Organic compounds containing triazines and pyrimidines and uses thereof

Abstract

The application discloses a triazine and pyrimidine-containing organic compound and application thereof, and belongs to the technical field of semiconductor materials. The structure of the compound is shown in general formula (1). The compound has good stability and electron resistance, and has good electron injection and electron transmission capacity. Furthermore, the compound has excellent thin film stability, can inhibit phase change of the material at high temperature, and prevents phase state separation or decomposition of the material. When the compound is used as a material of an organic electroluminescent device, the device voltage and the device life are effectively improved, and in particular, the high-temperature device life is obviously improved.

Description

Technical Field

[0001] This invention relates to the field of semiconductor materials technology, and in particular to an organic compound containing triazine and pyrimidine and its applications. Background Technology

[0002] Organic Light Emission Diodes (OLEDs) technology can be used to manufacture novel display products and lighting products, and is expected to replace existing liquid crystal displays and fluorescent lighting, with a very wide range of applications. OLED devices have a sandwich-like structure, including electrode material layers and organic functional materials sandwiched between different electrode material layers. Various organic functional materials are stacked together according to their intended use to form the OLED light-emitting device. As a current-emitting device, when a voltage is applied to its two electrodes, and an electric field is applied to the positive and negative charges in the organic functional material layers, the positive and negative charges recombine in the light-emitting layer, thus generating OLED electroluminescence.

[0003] Currently, OLED display technology has been applied in smartphones, tablets, and other fields, and will further expand into large-screen applications such as televisions. However, compared with the requirements of actual product applications, the luminous efficiency and lifespan of OLED devices still need further improvement. In order to continuously improve the performance of OLED devices, continuous research and innovation in OLED optoelectronic functional materials are needed to create higher-performance OLED functional materials.

[0004] OLED optoelectronic functional materials used in OLED devices can be broadly categorized into two types based on their applications: charge injection transport materials and luminescent materials. Further, charge injection transport materials can be classified into electron injection transport materials, electron blocking materials, hole injection transport materials, and hole blocking materials. As charge transport materials, they require excellent carrier mobility and high glass transition temperature. In OLED devices, electrons are injected from the cathode and then transported through the electron transport layer to the host material, where they recombine with holes to generate excitons. Therefore, improving the injection and transport capabilities of the electron transport layer helps reduce the device driving voltage while achieving high electron-hole recombination efficiency. Thus, the electron transport layer is crucial, requiring high electron injection and transport capabilities as well as high electron durability.

[0005] With the significant advancements in OLED devices, the performance requirements for materials have also increased. These materials must not only possess excellent stability but also achieve good efficiency and lifespan at low driving voltages. However, current electron transport materials suffer from insufficient electron injection and transport capabilities, as well as inadequate thermal stability. Furthermore, defects in the electronic tolerance of these materials lead to phase separation or decomposition during device operation, resulting in poor device lifespan. Summary of the Invention

[0006] To address the aforementioned problems in the prior art, this invention provides a compound containing triazine and pyrimidine groups and its application in organic electroluminescent devices. The compound of this invention bridges the pyrimidine and triazine structures through a biphenyl group substituted with a fused-ring aryl or heteroaryl group. The pyrimidine is attached to the 1-position of the biphenyl group, the fused-ring aryl or heteroaryl group is attached to the 3-position of the biphenyl group, and the triazine is attached to the 5-position of the biphenyl group. The bridging group is a biphenyl group connected by a fused-ring aryl group.

[0007] By restricting the connection sites of triazine and pyrimidine through the above-mentioned linkage sites and introducing linking groups with fused-ring aryl groups, not only can the planar arrangement and stacking of molecules be effectively improved and the electron mobility of materials be enhanced, but also the charge tolerance and film stability of molecules can be effectively improved, the phase transition of materials at high temperatures can be suppressed, and the phase separation or decomposition of materials can be prevented, thereby effectively improving the lifespan of high-temperature devices.

[0008] The technical solution of this invention is as follows:

[0009] An organic compound containing triazine and pyrimidine, the structure of which is shown in general formula (1):

[0010]

[0011] In general formula (1), R1 is independently represented as one of naphthyl, pyridyl, quinolinyl, isoquinolinyl, biphenyl, phenanthryl, dibenzofuranyl, furanyl, benzofuranyl or carbazoleyl;

[0012] R2 and R3 are independently represented as phenyl, naphthyl, or biphenyl;

[0013] X1 and X2 are independent tables, either C or N, and X1 and X2 have exactly one representation as N.

[0014] The structure of the organic compound is shown in any one of general formulas (2-1) to (2-2):

[0015]

[0016] In general formulas (2-1) to (2-2)

[0017] R1 can be independently represented as one of naphthyl, pyridyl, quinolinyl, isoquinolinyl, biphenyl, phenanthryl, dibenzofuranyl, furanyl, benzofuranyl or carbazoleyl;

[0018] R2 and R3 are independently represented as phenyl, naphthyl, or biphenyl.

[0019] The structure of the organic compound is shown in any of general formulas (3-1) to (3-4):

[0020]

[0021] In general formulas (3-1) to (3-4)

[0022] R2 and R3 are independently represented as phenyl, naphthyl, or biphenyl.

[0023] Preferably, R3 represents phenyl or biphenyl.

[0024] Preferably, R2 represents phenyl or biphenyl.

[0025] Preferably, R1 is represented by the following structure:

[0026]

[0027] R2 and R3 are each independently represented as shown in the following structure:

[0028]

[0029] Preferably, the organic compound has any one of the following structures:

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039] An organic electroluminescent device includes a first electrode and a second electrode, wherein a multilayer organic thin film layer is provided between the first electrode and the second electrode, and at least one organic thin film layer contains the organic compound containing triazine and pyrimidine.

[0040] In a preferred embodiment, the organic thin film layer includes an electron transport layer containing the triazine and pyrimidine-containing organic compound.

