A compound for an organic electroluminescence device and an organic electroluminescence device comprising the same

Abstract

The present application provides a kind of compound for organic electroluminescence device and organic electroluminescence device comprising it.The structural general formula of the compound is as shown in formula I, wherein, Ar 1 , Ar 2 At least one of them has the structure shown in formula II.In the structure of formula II, it has a unique double X five-membered ring structure, and the unique five-membered ring structure has good thermal stability and electron-withdrawing ability, which not only improves the sublimation yield of the material, but also improves the hole injection ability of the hole injection layer in the preparation of organic electroluminescence device, reduces the voltage of the device, and improves the efficiency and service life of the device.

Description

Technical Field

[0001] This invention belongs to the field of OLED technology, specifically including a compound for organic electroluminescent devices and an organic electroluminescent device containing the same. Background Technology

[0002] Organic electronic devices include, but are not limited to, the following types: organic light-emitting diodes (OLEDs), organic field-effect transistors (O-FETs), organic light-emitting transistors (OLETs), organic photovoltaic devices (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photosensors, organic field-effect devices (OFQDs), light-emitting electrochemical cells (LECs), organic laser diodes, and organic electroluminescent devices.

[0003] In 1987, Tang and Van Slyke of Eastman Kodak reported a bilayer organic electroluminescent device comprising an arylamine hole transport layer and a tri-8-hydroxyquinoline-aluminum layer as both an electron transport and luminescent layer (Applied Physics Letters, 1987, 51(12): 913-915). Once a bias voltage was applied to the device, green light was emitted. This invention laid the foundation for the development of modern organic light-emitting diodes (OLEDs). State-of-the-art OLEDs can include multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more luminescent layers between the cathode and anode. Because OLEDs are self-emissive solid-state devices, they offer enormous potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well-suited for specialized applications, such as in the fabrication of flexible substrates.

[0004] OLEDs can be categorized into three different types based on their light-emitting mechanism. The OLED invented by Tang and van Slyke is a fluorescent OLED, which uses only singlet state emission. The triplet states generated in the device are wasted through non-radiative decay channels, resulting in an internal quantum efficiency (IQE) of only 25%, a limitation that hindered the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complexed heavy metals as the emitter. Therefore, both singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributed to the commercialization of active-matrix OLEDs (AMOLEDs). Recently, Adachi achieved high efficiency through thermally activated delayed fluorescence (TADF) of organic compounds. These emitters have small singlet-triple state gaps, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons can generate singlet excitons through reverse intersystem crossing, leading to high IQE.

[0005] OLEDs can also be classified into small-molecule OLEDs and polymer OLEDs based on the form of the materials used. Small molecules refer to any organic or organometallic material that is not a polymer. Small molecules can have large molecular weights, provided they have a precise structure. Dendritic polymers with well-defined structures are considered small molecules. Polymer OLEDs include conjugated polymers and non-conjugated polymers with side-chain luminescent groups. Small-molecule OLEDs can become polymer OLEDs if post-polymerization occurs during manufacturing.

[0006] Various OLED manufacturing methods exist. Small molecule OLEDs are typically manufactured via vacuum thermal evaporation. Polymer OLEDs are manufactured using solution methods, such as spin coating, inkjet printing, and nozzle printing. Small molecule OLEDs can also be manufactured using solution methods if the material can be dissolved or dispersed in a solvent.

[0007] The emission color of OLEDs can be achieved through the design of the luminescent material structure. OLEDs can include one or more luminescent layers to achieve the desired spectrum. Green, yellow, and red OLEDs using phosphorescent materials have been successfully commercialized. Blue phosphorescent devices still suffer from issues such as blue unsaturation, short device lifetime, and high operating voltage. Commercial full-color OLED displays typically employ a hybrid strategy, using blue fluorescence and phosphorescent yellow, or red and green. Currently, the rapid decrease in efficiency of phosphorescent OLEDs at high brightness remains a problem. Furthermore, a more saturated emission spectrum, higher efficiency, and longer device lifetime are desired.

[0008] p-type doped materials (PD materials) are a crucial class of materials in OLED devices, primarily used in conjunction with hole transport materials to form hole injection layers or p-type charge generation layers. In the fabrication of OLED display panels using PD materials, a typical process involves co-evaporation and thermal sublimation of the PD and hole transport materials to deposit a thin film on the substrate surface, followed by the gradual deposition of other functional layers and the light-emitting layer. Therefore, excellent PD materials require good thermal stability to withstand the prolonged high-temperature environment of the evaporation process, ensuring the performance of the deposited device. Good device performance also necessitates an excellent hole injection layer, requiring the PD material to have a low LUMO energy level to match well with the HOMO energy level of the hole transport material, thereby improving hole injection performance. This further necessitates the inclusion of various electron-withdrawing groups in the PD material. Therefore, researching PD materials with different substituents and finding PD materials that simultaneously possess excellent thermal stability and excellent doping ability is a key focus in the development of this type of material. Summary of the Invention

[0009] This invention aims to provide a series of organic compounds with dehydrogenated fused ring structures and special substituent groups to solve at least some of the aforementioned problems. These organic compounds can be used as charge transport materials, charge injection materials, and similar materials in organic electroluminescent devices. Due to their unique structural design, these novel organic compounds possess excellent hole injection capabilities and high thermal stability. These novel organic compounds can provide excellent performance for organic electroluminescent devices, such as reducing device voltage, improving device efficiency, and increasing lifetime.

[0010] Therefore, a first aspect of the present invention provides a compound for use in organic electroluminescent devices, the compound having the general structural formula shown in Formula I:

[0011]

[0012] In formula I,

[0013] W is selected from O, S, or Se each time it appears, either the same or different.

[0014] Ar 1 Ar 2 They may be the same or different, each independently selected from the group consisting of: hydrogen, deuterium, halogen, carbonyl, cyano, sulfinyl, sulfonyl, phosphoxy, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted aryloxy with 6-30 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl with 3-30 carbon atoms; and Ar 1 Ar2 At least one of them has the structure shown in Equation II.

[0015]

[0016] In formula II,

[0017] X is selected from O, S, and Se each time it appears, either identically or differently. Any one or any combination of them;

[0018] L, each time appearing, is selected from single bond, O, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, and combinations thereof;

[0019] R 3 The substituents representing ring A, each time appearing, may represent monosubstituted, polysubstituted, or unsubstituted groups, either the same or different.

[0020] Ring A is selected from any one of substituted or unsubstituted aromatic rings having 6-30 carbon atoms, or substituted or unsubstituted heteroaromatic rings having 3-30 carbon atoms;

[0021] R 1 R 2 R 3 Each group is independently selected from the following groups: hydrogen, deuterium, hydroxyl, mercapto, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphooxy, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted... The following are any one or any combination of aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, and substituted or unsubstituted amino groups having 0-20 carbon atoms.

[0022] R' and R” are each independently selected from the group consisting of: hydroxyl, mercapto, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, sulfinyl, sulfonyl, phosphooxy, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, and substituted or unsubstituted heterocyclic with 3-20 ring atoms. The group consists of any one or any combination of several of the following: alkyl, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aroxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, and substituted or unsubstituted heteroaryl having 3-30 carbon atoms.

[0023] And Ar 1 Ar 2 At least one of R' and R" is a group having at least one electron-withdrawing group; the Ar 1 Ar 2 ,R',R”R 1 R 2 R 3 In L, any adjacent substituents can bond with each other to form a ring;

[0024] * indicates the connection position of L with formula I, and * indicates the connection position of X with other groups.

[0025] Furthermore, the compound has the structure shown in Formula I-1:

[0026]

[0027] in,

[0028] In Equation I-1,

[0029] W is selected from O, S, or Se each time it appears, either the same or different.

[0030] X is selected from O, S, and Se each time it appears, either identically or differently. Any one or any combination of them;

[0031] L, each time appearing, is selected from single bond, O, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, and combinations thereof;

[0032] R 3The substituents representing ring A, each time appearing, may represent monosubstituted, polysubstituted, or unsubstituted groups, either the same or different.

[0033] Ring A is selected from any one of substituted or unsubstituted aromatic rings having 6-30 carbon atoms, or substituted or unsubstituted heteroaromatic rings having 3-30 carbon atoms;

[0034] Ar 1 The group consists of any one or any combination of the following: hydrogen, deuterium, halogen, carbonyl, cyano, sulfinyl, sulfonyl, phosphoxy, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 cyclic carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aryloxy having 6-30 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, and substituted or unsubstituted heteroaryl having 3-30 carbon atoms.

[0035] R 1 R 2 R 3 Each group is independently selected from the following groups: hydrogen, deuterium, hydroxyl, mercapto, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphooxy, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted... The following are any one or any combination of aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, and substituted or unsubstituted amino groups having 0-20 carbon atoms.

[0036] R' and R” are each independently selected from the group consisting of: hydroxyl, mercapto, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, sulfinyl, sulfonyl, phosphooxy, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, and substituted or unsubstituted heterocyclic with 3-20 ring atoms. The group consists of any one or any combination of several of the following: alkyl, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aroxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, and substituted or unsubstituted heteroaryl having 3-30 carbon atoms.

[0037] The R', R", R 1 R 2 R 3 In L, any adjacent substituents can bond with each other to form a ring.

[0038] Furthermore, the Ar 1 Ar 2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0039] Furthermore, when Ar 1 Ar 2 When substituents are present, the Ar 1 Ar 2 The substituents contained therein include at least one electron-withdrawing group.

[0040] Furthermore, the compound has the structure shown in Formula I-2:

[0041]

[0042] in,

[0043] In Equation I-2,

[0044] W is selected from O, S, or Se each time it appears, either the same or different.

[0045] X is selected from O, S, and Se each time it appears, either identically or differently. Any one or any combination of them;

[0046] L, each time appearing, is selected from single bond, O, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, and combinations thereof;

[0047] R 3 The substituents representing ring A, each time appearing, may represent monosubstituted, polysubstituted, or unsubstituted groups, either the same or different.

[0048] Ring A is selected from any one of substituted or unsubstituted aromatic rings having 6-30 carbon atoms, or substituted or unsubstituted heteroaromatic rings having 3-30 carbon atoms;

[0049] R 1 R 2 R 3 Each group is independently selected from the following groups: hydrogen, deuterium, hydroxyl, mercapto, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphooxy, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted... The following are any one or any combination of aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, and substituted or unsubstituted amino groups having 0-20 carbon atoms.

[0050] R' and R” are each independently selected from the group consisting of: hydroxyl, mercapto, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, sulfinyl, sulfonyl, phosphooxy, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, and substituted or unsubstituted heterocyclic with 3-20 ring atoms. The group consists of any one or any combination of several of the following: alkyl, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aroxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, and substituted or unsubstituted heteroaryl having 3-30 carbon atoms.

[0051] The R 1 R 2 R 3 In L, any adjacent substituents can bond with each other to form a ring.

[0052] Furthermore, the structure shown in Equation II is selected from one of the structures shown in Equations II-1 to II-6:

[0053]

[0054]

[0055] Z is selected from CR each time it appears, either the same or different. 3 Or N;

[0056] X is selected from O, S, and Se each time it appears, either identically or differently. Any one or any combination of them;

[0057] L, each time appearing, is selected from single bond, O, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, and combinations thereof;

[0058] R 1 R 2 R 3Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, hydroxyl, mercapto, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phospho, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, etc. The following are substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof.

