Heterocyclic compound and application thereof

Abstract

The invention provides a heterocyclic compound and application thereof. The heterocyclic compound provided by the invention has a structure as shown in formula I, and can be used as a blue light emitting material of an organic electroluminescent device to improve the luminescent property of the device. # imgabs0 #

Description

Technical Field

[0001] The invention belongs to the technical field of organic electroluminescence, and specifically relates to a heterocyclic compound and 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 CN103222082A 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, Chinese patent application CN1394195A discloses a series of anthracene derivatives that 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 CN101018760A 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.

[0005] The research and development of high-efficiency and long-life blue luminescent materials is of great significance for promoting the development of organic electroluminescent display and lighting technology. The existing technology 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 object of the present invention is to provide a heterocyclic compound and its application. The heterocyclic compound of the present invention can be used as an organic electroluminescent blue host material to improve the luminescence performance of an organic electroluminescent device.

[0007] The first aspect of the present invention provides a heterocyclic compound having a structure shown in the following formula I:

[0008]

[0009] Among them, L A , L B , L Cand L D Each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof;

[0010] R A , R B , R C and R D Each is independently selected from a substituted or unsubstituted monocyclic nitrogen-containing heteroaryl group having 3 to 18 carbon atoms, and a substituted or unsubstituted polycyclic nitrogen-containing heteroaryl group having 6 to 30 carbon atoms;

[0011] n1, n2, n3 and n4 are each independently 0, 1, 2, 3 or 4, and n1, n2, n3 and n4 are not 0 at the same time;

[0012] represents a single bond or a double bond;

[0013] When L A , L B , L C , L D , R A , R B , R C and R D When there is a substituent, the substituent is one or more and each is independently selected from deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted deuterated alkyl having 1 to 20 carbon atoms, substituted or unsubstituted haloalkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted deuterated cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted halocycloalkyl 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 7 to 30 carbon atoms, The invention also includes an arylalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, an alkylsilyl group having 3 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an amino group having 0 to 20 carbon atoms, 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 combinations thereof.

[0014] In the present invention, n1 represents A Connected RA The number of n2 represents the number of L B Connected R B The number of n3 represents the number of L C Connected R C The number of n4 represents the number of L D Connected R D The number of .

[0015] In the present invention, the structure shown in Formula I can be expressed as the structure shown in Formula 1 or Formula 2 below:

[0016]

[0017] In Formula 1 and Formula 2, the definitions of the symbols are the same as in Formula 1.

[0018] According to some embodiments of the present invention, L A To L D Each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof.

[0019] According to some embodiments of the present invention, L A , L B , L C and L D Each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazolylene group, or a combination thereof.

[0020] According to some embodiments of the present invention, when L A , L B , L C and L D When there is a substituent, the substituent is one or more and each is independently selected from deuterium, halogen, alkyl having 1 to 10 carbon atoms, deuterated alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, deuterated cycloalkyl having 3 to 10 carbon atoms, halocycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 18 carbon atoms, heteroaryl having 3 to 18 carbon atoms, alkylsilyl having 3 to 10 carbon atoms, arylsilyl having 6 to 20 carbon atoms, and combinations thereof.

[0021] According to some embodiments of the present invention, L A , L B , L C and L D Each is independently selected from a single bond, a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of the following structures:

[0022]

[0023] Wherein, when the group W contains a substituent, the substituent is one or more and each is independently selected from deuterium, halogen, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkylsilyl group having 3 to 10 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, such as deuterium, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, trimethylsilyl and triphenylsilyl;

[0024] represents the position of connection to the benzene ring of the compound of formula I, Represents R A , R B , R C or R D The location of the connection.

[0025] According to some embodiments of the present invention, L A , L B , L C and L D Each is independently selected from the group consisting of a single bond or the following groups:

[0026]

[0027]

[0028] represents the position of connection to the benzene ring of the compound of formula I, Represents R A , R B , R C or R D The location of the connection.

[0029] According to some embodiments of the present invention, L A , L B , L C and L D Each is independently selected from the group consisting of a single bond or the following groups:

[0030]

[0031] represents the position of connection to the benzene ring of the compound of formula I, Represents R A , R B , R C or R D The location of the connection.

[0032] According to some embodiments of the present invention, L A , L B , L C and L D Each is independently selected from a single bond, a phenylene group, a deuterated phenylene group, a carbazolyl group, a benzene-substituted carbazolyl group, and combinations thereof. A , L B , L C and L D In some embodiments, L B is phenylene, deuterated phenylene or carbazolylene, L A , L C and L D All are single bonds.

[0033] According to some embodiments of the present invention, R A , R B , R C and R D Each is independently selected from a substituted or unsubstituted monocyclic nitrogen-containing heteroaryl group having 3 to 18 carbon atoms, and a substituted or unsubstituted polycyclic nitrogen-containing heteroaryl group having 12 to 30 carbon atoms.

[0034] In the present invention, R A , R B , R C and R D The number of nitrogen atoms in the monocyclic nitrogen-containing heteroaryl group and the polycyclic nitrogen-containing heteroaryl group is 1 to 4, preferably 1 to 3. The monocyclic nitrogen-containing heteroaryl group and the polycyclic nitrogen-containing heteroaryl group may also contain 1 to 4 other heteroatoms, such as O, S, Se, Si, etc.

[0035] According to some embodiments of the present invention, R A , R B , R C and R D Each is independently selected from a substituted or unsubstituted group Z, wherein the unsubstituted group Z is selected from the structures shown in the following formula III-1 to formula III-3;

[0036]

[0037] In formula III-1 and formula III-2, X is independently selected from a single bond, O, S, CR1R2 or SiR1R2; in formula III-3, X1, X2, X3 are each independently selected from CH and N, and at least one of X1, X2 and X3 is N;

[0038] R1 and R2 are each independently selected from hydrogen, deuterium, halogen, alkyl having 1-20 carbon atoms, deuterated alkyl having 1-20 carbon atoms, haloalkyl having 1-20 carbon atoms, cycloalkyl having 3-20 carbon atoms, deuterated cycloalkyl having 3-20 carbon atoms, halocycloalkyl having 3-20 carbon atoms, heteroalkyl having 1-20 carbon atoms, heterocycloalkyl having 3-20 carbon atoms, arylalkyl having 7-30 carbon atoms, arylalkyl having 1-20 carbon atoms, atom, an alkoxy group having 6-30 carbon atoms, an aryl group having 6-30 carbon atoms, an aryloxy group having 6-30 carbon atoms, a heteroaryl group having 3-30 carbon atoms, an alkenyl group having 2-20 carbon atoms, an alkynyl group having 2-20 carbon atoms, an alkylsilyl group having 3-20 carbon atoms, an arylsilyl group having 6-20 carbon atoms, an amino group having 0-20 carbon atoms, 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 combinations thereof;

[0039] When the group Z contains a substituent, the substituent is one or more and each is independently selected from deuterium, halogen, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a deuterated cycloalkyl group having 3 to 10 carbon atoms, a halocycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkylsilyl group having 3 to 10 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, and a combination thereof.

