Organic compounds, OLED devices and display panels

Abstract

The application provides an organic compound, an OLED device and a display panel. The organic compound provided by the application introduces a larger conjugated structure containing a nitrogen atom, and the lone pair electrons in the nitrogen atom are conjugated to a benzene ring. The structure formed by the seven-membered nitrogen-containing heterocycle and the large conjugated system generally has good stability, and the hole transport effect is obviously strengthened, which is related to the electronic structure distribution of the seven-membered nitrogen-containing heterocycle. The lone pair electrons of the N atom participate in the construction of the large conjugated system, so that the transmission is more matched. By introducing the seven-membered nitrogen-containing heterocycle in the conjugated system, the charge transport of the molecule can be more balanced, the stability of the host material can be improved, and the light-emitting device prepared therefrom can greatly improve the carrier transport efficiency of the device, and then improve the efficiency and service life of the device.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of organic light-emitting, in particular to an organic compound, an OLED device and a display panel. BACKGROUND

[0002] Organic light-emitting device (OLED) as a new generation of display technology has the advantages of self-luminescence, wide viewing angle, high contrast, low energy consumption, fast response, etc., and has been widely used in display field.

[0003] OLED includes cathode, anode and organic thin film layer, wherein the organic thin film layer contains light-emitting material, the cathode and the anode inject electrons and holes into the organic thin film layer respectively, and the electrons and holes combine in the light-emitting material to generate electron-hole pairs, i.e. excitons. The excitons can release energy in the form of light in the process of returning from the excited state to the stable ground state, thereby emitting visible light. Therefore, in OLED, different light-emitting materials can be selected to produce different colors of visible light to meet the full color requirement.

[0004] The currently reported red light host is usually a large conjugated aromatic ring, which usually shows low device efficiency and poor stability in devices. SUMMARY

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

[0006] In a first aspect, the present application provides an organic compound having a structural formula as shown in formula I:

[0007]

[0008] wherein A, B, C, D, E are each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, A and B are bonded to form a ring or A and B are not bonded to form a ring; L is selected from any one of single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 cycloalkylene.

[0009] In a second aspect, the present application provides an OLED device, which comprises an anode, a cathode and an organic thin film layer arranged between the anode and the cathode, and the material of the organic thin film layer comprises the above-mentioned organic compound.

[0010] In a third aspect, the present application provides a display panel, which comprises the above-mentioned OLED device.

[0011] Compared with the prior art, the present application has at least the following beneficial effects:

[0012] The organic compound of the technical solution of the present application introduces a larger conjugated structure containing a nitrogen atom, and at the same time, the lone pair of electrons in the nitrogen atom is conjugated into the benzene ring. The structure formed by the seven-membered nitrogen-containing heterocycle and the large conjugated system usually has good stability, and the hole transport effect will be obviously enhanced, which is related to the electronic structure distribution of the seven-membered nitrogen-containing heterocycle. The lone pair of electrons of the N atom participates in the construction of the large conjugated system, so that the charge transport of the molecule is more balanced, the stability of the host material is improved, and the light-emitting device prepared therefrom greatly improves the carrier transport efficiency of the device, and further improves the efficiency and service life of the device. BRIEF DESCRIPTION OF DRAWINGS

[0013] In order to more clearly illustrate the technical solutions of the embodiments of the present application, the drawings required to be used in the embodiments of the present application will be briefly introduced as follows. Obviously, the drawings described below are only some embodiments of the present application, and other drawings can be obtained by those skilled in the art without creating any creative labor.

[0014] Figure 1 The structural schematic diagram of the OLED device provided by some embodiments of the present application is shown. DETAILED DESCRIPTION

[0015] In order to make the purposes, technical solutions and beneficial technical effects of the present application clearer, the present application will be further described in detail in combination with the embodiments. It should be understood that the embodiments described in the specification are only for the purpose of explaining the present application, and are not intended to limit the present application.

[0016] The above summary of the present application is not intended to describe each disclosed embodiment or each implementation in the present application. The following description illustrates the exemplary embodiments more specifically. In many places throughout the application, guidance is provided by a series of embodiments, which can be used in various combinations. In each example, the enumeration is only representative of a group, and should not be interpreted as exhaustive.

[0017] In the description herein, unless otherwise specified, "above", "below" include the number, and the meaning of "more than one", "one or more" is two (one) or more.

[0018] The terms "a", "the" refer to one or more molecules of the compound, rather than limiting to a single molecule of the compound. In addition, one or more molecules can be the same or can not be the same, as long as they belong to the category of the chemical compound.

[0019] The terms "comprise" and variations thereof, when used in the specification and in claims, do not exclude other steps or elements.

[0020] The terms "preferably," "more preferably" and "most preferably" and variations thereof in the specification and claims are used to indicate a desired property, but do not limit the scope of the application. The terms "preferred" and "preferably" are used to indicate that a feature, an embodiment, or an example is, for certain reasons, advantageous. However, other embodiments can be preferred depending on the circumstances. Furthermore, the description herein does not specify a single preferred embodiment of the application, and as such, there are a number of preferred aspects and embodiments that satisfy the terms of the claims and the description herein.

[0021] Groupings of alternative elements or embodiments of the application disclosed herein are not to be construed as limitations. Each group member can be used independently and the grouping can be used in any combination with other group members or with other elements found in the disclosure. It is anticipated that one or more members of a group can also be included in or deleted from a group for reasons of convenience and / or patentability. When any such inclusion or deletion occurs, the specification is herein deemed to contain the altered group for the purpose of interpreting the meaning of the specification and the interpretation of the specification will pertain to the properly amended claims.

