WO2014002151A1 - Resist stripping agent - Google Patents
Resist stripping agent Download PDFInfo
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- WO2014002151A1 WO2014002151A1 PCT/JP2012/006286 JP2012006286W WO2014002151A1 WO 2014002151 A1 WO2014002151 A1 WO 2014002151A1 JP 2012006286 W JP2012006286 W JP 2012006286W WO 2014002151 A1 WO2014002151 A1 WO 2014002151A1
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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
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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
Definitions
- the present invention relates to a resist remover used for removing a resist film after an etching operation in a photolithography process for forming a metal wiring pattern on a silicon substrate or a glass substrate.
- amine-based resist stripping agents have been used as stripping agents for resist films made of novolak resin.
- this amine-based resist remover for example, a multi-component in which a water-soluble organic solvent such as dimethyl sulfoxide and water are added to amines such as monoethanolamine, N-methylaminoethanol, N-methyl-2-pyrrolidone, etc.
- resist strippers There are known resist strippers. (For example, refer to Patent Document 1.)
- amine-based resist strippers cut the crosslinking points between the novolak resin and the photosensitizer and form salts with the photosensitizer and resin. As a result, the resist film is solubilized and peeled from the substrate.
- these multi-component amine-based resist removers have many low-boiling components and have different vapor pressures. Therefore, there is a problem that the composition varies during use due to the difference in evaporation amount of each component during use, and the peeling performance is lowered. Further, since the amount of the resist stripped material dissolved in the resist stripper increases when used repeatedly, there is a problem that the stripping performance is deteriorated due to the influence of the resist stripped material. Furthermore, the amine-based resist stripper is highly corrosive to copper wiring, and may cause disconnection or the like when the wiring pattern is further refined.
- resist strippers other than amine-based resist strippers for example, resist strippers mainly composed of ethylene carbonate and propylene carbonate and resist strippers mainly composed of ethylene carbonate and ⁇ -butyrolactone are known.
- resist strippers it is also known to reuse a resist stripper after decomposing only the resist strip by blowing ozone-containing gas into a solution in which the resist strip after the resist strip is dissolved.
- Patent Document 2 and Patent Document 3. A resist remover in which cyclohexanone and butyl acetate are mixed is also known.
- Patent Document 4 A resist remover in which cyclohexanone and butyl acetate are mixed is also known.
- a resist stripper is required to have excellent stripping performance, no corrosion on metal wiring, particularly copper wiring, high flash point and high safety in consideration of work under heating.
- a rinsing process is performed following the resist stripping process after etching.
- the resist remover adhering to the substrate is washed away with pure water.
- the resist strips dissolved in the resist stripper are deposited on the substrate surface, or fine particles of the resist strips dispersed in the resist stripper are reattached to the substrate surface. There is a problem of doing.
- the present invention has been made to solve such problems, and has an excellent resist stripping performance and an object of providing a resist stripper that does not deposit or reattach a resist stripped substance on a substrate during rinsing with pure water. And Another object of the present invention is to provide a resist remover that is not corrosive to metal wiring, particularly copper wiring. Furthermore, it aims at providing the resist stripper which can be reused.
- the present inventors have selected from ethylene carbonate, propylene carbonate, ⁇ -butyrolactone and cyclopentanone that have been used as resist strippers. It has been found that by adding glycerol carbonate to one or more of the above, the resist stripped material is not deposited or reattached to the substrate during rinsing with pure water.
- the present invention has been made on the basis of such findings, and at the time of pure water rinsing in which glycerol carbonate is added to one or more selected from ethylene carbonate, propylene carbonate, ⁇ -butyrolactone and cyclopentanone. It is an object of the present invention to provide a resist remover that does not deposit or reattach a resist exfoliation product to a substrate.
- a first embodiment of the resist stripper of the present invention comprises (A) one or more selected from 50 to 99% by mass selected from ethylene carbonate, propylene carbonate, ⁇ -butyrolactone and cyclopentanone, and (B) glycerol carbonate. 1 to 50% by mass.
- one or more compounds selected from ethylene carbonate, propylene carbonate, ⁇ -butyrolactone and cyclopentanone may be referred to as “component (A)”, and glycerol carbonate may be referred to as “component (B)”.
- a second embodiment of the resist stripper of the present invention is characterized in that, in the first embodiment, the component (A) is one or more selected from ethylene carbonate and propylene carbonate.
- the third embodiment of the resist stripper of the present invention is the same as the first embodiment except that 20 to 80% by mass of ethylene carbonate, 5 to 30% by mass of propylene carbonate, and (B) 5 to 50 of glycerol carbonate. It consists of mass%.
- a fourth embodiment of the resist stripper of the present invention in the first embodiment, 55 to 75% by mass of ethylene carbonate, 5 to 25% by mass of propylene carbonate, and 10 to 30 of (B) glycerol carbonate. It consists of mass%.
- the fifth to eighth embodiments of the resist stripper of the present invention include 30 parts by mass or less of water with respect to 100 parts by mass of any one of the first to fourth embodiments.
- the ninth and tenth embodiments of the resist stripper of the present invention are characterized in that, in the first to eighth embodiments, the viscosity at 60 ° C. is 10 cP or less.
- An eleventh embodiment of the resist stripper of the present invention is characterized in that the flash point is 100 ° C. or higher in the first to tenth embodiments.
- the resist stripper of the present invention is excellent in stripping performance. Further, even if rinsing with pure water directly after the resist is peeled off, the resist peeled material is not deposited on the surface of the substrate and is not reattached. Furthermore, there is no corrosive action on copper wiring and aluminum wiring. Moreover, since a low boiling point component is not included, the component composition does not change during use. Therefore, it is safe even when the resist film is peeled off by heating the resist stripping agent.
