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 conjugate length and electron distribution of molecules are effectively adjusted in a nitrogen atom para-position connection mode, so that a higher first singlet excited state energy level is favorably formed, the structure is also favorable for constructing good coplanarity, and a higher glass transition temperature is further realized; in addition, a benzene ring of the phthalimide is easy to introduce a plurality of functional groups, which is beneficial for obtaining a lower refractive index; when a film layer formed by the organic compound and a high-refractive-index film layer are combined 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 organic light-emitting device can be remarkably improved.

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 significant progress has been made in the process of practical application. Although the research and development of organic electroluminescence technology have advanced rapidly, many challenges still remain, especially the need to improve the External Quantum Efficiency (EQE). For organic light-emitting devices, the luminous quantum efficiency is not only a comprehensive reflection of the device performance but also an important criterion for measuring the device quality.

[0003] Currently, some organic light-emitting materials with excellent performance have been applied in the commercial field. By using specific arylamine derivatives with high refractive indices or materials that meet specific parameter requirements as the cover 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 cover layer. Therefore, in order to further improve the luminous efficiency of organic light-emitting elements without adding too much material, researchers have explored a double-cover-layer structure composed of a low-refractive-index cover layer and a high-refractive-index cover layer. For example, although Samsung's US20210159427A1 patent uses a double-layer cover layer composed of a low-refractive-index material and a high-refractive-index material, the low-refractive-index material used is a coordination compound, and the stability of the coordination bond is poor. This patent only records that the luminous efficiency of the device can be improved, but does not record the impact on the viewing angle deviation of the device. Although Hodogaya's WO2022075396A1 patent also uses a similar double-layer cover 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, and it is easy to spray materials, polluting the evaporation equipment. Moreover, it is easy to crystallize after coating, affecting the device stability, especially the stability of high-temperature devices. And this patent also only records that the luminous efficiency of the device can be improved, but does not record the impact on the viewing angle deviation of the device.

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

[0005] An embodiment of the present application provides 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 viewing angle dependence of the display panel.

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

[0007]

[0008] Wherein, L is selected from a single bond, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted fluorocycloalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylamino group having 3 to 20 carbon atoms;

[0009] R1 and R2 are the same or different and are each independently selected from hydrogen, deuterium, halogen, nitro, cyano, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted fluorocycloalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylamino group having 3 to 20 carbon atoms;

[0010] n1 is selected from 0, 1, 2, 3, or 4;

[0011] n2 is selected from 0, 1, 2, 3, or 4;

[0012] The heteroatoms in the heteroaryl group in L and the heteroatoms in the heteroalkyl group are each independently selected from at least one of nitrogen, oxygen, sulfur, phosphorus, and silicon; the heteroatoms in the heteroaryl group in R1 and the heteroatoms in the heteroalkyl group are each independently selected from at least one of nitrogen, oxygen, sulfur, phosphorus, and silicon; the heteroatoms in the heteroaryl group in R2 and the heteroatoms in the heteroalkyl group are each independently selected from at least one of nitrogen, oxygen, sulfur, phosphorus, and silicon;

[0013] The expression of "—" crossing the ring structure indicates that the bonding site is located at any bonding position on the ring structure.

[0014] According to the above object of the present application, an embodiment of the present application further provides an organic light-emitting device, which includes:

[0015] A first electrode;

[0016] An organic functional layer disposed on one side of the first electrode;

[0017] A second electrode disposed on the side of the organic functional layer away from the first electrode;

[0018] A covering layer disposed on the side of the second electrode away from the organic functional layer;

[0019] Wherein, the material of the covering layer includes at least one of the organic compounds.

[0020] According to the above object of the present application, an embodiment of the present application further provides a display panel, which includes the organic light-emitting device.

[0021] The present application provides an organic compound, an organic light-emitting device and a display panel. In the bisphthalimide structure of the organic compound, the conjugated length and electron distribution of the molecule are effectively adjusted by the way of para-position connection of nitrogen atoms, which helps to form a relatively high first singlet excited state energy level. Moreover, this structure is also beneficial to constructing good coplanarity, and then achieving a relatively high glass transition temperature. In addition, various functional groups are easily introduced into the benzene ring of phthalimide, which helps to obtain a relatively low refractive index. When the film layer formed by 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, the luminous efficiency and color purity of the organic light-emitting device can be significantly improved.

[0022] Other features and advantages of the present application will be described in detail in the following specific implementation part. Description of the Drawings

[0023] 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 following drawings are only some embodiments of the present application. For those skilled in the art, without creative efforts, other drawings can also be obtained based on these drawings.

[0024] In order to more fully 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.

[0025] Figure 1The first structural schematic diagram of the organic light-emitting device provided by the embodiment of the present application;

[0026] Figure 2 The second structural schematic diagram of the organic light-emitting device provided by the embodiment of the present application;

[0027] Figure 3 The third structural schematic diagram of the organic light-emitting device provided by the embodiment of the present application.

[0028] Explanation of reference numerals:

[0029] 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. Covering layer; 31. First sub-layer; 32. Second sub-layer. Detailed implementation manners

[0030] In the whole specification, unless explicitly described to the contrary, "including" any component will be understood to implicitly include other elements, rather than excluding any other elements. In addition, it should be understood that throughout the specification, when an element such as a layer, film, region or substrate is referred to as being "on" or "above" another element, it may be "directly on" the other element, or there may also be an intermediate element. Additionally, "on" or "above" means located above the target part, and does not necessarily mean located above in the direction of gravity.

