Heterocyclic compound and use thereof

Abstract

Provided in the present invention are a heterocyclic compound and the use thereof. The heterocyclic compound of the present invention has a structure represented by formula I, and can be used as a blue-light-emitting material of an organic electroluminescent device to improve the light-emitting performance of the device.

Description

A heterocyclic compound and its application

[0001] Cross-references to related applications

[0002] This application claims priority to Chinese Patent Application No. 202410947427.6, filed on July 15, 2024, the entire contents of which are incorporated herein by reference. Technical Field

[0003] This invention belongs to the field of organic electroluminescence technology, specifically relating to a heterocyclic compound and its application in organic electroluminescent devices. Background Technology

[0004] Organic electroluminescent displays are hailed as the "third display technology revolution" due to their numerous advantages, including self-illumination, wide viewing angle, high contrast, fast response, low power consumption, thinner and lighter design, and the ability to achieve flexible displays. They are widely used in mobile phones, televisions, computers, automotive displays, and other display and lighting applications.

[0005] With the development of organic electroluminescent materials, red and green light-emitting materials have largely met the needs of displays. However, blue light-emitting materials, due to their wide bandgap characteristics and difficulty in charge injection, lag behind red and green light in terms of efficiency and lifetime. Nevertheless, the performance of blue light emission, especially deep blue light, has a significant impact on improving display quality and reducing power consumption.

[0006] Commercially viable blue light-emitting materials require high efficiency and long lifespan. Chinese patent application CN103222082A discloses an aromatic vinyl compound for use as a blue electroluminescent material; however, this compound has poor heat resistance and is prone to decomposition during sublimation. Similarly, Chinese patent application CN1394195A discloses a series of anthracene derivatives that can be used as blue light materials for OLEDs, but these anthracene derivatives have low efficiency and cannot meet the requirements of current displays in practical applications. Furthermore, Chinese patent application CN101018760A discloses a series of aromatic amine derivatives, but due to the imbalance between their hole and electron transport properties, their lifespan remains unsatisfactory.

[0007] Developing high-efficiency and long-life blue luminescent materials is of great significance for promoting the development of organic electroluminescent display and lighting technologies. Current technologies still require improvement and further development.

[0008] Summary of the Invention

[0009] In view of the various defects and shortcomings of the existing technology, the purpose of this invention is to provide a heterocyclic compound and its application. The heterocyclic compound of this invention can be used as a blue host material for organic electroluminescence, thereby improving the luminescence performance of organic electroluminescent devices.

[0010] In a first aspect, the present invention provides a heterocyclic compound having the structure shown in Formula I:

[0011] Among them, L A L B L C and L D Each is independently selected from single-bonded, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, or combinations thereof;

[0012] R A R B R C and R D Each is independently selected from substituted or unsubstituted monocyclic nitrogen-containing heteroaryl groups having 3-18 carbon atoms, or substituted or unsubstituted polycyclic nitrogen-containing heteroaryl groups having 6-30 carbon atoms;

[0013] n1, n2, n3 and n4 are each independently 0, 1, 2, 3 or 4, and n1, n2, n3 and n4 are not all 0 at the same time;

[0014] Represents a single bond or a double bond;

[0015] When L A L B L C L D R A R B R C and R DWhen substituents are present, the substituents are one or more, each independently selected from deuterium, halogens, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted deuterated alkyl groups having 1-20 carbon atoms, substituted or unsubstituted haloalkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted deuterated cycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted halocycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-20 carbon atoms, and substituted or unsubstituted groups having 7-30 carbon atoms. Aryl groups having 1-20 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, alkoxysilyl groups having 3-20 carbon atoms, arylsilyl groups having 6-20 carbon atoms, and amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms.

[0016] In this invention, n1 represents the relationship with L A Connected R A The number of elements, n2 represents the number of elements in relation to L. B Connected R B The number of elements, n3 represents the number of elements in relation to L. C Connected R C The number of elements, n4 represents the number of elements with respect to L. D Connected R D The number of.

[0017] In this invention, the structure shown in Formula I can be represented as the structure shown in Formula 1 or Formula 2:

[0018] In Equations 1 and 2, the symbols are defined the same as in Equation 1.

[0019] According to some embodiments of the present invention, L A To L D Each is independently selected from single-bonded, substituted or unsubstituted aryl groups having 6-20 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-20 carbon atoms, or combinations thereof.

[0020] According to some embodiments of the present invention, L A L B L C and L DEach is independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted carbazolyl group, or a combination thereof.

[0021] According to some embodiments of the present invention, when L A L B L C and L D When substituents are present, the substituents are one or more, and each is independently selected from deuterium, halogens, alkyl groups having 1-10 carbon atoms, deuterated alkyl groups having 1-10 carbon atoms, haloalkyl groups having 1-10 carbon atoms, cycloalkyl groups having 3-10 carbon atoms, deuterated cycloalkyl groups having 3-10 carbon atoms, halocycloalkyl groups having 3-10 carbon atoms, aryl groups having 6-18 carbon atoms, heteroaryl groups having 3-18 carbon atoms, alkoxyl groups having 3-10 carbon atoms, arylsilyl groups having 6-20 carbon atoms, and combinations thereof.

[0022] According to some embodiments of the present invention, L A L B L C and L D Each group W is independently selected from single-bonded, substituted, or unsubstituted groups, wherein the unsubstituted groups W are selected from the group consisting of the following structures:

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

[0024] Indicates the position where it is attached to the benzene ring of the compound of formula I. Indicates with 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] Indicates the position where it is attached to the benzene ring of the compound of formula I. Indicates with R A R B R C Or R D The location of the connection.

[0027] 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:

[0028] Indicates the position where it is attached to the benzene ring of the compound of formula I. Indicates with 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 single bonds, phenylene, deuterated phenylene, carbazolyl, benzene-substituted carbazolyl, and combinations thereof. In some embodiments, L A L B L C and L D All are single bonds. In some implementations, L B It is phenylene, deuterated phenylene, or carbazolyl, L A L C and L D All are single keys.

[0030] According to some embodiments of the present invention, R A R B R C and R D Each is independently selected from substituted or unsubstituted monocyclic nitrogen-containing heteroaryl groups having 3-18 carbon atoms, or substituted or unsubstituted polycyclic nitrogen-containing heteroaryl groups having 12-30 carbon atoms.

[0031] In this invention, R A R B R C and R DThe number of nitrogen atoms in the monocyclic nitrogen-containing heteroaryl and polycyclic nitrogen-containing heteroaryl involved is 1 to 4, preferably 1 to 3. The monocyclic nitrogen-containing heteroaryl and polycyclic nitrogen-containing heteroaryl may also contain 1 to 4 other heteroatoms, such as O, S, Se, Si, etc.

