Pyridocarbazole tetradentate platinum (II) complex, electronic device, apparatus and use thereof

Abstract

The present invention belongs to the technical field of the preparation of organic electroluminescent materials, and particularly relates to a pyridocarbazole tetradentate platinum (II) complex, an electronic device, an apparatus and the use thereof. The present invention provides a platinum (II) complex having a fused-ring structure. The complex has a pyridocarbazole tetradentate structure. Such a fused-ring structure is applied to the tetradentate platinum complex for the first time in the present invention. The material involved in the present invention has good chemical stability and thermal stability, making it easy to prepare an evaporated OLED device. After the complex is combined with a fluorescent doping material, the transport of holes and electrons can be balanced, making energy transfer between a host and a guest more efficient. Upon verification, an organic electroluminescent device fabricated by using the complex of the present invention as a light-emitting layer has both significantly improved current efficiency and significantly prolonged lifetime, and also has significantly reduced turn-on voltage. The photochromic purity of the device can also be improved when the complex is used in combination with a phosphorescent sensitized boron-containing compound.

Description

Pyridinecarbazole tetradentate platinum (II) complex, electronic device, apparatus and application thereof TECHNICAL FIELD

[0001] The present application belongs to the technical field of organic electroluminescent material preparation, and particularly relates to a pyridinecarbazole tetradentate platinum (II) complex, an electronic device, an apparatus and application thereof. BACKGROUND

[0002] Organic light emitting diode (OLED) is a new generation of full-color display and lighting technology. Compared with liquid crystal display, OLED has the advantages of slow response speed, small viewing angle, need for backlight source, high energy consumption and the like. As a kind of self-luminous device, OLED does not need a backlight source and is energy-saving. Moreover, OLED has low driving voltage, fast response speed, high resolution and contrast, wide viewing angle, excellent low-temperature performance, and can be made thinner and flexible. In addition, OLED has the advantages of low production cost, simple production process and large-area production. Therefore, OLED has a wide and huge application prospect in high-end electronic products and aerospace. With the gradual increase of investment, further in-depth research and development, and upgrading and transformation of production equipment, OLED has a very wide application scenario and development prospect in the future.

[0003] The core of OLED development is the design and development of light-emitting materials. In the currently applied OLED device, the light-emitting layer almost entirely uses a host-guest light-emitting system mechanism, that is, a guest light-emitting material is doped in a host material. The energy system of the host material is generally greater than that of the guest light-emitting material, so that the energy is transferred from the host material to the guest material, and the guest material is excited to emit light. Commonly used organic phosphorescent guest materials are heavy metal atoms such as iridium (III), platinum (II) and palladium (II). Commonly used phosphorescent organic materials mCBP (3,3'-bis(9-carbazolyl)-biphenyl) and 2,6-mCPy (2,6-bis(9-carbazolyl)-pyridine) have high efficiency and high triplet energy level. When they are used as organic materials, the triplet energy can be effectively transferred from the light-emitting organic material to the guest phosphorescent light-emitting material. However, due to the characteristics of mCBP that the hole is easy to transmit and the electron is difficult to flow, and the poor hole transport of 2,6-mCPy, the charge of the light-emitting layer is unbalanced, which results in the reduction of the current efficiency of the device. Compared with iridium (III) complexes, platinum (II) complex phosphorescent materials have more raw materials and lower preparation cost. However, there are still some technical difficulties in the development of platinum complex materials and devices. The problem of how to reduce the height of the shoulder peak in the emission spectrum to improve the color purity of the material molecular light emission still needs to be solved, and therefore it is urgent to develop a new type of phosphorescent platinum (II) complex. SUMMARY

[0004] In view of the above, the present application aims to provide one or more guest phosphorescent materials applied to organic electroluminescent devices. Specifically, a tetradentate metal platinum (II) complex having a pyridine and carbazole structure is provided. It has good chemical stability and thermal stability, and is easy to prepare an evaporation type OLED device. After being prepared into a device, it can improve current efficiency and lifetime, reduce turn-on voltage, prolong device lifetime, and obtain higher color purity.

[0005] In one aspect, the present application provides a metal platinum (II) complex having a structure shown in Formula I,

[0006] wherein ring A represents a C3-C30 nitrogen-containing heteroaryl group, X1, X2 are each independently selected from N, C; R 1 , R 2 , R 3 , R 4 , R 5 are each independently represented as mono-substituted, di-substituted, tri-substituted, tetra-substituted, or non-substituted; R 1 , R 2 , R 3 , R 4 , R 5 are each independently represented as any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C60 heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 arylamine, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C60 siloxane; when containing a substituent, the substituent is selected from deuterium, cyano, halogen, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C18 aryl, C5-C18 heteroaryl.

[0007] In many embodiments, R 1 is represented as any one of hydrogen, deuterium, cyano, fluorine, C1-C14 alkyl, C1-C14 fluoroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C10 oxyalkyl, substituted or unsubstituted C3-C30 siloxane; when containing a substituent, the substituent is selected from deuterium, cyano, fluorine, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, pyridyl.

[0008] In many embodiments, R 2represents any of hydrogen, deuterium, C1-C4 alkyl.

[0009] In many embodiments, R 3 represents any of hydrogen, deuterium, cyano, fluorine, C1-C14 alkyl, C1-C14 fluoroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C12 cycloamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, C3-C30 silyl, C1-C10 oxyalkyl, C1-C10 siloxanyl; when containing a substituent, said substituent is selected from the group consisting of deuterium, cyano, fluorine, methyl, ethyl, propyl, isopropyl, t-butyl, phenyl.

[0010] In many embodiments, R 4 represents any of hydrogen, deuterium, cyano, fluorine, C1-C14 alkyl, C1-C14 fluoroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C12 cycloamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, C3-C30 silyl, C1-C10 oxyalkyl, C1-C10 siloxanyl; when containing a substituent, said substituent is selected from the group consisting of deuterium, cyano, fluorine, methyl, ethyl, propyl, isopropyl, t-butyl, phenyl.

[0011] In many embodiments, R 5 represents any of hydrogen, deuterium, cyano, fluorine, C1-C14 alkyl, C1-C14 fluoroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C12 cycloamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, C3-C30 silyl, C1-C10 oxyalkyl, C1-C10 siloxanyl; when containing a substituent, said substituent is selected from the group consisting of deuterium, cyano, fluorine, methyl, ethyl, propyl, isopropyl, t-butyl, phenyl.

[0012] In many embodiments, the complex represented by formula I has one of the structures represented by formula Pt-(I), Pt-(II) or Pt-(III):

[0013] wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6represents hydrogen, deuterium, C1-C30alkyl, substituted or unsubstituted C6-C30aryl; when containing a substituent, said substituent is selected from the group consisting of deuterium, fluorine, C1-C10alkyl, C6-C18aryl.

[0014] In many embodiments, R 6 represents hydrogen, deuterium, C1-C30alkyl, substituted or unsubstituted C6-C30aryl; when containing a substituent, said substituent is selected from the group consisting of deuterium, fluorine, C1-C10alkyl, C6-C18aryl.

[0015] In another aspect, the present application also provides an organic electroluminescent device comprising a cathode, an anode, and an organic functional layer interposed therebetween; the organic functional layer comprising a metal platinum (II) complex having the structure of formula I as described above. In many embodiments, the organic functional layer comprises an emission layer comprising a metal platinum (II) complex having the structure of formula I as described above.

[0016] In many embodiments, the emission layer further comprises a fluorescent dopant material; the fluorescent dopant material is selected from any one or more of the compounds represented by formula (BN1) to formula (BN5) as described above.

[0017] wherein Y is O, S, Se, or NR 300 ;

[0018] Y 1 , Y 2 , Y 3 , Y 4 each independently represents O, S, Se, or N;

[0019] R b -R e each independently represents mono-substitution, di-substitution, tri-substitution, tetra-substitution, or no substitution; R b -R e each independently is selected from the group consisting of hydrogen, deuterium, N, C1-C30alkyl, C6-C30aryl. a , R7-R 12 each independently represents hydrogen, deuterium, N, C1-C30alkyl, C6-C30aryl, C6-C30N heteroaryl.

[0020] In another aspect, the present application also provides an organic optoelectronic device, comprising: a substrate layer; a first electrode on the substrate; an organic light-emitting functional layer on the first electrode; a second electrode on the organic light-emitting functional layer; wherein the organic light-emitting functional layer comprises a metal platinum (II) complex having the structure of formula I as described above. For example, the metal platinum (II) complex can be included in the organic light-emitting functional layer as a light-emitting material.

[0021] In many embodiments, the organic light-emitting functional layer further comprises one or more fluorescent dopant materials.

[0022] Preferably, the fluorescent dopant material is selected from any one or more of the compounds represented by formula (BN1) to formula (BN5) as described above.

