WO2009145504A2 - 광전자 소자용 잉크 조성물 - Google Patents
광전자 소자용 잉크 조성물 Download PDFInfo
- Publication number
- WO2009145504A2 WO2009145504A2 PCT/KR2009/001782 KR2009001782W WO2009145504A2 WO 2009145504 A2 WO2009145504 A2 WO 2009145504A2 KR 2009001782 W KR2009001782 W KR 2009001782W WO 2009145504 A2 WO2009145504 A2 WO 2009145504A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ammonium
- printing
- carbamate
- ink composition
- optoelectronic device
- Prior art date
Links
Images
Classifications
-
- 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
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
- H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
- H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
- H01L21/02288—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating printing, e.g. 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
- H10K71/13—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
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
- H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
-
- 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
-
- 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
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Definitions
- the present invention relates to a printing ink composition that can be applied directly to a patterning process by inking an optoelectronic device material, and more particularly, to an optoelectronic device such as an organic electroluminescent device (OLED) or an organic thin film transistor (OTFT).
- OLED organic electroluminescent device
- OTFT organic thin film transistor
- the present invention relates to a printing ink composition for manufacturing an optoelectronic device, which can be directly patterned by appropriately adjusting the physical properties of a core material when manufacturing a device.
- organic electroluminescent devices are fluorescent or When a current is applied to a device including a phosphorescent light emitting layer, the light emitting device uses a phenomenon in which light is generated by itself when electrons and holes are combined in the light emitting layer.
- the organic light emitting device has a simple structure, a simple manufacturing process, and high quality and wide viewing angle.
- video can be fully realized, high color purity can be realized, and low power consumption and low voltage driving make it suitable for portable electronic devices.
- the detailed structure of the OLED generally includes an anode, a hole injection layer, a hole transfer layer, an emitting layer, an electron transport layer, and an electron injection on a substrate.
- a layer (eletron injection layer), a cathode (cathode) is formed by stacking in order.
- ITO Indium Tin Oxide
- the organic thin film is composed of several layers between the two electrodes as described above in order to increase the luminous efficiency and lifetime. Since the organic thin film is very weak against moisture and oxygen in the air, an encapsulating film is formed on the top to increase the life of the device.
- the inkjet printing process is a technology that can replace the existing deposition process, which is different from the existing deposition process, and has low material consumption, efficient, large area, and low temperature process.
- flexible substrates such as plastic films can be used, which is a printing process technology that can ultimately lower the price of devices, and is being researched and developed by leading organizations as well as domestic and foreign companies.
- the inkjet technology is expected to be used in various fields such as electric, electronic, energy, display, and bio industries, and contribute to the environment-friendly as well as product diversification and cost reduction.
- Inkjet printing technology is a low noise, low cost non-contact printing method, and is classified into continuous jet method and drop-on-demand method according to the injection method.
- Continuous injection method is a method of printing by adjusting the direction of the ink by changing the electromagnetic field during the continuous jet of ink using a pump.
- Drop-on-demand (DOD) is a method of spraying ink only when necessary through an electrical signal.
- a piezoelectric inkjet generates pressure by using a piezoelectric plate that is mechanically deformed by electricity. It is divided into a thermal inkjet method using a pressure generated from the expansion of the bubble generated by the method and heat.
- the properties of the ink composition for applying electroluminescence, electron transport or hole transport organic materials, which are the core materials of optoelectronic devices such as OLEDs, to the inkjet process include optimum viscosity, surface tension, solubility, and uniformity of the film after drying. These required properties affect the droplet forming mechanism and droplet size and speed at constant pressure. For example, in the case of using a conventional inkjet equipment for optoelectronic devices, the optimum viscosity condition of the ink is usually maintained in the viscosity range of 5-15cps to have a good ejectability.
- Korean Patent Laid-Open Publication No. 2003-0058767 discloses in forming a organic light emitting layer of an organic EL device by a roll coating method, a first solvent having a solubility of 1 wt / vv%, a second solvent having a volatility of 0.1 or less, and a surface tension
- a method of improving the printability of the deposited organic light emitting layer by preventing a solvent from evaporating before coating on a substrate by using a mixture composed of a third solvent of 30 dyne / cm or less as a solvent has been proposed. .
- the manufacturing method according to the patent is limited to improving the solubility characteristics of the organic polymer material in a specific process, it is not easy to select a combination of solvents according to the type of organic polymer material, it is easy to control the viscosity suitable for the printing process There is a problem that is difficult to apply to a variety of materials for manufacturing optoelectronic devices.
- the conventional ink composition for optoelectronic device manufacturing is difficult to control the viscosity, solubility, and uniformity of the film forming layer to the extent that it can be applied to printing methods such as inkjet printing, so that the process of inking the optoelectronic material and forming a film by the printing method is part of the organic light emitting layer.
