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CN1235090C - Positive photoresist composition and method for forming resist pattern - Google Patents

Positive photoresist composition and method for forming resist pattern Download PDF

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Publication number
CN1235090C
CN1235090C CNB031489958A CN03148995A CN1235090C CN 1235090 C CN1235090 C CN 1235090C CN B031489958 A CNB031489958 A CN B031489958A CN 03148995 A CN03148995 A CN 03148995A CN 1235090 C CN1235090 C CN 1235090C
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Prior art keywords
resist pattern
resist
composition
crystal display
substrate
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CN1469197A (en
Inventor
久保敦子
大内康秀
宫城贤
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Tokyo Ohka Kogyo Co Ltd
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Tokyo Ohka Kogyo Co Ltd
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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
    • G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
    • 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
    • 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
    • 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
    • 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
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
    • 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
    • G03F7/40—Treatment after imagewise removal, e.g. baking

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)

Abstract

A positive type photoresist composition for manufacturing a substrate on which an integrated circuit and a liquid crystal display part are formed together is characterized in that it is constituted by containing an alkali soluble resin (A), a naphthoquinonediazido ester (B), a phenolic hydroxyl group containing compound (C) having a specific structure and an organic solvent (D). A method for forming the resist pattern is characterized in that it includes a step for forming a resist coating film on the substrate by using the positive type resist composition and a step for performing selective exposure using a mask on which both of a mask pattern for forming the resist pattern for the integral circuit and a mask pattern for forming the resist pattern for the liquid crystal display part are drawn to simultaneously form the resist pattern for the integral circuit and the resist pattern for the liquid crystal display part.

Description

The formation method of positive light anti-etching agent composition and resist pattern
Technical field
The used positive light anti-etching agent composition and the formation method of resist pattern when the present invention relates to a kind of substrate that on making 1 substrate, forms integrated circuit and liquid-crystal display section.
Background technology
So far, in the manufacturing field of the liquid crystal display cells that for example adopts glass substrate, because relatively more cheap and can form the resist pattern of sensitivity, resolving power and shape excellence, the positive light anti-etching agent material that therefore compound systems that change the nitrogen base by novolac resin-contain quinone two that are used to make semiconductor element constitute more.
Yet with respect to the collar plate shape silicon wafer of 8 inches of maximum gauges (about 200mm)～12 inches (about 300mm) used in the semiconductor element manufacturing, what use in the manufacturing of liquid crystal display cells is that minimum is the rectangle glass substrate about 360mm * 460mm.
Like this, the size in the manufacturing field of liquid crystal display cells is extremely different with semiconductor element.
Therefore, in the anticorrosive additive material of liquid crystal display cells manufacturing usefulness, require on the whole base plate face, to form the resist pattern that shape and size have good stability.
As this liquid crystal display cells manufacturing photo anti-corrosion agent material, for example open flat 9-160231 communique, spy and open flat 9-211855 communique, spy and open 2000-112120 communique, spy and open 2000-131835 communique, spy and open 2000-181055 communique and spy and open many reports have been arranged in the 2001-75272 communique the spy.
These materials are cheap, and can form the resist pattern of coating, sensitivity, resolving power, shape and size excellent in stability for the more small-sized substrate about 360mm * 460mm, so are applicable in the manufacturing of the LCD that the display part is only arranged.
On the other hand, the technological development of high-performance LCD to the conduct next generation LCD that forms driver, DAC (digital analog converter), image processor, Video Controller, RAM (random access memory) integrated circuit of etc.ing and display part on 1 glass substrate just in vogue at present is (referring to Semiconductor FPD World 2001,9, pp.50-67).For convenience, in this instructions below this substrate that forms integrated circuit and liquid-crystal display section on 1 substrate is called the LCD of system.
Yet, among the described system LCD, with respect at for example display part pattern dimension about 2～10 μ m, need to form size at for example fine sizes integrated circuit patterns about 0.5～2.0 μ m, therefore when the occasion of these integrated circuit parts of formation under same conditions of exposure, wish its linearity [the mask resizing characteristic of same conditions of exposure (though the identical condition of the different exposures of the mask size on the reticle) when exposing down on the reticle] excellence with the display part.Also have,, also must improve the not available resolution of photo anti-corrosion agent material of used so far manufacturing used for liquid crystal display element in order to form the fine pattern of integrated circuit part.
