An organic compound and use thereof

Abstract

The application provides an organic compound and application thereof, in particular provides an organic compound, an OLED display panel and an electronic device, the organic compound has a structure shown in formula (I); the OLED display panel comprises a first electrode, a second electrode and an organic thin film layer arranged between the first electrode and the second electrode; the organic thin film layer comprises an emitting layer; a host material of the emitting layer comprises any one or a combination of at least two of the organic compounds; the electronic device comprises the OLED display panel; when the compound is used as the host material of the emitting layer for preparing an OLED device, the driving voltage of the device can be reduced, and the light emitting efficiency and the service life of the device are improved.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescent materials technology, and relates to an organic compound and its applications, specifically to an organic compound, an OLED display panel, and electronic devices. Background Technology

[0002] 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 production 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] Based on their luminescence mechanism, phosphorescence can be classified into two types: electrofluorescence and electrophosphorescence. Fluorescence is the light emitted when a singlet exciton undergoes a radiative decay transition, while phosphorescence is the light emitted when a triplet exciton radiatively decays to its ground state. According to spin quantum statistics theory, the probability ratio of singlet to triplet exciton formation is 1:3. Fluorescent materials are limited by an internal quantum efficiency of no more than 25%, and their external quantum efficiency is generally below 5%. Electrophosphorescent materials, on the other hand, can theoretically achieve an internal quantum efficiency of 100% and an external quantum efficiency of up to 20%. In 1998, Professor Ma Yuguang of Jilin University in my country and Professor Forrest of Princeton University in the United States reported the first successful observation and explanation of phosphorescent electroluminescence by using osmium complexes and platinum complexes as dyes doped into the luminescent layer. They also pioneered the application of the prepared phosphorescent materials in electroluminescent devices.

[0004] Because phosphorescent heavy metal materials have a long lifetime (μs), high current densities can lead to triplet-triplet annihilation and concentration quenching, causing device performance degradation. Therefore, heavy metal phosphorescent materials are often doped into suitable host materials to form a host-guest doping system, optimizing energy transfer and maximizing luminous efficiency and lifetime. In the current research landscape, commercially viable heavy metal doped materials are mature, making it difficult to develop alternative doping materials. Therefore, focusing on the development of phosphorescent host materials is a common approach among researchers.

[0005] However, existing light-emitting host materials suffer from problems such as insufficient lifetime, low efficiency, and relatively high driving voltage.

[0006] Therefore, in this field, there is a desire to develop a series of new, high-performance light-emitting host materials for use in OLED devices, which can improve the efficiency and lifespan of OLED devices and reduce the driving voltage. Summary of the Invention

[0007] To address the shortcomings of existing technologies, the present invention aims to provide an organic compound and its applications, specifically an organic compound, an OLED display panel, and an electronic device.

[0008] To achieve this objective, the present invention employs the following technical solution: In a first aspect, the present invention provides an organic compound having the structure shown in formula (I): Formula (I) In formula (I), L m Each of them is independently selected from any one of single-bonded, substituted or unsubstituted C6-C40 arylene, or substituted or unsubstituted C5-C40 heteroarylene; In equation (I), n is an integer from 1 to 4, and m is an integer from 1 to n; In equation (I), R i Each of them is independently selected from any one of the following: substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 heteroaryl, substituted or unsubstituted C6-C60 fused-ring aryl, or substituted or unsubstituted C6-C30 arylamine. In equation (I), j is an integer from 1 to 4, and i is an integer from 1 to j; furthermore, j and n have the same value. In formula (I), X is selected from N or CR. c Among them, R c Selected from H or An asterisk (*) indicates a connection point. In equation (I), p is an integer from 0 to 5; In equation (I), dashed lines represent non-existent or single bonds; The substituents are selected from any one of C1-C10 alkyl, C3-C10 cycloalkyl, C1-C6 alkoxy, C6-C60 aryl, and C6-C60 heteroaryl.

