Organic compound and display panel

Abstract

Disclosed in the embodiments of the present invention are an organic compound and a display panel. The organic compound has a structure represented by general formula (1).

Description

Organic compounds and display panels Technical Field

[0001] The present application relates to the field of display, and in particular to an organic compound and a display panel. Background Art

[0002] 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.

[0003] Therefore, an organic compound and a display panel are urgently needed to solve the above technical problems. Technical issues

[0004] The present invention provides an organic compound and a display panel. By providing an organic compound with a multi-resonance effect, and by lengthening the distance between B and B in the organic compound and / or introducing N to interrupt conjugation to weaken para-electron coupling, the material properties of the organic compound are improved, thereby enhancing the luminous efficiency and color purity of the display panel using the organic compound and extending the service life. Technical Solutions

[0005] To solve the above problems, the technical solutions provided by this application are as follows:

[0006] The present invention provides an organic compound having a structure as shown in general formula (1):

[0007] Wherein, M1 and M2 are independently selected from B and N;

[0008] Y1 and Y2 are independently selected from C and N, and at least one of Y1 and Y2 is selected from N;

[0009] A1, A2, A3 and A4 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms. A1 and A2 may or may not form a ring, and A3 and A4 may or may not form a ring.

[0010] When M1 is selected from B, X1 and X2 are each independently selected from an electron-donating group;

[0011] When M1 is selected from N, X1 and X2 are each independently selected from an electron-withdrawing group;

[0012] When M2 is selected from B, X3 and X4 are each independently selected from an electron-donating group;

[0013] When M2 is selected from N, X3 and X4 are each independently selected from an electron-withdrawing group.

[0014] The present invention further provides a display panel, comprising:

[0015] substrate;

[0016] A first electrode layer is provided on one side of the substrate;

[0017] a second electrode layer, disposed on a side of the first electrode layer away from the substrate;

[0018] an organic functional layer, disposed between the first electrode layer and the second electrode layer;

[0019] Wherein, the material of the organic functional layer includes at least one organic compound as mentioned above. BRIEF DESCRIPTION OF THE DRAWINGS

[0020] FIG1 is a schematic structural diagram of a light-emitting element provided in an embodiment of the present invention;

[0021] FIG2 is a schematic structural diagram of a display panel provided by an embodiment of the present invention. Modes for Carrying Out the Invention

[0022] This application provides an organic compound and a display panel. To make the purpose, technical solution, and effects of this application more clear and explicit, the application is further described in detail below with reference to the accompanying drawings and examples. It should be understood that the specific examples described herein are only used to explain this application and are not intended to limit this application.

[0023] In the present invention, aryl, aromatic group, aromatic group, aromatic family, and aromatic ring system have the same meaning and can be interchanged.

[0024] In the present invention, heteroaryl, heteroaromatic group, heteroaromatic group, heteroaromatic family, and heteroaromatic ring system have the same meaning and can be interchanged.

[0025] In the present invention, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0026] In the present invention, 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.

[0027] In the present invention, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it should be 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, alkyl containing 1-20 carbon atoms, heterocyclic group containing 3-20 carbon atoms, aromatic group containing 6-20 carbon atoms, heteroaromatic group 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, alkyl groups containing 1 to 10 carbon atoms, heterocyclic groups containing 3 to 20 carbon atoms, aromatic groups containing 6 to 20 carbon atoms, heteroaromatic groups containing 5 to 20 carbon atoms. Preferably, R is selected from, but not limited to, deuterium atoms, cyano, isocyano, nitro or halogen, alkyl groups containing 1 to 10 carbon atoms, heterocyclic groups containing 3 to 10 carbon atoms, aromatic groups containing 6 to 20 carbon atoms, heteroaromatic groups containing 5 to 20 carbon atoms, silanyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups may be further substituted with substituents acceptable in the art.

[0028] In the present invention, "aromatic group or aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom, and 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 derivatives thereof. 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.

[0029] In the present invention, "heteroaromatic group or heteroaromatic group" refers to an aromatic group in which at least one carbon atom is replaced by a non-carbon atom, and the non-carbon atom may be a N atom, an O atom, an S atom, etc. For example, "substituted or unsubstituted heteroaryl group having 5 to 40 ring atoms" refers to 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,

[0030] In the present invention, "alkyl" may refer to a linear, branched 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 1-9The term "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-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pent ... -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, 3,7-dimethyloctyl, cyclooctyl, n-nonyl, n-decyl, adamantyl, 2-ethyldecyl, 2-butyldecyl, 2-hexyldecyl, 2-octyldecyl, n-undecyl, n-dodecyl, 2-ethyldodecyl, 2-butyldodecyl, 2- Hexyldodecyl, 2-octyldodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, 2-ethylhexadecyl, 2-butylhexadecyl, 2-hexylhexadecyl, 2-octylhexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl, n-eicosyl, 2-ethyleicosyl, 2-butyleicosyl, 2-hexyleicosyl, 2-octyleicosyl, n-heneicosyl, n-docosyl, n-tricosyl, n-tetracosyl, n-pentacosyl, n-hexacosyl, n-heptacosyl, n-octacosyl, n-nonacosyl, n-triacontyl, etc.

[0031] In the present invention, "*" connected to a single bond indicates a connection or fusion site.

[0032] In the present invention, 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.

[0033] In the present invention, when the fusion site is not specified in the 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 ortho position in the group are used as the fusion site.

[0034] In the present invention, 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.

[0035] In the present invention, 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.

[0036] According to the present invention, the cyclic alkyl group or cycloalkyl group has the same meaning and can be interchanged.

[0037] In the present invention, "adjacent groups" means that there is no substitutable site between two substituents.

[0038] In the present invention, "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,

[0039] In the present invention, the HOMO (Highest Occupied Molecular Orbital) and LUMO (Lowest Unoccupied Molecular Orbital) energy levels can be measured by photoelectric effect, such as XPS (X-ray Photoelectron Spectroscopy) and UPS (Ultraviolet Photoelectron Spectroscopy) or by cyclic voltammetry (CV). In addition, quantum chemical methods, such as density functional theory (hereinafter referred to as DFT, Density Functional Theory), are also effective methods for calculating molecular orbital energy levels.

[0040] The luminescence lifetime of organic materials can be obtained by techniques such as time-correlated single photon counting (TCSPC).

[0041] The present invention provides an organic compound with a multiple resonance effect, and improves the material properties of the organic compound by lengthening the distance between B and B in the organic compound and / or introducing N to interrupt the conjugation to weaken the para-electron coupling, thereby improving the luminous efficiency and color purity of the display panel using the organic compound and extending the service life.

[0042] An embodiment of the present invention provides an organic compound having a structure as shown in general formula (1):

[0043] Wherein, M1 and M2 are independently selected from B and N;

[0044] Y1 and Y2 are independently selected from C and N, and at least one of Y1 and Y2 is selected from N;

[0045] A1, A2, A3 and A4 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms. A1 and A2 may or may not form a ring, and A3 and A4 may or may not form a ring.

