KR20110019052A - Stripper composition for photoresist or photoresist ashing residue and stripping method of photoresists using the same - Google Patents

Stripper composition for photoresist or photoresist ashing residue and stripping method of photoresists using the same Download PDF

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KR20110019052A
KR20110019052A KR1020090076616A KR20090076616A KR20110019052A KR 20110019052 A KR20110019052 A KR 20110019052A KR 1020090076616 A KR1020090076616 A KR 1020090076616A KR 20090076616 A KR20090076616 A KR 20090076616A KR 20110019052 A KR20110019052 A KR 20110019052A
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photoresist
group
glycol
formula
ashing
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KR1020090076616A
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Korean (ko)
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명중재
유경욱
최경미
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동우 화인켐 주식회사
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents
    • 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
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/029—Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
    • G03F7/0295—Photolytic halogen compounds
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/42—Stripping or agents therefor
    • G03F7/422—Stripping or agents therefor using liquids only
    • G03F7/425—Stripping or agents therefor using liquids only containing mineral alkaline compounds; containing organic basic compounds, e.g. quaternary ammonium compounds; containing heterocyclic basic compounds containing nitrogen

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  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Inorganic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)

Abstract

The present invention relates to an ashing residue stripper composition of a photoresist or a photoresist comprising (A) an amine compound, (B) a naphthalene compound, (C) a glycol-based organic solvent, and (D) water.

Photoresist, peeling, etching, ashing, denaturation

Description

Photoresist or ashing residue peeling liquid composition of photoresist and peeling method using same {STRIPPER COMPOSITION FOR PHOTORESIST OR PHOTORESIST ASHING RESIDUE AND STRIPPING METHOD OF PHOTORESISTS USING THE SAME}

The present invention exposes a photoresist residue, including a cured and / or altered photoresist, remaining on a substrate subjected to etching and ashing during a manufacturing process of a semiconductor device or a flat panel display device to a release liquid composition. The present invention relates to a photoresist or an ashing residue peeling liquid composition of a photoresist which is effectively removed without corrosion of a lower metal film or insulating film, and a peeling method using the same.

In the manufacture of semiconductor devices and flat panel display devices, photoresists are used in the process of forming metal wirings. In addition, a wet or dry ashing process is used to remove the photoresist remaining after the metal wiring is formed through an exposure process. During this ashing process large amounts of photoresist are removed but some photoresist residues may be present. Therefore, it is necessary to remove the photoresist residues, and if the photoresist residues are not removed, it may be a cause of short circuit and disconnection of the wiring in the subsequent process, which may cause a decrease in production yield.

In general, water-soluble organic amines such as monoethanolamine and monoisopropanolamine are widely used to remove photoresist. In order to effectively remove the photoresist, organic solvents such as NMP, gamma butyl lactone and DMSO are used. In addition, in order to suppress corrosion of the metal generated by the amine, various types of corrosion inhibitors such as catechol, resorcinol, benzotriazole are generally used, and a photoresist stripper composition including the same has been proposed.

For example, Korean Patent Laid-Open Publication No. 2005-0040115 discloses a stripping solution containing a water-soluble organic amine compound, an alkylene glycol monoalkyl ether compound, a polar aprotic solvent, and a benzotriazole-based compound as a corrosion inhibitor. In addition, Korean Patent Publication No. 1996-0042177 discloses a release agent comprising an anticorrosive such as amines, water-soluble organic solvents, catechol and benzotriazole. In addition, U.S. Patent No. 5,419,779 discloses monoethanol amine, hydroxyl amine, and catechol as a corrosion inhibitor.