[0009] In a second aspect, the present invention provides an OLED display panel, the OLED display panel comprising a first electrode, a second electrode, and an organic thin film layer disposed between the first electrode and the second electrode; the organic thin film layer comprising a light-emitting layer; the main material of the light-emitting layer comprising any one or a combination of at least two of the organic compounds described in the first aspect.

[0010] Thirdly, the present invention provides an electronic device, the electronic device comprising the OLED display panel described in the second aspect.

[0011] Compared with the prior art, the present invention has the following beneficial effects: The organic compound provided by this invention contains acceptor and donor groups in its backbone, which are connected by benzene rings to form a D-Π-A configuration. It has bipolar transport capability. The benzene ring in the middle of the backbone can reduce the planarity of the molecule and increase its rigidity. It has a high glass transition temperature and thermal stability, and can easily form good amorphous thin films. When used as the main material of the light-emitting layer in OLED devices, it can reduce the driving voltage of the device and improve the luminous efficiency and lifetime of the device. Attached Figure Description

[0012] Figure 1 This is a schematic diagram of the structure of an OLED device provided in a specific embodiment of the present invention; Among them, 1-substrate, 2-ITO anode, 3-first hole transport layer, 4-second hole transport layer, 5-electron blocking layer, 6-light emitting layer, 7-first electron transport layer, 8-second electron transport layer, 9-cathode, and 10-capping layer. Detailed Implementation

[0013] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0014] In a first aspect, the present invention provides an organic compound having the structure shown in formula (I): Formula (I) In formula (I), L m Each of these components is independently selected from any one of the following: single-bonded, substituted or unsubstituted aryl groups of C6-C40 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, etc.); and substituted or unsubstituted heteroaryl groups of C5-C40 (e.g., C5, C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, etc.). In equation (I), n is an integer from 1 to 4 (e.g., 1, 2, 3 or 4), and m is an integer from 1 to n; In equation (I), R iEach is independently selected from aryl groups of substituted or unsubstituted C6-C60 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.) or substituted or unsubstituted C6-C60 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48). Any one of the following: heteroaryl groups of C50, C52, C54, C56, C58, C60, etc.; substituted or unsubstituted fused-ring aryl groups of C6-C60 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.); and substituted or unsubstituted aromatic amino groups of C6-C30 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, etc.). In equation (I), j is an integer from 1 to 4 (e.g., 1, 2, 3 or 4), and i is an integer from 1 to j; furthermore, j and n have the same value. In formula (I), X is selected from N or CR. c Among them, R c Selected from H or An asterisk (*) indicates a connection point. In equation (I), p is an integer from 0 to 5 (e.g., 0, 1, 2, 3, 4 or 5); In equation (I), dashed lines represent non-existent or single bonds; The substituents are selected from alkyl groups of C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10), cycloalkyl groups of C3-C10 (e.g., C3, C4, C5, C6, C7, C8, C9, C10), alkoxy groups of C1-C6 (e.g., C1, C2, C3, C4, C5, C6), and C6-C60 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C3...). 4. Any one of the following: aryl groups of C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.; or heteroaryl groups of C6-C60 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, C32, C34, C36, C38, C40, C42, C44, C46, ​​C48, C50, C52, C54, C56, C58, C60, etc.). In this invention, the term "substituent" is explained as follows: when the "substituted or unsubstituted" group is a substituted group, the substituent on the group is called the "substituent." The range of substituent types is as described above, and the same expression applies below. For example, when R... i When the group is selected from an alkyl-substituted aryl group, the alkyl group on the aryl group is the "substituted substituent".

[0015] The organic compound provided by this invention contains acceptor and donor groups in its backbone, which are connected by benzene rings to form a D-Π-A configuration. It has bipolar transport capability. The benzene ring in the middle of the backbone can reduce the planarity of the molecule and increase its rigidity. It has a high glass transition temperature and thermal stability, and can easily form good amorphous thin films. When used as the main material of the light-emitting layer in OLED devices, it can reduce the driving voltage of the device and improve the luminous efficiency and lifetime of the device.

