Deuterated compound and organic light-emitting device containing deuterated compound

Abstract

The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a deuterated compound and an organic light-emitting device containing the deuterated compound. According to the compound provided by the invention, a combined structure of adamantane-substituted deuterated aryl and polycyclic aryl is adopted, so that the hole transport performance of the compound is improved, the stability and the charge transport capability are improved, the stability of a device is effectively improved, and the service life of the device is effectively prolonged.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescent materials technology, specifically relating to a deuterated compound and an organic light-emitting device containing the same. Background Technology

[0002] Currently, organic light-emitting diodes (OLEDs), as a new generation of display technology, have advantages such as ultra-thinness, self-illumination, wide viewing angle, fast response, high luminous efficiency, good temperature adaptability, simple manufacturing process, low driving voltage, and low energy consumption. They have been widely used in industries such as flat panel displays, flexible displays, solid-state lighting, and automotive displays.

[0003] Organic light-emitting devices typically consist of an anode, a cathode, and an organic material layer between them. The organic material layer is usually formed in a multilayer structure composed of different materials to improve the brightness, efficiency, and lifetime of organic electroluminescent devices. The organic material layer can be composed of hole injection layer, hole transport layer, light-emitting layer, electron transport layer, and electron injection layer, etc.

[0004] For organic light-emitting diodes (OLEDs), the luminescent material plays a crucial role in the device efficiency. The luminescent layer material can be either a host material or a guest material. In OLEDs, the luminescent layer is typically a combination of host and dopant materials to improve color purity, luminous efficiency, and stability. However, when using this dopant / host material combination as the luminescent layer, the host material has a significant impact on the efficiency and lifetime of the OLED. Therefore, it is necessary to continuously develop novel host materials for OLEDs that offer high efficiency, long lifetime, and are suitable for mass production. Summary of the Invention

[0005] To address the shortcomings of existing technologies, this invention provides a deuterated compound and an organic light-emitting device comprising the same. The compound provided by this invention employs adamantane-substituted deuterated aryl group for substitution, retains the hydrogen-substituted core unit, and introduces a hole-transporting unit (dibenzofuran or dibenzothiophene) at the end. This improves the hole transport performance, stability, and charge transport capability of the compound, thereby effectively enhancing the stability and lifetime of the device.

[0006] A deuterated compound having the structure shown in Formula 1:

[0007] R5 is selected from substituted or unsubstituted C. 6-30 aryl, substituted or unsubstituted C 6-30 Aromatic amino groups, substituted or unsubstituted C 6-30 heteroaryl; L1 is selected from direct bond or C 6-30 The deuterated aryl group, L2 is selected from the direct bond or phenyl group;

[0008] L1 is C6-30 In the case of deuterated aryl groups, R1 to R4 and R6 to R9 may be the same or different from each other, and each may be hydrogen or deuterium independently;

[0009] When L1 is a direct bond, R1 to R4 and R6 to R9 are selected from deuterium.

[0010] C 6-30 In deuterated aryl groups, all hydrogen atoms on the aryl group are replaced by deuterium.

[0011] The L1 is selected from direct bonds, deuterated phenyl, deuterated biphenyl, and deuterated aryl groups having 2-3 phenyl fused groups. Examples of aryl groups having 2-3 phenyl fused groups include naphthyl and anthracene.

[0012] Preferably, the first formula has the structural formulas shown in formulas 1-1 to 1-4:

[0013]

[0014] Preferably, in formulas 1-2, 1-3, and 1-4, R1 to R4 and R6 to R9 are deuterium.

[0015] The C 6-30 Heteroaryl groups have at least one C 5-6 Heterocyclic compounds.

[0016] More specifically, the heteroaryl group having 1-2 phenyl groups has a five-membered heterocycle, which is connected to the phenyl group by a carbon-carbon covalent bond, including carbazole, furan, thiophene, etc., but not limited to these.

[0017] The C 6-30 Heteroaryl groups have the structural formula shown in Formula 2-4: R 10 To R 13 They may be the same as or different from each other, and each is independently H, cyano, halogen, C. 1-5 alkyl, C 6-12 aryl, R 10 To R 13 Any two adjacent elements can combine to form a ring, where X is selected from N-ph, O, or S; and Y is independently selected from N and CR. 16 R 16 The Y atoms are hydrogen or phenyl, and at least 1-3 Y atoms are N; * indicates the connection site between Formula 2 and Formula 1.

[0018] X is selected from O or S, and R 10 To R 13 Any two adjacent points in the ring can combine to form a ring. Furthermore, they can combine to form an aromatic ring. Even further, R... 10 To R 13 Any two adjacent molecules can combine to form a phenyl group.

[0019] The R 10 To R 13 They are the same or different from each other, and each is independently H and C. 1-5 Alkyl and phenyl groups.

[0020] The R 10 To R 13 They may be the same as or different from each other and are independently H, cyano, halogen, or phenyl.

[0021] Formula 3 is selected from: m is selected from 0, 1, or 2, R 16 It is a phenyl group.

[0022] The substituted or unsubstituted C 6-30 The aromatic amino group has the following structural formula: *-L2-NR 14 R 15 The L2 is selected from direct bonds or phenyl groups, and the R... 14 R 15 The same or different ones are selected from aryl or heteroaryl groups having 1-2 phenyl groups.

[0023] Here, heteroaryl refers to aryl groups containing heteroatoms, such as N, O, and S atoms.

[0024] The C 6-30 The aryl group is selected from phenyl groups or polycyclic aryl groups having 2-4 phenyl groups connected by direct bonds or C-terminal bonds. 1-3 It is connected in any one or more ways, either alkyl or carbon-carbon covalent bonds.

[0025] The C 6-30 The aryl group is selected from the group consisting of one or more of the following groups:

[0026]

[0027] * indicates the connection point with Equation 1.