- the process of inking the optoelectronic material and forming a film by the printing method is part of the organic light emitting layer.
- the present invention is an ink composition for ink-printing and printing the core material for optoelectronic devices, the compound of a special structure when printing the ink for the core material for optoelectronic devices such as organic light emitting device (OLED), organic thin film transistor (OTFT), etc. It is to provide a printing ink composition that serves to easily adjust the viscosity, solubility, film uniformity, etc. of the ink, and easy to decompose even at a sufficiently low temperature and does not affect the properties of the optoelectronic device manufactured. have.
- the present invention is intended to enable the flexible and large area of the device and to realize the low cost of the device by applying the printing ink composition to the core material for various optoelectronic devices.
- the present invention has been successfully conducted as a result. That is, when the ammonium carbamate-based compound or ammonium carbonate-based compound is included in the printing ink composition for optoelectronic devices such as OLED or OTFT, the viscosity, solubility, film uniformity, etc. of the ink can be easily controlled.
- the ammonium carbamate-based compound or ammonium carbonate-based compound of the present invention does not decompose itself even at a sufficiently low temperature after performing its role, it does not affect the important functions of the device in the end, thereby improving efficiency and life characteristics. Many of these compounds, which were not available as printing inks, were successfully inkled to enable the printing process, ultimately enabling flexible and large areas of the device, as well as lower cost of the device. It became.
- the present invention relates to a printing ink composition for manufacturing an optoelectronic device, which can be applied to a direct pattern process by inkizing the material of the optoelectronic device, and more particularly, for an optoelectronic device such as an organic light emitting device (OLED) or an organic thin film transistor (OTFT).
- OLED organic light emitting device
- OTFT organic thin film transistor
- the present invention relates to an ink composition for printing containing an ammonium carbamate compound of Formula 1, an ammonium carbonate compound of Formula 2, an ammonium bicarbonate compound of Formula 3, or a mixture thereof when printing a core material. .
- R 1 to R 6 independently represent hydrogen, a hydroxy group, a cycloalkyl group of C 1 -C 30 alkoxy group, C 1 -C 30 alkyl, C 3 -C 30 a, C 6 - an aryl group of C 20, and (C 6 -C 20) aralkyl (C 1 -C 30) alkyl group, or selected from an alkyl group of a functional group-substituted C 1 -C 30, a C 6 -C 20 aryl group substituted with a functional group , Heterocyclic compounds, high molecular compounds and high molecular compound derivatives, or when R 1 to R 6 is a substituted or unsubstituted alkyl group or aralkyl group may include a hetero element selected from N, S, O in the carbon chain And R 1 and R 2 , or R 4 and R 5 , independently of each other, may be connected to an alkylene containing or not containing a hetero
- R 1 to R 6 may be specifically, for example, hydrogen, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, amyl, hexyl, ethylhexyl, heptyl, octyl, isooctyl, Nonyl, decyl, dodecyl, hexadecyl, octadecyl, docodecyl, cyclopropyl, cyclopentyl, cyclohexyl, cholesteryl, allyl, hydroxy, methoxy, methoxyethyl, methoxypropyl, cyanoethyl, e Methoxy, butoxy, hexyloxy, methoxyethoxyethyl, methoxyethoxyethoxyethyl, hexamethyleneimine, morpholine, piperidine, piperazine, ethylene
- Ammonium carbamate compound of Formula 1 is, for example, ammonium carbamate, ethyl ammonium ethyl carbamate, isopropyl ammonium isopropyl carbamate, n-butylammonium n-butyl carbamate, isobutylammonium iso Butyl carbamate, t-butylammonium t-butyl carbamate, 2-ethylhexyl ammonium 2-ethylhexyl carbamate, octadecyl ammonium octadecyl carbamate, 2-methoxyethylammonium 2-methoxyethylcarbamate, 2- Cyanoethylammonium 2-cyanoethylcarbamate, dibutylammonium dibutylcarbamate, dioctadecylammonium dioctadecylcarbamate, methyldecylammoni
- ammonium carbonate-based compound of Formula 2 examples include ammonium carbonate and ethyl.
- At least one of R 1 to R 6 which is a substituent, is a substituent having 1 to 20 carbon atoms, preferably 3 to 20 carbon atoms, in terms of compatibility with organic solvents and degradability at low temperatures. More preferred.
- the method for producing such ammonium carbamate-based or ammonium carbonate-based compound need not be particularly limited.
- It can be prepared from carbon dioxide and carbon dioxide, where it is prepared directly without solvent at atmospheric pressure or pressure, or when using a solvent, alcohols such as methanol, ethanol, isopropanol, butanol, glycols such as ethylene glycol and glycerin, ethyl acetate , Butyl acetate, acetates such as carbitol acetate, diethyl ether, tetrahydrofuran, ethers such as dioxane, methyl ethyl ketone, ketones such as acetone, hydrocarbons such as hexane, heptane, aromatics such as benzene, toluene And halogen-substituted solvents such as chloroform, methylene chloride, carbon tetrachloride, and the like. It may be bubbling or using solid dry ice and reacting even in supercritical conditions.
