[go: up one dir, main page]

CN107239006B - Resist stripping liquid composition, flat plate, method for manufacturing flat plate, and display device - Google Patents

Resist stripping liquid composition, flat plate, method for manufacturing flat plate, and display device Download PDF

Info

Publication number
CN107239006B
CN107239006B CN201610916985.1A CN201610916985A CN107239006B CN 107239006 B CN107239006 B CN 107239006B CN 201610916985 A CN201610916985 A CN 201610916985A CN 107239006 B CN107239006 B CN 107239006B
Authority
CN
China
Prior art keywords
resist
resist stripping
liquid composition
bis
chemical formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201610916985.1A
Other languages
Chinese (zh)
Other versions
CN107239006A (en
Inventor
高京俊
金正铉
崔汉永
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dongwoo Fine Chem Co Ltd
Original Assignee
Dongwoo Fine Chem Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dongwoo Fine Chem Co Ltd filed Critical Dongwoo Fine Chem Co Ltd
Publication of CN107239006A publication Critical patent/CN107239006A/en
Application granted granted Critical
Publication of CN107239006B publication Critical patent/CN107239006B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/04—Saturated ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C07C43/164—Unsaturated ethers containing six-membered aromatic rings
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements

Landscapes

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

Abstract

The invention relates to a resist stripping liquid composition, a flat plate for a display device, a manufacturing method thereof and a display device. The resist stripping liquid composition comprises (a) a compound represented by the following chemical formula 1 and (b) an alkali compound, and optionally further comprises (c) other components except the component (a) and the component (b). In the following chemical formula 1, n is an integer of 1-3; r1And R2Each independently hydrogen, C1-C10 alkyl, or a group containing 1-5 oxygen atoms and 2-10 carbon atoms, wherein the oxygen atoms and the carbon atoms form an ether bond; r3And R4Is absent or is independently C1-C5 alkoxy; aryl of C6-C12; aryloxy of C6 to C12 substituted or unsubstituted with amino or alkyl of C1 to C5; a hydroxyl group; -CN; or an amino group. [ chemical formula 1]