[0028] The compound:

[0029]

[0030]

[0031]

[0032]

[0033]

[0034] The above compounds can generally be prepared using a method that includes the following steps:

[0035] 1) 1-Adamantanol reacts with a haloaryl group to give intermediate 1, intermediate 1 undergoes a deuteration reaction with deuterated water to give intermediate 2, and intermediate 2 undergoes a borate reaction with pinarate diboronate to give intermediate A.

[0036] 2) Intermediate A reacts with a halogenated intermediate to give intermediate 3, and intermediate 3 undergoes a borate reaction with pinarate diboronate to give intermediate C.

[0037] 3) Intermediate A (or intermediate C) reacts with the halide via the Suzuki reaction to yield the compound shown in Formula 1.

[0038] In addition, the organic light-emitting device according to the present invention includes a first electrode; a second electrode disposed opposite to the first electrode; and an organic light-emitting device including at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one layer of the organic material layer contains the aforementioned deuterated compound.

[0039] The organic light-emitting device of the present invention can be manufactured using conventional organic light-emitting device manufacturing methods and materials, the difference being that the above-mentioned deuterated compound is used to form one or more layers of organic material.

[0040] When manufacturing organic light-emitting devices, compounds can be used to form organic material layers through solution coating and vacuum deposition. Here, solution application methods refer to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but are not limited to these.

[0041] The organic material layer of the organic light-emitting device of the present invention can have a single-layer structure or a multi-layer structure in which two or more organic material layers are stacked.

[0042] In the organic light-emitting device of the present invention, the first electrode is a cathode and the second electrode is an anode.

[0043] In the organic light-emitting device of the present invention, the organic material layer may include a hole injection layer, a hole transport layer, a layer that simultaneously performs hole injection and hole transport, a light-emitting layer, an electron injection layer, an electron transport layer, and a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited to this and may include fewer or more organic material layers. Furthermore, one or more of these layers may contain a deuterated compound as indicated.

[0044] As the anode of the present invention, a material with a high work function is preferred. The anode can be a transmission electrode, a reflection electrode, or a semi-transmission electrode. When the anode is a transmission electrode, the material used to form the anode can be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof; when the anode is a semi-transmission electrode or a reflection electrode, the material used to form the anode can be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof. The anode can have a single-layer structure or a multilayer structure including two or more layers. For example, the anode can have a single-layer structure of Al or a three-layer structure of ITO / Ag / ITO, but the structure of the anode is not limited to these.

[0045] As the hole injection layer described in this invention, a material with a high work function is preferred. It can be a monolayer structure composed of a single substance, or a monolayer or multilayer structure composed of different substances. The hole injection layer is used to facilitate the injection of holes from the anode to the light-emitting layer. The hole injection material is a material that can effectively inject holes from the anode at low voltage. The molecular orbitals of the hole injection material are preferably located between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine organic materials, hexanitrile hexaazabenzophenanthrene organic materials, quinacridone organic materials and perylene organic materials, anthraquinones, polyaniline and polythiophene conductive polymers, etc.

[0046] As the hole transport layer described in this invention, a material with high hole mobility is preferred. It can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. It can be selected from any one or more of the following structures: carbazole derivatives, triarylamine derivatives, biphenyl diamine derivatives, fluorene derivatives, stilbene derivatives, phthalocyanine compounds, hexanitrile hexaazabenzophenanthrene compounds, quinacridone compounds, anthraquinone compounds, polyaniline, polythiophene, polyvinylcarbazole, etc., but is not limited thereto.

[0047] The organic material layer includes a light-emitting layer, and the light-emitting layer includes a deuterated compound represented by Formula 1.

[0048] As the light-emitting layer described in this invention, it may contain only guest materials, or it may be in the form of guest materials dispersed in host materials, and may contain multiple host materials and multiple dopants.

[0049] The light-emitting layer can emit red, green, or blue light and can be made of phosphorescent or fluorescent materials.

[0050] The luminescent layer comprises a deuterated compound represented by Formula 1 as the main component and an organic compound as a dopant.

[0051] The optimal ratio of the doping ratio of the host material and the guest material of the light-emitting layer can vary depending on the material used. Typically, the doping ratio of the guest material of the light-emitting layer is 0.01% to 20% by weight, preferably 0.1% to 15%, and more preferably 1% to 10%.

[0052] As the hole-blocking layer described in this invention, the preferred material is one that can effectively block holes. It can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. It can be selected from any one or more of the following structures: phenanthroline derivatives, rare earth derivatives, oxazole derivatives, triazole derivatives, triazine derivatives, etc., but is not limited thereto.

[0053] As the electron transport layer described in this invention, a material with high electron mobility is preferred. It can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. It can be selected from any one or more of the following structures: metal complexes, imidazole derivatives, carbazole derivatives, benzimidazole derivatives, quinoline derivatives, triazoles, phenanthroline derivatives, etc., but is not limited thereto.

[0054] As the electron injection layer described in this invention, a material with a low work function is preferred. It can be a single-layer structure composed of a single substance, or a single-layer or multi-layer structure composed of different substances. It can be selected from one or more of the following structures: alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, and other substances with high electron injection properties, but is not limited thereto.

[0055] As the cathode described in this invention, a material with a low work function is preferred. The cathode can be a transmission electrode, a semi-reflective electrode, or a reflective electrode. When the cathode is a transmission electrode, the material used to form the cathode can be selected from transparent metal oxides (e.g., ITO, IZO, etc.); when the cathode is a semi-reflective electrode or a reflective electrode, the material used to form the cathode can be selected from Ag, Mg, Cu, Al, Pt, Pd, Au, Ni, Nd, Ir, Cr, Li, Ca, LiF / Ca, LiF / Al, Mo, Ti, compounds including them, or mixtures thereof (e.g., mixtures of Ag and Mg), but is not limited thereto.

