Tetradentate ring metal platinum (II) complex, electronic device and application of tetradentate ring metal platinum (II) complex

Abstract

The invention belongs to the technical field of preparation of organic electroluminescent materials, and particularly relates to a tetradentate ring metal platinum (II) complex, an electronic device and application of the tetradentate ring metal platinum (II) complex. The invention provides a tetradentate platinum (II) complex obtained by introducing 2, 6-diisopropyl phenyl to different positions of carbazole, and the complex has a structure as shown in a formula (I). The introduction of 2, 6-diisopropyl phenyl reduces the interaction between molecules, the group has good solubility, so that the platinum complex has good spin-coating performance, and the provided compound has good chemical stability, can improve and balance the transport of holes and electrons, enables the energy transmission between a subject and an object to be more efficient, and has a good application prospect. Specifically, the compound or the composition provided by the invention is used for improving the current efficiency and prolonging the service life of the organic light-emitting device, and has a great application prospect in the fields of OLED display and illumination.

Description

Technical Field

[0001] This invention belongs to the field of organic electroluminescent material preparation technology, specifically relating to a tetradentate ring platinum(II) complex, electronic devices and their applications. Background Technology

[0002] Organic light-emitting diodes (OLEDs) are a new generation of full-color display and lighting technology. Compared to liquid crystal displays (LCDs), which suffer from slow response times, narrow viewing angles, the need for backlighting, and high energy consumption, OLEDs, as self-emissive devices, do not require backlighting, making them energy-efficient. They also feature low driving voltage, fast response times, high resolution and contrast, wide viewing angles, and excellent low-temperature performance. OLED devices can be made thinner and can be fabricated into flexible structures. Furthermore, they offer advantages such as low production costs, simple manufacturing processes, and the ability to be mass-produced. Therefore, OLEDs have broad and enormous application prospects in high-end electronics and aerospace. With increasing investment, further research and development, and upgrades to production equipment, OLEDs have a very wide range of application scenarios and development prospects in the future.

[0003] The core of OLED development lies in the design and development of luminescent materials. Currently, almost all OLED devices utilize a host-guest luminescence mechanism in their luminescent layers. This involves doping a host material with a guest luminescent material. The host material generally has a higher energy level than the guest material, transferring energy from the host to the guest material, thus exciting the guest material to emit light. Commonly used organic phosphorescent guest materials are typically heavy metal atoms such as iridium(III), platinum(II), and Pd(II). Commonly used phosphorescent organic materials, mCBP (3,3′-bis(9-carbazolyl)-biphenyl) and 2,6-mCPy (2,6-bis(9-carbazolyl)-pyridine), possess high efficiency and high triplet energy levels. When used as organic materials, triplet energy can be effectively transferred from the luminescent organic material to the guest phosphorescent material. However, due to the easy transport of holes and the difficult flow of electrons in mCBP, and the poor hole transport in 2,6-mCPy, the charge imbalance in the luminescent layer results in reduced device current efficiency. Furthermore, the number of iridium(III) complex molecules used in current heavy metal phosphorescent organic complexes is limited. The abundance of platinum in the Earth's crust and its annual global production are both approximately ten times that of iridium. IrCl3, used to prepare iridium(III) complex phosphorescent materials, is a significant resource. .The price of H2O is also much higher than that of PtCl2 used to prepare platinum(II) complex phosphorescent materials. Furthermore, the preparation of iridium(III) complex phosphorescent materials involves four steps: iridium(III) dimer formation, iridium(III) intermediate ligand exchange, synthesis of mer-iridium(III) complexes, and isomerization from mer- to fac-iridium(III) complexes. This significantly reduces the overall yield and the cost of the raw material IrCl3. . The increased utilization of H2O raises the preparation cost of iridium(III) complex phosphorescent materials. In contrast, the preparation of platinum(II) complex phosphorescent materials involves only the final step of ligand metallization design of platinum salts, resulting in high platinum element utilization and further reducing the preparation cost. In summary, the preparation cost of platinum(II) complex phosphorescent materials is significantly lower than that of iridium(III) complex phosphorescent materials. However, the development of platinum complex materials and devices still faces some technical challenges, and improving device efficiency and lifetime remains a crucial research issue. Therefore, the development of novel phosphorescent platinum(II) complexes is urgently needed. Summary of the Invention

[0004] In view of this, the object of the present invention is to provide a tetradentate ring platinum(II) complex, an electronic device, and its applications. The tetradentate ring platinum(II) complex of the present invention, as a guest phosphorescent material for the light-emitting layer, can enable the device to possess excellent performance. Combining it with specific host materials can improve the current efficiency of electronic devices, especially organic electroluminescent devices, improve device lifetime, and also reduce the operating voltage of components.

[0005] This invention provides a tetradentate ring platinum(II) complex having a structure as shown in formula (I):

[0006]

[0007] In equation (I), R 1 -R 6 Each can be independently represented as unsubstituted, monosubstituted, disubstituted, trisubstituted, tetrasubstituted, or maximum number of substituted substances;

[0008] R 1 R 2 R 3 R 4 R 5 and R 6Each of the following is independently selected from one or more of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1–C30 alkyl, substituted or unsubstituted C3–C30 cycloalkyl, substituted or unsubstituted C3–C30 heterocycloalkyl, C1–C30 alkoxy, substituted or unsubstituted C6–C60 aryl, substituted or unsubstituted C5–C60 heteroaryl, substituted or unsubstituted C6–C60 aryloxy, mono- or di(C1–C30 alkyl)amino, mono- or di(substituted or unsubstituted C6–C60 aryl)amino, C1–C30 alkylsilyl, and C6–C60 arylsilyl; when substituted, each of the substituted is independently selected from one or more of hydrogen, deuterium, halogen, C1–C30 alkyl, C3–C30 cycloalkyl, C6–C60 aryl, and C5–C60 heteroaryl.

[0009] Preferably, the R 1 R 2 R 3 R 4 R 5 and R 6 Each is independently selected from hydrogen, deuterium, CD3, F, CF3, CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isohexyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantane. One or more of the following: alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, tetrahydronaphthyl, tert-butylphenyl, pyridyl, quinolinyl, dimethylfluorenyl, carbazole, dibenzofuranyl, dibenzothiopheneyl, trimethylsilyl, triarylsilyl, methoxy, phenothiazinyl, phenotoxazinyl, dimethylacridyl, N-phenylcarbazoleyl, and diarylamino; the above substituents may be further substituted by deuterium, F, methyl, ethyl, isopropyl, or tert-butyl.

[0010] R 1 R 2 R 3 R 4 R 5 R 6 Each can independently fuse with adjacent substitution sites to form a cyclic structure.

[0011] More preferably, the tetradentate cyclic platinum(II) complex is selected from any one of the following chemical structures, where "D" represents deuterium:

[0012]

[0013]

[0014]

[0015]

[0016]

[0017]

[0018]

[0019]

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

[0027]

[0028]

[0029]

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[0039]

[0040]

[0041]

[0042]

[0043]

[0044]

[0045]

[0046]

[0047]

[0048]

[0049] Furthermore, the present invention also provides the application of the tetradentate ring platinum (II) complex having the structure shown in formula (I) above in the fabrication of electronic devices.

[0050] Furthermore, the electronic devices include organic light-emitting diodes (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), organic optical detectors, organic photosensors, organic field quenching devices (O-FQDs), light-emitting electrochemical cells (LECs), and organic laser diodes (O-lasers).

[0051] In another aspect, the present invention also provides an organic electroluminescent device comprising a cathode, an anode, and an organic functional layer therebetween; the organic functional layer comprising a tetradentate ring platinum (II) complex having the structure shown in formula (I) above.

[0052] Furthermore, the organic functional layer includes a light-emitting layer containing a tetradentate ring platinum (II) complex having the structure shown in formula (I) as described above.

[0053] Furthermore, the light-emitting layer also contains a fluorescent dopant material; the fluorescent dopant material is preferably a boron-containing organic luminescent material.

[0054] In another aspect, the present invention also provides an organic optoelectronic device comprising: a substrate layer; a first electrode on the substrate; an organic light-emitting functional layer on the first electrode; and a second electrode on the organic light-emitting functional layer; wherein the organic light-emitting functional layer comprises a tetradentate ring platinum(II) complex having the structure shown in formula (I) above. For example, the platinum(II) complex can be included as a light-emitting material in the organic light-emitting functional layer.

[0055] Furthermore, the organic light-emitting functional layer also contains any one or more fluorescent doping materials, wherein the fluorescent doping material is preferably a boron-containing organic luminescent material, and more preferably a phosphorus-sensitive boron-containing compound.

[0056] In this invention, organic optoelectronic devices can be fabricated by depositing metals or conductive oxides and their alloys onto a substrate using methods such as sputtering, electron beam evaporation, and vacuum deposition to form the anode. A hole injection layer, hole transport layer, light-emitting layer, air-blocking layer, and electron transport layer are then sequentially deposited onto the surface of the anode, followed by the deposition of the cathode. Alternatively, organic electroluminescent devices can be fabricated by depositing the cathode, organic layer, and anode onto a substrate in that order. The organic layer can also include a multi-layer structure comprising a hole injection layer, a hole transport layer, a light-emitting layer, a hole-blocking layer, and an electron transport layer. In this invention, the organic layer is prepared using polymer materials via solvent engineering (spin-coating, tape-casting, doctor-blading, screen-printing, inkjet printing, or thermal imaging, etc.) instead of evaporation methods, which can reduce the number of device layers.

[0057] The present invention also provides a composition comprising a tetradentate cyclic platinum(II) complex having the structure shown in formula (I) above. Preferably, the composition further comprises a fluorescent dopant material, which is preferably a boron-containing organic luminescent material, and more preferably a phosphorescently sensitizable boron-containing compound.

[0058] The present invention also provides a formulation comprising a tetradentate cyclic platinum(II) complex having the structure shown in formula (I) as described above and at least one solvent. The solvent is not particularly limited and may be any solvent well known to those skilled in the art, such as unsaturated hydrocarbon solvents, halogenated saturated hydrocarbon solvents, halogenated unsaturated hydrocarbon solvents, ether solvents, or ester solvents; wherein the unsaturated hydrocarbon solvent is toluene, xylene, mesitylene, tetrahydronaphthalene, n-butylbenzene, sec-butylbenzene, or tert-butylbenzene; the halogenated saturated hydrocarbon solvent is carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, or bromocyclohexane; the halogenated unsaturated hydrocarbon solvent is chlorobenzene, dichlorobenzene, or trichlorobenzene; the ether solvent is tetrahydrofuran or tetrahydropyran; and the ester solvent is an alkyl benzoate ester.

[0059] The present invention also provides a display or lighting device comprising one or more of the organic optoelectronic devices described above.