Description

Resist stripping liquid composition, flat plate, method for manufacturing flat plate, and display device
Technical Field
The present invention relates to a resist stripping liquid composition, a method for manufacturing a flat panel for a display device using the stripping liquid, a flat panel for a display device manufactured by using the method, and a display device including the flat panel.
Background
As the demand for high resolution presentation of flat panel display devices has increased in recent years, efforts to increase pixels per unit area are continuously being made. In response to such a trend, a reduction in the width of the wiring is also required, and in order to meet such a requirement, a dry etching process or the like is introduced, so that process conditions are becoming more and more severe.
Further, since signal speed in the wiring is also required to be increased due to the upsizing of the flat panel display device, copper having a lower resistivity than aluminum is put to practical use as a wiring material. Accordingly, the performance required of the stripping solution used in the stripping step as a resist removal step has also increased.
Specifically, the peeling characteristics are required to be in a suitable level for the removal force of the etching residue generated after the dry etching step, the corrosion inhibition force for the metal wiring, and the like. In particular, corrosion inhibition of aluminum and copper is also required, and in order to ensure price competitiveness, economical efficiency such as an increase in the number of processed substrates is also required.
In response to such a demand, new technologies have been developed. For example, korean laid-open patent No. 2012-0055449 discloses a photoresist stripper composition using glycol ethers and acetates as additives. The above-mentioned techniques are characterized in that glycol ethers and acetates are used as additives and solvents.
However, some glycol ethers having a low boiling point volatilize in a large amount in the process, and thus increase the process Loss (Loss), and the acetate esters react with the organic amine and the alkali compound, which are basic components of the stripper, and thus have a disadvantage that it is difficult to ensure the performance of the photoresist stripper.
Documents of the prior art
Patent document
Korean laid-open patent No. 2012-0055449
Disclosure of Invention
Problems to be solved
The present invention has been made to solve the above-mentioned problems of the conventional techniques, and an object of the present invention is to provide a resist stripping solution composition which is excellent in removal ability of resist patterns and dry and wet etching residues, does not volatilize in a stripping step, and does not remain after the stripping step.
Another object of the present invention is to provide a method for manufacturing a flat panel for a display device using the stripping liquid composition, a flat panel for a display device manufactured by the method, and a display device including the flat panel.
Means for solving the problems
In order to achieve the above object, the present invention provides a resist stripping liquid composition comprising (a) a compound represented by the following chemical formula 1 and (b) a base compound, and optionally further comprising (c) another component other than the above (a) and (b),
[ chemical formula 1]
Figure BDA0001134991420000021
In the formula, n is an integer of 1-3;
R1and R2Each independently hydrogen, C1-C10 alkyl, or a group containing 1-5 oxygen atoms and 2-10 carbon atoms, wherein the oxygen atoms and the carbon atoms form an ether bond;
R3and R4Is absent or is independently C1-C5 alkoxy; aryl of C6-C12; aryloxy of C6 to C12 substituted or unsubstituted with amino or alkyl of C1 to C5; a hydroxyl group; -CN; or an amino group.
The present invention also provides a method for producing a flat panel for a display device, comprising a step of stripping a resist of a flat panel substrate using the resist stripping liquid composition.
The present invention also provides a flat panel for a display device, which is manufactured by the method for manufacturing a flat panel for a display device.
In addition, the invention provides a flat panel display device, which is characterized by comprising the flat panel.
Effects of the invention
The resist stripping liquid composition of the invention has the following characteristics: in the manufacturing process of the flat panel display, the resist pattern and the etching residue are effectively removed without volatilization, and are not left after the stripping process. In addition, it has excellent cumulative processed sheet number characteristics.
Further, a flat plate for a display device manufactured using the stripping liquid composition and a display device including the flat plate have desirable element characteristics.
Detailed Description
Hereinafter, the present invention will be described with respect to each constituent element centering on the operation.
The present invention relates to a resist stripping liquid composition comprising (a) a compound represented by the following chemical formula 1 and (b) a base compound, and optionally further comprising (c) another component other than the above-mentioned component (a) and component (b),
[ chemical formula 1]
Figure BDA0001134991420000031
In the formula, n is an integer of 1-3;
R1and R2Each independently hydrogen, C1-C10 alkyl, or a group containing 1-5 oxygen atoms and 2-10 carbon atoms, wherein the oxygen atoms and the carbon atoms form an ether bond;
R3and R4Is absent or is independently C1-C5 alkoxy; aryl of C6-C12; aryloxy of C6 to C12 substituted or unsubstituted with amino or alkyl of C1 to C5; a hydroxyl group; -CN; or an amino group.
The resist stripping liquid composition comprises (a) 10 to 99.9 wt% of one or more compounds represented by the chemical formula 1, (b) 0.1 to 20 wt% of an alkali compound, and (c) 0 to 70 wt% of other components, based on the total weight of the composition.
When the other component (c) is one or more selected from the group consisting of a water-soluble polar solvent and water, the composition may contain 10 to 98 wt% of the compound represented by the formula 1 (a), 0.1 to 20 wt% of the alkali compound (b), and the balance of one or more selected from the group consisting of a water-soluble polar solvent and water as the other component (c), based on the total weight of the composition.
In the present invention, the term "selectively" means that other components may be optionally contained or that other components may not be further contained.
The resist stripping solution composition of the present invention may further comprise one or more components selected from the group consisting of water-soluble polar solvents and water as the other component (c) above.
