Boron-containing compound and application thereof

Abstract

The invention relates to a boron-containing compound and application thereof. The boron-containing compound provided by the invention has a structure as shown in the following formula I. When the boron-containing compound is applied to the organic electroluminescent device as a blue light-emitting material, the organic electroluminescent device has lower driving voltage and higher current efficiency and service life at the same time. # imgabs0 #

Description

Technical Field

[0001] The present application belongs to the technical field of organic electroluminescence, and specifically relates to a boron-containing compound and the application of the compound in an organic electroluminescent device. Background Art

[0002] Organic electroluminescent display is known as the "third display technology revolution" because of its advantages such as self-luminescence, wide viewing angle, high contrast, fast response, low power consumption, lighter and thinner, power-saving, and flexible display. It is widely used in display and lighting fields such as mobile phones, televisions, computers, and cars.

[0003] With the development of organic electroluminescent materials, red and green light materials have basically met the needs of display. However, blue light materials are lagging behind red and green light in terms of efficiency and life due to their wide bandgap characteristics and difficulty in charge injection. However, the performance of blue light, especially deep blue light, has an important impact on improving display quality and reducing power consumption.

[0004] Blue light-emitting materials with commercial prospects require high efficiency and long life. Chinese patent application CN103222082 discloses an aromatic vinyl compound used as a blue electroluminescent material, but this compound has poor heat resistance and is easily cracked during the sublimation process. For example, a series of anthracene derivatives disclosed in Chinese patent CN1394195 can be used as OLED blue light materials, but the efficiency of such anthracene derivatives is low and cannot meet the current display requirements in practical applications. For another example, Chinese patent application CN101018760 discloses a series of aromatic amine derivatives, but due to the imbalance between their hole transport properties and electron transport properties, their service life is still not ideal. Therefore, the research and development of high-efficiency and long-life blue light-emitting materials is of great significance to promoting the development of organic electroluminescent display and lighting technology.

[0005] Therefore, the prior art still needs to be improved and developed. Summary of the invention

[0006] In view of the various defects and deficiencies in the prior art, the purpose of the present application is to provide a boron-containing compound as an organic electroluminescent blue light-emitting material. Therefore, the first aspect of the present application provides a boron-containing compound having a structure shown in Formula I:

[0007]

[0008] In Formula I, A 1 To A 16 are each independently selected from N or CR;

[0009] X 1 , X 2The same or different, each independently selected from O, S, Se, NR N 、CRaRb、(CRaRb) 2 , RaC=CRb or SiRaRb;

[0010] R, R N , Ra, Rb are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;

[0011] represents a single bond or a double bond;

[0012] The substituents used in the substitution are selected from deuterium, halogen, alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms or heteroaryl groups having 3 to 20 carbon atoms.

[0013] According to some embodiments of the present application, in Formula I, X 1 , X 2 Each independently selected from O, S, NR N , CRaRb or SiRaRb.

[0014] According to some embodiments of the present application, the number of substituents used in the substitution is 1, 2, 3 or 4.

[0015] According to some embodiments of the present application, the boron-containing compound has a structure shown in Formula 1 or Formula 2:

[0016]

[0017] In Formula 1 or Formula 2, A 1 To A9 , X 1 , X 2 The definition of is the same as that of formula I.

[0018] According to some embodiments of the present application, the boron-containing compound has a structure represented by Formula 1-1 to 1-8 or Formula 2-1 to Formula 2-8:

[0019]

[0020] In Formulas 1-1 to 1-8 or Formulas 2-1 to 2-8, A 1 To A 9 Each independently selected from N or CR, R, Ra, Rb, R N The definition is the same as that of formula I, R N1 and R N2 Same definition as R N .

[0021] According to some embodiments of the present application, the compound has a structure represented by Formula 1-1A to 1-8A or Formula 2-1A to Formula 2-8A:

[0022]

[0023] In Formula 1-1A to Formula 1-8A and Formula 2-1A to Formula 2-8A, A 7 To A 9 Each independently selected from N or CR, R, Ra, Rb, R N The definition is the same as that of formula I, R N1 and R N2 Same definition as R N In some embodiments, A 7 and A 9 Selected from CH, A 8 Selected from CR.

[0024] In some preferred embodiments, R in the boron-containing compound is selected from hydrogen, substituted or unsubstituted alkyl having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl having 3-10 carbon atoms, substituted or unsubstituted heteroalkyl having 1-10 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3-10 carbon atoms, substituted or unsubstituted alkoxy having 1-10 carbon atoms, substituted or unsubstituted aryl having 6-18 carbon atoms, substituted or unsubstituted alkenyl having 2-10 carbon atoms, substituted or unsubstituted alkynyl having 2-10 carbon atoms, and combinations thereof; the substituent used for the substitution is selected from deuterium, halogen, alkyl having 1-10 carbon atoms, cycloalkyl having 3-10 carbon atoms, aryl having 6-20 carbon atoms, or heteroaryl having 3-20 carbon atoms.

[0025] In some preferred embodiments, R in the boron-containing compound is selected from hydrogen, substituted or unsubstituted alkyl having 1-5 carbon atoms, substituted or unsubstituted cycloalkyl having 3-10 carbon atoms, substituted or unsubstituted alkoxy having 1-5 carbon atoms, substituted or unsubstituted heteroalkyl having 1-5 carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, and combinations thereof; the substituent used is selected from deuterium, halogen, alkyl having 1-10 carbon atoms, cycloalkyl having 3-10 carbon atoms, aryl having 6-20 carbon atoms, or heteroaryl having 3-20 carbon atoms.

[0026] In some preferred embodiments, R in the boron-containing compound is selected from hydrogen, substituted or unsubstituted methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, and combinations thereof; and the substituent used in the substitution is selected from deuterium.

[0027] In some preferred embodiments, Ra, Rb, R N , R N1 and R N2 is selected, at each occurrence, identically or differently, from the group consisting of: substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 10 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted aralkyl having 7 to 25 carbon atoms, substituted or unsubstituted alkoxy having 1 to 10 carbon atoms, substituted or unsubstituted aryloxy having 6 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted alkynyl having 2 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 25 carbon atoms The present invention relates to an aryl group having 1 to 20 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 10 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 10 carbon atoms, a substituted or unsubstituted amino group, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a hydroxyl group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and a combination thereof having 0 to 10 carbon atoms; the substituent used in the substitution is selected from deuterium, a halogen, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 3 to 20 carbon atoms.

[0028] In some preferred embodiments, Ra, Rb, R N , R N1 and R N2is selected, at each occurrence, identically or differently, from the group consisting of: substituted or unsubstituted aralkyl having 7 to 25 carbon atoms, substituted or unsubstituted aryloxy having 7 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 25 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms; the substitution being selected from deuterium, halogen, alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 20 carbon atoms or heteroaryl having 3 to 20 carbon atoms;

[0029] In some preferred embodiments, Ra, Rb, R N , R N1 and R N2 is selected, at each occurrence, identically or differently, from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dihydroindanyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted spirobifluorenyl; the substitution being selected from deuterium, halogen, alkyl having 1 to 6 carbon atoms (e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl), alkoxy having 1 to 6 carbon atoms (e.g. methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy or tert-butoxy), cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 12 carbon atoms (e.g. phenyl, tolyl or biphenyl) or heteroaryl having 3 to 10 carbon atoms.

[0030] In some preferred embodiments, Ra, Rb, R N , R N1 and R N2 Each is independently selected from the following structures and deuterated structures thereof:

[0031]

[0032] In some embodiments, the boron-containing compound has a structure shown in Formula 3 or Formula 4:

[0033]

[0034] In Formula 3 and Formula 4, R is defined as in Formula 1, R N1 and R N2 Same definition as R N .

[0035] In some embodiments, R is selected from hydrogen, substituted or unsubstituted alkyl having 1-5 carbon atoms, and the substituents used in the substitution are selected from deuterium or halogen. In some embodiments, R is selected from hydrogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl and combinations thereof; the substituents used in the substitution are selected from deuterium.

