WO2017080316A1 - 用于印刷电子的组合物及其在电子器件中的应用 - Google Patents
用于印刷电子的组合物及其在电子器件中的应用 Download PDFInfo
- Publication number
- WO2017080316A1 WO2017080316A1 PCT/CN2016/099783 CN2016099783W WO2017080316A1 WO 2017080316 A1 WO2017080316 A1 WO 2017080316A1 CN 2016099783 W CN2016099783 W CN 2016099783W WO 2017080316 A1 WO2017080316 A1 WO 2017080316A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- printing
- composition
- organic
- atoms
- Prior art date
Links
- 0 NIN1C2C1*CCC*2 Chemical compound NIN1C2C1*CCC*2 0.000 description 6
- XVNHCXMTNRRRDE-UHFFFAOYSA-N CC(C)(C1=CC=CCC1)C1=NCN(C2(C)c3ccccc3)C2=C1 Chemical compound CC(C)(C1=CC=CCC1)C1=NCN(C2(C)c3ccccc3)C2=C1 XVNHCXMTNRRRDE-UHFFFAOYSA-N 0.000 description 1
- LGYXANVWACBXST-UHFFFAOYSA-N CC(C1)C=Cc2c1c(C=CCC1)c1c1ccccc21 Chemical compound CC(C1)C=Cc2c1c(C=CCC1)c1c1ccccc21 LGYXANVWACBXST-UHFFFAOYSA-N 0.000 description 1
- FJHQXKYKAAOMSA-UHFFFAOYSA-N CC12NC=CN=C1C=CC=C2 Chemical compound CC12NC=CN=C1C=CC=C2 FJHQXKYKAAOMSA-UHFFFAOYSA-N 0.000 description 1
- MRRCEXCXCFEBBI-UHFFFAOYSA-N CC1NC2=CC=CNC2(C)C=C1 Chemical compound CC1NC2=CC=CNC2(C)C=C1 MRRCEXCXCFEBBI-UHFFFAOYSA-N 0.000 description 1
- UVOUSDCALWZECZ-UHFFFAOYSA-N CC1NC=CN=C1 Chemical compound CC1NC=CN=C1 UVOUSDCALWZECZ-UHFFFAOYSA-N 0.000 description 1
- UFWDOFZYKRDHPB-UHFFFAOYSA-N c(cc1)cc(c2ccccc22)c1[n]2-c1cccc(-c2nc(-c3cc(-[n]4c(cccc5)c5c5c4cccc5)ccc3)ccc2)c1 Chemical compound c(cc1)cc(c2ccccc22)c1[n]2-c1cccc(-c2nc(-c3cc(-[n]4c(cccc5)c5c5c4cccc5)ccc3)ccc2)c1 UFWDOFZYKRDHPB-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N c1cc2cccnc2nc1 Chemical compound c1cc2cccnc2nc1 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N c1cncnc1 Chemical compound c1cncnc1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N c1ncncn1 Chemical compound c1ncncn1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/033—Printing inks characterised by features other than the chemical nature of the binder characterised by the solvent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
- C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/322—Pigment inks
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/36—Inkjet printing inks based on non-aqueous solvents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/52—Electrically conductive inks
-
- 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
-
- 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
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
- C09K11/54—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing zinc or cadmium
-
- 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
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
- C09K11/56—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing sulfur
- C09K11/562—Chalcogenides
- C09K11/565—Chalcogenides with zinc cadmium
-
- 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
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
- C09K11/88—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing selenium, tellurium or unspecified chalcogen elements
- C09K11/881—Chalcogenides
- C09K11/883—Chalcogenides with zinc or cadmium
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
- H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
-
- 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
-
- 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
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- 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
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/20—Delayed fluorescence emission
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/115—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising active inorganic nanostructures, e.g. luminescent quantum dots
-
- 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
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/10—Deposition of organic active material
- H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
- H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- 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
Definitions
- the present invention relates to a composition suitable for printing electronics and its use in printed electronic devices, particularly in electroluminescent devices.
- the organic light-emitting diode which is a new-generation display technology
- OLED organic light-emitting diode
- FMM fine mask
- Low yield In order to solve the above problems, techniques for realizing high-resolution full-color display using a printing process have received increasing attention. For example, inkjet printing can produce functional material films in a large area and at low cost. Compared with traditional semiconductor production processes, inkjet printing has low energy consumption, low water consumption, and environmental protection, and is a production technology with great advantages and potential.
- QLED quantum dot light-emitting diode
- Organic semiconductor materials have gained widespread attention and significant progress in their use in electronic and optoelectronic devices due to their solution processability.
- Solution processability allows the organic functional material to form a thin film of the functional material in the device by certain coating and printing techniques. Such a technology can effectively reduce the processing cost of electronic and optoelectronic devices, and meet the process requirements of large-area preparation.
- KATEEVA discloses an ester solvent-based organic small molecule material ink for printing OLEDs (US2015044802A1)
- UNIVERSALDISPLAYCORPORATION discloses a A printable organic small molecular material ink based on an aromatic ketone or an aromatic ether solvent (US20120205637)
- SEIKOEPSON CORPORATION discloses a printable organic polymer material ink based on a substituted benzene derivative solvent.
- printing inks involving organic functional materials are: CN102408776A, CN103173060A, CN103824959A, CN1180049C, CN102124588B, US2009130296A1, US2014097406A1, and the like.
- Quantum dots are nano-sized semiconductor materials with quantum confinement effects. When stimulated by light or electricity, quantum dots emit fluorescence with specific energy. The color (energy) of fluorescence is determined by the chemical composition and size of quantum dots. Therefore, the control of the size and shape of quantum dots can effectively regulate its electrical and optical properties.
- countries are studying the application of quantum dots in full color, mainly in the display field.
- quantum light-emitting devices QLEDs
- QLEDs quantum light-emitting devices
- NanocoTechnologies Ltd. discloses a method of printing a printable ink formulation comprising nanoparticles (CN101878535B).
- Printable nanoparticle inks and corresponding nanoparticle-containing films are obtained by selecting suitable solvents such as toluene and dodecyl selenol; Samsung Electronics discloses a quantum dot ink for inkjet printing ( US8765014B2).
- the ink contains a concentration of quantum dot material, an organic solvent, and an alcohol polymer additive having a high viscosity.
- a quantum dot film is obtained by printing the ink, and a quantum dot electroluminescent device is prepared;
- QD Vision QDVision, Inc. discloses a quantum dot ink preparation comprising a host material and a quantum dot material.
- an additive US2010264371A1.
- these quantum dot inks contain Its additives, such as alcohol polymers.
- additives such as alcohol polymers.
- polymer additives with insulating properties tends to reduce the charge transport capability of the film, which has a negative impact on the photoelectric performance of the device, and limits its wide application in optoelectronic devices.
- One of the objects of the present invention is to provide a composition for electronic printing.
- a composition for printing electrons comprising at least one functional material and a solvent system comprising at least one organic solvent, the organic solvent comprising at least one organic based on heteroaromatic and having the general formula (I) Solvent:
- Ar 1 is a heteroaromatic ring having 5 to 10 carbon atoms, n is an integer greater than or equal to 0, and R is a substituent characterized by being heteroaromatic-based and having an organic solvent of the formula (I)
- the boiling point is ⁇ 150 ° C and can be evaporated from the solvent system to form a film containing the inorganic nanomaterial.
- the composition for printing electrons has a viscosity based on a heteroaromatic and organic solvent of the formula (I) at 25 ° C in the composition for printing electrons described above. , in the range of 1cPs to 100cPs.
- the composition for printing electrons is used in a composition for printing electrons as described above, the organic solvent based on heteroaromatic and having the general formula (I) at 25 ° C Surface tension, in the range of 19 dyne/cm to 50 dyne/cm.
- the composition for printing electrons in the composition for printing electrons described above, the organic solvent based on heteroaromatic and having the general formula (I) has a general formula selected from the group consisting of The structure shown in either one:
- X is CR 1 or N
- At least one X or Y in each formula is a non-C atom (so-called hetero atom);
- composition for printing electrons in the composition for printing electrons described above, the Ar 1 in the formula (I) is selected from any one of the following structural units:
- R in the formula (I) is selected from the group consisting of a linear alkyl group having 1 to 20 C atoms, an alkoxy group or a thioalkyl group.
- the heteroaromatic based organic solvent having the general formula (I) is selected from the group consisting of: 2-phenylpyridine, 3-phenylpyridine, 4 -(3-phenylpropyl)pyridine, quinoline, isoquinoline, 8-hydroxyquinoline, methyl 2-furancarboxylate, ethyl 2-furancarboxylate or a mixture of any two or more thereof.
- the solvent system may be a mixed solvent further comprising at least one other solvent, and the Organic of formula (I) The solvent accounts for more than 50% of the total weight of the mixed solvent.
- the composition for printing electrons is in the composition for printing electrons described above, the functional material being an inorganic nano material.
- the composition for printing electrons is used in a composition for printing electrons as described above, the functional material being a quantum dot material, that is, a particle size having a monodisperse size distribution, a shape thereof It can be selected from different nanotopography such as spheres, cubes, rods or branched structures.
- the functional material being a quantum dot material, that is, a particle size having a monodisperse size distribution, a shape thereof It can be selected from different nanotopography such as spheres, cubes, rods or branched structures.
- the composition for printing electrons is a composition for printing electrons as described above, the functional material being a luminescent quantum dot material having an emission wavelength between 380 nm and 2500 nm.
- the composition for printing electrons includes the inorganic functional material selected from the group consisting of: Group IV, II- Binary or multi-component semiconductor compounds of group VI, II-V, III-V, III-VI, IV-VI, I-III-VI, II-IV-VI, II-IV-V Any one of them, or a mixture of any two or more thereof.
- the composition for printing electrons is used in a composition for printing electrons as described above, the functional material being a perovskite nanoparticle material, preferably a luminescent perovskite nanomaterial, a metal A nanoparticle material, a metal oxide nanoparticle material, or a mixture of any two or more thereof.
