphenylquinone, thiam dioxide, azole, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenemethane, anthrone and its derivatives, metal complexes, nitrogen-containing five-membered ring derivatives, etc., but is not limited thereto.
[0042] Depending on the materials used, the above-mentioned organic electroluminescent devices can be top-emitting, bottom-emitting, or bilaterally emitting.
[0043] The organic electroluminescent device described in this invention can be used in organic solar cells, electronic paper, organic photoreceptors, or organic thin-film transistors.
[0044] Compared with the prior art, the present invention has the following beneficial effects: The main material of this invention contains oxazole structures, deuterated structures, and oxazole-like structures, thereby having the following advantages: The oxazole group in the planar structure can facilitate electron transport and help reduce voltage because the carbon-deuterium bond is not easy to break. When the device is made, it is less likely to generate excitocomplexes. It contains an oxazole-like structure. While reducing voltage, its structure breaks its completely planar structure, reducing triplet-triplet annihilation, which has a great advantage in efficiency.
[0045] Compared to electronic devices obtained using conventional compounds, electronic devices obtained using the compounds according to the present invention exhibit very high stability and very long lifetime. The compounds of the present invention have low operating voltage and high efficiency. The selection of larger molecular weight groups in R1 and R2 distinguishes them from the steric characteristics of a single benzene ring, particularly in terms of layer uniformity. The compounds of the present invention can be produced very quickly and easily using conventional methods, thus also achieving a cost advantage. Attached Figure Description
[0046] Figure 1 The nuclear magnetic resonance hydrogen spectrum of compound H001 prepared in Example 1. Detailed Implementation
[0047] 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.
[0048] 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 operation issues, each number should be understood as an approximation rather than an absolutely accurate value.
[0049] Example 1 Preparation of compound H001 (1) Under nitrogen protection, HT-2 (1 eq, CAS: 2392155-14-3), HT-4 (1 eq, CAS: 1812210-55-1), and potassium carbonate (2.5 eq) were weighed and added to the reaction system. Toluene, ethanol, water, and catalyst tetra(triphenylphosphine)palladium (0.01 eq) were added. The reaction was carried out at 90°C for 24 h under nitrogen protection. Heating was stopped after the reactants had reacted completely. The mixture was cooled to 25°C and the crude product was purified by recrystallization from toluene / ethyl acetate to obtain compound H001, with a yield of 69.56%. HPLC: 99.98%; Molecular weight: 693.31; Elemental analysis results: C: 84.82%; H: 5.08%; N: 6.06%; O: 4.05%.
[0050] The proton NMR spectrum is as follows: Figure 1 As shown.
[0051] Example 2 Preparation of compound H2-103 Under nitrogen protection, reactant 1 (1 eq, CAS: 2085325-19-3), reactant 2 (1 eq, CAS: 1427556-45-3), and sodium tert-butoxide (2.5 eq) were weighed and added to the reaction system. Dry toluene, catalyst tris(dibenzylacetone)palladium (0.02 eq), and 50% tri-tert-butylphosphine (0.044) were added. The mixture was refluxed at 120 °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 H2-103 shown.
[0052] HPLC: 99.94%; Molecular weight: 628.40; Elemental analysis results: C: 85.87%; H: 4.52%; N: 4.59%; O: 5.22%; Yield: 72.36%.
[0053] 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.
[0054] Device Example 1 Fabrication of organic electroluminescent devices ITO anode: An ITO (indium tin oxide)-Ag-ITO (indium tin oxide) glass substrate with a coating thickness of 1500 Å was cleaned twice with distilled water and ultrasonically washed for 30 min. Then it was cleaned twice more with distilled water and ultrasonically washed for 10 min. After washing, it was ultrasonically washed sequentially with methanol, acetone and isopropanol (5 min each time), dried, and then transferred to a plasma cleaner for 5 min to obtain the ITO anode.
[0055] 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.
[0056] 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.
[0057] 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.
[0058] 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.
[0059] 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.