[0041] An organic electroluminescent device comprises, in sequence, a first electrode, a hole transport region, a light-emitting region, an electron transport region, and a second electrode, wherein the electron transport region contains the organic compound containing triazine and pyrimidine.

[0042] In a preferred embodiment, the electron transport region includes an electron transport layer and a hole blocking layer.

[0043] In a preferred embodiment, the electron transport region includes an electron transport layer containing the triazine and pyrimidine-containing organic compound.

[0044] In a preferred embodiment, the electron transport layer contains Liq and the organic compound containing triazine and pyrimidine.

[0045] A display element comprising the aforementioned organic electroluminescent device.

[0046] The beneficial technical effects of this invention are as follows:

[0047] The compounds of this invention bridge the pyrimidine and triazine structures via a biphenyl group substituted with a fused-ring aryl or heteroaryl group. The pyrimidine is attached to one phenyl group on one side of the biphenyl group, and the triazine is attached to the other phenyl group on the other side of the biphenyl group, with fixed attachment sites. Specifically, the pyrimidine is attached to the 1-position of the biphenyl group, the fused-ring aryl or heteroaryl group is attached to the 3-position of the biphenyl group, and the triazine group is attached to the 5-position of the biphenyl group.

[0048] 1) It effectively improves the electronic tolerance of molecules. By linking the sites of biphenyl, it can effectively suppress the active groups of biphenyl, expand the delocalization range of electrons, reduce the electron enrichment of materials, and thus effectively improve the electronic tolerance of molecules.

[0049] 2) It effectively suppresses intermolecular interactions and molecular stacking, thereby suppressing electron quenching effects and improving the electroexcitation stability of molecules.

[0050] 3) The introduction of a fused-ring aryl or heteroaryl group at position 3 can form a spatial electronic resonance effect with the pyrimidine group at position 1 and the triazine group at position 3, which enhances the weak coupling interaction within the molecule, makes the electron distribution range wider, effectively reduces the electron concentration, and improves the stability of the molecule.

[0051] 4) By restricting the above-mentioned linking sites of triazine and pyrimidine, and introducing linking groups with fused ring aryl groups, it is possible not only to effectively improve the planar arrangement and stacking of molecules and enhance the electron mobility of materials, but also to effectively improve the charge tolerance and film stability of molecules, suppress phase transitions of materials at high temperatures, and prevent phase separation or decomposition of materials, thereby effectively improving the lifespan of high-temperature devices. Attached Figure Description

[0052] Figure 1 This is a schematic diagram of the structure of an OLED device using the materials listed in this invention.

[0053] In the figure, 1 is the transparent substrate layer, 2 is the anode layer, 3 is the hole injection layer, 4 is the hole transport layer, 5 is the electron blocking layer, 6 is the light-emitting layer, 7 is the hole blocking layer, 8 is the electron transport layer, 9 is the electron injection layer, 10 is the cathode layer, and 11 is the CPL layer.

[0054] Figure 2 The 1H NMR spectrum of compound 2. Detailed Implementation

[0055] The technical solution of the present invention will be described in detail below with reference to the accompanying drawings and embodiments.

[0056] In the accompanying drawings, for clarity, the dimensions of layers and regions may be exaggerated. It will also be understood that when a layer or element is referred to as being "above" another layer or substrate, the layer or element may be directly above that other layer or substrate, or intermediate layers may be present. Furthermore, it will be understood that when a layer is referred to as being "between" two layers, the layer may be the only layer between the two layers, or one or more intermediate layers may be present. The same reference numerals throughout the drawings denote the same elements.

[0057] In this application, the terms "upper" and "lower," used to indicate orientation when describing electrodes, organic electroluminescent devices, and other structures, only indicate orientation in a specific state and do not imply that the related structures can only exist in the stated orientation. Conversely, if the structure can be repositioned, such as by inverting it, the orientation of the structure will change accordingly. Specifically, in this invention, the "lower" side of the electrode refers to the side of the electrode closer to the substrate during fabrication, while the opposite side farther from the substrate is the "upper" side.

[0058] Organic electroluminescent devices

[0059] In another embodiment of this application, an organic electroluminescent device is provided, comprising a first electrode (anode), a second electrode (cathode), and a multilayer organic thin film layer located between the first electrode and the second electrode, wherein at least one organic thin film layer contains the organic compound containing the triazine and pyrimidine structure.

[0060] In a preferred embodiment of this application, the organic thin film layer includes an electron transport layer, wherein the electron transport layer contains an organic compound containing a triazine and pyrimidine structure according to the present invention.

[0061] Preferably, in addition to the organic compounds of the present invention, the electron transport layer also comprises other electron transport materials, such as Liq (see examples for specific chemical structures).

[0062] In a preferred embodiment of the present invention, the organic electroluminescent device according to the present invention includes a substrate, a first electrode layer (anode layer), an organic thin film layer, and a second electrode layer (cathode layer), wherein the organic thin film layer includes, but is not limited to, a light-emitting layer and a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron blocking layer and / or an electron injection layer.

[0063] The preferred device structure of this invention adopts a top-emitting form. Preferably, the anode of the organic electroluminescent device of this invention is an electrode with high reflectivity, preferably ITO / Ag / ITO; the cathode is a transparent electrode, preferably a mixed electrode of Mg:Ag = 1:9, thereby forming a microcavity resonance effect, and the device emits light from the Mg:Ag electrode side.

[0064] In a preferred embodiment of the present invention, an organic electroluminescent device is provided, comprising a substrate, an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode layer, wherein the anode is on the substrate, the hole injection layer is on the anode, the hole transport layer is on the hole injection layer, the electron blocking layer is on the hole transport layer, the light-emitting layer is on the hole transport layer, the electron transport layer is on the light-emitting layer, the electron injection layer is on the electron transport layer, and the cathode layer is on the electron injection layer.

