An organic compound and use thereof

Abstract

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

Description

Technical Field

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

[0002] Organic electroluminescent devices, as an important type of electroluminescent device, have attracted the attention of many researchers due to their advantages such as active light emission without the need for a backlight, high luminous efficiency, wide viewing angle, fast response speed, wide temperature adaptability, low energy consumption, lighter and thinner design, flexible display, and huge application prospects.

[0003] Organic electroluminescent devices typically have the following structure: an anode, a cathode, and an organic material layer between them. To improve the efficiency and stability of organic EL devices, the organic material layer is composed of different functional layers, such as a hole injection layer (HIL), a hole transport layer (HTL), a light-emitting auxiliary layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer (ETL), and an electron injection layer (EIL).

[0004] An auxiliary light-emitting layer is typically positioned between the hole transport layer and the light-emitting layer. This allows holes transferred from the anode to smoothly move to the light-emitting layer, reducing the potential barrier between them, lowering the driving voltage of organic light-emitting devices (OLEDs), and blocking electrons transferred from the cathode, thus confining them within the light-emitting layer. This helps regulate the electron-hole balance within the device, improving luminous efficiency, lifetime, and stability. However, there are currently few functional materials capable of forming auxiliary light-emitting layers, especially since improvements in lifetime and luminous efficiency in OLEDs are not significant. Therefore, developing higher-performance organic functional materials to meet the requirements of panel manufacturers is crucial.

[0005] Research on organic electroluminescent materials has been widely carried out in academia and industry. However, stable and efficient organic layer materials for organic electrical components have not yet been fully developed, and the industrialization process of this technology still faces many key problems. Therefore, how to develop a light-emitting auxiliary material with high luminous efficiency, long lifespan, and improved driving voltage has always been a problem that needs to be solved by those skilled in the art. Summary of the Invention

[0006] To address the shortcomings of existing technologies, the present invention aims to provide an organic compound and its applications, specifically an organic compound, an OLED display panel, and an electronic device.

[0007] To achieve this objective, the present invention adopts the following technical solution:

[0008] In a first aspect, the present invention provides an organic compound having the structure shown in formula (I):

[0009]

[0010] Among them, L1, L2, and L3 are each independently selected from any one of single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, and substituted or unsubstituted naphthylene;

[0011] X1 and X2 are each independently selected from any one of the following groups: Among them, Y1, Y2, and Y3 are each independently selected from S, O, and NR. n or An asterisk indicates a connection point;

[0012] R n R x R y Each is independently selected from any one of the following: alkyl (C1-C10), alkenyl (C2-C10), alkoxy (C1-C6), and aryl (C6-C30);

[0013] X3 is selected from any one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted fluorenyl.

[0014] The substituents are selected from any one of C1-C10 alkyl, C2-C10 alkenyl, C1-C6 alkoxy, and C6-C30 aryl.

[0015] In a second aspect, the present invention provides an OLED display panel, the OLED display panel comprising a first electrode, a second electrode, and an organic thin film layer disposed between the first electrode and the second electrode; the organic thin film layer comprising a light-emitting auxiliary layer; the material of the light-emitting auxiliary layer comprising any one or a combination of at least two of the organic compounds described in the first aspect.

[0016] Thirdly, the present invention provides an electronic device, the electronic device comprising the OLED display panel described in the second aspect.

