Organic compound and display panel

Abstract

An organic compound and a display panel. The organic compound has a structure as shown in general formula (1): general formula (1).

Description

Organic compounds and display panels

[0001] This application claims priority to Chinese patent application No. 202410370420.2 filed on March 28, 2024, the entire contents of which are incorporated herein by reference. Technical Field

[0002] The present application belongs to the field of display technology, and specifically relates to an organic compound and a display panel. Background Art

[0003] Organic electroluminescent elements typically have an anode, a cathode, and an organic layer located between them. They utilize the organic materials in the organic layer to convert electrical energy into light energy, thereby achieving organic electroluminescence. When a voltage is applied between the anode and cathode of an organic electroluminescent element, the anode injects holes into the organic layer, while the cathode injects electrons into the organic layer. The injected holes and electrons interact to form excitons, which then emit light when they transition back to their ground state, thereby achieving luminescence in the organic electroluminescent element. Organic electroluminescent elements offer advantages such as autonomous luminescence, high brightness, high efficiency, low-voltage drive, wide viewing angle, high contrast, and high response. Therefore, organic electroluminescent devices have broad application prospects. With the increasing demand for display effects in recent years, the development of high-color gamut display devices has become a focus of attention. Among these, the development of materials that can achieve higher luminous efficiency and higher color purity in organic electroluminescent elements to meet the needs of high-color gamut display devices is a key area of ​​focus. Currently, In order to improve the color purity, lifespan and luminous efficiency of organic electroluminescent elements, thereby obtaining display panels with better display performance, the materials used in the organic layers (such as the light-emitting layer) of the organic electroluminescent elements still need to be improved.

[0004] Therefore, an organic compound and a display panel are urgently needed to solve the above technical problems. Technical issues

[0005] An embodiment of the present application provides an organic compound and a display panel. By providing an organic compound with a multiple resonance effect, the organic compound adopts a nitrogen-containing fused ring as the core structure, and by introducing nitrogen atoms to adjust the triplet energy level and multiple resonance effect of the organic compound molecule, the material properties of the organic compound are improved, thereby improving the luminous efficiency of the display panel using the organic compound and extending the service life. Technical Solutions

[0006] In a first aspect, the present application provides an organic compound having a structure as shown in general formula (1):

[0007] wherein X1 is selected from C or N;

[0008] A1, A2, A3 and A4 are each independently selected from a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms;

[0009] R1, R2, R3 and R4, at each occurrence, are independently selected from H, D, T, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 2 to 30 carbon atoms;

[0010] m, n, p, and q are each independently selected from any integer from 0 to 11;

[0011] When m is greater than or equal to 2, adjacent R1s may form a ring or not;

[0012] When n is greater than or equal to 2, adjacent R2s may form a ring or not;

[0013] When p is greater than or equal to 2, adjacent R3 may form a ring or not;

[0014] When q is greater than or equal to 2, adjacent R4 may form a ring or may not form a ring.

[0015] In a second aspect, the present application further provides a display panel, comprising:

[0016] substrate;

[0017] A first electrode layer is provided on one side of the substrate;

[0018] a second electrode layer, disposed on a side of the first electrode layer away from the substrate;

[0019] an organic functional layer, disposed between the first electrode layer and the second electrode layer;

[0020] Wherein, the material of the organic functional layer includes at least one organic compound as mentioned above. BRIEF DESCRIPTION OF THE DRAWINGS

[0021] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the following briefly introduces the drawings required for use in the description of the embodiments. Obviously, the drawings described below are only some embodiments of the present application. For those skilled in the art, other drawings can be obtained based on these drawings without creative work.

[0022] FIG1 is a schematic structural diagram of a light-emitting element provided in an embodiment of the present application;

[0023] FIG2 is a steady-state fluorescence spectrum of organic compounds M1 to M8 provided in Examples of the present application;

[0024] FIG3 is a schematic structural diagram of a display panel provided in an embodiment of the present application. Modes for Carrying Out the Invention

[0025] The following will clearly and completely describe the technical solutions in the embodiments of this application in conjunction with the accompanying drawings. Obviously, the described embodiments are only some of the embodiments of this application, not all of the embodiments. Based on the embodiments of this application, all other embodiments obtained by those skilled in the art without inventive work are within the scope of protection of this application. In addition, it should be understood that the specific embodiments described herein are only for the purpose of illustrating and explaining this application and are not intended to limit this application. In this application, unless otherwise stated, directional words such as "upper" and "lower" generally refer to the upper and lower parts of the device in actual use or operation, specifically the directions in the drawings in the accompanying drawings; while "inner" and "outer" refer to the outline of the device. In this application, "optionally", "optional", and "optional" mean optional, that is, they can be selected from either of the two parallel options of "with" or "without". If multiple "optional" items appear in a technical solution, unless otherwise specified and there are no contradictions or mutual constraints, each "optional" item is independent. In this application, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions containing the listed features.

[0026] In this application, aryl, aromatic group, aromatic group, aromatic family, and aromatic ring system have the same meaning and can be interchanged.

[0027] In the present application, heteroaryl, heteroaromatic group, heteroaromatic group, heteroaromatic family, and heteroaromatic ring system have the same meaning and can be interchanged.

[0028] In the present application, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0029] In this application, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0030] In the present application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it is understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to: D, T, cyano, isocyano, nitro or halogen groups, alkyl groups containing 1-20 carbon atoms, heterocyclic groups containing 3-20 carbon atoms, aromatic groups containing 6-20 carbon atoms, heteroaromatic groups containing 5-20 carbon atoms, -NR'R", silanyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from but not limited to: H, D, T, cyano, isocyano, nitro or halogen, 1- Preferably, R is selected from but not limited to: deuterium atom, cyano group, isocyano group, nitro or halogen group, alkyl group containing 1-10 carbon atoms, heterocyclic group containing 3-20 carbon atoms, aromatic group containing 6-20 carbon atoms, heteroaromatic group containing 5-20 carbon atoms, silanyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups can also be further substituted by substituents acceptable in the art. Halogen group includes fluoro (-F), chloro (-Cl), bromo (-Br), iodo (-I) etc.

[0031] In the present application, "aromatic group or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, which can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted aromatic group having 6 to 40 ring atoms" refers to an aromatic group containing 6 to 40 ring atoms, preferably a substituted or unsubstituted aromatic group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted aromatic group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted aromatic group having 6 to 14 ring atoms, and the aromatic group is optionally further substituted; suitable examples include, but are not limited to, phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, perylenyl, naphthphenyl, fluorenyl, perylene, acenaphthenyl, and their derivatives. It is understood that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g. <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aromatic groups.

[0032] In the present application, "heteroaromatic group or heteroaromatic group" means that at least one carbon atom is replaced by a non-carbon atom on the basis of an aromatic group, and the non-carbon atom can be an N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" means a heteroaryl group having 5 to 40 ring atoms, preferably a substituted or unsubstituted heteroaryl group having 6 to 30 ring atoms, more preferably a substituted or unsubstituted heteroaryl group having 6 to 18 ring atoms, and particularly preferably a substituted or unsubstituted heteroaryl group having 6 to 14 ring atoms, and the heteroaryl group is optionally further substituted. Suitable examples include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidine 1-Hydroxy-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine, 1-dopamine-1-dopamine,

[0033] In this application, "alkyl" may refer to a straight chain, branched chain and / or cyclic alkyl group. The carbon number of the alkyl group may be 1 to 50, 1 to 30, 1 to 20, 1 to 10 or 1 to 6. Phrases containing this term, for example, "C 1-9"Alkyl" refers to an alkyl group containing 1 to 9 carbon atoms, which can be independently C1 alkyl, C2 alkyl, C3 alkyl, C4 alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl or C9 alkyl at each occurrence. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, 4-methylcyclohexyl, 4-tert-butylcyclohexyl, n-heptyl, 1-methylheptyl, 2,2-dimethylheptyl, 2-ethylheptyl, 2-butylheptyl, n-octyl, tert-octyl, 2-ethyloctyl, 2-butyloctyl, 2-hexyloctyl 1-Hexyl, 2 ...

[0034] In this application, "*" connected to a single bond indicates a connection or fusion site.

[0035] In the present application, when a linking site is not specified in a group, it means that any linking site in the group can be used as the linking site.

[0036] In the present application, when no fusion site is specified in a group, it means that any fusion site in the group can be used as the fusion site, and preferably two or more sites in the adjacent position in the group are fusion sites.