[0046] When M1 is selected from B, X1 and X2 are each independently selected from an electron-donating group;

[0047] When M1 is selected from N, X1 and X2 are each independently selected from an electron-withdrawing group;

[0048] When M2 is selected from B, X3 and X4 are each independently selected from an electron-donating group;

[0049] When M2 is selected from N, X3 and X4 are each independently selected from an electron-withdrawing group.

[0050] 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, its 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), which lengthens the distance between B and B in the organic compound and / or introduces N to interrupt the conjugation, weakens the para-electronic coupling, is conducive to the blue shift of the maximum emission wavelength of the organic compound and reduces the energy loss caused by non-radiative transitions, 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.

[0051] The present invention provides an organic compound with a multiple resonance effect, and improves the material properties of the organic compound by lengthening the distance between B and B in the organic compound and / or introducing N to interrupt the conjugation to weaken the para-electron coupling, thereby improving the luminous efficiency and color purity of the display panel using the organic compound and extending the service life.

[0052] In some embodiments, M1 and M2 are independently selected from B and N, and M1 and M2 may be the same or different. Preferably, M1 and M2 are the same, that is, M1 and M2 are simultaneously selected from B or M1 and M2 are simultaneously selected from N. When M1 and M2 are simultaneously selected from B, the distance between B and B in the organic compound is lengthened, weakening the para-electronic coupling, which is beneficial to the blue shift of the maximum emission wavelength of the organic compound and reducing the non-radiative transition caused by the group connected to blue-shift the organic compound; and when M1 and M2 are simultaneously selected from B, the difference in electronegativity between B and N in the organic compound compared to C is beneficial to enhancing the multiple resonance effect of the organic compound, thereby further narrowing the emission spectrum of the organic compound and further suppressing the intensity of the shoulder peak at the long wavelength in the emission spectrum of the organic compound, thereby improving the color purity of the luminescence of the organic compound. When M1 and M2 are both selected from N, the intramolecular conjugation of the organic compound is interrupted, the para-electronic coupling is weakened, which is beneficial to the blue shift of the maximum emission wavelength of the organic compound and reduces the non-radiative transition caused by the group connected to blue-shift the organic compound.

[0053] In some embodiments, when M1 is selected from B, X1 and X2 are each independently selected from an electron-donating group; when M2 is selected from B, X3 and X4 are each independently selected from an electron-donating group.

[0054] In some embodiments, when M1 is selected from N, X1 and X2 are each independently selected from an electron-withdrawing group; when M2 is selected from N, X3 and X4 are each independently selected from an electron-withdrawing group.

[0055] In some embodiments, the electron-donating group increases the electron cloud density on the benzene ring when replacing hydrogen on the benzene ring; the electron-withdrawing group decreases the electron cloud density on the benzene ring when replacing hydrogen on the benzene ring.

[0056] In some embodiments, when M1 is selected from B, X1 and X2 are each independently selected from at least one of N—R1, O, and S; when M2 is selected from B, X3 and X4 are each independently selected from at least one of N—R1, O, and S.

[0057] When M1 is selected from N, X1 and X2 are each independently selected from at least one of B-R1, a carbonyl group, a sulfone group, and a sulfoxide group; when M2 is selected from N, X3 and X4 are each independently selected from at least one of B-R1, a carbonyl group, a sulfone group, and a sulfoxide group.

[0058] wherein each occurrence of R1 is independently selected from H, D, T, a substituted or unsubstituted straight-chain alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted branched alkyl group or cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 12 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 5 to 12 carbon atoms.

[0059] In some embodiments, when R1 is selected from substituted or unsubstituted linear alkyl groups having 1 to 5 carbon atoms, R1 is preferably selected from unsubstituted linear alkyl groups having 1 to 5 carbon atoms, for example: methyl, ethyl, n-propyl, n-butyl, n-pentyl, etc.

[0060] In some embodiments, when R1 is selected from a substituted or unsubstituted branched alkyl or cycloalkyl group having 3 to 12 carbon atoms, R1 is selected from an unsubstituted branched alkyl or cycloalkyl group having 3 to 12 carbon atoms. Among them, R1 is preferably selected from an unsubstituted alkyl group having 3 to 5 carbon atoms, such as isopropyl, sec-butyl, tert-butyl, isobutyl, isopentyl, neopentyl, tert-pentyl, etc. R1 is preferably selected from a cycloalkyl group having 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.

[0061] In some embodiments, when R1 is selected from a substituted or unsubstituted aromatic group having 6 to 15 carbon atoms, R1 is preferably selected from a substituted or unsubstituted aromatic group having 6 or 12 ring atoms or a substituted or unsubstituted aromatic group having 10 ring atoms, for example, unsubstituted phenyl, unsubstituted naphthyl, etc., wherein "*" represents a bonding site, n is selected from 1, 2, 3, 4, 5, R7 is selected from D, T, an alkyl group having 1 to 6 carbon atoms (such as a straight-chain alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 6 carbon atoms, or a cycloalkyl group, etc.) or a phenyl group; m is selected from any integer between 1 and 9, and R8 is selected from D, T, a methyl group or an ethyl group, etc.

[0062] In some embodiments, when R1 is selected from a substituted or unsubstituted heteroaromatic group having 5 to 15 carbon atoms, R1 is preferably selected from an unsubstituted heteroaromatic group having 5 to 12 carbon atoms. For example, R1 can be selected from a pyridyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a naphthyl group, a quinolyl group, a naphthyridinyl group, and the like.

[0063] In some embodiments, A1, A2, A3 and A4 are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms; preferably, A1, A2, A3 and A4 are independently selected from substituted or unsubstituted aromatic groups having 6 to 15 carbon atoms, for example: wait.

[0064] In some embodiments, A1, A2, A3 and A4 are independently selected from substituted or unsubstituted heteroaromatic groups having 5 to 30 carbon atoms; preferably, A1, A2, A3 and A4 are independently selected from substituted or unsubstituted heteroaromatic groups having 5 to 18 carbon atoms, for example: wait.

[0065] In some embodiments, at least one of A1 to A4 adjacent to R1 is bridged to R1 via a single bond or a first bridging group. For example, when X1 is selected from N-R1 or B-R1, A1 can be bridged to R1 via a single bond or the first bridging group; when X2 is selected from N-R1 or B-R1, A2 can be bridged to R1 via a single bond or the first bridging group; when X3 is selected from N-R1 or B-R1, A3 can be bridged to R1 via a single bond or the first bridging group; and when X4 is selected from N-R1 or B-R1, A4 can be bridged to R1 via a single bond or the first bridging group.

[0066] In some embodiments, each occurrence of the first bridging group is independently selected from at least one of N-R2, CR3R4, SiR5R6, O, S, Se, Te, a carbonyl group, a sulfone group, and a sulfoxide group, wherein R2, R3, R4, R5, and R6 are independently selected from H, D, T, a substituted or unsubstituted linear alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted branched alkyl group or cycloalkyl group having 3 to 6 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 15 carbon atoms.

[0067] In some embodiments, each occurrence of R2, R3, R4, R5, and R6 is independently selected from H, D, T, an unsubstituted linear or branched alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 10 carbon atoms, or a substituted or unsubstituted heteroaromatic group having 6 to 12 carbon atoms.

