Silicon-containing compound and organic electroluminescent device thereof

Abstract

The invention relates to a silicon-containing compound and an organic electroluminescent device thereof, and belongs to the technical field of organic photoelectric materials. The invention mainly solves the problem that the transmission speeds of holes and electrons are not matched, so that the recombination probability of the holes and the electrons in a light-emitting layer is greatly reduced, and the performance of the organic light-emitting device is reduced. When the silicon-containing compound provided by the invention is used as an electron transport layer material, the silicon-containing compound has relatively high electron mobility; when the material is used as a hole blocking layer material, holes can be effectively prevented from migrating to one side of an electron transport layer. When the compound is applied to the organic light-emitting device, the compound probability of holes and electrons in a light-emitting layer can be effectively improved, so that the service life of the organic light-emitting device is prolonged, the light-emitting efficiency of the organic light-emitting device is improved, and the driving voltage of the device is reduced.

Description

Technical Field

[0001] This invention relates to the field of organic optoelectronic materials technology, specifically to a silicon-containing compound and its organic electroluminescent device. Background Technology

[0002] With the rapid development of science and technology, emerging industries such as new energy, new materials, information technology, and biotechnology have risen rapidly, greatly changing people's work and lives. Today, organic light-emitting diodes (OLEDs), based on information and new materials technologies, are widely used in small and medium-sized displays such as mobile phone screens and data instruments. Meanwhile, large-size full-color flat panel display technology is also gradually maturing. Undoubtedly, OLED has become a strong competitor to second-generation liquid crystal displays (LCDs), and it is believed that OLED will occupy a larger and more significant market share in the future.

[0003] Organic light-emitting diodes (OLEDs) convert electrical energy into light by applying electricity to organic light-emitting materials, and typically consist of an anode, a cathode, and an organic layer formed between these two electrodes. The organic layer of an OLED can include a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer (containing host material and dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer, etc. The materials used in the organic layer can be categorized according to their function as hole injection materials, hole transport materials, electron blocking materials, light-emitting materials, electron buffer materials, hole blocking materials, electron transport materials, and electron injection materials. In OLEDs, holes from the anode and electrons from the cathode are injected into the light-emitting layer by applying a voltage, and the recombination of holes and electrons generates excitons with high energy. The organic light-emitting compound moves to an excited state by energy and emits light by the energy when the organic light-emitting compound returns from the excited state to the ground state.

[0004] The main problem currently facing organic electroluminescent devices is that, due to the different properties of the materials, the hole transport efficiency in the hole transport layer is much higher than that in the electron transport layer. This greatly reduces the probability of electron-hole recombination in the light-emitting layer, thereby reducing the device's luminous efficiency and lifespan. Therefore, there is an urgent need to develop materials with efficient electron injection and transport capabilities, and the ability to block holes to facilitate recombination between holes and electrons in the light-emitting layer. Summary of the Invention

[0005] To address the above problems, the present invention provides a silicon-containing compound and its organic electroluminescent device.

[0006] This invention provides a silicon-containing compound, as shown in Formula 1: ; in, The x is independently selected from C(R2) or N, and at least two x are N; The z is independently selected from C(R3) or N, and at least two z are N; The Ara, Arb, Arc, and Ard are independently selected from any one of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C6-C30 aromatic rings, and C3-C15 alicyclic fused cycloalloys. Furthermore, the "substituted or unsubstituted..." groups of Ara, Arb, Arc, and Ard are selected from any one of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, fused cycloalkanes of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings; L1 and L2 are each independently selected from any one or a combination of single-bonded, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl. The L3 is selected from any one or a combination of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups; The R0 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl; The n is selected from 1, 2, or 3; R1, R2, and R3 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring, and fused cycloalkanes of C3-C15 alicyclic rings; The La, Lb, Lc, and Ld are independently selected from single bonds, any one of the following groups, or a combination thereof: ; The value of k is selected from 1, 2, 3, or 4; The u is independently selected from C(R) 12 ) or N; The U is selected from C(R) 13 R 14 ) or N(R 15 ); The ring A is selected from substituted or unsubstituted C3-C15 alicyclic rings; X3 is selected from O, S, or N(R) 16 ); Q1 is selected from C(R) 17 ) or N; The R 11 R 12 Independently selected from any one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcohols of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings, or two adjacent R groups. 12 The links form substituted or unsubstituted rings; The R 13 R 14 Independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcohols of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings, or R 13 R 14 The links form substituted or unsubstituted rings; The R 15 R 16 R 17 The independent group is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C15 alicyclic fused cycloalcohol.

[0007] The present invention also provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside at least one electrode of the cathode or the anode, and the organic layer comprises any one of the silicon-containing compounds described in the present invention.

[0008] Beneficial effects: The silicon-containing compound provided by this invention exhibits high electron mobility when used as an electron transport layer material, thereby improving the binding efficiency of holes and electrons. When used as a hole blocking layer material, it effectively blocks holes from migrating to the electron transport layer side. Its application in devices can improve luminous efficiency, lifespan, and reduce driving voltage. Detailed Implementation

[0009] The technical solutions of this invention will be clearly and completely described below with reference to specific embodiments. Obviously, the described embodiments are only a part of the embodiments of this invention, and not all of them. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of this invention.

[0010] The halogens mentioned in this invention refer to fluorine, chlorine, bromine, and iodine.

[0011] The alkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from an alkane molecule. It can be a straight-chain alkyl group or a branched-chain alkyl group, preferably having 1 to 15 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms. The straight-chain alkyl group includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, etc., but is not limited thereto. The branched-chain alkyl group includes isopropyl, isobutyl, sec-butyl, tert-butyl, isomeric groups of n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, etc., but is not limited thereto. The alkyl group is preferably methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.

[0012] The cycloalkyl group described in this invention refers to a hydrocarbon group formed by removing one hydrogen atom from a cycloalkane molecule, preferably having 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 5 to 10 carbon atoms. Examples may include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornane, etc., but are not limited thereto. The aforementioned cycloalkyl groups are preferably cyclopentane, cyclohexane, cyclopentenyl, 1-adamantane, 2-adamantane, and norbornane.

[0013] The alicyclic hydrocarbons described in this invention refer to aliphatic hydrocarbons, which may be completely unsaturated or partially unsaturated. Preferably, they have 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, and particularly preferably 3 to 10 carbon atoms. Examples include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited thereto. Multiple monocyclic hydrocarbons can also be linked in various ways: two rings in the molecule can share a carbon atom to form a spirocyclic ring; two carbon atoms on a ring can be connected by a carbon bridge to form a bridged ring; several rings can also be interconnected to form a cage-like structure. Examples include adamantane, norbornane, camphene, etc., but are not limited thereto.

[0014] The aryl group mentioned in this invention refers to the general term for the monovalent group remaining after removing a hydrogen atom from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic aryl, polycyclic aryl, or fused-ring aryl, preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 14 carbon atoms, and most preferably 6 to 12 carbon atoms. The monocyclic aryl group refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited to this; the polycyclic aryl group refers to an aryl group with two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited to this; the fused-ring aryl group refers to an aryl group with two or more aromatic rings in the molecule that are fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, peryl, thionyl, fluorenyl, benzo[a]fluorenyl, triphenylene, fluoranyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, etc., but not limited to this. The fused aryl and aliphatic ring group refers to a group containing one or more aromatic rings and one or more aliphatic rings in the molecule, such as tetrahydronaphthyl, indene, etc., but not limited thereto. The aryl group is preferably phenyl, biphenyl, terphenyl, 1-naphthyl, 2-naphthyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, or spiro-cyclohexenyl-fluorenyl.

[0015] The heteroaryl group described in this invention refers to a group obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms. The heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, silicon, selenium, or phosphorus atoms, preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 3 to 15 carbon atoms, and most preferably 3 to 12 carbon atoms. The linking site of the heteroaryl group can be located on a cyclic carbon atom or a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, polycyclic heteroaryl, or fused-ring heteroaryl. Monocyclic heteroaryl groups include pyridyl, pyrimidinyl, triazine, furanyl, thiophene, pyrrole, imidazolyl, etc., but are not limited to these. Polycyclic heteroaryl groups include bipyridyl, bipyrimidinyl, phenylpyridinyl, etc., but are not limited to these. Fused-ring heteroaryl groups include quinolinyl, isoquinolinyl, etc., but are not limited to these. The aforementioned heteroaryl groups are preferably pyridyl, pyrimidinyl, thiophene, furanyl, benzothiophene, benzofuranyl, benzooxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophene, benzodibenzothiophene, benzodibenzofuranyl, carbazolyl, acridinel, phenoxazinyl, phenthiazinyl, and phenoxthialyl.

[0016] The silyl group described in this invention refers to a monovalent group formed by removing a hydrogen atom from a silane molecule, and can be represented by the group described in —Si(R)(R)(R), where R is selected from hydrogen, deuterium, cyano, halogen, or any one or more of the alkyl, cycloalkyl, aryl, and heteroaryl groups described above. Examples may include trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropanesilyl, tricyclobutanesilyl, triphenylsilyl, triphenylsilyl, etc., but are not limited thereto.

[0017] In this invention, the term "aryl" refers to an aryl group having two bonding sites, i.e., a divalent group. They are otherwise divalent groups, and the description of aryl groups described above applies.

