Triazine-containing organic compound and organic electroluminescent device

Abstract

The application relates to the field of organic photoelectric materials, in particular to a triazine-containing organic compound and an organic electroluminescent device. The application develops a triazine-containing organic compound as shown in a general formula (I), the compound has excellent electron transport capacity and structural stability by selecting and optimizing the connecting units and connecting sites in the structure of the compound, the compound can realize effective charge transmission and effectively improve the light-emitting efficiency of a device when being applied in a light-emitting layer in combination with a hole transport type host material.

Description

Technical Field

[0001] This invention relates to the field of organic optoelectronic materials, and more particularly to an organic compound containing triazine and an organic electroluminescent device. Background Technology

[0002] OLED (Organic Light-Emitting Diode) refers to a display technology in which organic semiconductor materials emit light through carrier injection and recombination under the drive of an electric field. It has advantages such as high brightness, high contrast, and high color saturation. It is the third generation of display technology based on electroluminescence in the display and lighting fields, following CRT picture tubes and LCD liquid crystal displays.

[0003] OLEDs generally consist of an anode, a cathode, and multiple layers of organic thin films deposited between the anode and cathode. These organic functional layers are typically categorized as a hole injection layer (HIL), a hole transport layer (HTL), an emissive layer (EML), an electron transport layer (ETL), and an electron injection layer (EIL). The transport layer's primary function is to transport charge carriers to ensure normal device operation. The injection layer optimizes the interface properties between the electrode and the organic layer and reduces the charge injection barrier, thereby lowering the startup voltage and improving device brightness. In the emissive layer, holes and electrons recombine to form excitons, which then transition from a high-energy state to a low-energy state, emitting photons (visible light). Therefore, the structural design and combination of the materials in each functional layer have a significant impact on the performance of OLED devices.

[0004] Currently, the emissive layer materials of OLED devices mainly employ host-guest doping, utilizing the combination of host and guest materials to facilitate the transport of holes and electrons, thereby achieving efficient utilization of exciton energy and improving device lifetime and efficiency. Therefore, the host material plays a crucial role in organic light-emitting devices (OLEDs). However, existing devices still suffer from problems such as carrier transport imbalance and insufficient device efficiency, severely limiting their application. Therefore, designing and developing a new generation of emissive layer host materials with better performance to further improve the efficiency of OLED devices remains a pressing issue for those skilled in the art. Summary of the Invention

[0005] To address the aforementioned problems in existing technologies, this invention develops a novel triazine-containing organic compound. By selecting and optimizing the connecting units and connecting sites in the compound structure, the compound exhibits excellent electron transport capability and structural stability. When combined with a hole transport host material and applied to the light-emitting layer, it can achieve effective charge transport and effectively improve the luminous efficiency of the device.

[0006] This invention provides an organic compound containing triazine, having a structure as shown in general formula (I):

[0007] (I)

[0008] in:

[0009] R1 is selected from pyridinyl groups that are unsubstituted or substituted with one or more deuterium (-D);

[0010] m1 is selected from 0 or 1; m2 is selected from 0 or 1; m1 + m2 is greater than or equal to 1;

[0011] Y is selected from O or S;

[0012] L1 and L2 are independently selected from single bonds, unsubstituted bonds, or bonds containing one or more substituents R. 0 Substituted aromatic groups having 6-20 carbon atoms; or unsubstituted or with one or more substituents R. 0 Substituted heteroaromatic groups having 5-20 ring atoms;

[0013] Ar1 and Ar2 are independently selected from unsubstituted or substituted groups R. 0 Substituted aromatic groups having 6-20 carbon atoms; or unsubstituted or substituted with one or more substituents R. 0 Substituted heteroaromatic groups having 5-20 ring atoms;

[0014] R 0 Each occurrence is independently selected from one or more combinations of -D, halogen, cyano, nitro, straight-chain alkyl with 1-10 carbon atoms, branched alkyl with 3-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, aromatic group with 6-20 carbon atoms, and heteroaromatic group with 5-20 cyclic atoms.

[0015] Accordingly, the present invention also provides an organic electroluminescent device comprising a cathode, an anode, and a light-emitting layer located between the cathode and the anode, wherein the light-emitting layer comprises a triazine-containing organic compound as described above.

[0016] Compared with the prior art, the significant advantages of this invention are: this invention develops a compound as shown in general formula (I), and by selecting and optimizing the connecting units and connecting sites in the compound structure, the compound possesses a large conjugated system and a suitable energy level structure; in particular, by... Introducing unsubstituted or deuterated electron-withdrawing pyridyl groups into the light-emitting layer can enhance the electron transport capability of organic compounds, effectively increase their molecular weight, and improve their molecular configuration and structural stability. When combined with hole-transporting host materials in the light-emitting layer, it can achieve efficient charge transport and significantly improve the luminous efficiency of the device. Attached Figure Description

[0017] Figure 1 Here is the mass spectrum of compound (144).

[0018] Figure 2 Here is the mass spectrum of compound (239). Detailed Implementation

[0019] The embodiments described in this invention are merely some, not all, of the embodiments described herein. All other embodiments obtained by those skilled in the art based on the embodiments described herein without inventive effort are within the scope of protection of this application. Furthermore, it should be understood that the specific embodiments described herein are for illustrative and explanatory purposes only and are not intended to limit this application.

[0020] In the description of this application, the term "comprising" means "including but not limited to," and the term "a plurality of" means "two or more." Various embodiments of this application may exist in the form of a range. It should be understood that the description in the form of a range is merely for convenience and brevity and should not be construed as a hard limitation on the scope of this application. Therefore, it should be considered that the range description has specifically disclosed all possible sub-ranges and single numerical values ​​within that range. For example, it should be considered that the range description from 1 to 6 has specifically disclosed sub-ranges such as from 1 to 3, from 1 to 4, from 1 to 5, from 2 to 4, from 2 to 6, from 3 to 6, etc., and single numbers within the range, such as 1, 2, 3, 4, 5, and 6, regardless of the range.

[0021] The terms "and / or," "or / and," and "and / or" as used herein include any one of two or more of the related listed items, as well as any and all combinations of the related listed items. These arbitrary and all combinations include any two related listed items, any more related listed items, or a combination of all related listed items. It should be noted that when at least three items are connected by at least two conjunctions selected from "and / or," "or / and," and "and / or," it should be understood that in this application, the technical solution undoubtedly includes technical solutions connected by "logical AND," and also undoubtedly includes technical solutions connected by "logical OR." For example, "A and / or B" includes three parallel solutions: A, B, and A+B. For example, the technical solution of "A, and / or, B, and / or, C, and / or, D" includes any one of A, B, C, and D (that is, a technical solution that is connected by "logical OR"), as well as any and all combinations of A, B, C, and D, that is, combinations of any two or three of A, B, C, and D, and also combinations of all four of A, B, C, and D (that is, a technical solution that is connected by "logical AND").

[0022] In this invention, "substitution" means that one or more hydrogen atoms in the substituent are replaced by the substituent.

[0023] In this invention, when the same substituent appears multiple times, it can be independently selected from different groups. If the general formula contains multiple R, then R can be independently selected from different groups.

[0024] In this invention, when no linking site is specified in the group, it indicates that any possible linking site in the group can be used as the linking site. In this invention, the single bond connecting the substituents penetrates the corresponding ring, indicating that the substituent can be linked to any position on the ring, for example... R is attached to any substituted site on the benzene ring. For example... It can be represented as , or .

[0025] In this invention, when the same group contains multiple substituents with the same symbol, the substituents can be the same as or different from each other, for example... The six Rs on the benzene ring can be the same or different from each other.

[0026] The halogens mentioned in this invention refer to fluorine, chlorine, bromine, and iodine.

[0027] In this invention, "substituted or unsubstituted" means that the functional group described after the term may contain substituents or may not contain substituents.

[0028] In this invention, "ring atom number" refers to the number of atoms in the ring-forming atoms of a structural compound (e.g., monocyclic compound, fused-ring compound, cross-linked compound, carbocyclic compound, heterocyclic compound) obtained by atomic bonding to form a ring. When the ring is substituted by a substituent, the atoms contained in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below unless otherwise specified. In aromatic groups, the ring atom number is the same as the carbon atom number; in heteroaromatic groups, the ring atom number is the carbon atom number plus the heteroatom number; for example, the ring atom number of a benzene ring is 6, the ring atom number of a naphthalene ring is 10, the ring atom number of a quinoline is 10, and the ring atom number of a dibenzofuran group is 13.

