A host material, an organic electroluminescent material containing a double host and an organic electroluminescent device
By using dual host materials to disperse triplet excitons, the problems of easy oxidation and humidity influence on OLED materials were solved, realizing an organic electroluminescent device with low driving voltage and high efficiency, and extending the device lifespan.
Patent Information
- Application Number
- CN202510838621.5
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2025-06-23
- Publication Date
- 2025-11-21
- Estimated Expiration
- 2045-06-23
AI Technical Summary
Existing OLED materials are susceptible to oxidation and humidity, resulting in short lifespans, low luminous efficiency, and difficulty in achieving high performance and long lifespan.
By employing a dual-host material, triplet excitons are dispersed on two hosts, reducing triplet-triplet annihilation, improving electron mobility and structural stability, and using host materials with specific structures to reduce driving voltage and improve luminescence efficiency and lifetime.
By reducing the driving voltage, the luminous efficiency and lifespan of organic electroluminescent devices are improved, demonstrating good application effects and industrialization prospects.
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Figure CN120365224B_ABST
Abstract
Description
Technical Field
[0001] This invention belongs to the field of organic electroluminescent materials, specifically relating to a host material, an organic electroluminescent material containing two hosts, and an organic electroluminescent device. Background Technology
[0002] As early as 1936, Destrian created the first Organic Light Emitting Diode (OLED) by dispersing organic fluorescent compounds in polymers to form thin films. Researchers then observed the generation of excitation light by applying voltage to these materials. From this point onward, research on OLEDs gradually intensified. Their practical applications in manufacturing new display products and lighting products have made their market prospects very broad. Currently, OLEDs are used in display technologies such as smartphones and tablets. However, the organic light-emitting materials at the core of OLEDs are susceptible to oxidation and humidity, resulting in a significantly shorter lifespan compared to inorganic materials. Furthermore, the materials at each pixel level also face challenges related to light decay. Therefore, further research is needed to improve the luminous efficiency and lifespan of OLEDs.
[0003] OLED devices mainly consist of several parts: an anode, a cathode, an organic semiconductor layer, and a charge transport layer. When a voltage is applied to an OLED device, electrons are injected from the cathode into the organic semiconductor layer, while holes are injected from the anode. These electrons and holes meet in the organic semiconductor layer and combine to form electron-hole pairs, or excitons. These excitons migrate within the organic semiconductor layer, and when they encounter a light-emitting center, they release photons, thus producing visible light. Furthermore, by doping with metal complexes such as platinum, iridium, and osmium, triplet excitons from organic molecules can be transferred to the triplet state of the metal complex, improving the efficiency of organic light-emitting devices. However, the most critical aspects for achieving large-scale industrialization of organic electroluminescent devices are high device performance and long lifespan.
[0004] Therefore, how to provide a long-life, low-driving-voltage organic electroluminescent material and organic electroluminescent device with dual host is a technical problem that urgently needs to be solved by those skilled in the art. Summary of the Invention
[0005] In view of this, the present invention provides a host material, an organic electroluminescent material containing two hosts, and an organic electroluminescent device. By using a dual-host material to disperse triplet excitons on two hosts, triplet-triplet annihilation (TTA) is reduced, thereby lowering the driving voltage of the organic electroluminescent device while improving the device's luminous efficiency and lifespan.
[0006] It should be noted that this invention provides an organic electroluminescent device with dual hosts, wherein the first host compound has a faster electron mobility and a stable structure. By using dual host materials, triplet excitons can be dispersed on two hosts, which can reduce triplet-triplet annihilation (TTA). When both are used as hosts of the light-emitting layer, the driving voltage of the organic electroluminescent device is reduced, while the efficiency and lifetime of the device are improved.