If will improve resolution (resolving limit), Rayleigh described as follows (レ one リ) formula R=k 1(in the formula, R is a resolving limit to * λ/NA, k 1Be that λ is an employed light wavelength in the exposure-processed by photoresist or processing procedure, proportionality constant that formation method determined, NA is the numerical aperture of lens) shown in, need to use short wavelength's light source, or adopt the exposure-processed of high NA.
For this reason, when forming the above-mentioned for example fine resist pattern below the 2.0 μ m, change into from g line (436nm) exposure in past employing for example more the photoetching technique of short wavelength's i line (365nm) exposure will be more effective.
On the other hand, from improving the viewpoint of productive capacity (the processing quantity of unit interval), exposure area in the field of liquid crystals, wishing at least will be about 100mm2, if exposure area is big, keep the uniform plane of this part difficulty that just correspondingly becomes, and the shallow high NA lens of the depth of focus are no longer suitable, therefore are difficult to realize high NAization.
In view of above-mentioned reason, the general preferably low NA condition below 0.3 in the liquid crystal display cells manufacturing field, but, the photo anti-corrosion agent material that past uses in liquid crystal display cells is made, fine resist pattern about 0.5～2.0 μ m that is difficult to formation shape excellence under the low NA condition, the cross sectional shape of resist pattern and non-rectangle, and present tapered trend.
Thus, even be desirable to provide the system LCD manufacturing anticorrosive additive material of the rectilinearity excellence that under low NA condition, also can form fine resist pattern.
Summary of the invention
Therefore, the object of the present invention is to provide the anticorrosive additive material of the rectilinearity excellence that is suitable for making above-mentioned system LCD.
The inventor etc. have carried out research painstakingly for solving above-mentioned problem, found that, the positive light anti-etching agent composition that contains specific phenol hydroxyl compound, even under low NA condition, also can form fine resist pattern, be the anticorrosive additive material of rectilinearity excellence, use when being suitable for manufacturing system LCD, so that finished the present invention.
Promptly, used positive light anti-etching agent composition when the present invention relates to be manufactured on 1 substrate the substrate that forms integrated circuit and liquid crystal display cells part, it is characterized in that by (A) alkali soluble resins, (B) naphthoquinones two repeatedly nitrogen ester compounds, (C) with the compound that contains the phenol hydroxyl of following general formula (I) expression and (D) organic solvent constituted.
[changing 2]
And then resist pattern formation method of the present invention is characterised in that, comprising:
(1) above-mentioned positive light anti-etching agent composition be coated on formation is filmed on the substrate operation,
(2) carry out heat treated to being formed with above-mentioned substrate of filming, thus on substrate, form the resist tunicle operation,
(3) be used to form integrated circuit with the mask pattern of resist pattern be used to form the mask of liquid-crystal display section with being decorated with the mask pattern of resist pattern, to above-mentioned resist tunicle carry out the selectivity exposure operation,
(4) carry out development treatment with the resist tunicle of aqueous alkali after to above-mentioned selection exposure, with on aforesaid substrate, form simultaneously integrated circuit with resist pattern and liquid-crystal display section with the operation of resist pattern,
(5) rinsing process that residual developer solution on the above-mentioned resist patterned surfaces is washed off.
Description of drawings
Fig. 1 is in order to estimate rectilinearity, positive light anti-etching agent composition to be coated on the glass substrate, after toasting drying, pattern exposure, developer solution is coated onto the key diagram of Z with the developing apparatus with slit (slit) coating machine from substrate end X.
Embodiment
In positive light anti-etching agent composition of the present invention,, can from the material that positive light anti-etching agent composition, uses usually, select arbitrarily as tunicle formation material to as the not special restriction of the alkali soluble resins of composition (A).
As this alkali soluble resins, enumerated, for example, the novolac resin that in the presence of acidic catalyst, obtains of aldehydes such as phenol such as phenol, metacresol, paracresol, xylenols, front three phenol and formaldehyde, formaldehyde precursor, 2-hydroxy benzaldehyde, 3-hydroxy benzaldehyde, 4-hydroxy benzaldehyde through condensation; The hydroxy styrenes resinoids such as multipolymer of the multipolymer of the homopolymer of hydroxy styrenes or hydroxy styrenes and other styrenic monomers, hydroxy styrenes and acrylic or methacrylic acid or derivatives thereof; The alkali soluble resinss such as acrylic or methacrylic acid resin such as multipolymer of acrylic or methacrylic acid and its derivant.