[0032] According to some embodiments of the present invention, R A R B R C and R D Each group Z is independently selected from substituted or unsubstituted groups, wherein the unsubstituted groups Z are selected from the structures shown in Formula III-1 to Formula III-3 below;

[0033] In Formula III-1 and Formula III-2, X is independently selected from single bond, O, S, CR1R2 or SiR1R2; in Formula III-3, X1, X2 and X3 are each independently selected from CH and N, and at least one of X1, X2 and X3 is N;

[0034] R1 and R2 are each independently selected from hydrogen, deuterium, halogen, alkyl groups having 1-20 carbon atoms, deuterated alkyl groups having 1-20 carbon atoms, haloalkyl groups having 1-20 carbon atoms, cycloalkyl groups having 3-20 carbon atoms, deuterated cycloalkyl groups having 3-20 carbon atoms, halocycloalkyl groups having 3-20 carbon atoms, heteroalkyl groups having 1-20 carbon atoms, heterocycloalkyl groups having 3-20 carbon atoms, aralkyl groups having 7-30 carbon atoms, and alkyl groups having 1-20 carbon atoms. Alkyl groups having 6-30 carbon atoms, aryl groups having 6-30 carbon atoms, heteroaryl groups having 3-30 carbon atoms, alkenyl groups having 2-20 carbon atoms, alkynyl groups having 2-20 carbon atoms, alkylsilyl groups having 3-20 carbon atoms, arylsilyl groups having 6-20 carbon atoms, amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms;

[0035] When group Z contains a substituent, the substituent is one or more, and each is independently selected from deuterium, halogen, alkyl having 1-10 carbon atoms, deuterated alkyl having 1-10 carbon atoms, haloalkyl having 1-10 carbon atoms, cycloalkyl having 3-10 carbon atoms, deuterated cycloalkyl having 3-10 carbon atoms, halocycloalkyl having 3-10 carbon atoms, aryl having 6-18 carbon atoms, heteroaryl having 3-18 carbon atoms, alkoxysilyl having 3-10 carbon atoms, arylsilyl having 6-20 carbon atoms, and combinations thereof.

[0036] According to some embodiments of the present invention, R1 and R2 are each independently selected from hydrogen, deuterium, alkyl groups having 1-10 carbon atoms, deuterated alkyl groups having 1-10 carbon atoms, haloalkyl groups having 1-10 carbon atoms, cycloalkyl groups having 3-10 carbon atoms, deuterated cycloalkyl groups having 3-10 carbon atoms, halocycloalkyl groups having 3-10 carbon atoms, aralkyl groups having 7-20 carbon atoms, aryl groups having 6-20 carbon atoms, and combinations thereof.

[0037] According to some embodiments of the present invention, R1 and R2 are each independently selected from hydrogen, deuterium, alkyl groups having 1-6 carbon atoms, deuterated alkyl groups having 1-6 carbon atoms, haloalkyl groups having 1-6 carbon atoms, aryl groups having 6-15 carbon atoms, and combinations thereof.

[0038] 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.

[0039] According to some embodiments of the present invention, the unsubstituted group Z is selected from the group consisting of structures represented by the following formulas:

[0040] Indicates with L A L B L C or L D The location of the connection.

[0041] In this invention, when group Z contains a substituent, the substituent is one or more, and each is independently selected from deuterium, halogen, alkyl group having 1-10 carbon atoms, deuterated alkyl group having 1-10 carbon atoms, haloalkyl group having 1-10 carbon atoms, aryl group having 6-18 carbon atoms, heteroaryl group having 3-18 carbon atoms, alkoxyl group having 3-10 carbon atoms, arylsilyl group having 6-20 carbon atoms, and combinations thereof; for example, each substituent is independently selected from deuterium, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, biphenyl, naphthyl, anthracene, phenanthrene, dibenzofuranyl, dibenzothiophene, carbazole, fluorenyl, trimethylsilyl, triphenylsilyl, N-phenylcarbazole, and combinations thereof.

[0042] 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:

[0043] According to some embodiments of the present invention, the compound has the structure shown in Formulas I-1 to I-8:

[0044] In equations I-1 to I-8, L A L B L C L D R A R B R C and R D The definitions are the same as those mentioned above in this article, with n1, n2, n3, and n4 each being 1 or 2 independently.

[0045] According to some embodiments of the present invention, the compound has a structure represented by formulas 1-1 to 1-8 and 2-1 to 2-8:

[0046] In equations 1-1 to 1-8 and equations 2-1 to 2-8, L A L B L C L D R A R B R C R D The definitions of n1, n2, n3 and n4 are the same as those in the previous definition in this article.

[0047] 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 equations 3-1 to 3-12 below:

[0048] In Equations 3-1 to 3-12, X is selected from single bond, O, S, CR1R2 or SiR1R2; Z1 and Z2 represent mono- or poly-substituted substances;

[0049] Z1, Z2, R1, and R2 are each independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1-20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted heteroalkyl groups having 1-20 carbon atoms, substituted or unsubstituted heterocycloalkyl groups having 3-20 carbon atoms, substituted or unsubstituted aralkyl groups having 7-30 carbon atoms, substituted or unsubstituted alkoxy groups having 1-20 carbon atoms, substituted or unsubstituted aryl groups having 6-30 carbon atoms, substituted or unsubstituted aryloxy groups having 6-30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3-30 carbon atoms, substituted or Unsubstituted alkenyl groups having 2-20 carbon atoms, substituted or unsubstituted alkynyl groups having 2-20 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3-20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6-20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphinyl, and combinations thereof having 0-20 carbon atoms; wherein the substituent used for substitution is selected from deuterium, halogen, alkyl groups having 1-10 carbon atoms, cycloalkyl groups having 3-10 carbon atoms, aryl groups having 6-20 carbon atoms, or heteroaryl groups having 3-20 carbon atoms.

[0050] According to some preferred embodiments of the present invention, in formulas 3-1 to 3-12, X is selected from single bonds or SiR1R2.

[0051] According to some embodiments of the present invention, in formulas 3-1 to 3-12, Ar1 and Ar2 are each independently selected from hydrogen, the structure shown in formula 4 or formula 5:

[0052] In Equations 4 and 5, the definition of X is the same as that in Equations 3-1 to 3-12;

[0053] Z1 to Z3 represent mono- or poly-substituted substances. The definitions of Z1 to Z3 are the same as those of Z1 and Z2 in Equations 3-1 to 3-12.

[0054] According to some preferred embodiments of the present invention, L A To L D It is independently selected from single bonds, phenylene, deuterated phenylene, pyridyl, pyrimidinyl, triazine, carbazolyl, and combinations thereof.

[0055] In some preferred embodiments, Each is independently selected from the group consisting of the following structures:

[0056] In some preferred embodiments, Each is independently selected from the group consisting of the following structures:

[0057] In some preferred embodiments, the compound is selected from compounds numbered C1 to C255:

[0058] Secondly, the present invention provides the application of the above-mentioned compounds in the preparation of organic electroluminescent devices.

[0059] According to some embodiments of the present invention, the compound is used as the host material of the light-emitting layer in an organic electroluminescent device.

[0060] According to some preferred embodiments of the present invention, the compound is used as a blue light host material for the light-emitting layer in an organic electroluminescent device.

[0061] Thirdly, 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 compound described above in the present invention.

[0062] 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).

[0063] According to some preferred embodiments of the present invention, the organic electroluminescent device further includes one or more of the following: 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.

[0064] Fourthly, the present invention provides a display component / device comprising 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. Attached Figure Description

[0065] Figure 1 is a schematic diagram of an organic light-emitting device according to a specific embodiment of the present invention.

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

[0067] The reference numerals in the attached figures are as follows: 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 Implementation

[0068] The technical solution of the present invention will be described in detail below through specific embodiments. The following embodiments are used to illustrate the present invention, but are not intended to limit the scope of the present invention. All equivalent changes or modifications made without departing from the spirit disclosed in the present invention should be included within the scope of the claims.

[0069] OLEDs can be fabricated on various substrates, such as glass, plastic, and metal. Figure 1 schematically and non-limitingly illustrates a first organic light-emitting device 100. The figure is not necessarily drawn to scale, and some layer structures may be omitted as needed. 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. Device 100 can be fabricated by sequentially depositing the described layers. The properties and functions of each layer, as well as 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.