- FIG. 4B is a side view schematically showing the sample shown in FIG. 4A.
- room temperature in the following description refers to this temperature range.
- the resist stripper of this embodiment has a five-membered ring structure in the molecular structure of both the component (A) and the component (B).
- One of the carbon atoms constituting this five-membered ring has a common molecular structure constituting a carbonyl group. Therefore, compatibility is good and it can mix easily. Moreover, the solubility with respect to a resist film, especially the resist film which consists of novolak resin is high, and it is excellent in resist stripping performance.
- Each component (A) is known as a resist remover.
- the component (B) acts to prevent the resist stripped material from being deposited and reattached.
- the blending ratio of the component (A) and the component (B) is 50 to 99% by mass of the component (A) and 1 to 50% by mass of the component (B), preferably 50 to 95% by mass of the component (A), ( B) 5 to 50% by mass of component, more preferably 70 to 90% by mass of component (A) and 10 to 30% by mass of component (B).
- the component (B) has a higher viscosity than the component (A). Therefore, when a low-viscosity resist stripper is required for work, it is desirable to appropriately increase the proportion of component (A).
- the proportion of the component (A) when the proportion of the component (A) is less than 50% by mass, the peeling action on the resist film is lowered, and the proportion of the component (B) is excessively increased to increase the viscosity. As a result, a problem arises in workability such as an increase in processing temperature. Further, when the proportion of the component (A) exceeds 99% by mass, the proportion of the component (B) becomes too small, and when the resist film on the substrate is peeled off, the resist stripped material is formed on the substrate surface when directly rinsed with pure water. There is a possibility of precipitation or redeposition.
- the resist remover in which the component (B) is added to the component (A) has a higher affinity for the resist because the contact angle to the substrate is smaller than the resist remover of the component (A) alone. It is speculated that This is considered to be the reason why it is difficult to deposit the resist strip when rinsed with pure water.
- the resist remover of the second embodiment uses ethylene carbonate as the component (A).
- the component (A) of the first embodiment is only ethylene carbonate, and the preferred ratio of the (A) component and the (B) component, the more preferred ratio is the same as that of the first embodiment. is there.
- the amount of ethylene carbonate is 80% by mass or more, the ethylene carbonate is not completely dissolved and precipitates at room temperature. Therefore, in this case, it is necessary to heat and use it up to a temperature at which ethylene carbonate dissolves.
- the third and fourth embodiments use ethylene carbonate and propylene carbonate at a predetermined ratio as the component (A) in the first embodiment.
- the content of ethylene carbonate in the resist stripper of this embodiment is 20 to 80% by mass, more preferably 55 to 75% by mass, and the content of propylene carbonate is 5 to 30% by mass, more preferably 5 to 5%. 25% by mass.
- the ratio of the total amount of ethylene carbonate and propylene carbonate as the component (A) and the component (B) is the same as in the first embodiment.
- the melting point becomes 15 ° C. or less, and it becomes liquid at room temperature, and the workability can be improved.
- the preferred ratio of the component (A) to the component (B) and the reason thereof are the same as those described for the first embodiment.
- the amount of water added to the resist remover of this embodiment is 30 parts by mass or less, more preferably 10 to 25 parts by mass with respect to 100 parts by mass of the entire resist remover. If the amount of water added exceeds 30 parts by mass, sufficient resist stripping performance may not be obtained. If it is less than 10 parts by mass, the degree of increase in flash point will be small.
- the ninth and tenth embodiments are characterized in that the viscosity of the resist stripper at 60 ° C. is 10 cP or less, and preferably 5 cP. Since the (B) component of the present invention has a high viscosity, when the blending amount of the (B) component is large, the viscosity becomes high, which may hinder the work. In such a case, it is desirable to perform the peeling operation by heating to lower the viscosity to the above range.
- this invention is not limited to the above embodiment. It is also possible to add other additives such as a small amount of a water-soluble organic solvent as long as the effects of the present invention are not impaired.
- each component of the present invention has a five-membered basic structure, and thus is highly resistant to ozone oxidation. For this reason, ozone-containing gas is blown into a used release agent in which a resist is dissolved to decompose and remove impurities for reuse.
- the resist stripper of the present invention does not use an amine compound, it does not corrode copper wiring or aluminum wiring.
- a glass substrate (manufactured by CORNING, trade name: Eagle 2000, 10 mm ⁇ 50 mm, thickness 0.7 mm) is immersed for 60 seconds in 100 mL of a resist solution having various concentrations to be evaluated heated to 60 ° C. with a hot stirrer, and then Rinse by immersing in pure water (hydrostatic water) at room temperature for 60 seconds, and rinsing and drying with nitrogen gas.
- the substrate surface was observed with a 10-fold optical microscope (trade name: Industrial Inspection Microscope MX51, manufactured by Olympus Corporation), and the presence or absence of deposits or deposits on the substrate surface was confirmed.
- Samples (resist removers) 1 to 33 the allowable resist concentration was evaluated as follows.
- Resist tolerance 1.0 mass% or more A 0.3 mass% or more and less than 1.0 mass% ... B 0.1 mass% or more and less than 0.3 mass% ... C Less than 0.1% by mass D
- a resist stripper having an allowable resist concentration of about 0.1% by mass or more is practical because no residue is generated during pure water rinsing.
