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CN114621296B - Organometallic complex, preparation, organic photoelectric device and display or lighting device - Google Patents

Organometallic complex, preparation, organic photoelectric device and display or lighting device Download PDF

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CN114621296B
CN114621296B CN202210336815.1A CN202210336815A CN114621296B CN 114621296 B CN114621296 B CN 114621296B CN 202210336815 A CN202210336815 A CN 202210336815A CN 114621296 B CN114621296 B CN 114621296B
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organometallic complex
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CN114621296A (en
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叶绪兵
申屠晓波
吴空物
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Zhejiang Huadisplay Optoelectronics Co Ltd
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Zhejiang Huadisplay Optoelectronics Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0086—Platinum compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

The invention provides an organometallic complex, a preparation, an organic photoelectric device and a display or lighting device. The structure is shown as formula (I)The platinum metal compound is applied to an organic photoelectric device, particularly an organic electroluminescent device, and can improve current efficiency, reduce operating voltage of the device and obtain the long-life organic photoelectric device.

Description

Organometallic complex, preparation, organic photoelectric device and display or lighting device
Technical Field
The invention relates to an organic metal complex, in particular to an organic metal complex, a preparation, an organic photoelectric device and a display or lighting device, and belongs to the field of organic photoelectricity.
Background
The organic light-emitting diode (OLED) is used as a novel display technology, has the unique advantages of self-luminescence, wide visual angle, low energy consumption, high efficiency, thinness, rich colors, high response speed, wide applicable temperature range, low driving voltage, flexible and bendable transparent display panel manufacturing, environment friendliness and the like, can be applied to flat panel displays and new-generation illumination, and can also be used as a backlight source of an LCD.
Since the end of the 80 th century, organic electroluminescent devices have been industrially used, and OLED luminescence is classified into fluorescence luminescence and phosphorescence, and it is theoretically presumed that the ratio of singlet excited state to triplet excited state due to carrier recombination is 1:3, so that when a small molecular fluorescent material is used, only 25% of the total energy available for luminescence is lost, and the remaining 75% of the energy is lost due to the non-luminescence mechanism of the triplet excited state, and therefore, it is generally considered that the internal quantum efficiency limit of the fluorescent material is 25%. In the professor Forrest, 1998, et al found that triplet phosphorescence can be utilized at room temperature, the upper limit of the original internal quantum efficiency is raised to 100%, the triplet phosphors are often complexes composed of heavy metal atoms, and the strong spin-orbit coupling effect is utilized to enable the triplet energy which is originally forbidden to emit light in a phosphorescence mode, so that the quantum efficiency is also greatly raised.
The light-emitting layer in the current organic OLED device almost entirely uses a host-guest light-emitting system mechanism, i.e., a guest light-emitting material is doped in a host material, and generally, the energy of the organic host material is larger than that of the guest material, i.e., energy is transferred from the host to the guest, so that the guest material is excited to emit light. The phosphorescent organic host materials commonly used have a high triplet energy level, and when the organic host material is excited by an electric field, triplet energy can be efficiently transferred from the organic host material to the guest phosphorescent material. Common organic guest materials are iridium and platinum metal compounds. Currently, iridium metal compounds have become mainstream in commercial OLED materials, but development of platinum complex materials and devices still has some technical difficulties, such as high efficiency, long service life and lower operating voltage of OLED.
Disclosure of Invention
The object of the present invention is to provide an organometallic complex, a formulation, an organic optoelectronic device and a display or lighting device, in particular an organic electroluminescent diode.