[0060] Compared with the prior art, the beneficial effects of the present invention are:

[0061] This invention reduces intermolecular interactions by introducing 2,6-diisopropylphenyl, resulting in a low shoulder peak and improved luminescent purity. Furthermore, the excellent solubility of this group gives the platinum complex excellent spin-coating properties. The materials involved in this invention all possess excellent chemical and thermal stability, facilitating the fabrication of vapor-deposited OLED devices. When combined with fluorescent doping materials, they can balance hole and electron transport, making energy transfer between the host and guest more efficient. Organic electroluminescent devices fabricated using the compounds of this invention as the luminescent layer show significant improvements in current efficiency and lifetime, and a marked reduction in turn-on voltage. In particular, their application in conjunction with phosphorus-sensitized boron-containing compounds can further enhance the luminescent purity of the device. Attached Figure Description

[0062] Figure 1 This is the room temperature emission spectrum of platinum complexes BD-02 and Pt25 in dichloromethane solution;

[0063] Figure 2 This is the room temperature emission spectrum of platinum complexes BD-02 and Pt26 in dichloromethane solution;

[0064] Figure 3 This is the room temperature emission spectrum of platinum complexes BD-02 and Pt529 in dichloromethane solution;

[0065] Figure 4 This is the room temperature emission spectrum of platinum complexes BD-02 and Pt530 in dichloromethane solution;

[0066] Figure 5This is the room temperature emission spectrum of platinum complexes BD-02 and Pt121 in dichloromethane solution;

[0067] Figure 6 This is a comparison of the room-temperature emission spectra of platinum complex BD-02 and Pt complexes Pt25, Pt26, Pt529, Pt530, and Pt121 in dichloromethane. Detailed Implementation

[0068] The present invention will now be described in detail. The descriptions of the constituent elements described below are sometimes based on representative embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples.

[0069] The term "substituted" as used in this invention is intended to encompass all permissible substituents of organic compounds. In a broad sense, permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, and aromatic and non-aromatic substituents of organic compounds. Illustrative substituents include, for example, those described below. For a suitable organic compound, permissible substituents may be one or more, the same or different. For the purposes of this invention, heteroatoms (e.g., nitrogen) may have hydrogen substituents and / or any permissible substituent of the organic compound described herein, satisfying the valence bond of that heteroatom. This invention is not intended to limit in any way to permissible substituents of organic compounds. Similarly, the terms "substituted" or "substituted with" implicitly include the condition that such substitution conforms to the permissible valence bond of the substituted atom and the substituent, and that the substitution results in a stable compound (e.g., a compound that does not spontaneously undergo transformations (e.g., by rearrangement, cyclization, elimination, etc.)). It is also expected that, in some respects, unless explicitly stated otherwise, individual substituents can be further optionally substituted (i.e., further substituted or unsubstituted).

[0070] The "R1", "R2", "R3"... "R" used in this invention n The group “” (where n is an integer) may independently have one or more of the groups listed above. For example, if R1 is a straight-chain alkyl group, then one hydrogen atom of the alkyl group may be optionally substituted with a hydroxyl, alkoxy, alkyl, halogen, etc. Depending on the chosen group, the first group may be incorporated into the second group, or alternatively, the first group may be dangling, i.e., attached to the second group. For example, for the phrase “alkyl group containing an amino group”, the amino group may be incorporated into the backbone of the alkyl group. Alternatively, the amino group may be attached to the backbone of the alkyl group. The nature of the chosen group will determine whether the first group is embedded in or attached to the second group.

[0071] As used in this invention, the term "alkyl" refers to a branched or unbranched saturated hydrocarbon group with 1 to 30 carbon atoms. Preferred alkyl groups are alkyl groups containing 1 to 24 carbon atoms, more preferably 1 to 12 carbon atoms. Examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, hexyl, heptyl, semi-alkyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, etc. The alkyl group may be branched or unbranched. It may also be substituted or unsubstituted. For example, the alkyl group may be substituted with one or more groups, including but not limited to the optionally substituted alkyl, cycloalkyl, alkoxy, amino, halogen, hydroxyl, nitro, silyl, sulfoxo, or mercapto groups described in this invention.

[0072] This practice is also applied to other groups described in this invention. That is, when a term such as "cycloalkyl" refers to both an unsubstituted and a substituted cycloalkyl moiety, the substituted moiety may be specifically identified in this invention; for example, a specifically substituted cycloalkyl moiety may be referred to as, for example, "alkylcycloalkyl". Similarly, a substituted alkoxy moiety may be specifically referred to as, for example, "halogenated alkoxy".

[0073] As used in this invention, the term "cycloalkyl" refers to a non-aromatic carbon-based ring consisting of at least three carbon atoms. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclononyl, adamantyl, etc. The term "heterocyclic alkyl" is a class of cycloalkyl groups as defined above and is included in the meaning of the term "cycloalkyl," wherein at least one ring carbon atom is substituted by a heteroatom, such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus. The cycloalkyl and heterocyclic alkyl groups may be substituted or unsubstituted. The cycloalkyl and heterocyclic alkyl groups may be substituted with one or more groups, including but not limited to alkyl, cycloalkyl, alkoxy, amino, halogen, hydroxyl, nitro, silyl, sulfo-oxo, or mercapto groups as described in this invention.

[0074] As used in this invention, the term "aryl" refers to any carbon-based aromatic group containing 6 to 60 carbon atoms, preferably aryl groups containing 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms. The carbon-based aromatic groups include, but are not limited to, phenyl, naphthyl, phenyl, biphenyl, phenoxyphenyl, anthracene, phenanthrene, etc. The term "aryl" also includes "heteroaryl," which is defined as a group containing an aromatic group having at least one heteroatom introduced into the ring of the aromatic group. Examples of heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, silicon, and phosphorus. Aryl groups may be substituted or unsubstituted. Aryl groups may be substituted with one or more groups, including, but not limited to, the alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxyl, ester, halogen, hydroxyl, carbonyl, azide, nitro, silyl, sulfo-oxo, or mercapto groups described in this invention. The term "biaryl" refers to a specific type of aryl group and is included in the definition of "aryl". A biaryl group is two aryl groups that are bonded together by a fused ring structure, as in naphthalene, or two aryl groups that are linked by one or more carbon-carbon bonds, as in biphenyl.

[0075] In the compounds mentioned in this invention, unless explicitly specified, for example, that adjacent substituents can optionally connect to form a ring, adjacent substituents in the compound cannot connect to form a ring. In the compounds mentioned in this disclosure, the optional connection of adjacent substituents to form a ring includes both cases where adjacent substituents can connect to form a ring and cases where adjacent substituents do not connect to form a ring. When adjacent substituents can optionally connect to form a ring, the formed ring can be a monocyclic or polycyclic ring (including spirocyclic, bridged, fused rings, etc.), as well as an alicyclic, heterocyclic, aromatic, or heteroaromatic ring. The carbon atom is preferably C3 to C30, more preferably C3 to C18. More preferably, in this description, C3 to C6. Adjacent substituents can refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom and substituents bonded to carbon atoms directly bonded to each other.

[0076] The term "amine" or "amino" used in this invention is derived from the formula -NR 1 R 2 It means that R 1 and R 2 It can be independently selected from hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, ynyl, cycloynyl, aryl or heteroaryl.

[0077] The compounds disclosed herein can exhibit desired properties and have emission and / or absorption spectra that can be tuned by selecting suitable ligands. On the other hand, the invention excludes any one or more compounds, structures, or portions thereof specifically described herein.

[0078] The compounds of the present invention can be prepared using a variety of methods, including but not limited to those described in the examples provided herein. This application can be more readily understood by referring to the following detailed description and the examples contained therein.

[0079] Before disclosing and describing the compounds, devices, and / or methods of the present invention, it should be understood that they are not limited to specific synthetic methods (otherwise indicated) or specific reagents (otherwise indicated), as these are, of course, subject to variation. It should also be understood that the terminology used in this invention is for descriptive purposes only and is not intended to be limiting. While any methods and materials similar to or equivalent to those described in this invention may be used in this practice or experiment, exemplary methods and materials are described below. All raw materials and solvents used in the synthetic examples are commercially available unless otherwise specified, and the solvents were used directly without further processing.

[0080] The substrate described in this invention can be any substrate typically used in organic optoelectronic devices. It can be a glass or transparent plastic substrate, an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance, and their applications vary depending on their properties. As materials for the hole injection layer, hole transport layer, and electron injection layer, any known materials used in OLED devices can be selected, and this invention does not impose specific limitations.

[0081] Synthesis Examples

[0082] The examples of compound synthesis, composition, devices, or methods below are intended to provide a general approach to the industry and are not intended to limit the scope of this patent. While we have striven to ensure the accuracy of data (quantities, temperatures, etc.) mentioned in the patent, some errors may still exist. Unless otherwise specified, weighings are performed separately at 25°C or room temperature, and at near-normal pressure.

[0083] The examples below provide methods for preparing novel compounds, but the preparation of such compounds is not limited to these methods. In this field of expertise, since the compounds protected in this invention are easily modified and prepared, their preparation can be carried out using the methods listed below or other methods. The examples below are merely illustrative and are not intended to limit the scope of this patent. Temperature, catalyst, concentration, reactants, and reaction process can all be varied to select different conditions for preparing the compounds with different reactants.

[0084] 1 H NMR (500MHz), 1 H NMR (400MHz), 13 C10 NMR (125 MHz) spectra were measured on an ANANCE III (500 M) nuclear magnetic resonance spectrometer; unless otherwise specified, DMSO or CDCl3 containing 0.1% TMS was used as the solvent for all NMR measurements. 1 When using CDCl3 as the solvent in HNMR spectroscopy, TMS (δ = 0.00 ppm) is used as the internal standard; when using DMSO as the solvent, TMS (δ = 0.00 ppm), residual DMSO peak (δ = 2.50 ppm), or residual water peak (δ = 3.33 ppm) are used as the internal standard. 13 In the 10⁻⁶ C NMR spectra, CDCl₃ (δ = 77.00 ppm) or DMSO (δ = 39.52 ppm) were used as internal standards. HPLC-MS was performed on an Agilent 6210TOF LC / MS mass spectrometer; HRMS spectra were performed on an Agilent 6210TOF LC / MS liquid chromatography-time-of-flight mass spectrometer. 1 In the H NMR spectral data: s = singlet, d = doublet, t = triplet, q = quartet, p = quintet, m = multiplet, br = broad.

