Organic Compounds, OLED Devices, Display Panels and Display Devices

Abstract

The present application discloses an organic compound, an OLED device, a display panel, and a display device. The organic compound in the present application has a structure shown in the following formula I, wherein R 1 and R 2 are independently selected from hydrogen, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group. The organic compound of the present application is a fused macrocycle obtained by fusing six rings in the core part. The nitrogen atom in the core part of the pyrrolopyrrole skeleton on the macrocycle improves the hole transport ability of the entire compound, can improve the recombination probability of electrons and holes in the light-emitting layer of an organic electroluminescent device, enhance the light-emitting efficiency, and the macrocycle has excellent thermal and charge tolerance, and is expected to achieve a long lifespan. #imgabs0#

Description

Technical Field

[0001] This application relates to the field of organic light-emitting technologies, and particularly to an organic compound, an OLED device, a display panel, and a display device. Background Art

[0002] As a new generation of display technology, organic light-emitting devices (OLEDs) have the advantages of self-luminescence, wide viewing angles, high contrast ratios, low power consumption, and fast response speeds, and are now widely used in the display field.

[0003] An OLED includes a cathode, an anode, and an organic thin film layer. Among them, the organic thin film layer contains a light-emitting material. The cathode and the anode inject electrons and holes into the organic thin film layer respectively. These electrons and holes combine within the light-emitting material to generate electron-hole pairs, that is, excitons. When these excitons return from the excited state to the stable ground state, they can release energy in the form of light, thereby emitting visible light. Therefore, in an OLED, by selecting different light-emitting materials, visible light of different colors can be generated to meet the requirements of full-color display.

[0004] Currently, the phosphorescent materials currently in use have problems such as insufficiently long lifetimes, low efficiency, and relatively high driving voltages. Summary of the Invention

[0005] This application provides an organic compound, a display panel, and a display device. This organic compound can improve the luminous efficiency and service life of an organic light-emitting device.

[0006] In a first aspect, an embodiment of this application provides an organic compound having a structural formula shown in Formula I:

[0007]

[0008] Wherein, R 1 and R 2 are independently selected from hydrogen, a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group.

[0009] In a second aspect, an embodiment of this application provides an OLED device. The OLED device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode. The material of the organic thin film layer includes the above-mentioned organic compound.

[0010] In a third aspect, an embodiment of this application provides a display panel. The display panel includes the above-mentioned OLED device.

[0011] In a fourth aspect, an embodiment of this application provides a display device including the above-mentioned display panel.

[0012] Compared with the prior art, the present application has at least the following beneficial effects:

[0013] In the technical solution of the present application, the skeleton of the organic compound has an electron-donating ability, and a group with an electron-withdrawing ability is connected to the skeleton, so that the compound has a bipolar structure. This structure is conducive to the transmission and recombination of electrons and holes, thereby improving the light-emitting efficiency of the device having it. The introduction of adamantane effectively expands the intermolecular distance, reduces the intermolecular interaction, reduces exciton quenching, improves the energy utilization rate, and further improves the device efficiency. At the same time, this structure can reduce the molecular force, reduce the intermolecular stacking, is conducive to reducing concentration quenching and efficiency roll-off, and enables the device to have a long service life. In addition, the organic compound can also reduce the turn-on voltage of the device. BRIEF DESCRIPTION OF THE DRAWINGS

[0014] In order to more clearly illustrate the technical solutions of the embodiments of the present application, the following will briefly introduce the drawings required to be used in the embodiments of the present application. Obviously, the following described drawings are only some embodiments of the present application. For those of ordinary skill in the art, other drawings can be obtained according to the drawings without creative efforts.

[0015] Figure 1 It is a schematic structural diagram of an OLED device provided by some embodiments of the present application.

[0016] Description of the reference numerals:

[0017] Substrate 1, ITO anode 2, first hole transport layer 3, second hole transport layer 4, electron blocking layer 5, light-emitting layer 6, first electron transport layer 7, second electron transport layer 8, cathode 9, cover layer 10. DETAILED DESCRIPTION OF THE EMBODIMENTS

[0018] In order to make the invention purpose, technical solution and beneficial technical effects of the present application clearer, the following further details the present application in conjunction with embodiments. It should be understood that the embodiments described in this specification are only for explaining the present application and not for limiting the present application.

[0019] The above-mentioned inventive content of the present application does not intend to describe each disclosed embodiment or each implementation manner in the present application. The following description more specifically exemplifies exemplary embodiments. Throughout the application, guidance is provided through a series of embodiments, which can be used in various combinations. In each instance, the enumeration is only as a representative group and should not be construed as exhaustive.

[0020] In the description herein, unless otherwise specified, "above" and "below" include the present number, and the meanings of "one or more" and "one or more" in "multiple" and "multiple" are two or more.

[0021] The terms "a" and "the" each refer to one or more molecules of the compound and are not limited to a single molecule of the compound. In addition, the one or more molecules may be the same or may be different, so long as they fall within the scope of the chemical compound.

[0022] The term "comprising" and variations thereof as used in the specification and claims is not limiting.

[0023] The terms "preferred" and "preferably" refer to embodiments of the present application that in certain circumstances may provide certain benefits. However, in the same or other circumstances, other embodiments may also be preferred. In addition, the recitation of one or more preferred embodiments does not mean that other embodiments are not available and is not intended to exclude other embodiments from the scope of the present disclosure.

[0024] The grouping of alternative elements or embodiments disclosed herein should not be construed as limiting. Each member of the group may be employed and claimed separately, or in any combination with other members of the group or other elements found herein. It is contemplated that, for reasons of convenience and / or patentability, one or more members of the group may be included in or deleted from the group. When any such inclusion or deletion occurs, the specification is hereby regarded as containing the modified group and thus meets the written description of all Markush groups used in the claims.

[0025] Unless otherwise indicated, when a compound or chemical structure feature (e.g., aryl) is referred to as "substituted", the feature may have one or more substituents. The term "substituent" has the broadest meaning known to those of ordinary skill in the art and includes such moieties that occupy positions normally occupied by one or more hydrogen atoms attached to the parent compound or chemical structure feature.

[0026] The term "aryl" refers to a closed aromatic ring or ring system. Examples of aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, biphenyl (including biphenylyl, terphenyl), triphenylene, pyrenyl, spirobifluorenyl, -yl, perylenyl, indenyl, azulyl, and benzo[ghi]phenanthrenyl. In various embodiments, C6-C30 aryl, i.e., aryl, may contain 6-30 carbon atoms for forming the ring.

