Organic Compounds, Their Applications and Organic Electroluminescent Devices

Abstract

The present invention relates to an organic compound, its application and an organic electroluminescent device. The organic compound is represented by Formula I, where X is oxygen or sulfur; R is a heteroaryl group having a nitrogen-containing heterocycle, and the nitrogen-containing heterocycle is selected from one or more of a pyrimidine ring, a quinoxaline ring, a quinazoline ring and a triazine ring; L is selected from absent, arylene and heteroarylene. When the organic electroluminescent compound of the present invention is applied to an organic electroluminescent device, it has a lower driving voltage and higher device luminescence efficiency.

Description

Technical Field

[0001] The present invention relates to the field of organic electroluminescent devices, and particularly to an organic compound, its application, and an organic electroluminescent device. Background Art

[0002] The organic electroluminescent phenomenon was first discovered by Pope et al. in 1963. They found that a single crystal of anthracene could emit weak blue light under the drive of a voltage above 100V. However, due to the high drive voltage and large thickness of the single crystal anthracene, it did not attract wide attention. It was not until 1987 that Dr. Deng Qingyun et al. of Eastman Kodak Company reported two organic semiconductor materials, aluminum 8-hydroxyquinoline with high fluorescence efficiency and good electron transport properties and aromatic diamine with good hole transport properties. A double-layer organic electroluminescent device (Organic Light-Emitting Diodes, OLED) was prepared by vacuum thermal evaporation. Under a drive voltage of less than 10V, the external quantum efficiency of the aforementioned OLED reached 1%, and the brightness was as high as 1000 Cd / m2, setting off a research boom in OLEDs and promoting further research on organic electroluminescent materials.

[0003] In recent years, as a new generation of display technology, OLEDs have gradually come into people's view. Their broad application prospects and rapid technological progress have made OLEDs one of the hottest research topics in the display field and scientific research product development.

[0004] Currently, OLEDs or screens still have the defects of high drive voltage and low current efficiency. To improve these defects, on the one hand, the device structure and manufacturing process need to be further optimized, and on the other hand, the performance of the materials of each functional layer also needs to be improved.

[0005] The electron migration ability and exciton blocking ability of electron transport materials play a crucial role in the drive voltage and luminous efficiency of devices. Therefore, the market urgently needs to develop high-performance electron transport materials to reduce the drive voltage of devices and improve the luminous efficiency of devices. Summary of the Invention

[0006] The purpose of the present invention is to overcome the defects of high drive voltage and low luminous efficiency of OLEDs provided by the prior art.

[0007] To this end, in the first aspect, the present application provides an organic compound as shown in Formula I

[0008]

[0009] Wherein, X is oxygen or sulfur; R is a heteroaryl having a nitrogen heterocycle, and the nitrogen-containing heterocycle is selected from one or more of a pyrimidine ring, a quinoxaline ring, a quinazoline ring, and a triazine ring; L is selected from absent, arylene, and heteroarylene.

[0010] According to an embodiment of the present invention, R is a C3-C40 heteroaryl group, and L is selected from absent, a C6-C20 arylene group, and a C3-C20 heteroarylene group. In some embodiments, L is absent, that is, R is directly bonded to the ring. In some embodiments, L is selected from a C6-C20 arylene group and a C3-C20 heteroarylene group. According to an embodiment of the present invention, L is selected from a phenylene group, a naphthylene group, an anthrylene group, a phenanthrylene group, a biphenylene group, a dibenzothiophene group, and a dibenzofuran group.

[0011] According to an embodiment of the present invention, R is selected from the following groups:

[0012]

[0013] wherein Ar1 and Ar2 are each independently selected from an aryl group and a heteroaryl group.

[0014] According to an embodiment of the present invention, Ar1 and Ar2 are each independently selected from a C6-C20 aryl group and a C3-C40 heteroaryl group.