Hereinafter, each constituent component will be described in detail:
(a) one or more compounds represented by chemical formula 1
The compound represented by the above chemical formula 1 acts as a water-soluble solvent to dissolve the resist polymer, does not remain on the substrate during the rinsing process with deionized water after the stripping, and has a high boiling point of 150 ℃ or higher, so that the stripping solution can be prevented from being volatilized and lost during the stripping process.
The compound represented by the above chemical formula 1 may preferably be selected from the group consisting of bis (2-ethoxyethoxy) methane, bis (2-methoxyethoxy) methane, bis (2-butoxyethoxy) methane, 1, 13-diethoxy-3, 6,8, 11-tetraoxa-tridecane, 1, 13-dimethoxy-3, 6,8, 11-tetraoxa-tridecane, formaldehyde [ bis- (2-phenoxyethyl) acetal ] (formaldehydehyde [ bis- (2-phenoxyethyl) acetic ]), 4- (2- ((2-ethoxyethoxy) methoxy) ethoxy) aniline, formaldehyde [ bis (2-o-tolyloxyethyl) acetal ], 2,4,7,9,12, 14-hexaoxapentadecane, 3,6,9,12,15,18,21, 24-octaoxapentacanol, formaldehyde [ bis (2-isopropoxyethyl) acetal ], 4 '- (2, 2' -methylenebis (oxy) bis (ethane-2, 1-diyl) bis (oxy)) diphenylamine, 4,7,9,12,14, 17-hexaoxaeicosane-1, 20-dinitrile (4,7,9,12,14, 17-hexaoxaeicosane-1, 20-dinitrile), 1-phenyl-2, 5,7, 10-tetraoxaundecane, 3,6,8, 11-tetraoxatridecane-1, 13-diamine, and the like.
The compound represented by the above chemical formula 1 may be 10 to 99.9 wt% with respect to the total weight of the composition.
When the amount of the compound represented by chemical formula 1 is less than 10% by weight, the solubility of the compound to the photoresist to be removed may be lowered, and when the amount exceeds 99.9%, the removal property of the photoresist may be lowered or the metal film may be corroded due to the absence of other components.
(b) Alkali compound
The alkali compound effectively penetrates into a modified or crosslinked resist (resist) polymer matrix under various process conditions such as dry or wet etching, ashing (ashing), ion implantation (ion implantation), etc., thereby breaking intramolecular or intermolecular bonds, and thus forming a space in a structurally fragile portion of the resist remaining on the substrate to deform the resist into an amorphous polymer gel (gel) bulk state, thereby easily removing the resist adhering to the upper portion of the substrate.
The alkali compound preferably includes KOH, NaOH, TMAH (Tetramethylammonium hydroxide), TEAH (tetraethylammonium hydroxide), carbonates, phosphates, ammonia, amines, and the like, and one or more of these may be used alone or in combination.
Examples of the amines include primary amines such as methylamine, ethylamine, monoisopropylamine, n-butylamine, sec-butylamine, isobutylamine, tert-butylamine, and pentylamine; secondary amines such as dimethylamine, diethylamine, dipropylamine, diisopropylamine, dibutylamine, diisobutylamine, methylethylamine, methylpropylamine, methylisopropylamine, methylbutylamine, and methylisobutylamine; tertiary amines such as diethylhydroxylamine, trimethylamine, triethylamine, tripropylamine, tributylamine, tripentylamine, dimethylethylamine, methyldiethylamine, and methyldipropylamine; alkanolamines such as choline, monoethanolamine, diethanolamine, triethanolamine, monopropanolamine, 2-aminoethanol, 2- (ethylamino) ethanol, 2- (methylamino) ethanol, N-methyldiethanolamine, N-dimethylethanolamine, N-diethylaminoethanol, 2- (2-aminoethylamino) -1-ethanol, 1-amino-2-propanol, 2-amino-1-propanol, 3-amino-1-propanol, 4-amino-1-butanol, and dibutanolamine; alkoxyamines such as (butoxymethyl) diethylamine, (methoxymethyl) dimethylamine, (butoxymethyl) dimethylamine, (isobutoxymethyl) dimethylamine, (methoxymethyl) diethanolamine, (hydroxyethyloxymethyl) diethylamine, methyl (methoxymethyl) aminoethanol, methyl (butoxymethyl) aminoethanol, and diglycolamine; and cyclic amines having a ring formed, such as hydroxyethylpiperazine, 1- (2-aminoethyl) piperazine, 1- (2-hydroxyethyl) methylpiperazine, N- (3-aminopropyl) morpholine, 2-methylpiperazine, 1-amino-4-methylpiperazine, 1-benzylpiperazine, 1-phenylpiperazine, N-methylmorpholine, 4-ethylmorpholine, N-formylmorpholine, N- (2-hydroxyethyl) morpholine, and N- (3-hydroxypropyl) morpholine.
The alkali compound may be present in an amount of 0.1 to 20 wt%, preferably 1 to 15 wt%, and more preferably 2 to 10 wt%, based on the total weight of the composition. When the alkali compound is less than 0.1 wt%, the problem of reduction in resist stripping force occurs, and when the alkali compound exceeds 20 wt%, the corrosion rate of the metal wiring made of aluminum or an aluminum alloy and copper or a copper alloy is rapidly increased.
(c) Other ingredients
Water-soluble polar solvent
The resist stripping solution composition of the present invention may further comprise a water-soluble polar solvent. The water-soluble polar solvent plays a role of dissolving the gelled resist polymer together with the compound represented by the chemical formula 1, and further, allows smooth removal of the stripping solution using water in a rinsing process of deionized water after resist stripping, minimizing re-adsorption/re-adhesion of the stripping solution and the dissolved resist.
The water-soluble polar solvent includes a protic polar solvent and an aprotic polar solvent excluding the polyhydric alcohol, and they may be used alone or in a mixture thereof.
Preferable examples of the protic polar solvent include alkylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol monoisopropyl ether, triethylene glycol monobutyl ether, polyethylene glycol monomethyl ether, polyethylene glycol monobutyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, and tripropylene glycol monomethyl ether, and tetrahydrofurfuryl alcohol, and one kind or two or more kinds of these may be used alone or in combination.
Preferable examples of the aprotic polar solvent include pyrrolidone compounds such as N-methylpyrrolidone (NMP) and N-ethylpyrrolidone; imidazolidinone compounds such as 1, 3-dimethyl-2-imidazolidinone and 1, 3-dipropyl-2-imidazolidinone; lactone compounds such as γ -butyrolactone; sulfoxide compounds such as dimethyl sulfoxide (DMSO) and sulfolane; phosphate compounds such as triethyl phosphate and tributyl phosphate; carbonate compounds such as dimethyl carbonate and ethylene carbonate; amide compounds such as formamide, N-methylformamide, N-dimethylformamide, acetamide, N-methylacetamide, N-dimethylacetamide, N- (2-hydroxyethyl) acetamide, 3-methoxy-N, N-dimethylpropionamide, 3- (2-ethylhexyloxy) -N, N-dimethylpropionamide, and 3-butoxy-N, N-dimethylpropionamide, which may be used alone or in combination of two or more.