[0037] In this application, when a group contains multiple substituents with the same symbol, the substituents may be the same or different from each other, for example The six Rs on the benzene ring may be the same as or different from each other.

[0038] In the present application, the single bond connecting the substituent runs through the corresponding ring, indicating that the substituent can be connected to any position of the ring, for example In which R is connected to any substitutable position of the benzene ring; express Can be used with The benzene ring can be fused at any position.

[0039] The cyclic alkyl group or cycloalkyl group described in the present application have the same meaning and can be interchanged.

[0040] In the present application, "adjacent groups" refers to two substituents with no substitutable sites between them.

[0041] In the present application, "two adjacent R1 or R3 or R5 form a ring with each other" means a ring system formed by two adjacent R1 or R3 or R5 connected to each other, and the ring system can be selected from aliphatic hydrocarbon ring, aliphatic heterocycle, aromatic hydrocarbon ring or aromatic heterocycle. Preferably,

[0042] In this application, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) energy levels can be measured by photoelectric effect, such as X-ray photoelectron spectroscopy (XPS) and ultraviolet photoelectron spectroscopy (UPS) or by cyclic voltammetry (CV). In addition, quantum chemical methods, such as density functional theory (DFT), are also effective methods for calculating molecular orbital energy levels.

[0043] The luminescence lifetime of organic materials can be obtained by techniques such as time-correlated single photon counting (TCSPC).

[0044] The present application provides an organic compound with a multiple resonance effect. The organic compound uses a nitrogen-containing fused ring as the core structure. By introducing nitrogen atoms, the triplet energy level and multiple resonance effect of the organic compound molecule are adjusted, thereby improving the material properties of the organic compound, thereby improving the luminous efficiency of the display panel using the organic compound and extending the service life.

[0045] The present invention provides an organic compound having a structure as shown in the general formula (1):

[0046] wherein X1 is selected from C or N;

[0047] A1, A2, A3 and A4 are each independently selected from a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms;

[0048] R1, R2, R3 and R4, at each occurrence, are independently selected from H, D, T, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 2 to 30 carbon atoms;

[0049] m, n, p, and q are each independently selected from any integer from 0 to 11;

[0050] When m is greater than or equal to 2, adjacent R1s may form a ring or not;

[0051] When n is greater than or equal to 2, adjacent R2s may form a ring or not;

[0052] When p is greater than or equal to 2, adjacent R3 may form a ring or not;

[0053] When q is greater than or equal to 2, adjacent R4 may form a ring or may not form a ring.

[0054] The organic compound is an organic compound with a multiple resonance effect. The multiple resonance effect refers to the atomic-level positioning and separation of frontier molecular orbitals due to the special positions of electron-donating groups and electron-withdrawing groups in polycyclic aromatic hydrocarbons with special structures, which is conducive to achieving an extremely narrow emission spectrum and suppressing the intensity of the shoulder peak at long wavelengths in the emission spectrum, thereby improving the color purity of the luminescence of the organic compound; at the same time, due to the relatively fixed molecular skeleton of the multiple resonance type molecule (mostly with boron-nitrogen fused ring, boron-oxygen fused ring, or boron-sulfur fused ring as the core structure), its synthesis conditions are complex and the yield is low, the emission spectrum is difficult to adjust, and it is difficult to obtain materials that can meet commercial needs. The organic compound has a structure as shown in general formula (1), uses nitrogen-containing fused rings as the core structure, and adjusts the triplet energy level and multiple resonance effect of the organic compound molecule by introducing nitrogen atoms, which is conducive to reducing the shoulder peak in the emission spectrum of the organic compound, thereby improving the luminescence performance of the organic compound, improving the luminescence efficiency and color purity of the display panel using the organic compound, and extending the service life.

[0055] The present application provides an organic compound with a multiple resonance effect. The organic compound uses a nitrogen-containing fused ring as the core structure. By introducing nitrogen atoms, the triplet energy level and multiple resonance effect of the organic compound molecule are adjusted, thereby improving the material properties of the organic compound, thereby improving the luminous efficiency of the display panel using the organic compound and extending the service life.

[0056] In some embodiments, considering the availability of raw materials for the organic compound, when X1 is selected from N, A1 is the same as A4, and A2 is the same as A3, this facilitates obtaining more readily available raw materials and reduces production costs. Preferably, when X1 is selected from N, A1 is the same as A4, A2 is the same as A3, R1 is the same as R4, and R2 is the same as R3, so that the raw materials for the synthesis of the organic compound are readily available, the types of raw materials required for synthesis are reduced, the process is simplified, and production costs are reduced.

[0057] In some embodiments, when X1 is selected from N, A1 is the same as A4, A2 is the same as A3, R1 is the same as R4, and R2 is the same as R3, the structure of the organic compound can be as shown in formula (2):

[0058] Similarly, in some embodiments, considering the availability of raw materials for the organic compound, when X1 is selected from C, A1 is the same as A2, and A3 is the same as A4, this facilitates obtaining more readily available raw materials and reduces production costs. Preferably, when X1 is selected from C, A1 is the same as A2, A3 is the same as A4, R1 is the same as R2, and R3 is the same as R4, so that the raw materials for the synthesis of the organic compound are readily available, the types of raw materials required for synthesis are reduced, the process is simplified, and production costs are reduced.

[0059] In some embodiments, when X1 is selected from C, A1 is the same as A2, A3 is the same as A4, R1 is the same as R2, and R3 is the same as R4, the structure of the organic compound can be as shown in formula (3):

[0060] In some embodiments, A1, A2, A3, and A4 are independently selected from any one of the structures shown in (1-1) to (1-4):

[0061] wherein Z is selected from C, CR5 or N;

[0062] Y is selected from CR6R7, O or S;

[0063] R5, at each occurrence, is independently selected from H, D, T, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 2 to 30 carbon atoms, and adjacent Rs may be cyclic or acyclic;

[0064] Each occurrence of R6 and R7 is independently selected from substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, and substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms.

[0065] In some embodiments, when Z is selected from C, Z is a fusion site.

[0066] In some embodiments, when A1, A2, A3, and A4 are independently selected from any one of the structures shown in (1-1) to (1-4), A1, A2, A3, and A4 are independently selected from the following structures:

[0067] Among them, Z1 is selected from CR5.

[0068] In some embodiments, when A1, A2, A3 and A4 are independently selected from any one of the structures shown in (1-1) to (1-4), in A1, R5 and R1 have the same meaning; in A2, R5 and R2 have the same meaning; in A3, R5 and R3 have the same meaning; in A4, R5 and R4 have the same meaning.

[0069] In some embodiments, each occurrence of R1, R2, R3, R4, and R5 is independently selected from H, D, T, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 20 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 2 to 20 carbon atoms.

[0070] In some embodiments, each occurrence of R1, R2, R3, R4, and R5 is independently selected from H, D, T, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 10 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 10 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 10 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 15 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 15 carbon atoms.

[0071] In some embodiments, each occurrence of R1, R2, R3, R4, and R5 is independently selected from H, D, T, F, Cl, cyano, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted alkoxy having 1 to 5 carbon atoms, substituted or unsubstituted alkylthio having 1 to 5 carbon atoms, substituted or unsubstituted alkenyl having 2 to 5 carbon atoms, substituted or unsubstituted alkynyl having 2 to 5 carbon atoms, substituted or unsubstituted aryl having 6 to 12 carbon atoms, or substituted or unsubstituted heteroaromatic having 5 to 15 carbon atoms.

[0072] In some embodiments, each occurrence of R1, R2, R3, R4, and R5 is independently selected from H, D, T, F, Cl, cyano, methyl, ethyl, tert-butyl, n-pentyl, cyclohexyl, ethynyl, or the following:

[0073] Wherein, “*” indicates the connection site.

[0074] In some embodiments, when at least two adjacent R1s form a ring, the ring formed by at least two adjacent R1s forms a parallel ring structure with A1; when at least two adjacent R2s form a ring, the ring formed by at least two adjacent R2s forms a parallel ring structure with A2; when at least two adjacent R3s form a ring, the ring formed by at least two adjacent R3s forms a parallel ring structure with A3; when at least two adjacent R4s form a ring, the ring formed by at least two adjacent R4s forms a parallel ring structure with A4.