[0015] According to an embodiment of the present invention, Ar1 and Ar2 are each independently selected from a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, a dibenzofuran group, a dibenzothiophene group, a phenyl-substituted naphthyl group, a phenyl-substituted anthryl group, a phenyl-substituted biphenyl group, a phenyl-substituted dibenzofuran group, a phenyl-substituted dibenzothiophene group, a naphthyl-substituted phenyl group, a naphthyl-substituted naphthyl group, a naphthyl-substituted anthryl group, a naphthyl-substituted biphenyl group, a naphthyl-substituted dibenzofuran group, and a naphthyl-substituted dibenzothiophene group.

[0016] According to an embodiment of the present invention, the organic compound is selected from the following compounds:

[0017]

[0018]

[0019]

[0020] In a second aspect, the present invention provides an application of the organic compound shown in Formula I above in an organic electroluminescent device. According to an embodiment of the present invention, in the organic electroluminescent device, the organic compound is used as an electron transport material.

[0021] In a third aspect, the present invention provides an organic electroluminescent device, which includes an electron transport layer, and the electron transport layer contains the organic compound shown in Formula I described above.

[0022] According to some embodiments of the present invention, the organic electroluminescent device of the present invention further includes an anode, a hole injection layer, a hole transport layer, an optional electron blocking layer, a light-emitting layer, an optional hole blocking layer, an electron injection layer, and a cathode.

[0023] According to some embodiments of the present invention, the anode material for forming the anode generally preferably has a large work function. For example, the anode materials used in the present invention are selected from one or more of the following materials: metals such as vanadium, chromium, copper, and gold, or other alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide, indium zinc oxide, and tin dioxide; combinations of metals and oxides such as zinc oxide:aluminum, but not limited thereto.

[0024] According to some embodiments of the present invention, the material for forming the hole injection layer has the ability to transport holes. Therefore, the material of the hole injection layer has the effect of injecting holes into the anode, has an excellent hole injection effect on the light-emitting layer or the light-emitting material, prevents excitons generated in the light-emitting layer from moving to the electron injection layer or the electron injection material, and in addition, has excellent thin film forming ability. The HOMO of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.

[0025] According to some embodiments of the present invention, the hole injection material and the hole transport material include at least one of aromatic amine derivatives (such as NPB, SqMA1), hexaazatriphenylene derivatives (such as HACTN), indolocarbazole derivatives, conductive polymers (such as PEDOT / PSS), phthalocyanine or porphyrin derivatives, dibenzindenofluoreneamine, spirobifluoreneamine, but not limited thereto.

[0026] According to some embodiments of the present invention, the hole injection layer and the hole transport layer can be formed, for example, of aromatic amine derivatives having the following general formula:

[0027]

[0028] The groups of R1 to R9 in the above general formula are each independently selected from a single bond, hydrogen, deuterium, alkyl, benzene, biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, benzophenanthrene, pyrene, fluorene, dimethylfluorene, spirobifluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolocarbazole, indenoindolocarbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine, or triazine.

[0029] According to some embodiments of the present invention, the material for forming the electron blocking layer is not particularly limited. Generally, compounds that can meet the following first and / or second conditions can be considered for use:

[0030] No. 1: It has a relatively shallow LUMO energy level (smaller absolute value), and the purpose is to reduce the number of electrons leaving the light-emitting layer, thereby increasing the recombination probability of electrons and holes in the light-emitting layer.

[0031] No. 2: It has a relatively large triplet energy, and the purpose is to reduce the number of excitons leaving the light-emitting layer, thereby increasing the efficiency of exciton conversion to light emission.

[0032] According to some embodiments of the present invention, the materials for forming the electron blocking layer include, but are not limited to, aromatic amine derivatives (such as NPB), spirobifluorene amines (such as SpMA2), and some of the electron blocking materials have similar structures to the hole injection materials and hole transport materials.

[0033] According to some embodiments of the present invention, when the light-emitting material of the light-emitting layer is a material that can emit light in the visible light region by receiving holes and electrons from the hole transport layer and the electron transport layer respectively and combining the holes and electrons, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence.

