Organic compound, organic light-emitting device and display panel

Abstract

The invention relates to an organic compound, an organic light-emitting device and a display panel. The organic compound has a structural formula as shown in a formula (1): # imgabs0 #. The organic compound provided by the invention contains tetrahydrocyclobutane dipyrroletetraone, so that the organic compound has an excellent tetrahydrocyclobutane dipyrroletetraone structure with a non-conjugated plane connection design; the organic compound provided by the invention has a relatively high first singlet excited state energy level and a relatively high glass transition temperature; the reasonable introduction of the trifluoromethyl group can make the material have a low refractive index; in addition, when a film layer formed by the organic compound is combined with a high-refractive-index film layer to form a covering layer and the covering layer is applied to the organic light-emitting device, the light-emitting efficiency and the color purity of the device can be remarkably improved, and the problem of visual deviation can be solved.

Description

Technical Field

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

[0002] Organic Light-Emitting Diodes (OLEDs) have been widely used in applications such as main display screens due to their excellent display performance and have made remarkable progress in the process of practical application. Although the research and development of organic electroluminescence technology have developed rapidly, there are still many challenges, especially the need to improve the External Quantum Efficiency (EQE). For organic light-emitting devices, the luminescent quantum efficiency is not only a comprehensive reflection of the device performance but also an important standard for measuring the device quality.

[0003] Currently, some excellent organic light-emitting materials have been applied in the commercial field. By using specific arylamine derivatives with high refractive indices or materials meeting specific parameter requirements as the covering layer, the light extraction efficiency and color purity can be optimized. However, it is difficult to increase the refractive index of the organic compound in the covering layer. Therefore, in order to further improve the luminescence efficiency of organic light-emitting elements without adding too many materials, researchers have explored a double-covering-layer structure composed of a low-refractive-index covering layer and a high-refractive-index covering layer. For example, although Samsung's US20210159427A1 patent uses a combination of a low-refractive-index material and a high-refractive-index material to form a double-layer covering layer, its low-refractive-index material is a coordination compound with poor coordination bond stability. This patent only records that it can improve the device luminescence efficiency and does not record the impact on device viewing angle deviation. Although Hodogaya's WO2022075396A1 patent also uses a similar double-layer covering layer structure, its low-refractive-index material has a structure with adamantane as the core and aryl or heteroaryl groups connected by bridging groups. The disclosed structure has a low molecular weight and a low evaporation temperature, less than 200 °C. During the evaporation process, the evaporation rate is unstable, prone to spraying, polluting the evaporation equipment, and prone to crystallization after coating, affecting the device stability, especially the high-temperature device stability. And this patent also only records that it can improve the device luminescence efficiency and does not record the impact on device viewing angle deviation.

[0004] In order to continuously improve the performance of OLED devices, not only innovation in the OLED device structure and manufacturing process is required, but also continuous research and innovation in OLED optoelectronic functional materials to create higher-performance OLED functional materials. Therefore, it is a long-term need in this field to find suitable low-refractive-index materials to match high-refractive-index materials as a double-layer covering layer for OLED devices to solve the above problems. Summary of the Invention

[0005] Embodiments of the present application provide an organic compound, an organic light-emitting device, and a display panel. The organic compound has a low refractive index and can be used as a covering layer of the organic light-emitting device to improve the light extraction efficiency and improve the angle dependence of the display panel.

[0006] Embodiments of the present application provide an organic compound having a structural formula shown in Formula (1):

[0007]

[0008] Wherein, R1 to R 10 are the same or different and each independently selected from hydrogen, deuterium, halogen, nitro, cyano, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted fluoroalkyl having 1 to 10 carbon atoms, substituted or unsubstituted fluorocycloalkyl having 1 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted arylamino having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylamino having 3 to 20 carbon atoms containing at least one heteroatom, and the heteroatom in the heteroaryl or the heteroarylamino is selected from at least one of nitrogen atom, oxygen atom, phosphorus atom, sulfur atom or silicon atom;

[0009] R1 to R 10 contains at least one trifluoromethyl group.

[0010] According to the above object of the present application, embodiments of the present application further provide an organic light-emitting device, which includes:

[0011] A first electrode;

[0012] An organic functional layer disposed on one side of the first electrode;

[0013] A second electrode disposed on the side of the organic functional layer away from the first electrode;

[0014] A covering layer disposed on the side of the second electrode away from the first electrode;

[0015] Wherein, the material of the covering layer includes at least one of the organic compounds.

[0016] According to the above object of the present application, embodiments of the present application further provide a display panel, which includes the organic light-emitting device.

[0017] The present application provides an organic compound, an organic light-emitting device, and a display panel. The organic compound contains tetrahydrocyclobutane dipyrrole tetrone. Therefore, the organic compound has an excellent tetrahydrocyclobutane dipyrrole tetrone structure with a "non-conjugated planar connection design", enabling the organic compound provided by the present application to have a relatively high first singlet excited state energy level and a relatively high glass transition temperature. The reasonable introduction of trifluoromethyl groups can endow it with a relatively low refractive index. In addition, when a film layer formed by using this organic compound combines with a high refractive index film layer to form a cover layer and is applied to an organic light-emitting device, it can significantly improve the light-emitting efficiency and color purity of the device and can be used to improve the problem of visual deviation.

[0018] Other features and advantages of the present application will be described in detail in the subsequent specific implementation section. Brief Description of the Drawings

[0019] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following will briefly introduce the drawings required for the description of the embodiments. Obviously, the drawings in the following description are only some embodiments of the present application. For those skilled in the art, without creative efforts, other drawings can be obtained based on these drawings.

[0020] In order to more comprehensively understand the present application and its beneficial effects, the following will be described in conjunction with the drawings, where the same reference numerals represent the same parts in the following description.

[0021] Figure 1 It is the first structural schematic diagram of the organic light-emitting device provided by the embodiment of the present application;

[0022] Figure 2 It is the second structural schematic diagram of the organic light-emitting device provided by the embodiment of the present application;

[0023] Figure 3 It is the third structural schematic diagram of the organic light-emitting device provided by the embodiment of the present application.

[0024] Description of the Reference Numerals:

[0025] 10. Substrate; 11. First electrode; 12. Second electrode; 20. Organic functional layer; 21. Hole injection layer; 22. Hole transport layer; 23. Electron blocking layer; 24. Light-emitting layer; 25. Hole blocking layer; 26. Electron transport layer; 27. Electron injection layer; 30. Cover layer; 31. First sub-layer; 32. Second sub-layer. Specific Embodiments

[0026] Throughout this specification, unless the contrary is expressly stated, "comprising" any component will be understood to imply the inclusion of other elements, rather than the exclusion of any other elements. Further, it should be understood that throughout this specification, when an element such as a layer, film, region or substrate is referred to as being "on" or "above" another element, it can be "directly on" the other element, or intervening elements may also be present. Additionally, "on" or "above" means located above the target portion, and does not necessarily mean above in the direction of gravity.

[0027] As used herein, "n@460nm" refers to the refractive index of the material relative to vacuum for blue light with a wavelength of 460nm; "n@525nm" refers to the refractive index of the material relative to vacuum for green light with a wavelength of 525nm; "n@620nm" refers to the refractive index of the material relative to vacuum for red light with a wavelength of 620nm; "k@380nm" refers to the extinction coefficient of the material relative to vacuum for a wavelength of 380nm.

[0028] As used herein, an aryl group having 6 to 20 carbon atoms refers to a monovalent group including a carbocyclic aromatic system having 6 to 20 carbon atoms as ring-forming atoms. Non-limiting examples of aryl groups having 6 to 20 carbon atoms may include phenyl, biphenyl, phenanthryl, terphenyl, naphthyl, phenanthryl, benzophenanthryl, etc., but are not limited thereto. When an aryl group having 6 to 20 carbon atoms includes two or more rings, these rings may be fused to each other.

