Circularly polarized luminescent material and use thereof, luminescent display component and display device

Abstract

The present invention discloses circularly polarized luminescent materials and uses of spirochiral tetradentate cyclometallated platinum(II) and palladium(II) complexes based on phenyl-benzimidazole and its derivatives. The spirochiral metal complex molecules have a central chiral segment L of the tetradentate ligand. a As a result, the entire tetradentate ligand can be coordinated to the metal ion in a manner with little steric hindrance, spontaneously inducing the formation of an optically pure spiro-chiral metal complex circularly polarized luminescent material. Such spiro-chiral metal complex circularly polarized luminescent material does not require chiral resolution and has high chemical and thermal stability, and is therefore of important use in circularly polarized light-emitting devices.

Description

[Technical Field]

[0001] The present invention relates to circularly polarized luminescent materials and uses thereof, in particular to central chirality-induced spiro-chirality tetradentate cyclometalated platinum(II) and palladium(II) complex circularly polarized luminescent materials and uses thereof based on phenyl-benzimidazole and its derivatives. [Background technology]

[0002] Circularly polarized luminescence (CPL) is a phenomenon in which chiral luminescent materials emit left-handed or right-handed circularly polarized light after excitation, so the design and evolution of chiral luminescent materials is important in this field. Through advanced research by researchers, circularly polarized luminescent materials have been found to have important applications in fields such as 3D display, data storage, quantum computing, optical anti-counterfeiting, bioimaging, and asymmetric synthesis.

[0003] Cyclometalated platinum(II) and palladium(II) complex phosphorescent materials are ideal luminescent materials because their heavy atom effect can fully utilize all singlet and triplet excitons generated by electrical excitation, leading to a theoretical maximum quantum efficiency of 100%. Bidentate cyclometalated platinum(II) and palladium(II) complexes have low rigidity, and the two bidentate ligands tend to twist and vibrate, which causes the excited state of the material molecules to dissipate energy nonradiatively, resulting in a decrease in their luminescence quantum efficiency (Inorg. Chem. 2002, 41, 3055). On the other hand, tridentate cyclometalated platinum(II) and palladium(II) complexes have high luminescence quantum efficiency due to their improved molecular rigidity (Inorg. Chem. 2010, 49, 11276). However, the second monodentate ligand (Cl) contained in them results in a decrease in the luminescence quantum efficiency. -The presence of anions such as phenoxy anions, alkyne anions, and carbenes greatly reduces the chemical and thermal stability of the complexes, making it difficult to prepare OLED components by sublimation purification. This makes it difficult for both bidentate and tridentate cyclometalated complex emitting materials to be used in stable and efficient OLED components. The central metal ions of divalent cyclometalated platinum(II) and palladium(II) complexes are both dsp 2 The cyclometalated platinum(II) and palladium(II) complexes are hybrids that easily coordinate to tetradentate ligands to form stable, rigid, square-planar structures. Their high molecular rigidity suppresses nonradiative relaxation due to molecular vibration and rotation, reducing energy loss in excited states and thus improving the luminescence quantum efficiency of the materials. Due to the steric hindrance of the two aryl groups at the ends of the tetradentate ligands, the materials exhibit a twisted square structure (Chem. Mater. 2020, 32, 537). While theoretically possessing spirochirality, the molecules are prone to racemization in solution or during thermal sublimation due to the up-and-down vibration of the two aryl groups at the ends of the ligands, making it impossible to separate the enantiomers. Obtaining optically pure cyclometalated platinum(II) and palladium(II) complexes is extremely difficult, and they lack circularly polarized luminescence. Therefore, how to design and evolve optically pure cyclometalated platinum(II) and palladium(II) complex material molecules that have high chemical and thermal stability and circularly polarized emission properties is of great significance and practical value for their use in circularly polarized light-emitting OLED components (CP-OLEDs), and is also an urgent issue that needs to be resolved in the CP-OLED field. Summary of the Invention [Problem to be solved by the invention]

[0004] The present invention aims to provide a circularly polarized luminescent material and its use, which is a central chirality-induced spiro-chiral tetradentate cyclometalated platinum(II) and palladium(II) complex circularly polarized luminescent material, in response to the current lack of development of circularly polarized luminescent materials. The spiro-chiral metal complex molecule is characterized by the central chiral segment L of the tetradentate ligand. a As a result, the entire tetradentate ligand can be coordinated to the metal ion in a manner with little steric hindrance, spontaneously inducing the formation of an optically pure spiro-chiral metal complex circularly polarized luminescent material, which does not require chiral resolution and has high chemical and thermal stability, making it an important candidate for circularly polarized luminescent devices. [Means for solving the problem]

[0005] The object of the present invention is achieved by the following technical solutions: The circularly polarized luminescent materials are center-chirality-induced spiro-chirality tetradentate cyclometalated platinum(II) and palladium(II) complexes based on phenyl-benzimidazole and its derivatives, and are characterized as follows: Their chemical formulas are as shown in general formulas (1), (1'), (2), and (2'), where (1) and (1'), and (2) and (2') are enantiomers of each other; [ka] JPEG2025528613000003.jpg4280In the formula, M is Pt or Pd, and V 1 , V 2 , V 3 are each independently N or C; L a is a five-membered central chiral carbocyclic or heterocyclic ring, X is O, S, CR x R y , C=O, SiR x R y , GeR x R y , N.R. z , PR z , R z P=O, AsR z , Rz As=O, S=O, SO2, Se, Se=O, SeO2, BH, BR z , R z Bi=O or BiR z and Y is O, S, Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 are each independently N or C; R 1 , R 2 , R 3 , R 4 , R a , R b , R c , R d each independently represents mono-, di-, tri-, or tetra-substituted or unsubstituted, and R 1 , R 2 , R 3 , R 4 , R a , R b , R c , R dare each independently hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, aryl group, heteroalkyl group, heterocycloalkyl group, heteroaryl group, haloalkyl group, haloaryl group, haloheteroaryl group, alkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxy group, mercapto group, nitro group, cyano group, amino group, mono- or di-alkylamino group, mono- or diarylamino group, ester group, nitrile group, isonitrile group, heteroaryl group, alkoxycarbonyl group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, sulfinyl group, carbamide group, phosphoramide group, imine group, sulfo group, carboxy group, hydrazino group, substituted silyl group, or a combination thereof; a and R b are different substituents in the same molecule, and two or more adjacent R 1 , R 2 , R 3 and R 4 may optionally be bonded to form a fused ring, and R a , R b , R c and R d Any two of the functional groups may be linked to form a ring system.

[0006] Furthermore, the central chirality-induced spiro-chirality tetradentate cyclometallated platinum(II) and palladium(II) complex circularly polarized luminescent materials having the above general formulae (1), (1'), (2), and (2') are preferably represented by the following general formulae (1-A) and (2-A) and their enantiomers (1'-A) and (2'-A): [ka] JPEG2025528613000005.jpg4789In the formula, M is Pt or Pd, L a is a five-membered central chiral carbocyclic or heterocyclic ring, X is O, S, CR x Ry , C=O, SiR x R y , GeR x R y , N.R. z , PR z , R z P=O, AsR z , R z As=O, S=O, SO2, Se, Se=O, SeO2, BH, BR z , R z Bi=O or BiR z and Y is O, S, Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , Z 6 , Z 7 , Z 8 , Z 9 , Z 10 , Z 11 , Z 12 , Z 13 are each independently N or C; R 1 , R 2 , R 3 , R 4 , R a , R b , R c , R d each independently represents mono-, di-, tri-, or tetra-substituted or unsubstituted, and R 1 , R 2 , R 3 , R 4 , R a , R b , R c , R dare each independently hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, aryl group, heteroalkyl group, heterocycloalkyl group, heteroaryl group, haloalkyl group, haloaryl group, haloheteroaryl group, alkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxy group, mercapto group, nitro group, cyano group, amino group, mono- or di-alkylamino group, mono- or diarylamino group, ester group, nitrile group, isonitrile group, heteroaryl group, alkoxycarbonyl group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, sulfinyl group, carbamide group, phosphoramide group, imine group, sulfo group, carboxy group, hydrazino group, substituted silyl group, or a combination thereof; a and R b are different substituents in the same molecule, and two or more adjacent R 1 , R 2 , R 3 and R 4 may optionally be bonded to form a fused ring, and R a , R b , R c and R d Any two of the functional groups may be linked to form a ring system.

[0007] Furthermore, the L in the general structure of the central chirality-induced spirochiral tetradentate cyclometalated platinum (II) and palladium (II) complex circularly polarized luminescent material a may have the following structures, but is not limited to: [ka] JPEG2025528613000007.jpg14106In formula, R a1 , R a2 , R a3each independently represents hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, aryl group, heteroalkyl group, heterocycloalkyl group, heteroaryl group, haloalkyl group, haloaryl group, haloheteroaryl group, alkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxy group, mercapto group, nitro group, cyano group, amino group, mono- or di-alkylamino group, mono- or diarylamino group, ester group, nitrile group, isonitrile group, heteroaryl group, alkoxycarbonyl group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, sulfinyl group, carbamide group, phosphoramide group, imine group, sulfo group, carboxy group, hydrazino group, substituted silyl group, or a combination thereof; In the formula, R b1 , R c1 , R c2 each independently represents mono-, di-, tri-, or tetra-substituted or unsubstituted, and R b1 , R c1 , R c2 are each independently hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, aryl group, heteroalkyl group, heterocycloalkyl group, heteroaryl group, haloalkyl group, haloaryl group, haloheteroaryl group, alkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxy group, mercapto group, nitro group, cyano group, amino group, mono- or di-alkylamino group, mono- or diarylamino group, ester group, nitrile group, isonitrile group, heteroaryl group, alkoxycarbonyl group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, sulfinyl group, carbamide group, phosphoramide group, imine group, sulfo group, carboxy group, hydrazino group, substituted silyl group, or a combination thereof; b1 , R c1 and R c2 may optionally be bonded to form a fused ring.

[0008] Furthermore, the central chiral segment L a More specifically, may have the following structures, but is not limited thereto: [ka] JPEG2025528613000009.jpg149106JPEG2025528613000010.jpg16106In formula, R d1 represents mono-, di-, tri-, or tetra-substituted or unsubstituted, and R b1 are independently hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, aryl group, heteroalkyl group, heterocycloalkyl group, heteroaryl group, haloalkyl group, haloaryl group, haloheteroaryl group, alkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxy group, mercapto group, nitro group, cyano group, amino group, mono- or di-alkylamino group, mono- or diarylamino group, ester group, nitrile group, isonitrile group, heteroaryl group, alkoxycarbonyl group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, sulfinyl group, carbamide group, phosphoramide group, imine group, sulfo group, carboxy group, hydrazino group, substituted silyl group, or a combination thereof; d1 may optionally be bonded to form a fused ring, and R e1 , R e2 , R e3 , R e4independently represent hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, aryl group, heteroalkyl group, heterocycloalkyl group, heteroaryl group, haloalkyl group, haloaryl group, haloheteroaryl group, alkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxy group, mercapto group, nitro group, cyano group, amino group, mono- or di-alkylamino group, mono- or diarylamino group, ester group, nitrile group, isonitrile group, heteroaryl group, alkoxycarbonyl group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, sulfinyl group, carbamide group, phosphoramide group, imine group, sulfo group, carboxy group, hydrazino group, substituted silyl group, or a combination thereof.

[0009] Furthermore, the central chirality induced spiro-chirality tetradentate cyclometalated platinum(II) and palladium(II) complex circularly polarized luminescent material is preferably selected from, but not limited to, the following structures and their enantiomers: [ka] JPEG2025528613000012.jpg30106JPEG2025528613000013.jpg142106JPEG2025528613000014.jpg140106JPEG2025528613000015.jpg145106JPEG2025528613000016.jpg146106JPEG2025528613000017.jpg149106JPEG2025528613000018.jpg147106JPEG2025528613000019.jpg146106JPEG2025528613000020.jpg146106JPEG2025528613000021.jpg146106JPEG2025528613000022.jpg146106JPEG2025528613000023.jpg146106JPEG2025528613000024.jpg146106JPEG2025528613000025.jpg146106JPEG2025528613000026.jpg146106JPEG2025528613000027.jpg146106JPEG2025528613000028.jpg145106JPEG2025528613000029.jpg145106JPEG2025528613000030.jpg144106JPEG2025528613000031.jpg144106JPEG2025528613000032.jpg149106JPEG2025528613000033.jpg149106JPEG2025528613000034.jpg149106JPEG2025528613000035.jpg158106JPEG2025528613000036.In the formula (jpg156106), M is Pt or Pd, and R and R' are each independently hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, aryl group, heteroalkyl group, heterocycloalkyl group, heteroaryl group, haloalkyl group, haloaryl group, haloheteroaryl group, alkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxy group, mercapto group, nitro group, cyano group, amino group, mono- or di-alkylamino group, mono- or diarylamino group, ester group, nitrile group, isonitrile group, heteroaryl group, alkoxycarbonyl group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, sulfinyl group, carbamide group, phosphoramide group, imine group, sulfo group, carboxy group, hydrazino group, or substituted silyl group.

[0010] Furthermore, the present invention relates to the use of any of the spiro-chirality tetradentate cyclometalated platinum(II) and palladium(II) complex circularly polarized luminescent materials described above in light-emitting components, 3D display components, three-dimensional imaging components, optical information encryption components, information storage components, and bioimaging components.

[0011] Furthermore, the light emitting component is the above-mentioned component, wherein the light emitting component is a light emitting diode or a light emitting electrochemical cell.

[0012] Further, the present invention is a full color display characterized by including a light emitting component.

[0013] Furthermore, a light-emitting display component is characterized by including the light-emitting component according to claim 7.

[0014] Furthermore, the above use is characterized in that the light-emitting device comprises a first electrode, a second electrode, and at least one organic layer provided between the first electrode and the second electrode, and the organic layer comprises a spiro-chirality tetradentate cyclometallated platinum(II) and palladium(II) complex circularly polarized light-emitting material.

[0015] The present invention also provides a display device including an organic light-emitting element, wherein the organic light-emitting element includes a first electrode, a second electrode, and at least one organic layer provided between the first electrode and the second electrode, and the organic layer includes the spiro-chirality tetradentate cyclometalated platinum(II) and palladium(II) complex circularly polarized light-emitting material according to any one of claims 1 to 5. [Effects of the Invention]

[0016] The beneficial effects of the present invention are as follows: (1) The central chirality spontaneously induces the emergence of spiro-chirality. a A tetradentate ligand containing L was designed and developed. 3 or L 4 By utilizing the steric hindrance effect between the tetradentate cyclometalated platinum(II) and palladium(II) complexes, the entire molecule is given a twisted square structure, and the central chiral segment L a The tetradentate ligands coordinate to the metal ions in a manner with minimal steric hindrance, spontaneously inducing the formation of optically pure metal ion-centered spirochiral tetradentate cyclometalated platinum(II) and palladium(II) complex circularly polarized luminescent materials. See Figure 1.

[0017] (2) Optically pure raw materials are economical and readily available. a The two optically pure chiral isomers required for the preparation of the tetradentate ligand containing are both economical and readily available commercially, making it advantageous for the large-scale preparation of the two optically pure chiral tetradentate ligands.