[0068] In some embodiments, each occurrence of R2, R3, R4, R5, and R6 is independently selected from methyl and phenyl.

[0069] In some embodiments, each occurrence of the first bridging group can be independently selected from At least one of O, S, Se, Te, carbonyl, sulfone, sulfoxide and the like.

[0070] In some embodiments, A1 and A2 are bridged by a single bond or a second bridging group.

[0071] In some embodiments, A3 and A4 are bridged by a single bond or a third bridging group.

[0072] In some embodiments, the second bridging group and the third bridging group are each independently selected from a substituted or unsubstituted linear or branched alkyl group having 1 to 5 carbon atoms, SiR9R 10 , O, S, Se, Te, carbonyl, sulfone, and sulfoxide.

[0073] In some embodiments, R9, R 10 Each occurrence is independently selected from a linear or branched alkyl group having 1 to 5 carbon atoms, and a substituted or unsubstituted aromatic group having 6 to 10 carbon atoms.

[0074] In some embodiments, R9, R 10 Selected from methyl.

[0075] In some embodiments, the second bridging group and the third bridging group are each independently selected from At least one of O, S, Se, Te, carbonyl, sulfone, and sulfoxide.

[0076] In some embodiments, M1 is the same as M2, and Y1 and Y2 are selected from N, which is beneficial to further interrupt the conjugation to weaken the para-electron coupling, which is beneficial to the blue shift of the maximum emission wavelength of the organic compound and reduce the energy loss caused by non-radiative transitions, thereby improving the luminescence performance of the organic compound, enhancing the luminescence efficiency and color purity of the display panel using the organic compound and extending the service life.

[0077] In some embodiments, M1 is the same as M2, A1, A2, A3 and A4 are the same, and X1, X2, X3 and X4 are the same. By selecting A1, A2, A3 and A4 from the same group and X1, X2, X3 and X4 from the same group, the synthesis of the organic compound is facilitated and the manufacturing cost is reduced.

[0078] In some embodiments, when M1 is the same as M2, A1, A2, A3, and A4 are the same, and X1, X2, X3, and X4 are the same, the organic compound has a structure as shown in either Formula (1-1) or Formula (1-2):

[0079] In the general formula (1-1), M1 and M2 are the same and are both selected from B; in the general formula (1-2), M1 and M2 are the same and are both selected from N; in the general formula (1-1) and the general formula (1-2), Y1 and Y2 are the same and are both selected from N.

[0080] In some embodiments, the organic compound is selected from the following compounds:

[0081] 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 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.

[0082] In some embodiments, the lowest unoccupied molecular orbital energy level of the organic compound is greater than or equal to -4.0 eV, and the lowest unoccupied molecular orbital energy level of the organic compound is greater than or equal to -3.0 eV, for example, it can be -3.9 eV, -3.8 eV, -3.7 eV, -3.6 eV, -3.5 eV, -3.4 eV, -3.3 eV, -3.2 eV, -3.1 eV, etc.

[0083] 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 480 nm to 620 nm. The dilute solution of the organic compound can be a solution of the organic compound dissolved in a solvent such as toluene that can dissolve the organic compound to form a concentration of 10 -4 mol / L to 10 -6 mol / L (e.g., 10 -4 mol / L) to obtain a dilute solution.

[0084] 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 20 nanometers, 30 nanometers, 40 nanometers, 50 nanometers, etc., which is beneficial to improving the color purity of the luminescence of the organic compound.

[0085] In some embodiments, the maximum emission peak of the emission spectrum of the dilute solution of the organic compound at room temperature is between 480 nanometers and 580 nanometers. Preferably, the maximum emission peak of the emission spectrum of the dilute solution of the organic compound at room temperature is between 520 nanometers and 575 nanometers, which is conducive to obtaining a green light-emitting material with higher color purity.

[0086] In some embodiments, the fluorescence lifetime of the solid-state thin film formed by the organic compound is between 1 microsecond and 10 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.

[0087] The organic compound with a multiple resonance effect provided by the embodiment of the present invention improves the material properties of the organic compound by lengthening the distance between B and B in the organic compound and / or introducing N to interrupt the conjugation, thereby weakening the para-electron coupling and improving the luminous efficiency and color purity of the display panel using the organic compound and extending the service life.

[0088] Referring to FIG. 1 , the present invention 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.

[0089] 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.

[0090] In some embodiments, the light emitting element 100 can be applied to various electronic devices, such as display panels, lighting devices, light sources, etc.

[0091] 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 .

[0092] 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.

[0093] 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 green light-emitting element, and the light-emitting wavelength of the light-emitting element 100 is within the wavelength range of green light.

[0094] In some embodiments, the host material includes a fused aromatic derivative or a heteroaromatic compound.

[0095] 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.

[0096] 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 99:1 to 70:30, such as 90:10, 85:15, 80:20, 75:25, etc. Preferably, when the light-emitting layer 107 is composed of the host material and the guest material, the mass ratio is 99:1 to 90:10, such as 98:2, 97:3, 96:4, 95:5, 93:7, 92:8, etc. The guest material is dispersed in the host material, and the mass ratio of the host material to the guest material is 99:1 to 70:30, which helps to inhibit crystallization of the light-emitting layer 107 and suppress concentration quenching caused by high concentration of the guest material, thereby improving the luminous efficiency of the light-emitting element 100.

[0097] 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.

[0098] 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.

[0099] In some embodiments, the lowest unoccupied molecular orbital energy level of the sensitizer is greater than or equal to -4.0 eV, and the lowest unoccupied molecular orbital energy level of the sensitizer is greater than or equal to -3.0 eV, for example, it can be -3.9 eV, -3.8 eV, -3.7 eV, -3.6 eV, -3.5 eV, -3.4 eV, -3.3 eV, -3.2 eV, -3.1 eV, etc.

[0100] 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.

[0101] In some embodiments, in the light-emitting layer 107 , the mass ratio of the organic compound, the sensitizer, and the host compound is 1-3:10-30:167-189, for example, 2:20:178.

[0102] 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 480 nanometers and 580 nanometers, and a phosphorescent lifetime of 1 microsecond to 100 milliseconds.

[0103] 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.

[0104] In some embodiments, the sensitizer may be selected from the following compounds:

[0105] 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), 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 invention.

[0106] 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 injecting 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 invention, and the cathode material includes but is 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 cathode material 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.

[0107] 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.

[0108] 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.

[0109] 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.

[0110] 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.

[0111] 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.

[0112] 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.

[0113] Exemplary preparation methods of the organic compounds provided by the present invention are shown in the following exemplary embodiments 1 to 10.

[0114] Example 1

[0115] Organic compound M1 (molecular formula: C 68 H 56 B2N2O4, )

[0116] The synthetic route of organic compound M1 is as follows:

[0117] The specific synthesis steps of organic compound M1 are as follows:

[0118] Synthesis of intermediate 1-a:

[0119] To a 1000 mL two-necked flask were added 2,3,4,6,7,8-hexabromo-1,5-naphthyridine (5.8 g, 10 mmol), 4'-hydroxy-2,4,6-trimethylbiphenyl (8.9 g, 41 mmol), palladium acetate (0.4 g, 2 mmol), tri-tert-butylphosphine tetrafluoroborate (1.8 g, 6 mmol), and lithium tert-butoxide (4.0 g, 50 mmol). Under argon, 400 mL of dry toluene was added. Under argon, the reaction was carried out at 90°C for 24 h. After cooling to room temperature, the reaction solution was poured into 300 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 afford Intermediate 1-a (9.2 g, 82% yield). MS (ESI) (m / z) [M] + :Test value: 1129.2.

