Bis-nuclear platinum (ii) red emitters for oled applications

Abstract

Described are platinum (II) complexes ("Pt(II) complexes") that can emit in the red and / or deep red region of the electromagnetic spectrum, and methods of making and using the same. These Pt(II) complexes can have binuclearity with close Pt-Pt contact and close interplanar spacing to achieve high emission quantum yield, such as > 50%, short emission lifetime, such as < 3 ps, and high radiative decay rate, such as 10 5 s ‑1 The Pt(II) complexes disclosed herein can be included in organic light emitting devices, such as organic light emitting diodes ("OLEDs"), for commercial applications. OLEDs containing these red-emitting Pt(II) complexes can have comparable or higher current efficiency and / or external quantum efficiency and extended operational lifetime, such as > 9000 h LT95 at 1000 nits for red OLEDs, than commercially available red emitters.

Description

[0001] Cross-reference to related applications

[0002] This application claims the benefit and priority of U.S. Provisional Application 63 / 195,139, filed May 31, 2021, the entire contents of which are incorporated herein by reference. Invention Field

[0003] This invention generally falls within the field of platinum(II) complexes and their use as red light emitters. Background of the Invention

[0005] Transition metal complexes have attracted considerable interest in both commercial and academic settings as molecular probes, catalysts, and luminescent materials. As luminescent materials, they are increasingly being explored as potential alternatives to purely organic materials due to their potential to improve luminescence efficiency compared to purely organic materials.

[0006] There is increasing attention and effort being put into adopting light-emitting diodes (LEDs). 8 Planar metallic complexes (e.g., Pt(II) and Au(III) complexes) serve as OLED emitters. However, the development of highly efficient red / deep red emitting Pt(II) complexes remains a challenge. According to the bandgap law, the nonradiative decay rate increases as the bandgap between the excited and ground states decreases. Assuming their radiative decay rates are the same, the emission quantum yield of red-emitting phosphorescent complexes is lower than that of blue- and green-emitting phosphorescent complexes. Currently available red-emitting Pt(II) complexes suffer from low room-temperature emission quantum yield (i.e., <50%), long emission lifetime (i.e., >3 μs), and short operating lifetime in OLEDs.

[0007] Pt(II) complexes that can emit in the red and / or deep red light regions are still needed.

[0008] Therefore, the object of the present invention is to provide Pt(II) complexes that emit in the red and / or deep red light regions.

[0009] A further object of the present invention is to provide a device containing a Pt(II) complex that emits in the red and / or deep red light regions.

[0010] A further object of the present invention is to provide a method for using Pt(II) complexes that emit in the red and / or deep red light regions. Invention Overview

[0012] Platinum(II) complexes (“Pt(II) complexes”) capable of emitting in the red and / or deep red light regions are described, along with their fabrication and use. These Pt(II) complexes can exhibit binuclearity, with close Pt-Pt contacts and close interplanar spacing, to achieve high emission quantum yields and high radiative decay rates, such as 10-1. 5 s -1 The magnitude.

[0013] The Pt(II) complex can have the structure of formula I':

[0014]

[0015] Wherein: (a) the compound may have an overall neutral charge, negative charge, or positive charge; (b) CY1, CY2, CY3, and CY4 may independently be substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, or substituted or unsubstituted cycloalkynyl; (c) R1, R2, R3, and R4 may independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted. (d) n1, n2, n3 and n4 may independently be integers from 0 to 10; (e) L1 and L3 may independently be bonds (single, double or triple), absent, oxygen, sulfur, amino, amide, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, carbonyl, sulfonyl, sulfonic acid, phosphoryl or phosphonyl; (f) R5, R6, R7 and R8 may independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl. (g) L2 and L4 may independently be bonds (single, double or triple), substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, amino, amide or carbonyl; (h) may be absent, bonds (single, double or triple), substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heterocyclic, alkoxy, aryloxy, ether, polyether, sulfonyl or thioether; The substituents mentioned in (i) may be independently substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyhexaaryl, substituted or unsubstituted aralkyl, substituted or unsubstituted carbonyl, substituted or unsubstituted alkoxy, halogen, hydroxyl, phenoxy, aryloxy, alkylthio, phenylthio, arylthio, cyano, isocyano, nitro, carboxyl, amino, amide, oxo, silyl, sulfinyl, sulfonyl, sulfonic acid, phosphonium, phosphanyl, phosphoryl, phosphonyl or thiol, or combinations thereof.

[0016] In some forms, the platinum(II) complex may have the structure of formula I or I”:

[0017]

[0018] In some forms, the platinum(II) complex may have the structure of formula II or II':

[0019]

[0020] Wherein: (a) CY2 and CY3 can be independently substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, or substituted or unsubstituted cycloynyl; (b) R2 and R3 can be independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, or substituted or unsubstituted polyheteroaryl. (c) n2, n3, n5 and n6 may be independently integers from 0 to 10; (d) R5, R6, R7 and R8 may be independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, alkoxy or aryloxy; (e) R9-R 14 and R 21 -R 24 (f) G1' and G2' can be independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol; (g) G1' and G2' can be independently C or N; (g) ------ can be absent, bond (single, double, or triple bond), substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, alkoxy, aryloxy, ether, polyether, sulfonyl, or thioether; and (h) the substituents can be as defined above for Formula I.

[0021] In some forms, the platinum(II) complex may have the structure of formula III or III”':

[0022]

[0023]

[0024] Wherein: (a) R5, R6, R7 and R8 may independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, alkoxy or aryloxy; (b) R9-R 24 It can independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol; (c) each ------ can independently be absent, bond ( (single, double, or triple bonds), substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, alkoxy, aryloxy, ether, polyether, sulfonyl, or thioether; (d) X1', X2', Y1', Y2', Y3', and Y4' may independently be O, S, CR 15 or NR 18 R 15 and R 18 It may be independently absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro or thiol; and (e) the substituent may be as defined above for Formula I.

[0025] In some forms, the platinum(II) complex may have the structure of formula IV or IV':

[0026]

[0027] Wherein: (a) R5, R6, R7 and R8 may independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, alkoxy or aryloxy; (b) R9-R 24 and R 27 -R 34(c) Each can independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol; (d) Each can independently be absent, bond (single, double, or triple bond), substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, alkoxy, aryloxy, ether, polyether, sulfonyl, or thioether; 25 or NR 26 R 25 and R 26 It may be independently absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro or thiol; and (e) the substituent may be as defined above for Formula I.

[0028] In some forms, R 11 R 12 R 21 R 22 It can be hydrogen, or R 11 and R 12 Together they can form and / or R 21 and R 22 Together they can form a structure of form V:

[0029]

[0030] Where: (a) Z' can be O, S, or CR 39 or NR 40 R 39 and R 40 (a) J1' and J2' can independently be absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol; (b) J1' and J2' can independently be R 41 and R42 (c) n7 can be independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol, and optionally, J1' and J2' together form a substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, or substituted or unsubstituted cycloalkynyl; and (d) R 35 -R 38 It can be independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro or thiol.

[0031] In some forms, the bonds between R5 and R8, R6 and R7, R5 and R7, and / or R6 and R8 may be absent, single bonds, substituted or unsubstituted alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, substituted or unsubstituted aryl groups, substituted or unsubstituted polyaryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted polyheteroaryl groups, substituted or unsubstituted heterocyclic groups, alkoxy groups, aryloxy groups, ethers, polyethers, sulfonyl groups, or thioethers. In some forms, and / or It can have the following structures: Wherein: (a) A' and B' may independently be substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, or substituted or unsubstituted heterocyclic; and (b) each occurrence of L5 may independently be an ether, polyether, alkoxy, thioether, sulfonyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted aryl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, or substituted or unsubstituted alkynyl. In some forms, A' and B' may independently be substituted or unsubstituted aryl or substituted or unsubstituted polyaryl; and L5 may have the following structure: Where: (a) Q1' and Q2' can be O or S independently; and (b) n9 can be an integer from 1 to 10, such as 1 to 6, for example 1, 2 or 6.

[0032] The Pt(II) complexes disclosed herein may be included in organic light-emitting devices for commercial applications, such as organic light-emitting diodes (“OLEDs”). Brief description of the attached diagram

[0034] Figure 1A-1F It shows Pt(II) complex 1a ( Figure 1A ), 1b ( Figure 1B ), 3a ( Figure 1C ), 3b Figure 1D ), 1c ( Figure 1E ) and 2b'( Figure 1F A schematic diagram of the X-ray crystal structure of ).

[0035] Figure 2A-2H It is displayed in PMMA ( Figure 2A ) and MCP ( Figure 2B Pt(II) complexes 1a and 1b in the membrane, in PMMA ( Figure 2C ) and MCP ( Figure 2D Pt(II) complexes 1b-1d and 1b'-1d' in the membrane, in PMMA ( Figure 2E ) and MCP ( Figure 2F Pt(II) complexes 2a-4a and 3b in the membrane and in CH2Cl2 ( Figure 2G ) and PMMA ( Figure 2H The emission spectra of Pt(II) complexes 2b and 2b' at room temperature are plotted.

[0036] Figures 3A-3D This is the electrochemiluminescence ("EL") spectrum of a device (system I) displaying Pt(II) complex 1a with doping concentrations of 6 wt%, 8 wt%, 10 wt%, and 12 wt%. Figure 3A ), external quantum efficiency ( Figure 3B ), luminous brightness ( Figure 3C ) and current density ( Figure 3D The curve of the system I device structure: ITO / HAT-CN (5nm) / TAPC (20nm) / Tris-PCz (10nm) / Tris-PCz:B4PYPPM:Pt-1a (30nm) / B4PYPPM (50nm) / Liq (1nm) / Al (100nm).

[0037] Figures 4A-4D This is the EL spectrum of a device (System II) displaying Pt(II) complex 1a with doping concentrations of 4 wt%, 8 wt%, 12 wt%, and 16 wt%. Figure 4A ), external quantum efficiency ( Figure 4B ), luminous brightness ( Figure 4C ) and current density ( Figure 4DThe curve of System II device structure: ITO / HAT-CN (5nm) / TAPC (40nm) / TCTA (10nm) / TCTA:TPBi:Pt-1a / TPBi (10nm) / TmPyPb (40nm) / LiF (1.2nm) / Al (100nm).

[0038] Figures 5A-5D This is the EL spectrum of a device displaying Pt(II) complex 1b with doping concentrations of 4 wt%, 12 wt%, and 16 wt%. Figure 5A ), external quantum efficiency ( Figure 5B ), luminous brightness ( Figure 5C ) and current density ( Figure 5D The curve of the device structure is as follows: ITO / HAT-CN (5nm) / TAPC (40nm) / TCTA (10nm) / TCTA:TPBi:Pt-1b (20nm) / TPBi (40nm) / LiF (1.2nm) / Al (100nm).

[0039] Figures 6A-6B This is the EL spectrum of a device displaying a Pt(II) complex 1d' containing a doping concentration of 4 wt%. Figure 6A ) and external quantum efficiency ( Figure 6B The curve of the device structure is as follows: ITO / HAT-CN (5nm) / TAPC (40nm) / TCTA (10nm) / Pt-1d':TCTA:TPBi (20nm) / TPBi (10nm) / TmPyPb (40nm) / LiF (1.2nm) / Al (100nm).

[0040] Figures 7A-7D This is the EL spectrum of a device containing a 6 wt% doping concentration of Pt(II) complex 2a and electron transport layers (“ETL”) at 40 nm, 80 nm, 100 nm, and 120 nm. Figure 7A ), external quantum efficiency ( Figure 7B ), radiation flux ( Figure 7C ), current density ( Figure 7D Figure 7 shows the curves of external quantum efficiency (Fig. 7E) and luminance (Fig. 7F). Device structure: ITO / HAT-CN (6nm) / TAPC (40nm) / TcTa (10nm) / Pt-2a (6 wt%):TcTa:TPBi (1:1) (20nm) / TPBi (10nm) / Liq:LE-T321 (1:1) (ETL) / Liq (1nm) / Al (100nm).

[0041] Figures 8A-8DThis is the EL spectrum of devices displaying Pt(II) complex 2a with doping concentrations of 4 wt%, 8 wt%, 12 wt%, and 16 wt%. Figure 8A ), external quantum efficiency ( Figure 8B ), luminous brightness ( Figure 8C ) and current density ( Figure 8D The curve of the device structure is as follows: ITO / HAT-CN (10nm) / Pt-2a (40nm) / compound-EB (5nm) / Pt-2a:compound-RH (40nm) / compound-HB (5nm) / compound-ET:Liq (35:65) (35nm) / Liq (1nm) / Al (100nm).

[0042] Figures 9A-9D This is the EL spectrum of a device displaying an ETL containing 6 wt% Pt(II) complex 4a at 40 nm, 80 nm, 100 nm, and 120 nm. Figure 9A ), external quantum efficiency ( Figure 9B ), radiation flux ( Figure 9C ) and current density ( Figure 9D The curve of the device structure is as follows: ITO / HAT-CN (6nm) / TAPC (40nm) / TcTa (10nm) / Pt-4a (6 wt%):TcTa:TPBi (1:1) (20nm) / TPBi (10nm) / Liq:LE-T321 (1:1) (ETL) / Liq (1nm) / Al (100nm).

[0043] Figure 10 This is a graph showing the device lifetime measurement results of vapor-deposited devices containing Pt(II) complex 1a with doping concentrations of 8 wt%, 12 wt%, and 16 wt%.

[0044] Figure 11 This is a graph showing the device lifetime measurement results of a vapor-deposited device containing a 4 wt% Pt(II) complex 1d'. Device structure: ITO / HAT-CN (10nm) / PT-301 (40nm) / compound-EB (5nm) / Pt-1d' (4 wt%): compound-RH (40nm) / compound-HB (5nm) / compound-ET: Liq (35:65) (35nm) / Liq (1nm) / Al (100nm).

[0045] Figure 12 This is a graph showing the device lifetime measurement results of vapor-deposited devices containing Pt(II) complex 2a with doping concentrations of 4 wt%, 8 wt%, 12 wt%, and 16 wt%.

[0046] Figure 13 This is a simplified diagram illustrating a non-limiting example of an organic light-emitting diode device 100 having a multilayer structure.

[0047] Figures 14A-14B This shows the EL spectra of vapor-deposited devices containing Pt(II) complex 1c with doping concentrations of 4 wt%, 8 wt%, and 16 wt%, respectively. Figure 14A ) and external quantum efficiency ( Figure 14B The curve of the device structure is as follows: ITO / HAT-CN (5nm) / TAPC (40nm) / TCTA (10nm) / Pt-1c:TCTA:TPBi (20nm) / TPBi (10nm) / TmPyPb (40nm) / LiF (1.2nm) / Al (100nm).

[0048] Figures 15A-15D This shows the EL spectra of vapor-deposited devices containing Pt(II) complex 2b' with doping concentrations of 4 wt%, 8 wt%, and 16 wt%, respectively. Figure 15A ), external quantum efficiency ( Figure 15B ), current density ( Figure 15C ) and luminous intensity ( Figure 15D The curve of the device structure is as follows: ITO / HAT-CN (5nm) / TAPC (40nm) / TCTA (10nm) / Pt-2b':TCTA:TPBi (20nm) / TPBi (10nm) / TmPyPb (40nm) / LiF (1.2nm) / Al (100nm).

[0049] Figure 16 This is a graph showing the lifetime measurement results of an OLED containing Pt(II) complex 1b.

[0050] Figure 17 This is a graph showing the lifetime measurement results of an OLED containing Pt(II) complex 1c.

[0051] Figure 18 This is a graph showing the lifetime measurement results of an OLED containing the Pt(II) complex 2b'. Invention Details

[0053] I. Definition

[0054] It should be understood that, unless otherwise stated, the disclosed complexes, compositions, and methods are not limited to specific synthetic methods, specific analytical techniques, or specific reagents, and therefore may vary. It should also be understood that the terminology used herein is for the purpose of describing particular forms and embodiments only and is not intended to constitute limitation.

[0055] As used herein, “substituted” means all permissible substituents of the compounds or functional groups described herein. In the broadest sense, permissible substituents include acyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, aromatic and non-aromatic substituents of organic compounds. Exemplary substituents include, but are not limited to, halogens, hydroxyl groups, or any other organic group containing any number of carbon atoms, preferably 1-14 carbon atoms, and optionally containing one or more heteroatoms, such as oxygen, sulfur, or nitrogen groups, in a straight-chain, branched, or cyclic form. Representative substituents include substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted phenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyhexaaryl, substituted or unsubstituted aralkyl, halogen, hydroxyl, alkoxy, phenoxy, aryloxy, silyl, thiol, alkylthio, substituted alkylthio, phenylthio, arylthio, cyano, isocyano, nitro, substituted or unsubstituted carbonyl, carboxyl, amino, amide, oxo, sulfinyl, sulfonyl, sulfonic acid, phosphonium, phosphonyl, phosphoryl, phosphonyl, and amino acids. Such substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted phenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyhexaaryl, substituted or unsubstituted aralkyl, halogen, hydroxyl, alkoxy, phenoxy, aryloxy, silyl, thiol, alkylthio, substituted alkylthio, phenylthio, arylthio, cyano, isocyano, nitro, substituted or unsubstituted carbonyl, carboxyl, amino, amide, oxo, sulfinyl, sulfonyl, sulfonic acid, phosphonium, phosphonyl, phosphoryl, phosphonyl and amino acids can be further substituted.

[0056] Heteroatoms such as nitrogen may have hydrogen substituents and / or any permitted substituents in the organic compounds described herein that satisfy the valence of the heteroatoms. It is to be understood that “substitution” or “substituted” includes the implicit condition that such substitution satisfies the permitted valence of the substituted atom and the substituent, and that the substitution produces a stable compound, i.e., a compound that does not spontaneously undergo transformation (e.g., by rearrangement, cyclization, elimination, etc.).

[0057] As used herein, "alkyl" refers to a radical group of saturated aliphatic groups, including straight-chain alkyl, branched-chain alkyl, and cycloalkyl (alicyclic). In some forms, straight-chain or branched alkyl groups have 30 or fewer carbon atoms in their main chain (e.g., for straight-chain C1-C1 alkyl groups). 30 For the C3-C branch 30Alkyl groups have 20 or fewer carbon atoms, 15 or fewer carbon atoms, or 10 or fewer carbon atoms. Alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, decyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, etc. Similarly, cycloalkyl groups are non-aromatic carbonyl rings consisting of at least three carbon atoms, such as those containing 3-30, 3-20, or 3-10 carbon atoms in their ring structure, and non-aromatic monocyclic or non-aromatic polycyclic rings having 5, 6, or 7 carbon atoms in their ring structure. Cycloalkyl groups containing polycyclic ring systems may have two or more non-aromatic rings, where two or more carbons are shared by two adjacent rings (i.e., "fused cycloalkyl rings"). Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc.

[0058] As used throughout this specification, examples, and claims, the term "alkyl" is intended to include both "unsubstituted alkyl" and "substituted alkyl," the latter referring to an alkyl group having one or more substituents replacing hydrogen on one or more carbons of the hydrocarbon backbone. Such substituents can be any of the substituents listed above, such as halogens (e.g., fluorine, chlorine, bromine, or iodine), hydroxyl groups, carbonyl groups (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), thiocarbonyl groups (e.g., thioesters, thioacetates, or thiocarbamates), aryl, alkoxy, aralkyl, phosphonyl, phosphonyl, phosphoryl, phosphate, phosphonate, phosphinate, amino, amide, amidine, imine, cyano, nitro, azide, oxo, mercapto, thiol, alkylthio, silyl, sulfinyl, sulfate, sulfonate, aminosulfonyl, sulfonamide, sulfonyl, heterocyclic, aromatic. Or heteroaryl groups; -NRR', wherein R and R' are independently hydrogen, alkyl, or aryl, and wherein the nitrogen atom is optionally quaternized; -SR, wherein R is phosphono, sulfinyl, silyl, hydrogen, alkyl, or aryl; -CN; -NO2; -COOH; carboxylic esters; -COR, -COOR, or -CON(R)2, wherein R is hydrogen, alkyl, or aryl; imino, silyl, ether, haloalkyl (e.g., -CF3, -CH2-CF3, -CCl3); -CN; -NCOCOCH2CH2; -NCOCOCHCH; and -NCS; and combinations thereof. The term "alkyl" also includes "heteroalkyl".

[0059] Those skilled in the art will understand that, where appropriate, the substituent group on the hydrocarbon chain can itself be substituted. For example, substituents for substituted alkyl groups may include halogens, hydroxyl groups, nitro groups, thiols, amino groups, aralkyl groups, azide groups, imino groups, amide groups, phosphonium groups, phosphonyl groups (including phosphonates and hypophosphonates), oxo groups, sulfonyl groups (including sulfates, sulfonamides, aminosulfonyl groups, and sulfonates), and silyl groups, as well as ethers, alkylthio groups, carbonyl groups (including ketones, aldehydes, carboxylic acid esters, and esters), haloalkyl groups, -CN groups, etc. Cycloalkyl groups can be substituted in the same manner.

[0060] Unless otherwise specified, “low carbon alkyl” as used herein refers to an alkyl group as defined above but having 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, in its main chain structure. Similarly, “low carbon alkenyl” and “low carbon alkynyl” have similar chain lengths.

[0061] As used herein, “heteroalkyl” means a straight-chain, branched, or cyclic carbon-containing alkyl group or combination thereof containing at least one heteroatom. Suitable heteroatoms include, but are not limited to, O, N, Si, P, and S, wherein nitrogen, phosphorus, and sulfur atoms are optionally oxidized, and the nitrogen heteroatom is optionally quaternized. For example, the term “heterocycloalkyl” is a cycloalkyl group as defined above in which at least one carbon atom of the ring is substituted with a heteroatom, such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus.

[0062] As used herein, the term "alkenyl" refers to a hydrocarbon group having a structural formula of 2 to 24 carbon atoms and containing at least one carbon-carbon double bond. Alkenes include straight-chain alkenes, branched alkenes, and cycloalkenes. Cycloalkenes are non-aromatic carbonyl rings consisting of at least three carbon atoms and at least one carbon-carbon double bond, such as those containing 3-30 carbon atoms and at least one carbon-carbon double bond, 3-20 carbon atoms and at least one carbon-carbon double bond, or 3-10 carbon atoms and at least one carbon-carbon double bond in their ring structure, and non-aromatic monocyclic or non-aromatic polycyclic rings having 5, 6, or 7 carbon atoms and at least one carbon-carbon double bond in their ring structure. Cycloalkenes containing polycyclic ring systems may have two or more non-aromatic rings, wherein two or more carbons are shared by two adjacent rings (i.e., "fused cycloalkenyl rings") and contain at least one carbon-carbon double bond. Asymmetric structures such as (AB)C=C (C'D) are intended to include E and Z isomers. This can be inferred from the structural formulas herein, where an asymmetric olefin is present, or which may be explicitly indicated by the bond symbol C. As used throughout the specification, examples, and claims, the term "alkenyl" is intended to include both "unsubstituted alkenyl" and "substituted alkenyl," the latter referring to an alkenyl group having one or more substituents replacing hydrogen on one or more carbons of the hydrocarbon backbone. The term "alkenyl" also includes "heteroalkenyl."

[0063] The term "substituted alkenyl" refers to an alkenyl group having one or more substituents replacing one or more hydrogen atoms on one or more carbons of the hydrocarbon backbone. Such substituents can be any of the substituents listed above, such as halogens, azides, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thiocarbamate), alkoxy, phosphonium, phosphonyl, phosphoryl, phosphate, phosphonate, hypophosphonate, amino (e.g., quaternized amino), amide, amidine, imine, cyano, nitro, azide, oxo, mercapto, alkylthio, sulfate, sulfonate, aminosulfonyl, sulfonylamino, sulfonyl, heterocyclic, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof.