[0029] In this invention, "aromatic group" refers to any optional functional group or substituent derived from an aromatic carbon ring. The aromatic group can be a monocyclic aryl (e.g., phenyl) or a polycyclic aryl; in other words, the aromatic group can be a monocyclic aromatic group, a fused-ring aromatic group, two or more monocyclic aromatic groups conjugated by carbon-carbon bonds, a monocyclic aromatic group and a fused-ring aromatic group conjugated by carbon-carbon bonds, or two or more fused-ring aromatic groups conjugated by carbon-carbon bonds. That is, unless otherwise stated, two or more aromatic groups conjugated by carbon-carbon bonds can also be considered as the aromatic group of this application. Preferably, the aromatic group is selected from aromatic groups having 6-30 carbon atoms; further, it is selected from aromatic groups having 6-20 carbon atoms; further, it is selected from aromatic groups having 6-10 carbon atoms; the aromatic group includes, but is not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthraceneyl, phenanthrene, fluoranyl, triphenylene, pyrene, perylene, tetraphenyl, fluorenyl, dinaphthylphenyl, acenaphthyl, and their derivatives.

[0030] In this invention, a "heteroaromatic group" refers to a heteroaromatic ring or its derivative containing one, two, three, four, five, six or more heteroatoms, wherein the heteroatoms can be at least one of B, O, N, P, Si, Se and S. The heteroaromatic group can be a monocyclic heteroaryl or a polycyclic heteroaryl; in other words, the heteroaromatic group can be a single heteroaromatic ring system or a system of multiple heteroaromatic rings conjugated by carbon-carbon bonds, and any heteroaromatic ring system is a heteroaromatic monocyclic ring or a heteroaromatic fused ring. Preferably, the heteroaromatic group is selected from heteroaromatic groups having 5-30 ring atoms; further, it is selected from heteroaromatic groups having 5-20 ring atoms; further, it is selected from heteroaromatic groups having 5-10 ring atoms. Heteroaromatic groups include, but are not limited to: thiophene, furanyl, pyrrolyl, diazolyl, triazolyl, imidazolyl, pyridinyl, bipyridinyl, pyrimidinyl, triazinyl, acridineyl, pyridazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridinylpyrimidinyl, pyridinylpyrazinyl, benzothiophene, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrol, thienopyrrol, thienopyrrol, furanol, furanol, thienofuranyl, benzoisoxazolyl, benzoisothiazolyl, benzoimidazolyl, o-diazonyl, phenanthridine, primidyl, quinazolinone, dibenzothiophene, dibenzofuranyl, carbazole and their derivatives.

[0031] In this invention, the number of carbon atoms in the straight-chain alkyl group can be 1 to 20, 1 to 16, 1 to 10, or 1 to 6. Non-limiting examples of straight-chain alkyl groups include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, and -C. 10 H 21The number of carbon atoms in a branched alkyl group can be 3 to 20, 3 to 16, 3 to 10, or 3 to 6. Non-limiting examples of branched alkyl groups include: isopropyl, branched alkyl groups containing 4 carbon atoms, branched alkyl groups containing 5 carbon atoms, branched alkyl groups containing 6 carbon atoms, branched alkyl groups containing 7 carbon atoms, branched alkyl groups containing 8 carbon atoms, branched alkyl groups containing 9 carbon atoms, and branched alkyl groups containing 10 carbon atoms. The number of carbon atoms in a cyclic alkyl group can be 3 to 20, 3 to 16, 3 to 10, or 3 to 6. Non-limiting examples of cyclic alkyl groups include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl.

[0032] In this invention, when no linking site is specified in the group, it means that any linkable site in the group is selected as the linking site.

[0033] In this invention, the phrase "independently selected" means that when one or more groups appear simultaneously and in multiple places in the compound, they are all independently selected and can be the same or different.

[0034] In describing the structural elements of the present invention, the terms "comprising" or "including" or similar terms used in the present invention mean that the device or material preceding the word covers the device or material listed after the word and its equivalents, but does not exclude other devices or materials.

[0035] The terms “combinations thereof,” “any combination thereof,” “combination of groups,” and “combination” used in this invention include all suitable combinations of any two or more groups listed.

[0036] In this invention, terms such as "further," "even more," and "particularly" are used for descriptive purposes and to indicate differences in content, but should not be construed as limiting the scope of protection of this invention.

[0037] In this invention, "optionally," "optionally," and "optional" mean that they are optional, that is, they are selected from either "with" or "without." If multiple "options" appear in a technical solution, unless otherwise specified and there are no contradictions or mutual constraints, each "option" is independent.

[0038] The first aspect of the present invention provides an organic compound containing triazine, having a structure as shown in general formula (I):

[0039] (I)

[0040] in:

[0041] R1 is selected from pyridinyl groups that are unsubstituted or substituted with one or more deuterium (-D);

[0042] m1 is selected from 0 or 1; m2 is selected from 0 or 1; m1 + m2 is greater than or equal to 1;

[0043] Y is selected from O or S;

[0044] L1 and L2 are independently selected from single bonds, unsubstituted bonds, or bonds containing one or more substituents R. 0 Substituted aromatic groups having 6-20 carbon atoms; or unsubstituted or with one or more substituents R. 0 Substituted heteroaromatic groups having 5-20 ring atoms;

[0045] Ar1 and Ar2 are independently selected from unsubstituted or substituted groups R. 0 Substituted aromatic groups having 6-20 carbon atoms; or unsubstituted or substituted with one or more substituents R. 0 Substituted heteroaromatic groups having 5-20 ring atoms;

[0046] R 0 Each occurrence is independently selected from one or more combinations of -D, halogen, cyano, nitro, straight-chain alkyl with 1-10 carbon atoms, straight-chain alkyl with 3-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, aromatic group with 6-20 carbon atoms, and heteroaromatic group with 5-20 cyclic atoms.

[0047] Furthermore, the triazine-containing organic compound has a structure as shown in any of the general formulas (II-1)-(II-6):

[0048] .

[0049] In an alternative embodiment, R1 is selected from any of the following groups:

[0050] ;

[0051] Where: * indicates a connection site.

[0052] In an alternative embodiment, Y is selected from O.

[0053] In another alternative embodiment, Y is selected from S.

[0054] In an alternative embodiment, L1 and L2 are independently selected from single bonds, unsubstituted bonds, or bonds with one or more substituents R. 0 Substituted aromatic groups having 6-12 carbon atoms.

[0055] Furthermore, L1 and L2 are independently selected from single bonds or any of the following groups:

[0056] ;

[0057] Where: m3 is selected from 0, 1, 2, 3 or 4; m4 is selected from 0, 1, 2, 3, 4, 5 or 6.

[0058] In an alternative embodiment, Ar1 and Ar2 are independently selected from unsubstituted or substituted by one or more substituents R. 0 The substituted aromatic group having 6-12 carbon atoms, or unsubstituted or substituted with one or more substituents R 0 Substituted heteroaromatic groups having 5-12 ring atoms.

[0059] In an optional embodiment, Ar1 and Ar2 are independently selected from any of the following groups:

[0060] ;

[0061] Where: m5 is selected from 0, 1, 2, 3, 4 or 5; m6 is selected from 0, 1, 2, 3 or 4; m7 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

[0062] Furthermore, the R 0 Each occurrence is independently selected from one or a combination of at least two of the following: -D, -F, -Cl, cyano, nitro, unsubstituted or -D-substituted methyl, unsubstituted or -D-substituted ethyl, unsubstituted or -D-substituted n-propyl, unsubstituted or -D-substituted isopropyl, unsubstituted or -D-substituted n-butyl, unsubstituted or -D-substituted tert-butyl, unsubstituted or -D-substituted cyclohexyl, unsubstituted or -D-substituted adamantyl, unsubstituted or -D-substituted phenyl, unsubstituted or -D-substituted biphenyl, unsubstituted or -D-substituted naphthyl, and unsubstituted or -D-substituted pyridyl.