[0056] There are no particular limitations on the preparation method of each thin film in the organic electroluminescent device described in this invention. Vacuum evaporation, sputtering, spin coating, spraying, screen printing, laser transfer, etc., can be used, but are not limited to these methods.

[0057] The organic electroluminescent device described in this invention is mainly used in the field of information display technology. It is widely used in various information displays, such as tablet computers, flat-screen TVs, mobile phones, smartwatches, digital cameras, VR, in-vehicle systems, wearable devices, etc. Detailed Implementation

[0058] The principles and features of the present invention are described below. The embodiments given are for illustrative purposes only and are not intended to limit the scope of the invention. Unless otherwise specified in the embodiments, conventional conditions or conditions recommended by the manufacturer should be followed. Reagents or instruments used, unless otherwise specified, are all commercially available conventional products.

[0059] Preparation of intermediate A-1:

[0060]

[0061] 1-Adamantanol (15.22 g, 100 mmol), bromobenzene (15.7 g, 100 mmol), and dichloromethane (DCM, 150 mL) were added to a round-bottom flask, and the mixture was cooled to -5 °C under nitrogen protection. Trifluoromethanesulfonic acid (22.51 g, 150 mmol) was added dropwise at -5 °C, and the mixture was stirred for 3 h. Deionized water (100 mL) was added to the reaction mixture and the mixture was washed until pH = 7. Dichloromethane (50 mL) was added for extraction. The organic phases were combined, dried using anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain 4-adamantylbromobenzene (15.44 g, 53%).

[0062] 4-Adamantylbromobenzene (14.56 g; 50 mmol), trifluoromethanesulfonic acid (0.8 g; 5 mmol), deuterium water (20.03 g; 1 mol), and 1,4-dioxane (250 mL) were added to a round-bottom flask and stirred at 100 °C–105 °C for 36 hours under nitrogen protection. After cooling to room temperature, ammonium chloride aqueous solution (100 mL) and dichloromethane (150 mL) were added to the reaction solution. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give intermediate a-1 (8.27 g, 56%).

[0063] Intermediate a-1 (5.91 g; 20 mmol), pinacol diborate (5.08 g; 20 mmol), tris(dibenzylacetone)palladium (0.19 g, 0.2 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.16 g, 0.4 mmol), potassium carbonate K2CO3 (13.82 g, 40 mmol), and 1,4-dioxane (250 mL) were added to a round-bottom flask. The mixture was stirred at 90 °C for 3 hours under nitrogen protection. After cooling to room temperature, a mixture of water and dichloromethane was added to the reaction solution for extraction. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was purified to give intermediate A-1 (5.41 g, 79%). Mass spectrometer: MALDI-TOF-MS (m / z) = 342.29 (C, 77.18; H, 10.29; B, 3.18; O, 9.35). Preparation of intermediate A-2:

[0064]

[0065] 1-Adamantanol (15.22 g, 100 mmol), bromonaphthalene (20.71 g, 100 mmol), and dichloromethane (DCM, 150 mL) were added to a round-bottom flask. The mixture was cooled to -5 to 0 °C under nitrogen protection. Trifluoromethanesulfonic acid (22.51 g, 150 mmol) was added dropwise at -5 to 0 °C, and the mixture was stirred for 3 h. Deionized water (100 mL) was added to the reaction mixture and the solution was washed until pH = 7. Dichloromethane (50 mL) was added for extraction. The organic phases were combined, dried using anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain 1-bromo-4-adamantanenaphthalene (19.79 g, 58%).

[0066] 1-Bromo-4-adamantylnaphthalene (17.06 g; 50 mmol), trifluoromethanesulfonic acid (0.8 g; 5 mmol), deuterium water (20.03 g; 1 mol), and 1,4-dioxane (22.03 g; 250 mL) were added to a round-bottom flask and stirred at 100 °C–105 °C for 36 hours under nitrogen protection. After cooling to room temperature, ammonium chloride aqueous solution (100 mL) and dichloromethane (150 mL) were added to the reaction solution. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give intermediate a-2 (9.03 g, 52%).

[0067] Intermediate a-2 (6.95 g; 20 mmol), pinacol diborate (5.08 g; 20 mmol), tris(dibenzylacetone)palladium (0.19 g, 0.2 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.16 g, 0.4 mmol), potassium carbonate K2CO3 (13.82 g, 40 mmol), and 1,4-dioxane (250 mL) were added to a round-bottom flask. The mixture was stirred at 90 °C for 3 hours under nitrogen protection. After cooling to room temperature, a mixture of water and dichloromethane was added to the reaction solution for extraction. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was purified to give intermediate A-2 (5.6 g, 71%). Mass spectrometer: MALDI-TOF-MS (m / z) = 394.35 (C, 79.19; H, 9.95; B, 2.74; O, 8.11). Preparation of intermediate A-3:

[0068]

[0069] 1-Adamantanol (15.22 g, 100 mmol), 4-bromobiphenyl (23.31 g, 100 mmol), and dichloromethane (DCM, 150 mL) were added to a round-bottom flask and cooled to -5 to 0 °C under nitrogen protection. Trifluoromethanesulfonic acid (22.51 g, 150 mmol) was added dropwise at -5 to 0 °C, and the mixture was stirred for 3 h. Deionized water (100 mL) was added to the reaction solution and the mixture was washed until pH = 7. Dichloromethane (50 mL) was added for extraction. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure to obtain 1-(4'-bromo-[1,1'-biphenyl]-4-yl)adamantane (20.20 g, 55%).

[0070] 1-(4'-bromo-[1,1'-biphenyl]-4-yl)adamantane (18.37 g; 50 mmol), trifluoromethanesulfonic acid (0.8 g; 5 mmol), deuterium water (20.03 g; 1 mol), and 1,4-dioxane (22.03 g; 250 mL) were added to a round-bottom flask and stirred at 100 °C–105 °C for 36 hours under nitrogen protection. After cooling to room temperature, ammonium chloride aqueous solution (100 mL) and dichloromethane (150 mL) were added to the reaction solution. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to obtain intermediate a-3 (9.38 g, 50%).