[0023] In another aspect, the present application also provides a composition comprising a metal platinum (II) complex having the structure of formula I as described above.

[0024] In many embodiments, the composition further comprises a fluorescent dopant material selected from any one or more of the compounds represented by formula (BN1) to formula (BN5) as described above.

[0025] In another aspect, the present application also provides a formulation comprising a metal platinum (II) complex having the structure of formula I as described above and at least one solvent. The solvent is not particularly limited and can be an unsaturated hydrocarbon solvent, a halogenated saturated hydrocarbon solvent, a halogenated unsaturated hydrocarbon solvent, an ether solvent or an ester solvent known to those skilled in the art; wherein the unsaturated hydrocarbon solvent is toluene, xylene, mesitylene, tetralin, n-butylbenzene, sec-butylbenzene or tert-butylbenzene; the halogenated saturated hydrocarbon solvent is carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane or bromocyclohexane; the halogenated unsaturated hydrocarbon solvent is chlorobenzene, dichlorobenzene or trichlorobenzene; the ether solvent is tetrahydrofuran or tetrahydropyran; and the ester solvent is benzoic acid alkyl ester.

[0026] The present application also provides a display or lighting device, which comprises one or more of the organic optoelectronic devices as described above.

[0027] Compared with the prior art, the present application has the following advantages:

[0028] The present application provides a kind of metal platinum (II) complex of annelated structure, the complex has pyridine and carbazole tetradentate structure, the present application first applies this kind of annelated structure to tetradentate platinum complex.The material involved in the present application has good chemical stability and thermal stability, and is easy to prepare evaporation type OLED device.It can balance the transmission of holes and electrons after being combined with fluorescent doping material, so that the energy transfer between host and guest is more efficient.It has been verified that the organic electroluminescent device made of the complex of the present application as the light-emitting layer has obvious improvement in current efficiency and service life, and the starting voltage is significantly reduced.The application of phosphorescent sensitized boron-containing compound can improve the color purity of light of the device. BRIEF DESCRIPTION OF DRAWINGS

[0029] Fig. 1 is the HOMO, LUMO orbital distribution and energy level difference of part of the metal complex of the present application;

[0030] Fig. 2 is the room temperature emission spectrum diagram of platinum complex Pt1 in dichloromethane solution;

[0031] Fig. 3 is the room temperature emission spectrum diagram of platinum complex Pt2 in dichloromethane solution;

[0032] Fig. 4 is the room temperature emission spectrum diagram of platinum complex Pt3 in dichloromethane solution. DETAILED DESCRIPTION

[0033] The content of the present application is described in detail as follows. The description of the constituent elements described below is sometimes based on the representative embodiment or specific example of the present application, but the present application is not limited to such embodiment or specific example.

[0034] The term "substituted" used in the present application is intended to include all permissible substituents of organic compounds. In a broad aspect, permissible substituents include noncyclic and cyclic, branched and unbranched, carbocyclic and heterocyclic, and aromatic and nonaromatic substituents of organic compounds. Illustrative substituents include, for example, those described below. The permissible substituents of an appropriate organic compound can be one or more, and the same or different for each. For purposes of this application, heteroatoms such as nitrogen can have hydrogen substituents and / or any permissible substituents of organic compounds described herein, which satisfy the valencies of the heteroatoms. The present application is not intended to be limited in any way by the permissible substituents of organic compounds. Also, the term "substitution" or "substituted with" includes the implicit proviso that such substitution is in accordance with permitted valence of the substituted atom and the substituent, and that the substitution results in a stable compound (e.g., a compound that does not spontaneously undergo transformation (e.g., by rearrangement, cyclization, elimination, etc.)). It is also intended that, in certain aspects, the substituents can be further optionally substituted (i.e., further substituted or unsubstituted) unless specifically indicated otherwise.

[0035] In defining various terms, "R1" - "R 12 " are used as general symbols to represent various specific substituents. These symbols can be any substituent, not limited to those disclosed herein, and when they are defined in one instance as certain substituents, they can be defined in other instances as some other substituents.

[0036] As used herein, "R1", "R2", "R3"... "R n " (where n is an integer) can independently have one or more of the groups listed above. For example, if R1is a straight chain alkyl group, one of the hydrogen atoms of the alkyl group can optionally be replaced with a hydroxyl, alkoxy, alkyl, halogen, etc. Depending on the group selected, the first group can be incorporated within the second group, or alternatively, the first group can be pendant, i.e., attached to the second group. The nature of the group selected will determine whether the first group is embedded or attached to the second group.

[0037] As used herein, the term "alkyl" is a branched or unbranched saturated hydrocarbon radical of 1 to 30 carbon atoms, preferably the alkyl group is an alkyl group containing 1 to 14 carbon atoms, more preferably 1 to 10 carbon atoms. For example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, sec-butyl, t-butyl, n-pentyl, i-pentyl, sec-pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, eicosyl, tetracosyl, etc. The alkyl group can be cyclic or acyclic. The cyclic alkyl group can be cyclopropane, cyclopentane, cyclohexane, the alkyl group can be branched or unbranched. The alkyl group can also be substituted or unsubstituted. For example, the alkyl group can be substituted with one or more groups including, but not limited to, the optionally substituted alkyl, cycloalkyl, alkoxy, amino, halogen, hydroxyl, nitro, silyl, sulfo-oxo, or thiol groups described herein.

[0038] The term "aryl" as used herein is any carbon-based aromatic group containing 6 to 30 carbon atoms, preferably aryl is an aromatic group containing 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms. The carbon-based aromatic groups include, but are not limited to, phenyl, naphthyl, biphenyl, terphenyl, phenoxyphenyl, anthryl, phenanthryl, and the like. The term "aryl" also includes "heteroaryl", which is defined as a group containing an aromatic group having at least one heteroatom incorporated within the ring of the aromatic group. Examples of heteroatoms include, but are not limited to, nitrogen, oxygen, sulfur, and phosphorus. The aryl group can be substituted or unsubstituted. The aryl group can be substituted with one or more groups including, but not limited to, alkyl, cycloalkyl, alkoxy, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, heteroaryl, aldehyde, amino, carboxyl, ester, halogen, hydroxyl, carbonyl, azido, nitro, silyl, sulfo-oxo, or mercapto as described herein.

[0039] The term "amine" or "amino" as used herein is represented by the formula -NR 1 R 2 , wherein R 1 and R 2 may be independently selected from hydrogen, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, aryl, or heteroaryl.

[0040] Examples of the term "halogen" or "halo" as used herein include, but are not limited to, fluorine, chlorine, bromine, and iodine.

[0041] In one aspect, the present application provides a metal platinum (II) complex of the formula I,

[0042] wherein ring A represents a C3-C30 nitrogen heteroaryl group, X1, X2are each independently selected from N, C; R 1 , R 2 , R 3 , R 4 , R 5 are each independently represented as mono-substituted, di-substituted, tri-substituted, tetra-substituted, or non-substituted; R 1 , R 2 , R 3 , R 4 , R 5each independently represents any of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C60 heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 arylamine, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C60 siloxane group; when containing a substitution, the substitution is selected from the group consisting of deuterium, cyano, halogen, C1-C10 alkyl, C3-C10 cycloalkyl, C6-C18 aryl, C5-C18 heteroaryl.

[0043] In many embodiments, R 1 represents any of hydrogen, deuterium, cyano, fluorine, C1-C14 alkyl, C1-C14 fluoroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C10 oxyalkyl, substituted or unsubstituted C3-C30 siloxane group; when containing a substitution, the substitution is selected from the group consisting of deuterium, cyano, fluorine, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, pyridyl.

[0044] In many embodiments, R 2 -R 3 represents any of hydrogen, deuterium, cyano, fluorine, C1-C14 alkyl, C1-C14 fluoroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, C3-C30 silyl, C3-C30 arylsilyl, C1-C10 oxyalkyl, diphenylamine, substituted or unsubstituted C3-C30 siloxane group; when containing a substitution, the substitution is selected from the group consisting of deuterium, cyano, fluorine, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl.

[0045] In many embodiments, R 4 represents any of hydrogen, deuterium, cyano, fluorine, C1-C14 alkyl, C1-C14 fluoroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted C3-C30 silyl, C1-C10 oxyalkyl, C1-C10 siloxane group; when containing a substitution, the substitution is selected from the group consisting of deuterium, cyano, fluorine, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl.

[0046] In many embodiments, R 5 represents any one of hydrogen, deuterium, cyano, fluorine, C1-C14 alkyl, C1-C14 deuterated alkyl, substituted or unsubstituted C6-C30 aryl, pyridyl, substituted or unsubstituted C1-C10 oxyalkyl, substituted or unsubstituted C1-C10 siloxanyl; when containing a substituent, said substituent is selected from the group consisting of deuterium, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl.

