A compound containing triazine and carbazole structure and an organic electroluminescence device

Abstract

This invention discloses a compound containing triazine and carbazole structures and an organic electroluminescent device, belonging to the field of semiconductor technology. The structure of the compound of this invention is shown in general formula (1). When the compound of this invention is applied to the light-emitting layer of an OLED device, it can achieve high device efficiency, and at the same time, it can significantly reduce device voltage and extend device life.

Description

Technical Field

[0001] This invention relates to the field of semiconductor technology, and in particular to a compound containing triazine and carbazole structures and an organic electroluminescent device. Background Technology

[0002] Organic Light Emission Diodes (OLEDs) technology can be used to manufacture new display products. OLED devices have a sandwich-like structure, consisting of electrode material layers and organic functional materials sandwiched between them. These various functional materials are stacked together according to their intended use to form the OLED device. As a current-emitting device, when a voltage is applied to its two electrodes, and an electric field is used to act on 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] In organic electroluminescent devices, a hole transport region can exist between the anode and the emissive layer, and an electron transport region can exist between the emissive layer and the cathode. Holes from the anode can migrate to the emissive layer through the hole transport region, and electrons from the cathode can migrate to the emissive layer through the electron transport region. Holes and electrons recombine in the emissive layer to generate excitons.

[0004] The light-emitting layer is composed of a host material and a dopant material. The dopant material is dispersed in the host material. The host material is divided into single host and dual host materials. The single host is composed of a single compound, while the dual host is composed of N-type (electron-type) material and P-type (hole-type) material. The dopant material is divided into fluorescent material and phosphorescent material. Among them, the phosphorescent material mainly relies on the spin coupling effect of heavy metal atoms to achieve a direct transition from the triplet state to the ground state, which can theoretically achieve 100% internal quantum yield.

[0005] Nevertheless, improvements in device voltage, current efficiency, and lifetime remain for triplet-emitting phosphorescent OLEDs. The performance of the host material in the emitting layer typically has a significant impact on these key performance characteristics of organic electroluminescent devices. According to existing technologies, host materials, particularly N-type and bipolar host compounds, often contain triazine groups. When existing triazine derivatives are used as host materials, improvements in device voltage, current efficiency, and device lifetime are required. Summary of the Invention

[0006] To address the aforementioned problems in the existing technology, this invention provides a compound containing triazine and carbazole structures. This invention provides a compound that, when used as the main material for the light-emitting layer of an organic electroluminescent device, can significantly reduce voltage, improve device efficiency, and especially greatly extend device lifespan.

[0007] The technical solution of the present invention is: a compound containing triazine and carbazole structures, the structure of which is shown in general formula (1):

[0008]

[0009] In general formula (1), X, X0, X1, X2, X3, X4, X5, X6, X7, and X8 represent CH, CD, C-Ph, C atoms, or N atoms;

[0010] Y represents either an O atom or an S atom;

[0011] R represents a hydrogen atom or C6-C. 30 aryl;

[0012] Ar represents phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl or carbazoleyl;

[0013] A represents phenyl, benzofuranyl, benzothiophenyl, or N-phenylindolyl;

[0014] m represents 0 or 1;

[0015] When m is 0, X5, X6, X7, and X8 are represented as CH;

[0016] When R represents a hydrogen atom, m represents 1, and Ar can only represent a carbazoyl group;

[0017] All H atoms in general formula (1) can be independently replaced by deuterium.

[0018] In a preferred embodiment, R represents phenyl, diphenyl, or triphenyl.

[0019] In a preferred embodiment, the structure of the compound is shown in general formula 1-1:

[0020]

[0021] In general formula 1-1, X, X0, X1, X2, X3, X4, X5, X6, X7, and X8 represent CH, CD, C-Ph, C atoms, or N atoms; Z1, Z2, Z3, Z4, and Z5 represent CH or C-Ph.

[0022] Y represents either O or S;

[0023] Ar represents phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl or carbazoleyl;

[0024] A represents phenyl, benzofuranyl, benzothiophenyl, or N-phenylindolyl;

[0025] m represents 0 or 1;

[0026] When m is represented as 0, X5, X6, X7, and X8 are represented as CH;

[0027] In general formula 1-1, all H atoms can be independently replaced by deuterium.

[0028] In a preferred embodiment, the structure of the compound is shown in general formulas 1-2:

[0029]

[0030] In general formulas 1-2, Z1, Z2, Z3, Z4, and Z5 represent CH or C-Ph;

[0031] Y represents an O or S atom;

[0032] Ar represents phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl or carbazoleyl;

[0033] A represents phenyl, benzofuranyl, benzothiophenyl, or N-phenylindolyl;

[0034] m represents 0 or 1;

[0035] In general formulas 1-2, all H atoms can be independently replaced by deuterium.

[0036] In a preferred embodiment, the structure of the compound is shown in general formulas 1-3:

[0037]

[0038] In general formulas 1-3, Z1, Z2, Z3, Z4, and Z5 represent CH or C-Ph;

[0039] Y represents an O or S atom;

[0040] Ar represents phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl or carbazoleyl;

[0041] A represents phenyl, benzofuranyl, benzothiophenyl, or N-phenylindolyl;

[0042] m represents 0 or 1;

[0043] All H atoms in general formulas 1-3 can be independently replaced by deuterium.