[0031] In this article, "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.

[0032] In this article, 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 an aryl group having 6 to 20 carbon atoms may include phenyl, biphenyl, phenanthryl, terphenyl, naphthyl, phenanthryl, benzo[ghi]perylenyl, 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.

[0033] 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.

[0034] The alkyl group having 1 to 10 carbon atoms (including linear alkyl groups and branched alkyl groups) as 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.

[0035] The halogen atom as described in the present invention refers to a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0036] 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 (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) in each case.

[0037] 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.

[0038] "Aryleneamino" refers to a divalent group of an arylamino system, and "heteroaryleneamino" refers to a divalent group of a heteroarylamino system.

[0039] "Substituted or unsubstituted", the "substitution" means that a hydrogen atom in the structure can be further substituted by other groups.

[0040] An embodiment of the present application provides an organic compound having a structural formula as shown in Formula (1):

[0041]

[0042] wherein, L is selected from a single bond, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted fluorocycloalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylamino group having 3 to 20 carbon atoms;

[0043] R1 and R2 are the same or different and are each independently selected from hydrogen, deuterium, halogen, nitro, cyano, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted fluorocycloalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylamino group having 3 to 20 carbon atoms;

[0044] n1 is selected from 0, 1, 2, 3 or 4;

[0045] n2 is selected from 0, 1, 2, 3 or 4;

[0046] The heteroatoms in the heteroaryl group in L and the heteroatoms in the heteroalkyl group are selected from at least one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, and a silicon atom; the heteroatoms in the heteroaryl group in R1 and the heteroatoms in the heteroalkyl group are selected from at least one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, and a silicon atom; the heteroatoms in the heteroaryl group in R2 and the heteroatoms in the heteroalkyl group are selected from at least one of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, and a silicon atom;

[0047] The expression of "—" crossing the ring structure indicates that the connection site is at any bonding position on the ring structure.

[0048] In the process of implementation and application, the organic compound provided by the embodiment of the present application has a bisphthalimide structure, effectively adjusting the conjugate length and electron distribution of the molecule by the way of para-position connection of nitrogen atoms, thus contributing to the formation of a relatively high first singlet excited state energy level, and this structure is also beneficial to constructing good coplanarity, and then achieving a relatively high glass transition temperature; in addition, the benzene ring of phthalimide is easy to introduce various functional groups, which helps to obtain a relatively low refractive index; when the film layer formed by the organic compound is combined with a high refractive index film layer to form a covering layer and applied to an organic light-emitting device, the luminous efficiency and color purity of the organic light-emitting device can be significantly improved.

[0049] It should be noted that in L, R1, and R2, the heteroatoms in the heteroaryl group and the heteroalkyl group described in the above embodiments are independently selected from one or more of a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, and a silicon atom.

[0050] In some embodiments, L is selected from a single bond or any one of the following structures:

[0051]

[0052]

[0053]

[0054] Among them, n3 is selected from 0, 1, 2, 3, 4, or 5; n4 is selected from 0, 1, 2, 3, or 4; n5 is selected from 0, 1, 2, 3, or 4; n6 is selected from 0, 1, 2, 3, or 4; n7 is selected from 0, 1, 2, 3, or 4; n8 is selected from 0, 1, 2, 3, or 4; n9 is selected from 0, 1, 2, 3, or 4; n 10 is selected from 0, 1, 2, 3, 4, 5, or 6; n 11 is selected from 0, 1, 2, 3, 4, or 5; n 12 is selected from 0, 1, 2, 3, 4, or 5; n 13 is selected from 0, 1, 2, 3, 4, or 5; n 14Selected from 0, 1, 2, 3, 4 or 5; n 15 Selected from 0, 1, 2, 3 or 4.

[0055] * represents a linking site.

[0056] In some embodiments, L is selected from a single bond or any one of the following structures:

[0057]

[0058] It can be understood that in the embodiments of the present application, the expression of the ring structure crossed by “—” indicates that the linking site is located at any bond-forming position on the ring structure; “*” represents a linking site.

[0059] In some embodiments, R1 and R2 are the same or different and are independently selected from hydrogen, protium, deuterium, tritium, halogen, nitro, cyano, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, fluoromethyl, fluoromethoxy, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted diphenylamine, substituted or unsubstituted terphenyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted benzo[a]phenanthrenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furyl, substituted or unsubstituted naphtho[2,3-b]furan-2-yl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted N-biphenylcarbazolyl, substituted or unsubstituted N-naphthylcarbazolyl, substituted or unsubstituted N-dibenzofuranylcarbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted cinnolinyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted naphthofuran, substituted or unsubstituted naphthothiophene, at least one of which.

[0060] In some embodiments, R1 and R2 are the same or different and are independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzophenanthrene, substituted or unsubstituted pyridyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furyl, substituted or unsubstituted naphthofuranophenyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted dibenzofuryl, substituted or unsubstituted fluorenyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted N-biphenylcarbazolyl, substituted or unsubstituted N-naphthylcarbazolyl, substituted or unsubstituted N-dibenzofurylcarbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted naphthofuryl, substituted or unsubstituted naphthothienyl, at least one of which.

[0061] It should be noted that the substituents in the substituted or unsubstituted of R1 and R2 are selected from hydrogen, deuterium, halogen, cyano, nitro, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, fluoromethyl, fluoromethoxy, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, trifluoromethylbenzene, bis(trifluoromethyl)benzene, trifluoromethylbiphenyl, bis(trifluoromethyl)biphenyl, naphthyl, biphenyl, pyridyl, at least one of which.