[0029] As used herein, a heteroaryl group having 2 to 20 carbon atoms refers to a monovalent group including a carbocyclic aromatic system having at least one heteroatom selected from a nitrogen atom, an oxygen atom, a phosphorus atom, a sulfur atom, or a silicon atom as a ring-forming atom and 2 to 20 carbon atoms. Non-limiting examples of heteroaryl groups having 2 to 20 carbon atoms may include furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, benzofuryl, benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl, indazolyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, 2,1,3-benzoxadiazole, quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, naphthyridinyl, benzotriazinyl, benzoxazinyl, purinyl, pteridinyl, indolizinyl, benzothiazinyl, acridinyl, phenazinyl, phenothiazinyl, phenoxazinyl, dibenzofuryl, dibenzothienyl, carbazolyl, naphthofuryl, quinolinyl, isoquinolinyl, indolo[1,2-f]phenanthridinyl, imidazo[2,1-a]isoquinolinyl, imidazo[1,2-a]quinolinyl, benzo[4,5]imidazo[1,2-a]pyridinyl, imidazo[1,2-a]pyridinyl, benzofuro[3,2-c]quinolinyl, naphtho[1,2-b]benzofuryl, naphtho[2,3-b]benzofuryl, etc., and also include aromatic combined groups with heteroatoms, but are not limited thereto.

[0030] The alkyl group having 1 to 10 carbon atoms (including straight-chain alkyl groups and branched-chain alkyl groups) described in the present invention refers to methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, hexyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, etc., but is not limited thereto.

[0031] The halogen atom described in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0032] In the text, the term "amino group" refers to a primary amino group, a secondary amino group, or a tertiary amino group having a specified number of carbon atoms in each case (for example, 1 to 100, preferably 1 to 50, preferably 1 to 30, preferably 1 to 20, still preferably 1 to 12, more preferably 1 to 6).

[0033] As used herein, the term "aryl amino" refers to a primary, secondary, or tertiary amino group substituted with an aryl group. The term "heteroaryl amino" refers to a primary, secondary, or tertiary amino group substituted with a heteroaryl group.

[0034] "Arylene amino" refers to a divalent group of an aryl amino system, and "heteroarylene amino" refers to a divalent group of a heteroaryl amino system.

[0035] "Substituted or unsubstituted", "substituted" means that a hydrogen atom in the structure can be further substituted by other groups.

[0036] An embodiment of the present application provides an organic compound having a structural formula shown in Formula (1):

[0037]

[0038] Wherein, R1 to R 10 are the same or different and each independently selected from hydrogen, deuterium, halogen, nitro, cyano, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted fluoroalkyl having 1 to 10 carbon atoms, substituted or unsubstituted fluorocycloalkyl having 1 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted aryl amino having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl amino having 3 to 20 carbon atoms containing at least one heteroatom, and the heteroatom in the heteroaryl or the heteroaryl amino is selected from at least one of a nitrogen atom, an oxygen atom, a phosphorus atom, a sulfur atom, or a silicon atom;

[0039] R1 to R 10 contains at least one trifluoromethyl group.

[0040] In the process of implementation and application, the organic compound provided by the embodiment of the present application contains tetrahydrocyclobutane dipyrrole tetrone. Therefore, the organic compound has an excellent tetrahydrocyclobutane dipyrrole tetrone structure of "non-conjugated planar connection design", making the organic compound provided by the present application have a relatively high first singlet excited state energy level and a relatively high glass transition temperature. The reasonable introduction of the trifluoromethyl group can give it a relatively low refractive index. In addition, when a film layer formed by using the organic compound is combined with a high refractive index film layer to form a covering layer and applied to the organic light-emitting device 100, the luminous efficiency and color purity of the device can be significantly improved, and it can be used to improve the viewing angle deviation problem.

[0041] It should be noted that the introduction of the trifluoromethyl group can reduce the refractive index of the organic compound, and further make the covering layer made of the organic compound have a lower refractive index.

[0042] Specifically, in some embodiments, R1 to R 10 are the same or different and each independently selected from hydrogen, deuterium, halogen, nitro, cyano, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, fluoromethyl, fluoromethoxy, fluorine-substituted cyclohexyl, methyl, tert-butyl, cyclohexyl, adamantane, any one of the following groups which are substituted or unsubstituted:

[0043]

[0044]

[0045] wherein, n1 is selected from 1, 2, 3, 4 or 5; the expression of "-" crossing the ring structure indicates the bonding site at any bondable position on the ring structure; "*" represents the bonding site.

[0046] It should be noted that in the above-listed group structures of R1 to R 10 , the substituted or unsubstituted substituents are each independently selected from one or more of hydrogen, protium, deuterium, tritium, halogen, cyano, nitro, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, fluoromethyl, fluoromethoxy, fluorine-substituted cyclohexyl, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, cyclohexyl, adamantyl, phenyl, biphenyl, trifluoromethyl-substituted phenyl, trifluoromethyl-substituted biphenyl, fluorine-substituted phenyl, fluorine-substituted biphenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, fluorenyl, carbazolyl, but are not limited to the above structures.

[0047] It can be understood that at least one of R1 to R 10 contains trifluoromethyl; it can be regarded as at least one of R1 to R 10 being trifluoromethyl, or at least one of R1 to R 10 containing trifluoromethyl.

[0048] In some embodiments, R1 to R 10 are the same or different and each independently selected from hydrogen, fluorine, nitro, cyano, methyl, trifluoromethyl, phenyl substituted with at least one trifluoromethyl, phenyl substituted with at least one fluorine, cyclohexyl, cyclohexyl substituted with at least one fluorine, dibenzofuranyl, diphenylamine.

[0049] In some embodiments, the organic compound is selected from one of the following compounds:

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058]

[0059]

[0060] In addition, please refer to Figure 1 , this embodiment of the present application further provides an organic light-emitting device 100, and the organic light-emitting device 100 includes a first electrode 11, an organic functional layer 20, a second electrode 12, and a covering layer 30.

[0061] Wherein, the organic functional layer 20 is disposed on one side of the first electrode 11; the second electrode 12 is disposed on the side of the organic functional layer 20 away from the first electrode 11; the covering layer 30 is disposed on the side of the second electrode 12 away from the first electrode 11;

[0062] Furthermore, the material of the covering layer 30 includes at least one of the organic compounds as described in the above embodiments.

[0063] In some embodiments, please refer to Figure 2 , the organic light-emitting device 100 further includes a substrate 10, and the first electrode 11 is disposed on the substrate 10, and the first electrode 11 is located between the substrate 10 and the organic functional layer 20.

[0064] In some embodiments, the organic functional layer 20 includes a hole injection layer 21 disposed between the first electrode 11 and the second electrode 12, a hole transport layer 22 disposed between the hole injection layer 21 and the second electrode 12, an electron blocking layer 23 disposed between the hole transport layer 22 and the second electrode 12, a light-emitting layer 24 disposed between the electron blocking layer 23 and the second electrode 12, a hole blocking layer 25 disposed between the light-emitting layer 24 and the second electrode 12, an electron transport layer 26 disposed between the hole blocking layer 25 and the second electrode 12, and an electron injection layer 27 disposed between the electron transport layer 26 and the second electrode 12.

[0065] It is understandable that in other embodiments of the present application, the organic functional layer 20 includes the light-emitting layer 24. In addition, the organic functional layer 20 may further include at least one of the hole injection layer 21, the hole transport layer 22, the electron blocking layer 23, the hole blocking layer 25, the electron transport layer 26, and the electron injection layer 27.

[0066] In some embodiments, the substrate 10 can be selected from any substrate used in typical organic light-emitting devices. It can be a glass or transparent plastic substrate, or a substrate of an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strengths, thermal stabilities, transparencies, surface smoothness, and water resistances, and are used in different directions according to the properties of the substrates.