[0047] In many embodiments, the complex of formula I has one of the structures of formula Pt-(I), Pt-(II) or Pt-(III):

[0048] wherein R 1 , R 2 , R 3 , R 4 , R 5 are the same as R 1 , R 2 , R 3 , R 4 , R 5 in formula I; R 6 represents hydrogen, deuterium, C1-C14 alkyl, substituted or unsubstituted C6-C30 aryl; when containing a substituent, said substituent is selected from the group consisting of deuterium, fluorine, C1-C10 alkyl, C6-C18 aryl.

[0049] In many embodiments, R 6 represents hydrogen, deuterium, methyl, ethyl, isopropyl, substituted or unsubstituted phenyl; when containing a substituent, said substituent is selected from the group consisting of deuterium, fluorine, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl.

[0050] In many embodiments, the Pt complex of formula I can be selected from the following structures:

[0051] Further, the present application also provides the use of the metal platinum (II) complex having the structure of formula I as above in electronic devices.

[0052] Further, the electronic device includes an organic electroluminescent device (OLED), an organic integrated circuit (O-IC), an organic field effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, an organic photoreceptor, an organic field quenching device (O-FQD), a light emitting electrochemical cell (LEC), and an organic laser diode (O-laser).

[0053] In another aspect, the present application also provides an organic electroluminescent device comprising the metal platinum (II) complex having the structure of formula I as described above.

[0054] Further, the organic electroluminescent device comprises a cathode, an anode, and an organic functional layer interposed therebetween; the organic functional layer comprises the metal platinum (II) complex having the structure of formula I as described above.

[0055] Preferably, the organic functional layer comprises an emitting layer, and the emitting layer comprises the metal platinum (II) complex having the structure of formula I as described above.

[0056] In one aspect, the present application provides a composition comprising a guest material and a host material; the guest material is selected from the metal platinum (II) complex of formula I as described above.

[0057] In many embodiments, the composition further comprises a fluorescent dopant material; the fluorescent dopant material is selected from any one or more of the compounds represented by formula (BN1) to formula (BN5):

[0058] wherein Y is O, S, Se, or NR 300 ;

[0059] Y 1 , Y 2 , Y 3 , Y 4 each independently represents O, S, Se, or N;

[0060] R b -R e each independently represents mono-substitution, di-substitution, tri-substitution, tetra-substitution, or no substitution; R b -R e each independently is selected from the group consisting of hydrogen, deuterium, N, C1-C30 alkyl, C6-C30 aryl, and the like; the R a , R7-R 12 each independently represents hydrogen, deuterium, N, C1-C30 alkyl, C6-C30 aryl, C6-C30 N heteroaryl, and the like.

[0061] Preferably, said R a , R7, R 10 are each independently selected from the group consisting of substituted or non- substituted diphenylamino, substituted or non-substituted carbazolyl; said substitution can be multiple substitution, when containing substituents, said substituents are selected from the group consisting of deuterium, C1-C30 alkyl, C6-C30 aryl.

[0062] Preferably, said R 300 , R8, R9, R 11 , R 12 are each independently selected from the group consisting of hydrogen, C1-C30 alkyl, C6-C30 aryl.

[0063] Further preferably, at least one hydrogen in formula (BN1) - formula (BN5) can be replaced by deuterium.

[0064] Further, said fluorescent dopant material is selected from any one of the chemical structures shown below, wherein Ph represents a phenyl group, D4 and D5 mean substituted by 4 and 5 deuterium atoms, respectively:

[0065] The disclosed metal platinum (II) complexes can exhibit desirable properties and have emission and / or absorption spectra that can be tuned by selection of appropriate ligands.

[0066] The complexes of the present application can be prepared using a variety of methods, including but not limited to those described in the examples provided herein.

[0067] It is to be noted that both the general description above and the detailed description below are exemplary and explanatory only and are not restrictive.

[0068] The application can be more readily understood by reference to the following detailed description and examples included therein.

[0069] Before disclosing and describing the compounds, devices, and / or methods of the present invention, it should be understood that they are not limited to specific synthetic methods (otherwise indicated) or specific reagents (otherwise indicated), as these are, of course, subject to variation. It should also be understood that the terminology used in this invention is for descriptive purposes only and is not intended to be limiting. While any methods and materials similar to or equivalent to those described in this invention may be used in this practice or experiment, exemplary methods and materials are described below. All raw materials and solvents used in the synthetic examples are commercially available unless otherwise specified, and the solvents were used directly without further processing.

[0070] The substrate described in this invention can be any substrate typically used in organic electronic devices. It can be a glass or transparent plastic substrate, or an opaque material such as silicon or stainless steel, or a flexible PI film. Different substrates have different mechanical strengths, thermal stability, transparency, surface smoothness, and water resistance, and their applications vary depending on their properties. As materials for the hole injection layer, hole transport layer, and electron injection layer, any known materials used in OLED devices can be selected, and this invention does not impose specific limitations.

[0071] Synthesis Examples

[0072] The examples of compound synthesis, composition, devices, or methods below are intended to provide a general approach to the industry and are not intended to limit the scope of this patent. While we strive for accuracy in the data (quantities, temperatures, etc.) mentioned in the patent, some errors may still exist. Unless otherwise specified, weighings are performed separately, temperatures are in °C or room temperature, and pressures are close to atmospheric pressure.

[0073] The examples below provide methods for preparing novel compounds, but the preparation of such compounds is not limited to these methods. In this field of expertise, since the compounds protected in this invention are easily modified and prepared, their preparation can be carried out using the methods listed below or other methods. The examples below are merely illustrative and are not intended to limit the scope of this patent. Temperature, catalyst, concentration, reactants, and reaction process can all be varied to select different conditions for preparing the compounds with different reactants.

[0074] 1 HNMR (500MHz), 1 HNMR (400MHz), 13 CNMR (126MHz) spectra were measured on an ANANCE III (500M) nuclear magnetic resonance spectrometer; unless otherwise specified, DMSO-d6 or CDCl3 containing 0.1% TMS was used as the solvent for all NMR measurements. 1HNMR spectra if in CDCl3as solvent, with TMS (δ = 0.00 ppm) as internal standard; in DMSO-d6as solvent, with TMS (δ = 0.00 ppm) or residual DMSO peak (δ = 2.50 ppm) or residual water peak (δ = 3.33 ppm) as internal standard. 13 CNMR spectra in CDCl3(δ = 77.00 ppm) or DMSO-d6(δ = 39.52 ppm) as internal standard. HPLC-MS Agilent 6210 TOF LC / MS type mass spectrometer was used for determination; HRMS spectra were determined on an Agilent 6210 TOF LC / MS type liquid chromatography-time of flight mass spectrometer. 1 HNMR spectra data: s = singlet, d = doublet, t = triplet, q = quartet, p = quintet, m = multiplet, br = broad.

[0075] Synthetic route

[0076] Synthetic route of intermediate PyCz-OH:

[0077] Synthesis of intermediate Py-Br-Cz: Into a 100 mL three-necked flask with magnetic stirrer was added intermediate 2-methoxycarbazole (5 g, 25.3 mmol, 1.0 eq), 2-fluoro-3-bromopyridine (4.46 g, 25.3 mmol, 1.0 eq), cesium carbonate (9.09 g, 27.9 mmol, 1.1 eq), then the mixture was pumped with nitrogen, and N,N-dimethylformamide (40 mL) was added under nitrogen protection. The mixture was stirred in an oil bath at 130 °C for 24 hours. After cooling to room temperature, the reaction mixture was quenched with water, extracted with dichloromethane and water three times, and then the organic phases were combined and dried over anhydrous sodium sulfate. After rotary evaporation and sample stirring, column chromatography was used for separation, and the eluent was petroleum ether / ethyl acetate = 50:1-20:1. Finally, intermediate Py-Br-Cz was obtained as a white solid, 8.33 g, with a yield of 93%. 1 HNMR (500 MHz, DMSO-d6) δ (ppm): 3.76 (s, 3H), 6.60 (d, J = 2.5 Hz, 1H), 6.92 (dd, J = 8.5, 2.5 Hz, 1H), 7.05 (dt, J = 8.0, 1.0 Hz, 1H), 7.26 (td, J = 7.5, 1.0 Hz, 1H), 7.29 - 7.34 (m, 1H), 7.62 (dd, J = 8.0, 4.5 Hz, 1H), 8.09 - 8.14 (m, 2H), 8.50 (dd, J = 8.5, 1.5 Hz, 1H), 8.75 (dd, J = 4.5, 1.5 Hz, 1H).