[0016] In one implementation, the L m Each of them is independently selected from any one of single bonds, phenylene, biphenylene, naphthylene, anthraceneylene, and phenanthrene.

[0017] In one implementation, the L m Each of them is independently selected from any one of single bonds, phenylene, and biphenylene.

[0018] In one implementation, the L m Each is independently selected from a single bond or any of the following groups: In this context, the asterisk (*) indicates a connection point.

[0019] In one implementation, the L m Each is independently selected from a single bond or any of the following groups: In this context, the asterisk (*) indicates a connection point.

[0020] In this invention, L m The preferred structure can reduce the planarity of the molecule and increase the rigidity of the organic compound.

[0021] In one implementation, n is an integer from 1 to 3.

[0022] In one implementation, the R i Each of them is independently selected from any one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted 9,10-benzophenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted carbazole, and substituted or unsubstituted aromatic amino groups; The substituents are selected from any one of C1-C10 alkyl, C3-C10 cycloalkyl, C1-C6 alkoxy, C6-C60 aryl, and C6-C60 heteroaryl.

[0023] In one implementation, the R i Each of them is independently selected from any one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted 9,10-benzophenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted carbazole, or substituted or unsubstituted aromatic amino groups; The substituents are selected from any one of C1-C10 alkyl, C3-C10 cycloalkyl, C1-C6 alkoxy, C6-C60 aryl, and C6-C60 heteroaryl.

[0024] In one implementation, the R i Each of them is independently selected from any one of the following groups: R1-R7 are each independently selected from any one of hydrogen, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C6 alkoxy, C6-C60 aryl, and C6-C60 heteroaryl. An asterisk indicates a connection point.

[0025] In this invention, R i The preferred structure can, on the one hand, enhance the transport of holes or electrons, enabling them to recombine rapidly in the light-emitting layer; on the other hand, it can increase steric hindrance, thus reducing exciton quenching as the main light-emitting material.

[0026] In one embodiment, each of R1-R7 is independently selected from hydrogen, C1-C10 alkyl, C3-C10 cycloalkyl, and C6-C60 aryl.

[0027] In one embodiment, R1 and R2 are each independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, and cyclohexyl; R3 is selected from any one of hydrogen, methyl, ethyl, propyl, and phenyl. R4-R7 are each independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, cyclohexyl, and phenyl.

[0028] In one implementation, the R i Each of them is independently selected from any one of the following groups: An asterisk indicates a connection point.

[0029] In this invention, R i Further optimization of the above structure can, on the one hand, enhance the transmission of holes or electrons, enabling holes and electrons to recombine rapidly in the light-emitting layer; on the other hand, it can increase the steric hindrance, thus reducing exciton quenching as the main light-emitting material.

[0030] In one implementation, j is an integer from 1 to 3.

[0031] In one implementation, the R c Selected from H or .

[0032] In this invention, R c Pyridyl groups are preferred, as they can increase the electron transport capability of organic compounds.

[0033] In one implementation, X is selected from CR. c R c When H is selected, p is not 0.

[0034] In one embodiment, the organic compound is selected from any one of the following compounds: .

[0035] In a second aspect, the present invention provides an OLED display panel, the OLED display panel comprising a first electrode, a second electrode, and an organic thin film layer disposed between the first electrode and the second electrode; the organic thin film layer comprising a light-emitting layer; the main material of the light-emitting layer comprising any one or a combination of at least two of the organic compounds described in the first aspect.

[0036] In one embodiment, the organic thin film layer further includes any one or a combination of at least two of the following: hole injection layer (HIL), hole transport layer (HTL), electron blocking layer (EBL), hole blocking layer (HBL), electron transport layer (ETL), and electron injection layer (EIL).