[0044] In a preferred embodiment, the structure of the compound is shown in general formulas 1-4 or 1-5:

[0045]

[0046] In general formulas 1-4 and 1-5, X, X0, X2, X3, X4, X5, X6, X7, and X8 represent CH, CD, C-Ph, C atoms, or N atoms;

[0047] Y represents either an O atom or an S atom;

[0048] R represents a hydrogen atom or C6-C. 30 aryl;

[0049] Ar represents phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, pyridyl or carbazoleyl;

[0050] A represents phenyl, benzofuranyl, benzothiophenyl, or N-phenylindolyl;

[0051] When R represents a hydrogen atom, Ar can only be represented as a carbazoyl group;

[0052] In general formulas 1-4 and 1-5, all H atoms can be independently replaced by deuterium.

[0053] In a preferred embodiment, the structure of the compound is shown in any one of general formulas 2-1 to 2-3:

[0054]

[0055] In general formulas 2-1 to 2-3, the definitions of Ar, A, Z1, Z2, Z3, Z4, Z5, and Y are the same as those defined above; The site that connects to the triazine is position 1, 2, 3, or 4;

[0056] The H atoms in general formulas 2-1 to 2-3 can all be independently replaced by deuterium.

[0057] In a preferred embodiment, the structure of the compound is shown in any one of general formulas 3-1 to 3-9:

[0058]

[0059] In general formulas 3-1 to 3-9, the definitions of Ar, A, Z1, Z2, Z3, Z4, Z5, and Y are the same as those defined above; The site that connects to the triazine is position 1, 2, 3, or 4;

[0060] The H atoms in formulas 3-1 to 3-9 can all be independently replaced by deuterium.

[0061] In a preferred embodiment, all or part of the hydrogen atoms in the compounds represented by formulas 3-1 to 3-8 are replaced by deuterium. In a preferred embodiment, the structure of the compound is represented as in any one of formulas 4-1 to 4-8.

[0062]

[0063]

[0064] In general formulas 4-1 to 4-8, Y represents an S or O atom.

[0065] In a preferred embodiment, the structure of the compound is shown in any one of general formulas 5-1 to 5-2:

[0066]

[0067] In general formulas 5-1 to 5-2, the definitions of Ar, A, Z1, Z2, Z3, Z4, Z5, and Y are the same as those defined above; The site that connects to the triazine is position 1, 2, 3, or 4;

[0068] The H atoms in formulas 5-1 to 5-2 can all be independently replaced by deuterium.

[0069] In a preferred embodiment, the structure of the compound is shown in any one of general formulas 6-1 to 6-9:

[0070]

[0071] In general formulas 6-1 to 6-9, the definitions of Ar, Z1, Z2, Z3, Z4, Z5, and Y are the same as those defined above;

[0072] The site that connects to the triazine is position 1, 2, 3, or 4;

[0073] The H atoms in formulas 6-1 to 6-9 can all be independently replaced by deuterium.

[0074] In a preferred embodiment, the structure of the compound is shown in any one of general formulas 7-1 to 7-3:

[0075]

[0076] In general formulas 7-1 to 7-3, the definitions of Ar, Z1, Z2, Z3, Z4, Z5, and Y are the same as those defined above;

[0077] The site that connects to the triazine is position 1, 2, 3, or 4;

[0078] The H atoms in formulas 7-1 to 7-3 can all be independently replaced by deuterium.

[0079] In a preferred embodiment, the structure of the compound is shown in general formulas 9-1 to 9-8:

[0080]

[0081] In general formulas 9-1 to 9-8, the definitions of Ar, A, Y, Z1, Z2, Z3, Z4, and Z5 are the same as those defined above.

[0082] The H atoms in formulas 9-1 to 9-8 can all be independently replaced by deuterium.

[0083] In a preferred embodiment, Ar is represented as Any one of them. In the preferred embodiment, A is represented as... Any one of them.

[0084] In a preferred embodiment, R represents a hydrogen atom, phenyl, naphthyl, diphenyl, or triphenyl.

[0085] In a preferred embodiment, R represents a hydrogen atom, Any one of the following. Preferably, the compound has a specific structure of any one of the following:

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092] An organic electroluminescent device includes a cathode, an anode, and a functional layer, wherein the functional layer is located between the cathode and the anode, and at least one functional layer contains the aforementioned compound containing triazine and carbazole structures.

[0093] In a preferred embodiment, the functional layer includes a light-emitting layer containing the aforementioned compound containing triazine and carbazole structures.

[0094] In a preferred embodiment, the light-emitting layer comprises a host material and a dopant material, wherein the host material contains the compound containing triazine and carbazole structures.

[0095] In a preferred embodiment, the main material of the light-emitting layer is formed by mixing the compound containing triazine and carbazole structures with any one or more of compounds GH-1 to GH-170, the specific structures of which are as follows:

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102] Compared with the prior art, the beneficial technical effects of the present invention are as follows:

[0103] 1) This invention achieves significant performance improvements by connecting donors with specific carbazole structures to triazine acceptors via bridging groups or direct connection, and by introducing dibenzofuran substituents (or dibenzothiophene substituents) onto the triazine groups. Materials with these structural features, when applied to the light-emitting layer of devices, can significantly reduce voltage, improve device efficiency, and substantially extend device lifetime, providing new alternative materials for electron-type hosts. Furthermore, by combining these materials with different hole-type materials, it has been found that they can achieve lower voltage, higher efficiency, and significantly extended device lifetime when paired with various hole-type materials.

