Boron-containing compound, electroluminescent device, and display panel

Abstract

Disclosed are a boron-containing compound, an electroluminescent device, and a display panel. The structural general formula of the boron-containing compound is (I); formula (II) and formulae (III) to (IV) are selected from an aryl group or a heteroaryl group; R1 to R3 are selected from hydrogen, deuterium, halogen, -CN, -NO2, -CF3, -OH, -SH, -NH2, a linear hydrocarbon group, a branched hydrocarbon group, a cycloalkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryl ether group, a heteroaryl group, or a heteroaryl ether group; R is selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -NR4-, -POR4-, -O-, -S-, -Se-, -Te-, -SO-, or -SO2-; G is selected from a nitrogen atom or a phosphine oxide group; X, Y, and Z are selected from carbon or nitrogen.

Description

Boron-containing compound, electroluminescent device and display panel

[0001] This application claims priority to Chinese Patent Application No. 202410480910.8, filed on April 19, 2024, the entire contents of which are incorporated herein by reference. TECHNICAL FIELD

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

[0003] An organic light-emitting diode (OLED) has a wide application prospect in the fields of flexible display and solid-state lighting due to its advantages of self-luminescence, high contrast, wide viewing angle, high luminous efficiency, fast response, thinness, foldability and the like. The core of an OLED is a guest light-emitting material. The guest light-emitting material has developed from a traditional fluorescent material to a phosphorescent material, and then to a thermally activated delayed fluorescence (TADF) material in recent years. Under electrically excited, the ratio of singlet exciton to triplet exciton is 1:3. In a fluorescent material, triplet excitons are transition-forbidden, so the fluorescent material can only utilize 25% of singlet excitons, resulting in that the efficiency of the corresponding electroluminescent device is difficult to break through 5%. A phosphorescent material can utilize the spin-orbit coupling effect of a heavy metal atom, and can utilize triplet excitons to radiate transition luminescence. However, the stability of a blue phosphorescent material is poor, and deep blue light emission cannot be achieved. A thermally activated delayed fluorescence material is a material with a small singlet-triplet energy level difference, which makes triplet excitons reach an excited singlet state through a reverse intersystem crossing (RISC) process, and then radiate transition luminescence, realizing the utilization of triplet excitons. However, the lifetime of such a material is mostly short, and the half-peak width of the luminescence peak is wide, resulting in low color purity of luminescence, which cannot meet the needs of industrial applications.

[0004] Based on the above-mentioned defects, luminescent materials with high luminescent efficiency, high luminescent color purity and long luminescent lifetime need to be developed.

[0005] SUMMARY

[0006] The existing luminescent material has problems of luminescent efficiency, luminescent color purity and lifetime to be improved.

[0007] In a first aspect, an embodiment of the present application provides a boron-containing compound, a structure general formula of the boron-containing compound is shown as formula (I):

[0008] wherein, each independently selected from substituted or unsubstituted C6-C 60 aryl, or substituted or unsubstituted C5-C 60 heteroaryl;

[0009] R1, R2, R3are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, -CN, -NO2, -CF3, -OH, -SH, -NH2, a linear hydrocarbon group of C1-C 30 branched hydrocarbon group of C3-C 30 cycloalkyl group of C3-C 30 alkoxy group of C1-C 30 alkylthio group of C1-C 30 aryl group of C6-C 60 aryloxy group of C6-C 60 aromatic ether group of C6-C 60 heteroaryl group of C5-C 60 heteroaromatic ether group of C5-C ;

[0010] R is independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -NR4-, -POR4-, -O-, -S-, -Se-, -Te-, -SO-, or -SO2- at each occurrence; R4and R5are each independently selected from H, an alkyl group of C1-C 30 aryl group of C6-C 30 ;

[0011] G is selected from a nitrogen atom or phosphine oxide;

[0012] X, Y, Z are each independently selected from a carbon atom or a nitrogen atom.

[0013] In a second aspect, the embodiments of the present application further provide an electroluminescent device, comprising an anode and a cathode, and a light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises the above-mentioned boron-containing compound.

[0014] In a third aspect, the embodiments of the present application further provide a display panel, comprising the above-mentioned boron-containing compound or the above-mentioned electroluminescent device. BRIEF DESCRIPTION OF DRAWINGS

[0015] The technical solutions and other beneficial effects of the present application will be apparent from the following detailed description of the embodiments of the present application, taken in conjunction with the accompanying drawings.

[0016] FIG. 1 is a schematic diagram of a film layer stack of an electroluminescent device provided by the embodiments of the present application. Embodiments of the present application

[0017] The present application provides a boron-containing compound, an electroluminescent device and a display panel. 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.

[0018] 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.

[0019] 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, halogen, alkyl group containing 1-20 carbon atoms, heterocyclic group containing 3-20 ring atoms, aromatic group containing 6-20 ring atoms, heteroaromatic group containing 5-20 ring atoms, -NR'R", silyl group, carbonyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, halogen formyl group, formyl group, isocyanate group, thiocyanate group, isothiocyanate group, hydroxyl group, trifluoromethyl group, and the above-mentioned groups can be further substituted with an acceptable substituent in the art; it is understood that R' and R" in -NR'R" are each independently selected from, but not limited to, H, deuterium, tritium, cyano, isocyano, nitro or halogen, alkyl group containing 1-10 carbon atoms, heterocyclic group 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, halogen, adamantane, methyl, methoxy, trifluoromethyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, sec-butyl, neopentyl, n-pentyl, isopentyl, octyl, heptyl, n-decyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 1-butylpentyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, adamantyl and cycloheptyl, phenyl, biphenyl, terphenyl, naphthyl, anthryl, pyrenyl, phenanthryl, pyridyl, pyrimidyl, pyrazinyl, quinolyl, isoquinolyl, naphthridyl, oxazolyl, benzoxazolyl, imidazolyl, benzimidazolyl, furanyl, thienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-4-methylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl.

[0020] In the present application, the number of atoms described by a numerical range includes both the integer endpoints of the numerical range, and also each integer within the two endpoints. For example, "C 1-10 "alkyl" means an alkyl group having 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10 carbon atoms. "Containing 3 to 10 ring atoms" means containing 3, 4, 5, 6, 7, 8, 9, or 10 ring atoms.

[0021] In the present application, "the number of ring atoms" means the number of atoms among the atoms constituting a ring itself of a structured compound obtained by bonding atoms into a ring shape (e.g., monocyclic compound, fused ring compound, crosslinked compound, carbocyclic compound, heterocyclic compound). When the ring is substituted with a substituent, the atoms included in the substituent are not included in the ring-forming atoms. The same applies to "the number of ring atoms" described below, unless otherwise specified. For example, the number of ring atoms of a benzene ring is 6, the number of ring atoms of a naphthalene ring is 10, and the number of ring atoms of a thienyl group is 5. For example, the number of ring atoms of a methylbenzene is 6.

[0022] "Aryl" or "Aromatic group" means an aromatic hydrocarbon group derived by removing a hydrogen atom from an aromatic ring compound, and can be a monocyclic aryl group, or a fused ring aryl group, or a polycyclic aryl group, of which at least one is an aromatic ring system. For example, "Substituted or unsubstituted C6-C 60 "aryl" means an aryl group containing 6 to 60 carbon atoms, preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, more preferably a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, particularly preferably a substituted or unsubstituted aryl group having 6 to 14 carbon atoms, and the aryl group is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, pyrenyl, perylenyl, naphthacene, fluorenyl, rylene, acenaphthyl, and derivatives thereof. Understandably, multiple aryl groups can 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-dialkylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl.

[0023] "Heteroaryl" or "Heteroaromatic group" means an aromatic group in which at least one carbon atom is replaced by a non-carbon atom (heteroatom), which can be an oxygen, sulfur, selenium, tellurium, nitrogen atom, etc. For example, "Substituted or unsubstituted C5-C 60"Heteroaryl" refers to a heteroaromatic group having 5 to 60 carbon atoms, preferably a substituted or unsubstituted heteroaromatic group having 5 to 30 carbon atoms, more preferably a substituted or unsubstituted heteroaromatic group having 5 to 18 carbon atoms, particularly preferably a substituted or unsubstituted heteroaromatic group having 5 to 14 carbon atoms, and the heteroaromatic group can be optionally further substituted, suitable examples include, but are not limited to: thienyl, furanyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, perylenyl, phenanthridinyl, berberinyl, quinazolinonyl, dibenzothienyl, dibenzofuranyl, carbazolyl, and derivatives thereof.

[0024] In the present application, "alkyl" can mean straight chain, branched chain, and / or cyclic alkyl. The number of carbons of the alkyl group can be 1 to 50, 1 to 30, 1 to 20, 1 to 10, or 1 to 6. Non-limiting examples of alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, t-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, t-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantyl, and the like.

[0025] In the present application, substituent abbreviations correspond to: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-met, p-para, Me-methyl, Et-ethyl, Pr-propyl, Bu-butyl, Am-n-amyl, Hx-hexyl, Cy-cyclohexyl.

[0026] "halogen" or "halogen atom" means F, Cl, Br, or I.

[0027] The term "alkoxy" refers to a group whose structure is "-O-alkyl", i.e., an alkyl group as defined above attached to another group through an oxygen atom. Suitable examples include, but are not limited to: methoxy (-O-CH3 or -OMe), ethoxy (-O-CH2CH3 or -OEt), and t-butoxy (-O-C(CH3)3 or -OtBu).

[0028] In the present application, "further", "even further", "in particular" and the like are used for descriptive purposes only and should not be understood as limiting the scope of the present application.

[0029] In the present application, "optionally", "optional" or "optional" means that it can or can not exist, that is, it means that it is selected from any one of the two parallel schemes of "has" or "has not". If there are multiple "options" in a technical solution, unless otherwise specified, and there is no contradiction or mutual restriction relationship, each "option" is independent.

