CN101457050B - Ink combination and method for forming patterns using the ink combination - Google Patents
Ink combination and method for forming patterns using the ink combination Download PDFInfo
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- CN101457050B CN101457050B CN2008101871023A CN200810187102A CN101457050B CN 101457050 B CN101457050 B CN 101457050B CN 2008101871023 A CN2008101871023 A CN 2008101871023A CN 200810187102 A CN200810187102 A CN 200810187102A CN 101457050 B CN101457050 B CN 101457050B
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- 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
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- 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
Abstract
There are provided an ink composition for imprint lithography and roll-printing, which is applied to the formation of a pattern using imprint lithography and roll-printing to play the role of a pattern support, can increase the accuracy of pattern formation by minimizing the occurrence of a swelling phenomenon caused by the ink composition, and can improve yield and the efficiency of the process by increasing the transfer rate of a pattern, and a method of forming a pattern of a display or semiconductor by using the same.
Description
The application requires korean patent application 10-2007-0129813 number and korean patent application 10-2008-0032791 number the right of submitting on April 8th, 2008 in submission on December 13rd, 2007, and its content is introduced by reference at this.
Technical field
Presents relates to ink composite and uses described ink composite to form the method for pattern.
Background technology
Usually, the method that is applied to the formation fine pattern in information storage, Miniature Sensor, optical crystal and optical element, microelectromechanicdevices devices, display unit, indicating meter and the semi-conductor etc. all is the photolithography of using up to form fine pattern by making.
In the photolithography of correlation technique, circuit line width or pattern line-width depend on employed light wavelength in the exposure process.In view of present state of the art, because interference of light is difficult to form the fine pattern that is less than or equal to 70nm at substrate by using photolithography.In addition, along with the superfinishing refinement of pattern, can be such as expensive devices such as exposure apparatuss, this will cause the rising of initial outlay cost and the price hurricane of resolution masks to rise, thereby lower efficiency.The problem that is forced to use the high price device becomes another factor that cost rises the most at last.
In addition, when forming pattern because should expose, the steps such as postexposure bake, development, postdevelopment bake, etching, cleaning, thereby need the very long treatment time.In addition, photoprocess needs repeatedly, has therefore reduced productivity.
As the method that addresses these problems, method for imprint lithography and roll marks (roll-printing) technology has been proposed.Method for imprint lithography is a kind of by making the method that then necessary shape is impressed into described material the formation fine pattern on another material that is used to form pattern on the surface with relatively high-intensity organic materials or polymkeric substance by the people such as the Stephen Chou invention of Princeton university.
More specifically, method for imprint lithography is a kind of technology that forms pattern by following manner: prepare the inorganic or polymeric molds that is formed with required pattern on it, make described die face to the solidification compound that is coated on metallic membrane or the organic membrane, and thermofixation or the described mould of photocuring and described solidification compound.Compare with the photolithography of correlation technique, this method for imprint lithography has advantage aspect processing simplification and the fine pattern formation.
About the roll marks technology, korean patent application 2006-0005482 number (publication 10-2007-76292 communique) disclosed in detail the roll marks device and made the method for display unit by the described device of use.Traditionally, described patent points out that roll printing method is applicable to FED (field-emitter display), organic EL (electroluminescent) device and PDP (Plasmia indicating panel) and manufacturing processed are simplified, even also disclosed the precision that also can guarantee pattern after repeating print.
In the roll marks technology, by using backing plate (blanket) and base plate (clich é), but not be used to form the resolution masks of pattern in the photoetching of correlation technique, pattern directly is transferred to and will forms thereon on the substrate of fine pattern.Described roll marks technology is by using the formation (alignment) as the backing plate of printing stencil (stamp) to make mould improve deformability, and improved productivity and working efficiency by utilizing thermofixation to process.In addition, this technology also is proposed as a kind of alternative method, the complicated technology that is undertaken by plurality of step such as photolithographic exposure, development with abundant minimizing, and reduce the subsidiary technique expenditure that the complicacy because of technique causes.
Yet if use the ink composite with high workability and rate of evaporation when the stamping technique that adopts correlation technique and roll marks technology form fine pattern, described ink composite will be inhaled in the backing plate, thereby cause the pollution of backing plate.It is elongated that this will cause processing idle time, and backing plate access times in use reduce.
In addition, when the impurity on the ink composite that produces for the pollution of removing because of backing plate carried out cleaning operation by physical contact, the surface was damaged because of friction easily.In addition, when impressing in the situation that the ink composite on backing plate is not removed or roll marks when processing, the fine pattern of ink composite will be formed on the substrate-side that will form mistakenly, maybe too much mass defect will occur.Therefore, there is restriction in the continuously transfer printing of fine pattern, and the precision of fine pattern also is difficult to improve.
Summary of the invention
An aspect of presents provides ink composite, and described ink composite comprises: a) 5 weight parts～45 parts by weight polymer resins; B) 5 weight parts～45 weight part tackiness agent; And c) 50 weight parts～90 weight part organic solvents.
Another aspect of presents provides a kind of ink composite, described ink composite is used for by ink composite is contacted with the figuratum backing plate of formation on it method for imprint lithography and the roll printing method of pattern transfer on substrate, wherein said ink composite comprises vibrin, tackiness agent and organic solvent, and backing plate swelling ratio with respect to described ink composite after 24 hours is 0～5%.
Description of drawings
Accompanying drawing helps further to understand the present invention, and it is incorporated into the part that this consists of this specification sheets, and they have illustrated embodiments of the present invention, and is used from explanation principle of the present invention with explanation one.