[0078] Synthesis of intermediate PyCz: Into a 100 mL three-necked flask with a magnetic bar was added intermediate Py-Br-Cz (3 g, 8.49 mmol, 1.0 eq), palladium acetate (191 mg, 0.85 mmol, 0.1 eq), potassium carbonate (5.87 g, 42.5 mmol, 5.0 eq), n-tetrabutylammonium bromide (2.73 g, 8.49 mmol, 1.0 eq), then the flask was degassed with nitrogen using an oil pump, N,N-dimethylacetamide (30 mL) was added under nitrogen, and the mixture was bubbled with nitrogen for 30 min. The mixture was stirred at 150 °C for 4 h. After cooling to room temperature, the reaction mixture was quenched with water, and the organic phase was extracted with dichloromethane three times and combined, and dried over anhydrous sodium sulfate. The mixture was rotary evaporated and chromatographed on a silica gel column using petroleum ether / ethyl acetate (100:1-50:1) as eluent to give intermediate PyCz as a light yellow solid (1.73 g, 75% yield). 1 HNMR (500 MHz, DMSO-d6) δ (ppm): 3.97 (s, 3H), 7.05 (dd, J = 8.5, 2.5 Hz, 1H), 7.46 (dd, J = 7.5, 5.0 Hz, 1H), 7.63 (t, J = 7.5 Hz, 1H), 7.70 (d, J = 2.5 Hz, 1H), 8.13 (dd, J = 7.5, 1.5 Hz, 2H), 8.17 (d, J = 8.5 Hz, 1H), 8.58 (dd, J = 5.0, 2.0 Hz, 1H), 8.66 (dd, J = 7.5, 1.5 Hz, 1H).

[0079] Synthesis of intermediate PyCz-OH: Into a 50 mL three-necked flask with a magnetic bar was added intermediate PyCz (1.01 g, 3.91 mmol, 1.0 eq), hydrobromic acid (48%) (18 mL), and the mixture was stirred at 120 °C for 19 h. After cooling to room temperature, the reaction mixture was neutralized with sodium bicarbonate solution, and the organic phase was extracted with dichloromethane three times and combined, and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the crude product was slurried with dichloromethane to give intermediate PyCz-OH as a gray-green solid (900 mg, 93% yield).

[0080] 1HNMR (500 MHz, DMSO-d6) δ (ppm): 3.97 (s, 1H), 6.88 (dd, J = 8.5, 2.5 Hz, 1H), 7.43 (dd, J = 7.5, 5.0 Hz, 1H), 7.58 - 7.62 (m, 2H), 8.06 (dd, J = 10.0, 8.5 Hz, 2H), 8.09 (d, J = 7.5 Hz, 1H), 8.56 (dd, J = 5.0, 2.0 Hz, 1H), 8.64 (dd, J = 8.0, 2.0 Hz, 1H).

[0081] Example 1: Synthesis of Pt1

[0082] The intermediate PyZo-Br was subjected to C-O coupling with PyCz-OH, followed by metallation to give the complex Pt1.

[0083] The route is as follows

[0084] Synthesis of ligand L1: Into a dry schlenk tube with magnetic stirrer, potassium phosphate (1.52 g, 7.2 mmol, 2.0 eq) was added, then the schlenk tube was dried by heating with hot air gun while pumping, then PrZo-Br (900 mg, 3.58 mmol, 1.0 eq), PyCz-OH (926 mg, 3.58 mmol, 1.0 eq), 2-picolinic acid (88 mg, 0.72 mmol, 0.2 eq), cuprous iodide (68 mg, 0.36 mmol, 0.1 eq) were added in turn, then dimethyl sulfoxide (12 mL) was added under nitrogen protection, the mixture was stirred in an oil bath at 100 °C for 19 hours, then the reaction was stopped. Cooled to room temperature, extracted with ethyl acetate, dried with anhydrous sodium sulfate. Rotary evaporation, column chromatography separation, eluent: petroleum ether / ethyl acetate = 20:1-10:1, finally ligand L1 was obtained, orange gum solid 767 mg, yield 50%. 1HNMR (500 MHz, DMSO-d6) δ (ppm): 2.13 (s, 3H), 2.33 (s, 3H), 6.05 (s, 1H), 7.20 (dd, J = 10, 3.0 Hz, 1H), 7.24 (dd, J = 11, 3.0 Hz, 1H), 7.29 (t, J = 3.0 Hz, 1H), 7.35 - 7.38 (m, 1H), 7.44 (dd, J = 10, 6.5 Hz, 1H), 7.57 (t, J = 10 Hz, 1H), 7.67 (t, J = 9.0 Hz, 1H), 7.75 (d, J = 3.0 Hz, 1H), 8.17 - 8.23 (m, 2H), 8.33 (d, J = 10.5 Hz, 1H), 8.51 - 8.53 (m, 1H), 8.65 - 8.67 (m, 1H).

[0085] Synthesis of complex Pt1: Into a 100 mL three-necked flask with magnetic stirrer and condenser, ligand L1 (920 mg, 2.14 mmol, 1.0 eq), potassium tetrachloroplatinate (936 mg, 2.25 mmol, 1.05 eq), n-tetrabutylammonium bromide (69.2 mg, 0.214 mmol, 0.1 eq) were added, then the flask was degassed with oil pump and flushed with nitrogen. Acetic acid (30 mL) was added under nitrogen protection and the mixture was bubbled with nitrogen for 30 min. The mixture was stirred at room temperature for 12 h, then stirred at 120 °C for 48 h. After cooling to room temperature, the reaction was quenched with water, extracted with dichloromethane and water for three times, then the organic phase was combined and dried over anhydrous sodium sulfate. The solvent was removed by rotary evaporation and the residue was purified by column chromatography with petroleum ether / ethyl acetate = 25:1 as eluent to give ligand Pt1 as green solid, 181 mg, yield 14%.

[0086] 1 HNMR (500 MHz, DMSO-d6) δ (ppm): 2.56 (s, 3H), 2.78 (s, 3H), 6.53 (s, 1H), 6.95 - 6.97 (m, 1H), 7.12 (d, J = 10.5 Hz, 1H), 7.25 (t, J = 10 Hz, 1H), 7.33 (d, J = 10.0 Hz, 1H), 7.50 (dd, J = 9.5, 7.0 Hz, 1H), 7.67 (t, J = 9.5 Hz, 1H), 7.86 (d, J = 10.5 Hz, 1H), 8.06 - 8.11 (m, 2H), 8.86 - 8.89 (m, 1H), 8.94 (d, J = 7.0 Hz, 1H), 11.96 (s, 2H). HRMS [M+H] + : 622.1.

[0087] Example 2: The synthesis route of Pt2 is as follows

[0088] Synthesis of complex Pt2:

[0089] Synthesis of intermediate 2-Me-NO2: Into a 25 mL three-neck flask with magnetic stirrer and condenser, add o-nitroaniline (1 g, 7.24 mmol, 1.0 eq), then add N,N-dimethylformamide (10 mL), cool to 0 °C, slowly add sodium hydride (318 mg, 7.96 mmol, 1.1 eq), keep low temperature for 10 min, then add iodomethane (1.03 g, 7.24 mmol, 1.0 eq), gradually restore to room temperature, stir the reaction for 6 hours. Quench the reaction with acetic acid, then extract with ethyl acetate, dry with anhydrous sodium sulfate. Spin dry and mix, separate by column chromatography, eluent: petroleum ether / ethyl acetate = 20:1, finally get intermediate 2-Me-NO2, orange red liquid 1.07 g, yield 97%.

[0090] 1 HNMR (500 MHz, DMSO-d6) δ (ppm): 2.95 (d, J = 5.0 Hz, 3H), 6.67 (ddd, J = 8.5, 7.0 1.5 Hz, 1H), 6.97 (dd, J = 9.0, 1.5 Hz, 1H), 7.51 - 7.57 (m, 1H), 8.05 (dd, J = 8.5, 1.5 Hz, 1H), 8.15 (s, 1H).

[0091] Synthesis of intermediate 2-Me-NH2: Into a 50 mL single-neck flask with magnetic stirrer and condenser, add 2-Me-NO2 (1.07 g, 7 mmol, 1.0 eq), 10% palladium on carbon (224 mg, 0.21 mmol, 0.03 eq), then add ethyl acetate to dissolve, pump hydrogen three times, then pass hydrogen balloon into the reaction bottle, stir the reaction at room temperature for 12 hours. Put diatomite on the sand core funnel, filter the reaction liquid and rinse several times, then spin dry and mix the filtrate, separate by column chromatography, eluent: petroleum ether / ethyl acetate = 20:1, finally get ligand 2-Me-NH2, pink liquid 750 mg, yield 87%. The product obtained in this step is not stable and is not convenient to characterize, so it is directly used in the subsequent reaction.