[0017] Compared with the prior art, the present invention has at least the following beneficial effects:

[0018] The organic compound provided by this invention possesses suitable LUMO and HOMO values, which can effectively enhance hole transport capability and effectively block electron transitions. It also has a high triplet energy level ET, which can effectively block exciton transport, confining excitons within the emissive layer and enhancing hole transport. Furthermore, the organic compound provides a rigid planar structure by introducing macrocyclic and ortho-position groups to reduce molecular symmetry, while simultaneously increasing molecular weight. This makes the material less prone to crystallization and aggregation, resulting in high photothermal stability. The energy levels of the molecule are adjusted by the electronegativity of the polar atoms O / S in the macrocyclic ring, making them more compatible with the energy levels of the hole transport layer and the emissive layer, thus improving device luminous efficiency and lifetime while reducing driving voltage. The organic compound provided by this invention can be used as a Prime material (emissive auxiliary layer material), hole transport layer material, or electron blocking layer material for OLED devices. Attached Figure Description

[0019] Figure 1 This is a schematic diagram of an OLED display panel provided in one device embodiment of the present invention;

[0020] Among them, 1-glass substrate, 2-indium tin oxide (ITO) anode, 3-first hole transport layer, 4-second hole transport layer, 5-light-emitting auxiliary layer, 6-light-emitting layer, 7-first electron transport layer, 8-second electron transport layer, 9-cathode, 10-capping layer. Detailed Implementation

[0021] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0022] In a first aspect, the present invention provides an organic compound having the structure shown in formula (I):

[0023]

[0024] Among them, L1, L2, and L3 are each independently selected from any one of single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, and substituted or unsubstituted naphthylene;

[0025] X1 and X2 are each independently selected from any one of the following groups: Among them, Y1, Y2, and Y3 are each independently selected from S, O, and NR. n or An asterisk indicates a connection point;

[0026] R n R x R yEach of the following is independently selected from any one of the following: alkyl groups of C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10), alkenyl groups of C2-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10), alkoxy groups of C1-C6 (e.g., C1, C2, C3, C4, C5, C6), and aryl groups of C6-C30 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, etc.);

[0027] X3 is selected from any one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted fluorenyl.

[0028] The substituents are selected from any one of the following: alkyl groups of C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10); alkenyl groups of C2-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10); alkoxy groups of C1-C6 (e.g., C1, C2, C3, C4, C5, C6); and aryl groups of C6-C30 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, etc.). In this invention, the term "substituent" is explained as follows: when the "substituted or unsubstituted" group is a substituted group, the substituent on the group is the "substituent." The range of substituent types is as described above, and the same expression applies below. For example, when the X3 group is selected from an alkyl-substituted phenyl group, the alkyl group on the phenyl group is the "substituent."

[0029] The organic compound provided by this invention possesses suitable LUMO and HOMO values, which can effectively enhance hole transport capability and effectively block electron transitions. It also has a high triplet energy level ET, which can effectively block exciton transport, confining excitons within the emissive layer and enhancing hole transport. Furthermore, the organic compound provides a rigid planar structure by introducing macrocyclic and ortho-position groups to reduce molecular symmetry, while simultaneously increasing molecular weight. This makes the material less prone to crystallization and aggregation, resulting in high photothermal stability. The energy levels of the molecule are adjusted by the electronegativity of the polar atoms O / S in the macrocyclic ring, making them more compatible with the energy levels of the hole transport layer and the emissive layer, thus improving device luminous efficiency and lifetime while reducing driving voltage. The organic compound provided by this invention can be used as a Prime material (emissive auxiliary layer material), hole transport layer material, or electron blocking layer material for OLED devices.

[0030] The organic compounds provided by this invention have a triarylamine-like structure at their center, which has a low number of ionic chemical sites, good electron-donating ability, and high hole mobility. The macrocyclic structure can adjust the degree of conjugation of the molecule, change the spatial configuration of the molecule, and fine-tune the energy level of the molecule by the electronegativity of the polar atoms O / S. The ortho-structures such as benzene / biphenyl are mainly used to reduce the symmetry of the molecule, enhance the rigidity of the compound, make it less prone to crystallization and aggregation between molecules, and improve the stability and film-forming properties of the material.

[0031] In one embodiment, L1, L2, and L3 are each independently selected from single bonds or phenylene oxides.

[0032] In this invention, L1, L2, and L3 preferably have the above-described structures, which can reduce the symmetry of molecules, enhance the rigidity of the compound, make it less prone to crystallization and aggregation between molecules, and improve the stability and film-forming properties of the material.