[0027] The term "heteroaryl" means that one or more atoms in the ring of an aryl group are elements other than carbon. In some embodiments, as a whole, a C5-C30 heteroaryl group may contain 5-25, 5-18, or 6-12 ring heteroatoms (such as N, O, etc.). Examples of heteroaryl groups include, but are not limited to, pyrrolyl, furyl, oxazolyl, isoxazolyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, oxadiazolyl, imidazolyl, pyrazolyl, triazole, pyridazinyl, pyrazinyl, pyridyl, pyrimidinyl, triazinyl, indolyl, quinolinyl, isoquinolinyl, acridinyl, purinyl, pteridinyl, benzofuryl, benzothienyl, benzimidazolyl, benzothiazolyl, benzotriazolyl, benzoxadiazolyl, benzoxazolyl, cinnoline, quinoxalinyl, dibenzofuryl, dibenzothienyl, carbazolyl, phenanthrolinyl, indazyl, naphthyridinyl, and phthalazinyl. In various embodiments, a C5-C30 heteroaryl group, i.e., a heteroaryl group, may contain 5-30 carbon atoms for forming a ring.

[0028] In this document, the representation of a single bond passing through a ring or a ring system means that the single bond can be connected to any accessible position of the ring or the ring system.

[0029] Organic compound

[0030] In a first aspect, an embodiment of the present application provides an organic compound having a structural formula shown in Formula I:

[0031]

[0032] Wherein, R 1 and R 2 are independently selected from hydrogen, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C3-C30 heteroaryl group.

[0033] In the embodiments of the present application, each of C6-C30 can independently be C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.

[0034] In the embodiments of the present application, each of C3-C30 can independently be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.

[0035] The organic compound provided by the embodiment of the present application is a fused cyclic compound including a fused macrocycle obtained by fusing six rings in the core part. The nitrogen atom in the core part of the pyrrolopyrrole skeleton on the macrocycle improves the hole transport ability of the whole compound, can improve the recombination probability of electrons and holes in the light-emitting layer of the organic light-emitting device, enhance the light-emitting efficiency, and the macrocycle has excellent thermal and charge tolerance, and is expected to achieve a long lifespan; an electron-withdrawing group is connected to one side or both sides of the fused macrocycle, which can improve the electron transport ability of the whole compound, make the whole molecule bipolar, and a adamantane structure with large steric hindrance is connected to one side, which will effectively reduce the close packing of the molecules, thereby reducing the quenching of excitons, improving the utilization rate of excitons, and effectively realizing the dispersion of excitons, so that the lifespan and stability of the device can be improved.

[0036] In some embodiments, the organic compound is selected from any one of the compounds represented by the following formula II or formula III:

[0037]

[0038] Wherein, R 1 and R 2 are independently selected from hydrogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl.

[0039] In the embodiment of the present application, C6-C30 can be independently C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.

[0040] In the embodiment of the present application, C3-C30 can be independently C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.

[0041] In some embodiments, the organic compound is selected from any one of the compounds represented by the following formula IV to formula VII:

[0042]

[0043] Wherein, R 1 is selected from hydrogen, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl; R 3Selected from hydrogen, substituted or unsubstituted C6-C24 aryl, and substituted or unsubstituted C3-C24 heteroaryl.

[0044] In the embodiments of the present application, each of C6-C30 can independently be C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.

[0045] In the embodiments of the present application, each of C3-C30 can independently be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29, C30, etc.

[0046] In the embodiments of the present application, each of C6-C24 can independently be C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, etc.

[0047] In the embodiments of the present application, each of C3-C24 can independently be C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, etc.

[0048] In some embodiments, the substituted or unsubstituted C6-C24 aryl includes phenyl and its cyano-substituted derivatives, biphenyl and its cyano-substituted derivatives, terphenyl and its cyano-substituted derivatives, naphthyl and its cyano-substituted derivatives, anthracenyl and its cyano-substituted derivatives, phenanthrenyl and its cyano-substituted derivatives, pyrenyl and its cyano-substituted derivatives, fluorenyl and its cyano-substituted derivatives, and fluorenyl and its cyano-substituted derivatives.

[0049] In the organic compounds of the embodiments of the present application, an electron-withdrawing group is connected to one or both sides of the fused macrocycle, which can improve the electron transport ability of the whole compound, making the whole molecule bipolar. Connecting an adamantane structure with large steric hindrance to one side will effectively reduce the close packing of the molecules, thereby reducing the quenching of excitons, improving the utilization rate of excitons, effectively realizing the dispersion of excitons, and thus improving the lifetime and stability of the device.

[0050] In some embodiments, the substituted or unsubstituted C6-C24 heteroaryl includes pyridyl, quinolinyl, isoquinolinyl, benzo[b]pyridyl substituted with C6-C12 (such as C6, C7, C8, C9, C10, C11, C12, etc.) aryl, pyrazinyl, benzo[b]pyrazinyl, benzo[b]pyrazinyl substituted with C6-C12 (such as C6, C7, C8, C9, C10, C11, C12, etc.) aryl, pyridazinyl, benzo[b]pyridazinyl, benzo[b]pyridazinyl substituted with C6-C12 (such as C6, C7, C8, C9, C10, C11, C12, etc.) aryl, imidazolyl, benzimidazolyl, benzimidazolyl substituted with C6-C12 (such as C6, C7, C8, C9, C10, C11, C12, etc.) aryl, pyrimidinyl, pyrimidinyl substituted with C6-C12 (such as C6, C7, C8, C9, C10, C11, C12, etc.) aryl, benzo[b]pyrimidinyl substituted with C6-C12 (such as C6, C7, C8, C9, C10, C11, C12, etc.) aryl, benzoxazolyl, benzothiazolyl, benzothiazolyl substituted with C6-C12 (such as C6, C7, C8, C9, C10, C11, C12, etc.) aryl, phenanthrolinyl, dibenzofuranyl, dibenzothiophenyl, diphenyltriazinyl and tripyridyl.

[0051] In some embodiments, the substituted or unsubstituted C6-C30 aryl includes phenyl and its cyano-substituted derivatives, biphenyl and its cyano-substituted derivatives, terphenyl and its cyano-substituted derivatives, naphthyl and its cyano-substituted derivatives, anthryl and its cyano-substituted derivatives, phenanthryl and its cyano-substituted derivatives, pyrenyl and its cyano-substituted derivatives, anthracenyl and its cyano-substituted derivatives and fluorenyl and its cyano-substituted derivatives.

[0052] In some embodiments, the substituted or unsubstituted C6-C30 aryl includes at least one of the substituents represented by Formula A-1 to Formula A-20:

[0053]

[0054] Wherein, # represents the connection site.

[0055] In some embodiments, the substituted or unsubstituted C3-C30 heteroaryl includes at least one of the substituents represented by Formula E-1 to Formula E-20:

[0056]

[0057]

[0058] Wherein, # represents the connection site.

[0059] In some embodiments, R 1 and R 2are the same substituents.