[0034] According to some embodiments of the present invention, the light-emitting layer may include a host material and a guest material. According to some embodiments of the present invention, the host material of the device contains the compound described in the first aspect of the present invention. According to some embodiments of the present invention, the guest material is preferably a compound that emits light through at least one of phosphorescence, fluorescence, TADF (thermally activated delayed fluorescence), MLCT (metal-to-ligand charge transfer), HLCT (having a hybrid CT state), and triplet-triplet annihilation methods.

[0035] According to some embodiments of the present invention, the guest material in the light-emitting layer may include derivatives of perylene, derivatives of anthracene, fluorene derivatives, stilbenyl aryl derivatives, arylamine derivatives, organosilicon derivatives, organoboron derivatives, carbazole-triazine derivatives, acridine derivatives, derivatives containing ketones, sulfone group derivatives, cyano derivatives, and xanthene derivatives, but are not limited thereto.

[0036] In some preferred embodiments of the present invention, the sulfone group derivatives have the following general formula:

[0037]

[0038] The ketone derivatives have the following general formula:

[0039]

[0040] In the general formulas of the above-mentioned sulfone-based derivatives and ketone-based derivatives, R20, R21, R22 and R23 are each independently selected from a single bond, hydrogen, deuterium, alkyl, benzene, biphenyl, terphenyl, quaterphenyl, naphthalene, phenylnaphthalene, anthracene, phenanthrene, benzophenanthrene, pyrene, fluorene, carbazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, indole, indolocarbazole, indeno-carbazole, pyridine, pyrimidine, imidazole, thiazole, quinoline, isoquinoline, quinoxaline, quinazoline, porphyrin, carboline, pyrazine, pyridazine or triazine, and groups represented by their substituents.

[0041] According to some embodiments of the present invention, the material of the hole blocking layer may also preferably be a compound having the following first and / or second conditions:

[0042] First: having a relatively deep HOMO energy level (larger absolute value), the purpose of which is to reduce the number of holes leaving the light-emitting layer, thereby increasing the recombination probability of electrons and holes in the light-emitting layer.

[0043] Second: having a relatively large triplet energy, the purpose of which is to reduce the number of excitons leaving the light-emitting layer, thereby increasing the efficiency of exciton conversion to light emission.

[0044] According to some embodiments of the present invention, the material for forming the hole blocking layer may include, for example, but not limited to, compounds containing phenanthroline derivatives (such as Bphen, BCP), benzophenanthrene derivatives, and benzimidazole derivatives.

[0045] According to some embodiments of the present invention, the electron injection layer is a layer that injects electrons from the electrode, and the electron injection material is preferably a compound with the following properties: it has the ability to transport electrons, has the effect of injecting electrons from the cathode, has an excellent effect of injecting electrons into the light-emitting layer or light-emitting material, prevents excitons generated in the light-emitting layer from moving to the hole injection layer, and also has excellent thin film forming ability. The electron injection layer materials include, for example, but not limited to, LiF, CsF, Cs2CO3, LiQ.

[0046] According to some embodiments of the present invention, the cathode material formed is generally preferably a material with a small work function, which can smoothly inject electrons into the organic material layer. The cathode materials that can be used in the present disclosure can be selected from one or more of the following materials: one or more of Al, Mg, and Ag.

[0047] The present invention has at least the following specific advantages:

[0048] 1. The compound provided by the present invention has appropriate HOMO and LUMO energy levels, can match with adjacent materials, reduce the injection barrier, and at the same time can prevent leakage. When the compound of the present invention is applied to an organic electroluminescent device, it can effectively reduce the driving voltage of the device.

[0049] 2. The compounds of the present invention have excellent electron mobility and can increase the recombination probability of electrons and holes. When applied to organic electroluminescent devices, they can increase the luminous efficiency of the devices.