[0075] In some embodiments, the parallel ring structure formed by the ring formed by at least two adjacent R1s and A1, the parallel ring structure formed by the ring formed by at least two adjacent R2s and A2, the parallel ring structure formed by at least two adjacent R3s and A3, and the parallel ring structure formed by at least two adjacent R4s and A4 are independently selected from the following groups each time: substituted or unsubstituted aromatic groups having 10 to 15 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 8 to 18 carbon atoms.

[0076] In some embodiments, when A1, A2, A3, and A4 are independently selected from any one of the structures shown in (1-1) to (1-4), and at least two adjacent R5 form a ring, at least two adjacent R5 form a substituted or unsubstituted alicyclic group having 5 to 7 carbon atoms.

[0077] In some embodiments, when A1, A2, A3 and A4 are independently selected from any one of the structures shown in (1-1) to (1-4), and at least two adjacent R5 form a ring, the ring formed by at least two adjacent R5 and the adjacent A1, A2, A3 or A4 form a parallel ring structure, which can be independently selected from a substituted or unsubstituted aromatic group having 10 to 15 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 8 to 18 carbon atoms.

[0078] In some embodiments, when A1, A2, A3, and A4 are independently selected from any one of the structures shown in (1-1) to (1-4), and at least two adjacent R5s form a ring, the ring formed by at least two adjacent R5s and the adjacent A1, A2, A3, or A4 can be selected from the following structures:

[0079] In some embodiments, each occurrence of R6 and R7 is independently selected from a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms, or a substituted or unsubstituted aromatic group having 6 to 15 carbon atoms.

[0080] In some embodiments, each occurrence of R6 and R7 is independently selected from a substituted or unsubstituted alkyl group having 1 to 5 carbon atoms, or a substituted or unsubstituted aromatic group having 6 to 10 carbon atoms.

[0081] In some embodiments, each occurrence of R6 and R7 is independently selected from methyl or phenyl.

[0082] In some embodiments, m, n, p, and q are each independently selected from any integer from 0 to 11, that is, m, n, p, and q are each independently selected from any integer from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, and 11.

[0083] In some embodiments, the organic compound is selected from the following compounds:

[0084] In some embodiments, the highest occupied molecular orbital energy level of the organic compound is greater than or equal to -6.0 eV, and the highest occupied molecular orbital energy level of the organic compound is less than or equal to -5.0 eV, for example, it can be -5.9 eV, -5.8 eV, -5.7 eV, -5.6 eV, -5.5 eV, -5.4 eV, -5.3 eV, -5.2 eV, -5.1 eV, etc.

[0085] In some embodiments, the lowest unoccupied molecular orbital energy level of the organic compound is greater than or equal to -3.0 eV, and the lowest unoccupied molecular orbital energy level of the organic compound is less than or equal to -2.0 eV, for example, it can be -2.9 eV, -2.8 eV, -2.7 eV, -2.6 eV, -2.5 eV, -2.4 eV, -2.3 eV, -2.2 eV, -2.1 eV, etc.

[0086] In some embodiments, the emission spectrum of the dilute solution of the organic compound at room temperature ranges from 380 nm to 800 nm. Preferably, the emission spectrum of the dilute solution of the organic compound at room temperature ranges from 400 nm to 500 nm. The dilute solution of the organic compound can be a solution of the organic compound dissolved in a solvent such as toluene to form a solution with a concentration of 10 -4 mol / L to 10 -6 mol / L (e.g., 10 -5 mol / L) to obtain a dilute solution.

[0087] In some embodiments, the half-peak width of the emission spectrum of the dilute solution of the organic compound at room temperature is less than 60 nanometers, for example, it can be 9 nanometers, 10 nanometers, 15 nanometers, 20 nanometers, 30 nanometers, 40 nanometers, 50 nanometers, etc., which is beneficial to improving the color purity of the luminescence of the organic compound.

[0088] In some embodiments, the maximum emission peak of the emission spectrum of the dilute solution of the organic compound at room temperature is between 450 nm and 470 nm, which is conducive to obtaining a blue light-emitting material with higher color purity and a maximum emission wavelength that better meets commercial needs.

[0089] In some embodiments, the fluorescence lifetime of the solid-state thin film formed by the organic compound is between 1 microsecond and 100 milliseconds. For example, when the organic compound contains heavy atom substituents, the fluorescence lifetime of the organic compound can be effectively extended to the millisecond level.

[0090] The organic compound with a multiple resonance effect provided in the embodiment of the present application adopts a nitrogen-containing fused ring as the core structure, and adjusts the triplet energy level and multiple resonance effect of the organic compound molecule by introducing nitrogen atoms, thereby improving the material properties of the organic compound, thereby improving the luminous efficiency of the display panel using the organic compound and extending the service life.

[0091] Referring to FIG. 1 , the present application further provides a light-emitting element 100 comprising: a pair of electrodes, including a first electrode layer 101 and a second electrode layer 102; and an organic functional layer 103 positioned between the first electrode layer 101 and the second electrode layer 102. The material of the organic functional layer 103 comprises one or more of the organic compounds described above. The first electrode layer 101 may be an anode, and the second electrode layer 102 may be a cathode.

[0092] In some embodiments, the light-emitting element 100 can be used for organic light-emitting diodes, organic photovoltaic cells, organic light-emitting cells, organic field-effect transistors, organic light-emitting field-effect transistors, organic lasers, organic spintronic devices, organic sensors, and organic plasmon emitting diodes, etc., preferably organic light-emitting diodes, organic light-emitting cells, and organic light-emitting field-effect transistors.

[0093] In some embodiments, the light emitting element 100 can be applied to various electronic devices, such as display panels, lighting devices, light sources, etc.

[0094] In some embodiments, the organic functional layer 103 includes at least a light-emitting layer 107 ; preferably, the organic functional layer 103 includes a hole injection layer 104 , a hole transport layer 105 , an electron blocking layer 106 , a light-emitting layer 107 , a hole blocking layer 108 , an electron transport layer 109 and an electron injection layer 110 .

[0095] In some embodiments, the light emitting element 100 may be a blue light emitting element, a green light emitting element, or a red light emitting element.

[0096] In some embodiments, the light-emitting layer 107 may include a host material and a guest material, wherein the guest material is one or more of the organic compounds described above. When the guest material is selected from one or more of the organic compounds described above, the light-emitting element 100 is preferably a blue light-emitting element, and the light-emitting wavelength of the light-emitting element 100 is within the wavelength range of blue light.

[0097] In some embodiments, the host material includes a fused aromatic derivative or a heteroaromatic compound.

[0098] In some embodiments, the host material includes fused aromatic ring derivatives, heterocyclic compounds, etc., for example, at least one of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives.

[0099] In some embodiments, when the light-emitting layer 107 includes the host material and the guest material, the mass ratio of the host material to the guest material is 199.5:0.5 to 190:10, such as 199:1, 198:2, 195:5, 193:7, 192:8, 191:9, etc. The guest material is dispersed in the host material, and the mass ratio of the host material to the guest material is 199.5:0.5 to 190:10, which helps to suppress crystallization of the light-emitting layer 107 and concentration quenching caused by high concentration of the guest material, thereby improving the luminous efficiency of the light-emitting element 100.

[0100] In some embodiments, the light-emitting layer 107 further includes a sensitizer, which can be selected from at least one of a phosphorescent material and a TADF (Thermally Activated Delayed Fluorescence) material. The addition of the sensitizer effectively utilizes triplet excitons within the light-emitting element 100 and transfers energy to the organic compound via energy transfer, thereby improving both luminous efficiency and the stability of the light-emitting element 100.

[0101] In some embodiments, the highest occupied molecular orbital energy level of the sensitizer is greater than or equal to -6.0 eV, and the highest occupied molecular orbital energy level of the sensitizer is greater than or equal to -5.0 eV, for example, it can be -5.9 eV, -5.8 eV, -5.7 eV, -5.6 eV, -5.5 eV, -5.4 eV, -5.3 eV, -5.2 eV, -5.1 eV, etc.

[0102] In some embodiments, the lowest unoccupied molecular orbital energy level of the sensitizer is greater than or equal to -3.0 eV, and the lowest unoccupied molecular orbital energy level of the sensitizer is greater than or equal to -2.0 eV, for example, it can be -2.9 eV, -2.8 eV, -2.7 eV, -2.6 eV, -2.5 eV, -2.4 eV, -2.2 eV, -2.2 eV, -2.1 eV, etc.