[0040] According to some embodiments of the invention, R1 and R2 are each independently selected from hydrogen, deuterium, an alkyl group having 1-10 carbon atoms, a deuterated alkyl group having 1-10 carbon atoms, a haloalkyl group having 1-10 carbon atoms, a cycloalkyl group having 3-10 carbon atoms, a deuterated cycloalkyl group having 3-10 carbon atoms, a halocycloalkyl group having 3-10 carbon atoms, an aralkyl group having 7-20 carbon atoms, an aryl group having 6-20 carbon atoms, and combinations thereof.

[0041] According to some embodiments of the invention, R1 and R2 are each independently selected from hydrogen, deuterium, alkyl having 1-6 carbon atoms, deuterated alkyl having 1-6 carbon atoms, halogenated alkyl having 1-6 carbon atoms, aryl having 6-15 carbon atoms, and combinations thereof.

[0042] According to some embodiments of the present invention, R1 and R2 are each independently selected from hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, isobutyl, phenyl, and combinations thereof. In some embodiments, R1 and R2 are each independently selected from hydrogen, deuterium, methyl and phenyl.

[0043] According to some embodiments of the present invention, the unsubstituted group Z is selected from the group consisting of the structures shown in the following formula:

[0044]

[0045]

[0046] Indicates that L A , L B , L C or L D The location of the connection.

[0047] In the present invention, when the group Z contains a substituent, the substituent is one or more and each is independently selected from deuterium, halogen, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkylsilyl group having 3 to 10 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, and a combination thereof; for example, the substituent is each independently selected from deuterium, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, trimethylsilyl, triphenylsilyl, N-phenylcarbazolyl, and a combination thereof.

[0048] According to some embodiments of the present invention, R A , R B , R C and R D Each is independently selected from the group consisting of the following structures:

[0049]

[0050]

[0051]

[0052] According to some embodiments of the present invention, the compound has the structure shown in the following formula I-1 to formula I-8:

[0053]

[0054] In Formula I-1 to Formula I-8, L A , L B , L C , L D , R A , R B , R C and R DThe definition of is the same as above, and n1, n2, n3 and n4 are each independently 1 or 2.

[0055] According to some embodiments of the present invention, the compound has a structure represented by Formula 1-1 to Formula 1-8 and Formula 2-1 to Formula 2-8:

[0056]

[0057] In Formulas 1-1 to 1-8 and 2-1 to 2-8, L A , L B , L C , L D , R A , R B , R C , R D , n1, n2, n3 and n4 are defined as above in this article.

[0058] According to some embodiments of the present invention, R A , R B , R C , R D Each is independently selected from the structures represented by the following formula 3-1 to formula 3-12:

[0059]

[0060]

[0061] In Formula 3-1 to Formula 3-12, X is selected from a single bond, O, S, CR1R2 or SiR1R2; Z1 and Z2 represent mono- or poly-substitution;

[0062] Z1, Z2, R1 and R2 are each independently selected from 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 aryl having 6 to 30 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 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 alkylsilyl having 3-20 carbon atoms, substituted or unsubstituted arylsilyl having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof having 0-20 carbon atoms; 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.

[0063] According to some preferred embodiments of the present invention, in Formulae 3-1 to 3-12, X is selected from a single bond or SiR1R2.

[0064] According to some embodiments of the present invention, in Formula 3-1 to Formula 3-12, Ar1 and Ar2 are each independently selected from hydrogen, a structure shown in Formula 4 or Formula 5:

[0065]

[0066] In Formula 4 and Formula 5, the definition of X is the same as that in Formula 3-1 to Formula 3-12;

[0067] Z1 to Z3 represent mono- or poly-substitution, and the definitions of Z1 to Z3 are the same as those of Z1 and Z2 in Formulae 3-1 to 3-12.

[0068] According to some preferred embodiments of the present invention, L A To L D Independently selected from a single bond, a phenylene group, a deuterated phenylene group, a pyridylene group, a pyrimidylene group, a triazineene group, a carbazolylene group, and combinations thereof.

[0069] In some preferred embodiments, Each is independently selected from the group consisting of:

[0070]

[0071]

[0072]

[0073] In some more preferred embodiments, Each is independently selected from the group consisting of:

[0074]

[0075] In some preferred embodiments, the compound is selected from the compounds corresponding to numbers C1 to C255:

[0076]

[0077]

[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095] In a second aspect, the present invention provides use of the above compound in preparing an organic electroluminescent device.

[0096] According to some embodiments of the present invention, the compound is used as a host material of a light-emitting layer in an organic electroluminescent device.

[0097] According to some preferred embodiments of the present invention, the compound is used as a blue light host material of a light-emitting layer in an organic electroluminescent device.

[0098] In a third aspect, the present invention provides an organic electroluminescent device, comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, wherein the main material of the light-emitting layer contains the above-mentioned compound of the present invention.

[0099] According to some embodiments of the present invention, the host material further contains a dopant. In some embodiments, the weight ratio of the compound of the present invention to the dopant is (80-100): (0-20). In some embodiments, the weight ratio of the compound of the present invention to the dopant is (90-99): (1-10). In some embodiments, the weight ratio of the compound of the present invention to the dopant is (95-99): (5-10).

[0100] According to some preferred embodiments of the present invention, the organic electroluminescent device further comprises one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, and an electron injection layer.

[0101] In a fourth aspect, the present invention provides a display component / device, which comprises the compound described in the first aspect of the present invention or the organic electroluminescent device described in the third aspect of the present invention. BRIEF DESCRIPTION OF THE DRAWINGS

[0102] Figure 1 FIG. 4 is a schematic diagram of an organic light-emitting device in a specific embodiment of the present invention.

[0103] Figure 2 FIG. 4 is a schematic diagram of an organic light-emitting device in another specific embodiment of the present invention.

