A quinolizine derivative and electroluminescent device thereof

Abstract

The application discloses a quinolizine derivative and an electroluminescent device thereof. The quinolizine derivative of the application converts the planar structure combination mode commonly used by traditional hole transport materials into a fixed three-dimensional combination mode through a spiro carbon, so that the fragments of the material are more consistent in spatial orientation, the hole injection and transmission of the device are integrated, the better electron blocking effect is considered, and the effective simplification of the device structure can be realized.

Description

Technical Field

[0001] This invention belongs to the field of organic light-emitting materials and semiconductor technology, specifically relating to a quinazine derivative and its electroluminescent device. Background Technology

[0002] With the further popularization and application of information technology, information display technology, as one of the important carriers of information, has made rapid progress in recent years. The industry is gradually maturing and stabilizing, providing a very user-friendly human-computer interface for information visualization in various electrical appliances, vehicles, and wearable devices. As a rising star, OLED display technology has made significant progress this century. To meet the stringent engineering requirements of thinness, transparency, wearability, foldability, low energy consumption, wide viewing angle, and low-temperature resistance, this technology is the most promising path to provide an integrated solution to these requirements. Currently, commercially available OLED displays are gradually expanding from small-screen applications to larger screens, flexible displays, and ultra-thin displays, and are expected to be the next generation of products that completely replace existing display technologies in the future. To further promote the application of this technology, industry practitioners are investing heavily in research and development across various aspects, from device design and engineering innovation to new material design, striving to meet people's multi-dimensional and human-centered display needs as soon as possible.

[0003] New materials, as a crucial driving force for innovation in display technology, have always been a top priority for researchers in this field. Currently, most mature and mainstream OLED display devices employ a sandwich-type multilayer structure, where each functional layer works synergistically to optimize the overall device's technical parameters. This multilayer structure primarily includes an anode plate, a cathode plate, and functional materials located between them. Specifically, functional layers such as a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer are sequentially filled between the anode and cathode plates. To effectively improve the luminous efficiency of the light-emitting device while reducing power consumption and extending its lifespan, the materials for each functional layer need continuous innovation and iteration to meet the latest market demands.

[0004] Currently, there are many types of hole transport materials on the market. However, most existing hole transport materials need to be used in conjunction with hole blocking materials, which makes the already complex multilayer device structure more complicated and introduces instability factors into the engineering implementation process. In order to simplify the device structure, devices fabricated using a material that can both realize hole injection and transport and effectively block electron penetration will have a relatively simple structure, resulting in improved device yield and luminescence stability. This avoids the hidden danger of increased device defect rate caused by instability factors due to complex structures.

[0005] To effectively simplify the device structure, reduce the complexity of the device process, improve the yield rate, and thus reduce manufacturing costs, while ensuring the stability of the device's light emission, significant research and development work is still needed in the design and development of the charge transport layer materials (hole transport materials and electron transport materials). This is also an important direction for the future development of such materials. Currently, there are few publicly available technologies that can achieve multifunctional hole transport materials. Therefore, developing a hole transport material that can both inject and transport holes and effectively block electron penetration has profound technological innovation value and broad market prospects. Summary of the Invention

[0006] The purpose of this invention is to overcome the shortcomings of the prior art and provide a quinazine derivative and its electroluminescent device, wherein the quinazine derivative is used as a hole transport material.

[0007] To solve the technical problem, the technical solution of the present invention is: a quinazonium derivative, wherein the structural formula of the quinazonium derivative includes formula 1, formula 2 and formula 3:

[0008]

[0009] R1, R2, and R3 are selected from H, D, cyano, halogen, and C1-C1 groups, respectively. 15 One of alkyl, aryl, or heterocyclic aromatic hydrocarbons; X is selected from O or S.

[0010] Preferably, general formula 1 includes chemical formulas 1 to 3, and the specific structural formulas are as follows:

[0011]

[0012] General formula 2 includes chemical formulas 4 to 6, and the specific structural formulas are as follows:

[0013]

[0014] General formula 3 includes chemical formulas 7 to 9, and the specific structural formulas are as follows:

[0015]

[0016] R1, R2, and R3 are independently selected from H, D, cyano, halogen, and C1-C1 groups, respectively. 15 One of alkyl, aryl, or heterocyclic aromatic hydrocarbons; X is selected from O or S.