[0060] According to an embodiment of the present application, when R 1 and R 2 are the same substituents, the structure of the organic compound has symmetry. The organic compound containing a symmetric structure has strong stability. When used as a material for the multi-layer organic film layer in an OLED, it can extend the service life of the light-emitting device, and the organic compound with a symmetric structure has low requirements for synthesis conditions and a simple synthesis method.

[0061] In some embodiments, the organic compound is selected from any one of the compounds represented by Formula D-1 to Formula D-33 as follows:

[0062]

[0063]

[0064]

[0065] In some embodiments, the organic compound is selected from any one of the compounds represented by Formula K-1 to Formula K-36 as follows:

[0066]

[0067]

[0068]

[0069] In some embodiments, R 1 and R 2 are different substituents.

[0070] In some embodiments, one of R 1 and R 2 is hydrogen, and the other is one of Formula A1-A33 or one of Formula E1-E54. For the structural formulas of Formula A1-A33 and Formula E1-E54, please refer to the foregoing, and details are not described herein again.

[0071] In some embodiments, the organic compound is selected from any one of the compounds represented by Formula P-1 to Formula P-83 as follows:

[0072]

[0073]

[0074]

[0075]

[0076]

[0077]

[0078] OLED device

[0079] In a second aspect, an embodiment of the present application provides an OLED device. The OLED device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode. The material of the organic thin film layer includes the above-mentioned organic compound. The material of the organic thin film layer can be one of the above-mentioned organic compounds, or can include a mixture of two or more of the above-mentioned organic compounds.

[0080] In some embodiments, the anode material may include metals (such as copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, etc. and their alloys), metal oxides (such as indium oxide, zinc oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc.), conductive polymers (such as polyaniline, polypyrrole, poly(3-methylthiophene), etc.). In addition to the above materials and their combinations that are helpful for hole injection, other known materials suitable for making an anode can also be included.

[0081] In some embodiments, the cathode may include a metal layer (such as aluminum, magnesium, silver, indium, tin, titanium, etc. and their alloys), a multi-layer cathode formed by laminating a metal layer and a layer containing one or several of metal oxides and metal halides (such as LiF / Al, LiO2 / Al, BaF2 / Al, etc.). In addition to the above materials and their combinations that are helpful for electron injection, other known materials suitable for making a cathode are also included.

[0082] In some embodiments of the present application, the organic thin film layer further includes an electron transport region and / or a hole transport region, wherein the electron transport region and the hole transport region include one or more of the organic compounds in any of the above embodiments.

[0083] In an embodiment of the present application, the electron transport region refers to the region where electrons move between the cathode and the light-emitting layer. Exemplarily, the electron transport region may include at least one layer of an electron injection layer, an electron transport layer, and a hole blocking layer, and one or more of the organic compounds in any of the above embodiments are included in at least one layer.

[0084] Exemplarily, the electron transport region includes a first electron transport layer and a second electron transport layer stacked, and the materials of the first electron transport layer and the second electron transport layer include one or more of the organic compounds in any of the above embodiments.

[0085] The hole transport region refers to the region where holes move between the anode and the light-emitting layer. Exemplarily, the hole transport region may include at least one layer of a hole injection layer, a hole transport layer, and an electron blocking layer, and one or more of the organic compounds in any of the above embodiments are included in at least one layer.

[0086] Exemplarily, the hole transport region includes a first hole transport layer, a second hole transport layer, and an electron blocking layer stacked on top of each other, and the materials of the first hole transport layer, the second hole transport layer, and the electron blocking layer include one or more of the organic compounds in any of the above embodiments.

[0087] OLED devices can be fabricated using methods known in the art. Exemplary fabrication methods include: forming an anode on a transparent or opaque smooth substrate, forming a multi-layer organic thin film layer on the anode, and forming a cathode on the organic thin film layer. Known film-forming methods such as evaporation, sputtering, spin coating, dipping, ion plating, etc. can be used to form the organic thin film layer.

[0088] Figure 1 An OLED device shown as an example 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, and a cover layer 10 stacked in sequence.

[0089] Display panel

[0090] In a third aspect, an embodiment of the present application provides a display panel, and the display panel includes the above-mentioned OLED device.

[0091] The display panel and the display device of the present application contain the organic compound of the first aspect of the present application, and thus can have good luminous efficiency, low driving voltage, and long service life. Since expensive noble metals and other substances are not used, they also have advantages such as low cost.

[0092] Display device

[0093] In a fourth aspect, an embodiment of the present application provides a display device, including the above-mentioned display panel. Examples of the display device include but are not limited to mobile phones, computers, televisions, smart watches, smart cars, VR or AR helmets, etc., and the present application does not make special limitations on this.

[0094] According to the embodiments of the present application, since the display panel and the display device contain the organic compound provided by the present application, they can have good luminous efficiency, low driving voltage, and long service life. Since expensive noble metals and other substances are not used, they also have advantages such as low cost.

[0095] Synthesis of Organic Compounds

[0096] The present application exemplarily provides several methods for preparing organic compounds. Other compounds of the present application can be prepared with reference to this exemplary method. According to the exemplary compound preparation method, those skilled in the art can easily obtain the specific methods for implementing each synthesis step from relevant scientific literature or standard textbooks in the art. Unless otherwise specified, commercially available or compounds known in the literature are used as raw materials for synthesis. Those skilled in the art of organic synthesis will recognize that, for the purpose of optimizing the generation of the compounds described herein, the nature and order of the proposed synthesis steps can be changed.

[0097] The processes described in the present application can be monitored according to any suitable method known in the art. For example, product formation can be monitored by spectroscopic means such as nuclear magnetic resonance spectroscopy (NMR, e.g., 1H or 13C), infrared spectroscopy (IR), spectrophotometry (e.g., UV-visible), mass spectrometry (MS) or by chromatography such as high performance liquid chromatography (HPLC), gas chromatography (GC), gel permeation chromatography (GPC) or thin layer chromatography (TLC).

[0098] When R 1 and R 2 are the same, the organic compounds provided by the present application can be prepared through the following synthetic route:

[0099]

[0100] Example 1: Synthesis of K-2

[0101] This example provides a method for synthesizing an organic compound, comprising the following steps:

[0102]

[0103] (1) Synthesis of K-2-1: Under an argon (Ar) atmosphere, 170 mmol of reactant A2, 57 mmol of Pd(OAc)2, 1.13 mmol of K2CO3, 205 mmol of reactant B2 and 341 mL of 1,4-dioxane were sequentially added to a 500 mL three-necked flask, and then heated, stirred and refluxed for about 24 hours. After cooling to room temperature, the reaction product was filtered through diatomaceous earth to separate the insoluble residue, water was added, and the organic layer was taken separately. Toluene was added to the aqueous layer, and the organic layer was extracted again. The organic layer thus collected was washed with a saline solution and dried over MgSO4. The MgSO4 was separated, the organic layer was concentrated, and the crude product thus obtained was separated by silica gel column chromatography (using a mixture solvent of hexane and toluene as the eluent) to obtain the intermediate K-2-1.