[0059] The R 1 R 2 R 3 In this process, any adjacent substituents can bond with each other to form a ring;

[0060] * indicates the connection position of L with formula I, and * indicates the connection position of X with other groups.

[0061] Furthermore, the structure shown in Formula II is selected from the structure shown in Formula II-1 or Formula II-2.

[0062] Furthermore, R 1 R 2Each time it appears, it is selected from the group consisting of the following, either identically or differently: hydrogen, deuterium, halogen, nitrosyl, nitro, carbonyl, cyano, SF5, sulfinyl, sulfonyl, phosphoxy, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocyclic groups having 3-20 ring atoms, substituted or unsubstituted groups having Any one or any combination of aralkyl groups with 7-30 carbon atoms, substituted or unsubstituted alkoxy groups with 1-20 carbon atoms, substituted or unsubstituted aroxy groups with 6-30 carbon atoms, substituted or unsubstituted alkenyl groups with 2-20 carbon atoms, substituted or unsubstituted alkynyl groups with 2-20 carbon atoms, substituted or unsubstituted aryl groups with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3-30 carbon atoms.

[0063] The R 1 R 2 In this process, any adjacent substituents can bond with each other to form a ring.

[0064] Furthermore, the W is selected from O; and / or

[0065] The R' and R" are selected, in the same or different manner each time they appear, from the group consisting of: fluorine, cyano, SCN, sulfonyl, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted aroxy with 6-30 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl with 3-30 carbon atoms; and / or

[0066] R 1 R 2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, carbonyl, cyano, SF5, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0067] Furthermore, when R 1 R 2When R is selected, in each instance, either identically or differently, from substituted alkyl groups having 1-20 carbon atoms, substituted aralkyl groups having 7-30 carbon atoms, substituted alkoxy groups having 1-20 carbon atoms, substituted aroxy groups having 6-30 carbon atoms, substituted aryl groups having 6-30 carbon atoms, or substituted heteroaryl groups having 3-30 carbon atoms, it is considered that R 1 R 2 The substituents contained therein include at least one electron-withdrawing group.

[0068] Further, the electron-withdrawing group is selected from the group consisting of: halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphoxy, azirrocycloyl, and any of the following groups substituted by one or more of halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphoxy, azirrocycloyl, having 1-20 Alkyl groups having carbon atoms, cycloalkyl groups having 3-20 carbon atoms, heteroalkyl groups having 1-20 carbon atoms, aralkyl groups having 7-30 carbon atoms, alkoxy groups having 1-20 carbon atoms, aryloxy groups having 6-30 carbon atoms, alkenyl groups having 2-20 carbon atoms, alkynyl groups having 2-20 carbon atoms, aryl groups having 6-30 carbon atoms, heteroaryl groups having 3-30 carbon atoms, alksilyl groups having 3-20 carbon atoms, arylsilyl groups having 6-20 carbon atoms, and combinations thereof.

[0069] Further, the electron-withdrawing group is selected from the group consisting of: fluorine, cyano, isocyano, SCN, OCN, SF5 and any of the following groups substituted by one or more of fluorine, cyano, isocyano, SCN, OCN, SF5: alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 cyclic carbon atoms, heteroalkyl having 1-20 carbon atoms, aralkyl having 7-30 carbon atoms, alkoxy having 1-20 carbon atoms, aroxy having 6-30 carbon atoms, aryl having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, alkoxyl having 3-20 carbon atoms, arylsilyl having 6-20 carbon atoms, and combinations thereof.

[0070] Furthermore, the electron-withdrawing group is selected from the group consisting of: F, CF3, OCF3, SF5, SO2CF3, cyano, isocyano, SCN, OCN, pyrimidinyl, triazine, and combinations thereof.

[0071] Furthermore, X is selected from O, S, or [other criteria] each time it appears.

[0072] Furthermore, X is selected from O; and / or

[0073] At least one of R' and R" is selected from cyano.

[0074] Furthermore, L, each time it appears, is selected from single bonds, O, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

[0075] Ring A is a substituted or unsubstituted aromatic ring with 6-30 carbon atoms, or a substituted or unsubstituted heteroaromatic ring with 3-30 carbon atoms.

[0076] Furthermore, when ring A has substituents, ring A can be represented by one or more R groups each time it appears. 3 Instead, L can be replaced by a single or multiple R each time it appears. 4 replace;

[0077] The R 3 R 4 Each occurrence may be selected, either identically or differently, from the group consisting of: hydrogen, deuterium, hydroxyl, mercapto, halogen, carbonyl, cyano, SF5, sulfonyl, phosphoxy, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms; any combination of one or more of the following: adjacent R 3 R 4 They can be arbitrarily connected to form a ring.

[0078] Furthermore, L, each time appearing, is selected from the same or different groups: single bond, O, substituted or unsubstituted phenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted naphthinylene, substituted or unsubstituted phenanthrolinel, substituted or unsubstituted anthracene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazolyl, and combinations thereof.

[0079] Furthermore, each occurrence of L can be represented by a single or multiple R. 4 Replace, R 4Each occurrence may be selected, either identically or differently, from the group consisting of: hydrogen, deuterium, hydroxyl, mercapto, halogen, carbonyl, cyano, SF5, sulfonyl, phosphoxy, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms; any combination of one or more of the following: adjacent R 4 They can be arbitrarily connected to form a loop;

[0080] Furthermore, L, each time it appears, is selected from single bonds, O, and the following structures, and combinations thereof:

[0081]

[0082]

[0083]

[0084] In the above-mentioned compounds, hydrogen may be partially or completely replaced by deuterium;

[0085] “ “” indicates the connection position of L with formula I or other L, “…” indicates the connection position of L with ring A or other L.

[0086] Furthermore, Ar 1 Ar 2 ,R',R”R 1 R 2 R 3 R 4 Each occurrence is either identical or different from the group consisting of the following structures:

[0087]

[0088]

[0089]

[0090]

[0091] In the above-mentioned compounds, hydrogen may be partially or completely replaced by deuterium;

[0092] “ "" indicates the connection point between the above structure and other structures.

[0093] Further, the compound is selected from the group consisting of compounds P1-1 to P1-1028, compounds P2-1 to P2-1028, compounds P3-1 to P3-1028, and compounds P4-1 to P4-1028.

[0094] The compounds P1-1 to P1-1028 have structures represented by formula I-1-1; wherein R 1 R 2 Similarly, the W and Ar mentioned above 1 R 1 R 2 X and L correspond to atoms or groups selected from those shown in Table 1 below:

[0095]

[0096] Table 1

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107] The compounds P2-1 to P2-1028 have structures represented by formula I-1-2; wherein R 1 R 2 Similarly, the W and Ar mentioned above 1 R 1 R 2 X and L correspond to atoms or groups selected from those shown in Table 2 below:

[0108]

[0109] Table 2

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121] The compounds P3-1 to P3-1028 have structures represented by formula I-2-1; wherein R 1 R 2 The same applies to W, Z, and R. 1 R 2 X and L correspond to atoms or groups selected from those shown in Table 3 below:

[0122]

[0123] Table 3

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134] The compounds P4-1 to P4-1028 have structures represented by formula I-2-2; wherein R 1 R 2 The same applies to W, Z, and R. 1 R 2 X and L correspond to atoms or groups selected from those shown in Table 4 below:

[0135]

[0136] Table 4

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148] In the above-mentioned compounds, hydrogen may be partially or completely replaced by deuterium.

[0149] Secondly, an organic electroluminescent device is provided, the organic electroluminescent device comprising:

[0150] anode,

[0151] cathode,

[0152] And an organic layer disposed between the anode and the cathode, wherein the organic layer contains the compound described above.

[0153] Furthermore, the organic layer is a hole injection layer or a hole transport layer, and the hole injection layer or hole transport layer is formed solely from the compound described above.

[0154] Further, the organic layer is a hole injection layer or a hole transport layer, and the hole injection layer or hole transport layer further comprises at least one hole transport material; the mass doping ratio of the compound to the at least one hole transport material is from 1000:1 to 1:1000; preferably, the mass doping ratio of the compound to the at least one hole transport material is from 10:1 to 1:100.

[0155] Furthermore, the organic electroluminescent device includes at least two light-emitting units, and the organic layer is a charge-generating layer disposed between the at least two light-emitting units, wherein the charge-generating layer includes a p-type charge-generating layer and an n-type charge-generating layer;

[0156] The p-type charge generation layer contains the compounds described above;

[0157] The p-type charge generation layer further comprises at least one hole transport material, wherein the mass doping ratio of the compound to the at least one hole transport material is 1000:1 to 1:1000; preferably, the mass doping ratio of the compound to the at least one hole transport material is 10:1 to 1:100.

[0158] Furthermore, the hole transport material is selected from compounds having triarylamine units, spirodifluorene compounds, pentanebenzene compounds, oligothiophene compounds, oligophenyl compounds, oligophenylene vinylidene compounds, oligofluorene compounds, porphyrin complexes, or metal phthalocyanine complexes.

[0159] Furthermore, the charge generation layer also includes a buffer layer disposed between the p-type charge generation layer and the n-type charge generation layer, the buffer layer comprising the compound described above.

[0160] Thirdly, a display component is provided, the display component comprising the organic electroluminescent device as described above.

[0161] The beneficial effects of this invention are as follows:

[0162] This invention provides an organic compound and an organic electroluminescent device comprising the same. The organic compound has the structure shown in Formula I. This organic compound is a compound with a multi-substituted dehydrogenated fused ring structure containing multiple substituted groups, wherein at least one of Ar1 and Ar2 has the structure shown in Formula II. Formula II has a unique double-X five-membered ring structure, which possesses both excellent thermal stability and stable electron-withdrawing ability. Connecting this unique double-X five-membered ring structure to the multi-substituted dehydrogenated fused ring core not only improves the material's sublimation yield but also provides excellent doping capability. When used to fabricate organic electroluminescent devices, it can improve the hole injection capability of the hole injection layer, reduce the device voltage, and improve device efficiency and lifetime. Furthermore, in Formula II of the compound provided by this invention, the double-X five-membered ring structure is connected to the multi-substituted dehydrogenated fused ring core through a spacer group L, which can significantly improve the material's sublimation yield. Attached Figure Description

[0163] Figure 1 This is a schematic diagram of an organic electroluminescent device according to an embodiment of the present invention, wherein the device 100 includes a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190.

[0164] Figure 2 This is a schematic diagram of an organic light-emitting device with an encapsulation layer according to an embodiment of the present invention, wherein the device 200 includes a substrate 201, an anode 210, a hole injection layer 220, a hole transport layer 230, an electron blocking layer 240, a light-emitting layer 250, a hole blocking layer 260, an electron transport layer 270, an electron injection layer 280, a cathode 290, and an encapsulation layer 202.

