Star-shaped triamine compound and organic light emitting device thereof

Abstract

The application provides a star-shaped triamine compound and an organic light-emitting device, and relates to the technical field of organic photoelectric materials.The compound takes benzene as a center, connects three triarylamines, and at least connects one dibenzo five-membered ring on the triarylamine; meanwhile, at least one substituted or unsubstituted silyl group is contained in the structure of formula I, the solubility is enhanced, film formation is facilitated, good film formation and thermal stability are achieved; on the other hand, the compound has good hole mobility, appropriate HOMO energy level and T1 value, and is applied to the organic light-emitting device, especially as a hole transport layer material and a cover layer material, so that the light-emitting efficiency of the device can be effectively improved, and the service life of the device is prolonged.The compound can be widely applied to the fields of panel display, lighting source, flexible OLED, organic solar cell, organic photoreceptor, indicator, signal lamp and the like.

Description

Technical Field

[0001] This invention relates to the field of organic optoelectronic materials technology, and in particular to a star-shaped triamine compound and its organic light-emitting device. Background Technology

[0002] Materials used as organic layers in organic light-emitting devices (OLEDs) can be broadly categorized by function into luminescent materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials, and capping materials. Luminescent materials can be classified by their light-emitting mechanism into fluorescent materials and phosphorescent materials, and also by their emission color into blue, green, and red luminescent materials. The light-emitting principle of OLEDs is as follows: when a voltage is applied between the anode and cathode, holes injected from the anode move to the luminescent layer via the hole transport layer, while electrons injected from the cathode move to the luminescent layer via the electron transport layer. The holes and electrons recombine in the luminescent layer to generate excitons. Light is generated during the transition of these excitons from the excited state to the ground state.

[0003] The efficiency of organic light-emitting devices (OLEDs) can generally be divided into internal luminous efficiency and external luminous efficiency. Internal luminous efficiency is related to the efficiency of exciton generation and light conversion in the organic layers between the cathode and anode, such as hole transport layers, emitting layers, and electron transport layers. Theoretically, the internal luminous efficiency of fluorescence is 25%, while that of phosphorescence is 100%. External luminous efficiency refers to the efficiency of light generated in the organic layers being extracted to the outside of the OLED. To prevent the loss of light due to total internal reflection, organic compounds are typically used as a capping layer.

[0004] Currently, the types of hole and electron transport materials used in organic light-emitting devices (OLEDs) are relatively limited, leading to many unresolved issues. Materials commonly used in hole transport layers suffer from low hole mobility and low glass transition temperatures, preventing electron-hole transport from reaching equilibrium and hindering exciton recombination. Furthermore, the low triplet energy level fails to effectively prevent exciton escape into the hole transport layer, resulting in low luminous efficiency and decreased device stability. On the other hand, total internal reflection at the interface during light emission in OLEDs reduces their light extraction efficiency to approximately 20%, severely limiting performance improvements. Currently, the low refractive index and glass transition temperature of capping materials further limit the improvement in light extraction efficiency, resulting in low overall luminous efficiency for OLEDs.

[0005] To address the aforementioned issues, researching hole transport materials with high hole mobility, high glass transition temperature, and high triplet energy levels, as well as capping materials with high refractive index and glass transition temperature, has become an urgent problem to be solved. Summary of the Invention

[0006] The purpose of this invention is to provide a star-shaped triamine compound and its organic light-emitting device based on existing technology and with industrialization as the goal. This star-shaped triamine compound is applied to the hole transport layer, light-emitting auxiliary layer (second hole transport layer), or capping layer in organic light-emitting devices to develop light-emitting devices with high efficiency and long lifetime. Its general molecular structure is shown in Formula I:

[0007]

[0008] Wherein, at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is selected from the group shown in formula a, and the others are independently selected from the group shown in formula b:

[0009]

[0010] Formula a is fused with one of formulas a-1, a-2, a-3, and a-4, where “^” represents the fusion connection site between formula a and formulas a-1, a-2, a-3, or a-4.

[0011] The R a The same or different from one of the following: hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C6-C25 aromatic ring and C3-C25 aliphatic ring fused ring, or any two adjacent R a Groups bond together to form substituted or unsubstituted cyclic structures;

[0012] The a is selected from 1, 2, or 3; the b is selected from 1, 2, 3, or 4;

[0013] R4 and R5 are independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, and one of the following substituted or unsubstituted groups: silyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, tetrahydronaphthyl, dihydronaphthyl, indenyl, indenyl, or R4 and R5 can be bonded together to form a substituted or unsubstituted cyclic structure; or the carbon atom corresponding to R4 or R5 is a site for bridging L1 to L6;

[0014] R6 is selected from one of the following groups, either substituted or unsubstituted: silyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazoyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, indanyl; or the nitrogen atom corresponding to R6 is a site connected to bridging groups L1 to L6;

[0015] The x that is the same or different is selected from CR c Or N, where x connected to L1, L2, L3, L4, L5, L6 is selected from C atoms;

[0016] R c The same or different from one selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 heterocycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted C2-C25 heteroaryl, or optionally two adjacent Rs. c Groups can bond together to form substituted or unsubstituted cyclic structures;

[0017] R1, R2, and R3 are independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C25 heteroaryl.

[0018] L1, L2, L3, L4, L5, and L6 are independently selected from one of the following: single bond, substituted or unsubstituted C6-C25 arylene, substituted or unsubstituted C2-C25 heteroarylene, substituted or unsubstituted C3-C12 aliphatic ring, and fused and cycloalgides of C6-C25 aromatic rings.

[0019] The condition is that at least one of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, L6, R1, R2, and R3 contains one or more substituted or unsubstituted silyl groups.

[0020] The present invention also provides an organic light-emitting device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains any one or a combination of at least two of the star-shaped triamine compounds described in the present invention.

[0021] The beneficial effects of this invention are:

[0022] This invention provides a star-shaped triamine compound and its organic light-emitting device. The compound is centered on benzene and linked to three triarylamines, with at least one dibenzo5-membered ring attached to each triarylamine. Simultaneously, the structure of Formula I contains at least one substituted or unsubstituted silyl group, which enhances solubility, facilitates film formation, and exhibits good film-forming properties and thermal stability. Furthermore, this type of compound has good hole mobility, appropriate HOMO energy level and T1 value. When applied to organic light-emitting devices, especially as hole transport layer materials and capping layer materials, it can effectively improve the luminous efficiency of the device and extend its lifespan. Detailed Implementation

[0023] The technical solutions of the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are only some embodiments of the present invention, and not all embodiments. Based on the embodiments of the present invention, all other embodiments obtained by those skilled in the art without creative effort are within the protection scope of the present invention.

[0024] In the compounds of the present invention, any atom not specified as a particular isotope is included as any stable isotope of that atom, and includes atoms at both their natural and non-natural isotopic abundances.

[0025] 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.

[0026] For example, Can represent Can represent Can represent And so on. In this specification, when a substituent or linking site lies within a bond that extends through two or more rings, it indicates that it can be linked to any one of the two or more rings, specifically to any one of the corresponding optional sites within the rings. For example, Can represent Can represent And so on.

[0027] The halogens mentioned in this invention refer to fluorine, chlorine, bromine, and iodine.

[0028] 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, isomers 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.

[0029] 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 3 to 6 carbon atoms. Examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, camphenyl, norbornyl, etc., but are not limited thereto. The cycloalkyl group is preferably cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, or norbornyl.

[0030] The silyl group referred to in this invention refers to a silane group formed by removing one hydrogen atom from a silane molecule. Preferably, it is a methylsilyl group. The "substituted or unsubstituted methylsilyl group" has the structure shown as -Si(R)3, where R is selected from any one of H, deuterium, tritium, substituted or unsubstituted C1-C12 alkyl groups, substituted or unsubstituted C3-C15 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C3-C30 alicyclic and C6-C30 aromatic fused cycloyl groups, and substituted or unsubstituted C2-C30 heteroaryl groups, but is not limited thereto; preferably, R... The substituted silyl groups specifically include, but are not limited to, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, etc., but are preferably trimethylsilyl, triethylsilyl, triphenylsilyl, diphenylmethylsilyl, or phenyldimethylsilyl.

[0031] The aryl group described in this invention refers to the general term for a 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 25 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 refers to an aryl group with only one aromatic ring in the molecule, such as phenyl, but not limited thereto; the polycyclic aryl refers to an aryl group containing two or more independent aromatic rings in the molecule, such as biphenyl, terphenyl, etc., but not limited thereto; the fused-ring aryl refers to an aryl group containing two or more aromatic rings fused together by sharing two adjacent carbon atoms, such as naphthyl, anthracene, phenanthryl, pyrene, perylene, fluorene, benzo[a]fluorene, triphenylene, fluoranyl, spirodifluorene, etc., but not limited thereto. The aryl group is preferably phenyl, biphenyl, terphenyl, naphthyl (preferably 2-naphthyl), anthracene (preferably 2-anthrayl), phenanthryl, pyrene, peryl, fluorene, benzo[a]fluorene, triphenylene, or spirodifluorene.

[0032] The heteroaryl group described in this invention refers to the general term for groups 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, or phosphorus atoms, preferably having 1 to 25 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 on a cyclic nitrogen atom. The heteroaryl group can be a monocyclic heteroaryl, a polycyclic heteroaryl, or a fused-ring heteroaryl. The monocyclic heteroaryl groups include, but are not limited to, pyridinyl, pyrimidinyl, triazinyl, furanyl, thiopheneyl, pyrroleyl, imidazolyl, etc.; the polycyclic heteroaryl groups include, but are not limited to, bipyridinyl, bipyrimidinyl, phenylpyridinyl, etc.; the fused-ring heteroaryl groups include, but are not limited to, quinolinyl, isoquinolinyl, indolyl, benzothiopheneyl, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiopheneyl, benzodibenzothiapheneyl, carbazolyl, benzocarbazolyl, acridinel, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, phenoxthiazyl, etc., but are not limited to. 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.

[0033] The arylene group referred to in this invention refers to the general term for the divalent group remaining after removing two hydrogen atoms from the aromatic carbon atom of an aromatic compound molecule. It can be a monocyclic arylene, a polycyclic arylene, or a fused-ring arylene, preferably having 6 to 25 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 arylene includes, but is not limited to, phenylene; the polycyclic arylene includes, but is not limited to, biphenylene, terphenylene; and the fused-ring arylene includes, but is not limited to, naphthylene, anthracene, phenanthrene, fluorene, pyrene, trimethyleneene, fluorene, and phenylfluorene. The aforementioned arylene groups are preferably phenylene, biphenylene, terphenylene, naphthyl, fluorene, or phenylfluorene.

[0034] The heteroaryl group described in this invention refers to the general term for groups obtained by replacing one or more aromatic carbon atoms in an aryl group with heteroatoms, wherein the heteroatoms include, but are not limited to, oxygen, sulfur, nitrogen, or phosphorus atoms. Preferably, it has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 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 group, a polycyclic heteroaryl group, or a fused-ring heteroaryl group. The monocyclic heteroaryl group includes, but is not limited to, pyridinyl, pyrimidinyl, triazinyl, furanyl, and thiopheneyl; the polycyclic heteroaryl group includes, but is not limited to, bipyridinyl, bipyrimidinyl, and phenylpyridinyl; the fused-ring heteroaryl group includes, but is not limited to, quinolineyl, isoquinolineyl, indolyl, benzothiophene, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, benzodibenzofuranyl, dibenzothiaphene, benzodibenzothiaphene, carbazolyl, benzocarbazolyl, acridineyl, 9,10-dihydroacridinyl, phenoxazinyl, phenthiazinyl, and phenoxthiazolyl, but is not limited to. The aforementioned heteroaryl groups are preferably pyridinyl, pyrimidinyl, thiopheneyl, furanyl, benzothiopheneyl, benzofuranyl, benzoxazolyl, benzoimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiopheneyl, benzodibenzothiopheneyl, benzodibenzofuranyl, carbazolyl, acridineyl, phenoxazinyl, phenoxazinyl, and phenoxthiazolyl.