[0036] In some embodiments, R N1 and R N2 The same or different, each independently selected from the group consisting of: substituted or unsubstituted aralkyl having 7-25 carbon atoms, substituted or unsubstituted aryl having 6-25 carbon atoms; the substituents used in the substitution are selected from deuterium, halogen, alkyl having 1-6 carbon atoms, alkoxy having 1-6 carbon atoms or aryl having 6-12 carbon atoms.

[0037] In some embodiments, R N1 and R N2 the same or different, each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl; the substituents used in the substitution are selected from deuterium, halogen, alkyl groups having 1 to 4 carbon atoms (such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl) or aryl groups having 6 to 10 carbon atoms (such as phenyl or toluene).

[0038] In some embodiments, the number of substituents used in the substitution is 1, 2, 3 or 4.

[0039] In some embodiments, R N1 and R N2 Each is independently selected from the following structures and deuterated structures thereof:

[0040]

[0041] In some preferred embodiments, the boron-containing compound is selected from the compounds corresponding to number C1 to number C280:

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054]

[0055]

[0056]

[0057]

[0058] In a second aspect, the present application provides the use of the above-mentioned boron-containing compound in the preparation of an organic electroluminescent device.

[0059] According to some preferred embodiments of the present application, the boron-containing compound is used as a blue light doping material of a light-emitting layer in an organic electroluminescent device.

[0060] In some embodiments, the doping concentration (mass percentage) of the doping material is 1 wt% to 20 wt% relative to the host material in the light-emitting layer, for example, 2 wt%, 2.5 wt%, 3 wt%, 3.5 wt%, 4 wt%, 4.5 wt%, 5 wt%, 5.5 wt%, 6 wt%, 6.5 wt%, 7 wt%, 7.5 wt%, 8 wt%, 8.5 wt%, 9 wt%, 9.5 wt%, 10 wt%, 11 wt%, 12 wt%, 13 wt%, 14 wt%, 15 wt%, 16 wt%, 17 wt%, 18 wt%, 19 wt% or any value therebetween. In some embodiments, the doping concentration of the doping material is 1 wt% to 10 wt%. In some embodiments, the doping concentration of the doping material is 2 wt% to 8 wt%.

[0061] In a third aspect, the present application provides an organic electroluminescent device, which includes a light-emitting layer, wherein the doping material of the light-emitting layer contains the boron-containing compound described above in the present application.

[0062] According to some preferred embodiments of the present application, the organic electroluminescent device comprises: an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode. In some embodiments, the light-emitting layer further comprises a doping material.

[0063] According to some preferred embodiments of the present application, the organic electroluminescent device further comprises one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0064] In a fourth aspect, the present application provides a display component / device, which includes the boron-containing compound described in the first aspect of the present application or the organic electroluminescent device described in the third aspect of the present application. BRIEF DESCRIPTION OF THE DRAWINGS

[0065] Figure 1 It is a schematic diagram of an organic light-emitting device in a specific embodiment of the present application.

[0066] Figure 2 FIG. 4 is a schematic diagram of an organic light-emitting device in another specific embodiment of the present application.

[0067] The reference numerals are as follows:

[0068] 100. First organic light-emitting device, 101. Substrate, 110. Anode, 120. Hole injection layer, 130. Hole transport layer, 140. Electron blocking layer, 150. Light-emitting layer, 160. Hole blocking layer, 170. Electron transport layer, 180. Electron injection layer, 190. Cathode, 102. Encapsulation layer, 200. Second organic light-emitting device. DETAILED DESCRIPTION

[0069] The following specific examples are used to illustrate the technical solution of the present application, but are not used to limit the scope of the present application. Any other equivalent changes or modifications that are not deviated from the spirit disclosed in the present application should be included in the scope of the claims.

[0070] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1The first organic light-emitting device 100 is shown schematically and non-limitingly. The figure is not necessarily drawn to scale, and some layer structures in the figure can be omitted as needed. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, a light-emitting layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180 and a cathode 190. The device 100 can be manufactured by depositing the described layers in sequence. The properties and functions of each layer and exemplary materials are described in more detail in columns 6-10 of U.S. Patent US7,279,704B2, the entire contents of which are incorporated herein by reference.

[0071] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is one doped with F at a molar ratio of 50:1. 4

[0013] An example of an n-doped electron transport layer is BPhen doped with Li at a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety.

[0013] An example of an n-doped electron transport layer is BPhen doped with Li at a 1:1 molar ratio, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety.

[0013] U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg:Ag and an overlying transparent, conductive, sputter-deposited ITO layer. The principles and use of barrier layers are described in more detail in U.S. Patent No. 6,097,147 and U.S. Patent Application Publication No. 2003 / 0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. Patent Application Publication No. 2004 / 0174H6, which is incorporated by reference in its entirety. A description of protective layers can be found in U.S. Patent Application Publication No. 2004 / 0174H6, which is incorporated by reference in its entirety.

[0072] The above layered structure is provided by way of non-limiting example. The functions of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It can also include other layers not explicitly described. Within each layer, a single material or a mixture of multiple materials can be used to achieve optimal performance. Any functional layer can include several sublayers. For example, a light-emitting layer can have two layers of different light-emitting materials to achieve a desired light-emitting spectrum.

[0073] In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.

[0074] OLED also requires encapsulation layers, such as Figure 2 The second organic light emitting device 200 is schematically and non-limitingly shown. Figure 1 The difference is that an encapsulation layer 102 may also be included on the cathode 190 to prevent harmful substances from the environment, such as moisture and oxygen. Any material that can provide an encapsulation function can be used as an encapsulation layer, such as glass or an organic-inorganic hybrid layer. The encapsulation layer should be placed directly or indirectly on the outside of the OLED device. Multilayer thin film encapsulation is described in U.S. Pat. No. 7,968,146 B2, the entire contents of which are incorporated herein by reference.

[0075] Devices manufactured according to embodiments of the present application can be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of these consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and / or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet phones, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro displays, 3-D displays, vehicle displays, and taillights.

[0076] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0077] Definition of Substituent Terms

[0078] As used herein, the term "halogen or halide" includes fluorine, chlorine, bromine and iodine.

[0079] The term "alkyl" as used herein includes straight and branched alkyl groups. The alkyl group can be an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 12 carbon atoms, and more preferably an alkyl group having 1 to 6 carbon atoms. Examples of alkyl groups include, but are not limited to, methyl, ethyl, propyl, isobutyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. In addition, the alkyl group can be optionally substituted. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl and n-hexyl are preferred. In addition, the alkyl group can be optionally substituted.

[0080] As used herein, the term "alkenyl" is a straight chain, branched or cyclic non-aromatic hydrocarbon group containing one or more carbon-carbon double bonds. Alkenyl can be a straight chain, branched or cyclic non-aromatic hydrocarbon group having 2-20 carbon atoms and one or more carbon-carbon double bonds, preferably an alkenyl group having 2-12 carbon atoms, including but not limited to vinyl, propenyl, isopropenyl, 1-butenyl, 2-butenyl, isobutenyl, butadienyl, 1-pentenyl, 2-pentenyl, isopentenyl, 1,3-pentadienyl, 1,4-pentadienyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 1,3-hexadienyl, 1,4-hexadienyl, 1,5-hexadienyl, 2,4-hexadienyl or 1,3,5-hexatrienyl, etc. In addition, alkenyl can be optionally substituted.

[0081] The term "cycloalkyl" as used herein includes cyclic alkyl groups. The cycloalkyl group may be a cycloalkyl group having 3 to 20 ring carbon atoms, preferably a cycloalkyl group having 4 to 10 carbon atoms. Examples of cycloalkyl groups include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl, etc. Among the above, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl are preferred. In addition, the cycloalkyl group may be optionally substituted.