[0104] 2) The compounds provided by this invention, by introducing deuterium atoms, help to further improve the device lifetime when applied to the light-emitting layer. Attached Figure Description

[0105] Figure 1 This is a schematic diagram of the structure of an OLED device (Top device) in which the materials listed in this invention are applied;

[0106] Wherein, 1 is a transparent substrate layer, 2 is an anode layer, 3 is a hole injection layer, 4 is a hole transport layer, 5 is an electron blocking layer, 6 is a light-emitting layer, 7 is a hole blocking layer, 8 is an electron transport layer, 9 is an electron injection layer, 10 is a cathode layer, and 11 is a CPL layer.

[0107] Figure 2 The NMR spectrum of compound 26;

[0108] Figure 3 The NMR spectrum of compound 61;

[0109] Figure 4 The NMR spectrum of compound 62;

[0110] Figure 5 The NMR spectrum of compound 63;

[0111] Figure 6 The NMR spectrum of compound 69;

[0112] Figure 7The NMR spectrum of compound 70;

[0113] Figure 8 The NMR spectrum of compound 71;

[0114] Figure 9 The NMR spectrum of compound 72;

[0115] Figure 10 The NMR spectrum of compound 179;

[0116] Figure 11 This is the NMR spectrum of compound 164. Detailed Implementation

[0117] The principles and features of the present invention are described below with reference to the accompanying drawings and embodiments. The examples given are only for explaining the present invention and are not intended to limit the scope of the present invention.

[0118] 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.

[0119] In this invention, the terms "upper," "lower," "top," and "bottom," used to describe electrodes, organic electroluminescent devices, and other structures, indicate orientation only in a specific state and do not imply that the structure can only exist in that orientation. Conversely, if the structure can be repositioned, such as by inverting it, the orientation of the structure changes accordingly. Specifically, in this invention, the "bottom" or "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 "top" or "upper" side.

[0120] 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.

[0121] An anode is formed on a substrate. The anode can be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode. When the anode is a transmissive electrode, it can be formed using a transparent metal oxide, such as indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), or indium tin zinc oxide (ITZO). When the anode is a semi-transmissive or reflective electrode, it can include Ag, Mg, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, or a mixture of metals. The thickness of the anode layer depends on the material used, typically 50-500 nm, preferably 70-300 nm, and more preferably 100-200 nm.

[0122] The organic functional material layer disposed between the anode and cathode can be sequentially composed of a hole transport region, a light-emitting layer, and an electron transport region from bottom to top.

[0123] The hole transport region that constitutes an organic electroluminescent device can be categorized as a hole injection layer, a hole transport layer, an electron blocking layer, etc.

[0124] As for the materials used in the hole injection layer, hole transport layer, and electron blocking layer, any material can be selected from known materials used in OLED devices.

[0125] Examples of the aforementioned materials include 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.

[0126] Furthermore, depending on the device configuration requirements, the hole transport film layer between the hole transport auxiliary layer and the hole injection layer of the organic electroluminescent device can be a single film layer or a stacked structure of multiple hole transport materials. In this paper, the film thickness of the various hole carrier conduction films with different functions is not particularly limited.

[0127] The hole injection layer comprises a host organic material capable of conducting holes, and a p-type doped material with a deep HOMO level (correspondingly, a deep LUMO level). Based on empirical observations, to achieve smooth hole injection from the anode to the organic film, the HOMO level of the host organic material used in the anode interface buffer layer must possess certain characteristics with the p-doped material. This is necessary to enable charge transfer states between the host and doped materials, achieve ohmic contact between the buffer layer and the anode, and realize efficient hole injection conduction from the electrode to the hole injection layer.

[0128] Based on the above empirical summary, different P-doped materials need to be selected to match the hole-based host materials of different HOMO energy levels in order to achieve ohmic contact at the interface and improve the hole injection effect.

[0129] Therefore, in one embodiment of the present invention, in order to improve hole injection, the hole injection layer further comprises a p-type dopant material selected from the following charge-conducting materials: quinone derivatives, such as tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethyl (F4-TCNQ); or hexaazatriphenyl derivatives, such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenyl (HAT-CN); or cyclopropane derivatives, such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-trimethylenetris(cyanoformyl))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides, such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0130] In the hole injection layer of the present invention, the ratio of hole transport material to P-type doped material is 99:1-95:5, preferably 99:1-97:3, based on mass meter.

[0131] The thickness of the hole injection layer of the present invention can be 5-100 nm, preferably 5-50 nm and more preferably 5-20 nm, but the thickness is not limited to this range.

[0132] The thickness of the hole transport layer of the present invention can be 5-200 nm, preferably 10-150 nm and more preferably 20-130 nm, but the thickness is not limited to this range.

[0133] The thickness of the electron blocking layer of the present invention can be 1-50 nm, preferably 5-40 nm, but the thickness is not limited to this range.

[0134] After forming the hole injection layer, hole transport layer, and electron blocking layer, a corresponding light-emitting layer is formed on top of the electron blocking layer.