[0104] The reference numerals are as follows:

[0105] 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

[0106] The technical scheme of the present invention is described in detail below through specific examples. The following examples are used to illustrate the present invention, but are not used to limit the scope of the present invention. Any other equivalent changes or modifications completed without departing from the spirit disclosed by the present invention should be included in the scope of the claims.

[0107] OLEDs can be manufactured on a variety of substrates, such as glass, plastic, and metal. Figure 1 The 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 US7279704B2, the entire contents of which are incorporated herein by reference.

[0108] There are more examples of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is m-MTDATA doped with F4-TCNQ at a molar ratio of 50:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. An example of a host material is disclosed in U.S. Patent No. 6,303,238 to Thompson et al., which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as disclosed in U.S. Patent Application Publication No. 2003 / 0230980, which is incorporated by reference in its entirety. 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 metal such as Mg:Ag with 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.

[0109] 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.

[0110] 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.

[0111] 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.

[0112] Devices manufactured according to embodiments of the present invention 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, heads-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.

[0113] The materials and structures described herein may also be used in other organic electronic devices listed above.

[0114] Definition of Substituent Terms

[0115] As used herein, the term "halogen or halide" includes fluorine, chlorine, bromine and iodine.

[0116] 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 10 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.

[0117] 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.

[0118] 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 3 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.

[0119] 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.

[0120] The term "heterocycloalkyl" as used herein is used interchangeably with "heterocyclic group", "heterocycle", "carbocyclic ring", and "carboheterocyclic group", and includes aromatic cyclic groups and non-aromatic cyclic groups. Aromatic cyclic groups include heteroaromatic ring 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, thiepineyl, azepineyl and tetrahydrothiazolyl. In addition, the heterocyclic group may be optionally substituted.

[0121] 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.

[0122] In this application, the term "arylene" refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from an "aryl". When the number of other groups connected to an arylene group is 0 (non-existent), the arylene group is considered an aryl group. For example, in Formula I, when L A is an arylene group, and L A The connected group R A When the number n1 = 0, L A Considered as aryl.

[0123] 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.

[0124] In this application, the term "heteroarylene" refers to a divalent or multivalent group formed by further losing one or more hydrogen atoms from a "heteroaryl". When the number of other groups connected to a heteroarylene group is 0 (non-existent), the heteroarylene group is considered a heteroaryl group. For example, in Formula I, when L A is a heteroarylene group, and L A The connected group R A When the number n1 = 0, L A Considered as heteroaryl.

[0125] 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.

[0126] 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.

[0127] 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,

[0128] 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.

[0129] The term "arylsilyl" as used herein is meant to encompass a group consisting of any of the aforementioned aryl groups and a silyl group, for example, triphenylsilyl.

[0130] 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.

[0131] 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.

[0132] 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.

[0133] In the compounds mentioned in this disclosure, hydrogen atoms may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. The replacement of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device.

[0134] In the compounds mentioned in the present disclosure, multiple substitution refers to the range including disubstitution up to the maximum number of available substitutions. When a substituent in the compounds mentioned in the present disclosure represents multiple substitutions (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can exist in multiple available substitution positions on its connection structure, and the substituents existing in multiple available substitution positions can be of the same structure or different structures.

[0135] 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.

[0136] The materials for specific layers in the organic light-emitting device described in the present invention 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.

[0137] 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.

[0138] 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.

[0139] The preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limitedly exemplified, and their synthetic routes and preparation methods are as follows:

[0140] Intermediate Synthesis Example:

[0141] Example 1: Synthesis of Intermediate M1

[0142]

[0143] (1) Under nitrogen protection, 600 ml of tetrahydrofuran and 158.75 g of 2-iodo-4-chlorobromobenzene were added to a 2-liter three-necked reaction flask. The temperature was cooled to -10°C to -5°C with stirring under nitrogen protection. 275 ml of a tetrahydrofuran solution of isopropylmagnesium chloride was added dropwise for about 1 hour. The temperature was kept at 0°C to -5°C for 1 hour. A solution prepared by controlling the temperature at 0°C to -5°C and 114.54 g of 2-methyl bromobenzene acetate and 150 ml of tetrahydrofuran was added dropwise for 1 hour. The temperature was naturally raised to room temperature and stirred for 8 hours. 100 ml of concentrated hydrochloric acid was added dropwise at a temperature below 0°C. The mixture was stirred for 5 minutes. 500 ml of ethyl acetate was added and the mixture was allowed to stand for separation. The organic phase was washed until neutral. The solvent was evaporated in vacuo. The residue was dissolved in 600 ml of n-heptane for crystallization. The residue was filtered and dried. The amount was 99.1 g. The yield was 51%. The product was recorded as S1.

[0144] (2) In a 2-liter three-necked reaction flask, 1 liter of ethylene glycol monoacetate, 18.55 g of potassium hydroxide, 20.38 g of hydrazine hydrate and 99.1 g of S1 were added. The mixture was stirred and heated to 160° C. to 170° C. for 8 hours. The reaction was completed under TLC monitoring. The temperature was lowered to room temperature, 100 ml of water and 500 ml of toluene were added, and the mixture was allowed to stand for separation. The organic phase was washed until neutral, and the solvent was evaporated in vacuo. The residue was dissolved in 150 ml of toluene and crystallized. The residue was filtered and dried. The product was 74.5 g in quantity and 78% in yield. The product was recorded as S2.

[0145] (3) 78.0 g of 2,2'-dibromobiphenyl and 500 ml of tetrahydrofuran were added to a 2L three-necked reaction flask, stirred, cooled to -70°C to -80°C under nitrogen protection, 100 ml of butyl lithium was added dropwise at -70°C to -80°C, and the temperature was kept at -70°C to -80°C for 1 hour, and a solution prepared by 42.5 g of tetrachlorosilane and 50 ml of tetrahydrofuran was added dropwise for about 0.5 hour. After the addition, the temperature was naturally raised to room temperature, acidified with 50 ml of concentrated hydrochloric acid, and 150 ml of ethyl acetate was added. The organic phase was washed until neutral, the solvent was evaporated in vacuo, 300 ml of heptane was added, the mixture was beaten for 0.5 hour, the temperature was lowered to room temperature, and filtered. The drying amount was 25.7 g, the yield was 41%, and the product was recorded as S3.