[0033] In one implementation, Y1 and Y2 are simultaneously selected from S, simultaneously selected from O, and simultaneously selected from NR. n Or selected from at the same time R n R x R y The value of is the same as that mentioned above.

[0034] In one implementation, R n R x R y Each is independently selected from alkyl groups of C1-C10 or aryl groups of C6-C30.

[0035] In one implementation, R n R x R y Each is independently selected from any one of methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, biphenyl, or naphthyl.

[0036] In this invention, R n R x R y The preferred structure can adjust the molecular configuration, increase molecular stereochemistry, and prevent molecular crystallization and aggregation.

[0037] In one embodiment, X1 and X2 are each independently selected from any one of the following groups:

[0038]

[0039] In this context, the asterisk (*) indicates a connection point.

[0040] In this invention, X1 and X2 preferably have the above-described structures. The macrocyclic structure can adjust the degree of conjugation of the molecule, change the spatial configuration of the molecule, and fine-tune the energy level of the molecule by the electronegativity of the polar atoms O / S.

[0041] In one implementation, X1 and X2 have the same value.

[0042] In one embodiment, X3 is selected from any one of the following groups:

[0043]

[0044] R1, R2, and R3 are each independently selected from any one of the following: hydrogen, deuterium, deuterated or undeuterated C1-C10 (e.g., C1, C2, C3, C4, C5, C6, C7, C8, C9, C10) alkyl, C2-C10 (e.g., C2, C3, C4, C5, C6, C7, C8, C9, C10) alkenyl, C1-C6 (e.g., C1, C2, C3, C4, C5, C6), and C6-C30 (e.g., C6, C8, C10, C12, C14, C16, C18, C20, C22, C24, C26, C28, C30, etc.); the asterisk indicates the linking site.

[0045] In one embodiment, R1, R2, and R3 are each independently selected from any one of hydrogen, deuterium, methyl, deuterated methyl, phenyl, biphenyl, and naphthyl.

[0046] In one embodiment, X3 is selected from any one of the following groups:

[0047]

[0048] In this context, the asterisk represents the connection site, and D represents deuterium.

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

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056] Where D represents deuterium.

[0057] In a second aspect, the present invention provides an OLED display panel, the OLED display panel comprising a first electrode, a second electrode, and an organic thin film layer disposed between the first electrode and the second electrode; the organic thin film layer comprising a light-emitting auxiliary layer; the material of the light-emitting auxiliary layer comprising any one or a combination of at least two of the organic compounds described in the first aspect.

[0058] In one embodiment, the organic thin film layer further includes an electron blocking layer (EBL), the material of which comprises any one or a combination of at least two of the organic compounds described in the first aspect.

[0059] In one embodiment, the organic thin film layer further includes a hole transport layer (HTL), the material of which includes any one or a combination of at least two of the organic compounds described in the first aspect.

[0060] In one embodiment, the OLED display panel further includes any one or a combination of at least two of the following: a hole injection layer (HIL), a hole blocking layer (HBL), an emissive layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL).

[0061] In the OLED display panel provided by this invention, the first electrode (anode) material can be selected from metals, such as copper, gold, silver, iron, chromium, nickel, manganese, palladium, platinum, and their alloys. The first electrode material can also be selected from metal oxides, such as indium oxide, zinc oxide, indium tin oxide (ITO), indium zinc oxide (IZO), etc. The first electrode material can also be selected from conductive polymers, such as polyaniline, polypyrrole, poly(3-methylthiophene), etc. Furthermore, the first electrode material can also be selected from materials and combinations thereof that facilitate hole injection, in addition to the first electrode materials listed above, including known materials suitable for use as the first electrode.