[0092] Synthesis of intermediate 2-Me-NH: A 50 mL three-necked flask with magnetic stirring bar and condenser was charged with 2-Me-NH2(181 mg, 1.49 mmol, 1.0 eq), PyCz-Cl (632 mg, 1.49 mmol, 1.0 eq), Pd2(dba)3(41 mg, 0.045 mmol, 0.03 eq), JohnPhos (2-(di-tert-butylphosphino)biphenyl) (27 mg, 0.09 mmol, 0.06 eq), sodium tert-butoxide (285 mg, 2.97 mmol, 2.0 eq), toluene (15 mL) was added under nitrogen protection, the mixture was stirred in an oil bath at 100 °C for 9 h, then the reaction was stopped. After cooling to room temperature, the mixture was spin-dried, column chromatography was used for separation, eluent: petroleum ether / ethyl acetate = 25:1-10:1, finally 2-Me-NH was obtained as a brown-red foamy solid, 692 mg, yield 91%. The product obtained from this step was unstable and inconvenient to characterize, so it was directly used in the subsequent reaction.

[0093] Synthesis of ligand L2: A dry schlenk tube with a magnetic stirring bar was charged with 2-Me-NH (692 mg, 1.36 mmol, 1.0 eq), ammonium hexafluorophosphate (442 mg, 2.71 mmol, 2.0 eq), oil pump was used to replace nitrogen, then triethyl orthoformate (6 mL) was added under nitrogen protection, the mixture was stirred in an oil bath at 80 °C for 8 h, then the reaction was stopped. After cooling to room temperature, the mixture was spin-dried, column chromatography was used for separation, eluent: dichloromethane / ethyl acetate = 1:1-20:1, finally ligand L2 was obtained as a foamy solid, 541 mg, yield 60%.

[0094] 1 HNMR (500 MHz, DMSO-d6) δ (ppm): 1.39 (s, 9H), 4.11 (s, 3H), 7.32 (dd, J = 10.5, 3.0 Hz, 1H), 7.40 (t, J = 2.5 Hz, 1H), 7.48 (dd, J = 11, 6.5 Hz, 1H), 7.59-7.60 (m, 1H), 7.60-7.64 (m, 1H), 7.65 (t, J = 2.0 Hz, 1H), 7.67-7.71 (m, 1H), 7.71-7.75 (m, 1H), 7.86-7.88 (m, 1H), 7.90 (d, J = 3.0 Hz, 1H), 8.08-8.10 (m, 1H), 8.21-8.26 (m, 2H), 8.38 (d, J = 10.5 Hz, 1H), 8.54 (dd, J = 6.0, 2.0 Hz, 1H), 8.70 (dd, J = 9.5, 2.0 Hz, 1H), 10.10 (s, 1H).

[0095] Synthesis of complex Pt2: To a dry Schlenk tube with magnetic bar was added ligand L2 (541 mg, 0.81 mmol, 1.0 eq), ((1,5-cyclooctadiene) dichloroplatinum) (318 mg, 0.85 mmol, 1.05 eq) and sodium acetate (199 mg, 2.43 mmol, 3.0 eq) sequentially, then the tube was pumped and purged with nitrogen, DEDM (diethyleneglycol dimethyl ether) (8 mL) was added under nitrogen, the mixture was bubbled with nitrogen for 30 min, then the mixture was stirred in the dark at 120 °C for 72 h. The reaction was cooled to room temperature, quenched with water, then extracted with dichloromethane three times, the organic phases were combined and dried over anhydrous sodium sulfate, then concentrated and chromatographed on silica gel, eluent: petroleum ether / dichloromethane = 2:1-1 :1, to give complex Pt2 as a foamy solid 310 mg, 53% yield.

[0096] 1 HNMR (500 MHz, DMSO-d6) δ (ppm): 1.46 (s, 9H), 4.19 (s, 3H), 7.00 (d, J = 1.5, Hz, 1H), 7.23 (d, J = 8.0 Hz, 1H), 7.49-7.52 (m, 1H), 7.53-7.55 (m, 1H), 7.56-7.60 (m, 1H), 7.68-7.71 (m, 2H), 7.83-7.85 (m, 1H), 7.92 (d, J = 8.5 Hz, 1H), 8.08-8.13 (m, 2H), 8.32 (d, J = 8.0 Hz, 1H), 8.94-8.95 (m, 1H), 9.27-9.29 (m, 1H). HRMS [M+H] + : 714.2.

[0097] Example 3: Synthesis of Pt3

[0098] Synthesis route of complex Pt3 is as follows:

[0099] Synthesis of intermediate t-Bu-Bpin-Br: Into a 100 mL three-necked flask with a magnetic bar was added 1,3-dibromo-5-tert-butyl-benzene (3 g, 10.27 mmol, 1.0 eq), then the flask was flushed with nitrogen using oil pump, then tetrahydrofuran (50 mL) was added under nitrogen atmosphere, then the flask was gradually cooled to -78 °C, then 2.5 M n-butyllithium (4.3 mL, 10.78 mmol, 1.05 eq) was added dropwise at low temperature, then the reaction was continued for 1 h at low temperature, then isopropyl alcohol pinacolboronate (2.3 g, 12.33 mmol, 1.2 eq) was added dropwise at low temperature, then the reaction was continued for 17 h by gradually warming to room temperature. The reaction mixture was quenched with saturated aqueous ammonium chloride solution, then extracted with ethyl acetate, then dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, then the crude product was obtained as 3.4 g, which was used as such in the subsequent reaction as it could not be purified by column chromatography.

[0100] Synthesis of intermediate t-Bu-Py-Br: Into a 50 mL three-necked flask with a magnetic bar was added intermediate t-Bu-Bpin-Br (3.4 g, 10 mmol, 1.5 eq), potassium carbonate (1.84 g, 13.3 mmol, 2.0 eq), tetrakis(triphenylphosphine)palladium (154 mg, 0.13 mmol, 0.02 eq), then the flask was flushed with nitrogen using oil pump, then 1,4-dioxane: water (16 mL: 4 mL) was added under nitrogen atmosphere, then 2-bromopyridine (1.05 g, 6.6 mmol, 1.0 eq) was added, then the mixture was bubbled with nitrogen for 30 min. The reaction was continued for 19 h by stirring the mixture in 90 °C oil bath, then the reaction mixture was cooled to room temperature, then quenched with water, then extracted with ethyl acetate, then dried over anhydrous sodium sulfate. The mixture was evaporated, then column chromatography was performed using petroleum ether / ethyl acetate (50:1) as eluent, then intermediate t-Bu-Py-Br was obtained as a colorless transparent liquid 1.76 g in 91% yield.

[0101] 1 HNMR (400 MHz, CDC13) δ (ppm): 1.40 (s, 9H), 7.26-7.30 (m, 1H), 7.59 (t, J = 2.0 Hz, 1H), 7.70-7.75 (m, 1H), 7.76-7.82 (m, 1H), 7.96 (dt, J = 7.2, 1.6 Hz, 2H), 8.72 (ddd, J = 4.4, 2.0, 1.2 Hz, 1H).

[0102] Synthesis of Ligand L3: Into a 50 mL three-necked flask with magnetic stirring bar and dried, potassium phosphate (2.57 g, 12 mmol, 2.0 eq) was added, followed by a hot air gun to remove water vapor from a schlenk tube while pumping, then t-Bu-Py-Br (1.76 g, 6.06 mmol, 1.0 eq), PyCz-OH (1.57 g, 6.06 mmol, 1.0 eq), 2-picolinic acid (149 mg, 1.2 mmol, 0.2 eq), cuprous iodide (115 mg, 0.6 mmol, 0.1 eq) were added in turn, and then the mixture was pumped with nitrogen, dimethyl sulfoxide (15 mL) was added under nitrogen protection, the mixture was stirred in an oil bath at 100 °C for 10 h, and then the reaction was stopped. After cooling to room temperature, it was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The sample was spin-dried and column chromatography was used for separation, eluent: petroleum ether / ethyl acetate = 50:1-20:1, finally the ligand L3 was obtained as a foamy gel-like solid 1.47 g, yield 52%. 1 HNMR (500 MHz, DMSO-d6) δ (ppm): 1.37 (s, 9H), 7.21 (dd, J = 8.5, 2.5 Hz, 1H), 7.30-7.35 (m, 2H), 7.42 (dd, J = 7.5, 5.0 Hz, 1H), 7.64-7.68 (m, 2H), 7.74 (d, J = 2.5 Hz, 1H), 7.84 (td, J = 8.0, 2.0 Hz, 1H), 7.95-7.98 (m, 1H), 7.99-8.02 (m, 1H), 8.16 (d, J = 7.5 Hz, 1H), 8.20 (d, J = 7.5 Hz, 1H), 8.30 (d, J = 8.5 Hz, 1H), 8.48 (dd, J = 5.0, 2.0 Hz, 1H), 8.58-8.61 (m, 1H), 8.64 (dd, J = 7.5, 1.5 Hz, 1H).