[0007] To achieve the above objectives, the present invention adopts the following technical solution:
[0008] The first technical objective of this invention is to provide a main material, the structure of which is shown in general formula 1:
[0009] ;
[0010] in,
[0011] X is selected from -N=, -O-, or -S-;
[0012] Y is selected from -N=, -O-, or -S-;
[0013] When X is selected from -N=, Y is selected from -O- or -S-;
[0014] Ar is selected from substituted or unsubstituted C6 aryl, substituted or unsubstituted C6 deuterated aryl;
[0015] R1, R2, and R3 are each independently selected from any one of the following: substituted or unsubstituted C6-C42 aryl, substituted or unsubstituted C6-C30 heteroaryl, substituted or unsubstituted C6-C18 deuterated aryl, and substituted or unsubstituted C12-C24 phenylamino.
[0016] L1, L2, and L3 are each independently selected from any one of single-bonded, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C6-C30 heteroarylene.
[0017] Furthermore, all hydrogen atoms not described in the above general formula 1 can be independently substituted with or not substituted with deuterium.
[0018] In the formula, R1, R2, and R3 are each independently selected from the following structures and any combination thereof:
[0019] ;
[0020] L1, L2, and L3 are independently selected from the linking bond, phenyl, or naphthyl group.
[0021] In the above technical solution, "substituted or unsubstituted" means that the group can be unsubstituted or substituted by one or more substituents. "Substitution" means that the hydrogen atom bonded to the carbon atom of the compound becomes another substituent. 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 can be the same as or different from each other.
[0022] Furthermore, the heteroaryl group includes a monocyclic aromatic group and a polycyclic aromatic ring system with at least one heteroatom, and the heteroatom includes, but is not limited to, O, S, N, and P.
[0023] The substituted group in "substituted or unsubstituted" is selected from deuterium, fluorine, C1-C10 alkyl, deuterated C1-C10 alkyl, C3-C10 cycloalkyl, C3-C10 heterocyclic alkyl, and deuterated C3-C10 heterocyclic alkyl, wherein the heteroatom is selected from oxygen, nitrogen, and sulfur; and the substituted group in "substituted or unsubstituted" may also be selected from the following structures: .
[0024] In the technical solution of this invention, the general formula 1 specifically has the following structure, but is not limited thereto:
[0025]
[0026]
[0027]
[0028]
[0029]
[0030]
[0031]
[0032]
[0033]
[0034]
[0035] .
[0036] The above are some specific structural forms of the main materials, but are not limited to the chemical structures listed. All compounds based on the general structural formula shown in Formula 1, with simple transformations of groups within the defined range, should be included.
[0037] 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 comprises a main body material (first main body material) and a second main body material as described above, and the mass ratio of the first main body material to the second main body material is 1:99-99:1; the first main body material has the structure shown in general formula 1, and the second main body material has the structure shown in general formula 2.
[0038] ;
[0039] D1, D2, and D3 are each independently selected from any one of substituted or unsubstituted C6-C42 aryl and substituted or unsubstituted C6-C42 heteroaryl.
[0040] L4, L5, and L6 are each independently selected from the linking bond, substituted or unsubstituted (C6-C18) aryl group.
[0041] Furthermore, D1 and D2 are selected from (C6-C18) substituted or unsubstituted aryl groups;
[0042] D3 is selected from substituted or unsubstituted (C6-C36) aryl or substituted or unsubstituted (C6-C30) heteroaryl.
[0043] Furthermore, D1 is selected from substituted or unsubstituted phenyl, biphenyl, or terphenyl;
[0044] D2 is selected from substituted or unsubstituted phenyl, naphthyl, biphenyl, terphenyl, and benzophenanthryl;
[0045] D3 is selected from substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C6-C24) heteroaryl;
[0046] L4, L5, and L6 are each independently selected from the linking bond, phenyl, or naphthyl group.
[0047] In the above technical solution, "substituted or unsubstituted" means that the group can be unsubstituted or substituted by one or more substituents. "Substitution" means that the hydrogen atom bonded to the carbon atom of the compound becomes another substituent. 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 can be the same as or different from each other.