[0018] In this invention, the term "hybrid aryl" refers to a heteroaryl group having two bonding sites, i.e., a divalent group. Apart from being divalent groups, they are subject to the above description of heteroaryl groups.

[0019] The term "substitution" as used in this invention refers to the replacement of a hydrogen atom in certain functional groups by another atom or functional group (i.e., a substituent), and the position of substitution is not limited, as long as the position is where the hydrogen atom is substituted. Furthermore, when two or more are substituted, the two or more substituents may be the same as or different from each other.

[0020] In this invention, "substituted or unsubstituted" means unsubstituted or substituted by one or more substituents selected from the group consisting of: deuterium, tritium, halogen, amino, cyano, nitro, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 cycloalkenyl, substituted or unsubstituted C3-C30 heterocyclic, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C2-C60 heteroaryl, silyl, preferably deuterium, tritium, halogen, cyano, nitro, C1-C12 alkyl, C3 ... Cycloalkyl, C3-C12 cycloalkenyl, C3-C12 heterocyclic, C6-C30 aryl, C3-C30 heteroaryl, silyl, when substituted with multiple substituents, the multiple substituents may be the same or different from each other; preferably, it means unsubstituted or substituted with one or more substituents selected from the group consisting of: deuterium, tritium, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, trifluoromethyl, deuterated methyl, ethyl, deuterated ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, deuterated tert-butyl, cyclopropane, methyl-substituted cyclopropane, ethyl-substituted cyclopropane, deuterated cyclopropane, cyclobutane, methyl-substituted cyclobutane, ethyl-substituted cyclobutane, deuterated Cyclobutyl, cyclopentyl, methyl-substituted cyclopentyl, ethyl-substituted cyclopentyl, deuterated cyclopentyl, cyclohexyl, methyl-substituted cyclohexyl, ethyl-substituted cyclohexyl, n-propyl-substituted cyclohexyl, n-butyl-substituted cyclohexyl, cyclohexane-substituted cyclohexyl, deuterated cyclohexyl, cycloheptyl, cyclopentenyl, methyl-substituted cyclopentenyl, ethyl-substituted cyclopentenyl, cyclohexenyl, cycloheptenyl, adamantyl, methyl-substituted adamantyl, ethyl-substituted adamantyl, deuterated adamantyl, norbornyl, methyl-substituted norbornyl, ethyl-substituted norbornyl, deuterated norbornyl, tetrahydropyrrolyl, piperidinyl, morpholinyl, thiomorpholinyl, methyl-substituted piperazine, ethyl The substituted piperazine, phenyl-substituted piperazine, naphthyl-substituted piperazine, methoxy, ethoxy, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, anthracene, deuterated anthracene, phenanthrene, deuterated phenanthrene, triphenylene, pyrene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirodifluorenyl, spiro-cyclopentyl-fluorenyl, spiro-cyclohexyl-fluorenyl, spiro-adamantyl-fluorenyl, spiro-cyclopentenyl-fluorenyl, spiro-cyclohexenyl-fluorenyl, pyridyl, pyrimidinyl, triazine, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, N-phenylcarbazoyl, dibenzofuranyl, dibenzothiopheneyl, trimethylsilyl, triphenylsilyl, when substituted by multiple substituents, the multiple substituents may be the same as or different from each other.

[0021] In this invention, "adjacent groups linked to form a substituted or unsubstituted ring" refers to the formation of a substituted or unsubstituted aromatic ring, heteroaromatic ring, aliphatic ring, or aliphatic heterocycle by the combination of adjacent groups and optional aromatization. "Adjacent groups" refers to two substituents on two directly connected atoms, a substituent positioned spatially closest to the corresponding substituent, or another substituent on an atom with the corresponding substituent. For example, two substituents substituted at the ortho position of a benzene ring or two substituents on the same carbon atom in an aliphatic ring can be considered adjacent to each other. Examples are shown below: .

[0022] In this specification, when the position of the substituent on the ring is not fixed, it means that it can be attached to any of the corresponding optional sites on the ring. For example, Can represent , , ; Can represent , , ; Can represent , , , , , , , , , And so on.

[0023] In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that the substituent or linking site can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the ring. For example, Can represent or ; Can represent , And so on.

[0024] This invention provides a silicon-containing compound, which is shown in Formula 1: ; in, The x is independently selected from C(R2) or N, and at least two x are N; The z is independently selected from C(R3) or N, and at least two z are N; The Ara, Arb, Arc, and Ard are independently selected from any one of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C6-C30 aromatic rings, and C3-C15 alicyclic fused cycloalloys. Furthermore, the "substituted or unsubstituted..." groups of Ara, Arb, Arc, and Ard are selected from any one of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, fused cycloalkanes of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings; L1 and L2 are each independently selected from any one or a combination of single-bonded, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl. The L3 is selected from any one or a combination of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups; The R0 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl; The n is selected from 1, 2, or 3; R1, R2, and R3 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring, and fused cycloalkanes of C3-C15 alicyclic rings; The La, Lb, Lc, and Ld are independently selected from single bonds, any one of the following groups, or a combination thereof: ; The value of k is selected from 1, 2, 3, or 4; The u is independently selected from C(R) 12 ) or N; The U is selected from C(R) 13 R 14 ) or N(R 15 ); The ring A is selected from substituted or unsubstituted C3-C15 alicyclic rings; X3 is selected from O, S, or N(R) 16 ); Q1 is selected from C(R) 17 ) or N; The R 11 R12 Independently selected from any one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcohols of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings, or two adjacent R groups. 12 The links form substituted or unsubstituted rings; The R 13 R 14 Independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcohols of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings, or R 13 R 14 The links form substituted or unsubstituted rings; The R 15 R 16 R 17 The independent group is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C15 alicyclic fused cycloalcohol.

[0025] Preferably, the silicon-containing compound is selected from one of the following formulas 1-1 to 1-12: ; The R0 is independently selected from hydrogen, deuterium, substituted or unsubstituted groups of any one of the following: methyl, ethyl, n-propyl, n-butyl, isopropyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexyl, cyclooctyl, norbornyl, adamantyl; R1, L1, L2, L3, La, Lb, Lc, Ld, Ara, Arb, Arc, Ard, n, R2, and R3 are the same as those described in Equation 1.

[0026] Preferably, the " "Selected from any one of the following groups:" ; R1 is independently selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, naphthyl, phenyl-naphthyl, naphthyl-phenyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl. Quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, o-phenantholinyl, benzofuranyl, benzothiopheneyl, indyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9phenylfluorenyl, 9,9-spirodifluorenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropanesilyl, tricyclobutanesilyl, triphenylsilyl, triphenylsilyl.

[0027] Preferably, Ara, Arb, Arc, and Ard are independently selected from any one of the following groups: ; The Ra and Rb are independently selected from any one of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C15 alicyclic fused cycloalkanes, or two adjacent Ra are connected to form a substituted or unsubstituted ring; The Ry and Rt are independently selected from any one of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, or Rt and Ry are connected to form a substituted or unsubstituted alicyclic ring. The Rw is independently selected from any one of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C15 alicyclic fused cycloalcohol, or two adjacent Rws connected to form a substituted or unsubstituted ring; The a1 is independently selected from 1, 2, 3, 4 or 5; the a2 is independently selected from 1, 2, 3 or 4; the a3 is independently selected from 1, 2 or 3; the a4 is independently selected from 1 or 2; the a5 is independently selected from 1, 2, 3, 4, 5 or 6; the a6 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; the a7 is independently selected from 1, 2, 3, 4, 5, 6 or 7; and the a8 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

[0028] Preferably, Ra and Rb are independently selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, naphthyl, phenyl-naphthyl, naphthyl-phenyl, anthracene, phenanthrene, triphenylene, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropanesilyl, tricyclobutanesilyl, triphenylsilyl, terphenylsilyl.

[0029] More preferably, one, two, three, or four of Ara, Arb, Arc, and Ard are selected from any one of the following groups: .

[0030] Preferably, L1 and L2 are independently selected from single bonds, any one of the following groups, or a combination thereof: ; The q is selected from 1, 2, 3, or 4; The m is independently selected from C (Rc) or N; The V is selected from O, S, C (ReRf) or N (Rh); Z1 is independently selected from O, S, or N (Ri); The Rc and Rd are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcohols of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings, or adjacent Rc are connected to form a substituted or unsubstituted ring; The Re and Rf are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcohols of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings, or Re and Rf are connected to form substituted or unsubstituted rings; The Rh and Ri are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C15 alicyclic fused cycloyl group; The c1 is independently selected from 1 or 2, the c2 is independently selected from 1, 2, 3 or 4, the c3 is independently selected from 1, 2, 3, 4, 5 or 6, and the c4 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8.