- any known method may be used to prepare the ammonium carbamate-based or ammonium carbonate-based derivatives used in the present invention as long as the final material has the same structure. That is, it does not need to specifically limit the solvent, reaction temperature, a concentration, or a catalyst for manufacture, and can also manufacture yield.
- the content of the compounds of the formulas (1) to (3) or mixtures thereof contained in the printing ink composition for manufacturing an optoelectronic device according to the present invention does not need to be particularly limited as long as it matches the properties of the printing ink composition of the present invention.
- the content is 0.01 to 90% by weight, more preferably 0.05 to 90% by weight, even more preferably 0.1 to 70% by weight relative to the total weight of the printing ink composition. If the content is less than 0.01% by weight, the effect of the addition of the compound may be insignificant. If the content is more than 90% by weight, the content of other components such as optoelectronic material, solvent, etc. is excessively reduced, so that the desired physical properties after film formation Can be difficult to get.
- the printing ink composition for manufacturing an optoelectronic device is a solvent, a stabilizer, a dispersant, a binder resin, a reducing agent, a surfactant, a wetting agent, if necessary, in addition to the compound of Formulas 1 to 3 or a mixture thereof.
- the solvent contained in the composition need not be particularly limited as long as it meets the printing ink composition properties of the present invention.
- Alcohols such as water, ethanol and methanol, glycols such as ethylene glycol, esters such as methyl acetate and ethyl acetate, ethers such as diethyl ether, tetrahydrofuran, anisole and methyl anisole, acetone and methyl ethyl Ketones such as ketones and acetophenones, aliphatic hydrocarbons such as hexane and heptane, aromatic hydrocarbons such as benzene, toluene, xylene, tetrahydronaphthalene or halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride and chlorobenzene You can use more than one.
- the printing ink composition according to the present invention contains a material for manufacturing an optoelectronic device, and if solubility in a solvent, such as a material for manufacturing an optoelectronic device such as an organic light emitting device (OLED) or an organic thin film transistor (OTFT), or an optoelectronic functional material
- a material for manufacturing an optoelectronic device such as an organic light emitting device (OLED) or an organic thin film transistor (OTFT), or an optoelectronic functional material
- OLED organic light emitting device
- OTFT organic thin film transistor
- Any of organic materials, organic-inorganic hybrids, and organometallic complexes commonly used in the conventional optoelectronic devices may be used, and various structures and functional materials, which have been difficult to directly ink for pattern printing, may be used.
- the material for preparing the optoelectronic device may include a polythiophene-based polymer, a poly-p-phenylene-based polymer, a poly-p-phenylenevinylene-based polymer, Polyfluorene-based, Polycyanopolymers-based, Polyaniline-based, Polyquinoline-based, Polyvinylcarbazole (PVK) -based, Polypyrrole-based homopolymers and polyflu Copolymers having two or more repeating units, such as orylenevinylene, poly-spirofluroene, and polyarylaminevinylene, and various polymers for increasing solubility such as PEDOT / PSS Derivatives, electroluminescent polymers such as green light-emitting polymers (Merck's SPG-020), or charge-transporting polymer materials, and low molecular weight 4,4 ', 4 "-tris (N- (2-naphthyl) -N-phenyl
- light emitting materials hole injection materials, hole transport materials, electron transport materials, electron injection materials, etc., which are the core materials of OLEDs, and representative organic semiconductor materials, conductive polymer materials, and dielectric materials of OTFT are shown, for example. As shown in.
- the core materials constituting the OLED and OTFT in addition to the core materials used in the organic optoelectronic device, such as optical disk material, photochromic material, PHB (Photochemical Hole Burning) material, liquid crystal material, laser pigment material, linear And nonlinear optical materials, resist materials, photosensitive materials, photographic materials, photoconductive materials, organic solar cell materials, electrically conductive materials, electrochromic materials, ion conductive materials, pyroelectrocity materials, charge transfer complex materials, dielectric materials, piezoelectric Materials such as piezoelectrocity, sensor material, magnetic material, optoelectronic functional biomaterial, etc., which have previously been difficult to print, can be easily used for device fabrication. Representative structural examples of these materials are shown in Table 2, and derivatives substituted with appropriate substituents for their structures may be more usefully used in the manufacture of ink for efficiency of devices such as adhesion and thin film properties.
- N and m of the materials described in Table 1 and Table 2 are positive integers, the substituent (R) need not be limited, for example independently alkyl, aryl, heteroaryl, alkoxy, alkylcarbonyl, Trialkylsilylalkylcarbonyl groups, imine groups, ether groups, ester groups, nitrile groups, thioalkoxy groups, thioester groups, amino groups, vinyl groups, halogen elements and the like.
