A macrocyclic twisted molecule and electroluminescent device

Abstract

The application discloses a large conjugated twisted molecule and an electroluminescent device, the microstructure of the molecule is reformed by introducing a planar structure into a twisted spiro carbon molecule to adjust the twisted posture of the molecule, the conjugation of the molecule is improved, the rigidity of the molecule is increased, and the symmetry of the molecule is reduced; the electroluminescent device made of the large conjugated twisted molecule has a reduced driving voltage, the luminous brightness is obviously improved, the overall device efficiency is effectively improved, and the device life is better than that of a traditional material device.

Description

Technical Field

[0001] This invention belongs to the field of organic light-emitting materials technology, specifically relating to a large conjugated twisted molecule and an electroluminescent device. Background Technology

[0002] In the emerging field of display technology, OLED display technology is maturing and gradually being widely adopted. Given its wide range of applications, the market is constantly placing new demands on the luminescent performance of these devices. As OLED light-emitting devices, their core elements are the device fabrication process and the luminescent materials used to achieve light emission. With continuous industry updates and iterations, the fabrication process has undergone continuous practical testing and refinement, resulting in increasingly stable and mature parameters and process conditions. This has led to continuously improving yield rates, thereby ensuring the cost and stability of the devices. However, the development and application of luminescent materials, another core element, is not as straightforward as updating and iterating process conditions. Selecting a luminescent material that offers superior luminescent performance, pure colorimetry, and a long lifespan is a challenging yet commercially valuable task. Currently, most OLED devices employ a multi-layered functional core approach, with functional layers primarily consisting of hole injection layers, hole transport layers, hole blocking layers, electron injection layers, electron transport layers, electron blocking layers, and luminescent layers. The luminescent layer is the most crucial element in determining the quality of a device. For the host luminescent material to achieve stable luminescence, it generally needs to possess a high LOMO energy level and a low HOMO energy level. This allows the molecules to have a larger energy system, enabling more efficient energy transfer for guest molecules. This achieves efficient luminescence from guest molecules while avoiding exciton annihilation due to excessively high concentrations of guest molecules. However, host luminescent molecules with a large energy system are relatively scarce in the current field of host luminescent materials, representing a significant performance indicator that needs to be overcome. Therefore, developing a novel host luminescent material holds great market potential. Summary of the Invention

[0003] The purpose of this invention is to overcome the shortcomings of the prior art and provide a large conjugated twisted molecule and an electroluminescent device, wherein the large conjugated twisted molecule is used as the main light-emitting material of the electroluminescent device.

[0004] To solve the technical problem, the technical solution of the present invention is: a large conjugated twisted molecule, wherein the general structural formula of the twisted molecule includes general formula 1, general formula 2 and general formula 3:

[0005]

[0006] Where Z1 to Z8 represent C or CH, and R1 and R2 are selected from H, D, cyano, halogen, and C1 to C2, respectively. 15One of alkyl, aryl, or heterocyclic aromatic hydrocarbons; X is selected from O or S; Y is selected from CH2, O, or S.

[0007] Preferably, the general formula 1 includes:

[0008]

[0009] General formula 2 includes:

[0010]

[0011] The general formula 3 includes:

[0012]

[0013] R1 and R2 are selected from H, D, cyano, halogen, and C1-C2, respectively. 15 It is one of alkyl, aryl, or heterocyclic aromatic hydrocarbons, where X is selected from O or S; and Y is selected from CH2, O, or S.

[0014] 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 169.

[0015] 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, and the electron transport layer is located between the cathode and the light-emitting layer. The main light-emitting material of the light-emitting layer is selected from, but is not limited to, any one or a combination of at least two of compounds 1 to 169.

[0016] 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, and 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, and any combination thereof.

[0017] 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 any one or a combination of at least two of compounds 1 to 169, and the weight ratio of the host light-emitting material to the guest light-emitting material is 90:10 to 95:5.

[0018] Preferably, the guest luminescent material is selected from Ir(PPy)3 or DB-1.

