CN1519648A - Positive photo slushing compound compsn. for mfg. LCD, and forming method of slushing pattern - Google Patents
Positive photo slushing compound compsn. for mfg. LCD, and forming method of slushing pattern Download PDFInfo
- Publication number
- CN1519648A CN1519648A CNA2004100022100A CN200410002210A CN1519648A CN 1519648 A CN1519648 A CN 1519648A CN A2004100022100 A CNA2004100022100 A CN A2004100022100A CN 200410002210 A CN200410002210 A CN 200410002210A CN 1519648 A CN1519648 A CN 1519648A
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- China
- Prior art keywords
- lcd
- etching agent
- mentioned
- resist pattern
- positive light
- Prior art date
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- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- XLMBWGBLANISRF-UHFFFAOYSA-N OC1=C(C=C(C=C1CC1=CC(=C(C(=C1)C)O)C)CN)C Chemical compound OC1=C(C=C(C=C1CC1=CC(=C(C(=C1)C)O)C)CN)C XLMBWGBLANISRF-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- WXNRYSGJLQFHBR-UHFFFAOYSA-N bis(2,4-dihydroxyphenyl)methanone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O WXNRYSGJLQFHBR-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 1
- 229940109262 curcumin Drugs 0.000 description 1
- 235000012754 curcumin Nutrition 0.000 description 1
- 239000004148 curcumin Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- VFLDPWHFBUODDF-UHFFFAOYSA-N diferuloylmethane Natural products C1=C(O)C(OC)=CC(C=CC(=O)CC(=O)C=CC=2C=C(OC)C(O)=CC=2)=C1 VFLDPWHFBUODDF-UHFFFAOYSA-N 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229940035423 ethyl ether Drugs 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000001153 fluoro group Chemical class F* 0.000 description 1
- 229940074391 gallic acid Drugs 0.000 description 1
- 235000004515 gallic acid Nutrition 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000000113 methacrylic resin Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- VABBJJOSOCPYIT-UHFFFAOYSA-N methyl 2-methoxypropanoate Chemical class COC(C)C(=O)OC VABBJJOSOCPYIT-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010010 raising Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940124543 ultraviolet light absorber Drugs 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Images
Classifications
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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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
- C08L61/14—Modified phenol-aldehyde condensates
-
- 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
- G03F7/0226—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
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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
- G03F7/023—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
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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
- G03F7/023—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)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Photolithography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
Provided is a resist material for fabricating an LCD which forms a resist pattern with high resolution even under a low NA condition and has good linearity. A resist pattern is formed by using a positive photoresist composition characterized in that it contains (A)an alkali-soluble resin, (B)an esterification reaction product having an average esterification ratio of 30 to 90% comprising a low-molecular-weight novolac resin having a polystyrene-reduced mass average molecular weight of 300 to 1,300 and a naphthoquinone-diazide-sulfonic-acid compound, (C)a phenolic-hydroxyl-group-containing compound having a molecular weight of not more than 1,000, and (D)an organic solvent.
Description
Technical field
The present invention relates to LCD and make the formation method of using positive light anti-etching agent composition and resist pattern.
Background technology
Up to now, on glass substrate, form in the manufacturing of LCD liquid crystal display cells (LCD) partly, from viewpoint less expensive and that can form the good resist pattern of sensitivity, exploring degree and shape, often use the positive light anti-etching agent material of forming by the compound that contains novolac resin-benzoquinones diazido that in the manufacturing of semiconductor element, uses.
But, for example, with respect to the collar plate shape silicon wafer of 8 inches of the maximum gauges that in the manufacturing of semiconductor element, uses (about 200mm)～12 inches (about 300mm), in the manufacturing of LCD, even minimum is also used the tetragonal glass substrate of about 360mm * 460mm.
Like this, in the manufacturing field of LCD, much less the substrate of painting erosion resistant agent material is different at material and vpg connection, and from its big or small viewpoint, with differing widely of using in the manufacturing of semiconductor element.
Therefore, for LCD manufacturing anticorrosive additive material, requirement can form the good resist patterns of characteristic such as shape and size stability with respect to the substrate surface surface of broadness.
In addition, owing to consume very many anticorrosive additive materials in the manufacturing of LCD, for LCD manufacturing anticorrosive additive material, hope has aforesaid characteristic and is cheap.
Up to now, the anticorrosive additive material as LCD manufacturing usefulness has many reports (for example, following patent documentation 1-6).The anticorrosive additive material of putting down in writing among the patent documentation 1-6 is cheap, in addition, with respect to the small-sized substrate of for example about 360mm * 460mm, can form the resist pattern of coating, sensitivity, exploring degree, shape and size excellent in stability.Therefore, in the target of making more small-sized LCD, can suitably use.
[patent documentation 1]
Te Kaiping 9-160231 communique
[patent documentation 2]
Te Kaiping 9-211855 communique
[patent documentation 3]
The spy opens the 2000-112120 communique
[patent documentation 4]
The spy opens the 2000-131835 communique
[patent documentation 5]
The spy opens the 2000-181055 communique
[patent documentation 6]
The spy opens the 2001-75272 communique
But, in recent years, along with popularizing of the maximization of the display of PC and LCD TV etc., for more and more higher than the demand of also large-scale in the past LCD.In addition, owing to also require the low price etc. of LCD, require to improve the manufacturing efficient of LCD.
Therefore, in the manufacturing field of LCD, from the viewpoint of boost productivity (the processing quantity of time per unit) and processing controls, hope has the anticorrosive additive material of the sensitivity of about 30-50mJ.In addition,, wish to enlarge exposure area as much as possible, be at least about 100mm from the viewpoint of boost productivity (the processing quantity of time per unit)
2, usually, the manufacturing of preferred LCD uses that NA (numerical apertures of lens) is below 0.3, the exposure technology of the low NA condition below 0.2 particularly.
But, when using the exposure technology of low NA condition, made the anticorrosive additive material of usefulness for former LCD, under the low NA condition below 0.3 for example, be difficult to the good resist pattern of high-resolution landform forming shape.
That is, usually, the relational expression of exploring degree (the exploring explanation limit) shown in the following formula:
R＝k
1×λ/NA
[in the formula, R represents the exploring explanation limit, k
1The proportionality constant of resist or technology, image forming method is depended in expression, λ represents the light wavelength used in the exposure technology, NA represents the numerical aperture of lens] expression, by light source that uses the wavelength X weak point or the exposure technology of using high NA, can improve the exploring degree.For example, by using more short wavelength's i line (365nm) exposure to replace to improve the exploring degree with the photoetching process that the g line (436nm) that uses in the present LCD manufacturing exposes.
But in the manufacturing of LCD, as mentioned above, the high NAization that exposure area narrows down is not preferred, wishes to use the exposure technology under low NA condition.Therefore, be difficult to obtain high exploring degree.