[0135] The light-emitting layer may comprise a host material and a dopant material. The host material may be a compound containing triazine and carbazole structures as shown in the general formula (1) of this invention, and the dopant material may be a phosphorescent material conventional in the art.

[0136] In the light-emitting layer of the present invention, the ratio of the host material to the dopant material is 99:1-70:30, preferably 99:1-85:15 and more preferably 97:3-87:13, based on mass.

[0137] The thickness of the light-emitting layer can be adjusted to optimize luminous efficiency and driving voltage. The preferred thickness range is 5 nm to 50 nm, more preferably 10-50 nm, but the thickness is not limited to this range.

[0138] In this invention, the electron transport region may include, from bottom to top, a hole blocking layer, an electron transport layer, and an electron injection layer disposed on the light-emitting layer, but is not limited thereto.

[0139] A hole-blocking layer is a layer that prevents holes injected from the anode from passing through the light-emitting layer and entering the cathode, thereby extending the device's lifetime and improving its efficiency. The hole-blocking layer of this invention can be disposed on top of the light-emitting layer. As the hole-blocking layer material of the organic electroluminescent device of this invention, compounds with hole-blocking properties known in the prior art can be used, such as oxazole derivatives, triazole derivatives, triazine derivatives, pyrimidine derivatives, etc. The thickness of the hole-blocking layer of this invention can be 2-200 nm, preferably 5-150 nm, and more preferably 5-100 nm, but the thickness is not limited to this range.

[0140] An electron transport layer may be disposed above the light-emitting layer or (if present) a hole-blocking layer. The electron transport layer material is one that readily receives electrons from the cathode and transfers them to the light-emitting layer. Materials with high electron mobility are preferred. As the electron transport layer of the organic electroluminescent device of the present invention, electron transport layer materials known in the art for organic electroluminescent devices can be used, such as metal complexes of hydroxyquinoline derivatives represented by Alq3, BAlq, and Liq, various rare earth metal complexes, triazole derivatives, triazine derivatives, quinoxaline derivatives, phenanthroline derivatives, silicon-based compound derivatives, etc. 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, but the thickness is not limited to this range.

[0141] An electron injection layer may be disposed above the electron transport layer. The electron injection layer material is typically preferably a material with a low work function, allowing electrons to be easily injected into the organic functional material layer. As the electron injection layer material for the organic electroluminescent device of the present invention, electron injection layer materials known in the art for organic electroluminescent devices can be used, such as lithium; lithium salts, such as lithium 8-hydroxyquinoline, lithium fluoride, lithium carbonate, or lithium azide; or cesium salts, such as cesium fluoride, cesium carbonate, or cesium azide. The thickness of the electron injection layer of the present invention may be 0.1-5 nm, preferably 0.5-3 nm, and more preferably 0.8-1.5 nm, but the thickness is not limited to this range.

[0142] The cathode can be disposed above the electron transport region. The cathode can be a transmission electrode, a semi-transmission electrode, or a reflection electrode. When the cathode is a transmission electrode, it can include, for example, Li, Yb, Ca, LiF / Ca, LiF / Al, Al, Mg, BaF, Ba, Ag, or their compounds or mixtures; when the cathode is a semi-transmission electrode or a reflection electrode, it can include Ag, Mg, Yb, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, or their compounds or mixtures, but is not limited thereto. The thickness of the cathode depends on the material used, typically 10-50 nm, preferably 15-20 nm.

[0143] To improve the light extraction efficiency of organic electroluminescent devices, a light extraction layer (i.e., CPL layer, also known as a capping layer) can be added to the cathode of the device. Any material known in the art can be used as the CPL layer material. The thickness of the CPL capping layer is typically 5-300 nm, preferably 20-100 nm, and more preferably 40-80 nm.

[0144] The organic electroluminescent device of the present invention may further 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.

[0145] The method for preparing the organic electroluminescent device of the present invention includes sequentially laminating an anode, a hole injection layer, a hole transport layer, an electron blocking layer, an organic film layer, an electron transport layer, an electron injection layer, and a cathode, and optionally a capping layer, onto a substrate. In this regard, 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 thereto. In the present invention, vacuum evaporation is preferably used to form the various layers. Those skilled in the art can conventionally select the various process conditions in the vacuum evaporation method according to actual needs.

[0146] The raw materials and intermediates involved in the synthesis embodiments of the present invention can all be purchased from the market or prepared by conventional preparation methods in the art;

[0147] Synthesis of intermediate-2B

[0148]

[0149] Add starter-4b (11 mmol) to a flask, followed by starter-2d (11 mmol), cesium carbonate (50.0 mmol), and DMF (50 mL). Then, purge with nitrogen and stir at 120 °C for 16 h under nitrogen protection. After the reaction is complete, cool to room temperature, dilute the reaction mixture with ethyl acetate, and wash three times with saturated brine. Dry the mixture on anhydrous sodium sulfate, concentrate, and separate by silica gel column chromatography to obtain starter-1a.

[0150]

[0151] Add starting material -1a (80.0 mmol) to a flask, followed by pinacol diboronate (85.0 mmol), KOAc aqueous solution (250 mmol), DMF (250 mL), and PdCl2 (dppf) (2.0 mmol). Stir at 90 °C for 48 hours under nitrogen protection. After the reaction is complete and cooled to room temperature, the reaction liquid is diluted with ethyl acetate, followed by washing the organic phase with saturated brine. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue obtained after concentration is slurryed to obtain crude intermediate -2B. The crude product is then separated by silica gel column chromatography to obtain intermediate -2B. LC-MS: Theoretical value: 445.22; Measured value: 446.35 ([M+H)). + ).