[0062] In some embodiments, R1 and R2 are the same or different and are independently selected from deuterium, fluorine, cyano, nitro, methyl, cyclohexyl, trifluoromethyl, phenyl substituted with at least one trifluoromethyl, phenyl substituted with at least one fluorine, diphenylamine group substituted with at least one trifluoromethyl, dibenzofuryl, N-phenyl-3-dibenzofurylamine group or tetrahydropyranyl, etc.

[0063] In some embodiments, the organic compound is selected from any one of the following compounds:

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

[0076]

[0077] Continuing from the above, the organic compound provided in the embodiment of the present application has a bis-phthalimide structure, effectively regulating the conjugation length and electron distribution of the molecule by the para-position connection of nitrogen atoms, thereby contributing to the formation of a relatively high first singlet excited state energy level. Moreover, this structure is also conducive to constructing good coplanarity, and further achieving a relatively high glass transition temperature. In addition, various functional groups are easily introduced into the benzene ring of phthalimide, which helps to obtain a relatively low refractive index. When the film layer formed by the organic compound is combined with a high refractive index film layer to form a cover layer and applied to an organic light-emitting device, the luminous efficiency and color purity of the organic light-emitting device can be significantly improved.

[0078] Further, please refer to Figure 1 , the 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 cover layer 30.

[0079] 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 cover layer 30 is disposed on the side of the second electrode 12 away from the organic functional layer 20.

[0080] Further, the material of the cover layer 30 includes at least one of the organic compounds as described in the above embodiments.

[0081] 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.

[0082] 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.

[0083] It can be understood 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.

[0084] 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 smoothnesses, and waterproof properties, and are used in different directions according to the properties of the substrates.

[0085] 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.

[0086] 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.

[0087] 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.

[0088] In some embodiments, the thickness range of the organic functional layer 20 is 50 nm - 1000 nm.

[0089] 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. 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.

[0090] The charge generation material can be a p-dopant. Non-limiting compounds of p-dopants include: 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-trimethylenetri(cyanomethylene))tris(2,3,5,6-tetrafluorobenzyl); or metal oxides such as tungsten oxide and molybdenum oxide, but are not limited thereto.

[0091] 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 conducive 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 conducive to hole transport and reduces the application power of the device; 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'-biphenyl]-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.

[0092] 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 materials can be pure fluorescent materials, thermally activated delayed fluorescence (TADF) materials or phosphorescent materials, or combinations of different fluorescent materials, TADF materials and phosphors. 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 emitter can be selected from the following various structures:

[0093] (1) A single organic light-emitting layer material;

[0094] (2) Any combination of a blue organic light-emitting layer material and any one of a green, yellow or red light-emitting layer material, regardless of the order;

[0095] (3) Any combination of a blue organic light-emitting layer material and any two of a green, yellow or red light-emitting layer material, regardless of the order;

[0096] (4) Horizontally arranged blue organic light-emitting layer material, green organic light-emitting layer material, and red organic light-emitting layer material.

[0097] In order to adjust the effective combination of carrier charges in the light-emitting layer 24, the film thickness of the light-emitting layer 24 constituting the OLED light-emitting body can be arbitrarily adjusted as needed, or light-emitting layers of different colors can be alternately stacked and combined as needed. Additionally, charge blocking layers with different functional uses can be added to the film layers adjacent to the light-emitting layer 24.

[0098] 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, i.e., 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.

[0099] 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 characteristics 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 naphthyl perylene, carbodiimide, fluorene derivatives, anthraquinone dimethane derivatives, anthrone derivatives, stilbenylpyrazine derivatives, silole derivatives, phenanthroline derivatives, or imidazopyridine derivatives, etc.

[0100] 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 various methods, such as vacuum evaporation, solution spin coating, screen printing, inkjet printing, etc.

[0101] 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. Also, 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 to Mg can be from 90:10 to 10:90. Alternatively, 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. Thus, 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.

[0102] In some embodiments, the second electrode 12 can be prepared by, for example, vacuum evaporation.

[0103] It should be noted that the first electrode 11 can be one of the anode or the 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 the anode and the second electrode 12 as the cathode as an example for description.

[0104] 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.

[0105] 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.

[0106] Among them, the material of the first sub-layer 31 includes at least one of the organic compounds as described in the above embodiments.

[0107] In some embodiments, the refractive index of the material of the first sub-layer 31 is less than that 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, and 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. Moreover, 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.

[0108] Further, 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;

[0109] 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.

[0110] In some embodiments, the total film thickness of the covering layer 30 ranges from 15 nm to 300 nm, more preferably from 30 nm to 200 nm, still more preferably from 40 nm to 100 nm, and most preferably from 50 nm to 80 nm; the film thickness of the first sub-layer 31 is from 1 nm to 150 nm, preferably from 5 nm to 100 nm, more preferably from 10 nm to 50 nm; and the film thickness of the second sub-layer 32 is from 1 nm to 150 nm, preferably from 10 nm to 100 nm, more preferably from 20 nm to 80 nm.

[0111] 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.

[0112] 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.

[0113] 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:

[0114]

[0115] In some embodiments, the total film thickness of the covering 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.

[0116] 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.

[0117] 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.

[0118] 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.

[0119] 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.

[0120] 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.

[0121] 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 is generally in the range of 20 nm - 400 nm, preferably 30 nm - 200 nm, and more preferably 40 nm - 100 nm.

[0122] 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 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).