[0019] Compared with the prior art, the advantages of the present invention are:

[0020] (1) This invention adjusts the twisted posture of the molecule by introducing a planar structure into the twisted spirocarbon molecule, thereby achieving microscopic modification of the molecule, enhancing the conjugation of the molecule, increasing the rigidity of the molecule, and reducing the symmetry of the molecule, thereby raising the LOMO energy level of the molecule and lowering the HOMO energy level of the molecule, thus giving the molecule a larger energy system.

[0021] (2) The electroluminescent device made of the large conjugated twisted molecules of the present invention has a lower driving voltage, significantly improved luminous brightness, and effectively improved overall device efficiency. Moreover, the device life is better than that of traditional material devices.

[0022] (3) The large conjugated twisted molecule of the present invention is used as the main light-emitting material of electroluminescent device. Compared with traditional main light-emitting materials, its applicability is superior and its performance is excellent. Attached Figure Description

[0023] Figure 1 The NMR spectrum of compound 1 of the present invention; Figure 2 1. The NMR spectrum of compound 2 of the present invention;

[0024] Figure 3 The NMR spectrum of compound 17 of this invention; Figure 4 The NMR spectrum of compound 21 of the present invention;

[0025] Figure 5 The NMR spectrum of compound 31 of the present invention; Figure 6 The NMR spectrum of compound 37 of this invention;

[0026] Figure 7 The NMR spectrum of compound 128 of this invention; Figure 8 A schematic diagram of the structure of the electroluminescent device of the present invention.

[0027] Explanation of reference numerals in the attached figures:

[0028] 1. First electrode, 2. Second electrode, 3. Hole transport layer, 4. Light-emitting layer, 5. Electron transport layer. Detailed Implementation

[0029] The specific embodiments of the present invention are described below with reference to the accompanying drawings. The raw materials and reagents used in the present invention are all commercially available.

[0030] This invention discloses a large conjugated twisted molecule, the general structural formulas of which include general formula 1, general formula 2 and general formula 3:

[0031]

[0032] Where Z1 to Z8 represent C or CH, and R1 and R2 are selected from H, D, cyano, halogen, and C1 to C2, respectively. 15One of alkyl, aryl, or heterocyclic aromatic hydrocarbons; X is selected from O or S; Y is selected from CH2, O, or S.

[0033] Preferably, the general formula 1 includes:

[0034]

[0035] The general formula 2 includes:

[0036]

[0037] Formula 3 includes:

[0038]

[0039] R1 and R2 are selected from H, D, cyano, halogen, and C1-C2, respectively. 15 It is one of alkyl, aryl, or heterocyclic aromatic hydrocarbons, where X is selected from O or S; and Y is selected from CH2, O, or S.

[0040] Preferably, the twisted molecule comprises compounds 1 to 169, with the following specific structural formulas:

[0041]

[0042]

[0043]

[0044]

[0045]

[0046] 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 169 described above.

[0047] 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, and the electron transport layer is located between the cathode and the light-emitting layer. The main light-emitting material of the light-emitting layer is selected from, but is not limited to, any one or a combination of at least two of compounds 1 to 169.

[0048] 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, and 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, and any combination thereof.

[0049] 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 any one or a combination of at least two of compounds 1 to 169, and the weight ratio of the host light-emitting material to the guest light-emitting material is 90:10 to 95:5.

[0050] Preferably, the guest luminescent material is selected from Ir(PPy)3 or DB-1.