[0104] (2) Synthesis of K-2-2: Under an argon atmosphere, 63 mmol of K-2-1, 126 mL of o-dichlorobenzene, and 252 mmol of P(OEt)3 were sequentially added to a 300 mL three-necked flask, and then heated and stirred at about 160 °C for about 24 hours. After cooling to room temperature, the reaction solvent was distilled off, and the crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of hexane and toluene as the eluent) to obtain intermediate K-2-2.

[0105] (3) Synthesis of K-2-3: Under an argon atmosphere, 48.5 mmol of intermediate K-2-2, 1.5 mmol of Pd(dba)2, 121 mmol of NaOtBu, 242 mL of toluene, 97 mmol of reactant C2, and 4.8 mmol of PtBu3 were sequentially added to a 500 mL three-necked flask, heated, stirred, and refluxed for about 6 hours. After cooling to room temperature, water was added to the reaction product, and the organic layer was taken separately. Toluene was added to the aqueous layer, and the organic layer was extracted again. The organic layer thus collected was washed with an aqueous saline solution and dried over MgSO4. The MgSO4 was separated, and the organic layer was concentrated, and then the crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of hexane and toluene as the eluent) to obtain intermediate K-2-3.

[0106] (4) Synthesis of K-2-4: Under an argon atmosphere, 120 mmol of magnesium chips, 30 mmol of reactant D2, 3 g of iodine, and 20 mL of anhydrous tetrahydrofuran (THF) solvent were added to a 250 mL two-necked flask, heated and stirred to initiate the Grignard reaction. After initiation, a 100 mL anhydrous THF solution of 70 mmol of compound D2 was added dropwise to the reaction solution, and the reaction was continued at 60 °C for 1 hour. The reaction solution was slowly transferred to a 500 mL three-necked flask containing 100 mmol of K-2-3 and 100 mL of anhydrous THF, and the reaction was carried out at room temperature for 12 hours. After cooling to room temperature, water was added to quench the reaction. The reaction solution was rotary evaporated to remove most of the solvent, dissolved in dichloromethane, washed three times with water, and the organic solution was collected, mixed with silica gel, and purified by column chromatography to obtain intermediate K-2-4.

[0107] (5) Synthesis of K-2: Under an argon stream, 43.6 mmol of reactant K-2-4 and 96 mmol of reactant E2 were dissolved in 150 mL of tetrahydrofuran (THF) solvent, and then an aqueous solution of 87.3 mmol of K2CO3 was added, and the mixture was heated and stirred. Under reflux, 1.3 mmol of Pd(PPh3)4 was added, and the mixture was heated and stirred for 6 hours. After the reaction was completed, the temperature was lowered to room temperature, the K2CO3 solution was removed and filtered. The filtered solid was washed with ethanol to obtain product K-2.

[0108] MALDI-TOF: m / z: Calculated value: C39 H 32 N4: 556.26, measured value: 556.64.

[0109] Elemental analysis results of the compound: Calculated value: C 39 H 32 N4(%) : C, 84.14; H, 5.79; N, 10.06; Test value: C, 84.12; H, 5.80; N, 10.07.

[0110] Example 2: Synthesis of K-19

[0111] This example provides a method for synthesizing an organic compound, which includes the following steps:

[0112]

[0113] (1) Synthesis of K-19-1: Under an argon (Ar) atmosphere, add 170 mmol of reactant A, 19 , 57 mmol of Pd(OAc)2, 1.13 mmol of K2CO3, 205 mmol of reactant B 19 and 341 mL of 1,4-dioxane to a 500 mL three-necked flask in sequence, then heat, stir and reflux for about 24 hours. After cooling to room temperature, filter the reaction product through diatomaceous earth to separate the insoluble residue, add water, and separately take the organic layer. Add toluene to the aqueous layer and extract the organic layer again. Wash the organic layer thus collected with a saline solution and dry it over MgSO4. Separate MgSO4, concentrate the organic layer, and then separate the crude product thus obtained by silica gel column chromatography (using a mixture solvent of hexane and toluene as the eluent) to obtain intermediate K-19-1.

[0114] (2) Synthesis of K-19-2: Under an argon atmosphere, add 63 mmol of K-19-1, 126 mL of o-dichlorobenzene and 252 mmol of P(OEt)3 to a 300 mL three-necked flask in sequence, then heat and stir at about 160 °C for about 24 hours. After cooling to room temperature, distill off the reaction solvent, and separate the crude product thus obtained by silica gel column chromatography (using a mixture solvent of hexane and toluene as the eluent) to obtain intermediate K-19-2.

[0115] (3) Synthesis of K-19-3: Under an argon atmosphere, add 48.5 mmol of intermediate K-19-2, 1.5 mmol of Pd(dba)2, 121 mmol of NaOtBu, 242 mL of toluene, 48.5 mmol of reactant C 194.8 mmol of PtBu3 were added, and the mixture was heated, stirred, and refluxed for about 6 hours. After cooling to room temperature, water was added to the reaction product, and the organic layer was separated separately. Toluene was added to the aqueous layer, and the organic layer was extracted again. The organic layer thus collected was washed with an aqueous saline solution and dried over MgSO4. The MgSO4 was separated, and the organic layer was concentrated. Then, the crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of hexane and toluene as the eluent) to obtain intermediate K-19-3.

[0116] (4) Synthesis of K-19-4: Under an argon atmosphere, 120 mmol of magnesium chips, 30 mmol of reactant D 19 , 3 g of iodine, and 20 mL of anhydrous tetrahydrofuran (THF) solvent were added to a 250 mL two-necked flask. The mixture was heated and stirred to initiate the Grignard reaction. After initiation, a 100 mL anhydrous THF solution of 70 mmol of compound D4 was added dropwise to the reaction solution, and the reaction was continued at 60 °C for 1 hour. The reaction solution was slowly transferred to a 500 mL three-necked flask containing 100 mmol of K-19-3 and 100 mL of anhydrous THF, and the reaction was carried out at room temperature for 12 hours. After cooling to room temperature, the reaction was quenched with water. Most of the solvent was removed by rotary evaporation of the reaction solution. The residue was dissolved in dichloromethane and washed with water three times. The organic solution was collected, mixed with silica gel, and purified by column chromatography to obtain intermediate K-19-4.

[0117] (5) Synthesis of K-19: Under an argon stream, 43.6 mmol of reactant K-19-4 and 95.8 mmol of reactant E 19 were dissolved in 150 mL of tetrahydrofuran (THF) solvent, and then 87.3 mmol of an aqueous K2CO3 solution was added. The mixture was heated and stirred. Under reflux, 1.3 mmol of Pd(PPh3)4 was added, and the mixture was heated and stirred for 6 hours. After the reaction was completed, the temperature was lowered to room temperature, and the K2CO3 solution was removed by filtration. The filtered solid was washed with ethanol to obtain product K-19.