[0065] As the substrate for the organic electroluminescent device of this invention, any substrate commonly used in organic electroluminescent devices can be used. Examples include transparent substrates, such as glass or transparent plastic substrates; opaque substrates, such as silicon substrates; and flexible PI film substrates. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance. Their application varies depending on their properties. In this invention, a transparent substrate is preferred. There are no particular limitations on the thickness of the substrate.

[0066] A first electrode (anode) is formed on a substrate. The anode material is preferably a material with a high work function to facilitate hole injection into the organic functional material layer. Non-limiting examples of anode materials include, but are not limited to, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). The first electrode can have a single-layer structure or a multilayer structure comprising two or more layers. For example, the anode can have a three-layer structure of ITO / Ag / ITO, but is not limited thereto. In addition, the thickness of the anode depends on the material used, typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0067] Hole injection layer 3, hole transport layer 4 and electron blocking layer 5 can be disposed between anode layer 2 and light-emitting layer 6.

[0068] The hole injection layer structure consists of a hole injection layer material uniformly or non-uniformly dispersed in the hole transport layer. The hole injection material can be, for example, a P-doped material. The P-doped material can be selected from at least one compound selected from the following: quinone derivatives, such as tetracyanoquinone dimethyl ethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl ethane (F4-TCNQ); metal oxides, such as tungsten oxide or molybdenum oxide; or cyano-containing compounds, such as compounds P1, NDP, and F4-TCNQ shown below:

[0069]

[0070] According to the present invention, P1 is preferably used as the P dopant. The ratio of hole transport layer to P dopant used in the present invention is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0071] The thickness of the hole injection layer of the present invention can be 1-100 nm, preferably 2-50 nm, and more preferably 5-20 nm.

[0072] The hole transport layer is preferably made of a material with high hole mobility, which enables holes to be transferred from the anode or hole injection layer to the light-emitting layer. Hole transport materials can be phthalocyanine derivatives, triazole derivatives, triarylmethane derivatives, triarylamine derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, stilbene derivatives, pyridinium derivatives, polysilane derivatives, imidazole derivatives, phenylenediamine derivatives, amino-substituted quinone derivatives, styrene-based anthracene derivatives, styrene-based amine derivatives, styrene compounds, fluorene derivatives, spirofluorene derivatives, silazane derivatives, aniline copolymers, porphyrin compounds, carbazole derivatives, polyaryl alkane derivatives, polyphenylene oxide and its derivatives, polythiophene and its derivatives, poly-N-vinylcarbazole derivatives, thiophene oligomers and other conductive polymers, aromatic tertiary amine compounds, and styrene aminations. Compounds, triamines, tetraamines, benzidines, propyne diamine derivatives, p-phenylenediamine derivatives, m-phenylenediamine derivatives, 1,1'-bis(4-diarylaminophenyl)cyclohexane, 4,4'-bis(diarylamine)biphenyls, bis[4-(diarylamino)phenyl]methanes, 4,4”-bis(diarylamino)terphenyls, 4,4”'-bis(diarylamino)tetraphenyls, 4,4'-bis(diarylamino)diphenyl ethers, 4,4'-bis(diarylamino)diphenylsulfanes, bis[4-(diarylamino)phenyl]dimethylmethanes, bis[4-(diarylamino)phenyl]-bis(trifluoromethyl)methanes, or 2,2-diphenylethylene compounds, etc.

[0073] The thickness of the hole transport layer of the present invention can be 5-200 nm, preferably 10-180 nm, and more preferably 20-150 nm.

[0074] The electron blocking layer requires that its triplet (T1) energy level be higher than that of the host material in the emissive layer, thus blocking energy loss from the emissive layer material. The HOMO energy level of the electron blocking layer material should be between that of the hole transport layer material and the host material of the emissive layer, facilitating hole injection from the positive electrode into the emissive layer. Simultaneously, the electron blocking layer material should possess high hole mobility to promote hole transport and reduce the power consumption of the device. The LUMO energy level of the electron blocking layer material should be higher than that of the host material of the emissive layer, serving as an electron blocker; that is, the electron blocking layer material should have a wide bandgap (Eg). Electron blocking layer materials meeting these conditions can be triarylamine derivatives, fluorene derivatives, spirofluorene derivatives, dibenzofuran derivatives, carbazole derivatives, etc. Preferred are triarylamine derivatives, such as N4,N4-bis([1,1′-biphenyl]-4-yl)-N4′-phenylN4′-[1,1′:4′,1″-terphenyl]-4-yl-[1,1′-biphenyl]-4,4′-diamine; spirofluorene derivatives, such as N-([1,1′-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-furan-2-yl)-9,9′-spirodifluorene-2-amine; dibenzofuran derivatives, such as N,N-bis([1,1′-biphenyl]-4-yl)-3′-(dibenzo[b,d]furan-4-yl)-[1,1′-biphenyl]-4-amine, but not limited thereto.

[0075] According to the present invention, the thickness of the electron blocking layer can be 1-200 nm, preferably 5-150 nm, and more preferably 10-100 nm.

[0076] According to the present invention, the light-emitting layer is located between the first electrode and the second electrode. The material of the light-emitting layer is a material that emits visible light by respectively receiving holes from the hole transport region and electrons from the electron transport region, and combining the received holes and electrons. The light-emitting layer may include a host material and a dopant material. As the host and guest materials of the light-emitting layer of the organic electroluminescent device of the present invention, the host material may be one or a combination of two of the following: anthracene derivatives, quinoxaline derivatives, triazine derivatives, xanthones, diphenyl ketone derivatives, carbazole derivatives, pyridine derivatives, or pyrimidine derivatives. The guest material may be a pyrene derivative, boron derivative, chrysodium derivative, spirofluorene derivative, iridium complex, or platinum complex.