[0017] Preferably, an electroluminescent device includes a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer contains any one or a combination of at least two of the compounds 1 to 120.

[0018] Preferably, the organic layer includes a hole transport layer, a light-emitting layer, and an electron transport layer; the first electrode and the second electrode are the cathode and the anode, respectively; the hole transport layer is located between the anode and the light-emitting layer; the electron transport layer is located between the cathode and the light-emitting layer; and the hole transport layer is selected from any one or a combination of at least two of compounds 1 to 120.

[0019] Preferably, the first electrode is formed by sputtering or deposition on a substrate. When the first electrode is used as an anode, it is selected from indium tin oxide, indium zinc oxide, tin dioxide, zinc oxide, or any combination thereof. When the first electrode is used as a cathode, it is selected from magnesium, silver, aluminum, aluminum-lithium, calcium, magnesium-indium, magnesium-silver metals or alloys, or any combination thereof.

[0020] Preferably, the light-emitting layer is made of a composite of a host light-emitting material and a guest light-emitting material; the host light-emitting material is selected from... One or a combination of two, wherein the guest luminescent material is selected from... Furthermore, the mass ratio of the primary luminescent material to the secondary luminescent material is 95:5.

[0021] Preferably, the material of the electron transport layer is selected from E1 or E2, and their structures are as follows:

[0022] Compared with the prior art, the advantages of the present invention are as follows:

[0023] (1) The quinazine derivative of the present invention transforms the planar structure combination mode commonly used in traditional hole transport materials into a fixed three-dimensional combination mode through helical carbon, making the spatial orientation of each segment of the material molecule more consistent, realizing the integration of hole injection and transport in the device, while taking into account a good electron blocking effect, and achieving effective simplification of device structure.

[0024] (2) The quinazine derivative of the present invention has a spatial cross-conformation, which ensures the formation of differentiated carrier conduction energy levels within the molecular structure, thereby forming different carrier conduction channels. This is beneficial for carrier injection and conduction between materials with different energy levels, and thus beneficial for obtaining the interface stability between the aromatic amine material and the adjacent material, thereby beneficial for obtaining good high and low temperature driving lifetime of the application device.

[0025] (3) The stereostable properties of the quinazine derivative of the present invention also make the glassy film formed by the material more stable, achieving maximum contact with the anode material and ensuring reliable and stable injection and transport of holes.

[0026] (4) The electroluminescent device of the present invention uses a nitrogen-containing fixed core structure such as quinazine to replace the conventional open triarylamine structure, which further enhances the consistency of the material in microstructure, and at the same time optimizes and improves the thermal stability of the material without increasing the molecular structure of the material. Attached Figure Description

[0027] Figure 1 A cross-sectional view of an electroluminescent device according to the present invention;

[0028] Figure 2 The NMR spectrum of compound 1 of the present invention;

[0029] Figure 3 The NMR spectrum of compound 29 of this invention;

[0030] Figure 4 The NMR spectrum of compound 52 of this invention;

[0031] Figure 5 The NMR spectrum of compound 108 of this invention;

[0032] Figure 6 The NMR spectrum of compound 118 of the present invention.

[0033] Appendix Figure 1 Marker explanation:

[0034] 1. Glass plate, 2. Anode layer, 3. Hole injection layer, 4. Hole transport layer, 5. Electron blocking layer, 6. Light emitting layer, 7. Hole blocking layer, 8. Electron transport layer, 9. Electron injection layer, 10. Cathode layer, 11. Cover layer. Detailed Implementation

[0035] The specific embodiments of the present invention are described below with reference to examples. The raw materials and reagents used in the present invention are all commercially available.

[0036] This invention discloses a quinazon derivative, wherein the general structural formula of the quinazon derivative includes general formula 1, general formula 2, general formula 3, general formula 4, general formula 5, general formula 6, general formula 7, general formula 8, general formula 9, general formula 1 ...

[0037] Formula 2 and General Formula 3:

[0038]

[0039] R1, R2, and R3 are independently selected from H, D, cyano, halogen, and C1-C1 groups, respectively. 15 One of alkyl, aryl, or heterocyclic aromatic hydrocarbons; X is selected from O or S.