[0118] MALDI-TOF: m / z: Calculated value: C 50 H 38 N6: 722.32, Measured value: 722.86.

[0119] Elemental analysis results of the compound: Calculated value: C 50 H 38 N6 (%) : C, 83.08; H, 5.30; N, 11.63; Test value: C, 83.05; H, 5.31; N, 11.64.

[0120] Example 3: Synthesis of P-1

[0121] This example provides a method for synthesizing an organic compound, which includes the following steps:

[0122]

[0123] (1) Synthesis of P-1-1: Under an argon (Ar) atmosphere, 170 mmol of reactant A1, 57 mmol of Pd(OAc)2, 1.13 mmol of K2CO3, 205 mmol of reactant B, and 341 mL of 1,4-dioxane were sequentially added to a 500 mL three-necked flask, and then heated, stirred, and refluxed for about 24 hours. After cooling to room temperature, the reaction product was filtered through diatomaceous earth to separate the insoluble residue, water was added, and the organic layer was taken separately. Toluene was added to the aqueous layer, and the organic layer was extracted again. The organic layer thus collected was washed with a saline solution and dried over MgSO4. The MgSO4 was separated, the organic layer was concentrated, and then the crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of hexane and toluene as the eluent) to obtain intermediate P-1-1. 19 And 341 mL of 1,4-dioxane, then heated, stirred and refluxed for about 24 hours. After cooling to room temperature, the reaction product was filtered through diatomaceous earth to separate the insoluble residue, water was added, and the organic layer was taken separately. Toluene was added to the aqueous layer, and the organic layer was extracted again. The organic layer thus collected was washed with a saline solution and dried over MgSO4. The MgSO4 was separated, the organic layer was concentrated, and then the crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of hexane and toluene as the eluent) to obtain intermediate P-1-1.

[0124] (2) Synthesis of P-1-2: Under an argon atmosphere, 63 mmol of P-1-1, 126 mL of o-dichlorobenzene, and 252 mmol of P(OEt)3 were sequentially added to a 300 mL three-necked flask, and then heated and stirred at about 160 °C for about 24 hours. After cooling to room temperature, the reaction solvent was distilled off, and the crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of hexane and toluene as the eluent) to obtain intermediate P-1-2.

[0125] (3) Synthesis of P-1-3: Under an argon atmosphere, 48.5 mmol of intermediate P-1-2, 1.5 mmol of Pd(dba)2, 121 mmol of NaOtBu, 242 mL of toluene, 48.5 mmol of reactant C 19 And 4.8 mmol of PtBu3 were added to a 500 mL three-necked flask in sequence, heated, stirred, and refluxed for about 6 hours. After cooling to room temperature, water was added to the reaction product, and the organic layer was taken separately. Toluene was added to the aqueous layer, and the organic layer was extracted again. The organic layer thus collected was washed with a saline solution and dried over MgSO4. The MgSO4 was separated, and the organic layer was concentrated, and then the crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of hexane and toluene as the eluent) to obtain intermediate P-1-3.

[0126] (4) Synthesis of P-1-4: Under an argon atmosphere, 120 mmol of magnesium chips, 30 mmol of reactant D 19, 3 g of iodine and 20 mL of anhydrous tetrahydrofuran (THF) solvent were added to a 250 mL two-necked flask, and the mixture was heated and stirred to initiate the Grignard reaction. After initiation, a 100 mL anhydrous THF solution of 70 mmol of compound D4 was added dropwise to the reaction solution, and the reaction was continued at 60 °C for 1 hour. The reaction solution was slowly transferred to a 500 mL three-necked flask containing 100 mmol of P-1-3 and 100 mL of anhydrous THF, and the reaction was carried out at room temperature for 12 hours. After cooling to room temperature, the reaction was quenched with water. Most of the solvent was removed by rotary evaporation of the reaction solution, and the residue was dissolved in dichloromethane and washed three times with water. The organic layer was collected and purified by silica gel column chromatography to obtain intermediate P-1-4.

[0127] (5) Synthesis of P-1: Under an argon stream, 43.6 mmol of reactant P-1-4 and 47.9 mmol of reactant E1 were dissolved in 150 mL of tetrahydrofuran (THF) solvent, and then 87.3 mmol of aqueous K2CO3 solution was added. The mixture was heated and stirred. At reflux, 1.3 mmol of Pd(PPh3)4 was added, and the mixture was heated and stirred for 6 hours. After the reaction was completed, the temperature was cooled to room temperature, and the K2CO3 solution was removed and filtered. The filtered solid was washed with ethanol to obtain product P-1.

[0128] MALDI-TOF: m / z: Calculated value: C 44 H 34 N4: 618.28, Measured value: 618.64.

[0129] Compound elemental analysis results: Calculated value: C 44 H 34 N4(%) : C, 85.41; H, 5.54; N, 9.05; Test value: C, 85.43; H, 5.54; N, 9.04.

[0130] Example 4: Synthesis of P-3

[0131]

[0132] The synthesis method of compound P-3 is similar to that of P-1, except that in step (3), C 19 was replaced with an equimolar amount of C3; in step (5), E1 was replaced with an equimolar amount of E3.

[0133] MALDI-TOF: m / z: Calculated value: C 44 H 34 N4: 618.28, Measured value: 618.50.

[0134] Compound elemental analysis results: Calculated value: C 44 H 34N4(%) : C, 85.41; H, 5.54; N, 9.05; Test value: C, 85.40; H, 5.55; N, 9.05.

[0135] Example 5: Synthesis of P-5

[0136]

[0137] The synthesis method of compound P-5 is similar to that of P-1, except that B in step (1) 19 is replaced by an equimolar amount of B5, and C in step (3) 19 is replaced by an equimolar amount of C3; E1 in step (5) is replaced by an equimolar amount of E5.

[0138] MALDI-TOF: m / z: Calculated value: C 44 H 34 N4: 618.28, Measured value: 618.45.

[0139] Compound elemental analysis results: Calculated value: C 44 H 34 N4(%) : C, 85.41; H, 5.54; N, 9.05; Test value: C, 85.39; H, 5.55; N, 9.05.

[0140] Example 6: Synthesis of P-7

[0141]

[0142] The synthesis method of compound P-7 is similar to that of P-1, except that E1 in step (5) is replaced by an equimolar amount of E7.

[0143] MALDI-TOF: m / z: Calculated value: C 45 H 35 N3: 617.28, Measured value: 617.63.

[0144] Compound elemental analysis results: Calculated value: C 45 H 35 N3(%) : C, 87.49; H, 5.71; N, 6.80; Test value: C, 87.47; H, 5.72; N, 6.80.