[0031] More preferably, L1 and L2 are independently selected from single bonds, any one of the following groups, or a combination thereof: ; The Rc and Rd are independently selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, naphthyl, phenyl-naphthyl, naphthyl-phenyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl. Quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, o-phenantholinyl, benzofuranyl, benzothiopheneyl, indyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9phenylfluorenyl, 9,9-spirodifluorenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropanesilyl, tricyclobutanesilyl, triphenylsilyl, triphenylsilyl; The Rn and Rh are independently selected from hydrogen, deuterium, substituted or unsubstituted groups of any one of the following: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, naphthyl, phenyl-naphthyl, naphthyl-phenyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl Isoquinolinyl, quinazolinyl, quinoxolinyl, o-phenanthrolinel, benzofuranyl, benzothiopheneyl, indyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9phenylfluorenyl, 9,9-spirodifluorenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropanesilyl, tricyclobutanesilyl, triphenylsilyl, triphenylsilyl; The Re' and Rf' are independently selected from any one of the following groups, which are hydrogen, deuterium, cyano, halogen, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropanesilyl, tricyclobutanesilyl, triphenylsilyl, triphenylsilyl, or Re' and Rf' are linked to form substituted or unsubstituted alicyclic rings; The c1 is independently selected from 1 or 2, the c2 is independently selected from 1, 2, 3 or 4, the c3 is independently selected from 1, 2, 3, 4, 5 or 6, the c4 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8, the c5 is independently selected from 1, 2, 3, 4 or 5, and the c6 is independently selected from 1, 2 or 3.

[0032] Preferably, the L3 is selected from any one or a combination of the following groups: ; The v is independently selected from C(R5) or N; The A is selected from O, S, C (R6R7) or N (R8); The ring B is selected from substituted or unsubstituted C3-C15 alicyclic rings; Q2 is selected from C(R) 20 ) or N; X2 is selected from O, S or N (R9); The R5 and R4 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcohols of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings, or two adjacent R5s are connected to form a substituted or unsubstituted ring; The R6, R7, R 20 Independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C15 alicyclic fused cycloalcohol, or R6 and R7 linked to form a substituted or unsubstituted ring; R8 and R9 are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C15 alicyclic fused cycloalcohol.

[0033] More preferably, the L3 is selected from any one of the following groups: ; R4 and R5 are independently selected from any one of the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, naphthyl, phenyl-naphthyl, naphthyl-phenyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl. Quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, o-phenantholinyl, benzofuranyl, benzothiopheneyl, indyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9phenylfluorenyl, 9,9-spirodifluorenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropanesilyl, tricyclobutanesilyl, triphenylsilyl, triphenylsilyl; The R6' and R7' are independently selected from any one of the following groups, which are hydrogen, deuterium, cyano, halogen, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantane, norbornyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropanesilyl, tricyclobutanesilyl, triphenylsilyl, triphenylsilyl, or R6' and R7' are connected to form a substituted or unsubstituted alicyclic ring; The R8, R 10 Independently selected from any one of the following groups, which are hydrogen, deuterium, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, naphthyl, phenyl-naphthyl, naphthyl-phenyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, isoquinoline. alkyl, quinazolinyl, quinoxolinyl, o-phenanthrinyl, benzofuranyl, benzothiopheneyl, indyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9phenylfluorenyl, 9,9-spirodifluorenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropanesilyl, tricyclobutanesilyl, triphenylsilyl, triphenylsilyl; The d1 is independently selected from 1 or 2, the d2 is independently selected from 1, 2, 3 or 4, the d3 is independently selected from 1, 2, 3, 4, 5 or 6, the d4 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8, the d5 is independently selected from 1, 2, 3, 4 or 5, and the d6 is independently selected from 1, 2 or 3.

[0034] Preferably, the La, Lb, Lc, and Ld are independently selected from single bonds, any one of the following groups, or a combination thereof: ; The R 11 R 12 Independently selected from any one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcohols of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings, or two adjacent R groups. 12 The links form substituted or unsubstituted rings; The R 13 '、R 14 'Independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, or R 13 '、R 14 'Connection forms substituted or unsubstituted alicyclic rings;' The R 15 R 15 'Independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C15 alicyclic fused cycloalcoholic group; The number e1 is independently selected from 1, 2, 3, or 4; the number e2 is independently selected from 1, 2, or 3; the number e3 is independently selected from 1, 2, 3, 4, or 5; the number e4 is independently selected from 1 or 2; the number e5 is independently selected from 1, 2, 3, 4, 5, or 6; the number e6 is independently selected from 1, 2, 3, 4, 5, 6, 7, or 8; and the number e7 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

[0035] Preferably, the R 11 R 12Independently selected from any one of the following groups, whether hydrogen, deuterium, cyano, halogen, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, adamantyl, norbornel, phenyl, biphenyl, terphenyl, benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclopentenyl, benzocyclohexenyl, naphthyl, phenyl-naphthyl, naphthyl-phenyl, anthracene, phenanthrene, triphenylene, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, quinolinyl, Isoquinolinyl, quinazolinyl, quinoxolinyl, o-phenanthrolinel, benzofuranyl, benzothiopheneyl, indyl, dibenzofuranyl, dibenzothiopheneyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9phenylfluorenyl, 9,9-spirodifluorenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, dimethylethylsilyl, dimethyltert-butylsilyl, diethylmethylsilyl, tricyclopropanesilyl, tricyclobutanesilyl, triphenylsilyl, triphenylsilyl.

[0036] Most preferably, the compound of formula 1 is selected from any one of the following groups: .

[0037] The above lists some specific structural forms of the compounds shown in Formula 1 according to the present invention. However, the present invention is not limited to these chemical structures. Any structure based on Formula 1 with substituents as defined above should be included.

[0038] The following is one method for preparing the compound represented by Formula 1 of this invention, but the preparation method of this invention is not limited thereto. The core structure of the compound of Formula 1 can be prepared by the reaction route shown below, the substituents can be bonded by methods known in the art, and the type and position or number of substituents can be changed according to techniques known in the art.

[0039] [Synthesis Route]

[0040] Route 1: ; Route 2: ; Xa, Xb, Xc, Xd, and Xe are independently selected from Cl, Br, or I; The Qa is independently selected from Or B(OH)2; The M is independently selected from or .

[0041] The present invention provides an organic electroluminescent device, comprising an anode, an organic layer, and a cathode, wherein the organic layer is located between the anode and the cathode or outside at least one electrode of the cathode or the anode, and the organic layer comprises any one of the compounds described in the present invention.

[0042] Preferably, the organic layer of the organic light-emitting device can be formed as a single layer or as a multilayer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of the present invention can have a structure comprising one or more of the following as organic layers: a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, an electron transport layer, a hole blocking layer, an electron injection layer, and a charge generation layer. However, the structure of the organic light-emitting device described in this specification is not limited thereto, and may include fewer or more organic layers.

[0043] More preferably, the organic layer is located between the anode and the cathode, and the organic layer includes an electron transport layer, which comprises any one of the silicon-containing compounds.

[0044] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes a hole-blocking layer, which comprises any one of the silicon-containing compounds described in this invention.

[0045] Preferably, the organic layer is located between the anode and the cathode, and the organic layer includes an electron transport layer and a hole blocking layer, wherein the electron transport layer and the hole blocking layer simultaneously contain any one of the silicon-containing compounds described in this invention.

[0046] More preferably, the organic layer is located between the anode and the cathode, and the organic layer includes a light-emitting layer, which comprises any one of the silicon-containing compounds described in this invention.

[0047] More preferably, the organic layer includes a light-emitting layer, the light-emitting layer includes a host material, and the host material comprises any one of the silicon-containing compounds described in this invention.

[0048] More preferably, the light-emitting layer includes a host material, the host material comprising an N-type host material, and the N-type host material comprising any one of the silicon-containing compounds described in this invention.

[0049] Preferably, the organic layer is located outside at least one of the electrodes, the cathode or the anode, and the organic layer includes a light efficiency improvement layer, which comprises any one of the silicon-containing compounds described in this invention.

[0050] As the anode material of this invention, a material with a high work function is preferred in order to facilitate the injection of holes into the organic layer. For example, metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but not limited to these.

[0051] As the hole injection layer of the present invention, a material with good hole-accepting ability is preferred. Specific examples include, but are not limited to, metalloporphyrins, oligothiophenes, arylamines, hexanitrile hexaazabenzophenanthrene compounds, quinacridones, perylene compounds, etc.

[0052] As the hole transport layer of the present invention, a material with high hole mobility is preferred. Specific examples may include carbazole compounds, triaromatic amine compounds, benzidine compounds, fluorene compounds, phthalocyanine compounds, but are not limited thereto.

[0053] The material used as the light-emitting layer in this invention is a material that emits visible light by respectively receiving holes from the hole transport region and electrons from the electron transport region, and combining the received holes and electrons. The light-emitting layer may include a host material and a dopant material. As the host and guest materials of the light-emitting layer of the organic electroluminescent device of this invention, the host material may be one or a combination of two of anthracene derivatives, quinoxaline derivatives, triazine derivatives, xanthone derivatives, diphenyl ketone derivatives, carbazole derivatives, pyridine derivatives, or pyrimidine derivatives. Silicon-containing compounds are preferred. The guest material may be a pyrene derivative, a boron derivative, a chrysodium derivative, a spirofluorene derivative, an iridium complex, or a platinum complex.

[0054] The hole-blocking layer material of the present invention is a layer located on the light-emitting layer. Its function is to increase the hole-electron coupling probability by controlling electron mobility and preventing excessive hole movement, thereby improving the efficiency of the organic light-emitting device. The hole-blocking layer comprises a hole-blocking material, examples of which include compounds that introduce electron-withdrawing groups, preferably at least one of the silicon-containing compounds described in the present invention. Specific examples may include, but are not limited to, azazine derivatives (including triazine), triazole derivatives, oxadiazole derivatives, phenanthroline derivatives, and phosphine oxide derivatives. Silicon-containing compounds described in the present invention are preferred.