[0070] Each of these layers has numerous examples. For instance, a flexible and transparent substrate-anode combination is disclosed in U.S. Patent No. 5,844,363, which is incorporated herein 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 herein 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 herein 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 herein by reference in its entirety. Examples of cathodes are disclosed in U.S. Patent Nos. 5,703,436 and 5,707,745, which are incorporated herein by reference in their entirety. These cathodes comprise composite cathodes having a thin metal layer, such as Mg:Ag, overlaid with a 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 also incorporated herein by reference in their entirety. Examples of implantation layers are provided in U.S. Patent Application Publication No. 2004 / 0174H6, which is incorporated herein 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 herein by reference in its entirety.

[0071] The layered structure described above is provided through non-limiting embodiments. The functionality of an OLED can be achieved by combining the various layers described above, or some layers can be omitted entirely. It may 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 may include several sublayers. For example, a light-emitting layer may have two different light-emitting materials to achieve a desired emission spectrum.

[0072] In one embodiment, an OLED can be described as having an "organic layer" disposed between a cathode and an anode. This organic layer may include one or more layers.

[0073] OLEDs also require an encapsulation layer. Figure 2 schematically and non-limitingly illustrates a second organic light-emitting device 200, which, unlike Figure 1, may include an encapsulation layer 102 above the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing encapsulation can be used as the 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. Patent 7,968,146B2, the entire contents of which are incorporated herein by reference.

[0074] Devices manufactured according to embodiments of the present invention can be incorporated into a variety of consumer products having one or more electronic component modules (or units). Some examples of such 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, smartphones, tablet computers, phablets, wearable devices, smartwatches, laptop computers, digital cameras, portable camcorders, viewfinders, microdisplays, 3D displays, vehicle displays, and taillights.

[0075] The materials and structures described in this article can also be used in other organic electronic devices listed above.

[0076] Definition of the term "substituent group"

[0077] The term “halogen or halide” as used in this article includes fluorine, chlorine, bromine, and iodine.

[0078] As used herein, the term "alkyl" includes both straight-chain and branched alkyl groups. An 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, isolaryl, 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-pentadecanyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, and 3-methylpentyl. Furthermore, the alkyl group may optionally be substituted. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, neopentyl, and n-hexyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0079] As used herein, the term "alkenyl" includes a straight-chain, branched, or cyclic non-aromatic hydrocarbon group with one or more carbon-carbon double bonds. An alkenyl group can be a straight-chain, branched, or cyclic non-aromatic hydrocarbon group with 2-20 carbon atoms and having one or more carbon-carbon double bonds, preferably an alkenyl group with 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-hextrienyl, etc. Furthermore, the alkenyl group may optionally be substituted.

[0080] As used herein, the term "cycloalkyl" includes cyclic alkyl groups. A cycloalkyl group can be a cycloalkyl group having 3 to 20 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, and 4,4-dimethylcyclohexyl are preferred. Furthermore, the cycloalkyl group may optionally be substituted.

[0081] As used herein, the term "heteroalkyl" refers to an alkyl chain in which one or more carbon atoms are substituted with heteroatoms selected from the group consisting of nitrogen, oxygen, sulfur, selenium, phosphorus, silicon, germanium, and boron atoms. Heteroalkyl groups can be of 1 to 20 carbon atoms, preferably of 1 to 10 carbon atoms, and more preferably of 1 to 6 carbon atoms. Examples of heteroalkyl groups include methoxymethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, ethylthioethyl, methoxymethoxymethyl, ethoxymethoxymethyl, ethoxyethoxyethyl, hydroxymethyl, hydroxyethyl, hydroxypropyl, mercaptomethyl, mercaptoethyl, mercaptopropyl, aminomethyl, aminoethyl, aminolactone, dimethylaminomethyl, trimethylsilyl, dimethylethylsilyl, dimethylisolactone, tert-butyldimethylsilyl, triethylsilyl, triisolactone, trimethylsilylmethyl, trimethylsilylethyl, and trimethylsilylisolactone. In addition, heteroalkyl groups may be optionally substituted.

[0082] The terms "heterocyclic alkyl" and "heterocyclic group," "heterocycle," "carbon heterocyclic," and "carbon heterocyclic group" as used herein are used interchangeably and include both aromatic and non-aromatic cyclic groups. Aromatic cyclic groups include heteroaromatic groups having 3-18 ring atoms, wherein at least one ring atom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. 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, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Preferred non-aromatic heterocyclic groups are those having 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen, silicon, or sulfur. Non-aromatic heterocyclic groups include ethylene oxide, oxetane, tetrahydrofuranyl, tetrahydropyranyl, dioxopentacycloyl, dioxahexacycloyl, acridineyl, dihydropyrroleyl, tetrahydropyrroleyl, piperidinyl, oxazolyl, morpholinyl, piperazineyl, oxetane-heptanetrienyl, thioheptanetrienyl, azirane-heptanetrienyl, and tetrahydrothiopyrroleyl. Furthermore, the heterocyclic group may optionally be substituted.

[0083] The term "aryl or aromatic group" as used herein includes both non-fused and fused systems. The aryl group can 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, fenene, fluorene, pyrene, etc. Perylene and azulene, preferably phenyl, biphenyl, triphenylene, fluorene, and naphthalene. Additionally, the aryl group may optionally be substituted. Examples of non-fused aryl groups 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'-methyldiphenyl, 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-tetraphenyl. Additionally, the aryl group may optionally be substituted.

[0084] In this application, "arylene" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from an aryl group. When the number of other groups attached to a given arylene group is 0 (non-existent), the arylene group is considered an aryl group. For example, in Formula I, when L... A It is a aryl group, and is related to L A The attached group R A When the number of elements n1 = 0, L A It is considered an aryl group.

[0085] As used herein, the term "heteroaryl" includes non-fused and fused heteroaryl groups with 1 to 5 heteroatoms, wherein at least one heteroatom is selected from the group consisting of nitrogen, oxygen, sulfur, selenium, silicon, phosphorus, germanium, and boron. Isoaryl also refers to heteroaryl. Heteroaryl can 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, oxtriazole, dioxazole, thiadiazol, pyridine, pyrazine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indole, benzimidazole, indazole, indoxazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, iso Quinoline, cyclophosphine, quinazolin, quinoxaline, naphthidine, phthalazine, pteridine, guarbenzine, acridine, phenazine, phenothiazine, benzofuranopyridine, furanodipyridine, benzothiophenopyridine, thiophenodipyridine, benzoselenophenopyridine, selenobenzodipyridine, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1,2-azaborane, 1,3-azaborane, 1,4-azaborane, boronazole and its aza analogues. Additionally, the heteroaryl group may optionally be substituted.

[0086] In this application, "heteroaryl" refers to a divalent or polyvalent group formed by the further loss of one or more hydrogen atoms from a "heteroaryl" group. When the number of other groups attached to a certain heteroaryl group is 0 (non-existent), the heteroaryl group is considered a heteroaryl. For example, in Formula I, when L... A It is a heteroaryl group, and it is related to L. A The attached group R A When the number of elements n1 = 0, L A It is considered a heteroaryl group.

[0087] As used herein, the term "alkoxy" is represented by -O-alkyl, -O-cycloalkyl, -O-heteroalkyl, or -O-heterocyclic. Examples and preferred examples of alkyl, cycloalkyl, heteroalkyl, and heterocyclic groups are the same as described above. An alkoxy group can be an alkoxy group having 1 to 20 carbon atoms, preferably an alkoxy group having 1 to 6 carbon atoms. Examples of alkoxy groups include methoxy, ethoxy, propoxy, butoxy, pentoxy, hexoxy, cyclopropyloxy, cyclobutyloxy, cyclopentoxy, cyclohexyloxy, tetrahydrofuranyloxy, tetrahydropyranyloxy, methoxypropyloxy, ethoxyethyloxy, methoxymethyloxy, and ethoxymethyloxy. Additionally, the alkoxy group may optionally be substituted.