[0064] As used herein, “heteroalkenyl” refers to a straight-chain, branched, or cyclic carbon-containing alkenyl group or combination thereof containing at least one heteroatom. Suitable heteroatoms include, but are not limited to, O, N, Si, P, and S, wherein nitrogen, phosphorus, and sulfur atoms are optionally oxidized, and the nitrogen heteroatom is optionally quaternized. For example, the term “heterocyclic alkenyl” is a cycloalkenyl group in which at least one carbon atom of the ring is substituted by a heteroatom, such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus.

[0065] As used herein, the term "alkynyl" refers to a hydrocarbon group having a structure of 2 to 24 carbon atoms and containing at least one carbon-carbon triple bond. Alynyl groups include straight-chain alkynyls, branched-chain alkynyls, and cycloalkynyls. A cycloalkynyl is a non-aromatic carbonyl ring consisting of at least three carbon atoms and at least one carbon-carbon triple bond, such as having 3-30 carbon atoms and at least one carbon-carbon triple bond, 3-20 carbon atoms and at least one carbon-carbon triple bond, or 3-10 carbon atoms and at least one carbon-carbon triple bond in its ring structure, and a non-aromatic monocyclic or non-aromatic polycyclic ring having 5, 6, or 7 carbon atoms and at least one carbon-carbon triple bond in its ring structure. Cycloalkynyls containing polycyclic ring systems may have two or more non-aromatic rings, wherein two or more carbons are shared by two adjacent rings (i.e., "fused cycloalkynyl rings") and contain at least one carbon-carbon triple bond. Asymmetric structures such as (AB)C≡C(C”D) are intended to include E and Z isomers. This can be inferred from the structural formula herein in which an asymmetric alkyne is present, or it can be explicitly indicated by the bond symbol C. As used throughout the specification, examples, and claims, the term "alkynyl" is intended to include both "unsubstituted alkynyl" and "substituted alkynyl," the latter referring to an alkynyl group having one or more substituents replacing hydrogen on one or more carbons of the hydrocarbon backbone. The term "alkynyl" also includes "heterynyl."

[0066] The term "substituted alkynyl" refers to an alkynyl group having one or more substituents replacing one or more hydrogen atoms on one or more carbons of the hydrocarbon backbone. Such substituents can be any of the substituents listed above, such as halogens, azides, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thiocarbamate), alkoxy, phosphonium, phosphonyl, phosphoryl, phosphate, phosphonate, hypophosphonate, amino (e.g., quaternized amino), amide, amidine, imine, cyano, nitro, azide, mercapto, alkylthio, sulfate, sulfonate, aminosulfonyl, sulfonylamino, sulfonyl, heterocyclic, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof.

[0067] As used herein, “heteroyne” refers to a straight-chain, branched, or cyclic carbonaceous ynyl group or combination thereof containing at least one heteroatom. Suitable heteroatoms include, but are not limited to, O, N, Si, P, and S, wherein nitrogen, phosphorus, and sulfur atoms are optionally oxidized, and the nitrogen heteroatom is optionally quaternized. For example, the term “heterocyclic ynyl” is a cyclic ynyl group in which at least one carbon atom of the ring is substituted by a heteroatom, such as, but not limited to, nitrogen, oxygen, sulfur, or phosphorus.

[0068] As used in this article, the term "aryl" refers to any C5-C 26 Carbonyl aromatic groups, heteroaromatic groups, fused aromatic groups, or fused heteroaromatic groups. For example, as used herein, "aryl" may include 5-, 6-, 7-, 8-, 9-, 10-, 14-, 18-, and 24-membered monocyclic aromatic groups, including but not limited to benzene, naphthalene, anthracene, phenanthrene, etc. Examples of aryl groups include pyrene, corannulene, and benzene. "Aryl" further includes polycyclic systems having two or more cyclic rings, where two or more carbons are shared by two adjacent rings (i.e., "fused aromatic rings"), and where at least one ring is aromatic; for example, the other one or more cyclic rings can be cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, and / or heterocyclic. Aryl groups can be substituted with one or more groups, including but not limited to alkyl, alkynyl, alkenyl, aryl, halides, nitro, amino, esters, ketones, aldehydes, hydroxyl, carboxylic acids, or alkoxy groups.

[0069] The term "substituted aryl" refers to an aryl group in which one or more hydrogen atoms on one or more aromatic rings are replaced by one or more substituents. Such substituents can be any of the substituents listed above, such as halogens, azides, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, alkoxy, carbonyl (e.g., ketones, aldehydes, carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ethers, esters, thiocarbonyl (e.g., thioesters, thioacetates, or thiocarbamates), alkoxy, phosphonium, phosphoryl, phosphoryl, phosphate, phosphonate, hypophosphonate, amino (e.g., quaternized amino), amide, amidine, imine, cyano, nitro, azide, mercapto, imino, alkylthio, sulfate, sulfonate, aminosulfonyl, sulfonylamino, sulfonyl, heterocyclic, alkylaryl, haloalkyl (e.g., CF3, -CH2-CF3, -CCl3), -CN, aryl, heteroaryl, and combinations thereof.

[0070] "Heterocycle" and "heterocyclic group" are used interchangeably, and refer to a cyclic group consisting of a non-aromatic monocyclic or polycyclic ring with 3-30, 3-20, 3-10, or 5-6 ring atoms linked by cyclic carbon or nitrogen atoms, optionally containing 1-3 double bonds and optionally substituted by one or more substituents, wherein each ring contains carbon and 1 to 4 heteroatoms selected from non-peroxide oxygen, sulfur, and N (Y), wherein Y is absent or H, O, C1-C 1o Alkyl, phenyl, or benzyl. By definition, heterocyclic groups are distinct from heteroaryl groups. Heterocyclic groups can be heterocyclic alkyl, heterocyclic alkenyl, heterocyclic alkynyl, etc., such as piperazinyl, piperidinyl, piperidinoneyl, 4-piperidinoneyl, dihydrofurano[2,3-b]tetrahydrofuran, morpholinyl, piperazinyl, piperidinyl, piperidinoneyl, 4-piperidinoneyl, piperinyl, pyranyl, 2H-pyrroleyl, 4H-quinazinyl, quininecycloyl, tetrahydrofuranyl, 6H-1,2,5-thiadiazinyl. Heterocyclic groups may optionally be substituted by one or more substituents as defined above with respect to alkyl and aryl groups.

[0071] The term "heteroaryl" refers to C5-C 30A heteroaryl group is a monocyclic aromatic ring system, a fused aromatic ring system, a diaromatic ring system, or a combination thereof, wherein one or more carbon atoms in one or more aromatic ring structures have been replaced by heteroatoms. Suitable heteroatoms include, but are not limited to, oxygen, sulfur, and nitrogen. In a broader sense, as used herein, “heteroaryl” includes 5-, 6-, 7-, 8-, 9-, 10-, 14-, 18-, and 24-membered monocyclic aromatic groups that may contain 1 to 4 heteroatoms, such as pyrrole, furan, thiophene, imidazole, oxazole, thiazole, triazole, tetraazole, pyrazole, pyridine, pyrazine, pyridazine, and pyrimidine. Heteroaryl groups may also be referred to as “aryl heterocycles” or “heteroaromatic compounds.” “Heteroaryl” further includes polycyclic ring systems having two or more rings, wherein two or more carbons are common to two adjacent rings (i.e., “fused rings”), wherein at least one ring is heteroaromatic; for example, the other one or more cyclic rings may be cycloalkyl, cycloalkenyl, cycloalkynyl, aryl, heterocyclic, or combinations thereof. Examples of heteroaryl rings include, but are not limited to, benzimidazolyl, benzofuranyl, benzothiofuranyl, benzothiophene, benzooxazolyl, benzooxazolinyl, benzothiazolyl, benzotriazolyl, benzotetrazole, benzoisooxazolyl, benzoisothiazolyl, benzimidazolinyl, carbazole, 4aH-carbazole, carbolinyl, benzodihydropyranyl, benzopyranyl, cenylyl, decahydroquinolinyl, 2H,6H-1,5,2-dithiazinyl, furanyl, furazanyl (… furazanyl), imidazolinyl, imidazolinyl, 1H-indazole, indolenyl, dihydroindole, indazinyl, indole, 3H-indole, isatinoyl, isobenzofuranyl, isochromanyl, isoindazole, isoindolelinyl, isoindole, isoquinolinyl, isothiazolyl, isoxazolyl, methylenedioxyphenyl, naphthidyl, octahydroisoquinolinyl, 1,2, 3-Oxadiazolyl, 1,2,4-Oxadiazolyl, 1,2,5-Oxadiazolyl, 1,3,4-Oxadiazolyl, Oxazolylalkyl, Oxazolyl, Oxindolyl, Pyrimidinyl, Phenyridinyl, Phenyrheolinyl, Phenoxathinyl, Phenoxazinyl, Phtharazineyl, Pteridinyl, Purine, Pyrazinyl, Pyrazolylalkyl, Pyrazolinyl, Pyrazolyl, Pyridazinyl, Pyridooxazole, Pyridoimidazole ), pyridothiazole, pyridinyl, pyridyl, pyrimidinyl, pyrrolidinyl, pyrrolinyl, pyrroleyl, quinazolinyl, quinolinyl, quinoxalinyl, tetrahydroisoquinolinyl, tetrahydroquinolinyl, tetrazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,2,5-thiadiazolyl, 1,3,4-thiadiazolyl, thianyl, thiazolyl, thienyl, thienothiazolyl, thienooxazolyl, thienoimidazolyl, thienyl and xanthonyl.One or more rings may be substituted as defined below for "substituted heteroaryl".

[0072] The term "substituted heteroaryl" refers to a heteroaryl group in which one or more hydrogen atoms on one or more heteroaryl rings are replaced by one or more substituents. Such substituents can be any of the substituents listed above, such as halogens, azides, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, alkoxy, carbonyl (e.g., ketones, aldehydes, carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ethers, esters, thiocarbonyl (e.g., thioesters, thioacetates, or thiocarbamates), alkoxy, phosphonium, phosphoryl, phosphoryl, phosphate, phosphonate, hypophosphonate, amino (e.g., quaternized amino), amide, amidine, imine, cyano, nitro, azide, mercapto, imino, alkylthio, sulfate, sulfonate, aminosulfonyl, sulfonylamino, sulfonyl, heterocyclic, alkylaryl, haloalkyl (e.g., CF3, -CH2-CF3, -CCl3), -CN, aryl, heteroaryl, and combinations thereof.

[0073] The term "polyaryl" refers to a chemical group comprising two or more aryl, heteroaryl, and combinations thereof. Aryl, heteroaryl, and combinations thereof are fused or linked via single bonds, ethers, esters, carbonyl groups, amides, sulfonyl groups, sulfonamides, alkyl groups, azo groups, and combinations thereof. For example, a "polyaryl" can be a polycyclic aromatic hydrocarbon system having two or more cyclic rings, wherein two or more carbons are shared by two adjacent rings (i.e., "fused aromatic rings"), wherein two or more rings are aromatic. When two or more heteroaryl groups are involved, the chemical group can be referred to as a "polyheteroaryl".

[0074] The term "substituted polyaryl" refers to a polyaryl group in which one or more aryl or heteroaryl groups are replaced by one or more substituents. Such substituents can be any of the substituents listed above, such as halogens, azides, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thiocarbamate), alkoxy, phosphonium, phosphonyl, phosphoryl, phosphate, phosphonate, hypophosphonate, amino (e.g., quaternized amino), amide, amidine, imine, cyano, nitro, azide, mercapto, alkylthio, sulfate, sulfonate, aminosulfonyl, sulfonylamino, sulfonyl, heterocyclic, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof. When two or more heteroaryl groups are involved, the chemical group may be referred to as a "substituted polyaryl".

[0075] The term "cyclic ring" refers to a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted polycyclic ring (such as those formed from monocyclic or fused ring systems), such as substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloynyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, and substituted or unsubstituted polyheteroaryl, having 3 to 30 carbon atoms, provided that geometric constraints allow. The substituted cycloalkyl, cycloalkenyl, cycloynyl, and heterocyclic groups are substituted as defined above for alkyl, alkenyl, ynyl, heterocyclic, aryl, heteroaryl, polyaryl, and polyheteroaryl, respectively.

[0076] As used herein, the term "aralkyl" refers to an aryl or heteroaryl group having an alkyl, ynyl, or alkenyl group as defined above attached to an aromatic group, such as an aryl, heteroaryl, polyaryl, or polyheteroaryl group. An example of an aralkyl group is a benzyl group.

[0077] The terms "alkoxy" ("alkoxyl" or "alkoxy") and "aroxy" ("aroxy" or "aryloxy") are generally used to describe compounds derived from the formula -OR v The compound represented by R v This includes, but is not limited to, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted heterocyclic alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyhexaaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroalkyl, substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted carbonyl, phosphonium, phosphonyl, phosphonyl, sulfinyl, silyl, thiol, amide, and amino. Exemplary alkoxy groups include methoxy, ethoxy, propoxy, tert-butoxy, etc. "Low-carbon alkoxy" refers to an alkoxy group containing 1 to 6 carbon atoms. "Ether" is two functional groups covalently linked by oxygen as defined below. Therefore, the substituent of the alkyl group that makes the alkyl group an ether is or similar to an alkoxy group, and may be represented by one of the following: -O-alkyl, -O-alkenyl, -O-ynyl, -O-aryl, -O-heteroaryl, -O-polyaryl, -O-polyheteroaryl, -O-heterocyclic, etc.

[0078] The term "substituted alkoxy" refers to an alkoxy group having one or more substituents replacing one or more hydrogen atoms on one or more carbons of the alkoxy backbone. Such substituents can be any of the substituents listed above, such as halogens, azides, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thiocarbamate), alkoxy, phosphonium, phosphoryl, phosphoryl, phosphate, phosphonate, hypophosphonate, amino (e.g., quaternized amino), amide, amidine, imine, cyano, nitro, azide, mercapto, alkylthio, oxo, sulfate, sulfonate, aminosulfonyl, sulfonylamino, sulfonyl, heterocyclic, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0079] As used in this article, the term "ether" is derived from formula A. 2 OA 1 It means that A 2 and A 1 It can be independently substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted aralkyl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyhexaaryl, phosphonium, phosphonyl, phosphonyl, sulfinyl, silyl, thiol, substituted or unsubstituted carbonyl, alkoxy, amide or amino.

[0080] The term "polyether" as used in this article is represented by the following formula:

[0081]

[0082] Where A 3 A 2 and A 1 It can be independently a substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted aralkyl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyhexaaryl, phosphonyl, substituted or unsubstituted carbonyl, alkoxy, amide or amino; g can be a positive integer from 1 to 30.

[0083] The term "phenoxy" is recognized in the art and refers to the formula -OR v The compound in which R v Yes (i.e., -O-C6H5). Those skilled in the art will recognize that phenoxy groups belong to the aryloxy group.

[0084] The term "substituted phenoxy" refers to a phenoxy group as defined above, having one or more substituents replacing one or more hydrogen atoms on one or more carbons of a benzene ring. Such substituents include, but are not limited to, halogens, azides, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (such as carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (such as thioester, thioacetate, or thiocarbamate), alkoxy, phosphonium, phosphonyl, phosphonyl, phosphoryl, phosphate, phosphonate, hypophosphonate, amino (e.g., quaternized amino), amide, amidine, imine, cyano, nitro, azide, mercapto, alkylthio, sulfate, sulfonate, aminosulfonyl, sulfonylamino, sulfonyl, heterocyclic, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0085] The terms “aroxy” and “aryloxy”, which are used interchangeably herein, are denoted by -O-aryl or -O-heteroaryl, where aryl and heteroaryl are as defined herein.

[0086] The terms “substituted aryloxy” and “substituted aryloxy”, which are used interchangeably herein, refer to an -O-aryl or -O-heteroaryl group having one or more substituents replacing one or more hydrogen atoms on one or more ring atoms of an aryl or heteroaryl group as defined herein. Such substituents can be any of the substituents mentioned above, such as halogens, azides, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thiocarbamate), alkoxy, phosphonium, phosphonyl, phosphonyl, phosphoryl, phosphate, phosphonate, hypophosphonate, amino (e.g., quaternized amino), amide, amidine, imine, cyano, nitro, azide, mercapto, alkylthio, sulfate, sulfonate, aminosulfonyl, sulfonylamino, sulfonyl, heterocyclic, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof.

[0087] As used herein, the term "amino" includes groups.

[0088]

[0089] Where E is absent, or E is a substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, wherein independent of E, R x R xi and R xiiEach of these groups independently represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aralkyl group (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl), a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, a substituted or unsubstituted heterocyclic group, a hydroxyl group, an alkoxy group, a phosphonyl group, a phosphonyl group, a sulfinyl group, a silyl group, a thiol group, an amide group, an amino group, or -(CH2). m -R”'; R”' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, an alkoxy group, a phosphonyl group, an amide group, or an amino group; and m is 0 or an integer from 1 to 8. The term "quaternary amino" also includes nitrogen, R x R xi and R xii N connected to them + Together they form a heterocyclic or heteroaryl group having 3 to 14 atoms in a ring structure.

[0090] The terms "amide" or "acylamino" are used interchangeably to refer to "unsubstituted acylamino" and "substituted acylamino," and are represented by the following general formula:

[0091]

[0092] Where E is absent, or E is a substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, or substituted or unsubstituted heterocyclic group, wherein independently of E, R and R' each independently represent hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic group, hydroxyl, alkoxy, phosphonylphosphonylsulfinyl, silylthiol, amide-amino, or -(CH2). m-R”', or R and R' together with their associated N atoms, constitute a heterocycle having 3 to 14 atoms in the ring structure; R”' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, an alkoxy group, a phosphonyl group, an amide group, or an amino group; and m is 0 or an integer from 1 to 8. In some forms, when E is oxygen, a carbamate is formed.

[0093] As used herein, “carbonyl” is a term recognized in the art and includes groups that can be represented by the following general formula:

[0094]

[0095] Where X is a bond, or represents oxygen or sulfur, and R represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, hydroxyl, alkoxy, phosphonium, phosphonyl, amide, amino, or -(CH2). m -R”, or a pharmaceutically acceptable salt; E” is absent, or E” is a substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic group; R' represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclic group, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic group, hydroxyl, alkoxy, phosphonium, phosphoalkyl, amide, amino, or -(CH2). m-R”; R” represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyhexaaryl group, an alkoxy group, a phosphonyl group, an amide group, or an amino group; and m is 0 or an integer from 1 to 8. When X is oxygen and R is as defined above, the group is also called a carboxyl group. When X is oxygen and R is hydrogen, the formula represents a “carboxylic acid”. When X is oxygen and R’ is hydrogen, the formula represents a “formate ester”. When X is oxygen and R or R’ is not hydrogen, the formula represents an “ester”. Generally, when the oxygen atom in the above formula is replaced by a sulfur atom, the formula represents a “thiocarbonyl”. When X is sulfur and R or R’ is not hydrogen, the formula represents a “thioester”. When X is sulfur and R is hydrogen, the formula represents a “thiocarboxylic acid”. When X is sulfur and R' is hydrogen, the formula represents "thiocarbamate". When X is a bond and R is not hydrogen, the formula represents "ketone". When X is a bond and R is hydrogen, the formula represents "aldehyde".

[0096] The term "substituted carbonyl" refers to a carbonyl group as defined above, wherein R, R', or a group One or more hydrogen atoms in the attached group are independently substituted. Such substituents can be any of the substituents listed above, such as halogens, azides, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thiocarbamate), alkoxy, phosphonium, phosphoryl, phosphoryl, phosphate, phosphonate, hypophosphonate, amino (e.g., quaternized amino), amide, amidine, imine, cyano, nitro, azide, mercapto, alkylthio, sulfate, sulfonate, aminosulfonyl, sulfonylamino, sulfonyl, heterocyclic, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0097] The term "carboxyl group" is as defined above for the carbonyl group, and more specifically by the formula -R iv COOH is defined, where R iv It is a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclic, a substituted or unsubstituted alkylaryl, a substituted or unsubstituted arylalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyheteroaryl, or a substituted or unsubstituted heteroaryl.

[0098] The term "substituted carboxyl group" refers to the group in which R... ivOne or more hydrogen atoms in the carboxyl groups as defined above are substituted. Such substituents may be any of the above substituents, such as halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (such as carboxyl, alkoxycarbonyl, formyl or acyl), silyl, ether, ester, thiocarbonyl (such as thioester, thioacetate or thioformate), alkoxy, phosphonium, phosphino, phosphoryl, phosphate, phosphonate, phosphinate, amino (such as quaternized amino), amido, amidine, imine, cyano, nitro, azido, mercapto, alkylthio, sulfate, sulfonate, sulfamoyl, sulfonamido, sulfonyl, heterocyclic group, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl and combinations thereof.

[0099] The term "phosphino" is represented by the following formula

[0100]

[0101] where E is absent, or E is a substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic group, where independently of E, R vi and R vii each independently represent hydrogen, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted carbonyl, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aralkyl (such as substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted heterocyclic group, hydroxyl, alkoxy, phosphonium, phosphino, phosphoryl, sulfinyl, silyl, thiol, amido, amino or -(CH2) m -R''', or R vi and R vii together with the P atom to which they are attached form a heterocyclic ring having 3 to 14 atoms in the ring structure; R''' represents hydroxyl, a substituted or unsubstituted carbonyl, a substituted or unsubstituted aryl, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted cycloalkenyl, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyheteroaryl, alkoxy, phosphonium, phosphino, amido or amino; and m is 0 or an integer from 1 to 8.

[0102] The term "phosphonium" is represented by the following formula

[0103]

[0104] Where E is absent, or E is a substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, wherein independent of E, R vi R vii and R viii Each of these groups independently represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, hydroxyl, alkoxy, phosphonium, phosphonyl, sulfinyl, silyl, thiol, amide, amino, or -(CH2). m -R”', or R vi R vii and R viii P connected to them + The atoms together form a heterocycle having 3 to 14 atoms in a ring structure; R”' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, an alkoxy group, a phosphonyl group, an amide group, or an amino group; and m is an integer from 0 to 8.

[0105] The term "phosphonoyl" is represented by the following formula.

[0106]

[0107] Where E is absent, or E is a substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, oxygen, alkoxy, aryloxy, or substituted alkoxy or substituted aryloxy, wherein independent of E, R vi and R viiIndependently, it can be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, hydroxyl, alkoxy, phosphonium, phosphonyl, sulfinyl, silyl, thiol, amide, amino, or -(CH2). m -R”', or R vi and R vii Together with the P atoms to which they are attached, they form a heterocycle having 3 to 14 atoms in the ring structure; R”' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, an alkoxy group, a phosphonyl group, an amide group, or an amino group; and m is an integer from 0 to 8.

[0108] The term "substituted phosphonoyl group" represents that E, R vi and R vii Independently substituted phosphonoyl group. Such substituents can be any of the above-mentioned substituents, such as halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thiocarbamate), alkoxy, phosphoryl, phosphate, phosphonate, hypophosphonate, amino (e.g., quaternized amino), amide, amidine, imine, cyano, nitro, azide, mercapto, alkylthio, sulfate, sulfonate, aminosulfonyl, sulfonylamino, sulfonyl, heterocyclic, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof.

[0109] The term "phosphonyl" is defined as follows: where E is absent, oxygen, alkoxy, aryloxy, substituted alkoxy, or substituted aryloxy as defined above, and R is independent of E. vi and R vii Independently, it can be a hydroxyl, alkoxy, aryloxy, substituted alkoxy, or substituted aryloxy group as defined above. As will be understood by those skilled in the art, when E is oxygen, the phosphoryl group cannot be attached to another class of chemicals, for example, to form an oxygen-oxygen bond or other unstable bond. When E, R... vi and Rv iiWhen substituted, the substituents include, but are not limited to, halogens, azides, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (such as carboxyl, alkoxycarbonyl, formyl or acyl), silyl, ether, ester, thiocarbonyl (such as thioester, thioacetate or thiocarbamate), alkoxy, phosphoryl, phosphate, phosphonate, hypophosphonate, amino (e.g., quaternized amino), amide, amidine, imine, cyano, nitro, azide, mercapto, alkylthio, sulfate, sulfonate, aminosulfonyl, sulfonylamino, sulfonyl, heterocyclic, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl and combinations thereof.