[0055] The electron transport material of this invention is a material used to receive electrons from an electron injection layer and transport the received electrons to a light-emitting layer. Preferably, the electron transport material is a material capable of easily receiving electrons from the cathode and transporting them to the light-emitting layer, and a material with high electron mobility. The aforementioned silicon-containing compounds can be used as electron transport layer materials. Examples of other electron transport materials include, but are not limited to: aluminum complexes of 8-hydroxyquinoline; Alq3-containing complexes; organic free radical compounds; hydroxyflavonoid metal complexes; and triazine derivatives. Alternatively, it can be used with, but is not limited to, fluorene, anthraquinone dimethyl, dibenzoquinone, thiaran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenemethylene, anthrone and its derivatives, metal complexes, or nitrogen-containing five-membered ring derivatives. The silicon-containing compounds described in this invention are preferred.

[0056] As the electron injection layer material of this invention, it can effectively inject electrons from the cathode into the organic layer, and a material with a low work function is preferred. Suitable materials include metals, alkali metals, alkaline earth metals, alkali metal halides, alkaline earth metal halides, alkali metal oxides, alkaline earth metal oxides, alkali metal salts, alkaline earth metal salts, rare earth metal oxides, rare earth metal halides, or metal complexes. Preferred materials include lithium, lithium fluoride, lithium oxide, lithium nitride, lithium 8-hydroxyquinoline, cesium, cesium carbonate, cesium 8-hydroxyquinoline, calcium, calcium fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, and magnesium oxide, but are not limited to these.

[0057] As the cathode of this invention, a transmission electrode, a semi-reflective electrode, or a reflective electrode can be selected, and a metal material with a low work function is generally preferred. When the cathode is a transmission electrode, the cathode material can be selected from transparent metal oxides such as indium tin oxide (ITO); when the cathode is a semi-reflective electrode or a reflective electrode, the cathode material can be selected from silver (Ag), magnesium (Mg), copper (Cu), aluminum (Al), platinum (Pt), palladium (Pd), gold (Au), nickel (Ni), lithium fluoride / calcium (LiF / Ca), lithium fluoride / aluminum (LiF / Al), molybdenum (Mo), or titanium (Ti), but is not limited to these.

[0058] As the capping layer described in this invention, a material with a high refractive index is preferred. This may include metal halides, oxides, nitrides, oxynitrides, sulfides, selenides, aromatic compounds, heteroaromatic compounds, aromatic amine compounds, etc., such as Alq3, NPD, CBP, LiF, CsF, MgF2, CaF2, CsCl, CuI, V2O5, WO3, MoO3, TiO2, ZrO, ZnO, SiO2, SiN, ZnS, etc., but is not limited thereto.

[0059] The organic layer, cathode, and anode of the aforementioned organic electroluminescent devices can be prepared by methods such as vacuum evaporation, sputtering, spin coating, spraying, screen printing, and laser transfer, but are not limited to these methods. When using vacuum deposition methods, the conditions for vacuum deposition vary depending on the compound.

[0060] The following embodiments further illustrate the technical solutions and effects of the present invention. However, the following embodiments are only for illustrating this specification, and the scope of this specification is not limited to these embodiments.

[0061] Description of raw materials, reagents, and characterization equipment: The present invention does not impose any particular restrictions on the source of raw materials used in the following embodiments, which can be commercially available products or prepared using preparation methods well known to those skilled in the art.

[0062] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent. Elemental analysis was performed using a VarioELcube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0063] Synthesis Examples

[0064] Synthesis Example 1: Synthesis of Compound 4

[0065] Preparation of intermediate A-4: Under nitrogen protection, a-4 (22.59 g, 100.00 mmol), b-4 (19.41 g, 100.00 mmol), K2CO3 (20.73 g, 150.00 mmol), Pd(PPh3)4 (1.16 g, 1.00 mmol), and 600 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol at a ratio of 10:1 to obtain intermediate A-4 (21.85 g, yield 74%) with an HPLC purity ≥99.85%. Mass spectrometry m / z: 294.0387 (theoretical value: 294.0398).

[0066] Preparation of intermediate B-4: Under nitrogen protection, A-4 (17.72 g, 60.00 mmol), pinacol diborate (30.47 g, 120.00 mmol), Na₂CO₃ (25.44 g, 240.00 mmol), Pd(dppf)Cl₂ (0.88 g, 1.20 mmol), and 500 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and then recrystallized from ethyl acetate to obtain intermediate B-4 (22.39 g, yield 78%); HPLC purity ≥ 99.89%. Mass spectrometry m / z: 478.2899 (theoretical value: 478.2882).

[0067] Preparation of compound 4: Under nitrogen protection, B-4 (9.57 g, 20.00 mmol), c-4 (10.71 g, 40.00 mmol), K2CO3 (8.29 g, 60.00 mmol), Pd(OAc)2 (0.09 g, 0.40 mmol), X-phos (0.19 g, 0.40 mmol), and 300 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5.5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from toluene to give compound 4 (10.61 g, yield 77%), HPLC purity ≥ 99.95%, mass spectrometry m / z: 688.2791 (theoretical value: 688.2771). Theoretical elemental content (%) C 45 H 36 N6Si: C, 78.46; H, 5.27; N, 12.20. Measured elemental content (%): C, 78.49; H, 5.29; N, 12.21.

[0068] Synthesis Example 2: Synthesis of Compound 14

[0069] Preparation of intermediate A-14: Under nitrogen protection, a-14 (63.47 g, 200.00 mmol), b-4 (38.82 g, 200.00 mmol), K2CO3 (41.46 g, 300.00 mmol), Pd(PPh3)4 (2.31 g, 2.00 mmol), and 1200 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5 hours. After the reaction was completed, the reactants were cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane (150 mL × 3 times). The organic phase was separated, dried over anhydrous magnesium sulfate, and the solvent was concentrated by rotary evaporation. The mixture was cooled to allow crystallization, filtered, and the resulting solid was recrystallized from toluene / ethanol (10:1) to obtain intermediate A-14 (51.64 g, yield 76%) with an HPLC purity ≥ 99.84%. Mass spectrometry m / z: 337.9878 (theoretical value: 337.9893).

[0070] Preparation of intermediate B-14: Under nitrogen protection, A-14 (50.96 g, 150.00 mmol), pinacol diborate (38.09 g, 150.00 mmol), Na₂CO₃ (31.80 g, 300.00 mmol), Pd(dppf)Cl₂ (1.10 g, 1.50 mmol), and 1000 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and then recrystallized from ethyl acetate to obtain intermediate B-14 (41.19 g, yield 71%); HPLC purity ≥ 99.81%. Mass spectrometry m / z: 386.1655 (theoretical value: 386.1640).

[0071] Preparation of intermediate C-14: Under nitrogen protection, B-14 (38.68 g, 100.00 mmol), C-4 (26.77 g, 100.00 mmol), K₂CO₃ (20.73 g, 150.00 mmol), Pd(PPh₃)₄ (1.16 g, 1.00 mmol), and 500 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol at a ratio of 10:1 to obtain intermediate C-14 (37.40 g, yield 76%) with an HPLC purity ≥ 99.83%. Mass spectrometry m / z: 491.1571 (theoretical value: 491.1585).

[0072] Preparation of intermediate D-14: Under nitrogen protection, C-14 (29.53 g, 60.00 mmol), pinacol diborate (15.24 g, 60.00 mmol), Na₂CO₃ (12.72 g, 120.00 mmol), Pd(dppf)Cl₂ (0.44 g, 0.60 mmol), and 400 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and then recrystallized from ethyl acetate to obtain intermediate D-14 (25.91 g, yield 74%); HPLC purity ≥ 99.85%. Mass spectrometry m / z: 583.2811 (theoretical value: 583.2826).

[0073] Preparation of compound 14: Under nitrogen protection, D-14 (11.67 g, 20.00 mmol), d-14 (6.88 g, 20.00 mmol), K2CO3 (4.15 g, 30.00 mmol), Pd(OAc)2 (0.04 g, 0.20 mmol), X-phos (0.10 g, 0.20 mmol), and 150 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5.5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from toluene to give compound 14 (11.48 g, yield 75%), HPLC purity ≥99.97%, mass spectrometry m / z: 764.3069 (theoretical value: 764.3084). Theoretical elemental content (%) C 51 H 40 N6Si: C, 80.07; H, 5.27; N, 10.99. Measured elemental content (%): C, 80.05; H, 5.26; N, 10.98.

[0074] Synthesis Example 3: Synthesis of Compound 57

[0075] Replacing a-14 with an equimolar amount of a-57 and d-14 with an equimolar amount of d-57, and following the same steps as in Synthesis Example 2, yielded compound 57 (11.77 g), with HPLC purity ≥ 99.96% and mass spectrometry m / z: 773.3666 (theoretical value: 773.3649). Theoretical elemental content (%) C 51 H 31 D9N6Si: C, 79.14; H, 6.38; N, 10.86. Measured elemental composition: C, 79.15; H, 6.39; N, 10.88.