[0082] As used herein, term " heteroalkyl " comprises that one or more carbon atoms in alkyl chain are selected from the heteroatom replacement of the group consisting of nitrogen-atom, oxygen-atom, sulphur-atom, selenium-atom, phosphorus-atom, silicon-atom, germanium-atom and boron-atom. Heteroalkyl can be heteroalkyl with 1 to 20 carbon atoms, preferably heteroalkyl with 1 to 10 carbon atoms, more preferably heteroalkyl with 1 to 6 carbon atoms. The example of heteroalkyl includes methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminoindole, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisoindole, tert-butyldimethylsilyl, triethylsilyl, triisoindole, trimethylsilylmethyl, trimethylsilylethyl, trimethylsilylisoindole. Additionally, heteroalkyl groups can be optionally substituted.

[0083] The term "carbocyclyl" as used herein can be used interchangeably with "carbocycle" to refer to a non-aromatic saturated or partially unsaturated monocyclic or polycyclic ring system consisting of carbon atoms as ring atoms, and also includes an aromatic ring consisting of carbon atoms as ring atoms. In addition, the carbocyclyl can be optionally substituted.

[0084] The term "heterocyclic group" as used herein is used interchangeably with "heterocycle", "carboheterocyclic ring", and "carboheterocyclic group", and includes aromatic cyclic groups and non-aromatic cyclic groups. Aromatic cyclic groups include heteroaromatic cyclic groups having 3-18 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms, and boron atoms. Non-aromatic heterocyclic groups include saturated heterocyclic groups having 3-30 ring atoms and unsaturated non-aromatic heterocyclic groups having 3-30 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen atoms, oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, phosphorus atoms, germanium atoms, and boron atoms, and preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, including at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Examples of non-aromatic heterocyclic groups include oxirane, oxetanyl, tetrahydrofuranyl, tetrahydropyranyl, dioxolane, dioxanyl, aziridinyl, dihydropyrrolyl, tetrahydropyrrolyl, piperidinyl, oxazolidinyl, morpholinyl, piperazinyl, oxepinyl, thiol, azepine and tetrahydrothioxol. In addition, the heterocyclic group may be optionally substituted.

[0085] The term "aryl or aromatic group" as used herein includes both non-fused and fused systems. The aryl group may be an aryl group having 6 to 30 carbon atoms, preferably an aryl group having 6 to 20 carbon atoms, and more preferably an aryl group having 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenanthrene, fluorene, pyrene, Perylene and azulene, preferably phenyl, biphenyl, biphenyl, triphenylene, fluorene and naphthalene. In addition, aryl can be optionally substituted. Examples of non-condensed aryl include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p-(2-phenylpropyl)phenyl, 4'-methylbiphenyl, 4"-tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2,3-xylyl, 3,4-xylyl, 2,5-xylyl, mesitylene and m-quadrenyl. In addition, aryl can be optionally substituted.

[0086] The term "heteroaryl" as used herein includes non-fused and fused heteroaromatic groups of 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen atom, oxygen atom, sulfur atom, selenium atom, silicon atom, phosphorus atom, germanium atom and boron atom. Heteroaryl also refers to heteroaryl. The heteroaryl may be a heteroaryl having 3 to 30 carbon atoms, preferably a heteroaryl having 3 to 20 carbon atoms, and more preferably a heteroaryl having 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridoindole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indazine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoxazole, benzothiazole, quinoline, isoxazole, benzofuran, benzothi ...furan, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran, benzofuran Quinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothienopyridine, thienodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, borazole and aza analogs thereof. In addition, the heteroaryl group may be optionally substituted.

[0087] As used herein, the term "alkoxy" is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl or -O-heterocyclyl. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl and heterocyclyl are the same as described above. Alkoxy can be an alkoxy having 1 to 20 carbon atoms, preferably an alkoxy having 1 to 6 carbon atoms. Examples of alkoxy include methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy and ethoxymethyloxy. In addition, the alkoxy may be optionally substituted.

[0088] The term "aryloxy" as used herein is represented by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl are the same as those described above. The aryloxy may be an aryloxy having 6 to 30 carbon atoms, preferably an aryloxy having 6 to 20 carbon atoms. Examples of aryloxy include phenoxy and biphenyloxy. In addition, the aryloxy may be optionally substituted.

[0089] The term "aralkyl" as used herein encompasses aryl-substituted alkyl groups. The aralkyl group may be an aralkyl group having 7 to 30 carbon atoms, preferably an aralkyl group having 7 to 20 carbon atoms, and more preferably an aralkyl group having 7 to 13 carbon atoms. Examples of aralkyl groups include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthyl-ethyl, 2-β-naphthyl-ethyl, 1-β-naphthylisopropyl, 2-β-naphthylisopropyl, p-methylbenzyl, m-methylbenzyl ... substituted alkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl, arylalkyl,

[0090] The term "alkylsilyl or silyl" as used herein encompasses silyl groups substituted by the groups listed above for the alkyl group, specifically including: methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl and the like.

[0091] The term "arylsilyl group" used herein is meant to encompass a group consisting of any of the aforementioned aryl groups and silyl groups.

[0092] The term "aza" in the terms "azadibenzofuran, azadibenzothiophene" and the like as used herein refers to one or more CH groups in the corresponding aromatic fragment being replaced by a nitrogen atom. For example, azatriphenylene includes dibenzo[f,h]quinoline, dibenzo[f,h]quinoline and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-mentioned aza derivatives can be readily envisioned by one of ordinary skill in the art, and all such analogs are determined to be included in the terms described herein.

[0093] In the present disclosure, unless otherwise defined, when any one of the terms in the group consisting of the following is used, for example, substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxyl, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, it means that any one of alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxyl, ester, sulfinyl, sulfonyl and phosphino may be substituted by one or more selected from deuterium, halogen, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted The invention also includes but is not limited to substituted cycloalkyl having 3-20 ring carbon atoms, unsubstituted heteroalkyl having 1-20 carbon atoms, unsubstituted heterocyclyl having 3-20 ring atoms, unsubstituted aralkyl having 7-30 carbon atoms, unsubstituted alkoxy having 1-20 carbon atoms, unsubstituted aryloxy having 6-30 carbon atoms, unsubstituted alkenyl having 2-20 carbon atoms, unsubstituted alkynyl having 2-20 carbon atoms, unsubstituted aryl having 6-30 carbon atoms, unsubstituted heteroaryl having 3-30 carbon atoms, unsubstituted alkylsilyl having 3-20 carbon atoms, unsubstituted arylsilyl having 6-20 carbon atoms, unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof.

[0094] It should be understood that when describing a molecular fragment as a substituent or otherwise attached to another moiety, its name can be written according to whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or according to whether it is a whole molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying a substituent or attaching a fragment are considered equivalent.

[0095] In the compounds mentioned in the present disclosure, hydrogen atoms can be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen can also be replaced by their other stable isotopes. Due to its enhanced efficiency and stability of the device, the replacement of other stable isotopes in the compound may be preferred. In the compounds mentioned in the present disclosure, multiple substitution refers to the range of up to the maximum available substitution, including double substitution. When a substituent in the compound mentioned in the present disclosure represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituent existing in multiple available substitution positions can be the same structure or different structures.

[0096] In the compounds mentioned in the present disclosure, unless explicitly defined, for example, adjacent substituents can be optionally connected to form a ring, otherwise adjacent substituents in the compound cannot be connected to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally connected to form a ring, including both the situation where adjacent substituents can be connected to form a ring and the situation where adjacent substituents are not connected to form a ring. When adjacent substituents can be optionally connected to form a ring, the formed ring can be a monocyclic or polycyclic ring, as well as an alicyclic, heteroalicyclic, aromatic or heteroaromatic ring. In this statement, adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0097] The materials for specific layers in the organic light-emitting device described in this application can be used in combination with various other materials present in the device. The combination of these materials is described in detail in paragraphs 0132-0161 of U.S. Patent Application US2016 / 0359122M, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0098] The materials described herein as specific layers that can be used in organic light-emitting devices can be used in combination with a variety of other materials present in the device. For example, the compounds disclosed herein can be used in combination with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. The combination of these materials is described in detail in paragraphs 0080-0101 of U.S. Patent Application US2015 / 0349273M, the entire contents of which are incorporated herein by reference. The materials described or mentioned therein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can easily consult the literature to identify other materials that can be used in combination.