[0067] In some embodiments, the first electrode 11 can be an anode or a cathode. Here, the first electrode 11 can be merely a reflective electrode such as a reflective film formed of silver (Ag), magnesium (Mg), aluminum (Al), gold (Au), nickel (Ni), chromium (Cr)), or an alloy thereof, or an electrode formed by combining a reflective film and a transparent or semi-transparent electrode, for example, a transparent or semi-transparent electrode layer having a high work function and formed on the reflective film. The transparent or semi-transparent electrode layer can be formed of indium tin oxide (ITO), indium zinc oxide (IZO), zinc oxide (ZnO), aluminum zinc oxide (AZO), indium gallium oxide (IGO), indium oxide (In2O3), or tin oxide (SnO2); it can also be formed by combining a metal and an oxide, for example, formed of ITO / Ag / ITO, IGO / Al / IGO, or AZO / Ag / AZO.

[0068] In some embodiments, the first electrode 11 can be formed by methods such as sputtering, ion plating, vacuum evaporation, spin coating, electron beam evaporation, or chemical vapor deposition (CVD), and is preferably formed by sputtering.

[0069] In some embodiments, the thickness of the first electrode layer 11 can be 5 nm - 1 μm, preferably 10 nm - 1 μm, more preferably 10 nm - 500 nm, particularly preferably 10 nm - 300 nm, and most preferably 10 nm - 200 nm.

[0070] In some embodiments, the thickness range of the organic functional layer 20 is 50 nm - 1000 nm.

[0071] In some embodiments, the materials of the hole injection layer 21, the hole transport layer 22, and the electron blocking layer 23 can be selected from any of the known related materials for OLED devices for use. And at least one of the hole injection layer 21 and the hole transport layer 22 may further include a charge generation material for improving conductivity.

[0072] The charge generation material may be a p-dopant. Non-limiting compounds of p-dopants are, for example, quinone derivatives such as tetracyanoquinodimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ); or hexaazatriphenylene derivatives such as 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene (HAT-CN); or cyclopropane derivatives such as 4,4',4”-((1E,1'E,1”E)-cyclopropane-1,2,3-triylidene tris(cyanomethanylylidene)) tris(2,3,5,6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but not limited thereto.

[0073] The triplet (T1) energy level of the material of the electron blocking layer 23 is higher than the T1 energy level of the host material in the light-emitting layer 24, which can play a role in blocking the energy loss of the material of the light-emitting layer 24; the HOMO energy level of the material of the electron blocking layer 23 is between the HOMO energy level of the material of the hole transport layer 22 and the HOMO energy level of the host material of the light-emitting layer 24, which is beneficial to the injection of holes from the first electrode 11 into the light-emitting layer 24. At the same time, it is required that the material of the electron blocking layer 23 has a high hole mobility, which is beneficial to hole transport and reduces the device application power; the LUMO energy level of the material of the electron blocking layer 23 is higher than the LUMO energy level of the host material of the light-emitting layer 24, which plays a role in blocking electrons, that is, it is required that the material of the electron blocking layer 23 has a wide bandgap (Eg). The material of the electron blocking layer 23 that meets the above conditions may include triarylamine derivatives, fluorene derivatives, spirofluorene derivatives, dibenzofuran derivatives, carbazole derivatives, etc. Among them, triarylamine derivatives are preferred, such as N4,N4-bis([1,1'-biphenyl]-4-yl)-N4'-phenyl N4'-[1,1'4',1”-terphenyl]-4-yl-[1,1'-biphenyl]-4,4'-diamine; spirofluorene derivatives such as N-([1,1'-diphenyl]-4-yl)-N-(9,9-dimethyl-9H-fluoren-2-yl)-9,9'-spirobifluorene-2-amine; dibenzofuran derivatives such as N,N-bis([1,1'-biphenyl]-4-yl)-3'-(dibenz[b,d]furan-4-yl)-[1,1'-biphenyl]-4-amine, but not limited thereto.

[0074] In order to obtain a high-efficiency OLED device, the light-emitting layer 24 can use the same kind of doping material or multiple doping materials. The doping material can be a pure fluorescent material, a thermally activated delayed fluorescence (TADF) material, or a phosphorescent material, or a combination of different fluorescent materials, TADF materials, and phosphorescent materials. The light-emitting layer 24 can be a single light-emitting layer material or a composite light-emitting layer material stacked horizontally or vertically. The light-emitting layer 24 constituting the above OLED light-emitting body can be selected from the following various structures:

[0075] (1) A single organic light-emitting layer material;

[0076] (2) Any combination of a blue organic light-emitting layer material and any one of a green, yellow, or red light-emitting layer material, without considering the order;

[0077] (3) Any combination of two of a blue organic light-emitting layer material and a green, yellow, or red light-emitting layer material, without considering the order;

[0078] (4) A blue organic light-emitting layer material, a green organic light-emitting layer material, and a red organic light-emitting layer material arranged horizontally.

[0079] In order to regulate the effective combination of carrier charges in the light-emitting layer 24, the film thickness of the light-emitting layer 24 constituting the above OLED light-emitting body can be adjusted arbitrarily as needed, or light-emitting layers of different colors can be alternately stacked and combined as needed. Different functional charge blocking layers can also be added to the film layer adjacent to the light-emitting layer 24.

[0080] The host material of the light-emitting layer 24 in the organic light-emitting device 100 not only needs to have bipolar charge transport characteristics but also needs to have an appropriate energy level to effectively transfer the excitation energy generated by the recombination of electrons and holes to the guest light-emitting material, that is, the doping material. Such materials can include stilbene arylidene derivatives, stilbene derivatives, carbazole derivatives, triarylamine derivatives, anthracene derivatives, pyrene derivatives, triazine derivatives, xanthenone derivatives, triphenylene derivatives, triazine derivatives, hexabenzocoronene derivatives, or bis(2-methyl-8-quinolinolato)(p-phenylphenolato)aluminum (BAlq), etc.

[0081] In some embodiments, the materials of the hole blocking layer 25 and the electron transport layer 26 can be selected from any materials with electron transport properties for use in OLEDs. Such materials can include 1,3-bis[5'-(p-tert-butylphenyl)-1,3,4-oxadiazol-2'-yl]benzene, oxadiazole derivatives such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole, triazole derivatives such as 3-(4'-tert-butylphenyl)-4-phenyl-5-(4''-biphenyl)-1,2,4-triazole, triazine derivatives, quinoline derivatives, quinoxaline derivatives, diphenylquinone derivatives, nitro-substituted fluorenone derivatives, thiopyran dioxide derivatives, anthraquinone dimethane derivatives, thiopyran dioxide derivatives, heterocyclic tetracarboxylic anhydrides such as naphthylperylene, carbodiimide, fluorene derivatives, anthraquinone dimethane derivatives, anthrone derivatives, stilbenylpyrazine derivatives, silole derivatives, phenanthroline derivatives, or imidazopyridine derivatives, etc.

[0082] In some embodiments, the organic functional layer 20 can be composed of small molecule organic materials or polymer materials, and the organic functional layer 20 can be prepared by a variety of methods, such as vacuum evaporation, solution spin coating, screen printing, inkjet printing, etc.

[0083] In some embodiments, the second electrode 12 can be a cathode or an anode, and can be a transparent electrode or a semi-transparent electrode. The second electrode 12 can be made of a thin film with a low work function formed by lithium, calcium, lithium fluoride / calcium, lithium fluoride / aluminum, aluminum, silver, magnesium, or an alloy thereof. Further, the second electrode 12 can be made of an alloy including silver and at least one metal, and the at least one metal includes aluminum, platinum, ytterbium, chromium, or magnesium. And, the weight ratio of Ag in the alloy can be the same as, greater than, or less than the weight ratio of other metals. For example: the second electrode 12 can be formed of an Ag-Mg alloy, where the mass ratio of Ag and Mg can be from 90:10 to 10:90. Or, the second electrode 12 can be formed of an alloy including at least one metal such as silver, gold, platinum, copper, nickel, or tungsten and at least one metal such as ytterbium, indium, magnesium, or chromium. These metal films can form transparent or semi-transparent electrodes by adjusting the thickness of the film. Therefore, the light generated by the organic functional layer 20 can be emitted through the second electrode 12. And, the thickness of the second electrode 12 can be 5 - 20 nm.

