WO2018061064A1 - Liquide d'élimination des réserves - Google Patents

Liquide d'élimination des réserves Download PDF

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Publication number
WO2018061064A1
WO2018061064A1 PCT/JP2016/004436 JP2016004436W WO2018061064A1 WO 2018061064 A1 WO2018061064 A1 WO 2018061064A1 JP 2016004436 W JP2016004436 W JP 2016004436W WO 2018061064 A1 WO2018061064 A1 WO 2018061064A1
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Prior art keywords
mass
water
hydrazine
resist
hydrazine monohydrate
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PCT/JP2016/004436
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English (en)
Japanese (ja)
Inventor
真一郎 淵上
佑典 鬼頭
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パナソニックＩｐマネジメント株式会社
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Priority to JP2017523005A priority Critical patent/JP6160893B1/ja
Priority to CN201680034620.4A priority patent/CN107995960B/zh
Priority to PCT/JP2016/004436 priority patent/WO2018061064A1/fr
Priority to TW106133105A priority patent/TWI629353B/zh
Publication of WO2018061064A1 publication Critical patent/WO2018061064A1/fr

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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

Definitions

  • the present invention is a stripping solution for stripping a resist used in the manufacture of display devices such as liquid crystal and organic EL and semiconductors. More specifically, even a hard-baked resist film can remove a resist, and further, aluminum
  • the present invention also relates to a resist stripper that can be said to be substantially free from corrosion even with respect to a film and a copper film.
  • a flat panel display such as a liquid crystal or an organic EL (Electro-Luminescence) is required to have a large screen.
  • FPD flat panel display
  • small high-definition screens are required for notebook PCs, tablet PCs, and smartphones.
  • a TFT Thin Film Transistor
  • Cu wiring Cu / Mo laminated wiring
  • TFTs using Al wiring are used for small high-definition screens.
  • Cu is also called copper
  • Mo is called molybdenum
  • Al is also called aluminum.
  • Some panel manufacturers may produce TFTs using Cu wiring and TFTs mixed with Cu wiring and Al wiring in one factory.
  • TFTs in which Cu wiring and Al wiring are mixed if the resist stripping process can be shared between the use of Al wiring and the use of Cu wiring in the resist film peeling process, the production cost and equipment can be reduced. Can be reduced.
  • a water-based positive photoresist stripping solution generally has a composition comprising alkanolamine, a polar solvent, and water, and is used after being heated to about 40 to 50 ° C. in a resist stripping apparatus.
  • Alkanolamine is an essential component for solubilizing the carbonyl group of a DNQ (diazonaphthoquinone) compound, which is an alkali insolubilizing agent, in a positive photoresist stripping solution in a polar solvent and water by nucleophilic action.
  • Alkanolamines are classified as primary, secondary, and tertiary depending on the number of substituents other than hydrogen bonded to the nitrogen element. Among these, it is known that the smaller the series, the stronger the basicity and the stronger the nucleophilicity.
  • the smaller the series the stronger the power to solubilize the DNQ compound, which is an alkali insolubilizing agent, in a polar solvent or water, and a stronger resist stripping performance.
  • alkanolamine is known to have a chelating action on Cu.
  • the chelating action for Cu solubilizes Cu and thus corrodes the Cu film.
  • the chelating action for Cu is stronger as the alkanolamine series is smaller as is the case with basicity and nucleophilicity. Therefore, the alkanolamine with a smaller series corrodes the Cu film more strongly.
  • a-Si amorphous silicon
  • LTPS low-temperature polysilicon
  • IGZO oxide semiconductor
  • ⁇ Al wiring is not corrosive (chelating) by alkanolamine. Therefore, in order to remove the modified resist, it is common to use a primary alkanolamine having strong release performance.
  • Patent Document 1 discloses a resist stripping solution containing a compound represented by the formula (1) and a solvent. It is said that this resist stripper can also be used in the resist stripping process for Cu wiring and Al wiring.
  • Patent Document 2 discloses a resist stripping solution having a stripping force equivalent to that of an Al wiring resist stripping solution using a primary alkanolamine in spite of the use of a tertiary alkanolamine.
  • the stripping solution contains a tertiary amine, a polar solvent, water, a cyclic amine, a sugar alcohol, and a reducing agent, and the five-membered cyclic amine has a composition having pyrrolidine or pyrrolidine having a substituent at the 3-position. is there.
  • JP 2012-514765 A Patent No. 5279921
  • JP 2016-085378 A Patent No. 5885041
  • Patent Document 2 The stripping solution of Patent Document 2 can be shared in the resist stripping process for Cu wiring (including Cu / Mo laminated wiring) and Al wiring. Further, even if hard baking is applied to the resist film, the resist film can be peeled off.