[0050] 3. The mother nucleus of the present invention contains an oxazole or thiazole structure, and O / S is located at the 1-position, which can weaken the intermolecular interaction, avoid intermolecular aggregation, thereby improving the film-forming property of the compound and increasing the service life of the material. Detailed implementation manners

[0051] The present invention does not particularly limit the specific method for preparing the aforementioned compounds. Those skilled in the art can obtain the aforementioned compounds of the present invention according to the specific structural formulas provided by the present invention in combination with the conventional process routes in the field of organic synthesis. Moreover, several examples are exemplarily listed in the following text of the present invention to illustrate the preparation methods of the compounds of the present invention. Those skilled in the art can also obtain the specific preparation methods of all the remaining compounds by replacing the types of raw materials according to the preparation methods of the compounds in the following text of the present invention. The present invention will not elaborate on the preparation methods of all the compounds, and those skilled in the art should not understand it as a limitation to the present invention.

[0052] The present invention will be described in detail below through examples. In the following examples, unless otherwise specified, various raw materials used are ordinary commercially available products. Unless otherwise specified, the room temperature mentioned below means 25 ± 1°C.

[0053] Preparation Example 1:

[0054]

[0055] Synthesis of Intermediate A: In a 500 ml three-necked flask, bromobenzene (58 mmol) was added to anhydrous THF (100 ml) and stirred. Under nitrogen protection, the temperature was lowered to -78°C, and 2.5 mol / L n-butyllithium (25.5 ml) was added dropwise. It was kept at -78°C for 1 hour, and 4-formyl oxazole (58 mmol) was added at -78°C. Then the temperature was raised to room temperature, and the reaction was completed after 1 hour. The reaction was quenched with saturated ammonium chloride aqueous solution and extracted three times with chloroform. The organic phase was dried over anhydrous sodium sulfate and then filtered to remove the desiccant to obtain a filtrate, which was concentrated by rotary evaporation to obtain a crude product. The crude product was purified by column chromatography to obtain white solid A (yield: 72.5%).

[0056] Synthesis of Intermediate B: The synthesis method was the same as that of Intermediate A, and white solid B was obtained (yield: 69.3%).

[0057] Synthesis of Intermediate C: Intermediate A (39 mmol) was added to dichloromethane (70 ml) and stirred. Br2 (39 mmol) was added dropwise at room temperature. After the addition was completed, the reaction was allowed to proceed overnight at room temperature. After detecting that the raw materials had reacted completely, water (150 ml) was added dropwise to the reaction solution, and the mixture was extracted three times with dichloromethane. The residue obtained by filtration was purified by column chromatography to obtain white solid C (yield: 45.2%).

[0058] Synthesis of Intermediate D: The synthesis method was the same as that of Intermediate C, and white solid D was obtained (yield: 48.8%).

[0059] Synthesis of Intermediate E: In a 500-ml three-necked flask, Intermediate C (25 mmol) was added to trichloroethane (65 ml) and stirred until dissolved. Pyridinium chlorochromate (25 mmol) was added, and the temperature was raised to reflux. After reacting for 10 hours, TLC monitoring showed that the reaction was basically complete. The mixture was cooled to room temperature, filtered by suction to obtain the organic phase, concentrated under reduced pressure, and purified by column chromatography to obtain white solid E (yield: 79.4%).

[0060] Synthesis of Intermediate F: The synthesis method was the same as that of Intermediate E, and white solid F was obtained (yield: 78.7%).

[0061] Synthesis of Intermediate G: Intermediate E (0.043 mol) was added to DMAC solvent (140 ml) and stirred until dissolved. Copper powder (0.129 mol) was added, and the mixture was heated and stirred. The temperature was raised to reflux, and after reacting for 24 hours, TLC monitoring showed that the reaction was basically complete. The mixture was cooled to room temperature, and a mixture of water (50 ml) and ether (100 ml) was added for extraction to obtain the organic phase. The organic phase was concentrated under reduced pressure and purified by column chromatography to obtain white solid G (yield: 79%).

[0062] Synthesis of Intermediate H: The synthesis method was the same as that of Intermediate G, and white solid H was obtained (yield: 78.2%).

