Boron-containing compounds, electroluminescent devices and display panels

Abstract

The embodiments of the present application disclose a boron-containing compound, an electroluminescent device, and a display panel. The boron-containing compound has the general structural formula: #imgabs0##imgabs1# to #imgabs2# are each independently selected from substituted or unsubstituted aryl or heteroaryl groups, and R1 to R3 are selected from hydrogen, deuterium, halogen, CN, NO2, CF3, OH, SH, NH2, straight-chain hydrocarbon groups, branched hydrocarbon groups, cycloalkyl groups, alkoxy groups, alkylthio groups, C6-C 60 The boron-containing compounds provided in the embodiments of the present application can effectively suppress the concentration quenching effect and enhance the spin-orbit coupling effect of the molecule. The electroluminescent devices and display panels based on the boron-containing compounds have higher luminous efficiency and good device life.

Description

Technical Field

[0001] The present application relates to the technical field of organic optoelectronic materials, and in particular to a boron-containing compound, an electroluminescent device, and a display panel. Background Art

[0002] Organic light-emitting diodes (OLEDs) offer broad application prospects in flexible displays and solid-state lighting due to their advantages, including self-luminescence, high contrast, wide viewing angle, high luminous efficiency, fast response time, thinness, and foldability. The core of OLEDs is the guest luminescent material. These materials have evolved through three generations, from traditional fluorescent materials to phosphorescent materials and, more recently, thermally activated delayed fluorescence (TADF) materials. Under electrical excitation, the ratio of singlet excitons to triplet excitons is 1:3. In fluorescent materials, triplet excitons are transition-forbidden, so fluorescent materials can only utilize the 25% singlet exciton ratio. Consequently, the efficiency of corresponding electroluminescent devices rarely exceeds 5%. Phosphorescent materials exploit the spin-orbit coupling of heavy metal atoms and can utilize the radiative transition of triplet excitons to emit light. However, blue phosphorescent materials suffer from poor stability and are unable to achieve deep blue emission. Thermally activated delayed fluorescence materials are a class of materials with a small single-triplet energy level difference. They enable triplet excitons to reach the excited singlet state through a reverse intersystem crossing (RISC) process, and then radiatively transition to emit light, realizing the utilization of triplet excitons. However, most of these materials have a short lifetime, and the half-width of the luminescence peak is wide, resulting in low color purity of the luminescence, which cannot meet the needs of industrial applications.

[0003] Based on the above defects, luminescent materials with high luminous efficiency, high luminous color purity and long luminous life need to be developed. Summary of the Invention

[0004] The embodiments of the present application provide a boron-containing compound, an electroluminescent device, and a display panel to solve the problem that the luminous efficiency, luminous color purity, and lifespan of existing luminescent materials need to be improved.

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

[0006] The present invention provides a boron-containing compound, the general structural formula of which is shown in Formula (I):

[0007]

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

[0009] R1, R2, R3 are each independently selected from hydrogen atom, deuterium atom, halogen atom, CN, NO2,

[0010] 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 groups;

[0011] Each occurrence of R is independently selected from a single bond, CR4R5, CO, SiR4R5, NR4, POR4, O, S, Se, -Te-, SO or SO2; R4 and R5 are independently selected from H, C1-C 30 Alkyl, or C6-C 30 aryl groups;

[0012] G is selected from a nitrogen atom or a phosphino group;

[0013] X, Y, and Z are each independently selected from a carbon atom or a nitrogen atom.

[0014] In some embodiments of the present application, Select any one of the following structures:

[0015]

[0016] Among them, “*” indicates the connection site;

[0017] R 1 Each occurrence is independently selected from H, substituted or unsubstituted C6-C 40 aryl, or substituted or unsubstituted C5-C 40 and / or, adjacent R 1 There may be a ring or no ring between them.

[0018] In some embodiments of the present application, the general structural formula of the boron-containing compound is as shown in Formula (I-1) or Formula (I-2):

[0019]

[0020] Each independently selected from substituted or unsubstituted C6-C 30 aryl, or substituted or unsubstituted C6-C 30 heteroaryl;

[0021] 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 groups;

[0022] Each occurrence of R is independently selected from a single bond, CR4R5, CO, SiR4R5, NR4, POR4, O, S, Se, -Te-, SO or SO2; R4 and R5 are each independently selected from H, C1-C 30 Alkyl or C6-C 30 of aromatic groups.

[0023] In some embodiments of the present application, the general structural formula of the compound is as shown in Formula (I-1-1) or Formula (I-2-1):

[0024]

[0025] Each independently selected from substituted or unsubstituted C6-C 30 aryl, or substituted or unsubstituted C5-C 30 heteroaryl;

[0026] 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 groups;

[0027] Each occurrence of R is independently selected from a single bond, CR4R5, CO, SiR4R5, NR4, POR4, O, S, Se, -Te-, SO or SO2; R4 and R5 are each independently selected from H, C1-C 30 Alkyl or C6-C 30 of aromatic groups.

[0028] In some embodiments of the present application, Each is independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted indolyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted quinazolinyl group.

[0029] In some embodiments of the present application, Each is independently selected from a phenyl group which is substituted or unsubstituted by a deuterium atom, -CH3, -C(CH3)3, -CF3, -CN or -OCH3, a benzothiophene group, a biphenyl group, a naphthyl group, a quinazoline group, a carbazole group substituted by benzene or a dibenzofuran group.

[0030] In some embodiments of the present application, R1, R2, and R3 are each independently selected from a hydrogen atom, CN, CF3, or -OCH3.

[0031] In some embodiments of the present application, each occurrence of R is independently selected from a single bond, CR4R5, CO, SiR4R5, O, S, Se, -Te-, SO or SO2, and R4 and R5 are each independently selected from H, C1-C 10 Alkyl or C6-C 20 of aromatic groups.

[0032] In some embodiments of the present application, the boron-containing compound is selected from at least one of the compounds represented by the following structural formulas:

[0033]

[0034]

[0035]

[0036] The embodiments of the present application further provide an electroluminescent device, comprising an anode and a cathode, and a light-emitting layer located between the anode and the cathode, wherein the light-emitting layer comprises the boron-containing compound according to any of the above embodiments.

[0037] An embodiment of the present application further provides a display panel, comprising the boron-containing compound in any of the above embodiments or the electroluminescent device in any of the above embodiments.

[0038] The beneficial effects of the present application are as follows: The embodiments of the present application disclose a boron-containing compound, an electroluminescent device, and a display panel. The general structural formula of the boron-containing compound is: Selected from substituted C6-C 40 The aromatic rings, Each is independently selected from a substituted or unsubstituted aryl or heteroaryl group, R1 to R3 are selected from hydrogen, deuterium, halogen, CN, NO2, CF3, OH, SH, NH2, a straight-chain 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 phosphino group, and X, Y, and Z are selected from carbon or nitrogen. The boron-containing compounds provided in the embodiments of the present application introduce a large sterically hindered heterocyclic aromatic hydrocarbon fragment so that the molecule presents a certain degree of distorted structure, effectively suppressing 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 delayed life, which is beneficial to improving the efficiency roll-off problem of the device. The electroluminescent device and display panel based on the boron-containing compound have higher luminous efficiency and good device life. BRIEF DESCRIPTION OF THE DRAWINGS

[0039] Figure 1 Schematic diagram of the film stack structure of the electroluminescent device provided in an embodiment of the present application. DETAILED DESCRIPTION

[0040] This application provides a compound, an electroluminescent device, and a display panel. To clarify and clarify the objectives, technical solutions, and effects of this application, the application is further described below. It should be understood that the specific embodiments described herein are intended only to illustrate this application and are not intended to limit this application.

[0041] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as those commonly understood by those skilled in the art to which this application pertains. The terms used herein in the specification of this application are for the purpose of describing specific embodiments only and are not intended to limit this application. As used herein, "substituted" means that a hydrogen atom in a substituted group is replaced by a substituent.

[0042] In this application, "substituted or unsubstituted" means that the defined group may be substituted or unsubstituted. When the defined group is substituted, it is understood that the defined group may be substituted by one or more substituents R, wherein R is selected from but not limited to: deuterium, tritium, cyano, isocyano, nitro, halogen, alkyl 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", silane, carbonyl, alkoxycarbonyl, aryloxycarbonyl, Carbamoyl, haloformyl, formyl, isocyanate, thiocyanate, isothiocyanate, hydroxyl, trifluoromethyl, and the above groups may be further substituted by substituents acceptable in the art; it is understood that R' and R" in -NR'R" are independently selected from but not limited to: H, deuterium, tritium, cyano, isocyano, nitro or halogen, alkyl containing 1-10 carbon atoms, heterocyclic group containing 3-20 ring atoms, Aromatic group, 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, anthracenyl, pyrenyl, phenanthrenyl, pyridyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, naphthyridinyl, oxazolyl, benzoxazolyl, imidazolyl, benzimidazolyl, furyl, thienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, N-phenylcarbazolyl, 9,9-4-methylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl.