  • the present invention has been conceived in view of the above problems, and provides a resist stripping solution that can strip even a resist baked at a higher temperature than in the past.
  • a resist stripping solution that can strip even a resist baked at a higher temperature than in the past.
  • the resist stripper according to the present invention is: Secondary amines, As a polar solvent, 1,3-dimethyl-2-imidazolidinone (DMI), Including water, Containing hydrazine as an additive,
  • DMI 1,3-dimethyl-2-imidazolidinone
  • the water content is 10.0% by mass or more and less than 31.0% by mass.
  • the resist stripping solution according to the present invention uses a secondary amine, even a resist baked at a higher temperature than before can be surely stripped. Furthermore, since the resist stripping solution according to the present invention contains 1,3-dimethyl-2-imidazolidinone (DMI) as a polar solvent, it does not contain Cu, Mo, Al, etc. even though it contains secondary amines. Corrosion to metal is suppressed.
  • DMI 1,3-dimethyl-2-imidazolidinone
  • the resist stripping solution according to the present invention uses a secondary amine having a high boiling point, it can be recycled after use.
  • the resist stripping solution according to the present invention is excellent in bath life, and the resist stripping ability does not change even if it is left for 12 hours or more in an open air state or stored in a sealed state for 4 days.
  • the resist film from which the resist stripper according to the present invention is peeled is assumed to be a positive resist.
  • the positive resist includes a novolac resin as a resin, and a diazonaphthoquinone (DNQ) compound is used as a photosensitive agent.
  • DNQ diazonaphthoquinone
  • This exposure turns the DNQ compound into indenketene.
  • indenketene associates with water, it turns into indenecarboxylic acid and dissolves in water.
  • the novolac resin originally has a property of being dissolved in an alkaline solution, but the melting point is protected by a DNQ compound.
  • the DNQ compound is altered by exposure and is dissolved in a developer containing water, so that the novolak resin is also dissolved. In this way, patterning of the resist film is completed.
  • the substrate on which the patterning is completed with the resist film is subjected to wet etching or dry etching processing after post-baking.
  • Post bake is performed in order to advance polymerization of the novolak resin and the DNQ compound in the resist film to some extent.
  • the heat treatment is performed at 140 ° C. for about 5 minutes.
  • hard baking means heating conditions at 170 ° C. for 30 minutes or more. When the baking temperature rises, the novolak resin and the DNQ compound rapidly polymerize and firmly adhere to the underlying metal film, making it difficult to dissolve.
  • the resist stripping solution according to the present invention is also intended for a resist film that has undergone such hard baking.
  • the resist stripping solution according to the present invention contains a secondary amine, a polar solvent, and a reducing agent.
  • a secondary amine one having a boiling point higher than that of water and not azeotropic with water is desirable. This is because when the stripping solution is recycled, it is separated from water.
  • N-methylethanolamine hereinafter also referred to as “MMA”, boiling point 155 ° C., CAS No. 109-83-1
  • N-ethylethanolamine hereinafter also referred to as “EEA”, boiling point 170 ° C.
  • CAS number 110-73-6 can be preferably used. These may be mixed.
  • these may be 0.5% by mass or more and 9.0% by mass or less, preferably 1.0% by mass or more and 8.0% by mass or less, most preferably 2.0% by mass with respect to the total amount of the stripping solution.
  • 7.0 mass% or less is good. When there are few secondary amines, the hard-baked resist cannot be peeled off. On the other hand, when too much, metal damage will become large.
  • performance even if it contains 9.0 mass%, it has confirmed that a problem does not generate
  • the polar solvent may be an organic solvent having an affinity for water (referred to as a water-soluble organic solvent). Moreover, it is more suitable if the mixing property with said secondary amine is favorable.
  • 1,3-dimethyl-2-imidazolidinone (hereinafter also referred to as “DMI”, CAS No. 80-73-9) can be suitably used.
  • the polar solvent is composed of a water-soluble organic solvent and water.
  • the polar solvent is an amount obtained by removing the secondary amine and the reducing agent described later with respect to the total amount of the stripping solution. Specifically, it is 90.60 mass% or more and 99.47 mass% or less.
  • the amount of water is preferably 10.0% by mass or more and less than 31.0% by mass with respect to the total amount of the resist stripping solution. This is because when the amount of water is too much, there arises a problem that Al is corroded when the metal film is Al.
  • 1,3-Dimethyl-2-imidazolidinone (DMI) may be the remainder of the polar solvent. By itself, 1,3-dimethyl-2-imidazolidinone (DMI) stabilizes hydrazine and mitigates damage to the surface and cross-section of secondary amine and hydrazine metal films.
  • the reducing agent hydrazine (hereinafter also referred to as “HN”, CAS No. 302-01-2) can be suitably used. Addition of a reducing agent suppresses Mo undercut by secondary amine.