[0120] Synthesis of organic compound M1:

[0121] To a 100mL single-necked flask, add intermediate 1-a (3.3g, 3mmol) and ultra-dry o-dichlorobenzene (30mL). Stir at -30°C under anhydrous and oxygen-free conditions for 15 minutes. While maintaining the low temperature, slowly add n-butyllithium (0.21g, 3.0mmol) dropwise, then raise the temperature to 15°C and react for 2 hours. Cool the reaction mixture to -30°C, quickly add boron tribromide (1.50g, 6.0mmol), and heat to 60°C for 3 hours. Then, continue to add N,N-diisopropylethylamine (0.77g, 6.0mmol) while continuing to cool in an ice bath. After the white smoke disappears, raise the temperature to 120°C and react for 1 hour. After the reaction was complete, the mixed solution was cooled to room temperature and methanol was added dropwise under ice bath to quench the reaction. The organic solvent was then dried to obtain a black solid. The solid was extracted three times with dichloromethane and water. The organic phase was collected, concentrated, and purified by column chromatography to obtain organic compound M1 (0.44 g, 15% yield). Elemental analysis (Perkin Elmer 2400, CHN mode) yielded: Calculated: C, 82.77; H, 5.72; N, 2.84; Found: C, 82.24; H, 5.33; N, 2.21; MS (ESI) (m / z) [M] + :Theoretical value: 986.83, tested value: 986.22.

[0122] Example 2

[0123] Organic compound M2 (molecular formula: C 36 H 16 N4O4, )

[0124] The synthetic route of organic compound M2 is as follows:

[0125] The specific synthesis steps of organic compound M2 are as follows:

[0126] Synthesis of intermediate 2-a:

[0127] 3,7-Dibromo-1,5-naphthyridine (2.85 g, 10 mmol), methyl 2-{[2-(methoxycarbonyl)phenyl]amino}benzoate (8.5 g, 30 mmol), Cu powder (0.4 g, 6 mmol), CuI (0.6 g, 3 mmol), potassium carbonate (5.0 g, 36 mmol), and 200 mL of dibutyl ether were added to a 500 mL two-necked flask; the mixture was reacted at 150°C for 48 h under argon protection; the mixture was cooled to room temperature, 300 mL of saturated brine was added, and the mixture was extracted with dichloromethane several times; the organic phases were combined, concentrated, and column chromatography was performed to obtain intermediate 2-a (4.7 g, 72%). MS (ESI) (m / z) [M] + :Test value: 696.76.

[0128] Synthesis of intermediate 2-b:

[0129] 2-a (3.5 g, 5 mmol), sodium hydroxide (2.0 g, 50 mmol), 50 mL of distilled water, and 50 mL of dioxane were added to a 500 mL single-necked flask. The reaction was refluxed at 100°C for 12 h. After cooling to room temperature, concentrated hydrochloric acid was added to a pH of approximately 5.0. The product was then filtered and the filter cake was washed with water to obtain intermediate 2-b (3.0 g, 95%). MS (ESI) (m / z) [M] + :Test value: 640.39.

[0130] Synthesis of organic compound M2:

[0131] In a three-necked flask, intermediate 2-b (2.6 g, 4 mmol) and dichloromethane (80 mL) were added, followed by two drops of DMF and then dropwise addition of thionyl chloride (1.3 mL, 17.6 mmol). The mixture was refluxed at 60°C for 5 h. Aluminum chloride (2.3 g, 17.6 mmol) was then added and refluxed for 12 h. After cooling to room temperature, the reaction solution was added dropwise to 300 mL of 1 M sodium hydroxide solution. The mixture was extracted with dichloromethane, the organic phase was concentrated, and column chromatography afforded the organic compound M2 (1.5 g, 67% yield). Elemental analysis (Perkin Elmer 2400, CHN mode) yielded: Calculated: C, 80.04; H, 3.36; N, 8.49; Found: C, 80.32; H, 3.44; N, 8.21; MS (ESI) (m / z) [M] + :Theoretical value: 568.12, tested value: 568.37.

[0132] Example 3

[0133] Organic compound M3 (molecular formula: C 68 H 52 B2N6, )

[0134] The synthetic route of organic compound M3 is as follows:

[0135] The specific synthesis steps of organic compound M3 are as follows:

[0136] Synthesis of intermediate 3-a:

[0137] Substituting 9,9-dimethyl-9,10-dihydroacridine for 4'-hydroxy-2,4,6-trimethylbiphenyl in Synthesis Example 1-a, the intermediate 3-a (6.8 g, yield 62%) was obtained by the same method. MS (ESI) (m / z) [M] + :Test value: 1117.0.

[0138] Synthesis of organic compound M3:

[0139] Intermediate 3-a (3.3 g, 3 mmol) and ultra-dry o-dichlorobenzene (30 mL) were added to a 100 mL single-necked flask and stirred at -30°C for 15 min under anhydrous and oxygen-free conditions; n-butyllithium (0.21 g, 3.0 mmol) was slowly added dropwise while maintaining the low temperature, and the temperature was raised to 15°C for reaction for 2 h; the temperature was lowered to -30°C, and boron tribromide (1.50 g, 6.0 mmol) was quickly added to the reaction solution, and the temperature was raised to 60°C for reaction for 3 h; then, N,N-diisopropylethylamine (0.77 g, 6.0 mmol) was quickly added under ice bath conditions. After the white smoke disappeared, the temperature was raised to 120°C and the reaction was allowed to react for 1 h; after the reaction was completed, the mixed solution was cooled to room temperature, and methanol was added dropwise under ice bath conditions to quench the reaction, and the organic solvent was then dried to obtain a black solid; the mixture was extracted three times with dichloromethane and water, and the organic phase was collected, concentrated, and subjected to column chromatography to obtain organic compound M3 (0.29 g, yield 10%). Elemental analysis (Perkin Elmer 2400, CHN mode): Calculated: C, 83.78; H, 5.38; N, 8.62; Found: C, 83.46; H, 5.12; N, 8.66; MS (ESI) (m / z) [M] + :Theoretical value: 974.44, tested value: 974.73.

[0140] Example 4

[0141] Organic compound M4 (molecular formula: C 108 H 68 B2N6, )

[0142] The synthetic route of organic compound M4 is as follows:

[0143] The specific synthesis steps of organic compound M4 are as follows:

[0144] Synthesis of intermediate 4-a:

[0145] Substituting 10H-spiro[aza-9,9'-fluorene] for 4'-hydroxy-2,4,6-trimethylbiphenyl in Synthesis Example 1-a, intermediate 4-a (8.5 g, 53% yield) was obtained by the same method. MS (MALDI-TOF) (m / z) [M] + :Test value: 1613.2.

