Compound, electroluminescent device and display panel

Abstract

A compound, an electroluminescent device and a display panel. The compound has a structural general formula.

Description

Compound, electroluminescent device and display panel

[0001] This application claims priority to the Chinese patent application No. 202410474464.X, filed on April 18, 2024, to the Chinese Patent Office, the content of which is incorporated herein by reference in its entirety. TECHNICAL FIELD

[0002] The present application relates to the technical field of organic optoelectronic materials, in particular to a compound, an electroluminescent device and a display panel. BACKGROUND

[0003] Organic light-emitting diode (OLED) has a broad application prospect in the field of flexible display and solid-state lighting due to its advantages of self-luminescence, high contrast, wide viewing angle, high luminous efficiency, fast response, lightness, foldability and the like. The core of OLED is guest light-emitting material. The guest light-emitting material has developed from the traditional fluorescent material to the phosphorescent material, and then to the thermally activated delayed fluorescence (TADF) material in recent years, which has experienced three generations of replacement. The ratio of singlet and triplet excitons formed under the electrically induced condition of OLED is 1:3, so the theoretical internal quantum efficiency (IQE) of OLED based on fluorescent material can only reach 25%. The spin-orbit coupling effect of heavy metal atoms in phosphorescent material can achieve 100% IQE, but the use of iridium (Ir), platinum (Pt) and other heavy metals will pollute the environment and increase the cost, in addition, the long-life phosphorescent material for deep blue light still needs to be improved in both academic and industrial fields. TADF material can achieve 100% exciton utilization rate through the reverse intersystem crossing (RISC) process, but the intramolecular charge transfer effect makes its spectrum wide, although the emergence of boron-nitrogen materials greatly improves this situation, but this problem under the electrically induced condition cannot be ignored, in addition, the thermal stability of multi-boron materials will also limit their commercial application.

[0004] In order to solve the problems of the above-mentioned materials, the "superfluorescent" strategy is proposed in the industry, that is, a small amount of TADF material or phosphorescent material is doped to sensitize the traditional fluorescent material with a narrow spectral band, so that the long lifetime advantage of the traditional fluorescent material can be maintained, and narrow spectrum emission and 100% exciton utilization can be realized at the same time. At present, the narrow spectrum fluorescent material emits blue light in most cases due to the limitation of its molecular skeleton, and the narrow spectrum fluorescent material of other colors has not been fully developed. Therefore, the narrow emission fluorescent material of other colors (such as green light and red light) with high efficiency and long lifetime needs to be developed. Technical solutions

[0005] Embodiments of the present application provide a compound, an electroluminescent device and a display panel to solve the problems of single light color and spectrum of existing fluorescent materials.

[0006] To solve the above problems, the technical solutions provided by the present application are as follows:

[0007] Embodiments of the present application provide a compound, the structure of the compound is as shown in formula (I):

[0008] wherein A1, A2 and A3 are independently selected from substituted or unsubstituted aromatic groups with 6-50 carbon atoms;

[0009] X1 and X3 are independently selected from non-bonding, single bond, carbonyl, sulfone, isopropyl or substituted or unsubstituted arylalkyl with 6-50 carbon atoms, and at most one of X1 and X3 is selected from non-bonding;

[0010] X2 is selected from substituted or unsubstituted alkyl with 3-30 carbon atoms, substituted or unsubstituted arylalkyl with 6-50 carbon atoms, substituted or unsubstituted arylsilane with 6-50 carbon atoms, substituted or unsubstituted arylamine with 6-50 carbon atoms, oxygen atom, sulfur atom, selenium atom, carbonyl, sulfone or sulfoxide, when X2 contains at least one benzene ring, A1 and the adjacent benzene ring are ringed or not ringed, A2 and the adjacent benzene ring are ringed or not ringed.

[0011] Embodiments of the present application also provide an electroluminescent device, which comprises an anode and a cathode, and a light-emitting layer between the anode and the cathode, the light-emitting layer comprising at least one functional material and a compound;

[0012] The structure of the compound is as shown in formula (I):

[0013] wherein A1, A2 and A3 are independently selected from substituted or unsubstituted aromatic groups with 6-50 carbon atoms;

[0014] X1and X3are independently of each other selected from the group consisting of a single bond, a carbonyl group, a sulfone group, an isopropyl group, or a substituted or unsubstituted arylalkyl group having 6 to 50 carbon atoms, and at most one of X1and X3is selected from a single bond;

[0015] X2is selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 50 carbon atoms, an oxygen atom, a sulfur atom, a selenium atom, a carbonyl group, a sulfone group, or a sulfoxide group, and when X2contains at least one benzene ring, A1forms a ring or does not form a ring with an adjacent one of the benzene rings, and A2forms a ring or does not form a ring with an adjacent one of the benzene rings.

[0016] The embodiments of the present application also provide a display panel comprising the compound, and a structure general formula of the compound is shown as formula (I):

[0017] wherein A1, A2, and A3are independently of each other selected from the group consisting of a substituted or unsubstituted aromatic group having 6 to 50 carbon atoms;

[0018] X1and X3are independently of each other selected from the group consisting of a single bond, a carbonyl group, a sulfone group, an isopropyl group, or a substituted or unsubstituted arylalkyl group having 6 to 50 carbon atoms, and at most one of X1and X3is selected from a single bond;

[0019] X2is selected from the group consisting of a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 50 carbon atoms, an oxygen atom, a sulfur atom, a selenium atom, a carbonyl group, a sulfone group, or a sulfoxide group, and when X2contains at least one benzene ring, A1forms a ring or does not form a ring with an adjacent one of the benzene rings, and A2forms a ring or does not form a ring with an adjacent one of the benzene rings.

[0020] Alternatively, the display panel comprises an electroluminescent device, the electroluminescent device comprises an anode and a cathode, and a light-emitting layer between the anode and the cathode, the light-emitting layer comprises at least one functional material and the compound. BRIEF DESCRIPTION OF DRAWINGS

[0021] FIG. 1 is a fluorescence spectrum of a target compound synthesized by embodiments 1-10 of the present application and compound A in a toluene solution.

[0022] FIG. 2 is a schematic diagram of a film layer stack of an electroluminescent device provided by embodiments of the present application. EMBODIMENTS OF THE INVENTION

[0023] The present application provides a compound, an electroluminescent device and a display panel. In order to make the purpose, technical solutions and effects of the present application clearer and more explicit, the present application is further described in detail below. It should be understood that the specific embodiments described herein are only used to explain the present application and are not intended to limit the present application.

[0024] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. The terminology used in the description herein is for describing particular embodiments only and is not intended to be limiting of the application. In the present application, "substituted" means that a hydrogen atom in a substituent is replaced by a substituent; "unbonded" means that the structural unit does not exist.