The above-mentioned water-soluble polar solvent is preferably not too high or too low in boiling point to achieve an appropriate peeling force, and may be used mixedly. The water-soluble polar solvent may be added in the peeling step according to further required performance, and may be 5 to 80% by weight.
Water (W)
The resist stripping solution composition of the present invention may further comprise water. The water performs the following functions: the activity of the alkali compound is improved, the stripping speed is increased, and organic contaminants and resist stripping liquid remaining on the substrate are quickly and completely removed in the rinsing process using deionized water.
As the water, deionized water can be preferably used.
The amount of the water is preferably 0.1 to 70 wt%, more preferably 20 to 45 wt% or less. If the water content exceeds 70 wt%, the dissolution capacity of the resist may be reduced to reduce the number of processed sheets, and corrosion of metal wiring may be caused when the substrate is immersed for a long time.
The specific composition ratio of each embodiment of the resist stripping liquid composition of the present invention can be set as follows:
(1) in the case where the above-described components include only (a) the compound represented by chemical formula 1 and (b) the alkali compound, the resist stripping composition of the present invention may include 80 to 99.9 wt% of the compound represented by chemical formula 1 and 0.1 to 20 wt% of the alkali compound, based on the total weight of the composition.
(2) In the case where the resist stripping composition of the present invention contains (a) the compound represented by chemical formula 1, (b) the alkali compound, and (c) the water-soluble polar solvent as the other component, the resist stripping composition of the present invention may contain 10 to 80% by weight of the compound represented by chemical formula 1, (b) 0.1 to 20% by weight of the alkali compound, and 5 to 80% by weight of the water-soluble polar solvent as the other component, based on the total weight, and more preferably contains 50 to 70% by weight of the compound represented by chemical formula 1, (b) 0.1 to 20% by weight of the alkali compound, and 20 to 40% by weight of the water-soluble polar solvent as the other component (c).
(3) When the resist stripping composition of the present invention contains (a) the compound represented by chemical formula 1, (b) the alkali compound, and (c) water as other components, the resist stripping composition of the present invention may contain 10 to 80 wt% of the compound represented by chemical formula 1, (b) 0.1 to 20 wt% of the alkali compound, and (c) 0.1 to 70 wt% of water as other components, based on the total weight, and more preferably contains 50 to 70 wt% of the compound represented by chemical formula 1, (b) 0.1 to 20 wt% of the alkali compound, and (c) 20 to 40 wt% of water as other components.
(4) When the resist stripping composition of the present invention contains (a) the compound represented by chemical formula 1, (b) the alkali compound, (c) the water-soluble polar solvent and water as the other components, the resist stripping composition of the present invention may contain 10 to 80 wt% of the compound represented by chemical formula 1, (b) 0.1 to 20 wt% of the alkali compound, (c) 5 to 60 wt% of the water-soluble polar solvent and 0.1 to 70 wt% of water as the other components, based on the total weight, and more preferably contains 10 to 60 wt% of the compound represented by chemical formula 1, (b) 0.1 to 20 wt% of the alkali compound, 15 to 50 wt% of the water-soluble polar solvent and 20 to 40 wt% of water as the other components.
In the four forms of the composition, each component may be contained in the more preferable ranges of each component described above.
The resist stripping liquid composition of the present invention can be produced by favorably mixing the above-mentioned compounds in an amount, and the mixing method is not particularly limited, and various known methods can be applied without limitation.
The present invention also provides a method for stripping a resist, which is characterized by using the resist stripping liquid composition of the present invention. The resist stripping method is characterized by comprising:
(I) a step of vapor plating a conductive metal film on a flat display substrate;
(II) forming a resist film on the conductive metal film;
(III) a step of selectively exposing the resist film;
(IV) forming a resist pattern by developing the exposed resist film;
(V) etching the conductive metal film using the resist pattern as a mask; and
(VI) a step of peeling the resist modified and cured by the resist pattern formation and etching from the substrate using the resist remover composition of the present invention after the etching step.
The stripping method of the present invention includes a method of stripping an exposed resist film with the stripping liquid composition of the present invention after a dry etching step or a CMP (chemical mechanical Polishing) step, such as an etch back (etchback) step, is performed without performing a resist pattern forming step using a mask.
In the above-described stripping method, the processes of formation of a resist film, exposure, development, etching, and ashing may be performed by methods generally known in the art.
The types of the above-mentioned resists include positive and negative g-ray, i-ray and Deep Ultraviolet (DUV) resists, electron beam resists, X-ray resists, ion beam resists, and the like, and are not limited by their constituent components, but resists to which the resist stripping composition of the present invention is particularly effectively applied are photoresist films composed of a novolak-based phenolic resin and a diazonaphthoquinone-based photoactive compound, and are also effective for photoresist films composed of a mixture thereof.
As a method for removing a resist, a modified or cured resist, and a dry etching residue on a flat panel display substrate by using the resist stripping liquid composition of the present invention, there can be mentioned a method of immersing a substrate coated with a resist in a stripping liquid, a method of spraying a stripping liquid on the corresponding substrate, and the like. In this case, physical treatment such as irradiation with ultrasonic waves or contact with a brush that rotates or oscillates left and right may be performed in parallel. After the stripping solution treatment, the stripping solution remaining on the substrate can be removed by the subsequent cleaning treatment. The cleaning step is the same as the stripping step except that water or isopropyl alcohol is used instead of the stripping liquid.