[0145] Example 7: Synthesis of P-9

[0146]

[0147] The synthesis method of compound P-9 is similar to that of P-1, except that E1 in reaction (5) is replaced with an equimolar amount of E9.

[0148] MALDI-TOF: m / z: calculated value: C 41 H 31 N3: 565.25, measured value: 565.71.

[0149] Elemental analysis results of the compound: calculated value: C 41 H 31 N3 (%) : C, 87.05; H, 5.52; N, 7.43; measured value: C, 87.07; H, 5.52; N, 7.42.

[0150] Example 8: Synthesis of P-11

[0151] This example provides a synthesis method of an organic compound, which includes the following steps:

[0152]

[0153] (1) Synthesis of P-11-1: Under an argon atmosphere, add 170 mmol of reactant A 11 , 57 mmol of Pd(OAc)2, 1.13 mmol of K2CO3, 205 mmol of reactant B2 and 341 mL of 1,4-dioxane to a 500 mL three-necked flask in sequence, and then heat, stir and reflux for about 24 hours. After cooling to room temperature, filter the reaction product through diatomaceous earth to separate the insoluble residue, add water, and separately take the organic layer. Add toluene to the aqueous layer and extract the organic layer again. Wash the organic layer thus collected with a saline solution and dry it over MgSO4. Separate MgSO4, concentrate the organic layer, and then separate the crude product thus obtained by silica gel column chromatography (using a mixture solvent of hexane and toluene as the eluent) to obtain intermediate P-11-1.

[0154] (2) Synthesis of P-11-2: Under an argon atmosphere, add 63 mmol of P-11-1, 126 mL of o-dichlorobenzene and 252 mmol of P(OEt)3 to a 300 mL three-necked flask in sequence, and then heat and stir at about 160 °C for about 24 hours. After cooling to room temperature, distill off the reaction solvent, and separate the crude product thus obtained by silica gel column chromatography (using a mixture solvent of hexane and toluene as the eluent) to obtain intermediate P-11-2.

[0155] (3) Synthesis of P-11-3: Under an argon atmosphere, 48.5 mmol of intermediate P-11-2, 1.5 mmol of Pd(dba)2, 121 mmol of NaOtBu, 242 mL of toluene, 48.5 mmol of reactant C 11 and 4.8 mmol of PtBu3 were sequentially added to a 500 mL three-necked flask, heated, stirred, and refluxed for about 6 hours. After cooling to room temperature, water was added to the reaction product, and the organic layer was separated separately. Toluene was added to the aqueous layer, and the organic layer was extracted again. The organic layer thus collected was washed with an aqueous saline solution and dried over MgSO4. The MgSO4 was separated, and the organic layer was concentrated, and then the crude product thus obtained was separated by silica gel column chromatography (using a mixed solvent of hexane and toluene as the eluent) to obtain intermediate P-11-3.

[0156] (4) Synthesis of P-11-4: Under an argon atmosphere, 120 mmol of magnesium turnings, 30 mmol of reactant D 11 , 3 g of iodine, and 20 mL of anhydrous tetrahydrofuran (THF) solvent were added to a 250 mL two-necked flask, heated and stirred to initiate the Grignard reaction. After initiation, a 100 mL anhydrous THF solution of 70 mmol of compound D 11 was added dropwise to the reaction solution, and the reaction was continued at 60 °C for 1 hour. The reaction solution was slowly transferred to a 500 mL three-necked flask containing 100 mmol of P-11-3 and 100 mL of anhydrous THF, and the reaction was carried out at room temperature for 12 hours. After cooling to room temperature, water was added to quench the reaction. Most of the solvent was removed by rotary evaporation of the reaction solution, and the residue was dissolved in dichloromethane and washed with water three times. The organic solution was collected, mixed with silica gel, and purified by column chromatography to obtain intermediate P-11-4.

[0157] (5) Synthesis of P-11-5: Under an argon stream, 43.6 mmol of reactant P-11-4 and 47.9 mmol of reactant E1 were dissolved in 150 mL of tetrahydrofuran (THF) solvent, and then an aqueous solution of 87.3 mmol of K2CO3 was added, and the mixture was heated and stirred. Under reflux, 1.3 mmol of Pd(PPh3)4 was added, and the mixture was heated and stirred for 6 hours. After the reaction was completed, the temperature was lowered to room temperature, and the K2CO3 solution was removed and filtered. The filtered solid was washed with ethanol to obtain product P-11-5.

[0158] (6) Synthesis of P-11: Under an argon stream, 43.6 mmol of reactant P-11-5 and 47.9 mmol of reactant F 11After dissolving in 150 mL of tetrahydrofuran (THF) solvent, 87.3 mmol of aqueous K2CO3 solution was added, and the mixture was heated and stirred. Under reflux conditions, 1.3 mmol of Pd(PPh3)4 was added, and the mixture was heated and stirred for 6 hours. After the reaction was completed, the temperature was cooled to room temperature, the K2CO3 solution was removed and filtered. The filtered solid was washed with ethanol to obtain product P-11.

[0159] MALDI-TOF: m / z: calculated value: C44H34N4: 618.28, measured value: 618.66.

[0160] Compound elemental analysis results: calculated value: C 41 H 31 N3 (%) : C, 85.41; H, 5.54; N, 9.05; measured value: C, 85.43; H, 5.53; N, 9.04.

[0161] The following application examples provide exemplary embodiments for illustrating the actual application of the organic optoelectronic compounds of the present application in OLED devices.

[0162] Application Example 1

[0163] This application example provides an OLED device, the structure of which is as Figure 1 shown, including 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 and a cover layer 10 stacked in sequence, Figure 1 The arrow in represents the light-emitting direction of the device.

[0164] The preparation method of the OLED device is as follows:

[0165] 1) Cut the glass substrate 1 into a size of 50 mm × 50 mm × 0.7 mm, ultrasonically treat it in isopropyl alcohol and deionized water for 30 min respectively, and then expose it to ozone for about 10 min for cleaning; mount the obtained glass substrate with the ITO anode 2 on a vacuum deposition device;

[0166] 2) On the ITO anode 2, deposit the hole buffer layer material HT-1∶HAT-CN by vacuum evaporation, and the mass ratio of the compound HT-1 to HAT-CN is 97:3 to obtain a layer with a thickness of 10 nm, and this layer serves as the first hole transport layer 3;

[0167] 3) Vacuum deposit the material HT-1 of the second hole transport layer 4 on the first hole transport layer 3 to obtain a layer with a thickness of 120 nm, and this layer serves as the second hole transport layer 4;

[0168] 4) Evaporate the material Prime-1 on the second hole transport layer 4 to obtain a layer with a thickness of 88 nm, which serves as the electron blocking layer 5;