[0103] Synthesis of Complex Pt3: Into a 25 mL three-necked flask with magnetic stirring bar and condenser, ligand L3 (726 mg, 1.55 mmol, 1.0 eq), potassium chloroplatinate (677 mg, 1.63 mmol, 1.05 eq), n-tetrabutylammonium bromide (50 mg, 0.155 mmol, 0.1 eq) were added, and then the mixture was pumped with nitrogen, acetic acid (10 mL) was added under nitrogen protection, and then the mixture was bubbled with nitrogen for 30 min. The mixture was stirred at room temperature for 12 h, and then stirred in an oil bath at 120 °C for 48 h. After cooling to room temperature, the reaction was quenched with water, and then the mixture was extracted with dichloromethane and water three times, and then the organic phase was combined and dried over anhydrous sodium sulfate. The sample was spin-dried and column chromatography was used for separation, eluent: petroleum ether / dichloromethane = 2:1, finally the complex Pt3 was obtained as a green solid 284 mg, yield 28%.

[0104] 1 HNMR (500 MHz, CDC13) δ (ppm): 1.45 (s, 9H), 7.27-7.30 (m, 2H), 7.30-7.32 (m, 1H), 7.34-7.38 (m, 1H), 7.60 (d, J = 2.0 Hz, 1H), 7.62 (t, J = 7.5 Hz, 1H), 7.84 (d, J = 8.0 Hz, 1H), 7.89 (d, J = 7.5 Hz, 1H), 7.91-7.95 (m, 1H), 7.97 (d, J = 7.0 Hz, 1H), 8.01 (d, J = 8.5 Hz, 1H), 8.45 (dd, J = 7.5, 1.0 Hz, 1H), 8.72 (d, J = 6.0 Hz, 1H), 8.95 (d, J = 6.0 Hz, 1H). HRMS [M+H] + : 661.2.

[0105] Example 4: Synthesis of Pt4

[0106] Following the synthesis method of the complexes disclosed in Reference Example 1-3, the hydroxyl fragment was replaced by the methyl substituted counterpart fragment, to give Pt4, yellow solid 206 mg, yield 33%. HRMS [M+H] + : 636.1.

[0107] Example 5: Synthesis of Pt14

[0108] Following the synthesis method of the complexes disclosed in Reference Example 1-3, Pt14 was obtained, yellow solid 223 mg, yield 45%. HRMS [M+H] + : 716.2.

[0109] Example 6: Synthesis of Pt19

[0110] Following the synthesis method of the complexes disclosed in Reference Example 1-3, Pt19 was obtained, yellow solid 183 mg, yield 38%. HRMS [M+H] + : 690.1.

[0111] Example 7: Synthesis of Pt22

[0112] Following the synthesis method of the complexes disclosed in Reference Example 1-3, Pt22 was obtained, yellow solid 238 mg, yield 40%. HRMS [M+H] + : 692.2.

[0113] Example 8: Synthesis of Pt24

[0114] Pt24 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 241 mg, 41% yield. HRMS [M+H] Calcd for C64H96Pt 746.2 Found: 746.2. + :746.2.

[0115] Example 9: Synthesis of Pt35

[0116] Pt35 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 340 mg, 50% yield. HRMS [M+H] Calcd for C64H96Pt 678.2 Found: 678.2. + :678.2.

[0117] Example 10: Synthesis of Pt36

[0118] Pt36 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 214 mg, 42% yield. HRMS [M+H] Calcd for C64H96Pt 706.2 Found: 706.2. + :706.2.

[0119] Example 11: Synthesis of Pt38

[0120] Pt38 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 252 mg, 45% yield. HRMS [M+H] Calcd for C64H96Pt 690.2 Found: 690.2. + :690.2.

[0121] Example 12: Synthesis of Pt48

[0122] Pt48 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 313 mg, 53% yield. HRMS [M+H] Calcd for C64H96Pt 647.2 Found: 647.2. + :647.2.

[0123] Example 13: Synthesis of Pt52

[0124] Pt52 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 293 mg, 42% yield. HRMS [M+H] Calcd for C64H96Pt 699.2 Found: 699.2. + :699.2.

[0125] Example 14: Synthesis of Pt81

[0126] Pt81 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 188 mg, 39% yield. HRMS [M+H] Calcd for C64H96Pt 748.2 Found: 748.2. + :748.2.

[0127] Example 15: Synthesis of Pt100

[0128] Pt100 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 312 mg, 47% yield. HRMS [M+H] Calcd for C64H76N8O8P2Pt 1210.3 Found: 1210.3. + :838.3.

[0129] Example 16: Synthesis of Pt121

[0130] Pt121 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 241 mg, 41% yield. HRMS [M+H] Calcd for C64H76N8O8P2Pt 1210.3 Found: 1210.3. + :704.2.

[0131] Example 17: Synthesis of Pt148

[0132] Pt148 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 232 mg, 43% yield. HRMS [M+H] Calcd for C64H76N8O8P2Pt 1210.3 Found: 1210.3. + :762.3.

[0133] Example 18: Synthesis of Pt195

[0134] Pt195 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 250 mg, 48% yield. HRMS [M+H] Calcd for C64H76N8O8P2Pt 1210.3 Found: 1210.3. + :795.2.

[0135] Example 19: Synthesis of Pt212

[0136] Pt212 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 192 mg, 39% yield. HRMS [M+H] Calcd for C64H76N8O8P2Pt 1210.3 Found: 1210.3. + :916.4.

[0137] Example 20: Synthesis of Pt215

[0138] Pt215 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 163 mg, 49% yield. HRMS [M+H] Calcd for C64H76N8O8P2Pt 1210.3 Found: 1210.3. + :731.3.

[0139] Example 21: Synthesis of Pt246

[0140] Pt246 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 251 mg, 43% yield. HRMS [M+H] Calcd for C64H76N8O8P2Pt 1210.3 Found: 1210.3. + :896.3.

[0141] Example 22: Synthesis of Pt252

[0142] Pt252 was obtained following the synthetic procedure disclosed for the complex of reference example 1- example 3 as a yellow solid 113 mg, yield 29%. HRMS [M+H] Calcd for C42H42N6P2Pt 861.3 Found: 861.3. + :861.3.

[0143] Example 23: Synthesis of Pt260

[0144] Pt260 was obtained following the synthetic procedure disclosed for the complex of reference example 1- example 3 as a yellow solid 188 mg, yield 39%. HRMS [M+H] Calcd for C42H42N6P2Pt 910.4 Found: 910.4. + :910.4.

[0145] Example 24: Synthesis of Pt291

[0146] Pt291 was obtained following the synthetic procedure disclosed for the complex of reference example 1- example 3 as a yellow solid 188 mg, yield 39%. HRMS [M+H] Calcd for C42H42N6P2Pt 742.2 Found: 742.2. + :742.2.

[0147] Example 25: Synthesis of Pt300

[0148] Pt300 was obtained following the synthetic procedure disclosed for the complex of reference example 1- example 3 as a yellow solid 312 mg, yield 47%. HRMS [M+H] Calcd for C42H42N6P2Pt 721.1 Found: 721.1. + :721.1.

[0149] Example 26: Synthesis of Pt312

[0150] Pt312 was obtained following the synthetic procedure disclosed for the complex of reference example 1- example 3 as a yellow solid 241 mg, yield 41%. HRMS [M+H] Calcd for C42H42N6P2Pt 721.2 Found: 721.2. + :721.2.

[0151] Example 27: Synthesis of Pt313

[0152] Pt313 was obtained following the synthetic procedure disclosed for the complex of reference example 1- example 3 as a yellow solid 232 mg, yield 43%. HRMS [M+H] Calcd for C42H42N6P2Pt 692.2 Found: 692.2. + :692.2.

[0153] Example 28: Synthesis of Pt317

[0154] Pt317 was obtained following the synthetic procedure disclosed for the complex of reference example 1- example 3 as a yellow solid 250 mg, yield 48%. HRMS [M+H] Calcd for C42H42N6P2Pt 680.1 Found: 680.1. + :680.1.

[0155] Example 29: Synthesis of Pt318

[0156] Pt318 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 192 mg, 39% yield. HRMS [M+H] Calcd for C32H32N4O4Pt 637.1 Found: 637.2. + :837.2.

[0157] Example 30: Synthesis of Pt325

[0158] Pt325 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 356 mg, 46% yield. HRMS [M+H] Calcd for C33H32N4O4Pt 680.1 Found: 680.2. + :880.2.

[0159] Example 31: Synthesis of Pt336

[0160] Pt336 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 198 mg, 36% yield. HRMS [M+H] Calcd for C32H32N4O4Pt 783.2 Found: 783.2. + :783.2.

[0161] Example 32: Synthesis of Pt341

[0162] Pt341 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 270 mg, 36% yield. HRMS [M+H] Calcd for C32H32N4O4Pt 706.1 Found: 706.1. + :706.1.

[0163] Example 33: Synthesis of Pt343

[0164] Pt343 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 183 mg, 39% yield. HRMS [M+H] Calcd for C32H32N4O4Pt 740.1 Found: 740.1. + :740.1.