Among the above-mentioned peeling methods, a dipping method, a spraying method, or a dipping and spraying method can be used. In the case of peeling by dipping, spraying or dipping and spraying, the temperature is about 15 to 100 ℃, preferably 30 to 70 ℃, and the dipping, spraying or dipping and spraying time is about 30 seconds to 40 minutes, preferably 1 minute to 20 minutes as peeling conditions, but in the present invention, it is not strictly applied and conditions can be modified easily and suitably according to those skilled in the art. If the temperature of the stripper composition applied to the above-described resist-coated substrate is less than 15 deg.c, the time required to remove the modified or cured resist film may become excessively long. Further, if the temperature of the composition exceeds 100 ℃, the lower film layer of the resist film may be damaged, which may cause difficulty in handling the stripping solution.
The resist stripping liquid composition and the stripping method using the same of the present invention can be used not only for removing general resists but also for removing resists and etching residues that are modified or cured by etching gases and high temperatures. The resist stripping liquid composition and the stripping method using the same of the present invention have an advantage of excellent corrosion resistance to metal wiring including aluminum or copper when used for manufacturing a flat panel display.
The present invention also provides a method for producing a flat panel for a display device, comprising a step of stripping a resist of a substrate for a flat panel using the resist stripping liquid composition of the present invention.
The present invention also provides a method for manufacturing a flat panel display device, comprising a step of stripping a resist of a flat panel substrate using the resist stripping liquid composition of the present invention.
The flat panel for display devices and the flat panel display device manufactured by the above manufacturing method have excellent quality because the resist is completely removed in the manufacturing process and corrosion of metal wiring including aluminum and/or copper hardly occurs.
The present invention also provides a method for producing a flat panel for a display device, comprising a step of stripping a resist of a flat panel substrate using the resist stripping liquid composition.
The resist stripping step is the same as described above.
The present invention also provides a flat panel for a display device, which is manufactured by the method for manufacturing a flat panel for a display device.
In addition, the invention provides a flat panel display device, which is characterized by comprising the flat panel.
The present invention will be described in more detail below with reference to examples and comparative examples. However, the following examples and comparative examples are only intended to illustrate the present invention, and the present invention is not limited to the following examples and comparative examples, and various modifications and changes can be made.
Examples 1 to 14 and comparative examples 1 to 4 production of resist stripping liquid compositions
Resist stripping liquid compositions were prepared by mixing the components in the amounts shown in table 1 below.
[ Table 1] (Unit:%)
Figure BDA0001134991420000101
BEEM: bis (2-ethoxyethoxy) methane
BMEM: bis (2-methoxyethoxy) methane
BBEM: bis (2-butoxyethoxy) methane
TDME: triethylene glycol dimethyl ether
The MEDG: diethylene glycol methyl ethyl ether
DGA: diglycolamine
MEA: monoethanolamine
HEP: hydroxy ethyl piperazine
TMAH: tetramethyl ammonium hydroxide
NMP: n-methyl pyrrolidone
THFA: tetrahydrofurfuryl alcohol
EDG (electro-deposition) of: diethylene glycol monoethyl ether
Test example 1 evaluation of peeling force of peeling liquid
In order to confirm the stripping effect of the resist stripping composition, according to a common method, a Mo/Al or Cu/Ti layer was formed on a glass substrate by a thin film sputtering method, and then a photoresist pattern was formed, and then substrates in which metal films were etched were prepared by wet etching and dry etching, respectively. After the temperature of the resist stripping composition was kept constant at 50 ℃, the object was immersed for 10 minutes to evaluate the stripping force. Thereafter, the substrate was cleaned with pure water for 1 minute to remove the residual stripping solution on the substrate, and the substrate was completely dried with nitrogen gas to remove the residual pure water on the substrate after cleaning.
The substrate modification or cured resist and dry etching residue removal performance was confirmed by a scanning electron microscope (SEM, Hitachi S-4700), and the results are shown in table 2 below.
< evaluation criteria >
Very good is represented by ∈ good, good is represented by ≈ good, ordinary is represented by Δ, and failure is represented by ×.
Test example 2 evaluation of resist dissolving ability (evaluation of number of processed sheets/processing Capacity)
5 parts by weight of a solidified resist (DWG-520, Toyobo Fine chemical) (a resist solidified by heat treatment at 130 ℃ for 3 days to remove the whole solvent) was added to 100 parts by weight of the stripping solution, and dissolved at 50 ℃ for 1 hour at 500 rpm. Then, the remaining amount of the resist which was not dissolved was filtered with filter paper and the weight was measured, and then the solubility of the resist was determined. The higher the value, the higher the resist dissolution force, and the number of sheets processed/processing capacity can be determined to be high. The results are shown in table 2 below.
Test example 3 evaluation of volatilization amount in Process of stripping solution
In order to evaluate the amount of the resist stripping solution lost by volatilization in the process, 500g of each of the solutions was added to a 1000ml beaker, the beaker was placed in a thermostatic bath at 50 ℃ to maintain a constant temperature, and the remaining amount in the beaker after 24 hours was measured to calculate the volatilization amount lost by volatilization as%. The results are shown in table 2 below.
[ Table 2]
Figure BDA0001134991420000121
As is clear from table 2 above, in the case of comparative examples 2 to 4 which did not contain the compound represented by chemical formula 1, the volatilization amounts lost by volatilization after 24 hours were 54.6%, 39.4%, and 72.1%, while the volatilization amounts of the resist stripping liquid compositions of examples 1 to 14 were significantly low. In addition, in the case of examples 1 to 14 containing the compound represented by chemical formula 1, when the influence of the alkali-based compound is excluded, high dissolving power is observed, while comparative examples 1 to 4 not containing the compound represented by chemical formula 1 show low dissolving power.