[0063] Synthesis of Intermediate I: In a 500 ml three-necked flask, add o-bromobiphenyl (36 mmol) to anhydrous THF (60 ml). Under nitrogen protection, cool the temperature to -78 °C, dropwise add 2.5 M n-butyllithium (15.8 ml), keep the temperature at -78 °C for 1 hour, add Intermediate G (36 mmol) at -78 °C, keep for 1 hour after addition, then warm up to room temperature. After 1 h, the reaction is completed. Quench with water, extract the organic phase three times with chloroform, filter the desiccant after drying with anhydrous sodium sulfate to obtain the filtrate, rotary evaporate to obtain the crude product. Dissolve the crude product in 1,2-dichloroethane (100 ml), cool the temperature to 0 °C, dropwise add trifluoromethanesulfonic acid (3.6 mol). After the addition is complete, heat under reflux for 2 hours, cool to room temperature, adjust the solution to neutral with aqueous NaHCO3 solution, dry the organic phase with anhydrous sodium sulfate and then rotary evaporate under reduced pressure. Obtain white solid I by column chromatography (Yield: 63.2%).

[0064] Synthesis of Intermediate J: The synthesis method is the same as that of Intermediate I, and white solid J is obtained (Yield: 64.4%).

[0065] Synthesis of Intermediate K: The synthesis method is the same as that of Intermediate C, and white solid K is obtained (Yield: 47.9%).

[0066] Mass spectrometry: C22H12INO, theoretical value: 433.00, measured value: 433.0.

[0067] Elemental analysis: Theoretical value: C: 60.99%, H: 2.79%, N: 3.23%; Measured value: C: 60.97%, H: 2.83%, N: 3.22%.

[0068] Synthesis of Intermediate L: The synthesis method is the same as that of Intermediate C, and white solid L is obtained (Yield: 47.7%).

[0069] Mass spectrometry: C22H12INS, theoretical value: 448.97, measured value: 449.0.

[0070] Elemental analysis: Theoretical value: C: 58.81%, H: 2.69%, N: 3.12%; Measured value: C: 58.84%, H: 2.67%, N: 3.15%.

[0071] Preparation Example 2:

[0072]

[0073] Synthesis of Intermediate 1-1: In a 500 ml three-necked flask, under nitrogen protection, successively add 1,4-dioxane solvent (165 ml), 2-chloro-4,6-diphenyl-1,3,5-triazine (0.062 mol), bis(pinacolato)diboron (0.062 mol), potassium acetate (0.16 mol) and dichlorobis(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) (0.62 mmol) while stirring. Heat up to reflux for 4 h. After detecting the complete reaction of the raw materials by HPLC, cool the reaction solution to room temperature and then rotary evaporate the reaction solution under reduced pressure to obtain the crude product. Dissolve the crude product in toluene solvent, heat and stir, heat up to reflux, and decolorize through a silica gel column. Rotary evaporate the filtrate under reduced pressure until there is a small amount of solvent left, then add ethanol (250 ml) for pulping, and recrystallize with toluene / ethanol to obtain a white solid (yield: 53.2%).

[0074] Synthesis of Compound 1: In a 500 ml three-necked flask, under nitrogen protection, add Intermediate 1-1 (0.055 mol), Intermediate K (0.055 mol), toluene (240 ml), ethanol (50 ml), PdCl2(dppf)3 (0.55 mmol), and 20 ml of an aqueous solution containing potassium carbonate (0.138 mol). Start stirring and heat to 90 °C for overnight reaction. After 20 h, cool the reaction to 40 °C, filter to obtain the crude product, wash the crude product with water (360 ml), and then wash with methanol (360 ml) to obtain a gray solid. Separate the pale yellow solid compound 1 by silica gel column chromatography (yield: 86.4%).