[0152] Synthesis of intermediate-9B

[0153]

[0154] Add reactant-2a (13.0 mmol) to a flask, followed by reactant-2b (13.0 mmol), K₂CO₃ (50 mmol) aqueous solution, dioxane (50 mL), and Pd(PPh₃)₄ (0.2 mmol). The mixture was stirred under reflux for 16 hours under nitrogen protection. After the reaction was complete and cooled to room temperature, the reaction liquid was diluted with ethyl acetate (200 mL), followed by washing the organic phase with saturated brine. The organic phase was dried over anhydrous sodium sulfate and concentrated. The residue obtained from the concentrated organic phase was separated by silica gel column chromatography to obtain reactant-2c.

[0155] Add starting material -2c (11 mmol) to a flask, followed by starting material -2d (11 mmol), cesium carbonate (50.0 mmol), and DMF (50 mL). Then, purge with nitrogen and stir at 120 °C for 16 h under nitrogen protection. After the reaction is complete, cool to room temperature, dilute the reaction mixture with ethyl acetate, and wash three times with saturated brine. Dry the mixture on anhydrous sodium sulfate, concentrate, and separate by silica gel column chromatography to obtain starting material -2e.

[0156] The following reagents were added sequentially to the flask: starting material -2e (10.0 mmol), PdCl2 (dppf) (0.05 mmol), KOAc (30 mmol), and pinacol diboronate (11.0 mmol); followed by the addition of DMF (50 mL), purging with nitrogen, and stirring at 90 °C for 36 hours. After the reaction was complete and cooled to room temperature, the reaction liquid was diluted with ethyl acetate, washed three times with saturated brine, dried over anhydrous sodium sulfate, concentrated, and separated by silica gel column chromatography to obtain intermediate -9B; LC-MS: theoretical value: 521.25; determined value: 522.43 ([M+H)). + ).

[0157] Intermediate-18B

[0158]

[0159] Add reactant-3a (8.0 mmol), Pd(PPh3)4 (0.2 mmol), potassium carbonate (30 mmol) aqueous solution, and reactant-3b (8.0 mmol) sequentially to the flask, followed by dioxane (40 mL). Replace with nitrogen gas and reflux under nitrogen with stirring for 36 hours. After the reaction is complete, cool to room temperature, dilute the reaction liquid with ethyl acetate, wash with saturated brine, dry the organic phase with anhydrous sodium sulfate, concentrate, and separate by silica gel column chromatography to obtain intermediate-18B; LC-MS: theoretical value: 541.20; determined value: 542.18 ([M+H)). + ).

[0160] Intermediate-19B

[0161]

[0162] Add reactant-4a (10.0 mmol), Cs₂CO₃ (50 mmol), reactant-4b (10.0 mmol), and DMF (50 mL) sequentially to a flask. Stir at 120 °C for 24 hours under nitrogen protection. After the reaction is complete, cool to room temperature, dilute the reaction liquid with ethyl acetate, wash three times with saturated brine, dry the organic phase with anhydrous sodium sulfate, concentrate, and separate by silica gel column chromatography to obtain reactant-4c.

[0163] Add the following to the flask sequentially: starting material -4c (7.0 mmol), potassium acetate (20 mmol), pinacol diboronate (8.0 mmol), PdCl2 (dppf) (0.20 mmol), and DMF (30 mL). Stir at 90 °C for 24 hours under nitrogen protection. After the reaction is complete, cool to room temperature, dilute the reaction liquid with ethyl acetate, wash three times with saturated brine, dry the organic phase with anhydrous sodium sulfate, concentrate, and separate by silica gel column chromatography to obtain intermediate -19B; LC-MS: theoretical value: 610.28; determined value: 611.35 ([M+H)). + ).

[0164] Intermediate-20B

[0165]

[0166] The preparation of intermediate-20B is based on the synthesis process of intermediate-19B, except that raw material-5a is used instead of raw material-4a.

[0167] Intermediate-20B; LC-MS: Theoretical value: 453.27; Measured value: 454.41 ([M+H]) + ).

[0168] Intermediate-25A:

[0169]

[0170] Add reactants -6a (20.0 mmol), -6b (25.0 mmol), K₂CO₃ (100 mmol) aqueous solution, toluene (80 mL), and Pd(PPh₃)₄ (0.5 mmol) sequentially to the addition flask; reflux and stir for 16 hours under nitrogen protection. After the reaction is complete and cooled to room temperature, dilute with ethyl acetate, wash with brine, dry with anhydrous sodium sulfate, concentrate the organic phase, and separate the residue by silica gel column chromatography to give intermediate -25A; LC-MS: theoretical value: 446.09; determined value: 447.31 ([M+H)₂) + ).