[0071] Intermediate a-3 (7.51 g; 20 mmol), pinacol diborate (5.08 g; 20 mmol), tris(dibenzylacetone)palladium (0.19 g, 0.2 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.16 g, 0.4 mmol), potassium carbonate K2CO3 (13.82 g, 40 mmol), and 1,4-dioxane (250 mL) were added to a round-bottom flask. The mixture was stirred at 90 °C for 3 hours under nitrogen protection. After cooling to room temperature, a mixture of water and dichloromethane was added to the reaction solution for extraction. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was purified to give intermediate A-3 (5.75 g, 68%). Mass spectrometer: MALDI-TOF-MS (m / z) = 422.36 (C, 79.61; H, 10.27; B, 2.57; O, 7.55). Preparation of intermediate A-4:

[0072]

[0073] 1-Adamantaneol (15.22 g, 100 mmol), 9-bromoanthracene (25.71 g, 100 mmol), and dichloromethane (DCM, 150 mL) were added to a round-bottom flask. The mixture was cooled to -5 to 0 °C under nitrogen protection. Trifluoromethanesulfonic acid (22.51 g, 150 mmol) was added dropwise at -5 to 0 °C, and the mixture was stirred for 3 h. Deionized water (100 mL) was added to the reaction mixture and the solution was washed until pH = 7. Dichloromethane (50 mL) was added for extraction. The organic phases were combined, dried using anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The crude product was purified by silica gel column chromatography using n-heptane as the mobile phase to obtain 9-bromo-10-adamantaneanthracene (20.35 g, 52%).

[0074] 9-Bromo-10-adamantane anthracene (19.57 g; 50 mmol), trifluoromethanesulfonic acid (0.8 g; 5 mmol), deuterium water (20.03 g; 1 mol), and 1,4-dioxane (22.03 g; 250 mL) were added to a round-bottom flask and stirred at 100 °C–105 °C for 36 hours under nitrogen protection. After cooling to room temperature, ammonium chloride aqueous solution (100 mL) and dichloromethane (150 mL) were added to the reaction solution. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give intermediate a-4 (11.38 g, 57%).

[0075] Intermediate a-4 (6.95 g; 20 mmol), pinacol diborate (5.08 g; 20 mmol), tris(dibenzylacetone)palladium (0.19 g, 0.2 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.16 g, 0.4 mmol), potassium carbonate K2CO3 (13.82 g, 40 mmol), and 1,4-dioxane (250 mL) were added to a round-bottom flask. The mixture was stirred at 90 °C for 3 hours under nitrogen protection. After cooling to room temperature, a mixture of water and dichloromethane was added to the reaction solution for extraction. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was purified to give intermediate A-1 (6.7 g, 75%). Mass spectrometer: MALDI-TOF-MS (m / z) = 446.40 (C, 80.70; H, 9.70; B, 2.42; O, 7.18). Preparation of intermediate C-1:

[0076]

[0077] Intermediate A-1 (27.39 g; 80 mmol), 9-bromoanthracene (22.63 g; 88 mmol), tris(dibenzylideneacetone)palladium (0.76 g; 0.8 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.66 g, 1.6 mmol), and potassium carbonate K2CO3 (22.11 g, 160 mmol) were added to 400 mL of 1,4-dioxane. The mixture was heated to 108 °C under nitrogen protection and stirred for 3 h. After cooling to room temperature, 90 mL of water was added, the mixture was separated, the organic phase was collected and concentrated, ethanol was added, the mixture was slurried, filtered, and dried under vacuum to obtain intermediate c-1 (18.22 g, yield 58%).

[0078] Intermediate c-1 (15.7 g; 40 mmol) was added to 400 mL of N,N-dimethylformamide (DMF), cooled to 0 °C under nitrogen protection, stirred, and then N-bromosuccinimide (7.83 g; 44 mmol) was added; the temperature was then raised to 25 °C and reacted for 2 h; after the reaction was completed, 400 mL of sodium metabisulfite aqueous solution (200 g / mL) was added to the reaction solution and stirred for 1 h, filtered, and ethanol was added to the filter cake and stirred at 25 °C for 1 h, filtered, and vacuum dried for 15 h to obtain intermediate c-2 (14.71 g, yield 78%).

[0079] Intermediate C-2 (9.43 g; 20 mmol), pinacol diborate (5.59 g; 22 mmol), tris(dibenzylacetone)palladium (0.19 g, 0.2 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.16 g, 0.4 mmol), potassium carbonate K2CO3 (4.15 g, 30 mmol), and 1,4-dioxane (90 mL) were added to a round-bottom flask. Under nitrogen protection, the mixture was stirred at 90 °C for 3 hours. After cooling to room temperature, 45 mL of toluene and 90 mL of water were added to the reaction mixture. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to obtain intermediate C-1 (6.43 g, 62%). Mass spectrometer: MALDI-TOF-MS (m / z) = 518.48 (C, 83.40; H, 8.35; B, 2.08; O, 6.17).

[0080] Preparation of intermediate C-2:

[0081]

[0082] Intermediate A-2 (31.55 g; 80 mmol), 9-bromoanthracene (22.63 g; 88 mmol), tris(dibenzylacetone)palladium (0.76 g; 0.8 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.66 g, 1.6 mmol), and potassium carbonate K2CO3 (10.37 g, 75 mmol) were added to 400 mL of 1,4-dioxane. The mixture was heated to 108 °C under nitrogen protection and stirred for 3 h. After cooling to room temperature, 200 mL of toluene and 200 mL of water were added to the reaction mixture. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to obtain intermediate C-3 (18.14 g, yield 51%).