[0025] In the present application, "substituted or unsubstituted" means that the defined group can be substituted or unsubstituted. When the defined group is substituted, it is understood that the defined group can be substituted with one or more substituents R selected from, but not limited to, deuterium, tritium, cyano, isocyano, nitro or halogen, alkyl containing 1-20 carbon atoms, heterocyclyl containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halogenformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above-mentioned groups can also be further substituted with an acceptable substituent in the art; it is understood that R' and R" in -NR'R" are independently selected from, but not limited to, H, deuterium, tritium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclyl containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms. Preferably, R is selected from, but not limited to, deuterium, tritium, cyano, isocyano, nitro, halogen, alkyl containing 1-10 carbon atoms, heterocyclyl containing 3-10 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, silyl, carbonyl, alkoxycarbonyl, aryloxycarbonyl, carbamoyl, halogenformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above-mentioned groups can also be further substituted with an acceptable substituent in the art. More preferably, R is selected from, but not limited to, deuterium, tritium, cyano, nitro, carbonyl, sulfone or halogen.

[0026] In the present application, when the substitution or unsubstitution of a group is not emphasized, it is by default that the group is unsubstituted. For example, "alkyl with carbon atom number 3-30" refers to unsubstituted alkyl with carbon atom number 3-30.

[0027] In the present application, the number of atoms described by a numerical range includes both integer endpoints of the numerical range, and also includes each integer in the two endpoints. For example, "1-10 carbon atoms" means 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms.

[0028] In the present application, "halogen" or "halogen atom" refers to F, Cl, Br, or I.

[0029] In the present application, an "aromatic group" can be considered as an aromatic group if it satisfies the following three conditions: ① a closed ring conjugated system; ② satisfies the 4n+2 Hückel rule, n is 0 or a positive integer; ③ all atoms in the ring are coplanar. The "aromatic group" has no requirement on the type of atoms in the ring, and in addition to carbon atoms, the atoms in the ring can also include Si, N, P, O, S and other heteroatoms. "Aryl" or "aromatic group" refers to an aromatic hydrocarbon group derived by removing a hydrogen atom from an aromatic ring compound, which can be a monocyclic aryl group, or a fused ring aryl group, or a polycyclic aryl group. Suitable examples include but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthene, triphenylene, pyrene, perylene, naphthacene, fluorene, rylene, acenaphthene, and derivatives thereof.

[0030] The structural general formula of the compound provided in the embodiments of the present application is shown as formula (I):

[0031] Among them, A1, A2 and A3 can be independently selected from substituted or unsubstituted aromatic groups with 6-50 carbon atoms.

[0032] X1 and X3 can be independently selected from non-bonding, single bond, carbonyl, sulfone group, isopropyl, or substituted or unsubstituted arylalkyl with 6-50 carbon atoms, and at most one of X1 and X3 is selected from non-bonding.

[0033] X2 can be selected from substituted or unsubstituted alkyl with 3-30 carbon atoms, substituted or unsubstituted arylalkyl with 6-50 carbon atoms, substituted or unsubstituted arylsilane with 6-50 carbon atoms, substituted or unsubstituted arylamine with 6-50 carbon atoms, oxygen atom, sulfur atom, selenium atom, carbonyl, sulfone group or sulfoxide group.

[0034] When X2 contains at least one benzene ring, A1 can be ringed or not ringed with the adjacent benzene ring in X2, and A2 can be ringed or not ringed with the adjacent benzene ring in X2.

[0035] The compound shown in the above formula (I) is a central symmetric structure, and the vibration spectrum of the molecule in the central symmetric type is narrower, and the above molecular design is beneficial to narrow the spectrum of the fluorescent material.

[0036] The above compound provided in the embodiments of the present application has a fluorescence spectrum in the range of 400-700 nm at 10-5 The compound has a half-peak width of emission spectrum in a 10-3 mol / L toluene solution of less than 50 nm, and a peak value between 450 nm and 550 nm, showing blue or green light emission. The compound can be used as a luminescent material of a fluorescent material type, whether in a solid-state thin film or in a solution, and the absolute photoluminescence quantum yield of the compound with the narrow spectrum can reach more than 90%.

[0037] The compound provided in the embodiments has good thermal stability, and the glass transition temperature Tg can reach 100 DEG C or above, the decomposition temperature Td at which the mass loss is 1% can reach 350 DEG C or above, the energy level of the highest occupied orbital (HOMO) can reach-5.7 eV or above, and the energy level of the lowest unoccupied orbital (LUMO) can reach-2.9 eV or below.

[0038] The present application expands the conjugated system of the central fused ring of the compound, and introduces a group with electron-withdrawing properties and capable of forming a multiple resonance effect, so as to reduce the vibration of the molecule, narrow the spectrum, and control the light color, thereby improving the luminescent performance of the compound as a fluorescent material. The compound can be used as a luminescent material in an organic electroluminescent device, and compared with the existing materials, the compound applied in the electroluminescent device can achieve a narrower luminescent spectrum, a lower working voltage, a higher luminescent efficiency and a longer service life.

[0039] In the present application, when X2 is selected from a substituted or unsubstituted arylalkyl group with 6-50 carbon atoms, a substituted or unsubstituted arylsilyl group with 6-50 carbon atoms, etc., the bond connection site is on the alkyl group.

[0040] In some embodiments, A3 can be selected from a substituted or unsubstituted anthracene, phenazine, phenanthrene, phenanthroline, pyrene, perylene.

[0041] In some embodiments, the compound is selected from at least one of the compounds shown in the following formula (I-1) to (I-2):

[0042] wherein the groups of X1 to X3, A1, A2 are selected in the same manner as the selection of the general formula (I), that is, A1 and A2 are independently selected from a substituted or unsubstituted aromatic group with 6-30 carbon atoms.

[0043] In the embodiments of the present application, Y1, Y2, Y3 and Y4 can be independently selected from C or N.

[0044] Alternatively, in some embodiments, Y1 and Y2 are the same, and further can be selected from C or N; Y3 and Y4 are the same, and further can be selected from C or N. In this way, the central symmetric structure of the molecule is enhanced, which is beneficial to narrow the luminescent spectrum.

[0045] R1, R2, R3, and R4may be independently selected from hydrogen, deuterium, tritium, cyano, nitro, carbonyl, sulfone, halogen atom, substituted or unsubstituted linear alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, substituted or unsubstituted cyclic alkyl group having 3 to 20 carbon atoms, substituted or unsubstituted silyl group having 1 to 20 carbon atoms, and substituted or unsubstituted aromatic group having 6 to 50 carbon atoms.

[0046] In some embodiments, R3and R4may or can not be cyclic.

[0047] Optionally, R1, R2, R3, and R4may be independently selected from hydrogen, deuterium, tritium, cyano, nitro, carbonyl, sulfone, halogen atom, linear alkyl group having 1 to 10 carbon atoms, branched alkyl group having 1 to 10 carbon atoms, cyclic alkyl group having 1 to 10 carbon atoms, and silyl group having 1 to 10 carbon atoms. Optionally, R3and R4may not be cyclic.

[0048] In some embodiments, R1, R2, R3, and R4may be independently selected from hydrogen, deuterium, tritium, cyano, nitro, carbonyl, sulfone, halogen atom, linear alkyl group having 1 to 10 carbon atoms, branched alkyl group having 3 to 10 carbon atoms, cyclic alkyl group having 3 to 10 carbon atoms, and silyl group having 1 to 10 carbon atoms, and R3and R4may not be cyclic.

[0049] Further, in some embodiments, A1and A2may be independently selected from substituted or unsubstituted aromatic group having 6 to 30 carbon atoms.