Claims (8)

1. A resist stripping liquid composition, which comprises (a) a compound represented by the following chemical formula 1 and (b) an alkali compound, and optionally further comprises (c) other components except the component (a) and the component (b),
[ chemical formula 1]
Figure FDA0002510768490000011
In the chemical formula 1, n is an integer of 1-3;
R1and R2Each independently hydrogen, C1-C10 alkyl, or a group containing 1-5 oxygen atoms and 2-10 carbon atoms, wherein the oxygen atoms and the carbon atoms form an ether bond;
R3and R4Is absent or each independently C1-C5 alkoxy group; aryl of C6-C12; aryloxy of C6 to C12 substituted or unsubstituted with amino or alkyl of C1 to C5; a hydroxyl group; -CN; or an amino group.
2. The resist stripping liquid composition according to claim 1, characterized by comprising (a) 10 to 99.9 wt% of the compound represented by chemical formula 1, (b) 0.1 to 20 wt% of a base compound, and (c) 0 to 70 wt% of other components, based on the total weight of the composition.
3. The resist stripping solution composition according to claim 1, wherein the compound represented by formula (a) 1 is selected from the group consisting of bis (2-ethoxyethoxy) methane, bis (2-methoxyethoxy) methane, bis (2-butoxyethoxy) methane, 1, 13-diethoxy-3, 6,8, 11-tetraoxa-tridecane, 1, 13-dimethoxy-3, 6,8, 11-tetraoxa-tridecane, formaldehyde [ bis- (2-phenoxyethyl) acetal ], 4- (2- ((2-ethoxyethoxy) methoxy) ethoxy) aniline, formaldehyde [ bis (2-o-tolyloxyethyl) acetal ], 2,4,7,9,12, 14-hexaoxapentadecane, 3,6,9,12,15,18,21, 24-octaoxapentacanol, formaldehyde [ bis (2-isopropoxyethyl) acetal ], 4 '- (2, 2' -methylenebis (oxy) bis (ethane-2, 1-diyl) bis (oxy)) diphenylamine, 4,7,9,12,14, 17-hexaoxaeicosane-1, 20-dinitrile, 1-phenyl-2, 5,7, 10-tetraoxaundecane, and 3,6,8, 11-tetraoxatridecane-1, 13-diamine.
4. The resist stripping solution composition according to claim 1, wherein the alkali compound (b) is one or more selected from the group consisting of KOH, NaOH, tetramethylammonium hydroxide, tetraethylammonium hydroxide, carbonate, phosphate, ammonia, and amines.
5. The resist stripping liquid composition according to claim 1, characterized in that it further comprises one or more selected from water-soluble polar solvents and water as the (c) other component.
6. The resist stripping liquid composition according to claim 5, characterized by comprising (a) 10-98 wt% of the compound represented by chemical formula 1, (b) 0.1-20 wt% of a base compound, and the balance being (c) one or more selected from water-soluble polar solvents and water as other components, based on the total weight of the composition.
7. The resist stripping liquid composition according to claim 5, characterized in that the water-soluble polar solvent uses a protic polar solvent and an aprotic polar solvent, alone or in combination, other than a polyol.
8. A method for producing a flat panel for a display device, comprising a step of stripping a resist from a flat panel substrate using the resist stripping liquid composition according to claim 1.
CN201610916985.1A 2016-03-28 2016-10-20 Resist stripping liquid composition, flat plate, method for manufacturing flat plate, and display device Active CN107239006B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020160036818A KR20170111411A (en) 2016-03-28 2016-03-28 Resist stripper composition, and method for manufacturing a plat panel for a display device and plat panel for a display device, and display device
KR10-2016-0036818 2016-03-28