[0018] (3) The circularly polarized luminescent material does not require chiral resolution. It is easy to produce circularly polarized luminescent materials from the two optically pure chiral tetradentate ligands mentioned above, which are the corresponding two optically pure chiral isomers of spiro-chiral tetradentate cyclometalated platinum(II) and palladium(II) complexes. This eliminates the need for purification by chiral column separation, and eliminates the limiting factor of high cost of chiral resolution, significantly reducing the production cost of the material.

[0019] (4) The chemical and thermal stability of the material is high. The designed and developed tetradentate ligand is dsp 2 It can coordinate well with the hybrid platinum(II) and palladium(II) metal ions to form a stable and rigid square-structure molecule, and its chemical stability is high. Furthermore, the designed central chiral ligand L a and another terminal ligand L 3 or L 4 Due to the large steric hindrance between the metal complex and the chiral tetradentate cyclometallate, the entire metal complex molecule can form a stable spirochiral tetradentate cyclometallate complex, which does not lose its circularly polarized luminescence property due to racemization either in solution or during high-temperature sublimation. [Brief explanation of the drawings]

[0020] [Figure 1] Figure 1 shows the design concept of a circularly polarized luminescent material based on a spiro-chiral tetradentate cyclometallate complex centered on an optically pure metal ion. [Figure 2] In Figure 2, (A) is a front view of the molecular structure of (R,S)-P-PtYL3 after optimization by DFT calculations, (B) is a plan view of the molecular structure of (R,S)-P-PtYL3 after optimization by DFT calculations, (C) is the molecular structural formula of (R,S)-P-PtYL3, (D) is a front view of the molecular structure of (R,S)-M-PtYL3 after optimization by DFT calculations, (E) is a plan view of the molecular structure of (R,S)-M-PtYL3 after optimization by DFT calculations, and (F) is the molecular structural formula of (R,S)-M-PtYL3. [Figure 3]Figure 3 shows the emission spectra of optically pure (R,S)-M-PtYL1 and (S,R)-P-PtYL1 in dichloromethane solution at room temperature in the absence of oxygen. [Figure 4] Figure 4 shows the emission spectra of optically pure (R,S)-M-PtYL2 and (S,R)-P-PtYL2 in dichloromethane solution at room temperature in the absence of oxygen. [Figure 5] FIG. 5 shows the emission spectra of optically pure (R,S)-M-PtYL3 and (S,R)-P-PtYL3 in dichloromethane solution at room temperature in the absence of oxygen. [Figure 6] Figure 6 shows the emission spectra of optically pure (R,S)-M-PtYL4 and (S,R)-P-PtYL4 in dichloromethane solution at room temperature in the absence of oxygen. [Figure 7] FIG. 7 shows the emission spectra of optically pure (R,S)-M-PtYL5 and (S,R)-P-PtYL5 in dichloromethane solution at room temperature in the absence of oxygen. [Figure 8] Figure 8 shows the emission spectra of optically pure (R,S)-M-PtYL6 and (S,R)-P-PtYL6 in dichloromethane solution at room temperature in the absence of oxygen. [Figure 9] Figure 9 shows the emission spectra of optically pure (R,S)-M-PdYL2 and (S,R)-P-PdYL2 in dichloromethane solution at room temperature in the absence of oxygen. [Figure 10] FIG. 10 shows the emission spectrum of optically pure (S,R)-P-PtYL35 in dichloromethane solution at room temperature in the absence of oxygen. [Figure 11] FIG. 11 shows a schematic diagram of the HOMO and LUMO orbital distributions and molecular structures of the compounds P-PtYL1, P-PtYL2, P-PtYL3, and P-PtYL4. [Figure 12]FIG. 12 shows the HOMO and LUMO orbital distribution diagrams and molecular structure formulas of the compounds P-PtYL5 (naphthalene ring facing inward), P-PtYL5 (naphthalene ring facing outward), and P-PtYL6. [Figure 13] FIG. 13 shows a schematic diagram of the HOMO and LUMO orbital distributions and molecular structures of compounds P-PtYL7, P-PtYL8, P-PtYL9, and P-PtYL10. [Figure 14] FIG. 14 shows the HOMO and LUMO orbital distribution diagrams and molecular structure formulas of the compounds P-PtYL11, P-PtYL12, P-PtYL13, and P-PtYL14. [Figure 15] FIG. 15 shows the HOMO and LUMO orbital distribution diagrams and molecular structure formulas of compounds P-PtYL15, P-PtYL16, P-PtYL17, and P-PtYL18. [Figure 16] FIG. 16 shows the HOMO and LUMO orbital distribution diagrams and molecular structure formulas of compounds P-PtYL19, P-PtYL20, P-PtYL21, and P-PtYL22. [Figure 17] FIG. 17 shows the HOMO and LUMO orbital distribution diagrams and molecular structure formulas of compounds P-PtYL23, P-PtYL24, P-PtYL25, and P-PtYL26. [Figure 18] FIG. 18 shows the HOMO and LUMO orbital distribution diagrams and molecular structure formulas of compounds P-PtYL27, P-PtYL28, P-PtYL29, and P-PtYL30. [Figure 19] FIG. 19 shows a schematic diagram of the HOMO and LUMO orbital distributions and molecular structure formulas of each of the compounds P-PtYL31, P-PtYL32, P-PtYL33, and P-PtYL34. [Figure 20] FIG. 20 shows the circular dichroism spectra of optically pure (R,S)-M-PtYL1 and (S,R)-P-PtYL1 in dichloromethane solution. [Figure 21] FIG. 21 shows the circular dichroism spectra of optically pure (R,S)-M-PtYL2 and (S,R)-P-PtYL2 in dichloromethane solution. [Figure 22] FIG. 22 shows the circular dichroism spectra of optically pure (R,S)-M-PtYL3 and (S,R)-P-PtYL3 in dichloromethane solution. [Figure 23] FIG. 23 shows the circular dichroism spectra of optically pure (R,S)-M-PtYL4 and (S,R)-P-PtYL4 in dichloromethane solution. [Figure 24] FIG. 24 shows the circular dichroism spectra of optically pure (R,S)-M-PtYL5 and (S,R)-P-PtYL5 in dichloromethane solution. [Figure 25] FIG. 25 shows the circular dichroism spectra of optically pure (R,S)-M-PtYL6 and (S,R)-P-PtYL6 in dichloromethane solution. [Figure 26] FIG. 26 shows the circularly polarized emission spectra of optically pure (R,S)-M-PtYL1 and (S,R)-P-PtYL1 in dichloromethane solution at room temperature in the absence of oxygen. [Figure 27] FIG. 27 shows the circularly polarized emission spectra of optically pure (R,S)-M-PtYL2 and (S,R)-P-PtYL2 in dichloromethane solutions at room temperature in the absence of oxygen. [Figure 28] FIG. 28 shows the circularly polarized emission spectra of optically pure (R,S)-M-PtYL3 and (S,R)-P-PtYL3 in dichloromethane solutions at room temperature in the absence of oxygen. [Figure 29] FIG. 29 shows the circularly polarized emission spectra of optically pure (R,S)-M-PtYL4 and (S,R)-P-PtYL4 in dichloromethane solutions at room temperature in the absence of oxygen. [Figure 30] FIG. 30 shows the circularly polarized emission spectra of optically pure (R,S)-M-PtYL6 and (S,R)-P-PtYL6 in dichloromethane solution at room temperature in the absence of oxygen. [Figure 31]Figure 31 shows the peak spectra by high-performance liquid chromatography (HPLC) of a mixture of optically pure (R,S)-M-PtYL6 and (S,R)-P-PtYL6, optically pure (R,S)-M-PtYL6 alone, and optically pure (S,R)-P-PtYL6 alone. [Figure 32] FIG. 32 is a structural schematic diagram of an organic light-emitting element. DETAILED DESCRIPTION OF THE INVENTION

[0021] The present invention will be described in detail below. The following description of the components may be based on typical embodiments or specific examples of the present invention, but the present invention is not limited to such embodiments or specific examples.

[0022] Specific examples of the circularly polarized light-emitting material of the present invention represented by the above general formula will be described below, but they should not be construed as limiting the present invention.

[0023] It is believed that the present disclosure will be more readily understood by reference to the following specific embodiments and the examples contained therein. Before beginning to disclose and describe the compounds, components, and / or methods of the present invention, it is understood that, unless otherwise specified, they are not limited to specific synthetic methods or specific reagents, as these may vary. It is also understood that the terminology used herein is used only to describe particular aspects and is not intended to be limiting. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention, exemplary methods and materials are described below.

[0024] As used in the specification and claims that follow, the singular terms "a," "an," "the ...

[0025] As used herein, the term "optional" or "optionally" means that the subsequently described event or circumstance may or may not occur, and the description includes instances where the event or circumstance occurred and instances where it did not occur.

[0026] Disclosed herein are components that can be used to prepare the compositions described herein, as well as the compositions themselves for use in the methods disclosed herein. It is understood that the present invention discloses these and other materials, as well as combinations, subcombinations, interactions, and groups of these substances. While the different individual combinations, their entirety, and specific sequences of each of these compounds cannot be specifically disclosed, each has its own consideration and explanation. For example, when a specific compound is disclosed and discussed, and many modifications that can be made to many molecules containing that compound are discussed, each combination, sequence, and possible modification of the compound is specifically contemplated unless a counter-possible modification is specifically indicated. Thus, the disclosure of examples of molecules A, B, and C, molecules D, E, and F, and a combination molecule AD, may be considered to disclose the individual combinations AE, AF, BD, BE, BF, CD, CE, and CF, as well as the entire combination, even if not individually described. Similarly, any subcombinations or combinations thereof are also disclosed. For example, the subcombination AE, BF, and CE is also disclosed. This concept applies to all aspects of the present invention, including, but not limited to, steps in the methods of making and using the compositions. Therefore, where there are various other possible steps, it should be understood that each of these other steps may be performed by a specific embodiment or combination of embodiments of the method.

[0027] The linking atom utilized in the present invention can have two functional groups attached to it, e.g., N and C. The linking atom can optionally have other chemical functional groups attached to it (if valence allows). For example, an oxygen atom cannot have any other chemical functional groups attached to it because it has no valence available when two atoms (e.g., N or C) are attached to it. In contrast, when a carbon is the linking atom, two other chemical functional groups can be attached to it. Suitable chemical functional groups include, but are not limited to, hydrogen, hydroxy, alkyl, alkoxy, =0, halogen, nitro, amine, amide, mercapto, aryl, heteroaryl, cycloalkyl, and heterocyclyl groups.

[0028] As used herein, the term "cyclic structure" or similar terms refers to any cyclic chemical structure, including, but not limited to, aryl groups, heteroaryl groups, cycloalkyl groups, cycloalkenyl groups, heterocyclyl groups, carbenes, and N-heterocyclic carbenes.

[0029] As used herein, the term "substituted" or similar terms includes all permissible substituents of organic compounds. Broadly defined, the permissible substituents include cyclic and acyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and nonaromatic substituents of organic compounds. For example, exemplary substituents include those described below. For appropriate organic compounds, the permissible substituents can be one or more and can be the same or different. Where consistent with the purposes of this invention, heteroatoms (e.g., nitrogen) can have hydrogen substituents and / or any permissible substituents of organic compounds described herein which satisfy the valences of the heteroatoms. This invention is not intended to be limited in any manner by the permissible substituents of organic compounds. Similarly, the implicit qualification included in the terms "substituted" or "substituted by" is that such substitution is compatible with the allowed valences of the substituted atom and the substituent, and that the substitution results in a stable compound (e.g., a compound that does not spontaneously transform by rearrangement, cyclization, elimination, etc.). In some embodiments, unless expressly indicated to the contrary, a single substituent may be further optionally substituted (i.e., further substituted or unsubstituted).

[0030] When defining various terms, the present invention uses "R 1 "," "R 2 "," "R 3 " and "R 4 " represents various specific substituents as a common symbol. These symbols are not limited to those disclosed in the present invention and may be any substituents, and when they are defined as some substituents in one example, they may be defined as some other substituents in another example.

[0031] The term "alkyl group" as used herein refers to a branched or unbranched saturated hydrocarbon group of 1 to 30 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, eicosyl, and tetracosyl groups. The alkyl group may be cyclic or acyclic. The alkyl group may be branched or unbranched. The alkyl group may also be substituted or unsubstituted. For example, the alkyl group may be substituted with one or more functional groups, including, but not limited to, optionally substituted alkyl groups, cycloalkyl groups, alkoxy groups, amino groups, ethers, halogens, hydroxy groups, nitro groups, silyl groups, sulfo-oxo functional groups, and mercapto groups, as described herein. A "lower alkyl" functional group is an alkyl group containing from 1 to 6 (eg, 1 to 4) carbon atoms.

[0032] Throughout the specification, the term "alkyl group" generally refers to both unsubstituted and substituted alkyl groups; however, in the present invention, substituted alkyl groups are specifically referred to by identifying the specific substituents on the alkyl group. For example, the term "halogenated alkyl group" or "haloalkyl group" specifically refers to an alkyl group substituted with one or more halogens (e.g., fluorine, chlorine, bromine, or iodine). The term "alkoxyalkyl group" specifically refers to an alkyl group substituted with one or more alkoxy groups, as described below. The term "alkylamino group" specifically refers to an alkyl group substituted with one or more amino groups, as described below. When "alkyl group" is used in one case and a specific term such as "alkyl alcohol" is used in another case, it is not intended to refer to the specific term such as "alkyl alcohol" when a term that is partially different from the term "alkyl group" is used.

[0033] Such considerations also apply to other functional groups described in the present invention. That is, when a term such as "cycloalkyl group" refers to both unsubstituted and substituted cycloalkyl group moieties, the substituted moieties may be specifically defined elsewhere in the present invention; for example, a specific substituted cycloalkyl group may be specifically referred to as an "alkylcycloalkyl group." Similarly, a substituted alkoxy group may be specifically referred to as a "haloalkoxy group," and a specific substituted alkenyl group may be an "enol." Similarly, when a common term such as "cycloalkyl group" or a specific term such as "alkylcycloalkyl group" is used, it is not intended to include the specific term when a term that is partially different from the common term is used.

[0034] The term "cycloalkyl group" as used herein refers to a non-aromatic carbocyclic ring of 3 to 30 carbon atoms, composed of at least three carbon atoms. Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclononyl groups. The term "heterocycloalkyl group" refers to a type of cycloalkyl group defined above and included within the term "cycloalkyl group," in which at least one ring carbon atom is replaced by a heteroatom, such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus. Such cycloalkyl and heterocycloalkyl groups may be substituted or unsubstituted. Such cycloalkyl and heterocycloalkyl groups may be substituted with one or more functional groups, including, but not limited to, alkyl, cycloalkyl groups, alkoxy groups, amino groups, ethers, halogens, hydroxy groups, nitro groups, silyl groups, sulfo-oxo functional groups, and mercapto groups, as described herein.

[0035] As used herein, the term "polyolefin functional group" refers to a functional group containing two or more CH functional groups bonded together. A "polyolefin functional group" is a -(CH) a-, where "a" is an integer between 2 and 500.

[0036] The terms "alkoxy group" and "alkoxy functional group" as used herein refer to an alkyl or cycloalkyl group of 1 to 30 carbon atoms bonded by an ether bond, i.e., an "alkoxy group" is -OR 1 may be defined as, where R 1 is an alkyl or cycloalkyl group as defined above. The term "alkoxy group" also includes the alkoxy polymers described above, i.e., an alkoxy group is an alkyl group or a cycloalkyl group, as defined above. 1 -OR 2 -OR 1 -(OR 2 ) a -OR 3 where "a" is an integer from 1 to 500, and R 1 , R 2 , R 3 is each independently an alkyl group, a cycloalkyl group, or a combination thereof.