[0099] In the embodiment of material synthesis, unless otherwise stated, all reactions are carried out under nitrogen protection. All reaction solvents are anhydrous and used as they are from commercial sources. The synthetic product uses one or more conventional equipment in the art (including but not limited to Agilent's liquid chromatograph, liquid chromatography-mass spectrometer, gas chromatography-mass spectrometer, differential scanning calorimeter, fluorescence spectrophotometer, electrochemical workstation, sublimator, etc.), and the structure is confirmed and the characteristics are tested by methods well known to those skilled in the art. In the embodiment of the device, the characteristics of the device are also tested by methods well known to those skilled in the art using conventional equipment in the art (including but not limited to the evaporation machine produced by Nanjing Institute of Micro-Science, the optical test system and life test system produced by Suzhou Fushida, the ellipsometer produced by Wuhan Yiguang Technology, etc.). Since those skilled in the art are aware of the relevant contents such as the use of the above-mentioned equipment and the test method, the inherent data of the sample can be obtained with certainty and without being affected, so the above-mentioned relevant contents will not be elaborated in this patent.

[0100] The preparation method of the compounds of the present application is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0101] Synthesis Example 1: Synthesis of Compound C11

[0102]

[0103] The synthetic route is as follows:

[0104]

[0105] Specific synthesis steps:

[0106] (1) Under nitrogen protection, add 60 mL of tetrahydrofuran and 2.67 g of Mg to a dry 500 mL reaction bottle, heat to 60°C, add 2 g of benzyl bromide to initiate the reaction, and then continue to add 15.1 g of benzyl bromide in tetrahydrofuran to prepare a Grignard reagent. In another dry 500 mL reaction bottle, add 120 mL of tetrahydrofuran and 25.0 g of 2-bromobenzyl bromide, 7.2 g of anhydrous cuprous bromide, and 8.6 g of anhydrous lithium bromide under nitrogen protection, control the temperature at 40-45°C, filter out the magnesium chips from the prepared Grignard reagent and add it dropwise to the reaction solution, and continue to react for 5 hours after the addition is complete. Cool to room temperature, terminate the reaction with hydrochloric acid, wash with water until neutral, pass through a chromatography column, and perform vacuum distillation to obtain 16.9 g of intermediate C11-1 with a yield of 65%.

[0107] (2) Under nitrogen protection, add intermediate C11-1 (52.2 g, 200 mmol) and THF (400 mL) to a dry four-necked reaction bottle, cool to below -80°C while stirring, start to drop 2.5 M n-butyl lithium THF solution (96 ml), keep warm for 1 hour after the addition, and take samples for testing. After the lithium salt reaction is completed, add 48.4 g of bis(3-methoxyphenyl) ketone (CAS: 39193-85-6) THF solution below -80°C, keep the temperature below -80°C during the addition, keep warm for 1 hour after the addition is completed, and stir for 2 hours after the temperature rises naturally. Add 120 mL of 3 M hydrochloric acid below -0°C, stir for 1 hour, add ethyl acetate (400 mL) and water (400 mL) for extraction, combine the organic phases, dry with anhydrous magnesium sulfate, filter, and remove the solvent under reduced pressure. The obtained crude product was directly added with acetic acid (300 mL) and hydrochloric acid (3 mL), and stirring was started. The temperature was then gradually raised to reflux for reaction for 2 h. After the reaction was completed, the solid was directly filtered out and rinsed with ethanol (100 mL) to obtain 47.2 g of intermediate C11-2 as a white solid powder with a yield of 58%.

[0108] (3) Pyridine hydrochloride (115.0 g, 1 mol) was added to a 5L three-necked flask, heated to 150°C to dissolve the pyridine hydrochloride, and intermediate C11-2 (40.6 g, 100 mmol) was added and stirred. The mixture was heated to 202°C and the temperature was controlled at 200°C to 202°C for 3 h. The reaction solution was cooled to 50°C, 50 mL of saturated saline and 100 mL of ethyl acetate were added to the reaction system and stirred. The mixture was allowed to stand for separation, and the aqueous phase was extracted with ethyl acetate twice, 100 mL each time. The combined organic phases were washed once with 50 mL of saturated sodium chloride. The organic phase was dried with 20 g of anhydrous sodium sulfate for 30 minutes and the desiccant was filtered off. The organic phase was concentrated under reduced pressure to obtain an off-white solid. 50 mL of heptane was added to the mixture and the mixture was slurried at room temperature. The mixture was filtered with suction at room temperature and dried at 40°C to obtain 33.9 g of intermediate C11-3 with a yield of 89.5%.

[0109] (4) 3,5-Dibromo-4-chlorotert-butylbenzene (16.3 g, 50 mmol), intermediate C11-3 (28.4 g, 75 mmol) and potassium carbonate (27.6 g, 200 mmol) were dissolved in 150 mL of dimethylacetamide and stirred at 100° C. for 20 hours. 150 mL of toluene was added to dilute the reaction mixture, and H 2 The organic phase was separated, the aqueous phase was extracted twice with toluene, the organic phases were combined, and the organic phase was washed with H 2 O, dried over anhydrous magnesium sulfate for 30 minutes, and then filtered to remove the desiccant. The organic phase was concentrated under reduced pressure to obtain an off-white solid, which was slurried with ethanol, stirred for 20 minutes, and filtered. The obtained solid was vacuum dried at 50°C to obtain 21.2 g of yellow solid C11-4 with a yield of 78%.

[0110] (5) Under nitrogen protection, 250 mL of anhydrous o-xylene and intermediate C11-4 (21.2 g, 39.0 mmol) were added to the reaction flask, the temperature was lowered to 0°C, and 2.5 M butyl lithium (17.2 mL, 58.9 mmol) was slowly added. After 20 minutes, the mixture was stirred at room temperature for 1 hour. Boron tribromide (11.7 g, 46.8 mmol) was then added, and the mixture was stirred at room temperature for 30 minutes and at 45°C for 50 minutes. N,N-diisopropylethylamine (10.1 g, 78 mmol) was then added, the mixture was stirred at room temperature for 30 minutes, reacted at 130°C for 20 hours, and cooled to room temperature after the reaction was completed. The reaction solution was filtered, the filter cake was washed with toluene, and the solid was vacuum dried at 50°C. The solid was purified by column chromatography with 20 mL of dichloromethane to obtain 4.0 g of yellow solid C11 compound with a yield of 20%.

[0111] Product MS (m / e): 516; 1 H NMR (400 MHz, CDCl 3 ): δ7.30-7.23(m,4H),7.20(td,2H),7.14-7.10(ddt,2H),7.06(dd,2H),6 .95(td,2H),6.78(ddd,2H),6.66-6.60(dd,2H),2.97(d,4H),1.36(s,9H).

[0112] Example 2: Synthesis of Compound C16

[0113]

[0114] Specific synthesis steps:

[0115] Use compound (CAS:4877-77-4) instead A suitable material ratio was selected, and other raw materials and steps were the same as in Example 1 to obtain compound C16.

[0116] Product MS (m / e): 514; 1 H NMR (400 MHz, CDCl 3 ): δ7.45-7.37(m,4H),7.3-7.24(m,6H),6.99-6.91(m,4H),6.78(ddd,2H),6.66-6.60(dd,2H),1.36(s,9H).

[0117] Example 3: Synthesis of Compound C32

[0118]

[0119] Specific synthesis steps:

[0120] Use compound (CAS:2952643-48-8) instead A suitable material ratio was selected, and other raw materials and steps were the same as in Example 1 to obtain compound C32.