[0022] Unless otherwise indicated, when a compound or chemical structural feature (e.g., aryl) is referred to as "substituted" the feature can have one or more substituents. The term "substituents" has the broadest meaning known to one of ordinary skill in the art and includes moieties that occupy a position normally occupied by one or more hydrogen atoms attached to a parent compound or chemical structural feature.

[0023] The term "aryl" refers to a closed aromatic ring or ring system. Examples of aryl groups include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, biphenyl (including di-phenyl, tri-phenyl), triphenylenyl, pyrenyl, spirobifluorenyl, In various embodiments, a C6-C30 aryl group, i.e., aryl, can contain from 6 to 30 carbon atoms used to form the ring.

[0024] The term "heteroaryl" refers to one or more atoms in the ring of an aryl group that are an element other than carbon. In some embodiments, a C5-C30 heteroaryl group can contain from 5 to 25, 5 to 18, or 6 to 12 ring heteroatoms (e.g., N, O, etc.) throughout the molecule. Examples of heteroaryl groups include, but are not limited to, pyrrolyl, furanyl, oxazolyl, isoxazolyl, thienyl, thiazolyl, isothiazolyl, thiadiazolyl, oxadiazolyl, imidazolyl, pyrazolyl, triazolyl, pyridazinyl, pyrazinyl, pyridyl, pyrimidinyl, triazinyl, indolyl, quinolinyl, isoquinolinyl, acridinyl, purinyl, pteridinyl, benzofuranyl, benzothienyl, benzimidazolyl, benzothiazolyl, benzotriazolyl, benzoxadiazolyl, benzoxazolyl, cinnoline, quinoxalinyl, dibenzofuranyl, dibenzothienyl, carbazolyl, phenanthrolinyl, indolizinyl, naphthridinyl, and phthalazinyl. In various embodiments, a C5-C30 heteroaryl group, i.e., a heteroaryl group, can contain from 5 to 30 carbon atoms used to form the ring.

[0025] In the present text, the representation of a single bond through a ring or ring system means that the single bond can be attached at any accessible position of the ring or ring system.

[0026] Currently, the light-emitting layer of OLED devices generally uses a host material / dopant mixed system as the light-emitting material, which can improve color purity, light-emitting efficiency, and stability. Generally, using a host material / dopant system, the selection of the host material is crucial because the host material greatly affects the efficiency and stability of the OLED device. The preferred host material should have a suitable molecular weight to be deposited under vacuum, and at the same time, it also needs to have a high glass transition temperature and thermal decomposition temperature to ensure thermal stability, high electrochemical stability to ensure long service life, easy to form an amorphous thin film, and good interface with adjacent functional layer materials, and not prone to molecular movement. Especially as a red light host material, the material is required to have good carrier transport capacity and a suitable triplet energy level to ensure that the energy can be effectively transferred to the guest material in the light-emitting process, thereby achieving high efficiency.

[0027] However, the inventors of the present application have noticed that the red light host reported in the prior art is generally a large conjugated system aromatic ring. Due to the low triplet energy level brought by the large conjugated structure, the excimer energy cannot be effectively transferred to the guest, and at the same time, the balance problem of the carrier transport of the host material in the device is ignored, which leads to the problem of low efficiency and poor stability of the organic compound in the device.

[0028] In view of the above problems, the inventors of the present application have studied and provided an organic compound which can significantly improve the efficiency of the device and solve the problems of efficiency and service life of the existing OLED.

[0029] Organic compound

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

[0031]

[0032] wherein A, B, C, D, E are each independently selected from substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, A and B are bonded to form a ring or A and B are not bonded to form a ring; L is selected from any one of a single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene, substituted or unsubstituted C3-C30 cycloalkylene.

[0033] In the embodiments of the present application, A, B, C, D and their adjacent structures are fused to form a fused ring compound.

[0034] In the embodiments of the present application, C6-C30 can each 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.

[0035] In the embodiments of the present application, C3-C30 can each 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.

[0036] In the embodiments of the present application, C2-C30 can each independently be C2, 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.

[0037] each of the substituents in the substituted aryl, the substituted arylhetero, the substituted arylene, the substituted heteroarylene, the substituted cycloalkyl is independently selected from any one of deuterium, halogen, cyano, C1-C10 (e.g., can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.) straight chain or branched alkyl, C1-C10 (e.g., can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.) alkoxy, C1-C10 (e.g., can be C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, etc.) alkylthio, C6-C20 (e.g., can be C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.) aryl, C2-C20 (e.g., can be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.) heteroaryl, or C6-C18 (e.g., can be C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, etc.) arylamino.

[0038] The organic compound in the embodiments of the present application introduces a larger conjugated structure containing a nitrogen atom, and at the same time, conjugates the lone pair of electrons in the nitrogen atom into a benzene ring. The structure formed by the seven-membered nitrogen-containing heterocycle and the large conjugated system generally has good stability, and the hole transport effect is obviously enhanced, which is related to the electronic structure distribution of the seven-membered nitrogen-containing heterocycle. The lone pair of electrons of the N atom participates in the construction of the large conjugated system, so that the transmission is more matched. By introducing a seven-membered nitrogen-containing heterocycle in the conjugated system, the charge transmission of the molecule can be more balanced, and the stability of the host material can be improved. The light-emitting device prepared therefrom greatly improves the carrier transport efficiency of the device, and further improves the efficiency and service life of the device.

[0039] The organic compound in the embodiments of the present application can be used as a light-emitting layer material. By cooperating with other suitable materials, the light-emitting efficiency and service life of the electroluminescent device can be improved, and a solution for preparing a light-emitting device with low manufacturing cost, high efficiency and long service life is provided.