[0171] Synthesis of intermediate-26B:

[0172]

[0173] Add reactant-2a (50 mmol), reactant-26a (50 mmol), dioxane (500 mL), water (100 mL), potassium carbonate (150 mmol), and Pd(PPh3)4 (2 mmol) sequentially to the flask; reflux for 6 hours under nitrogen protection. After the reaction is complete and cooled to room temperature, add saturated brine, extract three times with ethyl acetate, then dry with anhydrous sodium sulfate, filter and concentrate the organic phase, and purify the residue by silica gel column chromatography to obtain compound reactant-26b;

[0174] Add reactant-26b (20 mmol), reactant-2d (20 mmol), DMF (200 ml), and cesium carbonate (150 mmol) sequentially to a flask. Stir at 120 °C for 6 hours under nitrogen protection. After the reaction is complete and cooled to room temperature, dilute the reaction solution with ethyl acetate, filter, wash away DMF with saturated brine, concentrate the organic phase, add petroleum ether to precipitate, and filter to obtain reactant-26c.

[0175] The following ingredients were added sequentially to a flask: starting material -26C (18 mmol), pinacol diboronate (20.0 mmol), Pd(dppf)Cl2 (0.5 mmol), potassium acetate (50 mmol), and dioxane (150 mL). Under nitrogen protection, the mixture was stirred at 80 °C for 16 h. After the reaction was complete, the temperature was lowered, saturated brine was added, and the mixture was extracted with ethyl acetate. The organic phase was filtered through diatomaceous earth, concentrated, filtered, and slurryed to obtain intermediate -26B. LC-MS: Theoretical value: 450.25; Measured value: 451.39 ([M+H)). + ).

[0176] Example 1: Synthesis of Compound 1:

[0177]

[0178] Intermediate-1A (10.0 mmol) was added to a flask, followed by intermediate-1B (10.5 mmol), K₂CO₃ (50.0 mmol) aqueous solution, toluene (50 mL), ethanol (20 mL), and Pd(PPh₃)₄ (0.2 mmol). The mixture was refluxed under nitrogen protection for 36 hours. After the reaction was completed and cooled to room temperature, saturated brine was added, and the mixture was extracted three times with ethyl acetate. The extract was then dried over anhydrous sodium sulfate, filtered, and the organic phase was concentrated. The residue was purified by silica gel column chromatography to give compound 1.

[0179] Preparation of the synthetic reference compound-1 in Examples 2 to 26; the difference being that intermediate-1A was replaced by starting material / intermediate A and intermediate-1B was replaced by starting material / intermediate B.

[0180] Table 1

[0181]

[0182]

[0183]

[0184]

[0185]

[0186] For details of the NMR spectrum of compound 26, please refer to [link to NMR spectrum]. Figure 2 :

[0187] 1 H NMR(400MHz,Chloroform-d)δ9.0-8.98(m,1H),8.94-8.92(m,3H),8.77-8.74(m,2H),8.13-8.11(m,2H),8.05-7.97(m, 4H),7.87-7.85(m,1H),7.60-7.58(m,2H),7.52-7.48(m,2H),7.38-7.31(m,4H),7.26-7.17(m,4H),7.09-6.99(m,5H).

[0188] For details of the NMR spectrum of compound 61, please refer to [link to NMR spectrum]. Figure 3 :

[0189] 1 H NMR (400MHz, Chloroform-d) δ9.05-8.85(m,6H),8.16-8.14(m,8H),7.68-7.53(m,6H),7.44-7.30(m,3H),7.23-7.13(m,6H),7.05-7.03(m,3H).

[0190] For details of the NMR spectrum of compound 62, please refer to [link to NMR spectrum]. Figure 4 :

[0191] 1 H NMR (400MHz, Chloroform-d) δ9.02-8.81(m,6H),8.13-7.81(m,9H),7.66-7.52(m,5H),7.43-7.30(m,3H),7.26-7.18(m,4H),7.12-7.02(m,5H).

[0192] For details of the NMR spectrum of compound 63, please refer to [link to NMR spectrum]. Figure 5 :

[0193] 1H NMR (400MHz, Chloroform-d) δ9.13-8.81(m,6H),8.10-7.92(m,7H),7.74-7.50(m,7H),7.40-7.31(m,3H),7.25-7.15(m,6H),7.05-7.03(m,3H).

[0194] For details of the NMR spectrum of compound 69, please refer to [link to NMR spectrum]. Figure 6 :

[0195] 1 H NMR (400MHz, Chloroform-d) δ8.97-8.34(m,6H),8.09-7.84(m,7H),7.71-7.52(m,7H),7.34-7.13(m,9H),7.05-7.04(m,3H).

[0196] For details of the NMR spectrum of compound 70, please refer to [link to NMR spectrum]. Figure 7 :

[0197] 1 H NMR (400MHz, Chloroform-d) δ8.93-8.85(m,4H),8.65-8.43(m,2H),8.13-7.84(m,8H),7.71-7.53(m,6H),7.37-7.21(m,7H),7.15-7.05(m,5H).

[0198] For details of the NMR spectrum of compound 71, please refer to [link to NMR spectrum]. Figure 8 :

[0199] 1 H NMR (400MHz, Chloroform-d) δ8.98-8.85(m,4H),8.66-8.43(m,2H),8.09-7.84(m,7H),7.71-7.52(m,7H),7.34-7.13(m,9H),7.05-7.04(m,3H).

[0200] For details of the NMR spectrum of compound 72, please refer to [link to NMR spectrum]. Figure 9 :

[0201] 1 H NMR (400MHz, Chloroform-d) δ9.11-8.39(m,6H),8.12-7.77(m,7H),7.67-7.54(m,6H),7.33-7.00(m,13H).