[0123] The organic layer in the encapsulation layer is made of an organic material, and organic materials known in the prior art for the encapsulation layer of organic electroluminescent devices 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.

[0124] Continuing from the above, the organic light-emitting device 100 is preferably a top-emitting organic electroluminescent device. The organic compound provided in the embodiments of the present application has a bisphthalimide structure, and effectively adjusts the conjugation length and electron distribution of the molecule by the para-linkage mode of nitrogen atoms, thereby contributing to the formation of a relatively high first singlet excited state energy level. Moreover, this structure is also beneficial to constructing good coplanarity, and then achieving a relatively high glass transition temperature. In addition, various functional groups are easily introduced into the benzene ring of phthalimide, which helps to obtain a relatively low refractive index. When a film layer formed of this organic compound is combined with a high refractive index film layer to form a cover layer and applied to an organic light-emitting device, the luminous efficiency and color purity of the organic light-emitting device can be significantly improved, and it can be used to improve the viewing angle dependence problem.

[0125] It can be understood that the viewing angle dependence problem mentioned in the embodiments 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 embodiments of the present application, improving the viewing angle dependence to reduce the angle dependence is specifically manifested in that 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 dependence.

[0126] In addition, the organic light-emitting device 100 provided by the embodiments of the present application can also be used in OLED lighting and display devices.

[0127] In some embodiments, the organic light-emitting period 100 provided by the embodiments of the present application can be used in fields such as smartphones, tablets, etc., the field of smart wearable devices, large-size application fields such as TVs, VR, the microdisplay field, and automotive center control screens or automotive tail lights.

[0128] 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.

[0129] The synthesis route of organic compound M1 is as follows:

[0130]

[0131] Add compound 1-1 (10 mmol) and compound 1-2 (10 mmol) to a two-necked round-bottom flask. 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 (12 hours). 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 M1 is obtained as a white solid, with a molar amount of 8.35 mmol and a yield of 83.5%. The mass spectrum m / z [H + = 504.

[0132] The synthesis route of organic compound M2 is as follows:

[0133]

[0134] The synthesis method of organic compound M2 refers to the synthesis operation steps of the above compound M1. Replace compound 1-1 with compound 2-1. The yield of organic compound M2: 81.9%. The mass spectrum m / z [H + = 572.

[0135] The synthesis route of organic compound M3 is as follows:

[0136]

[0137] The synthesis method of organic compound M3 refers to the synthesis operation steps of the above compound M1. Replace compound 1-2 with compound 3-1. The yield of organic compound M3: 85.1%. The mass spectrum m / z [H + = 562.

[0138] The synthetic route of organic compound M4 is as follows:

[0139]

[0140] The synthetic method of organic compound M4 refers to the synthetic operation steps of the above-mentioned compound M1. Replace compound 1-1 with compound 2-1 and compound 1-2 with compound 3-1. The yield of organic compound M4: 82.0%. Mass spectrometry m / z [H + = 698.

[0141] The synthetic route of organic compound M5 is as follows:

[0142]

[0143] Synthesis of intermediate 5-3

[0144] Dissolve compound 5-1 (10 mmol), compound 5-2 (10 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 using a mixed solvent of toluene and acetonitrile. After filtering and drying the recrystallized product, intermediate 5-3 is obtained as a white solid, with a molar amount of 8.42 mmol and a yield of 84.2%. Mass spectrometry m / z [H + = 360.

[0145] The synthetic method of the second step of organic compound M5 refers to the synthetic operation steps of the above-mentioned compound M1. Replace compound 1-1 with intermediate 5-3. The yield of organic compound M5: 82.1%. Mass spectrometry m / z [H + = 792.

[0146] The synthetic route of organic compound M6 is as follows:

[0147]

[0148]

[0149] The synthetic method of the first step of organic compound M6 refers to the synthesis of intermediate 5-3, with a yield: 82.9%. Mass spectrometry m / z [H+] = 360. The synthetic method of the second step of organic compound M6 refers to the synthetic operation steps of the second step of the above-mentioned compound M5. Replace compound 1-2 with compound 6-1. The yield of organic compound M6: 84.9%. Mass spectrometry m / z [H + = 850.

[0150] The synthetic route of organic compound M7 is as follows:

[0151]

[0152] For the first step of synthesizing organic compound M7, refer to the synthesis of intermediate 5-3, yield: 81.5%. Mass spectrum m / z[H+]=360.

[0153] For the second step of synthesizing organic compound M7, refer to the synthetic operation steps of the second step of the above compound M5, replace compound 1-2 with compound 3-1, yield of organic compound M7: 86.1%. Mass spectrum m / z[H + =850.

[0154] The synthetic route of organic compound M8 is as follows:

[0155]

[0156] For the synthesis of intermediate 8-2, refer to the synthetic operation steps of the above compound M1, replace compound 1-1 with compound 8-1, yield of intermediate 8-2: 82.1%. Mass spectrum m / z[H + =526.

[0157] Synthesis of organic compound M8

[0158] Dissolve intermediate 8-2 (10 mmol), compound 8-3 (10 mmol), Pd2(dba)3 (0.1 mmol), X-Phos (0.2 mmol) and sodium tert-butoxide (30 mmol) in xylene, stir at 140 °C for 8 h under a nitrogen atmosphere. After cooling the reaction system to room temperature, use a rotary evaporator to evaporate a part of the solvent. Then, extract 3 times with dichloromethane and water. After drying the organic phase by evaporation, obtain the crude product. Further purify the crude product by recrystallization with toluene to obtain organic compound M8, yield: 83.6%. Mass spectrum m / z[H + =1246.