- the composition for printing electrons is used in a composition for printing electrons as described above, the functional material being an organic functional material.
- the composition for printing electrons is used in a composition for printing electrons as described above, and the organic functional material may be selected from a hole injection material (HIM), a hole transport material (HTM). ), electron transport material (ETM), electron injecting material (EIM), electron blocking material (EBM), hole blocking material (HBM), illuminator (Emitter), host material (Host), and organic dye , or a mixture of any two or more thereof.
- HIM hole injection material
- HTM hole transport material
- ETM electron transport material
- EIM electron injecting material
- EBM electron blocking material
- HBM hole blocking material
- Emitter illuminator
- host material Host
- organic dye or a mixture of any two or more thereof.
- the composition for printing electrons is described above for use in a composition for printing electrons, the organic functional material comprising at least one host material and at least one illuminant.
- the composition for printing electrons described above is characterized in that the functional material accounts for 0.3% to 30% by weight of the composition for printing electrons, and the solvent system is included.
- the weight percentage of the composition for printing electrons is 70% to 99.7%.
- the present invention also provides an electronic device comprising a functional layer printed or coated by any of the compositions described above, wherein the organic solvent based on heteroaromatic and having the general formula (I) is included Evaporation from the solvent system to form a functional film.
- the electronic device described above wherein the electronic device may be selected from the group consisting of: a quantum dot light emitting diode (QLED), a quantum dot photovoltaic cell (QPV), a quantum dot light emitting cell (QLEEC), a quantum dot field effect.
- Tube QFET
- quantum dot luminescence field effect transistor quantum dot laser, quantum dot sensor
- organic light emitting diode OLED
- organic photovoltaic cell OLED
- OLED organic light emitting cell
- OFEC organic light emitting cell
- OFET organic field effect transistor
- organic Luminescent field effect transistors organic lasers, and organic sensors.
- the present invention also provides a method for preparing a film of a functional material, wherein a coating according to any of the above-described compositions is applied to a substrate by printing or coating, wherein the method of printing or coating may be selected from ( But not limited to): inkjet printing, jet printing (NozzlePrinting), typography, screen printing, dip coating, spin coating, blade coating, roller printing, torsion roll printing, lithography, flexographic printing, rotary printing , spraying, brushing, pad printing, slit type extrusion coating, etc.
- the present invention also provides a printing process for a composition for printing electrons as described above and its use in electronic devices, particularly in electroluminescent devices.
- the invention has the beneficial effects that the composition for printing electrons of the invention can adjust the viscosity and surface tension to a suitable range according to a specific printing method, especially inkjet printing, in use, so as to facilitate Print and form a film with a uniform surface.
- the organic solvent can be effectively removed by post-treatment, such as heat treatment or vacuum treatment, to ensure the performance of the electronic device.
- the present invention provides a printing ink for preparing a high quality functional film, particularly a printing ink comprising quantum dots and an organic semiconductor material, which provides an excellent technical solution for printed electronic or optoelectronic devices.
- FIG. 1 is a structural view of a preferred embodiment of a light emitting device according to the present invention, in which 101 is a substrate, 102 is an anode, 103 is a hole injection layer (HIL) or a hole transport layer (HTL), 104 is A light-emitting layer (electroluminescence device) or a light absorbing layer (photovoltaic cell), 105 is an electron injection layer (EIL) or an electron transport layer (ETL), and 106 is a cathode.
- HIL hole injection layer
- HTL hole transport layer
- 104 is A light-emitting layer (electroluminescence device) or a light absorbing layer (photovoltaic cell)
- 105 is an electron injection layer (EIL) or an electron transport layer (ETL)
- 106 is a cathode.
- the present invention provides a composition for printing electrons, and also relates to a printing process of the composition and its use in electronic devices, particularly in optoelectronic devices, especially in electroluminescent devices.
- the invention still further relates to electronic devices made using such compositions.
- composition for printing electrons of the present invention and the term printing ink, or ink, have the same meaning and are interchangeable.
- composition for printing electrons comprising at least one functional material and a solvent system comprising at least one organic solvent, the organic solvent comprising at least one heteroaromatic based And having the organic solvent of the formula (I):
- Ar 1 is a heteroaromatic ring having 5 to 10 carbon atoms, n is an integer greater than or equal to 0, and R is a substituent characterized in that the organic solvent having a heteroaromatic group and having the general formula (I) has a boiling point ⁇ 120 ° C and can be evaporated from the solvent system to form a film of functional material.
- Ar 1 is a heteroaromatic ring having 5 to 10 carbon atoms.
- a heteroaromatic group refers to a hydrocarbon group (containing a hetero atom) comprising at least one heteroaromatic ring, including a monocyclic group and a polycyclic ring system. These polycyclic rings may have two or more rings in which two carbon atoms are shared by two adjacent rings, a fused ring. At least one of these rings of the polycyclic ring is a heteroaromatic group.
- heteroaromatic group may be selected from, but not limited to, furan, benzofuran, thiophene, benzothiophene, pyrrole, pyrazole, triazole, imidazole, oxazole, oxadiazole, thiazole, tetra Azole, anthracene, oxazole, pyrroloimidazole, pyrrolopyrrole, thienopyrrole, thienothiophene, furopyrrol, furanfuran, thienofuran, benzisoxazole, benzisothiazole, benzimidazole , pyridine, pyrazine, pyridazine, pyrimidine, triazine, quinoline, isoquinoline, o-diazine, quinoxaline, Phenanthrene, benzidine, quinazoline, quinazolinone, and derivatives thereof.
- the total number of atoms other than H in all substituents R in formula (I) as described above is greater than or equal to two.
- the atoms other than H in all the substituents R described herein include atoms of C, Si, N, P, O, S, F, Cl, Br, I, etc., but are not limited thereto.
- a methoxy substituent and two chlorine substituents thereof and the like are within the scope of the present invention.
- the total number of atoms other than H in all substituents R is greater than or equal to 2, preferably from 2 to 20, more preferably from 2 to 10, most preferably from 3 to 10.
- the composition for printing electrons of the present invention comprises a heteroaromatic-based organic solvent having the general formula (I) which may have a structure represented by the following formula:
- X can be CR 1 or N
- At least one X or Y in each formula is a non-C atom (so-called hetero atom);
- the composition for printing electrons according to the present invention comprises a heteroaromatic-based organic solvent having the general formula (I), wherein Ar 1 is preferred from Any of the following structural units:
- organic solvent based on heteroaromatic and having the general formula (I) for dissolving functional materials, the boiling point parameters of which are to be taken into consideration when selecting.
- the organic solvent based on heteroaromatic and having the general formula (I) has a boiling point > 150 °C.
- the organic solvent based on heteroaromatic and having the general formula (I) has a boiling point of ⁇ 180 ° C; In some embodiments, the organic solvent based on heteroaromatic and having the general formula (I) has a boiling point ⁇ 200 ° C; in certain embodiments, the organic solvent based on heteroaromatic and having the general formula (I) Its boiling point is ⁇ 250 ° C; in other preferred embodiments, the organic solvent based on heteroaromatic and having the general formula (I) has a boiling point of ⁇ 275 ° C or ⁇ 300 ° C. The boiling points within these ranges are beneficial for preventing nozzle clogging of the inkjet printhead.
- the organic solvent based on heteroaromatic and having the general formula (I) can be evaporated from a solvent system to form a film comprising a functional material.
- the composition for printing electrons according to the invention comprises a heteroaromatically based heteroaromatic compound having the general formula (I) and having an organic solvent of the formula (I)
- the surface tension at 25 ° C is in the range of 19 dyne / cm to 50 dyne / cm.
- an organic solvent based on heteroaromatics and having the general formula (I) for dissolving functional materials the surface tension parameters of which are to be taken into consideration when selecting. Suitable ink surface tension parameters are suitable for a particular substrate and a particular printing method.
- the heteroaromatic based organic solvent of formula (I) has a surface tension at 25 ° C in the range of from about 19 dyne / cm to 50 dyne / cm;
- the organic solvent based on heteroaromatic and having the general formula (I) has a surface tension at 25 ° C in the range of from about 22 dyne / cm to 35 dyne / cm;
- the organic solvent based on heteroaromatic and having the general formula (I) has a surface tension at 25 ° C in the range of from about 25 dyne/cm to 33 dyne/cm.
- the ink of the present invention has a surface tension at 25 ° C in the range of about 19 dyne / cm to 50 dyne / cm; more preferably in the range of 22 dyne / cm to 35 dyne / cm; It is preferably in the range of 25 dyne/cm to 33 dyne/cm.
- a composition according to the present invention wherein the organic solvent based on heteroaromatic and having the general formula (I) has a viscosity at 25 ° C in the range of 1 cPs to 100 cPs.
- the viscosity parameter of the ink is taken into consideration when selecting.
- the viscosity can be adjusted by different methods, such as by the selection of a suitable organic solvent and the concentration/weight ratio of the functional material in the ink.
- the content of the solvent system of the present invention containing a heteroaromatic based organic solvent having the general formula (I) in the printing ink can be conveniently adjusted to an appropriate range in accordance with the printing method used.
- the composition for printing electrons according to the present invention comprises a functional material in a weight ratio of 0.3% to 30% by weight, more preferably 0.5% by weight of the composition for printing electrons.
- the organic solvent based on heteroaromatic and having the general formula (I) has a viscosity of less than 100 cps; in a more preferred embodiment, the heteroaromatic based and general formula The organic solvent of (I) has a viscosity of less than 50 cps; in a most preferred embodiment, the heteroaromatic based organic solvent of the formula (I) has a viscosity of from 1.5 to 20 cps.
- the viscosity herein refers to the viscosity at ambient temperature at the time of printing, and is generally 15 to 30 ° C, more preferably 18 to 28 ° C, still more preferably 20 to 25 ° C, and most preferably 23 to 25 ° C.