[0077] A hole-blocking layer can be disposed above the emissive layer. The triplet (T1) energy level of the hole-blocking layer material is higher than the T1 energy level of the main emissive layer material, thus preventing energy loss from the emissive layer material. The HOMO energy level of the material is lower than the HOMO energy level of the main emissive layer material, also serving to block holes. Simultaneously, the hole-blocking layer material is required to have high electron mobility to facilitate electron transport and reduce the power consumption of the device. Hole-blocking layer materials meeting these conditions can be triazine derivatives, azirene derivatives, etc. Triazine derivatives are preferred, but not limited to these.

[0078] The thickness of the hole blocking layer of the present invention can be 2-200 nm, preferably 5-150 nm and more preferably 10-100 nm, but the thickness is not limited to this range.

[0079] An electron transport layer may be disposed above a hole blocking layer. The electron transport layer material is one that readily receives electrons from the cathode and transfers the received electrons to the light-emitting layer. The electron transport layer comprises one or more organic compounds of the present invention containing triazine and pyrimidine structures. Preferably, the electron transport layer consists of the organic compounds of the present invention and other electron transport layer materials. More preferably, the other electron transport layer materials are materials commonly known in the art. Most preferably, the electron transport layer consists of the organic compounds of the present invention containing triazine and pyrimidine structures and Liq.

[0080] The thickness of the electron transport layer of the present invention can be 10-80 nm, preferably 20-60 nm, and more preferably 25-45 nm.

[0081] In the electron transport layer of the organic electroluminescent device according to the present invention, the ratio of the organic compound containing triazine and pyrimidine structures and other electron transport layer materials is 1:9-9:1, preferably 2:8-8:2, more preferably 4:6-6:4, and most preferably 5:5.

[0082] As the electron transport compound of the present invention, one or more organic compounds containing triazine and pyrimidine structures are preferably used.

[0083] The electron injection layer material is preferably a metallic Yb with a low work function, which facilitates electron injection into the organic functional material layer. The thickness of the electron injection layer of the present invention can be 0.1-5 nm, preferably 0.5-3 nm, and more preferably 0.8-1.5 nm.

[0084] The second electrode can be a cathode, and the material used to form the cathode can be a material with low work function, such as metals, alloys, conductive compounds, or mixtures thereof. Non-limiting examples of cathode materials can include lithium (Li), ytterbium (Yb), magnesium (Mg), aluminum (Al), calcium (Ca), as well as aluminum-lithium (Al-Li), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). The thickness of the cathode depends on the material used, typically 5-100 nm, preferably 7-50 nm, and more preferably 10-25 nm.

[0085] Optionally, to improve the light extraction efficiency of the organic electroluminescent device, a light extraction layer (i.e., a CPL layer) can be added above the second electrode (i.e., the cathode) of the device. According to the principles of optical absorption and refraction, the CPL layer material should have a higher refractive index and a lower absorption coefficient. Any material known in the art can be used as the CPL layer material, such as Alq3. The thickness of the CPL layer is typically 5-300 nm, preferably 20-100 nm, and more preferably 40-80 nm.

[0086] Optionally, the organic electroluminescent device may also include an encapsulation structure. The encapsulation structure may be a protective structure preventing external substances such as moisture and oxygen from entering the organic layer of the organic electroluminescent device. The encapsulation structure may be, for example, a can, such as a glass or metal can; or a thin film covering the entire surface of the organic layer.

[0087] Methods for fabricating organic electroluminescent devices

[0088] The present invention also relates to a method for fabricating the above-mentioned organic electroluminescent device, comprising sequentially laminating a first electrode, a multilayer organic thin film layer, and a second electrode on a substrate. The multilayer organic thin film layer is formed by sequentially laminating a hole transport region, a light-emitting layer, and an electron transport region on the first electrode from bottom to top. The hole transport region is formed by sequentially laminating a hole injection layer, a hole transport layer, and an electron blocking layer on the first electrode from bottom to top, and the electron transport region is formed by sequentially laminating a hole blocking layer, an electron transport layer, and an electron injection layer on the light-emitting layer from bottom to top. Optionally, a CPL layer may also be laminated on the second electrode to improve the light extraction efficiency of the organic electroluminescent device.

[0089] Regarding lamination, methods such as vacuum deposition, vacuum evaporation, spin coating, casting, LB method, inkjet printing, laser printing, or LITI can be used, but are not limited to these. Among them, vacuum evaporation refers to heating the material and depositing it onto the substrate in a vacuum environment.

[0090] In this invention, vacuum evaporation is preferably used to form the various layers, wherein the vapor deposition process can be carried out at a temperature of about 100-500°C for about 10... -8 -10 -2 The vacuum degree and about Vacuum evaporation is performed at a rate of [missing information]. The vacuum level is preferably 10 [missing information]. -6 -10 -2 Torr, more preferably 10 -5 -10 -3 Torr. The rate is approximately More preferably, about

[0091] In addition, it should be noted that the materials used to form each layer described in this invention can be used as a single layer by forming a film on their own, or they can be used as a single layer by mixing with other materials to form a film. They can also be a stacked structure between layers that are formed on their own, a stacked structure between layers that are formed by mixing, or a stacked structure between layers that are formed on their own and layers that are formed by mixing.

[0092] Display elements

[0093] The present invention also relates to a display device including the aforementioned organic electroluminescent devices, particularly a flat panel display device. In a preferred embodiment, the display device may include one or more of the aforementioned organic electroluminescent devices, and in the case of multiple devices, the devices are stacked laterally or vertically. The display device may also include at least one thin-film transistor. The thin-film transistor may include a gate electrode, a source electrode and a drain electrode, a gate insulating layer and an active layer, wherein one of the source electrode and the drain electrode may be electrically connected to a first electrode of the organic electroluminescent device. The active layer may include crystalline silicon, amorphous silicon, organic semiconductor or oxide semiconductor, but is not limited thereto.