[0085] Synthetic route

[0086] Example 1: The synthesis route of Pt25, a phosphorescent material composed of a tetradentate ring platinum(II) complex, is as follows:

[0087]

[0088] Synthesis of intermediate tBu-NH2: p-tert-butylaniline (20.00 g, 134.01 mmol, 1.0 equiv) and dichloromethane solvent (200 mL) were added sequentially to a dry three-necked flask equipped with a magnetically stirred rotor. After dissolving, the mixture was cooled to below 0 °C and N-bromosuccinimide (28.62 g, 160.81 mmol, 1.2 equiv) was added. The mixture was then transferred to room temperature and stirred overnight. The reaction was monitored by TCL until it was basically complete. To neutralize excess N-bromosuccinimide, a saturated solution of sodium thiosulfate (2.12 g, 13.4 mmol, 0.1 equiv) was added to the reaction solution. Extraction was then performed with 100 mL of dichloromethane, repeated twice. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, and mixed with silica gel. The crude product was purified by silica gel column chromatography with petroleum ether – petroleum ether / ethyl acetate (V / V) = 20 / 1, yielding 23.69 g of tBu-NH2, a brown liquid, with a yield of 77%.

[0089] Synthesis of intermediate tBu-NO2-NH2: tBu-NH2 (23.69 g, 103.83 mmol, 1.0 equiv) and N,N-dimethylformamide (300 mL) were added to a dry three-necked flask equipped with a magnetic stirrer. After dissolving, the mixture was cooled to below 0°C, and 60% sodium hydride (12.47 g, 311.49 mmol, 3.0 equiv) was slowly added. After stirring at low temperature for half an hour, o-fluoronitrobenzene (19.05 g, 134.98 mmol, 1.3 equiv) was added. The mixture was then transferred to room temperature and stirred overnight. The reaction was monitored by TCL TLC to indicate that the reaction was essentially complete. Deionized water and ethyl acetate (100 mL) were added to the system for extraction, which was repeated twice. Then, the system was extracted with saturated brine. The organic phases were combined, dried with anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, and mixed with silica gel. The crude product was purified by silica gel column chromatography with petroleum ether as the eluent to obtain 35.17 g of tBu-NO2-NH2, a yellow liquid, with a yield of 97%.

[0090] Synthesis of intermediate tBu-Br-NH2: tBu-NO2-NH2 (35.00 g, 100.22 mmol, 1.0 equiv), stannous chloride dihydrate (90.46 g, 400.88 mmol, 4.0 equiv), ethanol (100 mL), and ethyl acetate (100 mL) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging the nitrogen gas three times with a water pump, the reaction mixture was placed in an oil bath, heated to 78 °C, and stirred for 12 hours. The reaction was then monitored by TCL spotting to indicate that the reaction was essentially complete. Cool to room temperature, add saturated sodium bicarbonate solution to neutralize until no more gas is produced in the reaction, add ethyl acetate (100 mL) for extraction, repeat twice, combine the organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, mix with silica gel, and purify the crude product by silica gel column chromatography with petroleum ether / ethyl acetate (V / V) = 20 / 1 to obtain tBu-Br-NH2, a red liquid of 22.11 g, yield 69%.

[0091] Synthesis of intermediate tBu-Ph-NH2: tBu-Br-NH2 (22.11 g, 69.26 mmol, 1.0 equiv), phenylboronic acid (16.89 g, 138.52 mmol, 2.0 equiv), tetrakis(triphenylphosphine)palladium (1.60 g, 1.39 mmol, 0.02 equiv), and potassium carbonate (19.14 g, 138.52 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, 1,4-dioxane (200 mL) and deionized water (50 mL) were injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 90 °C, and stirred for 12 hours. The reaction was then monitored by TCL (Temperature Computed Tomography) to indicate that the reaction was essentially complete. Cool to room temperature, add deionized water and ethyl acetate (100 mL) for extraction, repeat twice, combine organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, mix with silica gel, and purify the crude product by silica gel column chromatography with petroleum ether / ethyl acetate (V / V) = 40 / 1–5 / 1 to obtain tBu-Ph-NH2, 14.58 g white solid, yield 88%. 1H NMR(500MHz,DMSO-d6)δ(ppm):1.27(s,9H),4.71(s,2H),5.85(s,1H),6.48(td, J=7.5,1.5Hz,1H),6.68(dd,J=7.5,1.5Hz,1H),6.71(d,J=8.5Hz,1H),6.74(td,J =8.0,1.5Hz,1H),6.85(dd,J=8.0,1.0Hz,1H),7.15(d,J=2.0Hz,1H),7.20(dd,J= 8.5,2.0Hz,1H),7.33(t,J=7.5Hz,1H),7.43(t,J=8.0Hz,2H),7.52–7.54(m,2H).

[0092]

[0093] Synthesis of intermediate NO2-Cl-1: 2-Bromo-4-chloro-1-nitrobenzene (50.00 g, 211.46 mmol, 1.0 equiv), p-methoxyphenylboronic acid (33.74 g, 222.03 mmol, 1.05 equiv), tetrakis(triphenylphosphine)palladium (4.89 g, 4.23 mmol, 0.02 equiv), and potassium carbonate (58.45 g, 422.92 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, 1,4-dioxane (500 mL) and deionized water (125 mL) were injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 80 °C, and stirred for 17 hours. TCL plate testing showed the reaction was essentially complete. Cool to room temperature, add deionized water and ethyl acetate (100 mL) for extraction, repeat twice, combine organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, mix with silica gel, and purify the crude product by silica gel column chromatography with petroleum ether / dichloromethane (V / V) = 20 / 1–2 / 1 to obtain NO2-Cl-1, a yellow solid of 44.50 g, yield 85%.

[0094] Synthesis of intermediate NO2-iPr-1: NO2-Cl-1 (44.50 g, 169.18 mmol, 1.0 equiv), iPr-Bpin (73.15 g, 253.77 mmol, 1.5 equiv), tris(dibenzylacetone)dipalladium (3.10 g, 3.38 mmol, 0.02 equiv), tricyclohexylphosphine (1.90 g, 6.77 mmol, 0.04 equiv), and sodium hydroxide (13.53 g, 338.36 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging the flask three times with nitrogen using an oil pump, 1,4-dioxane (500 mL) and deionized water (125 mL) were injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 100 °C, and stirred for 12 hours. The reaction was then monitored by TCL (Temperature Computed Tomography) to indicate that the reaction was essentially complete. Cool to room temperature, add deionized water and ethyl acetate (100 mL) for extraction, repeat twice, combine organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, mix with silica gel, and purify the crude product by silica gel column chromatography with petroleum ether / ethyl acetate (V / V) = 100 / 1–40 / 1 to obtain NO2-iPr-1, 52.72 g of yellow solid, yield 80%.

[0095] Synthesis of intermediate NH-iPr-1: NO2-iPr-1 (52.72 g, 135.35 mmol, 1.0 equiv) and triphenylphosphine (106.50 g, 406.05 mmol, 3.0 equiv) were added to a dry round-bottom flask equipped with a magnetically stirred rotor. After purging with nitrogen three times using an oil pump, o-dichlorobenzene (500 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 180 °C, and stirred for 24 hours. The reaction was monitored by TCL spotting to indicate near-complete reaction. After cooling to room temperature, the solvent was removed by vacuum concentration. The sample was mixed with silica gel, and the crude product was purified by silica gel column chromatography with eluent: petroleum ether / ethyl acetate (V / V) = 20 / 1–6 / 1, yielding NH-iPr-1, 34.36 g white solid, yield 71%.

[0096] Synthesis of intermediate iPr-OMe-1: NH-iPr-1 (34.36 g, 96.11 mmol, 1.0 equiv), 4-tert-butyl-2-chloropyridine (19.57 g, 115.33 mmol, 1.2 equiv), tris(dibenzylacetone)dipalladium (8.88 g, 0.97 mmol, 0.01 equiv), 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (2.37 g, 5.77 mmol, 0.06 equiv), and sodium tert-butoxide (18.47 g, 192.22 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, toluene (400 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 110 °C, and stirred for 12 hours. The reaction was monitored by TCL TLC to indicate that it was essentially complete. Cool to room temperature, add deionized water and ethyl acetate (100 mL) for extraction, repeat twice, combine organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, mix with silica gel, and purify the crude product by silica gel column chromatography with eluent: petroleum ether / ethyl acetate (V / V) = 60 / 1–40 / 1, to obtain iPr-OMe-1, white solid 40.56 g, yield 86%.

[0097] Synthesis of intermediate iPr-OH-1: iPr-OMe-1 (40.56 g, 82.66 mmol, 1.0 equiv), hydrobromic acid (100 mL), and acetic acid (10 mL) were added to a dry round-bottom flask equipped with a magnetically stirred rotor. The reaction mixture was placed in an oil bath, heated to 120 °C, and stirred for 24 hours. The reaction was monitored by TCL spotting to indicate near-complete reaction. The mixture was cooled to room temperature, and the solvent was removed by vacuum distillation. The resulting mixture was neutralized to neutral by adding saturated sodium bicarbonate solution, and extracted with ethyl acetate (100 mL). This process was repeated twice. The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography with petroleum ether / ethyl acetate (V / V) = 20 / 1–1 / 1 to give iPr-OH-1, 35.07 g of white solid, yield 89%. 1H NMR (500MHz, CDCl3) δ (ppm): 1.08 (d, J = 7.0Hz, 6H), 1.11 (d, J = 6.5Hz, 6H), 1.43 (s, 9H), 2.70–2.78 ( m,2H),5.95(s,1H),6.79(dd,J=8.0,2.0Hz,1H),7.16(dd,J=8.5,1.5Hz,1H),7.24(s,1H),7.25(s, 1H),7.30(d,J=2.0Hz,1H),7.32(dd,J=5.0,1.5Hz,1H),7.34(t,J=7.5Hz,1H),7.68(d,J=1.5Hz,1H ),7.73(d,J=8.0Hz,1H),7.77(d,J=1.0Hz,1H),7.87(d,J=8.5Hz,1H),8.62(dd,J=5.0,0.2Hz,1H).

[0098] Synthesis of intermediate iPr-Cl-1: iPr-OH-1 (26.01 g, 54.57 mmol, 1.0 equiv), m-chlorobromobenzene (12.54 g, 65.48 mmol, 1.2 equiv), cuprous iodide (2.08 g, 10.91 mmol, 0.2 equiv), 2-pyridinecarboxylic acid (2.69 g, 21.83 mmol, 0.4 equiv), and potassium phosphate (23.17 g, 109.14 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, DMSO (170 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 100 °C, and stirred for 16 hours. TCL TLC monitoring showed the reaction was essentially complete. Cool to room temperature, add deionized water and ethyl acetate (100 mL) for extraction, repeat twice, combine organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, mix with silica gel, and purify the crude product by silica gel column chromatography with petroleum ether / ethyl acetate (V / V) = 40 / 1–20 / 1 to obtain iPr-Cl-1, 17.51 ​​g white solid, yield 53%. 1HNMR (500MHz, CDCl3) δ (ppm): 1.08 (d, J = 7.0Hz, 6H), 1.12 (d, J = 7.0Hz, 6H), 1.38 (s, 9H),2.70–2.78(m,2H),6.95(ddd,J=8.5,,2.5,1.0Hz,1H),7.03–7.06(m,3H),7.22– 7.26(m,4H),7.31(dd,J=5.5,1.5,Hz,1H),7.39(t,J=7.5Hz,1H),7.42(d,J=2.0Hz,1 H),7.61(d,J=1.0Hz,1H),7.86(m,2H),8.06(d,J=8.5Hz,1H),8.62(d,J=5.5Hz,1H).