[0063] In one specific embodiment, the triazine-containing organic compound of the present invention has any of the following structures, but is not limited thereto:

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073]

[0074]

[0075]

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[0078]

[0079]

[0080]

[0081]

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104]

[0105]

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[0107]

[0108]

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[0110]

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[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119]

[0120]

[0121]

[0122]

[0123] .

[0124] A second aspect of the present invention relates to an organic electroluminescent device comprising a cathode, an anode, and a light-emitting layer located between the cathode and the anode, the light-emitting layer comprising a triazine-containing organic compound as described above.

[0125] Furthermore, the light-emitting layer comprises a first host material H1 and a second host material H2, wherein the first host material H1 is selected from triazine-containing organic compounds as described above.

[0126] Furthermore, the second host material H2 is selected from hole transport type host materials; preferably, the second host material H2 is selected from carbazole derivatives, indolecarbazole derivatives, bicarbazole derivatives, or aromatic amine derivatives.

[0127] In one specific embodiment, the second main material H2 is selected from any of the following structures, but is not limited thereto:

[0128]

[0129]

[0130]

[0131]

[0132]

[0133]

[0134] .

[0135] Furthermore, the light-emitting layer further comprises a light-emitting guest material, which is selected from metal complexes; preferably, the light-emitting guest material is selected from Ir-based metal complexes.

[0136] In one specific embodiment, the organic electroluminescent device according to the present invention comprises, from bottom to top, an anode layer, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode layer; the light-emitting layer comprises a triazine-containing organic compound as described above.

[0137] In some embodiments, the organic electroluminescent device further includes a substrate. The substrate may be located on the side of the anode away from the light-emitting layer, or on the side of the cathode away from the light-emitting layer. The substrate may be opaque or transparent. The substrate may also be rigid or flexible; for example, the substrate material may be plastic, metal, semiconductor wafer, or glass. Preferably, the substrate has a smooth surface, and a substrate without surface defects is particularly desirable. In a preferred embodiment, the substrate is glass, polyethylene terephthalate (PET), or polyethylene glycol (2,6-naphthalene) (PEN).

[0138] The anode material can be any anode material known in the art for use in organic electronic devices, such as conductive metals, conductive metal oxides, or conductive polymers. As an example, the anode material can be selected from, but is not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, and aluminum-doped zinc oxide (AZO). Other suitable anode materials are known and can be readily selected by those skilled in the art.

[0139] The cathode material can be any cathode material known in the art for use in organic electronic devices, such as a conductive metal or conductive metal oxide. As an example, the cathode material can be selected from, but is not limited to, at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, and ITO. The cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition method, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.

[0140] The hole injection layer reduces the surface roughness of ITO, decreases internal defects in the device, and lowers the hole injection barrier. The material of the hole injection layer can be any material known in the art for hole injection layers, such as, but not limited to, HAT-CN, F4-TCQN, 1-TNATA, 2-TNATA, m-MTDATA, PEDOT:PSS, MoO3, AgO, etc.

[0141] The hole transport layer improves the hole transport efficiency in the device and blocks electrons within the light-emitting layer. The material of the hole transport layer can be any material known in the art for hole transport layers, for example, it can be selected from aromatic amine organic compounds, including but not limited to NPB, CBP, TFB, TCTA, TAPC, TPD, Spiro-TAD, TDATA, etc.

[0142] The electron transport layer facilitates electron transport. The electron transport material is one that advantageously receives electrons from the cathode and transports them to the light-emitting layer; materials with high electron mobility are suitable. The electron transport layer may include heterocyclic compounds, such as pyridine derivatives, pyrimidine derivatives, triazine derivatives, benzimidazole derivatives, etc.

[0143] The electron injection layer serves to lower the electron injection barrier between the cathode and the organic layer, enabling electrons to be effectively injected into the organic layer. The electron injection layer material includes, but is not limited to, the materials listed below, such as metals, metal compounds, and metal oxides. Specific examples may include lithium (Li), lithium fluoride (LiF), lithium 8-hydroxyquinoline (LiQ), cesium fluoride (CsF), lithium oxide (Li₂O), cesium carbonate (Cs₂CO₃), etc., but are not limited to these.

[0144] This invention also relates to electronic devices incorporating the aforementioned organic electroluminescent devices. This invention relates to the application of organic electroluminescent devices in various electronic devices. These electronic devices may be, but are not limited to, display devices, lighting devices, light sources, and sensors.

[0145] The present invention will be specifically illustrated below through specific examples of compound preparation and device effect experiments. The following examples are only some examples of the present invention and are not intended to limit the present invention.

[0146] Examples of synthesis of triazine-containing organic compounds

[0147] This invention does not impose any particular restrictions on the source of the raw materials used in the following reactions; commercially available raw materials or preparation methods well known to those skilled in the art can be used. This invention also does not impose any particular restrictions on the following reactions; conventional reactions well known to those skilled in the art can be used.

[0148] Synthesis Example 1: Synthesis of Compound Example (1)

[0149]

[0150] Synthesis of compound 1-1:

[0151] Accurately weigh compound A (57.2 g, 0.2 mol), 2-pyridineboronic acid (27.1 g, 0.22 mol), anhydrous potassium carbonate (55.2 g, 0.4 mol), tetrakis(triphenylphosphine)palladium (2.31 g, 2 mmol), toluene (850 mL), and water (170 mL), and add them sequentially to a dry 2000 mL three-necked flask. After purging with nitrogen three times, the mixture was heated to 90 °C and reacted for 5 hours. After the reactants had completely reacted, the mixture was cooled to room temperature. After dilution with water, the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and then distilled under reduced pressure to remove excess solvent. The mixture was then subjected to silica gel column chromatography with PE:EA = 5:1 (volume ratio) as the eluent. Approximately 34.16 g of compound 1-1 was obtained, with a yield of 60.1%.

[0152] Synthesis of compounds 1-2:

[0153] Accurately weigh 28.4 g (0.1 mol) of compound 1-1, 33.6 g (0.1 mol) of 1,8-dibromophenanthrene, 19.2 g (0.2 mol) of sodium tert-butoxide, 0.56 g (1 mmol) of dibenzylacetone palladium, 1.15 g (2 mmol) of 4,5-bis(diphenylphosphine-9,9-dimethyloxanthracene), and 500 mL of toluene, and add them sequentially to a dry 1000 mL three-necked flask. Purge with nitrogen three times, and heat to 110 °C for 8 hours. After the reactants have completely reacted, cool to room temperature, dilute with water, and extract three times with ethyl acetate. Combine the organic phases, dry with anhydrous magnesium sulfate, remove excess solvent by vacuum distillation, and perform silica gel column chromatography with a PE:EA ratio of 8:1 (v / v). Approximately 36.87 g of compound 1-2 was obtained, with a yield of 68.3%.

[0154] Synthesis of compounds 1-3:

[0155] Accurately weigh compounds 1-2 (10.8 g, 20 mmol), pinacol diboronate (10.14 g, 40 mmol), bis(dibenzylacetone)palladium (0.11 g, 0.2 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.18 g, 0.4 mmol), anhydrous potassium acetate (3.92 g, 40 mmol), and dioxane (250 mL); add them sequentially to a 500 mL dry three-necked flask. Purge with nitrogen three times, heat to 90 °C, and react for 2 hours until the reactants are completely reacted. After cooling to room temperature, dilute with water and extract three times with ethyl acetate. Combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 3:1 (v / v). Approximately 8.52 g of compounds 1-3 were obtained, with a yield of 72.6%.

[0156] Synthesis of compound (1):

[0157] Accurately weigh compounds 1-3 (5.87 g, 10 mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine (3.88 g, 10 mmol), tetra-triphenylphosphine palladium (0.11 g, 0.1 mmol), anhydrous potassium carbonate (3.31 g, 24 mmol), 100 mL of dioxane, and 20 mL of water; add them sequentially to a 500 mL dry three-necked flask. After purging with nitrogen three times, the mixture was heated to 90 °C and reacted for 3 hours. After the starting material had completely reacted, the mixture was cooled to room temperature, diluted with water, and extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 8:1 (volume ratio) as the eluent. Approximately 6.36 g of compound (1) was obtained, with a yield of 82.9% and MS: 767.34.