Particularly, for the anticorrosive additive material of modulation sensitivity height and rectilinearity excellence, preferably by containing metacresol and 3, the phenol of 4-xylenols with contain the aldehydes of propionic aldehyde and formaldehyde through the resulting novolac resin of condensation reaction.
For the composition in the positive light anti-etching agent composition of the present invention (B) naphthoquinones two repeatedly the nitrogen ester compounds have no particular limits, the naphthoquinones two that can use as photographic composition from the resist in past is repeatedly selected for use arbitrarily in the nitrogen ester compounds, particularly, with the change carboxylate of nitrogen sulfoacid compound of the oxybenzene compound of following general formula (II) expression and naphthoquinones two, be suitable for photoetching process with the i line, also have, be adapted at forming for example occasion use of the fine resist pattern below the 2.0 μ m with excellent in shape.
Figure C0314899500081
[in the formula, R 1～R 8Represent the alkyl of hydrogen atom, halogen atom, carbon number 1～6, the alkoxy of carbon number 1～6 or the naphthenic base of carbon number 3～6 separately separately; R 10,, R 11Be separately the alkyl of hydrogen atom or carbon number 1～6 separately; Q is and R 9The end in conjunction with or not combination, Q not with R 9End in conjunction with the time, R 9Be the alkyl of hydrogen atom or carbon number 1～6, Q is the alkyl of hydrogen atom, carbon number 1～6 or the residue of representing with following chemical formula (III)
Figure C0314899500082
(in the formula, R 12And R 13Represent the alkyl of hydrogen atom, halogen atom, carbon number 1～6, the alkoxy of carbon number 1～6 or the naphthenic base of carbon number 3～6 separately separately; C represents 1～3 integer), and Q and R 9End in conjunction with the time, Q and R 9With Q and R 9Between carbon atom form the naphthenic base of carbochain 3～6 together; A, b represent 1～3 integer; D represents 0～3 integer; N represents 0～3 integer].
Be Q and R again 9With Q and R 9Between carbon atom when forming the naphthenic base of carbochain 3～6 together, Q and R 9In conjunction with the alkylidene that forms carbon number 2～5.
Enumerated as this oxybenzene compound that is equivalent in this general formula: 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, trisphenol type compounds such as 4-dihydroxy benzenes methylmethane;
Two (2,3,4-trihydroxy phenyl) methane, two (2, the 4-dihydroxy phenyl) methane, 2,3,4-trihydroxy phenyl-4 '-hydroxy phenyl methane, 2,4-two (3,5-dimethyl-4-hydroxybenzyl)-and 5-hydroxyl phenol, 2, linear 3 nuclear oxybenzene compounds such as two (2,5-dimethyl-4-the hydroxybenzyl)-4-methylphenols 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, linear 4 nuclear oxybenzene 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-, linear polyphenolic substances such as linear 5 nuclear oxybenzene compounds such as two [2,5-dimethyl-3-(2-hydroxy-5-methyl base benzyl)-4-the hydroxybenzyl]-4-methylphenols of 6-; 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, two (4-aminomethyl phenyl) ethyls of 1-]-4-[1-(4-hydroxy phenyl) isopropyl] benzene, 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-] multinuclear branching type compound such as benzene; 1, condensed type oxybenzene compounds such as 1-bis(4-hydroxyphenyl)cyclohexane etc.
Wherein, from forming sensitivity and excellent in resolution and the good resist pattern of shape, with two (5-cyclohexyl-4-hydroxy-2-methyl phenyl)-3,4-dihydroxy benzenes methylmethane, two (4-hydroxyl-2,3, the 5-trimethylphenyl)-and triphenol type compounds, 1 such as 2-hydroxy phenyl methane, linear 4 nuclear oxybenzene compounds such as two [3-(2-hydroxy-5-methyl base benzyl)-4-hydroxyl-5-cyclohexyl phenyl] different propane of 1-etc. are preferred.