[0099] Synthesis of intermediate tBu-iPr-Cl-1: iPr-OH-1 (8.64 g, 18.13 mmol, 1.0 equiv), 1-bromo-3-tert-butyl-5-chlorobenzene (6.73 g, 27.20 mmol, 1.5 equiv), cuprous iodide (691 mg, 3.63 mmol, 0.2 equiv), 2-pyridinecarboxylic acid (893 mg, 7.25 mmol, 0.4 equiv), and potassium phosphate (7.70 g, 36.26 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, DMSO (100 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 100 °C, and stirred for 16 hours. TCL (ThinPrep) monitoring showed the reaction was essentially complete. Cool to room temperature, add deionized water and ethyl acetate (100 mL) for extraction, repeat twice, combine organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, mix with silica gel, and purify the crude product by silica gel column chromatography with petroleum ether / ethyl acetate (V / V) = 40 / 1–20 / 1 to obtain tBu-iPr-Cl-1, 9.34 g white solid, yield 80%. 1H NMR(500MHz,CDCl3)δ(ppm):1.08(d,J=7.0Hz,6H),1.12(d,J=7.0Hz,6H),1.28(s,9H),1.37(s,9H),2.69–2.77(m,2H),6.80(t,J=2.0Hz,1H),7.03–7.05(m,2H),7.08(t,J=1.5Hz,1H),7.22–7.25(m,2H),7.26(s,2H),7.30(dd,J=5.5,2.0Hz,1H),7.39(t,J=7.5Hz,1H),7.42(d,J=2.0Hz,1H),7.61(d,J=1.5Hz,1H),7.85(d,J=6.0Hz,1H),7.86(s,1H),8.04(d,J=8.5Hz,1H),8.61(d,J=5.5Hz,1H).

[0100]

[0101] Synthesis of ligand L25: iPr-Cl-1 (1.00 g, 1.70 mmol, 1.0 equiv), tBu-Ph-NH2 (592 mg, 1.87 mmol, 1.1 equiv), tris(dibenzylacetone)palladium (47 mg, 0.05 mmol, 0.03 equiv), 2-(dicyclohexylphosphine)-3,6-dimethoxy-2,4,6-tri-1-propyl-11-biphenyl (55 mg, 0.10 mmol, 0.06 equiv), and sodium tert-butoxide (327 mg, 3.40 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, toluene (20 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 110 °C, and stirred for 4 hours. The reaction was then monitored by TCL (Temporary Chromatography-Based Logging) to indicate that the reaction was essentially complete. Cool to room temperature, extract with deionized water and ethyl acetate (100 mL), repeat twice, combine organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, mix with silica gel, and purify the crude product by silica gel column chromatography with eluent: petroleum ether / ethyl acetate (V / V) = 40 / 1–20 / 1, to obtain the intermediate diamine compound, 1.18 g white solid, yield 80%. Since this intermediate diamine compound is unstable, it was used directly in subsequent reactions. Add the intermediate diamine compound (1.18 g, 1.36 mmol, 1.0 equiv) and ammonium hexafluorophosphonate (443 mg, 2.72 mmol, 2.0 equiv) to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, inject triethyl orthoformate (10 mL) under nitrogen protection. Place the reaction mixture in an oil bath, heat to 75 °C and stir for half an hour. TCL TLC monitoring showed the reaction was essentially complete. The solvent was removed by vacuum concentration, and the sample was mixed with silica gel. The crude product was then purified by silica gel column chromatography with dichloromethane / methanol (V / V) = 100 / 1 as eluent to obtain L25, a white solid of 931 mg, with a yield of 67%. 1H NMR (500MHz, DMSO) δ (ppm): 1.03 (d, J = 7.0Hz, 6H), 1.06 (d, J = 7.0Hz, 6H), 1.33 (s, 9H), 1.41 (s, 9H) ),2.57–2.65(m,2H),7.13–7.19(m,4H),7.23–7.25(m,5H),7.37(t,J=8.0Hz,1H),7.41–7.45(m,3 H),7.49–7.55(m,4H),7.61(td,J=8.0,0.5Hz,1H),7.70(d,J=2.5Hz,1H),7.75–7.78(m,2H),7.8 0–7.86(m,4H),8.09(d,J=1.5Hz,1H),8.38(d,J=8.5Hz,1H),8.60(d,J=5.0Hz,1H),10.41(s,1H).

[0102] Synthesis of metallized Pt25: L25 (100 mg, 0.10 mmol, 1.0 equiv), (1,5-cyclooctadiene)platinum(II) chloride (36 mg, 0.11 mmol, 1.05 equiv), and sodium acetate (25 mg, 0.30 mmol, 3.0 equiv) were added to a dry round-bottom flask equipped with a magnetically stirred rotor. After purging with nitrogen three times using an oil pump, diethylene glycol dimethyl ether (2 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 150 °C, and stirred in the dark for two days, then cooled to room temperature. The solvent was removed by vacuum distillation. The crude product was purified by silica gel column chromatography with petroleum ether / dichloromethane (V / V) = 1 / 1 to give Pt25, 55 mg of yellow solid, yield 52%. 1HNMR(500MHz, CDCl3)δ(ppm),1.12–1.20(m,12H),1.19(s,9H),1.37(s,9H),2.75(hept,J=7.0Hz,1H),2.86(hept,J=7.0 Hz,1H),6.27(dd,J=6.5,2.0Hz,1H),6.85(s,1H),7.03(s,1H),7.17(d,J=7.5Hz,1H),7.21(dd,J=8.0,1.5Hz,1H),6.65– 7.25(br,3H),7.26–7.30(m,3H),7.34(t,J=7.5Hz,1H),7.42(t,J=8.0Hz,2H),7.26–7.48(br,4H),7.58–7.61(m,2H),7. 76(d,J=8.0Hz,1H),7.80–7.83(m,2H),7.86(d,J=1.0Hz,1H),7.95(d,J=1.5Hz,1H),8.08(d,J=8.0Hz,1H),9.00(s,1H).

[0103] Example 2: The synthesis route of Pt26, a phosphorescent material composed of tetradentate ring platinum(II) complex, is as follows:

[0104]

[0105] Synthesis of intermediate NO2-Cl-2: 2-Bromo-5-chloro-1-nitrobenzene (55.00 g, 232.61 mmol, 1.0 equiv), p-methoxyphenylboronic acid (38.88 g, 255.87 mmol, 1.1 equiv), tetrakis(triphenylphosphine)palladium (2.69 g, 2.33 mmol, 0.01 equiv), and potassium carbonate (64.30 g, 465.22 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, 1,4-dioxane (400 mL) and deionized water (100 mL) were injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 80 °C, and stirred for 17 hours. TCL TLC monitoring showed the reaction was essentially complete. Cool to room temperature, add deionized water and ethyl acetate (100 mL) for extraction, repeat twice, combine organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, mix with silica gel, and purify the crude product by silica gel column chromatography with petroleum ether / dichloromethane (V / V) = 20 / 1–2 / 1 to obtain NO2-Cl-2, a yellow solid of 42.90 g, yield 70%.

[0106] Synthesis of intermediate NO2-iPr-2: NO2-Cl-2 (42.90 g, 163.01 mmol, 1.0 equiv), iPr-Bpin (70.48 g, 244.52 mmol, 1.5 equiv), tris(dibenzylacetone)palladium (1.49 g, 1.63 mmol, 0.01 equiv), tricyclohexylphosphine (1.83 g, 6.52 mmol, 0.04 equiv), and sodium hydroxide (13.04 g, 326.02 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging the flask three times with nitrogen using an oil pump, 1,4-dioxane (400 mL) and deionized water (100 mL) were injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 100 °C, and stirred for 12 hours. The reaction was then monitored by TCL (Temperature Computed Tomography) to indicate that the reaction was essentially complete. Cool to room temperature, add deionized water and ethyl acetate (100 mL) for extraction, repeat twice, combine organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, mix with silica gel, and purify the crude product by silica gel column chromatography with petroleum ether / ethyl acetate (V / V) = 100 / 1–40 / 1 to obtain NO2-iPr-2, 22.00 g of yellow solid, yield 69%.

[0107] Synthesis of intermediate NH-iPr-2: NO2-iPr-2 (22.00 g, 56.48 mmol, 1.0 equiv) and triphenylphosphine (44.44 g, 169.44 mmol, 3.0 equiv) were added to a dry round-bottom flask equipped with a magnetically stirred rotor. After purging with nitrogen three times using an oil pump, o-dichlorobenzene (130 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 180 °C, and stirred for 24 hours. The reaction was monitored by TCL (ThinPrep) staining until essentially complete. After cooling to room temperature, the solvent was removed by vacuum concentration. The sample was mixed with silica gel, and the crude product was purified by silica gel column chromatography with petroleum ether / dichloromethane (V / V) = 3 / 1–1 / 1 to obtain NH-iPr-2, a white solid, 17.65 g, yield 87%. 1 H NMR (500MHz, CDCl3) δ (ppm): 1.10 (d, J = 7.0Hz, 12H), 2.66–2.74 (m, 2H), 3.93 (s, 3H), 6.90 (dd, J = 8.5, 2.5Hz, 1H), 6.94 (d, J = 2.5 Hz,1H),7.03(dd,J=8.0,1.5Hz,1H),7.19(d,J=0.5Hz,1H),7.24(s,1H),7.26(s,1H),7.39(t,J=7.5Hz,1H),7.97–8.01(m,3H).

[0108] Synthesis of intermediate iPr-OMe-2: NH-iPr-2 (17.65 g, 49.37 mmol, 1.0 equiv), 4-tert-butyl-2-chloropyridine (10.89 g, 164.18 mmol, 1.3 equiv), tris(dibenzylacetone)palladium (449 mg, 0.49 mmol, 0.01 equiv), 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (1.22 g, 2.96 mmol, 0.06 equiv), and sodium tert-butoxide (9.49 g, 98.74 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, toluene (150 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 110 °C, and stirred for 16 hours. The reaction was monitored by TCL TLC to indicate that the reaction was essentially complete. Cool to room temperature, add deionized water and ethyl acetate (100 mL) for extraction, repeat twice, combine organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, mix with silica gel, and purify the crude product by silica gel column chromatography with eluent: petroleum ether / ethyl acetate (V / V) = 60 / 1–20 / 1, to obtain iPr-OMe-2, 21.55 g white solid, yield 89%.