[0030] In the present application, when describing various groups, if the substitution situation is not emphasized, it is assumed that the group is unsubstituted. For example, "C1-C 30 alkyl" refers to unsubstituted C1-C 30 alkyl, "C6-C 60 aryl" refers to unsubstituted C6-C 60 aryl.

[0031] In the present application, in the technical features described in an open manner, both the closed technical solution consisting of the listed features and the open technical solution containing the listed features are included.

[0032] The structure general formula of the boron-containing compound provided by the embodiments of the present application is shown in the following formula (1):

[0033] Among them, is selected from substituted or unsubstituted C6-C 60 aryl, or substituted or unsubstituted C5-C 60 heteroaryl.

[0034] Each is independently selected from substituted or unsubstituted C6-C 60 aryl, or substituted or unsubstituted C6-C 60 heteroaryl.

[0035] R1, R2, R3 are each independently selected from hydrogen atom, deuterium atom, halogen atom, -CN, -NO2, -CF3, -OH, -SH, -NH2, C1-C 30 linear alkyl, C3-C 30 branched alkyl, C3-C 30 cycloalkyl, C1-C 30 alkoxy, C1-C 30 alkylthio, C6-C 60 aryl, C6-C 60 aryloxy, C5-C 60 heteroaryl, or C5-C 60 heteroaryloxy.

[0036] R is, at each occurrence, independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -NR4-, -POR4-, -O-, -S-, -Se-, -Te-, -SO-, or -SO2-; R4and R5are each independently selected from H, C1-C 30 alkyl, or C6-C 30 aryl.

[0037] G is selected from a nitrogen atom or phosphine oxide, X, Y, Z are each independently selected from a carbon atom or a nitrogen atom.

[0038] The existing boron-containing compounds have a large conjugated planar structure, and are prone to concentration quenching under electric excitation, and the device has a serious efficiency roll-off problem. The boron-containing compound provided in the embodiments of the present application introduces a large steric heterocyclic aromatic fragment, so that the molecule presents a certain degree of twisted structure, effectively inhibits the concentration quenching effect, and the introduction of heteroatoms such as oxygen and sulfur is beneficial to enhancing the spin-orbit coupling effect of the molecule, so that the molecule has a short delay lifetime, which is beneficial to improve the efficiency roll-off problem of the device. The electroluminescent device and the display panel based on the boron-containing compound have higher luminous efficiency and good device lifetime.

[0039] The boron-containing compound provided in the embodiments of the present application has a steady-state fluorescence spectrum wavelength range of 430-580 nm in toluene solution (10 -5 mol / L), and the half-peak width of the spectrum is less than 35 nm; the transient luminescence under a solid-state thin film has a delayed luminescence, and the lifetime is 1 us-100 ms.

[0040] In some embodiments of the present application, is selected from a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, or a substituted or unsubstituted anthracene group. When the above-mentioned group is substituted, the substituents of the above-mentioned group can be mutually annulated with the above-mentioned group. Through the design of the above-mentioned group , the molecule of the boron-containing compound can be asymmetrically substituted, and under electric excitation, a better horizontal dipole orientation can be easily obtained, thereby enhancing the light extraction efficiency of the device.

[0041] Specifically, may be selected from any one of the following structures:

[0042] wherein "*" represents a connection site;

[0043] R 1 may be independently selected from H, a substituted or unsubstituted C6-C 40 aryl, or a substituted or unsubstituted C5-C 40 heteroaryl at each occurrence;

[0044] In some embodiments, adjacent R 1 may or can not form a ring.

[0045] In some embodiments of the present application, the boron-containing compound has a structure according to Formula (I-1) or Formula (I-2):

[0046] to each independently selected from substituted or unsubstituted C6-C 30 aryl, or substituted or unsubstituted C6-C 30 heteroaryl.

[0047] Optionally, to each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted indolyl, substituted or unsubstituted naphthyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted triphenylamino.

[0048] R1, R2, R3are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, -CN, -NO2, -CF3, -OH, -SH, -NH2, a linear hydrocarbon group of C1-C 30 , a branched hydrocarbon group of C3-C 30 , a cyclic hydrocarbon group of C3-C 30 , an alkoxy group of C1-C 30 , an alkylthio group of C1-C 30 , an aryl group of C6-C 60 , an aryloxy group of C6-C 60 , a heteroaryl group of C5-C 60 , or a heteroaryloxy group of C5-C 60 .

[0049] R is independently selected at each occurrence from a single bond, -CR4R5-, -CO-, -SiR4R5-, -NR4-, -POR4-, -O-, -S-, -Se-, -Te-, -SO-, or -SO2-; R4and R5are each independently selected from H, an alkyl group of C1-C 30 , or an aryl group of C5-C 30 .

[0050] By alternating the electron-deficient B element with the electron-rich N element, the multi-resonance thermal activated delayed fluorescence (MR-TADF) is constructed by using the opposite resonance effect of B and N atoms. The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) are induced to be located on different atoms by the multi-resonance effect, so that the bonding / antibonding characteristics between atoms are weakened, the change of electron density between atoms caused by the lowest excited state to the ground state radiation transition is largely reduced, and the stretching vibration is reduced, so that narrow spectrum emission (FWHM<30nm) is effectively realized. At the same time, the thermal activated delayed fluorescence property of the molecule also ensures the high luminous efficiency of the material.

[0051] The boron-containing compound having the above formula (I-1) or (I-2) is easy to obtain a better horizontal dipole orientation under the condition of electrically excited by designing an asymmetrically substituted boron-nitrogen molecule, and the light-emitting efficiency of the device can be enhanced. Under the premise of affecting the spectral full width at half maximum, the introduction of a large steric hindrance heterocyclic aromatic fragment makes the molecule present a certain twisted structure, which is helpful to inhibit the concentration quenching effect. The introduction of heteroatoms such as oxygen and sulfur is beneficial to enhance the spin-orbit coupling effect of the molecule, so that the molecule has a shorter delay lifetime, which is helpful to alleviate the efficiency roll-off problem of the device.

[0052] Optionally, in some embodiments, At Each of R1, R2, and R3 is independently selected from a phenyl group, a benzothiophene group, a biphenyl group, a naphthyl group, a quinazoline group, a carbazole group substituted with a benzene, or a dibenzofuran group, which is substituted or unsubstituted with a deuterium atom, -CH3, -C(CH3)3, -CF3, -CN, or -OCH3.

[0053] Optionally, in some embodiments, R1, R2, and R3 are each independently selected from a hydrogen atom, CN, CF3, or -OCH3.

[0054] Optionally, in some embodiments, R is independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -O-, -S-, -Se-, -Te-, -SO-, or -SO2- at each occurrence, and R4 and R5 are each independently selected from H, C1-C 10 alkyl, or C6-C 20 aryl.

[0055] Specifically, in some embodiments, the boron-containing compound is selected from one of the following compounds shown in the structural formula:

[0056] Based on the above-mentioned boron-containing compound, the 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 the above-mentioned boron-containing compound in the embodiment.

[0057] The light-emitting layer comprises a host light-emitting material, a sensitizer and a guest light-emitting material, and the boron-containing compound can be used as the guest light-emitting material.

[0058] In some embodiments, the sensitizer can be at least one of a phosphorescent material and a thermally activated delayed fluorescence material. Further, the sensitizer is preferably a material with a peak emission of 440-600 nm, phosphorescent emission and a phosphorescent lifetime of 1 us-100 ms. The HOMO energy level of the sensitizer ranges from -6.0 eV to -5.0 eV, and the LUMO energy level ranges from -3.0 to -4.0 eV.

[0059] Further, in some embodiments, the boron-containing compound is a compound represented by the structural formula with a peak emission spectrum of 480-580 nm, a spectral half-width of less than 60 nm, a HOMO energy level ranging from -6.0 eV to -5.0 eV, and a LUMO energy level ranging from -3.0 to -4.0 eV.

[0060] In some embodiments, the electroluminescent device can further comprise a hole injection layer, a hole transport layer and an electron blocking layer between the anode and the light-emitting layer, and stacked in sequence on the anode.

[0061] In some embodiments, the electroluminescent device further comprises a hole blocking layer, an electron transport layer and an electron injection layer between the light-emitting layer and the cathode, and stacked in sequence on the light-emitting layer.

[0062] 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 light-emitting 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.

[0063] In the embodiment of the present application, the anode can comprise a conductive metal, a metal oxide or a conductive polymer. The anode can easily inject holes into the hole injection layer, the hole transport layer or the light-emitting layer.

[0064] 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 suitable physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, e-beam, and the like.

[0065] In some embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to make electroluminescent devices according to the present application.

[0066] In the present application, the cathode can include a conductive metal or metal oxide. The cathode can readily inject electrons into the electron injection layer or electron transport layer or directly into the light-emitting layer.

[0067] In principle, all materials that can be used as a cathode for OLEDs 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 suitable physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, e-beam, and the like.

[0068] The hole injection material, hole transport material, hole blocking material, electron blocking material, electron transport material, and electron injection material used in the electroluminescent devices 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, hole transport material, electron blocking material, electron transport material, and electron injection material.

[0069] The present application also relates to the use of the electroluminescent devices according to the present 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. Display devices include, for example, but are not limited to, mobile phones, car displays, AR, VR, laptops, televisions, and the like.

[0070] The present application also provides a display panel comprising the electroluminescent device described above. The display panel can further comprise a pixel driving circuit for driving the electroluminescent device to emit light, wherein the pixel driving circuit is electrically connected to the electroluminescent device. The pixel driving circuit includes, but is not limited to, a thin film transistor driving circuit.