[0088] As used herein, the term "aryloxy group" is denoteed by -O-aryl or -O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. An aryloxy group can be an aryloxy group having 6 to 30 carbon atoms, preferably an aryloxy group having 6 to 20 carbon atoms. Examples of aryloxy groups include phenoxy and biphenyloxy groups. Additionally, aryloxy groups may optionally be substituted.

[0089] As used herein, the term "aralkyl" encompasses aryl-substituted alkyl groups. Aralkyl groups can be aralkyl groups having 7 to 30 carbon atoms, preferably aralkyl groups having 7 to 20 carbon atoms, and more preferably aralkyl groups 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 The compounds include alkyl groups, such as o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-hydroxy-2-phenylisopropyl, and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, and 2-phenylisopropyl are preferred. Additionally, the alkyl group may optionally be substituted.

[0090] As used herein, the term "alkylsilyl or silyl" encompasses silyl groups substituted with groups listed in the above alkyl groups, such as methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl, etc.

[0091] As used herein, the term "arylsilyl" refers to a group consisting of any of the aforementioned aryl and silyl groups, such as triphenylsilyl.

[0092] As used herein, the term "aza" in terms such as "azadibenzofuran" and "azadibenzothiophene" refers to a cyclic aromatic segment in which one or more CH groups are replaced by nitrogen atoms. For example, azatriphenylene includes dibenzo[f,h]quinoline, dibenzo[f,h]quinoline, and other analogs having two or more nitrogen atoms in the ring system. Other nitrogen analogs of the aforementioned aza derivatives will readily conceive of those skilled in the art, and all such analogs are identified as being included in the terminology used herein.

[0093] In this disclosure, unless otherwise defined, when any of the terms consisting of the group consisting of, for example, substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted heterocyclic, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted alkynyl, substituted aryl, substituted heteroaryl, substituted alksilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphinyl, refers to any one of the following groups: alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alksilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl, and phosphinyl, which may be one or more groups selected from deuterium, halogen, unsubstituted alkyl having 1-20 carbon atoms, and unsubstituted... The substituted cycloalkyl group having 3-20 carbon atoms, the unsubstituted heteroalkyl group having 1-20 carbon atoms, the unsubstituted heterocyclic group having 3-20 carbon atoms, the unsubstituted aralkyl group having 7-30 carbon atoms, the unsubstituted alkoxy group having 1-20 carbon atoms, the unsubstituted aryl group having 6-30 carbon atoms, the unsubstituted alkenyl group having 2-20 carbon atoms, the unsubstituted alkynyl group having 2-20 carbon atoms, the unsubstituted aryl group having 6-30 carbon atoms, the unsubstituted heteroaryl group having 3-30 carbon atoms, the unsubstituted alksilyl group having 3-20 carbon atoms, the unsubstituted arylsilyl group having 6-20 carbon atoms, and the unsubstituted amino, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxyl, mercapto, sulfinyl, sulfonyl, phosphin, and combinations thereof having 0-20 carbon atoms.

[0094] It should be understood that when a molecular segment is described as a substituent or otherwise attached to another part, its name may be written according to whether it is a segment (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 substituents or attaching segments are considered equivalent.

[0095] In the compounds mentioned in this 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. Substitution with other stable isotopes in the compounds is likely preferred due to their ability to enhance device efficiency and stability.

[0096] In the compounds mentioned in this disclosure, multiple substitution refers to the range including disubstitution, up to the maximum number of available substitutions. When a substituent in a compound mentioned in this disclosure represents multiple substitution (including disubstitution, trisubstitution, tetrasubstitution, etc.), it means that the substituent can be present at multiple available substitution positions on its linkage structure. The substituent present at multiple available substitution positions can be the same structure or different structures.

[0097] In the compounds mentioned in this disclosure, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compounds cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the resulting ring can be a monocyclic or polycyclic ring, and can be an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. In this context, 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.

[0098] The materials described in this invention for specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in the device. These combinations of materials are 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 herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0099] Materials described herein for use in specific layers in organic light-emitting devices can be used in combination with a variety of other materials present in said devices. For example, the compounds disclosed herein can be used in combination with a variety of host layers, delivery layers, barrier layers, injection layers, electrodes, and other possible layers. These combinations of materials are 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 herein are non-limiting examples of materials that can be used in combination with the compounds disclosed herein, and those skilled in the art can readily consult the literature to identify other materials that can be used in combination.

[0100] In the examples of material synthesis, unless otherwise stated, all reactions were carried out under nitrogen protection. All reaction solvents were anhydrous and used as is from commercial sources. The synthesized products were structurally confirmed and characterized using one or more instruments conventional in the art (including but not limited to Agilent liquid chromatographs, liquid chromatography-mass spectrometers, gas chromatography-mass spectrometers, differential scanning calorimeters, fluorescence spectrophotometers, electrochemical workstations, sublimation apparatuses, etc.) in methods well known to those skilled in the art. In the examples of devices, the characteristics of the devices were also tested using conventional instruments in the art (including but not limited to vapor deposition machines manufactured by Nanjing Institute of Microelectronics, optical testing systems and lifetime testing systems manufactured by Suzhou Fushida, ellipsometers manufactured by Wuhan Yiguang Technology, etc.) in methods well known to those skilled in the art. Since those skilled in the art are familiar with the use of the above-mentioned equipment, testing methods, and other related content, and can obtain the inherent data of the samples definitively and unaffected, the above-mentioned related content will not be elaborated further in this patent.

[0101] The preparation methods of the compounds of this invention are not limited. Typical but not limited examples are the following compounds, whose synthetic routes and preparation methods are as follows:

[0102] Intermediate synthesis examples:

[0103] Example 1: Synthesis of intermediate M1

[0104] (1) Under nitrogen protection, 600 mL of tetrahydrofuran and 158.75 g of 2-iodo-4-chlorobromobenzene were added to a 2 L three-necked reaction flask. The mixture was stirred and cooled to -10 °C to -5 °C under nitrogen protection. 275 mL of tetrahydrofuran solution of isopropyl magnesium chloride was added dropwise over about 1 hour. The mixture was kept at 0 °C to -5 °C for 1 hour. The mixture was then cooled to 0 °C to -5 °C and a solution of 114.54 g of methyl 2-acetate bromobenzene and 150 mL of tetrahydrofuran was added dropwise over 1 hour. The mixture was then naturally heated to room temperature and stirred for 8 hours. 100 mL of concentrated hydrochloric acid was added dropwise below 0 °C and stirred for 5 minutes. 500 mL of ethyl acetate was added, and the mixture was allowed to stand and separated. The organic phase was washed until neutral. The solvent was evaporated under vacuum. The residue was dissolved and crystallized in 600 mL of n-heptane. The solution was filtered, dried, and the quantity was 99.1 g, with a yield of 51%. The product was designated as S1.

[0105] (2) Add 1 liter of ethylene glycol monohydrate, 18.55 g of potassium hydroxide, 20.38 g of hydrazine hydrate and 99.1 g of S1 to a 2-liter three-necked reaction flask. Stir and heat to 160°C to 170°C and react for 8 hours. Monitor the reaction by TLC. When the reactants are completely reacted, cool to room temperature and add 100 mL of water and 500 mL of toluene. Let stand and separate the liquids. Wash the organic phase until neutral. Evaporate the solvent under vacuum. Dissolve the residue in 150 mL of toluene to crystallize. Filter and dry. The quantity is 74.5 g, and the yield is 78%. The product is named S2.

