WO2023007941A1 - 特定の共重合体を含むポジ型感光性樹脂組成物 - Google Patents
特定の共重合体を含むポジ型感光性樹脂組成物 Download PDFInfo
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- WO2023007941A1 WO2023007941A1 PCT/JP2022/022110 JP2022022110W WO2023007941A1 WO 2023007941 A1 WO2023007941 A1 WO 2023007941A1 JP 2022022110 W JP2022022110 W JP 2022022110W WO 2023007941 A1 WO2023007941 A1 WO 2023007941A1
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- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical group FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- XKYICAQFSCFURC-UHFFFAOYSA-N isoamyl formate Chemical compound CC(C)CCOC=O XKYICAQFSCFURC-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940024423 isopropyl isobutyrate Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GHDIHPNJQVDFBL-UHFFFAOYSA-N methoxycyclohexane Chemical compound COC1CCCCC1 GHDIHPNJQVDFBL-UHFFFAOYSA-N 0.000 description 1
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 1
- VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 description 1
- IBKQQKPQRYUGBJ-UHFFFAOYSA-N methyl gallate Natural products CC(=O)C1=CC(O)=C(O)C(O)=C1 IBKQQKPQRYUGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GXMIHVHJTLPVKL-UHFFFAOYSA-N n,n,2-trimethylpropanamide Chemical compound CC(C)C(=O)N(C)C GXMIHVHJTLPVKL-UHFFFAOYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- GSGDTSDELPUTKU-UHFFFAOYSA-N nonoxybenzene Chemical compound CCCCCCCCCOC1=CC=CC=C1 GSGDTSDELPUTKU-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- JZZRXECTAQPLNI-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O.CCCCC=O JZZRXECTAQPLNI-UHFFFAOYSA-N 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- LYKRPDCJKSXAHS-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical class OC1=C(O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1O LYKRPDCJKSXAHS-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- KIWATKANDHUUOB-UHFFFAOYSA-N propan-2-yl 2-hydroxypropanoate Chemical compound CC(C)OC(=O)C(C)O KIWATKANDHUUOB-UHFFFAOYSA-N 0.000 description 1
- GVIIRWAJDFKJMJ-UHFFFAOYSA-N propan-2-yl 3-oxobutanoate Chemical compound CC(C)OC(=O)CC(C)=O GVIIRWAJDFKJMJ-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- DHGFMVMDBNLMKT-UHFFFAOYSA-N propyl 3-oxobutanoate Chemical compound CCCOC(=O)CC(C)=O DHGFMVMDBNLMKT-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 125000005372 silanol group Chemical group 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-Butyl ethyl ether Natural products CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
- IXXMVXXFAJGOQO-UHFFFAOYSA-N tert-butyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OC(C)(C)C IXXMVXXFAJGOQO-UHFFFAOYSA-N 0.000 description 1
- KVWOTUDBCFBGFJ-UHFFFAOYSA-N tert-butyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC(C)(C)C KVWOTUDBCFBGFJ-UHFFFAOYSA-N 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- TWBUVVYSQBFVGZ-UHFFFAOYSA-N tert-butyl butanoate Chemical compound CCCC(=O)OC(C)(C)C TWBUVVYSQBFVGZ-UHFFFAOYSA-N 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
-
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/22—Exposing sequentially with the same light pattern different positions of the same surface
-
- 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
- G03F7/30—Imagewise removal using liquid 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
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
Definitions
- the present invention relates to a positive photosensitive resin composition, a cured film obtained from the resin composition, a microlens, and a method for producing the same.
- Imaging devices such as CCD image sensors and CMOS image sensors, or display devices such as liquid crystal displays and organic EL displays, often use minute lenses called microlenses to improve performance.
- microlenses For example, providing the image sensor with microlenses has the effect of improving the light collection rate and enhancing the sensor sensitivity.
- An etch-back method is known as one of methods for manufacturing microlenses (for example, Patent Document 1). Specifically, a microlens resin layer is formed on a color filter, a positive resist is applied on the resin layer, a part of the resist is exposed and developed, and a lens pattern is formed by heating as necessary. Then, by etching back using the lens pattern as an etching mask, the lens pattern shape is transferred to the microlens resin layer to fabricate the microlens.
- the positive resist as it is as a microlens.
- the formed microlens has excellent transparency and chemical resistance.
- a flexible resin composition is required.
- the shape of the microlens differs depending on the design of the device, and various shapes such as a prism, a cylinder, a truncated pyramid, a truncated cone, and a truncated cone may be required.
- Patent Document 2 proposes a photosensitive resin composition containing an alkali-soluble copolymer and a quinonediazide group-containing compound.
- a microlens can be obtained by forming a resin pattern by exposure and development, and then crosslinking phenolic hydroxy groups and epoxy groups by heating.
- Patent Document 3 proposes a radiation-sensitive resin composition containing, in addition to an alkali-soluble copolymer and a 1,2-quinonediazide compound, a compound that generates an acid upon exposure to radiation.
- a strong acid can be generated inside the resin pattern by re-exposing the resin pattern, and cationic polymerization can proceed, so that the temperature of the process can be lowered.
