A triazine compound and an organic electroluminescence device thereof

Abstract

The application provides a triazine compound and an organic electroluminescent device thereof, and relates to the technical field of organic electroluminescent materials.The compound is a structure in which an alkylsilyl group is used as a substituent, and a fused oxazole / thiazole / imidazole is used as one of fixing groups, and is combined with an electron-deficient pyridine / pyrimidine / triazine group.The compound has high electron mobility and a high triplet energy level, and is particularly suitable for an electron transport region and a light-emitting layer material of an organic electroluminescent material.When the compound is used in an electron transport layer and a light-emitting layer of an organic electroluminescent device, the electron transport performance of the device can be effectively improved, the balance degree of hole and electron injection is enhanced, the driving voltage of the device is reduced, and the light-emitting efficiency and service life of the device are improved.

Description

Technical Field

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

[0002] Organic light-emitting diodes (OLEDs) emit light through devices made of organic light-emitting materials under the influence of an electric field or current. Compared to traditional displays, OLEDs offer advantages such as a wide viewing angle, low power consumption, and short response time, making them stand out in the display field and gradually attracting the attention and importance of researchers. Currently, OLEDs have demonstrated significant advantages and broad application prospects in the field of organic optoelectronics.

[0003] OLEDs typically employ a sandwich structure, where an organic layer is sandwiched between a cathode and anode. This organic layer is further divided into several layers: an electron injection layer (EIL), an electron transport layer (ETL), a hole blocking layer (HBL), and a light-emitting layer (EML). Under an applied electric field, electrons are generated in the cathode material and holes in the anode material. Under an external voltage, electrons and holes are injected into the organic layer from the cathode and anode, respectively. Due to the energy difference, and under the influence of the built-in electric field, electrons and holes migrate to the EML, where they bind together to form electron-hole pairs, i.e., excitons. These excitons, with higher energy, transition from the excited state to the ground state, generating photons that cause light emission.

[0004] Electron transport materials are organic semiconductor materials that enable the orderly migration of electrons under the influence of an electric field, thereby achieving electron transport. Well-known electron transport materials include Alq3, TAZ, TPBi, Bphen, and BCP. However, most electron transport materials suffer from drawbacks such as low mobility and low glass transition temperature. Furthermore, the hole mobility in hole transport materials is much higher than that in electron transport materials, preventing carrier migration from reaching equilibrium and exciton recombination from being effective, resulting in low luminous efficiency of the device. Simultaneously, the energy level mismatch between the functional layers in the device also affects its performance, thus limiting the application of electron transport materials in OLEDs. Therefore, developing electron transport materials with high electron mobility and high triplet energy levels is crucial. Summary of the Invention

[0005] To address the problems existing in the prior art, this invention provides a novel triazine compound that can effectively improve electron mobility and luminous efficiency, thereby enhancing the performance of organic electroluminescent devices. This triazine compound is represented by the following formula I.

[0006]

[0007] Wherein, X is selected from oxygen atom, sulfur atom or NR. a The R a It is selected from one of the following: hydrogen atom, deuterium atom, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0008] The ring A is selected from one of the structures shown in [Formula A-1] to [Formula A-10].

[0009]

[0010] The * indicates the loop position;

[0011] The Z that is the same or different is selected from nitrogen atoms or CR. b The R b The same or different is selected from one of the following: linking bond, hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C1-C15 alkylsilyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C2-C30 heteroaryl group;

[0012] R1 is selected from one of the following: a linking bond, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C1-C15 alkylsilyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group.

[0013] The Y is selected from nitrogen atoms or CR. d And at least one Y is selected from nitrogen atoms, wherein R d The same or different is selected from one of the following: linking bond, hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C1-C15 alkylsilyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C2-C30 heteroaryl group;

[0014] The Ar1 and Ar2, whether the same or different, are selected from one of the substituted or unsubstituted C6-C30 aryl groups and the substituted or unsubstituted C2-C30 heteroaryl groups;

[0015] The L, L1, and L2 are the same or different and are selected from one of the single-bonded, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene;

[0016] Formula I contains at least one substituted or unsubstituted C1-C15 alkylsilyl group.

[0017] The present invention also provides an organic electroluminescent device, comprising an anode, a cathode, and an organic layer, wherein the organic layer contains at least one of the triazine compounds of the present invention.

[0018] Beneficial effects:

[0019] This invention provides a silicon-containing compound with alkylsilyl groups as substituents and a fused oxazole / thiazole / imidazolium group as one of the fixing groups, combined with an electron-deficient pyridine / pyrimidine / triazine group. The fused oxazole / thiazole / imidazolium group possesses high electron mobility, and its combination with the pyridine / pyrimidine / triazine group can effectively enhance the electron transport capability of the material. Furthermore, using alkylsilyl groups as substituents, especially as substituents for the fused oxazole / thiazole / imidazolium group, can further enhance the electron transport capability of the material, thereby improving the luminescence performance of organic electroluminescent devices. Secondly, the compound of this invention possesses a high triplet energy level, making it particularly suitable as the host material for organic electroluminescent materials. When the compound of this invention is used in the emitting layer of an organic electroluminescent device, it will effectively improve the electron transport performance of the device, thereby enhancing the balance between hole and electron injection, reducing the driving voltage of the device, and improving the luminescence efficiency and lifespan of the device. Detailed Implementation

[0020] The present invention will be further illustrated below with reference to specific embodiments. It should be understood that these embodiments are for illustrative purposes only and are not intended to limit the scope of the invention. After reading the present invention, any modifications of the present invention in various equivalent forms by those skilled in the art will fall within the scope of protection claimed in this application.

[0021] 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.

[0022] In this invention, the halogen is selected from one of fluorine, chlorine, bromine, and iodine.

[0023] In this invention, 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.

[0024] For example, Can represent Can represent Can represent And so on.

[0025] In this invention, the substituents represented by "substituted or unsubstituted" include: hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, nitro groups, substituted or unsubstituted C1-C15 alkyl groups, substituted or unsubstituted C1-C15 alkylsilyl groups, substituted or unsubstituted C3-C20 cycloalkyl groups, substituted or unsubstituted C6-C30 aryl groups, substituted or unsubstituted C2-C30 heteroaryl groups, etc., but are not limited thereto; preferably, the substituents include: hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, and substituted or unsubstituted groups such as methyl, ethyl. propyl, isopropyl, butyl, tert-butyl, pentyl, isopentyl, neopentyl, methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, dimethylethylsilyl, diethylmethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, tritert-butylsilyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, camphenyl, isocamphenyl, fentanyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, anthracene, pyrene Substituents include fluorenyl, spirodifluorenyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxolinyl, phenanthrolineyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, imidazolyl, benzoimidazolyl, benzofuranyl, dibenzofuranyl, benzothiophene, dibenzothiophene, indolyl, carbazolyl, etc.; when there are multiple substituents, the multiple substituents can be the same or different, or two adjacent substituents can be connected to form a substituted or unsubstituted ring.

[0026] In this invention, "C1-C15 alkyl group" refers to a straight-chain or branched hydrocarbon group having 1 to 15 carbon atoms, preferably 1 to 10, more preferably 1 to 6. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl, 2-methylpentyl, 3-methylpentyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, heptyl, 2,2-dimethylpentane, 2,3-dimethylpentane, 3-methylhexane, 2,4-dimethylpentane, 2,2,3-trimethylbutane, 2-methylhexane, 3-ethylpentane, octyl, 2-methylheptane, 2,2-dimethylhexane, 2,2,4-trimethylpentane, 2,2,3,3-tetramethylbutane, etc., but are not limited thereto.

[0027] In this invention, "C1 to C15 alkylsilyl" refers to a silyl group having alkyl substitution with 1 to 15 carbon atoms, wherein the number of alkyl groups is 1, 2, or 3, and the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 6, and most preferably 1 to 3. Examples of the alkylsilyl group include methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, methylethylsilyl, dimethylethylsilyl, diethylmethylsilyl, tripropylsilyl, tributylsilyl, tritert-butylsilyl, dimethyltert-butylsilyl, etc., but are not limited thereto.

[0028] In this invention, "C3-C20 cycloalkyl group" refers to a cyclic saturated hydrocarbon group having 3 to 20 carbon atoms, preferably 3 to 15, more preferably 3 to 10, and most preferably 3 to 6. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornel, camphenyl, fentanyl, isocamphenyl, etc.

[0029] In this invention, "C6-C30 aryl" refers to an aromatic cyclic group having 6 to 30 carbon atoms, preferably 6 to 25, more preferably 6 to 20, and most preferably 6 to 12. Examples of the aryl group include phenyl, biphenyl, terphenyl, naphthyl, anthracene, benzo[a]anthrayl, phenanthyl, benzo[a]phenanthyl, phenatenyl, styrene, pyrene, etc. Benzyl, benzo[ It includes, but is not limited to, phenylene, fluorene, spirofluorene, benzospirodifluorene, etc.