  • the reducing agent is desirably in the range of 0.03% by mass to 0.4% by mass with respect to the total amount of the resist stripping solution. More preferably, it is the range of 0.06 mass% or more and 0.2 mass% or less.
  • Hydrazine may be hydrated (hydrazine monohydrate: described as “HN ⁇ H 2 O”) from the viewpoint of safe handling.
  • resist stripping solution examples and comparative examples of resist stripping solutions according to the present invention are shown below.
  • the resist stripping solution was evaluated for three points: “resist stripping property”, “corrosiveness of metal film”, and “bus life”.
  • a silicon thermal oxide film having a thickness of 100 nm was formed on a silicon substrate, and a copper film having a thickness of 300 nm was formed on the silicon thermal oxide film by sputtering.
  • a positive resist solution was applied onto the copper film by spin coating to prepare a resist film. After the resist film was dried, it was exposed using a wiring pattern mask. Then, the resist in the exposed portion was removed with a developer. That is, there is a state where there is a portion where the resist film of the wiring pattern remains on the copper film and a portion where the copper film is exposed. Thereafter, the entire silicon substrate was post-baked at 170 ° C. for 30 minutes.
  • the exposed copper film was removed by etching using an overwater copper etchant. After the etching of the copper film was completed, the remaining resist film on the copper pattern was stripped using a sample resist stripping solution. The treatment time for peeling was 15 minutes, and the time until peeling was measured. Judgment was made by observing with an optical microscope as to whether or not peeling was possible.
  • ⁇ Corrosiveness of metal film> The corrosivity of the metal film was evaluated as follows. First, a silicon thermal oxide film having a thickness of 100 nm was formed on a silicon substrate. Next, a molybdenum film is formed to a thickness of 20 nm on the silicon thermal oxide film on the silicon substrate, and a copper film is subsequently formed to a thickness of 300 nm to produce a Cu / Mo laminated film sample. did. This is referred to as “Cu / Mo”. In addition, an aluminum film was formed to a thickness of 300 nm on the silicon thermal oxide film on the silicon substrate to produce an Al film sample. This is referred to as “Al”.
  • the base material for corrosivity evaluation is composed of either a Cu / Mo film or an Al film formed on a silicon thermal oxide film on a silicon substrate, and a resist layer formed in a wiring shape thereon.
  • Etching was performed by immersing these corrosive evaluation base materials in an etchant for copper film or aluminum film for the time of just etching. Thereafter, the corrosive evaluation base material after etching was immersed in a sample resist stripper for 4 minutes to strip the resist film. After the corrosive evaluation base material immersed in the sample resist stripper for 4 minutes was washed and dried, the film surface was observed. Moreover, the wiring part was cut
  • the film surface and the cut surface were observed using SEM (Scanning Electron Microscope) (Hitachi: SU8020 type) under the conditions of an acceleration voltage of 1 kV and 30,000 to 50,000 times.
  • SEM Sccanning Electron Microscope
  • FIG. 1A shows a cut surface shape in the case of “Al”.
  • the cut surface shape of the just-etched portion has a taper angle 5 of approximately 30 ° to 60 ° with respect to the substrate 1.
  • the film part 2 is an Al film.
  • FIG. 1B shows the case of “Cu / Mo”.
  • the upper film portion 2 (Cu) has a taper angle 5.
  • the underlayer 3 (Mo) is preferably etched along the tapered surface 6 of the film part 2. However, as shown in FIG. 1B, there may be etching residue from the film portion 2.
  • Corrosion is evaluated by observing this cross-sectional shape, and if corrosion is confirmed on either the film part 2 or the surface 4 of the film part 2 or the underlying layer 3, it is judged as a cross ( ⁇ ) and the corrosion is observed. If it was not done, it was judged as a circle.
  • the resist stripping solution is a mixed composition of materials such as an amine, an organic solvent, and a reducing agent. Carbon dioxide in the air dissolves in the stripping solution and becomes carbonic acid / bicarbonate ions, or reacts with amines to generate carbamate ions. As a result, the stripping force decreases and metal damage increases.
  • the resist stripping property test was performed by leaving the resist stripping solution at room temperature in the atmosphere for 0 hours, 6 hours, and 12 hours, and "Cu / Mo", "Al The surface and the cross-sectional state of "were observed with SEM.
  • the evaluation method is the same as in the case of ⁇ resist peelability> and ⁇ metal corrosivity>.
  • the resist stripping solution is carried in a container.
  • the container cannot be stored at room temperature, the usability in the factory will be extremely poor. Therefore, the change of components was also examined by storage at room temperature.
  • Evaluation method was put in a sealed container and left at room temperature for 4 days to measure the stability of hydrazine.