[0103] By matching the highest occupied molecular orbital energy level range of the sensitizer with the highest occupied molecular orbital energy level range of the organic compound, and matching the lowest unoccupied molecular orbital energy level range of the sensitizer with the lowest unoccupied molecular orbital energy level range of the organic compound, carrier injection is facilitated.

[0104] In some embodiments, in the light-emitting layer 107 , the mass ratio of the organic compound, the sensitizer, and the host compound is 0.25-5:1-30:165-198.5, for example, 2:20:178.

[0105] In some embodiments, the sensitizer is preferably a phosphorescent material having phosphorescent emission, a maximum emission peak of an emission spectrum of the phosphorescent material being between 380 nanometers and 500 nanometers, and a phosphorescent lifetime of 1 microsecond to 100 milliseconds.

[0106] In some embodiments, when the sensitizer is preferably a phosphorescent material, the phosphorescent material contains at least one metal atom selected from the group consisting of Ir, Pd, Pt, Cu, Ag, and Au.

[0107] In some embodiments, the sensitizer may be selected from the following compounds:

[0108] In some embodiments, the anode is a hole-injecting electrode, and the anode can inject holes into the organic functional layer 103, such as the anode injecting holes into the hole injection layer 104, the hole transport layer 105, or the light-emitting layer 107. The anode may include at least one of a conductive metal, a conductive metal oxide, or a conductive polymer. The material of the anode includes, but is not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO (Indium Tin Oxide), aluminum-doped zinc oxide (AZO), etc., or other suitable and known anode materials, which can be easily selected and used by those skilled in the art. The material of the anode can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode can be patterned, such as patterned ITO conductive substrates are commercially available and can be used to prepare the light-emitting element of the present application.

[0109] In some embodiments, the cathode is an electrode that injects electrons, and the cathode can inject electrons into the organic functional layer, such as: the cathode injects electrons into the electron injection layer 110, the electron transport layer 109, or the light-emitting layer 107. The cathode may include at least one of a conductive metal or a conductive metal oxide. All materials that can be used as cathodes of organic electronic devices may be used as cathode materials for the device of the present application, and the materials of the cathode include but are not limited to at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, etc. The material of the cathode can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0110] In some embodiments, the hole injection layer 104 is used to promote the injection of holes from the anode into the light-emitting layer 107, and the hole injection layer 104 includes a hole injection material, which is a material that can receive holes injected from the positive electrode at a low voltage. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the material of the anode and the HOMO of the functional material of the film layer into which the holes are injected away from the anode (e.g., the hole transport material of the hole transport layer 105). The hole injection material includes, but is not limited to, at least one of metalloporphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, polyaniline-based conductive polymer, and polythiophene-based conductive polymer.

[0111] In some embodiments, the hole transport layer 105 can be used to transport holes to the light-emitting layer 107. The hole transport layer 105 includes a hole transport material that receives holes transferred from the anode or the hole injection layer 104 and transfers the holes to the light-emitting layer 107. The hole transport material is a material known in the art having high hole mobility, and the hole transport material may include but is not limited to at least one of an arylamine-based organic material, a conductive polymer, a block copolymer having both a conjugated portion and a non-conjugated portion, and the like.

[0112] In some embodiments, the electron transport layer 109 is used to transport electrons. The electron transport layer 109 includes an electron transport material that receives electrons injected from the negative electrode and transfers the electrons to the light-emitting layer 107. The electron transport material is a material known in the art with high electron mobility, and may include, but is not limited to, at least one of an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic free radical compound, a hydroxyflavone-metal complex, 8-hydroxyquinoline lithium (LiQ), and a benzimidazole-based compound.

[0113] In some embodiments, the electron injection layer 110 is used to inject electrons. The electron injection layer 110 includes an electron injection material. The electron injection material preferably has the ability to transport electrons, has the effect of injecting electrons from the negative electrode, has an excellent effect of injecting electrons into the light-emitting layer 107 or the light-emitting material, and has the ability to prevent excitons generated by the light-emitting layer 107 from migrating to the hole injection layer 104, and also has an excellent ability to form a thin film. The electron injection material includes, but is not limited to, at least one of 8-hydroxyquinoline lithium (LiQ), fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, azole, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylmethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0114] In some embodiments, the hole blocking layer 108 is used to block holes from reaching the negative electrode, and can generally be formed under the same conditions as the hole injection layer 104. The hole blocking layer 108 includes a hole blocking material, which includes but is not limited to at least one of a diazole derivative or a triazole derivative, a phenanthroline derivative, BCP, an aluminum complex, and the like.

[0115] In some embodiments, the light-emitting element 100 further includes an element substrate 111, on which the first electrode 101, the hole injection layer 104, the hole transport layer 105, the electron blocking layer 106, the light-emitting layer 107, the electron transport layer 109, the electron injection layer 110, and the second electrode 102 are sequentially stacked. The element substrate 111 can be a transparent substrate or an opaque substrate. When the element substrate 111 is a transparent substrate, a transparent light-emitting element can be fabricated. The element substrate 111 can be a rigid substrate or a flexible substrate with elasticity. The material of the element substrate 111 can include, but is not limited to, plastic, polymer, metal, semiconductor wafer, or glass. Preferably, the element substrate 111 includes at least one smooth surface for forming the anode on the surface.

[0116] The exemplary preparation methods of the organic compounds provided in this application are shown in the following exemplary embodiments 1 to 8.

[0117] Example 1

[0118] Organic compound M1 (molecular formula: C 32 H 16 N4, )

[0119] The synthetic route of organic compound M1 is as follows:

[0120] The specific synthesis steps of organic compound M1 are as follows:

[0121] Synthesis of intermediate 1-a:

[0122] Under argon protection, 2,6-dibromo-1,5-naphthyridine (28.7 g, 0.1 mol) was taken, an appropriate amount of anhydrous THF was added to dissolve it, the temperature was lowered to -78 ° C, the mixture was stirred for 30 min, n-butyl lithium (150 mL, 0.22 mol, 1.6 M) was added dropwise, the mixture was kept warm for 30 min, triisopropyl borate (41.4 g, 0.22 mol) was quickly added dropwise, the temperature was slowly raised to room temperature, and the reaction was carried out for 30 min; after the reaction was completed, the reaction solution was poured into a dilute hydrochloric acid aqueous solution and filtered to obtain a filter cake. The diboronic acid compound was obtained by air drying; the above product (21.6 g, 0.1 mol), 2-bromonitrobenzene (42.4 g, 0.21 mol), and potassium carbonate (69 g, 0.5 mol) were added to a 2 L three-necked flask; under argon protection, tetrakistriphenylphosphine palladium (1.1 g, 1%), 300 mL of deoxygenated water, and 1 L of deoxygenated toluene were added, and the mixture was heated to reflux for 12 h; the mixture was cooled to room temperature and filtered to obtain a solid product intermediate 1-a (35.2 g, yield 95%). MS (EI) (m / z) [M] + :Test value: 372.33.

[0123] Synthesis of intermediate 1-b:

[0124] In a 250 mL two-necked flask, intermediate 1-a (10.1 g, 27 mmol) and triphenylphosphine (35.41 g) were added. 100 mL of o-dichlorobenzene was added under argon protection. The mixture was refluxed at 180°C for 12 h under argon protection. The mixture was cooled to room temperature and filtered. The filter cake was intermediate 1-b (4.3 g, yield 51%). MS (EI) (m / z) [M] + :Test value: 308.52.

[0125] Synthesis of intermediate 1-c:

[0126] In a 250 mL two-necked flask, intermediate 1-b (3.1 g, 10 mmol), bromobenzene (3.3 g, 21 mmol), palladium acetate (0.2 g, 1 mmol), tri-tert-butylphosphine tetrafluoroborate (0.9 g, 3 mmol) and sodium tert-butoxide (2.4 g, 25 mmol) were added. 100 mL of dry toluene was added under argon protection, and the mixture was refluxed under argon protection for 24 h. After cooling to room temperature, the reaction solution was poured into 100 mL of saturated brine, extracted with dichloromethane, washed with saturated brine, and the organic phases were combined. The organic phases were concentrated and subjected to column chromatography to obtain intermediate 1-c (3.7 g, yield 82%). MS (EI) (m / z) [M] + :Test value: 460.72.