[0158] Synthesis Example 2: Synthesis of Compound (17)

[0159]

[0160] Synthesis of compound 17-1:

[0161] Accurately weigh compound B (15.1 g, 50 mmol), pinacol diboronate (25.39 g, 0.1 mol), bis(dibenzylacetone)palladium (0.28 g, 0.5 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (0.48 g, 1 mmol), anhydrous potassium acetate (9.8 g, 0.1 mol), and 500 mL of dioxane, and add them sequentially to a dry 1000 mL three-necked flask. Purge with nitrogen three times, heat to 90 °C, and react for 2 hours until the reactants are completely reacted. After cooling to room temperature, dilute with water, and extract three times with ethyl acetate. Combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 3:1 (v / v). Approximately 14.28 g of compound 17-1 was obtained, with a yield of 81.7%.

[0162] Synthesis of compound 17-2:

[0163] Accurately weigh 14.0 g (40 mmol) of compound 17-1, 7.78 g (48 mmol) of 2-bromopyridine-D4, 11.04 g (80 mmol) of anhydrous potassium carbonate, 0.46 g (0.4 mmol) of tetraphenylphosphine-palladium, 150 mL of toluene, and 30 mL of water, and add them sequentially to a 500 mL three-necked flask. After purging with nitrogen three times, the mixture was heated to 90 °C and reacted for 6 hours. After the starting material had completely reacted, the mixture was cooled to room temperature, diluted with water, and extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 1:1 (v / v). Approximately 11.24 g of compound 17-2 was obtained, with a yield of 92.2%.

[0164] Synthesis of compound 17-3:

[0165] Accurately weigh compound 17-2 (9.14 g, 30 mmol), 1,8-dibromophenanthrene (10.08 g, 30 mmol), sodium tert-butoxide (5.76 g, 60 mmol), bis(benzylacetone)palladium (0.17 g, 0.3 mmol), 4,5-bis(diphenylphosphine-9,9-dimethyloxanthracene) (0.34 g, 0.6 mmol), and 300 mL of toluene into a 1000 mL three-necked flask. Purge with nitrogen three times, heat to 110 °C, and react for 8 hours. After complete reaction, cool to room temperature, dilute with water, and extract three times with ethyl acetate. Combine the organic phases, dry with anhydrous magnesium sulfate, remove excess solvent by vacuum distillation, and perform silica gel column chromatography with a PE:EA ratio of 5:1 (v / v). Approximately 12.32 g of compound 17-3 was obtained, with a yield of 73.4%.

[0166] Synthesis of compound 17-4:

[0167] Accurately weigh 10.76 g (20 mmol) of compound 17-3, 10.14 g (40 mmol) of pinacol diboronate, 0.11 g (0.2 mmol) of bis(dibenzylacetone)palladium, 0.18 g (0.4 mmol) of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl, 3.92 g (40 mmol) of anhydrous potassium acetate, and 250 mL of dioxane, and add them sequentially to a 500 mL three-necked flask. Purge with nitrogen three times, heat to 90 °C, and react for 2 hours. After the reactants have completely reacted, cool to room temperature, dilute with water, and extract three times with ethyl acetate. Combine the organic phases, dry to anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 3:1 (v / v). Approximately 9.24 g of compound 17-4 was obtained, with a yield of 76.1%.

[0168] Synthesis of compound 17-5:

[0169] Accurately weigh 5.7 g (15 mmol) of 2,4-bis(4-tert-butyl)phenyl-6-chloro-1,3,5-triazine, 3-bromophenylboronic acid (3.02 g, 15 mmol), tetrakis(triphenylphosphine)palladium (0.17 g, 0.15 mmol), anhydrous potassium carbonate (4.14 g, 30 mmol), 150 mL of dioxane, and 30 mL of water, and add them sequentially to a 500 mL three-necked flask. After purging with nitrogen three times, the mixture was heated to 90 °C and reacted for 6 hours. After the starting material had completely reacted, the mixture was cooled to room temperature, diluted with water, and extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 8:1 (v / v). Approximately 4.40 g of compound 17-5 was obtained, with a yield of 58.7%.

[0170] Synthesis of compound (17):

[0171] Accurately weigh compound 17-4 (4.25 g, 7 mmol), compound 17-5 (3.5 g, 7 mmol), tetrakis(triphenylphosphine)palladium (0.08 g, 0.07 mmol), anhydrous potassium carbonate (1.93 g, 14 mmol), 50 mL of dioxane, and 10 mL of water, and add them sequentially to a 100 mL three-necked flask. After purging with nitrogen three times, the mixture was heated to 90 °C and reacted for 3 hours. After the reactants had completely reacted, the mixture was cooled to room temperature, diluted with water, and extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 2:1 (volume ratio) as the eluent. Approximately 4.31 g of compound (17) was obtained, with a yield of 68.4% and MS: 900.42.

[0172] Synthesis Example 3: Synthesis of Compound (19)

[0173]

[0174] Synthesis of compound 19-1:

[0175] Accurately weigh 92 g (0.5 mol) of compound 2,4,6-trichloro-1,3,5-triazine, 128 g (0.5 mol) of 4-(1-adamantyl)phenylboronic acid, 5.77 g (5 mmol) of tetrakis(triphenylphosphine)palladium, 138 g (1 mol) of anhydrous potassium carbonate, 1000 mL of dioxane, and 200 mL of water, and add them sequentially to a 2000 mL three-necked flask. After purging with nitrogen three times, the mixture was heated to 90 °C and reacted for 6 hours. After the starting material had completely reacted, the mixture was cooled to room temperature, diluted with water, and extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 8:1 (v / v). Approximately 118.18 g of compound 19-1 was obtained, with a yield of 65.7%.

[0176] Synthesis of compound 19-2:

[0177] Accurately weigh 108 g (0.3 mol) of compound 19-1, 53.4 g (0.3 mol) of 4-tert-butylphenylboronic acid, 3.47 g (3 mmol) of tetrakis(triphenylphosphine)-palladium, 82.8 g (0.6 mol) of anhydrous potassium carbonate, 1000 mL of dioxane, and 200 mL of water, and add them sequentially to a 2000 mL three-necked flask. After purging with nitrogen three times, the mixture was heated to 90 °C and reacted for 8 hours. After the reactants had completely reacted, the mixture was cooled to room temperature, diluted with water, and extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 10:1 (v / v). Approximately 86.47 g of compound 19-2 was obtained, with a yield of 62.9%.

[0178] Synthesis of compound 19-3:

[0179] Accurately weigh 68.7 g (0.15 mol) of compound 19-2, 3-bromophenylboronic acid (30.2 g (0.15 mol)), tetrakis(triphenylphosphine)palladium (1.73 g (1.5 mmol)), anhydrous potassium carbonate (41.4 g (0.3 mol)), 800 mL of dioxane, and 160 mL of water, and add them sequentially to a 2000 mL three-necked flask. After purging with nitrogen three times, the mixture was heated to 90 °C and reacted for 6 hours. After the starting materials had completely reacted, the mixture was cooled to room temperature, diluted with water, and extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 10:1 (volume ratio) as the eluent. Approximately 62.25 g of compound 19-3 was obtained, with a yield of 71.7%.

[0180] Synthesis of compound (19):

[0181] Accurately weigh compound 19-3 (4.76 g, 8.23 ​​mmol), compound 17-4 (5.0 g, 8.23 ​​mmol), tetraphenylphosphine palladium (95 mg, 0.08 mmol), anhydrous potassium carbonate (2.26 g, 16.4 mmol), 50 mL of dioxane, and 10 mL of water, and add them sequentially to a 100 mL three-necked flask. After purging with nitrogen three times, the mixture was heated to 90 °C and reacted for 2 hours. After the reactants had completely reacted, the mixture was cooled to room temperature, diluted with water, and extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 10:1 (volume ratio) as the eluent. Approximately 6.74 g of compound (19) was obtained, with a yield of 83.7% and MS: 978.19.