[0146] (4) 18.83 g of S2 and 200 ml of tetrahydrofuran were added to a 1 L three-necked reaction flask, stirred, cooled to -70°C to -80°C under nitrogen protection, 20 ml of butyl lithium was added dropwise at -70°C to -80°C, and the dripping was completed in about 0.5 hour. The temperature was kept at -70°C to -80°C for 0.5 hour, and a solution prepared by 12.55 g of S3 and 30 ml of tetrahydrofuran was added dropwise for about 0.5 hour. After the dripping was completed, the temperature was naturally raised to room temperature, acidified with 10 ml of concentrated hydrochloric acid, and 100 ml of ethyl acetate was added. The organic phase was washed until neutral, the solvent was evaporated in vacuo, 700 ml of heptane was added to dissolve, and passed through a 10 g silica gel column. The column liquid was concentrated to about 60 ml at normal pressure, cooled to room temperature, and filtered. The dried amount was 9.27 g, with a yield of 47%, and the product was recorded as M1.

[0147] Product MS (m / e): 394; 1 H NMR (400MHz, CDCl3): δ7.80(dd,2H),7.65-7.56(m,4H),7.48-7.38(m,6H),7.30-7.23(m,3H),3.13-2.95(m,4H).

[0148] Example 2: Synthesis of Intermediate M2

[0149]

[0150] Use compound replace Select appropriate material ratios, and other raw materials and steps are the same as in Example 1 to obtain intermediate M2. Product MS (m / e): 394.

[0151] Example 3: Synthesis of Intermediate M3

[0152]

[0153] Use compound replace Select appropriate material ratios, and other raw materials and steps are the same as in Example 1 to obtain intermediate M3. Product MS (m / e): 394.

[0154] Example 4: Synthesis of Intermediate M4

[0155]

[0156] (1) Raw materials replace Select a suitable material ratio, and the other raw materials and steps are the same as steps 1-2 of Example 1 to obtain S9;

[0157] (2) 141.5 g of 2-bromophenyl naphthalene alcohol ester, 156.5 g of 5-iodo-4-bromoanisole, 500 ml of toluene, 200 ml of anhydrous ethanol, 150 ml of water and 138 g of anhydrous potassium carbonate were added to a 2L three-necked reaction flask, and the mixture was replaced with nitrogen three times. Stirring was started, the temperature was raised to 70° C. to 75° C., and the reaction was kept warm for 24 hours. The mixture was cooled to room temperature, 100 ml of water was added, and the mixture was allowed to stand for separation. The organic phase was washed until neutral, the solvent was evaporated in vacuo, 900 ml of heptane was added, and the mixture was passed through a silica gel column. The solvent was evaporated in vacuo after the column liquid was passed through a silica gel column. 200 ml of anhydrous ethanol was added to dissolve the crystals, and the mixture was filtered and dried to obtain 85.5 g of a solid with a yield of 50%. The product was recorded as S10;

[0158] (3) 85.5 g of S10 and 500 ml of tetrahydrofuran were added to a 2 L three-necked reaction flask, stirred, cooled to -70°C to -80°C under nitrogen protection, 100 ml of butyl lithium was added dropwise at -70°C to -80°C, and the mixture was dripped over about 1 hour, kept at -70°C to -80°C for 1 hour, and a solution prepared by 42.5 g of tetrachlorosilane and 50 ml of tetrahydrofuran was added dropwise over about 0.5 hour, and the mixture was naturally heated to room temperature after dripping, acidified with 50 ml of concentrated hydrochloric acid, and 150 ml of ethyl acetate was added, and the organic phase was washed to neutrality, the solvent was evaporated in vacuo, 300 ml of heptane was added, and the mixture was beaten for 0.5 hour, cooled to room temperature, and filtered. The dried amount was 26 g, and the yield was 37%. The product was recorded as S11.

[0159] (4) 17.00 g of S9 and 150 ml of tetrahydrofuran were added to a 0.5 L three-necked reaction flask, stirred, cooled to -70°C to -80°C under nitrogen protection, 22 ml of butyl lithium was added dropwise at a temperature of -70°C to -80°C, and the mixture was finished after about 0.5 hour. The mixture was kept at -70°C to -80°C for 0.5 hour, and a solution prepared by adding 14.07 g of S11 and 30 ml of tetrahydrofuran was added dropwise for about 0.5 hour. After the addition, the mixture was naturally heated to room temperature, acidified with 8 ml of concentrated hydrochloric acid, and 50 ml of ethyl acetate was added. The organic phase was washed to neutrality, the solvent was evaporated in vacuo, 700 ml of heptane was added to dissolve, and the mixture was passed through a 15 g silica gel column. The column liquid was concentrated to about 60 ml at normal pressure, cooled to room temperature, and filtered. The dried product was 8.55 g, with a yield of 44%. The product was recorded as M4-1.

[0160] (5) 8.55 g of M4-1 and 100 ml of dichloromethane were added to a 0.5 L three-necked reaction flask, stirred, cooled to -15°C under nitrogen protection, and 5.52 g of boron tribromide was added dropwise at a temperature of -10°C to -15°C. The temperature was maintained at -10°C to -15°C, and the mixture was added dropwise for about 0.5 hours. After the addition was completed, the mixture was naturally heated to room temperature. TLC was performed on the plate, and there was no raw material. The mixture was hydrolyzed and separated. The organic phase was washed until neutral, the solvent was evaporated under normal pressure, 30 ml of heptane was added, and the mixture was slurried for 0.5 hours, and filtered. The dried product was 7.40 g, with a yield of 90%, and the product was recorded as M4-2.

[0161] (6) 7.40 g of M4-2, 2.34 g of pyridine, and 100 ml of dichloromethane were added to a 0.5 L three-necked flask, and the mixture was stirred. The temperature was lowered to -5°C under nitrogen protection, and 7.25 g of trifluoromethanesulfonic anhydride was added dropwise at a temperature of 0°C to -5°C. The temperature was maintained at about 0.5 hours, and the temperature was naturally raised to room temperature after the addition. The TLC plate was spotted, and there was no raw material. The liquid was separated, and the organic phase was washed until neutral. The solvent was evaporated under normal pressure, and 30 ml of anhydrous ethanol was added for crystallization, and the mixture was filtered. The dried product was 8.87 g, with a yield of 88%, and the product was recorded as M4.

[0162] Product MS (m / e): 508; 1 H NMR (400MHz, CDCl3): δ7.80(dd,1H),7.65-7.54(m,4H),7.51-7.33(m,6H),7.31-7.23(m,4H),3.14-2.94(m,4H).