[0040] Preferably, general formula 1 includes chemical formulas 1 to 3, and the specific structural formulas are as follows:

[0041]

[0042] General formula 2 includes chemical formulas 4 to 6, and the specific structural formulas are as follows:

[0043]

[0044] General formula 3 includes chemical formulas 7 to 9, and the specific structural formulas are as follows:

[0045]

[0046] R1, R2, and R3 are selected from H, D, cyano, halogen, and C1-C1 groups, respectively. 15 One of alkyl, aryl, or heterocyclic aromatic hydrocarbons; X is selected from O or S.

[0047] Preferably, the quinazonium derivative includes compounds 1 to 120, with the following specific structural formulas:

[0048]

[0049]

[0050]

[0051]

[0052]

[0053] Preferably, an electroluminescent device includes a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, wherein the organic layer contains any one or a combination of at least two of the compounds 1 to 120.

[0054] Preferably, the organic layer includes a hole transport layer, a light-emitting layer, and an electron transport layer; the first electrode and the second electrode are the cathode and the anode, respectively; the hole transport layer is located between the anode and the light-emitting layer; the electron transport layer is located between the cathode and the light-emitting layer; and the hole transport layer is selected from any one or a combination of at least two of compounds 1 to 120.

[0055] Preferably, the first electrode is formed by sputtering or deposition on a substrate. When the first electrode is used as an anode, it is selected from indium tin oxide, indium zinc oxide, tin dioxide, zinc oxide, or any combination thereof. When the first electrode is used as a cathode, it is selected from magnesium, silver, aluminum, aluminum-lithium, calcium, magnesium-indium, magnesium-silver metals or alloys, or any combination thereof.

[0056] Preferably, the light-emitting layer is made of a composite of a host light-emitting material and a guest light-emitting material; the host light-emitting material is selected from... One or a combination of two, wherein the guest luminescent material is selected from... Furthermore, the mass ratio of the primary luminescent material to the secondary luminescent material is 95:5.

[0057] Preferably, the material of the electron transport layer is selected from E1 or E2, and their structures are as follows:

[0058] The synthesis process of compounds 1-120 is described below:

[0059] The key intermediate synthesis process during implementation is as follows:

[0060] 1. Synthesis steps of key intermediate M1:

[0061]

[0062] Step 1:

[0063]

[0064] Procedure: Under argon protection, 279 g (3.0 mol) of 2-methylpyridine and 1.5 L of tetrahydrofuran were added sequentially to a 5 L three-necked flask. After stirring until homogeneous, the mixture was cooled to -78 °C, and 1.55 L (2 mol / L) of LDA was added dropwise. After reacting at this temperature for 1 h, 324 g (3.3 mol) of methyl 2-butynedoate was slowly added dropwise. After the addition was complete, the mixture was brought to room temperature, and the reaction was quenched with a small amount of water. The reaction was then complete. 1 L of water and 2.5 L of toluene were added to the reaction solution, and the mixture was stirred and separated. The organic phase was washed until neutral and then passed through a silica gel column to obtain a light yellow oily substance M1-1, weighing 406 g, with a GC content of 97% and a yield of 85%. GC-MS showed a molecular weight of 159.06.

[0065] Step Two:

[0066]

[0067] Procedure: Add 2.5 mol of M1-1 to a 3L three-necked flask and 1.5L of acetonitrile sequentially. Stir at room temperature for 0.5-1 hour until the starting material disappears, indicating the reaction is complete. Concentrate the reaction solution and evaporate to dryness to obtain a light yellow solid M1 weighing 390g. HPLC purity is 99%, yield is 98%, and GC-MS shows a molecular weight of 159.02.

[0068] 2. The synthesis steps of M2:

[0069]