Fig. 1 and Fig. 2 are the electron scanning micrographs by the surface of the fine pattern that uses the ink composite formation of making according to an embodiment of the invention;
Fig. 3 and Fig. 4 are the electron scanning micrographs by the surface of the fine pattern that uses the ink composite formation of making according to comparative example;
Fig. 5 and Fig. 6 are the electron scanning micrographs by the surface of the fine pattern that uses the ink composite formation of making according to another implementation of the invention; With
Fig. 7 and Fig. 8 are the electron scanning micrographs by the surface of the fine pattern that uses the ink composite formation of making according to comparative example.
Embodiment
Now will be with detailed embodiment of the present invention as a reference, accompanying drawing has been made explanation to embodiment.
Describe according to the specific embodiment of the present invention below with reference to the accompanying drawings.
An embodiment
Ink composite according to the present invention comprises: a) 5 weight parts～45 parts by weight polymer resins; B) 5 weight parts～45 weight part tackiness agent; And c) 50 weight parts～90 weight part organic solvents.Described ink composite has excellent pattern and forms performance, and can by add to be used for improving viscosity and helping to keep the tackiness agent of tackiness to play the effect of pattern upholder, can also improve by the transferring rate that improves pattern productive rate and the efficient of processing.
In ink composite of the present invention, a) fluoropolymer resin can be employed novolac resin or acrylic resin etc. in the ink composite.Novolac resin can be by comprising meta-cresol, p-cresol, 2,3,5-TEP, 2, the polymkeric substance that the aromatic alcohol of 3-dimethylbenzene and 3,5-dimethylbenzene and formaldehyde or polyformaldehyde reaction are synthetic.Acrylic resin then obtains by polymerizable unsaturated monocarboxylic acid, aromatic monomer, Acrylic Acid Monomer etc.
The molecular weight of fluoropolymer resin is preferably 2,000～40, and 000, more preferably 2,000～15,000.
With respect to the composition of 100 weight parts altogether, fluoropolymer resin is preferably 5 weight parts～45 weight parts, more preferably 7 weight parts～12.5 weight parts.In above-mentioned scope, the effect of pattern upholder can be provided, and can improve productive rate and the efficient of processing by the transferring rate that improves pattern.
In addition, in ink composite of the present invention, b) tackiness agent can increase the viscosity of ink composite, helps to keep tackiness, and can increase the deformability of impression and roll marks.In addition, can also provide the effect of pattern upholder, and can improve productive rate and the efficient of processing by the transferring rate that improves pattern.
Specific examples as tackiness agent, can use butylation hydroxybenzene methyl ether, 2,6-di-t-butyl-4-methylolphenol, Yoshinox BHT, Tenox PG, Progallin LA, Stabilizer GA 8,2,4,5-trihydroxy-n-butyrophenone, tertiary butylated hydroquinone, such as the 3-amino-phenol, PAP, the 4-methoxyphenol, 2,3,5-trimethoxy phenol, 2, the 4-xylenol, poly-(4-Vinyl phenol), the phenols such as 4-bromophenol, such as ethyl vinyl ether, poly-(methylvinylether), poly-ethers such as (IVE), poly-(to hydroxyl) vinylbenzene, 1,1-two (4-hydroxy phenyl) decane, 4,4-[1-[4-[1-(1, the 4-hydroxy phenyl)-and the 1-methylethyl] phenyl] ethylidene] bis-phenol, [4, the 4-[2-hydroxy phenyl] methylene radical] two [2,6-xylenol], molecular-weight average is 100～1,500 urethane acrylate, and urethane oligomer, can use separately these compounds, also can use in them two kinds or more than two kinds mixture.
In ink composite of the present invention, the content of tackiness agent is preferably 5 weight parts～45 weight parts, more preferably 7 weight parts～12.5 weight parts.
In above-mentioned scope, the deformability of the tackiness of ink composite and impression, roll marks all is improved, and the effect of pattern upholder can be provided, and productive rate and the efficient that can improve by the transferring rate that improves pattern processing.
In addition, in ink composite of the present invention, c) organic solvent preferably can easily dissolve described fluoropolymer resin, described tackiness agent and the additional organic solvent such as additives such as visible compounds that uses when needing.
Particularly, as organic solvent, can use alcohols such as methyl alcohol, ethanol, ethylene glycol, triethylene glycol, TEG, propylene glycol, Diethylene Glycol, butyleneglycol, phenylcarbinol, hexanol; Ethers such as propylene carbonate, tetrahydrofuran (THF), phenylmethylether, Isosorbide-5-Nitrae-dioxane, 1-methoxy-2-propanol, phenylmethylether, dibutyl ether, phenyl ether; Ester classes such as ethyl acetate, propyl acetate, butylacetate, ethyl propionate, ethyl ester, butyl ester, 2-hydroxy-methyl isobutyl acid, 2-methoxyl group-1-methylethyl ester, 2-methoxy ethyl acetic ester, 2-ethoxyethyl group acetic ester; Ethylene glycol alkyl oxide acetic ester such as Ethylene Glycol Methyl ether acetic acid ester, ethylene glycol monoethyl ether acetate; Such as ethylene glycol alkyl oxide propionic esters such as glycol ethyl ether propionic esters; Ethylene glycol monoalkyl ethers such as Ethylene Glycol Methyl ether, glycol ethyl ether; The alkyl oxide such as the Diethylene Glycol such as diethylene glycol monomethyl ether, TC; Propylene glycol alkyl ether acetic acid esters such as methyl proxitol acetate, propylene glycol ethyl ether acetic ester, propylene glycol propyl ether acetic ester; Propylene glycol alkyl ether propionic esters such as methyl proxitol propionic ester, propylene glycol ethyl ether propionic ester, propylene glycol propyl ether propionic ester; Propylene-glycol monoalky lethers such as methyl proxitol, propylene glycol ethyl ether, propylene glycol propyl ether, propylene glycol butyl ether; Dipropylene glycol alkyl oxides such as dipropylene glycol dimethyl ether, dipropylene glycol Anaesthetie Ether; Butyleneglycol monoalky lethers such as butyleneglycol monomethyl ether, butyleneglycol list ethyl ether; With dibutylene glycol alkyl oxides such as dibutylene glycol dimethyl ether, dibutylene glycol Anaesthetie Ether, can use separately these solvents, also can use in them two kinds or more than two kinds mixture.Especially, be to improve the coating performance on backing plate, uses two kinds or more than the mixture of two kinds of solvents as organic solvent, as organic solvent, more more favourable for pattern transfer than a kind of solvent of use.