- viscosity of samples (resist stripping agents) 1 to 33 was evaluated as follows. [Evaluation of viscosity] A sample to be evaluated (resist stripper) was heated to 60 ° C., and the viscosity was measured using a rotary viscometer (trade name: Viscomate Model VM-10A [cylinder diameter: 3.5 mm] manufactured by CBC). viscosity: Less than 5 cP ... A 5 cP to less than 10 cP... B 10cP or more ... C
- the resist stripper of the embodiment has a high resist allowable concentration. Therefore, in the resist stripper of the embodiment, generation of a residue during rinsing with pure water is extremely suppressed. From Table 3, it can be seen that the resist stripper of the embodiment to which water is added has a high flash point, and in particular, Sample 37 and Sample 38 containing water in a predetermined ratio or more have no flammability. Therefore, the resist stripper of the embodiment to which water is added can be made more excellent in safety. In addition, it can be seen that the resist stripper of the embodiment contains EC, PC, and GC in the ratio of the present invention, and therefore has a low viscosity at 60 ° C. and excellent workability.
- FIG. 3A is a plan view of a sample used in the simulation test 2.
- FIG. 3B is a side view of the same.
- a novolac resin-based positive resist (trade name / ZPP-1800-15 (Nippon Zeon Co., Ltd.) is applied to a glass substrate 1 (trade name / Eagle 2000 (manufactured by CORNING)) of 30 mm ⁇ 50 mm ⁇ 0.7 mm. Manufactured)) was applied by slitting with a film thickness of 2 ⁇ m, and this was prebaked (110 ° C.
- a polyimide tape 3 (trade name / API-114 (manufactured by Chuko Flow Co., Ltd.)) having a width of 19.0 mm and a thickness of 0.06 mm is applied to the center of the resist coating portion 2 of the glass substrate 1 in the length direction.
- a sample was attached.
- a tape is cut off at a depth reaching the surface of the glass substrate 1 in the length direction toward one side of the pasted polyimide tape 3 in the width direction, and the tape at the outer portion is removed, as shown in FIGS. 3A and 3B.
- the cutting line (between the reference numerals 3 and 2) was used as a start line for the penetration distance.
- FIG. 4A is a plan view of the evaluation sample after immersion
- FIG. 4B is a side view thereof. After the drying treatment, the polyimide tape 3 of the evaluation sample as shown in FIGS.
- a sample (resist stripper) 44 containing EC: PC: GC at 65:15:20 and a sample (resist stripper) containing EC: PC: GC: water at a ratio of 50: 15: 15: 20 ) 45 is less corrosive to Cu and Al than general amine release agents.
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Abstract
Description
しかし、これらの多成分のアミン系のレジスト剥離剤の成分には、低沸点成分が多く、かつ各成分の蒸気圧がそれぞれ異なる。そのため使用中の各成分の蒸発量が異なることで、使用中に組成が変動し、剥離性能が低下するという問題がある。また、繰り返し使用しているとレジスト剥離剤中のレジスト剥離物の溶解量が増加するためこのレジスト剥離物の影響により剥離性能が低下するという問題がある。さらに、アミン系のレジスト剥離剤は、銅配線に対する腐食性が大きく、配線パターンのファイン化がさらに進んだ場合に断線等の原因となるおそれもある。 These amine-based resist strippers cut the crosslinking points between the novolak resin and the photosensitizer and form salts with the photosensitizer and resin. As a result, the resist film is solubilized and peeled from the substrate.
However, these multi-component amine-based resist removers have many low-boiling components and have different vapor pressures. Therefore, there is a problem that the composition varies during use due to the difference in evaporation amount of each component during use, and the peeling performance is lowered. Further, since the amount of the resist stripped material dissolved in the resist stripper increases when used repeatedly, there is a problem that the stripping performance is deteriorated due to the influence of the resist stripped material. Furthermore, the amine-based resist stripper is highly corrosive to copper wiring, and may cause disconnection or the like when the wiring pattern is further refined.
また、シクロヘキサノンと酢酸ブチルとを混合したレジスト剥離剤も知られている。(例えば、特許文献4参照。) As resist strippers other than amine-based resist strippers, for example, resist strippers mainly composed of ethylene carbonate and propylene carbonate and resist strippers mainly composed of ethylene carbonate and γ-butyrolactone are known. In these resist strippers, it is also known to reuse a resist stripper after decomposing only the resist strip by blowing ozone-containing gas into a solution in which the resist strip after the resist strip is dissolved. (For example, see
A resist remover in which cyclohexanone and butyl acetate are mixed is also known. (For example, see Patent Document 4)
また、フォトリソグラフィ工程では、エッチング後のレジスト剥離工程に続いてリンス工程が行われる。リンス工程では、基板に付着したレジスト剥離剤を純水で洗浄除去する。この純水によるリンス工程で、レジスト剥離剤中に溶解しているレジスト剥離物が基板表面に析出したり、レジスト剥離剤中に分散しているレジスト剥離物の微粒子が基板表面に再付着したりするという問題がある。
このようなレジスト剥離物の基板表面への析出や再付着を防ぐには、高圧の純水シャワーなどにより基板に物理的な力を加えながら長時間リンスを行う方法や、純水によるリンス工程に先立って水溶性の有機溶剤によるリンスを行う方法などの方法がとられる。しかし、いずれの方法も生産性や作業性を損なうという問題がある。特に、後者の方法では、リンスに用いた純水の処理のほかにリンスに用いた水溶性の有機溶剤の処理の問題も生じる。 In general, a resist stripper is required to have excellent stripping performance, no corrosion on metal wiring, particularly copper wiring, high flash point and high safety in consideration of work under heating.
In the photolithography process, a rinsing process is performed following the resist stripping process after etching. In the rinsing step, the resist remover adhering to the substrate is washed away with pure water. In this rinsing process with pure water, the resist strips dissolved in the resist stripper are deposited on the substrate surface, or fine particles of the resist strips dispersed in the resist stripper are reattached to the substrate surface. There is a problem of doing.