Korean Patent No. 360985 discloses a composition comprising an organic amine compound, an organic solvent, catechol and xylitol as a linear polyhydric alcohol. In addition, Korean Patent Registration No. 503702 contains one or more basic compounds selected from carboxyl group-containing acidic compounds, alkanol amines, and certain quaternary ammonium hydroxides, sulfur-containing anticorrosive agents, and water, and the pH is 3.5-5.5. Photoresist residue strippers are disclosed. Korean Patent Publication No. 2006-0045957 discloses a composition consisting of an amine, a solvent, and a corrosion inhibitor, and the corrosion inhibitor includes a triazole compound, a mercapto compound, and a benzene compound having a hydroxyl group. As described above, the metal corrosion inhibitor is used in a composition containing a basic composition such as a hydroxide composition, an amine or an organic solvent.

When catechol is used as a corrosion inhibitor, good results are obtained in the corrosion protection effect of aluminum, and thus it is widely used in general photoresist stripper compositions. However, in the case of using catechol, problems have been suggested in human health and environmental friendliness due to the carcinogenic harmful effects of catechol, and opinions restricting the use of catechol are suggested. In addition, when the benzotriazole-based compound is used as a corrosion inhibitor, the benzotriazole compound remains on the metal surface and functions as an impurity, which may adversely affect device characteristics. In addition, many problems arise, such as the need to apply a separate cleaning process to remove the benzotriazole-based compound.

As described above, various peeling liquid compositions are known, but it is difficult to find a peeling liquid composition that can sufficiently satisfy the characteristics required by the user.

An object of the present invention is an ashing residue of a photoresist or photoresist that can effectively remove the cured and / or deteriorated photoresist residue by hard baking, plasma etching, high temperature ashing, etc. during the manufacturing process of semiconductor devices and flat panel display devices. It is providing a peeling liquid composition.

SUMMARY OF THE INVENTION An object of the present invention is to provide a photoresist or an ashing residue peeling liquid composition of a photoresist, which is excellent in preventing corrosion of a metal film and an insulating film, and which is harmless to a human body and which can be cleaned by deionized water.

The present invention (A) one or two or more amine compounds selected from the group consisting of a compound represented by the formula (1), a compound represented by the formula (2) and a quaternary amine compound; (B) a compound represented by the following formula (3); (C) glycol-based organic solvents; And (D) water, a photoresist or an ashing residue stripper composition of the photoresist.

<Formula 1>

Figure 112009050606112-PAT00001

<Formula 2>

Figure 112009050606112-PAT00002

<Formula 3>

Figure 112009050606112-PAT00003

In Formulas 1 to 3, R 1 and R 2 are each independently hydrogen, carboxyl group, C 1 ~ C 6 linear or branched alkyl group or C 1 ~ C 6 hydroxyalkyl group, R 3 is C 1 ~ C 6 is a straight or branched chain alkylene group or R 8 OR 9 , R 8 and R 9 are each independently C 1 to C 6 is a straight chain or branched chain alkylene group, and R 4 and R 5 are each independently hydrogen, C 1 to C 6 are straight or branched chain alkyl or alkenyl groups, and R 6 and R 7 are each independently OH or SH.

The present invention also provides a method of forming a photoresist film on a substrate (I); (II) selectively exposing the photoresist film; (III) developing the photoresist film after the exposure to form a photoresist pattern; (IV) etching the substrate using the photoresist pattern as a mask; (V) ashing the photoresist pattern; And (VI) peeling the photoresist residue after the ashing with the photoresist of claim 1 or the ashing residue stripper composition of the photoresist.

The photoresist or the ashing residue stripper composition of the photoresist of the present invention can effectively remove the cured and / or deteriorated photoresist residue by hard baking, plasma etching, high temperature ashing, etc. during the manufacturing process of semiconductor devices and flat panel display devices. Can be. The photoresist of the present invention or the ashing residue peeling liquid composition of the photoresist is excellent in the corrosion preventing effect of the metal film and the insulating film. In particular, the photoresist or the ashing residue peeling liquid composition of the photoresist of the present invention has an excellent corrosion protection effect on aluminum wiring, and thus is effectively used in the manufacturing process of such wiring, and it is easy to clean deionized water and shorten the cleaning time. Can be.

