KR20140071445A - Stripping compositions comprising mixtures of alkylamides - Google Patents
Stripping compositions comprising mixtures of alkylamides Download PDFInfo
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- KR20140071445A KR20140071445A KR1020147010936A KR20147010936A KR20140071445A KR 20140071445 A KR20140071445 A KR 20140071445A KR 1020147010936 A KR1020147010936 A KR 1020147010936A KR 20147010936 A KR20147010936 A KR 20147010936A KR 20140071445 A KR20140071445 A KR 20140071445A
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- photoresist
- stripper
- alkylamide
- present
- copper
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
- G03F7/422—Stripping or agents therefor using liquids only
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/42—Stripping or agents therefor
- G03F7/422—Stripping or agents therefor using liquids only
- G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen
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- General Physics & Mathematics (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
- Detergent Compositions (AREA)
Abstract
The present invention discloses a stripping composition having a mixture of alkylamides. The stripping composition comprises 50 to 70% by weight of N-methylformamide, 30 to 50% by weight of N, N-dimethylacetamide, and the remainder is composed of water. The stripping composition is water miscible, noncorrosive to copper or copper alloys, and has the advantage of less toxicity to humans and the environment. Due to the stripping composition comprising the two major components, the stripping solution used is easily recovered by fractional distillation, reconstituted with the original formulation, and recycled in the manufacturing process to provide advantages including cost reduction and environmental protection. Further, the present invention discloses a method for removing photoresist using a stripping composition.
Description
The present invention relates to a stripping composition containing a mixture of alkylamides, in particular an alkylamide stripping composition applied to the cleaning or removal of photoresist removal or aligning film.
The scientific and technological industries are constantly evolving and advancing, including thin-film transistor liquid crystal display (TFT-LCD) technology. Thin-film transistor liquid crystal displays are gradually replacing cathode-ray tube displays because they are advancing to the benefits of small capacity, low power consumption, low radiation, and product durability that do not take up space. In general, due to the increase in demand for displays, especially the production of thin film transistor liquid crystal displays is gradually increasing, eventually leading to the development of technology. Since the fifth, sixth, seventh and even eighth generation plants are continuously being developed, the amount invested in thin film transistor liquid crystal displays is also increasing. Therefore, future technological progress and economies of scale will be unstable.
However, due to continued advances in technology, glass substrates for thin film transistor liquid crystal displays are also becoming larger and more and more and consuming a variety of chemicals as well. In addition to the cost and resource consumption of large quantities, the manufacturing process of thin film transistor liquid crystal displays is a serious problem for the environment and creates a chemical contrary to the idea of environmental protection. Thus, the recovery of the chemical during the manufacturing process after the reaction can not only reduce the manufacturing cost, but also improve the market competitiveness and contribute significantly to environmental protection.
During the manufacturing process of a thin film transistor liquid crystal display, the amount of stripping agent (stripper) used is considerably large. Therefore, if the stripper can be recovered and recycled, it will be of considerable benefit in terms of economic profit and environmental protection. The chemicals produced during the photoresist removal process include mainly water, residual strippers, and photoresists and other post-reaction-producing materials. However, in order to retrieve strippers, the recovery systems used in conventional thin film transistor liquid crystal display plants involve the recovery of various materials using distillation techniques in view of their different boiling point characteristics; It is also necessary that the stripper be remixed according to its inherent percentage after recovery.
However, since the compositions of known strippers are quite complex and can be made of from 4 to 6 chemicals, they are very difficult to recover and after recovery the strippers are required to undergo a very complex reduction process before they can be remixed . Thus, through the recovery of known strippers in practical applications, it is difficult to achieve a reasonable economic profit, thus reducing the intent of the plant to use the stripper recovery system. In this way, there is an opportunity to reduce the cost of loss, but this will cause a considerable burden on the environment.
In addition, the components of many known strippers are very volatile and limit the bath life of such strippers, since they tend to cause excessive volatilization rates. Therefore, in storing and using such strippers, it is necessary to take special precautions for human and environmental safety.
However, due to the simple composition of the strippers available so far, they can not completely remove the photoresist from the various substrates. Very long retention times or repetitive coatings are usually required before this can be removed.