[0030] In this invention, "C2-C30 heteroaryl" refers to an aromatic cyclic group containing heteroatoms with 2 to 30 carbon atoms, preferably 2 to 25, more preferably 2 to 20, and most preferably 2 to 12. The heteroatoms are O, S, N, Si, B, P, etc., but are not limited thereto. Examples of the heteroaryl groups include, but are not limited to, pyrroloyl, pyrazolyl, imidazolyl, triazolyl, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, naphthidyl, pteridyl, phenanthrolinel, benzoquinolinyl, benzoisoquinolinyl, indolyl, isoindolyl, benzoimidazolyl, naphthidyl, phenanthidyl, anthraquinimidazolyl, tribenzimidazolyl, pyridinylimidazolyl, pyrimidinylimidazolyl, triazinylimidazolyl, quinolinylimidazolyl, isoquinolinylimidazolyl, quinoxalinylimidazolyl, quinoxalinylimidazolyl, furanyl, benzofuranyl, dibenzofuranyl, thiophene, benzothiophene, dibenzothiophene, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, carbazole, etc.

[0031] In this invention, "C6-C30 arylene" refers to a divalent aromatic ring group having 6 to 30 carbon atoms, preferably 6 to 25, more preferably 6 to 20, and most preferably 6 to 12. Examples of the arylene include phenylene, biphenylene, terphenylene, naphthylene, phenanthrene, anthracene, triphenylene, pyrene, and so on. Fluoride, spirofluorene, etc., but not limited to these.

[0032] In this invention, the "C2-C30 heteroaryl group" refers to a divalent aromatic cyclic group containing heteroatoms with 2 to 30 carbon atoms, preferably 2 to 25, more preferably 2 to 20, and most preferably 2 to 12. The heteroatoms are O, S, N, Si, B, P, etc., but are not limited thereto. Examples of the heteroaryl group include pyridine, pyrazolidine, imidazolyl, triazolidine, pyridinidine, pyrazinidine, pyridazinidine, pyridazinidine, triazinidine, quinolinidine, isoquinolinidine, quinazolinidine, quinoxalinidine, naphthidyl, pteridinidine, phenanthroline, dibenzofuranyl, dibenzothiophene, carbazolyl, etc., but are not limited thereto.

[0033] In this invention, "two adjacent groups connecting to form a substituted or unsubstituted ring" means that two adjacent groups are connected to each other by chemical bonds and optionally aromatized to form a substituted or unsubstituted hydrocarbon ring or a substituted or unsubstituted heterocycle. The hydrocarbon ring can be an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring. The heterocycle can include an aliphatic heterocycle or an aromatic heterocycle. The aliphatic hydrocarbon ring can be a saturated aliphatic hydrocarbon ring or an unsaturated aliphatic hydrocarbon ring, and the aliphatic heterocycle can be a saturated aliphatic heterocycle or an unsaturated aliphatic heterocycle. The hydrocarbon ring and heterocycle can be monocyclic or polycyclic groups. Furthermore, the ring formed by the combination of adjacent groups can be connected to another ring to form a spirostructure. An example is shown below:

[0034]

[0035] In this invention, the rings formed by the connection can be three-membered rings, four-membered rings, five-membered rings, six-membered rings, seven-membered rings, fused rings, etc. Specific examples include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, benzene, naphthalene, phenanthrene, triphenylene, pyridine, pyrimidine, quinoline, fluorene, furan, thiophene, carbazole, etc., but are not limited thereto.

[0036] In this invention, "at least one" includes one, two, three, four, five, six, seven, eight or more.

[0037] This invention provides a triazine compound, represented by the following formula I,

[0038]

[0039] Wherein, X is selected from oxygen atom, sulfur atom or NR. a The R a It is selected from one of the following: hydrogen atom, deuterium atom, substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C1-C15 alkylsilyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl.

[0040] The ring A is selected from one of the structures shown in [Formula A-1] to [Formula A-10].

[0041]

[0042] The * indicates the loop position;

[0043] The Z that is the same or different is selected from nitrogen atoms or CR. b The R b The same or different is selected from one of the following: linking bond, hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C1-C15 alkylsilyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C2-C30 heteroaryl group;

[0044] R1 is selected from one of the following: a linking bond, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted C1-C15 alkyl group, a substituted or unsubstituted C1-C15 alkylsilyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C6-C30 aryl group, and a substituted or unsubstituted C2-C30 heteroaryl group.

[0045] The Y is selected from nitrogen atoms or CR. d And at least one Y is selected from nitrogen atoms, wherein R d The same or different is selected from one of the following: linking bond, hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C1-C15 alkylsilyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, and substituted or unsubstituted C2-C30 heteroaryl group;

[0046] The Ar1 and Ar2, whether the same or different, are selected from one of the substituted or unsubstituted C6-C30 aryl groups and the substituted or unsubstituted C2-C30 heteroaryl groups;

[0047] The L, L1, and L2 are the same or different and are selected from one of the single-bonded, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C2-C30 heteroarylene;

[0048] Formula I contains at least one substituted or unsubstituted C1 to C15 alkylsilyl group.

[0049] Preferably, the C1 to C15 alkylsilyl group is selected from silyl groups substituted with 1, 2, or 3 alkyl groups having a carbon number of 1 to 15. More preferably, the alkyl group has a carbon number of 1 to 10, further preferably 1 to 6, and most preferably 1 to 3.

[0050] Preferably, the alkylsilyl group is selected from methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, methylethylsilyl, dimethylethylsilyl, diethylmethylsilyl, tripropylsilyl, tributylsilyl, tritert-butylsilyl, and dimethyltert-butylsilyl.

[0051] Preferably, one, two, or three of the Y atoms are selected from nitrogen atoms, and the remainder are selected from CR atoms. d The R d It is selected from one of the following: linking bond, hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, substituted or unsubstituted butyl group, substituted or unsubstituted dimethylsilyl group, substituted or unsubstituted trimethylsilyl group, substituted or unsubstituted triethylsilyl group, substituted or unsubstituted cyclopropyl group, substituted or unsubstituted cyclobutyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted norbornel group, and substituted or unsubstituted camphenyl group.

[0052] Preferably, Formula I is selected from the structures shown in Formula I-1 to Formula I-5.

[0053]

[0054] One, two, or three of the Y atoms are selected from nitrogen atoms, and the remainder are selected from CR atoms. d The R dIt is selected from one of the following: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group, substituted or unsubstituted propyl group, substituted or unsubstituted butyl group, substituted or unsubstituted dimethylsilyl group, substituted or unsubstituted trimethylsilyl group, substituted or unsubstituted triethylsilyl group, substituted or unsubstituted cyclopropyl group, substituted or unsubstituted cyclobutyl group, substituted or unsubstituted cyclopentyl group, substituted or unsubstituted cyclohexyl group, substituted or unsubstituted adamantyl group, substituted or unsubstituted norbornel group, and substituted or unsubstituted camphenyl group.

[0055] More preferably, the I is selected from one of the structures shown in Formula I-6 to Formula I-10.

[0056]

[0057] Preferably, ring A is selected from one of the following structures:

[0058]

[0059]

[0060]

[0061] The R2, whether identical or different, is selected from one of the following: hydrogen atom, deuterium atom, halogen atom, cyano, methyl, deuterated methyl, ethyl, propyl, isopropyl, deuterated isopropyl, tert-butyl, deuterated tert-butyl, trifluoromethyl, trimethylsilyl, triethylsilyl, cyclopentyl, deuterated cyclopentyl, cyclohexyl, deuterated cyclohexyl, adamantyl, norbornelyl, camphenyl, phenyl, deuterated phenyl, biphenyl, deuterated biphenyl, naphthyl, deuterated naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, and quinoxalinyl.

[0062] The m1 is selected from 1 or 2; the m2 is selected from 1, 2, 3 or 4; the m3 is selected from 1, 2 or 3; and the m4 is selected from 1.

[0063] Preferably, R1 is selected from the following groups: linking bond, hydrogen atom, deuterium atom, halogen atom, cyano group, and substituted or unsubstituted groups: methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, methylsilyl, dimethylsilyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyridyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, dibenzofuranyl, diphenyl The substituent is selected from one of thiophene, carbazolyl, fluorenyl, and spirofluorenyl; the substituent in "substituted or unsubstituted" is selected from one of hydrogen atom, deuterium atom, halogen atom, cyano, methyl, isopropyl, tert-butyl, methylsilyl, dimethylsilyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, deuterated phenyl, naphthyl, pyridyl, and pyrimidinyl; when there are multiple substituents, the multiple substituents can be the same or different, or two adjacent substituents can be connected to form a substituted or unsubstituted ring.

[0064] More preferably, R1 is selected from phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, phenylenetriene, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, quinolinyl, isoquinolinyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, fluoreneyl, and spirofluoreneyl groups substituted with one, two, or three groups selected from methylsilyl, dimethylsilyl, trimethylsilyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, and tributylsilyl.

[0065] Preferably, the Ar1 and Ar2 are selected from one of the following groups:

[0066]

[0067] The E is selected from oxygen atom, sulfur atom, and NR. x or CR y The R x R y The same or different from one selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C1-C15 alkylsilyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent R groups. y They can connect to each other to form substituted or unsubstituted rings;

[0068] The R3s, whether identical or different, are selected from one of the following: hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C1-C15 alkylsilyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent R3s can be linked together to form a substituted or unsubstituted ring.