- an organic light emitting diode (OLED) or organic thin film transistor (OTFT) material may be any of fluorescence, phosphorescence, charge transport, electron transport, low molecular weight, dendrimer, oligomer, polymer, and hybrid. . It can also be used in a variety of mixed forms, such as using one or more of these selected.
- the printing ink composition according to the present invention is a coating method such as spin coating, roll coating, spray coating, dip coating, flow coating, doctor blade and dispensing, etc. Although it can be applied to a printing process, it is preferable to apply to a printing process that can be patterned at the same time as coating, and the printing method is not only inkjet printing, but also offset printing, gravure printing, gravure-offset printing, flexography. Printing, screen printing, pad printing, micro contact printing, stencil printing, imprinting and the like.
- the ammonium carbamate-based or ammonium carbonate-based compound included in the printing ink composition for an optoelectronic device according to the present invention can easily control the viscosity of the ink, the solubility of the material for preparing the optoelectronic device, the film uniformity, and the like. After printing, they decompose themselves even at sufficiently low temperatures, which ultimately has no effect on the device's important functions. By making the printing process successful for many compounds that have excellent efficiency and lifetime characteristics but have not been able to use as printing inks, the device is not only flexible and large in area, but also low in cost. It has a big effect on cost.
- TGA Thermal Gravimetric Analysis
- Example 2 is a surface uniformity AFM (Atomic Force Microscope) graph of the surface formed by printing the composition of Example 1,
- Figure 3 shows a light emission picture of the pattern formed by printing the composition of Example 4.
- PEDOT / PSS Poly (3,4-ethylenedioxythiophene / poly (styrene sulfonate)
- Preparation Example 1 1 gram, 3 grams of ethanol (manufactured by Aldrich) were added, stirred at room temperature for 10 minutes, and filtered using a 0.2 micron membrane filter to prepare an inkjet composition.
- the results for tension, printability, and surface uniformity are shown in Table 3. Inkjet printability was used with the DMP-2813 equipment.
- the printability was evaluated by printing 80 nm thick on glass substrates and drying at 150 ° C for 10 minutes. As shown in Fig. 2, the uniformity of the surface formed after inkjet printing by AFM (Atomic Force Microscope) was confirmed, and the average Ra value was 1.23 nm. have.
- Inkjet printability was used in the DMP-2813 equipment and was evaluated in the same manner as in Example 1.
- An emission photo of the pattern formed by inkjet printing the composition of the present embodiment is shown in FIG. 3. It can be seen from the results of FIG. 3 that the green light emission phenomenon is well represented.
- PEDOT / PSS Poly (3,4-ethylenedioxythiophene / poly (styrene sulfonate)
- Aldrich Poly (3,4-ethylenedioxythiophene / poly (styrene sulfonate)
- Preparation Example 1 80 grams, 30 grams of ethanol (manufactured by Aldrich) were added, stirred at room temperature for 30 minutes, and then filtered using a 0.2 micron membrane filter to prepare a composition for flexo printing.
- Table 3 Evaluation of printability was printed on PET with 80 nm thickness, dried at 150 ° C for 10 minutes, and the surface uniformity was confirmed.
- Example 2 contains normal-butyl ammonium normal-butyl carbamate, the viscosity is suitable for application to inkjet printing and printability It is excellent and it can be seen that the roughness of the surface formed after printing is significantly improved.
- the composition of Example 7 has a high viscosity and excellent printability by the gravure printing method, compared to the composition of Comparative Example 2, surface uniformity It can be seen that is significantly improved.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Thin Film Transistor (AREA)
Abstract
Description
Claims (7)
- 광전자 소자용 소재를 잉크화시켜 직접 패턴공정에 적용 가능한 광전자 소자 제조용 프린팅 잉크 조성물에 있어서,상기 프틴팅 잉크 조성물은 하기 화학식 1, 화학식 2 및 화학식 3에서 선택되는 화합물 또는 이들의 혼합물을 조성물 총 중량에 대하여 0.01~90중량%로 함유하는 광전자 소자 제조용 프린팅 잉크 조성물.[화학식 1][화학식 2][화학식 3][상기 화학식 1 내지 화학식 3에서, R1 내지 R6는 서로 독립적으로 수소, 히드록시기, C1-C30의 알콕시기 , C1-C30의 알킬기, C3-C30의 시클로알킬기, C6-C20의 아릴기 및 (C6-C20)아르(C1-C30)알킬기로부터 선택되거나, 관능기가 치환된 C1-C30의 알킬기, 관능기가 치환된 C6-C20의 아릴기, 헤테로고리 화합물, 고분자화합물 및 고분자화합물 유도체로부터 선택되거나, R1 내지 R6 이 관능기가 치환되거나 치환되지 않은 알킬기 또는 아르알킬기일 경우 탄소사슬 내에 N, S, O로부터 선택되는 헤테로원소를 포함할 수 있고, R1과 R2, 또는 R4와 R5 는 서로 독립적으로 헤테로 원자가 포함되거나 포함되지 않은 알킬렌으로 연결되어 고리를 형성할 수 있다.]