[0040] In some embodiments, A, B, C, D are each independently selected from unsubstituted or Ry1-substituted phenyl, unsubstituted or Ry1-substituted naphthyl, unsubstituted or Ry1-substituted pyridyl, unsubstituted or Ry1-substituted furanyl, unsubstituted or Ry1-substituted thienyl; Ry1is selected from any one of C6-C20 aryl or C2-C20 heteroaryl.

[0041] Ry1is selected from any of C6-C20 (e.g., can be C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.) aryl or C2-C20 (e.g., can be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.) heteroaryl.

[0042] Exemplarily, A, B and C are phenyl, and D is pyridyl.

[0043] In some embodiments, the organic compound is selected from any of the following compounds shown in Formula 1 to Formula 8:

[0044]

[0045]

[0046] wherein G, J, K, M are each independently null or selected from substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C3-C24 heteroaryl.

[0047] In some embodiments, G, J, K, M are fused with their adjacent structures to form a fused ring compound.

[0048] In some embodiments, the organic compound is selected from any of the following compounds shown in Formula 1-1 to Formula 1-8:

[0049]

[0050] In some embodiments, the organic compound is selected from any of the following compounds shown in Formula 2-1 to Formula 2-8:

[0051]

[0052] In some embodiments, the organic compound is selected from any of the following compounds shown in Formula 3-1 to Formula 3-8:

[0053]

[0054] wherein G, J, K, M are each independently null or selected from substituted or unsubstituted C6-C24 aryl, substituted or unsubstituted C3-C24 heteroaryl.

[0055] In some embodiments, G, J, K, M are fused with their adjacent structures to form a fused ring compound.

[0056] In some embodiments, the organic compound is selected from any one of the following compounds shown in Formulae 4-1 to 4-16:

[0057]

[0058] In some embodiments, aryl is independently selected at each occurrence from any one of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, 9,9'-dimethylfluorenyl, 9,9'-diphenylfluorenyl, or spirobifluorenyl.

[0059] In some embodiments, heteroaryl is independently selected at each occurrence from any one of carbazolyl, triazinyl, pyridyl, pyrimidinyl, imidazolyl, oxazolyl, thiazolyl, pyranyl, thiazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, dibenzothiophenyl, dibenzofuranyl, naphthoimidazolyl, naphthoxazolyl, naphthothiazolyl, phenanthroimidazolyl, phenanthrooxazolyl, phenanthrothiazolyl, quinoxalinyl, quinazolinyl, indolocarbazolyl, indolofluorenyl, benzothienopyrazinyl, benzothienopyrimidinyl, benzofuranopyrazinyl, benzofuranopyrimidinyl, benzofuranocarbazolyl, benzothienocarbazolyl, indolopyrazinyl, indolopyrimidinyl, indenopyrazinyl, or indenopyrimidinyl.

[0060] In some embodiments, G, J, K, M are each independently selected from null, unsubstituted or Ry2-substituted phenyl, unsubstituted or Ry2-substituted pyridyl, unsubstituted or Ry2-substituted furanyl; unsubstituted or Ry2-substituted thienyl;

[0061] Ry2is selected from any one of C6-C20 aryl or C2-C20 heteroaryl.

[0062] Ry2is selected from any one of C6-C20 (e.g., can be C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.) aryl or C2-C20 (e.g., can be C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, etc.) heteroaryl.

[0063] In some embodiments, L is selected from any one of single bond, phenylene, biphenylene, naphthylene, or C3-C12 nitrogen-containing heteroarylene.

[0064] In some embodiments, E is selected from any one of the following structural formulae shown in T-1 to T-14:

[0065]

[0066]

[0067] wherein the dotted line indicates the connecting position of the group;

[0068] R t1 is selected from any one of C6-C20 aryl, C2-C20 heteroaryl.

[0069] The organic compound provided in the present application uses a large conjugated aromatic system to connect aza electron-withdrawing structural unit, which can significantly improve the device efficiency. In combination with a suitable p-type material, the carrier transport balance can be further improved, thereby solving the problems of efficiency and lifetime of the existing OLED.

[0070] In some embodiments, E is selected from any one of the structural formulae t-1 to t-28 shown below:

[0071]

[0072]

[0073] wherein the dotted line indicates the connecting position of the group.

[0074] In some embodiments, the organic compound is selected from any one of the compounds shown in U-1 to U-54 below:

[0075]

[0076]

[0077]

[0078]

[0079] OLED device

[0080] In a second aspect, the embodiments of the present application provide 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 organic compound described above. The material of the organic thin film layer can be one of the organic compounds described above, or can include a mixture of two or more of the organic compounds described above.

[0081] In some embodiments, the anode material can include metals (e.g., copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, and the like, and alloys thereof), metal oxides (e.g., indium oxide, zinc oxide, indium tin oxide (ITO), indium zinc oxide (IZO), and the like), conductive polymers (e.g., polyaniline, polypyrrole, poly(3-methylthiophene), and the like). In addition to the above materials and combinations thereof that facilitate hole injection, other known materials suitable for anodes can also be included.

[0082] In some embodiments, the cathode can include a metal layer (e.g., aluminum, magnesium, silver, indium, tin, titanium, etc., and alloys thereof), a multi-layer cathode (e.g., LiF / Al, LiO2 / Al, BaF2 / Al, etc.) composed of a metal layer and a layer containing one or more of a metal oxide and a metal halide. In addition to the above materials and combinations thereof that facilitate electron injection, other known materials suitable for use as a cathode are also included.

[0083] In some embodiments of the present application, the organic thin film layer further comprises an electron transport region and / or a hole transport region, wherein the electron transport region and the hole transport region comprise one or more of the organic compounds of any of the embodiments described above.