In addition, now, as follow-on LCD, constantly carrying out on a glass substrate, that integrated circuit such as driver, DAC (digital simulation frequency converter), image processor, Video Controller, RAM parts forms simultaneously with the display part, for the technological development (Semiconductor FPD World 2001.9,50-67 page or leaf) of the high-performance LCD of so-called " system LCD "
At this moment, on substrate, owing to except the display part, also form the integrated circuit part, substrate has the tendency that maximizes more.Therefore, wish when making, to expose under the lower NA condition than common LCD.
In addition, in such system LCD, for example, be about 2-10 μ m with respect to the moulded dimension of display part, integrated circuit is partly formed by the small size of 0.5-2.0 μ m according to appointment.Therefore, preferably can form the small resist pattern of about 0.5-2.0 μ m, and wish that the exploring degree makes with the also high anticorrosive additive material of anticorrosive additive material than former LCD.
But, as mentioned above, be difficult because former LCD manufacturing forms with high-resolution ground under low NA condition with anticorrosive additive material, so be difficult to be used for the manufacturing of the LCD of system.For example under the low NA condition below 0.3, be difficult to form shape good, for example following small resist pattern of 2.0 μ m, and the resist pattern that obtains is not rectangle, and has the tendency that presents cone shape.
Specifically, for example open in the 2001-75272 communique, put down in writing the liquid crystal resist that contains alkali soluble resin and photonasty composition, do not contain sensitizer the spy.
But this liquid crystal is not suitable for the i line exposing, is difficult to be formed on the problems such as resist pattern below the 2.0 μ m that require in the manufacturing of the LCD of system with the resist existence.
Therefore, in the manufacturing process of the LCD of system, be fit to the i line exposing, even under the low NA condition 0.3 below for example, also hope can form the anticorrosive additive material of the good small resist pattern of shape.
Summary of the invention
Problem of the present invention provide have about 30-50mJ sensitivity, under low NA condition the exploring degree good, as the positive light anti-etching agent composition of the anticorrosive additive material that is fit to be manufactured on the LCD that forms integrated circuit and LCD part on the substrate and the formation method of resist pattern.
In order to solve above-mentioned problem, LCD positive light anti-etching agent composition of the present invention is characterized in that, comprises
(A) alkali soluble resin,
(B) polystyrene conversion matter average molecular weight is that the esterification yield low molecular weight novolak varnish gum of 300-1300 and naphthoquinones two nitrine sulfoacid compounds, average is the esterification reaction product of 30-90%,
(C) molecular weight is the compound that contains the phenol hydroxyl below 1000,
(D) organic solvent.
This LCD with positive light anti-etching agent composition preferably as i line exposing technology with the LCD positive light anti-etching agent composition.
In addition, being suitable as NA is that exposure technology below 0.3 is with the LCD positive light anti-etching agent composition.
In addition, be suitable as the LCD positive light anti-etching agent composition that the LCD that forms integrated circuit and LCD part on a substrate makes usefulness.
Also have, in explanation of the present invention, when being called the LCD of system, be meant " LCD that on a substrate, forms integrated circuit and LCD part ".
In addition, the formation method of resist pattern of the present invention is characterized in that, comprises
(1) positive light anti-etching agent composition of coating the invention described above on substrate, thus the operation of filming formed,
(2) heat treated (prebake) forms above-mentioned substrate of filming, and forms the operation of resist tunicle on substrate,
(3) to above-mentioned resist tunicle, use the mask of describing mask graph to select the operation of exposing,
(4) to the resist tunicle after the above-mentioned selection exposure, carry out the operation of heat treated (post exposurebake),
(5) to the resist tunicle after the above-mentioned heat treated, use the development treatment of aqueous alkali, thereby on above-mentioned substrate, form the operation of resist pattern,
(6) the flushing operation that will wash off at the developer solution of above-mentioned resist pattern remained on surface.
And, in the operation that above-mentioned (3) are selected to expose, as aforementioned mask, form the mask of using the mask graph both sides by having used the resist pattern of describing below the 2.0 μ m to form with mask graph and the resist pattern more than the 2.0 μ m, can form simultaneously in the operation of resist pattern in above-mentioned (5), on above-mentioned substrate, form the following integrated circuit of dimension of picture 2.0 μ m simultaneously and partly use resist pattern with resist pattern and the above LCD of 2.0 μ m.
In the preparation method of LCD of the present invention with positive light anti-etching agent composition and resist pattern, even owing under low NA condition, also can obtain excellent resolution, so be suitable as the manufacturing of the LCD of system.
Description of drawings
Fig. 1 is coated with positive light anti-etching agent composition on glass substrate, bake drying behind the graph exposure, is filled the key diagram of developer solution to Z from substrate end X in the developing apparatus with slit coater.
Embodiment
[LCD positive light anti-etching agent composition]
＜(A) composition 〉
(A) be alkali soluble resin.
(A) restriction especially of composition, can use be selected from the positive light anti-etching agent composition can be usually as tunicle form material any one or more than two kinds.
For example can enumerate, in the presence of acidic catalyst, carry out the novolac resin that condensation obtains by making phenols (phenol, metacresol, paracresol, xylenols, front three phenol etc.) and aldehydes (formaldehyde, formaldehyde precursor, propionic aldehyde, 2-hydroxy benzaldehyde, 3-hydroxy benzaldehyde, 4-hydroxy benzaldehyde etc.) and/or ketone (MEK, acetone etc.);
The hydroxy styrenes resinoid of the multipolymer of the multipolymer of the homopolymer of hydroxy styrenes or hydroxy styrenes and other styrene monomer, hydroxy styrenes and acrylic acid or methacrylic acid or its derivant etc.;
As the acrylic acid of the multipolymer of acrylic acid or methacrylic acid and its derivant or methacrylic resin etc.
By making phenols that contains metacresol and paracresol and the aldehydes that contains formaldehyde carry out the novolac resin that condensation obtains, be particularly suitable for the adjusting of the good anticorrosive additive material of high sensitivity and exploring degree.
(A) composition can be made according to conventional methods.
(A) the polystyrene conversion matter average molecular weight based on gel permeation chromatography of composition, though also according to its kind and difference, the viewpoint from sensitivity or figure form is 2000-100000, preferred 3000-20000.
＜(B) composition 〉
(B) composition is polystyrene conversion matter average molecular weight (the following M that abbreviates as sometimes
W) for the esterification yields low molecular weight novolak varnish gum of 300-1300 and naphthoquinones two nitrine sulfoacid compounds, average are the esterification reaction product of 30-90%, can select to use to belong to a kind of in these esterification reaction products or more than two kinds.In addition, polystyrene conversion matter average molecular weight is measured according to for example GPC.
As this low molecular weight novolak varnish gum, for example for the identical alkali-soluble novolac resin that in above-mentioned (A) composition, uses, can use resin that the matter average molecular weight is adjusted in the above-mentioned scope etc.
The M of this low molecular weight novolak varnish gum
WBe 300-1300, lower limit is preferably more than 350, and higher limit is preferably below 700.