[0048] Heteroaryl groups include monocyclic aromatic groups and polycyclic aromatic ring systems with at least one heteroatom, and heteroatoms include, but are not limited to, O, S, N, and P.
[0049] The substituted group in "substituted or unsubstituted" is selected from deuterium, fluorine, C1-C10 alkyl, deuterated C1-C10 alkyl, C3-C10 cycloalkyl, C3-C10 heterocyclic alkyl, and deuterated C3-C10 heterocyclic alkyl, wherein the heteroatom is selected from oxygen, nitrogen, and sulfur; and the substituted group in "substituted or unsubstituted" may also be selected from the following structures:
[0050] .
[0051] In the technical solution of this invention, the second main material (general formula 2) is selected from any one of the following compounds:
[0052]
[0053]
[0054]
[0055]
[0056]
[0057]
[0058]
[0059]
[0060]
[0061]
[0062]
[0063]
[0064]
[0065]
[0066]
[0067] .
[0068] The present invention also provides a method for preparing the above-mentioned organic electroluminescent material containing two main bodies.
[0069] The preparation method of general formula 1 specifically includes the following steps:
[0070] (1) Under nitrogen protection, reactant 1 (1 eq) and reactant 2 (1-1.2 eq) were weighed. Reactant 1 was completely dissolved in the reaction system, and then one-tenth of reactant 2 was added. Carbon tetrachloride and benzoyl peroxide (0.02-0.03 eq) were added as catalyst. The remaining reactant 2 was added at 40°C under nitrogen protection. The mixture was refluxed for 4 h, then cooled to 25°C, and pure water was added. After stirring for 30 min, the mixture was allowed to stand for separation, and the layers were separated by column chromatography to obtain compound R-1 as shown.
[0071] (2) Under nitrogen protection, weigh R-1 (1 eq), reactant 3 (1-1.2 eq), sodium tert-butoxide (2-3 eq) and add them to the reaction system. Add toluene, catalyst tris(dibenzylacetone) bispalladium (0.02-0.03 eq) and tritert-butylphosphine (0.04-0.06 eq), reflux at 90-120℃ for 24 h under nitrogen protection, then cool to 25℃, add pure water, stir for 30 min and let stand to separate the layers, separate the liquid and column chromatography to obtain compound R-2 as shown.
[0072] (3) Under nitrogen protection, compound R-2 (1 eq), reactant 4 (1-1.2 eq), potassium carbonate (2-3 eq) were weighed and added to the reaction system. THF, water, and catalyst tetrakis(triphenylphosphine)palladium (0.02-0.03 eq) were added. The mixture was refluxed at 70°C for 24 h under nitrogen protection, then cooled to 25°C, purified water was added, and the mixture was stirred for 30 min. After standing and separating the layers, the mixture was separated and subjected to column chromatography to obtain compound (general formula 1).
[0073] The specific synthesis route is as follows:
[0074] .
[0075] Furthermore, the preparation method of general formula 2 specifically includes the following steps:
[0076] (1) Under nitrogen protection, reactant 1 (1 eq), reactant 2 (1-1.2 eq), potassium carbonate (3-4 eq) were weighed and added to the reaction system. Toluene, ethanol, water and catalyst tetra(triphenylphosphine)palladium (0.05-0.08 eq) were added. The mixture was refluxed at 90 °C for 24 h under nitrogen protection, then cooled to 25 °C, filtered, and subjected to solid column chromatography to obtain compound H-1 as shown.
[0077] (2) Under nitrogen protection, weigh H-1 (1 eq), reactant 2-1 (1-1.2 eq), potassium carbonate (3-4 eq) and put them into the reaction system. Add toluene, ethanol, water and catalyst tetra(triphenylphosphine)palladium (0.05-0.08 eq). Reflux at 90-100℃ for 24 h under nitrogen protection, then cool to 25℃, filter, and perform solid column chromatography to obtain compound H-2 as shown.