[0043] In this application, the number of atoms described by the numerical range includes both integer endpoints of the numerical range and each integer between 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 3-10 ring atoms" means containing 3, 4, 5, 6, 7, 8, 9 or 10 ring atoms.

[0044] In this application, the "number of ring atoms" refers to the number of atoms among the atoms constituting the ring itself of a structural compound (e.g., a monocyclic compound, a condensed ring compound, a cross-linked compound, a carbocyclic compound, a heterocyclic compound) in which atoms are bonded to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring atoms. The "number of ring atoms" described below is also the same 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 another example, the number of ring atoms of methylbenzene is 6.

[0045] "Aryl" or "aromatic group" refers to an aromatic hydrocarbon group derived from an aromatic ring compound by removing a hydrogen atom. It can be a monocyclic aromatic group, a condensed aromatic group, or a polycyclic aromatic group. For polycyclic rings, at least one is an aromatic ring system. For example, "substituted or unsubstituted C6-C 60 The term "aryl" refers to 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, and 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, anthracenyl, phenanthrenyl, fluoranthenyl, triphenylene, pyrenyl, The present invention also includes aryl, naphthyl, fluorenyl, perylene, acenaphthenyl and their derivatives. It is understood that multiple aromatic groups may also be interrupted by short non-aromatic units (e.g., <10% non-H atoms, such as C, N or O atoms), specifically acenaphthene, fluorene, or 9,9-diarylfluorene, triarylamine, diaryl ether system should also be included in the definition of aromatic group.

[0046] "Heteroaryl" or "heteroaromatic group" means that at least one carbon atom in an aromatic group is replaced by a non-carbon atom (heteroatom), which may be oxygen, sulfur, selenium, tellurium, nitrogen, etc. For example, "substituted or unsubstituted C5-C 60The term "heteroaryl" refers to a heteroaryl group having 5 to 60 carbon atoms, preferably a substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, more preferably a substituted or unsubstituted heteroaryl group having 5 to 18 carbon atoms, particularly preferably a substituted or unsubstituted heteroaryl group having 5 to 14 carbon atoms, and the heteroaryl group may be optionally further substituted. Suitable examples include, but are not limited to, thienyl, furyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, Pyridazinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothiophenyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothiphenyl, furopyrrolyl, furofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, o-naphthyl, phenanthridinyl, primary pyridyl, quinazolinone, dibenzothiophenyl, dibenzofuranyl, carbazolyl and derivatives thereof.

[0047] In the present application, "alkyl" can mean a straight chain, a branched chain and / or a cyclic alkyl group. The carbon number 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, tert-butyl, isobutyl, 2-ethylbutyl, 3,3-dimethylbutyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, cyclopentyl, 1-methylpentyl, 3-methylpentyl, 2-ethylpentyl, 4-methyl-2-pentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 2-butylhexyl, cyclohexyl, adamantyl, etc.

[0048] In the present application, the substituent abbreviations correspond to: n-normal, sec-secondary, i-iso, t-tertiary, o-ortho, m-meta, p-para, Me methyl, Et ethyl, Pr propyl, Bu butyl, Am n-pentyl, Hx hexyl, Cy cyclohexyl.

[0049] "Halogen" or "halogen atom" refers to F, Cl, Br or I.

[0050] The term "alkoxy" refers to a group having the structure "-O-alkyl", i.e., an alkyl group as defined above connected to another group via an oxygen atom. Suitable examples of phrases containing this term include, but are not limited to, methoxy (-O-CH or -OMe), ethoxy (-O-CHCH or -OEt), and tert-butoxy (-OC(CH) or -OtBu).

[0051] In this application, “further”, “further”, “particularly”, etc. are used for descriptive purposes to indicate differences in content, but should not be understood as limiting the scope of protection of the present invention.

[0052] In this application, the terms "optionally," "optional," and "optional" mean optional or dispensable, i.e., they refer to either option being selected from two parallel options: "with" or "without." If a technical solution contains multiple "optional" clauses, each "optional" clause is independent unless otherwise specified and there are no contradictions or constraints.

[0053] In this application, when describing each group, if the substitution is not emphasized, it is assumed that the group is unsubstituted. 30 "Alkyl" refers to an unsubstituted C1-C 30 Alkyl, "C6-C 60 "Aryl" refers to an unsubstituted C6-C 60 of aromatic groups.

[0054] In this application, the technical features described in an open manner include closed technical solutions composed of the listed features, and also include open technical solutions containing the listed features.

[0055] The general structural formula of the boron-containing compound provided in the embodiments of the present application is shown in the following formula (1):

[0056]

[0057] in, Selected from substituted or unsubstituted C6-C 60 aryl, or substituted or unsubstituted C5-C 60 of heteroaryl.

[0058] Each independently selected from substituted or unsubstituted C6-C 60 aryl, or substituted or unsubstituted C6-C 60 of heteroaryl.

[0059] 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.

[0060] Each occurrence of R is independently selected from a single bond, CR4R5, CO, SiR4R5, NR4, POR4, O, S, Se, -Te-, SO or SO2; R4 and R5 are each independently selected from H, C1-C 30 Alkyl or C6-C 30 of aromatic groups.

[0061] G is selected from a nitrogen atom or a phosphino group, and X, Y, and Z are each independently selected from a carbon atom or a nitrogen atom.

[0062] Existing boron-containing compounds have a large conjugated planar structure, which is prone to concentration quenching under electrical excitation, and there is a relatively serious efficiency roll-off problem in the device. The boron-containing compounds provided in the embodiments of the present application introduce large sterically hindered heterocyclic aromatic hydrocarbon fragments, which make the molecules present a certain degree of distorted structure, effectively suppressing the concentration quenching effect, and the introduction of heteroatoms such as oxygen and sulfur is conducive to enhancing the spin-orbit coupling effect of the molecules, so that the molecules have a short delayed life, which is beneficial to improving the efficiency roll-off problem of the device. The electroluminescent devices and display panels based on the boron-containing compounds have higher luminous efficiency and good device life.

[0063] The boron-containing compound provided in the embodiment of the present application is dissolved in toluene solution (10 -5 mol / L) in a steady-state fluorescence spectrum with a wavelength range of 430-580 nm and a half-peak width of the spectrum less than 35 nm; the transient luminescence in a solid-state film has delayed luminescence with a lifetime of 1 us-100 ms.

[0064] In some embodiments of the present application, is selected from substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted anthracenyl. When the above groups are substituted, the substituents of the above groups can form a ring with the above groups. The design can make the molecules of the boron-containing compound asymmetrically substituted, and under the condition of electrical excitation, it is easy to obtain a better horizontal dipole orientation, thereby enhancing the light extraction efficiency of the device.

[0065] Specifically, You can choose from any of the following structures:

[0066]

[0067] Among them, “*” indicates the connection site;

[0068] R 1 Each occurrence is independently selected from H, substituted or unsubstituted C6-C 40 aryl, or substituted or unsubstituted C5-C 40 heteroaryl;

[0069] In some embodiments, adjacent R 1 They may or may not form a ring.

[0070] In some embodiments of the present application, the general structural formula of the boron-containing compound is as shown in the following formula (I-1) or formula (I-2):

[0071]

[0072] Each independently selected from substituted or unsubstituted C6-C 30 aryl, or substituted or unsubstituted C6-C 30 of heteroaryl.

[0073] Optionally, Each is independently selected from a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted benzofuran group, a substituted or unsubstituted indole group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted carbazole group or a substituted or unsubstituted triphenylamine group.

[0074] 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.

[0075] Each occurrence of R is independently selected from a single bond, CR4R5, CO, SiR4R5, NR4, POR4, O, S, Se, -Te-, SO or SO2; R4 and R5 are each independently selected from H, C1-C 30 Alkyl or C5-C 30 of aromatic groups.

[0076] By alternating electron-deficient B elements with electron-rich N elements, and utilizing the opposing resonance effects of B and N atoms, multiple resonance thermally activated delayed fluorescence (MR-TADF) is constructed. The multiple resonance effect induces the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) to be located on different atoms, weakening the bonding / antibonding characteristics between atoms. This greatly reduces the change in electron density between atoms caused by the radiative transition from the lowest excited state to the ground state, thereby reducing stretching vibrations and effectively achieving narrow spectral emission (FWHM < 30nm). At the same time, the molecular thermally activated delayed fluorescence properties also ensure the high luminescence efficiency of the material.