[0051] The synthesis process of compounds 1-169 is described below:

[0052] Example 1

[0053] Key intermediate M1 synthesis steps:

[0054] Step 1:

[0055]

[0056] Procedure: In a 5L three-necked flask, 172g (1.0mol) of 1-naphthoic acid, 362g (1.0mol) of 2,6-dibromoiodobenzene, and 1.5L of toluene were added sequentially. The mixture was stirred until dissolved, then 250mL of 8mol / L potassium hydroxide solution was added. After argon purging, 5.8g of tetraphenylphosphine palladium was added. The temperature was raised to 90–92℃ and maintained for 6–8 hours until the 1-naphthoic acid reacted completely. The reaction was then cooled to room temperature, and 1L of water was added. After stirring, the mixture was separated, and the organic phase was washed until neutral. The solution was then passed through a silica gel column. The column liquid was collected, concentrated under reduced pressure, and dried to obtain a crude solid. This crude solid was then slurried with 500mL of ethanol, filtered, and dried to obtain a white solid M1-1, weighing 304g, with a GC content of 97% and a yield of 84%.

[0057] Step 2:

[0058]

[0059] Procedure: 109 g (0.3 mol) of M1-1 and 1 L of THF were added to a 2 L three-necked flask. After dissolution, the mixture was cooled to -90 to -100 °C under argon protection. A 0.3 mol n-butyllithium solution was added dropwise, and the mixture was kept at -90 to -100 °C for 1 h. Then, 52 g of dry ice powder was added all at once, and the reaction was completed. The reaction solution was directly heated to room temperature and concentrated to dryness under reduced pressure. Then, it was acidified in 1 mol / L acid water to obtain a crude solid. The crude solid was further purified by boiling and washing with toluene to obtain a white solid with a weight of 74.5 g and a yield of 76%.

[0060] Step 3:

[0061]

[0062] Procedure: Under inert gas protection, add 200g of PPA to a 1L three-necked flask, heat to 130℃~140℃, and start stirring. Add 70g of M1-2 in batches, maintaining the internal temperature at 130℃~140℃. After the addition is complete, continue to keep the reaction at this temperature for 3~4 hours until the reactants are completely removed, indicating the reaction is complete. When the reaction solution is cooled to 80~85℃, carefully pour it into a large amount of ice water, filter to precipitate the solid, and further dissolve the crude solid in toluene for column purification and recrystallization to obtain 46g of a light yellow solid product, with a yield of 69%.

[0063] Step 4:

[0064]

[0065] Procedure: Under inert gas protection, 37g of 2-bromodiphenyl ether and 350mL of THF were added to a 3L three-necked flask. After stirring until dissolved, the mixture was cooled to -80 to -90℃. 75mL of n-butyllithium solution (2.0mol / L) was added dropwise, and the mixture was kept at this temperature for 1 hour. Then, 1.0L of THF solution dissolving 31g of M1-3 was added dropwise, maintaining the temperature at -80 to -90℃ throughout the process. After the addition was complete, the mixture was allowed to warm to room temperature naturally. A small amount of water was added to quench the reaction, and the reaction was then complete. The reaction solution was concentrated under reduced pressure and extracted with ethyl acetate. The aqueous solution was then concentrated to dryness under reduced pressure to obtain a crude product. The crude product was crystallized from ethanol to obtain 32g of a white product, with a yield of 67%.

[0066] Step 5:

[0067]

[0068] Procedure: Under inert gas protection, 30g of M1-4 and 300mL of dichloroethane solution were added to a 1L three-necked flask. After dissolving and clarifying the solution, the temperature was raised to 45-50℃, and 12g of p-toluenesulfonic acid was added. The mixture was then heated to reflux and the reaction continued for 2 hours until M1-4 was completely dissolved. The reaction solution was then diluted with water, separated, and the organic phase was washed with water and concentrated under reduced pressure. Recrystallization from toluene yielded a white solid product weighing 24g, with a yield of 83%.