[0083] Intermediate c-3 (17.79 g; 40 mmol) was added to 400 mL of N,N-dimethylformamide (DMF), cooled to 0 °C under nitrogen protection, stirred, and then N-bromosuccinimide (7.83 g; 44 mmol) was added; the temperature was then raised to 25 °C and reacted for 2 h; after the reaction was completed, 400 mL of sodium metabisulfite aqueous solution (200 g / mL) was added to the reaction solution and stirred for 1 h, filtered, and ethanol was added to the filter cake and stirred at 25 °C for 1 h, filtered, and vacuum dried for 15 h to obtain intermediate c-2 (15.71 g, yield 75%).

[0084] Intermediate C-4 (10.47 g; 20 mmol), pinacol diborate (5.08 g; 20 mmol), tris(dibenzylacetone)dipalladium (0.19 g, 0.2 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.16 g, 0.4 mmol), and potassium carbonate (K₂CO₃) (4.15 g, 30 mmol) were added to a round-bottom flask. The mixture was stirred at 90 °C for 3 hours under nitrogen protection. After cooling to room temperature, a mixture of water and dichloromethane was added to the reaction solution for extraction. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The purified solution yielded intermediate C-2 (7.3 g, 64%). Mass spectrometry: MALDI-TOF-MS (m / z) = 570.53 (C, 84.20; H, 8.28; B, 1.90; O, 5.62).

[0085] Preparation of intermediate C-3:

[0086]

[0087] Intermediate A-3 (33.8 g; 80 mmol), 9-bromoanthracene (22.63 g; 88 mmol), tris(dibenzylacetone)dipalladium (0.76 g; 0.8 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.66 g, 1.6 mmol), and potassium carbonate K2CO3 (10.37 g, 75 mmol) were added to 400 mL of 1,4-dioxane. The mixture was heated to 108 °C under nitrogen protection and stirred for 3 h. After cooling to room temperature, 200 mL of toluene and 200 mL of water were added to the reaction mixture. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to obtain intermediate C-5 (16.27 g, 59% yield).

[0088] Intermediate c-5 (18.91 g; 40 mmol) was added to 400 mL of N,N-dimethylformamide (DMF), cooled to 0 °C under nitrogen protection, stirred, and then N-bromosuccinimide (7.83 g; 44 mmol) was added; the temperature was then raised to 25 °C and reacted for 2 h; after the reaction was completed, 400 mL of sodium metabisulfite aqueous solution (200 g / mL) was added to the reaction solution and stirred for 1 h, filtered, and ethanol was added to the filter cake and stirred at 25 °C for 1 h, filtered, and vacuum dried for 15 h to obtain intermediate c-6 (16.99 g, yield 77%).

[0089] Intermediate C-6 (11.03 g; 20 mmol), pinacol diborate (5.08 g; 20 mmol), tris(dibenzylacetone)palladium (0.19 g, 0.2 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.16 g, 0.4 mmol), and potassium carbonate K₂CO₃ (4.15 g, 30 mmol) were added to a round-bottom flask. The mixture was stirred at 90 °C for 3 hours under nitrogen protection. After cooling to room temperature, a mixture of water and dichloromethane was added to the reaction solution for extraction. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The purified compound yielded intermediate C-3 (7.78 g, 65%). Mass spectrometry: MALDI-TOF-MS (m / z) = 598.47 (C, 84.27; H, 8.58; B, 1.79; O, 5.35).

[0090] Synthesis Example 1: Synthesis of Compound 1

[0091]

[0092] Intermediate A-1 (17.12 g; 50 mmol), intermediate B-1 (16.66 g; 50 mmol), tris(dibenzylacetone)palladium (0.48 g; 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.41 g; 1 mmol), and potassium carbonate K2CO3 (10.37 g; 75 mmol) were added to 400 mL of 1,4-dioxane. The mixture was heated to 108 °C under nitrogen protection and stirred for 3 h. After cooling to room temperature, 200 mL of toluene and 200 mL of water were added to the reaction mixture. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to give compound 1 (17.11 g, 73% yield). Mass spectrometry: MALDI-TOF-MS (m / z) = 468.51 (C, 92.24; H, 7.76).

[0093] Synthesis Example 2: Synthesis of Compound 2

[0094]

[0095] 1-(3-bromophenyl)adamantane (14.56 g; 50 mmol), trifluoromethanesulfonic acid (0.8 g; 5 mmol), deuterium water (20.03 g; 1 mol), and 1,4-dioxane (22.03 g; 250 mL) were added to a round-bottom flask and stirred at 100 °C–105 °C for 36 hours under nitrogen protection. After cooling to room temperature, ammonium chloride aqueous solution (100 mL) and dichloromethane (150 mL) were added to the reaction solution. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give intermediate a-5 (9.15 g, 62%).

[0096] Intermediate a-5 (8.86 g; 30 mmol), pinacol diborate (8.38 g; 33 mmol), tris(dibenzylacetone)palladium (0.29 g, 0.3 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.25 g, 0.6 mmol), potassium carbonate K2CO3 (8.29 g, 60 mmol), and 1,4-dioxane (250 mL) were added to a round-bottom flask. The mixture was stirred at 90 °C for 3 hours under nitrogen protection. After cooling to room temperature, a mixture of water and dichloromethane was added to the reaction solution for extraction. The organic phase was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The mixture was purified to give intermediate A-5 (7.5 g, 73%).

[0097] Intermediate A-5 (3.42 g; 10 mmol), intermediate B-1 (3.67 g; 11 mmol), tris(dibenzylacetone)palladium (0.2 g; 0.2 mmol), 0.1 g 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl, and potassium carbonate K2CO3 (2.07 g, 15 mmol) were added to 400 mL of 1,4-dioxane. The mixture was heated to 108 °C under nitrogen protection and stirred for 3 h. After cooling to room temperature, 200 mL of toluene and 200 mL of water were added to the reaction mixture. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to give compound 2 (3.47 g, 74% yield). Mass spectrometry: MALDI-TOF-MS (m / z) = 468.31 (C, 92.27; H, 7.73).