[0060] EIL (Electron Injection Layer): LiF 210Å is vacuum-deposited on the electron transport layer to form the electron injection layer.
[0061] 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. 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.
[0062] Red-light doped material (Z1) .
[0063] Device Examples 1-50, Comparative Examples 1-20 The device fabrication processes of Device Examples 1-50 and Comparative Examples 1-20 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 host materials are different, and the corresponding first host compound and second host compound in Table 1 are selected respectively.
[0064] The structures of the compounds used in the comparative examples are shown below: Performance testing: The driving voltage, luminous efficiency and lifetime of the organic electroluminescent devices obtained in Comparative Examples 1-20 and Device Examples 1-50 were characterized at a brightness of 7000 nits. The test results are shown in Table 2.
[0065] Table 2. Performance Test Results As can be seen from Table 2, the driving voltage of the dual-subject organic electroluminescent device provided by Device Examples 1-50 is 3.20V~3.61V, which is significantly lower than that of Comparative Examples 1-20. The luminous efficiency of Device Examples 1-50 is 123 cd / A-148 cd / A, which is higher than that of Comparative Examples 1-20. The lifetime of Device Examples 1-50 is 1629h-1740h, which is significantly improved compared with Comparative Examples 1-20.
[0066] Devices 5, 6, and 30 exhibit high voltage, low efficiency, and short lifetime because the carbazole and thiophene groups are strong electron-withdrawing groups, resulting in uneven electron cloud distribution. Devices 12, 13, 21, 22, 37, 38, and 43, while having slightly higher voltage values, have significantly longer lifetimes compared to the others, due to fewer triplet-triplet annihilation events in the oxazole groups. Devices 45, 46, and 47 have even longer lifetimes because carbon-deuterium bonds are more stable than carbon-carbon bonds. Devices 7, 8, 9, 10, 19, 20, and 40 have high voltage but low lifetimes due to their large molecular weight and excessively long π-π bond conjugation. Devices 14, 15, 28, 39, and 44 have higher efficiency than other device examples because they contain oxazole-like structures; significant efficiency roll-off is rarely observed.
[0067] Therefore, it can be seen that the organic electroluminescent device prepared by using the organic electroluminescent compound as the light-emitting layer material provided by the present invention has a significantly lower driving voltage and a significantly improved luminous efficiency and lifetime compared with the organic electroluminescent devices prepared by using Comparative Examples 1-20 as the dual host materials for the light-emitting layer.
[0068] The applicant declares that the present invention is illustrated through the above embodiments to describe the main material, the organic electroluminescent material containing two main components, and the organic electroluminescent device of the present invention. However, the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments 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 has the structure shown in Formula 1: ; in, X represents Si and Ge; A and B may not exist, or when they do exist, they may be substituted or unsubstituted C6-C12 aryl groups. L0 and L1 are each independently selected from the following: a linking bond, a substituted or unsubstituted C3-C6 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group, wherein the heteroatom is selected from one or a combination of at least two of oxygen, nitrogen, and sulfur. R1 is independently selected from substituted or unsubstituted C10-C42 aryl, substituted or unsubstituted phosphoxy, substituted or unsubstituted silyl, substituted or unsubstituted C12-C36 heteroaryl, wherein the heteroatom is selected from one or a combination of at least two of oxygen, nitrogen, sulfur, silicon, germanium, and selenium. R2 is independently selected from 10-C42 substituted or unsubstituted aryl groups, substituted or unsubstituted C12-C36 heteroaryl groups, wherein the heteroatom is selected from one or a combination of at least two of oxygen, nitrogen, sulfur, silicon, germanium, and selenium. R3 is selected from substituted or unsubstituted C6-C24 aryl or substituted or unsubstituted C3-C24 heteroaryl, wherein the heteroatom is selected from one or a combination of at least two of oxygen, nitrogen, and sulfur. R4 and R5 are each independently selected from substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C6-C24 heteroaryl; their heteroatoms are selected from one or a combination of at least two of oxygen, nitrogen, and sulfur. R4 and R5 may be the same substituent or different substituents, or R4 and R5 may be linked together to form a ring; In general formula 1, the hydrogen atoms are either completely unsubstituted by deuterium, completely substituted by deuterium, or partially substituted by deuterium.