[0182] Synthesis Example 4: Synthesis of Compound (26)

[0183]

[0184] Synthesis of compound 26-1:

[0185] Accurately weigh compound B (15.1 g, 50 mol), 2-pyridineboronic acid (12.2 g, 0.1 mol), anhydrous potassium carbonate (13.8 g, 0.1 mol), tetrakis(triphenylphosphine)palladium (0.58 g, 0.5 mmol), 500 mL toluene, and 100 mL water, and add them sequentially to a dry 1000 mL three-necked flask. After purging with nitrogen three times, the mixture was heated to 90 °C and reacted for 5 hours. After the reactants had completely reacted, the mixture was cooled to room temperature. After dilution with water, the mixture was extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and then distilled under reduced pressure to remove excess solvent. The mixture was then subjected to silica gel column chromatography with PE:EA = 5:1 (volume ratio) as the eluent. Approximately 12.53 g of compound 26-1 was obtained, with a yield of 83.4%.

[0186] Synthesis of compound 26-2:

[0187] Accurately weigh 12.0 g (40 mmol) of compound 26-1, 1,8-dibromophenanthrene (13.44 g (40 mmol), sodium tert-butoxide (7.68 g (80 mmol), bis(benzylacetone)palladium (0.22 g (0.4 mmol), 4,5-bis(diphenylphosphine-9,9-dimethyloxanthracene) (0.45 g (0.8 mmol), and 300 mL of toluene, and add them sequentially to a 500 mL three-necked flask. Purge with nitrogen three times; heat to 110 °C and react for 8 hours. After the starting material has completely reacted, cool to room temperature, dilute with water, and extract three times with ethyl acetate. Combine the organic phases, dry with anhydrous magnesium sulfate, remove excess solvent by vacuum distillation, and perform silica gel column chromatography with a PE:EA ratio of 5:1 (v / v). This yields approximately 17.15 g of compound 26-2, with a yield of 77.2%.

[0188] Synthesis of compound 26-3:

[0189] Accurately weigh 11.11 g (20 mmol) of compound 26-2, 10.14 g (40 mmol) of pinacol diboronate, 0.11 g (0.2 mmol) of bis(dibenzylacetone)palladium, 0.18 g (0.4 mmol) of 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl, 3.92 g (40 mmol) of anhydrous potassium acetate, and 250 mL of dioxane, and add them sequentially to a 500 mL three-necked flask. Purge with nitrogen three times, heat to 90 °C, and react for 2 hours until the reactants are completely reacted. After cooling to room temperature, dilute with water, extract three times with ethyl acetate, combine the organic phases, dry to anhydrous sodium sulfate, remove excess solvent by vacuum distillation, and perform silica gel column chromatography with PE:EA = 2:1 (v / v). Approximately 11.12 g of compound 26-3 was obtained, with a yield of 92.3%.

[0190] Synthesis of compound (26):

[0191] Accurately weigh compound 26-3 (9.04 g, 15 mmol), compound 26-4 (6.97 g, 15 mmol), tetraphenylphosphine palladium (0.17 g, 0.15 mmol), anhydrous potassium carbonate (4.14 g, 30 mmol), 100 mL of dioxane, and 20 mL of water, and add them sequentially to a 250 mL three-necked flask. After purging with nitrogen three times, the mixture was heated to 90 °C and reacted for 2 hours. After the reactants had completely reacted, the mixture was cooled to room temperature, diluted with water, and extracted three times with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the excess solvent was removed by vacuum distillation. The mixture was then subjected to silica gel column chromatography with PE:EA = 8:1 (volume ratio) as the eluent. Approximately 10.84 g of compound (26) was obtained, with a yield of 84.0% and MS: 859.83.

[0192] Synthesis Example 5: Synthesis of Compound (28)

[0193]

[0194] Synthesis of compound 28-1:

[0195] The synthesis of compound 28-1 is similar to that of compound 1-1, except that compound 2-pyridineboronic acid is replaced with 3-pyridineboronic acid of equimolar molecular weight, resulting in approximately 36.23 g of compound 28-1, with a yield of 63.7%.

[0196] Synthesis of compound 28-2:

[0197] The synthesis of compounds 1-2 is similar to that of compounds 28-1, but with the difference that compounds 1-1 were replaced with compounds 28-1 of equal molecular weight, resulting in approximately 36.07 g of compound 28-2, with a yield of 66.8%.

[0198] Synthesis of compound 28-3:

[0199] The synthesis of compounds 1-3 is similar to that of compounds 1-2, but with the difference that compounds 1-2 were replaced with compounds 28-2 of equimolar molecular weight, yielding approximately 8.69 g of compound 28-3, with a yield of 74.0%.

[0200] Synthesis of compound 28-5:

[0201] The synthesis of compound 17-5 was referenced, with the difference being that 2,4-bis(4-tert-butyl)phenyl-6-chloro-1,3,5-triazine was replaced with compound 28-4 of equimolar molecular weight, yielding approximately 4.03 g of compound 28-5, with a yield of 61.3%.

[0202] Synthesis of compound (28):

[0203] The synthesis of the reference compound (17) differed in that: compound 17-4 was replaced with compound 28-3 of equimolar molecular weight, and compound 17-5 was replaced with compound 28-5 of equimolar molecular weight, to obtain approximately 4.54 g of compound (28), with a yield of 79.3% and MS: 817.69.

[0204] Synthesis Example 6: Synthesis of Compound (68)

[0205]

[0206] Synthesis of compound 68-1:

[0207] The synthesis of compound 1-1 is similar to that of compound 68-1, except that 2-pyridineboronic acid is replaced with 4-pyridineboronic acid of equal molecular weight, resulting in approximately 38.25 g of compound 68-1 with a yield of 67.3%.

[0208] Synthesis of compound 68-2:

[0209] Referring to the synthesis of compounds 1-2, replacing compound 1-1 with compound 68-1 of equimolar molecular weight yielded approximately 33.88 g of compound 68-2, with a yield of 62.8%.

[0210] Synthesis of compound 68-3:

[0211] Referring to the synthesis of compounds 1-3, replacing compound 1-2 with compound 68-2 of equimolar molecular weight yielded approximately 9.04 g of compound 68-3, with a yield of 77.1%.

[0212] Synthesis of Compound 68-4

[0213] The synthesis of compound 17-5 was referenced, with the difference being that 2,4-bis(4-tert-butyl)phenyl-6-chloro-1,3,5-triazine was replaced with equimolar amounts of 2-chloro-4,6-di(phenyl-D5)-1,3,5-triazine, yielding approximately 4.34 g of compound 68-4, with a yield of 72.6%.

[0214] Synthesis of compound (68):

[0215] The synthesis of the reference compound (17) differs in that: compound 17-4 is replaced with compound 68-3 of equimolar molecular weight, and compound 17-5 is replaced with compound 68-4 of equimolar molecular weight, to obtain approximately 4.15 g of compound (28), with a yield of 76.2% and MS: 778.23.

[0216] Synthesis Example 7: Synthesis of Compound (78)

[0217]

[0218] Synthesis of compound 78-1:

[0219] The synthesis of compound 17-1 was referenced, with the difference being that compound B was replaced with compound C of equimolar molecular weight, yielding approximately 14.53 g of compound 78-1, with a yield of 87.2%.

[0220] Synthesis of compound 78-2:

[0221] The synthesis of compound 17-2 was referenced, with the difference being that compound 17-1 was replaced with compound 78-1 of equimolar molecular weight, yielding approximately 9.43 g of compound 78-2, with a yield of 81.8%.

[0222] Synthesis of compound 78-3:

[0223] The synthesis of compound 17-3 was referenced, with the difference being that compound 17-2 was replaced with compound 78-2 of equimolar molecular weight, yielding approximately 12.44 g of compound 78-3, with a yield of 76.3%.

[0224] Synthesis of compound 78-4:

[0225] The synthesis of compound 17-4 was referenced, with the difference being that compound 17-3 was replaced with compound 78-3 of equimolar molecular weight, yielding approximately 9.43 g of compound 78-4, with a yield of 79.8%.

[0226] Synthesis of compound (78):

[0227] The synthesis of compound (17) was referenced, with the difference that compound 17-4 was replaced with compound 78-4 of equimolar molecular weight, and compound 17-5 was replaced with 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine of equimolar molecular weight, to obtain approximately 3.51 g of compound (78), with a yield of 65.0% and MS: 771.46.