[0163] Example 5: Synthesis of Intermediate M5

[0164]

[0165] (1) Use compound replace Select a suitable material ratio, refer to step 2 and step 3 of Example 4, and obtain S13;

[0166] (2) S13 reacts with S9. The synthesis scheme is as shown in step 4-6 of Example 4 to obtain intermediate M5. Product MS (m / e): 656.

[0167] Example 6: Synthesis of Intermediate M6

[0168]

[0169] Compound S2 was used to replace S9, and a suitable material ratio was selected. Other raw materials and steps were the same as those in Example 4 to obtain intermediate M6. Product MS (m / e): 542.

[0170] Example 7: Synthesis of Intermediate M7

[0171]

[0172] (1) Under nitrogen protection, 200 ml of toluene, 28.44 g of 1-bromo-2-bromomethyl-4-chlorobenzene and 26.2 g of triphenylphosphine were added to a 500 ml three-necked reaction flask, and the mixture was heated to 105° C. to 110° C. under stirring and refluxed for 8 hours. TLC showed that there was no starting material. The mixture was cooled to room temperature and filtered. The filter cake was washed twice with 100 ml of toluene*2. The solid was dried and the amount was 56.03 g. The yield was 96%. The product was recorded as S14.

[0173] (2) 56.03 g of S14, 11.1 g of 2-bromobenzaldehyde and 120 ml of tetrahydrofuran were added to a 500 ml three-necked reaction flask. The temperature was lowered to 0°C to -5°C under nitrogen protection. A solution prepared by 10.75 g of potassium tert-butoxide and 80 ml of tetrahydrofuran was added dropwise at a temperature of 0°C to -5°C for about 1 hour. The temperature was kept at 0°C to -5°C for 1 hour. TLC plate was spotted. No raw material was found. 20 ml of concentrated hydrochloric acid was added dropwise at a temperature below 0°C. The mixture was stirred for 5 minutes. 100 ml of ethyl acetate was added and the mixture was allowed to stand for separation. The organic phase was washed until neutral. The solvent was evaporated in vacuo. The residue was dissolved in 650 ml of the mixture and passed through a column at a temperature of 60°C. The column liquid was concentrated to 70 ml. The mixture was cooled to room temperature, filtered and dried. The amount was 18.75 g. The yield was 81%. The product was recorded as S15.

[0174] (3) Referring to step 4 of Example 1, compound S15 reacts with S3 to obtain intermediate M7.

[0175] Product MS (m / e): 392; 1 H NMR (400MHz, CDCl3): 7.81 (dd, 2H), 7.66-7.38 (m, 12H), 7.28 (ddd, 1H), 7.24 (s, 2H).

[0176] Example 8: Synthesis of Intermediate M8

[0177]

[0178] (1) Use compound replace Select a suitable material ratio, and the other raw materials and steps are the same as those in Example 7 to obtain intermediate S17;

[0179] (2) Referring to step 4-6 of Example 4, a suitable material ratio was selected, and S17 and S13 were reacted to obtain intermediate M8. Product MS (m / e): 654.

[0180] Example 9: Synthesis of Intermediate M9

[0181]

[0182] Referring to step 4-6 of Example 4, a suitable material ratio was selected, and S15 and S11 were reacted to obtain intermediate M9. Product MS (m / e): 540.

[0183] Compound synthesis example:

[0184] Synthesis Example 1: Synthesis of Compound C3

[0185]

[0186] The synthetic route is as follows:

[0187]

[0188] Specific synthesis steps:

[0189] 1L three-necked flask, equipped with magnetic stirring, after nitrogen replacement, add potassium tert-butoxide (11.2g, 0.1mol), D3 (33.2g, 0.1mol) and 400ml of toluene in sequence. After nitrogen replacement again, add (0.4g, 2mmol) tri-tert-butylphosphine and (0.2g, 1mmol) palladium acetate in sequence. After adding, heat to 85°C. Start to drop a solution consisting of (39.4g, 0.1mol) M1 and 100ml toluene, control the temperature at 80-120°C for 4 hours, and the reaction is completed. Adjust to neutral, separate the organic phase, extract, dry, column chromatography, spin dry the solvent, and obtain 48.3g of white solid with a yield of about 70%.

[0190] Product MS (m / e): 690; 1 H NMR (400MHz, CDCl3): δ8.15-8.08(m,3H),7.89(d,1H),7.81(dd,2H),7.71(d,1H),7.68-7.57(m,8H),7.49-7.23(m,15H),3.13-2.94(m,4H).

[0191] Synthesis Example 2: Synthesis of Compound C15

[0192]

[0193] The synthetic route is as follows:

[0194]

[0195] Specific synthesis steps:

[0196] (1) In a 1L reaction bottle, add M1 (55.29g, 140mmol), diboronic acid pinacol ester (42.66g, 168mmol) and toluene (600mL), fill with nitrogen and stir for 15 minutes, then add potassium acetate (41.22g, 420mmol), tris(dibenzylidene indeneacetone)dipalladium (2.59g), X-Phos (2.66g), heat and reflux for 3 hours, and the reaction is completed. Separate by silica gel short column chromatography, wash with hot toluene, desolventize the organic phase; hot ethanol slurry, and obtain 57.21g C15-1 off-white solid, with a yield of 84%.

[0197] (2) In a 1L reaction bottle, C15-1 (48.65 g, 100 mmol), 3-chlorobromobenzene-4d (19.55 g, 100 mmol), bis(triphenylphosphine)palladium dichloride (0.70 g, 1 mmol), potassium carbonate (27.64 g, 200 mmol), toluene (250 mL), ethanol (100 mL) and deionized water (100 mL) were added, and the temperature was raised to 80°C under nitrogen protection, and stirred for 4 hours; the reaction solution was cooled to room temperature, the organic phase was separated, dried over anhydrous magnesium sulfate, separated by silica gel column chromatography, and the organic phase was desolvated; recrystallized from n-heptane to obtain 37.06 g of C15-2 as an off-white solid, with a yield of 78%.

[0198] (3) Intermediate D1 was used to replace intermediate D3, C15-2 was used to replace M1, and a suitable material ratio was selected. The other raw materials and steps were the same as those in Synthesis Example 1 to obtain the target compound C15.