  • hydrazine was reduced by 1% or more compared to immediately after preparation, it was “X”, and when it was less than 1%, it was “ ⁇ ”.
  • sample resist stripping solution was prepared as follows.
  • Example 1 N-methylethanolamine was used as the secondary amine. N-methylethanolamine (MMA) 5.0% by mass As a polar solvent, water and 1,3-dimethyl-2-imidazolidinone were mixed. 1,3-Dimethyl-2-imidazolidinone (DMI) 74.9% by mass Water 20.0% by mass Hydrazine was used as a reducing agent. Hydrazine monohydrate (HN ⁇ H 2 O) 0.1% by mass The above was mixed and stirred to obtain the sample resist stripping solution of Example 1.
  • hydrazine monohydrate corresponds to 0.064% by mass of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 20.036% by mass including the amount of hydrazine monohydrate added.
  • hydrazine monohydrate when used, it has the same meaning.
  • Example 2 N-ethylethanolamine was used as the secondary amine.
  • N-ethylethanolamine (EEA) 5.0% by mass
  • water and 1,3-dimethyl-2-imidazolidinone were mixed.
  • 1,3-Dimethyl-2-imidazolidinone (DMI) 74.9% by mass
  • Water 20.0% by mass Hydrazine was used as a reducing agent.
  • Example 2 has a composition obtained by replacing N-methylethanolamine (MMA)) as the secondary amine of Example 1 with N-ethylethanolamine (EEA).
  • MMA N-methylethanolamine
  • EOA N-ethylethanolamine
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 20.036% by mass including the amount of hydrazine monohydrate added.
  • Example 3 N-methylethanolamine was used as the secondary amine. N-methylethanolamine (MMA) 5.0% by mass As a polar solvent, water and 1,3-dimethyl-2-imidazolidinone were mixed. 1,3-dimethyl-2-imidazolidinone (DMI) 70.9% by mass 24.0% by mass of water Hydrazine was used as a reducing agent. Hydrazine monohydrate (HN ⁇ H 2 O) 0.1% by mass The above was mixed and stirred to obtain the sample resist stripping solution of Example 3.
  • Example 3 is a composition in which the ratio of DMI and water in the polar solvent of Example 1 is changed.
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 24.036% by mass including the amount of hydrazine monohydrate added.
  • Example 4 N-methylethanolamine was used as the secondary amine. N-methylethanolamine (MMA) 5.0% by mass As a polar solvent, water and 1,3-dimethyl-2-imidazolidinone were mixed. 1,3-Dimethyl-2-imidazolidinone (DMI) 68.9% by mass 26.0% by weight of water Hydrazine was used as a reducing agent. Hydrazine monohydrate (HN ⁇ H 2 O) 0.1% by mass The above was mixed and stirred to obtain a sample resist stripping solution of Example 4.
  • Example 4 is a composition in which the ratio of the DMI of the polar solvent and the water in Example 1 was changed.
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of water is 26.036% by mass including the amount of hydrazine monohydrate added.
  • Example 5 N-methylethanolamine was used as the secondary amine. N-methylethanolamine (MMA) 5.0% by mass As a polar solvent, water and 1,3-dimethyl-2-imidazolidinone were mixed. 1,3-dimethyl-2-imidazolidinone (DMI) 66.9% by mass 28.0% by weight of water Hydrazine was used as a reducing agent. Hydrazine monohydrate (HN ⁇ H 2 O) 0.1% by mass The above was mixed and stirred to obtain a sample resist stripping solution of Example 5.
  • Example 5 is a composition in which the ratio of DMI of the polar solvent of Example 1 to water was changed.
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 28.036% by mass including the amount of hydrazine monohydrate added.
  • Example 6 N-methylethanolamine was used as the secondary amine.
  • N-methylethanolamine (MMA) 2.0% by mass
  • water and 1,3-dimethyl-2-imidazolidinone were mixed.
  • 1,3-Dimethyl-2-imidazolidinone (DMI) 73.9% by mass 24.0% by mass of water
  • Hydrazine was used as a reducing agent.
  • Example 6 is a composition in which the amount of secondary amine of Example 1 is reduced.
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 24.036% by mass including the amount of hydrazine monohydrate added.
  • Example 7 N-methylethanolamine was used as the secondary amine. N-methylethanolamine (MMA) 3.0% by mass As a polar solvent, water and 1,3-dimethyl-2-imidazolidinone were mixed. 1,3-Dimethyl-2-imidazolidinone (DMI) 72.9% by mass 24.0% by mass of water Hydrazine was used as a reducing agent. Hydrazine monohydrate (HN ⁇ H 2 O) 0.1% by mass The above was mixed and stirred to obtain a sample resist stripping solution of Example 7.
  • Example 7 is a composition in which the amount of secondary amine of Example 1 is reduced.