[0228] Synthesis Example 8: Synthesis of Compound (119)

[0229]

[0230] Synthesis of compound 119-1:

[0231] The synthesis of compound 1-1 was referenced, with the difference that compound A was replaced with an equimolar amount of compound D, and 2-pyridineboronic acid was replaced with an equimolar amount of 3-pyridineboronic acid, yielding approximately 38.51 g of compound 119-1. The yield was 64.1%.

[0232] Synthesis of compound 119-2:

[0233] The synthesis of compounds 1-2 was referenced, with the difference being that compound 1-1 was replaced with compound 119-1 of equimolar molecular weight, yielding approximately 40.99 g of compound 119-2. The yield was 73.8%.

[0234] Synthesis of compound 119-3:

[0235] The synthesis of compounds 1-3 is similar to that of compounds 1-2, but with the difference that compounds 1-2 were replaced with compounds 119-2 of equimolar molecular weight, resulting in approximately 10.15 g of compound 119-3, with a yield of 84.2%.

[0236] Synthesis of compound (119):

[0237] The synthesis of compound (1) was referenced, with the following differences: compounds 1-3 were replaced with compounds 119-3 of equimolar molecular weight, and compounds 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine were replaced with compounds 119-4 of equimolar molecular weight, resulting in approximately 6.23 g of compound (119) with a yield of 74.1% and MS: 840.29.

[0238] Synthesis Example 9: Synthesis of Compound (144)

[0239]

[0240] Synthesis of compound 144-1:

[0241] The synthesis of compound 17-1 was referenced, with the difference being that compound B was replaced with compound D of equimolar molecular weight, yielding approximately 14.30 g of compound 144-1, with a yield of 81.9%.

[0242] Synthesis of compound 144-2:

[0243] The synthesis of compound 17-2 is similar to that of compound 17-1, but with the difference that compound 17-1 was replaced with compound 144-1 of equimolar molecular weight, yielding approximately 10.96 g of compound 144-2, with a yield of 90.0%.

[0244] Synthesis of compound 144-3:

[0245] The synthesis of compound 17-3 is similar to that of compound 17-2, but with the difference that compound 17-2 was replaced with compound 144-2 of equimolar molecular weight, yielding approximately 13.25 g of compound 144-3, with a yield of 78.9%.

[0246] Synthesis of compound 144-4:

[0247] The synthesis of compound 17-4 was referenced, with the difference being that compound 17-3 was replaced with compound 144-3, yielding approximately 10.73 g of compound 144-4. The yield was 88.4%.

[0248] Synthesis of compound (144):

[0249] The synthesis of compound (17) was referenced, with the following differences: compound 17-4 was replaced with an equimolar amount of compound 144-4, and compound 17-5 was replaced with an equimolar amount of 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine, yielding approximately 3.81 g of compound (144), with a yield of 69.1% and an MS value of 787.27. The mass spectrum is shown below. Figure 1 As shown.

[0250] Synthesis Example 10: Synthesis of Compound (172)

[0251]

[0252] Synthesis of compound 172-1:

[0253] The synthesis of compound 1-1 is referenced, with the difference that compound A is replaced with compound E of equimolar molecular weight, and compound 2-pyridineboronic acid is replaced with compound 4-pyridineboronic acid of equimolar molecular weight, to obtain approximately 35.48 g of compound 172-1, with a yield of 62.4%.

[0254] Synthesis of compound 172-2:

[0255] The synthesis of compounds 1-2 is similar to that of compounds 1-1, but with the difference that compounds 1-1 are replaced with compounds 172-1 of equimolar molecular weight, resulting in approximately 42.34 g of compound 172-2, with a yield of 78.5%.

[0256] Synthesis of compound 172-3:

[0257] The synthesis of compounds 1-3 is similar to that of compounds 1-2, but with the difference that compounds 1-2 were replaced with compounds 172-2 of equimolar molecular weight, yielding approximately 9.01 g of compound 172-3, with a yield of 76.8%.

[0258] Synthesis of compound 172-5:

[0259] The synthesis of compound 17-5 was referenced, with the difference being that 2,4-bis(4-tert-butyl)phenyl-6-chloro-1,3,5-triazine was replaced with compound 172-4 of equimolar molecular weight, yielding approximately 4.29 g of compound 172-5 in a yield of 55.6%.

[0260] Synthesis of compound (172):

[0261] The synthesis of the reference compound (17) differs in that: compound 17-4 is replaced with compound 172-3 of equimolar molecular weight, and compound 17-5 is replaced with compound 172-5 of equimolar molecular weight, to obtain approximately 4.68 g of compound (172), with a yield of 74.8% and MS value of 893.75.

[0262] Synthesis Example 11: Synthesis of Compound (178)

[0263]

[0264] Synthesis of compound 178-1:

[0265] The synthesis of compound 1-1 is similar to that of compound A, but with the difference that compound A was replaced with compound F of equal molecular weight, resulting in approximately 48.60 g of compound 178-1, with a yield of 80.9%.

[0266] Synthesis of compound 178-2:

[0267] The synthesis of compounds 1-2 is similar to that of compounds 1-1, but with the difference that compounds 1-1 are replaced with compounds 178-1 of equal molecular weight, resulting in approximately 40.34 g of compound 178-2, with a yield of 72.6%.

[0268] Synthesis of compound 178-3:

[0269] The synthesis of compounds 1-3 is similar to that of compounds 1-2, but with the difference that compounds 1-2 were replaced with compounds 178-2 of equimolar molecular weight, resulting in approximately 10.42 g of compound 178-3, with a yield of 86.5%.

[0270] Synthesis of compound (178):

[0271] The synthesis of the reference compound (1) differs in that: compounds 1-3 are replaced with compounds 178-3 of equimolar molecular weight, resulting in approximately 5.13 g of compound (178), yield 65.4%, MS: 784.06.

[0272] Synthesis Example 12: Synthesis of Compound (200)

[0273]

[0274] Synthesis of compound 200-1:

[0275] The synthesis of compound 1-1 is referenced, with the difference that compound A is replaced with compound G of equimolar molecular weight, and 2-pyridineboronic acid is replaced with 4-pyridineboronic acid of equimolar molecular weight, to obtain approximately 39.56 g of compound 200-1, with a yield of 69.9%.

[0276] Synthesis of compound 200-2:

[0277] The synthesis of compounds 1-2 is similar to that of compounds 200-1, but with the difference that compounds 1-1 were replaced with compounds 200-1 of equal molecular weight, resulting in approximately 44.83 g of compound 200-2, with a yield of 83.1%.

[0278] Synthesis of compound 200-3:

[0279] The synthesis of compounds 1-3 is similar to that of compounds 1-2, but with the difference that compounds 1-2 were replaced with compounds 200-2 of equimolar molecular weight, resulting in approximately 9.10 g of compound 200-3, with a yield of 77.6%.

[0280] Synthesis of compound 200-5:

[0281] The synthesis of compound 17-5 was referenced, with the difference being that 2,4-bis(4-tert-butyl)phenyl-6-chloro-1,3,5-triazine was replaced with compound 200-4 of equimolar molecular weight, yielding approximately 5.39 g of compound 200-5, with a yield of 69.1%.

[0282] Synthesis of compound (200):

[0283] The synthesis of the reference compound (17) differs in that: compound 17-4 is replaced with compound 200-3 of equimolar molecular weight, and compound 17-5 is replaced with compound 200-5 of equimolar molecular weight, to obtain approximately 5.13 g of compound (200), with a yield of 81.4% and MS: 900.22.

[0284] Synthesis Example 13: Synthesis of Compound (206)

[0285]

[0286] Synthesis of compound 206-1:

[0287] The synthesis of compound 1-1 is referenced, except that compound A is replaced with compound H of equimolar molecular weight, resulting in approximately 40.71 g of compound 206-1, with a yield of 71.6%.

[0288] Synthesis of compound 206-2:

[0289] The synthesis of compounds 1-2 is similar to that of compounds 1-1, but with the difference that compounds 1-1 are replaced with compounds 206-1 of equal molecular weight, resulting in approximately 44.83 g of compound 206-2, with a yield of 83.1%.

[0290] Synthesis of compound 206-3:

[0291] The synthesis of compounds 1-3 was referenced, with the difference being that compounds 1-2 were replaced with compounds 206-2 of equal molecular weight, yielding approximately 7.65 g of compound 206-3. The yield was 65.2%.