[0106] (3) 78.0 g of 2,2'-dibromobiphenyl and 500 mL of tetrahydrofuran were added to a 2 L three-necked flask. Stirring was started, and the temperature was lowered to -70°C to -80°C under nitrogen protection. 100 mL of butyllithium was added dropwise at -70°C to -80°C over approximately 1 hour. The temperature was then maintained at -70°C to -80°C for 1 hour. A solution prepared with 42.5 g of tetrachlorosilane and 50 mL of tetrahydrofuran was added dropwise over approximately 0.5 hours. After the addition was complete, the temperature was allowed to rise naturally to room temperature. The solution was acidified with 50 mL of concentrated hydrochloric acid, and 150 mL of ethyl acetate was added. The mixture was separated, and the organic phase was washed until neutral. The solvent was evaporated under vacuum, and 300 mL of heptane was added. The mixture was stirred for 0.5 hours, cooled to room temperature, and filtered. The yield was 25.7 g after drying, with a yield of 41%. The product was designated as S3.

[0107] (4) Add 18.83 g of S2 and 200 mL of tetrahydrofuran to a 1 L three-necked flask, start stirring, and cool to -70°C to -80°C under nitrogen protection. Add 20 mL of butyllithium dropwise at -70°C to -80°C over approximately 0.5 hours. Maintain the temperature at -70°C to -80°C for 0.5 hours. Add 12.55 g of S3 and a solution prepared with 30 mL of tetrahydrofuran dropwise over approximately 0.5 hours. After the addition is complete, allow the temperature to rise naturally to room temperature. Acidify with 10 mL of concentrated hydrochloric acid, add 100 mL of ethyl acetate, separate the liquid, wash the organic phase until neutral, evaporate the solvent under vacuum, dissolve in 700 mL of heptane, pass through a 10 g silica gel column, concentrate the column chromatography solution to approximately 60 mL under normal pressure, cool to room temperature, and filter. The yield after drying is 9.27 g, yield 47%, and the product is designated as M1.

[0108] 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).

[0109] Example 2: Synthesis of intermediate M2

[0110] Using compounds replace By selecting a suitable material ratio, and keeping other raw materials and steps the same as in Example 1, intermediate M2 was obtained. Product MS (m / e): 394.

[0111] Example 3: Synthesis of intermediate M3

[0112] Using compounds replace By selecting a suitable material ratio, and keeping other raw materials and steps the same as in Example 1, intermediate M3 was obtained. Product MS (m / e): 394.

[0113] Example 4: Synthesis of intermediate M4

[0114] (1) Use raw materials replace Select a suitable material ratio, and keep other raw materials and steps the same as steps 1-2 of Example 1 to obtain S9;

[0115] (2) Add 141.5 g of 2-bromophenyl benzoyl 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 to a 2 L three-necked reaction flask. Purge with nitrogen three times, start stirring, heat to 70 °C to 75 °C, keep the reaction at this temperature for 24 hours, cool to room temperature, add 100 mL of water, let stand and separate the liquids, wash the organic phase until neutral, evaporate the solvent under vacuum, add 900 mL of heptane, pass through a silica gel column, evaporate the solvent under vacuum after passing through the column, add 200 mL of anhydrous ethanol to dissolve and crystallize, filter, dry to obtain 85.5 g of solid, yield 50%, the product is designated as S10;

[0116] (3) Add 85.5 g of S10 and 500 mL of tetrahydrofuran to a 2 L three-necked flask, start stirring, and cool to -70°C to -80°C under nitrogen protection. Add 100 mL of butyllithium dropwise at -70°C to -80°C over approximately 1 hour. Maintain the temperature at -70°C to -80°C for 1 hour. Add a solution prepared with 42.5 g of tetrachlorosilane and 50 mL of tetrahydrofuran over approximately 0.5 hours. After the addition is complete, allow the temperature to rise naturally to room temperature. Acidify with 50 mL of concentrated hydrochloric acid, add 150 mL of ethyl acetate, separate the liquid, wash the organic phase until neutral, evaporate the solvent under vacuum, add 300 mL of heptane, stir for 0.5 hours, cool to room temperature, and filter. The yield was 26 g after drying, with a yield of 37%. The product was designated as S11.

[0117] (4) Add 17.00 g of S9 and 150 mL of tetrahydrofuran to a 0.5 L three-necked flask, start stirring, and cool to -70°C to -80°C under nitrogen protection. Add 22 mL of butyllithium dropwise at -70°C to -80°C over approximately 0.5 hours. Maintain the temperature at -70°C to -80°C for 0.5 hours. Add 14.07 g of S11 and a solution prepared with 30 mL of tetrahydrofuran dropwise over approximately 0.5 hours. After the addition is complete, allow the temperature to rise naturally to room temperature. Acidify with 8 mL of concentrated hydrochloric acid, add 50 mL of ethyl acetate, separate the liquid, wash the organic phase until neutral, evaporate the solvent under vacuum, dissolve in 700 mL of heptane, pass through a 15 g silica gel column, concentrate the column chromatography solution to approximately 60 mL at atmospheric pressure, cool to room temperature, and filter. The yield was 8.55 g after drying, with a yield of 44%. The product was designated M4-1.

[0118] (5) Add 8.55 g of M4-1 and 100 mL of dichloromethane to a 0.5 L three-necked flask, start stirring, and cool to -15 °C under nitrogen protection. Control the temperature from -10 °C to -15 °C and add 5.52 g of boron tribromide dropwise over approximately 0.5 hours. After the addition is complete, allow the temperature to rise naturally to room temperature. Perform TLC staining; no starting material was found. Perform hydrolysis, separate the liquid and liquid phases, wash the organic phase until neutral, evaporate the solvent under normal pressure, add 30 mL of heptane, and stir for 0.5 hours. Filter. The yield after drying is 7.40 g, with a yield of 90%. The product is designated as M4-2.

[0119] (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. Stirring was started, and the mixture was cooled to -5 °C under nitrogen protection. The temperature was then controlled from 0 °C to -5 °C, and 7.25 g of trifluoromethanesulfonic anhydride was added dropwise over approximately 0.5 hours. After the addition was complete, the mixture was allowed to cool naturally to room temperature. TLC was performed; no starting material was found. The mixture 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. The crystals were filtered. The yield was 8.87 g after drying, with a yield of 88%. The product was designated as M4.

[0120] 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).

[0121] Example 5: Synthesis of intermediate M5

[0122] (1) Using compounds replace By selecting a suitable material ratio and referring to steps 2 and 3 of Example 4, S13 is obtained;

[0123] (2) S13 reacts with S9, following the synthetic procedure described in steps 4-6 of Example 4, to obtain intermediate M5. Product MS (m / e): 656.

[0124] Example 6: Synthesis of intermediate M6

[0125] By replacing S9 with compound S2 and selecting an appropriate material ratio, while keeping all other raw materials and steps the same as in Example 4, intermediate M6 was obtained. Product MS (m / e): 542.

[0126] Example 7: Synthesis of intermediate M7

[0127] (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. The mixture was stirred and heated to 105 °C to 110 °C and refluxed for 8 hours. The reaction was observed by TLC. No raw material was found. 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. The quantity was 56.03 g, and the yield was 96%. The product was designated as S14.

[0128] (2) Add 56.03 g of S14, 11.1 g of 2-bromobenzaldehyde and 120 mL of tetrahydrofuran to a 500 mL three-necked reaction flask. Under nitrogen protection, cool down to 0 °C to -5 °C. Control the temperature at 0 °C to -5 °C and add dropwise a solution prepared with 10.75 g of potassium tert-butoxide and 80 mL of tetrahydrofuran. The process takes about 1 hour. Keep the temperature at 0 °C to -5 °C for 1 hour. Perform TLC spotting. No raw material was found. Add 20 mL of concentrated hydrochloric acid below 0 °C and stir for 5 minutes. Add 100 mL of ethyl acetate, let stand and separate the liquid. Wash the organic phase until neutral. Vacuum evaporate the solvent. Dissolve the residue in 650 mL of hot column chromatography at 60 °C. Concentrate the column chromatography solution to 70 mL, cool to room temperature, filter, and dry. The quantity is 18.75 g, and the yield is 81%. The product is designated as S15.