In described ink composite, the content of organic solvent is preferably 50 weight parts～90 weight parts, more preferably 70 weight parts～80 weight parts.In above-mentioned scope, can obtain simultaneously solvability and processing efficiency.
The ink composite that is used for imprint lithography and roll marks that is made of said components according to the present invention can further comprise tensio-active agent or additive.
Tensio-active agent plays the effect that prevents forming the effect of printing ink stain or hole trace in backing plate and obtain good coating performance.
Tensio-active agent can comprise silica-based surfactant or boryl tensio-active agent, perfluoroalkyl oligopolymer for example, and with respect to the described ink composite of 100 weight parts altogether, its content is 0.01 weight part～3 weight parts, is preferably 0.1 weight part～1.5 weight parts.
Described additive can comprise viscosity sensitizing agent or visible compound.
The viscosity sensitizing agent is for increasing the viscosity to lower floor.As the viscosity sensitizing agent, can use trimeric cyanamide based cross-linker commonly used.The trimeric cyanamide based cross-linker can comprise the condensation product of condensation product, trimeric cyanamide and the formaldehyde of urea and formaldehyde, and the methylolurea alkyl oxide that is obtained by alcohol or melamine methylol alkyl oxide etc.
Particularly, as the condensation product of urea and formaldehyde, can use monomethylol urea, dimethylolurea etc.As the condensation product of trimeric cyanamide and formaldehyde, can use hexamethylolmelamine.In addition, also can use the part condensation product of trimeric cyanamide and formaldehyde.In addition, the methylolurea alkyl oxide obtains with the alcohol reaction by the part or all of methylol with the condensation product of urea and formaldehyde, and its specific examples comprises monomethyl urea methyl ether, dimethyl urea methyl ether etc.The melamine methylol alkyl oxide obtains with the alcohol reaction by the part or all of methylol with the condensation product of trimeric cyanamide and formaldehyde, and its specific examples comprises hexamethylolmelamine hexamethyl ether, hexamethylolmelamine six butyl ethers etc.The hydrogen atom that in addition, can also use the amino with trimeric cyanamide by the compound of the structure of hydroxymethyl and methoxymethyl displacement, have trimeric cyanamide amino hydrogen atom by the compound of the structure of butoxymethyl and methoxymethyl displacement, etc.Especially, preferably use the melamine methylol alkyl oxide.
If use the viscosity sensitizing agent as additive, then with respect to the described composition of 100 weight parts altogether, advantageously its content is 0.01 weight part～5 weight parts, preferred 0.5 weight part～2.5 weight parts.In above-mentioned scope, ink composite of the present invention has excellent binding property for the substrate of below, and can play the effect of the metal level below the protection pattern in follow-up etch processes.
As seen compound is realized excellent pattern transfer performance by dissolving with fluoropolymer resin, and can be obtained more easily the bounding force to the substrate of needs by using dyestuff, pigment or light-sensitive compound to make ink composite obtain visibility.
As visible compound, can use two triazo-compounds, for example by use that 2-diazo-1-naphthol-5-sulfonic acid esterification trihydroxybenzophenone prepares 2,3,4-trihydroxybenzophenone 1,2-naphthoquinones diazido-5-sulphonate, by use that 2-diazo-1-naphthol-5-sulfonic acid esterification tetrahydroxybenzophenone prepares 2,3,4,4 '-tetrahydroxybenzophenone 1,2-naphthoquinones diazido-5-sulphonates etc. can use separately these compounds, also can use in these compounds two kinds or more than two kinds mixture.
If use visible compound as additive, then with respect to 100 weight parts ink composite of the present invention altogether, advantageously its content is 0.1 weight part～3 weight parts, preferred 0.5 weight part～2.0 weight parts.
The ink composite of the present invention that contains aforementioned component can adopt the conventional stamped method (for example Korean Patent 10-2005-0019557 communique) and the roll printing method (for example Korean Patent 10-2007-0076292 communique) that are widely known by the people to be applied to the formation of pattern, thereby forms pattern at substrate.
In specific embodiment, by appropriate means such as spin coating, roller coat and slot coated the thickness of ink composite with 0.5 μ m～10 μ m is coated with.Then, in impression is processed, after making ink composite and the backing plate printing stencil of the pattern with desired shape contact, with pattern transfer to substrates such as silicon substrate, ceramic substrate, metal level, polymer layer.On the other hand, in roll marks is processed, after the base plate that has the pattern of desired shape by use makes ink composite and backing plate contacts, with pattern transfer to substrates such as silicon substrate, ceramic substrate, metal level, polymer layer.
Next, can process by using ultraviolet ray to carry out photocuring, perhaps under 90 ℃～200 ℃ temperature, carry out processing for heat treated thermofixation, perhaps carry out simultaneously photocuring processing and thermofixation and process.The purpose of heat-treating operation is evaporating solvent under the condition of the solid ingredient of pyrolysis oil ink composition not.Usually, preferably reduce the concentration of solvent by heat treatment step, preferably heat treatment step is proceeded to the thickness of staying the ink film on the substrate and be less than or equal to till the 10 μ m.Above-mentioned operation has increased binding property and the chemical resistant properties between ink film and the substrate.Use etchant solution or gas plasma process to finish the substrate of above-mentioned operation on it, to process the substrate regions that exposes.At this moment, the not exposed region of substrate is protected by ink film.Behind treatment substrate in this way, remove ink film by utilizing suitable stripper, can form meticulous circuit pattern at substrate.