[0069] Example 2

[0070] Key intermediate M2 synthesis steps:

[0071] Step 1:

[0072]

[0073] Procedure: Under inert gas protection, 40g of 2-bromodiphenyl sulfide and 400mL of THF were added to a 3L three-necked flask. After stirring until dissolved, the temperature was lowered to -80 to -90℃. 75mL of n-butyllithium solution (2.0mol / L) was added dropwise, and the mixture was kept at this temperature for 1 hour. Then, 1.0L of THF solution dissolving 31g of M1-3 was added dropwise, maintaining the temperature at -80 to -90℃ throughout the process. After the addition was complete, the mixture was allowed to warm to room temperature naturally. A small amount of water was added to quench the reaction, and the reaction was then complete. The reaction solution was concentrated under reduced pressure and extracted with ethyl acetate. The aqueous solution was then concentrated to dryness under reduced pressure to obtain a crude product. The crude product was crystallized from ethanol to obtain 31g of a white product, with a yield of 63%.

[0074] Step 2:

[0075]

[0076] Procedure: Under inert gas protection, 30g of M2-1 and 300mL of dichloroethane solution were added to a 1L three-necked flask. After dissolving and clarifying the solution, the temperature was raised to 45-50℃, and 12g of p-toluenesulfonic acid was added. The mixture was then heated to reflux and the reaction continued for 2 hours until M2-1 was completely dissolved. The reaction solution was then diluted with water, separated, and the organic phase was washed with water and concentrated under reduced pressure. Recrystallization from toluene yielded a pale yellow solid product weighing 22g, with a yield of 76%.

[0077] Example 3

[0078] Key intermediate M3 synthesis steps:

[0079] first step:

[0080]

[0081] Procedure: Under inert gas protection, 86g of 1-naphthoic acid, 170g of methyl 2-iodo-4-bromobenzoate, 600mL of toluene, and 400mL of ethanol were added to a 2L three-piece flask. The mixture was stirred and started to allow the solids to dissolve completely. Then, 138g of potassium carbonate and 200L of deionized water were added. The temperature was raised to 50–55℃, and 2.9g of tetraphenylphosphine palladium was added. The temperature was further raised to reflux for 10–12 hours until the reaction was complete. The reaction solution was separated, washed with water, and the organic phase was concentrated to dryness after passing through a silica gel column. Heptane was added to crystallize, yielding 133g of a light yellow solid product (78% yield).

[0082] Step Two:

[0083]

[0084] Procedure: Add 68g of M3-1, 400mL of ethanol, and 100mL of 10mol / L sodium hydroxide aqueous solution to a three-piece flask. Then, heat to reflux and react for 2-3 hours until the reaction of the raw material M3-1 is complete. Concentrate the reaction solution directly to dryness under negative pressure, then extract with ethyl acetate. During extraction, acidify the system with hydrochloric acid to pH < 2. Wash the organic phase with water until neutral, then concentrate to dryness under reduced pressure. Crystallize with petroleum ether to obtain 62g of white solid product, yield 95%.

[0085] Step 3:

[0086]

[0087] Operation process: Following the M1-3 synthesis feeding process, a total of 60g of M3-2 was fed, and 43g of M3-3 was produced, with a yield of 75%.

[0088] Step 4:

[0089]

[0090] Operation process: Following the M1-4 synthesis process, a total of 40g of M3-3 was fed, and 54g of M3-4 was produced, with a yield of 84%.

[0091] Step 5:

[0092]

[0093] Operation process: Following the M1 synthesis process, a total of 40g of M3-4 was fed, yielding 32g, with a yield of 83%.

[0094] Example 4

[0095] Key intermediate M4 synthesis steps:

[0096] first step:

[0097]

[0098] Operation process: Following the synthesis process of M2-1, 40g of 2-bromodiphenyl sulfide and 31g of M3-3 were fed respectively, and 33g of M4-1 was produced, with a yield of 67%.

[0099] Step Two:

[0100]

[0101] Operation process: Referring to the M2 synthesis process, 30g of M4-1 was fed in, and 23g of M4 was produced, with a yield of 79%.

[0102] Example 5

[0103] Key intermediate M4 synthesis steps:

[0104] first step:

[0105]

[0106] Operation process: Following the M3-1 synthesis process, 150g of methyl 2-iodo-5-bromobenzoate was fed, and 122g of M5-1 was produced, with a yield of 84%.