By the matter average molecular weight is defined in this scope, can provide high sensitivity and exploring degree anticorrosive additive material good, that be suitable for the i line exposing technology under low NA condition.
The matter average molecular weight to be adjusted in the above-mentioned scope, for example can enumerate following three kinds of methods.
(i) can take out the low-molecular-weight district by using the known separate operation that low-molecular-weight district and high molecular are distinguished, obtain the M that the condensation reaction by desirable phenols and aldehydes and/or ketone obtains
WNovolac resin for about 2000-30000.
In addition, in the alkali-soluble novolac resin of (A) composition synthetic, the separate operation of using in order to select to take out the high molecular district is a technology general knowledge, and in order to obtain the separate operation of this low molecular weight novolak varnish gum, just select the different of taking-up, so also can be suitable for same operation to liking on this point of low-molecular-weight zone.
(ii) can pass through in the condensation reaction of desirable phenols and aldehydes and/or ketone, in course of reaction, the M of the condensation product in the sequentially determining reaction solution
W, work as M
WFinishing reaction during for the scope of 300-1300 obtains.
In addition, if the various raw materials, kind, its amount or the ratio of catalyzer, the reaction conditions (matching mechanism of solution concentration, temperature of reaction, various raw materials etc.) that use in synthetic are identical, if carry out the M in the primary first-order equation in advance
WMensuration, then when following synthetic same low molecular weight novolak varnish gum, only carry out the control in reaction time, just can obtain desirable M
W
(iii) can be by in the presence of acidic catalyst or base catalyst, desirable phenols and aldehydes and/or ketone being carried out condensation reaction, the low molecule phenolic compounds of Synthetic 2-4 nucleome or its dihydroxymethyl thing (being referred to as " phenol A "), and phenols that contains methylol or the phenols that does not contain methylol (being referred to as " phenol B ") are reacted with it obtain.
The control of the reaction needed of phenol A and phenol B makes Mw in 300～1300 scope, is for example undertaken by controlling the above-mentioned reaction time.
In addition, by in the solution of the high concentration that contains phenol A, add the solution of the low concentration that contains phenol B at every turn very micro-ly, can carry out above-mentioned control at an easy rate.
Also have, the ratio of phenols and aldehydes and/or ketone can suitably be adjusted according to the different of target compound and synthetic method, for example is 1: 1-2: 1 (mol ratio).
As (B) composition,, especially preferably contain more than one the material among following two kinds ((i), (ii)) from the viewpoint of effect.
(i) phenolic compounds by only using two functional groups uses aldehydes and/or ketone (only preferred formaldehyde) as the synthetic material of condensation agent as phenols.
(ii) the phenolic compounds of a phenolic compounds by only using two functional groups and a functional group uses aldehydes and/or ketone (only preferred formaldehyde) as the synthetic material of condensation agent as phenols.
Above-mentioned what is called " functional group " refers to the quantity in the hydrogen atom that upward exists with reactive site aldehydes and/or ketone (2,4,6) phenols (this hydrogen atom and aldehydes and/or ketone reaction).
The phenolic compounds of above-mentioned two functional groups is represented with following general formula (I).
(in the formula, R
1-R
5Be respectively hydrogen atom independently, the perhaps alkyl of carbon number 1-5, and R
1, R
3And R
5In two be hydrogen atom, one is the alkyl of carbon number 1-5.)
In the phenolic compounds of two functional groups, the alkyl of above-mentioned carbon number 1-5 (preferred 1-3, more preferably methyl) also can be straight chain, a chain.
In addition, at R
1, R
3And R
5In, the position that alkyl carries out combination does not have the branch of quality.
As the phenolic compounds of two functional groups, from the viewpoint of cheap and characteristic good, preferred orthoresol, paracresol, 2,5-xylenols, 3,4-xylenols, 2,3,5-pseudocuminol.
The phenolic compounds of an above-mentioned functional group is represented with following general formula (II).
(in the formula, R
11-R
15Be respectively hydrogen atom independently, the perhaps alkyl of carbon number 1-5, and R
11, R
13And R
15In one be hydrogen atom, two is the alkyl of carbon number 1-5.)
In the phenolic compounds of a functional group, the alkyl of above-mentioned carbon number 1-5 (preferred 1-3, more preferably methyl) also can be straight chain, a chain.
In addition, at R
11, R
13And R
15In, the position that alkyl carries out combination does not have the branch of quality.
As the phenolic compounds of a functional group, preferred 2 from the viewpoint of cheapness and characteristic good, 4-xylenols, 2,6-xylenols.
Also have, in above-mentioned (i), from the viewpoint of characteristic good, the phenolic compounds of two functional groups: aldehydes and/or ketone (preferred formaldehyde) are with 1: 1-2: 1 (mol ratio) used.
Above-mentioned (ii) in, from the viewpoint of characteristic good, the phenolic compounds of two functional groups: the phenolic compounds of a functional group is with 10: 1-1: 10, preferred 5: 1-1: 5 (mol ratios) are used.From the viewpoint of characteristic good, the total amount of phenols: aldehydes and/or ketone (preferred formaldehydes) are with 1: 1-2: 1 (mol ratio) used.
Method as synthetic above-mentioned low molecular weight novolak varnish gum (ii), the phenolic compounds solution that can be exemplified as 1. a functional group mixes with the dihydroxymethyl thing solution of the phenolic compounds of two functional groups that obtained by conventional method, carries out the method for condensation reaction in the presence of catalyzer; 2. the phenolic compounds solution with a functional group mixes with the phenolic compounds of two functional groups and the condensation reaction thing of aldehydes and/or ketone, carries out the method for condensation reaction etc. in the presence of catalyzer.
Above-mentionedly 1. be suitable for the synthetic low molecular weight novolak varnish gum that contains 3 following phenyl ring, above-mentionedly 2. be suitable for the synthetic low molecular weight novolak varnish gum that contains 4 above phenyl ring.
Secondly, the esterification by between this low molecular weight novolak varnish gum and the naphthoquinones two nitrine sulfoacid compounds can obtain the esterification reaction product that average esterification yield is 30-90% [(B) composition].
Naphthoquinones two nitrine sulfoacid compounds can use be selected from positive light anti-etching agent composition normally used any one or two or more.
For the not restriction especially of method of esterification, known reaction before can using.
For example, make naphthoquinones two nitrine sulfonyl chlorides and low molecular weight novolak varnish gum carry out condensation reaction.Specifically, can be by naphthoquinones-1 with ormal weight, 2-two nitrine-4 (perhaps 5)-sulfonyl chloride and low molecular weight novolak varnish gum are dissolved in organic solvents such as diox, n-methyl pyrrolidone, dimethyl acetamide, tetrahydrofuran, and make its reaction to base catalysts such as wherein adding triethylamine, triethanolamine, pyridine, alkali carbonate, alkali metal hydrogencarbonate, with the product that obtains wash, drying obtains.