[0037] In the OLED display panel provided by this invention, the first electrode (anode) material can be selected from metals, such as copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, and their alloys. The first electrode material can also be selected from metal oxides, such as indium oxide, zinc oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc. The first electrode material can also be selected from conductive polymers, such as polyaniline, polypyrrole, poly(3-methylthiophene), etc. Furthermore, the first electrode material can also be selected from materials and combinations thereof that facilitate hole injection, in addition to the first electrode materials listed above, including known materials suitable for use as the first electrode.

[0038] In the OLED display panel provided by this invention, the second electrode (cathode) material can be selected from metals, such as aluminum, magnesium, silver, indium, tin, titanium, and their alloys. The second electrode material can also be selected from multilayer metal materials, such as LiF / Al, LiO2 / Al, BaF2 / Al, etc. Besides the second electrode materials listed above, the second electrode material can also be materials and combinations thereof that facilitate electron injection, including known materials suitable for use as a second electrode.

[0039] The substrate of an OLED display panel can be a rigid substrate, such as borosilicate glass, float soda-lime glass, high refractive index glass, stainless steel, etc., or a flexible substrate, such as polyimide (PI) plastic substrate, polyethylene terephthalate (PET) plastic substrate, polyethylene naphthalate (PEN) plastic substrate, polyethersulfone resin substrate (PES), polycarbonate plastic substrate (PC), ultrathin flexible glass substrate, metal foil substrate, etc.

[0040] In the OLED display panel provided by this invention, the hole injection material, hole transport material, and electron blocking material can each be independently selected from 2,2'-dimethyl-N,N'-di-1-naphthyl-N,N'-diphenyl[1,1'-biphenyl]-4,4'-diamine (α-NPD), 4,4',4”-tris(carbazole-9-yl)triphenylamine (TCTA), 1,3-dicarbazole-9-ylbenzene (mCP), 4,4'-di(9-carbazole)biphenyl (CBP), 3,3'-di(N-carbazole)-1,1'-biphenyl (mCBP), 2,3,6,7,10,11-hexacyano-1,4,5,8,9 Materials include, but are not limited to, 12-hexaazabenzophenanthrene (HATCN), 4,4'-cyclohexylbis[N,N-di(4-methylphenyl)aniline (TAPC), N,N'-diphenyl-N,N'-(1-naphthyl)-1,1'-biphenyl-4,4'-diamine (α-NPB), N,N'-di(naphthyl-2-yl)-N,N'-di(phenyl)biphenyl-4,4'-diamine (NPB), poly(3,4-ethylenedioxythiophene)-polystyrene sulfonic acid (PEDOT:PSS), polyvinylcarbazole (PVK), 9-phenyl-3,9-bicarbazole (CCP), molybdenum trioxide (MoO3), etc.

[0041] In the OLED display panel provided by this invention, the hole blocking material, electron transport material, and electron injection material can each be independently selected from 2,8-bis(diphenylphosphineoxy)dibenzothiophene (PPT), TSPO1, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene (TPBi), 2,8-bis(diphenylphosphoxy)dibenzofuran (PPF), bis(2-diphenylphosphineoxy)diphenyl ether (DPEPO), lithium fluoride (LiF), 4,6-bis(3,5-di(3-pyridinylphenyl)-2-methylpyrimidine (B3PYMPM), 4,7-diphenyl-1,10-phenanthroline (Bphen), and 1,3,5-tris[(3-pyridinyl)-3-phenyl]benzene (TmPyBP). Materials such as tris[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane (3TPYMB), 1,3-bis(3,5-dipyridin-3-ylphenyl)benzene (B3PYPB), 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene (BMPYPHB), 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine (T2T), diphenylbis[4-(pyridin-3-yl)phenyl]silane (DPPS), cesium carbonate (Cs2O3), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 8-hydroxyquinoline-lithium (Liq), and tris(8-hydroxyquinoline)aluminum (Alq3) are used, but are not limited to the above-mentioned materials.