[0070] Procedure: Under argon protection, 119 g (0.33 mol) of 2-iodo-2'-bromobiphenyl and 700 mL of THF were added to a 2000 mL three-necked flask. The mixture was stirred and cooled to -95℃ to -100℃. 170 mL of n-butyllithium (2.0 mol / L) was added dropwise to the system, and the reaction was maintained at -95℃ to -100℃ for 1 h. Then, 150 mL of M148 g (0.3 mol) THF solution was slowly added dropwise to the above system. After the addition was complete, the reaction was maintained at the above temperature for 0.5 h, and then naturally warmed to room temperature. 10 mL of water was added to quench the reaction, and the reaction was completed. The reaction solution was concentrated to dryness under reduced pressure, and 250 mL of toluene and 200 mL of water were added. After stirring, the mixture was washed with water and separated. The organic phase was washed with water again until neutral and then dried with anhydrous magnesium sulfate. The dried organic phase was filtered and collected, then transferred to another 500 mL three-necked flask. 58 g (0.6 mol) of methanesulfonic acid was slowly added dropwise with stirring. The reaction was continued at room temperature for 1–2 hours until complete. Then, 200 mL of water was added to quench the reaction. The organic phase was separated, washed repeatedly with small amounts of water until neutral, concentrated under reduced pressure to dryness, and then refluxed with 150 mL of n-heptane to disperse it. After cooling to room temperature, it was filtered and dried to obtain a white solid M2-1, weighing 82 g, with an HPLC purity of 99%, a yield of 73%, and an LC-MS molecular weight of 373.05.

[0071]

[0072] Procedure: Under argon protection, add M2-167g (0.18mol), benzophenone imine 36g (0.20mol), toluene 500mL, sodium tert-butoxide 35g (0.36mol) to a 1000mL three-necked flask in sequence. After gas replacement, add Pd2(dba) 30.83g (0.9mmol) and DPE-phos 0.97g (1.8mmol). Heat to reflux and react for 4-5 hours until the reaction is complete. After naturally cooling to room temperature, 250 mL of water was added, and the mixture was washed and separated. The organic phase was washed again with water until neutral. Then, 30 mL of concentrated hydrochloric acid was added, and the temperature was raised to 60–70 °C. The mixture was stirred thoroughly for 5 hours until a large amount of solid precipitated. The mixture was then cooled to room temperature, filtered, and dried. The solid was collected and added back to the reaction flask. 750 mL of 1 mol / L NaOH solution was added, and the temperature was raised to 70–80 °C. The mixture was stirred thoroughly for 10–12 hours, then cooled to room temperature, filtered, and dried to collect the crude solid. The crude solid was further purified by boiling and washing with a mixed solvent of toluene and ethanol to obtain a white solid M2, weighing 46 g, with an HPLC purity of 99% and a yield of 82%; the LC-MS molecular weight was 310.14.

[0073] 3. The synthesis steps of M3:

[0074]

[0075] Operating procedure: Following the M2-1 synthesis process, a total of 119g of 3-bromo-2'-iodobiphenyl was fed, yielding 90g of M3-1, with a yield of 80%; LC-MS molecular weight was 373.05.

[0076] M3 Synthesis:

[0077]

[0078] Operating procedure: Following the M2 synthesis process, a total of 167g of M3 was fed, and 47g of M3 was produced, with a yield of 85%; LC-MS molecular weight was 310.07.

[0079] 4. M4 synthesis steps:

[0080]

[0081] Operating procedure: Following the M2-1 synthesis process, a total of 119g of 4-bromo-2'-iodobiphenyl was fed, yielding 99g of M4-1, with a yield of 86%; LC-MS molecular weight was 373.01.

[0082]

[0083] Operating procedure: Following the M2 synthesis process, a total of 167g of M4 was fed, and 42g of M4 was produced, with a yield of 75%; LC-MS molecular weight was 310.11.

[0084] The synthesis process of the preferred compounds 1, 29, and 52 using the aforementioned key intermediates is illustrated below:

[0085] Synthesis of Compound 1:

[0086]

[0087] Procedure: Add 1.87 g of M2-1, 1.0 g of carbazole, 80 mL of xylene, 1.2 g of sodium tert-butoxide, 0.1 g of Pd2(dba)3, and 0.06 g of Amphos to a 250 mL three-necked flask. Heat to 120–125 °C under an inert atmosphere and react for 6–8 h until complete. Wash the reaction solution with water, dry it, and concentrate it under reduced pressure to obtain a crude product. Purify the crude product using silica gel column chromatography to obtain 1.75 g of pure product (76% yield). LC-MS showed a molecular weight of 460.15.