[0107] Step Two:

[0108]

[0109] Operation process: Referring to the M3-2 synthesis process, 120g of M5-1 was fed, and 107g of M5-2 was produced, with a yield of 93%.

[0110] Step 3:

[0111]

[0112] Operation procedure: Following the M1-3 synthesis process, 80g of M5-2 was fed, yielding 54g of M5-3, with a yield of 72%.

[0113] Step 4:

[0114]

[0115] Operation process: Referring to the M1-4 synthesis process, 50g of M5-3 was fed, and 47g of M5-4 was produced, with a yield of 61%.

[0116] Step 5:

[0117]

[0118] Operation process: Referring to the M1 synthesis process, 45g of M5-4 was fed in, and 37g of M5 was produced, with a yield of 86%.

[0119] Example 6

[0120] Key intermediate M6 synthesis steps:

[0121] first step:

[0122]

[0123] Procedure: Following the M2-1 synthesis process, 40g of 2-bromodiphenyl sulfide and 31g of M5-3 were fed, yielding 29g of M6-1, with a yield of 58%.

[0124] Step Two:

[0125]

[0126] Operation process: Referring to the M2 synthesis process, 25g of M6-1 was fed in, and 19g of M6 was produced, with a yield of 79%.

[0127] Example 7

[0128] Key intermediate M7 synthesis steps:

[0129] first step:

[0130]

[0131] Operation process: Following the M3-1 synthesis process, a total of 200g of methyl 2-iodo-5-bromobenzoate was fed, and 137g of M7-1 was produced, with a yield of 68%.

[0132] Step Two:

[0133]

[0134] Operation process: Following the M3-2 synthesis process, a total of 90g of M7-1 was fed, and 77g of M7-2 was produced, with a yield of 89%.

[0135] Step 3:

[0136]

[0137] Operation process: Following the synthesis of M1-3, a total of 60g of M7-2 was fed, and 31g of M7-3 was produced, with a yield of 55%.

[0138] Step 4:

[0139]

[0140] Operation process: Following the synthesis of M1-4, a total of 40g of M7-3 was fed, and 32g of M7-4 was produced, with a yield of 52%.

[0141] Step 5:

[0142]

[0143] Operation process: Referring to the M1 synthesis process, a total of 30g of M7-4 was fed, and 21g of M7 was produced, with a yield of 72%.

[0144] Example 8

[0145] Key intermediate M8 synthesis steps:

[0146] first step:

[0147]

[0148] Operation process: Referring to the synthesis process of M2-1, 30g of M7-3 was fed in, and 30.3g of M8-1 was produced, with a yield of 63%.

[0149] Step Two:

[0150]

[0151] Operation process: Referring to the M2 synthesis process, a total of 30g of M8-1 was fed, and 20.5g of M8 was produced, with a yield of 71%.

[0152] Examples of the synthesis processes for the preferred compounds of chemical formulas 1, 3, and 5 are as follows:

[0153] Synthesis of Compound 1:

[0154] Step 1:

[0155]

[0156] Procedure: Under an inert atmosphere, add 23.1 g of M1, 14.0 g of pinacol diboronate, 9.6 g of potassium acetate, and 200 mL of 1,4-dioxane to a 500 mL three-necked flask. After stirring, heat to 60–65 °C, then add 0.36 g of Pd(dppf)Cl2. Continue heating to reflux for 6–8 h until M1 reacts completely. Filter the reaction solution directly, collect the filtrate, concentrate to dryness under reduced pressure, dissolve in 500 mL of toluene, wash with water, pass the organic phase through a silica gel column, concentrate again under reduced pressure until solid precipitates, then stop. Cool to 10–15 °C, crystallize, filter, and dry to obtain 20.1 g of white solid A1 intermediate, yield 79%.