Surpass 24 hours by at room temperature component as shown in table 1 below and composition evenly being mixed, preparation embodiment 1 and 2 and comparative example 1 and 2 and ink composite.Unit in the table 1 is weight part.
In table 1, employed fluoropolymer resin is novolac resin in the embodiment 1 and 2, and organic solvent is methyl alcohol, and tensio-active agent is Silicon surfactant, and additive is hexamethylolmelamine hexamethyl ether.
[table 1]
| Classification | Embodiment 1 | Embodiment 2 | Comparative example 1 | Comparative example 2 |
| Fluoropolymer resin | 10 | 10 | 10 | 20 |
| Tackiness agent | 10 butylation hydroxybenzene methyl ethers | 10 poly-(to hydroxyl) vinylbenzene | 10 urethane acrylates | - |
| Organic solvent | 80 | 80 | 80 | 80 |
| Tensio-active agent | 1 | 1 | 1 | 1 |
| Additive | 3 | 3 | 3 | - |
On the other hand, fluoropolymer resin is acrylic resin, organic solvent is 1,4-dioxane, tensio-active agent are the boron surface promoting agents, and additive is monomethyl urea methyl ether, and can be the mixture of novolac resin and acrylic resin for fluoropolymer resin, organic solvent is 2-methoxy ethyl acetic ester, and tensio-active agent is the boron surface promoting agent, and additive is hexamethylolmelamine six butyl ethers.
Embodiment 1 by preparation in the following method evaluation table 1 and 2 and the physical properties of the ink composite of comparative example 1 and 2.
A. fine pattern transfer rate
With embodiment 1 and 2 and the ink composite of comparative example 1 and 2 be coated on and do not have on the figuratum backing plate.After the seasoning 20 seconds, along with backing plate process base plate, fine pattern is transferred on the substrate that will form, and the transferring rate of pattern is as shown in following table 2.According to the formational situation of pattern in 100 grid that are of a size of 1mm * 1mm, can find out obviously that the transferring rate of pattern is 0～100%.
[table 2]
| Classification | Embodiment 1 | Embodiment 2 | Comparative example 1 | Comparative example 2 |
| Pattern transfer rate (%) | 96 | 95 | 70 | 30 |
As shown in table 2, can find to use ink composite according to the embodiment 1 of tackiness agent of the present invention and 2 to demonstrate pattern transfer rate more than or equal to 95% excellence.
B. pattern forms precision
With embodiment 1 and 2 and the ink composite of comparative example 1 and 2 be coated on and do not have on the figuratum backing plate.After the seasoning scheduled time, along with backing plate process base plate, fine pattern is transferred on the substrate that will form.Next, at high temperature transfer printing on it there is the substrate heat of fine pattern to process the scheduled time, then immerses the scheduled time and dry in 40 ℃ the aluminium etching solution.Then, use the surface of scanning electron microscope analysis fine pattern, its result is presented at respectively table 1 to table 4.In addition, measure the bounding force between the substrate of fine pattern part and below and being presented in the table 3.It is 0～100% that bounding force between the substrate of fine pattern part and below is proved to be according to degree.
, can find that the ink composite of 1 (Fig. 1) and embodiment 2 (Fig. 2) has shown excellent pattern according to the embodiment of the present invention to form precision, because they have all formed uniform pattern to shown in the table 4 such as table 1.On the other hand, in comparative example 1 and comparative example 2, can find that pattern formation does not accurately display.
[table 3]
| Classification | Embodiment 1 | Embodiment 2 | Comparative example 1 | Comparative example 2 |
| Bounding force (%) | 98 | 97 | 5 | 2 |
As shown in table 3, can find that the ink composite of 1 (Fig. 1) and embodiment 2 (Fig. 2) is compared with the ink composite of comparative example 2 with comparative example 1 according to the embodiment of the present invention, shown extremely excellent bounding force.
Another embodiment
The invention still further relates to the method that forms pattern, described method is by ink composite is contacted method for imprint lithography and the roll printing method of pattern transferring on substrate with the figuratum backing plate of formation.Wherein said ink composite comprises fluoropolymer resin, tackiness agent and organic solvent, and backing plate is 0～5% with respect to the swelling ratio of ink composite after 24 hours.Backing plate is 0～5% with respect to the swelling ratio of ink composite after 24 hours.Preferably, described ink composite comprises: a) 5 weight parts～45 parts by weight polymer resins; B) 5 weight parts～45 weight part tackiness agent; And c) 50 weight parts～90 weight part organic solvents.
After 24 hours backing plate with respect to the swelling ratio of ink composite refer to the initial weight of backing plate with backing plate is immersed ink composite after 24 hours with its taking-up and with the difference of the weight of measuring behind the clean methanol and the ratio of the initial weight of backing plate { swelling ratio (%)=[initial weight (g) of (initial weight (g) of the weight of the backing plate after the cleaning (g)-backing plate)/backing plate] * 100}.Backing plate is 0～5% with respect to the swelling ratio of ink composite of the present invention after 24 hours.Preferably, the swelling ratio after 24 hours is 0～4%.
In ink composite of the present invention, a) fluoropolymer resin can be employed novolac resin, acrylic resin etc. in the typical ink composite.Novolac resin can be by comprising meta-cresol, p-cresol, 2,3,5-TEP, 2, the polymkeric substance that the aromatic alcohol of 3-dimethylbenzene and 3,5-dimethylbenzene and formaldehyde or polyformaldehyde reaction are synthetic.Acrylic resin then obtains by polymerizable unsaturated monocarboxylic acid, aromatic monomer, Acrylic Acid Monomer etc.
The molecular weight of fluoropolymer resin is preferably 2,000～100, and 000, more preferably 2,000～45,000.