[0077] The boron-containing compounds of the above formula (I-1) or (I-2) can easily obtain a better horizontal dipole orientation under electrical excitation conditions by designing asymmetrically substituted boron and nitrogen molecules, thereby enhancing the light extraction efficiency of the device. Moreover, under the premise of affecting the half-peak width of the spectrum, the introduction of large sterically hindered heterocyclic aromatic hydrocarbon fragments makes the molecules present a certain twisted structure, which helps to suppress the concentration quenching effect. Moreover, the introduction of heteroatoms such as oxygen and sulfur is conducive to enhancing the spin-orbit coupling effect of the molecules, so that the molecules have a shorter delayed life, which helps to alleviate the efficiency roll-off problem of the device.

[0078] Optionally, in some embodiments, Each is independently selected from a phenyl group which is substituted or unsubstituted by a deuterium atom, -CH3, -C(CH3)3, -CF3, -CN or -OCH3, a benzothiophene group, a biphenyl group, a naphthyl group, a quinazoline group, a carbazole group substituted by benzene or a dibenzofuran group.

[0079] Alternatively, in some embodiments, R1, R2, and R3 are each independently selected from a hydrogen atom, CN, CF3, or -OCH3.

[0080] Alternatively, in some embodiments, each occurrence of R is independently selected from a single bond, CR4R5, CO, SiR4R5, O, S, Se, -Te-, SO or SO2, and R4 and R5 are each independently selected from H, C1-C 10 Alkyl or C6-C 20 of aromatic groups.

[0081] Specifically, in some embodiments, the boron-containing compound is selected from at least one of the compounds represented by the following structural formulas:

[0082]

[0083]

[0084]

[0085] Based on the above boron-containing compound, an embodiment of the present application further provides an electroluminescent device comprising an anode, a cathode, and a light-emitting layer located between the anode and the cathode. The light-emitting layer comprises the boron-containing compound in the above embodiment.

[0086] The light-emitting layer includes a host light-emitting material, a sensitizer and a guest light-emitting material, and the boron compound can be used as the guest light-emitting material.

[0087] In some embodiments, the sensitizer may be at least one of a phosphorescent material and a thermally activated delayed fluorescent material. Furthermore, the sensitizer is preferably a material having an emission peak in the range of 440-600 nm, phosphorescent emission, and a phosphorescence lifetime in the range of 1 μs to 100 ms. The sensitizer has a HOMO energy level in the range of -6.0 eV to -5.0 eV, and a LUMO energy level in the range of -3.0 to -4.0 eV.

[0088] Furthermore, in some embodiments, the boron compound is selected from a compound represented by a structural formula having a luminescence spectrum peak at 480-580 nm, a spectral half-width less than 60 nm, a HOMO energy level range of -6.0 eV to -5.0 eV, and a LUMO energy level range of -3.0 to -4.0 eV.

[0089] In some embodiments, the electroluminescent device may further include a hole injection layer, a hole transport layer, and an electron blocking layer located between the anode and the light-emitting layer and sequentially stacked on the anode.

[0090] In some embodiments, the electroluminescent device further includes a hole blocking layer, an electron transport layer, and an electron injection layer located between the light-emitting layer and the cathode and sequentially stacked on the light-emitting layer.

[0091] The electroluminescent device described in the present application can be selected from, but not limited to, organic light emitting diodes (OLEDs), organic photovoltaic cells, organic light emitting cells, organic field effect transistors, organic light emitting field effect transistors, organic lasers, organic spintronic devices, organic sensors and organic plasmon emission diodes, etc., with OLED being particularly preferred.

[0092] In an embodiment of the present application, the anode may include 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.

[0093] 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 and used 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, electron beam (e-beam), and the like.

[0094] In some embodiments, the anode is patterned. Patterned ITO conductive substrates are commercially available and can be used to prepare the electroluminescent device according to the present application.

[0095] In the present invention, the cathode may comprise a conductive metal or metal oxide, and may easily inject electrons into the electron injection layer or the electron transport layer or directly into the light emitting layer.

[0096] In principle, any material that can be used as a cathode in an OLED is suitable for use as the cathode material in the device of this application. Examples of cathode materials include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloys, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, and ITO. The cathode material can be deposited using any suitable technique, such as physical vapor deposition (PVD), including radio frequency magnetron sputtering, vacuum thermal evaporation, and electron beam (e-beam).

[0097] The hole injection material, hole transport material, hole blocking material, electron blocking material, electron transport material and 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 commonly used as a hole injection material, hole transport material, electron blocking material, electron transport material and electron injection material.

[0098] The present application also relates to the application of the electroluminescent device according to the present application in various electronic devices, including but not limited to display devices, lighting devices, light sources, sensors, X-ray scintillator bio-imaging, etc. Examples of display devices include but are not limited to mobile phones, car displays, AR, VR, laptop computers, televisions, etc.

[0099] The present application also provides a display panel comprising the aforementioned electroluminescent device. The display panel may further comprise a pixel driving circuit for driving the electroluminescent device to emit light, the pixel driving circuit being electrically connected to the electroluminescent device. The pixel driving circuit includes, but is not limited to, a thin-film transistor driving circuit. Specific embodiments

[0101] The present invention will be described in detail below by way of specific examples, which are only some examples of the present invention and are not intended to limit the present invention. The raw materials used in the following examples, unless otherwise specified, are commercially available products. 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: cuprous 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-butylphosphine tetrafluoroborate; PA: pivalic acid; CH3MgBr: methylmagnesium bromide; Cs2CO3: cesium carbonate.

[0102] Example 1

[0103] The synthetic route of the target compound 1 of this embodiment is as follows:

[0104]

[0105] Synthesis steps:

[0106] 1.1 Synthesis of Intermediate 1-a: A 500 mL two-necked flask was charged with 1-bromo-2,6-dichlorobenzene (11.3 g, 50 mmol), 2,4-dibromocarbazole (19.5 g, 60 mmol), and anhydrous potassium carbonate (9.66 g, 70 mmol). The flask was evacuated three times under an argon atmosphere, and ultra-dry dimethyl sulfoxide (150 mL) was added. The mixture was then reacted at 150°C for 48 h. After the reaction mixture cooled to room temperature, it was extracted three times with dichloromethane (300 mL × 3). The excess solvent was removed by rotary evaporation, and then purified by column chromatography to obtain Intermediate 1-a (22.14 g, 85% yield).

[0107] 1.2 Synthesis of Intermediate 1-b: A 500 mL two-necked flask was charged with 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), and sodium tert-butoxide (8.06 g, 84 mmol). The mixture was purged three times under an argon atmosphere, and ultra-dry toluene (150 mL) was added. The mixture was then reacted at 110°C for 48 h. After cooling to room temperature, the reaction mixture was extracted three times with dichloromethane (DCM) (300 mL × 3). The excess solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to obtain Intermediate 1-b (22.6 g, 80% yield).

[0108] 1.3 Synthesis of Intermediate 1-c: To a 500 mL reaction flask, add Intermediate 1-b (22.6 g, 33 mmol) and 330 mL of m-xylene. n-Butyllithium in n-hexane (13.2 mL, 17.2 M, 33.66 mmol) was added dropwise at -78°C and stirred for one hour. The mixture was then heated and stirred at 60°C for 2 hours. The low-boiling solvent was then removed by distillation under reduced pressure. Boron tribromide (9.3 g, 37 mmol) was added dropwise at -78°C and stirred at room temperature for 1 hour. N,N-Diisopropylethylamine (4.9 g, 37 mmol) was then added dropwise at 0°C and stirred at 140°C for 24 hours. The mixture was cooled to room temperature, and aqueous sodium acetate was added and stirred. The organic layer was extracted with DCM, concentrated, and purified by column chromatography to afford Intermediate 1-c (9.6 g, 15 mmol, 50% yield).

[0109] 1.4 Synthesis of Intermediate 1-d: A 500 mL two-necked flask was charged with 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), and sodium tert-butoxide (2.88 g, 30 mmol). The mixture was purged three times under an argon atmosphere. Anhydrous toluene (150 mL) was added, and the mixture was reacted at 110°C for 36 h. After cooling to room temperature, the reaction mixture was extracted three times with dichloromethane (DCM) (200 mL × 3). Excess solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to obtain Intermediate 1-d (11.6 g, 80% yield).