[0159] The synthetic route of organic compound M9 is as follows:

[0160]

[0161]

[0162] For the synthesis of intermediate 9-1, refer to the synthetic operation steps of the above compound M1, replace compound 1-1 with compound 8-1, replace compound 1-2 with compound 6-1, yield of intermediate 9-1: 85.3%. Mass spectrum m / z[H +=532。

[0163] The synthesis method of organic compound M9 refers to the synthesis operation steps of the above-mentioned compound M8, replacing intermediate 8-2 with intermediate 9-1, yield: 81.5%. Mass spectrometry m / z [H + =1252。

[0164] The synthesis route of organic compound M10 is as follows:

[0165]

[0166] The synthesis method of intermediate 10-1 refers to the synthesis operation steps of the above-mentioned compound M1, replacing compound 1-1 with compound 8-1 and compound 1-2 with compound 3-1. The yield of intermediate 10-1: 83.1%. Mass spectrometry m / z [H + =584。

[0167] The synthesis method of organic compound M10 refers to the synthesis operation steps of the above-mentioned compound M8, replacing intermediate 8-2 with intermediate 10-1. The yield of organic compound M10: 82.8%. Mass spectrometry m / z [H + =1304。

[0168] The synthesis route of organic compound M11 is as follows:

[0169]

[0170] The synthesis method of intermediate 11-3 refers to the synthesis operation steps of the above-mentioned intermediate 5-3, replacing compound 5-1 with compound 11-1 and compound 5-2 with compound 11-2. The yield of intermediate 11-3: 84.2%. Mass spectrometry m / z [H + =360。

[0171] The synthesis method of organic compound M11 refers to the synthesis operation steps of the above-mentioned organic compound M5, replacing intermediate 5-3 with intermediate 11-3 and compound 1-2 with compound 11-4. The yield of organic compound M11: 85.8%. Mass spectrometry m / z [H + =716。

[0172] The synthesis route of organic compound M12 is as follows:

[0173]

[0174]

[0175] The synthesis method of intermediate 12-3 refers to the synthesis operation steps of intermediate 5-3 above. Replace compound 5-1 with compound 12-1 and compound 5-2 with compound 12-2. The yield of intermediate 12-3: 82.5%. Mass spectrometry m / z [H + = 360.

[0176] The synthesis method of organic compound M12 refers to the synthesis operation steps of organic compound M5 above. Replace intermediate 5-3 with intermediate 12-3 and compound 1-2 with compound 12-4. The yield of organic compound M12: 81.0%. Mass spectrometry m / z [H + = 730.

[0177] The synthesis route of organic compound M13 is as follows:

[0178]

[0179] The synthesis method of intermediate 13-3 refers to the synthesis operation steps of intermediate 5-3 above. Replace compound 5-1 with compound 13-1 and compound 5-2 with compound 13-2. The yield of intermediate 13-3: 84.2%. Mass spectrometry m / z [H + = 360.

[0180] The synthesis method of organic compound M13 refers to the synthesis operation steps of organic compound M5 above. Replace intermediate 5-3 with intermediate 13-3 and compound 1-2 with compound 13-4. The yield of organic compound M13: 83.2%. Mass spectrometry m / z [H + = 732.

[0181] The synthesis route of organic compound M14 is as follows:

[0182]

[0183] The synthesis method of intermediate 14-3 refers to the synthesis operation steps of intermediate 5-3 above. Replace compound 5-1 with compound 14-1 and compound 5-2 with compound 14-2. The yield of intermediate 14-3: 84.2%. Mass spectrometry m / z [H + = 360.

[0184] The synthesis method of organic compound M14 refers to the synthesis operation steps of organic compound M5 above. Replace intermediate 5-3 with intermediate 14-3 and compound 1-2 with compound 14-4. The yield of organic compound M14: 86.1%. Mass spectrometry m / z [H + = 882.

[0185] The synthesis route of organic compound M15:

[0186]

[0187]

[0188] For the synthesis method of Intermediate 15-3, refer to the synthesis operation steps of Intermediate 5-3 above. Replace Compound 5-1 with Compound 15-1 and Compound 5-2 with Compound 15-2. The yield of Intermediate 15-3: 82.5%. Mass spectrometry m / z [H + = 360.

[0189] For the synthesis method of Organic Compound M15, refer to the synthesis operation steps of Organic Compound M5 above. Replace Intermediate 5-3 with Intermediate 15-3 and Compound 1-2 with Compound 15-4. The yield of Organic Compound M15: 78.1%. Mass spectrometry m / z [H + = 866.

[0190] The synthesis route of Organic Compound M16 is as follows:

[0191]

[0192] For the synthesis method of Intermediate 16-3, refer to the synthesis operation steps of Intermediate 5-3 above. Replace Compound 5-1 with Compound 16-1 and Compound 5-2 with Compound 16-2. The yield of Intermediate 16-3: 82.5%. Mass spectrometry m / z [H + = 360.

[0193] For the synthesis method of Organic Compound M16, refer to the synthesis operation steps of Organic Compound M5 above. Replace Intermediate 5-3 with Intermediate 16-3 and Compound 1-2 with Compound 16-4. The yield of Organic Compound M16: 78.1%. Mass spectrometry m / z [H + = 866.

[0194] The synthesis route of Organic Compound M17 is as follows:

[0195]

[0196] For the synthesis method of Organic Compound M17, refer to the synthesis operation steps of Compound M1 above. Replace Compound 1-1 with Compound 17-1 and Compound 1-2 with Compound 17-2. The yield of the organic compound: 84.2%. Mass spectrometry m / z [H + = 376.