[0035] The fused aliphatic and aromatic rings and cycloalkanes mentioned in this invention refer to the general term for divalent groups remaining after removing two hydrogen atoms from the fused aliphatic and aromatic rings. Preferably, they have 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms, and most preferably 7 to 12 carbon atoms. Examples may include, but are not limited to, benzo[a]cyclopropyl, benzo[a]cyclobutyl, benzo[a]cyclopentyl, benzo[a]cyclohexyl, benzo[a]cycloheptyl, benzo[a]cyclopentenyl, benzo[a]cyclohexenyl, benzo[a]cycloheptenyl, naphtho[a]cyclopropyl, naphtho[a]cyclobutyl, naphtho[a]cyclopentyl, and naphtho[a]cyclohexyl, etc.

[0036] The fused ring of aromatic and aliphatic rings described in this invention refers to a molecule containing one or more aromatic rings and one or more aliphatic rings fused together by sharing two adjacent carbon atoms. The aromatic ring preferably has 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and most preferably 6 to 12 carbon atoms. The aliphatic ring preferably has 3 to 30 carbon atoms, more preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. Examples include benzocyclopropane, benzocyclobutane, benzocyclopentane, benzocyclohexane, benzocycloheptane, benzocyclobutenyl, benzocyclopentenyl, benzocyclohexenyl, naphthocyclopropane, naphthocyclobutane, naphthocyclopentane, naphthocyclohexane, naphthocyclopentenyl, naphthocyclohexenyl, etc., but are not limited thereto.

[0037] The aliphatic ring described in this invention refers to a cyclic hydrocarbon with aliphatic properties, containing a closed carbon ring in the molecule, preferably with 3 to 60 carbon atoms, more preferably 3 to 30 carbon atoms, even more preferably 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and most preferably 3 to 7 carbon atoms. It can form monocyclic or polycyclic hydrocarbons, and can be completely unsaturated or partially unsaturated. Specific examples include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclobutene, cyclopentene, cyclohexene, cycloheptene, etc., but are not limited to these. Multiple monocyclic hydrocarbons can also be connected in various ways: two rings in the molecule can share a carbon atom to form a spiro ring; two carbon atoms on the 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.

[0038] The term "substituted..." as used in this invention refers to monosubstituted or polysubstituted groups, such as substituted silyl, substituted alkyl, substituted cycloalkyl, substituted aryl, substituted aromatic and aliphatic fused ring groups, substituted arylene, substituted aliphatic and aromatic fused and cycloalkanes, etc., which are independently selected from, but not limited to, deuteryl, trityl, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted C6-C20 aryl, substituted or unsubstituted C2-C15 heteroaryl, substituted or unsubstituted amino, etc., preferably selected from deuteryl, trityl, methyl, ethyl, isopropyl, tert-butyl. The following groups are monosubstituted or polysubstituted: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphenyl, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, benzo[a]phenanthrene, perylene, pyrene, benzyl, tolyl, fluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, 9-methyl-9-phenylfluorenyl, diphenylamino, dimethylamino, carbazole, 9-phenylcarbazole, acridine, furanyl, thiophene, benzofuranyl, benzothiophene, benzoxazolyl, benzimidazolyl, benzothiazolyl, dibenzofuranyl, dibenzothiophene, phenothiazinyl, phenothiazinyl, and indole. Furthermore, the above substituents may also be substituted by one or more of the substituents described above, such as deuterium, halogen, cyano, alkyl, cycloalkyl, or aryl.

[0039] Unless otherwise stated, the term "ring" as used herein refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a heterocyclic ring having 2 to 60 carbon atoms, or a combination thereof, which may contain saturated or unsaturated rings.

[0040] In this invention, "at least one" means one, two, three, four, five, six or more.

[0041] In this invention, "one or more" refers to one, two, three, four, five, six or more.

[0042] The cyclic structure formed by bonding as described in this invention refers to two groups being linked together by chemical bonds and optionally aromatized. Examples are shown below:

[0043]

[0044] In this specification, the rings formed by the linkage can be aromatic or non-aromatic rings, and can be three-membered, four-membered, five-membered, six-membered, seven-membered, eight-membered, fused rings, etc., such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, adamantane, norbornene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, isoquinoline, quinazoline, quinoxaline, fluorene, dibenzofuran, dibenzothiophene, carbazole, etc., but not limited to these.

[0045] This invention provides a star-shaped triamine compound, the general molecular structure of which is shown in Formula I:

[0046]

[0047] Wherein, at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is selected from the group shown in formula a, and the others are independently selected from the group shown in formula b:

[0048]

[0049] Formula a is fused with one of formulas a-1, a-2, a-3, and a-4, where “^” represents the fusion connection site between formula a and formulas a-1, a-2, a-3, or a-4.

[0050] The R a The same or different from one of the following: hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C25 aryl, substituted or unsubstituted C2-C25 heteroaryl, substituted or unsubstituted C6-C25 aromatic ring and C3-C25 aliphatic ring fused ring, or any two adjacent R a Groups bond together to form substituted or unsubstituted cyclic structures;

[0051] The a is selected from 1, 2, or 3; the b is selected from 1, 2, 3, or 4;

[0052] R4 and R5 are independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, and one of the following substituted or unsubstituted groups: silyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, tetrahydronaphthyl, dihydronaphthyl, indenyl, indenyl, or R4 and R5 can be bonded together to form a substituted or unsubstituted cyclic structure; or the carbon atom corresponding to R4 or R5 is a site for bridging L1 to L6;

[0053] R6 is selected from one of the following groups, either substituted or unsubstituted: silyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazoyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, indanyl; or the nitrogen atom corresponding to R6 is a site connected to bridging groups L1 to L6;

[0054] The x that is the same or different is selected from CR c Or N, where x connected to L1, L2, L3, L4, L5, L6 is selected from C atoms;

[0055] R c The same or different from one selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C25 heterocycloalkyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted C2-C25 heteroaryl, or optionally two adjacent Rs. c Groups can bond together to form substituted or unsubstituted cyclic structures;

[0056] R1, R2, and R3 are independently selected from any one of hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted C1-C25 silyl, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C25 aryl, and substituted or unsubstituted C2-C25 heteroaryl.

[0057] L1, L2, L3, L4, L5, and L6 are independently selected from one of the following: single bond, substituted or unsubstituted C6-C25 arylene, substituted or unsubstituted C2-C25 heteroarylene, substituted or unsubstituted C3-C12 aliphatic ring, and fused and cycloalgides of C6-C25 aromatic rings.

[0058] The condition is that at least one of Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, L1, L2, L3, L4, L5, L6, R1, R2, and R3 contains one or more silane groups.

[0059] Preferably, formula I is selected from one of the following formulas I-1 to I-3:

[0060]

[0061] Preferably, one, two, three, four, five, or six of the Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are selected from the groups shown in formula a, and the remainder are independently selected from the groups shown in formula b.

[0062] Preferably, at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is selected from the group shown in Formula a, including: one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is selected from the group shown in Formula a, specifically, Ar1, Ar2, Ar3, Ar4, Ar5, or Ar6 is selected from the group shown in Formula a; two of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are selected from the group shown in Formula a, specifically, Ar1 and Ar2, Ar1 and Ar3, Ar1 and Ar5, Ar3 and Ar4, Ar3 and Ar5, or Ar5 and Ar6 are selected from the group shown in Formula a; three of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are selected from the group shown in Formula a, specifically, Ar1, Ar2 and Ar3, Ar1, Ar2 and Ar5, Ar1, Ar3 and Ar4, Ar1, Ar3 and Ar5, Ar1, Ar5 and Ar6, Ar3, Ar2, Ar3, Ar4, Ar5, and Ar6, specifically, Ar1, Ar2, Ar3, Ar3, Ar4, Ar5, and Ar6, Ar1, Ar2, Ar3, Ar4, Ar5, Ar6, Ar5, Ar6, Ar1, Ar2, Ar3, Ar4 ... r4 and Ar5, or Ar3, Ar5 and Ar6 are selected from the groups shown in formula a; four of Ar1, Ar2, Ar3, Ar4, Ar5 and Ar6 are selected from the groups shown in formula a, specifically, Ar1, Ar2, Ar3 and Ar4, Ar1, Ar2, Ar3 and Ar5, Ar1, Ar2, Ar5 and Ar6, Ar1, Ar3, Ar4 and Ar5, or Ar3, Ar4, Ar5 and Ar6 are selected from the groups shown in formula a; five of Ar1, Ar2, Ar3, Ar4, Ar5 and Ar6 are selected from the groups shown in formula a, specifically, Ar1, Ar2, Ar3, Ar4 and Ar5, or Ar1, Ar3, Ar4, Ar5 and Ar6 are selected from the groups shown in formula a; six of Ar1, Ar2, Ar3, Ar4, Ar5 and Ar6 are selected from the groups shown in formula a, specifically, Ar1, Ar2, Ar3, Ar4, Ar5 and Ar6 are selected from the groups shown in formula a.

[0063] Preferably, at least one of the groups represented by formula a contains one or more substituted or unsubstituted silyl groups.

[0064] More preferably, one, two, or three of the groups represented by formula a contain one or more substituted or unsubstituted silyl groups.

[0065] Preferably, at least one of the groups represented by formula b contains one or more substituted or unsubstituted silyl groups.

[0066] More preferably, one, two, or three of the groups shown in formula b contain one or more substituted or unsubstituted silyl groups.

[0067] Preferably, the R c One or more of them are substituted or unsubstituted silyl groups.

[0068] More preferably, the R c One, two, or three of them are substituted or unsubstituted silyl groups.

[0069] Preferably, formula a is selected from one of the following groups:

[0070]

[0071]

[0072] The R a The group is selected, either identically or differently, from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, or one of the following groups, substituted or unsubstituted: trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyl dimethylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, tolyl, biphenyl, terphenyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, indenyl, pyridyl, pyrimidinyl. One of pyrazinyl and pyrazinyl, wherein the "substituted or unsubstituted" substituent is selected from one or more of hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyl dimethylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, camphenyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, or any two adjacent R groups. a Groups bond together to form substituted or unsubstituted benzene rings or naphthalene rings;

[0073] The R mSelected, either identically or differently, from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, trideuterated phenylsilyl, dideuterated phenylmethylsilyl, deuterated phenyldimethylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, tolyl, biphenyl, terphenyl, or any two adjacent R groups. m The groups bond together to form substituted or unsubstituted benzene rings or naphthalene rings; the R m It can also be R mm Replaced by, R mm It is selected from one or more of hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, silyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, camphenyl, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, tolyl, biphenyl, deuterated biphenyl, terphenyl, and deuterated terphenyl, wherein when substituted with multiple substituents, the multiple substituents are the same or different from each other;

[0074] m2 is selected from 1, 2, 3 or 4; m3 is selected from 1, 2, 3, 4, 5 or 6; m4 is selected from 1, 2, 3, 4, 5, 6, 7 or 8; m5 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10; m6 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 or 12; m7 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14.