[0094] Example

[0095] I. Compound Preparation Examples

[0096] All raw materials involved in the synthesis embodiments of the present invention can be purchased from the market or obtained by conventional preparation methods in the art;

[0097] Preparation of intermediate C1:

[0098]

[0099] Under nitrogen protection, in a 500 mL round-bottom flask, raw material A1 (30 mmol), raw material B1 (33 mmol), KOAC (90 mmol), and dioxane (200 mL) were added sequentially. Nitrogen was purged for 30 min to replace the air. Pd(PPh3)4 (0.6 mmol) was then added, and the mixture was heated under reflux for 12 h under nitrogen protection. TCL analysis of the reaction solution showed that raw material A1 reacted completely. After the reaction was complete, the reaction system was naturally cooled to room temperature, poured into a separatory funnel, shaken, and allowed to separate into layers. The aqueous phase was extracted with dichloromethane (50 mL * 3). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated to remove dichloromethane, yielding intermediate C1. LC-MS: Measured value: 436.32 ([M+H) + ); Precision quality: 435.21.

[0100] Intermediate C was prepared using a synthetic method similar to that of intermediate C1. The raw materials A and B used are shown in Table 1.

[0101] Table 1

[0102]

[0103] Preparation of intermediates D1, E1, and F1:

[0104]

[0105] Under nitrogen protection, in a 500 mL round-bottom flask, raw material D1 (20 mmol) and diethyl ether (150 mL) were added sequentially. The mixture was cooled to -78 °C, and nitrogen was purged for 30 min to replace the air. A 1.6 mol / L hexane solution of n-butyllithium (15 mL, 25 mmol) was slowly added, and the reaction was maintained at -78 °C for 3 h. Then, trimethyl borate (2.8 mL, 25 mmol) was added, and the reaction was maintained at -78 °C for 1 h. The mixture was then allowed to react at room temperature for 18 h. TCL analysis of the reaction solution showed that raw material D1 had reacted completely. After the reaction was complete, a dilute hydrochloric acid solution (30 mL) was added to the reaction system, and the organic solvent was removed by rotary evaporation. The residue was filtered to obtain a white solid intermediate, D1. LC-MS: Measured value: 277.24 ([M+H)). + Precision mass: 276.11

[0106] Under nitrogen protection, in a 250 mL round-bottom flask, raw material E1 (20 mmol), intermediate D1 (22 mmol), K2CO3 (60 mmol), tetrahydrofuran (120 mL), and water (30 mL) were added sequentially. Nitrogen gas was purged for 30 min to replace the air. Pd(PPh3)4 (0.5 mmol) was added, and the mixture was heated under reflux for 11 h under nitrogen protection. TCL analysis of the reaction solution showed that raw material E1 reacted completely. After the reaction was complete, the reaction system was naturally cooled to room temperature, and the solvent was removed by rotary evaporation. The residue was dissolved in 120 mL of dichloromethane, washed with 80 mL of water, poured into a separatory funnel, shaken, and allowed to stand for separation. The aqueous phase was extracted with dichloromethane (40 mL * 3). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated to remove dichloromethane to obtain the crude product. The crude product was purified by silica gel column chromatography to obtain intermediate E1. LC-MS: Measured value: 421.12 ([M+H) + Precision weight: 420.00

[0107] Under nitrogen protection, intermediate E1 (10 mmol), starting material F1 (11 mmol), K2CO3 (30 mmol), tetrahydrofuran (120 mL), and water (30 mL) were added sequentially to a 250 mL round-bottom flask. Nitrogen gas was purged for 30 min to replace the air. Pd(PPh3)4 (0.2 mmol) was added, and the mixture was heated under reflux for 15 h under nitrogen protection. TCL analysis of the reaction solution showed that intermediate E1 reacted completely. After the reaction was complete, the reaction system was naturally cooled to room temperature, and the solvent was removed by rotary evaporation. The residue was dissolved in 100 mL of dichloromethane, washed with 50 mL of water, poured into a separatory funnel, shaken, and allowed to stand for separation. The aqueous phase was extracted with dichloromethane (30 mL * 3). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated to remove dichloromethane to obtain the crude product. The crude product was purified by silica gel column chromatography to obtain intermediate F1. LC-MS: Measured value: 469.25 ([M+H) + ); Precision quality: 468.14.

[0108] Intermediate D was prepared using a similar synthetic method to intermediate D1, and the raw material D1 used is shown in Table 2.

[0109] Intermediate E was prepared using a synthetic method similar to that of intermediate E1. The raw material E1 and intermediate D1 used are shown in Table 2.

[0110] Intermediate F was prepared using a synthetic method similar to that of intermediate F1. The intermediate E1 and raw material F1 used are shown in Table 2.

[0111] Table 2

[0112]

[0113]

[0114]

[0115] Intermediate F1: LC-MS: Measured value: 469.25 ([M+H]) + ); Precision quality: 468.14.

[0116] Intermediate F2: LC-MS: Measured value: 469.30 ([M+H]) + ); Precision quality: 468.14.

[0117] Intermediate F3: LC-MS: Measured value: 420.23 ([M+H]) + ); Precision quality: 419.12.

[0118] Intermediate F4: LC-MS: Measured value: 470.20 ([M+H]) + ); Precision quality: 469.13.

[0119] Intermediate F5: LC-MS: Measured value: 509.24 ([M+H]) + ); Precision quality: 508.13.

[0120] Intermediate F6: LC-MS: Measured value: 545.26 ([M+H]) + ); Precision quality: 544.17.

[0121] Intermediate F7: LC-MS: Measured value: 545.21 ([M+H]) + ); Precision quality: 544.17.

[0122] Intermediate F8: LC-MS: Measured value: 469.33 ([M+H]) + ); Precision quality: 468.14.

[0123] Intermediate F9: LC-MS: Measured value: 469.15 ([M+H]) + ); Precision quality: 468.14.

[0124] Intermediate F10: LC-MS: Measured value: 495.20 ([M+H]) + ); Precision quality: 494.15.

[0125] Intermediate F11: LC-MS: Measured value: 519.22 ([M+H]) + ); Precision quality: 518.15.