Can with usual way come the phenol hydroxyl of the compound of above-mentioned general formula (II) expression all or part of be naphthoquinones two repeatedly nitrogen sulfonic acid esterifications, for example, can change compound condensation that nitrogen sulfonic acid chloride and above-mentioned general formula (II) represent and obtain by naphthoquinones two.Specifically, can be by compound and the naphthoquinones-1 that above-mentioned general formula (II) is represented, 2-two repeatedly nitrogen base-4 (or 5)-sulfonic acid chloride predetermined amounts is dissolved in the organic solvents such as dioxane, N-Methyl pyrrolidone, dimethyl acetamide, tetrahydrofuran, add base catalysts such as triethylamine, triethanolamine, pyridine, carbonic acid alkali metal salt, bicarbonate alkali metal salt therein, react, obtaining after resulting product washing, the drying.
As composition (B), except the naphthoquinones two of above-mentioned example repeatedly the nitrogen carboxylate, the naphthoquinones two that also can use other is the nitrogen carboxylate repeatedly, for example, oxybenzene compound such as polyhydroxy benzophenone or alkyl gallates and naphthoquinones two be the esterification reaction product etc. of nitrogen sulfoacid compound repeatedly, but, never undermines effect of the present invention, their consumption is preferably below 80 quality % of composition (B), particularly below 50 quality %.
In the positive light anti-etching agent composition of the present invention, the use level of composition (B) is with respect to 20～70% of the total amount of composition (A) and following compositions (C), serves as preferred with 30～50% mass ranges.When the use level of composition (B) when the lower limit of above-mentioned scope is following, can not get image strictly according to the facts in the pattern, have the anxiety of transcribing property decline.On the other hand, the use level of composition (B) exceeds going up in limited time of above-mentioned scope, and the homogeneity that sensitivity difference and formed resist film just might occur is low, the problem of resolution rate variance.
In the positive light anti-etching agent composition of the present invention, the maximum of composition (C) is characterised in that the compound that contains the phenol hydroxyl that has cooperated above-mentioned formula (I) represented.By cooperating such composition (C), can obtain the positive light anti-etching agent composition of rectilinearity excellence.Specifically, for example, can obtain being suitable for low NA condition (preferred below 0.3, more preferably 0.2 below) and be applicable to than the g line positive light anti-etching agent composition of short wavelength's i line exposing processing more.Can improve resolution by these two kinds of effects, its result becomes the resist composition that is suitable for being used to carry out the processing of i line exposing under the low NA condition that manufacturing system LCD uses.
With respect to composition (A) alkali soluble resins 100 mass parts, the use level of composition (C) is 5～50 mass parts, serving as preferred in 10～30 mass parts scopes.
To form in the following compositions (D) as organic solvent that solution uses serve as preferred to composition of the present invention so that composition (A)～(C) and the various adding ingredients that cooperate as required are dissolved in.
For organic solvent used among the present invention, not special restriction, but, and angle resist tunicle film thickness uniformity excellence on large-size glass substrate excellent from coating consider, serves as preferred to contain a kind of selecting at least from propylene-glycol monoalky lether acetic acid esters, lactic acid alkyl ester and 2-heptanone.
In the propylene-glycol monoalky lether acetic acid esters, for preferred especially, the film thickness uniformity of its resist tunicle on large-size glass substrate is very excellent with propylene glycol methyl ether acetate (being designated hereinafter simply as " PGMEA ").
Also have, in lactic acid alkyl ester, for most preferably, when using the above large-size glass substrate of 500mm * 600mm, might to cause being coated with the depth irregular in use separately with ethyl lactate, and therefore the mixed system of use and other solvent is advisable.
Particularly, containing the composition of propylene-glycol monoalky lether acetic acid esters and lactic acid alkyl ester, can form the thickness evenness excellence of resist tunicle, the resist pattern of shape excellence, is preferred therefore.
When mixing use propylene-glycol monoalky lether acetic acid esters and lactic acid alkyl ester, be advisable than the lactic acid alkyl ester that is 0.1～10 times of amount, preferred 1～5 times of amount with respect to propylene-glycol monoalky lether acetic acid esters fit quality.