- the monomer forming the alkali-soluble copolymer used in the composition contains a carboxylic acid or a carboxylic acid anhydride, and there is a possibility that a residue may be generated during patterning of the copolymer. If a part of the resin remains in the spaces between patterns, the characteristics of the device are seriously adversely affected, so there is a demand for a photosensitive resin composition that enables positive patterning without leaving any residue.
- Patent Document 4 proposes a radiation-sensitive resin composition containing an acid-generating compound with a pKa of 4.0 or less in addition to an alkali-soluble polymer and a quinonediazide compound.
- the organic devices and flexible devices must have reliability that can withstand practical use.
- There is a demand for a photosensitive resin composition that does not deteriorate even after the step is performed and that enables the production of microlenses having good performance.
- the present invention has been made based on the above circumstances, and an object of the present invention is to enable positive patterning without residue and to obtain a microstructure having a desired spherical or hemispherical shape even in a low-temperature process of 130° C. or less.
- a first aspect of the present invention is a positive photosensitive resin composition containing the following (A) component, the following (B) component, the following (C) component, and a solvent.
- a copolymer containing no carboxy group or carboxylic acid anhydride group Component (B): quinonediazide compound
- the (a2) epoxy ring-containing monomer is, for example, a monomer represented by the following formula (2), and the (a3) hydroxy group-containing monomer having an acid dissociation constant pKa of 14 or more is, for example, the following formula It is a monomer represented by (3).
- R 0 represents a hydrogen atom or a methyl group
- R 3 represents a divalent organic group represented by the following formula (I)
- R 4 represents the following formula (4) or the following formula (5).
- R 5 represents a monovalent organic group represented by the following formula (I').) (Wherein, c represents an integer of 0 to 3, d represents an integer of 1 to 3, e independently represents an integer of 2 to 6, * represents the above formula (2) or the above formula (3) Represents a bond with the alkenyl group of the monomer represented by represents a bond with the monovalent organic group represented by the above formula (4) or (5).)
- the component (A) is, for example, a copolymer having a structural unit represented by the following formula (1a), a structural unit represented by the following formula (2a), and a structural unit represented by the following formula (3a).
- R 0 each independently represents a hydrogen atom or a methyl group
- R 1 represents a single bond or an alkylene group having 1 or 2 carbon atoms
- R 2 represents a methyl group
- b represents 0 to 2 represents an integer
- R 4 represents a monovalent organic group represented by the following formula (4) or (5)
- e represents an integer of 2 to 6.
- the polystyrene equivalent weight average molecular weight of component (A) is, for example, 5,000 to 30,000.
- the component (C) is, for example, a nonionic photoacid generator.
- the nonionic photoacid generator is, for example, a photoacid generator represented by the following formula (6).
- R 6 represents a hydrocarbon group or perfluoroalkyl group having 1 to 10 carbon atoms
- R 7 represents a linear alkyl group or alkoxy group having 1 to 8 carbon atoms
- 3 carbon atoms represents a branched alkyl group or alkoxy group of 1 to 8.
- the positive photosensitive resin composition of the present invention may further contain the following component (D).
- the positive photosensitive resin composition of the present invention may further contain the following component (E).
- the positive photosensitive resin composition of the present invention is for microlens production, for example.
- a second aspect of the present invention is a cured film obtained from the positive photosensitive resin composition.
- a third aspect of the present invention is a microlens produced from the positive photosensitive resin composition.
- a fourth aspect of the present invention includes a coating step of coating the positive photosensitive resin composition on a substrate to form a resin film, and a first exposure step of exposing at least a portion of the resin film after the coating step. a developing step of removing the exposed portion of the resin film with a developer after the first exposure step to form a pattern of the unexposed portion of the resin film; and a second exposure of further exposing the pattern after the developing step. and a post-baking step of heating the pattern at a temperature of 130° C. or less after the second exposure step.
- a reflow step of heating the pattern at a temperature of 130° C. or less may be included.
- the base material is, for example, a substrate on which a color filter is formed.
- the specific copolymer (A) component, the quinonediazide compound (B) component, and the photoacid generator (C) component are included at the same time, positive patterning is possible without residue.
- a microlens having a desired spherical or hemispherical shape can be formed even by a low-temperature process of 130°C or less, and the formed microlens has excellent transparency, chemical resistance and long-term reliability;
- a positive photosensitive resin composition can be provided.
- the positive photosensitive resin composition of the present invention will be described in more detail.
- the (A) component contained in the positive photosensitive resin composition of the present invention includes (a1) a monomer represented by the following formula (1), (a2) a monomer containing an epoxy ring, and (a3) an acid dissociation constant It is a copolymer of a monomer containing a hydroxyl group with a pKa of 14 or more and does not contain a carboxyl group and a carboxylic acid anhydride group.
- the carboxylic anhydride group is a divalent group represented by -CO-O-CO-.
- R 0 represents a hydrogen atom or a methyl group
- R 1 represents a single bond or an alkylene group having 1 or 2 carbon atoms
- R 2 represents a methyl group
- a represents 1 or 2
- b represents an integer from 0 to 2.