[0037] As used herein, the term "alkenyl group" refers to a hydrocarbon group of 2 to 30 carbon atoms, the structural formula of which contains at least one carbon-carbon double bond. (R 1 R 2 )C=C(R 3 R 4 ) include E and Z isomers. Thus, in the structural formulae of the present invention, the presence of an asymmetric olefin may be presumed or may be explicitly indicated by the bond symbol C=C. The alkenyl group may be substituted with one or more functional groups, including, but not limited to, alkyl groups, cycloalkyl groups, alkoxy groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, cycloalkynyl groups, aryl groups, heteroaryl groups, aldehydes, amino groups, carboxylic acids, esters, ethers, halogens, hydroxy groups, ketones, azide groups, nitro groups, silyl groups, sulfo-oxo functional groups, or mercapto groups, as described herein.

[0038] The term "cycloalkenyl group" as used herein refers to a non-aromatic carbocyclic ring of 3 to 30 carbon atoms, consisting of at least three carbon atoms and containing at least one carbon-carbon double bond, i.e., C=C. Examples of cycloalkenyl groups include, but are not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, and cycloheptenyl. The term "heterocycloalkenyl group" refers to a type of cycloalkenyl group defined above and is included within the term "cycloalkenyl group," in which at least one carbon atom in the ring is replaced by a heteroatom, such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus. Cycloalkenyl and heterocycloalkenyl groups may be substituted or unsubstituted. The cycloalkenyl and heterocycloalkenyl groups may be substituted with one or more functional groups, including, but not limited to, alkyl groups, cycloalkyl groups, alkoxy groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, cycloalkynyl groups, aryl groups, heteroaryl groups, aldehydes, amino groups, carboxylic acids, esters, ethers, halogens, hydroxy groups, ketones, azide groups, nitro groups, silyl groups, sulfo-oxo functional groups, or mercapto groups, as described herein.

[0039] The term "alkynyl group" as used herein refers to a hydrocarbon group having 2 to 30 carbon atoms and whose structural formula contains at least one carbon-carbon triple bond. The alkynyl group may be unsubstituted or substituted with one or more functional groups, including, but not limited to, alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halogen, hydroxy, ketone, azide, nitro, silyl, sulfo-oxo functional group, or mercapto group, as described herein.

[0040] The term "cycloalkynyl group" as used herein refers to a non-aromatic carbon ring containing at least seven carbon atoms and at least one carbon-carbon triple bond. Examples of cycloalkynyl groups include, but are not limited to, cycloheptynyl, cyclooctynyl, and cyclononenyl groups. The term "heterocycloalkynyl group" refers to a type of cycloalkenyl group defined above and included within the term "cycloalkynyl group," in which at least one of the ring carbon atoms is replaced by a heteroatom, such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus. Cycloalkynyl and heterocycloalkynyl groups can be substituted or unsubstituted. The cycloalkynyl and heterocycloalkynyl groups may be substituted with one or more functional groups, including, but not limited to, alkyl groups, cycloalkyl groups, alkoxy groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, cycloalkynyl groups, aryl groups, heteroaryl groups, aldehydes, amino groups, carboxylic acids, esters, ethers, halogens, hydroxy groups, ketones, azide groups, nitro groups, silyl groups, sulfo-oxo functional groups, or mercapto groups, as described herein.

[0041] As used herein, the term "aryl group" refers to any carbon-based aromatic functional group containing up to 60 carbon atoms, including, but not limited to, phenyl, naphthyl, biphenyl, phenoxyphenyl, anthryl, and phenanthryl groups. The term "aryl group" also includes "heteroaryl groups," which are defined as containing an aromatic functional group, but which contain at least one heteroatom in the ring of the aromatic functional group. Examples of heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, or phosphorus. Similarly, the term "non-heteroaryl group" (also included in the term "aryl group") is defined as containing an aromatic functional group, but which does not contain a heteroatom. Aryl groups may be substituted or unsubstituted. The aryl group may be substituted with one or more functional groups, including, but not limited to, alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxylic acid, ester, ether, halogen, hydroxy, ketone, azide, nitro, silyl, sulfo-oxo functional group, or mercapto groups, as described herein. The term "biaryl group" is a specific type of aryl group and is included in the definition of "aryl group." A biaryl group refers to two aryl groups linked by a fused ring structure, such as naphthalene, or two aryl groups linked by one or more carbon-carbon bonds, such as biphenyl.

[0042] As used herein, the term "aldehyde" is represented by the formula -C(O)H. Throughout the specification, "C(O)" is a shorthand notation for a carbonyl group (i.e., C=O).

[0043] As used herein, the term "amine" or "amino group" refers to a group of the formula -NR 1 R 2 where R 1 , R 2may be independently selected from hydrogen, an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a cycloalkynyl group, an aryl group, or a heteroaryl group.

[0044] The term "alkylamino group" as used herein is represented by a group of the formula -NH(-alkyl), wherein the alkyl group is as defined herein. Representative examples include, but are not limited to, methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, isobutylamino group, sec-butylamino group, tert-butylamino group, pentylamino group, isopentylamino group, tert-pentylamino group, hexylamino group, and the like.

[0045] The term "dialkylamino group" as used herein is represented by a group of the formula -N(-alkyl)2, where the alkyl group is as defined herein. Representative examples include, but are not limited to, dimethylamino group, diethylamino group, dipropylamino group, diisopropylamino group, dibutylamino group, diisobutylamino group, di-sec-butylamino group, di-tert-butylamino group, dipentylamino group, diisopentylamino group, di-tert-pentylamino group, dihexylamino group, N-ethyl-N-methylamino group, N-methyl-N-propylamino group, N-ethyl-N-propylamino group, and the like.

[0046] The term "carboxylic acid" as used herein is represented by the formula -C(O)OH.

[0047] The term "ester" as used herein refers to an ester of the formula -OC(O)R 1 or -C(O)OR 1 where R 1 may be an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a cycloalkynyl group, an aryl group, or a heteroaryl group according to the present invention. The term "polyester" as used in the present invention refers to a group of aromatic hydrocarbons having the formula -(R1 O(O)CR 2 -C(O)O) a -or-(R 1 O(O)CR 2 -OC(O)) a - where R 1 , R 2 may independently be an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a cycloalkynyl group, an aryl group, or a heteroaryl group according to the present invention, and "a" is an integer from 1 to 500. The term "polyester" is used to describe a functional group produced by the reaction of a compound having at least two carboxy groups with a compound having at least two hydroxy groups.

[0048] The term "ether" as used herein refers to a group of the formula R 1 OR 2 where R 1 , R 2 may independently be an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a cycloalkynyl group, an aryl group, or a heteroaryl group as described herein. The term "polyether" as used herein refers to a group of 1 OR 2 O) a - where R 1 , R 2 may independently be an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a cycloalkynyl group, an aryl group, or a heteroaryl group as described herein, and "a" is an integer of 1 to 500. Examples of polyether functional groups include polyoxyethylene, polyoxypropylene, and polyoxybutylene.

[0049] As used herein, the term "halogen" refers to the halogens fluorine, chlorine, bromine, and iodine.

[0050] As used herein, the term "heterocyclyl group" refers to monocyclic and polycyclic non-aromatic ring systems of 3 to 30 carbon atoms, and as used herein, "heteroaryl group" refers to monocyclic and polycyclic aromatic ring systems of up to 60 carbon atoms, provided that at least one of the ring atoms is not carbon. This term includes azetidinyl, dioxanyl, furyl, imidazolyl, isothiazolyl, isoxazolyl, morpholinyl, oxazolyl (including 1,2,3-oxadiazolyl, 1,2,5-oxadiazolyl, and 1,3,4-oxadiazolyl), piperazinyl, piperidinyl, pyrazinyl, pyrazolyl, pyridazinyl, pyridinyl, pyrimidinyl, pyrrolyl, pyrrolidinyl, tetrahydrofuryl, tetrahydropyranyl, tetrazinyl, and the like. Examples of such groups include thiadiazolyl groups (including 1,2,4,5-tetrazinyl groups), tetrazolyl groups (including 1,2,3,4-tetrazolyl groups and 1,2,4,5-tetrazolyl groups), thiadiazolyl groups (including 1,2,3-thiadiazolyl groups, 1,2,5-thiadiazolyl groups and 1,3,4-thiadiazolyl groups), thiazolyl groups, thienyl groups, triazinyl groups (including 1,3,5-triazinyl groups and 1,2,4-triazinyl groups), and triazolyl groups (including 1,2,3-triazolyl groups and 1,3,4-triazolyl groups).

[0051] The term "hydroxy group" as used herein is represented by the formula -OH.

[0052] The term "ketone" as used herein refers to a compound of formula R 1 C(O)R 2 where R 1 , R 2 may independently be an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a cycloalkynyl group, an aryl group, or a heteroaryl group as described in this invention.

[0053] The term "azido group" as used herein is represented by the formula -N3.

[0054] The term "nitro group" as used herein is represented by the formula -NO2.

[0055] The term "nitrile" as used herein is represented by the formula -CN.

[0056] As used herein, the term "silyl group" refers to a group of the formula -SiR 1 R 2 R 3 where R 1 , R 2 , R 3 may independently be hydrogen or an alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl group as described herein.

[0057] As used herein, the term "sulfo-oxo functional group" refers to a group of the formula -S(O)R 1 , -S(O)2R 1 , -OS(O)2R 1 or -OS(O)2OR 1 where R 1 may be hydrogen or an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl or heteroaryl group as defined herein. Throughout the specification, "S(O)" is an abbreviation for S=O. As used herein, the term "sulfonyl group" refers to a group of the formula -S(O)R 1 where R 1 may be an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a cycloalkynyl group, an aryl group, or a heteroaryl group. As used herein, the term "sulfone" refers to a group of the formula R 1 S(O)2R 2 where R 1 , R 2may independently be an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a cycloalkynyl group, an aryl group, or a heteroaryl group as described herein. The term "sulfoxide" as used herein refers to a group of the formula R 1 S(O)R 2 where R 1 , R 2 may independently be an alkyl group, a cycloalkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a cycloalkynyl group, an aryl group, or a heteroaryl group as described in this invention.

[0058] The term "mercapto group" as used herein is represented by the formula -SH.

[0059] As used in the present invention, "R 1 "," "R 2 "," "R 3 "," "R n " (where n is an integer) may independently have one or more of the functional groups listed above. For example, R 1 When is a straight-chain alkyl group, one hydrogen atom of the alkyl group may optionally be replaced by a hydroxy group, an alkoxy group, an alkyl group, a halogen, etc. Depending on the functional group selected, the first functional group may be incorporated into the second functional group, or the first functional group may be a pendant group of (i.e., attached to) the second functional group. For example, for the term "an alkyl group comprising an amino group," the amino group may be incorporated into the backbone of the alkyl group. Optionally, the amino group may be attached to the backbone of the alkyl group. The nature of the functional group selected will dictate whether the first functional group is incorporated into or attached to the second functional group.

[0060] The compounds described herein may contain "optionally substituted" moieties. In general, the term "substituted" (whether preceded by the term "optionally") means that one or more hydrogen atoms of the moiety are replaced with a suitable substituent. Unless otherwise specified, an "optionally substituted" functional group may have a suitable substituent at each substitutable position of the functional group, and when more than one position in a given structure may be substituted with one or more substituents selected from a given functional group, the substituents at each position may be the same or different. Combinations of substituents contemplated by the present invention are preferably those that result in stable or chemically feasible compounds. In some embodiments, unless expressly indicated to the contrary, it is also contemplated that each substituent may be further optionally substituted (i.e., further substituted or unsubstituted).

[0061] The structure of the compound may be represented by the following formula: [ka] This may be understood to be equivalent to the following equation: [ka] where n is generally an integer, i.e., R n is five single substituents R n(a) , R n(b) , R n(c) , R n(d) , R n(e) "Single substituent" refers to the fact that each R substituent may be independently defined. For example, in some cases, R n(a) In such cases, when R is a halogen, n(b) is not necessarily a halogen.

[0062] The chemical structures and units disclosed and described in this invention include R 1 , R 2 , R 3 , R 4 , R 5, R 6 etc. are mentioned multiple times. 1 , R 2 , R 3 , R 4 , R 5 , R 6 Unless otherwise stated, any statements regarding 1 , R 2 , R 3 , R 4 , R 5 , R 6 Suitable for any structure or unit that refers to the same.

[0063] The term "fused ring" as used herein refers to a 5- or 6-membered aromatic ring or heteroaromatic ring to which two adjacent substituents can be fused, such as a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a metadiazaheterocycle, or a saturated 6- or 7-membered carbocyclic or carboheterocyclic ring.

[0064] Optoelectronic components using organic materials are becoming increasingly necessary for a variety of reasons. Because many of the materials needed to fabricate such devices are inexpensive, organic photovoltaic devices potentially offer cost advantages comparable to inorganic devices. Furthermore, the inherent properties of organic materials, such as their flexibility, make them well suited for specialized applications, such as fabrication on flexible substrates. Examples of organic optoelectronic components include organic light-emitting devices (OLEDs), organic phototransistors, organic solar cells, and organic photodetectors. In the case of OLEDs, organic materials may offer performance advantages over conventional materials. For example, the emission wavelength of the organic emissive layer can generally be easily tuned using appropriate dopants.

[0065] When an exciton decays from a singlet excited state to the ground state, resulting in instantaneous light emission, this is called fluorescence. When an exciton decays from a triplet excited state to the ground state, this is called phosphorescence. Because strong spin-orbit coupling between the singlet and triplet excited states of heavy metal atoms effectively enhances intersystem crossing (ISC), phosphorescent metal complexes (e.g., platinum complexes) have shown the potential to simultaneously utilize singlet and triplet excitons and achieve 100% internal quantum efficiency. Therefore, phosphorescent metal complexes are good candidates for dopants in the emissive layer of organic light-emitting devices (OLEDs) and have already attracted considerable attention in both academic and industrial fields. Numerous achievements over the past decade have led to the commercialization of this technology; for example, OLEDs are used in high-performance displays in smartphones, televisions, and digital cameras.

[0066] However, blue electroluminescent devices remain the most challenging area of ​​technology, and the stability of blue devices is one of the major challenges. It has been proven that the selection of host materials is crucial for the stability of blue devices. However, the minimum energy of the triplet excited state (T1) of blue-emitting materials is very high, which means that the minimum energy of the triplet excited state (T1) of the host material for blue devices is even higher. This makes the development of host materials for blue devices even more difficult.

[0067] The metal complexes of the present invention may be customized or tailored for specific applications with specific emission or absorption properties. The optical properties of the metal complexes of the present disclosure may be tailored by modifying the structure of the ligands surrounding the metal center or by modifying the structure of the fluorescent emitter on the ligand. For example, metal complexes with electron-donating or electron-withdrawing substituents on the ligands generally exhibit different optical properties in emission and absorption spectra. The color of the metal complex may be tailored by modifying the fluorescent emitter and the conjugated functional groups on the ligand.