[0084] In embodiments of the present application, the electron transport region refers to a region in which electrons move between the cathode and the light-emitting layer. Illustratively, the electron transport region can include at least one layer of an electron injection layer, an electron transport layer, and a hole blocking layer, and at least one layer includes one or more of the organic compounds of any of the embodiments described above.

[0085] Illustratively, the electron transport region includes a first electron transport layer and a second electron transport layer stacked together, and the materials of the first electron transport layer and the second electron transport layer include one or more of the organic compounds of any of the embodiments described above.

[0086] The hole transport region refers to a region in which holes move between the anode and the light-emitting layer. Illustratively, the hole transport region can include at least one layer of a hole injection layer, a hole transport layer, and an electron blocking layer, and at least one layer includes one or more of the organic compounds of any of the embodiments described above.

[0087] Illustratively, the hole transport region includes a first hole transport layer, a second hole transport layer, and an electron blocking layer stacked together, 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 of any of the embodiments described above.

[0088] The OLED device can be fabricated using methods known in the art. Illustrative fabrication methods include forming an anode on a transparent or non-transparent smooth substrate, forming a multi-layer organic thin film layer on the anode, and forming a cathode on the organic thin film layer. The organic thin film layer can be formed using known film formation methods such as evaporation, sputtering, spin coating, dipping, ion plating, etc.

[0089] Figure 1 An OLED device 10 is shown as an example, which includes a glass substrate 11, an ITO anode 12, a hole injection layer 13, a first hole transport layer 14, a second hole transport layer 15, a light-emitting layer 16, an electron transport layer 17, and a cathode 18 stacked in order.

[0090] Display panel

[0091] The embodiment of the present application provides a display panel, and the display panel comprises the OLED device.

[0092] The display panel of the present application contains 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, and does not use expensive noble metals and the like, and has the advantages of low cost and the like.

[0093] The display panel can be used in a display device, and the display device can be, but is not limited to, a smartphone, a smartwatch, a tablet computer, a notebook computer, a PC, a TV, or a display device for a vehicle, a VR, an AR helmet, or a lighting device, and the like, and the present application does not specifically limit this.

[0094] The following examples more specifically describe the present disclosure, which are merely illustrative and not restrictive, because various modifications and changes within the scope of the present disclosure will be apparent to those skilled in the art. Unless otherwise stated, all parts, percentages, and ratios reported in the following examples are by weight, and all reagents used in the examples are commercially available or synthesized according to conventional methods and used directly without further purification, and the instruments used in the examples are commercially available.

[0095] Synthesis of organic compounds

[0096] The present application exemplarily provides several preparation methods of organic compounds. Other compounds of the present application can be prepared according to the exemplary methods. According to the exemplary compound preparation methods, those skilled in the art can easily obtain specific methods for realizing each synthesis step from relevant scientific literature or standard textbooks in the art. Unless specifically indicated, commercially available or known compounds in the literature are used as starting materials for synthesis. Those skilled in the art of organic synthesis will recognize that the nature and order of the synthetic steps can be varied for the purpose of optimizing the generation of the compounds described herein.

[0097] The processes described herein can be monitored according to any suitable method known in the art. For example, product generation 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-Vis), 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] Example 1: Synthesis of U-10

[0099] The present embodiment provides a synthesis method of an organic compound, comprising the following steps:

[0100]

[0101] (1) Synthesis of U-10-1: Under a nitrogen atmosphere, raw material A 10 (25 g), raw material B 10 (38 g), tetrakis(triphenylphosphine)palladium (0.8 g) and X-phos (0.8 g) were sequentially added to a 1000 mL three-necked flask, then 500 mL of dry toluene was injected into the flask and vacuumed, replaced with nitrogen for three times, heated to 110°C to reflux for 10 hours, after the reaction was completed, the reaction mixture was poured into 500 mL of deionized water and stirred rapidly, during which the product was continuously precipitated, after vacuum filtration, the product was dissolved with dichloromethane again and extracted with saturated brine three times, the organic phase was combined and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:18) to obtain 33.1 g of intermediate U-10-1, with a yield of 80.5%.

[0102] (2) Synthesis of U-10-2: Under a nitrogen atmosphere, intermediate U-10-1 (24.6 g) and sodium tert-butoxide (44 g) were sequentially added to a 500 mL three-necked flask, then 220 mL of dry toluene was injected into the flask and vacuumed, replaced with nitrogen for three times, heated to 110°C to reflux for 10 hours, after the reaction was completed, the reaction mixture was poured into 500 mL of deionized water and stirred rapidly, during which the product was continuously precipitated, after vacuum filtration, the product was dissolved with dichloromethane again and extracted with saturated brine three times, the organic phase was combined and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:15) to obtain 16.0 g of intermediate U-10-2, with a yield of 68.2%.

[0103] (3) Synthesis of U-10-3: Under a nitrogen atmosphere, compound U-10-2 (11 g), bis(tricyclohexylphosphine)palladium dichloride (0.6 g) and cesium carbonate (22 g) were sequentially added to a 500 mL three-necked flask, then 200 mL of dry dimethylacetamide and 12 mL of tert-pentanoic acid were injected into the flask and vacuumed, replaced with nitrogen for three times, heated to 170°C to reflux for 8 h, after the reaction was completed, the reaction mixture was poured into 500 mL of deionized water and stirred rapidly, during which the product was continuously precipitated, vacuum filtration was performed with a Buchner funnel, the filter cake was dissolved with dichloromethane and extracted with saturated brine three times, the organic phase was combined and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:10) to obtain 6.2 g of compound U-10-3, with a yield of 62.5%.