[0075] More preferably, formula a is selected from one of the following groups:

[0076]

[0077]

[0078] The R bThe substituent is selected, either identically or differently, from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, or substituted or unsubstituted of the following groups: trimethylsilyl, triethylsilyl, triphenylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, wherein the "substituted or unsubstituted" substituent is selected from one or more of hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornyl, phenyl, naphthyl, and in the case of substitution by multiple substituents, the multiple substituents are identical or different from each other, or any two adjacent R groups are identical or different. b Groups bond together to form substituted or unsubstituted benzene rings;

[0079] The a is selected from 1, 2, or 3; the b is selected from 1, 2, 3, or 4; the c is selected from 1, 2, 3, 4, or 5; the d is selected from 1, 2, 3, 4, 5, or 6; the e is selected from 1, 2, 3, 4, 5, 6, or 7; the f is selected from 1, 2, 3, 4, 5, 6, 7, or 8; the g is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the h is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; and the i is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11.

[0080] Preferably, the R a Selected, either identically or differently, from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, and one of the following groups, substituted or unsubstituted: trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyl dimethylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, tolyl, biphenyl, terphenyl, tetrahydronaphthyl, dihydronaphthyl One of indene, indene, or indene, wherein the "substituted or unsubstituted" substituent is selected from one or more of hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, trimethylsilyl, triethylsilyl, triphenylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, deuterated phenyl, naphthyl, and deuterated naphthyl. In the case of substitution by multiple substituents, the multiple substituents may be the same as or different from each other, or any two adjacent R groups may be different. a Groups bond together to form substituted or unsubstituted benzene rings.

[0081] Preferably, R of formula I aOne or more of them are selected from substituted or unsubstituted silyl groups.

[0082] More preferably, R of Formula I a One, two, or three of them are selected from substituted or unsubstituted silyl groups.

[0083] Preferably, R6 is selected from one of the following groups, substituted or unsubstituted: trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyl dimethylsilyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazoyl, tetrahydronaphthyl, dihydronaphthyl, indenyl, and indenyl. The substituents in the "substituted or unsubstituted" group are selected from one or more of hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, camphenyl, phenyl, deuterated phenyl, naphthyl, and deuterated naphthyl. In the case of substitution by multiple substituents, the multiple substituents are the same or different from each other; or the nitrogen atom corresponding to R6 is a site connected to bridging L1 to L6.

[0084] Preferably, formula b is selected from one of the following groups:

[0085]

[0086]

[0087] The R e The same or different elements are selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, trimethylsilyl, triphenylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, camphenyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, deuterated phenyl, deuterated naphthyl, and deuterated biphenyl; wherein R e It can also be R ee Replaced by, R eeIt is selected from one or more of hydrogen, deuterium, tritium, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, tolyl, biphenyl, deuterated biphenyl, terphenyl, and deuterated terphenyl;

[0088] The c1 is selected from 1, 2, 3, 4, or 5; the c2 is selected from 1, 2, 3, or 4; the c3 is selected from 1, 2, or 3; the c4 is selected from 1, 2, 3, 4, 5, 6, or 7; the c5 is selected from 1 or 2; the c6 is selected from 1, 2, 3, 4, 5, or 6; the c7 is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the c8 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; the c9 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10; the c 10 Choose from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11.

[0089] Preferably, the R c The same or different Rs are selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, phenyldimethylsilyl, trideuterated phenylsilyl, dideuterated phenylmethylsilyl, deuterated phenyldimethylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, camphenyl, phenyl, naphthyl, tolyl, biphenyl, terphenyl, anthracene, phenanthrene, phenylenetriene, spirofluorenyl, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, deuterated phenyl, deuterated naphthyl, deuterated biphenyl, or any two adjacent Rs. c The groups can bond together to form a benzene ring; wherein the R c It can also be R cc Replaced by, R cc It is selected from one or more of hydrogen, deuterium, tritium, trimethylsilyl, triphenylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, deuterated phenyl, naphthyl, deuterated naphthyl, tolyl, biphenyl, deuterated biphenyl, terphenyl, deuterated terphenyl, anthracene, and phenanthrene, wherein when substituted with multiple substituents, the multiple substituents are the same or different from each other.

[0090] Preferably, R of formula I c One or more of them are selected from substituted or unsubstituted silyl groups.

[0091] More preferably, R of Formula I cOne, two, or three of them are selected from substituted or unsubstituted silyl groups.

[0092] Preferably, L1, L2, L3, L4, L5, and L6 are independently selected from single-bonded, substituted, or unsubstituted groups of the following: phenyl, naphthyl, anthracene, phenanthrene, triphenylene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, phenyl-naphthyl, naphthyl-naphthyl, dibenzofuranyl, dibenzothiopheneyl, carbazolyl, tetrahydronaphthyl, dihydronaphthyl, indene, indene, and combinations thereof, wherein the substituent is one or more of deuterium, tritium, cyano, halogen, trifluoromethyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, deuterated phenyl, deuterated naphthyl, tolyl, biphenyl, terphenyl, and naphthyl. In the case of being substituted by multiple substituents, the multiple substituents may be the same as or different from each other.

[0093] Preferably, L1, L2, L3, L4, L5, and L6 are independently selected from single bonds or one of the following groups:

[0094]

[0095] The R d They may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, substituted or unsubstituted C1-C25 silyl, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C12 cycloalkyl, and substituted or unsubstituted C6-C25 aryl.

[0096] The d0 is selected from 0, 1, or 2; the d1 is selected from 0, 1, 2, 3, or 4; the d2 is selected from 0, 1, 2, 3, 4, 5, or 6; the d3 is selected from 0, 1, 2, 3, 4, 5, 6, 7, or 8.

[0097] The R x R y The group is independently selected from hydrogen, deuterium, tritium, cyano, halogen, trifluoromethyl, or substituted or unsubstituted of the following groups: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, anthracene, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazoyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, and indole;

[0098] The R zSelected from the following groups, whether substituted or unsubstituted: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, norbornel, phenyl, naphthyl, anthracene, phenanthrene, triphenylene, dibenzofuranyl, dibenzothiophene, 9,9-dimethylfluorenyl, 9,9-diphenylfluorenyl, spirofluorenyl, 9-phenylcarbazoyl, tetrahydronaphthyl, dihydronaphthyl, indanyl, and indanyl.

[0099] Most preferably, L1, L2, L3, L4, L5, and L6 are independently selected from single bonds or one of the following groups:

[0100]

[0101] Preferably, Formula I contains one or more of the substituted or unsubstituted silyl groups.

[0102] More preferably, Formula I contains one, two, three, four, five, six or more of the substituted or unsubstituted silyl groups.

[0103] Preferably, the substituted or unsubstituted silyl group is selected from trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylmethylsilyl, and phenyldimethylsilyl.

[0104] Most preferably, the star-shaped triamine compound is selected from any one of the following chemical structures:

[0105]

[0106]

[0107]

[0108]

[0109]

[0110]

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126]

[0127]

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134]

[0135] The method for preparing the star-shaped triamine compound of Formula I of the present invention can be achieved through conventional coupling reactions in the art, for example, through the following synthetic route, but the present invention is not limited thereto:

[0136]

[0137] In this invention, a star-shaped triamine compound is coupled with an intermediate A, B, and C via a Buchwald-Hartwig coupling reaction. The starting material g and intermediate A are coupled with an intermediate A via a Buchwald-Hartwig coupling reaction to obtain intermediate I. Intermediate I and intermediate B are coupled with an intermediate B via a Buchwald-Hartwig coupling reaction to obtain intermediate II. Intermediate II and intermediate C are coupled with an intermediate C via a Buchwald-Hartwig coupling reaction to finally obtain the compound of formula I, wherein the halogen compounds X1, X2, X3, X4, X5, and X6 are independently selected from Cl, Br, or I.

[0138] This invention does not impose any particular restrictions on the source of the raw materials used in the above-described reactions. Commercially available raw materials or preparation methods well-known to those skilled in the art can be used to obtain the star-shaped triamine compound represented by Formula I as described in this invention. This invention also does not impose any particular restrictions on the above reactions; conventional reactions well-known to those skilled in the art can be used.

[0139] The present invention also provides an organic light-emitting device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer contains any one or a combination of at least two of the star-shaped triamine compounds described in the present invention.

[0140] Preferably, the organic layer comprises a hole transport region, a light-emitting layer, an electron transport region, or a capping layer, and at least one of the hole transport region and the capping layer contains any one or a combination of at least two of the star-shaped triamine compounds described in this invention.

[0141] Preferably, the organic layer includes a hole transport region containing any one or a combination of at least two of the star-shaped triamine compounds described in this invention.

[0142] Preferably, the hole transport region comprises at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, wherein the hole transport layer contains any one or a combination of at least two of the star-shaped triamine compounds described in this invention.

[0143] Preferably, the hole transport layer comprises a hole transport layer and a light-emitting auxiliary layer (second hole transport layer), the light-emitting auxiliary layer being located between the hole transport layer and the light-emitting layer, and at least one of the hole transport layer and the light-emitting auxiliary layer contains any one or a combination of at least two of the star-shaped triamine compounds described in this invention.

[0144] Preferably, the organic layer includes a capping layer containing any one or a combination of at least two of the star-shaped triamine compounds described in this invention.

[0145] Preferably, the capping layer of the present invention may be a single-layer structure, a two-layer structure, or a multi-layer structure, and the capping layer material of the present invention is at least selected from the star-shaped triamine compound of the present invention, or contains conventional capping layer materials well known to those skilled in the art.

[0146] The light-emitting device of the present invention is typically formed on a substrate. The substrate can be any material that remains unchanged during the formation of electrodes and organic layers; for example, substrates made of glass, plastic, polymer films, silicon, etc. When the substrate is opaque, the electrodes opposite it are preferably transparent or translucent.

[0147] For anode materials, metals, alloys, conductive compounds, and mixtures thereof with high work functions (e.g., above 4.0 eV) are preferred. Examples include indium tin oxide (ITO); indium tin oxide containing silicon or silicon oxide; indium zinc oxide; indium oxide containing tungsten oxide and zinc oxide; and graphene. Other materials include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (e.g., titanium nitride).

[0148] The anode can have a single-layer structure or a multi-layer structure comprising two or more layers. For example, the anode can have a three-layer structure of ITO / Ag / ITO, but the structure of the anode is not limited to this. Preferably, the anode of the present invention uses a transparent ITO substrate. The anode can be formed by depositing or spraying the material used to form the anode onto the substrate.

[0149] The hole transport region may include multiple single-layer structures of different materials, such as a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / buffer layer structure, a hole injection layer / buffer layer structure, a hole transport layer / buffer layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein the layers of each structure are stacked sequentially from the anode in the order described, but the structure of the hole transport region is not limited to this.

[0150] For the hole injection layer material, materials with high hole injection properties are preferred, such as rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide. Alternatively, low-molecular-weight organic compounds such as 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (MTDATA), and 4,4'-bis[N-(4-diphenylamino)]triphenylamine (MTDATA) can also be selected. Aromatic amine compounds such as 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviated as DNTPD), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA1), and 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviated as PCzPCA2) are used. These compounds can be single-component structures or single-layer or multi-layer structures formed from different substances. Besides the above materials and their combinations, other known materials suitable for hole injection layers can also be selected.