[0076] Synthesis Example 4: Synthesis of Compound 69

[0077] Replacing a-14 with an equimolar amount of a-69 and d-14 with an equimolar amount of d-69, and following the same steps as in Synthesis Example 2, yielded compound 69 (12.43 g), with HPLC purity ≥ 99.93% and mass spectrometry m / z: 840.3387 (theoretical value: 840.3397). Theoretical elemental content (%) C 57 H 44 N6Si: C, 81.40; H, 5.27; N, 9.99. Measured elemental composition: C, 81.43; H, 5.28; N, 9.96.

[0078] Synthesis Example 5: Synthesis of Compound 95

[0079] Replacing a-14 with an equimolar amount of a-95 and d-14 with an equimolar amount of d-95, and following the same steps as in Synthesis Example 2, yielded compound 95 (13.74 g), with HPLC purity ≥ 99.91% and mass spectrometry m / z: 940.3717 (theoretical value: 940.3710). Theoretical elemental content (%) C 65 H 48 N6Si: C, 82.95; H, 5.14; N, 8.93. Measured elemental composition: C, 82.98; H, 5.16; N, 8.94.

[0080] Synthesis Example 6: Preparation of Compound 125

[0081] Replacing a-4 with an equimolar amount of a-125 and c-4 with an equimolar amount of c-125, and following the same steps as in Synthesis Example 1, yielded compound 125 (11.18 g), with HPLC purity ≥ 99.96% and mass spectrometry m / z: 744.3389 (theoretical value: 744.3397). Theoretical elemental content (%) C 49 H 44 N6Si: C, 79.00; H, 5.95; N, 11.28. Measured elemental composition: C, 79.02; H, 5.93; N, 11.27.

[0082] Synthesis Example 7: Preparation of Compound 147

[0083] Replacing a-14 with an equimolar amount of a-57, b-4 with an equimolar amount of b-147, and d-14 with an equimolar amount of d-147, while following the same steps as in Synthesis Example 2, yielded compound 147 (11.52 g), with an HPLC purity ≥ 99.97% and a mass spectrometry m / z of 788.3096 (theoretical value: 788.3084). Theoretical elemental content (%) C 53 H 40 N6Si: C, 80.68; H, 5.11; N, 10.65. Measured elemental composition: C, 80.67; H, 5.13; N, 10.67.

[0084] Synthesis Example 8: Synthesis of Compound 151

[0085] Replacing a-14 with an equimolar amount of a-151, b-4 with an equimolar amount of b-151, and d-14 with an equimolar amount of d-151, while following the same steps as in Synthesis Example 2, yielded compound 151 (12.23 g), with HPLC purity ≥ 99.95% and mass spectrometry m / z: 860.3466 (theoretical value: 860.3479). Theoretical elemental content (%) C 56 H 48 N6Si2: C, 78.10; H, 5.62; N, 9.76. Measured elemental composition: C, 78.13; H, 5.60; N, 9.75.

[0086] Synthesis Example 9: Synthesis of Compound 152

[0087] Replacing a-14 with an equimolar amount of a-151, c-4 with an equimolar amount of d-14, and d-14 with an equimolar amount of d-152, while following the same steps as in Synthesis Example 2, yielded compound 152 (13.54 g), with HPLC purity ≥ 99.99% and mass spectrometry m / z: 914.3569 (theoretical value 914.3553). Theoretical elemental content (%) C 63 H 46 N6Si: C, 82.68; H, 5.07; N, 9.18. Measured elemental composition: C, 82.67; H, 5.05; N, 9.19.

[0088] Synthesis Example 10: Synthesis of Compound 155

[0089] Replacing a-14 with an equimolar amount of a-155, b-4 with an equimolar amount of b-155, and d-14 with an equimolar amount of d-155, while following the same steps as in Synthesis Example 2, yielded compound 155 (12.65 g), with HPLC purity ≥ 99.94% and mass spectrometry m / z: 890.3545 (theoretical value 890.3553). Theoretical elemental content (%) C 61 H 46 N6Si: C, 82.21; H, 5.20; N, 9.43. Measured elemental composition: C, 82.23; H, 5.22; N, 9.44.

[0090] Synthesis Example 11: Synthesis of Compound 236

[0091] Replacing a-4 with an equimolar amount of a-236 and c-4 with an equimolar amount of c-236, and following the same steps as in Synthesis Example 1, yielded compound 236 (12.31 g), with HPLC purity ≥ 99.96% and mass spectrometry m / z: 788.3072 (theoretical value: 788.3084). Theoretical elemental content (%) C 53 H 40 N6Si: C, 80.68; H, 5.11; N, 10.65. Measured elemental content: C, 80.67; H, 5.14; N, 10.66.

[0092] Synthesis Example 12: Synthesis of Compound 305

[0093] Replacing a-4 with an equimolar amount of a-236 and c-4 with an equimolar amount of c-305, and following the same steps as in Synthesis Example 1, yielded compound 305 (10.92 g), with HPLC purity ≥ 99.90% and mass spectrometry m / z: 768.3381 (theoretical value: 768.3397). Theoretical elemental content (%) C 51 H 44 N6Si: C, 79.65; H, 5.77; N, 10.93. Measured elemental composition: C, 79.62; H, 5.75; N, 10.94.

[0094] Synthesis Example 13: Synthesis of Compound 307

[0095] Replacing c-4 with an equimolar amount of d-14, and d-14 with an equimolar amount of d-304, while following the same steps as in Synthesis Example 2, yielded compound 307 (13.04 g), with HPLC purity ≥ 99.94% and mass spectrometry m / z: 880.3727 (theoretical value 880.3710). Theoretical elemental content (%) C 60 H 48 N6Si: C, 81.78; H, 5.49; N, 9.54. Measured elemental composition: C, 81.77; H, 5.47; N, 9.55.

[0096] Synthesis Example 14: Synthesis of Compound 309

[0097] Replacing a-14 with an equimolar amount of a-69, c-4 with an equimolar amount of c-309, and d-14 with an equimolar amount of d-309, while following the same steps as in Synthesis Example 2, yielded compound 309 (14.83 g), with an HPLC purity ≥ 99.92% and a mass spectrometry m / z of 1058.4477 (theoretical value 1058.4492). Theoretical elemental content (%) C 74 H 58 N6Si: C, 83.90; H, 5.52; N, 7.93. Measured elemental composition: C, 83.91; H, 5.54; N, 7.94.

[0098] Synthesis Example 15: Preparation of Compound 333

[0099] Replacing c-4 with an equimolar amount of c-333 and d-14 with an equimolar amount of d-333, and following the same steps as in Synthesis Example 2, yielded compound 333 (15.09 g), with HPLC purity ≥ 99.97% and mass spectrometry m / z: 1032.5290 (theoretical value 1032.5275). Theoretical elemental content (%) C 71 H 68 N6Si: C, 82.52; H, 6.63; N, 8.13. Measured elemental composition: C, 82.50; H, 6.64; N, 8.11.

[0100] Synthesis Example 16: Synthesis of Compound 326

[0101] Replacing c-4 with an equimolar amount of c-326, and following the same steps as in Synthesis Example 1, yielded compound 326 (10.55 g), with HPLC purity ≥ 99.98% and mass spectrometry m / z: 722.3476 (theoretical value: 722.3460). Theoretical elemental content (%) C 47 H 34 D6N6Si: C, 78.08; H, 6.41; N, 11.62. Measured elemental composition: C, 78.06; H, 6.40; N, 11.61.

[0102] Synthesis Example 17: Synthesis of Compound 368

[0103] Replacing b-4 with an equimolar amount of b-368, and following the same steps as in Synthesis Example 1, yielded compound 368 (11.48 g), with HPLC purity ≥ 99.94% and mass spectrometry m / z: 764.3070 (theoretical value: 764.3084). Theoretical elemental content (%) C 51 H 40 N6Si: C, 80.07; H, 5.27; N, 10.99. Measured elemental composition: C, 80.05; H, 5.25; N, 10.97.

[0104] Synthesis Example 18: Synthesis of Compound 389

[0105]

[0106] Preparation of intermediate H-389: Under nitrogen protection, g-389 (77.64 g, 400.00 mmol), h-389 (76.98 g, 400.00 mmol), K2CO3 (110.56 g, 800.00 mmol), Pd(PPh3)4 (4.62 g, 4.00 mmol), and 2000 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from the solid using toluene / ethanol at a ratio of 10:1 to obtain intermediate H-389 (82.74 g, yield 79%) with an HPLC purity ≥99.88%. Mass spectrometry m / z: 261.0749 (theoretical value: 261.0741).

[0107] Preparation of intermediate b-389: Under nitrogen protection, H-389 (78.55 g, 300.00 mmol), pinacol diboronate (76.18 g, 300.00 mmol), Na2CO3 (63.59 g, 600.00 mmol), Pd(dppf)Cl2 (2.20 g, 3.00 mmol), and 2000 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and then recrystallized from ethyl acetate to obtain intermediate b-389 (76.32 g, yield 72%); HPLC purity ≥ 99.83%. Mass spectrometry m / z: 353.1999 (theoretical value: 353.1982).

[0108] Preparation of compound 389: Replace a-14 with an equimolar amount of a-57, b-4 with an equimolar amount of b-389, and d-14 with an equimolar amount of d-389. The remaining steps are the same as in Synthesis Example 2. This yields compound 389 (13.20 g), with an HPLC purity ≥ 99.92% and a mass spectrometry m / z of 891.3516 (theoretical value 891.3506). Theoretical elemental content (%) C 60 H 45 N7Si: C, 80.78; H, 5.08; N, 10.99. Measured elemental composition: C, 80.79; H, 5.06; N, 10.94.