[0197] The synthesis route of Organic Compound M18 is as follows:

[0198]

[0199] The synthesis method of organic compound M18 refers to the above synthetic operation steps of organic compound M1. Replace compound 1-1 with compound 18-1 and compound 1-2 with compound 18-2. The yield of organic compound M18: 83.7%. Mass spectrometry m / z [H + = 570.

[0200] The synthetic route of organic compound M19 is as follows:

[0201]

[0202] The synthesis method of organic compound M19 refers to the above synthetic operation steps of organic compound M1. Replace compound 1-1 with compound 19-1 and compound 1-2 with compound 19-2. The yield of organic compound M19: 73.5%. Mass spectrometry m / z [H + = 468.

[0203] Synthesis of organic compound M20:

[0204]

[0205] The synthesis method of organic compound M20 refers to the above synthetic operation steps of organic compound M1. Replace compound 1-1 with compound 20-1 and compound 1-2 with compound 20-2. The yield of organic compound M20: 82.5%. Mass spectrometry m / z [H + = 548.

[0206] Synthesis of organic compound M21:

[0207]

[0208] The synthesis method of organic compound M21 refers to the above synthetic operation steps of organic compound M1. Replace compound 1-1 with compound 21-1 and compound 1-2 with compound 21-2. The yield of organic compound M1: 85.1%. Mass spectrometry m / z [H + = 424.

[0209] The synthetic route of organic compound M22 is as follows:

[0210]

[0211] The synthesis method of organic compound M22 refers to the above synthetic operation steps of organic compound M1. Replace compound 1-1 with compound 22-1 and compound 1-2 with compound 22-2. The yield of organic compound M22: 86.4%. Mass spectrometry m / z [H +=532。

[0212] The synthetic route of organic compound M23 is as follows:

[0213]

[0214] The synthetic method of organic compound M23 refers to the synthetic operation steps of the above-mentioned organic compound M1. Replace compound 1-1 with compound 23-1 and compound 1-2 with compound 23-2. The yield of organic compound M23: 84.3%. Mass spectrum m / z [H + =536。

[0215] Synthesis of organic compound M24:

[0216]

[0217] The synthetic method of intermediate 24-3 refers to the synthetic operation steps of the above-mentioned organic compound M1. Replace compound 1-1 with compound 24-1 and compound 1-2 with compound 24-2. The yield of intermediate 24-3: 82.1%. Mass spectrum m / z [H + =526。

[0218] The synthetic method of organic compound M24 refers to the synthetic operation steps of the above-mentioned intermediate 5-3. Replace compound 5-1 with compound 24-4 and compound 5-2 with intermediate 24-3. The yield of organic compound M24: 84.8%. Mass spectrum m / z [H + =700。

[0219] The synthetic route of organic compound M25 is as follows:

[0220]

[0221]

[0222] The synthetic method of intermediate 25-3 refers to the synthetic operation steps of the above-mentioned compound M1. Replace compound 1-1 with compound 25-1 and compound 1-2 with compound 25-2. The yield of intermediate 25-3: 81.1%. Mass spectrum m / z [H + =526。

[0223] The synthetic method of compound M25 refers to the synthetic operation steps of the above-mentioned intermediate 5-3. Replace compound 5-1 with compound 25-4 and compound 5-2 with intermediate 25-3. The yield of organic compound M25: 86.2%. Mass spectrum m / z [H + =882。

[0224] The synthetic route of organic compound M26 is as follows:

[0225]

[0226] For the synthesis method of intermediate 26-3, refer to the synthesis of intermediate 5-3. Replace compound 5-1 with compound 26-1 and compound 5-2 with compound 26-2 to obtain intermediate 26.3, and the yield of intermediate 26-3 is 85.2%. Mass spectrum m / z[H + = 314.

[0227] For the synthesis method of organic compound M26, refer to the second-step synthesis operation procedure of the above compound M5. Replace compound 1-2 with compound 3-1 to obtain organic compound M26, and the yield of organic compound M26 is 83.6%. Mass spectrum m / z[H + = 758.

[0228] Energy structure of organic compounds

[0229] The energy levels of organic materials 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 found in 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 test result data are shown in Table 1 below.

[0230] Table 1

[0231] organic compound S1 organic compound S1 M1 4.60 M15 4.66 M2 4.62 M16 4.71 M3 4.77 M17 4.80 M4 4.85 M18 4.65 M5 4.64 M19 4.69 M6 4.64 M20 4.74 M7 4.82 M21 4.64 M8 4.53 M22 4.59 M9 4.52 M23 4.69 M10 4.71 M24 4.72 M11 4.62 M25 4.65 M12 4.63 M26 4.69 M13 4.68 Ref-01 3.56 M14 4.65

[0232] According to the data in Table 1, compared with compound Ref-01, the organic compounds M1 to M26 in the examples of this application exhibit higher first singlet excited state energy levels. It can be seen that the organic compounds M1 to M26 provided in the examples of this application have relatively weak absorption in the visible light band, while having strong absorption ability in the ultraviolet band. This characteristic enables them to effectively resist the possible damage to the inside of the device caused by external high-energy light.

[0233] Tg test of organic compounds

[0234] The samples of organic compounds M1 to M26 and Ref-01 provided in the embodiments of the present application were tested using a differential scanning calorimeter DSC (TA Instruments, Inc., USA, model DSC25) to determine their glass transition temperatures (T g ), and the test results are shown in Table 2.