[0062] In the OLED display panel provided by this invention, the second electrode (cathode) material can be selected from metals, such as aluminum, magnesium, silver, indium, tin, titanium, and their alloys. The second electrode material can also be selected from multilayer metal materials, such as LiF / Al, LiO2 / Al, BaF2 / Al, etc. Besides the second electrode materials listed above, the second electrode material can also be materials and combinations thereof that facilitate electron injection, including known materials suitable for use as a second electrode.

[0063] The substrate for OLED display panels can be a rigid substrate, such as borosilicate glass, float soda-lime glass, high refractive index glass, stainless steel, etc., or a flexible substrate, such as polyimide (PI) plastic substrate, polyethylene terephthalate (PET) plastic substrate, polyethylene naphthalate (PEN) plastic substrate, polyethersulfone resin substrate (PES), polycarbonate plastic substrate (PC), ultrathin flexible glass substrate, metal foil substrate, etc.

[0064] In the OLED display panel provided by this invention, the hole injection material can be selected from any one or a combination of at least two of the following: metalloporphyrin, oligothiophene, aryl amine organic compounds, hexanitrile hexaazabenzophenanthrene organic compounds, quinacridone organic compounds, perylene organic compounds, anthraquinone, and conductive polymers based on polyaniline and polythiophene. The hole transport material can be selected from any one or a combination of at least two of the following: aryl amine organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions. The hole blocking material can be selected from 2,8-bis(diphenylphosphineoxy)dibenzothiophene, TSPO1, TPBi, 2,8-bis(diphenylphosphineoxy)dibenzofuran, and bis(2-diphenylphosphineoxy)dibenzothiophene. Diphenyl ether, lithium fluoride, 4,6-bis(3,5-di(3-pyridyl)phenyl)-2-methylpyrimidine, 4,7-diphenyl-1,10-phenanthroline, 1,3,5-tris[(3-pyridyl)-3-phenyl]benzene, tris[2,4,6-trimethyl-3-(3-pyridyl)phenyl]borane, 1,3-bis(3,5-dipyridyl-3-ylphenyl)benzene, 1,3-bis[3,5- [Di(pyridin-3-yl)phenyl]benzene, 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine, diphenylbis[4-(pyridin-3-yl)phenyl]silane, cesium carbonate, bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum, 8-hydroxyquinoline-lithium, tris(8-hydroxyquinoline)aluminum, etc., or combinations of at least two of the following:

[0065] In the OLED display panel provided by this invention, the luminescent material includes a host material and a dopant material. The host material can be selected from any one or a combination of at least two of the following: anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, organic free radical compounds, and hydroxyflavonoid-metal complexes. The dopant material can be selected from any one or a combination of at least two of the following: aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, the aromatic amine derivatives are aromatic fused-ring derivatives having substituted or unsubstituted aryl amino groups, such as pyrene, anthracene, and diindronepyrene. Furthermore, as metal complexes, iridium complexes and platinum complexes are examples.

[0066] In the OLED display panel provided by this invention, the electron transport material can be selected from any one or at least a combination of two of the following: 8-hydroxyquinoline aluminum complex (Alq3), carbazole compounds, diluted styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzoazole, benzothiazole and benzimidazole compounds; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, fluorene, etc.; and the electron injection material can be selected from any one or at least a combination of two of the following: fluorenone, anthraquinone dimethane, biphenylquinone, thiamethane dioxide, azole, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenemethane, anthrone, etc. and their derivatives, metal coordination compounds and nitrogen-containing five-membered ring derivatives.

[0067] In this embodiment of the invention, the manufacturing process of the OLED display panel is as follows: an anode (first electrode) is formed on a smooth, transparent or opaque substrate; an organic thin layer is formed on the anode; and a cathode (second electrode) is formed on the organic thin layer. The organic thin layer can be formed using known film-forming methods such as vapor deposition, sputtering, spin coating, immersion, and ion plating.

[0068] Thirdly, the present invention provides an electronic device, the electronic device comprising the OLED display panel described in the second aspect.