[0098] Synthesis Example 3: Synthesis of Compound 12

[0099]

[0100] Intermediate A-1 (17.12 g; 50 mmol), intermediate B-2 (21.17 g; 50 mmol), tris(dibenzylideneacetone)palladium (0.48 g; 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.41 g; 1 mmol), and potassium carbonate K₂CO₃ (10.37 g; 75 mmol) were added to 400 mL of 1,4-dioxane under nitrogen atmosphere. The mixture was heated to 108°C under protective conditions and stirred for 3 hours. Then it was cooled to room temperature, and 200 mL of toluene and 200 mL of water were added to the reaction solution. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to obtain compound 12 (19.56 g, 70% yield). Mass spectrometry: MALDI-TOF-MS (m / z) = 558.53 (C, 90.28; H, 6.84; O, 2.87).

[0101] Synthesis Example 4: Synthesis of Compound 24

[0102]

[0103] Intermediate C-1 (25.93 g; 50 mmol), 2-bromo-8-phenyl-dibenzothiophene (16.96 g; 50 mmol), tris(dibenzylideneacetone)dipalladium (0.16 g; 0.2 mmol), tris(dibenzylideneacetone)dipalladium (0.48 g; 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.41 g; 1 mmol), and potassium carbonate K2CO3 (10.37 g; 75 mmol) were added In 400 mL of 1,4-dioxane, the mixture was heated to 108 °C under nitrogen protection and stirred for 3 h. After cooling to room temperature, 200 mL of toluene and 200 mL of water were added to the reaction mixture. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to obtain compound 24 (23.76 g, yield 73%). Mass spectrometry: MALDI-TOF-MS (m / z) = 650.83 (C, 88.56; H, 6.49; S, 4.95).

[0104] Synthesis Example 5: Synthesis of Compound 29

[0105]

[0106] Intermediate C-2 (28.53 g; 50 mmol), 1-bromophenanthrene (12.86 g; 50 mmol), tris(dibenzylacetone)palladium (0.48 g; 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.41 g, 1 mmol), and potassium carbonate K2CO3 (10.37 g, 75 mmol) were added to 400 mL of 1,4-dioxane. The mixture was heated to 108 °C under nitrogen protection and stirred for 3 h. After cooling to room temperature, 200 mL of toluene and 200 mL of water were added to the reaction mixture. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to give compound 29 (23.59 g, 76% yield). Mass spectrometry: MALDI-TOF-MS (m / z) = 620.42 (C, 92.85; H, 7.15).

[0107] Synthesis Example 6: Synthesis of Compound 32

[0108]

[0109] Intermediate C-2 (28.53 g; 50 mmol), 1-bromo-3,5-diphenylbenzene (15.46 g; 50 mmol), tris(dibenzylideneacetone)dipalladium (0.48 g; 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.41 g; 1 mmol), and potassium carbonate K2CO3 (10.37 g; 75 mmol) were added to 400 mL of 1,4-dioxane. The mixture was heated to 108 °C under nitrogen protection and stirred for 3 h. After cooling to room temperature, 200 mL of toluene and 200 mL of water were added to the reaction mixture. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to give compound 32 (24.9 g, 74% yield). Mass spectrometry: MALDI-TOF-MS (m / z) = 672.61 (C, 92.83; H, 7.17).

[0110] Synthesis Example 7: Synthesis of Compound 36

[0111]

[0112] Intermediate C-2 (28.53 g; 50 mmol), 2-bromo-4,6-diphenyl-1,3,5-triazine (15.61 g; 50 mmol), tris(dibenzylideneacetone)dipalladium (0.48 g; 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.41 g; 1 mmol), and potassium carbonate K2CO3 (10.37 g; 75 mmol) were added to 400 mL of 1,4-diphenyltriazine. In the oxane, the mixture was heated to 108°C under nitrogen protection and stirred for 3 h; then cooled to room temperature, and 200 mL of toluene and 200 mL of water were added to the reaction solution. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to give compound 36 (25.01 g, yield 74%). Mass spectrometry: MALDI-TOF-MS (m / z) = 675.83 (C, 87.02; H, 6.73; N, 6.25). Synthesis Example 8: Synthesis of Compound 40

[0113]

[0114] Intermediate C-2 (28.53 g; 50 mmol), 2-bromodibenzothiophene (13.16 g; 50 mmol), tris(dibenzylideneacetone)palladium (0.48 g; 0.5 mmol), 2-dicyclohexylphospho-2',6'-dimethoxybiphenyl (0.41 g; 1 mmol), and potassium carbonate K₂CO₃ (10.37 g; 75 mmol) were added to 400 mL of 1,4-dioxane. The mixture was heated to 108°C under gas protection and stirred for 3 hours. Then it was cooled to room temperature, and 200 mL of toluene and 200 mL of water were added to the reaction solution. The mixture was separated, and the organic phase was dried with anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to obtain compound 40 (21.63 g, yield 69%). Mass spectrometry: MALDI-TOF-MS (m / z) = 626.31 (C, 88.12; H, 6.74; S, 5.13).

[0115] Synthesis Example 9: Synthesis of Compound 42

[0116]

[0117] Intermediate C-2 (28.53 g; 50 mmol), 3-bromo-N-phenylcarbazole (16.11 g; 50 mmol), tris(dibenzylacetone)palladium (0.48 g; 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.41 g; 1 mmol), and potassium carbonate K2CO3 (10.37 g; 75 mmol) were added to 400 mL of 1,4-dioxane. The mixture was heated to 108°C under nitrogen protection and stirred for 3 hours. Then it was cooled to room temperature, and 200 mL of toluene and 200 mL of water were added to the reaction solution. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to obtain compound 42 (26.41 g, yield 77%). Mass spectrometry: MALDI-TOF-MS (m / z) = 685.79 (C, 91.06; H, 6.92; N, 2.02).