[0068] The emission of such complexes of the present invention may be tuned, for example, from ultraviolet to near-infrared, by modifying the structure of the ligand or fluorescent emitter. Fluorescent emitters are atomic groups in organic molecules that can absorb energy to generate a singlet excited state, which quickly decays to produce instantaneous light emission. In one embodiment, the complexes of the present invention can provide a majority of their emission in the visible spectrum. In a specific example, the complexes of the present invention can emit light in the range of about 400 nm to about 700 nm. In another embodiment, the complexes of the present invention have improved stability and efficiency compared to conventional light-emitting complexes. Furthermore, the complexes of the present invention may be used, for example, as luminescent labels for biological applications (e.g., as anticancer drugs), as emitters in organic light-emitting diodes (OLEDs), or combinations thereof. In another embodiment, the complexes of the present invention may be used in light-emitting components, such as compact fluorescent lamps (CFLs), light-emitting diodes (LEDs), incandescent lamps, or combinations thereof.

[0069] Disclosed herein are platinum-containing compounds or complexes. The terms "compound" and "complex" are used interchangeably herein. The compounds disclosed herein have a neutral charge.

[0070] The compounds disclosed herein can exhibit desirable properties and have emission and / or absorption spectra that can be tuned with the selection of appropriate ligands. Additionally, the present invention may exclude any one or more compounds, structures, or portions thereof specifically described herein.

[0071] The compounds disclosed herein are suitable for a variety of optical and electro-optical devices, including, but not limited to, light absorbing devices (e.g., solar-powered devices, photosensitive devices), organic light emitting diodes (OLEDs), light emitting components or components capable of both absorbing and emitting light, and markers for biological applications.

[0072] As mentioned above, the disclosed compounds are platinum complexes. The compounds disclosed herein may also be used as host materials for OLEDs, such as full-color displays.

[0073] The compounds disclosed herein may be used in a variety of applications: As light-emitting materials, the compounds may be used in organic light-emitting diodes (OLEDs), light-emitting devices, displays, and other light-emitting components.

[0074] The compounds of the present invention may be made in a variety of ways, including but not limited to those described in the examples provided herein.

[0075] The compounds disclosed herein may be delayed fluorescence and / or phosphorescence emitters. In one embodiment, the compounds disclosed herein may be delayed fluorescence emitters. In one embodiment, the compounds disclosed herein may be phosphorescence emitters. In another embodiment, the compounds disclosed herein may be delayed fluorescence emitters and phosphorescence emitters.

[0076] The present disclosure relates to polydentate dinuclear cyclometallated platinum complexes that may be used as emissive and host materials in OLED components.

[0077] Unless otherwise specified, all commercially available reagents used in the following tests were used directly after purchase without further purification. 1 H NMR spectrum and 13 All C NMR spectra were measured in deuterated chloroform (CDCl3) or deuterated dimethyl sulfoxide (DMSO-d6) solutions. 1 For H NMR spectra, a 400 or 500 MHz nuclear magnetic resonance spectrometer was used. 13 C NMR spectra were obtained using a 100 or 126 MHz nuclear magnetic resonance instrument, with chemical shifts referenced to tetramethylsilane (TMS) or residual solvent. 1 H NMR spectrum, 13The C NMR spectra were measured using TMS (δ = 0.00 ppm) and CDCl3 (δ = 77.00 ppm) as internal standards. When DMSO-d6 was used as the solvent, 1 H NMR spectrum, 13 The C NMR spectra are based on TMS (δ = 0.00 ppm) and DMSO-d (δ = 39.52 ppm) as internal standards. The abbreviations (or combinations) are: s = singlet, d = doublet, t = triplet, q = quartet, p = quintet, m = multiplet, and br = broad line. 1 The H NMR spectrum peaks are submitted for interpretation. High-resolution mass spectra were measured on an Applied Biosystems ESI-QTOF mass spectrometer, with the sample ionization mode being electrospray ionization.

[0078] Example 1: Synthesis of Intermediate Bromides and Boronates, Key Chiral Segments [ka] (1) Synthesis of intermediate chiral 1-Br: 3-bromobenzonitrile (10 g, 54.94 mmol, 1.0 equiv.) and sodium methoxide (297 mg, 5.49 mmol, 0.1 equiv.) were added in this order to a single-neck flask equipped with a stirrer and allowed to react for 1 day with stirring at room temperature. Acetic acid was added until the solid disappeared, and the solvent was removed by distillation under reduced pressure to obtain crude product A. (1R,2S)-1-amino-2,3-dihydro-1H-inden-2-ol (3.28 g, 21.97 mmol, 0.4 equiv.) and absolute ethanol (30 mL) were added, and the mixture was allowed to react for 1.5 days with stirring in an oil bath at 85 °C. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether: ethyl acetate = 50:1 to 10:1 to obtain the product 2-Br, which was a white solid (5.74 g) with a yield of 83%. 1H NMR(500MHz,CDCl3):δ 3.41(d,J=18.5Hz,1H),3.52-3.57(m,1H),5.59(s,1H),5.81(d,J=3.0Hz, 1H), 7.27-7.31(m, 4H), 7.60-7.65(m, 2H), 7.98-8.00(m, 1H), 8.13(s, 1H).

[0079] (2) Synthesis of the intermediate chiral 1-Bpin. 1-Br (4.00 g, 12.70 mmol, 1.0 equiv.), bis(pinacolato)diboron (4.85 g, 19.10 mmol, 1.5 equiv.), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (186 mg, 0.26 mmol, 0.02 equiv.), and potassium acetate (3.74 g, 38.10 mmol, 3.0 equiv.) were added in this order to a 120 mL dry sealed tube equipped with a stirrer, and the tube was purged with nitrogen three times. Dimethyl sulfoxide (60 mL) was then added under nitrogen protection. The sealed tube was placed in an 85°C oil bath and stirred for 2 days. The mixture was then cooled to room temperature, washed with water, and extracted with ethyl acetate. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed once with saline, dried over anhydrous sodium sulfate, filtered, and the solvent removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography using a mixture of petroleum ether and ethyl acetate in a ratio of 15:1 to 10:1 to obtain 4.10 g of the product 1-Bpin as a white solid in a 91% yield. 1 H NMR(400MHz,DMSO-d6)δ 1.29(s,12H),3.24-3.28(m,1H),3.50(dd,J=18.0,6.8Hz,1H),5.49-5.56(m,1H),5.71(d,J=7.6Hz ,1H),7.23-7.31(m,3H),7.42-7.50(m,2H),7.78(d,J=7.2Hz,1H),7.98-7.91(m,1H),8.16(s,1H).

[0080] (3) Synthesis of intermediate 2-Br: 3-bromobenzonitrile (10 g, 54.94 mmol, 1.0 equiv.) and sodium methoxide (297 mg, 5.49 mmol, 0.1 equiv.) were added in this order to a single-neck flask equipped with a stirrer, and the mixture was stirred at room temperature for 1 day. Acetic acid was added until the solid disappeared, and the solvent was removed by distillation under reduced pressure to obtain crude product A. (1S,2R)-1-amino-2,3-dihydro-1H-inden-2-ol (4.10 g, 27.47 mmol, 0.5 equiv.) and absolute ethanol (30 mL) were added, and the mixture was stirred in an oil bath at 85 °C for 1.5 days. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether: ethyl acetate = 50:1 to 10:1 to obtain the product 1-Br, which was a white solid (5.60 g) with a yield of 65%. 1 H NMR(500MHz,CDCl3):δ 3.40(d,J=18.0Hz,1H),3.51-3.56(m,1H),5.57(t,J=7.5Hz,1H),7.79(d,J=8.0Hz,1H ),7.26-7.31(m,4H),7.59-7.63(m,2H),7.96(d,J=8.0Hz,1H),8.12(t,J=2.0Hz,1H).

[0081] (4) Synthesis of intermediate chiral 2-Bpin. 2-Br (4.00 g, 12.70 mmol, 1.0 equiv.), bis(pinacolato)diboron (4.85 g, 19.10 mmol, 1.5 equiv.), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (186 mg, 0.26 mmol, 0.02 equiv.), and potassium acetate (3.74 g, 38.10 mmol, 3.0 equiv.) were added in this order to a 120 mL dry sealed tube equipped with a stirrer, and the tube was purged with nitrogen three times. Dimethyl sulfoxide (60 mL) was then added under nitrogen protection. The sealed tube was placed in an 85°C oil bath and stirred for 2 days. The mixture was then cooled to room temperature, washed with water, and extracted with ethyl acetate. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed once with saline, dried over anhydrous sodium sulfate, filtered, and the solvent removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography using a mixture of petroleum ether and ethyl acetate in a ratio of 15:1 to 10:1 to obtain 4.21 g of the product 2-Bpin as a white solid in a 92% yield. 1 H NMR(400MHz,DMSO-d6)δ 1.29(s,12H),3.24-3.28(m,1H),3.50(dd,J=18.0,6.8Hz,1H),5.49-5.56(m,1H),5.71(d,J=7.6Hz ,1H),7.23-7.31(m,3H),7.42-7.50(m,2H),7.78(d,J=7.2Hz,1H),7.98-7.91(m,1H),8.16(s,1H).

[0082] Example 2: Tetradentate cyclometalated platinum(II) complex P-PtYL1 The synthetic route was as follows: [ka] (1) Synthesis of intermediate (S,R)-YL1. 2-Bpin (325 mg, 0.90 mmol, 1.0 equiv.), Ph-Oxa-Br (261 mg, 0.90 mmol, 1.0 equiv.), tetrakis(triphenylphosphine)palladium(0) (31 mg, 0.03 mmol, 0.03 equiv.), and potassium carbonate (373 mg, 2.7 mmol, 3.0 equiv.) were added in this order to a dry Schlenk tube equipped with a stirrer, and the mixture was purged with nitrogen three times. Then, dioxane (6 mL) and water (1 mL) were added under nitrogen protection. The Schlenk tube was placed in an oil bath at 85 °C and the reaction was continued for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether: ethyl acetate = 10:1 to obtain the product (S,R)-YL1, 358 mg of a white solid, with a yield of 90%. 1 H NMR(500MHz,DMSO-d6):δ(ppm) 3.31-3.32(m,1H),3.54(dd,J=18.0,7.0Hz,1H),5.57-5.60(m,1H),5.77(d,J=8.0Hz,1H),7.10- 7.13(m,1H),7.16(dd,J=8.5,0.5Hz,1H),7.27-7.30(m,2H),7.32-7.34(m,1H),7.54-7.60(m,2H) ,7.65(d,J=7.5Hz,1H),7.72(dd,J=8.0,1.0Hz,1H),7.88(dd,J=8.0,1.0Hz,1H),7.93(dt,J=8.0 ,1.0Hz,1H),8.06(dd,J=8.0,1.5Hz,1H),8.10-8.12(m,1H),8.54(t,J=1.5Hz,1H),11.12(s,1H).

[0083] (2) Synthesis of P-PtYL1. (S,R)-YL1 (250 mg, 0.56 mmol, 1.0 equiv.), potassium chloroplatinate (245 mg, 0.59 mmol, 1.05 equiv.), and tetrabutylammonium bromide (18 mg, 0.056 mmol, 10 mol%) were added to a dry 50 mL three-neck flask equipped with a stirrer and a condenser, in that order. The flask was then purged with nitrogen three times, and 30 mL of acetic acid (pre-bubbled with nitrogen) was added. After 30 minutes of nitrogen bubbling, the reaction mixture was stirred at room temperature for 12 hours, then at 120 °C for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:dichloromethane=1:1 to obtain the product P-PtYL1, 237 mg of a pale yellow solid, with a yield of 66%. 1 H NMR(500MHz,CDCl3):δ(ppm) 3.59(d,J=18.0Hz,1H),3.67(dd,J=18.0,6.5Hz,1H),5.93-5.96(m,1H),6.02(d,J =7.5Hz,1H),6.83-6.86(m,1H),7.28-7.30(m,4H),7.39(dd,J=8.5,1.0Hz,1H),7.4 3(dd,J=7.5,1.0Hz,1H),7.50(t,J=8.0Hz,1H),7.57-7.60(m,2H),8.10(d,J=8.0H z,1H),8.17(dd,J=8.5,1.0Hz,1H),8.25(dd,J=8.0,1.5Hz,1H),8.42-8.45(m,1H).

[0084] Example 3: Tetradentate cyclometalated platinum(II) complex M-PtYL1 The synthetic route was as follows: [ka] (1) Synthesis of intermediate (R,S)-YL1. 1-Bpin (672 mg, 1.86 mmol, 1.0 equiv.), Ph-Oxa-Br (540 mg, 1.86 mmol, 1.0 equiv.), tetrakis(triphenylphosphine)palladium(0) (65 mg, 0.06 mmol, 0.03 equiv.), and potassium carbonate (772 mg, 5.58 mmol, 3.0 equiv.) were added in this order to a dry Schlenk tube equipped with a stirrer. The tube was purged with nitrogen three times, and then dioxane (8 mL) and water (2 mL) were added under nitrogen protection. The Schlenk tube was placed in an oil bath at 85 °C and stirred for 2 days. The reaction was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether: ethyl acetate = 10:1 to obtain the product (R,S)-YL1, which was a white solid (797 mg) with a yield of 93%. 1 H NMR(400MHz,DMSO-d6):δ(ppm) 3.30-3.38(m,1H),3.54(dd,J=18.0,6.8Hz,1H),5.56-5.60(m,1H),5.76-5.78(m,1H ),7.09-7.13(m,1H),7.16(d,J=8.4Hz,1H),7.26-7.34(m,3H),7.48-7.60(m,3H),7. 65(t,J=8.0Hz,1H),7.72(d,J=7.6Hz,1H),7.88(d,J=8.0Hz,1H),7.92-7.94(m,1H), 8.06(dd,J=8.0,1.6Hz,1H),8.10-8.12(m,1H),8.54(t,J=1.6Hz,1H),11.13(s,1H).

[0085] (2) Synthesis of M-PtYL1. To a dry 50 mL three-neck flask equipped with a stirrer and a condenser, (R,S)-YL1 (250 mg, 0.56 mmol, 1.0 equiv.), potassium chloroplatinate (245 mg, 0.59 mmol, 1.05 equiv.), and tetrabutylammonium bromide (18 mg, 0.056 mmol, 10 mol%) were added in this order. The flask was then purged with nitrogen three times, and 30 mL of acetic acid (pre-bubbled with nitrogen) was added. After bubbling nitrogen through the reaction mixture for 30 minutes, the mixture was stirred at room temperature for 12 hours and then at 120 °C for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:dichloromethane=1:1 to obtain the product M-PtYL1, 213 mg of a pale yellow solid, with a yield of 60%. 1 H NMR(500MHz,CDCl3):δ(ppm) 3.59(d,J=18.0Hz,1H),3.67(dd,J=18.5,6.5Hz,1H),5.93-5.96(m,1H),6.02(d,J =7.5Hz,1H),6.83-6.86(m,1H),7.24-7.30(m,4H),7.39(dd,J=8.5,1.0Hz,1H),7.4 3(dd,J=7.5,1.0Hz,1H),7.50(t,J=8.0Hz,1H),7.57-7.60(m,2H),8.10(d,J=8.0H z,1H),8.17(dd,J=8.5,1.0Hz,1H),8.25(dd,J=8.0,1.5Hz,1H),8.42-8.45(m,1H).