[0151] For the hole transport layer material, materials with high hole transport properties are preferred. Aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc., can be used. Examples of aromatic amine compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (BAFLP), and 4,4'-bis[N-(9,9-dimethylfluorene-9-yl]triphenylamine (BAFLP). [2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4”-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). Examples of carbazole derivatives include 4,4'-bis(9-carbazolyl)biphenyl (CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole (PCzPA); and anthracene derivatives include 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (t-BuDNA), 9,10-bis(2-naphthyl)anthracene (DNA), and 9,10-diphenylanthracene (DPAnth). Polymers such as poly(N-vinylcarbazole) (PVK) can also be used. Preferably, the hole transport layer material is selected from any one or a combination of at least two of the star-shaped triamine compounds described in this invention.

[0152] The emissive layer is a layer with light-emitting function. It includes a host material and dopant materials and emits light via fluorescence or phosphorescence. The emissive layer can be formed with a thickness ranging from 10 nm to 60 nm. The emissive layer can be formed to emit light of a specific color. For example, the emissive layer can be formed as a red emissive layer, a green emissive layer, or a blue emissive layer.

[0153] Blue fluorescent materials used as the luminescent layer can be pyrene derivatives, styrylamine derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Examples include N4-(9H-carbazole-9-yl)-4'-(10-phenyl-9-anthrayl)triphenylamine (YGAPA) and 4-(10-phenyl-9-anthrayl)-4'-(9-phenyl-9H-carbazole-3-yl)triphenylamine (PCBAPA). Blue phosphorescent materials used as the luminescent layer can be metal complexes such as iridium complexes, osmium complexes, and platinum complexes. Examples include bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)tetra(1-pyrazolyl)borate (FIr6), bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (FIrpic), bis[2-(3',5'-bis(trifluoromethyl)phenyl)pyridine-N,C2']iridium(III)pyridinecarboxylate (Ir(CF3ppy)2(pic)), and bis[2-(4',6'-difluorophenyl)pyridine-N,C2']iridium(III)acetylacetone (FIracac). Besides these materials, other known materials suitable for blue luminescence can also be selected.

[0154] Green fluorescent materials used as the luminescent layer can utilize aromatic amine derivatives, such as N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviated as 2PCABPhA), N-(9,10-diphenyl-2-anthrayl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthrayl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviated as 2DPABPhA), and N,N,9-triphenylanthracene-9-amine (abbreviated as DPhAPhA). For green phosphorescent materials used as the luminescent layer, iridium complexes can be used. Examples include tris(2-phenylpyridine-N,C2')iridium(III) (abbreviated as Ir(ppy)3), bis(2-phenylpyridine-N,C2')iridium(III)acetylacetonate (abbreviated as Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazole)iridium(III)acetylacetonate (abbreviated as Ir(pbi)2(acac)), and bis(benzo[h]quinoline)iridium(III)acetylacetonate (abbreviated as Ir(bzq)2(acac)). Besides these materials, other known green phosphorescent materials can also be selected.

[0155] Red-based fluorescent materials used as the luminescent layer can be tetraphenyl derivatives, diamine derivatives, etc., such as N,N,N',N'-tetra(4-methylphenyl)tetraphenyl-5,11-diamine (p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetra(4-methylphenyl)acenaphthene[1,2-a]fluoranthene-3,10-diamine (p-mPhAFD). Red-based phosphorescent materials used as the luminescent layer can be metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes. Examples of organometallic complexes include bis[2-(2'-benzo[4,5-α]thienyl)pyridine-N,C3']iridium(III)acetylacetonate (abbreviated as Ir(btp)2(acac)), bis(1-phenylisoquinoline-N,C2')iridium(III)acetylacetonate (abbreviated as Ir(piq)2(acac)), (acetylacetonate)bis[2,3-bis(4-fluorophenyl)quinoxaline]iridium(III) (abbreviated as Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviated as PtOEP). Besides these materials, other known materials suitable for red luminescence can also be selected.

[0156] The light-emitting layer can be formed by dispersing the aforementioned doped material in other materials (the host material).Main materials, such as (1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes, such as tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq), tris(4-methyl-8-hydroxyquinoline)aluminum(III) (abbreviated as Almq3), bis(10-hydroxybenzo[h]quinoline)beryllium(II) (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq); (2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, phenanthroline derivatives, etc., such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as PBD), 2,2',2”-(1,3,5-phenyltriyl)tris(1-phenyl-1H-benzimidazole) (abbreviated as TPBI), phenanthrene-rhein (abbreviated as BPhen), copper oxychloride (abbreviated as BCP) and other heterocyclic compounds; (3) fused aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, etc., such as 9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviated as CzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviated as DPPA), 9,10-bis(2-naphthyl)anthracene (abbreviated as DNA), 2-tert-butyl-9,10-bis(2-naphthyl)anthracene (abbreviated as t-BuDNA), 9,9'-bi Anthracene (abbreviated as BANT), 9,9'-(brus-3,3'-diyl)diphenanthrene (abbreviated as DPNS), 3,3',3”-(benzene-1,3,5-triyl)tripyrene (abbreviated as TPB3), 9,10-diphenylanthracene (abbreviated as DPANth) and other fused aromatic compounds; (4) Aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives, such as N,N-diphenyl-9-[4-(10-phenyl-9-anthrayl)phenyl]-9H-carbazole-3-amine (abbreviated as CzA1PA), 4-(10-phenyl-9-anthrayl)triphenylamine (abbreviated as DPhPA), N,9-diphenyl-N ... Aromatic amine compounds such as 3-oxazolium-3-amine (PCAPA), N-(9,10-diphenyl-2-anthrayl)-N,9-diphenyl-9H-carbazole-3-amine (2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bisfluorene-2-yl)-N-phenylamino]biphenyl (BSPB).In addition to the materials mentioned above, other known materials suitable for use as the main body can also be selected.

[0157] The optimal doping ratio of the host material and guest material of the light-emitting layer can vary depending on the material used. Typically, the doping mass percentage of the guest material of the light-emitting layer is 0.01% to 20%, preferably 0.1% to 15%, and more preferably 1% to 10%.

[0158] The electron transport layer material is selected from materials with high electron transport properties. The electron transport layer may include a first electron transport layer material and a second electron transport layer material. The electron transport layer material may be selected from metal complexes such as (1) aluminum complexes, beryllium complexes, zinc complexes, etc., such as tris(8-hydroxyquinoline)aluminum(III) (abbreviated as Alq), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviated as BeBq2), bis(2-methyl-8-hydroxyquinoline)(4-phenylphenol)aluminum(III) (abbreviated as BAlq), bis(8-hydroxyquinoline)zinc(II) (abbreviated as Znq), and bis[2-(2-benzoxazolyl)phenol]zinc(II) (abbreviated as ZnPBO). (2) Imidazole derivatives, benzimidazole derivatives, azazine derivatives, carbazole derivatives, phenanthrene derivatives and other heteroaromatic compounds, such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviated as: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviated as: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviated as: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviated as: p-EtTAZ), phenanthrene (abbreviated as: BPhen), and copper bath (abbreviated as: BCP). (3) Polymer compounds, such as poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py), in addition to the above materials, other known materials suitable for electron transport layers can also be selected.

[0159] The electron injection layer material is selected based on its high electron injection performance. Alkali metals, alkaline earth metals, or their compounds, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx), can be used for the electron injection layer. In addition to the above materials, other known suitable materials can also be selected for the electron injection layer.

[0160] Cathode materials preferably use metals, alloys, conductive compounds, and mixtures thereof with low work functions (specifically below 3.8 eV). Examples include elements belonging to Group 1 or Group 2 of the periodic table, namely alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing them.

[0161] The capping layer material is used to reduce total emission loss and waveguide loss in OLED devices and improve light extraction efficiency. The capping layer material of this invention can be selected from Alq3, TPBi, etc., or other known materials suitable for capping layers, or the star-shaped triamine compound described in this invention.

[0162] The organic light-emitting device described in this invention can be selected and combined according to device parameter requirements and material characteristics, and some organic layers can be added or omitted. For example, an electron buffer layer can be added between the electron transport layer and the electron injection layer; organic layers with the same function can also be made into a stacked structure of two or more layers, for example, the electron transport layer can also have a first electron transport layer and a second electron transport layer.

[0163] There are no particular restrictions on the preparation and formation methods of each layer in the organic light-emitting device. Any one of the following methods can be used: vacuum evaporation, spin coating, vapor deposition, blade coating, laser thermal transfer, electrospray coating, slot coating, and dip coating. In this invention, vacuum evaporation is preferred.

[0164] The organic light-emitting device described in this invention can be widely used in panel displays, lighting sources, flexible OLEDs, electronic paper, organic solar cells, organic photosensitive materials or organic thin-film transistors, signs, signal lights and other fields.

[0165] The invention is explained in more detail through the following examples, but is not intended to limit the invention. Based on this description, those skilled in the art will be able to practice the invention and prepare other compounds and devices according to the invention within the entire scope disclosed without inventive effort.

[0166] Preparation and characterization of compounds

[0167] Description of raw materials, reagents, and characterization equipment:

[0168] 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.

[0169] Mass spectrometry was performed using a Waters G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer, with chloroform as the solvent.

[0170] Elemental analysis was performed using a Vario EL cube organic elemental analyzer from Elementar GmbH, Germany, with sample masses ranging from 5 to 10 mg.

[0171] Synthesis Example 1: Preparation of Compound 3

[0172]

[0173] Step 1: Synthesize intermediate A-3

[0174] Under nitrogen protection, a-3 (13.35 g, 85.00 mmol), b-3 (7.92 g, 85.00 mmol), and sodium tert-butoxide (12.25 g, 127.50 mmol) dissolved in 400 mL of toluene were added to a reaction flask. Pd(dppf)Cl2 (0.75 g, 1.02 mmol) was added with stirring, and the mixture was heated to reflux for 4 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate yielded intermediate A-3 (12.51 g, 87%), with a solid purity ≥99.79% as determined by HPLC. Mass spectrometry m / z: 169.0880 (theoretical value: 169.0891).

[0175] Step 2: Synthesize intermediate C-3

[0176] Under nitrogen protection, e-3 (8.02 g, 35.00 mmol), f-3 (7.33 g, 35.00 mmol), and sodium tert-butoxide (5.05 g, 52.50 mmol) were dissolved in 200 mL of toluene. Pd(OAc)₂ (0.08 g, 0.35 mmol) and P(t-Bu)₃ (1.40 mL, 0.70 mmol, 0.5 M toluene solution) were added with stirring. The mixture of the above reactants was heated under reflux for 5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene / methanol (7:1 v / v) yielded intermediate C-3 (10.64 g, 85%), with a solid purity ≥99.83% as determined by HPLC. Mass spectrometry m / z: 357.1925 (theoretical value: 357.1913).

[0177] Step 3: Synthesize intermediate I-3

[0178] Under nitrogen protection, intermediates A-3 (11.85 g, 70.00 mmol), g-3 (9.46 g, 35.00 mmol), and sodium tert-butoxide (6.73 g, 70.00 mmol) were dissolved in 320 mL of toluene. Pd(OAc)₂ (0.16 g, 0.70 mmol) and P(t-Bu)₃ (2.80 mL, 1.40 mmol, 0.5 M toluene solution) were added with stirring. The mixture was heated under reflux for 4.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography with n-hexane / dichloromethane (8:1 v / v) to obtain intermediate I-3 (12.67 g, 81%), with a solid purity ≥99.89% as determined by HPLC. Mass spectrometry m / z: 446.1559 (theoretical value: 446.1550).

