Classifications

• • 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
• • D—TEXTILES; PAPER
  • D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
  • D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
  • D04H13/00—Other non-woven fabrics
• • B—PERFORMING OPERATIONS; TRANSPORTING
  • B32—LAYERED PRODUCTS
  • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
  • B32B27/00—Layered products comprising a layer of synthetic resin
  • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
  • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
  • C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
  • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
  • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
  • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
  • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Definitions

• the present invention relates to a removing composition for removing resists in a photo-lithography process. More particularly, the present invention relates to a removing composition which can minimize corrosion of the metallic circuitry during the resist removal process when it is used for the process of patterning the metallic circuitry and has an excellent ability to remove resist.
• Photo-resist is an essential material used in the photo-lithography process, and the photo-lithography process is one of the general processes used to manufacture semiconductor devices such as integrated circuits (IC), large scale integration (LSI), very large scale integration (VLSI) and image display devices such as liquid crystal displays (LCD) and plasma display devices (PDP).
• the present invention provides a resist remover composition containing amine and protonic polar solvent, where the amine is a cyclic amine compound. Further, the present invention provides a resist remover composition containing amine and aprotonic polar solvent, where the amine is a cyclic amine compound. Further, the present invention provides a resist remover composition containing amine, protonic polar solvent, and aprotonic polar solvent, where the amine is a cyclic amine compound.
• the resist remover composition of the present invention has outstanding ability to remove resist, and has the effect of completely removing and washing away resist without undesirable corrosion of the metal wire which arises during the process, while providing stability to the process due to little change in the composition by volatilization during heating. Best Mode Hereinafter is given a detailed description of the present invention. It was discovered that utilization of amine and solvent which doesn't have an effect on corrosion of metal wire prevents corrosion of the bottom film due to Galvanic coupling with the upper metal film and eliminates resist effectively at the same time. Therefore, the resist remover composition can minimize corrosion of the metallic circuitry during the resist removal process when it is used for the process of patterning the metallic circuitry and has an excellent ability of resist removal.
• Such a resist remover composition of the present invention contains amine and solvent, where the amine is a cyclic amine compound.
• the composition of the present invention is a two or three-component composition of protonic polar solvent or aprotonic polar solvent individually or a mixture of one or more thereof.
• resist removing composition of the present invention is a two-component compound containing the cyclic amine and protonic polar solvent, or it can be a two-component compound containing the cyclic amine and aprotonic polar solvent. It can also be a three-component compound containing the cyclic amine and both protonic polar and aprotonic polar solvents.
• this cyclic amine compound could cause to break the attractive force in intra or inter-molecules by penetrating the crosslinked resist polymer matrix transformed under various processes such as dry etching or wet etching, and ashing or ion implant processing.
• This reaction caused by amine compound helps to remove resist attached onto the substrate plate by transforming the remaining resist to an amorphous polymer gel mass by forming empty internal space in structurally weak areas of the resist.
• the cyclic amine used in the present invention has high boiling point so that it does not undergo significant changes in its weight or composition, and shows similar removal ability of previous open chain amines, and can be utilized for longer during the treatment process.
• the cyclic amine compounds can be one or more compound selected from the group consisting of in [Chemical Formula 1] below .
• R-i is C-i to C 5 alkyl, or C ⁇ to C 5 allyl
• R 2 and R 3 are each independently or simultaneously C-, to C 5 alkyl, d to C 5 allyl, C 1 to C 5 alkyl amino, C-i to C 5 hydroxyl alkyl(alkyl alcohol), or d to C 5 alkyl benzene.
• the cyclic amine is a piperazine group or a morpholine group compound.
• the cyclic amine compounds is one or more compounds selected from the group consisting of 1-(2-hydroxy ethyl)piperazine(1-1), 1 -(2-aminoethyl)piperazine(1 -2), 1 -(2-hydroxyethyl)-4-methyl(1 -3)piperazine, and N-(3-aminopropyl)morpholine(1 -4), 2-methylpiperazine(1 -5),
• both two-component and three-component compositions it is preferable for both two-component and three-component compositions to contain 5 to 30 wt% of the total composition, because if the content of amine is below 5 wt%, the resist-removal ability decreases. If the content of amine exceeds 30 wt%, the corrosion problem can become worse.