[0104] (4) Synthesis of U-10: Under a nitrogen atmosphere, intermediate U-10-3 (8.9 g), raw material C 10(9.8 g), palladium trifluoroacetate (0.35 g) and cesium carbonate (12 g) were sequentially added into a 500 mL three-necked flask, then 200 mL dry toluene was injected into the flask and vacuumed and replaced by nitrogen for three times, heated to 110 °C and refluxed for 10 hours. After the reaction was completed, the reaction mixture was poured into 500 mL deionized water and stirred rapidly, during which the product was precipitated continuously. After filtration, the product was dissolved in dichloromethane again and extracted with saturated brine for three times. The combined organic phase was separated and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:10) to obtain 10.5 g of solid powder, which was compound U-10, with a yield of 63.5%.

[0105] MALDI-TOF: m / z: calculated for C 47 H 27 N5: 661.23, found: 661.13. Compound elemental analysis results: C, 85.30; H, 4.11; N, 10.58.

[0106] Example 2: Synthesis of U-36

[0107] The embodiment provides a synthesis method of an organic compound, and comprises the following steps.

[0108]

[0109] (1) Synthesis of U-36-1: under a nitrogen environment, raw material A 10 (25 g), raw material B 36 (42 g), tetrakis(triphenylphosphine)palladium (0.8 g) and X-phos (0.8 g) were sequentially added into a 1000 mL three-necked flask, then 500 mL dry toluene was injected into the flask and vacuumed and replaced by nitrogen for three times, heated to 110 °C and refluxed for 10 hours. After the reaction was completed, the reaction mixture was poured into 500 mL deionized water and stirred rapidly, during which the product was precipitated continuously. After filtration, the product was dissolved in dichloromethane again and extracted with saturated brine for three times. The combined organic phase was separated and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:18) to obtain 38.1 g of intermediate U-36-1, with a yield of 82.6%.

[0110] (2) Synthesis of U-36-2: Intermediate U-36-1 (27.7 g) and sodium tert-butoxide (44 g) were sequentially added to a 500 mL three-necked flask under nitrogen atmosphere, then 220 mL of dry toluene was injected into the flask and vacuumed, replaced with nitrogen for three times, heated to 110 °C and refluxed for 10 hours. After the reaction was completed, the reaction mixture was poured into 500 mL of deionized water and stirred rapidly, during which the product precipitated continuously. After filtration, the product was dissolved in dichloromethane and extracted with saturated brine three times. The combined organic phase was separated and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:15) to obtain 17.4 g of intermediate U-36-2, with a yield of 65.8%.

[0111] (3) Synthesis of U-36-3: Compound U-36-2 (12.4 g), bis(tricyclohexylphosphine)palladium dichloride (0.6 g) and cesium carbonate (22 g) were sequentially added to a 500 mL three-necked flask under nitrogen atmosphere, then 200 mL of dry dimethylacetamide and 12 mL of tert-pentanoic acid were injected into the flask and vacuumed, replaced with nitrogen for three times, heated to 170 °C and refluxed for 8 hours. After the reaction was completed, the reaction mixture was poured into 500 mL of deionized water and stirred rapidly, during which the product precipitated continuously. After filtration with a Buchner funnel, the filter cake was dissolved in dichloromethane and extracted with saturated brine three times. The combined organic phase was separated and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:10) to obtain 6.6 g of compound U-36-3, with a yield of 58.4%.

[0112] (4) Synthesis of U-36: Intermediate U-36-3 (10.2 g), raw material C 36 (9.1 g), palladium trifluoroacetate (0.35 g) and cesium carbonate (12 g) were sequentially added to a 500 mL three-necked flask under nitrogen atmosphere, then 200 mL of dry toluene was injected into the flask and vacuumed, replaced with nitrogen for three times, heated to 110 °C and refluxed for 10 hours. After the reaction was completed, the reaction mixture was poured into 500 mL of deionized water and stirred rapidly, during which the product precipitated continuously. After filtration, the product was dissolved in dichloromethane and extracted with saturated brine three times. The combined organic phase was separated and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:10) to obtain 11.5 g of solid powder, which was compound U-36, with a yield of 66.8%.

[0113] MALDI-TOF: m / z: calculated for C 51 H 29 N5: 684.23, found: 684.15. Compound elemental analysis results: C, 87.68; H, 4.12; N, 8.18.

[0114] Example 3: Synthesis of U-40

[0115] The embodiment provides a synthesis method of an organic compound, and comprises the following steps:

[0116]

[0117] The synthesis method of the compound U-40 is similar to that of the compound U-36, except that step (4) is the synthesis of the compound U-40: under the nitrogen environment, intermediate U-36-3 (10.2 g), raw material C 10 (9.8 g), palladium trifluoroacetate (0.35 g) and cesium carbonate (12 g) are sequentially added into a 500 mL three-necked flask, then 200 mL dry toluene is injected into the flask and vacuumized and replaced by nitrogen for three times, heating to 110 DEG C to reflux for 10 hours, after the reaction is completed, the reaction mixture is poured into 500 mL deionized water and rapidly stirred, and the product is continuously precipitated during the period, after filtration, the product is dissolved with dichloromethane again and extracted with saturated brine for three times, the organic phase is combined and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:10), 12.5 g of solid powder is obtained, which is the compound U-40, and the yield is 69.6%.

[0118] MALDI-TOF: m / z: calculated value: C 51 H 29 N5:711.24, actual value: 711.33. Compound elemental analysis results: C, 86.05; H, 4.10; N, 9.83.