[0069] The n1 is selected from 1, 2, 3, 4 or 5; the n2 is selected from 1, 2, 3 or 4; the n3 is selected from 1, 2 or 3; the n4 is selected from 1 or 2; and the n5 is selected from 1.

[0070] Preferably, the Ar1 and Ar2 are selected from one of the following groups:

[0071]

[0072]

[0073] The R3 is the same as or different from the following groups selected from hydrogen, deuterium, halogen, cyano, substituted or unsubstituted groups: methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, methylsilyl, dimethylsilyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, norbornel, phenyl, biphenyl, terphenyl, naphthyl, anthracene, phenanthrene, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, dibenzofuranyl, dibenzothiophene. The substituent is selected from one of carbazolyl, fluorenyl, and spirofluorenyl; the substituent in "substituted or unsubstituted" is selected from one of hydrogen atom, deuterium atom, halogen atom, cyano, methyl, isopropyl, tert-butyl, methylsilyl, dimethylsilyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, deuterated phenyl, naphthyl, pyridyl, and pyrimidinyl; when there are multiple substituents, the multiple substituents can be the same or different, or two adjacent R3s can be connected to form a substituted or unsubstituted ring;

[0074] The n1 is selected from 1, 2, 3, 4 or 5; the n2 is selected from 1, 2, 3 or 4; the n3 is selected from 1, 2 or 3; the n4 is selected from 1 or 2; and the n5 is selected from 1.

[0075] Preferably, one, two, or three R3s in Ar1 are selected from methylsilyl, dimethylsilyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, and tributylsilyl.

[0076] Preferably, one, two, or three of the R3s in Ar2 are selected from methylsilyl, dimethylsilyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, and tributylsilyl.

[0077] Preferably, the L, L1, and L2, whether the same or different, are selected from single bonds or one of the following groups:

[0078]

[0079] The T that is the same or different is selected from nitrogen atoms or CR. z The R z The same or different from one selected from hydrogen atom, deuterium atom, halogen atom, cyano group, substituted or unsubstituted C1-C15 alkyl group, substituted or unsubstituted C1-C15 alkylsilyl group, substituted or unsubstituted C3-C20 cycloalkyl group, substituted or unsubstituted C6-C30 aryl group, substituted or unsubstituted C2-C30 heteroaryl group, or two adjacent R groups. z They can connect to each other to form substituted or unsubstituted rings.

[0080] Preferably, the L, L1, and L2, whether the same or different, are selected from single bonds or one of the following groups:

[0081]

[0082] k1 is selected from 0, 1, 2, 3 or 4; k2 is selected from 0, 1, 2, 3, 4, 5 or 6; k3 is selected from 0, 1, 2 or 3; k4 is selected from 0, 1 or 2.

[0083] Preferably, Formula I contains one, two, three, four, five, six, seven or eight substituted or unsubstituted C1 to C15 alkylsilyl groups.

[0084] Preferably, Formula I contains one, two, three, four, five, six, seven or eight groups selected from methylsilyl, dimethylsilyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, and tributylsilyl.

[0085] Most preferably, Formula I is selected from one of the following structures.

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

[0106]

[0107]

[0108]

[0109]

[0110] The above lists some specific chemical structures of the triazine compounds described in Formula I of this invention. However, this invention is not limited to these listed chemical structures. Any structure based on Formula I with substituents defined above should be included.

[0111] The organic electroluminescent device of the present invention includes a substrate, a cathode, an organic layer, and an anode, wherein the organic layer contains the triazine compound of the present invention.

[0112] Preferably, the organic layer includes an electron transport region located between the anode and the cathode, and the electron transport region contains the triazine compound described in this invention.

[0113] Preferably, the organic layer further includes a light-emitting layer located between the anode and the electron transport region, and the light-emitting layer contains the triazine compound described in this invention.

[0114] Preferably, the light-emitting layer comprises a host material and a dopant material, wherein the host material contains the triazine compound described in this invention.

[0115] The organic layer in the organic electroluminescent device of the present invention may include one or more of the functional layers described below, such as a hole injection layer, a hole transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer. Each functional layer may be composed of a single thin film or multiple thin films, and each thin film may contain one material or multiple materials.

[0116] The materials in each organic layer of the organic electroluminescent device mentioned above, as well as the electrode materials on both sides of the device, will be described below:

[0117] The substrate is the support for the electroluminescent device, and can be made of silicon wafers, quartz, glass plates, metal plates, plastic films or sheets.

[0118] The anode material is typically preferred to be a material with a high work function, which facilitates the injection of holes into the organic layer. Specific examples of anode materials that can be used in this invention include: metals, such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides, such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides, such as ZnO:Al or SnO2:Sb; conductive polymers, such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0119] The highest occupied molecular orbital (HOMO) of the hole-injected material is preferably between the work function of the anolyte and the HOMO of the surrounding organic material layer. Specific examples of hole-injected materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, and conductive polymers based on polyaniline and polythiophene, and may also include compounds capable of p-doping.

[0120] Hole transport materials are materials capable of receiving holes from the anode or hole injection layer and transporting them to the emissive layer, with materials exhibiting high hole mobility being particularly suitable. Specific examples include, but are not limited to, small molecule materials such as arylamine-based organic materials, aromatic amine derivatives, carbazole derivatives, stilbene derivatives, triphenyldiamine derivatives, styrene compounds, and butadiene compounds, as well as polymeric materials such as poly(p-phenylene) derivatives, polyaniline and its derivatives, polythiophene and its derivatives, polyvinylcarbazole and its derivatives, and polysilane and its derivatives.

[0121] An electron blocking layer is positioned between the hole transport layer and the light-emitting layer. As an electron blocking material, it needs to possess both good hole transport capability and electron blocking capability to effectively transport holes and restrict electrons. Aromatic amine derivatives, carbazole derivatives, etc., can be used for the electron blocking layer. Examples include: N,N-bis([1,1'-biphenyl]-4-yl)-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-amine, N-(4'-(9H-carbazole-9-yl)-[1,1'-biphenyl]-4-N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluorene-2-amine, and N,N'-bis(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPD), etc.

[0122] The luminescent layer can emit red, green, or blue light and can be formed from phosphorescent or fluorescent materials. The luminescent material is a material capable of emitting light in the visible light region by receiving holes and electrons from the hole transport layer and electron transport layer, respectively, and by combining the holes with the electrons, and is preferably a material with favorable quantum efficiency for fluorescence or phosphorescence. Specific examples include, but are not limited to, 8-hydroxyquinoline aluminum ligand (Alq3); carbazole-based compounds, dipolystyrene-based compounds, 10-hydroxybenzoquinoline-metal compounds, benzothiazole-based and benzimidazole-based compounds, polymers based on poly(p-phenylenevinylene) (PPV), spirocyclic compounds, polyfluorene, fluorene, etc.

[0123] The main materials of the luminescent layer include fused aromatic ring derivatives and heterocyclic compounds. Specifically, fused aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited to these.

[0124] Doping materials used as the light-emitting layer include metal complexes such as iridium complexes, osmium complexes, and platinum complexes, but are not limited to these.

[0125] Hole-blocking materials have the function of blocking holes within the light-emitting layer, including heterocyclic compounds such as imidazole compounds and phenanthroline compounds. Examples of such hole-blocking materials include, but are not limited to, the materials described below, such as 1,3,5-tris(N-phenyl-2-benzimidazole)benzene (TPBi) and 4,7-diphenyl-1,10-phenanthroline (Bphen), but are not limited thereto.

[0126] Electron transport materials are materials that advantageously receive electrons from the cathode and transport them to the emitting layer; materials with high electron mobility are suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavonoid-metal complexes, etc.

[0127] The electron injection layer can promote electron injection. Preferred electron injection materials are compounds that possess electron transport capabilities, exhibit an electron injection effect from the cathode, demonstrate excellent electron injection effects on the luminescent layer or luminescent material, prevent excitons generated in the luminescent layer from migrating to the hole injection layer, and possess excellent thin film formation capabilities. Specific examples include fluorenones, anthraquinone dimethane, biphenylquinone, thiamethane dioxide, diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal complexes, nitrogen-containing five-membered ring derivatives, etc., but are not limited to these.

[0128] As cathode materials, materials with low work functions are generally preferred to facilitate electron injection into the organic layer. Specific examples of cathode materials include: metals, such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, or alloys thereof; multilayer materials, such as LiF / Al, LiO2 / Al, etc., but are not limited to these.

[0129] In this invention, each layer of the organic electroluminescent device can be fabricated using dry film deposition methods, such as vacuum evaporation, sputtering, plasma deposition, and ion plating; or wet film deposition methods, such as inkjet printing, nozzle printing, slot coating, spin coating, dip coating, and flow coating.

[0130] 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.

[0131] The following embodiments illustrate the present invention in more detail; however, the embodiments described below are merely examples of this specification, and the scope of this specification is not limited to these embodiments.

[0132] Synthesis Examples

[0133] There are no particular limitations on the preparation method of the triazine compounds represented by Formula I of this invention, and conventional methods well known to those skilled in the art can be used. For example, carbon-carbon coupling reactions, etc. The triazine compounds represented by Formula I of this invention can be prepared, for example, by the synthetic route shown below.

[0134]

[0135]

[0136] X1, whether the same or different, is selected from F, Cl, Br, or I; X2 is selected from...