[0199] Product MS (m / e): 605; 1 H NMR (400MHz, CDCl3): δ8.18-8.10(m,2H),7.81(dd,2H),7.73(d,1H),7.69-7.56(m,5H),7.53-7.50(dd,1H),7.49 -7.23(m,12H),3.16-2.95(m,4H).

[0200] Synthesis Example 3: Synthesis of Compound C26

[0201]

[0202] The synthetic route is as follows:

[0203]

[0204] Specific synthesis steps:

[0205] (1) 3,6-dibromo-9H-carbazole was used to replace M1, D11 was used to replace D3, and a suitable material ratio was selected. The other raw materials and steps were the same as those in Synthesis Example 1 to obtain intermediate C26-1;

[0206] (2) Intermediate C26-1 was used to replace intermediate D3, and a suitable material ratio was selected. The other raw materials and steps were the same as those in Synthesis Example 1 to obtain compound C26.

[0207] Product MS (m / e): 1079. 1 H NMR (400MHz, CDCl3): δ8.05(d,2H),7.91(dd,3H),7.87-7.68(m,5H),7.67-7.56(m,6H),7.54-7. 50(d,2H),7.49-7.38(m,7H),7.35(dd,2H),7.29-7.20(m,6H),3.13-2.94(m,4H),1.35(s,36H).

[0208] Synthesis Example 4: Synthesis of Compound C35

[0209]

[0210] The synthetic route is as follows:

[0211]

[0212] Specific synthesis steps:

[0213] (1) 3-bromocarbazole was used to replace M1, triphenylsilyl chloride was used to replace D3, and a suitable material ratio was selected. The other raw materials and steps were the same as those in Synthesis Example 1 to obtain intermediate D26-1;

[0214] (2) 3-bromocarbazole and D26-1 were used to replace M1 and D3, respectively, and a suitable material ratio was selected. The other raw materials and steps were the same as those in Synthesis Example 1 to obtain intermediate D26;

[0215] (3) D26 was used to replace D3, and a suitable material ratio was selected. The other raw materials and steps were the same as those in Synthesis Example 1 to obtain the target compound C35; the product MS (m / e): 948.

[0216] Synthesis Example 5: Synthesis of Compound C66

[0217]

[0218] The synthetic route is as follows:

[0219]

[0220] Specific synthesis steps:

[0221] (1) 3-bromocarbazole and 10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasilicon are used to replace M1 and D3 respectively, and a suitable material ratio is selected. Other raw materials and steps are the same as those in Synthesis Example 1 to obtain intermediate D21;

[0222] (2) M3 and D21 were used to replace M1 and D3 respectively, and the appropriate material ratio was selected. The other raw materials and steps were the same as those in Synthesis Example 1 to obtain the target compound C66; product MS (m / e): 872.

[0223] Synthesis Example 6: Synthesis of Compound C96

[0224]

[0225] The synthetic route is as follows:

[0226]

[0227] Specific synthesis steps:

[0228] M2 and D15 were used to replace M1 and D3 respectively, and the appropriate material ratio was selected. The other raw materials and steps were the same as those in Synthesis Example 1 to obtain the target compound C96. Product MS (m / e): 802.

[0229] Synthesis Example 7: Synthesis of Compound C109

[0230]

[0231] The synthetic route is as follows:

[0232]

[0233] Specific synthesis steps:

[0234] (1) Under nitrogen protection, add M1 (19.4 g, 0.1 mol), diboric acid pinacol ester (30.5 g, 0.12 mol), potassium acetate (19.6 g, 0.2 mol), 0.3 g tris(dibenzylideneacetone)dipalladium, 0.3 g X-phos, 300 ml dioxane to a 2L three-necked flask, and heat to raise the temperature. Control the temperature at 104°C and reflux for 4 hours. The reaction solution is cooled to room temperature, 300 ml toluene and 300 ml water are added, stirred for 10 minutes, allowed to stand for separation, extracted, the organic phases are combined, washed with water until neutral, column chromatography, spin-dried solvent, 1:3 toluene:ethanol recrystallization, suction filtration, and drying to obtain 46.7 g of light yellow solid C109-1, with a yield of 96%.

[0235] (2) Under nitrogen protection, C109-1 (50.1 g, 0.103 mol), 9,9' (6-chloro-1,3,5-triazine-2,4-diyl) bis (9H-carbazole) (44.6 g, 0.1 mol), 0.1 g bis (triphenylphosphine) palladium dichloride, 200 ml toluene, 100 ml anhydrous ethanol were added to a 2L three-necked flask, and the temperature was raised. Anhydrous potassium carbonate (20.7 g, 0.15 mol) and 50 ml aqueous solution were added dropwise at a temperature of 70°C to 75°C. After the addition, the temperature was controlled at 70°C to 75°C and refluxed for 20 hours. The reaction solution was cooled to room temperature, filtered, slurried with ethanol twice, dissolved in toluene, column chromatography, and the solvent was spin-dried. Recrystallized with 4 times toluene and 4 times heptane, filtered, and dried to obtain 55.4 g white solid C109 with a yield of 72%.

[0236] Product MS (m / e): 769. 1 H NMR (400MHz, CDCl3): δ8.23(dd,4H),7.93(d,1H),7.80(d,2H),7.77-7.73(dd,4H),7.68-7.56(m,5H),7.50 -7.36(m,9H),7.35-7.24(m,6H),3.16-2.96(m,4H).

[0237] Synthesis Example 8: Synthesis of Compound C151

[0238]

[0239] The synthetic route is as follows:

[0240]

[0241] Specific synthesis steps:

[0242] (1) M4 was used instead of M1, and a suitable material ratio was selected. The other raw materials and steps were the same as those in step 1 of Synthesis Example 2 to obtain intermediate C151-1;

[0243] (2) C151-1 was used to replace C109-1, and a suitable material ratio was selected. The other raw materials and steps were the same as those in step 2 of Synthesis Example 7 to obtain the target compound C151. Product MS (m / e): 769.

[0244] Synthesis Example 9: Synthesis of Compound C157

[0245]

[0246] The synthetic route is as follows:

[0247]

[0248] Specific synthesis steps:

[0249] (1) M5 was used instead of M1, 2 times of biboric acid pinacol ester was used, and a suitable material ratio was selected. The other raw materials and steps were the same as those in step 1 of Synthesis Example 2 to obtain intermediate C157-1;

[0250] C157-1 and 2-chloro-4,6-diphenyl-1,3,5-triazine were used to replace C109-1 and 9,9'(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole), and the appropriate material ratio was selected. The other raw materials and steps were the same as those in step 2 of synthetic example 7 to obtain the target compound C157.