[0119] Example 4: Synthesis of U-45

[0120] The embodiment provides a synthesis method of an organic compound, and comprises the following steps:

[0121]

[0122] (1) Synthesis of U-45-1: under the nitrogen environment, raw material A 45 (30 g), raw material B 36 (42 g), tetrakis(triphenylphosphine)palladium (0.8 g) and X-phos (0.8 g) are sequentially added into a 1000 mL three-necked flask, then 500 mL dry toluene is injected into the flask and vacuumized and replaced by nitrogen for three times, heating to 110 DEG C to reflux for 10 hours, after the reaction is completed, the reaction mixture is poured into 500 mL deionized water and rapidly stirred, and the product is continuously precipitated during the period, after filtration, the product is dissolved with dichloromethane again and extracted with saturated brine for three times, the organic phase is combined and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:15), 40.9 g of intermediate U-45-1 is obtained, and the yield is 80.2%.

[0123] (2) Synthesis of U-45-2: Intermediate U-45-1 (30.7 g) and sodium tert-butoxide (44 g) were sequentially added to a 500 mL three-necked flask under nitrogen atmosphere, then 220 mL of dry toluene was injected into the flask and vacuumed, replaced by nitrogen for three times, heated to 110 °C and refluxed for 10 hours. After the reaction was completed, the reaction mixture was poured into 500 mL of deionized water and stirred rapidly, during which the product precipitated continuously. After filtration, the product was dissolved in dichloromethane and extracted with saturated brine three times. The combined organic phase was separated and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:12) to obtain 17.7 g of intermediate U-45-2, with a yield of 60.1%.

[0124] (3) Synthesis of U-45-3: Compound U-45-2 (13.7 g), bis(tricyclohexylphosphine)palladium dichloride (0.6 g) and cesium carbonate (22 g) were sequentially added to a 500 mL three-necked flask under nitrogen atmosphere, then 200 mL of dry dimethylacetamide and 12 mL of tert-pentanoic acid were injected into the flask and vacuumed, replaced by nitrogen for three times, heated to 170 °C and refluxed for 8 hours. After the reaction was completed, the reaction mixture was poured into 500 mL of deionized water and stirred rapidly, during which the product precipitated continuously. After filtration with a Buchner funnel, the filter cake was dissolved in dichloromethane and extracted with saturated brine three times. The combined organic phase was separated and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:8) to obtain 6.4 g of compound U-45-3, with a yield of 50.1%.

[0125] (4) Synthesis of U-45: Intermediate U-45-3 (11.5 g), raw material C 10 (9.8 g), palladium trifluoroacetate (0.35 g) and cesium carbonate (12 g) were sequentially added to a 500 mL three-necked flask under nitrogen atmosphere, then 200 mL of dry toluene was injected into the flask and vacuumed, replaced by nitrogen for three times, heated to 110 °C and refluxed for 10 hours. After the reaction was completed, the reaction mixture was poured into 500 mL of deionized water and stirred rapidly, during which the product precipitated continuously. After filtration, the product was dissolved in dichloromethane and extracted with saturated brine three times. The combined organic phase was separated and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:8) to obtain 9.9 g of solid powder, which was compound U-45, with a yield of 51.6%.

[0126] MALDI-TOF: m / z: calculated for C 55 H 31 N5: 761.25, found: 761.17. Compound elemental analysis results: C, 86.68; H, 4.10; N, 9.19.

[0127] Example 5: Synthesis of U-46

[0128] The embodiment provides a synthesis method of an organic compound, and comprises the following steps:

[0129]

[0130] The synthesis method of the compound U-46 is similar to that of the compound U-10, except that the step (4) is the synthesis of the compound U-46: under the nitrogen environment, the intermediate 4-3 (8.9 g), the raw material C 46 (8.5 g), palladium trifluoroacetate (0.35 g) and cesium carbonate (12 g) are sequentially added into a 500 mL three-necked flask, then 200 mL dry toluene is injected into the flask and replaced by nitrogen for three times, heating to 110 DEG C to reflux for 10 hours, after the reaction is completed, the reaction mixture is poured into 500 mL deionized water and stirred rapidly, and the product is precipitated during the stirring, after filtration, the product is dissolved by dichloromethane and extracted by saturated brine for three times, the organic phase is combined and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:10), and 9.4 g solid powder is obtained, which is the compound U-46, and the yield is 61.2%.

[0131] MALDI-TOF: m / z: calculated value: C 44 H 24 N4: 608.20, measured value: 608.11. Compound elemental analysis results: C, 86.80; H, 3.95; N, 9.20.

[0132] Example 6: Synthesis of U-48

[0133] The embodiment provides a synthesis method of an organic compound, and comprises the following steps:

[0134]

[0135] The synthesis method of the compound U-48 is similar to that of the compound U-45, except that the step (4) is the synthesis of the compound U-46: under the nitrogen environment, the intermediate U-45-3 (11.5 g), the raw material C 36 (9.1 g), palladium trifluoroacetate (0.35 g) and cesium carbonate (12 g) are sequentially added into a 500 mL three-necked flask, then 200 mL dry toluene is injected into the flask and replaced by nitrogen for three times, heating to 110 DEG C to reflux for 10 hours, after the reaction is completed, the reaction mixture is poured into 500 mL deionized water and stirred rapidly, and the product is precipitated during the stirring, after filtration, the product is dissolved by dichloromethane and extracted by saturated brine for three times, the organic phase is combined and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:8), and 9.9 g solid powder is obtained, which is the compound U-48, and the yield is 53.7%.

[0136] MALDI-TOF: m / z: calculated for C 54 H 30 N4: 734.25, found: 6734.16. Elemental analysis results of the compound: C, 88.26; H, 4.09; N, 7.61.