- Compositions so formulated will be particularly suitable for ink jet printing.
- the composition for printing electrons of the present invention has a viscosity at 25 ° C of about 1 cps to 100 cps when it is formulated according to the above ratio; more preferably at 1 cps. Up to the range of 50 cps; most preferably in the range of 1.5 cps to 20 cps.
- the resulting ink is capable of forming a thin film of functional material having uniform thickness and compositional properties.
- heteroaromatic-based organic solvent of the formula (I) are, but not limited to, 2-phenylpyridine, 3-phenylpyridine, 4-(3-phenylpropyl)pyridine , quinoline, isoquinoline, methyl 2-furancarboxylate, ethyl 2-furancarboxylate, and the like.
- the printing inks of the present invention comprise a single heteroaromatic based organic solvent of formula (I), preferably quinoline or isoquinoline.
- the printing inks of the present invention comprise a mixture of two or more heteroaromatic based organic solvents of formula (I).
- the printing ink of the present invention comprises an organic solvent which is a mixture of quinoline and isoquinoline.
- the printing inks of the present invention comprise an organic solvent based on heteroaromatic and having the general formula (I) and at least one other solvent, and are heteroaromatic based and have a general formula
- the organic solvent of (I) accounts for 50% or more of the total weight of the mixed solvent.
- the organic solvent represented by the general formula (I) is at least 70% by weight based on the total weight of the solvent; more preferably, the organic solvent based on heteroaromatic and having the general formula (I) accounts for at least 80% by weight based on the total weight of the mixed solvent. %.
- the organic solvent based on heteroaromatic and having the general formula (I) comprises at least 90% by weight based on the total weight of the mixed solvent, or the mixed solvent consists essentially of an organic solvent based on heteroaromatic and having the general formula (I), Or consists entirely of an organic solvent based on heteroaromatics and having the general formula (I).
- another organic solvent as described above is selected from the group consisting of an optionally substituted or unsubstituted aromatic solvent.
- the printing inks of the present invention comprise an organic solvent which is a mixture of quinoline and dodecylbenzene.
- the printing inks of the present invention comprise an organic solvent which is a mixture of isoquinoline and dodecylbenzene.
- the printing inks of the present invention comprise an organic solvent which is a mixture of quinoline and 3-phenoxytoluene.
- the printing inks of the present invention comprise an organic solvent which is a mixture of isoquinoline and 3-phenoxytoluene.
- examples of another organic solvent as described above include, but are not limited to, methanol, ethanol, 2-methoxyethanol, dichloromethane, chloroform, chlorobenzene, o-di Chlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4 dioxane, acetone, methyl ethyl ketone, 1,2 dichloroethane Alkane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethyl Acetamide, dimethyl sulfoxide, tetrahydronaphthalene, decalin, hydrazine, or a mixture of any two or more thereof.
- the heteroaromatic-based solvent system of the present invention is capable of effectively dissolving functional materials, that is, a solvent for replacing a conventionally used dissolving functional material as a new solvent, such as toluene, xylene, chloroform, chlorobenzene, dichlorobenzene, positive Heptane and the like.
- the printing ink may further comprise one or more components, such as surface active compounds, lubricants, wetting agents, dispersing agents, hydrophobic agents, adhesives, etc., for adjusting viscosity, film forming properties, and improving adhesion. Wait.
- components such as surface active compounds, lubricants, wetting agents, dispersing agents, hydrophobic agents, adhesives, etc., for adjusting viscosity, film forming properties, and improving adhesion. Wait.
- the printing ink can be deposited to obtain a functional film by a variety of printing or coating techniques including, but not limited to, ink jet printing, inkjet printing, letterpress printing, screen printing, dip coating. , spin coating, blade coating, roller printing, torsion roller printing, lithography, flexographic printing, rotary printing, spraying, brushing, pad printing, slit-type extrusion coating, and the like.
- Preferred printing techniques are ink jet printing, jet printing and gravure printing.
- HelmutKipphan's Printing Media Handbook: Techniques and Production Methods" (Hand book of Print Media: Technologies and Production Methods).
- printing inks suitable for inkjet printing require adjustment of the surface tension, viscosity, and wettability of the ink so that the ink can be ejected through the nozzle at a printing temperature (such as room temperature, 25 ° C) without being sprayed. Drying on the nozzle or clogging the nozzle, or forming a continuous, flat and defect-free film on a particular substrate.
- composition for printing electrons of the present invention comprises at least one functional material.
- the functional material preferably refers to a material having certain photoelectric functions.
- Photoelectric functions include, but are not limited to, hole injection function, hole transport function, electron transport function, electron injection function, electron blocking function, hole blocking function, light emitting function, main body function, and light absorbing function.
- the corresponding functional materials are called hole injection material (HIM), hole transport material (HTM), electron transport material (ETM), electron injecting material (EIM), electron blocking material (EBM), hole blocking material (HBM). ), Emitter, Host and organic dyes.
- the functional material may be an organic material or an inorganic material.
- the composition for printing electrons of the present invention comprises at least one functional material that is an inorganic nanomaterial.
- the inorganic nano material is an inorganic semiconductor nanoparticle material.
- the inorganic nanomaterial has an average particle diameter in the range of about 1 to 1000 nm. In certain preferred embodiments, the inorganic nanomaterials have an average particle size of from about 1 to 100 nm. In certain more preferred embodiments, the inorganic nanomaterials have an average particle size of from about 1 to 20 nm, most preferably from 1 to 10 nm.
- the inorganic nanomaterials may be selected from different shapes including, but not limited to, different nanotopography such as spheres, cubes, rods, discs, or branched structures, as well as mixtures of particles of various shapes.
- the inorganic nanomaterial is a quantum dot material having a very narrow, monodisperse size distribution, i.e., the size difference between the particles and the particles is very small.
- the deviation of the monodisperse quantum dots in size is less than 15% rms; more preferably, the deviation of the monodisperse quantum dots in size is less than 10% rms; most preferably, monodisperse Quantum dots have a root mean square deviation of less than 5% rms in size.
- the inorganic nanomaterial is a luminescent material.
- the luminescent inorganic nanomaterial is a quantum dot luminescent material.
- luminescent quantum dots can illuminate at wavelengths between 380 nanometers and 2500 nanometers.
- quantum dots having a CdS core have an emission wavelength in the range of about 400 nm to 560 nm; quantum dots having a CdSe core have an emission wavelength in the range of about 490 nm to 620 nm; and a quantum having a CdTe core
- the illuminating wavelength of the dot is in the range of about 620 nm to 680 nm;
- the luminescent wavelength of the quantum dot having the InGaP nucleus is in the range of about 600 nm to 700 nm;
- the luminescent wavelength of the quantum dot having the PbS nucleus is about 800 nm to 2500 In the range of nanometers;
- the wavelength of the quantum dots having the PbSe core is in the range of about 1200 nm to 2500 nm;
- the wavelength of the quantum dots having the CuInGaS core is in the range
- the quantum dot material comprises at least one material capable of emitting blue light having an emission peak wavelength of 450 nm to 460 nm, a green light having an emission peak wavelength of 520 nm to 540 nm, and an emission peak wavelength of 615 nm.
- the quantum dots contained may be selected from a particular chemical composition, topographical structure, and/or size to achieve light that emits the desired wavelength under electrical stimulation.
- the narrow particle size distribution of quantum dots enables quantum dots to have a narrower luminescence spectrum. Furthermore, depending on the chemical composition and structure employed, the size of the quantum dots needs to be adjusted accordingly within the above-described size range to achieve the luminescent properties of the desired wavelength.
- the luminescent quantum dots are semiconductor nanocrystals.
- semiconductor nanocrystals range in size from about 2 nanometers to about 15 nanometers.
- the size of the quantum dots needs to be adjusted accordingly within the above-described size range to achieve the luminescent properties of the desired wavelength.
- the semiconductor nanocrystal comprises at least one semiconductor material, wherein the semiconductor material may be selected from group IV, II-VI, II-V, III-V, III-VI, IV-VI, I of the periodic table. a binary or polyvalent semiconductor compound of Groups III-VI, II-IV-VI, II-IV-V or a mixture of any two or more thereof.
- the semiconductor material include, but are not limited to, Group IV semiconductor compounds including, for example, elemental Si, Ge, and binary compounds SiC, SiGe; Group II-VI semiconductor compounds, for example, wherein the binary compound includes CdSe, CdTe, CdO, CdS, CdSe, ZnS, ZnSe, ZnTe, ZnO, HgO, HgS, HgSe, HgTe, ternary compounds including CdSeS, CdSeTe, CdSTe, CdZnS, CdZnSe, CdZnTe, CgHgS, CdHgSe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, HgZnS, HgSeSe, and quaternary compounds include CgHgSeS, CdHgSeTe, CgHgSTe, CdZnS, H
- the luminescent quantum dots comprise a Group II-VI semiconductor material, preferably selected from the group consisting of CdSe, CdS, CdTe, ZnO, ZnSe, ZnS, ZnTe, HgS, HgSe, HgTe, CdZnSe, or any two or The above mixture.
- this material can be used as a luminescent quantum dot for visible light due to the relatively mature synthesis of CdSe, CdS.
- the luminescent quantum dots comprise a III-V semiconductor material, preferably selected from the group consisting of InAs, InP, InN, GaN, InSb, InAsP, InGaAs, GaAs, GaP, GaSb, AlP, AlN, AlAs, AlSb, CdSeTe, ZnCdSe or a mixture of any two or more thereof.
- the luminescent quantum dots comprise a Group IV-VI semiconductor material, preferably selected from the group consisting of PbSe, PbTe, PbS, PbSnTe, Tl 2 SnTe 5 or a mixture of any two or more thereof.
- the quantum dots are core-shell structures.
- the core and the shell respectively comprise one or more semiconductor materials, either identically or differently.