[0069] In one embodiment, the electronic device may be a mobile phone, computer, LCD TV, smartwatch, smart car, VR or AR headset, etc.

[0070] This invention provides several exemplary methods for preparing organic compounds with the structure of formula (1). In the following examples, the synthesis of organic compounds is described exemplary.

[0071] Synthesis of Example 1H1

[0072]

[0073] The preparation method is as follows:

[0074] Under nitrogen protection, reactants H1-1 (30 mmol) and Al (60 mmol) were completely dissolved in xylene in a round-bottom flask. Potassium carbonate (80 mmol), Pd2(dba)3 catalyst (0.5 mmol), and tri-tert-butylphosphine (0.35 mmol) were added. The mixture was then heated to 135 °C and stirred for 12 hours. The mixture was filtered hot using diatomaceous earth. After cooling the filtrate to room temperature, water was added to wash the filtrate. The organic phase was separated, and the aqueous phase was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, and compound H1 was purified by column chromatography.

[0075] MALDI-TOF: m / z: calculated value: C 46 H 27 O4N: 657.19, measured value: 657.54.

[0076] Elemental analysis results of the compound: Calculated value: C 46 H 27 O4N (%): C, 84.00; H, 4.14; O, 9.73; N, 2.13; Test value: C, 84.02; H, 4.13; O, 9.72; N, 2.14.

[0077] Example 2: Synthesis of H24

[0078]

[0079] The synthesis method of H24 is similar to that of H1, except that H1-1 and A1 in the reaction are replaced with equal amounts of H24-1 and A24, respectively.

[0080] MALDI-TOF: m / z: calculated value: C 40 H 23 NS4: 645.07, Measured value: 645.33

[0081] Elemental analysis results of the compound: Calculated value: C 40 H 23 NS4 (%): C, 74.39; H, 3.59; N, 2.17; S, 19.86; Test value: C, 74.37; H, 3.58; N, 2.18; S, 19.87.

[0082] Synthesis of Example 3H47

[0083]

[0084] The synthesis method of H47 is similar to that of H1, except that H1-1 and A1 in the reaction are replaced with equal amounts of H47-1 and A47, respectively.

[0085] MALDI-TOF: m / z: calculated value: C 50 H 31 O2N: 677.24, Measured value: 677.60

[0086] Elemental analysis results of the compound: Calculated value: C 50 H 31 O2N (%): C, 88.60; H, 4.61; O, 4.72; N, 2.07; Test value: C, 88.63; H, 4.60; O, 4.71; N, 2.06.

[0087] Synthesis of H65 in Example 4

[0088]

[0089] The synthesis method of H65 is similar to that of H1, except that H1-1 and A1 in the reaction are replaced with equal amounts of H65-1 and A65, respectively.

[0090] MALDI-TOF: m / z: calculated value: C 40 H 27 O2N: 553.20, Measured value: 553.56

[0091] Elemental analysis results of the compound: Calculated value: C 40 H 27 O2N (%): C, 86.78; H, 4.92; O, 5.78; N, 2.53; Test value: C, 86.80; H, 4.91; O, 5.77; N, 2.52.

[0092] Synthesis of Example 5H71

[0093]

[0094] The synthesis method of H71 is similar to that of H1, except that H1-1 and A1 in the reaction are replaced with equal amounts of H71-1 and A71, respectively.

[0095] MALDI-TOF: m / z: calculated value: C 50 H 39 N5: 709.32, Measured value: 709.63

[0096] Elemental analysis results of the compound: Calculated value: C 50 H 39N5 (%): C, 84.60; H, 5.54; N, 9.87; Test value: C, 84.63; H, 5.52; N, 9.86.

[0097] Synthesis of Example 6H78

[0098]

[0099] The synthesis method of H78 is similar to that of H1, except that H1-1 and A1 in the reaction are replaced with equal amounts of H78-1 and A78, respectively.