[0251] Product MS (m / e): 822. 1 H NMR (400MHz, CDCl3): δ8.68(d,2H),8.45-8.36(m,8H),7.90(d,2H),7.83(dd, 2H),7.62(dd,2H),7.53-7.42(m,14H),7.29-7.23(m,4H),3.14-2.95(m,4H).

[0252] Synthesis Example 10: Synthesis of Compound C164

[0253]

[0254] The synthetic route is as follows:

[0255]

[0256] Specific synthesis steps:

[0257] (1) M6 was used instead of M1, and a suitable material ratio was selected. The other raw materials and steps were the same as those in step 1 of Synthesis Example 2 to obtain intermediate C164-1;

[0258] (2) C164-1 was used instead of C109-1, 2-chloro-4,6-diphenyl-1,3,5-triazine was used instead of 9,9'(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole), and the appropriate material ratio was selected. The other raw materials and steps were the same as those in step 2 of Synthesis Example 7 to obtain the intermediate C164-2.

[0259] (3) C164-2 and D8 were used to replace M1 and D3 respectively, and the appropriate material ratio was selected. The other raw materials and steps were the same as those in Synthesis Example 1 to obtain the target compound C164.

[0260] Product MS (m / e): 764. 1 H NMR (400MHz, CDCl3): δ8.66(d,1H),8.45-8.36(m,4H),7.91-7.79(m,3H),7 .72-7.68(d,1H),7.63-7.39(m,13H),7.31-7.23(m,2H),3.13-2.94(m,4H).

[0261] Synthesis Example 11: Synthesis of Compound C195

[0262]

[0263] The synthetic route is as follows:

[0264]

[0265] Specific synthesis steps:

[0266] M7 and D21 were used to replace M1 and D3 respectively, and the appropriate material ratio was selected. Other raw materials and steps were the same as those in Synthesis Example 1 to obtain the target compound C195.

[0267] Product MS (m / e): 870. 1 H NMR (400MHz, CDCl3): δ8.14-8.09(m,1H),7.91(d,1H),7.81(dd,2H),7.70 -7.56(m,11H),7.52-7.39(m,9H),7.38-7.22(m,15),7.16 -7.10(m,2H),7.0(dd,1H).

[0268] Synthesis Example 12: Synthesis of Compound C243

[0269]

[0270] The synthetic route is as follows:

[0271]

[0272] Specific synthesis steps:

[0273] M8 and D8 were used to replace M1 and D3 respectively, and the appropriate material ratio was selected. Other raw materials and steps were the same as those in Synthesis Example 1 to obtain the target compound C243.

[0274] Product MS (m / e): 704; 1 H NMR (400MHz, CDCl3): δ8.15(d,2H),7.74(dd,2H),7.62(dd,2H),7.55(d,2H),7.50(ddd,2H),7.44(dd,2H),7.28(ddd,2H),7.20(s,2H).

[0275] Synthesis Example 13: Synthesis of Compound C253

[0276]

[0277] The synthetic route is as follows:

[0278]

[0279] Specific synthesis steps:

[0280] M9 was used to replace M6, and a suitable material ratio was selected. Other raw materials and steps were the same as those in Synthesis Example 10 to obtain the target compound C253; product MS (m / e): 762.

[0281] Synthesis Example 14: Synthesis of Compound C256

[0282]

[0283] The synthetic route is as follows:

[0284]

[0285] Specific synthesis steps:

[0286] (1) Referring to step (2) of Synthesis Example 7, 2.05 equivalents of 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole were reacted with 1 equivalent of 2,4,6-trichloro-1,3,5-triazine to obtain intermediate C256-1 in a yield of 55%;

[0287] (2) C256-1 was used to replace 9,9'(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole), and the other raw materials and steps were the same as those in Synthesis Example 7 to obtain the target compound C256.

[0288] Product MS (m / e): 921; 1 H NMR (400MHz, CDCl3): δ8.18-8.10(m,8H),8.03(d,1H),7.81(dd,2H),7.68-7.56(m,12H),7.50-7.39(m,6H),7.36-7.23(m,10H),3.16-2.96(m,4H).

[0289] 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 invention by improving it.

[0290] Device Example 1

[0291] 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 by thermal vacuum deposition at a rate of 1.5 %. At the same time, the compound HT and NDP-9 (weight ratio 97:3) were used as the 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, the compound C3 in Synthesis Example 1 was used as a blue light host and BD was used as a dopant (weight ratio 98:2), and 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.

[0292] Device Example 2 to Device Example 14

[0293] The method is the same as that of device embodiment 1, except that compounds C15, C26, C35, C66, C96, C109, C151, C157, C164, C195, C243, C253 and C256 synthesized in synthesis embodiments 2 to 13 in Table 1 are used instead of compound C3 as the blue light host material in the light-emitting layer (EML).

[0294] Device Comparison Example 1

[0295] The method is the same as that of device embodiment 1, except that compound A is used instead of compound C3 as the blue light host material in the light emitting layer (EML).

[0296] The material structure used in the device is shown below:

[0297]

[0298] 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 14 were converted relative to the corresponding data of Comparative Example 1. The relevant data and conversion results are shown in Table 1.

[0299] Table 1

[0300] Device ID Main material Voltage (V) EQE(%) Lifespan (h) Example 1 C3 85％ 115％ 116％ Example 2 C15 86％ 121％ 122％ Example 3 C26 83％ 119％ 120％ Example 4 C35 84％ 120％ 120％ Example 5 C66 88％ 118％ 118％ Example 6 C96 88％ 116％ 116％ Example 7 C109 81％ 126％ 122％ Example 8 C151 82％ 131％ 123％ Example 9 C157 90％ 114％ 116％ Example 10 C164 95％ 102％ 103％ Embodiment 11 C195 92％ 109％ 112％ Example 12 C243 94％ 103％ 105％ Example 13 C253 96％ 101％ 104％ Embodiment 14 C256 84％ 135％ 123％ Comparative Example 1 Compound A 100％ 100％ 100％

[0301] As shown in Table 1, at 10 mA / cm 2 Under the current density, the voltage of device embodiments 1 to device embodiments 14 can be reduced by 4 to 19% relative to comparative example 1, the external quantum efficiency is increased by 1% to 35%, and the device life is extended by 3% to 23%.