[0157] Step 2:

[0158]

[0159] Procedure: Under an inert atmosphere, add 5.0 g of Al, 2.8 g of 2-(2-bromophenyl)-6-chloroaniline, 75 mL of 1,4-dioxane, 2.7 g of potassium carbonate, 10 mL of deionized water, and 40.12 g of Pd(PPh3) to a 250 mL three-necked flask. Heat the system to reflux and react for 15–18 h until the reaction is complete. Wash the reaction solution with water and separate the liquids. Pass the organic phase through a diatomaceous earth funnel and collect the filtrate. Concentrate under reduced pressure to dryness to obtain a crude solid product. Add 25 mL of ethanol to disperse and slurry, then filter to obtain 4.1 g of A2 (yield 71%).

[0160] Step 3:

[0161]

[0162] Procedure: Add 4.1 g of A2 and 100 mL of THF to a 250 mL three-necked flask. Heat the system to 50–55 °C, add 1–2 drops of acetic acid, and then carefully add 1.2 g of tert-butyl nitrite dropwise. Maintain the reaction at 50–55 °C with stirring for 1.5–2 hours. Monitor the reaction by TLC until A2 is completely reacted. After the reaction is complete, concentrate the reaction solution under reduced pressure to dryness, then dissolve it again in toluene. Purify by silica gel column chromatography and crystallize from ethyl acetate to obtain 3.1 g of white solid product, yield 77%.

[0163] Step 4:

[0164]

[0165] Procedure: Add 3.0 g of A3, 1.0 g of diphenylamine, 90 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 2.74 g of pure product (74% yield). LC-MS showed a molecular weight of 699.25.

[0166] like Figure 1 The image shown is the NMR spectrum of product compound 1.

[0167] Synthesis of compound 113:

[0168]

[0169] The operation process is as follows:

[0170] Under an inert atmosphere, 3.0 g of A3, 0.98 g of carbazole, 1.2 g of sodium tert-butoxide, 0.1 g of Pd2(dba)3, and 0.06 g of Amphos were added to a 250 mL three-necked flask. The mixture was heated to reflux and kept at that temperature for 30–36 h until the reaction was complete. After the reaction was complete, the mixture was cooled to room temperature, dissolved in 300 mL of toluene, and then washed with water until neutral. The organic phase was concentrated to dryness under reduced pressure and purified by silica gel column chromatography to obtain 2.2 g of pure product, with a yield of 59.6%. LC-MS showed a molecular weight of 697.26.

[0171] Synthesis of compound 141:

[0172]

[0173] Under an inert atmosphere, 3.0 g of A3, 1.1 g of phenoxazine, 1.2 g of sodium tert-butoxide (60 mL diethylbenzene), 0.1 g of Pd2(dba)3, and 0.06 g of Amphos were added to a 250 mL three-necked flask. The mixture was heated to reflux and kept at that temperature for 18–24 h until the reaction was complete. After the reaction was complete, the mixture was cooled to room temperature, dissolved in 250 mL of toluene, and then washed with water until neutral. The organic phase was concentrated to dryness under reduced pressure and purified by silica gel column chromatography to obtain 2.5 g of pure product, with a yield of 66.2%. LC-MS showed a molecular weight of 713.21.

[0174] Examples of the synthesis processes for preferred compounds of chemical formulas 2, 4, and 6 are as follows:

[0175] Compound 65:

[0176] Step 1:

[0177]

[0178] The synthesis process was carried out in accordance with the A2 synthesis process.

[0179] Step 2:

[0180]

[0181] The synthesis process was carried out in accordance with the A3 synthesis process.

[0182] Step 3:

[0183]

[0184] The synthesis process was carried out following the same procedure as that for compound 1.

[0185] Compound 117 was synthesized following the same procedure as compound 113; compound 145 was synthesized following the same procedure as compound 141. The synthesis of other compounds followed similar methods, and the key intermediates used are summarized in Tables 1 and 2 below.

[0186]

[0187]

[0188] Table 1 Table 2

[0189]

[0190]

[0191] like Figures 2-7 The NMR spectra of compounds 2, 17, 21, 31, 37 and 128 are shown below.