[0075] Mass spectrometry: C37H22N4O, theoretical value: 538.18, measured value: 538.2. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 7.20 - 7.25 (1H, m), 7.27 - 7.28 (1H, m), 7.31 - 7.46 (5H, m), 7.47 - 7.53 (6H, m), 7.72 - 7.78 (1H, m), 7.88 - 7.92 (2H, m), 8.06 - 8.10 (2H, m), 8.33 - 8.40 (4H, m).

[0076] Preparation Example 3:

[0077]

[0078] Synthesis of Intermediate 6-1: The synthesis method is the same as that of Intermediate 1-1, and Intermediate 6-1 is obtained (yield: 58.6%).

[0079] Synthesis of Compound 6: The synthesis method is the same as that of Compound 1, and Compound 1 is obtained (yield: 85.3%).

[0080] Mass spectrometry: C49H30N4O, theoretical value: 690.24, measured value: 690.3. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 7.20 - 7.24 (1H, m), 7.26 - 7.27 (1H, m), 7.30 - 7.45 (5H, m), 7.46 - 7.53 (6H, m), 7.57 - 7.63 (2H, m), 7.66 - 7.78 (3H, m), 7.86 - 7.92 (4H, m), 8.11 - 8.17 (2H, m), 8.32 - 8.44 (6H, m).

[0081] Preparation Example 4:

[0082]

[0083] Synthesis of Intermediate 14-1: The synthesis method is the same as that of Intermediate 1-1, and Intermediate 14-1 is obtained (yield: 50.6%).

[0084] Synthesis of Compound 14: The synthesis method is the same as that of Compound 1, and Compound 14 is obtained (yield: 83.5%).

[0085] Mass spectrometry: C43H24N4O2, theoretical value: 628.19, measured value: 628.2. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 7.20 - 7.25 (1H, m), 7.26 - 7.28 (1H, m), 7.30 - 7.46 (7H, m), 7.47 - 7.59 (5H, m), 7.74 - 7.80 (2H, m), 7.88 - 8.00 (5H, m), 8.20 - 8.22 (1H, m) 8.32 - 8.44 (2H, m).

[0086] Preparation Example 5:

[0087]

[0088] Synthesis of Intermediate 33-1: The synthesis method is the same as that of Intermediate 1-1, and Intermediate 33-1 is obtained (yield: 53.7%).

[0089] Synthesis of Compound 33: The synthesis method is the same as that of Compound 1, and Compound 33 is obtained (yield: 84.7%).

[0090] Mass spectrometry: C36H21N3O, theoretical value: 511.17, measured value: 511.2. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 7.20 - 7.25 (1H, m), 7.27 - 7.35 (2H, m), 7.36 - 7.53 (5H, m), 7.54 - 7.69 (3H, m), 7.74 - 7.83 (4H, m), 7.88 - 7.94 (4H, m), 7.97 - 8.02 (1H, m), 8.11 - 8.15 (1H, m).

[0091] Preparation Example 6:

[0092]

[0093] Synthesis of Compound 46: In a 500 ml three-necked flask, under nitrogen protection, [4-(4,6-diphenyl-1,3,5-triazin-2-yl)phenyl]boronic acid (0.047 mol), Intermediate L (0.047 mol), and a mixed solution of toluene, ethanol, and water (mixed in a ratio of 3:2:1) (170 ml) were added in sequence, and stirring was started. Then, potassium carbonate (0.118 mol) and tetrakis(triphenylphosphine)palladium (0.47 mmol) were added in sequence. The temperature was raised to reflux for 6 h. When HPLC detected that the raw materials had basically reacted, deionized water (250 ml) was added to the reaction solution, and stirring was carried out for 10 min. The organic phase was taken and dried over anhydrous magnesium sulfate. The desiccant was filtered, the organic solvent was evaporated, and the residue was separated by silica gel column chromatography to obtain a white solid (yield: 68.7%).

[0094] Mass spectrometry: C43H26N4S, theoretical value: 630.19, measured value: 630.2. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 7.20 - 7.24 (1H, m), 7.26 - 7.28 (1H, m), 7.30 - 7.46 (5H, m), 7.47 - 7.53 (6H, m), 7.73 - 7.78 (1H, m), 7.87 - 7.93 (4H, m), 7.94 - 7.98 (4H, m), 8.32 - 8.40 (4H, m).