[0165] Figure 3 This is a schematic diagram of a series organic light-emitting device with an encapsulation layer according to an embodiment of the present invention. The device 300 includes a substrate 301, an anode 310, a first hole injection layer 311, a first hole transport layer 312, a first electron blocking layer 313, a first light-emitting layer 314, a first hole blocking layer 315, a first electron transport layer 316, an N-type charge generation layer 320, a P-type charge generation layer 321, a second hole injection layer 330, a second hole transport layer 331, a second electron blocking layer 332, a second light-emitting layer 333, a second hole blocking layer 334, a second electron transport layer 335, a second electron injection layer 336, a cathode 337, and an encapsulation layer 302. Detailed Implementation

[0166] To more clearly illustrate the present invention, the following description, in conjunction with preferred embodiments and accompanying drawings, further clarifies the invention. Those skilled in the art should understand that the specific description below is illustrative rather than restrictive and should not be construed as limiting the scope of protection of the present invention. The embodiments and comparative examples in this specification are provided to provide a more complete explanation of the specification to those skilled in the art. Various modifications can be made based on the embodiments and comparative examples in this specification, and the scope of protection of the present invention should not be limited to the embodiments and comparative examples detailed below.

[0167] The organic compounds of this invention are applicable to light-emitting elements, display panels, and electronic devices, particularly organic electroluminescent devices. The electronic devices of this invention are devices comprising a layer of at least one organic compound, and may also comprise layers of inorganic materials or layers formed entirely of inorganic materials. Preferred electronic devices include organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic dye-sensitized solar cells (O-DSSCs), organic optical detectors, organic photosensors, organic field quenching devices (O-FQDs), light-emitting electrochemical cells (LECs), organic laser diodes (O-lasers), and organic plasma emitting devices. Organic electroluminescent devices (OLEDs) are particularly preferred, and their device structures, for example, have the following characteristics: Figure 1 , Figure 2 or Figure 3 The structure shown.

[0168] Definition of the term "substituent group"

[0169] Halogens or halides—as used herein—include fluorine, chlorine, bromine, and iodine.

[0170] Alkyl – as used herein, includes straight-chain and branched alkyl groups. An alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred.

[0171] Cycloalkyl – as used herein, includes cyclic alkyl groups. A cycloalkyl group can be a cycloalkyl group having 3 to 20 carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, and 4,4-dimethylcyclohexyl are preferred.

[0172] Heteroalkyl – as used herein, a heteroalkyl group comprises one or more carbon atoms in an alkyl chain that are replaced by heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. The heteroalkyl group can be a heteroalkyl group having 1 to 20 carbon atoms, preferably a heteroalkyl group having 1 to 10 carbon atoms, and more preferably a heteroalkyl group having 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminopropyl, dimethylaminomethyl, trimethylgermanylmethyl, trimethylgermanylethyl, trimethylgermanylisopropyl, dimethylethylgermanylmethyl, dimethylisopropylgermanylmethyl, tert-butyldimethylgermanylmethyl, triethylgermanylmethyl, triethylgermanylethyl, triisopropylgermanylmethyl, triisopropylgermanylethyl, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisopropyl, triisopropylsilylmethyl, triisopropylsilylethyl.

[0173] Alkenyl – as used herein, encompasses straight-chain, branched, and cyclic olefinic groups. An alkenyl group can be an alkenyl group containing 2 to 20 carbon atoms, preferably an alkenyl group having 2 to 10 carbon atoms. Examples of alkenyl groups include vinyl, propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-methylvinyl, styryl, 2,2-diphenylvinyl, 1,2-diphenylvinyl, 1-methylallyl, 1,1-dimethylallyl, 2-methylallyl, 1-phenylallyl, 2-phenylallyl, 3-phenylallyl, 3,3-diphenylallyl, 1,2-dimethylallyl, 1-phenyl-1-butenyl, 3-phenyl-1-butenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cycloheptenyl, cyclohepttrienyl, cyclooctenyl, cyclooctatetraenyl, and norbornyl.

[0174] Alkynyl – as used herein, encompasses straight-chain alkynyl groups. An alkynyl group can be one containing 2 to 20 carbon atoms, preferably one having 2 to 10 carbon atoms. Examples of alkynyl groups include ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3,3-dimethyl-1-butynyl, 3-ethyl-3-methyl-1-pentynyl, 3,3-diisopropyl-1-pentynyl, phenylethynyl, phenylpropynyl, etc. Among the above, ethynyl, propynyl, propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, and phenylethynyl are preferred. Furthermore, the alkynyl group may optionally be substituted.

[0175] Aryl or aromatic group – as used herein, both non-fused and fused systems are considered. The aryl group can be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, perylene, and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene, and naphthalene. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4”-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene, and m-tetraphenyl. Additionally, the aryl group may optionally be substituted.

[0176] Aromatic or aryl-aryl – as used herein – refers to a divalent group formed by the further loss of a hydrogen atom from an aryl group.

[0177] Aromatic ring – as used herein – can refer to an aromatic cyclic group, which can be non-fused or fused aromatic cyclic groups.

[0178] Heterocyclic groups or heterocycles – as used herein, consider non-aromatic cyclic groups. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-20 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-20 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron atoms. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacyclic, dioxahexacyclic, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolidinyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiorroleyl. In addition, the heterocyclic group can be optionally substituted.

[0179] Heteroaryl – as used herein – can be a non-fused or fused heteroaryl group comprising 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. Heteroaryl can be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolecarbazole, pyridineindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxthiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquinoline Phosphine, cyclophosphine, quinazoline, quinoxaline, naphthidine, phthalazine, pteridine, xanthan, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0180] A heteroaryl or heteroaryl group—as used herein—refers to a divalent group formed by the further loss of a hydrogen atom from a heteroaryl group.

[0181] Heteroaromatic ring – as used herein, can refer to a heteroaromatic cyclic group, which can be unfused or fused heteroaromatic cyclic groups. Alkoxy – as used herein, is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. Alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, alkoxy groups may optionally be substituted.

[0182] Aryloxy group – as used herein, is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. The aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy groups. Additionally, the aryloxy group may optionally be substituted.

[0183] Arylalkyl – as used herein, encompasses aryl-substituted alkyl groups. An arylalkyl group can be an arylalkyl group having 7 to 30 carbon atoms, preferably an arylalkyl group having 7 to 20 carbon atoms, and more preferably an arylalkyl group having 7 to 13 carbon atoms. Examples of arylalkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthyl-ethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl The compounds include alkyl groups, such as o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0184] Alkylsilyl – as used herein, encompasses alkyl-substituted silyl groups. The alkylsilyl group can be an alkylsilyl group having 3 to 20 carbon atoms, preferably an alkylsilyl group having 3 to 10 carbon atoms. Examples of alkylsilyl groups include trimethylsilyl, triethylsilyl, methyldiethylsilyl, ethyldimethylsilyl, tripropylsilyl, tributylsilyl, triisopropylsilyl, methyldiisopropylsilyl, dimethylisopropylsilyl, tritert-butylsilyl, triisobutylsilyl, dimethyltert-butylsilyl, and methylditert-butylsilyl. Furthermore, the alkylsilyl group may optionally be substituted.

[0185] Arylsilane – as used herein, encompasses at least one aryl-substituted silane group. The arylsilane can be an arylsilane having 6 to 30 carbon atoms, preferably an arylsilane having 8 to 20 carbon atoms. Examples of arylsilanes include triphenylsilyl, phenyldiphenylsilyl, diphenylbiphenylsilyl, phenyldiethylsilyl, diphenylethylsilyl, phenyldimethylsilyl, diphenylmethylsilyl, phenyldiisopropylsilyl, diphenylisopropylsilyl, diphenylbutylsilyl, diphenylisobutylsilyl, and diphenyltert-butylsilyl. Additionally, the arylsilane may optionally be substituted.

[0186] Alkylgermanium group – as used herein, encompasses alkyl-substituted germanium groups. The alkylgermanium group can be an alkylgermanium group having 3 to 20 carbon atoms, preferably an alkylgermanium group having 3 to 10 carbon atoms. Examples of alkylgermanium groups include trimethylgermanium, triethylgermanium, methyldiethylgermanium, ethyldimethylgermanium, tripropylgermanium, tributylgermanium, triisopropylgermanium, methyldiisopropylgermanium, dimethylisopropylgermanium, tritert-butylgermanium, triisobutylgermanium, dimethyltert-butylgermanium, and methylditert-butylgermanium. Furthermore, the alkylgermanium group may optionally be substituted.

[0187] Arylgermanium – as used herein, encompasses a germanium group substituted with at least one aryl or heteroaryl group. The arylgermanium group can be an arylgermanium group having 6 to 30 carbon atoms, preferably an arylgermanium group having 8 to 20 carbon atoms. Examples of arylgermanium groups include triphenylgermanium, phenyldiphenylgermanium, diphenylbiphenylgermanium, phenyldiethylgermanium, diphenylethylgermanium, phenyldimethylgermanium, diphenylmethylgermanium, phenyldiisopropylgermanium, diphenylisopropylgermanium, diphenylbutylgermanium, diphenylisobutylgermanium, and diphenyltert-butylgermanium. Additionally, the arylgermanium group may optionally be substituted.

[0188] The term "aza" in azadibenzofuran, azadibenzothiophene, etc., refers to the substitution of one or more CH groups in the corresponding aromatic segment by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoxaline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.

[0189] In this disclosure, unless otherwise defined, when using any term from the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclic, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted alkylgermanium, substituted arylgermanium, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, etc. The substituted sulfinyl group, substituted sulfonyl group, substituted phosphoxy group refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, heterocyclic, aralkyl, alkoxy, aryl, alkenyl, alkynyl, aryl, heteroaryl, alkylsilyl, arylsilyl, alkylgermanium, arylgermanium, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphoxy group. One or more groups can be selected from deuterium, halogen, unsubstituted alkyl with 1-20 carbon atoms, and unsubstituted cycloalkyl with 3-20 cyclic carbon atoms. Alkyl groups, unsubstituted heteroalkyl groups having 1-20 carbon atoms, unsubstituted heterocyclic groups having 3-20 ring atoms, unsubstituted aralkyl groups having 7-30 carbon atoms, unsubstituted alkoxy groups having 1-20 carbon atoms, unsubstituted aryloxy groups having 6-30 carbon atoms, unsubstituted alkenyl groups having 2-20 carbon atoms, unsubstituted alkynyl groups having 2-20 carbon atoms, unsubstituted aryl groups having 6-30 carbon atoms, and unsubstituted heteroaryl groups having 3-30 carbon atoms. The group includes unsubstituted alkylsilyl groups having 3-20 carbon atoms, unsubstituted arylsilyl groups having 6-20 carbon atoms, unsubstituted alkylgermanium groups having 3-20 carbon atoms, unsubstituted arylgermanium groups having 6-20 carbon atoms, and unsubstituted amino, hydroxyl, mercapto, O, S, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, nitro, nitroso, sulfinyl, sulfonyl, phosphoxy, and combinations thereof having 0-20 carbon atoms.

[0190] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or attaching segments are considered equivalent.

[0191] In the compounds mentioned in this disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon, nitrogen, oxygen, phosphorus, and boron can also be replaced by their other stable isotopes. Substitution with other stable isotopes in the compounds is likely preferred due to its ability to enhance device efficiency and stability.