[0084] In some embodiments, the second electrode 12 can be prepared by, for example, vacuum evaporation.

[0085] It should be noted that the first electrode 11 can be one of an anode or a cathode, and the second electrode 12 can be the other of the anode or the cathode. In the embodiments of the present application, the first electrode 11 can be taken as an example of an anode, and the second electrode 12 can be taken as an example of a cathode for description.

[0086] In the embodiments of the present application, the covering layer 30 is disposed on a side of the second electrode 12 away from the organic functional layer 20, and the covering layer 30 includes at least one of the organic compounds as described in the above embodiments.

[0087] In some embodiments, please refer to Figure 3 , the covering layer 30 includes a first sub-layer 31 and a second sub-layer 32 which are stacked, and the first sub-layer 31 is disposed between the second sub-layer 32 and the second electrode 12.

[0088] Among them, the material of the first sub-layer 31 includes at least one of the organic compounds as described in the above embodiments.

[0089] In some embodiments, the refractive index of the material of the first sub-layer 31 is less than the refractive index of the material of the second sub-layer 32. The refractive index of the material of the first sub-layer 31 for light with a wavelength of 460 nm is less than or equal to 1.65, the refractive index of the material of the second sub-layer 32 for light with a wavelength of 460 nm is greater than or equal to 1.85, and the difference between the refractive index of the material of the second sub-layer 32 for light with a wavelength of 460 nm and the refractive index of the material of the first sub-layer 31 for light with a wavelength of 460 nm is greater than or equal to 0.3.

[0090] Furthermore, the band gap E of the material of the first sub-layer 31 g is greater than 3.0 eV, preferably greater than 3.5 eV;

[0091] More preferably, the difference between the refractive index of the material of the first sub-layer 31 for light with a wavelength of 460 nm and the refractive index of the material of the first sub-layer 31 for light with a wavelength of 620 nm is less than or equal to 0.3.

[0092] In some embodiments, the total film thickness range of the covering layer 30 is 15 nm - 300 nm, more preferably 30 nm - 200 nm, still more preferably 40 nm - 100 nm, and most preferably 50 nm - 80 nm; the film thickness of the first sub-layer 31 is 1 nm - 150 nm, preferably 5 nm - 100 nm, more preferably 10 nm - 50 nm; the film thickness of the second sub-layer 32 is 1 nm - 150 nm, preferably 10 nm - 100 nm, more preferably 20 nm - 80 nm.

[0093] In some embodiments, the refractive index of the first sub-layer 31 is less than that of the second sub-layer 32; the refractive index of the first sub-layer 31 for blue light with a wavelength of 460 nm is less than or equal to 1.65, preferably less than or equal to 1.60, preferably less than or equal to 1.55; preferably less than or equal to 1.50; the refractive index of the first sub-layer 31 for blue light with a wavelength of 525 nm is less than or equal to 1.65, preferably less than or equal to 1.60, preferably less than or equal to 1.55; preferably less than or equal to 1.50; the refractive index of the first sub-layer 31 for blue light with a wavelength of 620 nm is less than or equal to 1.65, preferably less than or equal to 1.60, preferably less than or equal to 1.55; preferably less than or equal to 1.50; the refractive index of the second sub-layer 32 for blue light with a wavelength of 460 nm is greater than or equal to 1.85, preferably greater than or equal to 1.9, preferably greater than or equal to 2.0, preferably greater than or equal to 2.1, preferably greater than or equal to 2.2; more preferably greater than or equal to 2.3; the refractive index of the second sub-layer 32 for blue light with a wavelength of 525 nm is greater than or equal to 1.85, preferably greater than or equal to 1.9, preferably greater than or equal to 2.0, preferably greater than or equal to 2.1, more preferably greater than or equal to 2.2; the refractive index of the second sub-layer 32 for blue light with a wavelength of 620 nm is greater than or equal to 1.8, preferably greater than or equal to 1.9, preferably greater than or equal to 2.0, more preferably greater than or equal to 2.1.

[0094] In some embodiments, the difference between the refractive index of the first sub-layer 31 for light with a wavelength of 460 nm and the refractive index of the second sub-layer 32 for light with a wavelength of 460 nm is greater than or equal to 0.3; preferably greater than or equal to 0.4; preferably greater than or equal to 0.5; preferably greater than or equal to 0.6; preferably greater than or equal to 0.7; more preferably greater than or equal to 0.8.

[0095] In some embodiments, the material of the second sub-layer 32 includes the following structures (see Patent WO2020027389A1, CN115611884B, and WO2015001726A1 respectively), but is not limited to the following structures:

[0096]

[0097] In some embodiments, the total film thickness of the cover layer 30 can be 15 nm - 300 nm, preferably 30 nm - 200 nm, preferably 40 nm - 100 nm, and most preferably 50 nm - 80 nm.

[0098] The film thickness of the first sub-layer 31 can be 1 nm - 150 nm, preferably 5 nm - 100 nm, and more preferably 10 nm - 50 nm.

[0099] The film thickness of the second sub-layer 32 is 1 nm - 150 nm, preferably 10 nm - 100 nm, and more preferably 20 nm - 80 nm.

[0100] In some embodiments, the film thickness of the second sub-layer 32 may be the same as or different from that of the first sub-layer 31; and the film thickness of the second sub-layer 32 may be greater than or equal to that of the first sub-layer 31.

[0101] In some embodiments, the cover layer 30 may be composed of the organic compound based on the heteroarylamine structure, and the cover layer 30 can be prepared by a variety of methods, such as vacuum evaporation, solution spin coating, screen printing, inkjet printing.

[0102] In some embodiments, the organic light-emitting device 100 further includes a protective layer and a packaging layer disposed on the side of the cover layer 30 away from the second electrode 12.

[0103] In some embodiments, the protective layer is disposed on the cover layer 30. The protective layer contains lithium fluoride (LiF). The thickness of the protective layer depends on the material used, and generally, the thickness range of the protective layer is 20 nm - 400 nm, preferably 30 nm - 200 nm, and more preferably 40 nm - 100 nm.

[0104] In some embodiments, the packaging layer is disposed on the protective layer. The packaging layer is a protective structure for preventing external substances such as moisture and oxygen from entering the organic layer in the organic light-emitting device 100. The packaging layer is a multi-layer thin film covering the entire surface of the organic layer, the cover layer, and the protective layer. The packaging layer includes a first packaging layer disposed on the protective layer, a second packaging layer disposed on the first packaging layer, and a third packaging layer disposed on the second packaging layer; the first packaging layer is an inorganic layer; the second packaging layer is an organic layer; the third packaging layer is an inorganic layer; the inorganic layer contains at least one selected from the group consisting of Al2O3, SiOxNy, TiO2, SiOx, and SiNx, where x and y are the same or different, and x and y are independently greater than 0 and less than 10, preferably greater than 0 and less than 5, and most preferably greater than 0 and less than 3. The inorganic layer is prepared by chemical vapor deposition (CVD).

[0105] The organic layer in the encapsulation layer is made of an organic material, and the organic materials for the encapsulation layer of organic electroluminescent devices known in the prior art can be used. For example, the materials of the organic layer may include polydimethylsiloxane (PDMS), polymethylmethacrylate (PMMA), polystyrene (PS), polymer derivatives having a phenol group, acryl-based polymers, imide-based polymers, arylether-based polymers, amide-based polymers, fluorine-based polymers, p-xylene-based polymers, vinylalcohol-based polymers, or mixtures thereof. The thickness of the organic layer is sufficient to cover the inorganic layer, and the organic material of the organic layer is cured into a polymer by UV curing.