[0110] 1.5 Synthesis of target compound 1: In a 500 mL two-necked flask, intermediate 1-d (11.6 g, 12 mmol), palladium acetate (269 mg, 1.2 mmol), and silver oxide (5.57 g, 24 mmol) were added. The mixture was evacuated three times under an argon atmosphere, and pivalic acid (120 mL) was added. After reacting at 150°C for 6 h, anhydrous potassium carbonate (552 mg, 4 mmol) was added and the reaction was continued for 12 h. After the reaction temperature was cooled to room temperature, saturated aqueous sodium bicarbonate solution was added and stirred. The organic layer was extracted with DCM, concentrated, and purified by column chromatography to obtain the product target compound 1 (5 g, 5.4 mmol, yield 45%).

[0111] Example 2

[0112] The synthetic route of target compound 2 in this example is as follows:

[0113]

[0114] Synthesis steps:

[0115] 2.1 Synthesis of intermediate 2-a: 10,15-dihydro-5H-diindolo[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) were added to a 250 mL two-necked flask. The mixture was evacuated three times under an argon atmosphere, anhydrous o-dichlorobenzene (150 mL) was added, and the mixture was reacted at 220 ° C. for 50 h. After the reaction was completed, the mixture was cooled to room temperature and extracted three times with DCM and water. The organic phases were combined and the solvent was removed. Intermediate 2-a (6 g, 9 mmol, yield 15%) was obtained by column chromatography.

[0116] 2.2 Synthesis of Intermediate 2-b: A 500 mL two-necked flask was charged with intermediate 2-a (6 g, 9 mmol). The mixture was evacuated three times under an argon atmosphere, and anhydrous tetrahydrofuran (200 mL) was added. The apparatus was then placed in a dry ice / acetone bath at -78°C and cooled for 15 min. A solution of n-butyllithium in n-hexane (45 mL, 18 mmol) was added dropwise to the reaction flask using a syringe and the reaction was continued at -78°C for another 1 h. Diphenylchlorosilane was then added, the reaction was continued at room temperature for 12 h, and then cooled to room temperature. The mixture was extracted three times with DCM and water. The organic phases were combined and the solvent was removed. Intermediate 2-b (5.4 g, 60% yield) was obtained by column chromatography.

[0117] 2.3 Synthesis of intermediate 2-c: In a 500 mL two-necked flask, intermediate 2-b (4.3 g, 5 mmol), 3,3-dimethyl-1-butene (3.2 mL, 25 mmol), and RhCl(PPh3)3 (46 mg, 0.05 mmol) were added. The mixture was evacuated three times under an argon atmosphere. Anhydrous 1,4-dioxane (100 mL) was added and the mixture was reacted at 135 ° C for 24 h. After the reaction was completed, the mixture was cooled to room temperature and extracted three times with DCM and water. The organic phases were combined and the solvent was removed. The intermediate 2-c (1.8 g, yield 84%) was obtained by column chromatography.

[0118] 2.4 Synthesis of Intermediate 2-d: A 500 mL two-necked flask was charged with 1-bromo-2,6-dichlorobenzene (452 mg, 2 mmol), phenothiazine (400 mg, 2 mmol), tris(dibenzylideneacetone)dipalladium (184 mg, 0.2 mmol), 2-dicyclohexylphosphine-2′,6′-dimethoxy-1,1′-biphenyl (82 mg, 0.2 mmol), and sodium tert-butoxide (240 mg, 2.5 mmol). The flask was purged three times under an argon atmosphere. Ultra-dry toluene (200 mL) was added, and the mixture was reacted at 110°C for 24 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and the product was purified by column chromatography to obtain Intermediate 2-d (577 mg, 75% yield).

[0119] 2.5 Synthesis of Intermediate 2-e: In a 100 mL two-necked flask, intermediate 2-d (385 mg, 1 mmol), intermediate 2-c (860 mg, 1 mmol), and anhydrous potassium carbonate (276 mg, 2 mmol) were added. The mixture was evacuated three times under an argon atmosphere, and ultra-dry dimethyl sulfoxide (10 mL) was added. The mixture was then reacted at 150°C for 24 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and then purified by column chromatography to obtain intermediate 2-e (800 mg, 76% yield).

[0120] 2.6 Synthesis of Compound 2: To a 100 mL two-necked flask, intermediate 2-e (600 mg, 0.5 mmol) and 10 mL of m-xylene were added dropwise. A solution of n-butyllithium in n-hexane (1 mol / L, 0.2 mL, 0.51 mmol) was added dropwise at -40°C and stirred for 1 h. Boron tribromide (190 mg, 0.75 mmol) was then added dropwise at -78°C. The mixture was stirred at room temperature for 1 h. N,N-diisopropylethylamine (100 mg, 0.75 mmol) was then added dropwise at 0°C. The mixture was heated and stirred 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 afford the product, Compound 2 (250 mg, 0.225 mmol, 45% yield).

[0121] Example 3

[0122] The synthetic route of target compound 3 in this example is as follows:

[0123]

[0124] Synthesis steps:

[0125] 3.1 Synthesis of Intermediate 3-a: A 1000 mL reaction flask was charged with 2,4-dibromocarbazole (13.0 g, 40 mmol), phenoxazine (6.41 g, 35 mmol), palladium acetate (420 mg, 1.75 mmol), tri-tert-butylphosphine tetrafluoroborate (1.0 g, 3.5 mmol), and sodium tert-butoxide (2.45 g, 42 mmol). The flask was evacuated three times under an argon atmosphere, and anhydrous toluene (400 mL) was added. The reaction mixture was then refluxed at 110°C for 36 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and then purified by column chromatography to obtain Intermediate 3-a (10.2 g, 24 mmol, 70% yield).

[0126] 3.2 Synthesis of Intermediate 3-b: In a 500 mL two-necked flask, intermediate 3-a (10.2 g, 24 mmol), phenothiazine (4.88 g, 24 mmol), palladium acetate (288 mg, 1.2 mmol), tri-tert-butylphosphine tetrafluoroborate (680 mg, 2.4 mmol), and sodium tert-butoxide (1.75 g, 30 mmol) were added. The mixture was evacuated three times under an argon atmosphere, and anhydrous toluene (250 mL) was added. The mixture was then refluxed at 110° C. for 36 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and then purified by column chromatography to obtain intermediate 3-b (9.8 g, 18 mmol, 75% yield).

[0127] 3.3 Synthesis of intermediate 3-c: In a 500 mL two-necked flask, intermediate 3-b (9.8 g, 18 mmol), palladium acetate (410.4 mg, 1.8 mmol), and silver oxide (4.17 g, 18 mmol) were added. The mixture was evacuated three times under an argon atmosphere, and pivalic acid (180 mL) was added. After reacting at 150°C for 6 h, anhydrous potassium carbonate (412 mg, 3 mmol) was added and the reaction was continued for 12 h. After the reaction temperature was cooled to room temperature, saturated aqueous sodium bicarbonate solution was added and stirred until the pH of the solution system was neutral. The organic layer was then extracted with DCM, concentrated, and purified by column chromatography to obtain intermediate 3-c (4.87 g, 9 mmol, yield 50%).

[0128] 3.4 Synthesis of Intermediate 3-d: A 250 mL two-necked flask was charged with 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), and sodium tert-butoxide (1.92 g, 20 mmol). The flask was purged three times under an argon atmosphere. Ultra-dry toluene (100 mL) was added, and the mixture was reacted at 110°C for 48 h. After cooling to room temperature, the reaction mixture was extracted three times with dichloromethane (DCM) (200 mL × 3). Excess solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to obtain Intermediate 3-d (3.8 g, 9.6 mmol, 80% yield).

[0129] 3.5 Synthesis of Intermediate 3-e: A 250 mL two-necked flask was charged with Intermediate 3-d (3.8 g, 9 mmol), Intermediate 3-c (4.87 g, 9 mmol), and anhydrous potassium carbonate (2.07 g, 15 mmol). The mixture was evacuated three times under an argon atmosphere, and ultra-dry dimethyl sulfoxide (90 mL) was added. The mixture was then reacted at 150°C for 48 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and intermediate 3-e (6.3 g, 7 mmol, 80% yield) was obtained by column chromatography.

[0130] 3.6 Synthesis of Target Compound 3: To a 250 mL reaction flask, add intermediate 3-e (6.3 g, 7 mmol) and 140 mL of p-xylene. Add n-butyllithium in n-hexane (2.8 mL, 3.65 M, 7.14 mmol) dropwise at -40°C and stir for 1 h. Next, add boron tribromide (2.5 g, 10 mmol) dropwise at -78°C, stir at room temperature for 1 h, then add N,N-diisopropylethylamine (1.27 g, 10 mmol) dropwise at 0°C. Heat and stir at 150°C for 24 h. Cool to room temperature, extract the organic layer with DCM, concentrate, and purify by column chromatography to yield target compound 3 (2.33 g, 2.8 mmol, 40% yield).