[0127] Synthesis of organic compound M1:

[0128] In a 100 mL single-necked flask, intermediate 1-c (2.3 g, 5 mmol), palladium acetate (0.2 g, 1 mmol), silver oxide (2.3 g, 10 mmol), and 35 mL of pivalic acid were added and heated with stirring at 160°C for 24 h. After cooling to room temperature, the reaction solution was poured into 250 mL of saturated sodium bicarbonate solution, stirred thoroughly until no bubbles were released, and filtered. The filter cake was dissolved in dichloromethane and filtered again. The filtrate was concentrated and column chromatography was performed to obtain organic compound M1 (1.1 g, 46% yield). Elemental analysis (PerkinElmer 2400, CHN mode) showed the following: Calculated: C, 84.19; H, 3.53; N, 12.27; Found: C, 84.55; H, 3.23; N, 12.97; MS (EI) (m / z) [M] + :Theoretical value: 456.51, tested value: 456.66.

[0129] Example 2

[0130] Organic compound M2 (molecular formula: C 50 H 36 N4, )

[0131] The synthetic route of organic compound M2 is as follows:

[0132] The specific synthesis steps of organic compound M2 are as follows:

[0133] Synthesis of intermediate 2-c:

[0134] In a 250 mL two-necked flask, intermediate 1-b (3.1 g, 10 mmol), 4'-bromo-2,4,6-trimethylbiphenyl (5.8 g, 21 mmol), palladium acetate (0.2 g, 1 mmol), tri-tert-butylphosphine tetrafluoroborate (0.9 g, 3 mmol) and sodium tert-butoxide (2.4 g, 25 mmol) were added. 100 mL of dry toluene was added under argon protection, and the mixture was refluxed under argon protection for 24 h. After cooling to room temperature, the reaction solution was poured into 100 mL of saturated brine, extracted with dichloromethane, washed with saturated brine, and the organic phases were combined. The organic phases were concentrated and subjected to column chromatography to obtain intermediate 2-c (5.9 g, 85%). MS (EI) (m / z) [M] + :Test value: 696.44.

[0135] Synthesis of organic compound M2:

[0136] In a 100 mL single-necked flask, intermediate 2-c (3.5 g, 5 mmol), palladium acetate (0.2 g, 1 mmol), silver oxide (2.3 g, 10 mmol), and 35 mL of pivalic acid were added and heated at 160°C with stirring for 24 h. After cooling to room temperature, the reaction solution was poured into 250 mL of saturated sodium bicarbonate solution, stirred thoroughly until no bubbles were released, and filtered. The filter cake was dissolved in dichloromethane and filtered again. The filtrate was concentrated and column chromatography was performed to obtain organic compound M2 (2.0 g, 59% yield). Elemental analysis (PerkinElmer 2400, CHN mode) showed the following: Calculated: C, 86.68; H, 5.24; N, 8.09; Found: C, 86.30; H, 5.53; N, 8.46; MS (EI) (m / z) [M] + : Theoretical value: 692.87, tested value: 692.63.

[0137] Example 3

[0138] Organic compound M3 (molecular formula: C 68 H 56 N4, )

[0139] The synthetic route of organic compound M3 is as follows:

[0140] The specific synthesis steps of organic compound M3 are as follows:

[0141] Synthesis of intermediate 3-a:

[0142] Substituting 2-bromonitrobenzene in the synthesis of Intermediate 1-a in Example 1 with 2-(3-bromo-4-nitrophenyl)-1,3,5-trimethylbenzene, the same method was used to obtain Intermediate 3-a (57.8 g, 95% yield). MS (EI) (m / z) [M]+ :Test value: 608.32.

[0143] Synthesis of intermediate 3-b:

[0144] In a 250 mL two-necked flask, intermediate 3-a (16.4 g, 27 mmol) and triphenylphosphine (35.41 g) were added. 100 mL of o-dichlorobenzene was added under argon protection. Under argon protection, the mixture was refluxed at 180°C for 12 h. The mixture was cooled to room temperature and filtered. The filter cake was intermediate 3-b (6.9 g, yield 47%). MS (EI) (m / z) [M] + :Test value: 544.23.

[0145] Synthesis of intermediate 3-c:

[0146] In a 250 mL two-necked flask, intermediate 3-b (5.4 g, 10 mmol), 2-(4-bromophenyl)-1,3,5-trimethylbenzene (5.8 g, 21 mmol), palladium acetate (0.2 g, 1 mmol), tri-tert-butylphosphine tetrafluoroborate (0.9 g, 3 mmol) and sodium tert-butoxide (2.4 g, 25 mmol) were added. 100 mL of dry toluene was added under argon protection, and the mixture was refluxed under argon protection for 24 h. After cooling to room temperature, the reaction solution was poured into 100 mL of saturated brine, extracted with dichloromethane, washed with saturated brine, and the organic phases were combined. The organic phases were concentrated and subjected to column chromatography to obtain intermediate 3-c (7.0 g, 75%). MS (EI) (m / z) [M] + :Test value: 933.23.

[0147] Synthesis of organic compound M3:

[0148] In a 100 mL single-necked flask, intermediate 3-c (4.6 g, 5 mmol), palladium acetate (0.2 g, 1 mmol), silver oxide (2.3 g, 10 mmol), and 35 mL of pivalic acid were added and heated with stirring at 160°C for 24 h. After cooling to room temperature, the reaction solution was poured into 250 mL of saturated sodium bicarbonate solution, stirred thoroughly until no bubbles were released, and filtered. The filter cake was dissolved in dichloromethane and filtered again. The filtrate was concentrated and column chromatography was performed to obtain organic compound M3 (2.0 g, 42% yield). Elemental analysis (PerkinElmer 2400, CHN mode) showed the following: Calculated: C, 87.90; H, 6.07; N, 6.03; Found: C, 87.53; H, 6.44; N, 6.80; MS (EI) (m / z) [M] + :Theoretical value: 929.22, tested value: 929.64.

[0149] Example 4

[0150] Organic compound M4 (molecular formula: C33 H 17 N3, )

[0151] The synthetic route of organic compound M4 is as follows:

[0152] The specific synthesis steps of organic compound M4 are as follows:

[0153] Synthesis of intermediate 4-a:

[0154] Substituting 2,8-dibromoquinoline for 2,6-dibromo-1,5-naphthyridine in the synthesis of intermediate 1-a in Example 1, intermediate 4-a (32.2 g, 92% yield) was obtained in the same manner. MS (EI) (m / z) [M] + :Test value: 373.31.

[0155] Synthesis of intermediate 4-b:

[0156] In a 250 mL two-necked flask, intermediate 4-a (10.1 g, 27 mmol) and triphenylphosphine (35.41 g) were added. 100 mL of o-dichlorobenzene was added under argon protection. Under argon protection, the mixture was refluxed at 180°C for 12 h. After cooling to room temperature, the mixture was filtered. The filter cake was intermediate 4-b (3.6 g, 43% yield). MS (EI) (m / z) [M] + :Test value: 309.23.

[0157] Synthesis of intermediate 4-c:

[0158] In a 250 mL two-necked flask, intermediate 4-b (3.1 g, 10 mmol), bromobenzene (3.3 g, 21 mmol), palladium acetate (0.2 g, 1 mmol), tri-tert-butylphosphine tetrafluoroborate (0.9 g, 3 mmol) and sodium tert-butoxide (2.4 g, 25 mmol) were added. 100 mL of dry toluene was added under argon protection, and the mixture was refluxed under argon protection for 24 h. After cooling to room temperature, the reaction solution was poured into 100 mL of saturated brine, extracted with dichloromethane, washed with saturated brine, and the organic phases were combined. The organic phases were concentrated and subjected to column chromatography to obtain intermediate 4-c (3.2 g, 70%). MS (EI) (m / z) [M] + :Test value: 461.43.

[0159] Synthesis of organic compound M4:

[0160] In a 100 mL single-necked flask, intermediate 4-c (2.3 g, 5 mmol), palladium acetate (0.2 g, 1 mmol), silver oxide (2.3 g, 10 mmol), and 35 mL of pivalic acid were added and heated with stirring at 160°C for 24 h. After cooling to room temperature, the reaction solution was poured into 250 mL of saturated sodium bicarbonate solution, stirred thoroughly until no bubbles were released, and filtered. The filter cake was dissolved in dichloromethane and filtered again. The filtrate was concentrated and column chromatography was performed to obtain organic compound M4 (0.91 g, 40% yield). Elemental analysis (PerkinElmer 2400, CHN mode) showed the following: Calculated: C, 87.01; H, 3.76; N, 9.22; Found: C, 87.33; H, 3.23; N, 9.85; MS (EI) (m / z) [M] + :Theoretical value: 455.52, tested value: 455.26.