- the core of the quantum dot may be selected from the group IV, II-VI, II-V, III-V, III-VI, IV-VI, I-III-VI, II of the Periodic Table of the Elements above. a binary or polyvalent semiconductor compound of Group IV-VI, Group II-IV-V.
- quantum dot nuclei include, but are not limited to, ZnO, ZnS, ZnSe, ZnTe, CdO, CdS, CdSe, CdTe, MgS, MgSe, GaAs, GaN, GaP, GaSe, GaSb, HgO, HgS, HgSe, HgTe, InAs, InN, InSb, AlAs, AlN, AlP, AlSb, PbO, PbS, PbSe, PbTe, Ge, Si, or an alloy thereof or a mixture of any two or more thereof.
- the shell of the quantum dot contains a semiconductor material that is the same as or different from the core.
- Semiconductor materials that can be used for the shell include Group IV, II-VI, II-V, III-V, III-VI, IV-VI, I-III-VI, II-IV-VI of the Periodic Table of the Elements. Group, II-IV-V binary or multi-component semiconductor compounds.
- quantum dot nuclei include, but are not limited to, ZnO, ZnS, ZnSe, ZnTe, CdO, CdS, CdSe, CdTe, MgS, MgSe, GaAs, GaN, GaP, GaSe, GaSb, HgO, HgS, HgSe, HgTe, InAs, InN, InSb, AlAs, AlN, AlP, AlSb, PbO, PbS, PbSe, PbTe, Ge, Si, or an alloy thereof or a mixture of any two or more thereof.
- the shell may include a single layer or a multilayer structure.
- the shell may comprise one or more semiconductor materials that are the same or different from the core.
- the shell has a thickness of from about 1 to 20 layers. In a more preferred embodiment, the shell has a thickness of about 5 to 10 layers. In some embodiments, two or more shells are included on the surface of the quantum dot core.
- the semiconductor material used for the shell may have a larger band gap than the core.
- the shell core has a type I semiconductor heterojunction structure.
- the semiconductor material used for the shell may have a smaller band gap than the core.
- the semiconductor material used for the shell may have the same or close atomic crystal structure as the core. Such a choice is beneficial to reduce the stress between the core shells and make the quantum dots more stable.
- Examples of suitable luminescent quantum dots using a core-shell structure are:
- Red light CdSe/CdS, CdSe/CdS/ZnS, CdSe/CdZnS, etc.;
- Green light CdZnSe/CdZnS, CdSe/ZnS, etc.
- Blue light CdS/CdZnS, CdZnS/ZnS, and the like.
- a preferred method of preparing quantum dots is a colloidal growth method.
- the method of preparing monodisperse quantum dots is selected from the group consisting of hot-inject and/or heating-up.
- the preparation method is contained in the document NanoRes, 2009, 2, 425-447; Chem. Mater., 2015, 27(7), pp 2246-2285.
- the surface of the quantum dots may comprise an organic ligand.
- the organic ligand can control the growth process of the quantum dots, regulate the morphology of the quantum dots and reduce the surface defects of the quantum dots, thereby improving the luminous efficiency and stability of the quantum dots.
- the organic ligand may be selected from, but not limited to, pyridine, pyrimidine, furan, amine, alkylphosphine, alkylphosphine oxide, alkylphosphonic acid or alkylphosphinic acid, alkyl mercaptan, and the like.
- organic ligands include, but are not limited to, tri-n-octylphosphine, tri-n-octylphosphine oxide, trihydroxypropylphosphine, tributylphosphine, tris(dodecyl)phosphine, dibutyl phosphite , tributyl phosphite, octadecyl phosphite, trilauryl phosphite, tris(dodecyl) phosphite, triisodecyl phosphite, bis(2-ethylhexyl) phosphate, Tris(tridecyl)phosphate, hexadecylamine, oleylamine, octadecylamine, bisoctadecylamine, octadecylamine, bis(2-ethylhexyl)amine, oleyl
- the surface of the quantum dots may comprise an inorganic ligand.
- Quantum dots protected by inorganic ligands can be obtained by ligand exchange of organic ligands on the surface of quantum dots. Examples of specific inorganic ligands include, but are not limited to, S 2- , HS - , Se 2- , HSe - , Te 2- , HTe - , TeS 3 2- , OH - , NH 2 - , PO 4 3- , MoO 4 2, etc.
- the quantum dot surface can have one or more of the same or different ligands.
- the luminescence spectrum exhibited by the monodisperse quantum dots may have a symmetrical peak shape and a narrow half width.
- the quantum dot has a half-width of light emission of less than 70 nanometers; more preferably, the quantum half-width of the quantum dot is less than 40 nanometers; most preferably, the quantum dot has a half-width of light emission of less than 30 nanometers.
- the quantum dots have a luminescence quantum efficiency of greater than 10%, more preferably greater than 50%, more preferably greater than 60%, and most preferably greater than 70%.
- the luminescent semiconductor nanocrystals are nanorods.
- the properties of nanorods are different from those of spherical nanocrystals.
- the luminescence of the nanorods is polarized along the long rod axis, while the luminescence of the spherical grains is unpolarized.
- Nanorods have excellent optical gain characteristics, making them possible to use as laser gain materials.
- the luminescence of the nanorods can be reversibly turned on and off under the control of an external electric field. These characteristics of the nanorods may be preferably incorporated into the device of the present invention under certain circumstances.
- the inorganic nanomaterial is a perovskite nanoparticle material, particularly a luminescent perovskite nanoparticle material.
- the perovskite nanoparticle material may have the structural formula of AMX 3 wherein A may be selected from an organic amine or an alkali metal cation, M may be selected from a metal cation, and X may be selected from an oxygen or a halogen anion.
- CsPbCl 3 CsPb (Cl/Br) 3 , CsPbBr 3 , CsPb (I/Br) 3 , CsPbI 3 , CH 3 NH 3 PbCl 3 , CH 3 NH 3 Pb (Cl/Br 3 , CH 3 NH 3 PbBr 3 , CH 3 NH 3 Pb(I/Br) 3 , CH 3 NH 3 PbI 3 and the like.
- the inorganic nanomaterial is a metal nanoparticle material, preferably a luminescent metal nanoparticle material.
- the metal nanoparticles include, but are not limited to, chromium (Cr), molybdenum (Mo), tungsten (W), ruthenium (Ru), rhenium (Rh), nickel (Ni), silver (Ag), copper (Cu). Nanoparticles of metals such as zinc (Zn), palladium (Pd), gold (Au), hungry (Os), ruthenium (Re), iridium (Ir), and platinum (Pt).
- the inorganic nanomaterial has charge transport properties.
- the inorganic nanomaterial has electron transport capabilities.
- such inorganic nanomaterials are selected from the group consisting of n-type semiconductor materials.
- the n-type inorganic semiconductor material may include, but are not limited to, a metal chalcogen compound compound, a metal phosphorus group element compound, or an elemental semiconductor such as a metal oxide, a metal sulfide, a metal selenide, a metal telluride, a metal nitride. , metal phosphide, or metal arsenide.
- Preferred n-type inorganic semiconductor materials may be selected from, but not limited to, ZnO, ZnS, ZnSe, TiO 2 , ZnTe, GaN, GaP, AlN, CdSe, CdS, CdTe, CdZnSe or a mixture of any two or more thereof.
- the inorganic nanomaterial has a hole transporting ability.
- such inorganic nanomaterials may be selected from p-type semiconductor materials.
- the inorganic p-type semiconductor material may be selected from NiOx, WOx, MoOx, RuOx, VOx, CuOx or a mixture of any two or more thereof.
- the printing ink of the present invention may comprise at least two and two or more inorganic nanomaterials.
- composition for printing electrons of the present invention may comprise at least one organic functional material.
- the organic functional material may include, but is not limited to, holes (also called holes) injection or transport materials (HIM/HTM), hole blocking materials (HBM), electron injection or transport materials (EIM/ETM), electrons.
- Barrier material EBM
- organic host material Host
- singlet illuminant fluorescent illuminant
- thermally activated delayed fluorescent luminescent material TADF
- triplet illuminant phosphorescent illuminant
- the solubility of the organic functional material in the heteroaromatic solvent of the present invention may be at least 0.2 wt%, more preferably at least 0.3 wt%, more preferably at least 0.6 wt%, still more preferably at least 1.0 wt%, most preferably at least 1.5 wt%.
- the organic functional material may be a small molecule and a high polymer material.
- the small molecule organic material means a material having a molecular weight of at most 4000 g/mol, and the material having a molecular weight higher than 4000 g/mol is collectively referred to as a high polymer.
- the composition for printing electrons of the present invention comprises a functional material that is an organic small molecule material.
- the composition for printing electrons of the present invention wherein the organic functional material may comprise at least one host material and at least one illuminant.
- the organic functional material may comprise a host material and a singlet emitter.
- the organic functional material may comprise a host material and a triplet state Light body.
- the organic functional material may comprise a host material and a thermally activated delayed fluorescent luminescent material.
- the organic functional material may comprise a hole transporting material (HTM), and more preferably, the HTM comprises a crosslinkable group.
- HTM hole transporting material
- organic small molecule functional materials suitable for the preferred embodiment will be described in some detail below (but are not limited thereto).
- Suitable organic HIM/HTM materials may optionally comprise compounds having the following structural units: phthalocyanine, porphyrin, amine, aromatic amine, biphenyl triarylamine, thiophene, thiophene such as dithienothiophene and thiophene, pyrrole , aniline, carbazole, azide and azepine and its derivatives, but are not limited thereto.
- suitable HIMs also include fluorocarbon-containing polymers, conductively doped polymers, conductive polymers such as PEDOT:PSS, but are not limited thereto.
- An electron blocking layer is used to block electrons from adjacent functional layers, particularly the luminescent layer.
- the presence of an EBL generally results in an increase in luminous efficiency.
- the electron blocking material (EBM) of the electron blocking layer (EBL) requires a higher LUMO than an adjacent functional layer such as a light emitting layer.