The average esterification yield of the esterification reaction product that obtains like this is about 30-90%, preferably about 40-70%.By making average esterification yield is more than 30%, can form the resist pattern of excellent contrast.On the other hand, be below 90% by making average esterification yield, can prevent that sensitivity from descending.If average esterification yield surpasses 90%, can cause also sometimes that then sensitivity significantly descends, sometimes as LCD with positive light anti-etching agent composition, optimum decision system LCD with also being not suitable for.
The ratio of amount that can be by changing low molecular weight novolak varnish gum and naphthoquinones two nitrine sulfoacid compounds, the reaction time of esterification etc. are adjusted esterification yield.
Also have, the ratio of low molecular weight novolak varnish gum and naphthoquinones two nitrine sulfoacid compounds, from the viewpoints such as adjustment of esterification yield, naphthoquinones two nitrine sulfoacid compounds are the 0.3-0.9 mole with respect to 1 mole of hydroxyl in the low molecular weight novolak varnish gum, preferred 0.4-0.7 mole.
Also having, should (B) composition be so-called photonasty composition.
In positive light anti-etching agent composition of the present invention,, can also use other naphthoquinones two nitrine carboxylates that in positive light anti-etching agent composition, use usually except (B) composition.
Can also use for example phenolic compounds of polyhydroxy benzophenone or alkyl gallates etc. and the esterification reaction product of naphthoquinones two nitrine sulfoacid compounds etc.
But, never damage the viewpoint of effect of the present invention and set out, preferably their use amount is below the 50 quality % in containing all photonasty compositions of (B) composition, particularly below the 20 quality %.
In positive light anti-etching agent composition, preferably contain all combined amount of the photonasty composition of (B) composition, with respect to as alkali soluble resin of (A) composition and the total amount of following (C) composition, be 10-70 quality %, preferred 20-60 quality %.
And the combined amount of (B) composition is more than the 50 quality % in the photonasty composition, preferred 80-100 quality %.
Be defined as more than the lower limit by combined amount, can obtain the image of faithful to figure, can also improve replicability (B) composition.Be defined as below the higher limit by combined amount, can suppress sensitivity deterioration, in addition, can improve the homogeneity of the resist film that forms by positive light anti-etching agent composition, and can improve the exploring degree (B) composition.
＜(C) composition 〉
(C) composition preferably is the compound that contains the phenol hydroxyl of non-benzophenone class.Be somebody's turn to do (C) composition by using, it is obvious that sensitivity improves effect, even and in the i line exposing technology under low NA condition, also be high sensitivity, high-resolution, thereby can obtain to be suitable for the material of the LCD of system.
From the viewpoint of above-mentioned effect, the molecular weight of preferred (C) composition is below 1000, more preferably below 700, is essentially more than 200, and is preferred more than 300.
As (C) composition, the compound that contains the phenol hydroxyl that normally uses in the positive light anti-etching agent composition, if preferably satisfy the condition of above-mentioned molecular weight, then restriction especially can be selected to use a kind of arbitrarily or more than two kinds.And, wherein, shown in following general formula (IV),
[in the formula, R
31-R
38Represent hydrogen atom respectively independently, halogen atom, the alkyl of carbon number 1-6, the alkoxy of carbon number 1-6, the perhaps naphthenic base of carbon number 3-6; R
40, R
41Represent hydrogen atom respectively independently, perhaps the alkyl of carbon number 1-6; R
39Be hydrogen atom, perhaps during the alkyl of carbon number 1-6, Q is the alkyl of hydrogen atom, carbon number 1-6 or with the residue of following chemical formula (V) expression
(in the formula, R
42And R
43Represent hydrogen atom respectively independently, halogen atom, the alkyl of carbon number 1-6, the alkoxy of carbon number 1-6, the perhaps naphthenic base of carbon number 3-6; C represents the integer of 1-3), perhaps, Q be by with R
39End in conjunction with and and R
39And Q and R
39Between carbon atom form the group of the naphthenic base of carbochain 3-6 together; A, b represent the integer of 1-3; D represents the integer of 0-3; N represents the integer of 0-3]
In addition, when with Q and R
39Between carbon atom when forming the naphthenic base of carbochain 3-6 together, Q and R
39By combination, form the alkylidene of carbon number 2-5.
As the phenolic compounds that meets above-mentioned general formula (IV), 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-hydroxyl-2,5-3,5-dimethylphenyl)-2-hydroxy phenyl methane, two (4-hydroxyls-3, the 5-3,5-dimethylphenyl)-3,4-dihydroxy benzenes methylmethane, two (4-hydroxyl-2,5-3,5-dimethylphenyls)-3,4-dihydroxy benzenes methylmethane, two (4-hydroxyl-2,5-3,5-dimethylphenyls)-2,4-dihydroxy benzenes methylmethane, two (4-hydroxy phenyl)-3-methoxyl-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;
2,4-two (3,5-dimethyl-4-hydroxybenzyl)-5-hydroxyl phenol, 2,6-two (2,5-dimethyl-4-hydroxybenzyl)-4-methylphenol isoline type three nucleome oxybenzene compounds; 1, the different propane of 1-two [3-(2-hydroxy-5-methyl base benzyl)-4-hydroxyl-5-cyclohexyl phenyl], 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, two [3-(3,5-dimethyl-4-hydroxybenzyl)-and 4-hydroxy-5-methyl base phenyl] methane, two [3-(3,5-dimethyl-4-hydroxybenzyl)-and 4-hydroxyl-5-ethylphenyl] methane, two [3-(3,5-diethyl-4-hydroxybenzyl)-4-hydroxy-5-methyl base phenyl] methane, two [3-(3,5-diethyl-4-hydroxybenzyl)-and 4-hydroxyl-5-ethylphenyl] methane, two [2-hydroxyl-3-(3,5-dimethyl-4-hydroxybenzyl)-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, two [2,5-dimethyl-3-(2-hydroxy-5-methyl base benzyl)-4-hydroxy phenyl] methane isoline type four nucleome oxybenzene compounds; 2,4-two [2-hydroxyl-3-(4-hydroxybenzyl)-5-methyl-benzyl]-6-cyclohexylphenol, 2,4-two [4-hydroxyl-3-(4-hydroxybenzyl)-5-methyl-benzyl]-6-cyclohexylphenol, 2,6-two [2,5-dimethyl-3-(2-hydroxy-5-methyl base benzyl-4-hydroxybenzyl)-4-methylphenol isoline type five nucleome oxybenzene compound isoline type polyphenolic substances; 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)-and 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)-and 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-[1,1-two (4-hydroxy phenyl) ethyl] benzene, 1-[1-(3-methyl-4-hydroxy phenyl) isopropyl]-4-[1,1-two (3-methyl-4-hydroxy phenyl) ethyl] multinuclear branched chain type compound such as benzene; 1, condensed type oxybenzene compounds such as 1-two (4-hydroxy phenyl) cyclohexane etc.
These can be a kind of or be used in combination more than two kinds.
Wherein preferred 1-[1-(4-hydroxy phenyl) isopropyl]-4-[1,1-two (4-hydroxy phenyl) ethyl] benzene.