Also have, also can use other organic solvent such as gamma-butyrolacton or propylene glycol monobutyl ether.When using gamma-butyrolacton, potpourri with use and propylene-glycol monoalky lether acetic acid esters serves as preferred, at this moment, with respect to the propylene-glycol monoalky lether acetic acid esters, fit quality than be 0.01～1 times of amount, preferably the gamma-butyrolacton in the scope of 0.05～0.5 times of amount is advisable.
Be also to use the organic solvent outside above-mentioned again.Ketones such as acetone, MEK, cyclohexanone, methyl isoamyl ketone for example, can have been enumerated; Ethylene glycol, propylene glycol, diethylene glycol, polyvalent alcohol and derivants thereof such as ethylene glycol acetate, propylene glycol monoacetate, diethylene glycol monoacetate or their monomethyl ethers, single ether, single propyl ether, monobutyl ether or monophenyl ether; The cyclic ethers class of dioxane and so on; And ester class such as methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, ethyl pyruvate, methoxypropionic acid methyl esters, ethoxyl ethyl propionate.
With these acetone equal solvents the time, with from propylene-glycol monoalky lether acetic acid esters, lactic acid alkyl ester and 2-heptanone, select more than a kind or the potpourri more than 2 kinds mix to use and be advisable.In this occasion, the consumption of described acetone equal solvent with respect to from propylene-glycol monoalky lether acetic acid esters, lactic acid alkyl ester and 2-heptanone, select more than a kind or the potpourri more than 2 kinds, below 50 quality %, be advisable.
In the scope that does not undermine purpose of the present invention, can use various adjuvants such as surfactant, ultraviolet absorber, preserving stabilizer among the present invention.
As surfactant, that can enumerate has, Off ロ ラ De FC-430, Off ロ ラ De FC-431 (trade name, the production of Sumitomo 3M company), エ Off ト Star プ EF122A, エ Off ト Star プ EF122B, エ Off ト Star プ EF122C, エ Off ト Star プ EF126 (trade name, ト-ケ system プ ロ ダ Network Star company production), メ ガ Off ア Star Network R-08 fluorochemical surfactants such as (trade names, big Japanese ink chemical company produces).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 '-hydroxyazobenzene, 4-diethylin-4 '-ethoxy azobenzene, 4-diethylin azobenzene, curcumin etc.
The example that the manufacturing system LCD that uses the present composition uses the ideal formation method of resist pattern is shown below.At first, composition (A), composition (B) and composition (C) and the various compositions that add as required be dissolved in the solvent as composition (D), with spin coater it is coated on the substrate.Preferably be used as substrate with glass substrate.This glass substrate can be above with 500mm * 600mm, the above large substrate of 550mm * 650mm particularly.
Secondly, this be formed with the substrate of filming for example 100～140 ℃ carry out heat treated (prebake conditions), remove remaining solvent, form the resist tunicle.As the method for prebake conditions, preferably carry out between electric hot plate and substrate, leaving the adjacency baking in space.
Then, with being decorated with the integrated circuit that is used to form (preferred 0.5～2.0 μ m) below 2.0 μ m fine pattern size for example with the mask pattern of resist pattern be used to form the mask of the liquid-crystal display section of the pattern dimension that surpasses 2.0 μ m (preferably below 10 μ m more than the 2.0 μ m), adopts required light source to carry out selectivity and expose with the mask pattern of resist pattern.For forming fine pattern, used here light source serves as preferred with i line (365nm), and the exposure-processed that its exposure is taked is treated to preferably with the low NA condition below NA0.3.
Then, the resist tunicle after the selectivity exposure is implemented development treatment, on substrate, form integrated circuit simultaneously with resist pattern and liquid-crystal display section resist pattern with aqueous alkali.Next it for example is immersed in 1～10 quality % tetramethylammonium hydroxide aqueous solution and so on aqueous alkali developer solution, the exposed portion dissolving is removed, just can obtain the image of faithful to mask pattern.Then, the developer solution that residues in the resist patterned surfaces is washed off, just can be formed the resist pattern with rinsing liquids such as pure water.
[embodiment]
Further describe the present invention with embodiment below.
The various rerum naturas of the embodiment that talks about later and the positive light anti-etching agent composition of comparative example are obtained as follows.