[0131] Example 4

[0132] The synthetic route of target compound 4 of this embodiment is as follows:

[0133]

[0134] Synthesis steps:

[0135] 4.1 Synthesis of Intermediate 4-a: Under argon atmosphere, tripolyindole (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 into a 100 mL two-necked flask, 50 mL of o-dichlorobenzene and 3.2 mL of methyl o-iodobenzoate (20 mmol) were added, the temperature was raised to 220°C, and the mixture was stirred under argon for 50 h. The mixture was then cooled to room temperature, extracted with DCM and water, the organic phase was separated, and dried over anhydrous sodium sulfate. The organic phase was filtered to remove the solvent and purified by column chromatography to obtain Intermediate 4-a (1.4 g, yield: 23%).

[0136] 4.2 Synthesis of intermediate 4-b: Under argon atmosphere, intermediate 4-a (1.2 g, 2 mmol) was added to a 100 mL two-necked flask, and 18 mL of anhydrous tetrahydrofuran was added and stirred. Then 20 mL (20 mmol) of methylmagnesium bromide was added dropwise. The mixture was reacted at 80°C for 12 h and then cooled to room temperature. Ethyl acetate and water were added for extraction, the organic phase was separated, and anhydrous sodium sulfate was added for drying. The organic phase obtained by filtration was free of solvent and purified by column chromatography to obtain intermediate 4-b (0.37 g, 0.6 mmol, yield: 30%).

[0137] 4.3 Synthesis of Intermediate 4-c: Under argon atmosphere, intermediate 4-b (0.61 g, 1 mmol) was weighed into a 100 mL single-necked flask, 20 mL of glacial acetic acid was added, and then 3 mL of concentrated hydrochloric acid was added. The mixture was heated to 130°C and reacted for 4 h. The mixture was then cooled to room temperature and extracted with dichloromethane and water. The organic phase was separated and dried over anhydrous sodium sulfate. The organic phase was filtered to remove the solvent and purified by column chromatography to obtain intermediate 4-c (0.35 g, 60% yield).

[0138] 4.4 Synthesis of Intermediate 4-d: A 100 mL two-necked flask was charged with 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), and sodium tert-butoxide (240 mg, 2.5 mmol). The mixture was purged three times under an argon atmosphere. Ultra-dry toluene (20 mL) was added, and the mixture was reacted at 110°C for 24 h. After cooling to room temperature, the reaction mixture was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to obtain Intermediate 4-d (652 mg, 1.5 mmol, 75% yield).

[0139] 4.5 Synthesis of Intermediate 4-e: In a 100 mL two-necked flask, intermediate 4-d (440 mg, 1 mmol), intermediate 4-c (575 mg, 1 mmol), and anhydrous potassium carbonate (280 mg, 2 mmol) were added. The mixture was evacuated three times under an argon atmosphere, and ultra-dry dimethyl sulfoxide (20 mL) was added. The mixture was then reacted at 150°C for 24 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and the intermediate was purified by column chromatography to obtain the intermediate (750 mg, 0.75 mmol, 75% yield).

[0140] 4.6 Synthesis of Target Compound 4: Intermediate 4-e (500 mg, 0.5 mmol) and 10 mL of m-xylene were added to a 100 mL double-bottle flask. A solution of n-butyllithium in n-hexane (0.2 mL, 1 M, 0.51 mmol) was added dropwise at -40°C and stirred for 1 h. Boron tribromide (188 mg, 0.75 mmol) was then added dropwise at -78°C. The mixture was stirred at room temperature for 1 h. N,N-diisopropylethylamine (100 mg, 0.75 mmol) was then added dropwise at 0°C. The mixture was heated and stirred 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 yield target compound 4 (202 mg, 0.2 mmol, 40% yield).

[0141] Example 5

[0142] The synthetic route of target compound 5 of this embodiment is as follows:

[0143]

[0144] Synthesis steps:

[0145] 5.1 Synthesis of intermediate 5-a: Under argon atmosphere, tripolyindole (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) were weighed in a 100 mL two-necked flask, 50 mL of o-dichlorobenzene was added, the temperature was raised to 220°C and the reaction was carried out for 50 h, then cooled to room temperature, extracted with dichloromethane and water, the organic phase was separated, dried over anhydrous sodium sulfate, the solvent was removed by rotary evaporator, and intermediate 5-a (1.5 g, 2 mmol, yield: 20%) was obtained by column chromatography.

[0146] 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 (volume ratio 8:1) was added and stirred for 30 min. The stirred mixture was cooled to room temperature, and the organic layer was extracted with DCM, concentrated, and purified by column chromatography to obtain Intermediate 5-b (0.23 g, yield: 35%).

[0147] 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), and potassium carbonate (2.76 g, 20 mmol). The mixture was evacuated three times under an argon atmosphere, and ultra-dry dimethyl sulfoxide (20 mL) was added. The mixture was then reacted at 150°C for 24 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and intermediate 5-c (3.5 g, 7.5 mmol, 75% yield) was obtained.

[0148] 5.4 Synthesis of Intermediate 5-d: To a 250 mL two-necked flask were added Intermediate 5-c (470 mg, 1 mmol), Intermediate 5-b (525 mg, 1 mmol), and anhydrous potassium carbonate (414 mg, 3 mmol). The mixture was evacuated three times under an argon atmosphere, and ultra-dry dimethyl sulfoxide (20 mL) was added. The mixture was then reacted at 150°C for 24 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to obtain Intermediate 5-d (673 mg, 70% yield).

[0149] 5.5 Synthesis of Target Compound 5: To a 100 mL two-necked flask were added intermediate 5-d (480 mg, 0.5 mmol) and 10 mL of m-xylene. A solution of n-butyllithium in n-hexane (0.2 mL, 1 M, 0.51 mmol) was added dropwise at -40°C and stirred for 1 h. Boron tribromide (188 mg, 0.75 mmol) was then added dropwise at -78°C. The mixture was stirred at room temperature for 1 h. N,N-diisopropylethylamine (100 mg, 0.75 mmol) was then added dropwise at 0°C. The mixture was heated and stirred 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 yield target compound 5 (204 mg, 0.23 mmol, 46% yield).

[0150] Example 6

[0151] The synthetic route of target compound 6 in this example is as follows:

[0152]

[0153] Synthesis steps:

[0154] 6.1 Synthesis of Intermediate 6-a: A 1000 mL reaction flask was charged with 2,3-dibromocarbazole (19.5 g, 60 mmol), 3,6-di-tert-butylcarbazole (16.74 g, 60 mmol), and cesium carbonate (21.2 g, 65 mmol). The mixture was purged three times under an argon atmosphere. N,N-dimethylformamide (700 mL) was added and the reaction was incubated at 110°C for 36 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and intermediate 6-a (23.5 g, 45 mmol, 75% yield) was obtained.

[0155] 6.2 Synthesis of Intermediate 6-b: To a 1000 mL reaction flask were added Intermediate 6-a (23.5 g, 45 mmol), phenoxazine (9.15 g, 50 mmol), palladium acetate (600 mg, 2.5 mmol), tri-tert-butylphosphine tetrafluoroborate (1.41 g, 5 mmol), and sodium tert-butoxide (5.76 g, 60 mmol). The mixture was purged three times under an argon atmosphere, and anhydrous toluene (200 mL) was added. The reaction was then incubated at 110°C for 36 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to obtain Intermediate 6-b (22 g, 80% yield).

[0156] 6.3 Synthesis of intermediate 6-c: In a 500 mL two-necked flask, intermediate 6-b (22 g, 36 mmol), palladium acetate (807 mg, 3.6 mmol), and silver oxide (16.71 g, 72 mmol) were added. The mixture was evacuated three times under an argon atmosphere, and pivalic acid (360 mL) was added. After reacting at 150°C for 6 h, anhydrous potassium carbonate (1.65 g, 12 mmol) was added and the reaction was continued for 12 h. After the reaction temperature was cooled to room temperature, saturated aqueous sodium bicarbonate solution was added and stirred. The organic layer was extracted with DCM, concentrated, and purified by column chromatography to obtain intermediate 6-c (11.2 g, 18 mmol, 50% yield).

[0157] 6.4 Synthesis of Intermediate 6-d: A 500 mL two-necked flask was charged with 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-dicyclohexylphosphine-2′,6′-dimethoxy-1,1′-biphenyl (1.23 g, 3 mmol), and sodium tert-butoxide (3.6 g, 37.5 mmol). The flask was purged three times under an argon atmosphere. Ultra-dry toluene (300 mL) was added, and the mixture was reacted at 110°C for 24 h. After cooling to room temperature, the reaction mixture was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and the product was purified by column chromatography to afford Intermediate 6-d (8.4 g, 75% yield).