[0071] Specific Embodiments

[0072] The present application will be described in detail below by specific examples. The following examples are only part of the examples of the present application, and are not a limitation of the present application. The raw materials used in the following examples are commercially available products, unless otherwise specified. Among them, K2CO3: potassium carbonate; DMSO: dimethyl sulfoxide; Pd2(dba)3: tris(dibenzylideneacetone)dipalladium; S-Phos: 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl; t-BuONa: sodium tert-butoxide; tol: toluene; DCM: dichloromethane; CuI: copper(I) iodide; o-DCB: o-dichlorobenzene; n-BuLi: n-butyllithium; THF: tetrahydrofuran; m-xylene: m-xylene; BBr3: boron tribromide; iPr2NEt: N,N-diisopropylethylamine; (t-Bu)3PHBF4: tri-tert-butylphosphonium tetrafluoroborate; PA: pivalic acid; CH3MgBr: methylmagnesium bromide; Cs2CO3: cesium carbonate.

[0073] Example 1

[0074] The synthetic route of the target compound 1 of the present example is as follows:

[0075] Synthetic steps:

[0076] 1.1 Synthesis of intermediate 1-a: In a 500 mL two-necked flask, 1-bromo-2,6-dichlorobenzene (11.3 g, 50 mmol), 2,4-dibromocarbazole (19.5 g, 60 mmol), anhydrous potassium carbonate (9.66 g, 70 mmol) were added, and then purged with argon three times, and then dry dimethyl sulfoxide (150 mL) was added, and then reacted at 150°C for 48 h. After the reaction was cooled to room temperature, it was extracted three times with dichloromethane (300 mL x 3), and then the excess solvent was removed by a rotary evaporator, and then purified by column chromatography to obtain intermediate 1-a (22.14 g, yield 85%).

[0077] 1.2 Synthesis of intermediate 1-b: In a 500 mL two-necked flask, intermediate 1-a (18 g, 42 mmol), 9,9-dimethyl-9,10-dihydroacridine (10.45 g, 50 mmol), tris(dibenzylideneacetone)dipalladium (1.93 g, 2.1 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl (1.72 g, 4.2 mmol), sodium tert-butoxide (8.06 g, 84 mmol) were added, and then purged with argon three times, and then dry toluene (150 mL) was added, and then reacted at 110°C for 48 h. After the reaction was cooled to room temperature, it was extracted three times with dichloromethane (DCM) (300 mL x 3), and then the excess solvent was removed by a rotary evaporator, and then purified by column chromatography to obtain intermediate 1-b (22.6 g, yield 80%).

[0078] 1.3 Synthesis of Intermediate 1-c: Into a 500 mL reaction flask was added Intermediate 1-b (22.6 g, 33 mmol), m-xylene 330 mL, n-butyllithium in n-hexane (13.2 mL, 17.2 M, 33.66 mmol) was added dropwise to the reaction at -78 °C and stirred for 1 h before heating at 60 °C for 2 h, then low boiling solvent was removed under reduced pressure. After dropwise addition of boron tribromide (9.3 g, 37 mmol) at -78 °C, stirred at room temperature for 1 h, then dropwise addition of N,N-diisopropylethylamine (4.9 g, 37 mmol) at 0 °C, heated and stirred at 140 °C for 24 h. Cooled to room temperature, added aqueous sodium acetate solution and stirred, extracted the organic layer with DCM, concentrated and purified by column chromatography to give Intermediate 1-c (9.6 g, 15 mmol, 50% yield).

[0079] 1.4 Synthesis of Intermediate 1-d: Into a 500 mL two-necked flask was added Intermediate 1-c (9.6 g, 15 mmol), 9,9-dimethyl-9,10-dihydroacridine (6.27 g, 30 mmol), palladium acetate (180 mg, 0.75 mmol), tri-tert-butylphosphine tetrafluoroborate (705 mg, 2.25 mmol), sodium tert-butoxide (2.88 g, 30 mmol), purged with argon three times, added anhydrous toluene (150 mL), then reacted at 110 °C for 36 h. After the reaction was cooled to room temperature, extracted three times with dichloromethane (DCM) (200 mL x 3), removed the excess solvent with a rotary evaporator, then purified by column chromatography to give Intermediate 1-d (11.6 g, 80% yield).

[0080] 1.5 Synthesis of Target Compound 1: Into a 500 mL two-necked flask was added Intermediate 1-d (11.6 g, 12 mmol), palladium acetate (269 mg, 1.2 mmol), silver oxide (5.57 g, 24 mmol), purged with argon three times, added pivalic acid (120 mL), reacted at 150 °C for 6 h, then added anhydrous potassium carbonate (552 mg, 4 mmol) and continued to react for 12 h, after the reaction was cooled to room temperature, added saturated aqueous sodium bicarbonate solution and stirred, then extracted the organic layer with DCM, concentrated and purified by column chromatography to give the product, Target Compound 1 (5 g, 5.4 mmol, 45% yield).

[0081] Example 2

[0082] The synthesis route of the target compound 2 of this example is as follows:

[0083] Synthesis steps:

[0084] 2.1 Synthesis of intermediate 2-a: In a 250 mL two-necked flask was placed 10,15- dihydro-5H-dipyrido[3,2-A:3',2'-C]carbazole (20.7 g, 60 mmol), 2-bromoiodobenzene (44.7 g, 150 mmol), cuprous iodide (0.57 g, 3 mmol), copper powder (7.5 g, 120 mmol) and potassium carbonate (16.5 g, 120 mmol), purged with argon 3 times, added anhydrous o-dichlorobenzene (150 mL) and heated at 220 °C for 50 h. After the reaction was completed, it was cooled to room temperature, extracted with DCM and water 3 times, the organic phases were combined and the solvent was removed. Column chromatography gave intermediate 2-a (6 g, 9 mmol, 15% yield).

[0085] 2.2 Synthesis of intermediate 2-b: In a 500 mL two-necked flask was placed intermediate 2-a (6 g, 9 mmol), purged with argon 3 times, added anhydrous tetrahydrofuran (200 mL) and then the apparatus was cooled in a dry ice / acetone bath at -78 °C for 15 min. A solution of n-butyllithium in hexanes (45 mL, 18 mmol) was added dropwise to the reaction flask using a syringe and the reaction was stirred at -78 °C for a further 1 h. Diphenylchlorosilane was added and the reaction was stirred at room temperature for 12 h and then cooled to room temperature. Extracted with DCM and water 3 times, the organic phases were combined and the solvent was removed. Column chromatography gave intermediate 2-b (5.4 g, 60% yield).

[0086] 2.3 Synthesis of intermediate 2-c: In a 500 mL two-necked flask was placed intermediate 2-b (4.3 g, 5 mmol), 3,3-dimethyl-1-butene (3.2 mL, 25 mmol), RhCl(PPh3)3 (46 mg, 0.05 mmol), purged with argon 3 times, added anhydrous 1,4-dioxane (100 mL) and heated at 135 °C for 24 h. After the reaction was completed, it was cooled to room temperature, extracted with DCM and water 3 times, the organic phases were combined and the solvent was removed. Column chromatography gave intermediate 2-c (1.8 g, 84% yield).

[0087] 2.4 Synthesis of intermediate 2-d: In a 500 mL two necked flask was added 1-bromo-2,6-dichlorobenzene (452 mg, 2 mmol), phenothiazine (400 mg, 2 mmol), tris(dibenzylideneacetone)dipalladium (184 mg, 0.2 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl (82 mg, 0.2 mmol), sodium tert-butoxide (240 mg, 2.5 mmol) was purged with argon three times, dry toluene (200 mL) was added and then the reaction was heated at 110 °C for 24 h. After the reaction was cooled to room temperature, it was extracted with DCM three times and the excess solvent was removed using a rotary evaporator. The product was purified by column chromatography to obtain intermediate 2-d (577 mg, 75% yield).

[0088] 2.5 Synthesis of intermediate 2-e: In a 100 mL two necked flask was added intermediate 2-d (385 mg, 1 mmol), intermediate 2-c (860 mg, 1 mmol), anhydrous potassium carbonate (276 mg, 2 mmol) was purged with argon three times, dry dimethylsulfoxide (10 mL) was added and then the reaction was heated at 150 °C for 24 h. After the reaction was cooled to room temperature, it was extracted with DCM three times and the excess solvent was removed using a rotary evaporator. The product was purified by column chromatography to obtain intermediate 2-e (800 mg, 76% yield)

[0089] 2.6 Synthesis of compound 2: In a 100 mL two necked flask was added intermediate 2-e (600 mg, 0.5 mmol), m-xylene 10 mL, n-butyllithium in hexane (1 mol / L, 0.2 mL, 0.51 mmol) was added dropwise to the reaction mixture at -40 °C and stirred for 1 h. Then boron tribromide (190 mg, 0.75 mmol) was added dropwise at -78 °C and stirred at room temperature for 1 h. N,N-diisopropylethylamine (100 mg, 0.75 mmol) was added dropwise at 0 °C and heated at 150 °C for 24 h. After cooling to room temperature, the organic layer was extracted with DCM, concentrated and purified by column chromatography to obtain the product compound 2 (250 mg, 0.225 mmol, 45% yield).

[0090] Example 3

[0091] The synthetic route of the target compound 3 of this example is as follows:

[0092] Synthetic steps:

[0093] 3.1 Synthesis of Intermediate 3-a: In a 1000 mL reaction flask was added 2,4- dibromocarbazole (13.0 g, 40 mmol), phenoxazine (6.41 g, 35 mmol), palladium acetate (420 mg, 1.75 mmol), tri-tert-butylphosphonium tetrafluoroborate (1.0 g, 3.5 mmol), sodium tert-butoxide (2.45 g, 42 mmol), purged with argon three times, added anhydrous toluene (400 mL), then refluxed at 110 °C for 36 h. After the reaction was cooled to room temperature, extracted with DCM three times, removed excess solvent with a rotary evaporator, then purified by column chromatography to obtain Intermediate 3-a (10.2 g, 24 mmol, 70% yield).