[0169] 5) Co-deposit the light-emitting layer 6 on the electron blocking layer 5, where the organic compound K-2 provided in Example 1 of the present application is used as the host material, and Ir(MDQ)2(acac) is used as the doping material. The mass ratio of the organic compound K-2 to Ir(MDQ)2(acac) is 98:2, and the thickness is 45 nm;

[0170] 6) Vacuum evaporate the first electron transport layer 7 compound ET-1 on the light-emitting layer 6 to obtain the first electron transport layer 7 with a thickness of 30 nm;

[0171] 7) Vacuum evaporate the material LiF of the second electron transport layer 8 on the first electron transport layer 7 to obtain the second electron transport layer 8 with a thickness of 5 nm;

[0172] 8) Vacuum evaporate magnesium silver on the second electron transport layer 8 to prepare the cathode 9 with a thickness of 15 nm, where the mass ratio of Mg:Ag is 1:9;

[0173] 9) Vacuum evaporate the hole-type material CPL-1 with a high refractive index on the cathode 9, with a thickness of 70 nm, which is used as the covering layer 10.

[0174] The structural formulas of the materials HAT-CN, HT-1, Prime-1, Ir(MDQ)2(acac), ET-1, and CPL-1 mentioned in the above steps are shown as follows:

[0175]

[0176] Application Example 2

[0177] The difference between this application example and Application Example 1 is only that the organic compound K-2 in step (5) is replaced with an equal amount of the organic compound K-19 provided in Example 2 of the present application; other preparation steps are the same.

[0178] Application Example 3

[0179] The difference between this application example and Application Example 1 is only that the organic compound K-2 in step (5) is replaced with an equal amount of the organic compound P-1 provided in Example 3 of the present application; other preparation steps are the same.

[0180] Application Example 4

[0181] The difference between this application example and Application Example 1 is only that the organic compound K-2 in step (5) is replaced with an equal amount of the organic compound P-3 provided in Example 4 of the present application; other preparation steps are the same.

[0182] Application Example 5

[0183] The difference between this application example and Application Example 1 is only that the organic compound K-2 in step (5) is replaced with an equal amount of the organic compound P-5 provided in Example 5 of this application; other preparation steps are the same.

[0184] Application Example 6

[0185] The difference between this application example and Application Example 1 is only that the organic compound K-2 in step (5) is replaced with an equal amount of the organic compound P-7 provided in Example 6 of this application; other preparation steps are the same.

[0186] Application Example 7

[0187] The difference between this application example and Application Example 1 is only that the organic compound K-2 in step (5) is replaced with an equal amount of the organic compound P-9 provided in Example 7 of this application; other preparation steps are the same.

[0188] Application Example 8

[0189] The difference between this application example and Application Example 1 is only that the organic compound K-2 in step (5) is replaced with an equal amount of the organic compound P-11 provided in Example 8 of this application; other preparation steps are the same.

[0190] Application Comparative Example 1

[0191] The difference between this application comparative example and Application Example 1 is only that the organic compound K-2 in step (5) is replaced with an equal amount of the comparative compound Ref-1 (shown below); other preparation steps are the same.

[0192] Application Comparative Example 2

[0193] The difference between this application comparative example and Application Example 1 is only that the organic compound K-2 in step (5) is replaced with an equal amount of the comparative compound Ref-2 (shown below); other preparation steps are the same.

[0194]

[0195] Performance Evaluation of OLED Devices:

[0196] Use a Keithley 2365A digital nanovoltmeter to measure the current of the OLED device at different voltages, and then divide the current by the luminous area to obtain the current density of the OLED device at different voltages; use a Konica Minolta CS-2000 spectroradiance luminance meter to measure the luminance and radiant energy flux density of the OLED device at different voltages; according to the current density and luminance of the OLED device at different voltages, obtain at the same current density (10 mA / cm 2) of the turn-on voltage and current efficiency (CE, Cd / A), V on The brightness is 1Cd / m 2 The life span LT95 (at 50 mA / cm2) was obtained by measuring the time when the brightness of the OLED device reached 95% of the initial brightness. 2 The specific data are shown in Table 1.

[0197] Table 1

[0198] OLED Device Host Material <![CDATA[V on (V)]]> CE(Cd / A) LT95(h) Application Example 1 K-2 97.6％ 106.8％ 106.7％ Application Example 2 K-19 97.8％ 106.1％ 107.5％ Application Example 3 P-1 97.4％ 107.5％ 105.9％ Application Example 4 P-3 98.0％ 107.9％ 106.4％ Application Example 5 P-5 97.7％ 106.4％ 107.1％ Application Example 6 P-7 97.2％ 107.8％ 105.7％ Application Example 7 P-9 98.1％ 107.1％ 106.1％ Application Example 8 P-11 97.1％ 106.2％ 107.5％ Application Comparative Example 1 Ref-1 97.9％ 105.2％ 103.3％ Application Comparative Example 2 Ref-2 100％ 100％ 100％

[0199] As can be seen from Table 1, compared with OLED devices prepared with Ref-1 and Ref-2 as the main materials, the OLED devices prepared based on the organic compounds of the present application show excellent characteristics in terms of driving voltage, luminous efficiency and life. This is because the nitrogen atoms in the core part of the pyrrolopyrrole skeleton on the fused macrocycle of the present application improve the hole transport ability of the entire compound, which can improve the recombination probability of electrons and holes in the light-emitting layer in the organic electroluminescent device, improve the luminous efficiency, and the macrocycle has excellent thermal and charge tolerance, and can achieve a long life; the electron-withdrawing group is connected to one or both sides of the fused macrocycle, which can improve the electron transport ability of the entire compound, so that the entire molecule has bipolarity, and one side is connected to the adamantane structure with large steric hindrance, which will effectively reduce the dense packing of molecules, thereby reducing the quenching of excitons, improving the utilization rate of excitons, and effectively achieving the dispersion of excitons, thereby expected to improve the life and stability of the device. The comparative compound is similar in structure to the organic compound of the present application, but no electron-withdrawing group or adamantane group is connected.

[0200] It can be seen that even if the structure is similar, different types and positions of the connecting groups may cause changes in hole / electron injection, transmission characteristics, light efficiency characteristics, energy levels (HOMO, LUMO), and electronic balance between holes and electrons. The organic compound of the present application is more suitable as a host material than the comparative compound. Moreover, the enhanced stereoscopic properties of the molecular structure of the present application can also improve the solubility of the material, making it more possible to mass produce.

[0201] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present application, rather than to limit them; although the present application has been described in detail with reference to the foregoing embodiments, those of ordinary skill in the art should understand that they can still modify the technical solutions described in the foregoing embodiments, or perform equivalent replacements on some or all of the technical features; and these modifications or replacements do not make the essence of the corresponding technical solutions deviate from the scope of the technical solutions of the embodiments of the present application, and they should all be covered within the scope of the claims and the description of the present application. In particular, as long as there is no structural conflict, the technical features mentioned in each embodiment can be combined in any way. The present application is not limited to the specific embodiments disclosed in the text, but includes all technical solutions falling within the scope of the claims.