In order to prevent deposition and re-deposition of such resist strips on the substrate surface, a method of rinsing for a long time while applying physical force to the substrate by a high pressure pure water shower or the like, or a rinsing process with pure water A method such as a method of rinsing with a water-soluble organic solvent is employed in advance. However, each method has a problem that productivity and workability are impaired. In particular, in the latter method, in addition to the treatment of pure water used for rinsing, there is a problem of treatment of the water-soluble organic solvent used for rinsing.
本発明の他の目的は、このレジスト剥離剤において、金属配線、特に銅配線に対する腐食性がないレジスト剥離剤の提供を目的とする。さらに、リユースが可能なレジスト剥離剤の提供を目的とする。 The present invention has been made to solve such problems, and has an excellent resist stripping performance and an object of providing a resist stripper that does not deposit or reattach a resist stripped substance on a substrate during rinsing with pure water. And
Another object of the present invention is to provide a resist remover that is not corrosive to metal wiring, particularly copper wiring. Furthermore, it aims at providing the resist stripper which can be reused.
本発明は、かかる知見に基づいてなされたもので、炭酸エチレン、炭酸プロピレン、γ-ブチロラクトン及びシクロペンタノンから選ばれる1種以上に、炭酸グリセロールを添加してなる、純水リンスの際に、レジスト剥離物の基板への析出や再付着のないレジスト剥離剤を提供しようとするものである。 As a result of diligent research to solve the above problems in conventional resist strippers, the present inventors have selected from ethylene carbonate, propylene carbonate, γ-butyrolactone and cyclopentanone that have been used as resist strippers. It has been found that by adding glycerol carbonate to one or more of the above, the resist stripped material is not deposited or reattached to the substrate during rinsing with pure water.
The present invention has been made on the basis of such findings, and at the time of pure water rinsing in which glycerol carbonate is added to one or more selected from ethylene carbonate, propylene carbonate, γ-butyrolactone and cyclopentanone. It is an object of the present invention to provide a resist remover that does not deposit or reattach a resist exfoliation product to a substrate.
なお、本明細書において、炭酸エチレン、炭酸プロピレン、γ-ブチロラクトン及びシクロペンタノンから選ばれる1種以上の化合物を、「(A)成分」、炭酸グリセロールを「(B)成分」ということがある。
本発明のレジスト剥離剤の第2の実施形態は、第1の実施形態において、(A)成分が炭酸エチレン及び炭酸プロピレンから選ばれる1種以上であることを特徴とする。
本発明のレジスト剥離剤の第3の実施形態は、第1の実施形態において、炭酸エチレンの20~80質量%と、炭酸プロピレンの5~30質量%と、(B)炭酸グリセロールの5~50質量%とからなることを特徴とする。
本発明のレジスト剥離剤の第4の実施形態は、第1の実施形態において、炭酸エチレンの55~75質量%と、炭酸プロピレンの5~25質量%と、(B)炭酸グリセロールの10~30質量%とからなることを特徴とする。
本発明のレジスト剥離剤の第5乃至第8の実施形態は、第1乃至第4のいずれかの実施形態の100質量部に対して水を30質量部以下含むことを特徴とする。
本発明のレジスト剥離剤の第9及び第10の実施形態は、第1乃至第8の実施形態において60℃における粘度が10cP以下であることを特徴とする。
本発明のレジスト剥離剤の第11の実施形態は、第1乃至第10の実施形態において引火点が100℃以上であることを特徴とする。 A first embodiment of the resist stripper of the present invention comprises (A) one or more selected from 50 to 99% by mass selected from ethylene carbonate, propylene carbonate, γ-butyrolactone and cyclopentanone, and (B) glycerol carbonate. 1 to 50% by mass.
In the present specification, one or more compounds selected from ethylene carbonate, propylene carbonate, γ-butyrolactone and cyclopentanone may be referred to as “component (A)”, and glycerol carbonate may be referred to as “component (B)”. .
A second embodiment of the resist stripper of the present invention is characterized in that, in the first embodiment, the component (A) is one or more selected from ethylene carbonate and propylene carbonate.
The third embodiment of the resist stripper of the present invention is the same as the first embodiment except that 20 to 80% by mass of ethylene carbonate, 5 to 30% by mass of propylene carbonate, and (B) 5 to 50 of glycerol carbonate. It consists of mass%.
In a fourth embodiment of the resist stripper of the present invention, in the first embodiment, 55 to 75% by mass of ethylene carbonate, 5 to 25% by mass of propylene carbonate, and 10 to 30 of (B) glycerol carbonate. It consists of mass%.
The fifth to eighth embodiments of the resist stripper of the present invention include 30 parts by mass or less of water with respect to 100 parts by mass of any one of the first to fourth embodiments.
The ninth and tenth embodiments of the resist stripper of the present invention are characterized in that, in the first to eighth embodiments, the viscosity at 60 ° C. is 10 cP or less.
An eleventh embodiment of the resist stripper of the present invention is characterized in that the flash point is 100 ° C. or higher in the first to tenth embodiments.
さらに、銅配線やアルミ配線に対する腐食作用がない。また、低沸点成分を含まないので使用中に成分組成が変化することがないので、レジスト剥離剤を加熱してレジスト被膜の剥離を行う場合でも安全である。 The resist stripper of the present invention is excellent in stripping performance. Further, even if rinsing with pure water directly after the resist is peeled off, the resist peeled material is not deposited on the surface of the substrate and is not reattached.
Furthermore, there is no corrosive action on copper wiring and aluminum wiring. Moreover, since a low boiling point component is not included, the component composition does not change during use. Therefore, it is safe even when the resist film is peeled off by heating the resist stripping agent.
本発明の第1の実施形態は、(A)炭酸エチレン、炭酸プロピレン、γ-ブチロラクトン及びシクロペンタノンから選ばれる1種以上の50~99質量%と、(B)炭酸グリセロールの1~50質量%とからなる。 (First embodiment)
In the first embodiment of the present invention, (A) 50 to 99% by mass of one or more selected from ethylene carbonate, propylene carbonate, γ-butyrolactone and cyclopentanone, and (B) 1 to 50% by mass of glycerol carbonate %.