[0192] In the compounds mentioned in this disclosure, multiple substitution refers to a range including disubstituted substitutions, up to the maximum number of available substitutions. When a substituent in a compound mentioned in this disclosure represents multiple substitution (including disubstituted, trisubstituted, tetrasubstituted, etc.), it means that the substituent can be present at multiple available substitution positions in its linkage structure. The substituent present at multiple available substitution positions can have the same structure or different structures. In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally link to form a ring, adjacent substituents in the compound cannot link to form a ring. In the compounds mentioned in this disclosure, the optional linking of adjacent substituents to form a ring includes both cases where adjacent substituents can link to form a ring and cases where adjacent substituents do not link to form a ring. When adjacent substituents can optionally link to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged, fused rings, etc.), as well as an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this formulation, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0193] The statement that adjacent substituents can optionally connect to form a ring or bond to form a ring is also intended to be understood as referring to two substituents bonded to the same carbon atom connecting to each other by chemical bonds to form a ring, as exemplified by the following formula:

[0194]

[0195] The statement that adjacent substituents can optionally connect to form a ring or bond to form a ring is also intended to be understood as referring to two substituents bonded to carbon atoms directly bonded to each other forming a ring by chemical bonds, as exemplified by the following formula:

[0196]

[0197] The statement that adjacent substituents can optionally connect to form a ring or bond to form a ring is also intended to be understood as referring to two substituents bonded to a further distant carbon atom connecting to each other by chemical bonds to form a ring, which can be exemplified by the following formula:

[0198]

[0199] Furthermore, the statement that adjacent substituents can optionally connect to form a ring or bond to form a ring is also intended to mean that, in the case where one of the two adjacent substituents represents hydrogen, the second substituent bonds to the position where the hydrogen atom is bonded, thereby forming a ring. This is illustrated by the following example:

[0200]

[0201] The first and second compounds used in this invention can be obtained by referring to the preparation methods in the prior art, and will not be described in detail here.

[0202] The fabrication method of organic electroluminescent devices is not limited. The fabrication method in the following embodiments is merely an example and should not be construed as limiting. Those skilled in the art can reasonably improve the fabrication method of the following embodiments based on existing technology. For example, the proportions of various materials in each organic layer are not particularly limited, and those skilled in the art can reasonably select them within a certain range based on existing technology. In the device embodiments, the device characteristics are tested using conventional equipment in the art and methods well known to those skilled in the art. Since those skilled in the art are familiar with the above-mentioned equipment usage, testing methods, and other related content, and can obtain the inherent data of the sample definitively and unaffected, the above-mentioned related content will not be elaborated further in this patent.

[0203] Synthesis Examples

[0204] The preparation method of the compounds of this invention is not limited, and the raw materials used can be purchased or synthesized by oneself.

[0205] Among them, the structural unit segment in Equation II It can be synthesized through the following method:

[0206]

[0207] The obtained fragments can also be coupled with halogenated compounds to finally prepare the starting compound, which is used to synthesize the compound of this invention, as shown below:

[0208]

[0209] The above preparation methods are not limited and are for reference only. The atoms in the above structures can be replaced by other atoms or groups. The raw materials used can be purchased. For specific implementation methods, please refer to the methods disclosed in this field.

[0210] The preparation methods of the compounds of this invention are not limited. Typical but not limited examples are the following compounds, whose synthetic routes and preparation methods are as follows:

[0211] Synthesis Example 1: Synthesis of Compound P1-493

[0212] Step 1: Synthesis of intermediate P1-493-A

[0213]

[0214] In a 2L two-necked flask, intermediates SM0 (30.5g, 95.9mmol), P1-493-SM1 (30.2g, 116.9mmol), P1-493-SM2 (52.6g, 117.9mmol), potassium phosphate trihydrate (64.0g, 240.5mmol), Pd2(dba)3 (1.15g, 1.252mmol), and SPhos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 2.16g, 5.263mmol) were added sequentially. Nitrogen gas was purged three times. Under nitrogen protection, 1000mL of toluene and 250mL of water were added, and the mixture was heated to 100℃ and reacted overnight. After the reaction was complete, the mixture was cooled, extracted with an appropriate amount of tetrahydrofuran, dried with anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P1-493-A (8.14 g, yield 11%).

[0215] Step 2: Synthesis of intermediate P1-493-B

[0216]

[0217] In a 2L two-necked flask, intermediate P1-493-A (8.14 g, 10.54 mmol) was added. Under nitrogen protection, 800 mL of ultra-dry THF was added, and the mixture was cooled to -30 °C. Then, lithium bis(trimethylsilyl)amino (LiHMDS, 30 mL, 30 mmol) was added dropwise. The mixture was reacted at this temperature for 2 h. Then, elemental iodine (7.70 g, 30.3 mmol) was added, and the mixture was heated to room temperature for 0.5 h. The reaction was quenched with saturated sodium sulfite solution, extracted with an appropriate amount of ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P1-493-B (10.3 g, 95% yield).

[0218] Step 3: Synthesis of intermediate P1-493-C

[0219]

[0220] In a 2L two-necked flask, intermediate P1-493-B (10.3 g, 10.0 mmol), malononitrile (3.21 g, 48.6 mmol), potassium carbonate (10.8 g, 78.1 mmol), and Pd(PPh3)4 (0.462 g, 0.400 mmol) were added sequentially. Under nitrogen protection, 350 mL of DMF was added, and the mixture was heated to 80 °C and reacted overnight. After the reaction was complete, the mixture was cooled to room temperature and then cooled in an ice-water bath. The reaction solution was slowly added dropwise to 3N hydrochloric acid, resulting in the precipitation of a large amount of yellow solid. The crude product was filtered to obtain a white solid intermediate P1-493-C (7.20 g, 80% yield) by crystallization.

[0221] Step 4: Synthesis of compound P1-493

[0222]

[0223] Under a nitrogen atmosphere, intermediate P1-493-C (7.20 g, 8.00 mmol) was added to a 3 L single-necked flask, followed by 1000 mL of DCM. Bis(trifluoroacetoxy)iodobenzene (PIFA, 6.35 g, 14.76 mmol) was added in portions at room temperature. After stirring at room temperature for 2 days, the reaction mixture was concentrated to a suitable volume and filtered to obtain a black solid compound P1-493 (5.60 g, 78% yield). The product was identified as the target product with a molecular weight of 898.0.

[0224] Synthesis Example 2: Synthesis of Compound P2-257

[0225] Step 1: Synthesis of intermediate P2-257-A

[0226]

[0227] In a 2L two-necked flask, intermediates SM0 (30.8g, 96.9mmol), P2-257-SM1 (29.7g, 115.3mmol), P2-257-SM2 (35.8g, 118.6mmol), potassium phosphate trihydrate (62.0g, 232.8mmol), Pd2(dba)3 (1.15g, 1.252mmol), and SPhos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 2.16g, 5.263mmol) were added sequentially. Nitrogen gas was purged three times. Under nitrogen protection, 1000mL of toluene and 250mL of water were added, and the mixture was heated to 100℃ and reacted overnight. After the reaction was complete, the mixture was cooled, extracted with an appropriate amount of tetrahydrofuran, dried with anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P2-257-A (7.67 g, yield 15%).

[0228] Step 2: Synthesis of intermediate P2-257-B

[0229]

[0230] In a 2L two-necked flask, intermediate P2-257-A (7.67 g, 14.54 mmol) was added. Under nitrogen protection, 800 mL of ultradry THF was added, and the mixture was cooled to -30 °C. Then, lithium bis(trimethylsilyl)amino (LiHMDS, 45 mL, 45 mmol) was added dropwise. The mixture was reacted at this temperature for 2 h. Then, elemental iodine (12.8 g, 50.3 mmol) was added, and the mixture was heated to room temperature for 0.5 h. The reaction was quenched with saturated sodium sulfite solution, extracted with an appropriate amount of ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P2-257-B (10.5 g, 93% yield).

[0231] Step 3: Synthesis of intermediate P2-257-C

[0232]

[0233] In a 2L two-necked flask, intermediate P2-257-B (10.5 g, 13.5 mmol), malononitrile (3.60 g, 54.6 mmol), potassium carbonate (9.43 g, 68.2 mmol), and Pd(PPh3)4 (0.443 g, 0.382 mmol) were added sequentially. Under nitrogen protection, 350 mL of DMF was added, and the mixture was heated to 80 °C and reacted overnight. After the reaction was complete, the mixture was cooled to room temperature and then cooled in an ice-water bath. The reaction solution was slowly added dropwise to 3N hydrochloric acid, resulting in the precipitation of a large amount of yellow solid. The crude product was filtered to obtain a white solid intermediate P2-257-C (7.44 g, 84% yield) by crystallization.

[0234] Step 4: Synthesis of compound P2-257

[0235]

[0236] Under a nitrogen atmosphere, intermediate P2-257-C (7.44 g, 11.34 mmol) was added to a 3 L single-necked flask, followed by 1000 mL of DCM. Bis(trifluoroacetoxy)iodobenzene (PIFA, 7.40 g, 17.20 mmol) was added in portions at room temperature. After stirring at room temperature for 2 days, the reaction mixture was concentrated to a suitable volume and filtered to obtain a black solid compound P2-257 (6.38 g, 86% yield). The product was identified as the target product with a molecular weight of 654.0.

[0237] Synthesis Example 3: Synthesis of Compound P2-271

[0238] Step 1: Synthesis of intermediate P2-271-A

[0239]

[0240] In a 2L two-necked flask, intermediates SM0 (31.5g, 98.9mmol), P2-271-SM1 (22.6g, 118.5mmol), P2-271-SM2 (41.7g, 120.4mmol), potassium phosphate trihydrate (63.1g, 236.8mmol), Pd2(dba)3 (1.15g, 1.252mmol), and SPhos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 2.16g, 5.263mmol) were added sequentially. Nitrogen gas was purged three times. Under nitrogen protection, 1000mL of toluene and 250mL of water were added, and the mixture was heated to 100℃ and reacted overnight. After the reaction was complete, the mixture was cooled, extracted with an appropriate amount of tetrahydrofuran, dried with anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P2-271-A (8.38 g, yield 14%).

[0241] Step 2: Synthesis of intermediate P2-271-B

[0242]

[0243] In a 2L two-necked flask, intermediate P2-271-A (8.38 g, 13.8 mmol) was added. Under nitrogen protection, 800 mL of ultradry THF was added, and the temperature was lowered to -30°C. Then, lithium bis(trimethylsilyl)amino (LiHMDS, 45 mL, 45 mmol) was added dropwise. The reaction was carried out at this temperature for 2 h. Then, elemental iodine (12.3 g, 48.3 mmol) was added, and the reaction was raised to room temperature for 0.5 h. The reaction was quenched with saturated sodium sulfite solution, extracted with an appropriate amount of ethyl acetate, dried with anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain white solid intermediate P2-271-B (10.8 g, 91% yield).

[0244] Step 3: Synthesis of intermediate P2-271-C

[0245]

[0246] In a 2L two-necked flask, intermediate P2-271-B (10.8 g, 12.6 mmol), malononitrile (3.34 g, 50.6 mmol), potassium carbonate (8.07 g, 58.4 mmol), and Pd(PPh3)4 (0.210 g, 0.182 mmol) were added sequentially. Under nitrogen protection, 350 mL of DMF was added, and the mixture was heated to 80 °C and reacted overnight. After the reaction was complete, the mixture was cooled to room temperature and then cooled in an ice-water bath. The reaction solution was slowly added dropwise to 3N hydrochloric acid, resulting in the precipitation of a large amount of yellow solid. The crude product was filtered to obtain a white solid intermediate P2-271-C (7.67 g, 83% yield) by crystallization.