[0086] Example 4: Tetradentate cyclometalated platinum(II) complex P-PtYL2 The synthetic route was as follows: [ka] (1) Synthesis of intermediate (S,R)-YL2. 2-Bpin (203 mg, 0.56 mmol, 1.0 equiv.), Ph / Im-tbu-Br (300 mg, 0.56 mmol, 1.0 equiv.), tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.02 mmol, 0.03 equiv.), and potassium carbonate (232 mg, 1.68 mmol, 3.0 equiv.) were added in this order to a dry Schlenk tube equipped with a stirrer, and the mixture was purged with nitrogen three times. Then, dioxane (6 mL) and water (1 mL) were added under nitrogen protection. The Schlenk tube was placed in an oil bath at 85 °C and the reaction was continued for 1 day with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether: ethyl acetate = 10:1 to obtain the product (S,R)-YL2, 358 mg of a white solid, with a yield of 93%. 1 H NMR(500MHz,DMSO-d6):δ(ppm) 0.90(s,9H),1.38(s,9H),1.43(s,9H),3.31-3.32(m,1H),3.52(dd,J=18.0,7.0Hz,1H),5.52-5.62(m,1H) ,5.76(d,J=8.0Hz,1H),6.90(d,J=2.5Hz,1H),7.10(dd,J=8.0,1.0Hz,1H),7.23-7.32(m,4H),7.41(t,J=8 .0Hz,1H),7.47-7.49(m,1H),7.52-7.55(m,2H),7.57(dd,J=7.5,1.0Hz,1H),7.67(t,J=8.0Hz,1H),7.71- 7.74(m,2H),7.98(dt,J=8.0,1.0Hz,1H),8.07(dt,J=8.0,1.0Hz,1H),8.59(t,J=1.5Hz,1H),13.52(s,1H).

[0087] (2) Synthesis of P-PtYL2: (S,R)-YL2 (250 mg, 0.36 mmol, 1.0 equiv.), potassium chloroplatinate (158 mg, 0.38 mmol, 1.05 equiv.), and tetrabutylammonium bromide (12 mg, 0.036 mmol, 10 mol%) were added to a dry 50 mL three-neck flask equipped with a stirrer and a condenser, in that order. The flask was then purged with nitrogen three times, and 22 mL of acetic acid (pre-bubbled with nitrogen) was added. After bubbling nitrogen through the reaction mixture for 30 minutes, the mixture was stirred at room temperature for 12 hours and then at 120 °C for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:dichloromethane=1:1 to obtain the product P-PtYL2, 211 mg of a pale yellow solid, with a yield of 66%. 1 H NMR(500MHz,DMSO-d6):δ(ppm) 0.89(s,9H),1.39(s,9H),1.56(s,9H),3.51-3.55(m,1H),3.70(dd,J=18.0,6.0Hz, 1H),5.91(d,J=6.5Hz,1H),6.16(t,J=6.5Hz,1H),7.15(d,J=8.0Hz,1H),7.18-7.23 (m,2H),7.28-7.35(m,3H),7.39(dd,J=7.0,1.0Hz,2H),7.42-7.49(m,2H),7.69-7. 82(m,3H),8.04(d,J=8.0Hz,1H),8.25(d,J=8.0Hz,1H),8.35(dd,J=8.5,1.0Hz,1H).

[0088] Example 5: Tetradentate cyclometalated platinum(II) complex M-PtYL2 The synthetic route was as follows: [ka] (1) Synthesis of intermediate (R,S)-YL2. 1-Bpin (203 mg, 0.56 mmol, 1.0 equiv.), Ph / Im-tbu-Br (300 mg, 0.56 mmol, 1.0 equiv.), tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.02 mmol, 0.03 equiv.), and potassium carbonate (232 mg, 1.68 mmol, 3.0 equiv.) were added in this order to a dry Schlenk tube equipped with a stirrer. The tube was purged with nitrogen three times, and then dioxane (6 mL) and water (1 mL) were added under nitrogen protection. The Schlenk tube was placed in an oil bath at 85 °C and stirred for 1 day. The reaction was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether: ethyl acetate = 10:1 to obtain the product (R,S)-YL2, 333 mg of a white solid, with a yield of 86%. 1 H NMR(500MHz,DMSO-d6):δ(ppm) 0.90(s,9H),1.38(s,9H),1.43(s,9H),3.31-3.32(m,1H),3.52(dd,J=18.0,7.0Hz,1H),5.52-5.58(m,1H) ,5.76(d,J=7.5Hz,1H),6.90(d,J=2.5Hz,1H),7.10(dd,J=8.0,0.5Hz,1H),7.23-7.32(m,4H),7.41(t,J=8 .0Hz,1H),7.47-7.49(m,1H),7.52-7.54(m,2H),7.57(dd,J=7.5,1.0Hz,1H),7.67(t,J=8.0Hz,1H),7.71- 7.74(m,2H),7.98(dt,J=8.0,1.0Hz,1H),8.07(dt,J=8.0,1.0Hz,1H),8.59(t,J=1.5Hz,1H),13.52(s,1H).

[0089] (2) Synthesis of M-PtYL2: (R,S)-YL2 (250 mg, 0.36 mmol, 1.0 equiv.), potassium chloroplatinate (158 mg, 0.38 mmol, 1.05 equiv.), and tetrabutylammonium bromide (12 mg, 0.036 mmol, 10 mol%) were added to a dry 50 mL three-neck flask equipped with a stirrer and a condenser, in that order. The flask was then purged with nitrogen three times, and 22 mL of acetic acid (pre-bubbled with nitrogen) was added. After bubbling nitrogen through the reaction mixture for 30 minutes, the mixture was stirred at room temperature for 12 hours and then at 120 °C for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:dichloromethane=1:1 to obtain the product M-PtYL2, 206 mg of a pale yellow solid, with a yield of 65%. 1 H NMR(500MHz,DMSO-d6):δ(ppm) 0.89(s,9H),1.39(s,9H),1.56(s,9H),3.51-3.55(m,1H),3.70(dd,J=18.0,6.0Hz, 1H),5.91(d,J=6.5Hz,1H),6.16(t,J=6.5Hz,1H),7.15(d,J=8.0Hz,1H),7.18-7.23 (m,2H),7.28-7.35(m,3H),7.39(dd,J=7.0,1.0Hz,2H),7.42-7.49(m,2H),7.69-7. 82(m,3H),8.04(d,J=8.0Hz,1H),8.25(d,J=8.0Hz,1H),8.35(dd,J=8.5,1.0Hz,1H).

[0090] Example 6: Tetradentate cyclometalated palladium(II) complex P-PdYL2 The synthetic route was as follows: [ka] To synthesize P-PdYL2, (S,R)-YL2 (300 mg, 0.44 mmol, 1.0 equiv.), palladium acetate (108 mg, 0.48 mmol, 1.1 equiv.), and tetrabutylammonium bromide (14 mg, 0.044 mmol, 10 mol%) were added, in that order, to a dry 50 mL three-neck flask equipped with a stirrer and condenser. The flask was then purged with nitrogen three times, and 26 mL of pre-purified acetic acid (26 mL) was added. After bubbling nitrogen through the reaction mixture for 30 minutes, the mixture was stirred at room temperature for 12 hours and then at 120 °C for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using a 1:1 mixture of petroleum ether and dichloromethane to obtain the product P-PdYL2 as a pale yellow solid (208 mg, 60% yield). 1 H NMR(500MHz,DMSO-d6):δ(ppm) 0.88(s,9H),1.38(s,9H),1.54(s,9H),3.50(d,J=18.0Hz,1H),3.68(dd,J=18.0,6.0Hz,1H),5 .85(d,J=7.0Hz,1H),6.01-6.12(m,1H),7.04(d,J=2.5Hz,1H),7.17(d,J=8.0Hz,1H),7.22(d,J =2.5Hz,1H),7.25(d,J=7.5Hz,1H),7.28-7.38(m,3H),7.38-7.41(m,2H),7.43(t,J=8.0Hz,1H ),7.65-7.82(m,3H),8.08(d,J=8.0Hz,1H),8.17(d,J=8.0Hz,1H),8.32(dd,J=8.0,1.0Hz,1H).

[0091] Example 7: Tetradentate cyclometalated palladium(II) complex M-PdYL2 The synthetic route was as follows: [ka] To synthesize M-PdYL2, (R,S)-YL2 (250 mg, 0.36 mmol, 1.0 equiv.), palladium acetate (90 mg, 0.40 mmol, 1.1 equiv.), and tetrabutylammonium bromide (12 mg, 0.036 mmol, 10 mol%) were added, in that order, to a dry 50 mL three-neck flask equipped with a stirrer and condenser. The flask was then purged with nitrogen three times, and 21 mL of pre-purified acetic acid (21 mL) was added. After bubbling nitrogen through the reaction mixture for 30 minutes, the mixture was stirred at room temperature for 12 hours and then at 120 °C for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using a 1:1 mixture of petroleum ether and dichloromethane to obtain 184 mg of the product M-PdYL2 as a pale yellow solid in 64% yield. 1 H NMR(500MHz,DMSO-d6):δ(ppm) 0.88(s,9H),1.38(s,9H),1.54(s,9H),3.50(d,J=18.0Hz,1H),3.68(dd,J=18.0,6.0Hz,1H),5 .85(d,J=7.0Hz,1H),6.01-6.12(m,1H),7.04(d,J=2.5Hz,1H),7.17(d,J=8.0Hz,1H),7.22(d,J =2.5Hz,1H),7.25(d,J=7.5Hz,1H),7.28-7.38(m,3H),7.38-7.41(m,2H),7.43(t,J=8.0Hz,1H ),7.65-7.82(m,3H),8.08(d,J=8.0Hz,1H),8.17(d,J=8.0Hz,1H),8.32(dd,J=8.0,1.0Hz,1H).

[0092] Example 8: Tetradentate cyclometalated platinum(II) complex P-PtYL3 The synthetic route was as follows: [ka] (1) Synthesis of intermediate (S,R)-YL3. 2-Bpin (181 mg, 0.50 mmol, 1.0 equiv.), Ph / Im-Ph-Br (249 mg, 0.50 mmol, 1.0 equiv.), tetrakis(triphenylphosphine)palladium(0) (17 mg, 0.02 mmol, 0.03 equiv.), and potassium carbonate (207 mg, 1.50 mmol, 3.0 equiv.) were added in this order to a dry Schlenk tube equipped with a stirrer, and the mixture was purged with nitrogen three times. Then, dioxane (6 mL) and water (1 mL) were added under nitrogen protection. The Schlenk tube was placed in an oil bath at 85 °C and the reaction was continued for 1 day with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:ethyl acetate=10:1 to obtain the product (S,R)-YL3 as a white solid (238 mg, 73% yield). 1 H NMR(500MHz,DMSO-d6):δ(ppm) 1.41(s,9H),3.15-3.18(m,1H),3.40(dd,J=18.0,6.5Hz,1H),5.49-5.54(m,1H),5.73(d,J=8.0Hz,1H),6. 71(t,J=8.0Hz,1H),6.92(dd,J=8.0,1.0Hz,1H),7.14(dd,J=8.0,1.0Hz,1H),7.19-7.27(m,3H),7.33(dd, J=7.5,1.5Hz,1H),7.36-7.41(m,1H),7.42-7.47(m,4H),7.55-7.60(m,5H),7.64(t,J=8.0Hz,1H),7.72-7 .74(m,2H),7.92(dt,J=8.0,1.0Hz,1H),8.11(dt,J=8.0,1.0Hz,1H),8.55(t,J=1.5Hz,1H),13.34(s,1H).

[0093] (2) Synthesis of P-PtYL3: (S,R)-YL3 (200 mg, 0.31 mmol, 1.0 equiv.), potassium chloroplatinate (134 mg, 0.32 mmol, 1.05 equiv.), and tetrabutylammonium bromide (10 mg, 0.031 mmol, 10 mol%) were added to a dry 50 mL three-neck flask equipped with a stirrer and a condenser, in that order. The flask was then purged with nitrogen three times, and acetic acid (19 mL) pre-purged with nitrogen was added. After 30 minutes of nitrogen bubbling, the reaction mixture was stirred at room temperature for 12 hours, then at 120 °C for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:dichloromethane=1:1 to obtain the product P-PtYL3, 174 mg of a pale yellow solid, with a yield of 67%. 1 H NMR(500MHz,DMSO-d6):δ(ppm) 1.43(s,9H),3.41-3.44(m,1H),3.63(dd,J=18.5,7.0Hz,1H),5.67(d,J=7.5Hz,1H),6.11-6.18(m ,1H),6.34(dd,J=8.5,7.0Hz,1H),6.82(t,J=7.5Hz,1H),6.99-7.04(m,1H),7.11-7.15(m,2H),7. 20(dd,J=8.5,1.5Hz,1H),7.22-7.28(m,3H),7.32-7.37(m,2H),7.38-7.43(m,2H),7.50(t,J=8.0 Hz,1H),7.55-7.63(m,1H),7.69-7.79(m,5H),8.29(d,J=8.0Hz,1H),8.38(dd,J=8.0,0.5Hz,1H).

[0094] Example 9: Tetradentate cyclometalated platinum(II) complex M-PtYL3 The synthetic route was as follows: [ka] (1) Synthesis of intermediate (R,S)-YL3. 1-Bpin (181 mg, 0.50 mmol, 1.0 equiv.), Ph / Im-Ph-Br (249 mg, 0.50 mmol, 1.0 equiv.), tetrakis(triphenylphosphine)palladium(0) (17 mg, 0.02 mmol, 0.03 equiv.), and potassium carbonate (207 mg, 1.50 mmol, 3.0 equiv.) were added in this order to a dry Schlenk tube equipped with a stirrer, and the mixture was purged with nitrogen three times. Then, dioxane (6 mL) and water (1 mL) were added under nitrogen protection. The Schlenk tube was placed in an oil bath at 85 °C and the reaction was continued for 1 day with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether: ethyl acetate = 10:1 to obtain the product (R,S)-YL2, 250 mg of a white solid, with a yield of 75%. 1 H NMR(500MHz,DMSO-d6):δ(ppm) 1.41(s,9H),3.15-3.18(m,1H),3.40(dd,J=18.0,6.5Hz,1H),5.49-5.54(m,1H),5.73(d,J=8.0Hz,1H),6. 71(t,J=8.0Hz,1H),6.92(dd,J=8.0,1.0Hz,1H),7.14(dd,J=8.0,1.0Hz,1H),7.19-7.27(m,3H),7.33(dd, J=7.5,1.5Hz,1H),7.36-7.41(m,1H),7.42-7.47(m,4H),7.55-7.60(m,5H),7.64(t,J=8.0Hz,1H),7.72-7 .74(m,2H),7.92(dt,J=8.0,1.0Hz,1H),8.11(dt,J=8.0,1.0Hz,1H),8.55(t,J=1.5Hz,1H),13.34(s,1H).

[0095] (2) Synthesis of M-PtYL3: (R,S)-YL3 (200 mg, 0.31 mmol, 1.0 equiv.), potassium chloroplatinate (134 mg, 0.32 mmol, 1.05 equiv.), and tetrabutylammonium bromide (10 mg, 0.031 mmol, 10 mol%) were added to a dry 50 mL three-neck flask equipped with a stirrer and a condenser, in that order. The flask was then purged with nitrogen three times, and acetic acid (19 mL) pre-bubbled with nitrogen was added. After bubbling nitrogen through the reaction mixture for 30 minutes, the mixture was stirred at room temperature for 12 hours and then at 120 °C for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:dichloromethane=1:1 to obtain the product M-PtYL3, 173 mg of a pale yellow solid, with a yield of 66%. 1 H NMR(500MHz,DMSO-d6):δ(ppm) 1.43(s,9H),3.41-3.44(m,1H),3.63(dd,J=18.5,7.0Hz,1H),5.67(d,J=7.5Hz,1H),6.11-6.18(m ,1H),6.34(dd,J=8.5,7.0Hz,1H),6.82(t,J=7.5Hz,1H),6.99-7.04(m,1H),7.11-7.15(m,2H),7. 20(dd,J=8.5,1.5Hz,1H),7.22-7.28(m,3H),7.32-7.37(m,2H),7.38-7.43(m,2H),7.50(t,J=8.0 Hz,1H),7.55-7.63(m,1H),7.69-7.79(m,5H),8.29(d,J=8.0Hz,1H),8.38(dd,J=8.0,0.5Hz,1H).