[0161] Example 5

[0162] Organic compound M5 (molecular formula: C 69 H 57 N3, )

[0163] The synthetic route of organic compound M5 is as follows:

[0164] The specific synthesis steps of organic compound M5 are as follows:

[0165] Synthesis of intermediate 5-a:

[0166] The 2-bromonitrobenzene in the synthesis of intermediate 4-a in Example 4 was replaced by 2-(3-bromo-4-nitrophenyl)-1,3,5-trimethylbenzene to obtain intermediate 5-a (51.7 g, yield 85%) in the same manner. MS (EI) (m / z) [M] + :Test value: 609.31.

[0167] Synthesis of intermediate 5-b:

[0168] In a 250 mL two-necked flask, intermediate 4-a (16.4 g, 27 mmol) and triphenylphosphine (35.41 g) were added. 100 mL of o-dichlorobenzene was added under argon protection. Under argon protection, the mixture was refluxed at 180°C for 12 h. After cooling to room temperature, the mixture was filtered. The filter cake was intermediate 5-b (6.6 g, 45% yield). MS (EI) (m / z) [M] + :Test value: 545.23.

[0169] Synthesis of intermediate 5-c:

[0170] In a 250 mL two-necked flask, intermediate 5-b (5.4 g, 10 mmol), 2-(4-bromophenyl)-1,3,5-trimethylbenzene (5.8 g, 21 mmol), palladium acetate (0.2 g, 1 mmol), tri-tert-butylphosphine tetrafluoroborate (0.9 g, 3 mmol) and sodium tert-butoxide (2.4 g, 25 mmol) were added. 100 mL of dry toluene was added under argon protection, and the mixture was refluxed under argon protection for 24 h. After cooling to room temperature, the reaction solution was poured into 100 mL of saturated brine, extracted with dichloromethane, washed with saturated brine, and the organic phases were combined. The organic phases were concentrated and subjected to column chromatography to obtain intermediate 5-c (6.7 g, 72%). MS (EI) (m / z) [M] + :Test value: 931.43.

[0171] Synthesis of organic compound M5:

[0172] In a 100 mL single-necked flask, intermediate 5-c (4.6 g, 5 mmol), palladium acetate (0.2 g, 1 mmol), silver oxide (2.3 g, 10 mmol), and 35 mL of pivalic acid were added and heated with stirring at 160°C for 24 h. After cooling to room temperature, the reaction solution was poured into 250 mL of saturated sodium bicarbonate solution, stirred thoroughly until no bubbles were released, and filtered. The filter cake was dissolved in dichloromethane and filtered again. The filtrate was concentrated and column chromatography was performed to obtain organic compound M5 (1.9 g, 42% yield). Elemental analysis (PerkinElmer 2400, CHN mode) showed the following: Calculated: C, 89.28; H, 6.19; N, 4.53; Found: C, 89.45; H, 6.23; N, 9.32; MS (EI) (m / z) [M] + :Theoretical value: 927.45, tested value: 927.26.

[0173] Example 6

[0174] Organic compound M6 (molecular formula: C 54 H 44 N4, )

[0175] The synthetic route of organic compound M6 is as follows:

[0176] The specific synthesis steps of organic compound M6 are as follows:

[0177] Synthesis of intermediate 6-a:

[0178] Under argon protection, 2,6-dibromo-1,5-naphthyridine (28.7 g, 0.1 mol) was taken, an appropriate amount of anhydrous THF was added to dissolve it, the temperature was lowered to -78 ° C, the temperature was kept stirring for 30 min, n-butyl lithium (150 mL, 0.22 mol, 1.6 M) was added dropwise, the temperature was kept to react for 30 min, triisopropyl borate (41.4 g, 0.22 mol) was quickly added dropwise, the temperature was slowly raised to room temperature, and the reaction was carried out for 30 min; after completion of the reaction, the reaction solution was poured into a dilute hydrochloric acid aqueous solution, filtered to obtain a filter cake, and vacuum dried to obtain a diboric acid compound; the above product (21.6 g, 0 0.1 mol), 2-bromonitrobenzene (21.4 g, 0.11 mol), and potassium carbonate (69 g, 0.5 mol) were added to a 2L three-necked flask; under argon protection, tetrakistriphenylphosphine palladium (1.1 g, 1%), 150 mL of deoxygenated water, and 300 mL of deoxygenated toluene were added, and the mixture was heated under reflux for 12 hours. 2-Bromo-5-tert-butylnitrobenzene (27.4 g) was dissolved in 300 mL of deoxygenated toluene, mixed with 150 mL of deoxygenated water, and then added to the reaction mixture, and the mixture was heated under reflux for another 12 hours. The temperature was cooled to room temperature and filtered to obtain the solid product intermediate 6-a (36.4 g, 85% yield). MS (EI) (m / z) [M] + :Test value: 428.29.

[0179] Synthesis of intermediate 6-b:

[0180] In a 250 mL two-necked flask, intermediate 6-a (11.6 g, 27 mmol) and triphenylphosphine (35.41 g) were added. 100 mL of o-dichlorobenzene was added under argon protection. Under argon protection, the mixture was refluxed at 180°C for 12 h. After cooling to room temperature, the mixture was filtered. The filter cake was intermediate 6-b (3.7 g, 38% yield). MS (EI) (m / z) [M] + :Test value: 364.11.

[0181] Synthesis of intermediate 6-c:

[0182] To a 250 mL two-necked flask were added intermediate 6-b (3.6 g, 10 mmol), 2-(4-bromophenyl)-1,3,5-trimethylbenzene (5.8 g, 21 mmol), palladium acetate (0.2 g, 1 mmol), tri-tert-butylphosphine tetrafluoroborate (0.9 g, 3 mmol), and sodium tert-butoxide (2.4 g, 25 mmol). Under argon, 100 mL of dry toluene was added, and the mixture was refluxed under argon for 24 h. After cooling to room temperature, the reaction mixture was poured into 100 mL of saturated brine, extracted with dichloromethane, washed with saturated brine, and the organic phases were combined. The organic phases were concentrated and purified by column chromatography to yield intermediate 6-c (5.7 g, 77%). MS (EI) (m / z) [M] + :Test value: 753.12.

[0183] Synthesis of organic compound M6:

[0184] In a 100 mL single-necked flask, intermediate 6-c (3.8 g, 5 mmol), palladium acetate (0.2 g, 1 mmol), silver oxide (2.3 g, 10 mmol), and 35 mL of pivalic acid were added and heated with stirring at 160°C for 24 h. After cooling to room temperature, the reaction solution was poured into 250 mL of saturated sodium bicarbonate solution, stirred thoroughly until no bubbles were released, and filtered. The filter cake was dissolved in dichloromethane and filtered again. The filtrate was concentrated and column chromatography was performed to obtain organic compound M6 (1.3 g, 36% yield). Elemental analysis (PerkinElmer 2400, CHN mode) showed the following: Calculated: C, 86.60; H, 5.92; N, 7.48; Found: C, 86.69; H, 5.74; N, 7.53; MS (EI) (m / z) [M] + :Theoretical value: 748.97, tested value: 749.03.

[0185] Example 7

[0186] Organic compound M7 (molecular formula: C 51 H 37 N3, )

[0187] The synthetic route of organic compound M7 is as follows:

[0188] The specific synthesis steps of organic compound M7 are as follows:

[0189] Synthesis of intermediate 7-c:

[0190] In a 250 mL two-necked flask, intermediate 4-b (3.1 g, 10 mmol), 2-(4-bromophenyl)-1,3,5-trimethylbenzene (5.8 g, 21 mmol), palladium acetate (0.2 g, 1 mmol), tri-tert-butylphosphine tetrafluoroborate (0.9 g, 3 mmol) and sodium tert-butoxide (2.4 g, 25 mmol) were added. 100 mL of dry toluene was added under argon protection, and the mixture was refluxed under argon protection for 24 h. After cooling to room temperature, the reaction solution was poured into 100 mL of saturated brine, extracted with dichloromethane, washed with saturated brine, and the organic phases were combined. The organic phases were concentrated and subjected to column chromatography to obtain intermediate 7-c (5.6 g, 81%). MS (EI) (m / z) [M] + :Test value: 695.39.