The invention provides an organic metal complex, the structure of which is shown as the formula (I)
In formula (I), cy1 and Cy2 are each independently selected from C6-C60 aryl or C1-C60 heteroaryl. R is R 1 、R 2 、R 3 、R 4 、R 5 Each independently selected from the group consisting of hydrogen, deuterium, halogen, C1-C18 alkyl, C1-C18 alkoxy, C1-C18 alkylsilyl, C6-C40 substituted or unsubstituted aryl, C1-C40 heteroaryl, C1-C60 substituted or unsubstituted heterospiro, C1-C60 substituted or unsubstituted spiroA substituted or unsubstituted aryl ether group, a substituted or unsubstituted heteroaryl ether group, a substituted or unsubstituted arylamine group, a substituted or unsubstituted heteroarylamine group, a substituted or unsubstituted arylsilyl group, a substituted or unsubstituted heteroarylsilicon group, a substituted or unsubstituted aryloxysilyl group, a substituted or unsubstituted arylacyl group, a substituted or unsubstituted heteroarylacyl group, or a substituted or unsubstituted phosphinyl group;
all groups may be partially deuterated or fully deuterated;
x, X1 and X2 are each independently selected from C or N;
y is selected from O, S or C.
Preferably, two atoms attached to the metal Pt form covalent bonds and two form coordination bonds.
Preferably, the organometallic complex of formula (I) is selected from one of the following representative structures:
the present invention further provides a formulation comprising the organometallic complex of the present invention and at least one solvent.
Preferably, the solvent is an unsaturated hydrocarbon solvent, a halogenated saturated hydrocarbon solvent, a halogenated unsaturated hydrocarbon solvent, an ether solvent or an ester solvent,
wherein the unsaturated hydrocarbon solvent is preferably toluene, xylene, mesitylene, tetrahydronaphthalene, decalin, dicyclohexyl, n-butylbenzene, sec-butylbenzene or tert-butylbenzene;
the halogenated saturated hydrocarbon solvent is preferably carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane;
the halogenated unsaturated hydrocarbon solvent is preferably chlorobenzene, dichlorobenzene or trichlorobenzene;
the ether solvent is preferably tetrahydrofuran or tetrahydropyran;
the ester solvent is preferably an alkyl benzoate.
The present invention also provides an organic photoelectric device, comprising:
a first electrode;
a second electrode facing the first electrode;
an organic functional layer sandwiched between the first electrode and the second electrode;
wherein the organic functional layer comprises the organometallic complex according to the invention.
The invention also provides an organic photoelectric device, which comprises a cathode layer, an anode layer and an organic layer, wherein the organic layer comprises at least one layer of a hole injection layer, a hole transmission layer, a light emitting layer or an active layer, an electron injection layer and an electron transmission layer, and any layer of the device contains the compound.
Preferably, the light-emitting layer contains the organometallic complex and a corresponding host material, and the host material is not limited at all, wherein the mass percentage of the organometallic complex is 1% to 50%.
Preferably, the organic optoelectronic device is an organic photovoltaic device, an Organic Light Emitting Device (OLED), an Organic Solar Cell (OSC), an electronic paper (e-paper), an Organic Photoconductor (OPC), an Organic Thin Film Transistor (OTFT), or an organic memory device (Organic Memory Element).
The invention further provides a display or lighting device comprising the organic optoelectronic device.
The invention has the beneficial effects that:
the organic metal complex has good thermal stability, and the electron transmission performance is improved by introducing benzofuran [2,3-c ] pyridine, so that the device efficiency is improved. The organic metal complex has better electron and hole receiving capability, can promote energy transmission between a host and an object, and is particularly characterized in that the organic electroluminescent device manufactured by using the organic metal complex as a functional layer, especially as a luminescent layer, has improved current efficiency, reduced lighting voltage and longer service life, and indicates that most of energy is effectively transferred to the organic metal complex for luminescence rather than heating after the electron and the hole are compounded.
Drawings
FIG. 1 is a schematic representation of the HOMO and LUMO orbital distributions of Compound 1 of the present invention;
FIGS. 2a-b are top and side views, respectively, of a Pt complex based on triphenylphosphine oxide coordination units;
fig. 3 is a view showing a structure of an organic electroluminescent diode device according to the present invention, in which 110 represents a substrate, 120 represents an anode, 130 represents a hole injection layer, 140 represents a hole transport layer, 150 represents a light emitting layer, 160 represents a hole blocking layer, 170 represents an electron transport layer, 180 represents an electron injection layer, and 190 represents a cathode.