[0088] Synthesis of compound 29:

[0089]

[0090] Procedure: Add 1.87 g of M3-1, 1.10 g of phenoxazine, 80 mL of xylene, 1.2 g of sodium tert-butoxide, 0.1 g of Pd2(dba)3, and 0.06 g of Amphos to a 250 mL three-necked flask. Heat to 120–125 °C under an inert atmosphere and react for 6–8 h until complete. Wash the reaction solution with water, dry it, and concentrate it under reduced pressure to obtain a crude product. Purify the crude product using silica gel column chromatography to obtain 1.67 g of pure product (70% yield). LC-MS showed a molecular weight of 476.10.

[0091] Synthesis of compound 52:

[0092]

[0093] Procedure: Add 1.87 g M2, 1.28 g 4-bromobiphenyl, 80 mL toluene, 1.2 g sodium tert-butoxide, 0.1 g Pd2(dba)3, and 0.06 g Amphos to a 250 mL three-necked flask. Heat to 100–110 °C under an inert atmosphere and react for 6–8 h until complete. Wash the reaction solution with water, dry it, and concentrate it under reduced pressure to obtain a crude product. Purify the crude product using a silica gel column chromatography method to obtain 1.90 g of a white solid, yield 82%.

[0094]

[0095] Procedure: Compound 52-11.90 g, 4-bromo-tert-butylbenzene 1.05 g, toluene 80 mL, sodium tert-butoxide 1.0 g, Pd2(dba)3 0.1 g, and Amphos 0.06 g were added to a 250 mL three-necked flask. The mixture was heated to 120–125 °C under an inert atmosphere and reacted for 6–8 h until the reaction was complete. The reaction solution was washed with water, dried, and concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography to obtain 1.63 g of pure product, with a yield of 67%. LC-MS showed a molecular weight of 594.25.

[0096] Compounds 2 to 39 were synthesized using the same procedure as compound 1, and compounds 40 to 120 were synthesized using the same procedure as compound 52. The key intermediates used are listed in Tables 1 and 2 below.

[0097] Table 1

[0098]

[0099] (Note: Intermediates M2, M3, and M4 react with compound A1 to form compounds 1 to 3, respectively. Similarly, intermediates M2, M3, and M4 react with compounds A2 to A9 to form compounds 4 to 27, respectively. Intermediates M2, M3, and M4 react with compound B1 to form compounds 28 to 30, respectively. The products of the reactions of compounds A10 to A19 with intermediate M1 then react with compound B1 to form compounds 31 to 39 in sequence.)

[0100] Table 2

[0101]

[0102]

[0103] (Note: The brominated derivatives in column 1 react with intermediates M2, M3, and M4 to form compounds 40–57, respectively; the brominated derivatives in columns 2–5 react with intermediates M2, M3, and M4 to form compounds 58–120, respectively.)

[0104] Figures 2-6 The NMR spectra of compounds 1, 29, 52, 108, and 118 are shown.

[0105] Based on the preferred compounds 1-120 described above, these compounds are used as hole transport materials in test device samples. The basic structure and fabrication method of the device employ conventional device fabrication techniques. A schematic diagram of the device structure is shown below. Figure 1 As shown, the specific details of the device are as follows:

[0106] The experimental device comprises five main parts: an anode (ITO conductive glass), a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and a cathode. One or more combinations of the preferred compounds 1-120 are used in the hole transport layer (HTL) as a hole transport material for evaluation experiments. A brief description of the device fabrication process is as follows:

[0107] A substrate can be used below the first electrode or above the second electrode. The substrate is typically made of glass or polymer material with excellent mechanical strength, thermal stability, water resistance, and transparency. In this test, ITO conductive glass was used. Furthermore, the substrate can also be used as a display substrate to incorporate a thin-film transistor (TFT) array and a specific display image formed by combining these arrays.

[0108] The organic layer includes a hole transport layer, a light-emitting layer, and an electron transport layer. The first electrode and the second electrode are the anode and the cathode, respectively. The hole transport layer is located between the anode and the light-emitting layer, and the electron transport layer is located between the cathode and the light-emitting layer. The hole transport layer material is any one or more of the compounds 1 to 120 of the present invention. The host material and guest material used are common and excellent host materials and guest materials recognized in the industry and used for testing.

[0109] The first electrode can be formed by sputtering or deposition on a substrate. As the anode, the first electrode can be made of transparent conductive oxide materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin dioxide (SnO2), and zinc oxide (ZnO), or any combination thereof. Similarly, the second electrode, as the cathode, can be made of metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag), or organic combinations thereof.