[0202] For details of the NMR spectrum of compound 179, please refer to [link to NMR spectrum]. Figure 10 :

[0203] 1 H NMR (400MHz, Chloroform-d) δ9.09-8.63(m,6H),8.14-7.86(m,7H),7.57-7.33(m,9H),7.28-7.21(m,4H),7.13-7.04(m,5H).

[0204] For details of the NMR spectrum of compound 164, please refer to [link to NMR spectrum]. Figure 11 :

[0205] 1 H NMR (400MHz, Chloroform-d) δ9.06-8.78(m,6H),8.17-7.92(m,5H),7.65-7.53(m,5H),7.43-7.35(m,3H),7.30-7.21(m,4H).

[0206] Device Example 1

[0207] like Figure 1 As shown, the transparent substrate layer 1 is a transparent PI film. The anode layer 2 (ITO (15nm) / Ag (150nm) / ITO (15nm)) is washed sequentially with a cleaning agent (SemiClean M-L20), pure water, and dried, followed by ultraviolet-ozone washing to remove organic residues from the anode layer surface. After the above washing, HT-1 and P-1 are deposited as a hole injection layer 3 using a vacuum evaporation apparatus, with a film thickness of 10nm and a mass ratio of HT-1 to P-1 of 97:3. Next, HT-1 is deposited as a hole transport layer 4 with a thickness of 130nm. Subsequently, EB-1 is deposited as an electron blocking layer 5 with a thickness of 40nm. After the electron blocking layer material is deposited, the light-emitting layer 6 of the OLED light-emitting device is fabricated. Its structure includes compound-1 and GH-2 as the main materials, and GD-1 as the dopant material, with a doping ratio of 6% (mass ratio). The thickness of the light-emitting layer is 40 nm. Following the light-emitting layer 6, HB-1 is vacuum-deposited to a thickness of 5 nm; this layer is the hole blocking layer 7. Following the hole blocking layer 7, ET-1 and Liq are vacuum-deposited at a mass ratio of 1:1, resulting in a thickness of 35 nm; this layer is the electron transport layer 8. On the electron transport layer 8, a 1 nm thick LiF layer is fabricated using a vacuum evaporation apparatus; this layer is the electron injection layer 9. On the electron injection layer 9, a 15 nm thick Mg:Ag electrode layer is fabricated using a vacuum evaporation apparatus; the mass ratio of Mg to Ag is 1:9; this layer is used as the cathode layer 10. On the cathode layer 10, CP-1 is vacuum-deposited as the CPL layer 11 with a thickness of 70 nm. Organic electroluminescent device 1 is obtained.

[0208] The molecular structural formulas of the relevant materials are shown below:

[0209]

[0210]

[0211] After completing the OLED light-emitting device as described above, the anode and cathode were connected using a known driving circuit, and the voltage, current efficiency, and lifetime of the device were measured. Devices 2-32 and Comparative Examples 1-11, prepared using the same method, are shown in Table 2; the difference is that different N-type host materials were used to replace compound 1, and different P-type host materials were used to replace GH-2. The test results of the voltage, current efficiency, and lifetime of the obtained devices are shown in Table 3.

[0212] Table 2

[0213]

[0214]

[0215]

[0216] Table 3

[0217]

[0218] Note: Voltage and current efficiencies are based on a current density of 10 mA / cm². 2 The test was conducted under the following conditions using an IVL (current-voltage-brightness) testing system (Suzhou Fosstar Scientific Instruments Co., Ltd.); the lifetime testing system was the EAS-62C OLED device lifetime tester from System Technology Co., Ltd., Japan; LT95 refers to the condition at 20mA / cm². 2 The time it takes for the device brightness to decay to 95%.

[0219] As can be seen from the device data results in Table 3, compared with devices 1-11, the compounds of the present invention, when applied to devices, have a significantly lower device voltage than compounds Ref-1 to Ref-11, and the device efficiency and device lifetime are significantly improved compared with the comparative compounds Ref-1 to Ref-11, resulting in a significant improvement in the overall performance of OLED.

[0220] Comparing device embodiment 2 and device embodiment 32, and device embodiment 6 and device embodiment 20, it can be seen that deuteration has the effect of improving device lifespan.

[0221] In summary, the above are merely preferred embodiments of the present invention and are 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. A compound comprising a triazine and a carbazole structure, characterized in that, The structure of the compound is shown in general formula (1): General Formula (1) In general formula (1), X, X0, X1, X2, X3, X4 represent C-H, C-D or C atom; X5, X6, X7, X8 represent C-H or C-D; Y represents O atom or S atom; R represents hydrogen atom, phenyl, naphthyl or biphenyl; Ar represents phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl; A represents phenyl or N-phenyl indolyl; m represents 0 or 1; When R represents hydrogen atom, m represents 1, and Ar can only represent carbazolyl; All H atoms in general formula (1) can be independently deuterated.

2. The compound according to claim 1, wherein The structure of the compound is shown in general formula 1-1: General Formula 1-1 In general formula 1-1, X, X0, X1, X2, X3, X4 represent CH or C atom; X5, X6, X7, X8 represent C-H or C-D; Z1, Z2, Z3, Z4, Z5 represent C-H, C-D or C-Ph; Y represents O or S; Ar represents phenyl, biphenyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl; A represents phenyl or N-phenyl indolyl; m represents 0 or 1; All H atoms in general formula 1-1 can be independently deuterated.