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 24.036% by mass including the amount of hydrazine monohydrate added.
  • Example 8 N-methylethanolamine was used as the secondary amine.
  • N-methylethanolamine (MMA) 4.0% by mass
  • water and 1,3-dimethyl-2-imidazolidinone were mixed.
  • 1,3-Dimethyl-2-imidazolidinone (DMI) 71.9% by mass 24.0% by mass of water
  • Hydrazine was used as a reducing agent.
  • Example 8 is a composition in which the amount of secondary amine of Example 1 is reduced.
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 24.036% by mass including the amount of hydrazine monohydrate added.
  • Example 9 N-methylethanolamine was used as the secondary amine.
  • N-methylethanolamine (MMA) 5.0% by mass
  • water and 1,3-dimethyl-2-imidazolidinone were mixed.
  • 1,3-dimethyl-2-imidazolidinone (DMI) 70.9% by mass 24.0% by mass of water
  • Hydrazine was used as a reducing agent.
  • Example 9 is a composition having the same amount as the secondary amine of Example 1. However, the amount of water is different from Example 1. In addition, 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine. The remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 24.036% by mass including the amount of hydrazine monohydrate added.
  • Example 10 N-methylethanolamine was used as the secondary amine.
  • N-methylethanolamine (MMA) 6.0% by mass
  • water and 1,3-dimethyl-2-imidazolidinone were mixed.
  • 1,3-dimethyl-2-imidazolidinone (DMI) 69.9% by mass 24.0% by mass of water
  • Hydrazine was used as a reducing agent.
  • Example 10 is a composition in which the amount of secondary amine of Example 1 is increased.
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 24.036% by mass including the amount of hydrazine monohydrate added.
  • N-methylethanolamine was used as the secondary amine.
  • N-methylethanolamine (MMA) 7.0% by mass
  • water and 1,3-dimethyl-2-imidazolidinone were mixed.
  • 1,3-Dimethyl-2-imidazolidinone (DMI) 68.9% by mass 24.0% by mass of water
  • Hydrazine was used as a reducing agent.
  • Example 11 is a composition in which the amount of secondary amine of Example 1 is increased.
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 24.036% by mass including the amount of hydrazine monohydrate added.
  • Comparative Example 1 is a composition obtained by replacing the polar solvent 1,3-dimethyl-2-imidazolidinone (DMI) of Example 1 with N-methylformamide (NMF).
  • DMI 1,3-dimethyl-2-imidazolidinone
  • NMF N-methylformamide
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 20.036% by mass including the amount of hydrazine monohydrate added.
  • N-methylethanolamine was used as the secondary amine.
  • N-methylethanolamine (MMA) 5.0% by mass
  • water and N, N-dimethylformamide were mixed.
  • N, N-dimethylformamide (DMF: CAS No. 68-12-2) 74.9% by mass
  • Water 20.0% by mass Hydrazine was used as a reducing agent.
  • Hydrazine monohydrate (HN ⁇ H 2 O) 0.1% by mass The above was mixed and stirred to obtain a sample resist stripping solution of Comparative Example 2.
  • Comparative Example 2 is a composition obtained by replacing the polar solvent 1,3-dimethyl-2-imidazolidinone (DMI) of Example 1 with N, N-dimethylformamide (DMF).
  • DMI 1,3-dimethyl-2-imidazolidinone
  • DMF N, N-dimethylformamide
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 20.036% by mass including the amount of hydrazine monohydrate added.
  • Comparative Example 3 has a composition obtained by replacing the polar solvent 1,3-dimethyl-2-imidazolidinone (DMI) of Example 1 with 2-pyrrolidone (2P).
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 20.036% by mass including the amount of hydrazine monohydrate added.
  • Comparative Example 4 is a composition obtained by replacing the polar solvent 1,3-dimethyl-2-imidazolidinone (DMI) of Example 1 with 1-methyl-2-pyrrolidone (NMP).
  • DMI 1,3-dimethyl-2-imidazolidinone
  • NMP 1-methyl-2-pyrrolidone
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 20.036% by mass including the amount of hydrazine monohydrate added.
  • Comparative Example 5 is a composition obtained by replacing the polar solvent 1,3-dimethyl-2-imidazolidinone (DMI) of Example 1 with 1-ethyl-2-pyrrolidone (NEP).
  • DMI 1,3-dimethyl-2-imidazolidinone
  • NEP 1-ethyl-2-pyrrolidone
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 20.036% by mass including the amount of hydrazine monohydrate added.
  • Comparative Example 6 is a composition obtained by replacing the polar solvent 1,3-dimethyl-2-imidazolidinone (DMI) of Example 1 with ⁇ -butyrolactone (GBL).
  • DMI 1,3-dimethyl-2-imidazolidinone
  • GBL ⁇ -butyrolactone
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 20.036% by mass including the amount of hydrazine monohydrate added.