[0292] Synthesis of compound 206-5:

[0293] The synthesis of compound 17-5 was referenced, with the difference that 2,4-bis(4-tert-butyl)phenyl-6-chloro-1,3,5-triazine was replaced with compound 206-4 of equimolar molecular weight, yielding approximately 5.38 g of compound 206-5. The yield was 76.3%.

[0294] Synthesis of compound (206):

[0295] The synthesis of compound (1) was referenced, with the difference that compounds 1-3 were replaced with compounds 206-3 of equimolar molecular weight, and compounds 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine were replaced with compounds 206-5 of equimolar molecular weight, yielding approximately 7.01 g of compound (206). Yield: 82.4%, MS: 850.46.

[0296] Synthesis Example 14: Synthesis of Compound (226)

[0297]

[0298] Synthesis of compound 226-1:

[0299] Prepare a 2000 mL dry three-necked flask. Accurately weigh compound I (105.6 g, 0.5 mol) and dissolve it in 1 L of anhydrous tetrahydrofuran. After purging with nitrogen three times, cool to -78 °C. Slowly add 240 mL of 2.5 mol / L n-butyllithium to the reactor. After reacting at this temperature for 3 hours, slowly add liquid bromine (80 g, 0.5 mol) dropwise to the reactor. After reacting at this temperature for 30 minutes, raise the temperature to room temperature. Once the reactants have reacted completely, quench with a saturated sodium sulfite aqueous solution. After diluting with water, extract three times with ethyl acetate. Combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 5:1 (volume ratio) as the eluent. Approximately 104.93 g of compound 226-1 is obtained, with a yield of 72.3%.

[0300] Synthesis of compound 226-2:

[0301] Prepare a 2000 mL dry three-necked flask. Accurately weigh compound 226-2 (87.1 g, 0.3 mol), pinacol diboronate (152.36 g, 0.6 mol), bis(dibenzylacetone)palladium (1.66 g, 3 mmol), 2-dicyclohexylphosphine-2',4',6'-triisopropylbiphenyl (2.85 g, 6 mmol), anhydrous potassium acetate (57.6 g, 0.6 mol), and 1000 mL of dioxane, and add them sequentially to the three-necked flask. Purge with nitrogen three times, heat to 90 °C and react for 6 hours until the starting material has completely reacted. After cooling to room temperature, dilute with water and extract three times with ethyl acetate. Combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 2:1 (volume ratio) as the eluent. Approximately 68.17 g of compound 226-2 was obtained, with a yield of 67.4%.

[0302] Synthesis of compound 226-4:

[0303] Prepare a 1000 mL dry three-necked flask. Accurately weigh compound 226-2 (50.6 g, 0.15 mol), compound 226-3 (35.2 g, 0.15 mol), tetrakis(triphenylphosphine)palladium (1.73 g, 1.5 mmol), anhydrous potassium carbonate (41.4 g, 0.3 mol), 500 mL of dioxane, and 100 mL of water, and add them sequentially to the three-necked flask. After purging with nitrogen three times, heat to 90 °C and react for 6 hours. After the starting materials have completely reacted, cool to room temperature, dilute with water, and extract three times with ethyl acetate. Combine the organic phases, dry with anhydrous sodium sulfate, and remove excess solvent by vacuum distillation. Perform silica gel column chromatography with PE:EA = 5:1 (v / v). Approximately 32.31 g of compound 226-4 was obtained. The yield was 52.6%.

[0304] Synthesis of compound 226-5:

[0305] Prepare a 1000 mL dry three-necked flask. Accurately weigh compound 226-4 (28.7 g, 70 mmol), triethyl phosphite (58.1 g, 0.35 mol), and 500 mL of isopropylbenzene, and add them sequentially to the flask. After purging with nitrogen three times, heat to 160 °C and react for 24 hours. After the reactants have reacted completely, cool to room temperature, remove excess solvent by vacuum distillation, and perform silica gel column chromatography with PE:EA = 8:1 (volume ratio) as the eluent. Approximately 20.19 g of compound 226-5 was obtained, with a yield of 76.4%.

[0306] Synthesis of compound 226-6:

[0307] The synthesis of compound 26-2 is similar to that of compound 26-1, but with the difference that compound 26-1 is replaced with compound 226-5 of equimolar molecular weight, resulting in approximately 26.98 g of compound 226-6, with a yield of 85.3%.

[0308] Synthesis of compound 226-7:

[0309] The synthesis of compound 26-3 was referenced, with the difference being that compound 26-2 was replaced with an equimolar amount of compound 226-6, yielding approximately 10.57 g of compound 226-7. The yield was 77.8%.

[0310] Synthesis of compound (226):

[0311] The synthesis of the reference compound (1) differs in that compounds 1-3 are replaced with compounds 226-7 of equimolar molecular weight, resulting in approximately 6.36 g of compound (226) with a yield of 73.9% and MS: 860.79.

[0312] Synthesis Example 15: Synthesis of Compound (239)

[0313]

[0314] Synthesis of compound 239-1:

[0315] The synthesis of compound 226-1 was referenced, with the difference being that compound I was replaced with compound J of equimolar molecular weight, yielding approximately 101.70 g of compound 239-1, with a yield of 74.2%.

[0316] Synthesis of compound 239-2:

[0317] The synthesis of compound 226-2 is similar to that of compound 226-1, but with the difference that compound 226-1 was replaced with compound 239-1 of equimolar molecular weight, yielding approximately 72.46 g of compound 239-2, with a yield of 75.2%.

[0318] Synthesis of compound 239-4:

[0319] The synthesis of compound 226-4 was referenced, with the difference that compound 226-2 was replaced with compound 239-2 of equimolar molecular weight, and compound 226-3 was replaced with compound 239-3 of equimolar molecular weight, yielding approximately 35.35 g of compound 239-4, with a yield of 59.9%.

[0320] Synthesis of compound 239-5:

[0321] The synthesis of compound 226-5 is similar to that of compound 226-4, but with the difference that compound 226-4 was replaced with compound 239-4 of equimolar molecular weight, yielding approximately 16.27 g of compound 239-5, with a yield of 64.3%.

[0322] Synthesis of compound 239-6:

[0323] The synthesis of compound 26-2 is similar to that of compound 26-1, but with the difference that compound 26-1 was replaced with compound 239-5 of equimolar molecular weight, yielding approximately 21.03 g of compound 239-6, with a yield of 85.3%.

[0324] Synthesis of compound 239-7:

[0325] The synthesis of compound 26-3 was referenced, with the difference being that compound 26-2 was replaced with an equimolar amount of compound 239-6, yielding approximately 8.19 g of compound 239-7, in 61.7% yield. 20 mmol

[0326] Synthesis of compound (239):

[0327] The synthesis of compound (1) was referenced, with the following differences: compounds 1-3 were replaced with compounds 239-7 of equimolar molecular weight, and compound 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine was replaced with compounds 239-8 of equimolar molecular weight, yielding approximately 6.29 g of compound 239, with a yield of 72.1% and an MS index of 873.41. The mass spectrum is shown below. Figure 2 As shown.

[0328] Synthesis Example 16: Synthesis of Compound (Ref-3)

[0329]

[0330] Synthesis of compound K-1:

[0331] The synthesis of compounds 1-2 is similar to that of compounds 1-1, but with the difference that compounds 1-1 were replaced with compounds K-0 of equimolar molecular weight, resulting in approximately 34.12 g of compound K-1 with a yield of 73.8%.

[0332] Synthesis of compound K-2:

[0333] The synthesis of compounds 1-3 was referenced, with the difference being that compounds 1-2 were replaced with compounds K-1 of equimolar molecular weight, yielding approximately 8.52 g of compound K-2. The yield was 83.6%.

[0334] Synthesis of compound (Ref-3):

[0335] The synthesis of the reference compound (1) differs in that compounds 1-3 are replaced with compound K-2 of equimolar molecular weight, resulting in approximately 5.19 g of compound (Ref-3) with a yield of 75.1% and MS: 690.68.

[0336] Device Examples

[0337] The OLED device structure provided by this invention is as follows: ITO / HI-1 (10nm) / HT-1 (60nm) / HT-2 (5nm) / common host material: EM-1 (40nm) / ET-1:LiQ (5:5,30nm) / LiQ (1nm) / Al (100nm).