2. The main material according to claim 1, characterized in that, L0 and L1 are each independently selected from the linking bond, substituted or unsubstituted C10-C18 aryl, substituted or unsubstituted C3-C18 heteroaryl, and their heteroatoms are selected from one or a combination of at least two of oxygen, nitrogen, and sulfur. R1 is independently selected from substituted or unsubstituted C10-C24 aryl, substituted or unsubstituted phosphoxy, substituted or unsubstituted silyl, substituted or unsubstituted C12-C24 heteroaryl, wherein the heteroatom is selected from one or a combination of at least two of oxygen, nitrogen, sulfur, silicon, and selenium. R2 is independently selected from substituted or unsubstituted phosphoxy, substituted or unsubstituted silyl, substituted or unsubstituted aryl, substituted or unsubstituted C12-C24 heteroaryl, wherein the heteroatom is selected from one or a combination of at least two of oxygen, nitrogen, sulfur, silicon, germanium, and selenium. R4 and R5 are each independently selected from methyl, substituted or unsubstituted C6-C12 aryl groups; R4 and R5 may be the same or different substituents, or R4 and R5 may be linked together to form a ring.
3. The main material according to claim 1, characterized in that, X is selected from Si.
4. The main material according to claim 1, characterized in that, The main material has the structure shown in Formula 1-1: ; The definitions of L0, L1, R1, R2, R3, R4, and R5 are the same as in claim 1.
5. The main material according to claim 4, characterized in that, L0 and L1 are each independently selected from the following: linked bonds, substituted or unsubstituted biphenyls, substituted or unsubstituted naphthalenes, substituted or unsubstituted anthracene, substituted or unsubstituted phenanthrenes, substituted or unsubstituted dibenzofurans, substituted or unsubstituted dibenzothiophenes, substituted or unsubstituted fluorenes, or substituted or unsubstituted carbazoles. R1 is selected from one or more of the following structures, substituted or unsubstituted: ; Dashed lines represent the bonding sites of functional groups; R2 is selected from one or more of the following structures, substituted or unsubstituted: ; Dashed lines represent the bonding sites of functional groups; R3 is selected from one or a combination of two or more of the following structures, substituted or unsubstituted: ; ; Dashed lines represent the bonding sites of functional groups; R4 and R5 are independently selected from one or more combinations of the following structures, whether substituted or unsubstituted: ; The dashed lines represent the bonding sites of the functional groups.
6. The main material according to claim 1, characterized in that, 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 a combination of at least two of oxygen, nitrogen, and sulfur.
7. The main material according to claim 1, characterized in that, The host material is selected from any one of the following compounds: 。 8. 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 according to any one of claims 1-7, and the second host material has the structure shown in general formula 2: ; General Formula 2 Wherein, L3, L4, and L5 are connecting bonds, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 heteroaryl groups, substituted or unsubstituted C6-C30 aromatic amino groups, and substituted or unsubstituted C3-C30 heteroaryl amino groups, and their heteroatoms are selected from one or a combination of at least two 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 a combination of at least two of oxygen, nitrogen, sulfur, silicon, and selenium; Preferably, L3, L4, and L5 are connecting bonds, substituted or unsubstituted C6-C18 aryl groups, substituted or unsubstituted C3-C12 heteroaryl groups, substituted or unsubstituted C6-C18 aromatic amino groups, or substituted or unsubstituted C3-C18 heteroaryl amino groups, wherein the heteroatoms are selected from one or a combination of at least two 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 a combination of at least two of oxygen, nitrogen, sulfur, silicon, and selenium.
9. The organic electroluminescent material containing two main bodies according to claim 8, characterized in that, The second host material is selected from any one of the following compounds: 。 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; the organic electroluminescent material layer includes a light-emitting layer; the light-emitting layer includes a doped material and the dual-host organic electroluminescent material as described in claim 8 or 9.