[0109] Synthesis Example 19: Synthesis of Compound 463

[0110] Replacing a-14 with an equimolar amount of a-57, c-4 with an equimolar amount of c-463, and d-14 with an equimolar amount of c-4, while following the same steps as in Synthesis Example 2, yielded compound 463 (11.32 g), with an HPLC purity ≥ 99.94% and a mass spectrometry m / z of 764.3071 (theoretical value 764.3084). Theoretical elemental content (%) C 51 H 40 N6Si: C, 80.07; H, 5.27; N, 10.99. Measured elemental composition: C, 80.05; H, 5.25; N, 10.96.

[0111] Synthesis Example 20: Synthesis of Compound 470

[0112] Replacing a-14 with an equimolar amount of a-69, c-4 with an equimolar amount of c-470, and d-14 with an equimolar amount of c-4, while following the same steps as in Synthesis Example 2, yielded compound 470 (11.48 g). HPLC purity ≥ 99.97%, mass spectrometry m / z: 764.3098 (theoretical value 764.3084). Theoretical elemental content (%) C 51 H 40 N6Si: C, 80.07; H, 5.27; N, 10.99. Measured elemental composition: C, 80.06; H, 5.28; N, 10.94.

[0113] Synthesis Example 21: Synthesis of Compound 497

[0114] Replacing a-14 with an equimolar amount of a-57, c-4 with an equimolar amount of c-470, and d-14 with an equimolar amount of d-497, while following the same steps as in Synthesis Example 2, yielded compound 497 (11.16 g), with an HPLC purity ≥ 99.91% and a mass spectrometry m / z of 774.3721 (theoretical value 774.3711). Theoretical elemental content (%) C 51 H 30 D 10 N6Si: C, 79.03; H, 6.50; N, 10.84. Measured elemental content: C, 79.05; H, 6.51; N, 10.86.

[0115] Synthesis Example 22: Synthesis of Compound 532

[0116] Replacing a-14 with an equimolar amount of a-155, c-4 with an equimolar amount of c-532, and d-14 with an equimolar amount of d-532, while following the same steps as in Synthesis Example 2, yielded compound 532 (12.28 g), with an HPLC purity ≥ 99.96% and a mass spectrometry m / z of 840.3382 (theoretical value 840.3397). Theoretical elemental content (%) C 57 H 44 N6Si: C, 81.40; H, 5.27; N, 9.99. Measured elemental composition: C, 81.41; H, 5.25; N, 9.97.

[0117] Synthesis Example 23: Synthesis of Compound 565

[0118] Replacing a-14 with an equimolar amount of a-57, c-4 with an equimolar amount of c-470, and d-14 with an equimolar amount of d-565, while following the same steps as in Synthesis Example 2, yielded compound 565 (12.55 g), with HPLC purity ≥ 99.90% and mass spectrometry m / z: 814.3252 (theoretical value 814.3240). Theoretical elemental content (%) C 55 H 42 N6Si: C, 81.05; H, 5.19; N, 10.31. Measured elemental content: C, 81.04; H, 5.17; N, 10.30.

[0119] Synthesis Example 24: Synthesis of Compound 579:

[0120] Replacing a-14 with an equimolar amount of a-69, c-4 with an equimolar amount of c-579, and d-14 with an equimolar amount of d-579, while following the same steps as in Synthesis Example 2, yielded compound 579 (11.66 g), with an HPLC purity ≥ 99.94% and a mass spectrometry m / z of 820.3701 (theoretical value 820.3710). Theoretical elemental content (%) C 55 H 48 N6Si: C, 80.45; H, 5.89; N, 10.24. Measured elemental composition: C, 80.44; H, 5.86; N, 10.25.

[0121] Synthesis Example 25: Synthesis of Compound 582

[0122] Replacing a-14 with an equimolar amount of a-151, c-4 with an equimolar amount of c-470, and d-14 with an equimolar amount of d-582, while following the same steps as in Synthesis Example 2, yielded compound 582 (13.28 g), with an HPLC purity ≥ 99.93% and a mass spectrometry m / z of 908.3861 (theoretical value 908.3874). Theoretical elemental content (%) C 57 H 56 N6Si3: C, 75.29; H, 6.21; N, 9.24. Measured elemental composition: C, 75.27; H, 6.20; N, 9.23.

[0123] Synthesis Example 26: Synthesis of Compound 659:

[0124]

[0125] Preparation of intermediate J-659: Under nitrogen protection, J-659 (16.05 g, 60.00 mmol), pinacol diborate (15.24 g, 60.00 mmol), Na₂CO₃ (12.72 g, 120.00 mmol), Pd(dppf)Cl₂ (0.44 g, 0.60 mmol), and 400 mL of 1,4-dioxane were added to a reaction flask. The mixture was stirred under reflux for 6 hours. After the reaction was completed, the mixture was cooled to room temperature, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and then recrystallized from ethyl acetate to obtain intermediate J-659 (14.16 g, yield 75%); HPLC purity ≥ 99.84%. Mass spectrometry m / z: 314.1253 (theoretical value: 314.1245).

[0126] Preparation of intermediate d-659: Under nitrogen protection, J-659 (12.58 g, 40.00 mmol), p-689 (15.21 g, 40.00 mmol), K2CO3 (8.29 g, 60.00 mmol), Pd(OAc)2 (0.09 g, 0.40 mmol), X-phos (0.19 g, 0.40 mmol), and 300 mL of toluene / ethanol / water (2:1:1) were added to a reaction flask. The mixture was stirred under reflux for 5.5 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, filtered, washed with distilled water, and then recrystallized from toluene to obtain intermediate d-659 (13.86 g, yield 71%), with HPLC purity ≥99.81% and mass spectrometry m / z: 487.1054 (theoretical value: 487.1063).

[0127] Preparation of compound 659: Replace a-14 with an equimolar amount of a-155 and d-14 with an equimolar amount of d-659, following the same steps as in Example 2. This yielded compound 659 (13.09 g), with an HPLC purity ≥ 99.95% and a mass spectrometry m / z of 908.3288 (theoretical value 908.3271). Theoretical elemental content (%) C 58 H 43 F3N6Si: C, 76.63; H, 4.77; N, 9.24. Measured elemental composition: C, 76.62; H, 4.78; N, 9.25.

[0128] Synthesis Example 27: Synthesis of Compound 589

[0129] Replacing c-4 with an equimolar amount of d-14, and d-14 with an equimolar amount of d-589, while following the same steps as in Synthesis Example 2, yielded compound 589 (14.11 g), with an HPLC purity ≥ 99.97% and a mass spectrometry m / z of 916.3728 (theoretical value 916.3710). Theoretical elemental content (%) C 63 H 48 N6Si: C, 82.50; H, 5.28; N, 9.16. Measured elemental composition: C, 82.51; H, 5.27; N, 9.18.

[0130] Synthesis Example 28: Synthesis of Compound 688

[0131] Replacing c-4 with an equimolar amount of c-688, and following the same steps as in Synthesis Example 1, yielded compound 688 (12.62 g), with HPLC purity ≥ 99.92% and mass spectrometry m / z: 840.3381 (theoretical value: 840.3397). Theoretical elemental content (%) C 57 H 44 N6Si: C, 81.40; H, 5.27; N, 9.99. Measured elemental composition: C, 81.41; H, 5.24; N, 9.98.

[0132] Synthesis Example 29: Synthesis of Compound 786

[0133] Replacing a-14 with an equimolar amount of a-57 and d-14 with an equimolar amount of d-786, and following the same steps as in Synthesis Example 2, yielded compound 786 (11.07 g), with HPLC purity ≥ 99.91% and mass spectrometry m / z: 768.3351 (theoretical value 768.3335). Theoretical elemental content (%) C 51 H 36 D4N6Si: C, 79.65; H, 5.77; N, 10.93. Measured elemental composition: C, 79.64; H, 5.79; N, 10.91.

[0134] Synthesis Example 30: Synthesis of Compound 696

[0135] Replacing a-4 with an equimolar amount of a-696 and c-4 with an equimolar amount of c-688, and following the same steps as in Synthesis Example 1, yielded compound 696 (13.29 g), with HPLC purity ≥ 99.95% and mass spectrometry m / z: 840.3389 (theoretical value: 840.3397). Theoretical elemental content (%) C 57 H 44 N6Si: C, 81.40; H, 5.27; N, 9.99. Measured elemental composition: C, 81.44; H, 5.29; N, 9.96.

[0136] Synthesis Example 31: Synthesis of Compound 754

[0137] Replacing a-14 with an equimolar amount of a-57, c-4 with an equimolar amount of c-754, and d-14 with an equimolar amount of d-754, while following the same steps as in Synthesis Example 2, yielded compound 754 (13.92 g), with HPLC purity ≥ 99.99% and mass spectrometry m / z: 952.4658 (theoretical value 952.4649). Theoretical elemental content (%) C 65 H 60 N6Si: C, 81.89; H, 6.34; N, 8.82. Measured elemental content: C, 81.87; H, 6.33; N, 8.80.