[0050] Optionally, A1and A2may be independently selected from substituted or unsubstituted phenyl group. Further, when the phenyl group is substituted, it can be substituted with deuterium, tritium, halogen, cyano, nitro, carbonyl, sulfone, linear alkyl group having 1 to 10 carbon atoms, branched alkyl group having 1 to 10 carbon atoms, cyclic alkyl group having 1 to 10 carbon atoms, and the like.

[0051] Further, in some embodiments, X1and X3may be independently selected from non-bonding, single bond, carbonyl, sulfone, isopropyl group, or arylalkyl group having 7 to 30 carbon atoms, and at most one of X1and X3is selected from non-bonding. Optionally, the arylalkyl group can have 7 to 20 carbon atoms.

[0052] Further, in some embodiments, X2may be selected from the group consisting of substituted or unsubstituted alkyl having 3 to 30 carbon atoms, substituted or unsubstituted arylalkyl having 6 to 30 carbon atoms, substituted or unsubstituted arylsilyl having 6 to 30 carbon atoms, substituted or unsubstituted arylamine having 6 to 30 carbon atoms, oxygen atom, sulfur atom, selenium atom, carbonyl group, sulfone group, or sulfoxide group. When X2contains at least one benzene ring, A1may or can not be annulated with the adjacent benzene ring, and A2may or can not be annulated with the adjacent benzene ring.

[0053] In some embodiments, when X2is selected from the group consisting of the substituted or unsubstituted arylamine having 6 to 50 carbon atoms, A1is annulated with the adjacent benzene ring in X2, and A2is not annulated with the adjacent benzene ring in X2; when X2is selected from the group consisting of the substituted or unsubstituted arylalkyl having 6 to 50 carbon atoms, A1is not annulated with the adjacent benzene ring in X2, and A2may or can not be annulated with the adjacent benzene ring in X2.

[0054] Specifically, the compound can be selected from at least one of the compounds represented by the following structural formulae I-1-1 to I-1-129, I-2-1 to I-2-96:

[0055] Based on the above-mentioned compound, an embodiment of the present application further provides an electroluminescent device, which comprises an anode and a cathode, and a light-emitting layer between the anode and the cathode. The light-emitting layer comprises at least one functional material and the compound in the above-mentioned embodiment. The functional material can comprise a host light-emitting material, and a first guest light-emitting material. The first guest light-emitting material can be a phosphorescent material, as a sensitizer. The functional material can further comprise a second guest light-emitting material, and the above-mentioned compound can be used as another guest light-emitting material (i.e. the second guest light-emitting material) of the light-emitting layer.

[0056] In some embodiments, the electroluminescent device can further comprise a hole injection layer, a hole transport layer, and an electron blocking layer, which are sequentially stacked on the anode and between the anode and the light-emitting layer.

[0057] In some embodiments, the electroluminescent device can further comprise a hole blocking layer, an electron transport layer, and an electron injection layer, which are sequentially stacked on the light-emitting layer and between the light-emitting layer and the cathode.

[0058] The electroluminescent device according to the present application can be selected from, but not limited to, an organic light emitting diode (OLED), an organic photovoltaic cell, an organic luminescent cell, an organic field effect transistor, an organic light emitting field effect transistor, an organic laser, an organic spintronics device, an organic sensor, and an organic plasmonic emission diode, and is particularly preferred to be an OLED.

[0059] In embodiments of the present application, the anode can comprise a conductive metal, a metal oxide, or a conductive polymer. The anode can readily inject holes into a hole injection layer, a hole transport layer, or an emission layer.

[0060] In some embodiments, examples of anode materials include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like. Other anode materials are known and can be readily selected for use by one of ordinary skill in the art. The anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, e-beam, and the like.

[0061] In some embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to fabricate electroluminescent devices according to the present application.

[0062] In the present application, the cathode can comprise a conductive metal or a metal oxide. The cathode can readily inject electrons into an electron injection layer or an electron transport layer or directly into an emission layer.

[0063] In principle, all materials that can be used as a cathode for an OLED can be used as a cathode material for the devices of the present application. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like. 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, e-beam, and the like.

[0064] The hole injection material, the hole transport material, the hole blocking material, the electron blocking material, the electron transport material, and the electron injection material used in the electroluminescent device of the present application are not particularly limited, and any compound can be used as long as the compound is generally used as a hole injection material, a hole transport material, an electron blocking material, an electron transport material, and an electron injection material.

[0065] The application also provides a display panel, which can be a rigid display panel or a flexible display panel. The display panel comprises the electroluminescent device of any one of the above embodiments or the compound of any one of the above embodiments. The display panel can further comprise a pixel driving circuit for driving the light-emitting layer to emit light, and the pixel driving circuit includes but is not limited to a thin film transistor driving circuit.

[0066] The application also relates to the use of the electroluminescent device according to the application in various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, X-ray scintillators, biological imaging, and the like. The display devices include, for example, but are not limited to, mobile phones, vehicle-mounted display screens, AR, VR, notebook computers, televisions, and the like.

[0067] DETAILED DESCRIPTION

[0068] The application will be described in detail below through specific embodiments. The following embodiments are only part of the embodiments of the application and are not limiting of the application. The raw materials used in the following embodiments are commercially available products, unless otherwise specified. Among them, DMAC: N,N-dimethylacetamide; DCM: dichloromethane; Pd(OAc)2: palladium acetate; DMF: N,N-dimethylformamide; SnCl2: stannous chloride.

[0069] Embodiment 1

[0070] The synthesis route of the target compound I-1-1 of this embodiment is as follows:

[0071] Synthesis steps:

[0072] 1.1 Synthesis of intermediate 1-a: under anhydrous and anaerobic conditions, 2,6-dibromoanthracene (3.33 g, 10.0 mmol), DMAC (4.18 g, 20.0 mmol), palladium acetate (0.24 g, 1.0 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.6 g, 2.0 mmol) and sodium tert-butoxide (3.84 g, 40 mmol) were added to a 500 ml reaction bottle, and the resulting mixture was dissolved in 100 mL of toluene after being distilled, heated to 110°C, and reacted overnight. After the reaction was completed, the reaction liquid was cooled, extracted with DCM and water three times, and the organic phases were combined. A small amount of saturated brine was added to the organic phase, then dried with anhydrous sodium sulfate, and the organic solvent was removed by rotary evaporation. Finally, column chromatography was performed using petroleum ether / ethyl acetate (volume ratio 10:1) as the eluent to obtain intermediate 1-a as a yellow powder solid (5.03 g, 0.85 mmol), with a yield of 85%. MS (EI) m / z: [M] + 592.29.

[0073] 1.2 Synthesis of target compound I-1-1: A mixture of intermediate 1-a (1.06 g, 2.0 mmol), Pd(OAc)2(0.27 g, 1.2 mmol), silver oxide (1.38 g, 0.60 mmol), tri-tert-butylphosphonium tetrafluoroborate (1.15 g, 12 mmol), pivalic acid (15 mL) and K2CO3(3.90 g, 12.0 mmol) was added to a 100 mL reaction flask, and refluxed under argon for 2 h, cooled to room temperature, then neutralized with saturated NaHCO3solution, and the reaction mixture was extracted with brine and DCM. The collected organic phase was dried, and purified by column chromatography on silica gel with DCM / petroleum ether (volume ratio 15:1) as eluent to give target compound I-1-1 (0.47 mg, 0.8 mmol). The yield was 40%. MS (EI) m / z: [M]+ + 588.26.