[0165] Example 34: Synthesis of Pt351

[0166] Pt351 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 185 mg, 58% yield. HRMS [M+H] Calcd for C32H32N4O4Pt 1004.3 Found: 1004.3. + :1004.3.

[0167] Example 35: Synthesis of Pt353

[0168] Pt353 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 192 mg, 49% yield. HRMS [M+H] Calcd for C32H32N4O4Pt 675.1 Found: 675.1. + :675.1.

[0169] Example 36: Synthesis of Pt354

[0170] Pt354 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 178 mg, 37% yield. HRMS [M+H] Calcd for C42H42N6O6P2Pt 878.2 Found: 878.2. + :851.2.

[0171] Example 37: Synthesis of Pt355

[0172] Pt355 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 208 mg, 46% yield. HRMS [M+H] Calcd for C43H44N6O6P2Pt 904.3 Found: 904.3. + :904.3.

[0173] Example 38: Synthesis of Pt356

[0174] Pt356 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 302 mg, 49% yield. HRMS [M+H] Calcd for C43H44N6O6P2Pt 902.4 Found: 902.4. + :902.4.

[0175] Example 39: Synthesis of Pt357

[0176] Pt357 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 285 mg, 35% yield. HRMS [M+H] Calcd for C42H42N6O6P2Pt 762.3 Found: 762.3. + :762.3.

[0177] Example 40: Synthesis of Pt358

[0178] Pt358 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 262 mg, 40% yield. HRMS [M+H] Calcd for C43H44N6O6P2Pt 797.3 Found: 797.3. + :797.3.

[0179] Example 41: Synthesis of Pt359

[0180] Pt359 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 281 mg, 44% yield. HRMS [M+H] Calcd for C44H46N6O6P2Pt 893.3 Found: 893.3. + :893.3.

[0181] Example 42: Synthesis of Pt360

[0182] Pt360 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 205 mg, 34% yield. HRMS [M+H] Calcd for C42H42N6O6P2Pt 776.3 Found: 776.3. + :776.3.

[0183] Example 43: Synthesis of Pt362

[0184] Pt362 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 197 mg, yield 33%. HRMS [M+H] Calcd for C42H42N6O6P2Pt 862.2 Found: 862.2. + : 855.2.

[0185] Example 44: Synthesis of Pt364

[0186] Pt364 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 182 mg, yield 32%. HRMS [M+H] Calcd for C42H42N6O6P2Pt 1012.2 Found: 1012.2. + : 1012.2.

[0187] Example 45: Synthesis of Pt365

[0188] Pt365 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 268 mg, yield 41%. HRMS [M+H] Calcd for C42H42N6O6P2Pt 888.3 Found: 888.3. + : 888.3.

[0189] Example 46: Synthesis of Pt366

[0190] Pt366 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 218 mg, yield 36%. HRMS [M+H] Calcd for C42H42N6O6P2Pt 756.1 Found: 756.1. + : 756.1.

[0191] Example 47: Synthesis of Pt367

[0192] Pt367 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 260 mg, yield 45%. HRMS [M+H] Calcd for C42H42N6O6P2Pt 994.4 Found: 994.4. + : 994.4.

[0193] Example 48: Synthesis of Pt368

[0194] Pt368 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 190 mg, yield 38%. HRMS [M+H] Calcd for C42H42N6O6P2Pt 864.2 Found: 864.2. + : 864.2.

[0195] Example 49: Synthesis of Pt369

[0196] Pt369 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 198 mg, yield 39%. HRMS [M+H] Calcd for C42H42N6O6P2Pt 854.2 Found: 854.2. + : 854.2.

[0197] Example 50: Synthesis of Pt370

[0198] Pt370 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 218 mg, 41% yield. HRMS [M+H] + : 787.3.

[0199] Example 51 : Synthesis of Pt371

[0200] Pt371 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 204 mg, 40% yield. HRMS [M+H] + : 852.2.

[0201] Example 52: Synthesis of Pt373

[0202] Pt373 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 276 mg, 41% yield. HRMS [M+H] + : 901.4.

[0203] Example 53: Synthesis of Pt376

[0204] Pt376 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 223 mg, 41% yield. HRMS [M+H] + : 946.3.

[0205] Example 54: Synthesis of Pt378

[0206] Pt378 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 232 mg, 38% yield. HRMS [M+H] + : 814.2.

[0207] Example 55: Synthesis of Pt381

[0208] Pt381 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 239 mg, 39% yield. HRMS [M+H] + : 776.2.

[0209] Example 56: Synthesis of Pt384

[0210] Pt384 was obtained following the synthetic procedure disclosed for the complexes of reference examples 1-3, yellow solid 181 mg, 32% yield. HRMS [M+H] + : 864.2.

[0211] Example 57: Synthesis of Pt385

[0212] Pt385 was obtained by the synthetic method of the complexes disclosed in Reference Example 1-Example 3, yellow solid 189 mg, yield 33%. HRMS [M+H] + : 979.2.

[0213] Theoretical calculation illustration

[0214] The present application optimizes the geometry structure of the ground state (S0) molecule by using density functional theory (DFT). The DFT calculation is performed by using B3LYP functional, wherein the C, H, O and N atoms use 6-31G(d) basis set, and the Pt atom uses LANL2DZ basis set. FIG. 1 is the HOMO, LUMO orbital distribution and energy level difference of the partial metal complexes of the present application. As can be seen from the calculation data in FIG. 1, the half-peak width of the complexes provided by the present application is 63-66 nm, which presents obvious charge transfer state. Pt1-Pt3 all present green light emission, and the emission peak shapes of Pt1 and Pt2 are consistent, and the maximum emission wavelengths are also similar, while Pt3 presents a certain degree of red shift. In Pt4, the methyl group is introduced at the para position of the nitrogen atom of the pyridine ring based on Pt1, and it can be seen that the LUMO orbital will also have a certain distribution on the methyl group.

[0215] Photophysical properties:

[0216] Table 1. Photophysical property data of partial metal complexes in dichloromethane solution

[0217] FIG. 2 is a room temperature emission spectrum diagram of platinum complex Pt1 in dichloromethane solution; FIG. 3 is a room temperature emission spectrum diagram of platinum complex Pt2 in dichloromethane solution; FIG. 4 is a room temperature emission spectrum diagram of platinum complex Pt3 in dichloromethane solution; for the complexes obtained by connecting different fragments with pyridine and carbazole structure, it can be seen from the above table 1 and the room temperature emission spectrum diagram of the platinum complex in dichloromethane solution and calculation in FIG. 2-FIG. 4 that different fragment structures will have a certain influence on the front orbital distribution, and such molecules present green light emission, and the light emission color will also produce red shift or blue shift according to the different fragments.

[0218] Manufacture of OLED device:

[0219] As a reference preparation mode of a device embodiment, the present application evaporates p-doped material on the surface of ITO glass or anode with a light emitting area of 2 mm x 2 mm size or co-evaporates p-doped material with a hole injection material to form a 5-100 nm hole injection layer (HIL) and a 5-200 nm hole transport layer (HTL) with a concentration of 1% to 50%, and then forms a 10-100 nm light emitting layer (EML) (which can contain the compound described in the present application) on the hole transport layer, forms a 20-200 nm electron transport layer (ETL) and a 50-200 nm cathode; if necessary, an electron blocking layer (EBL) is added between the HTL and the EML layer, and an electron injection layer (EIL) is added between the ETL and the cathode to manufacture an OLED device. The OLED described above is tested by a standard method. The device materials involved in the present application can be obtained by known synthesis methods if not specifically stated.

[0220] In a preferred embodiment, the structure of device example 1 provided by the present application is as follows:

[0221] ITO / HATCN (10 nm) / NPD (60 nm) / HTH-85 (5 nm) / Pt1: HTH-85: ETH-45 (25 nm) (mass ratio of Pt1: HTH-85: ETH-45 is 10:60:30) / ETH-5 (5 nm) / TrzPPh (40 nm) / LiQ (1 nm) / Al (100 nm).

[0222] Device examples 2-device examples 57 and comparative example 1 are prepared by using a similar structure as device example 1, with the only difference being that the complexes listed in Table 2 are used to replace Pt1 in device example 1, respectively. The light emitting properties of the comparative examples and device examples prepared above are tested by a standard method, and the data are shown in Table 2.

[0223] The device structure formula is as follows:

[0224] Table 2. Device light emitting property data table

[0225] As can be seen from Table 2, compared with Comparative Example 1, the device examples 1-57 prepared by the present application all exhibit good device performance in driving voltage, current efficiency and device lifetime, and in addition, the color purity of the device is also greatly improved. The performance improvement of each device example is based on the specific compound material of the present application having a small emission shoulder peak and at the same time having better electron transport ability. It can be seen that when it is prepared into an electronic device as a light-emitting layer material, it has higher current efficiency, device lifetime and color purity while reducing the driving voltage. It shows that the compound provided by the present application has certain commercial application value. In addition, the devices prepared by the present application are all deep blue light devices.