[0042] In the OLED display panel provided by this invention, the light-emitting layer may include a host material and a guest material. The host material may be selected from 2,8-bis(diphenylphosphino)dibenzothiophene, 4,4'-bis(9-carbazole)biphenyl, 3,3'-bis(N-carbazole)-1,1'-biphenyl, 2,8-bis(diphenylphosphino)dibenzofuran, bis(4-(9H-carbazole-9-yl)phenyl)diphenylsilane, 9-(4-tert-butylphenyl)-3,6-bis(triphenylsilyl)-9H-carbazole, bis(2-diphenylphosphino)diphenyl ether, 1,3-bis[3,5-bis(pyridin-3-yl)phenyl]benzene, and 4,6-bis(3,5-bis(3-pyridin)phenyl)-2-methylpyrimidine. The material may be any one or more of the following: 9-(3-(9H-carbazolyl-9-yl)phenyl)-9H-carbazolyl-3-cyano, 9-phenyl-9-[4-(triphenylsilyl)phenyl]-9H-fluorene, 1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene, diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide, 4,4',4”-tris(carbazolyl)triphenylamine, 2,6-dicarbazolyl-1,5-pyridine, polyvinylcarbazole, and polyfluorene; or any one or a combination of at least two of the organic compounds provided in the first aspect of the present invention; the guest material may be selected from one or more of the following: fluorescent materials, phosphorescent materials, thermally activated delayed fluorescence materials, and aggregation-induced emission materials.

[0043] In this embodiment of the invention, the manufacturing process of the OLED display panel is as follows: an anode (first electrode) is formed on a smooth, transparent or opaque substrate; an organic thin layer is formed on the anode; and a cathode (second electrode) is formed on the organic thin layer. The organic thin layer can be formed using known film-forming methods such as vapor deposition, sputtering, spin coating, immersion, and ion plating.

[0044] Thirdly, the present invention provides an electronic device, the electronic device comprising the OLED display panel described in the second aspect.

[0045] In one embodiment, the electronic device may be a mobile phone, computer, LCD TV, smartwatch, smart car, VR or AR headset, etc.

[0046] This invention provides several exemplary methods for preparing organic compounds with the structure of formula (1). In the following examples, the synthesis of the organic compounds is described exemplary. The exemplary organic compounds synthesized and the raw materials used are shown in Table 1 below: Table 1 Example 1: Synthesis of Compound H06 1) Synthesis of intermediate c-1 Under a nitrogen atmosphere, 500 mL of acetonitrile was added to a reaction flask, followed by intermediate b-1 (2 mmol), reactant a-1 (2.1 mmol), K₂CO₃ (7 mmol), catalyst CuI (0.5 mmol), and ligand 18-crown-6 (0.5 mmol). The mixture was heated to 100 °C and reacted for 24 h. After the reaction was complete, the mixture was cooled to room temperature, and the organic phase was collected by filtration. The organic phase was extracted three times with 500 mL of dichloromethane / H₂O at a volume ratio of 5:5. The collected organic phase was dried over anhydrous Na₂SO₄, and the filtrate was collected by filtration. The solvent was removed by rotary evaporation, and the filtrate was purified by column chromatography to obtain intermediate c-1.

[0047] 2) Synthesis of intermediate e-1 Under a nitrogen atmosphere, raw material c-1 (0.1 mol), raw material d-1 (0.12 mol), tetrakis(triphenylphosphine)palladium 0.005 mol, and potassium carbonate 0.3 mol were mixed with 280 mL of toluene, 60 mL of ethanol, and 60 mL of water and stirred at 110 °C. o Stir for 12 hours. After the reaction is complete, the mixture is extracted with dichloromethane, the extract is dried over anhydrous sodium sulfate, filtered, and the filtrate is purified by vacuum distillation and silica gel column chromatography to obtain intermediate e-1.