[0110] The functional organic layer can be formed on the electrode by methods such as vacuum thermal evaporation, spin coating, or printing. The compound used as the organic layer can be a small organic molecule, a large organic molecule, a polymer, or a combination thereof.

[0111] The hole transport layer (HTL) can be a single-layer hole transport layer (containing only one compound that acts as both hole injection and hole transport) or a composite hole transport layer (containing multiple compounds). The composite hole transport layer is arranged in the order of hole injection layer (HIL), hole transport layer (HTL), and electron blocking layer (EBL), a common combination of organic hole materials in the industry. This application uses a single-layer structure model, and the hole transport layer material can be selected from any one or more combinations of compounds 1 to 120 of this invention. The luminescent layer is located between the hole transport layer and the electron transport layer. The main luminescent material is selected from one or a combination of two mature main luminescent materials BH-1 and BH-2, and the guest luminescent material used is a mature guest luminescent material used in the industry for matching tests. The main luminescent material and the guest material are used in a 95:5 ratio. After the functional layer for organic light emission is fabricated, an electron transport material is deposited onto the light-emitting layer. Following this deposition, a metal cathode is sputtered, and finally, the device is packaged using industry-standard device packaging methods. Samples used for testing are prepared as 30mm × 30mm specimens, and their various light emission performance indicators are tested. Compared to commonly used hole transport layer materials, the device exhibits more stable performance and superior lifetime.

[0112] Device Comparison Example 1:

[0113] Organic electroluminescent devices are prepared according to the following steps:

[0114] like Figure 1 As shown, the substrate layer 1 (glass plate) and the anode layer 2 (ITO conductive glass (1.5mm)) are washed sequentially, namely, by alkaline washing, pure water washing, drying, and then ultraviolet-ozone washing to remove organic residues on the surface of the anode layer. After the above washing, a 10nm thick HT-1:P-2 (dopant) = 95:5 film is deposited on the anode layer 2 using a vacuum evaporation apparatus as a hole injection layer 3. Then, a 117nm thick HT-1 film is deposited as a hole transport layer 4. Subsequently, a 10nm thick EB-1 film is deposited as an electron blocking layer 5. After the electron blocking materials are deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated, using BH-2 as the host light-emitting material and DB-1 as the guest light-emitting material. The guest light-emitting material has a doping weight ratio of 5%, and the light-emitting layer thickness is 20nm (BH-1:Ir(PPy)3 = 95:5 can also be used as the light-emitting layer material). Following the aforementioned light-emitting layer 6, HB1 is deposited to a thickness of 8 nm, serving as the hole-blocking layer 7. Above the hole-blocking layer 7, ET-1 and Liq are deposited at a mass ratio of 1:1, resulting in a vacuum-deposited film thickness of 30 nm; this layer serves as the electron transport layer 8. On the electron transport layer 8, a 1 nm thick LiF layer is fabricated using a vacuum evaporation apparatus; this layer serves as the electron injection layer 9. On the electron injection layer 9, a 16 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9; this layer serves as the cathode layer 10. On the cathode layer 10, a 70 nm thick CP-1 layer is vacuum-deposited as the capping layer 11. At this point, the fabrication of all functional layers of the device is complete. Finally, the multilayer structure is vacuum-encapsulated, completing the entire fabrication process of the evaluation device.

[0115] The hole transport material used as the control test device is a traditional hole transport material. The hole transport materials used in the device comparison examples 1 to 3 are HT-1, HT-2, and HT-3, respectively.

[0116] Examples of hole injection layer and hole transport layer

[0117] Examples 1 to 10:

[0118] The method was carried out according to Comparative Example 1, except that the organic materials in the hole injection layer and the hole transport layer were replaced with compounds 1, 5, 16, 29, 52, 73, 89, 55, 108, 112, 118, and 120 of the present invention, respectively.

[0119] An embodiment integrating the hole injection layer and the hole transport layer.

[0120] Examples 11 and 12:

[0121] Compound 118 (Example 11) and Compound 120 (Example 12) were used as both hole injection layer materials and hole transport layer materials.

[0122] The experimental design described above is shown in Table 3 below:

[0123] Table 3

[0124]

[0125] (Note: "X" represents compounds 1, 5, 16, 29, 52, 73, 89, 55, 108, 112, 118, and 120, respectively; "Y" represents compounds 118 and 120, respectively.)