[0094] 3.2 Synthesis of Intermediate 3-b: In a 500 mL two-necked flask was added Intermediate 3-a (10.2 g, 24 mmol), phenothiazine (4.88 g, 24 mmol), palladium acetate (288 mg, 1.2 mmol), tri-tert-butylphosphonium tetrafluoroborate (680 mg, 2.4 mmol), sodium tert-butoxide (1.75 g, 30 mmol), purged with argon three times, added anhydrous toluene (250 mL), then refluxed at 110 °C for 36 h. After the reaction was cooled to room temperature, extracted with DCM three times, removed excess solvent with a rotary evaporator, then purified by column chromatography to obtain Intermediate 3-b (9.8 g, 18 mmol, 75% yield).

[0095] 3.3 Synthesis of Intermediate 3-c: In a 500 mL two-necked flask was added Intermediate 3-b (9.8 g, 18 mmol), palladium acetate (410.4 mg, 1.8 mmol), silver oxide (4.17 g, 18 mmol), purged with argon three times, added pivalic acid (180 mL), reacted at 150 °C for 6 h, then added anhydrous potassium carbonate (412 mg, 3 mmol), continued to react for 12 h, after the reaction was cooled to room temperature, added saturated aqueous sodium bicarbonate solution and stirred until the solution system pH was neutral, then extracted the organic layer with DCM, concentrated and purified by column chromatography to obtain Intermediate 3-c (4.87 g, 9 mmol, 50% yield).

[0096] 3.4 Synthesis of intermediate 3-d: In a 250 mL two-necked flask, 1-bromo-2,6- dichlorobenzene (2.71 g, 12 mmol), 9,9-dimethyl-9,10-dihydroacridine (2.51 g, 12 mmol), tris(dibenzylideneacetone)dipalladium (265 mg, 0.6 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl (491 mg, 1.2 mmol), sodium tert-butoxide (1.92 g, 20 mmol) were purged with argon three times, dry toluene (100 mL) was added, and then the reaction was carried out at 110 °C for 48 h. After the reaction was cooled to room temperature, it was extracted with dichloromethane (DCM) three times (200 mL x 3), and then the excess solvent was removed by rotary evaporation. The intermediate 3-d (3.8 g, 9.6 mmol, 80% yield) was obtained by column chromatography.

[0097] 3.5 Synthesis of intermediate 3-e: In a 250 mL two-necked flask, intermediate 3-d (3.8 g, 9 mmol), intermediate 3-c (4.87 g, 9 mmol), anhydrous potassium carbonate (2.07 g, 15 mmol) were purged with argon three times, dry dimethyl sulfoxide (90 mL) was added, and then the reaction was carried out at 150 °C for 48 h. After the reaction was cooled to room temperature, it was extracted with DCM three times, and then the excess solvent was removed by rotary evaporation. The intermediate 3-e (6.3 g, 7 mmol, 80% yield) was obtained by column chromatography.

[0098] 3.6 Synthesis of target compound 3: To a 250 mL reaction flask, intermediate 3-e (6.3 g, 7 mmol), p-xylene 140 mL were added, and then n-butyllithium in n-hexane (2.8 mL, 3.65 M, 7.14 mmol) was added dropwise to the reaction system at -40 °C and stirred for 1 h. After the addition of boron tribromide (2.5 g, 10 mmol) dropwise at -78 °C, the reaction was stirred at room temperature for 1 h, and then N,N-diisopropylethylamine (1.27 g, 10 mmol) was added dropwise at 0 °C and stirred at 150 °C for 24 h. After cooling to room temperature, the organic layer was extracted with DCM, concentrated, and then purified by column chromatography to obtain the target compound 3 (2.33 g, 2.8 mmol, 40% yield).

[0099] Example 4

[0100] The synthesis route of the target compound 4 of the present example is as follows:

[0101] Synthesis steps:

[0102] 4.1 Synthesis of intermediate 4-a: In a 100 mL two necked flask, under argon atmosphere, trisindole (3.45 g, 10 mmol), cuprous iodide (380 mg, 2 mmol), copper powder (5 g, 80 mmol) and potassium carbonate (11 g, 80 mmol) were weighed, 50 mL of o-dichlorobenzene was added, 3.2 mL of methyl o-iodobenzoate (20 mmol) was added, the temperature was raised to 220 °C and stirred for 50 h under argon protection, then cooled to room temperature, extracted with DCM and water, the organic phase was separated, dried by adding anhydrous sodium sulfate, the organic phase obtained after filtration was removed from the solvent and purified by column chromatography to obtain intermediate 4-a (1.4 g, yield: 23%).

[0103] 4.2 Synthesis of intermediate 4-b: In a 100 mL two necked flask, under argon atmosphere, intermediate 4-a (1.2 g, 2 mmol) was added, 18 mL of anhydrous tetrahydrofuran was added, stirred, then 20 mL of methyl magnesium bromide (20 mmol) was added dropwise, after 12 h of reaction at 80 °C it was cooled to room temperature, extracted with ethyl acetate and water, the organic phase was separated, dried by adding anhydrous sodium sulfate, the organic phase obtained after filtration was removed from the solvent and purified by column chromatography to obtain intermediate 4-b (0.37 g, 0.6 mmol, yield: 30%).

[0104] 4.3 Synthesis of intermediate 4-c: In a 100 mL single necked flask, under argon atmosphere, intermediate 4-b (0.61 g, 1 mmol) was weighed, 20 mL of glacial acetic acid was added, 3 mL of concentrated hydrochloric acid was added, heated to 130 °C, reacted for 4 h, then cooled to room temperature, extracted with dichloromethane and water, the organic phase was separated, dried by adding anhydrous sodium sulfate, the organic phase obtained after filtration was removed from the solvent and purified by column chromatography to obtain intermediate 4-c (0.35 g, yield 60%).

[0105] 4.4 Synthesis of intermediate 4-d: In a 100 mL two necked flask, 1-bromo-2,6- dichlorobenzene (452 mg, 2 mmol), 10H-phenoselenazine (492 mg, 2 mmol), tris(dibenzylideneacetone)dipalladium (184 mg, 0.2 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'- biphenyl (82 mg, 0.2 mmol), sodium tert-butoxide (240 mg, 2.5 mmol) were added, purged three times under argon atmosphere, super dry toluene (20 mL) was added, then reacted for 24 h at 110 °C. After the reaction was allowed to reach room temperature, it was extracted three times with DCM, the excess solvent was removed with a rotary evaporator and purified by column chromatography to obtain intermediate 4-d (652 mg, 1.5 mmol, yield 75%).

[0106] 4.5 Synthesis of intermediate 4-e: In a 100 mL two necked flask was added intermediate 4-d (440 mg, 1 mmol), intermediate 4-c (575 mg, 1 mmol), anhydrous potassium carbonate (280 mg, 2 mmol), purged with argon three times, added dry dimethyl sulfoxide (20 mL) and then heated at 150 °C for 24 h. After cooling the reaction to room temperature, extracted with DCM three times, removed excess solvent using a rotary evaporator and purified by column chromatography to obtain the intermediate (750 mg, 0.75 mmol, 75% yield)

[0107] 4.6 Synthesis of target compound 4: In a 100 mL two necked flask was added intermediate 4-e (500 mg, 0.5 mmol), m-xylene 10 mL, added n-butyllithium in n-hexane solution (0.2 mL, 1 M, 0.51 mmol) drop wise to the reaction mixture at -40 °C and stirred for 1 h. Then added boron tribromide (188 mg, 0.75 mmol) drop wise at -78 °C, stirred at room temperature for 1 h, added N, N-diisopropylethylamine (100 mg, 0.75 mmol) drop wise at 0 °C and heated at 150 °C for 24 h. Cooled to room temperature, extracted the organic layer with DCM, concentrated and purified by column chromatography to obtain the target compound 4 (202 mg, 0.2 mmol, 40% yield).

[0108] Example 5

[0109] The synthesis route of the target compound 5 of this example is as follows:

[0110] Synthesis steps:

[0111] 5.1 Synthesis of intermediate 5-a: In a 100 mL two necked flask was taken trimer indole (3.45 g, 10 mmol), 1-(2-bromophenoxy)-2-butanone (13 g, 50 mmol), cuprous iodide (0.19 g, 1 mmol), copper powder (2.5 g, 40 mmol) and potassium carbonate (5.5 g, 40 mmol) under argon atmosphere, added 50 mL of o-dichlorobenzene, heated to 220 °C for 50 h and then cooled to room temperature, extracted with dichloromethane and water, separated the organic layer, dried by adding anhydrous sodium sulfate, removed the solvent using a rotary evaporator and purified by column chromatography to obtain the intermediate 5-a (1.5 g, 2 mmol, 20% yield).

[0112] 5.2 Synthesis of intermediate 5-b: Intermediate 5-a (1.5 g, 2 mmol) and CF3SO3H were added to a 100 mL two-necked flask and the mixture was stirred at room temperature for 24 h, then a mixture of water and pyridine (8:1 by volume) was added and stirred for 30 min, the stirred mixture was cooled to room temperature, the organic layer was extracted with DCM, and after concentration, intermediate 5-b (0.23 g, yield: 35%) was isolated and purified by column chromatography.

[0113] 5.3 Synthesis of intermediate 5-c: A 250 mL two-necked flask was charged with 1-bromo-2,6-dichlorobenzene (2.26 g, 10 mmol), deuterated 3,6-di-tert-butylcarbazole (2.85 g, 10 mmol), potassium carbonate (2.76 g, 20 mmol), and purged with argon three times, then dry dimethyl sulfoxide (20 mL) was added, and then reacted at 150°C for 24 h. After the reaction was cooled to room temperature, it was extracted with DCM three times, and then the excess solvent was removed using a rotary evaporator, and then intermediate 5-c (3.5 g, 7.5 mmol, yield 75%) was isolated and purified by column chromatography.