[0226] In a preferred embodiment, the structure of device example 58 provided by the present application is: ITO / HATCN (10 nm) / NPD (60 nm) / HTH-85 (5 nm) / platinum (II) complex: boron-containing compound: HTH-85: ETH-45 (25 nm) (mass ratio of Pt1: BN1-8: HTH-85: ETH-45 is 10: 1: 59: 30) / ETH-5 (5 nm) / TrzPPh (40 nm) / LiQ (1 nm) / Al (100 nm).

[0227] Device examples 59-75 are prepared by using a similar structure as device example 58, and the only difference is that the compounds listed in Table 3 are used to replace the platinum (II) complex and the boron-containing compound in device example 58. The device structure and light-emitting property data are shown in Table 3.

[0228] Table 3. Device structure and light-emitting property data table

[0229] As can be seen from Table 3, the complex of the present application can be used as a sensitizer, and when it is used as a sensitizing material together with a boron-containing compound as a light-emitting material on a device, the performance of each device is also significantly improved. The sensitized device structure after adding the boron-containing compound can further reduce the CIEy value, thereby improving the color purity of the device light-emitting color. It further shows that the compound provided by the present application has certain commercial application value.

[0230] The applicant declares that the above description is only a specific embodiment of the present application, but the protection scope of the present application is not limited thereto. It should be understood by those skilled in the art that any changes or replacements within the technical scope disclosed by the present application can be easily thought of by those skilled in the art, and all fall within the protection scope and disclosure scope of the present application.

Claims

1. A metal platinum (II) complex characterized in that, having the structure of Formula I: wherein ring A represents a C3-C30 nitrogen heteroaryl group, X1, X2are each independently selected from N, C; R 1 , R 2 , R 3 , R 4 , R 5 each independently represent mono-substitution, di-substitution, tri-substitution, tetra-substitution, or no substitution; R 1 , R 2 , R 3 , R 4 , R 5 each independently represent any one of hydrogen, deuterium, cyano, halogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C1-C30 alkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C5-C30 heteroaryl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C1-C30 arylamine, substituted or unsubstituted C1-C30 alkylsilyl, substituted or unsubstituted C6-C30 arylsilyl, substituted or unsubstituted C1-C30 siloxane group; when containing substitution, the substituent is selected from deuterium, cyano, halogen, C1-C14 alkyl, C3-C14 cycloalkyl, C6-C18 aryl, C5-C18 heteroaryl.

2. The metal platinum (II) complex according to claim 1, characterized in that, R 1 represents any of hydrogen, deuterium, cyano, fluorine, C1-C14 alkyl, C1-C14 fluoroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted C3-C30 silyl, substituted or unsubstituted C1-C10 oxyalkyl, substituted or unsubstituted C3-C30 siloxanyl; when containing a substituent, said substituent is selected from the group consisting of deuterium, cyano, fluorine, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl, pyridyl.

3. The metal platinum (II) complex of claim 1, wherein R 2 represents any of hydrogen, deuterium, C1-C4 alkyl; R 3 represents any of hydrogen, deuterium, cyano, fluorine, C1-C14 alkyl, C1-C14 fluoroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted cycloamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, C3-C30 silyl, C3-C30 arylsilyl, C1-C10 oxyalkyl, diphenylamino, substituted or unsubstituted C3-C30 siloxanyl; when containing a substituent, said substituent is selected from the group consisting of deuterium, cyano, fluorine, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl.

4. The metal platinum (II) complex of claim 1, wherein R 4 represents any of hydrogen, deuterium, cyano, fluorine, C1-C14 alkyl, C1-C14 fluoroalkyl, substituted or unsubstituted C3-C12 cycloalkyl, substituted or unsubstituted C3-C12 cycloalkylamine, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted pyridyl, substituted or unsubstituted C3-C30 silyl, C1-C10 oxyalkyl, C1-C10 siloxanyl; when containing a substituent, said substituent is selected from the group consisting of deuterium, cyano, fluorine, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl.

5. The metal platinum (II) complex of claim 1, wherein R 5 represents any of hydrogen, deuterium, cyano, fluorine, C1-C14alkyl, C1-C14deuteroalkyl, substituted or unsubstituted C6-C30aryl, pyridyl, substituted or unsubstituted C1-C10oxyalkyl, substituted or unsubstituted C1-C10siloxanyl; when containing a substituent, said substituent is selected from the group consisting of deuterium, methyl, ethyl, propyl, isopropyl, tert-butyl, phenyl.

6. The metal platinum (II) complex of claim 1, wherein The complex of formula I has one of the structures of formula Pt-(I), Pt-(II) or Pt-(III): Among them, R 1 R 2 R 3 R 4 R 5 R as described in claim 1 1 R 2 R 3 R 4 R 5 The substitution situation is the same; R 6 It is represented as hydrogen, deuterium, C1–C24 alkyl, substituted or unsubstituted C6–C30 aryl; when it contains a substituent, the substituent is selected from deuterium, fluorine, C1–C10 alkyl, C6–C18 aryl.

7. The metal platinum (II) complex according to any one of claims 1 to 6, characterized in that, The metal platinum (II) complex is selected from any one of the chemical structures shown below, wherein "D" represents deuterium:

8. Use of the metal platinum (II) complex according to any one of claims 1 to 7 for the production of an electronic device.

9. Use according to claim 8, characterized in that, The electronic device includes an organic electroluminescence device, an organic integrated circuit, an organic field-effect transistor, an organic thin-film transistor, an organic light-emitting transistor, an organic solar cell, an organic optical detector, an organic photo-receptor, an organic field-quench device, a light-emitting electrochemical cell, and an organic laser diode.

10. An organic electroluminescent device, characterized by comprising The organic electroluminescence device includes a cathode, an anode, and an organic functional layer interposed therebetween; the organic functional layer contains the metal platinum (II) complex according to any one of claims 1 to 7.

11. The organic electroluminescent device according to claim 10, wherein The organic functional layer contains a light-emitting layer, and the light-emitting layer contains the metal platinum (II) complex according to any one of claims 1 to 7.

12. The organic electroluminescent device according to claim 11, characterized in that, The light-emitting layer further comprises a fluorescent dopant material; the fluorescent dopant material is selected from any one or more of the compounds represented by formula (BN1) to formula (BN5): wherein Y is O, S, Se or NR 300 ; Y 1 , Y 2 , Y 3 , Y 4 each independently represents O, S, Se or N; R b -R e each independently represents mono-, di-, tri-, tetra- or non-substitution; R b -R e each independently is selected from the group consisting of hydrogen, deuterium, N, C1–C30alkyl, C6–C30aryl and; said R a , R7-R 12 each independently represents is selected from the group consisting of hydrogen, deuterium, N, C1–C30alkyl, C6–C30aryl, C6–C30N heteroaryl and.

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

14. The organic optoelectronic device according to claim 13, characterized in that The organic light-emitting functional layer further comprises a fluorescent dopant material; the fluorescent dopant material is selected from any one or more of the compounds represented by formula (BN1) to formula (BN5): wherein Y is O, S, Se or NR 300 ; Y 1 , Y 2 , Y 3 , Y 4 each independently represents O, S, Se or N; R b -R e each independently represents mono-, di-, tri-, tetra- or non-substitution; R b -R e each independently is selected from the group consisting of hydrogen, deuterium, N, C1–C30alkyl, C6–C30aryl and; said R a , R7-R 12 each independently represents is selected from the group consisting of hydrogen, deuterium, N, C1–C30alkyl, C6–C30aryl, C6–C30N heteroaryl and.

15. A composition characterized in that, The composition contains the metal platinum (II) complex according to any one of claims 1 to 7.

16. The composition of claim 15, wherein, The composition comprises a fluorescent dopant material; the fluorescent dopant material is selected from any one or more of the compounds represented by formula (BN1) to formula (BN5): wherein Y is O, S, Se or NR 300 ; Y 1 , Y 2 , Y 3 , Y 4 each independently represents O, S, Se or N; R b -R e each independently represents mono-, di-, tri-, tetra- or non-substitution; R b -R e each independently is selected from the group consisting of hydrogen, deuterium, N, C1–C30alkyl, C6–C30aryl and; said R a , R7-R 12 each independently represents is selected from the group consisting of hydrogen, deuterium, N, C1–C30alkyl, C6–C30aryl, C6–C30N heteroaryl and.

17. A formulation characterized in that, The preparation contains the metal platinum (II) complex according to any one of claims 1 to 7 and at least one solvent.

18. A display or illumination device, characterized in that The device contains one or more of the organic electroluminescence devices according to any one of claims 10 to 12.

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