Detailed Description
The present invention will be described in further detail with reference to specific embodiments in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the specific embodiments described herein are for purposes of illustration only and are not intended to limit the scope of the invention.
In a preferred embodiment of the present invention, the OLED device of the present invention comprises a hole transporting layer, and the hole transporting material may preferably be selected from known or unknown materials, particularly preferably from the following structures, but does not represent the present invention limited to the following structures:
in a preferred embodiment of the present invention, the hole transport layer comprised in the OLED device of the present invention comprises one or more p-type dopants. The preferred p-type dopants of the present invention are of the following structure, but are not meant to limit the invention to the following structure:
in a preferred embodiment of the present invention, the electron transport layer may be selected from at least one of the following compounds, but does not represent the present invention limited to the following structures:
the present invention develops a novel platinum metal compound by introducing a tetrapod ligand unit containing triphenylphosphine oxide (fig. 1). The LUMO orbit is found to be delocalized on triphenylphosphine oxide and a benzene ring connected with the phosphine oxide, so that the electron mobility of the phosphine oxide can be effectively improved, the recombination efficiency of holes and electrons in a luminescent layer of the device is increased, and the luminescent efficiency of the device is improved. The platinum metal compound is applied to an organic photoelectric device, particularly an organic electroluminescent device, so that the current efficiency can be improved, the operating voltage of the device can be reduced, and the long-life organic photoelectric device can be obtained. In addition, as shown in fig. 2a-b, two benzene rings based on triphenylphosphine oxide are respectively directed to two sides of a Pt coordination plane, which is beneficial to inhibiting interaction between Pt complex molecules and inhibiting triplet-triplet quenching, thereby improving device efficiency.
The present invention relates to an organometallic complex comprising a preparation of the compound of the formula (I) with one or more solvents, and the solvents used are not particularly limited, and unsaturated hydrocarbon solvents such as toluene, xylene, mesitylene, tetrahydronaphthalene, decalin, bicyclohexane, n-butylbenzene, sec-butylbenzene, tert-butylbenzene, halogenated saturated hydrocarbon solvents such as carbon tetrachloride, chloroform, methylene chloride, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane, bromocyclohexane, halogenated unsaturated hydrocarbon solvents such as chlorobenzene, dichlorobenzene, trichlorobenzene, ether solvents such as tetrahydrofuran, tetrahydropyran, and ester solvents such as alkyl benzoate, which are well known to those skilled in the art, may be used. The preparation is directly used for preparing an organic photoelectric device.
In the present invention, the organic photoelectric device is an anode formed by vapor deposition of a metal or an oxide having conductivity and an alloy thereof on a substrate by a sputtering method, an electron beam evaporation method, a vacuum vapor deposition method, or the like; evaporating a hole injection layer, a hole transmission layer, a luminescent layer, a hole blocking layer and an electron transmission layer on the surface of the prepared anode in sequence, and evaporating a cathode. The organic electronic device is manufactured by evaporating the cathode, the organic layer and the anode on the substrate except the method. The organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron transport layer, and the like. The organic layer is prepared by adopting a macromolecular material to replace an evaporation method according to solvent engineering (spin-coating), tape-casting, doctor-blading (doctor-blading), screen Printing (Screen-Printing), ink-jet Printing or Thermal Imaging (Thermal-Imaging) and the like, so that the number of device layers can be reduced.
The materials used in the organic electroluminescent device according to the present invention may be classified as top emission, bottom emission or double-sided emission. The organic electroluminescent device compound according to the embodiment of the present invention can be applied to organic solar cells, illuminated OLEDs, flexible OLEDs, organic photoreceptors, organic thin film transistors, and other electroluminescent devices in a similar principle as organic light emitting devices.