[0338] The fabrication steps of the OLED-1 device are as follows:

[0339] Step a, Cleaning of ITO conductive glass substrate: Clean the ITO conductive glass sequentially with chloroform, ketone and isopropanol, and then perform ultraviolet ozone treatment;

[0340] Step b, Hole injection layer preparation: The cleaned conductive glass substrate is transferred to a nitrogen glove box and subjected to high vacuum (1×10⁻⁶).-6 Under millibar conditions, an organic compound HI-1 was vacuum-deposited on an ITO substrate to form a hole injection layer with a deposition thickness of 10 nm.

[0341] Step c, Preparation of the first hole transport layer: An organic compound HT-1 is vacuum-deposited onto the hole injection layer to form a hole transport layer with a deposition thickness of 60 nm.

[0342] Step d, Preparation of the second hole transport layer: The organic compound HT-2 is vacuum evaporated onto the first hole transport layer to form the second hole transport layer, with a deposition thickness of 5 nm.

[0343] Step e, Light-emitting layer preparation: Vacuum evaporation of co-host material and guest material EM-1 on the second hole transport layer to form a light-emitting layer with a evaporation thickness of 40 nm; wherein the co-host material includes a first host material and a second host material, the first host material is selected from compound (1), the second host material is selected from compound H2-4, and the mass ratio of compound (1): compound H2-4: EM-1 is 48:48:4.

[0344] Step f, Electron transport layer preparation: ET-1 and LiQ are vacuum-deposited onto the luminescent layer to form an electron transport layer. Specifically, in a vacuum chamber, the electron transport materials ETM-1 and LiQ are placed in different evaporation crucibles under a high vacuum environment (1×10⁻⁶). -6 An electron transport layer was obtained by co-depositing ETM-1 and LiQ at a mass ratio of 5:5 under millibars, with a deposition thickness of 30 nm.

[0345] Step g, Cathode layer preparation: LiQ / Al (1nm / 100nm) is vacuum-deposited on the electron transport layer as the cathode layer;

[0346] Step h, Encapsulation: The device is encapsulated in a nitrogen glove box using UV-cured resin.

[0347] The chemical structural formulas of HI-1, HT-1, HT-2, EM-1, and ET-1 are shown below:

[0348]

[0349] Fabrication of OLED-2 to OLED-15 devices:

[0350] The fabrication methods for OLED-2 to OLED-15 are the same as those for OLED-1, with the difference being the selection of the first host material in the emitting layer. Specifically, the first host material compound (1) in the emitting layer of OLED-1 is replaced with compounds (17), (19), (26), (28), (68), (78), (119), (144), (172), (200), (206), (226), and (239), respectively. See Table 1 for details.

[0351] OLED-Ref1-3 device fabrication:

[0352] The device fabrication method of OLED-Ref1-3 is the same as that of OLED-1. The difference is that the first host material in the light-emitting layer is different. Specifically, the host material compound (1) in the light-emitting layer of OLED-1 is replaced with compounds (Ref-1), (Ref-2) and (Ref-3).

[0353]

[0354] The performance of OLED-1 to OLED-15 and OLED-Ref 1-3 devices was characterized, and important parameters such as luminous efficiency were recorded, as shown in Table 1. Luminous efficiency is defined as the current density at 10 mA / cm². 2 The value obtained at that time.

[0355] Table 1

[0356]

[0357] As shown in Table 1, the triazine-containing organic compounds developed in this invention, when used as the main material in the emissive layer of OLED devices, significantly improve the luminous efficiency compared to comparative examples 1-3. This is because the present invention selects and optimizes the connecting units and connecting sites in the compound structure, resulting in a larger conjugated system and a suitable energy level structure. Specifically, through… Introducing unsubstituted or deuterated electron-withdrawing pyridyl groups into the light-emitting layer can enhance the electron transport capability of organic compounds, effectively increase their molecular weight, and improve their molecular configuration and stability. When combined with hole-transporting host materials and applied to the light-emitting layer, it can achieve efficient charge transport and effectively improve the luminous efficiency of the device.

[0358] Furthermore, the luminous efficiency of OLED-1 to OLED-6 devices exceeded 85 cd / A, indicating that when unsubstituted or deuterated pyridine groups are present... When the 1-position is replaced, it is more conducive to charge transport when used as the main material in the OLED light-emitting layer.

[0359] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0360] The embodiments described above are merely illustrative of several implementation methods of this application, and while the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the patent application. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of this application, and these all fall within the protection scope of this application. Therefore, the protection scope of this patent application should be determined by the appended claims.

Claims

1. An organic compound containing triazine, characterized in that: It has a structure as shown in general formula (I): （I） in: R1 is selected from pyridinyl groups that are unsubstituted or substituted with one or more deuterium (-D); m1 is selected from 0 or 1; m2 is selected from 0 or 1; m1 + m2 is greater than or equal to 1; Y is selected from O or S; L1 and L2 are independently selected from single bonds, unsubstituted bonds, or bonds containing one or more substituents R. 0 Substituted aromatic groups having 6-20 carbon atoms; or unsubstituted or with one or more substituents R. 0 Substituted heteroaromatic groups having 5-20 ring atoms; Ar1 and Ar2 are independently selected from unsubstituted or substituted groups R. 0 Substituted aromatic groups having 6-20 carbon atoms; or unsubstituted or substituted with one or more substituents R. 0 Substituted heteroaromatic groups having 5-20 ring atoms; R 0 Each occurrence is independently selected from one or more combinations of -D, halogen, cyano, nitro, straight-chain alkyl with 1-10 carbon atoms, branched alkyl with 3-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, aromatic group with 6-20 carbon atoms, and heteroaromatic group with 5-20 cyclic atoms.

2. The triazine-containing organic compound according to claim 1, characterized in that: The triazine-containing organic compounds have structures as shown in any of the general formulas (II-1)-(II-6): 。 3. The triazine-containing organic compound according to claim 1 or 2, characterized in that: R1 is selected from any of the following groups: ； Where: * indicates a connection site.

4. The triazine-containing organic compound according to claim 1 or 2, characterized in that: The L1 and L2 are independently selected from single bonds or any of the following groups: ； Where: m3 is selected from 0, 1, 2, 3 or 4; m4 is selected from 0, 1, 2, 3, 4, 5 or 6.

5. The triazine-containing organic compound according to claim 1 or 2, characterized in that: The Ar1 and Ar2 are independently selected from any of the following groups: ； Where: m5 is selected from 0, 1, 2, 3, 4 or 5; m6 is selected from 0, 1, 2, 3 or 4; m7 is selected from 0, 1, 2, 3, 4, 5, 6 or 7.

6. The triazine-containing organic compound according to claim 1, characterized in that: The R 0 Each occurrence is independently selected from one or a combination of at least two of the following: -D, -F, -Cl, cyano, nitro, unsubstituted or -D-substituted methyl, unsubstituted or -D-substituted ethyl, unsubstituted or -D-substituted n-propyl, unsubstituted or -D-substituted isopropyl, unsubstituted or -D-substituted n-butyl, unsubstituted or -D-substituted tert-butyl, unsubstituted or -D-substituted cyclohexyl, unsubstituted or -D-substituted adamantyl, unsubstituted or -D-substituted phenyl, unsubstituted or -D-substituted biphenyl, unsubstituted or -D-substituted naphthyl, and unsubstituted or -D-substituted pyridyl.

7. The triazine-containing organic compound according to claim 1, characterized in that: The triazine-containing organic compound is selected from any of the following structures: 。 8. An organic electroluminescent device, the organic electroluminescent device comprising a cathode, an anode, and a light-emitting layer located between the cathode and the anode, characterized in that: The light-emitting layer comprises a triazine-containing organic compound as described in any one of claims 1-7.

9. The organic electroluminescent device according to claim 8, characterized in that: The light-emitting layer comprises a first host material H1 and a second host material H2, wherein the first host material H1 is selected from triazine-containing organic compounds as described in any one of claims 1-7, and the second host material H2 is selected from hole-transporting host materials.

10. The organic electroluminescent device according to claim 9, characterized in that: The second main material H2 is selected from any of the following structures: 。

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