なお、例えば工場のクリーンルームにおける通常の作業環境温度は22~27℃であるので、以下の説明における「室温」は、この温度範囲をいう。
For example, since the normal working environment temperature in a clean room of a factory is 22 to 27 ° C., “room temperature” in the following description refers to this temperature range.
(A)成分は、それぞれレジスト剥離剤として知られているものである。しかし、(A)成分だけでは、基板のレジスト被膜を剥離した後、直接純水でリンスしたときに溶解しているレジスト剥離物が基板表面に析出したり、再付着したりするおそれがある。
(B)成分は、このレジスト剥離物の析出や再付着を防止する作用をする。
(A)成分と(B)成分の配合割合は、(A)成分50~99質量%、(B)成分1~50質量%であるが、好ましくは(A)成分50~95質量%、(B)成分5~50質量%、より好ましくは、(A)成分70~90質量%、(B)成分10~30質量%、である。
表1に示されるように、(B)成分は(A)成分と比較して粘度が高い。そのため、作業上低粘度のレジスト剥離剤を必要とする場合には、(A)成分の割合を適宜多くすることが望ましい。 The resist stripper of this embodiment has a five-membered ring structure in the molecular structure of both the component (A) and the component (B). One of the carbon atoms constituting this five-membered ring has a common molecular structure constituting a carbonyl group. Therefore, compatibility is good and it can mix easily. Moreover, the solubility with respect to a resist film, especially the resist film which consists of novolak resin is high, and it is excellent in resist stripping performance.
Each component (A) is known as a resist remover. However, with the component (A) alone, there is a possibility that the resist peeled material dissolved when directly rinsing with pure water is peeled off or reattached to the substrate surface after the resist film on the substrate is peeled off.
The component (B) acts to prevent the resist stripped material from being deposited and reattached.
The blending ratio of the component (A) and the component (B) is 50 to 99% by mass of the component (A) and 1 to 50% by mass of the component (B), preferably 50 to 95% by mass of the component (A), ( B) 5 to 50% by mass of component, more preferably 70 to 90% by mass of component (A) and 10 to 30% by mass of component (B).
As shown in Table 1, the component (B) has a higher viscosity than the component (A). Therefore, when a low-viscosity resist stripper is required for work, it is desirable to appropriately increase the proportion of component (A).
第2の実施形態のレジスト剥離剤は、(A)成分として炭酸エチレンを用いるものである。この実施形態は、第1の実施形態の(A)成分が炭酸エチレンとされているだけで、(A)成分と(B)成分の好ましい割合、より好ましい割合は第1の実施形態と同じである。 (Second Embodiment)
The resist remover of the second embodiment uses ethylene carbonate as the component (A). In this embodiment, the component (A) of the first embodiment is only ethylene carbonate, and the preferred ratio of the (A) component and the (B) component, the more preferred ratio is the same as that of the first embodiment. is there.
第3及び第4の実施形態は、第1の実施形態において、(A)成分として炭酸エチレン及び炭酸プロピレンを所定の割合で用いるものである。
この実施形態のレジスト剥離剤の炭酸エチレンの含有割合は、20~80質量%、より好ましくは55~75質量%であり、炭酸プロピレンの含有割合は、5~30質量%、より好ましくは5~25質量%である。(A)成分としての炭酸エチレンと炭酸プロピレンの合計量と(B)成分との割合は、第1の実施形態と同じである。 (Third and fourth embodiments)
The third and fourth embodiments use ethylene carbonate and propylene carbonate at a predetermined ratio as the component (A) in the first embodiment.
The content of ethylene carbonate in the resist stripper of this embodiment is 20 to 80% by mass, more preferably 55 to 75% by mass, and the content of propylene carbonate is 5 to 30% by mass, more preferably 5 to 5%. 25% by mass. The ratio of the total amount of ethylene carbonate and propylene carbonate as the component (A) and the component (B) is the same as in the first embodiment.
第5乃至第8の実施形態は、第1乃至第4のいずれかの実施形態のレジスト剥離剤100質量部に対して水を30質量部以下添加したものである。
第1乃至第4の実施形態のレジスト剥離剤は、低沸点成分を含まないため、常温や比較的低い温度に加温しての作業には、格別の、火災に対する配慮は不要である。しかし、より高い温度での剥離作業の際には、蒸気の発生に対する配慮が必要である。
第5乃至第8の実施形態は、第1乃至第4の実施形態のレジスト剥離剤に、さらに水を添加することにより引火点を高くし、加熱作業の際の安全性をより高くしたものである。 (Fifth to eighth embodiments)
In the fifth to eighth embodiments, 30 parts by mass or less of water is added to 100 parts by mass of the resist stripper of any one of the first to fourth embodiments.
Since the resist remover of the first to fourth embodiments does not contain a low-boiling component, special consideration for fire is not necessary for the operation of heating to room temperature or a relatively low temperature. However, consideration must be given to the generation of steam during the stripping operation at a higher temperature.
In the fifth to eighth embodiments, the flash point is increased by further adding water to the resist remover of the first to fourth embodiments, and the safety during the heating operation is further increased. is there.
水の添加量が30質量部を超えると、十分なレジスト剥離性能を得られないおそれがあり、10質量部より少ないと、引火点の上昇の程度が小さいものとなる。 The amount of water added to the resist remover of this embodiment is 30 parts by mass or less, more preferably 10 to 25 parts by mass with respect to 100 parts by mass of the entire resist remover.