[0158] 6.5 Synthesis of Intermediate 6-e: To a 500 mL two-necked flask were added Intermediate 6-d (8.4 g, 18 mmol), Intermediate 6-c (11.2 g, 18 mmol), and anhydrous potassium carbonate (2.76 g, 20 mmol). The mixture was evacuated three times under an argon atmosphere, and ultra-dry dimethyl sulfoxide (150 mL) was added. The mixture was then reacted at 150°C for 48 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and intermediate 6-e (22.14 g, 80% yield) was obtained.

[0159] 6.6 Synthesis of Target Compound 6: To a 500 mL reaction flask, add intermediate 6-e (22.1 g, 14 mmol) and 280 mL of p-xylene. Add n-butyllithium in n-hexane (5.6 mL, 7.3 mol / L, 14.28 mmol) dropwise at -40°C and stir for 1 h. Next, add boron tribromide (5 g, 20 mmol) dropwise at -78°C and stir at room temperature for 1 h. Then, add N,N-diisopropylethylamine (2.58 g, 20 mmol) dropwise at 0°C and heat with stirring at 150°C for 24 h. Cool to room temperature, extract the organic layer with DCM, concentrate, and purify by column chromatography to yield target compound 6 (6.4 g, 7.1 mmol, 45% yield).

[0160] Example 7

[0161] The synthetic route of target compound 7 in this example is as follows:

[0162]

[0163] Synthesis steps:

[0164] 7.1 Synthesis of Intermediate 7-a: To a 1000 mL reaction flask, add 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-butylphosphine tetrafluoroborate (1.69 g, 6 mmol), and sodium tert-butoxide (6.72 g, 70 mmol). Under an argon atmosphere, evacuate the flask three times, add anhydrous toluene (400 mL), and react at 110°C for 48 h. After cooling to room temperature, extract the mixture three times with DCM. Remove excess solvent using a rotary evaporator, and purify the mixture by column chromatography to obtain Intermediate 7-a (17.4 g, 21 mmol, 70% yield).

[0165] 7.2 Synthesis of intermediate 7-b: In a 500 mL two-necked flask, intermediate 7-a (17.4 g, 21 mmol), palladium acetate (471 mg, 2.1 mmol), and silver oxide (9.75 g, 42 mmol) were added. The mixture was evacuated three times under an argon atmosphere, and pivalic acid (210 mL) was added. After reacting at 150°C for 6 h, anhydrous potassium carbonate (973 mg, 7 mmol) was added and the reaction was continued for 12 h. After the reaction temperature was cooled to room temperature, saturated aqueous sodium bicarbonate solution was added and stirred. The organic layer was extracted with DCM, concentrated, and purified by column chromatography to obtain intermediate 7-b (8.25 g, 10 mmol, yield 48%).

[0166] 7.3 Synthesis of Intermediate 7-c: A 500 mL two-necked flask was charged with 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-dicyclohexylphosphine-2′,6′-dimethoxy-1,1′-biphenyl (410 mg, 1 mmol), and sodium tert-butoxide (2.4 g, 25 mmol). Under an argon atmosphere, the mixture was purged three times. Ultra-dry toluene (300 mL) was added, and the mixture was refluxed at 110°C for 24 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and the product was purified by column chromatography to obtain Intermediate 7-c (8.33 g, 16 mmol, 80% yield).

[0167] 7.4 Synthesis of Intermediate 7-d: To a 500 mL two-necked flask were added Intermediate 7-c (5.21 g, 10 mmol), Intermediate 7-b (8.25 g, 10 mmol), and anhydrous potassium carbonate (2.1 g, 15 mmol). The mixture was evacuated three times under an argon atmosphere, and ultra-dry dimethyl sulfoxide (100 mL) was added. The mixture was then reacted at 150°C for 36 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to obtain Intermediate 7-d (9.17 g, 7 mmol, 70% yield).

[0168] 7.5 Synthesis of Target Compound 7: To a 500 mL two-necked flask, intermediate 7-d (9.17 g, 7 mmol) and 140 mL of p-xylene were added dropwise. A solution of n-butyllithium in n-hexane (2.8 mL, 3.6 M, 7.14 mmol) was added dropwise at -40°C and stirred for 1 h. Boron tribromide (2.5 g, 10 mmol) was then added dropwise at -78°C. The mixture was stirred at room temperature for 1 h. N,N-diisopropylethylamine (1.27 g, 10 mmol) was then added dropwise at 0°C. The mixture was heated and stirred 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 yield target compound 7 (3.7 g, 3 mmol, 43% yield).

[0169] Example 8

[0170] The synthetic route of target compound 8 in this example is as follows:

[0171]

[0172] Synthesis steps:

[0173] 8.1 Synthesis of Intermediate 8-a: A 1000 mL two-necked flask was charged with 4-bromo-3,5-dichlorobenzonitrile (12.5 g, 50 mmol), 2,4-dibromocarbazole (19.5 g, 60 mmol), and anhydrous potassium carbonate (9.66 g, 70 mmol). The mixture was evacuated three times under an argon atmosphere, and ultra-dry dimethyl sulfoxide (150 mL) was added. The mixture was then reacted at 150°C for 48 h. After cooling to room temperature, the reaction mixture was extracted three times with dichloromethane (DCM) (300 mL × 3). Excess solvent was removed by rotary evaporation, and intermediate 8-a (20.36 g, 76% yield) was obtained by column chromatography.

[0174] 8.2 Synthesis of Intermediate 8-b: To a 1000 mL two-necked flask was added 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), and sodium tert-butoxide (3.84 g, 40 mmol). The flask was purged three times under an argon atmosphere. Ultra-dry toluene (300 mL) was added, and the mixture was reacted at 110°C for 48 h. After cooling to room temperature, the reaction mixture was extracted three times with dichloromethane (DCM) (300 mL × 3). Excess solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to afford Intermediate 8-b (14 g, 70% yield).

[0175] 8.3 Synthesis of Intermediate 8-c: To a 500 mL reaction flask, add Intermediate 8-b (13.4 g, 20 mmol) and 200 mL of m-xylene. Add n-butyllithium in n-hexane (8.2 mL, 2.5 M, 20.4 mmol) dropwise at -78°C and stir for 1 h. Heat and stir at 60°C for 2 h, then remove the low-boiling solvent by distillation under reduced pressure. Add boron tribromide (5.64 g, 22.4 mmol) dropwise at -78°C and stir at room temperature for 1 h. Add N,N-diisopropylethylamine (2.96 g, 22.4 mmol) dropwise at 0°C and stir at 140°C for 24 h. Cool to room temperature, add aqueous sodium acetate solution and stir. Extract the organic layer with DCM, concentrate, and purify by column chromatography to afford Intermediate 8-c (4.9 g, 8.2 mmol, 40% yield).

[0176] 8.4 Synthesis of Intermediate 8-d: A 500 mL two-necked flask was charged with 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), and sodium tert-butoxide (960 mg, 10 mmol). The mixture was purged three times under an argon atmosphere. Anhydrous toluene (50 mL) was added, and the mixture was reacted at 110°C for 36 h. After the reaction mixture cooled to room temperature, it was extracted three times with dichloromethane (100 mL × 3). The excess solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to obtain Intermediate 8-d (3 g, 70% yield).

[0177] 8.5 Synthesis of target compound 8: Into a 200 mL two-necked flask were added intermediate 8-d (4.36 g, 5 mmol), palladium acetate (112 mg, 0.5 mmol), and silver oxide (2.31 g, 10 mmol). The mixture was evacuated three times under an argon atmosphere, and pivalic acid (50 mL) was added. After reacting 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 temperature was cooled to room temperature, saturated aqueous sodium bicarbonate solution was added and stirred. The organic layer was extracted with DCM, concentrated, and purified by column chromatography to obtain the target compound 8 (1.8 g, 2.1 mmol, 42% yield).

[0178] Example 9

[0179] The synthetic route of target compound 9 in this example is as follows:

[0180]

[0181] Synthesis steps:

[0182] 9.1 Synthesis of Intermediate 9-a: A 1000 mL reaction flask was charged with 2,3-dibromocarbazole (19.5 g, 60 mmol), 3,6-di-tert-butylcarbazole (16.74 g, 60 mmol), and cesium carbonate (21.2 g, 65 mmol). The mixture was purged three times under an argon atmosphere. N,N-dimethylformamide (700 mL) was added and the reaction was incubated at 110°C for 36 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and intermediate 9-a (23.5 g, 75% yield) was obtained by column chromatography.

[0183] 9.2 Synthesis of Intermediate 9-b: To a 1000 mL reaction flask were added 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), and sodium tert-butoxide (5.76 g, 60 mmol). The reaction was purged three times under an argon atmosphere, and anhydrous toluene (400 mL) was added. The mixture was then reacted at 110°C for 36 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to obtain Intermediate 9-b (23.7 g, 68% yield).