[0114] 5.4 Synthesis of intermediate 5-d: A 250 mL two-necked flask was charged with intermediate 5-c (470 mg, 1 mmol), intermediate 5-b (525 mg, 1 mmol), anhydrous potassium carbonate (414 mg, 3 mmol), and purged with argon three times, then dry dimethyl sulfoxide (20 mL) was added, and then reacted at 150°C for 24 h. After the reaction was cooled to room temperature, it was extracted with DCM three times, and then the excess solvent was removed using a rotary evaporator, and then intermediate 5-d (673 mg, yield 70%) was isolated and purified by column chromatography.

[0115] 5.5 Synthesis of target compound 5: A 100 mL two-necked flask was charged with intermediate 5-d (480 mg, 0.5 mmol), m-xylene 10 mL, and then n-butyllithium in n-hexane solution (0.2 mL, 1M, 0.51 mmol) was added dropwise to the reaction system at -40°C and stirred for 1 h. Then after dropwise addition of boron tribromide (188 mg, 0.75 mmol) at -78°C, it was stirred at room temperature for 1 h, and then after dropwise addition of N,N-diisopropylethylamine (100 mg, 0.75 mmol) at 0°C, it was heated and stirred at 150°C for 24 h. After cooling to room temperature, the organic layer was extracted with DCM, and after concentration, target compound 5 (204 mg, 0.23 mmol, yield 46%) was isolated and purified by column chromatography.

[0116] Example 6

[0117] The synthesis route of target compound 6 of the present example is as follows:

[0118] Synthesis steps:

[0119] 6.1 Synthesis of Intermediate 6-a: In a 1000 mL reaction flask was added 2,3- dibromocarbazole (19.5 g, 60 mmol), 3,6-di-tert-butylcarbazole (16.74 g, 60 mmol), cesium carbonate (21.2 g, 65 mmol), purged with argon three times, added N,N- dimethylformamide (700 mL), and reacted at 110 °C for 36 h. After the reaction was allowed to cool to room temperature, it was extracted three times with DCM, the excess solvent was removed using a rotary evaporator, and the product was purified by column chromatography to yield Intermediate 6-a (23.5 g, 45 mmol, 75% yield).

[0120] 6.2 Synthesis of Intermediate 6-b: In a 1000 mL reaction flask was added Intermediate 6-a (23.5 g, 45 mmol), phenoxazine (9.15 g, 50 mmol), palladium acetate (600 mg, 2.5 mmol), tri-tert-butylphosphonium tetrafluoroborate (1.41 g, 5 mmol), sodium tert-butoxide (5.76 g, 60 mmol), purged with argon three times, added anhydrous toluene (200 mL), and reacted at 110 °C for 36 h. After the reaction was allowed to cool to room temperature, it was extracted three times with DCM, the excess solvent was removed using a rotary evaporator, and the product was purified by column chromatography to yield Intermediate 6-b (22 g, 80% yield).

[0121] 6.3 Synthesis of Intermediate 6-c: In a 500 mL two-necked flask was added Intermediate 6-b (22 g, 36 mmol), palladium acetate (807 mg, 3.6 mmol), silver oxide (16.71 g, 72 mmol), purged with argon three times, added pivalic acid (360 mL), reacted at 150 °C for 6 h, added anhydrous potassium carbonate (1.65 g, 12 mmol), and reacted for an additional 12 h. After the reaction was allowed to cool to room temperature, saturated aqueous sodium bicarbonate was added and stirred, the organic layer was extracted with DCM, concentrated, and purified by column chromatography to yield Intermediate 6-c (11.2 g, 18 mmol, 50% yield).

[0122] 6.4 Synthesis of intermediate 6-d: In a 500 mL two necked flask was added 1-bromo-2,6-dichlorobenzene (6.78 g, 30 mmol), phenothiazine (5.97 g, 30 mmol), tris(dibenzylideneacetone)dipalladium (2.76 g, 3 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl (1.23 g, 3 mmol), sodium tert-butoxide (3.6 g, 37.5 mmol) was purged with argon three times, dry toluene (300 mL) was added and then the reaction was heated at 110 °C for 24 h. After the reaction was cooled to room temperature, it was extracted with DCM three times and the excess solvent was removed using a rotary evaporator. The product was purified by column chromatography to obtain intermediate 6-d (8.4 g, 75% yield).

[0123] 6.5 Synthesis of intermediate 6-e: In a 500 mL two necked flask was added intermediate 6-d (8.4 g, 18 mmol), intermediate 6-c (11.2 g, 18 mmol), anhydrous potassium carbonate (2.76 g, 20 mmol) was purged with argon three times, dry dimethyl sulfoxide (150 mL) was added and then the reaction was heated at 150 °C for 48 h. After the reaction was cooled to room temperature, it was extracted with DCM three times and the excess solvent was removed using a rotary evaporator. The product was purified by column chromatography to obtain intermediate 6-e (22.14 g, 80% yield).

[0124] 6.6 Synthesis of target compound 6: In a 500 mL reaction flask was added intermediate 6-e (22.1 g, 14 mmol), p-xylene 280 mL, n-butyllithium in hexane (5.6 mL, 7.3 mol / L, 14.28 mmol) was added drop wise to the reaction mixture at -40 °C and stirred for 1 h. Then boron tribromide (5 g, 20 mmol) was added drop wise at -78 °C and stirred at room temperature for 1 h. N,N-diisopropylethylamine (2.58 g, 20 mmol) was added drop wise at 0 °C and heated at 150 °C for 24 h. After cooling to room temperature, the organic layer was extracted with DCM, concentrated and purified by column chromatography to obtain target compound 6 (6.4 g, 7.1 mmol, 45% yield).

[0125] Example 7

[0126] The synthetic route of target compound 7 of this example is as follows:

[0127] Synthetic steps:

[0128] 7.1 Synthesis of Intermediate 7-a: In a 1000 mL reaction flask was added 2,3- dibromocarbazole (9.75 g, 30 mmol), 9,9-diphenyl-9,10-dihydroacridine (23.34 g, 70 mmol), palladium acetate (720 mg, 3 mmol), tri-tert-butylphosphonium tetrafluoroborate (1.69 g, 6 mmol), sodium tert-butoxide (6.72 g, 70 mmol), purged with argon three times, added anhydrous toluene (400 mL), then reacted at 110 °C for 48 h. After the reaction was reduced to room temperature, extracted with DCM three times, removed the excess solvent with a rotary evaporator, then purified by column chromatography to obtain Intermediate 7-a (17.4 g, 21 mmol, yield 70%).

[0129] 7.2 Synthesis of Intermediate 7-b: In a 500 mL two-neck flask was added Intermediate 7-a (17.4 g, 21 mmol), palladium acetate (471 mg, 2.1 mmol), silver oxide (9.75 g, 42 mmol), purged with argon three times, added pivalic acid (210 mL), reacted at 150 °C for 6 h, then added anhydrous potassium carbonate (973 mg, 7 mmol), continued to react for 12 h, after the reaction was reduced to room temperature, added saturated aqueous sodium bicarbonate solution and stirred, then extracted the organic layer with DCM, concentrated and purified by column chromatography to obtain Intermediate 7-b (8.25 g, 10 mmol, yield 48%).

[0130] 7.3 Synthesis of Intermediate 7-c: In a 500 mL two-neck flask was added 1- bromo-2,6-dichlorobenzene (4.52 g, 20 mmol), 9,9-diphenyl-9,10-dihydroacridine (5.97 g, 19 mmol), tris(dibenzylideneacetone)dipalladium (920 mg, 1 mmol), 2- dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl (410 mg, 1 mmol), sodium tert- butoxide (2.4 g, 25 mmol), purged with argon three times, added super dry toluene (300 mL), then reacted at 110 °C for 24 h. After the reaction was reduced to room temperature, extracted with DCM three times, removed the excess solvent with a rotary evaporator, then purified by column chromatography to obtain Intermediate 7-c (8.33 g, 16 mmol, yield 80%).

[0131] 7.4 Synthesis of intermediate 7-d: In a 500 mL two necked flask was added intermediate 7-c (5.21 g, 10 mmol), intermediate 7-b (8.25 g, 10 mmol), anhydrous potassium carbonate (2.1 g, 15 mmol), purged with argon three times, added dry dimethylsulfoxide (100 mL), then reacted at 150 °C for 36 h. After the reaction was cooled to room temperature, extracted with DCM three times, then removed the excess solvent using a rotary evaporator, and then purified by column chromatography to obtain intermediate 7-d (9.17 g, 7 mmol, yield 70%).

[0132] 7.5 Synthesis of target compound 7: In a 500 mL two necked flask was added intermediate 7-d (9.17 g, 7 mmol), p-xylene 140 mL, added n-butyllithium in n-hexane solution (2.8 mL, 3.6 M, 7.14 mmol) dropwise to the reaction system at -40 °C and stirred for 1 h. Then after adding boron tribromide (2.5 g, 10 mmol) dropwise at -78 °C, stirred at room temperature for 1 h, then added N,N-diisopropylethylamine (1.27 g, 10 mmol) dropwise at 0 °C and heated and stirred at 150 °C for 24 h. Cooled to room temperature, extracted the organic layer with DCM, concentrated, and then purified by column chromatography to obtain the product target compound 7 (3.7 g, 3 mmol, yield 43%).