[0096] Example 10: Tetradentate cyclometalated platinum(II) complex P-PtYL4 The synthetic route was as follows: [ka] (1) Synthesis of intermediate (S,R)-YL4. 2-Bpin (115 mg, 0.32 mmol, 1.0 equiv.), Ph / Im-Nap-1-Br (150 mg, 0.32 mmol, 1.0 equiv.), tetrakis(triphenylphosphine)palladium(0) (11 mg, 0.01 mmol, 0.03 equiv.), and potassium carbonate (132 mg, 0.96 mmol, 3.0 equiv.) were added in this order to a dry Schlenk tube equipped with a stirrer. The tube was purged with nitrogen three times, and then dioxane (5 mL) and water (1 mL) were added under nitrogen protection. The Schlenk tube was placed in an oil bath at 85 °C and stirred for 1 day. The reaction was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:ethyl acetate=10:1 to obtain the product (S,R)-YL4, 79 mg of a white solid, with a yield of 40%. 1 H NMR(500MHz,DMSO-d6):δ(ppm) 1.42(s,9H),3.39-3.43(m,1H),3.56(dd,J=18.0,7.0Hz,1H),5.57-5.63(m,1H),5.79(d,J=8.0Hz,1H),6.88(d,J= 9.0Hz,1H),7.10(d,J=9.0Hz,1H),7.13(dd,J=8.0,1.0Hz,1H),7.27-7.36(m,2H),7.38(d,J=7.0Hz,1H),7.43(t,J =8.0Hz,1H),7.51(d,J=7.0Hz,1H),7.58-7.64(m,5H),7.70(t,J=8.0Hz,1H),7.72-7.76(m,2H),7.77-7.83(m,1H) ,7.99(dt,J=8.0,1.0Hz,1H),8.13(dt,J=8.0,1.0Hz,1H),8.30-8.36(m,2H),8.62(t,J=1.5Hz,1H),14.60(s,1H).

[0097] (2) Synthesis of P-PtYL4. To a dry 50 mL three-neck flask equipped with a stirrer and condenser, (S,R)-YL4 (79 mg, 0.13 mmol, 1.0 equiv.), potassium chloroplatinate (55 mg, 0.13 mmol, 1.05 equiv.), and tetrabutylammonium bromide (4 mg, 0.013 mmol, 10 mol%) were added in this order. The flask was then purged with nitrogen three times, and acetic acid (10 mL) pre-purged with nitrogen was added. After bubbling nitrogen through the reaction mixture for 30 min, the mixture was stirred at room temperature for 12 h and then at 120 °C for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using a 1:1 mixture of petroleum ether and dichloromethane to obtain the product P-PtYL4 as a pale yellow solid (55 mg, 53% yield). 1 H NMR(500MHz,CDCl3):δ(ppm) 1.46(s,9H),3.66-3.75(m,2H),6.02-6.05(m,1H),6.21(d,J=7.5Hz,1H),6.69(d,J=9.0H z,1H),7.13-7.19(m,2H),7.22(d,J=9.0Hz,1H),7.26-7.28(m,2H),7.31(d,J=7.5Hz,1H) ,7.33-7.40(m,4H),7.45-7.47(m,1H),7.50-7.52(m,1H),7.63(dd,J=17.0,8.0Hz,3H),8 .13(d,J=8.0Hz,1H),8.27(d,J=8.0Hz,1H),8.51(d,J=8.0Hz,1H),8.99(d,J=8.0Hz,1H).

[0098] Example 11: Tetradentate cyclometalated platinum(II) complex M-PtYL4 The synthetic route was as follows: [ka] (1) Synthesis of intermediate (R,S)-YL4. 1-Bpin (115 mg, 0.32 mmol, 1.0 equiv.), Ph / Im-Nap-1-Br (150 mg, 0.32 mmol, 1.0 equiv.), tetrakis(triphenylphosphine)palladium(0) (11 mg, 0.01 mmol, 0.03 equiv.), and potassium carbonate (132 mg, 0.96 mmol, 3.0 equiv.) were added in this order to a dry Schlenk tube equipped with a stirrer. The tube was purged with nitrogen three times, and then dioxane (5 mL) and water (1 mL) were added under nitrogen protection. The Schlenk tube was placed in an oil bath at 85 °C and stirred for 1 day. The reaction was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:ethyl acetate=10:1 to obtain the product (S,R)-YL4, 100 mg of a white solid, with a yield of 50%. 1 H NMR(500MHz,DMSO-d6):δ(ppm) 1.42(s,9H),3.39-3.43(m,1H),3.56(dd,J=18.0,7.0Hz,1H),5.57-5.63(m,1H),5.79(d,J=8.0Hz,1H),6.88(d,J= 9.0Hz,1H),7.10(d,J=9.0Hz,1H),7.13(dd,J=8.0,1.0Hz,1H),7.27-7.36(m,2H),7.38(d,J=7.0Hz,1H),7.43(t,J =8.0Hz,1H),7.51(d,J=7.0Hz,1H),7.58-7.64(m,5H),7.70(t,J=8.0Hz,1H),7.72-7.76(m,2H),7.77-7.83(m,1H) ,7.99(dt,J=8.0,1.0Hz,1H),8.13(dt,J=8.0,1.0Hz,1H),8.30-8.36(m,2H),8.62(t,J=1.5Hz,1H),14.60(s,1H).

[0099] (2) Synthesis of M-PtYL4. To a dry 50 mL three-neck flask equipped with a stirrer and condenser, (R,S)-YL4 (90 mg, 0.14 mmol, 1.0 equiv.), potassium chloroplatinate (63 mg, 0.15 mmol, 1.05 equiv.), and tetrabutylammonium bromide (5 mg, 0.014 mmol, 10 mol%) were added in this order. The flask was then purged with nitrogen three times, and acetic acid (10 mL) pre-purged with nitrogen was added. After bubbling nitrogen through the reaction mixture for 30 min, the mixture was stirred at room temperature for 12 h and then at 120 °C for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The crude product was purified by silica gel column chromatography using a 1:1 mixture of petroleum ether and dichloromethane to obtain the product M-PtYL4, 64 mg of a pale yellow solid, in 54% yield. 1 H NMR(500MHz,CDCl3):δ(ppm) 1.46(s,9H),3.66-3.75(m,2H),6.02-6.05(m,1H),6.21(d,J=7.5Hz,1H),6.69(d,J=9.0H z,1H),7.13-7.19(m,2H),7.22(d,J=9.0Hz,1H),7.26-7.28(m,2H),7.31(d,J=7.5Hz,1H) ,7.33-7.40(m,4H),7.45-7.47(m,1H),7.50-7.52(m,1H),7.63(dd,J=17.0,8.0Hz,3H),8 .13(d,J=8.0Hz,1H),8.27(d,J=8.0Hz,1H),8.51(d,J=8.0Hz,1H),8.99(d,J=8.0Hz,1H).

[0100] Example 12: Tetradentate cyclometalated platinum(II) complex P-PtYL5 The synthetic route was as follows: [ka] (1) Synthesis of intermediate (S,R)-YL5. 2-Bpin (184 mg, 0.51 mmol, 1.0 equiv.), Ph / Im-Nap-2-Br (240 mg, 0.51 mmol, 1.0 equiv.), tetrakis(triphenylphosphine)palladium(0) (18 mg, 0.015 mmol, 0.03 equiv.), and potassium carbonate (211 mg, 1.53 mmol, 3.0 equiv.) were added in this order to a dry Schlenk tube equipped with a stirrer. The tube was purged with nitrogen three times, and then dioxane (5 mL) and water (1 mL) were added under nitrogen protection. The Schlenk tube was placed in an oil bath at 85 °C and stirred for 1 day. The reaction was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:ethyl acetate=10:1 to obtain the product (S,R)-YL5 as a white solid (204 mg) with a yield of 64%. 1 H NMR(500MHz,CDCl3):δ(ppm) 1.19(s,9H),3.44-3.56(m,2H),5.51-5.55(m,1H),5.78(d,J=8.0Hz,1H),6.90-6.95(m,1H),7.05 (t,J=7.5Hz,3H),7.19(d,J=8.0Hz,2H),7.24-7.25(m,2H),7.27-7.29(m,2H),7.34(d,J=8.5Hz,1 H),7.40(t,J=8.0Hz,1H),7.50(d,J=8.0Hz,1H),7.53(t,J=8.0Hz,1H),7.56-7.60(m,3H),7.76(d ,J=9.0Hz,1H),7.98(d,J=8.0Hz,1H),8.27(d,J=8.0Hz,1H),8.52(t,J=1.5Hz,1H),10.61(s,1H).

[0101] (2) Synthesis of P-PtYL5: (S,R)-YL5 (170 mg, 0.27 mmol, 1.0 equiv.), potassium chloroplatinate (118 mg, 0.29 mmol, 1.05 equiv.), and tetrabutylammonium bromide (9 mg, 0.027 mmol, 10 mol%) were added to a dry 50 mL three-neck flask equipped with a stirrer and a condenser, in that order. The flask was then purged with nitrogen three times, and 17 mL of acetic acid (pre-bubbled with nitrogen) was added. After bubbling nitrogen through the reaction mixture for 30 minutes, the mixture was stirred at room temperature for 12 hours and then at 120 °C for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:dichloromethane=1:1 to obtain the product P-PtYL5, 130 mg of a pale yellow solid, with a yield of 61%. 1 H NMR(500MHz,DMSO-d6):δ(ppm) 1.18(s,9H),1.19(s,9H),3.51(d,J=5.0Hz,1H),3.54(d,J=5.0Hz,1H),3.69(t,J=6.5Hz,1H),3.72(t,J=6.5Hz,1H), 5.92(d,J=8.0Hz,1H),5.96(d,J=7.5Hz,1H),6.15-6.21(m,2H),6.75-6.83(m,2H),6.85-6.93(m,2H),7.06-7.34(m,9 H),7.34-7.42(m,9H),7.44-7.46(m,2H),7.49-7.56(m,6H),7.62(t,J=7.0Hz,2H),7.82(d,J=9.0Hz,1H),7.87(d,J= 9.0Hz,1H),8.15(d,J=8.0Hz,1H),8.26(d,J=8.0Hz,1H),8.29(d,J=8.0Hz,1H),8.36-8.40(m,2H),8.45-8.49(m,1H).

[0102] Example 13: Tetradentate cyclometalated platinum(II) complex M-PtYL5 The synthetic route was as follows: [ka] (1) Synthesis of intermediate (R,S)-YL5. 1-Bpin (184 mg, 0.51 mmol, 1.0 equiv.), Ph / Im-Nap-2-Br (240 mg, 0.51 mmol, 1.0 equiv.), tetrakis(triphenylphosphine)palladium(0) (18 mg, 0.015 mmol, 0.03 equiv.), and potassium carbonate (211 mg, 1.53 mmol, 3.0 equiv.) were added in this order to a dry Schlenk tube equipped with a stirrer. The tube was purged with nitrogen three times, and then dioxane (5 mL) and water (1 mL) were added under nitrogen protection. The Schlenk tube was placed in an oil bath at 85 °C and stirred for 1 day. The reaction was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether: ethyl acetate = 10:1 to obtain the product (S,R)-YL5, 190 mg of a white solid, with a yield of 60%. 1 H NMR(500MHz,CDCl3):δ(ppm) 1.19(s,9H),3.44-3.56(m,2H),5.51-5.55(m,1H),5.78(d,J=8.0Hz,1H),6.90-6.95(m,1H),7.05 (t,J=7.5Hz,3H),7.19(d,J=8.0Hz,2H),7.24-7.25(m,2H),7.27-7.29(m,2H),7.34(d,J=8.5Hz,1 H),7.40(t,J=8.0Hz,1H),7.50(d,J=8.0Hz,1H),7.53(t,J=8.0Hz,1H),7.56-7.60(m,3H),7.76(d ,J=9.0Hz,1H),7.98(d,J=8.0Hz,1H),8.27(d,J=8.0Hz,1H),8.52(t,J=1.5Hz,1H),10.61(s,1H).

[0103] (2) Synthesis of M-PtYL5: (R,S)-YL5 (161 mg, 0.26 mmol, 1.0 equiv.), potassium chloroplatinate (112 mg, 0.27 mmol, 1.05 equiv.), and tetrabutylammonium bromide (8 mg, 0.026 mmol, 10 mol%) were added in this order to a dry 50 mL three-neck flask equipped with a stirrer and a condenser. The flask was then purged with nitrogen three times, and 16 mL of acetic acid (pre-bubbled with nitrogen) was added. After bubbling nitrogen through the reaction mixture for 30 minutes, the mixture was stirred at room temperature for 12 hours and then at 120 °C for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:dichloromethane=1:1 to obtain the product M-PtYL5, 120 mg of a pale yellow solid, with a yield of 57%. 1 H NMR(500MHz,DMSO-d6):δ(ppm) 1.18(s,9H),1.19(s,9H),3.51(d,J=5.0Hz,1H),3.54(d,J=5.0Hz,1H),3.69(t,J=6.5Hz,1H),3.72(t,J=6.5Hz,1H), 5.92(d,J=8.0Hz,1H),5.96(d,J=7.5Hz,1H),6.15-6.21(m,2H),6.75-6.83(m,2H),6.85-6.93(m,2H),7.06-7.34(m,9 H),7.34-7.42(m,9H),7.44-7.46(m,2H),7.49-7.56(m,6H),7.62(t,J=7.0Hz,2H),7.82(d,J=9.0Hz,1H),7.87(d,J= 9.0Hz,1H),8.15(d,J=8.0Hz,1H),8.26(d,J=8.0Hz,1H),8.29(d,J=8.0Hz,1H),8.36-8.40(m,2H),8.45-8.49(m,1H).

[0104] Example 14: Tetradentate cyclometalated platinum(II) complex P-PtYL6 The synthetic route was as follows: [ka] (1) Synthesis of intermediate (S,R)-YL6. 2-Bpin (142 mg, 0.39 mmol, 1.0 equiv.), Ph / Im-Cz-Br (250 mg, 0.41 mmol, 1.0 equiv.), tetrakis(triphenylphosphine)palladium(0) (14 mg, 0.012 mmol, 0.03 equiv.), and potassium carbonate (163 mg, 1.18 mmol, 3.0 equiv.) were added in this order to a dry Schlenk tube equipped with a stirrer. The tube was purged with nitrogen three times, and then dioxane (4 mL) and water (1 mL) were added under nitrogen protection. The Schlenk tube was placed in an oil bath at 85 °C and stirred for 1 day. The reaction was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether: ethyl acetate = 10:1 to obtain the product (S,R)-YL6 as a white solid (255 mg) with a yield of 86%. 1 H NMR(500MHz,CDCl3):δ(ppm) 1.11(s,9H),1.44(s,9H),1.46(s,9H),3.26-3.33(m,1H),3.41(dd,J=18.0,7.0Hz,1H),5.47-5.50(m,1H), 5.82(d,J=8.0Hz,1H),7.17(dd,J=8.0,1.0Hz,1H),7.20(d,J=2.0Hz,1H),7.20-7.24(m,1H),7.26-7.28(m,2 H),7.31-7.36(m,2H),7.42-7.48(m,3H),7.54(dd,J=7.5,1.0Hz,1H),7.57-7.60(m,1H),7.62(t,J=8.0Hz, 1H),7.65-7.68(m,2H),8.05-8.11(m,3H),8.30(dt,J=8.0,1.5Hz,1H),8.84(t,J=1.5Hz,1H),11.17(s,1H).