[0121] Product MS (m / e): 624. 1 H NMR (400 MHz, CDCl 3 ): δ7.56-7.47(m,6H),7.39(dd,2H),7.28(td,2H),7.22–7.16(m,4H),7.12(ddt,2H),7.08-7.02(m,4H),2.97(s,4H),1.35(s,9H).

[0122] Example 4: Synthesis of Compound C37

[0123]

[0124] Specific synthesis steps:

[0125] Use compound replace Use compound replace A suitable material ratio was selected, and other raw materials and steps were the same as in Example 1 to obtain compound C37.

[0126] Product MS (m / e): 622. 1 H NMR (400 MHz, CDCl 3 ): δ7.56-7.47(m,6H),7.43-7.37(m,6H),7.28(td,2H),7.25(s,2H),7.18(dd,2H),7.04(ddd,2H),6.97(dd,2H),1.34(s,9H).

[0127] Example 5: Synthesis of Compound C53

[0128]

[0129] The synthetic route is as follows:

[0130]

[0131] Specific synthesis steps:

[0132] (1) Under nitrogen protection, add intermediate C11-1 (52.2 g, 200 mmol) and THF (400 mL) to a dry three-necked reaction bottle, cool to below -80°C while stirring, start to drop 2.5 M n-butyl lithium THF solution (96 mL), keep warm for 1 h after the addition, and take samples for testing. After the lithium salt reaction is completed, add 68.0 g of bis(3-bromophenyl)methanone THF solution below -80°C, keep the temperature below -80°C during the addition, keep warm for 1 h, and stir for 2 h after the temperature rises naturally. 120 mL of 3M hydrochloric acid was added thereto at below -0°C, and the mixture was stirred for 1 hour. Ethyl acetate (500 mL) and water (500 mL) were added for extraction. The organic phases were combined, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Acetic acid (400 mL) and hydrochloric acid (3 mL) were directly added to the crude product, and stirring was started. The mixture was then gradually heated to reflux for reaction for 2 hours. After the reaction was completed, the solid was directly filtered to obtain the solid. The solid was rinsed with ethanol (100 mL) to obtain 55.47 g of intermediate C53-1 as a white solid powder with a yield of 55%.

[0133] (2) Under nitrogen protection, 1,3-dibromo-2-chloro-5-iodobenzene (39.6 g, 100 mmol), cyclopentylboronic acid (13.7 g, 120 mmol), anhydrous potassium carbonate (27.6 g, 200 mmol), palladium acetate (0.45 g), 300 mL toluene, 100 mL ethanol and 100 mL deionized water were added to a dry three-necked reaction bottle, and the temperature was raised to reflux and reacted for 5 h. After the reaction was completed, the temperature was lowered to room temperature, 200 mL of water was added, the liquid was separated, the aqueous phase was extracted with toluene, the organic phase was collected, column chromatography, recrystallization, and drying were performed to obtain 20.3 g C53-2, with a yield of 60%.

[0134] (3) Under nitrogen protection, 300 mL of xylene, aniline (9.3 g, 100 mmol), intermediate C53-2 (16.9 g, 50 mmol), sodium tert-butoxide (14.4 g, 150 mmol), tris(dibenzylideneacetone)dipalladium 0.18 g, and tri-tert-butylphosphine 0.22 g were added to a dry three-necked reaction bottle, and the temperature was slowly raised to 105-110° C. under stirring, and the reaction was carried out for 2 hours. After the reaction solution was cooled, 100 mL of water was added, the organic phase was washed with water until neutral, column chromatography, recrystallization, and drying to obtain 12.3 g of C53-3, with a yield of 68%.

[0135] (4) Under nitrogen protection, add 300 mL of xylene, intermediate C53-1 (25.2 g, 50 mmol), intermediate C53-3 (18.2 g, 50 mmol), sodium tert-butoxide (7.2 g, 75 mmol), tris(dibenzylideneacetone)dipalladium (0.09 g), and tri-tert-butylphosphine (0.11 g) to a dry three-necked reaction bottle. Slowly raise the temperature to 110°C, and after the temperature stabilizes, raise the temperature to 130°C and react for 6 hours. The reaction solution is cooled by 50°C, 100 mL of water is added, washed with water, column chromatographed, recrystallized, and dried to obtain 19.4 g of C53-4, with a yield of 55%.

[0136] (5) Under nitrogen protection, add 2500 mL of analytical pure xylene to a dry three-necked reaction bottle, stir and add intermediate C53-4 (14.1 g, 0.02 mol), heat to about 55°C, cool to -30°C after dissolution, replace with nitrogen three times, and drop 12 mL of 2 mol / L n-butyl lithium. Slowly heat to 75°C and react for 3 hours. Cool to -25°C, add 6.0 g (0.024 mol) of boron tribromide, slowly heat to 60°C and keep warm for 3 hours. Cool to -20°C, drop 4.6 g of N,N-diisopropylethylamine. Slowly heat to 80°C and keep warm for 1 hour, then heat to 130°C and react for 12 hours. Cool the reaction solution to 50°C, column chromatography, recrystallization, and drying to obtain 4.3 g of C53 product with a yield of 32%.

[0137] Product MS (m / e): 678. 1 H NMR (400 MHz, CDCl 3 ): δ7.39-7.30(m,6H),7.27(td,2H),7.21-7.16(m,4H),7.15-7.10(m,6H),7.06(dd ,2H),6.99(ddd,2H),6.82(ddd,4H),2.97(s,4H),2.71(ddt,1H),1.83-1.61(m,8H).

[0138] Example 6: Synthesis of Compound C58

[0139]

[0140] Specific synthesis steps:

[0141] Use compound replace By selecting a suitable material ratio, other raw materials and steps are the same as in Example 5 to obtain compound C58.

[0142] Product MS (m / e): 676. 1 H NMR (400 MHz, CDCl 3): δ7.46-7.38(m,4H),7.37-7.30(m,6H),7.30-7.23(m,4H),7.20-7.10(m,6H) ),7.02-6.94(m,4H),6.84-6.78(m,4H),2.75-2.67(m,1H),1.84-1.60(m,8H).

[0143] Example 7: Synthesis of Compound C102

[0144]

[0145] The synthetic route is as follows:

[0146]

[0147] Specific synthesis steps:

[0148] Use compound and Replacing C53-2 and The target compound C102 was obtained by selecting a suitable material ratio and referring to Example 5 for other raw materials and steps.

[0149] Product MS (m / e): 778; 1 H NMR (400 MHz, CDCl 3 ): δ7.35(dd,2H),7.30-7.23(m,6H),7.20(td,2H),7.12(m,2H),7.09-7.02(m, 6H),7.00-6.95(m,2H),6.88(dd,2H),6.86(dd,2H),2.97(d,4H),1.35(d,27H).

[0150] Example 8: Synthesis of Compound C104

[0151]

[0152] Use compound replace The target compound C104 was obtained by selecting a suitable material ratio and using the same other raw materials and steps as in Example 7.

[0153] Product MS (m / e): 676; 1 H NMR (400 MHz, CDCl 3): δ7.35(dd,2H),7.27(td,2H),7.20(td,2H),7.12(m,2H),7.06(dd,2H),7.01(ddd,2H),6.86(dd,2H),6.83(dd,2H),2.97(d,4H),1.36(s,9H).

[0154] Example 9: Synthesis of Compound C116

[0155]

[0156] Specific synthesis steps:

[0157] Use compound (CAS:92050-16-3) instead The target compound C116 was obtained by selecting a suitable material ratio and using the same other raw materials and steps as in Example 7.

[0158] Product MS (m / e): 886; 1 H NMR (400 MHz, CDCl 3 ): δ7.35(dd,2H),7.27(td,2H),7.20(td,2H),7.16-7.10(m,4H),7.06(dd,2H),7.01-6.92(m ,6H),6.88(dd,2H),6.83(dd,2H),2.97(d,4H),1.84-1.57(m,8H),1.36(s,9H),1.30(d,24H).