[0146] Synthesis of organic compound M4:

[0147] In a 100 mL single-necked bottle, intermediate 4-a (4.8 g, 3 mmol) and ultra-dry o-dichlorobenzene (30 mL) were added and stirred at -30°C for 15 min under anhydrous and oxygen-free conditions. Keep the temperature low and slowly add n-butyl lithium (0.21 g, 3.0 mmol) dropwise, raise the temperature to 15°C and react for 2 h; cool to -30°C, quickly add boron tribromide (1.50 g, 6.0 mmol) to the reaction solution, raise the temperature to 60°C and react for 3 h; then continue to add N,N-diisopropylethylamine (0.77 g, 6.0 mmol) in an ice bath, wait for the white smoke to disappear, raise the temperature to 120°C and react for 1 h; after the reaction is completed, the mixed solution is cooled to room temperature, methanol is added dropwise in an ice bath to quench the reaction, and the organic solvent is then dried to obtain a black solid; extract with dichloromethane and water three times, collect the organic phase, concentrate the organic phase, and obtain organic compound M4 (0.22 g, yield 5%) by column chromatography, elemental analysis (using Perkin Elmer 2400, CHN mode) Results: Calculated: C, 88.16; H, 4.66; N, 5.71; Measured: C, 88.42; H, 4.48; N, 5.37; MS (ESI) (m / z) [M] + :Theoretical value: 1471.4, tested value: 1471.3.

[0148] Example 5

[0149] Organic compound M5 (molecular formula: C 56 D 28 B2N6, )

[0150] The synthetic route of organic compound M5 is as follows:

[0151] The specific synthesis steps of organic compound M5 are as follows:

[0152] Synthesis of intermediate 5-a:

[0153] Substituting deuterated carbazole for 4'-hydroxy-2,4,6-trimethylbiphenyl in Synthesis Example 1-a, the same method was used to obtain intermediate 5-a (7.0 g, yield 72%). MS (ESI) (m / z) [M] + :Test value: 981.2.

[0154] Synthesis of organic compound M5:

[0155] In a 100 mL single-necked bottle, intermediate 4-a (2.9 g, 3 mmol) and ultra-dry o-dichlorobenzene (30 mL) were added and stirred at -30°C for 15 min under anhydrous and oxygen-free conditions. Keep the temperature low and slowly add n-butyl lithium (0.21 g, 3.0 mmol) dropwise, raise the temperature to 15°C and react for 2 h; cool to -30°C, quickly add boron tribromide (1.50 g, 6.0 mmol) to the reaction solution, raise the temperature to 60°C and react for 3 h; then continue to add N,N-diisopropylethylamine (0.77 g, 6.0 mmol) in an ice bath, wait for the white smoke to disappear, raise the temperature to 120°C and react for 1 h; after the reaction is completed, the mixed solution is cooled to room temperature, methanol is added dropwise in an ice bath to quench the reaction, and the organic solvent is then dried to obtain a black solid; extract with dichloromethane and water three times, collect the organic phase, concentrate the organic phase, and obtain organic compound M5 (0.43 g, yield 17%) by column chromatography, elemental analysis (using Perkin Elmer 2400, CHN mode) Results: Calculated: C, 80.58; H, 6.76; N, 10.07; Measured: C, 80.79; H, 6.99; N, 10.33; MS (ESI) (m / z) [M] + :Theoretical value: 834.67, tested value: 834.33.

[0156] Example 6

[0157] Organic compound M6 (molecular formula: C 44 H 22 B2N4O2, )

[0158] The synthetic route of organic compound M6 is as follows:

[0159] The specific synthesis steps of organic compound M6 are as follows:

[0160] Synthesis of intermediate 6-a:

[0161] 2,6-Dichloro-3,7-dibromo-4,8-diiodo-1,5-naphthyridine (12.2 g, 20 mmol), phenol (4.2 g, 44 mmol), and cesium carbonate (20 g, 60 mmol) were added to a 500 mL two-necked flask; 300 mL of dry DMF was added under argon protection; the reaction was carried out at 90°C under argon protection for 24 h; after cooling to room temperature, the reaction solution was poured into 1 L 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 6-a (11.2 g, 77%). MS (ESI) (m / z) [M] + :Test value: 723.93.

[0162] Synthesis of intermediate 6-b:

[0163] To a 100 mL two-necked flask, add 6-a (7.2 g, 10 mmol), carbazole (8.9 g, 21 mmol), palladium acetate (0.4 g, 2 mmol), tri-tert-butylphosphine tetrafluoroborate (1.8 g, 6 mmol), and lithium tert-butoxide (2.4 g, 30 mmol). Pour 100 mL of dry toluene under argon protection. React at 90°C under argon protection for 24 h. After cooling to room temperature, pour the reaction solution into 300 mL of saturated brine, extract with dichloromethane, wash with saturated brine, and combine the organic phases. Concentrate the organic phase and perform column chromatography to obtain intermediate 1-a (6.3 g, 79% yield). MS (ESI) (m / z) [M] + :Test value: 802.56.

[0164] Synthesis of organic compound M6:

[0165] To a 100mL single-necked flask, add intermediate 6-b (2.4g, 3mmol) and ultra-dry o-dichlorobenzene (30mL). Stir at -30°C under anhydrous and oxygen-free conditions for 15 minutes. While maintaining the low temperature, slowly add n-butyllithium (0.21g, 3.0mmol) dropwise, then raise the temperature to 15°C and react for 2 hours. Cool the reaction mixture to -30°C, quickly add boron tribromide (1.50g, 6.0mmol), and heat it to 60°C for 3 hours. Then, continue to add N,N-diisopropylethylamine (0.77g, 6.0mmol) while continuing to cool the mixture in an ice bath. After the white smoke disappears, raise the temperature to 120°C and react for 1 hour. After the reaction was completed, the mixed solution was cooled to room temperature, and methanol was added dropwise under ice bath to quench the reaction. The organic solvent was then dried to obtain a black solid. The product was extracted three times with dichloromethane and water, and the organic phase was collected and concentrated. The organic phase was purified by column chromatography to obtain organic compound M6 (0.44 g, 22% yield). Elemental analysis (Perkin Elmer 2400, CHN mode) showed the following: theoretical value: C, 80.04; H, 3.36; N, 8.49; found value: C, 80.07; H, 3.30; N, 8.52; MS (ESI) (m / z) [M] + :Theoretical value: 660.31, tested value: 660.37.

[0166] Example 7

[0167] Organic compound M7 (molecular formula: C 40 H 32 N4O4, )

[0168] The synthetic route of organic compound M7 is as follows:

[0169] The specific synthesis steps of organic compound M7 are as follows:

[0170] Synthesis of intermediate 7-a:

[0171] To a 500 mL two-necked flask were added 3,7-dibromo-1,5-naphthyridine (2.85 g, 10 mmol), methyl 2-{[2-(methoxycarbonyl)phenyl]amino}benzoate (2.9 g, 10 mmol), Cu powder (0.2 g, 3 mmol), CuI (0.3 g, 1.5 mmol), potassium carbonate (2.5 g, 18 mmol), and 100 mL of dibutyl ether. The mixture was reacted at 150°C under argon for 48 h. The mixture was cooled to room temperature, 300 mL of saturated brine was added, and the mixture was extracted with dichloromethane several times. The organic phases were combined, concentrated, and purified by column chromatography to yield intermediate 7-a (3.1 g, 63%). MS (ESI) (m / z) [M] + :Test value: 491.07.