The photoresist peeling composition of the present invention contains (A) an amine compound, (B) a naphthalene compound, (C) a glycol organic solvent, and (D) water.

The (A) amine compound included in the photoresist stripping composition of the present invention is one or two or more selected from the group consisting of a compound represented by the following formula (1), a compound represented by the following formula (2), and a quaternary amine compound. .

<Formula 1>

Figure 112009050606112-PAT00004

<Formula 2>

Figure 112009050606112-PAT00005

In Formulas 1 and 2, R 1 and R 2 are each independently hydrogen, a carboxy group, a C 1 ~ C 6 straight or branched chain alkyl group or C 1 ~ C 6 hydroxyalkyl group, R 3 is C 1 ~ C 6 is a straight or branched chain alkylene group or R 8 OR 9 , R 8 and R 9 are each independently C 1 to C 6 is a straight chain or branched chain alkylene group, and R 4 and R 5 are each independently hydrogen, A C 1 to C 6 straight or branched chain alkyl group or alkenyl group.

The (A) amine compound is preferably included in 1 to 70% by weight based on the total weight of the composition. When included in the above-mentioned range, the removal of photoresist residues is facilitated and the possibility of corrosion of a metal film such as aluminum can be reduced.

Compound represented by the formula (1) is monoethanolamine, diethanolamine, triethanolamine, monopropanolamine, dipropanolamine, tripropanolamine, mono isopropanolamine, diisopropanolamine, triisopropanolamine, butanolamine, butyl mono It is preferable that it is 1 type, or 2 or more types chosen from the group which consists of ethanolamine, ethyl diethanolamine, N -methylamino ethanol, and N -acetylethanolamine.

The compound represented by the formula (2) is preferably one or two or more selected from the group consisting of hydroxyamine, tetramethylhydroxyamine and tetrabutylhydroxyamine.

The quaternary amine compound is preferably one or two or more selected from the group consisting of tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide and tetrabutylammonium hydroxide.

(B) naphthalene type compound contained in the photoresist peeling composition of this invention is represented by General formula (3). (B) It is used as a corrosion inhibitor which suppresses corrosion of a naphthalene type environmentally friendly metal film.

<Formula 3>

Figure 112009050606112-PAT00006

In Formula 3, R 6 and R 7 are each independently OH or SH.

The compound represented by Formula (B) 3 is preferably included in 0.1 to 20% by weight based on the total weight of the composition. If the above range is satisfied, the corrosion preventing effect of the metal film can be sufficiently exhibited.

The compound represented by the formula (3) is a compound having two or more hydroxyl groups or thiol groups, and having two aromatic rings, a non-covalent electron pair of oxygen of the hydroxy group or a non-covalent electron pair of the thiol group sulfur and a metal It can be expected to have the effect of chelating by action, and can be expected to be applied on the metal surface. In addition, an additional chelate effect can be expected by electrons of double bonds in aromatics. When the compound represented by the formula (3) is applied on the metal surface, the effect of suppressing the interaction between the amine and the metal appears, it can be expected that the corrosion of the metal by the amine is reduced. In addition, in order to more effectively reduce the corrosiveness of the metal, it is preferable to use a compound capable of more smoothly bonding between the oxygen of the hydroxy group or the sulfur element of the thiol group and the metal, and a chemical formula having two hydroxy or thiol groups More preferable effects can be expected from the compound represented by 3.

The compound represented by the formula (B) is 1,3-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 2,3 1 or 2 or more types selected from the group consisting of -dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1,8-dithionaphthalene, 2,6-dithionaphthalene and 2,7-dithionaphthalene It is preferable.

The (C) glycol-based organic solvent included in the photoresist or ash residue of the photoresist stripping composition of the present invention assists in removing the photoresist and controls the activity of the amine to prevent corrosion of the metal by the amine. It can help.