[0192] The preferred compounds described in compounds 1 to 169 above were used as the main luminescent materials in the test device samples. The basic structure and fabrication method of the device adopted currently recognized device fabrication technology. A schematic diagram of the device structure is shown below. Figure 8 As shown, the specific details of the device are as follows:

[0193] The experimental device comprises five main parts: an anode (ITO conductive glass), a hole injection transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and a cathode. One or more of the aforementioned preferred compounds are used in the EML region as the primary luminescent material for the evaluation experiment. A brief description of the device fabrication process is as follows:

[0194] Preferably, a substrate can be used below the first electrode or above the second electrode. The substrate is 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 used for a display can also have a thin-film transistor (TFT) array and a specific display image formed by combining the arrays.

[0195] 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 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 main light-emitting material of the light-emitting layer is any one or more of the compounds 1 to 169 of the present invention, and the guest material used is a commonly recognized and excellent guest material used in conjunction with it.

[0196] Specifically, the first electrode can be formed by sputtering or depositing the material used as the first electrode on a substrate. The first electrode, serving as the anode, can be selected from 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, serving as the cathode, can be implemented using 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.

[0197] 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.

[0198] The hole transport layer can be a single-layer hole transport layer (HTL), including single-layer hole transport layers containing only one compound that acts as both hole injection and hole transport, and composite hole transport layers containing multiple compounds. Composite hole transport layers primarily consist of organic hole material combinations arranged in an industry-standard sequence, including a hole injection layer (HIL), a hole transport layer (HTL), and an electron blocking layer (EBL). The luminescent layer is located between the hole transport layer and the electron transport layer. The main luminescent material is selected from one or more combinations of compounds 1 to 169 (preferred). The guest luminescent material used in conjunction is a mature guest luminescent material that undergoes matching testing. The main luminescent material and the guest material are used in a ratio ranging from 90:10 to 95:5. After the functional layer for organic light emission is prepared, an electron transport material is deposited on the light-emitting layer. After the electron transport material is deposited, a metal cathode is sputtered. Finally, the device is packaged using industry-standard packaging methods. The sample used for testing is prepared as a 30mm×30mm sample. The light emission performance indicators of the sample are then tested and compared with the performance of commonly used host light-emitting materials. The test results show that the device exhibits superior light emission performance compared to conventional host light-emitting materials.

[0199] Application Example 1

[0200] The details are as follows:

[0201] Fabrication of the anode for the evaluation device: Anodes with a thickness of [missing information] are prepared. ITO glass substrates were cut to dimensions of 30mm × 30mm × 1mm and fabricated into experimental substrates with cathode, anode, and insulating layer patterns using conventional photolithography. The substrate surface was then sequentially textured using ultraviolet ozone and nitrogen-oxygen plasma gases to enhance the fine texture structure and remove dust or contaminants, thereby improving the work function of the anode substrate. After the pretreatment process, the experimental substrate (anode) was placed in a vacuum chamber and F4TCNQ or HATC, or a mixture thereof, was vacuum-deposited using a vertical evaporation method. A thick film is formed to create a hole injection layer (HIL) for the test device, followed by the deposition of NPD, FFD, or 2-TNATA as a hole transport layer. The film thickness is controlled within [specific parameters]. The hole injection layer and the hole transport layer together constitute the hole transport functional layer. A light-emitting layer is then deposited on the hole transport layer. The host light-emitting material of the light-emitting layer is one or more combinations of the aforementioned preferred compounds 1-169. During the deposition of the light-emitting layer, 3%-5% of Ir(PPy)3 or BD-1 (Rubrene or CDJTB can also be used) is doped into it as a guest light-emitting material for co-deposition. The thickness of the light-emitting layer is controlled within [specific parameters]. The EML luminescent functional layer is formed during testing. Then, a hole-blocking layer, TPBI or TAZ, is deposited on the luminescent layer, with a thickness of [insert thickness here]. BpyOXD or ET-205 thickness continues to be deposited on the hole blocking layer. Then, continue with the co-evaporation deposition of a LiQ:ET-205 or LiQ:BpyOXD5 layer at a weight ratio of 1:1, with a thickness of... The composite structure of the above three layers together forms the electron transport layer (ETL); then another layer is deposited on the ETL layer. Yb, and then an alloy layer with a Mg:Ag ratio of 1:9 is further deposited on top of the Yb layer by sputtering, with the thickness controlled at [thickness value missing]. The aforementioned two-layer composite structure forms the electron injection layer; the electron transport layer and the electron injection layer together form the electron transport functional layer of the test device. At this point, the fabrication of all functional layers of the device is complete. Finally, the multilayer structure is vacuum-sealed, completing the entire fabrication process of the evaluation device.