Thus, the photoresist can be completely removed, is not corrosive, has a slow rate of evaporation, is low in viscosity, and is water-miscible, so that no additional solvent is required to remove the stripper and is toxic to the human body There has been great expectations for high performance strippers that are environmentally friendly and easy to recover.
KR2010033653 discloses a dry stripper comprising 70 to 99 wt% of a mixture of N-methylformaldehyde (NMF) and N, N-dimethylacetamide (DMAC) and 0.1 to 10 wt% tetraethylene glycol. And the weight ratio of N-methyl formaldehyde to N, N-dimethylacetamide is
1: 1 to 2 (i.e., 1 or less).
The present invention provides a stripper containing a mixture of alkyl amides and comprising a mixture of N-methyl formaldehyde (NMF), N, N-dimethylacetamide (DMAC), and water to form a photoresist stripper, .
The present invention provides alkylamide strippers. As an alkylamide stripper made of N-methylformaldehyde and N, N-dimethylacetamide as two main components, it can easily strip the photoresist without damaging the copper film or the copper alloy film exposed under the photoresist, The alkylamide stripper has an advantage that can be applied to the production process of copper.
The present invention provides a stripper containing a mixture of alkylamides, which is readily recoverable through fractional distillation techniques, since the alkylamide stripper consists of only two major components with a difference in boiling point above 30 ° C at atmospheric pressure And the recovered alkylamide strippers can be remixed, reduced and recycled, thus reducing manufacturing costs and achieving environmental protection benefits.
In order to achieve the above-mentioned effect, the present invention relates to a process for the production of a composition comprising N-methylformaldehyde accounting for 50 to 70% of the total weight; N, N-dimethylacetamide, which accounts for 30 to 50% of the total weight; And water occupying the remainder of the total weight of the alkylamide stripper.
By using the practice of the present invention, at least the following effects can be achieved:
I. Since alkylamide strippers are not corrosive to copper or copper alloys, this is fairly suitable for the copper manufacturing process.
II. Since alkylamide strippers are simple in composition, have a low evaporation rate, are low in viscosity, and are water miscible, the alkylamide strippers used can easily be recovered, reducing the manufacturing cost and Environmental protection effect can be achieved.
In order that those skilled in the art will be able to understand the technical content of the present invention and thus to practice it, the disclosure, appended claims and accompanying drawings disclosed herein will be described in the preferred embodiments.
<Figs. 1 to 3>
BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 to Figure 3 are schematic diagrams of embodiments illustrating the flow process of application of an alkylamide stripper of the present invention for removal of photoresist.
<Fig. 4>
4 is an optical microscope diagram of Example 1. Fig.
5,
5 is a scanning electron microscope diagram of Example 1. Fig.
The reference symbols for the main components of the drawings are as follows: (10) a substrate; (20) a copper metal film; (30) Photoresist.
The stripper of the present invention is an alkylamide stripper comprising N-methyl formaldehyde, N, N-dimethylacetamide, and water; An alkylamide stripper of an embodiment of the present invention may be represented using the following formula:
When R and R 'are both hydrogen, it is N-dimethylformaldehyde (CAS No. 123-39-7) and R ' (CAS No. 127-19-5). In addition, the formula of the alkylamide stripper of the present invention is also C 2 H It is expressed as; (N, N- dimethyl-acetamide [CH 3 C (= O) N (CH 3) 2); 5 NO (HC (= O) NHCH 3 N- methyl-formaldehyde) and C 4 H 9 NO .
A specific example of the present invention is that the alkylamide stripper of the present invention does not contain tetraethylene glycol. Another specific example of the present invention is that the alkylamide stripper of the present invention mainly comprises N-methyl formaldehyde, which accounts for 50 to 70% of the total weight; N, N-dimethylacetamide, which accounts for 30 to 50% of the total weight; And water occupying the remainder of the total weight.
Generally, the N-methyl formaldehyde in the alkylamide stripper of the present invention accounts for 50 to 70%, preferably 55 to 65%, more preferably 58 to 62% of the total weight. N, N-dimethylacetamide in the alkylamide stripper of the present invention accounts for 30 to 50%, preferably 35 to 45%, and more preferably 38 to 42% of the total weight. The water in the alkylamide stripper of the present invention accounts for the total weight of the remainder, typically less than 5%, preferably less than 3%, more preferably less than 1%, most preferably less than 0.1%.