If the amount of water added exceeds 30 parts by mass, sufficient resist stripping performance may not be obtained. If it is less than 10 parts by mass, the degree of increase in flash point will be small.
第9及び第10の実施形態は、レジスト剥離剤の60℃における粘度が、10cP以下であることを特徴としており、好ましくは5cPである。
本発明の(B)成分は粘度が高いので、(B)成分の配合量が多い場合には、粘度が高くなり、作業に支障をきたす場合が考えられる。このような場合には、加熱して粘度を上記範囲にまで低くして剥離作業を行うことが望ましい。 (Ninth and Tenth Embodiments)
The ninth and tenth embodiments are characterized in that the viscosity of the resist stripper at 60 ° C. is 10 cP or less, and preferably 5 cP.
Since the (B) component of the present invention has a high viscosity, when the blending amount of the (B) component is large, the viscosity becomes high, which may hinder the work. In such a case, it is desirable to perform the peeling operation by heating to lower the viscosity to the above range.
なお、以下の記号は次の物質を示している。
EC:炭酸エチレン
PC:炭酸プロピレン
GC:炭酸グリセロール
GBL:γ-ブチロラクトン
CP:シクロペンタノン
MEA:モノエタノールアミン
DMSO:ジメチルスルホキシド
PFA:四フッ化エチレン-パーフルオロアルコキシエチレン共重合体 Next, examples of the present invention will be described.
The following symbols indicate the following substances.
EC: ethylene carbonate PC: propylene carbonate GC: glycerol carbonate GBL: γ-butyrolactone CP: cyclopentanone MEA: monoethanolamine DMSO: dimethyl sulfoxide PFA: tetrafluoroethylene-perfluoroalkoxyethylene copolymer
模擬実験1(レジスト許容濃度の評価)
表2の混合割合で調整した試料(レジスト剥離剤)について、以下のように剥離レジスト溶解剥離剤(以下、「レジスト溶解液」という。)を調整したのち、レジスト許容濃度の評価を行った。レジスト許容濃度の評価において、リンス後の基板表面に図1に示す光学顕微鏡写真のように析出物又は付着物が生じない最大の濃度を測定し、この濃度をレジスト許容濃度とした。析出物又は付着物が生じた場合の光学顕微鏡写真を図2に示す。 (Evaluation of resist remover 1)
Mock experiment 1 (Evaluation of allowable resist density)
About the sample (resist stripping agent) adjusted with the mixing ratio of Table 2, after adjusting the stripping resist dissolving stripping agent (hereinafter referred to as “resist dissolving solution”), the resist allowable concentration was evaluated. In the evaluation of the resist allowable concentration, the maximum concentration at which no precipitate or deposit was generated as shown in the optical micrograph shown in FIG. 1 was measured on the substrate surface after rinsing, and this concentration was defined as the resist allowable concentration. An optical micrograph in the case where precipitates or deposits are generated is shown in FIG.
ガラスシャーレ(商品名/フラットシャーレ(アズワン(株)社製))にノボラック樹脂系ポジ型レジスト(商品名/ZPP-1800-15(日本ゼオン(株)社製))を1mL滴下し、薄膜としたものをプリベーク110℃で5分、ポストベーク130℃で5分行い硬化させた。
評価対象の試料(レジスト剥離剤)に、硬化させたノボラック樹脂系ポジ型レジストを溶解させ、各種濃度のレジスト溶解液を調整した。
[レジスト許容濃度の評価]
ホットスターラーで60℃に加温した評価対象の各種濃度のレジスト溶解液100mLにガラス基板(CORNING社製、商品名:イーグル2000、10mm×50mm、厚さ0.7mm)を60秒間浸漬し、次いで常温の純水(静水)中に60秒間浸漬してリンスし、リンス後窒素ガスで乾燥させた。10倍の光学顕微鏡(オリンパス社製、商品名:工業用検査顕微鏡MX51)で基板表面を観察し、基板表面の析出物又は付着物の有無を確認した。
試料(レジスト剥離剤)1~33について、以下のようにレジスト許容濃度を評価した。 [Preparation of resist solution]
1 mL of a novolak resin-based positive resist (trade name / ZPP-1800-15 (manufactured by ZEON Corporation)) was dropped on a glass petri dish (trade name / flat petri dish (manufactured by ASONE Co., Ltd.)) This was cured by pre-baking at 110 ° C. for 5 minutes and post-baking at 130 ° C. for 5 minutes.
The cured novolac resin-based positive resist was dissolved in the sample to be evaluated (resist stripper) to prepare resist solutions of various concentrations.
[Evaluation of allowable resist density]
A glass substrate (manufactured by CORNING, trade name:
With respect to Samples (resist removers) 1 to 33, the allowable resist concentration was evaluated as follows.
レジスト許容濃度:
1.0質量%以上 …A
0.3質量%以上1.0質量%未満 …B
0.1質量%以上0.3質量%未満 …C
0.1質量%未満 …D
なお、工業的には、レジスト許容濃度が0.1質量%程度以上のレジスト剥離剤であれば純水リンスの際に残渣物が発生することがなく実用的である。 [Evaluation]
Resist tolerance:
1.0 mass% or more A
0.3 mass% or more and less than 1.0 mass% ... B
0.1 mass% or more and less than 0.3 mass% ... C
Less than 0.1% by mass D
Industrially, a resist stripper having an allowable resist concentration of about 0.1% by mass or more is practical because no residue is generated during pure water rinsing.
[粘度の評価]
評価対象の試料(レジスト剥離剤)を60℃に加温し、回転式粘度計(CBC社製、商品名:Viscomate Model VM-10A[円柱直径3.5mm])を用いて粘度を測定した。
粘度:
5cP未満 …A
5cP~10cP未満 …B
10cP以上 …C Further, the viscosity of samples (resist stripping agents) 1 to 33 was evaluated as follows.