[0106] Continuing from the above, the organic light-emitting device 100 is preferably a top-emitting organic electroluminescent device. The organic compound provided in the embodiment of the present application contains tetrahydrocyclobutane dipyrrole tetrone. Therefore, the organic compound has an excellent tetrahydrocyclobutane dipyrrole tetrone structure of "non-conjugated planar connection design", so that the organic compound provided in the present application has a relatively high first singlet excited state energy level and a relatively high glass transition temperature. The reasonable introduction of trifluoromethyl groups can give it a relatively low refractive index. In addition, when the film layer formed by using this organic compound is combined with a high refractive index film layer to form a covering layer and applied to the organic light-emitting device 100, the luminous efficiency and color purity of the device can be significantly improved, and it can be used to improve the viewing angle deviation problem.

[0107] It can be understood that the viewing angle deviation problem mentioned in the embodiment of the present application refers to the gradual change of the emission color when observing the organic light-emitting device 100 at different angles. In the embodiment of the present application, the viewing angle deviation is improved to reduce the angle dependence, and specifically, as the viewing angle of the organic light-emitting device 100 changes, the change trend of the emission color is significantly reduced, and ideally, the emission color does not change. It can be measured by the parameter JNCD (JUST NOTICEABLE COLOR DIFFERENCE). JNCD is the obvious color difference that can be perceived by the human eye. The smaller the JNCD value, the more obvious the effect of improving the viewing angle deviation.

[0108] In addition, the organic light-emitting device 100 provided in the embodiment of the present application can also be used in OLED lighting and display devices.

[0109] In some embodiments, the organic light emission period 100 provided by the embodiments of the present application can be used in fields such as smartphones, tablet computers, etc., the field of smart wearable devices, the field of large-size applications such as televisions, VR, the microdisplay field, and automotive center control screens or automotive tail lights.

[0110] Furthermore, the synthesis method of the organic compound provided by the embodiments of the present application will be described below in conjunction with specific embodiments, but the organic compound provided by the embodiments of the present application is not limited to the following embodiments.

[0111] Synthesis of organic compound M1:

[0112]

[0113] Add compound 1-1 (10 mmol) and compound 1-2 (30 mmol) into a two-necked round-bottom flask, and then add an appropriate amount of xylene solvent to the reaction system. Purge with nitrogen 3 times. Then, heat the above system to 140 °C and stir the reaction overnight. After the reaction is complete, cool the system to room temperature. Filter the reaction system with a Buchner funnel to obtain a crude product filter cake. Further, recrystallize the obtained crude product filter cake with a mixed solvent of toluene and acetonitrile. After filtering and drying the recrystallized product, organic compound M1 is obtained, with a yield of 90.5%, and the mass spectrum m / z [H + = 482.

[0114] Synthesis of organic compound M2:

[0115]

[0116] For the synthesis of organic compound M2, use the reaction process and raw materials of the above organic compound M1, and replace compound 1-2 with compound 2-1 to obtain organic compound M2, with a yield of 86.5%. The mass spectrum m / z [H + = 482.

[0117] Synthesis of organic compound M3:

[0118]

[0119] For the synthesis of organic compound M3, use the above reaction process and raw materials, and replace compound 1-2 with compound 3-1 to obtain organic compound M3, with a yield of 89.2%. The mass spectrum m / z [H + = 618.

[0120] Synthesis of organic compound M4:

[0121]

[0122] The organic compound M4 is obtained by using the above reaction process and raw materials, and replacing compound 1-2 with compound 4-1. Yield: 86.7%. Mass spectrum m / z [H + = 754.

[0123] Synthesis of organic compound M5:

[0124]

[0125] Synthesis of intermediate 5-2:

[0126] Add compound 1-1 (10 mmol) and compound 5-1 (30 mmol) to a two-necked round-bottom flask, and then add an appropriate amount of xylene solvent to the reaction system. Purge with nitrogen 3 times. Then, heat the above system to 140 °C and stir the reaction overnight. After the reaction is complete, cool the system to room temperature. Filter the reaction system with a Buchner funnel to obtain a crude product cake. Further, recrystallize the obtained crude product cake with a mixed solvent of toluene and acetonitrile. After filtering and drying the recrystallized product, intermediate 5-2 is obtained with a yield of 84.5%. Mass spectrum m / z [H + = 640.

[0127] Synthesis of organic compound M5:

[0128] Dissolve compound 5-2 (10 mmol), compound 5-3 (30 mmol), Pd(PPh3)4 (0.1 mmol) and potassium carbonate (30 mmol) in a mixed solvent of 1,4-dioxane and water, and stir at 100 °C for 12 h under a nitrogen atmosphere. After cooling the reaction system to room temperature, remove a part of the solvent using a rotary evaporator, and then extract with dichloromethane and water 3 times. After liquid separation, dry the organic phase by evaporation to obtain a crude product. Recrystallize with a mixed solvent of toluene and acetonitrile. After filtering and drying the recrystallized product, organic compound M5 is obtained with a yield of 81.2%. Mass spectrum m / z [H + = 770.

[0129] Synthesis of organic compound M6:

[0130]

[0131] The organic compound M6 is obtained by using the reaction process and raw materials of the above organic compound M5, and replacing compound 5-3 with compound 6-1. Yield: 80.1%. Mass spectrum m / z [H + = 770.

[0132] Synthesis of organic compound M7:

[0133]

[0134] Intermediate 7-2 was obtained by using the reaction process and raw materials of the above Intermediate 5-2, and replacing compound 5-1 with compound 7-1. Yield: 82.9%. Mass spectrum m / z [H+] = 640.

[0135] Organic compound M7 was obtained by using the reaction process and raw materials of the above Organic compound M5. Yield: 83.3%. Mass spectrum m / z [H + = 770.

[0136] Synthesis of organic compound M8:

[0137]

[0138] Intermediate 7-2 was obtained by using the reaction process and raw materials of the above Intermediate 5-2, and replacing compound 5-1 with compound 7-1. Yield: 82.9%. Mass spectrum m / z [H + = 640.

[0139] Organic compound M8 was obtained by using the reaction process and raw materials of the above Organic compound M5, and replacing compound 5-3 with compound 6-1. Yield: 81.0%. Mass spectrum m / z [H + = 770.

[0140] Synthesis of organic compound M9:

[0141]

[0142] Intermediate 9-2 was obtained by using the reaction process and raw materials of the above Intermediate 5-2, and replacing compound 5-1 with compound 9-1. Yield: 84.0%. Mass spectrum m / z [H + = 640.

[0143] Organic compound M9 was obtained by using the reaction process and raw materials of the above Organic compound M5. Yield: 83.3%. Mass spectrum m / z [H + = 770.

[0144] Synthesis of organic compound M10:

[0145]

[0146] Intermediate 9-2 was obtained by using the reaction process and raw materials of the above Intermediate 5-2, and replacing compound 5-1 with compound 9-1. Yield: 84.0%. Mass spectrum m / z [H + = 640.

[0147] The organic compound M10 uses the reaction process and raw materials of the above-mentioned organic compound M5, replaces compound 5-3 with compound 6-1, to obtain the organic compound M10, yield: 84.1%. Mass spectrometry m / z[H + = 770.

[0148] Synthesis of organic compound M11:

[0149]

[0150] The organic compound M10 uses the reaction process and raw materials of the above-mentioned organic compound M5, replaces compound 5-3 with compound 11-1, to obtain the organic compound M11, yield: 84.9%. Mass spectrometry m / z[H + = 906.