[0110] The term "sulfinyl" is represented by the following formula.

[0111]

[0112] Where E is absent, or E is a substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, wherein, independent of E, R represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl. Alkyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, hydroxyl, alkoxy, phosphonium, phosphonyl, silyl, thiol, amide, amino, or -(CH2). m -R”', or E and R together with their associated S atoms form a heterocycle having 3 to 14 atoms in the ring structure; R”' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, an alkoxy group, a phosphonyl group, an amide group, or an amino group; and m is 0 or an integer from 1 to 8.

[0113] The term "sulfonyl" is represented by the following formula.

[0114]

[0115] Where E is absent, or E is a substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, wherein, independently of E, R represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, hydroxyl, alkoxy, phosphonyl, phosphoalkyl, amide, amino, or -(CH2). m -R”', or E and R together with their associated S atoms form a heterocycle having 3 to 14 atoms in the ring structure; R”' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, an alkoxy group, a phosphonyl group, an amide group, or an amino group; and m is 0 or an integer from 1 to 8.

[0116] The term "substituted sulfonyl" refers to a sulfonyl group in which E, R, or both are independently substituted. Such a substituent can be any of the substituents listed above, such as halogen, azide, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thiocarbamate), alkoxy, phosphonium, phosphoryl, phosphoryl, phosphate, phosphonate, hypophosphonate, amino (e.g., quaternized amino), amide, amidine, imine, cyano, nitro, azide, mercapto, alkylthio, sulfate, sulfonate, aminosulfonyl, sulfonylamino, sulfonyl, heterocyclic, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, polyaryl, polyheteroaryl, and combinations thereof.

[0117] The term "sulfonic acid" refers to a sulfonyl group as defined above, where R is a hydroxyl group, E is absent, or E is a substituted or unsubstituted cycloalkyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, or substituted or unsubstituted heteroaryl.

[0118] The term "sulfate ester" refers to a sulfonyl group as defined above, wherein E is an oxygen, alkoxy, aryloxy, substituted alkoxy, or substituted aryloxy group as defined above, and R is independently a hydroxyl, alkoxy, aryloxy, substituted alkoxy, or substituted aryloxy group as defined above. As will be understood by those skilled in the art, when E is oxygen, sulfate esters cannot be attached to another class of chemicals, for example, to form an oxygen-oxygen bond or other unstable bond.

[0119] The term "sulfonate" refers to a sulfonyl group as defined above, wherein E is an oxygen, alkoxy, aryloxy, substituted alkoxy, or substituted aryloxy group as defined above, and R is independently hydrogen, a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted amino, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted heterocyclic, a substituted or unsubstituted aralkyl, a substituted or unsubstituted alkylaryl, a substituted or unsubstituted arylalkyl, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyheteroaryl, or -(CH2). m -R”', where R”' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, an aryl group, a cycloalkyl ring, a cycloalkenyl ring, a heterocyclic ring, an amide group, an amino group, or a polycyclic ring; and m is an integer from 0 to 8. As will be understood by those skilled in the art, when E is oxygen, sulfonates cannot be attached to another class of chemicals, for example, to form an oxygen-oxygen bond or other unstable bond.

[0120] The term "aminosulfonyl" refers to a sulfonamide represented by the following formula.

[0121]

[0122] Where E is absent, or E is a substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted cycloalkyl, etc.), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, wherein independently of E, R and R' each independently represent hydrogen, substituted or unsubstituted alkyl. Substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted carbonyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, hydroxyl, alkoxy, phosphonium, phosphonyl, amide, amino, or -(CH2). m-R”', or R and R' together with their N atoms form a heterocycle having 3 to 14 atoms in the ring structure; R”' represents a hydroxyl group, a substituted or unsubstituted carbonyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted cycloalkenyl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted polyaryl group, a substituted or unsubstituted polyheteroaryl group, an alkoxy group, a phosphonyl group, an amide group, or an amino group; and m is 0 or an integer from 1 to 8.

[0123] The term "thiol" is used interchangeably and is represented by -SR, where R can be the aforementioned hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted aralkyl (e.g., substituted or unsubstituted alkylaryl, substituted or unsubstituted arylalkyl, etc.), substituted or unsubstituted polyaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted carbonyl, phosphonyl, phosphonyl, amide, amino, alkoxy, oxo, phosphonyl, sulfinyl, or silyl.

[0124] The term "alkathioyl" refers to an alkyl group as defined above, having a sulfur group attached to it. The "alkathioyl" group is represented by -S-alkyl. Representative alkathioyl groups include methylthioyl, ethylthioyl, etc. The term "alkathioyl" also includes cycloalkyl groups having a sulfur group attached to them.

[0125] The term "substituted alkathio" refers to an alkathio group having one or more substituents replacing one or more hydrogen atoms on one or more carbon atoms of the alkathio backbone. Such substituents include, but are not limited to, halogens, azides, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (such as carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (such as thioester, thioacetate, or thiocarbamate), alkoxy, phosphonium, phosphoryl, phosphoryl, phosphate, phosphonate, hypophosphonate, amino (e.g., quaternized amino), amide, amidine, imine, cyano, nitro, azide, mercapto, alkathio, sulfate, sulfonate, aminosulfonyl, sulfonylamino, sulfonyl, heterocyclic, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0126] The term "phenylthio" is recognized in the art and refers to -S-C6H5, i.e., a phenyl group attached to a sulfur atom.

[0127] The term "substituted phenylthio" refers to a phenylthio group as defined above, having one or more substituents replacing hydrogen on one or more carbons of the benzene ring. Such substituents include, but are not limited to, halogens, azides, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (such as carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (such as thioester, thioacetate, or thiocarbamate), alkoxy, phosphonium, phosphonyl, phosphoryl, phosphate, phosphonate, hypophosphonate, amino (e.g., quaternized amino), amide, amidine, imine, cyano, nitro, azide, mercapto, alkylthio, sulfate, sulfonate, aminosulfonyl, sulfonylamino, sulfonyl, heterocyclic, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0128] "Arylthio" refers to -S-aryl or -S-heteroaryl, where aryl and heteroaryl are as defined herein.

[0129] The term "substituted arylthio" refers to a -S-aryl or -S-heteroaryl group having one or more substituents replacing hydrogen atoms on one or more ring atoms of an aryl or heteroaryl ring as defined herein. Such substituents include, but are not limited to, halogens, azides, alkyl, aralkyl, alkenyl, alkynyl, cycloalkyl, hydroxyl, carbonyl (e.g., carboxyl, alkoxycarbonyl, formyl, or acyl), silyl, ether, ester, thiocarbonyl (e.g., thioester, thioacetate, or thiocarbamate), alkoxy, phosphonium, phosphonyl, phosphoryl, phosphate, phosphonate, hypophosphonate, amino (e.g., quaternized amino), amide, amidine, imine, cyano, nitro, azide, mercapto, alkylthio, sulfate, sulfonate, aminosulfonyl, sulfonylamino, sulfonyl, heterocyclic, alkylaryl, haloalkyl, -CN, aryl, heteroaryl, and combinations thereof.

[0130] Any range of numerical values ​​disclosed herein independently discloses every possible numerical value that such a range can reasonably cover, as well as any subranges and combinations of subranges covered therein.

[0131] II. Composition

[0132] This paper describes Pt(II) complexes that can emit in the red and / or deep red light regions. The Pt(II) complexes may contain a binuclear center and bidentate and / or tetradentate ligands. These can exhibit red to deep red light emission, with emission maxima spanning 600 nm to 1000 nm (preferably 600 nm to 730 nm) and high emission quantum yields. For example, the Pt(II) complexes disclosed herein exhibit emission maxima in the 600 nm to 730 nm range and have high room-temperature emission quantum yields (up to 80%), measured by absolute measurement methods or relative measurement methods using standard references such as Pt(tpdbp), and short emission lifetimes (as low as 1.3 μs), as measured by absolute measurement methods or relative measurement methods using standard references such as Pt(tpdbp).

[0133] Unbound by any theory, these binuclear Pt(II) complexes possess ~ Tight Pt-Pt contact and below The close interplanar spacing. This dual-core feature can enhance the... 3 The metallic properties of the MMLCT (metal-metal-ligand charge transfer) excited states lead to the high stability, high emission quantum yield, and high radiative decay rate (approximately 10^6) of these Pt(II) complexes. 5 s -1 Such a high rate of radiative decay exceeds the increased rate of non-radiative decay typically observed in red light emitters.

[0134] A. Platinum(II) complex

[0135] This platinum(II) complex can have the structure of formula I':

[0136]

[0137] Wherein: (a) the compound may have an overall neutral charge, negative charge, or positive charge; (b) CY1, CY2, CY3, and CY4 may independently be substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, or substituted or unsubstituted cycloalkynyl; (c) R1, R2, R3, and R4 may independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkynyl, or substituted or unsubstituted cycloalkynyl. (d) n1, n2, n3 and n4 may independently be integers from 0 to 10; (e) L1 and L3 may independently be bonds (single, double or triple), absent, oxygen, sulfur, amino, amide, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, carbonyl, sulfonyl, sulfonic acid, phosphoryl or phosphonyl; (f) R5, R6, R7 and R8 may independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted alkyl ... (g) L2 and L4 can independently be bonds (single, double, or triple), substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, amino, amide, or carbonyl; (h) may be absent, bonds (single, double, or triple), substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heterocyclic, alkoxy, aryloxy, ether, Polyether, sulfonyl, or thioether; and (i) the substituent may independently be a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclic, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyhexaaryl, a substituted or unsubstituted aralkyl, a substituted or unsubstituted carbonyl, a substituted or unsubstituted alkoxy, halogen, hydroxyl, phenoxy, aryloxy, alkylthio, phenylthio, arylthio, cyano, isocyano, nitro, carboxyl, amino, amide, oxo, silyl, sulfinyl, sulfonyl, sulfonic acid, phosphonium, phosphonyl, phosphoryl, phosphonyl, or thiol, or a combination thereof.

[0138] In some forms, the platinum(II) complex may have the structure of formula I or I”:

[0139]

[0140] Wherein: (a) the compound may have an overall neutral charge, negative charge, or positive charge; (b) CY1, CY2, CY3, and CY4 may independently be substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, or substituted or unsubstituted cycloalkynyl; (c) R1, R2, R3, and R4 may independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted cycloalkynyl, or substituted or unsubstituted cycloalkynyl. (d) n1, n2, n3 and n4 may independently be integers from 0 to 10; (e) L1 and L3 may independently be bonds (single, double or triple), absent, oxygen, sulfur, amino, amide, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, carbonyl, sulfonyl, sulfonic acid, phosphoryl or phosphonyl; (f) R5, R6, R7 and R8 may independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted alkyl ... (g) L2 and L4 can independently be bonds (single, double, or triple), substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, amino, amide, or carbonyl; (h) may be absent, bonds (single, double, or triple), substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heterocyclic, alkoxy, aryloxy, ether, Polyether, sulfonyl, or thioether; and (i) the substituent may independently be a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclic, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyhexaaryl, a substituted or unsubstituted aralkyl, a substituted or unsubstituted carbonyl, a substituted or unsubstituted alkoxy, halogen, hydroxyl, phenoxy, aryloxy, alkylthio, phenylthio, arylthio, cyano, isocyano, nitro, carboxyl, amino, amide, oxo, silyl, sulfinyl, sulfonyl, sulfonic acid, phosphonium, phosphonyl, phosphoryl, phosphonyl, or thiol, or a combination thereof.

[0141] In some forms, the platinum(II) complex is an isomer having the structure of formula Ia, Ia', Ib, or Ib':

[0142]

[0143]

[0144] Wherein CY1, CY2, CY3, CY4, R1, R2, R3, R4, n1, n2, n3, n4, L1, L3, R5, R6, R7, R8, L2, L4, ------ and the substituents can be defined as in Formula I above.

[0145] In some forms of formula I, I', I”, Ia, Ia', Ib and / or Ib', the platinum(II) complex may have an overall neutral charge. In some forms of formula I, Ia and / or Ib, CY1, CY2, CY3 and CY4 may be independently substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, or substituted or unsubstituted heterocyclic group.

[0146] In some forms, the platinum(II) complex may have the structure of formula II or II':

[0147]

[0148]

[0149] Wherein: (a) CY2 and CY3 can be independently substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, or substituted or unsubstituted cycloynyl; (b) R2 and R3 can be independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, or substituted or unsubstituted polyheteroaryl. (c) n2, n3, n5 and n6 may independently be integers from 0 to 10; (d) R5, R6, R7 and R8 may independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, alkoxy or aryloxy; (e) R9 and R 10It can be independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol; (f)R 11 -R 14 and R 21 -R 24 It can independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol, and optionally, R 11 and R 12 Together, R 12 and R 13 Together, R 13 and R 14 Together, R 21 and R 22 Together, R 22 and R 23 Together and / or R 23 and R 24 Together they can form substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkynyl, or substituted or unsubstituted heterocyclic, such as substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; (g) G1' and G2' can be C or N independently; (h) ------ can be absent, bond (single, double or triple bond), substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, alkoxy, aryloxy, ether, polyether, sulfonyl or thioether; and (i) the substituents can be as defined above for Formula I.

[0150] In some forms, the platinum(II) complex is an isomer having the structure of formula IIa, IIa', IIb or IIb':

[0151]

[0152] Among them, CY2, CY3, R2, R3, n2, n3, n5, n6, R5-R8, and R9-R14 R 21 -R 24 G1' and G2', and the substituents can be defined as in Formula II above.

[0153] In some forms of formulas I, I', I”, Ia, Ia', Ib, Ib', II, II', IIa, IIa', IIb and / or IIb', CY2 and CY3 may independently be substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, or substituted or unsubstituted heterocyclic. In some forms of formulas I, I', I”, Ia, Ia', Ib, Ib', II, II', IIa, IIa', IIb and / or IIb', n2 and n3 are independently integers from 2 to 4, and two adjacent R2 and / or two adjacent R3 form a substituted or unsubstituted aryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted heterocyclic, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted cycloalkenyl, or a substituted or unsubstituted cycloynyl.

[0154] In some forms, the platinum(II) complex may have the structure of formula III' or III”:

[0155]

[0156] Wherein: (a) R5, R6, R7 and R8 may independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, alkoxy or aryloxy; (b) R9 and R 10 It can be independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol; (c)R 11 -R 14 and R 21 -R 24 It can independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol, and optionally, R 11 and R12 Together, R 12 and R 13 Together, R 13 and R 14 Together, R 21 and R 22 Together, R 22 and R 23 Together and / or R 23 and R 24 Together they can form substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkynyl, or substituted or unsubstituted heterocyclic, such as substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; (d) each can independently be absent, bond (single, double or triple bond), substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, alkoxy, aryloxy, ether, polyether, sulfonyl or thioether; (e) X1', X2', Y1'-Y8' can independently be O, S, CR 15 or NR 18 R 15 and R 18 It can be independently absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro or thiol; and (f) the substituent can be as defined above for Formula I.

[0157] In some forms, the platinum(II) complex may have the structure of formula III or III”':

[0158]

[0159]

[0160] Wherein: (a) R5, R6, R7 and R8 may independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, alkoxy or aryloxy; (b) R9 and R 10It can be independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol; (c)R 11 -R 14 R 16 R 17 and R 19 -R 24 It can independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol, and optionally, R 11 and R 12 Together, R 12 and R 13 Together, R 13 and R 14 Together, R 16 and R 17 Together, R 19 and R 20 Together, R 21 and R 22 Together, R 22 and R 23 Together and / or R 23 and R 24 Together they can form substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkynyl, or substituted or unsubstituted heterocyclic, such as substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; (d) each can independently be absent, bond (single, double or triple bond), substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, alkoxy, aryloxy, ether, polyether, sulfonyl or thioether; (e) X1', X2', Y1', Y2', Y3' and Y4' can independently be O, S, CR 15 or NR 18 R 15 and R 18It can be independently absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro or thiol; and (f) the substituent can be as defined above for Formula I.

[0161] In some forms, the platinum(II) complex is an isomer having the structure of formula IIIa, IIIa', IIIb, or IIIb':

[0162]

[0163]

[0164] Among them, R5-R 24 , ------, X1', X2', Y1', Y2', Y3', Y4' and substituents can be defined as in Formula III above.

[0165] In some forms of equations III, III', III”, III”', IIIa, IIIa', IIIb and / or IIIb', X1', X2', Y1', Y2', Y3' and Y4' can be independently CR 15 or NR 18 R 15 and R 18 It can be independently absent, hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. In some forms of formulas III, III', IIIa and / or IIIb, X1', X2', Y1' and / or Y3' and Y2' and / or Y4' can be independently NR. 18 R 18 Each occurrence of R can be absent, hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. In some forms of formulas III, III', III”, III”', IIIa, IIIa', IIIb and / or IIIb', R 16 R 17 R 19 and R 20 It can be independently hydrogen, halogen, nitrile, nitro, amino, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, or hydroxyl, or R. 16 and R 17 R 19 and R 20 R 22and R 23 and / or R 12 and R 13 Together they form substituted or unsubstituted aryl groups, substituted or unsubstituted polyaryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted polyheteroaryl groups, substituted or unsubstituted heterocyclic groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted cycloalkenyl groups, or substituted or unsubstituted cycloynyl groups. In some forms of formulas III, III', III”, III”', IIIa, IIIa', IIIb and / or IIIb', R 16 and R 17 and / or R 19 and R 20 Together they form substituted or unsubstituted aryl groups, substituted or unsubstituted polyaryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted polyheteroaryl groups, substituted or unsubstituted heterocyclic groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted cycloalkenyl groups, or substituted or unsubstituted cycloynyl groups. In some forms of formulas III, III', III”, III”', IIIa, IIIa', IIIb and / or IIIb', R 12 and R 13 and / or R 22 and R 23 Together they form substituted or unsubstituted aryl groups, substituted or unsubstituted polyaryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted polyheteroaryl groups, substituted or unsubstituted heterocyclic groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted cycloalkenyl groups, or substituted or unsubstituted cycloynyl groups.

[0166] In some forms, the platinum(II) complex may have the structure of formula IV or IV':

[0167]

[0168] Wherein: (a) R5, R6, R7 and R8 may independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, alkoxy or aryloxy; (b) R9 and R 10 It can be independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol; (c)R 11 -R 14 R 21 -R24 and R 27 -R 34 It can independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol, and optionally, R 11 and R 12 Together, R 12 and R 13 Together, R 13 and R 14 Together, R 21 and R 22 Together, R 22 and R 23 Together, R 23 and R 24 R 27 and R 28 Together, R 28 and R 29 Together, R 29 and R 30 Together, R 31 and R 32 Together, R 32 and R 33 Together and / or R 33 and R 34 Together they can form substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkynyl, or substituted or unsubstituted heterocyclic, such as substituted or unsubstituted cycloalkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl; (d) each can independently be absent, bond (single, double or triple bond), substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, alkoxy, aryloxy, ether, polyether, sulfonyl or thioether; (e) X3' and X4' can independently be CR 25 or NR 26 R 25 and R 26It can be independently absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro or thiol; and (f) the substituent can be as defined above for Formula I.

[0169] In some forms, the platinum(II) complex is an isomer having the structure of formula IVa, IVa', IVb, or IVb':

[0170]

[0171]

[0172] Among them, R5-R 24 R 27 -R 34 , ------, X3', X4' and substituents can be defined as in formula IV above.

[0173] In some forms of equations IV, IV', IVa, IVa', IVb and / or IVb', X3' and X4' can be independently CR 25 or NR 26 R 25 and R 26 It can be independently absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl. In some forms of formula IV, IVa and / or IVb, X3' and X4' can be independently NR. 26 R 26 Each occurrence of R can independently be absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl. In some forms of formulas IV, IV', IVa, IVa', IVb and / or IVb', R 27 -R 34 It can be independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, or hydroxyl. In some forms of formulas IV, IV', IVa, IVa', IVb, and / or IVb', R 27 -R 34 It can be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, independently.

[0174] In some forms of equations II, II', IIa, IIa', IIb, IIb', III, III', III”, III”', IIIa, IIIa', IIIb, IIIb', IV, IV', IVa, IVa', IVb and / or IVb', R9 and R 10 It can be hydrogen or a substituted or unsubstituted alkyl group independently. In some forms of formulas II, II', IIa, IIa', IIb, IIb', III, III', III”, III”', IIIa, IIIa', IIIb, IIIb', IV, IV', IVa, IVa', IVb and / or IVb', R 11 -R 14 and R 21 -R 24 It can independently be hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, hydroxyl, alkoxy, or aryloxy. In some forms of formulas II, II', IIa, IIa', IIb, IIb', III, III', III”, III”', IIIa, IIIa', IIIb, IIIb', IV, IV', IVa, IVa', IVb, and / or IVb', R 11 R 12 R 21 R 22 It can be hydrogen, or R 11 and R 12 Together they can form substituted or unsubstituted heteroaryl groups, substituted or unsubstituted polyheteroaryl groups, or substituted or unsubstituted heterocyclic groups, and / or R 21 and R 22 Together they can form substituted or unsubstituted heteroaryl groups, substituted or unsubstituted polyaryl groups, or substituted or unsubstituted heterocyclic groups.

[0175] In some forms of equations II, II', IIa, IIa', IIb, IIb', III, III', III”, III”', IIIa, IIIa', IIIb, IIIb', IV, IV', IVa, IVa', IVb and / or IVb', R 11 R 12 R 21 R 22 It can be hydrogen, or R 11 and R 12 Together they can form and / or R 21 and R 22 Together they can form a structure of form V:

[0176]

[0177] Where: (a) Z' can be O, S, or CR 39 or NR 40 R 39 and R 40 (a) J1' and J2' can independently be absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol; (b) J1' and J2' can independently be R 41 and R 42 (c) n7 can be independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol, and optionally, J1' and J2' together can form a substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, or substituted or unsubstituted cycloalkynyl; and (d) R 35 -R 38 It can be independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro or thiol.

[0178] In some forms of equation V, n7 can be 0, and Z' can be O, S, or NR. 40 R 40 Each occurrence of R can independently be hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heterocyclic group, or a hydroxyl group. In some forms of formula V, R 35 -R 38 It can be independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, or substituted or unsubstituted heterocyclic, hydroxyl, alkoxy or aryloxy.

[0179] In some forms of Formula V, J1' and J2' together can form a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted cycloalkenyl, or a substituted or unsubstituted cycloynyl, such as an unsubstituted cycloalkyl, an unsubstituted cycloalkenyl, or an unsubstituted cycloynyl, for example, an unsubstituted cycloalkyl. The cycloalkyl, cycloalkenyl, and cycloynyl groups of Formula V can be monocyclic or polycyclic, such as C3-C4. 30 C4-C 30 C4-C 25 C4-C 20 C4-C 18 C4-C 16 C4-C 15 C4-C 14 C4-C 13 C4-C 12 C4-C 10 Cycloalkyl, cycloalkenyl, or cycloynyl groups, belonging to the C4-C9, C4-C8, C4-C7, C4-C6, or C4-C5 monocyclic or polycyclic groups. For example, J1' and J2' together can form monocyclic or polycyclic alkyl groups as shown below:

[0180]

[0181] In some forms, the platinum(II) complex may contain one or two tetradentate ligands, each tetradentate replacing two bidentate bridging ligands. The inclusion of tetradentate ligands in these platinum(II) complexes allows for subtle structural refinement. For example, replacing two bidentate bridging ligands with one tetradentate bridging ligand in these Pt(II) complexes narrows the full width at half maximum (FWHM) of the emission profile by approximately 30 nm while maintaining the coordination framework and other photophysical properties, such as a shortened emission lifetime.