[0235] Table 2

[0236] organic compound Tg (°C) organic compound Tg (°C) M1 116 M15 122 M2 119 M16 121 M3 118 M17 120 M4 120 M18 127 M5 123 M19 129 M6 125 M20 130 M7 129 M21 132 M8 124 M22 128 M9 126 M23 126 M10 124 M24 134 M11 125 M25 138 M12 121 M26 132 M13 125 Ref-01 90 M14 120

[0237] The data in Table 2 show that, compared with compound Ref-01, the organic compounds M1 to M26 provided in the embodiments of the present application have higher glass transition temperatures (T g ). When the organic compounds M1 to M26 are applied to the preparation of organic light-emitting devices, the service life of the devices can be significantly improved.

[0238] Device Embodiment

[0239] The following device embodiments are used to further illustrate the beneficial technical effects of the compounds of the present invention when applied as the first covering layer in OLED devices.

[0240] 1. Materials, equipment, and test methods used in the embodiments

[0241] Source of materials: Commercially purchased or synthesized by referring to the literature of the prior art.

[0242] The molecular structural formulas of the relevant materials involved in the devices are as follows:

[0243]

[0244] Test equipment: Vacuum evaporation device: 200*200mm evaporation equipment of Nagatech Co., Ltd., Japan.

[0245] Test method: Determination of current efficiency, CIEx, CIEy, and perceptible color difference (JNCD): Using an IVL (current-voltage-luminance) test system (Fosdick Scientific Instruments Co., Ltd., Suzhou), selecting software EILV20060707, testing the OLED devices in the following device embodiments and device comparative examples, and simultaneously obtaining 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. Based on the data under the condition of @10 mA / cm 2 (that is, the corresponding performance values when the test current density reaches 10 mA / cm 2 ).

[0246] Structure and manufacturing method of Device Embodiment 1:

[0247] The structure of Device Example 1 is as follows Figure 3 shown: Substrate layer / 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 (the compound 1 of the present invention, thickness 15 nm) / Second sub-layer 32 (CP-H1, thickness 50 nm).

[0248] Fabrication method of Device Example 1: The transparent substrate layer is 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, and 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 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 by 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 by 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, the organic compound M1 provided in the embodiment of the present application 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.

[0249] Device Example 2: The material of the first sub-layer 31 in the organic light-emitting device 100 is changed to organic compound M2.

[0250] Device Example 3: The material of the first sub-layer 31 in the organic light-emitting device 100 is changed to organic compound M3.

[0251] Device Example 4: The material of the first sub-layer 31 in the organic light-emitting device 100 is changed to organic compound M4.

[0252] Device Example 5: The material of the first sub-layer 31 in the organic light-emitting device 100 is changed to organic compound M5.

[0253] Device Example 6: The material of the first sub-layer 31 in the organic light-emitting device 100 is changed to organic compound M6.

[0254] Device Example 7: The material of the first sub-layer 31 in the organic light-emitting device 100 is changed to organic compound M7.

[0255] Device Example 8: The material of the first sub-layer 31 in the organic light-emitting device 100 is changed to organic compound M8.

[0256] Device Example 9: The material of the first sub-layer 31 in the organic light-emitting device 100 is changed to organic compound M9.

[0257] Device Example 10: The material of the first sub-layer 31 in the organic light-emitting device 100 is changed to organic compound M10.

[0258] And so on, for Device Examples 11 to 26: The material of the first sub-layer 31 in the organic light-emitting device 100 is changed to organic compounds M11 to M26.

[0259] Device Comparative Example 1: The organic light-emitting device 100 has only the first sub-layer 31 and no second sub-layer 32; and the material of the first sub-layer 31 in the organic light-emitting device 100 is changed to organic compound M1.

[0260] Device Comparative Example 2: The organic light-emitting device 100 has no first sub-layer 31 and only has the second sub-layer 32 (CPL-1).

[0261] Device Example 3: The material of the first sub-layer 31 in the organic light-emitting device 100 is changed to organic compound Ref-01.

[0262] The device test results are shown in Table 3 below:

[0263] Table 3

[0264]

[0265]

[0266]

[0267] Table 3 data shows that n1 represents the refractive index of the first sub-layer 31 for light with a wavelength of 460 nm, and n2 represents the refractive index of the second sub-layer 32 for light with a wavelength of 460 nm. From the results of Device Comparative Example 1, Device Comparative Example 2, and Device Example 1, when only a single high-refractive-index or low-refractive-index covering layer is used, the luminous efficiency of the device is poor and the color purity is not ideal. Further analysis of the results of Device Examples 1 to 26 provided in the embodiments of the present application and Device Comparative Example 3 shows that although Device Comparative Example 3 uses a combination of high-refractive-index and low-refractive-index covering layers, although the luminous efficiency is improved, the color purity still does not meet the expectations. However, when the material of the high-refractive-index covering layer remains unchanged and the organic compound provided in the embodiments of the present application is used to prepare the low-refractive-index covering layer, both the luminous efficiency and color purity of the device are significantly improved; for example, the blue spectral color coordinates are (x≈0.14, y≈0.08), and the coordinate y of the organic light-emitting device 100 prepared from the organic compound provided in the embodiments of the present application is closer to 0.08.