The (C) glycol-based organic solvent is preferably included in 5 to 50% by weight based on the total weight of the composition. If the above range is satisfied, it may help to remove the photoresist, and may help to prevent the corrosiveness of the metal by the amine by controlling the activity of the amine.

The organic solvents (C) glycols are ethylene glycol, propylene glycol, diethylene glycol monobutyl ether, tetraethylene glycol, triethylene glycol, tetraethylene glycol, trimethylene glycol, diethylene glycol, beta butylene glycol, butyl diglycol And it is preferable that it is 1 type, or 2 or more types chosen from the group which consists of methyl diglycol.

Although the (D) water contained in the photoresist of this invention or the ashing residue peeling liquid composition of a photoresist is not specifically limited, It is preferable to use deionized water whose specific resistance value is 18 MPa / cm or more as water for a semiconductor process. . The water (D) is included in the balance so that the total weight of the composition is 100% by weight.

The photoresist or ashing residue stripper composition of the photoresist of the present invention may further comprise conventional additives known in the art to improve the stripping performance of the photoresist residue.

The components included in the stripper composition of the present invention can be prepared according to conventionally known methods, and it is particularly preferable to have a purity for semiconductor processing. The pH of the photoresist prepared by the present invention or the ashing residue stripper composition of the photoresist is preferably adjusted to 7-13. When the pH of the photoresist or the ashing residue peeling liquid composition of the photoresist is included in the above range, the effect of removing the photoresist residue is excellent, and the fear of corrosion of the metal film due to the strong basicity can be avoided.

The photoresist of the present invention or the ashing residue stripper composition of the photoresist may be prepared by advantageously mixing the above-mentioned compounds in a predetermined amount, and the mixing method is not particularly limited and various known methods may be applied.

The photoresist or ashing residue stripper composition of the photoresist of the present invention comprises a hard baking, plasma etching, hardening and / or altered photoresist in the manufacturing process of a semiconductor device or a flat panel display device. It can be used in a stripping process that effectively removes photoresist residues.

The photoresist or ashing residue stripper composition of the present invention effectively removes photoresist residues by increasing the activity of the compounds in the composition in a water base. In addition, the photoresist or the ashing residue peeling liquid composition of the photoresist of the present invention can be applied to both a batch method of peeling a plurality of wafers at once or a single wafer processor method of peeling one sheet at a time.

The present invention also provides a method of forming a photoresist film on a substrate (I); (II) selectively exposing the photoresist film; (III) developing the photoresist film after the exposure to form a photoresist pattern; (IV) etching the substrate using the photoresist pattern as a mask; (V) ashing the photoresist pattern; And (VI) peeling the photoresist residue after the ashing with the stripper composition of the present invention.

In addition, the present invention comprises the steps of performing a dry etching process or a chemical mechanical polishing (CMP) process without performing a photoresist pattern forming process using a (i) mask; And (ii) peeling the photoresist residue exposed by the above process into the stripper composition of the present invention.

Formation, exposure, development, etching and ashing of the photoresist film in the peeling method can be carried out by methods commonly known in the art and are not particularly limited. A good peeling result can be obtained as long as the substrate in which the photoresist residue including the photoresist cured or modified with polymer is present can be brought into contact with the stripper composition.

As the peeling method, a deposition method, a spraying method, or a deposition and spraying method may be used. When peeling by deposition, spraying, or spraying and spraying, as the peeling conditions, the temperature is usually 10 to 100 ° C, preferably 20 to 80 ° C, and the deposition, spraying, or deposition and spraying time is usually 30 seconds to 40 minutes. , Preferably it is 1 to 20 minutes. However, these conditions are not strictly applied and can be modified to suitable conditions by those skilled in the art.

Hereinafter, the present invention will be described in detail through examples. However, the following examples and the like are provided to explain the present invention in more detail, and the scope of the present invention is not limited thereto.