[Evaluation of viscosity]
A sample to be evaluated (resist stripper) was heated to 60 ° C., and the viscosity was measured using a rotary viscometer (trade name: Viscomate Model VM-10A [cylinder diameter: 3.5 mm] manufactured by CBC).
viscosity:
Less than 5 cP ... A
5 cP to less than 10 cP… B
10cP or more ... C
なお、試料2~29は実施例であり、試料1及び試料30~33は比較例である。 The above results are shown in Table 2 together with the composition of the sample (resist stripper).
EC:PC:GC=65:15:20の混合物100質量部に、表3に示す割合で水を添加した試料(レジスト剥離剤)34~38を調整し、上記したものと同じようにレジスト許容濃度、粘度を評価し、次のように引火性を評価した。
Samples (resist stripping agents) 34 to 38 to which water was added at a ratio shown in Table 3 to 100 parts by mass of a mixture of EC: PC: GC = 65: 15: 20 were prepared, and the resist tolerance was the same as described above. Concentration and viscosity were evaluated, and flammability was evaluated as follows.
評価対象の試料(レジスト剥離剤)について、クリーブランド開放式を採用し、消防法危険物確認試験マニュアルに準拠して引火点の測定及び引火性の評価を行った。
引火性なし …A
引火点100℃以上…B
結果を表3に示す。
なお、試料34~38は実施例である。 [Evaluation of flammability]
For the sample to be evaluated (resist stripper), the Cleveland open type was adopted, and the flash point was measured and the flammability was evaluated in accordance with the Dangerous Goods Confirmation Test Manual.
No flammability ... A
The results are shown in Table 3.
Samples 34 to 38 are examples.
また、実施形態のレジスト剥離剤では、本発明の割合でEC、PC及びGCを含有するため、60℃における粘度も低く作業性に優れることが分かる。 From Tables 2 and 3, it can be seen that the resist stripper of the embodiment has a high resist allowable concentration. Therefore, in the resist stripper of the embodiment, generation of a residue during rinsing with pure water is extremely suppressed. From Table 3, it can be seen that the resist stripper of the embodiment to which water is added has a high flash point, and in particular, Sample 37 and Sample 38 containing water in a predetermined ratio or more have no flammability. Therefore, the resist stripper of the embodiment to which water is added can be made more excellent in safety.
In addition, it can be seen that the resist stripper of the embodiment contains EC, PC, and GC in the ratio of the present invention, and therefore has a low viscosity at 60 ° C. and excellent workability.
模擬実験2(レジスト剥離性能の評価)
[試料の作製]
図3Aは模擬試験2に用いた試料の平面図である。図3Bは同側面図である。
図3Aにおいて、30mm×50mm×0.7mmのガラス基板1(商品名/イーグル2000 (CORNING社製))にノボラック樹脂系ポジ型レジスト(商品名/ZPP-1800-15(日本ゼオン(株)社製))を2μmの膜厚でスリット塗布し、これをプリベーク(110℃で5分)、ポストベーク(130℃で5分)して硬化させた。
次に、このガラス基板1のレジスト塗布部2のほぼ中央に幅 19.0mm、厚さ 0.06mmのポリイミドテープ3(商品名/API-114(チューコーフロー社製))を長さ方向に貼り付けて試料とした。
貼り付けたポリイミドテープ3の幅方向の片側寄りに長さ方向にガラス基板1表面に到達する深さで切り込みを入れて外側部分のテープを除去し、図3A、図3Bに示すように、テープの切断線(符号3と2の境界線)を浸入距離のスタートラインとした。 (Evaluation of resist remover 3)
Simulation experiment 2 (Evaluation of resist stripping performance)
[Preparation of sample]
FIG. 3A is a plan view of a sample used in the
In FIG. 3A, a novolac resin-based positive resist (trade name / ZPP-1800-15 (Nippon Zeon Co., Ltd.) is applied to a glass substrate 1 (trade name / Eagle 2000 (manufactured by CORNING)) of 30 mm × 50 mm × 0.7 mm. Manufactured)) was applied by slitting with a film thickness of 2 μm, and this was prebaked (110 ° C. for 5 minutes) and post-baked (130 ° C. for 5 minutes) to be cured.
Next, a polyimide tape 3 (trade name / API-114 (manufactured by Chuko Flow Co., Ltd.)) having a width of 19.0 mm and a thickness of 0.06 mm is applied to the center of the resist
A tape is cut off at a depth reaching the surface of the
図4Aは浸漬後の評価サンプルの平面図であり、図4Bは同側面図である。
乾燥処理後、図4A、図4Bに示されるような評価サンプルの、ポリイミドテープ3を剥がし、ポリイミドテープの表面を光学顕微鏡で10倍の倍率にて観察し、レジスト剥離剤の侵入距離Sを測定して剥離性能の指標とした。浸入距離Sは、評価サンプル1枚あたり5箇所、計15箇所で測定し、その平均値を浸入距離とした。
実験の結果を表4に示す。
なお、試料39、40は実施例であり、試料41~43は比較例である。 300 mL of the sample was placed in a 1.5 L quartz beaker, and the liquid temperature was maintained at 50 ° C. while stirring at 200 rpm using a hot stirrer. Three evaluation samples were set in a jig made of PFA and immersed in the sample to be evaluated for 1 minute. Next, the evaluation sample after immersion was washed with 18 MΩ · cm of pure water and dried with nitrogen gas.
FIG. 4A is a plan view of the evaluation sample after immersion, and FIG. 4B is a side view thereof.
After the drying treatment, the
The results of the experiment are shown in Table 4.
なお、表4において、試料39は試料34と同じ組成であり、試料2は試料38と同じ組成である。 From Table 4, it can be seen that the samples containing GC (sample 39 and sample 40) have resist stripping performance equivalent to that of EC alone (sample 41) or amine (sample 43).