[0268] The organic compound provided in the embodiments of the present application has a bis-phthalimide structure. By connecting the para-position of the nitrogen atom, the conjugation length and electron distribution of the molecule are effectively adjusted, which helps to form a relatively high first singlet excited state energy level. Moreover, this structure is also conducive to constructing good coplanarity, thereby achieving a relatively high glass transition temperature; in addition, the benzene ring of phthalimide is easy to introduce various functional groups, which helps to obtain a relatively low refractive index; when the film layer formed by the organic compound is combined with a high-refractive-index film layer to form a covering layer and applied to an organic light-emitting device, the luminous efficiency and color purity of the organic light-emitting device can be significantly improved.

[0269] In addition, the embodiments of the present application also provide a display panel, and the display panel includes the organic light-emitting device described in the above embodiments.

[0270] 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, "a plurality" means two or more unless otherwise specifically defined.

[0271] In the above embodiments, the descriptions of the respective embodiments have their own emphases. For the parts not detailed in a certain embodiment, reference may be made to the relevant descriptions of other embodiments.

[0272] The embodiments, implementation manners and related technical features of the present application can be combined and replaced with each other without conflict.

[0273] 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 as shown in formula (1): Wherein, L is selected from a single bond, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted fluorocycloalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylamino group having 3 to 20 carbon atoms; R1 and R2 are the same or different, and are selected from hydrogen, deuterium, halogen, nitro, cyano, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted heterocycloalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted fluorocycloalkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroarylamino group having 3 to 20 carbon atoms; n1 is selected from 0, 1, 2, 3 or 4; n2 is selected from 0, 1, 2, 3 or 4; The heteroatoms in the heteroaryl group in L and the heteroatoms in the heteroalkyl group are selected from at least one of nitrogen atom, oxygen atom, sulfur atom, phosphorus atom and silicon atom, the heteroatoms in the heteroaryl group in R1 and the heteroatoms in the heteroalkyl group are selected from at least one of nitrogen atom, oxygen atom, sulfur atom, phosphorus atom and silicon atom, and the heteroatoms in the heteroaryl group in R2 and the heteroatoms in the heteroalkyl group are selected from at least one of nitrogen atom, oxygen atom, sulfur atom, phosphorus atom and silicon atom; The expression of "—" crossing the ring structure indicates that the connection site is at any bonding position on the ring structure.

2. The organic compound according to claim 1, characterized in that, L is selected from a single bond or any one of the following structures: Wherein, n3 is selected from 0, 1, 2, 3, 4 or 5; n4 is selected from 0, 1, 2, 3 or 4; n5 is selected from 0, 1, 2, 3 or 4; n6 is selected from 0, 1, 2, 3 or 4; n7 is selected from 0, 1, 2, 3 or 4; n8 is selected from 0, 1, 2, 3 or 4; n9 is selected from 0, 1, 2, 3 or 4; n 10 selected from 0, 1, 2, 3, 4, 5 or 6; n 11 selected from 0, 1, 2, 3, 4 or 5; n 12 selected from 0, 1, 2, 3, 4 or 5; n 13 selected from 0, 1, 2, 3, 4 or 5; n 14 selected from 0, 1, 2, 3, 4 or 5; n 15 selected from 0, 1, 2, 3 or 4; The expression of "—" crossing the ring structure indicates that the connection site is at any bonding position on the ring structure; "*" indicates the connection site.

3. The organic compound according to claim 1, wherein R1 and R2 are the same or different and are selected from hydrogen, protium, deuterium, tritium, halogen, nitro, cyano, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, fluoromethyl, fluoromethoxy, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, adamantyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted diphenylamino, substituted or unsubstituted terphenyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted benzo[a]phenanthryl, substituted or unsubstituted pyridinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted furyl, substituted or unsubstituted naphtho[2,3-b]furan-2-ylphenyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyridazinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted N-phenylcarbazolyl, substituted or unsubstituted N-biphenylcarbazolyl, substituted or unsubstituted N-naphthylcarbazolyl, substituted or unsubstituted N-dibenzofuranylcarbazolyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted isoquinolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted cinnolinyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted naphthofuranyl, substituted or unsubstituted naphthothiophenyl, at least one of which; The substituent in the substituted or unsubstituted of R1 and R2 is selected from hydrogen, deuterium, halogen, cyano, nitro, trifluoromethyl, trifluoromethoxy, difluoromethyl, difluoromethoxy, fluoromethyl, fluoromethoxy, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, tert-butoxy, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, trifluoromethylbenzene, bis(trifluoromethyl)benzene, trifluoromethylbiphenyl, bis(trifluoromethyl)biphenyl, naphthyl, biphenyl, pyridinyl, at least one of which.

4. The organic compound according to claim 1 or 3, characterized in that, R1 and R2 are the same or different and are selected from deuterium, fluorine, cyano, nitro, methyl, cyclohexyl, trifluoromethyl, phenyl substituted with at least one trifluoromethyl, phenyl substituted with at least one fluorine, diphenylamino substituted with at least one trifluoromethyl, dibenzofuranyl, N-phenyl-3-dibenzofuranylamino or tetrahydropyranyl.

5. The organic compound according to claim 1, wherein The organic compound is selected from any one of the following compounds:

6. 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 a side of the organic functional layer away from the first electrode; A cover layer disposed on a side of the second electrode away from the organic functional layer; Wherein, the material of the cover layer includes at least one organic compound as described in any one of claims 1 to 5.

7. The organic light-emitting device according to claim 6, characterized in that, The covering layer includes a first sub-layer and a second sub-layer which are stacked, the first sub-layer is located 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.

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

9. The organic light emitting device according to claim 7, 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; 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; 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 according to any one of claims 6 to 9.

Images