[0126] Intermediate F12: LC-MS: Measured value: 545.29 ([M+H]) +); Precision quality: 544.17.

[0127] Intermediate F13: LC-MS: Measured value: 545.35 ([M+H]) + ); Precision quality: 544.17.

[0128] Intermediate F14: LC-MS: Measured value: 459.33 ([M+H]+); Precise mass: 458.12.

[0129] Example 1: Synthesis of Compound 1

[0130]

[0131] Under nitrogen protection, intermediate F1 (20 mmol), intermediate C1 (22 mmol), K2CO3 (60 mmol), tetrahydrofuran (100 mL), and water (50 mL) were added sequentially to a 250 mL round-bottom flask. Nitrogen gas was purged for 30 min to replace the air. Palladium acetate (0.25 mmol) and 2-dicyclohexylphosphine-2′,4′,6′-triisopropylbiphenyl (0.45 mmol) were then added. The mixture was heated under nitrogen protection and refluxed for 15 h. TCL analysis of the reaction solution revealed that intermediate F1 reacted completely. After the reaction was complete, the reaction system was naturally cooled to room temperature, and the solvent was removed by rotary evaporation. The residue was dissolved in 200 ml of dichloromethane, washed with 150 ml of water, poured into a separatory funnel, shaken, and allowed to stand for phase separation. The aqueous phase was extracted with dichloromethane (80 ml * 3). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the filtrate was rotary evaporated to remove dichloromethane to obtain the crude product. The crude product was purified by silica gel column chromatography to obtain compound 1. Elemental analysis: C 53 H 35 N5; Theoretical values: C, 85.80; H, 4.76; N, 9.44; Measured values: C, 85.84; H, 4.70; N, 9.50. LC-MS: Measured value: 742.46 ([M+H]+), Precise mass: 741.29.

[0132] Example 2: Synthesis of Compound 2

[0133]

[0134] Compound 2 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F1 was replaced by intermediate F2. Elemental analysis: C 53 H35N5; Theoretical values: C, 85.80; H, 4.76; N, 9.44; Measured values: C, 85.86; H, 4.71; N, 9.48. LC-MS: Measured value: 742.26 ([M+H]+), Precise mass: 741.29.

[0135] Example 3: Synthesis of Compound 5

[0136]

[0137] Compound 5 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F1 was replaced with intermediate F3. Elemental analysis: C 48 H 32 N6; Theoretical values: C, 83.21; H, 4.66; N, 12.13; Measured values: C, 83.14; H, 4.69; N, 12.20. LC-MS: Measured value: 693.71 ([M+H]+), Precise mass: 692.27.

[0138] Example 4: Synthesis of Compound 6

[0139]

[0140] Compound 6 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F1 was replaced with intermediate F4. Elemental analysis: C 52 H 34 N6; Theoretical values: C, 84.07; H, 4.61; N, 11.31; Measured values: C, 84.02; H, 4.54; N, 11.37. LC-MS: Measured value: 743.63 ([M+H]+), Precise mass: 742.28.

[0141] Example 5: Synthesis of Compound 15

[0142]

[0143] Compound 15 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F1 was replaced by intermediate F5. Elemental analysis: C 55 H 35 N5O; Theoretical values: C, 84.49; H, 4.51; N, 8.96; Measured values: C, 84.44; H, 4.44; N, 8.99. LC-MS: Measured value: 782.51 ([M+H]+), Precise mass: 781.28.

[0144] Example 6: Synthesis of Compound 19

[0145]

[0146] Compound 19 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F1 was replaced by intermediate F6. Elemental analysis: C 59 H 39N5; Theoretical values: C, 86.63; H, 4.81; N, 8.56; Measured values: C, 86.64; H, 4.83; N, 8.47. LC-MS: Measured value: 818.28 ([M+H]+), Precise mass: 817.32.

[0147] Example 7: Synthesis of Compound 20

[0148]

[0149] Compound 20 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F7 was used instead of intermediate F1. Elemental analysis: C 59 H 39 N5; Theoretical values: C, 86.63; H, 4.81; N, 8.56; Measured values: C, 86.71; H, 4.76; N, 8.53. LC-MS: Measured value: 818.60 ([M+H]+), Precise mass: 817.32.

[0150] Example 8: Synthesis of Compound 40

[0151]

[0152] Compound 40 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F9 was used instead of intermediate F1. Elemental analysis: C 53 H 35 N5; Theoretical values: C, 85.80; H, 4.76; N, 9.44; Measured values: C, 85.75; H, 4.79; N, 9.49. LC-MS: Measured value: 742.38 ([M+H]+), Precise mass: 741.29.

[0153] Example 9: Synthesis of Compound 41

[0154]

[0155] Compound 41 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F1 was replaced with intermediate F8. Elemental analysis: C 53 H 35 N5; Theoretical values: C, 85.80; H, 4.76; N, 9.44; Measured values: C, 85.79; H, 4.73; N, 9.40. LC-MS: Measured value: 742.46 ([M+H]+), Precise mass: 741.29.

[0156] Example 10: Synthesis of Compound 47

[0157]

[0158] Compound 47 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F1 was replaced by intermediate F1 instead of intermediate F1. Elemental analysis: C 55 H 37 N5; Theoretical values: C, 86.02; H, 4.86; N, 9.12; Measured values: C, 85.99; H, 4.88; N, 9.15. LC-MS: Measured value: 768.58 ([M+H]+), Precise mass: 767.30.

[0159] Example 11: Synthesis of Compound 48

[0160]

[0161] Compound 48 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F1 was replaced by intermediate F1. Elemental analysis: C 57 H 37 N5; Theoretical values: C, 86.45; H, 4.71; N, 8.84; Measured values: C, 86.42; H, 4.75; N, 8.81. LC-MS: Measured value: 792.58 ([M+H]+), Precise mass: 791.30.