[0138] Synthesis Example 32: Synthesis of Compound 788

[0139] Replacing a-14 with an equimolar amount of a-57 and d-14 with an equimolar amount of d-788, and following the same steps as in Synthesis Example 2, yielded compound 788 (11.34 g), with HPLC purity ≥ 99.92% and mass spectrometry m / z: 765.3021 (theoretical value 765.3036). Theoretical elemental content (%) C 50 H 39 N7Si: C, 78.40; H, 5.13; N, 12.80. Measured elemental composition: C, 78.43; H, 5.14; N, 12.82.

[0140] Synthesis Example 33: Synthesis of Compound 790

[0141] Replacing a-14 with an equimolar amount of a-151 and d-14 with an equimolar amount of d-790, and following the same steps as in Synthesis Example 2, yielded compound 790 (13.45 g), with HPLC purity ≥ 99.93% and mass spectrometry m / z: 814.3225 (theoretical value 814.3240). Theoretical elemental content (%) C 55 H 42 N6Si: C, 81.05; H, 5.19; N, 10.31. Measured elemental content: C, 81.03; H, 5.17; N, 10.34.

[0142] Synthesis Example 34: Synthesis of Compound 807

[0143] Replacing a-14 with an equimolar amount of a-155 and d-14 with an equimolar amount of d-807, and following the same steps as in Synthesis Example 2, yielded compound 807 (12.94 g), with HPLC purity ≥ 99.96% and mass spectrometry m / z: 818.3571 (theoretical value 818.3553). Theoretical elemental content (%) C 55 H 46 N6Si: C, 80.65; H, 5.66; N, 10.26. Measured elemental composition: C, 80.66; H, 5.67; N, 10.28.

[0144] Synthesis Example 35: Synthesis of Compound 810

[0145] Replacing a-14 with an equimolar amount of a-57 and d-14 with an equimolar amount of d-810, and following the same steps as in Synthesis Example 2, yielded compound 810 (13.75 g), with HPLC purity ≥ 99.92% and mass spectrometry m / z: 880.3722 (theoretical value 880.3710). Theoretical elemental content (%) C 60 H 48 N6Si: C, 81.78; H, 5.49; N, 9.54. Measured elemental composition: C, 81.73; H, 5.48; N, 9.56.

[0146] Synthesis Example 36: Synthesis of Compound 862

[0147] Replacing a-4 with an equimolar amount of a-862, b-4 with an equimolar amount of b-862, and c-4 with an equimolar amount of c-862, while following the same steps as in Synthesis Example 1, yielded compound 862 (10.74 g), with HPLC purity ≥ 99.99% and mass spectrometry m / z: 715.4475 (theoretical value: 715.4465). Theoretical elemental content (%) C 45 H9D 27 N6Si: C, 75.48; H, 8.86; N, 11.74. Measured elemental composition: C, 75.47; H, 8.89; N, 11.77.

[0148] Synthesis Example 37: Synthesis of Compound 908

[0149] Replacing a-4 with an equimolar amount of a-908 and b-4 with an equimolar amount of b-908, while following the same steps as in Synthesis Example 1, yielded compound 908 (12.27 g), with HPLC purity ≥ 99.98% and mass spectrometry m / z: 806.3566 (theoretical value: 806.3553). Theoretical elemental content (%) C 54 H 46 N6Si: C, 80.36; H, 5.75; N, 10.41. Measured elemental composition: C, 80.37; H, 5.74; N, 10.46.

[0150] Synthesis Example 38: Synthesis of Compound 1071

[0151] Replacing a-14 with an equimolar amount of a-57, c-4 with an equimolar amount of c-1071, and d-14 with an equimolar amount of d-1071, while following the same steps as in Synthesis Example 2, yielded compound 1071 (14.27 g), with an HPLC purity ≥ 99.92% and a mass spectrometry m / z of 963.3769 (theoretical value 963.3757). Theoretical elemental content (%) C 68 H 49 N5Si: C, 84.70; H, 5.12; N, 7.26. Measured elemental composition: C, 84.72; H, 5.14; N, 7.24.

[0152] Synthesis Example 39: Synthesis of Compound 1085

[0153] Replacing a-14 with an equimolar amount of a-151, b-4 with an equimolar amount of b-1085, and d-14 with an equimolar amount of d-1085, while following the same steps as in Synthesis Example 2, yielded compound 1085 (10.04 g), with an HPLC purity ≥ 99.96% and a mass spectrometry m / z of 687.2801 (theoretical value 687.2818). Theoretical elemental content (%) C 46 H 37 N5Si: C, 80.32; H, 5.42; N, 10.18. Measured elemental composition: C, 80.34; H, 5.44; N, 10.16.

[0154] Synthesis Example 40: Synthesis of Compound 1146

[0155] Replacing a-14 with an equimolar amount of a-151, c-4 with an equimolar amount of c-1146, and d-14 with an equimolar amount of d-1085, while following the same steps as in Synthesis Example 2, yielded compound 1146 (11.29 g), with HPLC purity ≥ 99.91% and mass spectrometry m / z: 762.3186 (theoretical value 762.3179). Theoretical elemental content (%) C 53 H 42 N4Si: C, 83.43; H, 5.55; N, 7.34. Measured elemental composition: C, 83.42; H, 5.56; N, 7.38.

[0156] Synthesis Example 41: Synthesis of Compound 1186

[0157] Replacing a-4 with an equimolar amount of a-1186 and c-4 with an equimolar amount of c-1186, and following the same steps as in Synthesis Example 1, yielded compound 1186 (10.85 g), with HPLC purity ≥ 99.93% and mass spectrometry m / z: 686.2847 (theoretical value: 686.2866). Theoretical elemental content (%) C 47 H 38 N4Si: C, 82.18; H, 5.58; N, 8.16. Measured elemental composition: C, 82.19; H, 5.57; N, 8.18.

[0158] Synthesis Example 42: Synthesis of Compound 1203

[0159] Replacing a-14 with an equimolar amount of a-151, b-4 with an equimolar amount of b-1203, c-4 with an equimolar amount of c-470, and d-14 with an equimolar amount of c-4, while following the same steps as in Synthesis Example 2, yielded compound 1203 (12.28 g), with an HPLC purity ≥ 99.98% and a mass spectrometry m / z of 840.3388 (theoretical value 840.3397). Theoretical elemental content (%) C 57 H 44 N6Si: C, 81.40; H, 5.27; N, 9.99. Measured elemental composition: C, 81.45; H, 5.26; N, 9.98.

[0160] Device Examples

[0161] Test conditions: A combined IVL test system was constructed using test software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter to test the driving voltage and luminous efficiency of organic electroluminescent devices (OLEDs). The lifetime of the OLEDs was tested using the McScience M6000 OLED lifetime testing system.

[0162] The test environment was atmospheric, and the temperature was room temperature; at 10 mA / cm 2 The driving voltage, luminous efficiency, and the time required for the brightness to decrease to 95% of the initial brightness (T95) were measured at the current density.

[0163] Test preparation: The ITO (100nm) glass substrate was washed twice with distilled water and ultrasonically cleaned for 30 minutes. It was then washed twice more with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water cleaning was completed, it was ultrasonically cleaned in sequence with isopropanol, acetone and methanol solvents. After drying on a hot plate heated to 120°C, the dried substrate was transferred to a plasma cleaner and cleaned for 5 minutes.

[0164] The functional layer compounds required for fabricating organic electroluminescent devices are shown below:

[0165] Device Example 1: Fabrication of a Red Organic Electroluminescent Device

[0166] The cleaned ITO substrate is transferred to an evaporation machine. A 10 nm thick layer of HI-1 and HT-1 is deposited on the ITO substrate as a hole injection layer (HI-1 to HT-1 mass ratio of 1:99). A 120 nm thick layer of HT-1 is then deposited on the hole injection layer as a hole transport layer. A 20 nm thick light-emitting layer is then vacuum-deposited on the hole transport layer. The light-emitting layer contains RH-1 as the host material and RD-1 as the dopant material (RH-1 to RD-1 mass ratio of 98:2). Then, a 30 nm thick layer of the present invention's compound 4 and Liq is vacuum-deposited on the light-emitting layer as an electron transport layer (compound 4 to Liq mass ratio of 1:1). A 1 nm thick layer of LiF is then deposited on the electron transport layer as an electron injection layer. Finally, a 100 nm thick layer of Al is deposited on the electron injection layer as a cathode, thereby fabricating an organic electroluminescent device.

[0167] Device Examples 2-42: Fabrication of Red Organic Electroluminescent Devices

[0168] Organic electroluminescent devices were prepared using the same preparation method as in Device Example 1, replacing compound 4 in Device Example 1 with compounds from Table 1 as electron transport layer materials.

[0169] Comparative Examples 1 to 4: Organic electroluminescent devices were prepared by replacing compound 4 in device example 1 with Ref-1, Ref-2, Ref-3, and Ref-4 as electron transport layer materials, using the same preparation method as in device example 1.

[0170] Table 1: Test results of luminescence characteristics of organic electroluminescent devices 1-42 and comparative examples 1-4

[0171]

[0172] As can be seen from the data in Table 1, the silicon-containing compound described in this invention has a high electron mobility, which can improve electron transport capability, thereby improving the luminous efficiency and lifespan of organic electroluminescent devices and reducing the driving voltage of the devices.