[0179] Step 4: Synthesize compound 3

[0180] Under nitrogen protection, intermediates I-3 (11.17 g, 25.00 mmol), C-3 (8.94 g, 25.00 mmol), and sodium tert-butoxide (3.60 g, 37.50 mmol) were dissolved in 150 mL of toluene. Pd₂(dba)₃ (0.23 g, 0.25 mmol) and X-Phos (0.24 g, 0.50 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene gave compound 3 (14.59 g, 76%), with a solid purity ≥ 99.94% as determined by HPLC. Mass spectrometry m / z: 767.3685 (theoretical value: 767.3696). Theoretical elemental content (%) C 54 H 49 N3Si: C, 84.44; H, 6.43; N, 5.47. Measured elemental content (%): C, 84.47; H, 6.41; N, 5.44.

[0181] Synthesis Example 2: Preparation of Compound 11

[0182]

[0183] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-11, e-3 with an equimolar amount of e-11, and f-3 with an equimolar amount of f-11, while the other steps remained the same, yielding compound 11 (16.62 g). HPLC analysis showed a solid purity ≥ 99.90%. Mass spectrometry m / z: 897.4488 (theoretical value: 897.4478). Theoretical elemental content (%) C 64H 59 N3Si: C, 85.57; H, 6.62; N, 4.68. Measured elemental content (%): C, 85.55; H, 6.65; N, 4.64.

[0184] Synthesis Example 3: Preparation of Compound 19

[0185]

[0186] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-19, and e-3 was replaced with an equimolar amount of e-11. All other steps remained the same, yielding compound 19 (17.30 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 947.2736 (theoretical value: 947.2754). Theoretical elemental content (%) C 54 H 39 F 10 N3Si: C, 68.42; H, 4.15; N, 4.43. Measured elemental content (%): C, 68.39; H, 4.18; N, 4.41.

[0187] Synthesis Example 4: Preparation of Compound 25

[0188]

[0189] In Synthesis Example 1, e-3 was replaced with an equimolar amount of e-11, and f-3 was replaced with an equimolar amount of f-25. All other steps remained the same, yielding compound 25 (14.73 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 817.3870 (theoretical value: 817.3852). Theoretical elemental content (%) C 58 H 51 N3Si: C, 85.15; H, 6.28; N, 5.14. Measured elemental content (%): C, 85.17; H, 6.31; N, 5.11.

[0190] Synthesis Example 5: Preparation of Compound 32

[0191]

[0192] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-32, and e-3 was replaced with an equimolar amount of e-11. All other steps remained the same, yielding compound 32 (17.26 g). HPLC analysis showed a solid purity ≥ 99.97%. Mass spectrometry m / z: 919.4337 (theoretical value: 919.4322). Theoretical elemental content (%) C 66 H 57N3Si: C, 86.14; H, 6.24; N, 4.57. Measured elemental content (%): C, 86.12; H, 6.23; N, 4.59.

[0193] Synthesis Example 6: Preparation of Compound 44

[0194]

[0195] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-44, and e-3 was replaced with an equimolar amount of e-44. All other steps remained the same, yielding compound 44 (19.31 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 1071.5325 (theoretical value: 1071.5343). Theoretical elemental content (%) C 75 H 73 N3Si2: C, 83.99; H, 6.86; N, 3.92. Measured elemental content (%): C, 83.96; H, 6.84; N, 3.95.

[0196] Synthesis Example 7: Preparation of Compound 49

[0197]

[0198] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-32, e-3 with an equimolar amount of e-49, and f-3 with an equimolar amount of b-3, while maintaining the same other steps, yielding compound 49 (17.03 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 919.4336 (theoretical value: 919.4322). Theoretical elemental content (%) C 66 H 57 N3Si: C, 86.14; H, 6.24; N, 4.57. Measured elemental content (%): C, 86.17; H, 6.26; N, 4.53.

[0199] Synthesis Example 8: Preparation of Compound 152

[0200]

[0201] In Synthesis Example 1, a-3 was replaced with an equimolar amount of e-11, b-3 with an equimolar amount of b-152, and e-3 with an equimolar amount of e-152, while the other steps remained the same, yielding compound 152 (19.03 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 1041.4859 (theoretical value: 1041.4874). Theoretical elemental content (%) C 73 H 67N3Si2: C, 84.10; H, 6.48; N, 4.03. Measured elemental content (%): C, 84.13; H, 6.45; N, 4.06.

[0202] Synthesis Example 9: Preparation of Compound 194

[0203]

[0204] In Synthesis Example 1, a-3 was replaced with an equimolar amount of e-11, e-3 with an equimolar amount of e-194, and f-3 with an equimolar amount of b-3, while the other steps remained the same, yielding compound 194 (15.46 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 846.4537 (theoretical value: 846.4530). Theoretical elemental content (%) C 57 H 50 D7N3Si2: C, 80.80; H, 7.61; N, 4.96. Measured elemental content (%): C, 80.82; H, 7.59; N, 4.93.

[0205] Synthetic Example 10: Preparation of Compound 198

[0206]

[0207] In Synthesis Example 1, a-3 was replaced with an equimolar amount of e-11, e-3 with an equimolar amount of e-198, and f-3 with an equimolar amount of b-3, while the other steps remained the same, yielding compound 198 (16.49 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 915.4414 (theoretical value: 915.4404). Theoretical elemental content (%) C 63 H 61 N3Si2: C, 82.57; H, 6.71; N, 4.59. Measured elemental content (%): C, 82.55; H, 6.68; N, 4.61.

[0208] Synthesis Example 11: Preparation of Compound 202

[0209]

[0210] In Synthesis Example 1, e-3 was replaced with an equimolar amount of e-11, and f-3 was replaced with an equimolar amount of f-202. All other steps remained the same, yielding compound 202 (16.02 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 901.4774 (theoretical value: 901.4791). Theoretical elemental content (%) C 64 H 63N3Si: C, 85.19; H, 7.04; N, 4.66. Measured elemental content (%): C, 85.17; H, 7.06; N, 4.61.

[0211] Synthesis Example 12: Preparation of Compound 208

[0212]

[0213] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-208, e-3 with an equimolar amount of e-208, and f-3 with an equimolar amount of b-3, while the other steps remained the same, yielding compound 208 (19.54 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 1115.5958 (theoretical value: 1115.5969). Theoretical elemental content (%) C 78 H 81 N3Si2: C, 83.90; H, 7.31; N, 3.76. Measured elemental content (%): C, 83.93; H, 7.28; N, 3.79.

[0214] Synthesis Example 13: Preparation of Compound 211

[0215]

[0216] In Synthesis Example 1, e-3 was replaced with an equimolar amount of e-11, and f-3 was replaced with an equimolar amount of f-211. All other steps remained the same, yielding compound 211 (16.36 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 843.4020 (theoretical value: 843.4009). Theoretical elemental content (%) C 60 H 53 N3Si: C, 85.37; H, 6.33; N, 4.98. Measured elemental content (%): C, 85.40; H, 6.31; N, 4.96.

[0217] Synthesis Example 14: Preparation of Compound 261

[0218]

[0219] In Synthesis Example 1, e-3 was replaced with an equimolar amount of e-261, and f-3 was replaced with an equimolar amount of b-3, with all other steps remaining the same, yielding compound 261 (16.73 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 891.4022 (theoretical value: 891.4009). Theoretical elemental content (%) C 64 H 53N3Si: C, 86.15; H, 5.99; N, 4.71. Measured elemental content (%): C, 86.17; H, 5.97; N, 4.68.

[0220] Synthesis Example 15: Preparation of Compound 267

[0221]

[0222] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-267, b-3 with an equimolar amount of b-267, e-3 with an equimolar amount of e-11, and f-3 with an equimolar amount of f-267, while the other steps remained the same, yielding compound 267 (17.68 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 981.5275 (theoretical value: 981.5262). Theoretical elemental content (%) C 70 H 51 D 10 N3Si: C, 85.58; H, 7.28; N, 4.28. Measured elemental content (%): C, 85.61; H, 7.25; N, 4.25.

[0223] Synthesis Example 16: Preparation of Compound 289

[0224]

[0225] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-289, e-3 with an equimolar amount of e-11, and f-3 with an equimolar amount of f-267. All other steps remained the same, yielding compound 289 (18.86 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 1061.5749 (theoretical value: 1061.5765). Theoretical elemental content (%) C 76 H 43 D 18 N3Si: C, 85.91; H, 7.49; N, 3.95. Measured elemental content (%): C, 85.88; H, 7.52; N, 3.93.

[0226] Synthesis Example 17: Preparation of Compound 293

[0227]

[0228] Step 1: Synthesize intermediate A-293

[0229] Under nitrogen protection, a-293 (9.72 g, 60.00 mmol), b-3 (5.59 g, 60.00 mmol), and sodium tert-butoxide (8.65 g, 90.00 mmol) were dissolved in 300 mL of toluene. Pd(dppf)Cl2 (0.53 g, 0.72 mmol) was added with stirring, and the mixture was heated under reflux for 4 h. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate yielded intermediate A-293 (9.20 g, 88%), with a solid purity ≥99.36% as determined by HPLC. Mass spectrometry m / z: 174.1218 (theoretical value: 174.1205).

[0230] Step 2: Synthesize intermediate B-293

[0231] Under nitrogen protection, c-293 (12.86 g, 50.00 mmol), b-3 (4.66 g, 50.00 mmol), and sodium tert-butoxide (7.21 g, 75.00 mmol) were dissolved in 250 mL of toluene. Pd(dppf)Cl2 (0.44 g, 0.60 mmol) was added with stirring, and the mixture was heated under reflux for 4.5 h. After the reaction was complete, the reaction solution was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from ethyl acetate yielded intermediate B-293 (11.58 g, 86%), with a solid purity ≥99.53% as determined by HPLC. Mass spectrometry m / z: 269.1211 (theoretical value: 269.1204).

[0232] Step 3: Synthesize intermediate C-267

[0233] Under nitrogen protection, e-11 (9.17 g, 40.00 mmol), f-267 (13.34 g, 40.00 mmol), and sodium tert-butoxide (7.68 g, 80.00 mmol) were dissolved in 200 mL of toluene. Pd(OAc)₂ (0.09 g, 0.40 mmol) and P(t-Bu)₃ (1.60 mL, 0.80 mmol, 0.5 M toluene solution) were added with stirring. The mixture of the above reactants was heated under reflux for 4.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene / methanol (10:1 v / v) yielded intermediate C-267 (15.80 g, 82%), with a solid purity ≥99.79% as determined by HPLC. Mass spectrometry m / z: 481.2211 (theoretical value: 481.2226).

[0234] Step 4: Synthesize intermediate I-293

[0235] Under nitrogen protection, intermediates A-293 (7.84 g, 45.00 mmol), g-293 (14.28 g, 45.00 mmol), and sodium tert-butoxide (6.49 g, 67.50 mmol) were dissolved in 250 mL of toluene. Pd(OAc)₂ (0.10 g, 0.45 mmol) and P(t-Bu)₃ (1.80 mL, 0.90 mmol, 0.5 M toluene solution) were added with stirring. The mixture was heated under reflux for 5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography with n-hexane / dichloromethane (9:1 v / v) to obtain intermediate I-293 (12.93 g, 79%), with a solid purity ≥99.83% as determined by HPLC. Mass spectrometry m / z: 362.0248 (theoretical value: 362.0234).