With respect to the composition of 100 weight parts altogether, fluoropolymer resin is preferably 5 weight parts～45 weight parts, more preferably 7 weight parts～12.5 weight parts.In above-mentioned scope, the effect of pattern upholder can be provided, and can improve productive rate and the efficient of processing by the transferring rate that improves pattern.
In addition, in ink composite of the present invention, b) tackiness agent can increase the viscosity of ink composite, helps to keep tackiness, and can increase the deformability of impression and roll marks.In addition, can also provide the effect of pattern upholder, and can improve productive rate and the efficient of processing by the transferring rate that improves pattern.
Specific examples as tackiness agent, can use butylation hydroxybenzene methyl ether, 2,6-di-t-butyl-4-methylolphenol, Yoshinox BHT, Tenox PG, Progallin LA, Stabilizer GA 8,2,4,5-trihydroxy-n-butyrophenone, tertiary butylated hydroquinone, such as the 3-amino-phenol, PAP, the 4-methoxyphenol, 2,3,5-trimethoxy phenol, 2, the 4-xylenol, 2, the 6-xylenol, poly-(4-Vinyl phenol), the phenols such as 4-bromophenol, such as ethyl vinyl ether, poly-(methylvinylether), poly-ethers such as (IVE), poly-(to hydroxyl) vinylbenzene, 1,1-two (4-hydroxy phenyl) decane, 4,4-[1-[4-[1-(1, the 4-hydroxy phenyl)-and the 1-methylethyl] phenyl] ethylidene] bis-phenol, [4, the 4-[2-hydroxy phenyl] methylene radical] two [2,6-xylenol], four (methylene radical-(3,5-di-t-butyl-4-hydroxyl hydrogenated cinnamate)) methane, 1,3,5-trimethylammonium-2,4,6-three-(3,5-di-t-butyl-4-hydroxybenzene methyl) benzene, three-(3,5-di-t-butyl-4-hydroxybenzene methyl) isocyanuric acid ester, 3-(3 ', 5 '-di-tert-butyl-hydroxy phenyl) the propionic acid stearyl, 2,5-two (1, the 1-dimethyl propyl)-1, the 4-dihydroxy-benzene, 1,1,3-three (2-methyl)-4-hydroxyl-5-tert-butyl-phenyl butane, triethylene glycol-two-(3-tertiary butyl-4-hydroxy-5-aminomethyl phenyl) propionic ester, 2,2-methylene radical two (4-methyl-6-(1-methylcyclohexyl) phenol) and three (2,4-two-tert-butyl-phenyl) phosphoric acid ester, can use separately these compounds, also can use in them two kinds or more than two kinds mixture.In addition, the rosin resin that can also choice and operation be widely known by the people, the rosin that comprises modifications such as the unmodified rosin such as gum resin, wood rosin and starex, the rosin-disproportionating rosin such as polymerization, the rosin of stabilization, complete all hydrogenated rosin, partially hydrogenated rosin, with the rosin of other chemical modification of the modifications such as polymerization by unmodified rosin, disproportionation, hydrogenation, and various rosin derivatives etc.As rosin derivative, can use rosin resin, the rosin ester based resin of unsaturated fatty acids modification, the rosin alcohol based resins of unsaturated fatty acids modification, and the metal-salt of rosin resin.
In addition, can also use molecular-weight average is 1,000～5,000 urethane oligomer, can be used alone, and also can use two kinds or more than two kinds mixture.
In ink composite of the present invention, the content of tackiness agent is preferably 5 weight parts～45 weight parts, more preferably 7 weight parts～12.5 weight parts.In above-mentioned scope, the deformability of the tackiness of ink composite and impression, roll marks all is adjusted, and the effect of pattern upholder can be provided, and productive rate and the efficient that can improve by the transferring rate that improves pattern processing.
In addition, in ink composite of the present invention, c) organic solvent preferably can easily dissolve described fluoropolymer resin, described tackiness agent and the additional organic solvent such as additives such as visible compounds that uses when needing.Backing plate is 0～5% with respect to the swelling ratio of organic solvent after 24 hours.
Preferably, as organic solvent, can use acetonitrile, glycerine, methyl-sulphoxide, Nitromethane 99Min., dimethyl formamide, phenol, N-Methyl pyrrolidone, pyridine perfluor tributylamine, perfluorodecalin, 2-butanone, such as methyl alcohol, ethanol, ethylene glycol, triethylene glycol, TEG, propylene glycol, Diethylene Glycol, butyleneglycol, phenylcarbinol, the alcohols such as hexanol, such as propylene carbonate, tetrahydrofuran (THF), phenylmethylether, 1, the 4-dioxane, the 1-methoxy-2-propanol, phenylmethylether, dibutyl ether, the ethers such as phenyl ether, such as Ethylene Glycol Methyl ether, the ethylene glycol monoalkyl ethers such as glycol ethyl ether, such as diethylene glycol monomethyl ether, TC, diethylene glycol dimethyl ether, the Diethylene Glycol alkyl oxides such as diethylene glycol methyl ethyl ether, such as methyl proxitol, the propylene-glycol monoalky lethers such as propylene glycol butyl ether, such as the dipropylene glycol dimethyl ether, the dipropylene glycol alkyl oxides such as dipropylene glycol Anaesthetie Ether, such as the butyleneglycol monomethyl ether, the butyleneglycol monoalky lethers such as butyleneglycol list ethyl ether, with such as the dibutylene glycol dimethyl ether, the dibutylene glycol alkyl oxides such as dibutylene glycol Anaesthetie Ether, can use separately these solvents, also can use in them two kinds or more than two kinds mixture.Especially, be to improve the coating performance on backing plate, uses two kinds or more than the mixture of two kinds of solvents as organic solvent, as organic solvent, more more favourable for pattern transfer than a kind of solvent of use.
In described ink composite, the content of organic solvent is preferably 50 weight parts～90 weight parts, more preferably 70 weight parts～80 weight parts.In above-mentioned scope, can obtain simultaneously solvability and processing efficiency.