[0133] Example 8

[0134] The synthesis route of the target compound 8 of the present example is as follows:

[0135] Synthesis steps:

[0136] 8.1 Synthesis of intermediate 8-a: In a 1000 mL two necked flask was added 4-bromo-3,5-dichlorobenzonitrile (12.5 g, 50 mmol), 2,4-dibromocarbazole (19.5 g, 60 mmol), anhydrous potassium carbonate (9.66 g, 70 mmol), purged with argon three times, added dry dimethylsulfoxide (150 mL), then reacted at 150 °C for 48 h. After the reaction was cooled to room temperature, extracted with dichloromethane (DCM) (300 mL x 3) three times, then removed the excess solvent using a rotary evaporator, and then purified by column chromatography to obtain intermediate 8-a (20.36 g, yield 76%).

[0137] 8.2 Synthesis of Intermediate 8-b: In a 1000 mL two-necked flask, Intermediate 1-a (16.1 g, 30 mmol), 9H-pyrido[3,4-b]indole (5.55 g, 33 mmol), tris(dibenzylideneacetone)dipalladium (1.37 g, 1.5 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl (1.23 g, 3 mmol), sodium tert-butoxide (3.84 g, 40 mmol) were purged with argon for three times, dry toluene (300 mL) was added, then the reaction was carried out at 110 °C for 48 h. After the reaction was cooled to room temperature, it was extracted with dichloromethane (DCM) (300 mL x 3) for three times, then the excess solvent was removed by rotary evaporator, and the product was purified by column chromatography to give Intermediate 8-b (14 g, yield 70%).

[0138] 8.3 Synthesis of Intermediate 8-c: In a 500 mL flask, Intermediate 8-b (13.4 g, 20 mmol), m-xylene 200 mL were added, n-butyllithium in n-hexane (8.2 mL, 2.5 M, 20.4 mmol) was added dropwise to the reaction system at -78 °C and stirred for 1 h, then heated and stirred at 60 °C for 2 h, and then the low boiling point solvent was removed by distillation under reduced pressure. After adding boron tribromide (5.64 g, 22.4 mmol) dropwise at -78 °C, stirring at room temperature for 1 h, adding N,N-diisopropylethylamine (2.96 g, 22.4 mmol) dropwise at 0 °C, and heating and stirring at 140 °C for 24 h. After cooling to room temperature, sodium acetate aqueous solution was added and stirred, the organic layer was extracted with DCM, concentrated and purified by column chromatography to give Intermediate 8-c (4.9 g, 8.2 mmol, yield 40%).

[0139] 8.4 Synthesis of Intermediate 8-d: In a 500 mL two-necked flask, Intermediate 8-c (3 g, 5 mmol), 2,3-benzocarbazole (1.3 g, 6 mmol), palladium acetate (56 mg, 0.25 mmol), tri-tert-butylphosphine tetrafluoroborate (145 mg, 0.5 mmol), sodium tert-butoxide (960 mg, 10 mmol) were purged with argon for three times, dry toluene (50 mL) was added, then the reaction was carried out at 110 °C for 36 h. After the reaction was cooled to room temperature, it was extracted with dichloromethane (100 mL x 3) for three times, then the excess solvent was removed by rotary evaporator, and the product was purified by column chromatography to give Intermediate 8-d (3 g, yield 70%).

[0140] 8.5 Synthesis of target compound 8: In a 200 mL flask, intermediate 8-d (4.36 g, 5 mmol), palladium acetate (112 mg, 0.5 mmol), silver oxide (2.31 g, 10 mmol) were added, purged with argon three times, t-amyl alcohol (50 mL) was added, after reaction at 150 °C for 6 h, anhydrous potassium carbonate (135 mg, 1 mmol) was added, and the reaction was continued for 12 h, after the reaction was cooled to room temperature, saturated aqueous sodium bicarbonate solution was added and stirred, then the organic layer was extracted with DCM, concentrated and purified by column chromatography to obtain target compound 8 (1.8 g, 2.1 mmol, yield 42%).

[0141] Example 9

[0142] The synthesis route of target compound 9 of this example is as follows:

[0143] Synthesis steps:

[0144] 9.1 Synthesis of intermediate 9-a: In a 1000 mL flask, 2,3-dibromocarbazole (19.5 g, 60 mmol), 3,6-di-tert-butylcarbazole (16.74 g, 60 mmol), cesium carbonate (21.2 g, 65 mmol) were added, purged with argon three times, N,N-dimethylformamide (700 mL) was added, and the reaction was carried out at 110 °C for 36 h. After the reaction was cooled to room temperature, it was extracted with DCM three times, the excess solvent was removed by rotary evaporator, and then purified by column chromatography to obtain intermediate 9-a (23.5 g, yield 75%).

[0145] 9.2 Synthesis of intermediate 9-b: In a 1000 mL flask, intermediate 9-a (23.5 g, 45 mmol), 5-phenyl-5,11-dihydroindolo[3,2-B]carbazole (16.6 g, 50 mmol), palladium acetate (600 mg, 2.5 mmol), tri-tert-butylphosphine tetrafluoroborate (1.41 g, 5 mmol), sodium tert-butoxide (5.76 g, 60 mmol) were added, purged with argon three times, anhydrous toluene (400 mL) was added, and the reaction was carried out at 110 °C for 36 h. After the reaction was cooled to room temperature, it was extracted with DCM three times, the excess solvent was removed by rotary evaporator, and then purified by column chromatography to obtain intermediate 9-b (23.7 g, yield 68%).

[0146] 9.3 Synthesis of Intermediate 9-c: In a 500 mL two-necked flask was placed Intermediate 9-b (23.2 g, 30 mmol), palladium acetate (672 mg, 3 mmol), silver oxide (13.9 g, 60 mmol), purged with argon three times, added pivalic acid (360 mL), after reaction at 150 °C for 6 h, added anhydrous potassium carbonate (1.38 g, 10 mmol), continued to react for 12 h, after the reaction was reduced to room temperature, added saturated aqueous sodium bicarbonate solution and stirred, then extracted the organic layer with DCM, concentrated and purified by column chromatography to obtain Intermediate 9-c (9.9 g, 12.9 mmol, yield 43%).

[0147] 9.4 Synthesis of Intermediate 9-d: In a 500 mL two-necked flask was placed 4-bromo-3,5-dichlorobenzotrifluoride (5.88 g, 20 mmol), benzo[b][l,8]naphthyridine (4.63 g, 22 mmol), tris(dibenzylideneacetone)dipalladium (1.83 g, 2 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-l,l'- biphenyl (821 mg, 2 mmol), sodium tert-butoxide (2.4 g, 25 mmol), purged with argon three times, added super dry toluene (200 mL), then reacted at 110 °C for 24 h. After the reaction was reduced to room temperature, extracted with DCM three times, then removed the excess solvent with a rotary evaporator, and purified by column chromatography to obtain Intermediate 9-d (6.05 g, yield 65%).

[0148] 9.4 Synthesis of Intermediate 9-d: In a 500 mL two-necked flask was placed 4-bromo-3,5-dichlorobenzotrifluoride (5.88 g, 20 mmol), benzo[b][l,8]naphthyridine (4.63 g, 22 mmol), tris(dibenzylideneacetone)dipalladium (1.83 g, 2 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-l,l'- biphenyl (821 mg, 2 mmol), sodium tert-butoxide (2.4 g, 25 mmol), purged with argon three times, added super dry toluene (200 mL), then reacted at 110 °C for 24 h. After the reaction was reduced to room temperature, extracted with DCM three times, then removed the excess solvent with a rotary evaporator, and purified by column chromatography to obtain Intermediate 9-d (6.05 g, yield 65%).

[0149] 9.4 Synthesis of target compound 9: To a 500 mL reaction flask was added intermediate 9-e (10.8 g, 9 mmol), p-xylene 90 mL, n-butyllithium in n-hexane (3.7 mL, 9.18 mmol) was added dropwise to the reaction mixture at -40 °C and stirred for 1 h. Then after dropwise addition of boron tribromide (2.7 g, 10.8 mmol) at -78 °C, it was stirred at room temperature for 1 h, and after dropwise addition of N,N-diisopropylethylamine (1.39 g, 10.8 mmol) at 0 °C, it was stirred at 150 °C for 24 h. After cooling to room temperature, the organic layer was extracted with DCM, and after concentration, the product target compound 9 (3.9 g, 3.5 mmol, 38% yield) was isolated and purified by column chromatography.

[0150] Example 10

[0151] The synthetic route of the target compound 10 of the present example is as follows:

[0152] Synthetic steps:

[0153] 10.1 Synthesis of intermediate 10-a: To a 1000 mL reaction flask was added 2,3- dibromocarbazole (9.75 g, 30 mmol), 9,9-diphenyl-9,10-dihydroacridine (11.67 g, 35 mmol), palladium acetate (360 mg, 1.5 mmol), tri-tert-butylphosphonium tetrafluoroborate (845 mg, 3 mmol), sodium tert-butoxide (3.84 g, 40 mmol), and purged with argon three times, and then anhydrous toluene (400 mL) was added, and then it was reacted at 110 °C for 48 h. After the reaction was cooled to room temperature, it was extracted with DCM three times, and after removing the excess solvent with a rotary evaporator, intermediate 10-a (11.9 g, 20.5 mmol, 68% yield) was isolated and purified by column chromatography.

[0154] 10.2 Synthesis of intermediate 10-b: To a 500 mL reaction flask was added intermediate 10-a (11.5 g, 20 mmol), 6,6-dimethyl-6,11-dihydro-13-oxa-11- azacarbazole [1,2-b] anthracene (6.59 g, 22 mmol), palladium acetate (225 mg, 1 mmol), tri-tert-butylphosphonium tetrafluoroborate (564 mg, 2 mmol), sodium tert-butoxide (2.30 g, 24 mmol), and purged with argon three times, and then anhydrous toluene (200 mL) was added, and then it was reacted at 110 °C for 36 h. After the reaction was cooled to room temperature, it was extracted with DCM three times, and after removing the excess solvent with a rotary evaporator, intermediate 10-b (10.3 g, 13 mmol, 65% yield) was isolated and purified by column chromatography.