Examples
Hereinafter, the general synthetic procedure for the guest compounds of formula (I) is as follows:
ligand 1
Will K 2 PtCl 4 (2.2 mmol), ligand 1 (2.4 mmol), CHCl 3 (100 mL) and AcOH (100 mL) were added to a two-necked round bottom flask, then heated to reflux for 120 hours, the heating was stopped, cooled to room temperature, and the solvent was removed. Dissolving the solid in dichloromethane, passingSilica gel short column. Removing the solvent under the condition of reduced pressure, washing the solid obtained by concentration by methanol and petroleum ether in sequence to obtain the final target product with the yield of 30-56%.
The preparation method of the platinum metal compound, i.e., the guest compound, and the light emitting performance of the device are explained in detail in connection with the following examples. These are merely examples of embodiments of the present invention and thus the scope of the present invention is not limited thereto. Ligand 1 was obtained by custom synthesis.
Example 1: synthesis of Compound 1
Referring to the general synthetic route, the yield of the final product was 34%. Mass spectrum m/z, theory 729.11; actual measurement value M+H:730.41.
example 2: synthesis of Compound 2
Referring to the general synthetic route, the yield of the final product was 42%. Mass spectrum m/z, theory 841.24; actual measurement value M+H:842.28.
example 3: synthesis of Compound 3
Referring to the general synthetic route, the yield of the final product was 44%. Mass spectrum m/z, theory 801.15; actual measurement value M+H:802.24.
example 4: synthesis of Compound 4
Referring to the general synthetic route, the yield of the final product was 42%. Mass spectrum m/z, theory 730.11; actual measurement value M+H:731.19.
example 5: synthesis of Compound 5
Referring to the general synthetic route, the yield of the final product was 44%. Mass spectrum m/z, theory 811.23; actual measurement value M+H:812.24.
example 6: synthesis of Compound 6
Referring to the general synthetic route, the yield of the final product was 31%. Mass spectrum m/z, theory 991.32; actual measurement value M+H:992.42.
example 7: synthesis of Compound 7
Referring to the general synthetic route, the yield of the final product was 33%. Mass spectrum m/z, theory 904.29; actual measurement value M+H:905.37.
example 8: synthesis of Compound 8
Referring to the general synthetic route, the yield of the final product was 38%. Mass spectrum m/z, theory 1091.41; actual measurement value M+H:1092.45.
example 9: synthesis of Compound 9
Referring to the general synthetic route, the yield of the final product was 42%. Mass spectrum m/z, theory 1141.33; actual measurement value M+H:1142.38.
example 10: synthesis of Compound 10
Referring to the general synthetic route, the yield of the final product was 42%. Mass spectrum m/z, theory 1099.29; actual measurement value M+H:1100.36.
manufacturing of OLED device:
evaporating a p-doped material on the surface or anode of ITO glass with a light emitting area of 2mm x 2mm or co-evaporating the p-doped material with the compound in the table at a concentration of 1% -50% to form a Hole Injection Layer (HIL) of 5-100nm, a Hole Transport Layer (HTL) of 5-200nm, then forming a light emitting layer (EML) of 10-100nm (which may contain the compound) on the hole transport layer, and finally forming an Electron Transport Layer (ETL) of 20-200nm and a cathode of 50-200nm with the compound in sequence, adding an Electron Blocking Layer (EBL) between the HTL and the EML layer if necessary, and adding an Electron Injection Layer (EIL) between the ETL and the cathode to manufacture an organic light emitting device. The OLEDs are tested by standard methods and are listed in table 1.
In the specific embodiment, the structure of the bottom emission OLED device is that the HIL is HT-1:P-3 (95:5, v/v%) and the thickness is 10 nanometers on glass containing ITO; HTL is HT-1 and has a thickness of 90 nanometers; EBL is HT-8, thickness is 10 nm, EML is main material: organometallic complex (90:10, v/v%), thickness is 35 nm, ETL is ET-13: liQ (50:50, v/v%) was 35 nm thick, and then the evaporation cathode Al was 70 nm.