  • Comparative Example 7 is a composition obtained by replacing the polar solvent 1,3-dimethyl-2-imidazolidinone (DMI) of Example 1 with ethylene carbonate (EC).
  • EC ethylene carbonate
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 20.036% by mass including the amount of hydrazine monohydrate added.
  • Comparative Example 8 is a composition obtained by replacing the secondary amine N-methylethanolamine (MMA) of Example 1 with a tertiary amine N-methyldiethanolamine (MDEA).
  • MMA secondary amine N-methylethanolamine
  • MDEA tertiary amine N-methyldiethanolamine
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 20.036% by mass including the amount of hydrazine monohydrate added.
  • Comparative Example 9 is a composition obtained by replacing the secondary amine N-methylethanolamine (MMA) of Example 1 with the cyclic amine pyrrolidine (PRL).
  • MMA secondary amine N-methylethanolamine
  • PRL cyclic amine pyrrolidine
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 20.036% by mass including the amount of hydrazine monohydrate added.
  • Comparative Example 10 has a composition obtained by replacing the secondary amine N-methylethanolamine (MMA) of Example 1 with the cyclic amine hydroxyethylpiperazine (OH-PIZ).
  • MMA secondary amine N-methylethanolamine
  • OH-PIZ cyclic amine hydroxyethylpiperazine
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 20.036% by mass including the amount of hydrazine monohydrate added.
  • Comparative Example 11 is a composition obtained by replacing the secondary amine N-methylethanolamine (MMA) of Example 1 with a primary amine monoethanolamine (MEA).
  • MMA secondary amine N-methylethanolamine
  • MEA primary amine monoethanolamine
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of the water is 20.036% by mass including the amount of hydrazine monohydrate added.
  • Comparative Example 12 N-methylethanolamine was used as the secondary amine. N-methylethanolamine (MMA) 5.0% by mass As a polar solvent, water and 1,3-dimethyl-2-imidazolidinone were mixed. 1,3-Dimethyl-2-imidazolidinone (DMI) 75.0% by mass Water 20.0% by mass No reducing agent was added. The above was mixed and stirred to obtain a sample resist stripping solution of Comparative Example 12. Comparative Example 12 is a composition in which the reducing agent hydrazine (HN) of Example 1 was omitted.
  • HN reducing agent hydrazine
  • Comparative Example 13 N-methylethanolamine was used as the secondary amine. N-methylethanolamine (MMA) 5.0% by mass As a polar solvent, water and 1,3-dimethyl-2-imidazolidinone were mixed. 1,3-dimethyl-2-imidazolidinone (DMI) 74.5% by mass Water 20.0% by mass Sorbitol was used as an additive. Sorbitol (Stol: CAS No. 50-70-4) 0.5% by mass The above was mixed and stirred to obtain a sample resist stripping solution of Comparative Example 13. Comparative Example 13 is a composition obtained by replacing the additive (reducing agent: hydrazine (HN)) of Example 1 with sorbitol.
  • HN hydrazine
  • Comparative Example 14 N-methylethanolamine was used as the secondary amine. N-methylethanolamine (MMA) 5.0% by mass As a polar solvent, water and 1,3-dimethyl-2-imidazolidinone were mixed. 1,3-dimethyl-2-imidazolidinone (DMI) 74.5% by mass Water 20.0% by mass Diglycerin was used as an additive. Diglycerin (CAS No. 627-82-7) 0.5% by mass The above was mixed and stirred to obtain a sample resist stripping solution of Comparative Example 14. Comparative Example 14 is a composition obtained by replacing the additive (reducing agent: hydrazine (HN)) of Example 1 with diglycerin.
  • HN hydrazine
  • Comparative Example 15 N-methylethanolamine was used as the secondary amine. N-methylethanolamine (MMA) 5.0% by mass As a polar solvent, water and 1,3-dimethyl-2-imidazolidinone were mixed. 1,3-dimethyl-2-imidazolidinone (DMI) 74.5% by mass Water 20.0% by mass Saccharin was used as an additive. Saccharin (CAS No. 81-07-2) 0.5% by mass The above was mixed and stirred to obtain a sample resist stripping solution of Comparative Example 15. Comparative Example 15 is a composition obtained by replacing the additive of Example 1 (reducing agent: hydrazine (HN)) with saccharin.
  • reducing agent hydrazine (HN)
  • Comparative Example 16 N-methylethanolamine was used as the secondary amine. N-methylethanolamine (MMA) 5.0% by mass As a polar solvent, water and 1,3-dimethyl-2-imidazolidinone were mixed. 1,3-dimethyl-2-imidazolidinone (DMI) 74.5% by mass Water 20.0% by mass Polyethylene glycol 400 (PEG400) was used as an additive. Polyethylene glycol 400 (PEG400: CAS number 25322-68-3) 0.5% by mass The above was mixed and stirred to obtain a sample resist stripping solution of Comparative Example 16. Comparative Example 16 is a composition obtained by replacing the additive (reducing agent: hydrazine (HN)) of Example 1 with polyethylene glycol 400.