[0118] Synthesis Example 10: Synthesis of Compound 51

[0119]

[0120] Intermediate C-3 (29.93 g; 50 mmol), intermediate B-1 (16.66 g; 50 mmol), tris(dibenzylideneacetone)dipalladium (0.48 g; 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.41 g; 1 mmol), and potassium carbonate K2CO3 (10.37 g; 75 mmol) were added to 400 mL of 1,4-dioxane. The mixture was heated to 108 °C under nitrogen protection and stirred for 3 h. After cooling to room temperature, 200 mL of toluene and 200 mL of water were added to the reaction mixture. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to obtain compound 51 (19.48 g, 71% yield). Mass spectrometry: MALDI-TOF-MS (m / z) = 548.51 (C, 91.90; H, 8.10).

[0121] Synthesis Example 11: Synthesis of Compound 61

[0122]

[0123] Intermediate C-3 (29.93 g; 50 mmol), 4-bromo-9,9-dimethylpentane (13.66 g; 50 mmol), tris(dibenzylideneacetone)dipalladium (0.48 g; 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.41 g; 1 mmol), and potassium carbonate K2CO3 (10.37 g; 75 mmol) were added to 400 mL of 1,4-dioxane. In the hexacyclic compound, the mixture was heated to 108 °C under nitrogen protection and stirred for 3 h. Then, it was cooled to room temperature, and 200 mL of toluene and 200 mL of water were added to the reaction solution. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to obtain compound 61 (24.94 g, yield 75%). Mass spectrometry: MALDI-TOF-MS (m / z) = 664.43 (C, 92.15; H, 7.85).

[0124] Synthesis Example 12: Synthesis of Compound 62

[0125]

[0126] Intermediate C-3 (29.93 g; 50 mmol), 2-bromobenzo[B]naphtho[2,3-D]furan (14.86 g; 50 mmol), tris(dibenzylideneacetone)dipalladium (0.48 g; 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.41 g; 1 mmol), and potassium carbonate K2CO3 (10.37 g; 75 mmol) were added to 400 mL of 1,4-dioxane. In the hexacyclic compound, the mixture was heated to 108°C under nitrogen protection and stirred for 3 hours. After cooling to room temperature, 200 mL of toluene and 200 mL of water were added to the reaction mixture. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to obtain compound 62 (25.49 g, yield 74%). Mass spectrometry: MALDI-TOF-MS (m / z) = 688.57 (C, 90.65; H, 7.03; O, 2.32). Synthesis Example 13: Synthesis of Compound 80

[0127]

[0128] Intermediate A-4 (22.32 g; 50 mmol), 2-bromobenzo[9,10]phenanthrene (15.36 g; 50 mmol), tris(dibenzylideneacetone)dipalladium (0.48 g; 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.41 g; 1 mmol), and potassium carbonate K2CO3 (10.37 g; 75 mmol) were added to 400 mL of 1,4-dioxane. In the hexacyclic compound, the mixture was heated to 108 °C under nitrogen protection and stirred for 3 h. After cooling to room temperature, 200 mL of toluene and 200 mL of water were added to the reaction mixture. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to obtain compound 80 (19.41 g, yield 71%). Mass spectrometry: MALDI-TOF-MS (m / z) = 546.41 (C, 92.24; H, 7.76).

[0129] Synthesis Example 14: Synthesis of Compound 86

[0130]

[0131] Intermediate A-4 (22.32 g; 50 mmol), 9-phenyl-10-(4-bromophenyl)anthracene (20.47 g; 50 mmol), tris(dibenzylideneacetone)palladium (0.48 g; 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.41 g; 1 mmol), and potassium carbonate K₂CO₃ (10.37 g; 75 mmol) were added to 400 mL of 1,4- In dioxane, the mixture was heated to 108°C under nitrogen protection and stirred for 3 hours. Then, it was cooled to room temperature, and 200 mL of toluene and 200 mL of water were added to the reaction solution. The mixture was separated, and the organic phase was dried over anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to obtain compound 86 (25.63 g, yield 79%). Mass spectrometry: MALDI-TOF-MS (m / z) = 648.67 (C, 92.56; H, 7.44).

[0132] Synthesis Example 15: Synthesis of Compound 98

[0133]

[0134] Intermediate A-4 (22.32 g; 50 mmol), 1-bromo-6-phenyldibenzofuran (16.16 g; 50 mmol), tris(dibenzylideneacetone)palladium (0.48 g; 0.5 mmol), 2-dicyclohexylphosphine-2',6'-dimethoxybiphenyl (0.41 g; 1 mmol), and potassium carbonate K₂CO₃ (10.37 g; 75 mmol) were added to 400 mL of 1,4-dioxane. The mixture was heated to 108°C under nitrogen protection and stirred for 3 hours. Then it was cooled to room temperature, and 200 mL of toluene and 200 mL of water were added to the reaction solution. The mixture was separated, and the organic phase was dried with anhydrous magnesium sulfate. After filtration, the solvent was removed from the filtrate under reduced pressure to obtain compound 97 (21.39 g, yield 76%). Mass spectrometry: MALDI-TOF-MS (m / z) = 562.48 (C, 89.63; H, 7.52; O, 2.85).

[0135] Device fabrication:

[0136] The glass substrate with a 120nm ITO transparent film was ultrasonically cleaned with acetone, isopropanol and deionized water for 10 minutes each, vacuum dried at 105°C for 2 hours, and then UV ozone washed for 15 minutes. The ITO glass substrate was then transferred to a vacuum evaporation machine.