[0100] MALDI-TOF: m / z: calculated value: C 60 H 43 N5: 833.35, Measured value: 833.76

[0101] Elemental analysis results of the compound: Calculated value: C 60 H 43 N5 (%): C, 86.41; H, 5.20; N, 8.40; Test value: C, 86.43; H, 5.18; N, 8.39.

[0102] Synthesis of H82 in Example 7

[0103]

[0104] The synthesis method of H82 is similar to that of H1, except that H1-1 and A1 in the reaction are replaced with equal amounts of H82-1 and A82, respectively.

[0105] MALDI-TOF: m / z: calculated value: C 58 H 51 N: 761.40, Measured value: 761.85

[0106] Elemental analysis results of the compound: Calculated value: C 58 H 51 N (%): C, 91.42; H, 6.75; N, 1.84; Test value: C, 91.40; H, 6.76; N, 1.84.

[0107] Synthesis of Example 8H95

[0108]

[0109] The synthesis method of H95 is similar to that of H1, except that H1-1 and A1 in the reaction are replaced with equal amounts of H95-1 and A95, respectively.

[0110] MALDI-TOF: m / z: calculated value: C 52 H47 N: 685.37, Measured value: 685.37

[0111] Elemental analysis results of the compound: Calculated value: C 52 H 47 N (%): C, 91.05; H, 6.91; N, 2.04; Test value: C, 91.02; H, 6.92; N, 2.05.

[0112] Synthesis of Example 9H98

[0113]

[0114] The synthesis method of H98 is similar to that of H1, except that H1-1 and A1 in the reaction are replaced with equal amounts of H98-1 and A98, respectively.

[0115] MALDI-TOF: m / z: calculated value: C 61 H 56 N: 802.44, Measured value: 802.86

[0116] Elemental analysis results of the compound: Calculated value: C 61 H 56 N (%): C, 91.23; H, 7.03; N, 1.74; Test value: C, 91.20; H, 7.05; N, 1.76.

[0117] Synthesis of Example 10H101

[0118]

[0119] The synthesis method of H101 is similar to that of H1, except that H1-1 and A1 in the reaction are replaced with equal amounts of H101-1 and A101, respectively.

[0120] MALDI-TOF: m / z: calculated value: C 40 H 21 D6O2N: 559.24, measured value: 559.42

[0121] Elemental analysis results of the compound: Calculated value: C 40 H 21 D6O2N (%): C, 85.84; H, 5.94; O, 5.72; N, 2.50; ; Test value: C, 85.85; H, 5.93; O, 5.72; N, 2.50.

[0122] Synthesis of H1O3 in Example 11

[0123]

[0124] The synthesis method of H103 is similar to that of H1, except that H1-1 and A1 in the reaction are replaced with equal amounts of H103-1 and A103, respectively.

[0125] MALDI-TOF: m / z: calculated value: C 40 H 20 D7O2N: 560.25, Measured value: 560.36

[0126] Elemental analysis results of the compound: Calculated value: C 40 H 20 D7O2N (%): C, 85.69; H, 6.11; O, 5.71; N, 2.50; Test value: C, 85.70; H, 6.10; O, 5.70; N, 2.50.

[0127] Device Example 1

[0128] This embodiment of the device provides an OLED display panel, the structural schematic of which is shown below. Figure 1 As shown, the OLED display panel includes a glass substrate 1, an indium tin oxide (ITO) anode 2, a first hole transport layer 3, a second hole transport layer 4, a light-emitting auxiliary layer 5, a light-emitting layer 6, a first electron transport layer 7, a second electron transport layer 8, a cathode 9, and a capping layer 10, stacked sequentially. The ITO anode 2 has a thickness of 15 nm, the first hole transport layer 3 has a thickness of 10 nm, the second hole transport layer 4 has a thickness of 100 nm, the light-emitting auxiliary layer 5 has a thickness of 90 nm, the light-emitting layer 6 has a thickness of 40 nm, the first electron transport layer 7 has a thickness of 35 nm, the second electron transport layer 8 has a thickness of 5 nm, the cathode 9 has a thickness of 14 nm (magnesium-silver electrode, magnesium-silver mass ratio 1:9), and the capping layer (CPL) 10 has a thickness of 70 nm.