[0078] (3) Under nitrogen protection, weigh H-2 (1 eq), reactant 2-2 (1-1.2 eq), potassium carbonate (3-4 eq) and add them to the reaction system. Add toluene, ethanol, water and catalyst tetra(triphenylphosphine)palladium (0.05-0.08 eq). Reflux at 90-100℃ for 24 h under nitrogen protection, then cool to 25℃, filter, and perform solid column chromatography to obtain compound (general formula 2).
[0079] The specific synthesis route is as follows:
[0080] .
[0081] Furthermore, this invention also seeks protection for the use of the above-mentioned organic electroluminescent material containing two main bodies in the preparation of organic electroluminescent devices.
[0082] 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 two hosts as described above; the mass ratio of the organic electroluminescent material containing two hosts to the doped material is (1~99):(99~1).
[0083] 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 host material (first host material) as shown in Formula 1 and a second host material as shown in Formula 2.
[0084] 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.
[0085] 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; but are not limited thereto.
[0086] 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.
[0087] 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.
[0088] 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.
[0089] The main material of the light-emitting layer is selected from the structure of this invention.
[0090] 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.
[0091] 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.
[0092] 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.
[0093] Depending on the materials used, the above-mentioned organic electroluminescent devices can be top-emitting, bottom-emitting, or bilaterally emitting.
[0094] 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.
[0095] As can be seen from the above technical solution, the present invention has the following beneficial effects:
[0096] 1) When the first host material alters the fusion position of naphthalene and oxazole, its molecular structure changes, leading to changes in the energy levels of the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO). During matching with the second host material, the charge injection barrier decreases, thereby reducing the driving voltage.
[0097] 2) In the organic electroluminescent device with dual hosts, the first host compound has a faster electron mobility and a stable structure. By using a dual host material to disperse triplet excitons on two hosts, triplet-triplet annihilation is reduced. This lowers the driving voltage of the organic electroluminescent device while improving its luminous efficiency and lifespan, demonstrating good application effects and industrialization prospects. Attached Figure Description
[0098] To more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are only embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on the provided drawings without creative effort.
[0099] Figure 1 The above is the proton NMR spectrum of compound R003 in Example 1 of this invention. Detailed Implementation
[0100] The technical solution of the present invention will be clearly and completely described below with reference to the embodiments and related drawings. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without creative effort are within the scope of protection of the present invention.
[0101] This invention discloses a method for preparing a dual-host organic electroluminescent material.
[0102] Additionally, it should be noted that the values given in the following embodiments are as accurate as possible; however, those skilled in the art will understand that due to unavoidable measurement errors and experimental issues, each number should be understood as an approximation rather than an absolutely accurate value.
[0103] Example 1: Preparation of compound R003
[0104]
[0105] Under nitrogen protection, reactant 1 (CAS No.: 439607-91-7) (1 eq) and reactant 2 (CAS No.: 3493-39-8) (1.2 eq) were weighed. Reactant 1 was completely dissolved in the reaction system, and then one-tenth of reactant 2 was added. Carbon tetrachloride and benzoyl peroxide (0.03 eq) were added as catalysts. The remaining reactant 2 was added at 40°C under nitrogen protection, and the mixture was refluxed for 4 h. Then it was cooled to 25°C, purified water was added, and the mixture was stirred for 30 min. After standing and separating the layers, the mixture was separated and subjected to column chromatography to obtain compound R003-1 (test value: 282.52, yield: 75.8%).
[0106]
[0107] Under nitrogen protection, R003-1 (1 eq), reactant 3 (CAS No.: 620-84-8) (1 eq), and sodium tert-butoxide (3 eq) were weighed and added to the reaction system. Toluene, tris(dibenzylacetone) bispalladium catalyst (0.03 eq) and tri-tert-butylphosphine (0.06 eq) were added. The mixture was refluxed at 120 °C for 24 h under nitrogen protection, then cooled to 25 °C, purified water was added, and the mixture was stirred for 30 min. After standing and separating the layers, the mixture was separated and subjected to column chromatography to obtain compound R003-2 (test value: 370.84, yield: 82.3%).