- the HBM has a larger excited state level than the adjacent luminescent layer, such as a singlet or triplet, depending on the illuminant, while the EBM has a hole transport function.
- HIM/HTM materials that typically have high LUMO levels can be used as EBMs.
- cyclic aromatic amine-derived compounds useful as HIM, HTM or EBM include, but are not limited to, the following general structures:
- Each of Ar 1 to Ar 9 may be independently selected from the group consisting of a cyclic aromatic hydrocarbon compound such as benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene, phenalrene, phenanthrene, anthracene, anthracene, fluorene, anthracene, anthracene; Heterocyclic compounds such as dibenzothiophene, dibenzofuran, furan, thiophene, benzofuran, benzothiophene, oxazole, pyrazole, imidazole, triazole, isoxazole, thiazole, oxadiazole, evil Triazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, acesulfazine, oxadiazine, hydrazine
- each of Ar may be further substituted, and the substituent may be selected from, but not limited to, hydrogen, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl or heteroaryl.
- Ar 1 to Ar 9 may be independently selected from the group consisting of the following, but are not limited thereto:
- n is an integer from 1 to 20; X 1 to X 8 are CH or N; and Ar 1 is as defined above.
- metal complexes that can be used as HTM or HIM include, but are not limited to, the following general structures:
- M is a metal having an atomic weight greater than 40
- (Y 1 -Y 2 ) is a bidentate ligand, Y 1 and Y 2 are independently selected from C, N, O, P and S; L is an ancillary ligand; m is an integer selected from 1 to this metal The maximum coordination number; m+n is the maximum coordination number of this metal.
- (Y 1 -Y 2 ) is a 2-phenylpyridine derivative.
- (Y 1 -Y 2 ) is a carbene ligand.
- M can be selected from the group consisting of Ir, Pt, Os, and Zn.
- the HOMO of the metal complex is greater than -5.5 eV (relative to the vacuum level).
- HIM/HTM compounds are listed in the table below, but are not limited thereto:
- the example of the triplet host material is not particularly limited, and any metal complex or organic compound may be used as a host as long as its triplet energy is higher than that of the illuminant, particularly the triplet illuminant or the phosphorescent illuminant.
- metal complexes that can be used as the triplet host include, but are not limited to, the following general structure:
- M is a metal
- (Y 3 -Y 4 ) is a bidentate ligand, Y 3 and Y 4 are independently selected from C, N, O, P, and S
- L is an ancillary ligand
- m is an integer, the value thereof The maximum coordination number selected from 1 to this metal
- m+n is the maximum coordination number of this metal.
- the metal complex that can be used as the triplet host can have one of the following forms:
- (O-N) is a two-dentate ligand in which the metal is coordinated to the O and N atoms.
- M is selectable from Ir and Pt.
- Examples of the organic compound which can be a host of a triplet state may be selected from, but not limited to, a compound containing a cyclic aromatic hydrocarbon group such as benzene, biphenyl, triphenyl, benzo, anthracene; a compound containing an aromatic heterocyclic group, Such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, carbazole, pyridinium, pyrrole dipyridine, Pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxazine , o
- each Ar may be further substituted, and the substituent may be hydrogen, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl or heteroaryl, but is not limited thereto.
- the triplet host material can be selected from compounds containing at least one of the following groups, but is not limited thereto:
- the R 1 -R 7 may be independently of one another selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl and heteroaryl, but not limited thereto, when they are an aryl group or a heteroaryl group, which is the same meaning as above 2 Ar 1 and Ar; n is an integer from 0 to 20; X 1 -X 8 is selected in CH or N; X 9 is selected from At CR 1 R 2 or NR 1 .
- triplet host materials examples include but are not limited to this:
- the example of the singlet host material is not particularly limited, and any organic compound may be used as a host as long as its singlet energy is higher than that of the illuminant, particularly the singlet illuminant or the luminescent illuminant.
- Examples of the organic compound used as the singlet host material may be selected from, but not limited to, a cyclic aromatic compound such as benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene, anthracene, phenanthrene, anthracene, anthracene.
- a cyclic aromatic compound such as benzene, biphenyl, triphenyl, benzo, naphthalene, anthracene, anthracene, phenanthrene, anthracene, anthracene.
- aromatic heterocyclic compounds such as dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, oxime Carbazole, pyridinium, pyrrole dipyridine, pyrazole, imidazole, triazole, isoxazole, thiazole, oxadiazole, oxatriazole, dioxazole, thiadiazole, pyridine, pyridazine, pyrimidine, Pyrazine, triazine, oxazine, oxazine, oxadiazine, hydrazine, benzimidazole, oxazole, pyridazine, benzoxazole, benzoisoxazole, benzothiazole, quinoline, isoquine Porphy
- the singlet host material may be selected from, but not limited to, a compound comprising at least one of the following groups:
- R 1 may be independently selected from the group consisting of hydrogen, alkyl, alkoxy, amino, alkene, alkyne, aralkyl, heteroalkyl, aryl and heteroaryl;
- Ar 1 is aryl or a heteroaryl group, but is not limited thereto, which has the same meaning as Ar 1 defined in the above HTM;
- n is an integer from 0 to 20;
- X 1 -X 8 is selected from CH or N;
- X 9 and X 10 are selected from CR 1 R 2 or NR 1 .
- Singlet emitters tend to have longer conjugated pi-electron systems. To date, there have been many examples such as styrylamine and its derivatives and indenoindene and its derivatives.
- the singlet emitter may be selected from the group consisting of monobasic styrylamine, dibasic styrylamine, ternary styrylamine, quaternary styrylamine, styrene phosphine, styrene ether and arylamine, But it is not limited to this.
- the monostyrylamine refers to a compound comprising an unsubstituted or optionally substituted styrene group and at least one amine, preferably an aromatic amine.
- the dibasic styrylamine refers to a compound comprising two unsubstituted or optionally substituted styrene groups and at least one amine, preferably an aromatic amine.
- the ternary styrylamine refers to a compound comprising three unsubstituted or optionally substituted styrene groups and at least one amine, preferably an aromatic amine.
- Tetrastyrylamine refers to a compound comprising four unsubstituted or optionally substituted styrene groups and at least one amine, preferably an aromatic amine.
- the preferred styrene is stilbene, which may be further substituted. Accordingly, the definitions of phosphines and ethers are similar to those of amines.
- An arylamine or an aromatic amine refers to a compound comprising three unsubstituted or optionally substituted aromatic ring or heterocyclic systems directly bonded to a nitrogen. At least one of these aromatic or heterocyclic ring systems is preferably selected from the fused ring system, and most preferably has at least 14 aromatic ring atoms.
- Aromatic decylamine refers to a compound in which one of the diarylamine groups is attached directly to the oxime, preferably at the position of 9.
- Aromatic quinone diamine refers to a compound in which two diarylamine groups are attached directly to the oxime, preferably at the 9,10 position.
- the aromatic decylamine, the aromatic guanidine diamine, the aromatic thiamine and the aromatic thiamine are similarly defined, wherein the diarylamine group is preferably attached to the 1 or 1,6 position of the oxime.
- Further preferred singlet emitters may be selected from the group consisting of indeno-amine and indeno-diamine, benzindole-amine and benzoindole-diamine, dibenzoindenoquinone-amine And dibenzoindenoindole-diamine and the like.
- polycyclic aromatic hydrocarbon compounds in particular derivatives of the following compounds: for example, 9,10-bis(2-naphthoquinone), naphthalene, tetraphenyl, xanthene, phenanthrene , ⁇ (such as 2,5,8,11-tetra-t-butyl fluorene), anthracene, phenylene such as (4,4'-bis(9-ethyl-3-carbazolevinyl)-1 , 1'-biphenyl), di-indeno pyrene, chrysene, decacyclene, coronene, fluorene, spirobifluorene, pyrene aryl group, arylene group ethylene, cyclopentadiene such as tetraphenyl cyclopentadiene, Rubrene, coumarin, rhodamine, quinacridone, pyran such as 4
- TDF Thermally activated delayed fluorescent luminescent material
- the thermally activated delayed fluorescent luminescent material is a third generation organic luminescent material developed after organic fluorescent materials and organic phosphorescent materials.
- Such materials generally have a small singlet-triplet energy level difference ( ⁇ E st ), and triplet excitons can be converted into singlet exciton luminescence by inter-system crossing. This can make full use of the singlet excitons and triplet excitons formed under electrical excitation.
- the quantum efficiency in the device can reach 100%.
- the TADF material needs to have a small singlet-triplet energy level difference, typically ⁇ E st ⁇ 0.3eV, more preferably ⁇ E st ⁇ 0.2eV, more preferably ⁇ E st ⁇ 0.1eV, and most preferably ⁇ E st ⁇ 0.05eV.
- TADF has a more preferred fluorescence quantum efficiency.
- TADF luminescent materials are listed in the table below, but are not limited to this:
- Triplet emitters are also known as phosphorescent emitters.
- the triplet emitter is a metal complex of the formula M(L) n , wherein M is a metal atom, and each occurrence of L may be the same or different, which is an organic ligand Connected to the metal atom M by one or more position linkages or coordination, n is an integer greater than 1, more preferably 1, 2, 3, 4, 5 or 6.
- these metal complexes are coupled to one polymer by one or more positions, most preferably by an organic ligand.
- the metal atom M may be selected from transition metal elements or lanthanides or actinides, etc., preferably Ir, Pt, Pd, Au, Rh, Ru, Os, Sm, Eu, Gd, Tb, Dy, Re, Cu or Ag is particularly preferably Os, Ir, Ru, Rh, Re, Pd or Pt, but is not limited thereto.
- the triplet emitter may comprise a chelating ligand, ie a ligand, coordinated to the metal by at least two bonding sites, it being particularly preferred to consider that the triplet emitter comprises two or three identical or different Double or multidentate ligand.
- Chelating ligands are beneficial for increasing the stability of metal complexes.