[0109] Synthesis of intermediate iPr-OH-2: iPr-OMe-2 (21.00 g, 42.80 mmol, 1.0 equiv), hydrobromic acid (300 mL), and acetic acid (30 mL) were added to a dry round-bottom flask equipped with a magnetically stirred rotor. The reaction mixture was placed in an oil bath, heated to 120 °C, and stirred for three days. The reaction was monitored by TCL spotting to indicate near-complete reaction. The mixture was cooled to room temperature, and the solvent was removed by vacuum distillation. The resulting mixture was neutralized to neutral by adding saturated sodium bicarbonate solution, and extracted with ethyl acetate (100 mL). This extraction was repeated twice. The organic phases were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography using dichloromethane / ethyl acetate (V / V) = 100 / 1–10 / 1, yielding iPr-OH-2, 16.00 g white solid, yield 78%. 1H NMR(500MHz, CDCl3)δ(ppm):1.07–1.09(m,12H),1.33(s,9H),2.68–2.76(m,2H),6.82( dd,J=8.0,2.0Hz,1H),7.08(dd,J=8.0,1.5Hz,1H),7.21(s,1H),7.23(s,1H),7.28(dd,J =5.5,2.0Hz,1H),7.33(d,J=2.0Hz,1H),7.36(t,J=8.0Hz,1H),7.39(d,J=0.5Hz,1H),7. 56(d,J=1.0Hz,1H),7.93(d,J=8.5Hz,1H),8.02(d,J=7.5Hz,1H),8.57(d,J=5.0Hz,1H).

[0110] Synthesis of intermediate iPr-Cl-2: iPr-OH-2 (10.77 g, 22.59 mmol, 1.0 equiv), m-chlorobromobenzene (6.49 g, 33.89 mmol, 1.5 equiv), cuprous iodide (861 mg, 4.52 mmol, 0.2 equiv), 2-pyridinecarboxylic acid (1.11 g, 9.04 mmol, 0.4 equiv), and potassium phosphate (9.59 g, 45.18 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, DMSO (120 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 100 °C, and stirred for 16 hours. TCL TLC monitoring showed the reaction was essentially complete. Cool to room temperature, add deionized water and ethyl acetate (100 mL) for extraction, repeat twice, combine organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, mix with silica gel, and purify the crude product by silica gel column chromatography with petroleum ether / ethyl acetate (V / V) = 40 / 1–20 / 1 to obtain iPr-Cl-2, 9.74 g white solid, yield 73%. 1HNMR(500MHz, CDCl3)δ(ppm):1.16(d,J=7.0Hz,6H),1.18(d,J=7.0Hz,6H),1.37(s,9H),2.76–2.8 4(m,2H),6.99(ddd,J=8.5,2.5,1.0Hz,1H),7.07–7.10(m,2H),7.12(dd,J=8.5,2.0Hz,1H),7.23(d d,J=8.0,1.5Hz,1H),7.27–7.33(m,4H),7.44(t,J=7.5,1H),7.60(d,J=2.0Hz,1H),7.60(d,J=0.45 Hz,1H),7.62(d,J=1.5Hz,1H),8.18(d,J=8.5Hz,1H),7.19(d,J=4.0Hz,1H),8.61(d,J=5.5Hz,1H).

[0111] Synthesis of intermediate tBu-iPr-Cl-2: iPr-OH-2 (10.00 g, 20.98 mmol, 1.0 equiv), 1-bromo-3-tert-butyl-5-chlorobenzene (7.80 g, 31.47 mmol, 1.5 equiv), cuprous iodide (800 mg, 4.20 mmol, 0.2 equiv), 2-pyridinecarboxylic acid (1.03 g, 8.39 mmol, 0.4 equiv), and potassium phosphate (8.90 g, 41.96 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, DMSO (180 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 100 °C, and stirred for 16 hours. TCL (ThinPrep) monitoring showed the reaction was essentially complete. Cool to room temperature, add deionized water and ethyl acetate (100 mL) for extraction, repeat twice, combine organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, mix with silica gel, and purify the crude product by silica gel column chromatography with petroleum ether / ethyl acetate (V / V) = 40 / 1–20 / 1 to obtain tBu-iPr-Cl-2, 11.00 g white solid, yield 81%. 1H NMR(500MHz,DMSO)δ(ppm):1.10(d,J=7.0Hz,6H),1.12(d,J=7.0Hz,6H),1.30(s,9H),1.33(s,9H),2.70–2.78(m,2H),6.79(t,J=2.0Hz,1H),7.05(t,J=2.0Hz,1H),7.07(dd,J=8.5,2.0Hz,1H),7.09(t,J=1.5Hz,1H),7.16(dd,J=8.0,1.5Hz,1H),7.24(s,1H),7.27(d,J=3.0Hz,1H),7.28(dd,J=5.5,2.0Hz,1H),7.39(t,J=8.0Hz,1H),7.52(d,J=2.0Hz,1H),7.523(d,J=0.5Hz,1H),7.56(d,J=1.5Hz,1H),8.12(d,J=3.0Hz,1H),8.14(d,J=2.0Hz,1H),8.55(d,J=5.0Hz,1H).

[0112]

[0113] Synthesis of ligand L26: tBu-iPr-Cl-1 (6.36 g, 9.87 mmol, 1.0 equiv), tBu-Ph-NH2 (3.75 g, 11.84 mmol, 1.2 equiv), tris(dibenzylacetone)dipalladium (275 mg, 0.30 mmol, 0.03 equiv), 2-(dicyclohexylphosphine)-3,6-dimethoxy-2,4,6-tri-1-propyl-11-biphenyl (242 mg, 0.59 mmol, 0.06 equiv), and sodium tert-butoxide (1.90 g, 19.74 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, toluene (80 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 80 °C, and stirred for 4 hours. TCL TLC monitoring showed the reaction was essentially complete. After cooling to room temperature, deionized water and ethyl acetate (100 mL) were added for extraction, repeated twice. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, and mixed with silica gel. The crude product was purified by silica gel column chromatography with petroleum ether / ethyl acetate (V / V) = 60 / 1–40 / 1 to give an intermediate diamine compound, 8.00 g of green solid, yield 76%. Since this intermediate diamine compound is unstable, it was used directly in subsequent reactions. The intermediate diamine compound (9.40 g, 10.2 mmol, 1.0 equiv) and ammonium hexafluorophosphonate (3.32 g, 20.4 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, triethyl orthoformate (30 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 75 °C, and stirred for half an hour. TCL TLC monitoring showed the reaction was essentially complete. The solvent was removed by vacuum concentration, and the sample was mixed with silica gel. The crude product was then purified by silica gel column chromatography with dichloromethane / methanol (V / V) = 200 / 1 as eluent, yielding L26, a purple solid, 9.00 g, with a yield of 82%. 1H NMR(500MHz, CDCl3)δ(ppm):1.09(d,J=7.0Hz,6H),1.12(d,J=7.0Hz,6H),1.33(s,9H),1.42(s,9H),1.43(s,9H),2.70–2.78(m,2H ),6.61(t,J=2.0Hz,1H),6.95–6.98(m,2H),7.02–7.09(m,4H),7.15(t,J=2.0Hz,1H),7.26(s,1H),7.27–7.29(m,2H),7.35–7.36(m 2H),7.40(t,J=8.0Hz,1H),7.58(d,J=2.5Hz,1H),7.61(d,J=2.0Hz,1H),7.63–7.66(m,4H),7.69(d,J=1.0Hz,1H),7.71(dd,J=8.5,2.0 Hz,1H),7.82(d,J=8.0Hz,1H),7.85(d,J=8.5Hz,1H),7.92(d,J=1.5Hz,1H),8.11(d,J=8.5Hz,1H),8.59(s,1H),8.62(d,J=5.0Hz,1H).

[0114] Synthesis of metallized Pt26: L26 (6.28 g, 5.82 mmol, 1.0 equiv), (1,5-cyclooctadiene)platinum(II) chloride (2.12 g, 6.11 mmol, 1.05 equiv), and sodium acetate (1.43 g, 17.46 mmol, 3.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, N,N-dimethylformamide (96 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 150 °C, and stirred in the dark for one day, then cooled to room temperature. The solvent was removed by vacuum distillation. The crude product was purified by silica gel column chromatography with petroleum ether / dichloromethane (V / V) = 1 / 1 to give Pt26, 5.00 g of yellow solid, yield 76%.

[0115] 1H NMR (500MHz, CDCl3) δ (ppm): 1.08–1.19 (m, 12H), 1.19 (s, 9H), 1.36 (s, 9H), 1.50 (s, 9H), 2.75 (hept, J = 7.0Hz, 1H), 2.86 (hept, J=7.0Hz,1H),6.26(dd,J=6.5,2.0Hz,1H),6.83(s,1H),7.01(s,1H),7.20(dd,J=8.5Hz,1H),7.22(s,1H),6.73–7.24(br,3H),7 .27–7.30(m,3H),7.41(t,J=3.0Hz,2H),7.26–7.53(br,3H),7.59(s,1H),7.66(d,J=0.5Hz,1H),7.75(d,J=8.5Hz,1H),7.80(d, J=8.0Hz,1H),7.84(d,J=9.0Hz,1H),7.85(d,J=1.5Hz,1H),7.95(d,J=2.0Hz,1H),8.05(d,J=8.0Hz,1H),9.00(d,J=5.5Hz,1H).