[0151] Synthesis of organic compound M12:

[0152]

[0153] The organic compound M12 uses the reaction process and raw materials of the above-mentioned organic compound, replaces compound 5-1 with compound 7-1, and replaces compound 5-3 with compound 11-1, to obtain the organic compound M12, yield: 85.6%. Mass spectrometry m / z[H + = 906.

[0154] Synthesis of organic compound M13:

[0155]

[0156] The organic compound M13 uses the reaction process and raw materials of the above-mentioned organic compound M5, replaces compound 5-1 with compound 9-1, and replaces compound 5-3 with compound 11-1, to obtain the organic compound M13, yield: 82.6%. Mass spectrometry m / z[H + = 906.

[0157] Synthesis of organic compound M14:

[0158]

[0159] The organic compound M14 uses the reaction process and raw materials of the above-mentioned organic compound M1, replaces compound 1-2 with compound 14-1, to obtain the organic compound M14, yield: 90.5%. Mass spectrometry m / z[H + = 518.

[0160] Synthesis of organic compound M15:

[0161]

[0162] Synthesis of Intermediate 15-2:

[0163] Add Compound 1-1 (10 mmol) and Compound 15-1 (10 mmol) into a two-necked round-bottom flask. Then, add an appropriate amount of toluene solvent to the reaction system. Purge with nitrogen three times. Then, heat the above system to 120 °C and stir the reaction overnight. After the reaction is complete, cool the system to room temperature. Filter the reaction system through a Buchner funnel to obtain a crude product cake. Further, recrystallize the obtained crude product cake with a mixed solvent of toluene and acetonitrile. After filtering and drying the recrystallized product, Intermediate 15-2 is obtained with a yield of 70.8%, and the mass spectrometry m / z [H + = 407.

[0164] Synthesis of Organic Compound M15:

[0165] Add Compound 15-2 (10 mmol) and Compound 15-3 (15 mmol) into a two-necked round-bottom flask. Then, add an appropriate amount of toluene solvent to the reaction system. Purge with nitrogen three times. Then, heat the above system to 120 °C and stir the reaction overnight. After the reaction is complete, cool the system to room temperature. Filter the reaction system through a Buchner funnel to obtain a crude product cake. Further, recrystallize the obtained crude product cake with a mixed solvent of toluene and acetonitrile. After filtering and drying the recrystallized product, Organic Compound M15 is obtained with a yield of 93.3%, and the mass spectrometry m / z [H + = 572.

[0166] Synthesis of Compound M16:

[0167]

[0168] For the synthesis of Intermediate 16-2, use the above reaction procedure and raw materials of Intermediate 15-2, replacing Compound 15-1 with Compound 16-1 to obtain Intermediate 16-2 with a yield of 70.8%, and the mass spectrometry m / z [H + = 407.

[0169] Synthesis of Compound M16:

[0170] Add Compound 16-2 (10 mmol) and Compound 16-3 (15 mmol) into a two-necked round-bottom flask. Then, add an appropriate amount of toluene solvent to the reaction system. Purge with nitrogen three times. Then, heat the above system to 120 °C and stir the reaction overnight. After the reaction is complete, cool the system to room temperature. Filter the reaction system through a Buchner funnel to obtain a crude product cake. Further, recrystallize the obtained crude product cake with a mixed solvent of toluene and acetonitrile. After filtering and drying the recrystallized product, Organic Compound M16 is obtained with a yield of 92.1%, and the mass spectrometry m / z [H+ =532.

[0171] Synthesis of organic compound M17:

[0172]

[0173] The synthesis of intermediate 17-2 uses the reaction process and raw materials of the above intermediate 15-2. Replace compound 15-1 with compound 17-1 to obtain intermediate 17-2 with a yield of 70.8%. Mass spectrometry m / z [H + =407.

[0174] Synthesis of organic compound M17:

[0175] Add compound 17-2 (10 mmol) and compound 17-3 (15 mmol) to a two-necked round-bottom flask. Then add an appropriate amount of toluene solvent to the reaction system. Evacuate and replace with nitrogen 3 times. Then heat the above system to 120 °C and stir the reaction overnight. After the reaction is complete, cool the system to room temperature. Filter the reaction system through a Buchner funnel to obtain a crude product cake. Further, recrystallize the obtained crude product cake with a mixed solvent of toluene and acetonitrile. After filtering and drying the recrystallized product, organic compound M17 is obtained with a yield of 94.2%. Mass spectrometry m / z [H + =510.

[0176] Synthesis of organic compound M18:

[0177]

[0178] The synthesis of intermediate 18-2 uses the reaction process and raw materials of the above intermediate 15-2. Replace compound 15-1 with compound 18-1 to obtain intermediate 18-2 with a yield of 70.8%. Mass spectrometry m / z [H + =407.

[0179] Synthesis of organic compound M18:

[0180] Add compound 18-2 (10 mmol) and compound 18-3 (15 mmol) to a two-necked round-bottom flask. Then add an appropriate amount of toluene solvent to the reaction system. Evacuate and replace with nitrogen 3 times. Then heat the above system to 120 °C and stir the reaction overnight. After the reaction is complete, cool the system to room temperature. Filter the reaction system through a Buchner funnel to obtain a crude product cake. Further, recrystallize the obtained crude product cake with a mixed solvent of toluene and acetonitrile. After filtering and drying the recrystallized product, organic compound M18 is obtained with a yield of 90.8%. Mass spectrometry m / z [H + =564.

[0181] Synthesis of organic compound M19:

[0182]

[0183] The synthesis of intermediate 19-2 uses the reaction process and raw materials of the above intermediate 15-2. Replace compound 15-1 with compound 19-1 to obtain intermediate 19-2, with a yield of 70.8%. Mass spectrometry m / z[H + = 407.

[0184] Synthesis of organic compound M19:

[0185] Add compound 19-2 (10 mmol) and compound 19-3 (15 mmol) to a two-necked round-bottom flask. Then, add an appropriate amount of toluene solvent to the reaction system. Purge with nitrogen 3 times. Then, heat the above system to 120 °C and stir the reaction overnight. After the reaction is complete, cool the system to room temperature. Filter the reaction system with a Buchner funnel to obtain a crude product cake. Further, recrystallize the obtained crude product cake with a mixed solvent of toluene and acetonitrile. After filtering and drying the recrystallized product, organic compound M19 is obtained, with a yield of 87.2%. Mass spectrometry m / z[H + = 744.

[0186] Synthesis of organic compound M20:

[0187]

[0188] The synthesis of intermediate 20-2 uses the reaction process and raw materials of the above intermediate 15-2. Replace compound 15-1 with compound 20-1 to obtain intermediate 20-2, with a yield of 70.8%. Mass spectrometry m / z[H + = 407.

[0189] Synthesis of organic compound M20:

[0190] Add compound 20-2 (10 mmol) and compound 20-3 (15 mmol) to a two-necked round-bottom flask. Then, add an appropriate amount of toluene solvent to the reaction system. Purge with nitrogen 3 times. Then, heat the above system to 120 °C and stir the reaction overnight. After the reaction is complete, cool the system to room temperature. Filter the reaction system with a Buchner funnel to obtain a crude product cake. Further, recrystallize the obtained crude product cake with a mixed solvent of toluene and acetonitrile. After filtering and drying the recrystallized product, organic compound M20 is obtained, with a yield of 87.2%. Mass spectrometry m / z[H + = 648.

[0191] Synthesis of organic compound M21:

[0192]

[0193] The synthesis of intermediate 21-2 adopted the reaction process and raw materials of the above intermediate 15-2. Compound 15-1 was replaced with compound 21-1 to obtain intermediate 21-2, with a yield of 70.8%. The mass spectrometry m / z [H + = 407.