(1) linear evaluation
With spin coater sample coating at the glass substrate that is formed with the chromium film (on the 550mm * 650mm), electric plate temperature is adjusted to 130 ℃, according to the 1st drying of carrying out 60 seconds approximately every the adjacency baking of 1mm, then electric plate temperature is adjusted to 120 ℃, according to the 2nd drying of carrying out 60 seconds approximately every the adjacency baking of 0.5mm, formed the resist tunicle of thickness 1.5 μ m.
Next, be used to reproduce 3.0 μ m lines and interval (L﹠amp by being decorated with simultaneously; S) and 1.50 μ m L﹠amp; Test record paper (chart) mask (reticle) of each mask pattern of the resist pattern of S is with i line exposing device (device name: FX-702J, NIKON's manufacturing; NA=0.14) can faithful reappearance 3.0 μ mL﹠amp; Carried out the selectivity exposure under the exposure of S (Eop exposure).
Then, with 23 ℃, the tetramethylammonium hydroxide aqueous solution of 2.38 quality % at (device name: the TD-39000 machine of demonstrating of the developing apparatus with slot coated nozzle, Tokyo answers chemical industry company to make) in, as shown in Figure 1, from X through Y to Z, through 10 seconds liquid is coated on the substrate, and after keeping 55 seconds, washed 30 seconds, and be spin-dried for.
, with SEM (scanning electron microscope) photo observe the cross sectional shape of resulting resist pattern, estimate its 1.5 μ m L﹠amp thereafter; The repeatability of the resist pattern of S, the result is illustrated in the table 2.
(2) sensitivity evaluation
With the index that above-mentioned Eop exposure is estimated as sensitivity, the result is illustrated in the table 2.
(3) resolving power evaluation
Obtain the limiting resolution in the above-mentioned Eop exposure, the result is illustrated in the table 2.
(4) foaming (scum) is estimated
Under the Eop exposure, be decorated with 1.5 μ m L﹠amp with SEM (scanning electron microscope) observation; The substrate surface of S, whether investigation bubbles.
Can't see foaming person fully and represent with ◎, almost can not see foaming person and represent with zero, see that slightly foaming person represents with △, and foaming person's usefulness * expression takes place in a large number, the result is illustrated in the table 2.
(5) shape evaluation
Under above-mentioned Eop exposure, observe 1.5 μ m L﹠amp with SEM (scanning electron microscope); The resist pattern cross section of S is represented with ◎ when cross sectional shape is almost rectangle, sees slightly when film lacks and represents with zero, and taper person represents with △, and pattern is the scarce person's usefulness * expression of the most of film of curled hair shape and pattern.The result is illustrated in the table 2.
＜embodiment 1〉composition (A)
Alkali soluble resins (A1) 100 mass parts
A1: adopt metacresol/3, the mixing phenol of 4-biphenol=9/1 (mol than) and as the condensation material and the mixed aldehyde of propionic aldehyde/formaldehyde=1/3 of usefulness (mol than) according to the synthetic Mw=4750 of usual method, the novolac resin of Mw/Mn=2.44
Composition (B):
Naphthoquinones two is nitrogen carboxylate 40 mass parts repeatedly
(B1/B2＝1/1)
Two (2-methyl-4-hydroxyl-5-cyclohexyl phenyl)-3 of B1:1mol, 1 of 4-dihydroxy benzenes methylmethane and 2mol, 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 (2,3,5-trimethyl-4-the hydroxy phenyl)-2-hydroxy phenyl methane of B2:1mol and the 5-NQD of 2mol
Composition (C):
Contain phenol hydroxyl compound (C1) 25 mass parts
C1:1-[1, two (4-hydroxy phenyl) ethyls of 1-]-4-[1-(4-hydroxy phenyl) isopropyl] benzene
The surfactant メ ガ Off ア Star R-08 (trade name of mentioned component (A)～(C) with the 350ppm that is equivalent to composition (A)～(C) total quality, big Japanese ink company makes) be dissolved among the PGMEA, being modulated into solid constituent [total of composition (A)～(C)] concentration is 25～28 quality %, membrane filter with aperture 0.2 μ m filters, and is modulated into positive light anti-etching agent composition.
＜embodiment 2～9 〉,＜comparative example 1～4 〉
Except as composition (A)～(D), to press the described match ratio of table 1 and use outside the described material of table 1, all the other are modulated into positive light anti-etching agent composition similarly to Example 1.