From the viewpoint of effect, (C) use level of composition is 10-70 quality % with respect to (A) composition, preferred 15-60 quality %.
＜(D) composition 〉
If (D) composition is the common compound that uses in the photo-corrosion-resisting agent composition, then not restriction especially, can select to use a kind of or more than two kinds, but the viewpoint of the good film thickness uniformity of the resist tunicle on good coating, the large glass substrate, preferred propylene-glycol monoalky lether acetic acid esters and/or contain the compound of lactic acid alkyl ester.
The propylene-glycol monoalky lether acetic acid esters is the compound with alkyl of the straight chain of carbon number 1-3 for example or a chain, wherein, in order to obtain the very good film thickness uniformity of the resist tunicle on the large glass substrate, also preferred especially propylene glycol monomethyl ether (the following PGMEA that abbreviates as sometimes).
As lactic acid alkyl ester, can enumerate methyl lactate, ethyl lactate (the following EL that abbreviates as sometimes) etc.Wherein, preferred ethyl lactate, but when the large glass substrate more than use 500mm * 600mm, exist to produce the irregular tendency of coating.Therefore, preferably use with mixed system with other solvent that suppresses this bad phenomenon.
From the viewpoint of above-mentioned effect, the combined amount of preferred propylene-glycol monoalky lether acetic acid esters is 20-100 quality % in (D) composition.
From the viewpoint of above-mentioned effect, the combined amount of preferred lactic acid alkyl ester is 20-100 quality % in (D) composition.
In addition, contain the two (D) composition of propylene-glycol monoalky lether acetic acid esters and lactic acid alkyl ester if use, then can obtain the resist pattern that film uniformity is good, shape is good of resist tunicle, even the viewpoint that produces from stable on heating improvement, inhibition scum silica frost also is preferred in addition.
Under the situation of the mixed system of propylene-glycol monoalky lether acetic acid esters and lactic acid alkyl ester,, by quality ratio, use the lactic acid alkyl ester that 0.1-10 doubly measures, preferred 1-5 doubly measures preferably with respect to the propylene-glycol monoalky lether acetic acid esters.
In addition, 2-heptanone (the following HE that abbreviates as sometimes) also is a preferred organic.Though not restriction especially, still, as mentioned above, the solvent that is fit to during the combination of the photonasty composition of right and wrong benzophenone class.
If the 2-heptanone is compared with PGMEA, then have to excellent heat resistance, reduce the characteristic of the resist composition that scum silica frost produces, be very preferred solvent.
From the viewpoint of above-mentioned effect, preferred 2-heptanone is 20-100 quality % in (D) composition.
Also have,, specifically, for example can be exemplified as following material as other organic solvent that can mix.
That is gamma-butyrolacton; The propylene glycol single-butyl ether; Ketones such as acetone, MEK, cyclohexanone, methyl isoamyl ketone; Ethylene glycol, propylene glycol, diglycol, ethylene glycol acetate, propylene glycol monoacetate, two sweet monoacetates or polyalcohols and derivants thereof such as their monomethyl ether, single ethylether, single propyl ether, single-butyl ether or single phenyl ether; Cyclic ethers class Ru diox; And ester class such as methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, ethyl pyruvate, methoxypropionic acid methyl esters, epoxy radicals ethyl propionate etc.
When using these solvents, wish it is below the 50 quality % in (D) composition.
In positive light anti-etching agent composition of the present invention, in the scope of not damaging the object of the invention, can make its some adjuvant that contains intermiscibility as required, for example for improve additional resin such as resist film performance, plastifier, preserving stabilizer, surfactant, for the image that makes development become more visible colorant, in order to make the sensitizer that the sensitization effect improves more or to prevent that halation is with adjuvants commonly used such as dyestuff, adaptation promoter.
As preventing the halation dyestuff, can use ultraviolet light absorber (for example 2,2 ', 4,4 '-tetrahydroxy benzophenone, 4-dimethylamino-2 ', 4 '-dihydric benzophenone, 5-amino-3-methyl isophthalic acid-phenyl-4-(4-hydroxy phenyl azo) pyrazoles, 4-dimethylamino-4 '-hydroxyazobenzene, 4-diethylamino-4 '-ethoxy azobenzene, 4-DEAB, curcumin etc.) etc.
Can add surfactant in order for example to prevent streak etc., can use for example FluoradFC-430, FC431 (trade name, Sumitomo 3M (strain) system), Eftop (EF122A, EF122B, EF122C, EF126 (trade name, ト-ケ system プ ロ ダ Network ッ (strain) system) fluorine class surfactant, R-08 (trade name, Dainippon Ink. ﹠ Chemicals Inc's system) etc. such as.
Positive light anti-etching agent composition of the present invention preferably can prepare by (A) composition, (B) composition, (C) composition and other composition as required are dissolved in (D) organic solvent.
Also have, (D) use amount of composition preferably can suitably be adjusted, so that with (A)-(C) composition and other composition dissolving of use as required, thereby obtains uniform positive light anti-etching agent composition.The preferred all solids constituent concentration that uses is 10-40 quality %, more preferably 20-30 quality %.
[the formation method of resist pattern]
Following table is shown in an example of the formation method that is fit to of resist pattern in the LCD manufacturing.
At first, with spinner etc. the positive light anti-etching agent composition of the invention described above is coated on the substrate and forms and film.The preferred glass substrate is as substrate.As glass substrate, use amorphous silicon usually, but in the field of the LCD of system, preferred low-temperature poly-silicon etc.As this substrate, because the exploring degree of positive light anti-etching agent composition of the present invention under low NA condition is good, so can use above, the above large-sized substrate of 550mm * 650mm particularly of 500mm * 600mm.
Then, form this substrate of filming and remove residual solvent, thereby form the resist tunicle in for example 100-140 ℃ of following heat treated (prebake).As the prebake method, preferably between electric hot plate and substrate, has the contiguous oven dry in gap.
In addition, for above-mentioned resist tunicle, use the mask of describing mask graph to select exposure.
As light source,, preferably use i line (365nm) in order to form small figure.In addition, the exposure technology of employing is that NA is, preferred below 0.2, the more preferably exposure technology of the low NA condition below 0.15 below 0.3 in preferred this exposure.
Then, the resist tunicle to after the selection exposure carries out heat treated (post exposurebake:PEB).As the PEB method, preferably between electric hot plate and substrate, has the contiguous oven dry in gap.
To the resist tunicle behind the above-mentioned PEB, if use the development treatment of the alkaline aqueous solution of developer solution, for example 1-10 quality % tetramethylammonium hydroxide aqueous solution, then solubilized is removed exposed portion, thereby forms the partly resist pattern of usefulness of resist pattern that integrated circuit uses and LCD on substrate simultaneously.
In addition, can form resist pattern by the developer solution of washing off at the resist pattern remained on surface with washing fluids such as pure water.