- 제 1항에 있어서,R1 내지 R6는 서로 독립적으로 수소, 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, 아밀, 헥실, 에틸헥실, 헵틸, 옥틸, 이소옥틸, 노닐, 데실, 도데실, 헥사데실, 옥타데실, 도코데실, 시클로프로필, 시클로펜틸, 시클로헥실, 알릴, 히드록시, 메톡시, 메톡시에틸, 메톡시프로필, 시아노에틸, 에톡시, 부톡시, 헥실옥시, 메톡시에톡시에틸, 메톡시에톡시에톡시에틸, 헥사메틸렌이민, 모폴린, 피페리딘, 피페라진, 에틸렌디아민, 프로필렌디아민, 헥사메틸렌디아민, 트리에틸렌디아민, 피롤, 이미다졸, 피리딘, 카르복시메틸, 트리메톡시실릴프로필, 트리에톡시실릴프로필, 페닐, 메톡시페닐, 시아노페닐, 페녹시, 톨릴, 벤질, 폴리알릴아민, 폴리에틸렌아민 및 그들의 유도체에서 선택되는 광전자 소자 제조용 프린팅 잉크 조성물.
- 제 1항에 있어서,상기 화학식 1의 암모늄 카바메이트계 화합물은 암모늄 카바메이트(ammonium carbamate), 에틸암모늄 에틸카바메이트, 이소프로필암모늄 이소프로필카바메이트, n-부틸암모늄 n-부틸카바메이트, 이소부틸암모늄 이소부틸카바메이트, t-부틸암모늄 t-부틸카바메이트, 2-에틸헥실암모늄 2-에틸헥실카바메이트, 옥타데실암모늄 옥타데실카바메이트, 2-메톡시에틸암모늄 2-메톡시에틸카바메이트, 2-시아노에틸암모늄 2-시아노에틸카바메이트, 디부틸암모늄 디부틸카바메이트, 디옥타데실암모늄 디옥타데실카바메이트, 메틸데실암모늄 메틸데실카바메이트, 헥사메틸렌이민암모늄 헥사메틸렌이민카바메이트, 모폴리늄 모폴린카바메이트, 피리디늄 에틸헥실카바메이트, 트리에틸렌디아미늄 이소프로필바이카바메이트, 벤질암모늄 벤질카바메이트, 트리에톡시실릴프로필암모늄 트리에톡시실릴프로필카바메이트 및 그 유도체로 이루어진 군으로부터 선택된 1종 또는 2종 이상의 혼합물이고, 상기 화학식 2의 암모늄 카보네이트계 화합물은 암모늄 카보네이트(ammonium carbonate), 에틸암모늄 에틸카보네이트, 이소프로필암모늄 이소프로필카보네이트, n-부틸암모늄 n-부틸카보네이트, 이소부틸암모늄 이소부틸카보네이트, t-부틸암모늄 t-부틸카보네이트, 2-에틸헥실암모늄 2-에틸헥실카보네이트, 2-메톡시에틸암모늄 2-메톡시에틸카보네이트, 2-시아노에틸암모늄 2-시아노에틸카보네이트, 옥타데실암모늄 옥타데실카보네이트, 디부틸암모늄 디부틸카보네이트, 디옥타데실암모늄 디옥타데실카보네이트, 메틸데실암모늄 메틸데실카보네이트, 헥사메틸렌이민암모늄 헥사메틸렌이민카보네이트, 모폴린암모늄 모폴린카보네이트, 벤질암모늄 벤질카보네이트, 트리에톡시실릴프로필암모늄 트리에톡시실릴프로필카보네이트, 트리에틸렌디아미늄 이소프로필카보네이트, 및 그 유도체로부터 선택되는 1종 또는 2종 이상의 혼합물이고, 상기 화학식 3의 암모늄 바이카보네이트계 화합물은 암모늄 바이카보네이트(ammonium bicarbonate), 이소프로필암모늄 바이카보네이트, t-부틸암모늄 바이카보네이트, 2-에틸헥실암모늄 바이카보네이트, 2-메톡시에틸암모늄 바이카보네이트, 2-시아노에틸암모늄 바이카보네이트, 디옥타데실암모늄 바이카보네이트, 피리디늄 바이카보네이트, 트리에틸렌디아미늄 바이카보네이트 및 그 유도체로부터 선택되는 1종 또는 2종 이상의 혼합물인 광전자 소자 제조용 프린팅 잉크 조성물.
- 제 1항에 있어서,상기 광전자 소자는 유기 전기발광 소자(OLED) 또는 유기박막트랜지스터(OTFT)인 광전자 소자 제조용 프린팅 잉크 조성물.