[0116] Example 3: The synthesis route of the tetradentate ring platinum(II) complex phosphorescent material Pt529 is as follows:

[0117]

[0118] Synthesis of ligand L529: iPr-Cl-2 (9.74 g, 16.59 mmol, 1.0 equiv), tBu-Ph-NH2 (6.30 g, 19.91 mmol, 1.2 equiv), tris(dibenzylacetone)dipalladium (156 mg, 0.17 mmol, 0.03 equiv), 2-(dicyclohexylphosphine)-3,6-dimethoxy-2,4,6-tri-1-propyl-11-biphenyl (354 mg, 0.66 mmol, 0.04 equiv), and sodium tert-butoxide (3.19 g, 33.18 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, toluene (50 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 110 °C, and stirred for 4 hours. The reaction was then monitored by TCL (Temporary Chromatography-Based Logging) to indicate that the reaction was essentially complete. After cooling to room temperature, deionized water and ethyl acetate (100 mL) were added for extraction, repeated twice. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, and mixed with silica gel. The crude product was purified by silica gel column chromatography with petroleum ether / ethyl acetate (V / V) = 60 / 1-40 / 1, yielding an intermediate diamine compound, a blue solid of 13.38 g, with a yield of 93%. Since this intermediate diamine compound was unstable, it was used directly in subsequent reactions. The intermediate diamine compound (13.38 g, 15.43 mmol, 1.0 equiv) and ammonium hexafluorophosphonate (5.03 g, 30.86 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, triethyl orthoformate (20 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 80 °C, and stirred for half an hour. TCL TLC monitoring showed the reaction was essentially complete. The solvent was removed by vacuum concentration, and the sample was mixed with silica gel. The crude product was then purified by silica gel column chromatography with dichloromethane / methanol (V / V) = 200 / 1 as eluent to obtain L529, a pink solid of 15.11 g, with a yield of 95%. 1H NMR (500MHz, DMSO) δ (ppm): 0.99 (d, J = 7.0Hz, 6H), 1.03 (d, J = 7.0Hz, 6H), 1.22 (s, 9H), 1.42 (s, 9H), 2 .54–2.63(m,2H),7.13–7.14(m,2H),7.16–7.21(m,4H),7.23–7.27(m,3H),7.33(t,J=8.0Hz,1H),7. 41–7.48(m,5H),7.52–7.56(m,3H),7.60–7.64(m,2H),7.70(d,J=2.5Hz,1H),7.77(t,J=8.0Hz,1H), 7.81–7.87(m,3H),8.32(d,J=8.0Hz,1H),8.38(d,J=8.5Hz,1H),8.54(d,J=5.0Hz,1H),10.44(s,1H).

[0119] Synthesis of metallized Pt529: L529 (10.82 g, 10.58 mmol, 1.0 equiv), (1,5-cyclooctadiene)platinum(II) chloride (3.86 g, 11.11 mmol, 1.05 equiv), and sodium acetate (2.60 g, 31.74 mmol, 3.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, N,N-dimethylformamide (125 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 150 °C, and stirred in the dark for one day, then cooled to room temperature. The solvent was removed by vacuum distillation. The crude product was purified by silica gel column chromatography with petroleum ether / dichloromethane (V / V) = 1 / 1 to give Pt529, 5.80 g of yellow solid, yield 51%. 1 H NMR(500MHz, CDCl3)δ(ppm):1.07(s,9H),1.09–1.21(br,12H),1.24(s,9H),2.72(br,1H),2.92 (br,1H),6.22(dd,J=6.5,2.0Hz,1H),7.17(d,J=7.0Hz,2H),6.37–7.30(br,6H),7.28(d,J=8.0H z,2H),7.33(t,J=7.5Hz,1H),7.42(t,J=7.5Hz,2H),7.58–7.60(m,2H),7.26–7.72(br,5H),7.7 8(d,J=5.0Hz,1H),7.84–7.86(m,2H),7.09(d,J=7.5Hz,1H),8.10(d,J=8.0Hz,1H),8.93(s,1H).

[0120] Example 4: The synthesis route of the tetradentate ring platinum(II) complex phosphorescent material Pt530 is as follows:

[0121]

[0122] Synthesis of ligand L530: tBu-iPr-Cl-2 (7.64 g, 11.88 mmol, 1.0 equiv), tBu-Ph-NH2 (4.51 g, 14.26 mmol, 1.2 equiv), tris(dibenzylacetone)palladium (330 mg, 0.36 mmol, 0.03 equiv), 2-dicyclohexylphosphine-2,4,6-triisopropylbiphenyl (338 mg, 0.71 mmol, 0.06 equiv), and sodium tert-butoxide (2.28 g, 23.76 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, toluene (60 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 110 °C, and stirred for 6 hours. TCL TLC monitoring showed the reaction was essentially complete. Cool to room temperature, extract with deionized water and ethyl acetate (100 mL), repeat twice, combine organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, mix with silica gel, and purify the crude product by silica gel column chromatography with eluent: petroleum ether / ethyl acetate (V / V) = 60 / 1–40 / 1, to obtain an intermediate diamine compound, 8.00 g of blue solid, yield 73%. Since this intermediate diamine compound is unstable, it was used directly in subsequent reactions. Add the intermediate diamine compound (8.00 g, 8.66 mmol, 1.0 equiv) and ammonium hexafluorophosphonate (2.82 g, 17.32 mmol, 2.0 equiv) to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, inject triethyl orthoformate (40 mL) under nitrogen protection. Place the reaction mixture in an oil bath, heat to 80 °C and stir for half an hour. TCL TLC monitoring showed the reaction was essentially complete. The solvent was removed by vacuum concentration, and the sample was mixed with silica gel. The crude product was then purified by silica gel column chromatography with dichloromethane / methanol (V / V) = 200 / 1 as eluent to obtain L530, a white solid of 8.28 g, with a yield of 89%. 1H NMR(500MHz,DMSO)δ(ppm):0.98(d,J=6.5Hz,6H),1.02(d,J=7.0Hz,6H),1.19(s,9H),1.33(s,9H),1.41(s,9H), 2.55–2.63(m,2H),7.10–7.16(m,3H),7.18(d,J=7.5Hz,3H),7.24–7.26(m,4H),7.31(t,J=8.0Hz,1H),7.42(dd,J =5.5,1.5Hz,1H),7.44–7.48(m,4H),7.53(d,J=8.0Hz,1H),7.56(d,J=2.0Hz,1H),7.60–7.63(m,2H),7.71(d,J= 2.0Hz,1H),7.80–7.89(m,3H),8.31(d,J=8.0Hz,1H),8.37(d,J=8.5Hz,1H),8.53(d,J=5.5Hz,1H),10.43(s,1H).

[0123] Synthesis of metallized Pt530: L530 (8.28 g, 7.67 mmol, 1.0 equiv), (1,5-cyclooctadiene)platinum(II) chloride (2.79 g, 8.05 mmol, 1.05 equiv), and sodium acetate (1.89 g, 23.01 mmol, 3.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, diethylene glycol dimethyl ether (127 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 150 °C, and stirred in the dark for one day, then cooled to room temperature. The solvent was removed by vacuum distillation. The crude product was purified by silica gel column chromatography with petroleum ether / dichloromethane (V / V) = 1 / 1 to give Pt530, a yellow solid, 5.00 g, yield 57%. 1H NMR(500MHz, CDCl3)δ(ppm):1.07(s,9H),1.08–1.21(br,12H),1.25(s,9H),1.50(s,9H),2.70–2.95( m,2H),6.21(dd,J=6.0,1.5Hz,1H),7.15–7.16(m,1H),7.21(s,1H),6.74–7.24(br,5H),7.27–7.29(m ,2H),7.42(t,J=8.0Hz,2H),7.59(s,1H),7.64(s,1H),7.27–7.66(br,5H),7.78(d,J=5.5Hz,1H),7.8 46(d,J=2.0Hz,1H),7.847(d,J=8.0Hz,1H),8.07(d,J=8.0Hz,1H),8.09(d,J=7.5Hz,1H),8.93(s,1H).

[0124] Example 5: The synthesis route of the tetradentate ring platinum(II) complex phosphorescent material Pt121 is as follows:

[0125]

[0126] Synthesis of intermediate mtBu-NO2: o-Bromonitrobenzene (18.46 g, 91.37 mmol, 1.0 equiv), 3-tert-butylaniline (15.00 g, 100.51 mmol, 1.1 equiv), tris(dibenzylacetone)dipalladium (833 mg, 0.91 mmol, 0.01 equiv), 2-dicyclohexylphosphine-2,6-dimethoxybiphenyl (1.50 g, 3.65 mmol, 0.04 equiv), and cesium carbonate (37.21 g, 114.21 mmol, 1.25 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, toluene (150 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 110 °C, and stirred for 12 hours. TCL TLC monitoring showed the reaction was essentially complete. Cool to room temperature, add deionized water and ethyl acetate (100 mL) for extraction, repeat twice, combine organic phases, dry with anhydrous sodium sulfate, concentrate under reduced pressure to remove solvent, mix with silica gel, and purify the crude product by silica gel column chromatography with petroleum ether-petroleum ether / ethyl acetate (V / V) = 40 / 1 to obtain mtBu-NO2, 20.95 g of red solid, yield 86%.

[0127] Synthesis of intermediate mtBu-NH2: mtBu-NO2 (20.95 g, 77.50 mmol, 1.0 equiv) and palladium on carbon (329 mg, 3.10 mmol, 0.04 equiv) were added to a dry round-bottom flask equipped with a magnetically stirred rotor. After purging the flask three times with an oil pump, ethanol (250 mL) and ethyl acetate (200 mL) were injected under hydrogen protection. The reaction mixture was placed in an oil bath under a hydrogen atmosphere and heated to 40 °C with stirring for two days. The reaction was monitored by TCL spotting to indicate near-complete reaction. After cooling to room temperature, ethyl acetate (100 mL) was added for extraction, repeated twice. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, and mixed with silica gel. The crude product was purified by silica gel column chromatography with petroleum ether / ethyl acetate (V / V) = 10 / 1, yielding mtBu-NH2, a brown solid, 16.74 g, yield 90%.

[0128]

[0129] Synthesis of ligand L121: iPr-Cl-1 (5.00 g, 8.50 mmol, 1.0 equiv), mBu-Ph-NH2 (2.25 g, 9.35 mmol, 1.1 equiv), tris(dibenzylacetone)dipalladium (238 mg, 0.26 mmol, 0.03 equiv), 2-(dicyclohexylphosphine)-3,6-dimethoxy-2,4,6-tri-1-propyl-11-biphenyl (243 mg, 0.51 mmol, 0.06 equiv), and sodium tert-butoxide (1.63 g, 17.00 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, toluene (50 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 110 °C, and stirred for 5 hours. The reaction was then monitored by TCL (Temporary Chromatography-Based Logging) to indicate that the reaction was essentially complete. The mixture was cooled to room temperature, extracted with deionized water and ethyl acetate (100 mL), and the extraction was repeated twice. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, and mixed with silica gel. The crude product was purified by silica gel column chromatography with petroleum ether / ethyl acetate (V / V) = 60 / 1–40 / 1 to give an intermediate diamine compound, 6.25 g of white solid, yield 93%. Since this intermediate diamine compound was unstable, it was used directly in subsequent reactions. The intermediate diamine compound (6.25 g, 7.90 mmol, 1.0 equiv) and ammonium hexafluorophosphonate (2.58 g, 15.80 mmol, 2.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, triethyl orthoformate (100 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 70 °C, and stirred for half an hour. TCL TLC monitoring showed the reaction was essentially complete. The solvent was removed by vacuum concentration, and the sample was mixed with silica gel. The crude product was then purified by silica gel column chromatography with dichloromethane / methanol (V / V) = 200 / 1 as eluent to obtain L121, a purple solid weighing 6.58 g, with a yield of 88%. 1H NMR (500MHz, DMSO) δ (ppm): 1.03 (d, J = 7.0Hz, 6H), 1.06 (d, J = 7.0Hz, 6H), 1.33 (s, 9H), 1.36 (s, 9H), 2.60 (hept, 2H), 7.18 (dd, J = 8.5, 2. 0Hz,1H),7.23(dd,J=8.5,1.5Hz,1H),7.24(d,J=8.0Hz,2H),7.36(t,J=8.0Hz,1H),7.46(ddd,J=9.0,2.5,1.0Hz,1H),7.50(dd,J=5.5,1 .5Hz,1H),7.52(d,J=2.5Hz,1H),7.59(t,J=2.0Hz,1H),7.67(ddd,J=9.0,2.0,1.0Hz,1H),7.69–7.71(m,2H),7.75–7.78(m,4H),7.80(d ,J=1.0Hz,1H),7.81–7.84(m,2H),7.89–7.95(m,2H),8.07(d,J=1.0Hz,1H),8.37(d,J=8.5Hz,1H),8.61(d,J=5.5Hz,1H),10.51(s,1H).