The ink composite that is used for imprint lithography and roll marks that is made of said components according to the present invention can further comprise tensio-active agent or additive, and is such as mentioned above.
Described backing plate is made by PDMS (polydimethylsiloxane).
Surpass 24 hours by at room temperature component as shown in table 4 below and composition evenly being mixed, preparation embodiment 1 and 2 and comparative example 1 and 2 and ink composite.Unit in the table 4 is g.
The fluoropolymer resin that uses in the table 4 is that molecular-weight average is 7,000 novolac resin, tackiness agent are butylation hydroxybenzene methyl ethers, and tensio-active agent is Silicon surfactant, additive is hexamethylolmelamine hexamethyl ether, and the ratio of mixture of organic solvent is weight ratio.
[table 4]
| Classification | Embodiment 1 | Embodiment 2 | Comparative example 1 | Comparative example 2 |
| Fluoropolymer resin | 10 | 10 | 10 | 20 |
| Tackiness agent | 10 | 10 | 10 | - |
| Organic solvent | 80 acetonitriles: triethylene glycol=9:1 | 80 acetonitriles | 80 ethyl acetate: butylacetate=9:1 | 80 ethyl acetate |
| Tensio-active agent | 1 | 1 | 1 | 1 |
| Additive | 3 | 3 | 3 | 3 |
Embodiment 1 by preparation in the following method evaluation table 1 and 2 and the physical properties of the ink composite of comparative example 1 and 2.
A. the swelling ratio of backing plate and ink composite
Backing plate is cut into 50 * 50 size, and with its immerse fully embodiment 1 and 2 and the ink composite of comparative example 1 and 2 in 24 hours, then use clean methanol.Next, according to the ratio measure swelling ratio (%) of initial weight and final weight, the result is as shown in following table 5.
Swelling ratio=[initial weight (g) of (initial weight (g) of the weight of the backing plate after the cleaning (g)-backing plate)/backing plate] * 100.
[table 5]
| Initial weight | Weight after the cleaning (g) | Swelling ratio (%) |
| Embodiment 1 | 4.018 | 4.033 | 0.4 |
| Embodiment 2 | 3.886 | 3.898 | 0.3 |
| Comparative example 1 | 3.985 | 4.048 | 1.6 |
| Comparative example 2 | 3.941 | 3.995 | 1.4 |
As shown in table 5, can find that 1 and 2 ink composite has shown minimum rate of permeation for backing plate according to the embodiment of the present invention, the backing plate in the comparative example 1 and 2 has then shown serious Swelling, and wherein swelling ratio is more than or equal to 1.4.
B. fine pattern transfer rate
With embodiment 1 and 2 and the ink composite of comparative example 1 and 2 be coated on and do not have on the figuratum backing plate.After the seasoning 20 seconds, along with backing plate process base plate, fine pattern is transferred on the substrate that will form, and the transferring rate of pattern is as shown in following table 6.According to the formational situation of pattern in 100 grid that are of a size of 1mm * 1mm, can find out obviously that the transferring rate of pattern is 0～100%.
[table 6]
| Classification | Embodiment 1 | Embodiment 2 | Comparative example 1 | Comparative example 2 |
| Pattern transfer rate (%) | 98 | 96 | 92 | 85 |
As shown in table 6, can find that 1 and 2 ink composite has according to the embodiment of the present invention demonstrated the pattern transfer rate more than or equal to 96% excellence.
B. pattern forms precision
With embodiment 1 and 2 and the ink composite of comparative example 1 and 2 be coated on and do not have on the figuratum backing plate.After seasoning predetermined time, along with backing plate through base plate, fine pattern is transferred on the substrate that will form.Next, thermal treatment on it transfer printing the substrate of fine pattern is arranged, then it is immersed the scheduled time in 40 ℃ the aluminium etching solution, take out and dry.Then, use the surface of scanning electron microscope analysis fine pattern, its result is presented at respectively table 5 to table 8.
, can find that the ink composite of 1 (Fig. 5) and embodiment 2 (Fig. 6) has shown excellent pattern according to the embodiment of the present invention to form precision, because they have all formed uniform pattern to shown in the table 8 such as table 5.On the other hand, in comparative example 1 (Fig. 7) and comparative example 2 (Fig. 8), can find that pattern formation does not accurately display.
D. waiting time of ink composite
With embodiment 1 and 2 and the ink composite of comparative example 1 and 2 be coated on and do not have on the figuratum backing plate.After the seasoning, along with backing plate process base plate, fine pattern is transferred on the substrate that will form.Next, thermal treatment on it transfer printing the substrate of fine pattern is arranged, then it is immersed the scheduled time in 40 ℃ the aluminium etching solution, take out and dry.Then, the transferring rate during according to the formation pattern is measured the waiting time, and is presented in the following table 7.Unit in the table 7 is %.
[table 7]
| Time (second) | 0 | 5 | 10 | 15 | 20 | 25 | 30 | 40 | 90 | 150 |
| Embodiment 1 | 94 | 95 | 98 | 97 | 94 | 95 | 92 | 91 | 90 | 0 |
| Embodiment 2 | 94 | 95 | 93 | 96 | 95 | 94 | 93 | 91 | 90 | 0 |
| Comparative example 1 | 82 | 93 | 95 | 94 | 57 | 42 | 30 | 0 | ||
| Comparative example 2 | 80 | 82 | 84 | 85 | 35 | 20 | 11 | 0 |
As shown in table 7, in the time of can finding that waiting time when 1 and 2 ink composite according to the embodiment of the present invention was less than 90 seconds, it shows excellent pattern transfer rate.On the other hand, can find that when waiting time of the ink composite of comparative example 1 according to the present invention and 2 during less than 30 seconds, the pattern transfer rate that it shows is respectively 30% and 11%, and does not carry out transfer printing after 40 seconds.Therefore, the waiting time that can find ink composite of the present invention has obtained remarkable improvement.