[0137] Example 7: Synthesis of U-49

[0138] The present example provides a method for synthesizing an organic compound, comprising the following steps:

[0139]

[0140] (1) Synthesis of U-49-1: Under a nitrogen environment, raw material A 10 (25 g), raw material B 49 (37.3 g), tetrakis(triphenylphosphine)palladium (0.8 g), and X-phos (0.8 g) were sequentially added to a 1000 mL three-necked flask, then 500 mL of dry toluene was injected into the flask and vacuumed, replaced with nitrogen three times, heated to 110°C to reflux for 10 hours, after the reaction was completed, the reaction mixture was poured into 500 mL of deionized water and stirred rapidly, during which the product was continuously precipitated, after vacuum filtration, the product was dissolved again with dichloromethane and extracted with saturated brine three times, the organic phase was combined and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:15) to obtain 32.2 g of intermediate U-49-1, with a yield of 78.2%.

[0141] (2) Synthesis of U-49-2: Under a nitrogen environment, intermediate U-49-1 (25 g) and sodium tert-butoxide (44 g) were sequentially added to a 500 mL three-necked flask, then 220 mL of dry toluene was injected into the flask and vacuumed, replaced with nitrogen three times, heated to 110°C to reflux for 10 hours, after the reaction was completed, the reaction mixture was poured into 500 mL of deionized water and stirred rapidly, during which the product was continuously precipitated, after vacuum filtration, the product was dissolved again with dichloromethane and extracted with saturated brine three times, the organic phase was combined and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:10) to obtain 14.6 g of intermediate U-49-2, with a yield of 61.5%.

[0142] (3) Synthesis of U-49-3: Compound U-49-2 (11 g), bis-tricyclohexylphosphine palladium dichloride (0.6 g) and cesium carbonate (22 g) were sequentially added to a 500 mL three-necked flask under nitrogen atmosphere, and then 200 mL of dry dimethylacetamide and 12 mL of tert- butyric acid were injected into the flask and vacuum-nitrogen substitution was performed three times, and the reaction was heated to 170°C to reflux for 8 h. After the reaction was completed, the reaction mixture was poured into 500 mL of deionized water and stirred rapidly, and the product was precipitated during the stirring. The filter cake was dissolved in dichloromethane and extracted with saturated brine three times, and the organic phase was separated and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:8) to obtain 5.3 g of compound U-49-3, with a yield of 53.2%.

[0143] (4) Synthesis of U-49: Intermediate U-49-3 (9 g), raw material C 10 (10 g), palladium trifluoroacetate (0.35 g) and cesium carbonate (12 g) were sequentially added to a 500 mL three-necked flask under nitrogen atmosphere, and then 200 mL of dry toluene was injected into the flask and vacuum-nitrogen substitution was performed three times, and the reaction was heated to 110°C to reflux for 10 h. After the reaction was completed, the reaction mixture was poured into 500 mL of deionized water and stirred rapidly, and the product was precipitated during the stirring. The filter cake was dissolved in dichloromethane and extracted with saturated brine three times, and the organic phase was separated and purified by silica gel column chromatography (eluent dichloromethane: petroleum ether = 1:8) to obtain 8.1 g of a solid powder, which was compound U-49, with a yield of 48.6%.

[0144] MALDI-TOF: m / z: calculated: 662.22, found: 622.12. Compound elemental analysis results: C, 83.16; H, 3.95; N, 12.54.

[0145] Comparative Example 1:

[0146] The present comparative example provides a method for synthesizing an organic compound, comprising the following steps:

[0147]

[0148] (1) Synthesis of N1-1: Compound A n (20.2 g, 50 mmol), compound A B(17.2g, 100mmol), tetrakis(triphenylphosphine)palladium (3.5g, 3mmol), tetrabutylammonium bromide (8.1g, 25mmol) and sodium hydroxide (4g, 100mmol) were added into a 500mL three-necked flask in turn, then 200mL of toluene and 50mL of deionized water were added, vacuumed, replaced with nitrogen for three times, and then heated to 110°C for stirring for 24h. After the reaction was completed, most of the solvent was removed by rotary evaporation, the reaction solution was dissolved in dichloromethane, washed with water for three times, and then the combined organic phase was separated and purified by silica gel column chromatography (eluent: petroleum ether) to obtain 18.7g of compound N1-1, with a yield of 75%.

[0149] (2) Synthesis of N1-2: Compound N1-1 (14.9g, 30mmol) and 100mL of N,N-dimethylformamide were added into a 250mL single-necked flask, and 30mmol of NBS in N,N-dimethylformamide was added dropwise under ice bath, and then the reaction was stirred in dark for 12h. After the reaction was completed, the reaction solution was poured into 300mL of water, and then filtered. The filter residue was recrystallized to obtain 17.3g of compound N1-2, with a yield of 90%.

[0150] (3) Synthesis of N1: Compound N1-2 (34.4g, 20mmol), compound 4-5 (11.5g, 20mmol), tetrakis(triphenylphosphine)palladium (0.7g, 0.6mmol), tetrabutylammonium bromide (3.2g, 10mmol) and sodium hydroxide (1.6g, 40mmol) were added into a 500mL three-necked flask in turn, then 200mL of toluene and 50mL of deionized water were added into the flask and vacuumed, replaced with nitrogen for three times, heated to 110°C for refluxing for 12h, and then the reaction was completed. After the reaction was completed, the solvent was removed by rotary evaporation, and then the product was dissolved in dichloromethane and extracted with saturated brine for three times. The combined organic phase was separated and purified by silica gel column chromatography (eluent: dichloromethane: petroleum ether = 1:10) to obtain 18.7g of comparative compound N1 (solid powder), with a yield of 85%.