[0137] Raw materials and reagents: All raw materials and reagents used in this invention are of reagent purity. This invention does not impose any particular limitations on the raw materials or reagents used in the following synthesis examples; they can be commercially available products or prepared using methods well-known to those skilled in the art.

[0138] Instruments: (1) G2-Si quadrupole tandem time-of-flight high-resolution mass spectrometer (Waters Corporation, UK); (2) Vario EL cube organic elemental analyzer (Elementar Corporation, Germany); (3) Bruker-510 nuclear magnetic resonance spectrometer (Bruker Corporation, Germany).

[0139] Synthesis Example 1: Preparation of Intermediate a-106

[0140]

[0141] Preparation of intermediate B-106:

[0142] Add A-106 (58.29 g, 310.00 mmol), m-106 (65.97 g, 370.00 mmol), sodium cyanide (15.19 g, 310.00 mmol), and DMF (1550 mL) to a reaction flask. Stir the mixture at 100 °C for 3 hours. After the reaction is complete, cool the reaction mixture to room temperature, add distilled water, extract with ethyl acetate, separate the organic layer, dry the organic layer with anhydrous magnesium sulfate, filter, concentrate the solvent by vacuum distillation, cool to crystallize, filter, and recrystallize the obtained solid with toluene to give intermediate B-106 (81.59 g, yield 76%); HPLC purity ≥99.69%. Mass spectrometry m / z: 345.0172 (theoretical value: 345.0185).

[0143] Preparation of intermediate C-106:

[0144] Under nitrogen protection, B-106 (79.65 g, 230.00 mmol), n-106 (46.10 g, 250.00 mmol), Pd(PPh3)4 (10.63 g, 9.20 mmol), Na2CO3 (60.94 g, 575.00 mmol), and 1080 mL of a toluene / ethanol / water (4:1:1) mixed solvent were added to a reaction flask, and the mixture was stirred at 140 °C for 4 hours. After the reaction was completed, the mixture was cooled to room temperature and washed with distilled water and methanol to obtain intermediate C-106 (79.36 g, yield 85%); HPLC purity ≥99.72%. Mass spectrometry m / z: 405.0940 (theoretical value: 405.0952).

[0145] Preparation of intermediate D-106:

[0146] C-106 (77.13 g, 190.00 mmol), (methoxymethyl)triphenylphosphine chloride (97.70 g, 285.00 mmol), and 1000 mL of tetrahydrofuran were added to a reaction flask. The mixture was stirred and then cooled to below 0 °C. Potassium tert-butoxide (1 M THF solution, 285 mL) was slowly added dropwise to the mixture. After the addition was complete, the temperature of the mixture was slowly increased, and the mixture was stirred at room temperature for 4.5 hours. The reaction was quenched with water, and then extracted with ethyl acetate. The organic layer was washed with water and dried with anhydrous sodium sulfate. The mixture was filtered, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. After filtration, the intermediate D-106 (67.62 g, 82% yield) was purified by column chromatography (petroleum ether: dichloromethane = 10:1); HPLC purity ≥99.75%. Mass spectrometry m / z: 433.1279 (theoretical value: 433.1265).

[0147] Preparation of intermediate a-106:

[0148] D-106 (65.10 g, 150.00 mmol), Eaton reagent (7.7 wt% phosphorus pentoxide methanesulfonic acid solution) (1.26 g, 5.28 mmol), and chlorobenzene (600 mL) were added to the reaction flask, and the mixture was refluxed for 5 hours. After the reaction was completed, the mixture was cooled to room temperature and then extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the solvent was concentrated by vacuum distillation. Crystals were then precipitated by cooling, filtered, and recrystallized from toluene to give intermediate a-106 (48.24 g, 80% yield); HPLC purity ≥99.78%. Mass spectrometry m / z: 401.1018 (theoretical value: 401.1003).

[0149] Synthesis Example 2: Preparation of Intermediate a-142

[0150]

[0151] Following the same preparation method as intermediate a-106 in Synthesis Example 1, m-106 was replaced with an equimolar amount of m-142 to obtain intermediate a-142 (48.84 g), with an HPLC purity ≥99.76%. Mass spectrometry m / z: 401.1015 (theoretical value: 401.1003).

[0152] Synthesis Example 3: Preparation of Intermediate a-147

[0153]

[0154] Following the same preparation method as intermediate a-106 in Synthesis Example 1, m-106 was replaced with an equimolar amount of m-147, and n-106 was replaced with an equimolar amount of n-147 to obtain intermediate a-147 (47.75 g), with an HPLC purity ≥99.78%. Mass spectrometry m / z: 402.0943 (theoretical value: 402.0955).

[0155] Synthesis Example 4: Preparation of Intermediate a-149

[0156]

[0157] Following the same preparation method as intermediate a-106 in Synthesis Example 1, n-106 was replaced with an equimolar amount of n-147 to obtain intermediate a-149 (48.24 g), with an HPLC purity ≥99.75%. Mass spectrometry m / z: 401.1013 (theoretical value: 401.1003).

[0158] Synthesis Example 5: Preparation of Intermediate a-151

[0159]

[0160] Following the same preparation method as intermediate a-106 in Synthesis Example 1, m-106 was replaced with an equimolar amount of m-151 to obtain intermediate a-151 (54.50 g), with an HPLC purity ≥99.77%. Mass spectrometry m / z: 477.1305 (theoretical value: 477.1316).

[0161] Synthesis Example 6: Preparation of Intermediate a-190

[0162]

[0163] Following the same preparation method as intermediate a-106 in Synthesis Example 1, m-106 was replaced with an equimolar amount of m-190 to obtain intermediate a-190 (52.89 g), with an HPLC purity ≥99.80%. Mass spectrometry m / z: 451.1144 (theoretical value: 451.1159).

[0164] Synthesis Example 7: Preparation of Intermediate a-200

[0165]

[0166] Following the same preparation method as intermediate a-106 in Synthesis Example 1, m-106 was replaced with an equimolar amount of m-200 to obtain intermediate a-200 (49.56 g), with an HPLC purity ≥99.74%. Mass spectrometry m / z: 402.0967 (theoretical value: 402.0955).

[0167] Synthesis Example 8: Preparation of Intermediate a-359

[0168]

[0169] Following the same preparation method as intermediate a-106 in Synthesis Example 1, A-106 was replaced with an equimolar amount of A-359 to obtain intermediate a-359 (48.24 g), with an HPLC purity ≥99.76%. Mass spectrometry m / z: 401.1018 (theoretical value: 401.1003).

[0170] Synthesis Example 9: Preparation of Intermediate a-363

[0171]

[0172] Following the same preparation method as intermediate a-106 in Synthesis Example 1, A-106 was replaced with an equimolar amount of A-359, and m-106 was replaced with an equimolar amount of m-363, yielding intermediate a-363 ​​(46.80 g) with an HPLC purity ≥99.81%. Mass spectrometry m / z: 415.1145 (theoretical value: 415.1159).

[0173] Synthesis Example 10: Preparation of Intermediate a-364

[0174]

[0175] Following the same preparation method as intermediate a-106 in Synthesis Example 1, A-106 was replaced with an equimolar amount of A-359, and n-106 was replaced with an equimolar amount of n-147 to obtain intermediate a-364 (48.67 g), with an HPLC purity ≥99.75%. Mass spectrometry m / z: 401.1017 (theoretical value: 401.1003).

[0176] Synthesis Example 11: Preparation of Intermediate a-482

[0177]

[0178] Following the same preparation method as intermediate a-106 in Synthesis Example 1, A-106 was replaced with an equimolar amount of A-482, and n-106 was replaced with an equimolar amount of n-147, yielding intermediate a-482 (47.65 g) with an HPLC purity ≥99.73%. Mass spectrometry m / z: 417.0760 (theoretical value: 417.0774).

[0179] Synthesis Example 12: Preparation of Intermediate a-494

[0180]

[0181] Following the same preparation method as intermediate a-106 in Synthesis Example 1, A-106 was replaced with an equimolar amount of A-482 to obtain intermediate a-494 (46.40 g), with an HPLC purity ≥99.79%. Mass spectrometry m / z: 417.0786 (theoretical value: 417.0774).

[0182] Synthesis Example 13: Preparation of Intermediate a-606

[0183]

[0184] Following the same preparation method as intermediate a-106 in Synthesis Example 1, A-106 was replaced with an equimolar amount of A-606, m-106 was replaced with an equimolar amount of m-606, and n-106 was replaced with an equimolar amount of n-147, yielding intermediate a-606 (49.69 g) with an HPLC purity ≥99.75%. Mass spectrometry m / z: 459.1259 (theoretical value: 459.1244).

[0185] Synthesis Example 14: Preparation of Intermediate a-619

[0186]

[0187] Following the same preparation method as intermediate a-106 in Synthesis Example 1, A-106 was replaced with an equimolar amount of A-606 to obtain intermediate a-619 (47.03 g), with an HPLC purity ≥99.77%. Mass spectrometry m / z: 417.0762 (theoretical value: 417.0774).