[0194] Synthesis of organic compound M21:

[0195] Compound 21-2 (10 mmol) and compound 21-3 (15 mmol) were added to a two-necked round-bottom flask. Then, an appropriate amount of toluene solvent was added to the reaction system. The system was evacuated and replaced with nitrogen three times. Then, the above system was heated to 121 °C, and the reaction was stirred overnight. After the reaction was complete, the system was cooled to room temperature. The reaction system was filtered by suction using a Buchner funnel to obtain a crude product cake. Further, the obtained crude product cake was recrystallized with a mixed solvent of toluene and acetonitrile. After the recrystallized product was filtered by suction and dried, organic compound M21 was obtained, with a yield of 85.3%. The mass spectrometry m / z [H + = 650.

[0196] Synthesis of organic compound M22:

[0197]

[0198] The reaction process and raw materials of the above organic compound M5 were adopted for organic compound M22. Compound 5-1 was replaced with compound 22-1, and compound 5-3 was replaced with compound 22-3 to obtain organic compound M22, with a yield of 84.9%. The mass spectrometry m / z [H + = 906.

[0199] Synthesis of organic compound M23:

[0200]

[0201] The reaction process and raw materials of the above organic compound M5 were adopted for organic compound M23. Compound 5-1 was replaced with compound 23-1, and compound 5-3 was replaced with compound 23-3 to obtain organic compound M23, with a yield of 87.8%. The mass spectrometry m / z [H + = 814.

[0202] Synthesis of organic compound M24:

[0203]

[0204] The organic compound M24 uses the reaction process and raw materials of the above-mentioned organic compound M5, replaces compound 5-1 with compound 24-1, and replaces compound 5-3 with compound 24-3 to obtain the organic compound M24, with a yield of 83.8%. Mass spectrum m / z[H + = 814.

[0205] Furthermore, the energy levels of the above-mentioned organic compounds can be obtained through quantum calculations. For example, using TD-DFT (time-dependent density functional theory) through Gaussian09W (Gaussian Inc.). The specific simulation method can be referred to WO2011141110. First, use the semi-empirical method "Ground State / DFT / Default Spin / B3LYP / 6-31G(d)" (Charge 0 / Spin Singlet) to optimize the molecular geometry. The energy structure of the organic molecule is calculated by the TD-DFT (time-dependent density functional theory) method "TD-SCF / DFT / Default Spin / B3PW91" and the basis set "6-31G(d)" (Charge 0 / Spin Singlet). Through the above measurement methods, all the test result data are shown in Table 1 below.

[0206] Table 1

[0207]

[0208]

[0209] As can be seen from the data in Table 1 above, compared with compound Ref-01 and compound Ref-02, the organic compounds M1-M24 provided in the embodiments of the present application have higher first singlet excited state energy levels. Therefore, the organic compounds M1-M24 provided in the embodiments of the present application have weak absorption in the visible light band, while showing high absorption performance in the ultraviolet band, which enables it to effectively resist the damage caused by external high-energy light to the inside of the device. At the same time, it has a low refractive index.

[0210] In addition, a differential scanning calorimeter DSC (TA Instruments Co., Ltd., USA, model DSC25) was used to test the samples of compounds M1-M24, Ref-01, and Ref-02 of the present application to determine their glass transition temperatures (Tg). The test results are shown in Table 2.

[0211] Table 2

[0212]

[0213]

[0214] As can be seen from the data in Table 2 above, compared with Compound Ref-01 and Compound Ref-02, the organic compounds M1 to M24 provided in the embodiments of the present application have a higher Tg. When the organic compounds M1 to M24 are used to prepare the organic light-emitting device 100, it helps to improve the device life.

[0215] The following device embodiments are used to further illustrate the effects of the organic compounds provided in the embodiments of the present application as the first sub-layer 31 and applied to OLED devices.

[0216] 1. Materials, equipment, and testing methods used in the embodiments.

[0217] Material sources: Commercially purchased or synthesized by referring to the literature of the prior art.

[0218] The molecular structural formulas of the relevant materials involved in the device are shown below:

[0219]

[0220] Testing equipment: Vacuum evaporation device: A 200*200mm evaporation equipment of Nagatech Industry, Japan.

[0221] Testing method: Determination of current efficiency, CIEx, CIEy, and perceptible color difference (JNCD): Use an IVL (current-voltage-luminance) test system (Suzhou Fushida Scientific Instruments Co., Ltd.), select software EILV20060707, and test the OLED devices in the following device embodiments and device comparative examples. At the same time, obtain data such as the IVL characteristic curve, efficiency-current density relationship curve, and color coordinate position of the device. The test process must be carried out in a dark environment under a masking device. The data under the condition of @10 mA / cm2 shall be used as the standard (that is, the performance values corresponding to when the test current density reaches 10 mA / cm2).

[0222] Structure and manufacturing method of Device Embodiment 1:

[0223] Structure of Device Example 1: Substrate 10 / First Electrode 11 (anode) (Ag (100 nm)) / Hole Injection Layer 21 (HT-1:P-1 = 97:3 mass ratio, thickness 10 nm) / Hole Transport Layer 22 (HT-1, thickness 117 nm) / Electron Blocking Layer 23 (EB-1, thickness 10 nm) / Light Emitting Layer 24 (BH-1:BD-1 = 97:3 mass ratio, thickness 20 nm) / Hole Blocking Layer 25 (HB-1, thickness 8 nm) / Electron Transport Layer 26 (ET-1:LiQ = 1:1 mass ratio, thickness 30 nm) / Electron Injection Layer 27 (LiF, thickness 1 nm) / Second Electrode 12 (cathode) (Mg:Ag = 1:9 mass ratio, thickness 16 nm) / First Sub-layer 31 (Compound 1 of the present invention, thickness 15 nm) / Second Sub-layer 32 (CP-H1, thickness 50 nm).

[0224] Fabrication Method of Device Example 1: The substrate 10 is a transparent glass, the first electrode 11 (anode) is Ag (100 nm). The first electrode 11 (anode) is washed, that is, alkali washing, pure water washing, drying are carried out in sequence, and then ultraviolet-ozone washing is carried out to remove organic residues on the surface of the anode layer. On the first electrode 11 after the above washing, using a vacuum evaporation device, HT-1 and P-1 with a film thickness of 10 nm are evaporated as the hole injection layer 21, and the mass ratio of HT-1 and P-1 is 97:3. Then HT-1 with a thickness of 117 nm is evaporated as the hole transport layer 22. Subsequently, EB-1 with a thickness of 10 nm is evaporated as the electron blocking layer 23. After the evaporation of the above electron blocking material is completed, the light emitting layer 24 of the OLED light emitting device is fabricated. Its structure includes BH-1 used as the host material and BD-1 used as the doping material for the OLED light emitting layer 24. The doping ratio of the doping material is 3% by weight, and the film thickness of the light emitting layer 24 is 20 nm. After the above light emitting layer 24, HB-1 is continuously evaporated with a film thickness of 8 nm as the hole blocking layer 25. On the above hole blocking layer 25, ET-1 and Liq are continuously evaporated, and the mass ratio of ET-1 and Liq is 1:1. The vacuum evaporation film thickness of this material is 30 nm, and this layer is the electron transport layer 26. On the electron transport layer 26, a LiF layer with a film thickness of 1 nm is fabricated through a vacuum evaporation device, and this layer is the electron injection layer 27. On the electron injection layer 27, a Mg:Ag electrode layer with a film thickness of 16 nm is fabricated through a vacuum evaporation device, and the mass ratio of Mg and Ag is 1:9, and this layer is the second electrode 12 (cathode). On the second electrode 12, Compound 1 of the present invention with a vacuum evaporation film thickness of 15 m is used as the first sub-layer 31; on the first sub-layer 31, CPL-1 with a film thickness of 50 nm is continuously vacuum evaporated as the second sub-layer 32.

[0225] Device Example 2: The material of the first sub-layer 31 of the organic light emitting device 100 is changed to organic compound M2.

[0226] Device Example 3: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M3.

[0227] Device Example 4: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M4.

[0228] Device Example 5: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M5.

[0229] Device Example 6: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M6.