- organic ligand examples may be selected from, but not limited to, a phenylpyridine derivative, a 7,8-benzoquinoline derivative, a 2(2-thienyl)pyridine derivative, and a 2(1-naphthyl)pyridine derivative. Or a 2 phenylquinoline derivative. All of these organic ligands may be substituted, for example by fluorine or trifluoromethyl.
- the ancillary ligand may preferably be selected from the group consisting of acetone acetate or picric acid.
- the metal complex that can be used as the triplet emitter has the following form:
- M is a metal selected from the group consisting of transition metal elements or lanthanides or actinides;
- Ar 1 may be the same or different at each occurrence, which is a cyclic group containing at least one donor atom, that is, an atom having a lone pair of electrons, such as nitrogen or phosphorus, coordinated to the metal through its cyclic group Connection;
- Ar 2 may be the same or different each time it appears, which is a cyclic group containing at least one C atom through which a cyclic group is attached to the metal;
- Ar 1 and Ar 2 are bonded by a covalent bond Together, each may carry one or more substituent groups, or may be further joined together by a substituent group;
- each occurrence of L may be the same or different, which is an auxiliary ligand, preferably a bidentate chelate ligand, Most preferred is a monoanionic bidentate chelating ligand;
- m is 1, 2 or 3, preferably 2 or 3, particularly preferably 3;
- n is 0, 1, or 2, preferably 0 or 1, in particular Preferably 0;
- triplet emitters Some examples of suitable triplet emitters are listed in the table below, but are not limited to this:
- the functional material for printing electronic compositions of the present invention may comprise a polymeric material.
- the above organic small molecule functional materials may include HIM, HTM, ETM, EIM, Host, fluorescent illuminants, phosphorescent emitters, TADF, etc., and all of them may be included as a repeating unit in a high polymer.
- the high polymer suitable for the present invention may be a conjugated high polymer.
- conjugated polymers have the following general formula:
- A can independently select the same or different structural units when appearing multiple times
- B ⁇ -conjugated structural unit having a larger energy gap, also called a backbone unit (Backbone Unit), selected from single or multiple rings
- Backbone Unit backbone Unit
- preferred unit form is benzene, biphenylene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene, 9,10-dihydrophenanthrene, anthracene, diterpene, spirobifluorene, pair Phenylacetylene, ruthenium and oxime, cis hydrazine, dibenzo-indole fluorene, anthracene naphthalene and its derivatives.
- a ⁇ -conjugated structural unit having a smaller energy gap may be selected from, but not limited to, a hole injection or transport material (HIM/) as described above.
- HTM hole injection or transport material
- EIM/ETM electron injecting or transporting material
- host material Host
- singlet illuminant fluorescent illuminant
- structural unit of heavy illuminant phosphorescent illuminant
- the functional composition for printing electronic compositions of the present invention comprises a polymeric HTM.
- the high polymer HTM material is a homopolymer, and the preferred homopolymer is selected from the group consisting of polythiophene, polypyrrole, polyaniline, polybiphenyl triarylamine, polyvinyl carbazole and derivatives thereof. .
- the high polymer HTM material is a conjugated copolymer represented by Chemical Formula 1, wherein
- A a functional group having a hole transporting ability, which may be the same or differently selected from the structural unit containing the hole injection or transport material (HIM/HTM) described above; in a preferred embodiment, A is selected From amines, biphenyls, triarylamines, thiophenes, and thiophenes such as dithienothiophenes and thiophenes, pyrrole, aniline, carbazole, indenocarbazole, indolocarbazide, pentacene, phthalocyanine, porphyrin and derivatives thereof .
- HIM/HTM hole injection or transport material
- R is each independently selected from the group consisting of hydrogen, a linear alkyl group having 1 to 20 C atoms, an alkoxy group or a thioalkoxy group, and a branched or cyclic alkane having 3 to 20 C atoms.
- a base alkoxy or thioalkoxy group or a silyl group, a substituted keto group of 1 to 20 C atoms, an alkoxycarbonyl group of 2 to 20 C atoms, 7
- r 0, 1, 2, 3 or 4;
- s 0, 1, 2, 3, 4 or 5;
- Another preferred class of organic functional materials can be polymers having electron transport capabilities, including conjugated high polymers and non-conjugated high polymers.
- Preferred high polymer ETM materials may be homopolymers, and preferred homopolymers are selected from the group consisting of polyphenanthrene, polyphenanthroline, polyfluorene, polyspiroquinone, polyfluorene and derivatives thereof.
- a preferred high polymer ETM material may be a conjugated copolymer represented by Chemical Formula 1, wherein A may independently select the same or different forms in multiple occurrences:
- A a functional group having an electron transporting ability, preferably selected from the group consisting of tris(8-hydroxyquinoline)aluminum (AlQ3), benzene, diphenylene, naphthalene, anthracene, phenanthrene, dihydrophenanthrene, anthracene, diterpene, Spirobiindole, p-phenylacetylene, anthracene, anthracene, 9,10-dihydrophenanthrene, phenazine, phenanthroline, ruthenium, fluorene, dibenzo-indole, anthracene, naphthalene, benzo Bismuth and its derivatives
- the composition for printing electrons of the present invention comprises a functional material that is a luminescent polymer.
- the luminescent polymer is a conjugated high polymer having the following general formula:
- A1 a functional group having a hole or electron transporting ability, which may be selected from, but not limited to, inclusion of the above hole injection or Transmission material (HIM/HTM), or structural unit of electron injection or transport material (EIM/ETM).
- HIM/HTM hole injection or Transmission material
- EIM/ETM structural unit of electron injection or transport material
- A2 a group having a light-emitting function, which may be selected from, but not limited to, a structural unit containing the above-described singlet light emitter (fluorescent light-emitting body) and heavy light-emitting body (phosphorescent light-emitting body).
- a high polymer suitable for the present invention may be a non-conjugated high polymer.
- This can be that all functional groups are on the side chain and the backbone is a non-conjugated high polymer. Examples thereof may be selected from, but not limited to, such non-conjugated high polymers used as phosphorescent host or phosphorescent materials, and such non-conjugated high polymers used as fluorescent materials.
- the non-conjugated high polymer may also be a high polymer in which functional units conjugated in the main chain are linked by a non-conjugated linking unit.
- the present invention also relates to a method of preparing a film comprising a functional material by a method of printing or coating, wherein any one of the compositions described above is applied to a substrate by printing or coating, wherein printing or coating
- the cloth method can be selected from, but not limited to, inkjet printing, jet printing (Nozzle Printing), typography, screen printing, dip coating, spin coating, blade coating, roller printing, torsion roller printing, lithography, Flexographic printing, rotary printing, spraying, brushing, pad printing, slit-type extrusion coating, etc.
- the film comprising the functional material is prepared by a method of ink jet printing.
- Inkjet printers that can be used to print the inks of the present invention are commercially available printers and include drop-on-demand printheads. These printers are available, for example, from Fujifilm Dimatix (Lebanon, NH), Trident International (Brookfield, Conn.), Epson (Torrance, Calif), Hitachi Data Systems Corporation (Santa Clara, Calif), Xaar PLC (Cambridge, United Kingdom), and Idanit Technologies, Limited (Rishon LeZion, Isreal). Purchased.
- the present invention can be printed using Dimatix Materials Printer DMP-3000 (Fujifilm).
- the invention further relates to an electronic device comprising one or more functional films, wherein at least one functional film is prepared using the printing ink composition of the invention, in particular by printing or coating Prepared.
- Suitable electronic devices include, but are not limited to, quantum dot light emitting diodes (QLEDs), quantum dot photovoltaic cells (QPVs), quantum dot luminescent cells (QLEEC), quantum dot field effect transistors (QFETs), quantum dot luminescence field effect transistors, quantum dots.
- QLEDs quantum dot light emitting diodes
- QPVs quantum dot photovoltaic cells
- QLEEC quantum dot luminescent cells
- QFETs quantum dot field effect transistors
- Quant dot luminescence field effect transistors quantum dots.
- the electronic device described above is an electroluminescent device or a photovoltaic cell, as shown in FIG. 1, comprising a substrate (101), an anode (102), at least one luminescent layer or a light absorbing layer (104). ), cathode (106).
- an electroluminescent device will be described as an example.
- the substrate (101) may be opaque or transparent. Transparent substrates can be used to make transparent light-emitting components.
- the substrate can be rigid or elastic.
- the substrate can be plastic, metal, semiconductor wafer or glass. Most preferably, the substrate has a smooth surface. Substrates without surface defects are a particularly desirable choice.
- the substrate may be selected from polymeric films or plastics having a glass transition temperature Tg of 150 ° C or higher, more preferably more than 200 ° C, more preferably more than 250 ° C, and most preferably more than 300 ° C. Examples of suitable substrates are poly(ethylene terephthalate) (PET) and polyethylene glycol (2,6-naphthalene) (PEN), but are not limited thereto.
- the anode (102) may comprise a conductive metal or metal oxide, or a conductive polymer.
- the anode can easily inject holes into the HIL or HTL or the luminescent layer.
- the absolute value of the difference between the work function of the anode and the HOMO level or valence band level of the p-type semiconductor material as the HIL or HTL is less than 0.5 eV, more preferably less than 0.3 eV, and most preferably less than 0.2eV.
- the anode material include, but are not limited to, Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO, aluminum-doped zinc oxide (AZO), and the like.
- anode material can be deposited using any suitable technique, such as a suitable physical vapor deposition process, including RF magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.
- a suitable physical vapor deposition process including RF magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.
- the anode is patterned.
- Patterned ITO conductive substrates are commercially available and can be used to prepare devices in accordance with the present invention.
- the cathode (106) can comprise a conductive metal or metal oxide.
- the cathode can easily inject electrons into the EIL or ETL or directly into the luminescent layer.