[0129] The manufacturing steps of an OLED display panel are as follows:

[0130] (1) Cut the glass substrate 1 into 50mm×50mm×0.7mm pieces, sonicate them in isopropanol and deionized water for 30min respectively, then wash them repeatedly with distilled water twice, and then expose them to ozone for 10min for cleaning; mount the glass substrate with ITO anode 2 obtained by magnetron sputtering onto the vacuum deposition equipment.

[0131] (2) At a vacuum degree of 2×10 -6 At Pa, HAT-CN compound with a thickness of 10 nm was vacuum deposited on the ITO anode layer 2 at a deposition rate of 0.5 A / s to serve as the first hole transport layer 3.

[0132] (3) At a evaporation rate of 1A / s, the compound TAPC was vacuum-deposited on the first hole transport layer 3 as the second hole transport layer 4 with a thickness of 100nm.

[0133] (4) The compound H1 of the present invention is vacuum-deposited as a light-emitting auxiliary layer 5 with a thickness of 90 nm on the second hole transport layer 4 at a deposition rate of 1 A / s.

[0134] (5) Vacuum evaporation layer 6 is deposited on the light-emitting auxiliary layer 5 at a evaporation rate of 1A / s. The light-emitting layer is composed of a host and a dopant, wherein HOST X is the host material and Ir(piq)2(acac) is the dopant material. The mass ratio of the host material to Ir(piq)2(acac) is 95:5 and the thickness is 40nm.

[0135] (5) The compound BCP was vacuum-deposited on the light-emitting layer 6 at a deposition rate of 1A / s as the first electron transport layer 7 with a thickness of 35nm.

[0136] (6) The compound Alq3 was vacuum-deposited on the first electron transport layer 7 at a deposition rate of 0.5 A / s as the second electron transport layer 8 with a thickness of 5 nm.

[0137] (7) A magnesium-silver electrode is vacuum-deposited as a cathode 9 on the second electron transport layer 8 at a deposition rate of 1A / s, with a Mg to Ag mass ratio of 1:9 and a thickness of 14nm.

[0138] (8) A high-refractive-index compound CBP is vacuum-deposited on the cathode 9 at a deposition rate of 1A / s, with a thickness of 70nm, and used as a cathode capping layer (capping layer) 10.

[0139] The compound structure used in the OLED device is as follows:

[0140]

[0141] Device Examples 2-11

[0142] In device example 1, the organic compound H1 in step (4) is replaced with equal amounts of compounds H24, H47, H65, H71, H78, H82, H95, H98, H101 or H103, and the other preparation steps are the same as in device example 1.

[0143] Device Comparison Example 1

[0144] An OLED display panel, which differs from device embodiment 1 only in that the optical auxiliary layer material H1 in step (4) is replaced with an equal amount of the comparative compound HH. Replacement; other raw materials and preparation steps are the same.

[0145] Performance evaluation of OLED display panels:

[0146] The current of the OLED device (i.e., the OLED display panel provided in the device embodiments and device comparative examples of this invention) under different voltages was measured using a Keithley 2365A digital nanovoltmeter. The current density of the OLED device under different voltages was then obtained by dividing the current by the luminescent area. The brightness and radiant energy flux density of the OLED device under different voltages were measured using a Konicaminolta CS-2000 spectroradiometer. Based on the current density and brightness of the OLED device under different voltages, the current density (10 mA / cm²) at the same voltage was obtained. 2 The operating start-up voltage and current efficiency CE (Cd / A), where Von is the luminance per 1 Cd / m². 2 The start-up voltage was measured; the lifetime LT95 was obtained by measuring the time it took for the OLED device to reach 95% of its initial brightness; the voltage / efficiency / lifetime of compound HH was compared with the performance of other device structures at 100%, and the data are shown in Table 1.