[0191] Synthesis of organic compound M7:

[0192] In a 100 mL single-necked flask, intermediate 7-c (3.5 g, 5 mmol), palladium acetate (0.2 g, 1 mmol), silver oxide (2.3 g, 10 mmol), and 35 mL of pivalic acid were added and heated at 160°C with stirring for 24 h. After cooling to room temperature, the reaction solution was poured into 250 mL of saturated sodium bicarbonate solution, stirred thoroughly until no bubbles were released, and filtered. The filter cake was dissolved in dichloromethane and filtered again. The filtrate was concentrated and column chromatography was performed to obtain organic compound M7 (1.1 g, 33% yield). Elemental analysis (PerkinElmer 2400, CHN mode) showed the following: Calculated: C, 88.54; H, 5.39; N, 6.07; Found: C, 88.48; H, 5.45; N, 6.04; MS (EI) (m / z) [M] + :Theoretical value: 691.30, tested value: 691.39.

[0193] Example 8

[0194] Organic compound M8 (molecular formula: C 57 H 39 N5, )

[0195] The synthetic route of organic compound M8 is as follows:

[0196] The specific synthesis steps of organic compound M8 are as follows:

[0197] Synthesis of intermediate 8-c:

[0198] To a 250 mL two-necked flask, intermediate 5-b (5.4 g, 10 mmol), 2-bromoquinoline (4.3 g, 21 mmol), palladium acetate (0.2 g, 1 mmol), tri-tert-butylphosphine tetrafluoroborate (0.9 g, 3 mmol), and sodium tert-butoxide (2.4 g, 25 mmol) were added. 100 mL of dry toluene was added under argon protection, and the mixture was refluxed under argon protection for 24 h. After cooling to room temperature, the reaction solution was poured into 100 mL of saturated brine, extracted with dichloromethane, washed with saturated brine, and the organic phases were combined. The organic phases were concentrated and purified by column chromatography to obtain intermediate 8-c (5.8 g, 73%). MS (EI) (m / z) [M] + :Test value: 797.43.

[0199] Synthesis of organic compound M8:

[0200] In a 100 mL single-necked flask, intermediate 8-c (3.9 g, 5 mmol), palladium acetate (0.2 g, 1 mmol), silver oxide (2.3 g, 10 mmol), and 35 mL of pivalic acid were added and heated with stirring at 160°C for 24 h. After cooling to room temperature, the reaction solution was poured into 250 mL of saturated sodium bicarbonate solution, stirred thoroughly until no bubbles were released, and filtered. The filter cake was dissolved in dichloromethane and filtered again. The filtrate was concentrated and column chromatography was performed to obtain organic compound M (0.5 g, 12% yield). Elemental analysis (PerkinElmer 2400, CHN mode) showed the following: Calculated: C, 86.23; H, 4.95; N, 8.82; Found: C, 86.46; H, 4.82; N, 8.73; MS (EI) (m / z) [M] + :Theoretical value: 793.32, tested value: 793.39.

[0201] Comparative Example 1

[0202] Comparative Compound 1 was used as a comparative example for Examples 1 to 8. Comparative Compound 1 is a common fluorescent molecule that does not have microsecond delayed fluorescence. The structural formula of Comparative Compound 1 is:

[0203] The organic compounds M1 to M8 obtained in Examples 1 to 8 and the comparative compound 1 were subjected to steady-state fluorescence spectrum tests (test conditions: using a Hitachi fluorescence spectrometer F-4600 at room temperature, using 360 nm excitation, and the sample was 10 -5 mol / L dilute toluene solution) and luminescence lifetime test (test conditions: doping the mCBP film with 1% mass fraction of organic compounds M1 to M8 and comparative compound 1, transient luminescence spectrum test), and the test results are shown in Figure 2 and Table 1.

[0204] Table 1: Maximum emission wavelengths (λ) of organic compounds M1 to M8 and comparative compound 1 peak ), full width at half maximum (FWHM) and luminescence lifetime in solid-state thin film state (τ film )

[0205] It can be seen from the results in Table 1 and Figure 2 that the organic compounds M1 to M8 provided in Examples 1 to 8 of the present application have microsecond delayed fluorescence, and the maximum emission wavelengths of the organic compounds M1 to M8 are between 452nm and 469nm. Compared with the comparative compound 1, they are located in the blue light-emitting region and have longer maximum emission wavelengths, which can better meet commercial needs; at the same time, the half-peak width of the emission spectrum of the organic compounds M1 to M8 is between 9nm and 20nm, with an extremely narrow half-peak width, which is conducive to being used as a blue light-emitting material with higher color purity in light-emitting elements.

[0206] The exemplary manufacturing steps of the light-emitting element provided in this application are shown in the following exemplary embodiment 9.

[0207] Example 9

[0208] In the light-emitting element provided in this embodiment, ITO (indium tin oxide) is used as the anode; HATCN is used as the material of the hole injection layer; TAPC is used as the material of the hole transport layer; TCTA is used as the material of the electron blocking layer; mCBP is used as the main material in the light-emitting layer of the corresponding light-emitting element, the organic compounds M1 to M8 and the comparative compound 1 in Examples 1 to 8 are used as the guest materials in the light-emitting layer of the corresponding light-emitting element, respectively, BD-01 is used as a sensitizer in some light-emitting elements; TPBI is used as the material of the hole blocking layer; ANT-BIZ is used as the material of the electron transport layer; Liq is used as the material of the electron injection layer; Al is used as the cathode, and under high vacuum conditions, a hole injection layer (5 nm), a hole transport layer (30 nm), an electron blocking layer (15 nm), a light-emitting layer (20 nm), a hole blocking layer (10 nm), an electron transport layer (40 nm), an electron injection layer (1.5 nm) and a cathode (100 nm) are sequentially evaporated on the cleaned ITO to form.

[0209] Specifically, in this embodiment, light-emitting elements 1 to 16 and comparative element 1 were obtained through the above steps. The guest materials used in light-emitting elements 1 to 8 were organic compounds M1 to M8, respectively, and the guest material used in comparative element 1 was comparative compound 1. The mass ratio of the host material to the guest material in the light-emitting layers of light-emitting elements 1 to 8 and comparative element 1 was 198:2. The guest materials used in light-emitting elements 9 to 16 were organic compounds M1 to M8, respectively, and the mass ratio of the host material to the sensitizer and guest material in the light-emitting layers of light-emitting elements 11 to 16 was 178:20:2.

[0210] Specifically, HATCN, TAPC, TCTA, mCBP, TPBI, BD-01, ANT-BIZ, Liq, and comparative compound 1 are all commercially available or prepared by known synthetic methods. The chemical structures of HATCN, TAPC, TCTA, mCBP, TPBI, BD-01, and ANT-BIZ are as follows:

[0211] In this embodiment, light emitting elements 1 to 16 and comparative element 1 were tested at a current density of 10 mA / cm 2The current-voltage (JV) characteristic test was carried out under the same brightness, and the driving voltage (voltage (V)), luminous efficiency (EQE (%)), and the time taken for the brightness to drop from the initial brightness to 95% of the initial brightness (LT95 (h)) of each light-emitting element and the comparison element were obtained. The specific results are shown in Table 2.

[0212] Table 2: Performance data of Light-emitting Elements 1 to 16 and Comparative Element 1

[0213] As can be seen from Table 2, the light-emitting elements 1 to 16 obtained in the present application by using guest materials M1 to M8 in the light-emitting layer have significantly improved luminous efficiency compared to the comparative element 1 under the condition of equivalent driving voltage; further, the luminous efficiency of light-emitting elements 1 to 8 is 7.9% to 9.4%, and the luminous efficiency of light-emitting elements 9 to 16 is 21.2% to 27.7%, indicating that the addition of the sensitizer effectively improves the luminous efficiency of the light-emitting element; at the same time, the time taken for the brightness of light-emitting elements 1 to 8 and light-emitting elements 9 to 16 to decrease from the same initial brightness to 95% of the initial brightness is all in the range of 83h to 107h, which is significantly improved compared to the time taken for the brightness of the comparative element 1 to decrease from the same initial brightness to 95% of the initial brightness. In addition, compared with light-emitting elements 1 to 8, when using the same guest material, the luminous efficiency and the time taken for the brightness to drop from the same initial brightness to 95% of the initial brightness of light-emitting elements 9 to 16 were significantly increased, indicating that the addition of the sensitizer is beneficial to stabilizing the light-emitting elements, improving the luminous efficiency of the light-emitting elements and extending the life of the light-emitting elements.