[0202] The fabrication of the above-mentioned device involves the following functional layer material structure:

[0203]

[0204]

[0205] The main luminescent material used as the control test device is a traditional main luminescent material, with MADN and BH001 being the control main luminescent materials.

[0206] The test data of the test devices made using the compounds of this invention and the test data of the control devices are shown in Table 3 below:

[0207] Table 3

[0208]

[0209]

[0210] As shown in Table 3, the device test data shows that, compared with traditional main light-emitting materials, the test device prepared using the preferred compound of this invention as the main light-emitting material has a lower driving voltage, significantly improved luminous brightness, and effectively improved overall device efficiency. Moreover, the device lifespan is consistent with, or even better than, that of traditional material devices. This demonstrates that using the preferred compound of this invention as the main light-emitting material plays a substantial role in improving device performance and has potential value for its promotion and application.

[0211] This invention adjusts the twisted posture of a twisted carbon molecule by introducing a planar structure into the twisted molecule, thereby achieving microscopic modification of the molecule, enhancing its conjugation, increasing its rigidity, and reducing its symmetry. This, in turn, raises the LOMO energy level and lowers the HOMO energy level, thus giving the molecule a larger energy system.

[0212] The electroluminescent device made of the large conjugated twisted molecules of this invention has a lower driving voltage, significantly improved luminous brightness, and effectively enhanced overall device efficiency. Moreover, the device lifespan is better than that of traditional material devices.

[0213] The large conjugated twisted molecule of this invention, as the main light-emitting material of electroluminescent devices, exhibits superior applicability and performance compared to traditional main light-emitting materials.

[0214] 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.

[0215] 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 large conjugated twisted molecule, characterized in that, The structural formulas of the twisted molecules include formula 1, formula 2, and formula 3: Where Z1 to Z8 represent C or CH, and R1 and R2 are selected from H, C1 to C, respectively. 15 One of alkyl, phenyl, and biphenyl; X is selected from O or S; Y is selected from CH2, O, or S.

2. The large conjugated twisted molecule according to claim 1, characterized in that, General formula 1 includes: The general formula 2 includes: Formula 3 includes: R1 and R2 are selected from H and C1 to C, respectively. 15 It is one of alkyl, phenyl, or biphenyl, where X is selected from O or S; and Y is selected from CH2, O, or S.

3. A large conjugated twisted molecule according to claim 2, characterized in that, The twisted molecules include compounds 1 to 169, with the following specific structural formulas:

4. An electroluminescent device, the 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 169 as described in claim 3.

5. An electroluminescent device according to claim 4, 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 the cathode and the anode, 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 main light-emitting material of the light-emitting layer is selected from, but is not limited to, any one or a combination of at least two of compounds 1 to 169.

6. An electroluminescent device according to claim 5, 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, and 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, and any combination thereof.

7. An electroluminescent device according to claim 5, characterized in that: 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 any one or a combination of at least two of compounds 1 to 169, and the weight ratio of the host light-emitting material to the guest light-emitting material is 90:10 to 95:

5.

8. An electroluminescent device according to claim 7, characterized in that: The guest luminescent material is selected from Ir(PPy)3 or DB-1, and its structural formula is as follows:

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