[0130] Synthesis of metallized Pt121: L121 (5.81 g, 6.13 mmol, 1.0 equiv), (1,5-cyclooctadiene)platinum(II) chloride (2.23 g, 6.44 mmol, 1.05 equiv), and sodium acetate (1.51 g, 18.39 mmol, 3.0 equiv) were added to a dry round-bottom flask equipped with a magnetic stirrer. After purging with nitrogen three times using an oil pump, diethylene glycol dimethyl ether (115 mL) was injected under nitrogen protection. The reaction mixture was placed in an oil bath, heated to 150 °C, and stirred in the dark for one day, then cooled to room temperature. The solvent was removed by vacuum distillation. The crude product was purified by silica gel column chromatography using petroleum ether / dichloromethane / ethyl acetate (V / V / V) = 10 / 1 / 0.2-8 / 1 / 0.2, yielding Pt121, a yellow solid, 4.70 g, in 77% yield. 1H NMR (500MHz, CDCl3) δ (ppm): 1.01 (s, 9H), 1.02–1.45 (br, 21H), 2.74 (br, 2H), 5.75 (d, J = 6.0Hz, 1H), 7.10 (d, J =8.5Hz,1H),7.13(d,J=8.0Hz,1H),7.21(t,J=8.0Hz,1H),7.24–7.25(m,2H),7.27(s,1H),7.34–7.37(m,2H),7 .39(t,J=7.5Hz,1H),7.45(d,J=8.0Hz,1H),7.42–7.46(m,1H),7.49(td,J=6.5,2.5Hz,2H),7.52(d,J=6.5Hz,1 H),7.32–7.56(br,1H),7.67(d,J=1.5Hz,2H),7.75–7.83(m,3H),8.14(d,J=8.0Hz,1H),8.68(d,J=6.0Hz,1H).

[0131] Example 6: Synthesis of Pt27

[0132] Pt27 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product L27 was obtained, a white solid, 703 mg, in 78% yield. Molecular weight [M] + :1037.6. The target product Pt27 was synthesized, yielding 200 mg of a yellow solid, in a yield of 40%. Molecular weight [M+H] + :1230.6.

[0133] Example 7: Synthesis of Pt33

[0134] Pt33 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product L33 was obtained, a light green, foamy solid, 600 mg in yield (80%). Molecular weight [M] + :949.5. The target product Pt33 was synthesized, a yellow solid, 250 mg, in yield of 45%. Molecular weight [M+H] + :1142.5.

[0135] Example 8: Synthesis of Pt73

[0136] Pt73 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product L73 was obtained as a white solid (500 mg), in 88% yield. Molecular weight [M] + :1177.7. The target product Pt73 was synthesized, a yellow solid, 150 mg, yield 38%. Molecular weight [M+H] + :1370.7.

[0137] Example 9: Synthesis of Pt74

[0138] Pt74 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product L74 was obtained as a white solid (700 mg), in 89% yield. Molecular weight [M] + :1233.8. The target product Pt74 was synthesized, a yellow solid, 380 mg, in yield of 56%. Molecular weight [M+H] + :1426.8.

[0139] Example 10: Synthesis of Pt75

[0140] Pt75 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product L75 was obtained, a white solid, 530 mg, in 80% yield. Molecular weight [M] + 1337.9. The target product Pt75 was synthesized, a yellow solid, 158 mg, in yield of 38%. Molecular weight [M+H] + :1530.8.

[0141] Example 11: Synthesis of Pt81

[0142] Pt81 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product L81 was obtained, a white solid, 624 mg, in yield of 67%. Molecular weight [M] + :1249.8. The target product Pt81 was synthesized, a yellow solid, 109 mg, yield 38%. Molecular weight [M+H] + :1442.7.

[0143] Example 12: Synthesis of Pt152

[0144] Pt152 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 88 mg, in yield of 25%. Molecular weight [M+H] + :1215.5.

[0145] Example 13: Synthesis of Pt159

[0146] Pt159 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 113 mg, in 29% yield. Molecular weight [M+H] + :1075.5.

[0147] Example 14: Synthesis of Pt182

[0148] Pt182 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 205 mg, in yield of 22%. Molecular weight [M+H] + :1006.3.

[0149] Example 15: Synthesis of Pt194

[0150] Pt194 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 306 mg, in 24% yield. Molecular weight [M+H] + :1112.5.

[0151] Example 16: Synthesis of Pt214

[0152] Pt214 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 105 mg, in 31% yield. Molecular weight [M+H] + :1188.5.

[0153] Example 17: Synthesis of Pt217

[0154] Pt217 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product L217 was obtained as a white solid (310 mg), in 72% yield. Molecular weight [M] + 897.5. The target product, Pt217, was synthesized as a yellow solid, 123 mg, in 61% yield. Molecular weight [M+H] + :1090.4.

[0155] Example 18: Synthesis of Pt219

[0156] Pt219 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product L219 was obtained, a white solid, 433 mg, in 65% yield. Molecular weight [M] + 965.5. The target product Pt219 was synthesized, a yellow solid, 99 mg, in yield of 33%. Molecular weight [M+H] + :1158.5.

[0157] Example 19: Synthesis of Pt225

[0158] Pt225 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product L225 was obtained, a white solid, 430 mg, in 64% yield. Molecular weight [M] + :969.5. The target product Pt225 was synthesized, a yellow solid, 100 mg, in yield of 32%. Molecular weight [M+H] + :1162.4.

[0159] Example 20: Synthesis of Pt250

[0160] Pt250 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product L250 was obtained, a white solid, 433 mg, in yield of 71%. Molecular weight [M] + :1138.7. The target product Pt250 was synthesized, a yellow solid, 110 mg, in yield of 32%. Molecular weight [M+H] + :1331.7.

[0161] Example 21: Synthesis of Pt256

[0162] Pt256 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product L256 was obtained, a light green, foamy solid, 430 mg in yield (77%). Molecular weight [M] + 1255.8. The target product Pt256 was synthesized, a yellow solid, 188 mg, in yield of 44%. Molecular weight [M+H] + :1448.8.

[0163] Example 22: Synthesis of Pt263

[0164] Pt263 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 220 mg, in yield of 45%. Molecular weight [M+H] + :1460.8.

[0165] Example 23: Synthesis of Pt264

[0166] Pt264 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 120 mg, in yield of 23%. Molecular weight [M+H] + :1497.8.

[0167] Example 24: Synthesis of Pt272

[0168] Pt272 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 122 mg, in 35% yield. Molecular weight [M+H] + :1116.4.

[0169] Example 25: Synthesis of Pt300

[0170] Pt300 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 159 mg, in yield of 43%. Molecular weight [M+H] + :1059.5.

[0171] Example 26: Synthesis of Pt3O5

[0172] Pt305 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 245 mg, in 30% yield. Molecular weight [M+H] + :1075.5.

[0173] Example 27: Synthesis of Pt311

[0174] Pt311 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 180 mg, in 35% yield. Molecular weight [M+H] + :1140.5.

[0175] Example 28: Synthesis of Pt312

[0176] Pt312 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 101 mg, in yield of 29%. Molecular weight [M+H] + :1177.6.

[0177] Example 29: Synthesis of Pt418

[0178] Pt418 was synthesized following the same synthetic steps and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 98 mg, in yield of 23%. Molecular weight [M+H] + :1129.5.

[0179] Example 30: Synthesis of Pt419

[0180] Pt419 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 86 mg, in yield of 26%. Molecular weight [M+H] + :1480.6.

[0181] Example 31: Synthesis of Pt420

[0182] Pt420 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 57 mg, in yield of 29%. Molecular weight [M+H] + :1398.7.

[0183] Example 32: Synthesis of Pt423

[0184] Pt423 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 69 mg, in 32% yield. Molecular weight [M+H] + :1297.6.

[0185] Example 33: Synthesis of Pt425

[0186] Pt425 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 106 mg, in yield of 31%. Molecular weight [M+H] + :1212.6.

[0187] Example 34: Synthesis of Pt432

[0188] Pt432 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 70 mg, in 33% yield. Molecular weight [M+H] + :1394.7.

[0189] Example 35: Synthesis of Pt445

[0190] Pt445 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 123 mg, in yield of 22%. Molecular weight [M+H] + :1416.6.

[0191] Example 36: Synthesis of Pt448

[0192] Pt448 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 69 mg, in 26% yield. Molecular weight [M+H] + :1506.7.

[0193] Example 37: Synthesis of Pt477

[0194] Pt477 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 150 mg, in 38% yield. Molecular weight [M+H] + :1436.6.

[0195] Example 38: Synthesis of Pt515

[0196] Pt515 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 227 mg, in yield of 36%. Molecular weight [M+H] + :1127.5.

[0197] Example 39: Synthesis of Pt523

[0198] Pt523 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 316 mg, in yield of 27%. Molecular weight [M+H] +:1024.4.

[0199] Example 40: Synthesis of Pt524

[0200] Pt524 was synthesized following the same synthetic steps and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 132 mg, in 25% yield. Molecular weight [M+H] + :1189.5.

[0201] Example 41: Synthesis of Pt549

[0202] Pt549 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 78 mg, in 29% yield. Molecular weight [M+H] + :1103.5.

[0203] Example 42: Synthesis of Pt550

[0204] Pt550 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 54 mg, in yield of 33%. Molecular weight [M+H] + :1300.6.

[0205] Example 43: Synthesis of Pt552

[0206] Pt552 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 77 mg, in yield of 26%. Molecular weight [M+H] + :1251.5.

[0207] Example 44: Synthesis of Pt557

[0208] Pt557 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 64 mg, in yield of 23%. Molecular weight [M+H] + :1228.5.

[0209] Example 45: Synthesis of Pt568

[0210] Pt568 was synthesized following the same synthetic steps and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 69 mg, in 28% yield. Molecular weight [M+H] + :1280.6.