[0230] Device Example 7: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M7.

[0231] Device Example 8: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M8.

[0232] Device Example 9: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M9.

[0233] Device Example 10: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M10.

[0234] Device Example 11: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M11.

[0235] Device Example 12: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M12.

[0236] Device Example 13: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M13.

[0237] Device Example 14: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M14.

[0238] Device Example 15: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M15.

[0239] Device Example 16: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M16.

[0240] Device Example 17: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M17.

[0241] Device Example 18: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M18.

[0242] Device Example 19: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M19.

[0243] Device Example 20: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M20.

[0244] Device Example 21: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M21.

[0245] Device Example 22: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M22.

[0246] Device Example 23: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M23.

[0247] Device Example 24: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound M24.

[0248] Device Comparative Example 1: The material of the first sub-layer 31 of the organic light-emitting device 100 is the organic compound M1, and there is no second sub-layer 32.

[0249] Device Comparative Example 2: The organic light-emitting device 100 does not have the first sub-layer 31, and the material of the second sub-layer 32 is CPL-1.

[0250] Device Example 3: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound Ref-01.

[0251] Device Example 4: The material of the first sub-layer 31 of the organic light-emitting device 100 is changed to the organic compound Ref-02.

[0252] The device test results are shown in Table 3 below:

[0253] Table 3

[0254]

[0255]

[0256] As can be seen from the data in Table 3, n1 represents the refractive index of the low refractive index covering layer for light with a wavelength of 460 nm, while n2 represents the refractive index of the high refractive index covering layer for light with a wavelength of 460 nm. Through the analysis of the results of Comparative Examples 1-4 and Examples 1-24, it can be known that when using only the high refractive index or low refractive index covering layer alone, the luminous efficiency of the device is low and the color purity is not good. Further analysis shows that although both a high refractive index and a low refractive index covering layer are provided in Comparative Example 3 and Comparative Example 4, the luminous efficiency of the device is improved, but the color purity is still not ideal. Among them, the blue spectral color coordinates are (x≈0.14, y≈0.08), while the coordinate y of the organic light emitting device 10 prepared from the organic compound provided in the examples of the present application is closer to 0.08. Therefore, when keeping the high refractive index covering layer material unchanged and using the compound of the present application to prepare the low refractive index covering layer, not only can the luminous efficiency of the device be significantly improved, but also the blue light color purity can be significantly enhanced.

[0257] In summary, the organic compound provided in the examples of the present application can be used to prepare a low refractive index covering layer with a relatively high first singlet excited state energy level and a relatively high glass transition temperature (Tg). When jointly forming the covering layer structure of the organic light emitting device with the high refractive index covering layer, the luminous efficiency and blue light color purity of the organic light emitting device 100 can be significantly improved.

[0258] In addition, the examples of the present application also provide a display panel, and the display panel includes the organic light emitting device described in the above examples.

[0259] In summary, the organic compound provided in the examples of the present application contains tetrahydrocyclobutane dipyrrole tetrone. Therefore, the organic compound has an excellent "non-conjugated planar connection design" tetrahydrocyclobutane dipyrrole tetrone structure, making the organic compound provided in the present application have a relatively high first singlet excited state energy level and a relatively high glass transition temperature. The reasonable introduction of the trifluoromethyl group can make it have a relatively low refractive index. In addition, when the film layer formed by using this organic compound is combined with the high refractive index film layer to form a covering layer and applied to the organic light emitting device 100, the luminous efficiency and color purity of the device can be significantly improved, and it can be used to improve the viewing angle deviation problem, and further improve the display effect of the display panel with the organic light emitting device 100.

[0260] In the description of the present application, the terms "first" and "second" are only used for descriptive purposes and cannot be understood as indicating or implying relative importance or implicitly specifying the quantity of the indicated technical features. Thus, the features defined with "first" and "second" may explicitly or implicitly include one or more features. In the description of the present application, the meaning of "a plurality" is two or more unless otherwise specifically defined.

[0261] In the above embodiments, the descriptions of the respective embodiments have their own focuses. For the parts not detailed in a certain embodiment, reference may be made to the relevant descriptions of other embodiments.

[0262] Among the embodiments, implementation manners and related technical features of the present application, they can be combined and replaced with each other without conflict.

[0263] The above are only the preferred embodiments of the present application and do not impose any formal restrictions on the present application. However, any simple modifications, equivalent changes and decorations made to the above embodiments based on the technical essence of the present application without departing from the content of the technical solution of the present application still fall within the scope of the technical solution of the present application.

Claims

1. An organic compound, characterized in that, The organic compound has a structural formula shown in Formula (1): Among them, R1 to R 10 are the same or different and each independently selected from hydrogen, deuterium, halogen, nitro, cyano, substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted fluoroalkyl having 1 to 10 carbon atoms, substituted or unsubstituted fluorocycloalkyl having 1 to 10 carbon atoms, substituted or unsubstituted aryl having 6 to 20 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms, substituted or unsubstituted arylamino having 6 to 20 carbon atoms, substituted or unsubstituted heteroarylamino having 3 to 20 carbon atoms containing at least one heteroatom, and the heteroatom in the heteroaryl or the heteroarylamino is selected from at least one of a nitrogen atom, an oxygen atom, a phosphorus atom, a sulfur atom or a silicon atom; R1 to R 10 contains at least one trifluoromethyl group.

2. The organic compound according to claim 1, wherein R1 to R 10 are the same or different and each independently selected from hydrogen, deuterium, halogen, nitro, cyano, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, fluoromethyl, fluoromethoxy, fluorine-substituted cyclohexyl, methyl, tert-butyl, cyclohexyl, adamantane, and any one of the following groups which may or may not be substituted: wherein, n1 is selected from 1, 2, 3, 4 or 5; The expression of "—" crossing the ring structure indicates that the connection site is at any bonding position on the ring structure; "*" represents the connection site.

3. The organic compound according to claim 1, characterized in that, R1 to R 10 are the same or different and each independently selected from any one of hydrogen, fluorine, nitro, cyano, methyl, trifluoromethyl, phenyl substituted with at least one trifluoromethyl, phenyl substituted with at least one fluorine, cyclohexyl, cyclohexyl substituted with at least one fluorine, dibenzofuranyl, diphenylamino.

4. The organic compound according to claim 1, characterized in that, The organic compound is selected from one of the following compounds:

5. An organic light emitting device, characterized in that, The organic light-emitting device includes: a first electrode; an organic functional layer disposed on one side of the first electrode; a second electrode disposed on the side of the organic functional layer away from the first electrode; a cover layer disposed on the side of the second electrode away from the first electrode; wherein, the material of the cover layer includes at least one organic compound as described in any one of claims 1 to 4.

6. The organic light emitting device according to claim 5, wherein, The cover layer includes a first sub-layer and a second sub-layer stacked, the first sub-layer is between the second electrode and the second sub-layer, and the material of the first sub-layer includes at least one of the organic compounds.

7. The organic light-emitting device according to claim 6, characterized in that, The refractive index of the first sub-layer is less than that of the second sub-layer.

8. The organic light emitting device according to claim 6, characterized in that, The refractive index of the first sub-layer for light with a wavelength of 460 nm is less than or equal to 1.65, and the refractive index of the second sub-layer for light with a wavelength of 460 nm is greater than or equal to 1.

85.

9. The organic light emitting device according to claim 6, wherein The difference between the refractive index of the second sub-layer for light with a wavelength of 460 nm and the refractive index of the first sub-layer for light with a wavelength of 460 nm is greater than or equal to 0.3, and the difference between the refractive index of the first sub-layer for light with a wavelength of 460 nm and the refractive index of the first sub-layer for light with a wavelength of 620 nm is less than or equal to 0.

3.

10. A display panel, characterized in that, The display panel includes the organic light-emitting device as described in any one of claims 5 to 9.

Images