In the formation method of this resist pattern, when manufacturing system LCD, in the operation of carrying out above-mentioned selection exposure, as aforementioned mask, the resist pattern that preferred use is described below the 2.0 μ m forms the mask of using the mask graph both sides with mask graph and the above resist pattern formation of 2.0 μ m.
And, LCD of the present invention with positive light anti-etching agent composition because the exploring degree is good, so can obtain verily to reproduce the resist pattern of the small figure of mask graph.Therefore, form at the same time in the operation of above-mentioned resist pattern, can be on above-mentioned substrate, form the partly resist pattern of usefulness of the above LCD of resist pattern that the following integrated circuit of dimension of picture 2.0 μ m uses and 2.0 μ m simultaneously.
As mentioned above, positive light anti-etching agent composition of the present invention is suitable for the exposure technology under low NA condition.In addition, also be fit to i line exposing technology.Therefore, in the manufacturing of LCD, can obtain display resist pattern partly in high-resolution ground at least.
In addition, even because the exploring degree of positive light anti-etching agent composition of the present invention under low NA condition is also good, so can on a substrate, under same conditions of exposure, form coarse figure and fine figure.Therefore, even under low NA condition, also simultaneously high-resolution ground obtains the display part of the LCD of system and than its also small integrated circuit resist pattern partly, and is suitable as the manufacturing usefulness of the LCD of system.
With in the positive light anti-etching agent composition, from making viewpoints such as efficient raisings, throughput rate, preferred high sensitivityization is even also can obtain the material that can use for this point at LCD.
In addition, also have so-called scum silica frost and produce few effect.
In addition, if according to the formation method of the resist pattern of the present invention that uses the good above-mentioned positive light anti-etching agent composition of exploring degree under low NA condition, then can improve the throughput rate of LCD in making.
In addition, if according to the formation method of resist pattern of the present invention,, also can form the resist pattern of high-resolution even then in the exposure technology that is fit to the low NA condition that LCD makes.Especially, because can be forming resist pattern that the integrated circuit below the dimension of picture 2.0 μ m for example uses and for example resist pattern of usefulness partly of the LCD more than the 2.0 μ m on the substrate simultaneously, so can be suitable for the manufacturing of the LCD of system.
[embodiment]
Embodiment by following expression illustrates in further detail to the present invention, but the present invention is not limited to following examples.
[evaluation method of positive light anti-etching agent composition]
Below expression is for the evaluation method of following various rerum naturas (1)-(3) of the positive light anti-etching agent composition of following embodiment or comparative example.
(1) sensitivity evaluation:
Use large-scale square substrate (to install name: TR36000 with the resist-coating device, chemical industry (strain) system is answered in Tokyo) and in the glass substrate that forms the Cr film (after 550mm * 650mm) goes up the coating positive light anti-etching agent composition, the temperature of electric hot plate is set at 130 ℃, by separating the drying first time that about 1mm contiguous oven dry was at interval carried out 60 seconds, then the temperature of electric hot plate is set at 120 ℃, carry out 60 seconds the drying second time by separating about 0.5mm contiguous oven dry at interval, thereby form thickness 1.5 μ m resist tunicles.
Then, by describing to be useful on the capable and interval (L﹠amp of reproduction 3.0 μ m simultaneously; S) and 1.5 μ m L﹠amp; The test pattern mask (cross spider) of the mask graph of the resist pattern of S uses i line exposing device (device name: FX-702J, Nikon society system; NA=0.14), with can verily reproducing 3.0 μ m L﹠amp; The exposure of S (Eop amount) is selected exposure.
Then, with (the device name: TD-39000 デ モ machine of the developing apparatus with slit coater nozzle, chemical industry (strain) system is answered in Tokyo), pass through Y to Z from substrate end X as shown in Figure 1, the time that spends 10 seconds is filled 2.38 quality %TMAH aqueous solution, keeps washing 30 seconds after 55 seconds, by the drying that spins, on substrate, form 3.0 μ m L﹠amp simultaneously; The resist pattern of S and 1.5 μ m L﹠amp; The resist pattern of S.
At this moment above-mentioned Eop exposure as sensitivity, use the mJ unit representation.
(2) resolution evaluation:
Obtain the critical exploring degree in above-mentioned Eop exposure.
(3) scum silica frost evaluation:
In above-mentioned Eop exposure, describe 1.5 μ m L﹠amp with the SEM observation; The substrate surface of S is checked to have or not scum silica frost.The following symbolic representation of its evaluation result.
Zero: almost can not confirm the generation of scum silica frost.
: confirm to have produced a little the some scum silica frost.
*: confirm a large amount of scum silica frost that produce.
(embodiment 1)
Material conduct (A)-(D) composition that preparation is following.
(A) alkali-soluble novolac resin 100 mass parts
A1:, use 0.8 moles of formaldehyde by synthetic obtain, the M of conventional method with respect to 1 mole of mixed phenol of metacresol/paracresol (mol ratio 7/3)
W=6000, M
W/ M
n=4.0 novolac resin.
(B) esterification reaction product (PAC1/PAC3=2/1 (mass ratio))
30 mass parts
PAC1: the M that makes as the condensed polymer of gallic acid and acetone
WGallic acid-acetone resin of 1300 and 1, the esterification yield of 2-naphthoquinones two nitrine-5-sulfonic acid chloride (5-NQD) are 78% esterification reaction product.
PAC3: as 2,3,1 mole of two (2,3,5-trimethyl-4-hydroxy phenyl)-2-hydroxy phenyl methane (M (molecular weight)=376) that the condensation product of 6-pseudocuminol and 2-hydroxy benzaldehyde is made and the esterification yield of 2.02 moles of 5-NQD are 67.3% esterification reaction product.
(C) contain compound 20 mass parts of phenol hydroxyl
1-[1-(4-hydroxy phenyl) isopropyl]-4-[1,1-two (4-hydroxy phenyl) ethyl] benzene
(D) organic solvent
D1：PGMEA
With above-mentioned (A)-(C) composition and, with respect to the surfactant that the is equivalent to 350ppm (ProductName " R-08 " of these (A)-(C) composition gross masses; Big Japanese ink Industrial Co., Ltd system) is dissolved in as among the PGMEA of (D) composition, and adjust, so that solid constituent [(A)-(C) total amount of composition] concentration is 25-28 quality %, use the membrane filter of aperture 0.2 μ m that it is filtered, thus the preparation positive light anti-etching agent composition.
(embodiment 2-9), (comparative example 1-4)
Except the material that (B), (D) composition is replaced with record in the following table 1, prepare positive light anti-etching agent composition in the same manner with embodiment 1.