[0188] Synthesis Example 15: Preparation of Compound 2

[0189]

[0190] Synthesis of intermediate I-2:

[0191] Under nitrogen protection, starting material a-2 (35.66 g, 110.00 mmol), pinacol diboronate (29.20 g, 115.00 mmol), K2CO3 (30.41 g, 220.00 mmol), and Pd(PPh3)4 (1.27 g, 1.10 mmol) were added to DMF (475 mL). The mixture of the above reactants was heated under reflux for 4 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The obtained solid was recrystallized from ethyl acetate and dried to obtain intermediate I-2 (33.49 g, yield 82%). HPLC purity ≥99.76%. Mass spectrometry m / z: 371.1681 (theoretical value: 371.1693).

[0192] Synthesis of intermediate II-2:

[0193] Under nitrogen protection, I-2 (20.42 g, 55.00 mmol), b-2 (11.44 g, 50.00 mmol), CH3COOK (9.81 g, 100.00 mmol), Pd(dppf)Cl2 (0.37 g, 0.50 mmol), and THF (250 mL) were added to the reaction flask, and the mixture was reacted under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the filter cake was obtained. The filter cake was recrystallized from toluene / ethanol at a ratio of 10:1 to give intermediate II-2 (15.73 g, yield 80%); HPLC purity ≥99.88%. Mass spectrometry m / z: 392.0245 (theoretical value: 392.0232).

[0194] Synthesis of compound 2:

[0195] Under nitrogen protection, II-2 (13.76 g, 35.00 mmol), c-2 (20.72 g, 75.00 mmol), Na2CO3 (6.89 g, 65.00 mmol), Pd(OAc)2 (0.09 g, 0.40 mmol), P(t-Bu)3 (0.23 g, 0.80 mmol), and THF (140 mL) were added to a reaction flask, and the mixture was reacted under reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene to give compound 2 (14.56 g, yield 67%); HPLC purity ≥99.95%. Mass spectrometry m / z: 620.2441 (theoretical value: 620.2428). Theoretical elemental content (%) C 38 H 36N4OSi2: C, 73.51; H, 5.84; N, 9.02. Measured elemental content (%): C, 73.54; H, 5.80; N, 9.07.

[0196] Synthesis Example 16: Preparation of Compound 38

[0197]

[0198] Synthesis of intermediate I-38:

[0199] Under nitrogen protection, starting material a-38 (22.40 g, 110.00 mmol), pinacol diboronate (29.20 g, 115.00 mmol), K₂CO₃ (30.41 g, 220.00 mmol), and Pd(PPh₃)₄ (1.27 g, 1.10 mmol) were added to DMF (470 mL). The mixture of the above reactants was heated under reflux for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The obtained solid was recrystallized from ethyl acetate and dried to obtain intermediate I-38 (26.95 g, yield 83%). HPLC purity ≥99.72%. Mass spectrometry m / z: 295.1369 (theoretical value: 295.1380).

[0200] Synthesis of intermediate II-38:

[0201] Under nitrogen protection, I-38 (22.14 g, 75.00 mmol), b-38 (22.42 g, 70.00 mmol), CH3COOK (13.74 g, 140.00 mmol), Pd(dppf)Cl2 (0.51 g, 0.70 mmol), and THF (340 mL) were added to the reaction flask, and the mixture was reacted under reflux for 5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the filter cake was obtained. The filter cake was recrystallized from toluene / ethanol at a ratio of 10:1 to obtain intermediate II-38 (20.50 g, yield 81%); HPLC purity ≥99.85%. Mass spectrometry m / z: 359.9402 (theoretical value: 359.9414).

[0202] Synthesis of intermediate III-38:

[0203] Under nitrogen protection, II-38 (18.08 g, 50.00 mmol), c-2 (15.19 g, 55.00 mmol), CH3COOK (10.80 g, 110.00 mmol), Pd(dppf)Cl2 (0.37 g, 0.50 mmol), and THF (325 mL) were added to the reaction flask, and the mixture was reacted under reflux for 7 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered to obtain a filter cake, and recrystallized from the filter cake with toluene / ethanol at a ratio of 5:1 to obtain intermediate III-38 (17.02 g, yield 79%); HPLC purity ≥99.89%. Mass spectrometry m / z: 430.1030 (theoretical value: 430.1017).

[0204] Synthesis of compound 38:

[0205] Under nitrogen protection, III-38 (15.08 g, 35.00 mmol), d-38 (10.45 g, 40.00 mmol), Na₂CO₃ (7.63 g, 72.00 mmol), Pd(OAc)₂ (0.08 g, 0.35 mmol), P(t-Bu)₃ (0.20 g, 0.70 mmol), and THF (130 mL) were added to a reaction flask, and the reaction was carried out under reflux for 8.5 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO₄, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene to give compound 38 (12.98, yield 70%); HPLC purity ≥99.94%. Mass spectrometry m / z: 529.2302 (theoretical value: 529.2315). Theoretical elemental content (%) C 33 H 19 D7N4OSi: C, 74.82; H, 6.28; N, 10.58. Measured elemental content (%): C, 74.87; H, 6.24; N, 10.61.

[0206] Synthesis Example 17: Preparation of Compound 106

[0207]

[0208] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-106, c-2 with an equimolar amount of c-106, and d-38 with an equimolar amount of d-106, yielding compound 106 (14.65 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 674.2515 (theoretical value: 674.2502). Theoretical elemental content (%) C 45 H 34N4OSi: C, 80.09; H, 5.08; N, 8.30. Measured elemental content (%): C, 80.13; H, 5.05; N, 8.26.

[0209] Synthesis Example 18: Preparation of Compound 107

[0210]

[0211] Synthesis of intermediate I-106:

[0212] Under nitrogen protection, starting material a-106 (44.22 g, 110.00 mmol), pinacol diboronate (29.20 g, 115.00 mmol), K2CO3 (30.41 g, 220.00 mmol), and Pd(PPh3)4 (1.27 g, 1.10 mmol) were added to DMF (475 mL). The mixture of the above reactants was heated under reflux for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. After standing and separation, the organic layer was collected, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated by vacuum distillation. The obtained solid was recrystallized from ethyl acetate and dried to obtain intermediate I-106 (46.68 g, yield 86%). HPLC purity ≥99.75%. Mass spectrometry m / z: 493.2234 (theoretical value: 493.2245).

[0213] Synthesis of intermediate II-107:

[0214] I-106 (45.89 g, 93.00 mmol), e-107 (17.23 g, 90.00 mmol), sodium carbonate (19.08 g, 180.00 mmol), and 360 mL of toluene / ethanol / water (2:1:1) mixed solvent were added to the reaction flask. After purging the air three times with nitrogen, Pd(PPh3)4 (1.04 g, 0.90 mmol) was added to the reaction flask, and the reaction was carried out under reflux for 4.5 hours. After the reaction was completed, the mixture was cooled to room temperature, filtered, and the filter cake was obtained. The filter cake was recrystallized from toluene / ethanol at a ratio of 5:1 to obtain intermediate II-107 (36.14 g, yield 84%); HPLC purity ≥99.85%. Mass spectrometry m / z: 477.1328 (theoretical value: 477.1316).

[0215] Synthesis of intermediate III-107:

[0216] Under nitrogen protection, II-107 (31.07 g, 65.00 mmol), pinacol diborate (17.78 g, 70.00 mmol), potassium acetate (12.76 g, 130.00 mmol), and DMF (400 mL) were added to the reaction flask. After purging the air with nitrogen three times, Pd(dppf)Cl2 (0.51 g, 0.70 mmol) was added. The mixture was heated and stirred for 6 hours. After the reaction was completed, it was cooled to room temperature, distilled water was added, and the mixture was extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate, the solvent was concentrated by vacuum distillation, and crystals were precipitated by cooling. The crystals were filtered and recrystallized from toluene to obtain intermediate III-107 (30.36 g, yield 82%); HPLC purity ≥99.88%. Mass spectrometry m / z: 569.2571 (theoretical value: 569.2558).

[0217] Synthesis of intermediate IV-107:

[0218] Under nitrogen protection, III-107 (30.19 g, 53.00 mmol), b-2 (11.44 g, 50.00 mmol), K2CO3 (13.82 g, 100.00 mmol), Pd(OAc)2 (0.11 g, 0.50 mmol), P(t-Bu)3 (0.16 g, 0.55 mmol), and THF (200 mL) were added to a reaction flask, and the mixture was reacted under reflux for 7.5 hours. 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 MgSO4, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene to give intermediate IV-107 (23.07 g, yield 78%); HPLC purity ≥99.89%. Mass spectrometry m / z: 590.1082 (theoretical value: 590.1096).

[0219] Preparation of compound 107:

[0220] Under nitrogen protection, IV-107 (20.70 g, 35.00 mmol), c-106 (15.31 g, 75.00 mmol), Na₂CO₃ (13.35 g, 126.00 mmol), Pd(OAc)₂ (0.09 g, 0.40 mmol), P(t-Bu)₃ (0.23 g, 0.80 mmol), and THF (140 mL) were added to a reaction flask, and the reaction was carried out under reflux for 9 hours. After the reaction was completed, the mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO₄, the solvent was removed under reduced pressure, and the mixture was recrystallized from toluene to give compound 107 (15.35 g, 65% yield); HPLC purity ≥99.96%. Mass spectrometry m / z: 674.2515 (theoretical value: 674.2502). Theoretical elemental content (%) C45 H 34 N4OSi: C, 80.09; H, 5.08; N, 8.30. Measured elemental content (%): C, 80.14; H, 5.04; N, 8.27.