[0236] Step 5: Synthesize intermediate II-293

[0237] Under nitrogen protection, intermediates I-293 (12.73 g, 35.00 mmol), B-293 (9.43 g, 35.00 mmol), and sodium tert-butoxide (5.05 g, 52.50 mmol) were dissolved in 200 mL of toluene. Pd₂(dba)₃ (0.32 g, 0.35 mmol) and P(t-Bu)₃ (1.40 mL, 0.70 mmol, 0.5 M toluene solution) were added with stirring. The mixture of the above reactants was heated under reflux for 5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was purified by silica gel column chromatography with n-hexane / dichloromethane (6:1 v / v) to obtain intermediate II-293 (14.88 g, 77%), with a solid purity ≥99.85% as determined by HPLC. Mass spectrometry m / z: 551.2159 (theoretical value: 551.2177).

[0238] Step 6: Synthesize compound 293

[0239] Under nitrogen protection, intermediates II-293 (13.80 g, 25.00 mmol), C-267 (12.04 g, 25.00 mmol), and sodium tert-butoxide (3.84 g, 40.00 mmol) were dissolved in 150 mL of toluene. Pd₂(dba)₃ (0.23 g, 0.25 mmol) and X-Phos (0.24 g, 0.50 mmol) were added with stirring. The mixture of the above reactants was heated under reflux for 6 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. Recrystallization from toluene yielded compound 293 (18.45 g, 74%), with a solid purity ≥ 99.94% as determined by HPLC. Mass spectrometry m / z: 996.4648 (theoretical value: 996.4636). Theoretical elemental content (%) C 72 H 52 D5N3Si: C, 86.71; H, 6.27; N, 4.21. Measured elemental content (%): C, 86.74; H, 6.25; N, 4.19.

[0240] Synthetic Example 18: Preparation of Compound 313

[0241]

[0242] In Synthesis Example 1, a-3 was replaced with an equimolar amount of e-11, b-3 with an equimolar amount of b-313, e-3 with an equimolar amount of e-313, and f-3 with an equimolar amount of b-3, while the other steps remained the same, yielding compound 313 (19.57 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 1071.5325 (theoretical value: 1071.5343). Theoretical elemental content (%) C 75 H 73 N3Si2: C, 83.99; H, 6.86; N, 3.92. Measured elemental content (%): C, 83.95; H, 6.88; N, 3.89.

[0243] Synthesis Example 19: Preparation of Compound 331

[0244]

[0245]

[0246] In Synthesis Example 1, a-3 was replaced with an equimolar amount of e-11, e-3 with an equimolar amount of e-331, and f-3 with an equimolar amount of b-3, while the other steps remained the same, yielding compound 331 (18.80 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 1043.5021 (theoretical value: 1043.5030). Theoretical elemental content (%) C 73 H 69 N3Si2: C, 83.94; H, 6.66; N, 4.02. Measured elemental content (%): C, 83.97; H, 6.64; N, 4.04.

[0247] Synthesis Example 20: Preparation of Compound 333

[0248]

[0249] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-333, e-3 with an equimolar amount of e-11, and f-3 with an equimolar amount of f-333, while the other steps remained the same, yielding compound 333 (18.28 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 1000.4933 (theoretical value: 1000.4949). Theoretical elemental content (%) C 72 H 56 D5N3Si: C, 86.36; H, 6.64; N, 4.20. Measured elemental content (%): C, 86.39; H, 6.66; N, 4.16.

[0250] Synthesis Example 21: Preparation of Compound 334

[0251]

[0252] In Synthesis Example 1, a-3 was replaced with an equimolar amount of e-11, e-3 with an equimolar amount of e-334, and f-3 with an equimolar amount of b-3, while the other steps remained the same, yielding compound 334 (18.73 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 1039.4729 (theoretical value: 1039.4717). Theoretical elemental content (%) C 73 H 65 N3Si2: C, 84.27; H, 6.30; N, 4.04. Measured elemental content (%): C, 84.25; H, 6.28; N, 4.08.

[0253] Synthesis Example 22: Preparation of Compound 346

[0254]

[0255]

[0256] In Synthesis Example 1, e-3 was replaced with an equimolar amount of e-11, f-3 with an equimolar amount of f-267, and g-3 with an equimolar amount of g-346, while the other steps remained the same, yielding compound 346 (16.77 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 905.4156 (theoretical value: 905.4165). Theoretical elemental content (%) C 65 H 55 N3Si: C, 86.15; H, 6.12; N, 4.64. Measured elemental content (%): C, 86.18; H, 6.14; N, 4.61.

[0257] Synthesis Example 23: Preparation of Compound 362

[0258]

[0259] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-293, e-3 with an equimolar amount of e-11, and f-3 with an equimolar amount of f-362. All other steps remained the same, yielding compound 362 (15.98 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 899.4493 (theoretical value: 899.4480). Theoretical elemental content (%) C 64 H 41 D 10 N3Si: C, 85.39; H, 6.83; N, 4.67. Measured elemental content (%): C, 85.42; H, 6.81; N, 4.65.

[0260] Synthesis Example 24: Preparation of Compound 405

[0261]

[0262] In Synthesis Example 1, a-3 was replaced with an equimolar amount of e-11, e-3 was replaced with an equimolar amount of e-11, and f-3 was replaced with an equimolar amount of f-405. All other steps remained the same, yielding compound 405 (18.88 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 1033.4651 (theoretical value: 1033.4643). Theoretical elemental content (%) C 70 H 67 N3Si3: C, 81.27; H, 6.53; N, 4.06. Measured elemental content (%): C, 81.30; H, 6.55; N, 4.02.

[0263] Synthesis Example 25: Preparation of Compound 412

[0264]

[0265]

[0266] In Synthesis Example 1, e-3 was replaced with an equimolar amount of e-11, and f-3 was replaced with an equimolar amount of f-412. All other steps remained the same, yielding compound 412 (17.51 ​​g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 945.4490 (theoretical value: 945.4478). Theoretical elemental content (%) C 68 H 59 N3Si: C, 86.31; H, 6.28; N, 4.44. Measured elemental content (%): C, 86.34; H, 6.31; N, 4.42.

[0267] Synthesis Example 26: Preparation of Compound 458

[0268]

[0269] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-458, b-3 with an equimolar amount of b-458, e-3 with an equimolar amount of e-11, and f-3 with an equimolar amount of f-458, while the other steps remained the same, yielding compound 458 (20.39 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 1131.6712 (theoretical value: 1131.6702). Theoretical elemental content (%) C 81 H 73 D8N3Si: C, 85.89; H, 7.92; N, 3.71. Measured elemental content (%): C, 85.92; H, 7.88; N, 3.74.

[0270] Synthesis Example 27: Preparation of Compound 509

[0271]

[0272] In Synthesis Example 1, e-3 was replaced with an equimolar amount of e-11, and f-3 was replaced with an equimolar amount of f-509. All other steps remained the same, yielding compound 509 (17.01 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 931.4311 (theoretical value: 931.4322). Theoretical elemental content (%) C 67 H 57 N3Si: C, 86.32; H, 6.16; N, 4.51. Measured elemental content (%): C, 86.35; H, 6.14; N, 4.49.

[0273] Synthesis Example 28: Preparation of Compound 542

[0274]

[0275] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-542, e-3 with an equimolar amount of e-11, and f-3 with an equimolar amount of f-542. All other steps remained the same, yielding compound 542 (16.54 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 881.4732 (theoretical value: 881.4740). Theoretical elemental content (%) C 61 H 63 N3OSi: C, 83.04; H, 7.20; N, 4.76. Measured elemental content (%): C, 83.06; H, 7.17; N, 4.79.

[0276] Synthesis Example 29: Preparation of Compound 555

[0277]

[0278] In Synthesis Example 1, e-3 was replaced with an equimolar amount of e-555, and f-3 was replaced with an equimolar amount of f-542. All other steps remained the same, yielding compound 555 (17.40 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 927.3629 (theoretical value: 927.3645). Theoretical elemental content (%) C 66 H 49 N3OSi: C, 85.40; H, 5.32; N, 4.53. Measured elemental content (%): C, 85.38; H, 5.35; N, 4.56.

[0279] Synthesis Example 30: Preparation of Compound 573

[0280]

[0281] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-573, e-3 with an equimolar amount of e-573, and f-3 with an equimolar amount of b-3, while the other steps remained the same, yielding compound 573 (17.12 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 963.4059 (theoretical value: 963.4040). Theoretical elemental content (%) C 66 H 57 N3OSi2: C, 82.20; H, 5.96; N, 4.36. Measured elemental content (%): C, 82.24; H, 5.93; N, 4.32.

[0282] Synthesis Example 31: Preparation of Compound 578

[0283]

[0284] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-578, e-3 with an equimolar amount of e-11, and f-3 with an equimolar amount of f-542. All other steps remained the same, yielding compound 578 (18.44 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 1009.5352 (theoretical value: 1009.5366). Theoretical elemental content (%) C 71 H 71 N3OSi: C, 84.40; H, 7.08; N, 4.16. Measured elemental content (%): C, 84.37; H, 7.11; N, 4.14.

[0285] Synthesis Example 32: Preparation of Compound 587

[0286]

[0287] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-587, e-3 with an equimolar amount of a-3, and f-3 with an equimolar amount of f-542. All other steps remained the same, yielding compound 587 (18.51 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 1013.4188 (theoretical value: 1013.4197). Theoretical elemental content (%) C 70 H 59 N3OSi2: C, 82.88; H, 5.86; N, 4.14. Measured elemental content (%): C, 82.85; H, 5.84; N, 4.18.

[0288] Synthesis Example 33: Preparation of Compound 592

[0289]

[0290] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-267, e-3 with an equimolar amount of e-592, and f-3 with an equimolar amount of f-592, while the other steps remained the same, yielding compound 592 (16.17 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 897.4125 (theoretical value: 897.4114). Theoretical elemental content (%) C 63 H 55 N3OSi: C, 84.24; H, 6.17; N, 4.68. Measured elemental content (%): C, 84.26; H, 6.15; N, 4.65.

[0291] Synthesis Example 34: Preparation of Compound 612

[0292]

[0293] In Synthesis Example 1, b-3 was replaced with an equimolar amount of f-542, e-3 with an equimolar amount of e-612, and f-3 with an equimolar amount of b-3, while the other steps remained the same, yielding compound 612 (16.80 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 907.3580 (theoretical value: 907.3594). Theoretical elemental content (%) C 63 H 49 N3O2Si: C, 83.32; H, 5.44; N, 4.63. Measured elemental content (%): C, 83.35; H, 5.40; N, 4.66.

[0294] Synthesis Example 35: Preparation of Compound 621

[0295]

[0296] In Synthesis Example 1, a-3 was replaced with an equimolar amount of e-11, e-3 with an equimolar amount of a-3, and f-3 with an equimolar amount of f-542, while the other steps remained the same, yielding compound 621 (15.27 g). HPLC analysis showed a solid purity ≥ 99.96%. Mass spectrometry m / z: 813.3582 (theoretical value: 813.3571). Theoretical elemental content (%) C 54 H 51 N3OSi2: C, 79.66; H, 6.31; N, 5.16. Measured elemental content (%): C, 79.68; H, 6.29; N, 5.18.

[0297] Synthesis Example 36: Preparation of Compound 669

[0298]

[0299] Step 1: Synthesize intermediate C-542

[0300] Under nitrogen protection, e-11 (17.19 g, 75.00 mmol), f-542 (13.74 g, 75.00 mmol), and sodium tert-butoxide (10.81 g, 112.50 mmol) were dissolved in 400 mL of toluene. Pd(dppf)Cl2 (0.66 g, 0.90 mmol) was added with stirring, and the mixture was heated under reflux for 4.5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was recrystallized from ethyl acetate to give intermediate C-542 (20.88 g, 84% yield). HPLC analysis showed a solid purity ≥99.71%. Mass spectrometry m / z: 331.1381 (theoretical value: 331.1392).