[0159] Example 10: Synthesis of Compound C145

[0160]

[0161] Specific synthesis steps:

[0162] Use compound replace Use compound replace The target compound C145 was obtained by selecting a suitable material ratio and using the same other raw materials and steps as in Example 7.

[0163] Product MS (m / e): 1116; 1 H NMR (400 MHz, CDCl 3): δ7.49(t,2H),7.39-7.31(m,8H),7.30-7.24(m,4H),7.24-7.16(m,4H),7.12(ddt,2H) ),7.06(dd,2H),6.97(ddd,2H),6.83(dd,2H),6.75(s,2H),2.97(d,4H),1.35(d,54H).

[0164] Example 11. Synthesis of Compound C170

[0165]

[0166] Specific synthesis steps:

[0167] Use compound replace Select appropriate material ratios, and refer to Examples 5 and 7 for other raw materials and steps to obtain compound C170.

[0168] Product MS (m / e): 776. 1 H NMR (400 MHz, CDCl 3 ): δ7.43(dd,2H),7.40(dd,2H),7.37-7.35(m,2H),7.29-7.23(m,8H),7.08 -7.02(m,4H),7.01-6.95(m,4H),6.88(dd,2H),6.83(dd,2H),1.35(d,27H).

[0169] Example 12. Synthesis of Compound C172

[0170]

[0171] Specific synthesis steps:

[0172] Use compound replace Use compound replace Select appropriate material ratios, and refer to Example 5 and Example 7 for other raw materials and steps to obtain compound C172.

[0173] Product MS (m / e): 674. 1 H NMR (400 MHz, CDCl 3): δ7.43(dd,2H),7.40(dd,2H),7.36(dd,2H),7.28(ddd,2H),7.25(s,2H),7.01(ddd,2H),6.97(dd,2H),6.89(dd,2H),6.83(dd,2H),1.36(s,9H).

[0174] Example 13. Synthesis of Compound C184

[0175]

[0176] Specific synthesis steps:

[0177] Use compound replace Use compound replace Select appropriate material ratios, and refer to Example 5 and Example 7 for other raw materials and steps to obtain the target compound C184.

[0178] Product MS (m / e): 884. 1 H NMR (400 MHz, CDCl 3 ): δ7.46-7.38(m,4H),7.37-7.32(m,2H),7.28(ddd,2H),7.25(s,2H),7.17-7.12(m,2H),7. 02-6.93(m,8H),6.88(dd,2H),6.83(dd,2H),1.84-1.57(m,8H),1.36(s,9H),1.30(d,24H).

[0179] Example 14. Synthesis of Compound C213

[0180]

[0181] Specific synthesis steps:

[0182] Use compound replace Use compound replace Use compound replace A suitable material ratio was selected, and other raw materials and steps were referred to Example 5 and Example 7 to obtain the target compound C213.

[0183] Product MS (m / e): 1114. 1 H NMR (400 MHz, CDCl 3): δ7.49(t,2H),7.46-7.20(m,20H),7.0-6.94(m,4H),6.83(dd,2H),6.75(s,2H),1.35(d,54H).

[0184] Example 15. Synthesis of Compound C220

[0185]

[0186] Specific synthesis steps:

[0187]

[0188] (1) Under nitrogen protection, add 300 mL of toluene, 4-tert-butylaniline (14.9 g, 100 mmol), 1-bromo-5-tert-butyl-2-chloro-3-methoxybenzene (27.8 g, 100 mmol), sodium tert-butoxide (14.4 g, 150 mmol), tris(dibenzylideneacetone)dipalladium 0.18 g, and 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl 0.47 g to a dry three-necked reaction bottle, slowly raise the temperature to 105-110°C under stirring, and react for 2 hours. After the reaction solution cools down, add 100 mL of water, wash the organic phase with water until neutral, column chromatography, recrystallize, and dry to obtain 30 g of C220-1 with a yield of 87%.

[0189] (2) Under nitrogen protection, add 300 mL of xylene, intermediate C53-1 (25.2 g, 50 mmol), intermediate C220-1 (17.3 g, 50 mmol), sodium tert-butoxide (7.2 g, 75 mmol), tri(dibenzylideneacetone)dipalladium (0.09 g), and tri-tert-butylphosphine (0.11 g) to a dry three-necked reaction bottle. Slowly raise the temperature to 110°C, and after the temperature stabilizes, raise the temperature to 130°C and react for 6 hours. The reaction solution is cooled by 50°C, 100 mL of water is added, washed with water, column chromatography, recrystallized, and dried to obtain 32.7 g of C220-2, with a yield of 85%.

[0190] (3) Add pyridine hydrochloride (57.5 g, 0.5 mol) to a 5L three-necked flask, heat to 150°C to dissolve pyridine hydrochloride, add intermediate C220-2 (38.5 g, 50 mmol) and start stirring. Continue heating to 202°C, control the temperature from 200°C to 202°C for 3 hours, and cool the reaction solution to below 50°C. Add 50 mL of saturated brine and 200 mL of ethyl acetate to the reaction system and stir. Let stand to separate the liquids. Extract the aqueous phase with ethyl acetate twice, 100 mL each time, and wash the combined organic phases with 50 mL of saturated sodium chloride once. Dry the organic phase with 20 g of anhydrous sodium sulfate for 30 minutes and filter out the desiccant. Concentrate the organic phase under reduced pressure to obtain an off-white solid. Add 100 mL of heptane to slurry at room temperature, filter at room temperature, and dry at 40°C to obtain 31.7 g of intermediate C220-3, with a yield of 84%.

[0191] (4) Intermediate C220-3 (37.6 g, 50 mmol) and potassium carbonate (13.8 g, 100 mmol) were dissolved in 150 mL of dimethylacetamide and stirred at 100 °C for 20 hours. 100 mL of toluene was added to dilute the reaction mixture, and H 2 The organic phase was separated, the aqueous phase was extracted twice with toluene, the organic phases were combined, and the organic phases were washed with H 2 O, dried over anhydrous magnesium sulfate for 30 minutes, and then filtered to remove the desiccant. The organic phase was concentrated under reduced pressure to obtain an off-white solid, which was slurried with ethyl acetate, stirred for 20 minutes, and filtered. The obtained solid was vacuum dried at 50°C to obtain a yellow solid C220-427.6 g with a yield of 82%.

[0192] (5) Under nitrogen protection, 250 mL of anhydrous o-xylene and intermediate C220-4 (26.3 g, 39.0 mmol) were added to the reaction flask, the temperature was lowered to 0°C, and 2.5 M butyl lithium (17.2 mL, 58.9 mmol) was slowly added. After 20 minutes, the mixture was stirred at room temperature for 1 hour. Boron tribromide (11.7 g, 46.8 mmol) was then added, and the mixture was stirred at room temperature for 30 minutes and at 45°C for 50 minutes. N,N-diisopropylethylamine (10.1 g, 78 mmol) was then added, the mixture was stirred at room temperature for 30 minutes, reacted at 130°C for 20 hours, and cooled to room temperature after the reaction was completed. The reaction solution was cooled to 50°C, column chromatography, recrystallization, and drying to obtain 7.8 g of C220 product with a yield of 31%.

[0193] Product MS (m / e): 647. 1 H NMR (400 MHz, CDCl 3): δ7.36(dd,1H),7.27(m,5H),7.20(td,2H),7.12(ddt,2H),7.09-7.02(m,4H),6.9 9(dd,1H),6.94(dd,1H),6.88(d,1H),6.83(dd,1H),6.78(dd,1H),6.58(d,1H),3.01 -2.87(m,4H),1.34(d,18H).