Table 2 shows their evaluation result.Also have, because the positive light anti-etching agent composition of comparative example 4 is failed picture 1.5 μ m L﹠amp; Therefore the S pattern does not estimate its linearity.
Table 1
(A) (B) (match ratio) (C) (match ratio) (D)
Embodiment 1 A1 B1/B2(1/1) C1 (25 mass parts) PGMEA
2 A1 B3/B4(1/1) C1 (25 mass parts) PGMEA
3 A1 B1/B5(1/1) C1 (25 mass parts) PGMEA
4 A2 B1/B2(1/1) C1 (25 mass parts) PGMEA
5 A3 B1/B2(1/1) C1 (25 mass parts) PGMEA
6 A1 B1/B2(1/1) C1 (25 mass parts) NS
7 A1 B1/B2(1/1) C1 (25 mass parts) HE
8 A1 B1/B2(1/1) C1 (20 mass parts) PGMEA
9 A1 B1/B2(1/1) C1 (30 mass parts) PGMEA
Comparative example 1 A1 B1/B2(1/1) C2 (25 mass parts) PGMEA
2 A1 B1/B2(1/1) C3 (25 mass parts) PGMEA
3 A1 B1/B2(1/1) C4 (25 mass parts) PGMEA
4 A1 B1/B2(1/1) C5 (25 mass parts) PGMEA
The meaning of each symbol is as follows in the table 1:
A2: adopt metacresol/paracresol/2, the mixing phenol of 5-xylenols=4/2/4 (mol than) and as the condensation material and the formaldehyde of usefulness according to the synthetic Mw=5000 of usual method, the novolac resin of Mw/Mn=2.8
A3: adopt metacresol/paracresol/2,3, the mixing phenol of 5-three cresols=9/0.5/0.5 (mol than) and as the condensation material and the mixed aldehyde of formaldehyde/crotonaldehyde=2/1 of usefulness (mol than) according to the synthetic Mw=7000 of usual method, the novolac resin of Mw/Mn=3.05
1 of B3:1mol, the esterification reaction product of the 5-NQD of two [3-(2-hydroxy-5-methyl base benzyl)-4-hydroxyl-5-cyclohexyl phenyl] different propane of 1-and 2mol
2,3,4 of B4:1mol, the esterification reaction product of the 5-NQD of 4 '-tetrahydroxybenzophenone and 2.34mol
The esterification reaction product of the gallicin of B5:1mol and the 5-NQD of 3mol
C2: two (3,5-dimethyl-4-hydroxy phenyl)-3,4-dihydroxy benzenes methylmethane
C3: two (4-hydroxy phenyl)-4-hydroxy phenyl methane
C4: two (2,3,5-trimethyl-4-hydroxy phenyl)-2-hydroxy phenyl methane
C5: two [3-(3,5-dimethyl-4-hydroxybenzyl)-4-hydroxy-5-methyl base phenyl] methane
PGMEA: propylene glycol methyl ether acetate
NS: 9/1 (mol ratio) mixed liquor of ethyl lactate and butyl acetate
The HE:2-heptanone
Table 2
Linear evaluation (μ m) Sensitivity is estimated (mJ) Resolution is estimated (μ m) Bubble and estimate Shape evaluation
Embodiment 1 1.50 45 1.3 ◎ ◎
2 1.60 50 1.3 ○ ◎
3 1.52 60 1.3 △ ○
4 1.62 43 1.3 ○ ○
5 1.57 45 1.3 △ ○
6 1.49 60 1.3 ○ ○
7 1.65 68 1.3 ○ ○
8 1.68 53 1.3 ○ △
9 1.4 30 1.3 △ △
Comparative example 1 2.02 45 1.4 △ △
2 1.85 35 1.4 △ △
3 1.91 70 1.4 ○ △
4 - 60 1.7 × ×
As shown in Table 2, in the positive light anti-etching agent composition of comparative example, except not estimating its linear person because of failing the picture case, the rectilinearity evaluation result of the pattern of gained is all more than 1.85 μ m.Shape also be △～*, resolution is also more than 1.4 μ m.In contrast, the linear evaluation of the pattern of positive light anti-etching agent composition of the present invention has obtained linear excellent pattern below 1.68 μ m and be bordering on 1.50 μ m.Also have, resolution is 1.3 μ m, also demonstrates the resolution more more excellent than comparative example.