[0301] Step 2: Synthesize compound 669

[0302] Under nitrogen protection, intermediates C-542 (19.89 g, 60.00 mmol), g-669 (6.30 g, 20.00 mmol), and sodium tert-butoxide (3.84 g, 40.00 mmol) were dissolved in 160 mL of toluene. Pd₂(dba)₃ (0.18 g, 0.20 mmol) and P(t-Bu)₃ (0.8 mL, 0.40 mmol, 0.5 M toluene solution) were added with stirring. The mixture of the above reactants was heated back to room temperature for 5 h. After the reaction was complete, the mixture was cooled to room temperature, water was added, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under reduced pressure. The mixture was recrystallized from toluene to give compound 669 (15.78 g, 74%). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 1065.4185 (theoretical value: 1065.4177). Theoretical element content (%) C 69 H 63 N3O3Si3: C, 77.71; H, 5.95; N, 3.94. Measured elemental content (%): C, 77.74; H, 5.91; N, 3.98.

[0303] Synthesis Example 37: Preparation of Compound 679

[0304]

[0305] In Synthesis Example 1, a-3 was replaced with an equimolar amount of e-11, e-3 with an equimolar amount of e-679, and f-3 with an equimolar amount of b-3, while the other steps remained the same, yielding compound 679 (16.69 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 889.3896 (theoretical value: 889.3884). Theoretical elemental content (%) C 60 H 55 N3OSi2: C, 80.95; H, 6.23; N, 4.72. Measured elemental content (%): C, 80.97; H, 6.20; N, 4.69.

[0306] Synthesis Example 38: Preparation of Compound 711

[0307]

[0308] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-711, e-3 with an equimolar amount of e-11, and f-3 with an equimolar amount of f-542, while the other steps remained the same, yielding compound 711 (15.41 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 855.4389 (theoretical value: 855.4367). Theoretical elemental content (%) C 59 H 33 D 14 N3OSi: C, 82.77; H, 7.18; N, 4.91. Measured elemental content (%): C, 82.79; H, 7.15; N, 4.89.

[0309] Synthesis Example 39: Preparation of Compound 724

[0310]

[0311] In Synthesis Example 1, a-3 was replaced with an equimolar amount of e-11, e-3 with an equimolar amount of e-724, and f-3 with an equimolar amount of b-3, while the other steps remained the same, yielding compound 724 (17.86 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 977.4178 (theoretical value: 977.4197). Theoretical elemental content (%) C 67 H 59 N3OSi2: C, 82.25; H, 6.08; N, 4.29. Measured elemental content (%): C, 82.29; H, 6.05; N, 4.27.

[0312] Synthesis Example 40: Preparation of Compound 742

[0313]

[0314] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-742, e-3 with an equimolar amount of e-11, and f-3 with an equimolar amount of f-742. All other steps remained the same, yielding compound 742 (17.69 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 981.5440 (theoretical value: 981.5451). Theoretical elemental content (%) C 67 H 75 N3SSi: C, 81.91; H, 7.69; N, 4.28. Measured elemental content (%): C, 81.89; H, 7.66; N, 4.26.

[0315] Synthesis Example 41: Preparation of Compound 923

[0316]

[0317] In Synthesis Example 1, a-3 was replaced with an equimolar amount of e-11, b-3 with an equimolar amount of b-923, e-3 with an equimolar amount of e-923, and f-3 with an equimolar amount of b-3. All other steps remained the same, yielding compound 923 (19.49 g). HPLC analysis showed a solid purity ≥ 99.95%. Mass spectrometry m / z: 1052.5622 (theoretical value: 1052.5609). Theoretical elemental content (%) C 72 H 76 N4Si2: C, 82.08; H, 7.27; N, 5.32. Measured elemental content (%): C, 82.11; H, 7.25; N, 5.35.

[0318] Synthesis Example 42: Preparation of Compound 974

[0319]

[0320] In Synthesis Example 1, a-3 was replaced with an equimolar amount of e-11, e-3 with an equimolar amount of e-974, and f-3 with an equimolar amount of b-3, while the other steps remained the same, yielding compound 974 (17.86 g). HPLC analysis showed a solid purity ≥ 99.92%. Mass spectrometry m / z: 964.4369 (theoretical value: 964.4357). Theoretical elemental content (%) C 66 H 60 N4Si2: C, 82.11; H, 6.26; N, 5.80. Measured elemental content (%): C, 82.14; H, 6.23; N, 5.79.

[0321] Synthesis Example 43: Preparation of Compound 1050

[0322]

[0323] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-1050, and e-3 was replaced with an equimolar amount of e-11. All other steps remained the same, yielding compound 1050 (18.29 g). HPLC analysis showed a solid purity ≥ 99.93%. Mass spectrometry m / z: 1001.4114 (theoretical value: 1001.4125). Theoretical elemental content (%) C 68 H 55 N5O2Si: C, 81.49; H, 5.53; N, 6.99. Measured elemental content (%): C, 81.51; H, 5.51; N, 6.96.

[0324] Synthesis Example 44: Preparation of Compound 1099

[0325]

[0326] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-1099, e-3 with an equimolar amount of e-11, and f-3 with an equimolar amount of f-542, while the other steps remained the same, yielding compound 1099 (16.39 g). HPLC analysis showed a solid purity ≥ 99.94%. Mass spectrometry m / z: 897.3630 (theoretical value: 897.3611). Theoretical elemental content (%) C 59 H 47 N7OSi: C, 78.90; H, 5.27; N, 10.92. Measured elemental content (%): C, 78.93; H, 5.24; N, 10.90.

[0327] Synthetic Example 45: Preparation of Compound 1139

[0328]

[0329] In Synthesis Example 1, a-3 was replaced with an equimolar amount of a-1139, e-3 with an equimolar amount of e-11, and f-3 with an equimolar amount of f-742, while the other steps remained the same, yielding compound 1139 (18.22 g). HPLC analysis showed a solid purity ≥ 99.91%. Mass spectrometry m / z: 1011.3780 (theoretical value: 1011.3791). Theoretical elemental content (%) C 69 H 53 N5SSi: C, 81.86; H, 5.28; N, 6.92. Measured elemental content (%): C, 81.88; H, 5.25; N, 6.89.

[0330] Green organic light-emitting devices (hole transport layer)

[0331] [Comparative Examples 1-2] Device Fabrication Examples:

[0332] Comparative Example 1: Fabrication of organic light-emitting devices using vacuum thermal evaporation. The experimental steps were as follows: the ITO substrate was washed three times in distilled water, ultrasonically washed for 15 minutes, and after the distilled water washing was completed, it was ultrasonically washed in sequence with solvents such as isopropanol, acetone, and methanol, dried at 120°C, and then sent to the evaporation machine.

[0333] On a prepared ITO transparent electrode, a hole injection layer 1T-NATA / 63nm, a hole transport layer HT1-1 / 100nm, a bulk m-CBP:doped Ir(ppy)2acac (94%:6% mass ratio) / 23nm were deposited by vacuum evaporation. Then, an electron transport layer TpPyPB and Liq (1:1 mass ratio) / 28nm, an electron injection layer LiF / 1nm, and a cathode Al / 130nm were deposited. The device was then sealed in a glove box, thus fabricating an organic light-emitting device. After completing the fabrication of the organic light-emitting device according to the above steps, the photoelectric performance of the device was measured. The molecular structures of the relevant materials are shown below:

[0334]

[0335] Comparative Example 2: The hole transport layer material HT1-1 in Comparative Example 1 was replaced with HT1-2, and the organic light-emitting device of Comparative Example 2 was manufactured in the same manner as in Comparative Example 1.

[0336] [Application Examples 1-31]

[0337] Application Examples 1-31: The hole transport layer material HT1-1 of the organic light-emitting device is replaced sequentially with compounds 3, 11, 25, 32, 44, 49, 152, 198, 202, 211, 261, 267, 289, 313, 346, 362, 405, 412, 458, 509, 542, 555, 578, 592, 612, 621, 669, 679, 742, 923, and 974 of the present invention, and the other steps are the same as those in Comparative Example 1.

[0338] A combined IVL testing system was used to test the luminous efficiency of organic light-emitting devices (OLEDs), comprising testing software, a computer, a Keithley K2400 digital source meter, and a PhotoResearch PR788 spectral scanning luminance meter. Lifetime testing was performed using a McScience M6000 OLED lifetime testing system. The testing environment was atmospheric, and the temperature was room temperature. The luminous characteristic test results of the obtained OLEDs are shown in Table 1. Table 1 presents the luminous characteristic test results of the OLEDs prepared by the compounds in the embodiments of this invention and the comparative materials.

[0339] [Table 1] Testing of the luminescent properties of light-emitting devices

[0340]

[0341]

[0342] Note: T97 refers to a current density of 10 mA / cm².2 Under these conditions, the time it takes for the device's brightness to decay to 97%;

[0343] As can be seen from the results in Table 1, when the star-shaped triamine compound of the present invention is applied to organic light-emitting devices as a hole transport layer material, the performance of the device is improved compared with Comparative Examples 1-2. It can be seen that silicon is the main factor affecting the device performance, and it exhibits the advantages of high luminous efficiency and long service life.

[0344] Red organic light-emitting device (second hole transport layer)

[0345] [Comparative Examples 3-4] Device Fabrication Examples:

[0346] Comparative Example 3: Fabrication of organic light-emitting devices using vacuum thermal evaporation. The experimental steps were as follows: the ITO transparent substrate was washed three times in distilled water, ultrasonically washed for 15 minutes, and after the distilled water washing was completed, it was ultrasonically washed in sequence with solvents such as isopropanol, acetone, and methanol, then dried at 120°C and sent to the evaporation machine.

[0347] The organic light-emitting device (OLED) was fabricated by depositing a hole injection layer (1T-NATA / 63nm), a hole transport layer (HT / 70nm), a second hole transport layer (HT1-1 / 30nm), a light-emitting layer (a mixture of m-CBP and Ir(2-phq)2acac (98%:2% by mass)) / 24nm, an electron transport layer (TpPyPB and Liq (1:1 by mass) / 28nm), an electron injection layer (LiF / 1nm), and a cathode (Al / 130nm). The device was then sealed in a glove box. After completing the fabrication of the OLED according to the above steps, its photoelectric properties were measured. The molecular structures of the relevant materials are shown below.

[0348]

[0349] Comparative Example 4: The second hole transport layer material HT1-1 in Comparative Example 3 was replaced with HT2-2, and the organic light-emitting device of Comparative Example 4 was manufactured in the same manner as in Comparative Example 3.

[0350] [Application Examples 32-73]

[0351] Application Examples 32-73: The material of the second hole transport layer of the organic light-emitting device is replaced sequentially with compounds 3, 11, 19, 25, 32, 44, 49, 152, 194, 198, 202, 208, 211, 261, 267, 289, 293, 313, 331, 333, 334, 346, 362, 405, 412, 458, 509, 542, 555, 573, 578, 587, 592, 612, 621, 669, 679, 711, 724, 742, 923, and 974 of the present invention. All other steps are the same as in Comparative Example 3.

[0352] A combined IVL testing system was constructed using testing software, a computer, a K2400 digital source meter manufactured by Keithley, Inc. (USA), and a PR788 spectrophotometer from PhotoResearch, Inc. (USA) to test the driving voltage and luminous efficiency of organic light-emitting devices (OLEDs). The luminous characteristics test results of the OLEDs are shown in Table 2. Table 2 presents the luminous characteristics test results of the OLEDs prepared from the compounds and comparative materials in the embodiments of this invention.