[0182] In some forms of formulas I, I', I”, Ia, Ia', Ib, Ib', II, II', IIa, IIa', IIb, IIb', III, III', III”, III”', IIIa, IIIa', IIIb, IIIb', IV, IV', IVa, IVa', IVb', IVb and / or IVb', any one of the following—between R5 and R8, between R6 and R7, between R5 and R7, and between R6 and R8—may be absent, a single bond, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted... Substituted heteroaryl groups, substituted or unsubstituted polyheteroaryl groups, substituted or unsubstituted heterocyclic groups, alkoxy groups, aryloxy groups, ethers, polyethers, sulfonyl groups, or thioethers. In some forms, at least one is absent, allowing the platinum(II) complex to contain one or two tetradentate ligands, each tetradentate ligand replacing two bidentate bridging ligands. The inclusion of tetradentate ligands in these platinum(II) complexes achieves subtle structural refinement. For example, replacing two bidentate bridging ligands with one tetradentate bridging ligand in these Pt(II) complexes narrows the full width at half maximum (FWHM) of the emission profile by approximately 30 nm while maintaining the coordination framework and other photophysical properties, such as a shortened emission lifetime.

[0183] In some forms of equations I, I', I”, Ia, Ia', Ib, Ib', II, II', IIa, IIa', IIb, IIb', III, III', III”, III”', IIIa, IIIa', IIIb, IIIb', IV, IV', IVa, IVa', IVb and / or IVb', Each of them can have a structure: Wherein: (a) A' and B' may independently be substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloalkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, or substituted or unsubstituted heterocyclic, such as substituted or unsubstituted aryl; and (b) each occurrence of L5 may independently be an ether, polyether, alkoxy, thioether, sulfonyl, substituted or unsubstituted heterocyclic, substituted or unsubstituted aryl, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, or substituted or unsubstituted alkynyl. In some forms, A' and B' may independently be substituted or unsubstituted aryl or substituted or unsubstituted polyaryl; and L5 may have the following structure: Where: (a) Q1' and Q2' can be independent of being non-existent, O or S; and (b) n9 can be an integer from 1 to 10, such as 1 to 6, for example 1, 2 or 6.

[0184] In some forms of formulas I, I', I”, Ia, Ia', Ib, Ib', II, II', IIa, IIa', IIb, IIb', III, III', III”, III”', IIIa, IIIa', IIIb, IIIb', IV, IV', IVa, IVa', IVb', IVb and / or IVb', the substituent of the substituted functional group may be a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclic, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyheteroaryl, a substituted or unsubstituted aralkyl, carbonyl, alkoxy, aryloxy, amino, amide or hydroxyl, or a combination thereof.

[0185] In some forms of formulas I, I', I”, Ia, Ia', Ib, Ib', II, II', IIa, IIa', IIb, IIb', III, III', III”, III”', IIIa, IIIa', IIIb, IIIb', IV, IV', IVa, IVa', IVb and / or IVb', the substituent of the substituted functional group may be an unsubstituted alkyl, unsubstituted alkenyl, unsubstituted alkynyl, unsubstituted heterocyclic, unsubstituted aryl, unsubstituted heteroaryl, unsubstituted aralkyl, carboxyl, ester, thioester, hydroxyl, alkoxy, amino or amide, or a combination thereof.

[0186] In some forms of formulas I, I', I”, Ia, Ia', Ib, Ib', II, II', IIa, IIa', IIb, IIb', III, III', III”, III”', IIIa, IIIa', IIIb, IIIb', IV, IV', IVa, IVa', IVb', IVb and / or IVb', the alkyl group can be a straight-chain alkyl group, a branched alkyl group, or a cyclic alkyl group (monocyclic or polycyclic). Exemplary alkyl groups include straight-chain C1-C1 alkyl groups. 30 Alkyl, branched C4-C 30 Alkyl, cyclic C3-C 30 Alkyl, straight-chain C1-C 20 Alkyl, branched C4-C 20 Alkyl, cyclic C3-C 20 Alkyl, straight-chain C1-C 10 Alkyl, branched C4-C 10 Alkyl, cyclic C3-C 10 Alkyl, straight-chain C1-C6 alkyl, branched-chain C4-C6 alkyl, cyclic C3-C6 alkyl, straight-chain C1-C4 alkyl, cyclic C3-C4 alkyl, such as straight-chain C1-C6 alkyl 10C1-C9, C1-C8, C1-C7, C1-C6, C1-C5, C1-C4, C1-C3, C1-C2 alkyl groups; branched C3-C9, C3-C9, C3-C8, C3-C7, C3-C6, C3-C5, C3-C4 alkyl groups; or cyclic C3-C9, C3-C9, C3-C8, C3-C7, C3-C6, C3-C5, C3-C4 alkyl groups. Cyclic alkyl groups can be monocyclic or polycyclic, such as C3-C... 30 C4-C 30 C4-C 25 C4-C 20 C4-C 18 C4-C 16 C4-C 15 C4-C 14 C4-C 13 C4-C 12 C4-C 10 C4-C9, C4-C8, C4-C7, C4-C6, or C4-C5 monocyclic or polycyclic alkyl groups.

[0187] In some forms of formulas I, I', I”, Ia, Ia', Ib, Ib', II, II', IIa, IIa', IIb, IIb', III, III', III”, III”', IIIa, IIIa', IIIb, IIIb', IV, IV', IVa, IVa', IVb and / or IVb', the alkenyl group can be a straight-chain alkenyl, a branched alkenyl, or a cyclic alkenyl (monocyclic or polycyclic). Exemplary alkenyl groups include straight-chain C1-C 30 Alkenyl, branched C4-C 30 Alkenyl, cyclic C3-C 30 Alkenyl, straight-chain C1-C 20 Alkenyl, branched C4-C 20 Alkenyl, cyclic C3-C 20 Alkenyl, straight-chain C1-C 10 Alkenyl, branched C4-C 10 Alkenyl, cyclic C3-C 10 Alkenyl, straight-chain C1-C6 alkenyl, branched-chain C4-C6 alkenyl, cyclic C3-C6 alkenyl, straight-chain C1-C4 alkenyl, cyclic C3-C4 alkenyl, such as straight-chain C1-C6 alkenyl. 10C1-C9, C1-C8, C1-C7, C1-C6, C1-C5, C1-C4, C1-C3, C1-C2 alkenyl groups; branched C3-C9, C3-C9, C3-C8, C3-C7, C3-C6, C3-C5, C3-C4 alkenyl groups; or cyclic C3-C9, C3-C9, C3-C8, C3-C7, C3-C6, C3-C5, C3-C4 alkenyl groups. Cyclic alkenyl groups can be monocyclic or polycyclic, such as C3-C... 30 C4-C 30 C4-C 25 C4-C 20 C4-C 18 C4-C 16 C4-C 15 C4-C 14 C4-C 13 C4-C 12 C4-C 10 C4-C9, C4-C8, C4-C7, C4-C6, or C4-C5 monocyclic or polycyclic alkenyl groups.

[0188] In some forms of formulas I, I', I”, Ia, Ia', Ib, Ib', II, II', IIa, IIa', IIb, IIb', III, III', III”, III”', IIIa, IIIa', IIIb, IIIb', IV, IV', IVa, IVa', IVb', IVb and / or IVb', the alkynyl group can be a straight-chain alkynyl, a branched-chain alkynyl, or a cyclic alkynyl (monocyclic or polycyclic). Exemplary alkynyl groups include straight-chain C1-C 30 Alkyne group, branched C4-C 30 Alkyne group, cyclic C3-C 30 Alkyne group, straight-chain C1-C 20 Alkyne group, branched C4-C 20 Alkyne group, cyclic C3-C 20 Alkyne group, straight-chain C1-C 10 Alkyne group, branched C4-C 10 Alkyne group, cyclic C3-C 10 Alkynyl, straight-chain C1-C6 alkynyl, branched-chain C4-C6 alkynyl, cyclic C3-C6 alkynyl, straight-chain C1-C4 alkynyl, cyclic C3-C4 alkynyl, such as straight-chain C1-C 10C1-C9, C1-C8, C1-C7, C1-C6, C1-C5, C1-C4, C1-C3, C1-C2 alkynyl groups; branched C3-C9, C3-C9, C3-C8, C3-C7, C3-C6, C3-C5, C3-C4 alkynyl groups; or cyclic C3-C9, C3-C9, C3-C8, C3-C7, C3-C6, C3-C5, C3-C4 alkynyl groups. Cyclic alkynyl groups can be monocyclic or polycyclic, such as C3-C... 30 C4-C 30 C4-C 25 C4-C 20 C4-C 18 C4-C 16 C4-C 15 C4-C 14 C4-C 13 C4-C 12 C4-C 10 C4-C9, C4-C8, C4-C7, C4-C6, or C4-C5 monocyclic or polycyclic alkynyl groups.

[0189] It should be understood that any exemplary alkyl, alkenyl, and ynyl group can be a heteroalkyl, heteroalkenyl, and heteroynyl group, respectively. For example, the alkyl group can be a straight-chain C2-C group. 30 Heteroalkyl, branched C4-C 30 Heteroalkyl, cyclic C3-C 30 Heteroalkyl (i.e., heterocyclic alkyl), straight-chain C1-C 20 Heteroalkyl, branched C4-C 20 Heteroalkyl, cyclic C3-C 20 Heteroalkyl, straight-chain C1-C 10 Heteroalkyl, branched C4-C 10 Heteroalkyl, cyclic C3-C 10 Heteroalkyl, straight-chain C1-C6 heteroalkyl, branched-chain C4-C6 heteroalkyl, cyclic C3-C6 heteroalkyl, straight-chain C1-C4 heteroalkyl, cyclic C3-C4 heteroalkyl, such as straight-chain C1-C 10 C1-C9, C1-C8, C1-C7, C1-C6, C1-C5, C1-C4, C1-C3, C1-C2 heteroalkyl groups; branched C3-C9, C3-C9, C3-C8, C3-C7, C3-C6, C3-C5, C3-C4 heteroalkyl groups; or cyclic C3-C9, C3-C9, C3-C8, C3-C7, C3-C6, C3-C5, C3-C4 heteroalkyl groups. Cyclic heteroalkyl groups can be monocyclic or polycyclic, such as C3-C... 30 C4-C 30 C4-C 25 C4-C 20 C4-C18 C4-C 16 C4-C 15 C4-C 14 C4-C 13 C4-C 12 C4-C 10 C4-C9, C4-C8, C4-C7, C4-C6, or C4-C5 monocyclic or polycyclic heteroalkyl groups.

[0190] For example, the alkenyl group can be a straight-chain C2-C 30 Heteroalkenyl, branched C4-C 30 Heteroalkenyl, cyclic C3-C 30 Heteroalkenyl (i.e., heterocyclic alkenyl), straight-chain C1-C 20 Heteroalkenyl, branched C4-C 20 Heteroalkenyl, cyclic C3-C 20 Heteroalkenyl, straight-chain C1-C 10 Heteroalkenyl, branched C4-C 10 Heteroalkenyl, cyclic C3-C 10 heteroalkenyl, straight-chain C1-C6 heteroalkenyl, branched-chain C4-C6 heteroalkenyl, cyclic C3-C6 heteroalkenyl, straight-chain C1-C4 heteroalkenyl, cyclic C3-C4 heteroalkenyl, such as straight-chain C1-C 10 C1-C9, C1-C8, C1-C7, C1-C6, C1-C5, C1-C4, C1-C3, C1-C2 heteroalkenyl groups; branched C3-C9, C3-C9, C3-C8, C3-C7, C3-C6, C3-C5, C3-C4 heteroalkenyl groups; or cyclic C3-C9, C3-C9, C3-C8, C3-C7, C3-C6, C3-C5, C3-C4 heteroalkenyl groups. Cyclic heteroalkenyl groups can be monocyclic or polycyclic, such as C3-C... 30 C4-C 30 C4-C 25 C4-C 20 C4-C 18 C4-C 16 C4-C 15 C4-C 14 C4-C 13 C4-C 12 C4-C 10 C4-C9, C4-C8, C4-C7, C4-C6, or C4-C5 monocyclic or polycyclic heteroene groups.

[0191] For example, the alkynyl group can be a straight-chain C2-C 30 Heterynyl group, branched C4-C 30 Heterynyl, cyclic C3-C 30 heterocyclic ynyl group (i.e., heterocyclic ynyl group), straight-chain C1-C20 Heterynyl group, branched C4-C 20 Heterynyl, cyclic C3-C 20 Heterynyl, straight-chain C1-C 10 Heterynyl group, branched C4-C 10 Heterynyl, cyclic C3-C 10 Xyrynyl, straight-chain C1-C6 xyrynyl, branched C4-C6 xyrynyl, cyclic C3-C6 xyrynyl, straight-chain C1-C4 xyrynyl, cyclic C3-C4 xyrynyl, such as straight-chain C1-C 1o C1-C9, C1-C8, C1-C7, C1-C6, C1-C5, C1-C4, C1-C3, C1-C2 heteroynyl groups; branched C3-C9, C3-C9, C3-C8, C3-C7, C3-C6, C3-C5, C3-C4 heteroynyl groups; or cyclic C3-C9, C3-C9, C3-C8, C3-C7, C3-C6, C3-C5, C3-C4 heteroynyl groups. Cyclic heteroynyl groups can be monocyclic or polycyclic, such as C3-C... 30 C4-C 30 C4-C 25 C4-C 20 C4-C 18 C4-C 16 C4-C 15 C4-C 14 C4-C 13 C4-C 12 C4-C 10 C4-C9, C4-C8, C4-C7, C4-C6, or C4-C5 monocyclic or polycyclic heteroyne groups.

[0192] For example, the aryl group can be C5-C. 30 Aryl, C5-C 20 Aryl, C s -C 12 Aryl, C5-C 11 Aryl, C5-C9 aryl, C6-C 20 Aryl, C6-C 12 Aryl, C6-C 11 Aryl or C6-C9 aryl. It's important to understand that aryl can be heteroaryl, such as C5-C9. 30 heteroaryl, C5-C 20 heteroaryl, C5-C 12 heteroaryl, C5-C 11 heteroaryl, C5-C9 heteroaryl, C6-C 30 heteroaryl, C6-C 20 heteroaryl, C6-C 12 heteroaryl, C6-C 11Heteroaryl or C6-C9 heteroaryl. Polyaryl groups can be C... 10 -C 30 Polyaryl, C 10 -C 20 Polyaryl, C 10 -C 12 Polyaryl, C 10 -C 11 Polyaryl or C 12 -C 20 Polyaryl. It's important to understand that aryl groups can be polyheteroaryl, such as C... 10 -C 30 Polyarylene, C 10 -C 20 Polyarylene, C 10 -C 12 Polyarylene, C 10 -C 11 Polyarylene or C 12 -C 20 Multi-aryl aromatics.

[0193] Pt(II) complexes may contain one or more chiral centers, or may otherwise exist as a variety of stereoisomers. These can be pure (single) stereoisomers or mixtures of stereoisomers, such as enantiomers, diastereomers, and mixtures enriched with enantiomers or diastereomers. Pt(II) complexes can exist as geometric isomers. Therefore, it is to be understood that the present invention includes pure geometric isomers or mixtures of geometric isomers.

[0194] 2. Exemplary platinum(II) complexes

[0195] The following shows an exemplary Pt(II) complex.

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203] 3. Photophysical properties

[0204] The photophysical properties of Pt(II) complexes can be determined by their emission lifetime (“τ”).em (or "τ"), radiation decay rate ("kr"), emission quantum yield ("QY" or "Φ") em ”), maximum emission wavelength (“λ”) max Evaluation of τ and / or full width at half maximum ("FWHM"). τ of platinum(II) complexes was measured. em ,kr,QY,λ max The techniques of FWHM are known. For example, these parameters can be obtained by measuring the emission spectrum of platinum(II) complexes. For example, based on the measured emission spectrum, the τ of the platinum(II) complex... em The following methods can be used to obtain the emission decay intensity over time using a Quanta Ray GCR 150-10 pulsed Nd:YAG laser system (pulse output: 355 nm), and (ii) to determine τ by fitting the exponential decay of formula (1) using Origin software. em Where I0 is the initial emission intensity, I(t) is the emission intensity at time t, τ is the emission lifetime, and t is time.

[0205] I(t) = I0e …t / τ Formula (1)

[0206] platinum(II) complex k r k can be used r =Φ em / τ em Obtained. Φ of these Pt complexes em The value can be measured by known methods, such as direct measurement or relative methods. For example, the Φ of the disclosed Pt(II) complex in solution or thin film can be obtained directly by absolute measurement using a Hamamatsu C11347Quantaurus-QY Absolute PL quantum yield spectrometer (PL stands for photoluminescence). em For example, Pt(tpdbp) can be used as a standard reference (Φ). r : 0.51, λ em The relative method for measuring the Pt(II) complex in the near-infrared (“NIR”) region (i.e., λ = 770 nm) was used to measure the Pt(II) complex in the near-infrared (“NIR”) region (i.e., λ = 770 nm). max Solutions in the range of 700 nm to approximately 1000 nm Φ em Such as complex 4a(λ) max =753 (max) (903nm). In the relative method, Φ em It can be solved by the equation: Φ em =Φ r (B r / B s )(n s / nr ) 2 (D s / D r ) Calculate, where r and s represent the sample and reference standard, respectively, and B = 1-10 -AL Where A is the absorbance at the excitation wavelength, L is the optical path length in cm, n is the refractive index of the solvent, and D is the integrated emission intensity.

[0207] λ of platinum(II) complex max Both FWHM and FWHM can be directly measured by emission spectroscopy.

[0208] In some forms, the platinum(II) complex of any one of formulas I-IV may have an emission lifetime (τ) of up to 3.0 μs, up to 2.5 μs, up to 2.0 μs, 0.5 μs to 3.0 μs, 0.8 μs to 3.0 μs, 1.0 μs to 3.0 μs, 0.5 μs to 2.5 μs, 0.8 μs to 2.5 μs, 1.0 μs to 2.5 μs, 0.5 μs to 2.0 μs, 0.8 μs to 2.0 μs, or 1.0 μs to 2.0 μs, obtained, for example, based on the emission spectrum of the platinum(II) complex as described above, in solution or in a film. em ).

[0209] In some forms, the platinum(II) complex of any one of formulas I-IV may have an emission spectrum of at least 1.0 x 10⁻⁶ in solution or in a membrane, for example, based on the emission spectrum of the platinum(II) complex as described above. 5 s -1 At least 1.4x10 5 s -1 1.0x10 5 s -1 Up to 25.0x10 5 s -1 1.0x10 5 s -1 Up to 20.0x10 5 s -1 1.0x10 5 s -1 Up to 15.0x10 5 s -1 1.0x10 5 s -1 Up to 12.0x10 5 s -1 1.0x10 5 s -1 Up to 10.0x10 5 s -1 1.0x10 5 s -1 Up to 8.0x105 s -1 1.0x10 5 s -1 Up to 6.0x10 5 s -1 1.4x10 5 s -1 Up to 25.0x10 5 s -1 1.4x10 5 s -1 Up to 20.0x10 5 s -1 1.4x10 5 s -1 Up to 15.0x10 5 s -1 1.4x10 5 s -1 Up to 12.0x10 5 s -1 1.4x10 5 s -1 Up to 10.0x10 5 s -1 1.4x10 5 s -1 Up to 8.0x10 5 s -1 or 1.4x10 5 s -1 Up to 6.0x10 5 s -1 Radiative attenuation rate (k r ).

[0210] In some forms, the platinum(II) complex of any one of formulas I-IV may have an emission quantum yield (“QY” or “Φ”) of at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, 50% to 90%, 55% to 90%, 60% to 90%, 50% to 80%, 55% to 80%, or 60% to 80% obtained, for example, based on the emission spectrum of the platinum(II) complex as described above, in solution or in a membrane at room temperature. em ”).

[0211] In some forms, the platinum(II) complex of any one of formulas I-IV may have a maximum emission wavelength ("λ") of 600 nm to 1000 nm, 600 nm to 760 nm, 600 nm to 735 nm, 604 nm to 733 nm, 600 nm to 700 nm, 700 nm to 1000 nm, 700 nm to 760 nm, or 704 nm to 760 nm, obtained, for example, based on the emission spectrum of the platinum(II) complex as described above. maxAs used herein, near-infrared (“near IR” or “NIR”) λ max Within the 700nm to 1000nm range, including the endpoints. As used in this paper, red λ... max Within the 600nm to 700nm range, including the endpoints. λ is exactly 700nm. max It can be considered red or near-infrared. However, regarding λ... max In terms of range, 700nm should be considered near-infrared λ. max Still red λ max This can be determined by whether 700nm represents the high-end or low-end segment. This applies to the area spanning between below and above 700nm. max In terms of scope, this scope and the 700nm point can be considered to include both the red λ max It also includes near-infrared λ max .

[0212] In some forms, the platinum(II) complex of any one of formulas I-IV may have, for example, emission spectra of platinum(II) complexes as described above, up to 270 nm, up to 250 nm, up to 220 nm, up to 200 nm, up to 180 nm, up to 160 nm, up to 145 nm, up to 135 nm, up to 120 nm, up to 110 nm, up to 100 nm, up to 90 nm, up to 80 nm, 50 nm to 270 nm, 5 Full width at half maximum ("FWHM") of 0nm to 250nm, 50nm to 220nm, 50nm to 200nm, 50nm to 180nm, 50nm to 160nm, 50nm to 145nm, 50nm to 110nm, 60nm to 270nm, 60nm to 250nm, 60nm to 220nm, 60nm to 200nm, 60nm to 145nm, 70nm to 200nm, or 70nm to 145nm. In some forms, the platinum(II) complex contains one or two [emission spectra] having, for example, a maximum of 240 nm, a maximum of 220 nm, a maximum of 190 nm, a maximum of 170 nm, a maximum of 155 nm, a maximum of 145 nm, a maximum of 135 nm, a maximum of 120 nm, a maximum of 110 nm, a maximum of 100 nm, a maximum of 90 nm, a maximum of 80 nm, 20 nm to 240 nm, 20 nm to 220 nm, 20 nm to 190 nm, 20 nm to 170 nm, 20 nm to 155 nm, 20 nm to 145 nm, and 20 nm to 110 nm. Tetradentate ligands with full width at half maximum ("FWHM") of 20 nm to 100 nm, 30 nm to 240 nm, 30 nm to 220 nm, 30 nm to 190 nm, 30 nm to 170 nm, 30 nm to 155 nm, 30 nm to 145 nm, 30 nm to 110 nm, 40 nm to 240 nm, 40 nm to 220 nm, 40 nm to 190 nm, 40 nm to 170 nm, 40 nm to 155 nm, 40 nm to 145 nm, 40 nm to 115 nm, 40 nm to 100 nm, 50 nm to 115 nm, or 50 nm to 100 nm.