[0105] (2) Synthesis of P-PtYL6: (S,R)-YL6 (200 mg, 0.26 mmol, 1.0 equiv.), potassium chloroplatinate (115 mg, 0.28 mmol, 1.05 equiv.), and tetrabutylammonium bromide (9 mg, 0.026 mmol, 10 mol%) were added to a dry 50 mL three-neck flask equipped with a stirrer and a condenser, in that order. The flask was then purged with nitrogen three times, and 16 mL of acetic acid (pre-purged with nitrogen) was added. After 30 minutes of nitrogen bubbling, the reaction mixture was stirred at room temperature for 12 hours and then at 120 °C for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:dichloromethane=1:1 to obtain the product P-PtYL6, 157 mg of a pale yellow solid, with a yield of 63%. 1 H NMR(500MHz,CDCl3):δ(ppm) 1.14(s,9H),1.43(s,9H),1.44(s,9H),3.45-3.53(m,2H),5.89-5.92(m,1H),6.32(d,J=8.0Hz,1H),6.43(d, J=7.0Hz,1H),6.69(t,J=7.5Hz,1H),6.93-7.01(m,2H),7.05(d,J=8.0Hz,1H),7.08(d,J=7.5Hz,1H),7.33(t ,J=7.5Hz,1H),7.37(t,J=8.0Hz,1H),7.43(dd,J=8.5,2.0Hz,1H),7.47(d,J=2.0Hz,1H),7.48-7.53(m,2H), 7.77-7.84(m,3H),8.12(d,J=2.0Hz,1H),8.14(d,J=8.0Hz,1H),8.31(d,J=2.0Hz,1H),8.33(d,J=8.0Hz,1H).

[0106] Example 15: Tetradentate cyclometalated platinum(II) complex M-PtYL6 The synthetic route was as follows: [ka] (1) Synthesis of intermediate (R,S)-YL6. 1-Bpin (147 mg, 0.41 mmol, 1.0 equiv.), Ph / Im-Cz-Br (300 mg, 0.41 mmol, 1.0 equiv.), tetrakis(triphenylphosphine)palladium(0) (14 mg, 0.012 mmol, 0.03 equiv.), and potassium carbonate (169 mg, 1.22 mmol, 3.0 equiv.) were added in this order to a dry Schlenk tube equipped with a stirrer. The tube was purged with nitrogen three times, and then dioxane (4 mL) and water (1 mL) were added under nitrogen protection. The Schlenk tube was placed in an oil bath at 85 °C and stirred for 1 day. The reaction was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:ethyl acetate=10:1 to obtain the product (S,R)-YL6 as a white solid (298 mg, 80% yield). 1 H NMR(500MHz,CDCl3):δ(ppm) 1.11(s,9H),1.44(s,9H),1.46(s,9H),3.26-3.33(m,1H),3.41(dd,J=18.0,7.0Hz,1H),5.47-5.50(m,1H), 5.82(d,J=8.0Hz,1H),7.17(dd,J=8.0,1.0Hz,1H),7.20(d,J=2.0Hz,1H),7.20-7.24(m,1H),7.26-7.28(m,2 H),7.31-7.36(m,2H),7.42-7.48(m,3H),7.54(dd,J=7.5,1.0Hz,1H),7.57-7.60(m,1H),7.62(t,J=8.0Hz, 1H),7.65-7.68(m,2H),8.05-8.11(m,3H),8.30(dt,J=8.0,1.5Hz,1H),8.84(t,J=1.5Hz,1H),11.17(s,1H).

[0107] (2) Synthesis of M-PtYL6: (R,S)-YL6 (180 mg, 0.24 mmol, 1.0 equiv.), potassium chloroplatinate (103 mg, 0.25 mmol, 1.05 equiv.), and tetrabutylammonium bromide (8 mg, 0.024 mmol, 10 mol%) were added to a dry 50 mL three-neck flask equipped with a stirrer and a condenser, in that order. The flask was then purged with nitrogen three times, and 15 mL of acetic acid (pre-bubbled with nitrogen) was added. After bubbling nitrogen through the reaction mixture for 30 minutes, the mixture was stirred at room temperature for 12 hours and then at 120 °C for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:dichloromethane=1:1 to obtain the product M-PtYL6, 120 mg of a pale yellow solid, with a yield of 52%. 1 H NMR(500MHz,DMSO-d6):δ(ppm) 1.11(s,9H),1.40(s,9H),1.42(s,9H),3.41-3.43(m,1H),3.54(dd,J=18.0,6.5Hz,1H),6.11(t,J=6.5Hz,1H),6.16(d,J=8.0Hz,1 H),6.28(d,J=7.0Hz,1H),6.61(t,J=8.0Hz,1H),7.01(t,J=7.5Hz,1H),7.04(d,J=8.0Hz,1H),7.14(dd,J=8.0,2.5Hz,1H),7.19(d, J=7.5Hz,1H),7.39(t,J=7.5Hz,1H),7.43-7.52(m,4H),7.64(dd,J=8.5,2.5Hz,1H),7.78(d,J=8.5Hz,1H),7.94(dd,J=8.0,2.5Hz ,1H),8.05(dd,J=8.0,2.5Hz,1H),8.23(d,J=2.0Hz,1H),8.33(d,J=8.0Hz,1H),8.44(d,J=2.0Hz,1H),8.47(dd,J=8.0,0.5Hz,1H).

[0108] Example 16: Tetradentate cyclometalated platinum(II) complex P-PtYL35 The synthetic route was as follows: [ka] (1) Synthesis of intermediate (S,R)-YL35. 2-Bpin (2.08 g, 5.76 mmol, 1.0 equiv.), Ph / Im-Nap-3-Br (3.15 mg, 5.76 mmol, 1.0 equiv.), tetrakis(triphenylphosphine)palladium(0) (200 mg, 0.17 mmol, 0.03 equiv.), and potassium carbonate (2.39 mg, 17.30 mmol, 3.0 equiv.) were added to a dry 100 mL three-neck flask equipped with a stirrer, in that order, and purged with nitrogen three times. Then, dioxane (30 mL) and water (6 mL) were added under nitrogen protection. The three-neck flask was placed in an oil bath at 85 °C and stirred for 1 day. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:ethyl acetate=10:1 to obtain the product (S,R)-YL35, 3.90 g of a white solid, with a yield of 97%. 1 H NMR(500MHz,DMSO-d6):δ(ppm) 1.43(s,9H),3.36(d,J=5.0Hz,1H),3.48-3.57(m,1H),5.53-5.59(m,1H),5.76(d,J=8.5Hz,1H),6.84-6.88 (m,2H),6.93-6.98(m,3H),7.03(t,J=7.5Hz,2H),7.09(d,J=9.0Hz,1H),7.26-7.36(m,4H),7.50(t,J=6.5H z,2H),7.57(dd,J=6.5,3.0Hz,2H),7.61-7.68(m,3H),7.72(dd,J=8.5,2.0Hz,1H),7.77(dd,J=6.0,3.0Hz, 1H),7.92-7.98(m,1H),8.04(d,J=8.0Hz,1H),8.26(dd,J=6.0,3.5Hz,1H),8.54-8.57(m,1H),14.62(s,1H).

[0109] (2) Synthesis of P-PtYL35: (S,R)-YL35 (4.98 g, 7.1 mmol, 1.0 equiv.), potassium chloroplatinate (3.09 g, 7.4 mmol, 1.05 equiv.), and tetrabutylammonium bromide (0.29 g, 0.71 mmol, 10 mol%) were added to a dry 1000 mL three-neck flask equipped with a stirrer and a condenser, in that order. The flask was then purged with nitrogen three times, and acetic acid (426 mL) pre-purged with nitrogen was added. After 60 minutes of nitrogen bubbling, the reaction mixture was stirred at room temperature for 12 hours and then at 120 °C for 2 days with stirring. The mixture was then cooled to room temperature, and the solvent was removed by distillation under reduced pressure. The obtained crude product was purified by silica gel column chromatography, and the eluent was petroleum ether:dichloromethane=1:1 to obtain the product P-PtYL35, 4.57 g of a pale yellow solid, with a yield of 72%. 1 H NMR(500MHz,CDCl3):δ(ppm) 1.51(s,9H),3.62-3.73(m,2H),6.02(td,J=6.5,5.5,1.5Hz,1H),6.19(d,J=7.5Hz,1H),6.75(d,J=9.5Hz, 1H),6.89(d,J=8.0Hz,1H),6.98-7.05(m,3H),7.11-7.17(m,3H),7.24(d,J=8.0Hz,1H),7.25-7.26(m,1H) ,7.29(d,J=7.5Hz,1H),7.32-7.38(m,2H),7.42-7.49(m,3H),7.50-7.54(m,1H),7.59-7.64(m,2H),7.71( d,J=2.0Hz,1H),8.02(d,J=8.0Hz,1H),8.22(d,J=7.5Hz,1H),8.45(d,J=7.5Hz,1H),8.96(d,J=8.5Hz,1H).

[0110] (Explanation of electrochemistry, optical properties tests and theoretical calculations) Absorption spectra were measured at room temperature on an Agilent 8453 UV-Vis spectrometer, with steady-state emission and lifetime measurements performed on a Horiba Jobin Yvon FluoroLog-3 spectrometer, or on a Shimadzu RF-6000 spectrometer. Low-temperature (77 K) emission spectra and lifetimes were measured in liquid nitrogen-cooled 2-methyltetrahydrofuran (2-MeTHF) solutions. Theoretical calculations for the Pt(II) complexes were performed using the software package Gaussian 09. Density functional theory (DFT) was used to optimize the ground-state (S0) molecular geometry. DFT calculations were performed using the B3LYP functional, with the 6-31G(d) basis set for C, H, O, and N atoms and the LANL2DZ basis set for Pt and Pd atoms. Measurement of circular dichroism spectra (CD) and circular polarization tests were carried out using spectrophotometers JASCO J-815 and JASCO CPL-300 manufactured by JASCO Corporation, respectively, and the test conditions were both dichloromethane solutions at room temperature.

[0111] (Experimental data and analysis) Figure 1 shows the design concept of a circularly polarized luminescent material based on a spiro-chiral tetradentate cyclometallate complex centered on an optically pure metal ion. Optically pure raw materials are economical and readily available, and the central chirality spontaneously induces the generation of spiro-chirality. The circularly polarized luminescent material does not require chiral resolution, significantly reducing the production costs of optically pure materials and enabling mass production without the limitation of separation by chiral preparative column chromatography.

[0112] As can be seen from the molecular structure of a tetradentate cyclometalated platinum(II) complex optimized by density functional theory (DFT) calculations (Figure 2), a ligand with central chirality (R,S) can spontaneously induce the generation of M-type spiro chirality, and a ligand with central chirality (S,R) can spontaneously induce the generation of P-type spiro chirality, and the M-type spiro chiral molecules and P-type spiro chiral molecules are enantiomers of each other. Furthermore, the molecular structures of the tetradentate cyclometalated palladium(II) complexes optimized by DFT calculations were similar.

[0113] As can be seen from the room-temperature emission spectra of the synthesized optically pure spiro-chiral material molecules in dichloromethane solution in Figures 3 to 9, the emission color of the cyclometallate complex can be efficiently tuned by adjusting the structure of the tetradentate ligand, from the green light region at approximately 470 nm to the yellow light region at 570 nm. Furthermore, the almost complete overlap of the emission spectra in Figures 3 to 9 further proves that the corresponding material molecules in the figures are enantiomers.

[0114] Figures 10 to 18 show schematic diagrams of the HOMO and LUMO orbital distributions of compounds P-PtYL1, P-PtYL2, and P-PtYL3 to P-PtYL34. As can be seen from the results of density functional theory (DFT) calculations (Table 3), compounds such as Pt-4, Pt-5, Pt-16, and Pt-17 have nearly identical HOMO orbital distributions. The HOMO orbital distribution is primarily concentrated in the phenyl group bonded to the phenolic oxygen and the deprotonated carbazolyl group. Alkyl group substitution has a relatively minor effect on the HOMO orbital distribution. Furthermore, aryl and heteroaryl groups cause electron delocalization, lowering the HOMO energy level and increasing the energy gap, resulting in a blue shift in the emission of the metal complexes. The LUMO orbital distribution of Pt-18, Pt-20, Pt-28, and Pt-30 is primarily concentrated in the phenyl group para to the phenolic oxygen. Introducing alkyl, aryl, or heteroatoms into this position can effectively adjust the LUMO energy level and tailor the optical properties of the luminescent material. As can be seen from the dihedral angle trends in Table 3, the rigidity of the chiral segment is a major factor in determining the size of the dihedral angle, which in turn affects the response value, or g value, of the spiro-chiral complex.

[0115] 19 to 24 show circular dichroism spectra of compounds (S,R)-P-PtYL1 and (R,S)-M-PtYL1, (S,R)-P-PtYL2 and (R,S)-M-PtYL2, (S,R)-P-PtYL3 and (R,S)-M-PtYL3, (S,R)-P-PtYL4 and (R,S)-M-PtYL4, (S,R)-P-PtYL5 and (R,S)-M-PtYL5, (S,R)-P-PtYL6 and (R,S)-M-PtYL6 in dichloromethane solution, where CD is the circular dichroism spectrum and the sample concentration is 5×10 -5 M, and its spectrum has a very high mirror symmetry. In addition, there is a very strong Cotton effect at approximately 380, 390, and 400. This indicates that other enantiomers, such as the enantiomers (S,R)-P-PtYL1 and (R,S)-M-PtYL1, all have a very strong polarizing ability for linearly polarized light.

[0116] The chemical and thermal stability of the material is high. The tetradentate ligand designed and developed is dsp 2 It can coordinate well with the hybrid platinum(II) and palladium(II) metal ions to form a stable and rigid square-structure molecule, and its chemical stability is high. Furthermore, the designed central chiral ligand L a and another terminal ligand L 1 or L b There is a large steric hindrance effect between the metal complex and the chiral tetradentate cyclometallate complex, and the entire metal complex molecule can form a stable spiro-chiral tetradentate cyclometallate complex, which does not lose its circularly polarized luminescence property due to racemization either in solution or during high-temperature sublimation.

[0117] As can be seen from the specific rotation data of some chiral starting intermediates and chiral metal complexes in Table 1 below, the direction of rotation of starting intermediates and chiral metal complexes with the same central chirality is completely different, and the specific rotation values ​​also differ significantly. This indicates that the spiro chirality of a metal ion-centered complex has a decisive impact on the optical rotation properties of the entire compound. Furthermore, complexes with the same central chirality and spiro chirality, but with different ligand structures, also show large differences in specific rotation, such as (S,R)-P-PtYL1 (+696.7) and (S,R)-P-PtYL1 (-730.0), indicating that the ligand structure has a significant impact on the optical rotation. Furthermore, since the radiative emission of excited metal complexes is primarily related to metal-to-ligand charge transfer (MLCT) and intraligand charge transfer (ILCT), the spiro chirality and ligand structure of a metal complex also have a significant impact on its circular polarization properties. Since the enantiomeric purity is all higher than 99%, this series of spiro-chirality tetradentate cyclometallate complex circularly polarized luminescent materials has very high isomeric purity, and the steric hindrance of the central chirality-induced spiro-chirality segment is sufficiently large, which ensures that the platinum complex does not racemize and has a stable configuration.