[0126] The functional layer material structure involved in the fabrication process of the above-mentioned device is as follows:

[0127]

[0128] The multilayer composite structure testing device and control device prepared using the compounds of the present invention are detailed in Table 4 below, along with their detection data.

[0129] Table 4

[0130]

[0131]

[0132] As shown in Table 4, based on the device test data, under the same fabrication process conditions during the testing period, the test devices prepared using the preferred compounds of this invention as hole injection and transport materials generally exhibit significantly improved carrier transport rates compared to traditional hole transport materials HT-1, HT-2, and HT-3. The device efficiency and lifetime are effectively improved, especially the high-temperature lifetime. Furthermore, even when the preferred compounds of this invention completely replace the traditional combination mode of hole injection and transport materials, and are converted into a single-layer mode, the test devices still demonstrate excellent performance in all data indicators, achieving the effect of simplifying and unifying the core structure.

[0133] The quinomozine derivative of this invention transforms the planar structure combination commonly used in traditional hole transport materials into a fixed three-dimensional combination mode through helical carbon, making the spatial orientation of each segment of the material more consistent, realizing the integration of hole injection and transport in the device, while taking into account a good electron blocking effect, and achieving effective simplification of device structure.

[0134] The quinazine derivatives of this invention have a spatial cross-conformation, which ensures the formation of differentiated carrier conduction energy levels within the molecular structure, thereby forming different carrier conduction channels. This is beneficial for carrier injection and conduction between materials with different energy levels, and thus beneficial for obtaining the interfacial stability between the aromatic amine material and the adjacent material, thereby benefiting the application device to obtain good high and low temperature driving lifetime.

[0135] The steric stability of the quinazonium derivative of this invention also makes the glassy film formed by the material more stable, achieving maximum contact stability with the anode material and ensuring reliable and stable hole injection and transport.

[0136] The electroluminescent device of this invention uses a nitrogen-containing fixed core structure such as quinazine to replace the conventional open triarylamine structure, which further enhances the consistency of the material's microstructure. At the same time, the thermal stability of the material is also improved and optimized without increasing the molecular structure of the material.

[0137] The preferred embodiments of the present invention have been described in detail above. However, the present invention is not limited to the above embodiments. Within the scope of knowledge possessed by those skilled in the art, various changes can be made without departing from the spirit of the present invention.

[0138] Many other changes and modifications can be made without departing from the concept and scope of this invention. It should be understood that this invention is not limited to the specific embodiments, and the scope of this invention is defined by the appended claims.

Claims

1. A quinazon derivative, characterized in that, The quinazon derivatives are selected from compounds 1 to 120; 。 2. An electroluminescent device, comprising a first electrode, a second electrode, and an organic layer located between the first electrode and the second electrode, characterized in that, The organic layer contains any one or a combination of at least two of the compounds 1 to 120 of claim 1.

3. The electroluminescent device according to claim 2, characterized in that: The organic layer includes a hole transport layer, a light-emitting layer, and an electron transport layer; the first electrode and the second electrode are a cathode and an anode, respectively; the hole transport layer is located between the anode and the light-emitting layer; the electron transport layer is located between the cathode and the light-emitting layer; and the hole transport layer is selected from any one or a combination of at least two of the compounds 1 to 120.

4. The electroluminescent device according to claim 3, characterized in that, The first electrode is formed by sputtering or deposition on a substrate. When the first electrode is used as an anode, it is selected from indium tin oxide, indium zinc oxide, tin dioxide, zinc oxide, or any combination thereof. When the first electrode is used as a cathode, it is selected from magnesium, silver, aluminum, aluminum-lithium, calcium, magnesium-indium, magnesium-silver metals or alloys, or any combination thereof.

5. An electroluminescent device according to claim 3, characterized in that: The light-emitting layer is composed of a host light-emitting material and a guest light-emitting material; the host light-emitting material is selected from... , One or a combination of two, wherein the guest luminescent material is selected from... or Furthermore, the mass ratio of the primary luminescent material to the secondary luminescent material is 95:

5.

6. An electroluminescent device according to claim 3, characterized in that: The electron transport layer is made of either E1 or E2, and its structures are as follows: , .

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