[0221] Synthetic Example 19: Preparation of Compound 139

[0222]

[0223] Following the same preparation method as Compound 2 in Synthesis Example 15, a-2 was replaced with an equimolar amount of a-139, b-2 with an equimolar amount of b-139, and c-2 with an equimolar amount of c-139, yielding Compound 139 (16.71 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 769.2932 (theoretical value: 769.2945). Theoretical elemental content (%) C 51 H 43 N3OSi2: C, 79.54; H, 5.63; N, 5.46. Measured elemental content (%): C, 79.55; H, 5.60; N, 5.48.

[0224] Synthesis Example 20: Preparation of Compound 142

[0225]

[0226] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-142, c-2 with an equimolar amount of c-142, and d-38 with an equimolar amount of d-142, yielding compound 142 (17.98 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 855.3430 (theoretical value: 855.3442). Theoretical elemental content (%) C 59 H 37 D5N4OSi: C, 82.77; H, 5.53; N, 6.54. Measured elemental content (%): C, 82.82; H, 5.49; N, 6.57.

[0227] Synthesis Example 21: Preparation of Compound 143

[0228]

[0229] Following the same preparation method as compound 2 in Synthesis Example 15, a-2 was replaced with an equimolar amount of a-106, and c-2 was replaced with an equimolar amount of c-143, yielding compound 143 (17.06 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 798.2804 (theoretical value: 798.2815). Theoretical elemental content (%) C55 H 38 N4OSi: C, 82.68; H, 4.79; N, 7.01. Measured elemental content (%): C, 82.63; H, 4.82; N, 6.97.

[0230] Synthesis Example 22: Preparation of Compound 147

[0231]

[0232] Following the same preparation method as Compound 2 in Synthesis Example 15, a-2 was replaced with an equimolar amount of a-147, and c-2 was replaced with an equimolar amount of c-147 to obtain Compound 147 (16.84 g), with an HPLC purity ≥99.94%. Mass spectrometry m / z: 751.2781 (theoretical value: 751.2767). Theoretical elemental content (%) C 50 H 37 N5OSi: C, 79.86; H, 4.96; N, 9.31. Measured elemental content (%): C, 79.91; H, 4.92; N, 9.28.

[0233] Synthesis Example 23: Preparation of Compound 149

[0234]

[0235] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-149, c-2 with an equimolar amount of c-149, and d-38 with an equimolar amount of d-149, yielding compound 149 (18.94 g) with an HPLC purity ≥99.92%. Mass spectrometry m / z: 858.3741 (theoretical value: 858.3754). Theoretical elemental content (%) C 59 H 50 N4OSi: C, 82.48; H, 5.87; N, 6.52. Measured elemental content (%): C, 82.53; H, 5.90; N, 6.49.

[0236] Synthesis Example 24: Preparation of Compound 151

[0237]

[0238] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-151, c-2 with an equimolar amount of c-151, and d-38 with an equimolar amount of d-151, yielding compound 151 (15.88 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 743.2340 (theoretical value: 743.2328). Theoretical elemental content (%) C45 H 32 F3N5OSi: C, 72.66; H, 4.34; N, 9.42. Measured elemental content (%): C, 72.71; H, 4.30; N, 9.46.

[0239] Synthesis Example 25: Preparation of Compound 152

[0240]

[0241] Following the same preparation method as compound 2 in Synthesis Example 15, a-2 was replaced with an equimolar amount of a-106, b-2 with an equimolar amount of b-152, and c-2 with an equimolar amount of c-152, yielding compound 152 (17.35 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 750.2801 (theoretical value: 750.2815). Theoretical elemental content (%) C 51 H 38 N4OSi: C, 81.57; H, 5.10; N, 7.46. Measured elemental content (%): C, 81.62; H, 5.06; N, 7.50.

[0242] Synthesis Example 26: Preparation of Compound 153

[0243]

[0244] Following the same preparation method as compound 107 in Synthesis Example 18, e-107 was replaced with an equimolar amount of e-153, and c-106 was replaced with an equimolar amount of c-143, yielding compound 153 (19.11 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 852.3021 (theoretical value: 852.3033). Theoretical elemental content (%) C 57 H 40 N6OSi: C, 80.25; H, 4.73; N, 9.85. Measured elemental content (%): C, 80.30; H, 4.69; N, 9.88.

[0245] Synthesis Example 27: Preparation of Compound 160

[0246]

[0247] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-149, b-38 with an equimolar amount of b-160, c-2 with an equimolar amount of c-160, and d-38 with an equimolar amount of d-160, yielding compound 160 (17.35 g) with an HPLC purity ≥99.92%. Mass spectrometry m / z: 825.2912 (theoretical value: 825.2924). Theoretical elemental content (%) C 56 H 39 N5OSi: C, 81.43; H, 4.76; N, 8.48. Measured elemental content (%): C, 81.48; H, 4.72; N, 8.51.

[0248] Synthesis Example 28: Preparation of Compound 161

[0249]

[0250] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-106, c-2 with an equimolar amount of c-106, and d-38 with an equimolar amount of d-161, yielding compound 161 (15.67 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 688.2284 (theoretical value: 688.2295). Theoretical elemental content (%) C 45 H 32 N4O2Si: C, 78.46; H, 4.68; N, 8.13. Measured elemental content (%): C, 78.51; H, 4.64; N, 8.10.

[0251] Synthesis Example 29: Preparation of Compound 190

[0252]

[0253] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-190, c-2 with an equimolar amount of c-106, and d-38 with an equimolar amount of d-190, yielding compound 190 (16.65 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 754.2211 (theoretical value: 754.2223). Theoretical elemental content (%) C 49 H 34 N4OSSi: C, 77.95; H, 4.54; N, 7.42. Measured elemental content (%): C, 77.90; H, 4.58; N, 7.39.

[0254] Synthesis Example 30: Preparation of Compound 191

[0255]

[0256] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-106, c-2 with an equimolar amount of c-191, and d-38 with an equimolar amount of d-191, yielding compound 191 (16.33 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 764.2960 (theoretical value: 764.2971). Theoretical elemental content (%) C 52 H 40 N4OSi: C, 81.64; H, 5.27; N, 7.32. Measured elemental content (%): C, 81.59; H, 5.31; N, 7.29.

[0257] Synthesis Example 31: Preparation of Compound 197

[0258]

[0259] Following the same preparation method as compound 2 in Synthesis Example 15, a-2 was replaced with an equimolar amount of a-106, b-2 with an equimolar amount of b-152, and c-2 with an equimolar amount of c-197, yielding compound 197 (18.03 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 830.2702 (theoretical value: 830.2713). Theoretical elemental content (%) C 55 H 38 N4O3Si: C, 79.49; H, 4.61; N, 6.74. Measured elemental content (%): C, 79.54; H, 4.57; N, 6.77.

[0260] Synthesis Example 32: Preparation of Compound 200

[0261]

[0262] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-200, c-2 with an equimolar amount of c-106, and d-38 with an equimolar amount of d-200, yielding compound 200 (16.41 g) with an HPLC purity ≥99.91%. Mass spectrometry m / z: 732.2115 (theoretical value: 732.2128). Theoretical elemental content (%) C 45 H 32 N6OSSi: C, 73.74; H, 4.40; N, 11.47. Measured elemental content (%): C, 73.78; H, 4.36; N, 11.50.

[0263] Synthesis Example 33: Preparation of Compound 203

[0264]

[0265] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-106, c-2 with an equimolar amount of c-203, and d-38 with an equimolar amount of d-203, yielding compound 203 (17.37 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 826.3717 (theoretical value: 826.3703). Theoretical elemental content (%) C 55 H 50 N4O2Si: C, 79.87; H, 6.09; N, 6.77. Measured elemental content (%): C, 79.92; H, 6.06; N, 6.81.

[0266] Synthesis Example 34: Preparation of Compound 219

[0267]

[0268] Following the same preparation method as compound 2 in Synthesis Example 15, a-2 was replaced with an equimolar amount of a-106, b-2 with an equimolar amount of b-152, and c-2 with an equimolar amount of c-219, yielding compound 219 (15.87 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 676.2421 (theoretical value: 676.2407). Theoretical elemental content (%) C 43 H 32 N6OSi: C, 76.30; H, 4.77; N, 12.42. Measured elemental content (%): C, 76.25; H, 4.81; N, 12.39.

[0269] Synthesis Example 35: Preparation of Compound 244

[0270]

[0271] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-244, c-2 with an equimolar amount of c-244, and d-38 with an equimolar amount of d-244, yielding compound 244 (17.58 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 796.3041 (theoretical value: 796.3054). Theoretical elemental content (%) C 52 H 44 N4OSi2: C, 78.35; H, 5.56; N, 7.03. Measured elemental content (%): C, 78.30; H, 5.60; N, 7.00.