[0162] Example 12: Synthesis of Compound 54

[0163]

[0164] Compound 54 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F1 was replaced by intermediate F1 with intermediate F1. Elemental analysis: C 59 H 39 N5; Theoretical values: C, 86.63; H, 4.81; N, 8.56; Measured values: C, 86.65; H, 4.76; N, 8.62. LC-MS: Measured value: 818.60 ([M+H]+), Precise mass: 817.32.

[0165] Example 13: Synthesis of Compound 55

[0166]

[0167] Compound 55 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F1 was replaced by intermediate F1 with intermediate F1. Elemental analysis: C 59 H39N5; Theoretical values: C, 86.63; H, 4.81; N, 8.56; Measured values: C, 86.67; H, 4.84; N, 8.54. LC-MS: Measured value: 818.37 ([M+H]+), Precise mass: 817.32.

[0168] Example 14: Synthesis of Compound 60

[0169]

[0170] Compound 60 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F2 was used instead of intermediate F1, and intermediate C2 was used instead of intermediate C1. Elemental analysis: C 59 H 39 N5; Theoretical values: C, 86.63; H, 4.81; N, 8.56; Measured values: C, 86.52; H, 4.79; N, 8.63. LC-MS: Measured value: 818.49 ([M+H]+), Precise mass: 817.32.

[0171] Example 15: Synthesis of Compound 78

[0172]

[0173] Compound 78 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F8 was used instead of intermediate F1, and intermediate C2 was used instead of intermediate C1. Elemental analysis: C 59 H 39 N5; Theoretical values: C, 86.63; H, 4.81; N, 8.56; Measured values: C, 86.74; H, 4.77; N, 8.68. LC-MS: Measured value: 818.54 ([M+H]+), Precise mass: 817.32.

[0174] Example 16: Synthesis of Compound 82

[0175]

[0176] Compound 82 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F1 was replaced by intermediate F1, and intermediate C2 was replaced by intermediate C1. Elemental analysis: C 65 H 43 N5; Theoretical values: C, 87.32; H, 4.85; N, 7.83; Measured values: C, 87.23; H, 4.90; N, 7.79. LC-MS: Measured value: 894.81 ([M+H]+), Precise mass: 893.35.

[0177] Example 17: Synthesis of Compound 103

[0178]

[0179] Compound 103 was prepared according to the synthetic method of Compound 1 in Example 1, except that intermediate F2 was used instead of intermediate F1, and intermediate C3 was used instead of intermediate C1. Elemental analysis: C 59 H 39 N5; Theoretical values: C, 86.63; H, 4.81; N, 8.56; Measured values: C, 86.70; H, 4.79; N, 8.60. LC-MS: Measured value: 818.64 ([M+H]+), Precise mass: 817.32.

[0180] Example 18: Synthesis of Compound 146

[0181]

[0182] Compound 146 was prepared according to the synthetic method of Compound 1 in Example 1, except that intermediate F8 was used instead of intermediate F1, and intermediate C5 was used instead of intermediate C1. Elemental analysis: C 57 H37N5; Theoretical values: C, 86.45; H, 4.71; N, 8.84; Measured values: C, 86.52; H, 4.66; N, 8.78. LC-MS: Measured value: 792.44 ([M+H]+), Precise mass: 791.30.

[0183] Example 19: Synthesis of Compound 165

[0184]

[0185] Compound 165 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F1 was replaced by intermediate F1, and intermediate C4 was replaced by intermediate C1. Elemental analysis: C 55 H 35 N5O; Theoretical values: C, 84.49; H, 4.51; N, 8.96; Measured values: C, 84.56; H, 4.44; N, 9.01. LC-MS: Measured value: 782.44 ([M+H]+), Precise mass: 781.28.

[0186] Example 20: Synthesis of Compound 178

[0187]

[0188] Compound 178 was prepared using the same synthetic method as Compound 1 in Example 1, except that intermediate F2 was used instead of intermediate F1, and intermediate C4 was used instead of intermediate C1. Elemental analysis: C 57 H 37N5; Theoretical values: C, 86.45; H, 4.71; N, 8.84; Measured values: C, 86.54; H, 4.64; N, 8.82. LC-MS: Measured value: 792.31 ([M+H]+), Precise mass: 791.30.

[0189] II. Device Fabrication Examples

[0190] The following describes in detail the application effect of the compound synthesized according to the present invention as an electron transport layer in a device through device Examples 1-20 and device Comparative Examples 1-16. Compared with device Example 1, device Examples 1-20 and device Comparative Examples 1-16 have the same fabrication process, use the same substrate material and electrode material, and the film thickness of the electrode material is also kept consistent. The difference is that the electron transport material in the device has been changed.

[0191] The molecular structural formulas of the relevant materials are shown below:

[0192]

[0193]

[0194] The structures of compounds ET-1 to ET-10 are shown above. All of the above materials were commercially available.

[0195] Device Example 1

[0196] The specific preparation process is as follows:

[0197] like Figure 1As shown, the transparent substrate layer 1 is a transparent PI film, and the anode is ITO (15nm) / Ag (150nm) / ITO (15nm). The anode layer 2 is washed by sequentially performing alkaline washing, pure water washing, drying, and then ultraviolet-ozone washing to remove organic residues on the surface of the anode layer. After the above washing, a hole injection layer 3 of HT-1 and P-1 with a thickness of 10nm is deposited on the anode layer 2 using a vacuum evaporation apparatus, with a mass ratio of HT-1 to P-1 of 97:3. Then, a hole transport layer 4 of HT-1 with a thickness of 135nm is deposited. Subsequently, an electron blocking layer 5 of EB-1 with a thickness of 40nm is deposited. After the above electron blocking materials are deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated, which includes H1:H2 = 47:47 (H1 and H2 with a mass ratio of 47:47 as the host material), GD-1 as the dopant material, with a doping ratio of 6% by weight, and a film thickness of 40nm. Following the aforementioned light-emitting layer 6, compound 1 and Liq are vacuum-deposited at a mass ratio of 1:1, resulting in a film thickness of 35 nm. This layer serves as the electron transport layer 7. On the electron transport layer 7, a 1 nm thick Yb layer is fabricated using a vacuum evaporation apparatus; this layer serves as the electron injection layer 8. On the electron injection layer 8, a 13 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus, with a Mg:Ag mass ratio of 1:9; this layer serves as the cathode layer 9. Finally, a 65 nm thick CPL-1 layer is deposited on top of this layer as the light extraction layer 10.