In Table 4, Sample 39 has the same composition as Sample 34, and
[金属配線に対する腐食性評価]
ガラス基板にCu及びAlをスパッタリングした模擬金属配線試料を60~80℃に加温した評価対象の試料(レジスト剥離剤)200g中に撹拌下で100分間浸漬させた。浸漬後、試料(レジスト剥離剤)中に溶出した金属量をICP-MS(誘導結合プラズマ質量分析装置)で測定し、その結果からCu、Alの1分間あたりのエッチングレートを求めた。
結果を表5に示す。
なお試料44、45は実施例であり、試料46は比較例である。 (Evaluation of resist remover 4)
[Evaluation of corrosiveness to metal wiring]
A simulated metal wiring sample obtained by sputtering Cu and Al on a glass substrate was immersed in 200 g of a sample to be evaluated (resist stripping agent) heated to 60 to 80 ° C. for 100 minutes with stirring. After immersion, the amount of metal eluted in the sample (resist stripper) was measured by ICP-MS (inductively coupled plasma mass spectrometer), and the etching rate per minute of Cu and Al was determined from the result.
The results are shown in Table 5.
Samples 44 and 45 are examples, and sample 46 is a comparative example.
Claims (11)
- (A)炭酸エチレン、炭酸プロピレン、γ-ブチロラクトン及びシクロペンタノンから選ばれる1種以上の50~99質量%と、
(B)炭酸グリセロールの1~50質量%とからなることを特徴とするレジスト剥離剤。 (A) 50 to 99% by mass of one or more selected from ethylene carbonate, propylene carbonate, γ-butyrolactone and cyclopentanone;
(B) A resist remover comprising 1 to 50% by mass of glycerol carbonate. - 前記(A)が炭酸エチレン及び炭酸プロピレンから選ばれる1種以上であることを特徴とする請求項1記載のレジスト剥離剤。 The resist remover according to claim 1, wherein (A) is at least one selected from ethylene carbonate and propylene carbonate.
- (A)炭酸エチレンの20~80質量%と、炭酸プロピレンの5~30質量%と、 (B)炭酸グリセロールの5~50質量%とからなることを特徴とする請求項1記載のレジスト剥離剤。 2. The resist stripper according to claim 1, comprising (A) 20 to 80% by mass of ethylene carbonate, 5 to 30% by mass of propylene carbonate, and (B) 5 to 50% by mass of glycerol carbonate. .
- (A)炭酸エチレンの55~75質量%と、炭酸プロピレンの5~25質量%と、 (B)炭酸グリセロールの10~30質量%とからなることを特徴とする請求項1記載のレジスト剥離剤。 2. The resist remover according to claim 1, comprising (A) 55 to 75% by mass of ethylene carbonate, 5 to 25% by mass of propylene carbonate, and (B) 10 to 30% by mass of glycerol carbonate. .
- 請求項1記載のレジスト剥離剤全体の100質量部に対し、水を30質量部以下含むことを特徴とするレジスト剥離剤。 A resist remover comprising 30 parts by mass or less of water with respect to 100 parts by mass of the entire resist remover according to claim 1.
- 請求項2記載のレジスト剥離剤全体の100質量部に対し、水を30質量部以下含むことを特徴とするレジスト剥離剤。 A resist remover comprising 30 parts by mass or less of water with respect to 100 parts by mass of the entire resist remover according to claim 2.
- 請求項3記載のレジスト剥離剤全体の100質量部に対し、水を30質量部以下含むことを特徴とするレジスト剥離剤。 A resist remover comprising 30 parts by mass or less of water with respect to 100 parts by mass of the entire resist remover according to claim 3.
- 請求項4記載のレジスト剥離剤全体の100質量部に対し、水を30質量部以下含むことを特徴とするレジスト剥離剤。 A resist remover comprising 30 parts by mass or less of water with respect to 100 parts by mass of the entire resist remover according to claim 4.
- 60℃における粘度が10cP以下であることを特徴とする請求項1乃至8のいずれか1項記載のレジスト剥離剤。 The resist remover according to any one of claims 1 to 8, wherein the viscosity at 60 ° C is 10 cP or less.
- 引火点が100℃以上であることを特徴とする請求項1乃至8のいずれか1項記載のレジスト剥離剤。 The resist stripper according to any one of claims 1 to 8, wherein the flash point is 100 ° C or higher.
- 引火点が100℃以上であることを特徴とする請求項9記載のレジスト剥離剤。 The resist stripping agent according to claim 9, having a flash point of 100 ° C. or higher.
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- 2012-10-02 KR KR1020147000973A patent/KR102021158B1/en active IP Right Grant
- 2012-10-02 WO PCT/JP2012/006286 patent/WO2014002151A1/en active Application Filing
- 2012-10-02 JP JP2013546474A patent/JP5437541B1/en active Active
- 2012-10-02 CN CN201280038198.1A patent/CN103733137B/en active Active
- 2012-10-16 TW TW101138083A patent/TWI572999B/en not_active IP Right Cessation
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WO2018020837A1 (en) * | 2016-07-28 | 2018-02-01 | 野村マイクロ・サイエンス株式会社 | Resist stripper composition |
Also Published As
Publication number | Publication date |
---|---|
JPWO2014002151A1 (en) | 2016-05-26 |
JP5437541B1 (en) | 2014-03-12 |
TW201400996A (en) | 2014-01-01 |
CN103733137A (en) | 2014-04-16 |
KR102021158B1 (en) | 2019-09-11 |
CN103733137B (en) | 2019-06-25 |
KR20150037719A (en) | 2015-04-08 |
TWI572999B (en) | 2017-03-01 |
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