Examples 1 to 10 and Comparative Examples 1 to 3: Photoresist or Ashing Residue Stripping Composition of Photoresist

By mixing the composition and content as shown in Table 1 below to prepare the photoresist or the ashing residue peeling liquid composition of the photoresist of Examples 1 to 10 and Comparative Examples 1 to 3.

Compound represented by formula (1)
(weight%) Compound represented by formula (2)
(weight%) Quaternary amine compound (% by weight) Compound represented by Formula 3 (% by weight) Glycol Organic Solvents
(weight%) water
(weight%) Example 1 MEA 30 - - - - A-1 10 - - Balance Example 2 MEA 45 - - TMAH 5 A-1 5 EG 15 Balance Example 3 MEA 30 - - TMAH 5 A-1 10 EG 25 Balance Example 4 MEA 45 HA 3 TMAH 8 A-2 5 EG 25 Balance Example 5 MEA 30 - - TMAH 6 A-2 7 BDG 25 Balance Example 6 MIPA 45 HA 4 TMAH 8 A-2 15 BDG 15 Balance Example 7 MEA 10 HA 4 TMAH 10 A-2 5 EG 35 Balance Example 8 - - HA 4 TMAH 10 A-2 5 BDG 35 Balance Example 9 MEA 30 HA 4 TMAH 6 A-2 5 BDG 20 Balance Example 10 MEA 35 HA 4 - - A-2 10 BDG 25 Balance Comparative Example 1 MEA 45 HA 4 TMAH 10 - - - - Balance Comparative Example 2 MEA 45 HA 4 - - - - - - Balance Comparative Example 3 - - HA 4 TMAH 15 - - - - Balance

MEA: monoethanolamine

MIPA: monoisopropanolamine

TMAH: tetramethylammonium hydroxide

HA: hydroxylamine

A-1: 2,7-dihydroxynaphthalene

A-2: 2,3-dihydroxynaphthalene

EG: ethylene glycol

BDG: Butyl diglycol

Test Example: Characterization of Photoresist or Ash Residue Stripping Liquid Composition of Photoresist

Peelability and Corrosion Test

After the plasma etching or high temperature ashing, the photoresist residues and the polymer residues of the deteriorated photoresist and the SiO 2 insulating film attached to the insulating film and the substrate having the Al metal wiring were separated from the stripping solution having a temperature of 65 ° C (Examples 1 to 10 and comparison). After immersing in each of Examples 1-3 for 20 minutes, the specimen was taken out from the stripping solution, rinsed with ultrapure water for 1 minute, and dried using nitrogen gas. In addition, the scanning electron microscope was used to evaluate the removability (peelability) of the photoresist residue and polymer remaining after dry etching or high temperature ashing from the substrate having the SiO 2 insulating film and the Al metal wiring, and the corrosion resistance of the Al metal wiring. . Peelability and anticorrosive evaluation were evaluated based on the following criteria. The results are shown in Table 2 below.

Peelability Evaluation Criteria

◎: very good, ○: good, Δ: some residue present, X: residue not removable

[Al anticorrosive evaluation criteria]

◎: no corrosion, ○: almost no corrosion, △: partial corrosion, surface roughness change, X: etching

Peelability Al anticorrosive Example 1 ○ ◎ Example 2 ○ ○ Example 3 ◎ ◎ Example 4 ◎ △ Example 5 ○ ○ Example 6 ◎ ◎ Example 7 ○ ○ Example 8 ○ ◎ Example 9 ◎ ◎ Example 10 ○ ◎ Comparative Example 1 ◎ X Comparative Example 2 ◎ X Comparative Example 3 ◎ X

Referring to Table 2, it was confirmed that the peeling liquid compositions of Examples 1 to 10 had good photoresist residue peelability and corrosion resistance to aluminum.