[0173] The functional layer compounds required for fabricating organic electroluminescent devices are shown below:

[0174] Device Example 43: Fabrication of a Blue Organic Electroluminescent Device

[0175] The cleaned ITO substrate is transferred to an evaporation machine. A 10 nm thick layer of HI-2 and HT-2 is deposited on the ITO substrate as a hole injection layer (HI-2 to HT-2 mass ratio 1:99). A 120 nm thick layer of HT-2 is then deposited on the hole injection layer as a hole transport layer. A 20 nm thick light-emitting layer is then vacuum-deposited on the hole transport layer. The light-emitting layer contains BH-1 as the host material and BD-1 as the dopant material (BH-1 to BD-1 mass ratio 99:1). A 5 nm thick layer of the compound of this invention is then vacuum-deposited on the light-emitting layer as a hole blocking layer. A 30 nm thick layer of ET-1 and Liq is then deposited on the hole blocking layer as an electron transport layer (ET-1 to Liq mass ratio 1:1). A 1 nm thick layer of LiF is then deposited on the electron transport layer as an electron injection layer. Finally, a 100 nm thick layer of Al is deposited on the electron injection layer as a cathode, thereby fabricating an organic electroluminescent device.

[0176] Device Examples 44-84: Fabrication of Blue Organic Electroluminescent Devices

[0177] Organic electroluminescent devices were prepared by replacing compound 4 in device example 43 with compounds from Table 2 as hole blocking layer materials, using the same method as device example 42.

[0178] Comparative Examples 5 to 6: Organic electroluminescent devices were prepared by replacing compound 4 in device example 43 with Ref-5 and Ref-6 as hole blocking layer materials, using the same method as device example 42.

[0179] Table 2: Test results of luminescence characteristics of organic electroluminescent devices 43-84 and comparative examples 5-6

[0180]

[0181] As can be seen from the data in Table 2, when the silicon-containing compound described in this invention is applied to the hole blocking layer of an organic electroluminescent device, compared with comparative compounds Ref-5 to Ref-6, the device has higher luminous efficiency, longer lifespan, and lower driving voltage. The compound of this invention is a hole blocking layer material with good performance.

[0182] It should be noted that the present invention has been specifically described with reference to individual embodiments, but those skilled in the art can make various forms or details of improvements to the present invention without departing from the principles of the present invention, and these improvements also fall within the protection scope of the present invention.

Claims

1. A silicon-containing compound, characterized in that, The silicon-containing compound is shown in Formula 1: ； in, The x is independently selected from C(R2) or N, and at least two x are N; The z is independently selected from C(R3) or N, and at least two z are N; The Ara, Arb, Arc, and Ard are independently selected from any one of substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C6-C30 aromatic rings, and C3-C15 alicyclic fused cycloalloys. Furthermore, the "substituted or unsubstituted..." groups of Ara, Arb, Arc, and Ard are selected from any one of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, fused cycloalkanes of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings; L1 and L2 are each independently selected from any one of single-bonded, substituted or unsubstituted C6-C30 arylene, or substituted or unsubstituted C2-C30 heteroarylene. The L3 is selected from any one of substituted or unsubstituted C6-C30 arylene or substituted or unsubstituted C2-C30 heteroarylene; The R0 is independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl; The n is selected from 1, 2, or 3; R1, R2, and R3 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted C6-C30 aromatic ring, and fused cycloalkanes of C3-C15 alicyclic rings; The La, Lb, Lc, and Ld are independently selected from single bonds, any one of the following groups, or a combination thereof: ； The value of k is selected from 1, 2, 3, or 4; The u is independently selected from C(R) 12 ) or N; The U is selected from C(R) 13 R 14 ) or N(R 15 ); The ring A is selected from substituted or unsubstituted C3-C15 alicyclic rings; X3 is selected from O, S, or N(R) 16 ); Q1 is selected from C(R) 17 ) or N; The R 11 R 12 Independently selected from any one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcohols of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings, or two adjacent R groups. 12 The links form substituted or unsubstituted rings; The R 13 R 14 Independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcohols of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings, or R 13 R 14 The links form substituted or unsubstituted rings; The R 15 R 16 R 17 The independent group is selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C15 alicyclic fused cycloalcohol.

2. The silicon-containing compound according to claim 1, characterized in that, The silicon-containing compound is selected from one of the following formulas 1-1 to 1-6: ； The R0 is independently selected from hydrogen, deuterium, substituted or unsubstituted groups of any one of the following: methyl, ethyl, n-propyl, n-butyl, isopropyl, sec-butyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, undecyl, dodecyl, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclohexyl, cyclooctyl, norbornyl, adamantyl; R1, L1, L2, L3, La, Lb, Lc, Ld, Ara, Arb, Arc, Ard, and n are the same as those in Equation 1.

3. The silicon-containing compound according to claim 1, characterized in that, The Ara, Arb, Arc, and Ard are independently selected from any one of the following groups: ； The Ra and Rb are independently selected from any one of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C15 alicyclic fused cycloalkanes, or two adjacent Ra are connected to form a substituted or unsubstituted ring; The Ry and Rt are independently selected from any one of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, or Rt and Ry are connected to form a substituted or unsubstituted ring. The Rw is independently selected from any one of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C15 alicyclic fused cycloalcohol, or two adjacent Rws connected to form a substituted or unsubstituted ring; The a1 is independently selected from 1, 2, 3, 4 or 5; the a2 is independently selected from 1, 2, 3 or 4; the a3 is independently selected from 1, 2 or 3; the a4 is independently selected from 1 or 2; the a5 is independently selected from 1, 2, 3, 4, 5 or 6; the a6 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8; the a7 is independently selected from 1, 2, 3, 4, 5, 6 or 7; and the a8 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

4. The silicon-containing compound according to claim 1, characterized in that, The L1 and L2 are independently selected from single bonds, any one of the following groups, or a combination thereof: ； The q is selected from 1, 2, 3, or 4; The m is independently selected from C (Rc) or N; The V is selected from O, S, C (ReRf) or N (Rh); Z1 is independently selected from O, S, or N (Ri); The Rc and Rd are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcohols of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings, or adjacent Rc are connected to form a substituted or unsubstituted ring; The Re and Rf are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcohols of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings, or Re and Rf are connected to form substituted or unsubstituted rings; The Rh and Ri are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C15 alicyclic fused cycloyl group; The c1 is independently selected from 1 or 2, the c2 is independently selected from 1, 2, 3 or 4, the c3 is independently selected from 1, 2, 3, 4, 5 or 6, and the c4 is independently selected from 1, 2, 3, 4, 5, 6, 7 or 8.

5. The silicon-containing compound according to claim 1, characterized in that, The L3 is selected from any one or a combination of the following groups: ； The v is independently selected from C(R5) or N; The A is selected from O, S, C (R6R7) or N (R8); The ring B is selected from substituted or unsubstituted C3-C15 alicyclic rings; Q2 is selected from C(R) 20 ) or N; X2 is selected from O, S or N (R9); The R5 and R4 are independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcohols of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings, or two adjacent R5s are connected to form a substituted or unsubstituted ring; The R6, R7, R 20 Independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C15 alicyclic fused cycloalcohol, or R6 and R7 linked to form a substituted or unsubstituted ring; R8 and R9 are independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C15 alicyclic fused cycloalcohol.

6. The silicon-containing compound according to claim 1, characterized in that, The La, Lb, Lc, and Ld are independently selected from single bonds, any one of the following groups, or a combination thereof: ； The R 11 R 12 Independently selected from any one of the following: hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, fused cycloalcohols of substituted or unsubstituted C6-C30 aromatic rings and C3-C15 alicyclic rings, or two adjacent R groups. 12 The links form substituted or unsubstituted rings; The R 13 '、R 14 'Independently selected from any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted silyl, or R 13 '、R 14 'Connecting to form substituted or unsubstituted rings; The R 15 R 15 'Independently selected from any one of hydrogen, deuterium, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl, substituted or unsubstituted silyl, substituted or unsubstituted C6-C30 aromatic ring and C3-C15 alicyclic fused cycloalcoholic group; The number e1 is independently selected from 1, 2, 3, or 4; the number e2 is independently selected from 1, 2, or 3; the number e3 is independently selected from 1, 2, 3, 4, or 5; the number e4 is independently selected from 1 or 2; the number e5 is independently selected from 1, 2, 3, 4, 5, or 6; the number e6 is independently selected from 1, 2, 3, 4, 5, 6, 7, or 8; and the number e7 is independently selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.

7. The silicon-containing compound according to claim 1, characterized in that, The compound of Formula 1 is selected from any one of the following groups: 。 8. An organic electroluminescent device, comprising an anode, an organic layer, and a cathode, characterized in that, The organic layer is located between the anode and the cathode or outside at least one of the electrodes, the cathode or the anode, and the organic layer comprises any one of the silicon-containing compounds according to claims 1 to 7.

9. The organic electroluminescent device according to claim 8, characterized in that, The organic layer is located between the anode and the cathode, and the organic layer includes an electron transport layer, which comprises any one of the silicon-containing compounds according to claims 1 to 7.

10. The organic electroluminescent device according to claim 8, characterized in that, The organic layer is located between the anode and the cathode, and the organic layer includes a hole-blocking layer comprising any one of the silicon-containing compounds according to claims 1 to 7.

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