[0048] 3) Synthesis of compound H06 e-1 (40 mmol) and f-1 (60 mmol) were dissolved in glacial acetic acid (700 ml) and reacted for 10 hours. After the reaction, the resulting substance was introduced into H2O (500 ml), and the solid was purified and dried with water and methanol. The resulting compound and 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (50 mmol) were dissolved in dichloromethane (300 ml), and reacted for 2 hours. The reaction mixture was extracted with benzene solvent and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. Purification by column chromatography or distillation yielded compound H06.

[0049] Example 2-12 In Examples 2-12, compounds H01, H12, H17, H21, H41, H42, H46, H47, H65, H94, and H102 were provided, respectively. The preparation method was the same as in Example 1. The raw materials and intermediates corresponding to these compounds are listed in Table 1 above. The difference is that compounds H01 and H21 were prepared by only steps 1) and 3), and in step 1), the molar ratio of a-1 to b-2 was 2.1:1 and the molar ratio of a-2 to b-2 was 2.1:1, respectively.

[0050] The compounds prepared in the above examples were identified by matrix-assisted laser desorption / ionization time-of-flight mass spectrometry (MALDI-TOF MS) and elemental analysis, and the results are shown in Table 2 below.

[0051] Table 2 Application Example 1 This application example provides an OLED device, the schematic diagram of which is shown below. Figure 1 As shown, the organic electroluminescent device includes: a substrate 1, an ITO anode 2, a first hole transport layer 3, a second hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a first electron transport layer 7, a second electron transport layer 8, a cathode 9 (a magnesium-silver electrode with a magnesium-silver mass ratio of 9:1), and a capping layer (CPL) 10. The thickness of the ITO anode 2 is 15 nm, the thickness of the first hole transport layer 3 is 10 nm, the thickness of the second hole transport layer 4 is 95 nm, the thickness of the electron blocking layer 5 is 30 nm, the thickness of the light-emitting layer 6 is 30 nm, the thickness of the first electron transport layer 7 is 30 nm, the thickness of the second electron transport layer 8 is 5 nm, the thickness of the magnesium-silver electrode 9 is 15 nm, and the thickness of the capping layer (CPL) 10 is 100 nm. Figure 1 The middle arrow indicates the light emission direction of the organic electroluminescent device.

[0052] The fabrication steps of this OLED device are as follows: (1) Cut the glass substrate 1 into 50 mm × 50 mm × 0.7 mm pieces, sonicate them in isopropanol and deionized water for 30 min respectively, and then clean them by exposing them to ozone for about 10 min; mount the resulting glass substrate with ITO anode 2 onto a vacuum deposition equipment. (2) Hole buffer layer material HAT-CN with a thickness of 2 nm and HT-1 with a thickness of 8 nm are deposited on ITO anode 2 by vacuum evaporation. This layer serves as the first hole transport layer 3. (3) Vacuum evaporation of material HT-1 for the second hole transport layer 4 on the first hole transport layer 3 to obtain a layer with a thickness of 95nm, which serves as the second hole transport layer 4. (4) Prime-1 material is deposited on the second hole transport layer 4 to obtain a layer with a thickness of 30 nm, which serves as the electron blocking layer 5; (5) A light-emitting layer 6 is co-deposited on the electron blocking layer 5, wherein the organic compound H01 provided by the present invention is used as the host material and Ir(piq)2(acac) is used as the dopant material, the mass ratio of organic compound H01 to Ir(piq)2(acac) is 19:1, and the thickness is 30 nm. (6) The first electron transport layer 7 compound ET-1 was vacuum evaporated on the light-emitting layer 6 to obtain the first electron transport layer 7 with a thickness of 30 nm; (7) The material LiF for the second electron transport layer 8 is vacuum evaporated on the first electron transport layer 7 to obtain the second electron transport layer 8 with a thickness of 5 nm; (8) Magnesium silver was vacuum deposited on the second electron transport layer 8 to obtain a cathode 9 with a thickness of 15 nm, wherein the mass ratio of Mg:Ag is 9:1; (9) A high-refractive-index hole-type material CPL-1 with a thickness of 100 nm is vacuum-deposited on the cathode 9 and used as a cathode capping layer (capping layer or CPL) 10.