Claims (9)

(A) one or two or more amine compounds selected from the group consisting of a compound represented by the following formula (1), a compound represented by the following formula (2) and a quaternary amine compound; (B) a compound represented by the following formula (3); (C) glycol-based organic solvents; And (D) The ashing residue peeling liquid composition of the photoresist or photoresist characterized by including water. <Formula 1>
Figure 112009050606112-PAT00007
 <Formula 2>
Figure 112009050606112-PAT00008
 <Formula 3>
Figure 112009050606112-PAT00009
 In Chemical Formulas 1 to 3, R 1 and R 2 are each independently hydrogen, a carboxy group, a C 1 to C 6 straight or branched chain alkyl group or a C 1 to C 6 hydroxyalkyl group, R 3 is a C 1 to C 6 straight or branched alkylene group or R 8 OR 9 , and R 8 and R 9 are each independently a C 1 to C 6 straight or branched alkylene group, R 4 and R 5 are each independently hydrogen, a straight or branched chain alkyl group or alkenyl group having 1 to 6 carbon atoms, R 6 and R 7 are each independently OH or SH. The method according to claim 1, Regarding the total weight of the composition, 1 to 70% by weight of the (A) amine compound; 0.1 to 20% by weight of the compound represented by Formula (B); 5 to 50% by weight of the (C) glycol-based organic solvent; And The ashing residue peeling liquid composition of the photoresist or photoresist containing the said (D) residual amount of water. The method according to claim 1, The compound represented by the formula (1) is monoethanolamine, diethanolamine, triethanolamine, monopropanolamine, dipropanolamine, tripropanolamine, mono isopropanolamine, diisopropanolamine, triisopropanolamine, butanolamine, butyl monoethanolamine Eshing residue peeling liquid composition of a photoresist or photoresist, characterized in that one or two or more selected from the group consisting of ethyl diethanolamine, N -methylaminoethanol and N -acetylethanolamine. The method according to claim 1, The compound represented by the formula (2) is one or more selected from the group consisting of hydroxylamine, tetramethylhydroxylamine and tetrabutyl hydroxylamine or ashing residue peeling solution of the photoresist, characterized in that Composition. The method according to claim 1, The quaternary amine compound is one or two or more selected from the group consisting of tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide and tetrabutylammonium hydroxide. Or ashing residue stripper composition of a photoresist. The method according to claim 1, The compound represented by the formula (B) is 1,3-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 1,6-dihydroxynaphthalene, 1,7-dihydroxynaphthalene, 2,3 1 or 2 or more types selected from the group consisting of -dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1,8-dithionaphthalene, 2,6-dithionaphthalene and 2,7-dithionaphthalene An ashing residue stripper composition of a photoresist or photoresist, characterized in that. The method according to claim 1, The glycol-based organic solvent is ethylene glycol, propylene glycol, diethylene glycol monobutyl ether, tetraethylene glycol, triethylene glycol, tetraethylene glycol, trimethylene glycol, diethylene glycol, beta butylene glycol, butyl diglycol and methyl di A photoresist or an ashing residue stripper composition of a photoresist, characterized in that it comprises one or two or more selected from the group consisting of glycols. The method according to claim 1, The ashing residue peeling liquid composition of the photoresist or photoresist, characterized in that the pH of the ashing residue peeling liquid composition of the photoresist or photoresist is 7 to 13. (I) forming a photoresist film on the substrate; (II) selectively exposing the photoresist film; (III) developing the photoresist film after the exposure to form a photoresist pattern; (IV) etching the substrate using the photoresist pattern as a mask; (V) ashing the photoresist pattern; And (VI) peeling the photoresist residue after the ashing with the photoresist of claim 1 or the ashing residue peeling liquid composition of the photoresist.
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KR101323040B1 (en) * 2012-03-16 2013-10-29 주식회사 케이씨텍 Cleaning solution composition and the cleaning method therewith

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101323040B1 (en) * 2012-03-16 2013-10-29 주식회사 케이씨텍 Cleaning solution composition and the cleaning method therewith

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