- the absolute value of the difference between the work function of the cathode and the LUMO level or conduction band level of the n-type semiconductor material as EIL or ETL or HBL is less than 0.5 eV, more preferably less than 0.3 eV, most preferably It is less than 0.2eV.
- all materials which can be used as cathodes for OLEDs are possible as cathode materials for the devices of the invention.
- cathode material examples include, but are not limited to, Al, Au, Ag, Ca, Ba, Mg, LiF/Al, MgAg alloy, BaF2/Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, ITO, and the like.
- the cathode material can be deposited using any suitable technique, such as a suitable physical vapor deposition process, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), and the like.
- the luminescent layer (104) may include at least one layer of luminescent functional material having a thickness between 2 nm and 200 nm.
- the light-emitting layer is prepared by printing the printing ink of the present invention, wherein the printing ink comprises at least one light-emitting functional material as described above, in particular Quantum dots or organic functional materials.
- the light emitting device of the present invention further comprises a hole injection layer (HIL) or a hole transport layer (HTL) (103) containing the organic HTM or inorganic p type as described above. material.
- HIL hole injection layer
- HTL hole transport layer
- the HIL or HTL can be prepared by printing the printing ink of the present invention, wherein the printing ink contains a functional material having a hole transporting ability, particularly a quantum dot or an organic HTM material.
- the light emitting device of the present invention further comprises an electron injection layer (EIL) or an electron transport layer (ETL) (105) containing the organic ETM or inorganic n-type material as described above.
- EIL electron injection layer
- ETL electron transport layer
- the EIL or ETL can be prepared by printing a printing ink of the present invention, wherein the printing ink contains functional materials having electron transport capabilities, particularly quantum dots or organic ETM materials.
- the invention further relates to the use of the light-emitting device of the invention in various applications, including, but not limited to, various display devices, backlights, illumination sources, and the like.
- the two sides of the bottle were stoppered with a rubber stopper.
- the upper part was connected to a condenser tube, and then connected to a double-row tube, heated to 150 ° C, vacuumed for 40 min, and then passed through a nitrogen gas; 12 mL of a syringe was used.
- ODE was added to a three-necked flask.
- 1.92 mL of the solution 1 was quickly injected into a three-necked flask with a syringe for 12 min.
- After 12 min, 4 mL of the solution was added to the three-necked flask with a syringe.
- solution 1 Weigh 0.0079 g of selenium and 0.1122 g of sulfur in a 25 mL single-necked flask, measure 2 mL of TOP, pass nitrogen, stir, and reserve, hereinafter referred to as solution 1; weigh 0.0128 g of CdO and 0.3670 g of zinc acetate. Take 2.5mL of OA in a 25mL three-necked flask, plug the two sides of the bottle with a rubber stopper, connect a condenser tube at the top, connect to the double-row tube, place the three-necked flask in a 50mL heating jacket, and vacuum the nitrogen.
- the quantum dots were precipitated from the solution with acetone and centrifuged to obtain a quantum dot solid.
- 0.5 g of quantum dot solids were weighed into a glove box, added to the solvent system in the vial, and stirred and mixed. After stirring at a temperature of 60 ° C until the quantum dots were completely dispersed, it was cooled to room temperature.
- the obtained quantum dot solution was filtered through a 0.2 ⁇ m PTFE filter. Seal and store.
- a mixed solvent of 9.5 g of isoquinoline and 3-phenoxytoluene (weight ratio of 60:40) was prepared in a vial.
- 0.5 g of ZnO nanoparticle solids were weighed into a glove box, added to the solvent system in the vial, and stirred and mixed. After stirring at a temperature of 60 ° C until the ZnO nanoparticles were completely dispersed, they were cooled to room temperature.
- the obtained ZnO nanoparticle solution was filtered through a 0.2 ⁇ m PTFE filter. Seal and store.
- organic functional materials referred to in the following examples are all commercially available, such as Jilin O'Reilly. (Jilin OLED Material Technology Co., Ltd, www.jl-oled.com), or synthesized according to the methods reported in the literature.
- the luminescent layer organic functional material comprises a phosphorescent host material and a phosphorescent illuminant material.
- the phosphorescent host material is selected from the group consisting of carbazole derivatives as follows:
- the phosphorescent emitter material is selected from the group consisting of ruthenium complexes as follows:
- the luminescent layer organic functional material comprises a fluorescent host material and a fluorescent illuminant material.
- the fluorescent host material is selected from the group consisting of the following spiro derivatives:
- the fluorescent emitter material is selected from the group consisting of:
- Example 11 Preparation of organic light-emitting layer material containing quinoline and 3-phenoxytoluene
- the luminescent layer organic functional material comprises a host material and a TADF material.
- the host material is selected from the group consisting of the following structures:
- the TADF material is selected from the group consisting of the following structures:
- a mixed solvent of 9.8 g of quinoline and 3-phenoxytoluene (weight ratio of 60:40) was prepared in a vial. 0.19 g of the host material and 0.01 g of the TADF material were weighed in a glove box, added to the solvent system in the vial, and stirred and mixed. After stirring at a temperature of 60 ° C until the organic functional material was completely dissolved, it was cooled to room temperature. The obtained organic functional material solution was filtered through a 0.2 ⁇ m PTFE filter. Sealed and saved
- the printing ink comprises a hole transport layer material having a hole transporting ability.
- the hole transporting material is selected from the following triarylamine derivatives:
- the viscosity of the functional material ink was tested by a DV-IPrime Brookfield rheometer; the surface tension of the functional material ink was tested by a SITA bubble pressure tomometer.
- Example 14 Preparation of an electronic device functional layer using the printing ink of the present invention
- the functional layer in the light-emitting diode such as the light-emitting layer and the charge transport layer, can be prepared by inkjet printing using the printing ink containing the functional material based on the heteroaromatic and organic solvent of the general formula (I) prepared above. Specific steps are as follows.
- the ink containing the functional material is loaded into an ink tank which is mounted on an ink jet printer such as Dimatix Materials Printer DMP-3000 (Fujifilm).
- the waveform, pulse time and voltage of the ejected ink are adjusted to optimize ink ejection and to stabilize within the range of ink ejection.
- the substrate of the OLED/QLED is 0.7 mm thick glass sputtered with an indium tin oxide (ITO) electrode pattern.
- ITO indium tin oxide
- the HIL/HTL material is then inkjet printed into the well and the solvent is removed by drying at elevated temperature in a vacuum to obtain a HIL/HTL film.
- the printing ink containing the luminescent functional material is ink-jet printed onto the HIL/HTL film, and the solvent is removed by drying at a high temperature in a vacuum atmosphere to obtain a luminescent layer film.