[0213] In some forms, the platinum(II) complex of any one of formulas I-IV may have a τ within any of the above-mentioned ranges. em k r QY, λ maxAnd / or FWHM. In some forms, the platinum(II) complex of any one of formulas I-IV may have a τ in solution or in a membrane of up to 3.0 μs, up to 2.5 μs, up to 2.0 μs, 0.5 μs to 3.0 μs, 0.8 μs to 3.0 μs, 1.0 μs to 3.0 μs, 0.5 μs to 2.5 μs, 0.8 μs to 2.5 μs, 1.0 μs to 2.5 μs, 0.5 μs to 2.0 μs, 0.8 μs to 2.0 μs, or 1.0 μs to 2.0 μs. em ; and QY obtained in solution or in a membrane at room temperature, for example based on the emission spectrum of the platinum(II) complex as described above, at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, 50% to 90%, 55% to 90%, 60% to 90%, 50% to 80%, 55% to 80%, or 60% to 80%. In some forms, the platinum(II) complex of any one of formulas I-IV may have a τ in solution or in a membrane of up to 3.0 μs, up to 2.5 μs, up to 2.0 μs, 0.5 μs to 3.0 μs, 0.8 μs to 3.0 μs, 1.0 μs to 3.0 μs, 0.5 μs to 2.5 μs, 0.8 μs to 2.5 μs, 1.0 μs to 2.5 μs, 0.5 μs to 2.0 μs, 0.8 μs to 2.0 μs, or 1.0 μs to 2.0 μs. em At least 1.0 x 10⁻⁶ in solution or in a membrane. 5 s -1 At least 1.4x10 5 s -1 1.0x10 5 s -1 Up to 25.0x10 5 s -1 1.0x10 5 s -1 Up to 20.0x10 5 s -1 1.0x10 5 s -1 Up to 15.0x10 5 s -1 1.0x10 5 s -1 Up to 12.0x10 5 s -1 1.0x10 5 s -1 Up to 10.0x10 5 s -1 1.0x10 5 s -1 Up to 8.0x10 5 s -1 1.0x105 s -1 Up to 6.0x10 5 s -1 1.4x10 5 s -1 Up to 25.0x10 5 s -1 1.4x10 5 s -1 Up to 20.0x10 5 s -1 1.4x10 5 s -1 Up to 15.0x10 5 s -1 1.4x10 5 s -1 Up to 12.0x10 5 s -1 1.4x10 5 s -1 Up to 10.0x10 5 s -1 1.4x10 5 s -1 Up to 8.0x10 5 s -1 or 1.4x10 5 s -1 Up to 6.0x10 5 s -1 kr; in solution or in a membrane, at room temperature, at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, 50% to 90%, 55% to 90%, 60% to 90%, 50% to 80%, 55% to 80%, or 60% to 80% of QY; 600nm to 1000nm, 600nm to 760nm, 600nm to 735nm, 604nm to 733nm, 600nm to 700nm, 700nm to 1000nm, 700nm to 760nm, or 704nm to 760nm of λ max; and, for example, FWHMs obtained based on the emission spectra of platinum(II) complexes as described above, up to 270 nm, up to 250 nm, up to 220 nm, up to 200 nm, up to 180 nm, up to 160 nm, up to 145 nm, up to 135 nm, up to 120 nm, up to 110 nm, up to 100 nm, up to 90 nm, up to 80 nm, 50 nm to 270 nm, 50 nm to 250 nm, 50 nm to 220 nm, 50 nm to 200 nm, 50 nm to 180 nm, 50 nm to 160 nm, 50 nm to 145 nm, 50 nm to 110 nm, 60 nm to 270 nm, 60 nm to 250 nm, 60 nm to 220 nm, 60 nm to 200 nm, 60 nm to 145 nm, 70 nm to 200 nm, or 70 nm to 145 nm.

[0214] Suitable for measuring τ of Pt(II) complexes em k r QY, λ max Exemplary solutions of and / or FWHM include those containing organic solvents. Exemplary organic solvents suitable for forming the measurement solution include, but are not limited to, methylcyclopropane, dichloromethane, and toluene, and combinations thereof. Optionally, the τ for measuring Pt(II) complexes... em k r QY, λ max The solution of and / or FWHM is degassed with an inert gas such as nitrogen, argon, or helium, or a combination thereof. This is used to measure the τ of Pt(II) complexes. em k r QY, λ max Suitable films for FWHM include films with a thickness of 10 nm to 5 μm (including endpoints) or 10 nm to 200 nm (including endpoints). The films may also contain organic compounds as host materials. Exemplary organic compounds that can be used as host materials in the films include, but are not limited to, 1,3-bis(N-carbazolyl)benzene (mCP), 3,3′-bis(9H-carbazol-9-yl)-1,1′-biphenyl (mCBP), poly(methyl methacrylate) (PMMA), polystyrene (PS), 2,8-bis(diphenylphospho)dibenzo[b,d]furan (PPF), and bis[2-(diphenylphospho)phenyl]ether oxide (DPEPO).

[0215] B. Devices containing platinum(II) complexes

[0216] Organic light-emitting components, such as light-emitting diodes (OLEDs), containing one or more Pt(II) complexes are described. Other examples suitable for organic light-emitting devices containing the Pt(II) complexes disclosed herein include, but are not limited to, light-emitting electrochemical cells (LEECs). Devices including one or more OLEDs containing one or more Pt(II) complexes include, but are not limited to, fixed visual display devices, mobile visual display devices, and lighting devices, such as smartphones, televisions, monitors, digital cameras, tablets, and lighting equipment, wearable devices, and medical monitoring devices that typically operate at room temperature.

[0217] In some forms, Pt(II) complexes may be incorporated into the emissive layer. In some forms, the emissive layer may be incorporated into an organic light-emitting device, such as an OLED. An organic light-emitting device may include one or more emissive layers, wherein each emissive layer may contain one or more of the disclosed Pt(II) complexes. In some forms, the emissive layer, or when the organic light-emitting device includes two or more emissive layers, further comprises one or more host materials, as described above. Typically, in the emissive layer or in each of the two or more emissive layers, the total concentration of the one or more host materials is greater than the total concentration of the one or more Pt(II) complexes. The term "total concentration of the one or more Pt(II) complexes" refers to the total weight of the one or more Pt(II) complexes relative to the total weight of all materials used in an emissive layer of an organic light-emitting device, such as an OLED. The term "total concentration of the one or more host materials" refers to the total weight of the one or more host materials relative to the total weight of all materials used in an emissive layer of an organic light-emitting device, such as an OLED.

[0218] Organic light-emitting devices may contain suitable amounts of Pt(II) complexes in the light-emitting layer or in each of the two or more light-emitting layers. For example, the total concentration of the one or more Pt(II) complexes in the light-emitting layer or in each of the two or more light-emitting layers may be at most 50 wt%, at most 40 wt%, at most 30 wt%, at most 20 wt%, at least 1 wt%, about 1 wt% to about 50 wt%, about 1 wt% to about 40 wt%, about 1 wt% to about 30 wt%, about 1 wt% to about 20 wt%, about 2 wt% to about 50 wt%, about 2 wt% to about 40 wt%, etc. About 2% by weight to about 30% by weight, about 2% by weight to about 20% by weight, about 4% by weight to about 50% by weight, about 4% by weight to about 40% by weight, about 4% by weight to about 30% by weight, about 4% by weight to about 20% by weight, about 1% by weight to about 16% by weight, about 2% by weight to about 16% by weight, about 4% by weight to about 16% by weight, such as about 4% by weight, about 6% by weight, about 8% by weight, about 10% by weight, about 12% by weight, or about 16% by weight.

[0219] In some forms, organic light-emitting devices, such as OLEDs, may further include an anode, a cathode, a hole transport region, and an electron transport region. The hole transport region may include a hole injection layer and / or a hole transport layer, and optionally an electron blocking layer. The electron transport region may include an electron transport layer and / or an electron injection layer, and optionally a hole blocking layer. The light-emitting layer may be located between the anode and the cathode. The hole transport region may be located between the anode and the light-emitting layer. The electron transport region may be located between the cathode and the light-emitting layer. The specific components and their arrangement within the hole transport region and electron transport region depend on the specific application.

[0220] An exemplary OLED display containing a Pt(II) complex Figure 13 In the middle. For example Figure 13As shown, the exemplary OLED 100 includes multiple layers, from bottom to top: a substrate 101, an anode 102, a hole injection layer 103, a hole transport layer 104, an optional electron blocking layer 105, a light-emitting layer 106, an optional hole blocking layer 107, an electron transport layer 108, an electron injection layer 109, and a cathode 110. The light-emitting layer 106 is formed from one or more Pt(II) complexes disclosed herein. Suitable materials for forming the anode, hole injection layer, hole transport layer, optional electron blocking layer, optional hole blocking layer, electron transport layer, electron injection layer, and cathode are known in the art, see, for example, those described in Hong et al., Adv. Mater. 2021, 2005630; Lee et al., InfoMat. 2021, 3, 61-81; and Jou et al., J. Mater. Chem. C, 2015, 3, 2974-3002. The dimensions of the individual layers in an OLED, such as the shape, length, width, and / or thickness of each layer, can vary depending on the specific application of the OLED. More specific exemplary OLEDs are described in the following embodiments.

[0221] These organic light-emitting devices can emit in the red to deep red light region with high efficiency and extended lifetime. Unbound from any theory, the shortened emission lifetime of the Pt(II) complexes disclosed herein can reduce efficiency roll-off and extend the lifetime of phosphorescent OLEDs. The stability gained from the dinuclear nature of these Pt(II) complexes can extend the lifetime of red-emitting Pt-based OLEDs.

[0222] OLEDs containing the disclosed Pt(II) complex can achieve performance at 1000 cd / m². -2 Current efficiency (“CE”) at 1000 cd m -2 Power efficiency ("PE") at 1000 cd m -2 External quantum efficiency (“EQE”) at 1000 cd m -2 LT95 evaluation under [condition]. Used for measurement at 1000 cd / m². -2 Techniques for measuring current efficiency, power efficiency, external quantum efficiency, and / or LT95 are known. For example, the EQE, CE, and PE of electroluminescent devices can be obtained using a Keithley 2400 source meter and an absolute external quantum efficiency measurement system (C9920-12, Hamamatsu Photonics), where all devices can be encapsulated in a 200 nm thick Al2O3 film deposited by atomic layer deposition (ALD) in the Kurt J. Lesker SPECTROS ALD system prior to measurement.

[0223] In some forms, OLEDs containing the disclosed Pt(II) complex may have at least 18 cd Å. -1 At least 20 cd / A, at least 25 cd / A, at least 30 cd / A, 18 cd / A to 60 cd / A, 20 cd / A to 60 cd / A, 25 cd / A to 60 cd / A, 30 cd / A to 60 cd / A, 18 cd / A to 50 cd / A, 20 cd / A to 50 cd / A, 25 cd / A to 50 cd / A, 30 cd / A to 50 cd / A, 18 cd / A to 40 cd / A, 20 cd / A to 40 cd / A, 25 cd / A to 40 cd / A, or 30 cd / A to 40 cd / A at 1000 cd m -2 Current efficiency (“CE”) at the specified level.

[0224] In some forms, OLEDs containing the disclosed Pt(II) complex may have a capacity of at least 6 lm / W, at least 10 lm / W, at least 15 lm / W, at least 20 lm / W, at least 25 lm / W, 6 lm / W to 60 lm / W, 10 lm / W to 60 lm / W, 15 lm / W to 60 lm / W, 20 lm / W to 60 lm / W, 6 lm / W to 50 lm / W, 10 lm / W to 50 lm / W, 15 lm / W to 50 lm / W, 20 lm / W to 50 lm / W, and so on. lm / W, 6lm / W to 40lm / W, 10lm / W to 40lm / W, 15lm / W to 40lm / W, 20lm / W to 40lm / W, 6lm / W to 35lm / W, 10lm / W to 35lm / W, 15lm / W to 35lm / W, 20lm / W to 35lm / W, 6lm / W to 30lm / W, 10lm / W to 30lm / W, 15lm / W to 30lm / W, or 20lm / W to 30lm / W at 1000cd / m 2 The power efficiency ("PE") at that level.

[0225] In some forms, for OLEDs containing a single emitting layer of platinum(II) complex, there is a λ having a wavelength of approximately 600 nm to approximately 700 nm. max The disclosed Pt(II) complex OLEDs may have at least 10%, at least 11%, at least 12%, at least 13%, at least 14%, at least 15%, 10% to 40%, 10% to 20%, 10% to 20%, 11% to 40%, 11% to 30%, 11% to 20%, 12% to 20%, 12% to 40%, 12% to 30%, 13% to 20%, 13% to 40%, 13% to 30%, 14% to 20%, 14% to 40%, 14% to 30%, 15% to 40%, 15% to 30%, or 15% to 20% at 1000 cd m-2 The external quantum efficiency (“EQE”) is below this level. In some forms, for OLEDs with three emitting layers containing a platinum(II) complex, a λ of approximately 600 nm to approximately 700 nm is achieved. max The disclosed Pt(II) complex OLEDs may have at least 20%, at least 30%, 20% to 60%, 20% to 50%, 20% to 40%, 25% to 60%, 25% to 50%, 25% to 40%, 30% to 60%, 30% to 50%, 30% to 40%, 35% to 60%, 35% to 50%, 35% to 40%, 40% to 60%, 40% to 50%, or 40% to 40% at 1000 cd m -2 The external quantum efficiency (“EQE”) is below this threshold. In some forms, it contains a λ value ranging from 700 nm to approximately 1000 nm. max The disclosed Pt(II) complexes in NIR OLEDs may have at least 2.5%, at least 4%, at least 5%, at least 6%, 2.5% to 20%, 4% to 20%, 5% to 20%, or 6% to 20% at 100 mA cm⁻¹ -2 External quantum efficiency (“EQE”) under the specified conditions.

[0226] In some forms, it contains a λ having a wavelength of approximately 600 nm to approximately 700 nm. max The disclosed Pt(II) complex OLEDs may have a lifespan of at least 9000h, at least 9300h, or at least 9500h, such as at least 9000h, at least 9300h, or at least 9500h at 1000cd / m². 2 The LT95 below. In some forms, it contains a λ having a wavelength from 700 nm to approximately 1000 nm. max The disclosed Pt(II) complex NIR OLEDs may have a lifespan of at least 1000h, at least 1200h, at least 1500h, at least 2000h, at least 2500h, at least 3000h, at least 3500h, at least 4000h, at least 4500h, at least 5000h, at least 5500h, at least 6000h, at least 6500h, at least 7000h, at least 7500h, at least 8000h, at least 8500h, 9000h, at least 9300h, or at least 9500h, such as at least 1000h, at least 1200h, at least 1500h, or at least 2000h at 1000cd / m². 2 The LT95 is below.

[0227] In some forms, OLEDs containing the disclosed Pt(II) complex may have a density within any of the foregoing ranges of 1000 cd / m². -2Current efficiency, power efficiency, external quantum efficiency, and / or LT95. In some forms, it contains a λ of approximately 600 nm to approximately 700 nm. max The disclosed Pt(II) complex OLEDs can have at least 18 cd A -1 At least 20 cd / A, at least 25 cd / A, at least 30 cd / A, 18 cd / A to 60 cd / A, 20 cd / A to 60 cd / A, 25 cd / A to 60 cd / A, 30 cd / A to 60 cd / A, 18 cd / A to 50 cd / A, 20 cd / A to 50 cd / A, 25 cd / A to 50 cd / A, 30 cd / A to 50 cd / A, 18 cd / A to 40 cd / A, 20 cd / A to 40 cd / A, 25 cd / A to 40 cd / A, or 30 cd / A to 40 cd / A at 1000 cd m -2 The following concentrations are permitted: CE; and at least 10%, at least 11%, at least 12%, at least 13%, at least 14%, at least 15%, 10% to 40%, 10% to 20%, 10% to 20%, 11% to 40%, 11% to 30%, 11% to 20%, 12% to 20%, 12% to 40%, 12% to 30%, 13% to 20%, 13% to 40%, 13% to 30%, 14% to 20%, 14% to 40%, 14% to 30%, 15% to 40%, 15% to 30%, or 15% to 20% in 1000 cd m -2 The EQE below (for a single luminescent layer of platinum(II) complex).

[0228] In some forms, it contains λ having a wavelength of 700 nm to approximately 1000 nm. max The disclosed Pt(II) complex NIR OLED can have at least 18 cd A -1 At least 20 cd / A, at least 25 cd / A, at least 30 cd / A, 18 cd / A to 60 cd / A, 20 cd / A to 60 cd / A, 25 cd / A to 60 cd / A, 30 cd / A to 60 cd / A, 18 cd / A to 50 cd / A, 20 cd / A to 50 cd / A, 25 cd / A to 50 cd / A, 30 cd / A to 50 cd / A, 18 cd / A to 40 cd / A, 20 cd / A to 40 cd / A, 25 cd / A to 40 cd / A, or 30 cd / A to 40 cd / A at 1000 cd m -2 CE; and at least 2.5%, at least 4%, at least 5%, at least 6%, 2.5% to 20%, 4% to 20%, 5% to 20%, or 6% to 20% at 100mA cm -2 The EQE below.

[0229] In some forms, it contains a λ having a wavelength of approximately 600 nm to approximately 700 nm. max The disclosed Pt(II) complex OLEDs can have at least 18 cd A -1 At least 20 cd / A, at least 25 cd / A, at least 30 cd / A, 18 cd / A to 60 cd / A, 20 cd / A to 60 cd / A, 25 cd / A to 60 cd / A, 30 cd / A to 60 cd / A, 18 cd / A to 50 cd / A, 20 cd / A to 50 cd / A, 25 cd / A to 50 cd / A, 30 cd / A to 50 cd / A, 18 cd / A to 40 cd / A, 20 cd / A to 40 cd / A, 25 cd / A to 40 cd / A, or 30 cd / A to 40 cd / A at 1000 cd m -2 CE values ​​below: at least 6 lm / W, at least 10 lm / W, at least 15 lm / W, at least 20 lm / W, at least 25 lm / W, 6 lm / W to 60 lm / W, 10 lm / W to 60 lm / W, 15 lm / W to 60 lm / W, 20 lm / W to 60 lm / W, 6 lm / W to 50 lm / W, 10 lm / W to 50 lm / W, 15 lm / W to 50 lm / W, 20 lm / W to 50 lm / W, 6 lm / W to 4 0 lm / W, 10 lm / W to 40 lm / W, 15 lm / W to 40 lm / W, 20 lm / W to 40 lm / W, 6 lm / W to 35 lm / W, 10 lm / W to 35 lm / W, 15 lm / W to 35 lm / W, 20 lm / W to 35 lm / W, 6 lm / W to 30 lm / W, 10 lm / W to 30 lm / W, 15 lm / W to 30 lm / W, or 20 lm / W to 30 lm / W at 1000 cd m -2 PE at the following concentrations: at least 10%, at least 11%, at least 12%, at least 13%, at least 14%, at least 15%, 10% to 40%, 10% to 20%, 10% to 20%, 11% to 40%, 11% to 30%, 11% to 20%, 12% to 20%, 12% to 40%, 12% to 30%, 13% to 20%, 13% to 40%, 13% to 30%, 14% to 20%, 14% to 40%, 14% to 30%, 15% to 40%, 15% to 30%, or 15% to 20% at 1000 cd m -2 EQE (for a single luminescent layer of a platinum(II) complex); and at least 9000 h, at least 9300 h, or at least 9500 h at 1000 cd m -2 The LT95 is below.

[0230] In some forms, it contains λ having a wavelength of 700 nm to approximately 1000 nm.max The disclosed Pt(II) complex NIR OLED can have at least 18 cd A -1 At least 20 cd / A, at least 25 cd / A, at least 30 cd / A, 18 cd / A to 60 cd / A, 20 cd / A to 60 cd / A, 25 cd / A to 60 cd / A, 30 cd / A to 60 cd / A, 18 cd / A to 50 cd / A, 20 cd / A to 50 cd / A, 25 cd / A to 50 cd / A, 30 cd / A to 50 cd / A, 18 cd / A to 40 cd / A, 20 cd / A to 40 cd / A, 25 cd / A to 40 cd / A, or 30 cd / A to 40 cd / A at 1000 cd m -2 CE values ​​below: at least 6 lm / W, at least 10 lm / W, at least 15 lm / W, at least 20 lm / W, at least 25 lm / W, 6 lm / W to 60 lm / W, 10 lm / W to 60 lm / W, 15 lm / W to 60 lm / W, 20 lm / W to 60 lm / W, 6 lm / W to 50 lm / W, 10 lm / W to 50 lm / W, 15 lm / W to 50 lm / W, 20 lm / W to 50 lm / W, 6 lm / W to 4 0 lm / W, 10 lm / W to 40 lm / W, 15 lm / W to 40 lm / W, 20 lm / W to 40 lm / W, 6 lm / W to 35 lm / W, 10 lm / W to 35 lm / W, 15 lm / W to 35 lm / W, 20 lm / W to 35 lm / W, 6 lm / W to 30 lm / W, 10 lm / W to 30 lm / W, 15 lm / W to 30 lm / W, or 20 lm / W to 30 lm / W at 1000 cd m -2 The following PE concentrations are specified: at least 2.5%, at least 4%, at least 5%, at least 6%, 2.5% to 20%, 4% to 20%, 5% to 20%, or 6% to 20% at 100 mA cm⁻¹. -2 EQE below; and at least 1000h, at least 1200h, at least 1500h, at least 2000h, at least 2500h, or at least 3000h at 1000cd / m 2 The LT95 is below.

[0231] In some forms, it contains a λ having a wavelength of approximately 600 nm to approximately 700 nm. max And OLEDs of the disclosed Pt(II) complex at concentrations of about 4 wt% to about 16 wt% or about 6 wt% to about 16 wt%, such as about 4 wt% or about 8 wt%, can have a 1000 cd m² value within any of the above ranges. -2The current efficiency, power efficiency, external quantum efficiency, and / or LT95 at the specified values. In some forms, OLEDs containing the disclosed Pt(II) complex at concentrations of about 4 wt% to about 16 wt% or about 6 wt% to about 16 wt%, such as about 4 wt% or about 8 wt%, may have a current efficiency of at least 24 cd / A, 24 cd / A to 60 cd / A, 24 cd / A to 50 cd / A, 30 cd / A to 60 cd / A, 30 cd / A to 50 cd / A, 24 cd / A to 40 cd / A, or 30 cd / A to 40 cd / A at 1000 cd m. -2 The current efficiency is at least 10%, at least 11%, at least 12%, at least 13%, at least 14%, at least 15%, 10% to 40%, 10% to 20%, 10% to 20%, 11% to 40%, 11% to 30%, 11% to 20%, 12% to 20%, 12% to 40%, 12% to 30%, 13% to 20%, 13% to 40%, 13% to 30%, 14% to 20%, 14% to 40%, 14% to 30%, 15% to 40%, 15% to 30%, or 15% to 20% at 1000 cd m -2 The external quantum efficiency (for a single luminescent layer of a platinum(II) complex) is below.

[0232] In some forms, it contains λ having a wavelength of 700 nm to approximately 1000 nm. max NIR OLEDs of the disclosed Pt(II) complex at concentrations of approximately 4 wt% to approximately 16 wt% or approximately 6 wt% to approximately 16 wt%, such as approximately 4 wt% or approximately 8 wt%, may have at least 24 cd / A, 24 cd / A to 60 cd / A, 24 cd / A to 50 cd / A, 30 cd / A to 60 cd / A, 30 cd / A to 50 cd / A, 24 cd / A to 40 cd / A, or 30 cd / A to 40 cd / A at 1000 cd m -2 Current efficiency at 100 mA cm⁻¹; and at least 2.5%, at least 4%, at least 5%, at least 6%, 2.5% to 20%, 4% to 20%, 5% to 20%, or 6% to 20%. -2 External quantum efficiency.

[0233] In some forms, it contains a λ having a wavelength of approximately 600 nm to approximately 700 nm. maxOLEDs of the disclosed Pt(II) complex at concentrations of approximately 4% to approximately 16% by weight or approximately 6% to approximately 16% by weight, such as approximately 4% by weight or approximately 8% by weight, may have at least 24 cd / A, 24 cd / A to 60 cd / A, 24 cd / A to 50 cd / A, 30 cd / A to 60 cd / A, 30 cd / A to 50 cd / A, 24 cd / A to 40 cd / A, or 30 cd / A to 40 cd / A at 1000 cd m -2 Current efficiency at 1000 cd / m²: at least 10 lm / W, at least 15 lm / W, at least 20 lm / W, at least 25 lm / W, 10 lm / W to 60 lm / W, 15 lm / W to 60 lm / W, 20 lm / W to 60 lm / W, 10 lm / W to 50 lm / W, 15 lm / W to 50 lm / W, 20 lm / W to 50 lm / W, 10 lm / W to 40 lm / W, 15 lm / W to 40 lm / W, 20 lm / W to 40 lm / W, 6 lm / W to 35 lm / W, 10 lm / W to 35 lm / W, 15 lm / W to 35 lm / W, or 20 lm / W to 35 lm / W. -2 Power efficiency at 1000 cd / m²: at least 10%, at least 11%, at least 12%, at least 13%, at least 14%, at least 15%, 10% to 40%, 10% to 20%, 10% to 20%, 11% to 40%, 11% to 30%, 11% to 20%, 12% to 20%, 12% to 40%, 12% to 30%, 13% to 20%, 13% to 40%, 13% to 30%, 14% to 20%, 14% to 40%, 14% to 30%, 15% to 40%, 15% to 30%, or 15% to 20%. -2 The external quantum efficiency (for a single emitting layer of a platinum(II) complex) is below 9000 h or at least 9300 h at 1000 cdm. -2 The LT95 is below.