In addition, sensitivity, resolving power, foaming evaluation, shape evaluation are all good as can be known, comprise that all assessment items of rectilinearity have reached good balance.
As above explanation, the present invention can provide can obtain linear excellent pattern, used good positive light anti-etching agent composition when being manufactured on 1 substrate the substrate (system LCD) that forms integrated circuit and liquid-crystal display section.In addition, form the fine resist pattern that method can form linear excellence and be suitable for manufacturing system LCD by resist pattern of the present invention.

Claims (11)

1. contain (A) alkali soluble resins, with respect to (A) composition and (C) the total quality of composition be 20-70% (B) naphthoquinones two repeatedly the nitrogen ester compounds, with respect to (A) compositions of 100 mass parts be (C) of 5-50 mass parts with the compound that contains the phenol hydroxyl of following general formula (I) expression,
Figure C031489950002C1
And (D) positive light anti-etching agent composition of organic solvent, on 1 substrate, form the purposes in the manufacturing of substrate of integrated circuit and liquid-crystal display section.
2. purposes as claimed in claim 1 is characterized in that, described (D) composition contain from propylene-glycol monoalky lether acetic acid esters, lactic acid alkyl ester and 2-heptanone, select more than a kind.
3. purposes as claimed in claim 1 is characterized in that, described positive light anti-etching agent composition is used for the i line exposing to be handled.
4. purposes as claimed in claim 1 is characterized in that, described positive light anti-etching agent composition is that to be used for numerical aperture be exposure-processed below 0.3.
5. purposes as claimed in claim 1 is characterized in that, the resist pattern that is used to form integrated circuit is the resist pattern of live width below 2.0 μ m, and liquid crystal display is the resist pattern that live width surpasses 2.0 μ m with the resist pattern.
6. the formation method of a resist pattern is characterized in that comprising:
(1) contain (A) alkali soluble resins, with respect to (A) composition and (C) the total quality of composition be 20-70% (B) naphthoquinones two repeatedly the nitrogen ester compounds, be (C) of 5-50 mass parts compound that contains the phenol hydroxyl with respect to (A) compositions of 100 mass parts with following general formula (I) expression.
Figure C031489950003C1
And (D) the positive light anti-etching agent composition positive light anti-etching agent composition of organic solvent is coated on the substrate and forms the operation of filming;
(2) carry out heat treated to being formed with above-mentioned substrate of filming, on substrate, form the operation of resist tunicle;
(3) use is decorated with and is used to form integrated circuit with the mask pattern of resist pattern and the mask of the mask pattern that is used to form liquid-crystal display section usefulness resist pattern, and above-mentioned resist tunicle is carried out the operation that selectivity is exposed;
(4) carry out development treatment with the resist tunicle of aqueous alkali after, on aforesaid substrate, to form integrated circuit simultaneously with resist pattern and liquid-crystal display section operation with the resist pattern to the exposure of above-mentioned selectivity; With
(5) wash the rinsing process that remains in the developer solution on the above-mentioned resist patterned surfaces off.
7. the formation method of the resist pattern described in claim 6 is characterized in that described (3) carry out the operation of selectivity exposure is to be undertaken by the exposure-processed that is light source with the i line.
8. the formation method of the resist pattern described in claim 6 or 7 is characterized in that described (3) carry out the operation of selectivity exposure is by being that exposure-processed under the low numerical aperture condition below 0.3 is carried out in numerical aperture.
9. the formation method of the resist pattern described in claim 6 is characterized in that the integrated circuit in described (4) operation is the resist pattern of live width below 2.0 μ m with the resist pattern.
10. the formation method of the resist pattern described in claim 6 is characterized in that the liquid crystal display in described (4) operation is the resist pattern that live width surpasses 2.0 μ m with the resist pattern.
11. the formation method of resist pattern according to claim 6, integrated circuit in described (4) operation is the resist pattern of live width below 2.0 μ m with the resist pattern, and liquid crystal display is the resist pattern that live width surpasses 2.0 μ m with the resist pattern.
CNB031489958A 2002-07-11 2003-07-03 Positive photoresist composition and method for forming resist pattern Expired - Fee Related CN1235090C (en)

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