[0129] (3) Referring to step 4 of Example 1, compound S15 reacts with S3 to obtain intermediate M7.

[0130] 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).

[0131] Example 8: Synthesis of intermediate M8

[0132] (1) Using compounds replace By selecting a suitable material ratio, and with other raw materials and steps being the same as in Example 7, intermediate S17 was obtained.

[0133] (2) Referring to steps 4-6 of Example 4, select a suitable material ratio, and react S17 and S13 to obtain intermediate M8. Product MS (m / e): 654.

[0134] Example 9: Synthesis of intermediate M9

[0135] Referring to steps 4-6 of Example 4, a suitable material ratio was selected, and S15 reacted with S11 to obtain intermediate M9. Product MS (m / e): 540.

[0136] Compound synthesis examples:

[0137] Synthesis Example 1: Synthesis of Compound C3

[0138] The synthesis route is as follows:

[0139] Specific synthesis steps:

[0140] A 1L three-necked flask equipped with a magnetic stirrer was purged with nitrogen, and then potassium tert-butoxide (11.2 g, 0.1 mol), D3 (33.2 g, 0.1 mol), and 400 mL of toluene were added sequentially. After another nitrogen purging, (0.4 g, 2 mmol) of tri-tert-butylphosphine and (0.2 g, 1 mmol) of palladium acetate were added sequentially. After the additions were complete, the mixture was heated to 85 °C. A solution consisting of (39.4 g, 0.1 mol) of M1 and 100 mL of toluene was then added dropwise, and the reaction was carried out at 80-120 °C for 4 hours until the reaction was complete. The mixture was adjusted to neutral, the organic phase was separated, extracted, dried, subjected to column chromatography, and the solvent was evaporated to dryness, yielding 48.3 g of a white solid, with a yield of approximately 70%.

[0141] 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).

[0142] Synthesis Example 2: Synthesis of Compound C15

[0143] The synthesis route is as follows:

[0144] Specific synthesis steps:

[0145] (1) In a 1L reaction flask, add M1 (55.29g, 140mmol), pinacol diborate (42.66g, 168mmol), and toluene (600mL), purge with nitrogen and stir for 15 minutes. Then add potassium acetate (41.22g, 420mmol), tris(dibenzyl indeneacetone)palladium (2.59g), and X-Phos (2.66g), and heat under reflux for 3 hours until the reaction is complete. Separate by silica gel short column chromatography, elute with hot toluene, and remove solvent from the organic phase; hot slurry with ethanol to obtain 57.21g of C15-1 white solid, yield 84%.

[0146] (2) In a 1 L reaction flask, 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. The mixture was heated 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. Recrystallization from n-heptane yielded 37.06 g of C15-2 white solid, with a yield of 78%.

[0147] (3) Replace intermediate D3 with intermediate D1 and M1 with C15-2, select a suitable material ratio, and keep the other raw materials and steps the same as in synthesis example 1 to obtain the target compound C15.

[0148] 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).

[0149] Synthesis Example 3: Synthesis of Compound C26

[0150] The synthesis route is as follows:

[0151] Specific synthesis steps:

[0152] (1) Replace M1 with 3,6-dibromo-9H-carbazole and D3 with D11. Select a suitable material ratio. Other raw materials and steps are the same as in Synthesis Example 1. Intermediate C26-1 is obtained.

[0153] (2) Replace intermediate D3 with intermediate C26-1, select a suitable material ratio, and keep the other raw materials and steps the same as in synthesis example 1 to obtain compound C26.

[0154] Product MS (m / e): 1079. 1H 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).

[0155] Synthesis Example 4: Synthesis of Compound C35

[0156] The synthesis route is as follows:

[0157] Specific synthesis steps:

[0158] (1) Replace M1 with 3-bromocarbazole and D3 with triphenylchlorosilane, select a suitable material ratio, and keep the other raw materials and steps the same as in Example 1 to obtain intermediate D26-1;

[0159] (2) Replace M1 and D3 with 3-bromocarbazole and D26-1 respectively, select a suitable material ratio, and keep the other raw materials and steps the same as in Synthesis Example 1 to obtain intermediate D26;

[0160] (3) D26 was used instead of D3. A suitable material ratio was selected. Other raw materials and steps were the same as in Example 1 of synthesis. The target compound C35 was obtained. The MS (m / e) of the product was 948.

[0161] Synthesis Example 5: Synthesis of Compound C66

[0162] The synthesis route is as follows:

[0163] Specific synthesis steps:

[0164] (1) M1 and D3 were replaced by 3-bromocarbazole and 10,10-diphenyl-5,10-dihydrodibenzo[b,e][1,4]azasilioline, respectively. With a suitable material ratio selected, the other raw materials and steps were the same as in Synthesis Example 1, and intermediate D21 was obtained.

[0165] (2) Replace M1 and D3 with M3 and D21 respectively, select appropriate material ratios, and keep the other raw materials and steps the same as in Synthesis Example 1 to obtain the target compound C66; product MS(m / e): 872.

[0166] Synthesis Example 6: Synthesis of Compound C96

[0167] The synthesis route is as follows:

[0168] Specific synthesis steps:

[0169] M1 and D3 were replaced with M2 and D15 respectively, and an appropriate material ratio was selected. All other raw materials and steps were the same as in Synthesis Example 1, to obtain the target compound C96. Product MS (m / e): 802.

[0170] Synthesis Example 7: Synthesis of Compound C109

[0171] The synthesis route is as follows:

[0172] Specific synthesis steps:

[0173] (1) Under nitrogen protection, M1 (19.4 g, 0.1 mol), pinacol diborate (30.5 g, 0.12 mol), potassium acetate (19.6 g, 0.2 mol), 0.3 g tris(dibenzylacetone)palladium, 0.3 g X-phos, and 300 ml dioxane were added to a 2 L three-necked flask. The mixture was heated and refluxed at 104 °C for 4 h. After the reaction solution cooled to room temperature, 300 ml toluene and 300 ml water were added, and the mixture was stirred for 10 min. The mixture was allowed to stand and separated, extracted, and the organic phases were combined, washed with water until neutral, and subjected to column chromatography. The solvent was evaporated, and the mixture was recrystallized from toluene:ethanol in a 1:3 ratio. The solution was filtered and dried to obtain 46.7 g of pale yellow solid C109-1, with a yield of 96%.

[0174] (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, and 100 ml anhydrous ethanol were added to a 2 L 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 70℃~75℃. After the addition was complete, the mixture was refluxed at 70℃~75℃ for 20 h. The reaction solution was cooled to room temperature, filtered, slurried twice with ethanol, dissolved in toluene, and column chromatography was performed. The solvent was evaporated to dryness. The mixture was recrystallized with 4 times toluene and 4 times heptane, filtered, and dried to obtain 55.4 g of white solid C109, with a yield of 72%.

[0175] Product MS (m / e): 769. 1H 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).

[0176] Synthesis Example 8: Synthesis of Compound C151

[0177] The synthesis route is as follows:

[0178] Specific synthesis steps:

[0179] (1) Replace M1 with M4, select a suitable material ratio, and keep the other raw materials and steps the same as step 1 of synthesis example 2 to obtain intermediate C151-1;

[0180] (2) Replace C109-1 with C151-1, select an appropriate material ratio, and follow the same raw materials and steps as in step 2 of Example 7 to obtain the target compound C151. Product MS (m / e): 769.