[0137] On the side where the ITO thin film is formed, molybdenum trioxide (MoO3) is vacuum-deposited to form a 10 nm thick hole injection layer.

[0138] On the hole injection layer described above, 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline] (TAPC) is vacuum evaporated to form a hole transport layer with a thickness of 70 nm.

[0139] On the hole transport layer described above, 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA) is vacuum-deposited to form a 10 nm electron blocking layer;

[0140] On the aforementioned electron blocking layer, compound 1 (as the light-emitting host material, 90 wt%) and BCzVBi (as the light-emitting guest material, 10 wt%) prepared in the above-mentioned synthesis example 1 are jointly vacuum-deposited to form a light-emitting layer with a thickness of 30 nm.

[0141] On the aforementioned light-emitting layer, 3,3'-[5'-[3-(3-pyridyl)phenyl][1,1':3',1”-terphenyl]-3,3”-diyl]dipyridine (TmPyPB) is vacuum-deposited to form an electron transport layer with a thickness of 40 nm;

[0142] On the aforementioned electron transport layer, lithium fluoride (LiF) is vacuum-deposited to form an electron injection layer with a thickness of 1 nm.

[0143] Finally, aluminum (Al) is vacuum-deposited onto the aforementioned electron injection layer to form a 100 nm cathode.

[0144] Examples 2 to 14

[0145] Organic electroluminescent devices were prepared using the same method as in Device Example 1, except that the compounds synthesized in Synthesis Examples 2 to 14 were used to replace compound 1 prepared in Synthesis Example 1.

[0146] Comparative Examples 1 to 5

[0147] Except that when forming the light-emitting layer, the mixed components of compounds A, B, C, D, and E shown in the table below are used instead of the mixed components in Example 1, the organic electroluminescent device is fabricated using the same method as in Example 1.

[0148]

[0149] Performance testing:

[0150] The performance of the organic electroluminescent devices prepared in the above-described device embodiments and comparative embodiments was tested, and the experimental results are shown in Table 1 below:

[0151] Table 1

[0152]

[0153]

[0154] As shown in Table 1, the main material of this invention, when used in OLEDs, exhibits significantly improved efficiency and lifetime compared to the comparative method, along with higher color purity. This is primarily due to two reasons: First, this invention utilizes adamantane-substituted deuterated aryl groups at key sites of the main molecule to ensure its stability, while retaining hydrogen substitution in the core unit to maintain sufficient activity for energy transfer, resulting in a substantial performance improvement. Second, this invention introduces hole-transporting units (dibenzofuran or dibenzothiophene) at the other end of the main molecule, which enhances the compound's hole transport performance, stability, and charge transport capabilities, thereby effectively improving device stability and lifetime.

[0155] 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. A deuterated compound, characterized in that... It has the structure shown in Equation 1: R5 is selected from substituted or unsubstituted C. 6-30 aryl, substituted or unsubstituted C 6-30 Aromatic amino groups, substituted or unsubstituted C 6-30 heteroaryl; L1 is selected from direct bond or C 6-30 The deuterated arylene group, L2 is selected from the direct bond or phenylene; L1 is C 6-30 In the case of deuterated aryl groups, R1 to R4 and R6 to R9 may be the same or different from each other, and each may be hydrogen or deuterium independently. When L1 is a direct bond, R1 to R4 and R6 to R9 are selected from deuterium.

2. The deuterated compound according to claim 1, characterized in that... The L1 is selected from deuterated phenylene, deuterated biphenylene, or deuterated fused aryl groups having 2-3 phenyl groups.

3. The deuterated compound according to claim 1, characterized in that, The C 6-30 Heteroaryl groups have at least one C 5-6 heterocyclic rings; The substituted or unsubstituted C 6-30 The aromatic amino group has the following structural formula: *-L3-NR 14 R 15 The L3 is selected from direct bonds or phenylene, and the R 14 R 15 The same or different are selected from aryl or heteroaryl groups having 1-2 phenyl groups; The C 6-30 The aryl group is selected from phenyl or polycyclic aryl groups having 2-4 phenyl groups, wherein the 2-4 phenyl groups are connected by direct bonds, C-terminal bonds, or C-terminal bonds. 1-3 It is connected in any one or more ways, either alkyl or carbon-carbon covalent bonds.

4. The deuterated compound according to claim 1, characterized in that, C 6-30 Heteroaryl groups have the structural formula shown in Formula 2-4: R 10 To R 13 They may be the same as or different from each other, and each is independently H, cyano, halogen, C. 1-5 alkyl, C 6-12 aryl, R 10 To R 13 Any two adjacent elements can combine to form a ring, where X is selected from N-ph, O, N, or S; and Y is independently selected from N, CR, and S. 16 R 16 Y is hydrogen, phenyl, or biphenyl, and 1-3 non-adjacent Ys are N; * is the connection site between Formula 2 and Formula 1.

5. The deuterated compound according to claim 4, characterized in that, The R 10 To R 13 They may be the same as or different from each other, and each is independently H, cyano, halogen, C. 1-5 Alkyl and phenyl groups.

6. The deuterated compound according to claim 4, characterized in that, Formula 4 is selected from: m is selected from 0, 1, or 2, R 16 It is a phenyl group.

7. The deuterated compound according to claim 1, characterized in that, The C 6-30 The aryl group is selected from the group consisting of one or more of the following groups: * indicates the connection point with Equation 1.

8. The deuterated compound according to claim 7, characterized in that, The compound:

9. An organic light-emitting device, comprising a first electrode and a second electrode disposed opposite to it, wherein at least one organic material layer is present between the first electrode and the second electrode, and the organic material layer is at least one layer, characterized in that... At least one layer of the organic material layer comprises the deuterated compound as described in any one of claims 1 to 9.

10. The organic light-emitting device according to claim 9, characterized in that: The organic material layer includes a light-emitting layer, which includes the deuterated compound.

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