[0155] 10.3 Synthesis of Intermediate 10-c: In a 500 mL two necked flask was added Intermediate 10-b (8 g, 10 mmol), palladium acetate (225 mg, 1 mmol), silver oxide (4.64 g, 20 mmol), purged with argon three times, added super dry pivalic acid (100 mL), after 6 h of reaction at 150 °C, added anhydrous potassium carbonate (690 mg, 5 mmol), continued the reaction for 12 h, after the reaction was brought to room temperature, added saturated aqueous sodium bicarbonate solution and stirred, then extracted the organic layer with DCM, concentrated and purified by column chromatography to get Intermediate 10-c (3.72 g, 4.7 mmol, 47% yield).

[0156] 10.4 Synthesis of Intermediate 10-d: In a 500 mL two necked flask was added 4-bromo-3,5-dichlorobenzotrifluoride (2.94 g, 10 mmol), 4-methyl-10H- phenoxazine (1.35 g, 12 mmol), tris(dibenzylideneacetone)dipalladium (915 mg, 1 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl (410 mg, 1 mmol), sodium tert-butoxide (1.34 g, 14 mmol), purged with argon three times, added super dry toluene (100 mL), then reacted at 110 °C for 24 h. After the reaction was brought to room temperature, extracted with DCM three times, removed the excess solvent using a rotary evaporator, then purified by column chromatography to get Intermediate 10-d (2.69 g, 7 mmol, 70% yield).

[0157] 10.5 Synthesis of Intermediate 10-e: In a 500 mL two necked flask was added Intermediate 10-d (1.92 g, 5 mmol), Intermediate 10-c (4 g, 5 mmol), anhydrous potassium carbonate (828 mg, 6 mmol), purged with argon three times, added super dry dimethyl sulfoxide (50 mL), then reacted at 150 °C for 48 h. After the reaction was brought to room temperature, extracted with DCM three times, removed the excess solvent using a rotary evaporator, then purified by column chromatography to get Intermediate 10-e (4.16 g, 3.65 mmol, 73% yield).

[0158] 10.6 Synthesis of target compound 10: Into a 500 mL reaction flask, intermediate 10-e (10.8 g, 3 mmol) and p-xylene 30 mL were added, and n-butyllithium in n-hexane (1.22 mL, 3.06 mmol) was added dropwise into the reaction system at -40 °C and stirred for 1 h. Then after dropwise addition of boron tribromide (0.9 g, 3.6 mmol) at -78 °C, it was stirred at room temperature for 1 h, and after dropwise addition of N, N-diisopropylethylamine (465 mg, 3.6 mmol) at 0 °C, it was heated and stirred at 150 °C for 24 h. After cooling to room temperature, the organic layer was extracted with DCM, and after concentration, the product target compound 10 (1.08 g, 1 mmol, yield 35%) was separated and purified by column chromatography.

[0159] The Mass Spectrometry (MS) and Elemental Analysis (EA) results of the target compounds synthesized in Examples 1-10 and Compound A (structural formula is referred to below) are shown in Table 1 below.

[0160] Table 1

[0161] The performance of the electroluminescent devices including the above-mentioned compounds was tested by specific device Examples 1-20 and Comparative Examples 1-2 below. Among them, the schematic diagram of the film layer stack of the electroluminescent device is shown in Figure 1, wherein 1— glass and conductive glass (ITO anode) substrate layer; 2— hole injection layer (HATCN, 10 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 (DBFPO, 20 nm); 7— electron transport layer (ANT-BIZ, 30 nm); 8— electron injection layer (LiQ, 1 nm); 9— cathode (Al, 100 nm).

[0162] Among them, the device Examples 1-20 and the device Comparative Examples 1 are the same in device structure and manufacturing method except for the difference in the material of the light-emitting layer.

[0163] The light-emitting layer of device Comparative Example 1: Compound A and host light-emitting material mCBP, evaporation ratio 4:196.

[0164] The light-emitting layer of device Comparative Example 2: Compound A, photosensitizer Ir(ppy)3 and host light-emitting material mCBP, evaporation ratio 2:20:178.

[0165] The light-emitting layer of device Example 1: The difference from device Comparative Example 1 is that Compound A is replaced by Compound 1 synthesized in Example 1.

[0166] Light-emitting layer of Device Example 2: The difference from Device Comparative Example 1 is that Compound A is replaced with Compound 2 synthesized in Example 2.

[0167] Light-emitting layer of Device Example 3: The difference from Device Comparative Example 1 is that Compound A is replaced with Compound 3 synthesized in Example 3.

[0168] Light-emitting layer of Device Example 4: The difference from Device Comparative Example 1 is that Compound A is replaced with Compound 4 synthesized in Example 4.

[0169] Light-emitting layer of Device Example 5: The difference from Device Comparative Example 1 is that Compound A is replaced with Compound 5 synthesized in Example 5.

[0170] Light-emitting layer of Device Example 6: The difference from Device Comparative Example 1 is that Compound A is replaced with Compound 6 synthesized in Example 6.

[0171] Light-emitting layer of Device Example 7: The difference from Device Comparative Example 1 is that Compound A is replaced with Compound 7 synthesized in Example 7.

[0172] Light-emitting layer of Device Example 8: The difference from Device Comparative Example 1 is that Compound A is replaced with Compound 8 synthesized in Example 8.

[0173] Light-emitting layer of Device Example 9: The difference from Device Comparative Example 1 is that Compound A is replaced with Compound 9 synthesized in Example 9.

[0174] Light-emitting layer of Device Example 10: The difference from Device Comparative Example 1 is that Compound A is replaced with Compound 10 synthesized in Example 10.

[0175] Light-emitting layer of Device Example 11: The difference from Device Comparative Example 2 is that Compound A is replaced with Compound 1 synthesized in Example 1.

[0176] Light-emitting layer of Device Example 12: The difference from Device Comparative Example 2 is that Compound A is replaced with Compound 2 synthesized in Example 2.

[0177] Light-emitting layer of Device Example 13: The difference from Device Comparative Example 2 is that Compound A is replaced with Compound 3 synthesized in Example 3.

[0178] Light-emitting layer of Device Example 14: The difference from Device Comparative Example 2 is that Compound A is replaced with Compound 4 synthesized in Example 4.

[0179] Light-emitting layer of Device Example 15: The difference from Device Comparative Example 2 is that Compound A is replaced with Compound 5 synthesized in Example 5.

[0180] Light-emitting layer of device example 16: The difference from device comparative example 2 is that compound A is replaced by compound 6 synthesized in example 6.

[0181] Light-emitting layer of device example 17: The difference from device comparative example 2 is that compound A is replaced by compound 7 synthesized in example 7.

[0182] Light-emitting layer of device example 18: The difference from device comparative example 2 is that compound A is replaced by compound 8 synthesized in example 8.

[0183] Light-emitting layer of device example 19: The difference from device comparative example 1 is that compound A is replaced by compound 9 synthesized in example 9.

[0184] Light-emitting layer of device example 20: The difference from device comparative example 2 is that compound A is replaced by compound 10 synthesized in example 10.

[0185] 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 1 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

[0186] Table 2

[0187] As can be seen from Table 2, compared with the electroluminescent device prepared in device comparative example 1, the electroluminescent devices prepared in device examples 1-10 provided by the present application have lower operating voltage, higher luminescent efficiency and higher service life. The possible reason is that the compound provided by the present application, by introducing a bulky heterocyclic aromatic fragment, makes the molecule present a certain degree of twisted structure, which can effectively inhibit the concentration quenching effect, and by introducing heteroatoms such as oxygen and sulfur, it is beneficial to enhance the spin-orbit coupling effect of the molecule, so that the molecule has a short delay lifetime, thereby improving the luminescent efficiency and service life of the device as a whole.

[0188] Compared with the electroluminescent devices prepared in device examples 1-10, the electroluminescent devices prepared in device examples 11-20 can further reduce the operating voltage, improve the luminous efficiency and prolong the service life. The possible reason is that by introducing phosphorescent material into the light-emitting layer, the high-efficiency phosphorescent material can capture the triplet excitons in the electroluminescent device in combination with the compound provided in the embodiments of the present application, and transfer the energy to the fluorescent molecules (the compound provided in the present application) by energy transfer to make the fluorescent molecules emit light, thereby realizing the utilization of high-efficiency triplet excitons while maintaining the narrow spectrum of the fluorescent molecules, and further realizing the electroluminescent device with high efficiency, high color purity and high stability.

[0189] In the above embodiments, the description of each embodiment has its own focus, and the parts not described in detail in a certain embodiment can be referred to the relevant description of other embodiments.

[0190] The boron-containing compounds, electroluminescent devices and display panels provided in the embodiments of the present application are described in detail above, and the above description is only used to help understand the technical solutions and core ideas of the present application; the modification of the technical solutions recorded in the foregoing embodiments or the equivalent replacement of part of the technical features does not make 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 boron-containing compound of the formula: ###0001### wherein, The structural general formula of the boron-containing compound is shown as formula (I): each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10heteroaryl; 60 each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10heteroaryl; 60 each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10hetero R1, R2, and R3 are each independently selected from hydrogen atoms, deuterium atoms, halogen atoms, -CN, -NO2, -CF3, -OH, -SH, -NH2, C1-C 30 Straight chain hydrocarbon, C3-C 30 Branched hydrocarbon groups, C3-C 30 Cycloalkyl, C1-C 30 Alkoxy, C1-C 30 Alkylthio, C6-C 60 Aryl, C6-C 60 Aryl ether group, C5-C 60 Heteroaryl or C5-C 60 Heteroaryl ether group; R is, at each occurrence, independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -NR4-, -POR4-, -0-, -S-, -Se-, -Te-, -SO-, or -SO2-; R4and R5are each independently selected from H, C1-C 30 alkyl, or C6-C 30 aryl; G is selected from a nitrogen atom or a phosphinoyl group; X, Y, Z are each independently selected from a carbon atom or a nitrogen atom.