[0181] Synthesis Example 9: Synthesis of Compound C157

[0182] The synthesis route is as follows:

[0183] Specific synthesis steps:

[0184] (1) Replace M1 with M5, use 2 times the amount of pinacol diborate, select a suitable material ratio, and the other raw materials and steps are the same as step 1 of synthesis example 2 to obtain intermediate C157-1.

[0185] By replacing C109-1 and 9,9'(6-chloro-1,3,5-triazine)bis(9H-carbazole) with C157-1 and 2-chloro-4,6-diphenyl-1,3,5-triazine, and selecting a suitable material ratio, the other raw materials and steps were the same as in step 2 of Example 7, and the target compound C157 was obtained.

[0186] Product MS (m / e): 822. 1H 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).

[0187] Synthesis Example 10: Synthesis of Compound C164

[0188] The synthesis route is as follows:

[0189] Specific synthesis steps:

[0190] (1) Replace M1 with M6, select a suitable material ratio, and keep the other raw materials and steps the same as step 1 of synthesis example 2 to obtain intermediate C164-1;

[0191] (2) Replace C109-1 with C164-1, replace 9,9'(6-chloro-1,3,5-triazine)bis(9H-carbazole) with 2-chloro-4,6-diphenyl-1,3,5-triazine, select a suitable material ratio, and the other raw materials and steps are the same as in step 2 of synthesis example 7 to obtain intermediate C164-2.

[0192] (3) Replace M1 and D3 with C164-2 and D8 respectively, select an appropriate material ratio, and keep the other raw materials and steps the same as in Synthesis Example 1 to obtain the target compound C164.

[0193] 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).

[0194] Synthesis Example 11: Synthesis of Compound C195

[0195] The synthesis route is as follows:

[0196] Specific synthesis steps:

[0197] M1 and D3 were replaced with M7 and D21 respectively, and a suitable material ratio was selected. All other raw materials and steps were the same as in Synthesis Example 1, and the target compound C195 was obtained.

[0198] 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).

[0199] Synthesis Example 12: Synthesis of Compound C243

[0200] The synthesis route is as follows:

[0201] Specific synthesis steps:

[0202] M1 and D3 were replaced with M8 and D8 respectively, and a suitable material ratio was selected. All other raw materials and steps were the same as in Synthesis Example 1, and the target compound C243 was obtained.

[0203] 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).

[0204] Synthesis Example 13: Synthesis of Compound C253

[0205] The synthesis route is as follows:

[0206] Specific synthesis steps:

[0207] Using M9 instead of M6, and selecting a suitable material ratio, the other raw materials and steps were the same as in Synthesis Example 10, to obtain the target compound C253; product MS (m / e): 762.

[0208] Synthesis Example 14: Synthesis of Compound C256

[0209] The synthesis route is as follows:

[0210] Specific synthesis steps:

[0211] (1) Referring to step (2) of Synthesis Example 7, 2.05 equivalents of 9-(4-(4,4,5,5-tetramethyl-1,3,2-dioxoboronyl-2-yl)phenyl)-9H-carbazole were reacted with 1 equivalent of 2,4,6-trichloro-1,3,5-triazine to give intermediate C256-1 in 55% yield;

[0212] (2) Replace 9,9'(6-chloro-1,3,5-triazine-2,4-diyl)bis(9H-carbazole) with C256-1, and the other raw materials and steps are the same as in the synthesis example 7, to obtain the target compound C256.

[0213] 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).

[0214] Those skilled in the art should understand that the above preparation method is merely an exemplary example, and they can obtain other compound structures of the present invention by improving it.

[0215] Device Example 1

[0216] First, the glass substrate, which has a 120 nm thick indium tin oxide (ITO) anode, is cleaned and then treated with UV ozone and oxygen plasma. After treatment, the substrate is dried in a nitrogen-filled glove box to remove moisture, and then mounted on a substrate holder and placed in a vacuum chamber. The organic layer specified below is applied at a vacuum degree of approximately 10... -8 In the case of Torr, The deposition rate was achieved sequentially on the ITO anode via thermal vacuum. Simultaneously, the deposition compounds HT and NDP-9 (weight ratio 97:3) were used as a hole injection layer (HIL) with a thickness of [missing information]. Compound HT is used as a hole transport layer (HTL) with a thickness of [missing information]. Compound EB is used as an electron blocking layer (EBL) with a thickness of [missing information]. Then, compound C3 from synthesis example 1 was used as the blue light host and BD as the dopant (weight ratio 98:2), and co-deposited as the emissive layer (EML) with a thickness of [missing information]. Compound HB was used as the hole blocking layer (HBL), with a thickness of [missing information]. On the hole-blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-deposited (weight ratio 50:50) as an electron transport layer (ETL), with a thickness of [missing information]. Finally, vapor deposition Thick 8-hydroxyquinoline-lithium (Liq) was used as the electron injection layer (EIL) and deposited by evaporation. Aluminum was used as the cathode. The device was then transferred back to the glove box and sealed with a glass cover to complete the device.

[0217] Device Examples 2 to 14

[0218] The method is the same as in Device Example 1, except that in the light-emitting layer (EML), compounds C15, C26, C35, C66, C96, C109, C151, C157, C164, C195, C243, C253 and C256 synthesized in Synthesis Examples 2 to 13 in Table 1 are used instead of compound C3 as the main material for blue light.

[0219] Device Comparison Example 1

[0220] The method is the same as in Device Example 1, except that compound A is used instead of compound C3 as the main material for blue light emission in the emissive layer (EML).

[0221] The material structure used in the device is shown below:

[0222] Table 1 lists the values ​​at 10 mA / cm 2 Under the given conditions, the voltage (V), external quantum efficiency (EQE), and lifetime (T) were measured. To better illustrate the data comparison, the voltage, efficiency, and lifetime of Comparative Example 1 were set to 100%. The voltage, efficiency, and lifetime data of Device Examples 1 to 14 were all converted relative to the corresponding data of Comparative Example 1. The relevant data and conversion results are shown in Table 1.

[0223] Table 1

[0224] As shown in Table 1, at 10 mA / cm 2 At current density, compared with Comparative Example 1, Device Examples 1 to 14 can reduce voltage by 4% to 19%, improve external quantum efficiency by 1% to 35%, and extend device lifetime by 3% to 23%.

[0225] The above data show that the silicon-containing seven-membered spirocyclic compound synthesized in this invention, compared with comparative example compound A, has a lower driving voltage and higher current efficiency and lifetime compared with compound A due to the introduction of seven-membered cyclic silicon atoms in the structure. This structural change brings excellent device performance and is unexpected, proving the unique advantages of the compound of this invention.

[0226] It should be understood that the various embodiments described herein are merely examples and are not intended to limit the scope of the 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 can be substituted with other materials and structures without departing from the spirit of the invention. It should be understood that various theories regarding why the invention works are not intended to be limiting.