[0184] 9.3 Synthesis of intermediate 9-c: In a 500 mL two-necked flask, intermediate 9-b (23.2 g, 30 mmol), palladium acetate (672 mg, 3 mmol), and silver oxide (13.9 g, 60 mmol) were added. The mixture was evacuated three times under an argon atmosphere, and pivalic acid (360 mL) was added. After reacting at 150°C for 6 h, anhydrous potassium carbonate (1.38 g, 10 mmol) was added and the reaction was continued for 12 h. After the reaction temperature was cooled to room temperature, saturated aqueous sodium bicarbonate solution was added and stirred. The organic layer was extracted with DCM, concentrated, and purified by column chromatography to obtain intermediate 9-c (9.9 g, 12.9 mmol, yield 43%).

[0185] 9.4 Synthesis of Intermediate 9-d: A 500 mL two-necked flask was charged with 4-bromo-3,5-dichlorobenzotrifluoride (5.88 g, 20 mmol), benzo[b][1,8]naphthyridine (4.63 g, 22 mmol), tris(dibenzylideneacetone)dipalladium (1.83 g, 2 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl (821 mg, 2 mmol), and sodium tert-butoxide (2.4 g, 25 mmol). The mixture was purged three times under an argon atmosphere. Ultra-dry toluene (200 mL) was added, and the mixture was reacted at 110°C for 24 h. After cooling to room temperature, the reaction mixture was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to afford Intermediate 9-d (6.05 g, 65% yield).

[0186] 9.4 Synthesis of Intermediate 9-e: To a 500 mL two-necked flask were added Intermediate 9-d (5.59 g, 12 mmol), Intermediate 9-c (9.2 g, 18 mmol), and anhydrous potassium carbonate (2.8 g, 20 mmol). The mixture was evacuated three times under an argon atmosphere, and ultra-dry dimethyl sulfoxide (150 mL) was added. The mixture was then reacted at 150°C for 48 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to obtain Intermediate 9-e (10.8 g, 9 mmol, 75% yield).

[0187] 9.4 Synthesis of Target Compound 9: To a 500 mL reaction flask, add intermediate 9-e (10.8 g, 9 mol) and 90 mL of p-xylene. Add n-butyllithium in n-hexane (3.7 mL, 9.18 mmol) dropwise at -40°C and stir for 1 h. Next, add boron tribromide (2.7 g, 10.8 mmol) dropwise at -78°C, stir at room temperature for 1 h, then add N,N-diisopropylethylamine (1.39 g, 10.8 mmol) dropwise at 0°C. Heat and stir at 150°C for 24 h. Cool to room temperature, extract the organic layer with DCM, concentrate, and purify by column chromatography to yield target compound 9 (3.9 g, 3.5 mmol, 38% yield).

[0188] Example 10

[0189] The synthetic route of the target compound 10 of this embodiment is as follows:

[0190]

[0191] Synthesis steps:

[0192] 10.1 Synthesis of Intermediate 10-a: To a 1000 mL reaction flask, add 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-butylphosphine tetrafluoroborate (845 mg, 3 mmol), and sodium tert-butoxide (3.84 g, 40 mmol). Under an argon atmosphere, evacuate the flask three times, add anhydrous toluene (400 mL), and react at 110°C for 48 h. After cooling to room temperature, the reaction mixture was extracted three times with DCM. Excess solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to obtain Intermediate 10-a (11.9 g, 20.5 mmol, 68% yield).

[0193] 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-azaindole[1,2-b]anthracene (6.59 g, 22 mmol), palladium acetate (225 mg, 1 mmol), tri-tert-butylphosphine tetrafluoroborate (564 mg, 2 mmol), and sodium tert-butoxide (2.30 g, 24 mmol). The flask was purged three times under an argon atmosphere. Anhydrous toluene (200 mL) was added, and the reaction was continued at 110°C for 36 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and the mixture was purified by column chromatography to obtain Intermediate 10-b (10.3 g, 13 mmol, 65% yield).

[0194] 10.3 Synthesis of intermediate 10-c: In a 500 mL two-necked flask, intermediate 10-b (8 g, 10 mmol), palladium acetate (225 mg, 1 mmol), and silver oxide (4.64 g, 20 mmol) were added. The mixture was evacuated three times under an argon atmosphere, and pivalic acid (100 mL) was added. After reacting at 150°C for 6 h, anhydrous potassium carbonate (690 mg, 5 mmol) was added and the reaction was continued for 12 h. After the reaction temperature was cooled to room temperature, saturated aqueous sodium bicarbonate solution was added and stirred. The organic layer was extracted with DCM, concentrated, and purified by column chromatography to obtain intermediate 10-c (3.72 g, 4.7 mmol, yield 47%).

[0195] 10.4 Synthesis of Intermediate 10-d: A 500 mL two-necked flask was charged with 4-bromo-3,5-dichlorobenzotrifluoride (2.94 g, 10 mmol), 4-methyl-10-hydrophenoxazine (1.35 g, 12 mmol), tris(dibenzylideneacetone)dipalladium (915 mg, 1 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxy-1,1'-biphenyl (410 mg, 1 mmol), and sodium tert-butoxide (1.34 g, 14 mmol). The flask was purged three times under an argon atmosphere. Ultra-dry toluene (100 mL) was added, and the mixture was reacted at 110°C for 24 h. After cooling to room temperature, the reaction mixture was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and the product was purified by column chromatography to afford Intermediate 10-d (2.69 g, 7 mmol, 70% yield).

[0196] 10.5 Synthesis of Intermediate 10-e: To a 500 mL two-necked flask were added Intermediate 10-d (1.92 g, 5 mmol), Intermediate 10-c (4 g, 5 mmol), and anhydrous potassium carbonate (828 mg, 6 mmol). The mixture was evacuated three times under an argon atmosphere, and ultra-dry dimethyl sulfoxide (50 mL) was added. The mixture was then reacted at 150°C for 48 h. After the reaction mixture cooled to room temperature, it was extracted three times with DCM. The excess solvent was removed by rotary evaporation, and intermediate 10-e (4.16 g, 3.65 mmol, 73% yield) was obtained.

[0197] 10.6 Synthesis of Target Compound 10: To a 500 mL reaction flask, add intermediate 10-e (10.8 g, 3 mol) and 30 mL of p-xylene. Add n-butyllithium in n-hexane (1.22 mL, 3.06 mmol) dropwise at -40°C and stir for 1 h. Next, add boron tribromide (0.9 g, 3.6 mmol) dropwise at -78°C, stir at room temperature for 1 h, then add N,N-diisopropylethylamine (465 mg, 3.6 mmol) dropwise at 0°C. Heat and stir at 150°C for 24 h. Cool to room temperature, extract the organic layer with DCM, concentrate, and purify by column chromatography to yield target compound 10 (1.08 g, 1 mmol, 35% yield).

[0198] The mass spectrometry (MS) and elemental analysis (EA) results of the target compounds synthesized in Examples 1-10 and Compound A (structural formula is referenced below) are shown in Table 1 below.

[0199] Table 1

[0200]

[0201]

[0202] The performance of the electroluminescent device comprising the above compounds is tested by using specific device examples 1-20 and comparative examples 1-2. Figure 1 As shown, 1—glass and conductive glass (ITO anode) substrate layer; 2—hole injection layer (HATCN, 10nm); 3—hole transport layer (TAPC, 30nm); 4—electron blocking layer (TCTA, 15nm); 5—light-emitting layer (20nm); 6—hole blocking layer (DBFPO, 20nm); 7—electron transport layer (ANT-BIZ, 30nm); 8—electron injection layer (LiQ, 1nm); 9—cathode (Al, 100nm).

[0203]

[0204] Among them, device embodiments 1-20 and device comparative example 1 are identical in device structure and manufacturing method except that the materials of the light-emitting layers are different.

[0205] The light-emitting layer of the device comparative example 1: compound A and the main light-emitting material mCBP, the evaporation ratio is 4:196.

[0206] The light-emitting layer of the device comparative example 2: compound A, photosensitizer Ir(ppy)3 and main light-emitting material mCBP, the evaporation ratio is 2:20:178.

[0207] The light-emitting layer of device example 1 is different from device comparative example 1 in that compound A is replaced by compound 1 synthesized in example 1.

[0208] The light-emitting layer of device example 2 is different from device comparative example 1 in that compound A is replaced by compound 2 synthesized in example 2.

[0209] The light-emitting layer of device example 3 is different from device comparative example 1 in that compound A is replaced by compound 3 synthesized in example 3.