• the protonic polar solvent is preferably one or more glycolether compounds seleted from the group consisting of ethyleneglycol methylether, ethyleneglycol ethylether, ethyleneglycol butylether, diethyleneglycol methylether, diethyleneglycol ethylether, diethyleneglycol butylether, and diethyleneglycol propylether.
• glycolether solvent with boiling point above 180 ° C and almost unlimited solubility in water. Diethyleneglycol methylether, diethyleneglycol butylether, and diethyleneglycol ethylether would be most appropriate.
• glycolether solvent with boiling point above 180 ° C could minimize the change in removal ability due to change in composition.
• This glycolether solvent does not volatilize much so that it maintains its initial composition. Thus, it maintains the ability to remove resist throughout the whole process.
• the glycolether solvent with boiling point above 180 °C can improve removal efficacy of resist because of its low surface force on metal film layer and resist, and due to its low freezing point and high combustion point, it is more stable during storage.
• the protonic polar solvent with 70 to 95 wt% of total composition it is preferable to use the protonic polar solvent with 70 to 95 wt% of total composition.
• the content is below 70 wt%, corrosion occurs excessively because of the increase of amine content, and resist removal performance declines if the content exceeds 95 wt%.
• the protonic polar solvent at 10 to 80 wt%. Below 10 wt %, the weight percentage of aprotonic polar solvent and amine compound is relatively increased, which causes excessive corrosion of metal wire and decreases the resist removal ability because of the deficiency in ability to dissolve the polymer gel created by the amine compound and aprotonic polar solvent.
• the present invention establishes the role of aprotonic polar solvent to dissolve exfoliated high polymer gel mass into unit molecules. Especially, it can prevent re-adhesion of removed resist that commonly occurs during the washing process.
• Polar solvent with amine as the functional group like
• N-methyl-2-pyrrolidone assists the amine compound penetrate and remove resist.
• the aprotonic polar solvent is one or more compounds selected from the group consisting of . N-methyl-2-pyrrolidone, N,N-dimethylacetamide, N,N-dimethyformamide, and N,N-dimethylimidazole.
• a content of aprotonic polar solvent that is 70 to 95 wt% of the total composition. If the content is below 70 wt%, corrosion occurs excessively because of the increase of amine constituent, and removal performance diminishes under the condition of its content over 95 wt%.
• the content of aprotonic polar solvent would preferably be 15 to 70 wt% of the total composition. Its content less than 15 wt% would decrease the resist removal ability. If it exceeds 70 wt%, metal wire is excessively corroded, and its potential to remove and wash resist decreases because of the relative decrease in weight % of glycolether, a protonic polar solvent.
• the present invention defines composition comprising cyclic amine for resist removal during use in photo-lithography, which shows excellent ability to remove resist and minimize the problem of patterned metal wire corrosion.
• the specimen n+a-Si:H active film
• Chrome maximizes adhesive strength of resist
• dry etching gas transforms resist into a form that is difficult to remove with removal solution.
• the specimen is suitable for testing the ability of resist removal.
• Size of specimen is 2cm x 4cm Specimen for Experiment 4 (2) Apply aluminum, molybdenum, and copper on the glass plate with 2000 A thickness. Size of specimen is 2cm x 4cm With the prepared specimen above, the experiment was performed with 17 different compositions of removal solution. Table 4
• APM N-(3-aminopropyl)morpholine
• HEMP 1-(2- hydroxyethyl)-4-methylpiperazine
• Table 5 shows that compositions containing 1-(2-hydroxyethyl)piperazine have do not remove resist well, while other cyclic amines are as good as open chain amines in their ability to exfoliate.
• 1-(2-hydroxyethyl)-4-methylpiperazine is a tertiary amine where all the hydrogens of the -N- group are substituted by other functional groups, and it can be seen that even in the cyclic amines, tertiary amines are not good at exfoliating as in the case of open chain amines.
• Example 16 resist removal is not achieved because the activity of amine in the removal solution is low, and no corrosion is observed while resist is not removed.
• Example 16 resist removal is not achieved because the activity of amine in the removal solution is low, and no corrosion is observed while resist is not removed.
• 1-(2-aminoethyl) piperazine or N-(3-aminopropyl)morpholine is used, corrosion of copper is observed, and the structure of the compounds are cyclic amines containing primary amine.
• the cyclic amines that performed well for all three metals do not contain primary amine, and are mostly secondary or tertiary amine structures.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
• Photosensitive Polymer And Photoresist Processing (AREA)
• Cleaning Or Drying Semiconductors (AREA)

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• 2004
  • 2004-05-07 KR KR1020040032112A patent/KR101082018B1/ko active IP Right Grant
• 2005
  • 2005-05-06 CN CNA2005800145635A patent/CN1950754A/zh active Pending
  • 2005-05-06 WO PCT/KR2005/001326 patent/WO2005109107A1/en active Application Filing
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