Another specific example of the present invention is that the alkylamide stripper of the present invention is basically water-free.
Another specific example of the present invention is that the weight ratio of N-methylformaldehyde to N, N-dimethylacetamide exceeds 1.
The stripper of the present invention can be easily produced by mixing various components at room temperature.
1 to 3, a specific flow process for applying the alkylamide stripper of the present invention to strip the
1, a
Finally, as shown in FIG. 3, the
An electronic component having a copper or copper alloy as a circuit material can be manufactured using the stripper of the present invention. In the present invention, the copper alloy having copper as the main component is a copper alloy containing 90% or more of a mass, and other elements such as Sn, Ag, Mg, Ni, Co, Cr, Ti, Mo, And the like.
A specific example of the present invention is an alkylamide stripper of the present invention, which is a photoresist stripper for removing photoresist on the surface of an electronic component. The metal circuit of the electronic component as mentioned above is composed of copper or a copper alloy.
Implementation of the alkylamide stripper of the present invention is to bring the photoresist and / or sidewall polymer (SWP) into contact with the stripper of the present invention. The actual state, such as temperature, time, etc., is determined by the nature and thickness of the photoresist material and / or sidewall polymer to be removed, and other factors such as the familiarity of those skilled in the art. Typically, photoresist stripping is carried out with a stripping composition of the present invention (for example, by spraying and dipping) at a temperature in the range of 25 to 90 占 폚 for a certain period of time ), Rinsing with water, and drying the described electronic component with an inert gas.
By way of example, photoresist materials are organic polymeric materials including electron beam photoresists, X-ray photoresists, ion beam photoresists, and the like. Practical examples of specific organic polymer materials include n-photoresist containing phenol formaldehyde resin or poly (p-vinyl phenol), photoresist containing polymethylmethacrylate, and the like.
Examples of residues (sidewall polymers) after etching, ion beam irradiation or plasma treatment can be combined with organic polymeric resins, especially metal-organic compounds and / or inorganic salts, oxides, hydroxides or alone photoresists to form membranes or compositions Residues. Conventional substrates familiar to those skilled in the art include, but are not limited to, silicon, silicon dioxide, aluminum, aluminum alloys, copper, copper alloys, etc., and the photoresist material and / Can be removed from the substrate.
The present invention also provides a method for removing a photoresist sheet from the surface of an electronic component. The method comprises contacting the electronic component having a photoresist on the surface with an alkylamide stripper of the present invention for 5 to 30 minutes at a temperature in the range of 25 to 90 DEG C to remove the photoresist. In the above-described method, the metallic circuit of the electronic component is composed of copper or a copper alloy.
Specific examples of the process of the present invention include N-methylformaldehyde, which accounts for 50 to 70% of the total weight, N, N-dimethylacetamide, which accounts for 30 to 50% of the total weight, and water, Contacting the structured alkylamide stripper with the photoresist-containing electronic component at a temperature in the range of 50 to 90 占 폚 for 5 minutes to 30 minutes to remove the photoresist.
Other specific examples of the process of the present invention include N-methyl formaldehyde, which occupies 55 to 65% of the total weight, N, N-dimethylacetamide, which occupies 35 to 45% of the total weight, Water is contacted with the photoresist-containing electronic component at a temperature in the range of 55 to 85 占 폚 for 5 to 30 minutes to remove the photoresist.
Another specific example of the process of the present invention is a process for the preparation of a composition comprising N-methylformaldehyde, which accounts for 58 to 62% of the total weight, N, N-dimethylacetamide, which accounts for 38 to 42% Is contacted with the photoresist-containing electronic component at a temperature in the range of 60 to 80 占 폚 for 5 to 30 minutes to remove the photoresist.
The alkylamide stripper of the present invention can be applied not only as a photoresist stripper for an electronic component but also for stripping or cleaning an alignment film having polyimide as a main component.
A specific example of the present invention is an alkylamide stripper of the present invention, which is provided as an orientation film stripper or an orientation film cleaner, wherein the orientation film is composed of polyimide.