[0234] In some forms, it contains λ having a wavelength of 700 nm to approximately 1000 nm. max NIR OLEDs of the disclosed Pt(II) complex at concentrations of approximately 4 wt% to approximately 16 wt% or approximately 6 wt% to approximately 16 wt%, such as approximately 4 wt% or approximately 8 wt%, may have at least 24 cd / A, 24 cd / A to 60 cd / A, 24 cd / A to 50 cd / A, 30 cd / A to 60 cd / A, 30 cd / A to 50 cd / A, 24 cd / A to 40 cd / A, or 30 cd / A to 40 cd / A at 1000 cd m -2Current efficiency at 1000 cd / m²: at least 10 lm / W, at least 15 lm / W, at least 20 lm / W, at least 25 lm / W, 10 lm / W to 60 lm / W, 15 lm / W to 60 lm / W, 20 lm / W to 60 lm / W, 10 lm / W to 50 lm / W, 15 lm / W to 50 lm / W, 20 lm / W to 50 lm / W, 10 lm / W to 40 lm / W, 15 lm / W to 40 lm / W, 20 lm / W to 40 lm / W, 6 lm / W to 35 lm / W, 10 lm / W to 35 lm / W, 15 lm / W to 35 lm / W, or 20 lm / W to 35 lm / W. -2 Power efficiency at 100 mA cm⁻¹: at least 2.5%, at least 4%, at least 5%, at least 6%, 2.5% to 20%, 4% to 20%, 5% to 20%, or 6% to 20%. -2 External quantum efficiency below; and at least 1000h or at least 1500h at 1000cd m -2 The LT95 is below.

[0235] More specific examples of current efficiency, power efficiency, external quantum efficiency, and LT95 lifetime are described in the embodiments.

[0236] III. Methods for preparing platinum(II) complexes

[0237] A.Pt(II) complex

[0238] The Pt(II) complexes and ligands forming the Pt(II) complexes described herein can be synthesized using methods known in the field of organic chemical synthesis. The target Pt(II) complex can be synthesized by reacting a bidentate and / or tetradentate ligand with a platinum precursor in a suitable solvent. Exemplary solvents include organic solvents such as dimethylformamide. The reaction solution containing the bidentate and / or tetradentate ligand and the platinum precursor can be refluxed for a suitable time to form the target Pt(II) complex. More specific reagents, reaction conditions, and the Pt(II) complexes formed are described in the examples.

[0239] B. Organic light-emitting devices

[0240] Methods for manufacturing organic light-emitting devices, such as OLEDs, containing one or more Pt(II) complexes disclosed herein are also described. An exemplary method for manufacturing OLEDs involves vacuum deposition or solution processing techniques, such as spin coating and inkjet printing. A specific exemplary method for manufacturing OLEDs containing Pt(II) complexes disclosed herein is disclosed in the embodiments.

[0241] IV. Methods using platinum(II) complexes

[0242] The Pt(II) complexes described herein can emit red and / or deep red light at room temperature with high quantum yields (e.g., >50%) and short emission lifetimes (e.g., <3 μs). Therefore, the Pt(II) complexes described herein can be incorporated into organic light-emitting devices to emit red and / or deep red light with high efficiency and extended operating lifetimes (as described above).

[0243] For example, the Pt(II) complexes described herein can be incorporated into OLEDs, light-emitting electrochemical cells (LEECs), fixed visual display devices, mobile visual display devices, or lighting devices. Examples of devices or apparatuses suitable for use as red / deep red light emitting devices incorporating the Pt(II) complexes disclosed herein include commercial applications such as smartphones, televisions, monitors, digital cameras, tablets, and lighting equipment that typically operates at room temperature.

[0244] The following paragraphs provide further insight into the disclosed compounds, methods of use, and methods of manufacture.

[0245] Paragraph 1. A platinum(II) complex having the following structure:

[0246]

[0247] in:

[0248] (a) The compound has an overall neutral charge, negative charge, or positive charge;

[0249] (b) CY1, CY2, CY3 and CY4 are independently substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, or substituted or unsubstituted cycloalkynyl.

[0250] (c) R1, R2, R3 and R4 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro or thiol; preferably, R5, R6, R7 and R8 are independently substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl; preferably, R5, R6, R7 and R8 are independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; preferably, R5, R6, R7 and R8 are independently substituted or unsubstituted aryl.

[0251] (d) n1, n2, n3, and n4 are independent integers from 0 to 10;

[0252] (e) L1 and L3 are independently single, double, triple, absent, oxygen, sulfur, amino, amide, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, carbonyl, sulfonyl, sulfonic acid, phosphoryl or phosphonyl.

[0253] (f) R5, R6, R7 and R8 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, alkoxy or aryloxy.

[0254] (g) L2 and L4 are independently single, double, triple, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, amino, amide or carbonyl; preferably, L2 and L4 are substituted or unsubstituted alkenyl.

[0255] (h)------is absent, single bond, double bond, triple bond, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, alkoxy, aryloxy, ether, polyether, sulfonyl, or thioether; and

[0256] (i) The substituent is independently a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclic, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyhexaaryl, a substituted or unsubstituted aralkyl, a substituted or unsubstituted carbonyl, a substituted or unsubstituted alkoxy, halogen, hydroxyl, phenoxy, aryloxy, alkylthio, phenylthio, arylthio, cyano, isocyano, nitro, carboxyl, amino, amide, oxo, silyl, sulfinyl, sulfonyl, sulfonic acid, phosphonium, phosphonyl, phosphoryl, phosphonyl or thiol or a combination thereof.

[0257] Paragraph 2. The platinum(II) complex of paragraph 1, wherein the complex has the following structure:

[0258]

[0259] Paragraph 3. Platinum(II) complexes of paragraphs 1 or 2, which have an overall neutral charge.

[0260] Paragraph 4. A platinum(II) complex of any one of paragraphs 1-3, wherein CY1, CY2, CY3 and CY4 are independently substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, or substituted or unsubstituted heterocyclic.

[0261] Paragraph 5. Platinum(II) complexes of any one of paragraphs 1-4, having the following structure:

[0262]

[0263] in:

[0264] (a) CY2 and CY3 are independently substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, or substituted or unsubstituted cycloalkynyl.

[0265] (b) R2 and R3 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, oxo, amino, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro or thiol;

[0266] (c) n2, n3, n5, and n6 are independent integers from 0 to 10;

[0267] (d) R5, R6, R7, and R8 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, alkoxy, or aryloxy; preferably, R5, R6, R7, and R8 are independently substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted polyaryl; preferably, R5, R6, R7, and R8 are independently substituted or unsubstituted aryl or substituted heteroaryl; preferably, R5, R6, R7, and R8 are independently substituted or unsubstituted aryl.

[0268] (e)R9 and R 10 Independently, it is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro or thiol;

[0269] (f)R 11 -R 14 and R 21 -R 24 Independently, it is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol, and optionally, R 11 and R 12 Together, R 12 and R 13 Together, R 13 and R 14 Together, R 21 and R 22 Together, R 22 and R 23 Together and / or R 23 and R 24 Together they form substituted or unsubstituted aryl groups, substituted or unsubstituted polyaryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted polyheteroaryl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted cycloalkenyl groups, substituted or unsubstituted cycloalkynyl groups, or substituted or unsubstituted heterocyclic groups.

[0270] (g) G1' and G2' are independently C or N;

[0271] (h)------is absent, single bond, double bond, triple bond, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, alkoxy, aryloxy, ether, polyether, sulfonyl, or thioether;

[0272] (i) The substituent is independently a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclic, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyhexaaryl, a substituted or unsubstituted aralkyl, a substituted or unsubstituted carbonyl, a substituted or unsubstituted alkoxy, halogen, hydroxyl, phenoxy, aryloxy, alkylthio, phenylthio, arylthio, cyano, isocyano, nitro, carboxyl, amino, amide, oxo, silyl, sulfinyl, sulfonyl, sulfonic acid, phosphonium, phosphonyl, phosphoryl, phosphonyl or thiol or a combination thereof.

[0273] Paragraph 6. A platinum(II) complex of any one of paragraphs 1-5, wherein CY2 and CY3 are independently substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl, or substituted or unsubstituted heterocyclic, and / or wherein n2 and n3 are independently integers from 2 to 4, and two adjacent R2 and / or two adjacent R3 form a substituted or unsubstituted aryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted heterocyclic, a substituted or unsubstituted cycloalkyl, a substituted or unsubstituted cycloalkenyl, or a substituted or unsubstituted cycloynyl.

[0274] Paragraph 7. Platinum(II) complexes of any one of paragraphs 1-6, having the following structure:

[0275]

[0276] in:

[0277] (a) R5, R6, R7 and R8 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, alkoxy or aryloxy; preferably, R5, R6, R7 and R8 are independently substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl; preferably, R5, R6, R7 and R8 are independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; preferably, R5, R6, R7 and R8 are independently substituted or unsubstituted aryl.

[0278] (b) R9 and R 10 Independently, it is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro or thiol;

[0279] (c)R 11 -R 14 and R 21 -R 24 Independently, it is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol, and optionally, R11 and R 12 Together, R 12 and R 13 Together, R 13 and R 14 Together, R 21 and R 22 Together, R 22 and R 23 Together and / or R 23 and R 24 Together they form substituted or unsubstituted aryl groups, substituted or unsubstituted polyaryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted polyheteroaryl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted cycloalkenyl groups, substituted or unsubstituted cycloalkynyl groups, or substituted or unsubstituted heterocyclic groups.

[0280] (d) Each ------ can be independent of being absent, bond (single, double or triple), substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, alkoxy, aryloxy, ether, polyether, sulfonyl or thioether;

[0281] (e) X1', X2', Y1'-Y8' can be independently O, S, CR 15 or NR 18 R 15 and R 18 It can independently be absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol; and

[0282] (f) The substituent is independently a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclic, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyhexaaryl, a substituted or unsubstituted aralkyl, a substituted or unsubstituted carbonyl, a substituted or unsubstituted alkoxy, halogen, hydroxyl, phenoxy, aryloxy, alkylthio, phenylthio, arylthio, cyano, isocyano, nitro, carboxyl, amino, amide, oxo, silyl, sulfinyl, sulfonyl, sulfonic acid, phosphonium, phosphonyl, phosphoryl, phosphonyl or thiol or a combination thereof.

[0283] Paragraph 8. Platinum(II) complexes of any one of paragraphs 1-7, having the following structure:

[0284]

[0285] in:

[0286] (a) R5, R6, R7 and R8 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, alkoxy or aryloxy; preferably, R5, R6, R7 and R8 are independently substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl; preferably, R5, R6, R7 and R8 are independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; preferably, R5, R6, R7 and R8 are independently substituted or unsubstituted aryl.

[0287] (b) R9 and R 10 Independently, it is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro or thiol;

[0288] (c)R 11 -R 14 R 16 R 17 and R 19 -R 24 Independently, it is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol, and optionally, R 11 and R 12 Together, R 12 and R 13 Together, R 13 and R 14 Together, R 16 and R 17 Together, R 19 and R 20 Together, R 21 and R 22 Together, R 22 and R 23 Together and / or R 23 and R24 Together they form substituted or unsubstituted aryl groups, substituted or unsubstituted polyaryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted polyheteroaryl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted cycloalkenyl groups, substituted or unsubstituted cycloalkynyl groups, or substituted or unsubstituted heterocyclic groups.

[0289] (d)------ is absent, single bond, double bond, triple bond, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, alkoxy, aryloxy, ether, polyether, sulfonyl or thioether;

[0290] (e) X1', X2', Y1', Y2', Y3', and Y4' are independently O, S, and CR. 15 or NR 18 R 15 and R 18 Independently, it can be absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol; and

[0291] (f) The substituent is independently a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclic, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyhexaaryl, a substituted or unsubstituted aralkyl, a substituted or unsubstituted carbonyl, a substituted or unsubstituted alkoxy, halogen, hydroxyl, phenoxy, aryloxy, alkylthio, phenylthio, arylthio, cyano, isocyano, nitro, carboxyl, amino, amide, oxo, silyl, sulfinyl, sulfonyl, sulfonic acid, phosphonium, phosphonyl, phosphoryl, phosphonyl or thiol or a combination thereof.

[0292] Paragraph 9. Platinum(II) complexes of paragraph 8, wherein X1', X2', Y1', Y2', Y3' and Y4' are independently CR 15 or NR 18 R 15 and R 18 It is independently absent, hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

[0293] Paragraph 10. Platinum(II) complexes of paragraphs 8 or 9, wherein X1', X2', Y1' and / or Y3' and Y2' and / or Y4' are independently NR.18 R 18 Each occurrence of is either absent, hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

[0294] Paragraph 11. Platinum(II) complexes of any one of paragraphs 8-10, wherein R 16 R 17 R 19 and R 20 It is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, or hydroxyl.

[0295] Paragraph 12. Platinum(II) complexes of any one of paragraphs 1-7, having the following structure:

[0296]

[0297] in:

[0298] (a) R5, R6, R7 and R8 are independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, alkoxy or aryloxy; preferably, R5, R6, R7 and R8 are independently substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyaryl; preferably, R5, R6, R7 and R8 are independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl; preferably, R5, R6, R7 and R8 are independently substituted or unsubstituted aryl.

[0299] (b) R9 and R 10 Independently, it is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol; preferably, R9 and R 10 Independently hydrogen, or substituted or unsubstituted alkyl; preferably, R9 and R 10 Independently hydrogen;

[0300] (c)R 11 -R 14 R 21 -R 24 and R 27 -R 34Independently, it is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, oxo, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol, and optionally, R 11 and R 12 Together, R 12 and R 13 Together, R 13 and R 14 Together, R 21 and R 22 Together, R 22 and R 23 Together, R 23 and R 24 R 27 and R 28 Together, R 28 and R 29 Together, R 29 and R 30 Together, R 31 and R 32 Together, R 32 and R 33 Together and / or R 33 and R 34 Together they form substituted or unsubstituted aryl groups, substituted or unsubstituted polyaryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted polyheteroaryl groups, substituted or unsubstituted cycloalkyl groups, substituted or unsubstituted cycloalkenyl groups, substituted or unsubstituted cycloalkynyl groups, or substituted or unsubstituted heterocyclic groups.

[0301] (d)------ is absent, single bond, double bond, triple bond, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, alkoxy, aryloxy, ether, polyether, sulfonyl or thioether;

[0302] (e) X3' and X4' are independently CR 25 or NR 26 R 25 and R 26 Independently, it can be absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro, or thiol; and

[0303] (f) The substituent is independently a substituted or unsubstituted alkyl, a substituted or unsubstituted alkenyl, a substituted or unsubstituted alkynyl, a substituted or unsubstituted heterocyclic, a substituted or unsubstituted aryl, a substituted or unsubstituted heteroaryl, a substituted or unsubstituted polyaryl, a substituted or unsubstituted polyhexaaryl, a substituted or unsubstituted aralkyl, a substituted or unsubstituted carbonyl, a substituted or unsubstituted alkoxy, halogen, hydroxyl, phenoxy, aryloxy, alkylthio, phenylthio, arylthio, cyano, isocyano, nitro, carboxyl, amino, amide, oxo, silyl, sulfinyl, sulfonyl, sulfonic acid, phosphonium, phosphonyl, phosphoryl, phosphonyl or thiol or a combination thereof.

[0304] Paragraph 13. Platinum(II) complexes of paragraph 12, wherein X3' and X4' are independently CR 25 or NR 26 R 25 and R 26 Independently, it is absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl.

[0305] Paragraph 14. Platinum(II) complexes of paragraphs 12 or 13, wherein X3' and X4' are independently NR 26 R 26 Each occurrence of is independently of absence, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl.

[0306] Paragraph 15. Platinum(II) complexes of any one of paragraphs 12-14, wherein R 27 -R 34 Independently, it is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, or hydroxyl;

[0307] Paragraph 16. Platinum(II) complexes of any one of paragraphs 12-15, wherein R 27 -R 34 It is independently hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

[0308] Paragraph 17. Platinum(II) complexes of any one of paragraphs 5-16, wherein R9 and R 10 It is independently hydrogen or a substituted or unsubstituted alkyl group.

[0309] Paragraph 18. Platinum(II) complexes of any one of paragraphs 5-17, wherein R 11 -R 14 and R 21 -R 24It is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, hydroxyl, alkoxy or aryloxy.

[0310] Paragraph 19. Platinum(II) complexes of any one of paragraphs 5-18, wherein R 11 R 12 R 21 R 22 It is hydrogen, or R 11 and R 12 Together they form substituted or unsubstituted heteroaryl groups, substituted or unsubstituted polyheteroaryl groups, or substituted or unsubstituted heterocyclic groups, and / or R 21 and R 22 Together they form substituted or unsubstituted heteroaryl groups, substituted or unsubstituted polyaryl groups, or substituted or unsubstituted heterocyclic groups.

[0311] Paragraph 20. Platinum(II) complexes of any one of paragraphs 5-19, wherein R 11 R 12 R 21 R 22 It is hydrogen, or R 11 and R 12 Together form and / or R 21 and R 22 Together

[0312]

[0313] in:

[0314] (a) Z' is O, S, CR 39 or NR 40 R 39 and R 40 Independently, it may be absent, hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro or thiol;

[0315] (b) J1' and J2' are independent of each other. R 41 and R 42Independently, J1' and J2' are hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro or thiol, and optionally, J1' and J2' together form substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, or substituted or unsubstituted cycloalkynyl.

[0316] (c) n7 is an integer from 0 to 4; and

[0317] (d)R 35 -R 38 Independently, it is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, substituted or unsubstituted heterocyclic, halogen, hydroxyl, amino, azide, alkoxy, aryloxy, cyano, isocyano, carbonyl, nitro or thiol.

[0318] Paragraph 21. Platinum(II) complexes of paragraph 20, wherein n7 and n8 are 0, and z' is O, S, or NR. 40 R 40 Each occurrence of is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocyclic, or hydroxyl.

[0319] Paragraph 22. Platinum(II) complexes of paragraphs 20 or 21, wherein R 35 -R 38 It is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, or substituted or unsubstituted heterocyclic, hydroxyl, alkoxy or aryloxy.

[0320] Paragraph 23. Platinum(II) complexes of any one of paragraphs 1-22, wherein the relationships between R5 and R8, R6 and R7, R5 and R7, and / or R6 and R8 are absent, or wherein... and / or It has a structure:

[0321]

[0322] in:

[0323] (a) A' and B' are independently substituted or unsubstituted cycloalkyl, substituted or unsubstituted cycloalkenyl, substituted or unsubstituted cycloynyl, substituted or unsubstituted aryl, substituted or unsubstituted polyaryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted polyheteroaryl, or substituted or unsubstituted heterocyclic; and

[0324] (b) Each occurrence of L5 is independently an ether, polyether, alkoxy, sulfonyl, thioether, substituted or unsubstituted heterocyclic group, substituted or unsubstituted aryl group, substituted or unsubstituted alkyl group, substituted or unsubstituted alkenyl group, or substituted or unsubstituted alkynyl group.

[0325] Paragraph 24. The platinum(II) complex of paragraph 23, wherein A' and B' are independently substituted or unsubstituted aryl or substituted or unsubstituted polyaryl; and L5 has the following structure:

[0326]

[0327] in:

[0328] (a) Q1' and Q2' are independently non-existent, O, or S; and

[0329] (b) n9 is an integer from 1 to 10.

[0330] Paragraph 25. The platinum(II) complex of paragraph 1 has the following structure:

[0331]

[0332]

[0333]

[0334]

[0335]

[0336]

[0337]

[0338]

[0339] Paragraph 26. A platinum(II) complex of any one of paragraphs 1-25, having an emission lifetime (τ) of up to 3.0 μs, up to 2.5 μs, up to 2.0 μs, 0.5 μs to 3.0 μs, 0.8 μs to 3.0 μs, 1.0 μs to 3.0 μs, 0.5 μs to 2.5 μs, 0.8 μs to 2.5 μs, 1.0 μs to 2.5 μs, 0.5 μs to 2.0 μs, 0.8 μs to 2.0 μs, or 1.0 μs to 2.0 μs in solution or in a film. em ).

[0340] Paragraph 27. A platinum(II) complex of any one of paragraphs 1-26, having a concentration of at least 1.0 x 10⁻⁶ in solution or in a membrane. 5 s -1 At least 1.4x10 5 s -1 1.0x10 5 s -1 Up to 25.0x10 5 s -1 1.0x10 5 s -1 Up to 20.0x10 5 s -1 1.0x10 5 s -1 Up to 15.0x10 5 s -1 1.0x10 5 s -1 Up to 12.0x10 5 s -1 1.0x10 5 s -1 Up to 10.0x10 5 s -1 1.0x10 5 s -1 Up to 8.0x10 5 s -1 1.0x10 5 s -1 Up to 6.0x10 5 s -1 1.4x10 5 s -1 Up to 25.0x10 5 s -1 1.4x10 5 s -1 Up to 20.0x10 5 s -1 1.4x10 5 s -1 Up to 15.0x10 5 s-1 1.4x10 5 s -1 Up to 12.0x10 5 s -1 1.4x10 5 s -1 Up to 10.0x10 5 s -1 1.4x10 5 s -1 Up to 8.0x10 5 s -1 or 1.4x10 5 s -1 Up to 6.0x10 5 s -1 The radiation attenuation rate (kr).

[0341] Paragraph 28. A platinum(II) complex of any one of paragraphs 1-27, having an emission quantum yield (“QY”) of at least 50%, at least 55%, at least 60%, at least 65%, at least 70%, 50% to 90%, 55% to 90%, 60% to 90%, 50% to 80%, 55% to 80%, or 60% to 80% in solution or in a membrane at room temperature.

[0342] Paragraph 29. A platinum(II) complex of any one of paragraphs 1-28, having a maximum emission wavelength of 600 nm to 760 nm, 604 nm to 733 nm, 600 nm to 700 nm, or 700 nm to 1000 nm (“λ”). max ”).

[0343] Paragraph 30. The platinum (II) complex of any one of paragraphs 1-29, having a full width at half maximum (“FWHM”) of up to 270 nm, up to 250 nm, up to 200 nm, up to 180 nm, up to 160 nm, up to 145 nm, up to 135 nm, up to 120 nm, up to 110 nm, up to 100 nm, up to 90 nm, up to 80 nm, 50 nm to 270 nm, 50 nm to 250 nm, 50 nm to 200 nm, 50 nm to 180 nm, 50 nm to 160 nm, 50 nm to 145 nm, 50 nm to 110 nm, 60 nm to 145 nm, 60 nm to 110 nm, 70 nm to 145 nm, or 70 nm to 110 nm.

[0344] Paragraph 31. An organic light-emitting component comprising one or more light-emitting layers, wherein each of the light-emitting layers comprises one or more platinum(II) complexes according to any one of paragraphs 1 to 30.

[0345] Paragraph 32. The organic light-emitting assembly of paragraph 31, wherein the light-emitting layer or each of the two or more light-emitting layers further comprises one or more host materials, and wherein in the light-emitting layer or each of the two or more light-emitting layers, the total concentration of the one or more host materials is greater than the total concentration of the one or more complexes.