- 제 1항에 있어서,상기 광전자 소자용 소재는 형광고분자, 인광고분자, 호스트물질, 도판트물질, 정공수송재료, 전자수송재료, 유기반도체 재료, 광디스크재료, 광변색재료, PHB(Photochemical Hole Burning)재료, 액정재료, 레이저색소, 광학재료, 레지스트재료, 감광재료, 사진재료, 광도전재료, 전하이동착체, 이온전도성재료, 초전도재료, 센서재료, 전기변색재료, 압전재료, 자성재료, 광전자기능 생체재료, 유기태양전지재료 및 이들의 혼합물로부터 선택되는 광전자 소자 제조용 프린팅 잉크 조성물.
- 제 1항에 있어서,상기 프린팅 잉크 조성물은 잉크젯 프린팅, 옵셋 프린팅, 스크린 프린팅, 패드(pad) 프린팅, 그라비아 프린팅, 플렉소(flexography) 프린팅, 스텐실 프린팅 및 임프린팅(imprinting)으로부터 선택되는 프린팅 방법으로 사용되는 광전자 소자 제조용 프린팅 잉크 조성물.
- 제 1항에 있어서,상기 프린팅 잉크 조성물은 용매, 안정제, 분산제, 바인더 수지(binder resin), 환원제, 계면활성제(surfactant), 습윤제(wetting agent), 칙소제(thixotropic agent) 및 레벨링(levelling)제에서 선택되는 하나 이상의 성분을 더 포함하는 광전자 소자 제조용 프린팅 잉크 조성물.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2011503901A JP5154690B2 (ja) | 2008-04-10 | 2009-04-07 | 光電子素子用インク組成物 |
CN2009801167856A CN102027079B (zh) | 2008-04-10 | 2009-04-07 | 光电子器件用油墨组合物 |
US12/936,871 US20110024668A1 (en) | 2008-04-10 | 2009-04-07 | Ink Composition for Optoelectronic Device |
US14/107,620 US9786843B2 (en) | 2008-04-10 | 2013-12-16 | Methods for fabricating an optoelectronic device |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR20080033386A KR100934752B1 (ko) | 2008-04-10 | 2008-04-10 | 광전자 소자용 잉크 조성물 |
KR10-2008-0033386 | 2008-04-10 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/936,871 A-371-Of-International US20110024668A1 (en) | 2008-04-10 | 2009-04-07 | Ink Composition for Optoelectronic Device |
US14/107,620 Division US9786843B2 (en) | 2008-04-10 | 2013-12-16 | Methods for fabricating an optoelectronic device |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2009145504A2 true WO2009145504A2 (ko) | 2009-12-03 |
WO2009145504A3 WO2009145504A3 (ko) | 2010-01-21 |
Family
ID=41377740
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2009/001782 WO2009145504A2 (ko) | 2008-04-10 | 2009-04-07 | 광전자 소자용 잉크 조성물 |
Country Status (6)
Country | Link |
---|---|
US (2) | US20110024668A1 (ko) |
JP (1) | JP5154690B2 (ko) |
KR (1) | KR100934752B1 (ko) |
CN (1) | CN102027079B (ko) |
TW (2) | TWI530537B (ko) |
WO (1) | WO2009145504A2 (ko) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100922810B1 (ko) | 2007-12-11 | 2009-10-21 | 주식회사 잉크테크 | 흑화 전도성 패턴의 제조방법 |
EP2559078A1 (en) * | 2010-04-12 | 2013-02-20 | Merck Patent GmbH | Composition having improved performance |
JP6015073B2 (ja) * | 2012-04-02 | 2016-10-26 | セイコーエプソン株式会社 | 機能層形成用インク、発光素子の製造方法 |
JP6331349B2 (ja) * | 2013-11-19 | 2018-05-30 | セイコーエプソン株式会社 | 機能層形成用インク、有機エレクトロルミネッセンス素子の製造方法 |
JP2017531049A (ja) | 2014-07-25 | 2017-10-19 | カティーバ, インコーポレイテッド | 有機薄膜インク組成物および方法 |
KR20170015813A (ko) * | 2015-07-31 | 2017-02-09 | 주식회사 잉크테크 | 금속 카바메이트 전구체를 이용한 세라믹 잉크 또는 세라믹 피그먼트의 제조방법과 이에 의해 제조되는 세라믹 잉크 또는 세라믹 피그먼트 |
CN105038408B (zh) * | 2015-08-14 | 2020-01-07 | 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 |
KR20180048690A (ko) | 2015-08-31 | 2018-05-10 | 카티바, 인크. | 디- 및 모노(메트)아크릴레이트 기초 유기 박막 잉크 조성물 |
CN108431143A (zh) * | 2015-12-16 | 2018-08-21 | 默克专利有限公司 | 含固体溶剂的制剂 |
JP6661365B2 (ja) * | 2015-12-17 | 2020-03-11 | 東芝テック株式会社 | インクジェットインク並びに有機薄膜太陽電池の製造方法及び製造装置 |
WO2017218895A1 (en) * | 2016-06-17 | 2017-12-21 | Lawrence Livermore National Security, Llc | Laser gain media fabricated via direct ink writing (diw) and ceramic processing |