  • reducing agent hydrazine (HN)
  • N-methylethanolamine was used as the secondary amine.
  • N-methylethanolamine (MMA) 5.0% by mass
  • water and 1,3-dimethyl-2-imidazolidinone were mixed.
  • 1,3-dimethyl-2-imidazolidinone (DMI) 63.9% by mass 31.0% by weight of water
  • Hydrazine was used as a reducing agent.
  • Comparative Example 17 is a composition in which the amount of water in Example 1 was increased from 20.0% by mass to 31.0% by mass.
  • 0.1 mass% of hydrazine monohydrate corresponds to 0.064 mass% of hydrazine.
  • the remaining 0.036% by mass of hydrazine monohydrate is water. Therefore, it can be said that the composition ratio of water is 31.036% by mass including the amount of hydrazine monohydrate added.
  • Table 1 shows the compositions and evaluation results of Example 1 and Comparative Examples 1 to 7.
  • Table 2 shows the compositions and evaluation results of Examples 1 and 2 and Comparative Examples 8 to 11.
  • Table 3 shows the compositions and evaluation results of Example 1 and Comparative Examples 12 to 16.
  • Table 4 shows the compositions and evaluation results of Examples 1, 3 to 5 and Comparative Example 17.
  • Table 5 shows the compositions and evaluation results of Examples 6 to 11.
  • Table 1 shows the compositions and evaluation results of Example 1 and Comparative Examples 1 to 7. See Example 1.
  • MMA secondary amine N-methylethanolamine
  • DMI 1,3-dimethyl-2-imidazolidinone
  • Table 1 shows the compositions and evaluation results of Example 1 and Comparative Examples 1 to 7. See Example 1.
  • MMA secondary amine N-methylethanolamine
  • DMI 1,3-dimethyl-2-imidazolidinone
  • the peeling force did not change even after 12 hours had elapsed in the bath life when the peeling solution was left open to the atmosphere. Furthermore, no decrease in hydrazine was observed even after 4 days of sealed storage.
  • N-methylformamide NMF was used in place of the polar solvent 1,3-dimethyl-2-imidazolidinone (DMI) of Example 1.
  • DMI 1,3-dimethyl-2-imidazolidinone
  • Comparative Example 2 N, N-dimethylformamide (DMF) was used instead of DMI.
  • Comparative Example 3 uses 2-pyrrolidone (2P) instead of DMI.
  • 1-methyl-2-pyrrolidone (NMP) was used instead of DMI.
  • 1-ethyl-2-pyrrolidone NEP was used instead of DMI.
  • ⁇ -butyrolactone GBL was used instead of DMI.
  • Comparative Example 7 uses ethylene carbonate (EC) instead of DMI.
  • Comparative Example 1 was peeled well with respect to peelability immediately after preparation. However, when left in the air, damage occurred on the cross section and surface of “Cu / Mo”. In addition, a decrease in hydrazine was observed when left in a sealed state for 4 days.
  • Comparative Example 2 was also peeled well for peelability immediately after preparation. However, when left in the atmosphere, damage occurred on the cross section and surface of “Cu / Mo” after 12 hours. In addition, a decrease in hydrazine was observed when left in a sealed state for 4 days.
  • Comparative Example 4 there was no problem with the peelability immediately after preparation and the damage to the metal film after standing in the atmosphere for 12 hours. However, a decrease in hydrazine was observed after standing for 4 days.
  • Comparative Example 5 there was no problem with the peelability immediately after preparation and the damage to the metal film after being left in the atmosphere for 12 hours. However, a decrease in hydrazine was observed after standing for 4 days.
  • Comparative Example 6 was peeled well with respect to peelability immediately after preparation. However, damage occurred on the cross section and surface of “Cu / Mo”. Therefore, no test was conducted for bus life.
  • the secondary amine N-methylethanolamine (MMA) of Example 1 was used, and a mixture of only 1,3-dimethyl-2-imidazolidinone (DMI) and water was used as the polar solvent, and hydrazine was used.
  • Example 2 shows the compositions and evaluation results of Examples 1 and 2 and Comparative Examples 8 to 11. Since Example 1 is shown again, it is shown in parentheses. In Example 2, N-ethylethanolamine (EEA) was used instead of N-methylethanolamine (MMA) as the secondary amine. In Example 2, the peel strength, the damage to the metal and the bath life were as good as in Example 1.