[0346] Paragraph 33. The organic light-emitting assembly of paragraph 32, wherein the total concentration of the one or more platinum(II) complexes in the light-emitting layer or each of the two or more light-emitting layers is at most 50 wt%, at most 40 wt%, at most 30 wt%, at most 20 wt%, at least 1 wt%, about 1 wt% to about 50 wt%, about 1 wt% to about 40 wt%, about 1 wt% to about 30 wt%, about 1 wt% to about 20 wt%, about 2 wt% to about 50 wt%, about 2 wt% to about 40% by weight, about 2% to about 30% by weight, about 2% to about 20% by weight, about 4% to about 50% by weight, about 4% to about 40% by weight, about 4% to about 30% by weight, about 4% to about 20% by weight, about 1% to about 16% by weight, about 2% to about 16% by weight, about 4% to about 16% by weight, such as about 4% by weight, about 6% by weight, about 8% by weight, about 10% by weight, about 12% by weight, or about 16% by weight.

[0347] Paragraph 34. An organic light-emitting device according to any one of paragraphs 31-33, further comprising an anode, a cathode, a hole transport region, and an electron transport region.

[0348] The hole transport region includes a hole injection layer and / or a hole transport layer, and optionally an electron blocking layer.

[0349] The electron transport region includes an electron transport layer and / or an electron injection layer, and optionally a hole blocking layer.

[0350] The light-emitting layer is located between the anode and the cathode.

[0351] The hole transport region is located between the anode and the light-emitting layer, and

[0352] The electron transport region is located between the cathode and the light-emitting layer.

[0353] Paragraph 35. An organic light-emitting device according to any one of paragraphs 31-34, having an energy density of at least 18 cd / A, at least 20 cd / A, at least 25 cd / A, at least 30 cd / A, 18 cd / A to 60 cd / A, 20 cd / A to 60 cd / A, 25 cd / A to 60 cd / A, 30 cd / A to 60 cd / A, 18 cd / A to 50 cd / A, 20 cd / A to 50 cd / A, 25 cd / A to 50 cd / A, 30 cd / A to 50 cd / A, 18 cd / A to 40 cd / A, 20 cd / A to 40 cd / A, 25 cd / A to 40 cd / A, or 30 cd / A to 40 cd / A at 1000 cd m -2 Current efficiency (“CE”) at the specified level.

[0354] Paragraph 36. An organic light-emitting module according to any one of paragraphs 31-35, having a light-emitting capacity of at least 6 lm / W, at least 10 lm / W, at least 15 lm / W, at least 20 lm / W, at least 25 lm / W, 6 lm / W to 60 lm / W, 10 lm / W to 60 lm / W, 15 lm / W to 60 lm / W, 20 lm / W to 60 lm / W, 6 lm / W to 50 lm / W, 10 lm / W to 50 lm / W, 15 lm / W to 50 lm / W, 20 lm / W to 50 lm / W. / W, 6lm / W to 40lm / W, 10lm / W to 40lm / W, 15lm / W to 40lm / W, 20lm / W to 40lm / W, 6lm / W to 35lm / W, 10lm / W to 35lm / W, 15lm / W to 35lm / W, 20lm / W to 35lm / W, 6lm / W to 30lm / W, 10lm / W to 30lm / W, 15lm / W to 30lm / W, or 20lm / W to 30lm / W at 1000cd / m 2 The power efficiency ("PE") at that level.

[0355] Paragraph 37. An organic light-emitting component according to any one of paragraphs 31-36, wherein a single layer of a platinum(II) complex has at least 10%, at least 11%, at least 12%, at least 13%, at least 14%, at least 15%, 10% to 40%, 10% to 20%, 10% to 20%, 11% to 40%, 11% to 30%, 11% to 20%, 12% to 20%, 12% to 40%, 12% to 30%, 13% to 20%, 13% to 40%, 13% to 30%, 14% to 20%, 14% to 40%, 14% to 30%, 15% to 40%, 15% to 30%, or 15% to 20% of the content of a single layer of a platinum(II) complex at 1000 cd / m². -2 External quantum efficiency (“EQE”) under the specified conditions.

[0356] Paragraph 38. An organic light-emitting device according to any one of paragraphs 31-37, wherein said one or more platinum(II) complexes have a λ of 600 nm to 700 nm. max The organic light-emitting component has a light emission time of at least 9000h, at least 9300h, or at least 9500h at 1000cd / m³. 2 LT95 below, or said one or more platinum(II) complexes having a λ of 700 nm to 1000 nm. max The organic light-emitting component has a light emission time of at least 1000h, at least 1500h, or at least 2000h at 1000cd / m³. 2 The LT95 is below.

[0357] Paragraph 39. An organic light-emitting component of any one of paragraphs 31-38, wherein the organic light-emitting component is an organic light-emitting diode (“OLED”) or a light-emitting electrochemical cell (“LEEC”).

[0358] Paragraph 40. An organic light-emitting assembly of any one of paragraphs 31-39, wherein the light-emitting layer or each of the two or more light-emitting layers is formed by vacuum evaporation deposition, spin coating, ink printing or roll-to-roll printing.

[0359] Paragraph 41. An apparatus comprising one or more organic light-emitting components according to any one of paragraphs 31-40, wherein the apparatus is a fixed visual display device, a mobile visual display device, a lighting device, a wearable device, or a medical monitoring device.

[0360] The invention can be further understood by referring to the following non-limiting embodiments. Example

[0361] Example 1. Synthesis of an exemplary platinum(II) complex

[0362] Materials and methods

[0363] Preparation of cyclic metallized ligands L1 and L2

[0364] Figure 1. Synthesis of cyclic metallized ligands

[0365]

[0366] L1 and L2 were prepared according to the methods described in the literature (Pinter et al., Organometallics 2016, 35, 673-680; Pinter et al., Chem. Eur. J. 2019, 25, 14495-14499).

[0367] Preparation of bidentate and tetradentate bridging ligands L3-L6

[0368] Figure 2. Synthesis of bidentate and tetradentate bridging ligands

[0369]

[0370] L3 was prepared according to the literature method (Hirano et al., Org. Lett. 2009, 11, 1019-1022). To prepare S1 and S3, the corresponding nitrophenol (7.2 mmol), the corresponding Br(CH2)nBr (3.6 mmol), and K2CO3 (0.50 g, 3.6 mmol) were refluxed in DMF solution (20 mL) for 12 h. After the reaction, the mixture was cooled to room temperature, and ice water was poured into the reaction flask. The resulting precipitate was filtered, washed several times with water, and dried in an oven at 60 °C for 3 h to obtain the product.

[0371] To prepare S2 (n=1) or S4, the corresponding S1 or S3 (1.7 mmol), Pd / C 5% (0.028 g), and N2H4·H2O (1.72 mL) were refluxed in anhydrous ethanol (6 mL) for 12 hours. After the reaction, the mixture was cooled to room temperature and filtered through diatomaceous earth to remove Pd / C. The filtrate was evaporated and dissolved in DCM. The resulting solution was washed three times with water, then washed with brine and dried over Na2SO4. The solvent was evaporated under vacuum to obtain the product. S2 (n=2): 1,2-bis(2-aminophenoxy)ethane was obtained from BLDpharm Chemicals and used directly.

[0372] To prepare L4, 1,2-bis(2-aminophenoxy)ethane (0.1 g, 0.41 mmol) and N-phenylformimide ethyl ester (0.38 g, 2.6 mmol) were heated at 70 °C for 1 hour. The resulting viscous oil was ground with hexane until it solidified. The resulting white solid was used directly without further purification. The preparation procedure for L5 was similar to that for L4, using 1,1-bis(2-aminophenoxy)methane instead of 1,2-bis(2-aminophenoxy)ethane. The preparation procedure for L6 was similar to that for L4, using 1,6-bis(3-aminophenoxy)hexane instead of 1,2-bis(2-aminophenoxy)ethane.

[0373] Preparation of binuclear Pt(II) complexes

[0374] Figure 3. Synthesis of binuclear Pt(II) complexes

[0375]

[0376]

[0377]

[0378]

[0379] 1a: Ag₂O (76 mg, 0.32 mmol) was added to a solution of L1 (200 mg, 0.59 mmol) in anhydrous DMF (10 mL). The mixture was stirred overnight in the dark at room temperature. The solvent was then removed under vacuum, and Pt(COD)Cl₂ (221 mg, 0.59 mmol) was added to the reaction mixture. The resulting mixture was heated at 110 °C for 24 h. After cooling to room temperature, L3 (116 mg, 0.59 mmol) and potassium tert-butoxide (66 mg, 0.59 mmol) were added to the mixture, and the mixture was heated at 100 °C for 18 h. After cooling to room temperature, the reaction mixture was filtered through a short diatomaceous earth pad, and the solvent was removed under vacuum. The resulting mixture was fed into a SiO₂ column, and the product was separated as an orange solid using DCM / hexane (v / v = 1:2) as the eluent.

[0380] A mixture of 1b:[Pt(C^C)(μ-Cl)]2(C^C=1-methyl-3-phenyl-3H-imidazo[4,5-b]pyridine-1-onthium-2-ylidene) (100 mg, 0.11 mmol), L4 (96 mg, 0.22 mmol), and K2CO3 (30 mg, 0.22 mmol) was refluxed in 1,2-dichloroethane (10 mL) under argon for 12 h. After the reaction, the solvent was removed under vacuum, and the product was purified by column chromatography on SiO2 using DCM / hexane (v / v = 3:1) as the eluent.

[0381] 1b': It was separated from the same pot reaction that produced 1b. The product was purified by column chromatography on SiO2 using DCM / hexane (v / v = 3:1) as the eluent.

[0382] 1c: The synthesis method of 1c is similar to that of 1b, using L5 instead of L4. The product was purified by column chromatography on SiO2 with DCM / hexane (v / v = 3:1) as the eluent.

[0383] 1c': It was separated from the same pot reaction that produced 1c. The product was purified by column chromatography on SiO2 using DCM / hexane (v / v = 3:1) as the eluent.

[0384] The synthesis of 1d:1d is similar to that of 1b, except that L6 is used instead of L4. The product was purified by column chromatography on SiO2 using DCM / hexane (v / v = 3:1) as the eluent.

[0385] 1d': It was separated from the same pot reaction that produced 1d. The product was purified by column chromatography on SiO2 using DCM / hexane (v / v = 3:1) as the eluent.

[0386] 2a: The synthesis of 2a is similar to that of 1a, using L2 instead of L1. The compounds were separated by column chromatography using DCM / hexane (v / v = 1:1) as the eluent.

[0387] 3a: A mixture of [Pt(2-phenylpyridine)Cl]₂ (100 mg, 0.13 mmol), L₃ (59 mg, 0.3 mmol), and potassium tert-butoxide (34 mg, 0.3 mmol) was heated overnight at 80 °C in DMF solution (9 mL) under argon. After cooling to room temperature, DCM was added to the reaction mixture, and the mixture was filtered through a short diatomaceous earth pad. The solvent was then removed under vacuum, and the product was separated as a deep red solid by column chromatography on SiO₂ using DCM / hexane (v / v = 1:3) as the eluent.

[0388] 3b: The synthesis method of 3b is similar to that of 3a, using L4 instead of L3.

[0389] 4a: The synthesis method of 4a is similar to that of 3a, except that [Pt(2-(dibenzo[b,d]furan-4-yl)pyridine)Cl]2 is used instead of [Pt(2-phenylpyridine)Cl]2.

[0390] 2b: The synthesis of 2b is similar to that of 2a, using L6 instead of L3. The compounds were separated by column chromatography using DCM / hexane (v / v = 3:1) as the eluent.

[0391] 2b': It was separated from the same pot reaction that produced 2b. The product was purified by column chromatography on SiO2 using DCM / hexane (v / v = 3:1) as the eluent.

[0392] result

[0393] S1 (n=1): Light yellow solid, yield: 48%. 1 H NMR (400MHz, CDCl3) δ7.85 (dd, J=8.1, 1.6Hz, 2H), 7.63-7.56 (m, 2H), 7.51 (dd, J=8.4, 0.9Hz, 2H), 7.22-7.14 (m, 2H), 5.93 (s, 2H). 13 C NMR (101MHz, CDCl3) δ 149.63, 140.80, 134.52, 125.69, 123.14, 117.62, 91.88. HRMS (ESI-QTOF) m / z: Calculated 313.0431; Measured 313.0437 [(M + )).

[0394] S3 (n=6): Brown solid, yield: 50%. 1H NMR (400MHz, CDCl3) δ7.81 (d, J=8.0Hz, 2H), 7.72 (s, 2H), 7.42 (t, J=8.2Hz, 2H), 7 .22 (dd, J=8.2, 1.5Hz, 2H), 4.06 (t, J=6.3Hz, 4H), 1.97-1.78 (m, 4H), 1.58 (m, 4H). 13 C NMR (101MHz, CDCl3) δ 159.74, 149.35, 130.03, 121.80, 115.76, 108.78, 68.62, 29.07, 25.88. HRMS (ESI-QTOF) m / z: Calculated 361.1394; Measured 361.1405 [(M + )).

[0395] S2 (n=1): White crystalline solid, yield 0.68 g (86%). 1 H NMR (500MHz, CDC13) δ7.10 (d, J=7.9Hz, 2H), 6.88 (t, J=7.5Hz, 2H), 6.72 (t, J=8.1Hz, 4H), 5.74 (s, 2H), 3.58 (s, 6H).13C NMR (126MHz, CDCl3) δ 144.68, 137.48, 123.48, 118.69, 115.96, 115.58, 92.93. EI-MS (+ve, m / z): 230.1.

[0396] S4 (n=6): Grayish-white crystalline solid, yield: 80%. 1 H NMR (500MHz, CDCl3) δ7.04 (t, J=8.0Hz, 2H), 6.31 (dd, J=8.2, 1.5Hz, 2H), 6.26 (t, J=7.8Hz, 2H), 6.24 (d, J=2.0Hz, 2H), 3.92 (t, J=6.5Hz, 4H), 3.63 (m, 4H), 1.89-1.69 (m, 4H), 1.56-1.40 (m, 4H). 13 C NMR (101MHz, CDCl3) δ 160.38, 147.85, 130.18, 107.89, 104.72, 101.80, 67.72, 29.35, 25.99. EI-MS (+ve, m / z): 300.2.

[0397] L4: White solid, yield: 95%. 1H NMR (400MHz, CDCl3) δ8.12 (s, 2H), 7.25 (m, 5H), 7.07-6.89 (m, 13H), 4.35 (s, 4H). 13 C NMR (101MHz, CDCl3) δ155.28, 129.51, 129.31, 129.21, 124.38, 123.48, 123.46, 123. 31, 122.24, 121.55, 120.15, 119.04, 113.44, 66.96, 62.53. EI-MS (+ve, m / z): 450.2.

[0398] L5: White solid, yield: 90%. 1 H NMR (400MHz, CDCl3) δ8.14 (s, 2H), 7.27 (m, 5H), 7.15-6.92 (m, 13H), 5.73 (s, 2H). 13 C NMR (101MHz, CDCl3) δ 155.29, 129.56, 129.43, 129.39, 129.22, 124.07, 123.75, 123.62, 123.56, 121.56, 119.83, 62.54. HRMS (ESI-QTOF) m / z: Calculated value 437.1972; Measured value 437.1976 [(M + )).

[0399] L6: Grayish-white solid, yield: 88%. 1 H NMR (400MHz, CDCl3) δ8.22 (s, 2H), 7.28 (dd, J=14.6, 6.4Hz, 4H), 7.18 (t, J=9.4Hz, 3H), 7.09-6. 99 (m, 7H), 6.61 (dd, J=17.0, 8.4Hz, 5H), 3.88 (t, J=6.2Hz, 4H), 1.76 (m, 4H), 1.58-1.45 (m, 4H). 13 C NMR (101MHz, CDCl3) δ 160.21, 130.26, 129.57, 129.51, 123.59, 123.55, 119.42, 119.09, 110.58, 109.43, 106.42, 67.43, 28.67, 25.28. HRMS (ESI-QTOF) m / z: Calculated value 507.2755; Measured value 507.2741 [(M + )).

[0400] 1a: Orange solid, yield: 35 mg (49%). 1H NMR (600MHz, DMSO) δ (ppm) 8.45 (s, 2H), 8.15 (dd, J=4.9, 1.1Hz, 2H), 7.69 (dd, J=8.1 , 1.0Hz, 2H), 7.67-7.63 (m, 2H), 7.50 (d, J=7.8Hz, 4H), 7.45 (d, J=7.8Hz, 4H), 7.24( dd, J=8.1, 4.9Hz, 2H), 7.17 (t, J=7.9Hz, 4H), 7.10 (t, J=7.9Hz, 4H), 6.91 (dt, J=18. 9, 7.4Hz, 6H), 6.43 (td, J=7.7, 1.0Hz, 2H), 6.24 (td, J=7.4, 1.0Hz, 2H), 3.22 (s, 6H). 13 C NMR (151MHz, DMSO) δ 167.80, 160.17, 152.08, 150.73, 146.08, 143.65, 143.31, 133.83, 130.84, 128.47, 128.19, 127.21, 123.40, 123.26, 122.99, 122.62, 122.55, 121.16, 118.75, 117.94, 112.63, 31.77. HRMS (ESI-QTOF) m / z: Calculated value 1197.2959; Measured value 1197.2980 [(M + )).

[0401] 1b: Orange solid, yield: 11%. 1 H NMR (500MHz, CD2Cl2) δ8.86 (s, 2H), 8.21 (d, J=7.5Hz, 2H), 8.14 (t, J=3.1Hz, 2H), 7.72 (d, J=7.4Hz, 2H), 7.46 (d, J=7.8Hz, 2H), 7.28 (d, J=7.9Hz, 4H), 7.11 (d, J=3.1Hz, 4H), 7.00-6 0.87 (m, 10H), 6.81 (dd, J = 18.1, 8.9 Hz, 4H), 6.75 (t, J = 7.2 Hz, 2H), 4.33 (d, J = 7.2 Hz, 2H), 3.72 (d, J = 7.3 Hz, 2H), 2.73 (s, 6H). HRMS (ESI-QTOF) m / z: Calculated value 1255.3014; Measured value 1255.3027 [(M + )).

[0402] 1b': Orange solid, yield: 1.8%. 1H NMR (500MHz, CD2Cl2) δ8.73 (s, 2H), 8.28 (ddd, J=9.4, 6.4, 1.3Hz, 4H), 7.64 (d, J=6. 9Hz, 2H), 7.38 (dd, J=8.0, 1.1Hz, 2H), 7.21 (d, J=7.8Hz, 4H), 7.13 (dd, J=8.0, 4.9Hz, 2H), 7.05-6.88(m, 8H), 6.88-6.76(m, 4H), 6.69(d, J=6.5Hz, 2H), 6.08(t, J=7.0Hz, 2 H), 5.98 (t, J=7.4Hz, 2H), 4.32 (d, J=7.3Hz, 2H), 4.03 (s, 6H), 3.69 (d, J=7.2Hz, 2H). 13 C NMR (126MHz, CD₂Cl₂) δ 168.73, 165.25, 153.59, 152.11, 146.69, 144.77, 143.79, 142.80, 134.08, 130.65, 128.62, 128.46, 128.27, 123.72, 123.53, 123.05, 122.29, 121.91, 120.88, 117.76, 117.65, 115.66, 113.29, 70.13, 32.91. HRMS (ESI-QTOF) m / z: Calculated value 1255.3014; Measured value 1255.3008 [(M + )).

[0403] 1c: Orange solid, yield: 15 mg (11%). 1 ¹H NMR (400MHz, CD₂Cl₂) δ 8.87 (s, 2H), 8.32 (d, J = 6.8Hz, 2H), 7.94–7.80 (m, 4H), 7.61 (d, J = 6.4Hz, 2H), 7.44 (d, J = 7.7Hz, 4H), 7.16–6.88 (m, 18H), 6.84 (t, J = 7.2Hz, 2H), 5.53 (s, 2H), 2.26 (s, 6H). HRMS (ESI-QTOF) m / z: Calculated value 1240.2779; Measured value 1240.2769 [(M + )).

[0404] 1c': Orange solid, yield: 1.4%. 1H NMR (500MHz, CD2Cl2) δ8.74 (s, 1H), 8.68 (s, 1H), 8.41-8.29 (m, 2H), 7.77 (d, J=6.5Hz, 1H), 7.71 (d, J=6.7Hz, 1H), 7.64 -7.53 (m, 4H), 7.50 (d, J=6.9Hz, 1H), 7.44 (d, J=7.7Hz, 2H), 7.28 (ddd, J=12.8, 8.0, 1.3Hz, 3H), 7.14 (ddd, J=12.5, 6.3 , 3.9Hz, 4H), 7.07 (t, J=7.9Hz, 2H), 6.93-6.83 (m, 4H), 6.64 (ddt, J=23.0, 14.0, 7.1Hz, 5H), 6.54 (dd, J=7.3, 6.2Hz, 1H ), 6.36 (t, J=7.1Hz, 1H), 6.30 (t, J=7.1Hz, 1H), 5.90 (d, J=7.1Hz, 1H), 5.76 (d, J=7.0Hz, 1H), 3.89 (s, 3H), 3.66 (s, 3H). 13 C NMR (126MHz, CD2Cl2) δ169.19, 168.49, 164.49, 164.37, 153.34, 152.68, 151.42, 151.35, 147.16, 146.88, 145.15, 145 .04, 144.83, 144.65, 144.17, 143.99, 136.55, 135.34, 131.71, 130.94, 128.96, 128.69, 128.41, 128.25, 127.71, 124. 20, 123.74, 123.64, 123.61, 123.56, 123.36, 123.34, 123.19, 122.76, 122.75, 122.65, 122.44, 120.31, 119.49, 117.99, 117.88, 117.85, 112.89, 112.68, 98.97, 77.99, 33.85, 33.25. HRMS (ESI-QTOF) m / z: Calculated value 1240.2779; Measured value 1240.2736 [(M + )).

[0405] 1d: Orange solid, yield: 2%. 1H NMR (500MHz, CD2Cl2) δ8.59 (s, 2H), 7.92-7.83 (m, 4H), 7.75-7.70 (m, 2H), 7.54 (dd, J=11. 9, 4.4Hz, 6H), 7.18 (t, J=8.0Hz, 2H), 7.14-7.03 (m, 10H), 6.96 (td, J=7.4, 1.2Hz, 2H), 6.9 0 (t, J=7.3Hz, 2H), 6.56 (dd, J=10.8, 2.0Hz, 4H), 4.24-4.06 (m, 2H), 3.82 (td, J=9.2, 5.1H z, 2H), 2.26 (s, 6H), 1.83 (m, 2H), 1.69 (ddd, J=19.7, 10.9, 6.4Hz, 4H), 1.60-1.54 (m, 2H). 13 C NMR (126MHz, CD₂Cl₂) δ 169.68, 161.23, 160.28, 153.16, 152.32, 147.47, 144.33, 144.19, 135.33, 132.40, 129.33, 128.58, 126.87, 124.91, 123.57, 123.31, 122.86, 119.32, 118.05, 117.98, 114.02, 109.29, 108.35, 67.90, 31.00, 28.53, 25.29. HRMS (ESI-QTOF) m / z: Calculated value 1310.3562; Measured value 1310.3583 [(M + )).

[0406] 1d': Orange solid, yield: 10%. 1 H NMR (500MHz, CD2Cl2) δ8.59 (s, 1H), 8.54 (s, 1H), 8.03 (t, J=4.5Hz, 2H), 7.78 (m, 4H), 7.57-7.42 (m, 4H), 7.35-7.03 (m, 12H), 6.99 (t, J = 7.3Hz, 1H), 6.90 (t, J = 7.2Hz, 1H), 6.82 (t, J = 7.3Hz, 2H) , 6.71-6.51 (m, 5H), 6.48 (d, J=6.4Hz, 1H), 4.05-3.94 (m, 2H), 3.84 (dd, J=10.3, 6.5Hz, 1H), 3.7 5 (dd, J=9.1, 5.3Hz, 1H), 2.77 (s, 3H), 2.72 (s, 3H), 1.65 (dd, J=19.2, 15.3Hz, 6H), 1.43 (s, 2H). 13C NMR (126MHz, CD2Cl2) δ169.60, 161.21, 161.11, 159.91, 159.84, 154.48, 152.96, 152.83, 151.37, 147.39, 147.24, 144. 40, 144.39, 144.20, 144.18, 135.03, 135.02, 131.83, 129.56, 129.49, 128.82, 128.67, 127.37, 127.36, 124.29, 123.72 , 123.41, 122.97, 122.72, 122.69, 117.99, 117.97, 117.94, 117.91, 114.17, 113.91, 113.84, 113.72, 113.37, 113.24, 107.86, 107.63, 67.48, 66.86, 31.67, 31.63, 27.91, 24.88, 24.73.HRMS(ESI-QTOF) m / z: Calculated value 1311.3640; Measured value 1311.3682 [(M + )).