[0353] [Table 2] Testing of the luminescent properties of light-emitting devices

[0354]

[0355]

[0356] As can be seen from the results in Table 2, when the star-shaped triamine compound of the present invention is applied to organic light-emitting devices as a second hole transport layer material, compared with comparative examples 3-4, it can be seen that silicon is the main factor affecting device performance, significantly improving the luminous efficiency and lifespan of organic light-emitting devices. It is a high-performance organic light-emitting material. In particular, when one or more silane groups are introduced into Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6, the hole transport performance and thermal stability of the compound are even better.

[0357] [Comparative Examples 5-6] Device Fabrication Examples:

[0358] Comparative Example 5: Fabrication of organic light-emitting devices using vacuum thermal evaporation. The experimental steps were as follows: ITO-Ag-ITO substrate was washed three times in distilled water, ultrasonically washed for 15 minutes, and after distilled water washing, it was ultrasonically washed in sequence with solvents such as isopropanol, acetone, and methanol, then dried at 120°C and sent to the evaporation machine.

[0359] On a prepared ITO-Ag-ITO transparent electrode, a hole injection layer of 1T-NATA (63 nm), a hole transport layer of HT (100 nm), a bulk BH:doped BD (97%:3% mass ratio) (25 nm) were deposited by vacuum evaporation. Then, an electron transport layer of TpPyPB and Liq (1:1 mass ratio) (28 nm), an electron injection layer of LiF (1 nm), a cathode of Mg-Ag (19 nm), and a capping layer of CP-1 (80 nm) were deposited on the cathode. The device was then sealed in a glove box, thus fabricating an organic light-emitting device. After completing the fabrication of the organic light-emitting device according to the above steps, the photoelectric performance of the device was measured. The molecular structures of the relevant materials are shown below:

[0360]

[0361] Comparative Example 6: The cover material CP-1 in Comparative Example 5 was replaced with CP-2, and the organic light-emitting device of Comparative Example 6 was manufactured in the same manner as in Comparative Example 5.

[0362] [Application Examples 74-90]

[0363] Application Examples 74-90: The capping material of the organic light-emitting device is replaced sequentially with compounds 19, 25, 32, 152, 198, 313, 405, 555, 573, 578, 621, 669, 724, 974, 1050, 1099, and 1139 of the present invention, and all other steps are the same as in Comparative Example 5.

[0364] A combined IVL testing system was constructed using testing software, a computer, a K2400 digital source meter manufactured by Keithley, and a PR788 spectral scanning luminance meter manufactured by PhotoResearch, to test the driving voltage and luminous efficiency of organic light-emitting devices (OLEDs). The test results of the luminous characteristics of the OLEDs are shown in Table 3. Table 3 presents the luminous characteristic test results of the OLEDs prepared by the compounds prepared in the embodiments of the present invention and the comparative materials.

[0365]

[0366]

[0367] Note: T95 refers to a current density of 10 mA / cm². 2 Under certain conditions, the time it takes for the device's brightness to decay to 95%;

[0368] As can be seen from the results in Table 3, the star-shaped triamine compound of the present invention, when used as a capping material in organic light-emitting devices, can effectively improve the light extraction efficiency compared with comparative examples 5-6, thereby improving the luminous efficiency of organic light-emitting devices. It is a high-performance capping material for organic light-emitting devices.

[0369] 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 star-shaped triamine compound, characterized in that, The molecular structure is shown in Formula I-1 or Formula I-2: Wherein, one, two, three, or four of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are selected from the groups shown in formula a, and the rest are independently selected from the groups shown in formula b: Wherein, one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is selected from the group shown in formula a, meaning that Ar1, Ar2, Ar3, Ar4, Ar5, or Ar6 is selected from the group shown in formula a, wherein formula a is selected from one of the following groups: ； Two of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are selected from the group shown in formula a, meaning Ar1 and Ar2, Ar1 and Ar3, Ar1 and Ar5, Ar3 and Ar4, Ar3 and Ar5, or Ar5 and Ar6 are selected from... ; Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 are selected from groups shown in formula a, meaning Ar1, Ar2, and Ar3; Ar1, Ar2, and Ar5; Ar1, Ar3, and Ar4; Ar1, Ar3, and Ar5; Ar1, Ar5, and Ar6; Ar3, Ar4, and Ar5; or Ar3, Ar5, and Ar6 are selected from... ; Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6, four of which are selected from the group shown in formula a, refer to Ar1, Ar2, Ar3, and Ar4; Ar1, Ar2, Ar3, and Ar5; Ar1, Ar2, Ar5, and Ar6; Ar1, Ar3, Ar4, and Ar5; or Ar3, Ar4, Ar5, and Ar6 selected from... ; The R a1 The substituent is selected from hydrogen, deuterium, tritium, substituted or unsubstituted groups of the following: trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, adamantyl, phenyl, and the "substituted or unsubstituted" substituent is selected from one or more of hydrogen, deuterium, and tritium; The R a The substituent is selected, either identically or differently, from hydrogen, deuterium, tritium, or substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, phenyl, wherein the "substituted or unsubstituted" substituent is selected from one or more of hydrogen, deuterium, and tritium, or Two adjacent R a Groups bond together to form substituted or unsubstituted benzene rings; The R m Selected, either identically or differently, from one of hydrogen, deuterium, tritium, methyl, ethyl, n-propyl, n-butyl, isopropyl, and tert-butyl; said R m It can also be R mm Replaced by, R mm Selected from one or more of hydrogen, deuterium, and tritium, and when substituted by multiple substituents, the multiple substituents may be the same or different from each other; The R m1 Selected, either identically or differently, from one of hydrogen, deuterium, tritium, methyl, ethyl, n-propyl, n-butyl, isopropyl, and tert-butyl; said R m1 It can also be R mm Replaced by, R mm Selected from one or more of hydrogen, deuterium, and tritium, and when substituted by multiple substituents, the multiple substituents may be the same or different from each other; The R b The substituent is selected from hydrogen, deuterium, tritium, substituted or unsubstituted groups of the following: methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, and the "substituted or unsubstituted" substituent is selected from one or more of hydrogen, deuterium, and tritium. In the case of being substituted by multiple substituents, the multiple substituents are the same as or different from each other. The m2 is selected from 1, 2, 3 or 4; the m7 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14; The a is selected from 1, 2, or 3; the b is selected from 1, 2, 3, or 4; the c is selected from 1, 2, 3, 4, or 5; the d is selected from 1, 2, 3, 4, 5, or 6; the g is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the i is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11. R4 and R5 are independently selected from hydrogen, deuterium, tritium, or one of the following groups, substituted or unsubstituted: methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, phenyl, biphenyl, naphthyl; R6 is selected from one of the following groups, substituted or unsubstituted: phenyl, biphenyl, naphthyl; Formula b is selected from one of the following groups: The R e The same or different R is selected from one of hydrogen, deuterium, tritium, methyl, ethyl, n-propyl, n-butyl, isopropyl, and tert-butyl; wherein R e It can also be R ee Replaced by, R ee Selected from one or more of hydrogen, deuterium, and tritium; The c1 is selected from 1, 2, 3, 4, or 5; the c2 is selected from 1, 2, 3, or 4; the c3 is selected from 1, 2, or 3; the c4 is selected from 1, 2, 3, 4, 5, 6, or 7; the c5 is selected from 1 or 2; the c6 is selected from 1, 2, 3, 4, 5, or 6; the c7 is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; the c8 is selected from 1, 2, 3, 4, 5, 6, 7, or 8; and the c9 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10. The R c The same or different elements are selected from hydrogen, deuterium, tritium, halogen, trifluoromethyl, trimethylsilyl, triethylsilyl, triisopropylsilyl, tri-tert-butylsilyl, triphenylsilyl, trideuterated phenylsilyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, cyclohexyl, cyclopentyl, cyclobutyl, cyclopropyl, adamantyl, and phenyl; wherein R c It can also be R cc Replaced by, R cc Selected from one or more of hydrogen, deuterium, and tritium, and when substituted by multiple substituents, the multiple substituents may be the same or different from each other; The R c1 The same or different R is selected from one of hydrogen, deuterium, tritium, halogen, trifluoromethyl, methyl, ethyl, n-propyl, n-butyl, isopropyl, tert-butyl, and phenyl; wherein R c1 It can also be R cc Replaced by, R cc Selected from one or more of hydrogen, deuterium, and tritium, and when substituted by multiple substituents, the multiple substituents may be the same or different from each other; R1, R2, and R3 are independently selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted C1 to C6 alkyl groups; The L1, L2, L3, L4, L5, and L6 are independently selected from single bonds or one of the following groups: The R d They may be the same as or different from each other, and are selected from any one of hydrogen, deuterium, tritium, substituted or unsubstituted C1 to C6 alkyl groups; The d1 is selected from 0, 1, 2, 3 or 4; R1, R2, R3, R4, R5, R6, R d The term "substituted..." as used herein refers to a group that is monosubstituted or polysubstituted by a C1-C6 alkyl group independently selected from deuteryl, trityl, deuterated or unsubstituted groups; The condition is that at least one of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 contains one or more substituted or unsubstituted silyl groups, wherein the substituted or unsubstituted silyl group is selected from trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, and triphenylsilyl.

2. The star-shaped triamine compound according to claim 1, characterized in that, The star-shaped triamine compound satisfies one of the following conditions: i. R a1 One of them is selected from trimethylsilyl, triethylsilyl, triisopropylsilyl, and tritert-butylsilyl; ii. R c One, two, or three of them are selected from trimethylsilyl, triethylsilyl, triisopropylsilyl, tritert-butylsilyl, triphenylsilyl, and trideuterated phenylsilyl.

3. The star-shaped triamine compound according to claim 1, characterized in that, One of Ar1, Ar2, Ar3, Ar4, Ar5, and Ar6 is selected from the group shown in formula a, wherein formula a is selected from one of the following groups: The R b Selected from hydrogen, deuterium, and tritium, either the same or different; The a is selected from 1, 2, or 3; the b is selected from 1, 2, 3, or 4; the c is selected from 1, 2, 3, 4, or 5; the d is selected from 1, 2, 3, 4, 5, or 6; the e is selected from 1, 2, 3, 4, 5, 6, or 7; the g is selected from 1, 2, 3, 4, 5, 6, 7, 8, or 9; and the i is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, or 11.

4. The star-shaped triamine compound according to claim 1, characterized in that, Formula b is selected from one of the following groups: 。 5. The star-shaped triamine compound according to claim 1, characterized in that, The L1, L2, L3, L4, L5, and L6 are independently selected from single-bonded, substituted, or unsubstituted groups of the following: phenyl, wherein the substituent is one or more of deuterium and tritium, and in the case of being substituted by multiple substituents, the multiple substituents are the same as or different from each other.

6. A star-shaped triamine compound, characterized in that, The star-shaped triamine compound is selected from any of the following chemical structures: 。 7. An organic light-emitting device, comprising an anode, a cathode, and an organic layer, wherein the organic layer is located between the anode and the cathode or outside one or more electrodes of the anode and the cathode, and the organic layer includes a hole transport region, a light-emitting layer, an electron transport region, or a capping layer, characterized in that, The hole transport region and at least one of the capping layers contain any one or a combination of at least two of the star-shaped triamine compounds according to any one of claims 1 to 6.

8. An organic light-emitting device according to claim 7, characterized in that, The hole transport region includes at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, wherein the hole transport layer contains any one or a combination of at least two of the star-shaped triamine compounds according to any one of claims 1 to 6.

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