[0302] The above data show that the compound with a silicon-containing seven-membered spiro ring structure synthesized by the present invention has a lower driving voltage and higher current efficiency and life in device performance compared with the comparative example compound A due to the introduction of a seven-membered cyclic silicon atom in the structure. This structural change brings about excellent device effects and unexpectedly proves the unique advantages of the compounds of the present invention.

[0303] It should be understood that the various embodiments described herein are only examples and are not intended to limit the scope of the present invention. Therefore, as will be apparent to those skilled in the art, the claimed invention 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 present invention. It should be understood that the various theories about why the present invention works are not intended to be restrictive.

Claims

1. The heterocyclic compound represented by formula I: in, L A , L B , L C and L D Each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof; R A , R B , R C and R D Each is independently selected from a substituted or unsubstituted monocyclic nitrogen-containing heteroaryl group having 3 to 18 carbon atoms, and a substituted or unsubstituted polycyclic nitrogen-containing heteroaryl group having 6 to 30 carbon atoms; n1, n2, n3 and n4 are each independently 0, 1, 2, 3 or 4, and n1, n2, n3 and n4 are not 0 at the same time; represents a single bond or a double bond; When L A , L B , L C , L D , R A , R B , R C and R D When there is a substituent, the substituent is one or more and each is independently selected from deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted deuterated alkyl having 1 to 20 carbon atoms, substituted or unsubstituted haloalkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted deuterated cycloalkyl having 3 to 20 carbon atoms, substituted or unsubstituted halocycloalkyl 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, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, 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 combinations thereof.

2. The compound according to claim 1, characterized in that L A , L B , L C and L D Each is independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms, or a combination thereof; Preferably, L A , L B , L C and L D Each is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazolylene group, or a combination thereof; When L A , L B , L C and L D When there is a substituent, the substituent is one or more and each is independently selected from deuterium, halogen, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a deuterated cycloalkyl group having 3 to 10 carbon atoms, a halocycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkylsilyl group having 3 to 10 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, and a combination thereof; Preferably, L A , L B , L C and L D Each is independently selected from a single bond, a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the group consisting of the following structures: Wherein, when the group W contains a substituent, the substituent is one or more and each is independently selected from deuterium, halogen, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkylsilyl group having 3 to 10 carbon atoms, and an arylsilyl group having 6 to 20 carbon atoms; preferably deuterium, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, trimethylsilyl and triphenylsilyl; represents the position of connection to the benzene ring of the compound of formula I, Represents R A , R B , R C or R D The location of the connection.

3. The compound according to claim 1 or 2, characterized in that L A , L B , L C and L D Each is independently selected from the group consisting of a single bond or the following groups: Preferably, L A , L B , L C and L D Each is independently selected from the group consisting of a single bond or the following groups: represents the position of connection to the benzene ring of the compound of formula I, Represents R A , R B , R C or R D The location of the connection.

4. The compound according to any one of claims 1 to 3, characterized in that R A , R B , R C and R D Each is independently selected from a substituted or unsubstituted group Z, wherein the unsubstituted group Z is selected from the structures shown in the following formula III-1 to formula III-3; In formula III-1 and formula III-2, X is independently selected from a single bond, O, S, CR1R2 or SiR1R2; in formula III-3, X1, X2, X3 are each independently selected from CH and N, and at least one of X1, X2 and X3 is N; R1 and R2 are each independently selected from hydrogen, deuterium, halogen, alkyl having 1-20 carbon atoms, deuterated alkyl having 1-20 carbon atoms, haloalkyl having 1-20 carbon atoms, cycloalkyl having 3-20 carbon atoms, deuterated cycloalkyl having 3-20 carbon atoms, halocycloalkyl having 3-20 carbon atoms, heteroalkyl having 1-20 carbon atoms, heterocycloalkyl having 3-20 carbon atoms, arylalkyl having 7-30 carbon atoms, arylalkyl having 1-20 carbon atoms, atom, an alkoxy group having 6-30 carbon atoms, an aryl group having 6-30 carbon atoms, an aryloxy group having 6-30 carbon atoms, a heteroaryl group having 3-30 carbon atoms, an alkenyl group having 2-20 carbon atoms, an alkynyl group having 2-20 carbon atoms, an alkylsilyl group having 3-20 carbon atoms, an arylsilyl group having 6-20 carbon atoms, an amino group having 0-20 carbon atoms, 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 combinations thereof; Preferably, R1 and R2 are each independently selected from hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a deuterated cycloalkyl group having 3 to 10 carbon atoms, a halocycloalkyl group having 3 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, and combinations thereof; When the group Z contains a substituent, the substituent is one or more and each is independently selected from deuterium, halogen, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a deuterated cycloalkyl group having 3 to 10 carbon atoms, a halocycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkylsilyl group having 3 to 10 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, and a combination thereof.

5. The compound according to claim 4, characterized in that The unsubstituted group Z is selected from the group consisting of the structures shown in the following formula: Indicates that L A , L B , L C or L D The location of the connection; Preferably, when the group Z contains a substituent, the substituent is one or more and each is independently selected from deuterium, halogen, an alkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkylsilyl group having 3 to 10 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, and combinations thereof; preferably deuterium, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, biphenyl, naphthyl, anthracenyl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, trimethylsilyl, triphenylsilyl, N-phenylcarbazolyl, and combinations thereof; Preferably, R A , R B , R C and R D Each is independently selected from the group consisting of the following structures:

6. The compound according to any one of claims 1 to 5, characterized in that The compounds have structures shown in the following formulas I-1 to I-8: Among them, L A , L B , L C , L D , R A , R B , R C and R D The definition is the same as that in any one of claims 1 to 5, and n1, n2, n3 and n4 are each independently 1 or 2; Preferably, Each is independently selected from the group consisting of:

7. The compound according to any one of claims 1 to 6, characterized in that The compound is selected from the group consisting of the following structures:

8. Use of the compound according to any one of claims 1 to 7 in the preparation of an organic electroluminescent device; Preferably, the compound is used as a host material of a light-emitting layer in an organic electroluminescent device, and more preferably as a blue light-emitting host material of the light-emitting layer.

9. An organic electroluminescent device, comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, wherein the main material of the light-emitting layer contains the compound according to any one of claims 1 to 7; Preferably, the organic electroluminescent device further comprises one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer and an electron injection layer.

10. A display component / device comprising the organic electroluminescent device according to claim 9.

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