[0272] Synthesis Example 36: Preparation of Compound 314

[0273]

[0274] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-314, c-2 with an equimolar amount of c-314, and d-38 with an equimolar amount of d-314, yielding compound 314 (17.66 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 826.3141 (theoretical value: 826.3128). Theoretical elemental content (%) C 57 H 42 N4OSi: C, 82.78; H, 5.12; N, 6.77. Measured elemental content (%): C, 82.83; H, 5.09; N, 6.73.

[0275] Synthesis Example 37: Preparation of Compound 359

[0276]

[0277] Following the same preparation method as compound 2 in Synthesis Example 15, a-2 was replaced with an equimolar amount of a-359, and c-2 was replaced with an equimolar amount of c-359, yielding compound 359 (14.92 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 608.2804 (theoretical value: 608.2817). Theoretical elemental content (%) C 39 H 20 D 10 N4OSi: C, 76.94; H, 6.62; N, 9.20. Measured elemental content (%): C, 76.89; H, 6.58; N, 9.23.

[0278] Synthesis Example 38: Preparation of Compound 361

[0279]

[0280] Following the same preparation method as compound 107 in Synthesis Example 18, a-106 was replaced with an equimolar amount of a-359, e-107 with an equimolar amount of e-361, and c-106 with an equimolar amount of c-191, yielding compound 361 (18.72 g) with an HPLC purity ≥99.97%. Mass spectrometry m / z: 774.2802 (theoretical value: 774.2815). Theoretical elemental content (%) C 53 H 38 N4OSi: C, 82.14; H, 4.94; N, 7.23. Measured elemental content (%): C, 82.19; H, 4.91; N, 7.19.

[0281] Synthesis Example 39: Preparation of Compound 363

[0282]

[0283] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-363, c-2 with an equimolar amount of c-363, and d-38 with an equimolar amount of d-363, yielding compound 363 (17.12 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 788.2960 (theoretical value: 788.2971). Theoretical elemental content (%) C 54 H 40 N4OSi: C, 82.20; H, 5.11; N, 7.10. Measured elemental content (%): C, 82.25; H, 5.07; N, 7.13.

[0284] Synthesis Example 40: Preparation of Compound 364

[0285]

[0286] Following the same preparation method as compound 107 in Synthesis Example 18, a-106 was replaced with an equimolar amount of a-364, e-107 with an equimolar amount of e-364, b-2 with an equimolar amount of b-152, and c-106 with an equimolar amount of c-364, yielding compound 364 (16.16 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 678.2743 (theoretical value: 678.2753). Theoretical elemental content (%) C 45 H 30 D4N4OSi: C, 79.61; H, 5.64; N, 8.25. Measured elemental content (%): C, 79.56; H, 5.60; N, 8.28.

[0287] Synthesis Example 41: Preparation of Compound 365

[0288]

[0289] Following the same preparation method as compound 2 in Synthesis Example 15, a-2 was replaced with an equimolar amount of a-364, b-2 with an equimolar amount of b-152, and c-2 with an equimolar amount of c-365, yielding compound 365 (17.91 g) with an HPLC purity ≥99.92%. Mass spectrometry m / z: 852.3046 (theoretical value: 852.3033). Theoretical elemental content (%) C 57 H 40N6OSi: C, 80.25; H, 4.73; N, 9.85. Measured elemental content (%): C, 80.20; H, 4.77; N, 9.82.

[0290] Synthesis Example 42: Preparation of Compound 370

[0291]

[0292] Following the same preparation method as compound 2 in Synthesis Example 15, a-2 was replaced with an equimolar amount of a-359, and c-2 was replaced with an equimolar amount of c-370, yielding compound 370 (17.45 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 778.2414 (theoretical value: 778.2400). Theoretical elemental content (%) C 51 H 34 N4O3Si: C, 78.64; H, 4.40; N, 7.19. Measured elemental content (%): C, 78.59; H, 4.36; N, 7.22.

[0293] Synthesis Example 43: Preparation of Compound 371

[0294]

[0295] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-371, b-38 with an equimolar amount of c-371, c-2 with an equimolar amount of c-371, and d-38 with an equimolar amount of d-371, yielding compound 371 (16.63 g) with an HPLC purity ≥99.91%. Mass spectrometry m / z: 730.2753 (theoretical value: 730.2764). Theoretical elemental content (%) C 48 H 38 N4O2Si: C, 78.87; H, 5.24; N, 7.67. Measured elemental content (%): C, 78.92; H, 5.20; N, 7.64.

[0296] Synthesis Example 44: Preparation of Compound 375

[0297]

[0298] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-359, and d-38 was replaced with an equimolar amount of c-197, yielding compound 375 (16.55 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 787.2787 (theoretical value: 787.2799). Theoretical elemental content (%) C 49 H 41N5O2Si2: C, 74.68; H, 5.24; N, 8.89. Measured elemental content (%): C, 74.73; H, 5.20; N, 8.92.

[0299] Synthesis Example 45: Preparation of Compound 376

[0300]

[0301] Following the same preparation method as compound 2 in Synthesis Example 15, a-2 was replaced with an equimolar amount of a-359, and c-2 was replaced with an equimolar amount of c-376, yielding compound 376 (18.43 g) with an HPLC purity ≥99.93%. Mass spectrometry m / z: 862.2245 (theoretical value: 862.2256). Theoretical elemental content (%) C 55 H 38 N4OS2Si: C, 76.54; H, 4.44; N, 6.49. Measured elemental content (%): C, 76.49; H, 4.48; N, 6.46.

[0302] Synthesis Example 46: Preparation of Compound 377

[0303]

[0304] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-364, c-2 with an equimolar amount of c-377, and d-38 with an equimolar amount of d-377, yielding compound 377 (17.47 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 791.2840 (theoretical value: 791.2829). Theoretical elemental content (%) C 51 H 37 N7OSi: C, 77.34; H, 4.71; N, 12.38. Measured elemental content (%): C, 77.29; H, 4.75; N, 12.35.

[0305] Synthesis Example 47: Preparation of Compound 386

[0306]

[0307] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-386, b-38 with an equimolar amount of b-160, c-2 with an equimolar amount of c-106, and d-38 with an equimolar amount of c-2, yielding compound 386 (15.42 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 647.2380 (theoretical value: 647.2393). Theoretical elemental content (%) C 44H 33 N3OSi: C, 81.57; H, 5.13; N, 6.49. Measured elemental content (%): C, 81.62; H, 5.09; N, 6.46.

[0308] Synthesis Example 48: Preparation of Compound 459

[0309]

[0310] Following the same preparation method as Compound 2 in Synthesis Example 15, a-2 was replaced with an equimolar amount of a-459, and c-2 was replaced with an equimolar amount of c-459, yielding Compound 459 (18.17 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 836.2837 (theoretical value: 836.2825). Theoretical elemental content (%) C 54 H 44 N4SSi2: C, 77.47; H, 5.30; N, 6.69. Measured elemental content (%): C, 77.52; H, 5.26; N, 6.72.

[0311] Synthesis Example 49: Preparation of Compound 482

[0312]

[0313] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-482, c-2 with an equimolar amount of c-482, and d-38 with an equimolar amount of d-482, yielding compound 482 (17.58 g) with an HPLC purity ≥99.98%. Mass spectrometry m / z: 765.2369 (theoretical value: 765.2382). Theoretical elemental content (%) C 50 H 35 N5SSi: C, 78.40; H, 4.61; N, 9.14. Measured elemental content (%): C, 78.45; H, 4.57; N, 9.18.

[0314] Synthesis Example 50: Preparation of Compound 494

[0315]

[0316] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-494, c-2 with an equimolar amount of c-106, and d-38 with an equimolar amount of d-494, yielding compound 494 (15.79 g) with an HPLC purity ≥99.92%. Mass spectrometry m / z: 704.2078 (theoretical value: 704.2066). Theoretical elemental content (%) C 45 H32 N4OSSi: C, 76.67; H, 4.58; N, 7.95. Measured elemental content (%): C, 76.72; H, 4.54; N, 7.98.

[0317] Synthesis Example 51: Preparation of Compound 588

[0318]

[0319] Following the same preparation method as Compound 2 in Synthesis Example 15, a-2 was replaced with an equimolar amount of a-588, and c-2 was replaced with an equimolar amount of c-588, yielding Compound 588 (16.11 g) with an HPLC purity ≥99.95%. Mass spectrometry m / z: 686.2371 (theoretical value: 686.2356). Theoretical elemental content (%) C 42 H 38 N4SSi2: C, 73.43; H, 5.58; N, 8.16. Measured elemental content (%): C, 73.38; H, 5.62; N, 8.19.

[0320] Synthesis Example 52: Preparation of Compound 606

[0321]

[0322] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-606, c-2 with an equimolar amount of c-606, and d-38 with an equimolar amount of d-606, yielding compound 606 (21.46 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 972.2722 (theoretical value: 972.2741). Theoretical elemental content (%) C 60 H 41 F5N4SSi: C, 74.05; H, 4.25; N, 5.76. Measured elemental content (%): C, 74.08; H, 4.21; N, 5.72.