[0247] Step 4: Synthesis of compound P2-271

[0248]

[0249] Under a nitrogen atmosphere, intermediate P2-271-C (7.67 g, 10.46 mmol) was added to a 3 L single-necked flask, followed by 1000 mL of DCM. Bis(trifluoroacetoxy)iodobenzene (PIFA, 7.40 g, 17.20 mmol) was added in portions at room temperature. After stirring at room temperature for 2 days, the reaction mixture was concentrated to a suitable volume and filtered to obtain a black solid compound P2-271 (6.81 g, 89% yield). The product was identified as the target product with a molecular weight of 731.1.

[0250] Synthesis Example 4: Synthesis of Compound P3-115

[0251] Step 1: Synthesis of intermediate P3-115-A

[0252]

[0253] In a 2L two-necked flask, intermediates SM0 (10.6 g, 33.3 mmol), P3-115-SM1 (34.5 g, 116.5 mmol), potassium phosphate trihydrate (36.2 g, 136.2 mmol), Pd2(dba)3 (1.46 g, 1.59 mmol), and SPhos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 2.26 g, 5.50 mmol) were added sequentially. The mixture was purged with nitrogen three times. Under nitrogen protection, 800 mL of toluene and 200 mL of water were added, and the mixture was heated to 100 °C and reacted overnight. After the reaction was complete, the mixture was cooled, extracted with a suitable amount of tetrahydrofuran, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P3-115-A (18.0 g, 82% yield).

[0254] Step 2: Synthesis of intermediate P3-115-B

[0255]

[0256] In a 2L two-necked flask, intermediate P3-115-A (18.0 g, 27.3 mmol) was added. Under nitrogen protection, 800 mL of ultradry THF was added, and the mixture was cooled to -30 °C. Then, lithium bis(trimethylsilyl)amino (LiHMDS, 65 mL, 65 mmol) was added dropwise. The mixture was reacted at this temperature for 2 h. Then, elemental iodine (17.8 g, 70.2 mmol) was added, and the mixture was heated to room temperature for 0.5 h. The reaction was quenched with saturated sodium sulfite solution, extracted with an appropriate amount of ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P3-115-B (22.4 g, 90% yield).

[0257] Step 3: Synthesis of intermediate P3-115-C

[0258]

[0259] In a 2L two-necked flask, intermediate P3-115-B (22.4 g, 24.6 mmol), malononitrile (6.31 g, 95.6 mmol), potassium carbonate (13.6 g, 98.4 mmol), and Pd(PPh3)4 (0.340 g, 0.294 mmol) were added sequentially. Under nitrogen protection, 350 mL of DMF was added, and the mixture was heated to 80 °C and reacted overnight. After the reaction was complete, the mixture was cooled to room temperature and then cooled in an ice-water bath. The reaction solution was slowly added dropwise to 3N hydrochloric acid, resulting in the precipitation of a large amount of yellow solid. The crude product was filtered to obtain a white solid intermediate P3-115-C (15.7 g, 81% yield) by crystallization.

[0260] Step 4: Synthesis of compound P3-115

[0261]

[0262] Under a nitrogen atmosphere, intermediate P3-115-C (15.7 g, 19.9 mmol) was added to a 3 L single-necked flask, followed by 1000 mL of DCM. Bis(trifluoroacetoxy)iodobenzene (PIFA, 16.7 g, 38.8 mmol) was added in portions at room temperature. After stirring at room temperature for 2 days, the reaction mixture was concentrated to a suitable volume and filtered to obtain a black solid compound P3-115 (13.0 g, yield 83%). The product was identified as the target product with a molecular weight of 786.0.

[0263] Synthesis Example 5: Synthesis of Compound P3-124

[0264] Step 1: Synthesis of intermediate P3-124-A

[0265]

[0266] In a 2L two-necked flask, intermediates SM0 (11.5 g, 36.2 mmol), P3-124-SM1 (41.7 g, 120.5 mmol), potassium phosphate trihydrate (36.2 g, 136.2 mmol), Pd2(dba)3 (1.68 g, 1.832 mmol), and SPhos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 2.25 g, 5.48 mmol) were added sequentially. The mixture was purged with nitrogen three times. Under nitrogen protection, 800 mL of toluene and 200 mL of water were added, and the mixture was heated to 100 °C and reacted overnight. After the reaction was complete, the mixture was cooled, extracted with a suitable amount of tetrahydrofuran, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P3-124-A (19.5 g, 71% yield).

[0267] Step 2: Synthesis of intermediate P3-124-B

[0268]

[0269] In a 2L two-necked flask, intermediate P3-124-A (19.5 g, 25.7 mmol) was added. Under nitrogen protection, 800 mL of ultradry THF was added, and the mixture was cooled to -30 °C. Then, lithium bis(trimethylsilyl)amino (LiHMDS, 60 mL, 60 mmol) was added dropwise. The mixture was reacted at this temperature for 2 h. Then, elemental iodine (18.4 g, 72.3 mmol) was added, and the mixture was heated to room temperature for 0.5 h. The reaction was quenched with saturated sodium sulfite solution, extracted with an appropriate amount of ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P3-124-B (22.4 g, yield 86%).

[0270] Step 3: Synthesis of intermediate P3-124-C

[0271]

[0272] In a 2L two-necked flask, intermediate P3-124-B (22.4 g, 22.1 mmol), malononitrile (5.85 g, 88.6 mmol), potassium carbonate (12.8 g, 92.4 mmol), and Pd(PPh3)4 (0.326 g, 0.282 mmol) were added sequentially. Under nitrogen protection, 350 mL of DMF was added, and the mixture was heated to 80 °C and reacted overnight. After the reaction was complete, the mixture was cooled to room temperature and then cooled in an ice-water bath. The reaction solution was slowly added dropwise to 3N hydrochloric acid, resulting in the precipitation of a large amount of yellow solid. The crude product was filtered to obtain a white solid intermediate P3-124-C (16.1 g, 82% yield) by crystallization.

[0273] Step 4: Synthesis of compound P3-124

[0274]

[0275] Under a nitrogen atmosphere, intermediate P3-124-C (16.1 g, 18.1 mmol) was added to a 3 L single-necked flask, followed by 1000 mL of DCM. Bis(trifluoroacetoxy)iodobenzene (PIFA, 15.8 g, 36.8 mmol) was added in portions at room temperature. After stirring at room temperature for 2 days, the reaction mixture was concentrated to a suitable volume and filtered to obtain a black solid compound P3-124 (12.0 g, 75% yield). The product was identified as the target product with a molecular weight of 886.0.

[0276] Synthesis Example 6: Synthesis of Compound P3-128

[0277] Step 1: Synthesis of intermediate P3-128-A

[0278]

[0279] In a 2L two-necked flask, intermediates SM0 (10.2 g, 32.2 mmol), P3-128-SM1 (38.0 g, 91.8 mmol), potassium phosphate trihydrate (28.0 g, 105.2 mmol), Pd2(dba)3 (1.52 g, 1.654 mmol), and SPhos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 2.13 g, 5.19 mmol) were added sequentially. The mixture was purged with nitrogen three times. Under nitrogen protection, 800 mL of toluene and 200 mL of water were added, and the mixture was heated to 100 °C and reacted overnight. After the reaction was complete, the mixture was cooled, extracted with a suitable amount of tetrahydrofuran, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P3-128-A (18.8 g, 65% yield).

[0280] Step 2: Synthesis of intermediate P3-128-B

[0281]

[0282] In a 2L two-necked flask, intermediate P3-128-A (18.8 g, 20.9 mmol) was added. Under nitrogen protection, 800 mL of ultradry THF was added, and the mixture was cooled to -30 °C. Then, lithium bis(trimethylsilyl)amino (LiHMDS, 60 mL, 60 mmol) was added dropwise. The mixture was reacted at this temperature for 2 h. Then, elemental iodine (16.6 g, 65.3 mmol) was added, and the mixture was heated to room temperature for 0.5 h. The reaction was quenched with saturated sodium sulfite solution, extracted with an appropriate amount of ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P3-128-B (21.1 g, 88% yield).

[0283] Step 3: Synthesis of intermediate P3-128-C

[0284]

[0285] In a 2L two-necked flask, intermediate P3-128-B (21.1 g, 18.4 mmol), malononitrile (5.00 g, 75.8 mmol), potassium carbonate (11.2 g, 81.2 mmol), and Pd(PPh3)4 (0.229 g, 0.198 mmol) were added sequentially. Under nitrogen protection, 350 mL of DMF was added, and the mixture was heated to 80 °C and reacted overnight. After the reaction was complete, the mixture was cooled to room temperature and then cooled in an ice-water bath. The reaction solution was slowly added dropwise to 3N hydrochloric acid, resulting in the precipitation of a large amount of yellow solid. The crude product was filtered to obtain a white solid intermediate P3-128-C (13.6 g, 72% yield) by crystallization.

[0286] Step 4: Synthesis of compound P3-128

[0287]

[0288] Under a nitrogen atmosphere, intermediate P3-128-C (13.6 g, 13.2 mmol) was added to a 3 L single-necked flask, followed by 1000 mL of DCM. Bis(trifluoroacetoxy)iodobenzene (PIFA, 11.0 g, 25.6 mmol) was added in portions at room temperature. After stirring at room temperature for 2 days, the reaction mixture was concentrated to a suitable volume and filtered to obtain a black solid compound P3-128 (10.3 g, 78% yield). The product was identified as the target product with a molecular weight of 1022.0.

[0289] Synthesis Example 7: Synthesis of Compound P3-346

[0290] Step 1: Synthesis of intermediate P3-346-A

[0291]

[0292] In a 2L two-necked flask, intermediates SM0 (11.3 g, 35.4 mmol), P3-346-SM1 (45.1 g, 101.2 mmol), potassium phosphate trihydrate (31.4 g, 118.2 mmol), Pd2(dba)3 (1.72 g, 1.874 mmol), and SPhos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 3.36 g, 8.19 mmol) were added sequentially. The mixture was purged with nitrogen three times. Under nitrogen protection, 800 mL of toluene and 200 mL of water were added, and the mixture was heated to 100 °C and reacted overnight. After the reaction was complete, the mixture was cooled, extracted with a suitable amount of tetrahydrofuran, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P3-346-A (23.1 g, 68% yield).

[0293] Step 2: Synthesis of intermediate P3-346-B

[0294]

[0295] In a 2L two-necked flask, intermediate P3-346-A (23.1 g, 24.1 mmol) was added. Under nitrogen protection, 800 mL of ultradry THF was added, and the mixture was cooled to -30 °C. Then, lithium bis(trimethylsilyl)amino (LiHMDS, 60 mL, 60 mmol) was added dropwise. The mixture was reacted at this temperature for 2 h. Then, elemental iodine (16.3 g, 64.2 mmol) was added, and the mixture was heated to room temperature for 0.5 h. The reaction was quenched with saturated sodium sulfite solution, extracted with an appropriate amount of ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P3-346-B (24.5 g, 84% yield).