[0095] Preparation Example 7:

[0096] Synthesis of Intermediate 53-1: The synthesis method was the same as that of Intermediate 1-1, and Intermediate 53-1 was obtained (yield: 52.1%).

[0097] Synthesis of Compound 53: The synthesis method was the same as that of Compound 1, and Compound 53 was obtained (yield: 83.5%).

[0098] Mass spectrometry: C43H26N4S, theoretical value: 630.19, measured value: 630.2. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 7.22 - 7.26 (4H, m), 7.32 - 7.44 (6H, m), 7.47 - 7.52 (5H, m), 7.73 - 7.77 (3H, m), 7.89 - 7.91 (2H, m), 7.94 - 7.98 (4H, m), 8.34 - 8.38 (2H, m).

[0099] Preparation Example 8:

[0100]

[0101] Synthesis of Intermediate 67-1: The synthesis method is the same as that of Intermediate 1-1, and Intermediate 67-1 is obtained (yield: 54.6%).

[0102] Synthesis of Intermediate 67-2: The synthesis method is the same as that of Compound 1, and Intermediate 67-2 is obtained (yield: 82.4%).

[0103] Synthesis of Intermediate 67-3: The synthesis method is the same as that of Intermediate 1-1, and Intermediate 67-3 is obtained (yield: 73.1%).

[0104] Synthesis of Compound 67: The synthesis method is the same as that of Compound 1, and Compound 67 is obtained (yield: 83.5%).

[0105] Mass spectrometry: C48H29N3S, theoretical value: 679.21, measured value: 679.2. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 7.20 - 7.25 (1H, m), 7.26 - 7.28 (1H, m), 7.31 - 7.44 (5H, m), 7.45 - 7.59 (8H, m), 7.72 - 7.78 (1H, m), 7.85 - 7.96 (6H, m), 7.99 - 8.02 (2H, m), 8.22 - 8.24 (1H, m), 8.31 - 8.39 (2H, m), 8.93 - 9.01 (2H, m).

[0106] Preparation Example 9:

[0107]

[0108] Synthesis of Intermediate 86-1: The synthesis method is the same as that of Intermediate 1-1, and Intermediate 86-1 is obtained (yield: 52.8%).

[0109] Synthesis of Intermediate 86-2: The synthesis method is the same as that of Compound 1, and Intermediate 67-2 is obtained (yield: 83.3%).

[0110] Synthesis of Intermediate 86-3: The synthesis method is the same as that of Intermediate 1-1, and Intermediate 67-3 is obtained (yield: 78.6%).

[0111] Synthesis of Compound 86: The synthesis method is the same as that of Compound 1, and Compound 67 is obtained (yield: 82.2%).

[0112] Mass spectrometry: C42H25N3S, theoretical value: 603.18, measured value: 603.2. 1H-NMR (400 MHz, CDCl3) (ppm) δ = 7.20 - 7.25 (1H, m), 7.26 - 7.28 (1H, m), 7.29 - 7.35 (4H, m), 7.36 - 7.46 (3H, m), 7.55 - 7.70 (3H, m), 7.74 - 7.83 (3H, m), 7.88 - 8.06 (8H, m), 8.84 - 8.89 (2H, m).

[0113] Device Example 1

[0114] The glass plate coated with the ITO transparent conductive layer is ultrasonically treated in a commercial cleaning agent, rinsed in deionized water, ultrasonically degreased in a mixed solvent of acetone:ethanol (volume ratio 1:1), baked in a clean environment until all water is removed, cleaned with ultraviolet light and ozone, and bombarded with a low-energy cation beam on the surface;

[0115] Place the glass substrate with the anode above in a vacuum chamber, evacuate to 1×10 -5 Pa, vacuum deposit HAT-CN as the hole injection layer on the above anode layer film, the deposition rate is 0.1 nm / s, and the total film thickness is 1 nm; then deposit the hole transport layer NPB, the deposition rate is 0.1 nm / s, and the thickness is 60 nm;