Not only can the alkylamide strippers of the present invention be applied to the process of manufacturing LCD or semiconductor components, but also because alkylamide strippers are not corrosive to copper or copper alloys, they can also be applied to copper manufacturing processes to remove photoresist Or may be applied to stripping or cleaning the alignment layer.
In addition, since the alkylamide stripper is composed of only two major components, namely N-methyl formaldehyde and N, N-dimethylacetamide, whose boiling point difference exceeds 30 ° C at atmospheric pressure, Alkyl amide strippers can be easily separated from the waste liquid from the reaction and recovered through fractional distillation techniques and in order to regenerate the recovered alkyl amide strippers the alkyl amide strippers are easily rearranged following the original percentage after recovery It is possible to achieve reduction in manufacturing cost and effect of environmental protection.
The alkylamide strippers of the present invention are particularly useful and beneficial for a variety of reasons as described below. The strippers of the present invention are water miscible, noncorrosive, and are essentially non-toxic to the human body and environment. Since its evaporation rate is slower than known strippers, this can be regenerated several times and there is no need to take complex safety precautions. On the other hand, the waste of the stripped coat can be removed at any time, so it is convenient to collect and process. At the same operating temperature, the stripper of the present invention has a much better stripping effect. In addition, the stripper of the present invention is simple in composition, easy to manufacture, can mix all of its essential ingredients with its main components at room temperature, and does not require any specific safety precautions for humans or the environment.
The following is a more detailed description of the invention with examples, which are not intended to limit the application of the invention at all.
Example
A. Strippability and Corrosion Test for Copper Foil
A piece of copper foil of appropriate size (about 6 cm x 26 cm, about 2.2 g) is cut and the surface of the copper foil is cleaned using a micro-etching agent to remove the oxide on the surface. This is cleanly rinsed with deionized water, baked and dried, and then the weight (initial weight) of the copper foil is accurately measured. The copper foil is placed in a flask containing 400 g of strippers (components listed in Table 1) to test for corrosion to copper, which is heated at 80 ° C for 8 hours and the weight of the copper foil is accurately measured. The weight loss of the copper foil is measured and its corrosion rate is calculated (see Table 2).
B. Membrane-stripping effect test
The copper foil substrate is a standard specification for LCD panels, with a photoresist width of about 3 mm and a thickness of 1 to 1.5 mm. The strippers of different compositions were heated to 80 DEG C, the substrate to be tested was put in a stripper for 5 seconds, and then the substrate was immersed in water for 3 seconds, followed by air-drying using a air drier. Photoresist residues before stripping and after stripping were observed using an optical microscope and a scanning electron microscope as shown in Figs. 4 and 5, and the evaluation results are listed in Table 3.
Photoresist stripping effect:
⊚: very little photoresist residue is present, and very little photoresist backside smear is present.
A: There is a small amount of photoresistant residue, and a small amount of photoresist backside smear is present.
●: Photoresist circuit pattern There is some residual image, and there is some stain on the back of photoresist.
In optical microscope photographs, Comparative Example 1 (pure NMF) and Comparative Example 2 (pure DMAC) are poor in film-stripping effect due to the presence of a part of the photoresist circuit pattern residual image and a part of the photoresist rear surface unevenness; Comparative Example 4 is slightly better than Comparative Example 1 and Comparative Example 2 because a small amount of photoresist residue is present and a small amount of photoresist backside stain is present; The rest of the composition was able to effectively strip all of the photoresist, and it was observed that the back surface smear of the photoresist was very small.
In the photomicrographs taken with a scanning electron microscope, not all of the photoresist circuit patterns were visible, indicating that the photoresist was stripped, while still showing a small amount of photoresist residue in the photographs of Comparative Example 1 and Comparative Example 2, It was not seen in other compositions, indicating that this composition can strip the membrane well.
The results listed in Table 3 indicate that the combination of the two alkylamides from the inventive stripper provides a better synergistic stripping effect when compared to the individual alkylamide components (Comparative Example 1 and Comparative Example 2) .