2. The boron-containing compound of claim 1, wherein, selected from any one of the following structures: wherein "*" represents a connecting site; R 1 each occurrence is independently selected from H, substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C1-C6alkyl; 40 each occurrence is independently selected from H, substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C1-C6alkyl; or unsubstituted C5-C 40 heteroaryl; and / or, adjacent R 1 groups form a ring or are not annelated.

3. The boron-containing compound of claim 1, wherein, The structural general formula of the boron-containing compound is shown as formula (I-1) or formula (I-2): To each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted 5- to 10-membered heteroaryl; 30 each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted 5- to 10-membered heteroaryl; 30 each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted R1, R2, and R3 are each independently selected from hydrogen atoms, deuterium atoms, halogen atoms, -CN, -NO2, -CF3, -OH, -SH, -NH2, C1-C 30 Straight chain hydrocarbon, C3-C 30 Branched hydrocarbon groups, C3-C 30 Cycloalkyl, C1-C 30 Alkoxy, C1-C 30 Alkylthio, C6-C 60 Aryl, C6-C 60 Aryl ether group, C5-C 60 Heteroaryl or C5-C 60 Heteroaryl ether group; R is, at each occurrence, independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -NR4-, -POR4-, -0-, -S-, -Se-, -Te-, -SO-, or -SO2-; R4and R5are each independently selected from H, C1-C 30 alkyl, or C6-C 30 aryl.

4. The boron-containing compound of claim 3, wherein, The structural general formula of the boron-containing compound is shown as formula (I-1-1) or formula (I-2-1): To each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10heteroaryl; 30 each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10heteroaryl; 30 each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10hetero R1, R2, and R3 are each independently selected from hydrogen atoms, deuterium atoms, halogen atoms, -CN, -NO2, -CF3, -OH, -SH, -NH2, C1-C 30 Straight chain hydrocarbon, C3-C 30 Branched hydrocarbon groups, C3-C 30 Cycloalkyl, C1-C 30 Alkoxy, C1-C 30 Alkylthio, C6-C 60 Aryl, C6-C 60 Aryl ether group, C5-C 60 Heteroaryl or C5-C 60 Heteroaryl ether group; R is, at each occurrence, independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -NR4-, -POR4-, -0-, -S-, -Se-, -Te-, -SO-, or -SO2-; R4and R5are each independently selected from H, C1-C 30 alkyl, or C6-C 30 aryl.

5. The boron-containing compound of claim 4, wherein, to each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted quinolizyl.

6. The boron-containing compound of claim 5, wherein, to each independently selected from a phenyl group, a benzothiophene group, a biphenyl group, a naphthalene group, a quinazoline group, a carbazole group substituted with a phenyl group, or a dibenzofuran group, substituted or unsubstituted with a deuterium atom, -CH3, -C(CH3)3, -CF3, -CN, or -OCH3.

7. The boron-containing compound of claim 4, wherein, R1, R2, R3 are each independently selected from a hydrogen atom, -CN, -CF3 or -OCH3.

8. The boron-containing compound of claim 4, wherein, R is, at each occurrence, independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -O-, -S-, -Se-, -Te-, -SO-, or -SO2-, each R4and R5is independently selected from H, C1-C6alkyl, or C6-C10aryl. 10 20 C6-C10aryl.​ 9. The boron-containing compound of claim 4, wherein, The boron-containing compound is selected from one of the following compounds of the following structural formula:

10. An electroluminescent device, wherein, An anode and a cathode, and a light-emitting layer between the anode and the cathode, the light-emitting layer comprising a boron-containing compound, wherein the compound has a general structure as shown in formula (I): each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10heteroaryl; 60 each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10heteroaryl; 60 each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10hetero R1, R2, and R3 are each independently selected from hydrogen atoms, deuterium atoms, halogen atoms, -CN, -NO2, -CF3, -OH, -SH, -NH2, C1-C 30 Straight chain hydrocarbon, C3-C 30 Branched hydrocarbon groups, C3-C 30 Cycloalkyl, C1-C 30 Alkoxy, C1-C 30 Alkylthio, C6-C 60 Aryl, C6-C 60 Aryl ether group, C5-C 60 Heteroaryl or C5-C 60 Heteroaryl ether group; R is, at each occurrence, independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -NR4-, -POR4-, -0-, -S-, -Se-, -Te-, -SO-, or -SO2-; R4and R5are each independently selected from H, C1-C 30 alkyl, or C6-C 30 aryl; G is selected from a nitrogen atom or a phosphinoyl group; X, Y, Z are each independently selected from a carbon atom or a nitrogen atom.

11. The electroluminescent device according to claim 10, wherein, selected from any one of the following structures: wherein "*" represents a connecting site; R 1 each occurrence is independently selected from H, substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10heteroaryl; and / or, adjacent R 40 form a ring or do not form a ring. 40 each occurrence is independently selected from H, substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10heteroaryl; and / or, adjacent R 1 form a ring or do not form a ring.

12. The electroluminescent device according to claim 10, wherein, The structural general formula of the boron-containing compound is shown as formula (I-1) or formula (I-2): To each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted 5- to 10-membered heteroaryl; 30 each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted 5- to 10-membered heteroaryl; 30 each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted R1, R2, and R3 are each independently selected from hydrogen atoms, deuterium atoms, halogen atoms, -CN, -NO2, -CF3, -OH, -SH, -NH2, C1-C 30 Straight chain hydrocarbon, C3-C 30 Branched hydrocarbon groups, C3-C 30 Cycloalkyl, C1-C 30 Alkoxy, C1-C 30 Alkylthio, C6-C 60 Aryl, C6-C 60 Aryl ether group, C5-C 60 Heteroaryl or C5-C 60 Heteroaryl ether group; R is, at each occurrence, independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -NR4-, -POR4-, -0-, -S-, -Se-, -Te-, -SO-, or -SO2-; R4and R5are each independently selected from H, C1-C 30 alkyl, or C6-C 30 aryl.

13. The electroluminescent device according to claim 12, wherein, The structural general formula of the boron-containing compound is shown as formula (I-1-1) or formula (I-2-1): To each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10heteroaryl; 30 each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10heteroaryl; 30 each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10hetero R1, R2, and R3 are each independently selected from hydrogen atoms, deuterium atoms, halogen atoms, -CN, -NO2, -CF3, -OH, -SH, -NH2, C1-C 30 Straight chain hydrocarbon, C3-C 30 Branched hydrocarbon groups, C3-C 30 Cycloalkyl, C1-C 30 Alkoxy, C1-C 30 Alkylthio, C6-C 60 Aryl, C6-C 60 Aryl ether group, C5-C 60 Heteroaryl or C5-C 60 Heteroaryl ether group; R is, at each occurrence, independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -NR4-, -POR4-, -0-, -S-, -Se-, -Te-, -SO-, or -SO2-; R4and R5are each independently selected from H, C1-C 30 alkyl, or C6-C 30 aryl.

14. The electroluminescent device according to claim 13, wherein, to each independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzofuranyl, substituted or unsubstituted biphenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted indolyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted quinolizyl.

15. An electroluminescent device as claimed in claim 14, wherein, to each independently selected from phenyl, benzothiophene, biphenyl, naphthyl, quinazoline, carbazole substituted with phenyl, or dibenzofurane, substituted or unsubstituted with a deuterium atom, -CH3, -C(CH3)3, -CF3, -CN, or -OCH3.

16. The electroluminescent device of claim 13, wherein, R1, R2, R3 are each independently selected from a hydrogen atom, -CN, -CF3 or -OCH3.

17. The electroluminescent device of claim 13, wherein, R is, at each occurrence, independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -O-, -S-, -Se-, -Te-, -SO-, or -SO2-, R4and R5are each independently selected from H, C1-C 10 alkyl, or C6-C 20 aryl.

18. The electroluminescent device of claim 13, wherein, The boron-containing compound is selected from one of the following compounds of the following structural formula:

19. A display panel, wherein, The display panel comprises an electroluminescent device comprising a boron-containing compound, wherein a general structural formula of the boron-containing compound is shown as formula (I): each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10heteroaryl; 60 each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10heteroaryl; 60 each independently selected from substituted or unsubstituted C6-C10aryl, or substituted or unsubstituted C5-C10hetero R1, R2, and R3 are each independently selected from hydrogen atoms, deuterium atoms, halogen atoms, -CN, -NO2, -CF3, -OH, -SH, -NH2, C1-C 30 Straight chain hydrocarbon, C3-C 30 Branched hydrocarbon groups, C3-C 30 Cycloalkyl, C1-C 30 Alkoxy, C1-C 30 Alkylthio, C6-C 60 Aryl, C6-C 60 Aryl ether group, C5-C 60 Heteroaryl or C5-C 60 Heteroaryl ether group; R is, at each occurrence, independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -NR4-, -POR4-, -0-, -S-, -Se-, -Te-, -SO-, or -SO2-; R4and R5are each independently selected from H, C1-C 30 alkyl, or C6-C 30 aryl; G is selected from a nitrogen atom or a phosphinoyl group; X, Y, Z are each independently selected from a carbon atom or a nitrogen atom.

20. The display panel of claim 19, wherein, The display panel further comprises a pixel driving circuit, which is electrically connected with the electroluminescent device.

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