Claims

1. An OLED device, characterized in that, The OLED device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode. The organic thin film layer includes a light-emitting layer, and the material of the light-emitting layer includes an organic compound having a structure shown in Formula I below; wherein, R 1 and R 2 are independently selected from hydrogen, pyridyl, quinolinyl, isoquinolinyl, C6-C12 aryl-substituted benzopyridine, pyrazinyl, benzopyrazine, pyridazinyl, benzopyridazine, C6-C12 aryl-substituted benzopyrazine, imidazole, benzimidazole, C6-C12 aryl-substituted benzimidazole, pyrimidine, C6-C12 aryl-substituted pyrimidine, C6-C12 aryl-substituted benzopyrimidine, benzoxazole, benzothiazole, C6-C12 aryl-substituted benzothiazole, phenanthrolinyl, dibenzofuranyl, dibenzothiophenyl, diphenyltriazinyl, tripyridyl, phenyl and its cyano-substituted derivatives, biphenyl and its cyano-substituted derivatives, terphenyl and its cyano-substituted derivatives, naphthyl and its cyano-substituted derivatives, anthryl and its cyano-substituted derivatives, phenanthryl and its cyano-substituted derivatives, pyrenyl and its cyano-substituted derivatives, group and its cyano-substituted derivatives, fluorenyl and its cyano-substituted derivatives.

2. The OLED device according to claim 1, wherein, The organic compound is selected from any one of the compounds shown in Formula II or Formula III below: wherein, R 1 and R 2 are independently selected from hydrogen, pyridyl, quinolinyl, isoquinolinyl, C6-C12 aryl-substituted benzopyridine, pyrazinyl, benzopyrazine, pyridazinyl, benzopyridazine, C6-C12 aryl-substituted benzopyrazine, imidazole, benzimidazole, C6-C12 aryl-substituted benzimidazole, pyrimidine, C6-C12 aryl-substituted pyrimidine, C6-C12 aryl-substituted benzopyrimidine, benzoxazole, benzothiazole, C6-C12 aryl-substituted benzothiazole, phenanthrolinyl, dibenzofuranyl, dibenzothiophenyl, diphenyltriazinyl, tripyridyl, phenyl and its cyano-substituted derivatives, biphenyl and its cyano-substituted derivatives, terphenyl and its cyano-substituted derivatives, naphthyl and its cyano-substituted derivatives, anthracenyl and its cyano-substituted derivatives, phenanthryl and its cyano-substituted derivatives, pyrenyl and its cyano-substituted derivatives, and its cyano-substituted derivatives, fluorenyl and its cyano-substituted derivatives.

3. The OLED device according to claim 1, wherein The organic compound is selected from any one of the compounds shown in Formulas IV to VII below: Among them, R 1 , R 3 are each independently selected from hydrogen, pyridyl, quinolinyl, isoquinolinyl, C6-C12 aryl-substituted benzopyridine, pyrazinyl, benzopyrazine, pyridazinyl, benzopyridazine, C6-C12 aryl-substituted benzopyrazine, imidazole, benzimidazole, C6-C12 aryl-substituted benzimidazole, pyrimidine, C6-C12 aryl-substituted pyrimidine, C6-C12 aryl-substituted benzopyrimidine, benzoxazole, benzothiazole, C6-C12 aryl-substituted benzothiazole, phenanthrolinyl, dibenzofuranyl, dibenzothiophenyl, diphenyltriazinyl, tripyridyl, phenyl and its cyano-substituted derivatives, biphenyl and its cyano-substituted derivatives, terphenyl and its cyano-substituted derivatives, naphthyl and its cyano-substituted derivatives, anthryl and its cyano-substituted derivatives, phenanthryl and its cyano-substituted derivatives, pyrenyl and its cyano-substituted derivatives, group and its cyano-substituted derivatives and fluorenyl and its cyano-substituted derivatives, and one of them.

4. The OLED device according to any one of claims 1 to 2, characterized in that, R 1 、R 2 Each independently is one of hydrogen and the substituents represented by Formula A-1 to Formula A-20: Wherein, # represents a connection site.

5. The OLED device according to claim 3, wherein, R 1 、R 3 Each independently is hydrogen or one of the substituents represented by Formula A-1 to Formula A-20: Wherein, # represents a connection site.

6. An OLED device, characterized in that, The OLED device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode. The organic thin film layer includes a light-emitting layer, and the material of the light-emitting layer includes an organic compound having a structure shown in Formula I below; wherein, R 1 , R 2 are each independently one of hydrogen and the substituents represented by Formula E-1 to Formula E-54: Wherein, # represents a connection site.

7. An OLED device, characterized in that, The OLED device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode. The organic thin film layer includes a light-emitting layer, and the material of the light-emitting layer includes an organic compound. The organic compound is selected from any one of the compounds shown in Formulas IV to VII below: wherein, R 1 , R 3 each independently represents hydrogen or one of the substituents represented by Formula E-1 to Formula E-54: Wherein, # represents a connection site.

8. The OLED device according to any one of claims 1 to 2, characterized in that, The R 1 and the R 2 are the same substituents.

9. An OLED device, characterized in that, The OLED device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode. The organic thin film layer includes a light-emitting layer, and the material of the light-emitting layer includes an organic compound. The organic compound is selected from any one of the compounds shown in Formulas D-1 to D-33 below:

10. An OLED device, characterized in that, The OLED device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode. The organic thin film layer includes a light-emitting layer, and the material of the light-emitting layer includes an organic compound. The organic compound is selected from any one of the compounds shown in Formulas K-1 to K-36 below:

11. The OLED device according to any one of claims 1 to 2, characterized in that, The R 1 and the R 2 are different substituents.

12. An OLED device, characterized in that, The OLED device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode. The organic thin film layer includes a light-emitting layer, and the material of the light-emitting layer includes an organic compound having a structure shown in Formula I below; Wherein, the R 1 and the R 2 one of them is hydrogen, and the other is one of Formula A-1 to A-20 or one of Formula E-1 to E-54; Wherein, # represents a connection site.

13. An OLED device, characterized in that, The OLED device includes an anode, a cathode, and an organic thin film layer disposed between the anode and the cathode. The organic thin film layer includes a light-emitting layer, and the material of the light-emitting layer includes an organic compound. The organic compound is selected from any one of the compounds shown in Formulas P-1 to P-83 below:

14. A display panel, characterized in that, The display panel includes the OLED device according to any one of claims 1 to 13.

15. A display device, characterized in that, A display panel including the display panel according to claim 14.

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