[0074] Example 2

[0075] The synthetic route of target compound I-1-2 of this example is as follows:

[0076] Synthetic steps:

[0077] 2.1 Synthesis of intermediate 2-a: Under anhydrous and anaerobic conditions, a mixture of 2,6-dibromoanthracene (3.39 g, 10.0 mmol), aniline (1.87 g, 20.0 mmol), palladium acetate (0.24 g, 1.0 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.6 g, 2.0 mmol) and sodium tert-butoxide (3.84 g, 40 mmol) was dissolved in 100 mL of toluene, and the solution was heated to 110 °C overnight. After the reaction was completed, the reaction solution was cooled, extracted with DCM and water three times, and the organic phases were combined. A small amount of saturated brine was added to the organic phase, which was then dried with anhydrous sodium sulfate, and the organic solvent was removed by rotary evaporation. Finally, column chromatography was performed using petroleum ether / DCM (volume ratio 4:1) as eluent to give intermediate 2-a as a white powder solid (5.04 g, 0.70 mmol) with a yield of 70%. MS (EI) m / z: [M]+ + 360.16.

[0078] 2.2 Synthesis of intermediate 2-b: Anhydrous and oxygen-free conditions, a 250 mL Schlenk flask was charged with intermediate 2-a (1.8 g, 5.0 mmol), dimethyl 2-bromoisophthalate (2.72 g, 10.0 mmol), potassium carbonate (2.07 g, 15.0 mmol), CuI (0.1 g, 0.5 mmol), Cu / Sn (0.2 g, 1.0 mmol), 2,2,6,6-tetramethyl-3,5-heptanedione (0.11 g, 0.5 mmol) and 30 mL of anhydrous dibutyl ether. The mixture was heated at 150 °C for 3 days. After the reaction was completed, the mixture was cooled to room temperature, and then DCM (100 mL) was added to the mixture, and the mixture was washed with saturated aqueous sodium chloride solution (100 mL) for 3 times. The collected organic phase was dried over anhydrous sodium sulfate, and the organic solvent was removed by rotary evaporation; finally, column chromatography was performed using petroleum ether / ethyl acetate (volume ratio 1:4) as the eluent to obtain intermediate 2-b as a yellow powder solid (2.42 g, 0.65 mmol) with a yield of 65%. MS (EI) m / z: [M]+ + 744.25.

[0079] 2.3 Synthesis of target compound I-1-2: A 100 mL reactor was charged with intermediate 2-b (2.23 g, 3 mmol), sodium hydroxide (1.21 g, 30 mmol) and 20 mL of a mixture of ethanol / water (1:1). The reaction was heated to reflux for 12 hours. After the reaction was cooled to room temperature, dilute hydrochloric acid was added to adjust the pH value to 2-3. The diacid precipitated as a light green solid after hydrolysis, which was collected by vacuum filtration, washed thoroughly with water, and dried under vacuum for use without further purification and characterization. Anhydrous and oxygen-free conditions, the diacid solid (0.59 g, 0.87 mmol) was dissolved in 20 mL of dichloromethane solution under nitrogen atmosphere. Thionyl chloride (0.16 mL, 2.16 mmol) and 3 drops of DMF were added to the reaction system in turn. After refluxing for 3 hours, the reaction mixture was cooled to room temperature. SnCl2(0.82 g, 4.33 mmol) was slowly added under nitrogen stream, and the reaction mixture was refluxed for 12 hours, and then cooled to room temperature. Water was added dropwise to quench the reaction. DCM (50 mL) was added to the mixture, and the mixture was washed with saturated aqueous sodium chloride solution (50 mL) for 3 times. The collected organic phase was dried over anhydrous sodium sulfate, and the organic solvent was removed by rotary evaporation; finally, column chromatography was performed using petroleum ether / DCM (volume ratio 2:1) as the eluent to obtain target compound I-1-2 as a yellow powder solid (345 mg, 0.61 mmol) with a yield of 70%. MS (EI) m / z: [M]+ + 616.13.

[0080] Example 3

[0081] The synthetic route of the target compound I-1-6 of this example is as follows:

[0082] Synthetic steps:

[0083] 3.2 Synthesis of intermediate 1-a: The synthetic procedure of intermediate 1-a is the same as described in Example 1.

[0084] 3.2 Synthesis of intermediate 3-b: Under anhydrous and anaerobic conditions, intermediate 1-a (1.78 g, 3.0 mmol), elemental sulfur (0.32 g, 10.0 mmol), elemental iodine (76 mg, 0.3 mmol) and 30 mL of o-dichlorobenzene were added into a 100 mL reaction flask, and the reaction was heated to 180 °C for 12 hours. After the reaction was cooled to room temperature, 50 mL of saturated sodium thiosulfate solution was added to quench the elemental iodine. DCM (100 mL) was added to the mixture, and the organic phase was washed with water (100 mL) for 3 times. The collected organic phase was dried over anhydrous sodium sulfate, and the organic solvent was removed by rotary evaporation; finally, column chromatography was performed using petroleum ether / DCM (volume ratio 6:1) as the eluent to obtain intermediate 3-b as a yellow powder solid (1.17 g, 1.8 mmol) with a yield of 60%. MS (EI) m / z: [M] + 652.20.

[0085] 3.3 Synthesis of target compound I-1-6: Intermediate 3-b (1.95 g, 3.0 mmol), 20 mL of acetic acid and 10 mL of hydrogen peroxide were added into a 100 mL reaction flask, and the reaction was carried out at 60 °C for 10 hours. After the reaction was cooled to room temperature, the reaction solution was poured into 200 mL of saturated sodium thiosulfate solution, and stirred at room temperature for 30 minutes to quench the residual hydrogen peroxide. DCM (100 mL) was added to the mixture, and the organic phase was washed with saturated aqueous sodium chloride solution (100 mL) for 3 times. The collected organic phase was dried over anhydrous sodium sulfate, and the organic solvent was removed by rotary evaporation; finally, column chromatography was performed using petroleum ether / DCM (volume ratio 4:1) as the eluent to obtain target compound I-1-6 as a white powder solid (1.93 g, 2.7 mmol) with a yield of 90%. MS (EI) m / z: [M] + 716.18.

[0086] Example 4

[0087] The synthetic route of the target compound I-1-130 of this example is as follows:

[0088] Synthetic steps:

[0089] 4.1 Synthesis of intermediate 4-a: In a 500 mL reaction flask, 2,6-dibromoanthracene (3.41 g, 10.0 mmol), DMAC (4.34 g, 20.0 mmol), palladium acetate (0.24 g, 1.0 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.6 g, 2.0 mmol) and sodium tert-butoxide (3.84 g, 40 mmol) were dissolved in 100 mL of toluene, which was then distilled again, and the mixture was heated to 110 °C overnight under anhydrous and anaerobic conditions. After the reaction was completed, the reaction solution was cooled, extracted with DCM and water three times, and the organic phase was combined. A small amount of saturated brine was added to the organic phase, which was then dried over anhydrous sodium sulfate, and the organic solvent was removed by rotary evaporation. Finally, column chromatography was performed using petroleum ether / ethyl acetate (10:1 by volume) as the eluent to obtain intermediate 4-a as a yellow powder solid (5.17 g, 0.85 mmol) with a yield of 85%.