[0323] Synthesis Example 53: Preparation of Compound 619

[0324]

[0325] Following the same preparation method as compound 107 in Synthesis Example 18, a-106 was replaced with an equimolar amount of a-619, e-107 with an equimolar amount of e-619, b-2 with an equimolar amount of b-152, and c-106 with an equimolar amount of c-619, yielding compound 619 (19.84 g) with an HPLC purity ≥99.96%. Mass spectrometry m / z: 871.2450 (theoretical value: 871.2437). Theoretical elemental content (%) C 56 H 37 N5O2SSi: C, 77.13; H, 4.28; N, 8.03. Measured elemental content (%): C, 77.08; H, 4.31; N, 8.07.

[0326] Synthesis Example 54: Preparation of Compound 675

[0327]

[0328] Following the same preparation method as compound 38 in Synthesis Example 16, a-38 was replaced with an equimolar amount of a-675, c-2 with an equimolar amount of c-675, and d-38 with an equimolar amount of d-314, yielding compound 675 (18.46 g) with an HPLC purity ≥99.94%. Mass spectrometry m / z: 805.2683 (theoretical value: 805.2695). Theoretical elemental content (%) C 53 H 39 N5SSi: C, 78.97; H, 4.88; N, 8.69. Measured elemental content (%): C, 78.95; H, 4.84; N, 8.66.

[0329] Device Examples

[0330] Substrate treatment: Transparent ITO glass was used as the substrate material for device fabrication. It was first ultrasonically treated with a 5% ITO cleaning solution for 30 minutes, followed by ultrasonic washing with distilled water (twice), acetone (twice), and isopropanol (twice). Finally, the ITO glass was stored in isopropanol. Before each use, the surface of the ITO glass was carefully wiped with acetone and isopropanol cotton balls, rinsed with isopropanol, dried, and then plasma-treated for 5 minutes before use.

[0331] Example 1: Hole injection layer m-MTDATA (thickness 10nm), hole transport layer HT1 (thickness 80nm), light emission layer BBCQ:(piq)2Ir(acac)=9:1 (mass ratio) (thickness 30nm), electron transport layer compound 2 (thickness 35nm), electron injection layer LiF (thickness 0.8nm), and cathode Al (thickness 130nm) were sequentially vacuum-deposited on an ITO anode.

[0332] Examples 2-40: The organic electroluminescent device was prepared according to the method in Example 1, except that compound 2 was replaced by compounds 38, 106, 107, 139, 142, 143, 147, 149, 151, 152, 153, 160, 161, 190, 191, 197, 200, 203, 219, 244, 314, 359, 361, 363, 364, 365, 370, 371, 375, 376, 377, 386, 459, 482, 494, 588, 606, 619, and 675.

[0333] Comparative Examples 1-3: The organic electroluminescent device was prepared according to the method of Example 1, except that compound L, compound M, and compound N were used to replace compound 2, respectively.

[0334] Example 41: Hole injection layer m-MTDATA (thickness 10 nm), hole transport layer HT1 (thickness 80 nm), light emission layer BBCQ:(piq)2Ir(acac)=9:1 (mass ratio) (thickness 30 nm), hole blocking layer compound 2 (thickness 5 nm), electron transport layer ET1 (thickness 35 nm), electron injection layer LiF (thickness 0.8 nm), and cathode Al (thickness 130 nm) were sequentially vacuum-deposited on an ITO anode.

[0335] Examples 42-55: The organic electroluminescent device was prepared according to the method of Example 41, except that compound 2 was replaced by compounds 106, 107, 142, 143, 152, 160, 161, 191, 197, 203, 314, 359, 365, and 377.

[0336] Comparative Examples 4-6: The organic electroluminescent device was prepared according to the method of Example 41, except that compound L, compound M, and compound N were used to replace compound 2.

[0337] Example 56: Hole injection layer F4-TCNQ (thickness 10nm), hole transport layer HT2 (thickness 120nm), light-emitting layer RH1:compound 106:RD1 = 48:48:4 (mass ratio) (thickness 30nm), electron transport layer ET2 (thickness 30nm), electron injection layer LiF (thickness 1nm), and cathode Al (thickness 150nm) were sequentially vacuum-deposited on an ITO anode.

[0338] Examples 57-65: The organic electroluminescent device was prepared according to the method of Example 56, except that compound 106 was replaced by compounds 107, 149, 190, 219, 244, 361, 364, 370, and 375.

[0339] Comparative Examples 7-8: The organic electroluminescent device was prepared according to the method of Example 56, except that compound M and compound N were used instead of compound 106.

[0340] The molecular formulas of the relevant materials are shown below:

[0341]

[0342]

[0343] Test Method: A combined IVL test system was constructed using test software, a computer, a Keithley K2400 digital source meter, and a Photo Research PR788 spectral scanning luminance meter to test the driving voltage and luminous efficiency of organic light-emitting diodes (OLEDs). Lifetime testing employed a McScience M6000 OLED lifetime testing system to measure the time it took for the OLED's brightness to decay to 96%. The test environment was ambient air at room temperature and a current density of 10 mA / cm². 2 The test results are shown in Table 1:

[0344] Table 1. Test data on the luminescence characteristics of organic electroluminescent devices.

[0345]

[0346]

[0347]

[0348] As shown in Table 1, when the triazine compounds of the present invention are used as electron transport layers, hole blocking layers and light-emitting layers, the devices exhibit excellent performance, specifically lower driving voltage, higher luminous efficiency and longer lifespan.

[0349] The above description of the disclosed embodiments enables those skilled in the art to make or use the invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the general principles defined herein may be implemented in other embodiments without departing from the spirit or scope of the invention. Therefore, the invention is not to be limited to the embodiments shown herein, but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims

1. A triazine compound, characterized in that, Represented by the following equation I-1, Wherein, X is selected from oxygen atom, sulfur atom or NR. a The R a Selected from one of substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl; the substituent in "substituted or unsubstituted" is selected from a deuterium atom; The ring A is selected from one of the structures shown below. The R2 atoms, whether identical or different, are selected from hydrogen atoms or deuterium atoms; m1 is selected from 1 or 2; m2 is selected from 1, 2, 3 or 4; The R1 is selected from the following groups: phenyl, biphenyl, naphthyl, and pyridyl, which are substituted by a linking bond and are replaced by a trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, or tributylsilyl; or selected from the following groups: phenyl, biphenyl, naphthyl, and pyridyl, which are substituted or unsubstituted by a deuterium atom. One, two, or three of the Y atoms are selected from nitrogen atoms, and the remainder are selected from CR atoms. d The R d Selected from either hydrogen or deuterium atoms; The Ar1 and Ar2 are selected from one of the following groups. The E is selected from oxygen atoms and sulfur atoms; The R3 atoms, whether identical or different, are selected from hydrogen atoms or deuterium atoms; The R 3a The same or different ones are selected from one of the hydrogen atoms or deuterium atoms; or two adjacent R atoms. 3a They can be linked together to form deuterated or unsubstituted benzene rings; The R 3b The same or different groups are selected from hydrogen atoms, deuterium atoms, halogen atoms, cyano groups, and substituted or unsubstituted groups of the following: methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, tributylsilyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl; the substituent in "substituted or unsubstituted groups of the following: methyl, ethyl, propyl, isopropyl, butyl, and tert-butyl" is selected from deuterium atoms and halogens; the substituent in "substituted or unsubstituted groups of the following: trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, and tributylsilyl" is selected from deuterium atoms; The R 3c The same or different are selected from one of hydrogen atom, deuterium atom, and phenyl; The n1 is selected from 1, 2, 3, 4, or 5; the n2 is selected from 1, 2, 3, or 4; the n3 is selected from 1, 2, or 3; the n4 is selected from 1 or 2; the n5 is selected from 1. The L is selected from a single bond or one of the following groups: The L1 and L2, whether identical or different, are selected from single bonds or one of the following groups. The k1 is selected from 0, 1, 2, 3 or 4; Formula I-1 contains one or two groups selected from trimethylsilyl, triethylsilyl, tripropylsilyl, triisopropylsilyl, and tributylsilyl.

2. The triazine compound according to claim 1, characterized in that, The ring A is selected from one of the structures shown below.

3. The triazine compound according to claim 1, characterized in that, R1 is selected from the following groups: phenyl, biphenyl, naphthyl, and pyridyl, which are either substituted or unsubstituted by a trimethylsilyl, triethylsilyl, or a linking group.

4. The triazine compound according to claim 1, characterized in that, The Ar1 and Ar2 are selected from one of the following groups.

5. The triazine compound according to claim 1, characterized in that, The L is selected from a single bond or one of the following groups: The L1 and L2, whether identical or different, are selected from single bonds or one of the following groups.

6. A triazine compound, characterized in that, The triazine compounds are selected from at least one of the structures shown below.

7. An organic electroluminescent device, comprising a substrate, an anode, a cathode, and an organic layer, characterized in that, The organic layer contains at least one of the triazine compounds according to any one of claims 1 to 6.

8. The organic electroluminescent device according to claim 7, wherein the organic layer includes an electron transport region, characterized in that, The electron transport region is located between the anode and the cathode, and the electron transport region contains at least one of the triazine compounds according to any one of claims 1 to 6.

9. The organic electroluminescent device according to claim 7, wherein the organic layer further comprises a light-emitting layer, characterized in that, The light-emitting layer is located between the anode and the electron transport region, and the light-emitting layer contains at least one of the triazine compounds according to any one of claims 1 to 6.

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