[0172] Synthesis of intermediate 7-b:

[0173] 3,7-Dibromo-1,5-naphthyridine (2.85 g, 10 mmol), methyl 2-{[2-(methoxycarbonyl)-4-tert-butylphenyl]amino}benzoate (3.9 g, 10 mmol), Cu powder (0.2 g, 3 mmol), CuI (0.3 g, 1.5 mmol), potassium carbonate (2.5 g, 18 mmol), and 100 mL of dibutyl ether were added to a 500 mL two-necked flask; the mixture was reacted at 150°C under argon protection for 48 h; the mixture was cooled to room temperature, 300 mL of saturated brine was added, and the mixture was extracted with dichloromethane several times; the organic phases were combined, concentrated, and column chromatography was performed to obtain intermediate 7-b (5.7 g, 70%). MS (ESI) (m / z) [M] + :Test value: 808.17.

[0174] Synthesis of intermediate 7-c:

[0175] In a 500 mL single-necked flask, add 7-b (4.0 g, 5 mmol), sodium hydroxide (2.0 g, 50 mmol), 50 mL of distilled water, and 50 mL of dioxane. Reflux at 100°C for 12 h. After cooling to room temperature, add concentrated hydrochloric acid to a pH of approximately 5.0. Filter and wash the filter cake with water to obtain intermediate 7-c (3.7 g, 95%). MS (ESI) (m / z) [M] + :Test value: 752.33.

[0176] Synthesis of organic compound M7:

[0177] In a three-necked flask, intermediate 7-c (3.0 g, 4 mmol) and dichloromethane (80 mL) were added, followed by two drops of DMF and then thionyl chloride (1.3 mL, 17.6 mmol). The mixture was refluxed at 60°C for 5 h. Aluminum chloride (2.3 g, 17.6 mmol) was added and refluxed for 12 h. After cooling to room temperature, the reaction solution was added dropwise to 300 mL of 1 M sodium hydroxide solution. The mixture was extracted with dichloromethane, the organic phase was concentrated, and column chromatography afforded organic compound M7 (1.4 g, 53%). Elemental analysis (Perkin Elmer 2400, CHN mode) yielded the following: Calculated: C, 77.63; H, 4.74; N, 8.23; Found: C, C, 77.66; H, 4.71; N, 8.26; MS (ESI) (m / z) [M] + :Theoretical value: 680.24, tested value: 680.30.

[0178] Example 8

[0179] Organic compound M8 (molecular formula: C 63 H 49 B3N4, )

[0180] The synthetic route of organic compound M8 is as follows:

[0181] The specific synthesis steps of organic compound M8 are as follows:

[0182] Synthesis of intermediate 8-a:

[0183] To a 1000 mL two-necked flask, add 3,5,7-tribromoquinoline (3.6 g, 10 mmol), diphenylamine (5.9 g, 35 mmol), palladium acetate (0.4 g, 2 mmol), tri-tert-butylphosphine tetrafluoroborate (1.8 g, 6 mmol), and sodium tert-butoxide (4.8 g, 50 mmol). Pour 400 mL of dry toluene into the flask under argon protection. The reaction was carried out at 90°C under argon protection for 24 h. After cooling to room temperature, the reaction solution was poured into 300 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 give intermediate 8-a (5.0 g, 80%). MS (ESI) (m / z) [M] + :Test value: 630.33.

[0184] Synthesis of organic compound M8:

[0185] To a 100 mL single-necked flask, intermediate 8-a (1.5 g, 2.3 mmol), triphenylborane (7.3 g, 30 mmol), and ultra-dry o-dichlorobenzene (30 mL) were added. Under anhydrous and oxygen-free conditions, 12 g of boron triiodide was added. The reaction mixture was heated to 180°C and reacted for 8 h. The temperature was then lowered and a THF solution of mesitylene Grignard reagent (24 mL, 28.8 mmol) was added. After stirring at room temperature for 1 h, the mixture was heated to 60°C and stirred for 3 h. The reaction mixture was extracted with toluene and dried over anhydrous magnesium sulfate. Organic compound M8 (0.53 g, 27% yield) was obtained by column chromatography. Elemental analysis (Perkin Elmer 2400, CHN mode) revealed the following: Calculated: C, 84.59; H, 5.52; N, 6.26; Found: C, 84.37; H, 5.35; N, 6.53; MS (ESI) (m / z) [M] + :Theoretical value: 894.42, tested value: 894.22.

[0186] Example 9

[0187] Organic compound M9 (molecular formula: C 78 H 62 B4N6S, )

[0188] The synthetic route of organic compound M9 is as follows:

[0189] The specific synthesis steps of organic compound M9 are as follows:

[0190] Synthesis of intermediate 9-a:

[0191] To a 500 mL two-necked flask, 3,7-dibromo-1,5-naphthyridine (2.85 g, 10 mmol), 7H-dibenzo[c,h]phenothiazine (3.0 g, 10 mmol), palladium acetate (0.4 g, 2 mmol), tri-tert-butylphosphine tetrafluoroborate (1.8 g, 6 mmol), and sodium tert-butoxide (2.4 g, 25 mmol) were added with 200 mL of dry toluene and reacted at 110°C for 48 h under argon. 5-(3-pyridylamino)quinoline (2.2 g, 10 mmol) dissolved in 100 mL of toluene was then added and the reaction continued at 110°C for 48 h. The mixture was cooled to room temperature, 300 mL of saturated brine was added, and the mixture was extracted with dichloromethane several times. The organic phases were combined, concentrated, and purified by column chromatography to yield intermediate 9-a (3.1 g, 48%). MS (ESI) (m / z) [M] + :Test value: 646.33.

[0192] Synthesis of organic compound M9:

[0193] To a 100 mL single-necked flask, intermediate 9-a (1.5 g, 2.3 mmol), triphenylborane (9.7 g, 40 mmol), and ultra-dry o-dichlorobenzene (30 mL) were added. Under anhydrous and oxygen-free conditions, 16 g of boron triiodide was added. The temperature was raised to 180°C and the reaction mixture was reacted for 8 h. The temperature was lowered and a THF solution of mesitylene Grignard reagent (48 mL, 57 mmol) was added. After stirring at room temperature for 1 h, the mixture was heated to 60°C and stirred for 3 h. The reaction mixture was extracted with toluene and dried over anhydrous magnesium sulfate. Organic compound M9 (0.53 g, 20% yield) was obtained by column chromatography. Elemental analysis (Perkin Elmer 2400, CHN mode) revealed the following: Calculated: C, 80.85; H, 5.39; N, 7.25; Found: C, 80.87; H, 5.33; N, 7.29; MS (ESI) (m / z) [M] + :Theoretical value: 1158.5, tested value: 1158.4.

[0194] Example 10

[0195] Organic compound M10 (molecular formula: C 55 H 35 B3N6, )

[0196] The synthetic route of organic compound M10 is as follows:

[0197] The specific synthesis steps of organic compound M10 are as follows:

[0198] Synthesis of organic compound M10:

[0199] To a 100 mL single-necked flask, intermediate 8-a (1.5 g, 2.3 mmol), triphenylborane (7.3 g, 30 mmol) and ultra-dry o-dichlorobenzene (30 mL) were added. Under anhydrous and oxygen-free conditions, 12 g of boron triiodide was added; the temperature was raised to 180°C and the reaction was carried out for 8 h. The room temperature was lowered and a THF solution of 3-pyridyl Grignard reagent (24 mL, 28.8 mmol) was added to the reaction solution; after stirring at room temperature for 1 h, the reaction was heated to 60°C with stirring for 3 h. The reaction solution was extracted with toluene and dried over anhydrous magnesium sulfate. Compound M10 (0.39 g, 22% yield) was obtained by column chromatography. Elemental analysis (Perkin Elmer 2400, CHN mode): Calculated: C, 81.32; H, 4.34; N, 10.35; Found: C, 81.36; H, 4.38; N, 10.27; MS (ESI) (m / z) [M] + :Theoretical value: 812.34, tested value: 812.37.

[0200] Comparative Example 1

[0201] Comparative Compound 1 was used as a comparative example for Examples 1 to 10 above. The structural formulas of Comparative Compound 1 (DABNA-1) and Comparative Compound 2 (R-BN) were:

[0202] The organic compounds M1 to M10 obtained in Examples 1 to 10, and the comparative compounds 1 and 2 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 solution of toluene), the test results are shown in Table 1.

[0203] Table 1: Maximum emission wavelengths (λ) of organic compounds M1 to M10 and comparative compounds 1 and 2 peak ) and full width at half maximum (FWHM)

[0204] As can be seen from the results in Table 1, the maximum emission wavelengths of the organic compounds M1 to M10 provided in Examples 1 to 10 of the present invention are between 525 nm and 562 nm, which are in the green light region compared to the comparative compounds 1 and 2. The half-peak widths of the emission spectra of the organic compounds M1 to M10 are between 22 nm and 34 nm, which have extremely narrow half-peak widths, and are beneficial for use as green light-emitting materials with higher color purity in light-emitting elements.

[0205] The exemplary manufacturing steps of the light-emitting element provided by the present invention are shown in the following exemplary embodiment 11.

[0206] Example 11

[0207] 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 M10 and the comparative compound 3 in Examples 1 to 10 are used as the guest materials in the light-emitting layer of the corresponding light-emitting element, respectively, and Ir(ppy)3 is used as a sensitizer in some light-emitting elements; POT2T 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.

[0208] Specifically, in this embodiment, the above steps were used to obtain light-emitting elements 1 to 20, as well as comparative elements 1 and 2. The guest materials used in light-emitting elements 1 to 10 were organic compounds M1 to M10, respectively, and the guest material used in comparative element 1 was comparative compound 3. Furthermore, the mass ratio of the host material to the guest material in the light-emitting layers of light-emitting elements 1 to 10 and comparative element 1 was 198:2. The guest materials used in light-emitting elements 11 to 20 were organic compounds M1 to M10, respectively, and the guest material used in comparative element 2 was comparative compound 3. Furthermore, the mass ratio of the host material to the sensitizer to the guest material in the light-emitting layers of light-emitting elements 11 to 20 and comparative element 2 was 178:20:2.

[0209] Specifically, HATCN, TAPC, TCTA, mCBP, Ir(ppy)3, POT2T, ANT-BIZ, Liq, and comparative compound 3 (ref-1) are all commercially available. The chemical structures of HATCN, TAPC, TCTA, mCBP, Ir(ppy)3, POT2T, ANT-BIZ, Liq, and comparative compound 3 are as follows:

[0210] In this embodiment, light emitting elements 1 to 20, and comparative elements 1 and 2 were subjected to 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 (CE (cd / A)), 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.

[0211] Table 2: Performance data of Light-emitting Elements 1 to 20 and Comparative Elements 1 and 2

[0212] As shown in Table 2, the light-emitting elements 1 to 10 obtained by using guest materials M1 to M10 in the light-emitting layer of the present invention have significantly improved luminous efficiency compared to the comparative element 1 under the condition of equivalent driving voltage, and the light-emitting elements 11 to 20 also have significantly improved luminous efficiency compared to the comparative element 2 under the condition of equivalent driving voltage; further, the luminous efficiency of the light-emitting elements 1 to 10 are all in the range of 55.3 cd / A to 67.3 cd / A, and the luminous efficiency of the light-emitting elements 11 to 20 are all in the range of 102 cd / A to 138 cd / A, indicating that the addition of the sensitizer effectively improves the luminescence efficiency. The luminous efficiency of the element is improved; at the same time, the time taken for the brightness of light-emitting elements 3 to 5 and light-emitting elements 7 to 9 to decrease from the same initial brightness to 95% of the initial brightness is all within the range of 72h to 95h, which is significantly improved compared with the time taken for the brightness of comparative element 1 to decrease from the same initial brightness to 95% of the initial brightness; the time taken for the brightness of light-emitting elements 13 to 19 to decrease from the same initial brightness to 95% of the initial brightness is all within the range of 78h to 85h, which is significantly improved compared with the time taken for the brightness of comparative element 2 to decrease from the same initial brightness to 95% of the initial brightness. In addition, the time taken for the brightness of light-emitting elements 11 to 20 to decrease from the same initial brightness to 95% of the initial brightness is significantly increased compared with light-emitting elements 1 to 10 when using the same guest material, indicating that the addition of the sensitizer is beneficial to stabilizing the light-emitting element and extending the life of the light-emitting element.

[0213] The light-emitting element disclosed in the embodiment of the present invention uses the organic compound with a multiple resonance effect, and weakens the para-electron coupling by lengthening the distance between B and B in the organic compound and / or introducing N to interrupt the conjugation, thereby improving the material properties of the organic compound, thereby improving the luminous efficiency and color purity of the display panel using the organic compound and extending the service life.

[0214] Referring to FIG. 2 , an embodiment of the present invention further discloses a display panel 10 , which includes any of the above-mentioned light-emitting elements 100 .

[0215] In some embodiments, the display panel 10 further includes an array substrate 200 located on one side of the light emitting element 100 .

[0216] The array substrate 200 includes a substrate 210 , and the light emitting element 100 is disposed on one side of the substrate 210 .

[0217] 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.

[0218] In some embodiments, the light emitting element 100 is a green light emitting element G, and the display panel 10 further includes a red light emitting element R and a blue light emitting element B.

[0219] 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.

[0220] 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 .

[0221] 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.

[0222] The display panel disclosed in the embodiment of the present invention uses an organic compound with a multiple resonance effect in the light-emitting element, and weakens the para-electron coupling by lengthening the distance between B and B in the organic compound and / or introducing N to interrupt the conjugation, thereby improving the material properties of the organic compound, thereby improving the luminous efficiency and color purity of the display panel using the organic compound and extending the service life.

[0223] The embodiment of the present invention discloses an organic compound and a display panel. The organic compound has a structure as shown in general formula (1): The present invention improves the material properties of the organic compound by using an organic compound with a multiple resonance effect and by lengthening the distance between B and B in the organic compound and / or introducing N to interrupt the conjugation to weaken the para-electron coupling, thereby enhancing the luminous efficiency and color purity of the display panel using the organic compound and extending the service life.

[0224] It is understandable that those skilled in the art can make equivalent substitutions or changes based on the technical solution and inventive concept of this application, and all these changes or substitutions should fall within the scope of protection of the claims attached to this application.

Claims

1. An organic compound, wherein, The organic compound has a structure represented by the general formula (1): Wherein, M1 and M2 are each independently selected from B and N; Y1 and Y2 are each independently selected from C and N, and at least one of Y1 and Y2 is selected from N; A1, A2, A3, and A4 are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, A1 and A2 may or may not form a ring with each other, and A3 and A4 may or may not form a ring with each other; When M1 is selected from B, X1 and X2 are each independently selected from electron-donating groups; When M1 is selected from N, X1 and X2 are each independently selected from electron-withdrawing groups; When M2 is selected from B, X3 and X4 are each independently selected from electron-donating groups; When M2 is selected from N, X3 and X4 are each independently selected from electron-withdrawing groups.

2. The organic compound according to claim 1, wherein, When M1 is selected from B, X1 and X2 are each independently selected from at least one of N-R1, O, and S; When M1 is selected from N, X1 and X2 are each independently selected from at least one of B-R1, carbonyl group, sulfone group, and sulfoxide group; When M2 is selected from B, X3 and X4 are each independently selected from at least one of N-R1, O, and S; When M2 is selected from N, X3 and X4 are each independently selected from at least one of B-R1, carbonyl group, sulfone group, and sulfoxide group; Wherein, each occurrence of R1 is independently selected from H, D, T, a substituted or unsubstituted straight-chain alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted branched-chain alkyl group or cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 15 carbon atoms.

3. The organic compound according to claim 2, wherein, At least one of A1 to A4 adjacent to R1 is bridged to R1 by a single bond or a first bridging group; Wherein, each occurrence of the first bridging group is independently selected from at least one of N-R2, CR3R4, SiR5R6, O, S, Se, Te, carbonyl group, sulfone group, and sulfoxide group; Each occurrence of R2, R3, R4, R5, and R6 is independently selected from H, D, T, a substituted or unsubstituted straight-chain alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted branched-chain alkyl group or cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 15 carbon atoms.

4. The organic compound according to claim 3, wherein, Each occurrence of the first bridging group is independently selected from at least one of the groups such as O, S, Se, Te, carbonyl group, sulfone group, sulfoxide group, etc.

5. The organic compound according to claim 1, wherein, M1 and M2 are the same, and Y1 and Y2 are selected from N.

6. The organic compound according to claim 5, wherein, A1, A2, A3, and A4 are the same, and X1, X2, X3, and X4 are the same.

7. The organic compound according to claim 6, wherein, The organic compound has a structure represented by any one of general formula (1-1) or general formula (1-2):

8. The organic compound according to claim 1, wherein, A1, A2, A3, and A4 are each independently selected from a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms.

9. The organic compound according to claim 1, wherein, A1 and A2 are bridged by a single bond or a second bridging group, and A3 and A4 are bridged by a single bond or a third bridging group; Wherein, each occurrence of the second bridging group and the third bridging group is independently selected from at least one of a substituted or unsubstituted straight-chain alkyl or branched-chain alkyl having 1 to 5 carbon atoms, SiR9R 10 , O, S, Se, Te, carbonyl, sulfone, sulfoxide; R9, R 10 Each occurrence is independently selected from a straight-chain alkyl or branched-chain alkyl having 1 to 5 carbon atoms, and a substituted or unsubstituted aromatic group having 6 to 10 carbon atoms.

10. The organic compound according to claim 9, wherein, R9, R 10 Selected from methyl.

11. The organic compound according to claim 10, wherein, Each occurrence of the second bridging group and the third bridging group is independently selected from at least one of O, S, Se, Te, carbonyl, sulfone, and sulfoxide.

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 greater than or equal to -5.0 eV; The lowest unoccupied molecular orbital energy level of the organic compound is greater than or equal to -4.0 eV, and the lowest unoccupied molecular orbital energy level of the organic compound is greater than or equal to -3.0 eV.

14. A display panel, wherein, Comprising: A substrate; A first electrode layer disposed 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; Among them, the material of the organic functional layer includes an organic compound, and the organic compound has a structure represented by the general formula (1): Wherein, M1 and M2 are each independently selected from B and N; Y1 and Y2 are each independently selected from C and N, and at least one of Y1 and Y2 is selected from N; A1, A2, A3, and A4 are each independently selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, A1 and A2 may or may not form a ring with each other, and A3 and A4 may or may not form a ring with each other; When M1 is selected from B, X1 and X2 are each independently selected from at least one of an electron-donating group; When M1 is selected from N, X1 and X2 are each independently selected from at least one of an electron-withdrawing group; When M2 is selected from B, X3 and X4 are each independently selected from at least one of an electron-donating group; When M2 is selected from N, X3 and X4 are each independently selected from at least one of an electron-withdrawing group.

15. The display panel according to claim 14, wherein, The organic functional layer at least includes a light-emitting layer, the light-emitting layer includes a host material and a guest material, and the guest material is one or more of the organic compounds.

16. The display panel according to claim 14, wherein, The organic functional layer at least includes a light-emitting layer, the light-emitting layer includes a host material, a guest material, and a sensitizer, the guest material is one or more of the organic compounds, and the sensitizer is at least one of a phosphorescent material and a thermally activated delayed fluorescence material.

17. The display panel according to claim 14, wherein, When M1 is selected from B, X1 and X2 are each independently selected from at least one of N-R1, O, and S; When M1 is selected from N, X1 and X2 are each independently selected from at least one of B-R1, a carbonyl group, a sulfone group, and a sulfoxide group Among them; When M2 is selected from B, X3 and X4 are each independently selected from at least one of N-R1, O, and S; When M2 is selected from N, X3 and X4 are each independently selected from at least one of B-R1, a carbonyl group, a sulfone group, and a sulfoxide group; Wherein, each occurrence of R1 is independently selected from H, D, T, a substituted or unsubstituted straight-chain alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted branched-chain alkyl group or cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 15 carbon atoms.

18. The display panel according to claim 17, wherein, At least one of A1 to A4 adjacent to R1 is bridged to R1 by a single bond or a first bridging group; Wherein, each occurrence of the first bridging group is independently selected from at least one of N-R2, CR3R4, SiR5R6, O, S, Se, Te, a carbonyl group, a sulfone group, and a sulfoxide group; Each occurrence of R2, R3, R4, R5, and R6 is independently selected from H, D, T, a substituted or unsubstituted straight-chain alkyl group having 1 to 5 carbon atoms, a substituted or unsubstituted branched alkyl or cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aromatic group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaromatic group having 5 to 15 carbon atoms.

19. The display panel according to claim 14, wherein, M1 is the same as M2, and Y1 and Y2 are selected from N.

20. The display panel according to claim 19, wherein, A1, A2, A3, and A4 are the same, and X1, X2, X3, and X4 are the same.

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