Aforementioned embodiments and advantage only are exemplary, should not be construed as restriction the present invention.This instruction can easily be applied to the device of other type.The explanation of aforementioned embodiments is intended to the explanation of making an explanation property, and they do not restrict the scope of claim.It will be apparent to one skilled in the art that and to carry out multiplely substituting, improving and change.In the claims, method and function items are intended to structure described herein contained and are the execution to described function wherein not only to comprise structural equivalents, also comprise structure of equal value.In addition, word " refers to " that otherwise this restriction should not explained according to 35 USC 112 (6) unless quoted from clearly in the restriction of claims.
Claims (9)
1. ink composite, described ink composite comprises:
A) fluoropolymer resin of 5 weight parts～45 weight parts;
B) tackiness agent of 5 weight parts～45 weight parts; With
C) organic solvent of 50 weight parts～90 weight parts,
It is the viscosity sensitizing agent of 0.5 weight part～2.5 weight parts that described ink composite also comprises with respect to the described ink composite of 100 weight parts altogether,
Wherein, described fluoropolymer resin is one or more fluoropolymer resins that are selected from by the group of novolac resin, acrylic resin and their compositions of mixtures, and
Described ink composite is used for by ink composite is contacted with the figuratum backing plate of formation on it method for imprint lithography of pattern transfer to the substrate,
Wherein, described tackiness agent is one or more tackiness agent that are selected from following group: butylation hydroxybenzene methyl ether, 2,6-two-tertiary butyl-4-methylolphenol, Yoshinox BHT, Tenox PG, Progallin LA, Stabilizer GA 8,2,4,5-trihydroxy-n-butyrophenone, tertiary butylated hydroquinone, the 3-amino-phenol, PAP, the 4-methoxyphenol, 2,3, the 5-pseudocuminol, 2, the 4-xylenol, poly-(4-Vinyl phenol), the 4-bromophenol, ethyl vinyl ether, poly-(methylvinylether), poly-(IVE), poly-(to hydroxyl) vinylbenzene, 1,1-two (4-hydroxy phenyl) decane, and urethane oligomer
Wherein, described viscosity sensitizing agent is the trimeric cyanamide based cross-linker, and described trimeric cyanamide based cross-linker comprises the condensation product of condensation product, trimeric cyanamide and the formaldehyde of urea and formaldehyde, and the methylolurea alkyl oxide or the melamine methylol alkyl oxide that are obtained by alcohol.
2. ink composite as claimed in claim 1, wherein said organic solvent is one or more organic solvents that are selected from following group: alcohols; Ethers; The ester class.
3. ink composite as claimed in claim 1, wherein said organic solvent is one or more organic solvents that are selected from following group: ethylene glycol alkyl oxide acetic ester; Ethylene glycol alkyl oxide propionic ester; Ethylene glycol monoalkyl ether; The Diethylene Glycol alkyl oxide; Propylene glycol alkyl ether acetic acid ester; Propylene glycol alkyl ether propionic ester; Propylene-glycol monoalky lether; The dipropylene glycol alkyl oxide; The butyleneglycol monoalky lether; With the dibutylene glycol alkyl oxide.
4. ink composite as claimed in claim 1, wherein said organic solvent is one or more organic solvents that are selected from following group: methyl alcohol, ethanol, ethylene glycol, triethylene glycol, TEG, propylene glycol, Diethylene Glycol, butyleneglycol, phenylcarbinol, hexanol, propylene carbonate, tetrahydrofuran (THF), phenylmethylether, Isosorbide-5-Nitrae-dioxane, the 1-methoxy-2-propanol, phenylmethylether, dibutyl ether, phenyl ether, ethyl acetate, propyl acetate, butylacetate, ethyl propionate, ethyl ester, butyl ester, the 2-hydroxy-methyl isobutyl acid, 2-methoxyl group-1-methylethyl ester, 2-methoxy ethyl acetic ester, 2-ethoxyethyl group acetic ester, Ethylene Glycol Methyl ether acetic acid ester, ethylene glycol monoethyl ether acetate, the glycol ethyl ether propionic ester, Ethylene Glycol Methyl ether, glycol ethyl ether, diethylene glycol monomethyl ether, TC, methyl proxitol acetate, propylene glycol ethyl ether acetic ester, propylene glycol propyl ether acetic ester, the methyl proxitol propionic ester, propylene glycol ethyl ether propionic ester, propylene glycol propyl ether propionic ester, methyl proxitol, the propylene glycol ethyl ether, the propylene glycol propyl ether, propylene glycol butyl ether, the dipropylene glycol dimethyl ether, the dipropylene glycol Anaesthetie Ether, the butyleneglycol monomethyl ether, butyleneglycol list ethyl ether, the dibutylene glycol dimethyl ether, with the dibutylene glycol Anaesthetie Ether.
5. method that forms pattern, described method are used for by ink composite is contacted with the figuratum backing plate of formation on it method for imprint lithography of pattern transferring on substrate,
Wherein said ink composite comprises fluoropolymer resin, tackiness agent and organic solvent,
Described backing plate swelling ratio with respect to described ink composite after 24 hours is 0～5%,
Wherein, described ink composite comprises:
A) the described fluoropolymer resin of 5 weight parts～45 weight parts;
B) the described tackiness agent of 5 weight parts～45 weight parts; With
C) the described organic solvent of 50 weight parts～90 weight parts,
It is the viscosity sensitizing agent of 0.5 weight part～2.5 weight parts that described ink composite also comprises with respect to the described ink composite of 100 weight parts altogether,
Wherein, described fluoropolymer resin is one or more fluoropolymer resins that are selected from by the group of novolac resin, acrylic resin and their compositions of mixtures;
Described viscosity sensitizing agent is the trimeric cyanamide based cross-linker, and described trimeric cyanamide based cross-linker comprises the condensation product of condensation product, trimeric cyanamide and the formaldehyde of urea and formaldehyde, and the methylolurea alkyl oxide or the melamine methylol alkyl oxide that are obtained by alcohol.