C. Stripper loss test
50 g each of a stripper of Comparative Example 3 (DMAC 60% + NMF 40%) and Example 2 (DMAC 40% + NMF 60%) was placed in a 100 mL flask and heated to 80 DEG C, ≪ / RTI >
Analysis and comparison of the data listed in Table 4 reveals that the weight loss of the stripper is relatively large due to the high volatility of the DMAC during heating and after heating for 10 hours the remaining stripper in Comparative Example 3 was 63.2% , While the remaining stripper in Example 2 was 75.8% of the original amount, indicating that the former had a 12.6% greater loss. Since the stripper is mostly used in the heated state (50 DEG C to 90 DEG C), reducing the loss of the stripper during the heating process is beneficial to both environmental protection and improvement of the working time.
Using the stripper of the present invention, due to the high content (occupying 50 to 70% by weight of the total weight) of NMF, the overall steam loss rate is relatively low, so that the stripper has a much longer continuous working time, Of strippers are included in the waste gas in the form of wastewater and vapor.
D. Ignition Test
The stripper needs to be heated to a specific temperature range (60 DEG C to 90 DEG C) before achieving the required stripping effect. However, at these operating temperatures, safety becomes an important consideration. DMAC has a flash point of 63 ° C, whereas NMF has a flash point of 119 ° C. The flash point was tested using the closed cup ASTM D93 method, the flash point of Comparative Example 3 was 80.5 ° C, and the flash point of Example 2 was 88.5 ° C. The flash point of the stripper of the present invention is higher than the flash point of a known stripper (Comparative Example 3), which enhances the safety of factory operations.
The above-mentioned embodiments illustrate the features of the present invention and do not limit the scope of the present invention, but those skilled in the art will understand the contents of the present invention and accordingly, Therefore, all other equivalent modifications or alterations that are carried out without departing from the spirit of the invention disclosed in the specification are to be included in the scope of the appended claims.
Claims (10)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110285604.1A CN103019049B (en) | 2011-09-23 | 2011-09-23 | Stripping agent containing alkylamide mixture |
| CN201110285604.1 | 2011-09-23 | ||
| PCT/US2012/056872 WO2013044210A2 (en) | 2011-09-23 | 2012-09-24 | Stripping compositions having mixtures of alkylamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20140071445A true KR20140071445A (en) | 2014-06-11 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147010936A KR20140071445A (en) | 2011-09-23 | 2012-09-24 | Stripping compositions comprising mixtures of alkylamides |
Country Status (4)
| Country | Link |
|---|---|
| KR (1) | KR20140071445A (en) |
| CN (1) | CN103019049B (en) |
| TW (1) | TWI567510B (en) |
| WO (1) | WO2013044210A2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105524627B (en) * | 2015-12-03 | 2017-12-01 | 阜阳欣奕华材料科技有限公司 | A kind of purification process and purification devices of liquid crystal aligning liquid waste liquid |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20090072546A (en) * | 2007-12-28 | 2009-07-02 | 삼성전자주식회사 | Composition for removing photoresist and method of manufacturing array substrate using the same |
| KR101374686B1 (en) * | 2008-09-22 | 2014-03-18 | 에스케이종합화학 주식회사 | Stripper Composition for removing photoresist |
| KR101579846B1 (en) * | 2008-12-24 | 2015-12-24 | 주식회사 이엔에프테크놀로지 | Composition for removing a photoresist pattern and method of forming a metal pattern using the composition |
| KR20110007828A (en) * | 2009-07-17 | 2011-01-25 | 동우 화인켐 주식회사 | Stripper composition for copper or copper alloy interconnection |
| CN101750917A (en) * | 2009-09-25 | 2010-06-23 | 株式会社Lg化学 | Remover composition for photoresist and method for removing photoresist |
-
2011
- 2011-09-23 CN CN201110285604.1A patent/CN103019049B/en active Active
-
2012
- 2012-09-24 TW TW101134879A patent/TWI567510B/en active
- 2012-09-24 KR KR1020147010936A patent/KR20140071445A/en not_active Application Discontinuation
- 2012-09-24 WO PCT/US2012/056872 patent/WO2013044210A2/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| WO2013044210A3 (en) | 2013-07-04 |
| CN103019049B (en) | 2014-10-08 |
| TW201317721A (en) | 2013-05-01 |
| CN103019049A (en) | 2013-04-03 |
| WO2013044210A2 (en) | 2013-03-28 |
| TWI567510B (en) | 2017-01-21 |
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