[0118] As can be seen from Table 2 below, one part with P-PtYL2 as the emitting material has a significant circularly polarized photoluminescence signal, and the asymmetry factor (g PL ) is 1.43 × 10 -3 This indicates that the series of spiro-chirality tetradentate cyclometallate complex circularly polarized luminescent materials have good prospects for application. [ka] JPEG2025528613000056.jpg1987JPEG2025528613000057.jpg7587JPEG2025528613000058.jpg5290 JPEG2025528613000059.jpg2087JPEG2025528613000060.jpg9577JPEG2025528613000061.jpg6481 [ka] JPEG2025528613000063.jpg92106

[0119] In organic light-emitting devices, when carriers are injected from the positive and negative electrodes into the light-emitting material, the light-emitting material enters an excited state and emits light. The complex of the present invention, represented by general formula (1), may be used as a phosphorescent material in excellent organic light-emitting devices such as organic photoluminescence devices or organic electroluminescence devices. Organic photoluminescence devices have a structure in which at least an emitting layer is formed on a substrate. Organic electroluminescence devices have a structure in which at least an anode, a cathode, and an organic layer formed between the anode and the cathode are included. The organic layer includes at least an emitting layer, and may be composed solely of an emitting layer, or may include one or more organic layers in addition to the emitting layer. Examples of such other organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. The hole transport layer may be a hole injection transport layer with hole injection function, and the electron transport layer may be an electron injection transport layer with electron injection function. A schematic diagram of a specific organic light-emitting device structure is shown in Figure 32. In Figure 32, 110 represents the substrate, 120 represents the anode, 130 represents the hole injection layer, 140 represents the hole transport layer, 150 represents the light-emitting layer, 160 represents the hole blocking layer, 170 represents the electron transport layer, 180 represents the electron injection layer, and 190 represents the cathode, of which the light-emitting layer is a mixed layer in which a guest material is doped into a host material.

[0120] Each layer of the organic light-emitting component of the present invention may be formed by a vacuum deposition method, a sputtering method, an ion plating method, or a wet film formation method such as a spin coating method, a printing method, or a printing method, and the solvent used is not particularly limited.

[0121] In a preferred embodiment of the present invention, the OLED component of the present invention contains a hole transport layer, and the hole transport material may be preferably selected from known or unknown materials, and is particularly preferably selected from the following structures, although the present invention is not limited to the following structures: [ka] JPEG2025528613000065.jpg137106JPEG2025528613000066.jpg138106JPEG2025528613000067.jpg148106

[0122] In a preferred embodiment of the present invention, the hole transport layer contained in the OLED component of the present invention comprises one or more p-type dopants, which in the present invention preferably have the following structure, although the present invention is not limited to the following structure: [ka]

[0123] In a preferred embodiment of the present invention, the electron transport layer may be at least one selected from compounds ET-1 to ET-77, although the present invention is not limited to the following structures. [ka] JPEG2025528613000070.jpg150106JPEG2025528613000071.jpg77106

[0124] The electron transport layer may be formed from an organic material with one or more n-type dopants (eg, LiQ, LiTHPh, etc.).

[0125] [ka] When the compounds shown in the examples are used as circularly polarized light-emitting materials in OLED components, their structure can be represented as follows: on glass containing ITO, the hole injection layer (HIL) is HT-1:P-3 (95:5 v / v%) and has a thickness of 10 nm, the hole transport layer (HTL) is HT-1 and has a thickness of 90 nm, the electron blocking layer (EBL) is HT-10 and has a thickness of 10 nm, the light-emitting layer (EML) is a host material (H-1 or H-2 or H-3 or H-4 or H-5 or H-6): the platinum metal complex of the present invention (95:5 v / v%) and has a thickness of 35 nm, the electron transport layer (ETL) is ET-13:LiQ (50:50 v / v%) and has a thickness of 35 nm, and then a 70 nm thick evaporated cathode Al. [ka]

[0126] As can be seen from Table 3 below, all of the OLED components doped with the spiro-chirality metal complexes of the present application can exhibit strong circularly polarized luminescence signals, revealing great potential for use in the field of circularly polarized luminescence. JPEG2025528613000074.jpg5176

[0127] It should be noted that the above structure is merely one example of the use of the circularly polarized luminescent material of the present invention, and does not constitute a specific limitation on the structure of OLED components made from the circularly polarized luminescent material disclosed in the present invention, nor is the circularly polarized luminescent material limited to the compounds disclosed in the examples.

[0128] It should be understood by those skilled in the art that the above-described embodiments are specific examples for realizing the present invention, and that various changes in form and details may be made in actual applications without departing from the spirit and scope of the present invention. For example, many of the substituent structures described herein may be replaced with other structures without departing from the spirit of the present invention.

Claims

1. The chemical formulas are as shown in general formulas (1), (1'), (2), and (2'), where (1) and (1'), and (2) and (2') are enantiomers of each other. 【Chemical 1】 or 【Chemistry 2】 In the formula, M is Pt or Pd, and V １ , V ２ , V ３ are each independently N or C; L ａ is a five-membered central chiral carbocyclic or heterocyclic ring; X is O, S, CR ｘ R ｙ , C=O, SiR ｘ R ｙ , GeR ｘ R ｙ , NR ｚ , PR ｚ , R ｚ , P=O, AsR ｚ , R ｚ , As=O, S=O, SO ２ , Se, Se=O, SeO ２ , BH, BR ｚ , R ｚ , Bi=O or BiR ｚ and Y is O, S; Z １ , Z ２ , Z ３ , Z ４ , Z ５ , Z ６ , Z ７ , Z ８ , Z ９ , Z １０ , Z １１ , Z １２ , Z １３ are each independently N or C; R １ , R ２ , R ３ , R ４ , R ａ , R ｂ , R ｃ , R ｄ each independently represents mono-, di-, tri-, or tetra-substituted or unsubstituted, and R １ , R ２ , R ３ , R ４ , R ａ , R ｂ , R ｃ , R ｄ are each independently hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, aryl group, heteroalkyl group, heterocycloalkyl group, heteroaryl group, haloalkyl group, haloaryl group, haloheteroaryl group, alkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxy group, mercapto group, nitro group, cyano group, amino group, mono- or di-alkylamino group, mono- or diarylamino group, ester group, nitrile group, isonitrile group, heteroaryl group, alkoxycarbonyl group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, sulfinyl group, carbamide group, phosphoramide group, imine group, sulfo group, carboxy group, hydrazino group, substituted silyl group, or a combination thereof; ａ and R ｂ are different substituents in the same molecule, and two or more adjacent R １ , R ２ , R ３ and R ４ may optionally be bonded to form a fused ring, and R ａ , R ｂ , R ｃ and R ｄ and a circularly polarized luminescent material comprising a central chirality-induced spirochiral tetradentate cyclometallated platinum(II) and palladium(II) complex, characterized in that any two of the functional groups may be bonded to form a ring system.

2. The circularly polarized luminescent material is a central chirality-induced spiro-chirality tetradentate cyclometalated platinum(II) and palladium(II) complex circularly polarized luminescent material having the general formula (1), (1'), (2), or (2') according to claim 1, and preferably has the following general formula (1-A) or (2-A) and its enantiomer (1'-A) or (2'-A): 【Chemistry 3】 Or, 【Chemistry 4】 wherein M is Pt or Pd; L ａ is a five-membered central chiral carbocyclic or heterocyclic ring; X is O, S, CR ｘ R ｙ , C=O, SiR ｘ R ｙ , GeR ｘ R ｙ , NR ｚ , PR ｚ , R ｚ , P=O, AsR ｚ , R ｚ , As=O, S=O, SO ２ , Se, Se=O, SeO ２ , BH, BR ｚ , R ｚ , Bi=O or BiR ｚ and Y is O, S; Z １ , Z ２ , Z ３ , Z ４ , Z ５ , Z ６ , Z ７ , Z ８ , Z ９ , Z １０ , Z １１ , Z １２ , Z １３ are each independently N or C; R １ , R ２ , R ３ , R ４ , R ａ , R ｂ , R ｃ , R ｄ each independently represents mono-, di-, tri-, or tetra-substituted or unsubstituted, and R １ , R ２ , R ３ , R ４ , R ａ , R ｂ , R ｃ , R ｄ are each independently hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, aryl group, heteroalkyl group, heterocycloalkyl group, heteroaryl group, haloalkyl group, haloaryl group, haloheteroaryl group, alkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxy group, mercapto group, nitro group, cyano group, amino group, mono- or di-alkylamino group, mono- or diarylamino group, ester group, nitrile group, isonitrile group, heteroaryl group, alkoxycarbonyl group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, sulfinyl group, carbamide group, phosphoramide group, imine group, sulfo group, carboxy group, hydrazino group, substituted silyl group, or a combination thereof; ａ and R ｂ are different substituents in the same molecule, and two or more adjacent R １ , R ２ , R ３ and R ４ may optionally be bonded to form a fused ring, and R ａ , R ｂ , R ｃ and R ｄ Circularly polarized light-emitting materials are spiro-chiral tetradentate cyclometallated platinum(II) and palladium(II) complexes, in which any two of the functional groups may be bonded to form a ring system.

3. The spiro-chirality tetradentate cyclometalated platinum (II) and palladium (II) complex circularly polarized luminescent material according to claim 1 or 2, wherein the central chirality segment L ａ is preferably selected from, but not limited to, the following structures: 【Chemistry 5】 【change】 In the formula, R ａ１ , R ａ２ , R ａ３ each independently represents hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, aryl group, heteroalkyl group, heterocycloalkyl group, heteroaryl group, haloalkyl group, haloaryl group, haloheteroaryl group, alkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxy group, mercapto group, nitro group, cyano group, amino group, mono- or di-alkylamino group, mono- or diarylamino group, ester group, nitrile group, isonitrile group, heteroaryl group, alkoxycarbonyl group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, sulfinyl group, carbamide group, phosphoramide group, imine group, sulfo group, carboxy group, hydrazino group, substituted silyl group, or a combination thereof; In the formula, R ｂ１ , R ｃ１ , R ｃ２ each independently represents mono-, di-, tri-, or tetra-substituted or unsubstituted, and R ｂ１ , R ｃ１ , R ｃ２ are each independently hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, aryl group, heteroalkyl group, heterocycloalkyl group, heteroaryl group, haloalkyl group, haloaryl group, haloheteroaryl group, alkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxy group, mercapto group, nitro group, cyano group, amino group, mono- or di-alkylamino group, mono- or diarylamino group, ester group, nitrile group, isonitrile group, heteroaryl group, alkoxycarbonyl group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, sulfinyl group, carbamide group, phosphoramide group, imine group, sulfo group, carboxy group, hydrazino group, substituted silyl group, or a combination thereof; ｂ１ , R ｃ１ and R ｃ２ wherein the carbon atoms may be selectively bonded to form a fused ring.

4. The central chiral segment L according to claim 3 ａ The specific structure of is preferably selected from the following structures, but is not limited thereto: 【Chemistry 6】 【change】 【change】 In the formula, R ｄ１ represents mono-, di-, tri- or tetra-substituted or unsubstituted, and R ｂ１ are independently hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, aryl group, heteroalkyl group, heterocycloalkyl group, heteroaryl group, haloalkyl group, haloaryl group, haloheteroaryl group, alkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxy group, mercapto group, nitro group, cyano group, amino group, mono- or di-alkylamino group, mono- or diarylamino group, ester group, nitrile group, isonitrile group, heteroaryl group, alkoxycarbonyl group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, sulfinyl group, carbamide group, phosphoramide group, imine group, sulfo group, carboxy group, hydrazino group, substituted silyl group, or a combination thereof; ｄ１ may optionally be bonded to form a fused ring, In the formula, R ｅ１ , R ｅ２ , R ｅ３ , R ｅ４ and independently represent hydrogen, deuterium, halogen, alkyl group, cycloalkyl group, aryl group, heteroalkyl group, heterocycloalkyl group, heteroaryl group, haloalkyl group, haloaryl group, haloheteroaryl group, alkoxy group, aryloxy group, alkenyl group, cycloalkenyl group, alkynyl group, hydroxy group, mercapto group, nitro group, cyano group, amino group, mono- or di-alkylamino group, mono- or diarylamino group, ester group, nitrile group, isonitrile group, heteroaryl group, alkoxycarbonyl group, acylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfonylamino group, sulfamoyl group, carbamoyl group, alkylthio group, sulfinyl group, carbamide group, phosphoramide group, imine group, sulfo group, carboxy group, hydrazino group, substituted silyl group, or a combination thereof.

5. The central chirality-induced spiro-chirality tetradentate cyclometalated platinum(II) and palladium(II) complex circularly polarized luminescent material according to claim 1 or 2, preferably selected from the following structures, but not limited thereto: 【Chemistry 7】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 【change】 In the formula, M is Pt or Pd, and R and R′ each independently represent hydrogen, deuterium, a halogen, an alkyl group, a cycloalkyl group, an aryl group, a heteroalkyl group, a heterocycloalkyl group, a heteroaryl group, a haloalkyl group, a haloaryl group, a haloheteroaryl group, an alkoxy group, an aryloxy group, an alkenyl group, a cycloalkenyl group, an alkynyl group, a hydroxy group, a mercapto group, a nitro group, a cyano group, an amino group, a mono- or di-alkylamino group, a mono- or diarylamino group, an ester ... and circularly polarized luminescent materials comprising spiro-chirality tetradentate cyclometalated platinum(II) and palladium(II) complexes each having a substituted aryl group, a nitrile group, an isonitrile group, a heteroaryl group, an alkoxycarbonyl group, an acylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a sulfonylamino group, a sulfamoyl group, a carbamoyl group, an alkylthio group, a sulfinyl group, a carbamide group, a phosphoramide group, an imine group, a sulfo group, a carboxy group, a hydrazino group, or a substituted silyl group.

6. Use of the spiro-chirality tetradentate cyclometalated platinum(II) and palladium(II) complex circularly polarized luminescent material according to any one of claims 1 to 5 in light-emitting components, 3D display components, three-dimensional imaging components, optical information encryption components, information storage components, and bioimaging components.

7. 7. The use according to claim 6, wherein the light-emitting component is a light-emitting diode or a light-emitting electrochemical cell.

8. A full-color display comprising the light-emitting component according to claim 7.

9. A light-emitting display component comprising the light-emitting component according to claim 7.

10. 8. The use of claim 7, wherein the light-emitting component comprises a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, the organic layer comprising the spiro-chirality tetradentate cyclometallated platinum(II) and palladium(II) complex circularly polarized luminescent material according to claim 1.

11. 10. A display device comprising an organic light-emitting component, the organic light-emitting component comprising a first electrode, a second electrode, and at least one organic layer disposed between the first electrode and the second electrode, the organic layer comprising the spiro-chirality tetradentate cyclometallated platinum(II) and palladium(II) complex circularly polarized light-emitting material according to claim 1.

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