[0151] Application Example 1

[0152] This application example provides an OLED device 10, which has a structure as shown in Figure 1 The OLED device 10 includes a glass substrate 11, an ITO anode 12, a hole injection layer 13, a first hole transport layer 14, a second hole transport layer 15, a light-emitting layer 16, an electron transport layer 17, and a cathode 18, which are sequentially stacked.

[0153] The preparation method of the OLED device is as follows:

[0154] 1) Glass substrate 11 was cut into 50 mm x 50 mm x 0.7 mm, and cleaned by ultrasonic treatment in isopropanol and deionized water for 30 min, respectively, and then exposed to ozone for about 10 min; the obtained glass substrate with ITO anode 12 was installed on a vacuum deposition device;

[0155] 2) On ITO anode 2, compound HI was vacuum evaporated as a hole injection layer 13, with a thickness of 30 nm;

[0156] 3) On hole injection layer 13, compound HT-1 was vacuum evaporated as a first hole transport layer 14, with a thickness of 60 nm;

[0157] 4) On first hole transport layer 14, compound HT-2 was vacuum evaporated as a second hole transport layer 15, with a thickness of 10 nm;

[0158] 5) On second hole transport layer 15, compound U-10 (provided in Example 1) and red guest material RD were vacuum evaporated as a light-emitting layer 16, with a thickness of 40 nm, in a weight ratio of 100:3;

[0159] 6) On light-emitting layer 160, compound ET and Liq were vacuum evaporated as an electron transport layer 17, with a thickness of 30 nm, in a weight ratio of 50:50;

[0160] 7) On electron transport layer 17, an aluminum electrode was vacuum evaporated as a cathode 18, with a thickness of 100 nm.

[0161] The structures of the materials HI, HT-1, HT-2, red guest material RD, ET and Liq mentioned in the above steps are as follows:

[0162]

[0163]

[0164] Application Example 2

[0165] This application example provides an OLED device, which differs from that of Application Example 1 only in that the organic compound U-10 in step (5) is replaced with an equal amount of the organic compound U-36 provided in Example 2 of the present application; the other preparation steps are the same.

[0166] Application Example 3

[0167] This application example provides an OLED device, which differs from that of Application Example 1 only in that the organic compound U-10 in step (5) is replaced with an equal amount of the organic compound U-40 provided in Example 3 of the present application; the other preparation steps are the same.

[0168] Application Example 4

[0169] The application example provides an OLED device, which is different from the application example 1 only in that the organic compound U-10 in step (5) is replaced by an equal amount of the organic compound U-45 provided in the application example 4; and other preparation steps are the same.

[0170] Application Example 5

[0171] The application example provides an OLED device, which is different from the application example 1 only in that the organic compound U-10 in step (5) is replaced by an equal amount of the organic compound U-46 provided in the application example 5; and other preparation steps are the same.

[0172] Application Example 6

[0173] The application example provides an OLED device, which is different from the application example 1 only in that the organic compound U-10 in step (5) is replaced by an equal amount of the organic compound U-48 provided in the application example 6; and other preparation steps are the same.

[0174] Application Example 7

[0175] The application example provides an OLED device, which is different from the application example 1 only in that the organic compound U-10 in step (5) is replaced by an equal amount of the organic compound U-49 provided in the application example 6; and other preparation steps are the same.

[0176] Application Comparative Example 1

[0177] The comparative example is different from the application example 1 only in that the organic compound U-10 in step (5) is replaced by an equal amount of N1 provided in the application comparative example 1; and other preparation steps are the same.

[0178] Performance evaluation of the OLED device:

[0179] Test method: lifetime test method, initially at a constant current density corresponding to 1000 nits, the continuous working time of the device when the luminous intensity of the device decreases to 95% of the initial value.

[0180] Current efficiency test method, using an I-V-L test device, the current density corresponding to a luminance of 1000 nits is measured, and the current efficiency is calculated.

[0181] The test results are shown in Table 1.

[0182] Table 1

[0183]

[0184] As can be seen from the data in Table 1, compared with the device in Comparative Example 1, the organic compound provided in this application enables the OLED device to have higher current efficiency and longer lifespan.

[0185] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of this application, and not to limit them. Although this application has been described in detail with reference to the foregoing embodiments, those skilled in the art should understand that modifications can still be made to the technical solutions described in the foregoing embodiments, or equivalent substitutions can be made to some or all of the technical features therein. These modifications or substitutions do not cause the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of this application, and they should all be covered within the scope of the claims and specification of this application. In particular, as long as there is no structural conflict, the various technical features mentioned in the embodiments can be combined in any way. This application is not limited to the specific embodiments disclosed herein, but includes all technical solutions falling within the scope of the claims.

Claims

1. An organic compound, characterized in that, Specifically, the structure is shown in Equation I below: In this context, A, B, and C are independently selected from phenyl or naphthyl; D is independently selected from phenyl, naphthyl, or pyridyl; A is bonded to B to form a ring; The L is selected from any one of phenylene, biphenylene, naphthylene, or C3-C12 nitrogen-containing heteroaryl groups; The E is selected from any one of the structural formulas shown below, from t-6 to t-28: In this context, dashed lines represent the bonding sites of functional groups.

2. An organic compound, characterized in that, The organic compound is selected from any one of the compounds shown below, from U-9 to U-54:

3. 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, wherein the material of the organic thin film layer includes an organic compound as described in any one of claims 1-2.

4. A display panel, characterized in that, The display panel includes the OLED device as described in claim 3.

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