[0116] Vacuum deposit the electron blocking layer TCTA of the device on the hole transport layer, the deposition rate is 0.1 nm / s, and the total film thickness is 10 nm;

[0117] Vacuum deposit the light-emitting layer of the device on the electron blocking layer. The light-emitting layer includes a host material and a guest material. Using the method of co-evaporation from multiple sources, adjust the deposition rate of the host material DIC-TRZ to 0.1 nm / s, and set the deposition rate of the guest material Ir(ppy)3 at a 10% ratio. The total film thickness is 30 nm;

[0118] The electron transport layer of the device is vacuum-evaporated above the light-emitting layer. By using the method of co-evaporation from multiple sources, the evaporation rates of both ET-1 and Compound 1 are adjusted to be 0.1 nm / s, and the total film thickness of the evaporation is 30 nm;

[0119] A 0.5-nm-thick LiF is vacuum-evaporated as the electron injection layer on the electron transport layer (ETL), and a 150-nm-thick Al layer is used as the cathode of the device.

[0120] The molecular structures involved are as follows:

[0121]

[0122] Device Examples 2-8

[0123] Organic electroluminescent devices of Device Examples 2-8 are prepared by a method similar to that of Device Example 1. The difference is that Compound 1 in Device Example 1 is replaced with the compounds shown in Table 1.

[0124] Device Comparative Examples 1-2

[0125] Organic electroluminescent devices of Device Comparative Examples 1-2 are prepared by a method similar to that of Device Example 1. The difference is that Compound 1 in Device Example 1 is replaced with the following compounds Ref-1 and Ref-2, respectively.

[0126]

[0127] Test Example 1

[0128] At a brightness of 10000 cd / m 2 The driving voltages and current efficiencies of the organic electroluminescent devices prepared in Device Examples 1-8 and Device Comparative Examples 1-2 are measured, and the results are shown in Table 1.

[0129] Table 1

[0130]

[0131]

[0132] The above results show that, compared with the comparative examples, the organic compounds of the present invention have a lower driving voltage and a higher device luminescence efficiency when applied to organic electroluminescent devices.

[0133] The preferred embodiments of the present invention have been described in detail above. However, the present invention is not limited thereto. Within the scope of the technical concept of the present invention, various simple modifications can be made to the technical solutions of the present invention, including any other suitable combination of each technical feature. These simple modifications and combinations should also be regarded as the content disclosed by the present invention and fall within the protection scope of the present invention.

Claims

1. An organic compound is shown in Formula I: X is oxygen or sulfur; L is selected from absent, C6-C20 arylene, and C3-C20 heteroarylene; R is selected from the following groups: Wherein, Ar1 and Ar2 are each independently selected from phenyl, naphthyl, anthryl, biphenyl, dibenzofuranyl, dibenzothiophenyl, phenyl-substituted naphthyl, phenyl-substituted anthryl, phenyl-substituted biphenyl, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, naphthyl-substituted phenyl, naphthyl-substituted naphthyl, naphthyl-substituted anthryl, naphthyl-substituted biphenyl, naphthyl-substituted dibenzofuranyl, naphthyl-substituted dibenzothiophenyl.

2. The organic compound according to claim 1, wherein, L is selected from C6-C20 arylene and C3-C20 heteroarylene.

3. The organic compound according to claim 1, wherein, L is selected from phenylene, naphthylene, anthrylene, phenanthrylene, biphenylene, dibenzothiophene and dibenzofuranyl.

4. An organic compound, wherein, The organic compound is selected from the following compounds:

5. Use of the organic compound according to any one of claims 1-4 in an organic electroluminescent device.

6. The use according to claim 5, wherein, The organic compound is used as an electron transport material.

7. An organic electroluminescent device includes an electron transport layer, and the electron transport layer includes the organic compound according to any one of claims 1-4.

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