[0108]
[0109] Under nitrogen protection, compound R003-2 (1 eq), reactant 4 (CAS No.: 98-80-6) (1.2 eq), and potassium carbonate (3 eq) were weighed and added to the reaction system. THF, water, and catalyst tetrakis(triphenylphosphine)palladium (0.03 eq) were added. The mixture was refluxed at 70 °C for 24 h under nitrogen protection, then cooled to 25 °C, purified water was added, and the mixture was stirred for 30 min. After standing and separating the layers, the mixture was separated and subjected to column chromatography to obtain compound R003 (test value: 472.49, yield: 72.3%).
[0110] Example 2: Preparation of compound H020
[0111]
[0112] Under nitrogen protection, reactant 1 (CAS: 108-77-0) (1 eq), reactant 2 (CAS: 98-80-6) (1.2 eq), and potassium carbonate (4 eq) were weighed and added to the reaction system. Toluene, ethanol, water, and tetrakis(triphenylphosphine)palladium catalyst (0.08 eq) were added. The mixture was refluxed at 90 °C for 24 h under nitrogen protection, then cooled to 25 °C, filtered, and subjected to solid column chromatography to obtain compound H020-1 (test value: 225.49, yield 66.7%).
[0113]
[0114] Under nitrogen protection, H020-1 (1 eq), reactant 2-1 (CAS: 98-80-6) (1 eq), and potassium carbonate (4 eq) were weighed and added to the reaction system. Toluene, ethanol, water, and tetrakis(triphenylphosphine)palladium catalyst (0.08 eq) were added. The mixture was refluxed at 90 °C for 24 h under nitrogen protection, then cooled to 25 °C, filtered, and subjected to solid column chromatography to obtain compound H020-2 (test value: 267.56, yield 68.2%).
[0115]
[0116] Under nitrogen protection, H020-2 (1 eq), reactant 2-2 (CAS: 128388-54-5) (1 eq), and potassium carbonate (4 eq) were weighed and added to the reaction system. Toluene, ethanol, water, and tetrakis(triphenylphosphine)palladium catalyst (0.08 eq) were added. The mixture was refluxed at 90 °C for 24 h under nitrogen protection, then cooled to 25 °C, filtered, and subjected to solid column chromatography to obtain the compound H020 shown (test value: 416.54, yield 48.7%).
[0117] It should be noted that other compounds of the present invention can be obtained by referring to the synthesis methods of Examples 1 and 2 listed above, so they will not be described in detail here.
[0118] Device Example 1:
[0119] Organic electroluminescent devices were prepared using compound R003 prepared in Example 1 and compound H020 prepared in Example 2. Specifically, the preparation method of the organic electroluminescent device is as follows:
[0120] ITO anode: The 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). After drying, it was transferred to a plasma cleaner for 5 min to obtain the ITO anode.
[0121] HIL (Hole Injection Layer): 4,4',4''-tris(N-3-methylphenyl-N-phenylamino)triphenylamine is vacuum-deposited onto an ITO anode in a vapor deposition machine.
[0122] m-MTDATA) 200Å, forming a hole injection layer.
[0123] 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.
[0124] Emissive layer: The emissive layer comprises compound R003, compound H020, and a dopant. After forming a hole injection layer and a hole transport layer, the emissive layer is formed on the HTL: A first host compound and a second host compound are introduced as hosts into two chambers of a vacuum phase 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, with a doping amount of 3 wt% based on the total amount of host and dopant, to form an emissive layer with a thickness of 40 nm on the hole transport layer.
[0125] HBL (Hole Blocking Layer): A hole blocking layer is formed by vacuum evaporation of 100 Å of bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq) on the luminescent layer.
[0126] 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.
[0127] EIL (Electron Injection Layer): LiF2 10Å is vacuum-deposited on the electron transport layer to form the electron injection layer.
[0128] Cathode: 1500 Å of Al is deposited on the electron injection layer to form a cathode, i.e., an organic electroluminescent device is obtained.