[0198] Device Examples 2-20 and Comparative Examples 1-10 were prepared in a similar manner to Device Example 1, and all used transparent PI film as the substrate and ITO (15nm) / Ag (150nm) / ITO (15nm) as the anode. The difference was that the parameters in Table 3 below were used.

[0199] Table 3

[0200]

[0201]

[0202]

[0203] III. Device Testing Examples

[0204] The devices fabricated in Part II were tested, including their driving voltage and LT95 lifetime. The driving voltage was measured at 10 mA / cm², using a Fostec IVL testing system. LT95 refers to the time it takes for the device's brightness to decay to 95% of its initial brightness; LT80 refers to the time it takes for the device's brightness to decay to 80% of its initial brightness. The lifetime testing system was an EAS-62C OLED device lifetime tester from System Technology Inc., Japan. The test results are shown in Table 4 below.

[0205] Table 4

[0206]

[0207] As can be seen from the device test data in Table 4 above, compared with devices using ET-1, ET-2, ET-3, ET-4, ET-5, ET-6, ET-7, ET-8, ET-9 and ET-10, the devices prepared using the compound of this invention as the electron transport layer material have basically the same device efficiency, significantly reduced device voltage, and about 20% improved lifespan at room temperature. However, the lifespan at high temperature is improved by more than 100%, showing a significant improvement in high-temperature lifespan.

[0208] The comparative compounds ET-1, ET-2, ET-3, ET-4, ET-5, ET-6, ET-7, ET-8, ET-9 and ET-10 used in the comparative examples have structural formulas similar to those of the present invention, with only minor differences, such as changes in bridging groups, changes in group connection sites, and differences in already connected groups. However, the compounds of the present invention have achieved better technical performance as electron transport materials than the comparative compounds, especially with a significant improvement in their high-temperature lifetime.

[0209] The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. An organic compound containing triazine and pyrimidine, characterized in that, The structure of the organic compound is shown in general formula (1): General formula (1) In general formula (1), R1 is independently represented as one of naphthyl, pyridyl, quinolinyl, isoquinolinyl, biphenyl, phenanthryl, dibenzofuranyl, and benzofuranyl; R2 and R3 are independently represented as phenyl, naphthyl, or biphenyl; X1 and X2 are independent tables, either C or N, and X1 and X2 have exactly one representation as N.

2. The organic compound according to claim 1, characterized in that, The structure of the organic compound is shown in any one of general formulas (2-1) to (2-2): General formula (2-1); General formula (2-2) In general formulas (2-1) to (2-2), R1 can be independently represented as one of naphthyl, pyridyl, quinolinyl, isoquinolinyl, biphenyl, phenanthryl, dibenzofuranyl, or benzofuranyl. R2 and R3 are independently represented as phenyl, naphthyl, or biphenyl.

3. The organic compound according to claim 1, characterized in that, The structure of the organic compound is shown in any one of general formulas (3-1) to (3-4): General formula (3-1); General formula (3-2); General formula (3-3) General formula (3-4) In general formulas (3-1) to (3-4), R2 and R3 are independently represented as phenyl, naphthyl, or biphenyl.

4. The organic compound according to claim 3, characterized in that, R3 represents phenyl or biphenyl.

5. The organic compound according to claim 3, characterized in that, R2 represents phenyl or biphenyl.

6. The organic compound according to claim 1, characterized in that, R1 is represented by the following structure: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 ； R2 and R3 are each independently represented as shown in the following structure: 、 、 、 、 、 。 7. The organic compound according to claim 1, characterized in that, The organic compound has a specific structure that is any one of the following: 1； 2； 3； 4； 5； 6； 7； 8； 9； 10； 11； 12； 13； 14； 15； 16； 19； 20； 21； 22； 23； 24； 25； 26； 27； 28； 29； 30； 31； 32； 33； 34； 36； 37； 38； 39； 40； 41； 42； 43； 44； 45； 46； 47； 48； 49； 50； 51； 52； 54； 55； 56； 57； 58； 59； 60； 61； 62； 63； 64； 65； 66； 67； 68； 69； 70； 71； 72； 74； 75； 76； 77； 78； 79； 80； 81； 82； 83； 84； 85； 86； 87； 88； 89； 90； 91； 92； 93； 94； 95； 97； 98； 99； 100； 101； 102； 103； 104； 105； 106； 107； 108； 109； 110； 111； 112； 114； 115； 117； 118； 119； 120； 121； 122； 123； 124； 125； 126； 127； 128； 129； 130； 131； 132； 133； 134； 135； 136； 137； 138； 139； 140； 141； 142； 143； 144； 145； 146； 147； 148； 149； 150； 151； 152； 153； 154； 155； 156； 157； 158； 159； 160； 161； 162； 163； 164； 165； 167； 168； 169； 170； 171； 172； 173； 175； 176； 177； 178； 179； 180； 181； 182； 183； 184； 185； 186； 187； 188； 189； 190。 8. An organic electroluminescent device, comprising a first electrode and a second electrode, wherein a multilayer organic thin film layer is disposed between the first electrode and the second electrode, characterized in that, At least one organic thin film layer contains the organic compound as described in any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic thin film layer includes an electron transport layer, which contains the organic compound according to any one of claims 1 to 7.

10. A display element, characterized in that, The display element comprises the organic electroluminescent device as described in claim 8 or 9.

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