Table 1
| ????(B) | (D) (mass ratio) | ||
| Embodiment | ????1 | ????PAC1/PAC3(2/1) | ????PGMEA |
| ????2 | ????PAC2/PAC3(2/1) | ????PGMEA | |
| ????3 | ????PAC2/PAC3(1/2) | ????PGMEA | |
| ????4 | ????PAC1/PAC3(2/1) | ????EL | |
| ????5 | ????PAC1/PAC3(2/1) | ????EL/PGMEA(7/3) | |
| ????6 | ????PAC1/PAC3(2/1) | ????HE | |
| ????7 | ????PAC8/PAC3(2/1) | ????PGMEA | |
| ????8 | ????PAC9/PAC3(2/1) | ????PGMEA | |
| ????9 | ????PAC10/PAC3(2/1) | ????PGMEA | |
| Comparative example | ????1 | ????PAC4 | ????PGMEA |
| ????2 | ????PAC5 | ????PGMEA | |
| ????3 | ????PAC6 | ????PGMEA | |
| ????4 | ????PAC7 | ????PGMEA | |
In addition, in table 1, for (D) composition, so-called EL/PGMEA (7/3) expression mixes EL/PGMEA with mass ratio 7/3.
In addition, PAC2-10 as shown below.
PAC2: as 3-methyl-6-cyclohexylphenol and 3, that the condensation product of 4-4-dihydroxy benzaldehyde is made, 1 mole of two (2-methyl-4-hydroxyl-5-cyclohexyl phenyl)-3, the esterification yield of 4-dihydroxy benzenes methylmethane (M=500) and 2.11 moles of 5-NQD is 52.75% esterification reaction product.
PAC3: as 2,3,1 mole of two (2,3,5-trimethyl-4-hydroxy phenyl)-2-hydroxy phenyl methane (M=376) that the condensation product of 6-pseudocuminol and 2-hydroxy benzaldehyde is made and the esterification yield of 2.02 moles of 5-NQD are 67.3% esterification reaction product.
PAC4: as metacresol/paracresol/2,3, the M that the condensation product of 5-pseudocuminol=35: 40: 25 (mol ratio) and formaldehyde is made
W1500 novolac resin and the esterification yield of 5-NQD are 8% esterification reaction product.
The esterification yield of PAC5:1 mole two (2, the 4-dihydroxy phenyl) methane (M=232) and 3.76 moles of 5-NQD is 94% esterification reaction product.
The esterification yield of PAC6:1 mole three (4-hydroxy phenyl) methane (M=292) and 2 moles of 5-NQD is 66.7% esterification reaction product.
The esterification yield of PAC7:1 mole gallate and 3 moles of 5-NQD is 100% esterification reaction product.
PAC8: with 2,5-xylenols/paracresol (mol ratio 2/1) and formaldehyde are 1 mole 2 of the synthetic M=376 of raw material, and the esterification yield of 6-two (2,5-dimethyl-4-hydroxybenzyl)-4-methylphenol and 2 moles of 5-NQD is 66% esterification reaction product.
PAC9: with 2,6-xylenols/paracresol (mol ratio 2/1) and formaldehyde are 1 mole 2 of the synthetic M=376 of raw material, and the esterification yield of 6-two (3,5-dimethyl-4-hydroxybenzyl)-4-methylphenol and 2 moles of 5-NQD is 66% esterification reaction product.
PAC10: be 50% esterification reaction product with 2-cyclohexylphenol/paracresol (mol ratio 1/1) and formaldehyde/acetone (mol ratio 2/1) for the esterification yield of 1 mole of two [3-(2-hydroxy-5-methyl base benzyl)-4-hydroxyl-5-cyclohexyl phenyl] the different propane of the synthetic M=632 of raw material and 2 moles of 5-NQD.
Table 2
| (mJ) estimated in sensitivity | Resolution is estimated (μ m) | Scum silica frost is estimated | ||
| Embodiment | ????1 | ????30 | ????1.3 | ????○ |
| ????2 | ????30 | ????1.3 | ????○ | |
| ????3 | ????42.5 | ????1.2 | ????○ | |
| ????4 | ????35.0 | ????1.3 | ????○ | |
| ????5 | ????32.5 | ????1.3 | ????○ | |
| ????6 | ????37.5 | ????1.3 | ????○ | |
| ????7 | ????37.5 | ????1.1 | ????○ | |
| ????8 | ????40.0 | ????1.1 | ????○ | |
| ????9 | ????47.5 | ????1.3 | ????△ | |
| Comparative example | ????1 | ????30 | ????1.6 | ????× |
| ????2 | ????37.5 | ????1.5 | ????× | |
| ????3 | ????30 | ????1.5 | ????× | |
| ????4 | ????25 | ????1.6 | ????○ | |
Obtain the LCD high resolution of positive light anti-etching agent composition under low NA condition.
All good as the resolution formed by the visible embodiment of the result as shown in the table 2.
In addition, sensitivity also is being good aspect the degree that can use, and does not produce scum silica frost, thereby also is good material in these areas.
In contrast, because the molecular weight that comparative example 1 is formed is too high, so resolution is bad.Also produce scum silica frost in addition.
Because the esterification yield that comparative example 2 is formed has surpassed 90%, so resolution is bad.Also a little somewhat bad aspect scum silica frost in addition.
Because the molecular weight that comparative example 3 is formed is low, so resolution is bad.In addition, also produce scum silica frost.
Because the composition of comparative example 4 does not have the skeleton of low molecular weight novolak varnish gum, so sensitivity is too small, resolution is also poor.
The LCD of the present invention manufacture method of positive light anti-etching agent composition and resist pattern, owing under low NA condition, also can provide excellent resolution, thus be suitable as the manufacturing usefulness of the LCD of system, and industrial very useful.
Claims (13)
1. a LCD makes and uses positive light anti-etching agent composition, it is characterized in that, comprises
(A) alkali soluble resin,
(B) polystyrene conversion matter average molecular weight is that the esterification yield low molecular weight novolak varnish gum of 300-1300 and naphthoquinones two nitrine sulfoacid compounds, average is the esterification reaction product of 30-90%,
(C) molecular weight is the compound that contains the phenol hydroxyl below 1000,
(D) organic solvent.
2. LCD as claimed in claim 1 makes and uses positive light anti-etching agent composition, it is characterized in that described low molecular weight novolak varnish gum comprises by following general formula (I)
In the formula: R
1-R
5Be respectively hydrogen atom independently, the perhaps alkyl of carbon number 1-5, and
And R
1, R
3And R
5In two be hydrogen atom, one is the alkyl of carbon number 1-5, the phenolic compounds of two shown functional groups and the condensation reaction of aldehydes and/or ketone and the synthetic low molecular weight novolak varnish gum that obtains.
3. positive light anti-etching agent composition as claimed in claim 1 is characterized in that, described low molecular weight novolak varnish gum comprises by following general formula (I)
In the formula: R
1-R
5Be respectively hydrogen atom independently, the perhaps alkyl of carbon number 1-5, and R
1, R
3And R
5In two be hydrogen atom, one is the alkyl of carbon number 1-5, the phenolic compounds of two shown functional groups,
Following general formula (II)
In the formula: R
11-R
15Be respectively hydrogen atom independently, the perhaps alkyl of carbon number 1-5, and
And R
11, R
13And R
15In one be hydrogen atom, two is the alkyl of carbon number 1-5, the phenolic compounds of a shown functional group and the condensation reaction of aldehydes and/or ketone and the synthetic low molecular weight novolak varnish gum that obtains.