Publications (2)

Publication Number Publication Date
CN107239006A CN107239006A (en) 2017-10-10
CN107239006B true CN107239006B (en) 2020-09-01

Family

ID=59983425

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201610916985.1A Active CN107239006B (en) 2016-03-28 2016-10-20 Resist stripping liquid composition, flat plate, method for manufacturing flat plate, and display device

Country Status (2)

Country Link
KR (2) KR20170111411A (en)
CN (1) CN107239006B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7057653B2 (en) * 2017-12-08 2022-04-20 花王株式会社 Detergent composition for removing resin mask
CN117460996A (en) * 2021-04-30 2024-01-26 弗萨姆材料美国有限责任公司 Compositions for removing photoresist from substrates and uses thereof

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0629671B1 (en) * 1993-06-15 2002-03-27 Mitsubishi Rayon Co., Ltd. Solvent composition
KR20030032358A (en) * 2001-10-17 2003-04-26 주식회사 엘지화학 Photoresist stripper composition
CN1469918A (en) * 2000-10-16 2004-01-21 ���ֿ����ر��˹�˾ Stable alkaline composition for cleaning microelectronic substrates
WO2004055592A2 (en) * 2002-12-12 2004-07-01 Arch Specialty Chemicals, Inc. Stable non-photosensitive polyimide precursor compoistions for use in bilayer imaging systems
CN1580221A (en) * 2003-08-06 2005-02-16 马林克罗特贝克公司 Stripping and cleaning compositions for microelectronics
KR100733650B1 (en) * 1999-12-28 2007-06-28 미츠비시 가스 가가쿠 가부시키가이샤 Edge Bead Remover
CN101093364A (en) * 2006-06-23 2007-12-26 东京应化工业株式会社 Stripping liquid for photo-induced resist and base plate processing method using the same
CN101952777A (en) * 2007-12-18 2011-01-19 旭化成电子材料株式会社 Method for producing cured resist using negative photosensitive resin laminate, negative photosensitive resin laminate, and method of using negative photosensitive resin laminate
KR101130353B1 (en) * 2011-08-12 2012-03-27 진정복 Stripper composition for photoresist and method for stripping photoresist using the same
CN103064263A (en) * 2011-08-22 2013-04-24 东友Fine-Chem股份有限公司 Resist stripper composition and method of stripping resist using same
CN103336412A (en) * 2013-07-03 2013-10-02 北京科华微电子材料有限公司 A new type of photoresist stripping solution and its application process
CN103713476A (en) * 2012-10-08 2014-04-09 气体产品与化学公司 Stripping and cleaning compositions for removal of thick film resist