[0129] Referring to the method for preparing organic electroluminescent devices provided in Device Example 1, another 58 organic electroluminescent compounds were selected to replace compound R003 and compound H020 for vapor deposition of the host material, so as to prepare organic electroluminescent devices of the corresponding compounds.
[0130] Red-light doped material (Z1):
[0131] .
[0132] The device fabrication processes of Device Examples 1-30, Comparative Examples 1-7 and Parallel Examples 1-6 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 specific parameters are shown in Table 1.
[0133] Table 1
[0134]
[0135] The comparative example structure is as follows:
[0136]
[0137] Performance testing: The driving voltage, luminous efficiency, and lifetime of the organic electroluminescent devices obtained in Comparative Examples 1-7, Parallel Examples 1-6, and Device Examples 1-30 were characterized at a brightness of 5000 nits. The test results are shown in Table 2 below.
[0138] Table 2
[0139]
[0140] As can be seen from Table 2, the driving voltage of the organic electroluminescent devices provided by Device Examples 1-30 and Parallel Examples 1-6 of the present invention is 2.77-4.95V, which is significantly lower than the driving voltage of Comparative Examples 1-7. At the same time, the luminous efficiency is higher than that of Comparative Examples 1-7, and the lifetime is significantly improved compared with Comparative Examples 1-7.
[0141] Therefore, it can be seen that, compared with organic electroluminescent devices prepared using comparative compounds E-1, E-2, E-3, F-1, F-2, and F-3 as dual host materials for the light-emitting layer, the organic electroluminescent device prepared using the organic electroluminescent compound provided by this invention as the light-emitting layer material has the following advantages: the structure of the first host material provided by this invention is naphthalene 2,3-naphthazole, which is more likely to undergo electrophilic substitution reaction under certain conditions, can form a smooth transition with the energy levels of other functional layers, reduces charge accumulation at the interface, and inhibits exciton quenching caused by molecular aggregation, thus significantly reducing the driving voltage and significantly improving the luminous efficiency. Furthermore, under high temperature and light irradiation, the structure of naphthalene 2,3-naphthazole is more stable than that of E-1, E-2, and E-3, making the prepared organic electroluminescent device less prone to deactivation during operation and extending its service life.
[0142] The above description of the disclosed embodiments enables those skilled in the art to make or use the invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the invention. Therefore, the invention is not to be limited to the embodiments shown herein, but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims
1. A main material, characterized in that, The main material has the following structure: 。 2. An organic electroluminescent material containing two main components, characterized in that, The organic electroluminescent material containing two hosts comprises the host material and the second host material as described in claim 1, and the mass ratio of the host material to the second host material is 1:99-99:1; the second host material has the structure shown in general formula 2: ; Wherein, D1 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl; D2 is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted benzophenanthryl; D3 is selected from substituted or unsubstituted C6-C30 aryl groups and substituted or unsubstituted C6-C24 heteroaryl groups; L4, L5, and L6 are each independently selected from the linking bond, phenyl, or naphthyl group; The heteroaryl group comprises a monocyclic aromatic group with at least one heteroatom, wherein the heteroatom is O, S, N, or P; The substituted or unsubstituted group in the "substituted or unsubstituted" designation is selected from deuterium, fluorine, C1-C10 alkyl, C3-C10 cycloalkyl, C3-C10 heterocycloalkyl, or the following groups: , The heteroatoms of the C3-C10 heterocyclic alkyl groups are selected from oxygen, nitrogen, and sulfur.
3. An organic electroluminescent material containing two main components, characterized in that, The organic electroluminescent material containing two main bodies comprises the main body material as described in claim 1 and a second main body material, wherein the mass ratio of the main body material to the second main body material is 1:99-99:1; the second main body material specifically has the following structure: 。 4. An organic electroluminescent device, characterized in that, The organic electroluminescent device comprises the organic electroluminescent material with a dual host as described in claim 2 or claim 3.
Citation Information
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