[0194] Example 16. Synthesis of Compound C258

[0195]

[0196] Specific synthesis steps:

[0197]

[0198] (1) Under nitrogen protection, add 300 mL of toluene, 4-tert-butylaniline (14.9 g, 100 mmol), 1-bromo-5-tert-butyl-2-chloro-3-iodobenzene (37.3 g, 100 mmol), sodium tert-butoxide (14.4 g, 150 mmol), tris(dibenzylideneacetone)dipalladium 0.18 g, and 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl 0.47 g to a dry three-necked reaction bottle, slowly raise the temperature to 105-110°C while stirring, and react for 2 hours. After the reaction solution cools down, add 100 mL of water, wash the organic phase with water until neutral, column chromatography, recrystallize, and dry to obtain 32.7 g of C258-1, with a yield of 83%.

[0199] (2) Under nitrogen protection, add 300 mL of toluene, 3',5,5'-tri-tert-butyl-[1,1'-biphenyl]-2-amine (16.9 g, 50 mmol), intermediate C258-1 (19.8 g, 50 mmol), sodium tert-butoxide (7.2 g, 75 mmol), tris(dibenzylideneacetone)dipalladium 0.18 g, and 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl 0.47 g to a dry three-necked reaction bottle. Slowly raise the temperature to 105-110°C while stirring, and react for 2 hours. The reaction solution is cooled by 50°C, 100 mL of water is added, washed with water, column chromatographed, recrystallized, and dried to obtain 27.3 g of C258-2, with a yield of 84%.

[0200] (3) Under nitrogen protection, add 300 mL of xylene, intermediate C53-1 (25.2 g, 50 mmol), intermediate C258-2 (32.6 g, 50 mmol), sodium tert-butoxide (7.2 g, 75 mmol), tris(dibenzylideneacetone)dipalladium (0.09 g), and tri-tert-butylphosphine (0.11 g) to a dry three-necked reaction bottle. Slowly raise the temperature to 110°C, and after the temperature stabilizes, raise the temperature to 130°C and react for 6 hours. The reaction solution is cooled by 50°C, 100 mL of water is added, washed with water, column chromatographed, recrystallized, and dried to obtain 29.8 g of C258-3, with a yield of 60%.

[0201] (4) Under nitrogen protection, 250 mL of anhydrous o-xylene and intermediate C258-3 (38.7 g, 39.0 mmol) were added to the reaction flask, the temperature was lowered to 0°C, and 2.5 M butyl lithium (17.2 mL, 58.9 mmol) was slowly added. After 20 minutes, the mixture was stirred at room temperature for 1 hour. Boron tribromide (11.7 g, 46.8 mmol) was then added, and the mixture was stirred at room temperature for 30 minutes and at 45°C for 50 minutes. N,N-diisopropylethylamine (10.1 g, 78 mmol) was then added, the mixture was stirred at room temperature for 30 minutes, reacted at 130°C for 20 hours, and cooled to room temperature after the reaction was completed. The reaction solution was cooled to 50°C, column chromatographed, recrystallized, and dried to obtain 11.6 g of C258 product with a yield of 30%.

[0202] Product MS (m / e):966. 1 H NMR (400 MHz, CDCl 3 ): δ7.49(t,1H),7.39-7.23(m,10H),7.23-7.16(m,3H),7.12(ddt,2H),7.09-7.02(m,4H) ,6.98-6.95(ddd,2H),6.88(dd,2H),6.83(dd,2H),3.01-2.87(m,4H),1.38-1.32(m,45H).

[0203] Example 17. Synthesis of Compound C280

[0204]

[0205] Specific synthesis steps:

[0206] (1) Referring to Example 1 and Example 5 The synthetic route using the compound replace Use compound replace Selecting the appropriate material ratio and reaction conditions can obtain the intermediate

[0207] (2) Use compound replace Use compound replace A suitable material ratio was selected, and other raw materials and steps were referred to Example 16 to obtain the target compound C280.

[0208] Product MS (m / e): 944. 1 H NMR (400 MHz, CDCl 3 ): δ7.36(dd,2H),7.30-7.24(m,2H),7.17-7.09(m,5H),7.07-7.02(m,2H),7.02-6.95(m,6 H),6.88(dd,2H),6.83(dd,2H),2.96-2.80(m,4H),1.84-1.57(m,4H),1.38-1.30(m,48H).

[0209] Those skilled in the art should be aware that the above preparation method is only an illustrative example, and those skilled in the art can obtain other compound structures of the present application by improving it.

[0210] Device Example 1

[0211] First, the glass substrate with a 120nm thick indium tin oxide (ITO) anode was cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate was dried in a nitrogen-filled glove box to remove moisture, and then the substrate was mounted on a substrate holder and loaded into a vacuum chamber. The organic layers specified below were placed in a vacuum of approximately 10 -8 Torr's case The ITO anode was deposited sequentially by thermal vacuum deposition at a rate of 1.5 %. At the same time, the compounds HT and HI (weight ratio 97:3) were evaporated as a hole injection layer (HIL) with a thickness of Compound HT was used as a hole transport layer (HTL) with a thickness of Compound EB is used as an electron blocking layer (EBL) with a thickness of Then, BH as the blue light host and the compound C11 of the present application as the dopant (weight ratio 98:2) were co-evaporated to form an emitting layer (EML) with a thickness of Compound HB was used as the hole blocking layer (HBL) with a thickness of On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated (weight ratio 50:50) as an electron transport layer (ETL) with a thickness of Finally, evaporation 8-Hydroxyquinoline-lithium (Liq) was used as an electron injection layer (EIL) and evaporated The device was then transferred back to the glove box and encapsulated with a glass lid to complete the device.

[0212] Device Example 2 to Device Example 17

[0213] The method is the same as that in device embodiment 1, the only difference is that the compounds C16, C32, C37, C53, C58, C102, C104, C116, C145, C170, C172, C184, C213, C220, C258 and C280 of the present application are used instead of the compound C11 of the present application as doping materials in the light-emitting layer (EML).

[0214] Device Comparison Example 1

[0215] The method is the same as that of device embodiment 1, except that compound A is used instead of compound C11 of the present application as the doping material in the light-emitting layer (EML).

[0216] The material structure used in the device is shown below:

[0217]

[0218] Table 1 lists the 2 Under the conditions, the voltage (V), external quantum efficiency (EQE) and lifetime (T) were measured. In order to better show the data comparison, the voltage, efficiency and lifetime of Comparative Example 1 were set to 100%, respectively, and the voltage, efficiency and lifetime data of Device Examples 1 to Device Examples 17 were converted relative to the corresponding data of Comparative Example 1. The relevant data and conversion results are shown in Table 1.

[0219] Table 1

[0220]

[0221]

[0222] Discussion: As shown in Table 1, at 10 mA / cm 2Under current density, the voltage of device embodiments 1 to device embodiments 17 can be reduced by 0 to 18% relative to comparative example 1, the external quantum efficiency is increased by 2% to 30%, and the device life is extended by up to 28%. The above data show that the compound of the present application, which has a seven-membered spiro ring structure and a boron-containing heteroaromatic ring structure connected by a specific structure, has a lower driving voltage and higher current efficiency and life compared with the comparative example compound A due to the introduction of the seven-membered spiro ring structure in the structure. This structural change brings about excellent device effects and unexpectedly proves the unique advantages of the compounds of the present application.

[0223] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the application. Therefore, as will be apparent to those skilled in the art, the claimed application may include variations of the specific embodiments and preferred embodiments described herein. Many of the materials and structures described herein may be replaced with other materials and structures without departing from the spirit of the application. It should be understood that the various theories about why the application works are not intended to be restrictive.

Claims

1. A boron-containing compound having a structure as shown in the following formula I: In Formula I, A1 to A 16 are each independently selected from N or CR; X1 and X2 are the same or different and are independently selected from O, S, Se, NR N , CRaRb, (CRaRb)2, RaC=CRb or SiRaRb; preferably, X1 and X2 are each independently selected from O, S, NR N , CRaRb or SiRaRb; R, R N , Ra, Rb are selected, at each occurrence, identically or differently, from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2-20 carbon atoms, substituted or unsubstituted alkynyl having 2-20 carbon atoms, substituted or unsubstituted aryl having 6-30 carbon atoms, substituted or unsubstituted heteroaryl having 3-30 carbon atoms, substituted or unsubstituted alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof; represents a single bond or a double bond; The substituents used in the substitution are selected from deuterium, halogen, alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, cycloalkyl groups having 3 to 10 carbon atoms, aryl groups having 6 to 20 carbon atoms or heteroaryl groups having 3 to 20 carbon atoms.