[0407] 2a: Dark red solid, yield: 20%. 1 H NMR (500MHz, CD2Cl2) δ (ppm) 8.37-8.25 (m, 2H), 8.24-8.18 (m, 2H), 7.91 (d, J=7. 1Hz, 2H), 7.64 (d, J=7.1Hz, 6H), 7.57-7.44 (m, 6H), 7.29 (dd, J=15.6, 7.5Hz, 6H) , 7.13 (t, J=7.8Hz, 4H), 7.05 (t, J=7.8Hz, 4H), 6.93 (t, J=7.3Hz, 3H), 6.84 (t, J= 7.2Hz, 3H), 6.73 (d, J=6.9Hz, 2H), 6.38 (t, J=7.4Hz, 2H), 5.87 (t, J=6.9Hz, 2H). 13 C NMR (126MHz, CD2Cl2) δ (ppm) 171.95, 159.19, 150.53, 149.72, 146.39, 141.99, 139.11, 138.22, 137.77, 135.58, 135.15, 131.88, 129.40, 128.05, 128.00, 124.25, 123.49, 122.77, 122.71, 122.65, 121.99, 114.21. HRMS (ESI-QTOF) m / z: Calculated value 1323.3177; Measured value 1323.3227 [(M + )).

[0408] 3a: Dark red solid, yield: 42 mg (30%). 1 HNMR (500MHz, CD2Cl2) δ (ppm) 8.38 (s, 2H), 7.60 (d, J = 7.8Hz, 4H), 7.55 (d, J = 5.4Hz, 2H), 7.48 (d, J = 7.8Hz, 4H), 7.37-7.27 (m, 4H), 7. 25 (t, J=7.8Hz, 4H), 7.06 (dt, J=17.0, 7.5Hz, 8H), 6.95 (dd, J=13.2, 7.0Hz, 4H), 6.87 (dd, J=13.0, 6.9Hz, 4H), 6.06 (t, J=6.2Hz, 2H). 13 C NMR (101MHz, DMSO) δ (ppm) 165.98, 159.35, 151.12, 150.50, 149.90, 144.76, 144.53, 137.10, 132.27, 128.83, 128.42, 128.33, 123.86, 123.23, 123.15, 122.37, 121.75, 120.64, 117.70. HRMS (ESI-QTOF) m / z: Calculated value 1089.0129; Measured value 1089.2523 [(M + )).

[0409] 3b: Dark red solid, yield: 10%. 1 H NMR (500MHz, CD2Cl2) δ (ppm) 8.86 (d, J = 5.3Hz, 1H), 8.51 (s, 1H), 8.02 (d, J = 7 .9Hz, 1H), 7.43 (t, J=7.6Hz, 1H), 7.28 (d, J=7.8Hz, 2H), 7.03 (d, J=8.0Hz, 1H ), 7.01-6.88 (m, 7H), 6.88-6.78 (m, 2H), 6.58 (t, J=7.4Hz, 1H), 6.39 (d, J=7. 4Hz, 1H), 6.28 (t, J=7.3Hz, 1H), 4.30 (d, J=7.3Hz, 1H), 3.68 (d, J=7.1Hz, 1H).

[0410] 4a: Dark red solid, yield: 25%. 1H NMR (500MHz, CD2Cl2) δ (ppm) 8.44 (s, 2H), 8.01 (d, J = 7.8Hz, 2H), 7.92 (d, J = 7.4Hz, 2H), 7.72-7.56 (m, 8H), 7.54-7.39 ( m, 10H), 7.36 (t, 2H), 7.30 (t, J=7.6Hz, 4H), 7.09 (q, J=7.8Hz, 6H), 6.91 (dt, J=23.4, 7.3Hz, 4H), 5.58 (t, J=6.4Hz, 2H). 13 C NMR (126MHz, CDCl3) δ (ppm) 164.61, 160.44, 155.00, 152.80, 151.52, 150.75, 150.66, 145.85, 135.77, 129.27, 128.86, 128.61, 128.17, 127.91, 125.91, 124.76, 124.59, 123.95, 123.06, 122.99, 122.88, 121.61, 120.90, 120.23, 119.80, 111.39. HRMS (ESI-QTOF) m / z: Calculated value 1269.1723; Measured value 1268.2657 [(M + )).

[0411] 2b: Dark red solid, yield: 0.5%. 1 H NMR (500MHz, CD2Cl2) δ (ppm) 8.30 (s, 2H), 8.22 (s, 2H), 7.91 (d, J = 7.4Hz, 2H), 7.81 (d, J =7.9Hz, 2H), 7.64 (m, 6H), 7.48 (d, J = 8.0Hz, 8H), 7.34 (s, 2H), 7.14 (t, J = 7.5Hz, 4H), 7.0 4(t, J=7.8Hz, 2H), 6.95 (t, J=7.0Hz, 2H), 6.65 (d, J=7.2Hz, 2H), 6.37 (d, J=7.5Hz, 4H), 5.81 (s, 4H), 4.00 (s, 2H), 3.65 (t, J=7.8Hz, 2H), 1.71 (m, 2H), 1.61 (m, 2H), 1.44 (m, 2H). 13C NMR (126MHz, CD2Cl2) δ (ppm) 172.06, 159.71, 159.45, 151.69, 149.68, 146.34 ,141.83,139.12,138.33,137.69,135.41,135.12,131.80,129.32,128.02,1 27.98, 123.88, 122.81, 122.46, 122.12, 120.45, 114.25, 109.22, 106.60, 67.64, 29.08, 25.93. HRMS (ESI-QTOF) m / z: Calculated value: 1437.3859; Measured value: 1437.3829 [(M+H)] + ].

[0412] 2b': Dark red solid, yield: 14%. 1 H NMR (500MHz, CD2Cl2) δ (ppm) 8.31 (t, J = 2.3Hz, 2H), 8.21 (t, J = 3.0Hz, 2H), 7.94 (d, J = 7.7Hz, 1H), 7.91 (d, J = 7.7 Hz, 1H), 7.85 (s, 2H), 7.70-7.43 (m, 10H), 7.34-7.21 (m, 4H), 7.12 (t, J=7.9Hz, 3H), 7.03 (t, J=7.7Hz, 2H), 6.97- 6.66 (m, 7H), 6.51 (dd, J=8.2, 2.0Hz, 1H), 6.47-6.28 (m, 4H), 5.87 (t, J=8.2Hz, 3H), 4.22-4.12 (m, 1H), 4.09-3.9 9 (m, 1H), 3.86 (dd, J=8.3, 4.9Hz, 1H), 3.80 (d, J=9.3Hz, 1H), 1.83-1.62 (m, 5H), 1.54 (s, 2H), 1.45-1.35 (m, 1H). 13C NMR (126MHz, CD2Cl2) δ (ppm) 172.09, 159.65, 159.33, 159.22, 159.15, 152.27, 151.28, 150.46, 149.75, 146.46, 14 6.39, 142.04, 139.10, 138.22, 137.75, 135.59, 135.13, 135.09, 132.00, 131.95, 129.43, 129.38, 128.92, 128.62, 128.03, 127.96, 124.29, 123.48, 122.79, 122.68, 122.60, 122.02, 115.78, 114.49, 114.21, 112.78, 111.99, 108.32, 106.59, 67.08, 66.52, 28.26, 27.44, 24.65, 24.16. HRMS (ESI-QTOF) m / z: Calculated value: 1437.3859; Measured value: 1437.3823 [(M+H)] + ].

[0413] The structure of the synthesized Pt(II) complex is shown below:

[0414]

[0415]

[0416] The X-ray crystal structures of Pt(II) complexes 1a, 1b, 1c, 2b', 3a, and 3b and their Pt-Pt contacts are shown in [the diagrams]. Figure 1A-1D middle.

[0417] Example 2. Platinum(II) complexes exhibit high emission quantum yield and shortened emission lifetime.

[0418] Materials and methods

[0419] Emission spectra of Pt(II) complexes 1a, 1b, 1b', 1c, 1c', 1d, 1d', 2a, 3a, 3b, and 4a were measured at room temperature in poly(methyl methacrylate) (“PMMA”) and 1,3-bis(N-carbazolyl)benzene (“MCP”) films, respectively. (The emission spectra were obtained by Φ...) em / τ em Calculate the radiation attenuation rate k r τ of platinum(II) complexes emThe following were obtained: (i) emission decay intensity was monitored over time using a Quanta Ray GCR 150-10 pulsed Nd:YAG laser system (pulse output: 355 nm), and (ii) τ was determined by fitting the exponential decay of formula (1) using Origin software. em Where I0 is the initial emission intensity, I(t) is the emission intensity at time t, τ is the emission lifetime, and t is time.

[0420] I(t) = I0e -t / τ

[0421] Formula (1)

[0422] The Φ values ​​of Pt(II) complexes 1a, 1b, 1b', 1c, 1c', 1d, 1d', 2a, 3a, and 3b in solution or thin film were directly obtained by absolute measurement using a Hamamatsu C11347 Quantaururus-QY Absolute PL quantum yield spectrometer (PL stands for photoluminescence). em Value. By using Pt(tpdbp) as the standard reference (Φ) r : 0.51, λ em The relative method for measuring Pt(II) complex 4a in the NIR region (λ = 770 nm) was used. max =753 (max) The solution Φ in 903nm) em Value. Then through the equation: P em =Φ r (B r / B s )(n s / n r ) 2 (D s / D r Calculate Φ em Where r and s represent the sample and reference standard, respectively, and B = 1-10 -AL Where A is the absorbance at the excitation wavelength, L is the optical path length in cm, n is the refractive index of the solvent, and D is the integrated emission intensity.

[0423] result

[0424] Photophysical properties

[0425] Pt(II) complexes 1a, 1b, 1b', 1c, 1c', 1d, 1d', 2a, 2b, 2b', 3a, 3b, and 4b exhibit red to deep red light emission (λ) at room temperature under photoexcitation in both solution and film. max =604-733nm)(see Figure 2A-2HThe emission data for these Pt(II) complexes are summarized in Table 1 below. High emission quantum yields of up to 0.8 (i.e., 80%) and short lifetimes as low as 1.3 μs have been observed. (The data is obtained by k...) r =Φ em / τ em The calculated radiation attenuation rates are all 10. 5 s -1 The magnitude.

[0426] Table 1. Emission data of Pt(II) complexes at room temperature

[0427]

[0428] Table 1 (continued). Emission data of Pt(II) complexes at room temperature

[0429]

[0430]

[0431] Example 3. OLEDs containing platinum(II) complexes exhibit high emission quantum yield and extended lifetime.

[0432] Materials and methods

[0433] Vacuum deposition method for manufacturing OLEDs

[0434] OLEDs were formed by vacuum deposition of Pt(II) complexes in film form. Specifically, indium tin oxide (ITO) coated glass with a sheet resistance of 10 Ω / sq was used as the anode substrate. Prior to film deposition, the patterned ITO substrate was cleaned with detergent, rinsed in deionized water, acetone, and isopropanol, and then dried in an oven in a cleanroom for 1 hour. The slide was then treated in a UV-ozone chamber for 5 minutes. -7 OLEDs were fabricated using the Kurt J. Lesker SPECTROS vacuum deposition system at millibar base pressure. In the vacuum chamber, organic materials were deposited... s -1 The doping process in the EML was achieved sequentially by thermal deposition at rates of 0.02 and 0.2 nm. -1 LiF (1.2 nm) and Al (100 nm) were thermally deposited at high rates. The film thickness was determined in situ using a calibrated oscillating quartz crystal sensor.

[0435] result

[0436] The emission spectra and performance characteristics of devices containing Pt(II) complexes 1a, 1b, 1d', 2a, 4a, 1c, and 2b' are shown in [the table below]. Figures 3A-3DThe devices are 4A-4D, 5A-5D, 6A-6B, 7A-7F, 8A-8D, 9A-9D, 14A-14B, and 15A-15D. Performance data for these devices are summarized in Tables 2-8, 15, and 16, respectively. Device lifetime measurements for devices containing Pt(II) complexes 1a, 1d', 2a, 1b, 1c, and 2b' are shown in... Figure 10-12 Tables 16-18 and 17-19 summarize their lifetime measurement data, respectively. Table 12 compares the performance of devices containing Pt(II) complexes 1a and 2a with known red emitters. Table 13 summarizes the performance data of commercially available OLEDs from Merck, Sumitomo, DuPont, and UDC. Table 14 summarizes the performance data of red and deep red OLEDs reported by Universal Display.

[0437] Vacuum-deposited OLEDs based on 1a and 1b exhibited red electroluminescence with CIE coordinates near (0.63, 0.37) and (0.64, 0.36), respectively. In both cases, the maximum EL did not change significantly when the dopant concentration increased from 6 wt% to 12 wt%, and the free wave height (FWHM) remained at ~80 nm. At 1000 cd / m²... -2 At high luminous intensity levels, these devices achieved an external quantum efficiency of 18.7% in case 1a and 15.1% in case 1b. In particular, device lifetime measurements for the 1a-based devices showed high values ​​of LT90–150 hours, with an initial luminous shell density (L0) of 8000 cd / m². -2 .

[0438] Furthermore, near-infrared (“NIR”) OLEDs have been fabricated using vacuum deposition on a 2a substrate. When the electron transport layer (ETL) thickness increased from 40 nm to 120 nm, the maximum EL value shifted from 688 nm to 706 nm, while the free wave height (FWHM) remained around 100 nm. The device exhibited excellent performance at 1000 cd / m². -2 The NIR OLED exhibits a high EQE of up to 13% at its luminance level. Based on 2a, the NIR OLED also demonstrates a high LT90–380 hours, with an initial luminance (L0) of 2000 cd / m². -2 .

[0439] Table 2. Vapor deposition devices containing 1a (System I) * Performance data

[0440]

[0441] *System I device structure: ITO / HAT-CN (5nm) / TAPC (20nm) / Tris-PCz (10nm) / Tris-PCz:B4PYPPM:Pt-1a (30nm) / B4PYPPM (50nm) / Liq (1nm) / Al (100nm).

[0442] Table 3. Vapor deposition devices containing 1a (System II) * Performance data

[0443]

[0444] * System II device structure: ITO / HAT-CN (5nm) / TAPC (40nm) / TCTA (10nm) / TCTA:TPBi:Pt-1a / TPBi (10nm) / TmPyPb (40nm) / LiF (1.2nm) / Al (100nm).

[0445] Table 4. Performance data of vapor deposition devices containing 1b

[0446]

[0447] Table 5. Performance data of vapor-deposited devices containing 1d' at a doping concentration of 4% by weight.

[0448]

[0449] Table 6. Performance data of vapor deposition devices containing 6% 2a and ETL of various thicknesses

[0450]

[0451] Table 7. Performance data of vapor-deposited devices containing 2a at doping concentrations of 4%–16% by weight.

[0452]

[0453] Table 8. Performance data of vapor deposition devices containing 6% 4a and ETL of various thicknesses

[0454]

[0455] Table 9. Lifetime measurement data of OLEDs containing 1a (the luminous intensity measured at LT is called L0)

[0456] 1a concentration <![CDATA[L0(cd m -2 )]]> LT97(h) LT90(h) 8% by weight 8500 23 134 12% by weight 8100 21 152 16% by weight 8030 20 158

[0457] Table 10. Lifetime measurement data of OLEDs containing 1d' (the luminous intensity measured at LT is called L0)

[0458] 1d' concentration <![CDATA[L0(cd m -2 )]]> LT97(h) LT95(h) 4% by weight 12000 35.2 90.6

[0459] Table 11. Lifetime measurement data of OLEDs containing 2a (the luminous intensity at LT is 2000 nits, referred to as L0).

[0460] 2a concentration <![CDATA[L0(cd m -2 )]]> LT97(h) LT95(h) LT90(h) 4% by weight 2000 2.94 8.57 34.6 8% by weight 2000 19.5 54.1 202 12% by weight 2000 90.4 162 381 16% by weight 2000 83.4 153 368

[0461] Table 12. Performance of devices containing Pt(II) complexes 1a and 2a compared to known red light emitters, measured under the same conditions (same temperature, pressure, and using the same measuring instruments and parameters, etc.).

[0462]

[0463] # Forrest et al., Nanophotonics 2021; 10(1): 31-40)

[0464] b IHS Markit 2019

[0465] *Estimation at laboratory scale

[0466] The device architecture used for lifetime measurements in 1a may differ from that in Systems I and II. The value for 9300h is estimated based on results from tests conducted by industrial partners at L0 at 5000 nits (LT95–600h). The formula LT(L1) = LT(L0) × (L0 / L1) is used with n = 1.7. 1.7 The acceleration factor (where L0 refers to the initial luminous intensity and L1 refers to the desired luminous intensity) at 1000 nits is LT95 = ~600x(5000 / 1000)^1.7 = ~9255.

[0467] ~Structure of the previously tested dye:

[0468]

[0469] Table 13. Performance of commercially available OLEDs from Merck, Sumitomo, DuPont, and UDC, reported by the manufacturers and measured under identical conditions (same temperature, pressure, using the same measuring instruments and parameters, etc.).

[0470] Red light Merck Sumitomo DuPont UDC (Evaporable DC) Efficiency (cd / A) 23 24 22 29 CIE(x, y) 0.65，0.35 0.66，0.34 0.65，0.35 0.66，0.34 LT95(h) at 1000 nits 10,000 5,800 9,500 23,000

[0471] Table 14. Performance of red and deep red OLEDs reported by Universal Display (website oled-info.com / udc-pholed-material-performance-update-green-now-reaches-14-million-hours)

[0472]

[0473] Table 15. Performance data of vapor-deposited devices containing 1c at doping concentrations of 4-16 wt%.

[0474]

[0475] Table 16. Performance data of vapor-deposited devices containing 2b' at doping concentrations of 4-16 wt%.

[0476]

[0477] Table 17. Lifetime measurement data of OLEDs containing 1b (the luminous intensity measured at LT is called L0).

[0478] 1b concentration <![CDATA[L0(cd m -2 )]]> LT97(h) LT95(h) 8% by weight 5000 2.9 6.2

[0479] Table 18. Lifetime measurement data of OLEDs containing 1c (the luminous intensity at LT is referred to as L0).

[0480] 1c concentration <![CDATA[L0(cd m -2 )]]> LT97(h) LT95(h) 4% by weight 14400 4.3 17.5

[0481] Table 19. Lifetime measurement data of OLEDs containing 2b' (the luminous intensity at LT is referred to as L0).

[0482] 2b' concentration <![CDATA[L0(cd m- 2 )]]> LT97(h) LT95(h) 4% by weight 2600 54.5 125.2

Claims

1. A platinum (II) complex having a structure selected from the group consisting of:

2. An organic light-emitting assembly comprising one light-emitting layer or two or more light-emitting layers, wherein the light-emitting layer or each light-emitting layer of the two or more light-emitting layers comprises the platinum (II) complex of claim 1.

3. The organic light-emitting assembly of claim 2, wherein the light-emitting layer or each light-emitting layer of the two or more light-emitting layers further comprises one or more host materials, and wherein the total concentration of the one or more host materials is greater than the total concentration of the one or more complexes in the light-emitting layer or each light-emitting layer of the two or more light-emitting layers.

4. The organic light-emitting assembly of claim 3, wherein the total concentration of the one or more platinum (II) complexes in the light-emitting layer or each light-emitting layer of the two or more light-emitting layers is at most 50 wt.%.

5. The organic light-emitting assembly of claim 3, wherein the total concentration of the one or more platinum (II) complexes in the light-emitting layer or each light-emitting layer of the two or more light-emitting layers is at least 1 wt.%.

6. The organic light-emitting assembly of claim 3, wherein the total concentration of the one or more platinum (II) complexes in the light-emitting layer or each light-emitting layer of the two or more light-emitting layers is 1 wt.% to 50 wt.%.

7. The organic light-emitting assembly of claim 3, wherein the total concentration of the one or more platinum (II) complexes in the light-emitting layer or each light-emitting layer of the two or more light-emitting layers is 2 wt.% to 30 wt.%.

8. The organic light-emitting assembly of claim 3, wherein the total concentration of the one or more platinum (II) complexes in the light-emitting layer or each light-emitting layer of the two or more light-emitting layers is 4 wt.% to 16 wt.%.

9. The organic light-emitting assembly of claim 2, further comprising an anode, a cathode, a hole transport zone, and an electron transport zone, wherein the hole transport zone comprises a hole injection layer and / or a hole transport layer, wherein the electron transport zone comprises an electron transport layer and / or an electron injection layer, wherein the light-emitting layer is positioned between the anode and the cathode, wherein the hole transport zone is positioned between the anode and the light-emitting layer, and wherein the electron transport zone is positioned between the cathode and the light-emitting layer.

10. The organic light-emitting assembly of claim 9, wherein the hole transport zone comprises a hole injection layer and / or a hole transport layer, and optionally an electron blocking layer, wherein the electron transport zone comprises an electron transport layer and / or an electron injection layer, and optionally a hole blocking layer.

11. The organic light emitting component of claim 2, having a current efficiency ("CE") of at least 18 cd / A at 1000 cd / m 2 2.

12. The organic light-emitting device according to claim 2, having an efficiency of 18 cd / A to 60 cd / A at 1000 cd / m². 2 Current efficiency ("CE") at the specified level.

13. The organic light-emitting device according to claim 2, having a light emission power of 30 cd / A to 60 cd / A at 1000 cd / m². 2 Current efficiency ("CE") at the specified level.

14. The organic light emitting assembly of claim 2, having a power efficiency ("PE") of at least 6 lm / W at 1000 cd / m 2 2.

15. The organic light-emitting device according to claim 2, having a light emission power of 6 lm / W to 60 lm / W at 1000 cd / m². 2 Power efficiency ("PE") at the specified level.

16. The organic light-emitting device according to claim 2, having a light emission power of 20 lm / W to 30 lm / W at 1000 cd / m². 2 Power efficiency ("PE") at the specified level.

17. The organic light emitting assembly of claim 2 having an external quantum efficiency ("EQE") of at least 10% for a single layer of the platinum (II) complex at 1000 cd m -2 2.

18. The organic light-emitting device according to claim 2, wherein a single layer of the platinum(II) complex has a content of 10% to 40% at 1000 cd / m². -2 External quantum efficiency ("EQE") under the specified conditions.

19. The organic light-emitting device according to claim 2, wherein a single layer of the platinum(II) complex has a spectral density of 15% to 20% at 1000 cd / m². -2 External quantum efficiency ("EQE") under the specified conditions.

20. The organic light emitting component according to claim 2, wherein the one or more platinum (II) complexes have a λ max maxof from 600 nm to 700 nm, and the organic light emitting component has an LT95 of at least 9000 h at 1000 cd / m 2 2. The organic light emitting component according to claim 2, wherein the one or more platinum (II) complexes have a λ max maxof from 700 nm to 1000 nm, and the organic light emitting component has an LT95 of at least 1000 h at 1000 cd / m 2 2.

21. The organic light-emitting assembly of claim 2, wherein the organic light-emitting assembly is an organic light-emitting diode ("OLED") or a light-emitting electrochemical cell ("LEEC").

22. The organic light-emitting assembly of claim 2, wherein the light-emitting layer or each light-emitting layer of the two or more light-emitting layers is formed by vacuum evaporation deposition, spin coating, ink printing, or roll-to-roll printing.

23. A device comprising one or more organic light emitting assemblies of any one of claims 2-22, wherein the device is a stationary visual display apparatus, a mobile visual display apparatus, a lighting apparatus, a wearable device, or a medical monitoring apparatus.

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