4. positive light anti-etching agent composition as claimed in claim 1 is characterized in that, described low molecular weight novolak varnish gum is included in following general formula (1)
In the formula: R
1-R
5Be respectively hydrogen atom independently, the perhaps alkyl of carbon number 1-5, and R
1, R
3And R
5In two be hydrogen atom, one is the alkyl of carbon number 1-5, the phenolic compounds of two shown functional groups and aldehydes and/or ketone synthesize in the condensation product that obtains by condensation reaction, make following general formula (II)
In the formula: R
11-R
15Be respectively hydrogen atom independently, the perhaps alkyl of carbon number 1-5, and
And R
11, R
13And R
15In one be hydrogen atom, two is the alkyl of carbon number 1-5, the reaction of the phenolic compounds of a shown functional group and the synthetic low molecular weight novolak varnish gum that obtains.
5. as each described positive light anti-etching agent composition among the claim 1-4, it is characterized in that above-mentioned (D) composition contains the propylene-glycol monoalky lether acetic acid esters.
6. positive light anti-etching agent composition as claimed in claim 1 is characterized in that, above-mentioned (D) composition contains lactic acid alkyl ester.
7. positive light anti-etching agent composition as claimed in claim 1 is characterized in that, above-mentioned (D) composition contains the 2-heptanone.
8. positive light anti-etching agent composition as claimed in claim 1 is characterized in that, is to use as i line exposing technology.
9. positive light anti-etching agent composition as claimed in claim 1 is characterized in that, is to be that exposure technology below 0.3 is used as NA.
10. positive light anti-etching agent composition as claimed in claim 1 is characterized in that, is to make as the LCD that forms integrated circuit and LCD part on a substrate to use.
11. the formation method of a resist pattern is characterized in that, comprises
(1) the described positive light anti-etching agent composition of coating claim 1 on substrate, thus the operation of filming formed,
(2) heat treated forms above-mentioned substrate of filming, and forms the operation of resist tunicle on substrate,
(3) to above-mentioned resist tunicle, use and to describe the following resist pattern of 2.0 μ m and form with the above resist pattern formation of mask graph and 2.0 μ m and select the operation of exposing with mask graph both sides' mask,
(4) to the resist tunicle after the above-mentioned selection exposure, carry out the operation of heat treated,
(5) to the resist tunicle after the above-mentioned heat treated, use the development treatment of aqueous alkali, thereby partly use the operation of resist pattern with resist pattern and the LCD more than the 2.0 μ m forming integrated circuit below the dimension of picture 2.0 μ m on the above-mentioned substrate simultaneously
(6) the flushing operation of washing off at the developer solution of above-mentioned resist pattern remained on surface.
12. the formation method of resist pattern as claimed in claim 11 is characterized in that, the operation that the selecting of above-mentioned (3) exposed is by using the i line to carry out as the exposure technology of light source.
13. the formation method of resist pattern as claimed in claim 11 is characterized in that, the operation that the selecting of above-mentioned (3) exposed is to be that exposure technology under the low NA condition below 0.3 is carried out by NA.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003024427A JP4101670B2 (en) | 2003-01-31 | 2003-01-31 | Positive photoresist composition for LCD production and method for forming resist pattern |
| JP2003024427 | 2003-01-31 |
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| Publication Number | Publication Date |
|---|---|
| CN1519648A true CN1519648A (en) | 2004-08-11 |
| CN1229690C CN1229690C (en) | 2005-11-30 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004100022100A Expired - Lifetime CN1229690C (en) | 2003-01-31 | 2004-01-15 | Positive photo slushing compound compsn. for mfg. LCD, and forming method of slushing pattern |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP4101670B2 (en) |
| KR (1) | KR100570948B1 (en) |
| CN (1) | CN1229690C (en) |
| TW (1) | TWI304918B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101034260B (en) * | 2006-03-08 | 2012-07-18 | 株式会社东进世美肯 | Photosensitive resin composition |
| CN111381444A (en) * | 2018-12-26 | 2020-07-07 | 东京应化工业株式会社 | Photosensitive resin composition, photosensitive dry film, patterned resist film, substrate with mold, and method for producing plated article |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4935269B2 (en) * | 2005-09-21 | 2012-05-23 | 東レ株式会社 | Positive photosensitive resin composition |
| JP2009222733A (en) * | 2008-01-25 | 2009-10-01 | Rohm & Haas Electronic Materials Llc | Photoresist comprising novolak resin blend |
| KR101430962B1 (en) * | 2008-03-04 | 2014-08-18 | 주식회사 동진쎄미켐 | Photoresist composition and method of manufacturing array substrate using the same |
| KR101632965B1 (en) * | 2008-12-29 | 2016-06-24 | 삼성디스플레이 주식회사 | Photoresist composition and method of fabricating thin film transistor substrate |
| CN101907827B (en) * | 2009-06-08 | 2011-11-23 | 奇美实业股份有限公司 | Positive-type photosensitive resin composition and protrusion for liquid crystal orientation control prepared from same |
| JP6138067B2 (en) * | 2014-02-03 | 2017-05-31 | ローム アンド ハース エレクトロニック マテリアルズ エルエルシーＲｏｈｍ ａｎｄ Ｈａａｓ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ ＬＬＣ | Photoresist containing novolac resin blend |
| CN107844028B (en) * | 2017-11-07 | 2021-04-30 | 潍坊星泰克微电子材料有限公司 | Photoresist, preparation method and photoetching process thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001051419A (en) | 1999-08-06 | 2001-02-23 | Jsr Corp | Radiation sensitive resin composition |
| JP2002278060A (en) | 2001-03-16 | 2002-09-27 | Jsr Corp | Radiation sensitive resin composition |
| JP4213366B2 (en) | 2001-06-12 | 2009-01-21 | Ａｚエレクトロニックマテリアルズ株式会社 | Method for forming thick film resist pattern |
-
2003
- 2003-01-31 JP JP2003024427A patent/JP4101670B2/en not_active Expired - Fee Related
-
2004
- 2004-01-15 CN CNB2004100022100A patent/CN1229690C/en not_active Expired - Lifetime
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101034260B (en) * | 2006-03-08 | 2012-07-18 | 株式会社东进世美肯 | Photosensitive resin composition |
| CN111381444A (en) * | 2018-12-26 | 2020-07-07 | 东京应化工业株式会社 | Photosensitive resin composition, photosensitive dry film, patterned resist film, substrate with mold, and method for producing plated article |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20040069994A (en) | 2004-08-06 |
| CN1229690C (en) | 2005-11-30 |
| TW200424764A (en) | 2004-11-16 |
| JP2004233846A (en) | 2004-08-19 |
| KR100570948B1 (en) | 2006-04-13 |
| JP4101670B2 (en) | 2008-06-18 |
| TWI304918B (en) | 2009-01-01 |
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