6. the method for formation pattern as claimed in claim 5, wherein said tackiness agent is one or more tackiness agent that are selected from following group: the metal-salt of rosin ester based resin, rosin alcohol based resins and the rosin resin of the modified rosin of phenols, ethers, unmodified rosin, the polymerization by unmodified rosin, disproportionation or hydrogenation modification, the rosin resin of unsaturated fatty acids modification, unsaturated fatty acids modification.
7. the method for formation pattern as claimed in claim 5, wherein said tackiness agent is one or more tackiness agent that are selected from following group: butylation hydroxybenzene methyl ether, 2,6-di-t-butyl-4-methylolphenol, Yoshinox BHT, Tenox PG, Progallin LA, Stabilizer GA 8,2,4,5-trihydroxy-n-butyrophenone, tertiary butylated hydroquinone, the 3-amino-phenol, PAP, the 4-methoxyphenol, 2,3,5-trimethoxy phenol, 2, the 4-xylenol, 2, the 6-xylenol, poly-(4-Vinyl phenol), the 4-bromophenol, ethyl vinyl ether, poly-(methylvinylether), poly-(IVE), poly-(to hydroxyl) vinylbenzene, 1,1-two (4-hydroxy phenyl) decane, 4,4-[1-[4-[1-(1, the 4-hydroxy phenyl)-and the 1-methylethyl] phenyl] ethylidene] bis-phenol, [4, the 4-[2-hydroxy phenyl] methylene radical] two [2,6-xylenol], four (methylene radical-(3,5-di-t-butyl-4-hydroxyl hydrogenated cinnamate)) methane, 1,3,5-trimethylammonium-2,4,6-three-(3,5-di-t-butyl-4-hydroxybenzene methyl) benzene, three-(3,5-di-t-butyl-4-hydroxybenzene methyl) isocyanuric acid ester, 3-(3', the 5'-di-tert-butyl-hydroxy phenyl) propionic acid stearyl, 2,5-two (1, the 1-dimethyl propyl)-1, the 4-dihydroxy-benzene, 1,1,3-three (2-methyl)-4-hydroxyl-5-tert-butyl-phenyl butane, triethylene glycol-two-(3-tertiary butyl-4-hydroxy-5-methylbenzene methyl) propionic ester, 2,2-methylene radical two (4-methyl-6-(1-methylcyclohexyl) phenol), three (2,4-, two-tert-butyl-phenyl) phosphoric acid ester, gum resin, wood rosin, starex, the rosin of stabilization, complete all hydrogenated rosin, with partially hydrogenated rosin.
8. the method for formation pattern as claimed in claim 5, wherein said organic solvent is one or more solvents that are selected from following group: acetonitrile, methyl alcohol, ethanol, propylene carbonate, glycerine, methyl-sulphoxide, Nitromethane 99Min., dimethyl formamide, phenol, N-Methyl pyrrolidone, pyridine perfluor tributylamine, perfluorodecalin, 2-butanone, triethylene glycol and TEG.
9. the method for formation pattern as claimed in claim 5, the coating thickness of wherein said ink composite is 0.5 μ m～10 μ m.
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| KR10-2007-0129813 | 2007-12-13 | ||
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| KR1020070129813A KR101473877B1 (en) | 2007-12-13 | 2007-12-13 | Ink composition |
| KR1020080032791 | 2008-04-08 | ||
| KR10-2008-0032791 | 2008-04-08 | ||
| KR1020080032791A KR101537408B1 (en) | 2008-04-08 | 2008-04-08 | Ink composition |
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| US9169409B2 (en) | 2008-11-07 | 2015-10-27 | Lg Display Co., Ltd. | Ink composition for imprint lithography and roll printing |
| KR20110018030A (en) * | 2009-08-17 | 2011-02-23 | 주식회사 동진쎄미켐 | A ink composition |
| KR101799528B1 (en) * | 2010-05-25 | 2017-11-20 | 엘지디스플레이 주식회사 | Black matrix material for off-set printing apparatus and method of fabricating color filter substrate using the same |
| JP5884732B2 (en) * | 2010-09-10 | 2016-03-15 | 三菱化学株式会社 | Ink containing heterocyclic azo dye and dye used in the ink |
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| US20030087179A1 (en) * | 2001-05-14 | 2003-05-08 | Fuji Photo Film Co., Ltd. | Positive photoresist transfer material and method for processing surface of substrate using the transfer material |
| US6730149B2 (en) * | 2001-01-22 | 2004-05-04 | Ricoh Company Limited | Ink composition and inkjet recording method and apparatus using the ink composition |
| CN1564966A (en) * | 2001-10-31 | 2005-01-12 | 东进瑟弥侃株式会社 | Positive photoresist composition for liquid crystal device |
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| KR101324646B1 (en) * | 2006-05-08 | 2013-11-01 | 주식회사 동진쎄미켐 | Photoresist composition |
| KR101324645B1 (en) * | 2006-05-08 | 2013-11-01 | 주식회사 동진쎄미켐 | Photoresist composition |
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| US6730149B2 (en) * | 2001-01-22 | 2004-05-04 | Ricoh Company Limited | Ink composition and inkjet recording method and apparatus using the ink composition |
| US20030087179A1 (en) * | 2001-05-14 | 2003-05-08 | Fuji Photo Film Co., Ltd. | Positive photoresist transfer material and method for processing surface of substrate using the transfer material |
| CN1564966A (en) * | 2001-10-31 | 2005-01-12 | 东进瑟弥侃株式会社 | Positive photoresist composition for liquid crystal device |
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