[0296] Step 3: Synthesis of intermediate P3-346-C

[0297]

[0298] In a 2L two-necked flask, intermediate P3-346-B (24.5 g, 20.2 mmol), malononitrile (5.18 g, 78.5 mmol), potassium carbonate (11.8 g, 85.2 mmol), and Pd(PPh3)4 (0.287 g, 0.248 mmol) were added sequentially. Under nitrogen protection, 350 mL of DMF was added, and the mixture was heated to 80 °C and reacted overnight. After the reaction was complete, the mixture was cooled to room temperature and then cooled in an ice-water bath. The reaction solution was slowly added dropwise to 3N hydrochloric acid, resulting in the precipitation of a large amount of yellow solid. The crude product was filtered to obtain a white solid intermediate P3-346-C (16.7 g, 76% yield) by crystallization.

[0299] Step 4: Synthesis of compound P3-346

[0300]

[0301] Under a nitrogen atmosphere, intermediate P3-346-C (16.7 g, 15.4 mmol) was added to a 3 L single-necked flask, followed by 1000 mL of DCM. Bis(trifluoroacetoxy)iodobenzene (PIFA, 13.7 g, 31.8 mmol) was added in portions at room temperature. After stirring at room temperature for 2 days, the reaction mixture was concentrated to a suitable volume and filtered to obtain a black solid compound P3-128 (11.4 g, yield 68%). The product was identified as the target product with a molecular weight of 1086.0.

[0302] Synthesis Example 8: Synthesis of Compound P4-109

[0303] Step 1: Synthesis of intermediate P4-109-A

[0304]

[0305] In a 2L two-necked flask, intermediates SM0 (10.3 g, 32.3 mmol), P4-109-SM1 (21.5 g, 106.2 mmol), potassium phosphate trihydrate (29.3 g, 110.2 mmol), Pd2(dba)3 (1.62 g, 1.764 mmol), and SPhos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 3.38 g, 8.24 mmol) were added sequentially. The mixture was purged with nitrogen three times. Under nitrogen protection, 800 mL of toluene and 200 mL of water were added, and the mixture was heated to 100 °C and reacted overnight. After the reaction was complete, the mixture was cooled, extracted with a suitable amount of tetrahydrofuran, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P4-109-A (11.3 g, 74% yield).

[0306] Step 2: Synthesis of intermediate P4-109-B

[0307]

[0308] In a 2L two-necked flask, intermediate P4-109-A (11.3 g, 23.9 mmol) was added. Under nitrogen protection, 800 mL of ultradry THF was added, and the mixture was cooled to -30 °C. Then, lithium bis(trimethylsilyl)amino (LiHMDS, 60 mL, 60 mmol) was added dropwise. The mixture was reacted at this temperature for 2 h. Then, elemental iodine (16.3 g, 64.2 mmol) was added, and the mixture was heated to room temperature for 0.5 h. The reaction was quenched with saturated sodium sulfite solution, extracted with an appropriate amount of ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P4-109-B (13.7 g, 79% yield).

[0309] Step 3: Synthesis of intermediate P4-109-C

[0310]

[0311] In a 2L two-necked flask, intermediate P4-109-B (13.7 g, 18.9 mmol), malononitrile (5.05 g, 76.5 mmol), potassium carbonate (11.6 g, 83.8 mmol), and Pd(PPh3)4 (0.328 g, 0.284 mmol) were added sequentially. Under nitrogen protection, 350 mL of DMF was added, and the mixture was heated to 80 °C and reacted overnight. After the reaction was complete, the mixture was cooled to room temperature and then cooled in an ice-water bath. The reaction solution was slowly added dropwise to 3N hydrochloric acid, resulting in the precipitation of a large amount of yellow solid. The crude product was filtered to obtain a white solid intermediate P4-109-C (8.40 g, 74% yield) by crystallization.

[0312] Step 4: Synthesis of compound P4-109

[0313]

[0314] Under a nitrogen atmosphere, intermediate P4-109-C (8.40 g, 14.0 mmol) was added to a 3 L single-necked flask, followed by 1000 mL of DCM. Bis(trifluoroacetoxy)iodobenzene (PIFA, 11.5 g, 26.8 mmol) was added in portions at room temperature. After stirring at room temperature for 2 days, the reaction mixture was concentrated to a suitable volume and filtered to obtain a black solid compound P4-109 (7.6 g, 91% yield). The product was identified as the target product with a molecular weight of 598.0.

[0315] Synthesis Example 9: Synthesis of Compound P4-128

[0316] Step 1: Synthesis of intermediate P4-128-A

[0317]

[0318] In a 2L two-necked flask, intermediates SM0 (10.6 g, 33.4 mmol), P4-128-SM1 (40.8 g, 98.5 mmol), potassium phosphate trihydrate (29.2 g, 109.8 mmol), Pd2(dba)3 (1.76 g, 1.924 mmol), and SPhos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 3.38 g, 8.24 mmol) were added sequentially. The mixture was purged with nitrogen three times. Under nitrogen protection, 800 mL of toluene and 200 mL of water were added, and the mixture was heated to 100 °C and reacted overnight. After the reaction was complete, the mixture was cooled, extracted with a suitable amount of tetrahydrofuran, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P4-128-A (19.5 g, 65% yield).

[0319] Step 2: Synthesis of intermediate P4-128-B

[0320]

[0321] In a 2L two-necked flask, intermediate P4-128-A (19.5 g, 21.7 mmol) was added. Under nitrogen protection, 800 mL of ultradry THF was added, and the mixture was cooled to -30 °C. Then, lithium bis(trimethylsilyl)amino (LiHMDS, 60 mL, 60 mmol) was added dropwise. The mixture was reacted at this temperature for 2 h. Then, elemental iodine (16.8 g, 66.2 mmol) was added, and the mixture was heated to room temperature for 0.5 h. The reaction was quenched with saturated sodium sulfite solution, extracted with an appropriate amount of ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P4-128-B (21.4 g, 86% yield).

[0322] Step 3: Synthesis of intermediate P4-128-C

[0323]

[0324] In a 2L two-necked flask, intermediate P4-128-B (21.4 g, 18.7 mmol), malononitrile (5.17 g, 78.4 mmol), potassium carbonate (12.3 g, 88.8 mmol), and Pd(PPh3)4 (0.310 g, 0.268 mmol) were added sequentially. Under nitrogen protection, 350 mL of DMF was added, and the mixture was heated to 80 °C and reacted overnight. After the reaction was complete, the mixture was cooled to room temperature and then cooled in an ice-water bath. The reaction solution was slowly added dropwise to 3N hydrochloric acid, resulting in the precipitation of a large amount of yellow solid. The crude product was filtered to obtain a white solid intermediate P4-128-C (13.8 g, 72% yield) by crystallization.

[0325] Step 4: Synthesis of compound P4-128

[0326]

[0327] Under a nitrogen atmosphere, intermediate P4-128-C (13.8 g, 13.5 mmol) was added to a 3 L single-necked flask, followed by 1000 mL of DCM. Bis(trifluoroacetoxy)iodobenzene (PIFA, 11.0 g, 25.6 mmol) was added in portions at room temperature. After stirring at room temperature for 2 days, the reaction mixture was concentrated to a suitable volume and filtered to obtain a black solid compound P4-128 (10.5 g, 76% yield). The product was identified as the target product with a molecular weight of 1022.0.

[0328] Synthesis Example 10: Synthesis of Compound P4-136

[0329] Step 1: Synthesis of intermediate P4-136-A

[0330]

[0331] In a 2L two-necked flask, intermediates SM0 (14.6 g, 45.9 mmol), P4-136-SM1 (50.8 g, 167.7 mmol), potassium phosphate trihydrate (42.7 g, 160.5 mmol), Pd2(dba)3 (1.85 g, 2.02 mmol), and SPhos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 4.23 g, 10.3 mmol) were added sequentially. The mixture was purged with nitrogen three times. Under nitrogen protection, 800 mL of toluene and 200 mL of water were added, and the mixture was heated to 100 °C and reacted overnight. After the reaction was complete, the mixture was cooled, extracted with a suitable amount of tetrahydrofuran, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P4-136-A (21.0 g, 68% yield).

[0332] Step 2: Synthesis of intermediate P4-136-B

[0333]

[0334] In a 2L two-necked flask, intermediate P4-136-A (21.0 g, 31.2 mmol) was added. Under nitrogen protection, 1200 mL of ultradry THF was added, and the mixture was cooled to -20 °C. Then, lithium bis(trimethylsilyl)amino (LiHMDS, 60 mL, 60 mmol) was added dropwise. The mixture was reacted at this temperature for 2 h. Then, elemental iodine (16.2 g, 63.6 mmol) was added, and the mixture was heated to room temperature for 0.5 h. The reaction was quenched with saturated sodium sulfite solution, extracted with an appropriate amount of ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P4-136-B (22.0 g, 76% yield).

[0335] Step 3: Synthesis of intermediate P4-136-C

[0336]

[0337] In a 2L two-necked flask, intermediate P4-136-B (22.0 g, 23.8 mmol), malononitrile (6.34 g, 96.3 mmol), potassium carbonate (14.2 g, 102.8 mmol), and Pd(PPh3)4 (0.34 g, 0.294 mmol) were added sequentially. Under nitrogen protection, 500 mL of DMF was added, and the mixture was heated to 80°C and reacted overnight. After the reaction was complete, the mixture was cooled to room temperature and then cooled in an ice-water bath. The reaction solution was slowly added dropwise to 3N hydrochloric acid, resulting in the precipitation of a large amount of yellow solid. The crude product was filtered to obtain a white solid intermediate P4-136-C (11.8 g, 62% yield) by crystallization.

[0338] Step 4: Synthesis of compound P4-136

[0339]

[0340] Under a nitrogen atmosphere, intermediate P4-136-C (11.8 g, 14.8 mmol) was added to a 3 L single-necked flask, followed by 1000 mL of DCM. Bis(trifluoroacetoxy)iodobenzene (PIFA, 8.77 g, 20.4 mmol) was added in portions at room temperature. After stirring at room temperature for 2 days, the reaction mixture was concentrated to a suitable volume and filtered to obtain a black solid compound P4-136 (10.1 g, 85% yield). The product was identified as the target product with a molecular weight of 800.1.

[0341] Synthesis Example 11: Synthesis of Compound P4-206

[0342] Step 1: Synthesis of intermediate P4-206-A

[0343]

[0344] In a 2L two-necked flask, intermediates SM0 (9.6 g, 30.2 mmol), P4-206-SM1 (52.5 g, 126.5 mmol), potassium phosphate trihydrate (31.3 g, 117.5 mmol), Pd2(dba)3 (1.45 g, 1.58 mmol), and SPhos (2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, 3.56 g, 8.67 mmol) were added sequentially. The mixture was purged with nitrogen three times. Under nitrogen protection, 800 mL of toluene and 200 mL of water were added, and the mixture was heated to 100 °C and reacted overnight. After the reaction was complete, the mixture was cooled, extracted with a suitable amount of tetrahydrofuran, dried over anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain a white solid intermediate P4-206-A (12.5 g, 46% yield).