[0053] The structural formulas of the materials HAT-CN, HT-1, Prime-1, Ir(piq)2(acac), ET-1, and CPL-1 mentioned in the above steps are shown below: Application Example 2 The only difference between this application example and application example 1 is that the organic compound H01 in step (5) is replaced with an equal mass of the organic compound H06 provided by the present invention; all other preparation steps are the same.

[0054] Application Example 3 The only difference between this application example and application example 1 is that the organic compound H01 in step (5) is replaced with an equal mass of the organic compound H12 provided by the present invention; all other preparation steps are the same.

[0055] Application Example 4 The only difference between this application example and application example 1 is that the organic compound H01 in step (5) is replaced with an equal mass of the organic compound H17 provided by the present invention; all other preparation steps are the same.

[0056] Application Example 5 The only difference between this application example and application example 1 is that the organic compound H01 in step (5) is replaced with an equal mass of the organic compound H21 provided by the present invention; all other preparation steps are the same.

[0057] Application Example 6 The only difference between this application example and application example 1 is that the organic compound H01 in step (5) is replaced with an equal mass of the organic compound H41 provided by the present invention; all other preparation steps are the same.

[0058] Application Example 7 The only difference between this application example and application example 1 is that the organic compound H01 in step (5) is replaced with an equal mass of the organic compound H42 provided by the present invention; all other preparation steps are the same.

[0059] Application Example 8 The only difference between this application example and application example 1 is that the organic compound H01 in step (5) is replaced with an equal mass of the organic compound H46 provided by the present invention; all other preparation steps are the same.

[0060] Application Example 9 The only difference between this application example and application example 1 is that the organic compound H01 in step (5) is replaced with an equal mass of the organic compound H47 provided by the present invention; all other preparation steps are the same.

[0061] Application Example 10 The only difference between this application example and application example 1 is that the organic compound H01 in step (5) is replaced with an equal mass of the organic compound H65 provided by the present invention; all other preparation steps are the same.

[0062] Application Example 11 The only difference between this application example and application example 1 is that the organic compound H01 in step (5) is replaced with an equal mass of the organic compound H94 provided by the present invention; all other preparation steps are the same.

[0063] Application Example 12 The only difference between this application example and application example 1 is that the organic compound H01 in step (5) is replaced with an equal mass of the organic compound H102 provided by the present invention; all other preparation steps are the same.

[0064] Comparative Application Example 1 The only difference between this comparative application example and application example 1 is that the organic compound H01 in step (5) is replaced with an equal mass of the comparative compound M1. Replace ); all other preparation steps are the same.

[0065] Performance evaluation of OLED devices: The current of the OLED device at different voltages was measured using a Keithley 2365A digital nanovoltmeter, and then the current density of the OLED device at different voltages was obtained by dividing the current by the emitting area. The luminance and radiant energy flux density of the OLED device at different voltages were measured using a Konicaminolta CS-2000 spectroradiometer. Based on the current density and luminance of the OLED device at different voltages, the turn-on voltage and current efficiency (CE, Cd / A) at the same current density (10 mA / cm²) were obtained. on Brightness 1 Cd / m 2 The on-state voltage; the lifetime LT95 (at 50 mA / cm²) is obtained by measuring the time it takes for the OLED device to reach 95% of its initial brightness. 2 (under test conditions) The specific data is shown in Table 3: Table 3 As can be seen from the data in Table 3, compared with the device in Comparative Application Example 1, the electroluminescent device using the organic compound of the present invention has a lower turn-on voltage, which is reduced by about 1% to 2.3% (as shown in Table 3 above, the turn-on voltage is the relative turn-on voltage obtained by taking the turn-on voltage of the device in Comparative Application Example 1 as 100%), thus effectively reducing the power consumption of the device; the device using the organic compound of the present invention has a higher current efficiency, which is improved by about 4.7% to 8.2% compared with Comparative Application Example 1 (as shown in Table 3 above, the current efficiency is the relative current efficiency obtained by taking the current efficiency of the device in Comparative Application Example 1 as 100%); the device using the organic compound of the present invention has a longer lifespan, which is extended by about 5.9% to 8.5% compared with the device in Comparative Application Example 1 (as shown in Table 3 above, LT95 is the relative LT95 obtained by taking the LT95 of the device in Comparative Application Example 1 as 100%).