[0211] Example 46: Synthesis of Pt618

[0212] Pt618 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 62 mg, in yield of 31%. Molecular weight [M+H]+ :1536.8.

[0213] Example 47: Synthesis of Pt911

[0214] Pt911 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 49 mg, in 25% yield. Molecular weight [M+H] + :1353.7.

[0215] Example 48: Synthesis of Pt937

[0216] Pt937 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 125 mg, in yield of 27%. Molecular weight [M+H] + :1146.5.

[0217] Example 49: Synthesis of Pt940

[0218] Pt940 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 138 mg, in 40% yield. Molecular weight [M+H] + :1326.6.

[0219] Example 50: Synthesis of Pt945

[0220] Pt945 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 158 mg, in yield of 39%. Molecular weight [M+H] + :1326.6.

[0221] Example 51: Synthesis of Pt955

[0222] Pt955 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 47 mg, in 36% yield. Molecular weight [M+H] + :1598.8.

[0223] Example 52: Synthesis of Pt969

[0224] Pt969 was synthesized following the same synthetic procedures and reaction conditions as compound Pt25. The target product was obtained as a yellow solid, 138 mg, in yield (33%). Molecular weight [M+H] + :1230.6.

[0225] Theoretical calculation explanation

[0226] The geometry of the ground-state (S0) molecule was optimized using density functional theory (DFT). DFT calculations were performed using the B3LYP functional, with the C, H, O, and N atoms using the 6-31G(d) basis set and the Pt atom using the LANL2DZ basis set.

[0227] Table 1. HOMO and LUMO of some metal complexes of the present invention

[0228]

[0229]

[0230] Based on the calculation data above, it can be seen that introducing steric hindrance groups, such as 2,6-diisopropylphenyl, at different positions of carbazole inhibits intermolecular interactions, resulting in a lower emission shoulder peak, a narrower half-width, and higher color purity, which can meet the requirements of blue light materials.

[0231] Photophysical properties:

[0232] Figure 1 This is the room temperature emission spectrum of platinum complexes BD-02 and Pt25 in dichloromethane solution; Figure 2 This is the room temperature emission spectrum of platinum complexes BD-02 and Pt26 in dichloromethane solution; Figure 3 This is the room temperature emission spectrum of platinum complexes BD-02 and Pt529 in dichloromethane solution; Figure 4 This is the room temperature emission spectrum of platinum complexes BD-02 and Pt530 in dichloromethane solution; Figure 5 It is platinum complex BD-02 and

[0233] Room temperature emission spectrum of Pt121 in dichloromethane solution; Figure 6 Table 1 shows a comparison of the emission spectra of platinum complex BD-02 and Pt complexes Pt25, Pt26, Pt529, Pt530, and Pt121 in dichloromethane. Table 2 presents the photophysical properties of some of the platinum(II) complexes of this invention in dichloromethane solution at room temperature.

[0234] Table 2. Photophysical properties of some platinum(II) complexes in dichloromethane solution

[0235] coordination compounds Maximum emission wavelength Half peak width Pt25 455.8nm 18.8nm Pt26 460.5nm 23.0nm Pt121 457.4nm 22.6nm Pt529 457.8nm 19.0nm Pt530 460.9nm 21.8nm

[0236] By comparing the room temperature emission spectra of the platinum complex in dichloromethane solution, it was found that introducing sterically hindered groups at different positions of carbazole suppressed intermolecular interactions, resulting in a lower emission shoulder, narrower half-peak width, and higher color purity.

[0237] Manufacturing of OLED devices:

[0238] As a reference fabrication method for a device embodiment, the present invention involves depositing a p-doped material onto the surface or anode of an ITO glass with a light-emitting area of ​​2 mm × 2 mm, or co-evaporating this p-doped material with a hole injection material at a concentration of 1% to 50% to form a 5-100 nm hole injection layer (HIL) and a 5-200 nm hole transport layer (HTL). Subsequently, a 10-100 nm light-emitting layer (EML) (which may contain the compound described in this invention) is formed on the hole transport layer, followed by a 20-200 nm electron transport layer (ETL) and a 50-200 nm cathode. If necessary, an electron blocking layer (EBL) is added between the HTL and EML layers, and an electron injection layer (EIL) is added between the ETL and the cathode, thereby fabricating an OLED device. The OLED is then tested using standard methods. Unless otherwise specified, the device materials involved in this invention can be obtained by known synthesis methods.

[0239] In a preferred embodiment, the structure of the device Example 1 provided by the present invention is: ITO / P-4 (10nm) / NPD (60nm) / HT-85 (5nm) / platinum (II) complex:HT-85:ET-45 (Pt25:HT-85:ET-45 mass ratio is 10:60:30, 25nm) / ET-14 (45nm) / LiQ (1nm) / Al (100nm).

[0240] Device Examples 2-38 and Comparative Example 1 were fabricated using structures similar to those in Device Example 1, the only difference being that the Pt25 in Device Example 1 was replaced with the platinum(II) complex shown in Table 3. The luminescence properties of the comparative examples and each device example were tested using standard methods, and the data are shown in Table 3. The device structures involved are as follows:

[0241]

[0242] Table 3. Device Light Emitting Characteristics Data Table

[0243]

[0244]

[0245] As shown in Table 3, compared with Comparative Example 1, Device Examples 1-38 prepared in this application exhibit excellent device performance in terms of driving voltage, current efficiency, and device lifetime; in addition, the color purity of the devices is also greatly improved. The performance improvement of each device example is based on the fact that the specific compound material of this invention has a small emission shoulder and better electron transport capability. It can be seen that using it as a light-emitting layer material to prepare electronic devices can reduce the driving voltage while achieving higher current efficiency, device lifetime, and color purity. This indicates that the compound provided by this invention has certain commercial application value. Furthermore, the devices prepared by this invention are all deep blue light devices, and the CIEy values ​​are all less than 0.19.

[0246] In a preferred embodiment, the structure of device example 39 provided by the present invention is as follows: ITO / P-4 (10nm) / NPD (60nm) / HT-85 (5nm) / platinum (II) complex: boron-containing compound: HT-85:ETH-45 (Pt25:BN1-8:HT-85:ET-45 mass ratio is 10:1:59:30, 25nm) / ET-14 (45nm) / LiQ (1nm) / Al (100nm).

[0247] Device Examples 40-45 were fabricated using a structure similar to that of Device Example 39, the only difference being that the platinum(II) complex and boron-containing compound in Device Example 39 were replaced with platinum(II) complexes listed in Table 4. The structural formulas of the devices involved are as follows, and the device structure and luminescence characteristic data are shown in Table 4.

[0248]

[0249] Table 4. Device Structure and Luminescent Properties Data

[0250]

[0251] As shown in Table 4, when the compounds of this invention are used as sensitizing materials, together with boron-containing compounds as luminescent materials in devices, the performance of each device is significantly improved. This further demonstrates that the compounds provided by this invention have certain commercial application value. Adding boron-containing compounds to sensitize the device structure can further reduce the CIEy value, thereby improving the purity of the emitted color.

[0252] The above description is only a preferred embodiment of the present invention, but the scope of protection of the present invention is not limited thereto. Any equivalent substitutions or modifications made by those skilled in the art within the scope of the technology disclosed in the present invention, based on the technical solution and inventive concept of the present invention, should be covered within the scope of protection of the present invention.

Claims

1. A tetradentate cyclometalated platinum (II) complex characterized in that, The complex has a structure as shown in formula (I): In formula (I), R 1 - R 6 each independently represents no substitution, mono-substitution, di-substitution, tri-substitution, tetra-substitution, or the maximum number of substitutions; R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are each independently selected from one or more of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted C1–C30alkyl, substituted or unsubstituted C3–C30cycloalkyl, substituted or unsubstituted C3–C30heterocycloalkyl, C1–C30alkoxy, substituted or unsubstituted C6–C60aryl, substituted or unsubstituted C5–C60heteroaryl, substituted or unsubstituted C6–C60aryloxy, mono- or di(C1–C30alkyl)amino, mono- or di(substituted or unsubstituted C6–C60aryl)amino, C1–C30alkylsilyl, C6–C60arylsilyl; when containing substitution, the substitution is each independently selected from one or more of hydrogen, deuterium, halogen, C1–C30alkyl, C3–C30cycloalkyl, C6–C60aryl, C5–C60heteroaryl.

2. The tetradentate cyclometalated platinum (II) complex of claim 1, wherein The R 1 R 2 R 3 R 4 R 5 and R 6 Each is independently selected from hydrogen, deuterium, CD3, F, CF3, CN, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isonyl, sec-nonyl, tert-nonyl. One or more of the following: cyclobutyl, cyclopentyl, cyclohexyl, adamantyl, phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, tetrahydronaphthyl, tert-butylphenyl, pyridyl, quinolinyl, dimethylfluorenyl, carbazole, dibenzofuranyl, dibenzothiophene, trimethylsilyl, triarylsilyl, methoxy, phenothiazinyl, phenotoxazinyl, dimethylacridyl, N-phenylcarbazole, and diarylamino.

3. The tetradentate cyclometallated platinum (II) complex of claim 1, wherein The complex is selected from any one of the chemical structures shown below, wherein "D" represents deuterium:

4. Use of the tetradentate cyclometalated platinum (II) complex according to any one of claims 1 to 3 for the preparation of an electronic device, which comprises one or more of an organic electroluminescent device, an organic integrated circuit, an organic field-effect transistor, an organic thin-film transistor, an organic light-emitting transistor, an organic solar cell, an organic optical detector, an organic photoreceptor, an organic field-quench device, a light-emitting electrochemical cell, or an organic laser diode.

5. An organic electroluminescent device, characterized by comprising The organic electroluminescent device comprises a cathode, an anode, and an organic functional layer interposed therebetween; the organic functional layer comprises a light-emitting layer, and the light-emitting layer comprises the tetradentate cyclometalated platinum (II) complex according to any one of claims 1 to 3.

6. The organic electroluminescent device according to claim 5, characterized in that The light-emitting layer further comprises a fluorescent dopant material, and the fluorescent dopant material is a boron-containing compound.

7. An organic optoelectronic device, characterized in that The organic optoelectronic device comprises a substrate layer; a first electrode on the substrate; an organic light-emitting functional layer on the first electrode; and a second electrode on the organic light-emitting functional layer; wherein the organic light-emitting functional layer comprises the tetradentate cyclometalated platinum (II) complex according to any one of claims 1 to 3.

8. A composition characterized in that, The composition comprises the tetradentate cyclometalated platinum (II) complex according to any one of claims 1 to 3.

9. A formulation characterized in that, The preparation comprises the tetradentate cyclometalated platinum (II) complex according to any one of claims 1 to 3.

10. A display or illumination device, characterized in that The device comprises one or more of the organic electroluminescent device according to claim 5 or the organic optoelectronic device according to claim 7.

Images