Characteristics of current efficiency, voltage, and lifetime according to the above embodiment are shown in table 1 below.
TABLE 1
As can be seen from Table 1, the introduction of triphenylphosphine oxide on the ligand structure, device examples 1 to 10 showed good device performance, demonstrating that the organometallic complex provided by the invention has a certain application value.
The foregoing is only a preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art, who is within the scope of the present invention, should make equivalent substitutions or modifications according to the technical scheme of the present invention and the inventive concept thereof, and should be covered by the scope of the present invention.

Claims (8)

1. An organometallic complex, characterized in that said organometallic complex is selected from the group consisting of:
2. a formulation comprising the organometallic complex of claim 1 and at least one solvent.
3. A formulation according to claim 2, wherein the solvent is an unsaturated hydrocarbon solvent, halogenated saturated hydrocarbon solvent, halogenated unsaturated hydrocarbon solvent, ether solvent or ester solvent; the unsaturated hydrocarbon solvent is toluene, xylene, mesitylene, tetrahydronaphthalene, n-butylbenzene, sec-butylbenzene or tert-butylbenzene, the halogenated saturated hydrocarbon solvent is carbon tetrachloride, chloroform, dichloromethane, dichloroethane, chlorobutane, bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane, chlorocyclohexane or bromocyclohexane, the halogenated unsaturated hydrocarbon solvent is chlorobenzene, dichlorobenzene or trichlorobenzene, the ether solvent is tetrahydrofuran or tetrahydropyran, and the ester solvent is alkyl benzoate.
4. An organic optoelectronic device, comprising:
a first electrode;
a second electrode facing the first electrode;
the light-emitting layer is clamped between the first electrode and the second electrode;
wherein the light-emitting layer comprises the organometallic complex according to claim 1.
5. The organic optoelectronic device according to claim 4, wherein the organic optoelectronic device is an organic light emitting device.
6. An organic photoelectric element comprising a cathode layer, an anode layer and an organic layer, wherein the organic layer comprises at least one of a hole injection layer, a hole transport layer, a light emitting layer or an active layer, an electron injection layer and an electron transport layer, and the organic photoelectric element is characterized in that the light emitting layer contains the organometallic complex according to claim 1.
7. The organic photoelectric element according to claim 6, wherein the light-emitting layer contains the organometallic complex according to claim 1 and a host material, wherein the mass percentage of the organometallic complex is 1% to 50%, and the host material is not limited.
8. A display or lighting device comprising the organic photovoltaic element according to claim 6.
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Publication number Priority date Publication date Assignee Title
CN104232076A (en) * 2013-06-10 2014-12-24 代表亚利桑那大学的亚利桑那校董会 Phosphorescent tetradentate metal complexes having modified emission spectra
CN107266505A (en) * 2017-06-15 2017-10-20 浙江工业大学 Tetradentate ring metal platinum (II) complex phosphorescence luminescent material
CN111518142A (en) * 2020-06-10 2020-08-11 浙江工业大学 Tetradentate cyclic metal platinum(II) complexes based on carboxyl coordination and containing pyridyl acridine and their applications
CN112409417A (en) * 2019-08-23 2021-02-26 三星显示有限公司 Organometallic compound and organic light-emitting device including the same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104232076A (en) * 2013-06-10 2014-12-24 代表亚利桑那大学的亚利桑那校董会 Phosphorescent tetradentate metal complexes having modified emission spectra
CN107266505A (en) * 2017-06-15 2017-10-20 浙江工业大学 Tetradentate ring metal platinum (II) complex phosphorescence luminescent material
CN112409417A (en) * 2019-08-23 2021-02-26 三星显示有限公司 Organometallic compound and organic light-emitting device including the same
CN111518142A (en) * 2020-06-10 2020-08-11 浙江工业大学 Tetradentate cyclic metal platinum(II) complexes based on carboxyl coordination and containing pyridyl acridine and their applications

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