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI417274B (en) * 2008-12-04 2013-12-01 Shinetsu Chemical Co Sulfonium salt, acid generator, resist composition, photomask blank, and patterning process
JP5216032B2 (en) * 2010-02-02 2013-06-19 信越化学工業株式会社 Novel sulfonium salt, polymer compound, method for producing polymer compound, resist material and pattern forming method
KR101292163B1 (en) 2010-11-23 2013-08-12 한양대학교 산학협력단 An Anti―Cancer Composition Containing an Antibody of KRT19
FR2976290B1 (en) * 2011-06-09 2014-08-15 Jerome Daviot COMPOSITION OF SOLUTIONS AND CONDITIONS OF USE FOR THE COMPLETE REMOVAL AND DISSOLUTION OF PHOTO-LITHOGRAPHIC RESINS
KR20150000183A (en) * 2013-06-24 2015-01-02 동우 화인켐 주식회사 A resist stripper composition for preparing a flat panel display

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0629671B1 (en) * 1993-06-15 2002-03-27 Mitsubishi Rayon Co., Ltd. Solvent composition
KR100733650B1 (en) * 1999-12-28 2007-06-28 미츠비시 가스 가가쿠 가부시키가이샤 Edge Bead Remover
CN1469918A (en) * 2000-10-16 2004-01-21 ���ֿ����ر��˹�˾ Stable alkaline composition for cleaning microelectronic substrates
KR20030032358A (en) * 2001-10-17 2003-04-26 주식회사 엘지화학 Photoresist stripper composition
WO2004055592A2 (en) * 2002-12-12 2004-07-01 Arch Specialty Chemicals, Inc. Stable non-photosensitive polyimide precursor compoistions for use in bilayer imaging systems
CN1580221A (en) * 2003-08-06 2005-02-16 马林克罗特贝克公司 Stripping and cleaning compositions for microelectronics
CN101093364A (en) * 2006-06-23 2007-12-26 东京应化工业株式会社 Stripping liquid for photo-induced resist and base plate processing method using the same
CN101952777A (en) * 2007-12-18 2011-01-19 旭化成电子材料株式会社 Method for producing cured resist using negative photosensitive resin laminate, negative photosensitive resin laminate, and method of using negative photosensitive resin laminate
KR101130353B1 (en) * 2011-08-12 2012-03-27 진정복 Stripper composition for photoresist and method for stripping photoresist using the same
CN103064263A (en) * 2011-08-22 2013-04-24 东友Fine-Chem股份有限公司 Resist stripper composition and method of stripping resist using same
CN103713476A (en) * 2012-10-08 2014-04-09 气体产品与化学公司 Stripping and cleaning compositions for removal of thick film resist
CN103336412A (en) * 2013-07-03 2013-10-02 北京科华微电子材料有限公司 A new type of photoresist stripping solution and its application process

Also Published As

Publication number Publication date
CN107239006A (en) 2017-10-10
KR20230038158A (en) 2023-03-17
KR102757703B1 (en) 2025-01-21
KR20170111411A (en) 2017-10-12

Similar Documents

Publication Publication Date Title
JP5647685B2 (en) Resist stripping composition and resist stripping method using the same
KR101734593B1 (en) Resist stripper composition and a method of stripping resist using the same
CN110597024B (en) Stain-preventing photoresist stripper composition and method for manufacturing flat panel display substrate
IL183648A (en) Non-aqueous, non-corrosive microelectronic cleaning compositions
KR102757703B1 (en) Resist stripper composition, and method for manufacturing a plat panel for a display device and plat panel for a display device, and display device
KR20130049577A (en) Photoresist stripper composition
EP1877870B1 (en) Non-aqueous photoresist stripper that inhibits galvanic corrosion
KR20090121650A (en) Resist stripper composition and method of peeling resist using same
KR100440484B1 (en) Photoresist stripper composition
JP2004533010A (en) Resist remover composition
CN1682155B (en) Photoresist stripper composition
KR20150000183A (en) A resist stripper composition for preparing a flat panel display
KR20010113396A (en) Photoresist remover composition comprising ammonium fluoride
KR101880302B1 (en) Resist stripper composition and method of stripping resist using the same
KR20170099525A (en) Resist stripper composition
KR101543827B1 (en) Resist stripper composition and a method of stripping resist using the same
KR100568558B1 (en) Photoresist Stripper Composition for Copper Wiring
KR102092919B1 (en) Resist stripper composition and a method of stripping resist using the same
KR102572751B1 (en) Resist stripper composition and method of stripping resist using the same
KR102092336B1 (en) Photoresist stripper composition
KR20140119286A (en) Photoresist stripper composition and method of stripping photoresist using the same
KR102092922B1 (en) Resist stripper composition and a method of stripping resist using the same
KR102091542B1 (en) Resist stripper composition
KR102009532B1 (en) A resist stripper composition
KR20150096244A (en) Resist stripper composition and a method of stripping resist using the same

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant