CN1484095A - Positive photoresist composition and method for forming slushing pattern - Google Patents
Positive photoresist composition and method for forming slushing pattern Download PDFInfo
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- CN1484095A CN1484095A CNA031543014A CN03154301A CN1484095A CN 1484095 A CN1484095 A CN 1484095A CN A031543014 A CNA031543014 A CN A031543014A CN 03154301 A CN03154301 A CN 03154301A CN 1484095 A CN1484095 A CN 1484095A
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
- G03F7/0226—Quinonediazides characterised by the non-macromolecular additives
-
- 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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
-
- 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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
- G03F7/0236—Condensation products of carbonyl compounds and phenolic compounds, e.g. novolak resins
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- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
Abstract
Provided is a resist material with excellent linearity capable of forming a fine resist pattern less than 2.0 [mu]m in a low NA condition with NA less than 0.2, suitably used for system LCD manufacturing.This positive photoresist composition contains (A)alkali-soluble resin, (B) naphthoquinone diazide esterificated substance, (C) at least one kind of phenolic hydroxy group-containing compound selected from a group consisting of compounds expressed by a general formula (I), (R1-R6 are each independently hydrogen atom, halogen atom, 1-6C alkyl group or 1-6C alkoxy group; R7 is hydrogen atom or 1-6C alkyl group; a and b are independently integers 1-3), and (D) an organic solvent.
Description
Technical field
The present invention relates to a kind of positive light anti-etching agent composition of the manufacturing that is used in the LCD that is formed with integrated circuit and liquid-crystal display section on 1 substrate and the formation method of corrosion-resisting pattern.
Background technology
In the manufacturing of semiconductor element, what often use is that composition uses novolac resin and employing contains the repeatedly positive light anti-etching material that system constituted of nitrilo compound of quinone two as the photonasty composition by forming as tunicle.Should be by novolac resin-the contain quinone two positive light anti-etching material that constitutes of nitrilo compound system repeatedly, its less expensive, and can form sensitivity, resolving power, reach the good corrosion-resisting pattern of shape, therefore also be used in the manufacturing of the LCD (liquid crystal display cells) that is formed with liquid-crystal display section on the glass substrate.
But, in the preparation field of LCD, the material, shape of the substrate of coating erosion resistant and even big or smallly also be different from employed substrate in the manufacturing of semiconductor element greatly.
For example, as the substrate of semiconductor element, use be that maximum gauge is the collar plate shape silicon wafer of 8 inches (about 200mm)-12 inches (about 300mm).Relative therewith, as the substrate of LCD, employed is that minimum reaches the square glass substrate about 360mm * 460mm.
Therefore, the erosion resistant for LCD makes usefulness requires it can form shape and the good corrosion-resisting pattern of dimensional stability on the whole base plate face.In addition, in the manufacturing of liquid crystal display cells,, therefore wish the cheap of erosion resistant owing to need a large amount of erosion resistants.
On the other hand, as LCD of future generation, just intimately carry out at present be for the technological development that integrated circuit such as display part, driver, DAC (digital to analog converter), image processor, Video Controller, RAM partly is formed on the high function LCD that is called as " system LCD " on 1 substrate (Semiconductor FPD World 2001.9, pp.50-67).
In the LCD of this system, the size that is formed on the corrosion-resisting pattern on the substrate for example is that with respect to the display part about the 2-10 micron, integrated circuit partly is about the 0.5-2.0 micron, and is finer.
If will form this pattern dimension display part inequality and integrated circuit part simultaneously, require to provide the linear excellent erosion resistant under the same conditions of exposure.Linearity is meant the characteristic of reproducing the mask size with same conditions of exposure (the mask size difference on the graticule (reticule) but the identical condition of exposure) when exposing on graticule.
In addition, if want the trickle pattern of integrated circuit part, then need to adopt the erosion resistant that has higher resolution more in the past than the liquid crystal display cells manufacturing that was used to form the bigger display part of pattern dimension with erosion resistant.
Resolution (resolving limit) can be with the Rayleigh formula R=k that is expressed from the next
1(in the formula, R represents resolving limit to * λ/NA, k
1The proportionality constant of resist, operation, image forming method is depended in expression, and λ represents to be used for the light wavelength of exposure process, and NA represents the numerical aperture of lens) expression.
Therefore, if improve resolution R, need (1) to use the short light source of wavelength X, (2) adopt the exposure process of high NA.
Under the situation of (1), one of effective ways are for example to use employed g line (436nm) exposure when the fine corrosion-resisting pattern that forms below 2.0 microns is replaced by the photoetching technique that adopts shorter i line (365nm) exposure of wavelength.
On the other hand, under the situation of (2),, can finish enforcement by use the lens of high NA as far as possible.
Yet, in the manufacturing field of LCD, consider from improving handling capacity (the processing quantity in the unit interval) angle, need expand the exposure area to 100mm at least
2About.If but the NA of raising lens, the depth of focus will shoal, so the big more inner evenness that is not easy to keep exposed portion more of exposure area.
Therefore, in LCD manufacturing field, realize some difficulty of high NAization, it has been generally acknowledged that employing for example the exposure process of the low NA condition below 0.2 be advisable.
But the linearity of erosion resistant under low NA condition of LCD manufacturing usefulness in the past is not good, is difficult to the fine anti-pattern about the 0.5-2.0 micron is formed good shape.In addition, adopting in the past LCD to make the cross sectional shape of the resulting corrosion-resisting pattern of erosion resistant of usefulness neither rectangle, has tapered tendency.
For example, about the erosion resistant of in the past liquid crystal display cells manufacturing usefulness, be disclosed in the spy in a large number and open flat 9-160231 communique, spy and open flat 9-211855 communique, spy and open 2000-112120 communique, spy and open that 2000-131835 communique, spy are opened the 2000-181055 communique, the spy opens on the communiques such as 2001-75272 communique.
Be recorded in the material on the above-mentioned communique, it is cheap, and when forming larger-size pattern, its coating, sensitivity, and resolution good, can form the good corrosion-resisting pattern of shape and dimensional stability.Therefore, when being purpose to make the LCD that only has display part (not having the integrated circuit part), these materials are more suitable.
But,, then need to improve its linearity under low NA condition if will in the operation of making above-mentioned system LCD, use.
Summary of the invention
That is, the object of the present invention is to provide and improved linear erosion resistant, so that it also can form the fine corrosion-resisting pattern below 2.0 microns under NA for example is the low NA condition that is suitable for manufacturing system LCD below 0.2.
In order to address the above problem, through studying intensively, the positive light anti-etching agent composition that discoveries such as the inventor contain specific triphen base class sensitizer (compound that contains the phenol hydroxyl) has favorable linearity under low NA condition, be the erosion resistant that is suitable as the manufacturing usefulness of the system LCD that on 1 substrate, is formed with integrated circuit and liquid-crystal display section, to such an extent as to finish the present invention.
Promptly, positive light anti-etching agent composition of the present invention is the LCD manufacturing positive light anti-etching agent composition that is formed with integrated circuit part and liquid-crystal display section on 1 substrate, it is characterized in that, contain from containing the phenol hydroxyl compound by at least a kind that selects (A) alkali soluble resins, (B) naphthoquinones two group that repeatedly nitrogen carboxylate, (C) use the compound of note general formula (I) expression down to form; Reach (D) organic solvent,
[changing 8]
[in the formula, R
1-R
6Independent respectively expression hydrogen atom, halogen atom, the alkyl of carbon number 1-6 or the alkoxy of carbon number 1-6, R7 represents the alkyl of hydrogen atom or carbon number 1-6, the integer of the independent respectively expression 1-3 of a and b].
And then the formation method of corrosion-resisting pattern of the present invention is characterised in that, comprising: (1) is coated on described positive light anti-etching agent composition on the substrate, forms the operation of filming; (2) carry out heat treated to being formed with described substrate of filming, on substrate, form the operation of tunicle against corrosion; (3 usefulness are painted with corrosion-resisting pattern below 2.0 microns simultaneously and form with mask pattern with greater than 2.0 microns corrosion-resisting pattern and form mask with mask pattern, the operation of described tunicle against corrosion being carried out the selectivity exposure; (4) implement the development treatment of employing aqueous alkali for the tunicle against corrosion after the exposure of described selectivity, in the operation of the corrosion-resisting pattern that to form pattern dimension on the described substrate simultaneously be the corrosion-resisting pattern used of the integrated circuit below 2.0 microns and size uses greater than 2.0 microns liquid-crystal display section; (5) wash the flushing operation that remains in the lip-deep developer solution of described corrosion-resisting pattern off.
Description of drawings
Fig. 1 is the key diagram that developer solution is applied to the operation of Z from substrate end X.
Embodiment
In the present invention, as mentioned above, system LCD is meant the LCD that is formed with integrated circuit and liquid-crystal display section on 1 substrate.
In positive light anti-etching agent composition of the present invention, (A) composition there is not special restriction, tunicle that can be from be often used as positive light anti-etching agent composition forms in the material of material and selects arbitrarily to use.
As this alkali soluble resins, for example can enumerate, with aldehydes such as phenols such as phenol, metacresol, paracresol, xylenols, pseudocuminol and formaldehyde, formaldehyde presoma, 2-hydroxy benzaldehyde, 3-hydroxy benzaldehyde, 4-hydroxy benzaldehyde, the novolac resin that under the acidic catalyst condition, obtains through condensation; The hydroxy styrenes resinoids such as multipolymer of the multipolymer of the homopolymer of hydroxy styrenes or hydroxy styrenes and other styrene monomer, hydroxy styrenes and acrylic or methacrylic acid or derivatives thereof; As the alkali soluble resinss such as acrylic or methacrylic acid resin of the multipolymer of acrylic or methacrylic acid and its derivant etc.
Particularly, make to contain metacresol and 3, the phenols of 4-xylenols carries out condensation reaction with the aldehydes that contains propionic aldehyde and formaldehyde and the phenolics that obtains is suitable for the modulation of high sensitivity and linear good erosion resistant.
In positive light anti-etching agent composition of the present invention, (B) composition there is not special restriction, can repeatedly select arbitrarily to use the nitrogen ester compounds from the naphthoquinones two of the photographic composition that was used as resist in the past.Particularly, with the represented phenolic compounds of following note general formula (II) and naphthoquinones two repeatedly the carboxylate of nitrogen sulfoacid compound be suitable for photoetching process with the i line, and be suitable for forming for example situation of the fine corrosion-resisting pattern below 2.0 microns with good shape.
[changing 9]
[in the formula, R
1-R
8The alkyl of independent respectively expression hydrogen atom, halogen atom, carbon number 1-6, the alkoxy of carbon number 1-6, or the naphthenic base of carbon number 3-6, R
9-R
11The alkyl of respectively independent expression hydrogen atom, carbon number 1-6, Q represent hydrogen atom, also can with R
9End combine and form carbon number 3-6 naphthenic base carbon number 1-6 alkyl or by remembering the represented residue of chemical formula (III) down, a, b represent the integer of 1-3 respectively independently, d represents the integer of 0-3, n represents the integer of 0-3,
[changing 10]
(in the formula, R
12And R
13The alkyl of representing hydrogen atom, halogen atom, carbon number 1-6 respectively independently, the alkoxy of carbon number 1-6, or the naphthenic base of carbon number 3-6, c represents the integer of 1-3)].
In addition, as Q and R
9, and Q and R
9Between carbon atom when together forming the naphthenic base of carbon number 3-6, Q and R
9Combine into the alkylidene of carbon number 2-5.
As the phenolic compounds that is equivalent to this general formula (II), can enumerate three (4-hydroxy phenyl) methane, two (4-hydroxy-3-methyl phenyl)-2-hydroxy phenyl methane, two (4-hydroxyls-2,3, the 5-trimethylphenyl)-2-hydroxy phenyl methane, two (4-hydroxyls-3, the 5-3,5-dimethylphenyl)-4-hydroxy phenyl methane, two (4-hydroxyls-3, the 5-3,5-dimethylphenyl)-3-hydroxy phenyl methane, two (4-hydroxyls-3, the 5-3,5-dimethylphenyl)-2-hydroxy phenyl methane, two (4-hydroxyls-2, the 5-3,5-dimethylphenyl)-4-hydroxy phenyl methane, two (4-hydroxyls-2, the 5-3,5-dimethylphenyl)-3-hydroxy phenyl methane, two (4-hydroxyls-2, the 5-3,5-dimethylphenyl)-2-hydroxy phenyl methane, two (4-hydroxyls-3, the 5-3,5-dimethylphenyl)-3,4-dihydroxy benzenes methylmethane, two (4-hydroxyls-2, the 5-3,5-dimethylphenyl)-3,4-dihydroxy benzenes methylmethane, two (4-hydroxyls-2, the 5-3,5-dimethylphenyl)-2,4-dihydroxy benzenes methylmethane, two (4-hydroxy phenyl)-3-methoxyls-4-hydroxy phenyl methane, two (5-cyclohexyl-4-hydroxy-2-methyl phenyl)-4-hydroxy phenyl methane, two (5-cyclohexyl-4-hydroxy-2-methyl phenyl)-3-hydroxy phenyl methane, two (5-cyclohexyl-4-hydroxy-2-methyl phenyl)-2-hydroxy phenyl methane, two (5-cyclohexyl-4-hydroxy-2-methyl phenyl)-3, triphenol type compounds such as 4-dihydroxy benzenes methylmethane;
2, two (3,5-dimethyl-4-the hydroxybenzyl)-5-hydroxyl phenols, 2 of 4-, two (2,5-dimethyl-4-the hydroxybenzyl)-line style 3 ring body phenolic compounds such as 4-methylphenol of 6-;
1, two [3-(2-hydroxy-5-methyl base benzyl)-4-hydroxyl-5-cyclohexyl phenyl] the different propane of 1-, two [2,5-dimethyl-3-(4-hydroxy-5-methyl base benzyl)-4-hydroxy phenyl] methane, two [2,5-dimethyl-3-(4-hydroxybenzyl)-4-hydroxy phenyl] methane, it is two that [3-(3,5-dimethyl-4-hydroxybenzyl)-and 4-hydroxy-5-methyl base phenyl] methane, it is two that [3-(3,5-dimethyl-4-hydroxybenzyl)-and 4-hydroxyl-5-ethylphenyl] methane, it is two that [3-(3,5-diethyl-4-hydroxybenzyl)-and 4-hydroxy-5-methyl base phenyl] methane, it is two that [3-(3,5-diethyl-4-hydroxybenzyl)-and 4-hydroxyl-5-ethylphenyl] methane, two [2-hydroxyl-3-(3,5-dimethyl-4-hydroxybenzyl)-and the 5-aminomethyl phenyl] methane, two [2-hydroxyl-3-(2-hydroxy-5-methyl base benzyl)-5-aminomethyl phenyl] methane, two [4-hydroxyl-3-(2-hydroxy-5-methyl base benzyl)-5-aminomethyl phenyl] methane, line style 4 ring body phenolic compounds such as two [2,5-dimethyl-3-(2-hydroxy-5-methyl base benzyl)-4-hydroxy phenyl] methane;
2, two [2-hydroxyl-3-(4-hydroxybenzyl)-5-the methyl-benzyl]-6-cyclohexylphenol, 2 of 4-, two [4-hydroxyl-3-(4-hydroxybenzyl)-5-the methyl-benzyl]-6-cyclohexylphenol, 2 of 4-, two [2,5-dimethyl-3-(2-hydroxy-5-methyl base benzyl)-4-the hydroxybenzyl]-line style polyphenolic substances such as line styles such as 4-methylphenol 5 ring body phenolic compounds of 6-;
Two (2,3,4-trihydroxy phenyl) methane, two (2, the 4-dihydroxy phenyl) methane, 2,3,4-trihydroxy phenyl-4 '-hydroxy phenyl methane, 2-(2,3,4-trihydroxy phenyl)-2-(2 ', 3 ', 4 '-trihydroxy phenyl) propane, 2-(2, the 4-dihydroxy phenyl)-2-(2 ', 4 '-dihydroxy phenyl) propane, 2-(4-hydroxy phenyl)-2-(4 '-hydroxy phenyl) propane, 2-(3-fluoro-4-hydroxy phenyl)-2-(3 '-fluoro-4 '-hydroxy phenyl) propane, 2-(2, the 4-dihydroxy phenyl)-2-(4 '-hydroxy phenyl) propane, 2-(2,3,4-trihydroxy phenyl)-2-(4 '-hydroxy phenyl) propane, 2-(2,3,4-trihydroxy phenyl)-bisphenol type compounds such as 2-(4 '-hydroxyl-3 ', 5 '-3,5-dimethylphenyl) propane;
1-[1-(4-hydroxy phenyl) isopropyl]-4-[1, two (4-hydroxy phenyl) ethyls of 1-] benzene, 1-[1-(3-methyl-4-hydroxy phenyl) isopropyl]-4-[1, two (3-methyl-4-hydroxy phenyl) ethyls of 1-] many ring branched chain type compounds such as benzene;
1, condensed type phenolic compounds such as 1-bis(4-hydroxyphenyl)cyclohexane etc.
Wherein, contain two (2-methyl-4-hydroxyl-5-cyclohexyl phenyl)-3,4-dihydroxy benzenes methylmethane, two (2, the 4-dihydroxy phenyl) methane, and two (2,3,5-trimethyl-4-hydroxy phenyl)-and the naphthoquinones of 3 kinds of phenolic compounds such as the 2-hydroxy phenyl methane two photoresist immunomodulator compounds of nitrogen ester compounds repeatedly, the shape of its sensitivity, resolving power, corrosion-resisting pattern is good, and is therefore preferred.
To implement repeatedly nitrogen sulfonic acid esterification method of naphthoquinones two by all or part of phenol hydroxyl in the represented compound of above-mentioned general formula (II), can carry out according to method commonly used.For example, make naphthoquinones two repeatedly the nitrogen sulfonic acid chloride carry out condensation with compound by above-mentioned general formula (II) expression.Be specially,-quantitative compound and naphthoquinones-1 by above-mentioned general formula (II) expression, 2-two is nitrogen base-4-sulfonic acid chloride or naphthoquinones-1 repeatedly, 2-two repeatedly nitrogen base-5-sulfonic acid chloride is dissolved in the organic solvents such as dioxane, n-methyl pyrrolidone, dimethyl acetamide, tetrahydrofuran, wherein add base catalysts such as triethylamine, triethanolamine, pyridine, carbonic acid alkali metal salt, bicarbonate alkali metal salt again and react, and washing, dry products therefrom.
As (B) composition, except above-mentioned naphthoquinones two repeatedly the nitrogen carboxylate, the naphthoquinones two that also can use other is the nitrogen carboxylate repeatedly.For example, also can adopt the repeatedly esterification reaction product etc. of nitrogen sulfoacid compound of phenolic compounds such as poly-dihydroxy benaophenonel or alkyl gallates and naphthoquinones two.The use amount that change the nitrogen carboxylate when this other naphthoquinones two accounts for below the 80 quality % of (B) composition, when particularly 50 quality % are following, can not damage effect of the present invention, and is therefore preferred.
In positive light anti-etching agent composition of the present invention, (B) use level of composition at 10-70 quality %, preferably is chosen as suitable with respect to the total quality of (A) composition and following (C) composition in the mass range of 20-40 quality %.If (B) use level of composition is lower than above-mentioned scope, then can not get being loyal to the image of pattern, its transcribing property might descend.On the other hand, if (B) use level of composition surpasses above-mentioned scope, then might cause the sensitivity deterioration and come from the deterioration of resolving power of the homogeneous decline of formed etchant resist.
Bigger characteristics at positive light anti-etching agent composition of the present invention are, as (C) composition, be combined with at least a kind of selecting and contain the phenol hydroxyl compound from the compound by above-mentioned general formula (I) expression.This by cooperating (C) compound can obtain can forming positive light anti-etching agent composition linear good pattern, that be suitable as the LCD of system manufacturing usefulness under low NA condition.This positive light anti-etching agent composition also is applicable to i line exposing operation, and almost can't see foam after the exposure imaging on substrate.
Phenol hydroxyl compound as by formula (I) expression does not have special restriction, and for example, the triphenol type compound of being represented by following formula (Ia)-(If) can show above-mentioned characteristic, and is therefore preferred.
[changing 11]
Compound by this formula (Ia) expression has good sensitivity, and is therefore preferred.
[changing 12]
Compound by this formula (Ib) expression all can reach good overall equilbrium to sensitivity, linearity, resolving power etc., and is therefore preferred.
[changing 13]
By the compound of this formula (Ic) expression, its linearity is good especially, and is therefore preferred.
[changing 14]
Compound by this formula (Id) expression has good sensitivity and thermotolerance, and is therefore preferred.
[changing 15]
Thermotolerance by the compound of this formula (Ie) expression is relatively good, therefore preferred.
[changing 16]
By the compound of this formula (If) expression, its sensitivity and thermotolerance are very good, and be therefore preferred.
(C) use level of composition, is preferably selected from the scope of 20-40 quality % from 10-70 quality % with respect to the alkali soluble resins as (A) composition.If (C) use level of composition is in above-mentioned scope, then the sensitivity in i line exposing operation etc. is good, can improve linearity.In addition, under NA is low NA condition below 0.2, also can form the fine corrosion-resisting pattern below 2.0 microns.
Composition of the present invention preferably is dissolved in (A)-(C) composition and the various adding ingredients that cooperated as required in following (D) composition as organic solvent, uses with the form of solution.
As (D) composition, have no particular limits, but from coating, and tunicle thickness against corrosion on large-size glass substrate have good uniformity aspect consider, preferably contain the propylene-glycol monoalky lether acetic acid esters or/and lactic acid alkyl ester.
In the propylene-glycol monoalky lether acetic acid esters, preferred especially propylene glycol methyl ether acetate (hereinafter referred to as " PGMEA "), the film thickness uniformity of its tunicle against corrosion on large-size glass substrate is very good.
In addition, in lactic acid alkyl ester, most preferably ethyl lactate when using on the large-size glass substrate more than 500mm * 600mm, owing to use meeting generation crawling even separately, therefore uses with the mixed system with other solvent and is advisable.
Particularly, contain the composition of propylene-glycol monoalky lether acetic acid esters and lactic acid alkyl ester simultaneously, the film thickness uniformity of its tunicle against corrosion is good, can form the good corrosion-resisting pattern of shape, and can improve thermotolerance, and suppress the generation of foam, and is therefore preferred.
When mix using propylene-glycol monoalky lether acetic acid esters and lactic acid alkyl ester, with respect to the propylene-glycol monoalky lether acetic acid esters, cooperate 0.1-10 doubly to measure with mass ratio, be preferably the lactic acid alkyl ester that 1-5 doubly measures and be advisable.
In addition, (D) in the composition, or/and the lactic acid alkyl ester, also can mix other organic solvent such as gamma-butyrolacton or propylene glycol monobutyl ether except the propylene-glycol monoalky lether acetic acid esters.When using gamma-butyrolacton, with respect to the propylene-glycol monoalky lether acetic acid esters, doubly measure at 0.01-1 with mass ratio, cooperate in the scope that preferred 0.05-0.5 doubly measures and be advisable.
Also have,, for example can enumerate ketones such as acetone, butanone, cyclohexanone, methyl isoamyl ketone as other organic solvent except gamma-butyrolacton and propylene glycol monobutyl ether; Polyalcohols and derivants thereof such as ethylene glycol, propylene glycol, diglycol, ethylene glycol acetate, propylene glycol monoacetate, diglycol monotertiary acetic acid esters or their monomethyl ether, single ether, single propyl ether, monobutyl ether or monophenyl ether; Cyclic ethers classes such as dioxane; Reach ester classes such as methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, ethyl pyruvate, methoxypropionic acid methyl esters, epoxy radicals ethyl propionate.
When using these other solvents,, below 50 quality %, be advisable with respect to propylene-glycol monoalky lether acetic acid esters, lactic acid alkyl ester or their potpourri.
In addition, when repeatedly the nitrogen carboxylate uses the photonasty composition of non-benzophenone as (B) naphthoquinones two,, can preferably use 2-heptanone (hereinafter referred to as " HE ") as (D) composition.Compare with PGMEA, HE can obtain the resist composition that thermotolerance is good and the foam generation is less, so it is very desirable solvent.HE can use separately, also can mix use with above-mentioned organic solvent.
In the present invention, in the scope that does not undermine the object of the invention, can use various adjuvants such as surfactant, ultraviolet light absorber, preservation stabilization agent.
As surfactant, can enumerate Off ロ ラ-De FC-430, FC-431 (trade name is Sumitomo 3M society system); ェ Off ト ッ プ EF122A, EF122B, EF122C, EF126 (trade name is ト-ケ system プ ロ ダ Network ッ society system); メ ガ Off ァ ッ Network R-08 fluorochemical surfactants such as (trade name, the chemical society of big Japanese ink systems).As ultraviolet light absorber, can enumerate 2,2 ' 4,4 '-tetrahydroxybenzophenone, 4-dimethylamino-2 ', 4 '-dihydroxy benaophenonel, 5-amino-3-methyl isophthalic acid-phenyl-4-(4-hydroxy phenyl azo group) pyrazoles, 4-dimethylamino-4 '-hydroxyl azo group benzene, 4-diethylin-4 '-ethoxy azobenzene, 4-diethylin azobenzene, curcumin etc.
In addition, also can use be not contained in by in (C) composition of described general formula (I) expression and in photo-corrosion-resisting agent composition, be used as sensitizer usually contain phenol hydroxyl compound, i.e. compound (E).When using this composition (E), the cooperation total amount of (C) composition and (E) composition is become to be divided into 10-70 quality % scope with respect to (A) be advisable, preferably be located in the 20-40 quality % scope.In addition, employed (C) composition and (E) in the total amount of composition, (E) composition is advisable below 50 quality %.As (E) composition, can enumerate phenolic compounds by above-mentioned formula (II) expression.Wherein, 1-[1, two (4-hydroxy phenyl) ethyls of 1-]-4-[1-(4-hydroxy phenyl) isopropyl] the raising sensitivity of benzene is respond well, therefore preferred.
The following describes the system LCD that has used the present composition and make one of desirable formation method with corrosion-resisting pattern example.
At first, with (A) composition, (B) composition and (C) composition and the various compositions that added as required be dissolved in as in the solvent of (D) composition, and it is coated on the substrate with glue spreader etc.As substrate preferred glass substrate.As this glass substrate, can use more than 500mm * 600mm, especially the large substrate more than 550mm * 650mm.
Then,, remove residual solvent, form tunicle against corrosion by for example carrying out heat treated (prebake) at 100-140 ℃ to being formed with this substrate of filming.As the prebake method, preferably carry out between electric hot plate and substrate, keeping the vicinity (proximity) in gap to cure.
Below, adopting and being painted with pattern dimension for example simultaneously is that corrosion-resisting pattern that the integrated circuit that (is preferably the 0.5-2.0 micron) below 2.0 microns is used forms and surpasses corrosion-resisting pattern that the liquid-crystal display section of 2.0 microns (are preferably surpass 2.0 microns and below 10 microns) uses with mask pattern and pattern dimension and form mask with mask pattern, with required light source tunicle against corrosion is carried out selectivity and exposes.
As at this employed light source,, preferably use i line (365nm) in order to form fine pattern.In addition, adopt the exposure process of this exposure to be preferably NA, more preferably the operation under the low NA condition below 0.15 below 0.2.
Afterwards, adopt the aqueous alkalis such as tetramethylammonium hydroxide aqueous solution of developer solution such as 1-10 quality % that the tunicle against corrosion after the selectivity exposure is implemented development treatment.Thus, exposed portion is removed in dissolving, can form the corrosion-resisting pattern that corrosion-resisting pattern that integrated circuit uses and liquid-crystal display section are used on substrate simultaneously.
Then, stay the lip-deep developer solution of corrosion-resisting pattern, can form corrosion-resisting pattern by washing off with washing fluids such as pure water.
[embodiment]
Below, further describe the present invention with embodiment.
Embodiment 1
(A) composition:
Alkali soluble resins (A1) 100 mass parts
A1: with metacresol/3, the mixed phenol of 4-xylenols=9/1 (mol ratio), and as the mixed aldehyde of propionic aldehyde/formaldehyde=1/3 (mol ratio) of condensation agent, according to the synthetic Mw=4750 of method commonly used, the novolac resin of Mw/Mn=2.44
(B) composition:
Naphthoquinones two is nitrogen carboxylate (potpourri of B1/B2/B3=6/1/1 (mass ratio)) 35 mass parts repeatedly
Two (2-methyl-4-hydroxyl-5-cyclohexyl phenyl)-3 of B1:1 mole, 1 of 4-dihydroxy benzenes methylmethane and 2 moles, 2-naphthoquinones two is the esterification reaction product of nitrogen base-5-sulfonic acid chloride (hereinafter referred to as " 5-NQD ") repeatedly
The esterification reaction product of two (2, the 4-dihydroxy phenyl) methane of B2:1 mole and 4 moles 5-NQD
B3: the esterification reaction product of the 5-NQD of two (2,3,5-trimethyl-4-hydroxy phenyl)-2-hydroxy phenyl methane and 2 moles
(C) composition:
Contain phenol hydroxyl compound 25 mass parts by following formula (Ia) expression
[changing 17]
To be equivalent to the surfactant (trade name " R-08 " of 350ppm with respect to above-mentioned (A)-(C) composition, and (A)-(C) the total quality of composition; Big Japanese ink (strain) society system) is dissolved among the PGMEA ((D) composition).The use amount of (D) composition is adjusted to makes solid shape branch [(A)-(C) total of composition] concentration reach the amount of 25-28 quality % concentration.With the aperture is that 0.2 micron membrane filter filters this, has modulated positive light anti-etching agent composition.
Embodiment 2-9, comparative example 1-2
The material of in use level (mass parts) the use table of being put down in writing with table 1 as (A)-(E) composition 1, being put down in writing, modulated positive light anti-etching agent composition in the same manner with embodiment 1.Also have, use amount that will (D) composition is adjusted to and makes solid shape branch [(A)-(C) reaching (E) total of composition] concentration reach the amount of 25-28 quality % concentration.
[table 1]
| (A) (mass parts) | (B) (mass ratio) (mass parts) | (C) (mass parts) | (D) | (E) (mass parts) | |
| Embodiment 1 | ??A1 ??(100) | B1/B2/B3 (6/1/1) (35) | The compound (25) of formula (Ia) | PGMEA | |
| Embodiment 2 | ??A1 ??(100) | B1/B2/B3 (6/1/1) (35) | The compound (25) of formula (Ib) | PGMEA | |
| Embodiment 3 | ??A1 ??(100) | B1/B2/B3 (6/1/1) (35) | The compound (25) of formula (Ic) | PGMEA | |
| Embodiment 4 | ??A1 ??(100) | B1/B2/B3 (6/1/1) (35) | The compound (25) of formula (Id) | PGMEA | |
| Embodiment 5 | ??A1 ??(100) | B1/B2/B3 (6/1/1) (35) | The compound (25) of formula (Ie) | PGMEA | |
| Embodiment 6 | ??A1 ??(100) | B1/B2/B3 (6/1/1) (35) | The compound (25) of formula (If) | PGMEA | |
| Embodiment 7 | ??A1 ??(100) | B1/B2/B3 (6/1/1) (35) | The compound (12.5) of formula (Ib) | PGMEA | ?E1(12.5) |
| Embodiment 8 | ??A1 ??(100) | B1/B2/B3 (6/1/1) (35) | The compound (25) of formula (Ib) | HE | |
| Embodiment 9 | ??A2 ??(100) | B1/B2/B3 (6/1/1) (35) | The compound (25) of formula (Ib) | PGMEA | |
| Embodiment 10 | ??A1 ??(100) | B1/B4 (1/1) (35) | The compound (25) of formula (Ib) | PGMEA | |
| Comparative example 1 | ??A1 ??(100) | B1/B2/B3 (6/1/1) (35) | PGMEA | ?E2(25) | |
| Comparative example 2 | ??A1 ??(100) | B1/B2/B3 (6/1/1) (35) | PGMEA | ?E3(25) |
In table 1, the implication that each symbolic representation is following.
A2: with metacresol/paracresol/2,3, the mixed phenol of 5-pseudocuminol=9/0.5/0.5 (mol ratio), and as the mixed aldehyde of formaldehyde/crotonaldehyde=2/1 (mol ratio) of condensation agent, according to the synthetic Mw=7000 of method commonly used, the novolac resin of Mw/Mn=3.05
The esterification reaction product of the 5-NQD of B4:1 mole gallicin and 3 moles
E1:1-[1, two (4-hydroxy phenyl) ethyls of 1-]-4-[1-(4-hydroxy phenyl) isopropyl] benzene
E2:2,3,4,4 '-tetrahydroxybenzophenone
E3: two [2-hydroxyl-3-(2-hydroxy-5-methyl base benzyl)-5-aminomethyl phenyl] methane PGMEA: propylene glycol methyl ether acetate
The HE:2-heptanone
Test example 1
The positive light anti-etching agent composition that is obtained by embodiment 1-9 and comparative example 1-2 has been carried out following each rerum natura (1)-(3) to be estimated.These evaluation results are shown in Table 2.
(1) linear evaluation:
With glue spreader positive light anti-etching agent composition is coated on the glass substrate that is formed with the Cr film (on the 550mm * 650mm).Afterwards, be set on 130 ℃ the electric hot plate, utilizing the vicinity of about 1mm of being separated by to cure, carrying out the 1st drying in 60 seconds.Then, electric plate temperature is transferred to 120 ℃, utilizes the vicinity of about 0.5mm of being separated by to cure, implemented the 2nd drying in 60 seconds, formed thickness and be 1.5 microns tunicle against corrosion.
Then, be used to form 3.0 microns line and space (L﹠amp by having simultaneously; The mask pattern of corrosion-resisting pattern S) and be used to form 1.5 microns L﹠amp; The test mask of the mask pattern of S corrosion-resisting pattern (graticule) is with i line exposing device (device name: FX-702J, Nikon society system; NA=0.14), carried out the selectivity exposure.Exposure is made as is enough to 3.0 microns L﹠amp of faithful reappearance; The exposure of S (Eop exposure).
Then, with (the device name: TD-39000 sample machine of the developing apparatus with slit coater (slit coater) nozzle, chemical industry (strain) system is answered in Tokyo), be that Tetramethylammonium hydroxide (TMAH) aqueous solution of 2.38 quality % is coated on the substrate with 23 ℃, concentration.At this moment, as shown in Figure 1, begin through Y until the other end Z, be coated on the substrate with 10 seconds times from a side end X of substrate.Keep after 55 seconds, washed 30 seconds, and Rotary drying.
Afterwards, observation post gets the cross sectional shape of corrosion-resisting pattern with SEM (scanning electron microscope) photo, and has estimated 1.5 microns L﹠amp; The repeatability of the corrosion-resisting pattern of S.
(2) sensitivity evaluation:
Index as estimating sensitivity has adopted above-mentioned Epo exposure.
(3) resolving power evaluation:
Obtained the limiting resolution under the above-mentioned Epo exposure.
In the eurymeric resist composition of comparative example 1,2, owing to fail to draw 1.5 microns L﹠amp; Therefore the S pattern fails to carry out linear evaluation.
Relative therewith, positive light anti-etching agent composition of the present invention has all demonstrated favorable linearity.And then sensitivity, resolving power are well, have all reached good balance between all assessment items that comprise linearity.
Table 2
| Embodiment | Linear evaluation (micron) | Sensitivity is estimated (mJ) | Resolving power is estimated (micron) |
| ?1 | ?1.55 | ?60 | ?1.3 |
| ?2 | ?1.52 | ?50 | ?1.3 |
| ?3 | ?1.50 | ?85 | ?1.3 |
| ?4 | ?1.55 | ?65 | ?1.3 |
| ?5 | ?1.55 | ?80 | ?1.3 |
| ?6 | ?1.58 | ?42.5 | ?1.4 |
| ?7 | ?1.51 | ?47.5 | ?1.3 |
| ?8 | ?1.55 | ?70 | ?1.3 |
| ?9 | ?1.70 | ?50 | ?1.4 |
| ?10 | ?1.55 | ?70 | ?1.4 |
| Comparative example 1 | ?- | More than 100 | ?- |
| ?2 | ?- | More than 100 | ?- |
As described above, the linearity of positive light anti-etching agent composition of the present invention under low NA condition is good.Therefore, can on 1 substrate, form coarse pattern and fine pattern, thereby can be used as the positive light anti-etching agent composition that is manufactured on LCD (system LCD) usefulness that is formed with integrated circuit and liquid-crystal display section on 1 substrate with same conditions of exposure.
In addition, according to the formation method of the corrosion-resisting pattern of the present invention that adopts the linear good described positive light anti-etching agent composition under the low NA condition, can form the fine corrosion-resisting pattern of the manufacturing that is applicable to the LCD of system.
Claims (13)
1. positive light anti-etching agent composition, be to be used to be manufactured on the positive light anti-etching agent composition that is formed with the LCD of integrated circuit and liquid-crystal display section on 1 substrate, it is characterized in that, contain from containing the phenol hydroxyl compound by at least a kind that selects (A) alkali soluble resins, (B) naphthoquinones two group that repeatedly nitrogen carboxylate, (C) are made up of the compound of remembering general formula (I) expression down; Reach (D) organic solvent,
[changing 1]
In the formula, R
1-R
6The alkyl of respectively independent expression hydrogen atom, halogen atom, carbon number 1-6 or
The alkoxy of carbon number 1-6, R7 are represented the alkyl of hydrogen atom or carbon number 1-6, and a and b are respectively
The integer of independent expression 1-3.
2. positive light anti-etching agent composition according to claim 1 is characterized in that, described (C) composition is by formula (Ia):
The compound of expression.
3. positive light anti-etching agent composition according to claim 1 is characterized in that, described (C) composition is by formula (Ib):
The compound of expression.
4. positive light anti-etching agent composition according to claim 1 is characterized in that, described (C) composition is by formula (Ic):
The compound of expression.
5. positive light anti-etching agent composition according to claim 1 is characterized in that, described (C) composition is by formula (Id):
The compound of expression.
6. positive light anti-etching agent composition according to claim 1 is characterized in that, described (C) composition is by formula (Ie):
The compound of expression.
7. positive light anti-etching agent composition according to claim 1 is characterized in that, described (C) composition is by formula (If):
The compound of expression.
8. positive light anti-etching agent composition according to claim 1 is characterized in that, contains the propylene-glycol monoalky lether acetic acid esters in described (D) composition.
9. positive light anti-etching agent composition according to claim 1 is that i line exposing operation is used.
10. positive light anti-etching agent composition according to claim 1 is that NA is at the exposure process-use below 0.2.
11. the formation method of a corrosion-resisting pattern is characterized in that, comprising: (1) is coated on each described positive light anti-etching agent composition among the claim 1-10 on the substrate, forms the operation of filming; (2) carry out heat treated to being formed with described substrate of filming, on substrate, form the operation of tunicle against corrosion; (3) form with mask pattern with greater than 2.0 microns corrosion-resisting pattern and form mask with mask pattern, the operation of described tunicle against corrosion being carried out the selectivity exposure with being painted with corrosion-resisting pattern below 2.0 microns simultaneously; (4) implement the development treatment of employing aqueous alkali for the tunicle against corrosion after the exposure of described selectivity, in the operation of the corrosion-resisting pattern that to form pattern dimension on the described substrate simultaneously be the corrosion-resisting pattern used of the integrated circuit below 2.0 microns and size uses greater than 2.0 microns liquid-crystal display section; (5) wash the flushing operation that remains in the lip-deep developer solution of described corrosion-resisting pattern off.
12. the formation method of corrosion-resisting pattern according to claim 11 wherein, by adopting the exposure process of i line source, is carried out the operation of carrying out the selectivity exposure of described (3).
13. the formation method of corrosion-resisting pattern according to claim 11 wherein, is a exposure process under the low NA condition below 0.2 by NA, carries out the operation of carrying out the selectivity exposure of described (3).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002240791A JP2004077999A (en) | 2002-08-21 | 2002-08-21 | Forming method of positive photoresist composition for lcd manufacture with integrated circuit and liquid crystal display part formed on one substrate, and resist pattern |
| JP2002240791 | 2002-08-21 |
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|---|---|
| CN1484095A true CN1484095A (en) | 2004-03-24 |
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|---|---|---|---|
| CNA031543014A Pending CN1484095A (en) | 2002-08-21 | 2003-08-14 | Positive photoresist composition and method for forming slushing pattern |
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| JP (1) | JP2004077999A (en) |
| KR (1) | KR100596988B1 (en) |
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| JPH1010731A (en) * | 1996-06-25 | 1998-01-16 | Hitachi Chem Co Ltd | Negative photosensitive resin composition and production of resist image |
| KR100608966B1 (en) * | 1997-10-03 | 2006-09-22 | 제이에스알 가부시끼가이샤 | Radiation Sensitive Resin Composition |
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| JP2004077999A (en) | 2004-03-11 |
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