KR20180021278A (ko) * | 2016-08-18 | 2018-03-02 | 주식회사 잉크테크 | 금속 전구체 및 세라믹 안료를 포함하는 세라믹 잉크의 제조방법 및 이에 의해 제조되는 세라믹 잉크 |
WO2018070679A1 (ko) * | 2016-10-13 | 2018-04-19 | 주식회사 엘지화학 | 유기트랜지스터 및 가스센서 |
CN111788265B (zh) | 2017-04-21 | 2024-04-23 | 柯狄公司 | 用于形成有机薄膜的组合物和技术 |
US11024827B2 (en) | 2017-05-24 | 2021-06-01 | Lg Chem, Ltd. | Organic electronic device |
JP7194467B1 (ja) | 2021-10-29 | 2022-12-22 | ニタコンサルタント株式会社 | 水検知センサ及びこれに用いる水電池並びに冠水検知方法 |
CN115340463B (zh) * | 2022-08-24 | 2023-12-26 | 温州大学新材料与产业技术研究院 | 磷光主体化合物及其制备方法、磷光材料和应用 |
CN115558399B (zh) * | 2022-10-14 | 2023-11-07 | 江苏中新瑞光学材料有限公司 | 一种耐候电致变色涂料及其制备方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4600598A (en) * | 1983-07-11 | 1986-07-15 | The Lilly Company | Conductive coatings |
JPS61163975A (ja) * | 1985-01-16 | 1986-07-24 | Nissan Chem Ind Ltd | 導電性塗料組成物 |
JPH06248212A (ja) * | 1993-02-26 | 1994-09-06 | Canon Inc | インク、これを用いたインクジェット記録方法及びかかるインクを用いた機器 |
US6288141B1 (en) * | 2000-04-03 | 2001-09-11 | Xerox Corporation | Ink compositions |
KR20080013207A (ko) * | 2006-08-07 | 2008-02-13 | 주식회사 잉크테크 | 저저항 금속 패턴 형성방법 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6110265A (en) * | 1999-04-27 | 2000-08-29 | Xerox Corporation | Ink compositions |
EP1086998A3 (en) * | 1999-09-24 | 2002-01-09 | Canon Kabushiki Kaisha | Bubble-jet ink, method of producing ink and ink-jet recording method |
TW503255B (en) * | 1999-09-27 | 2002-09-21 | Ciba Sc Holding Ag | Electroluminescent devices comprising diketopyrrolopyrroles |
JP2002313567A (ja) * | 2001-04-18 | 2002-10-25 | Sony Corp | 有機電界発光素子及びその製造方法 |
US6680578B2 (en) * | 2001-09-19 | 2004-01-20 | Osram Opto Semiconductors, Gmbh | Organic light emitting diode light source |
US6726755B2 (en) * | 2002-02-08 | 2004-04-27 | Xerox Corporation | Ink compositions containing phthalocyanines |
KR20050022188A (ko) | 2003-08-25 | 2005-03-07 | 주식회사 트랜스텍코리아 | 발포성 열전사물 제조방법 |
EP1846422B1 (en) * | 2005-02-07 | 2016-04-13 | Inktec Co., Ltd. | Organic silver complexes, their preparation methods and their methods for forming thin layers |
US7691294B2 (en) * | 2005-03-04 | 2010-04-06 | Inktec Co., Ltd. | Conductive inks and manufacturing method thereof |
KR100712879B1 (ko) * | 2005-04-06 | 2007-04-30 | 주식회사 잉크테크 | 에칭액 조성물 |
KR20060071388A (ko) | 2006-06-06 | 2006-06-26 | 엔알디테크 주식회사 | 패치 안테나를 이용한 밀리미터파 대역용 송수신기 시스템 |
US8282860B2 (en) * | 2006-08-07 | 2012-10-09 | Inktec Co., Ltd. | Process for preparation of silver nanoparticles, and the compositions of silver ink containing the same |
JP4621193B2 (ja) * | 2006-11-24 | 2011-01-26 | キヤノン株式会社 | 液体組成物、インクジェット記録方法、及びインクジェット記録用インクセット |
US20090274834A1 (en) * | 2008-05-01 | 2009-11-05 | Xerox Corporation | Bimetallic nanoparticles for conductive ink applications |
-
2008
- 2008-04-10 KR KR20080033386A patent/KR100934752B1/ko active IP Right Grant
-
2009
- 2009-04-07 US US12/936,871 patent/US20110024668A1/en not_active Abandoned
- 2009-04-07 CN CN2009801167856A patent/CN102027079B/zh not_active Expired - Fee Related
- 2009-04-07 WO PCT/KR2009/001782 patent/WO2009145504A2/ko active Application Filing
- 2009-04-07 JP JP2011503901A patent/JP5154690B2/ja not_active Expired - Fee Related
- 2009-04-08 TW TW098111641A patent/TWI530537B/zh not_active IP Right Cessation
- 2009-04-08 TW TW102138041A patent/TWI530538B/zh not_active IP Right Cessation
-
2013
- 2013-12-16 US US14/107,620 patent/US9786843B2/en not_active Expired - Fee Related
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4600598A (en) * | 1983-07-11 | 1986-07-15 | The Lilly Company | Conductive coatings |
JPS61163975A (ja) * | 1985-01-16 | 1986-07-24 | Nissan Chem Ind Ltd | 導電性塗料組成物 |
JPH06248212A (ja) * | 1993-02-26 | 1994-09-06 | Canon Inc | インク、これを用いたインクジェット記録方法及びかかるインクを用いた機器 |
US6288141B1 (en) * | 2000-04-03 | 2001-09-11 | Xerox Corporation | Ink compositions |
KR20080013207A (ko) * | 2006-08-07 | 2008-02-13 | 주식회사 잉크테크 | 저저항 금속 패턴 형성방법 |
Also Published As
Publication number | Publication date |
---|---|
TW201406875A (zh) | 2014-02-16 |
US20140106492A1 (en) | 2014-04-17 |
TWI530538B (zh) | 2016-04-21 |
KR20090107874A (ko) | 2009-10-14 |
WO2009145504A3 (ko) | 2010-01-21 |
KR100934752B1 (ko) | 2009-12-30 |
JP2011519981A (ja) | 2011-07-14 |
TW201000577A (en) | 2010-01-01 |
CN102027079A (zh) | 2011-04-20 |
JP5154690B2 (ja) | 2013-02-27 |
US20110024668A1 (en) | 2011-02-03 |
TWI530537B (zh) | 2016-04-21 |
US9786843B2 (en) | 2017-10-10 |
CN102027079B (zh) | 2013-07-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2009145504A2 (ko) | 광전자 소자용 잉크 조성물 | |
US6372154B1 (en) | Luminescent ink for printing of organic luminescent devices | |
EP2361915B1 (en) | Novel heterocyclic compound and use thereof | |
US9133211B2 (en) | Dithienobenzodithiophene semiconductive material and electronic device using the same | |
EP1586616B1 (en) | Organic electroluminescence device | |
KR100991112B1 (ko) | 발광 장치 및 그 제작 방법 | |
KR100577262B1 (ko) | 유기전계발광소자 | |
KR101589757B1 (ko) | 전자 주입층으로 아조메틴-리튬-착물을 사용하는 전계발광 소자 | |
KR101548694B1 (ko) | 신규한 피리미딘 유도체와 이를 포함하는 유기 발광 소자 | |
WO2009038413A2 (en) | Polymer, and organic photoelectric device comprising the same | |
KR20090028346A (ko) | 유기 화합물, 및 이를 포함하는 유기광전소자 | |
CN111788707A (zh) | 电子器件用组合物、电子器件用墨及电子器件的制造方法 | |
KR20130135276A (ko) | 유기 전계 발광 소자 | |
KR20070052753A (ko) | 백색광 전계 발광 소자 | |
WO2005082851A2 (en) | Charge transport compounds and electronic devices made with such compounds | |
KR101503938B1 (ko) | 페난트롤린 화합물 및 이를 사용하는 전계발광 소자 | |
WO2020215564A1 (zh) | 有机发光材料及制备方法和应用 | |
WO2010027129A1 (en) | Pyrrole compounds and organic photoelectric device including the same | |
EP3325463A1 (en) | Heterocyclic compounds and their use in electro-optical or opto-electronic devices | |
KR20060084498A (ko) | 비페닐 유도체 및 이를 채용한 유기 전계 발광 소자 | |
CN1820061B (zh) | 有机发射半导体和基质的混合物、它们的用途及包括所述材料的电子元件 | |
JP5520972B2 (ja) | カルバゾール誘導体とそれを用いた有機エレクトロルミネセンス装置及びその製造方法 | |
KR100865661B1 (ko) | 페닐카바졸기를 갖는 고분자 화합물 및 이를 이용한 고분자전계발광소자 | |
KR102289502B1 (ko) | 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 | |
KR101163050B1 (ko) | 복소환 고리를 이루는 벤조안트라센을 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 200980116785.6 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 09754969 Country of ref document: EP Kind code of ref document: A2 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 12936871 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2011503901 Country of ref document: JP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 09754969 Country of ref document: EP Kind code of ref document: A2 |