3. The compound containing triazine and carbazole-based structure according to claim 2, characterized in that, The structure of the compound is shown in any one of general formula 2-1 to general formula 2-3: General formula 2-1 General formula 2-2 General formula 2-3 In general formula 2-1 to general formula 2-3, the definitions of Ar, A, Z1, Z2, Z3, Z4, Z5, Y are the same as defined in claim 2; and the site of attachment of the triazine is position 1, 2, 3, or 4; All H atoms in general formula 2-1 to general formula 2-3 can be independently deuterated.

4. The compound containing triazine and carbazole based structure according to claim 2, wherein The structure of the compound is shown in any one of general formula 3-1 to general formula 3-9: General formula 3-1 General formula 3-2 General formula 3-3 General formula 3-4 General formula 3-5 General formula 3-6 General formula 3-7 General formula 3-8 General formula 3-9 In general formula 3-1 to general formula 3-9, the definitions of Ar, A, Z1, Z2, Z3, Z4, Z5, Y are the same as defined in claim 2; and the site of attachment of the triazine is position 1, 2, 3, or 4; All H atoms in general formula 3-1 to general formula 3-9 can be independently deuterated.

5. The compound containing triazine and carbazole based structure according to claim 1, wherein The structure of the compound is shown in any one of general formula 4-1 to general formula 4-8: General formula 4-1 General formula 4-2 General formula 4-3 General formula 4-4 General formula 4-5 General formula 4-6 General formula 4-7 General formula 4-8 In general formula 4-1 to general formula 4-8, Y represents S or O atom.

6. The compound containing triazine and carbazole based structure according to claim 4, wherein The hydrogen atoms in the compound shown in general formula 3-1 to general formula 3-8 are all or partially replaced by deuterium.

7. The compound containing triazine and carbazole based structure according to claim 1, wherein The specific structure of the compound is any one of the following structures: 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97 98 99 100 101 102 103 104 105 106 107 108 129 130 131 132 133 134 135 136 139 140 143 144 147 148 153 154 155 156 157 158 159 160 161 162 163 164 165 166 167 168 169 170 171 172 173 174 175 176 177 178 179 180 181 182 183 184 185 186 187 188 189 190 191。 8. An organic electroluminescent device comprising a cathode, an anode and a functional layer, the functional layer being located between the cathode and the anode, characterized in that At least one functional layer contains the compound containing triazine and carbazole structure according to any one of claims 1 to 7; The functional layer includes a light-emitting layer, and the light-emitting layer contains the compound containing triazine and carbazole structure according to any one of claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that The light-emitting layer comprises a host material and a dopant material, and the host material contains the compound containing triazine and carbazole structure according to any one of claims 1 to 7.

10. The organic electroluminescent device according to claim 9, characterized in that, The host material of the light-emitting layer is formed by mixing the compound containing triazine and carbazole structure according to any one of claims 1-7 with any one or more of compounds GH-1 to GH-170, the specific structures of which are as follows: GH-1 GH-2 GH-3 GH-4 GH-5 GH-6 GH-7 GH-8 GH-9 GH-10 GH-11 GH-12 GH-13 GH-14 GH-15 GH-16 GH-17 GH-18 GH-19 GH-20 GH-21 GH-22 GH-23 GH-24 GH-25 GH-26 GH-27 GH-28 GH-29 GH-30 GH-31 GH-32 GH-33 GH-34 GH-35 GH-36 GH-37 GH-38 GH-39 GH-40 GH-41 GH-42 GH-43 GH-44 GH-45 GH-46 GH-47 GH-48 GH-49 GH-50 GH-51 GH-52 GH-53 GH-54 GH-55 GH-56 GH-57 GH-58 GH59 GH-60 GH-61 GH-62 GH-63 GH-64 GH-65 GH-66 GH-67 GH-68 GH-69 GH-70 GH-71 GH-72 GH-73 GH-74 GH-75 GH-76 GH-77 GH-78 GH-79 GH-80 GH-81 GH-82 GH-83 GH-84 GH-85 GH-86 GH-87 GH-88 GH-89 GH-90 GH-91 GH-92 GH-93 GH-94 GH-95 GH-96 GH-97 GH-98 GH-99 GH-100 GH-101 GH-102 GH-103 GH-104 GH-105 GH-106 GH-107 GH-108 GH-109 GH-110 GH-111 GH-112 GH-113 GH-114 GH-115 GH-116 GH-117 GH-118 GH-119 GH-120 GH-121 GH-122 GH-123 GH-124 GH-125 GH-126 GH-127 GH-128 GH-129 GH-130 GH-131 GH-132 GH-133 GH-134 GH-135 GH-136 GH-137 GH-138 GH-139 GH-140 GH-141 GH-142 GH-143 GH-144 GH-145 GH-146 GH-147 GH-148 GH-149 GH-150 GH-151 GH-152 GH-153 GH-154 GH-155 GH-156 GH-157 GH-158 GH-159 GH-160 GH-161 GH-162 GH-163 GH-164 GH-165 GH-166 GH-167 GH-168 GH-169 GH-170.

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