[0090] 4.2 Synthesis of target compound I-1-130: A mixture of intermediate 4-a (1.23 g, 2.0 mmol), Pd(OAc)2(0.27 g, 1.2 mmol), silver oxide (1.38 g, 0.60 mmol), tri-tert-butylphosphonium tetrafluoroborate (1.15 g, 12 mmol), tert-pentanoic acid (15 mL) and K2CO3(3.90 g, 12.0 mmol) was added to a 100 mL reaction flask and refluxed under argon for 2 h. After cooling to room temperature, the reaction mixture was neutralized with saturated NaHCO3solution, and then extracted with brine and DCM. The collected organic phase was dried by rotary evaporation, and column chromatography was performed on silica gel using DCM / petroleum ether (15:1 by volume) as the eluent to obtain target compound I-1-130 (0.49 mg, 0.8 mmol). The yield was 40%. MS (EI) m / z: [M]+ + 608.39.

[0091] Example 5

[0092] The synthesis route of target compound I-1-36 of this example is as follows:

[0093] Synthesis steps:

[0094] 5.1 Synthesis of intermediate I-1-2: The synthesis of intermediate I-1-2 was performed according to the description in Example 2.

[0095] 5.2 Synthesis of target compound I-1-36: To the cooled 100 mL of dichloromethane was added 25 mL of 1 mol / L titanium (IV) chloride in dichloromethane solution (25 mmol) dropwise at -25 °C, then 12.6 mL of 2 mol / L dimethylzinc in toluene solution (25.2 mmol) was added dropwise, and the reaction mixture was stirred at -25 °C for 30 min. Then a solution of intermediate I-1-2 (0.78 g, 1.26 mmol) in dichloromethane (15 mL) was added dropwise. The mixture was stirred at -25 °C for 12 h. After the reaction was completed, the organic layer was separated, and the aqueous layer was extracted with dichloromethane (10 mL) three times. The combined organic layer was dried with anhydrous MgSO4, filtered, and distilled under reduced pressure. The crude product was purified by silica gel column chromatography (dichloromethane / n-hexane: 1 / 4) to obtain the target compound I-1-36 as a white solid, 0.64 g, in a yield of 75%. MS (EI) m / z: [M] + 672.33.

[0096] Example 6

[0097] The synthesis route of the target compound I-2-1 of this example is as follows:

[0098] Synthesis steps:

[0099] 6.1 Synthesis of intermediate 6-a: Under anhydrous and anaerobic conditions, 2,7-dibromo- phenanthrene (3.39 g, 10.0 mmol), DMAC (4.18 g, 20.0 mmol), palladium acetate (0.24 g, 1.0 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.6 g, 2.0 mmol) and sodium tert-butoxide (3.84 g, 40 mmol) were dissolved in 100 mL of redistilled toluene in a 500 mL reaction flask, and the temperature was raised to 110 °C for overnight reaction. After the reaction was completed, the reaction liquid was cooled, extracted with DCM and water three times, and the organic phase was combined. A small amount of saturated brine was added to the organic phase, which was then dried with anhydrous sodium sulfate, and the organic solvent was removed by rotary evaporation. Finally, column chromatography was performed using petroleum ether / ethyl acetate (volume ratio 10:1) as the eluent to obtain intermediate 6-a as a yellow powder solid (5.03 g, 0.85 mmol) in a yield of 85%.

[0100] 6.2 Synthesis of target compound I-2-1 : Into a 100 mL reaction flask was added intermediate 6-a (1.06 g, 2.0 mmol), Pd(OAc)2(0.27 g, 1.2 mmol), silver oxide (1.38 g, 0.60 mmol), tri-tert-butylphosphonium tetrafluoroborate (1.15 g, 12 mmol), pivalic acid (15 mL) and K2CO3(3.90 g, 12.0 mmol), the mixture was refluxed under argon for 2 h, after cooling to room temperature, the mixture was neutralized with saturated NaHCO3solution, then the reaction mixture was extracted with brine and DCM. The collected organic phase was dried, and purified by column chromatography on silica gel with DCM / petroleum ether (volume ratio 15:1) as eluent to give target compound I-2-1 (0.47 mg, 0.8 mmol). The yield was 40%. MS (EI) m / z: [M]+ + 588.26.

[0101] Example 7

[0102] The synthetic route of target compound I-2-18 of this example is as follows:

[0103] Synthetic procedure:

[0104] 7.1 Synthesis of intermediate 7-a: Into a 500 mL reaction flask was added 1,3,6,8-tetrabromo-2,7-difluorophenanthrene (5 mmol, 2.63 g), cesium carbonate (20 mmol, 6.52 g), phenoxazine (12 mmol, 2.19 g), N,N-dimethylformamide (60 mL) under anhydrous and anaerobic conditions. The mixture was reacted at 120 °C under nitrogen atmosphere for 12 h. After the reaction was completed, the reaction solution was cooled, extracted with DCM and water three times, and the organic phases were combined. A small amount of saturated brine was added to the organic phase, which was then washed and dried over anhydrous sodium sulfate, and the organic solvent was removed by rotary evaporation. Finally, column chromatography was performed using petroleum ether / dichloromethane (volume ratio 9:1) as eluent to give intermediate 7-a as a white powder solid (3.48 g, 4 mmol) with a yield of 80%.

[0105] 7.2 Synthesis of target compound I-2-18: Under anhydrous and anaerobic conditions, intermediate 7-a (2 mmol, 1.70 g), Pd(OAc)2(0.54 g, 2.4 mmol), tri-tert-butylphosphonium tetrafluorob orate (2.30 g, 24 mmol), N,N-dimethylacetamide (30 mL) and K2CO3(7.80 g, 24.0 mmol) were added into a 100 mL reaction flask, and the mixture was reacted at 125 °C for 24 h under a nitrogen atmosphere. After the reaction was completed, the reaction solution was cooled, extracted with DCM and water three times, and the organic phases were combined. A small amount of saturated brine was added to the organic phase, which was then dried over anhydrous sodium sulfate, and the organic solvent was removed by rotary evaporation. Finally, column chromatography was performed using petroleum ether / dichloromethane (volume ratio 3:1) as the eluent to obtain the target compound I-2-18 as a white powder solid (0.53 g, 1 mmol) with a yield of 50%. MS (EI) m / z: [M]+ + 532.11.

[0106] Example 8

[0107] The synthesis route of the target compound I-1-47 of this example is as follows:

[0108] Synthesis steps:

[0109] 8.1 Synthesis of intermediate 8-a: Under anhydrous and anaerobic conditions, 2,7-dibromophenazine (3.36 g, 10.0 mmol), DMAC (4.18 g, 20.0 mmol), palladium acetate (0.24 g, 1.0 mmol), tri-tert-butylphosphonium tetrafluorob orate (0.6 g, 2.0 mmol) and sodium tert-butoxide (3.84 g, 40.0 mmol) were dissolved in 100 mL of toluene, and the solution was heated to 110 °C and reacted overnight. After the reaction was completed, the reaction solution was cooled, extracted with DCM and water three times, and the organic phases were combined. A small amount of saturated brine was added to the organic phase, which was then dried over anhydrous sodium sulfate, and the organic solvent was removed by rotary evaporation. Finally, column chromatography was performed using petroleum ether / ethyl acetate (volume ratio 10:1) as the eluent to obtain intermediate 8-a as a yellow powder solid (5.04 g, 0.85 mmol) with a yield of 85%.

[0110] 8.1 Synthesis of target compound I-1-47: A mixture of intermediate 1-a (1.18 g, 2.0 mmol), Pd(OAc)2(0.27 g, 1.2 mmol), silver oxide (1.38 g, 0.60 mmol), tri-tert-butylphosphonium tetrafluoroborate (1.15 g, 12 mmol), pivalic acid (15 mL) and K2CO3(3.90 g, 12.0 mmol) was added to a 100 mL reaction flask under argon and refluxed for 2 h, cooled to room temperature, then neutralized with saturated NaHCO3solution, after which the reaction mixture was extracted with brine and DCM. The collected organic phase was dried, and purified by column chromatography on silica gel with DCM / petroleum ether (volume ratio 15:1) as eluent to obtain target compound I-1-47 (0.47 g, 0.8 mmol). The yield was 40%. MS (EI) m / z: [M]+ + 590.25.

[0111] Example 9

[0112] The synthesis route of target compound I-2-38 of this example is as follows:

[0113] Synthesis steps:

[0114] 9.1 Synthesis of intermediate 9-a: Under anhydrous and anaerobic conditions, 3,8-dibromo-1,10-phenanthroline (3.38 g, 10.0 mmol), DMAC (4.18 g, 20.0 mmol), palladium acetate (0.24 g, 1.0 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.6 g, 2.0 mmol) and sodium tert-butoxide (03.84 g, 40 mmol) were dissolved in 100 mL of toluene, which was then heated to 110 °C overnight. After the reaction was completed, the reaction solution was cooled, extracted with DCM and water three times, and the organic phases were combined. A small amount of saturated brine was added to the organic phase, which was then dried with anhydrous sodium sulfate, and the organic solvent was removed by rotary evaporation. Finally, column chromatography was performed using petroleum ether / ethyl acetate (volume ratio 10:1) as the eluent to obtain intermediate 6-a as a yellow powder solid (5.05 g, 0.85 mmol), with a yield of 85%.

[0115] 9.2 Synthesis of target compound I-2-38: Into a 100 mL reaction flask was added intermediate 6-a (1.07 g, 2.0 mmol), Pd(OAc)2(0.27 g, 1.2 mmol), silver oxide (1.38 g, 0.60 mmol), tri-tert-butylphosphonium tetrafluoroborate (1.15 g, 12 mmol), pivalic acid (15 mL) and K2CO3(3.90 g, 12.0 mmol), the mixture was refluxed under argon for 2 h, after cooling to room temperature, it was neutralized with saturated NaHCO3solution, then the reaction mixture was extracted with brine and DCM. The collected organic phase was dried and purified by column chromatography on silica gel with DCM / petroleum ether (volume ratio 15:1) as eluent to give target compound I-2-38 (0.48 g, 0.8 mmol). Yield 40%. MS (EI) m / z: [M]+ + 590.25.

[0116] Example 10

[0117] The synthetic route of target compound I-1-52 of this example is as follows:

[0118] Synthetic steps:

[0119] 10.1 Synthesis of intermediate 8-a: The synthesis of intermediate 8-a was carried out according to the procedure described in Example 8.

[0120] 10.2 Synthesis of intermediate 8-b: Under anhydrous and oxygen-free conditions, into a 100 mL reaction flask was added intermediate 8-a (1.79 g, 3.0 mmol), elemental sulfur (0.32 g, 10.0 mmol), elemental iodine (76 mg, 0.3 mmol) and 30 mL of o-dichlorobenzene, the reaction was heated to 180 °C for 12 h. After the reaction was cooled to room temperature, 50 mL of saturated sodium thiosulfate solution was added to quench the elemental iodine. To the mixture was added DCM (100 mL), the organic phase was washed with water 100 mL for 3 times, the collected organic phase was dried over anhydrous sodium sulfate, the organic solvent was removed by rotary evaporation; finally column chromatography was performed using petroleum ether / DCM (volume ratio 6:1) as eluent to give intermediate 10-b as a yellow powder solid (1.18 g, 1.8 mmol), yield 60%.

[0121] 10.3 Synthesis of target compound I-1-52: In a 100 mL reaction flask, intermediate 10-b (1.96 g, 3.0 mmol), 20 mL acetic acid and 10 mL hydrogen peroxide were added and reacted at 60 °C for 10 hours. After the reaction was cooled to room temperature, the reaction solution was poured into 200 mL saturated sodium thiosulfate solution and stirred at room temperature for thirty minutes to quench the remaining hydrogen peroxide. To the mixture, DCM (100 mL) was added and the organic phase was washed with saturated aqueous sodium chloride solution 100 mL for 3 times. The collected organic phase was dried over anhydrous sodium sulfate and the organic solvent was removed by rotary evaporation; finally, column chromatography was performed using petroleum ether / DCM (volume ratio 4:1) as eluent to obtain the target compound I-1-52 as a white powder solid (1.94 g, 2.7 mmol) with a yield of 90%. MS (EI) m / z: [M] + 718.17.

[0122] The Mass Spectrometry (MS) and Elemental Analysis (EA) results of the target compounds synthesized in Examples 1-10 are shown in Table 1 below.

[0123] Table 1

[0124] The steady-state fluorescence spectra of the target compounds synthesized in Examples 1-10 and compound A of Comparative Example 1 in toluene solution (10 -5 mol / L) are shown in Figure 1. As can be seen from Figure 1, the emission light color of the compounds synthesized in the examples of the present application contains the blue light region, which can maintain a relatively narrow spectral color purity. Compared with compound A (the structural formula of compound A is referred to below), the target compounds synthesized in Examples 1-10 narrow the spectrum and no long-wave shoulder peak is observed on the right side, which is beneficial to the spectral color purity. The photophysical properties of the target compounds synthesized in Examples 1-10 and compound A are shown in Table 2. Among them, λ peak is the peak wavelength, FWHM is the full width at half maxima, and PLQY is the absolute photoluminescence quantum yield.

[0125] Table 2

[0126] It can be seen that, compared with compound A, the compounds provided in the examples of the present application not only can realize a narrower luminescence spectrum, but also the absolute photoluminescence quantum yield can reach more than 90%, the peak is in the range of 450-550 nm, and the blue or green light emission is exhibited.