  • EOA N-ethylethanolamine
  • MMA N-methylethanolamine
  • Comparative Examples 8 to 11 are cases where the amine was changed.
  • the tertiary amine N-methyldiethanolamine (MDEA) was used as the amine.
  • Comparative Example 9 is a case where pyrrolidine (PRL) of a cyclic amine is used
  • Comparative Example 10 is a case where hydroxyethyl piperazine (OH-PIZ) of a cyclic amine is used.
  • Comparative Example 11 is an example using monoethanolamine (MEA) as a primary amine.
  • Comparative Examples 8, 9, and 10 could not remove the hard-baked resist. Therefore, no test was conducted for bus life. Moreover, the primary amine monoethanolamine (MEA) was able to remove the hard-baked resist immediately after preparation, but damaged the surface and cross section of “Cu / Mo”. Therefore, the test for the bath life was not performed for Comparative Example 11 as well.
  • MEA primary amine monoethanolamine
  • Comparative Example 12 is a composition that does not contain hydrazine (hydrazine monohydrate (HN ⁇ H 2 O)). In Comparative Example 12, the hard-baked resist could be removed immediately after preparation. However, film damage of “Cu / Mo” occurred.
  • Comparative Example 13 contains sorbitol (Stol) as an additive.
  • Styrol sorbitol
  • diglycerin is added as an additive.
  • the hard-baked resist was not able to be peeled off immediately after preparation.
  • Comparative Example 15 contains saccharin as an additive.
  • PEG 400 polyethylene glycol 400
  • Comparative Examples 15 and 16 the hard-baked resist could be peeled off immediately after preparation. However, in both comparative examples, damage was caused on the cross section of “Cu / Mo”.
  • hydrazine hydrazine monohydrate (HN ⁇ H 2 O)
  • HN ⁇ H 2 O hydrazine monohydrate
  • Table 4 shows the compositions and evaluation results of Examples 1, 3 to 5 and Comparative Example 17. Since Example 1 is shown again, it is shown in parentheses. Table 4 is a study on the amount of water. Example 3 has a moisture content of 24.0% by mass, Example 4 has a moisture content of 26.0% by mass, and Example 5 has a moisture content of 28.0% by mass. Is. On the other hand, Comparative Example 17 increases the water content to 31.0% by mass.
  • Table 5 shows the compositions and evaluation results of Examples 6 to 11.
  • Examples 6 to 11 examine the amount of amine. The amount of water is all adjusted to 24.0% by mass. The table was arranged from the one with the smallest amount of amine to the one with the larger amount.
  • N-methylethanolamine (MMA) is 2.0% by mass
  • Example 7 is 3.0% by mass
  • Example 8 is 4.0% by mass.
  • These are compositions having less amine than the composition ratio (5.0% by mass) of N-methylethanolamine (MMA) in Example 1.
  • the amount of amine in Example 9 is 5.0% by mass, which is the same as the composition ratio of MMA in Example 1.
  • Example 10 is for N-methylethanolamine (MMA) at 6.0% by mass
  • Example 11 is for N-methylethanolamine (MMA) at 7.0% by mass
  • Examples 10 and 12 have compositions with higher amounts of N-methylethanolamine (MMA) than Example 1.
  • Example 1 All the samples of Examples 6 to 11 shown in Table 5 were as good as Example 1 in terms of peel strength, damage to the metal surface, and bath life. That is, even when N-methylethanolamine (MMA) is prepared at a high concentration of 7.0% by mass, there is no problem in performance. That is, in the composition of the present invention, the amine does not have a problem in performance even if it deviates from the prescribed mixing ratio.
  • MMA N-methylethanolamine
  • the resist stripping solution according to the present invention can surely strip a hard-baked resist, and can be suitably used in a situation where a photoresist is used.

Abstract

Dans un procédé de fabrication de dispositifs à semi-conducteurs et similaires, le durcissement est effectué à une température supérieure à celle de l'art antérieur et un durcissement insuffisant des réserves peut être évité. En conséquence, un liquide d'élimination des réserves présentant une force d'élimination supérieure à celle d'un liquide de l'art antérieur est nécessaire.　Le liquide d'élimination des réserves selon l'invention se caractérise en ce qu'il contient: un amine secondaire; 1,3-diméthyl-2-imidazolidinone (DMI) en tant que solvant polaire; de l'eau; ainsi que de l'hydrazine en tant qu'additif; la teneur en eau étant supérieure ou égale à 10,0% en poids et inférieure à 31,0% en poids. Ce liquide permet d'éliminer des réserves cuites à température élevée, sans provoquer de corrosion sur la surface de couche mince ou sur la surface transversale entre autre.
PCT/JP2016/004436 2016-09-30 2016-09-30 Liquide d'élimination des réserves WO2018061064A1 (fr)

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