- a printing ink containing a functional material having electron transporting properties is ink-jet printed onto the luminescent layer film, and the solvent is removed by drying at a high temperature in a vacuum atmosphere to form an electron transport layer (ETL).
- ETL electron transport layer
- ETL electron transport layer
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Inorganic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Abstract
Description
实施例 | 粘度(cPs) | 表面张力(dyne/cm) |
5 | 5.4±0.5 | 41.0±0.5 |
6 | 5.5±0.5 | 37.2±0.5 |
7 | 4.5±0.3 | 41.7±0.5 |
8 | 4.7±0.3 | 40.1±0.5 |
9 | 5.6±0.5 | 41.3±0.5 |
10 | 5.1±0.5 | 42.1±0.2 |
11 | 5.8±0.5 | 38.3±0.5 |
12 | 5.9±0.5 | 41.6±0.5 |
Claims (20)
- 根据权利要求1所述的用于印刷电子的组合物,其特征在于,其中所述基于杂芳族且具有通式(I)的有机溶剂在25℃下的粘度在1cPs到100cPs的范围内。
- 根据权利要求1所述的用于印刷电子的组合物,其特征在于,所述基于杂芳族且具有通式(I)的有机溶剂在25℃下的表面张力在19dyne/cm到50dyne/cm的范围内。
- 根据权利要求1所述的用于印刷电子的组合物,其特征在于,所述基于杂芳族且具有通式(I)的有机溶剂具有选自如下通式中任一种所示的结构:其中,X是CR1或N;Y选自CR2R3,SiR4R5,NR6,C(=O),S,S(=O)2或O;且每一个通式中至少有一个X或Y是非C的原子;每个所述R1,R2,R3,R4,R5,R6独立选自以下各项中的任一种:H,D,具有1至20个C原子的直链烷基、烷氧基或硫代烷氧基基团,具有3至20个C原子的支链或环状的烷基、烷氧基或硫代烷氧基基团或者是甲硅烷基基团,具有1至20个C原子的取代的酮基基团,具有2至20个C原子的烷氧基羰基基团,具有7至20个C原子的芳氧基羰基基团,氰基基团,氨基甲酰基基团,卤甲酰基基团,甲酰基基团,异氰基基团,异氰酸酯基团,硫氰酸酯基团或异硫氰酸酯基团,羟基基团,硝基基团,CF3基团,Cl,Br,F,具有5至40个环原子的任选取代或未取代的芳族或杂芳族环系,具有5至40个环原子的芳氧基或杂芳氧基基团;其中R1,R2,R3,R4,R5,R6中的一个或多个基团能够彼此和/或与其键合的环形成单环或多环的脂族或芳族环系。
- 根据权利要求1所述的用于印刷电子的组合物,其特征在于,所述R选自:具有1至20个C原子的直链烷基、烷氧基或硫代烷氧基基团,具有3至20个C原子的支链或环状的烷基、烷氧基或硫代烷氧基基团或者是甲硅烷基基团,具有1至20个C原子的取代的酮基基团,具有2至20个C原子的烷氧基羰基基团,具有7至20个C原子的芳氧基羰基基团,氰基基团,氨基甲酰基基团,卤甲酰基基团,甲酰基基团,异氰基基团,异氰酸酯基团,硫氰酸酯基团或异硫氰酸酯基团,羟基基团,硝基基团,CF3基团,Cl,Br,F,具有5至40个环原子的任选取代或未取代的芳族或杂芳族环系,具有5至40个环原子的芳氧基或杂芳氧基基团;其中一个或多个所述R能够彼此和/或与其键合的环形成单环或多环的脂族或芳族环系。
- 根据权利要求1所述的用于印刷电子的组合物,其特征在于,所述基于杂芳族且具有通式(I)的有机溶剂选自:2-苯基吡啶、3-苯基吡啶、4-(3-苯基丙基)吡啶、喹啉、异喹啉、8-羟基喹啉、2-呋喃甲酸甲酯、2-呋喃甲酸乙酯或其中任意两种或以上的混合物。
- 根据权利要求1所述的用于印刷电子的组合物,其特征在于,所述溶剂体系是进一步包含至少一种其它溶剂的混合溶剂,且所述具有通式(I)的有机溶剂占所述混合溶剂总重量的50%以上。
- 根据权利要求1所述的用于印刷电子的组合物,其特征在于,所述功能材料是无机纳米材料。
- 根据权利要求1所述的用于印刷电子的组合物,其特征在于,所述功能材料是量子点材料。
- 根据权利要求1所述的用于印刷电子的组合物,其特征在于,所述功能材料是发光波长位于380nm~2500nm之间的发光量子点材料,其。
- 根据权利要求1所述的用于印刷电子的组合物,其特征在于,所述用于印刷电子的组合物包含有无机功能材料,所述无机功能材料选自:元素周期表IV族、II-VI族、II-V族、III-V族、III-VI族、IV-VI族、I-III-VI族、II-IV-VI族、II-IV-V族的二元或多元半导体化合物中的任一种,或其中任意两种或以上的混合物。
- 根据权利要求1所述的用于印刷电子的组合物,其特征在于,所述功能材料为选自发光钙钛矿纳米材料、金属纳米粒子材料、金属氧化物纳米粒子材料的任一种,或其中任意两种或以上的混合物。
- 根据权利要求1所述的用于印刷电子的组合物,其特征在于,所述功能材料是有机功能材料。
- 根据权利要求14所述的用于印刷电子的组合物,其特征在于,所述有机功能材料为选自空穴注入材料、空穴传输材料、电子传输材料、电子注入材料、电子阻挡材料、空穴阻挡材料、发光体、主体材料或有机染料,或其中任意两种或以上的混合物。
- 根据权利要求14所述的用于印刷电子的组合物,其特征在于,所述有机功能材料包含有至少一种主体材料和至少一种发光体。
- 根据权利要求1所述的用于印刷电子的组合物,其特征在于,所述功能材料占所述用于印刷电子的组合物的重量百分比为0.3%~30%,所述溶剂体系占所述用于印刷电子的组合物的重量百分比为70%~99.7%。
- 一种电子器件,其包含有由如权利要求1所述的用于印刷电子的组合物印刷或涂布而成的功能层。
- 根据权利要求18所述的电子器件,其特征在于,所述电子器件选自以下任一种:量子点发光二极管、量子点光伏电池、量子点发光电池、量子点场效应管、量子点发光场效应管、量子点激光器、量子点传感器、有机发光二极管、有机光伏电池、有机发光电池、有机场效应管、有机发光场效应管、有机激光器或有机传感器。
- 一种功能材料薄膜的制备方法,包括:将根据权利要求1所述的用于印刷电子的组合物,用印刷或涂布的方法铺设于基板上,其中所述印刷或涂布的方法选自以下任一种:喷墨打印、喷印、活版印刷、丝网印刷、浸涂、旋转涂布、刮刀涂布、辊筒印花、扭转辊印刷、平版印刷、柔版印刷、轮转印刷、喷涂、刷涂、移印,或狭缝型挤压式涂布。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201680059869.0A CN108137971B (zh) | 2015-11-12 | 2016-09-23 | 用于印刷电子的组合物及其在电子器件中的应用 |
US15/775,396 US20180320066A1 (en) | 2015-11-12 | 2016-09-23 | Formulation for printed electronics and use of the same in electronic device |
KR1020187016327A KR20180083889A (ko) | 2015-11-12 | 2016-09-23 | 인쇄전자용 조성물 및 전자 장치에서 이의 용도 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201510771747 | 2015-11-12 | ||
CN201510771747.1 | 2015-11-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2017080316A1 true WO2017080316A1 (zh) | 2017-05-18 |
Family
ID=58694713
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2016/099783 WO2017080316A1 (zh) | 2015-11-12 | 2016-09-23 | 用于印刷电子的组合物及其在电子器件中的应用 |
Country Status (4)
Country | Link |
---|---|
US (1) | US20180320066A1 (zh) |
KR (1) | KR20180083889A (zh) |
CN (1) | CN108137971B (zh) |
WO (1) | WO2017080316A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110797466A (zh) * | 2018-08-02 | 2020-02-14 | 中国科学院苏州纳米技术与纳米仿生研究所 | 电子传输层墨水及其制作方法和应用 |
CN115260456A (zh) * | 2021-04-29 | 2022-11-01 | 财团法人工业技术研究院 | 聚合物、含其的量子点组合物及发光装置 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106953030B (zh) * | 2017-03-29 | 2018-11-09 | 京东方科技集团股份有限公司 | 一种薄膜的制作方法、制作设备和显示基板及其制作方法 |
KR102304347B1 (ko) * | 2019-08-30 | 2021-09-23 | 광주과학기술원 | 레이저 기반 멀티인쇄장치 및 이를 이용한 표면 모폴로지가 제어된 대면적 페로브스카이트 박막의 제조방법 |
KR102592869B1 (ko) * | 2020-12-10 | 2023-10-24 | 성균관대학교산학협력단 | 질소-포함 방향족 헤테로 고리를 갖는 화합물을 포함하는 나노 박막, 이의 제조 방법, 및 이를 포함하는 복합 나노 박막 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101180370A (zh) * | 2005-05-20 | 2008-05-14 | 住友化学株式会社 | 聚合物组合物和使用该聚合物组合物的高分子发光器件 |
US20140097406A1 (en) * | 2012-10-04 | 2014-04-10 | Universal Display Corporation | Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers |
CN105038408A (zh) * | 2015-08-14 | 2015-11-11 | 广州华睿光电材料有限公司 | 印刷油墨及应用其印刷而成的电子器件 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20150240103A1 (en) * | 2014-02-25 | 2015-08-27 | E I Du Pont De Nemours And Company | Compositions for high speed printing of conductive materials for electronic circuitry type applications and methods relating thereto |
CN103985822B (zh) * | 2014-05-30 | 2017-05-10 | 广州华睿光电材料有限公司 | 有机混合物、包含其的组合物、有机电子器件及应用 |
-
2016
- 2016-09-23 KR KR1020187016327A patent/KR20180083889A/ko not_active Application Discontinuation
- 2016-09-23 US US15/775,396 patent/US20180320066A1/en not_active Abandoned
- 2016-09-23 CN CN201680059869.0A patent/CN108137971B/zh active Active
- 2016-09-23 WO PCT/CN2016/099783 patent/WO2017080316A1/zh active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101180370A (zh) * | 2005-05-20 | 2008-05-14 | 住友化学株式会社 | 聚合物组合物和使用该聚合物组合物的高分子发光器件 |
US20140097406A1 (en) * | 2012-10-04 | 2014-04-10 | Universal Display Corporation | Aryloxyalkylcarboxylate solvent compositions for inkjet printing of organic layers |
CN105038408A (zh) * | 2015-08-14 | 2015-11-11 | 广州华睿光电材料有限公司 | 印刷油墨及应用其印刷而成的电子器件 |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110797466A (zh) * | 2018-08-02 | 2020-02-14 | 中国科学院苏州纳米技术与纳米仿生研究所 | 电子传输层墨水及其制作方法和应用 |
CN115260456A (zh) * | 2021-04-29 | 2022-11-01 | 财团法人工业技术研究院 | 聚合物、含其的量子点组合物及发光装置 |
CN115260456B (zh) * | 2021-04-29 | 2024-06-04 | 财团法人工业技术研究院 | 量子点组合物及发光装置 |
Also Published As
Publication number | Publication date |
---|---|
US20180320066A1 (en) | 2018-11-08 |
CN108137971B (zh) | 2021-07-06 |
CN108137971A (zh) | 2018-06-08 |
KR20180083889A (ko) | 2018-07-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP3546532B1 (en) | Printing ink composition, preparation method therefor, and uses thereof | |
WO2017080325A1 (zh) | 印刷组合物及其应用 | |
WO2017028640A1 (zh) | 印刷油墨组合物及电子器件 | |
WO2018095380A1 (zh) | 用于印刷电子器件的组合物及其制备方法和用途 | |
WO2017028639A1 (zh) | 印刷油墨及应用其印刷而成的电子器件 | |
CN108352453B (zh) | 电致发光器件、其制备方法及油墨组合物 | |
WO2017080307A1 (zh) | 用于印刷电子器件的组合物及其在电子器件中的应用 | |
WO2017080323A1 (zh) | 印刷组合物及其应用 | |
US20180346748A1 (en) | Formulation for printing electronic device and application thereof in electronic device | |
WO2017080317A1 (zh) | 用于印刷电子的组合物及其在电子器件中的应用 | |
WO2017080316A1 (zh) | 用于印刷电子的组合物及其在电子器件中的应用 | |
WO2017080318A1 (zh) | 印刷电子组合物、包含其的电子器件及功能材料薄膜的制备方法 | |
WO2018103747A1 (zh) | 高聚物及电致发光器件 | |
WO2016091218A1 (zh) | 一种显示器件及其制备方法 | |
US11555128B2 (en) | Printing composition, electronic device comprising same and preparation method for functional material thin film | |
WO2017080324A1 (zh) | 含无机纳米材料的印刷组合物及其应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 16863493 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 15775396 Country of ref document: US |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 20187016327 Country of ref document: KR Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1020187016327 Country of ref document: KR |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 16863493 Country of ref document: EP Kind code of ref document: A1 |