[0210] The light-emitting layer of device example 4 is different from device comparative example 1 in that compound A is replaced by compound 4 synthesized in example 4.

[0211] The light-emitting layer of device example 5 is different from device comparative example 1 in that compound A is replaced by compound 5 synthesized in example 5.

[0212] The light-emitting layer of device example 6 is different from device comparative example 1 in that compound A is replaced by compound 6 synthesized in example 6.

[0213] The light-emitting layer of device example 7 is different from device comparative example 1 in that compound A is replaced by compound 7 synthesized in example 7.

[0214] The light-emitting layer of device example 8 is different from device comparative example 1 in that compound A is replaced by compound 8 synthesized in example 8.

[0215] The light-emitting layer of device example 9 is different from device comparative example 1 in that compound A is replaced by compound 9 synthesized in example 9.

[0216] The light-emitting layer of device example 10 is different from device comparative example 1 in that compound A is replaced by compound 10 synthesized in example 10.

[0217] The light-emitting layer of device example 11 is different from device comparative example 2 in that compound A is replaced by compound 1 synthesized in example 1.

[0218] The light-emitting layer of device example 12 is different from device comparative example 2 in that compound A is replaced by compound 2 synthesized in example 2.

[0219] The light-emitting layer of device example 13 is different from device comparative example 2 in that compound A is replaced by compound 3 synthesized in example 3.

[0220] The light-emitting layer of device example 14 is different from device comparative example 2 in that compound A is replaced by compound 4 synthesized in example 4.

[0221] The light-emitting layer of device example 15 is different from device comparative example 2 in that compound A is replaced by compound 5 synthesized in example 5.

[0222] The light-emitting layer of device example 16 is different from device comparative example 2 in that compound A is replaced by compound 6 synthesized in example 6.

[0223] The light-emitting layer of device example 17 is different from device comparative example 2 in that compound A is replaced by compound 7 synthesized in example 7.

[0224] The light-emitting layer of device example 18 is different from device comparative example 2 in that compound A is replaced by compound 8 synthesized in example 8.

[0225] The light-emitting layer of device example 19 is different from device comparative example 1 in that compound A is replaced by compound 9 synthesized in example 9.

[0226] The light-emitting layer of device example 20 is different from device comparative example 2 in that compound A is replaced by compound 10 synthesized in example 10.

[0227] The electroluminescent device can be made according to methods known in the art, for example, according to the method disclosed in the reference (Adv. Mater. 2003, 15, 277). The specific method is: under high vacuum conditions, the hole injection layer, hole transport layer, electron blocking layer, light emitting layer, hole blocking layer, electron transport layer, electron injection layer and cathode are sequentially deposited on a cleaned conductive glass (ITO) substrate. Figure 1 The device shown. At a current density of 10 mA / cm 2 The luminescence characteristics of the prepared device were recorded under the following conditions, as shown in Table 2. Wherein, Voltage is the operating voltage of the device, and CE is the current efficiency. The higher the current efficiency, the higher the carrier utilization rate of the device and the higher the luminescence efficiency.

[0228] Table 2

[0229]

[0230]

[0231] As can be seen from Table 2, compared to the electroluminescent device prepared in Comparative Example 1, the electroluminescent devices prepared in Device Examples 1-10 provided in the Examples of the present application have lower operating voltages, higher luminous efficiencies, and longer service lives. This may be because the compounds provided in the Examples of the present application, by introducing a heterocyclic aromatic hydrocarbon fragment with greater steric hindrance, cause the molecule to exhibit a certain degree of distorted structure, which can effectively suppress 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, thereby giving the molecule a short delayed life, thereby improving the luminous efficiency and service life of the device as a whole.

[0232] Compared with the electroluminescent devices prepared by device embodiments 1-10, the electroluminescent devices prepared by device embodiments 11-20 can further reduce the operating voltage, increase the luminescence and extend the service life. The possible reason is that by introducing phosphorescent materials into the light-emitting layer and combining them with the compounds provided in the embodiments of the present application, the efficient phosphorescent materials can capture triplet excitons in the electroluminescent device and transfer energy to the fluorescent molecules (compounds provided in the present application) through energy transfer, so that the fluorescent molecules emit light. While maintaining the narrow spectrum of the fluorescent molecules, efficient utilization of triplet excitons is achieved, thereby realizing an electroluminescent device with high efficiency, high color purity and high stability.

[0233] In the above embodiments, the description of each embodiment has its own focus. For parts that are not described in detail in a certain embodiment, reference can be made to the relevant descriptions of other embodiments.

[0234] The above is a detailed description of a compound, a mixture, and an electroluminescent device provided in the embodiments of the present application. The above description is only used to help understand the technical solution and its core idea of the present application; ordinary technicians in this field can modify the technical solutions described in the aforementioned embodiments or replace some of the technical features therein with equivalents, without causing the essence of the corresponding technical solutions to deviate from the scope of the technical solutions of the embodiments of the present application.

Claims

1. A boron-containing compound, characterized in that: The general structural formula of the boron-containing compound is shown in Formula (I-1) or Formula (I-2): to Each independently selected from substituted or unsubstituted C6-C 30 aryl, or substituted or unsubstituted C6-C 30 wherein the substituent is selected from deuterium, tritium, cyano, an alkyl group containing 1 to 20 carbon atoms, a heterocyclic group containing 3 to 20 ring atoms, an aromatic group containing 6 to 20 ring atoms, a heteroaromatic group containing 5 to 20 ring atoms, or a trifluoromethyl group; 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, at each occurrence, is independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -NR4-, -POR4-, -O-, -S-, -Se-, -Te-, -SO- or -SO2-; R4 and R5 are each independently selected from H, C1-C 30 Alkyl or C6-C 30 of aromatic groups.

2. The boron-containing compound according to claim 1, characterized in that The general structural formula of the compound is shown in Formula (I-1-1) or Formula (I-2-1): to Each independently selected from substituted or unsubstituted C6-C 30 aryl, or substituted or unsubstituted C5-C 30 wherein the substituent is selected from deuterium, tritium, cyano, an alkyl group containing 1 to 20 carbon atoms, a heterocyclic group containing 3 to 20 ring atoms, an aromatic group containing 6 to 20 ring atoms, a heteroaromatic group containing 5 to 20 ring atoms, or a trifluoromethyl group; 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 groups; Each occurrence of R is independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -NR4-, -POR4-, -O-, -S-, -Se-, -Te-, -SO- or -SO2-; R4 and R5 are each independently selected from H, C1-C 30 Alkyl or C6-C 30 of aromatic groups.

3. The boron-containing compound according to claim 2, characterized in that to Each is independently selected from substituted or unsubstituted phenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzothiophenyl, 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 quinazolinyl, and the substituent is selected from deuterium, tritium, cyano, an alkyl group containing 1 to 20 carbon atoms, a heterocyclic group containing 3 to 20 ring atoms, an aromatic group containing 6 to 20 ring atoms, a heteroaromatic group containing 5 to 20 ring atoms, or a trifluoromethyl group.

4. The boron-containing compound according to claim 2, characterized in that R1, R2, and R3 are each independently selected from a hydrogen atom, -CN, -CF3, or -OCH3.

5. The boron-containing compound according to claim 2, characterized in that Each occurrence of R is independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -O-, -S-, -Se-, -Te-, -SO- or -SO2-, and R4 and R5 are each independently selected from H, C1-C 10 Alkyl or C6-C 20 of aromatic groups.

6. A boron-containing compound, characterized in that: The general structural formula of the boron-containing compound is shown in Formula (I-1-1) or Formula (I-2-1): to Each is independently selected from a phenyl group which is substituted or unsubstituted by a deuterium atom, -CH3, -C(CH3)3, -CF3, -CN or -OCH3, a benzothiophene group, a biphenyl group, a naphthyl group, a quinazoline group, a carbazole group substituted by a phenyl group, or a dibenzofuran group; 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; Each occurrence of R is independently selected from a single bond, -CR4R5-, -CO-, -SiR4R5-, -NR4-, -POR4-, -O-, -S-, -Se-, -Te-, -SO- or -SO2-; R4 and R5 are each independently selected from H, C1-C 30 Alkyl or C6-C 30 of aromatic groups.

7. A boron-containing compound, characterized in that: The boron-containing compound is selected from at least one of the compounds shown in the following structural formula:

8. An electroluminescent device, characterized in that The invention comprises an anode, a cathode, and a light-emitting layer located between the anode and the cathode, wherein the light-emitting layer comprises the compound according to any one of claims 1 to 7.

9. A display panel, characterized in that: The display panel comprises the compound according to any one of claims 1 to 7 or the electroluminescent device according to claim 8.

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