[0345] Step 2: Synthesis of intermediate P4-206-B

[0346]

[0347] In a 2L two-necked flask, intermediate P4-206-A (12.5 g, 13.9 mmol) was added. Under nitrogen protection, 800 mL of ultra-dry THF was added, and the temperature was lowered to -30°C. Then, lithium bis(trimethylsilyl)amino (LiHMDS, 50 mL, 50 mmol) was added dropwise. The reaction was carried out at this temperature for 2 h. Then, elemental iodine (14.9 g, 58.6 mmol) was added, and the reaction was raised to room temperature for 0.5 h. The reaction was quenched with saturated sodium sulfite solution, extracted with an appropriate amount of ethyl acetate, dried with anhydrous magnesium sulfate, concentrated, and purified by column chromatography to obtain white solid intermediate P4-206-B (14.4 g, 90% yield).

[0348] Step 3: Synthesis of intermediate P4-206-C

[0349]

[0350] Potassium (7.44 g, 53.8 mmol) and Pd(PPh3)4 (0.25 g, 0.216 mmol) were added to 350 mL of DMF under nitrogen protection, and the mixture was heated to 80 °C and reacted overnight. After the reaction was complete, the mixture was cooled to room temperature and then cooled in an ice-water bath. The reaction solution was slowly added dropwise to 3N hydrochloric acid, resulting in the precipitation of a large amount of yellow solid. The crude product was filtered to obtain a white solid intermediate, P4-206-C (10.4 g, yield 81%), which was obtained by crystallization.

[0351] Step 4: Synthesis of compound P4-206

[0352]

[0353] Under a nitrogen atmosphere, intermediate P4-206-C (10.4 g, 10.1 mmol) was added to a 3 L single-necked flask, followed by 1000 mL of DCM. Bis(trifluoroacetoxy)iodobenzene (PIFA, 7.14 g, 16.6 mmol) was added in portions at room temperature. After stirring at room temperature for 2 days, the reaction mixture was concentrated to a suitable volume and filtered to obtain a black solid compound P4-206 (5.80 g, yield 56%). The product was identified as the target product with a molecular weight of 1024.0.

[0354] Comparative compounds

[0355]

[0356] Device Examples

[0357] Device Example 1

[0358] This embodiment provides an organic electroluminescent device, the fabrication method of which is as follows: An ITO substrate is patterned to have a light-emitting area of ​​2mm × 2mm, then washed with isopropanol, UV, and ozone respectively. Afterwards, the ITO substrate is mounted on a substrate support of a vacuum deposition apparatus, and the pressure is adjusted to make the vacuum rate 1 × 10⁻⁶. -7First, a hole injection layer is formed on the ITO layer (anode) formed on the substrate by vacuum deposition of compounds P1-493 and HT-1 (mass ratio of compound P1-493 to compound HT-1 is 2:98) provided in Synthesis Example 1 of the present invention, with a thickness of 10 nm. Next, a hole transport layer is formed on the hole injection layer by vacuum deposition of compound HT-1 with a thickness of 110 nm. Then, an electron blocking layer is formed on the hole transport layer by vacuum deposition of compound EB-1 with a thickness of 10 nm. Finally, a hole transport layer is formed on the electron blocking layer by vacuum deposition of compound BD-1 with a thickness of 20 nm. A light-emitting layer is formed by a mixture of BD-1 and compound BH (mass ratio of BD-1 to BH is 2:98); then, a hole-blocking layer is formed by vacuum depositing compound HB-1 with a thickness of 5 nm on the light-emitting layer; next, an electron transport layer is formed by vacuum depositing compound ET-1 and compound Liq (mass ratio of ET-1 to Liq is 5:5) with a thickness of 30 nm on the hole-blocking layer; then, an electron injection layer is formed by depositing LiF with a thickness of 1 nm on the electron transport layer; finally, an electron cathode is formed by depositing aluminum (Al) with a thickness of 150 nm on the electron injection layer, thus preparing a cathode as shown in the figure. Figure 1 The organic electroluminescent device shown.

[0359] Device Example 2

[0360] The preparation method is the same as in Device Example 1, except that compound P1-493 in the hole injection layer is replaced with compound P2-257, and the mass ratio of compound P2-257 to HT-1 in the hole injection layer is 2:98.

[0361] Device Example 3

[0362] The preparation method is the same as in Device Example 1, except that compound P1-493 in the hole injection layer is replaced with compound P2-271, and the mass ratio of compound P2-271 to HT-1 in the hole injection layer is 2:98.

[0363] Device Example 4

[0364] The preparation method is the same as in Device Example 1, except that compound P1-493 in the hole injection layer is replaced with compound P3-115, and the mass ratio of compound P3-115 to HT-1 in the hole injection layer is 2:98.

[0365] Device Example 5

[0366] The preparation method is the same as in Device Example 1, except that compound P1-493 in the hole injection layer is replaced with compound P3-124, and the mass ratio of compound P3-124 to HT-1 in the hole injection layer is 2:98.

[0367] Device Example 6

[0368] The preparation method is the same as in Device Example 1, except that compound P1-493 in the hole injection layer is replaced with compound P3-128, and the mass ratio of compound P3-128 to HT-1 in the hole injection layer is 2:98.

[0369] Device Example 7

[0370] The preparation method is the same as in Device Example 1, except that compound P1-493 in the hole injection layer is replaced with compound P3-346, and the mass ratio of compound P3-346 to HT-1 in the hole injection layer is 2:98.

[0371] Device Example 8

[0372] The preparation method is the same as in Device Example 1, except that compound P1-493 in the hole injection layer is replaced with compound P4-109, and the mass ratio of compound P4-109 to HT-1 in the hole injection layer is 2:98.

[0373] Device Example 9

[0374] The preparation method is the same as in Device Example 1, except that compound P1-493 in the hole injection layer is replaced with compound P4-128, and the mass ratio of compound P4-128 to HT-1 in the hole injection layer is 2:98.

[0375] Device Example 10

[0376] The preparation method is the same as in Device Example 1, except that compound P1-493 in the hole injection layer is replaced with compound P4-136, and the mass ratio of compound P4-136 to HT-1 in the hole injection layer is 2:98.

[0377] Device Example 11

[0378] The preparation method is the same as in Device Example 1, except that compound P1-493 in the hole injection layer is replaced with compound P4-206, and the mass ratio of compound P4-206 to HT-1 in the hole injection layer is 2:98.

[0379] Device Comparison Example 1

[0380] The preparation method is the same as in Device Example 1, except that compound P1-493 in the hole injection layer is replaced with compound PD-1, and the mass ratio of compound PD-1 to HT-1 in the hole injection layer is 2:98.

[0381] Device Comparison Example 2

[0382] The preparation method is the same as in Device Example 1, except that compound P1-493 in the hole injection layer is replaced with compound PD-2, and the mass ratio of compound PD-2 to HT-1 in the hole injection layer is 2:98.

[0383] Device Comparison Example 3

[0384] The preparation method is the same as in Device Example 1, except that compound P1-493 in the hole injection layer is replaced with compound PD-3, and the mass ratio of compound PD-3 to HT-1 in the hole injection layer is 2:98.

[0385] The molecular structural formulas of the materials used in this invention and the remaining layers of the device are as follows:

[0386]

[0387] The electrode preparation method and the deposition method of each functional layer in this embodiment are conventional methods in the art, such as vacuum thermal evaporation or inkjet printing, and will not be described in detail here.

[0388] Device performance

[0389] The organic electroluminescent devices provided in Device Examples 1-11 and Comparative Examples 1-3 were tested using standard methods. For this purpose, J = 10 mA / cm² was used. 2 The driving voltage and current efficiency (CE) of the organic electroluminescent device were determined at a current density of J = 25 mA / cm². 2 The lifetime (LT95) of the organic electroluminescent device was determined at a given current density.

[0390] The testing instruments and methods used to perform performance testing on the above-mentioned OLED devices are as follows:

[0391] Brightness was tested using a PhotoResearch PR-635 spectral scanner;

[0392] Current density and turn-on voltage: tested using a Keithley 2400 digital source meter;

[0393] Lifetime testing: Using a silicon photonics-based OLED device lifetime testing system.

[0394] The performance test results of the above devices are listed in Table 5.

[0395] Table 5 Device performance test results

[0396]

[0397]

[0398] The device performance test results in Table 5 above show that:

[0399] The organic electroluminescent devices prepared by the organic compounds provided by the present invention in Examples 1-11 have a lower driving voltage than those in Comparative Example 1, while having comparable current efficiency and lifetime, indicating that the organic compounds of the present invention have excellent hole injection capability as hole injection layer doping materials.

[0400] Meanwhile, TGA testing showed that the organic compounds provided by this invention have better heat resistance and thermal stability than PD-1. For example, TGA testing of P3-115 showed a 5% weight loss temperature of 385°C, TGA testing of P2-271 showed a 5% weight loss temperature of 380°C, while TGA testing of PD-1 showed a 5% weight loss temperature of 346°C. A higher weight loss temperature indicates better molecular heat resistance and thermal stability.

[0401] Compared with the organic electroluminescent devices provided in Comparative Examples 2 and 3, the organic electroluminescent devices prepared with organic compounds provided by the present invention in Examples 1-11 all show varying degrees of improvement in driving voltage, current efficiency, and lifetime. Specifically, compared with the organic electroluminescent device provided in Comparative Example 2, the driving voltage of the organic electroluminescent devices prepared with organic compounds provided by the present invention in Examples 1-11 is reduced by 8.4% to 14.9%, the current efficiency is increased by 6.5% to 11.1%, and the lifetime is increased by 36.8% to 42.7%. Compared with the organic electroluminescent device provided in Comparative Example 3, the driving voltage of the organic electroluminescent devices prepared with organic compounds provided by the present invention in Examples 1-11 is reduced by 5.3% to 12.0%, the current efficiency is increased by 16.8% to 21.8%, and the lifetime is increased by 30.3% to 36.0%. This indicates that the two X rings of Formula II unit in the compound structure of the present invention can better improve the doping ability of the material in the hole injection layer than a single OCF3, thereby reducing the device voltage and improving the device efficiency and lifetime.

[0402] Sublimation thermal stability test:

[0403] The materials from the synthetic examples and comparative examples (PD-1 to PD-5) of this invention were evenly spread in a vacuum sublimation apparatus, and the pressure was adjusted to make the vacuum rate 1×10⁻⁶. -5 Below torr; use a programmed heating method to gradually increase the temperature until material is deposited in the collection area of ​​the vacuum sublimation apparatus, then stop heating and keep the temperature constant; after a certain period of time, confirm that the material in the collection area of ​​the vacuum sublimation apparatus is no longer increasing, stop heating, slowly cool down, and collect the sublimated material in the collection area of ​​the vacuum sublimation apparatus.

[0404] The structures of the two newly added comparative compounds, PD-4 and PD-5, are shown below:

[0405]

[0406] The results of the above sublimation performance tests are listed in Table 6.

[0407] Table 6 Sublimation Test Results

[0408]

[0409]

[0410] The results above show that the purity of the organic compound material of the present invention changes by ±0.3% before and after sublimation, indicating little change in purity. In some cases, the purity not only does not decrease but even increases. The purity change of the organic compound material provided by the present invention before and after sublimation is basically equivalent to that of PD-1. In contrast, the purity of the comparative materials PD-2 to PD-5 decreased to varying degrees after sublimation. Although PD-2 and PD-3 have only two OCF3 groups, their purity decreased by 0.3% and 0.4% after sublimation, respectively. In contrast, PD-4 and PD-5 have four OCF3 groups, and their purity decreased by 4.0% and 2.1% after sublimation. The significant decrease in purity makes the materials unsuitable for device evaluation. It can be seen that the two X groups in Formula II of the organic compound of the present invention, which are in one ring, make the compound structure more stable and have better heat resistance.