[0147] Table 1 OLED Device Performance Test Results

[0148]

[0149]

[0150] As shown in Table 1, compared with the comparative compounds, the organic light-emitting devices prepared based on the light-emitting auxiliary layer material of this application exhibit lower driving voltage (Von is 96.4%-97.7% of the comparative devices), higher current efficiency (CE is 102.4%-104.4% of the comparative devices), and longer device lifetime (LT95 is 106.5%-117.8% of the comparative devices).

[0151] The compound skeleton of this invention is similar to that of the comparative compounds, but the degree of functional group conjugation, the connection mode of functional groups, and the spatial stereochemistry are different. Devices based on the compounds of this invention allow holes transferred from the anode to move more smoothly to the light-emitting layer, acting as a step in the energy level. This reduces the potential barrier between the hole transport layer and the light-emitting layer, lowers the driving voltage of the organic electroluminescent device, further increases hole utilization, and thus improves the device's lifetime. Device performance results show that the organic compounds of this application are more suitable as light-emitting auxiliary layer materials compared to the comparative compounds. Moreover, the enhanced stereochemistry of the molecular structure of the organic compounds of this application can also reduce intermolecular forces and decrease intermolecular stacking, resulting in better device stability. By introducing various substituents into the core structure, the energy levels can be fine-tuned, and the interfacial properties between organic materials can be adjusted, thereby broadening the application range of the material.

[0152] The applicant declares that the above embodiments illustrate the organic compounds and their applications, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of the raw materials used in the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. An organic compound, characterized in that, The organic compound has the structure shown in formula (I): Formula (I) Among them, L1, L2, and L3 are each independently selected from single bonds or phenylene; X1 and X2 are each independently selected from any one of the following groups: The asterisk (*) indicates a connection point. X3 is selected from any one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted fluorenyl. The substituents are selected from any one of C1-C10 alkyl, C2-C10 alkenyl, C1-C6 alkoxy, and C6-C30 aryl.

2. The organic compound according to claim 1, characterized in that, X1 and X2 have the same value.

3. The organic compound according to claim 1, characterized in that, X3 is selected from any one of the following groups: R1, R2, and R3 are each independently selected from any one of hydrogen, deuterium, deuterated or undeuterated C1-C10 alkyl, C2-C10 alkenyl, C1-C6 alkoxy, and C6-C30 aryl; the asterisk indicates the linking site.

4. The organic compound according to claim 3, characterized in that, R1, R2, and R3 are each independently selected from any one of hydrogen, deuterium, methyl, deuterated methyl, phenyl, biphenyl, and naphthyl.

5. The organic compound according to claim 1, characterized in that, X3 is selected from any one of the following groups: In this context, the asterisk represents the connection site, and D represents deuterium.

6. The organic compound according to claim 1, characterized in that, The organic compound is selected from any one of the following compounds: 。 7. An OLED display panel, characterized in that, The OLED display panel includes a first electrode, a second electrode, and an organic thin film layer disposed between the first electrode and the second electrode; The organic thin film layer includes a light-emitting auxiliary layer; The material of the light-emitting auxiliary layer includes any one or a combination of at least two of the organic compounds described in any one of claims 1-6.

8. The OLED display panel according to claim 7, characterized in that, The organic thin film layer further includes an electron blocking layer, the material of which comprises any one or a combination of at least two of the organic compounds described in any one of claims 1-6.

9. The OLED display panel according to claim 7, characterized in that, The organic thin film layer further includes a hole transport layer, the material of which includes any one or a combination of at least two of the organic compounds described in any one of claims 1-6.

10. An electronic device, characterized in that, The electronic device includes the OLED display panel as described in claim 7.

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