[0127] The performance of the electroluminescent device comprising the above-mentioned compound is tested through specific device examples 1-10 and comparative examples 1-2. Among them, the schematic diagram of the film layer stack of the electroluminescent device is shown in Figure 2, wherein 1—glass and conductive glass (ITO anode) substrate layer; 2—hole injection layer (HAT-CN, 5 nm); 3—hole transport layer (TAPC, 30 nm); 4—electron blocking layer (TCTA, 15 nm); 5—light-emitting layer (20 nm); 6—hole blocking layer (PO-T2T, 20 nm); 7—electron transport layer (ANT-BIZ, 30 nm); 8—electron injection layer (LiQ, 2 nm); 9—cathode (Al, 100 nm).

[0128] Among them, the device examples 1-10 and the device comparative examples 1-2 are the same in other device structures except for the different materials of the light-emitting layer.

[0129] The light-emitting layer of device comparative example 1: compound A and mCBP, the evaporation ratio is 12:188.

[0130] The light-emitting layer of device comparative example 2: compound A, photosensitizer Ir(ppy)3 and light-emitting host material DMIC-TRZ, the evaporation ratio is 12:4:184.

[0131] The light-emitting layer of device example 1: the difference from device comparative example 2 is that compound A is replaced by compound I-1-1 synthesized in example 1.

[0132] The light-emitting layer of device example 2: the difference from device comparative example 2 is that compound A is replaced by compound I-1-2 synthesized in example 2.

[0133] The light-emitting layer of device example 3: the difference from device comparative example 2 is that compound A is replaced by compound I-1-6 synthesized in example 3.

[0134] The light-emitting layer of device example 4: the difference from device comparative example 2 is that compound A is replaced by compound I-1-130 synthesized in example 4.

[0135] The light-emitting layer of device example 5: the difference from device comparative example 2 is that compound A is replaced by compound I-1-36 synthesized in example 5.

[0136] The light-emitting layer of device example 6: the difference from device comparative example 2 is that compound A is replaced by compound I-2-1 synthesized in example 6.

[0137] The light-emitting layer of device example 7: the difference from device comparative example 2 is that compound A is replaced by compound I-2-18 synthesized in example 7.

[0138] Light-emitting layer of device example 8: The difference from device comparative example 2 is that compound A is replaced by compound I-1-47 synthesized in example 8.

[0139] Light-emitting layer of device example 9: The difference from device comparative example 2 is that compound A is replaced by compound I-2-38 synthesized in example 9.

[0140] Light-emitting layer of device example 10: The difference from device comparative example 2 is that compound A is replaced by compound I-1-52 synthesized in example 10.

[0141] The electroluminescent device described above can be made according to known methods in the art, for example, according to the method disclosed in reference (Adv. Mater. 2003, 15, 277.). The specific method is as follows: under high vacuum conditions, the hole injection layer, the hole transport layer, the electron blocking layer, the light-emitting layer, the hole blocking layer, the electron transport layer, the electron injection layer and the cathode are sequentially evaporated on a cleaned conductive glass (ITO) substrate. The device shown in Figure 2 is prepared by this method. The luminescent properties of the prepared device are recorded under a current density of 10 mA / cm 2 The luminescent properties of the prepared device are recorded under a current density of 10 mA / cm

[0142] Table 3

[0143] As can be seen from Table 3, compared with the electroluminescent device prepared in device comparative examples 1-2, the electroluminescent device prepared in device examples 1-10 provided by the embodiments of the present application has a lower operating voltage, a higher luminescent efficiency, and a higher service life.

[0144] In the above examples, the description of each example has its own focus, and the parts not described in detail in a certain example can be referred to the relevant description of other examples.

[0145] The above describes in detail a compound, an electroluminescent device and a display panel provided by the embodiments of the present application. The above description is only used to help understand the technical solutions of the present application and its core idea; the person skilled in the art modifies the technical solutions recorded in the above examples or makes equivalent replacement for part of the technical features, without making the essence of the corresponding technical solution deviate from the scope of the technical solutions of the embodiments of the present application.

Claims

1. A compound having the general structural formula shown in formula (I): wherein A1, A2, and A3 are independently selected from substituted or unsubstituted aromatic groups having 6 to 50 carbon atoms; X1and X3are independently selected from a bond, a single bond, a carbonyl group, a sulfone group, an isopropyl group, or a substituted or unsubstituted arylalkyl group having 6 to 50 carbon atoms, and at most one of X1and X3is selected from a bond; X2is selected from a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 50 carbon atoms, an oxygen atom, a sulfur atom, a selenium atom, a carbonyl group, a sulfone group, or a sulfoxide group, when X2contains at least one benzene ring, A1forms a ring with an adjacent benzene ring in X2or does not form a ring with an adjacent benzene ring in X2, and A2forms a ring with an adjacent benzene ring in X2or does not form a ring with an adjacent benzene ring in X2.

2. The compound of claim 1, wherein, The compounds are selected from at least one of the following compounds of formulae (I-1) to (I-2): wherein A1and A2are independently selected from substituted or unsubstituted aromatic groups having 6 to 30 carbon atoms; Y1, Y2, Y3, and Y4are independently selected from C or N; X1and X3are independently selected from a bond, a single bond, a carbonyl group, a sulfone group, an isopropyl group, or an arylalkyl group having 7 to 30 carbon atoms, and at most one of X1and X3is selected from a bond; X2is selected from a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, an oxygen atom, a sulfur atom, a selenium atom, a carbonyl group, a sulfone group, or a sulfoxide group, when X2contains at least one benzene ring, A1forms a ring with an adjacent benzene ring in X2or does not form a ring with an adjacent benzene ring in X2, and A2forms a ring with an adjacent benzene ring in X2or does not form a ring with an adjacent benzene ring in X2. R1, R2, R3, and R4are independently selected from hydrogen, deuterium, tritium, a cyano group, a nitro group, a carbonyl group, a sulfone group, a halogen atom, a substituted or unsubstituted linear alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted silyl group having 1 to 20 carbon atoms, an aromatic fused ring group having 6 to 50 carbon atoms, and R3and R4form a ring or do not form a ring. X2is selected from the substituted or unsubstituted arylamine group having 6 to 50 carbon atoms, A1forms a ring with an adjacent benzene ring in X2, and A2does not form a ring with an adjacent benzene ring in X2; and X2is selected from the substituted or unsubstituted arylalkyl group having 6 to 50 carbon atoms, A1does not form a ring with an adjacent benzene ring in X2, and A2forms a ring with an adjacent benzene ring in X2or does not form a ring with an adjacent benzene ring in X2.

3. The compound of claim 1 or 2, wherein, 4. The compound according to claim 2, wherein A1and A2are selected from substituted or unsubstituted phenyl groups; Y1and Y2are the same, and Y3and Y4are the same. R1, R2, R3, and R4are independently selected from hydrogen, deuterium, tritium, a cyano group, a nitro group, a carbonyl group, a sulfone group, a halogen atom, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a silyl group having 1 to 10 carbon atoms, and R3and R4do not form a ring.

5. The compound of claim 2, wherein, ​ 6. The compound of claim 2, wherein, X1and X3are independently of each other selected from the group consisting of a single bond, a carbonyl group, a sulfone group, an isopropyl group, or an arylalkyl group having 7 to 20 carbon atoms, and at most one of X1and X3is selected from a single bond.