[0411] The organic compounds of the present invention exhibit sublimation yields ranging from 55% to 86%, demonstrating excellent sublimation production. Compared to PD-5, the sublimation yield of the organic compound P4-109 of the present invention is increased by 32%, indicating that when the benzene ring substitution positions are consistent, the cyclization of structure X in formula II of the compounds of the present invention is beneficial to material stability and increases sublimation yield. Compared to PD-3, the sublimation yield of the organic compound P4-109 of the present invention is approximately 2% higher, and the compounds of the present invention still exhibit high sublimation yields. The organic compound P2-257 of the present invention has comparable sublimation yields to the comparative compound PD-1. Compared to organic compounds P2-257 and P4-109, the other compounds of the present invention, particularly those with the L linker in formula II, show significantly increased sublimation yields of 15% to 31%.

[0412] In summary, the organic compounds provided by this invention have excellent hole injection layer doping capabilities, and the organic electroluminescent devices prepared using the organic compounds of this invention have excellent device performance. At the same time, their unique ring structure not only improves the thermal stability of the material, but also enhances the sublimation yield of the material, and has broad application value.

[0413] The above description is merely a preferred embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any variations or substitutions that can be easily conceived by those skilled in the art within the scope of the technology disclosed in the present invention should be included within the scope of protection of the present invention. Therefore, the scope of protection of the present invention should be determined by the scope of the claims.

Claims

1. A compound for use in organic electroluminescent devices, characterized in that, The general structural formula of the compound is shown in Formula I: In Formula I, W is independently selected from O, S, or Se; Ar 1 Ar 2 Each is independently selected from the group consisting of: hydrogen, deuterium, halogen, carbonyl, cyano, sulfinyl, sulfonyl, phosphoxy, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms; and Ar 1 Ar 2 At least one of them has the structure shown in Equation II. In Equation II, X is independently selected from O, S, and Se. Any one or any combination of them; L is selected from single bond, O, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof; Ring A is selected from any one of substituted or unsubstituted aromatic rings having 6-30 carbon atoms, or substituted or unsubstituted heteroaromatic rings having 3-30 carbon atoms; R 3 The substituents representing ring A are selected from monosubstituted, polysubstituted, or unsubstituted groups, when R 3 When there is multiple substitution, the multiple substituents can be the same or different; R 1 R 2 R 3 Each group is independently selected from the following groups: hydrogen, deuterium, hydroxyl, mercapto, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phosphooxy, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted... The following are any one or any combination of aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, and substituted or unsubstituted amino groups having 0-20 carbon atoms. R' and R” are each independently selected from the group consisting of: hydroxyl, mercapto, halogen, nitroso, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, SCN, OCN, SF5, sulfinyl, sulfonyl, phosphooxy, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, and substituted or unsubstituted heterocyclic with 3-20 ring atoms. The group consists of any one or any combination of several of the following: alkyl, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aroxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, and substituted or unsubstituted heteroaryl having 3-30 carbon atoms. The Ar 1 Ar 2 At least one of R' and R" contains at least one electron-withdrawing group; the Ar 1 Ar 2 ,R',R”R 1 R 2 R 3 In L, any adjacent substituents can bond with each other to form a ring; * indicates the connection position of L with formula I, and * indicates the connection position of X with other groups.

2. The compound according to claim 1, characterized in that, The compound has the structure shown in Formula I-1: The R', R", R 1 R 2 R 3 In L, any adjacent substituents can bond with each other to form a ring.

3. The compound according to claim 1, characterized in that, The compound has the structure shown in Formula I-2: The R 1 R 2 R 3 In L, any adjacent substituents can bond with each other to form a ring.

4. The compound according to claim 1, characterized in that, The structure shown in Formula II is selected from one of the structures shown in Formula II-1 to Formula II-6: Among them, Z is selected from CR each time it appears, either the same or different. 3 Or N; In equations II-1 to II-6, X is independently selected from O, S, and Se. Any one or any combination of them; L, each time appearing, is selected from single bond, O, substituted or unsubstituted aryl group with 6-30 carbon atoms, substituted or unsubstituted heteroaryl group with 3-30 carbon atoms, and combinations thereof; R 1 R 2 R 3 Each time it appears, it is selected from the group consisting of the following groups, either identically or differently: hydrogen, deuterium, hydroxyl, mercapto, halogen, nitrosyl, nitro, acyl, carbonyl, carboxylic acid, ester, cyano, isocyanate, SCN, OCN, SF5, borane, sulfinyl, sulfonyl, phospho, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 ring carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted heterocyclic with 3-20 ring atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, etc. The following are substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alksilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted alkylgermanium groups having 3-20 carbon atoms, substituted or unsubstituted arylgermanium groups having 6-20 carbon atoms, substituted or unsubstituted amino groups having 0-20 carbon atoms, and combinations thereof. The R 1 R 2 R 3 In this process, any adjacent substituents can bond with each other to form a ring; * indicates the connection position of L with formula I, and * indicates the connection position of X with other groups.

5. The compound according to claim 4, characterized in that, The structure shown in Formula II is selected from the structure shown in Formula II-1 or Formula II-2.

6. The compound according to claim 1, characterized in that, The R 1 R 2 Each is independently selected from the group consisting of: hydrogen, deuterium, halogen, nitroso, nitro, carbonyl, cyano, SF5, sulfinyl, sulfonyl, phosphoxy, substituted or unsubstituted alkyl having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl having 1-20 carbon atoms, substituted or unsubstituted heterocyclic having 3-20 cyclic atoms, substituted or unsubstituted aralkyl having 7-30 carbon atoms, substituted or unsubstituted alkoxy having 1-20 carbon atoms, substituted or unsubstituted aroxy having 6-30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, and substituted or unsubstituted heteroaryl having 3-30 carbon atoms, or any combination of any of these groups. The R 1 R 2 In this process, any adjacent substituents can bond with each other to form a ring.

7. The compound according to claim 1, characterized in that, The W is selected from O; and / or The R' and R" are selected, in the same or different manner each time they appear, from the group consisting of: fluorine, cyano, SCN, sulfonyl, substituted or unsubstituted alkyl with 1-20 carbon atoms, substituted or unsubstituted cycloalkyl with 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl with 1-20 carbon atoms, substituted or unsubstituted aralkyl with 7-30 carbon atoms, substituted or unsubstituted alkoxy with 1-20 carbon atoms, substituted or unsubstituted aroxy with 6-30 carbon atoms, substituted or unsubstituted aryl with 6-30 carbon atoms, and substituted or unsubstituted heteroaryl with 3-30 carbon atoms; and / or R 1 R 2 Each time it appears, it is selected from the group consisting of the same or different groups of the following: hydrogen, deuterium, fluorine, carbonyl, cyano, SF5, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, and combinations thereof.

8. The compound according to claim 1, characterized in that, X is selected from O; and / or At least one of R' and R" is selected from cyano.

9. The compound according to claim 1, characterized in that, When ring A has substituents, ring A can be represented by one or more R groups each time it appears. 3 Substitution, when L has substituents, L can be replaced by one or more R each time it appears. 4 replace; The R 3 R 4 Each occurrence may be selected, either identically or differently, from the group consisting of: hydrogen, deuterium, hydroxyl, mercapto, halogen, carbonyl, cyano, SF5, sulfonyl, phosphoxy, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 cyclic carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aroxy groups having 6-30 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms; any combination of one or more of the following: adjacent R 3 R 4 They can be arbitrarily connected to form a ring.

10. The compound according to claim 1, characterized in that, L, each time appearing, is selected from any one or any combination of single bond, O, substituted or unsubstituted phenylene, substituted or unsubstituted pyridylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted naphthinylene, substituted or unsubstituted phenanthrolinel, substituted or unsubstituted anthracene, substituted or unsubstituted fluorene, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted carbazolyl.

11. The compound according to claim 9, characterized in that, L is selected, either identically or differently, from single bonds, O, and the following structures, and combinations thereof: In the above-mentioned compounds, hydrogen may be partially or completely replaced by deuterium; "..." indicates the connection position of L with formula I or other L, and "..." indicates the connection position of L with ring A or other L.

12. The compound according to claim 11, characterized in that, Ar 1 Ar 2 ,R',R”R 1 R 2 R 3 R 4 Each occurrence is either identical or different from the group consisting of the following structures: In the above-mentioned compounds, hydrogen may be partially or completely replaced by deuterium; This indicates the connection points between the above structure and other structures.

13. The compound according to claim 12, characterized in that, The organic compounds are selected from the group consisting of compounds P1-1 to P1-1028, compounds P2-1 to P2-1028, compounds P3-1 to P3-1028, and compounds P4-1 to P4-1028. The compounds P1-1 to P1-1028 have structures represented by formula I-1-1; wherein R 1 R 2 Similarly, the W and Ar mentioned above 1 R 1 R 2 X and L correspond to atoms or groups selected from the table below: The compounds P2-1 to P2-1028 have structures represented by formula I-1-2; wherein R 1 R 2 Similarly, the W and Ar mentioned above 1 R 1 R 2 X and L correspond to atoms or groups selected from the table below: The compounds P3-1 to P3-1028 have structures represented by formula I-2-1; wherein R 1 R 2 The same applies to W, Z, and R. 1 R 2 X and L correspond to atoms or groups selected from the table below: The compounds P4-1 to P4-1028 have structures represented by formula I-2-2; wherein R 1 R 2 The same applies to W, Z, and R. 1 R 2 X and L correspond to atoms or groups selected from the table below: In the above-mentioned compounds, hydrogen may be partially or completely replaced by deuterium.

14. An organic electroluminescent device, characterized in that, include: anode, cathode, And an organic layer disposed between the anode and the cathode, wherein the organic layer comprises any one of claims 1 to 13.

15. The organic electroluminescent device as described in claim 14, characterized in that, The organic layer is a hole injection layer or a hole transport layer, and the hole injection layer or hole transport layer is formed solely by the compound of any one of claims 1 to 13.

16. The electroluminescent device as described in claim 14, characterized in that, The organic layer is a hole injection layer or a hole transport layer, and the hole injection layer or hole transport layer further comprises at least one hole transport material; the mass doping ratio of the organic compound to the at least one hole transport material is 10:1 to 1:

100.

17. The organic electroluminescent device as described in claim 14, characterized in that, The organic electroluminescent device includes at least two light-emitting units, and the organic layer is a charge-generating layer disposed between the at least two light-emitting units, wherein the charge-generating layer includes a p-type charge-generating layer and an n-type charge-generating layer; The p-type charge generation layer comprises any one of claims 1 to 13; The p-type charge generation layer further comprises at least one hole transport material, wherein the mass doping ratio of the organic compound to the at least one hole transport material is from 10:1 to 1:

100.

18. The organic electroluminescent device as described in claim 17, characterized in that, The charge-generating layer further includes a buffer layer disposed between the p-type charge-generating layer and the n-type charge-generating layer, the buffer layer comprising the compound of any one of claims 1 to 13.

19. A display component, characterized in that, The display component comprises the organic electroluminescent device according to any one of claims 14 to 18.

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