[0214] The light-emitting element disclosed in the embodiment of the present application uses the organic compound with a multiple resonance effect. The organic compound adopts a nitrogen-containing fused ring as the core structure. By introducing nitrogen atoms, the triplet energy level and multiple resonance effect of the organic compound molecule are adjusted, thereby improving the material properties of the organic compound, thereby improving the luminous efficiency of the display panel using the organic compound and extending the service life.

[0215] Referring to FIG. 3 , an embodiment of the present application further discloses a display panel 10 , which includes any of the above-mentioned light-emitting elements 100 .

[0216] In some embodiments, the display panel 10 further includes an array substrate 200 located on one side of the light emitting element 100 .

[0217] The array substrate 200 includes a substrate 210 , and the light emitting element 100 is disposed on one side of the substrate 210 .

[0218] In some embodiments, the first electrode layer 101 of the light-emitting element 100 is arranged on one side of the substrate 210, the second electrode layer 102 is arranged on the side of the first electrode layer 101 away from the substrate 210, and the organic functional layer 103 is arranged between the first electrode layer 101 and the second electrode layer 102.

[0219] In some embodiments, the light emitting element 100 is a blue light emitting element B, and the display panel 10 further includes a red light emitting element R and a green light emitting element G.

[0220] In some embodiments, the array substrate 200 also includes a thin film transistor layer 220 located between the light-emitting element 100 and the substrate 210, and the thin film transistor layer 220 includes a thin film transistor, which is electrically connected to the first electrode layer 101 of the light-emitting element 100 to control the light emission of the light-emitting element 100.

[0221] In some embodiments, the display panel 10 further includes an encapsulation layer 300 located on a side of the light emitting element 100 away from the array substrate 200 and covering the light emitting element 100 .

[0222] In some embodiments, the display panel 10 further includes a polarizer layer 400 located on a side of the encapsulation layer 300 away from the light-emitting element 100, and a cover layer 500 located on a side of the polarizer layer 400 away from the light-emitting element 100. The polarizer layer 400 may be replaced by a color filter layer, which may include multiple color resists and a black matrix located on both sides of the color resists.

[0223] The display panel disclosed in the embodiment of the present application uses an organic compound with a multiple resonance effect in the light-emitting element. The organic compound adopts a nitrogen-containing fused ring as the core structure. By introducing nitrogen atoms, the triplet energy level and multiple resonance effect of the organic compound molecule are adjusted, thereby improving the material properties of the organic compound, thereby improving the luminous efficiency of the display panel using the organic compound and extending its service life.

[0224] The embodiments of the present application disclose an organic compound and a display panel. The organic compound has a structure as shown in general formula (1): The present application uses an organic compound with a multiple resonance effect, which adopts a nitrogen-fused ring as the core structure. By introducing nitrogen atoms, the triplet energy level and multiple resonance effect of the organic compound molecule are adjusted, thereby improving the material properties of the organic compound, thereby improving the luminous efficiency of the display panel using the organic compound and extending the service life.

[0225] The above is a detailed introduction to an organic compound and a display panel provided in the embodiments of the present application. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the method of the present application and its core idea. At the same time, for those skilled in the art, based on the ideas of the present application, there will be changes in the specific implementation methods and application scope. In summary, the content of this specification should not be understood as a limitation on the present application.

Claims

1. An organic compound having a structure as shown in general formula (1): in, X1 is selected from C or N; A1, A2, A3 and A4 are each independently selected from a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms; R1, R2, R3 and R4, at each occurrence, are independently selected from H, D, T, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 2 to 30 carbon atoms; m, n, p, and q are each independently selected from any integer from 0 to 11; When m is greater than or equal to 2, adjacent R1s may form a ring or not; When n is greater than or equal to 2, adjacent R2s may form a ring or not; When p is greater than or equal to 2, adjacent R3 may form a ring or not; When q is greater than or equal to 2, adjacent R4 may form a ring or may not form a ring.

2. The organic compound according to claim 1, wherein When X1 is selected from N, A1 is the same as A4, and A2 is the same as A3; When X1 is selected from C, A1 is the same as A2, and A3 is the same as A4.

3. The organic compound according to claim 2, wherein When X1 is selected from N, R1 is the same as R4, and R2 is the same as R3; When X1 is selected from C, R1 is the same as R2, and R3 is the same as R4.

4. The organic compound according to any one of claims 1 to 3, wherein A1, A2, A3 and A4 are independently selected from any one of the structures shown in (1-1) to (1-4): wherein Z is selected from C, CR5 or N; Y is selected from CR6R7, O or S; R5, at each occurrence, is independently selected from H, D, T, a halogen group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaromatic group having 2 to 30 carbon atoms, and adjacent R5 may be cyclic or acyclic; Each occurrence of R6 and R7 is independently selected from substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, and substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms.

5. The organic compound according to claim 4, wherein A1, A2, A3 and A4 are independently selected from any one of the following structures: Among them, Z1 is selected from CR5.

6. The organic compound according to claim 4 or 5, wherein Each occurrence of R5 is independently selected from H, D, T, F, Cl, cyano, methyl, ethyl, tert-butyl, n-pentyl, cyclohexyl, ethynyl or the following groups: Wherein, "*" indicates the connection site.

7. The organic compound according to claim 4, wherein When at least two adjacent R1s form a ring, the ring formed by at least two adjacent R1s forms a parallel ring structure with A1; when at least two adjacent R2s form a ring, the ring formed by at least two adjacent R2s forms a parallel ring structure with A2; when at least two adjacent R3s form a ring, the ring formed by at least two adjacent R3s forms a parallel ring structure with A3; when at least two adjacent R4s form a ring, the ring formed by at least two adjacent R4s forms a parallel ring structure with A4.

8. The organic compound according to claim 7, wherein When at least two adjacent R5's form a ring, at least two adjacent R5's form a substituted or unsubstituted alicyclic group having 5 to 7 carbon atoms.

9. The organic compound according to claim 7, wherein When at least two adjacent R5s form a ring, the ring structure formed by the at least two adjacent R5s and the adjacent A1, A2, A3 or A4 can be independently selected from a substituted or unsubstituted aromatic group having 10 to 15 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 8 to 18 carbon atoms.

10. The organic compound according to claim 7, wherein When at least two adjacent R5s form a ring, the ring structure formed by the at least two adjacent R5s and the adjacent A1, A2, A3 or A4 can be selected from the following structures:

11. The organic compound according to claim 4, wherein R6 and R7, when present, are each independently selected from methyl or phenyl.

12. The organic compound according to claim 1, wherein The organic compound is selected from the following compounds:

13. The organic compound according to claim 1, wherein The highest occupied molecular orbital energy level of the organic compound is greater than or equal to -6.0 eV, and the highest occupied molecular orbital energy level of the organic compound is less than or equal to -5.0 eV; The lowest unoccupied molecular orbital energy level of the organic compound is greater than or equal to -3.0 eV, and the lowest unoccupied molecular orbital energy level of the organic compound is less than or equal to -2.0 eV.

14. The organic compound according to claim 1, wherein The fluorescence lifetime of the solid-state thin film formed by the organic compound ranges from 1 microsecond to 100 milliseconds.

15. A display panel comprising: substrate; A first electrode layer is provided on one side of the substrate; a second electrode layer, disposed on a side of the first electrode layer away from the substrate; an organic functional layer, disposed between the first electrode layer and the second electrode layer; Wherein, the material of the organic functional layer includes the organic compound according to claim 1.

16. The display panel according to claim 15, wherein: The organic functional layer at least includes a light-emitting layer. The light-emitting layer includes a host material and a guest material. The guest material is one or more of the organic compounds represented by the general formula (1).

17. The display panel according to claim 16, wherein: The mass ratio of the host material to the guest material ranges from 199.5:0.5 to 190:

10.

18. The display panel according to claim 15, wherein: The organic functional layer at least includes a light-emitting layer, which includes a host material, a guest material and a sensitizer. The guest material is one or more of the organic compounds represented by the general formula (1), and the sensitizer is at least one of a phosphorescent material and a thermally activated delayed fluorescent material.

19. The display panel according to claim 18, wherein: The sensitizer is a phosphorescent material containing at least one of Ir, Pd, Pt, Cu, Ag and Au metal atoms.

20. The display panel according to claim 18, wherein The sensitizer may be selected from the following compounds:

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