2. The boron-containing compound according to claim 1, characterized in that The boron-containing compound has a structure shown in Formula 1 or Formula 2: In Formula 1 and Formula 2, A1 to A9 are each independently selected from N or CR, and X1 and X2 are defined as in Formula 1; Preferably, the boron-containing compound has a structure represented by Formula 1-1 to 1-8 or Formula 2-1 to Formula 2-8: In Formulae 1-1 to 1-8 and Formulae 2-1 to 2-8, A1 to A9 are each independently selected from N or CR, R, Ra, Rb, R N The definition is the same as that of formula I, R N1 and R N2 Same definition as R N ; More preferably, the boron-containing compound has a structure represented by Formula 1-1A to 1-8A or Formula 2-1A to Formula 2-8A: In Formulae 1-1A to 1-8A and 2-1A to 2-8A, A7 to A9 are each independently selected from N or CR, R, Ra, Rb, R N The definition is the same as that of formula I, R N1 and R N2 Same definition as R N , preferably, A7 and A9 are selected from CH, and A8 is selected from CR.

3. The boron-containing compound according to claim 1 or 2, characterized in that R is selected from hydrogen, substituted or unsubstituted alkyl having 1-10 carbon atoms, substituted or unsubstituted cycloalkyl having 3-10 carbon atoms, substituted or unsubstituted heteroalkyl having 1-10 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3-10 carbon atoms, substituted or unsubstituted alkoxy having 1-10 carbon atoms, substituted or unsubstituted aryl having 6-18 carbon atoms, substituted or unsubstituted alkenyl having 2-10 carbon atoms, substituted or unsubstituted alkynyl having 2-10 carbon atoms and combinations thereof; the substituents used in the substitution are selected from deuterium, halogen, alkyl having 1-10 carbon atoms, cycloalkyl having 3-10 carbon atoms, aryl having 6-20 carbon atoms or heteroaryl having 3-20 carbon atoms; Preferably, R is selected from hydrogen, substituted or unsubstituted alkyl having 1-5 carbon atoms, substituted or unsubstituted cycloalkyl having 3-10 carbon atoms, substituted or unsubstituted alkoxy having 1-5 carbon atoms, substituted or unsubstituted heteroalkyl having 1-5 carbon atoms, substituted or unsubstituted aryl having 6-12 carbon atoms, and combinations thereof; the substituents used in the substitution are selected from deuterium, halogen, alkyl having 1-10 carbon atoms, cycloalkyl having 3-10 carbon atoms, aryl having 6-20 carbon atoms, or heteroaryl having 3-20 carbon atoms; More preferably, R is selected from hydrogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted cyclopropyl, substituted or unsubstituted cyclobutyl, substituted or unsubstituted cyclopentyl, substituted or unsubstituted cyclohexyl, substituted or unsubstituted adamantyl, substituted or unsubstituted phenyl and combinations thereof; and the substituents used in the substitution are selected from deuterium.

4. The boron-containing compound according to any one of claims 1 to 3, characterized in that Ra, Rb, R N , R N1 and R N2 is selected, at each occurrence, identically or differently, from the group consisting of: substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 10 carbon atoms, substituted or unsubstituted heterocycloalkyl having 3 to 10 carbon atoms, substituted or unsubstituted aralkyl having 7 to 25 carbon atoms, substituted or unsubstituted alkoxy having 1 to 10 carbon atoms, substituted or unsubstituted aryloxy having 6 to 20 carbon atoms, substituted or unsubstituted alkenyl having 2 to 10 carbon atoms, substituted or unsubstituted alkynyl having 2 to 10 carbon atoms, substituted or unsubstituted cycloalkyl having 6 to 25 carbon atoms substituted or unsubstituted heteroaryl having 3-20 carbon atoms, substituted or unsubstituted alkylsilyl having 3-10 carbon atoms, substituted or unsubstituted arylsilyl having 6-10 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino and combinations thereof having 0-10 carbon atoms; the substituents used in the substitution are selected from deuterium, halogen, alkyl having 1-10 carbon atoms, alkoxy having 1-10 carbon atoms, cycloalkyl having 3-10 carbon atoms, aryl having 6-20 carbon atoms or heteroaryl having 3-20 carbon atoms; Preferably, Ra, Rb, R N , R N1 and R N2 is selected, at each occurrence, identically or differently, from the group consisting of: substituted or unsubstituted aralkyl having 7 to 25 carbon atoms, substituted or unsubstituted aryloxy having 7 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 25 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms; the substitution being selected from deuterium, halogen, alkyl having 1 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 20 carbon atoms or heteroaryl having 3 to 20 carbon atoms; More preferably, Ra, Rb, R N , R N1 and R N2 is selected, at each occurrence, identically or differently, from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted dihydroindanyl, substituted or unsubstituted naphthobenzofuranyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted spirobifluorenyl; the substitution being selected from deuterium, halogen, alkyl having 1 to 6 carbon atoms, alkoxy having 1 to 6 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 12 carbon atoms or heteroaryl having 3 to 10 carbon atoms; More preferably, Ra, Rb, R N , R N1 and R N2 Each is independently selected from the following structures and deuterated structures thereof:

5. The boron-containing compound according to any one of claims 1 to 4, characterized in that The boron-containing compound has a structure shown in Formula 3 or Formula 4: In Formula 3 and Formula 4, R is defined as in Formula 1, R N1 and R N2 Same definition as R N ; Preferably, R is selected from hydrogen, substituted or unsubstituted alkyl having 1-5 carbon atoms, the substituent used in the substitution is selected from deuterium or halogen, preferably R is selected from hydrogen, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, substituted or unsubstituted isopropyl, substituted or unsubstituted butyl, substituted or unsubstituted isobutyl, substituted or unsubstituted tert-butyl and combinations thereof; the substituent used in the substitution is selected from deuterium; Preferably R N1 and R N2 The same or different, each independently selected from the group consisting of: substituted or unsubstituted aralkyl having 7-25 carbon atoms, substituted or unsubstituted aryl having 6-25 carbon atoms; the substituents used in the substitution are selected from deuterium, halogen, alkyl having 1-6 carbon atoms, alkoxy having 1-6 carbon atoms or aryl having 6-12 carbon atoms; More preferably, R N1 and R N2 The same or different, each independently selected from the group consisting of: substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted tetrahydronaphthyl; the substituents used in the substitution are selected from deuterium, halogen, alkyl having 1 to 4 carbon atoms or aryl having 6 to 10 carbon atoms; More preferably, R N1 and R N2 Each is independently selected from the following structures and deuterated structures thereof:

6. The boron-containing compound according to any one of claims 1 to 5, characterized in that The boron-containing compound is selected from the group consisting of the following compounds:

7. Use of the boron-containing compound according to any one of claims 1 to 6 in the preparation of an organic electroluminescent device.

8. An organic electroluminescent device, comprising: an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode; The light-emitting layer further comprises a doping material, wherein the doping material of the light-emitting layer comprises the boron-containing compound according to any one of claims 1 to 6; Preferably, the boron-containing compound is used as a blue light doping material of a light-emitting layer in an organic electroluminescent device.

9. The organic electroluminescent device according to claim 8, characterized in that: The doping concentration of the doping material is 1 wt% to 20 wt%, preferably 1 wt% to 10 wt%, and more preferably 2 wt% to 8 wt%, relative to the host material in the light-emitting layer.

10. A display component / device comprising the compound according to any one of claims 1 to 6 or the organic electroluminescent device according to claim 8 or 9.

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