[0066] The applicant declares that the above embodiments illustrate the organic compounds and their applications, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials used in the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in formula (I): Formula (I) In formula (I), L m Selected from any one of single bonds, phenylene, biphenylene, naphthylene, anthraceneylene, and phenanthrene; In equation (I), n is 1 and m is 1; In equation (I), R i It is selected from any one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthraquinyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted 9,10-benzophenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted carbazole, and substituted or unsubstituted aromatic amino groups; The aromatic amino group is a diphenylamino group; In equation (I), j is 1 and i is 1; In formula (I), X is selected from N; In equation (I), p is 0; In equation (I), the dashed line represents a single bond; The substituents are selected from any one of C1-C10 alkyl, C3-C10 cycloalkyl, C1-C6 alkoxy, and C6-C10 aryl.

2. The organic compound according to claim 1, characterized in that, The L m It is selected from any one of single bonds, phenylene, and biphenylene.

3. The organic compound according to claim 1, characterized in that, The L m Selected from single bonds or any of the following groups: In this context, the asterisk (*) indicates a connection point.

4. The organic compound according to claim 1, characterized in that, The L m Selected from single bonds or any of the following groups: In this context, the asterisk (*) indicates a connection point.

5. The organic compound according to claim 1, characterized in that, The R i It is selected from any one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted 9,10-benzophenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted carbazole, and substituted or unsubstituted aromatic amino groups; The aromatic amino group is a diphenylamino group; The substituents are selected from any one of C1-C10 alkyl, C3-C10 cycloalkyl, C1-C6 alkoxy, and C6-C10 aryl.

6. The organic compound according to claim 1, characterized in that, The R i Selected from any one of the following groups: R1-R7 are each independently selected from any one of hydrogen, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C6 alkoxy, and C6-C10 aryl; An asterisk indicates a connection point.

7. The organic compound according to claim 6, characterized in that, Each of R1-R7 is independently selected from hydrogen, C1-C10 alkyl, C3-C10 cycloalkyl, and C6-C10 aryl.

8. The organic compound according to claim 6, characterized in that, R1 and R2 are each independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, and cyclohexyl; R3 is selected from any one of hydrogen, methyl, ethyl, propyl, and phenyl. R4-R7 are each independently selected from any one of hydrogen, methyl, ethyl, propyl, n-butyl, isobutyl, tert-butyl, cyclohexyl, and phenyl.

9. The organic compound according to claim 1, characterized in that, The R i Selected from any one of the following groups: An asterisk indicates a connection point.

10. The organic compound according to claim 1, characterized in that, The organic compound is selected from any one of the following compounds: 。 11. An OLED display panel, characterized in that, The OLED display panel includes a first electrode, a second electrode, and an organic thin film layer disposed between the first electrode and the second electrode; The organic thin film layer includes a light-emitting layer; The main material of the light-emitting layer includes any one or a combination of at least two of the organic compounds described in any one of claims 1-10.

12. The OLED display panel according to claim 11, characterized in that, The organic thin film layer further includes any one or a combination of at least two of the following: a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

13. An electronic device, characterized in that, The electronic device includes the OLED display panel as described in claim 11 or 12.

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