Claims

1. A heterocyclic compound of formula I: ###0001### I wherein L A , L B , L C and L D are each independently selected from a single bond, a substituted or unsubstituted arylene having 6-30 carbon atoms, a substituted or unsubstituted heteroarylene having 3-30 carbon atoms, or a combination thereof; R A , R B , R C , and R D are each independently selected from substituted or unsubstituted monocyclic nitrogen-containing heteroaryl having 3-18 carbon atoms, substituted or unsubstituted polycyclic nitrogen-containing heteroaryl having 6-30 carbon atoms; each of n1, n2, n3, and n4 is independently 0, 1, 2, 3, or 4, and n1, n2, n3, and n4 are not simultaneously 0; represents a single or double bond; when L A , L B , L C , L D , R A , R B , R C and R D have substituents, said substituents are one or more, and each independently selected from deuterium, halogen, substituted or unsubstituted alkyl of 1-20 carbon atoms, substituted or unsubstituted deuterated alkyl of 1-20 carbon atoms, substituted or unsubstituted haloalkyl of 1-20 carbon atoms, substituted or unsubstituted cycloalkyl of 3-20 carbon atoms, substituted or unsubstituted deuterated cycloalkyl of 3-20 carbon atoms, substituted or unsubstituted halocycloalkyl of 3-20 carbon atoms, substituted or unsubstituted heteroalkyl of 1-20 carbon atoms, substituted or unsubstituted heterocycloalkyl of 3-20 carbon atoms, substituted or unsubstituted aralkyl of 7-30 carbon atoms, substituted or unsubstituted alkoxy of 1-20 carbon atoms, substituted or unsubstituted aryl of 6-30 carbon atoms, substituted or unsubstituted aryloxy of 6-30 carbon atoms, substituted or unsubstituted heteroaryl of 3-30 carbon atoms, substituted or unsubstituted alkenyl of 2-20 carbon atoms, substituted or unsubstituted alkynyl of 2-20 carbon atoms, substituted or unsubstituted alkylsilyl of 3-20 carbon atoms, substituted or unsubstituted arylsilyl of 6-20 carbon atoms, substituted or unsubstituted amino of 0-20 carbon atoms, acyl, carbonyl, carboxylic acid, ester, cyano, isocyano, hydroxy, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.

2. The compound of claim 1, wherein L A , L B , L C and L D are each independently selected from a single bond, a substituted or unsubstituted arylene having from 6 to 20 carbon atoms, a substituted or unsubstituted heteroarylene having from 3 to 20 carbon atoms, or a combination thereof; Preferably, L A , L B , L C , and L D are each independently selected from a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted carbazolylene, or a combination thereof; when L A , L B , L C , and L D have substituents, the substituents are one or more, and are each independently selected from the group consisting of deuterium, halogen, alkyl of 1-10 carbon atoms, deuterated alkyl of 1-10 carbon atoms, halogenated alkyl of 1-10 carbon atoms, cycloalkyl of 3-10 carbon atoms, deuterated cycloalkyl of 3-10 carbon atoms, halogenated cycloalkyl of 3-10 carbon atoms, aryl of 6-18 carbon atoms, heteroaryl of 3-18 carbon atoms, alkylsilyl of 3-10 carbon atoms, arylsilyl of 6-20 carbon atoms, and combinations thereof; Preferably, L A , L B , L C and L D are each independently selected from a single bond, a substituted or unsubstituted group W, wherein 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 the group consisting of deuterium, halogen, alkyl having 1-10 carbon atoms, deuterated alkyl having 1-10 carbon atoms, halogenated alkyl having 1-10 carbon atoms, alkylsilyl having 3-10 carbon atoms, arylsilyl having 6-20 carbon atoms; preferably deuterium, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, trimethylsilyl, and triphenylsilyl; denotes the position of attachment of the phenyl ring of the compound of formula I, represents the position of attachment to R A , R B , R C or R D .

3. The compound of claim 1 or 2, wherein L A , L B , L C and L D are each independently selected from the group consisting of a single bond or the following group of radicals: Preferably, L A , L B , L C and L D are each independently selected from the group consisting of a single bond or the following group of radicals: denotes the position of attachment of the phenyl ring of the compound of formula I, represents the position of attachment to R A , R B , R C or R D .

4. The compound according to any one of claims 1 to 3, characterized in that, R A , R B , R C and R D are each independently selected from a substituted or unsubstituted group Z, wherein unsubstituted group Z is selected from structures shown in formula III-1 to III-3; in Formula III-1 and Formula III-2, X is independently selected from the group consisting of a single bond, O, S, CR1R2, or SiR1R2; in Formula III-3, each of X1, X2, X3 is independently selected from the group consisting of CH and N, and at least one of X1, X2, and X3 is N; R1and R2are each independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl having 1-20 carbon atoms, deuterated alkyl having 1-20 carbon atoms, halogenated alkyl having 1-20 carbon atoms, cycloalkyl having 3-20 carbon atoms, deuterated cycloalkyl having 3-20 carbon atoms, halogenated cycloalkyl having 3-20 carbon atoms, heteroalkyl having 1-20 carbon atoms, heterocycloalkyl having 3-20 carbon atoms, aralkyl having 7-30 carbon atoms, alkoxy having 1-20 carbon atoms, aryl having 6-30 carbon atoms, aryloxy having 6-30 carbon atoms, heteroaryl having 3-30 carbon atoms, alkenyl having 2-20 carbon atoms, alkynyl having 2-20 carbon atoms, alkylsilyl having 3-20 carbon atoms, arylsilyl having 6-20 carbon atoms, amino having 0-20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, hydroxyl, thiol, sulfinyl, sulfonyl, phosphino, and combinations thereof; Preferably, R1and R2are each independently selected from the group consisting of hydrogen, deuterium, alkyl having 1-10 carbon atoms, deuterated alkyl having 1-10 carbon atoms, halogenated alkyl having 1-10 carbon atoms, cycloalkyl having 3-10 carbon atoms, deuterated cycloalkyl having 3-10 carbon atoms, halogenated cycloalkyl having 3-10 carbon atoms, aralkyl having 7-20 carbon atoms, aryl having 6-20 carbon atoms, and combinations thereof; wherein when the group Z contains a substituent, the substituent is one or more, and each is independently selected from the group consisting of deuterium, halogen, alkyl having 1-10 carbon atoms, deuterated alkyl having 1-10 carbon atoms, halogenated alkyl having 1-10 carbon atoms, cycloalkyl having 3-10 carbon atoms, deuterated cycloalkyl having 3-10 carbon atoms, halogenated cycloalkyl having 3-10 carbon atoms, aryl having 6-18 carbon atoms, heteroaryl having 3-18 carbon atoms, alkylsilyl having 3-10 carbon atoms, arylsilyl having 6-20 carbon atoms, and combinations thereof.

5. The compound of claim 4, wherein The unsubstituted group Z is selected from the group consisting of the following formulae: represents the position of attachment to L A , L B , L C or L D ​ Preferably, when the group Z contains a substituent, the substituent is one or more, and each is independently selected from the group consisting of deuterium, halogen, alkyl having 1-10 carbon atoms, deuterated alkyl having 1-10 carbon atoms, halogenated alkyl having 1-10 carbon atoms, aryl having 6-18 carbon atoms, heteroaryl having 3-18 carbon atoms, alkylsilyl having 3-10 carbon atoms, arylsilyl having 6-20 carbon atoms, and combinations thereof; preferably deuterium, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, phenyl, biphenyl, naphthyl, anthryl, phenanthryl, dibenzofuranyl, dibenzothiophenyl, carbazolyl, fluorenyl, trimethylsilyl, triphenylsilyl, N-phenylcarbazolyl, and combinations thereof; Preferably, R A , R B , R C and R D are each independently selected from the group consisting of the following structures:

6. The compound according to any one of claims 1 to 5, wherein The compounds have the structures shown below in Formula I-1 through Formula I-8: wherein L A , L B , L C , L D , R A , R B , R C and R D are as defined in any one of claims 1 to 5, and each of n1, n2, n3 and n4 is independently 1 or 2. Preferably, each independently selected from the group consisting of the following structures:

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

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

9. An organic electroluminescent device comprising an anode, a cathode, and an emitting layer disposed between the anode and the cathode, wherein the host material of the emitting layer contains a 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, an electron injection layer.

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

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