7. The compound of claim 2, wherein, The compounds are selected from at least one of the compounds shown in the following structural formulas I-1-1 to I-1-129, I-2-1 to I-2-96:

8. An electroluminescent device comprising an anode and a cathode, and a light-emitting layer between the anode and the cathode, the light-emitting layer comprising at least one functional material and a compound; The structural formula of the compound is shown as formula (I): wherein A1, A2, and A3are independently of each other selected from a substituted or unsubstituted aromatic group having 6 to 50 carbon atoms; X1and X3are independently of each other selected from the group consisting of a single bond, a carbonyl group, a sulfone group, an isopropyl group, or a substituted or unsubstituted arylalkyl group having 6 to 50 carbon atoms, and at most one of X1and X3is selected from a single bond. X2is selected from a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 50 carbon atoms, an oxygen atom, a sulfur atom, a selenium atom, a carbonyl group, a sulfone group, or a sulfoxide group, when X2contains at least one benzene ring, A1is annelated or not annelated with an adjacent benzene ring of X2, and A2is not annelated with an adjacent benzene ring of X2.

9. The electroluminescent device according to claim 8, wherein, The compounds are selected from at least one of the following compounds of formulae (I-1) to (I-2): wherein A1and A2are independently of each other selected from a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms; Y1, Y2, Y3, and Y4are independently of each other selected from C or N; X1and X3are independently of each other selected from the group consisting of a single bond, a carbonyl group, a sulfone group, an isopropyl group, or an arylalkyl group having 7 to 30 carbon atoms, and at most one of X1and X3is selected from a single bond. X2is selected from a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, an oxygen atom, a sulfur atom, a selenium atom, a carbonyl group, a sulfone group, or a sulfoxide group, when X2contains at least one benzene ring, A1is annelated or not annelated with an adjacent benzene ring of X2, and A2is not annelated with an adjacent benzene ring of X2. R1, R2, R3, and R4are independently of each other selected from hydrogen, deuterium, tritium, a cyano group, a nitro group, a carbonyl group, a sulfone group, a halogen atom, a substituted or unsubstituted linear alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted silyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic fused ring group having 6 to 50 carbon atoms, and R3and R4are annelated or not annelated.

10. An electroluminescent device according to claim 8 or 9, wherein, X2is selected from the substituted or unsubstituted arylamine group having 6 to 50 carbon atoms, A1is annelated with an adjacent benzene ring of X2, and A2is not annelated with an adjacent benzene ring of X2; X2is selected from the substituted or unsubstituted arylalkyl group having 6 to 50 carbon atoms, A1is not annelated with an adjacent benzene ring of X2, and A2is annelated or not annelated with an adjacent benzene ring of X2.

11. The electroluminescent device according to claim 9, wherein A1and A2are selected from substituted or unsubstituted phenyl; Y1and Y2are the same, and Y3and Y4are the same.

12. The electroluminescent device according to claim 9, wherein, R1, R2, R3, and R4are each independently selected from hydrogen, deuterium, tritium, a cyano group, a nitro group, a carbonyl group, a sulfone group, a halogen atom, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, a cyclic alkyl group having 3 to 10 carbon atoms, a silyl group having 1 to 10 carbon atoms, and R3and R4do not form a ring.

13. The electroluminescent device according to claim 9, wherein, X1and X3are each independently selected from a bond, a single bond, a carbonyl group, a sulfone group, an isopropyl group, or an arylalkyl group having 7 to 20 carbon atoms, and at most one of X1and X3is selected from a bond.

14. The electroluminescent device of claim 8, wherein, The at least one functional material includes a host light-emitting material and a first guest light-emitting material, and the at least one functional material further includes a second guest light-emitting material, and the compound is the second guest light-emitting material.

15. A display panel comprising a compound having the general structure of Formula (I): ###0002### (I) wherein A1, A2, and A3are each independently selected from a substituted or unsubstituted aromatic group having 6 to 50 carbon atoms; X1and X3are each independently selected from a bond, a single bond, a carbonyl group, a sulfone group, an isopropyl group, or a substituted or unsubstituted arylalkyl group having 6 to 50 carbon atoms, and at most one of X1and X3is selected from a bond; X2is selected from a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 50 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 50 carbon atoms, an oxygen atom, a sulfur atom, a selenium atom, a carbonyl group, a sulfone group, or a sulfoxide group, and when X2contains at least one benzene ring, A1forms a ring or does not form a ring with an adjacent benzene ring, and A2forms a ring or does not form a ring with an adjacent benzene ring. Alternatively, the display panel includes an electroluminescent device, the electroluminescent device includes an anode and a cathode, and a light-emitting layer between the anode and the cathode, the light-emitting layer includes at least one functional material and the compound.

16. The display panel of claim 15, wherein, The compounds are selected from at least one of the following compounds of formulae (I-1) to (I-2): wherein A1and A2are each independently selected from a substituted or unsubstituted aromatic group having 6 to 30 carbon atoms; Y1, Y2, Y3, and Y4are each independently selected from C or N; X1and X3are each independently selected from a bond, a single bond, a carbonyl group, a sulfone group, an isopropyl group, or an arylalkyl group having 7 to 30 carbon atoms, and at most one of X1and X3is selected from a bond. X2is selected from a substituted or unsubstituted alkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted arylamine group having 6 to 30 carbon atoms, an oxygen atom, a sulfur atom, a selenium atom, a carbonyl group, a sulfone group, or a sulfoxide group, and when X2contains at least one benzene ring, A1forms a ring or does not form a ring with an adjacent benzene ring, and A2forms a ring or does not form a ring with an adjacent benzene ring. R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, deuterium, tritium, a cyano group, a nitro group, a carbonyl group, a sulfone group, a halogen atom, a substituted or unsubstituted linear alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted branched alkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, a substituted or unsubstituted silyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aromatic fused ring group having 6 to 50 carbon atoms, and R3 and R4 are cyclic or acyclic.

17. The display panel of claim 15 or 16, wherein, X2 is selected from the group consisting of a substituted or unsubstituted aromatic amine group having 6 to 50 carbon atoms, A1 is cyclic with the adjacent benzene ring in X2, and A2 is acyclic with the adjacent benzene ring in X2; and X2 is selected from the group consisting of a substituted or unsubstituted arylalkyl group having 6 to 50 carbon atoms, A1 is acyclic with the adjacent benzene ring in X2, and A2 is cyclic or acyclic with the adjacent benzene ring in X2.

18. The display panel of claim 16, wherein, A1 and A2 are selected from the group consisting of a substituted or unsubstituted phenyl group; Y1 and Y2 are the same, and Y3 and Y4 are the same.

19. The display panel of claim 16, wherein, R1, R2, R3, and R4 are independently selected from the group consisting of hydrogen, deuterium, tritium, a cyano group, a nitro group, a carbonyl group, a sulfone group, a halogen atom, a linear alkyl group having 1 to 10 carbon atoms, a branched alkyl group having 3 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a silyl group having 1 to 10 carbon atoms, and R3 and R4 are acyclic.

20. The display panel of claim 16, wherein, X1 and X3 are independently selected from the group consisting of no bond, a single bond, a carbonyl group, a sulfone group, an isopropyl group, or an arylalkyl group having 7 to 20 carbon atoms, and at most one of X1 and X3 is selected from no bond.

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