- Examples of the monomer represented by formula (1) include N-(2-hydroxyphenyl)(meth)acrylamide, N-(3-hydroxyphenyl)(meth)acrylamide, N-(4-hydroxy Phenyl)(meth)acrylamide, N-(4-hydroxybenzyl)(meth)acrylamide, N-(4-hydroxyphenethyl)(meth)acrylamide, N-(3,5-dimethyl-4-hydroxyphenyl)(meth) Acrylamide, N-(3,5-dimethyl-4-hydroxybenzyl)(meth)acrylamide, and N-(3,5-dimethyl-4-hydroxyphenethyl)(meth)acrylamide. These monomers may be used individually by 1 type, or may be used in combination of 2 or more type.
- the ratio of the monomer represented by the formula (1) is 5 parts by mass to 60 parts by mass, preferably 100 parts by mass of the monomers (a1), (a2) and (a3). 8 to 50 parts by mass, more preferably 10 to 40 parts by mass.
- the (a2) epoxy ring-containing monomer is a monomer having at least one epoxy ring in the molecule, and specific examples thereof include monomers represented by the following formulas (2-1) to (2-16). is mentioned. These monomers may be used individually by 1 type, or may be used in combination of 2 or more type.
- the ratio of the epoxy ring-containing monomer is 20 to 80 parts by mass, preferably 30 to 80 parts by mass, per 100 parts by mass of the monomers (a1), (a2) and (a3). 70 parts by mass, more preferably 40 to 60 parts by mass.
- the monomer containing a hydroxy group with an acid dissociation constant pKa of 14 or more is a monomer having at least one hydroxy group with an acid dissociation constant pKa (the lowest value in the case of polyvalent acids) of 14 or more.
- Specific examples thereof include monomers represented by the following formulas (3-1) to (3-25).
- the monomer does not contain functional groups with an acid dissociation constant pKa of 13 or less, such as silanol groups, fluoroalcohol groups, maleimide groups, carboxy groups, and phenolic hydroxy groups. These monomers may be used individually by 1 type, or may be used in combination of 2 or more type.
- the ratio of the monomer containing a hydroxy group having an acid dissociation constant pKa of 14 or more is 5 parts by mass to 60 parts by mass with respect to 100 parts by mass of the monomers of (a1), (a2) and (a3). Parts by mass, preferably 8 to 50 parts by mass, more preferably 10 to 40 parts by mass.
- the weight average molecular weight of component (A) is 5,000 to 30,000, preferably 5,000 to 20,000, more preferably 5, as polystyrene equivalent weight average molecular weight MW calculated by gel permeation chromatography (GPC). ,000 to 15,000.
- GPC gel permeation chromatography
- Component (A) has a glass transition temperature of 70°C to 130°C. By setting the glass transition temperature of the component (A) within the above range, it has good reflow properties even in a low-temperature process of 130° C. or less, and a desired spherical or hemispherical microlens can be produced. .
- the component (B) contained in the positive photosensitive resin composition of the present invention is not particularly limited as long as it is a compound having a 1,2-quinonediazide group.
- Condensates with sulfonic acid halides can be used. Specifically, 10 mol% to 100 mol%, preferably 20 mol% to 95 mol%, of the hydroxy groups of the hydroxy group-containing compound are esterified with the 1,2-naphthoquinonediazide sulfonic acid halide. compounds can be used. Various known methods can be employed for the condensation reaction.
- hydroxy group-containing compound examples include compounds shown below.
- Dihydroxybenzophenones such as 2,4-dihydroxybenzophenone; trihydroxybenzophenones such as 2,3,4-trihydroxybenzophenone and 2,4,6-trihydroxybenzophenone; 2,4,2′,4′-tetrahydroxybenzophenone, 2,3,4,3′-tetrahydroxybenzophenone, 2,3,4,4′-tetrahydroxybenzophenone, 2,3,4,2′-tetra Tetrahydroxybenzophenones such as hydroxy-4'-methylbenzophenone and 2,3,4,4'-tetrahydroxy-3'-methoxybenzophenone; pentahydroxybenzophenones such as 2,3,4,2′,4′-pentahydroxybenzophenone and 2,3,4,2′,6′-pentahydroxybenzophenone; Hexahydroxybenzophenones such as 2,4,6,3′,4′,5′-hexahydroxybenzophenone and 3,4,5,3′,4′,5′-
- 2,3,4,4'-tetrahydroxybenzophenone, 1,1,1-tris(p-hydroxyphenyl)ethane, and 4,4'-[1-[4-[1-[ 4-Hydroxyphenyl]-1-methylethyl]phenyl]ethylidene]bisphenol is preferred.
- 1,2-naphthoquinonediazide sulfonic acid halide 1,2-naphthoquinone diazide sulfonic acid chloride is preferable, and 1,2-naphthoquinone-2-diazide-4-sulfonic acid chloride and 1,2-naphthoquinone-2-diazide are used.
- -5-sulfonic acid chloride is more preferred, and 1,2-naphthoquinone-2-diazide-5-sulfonic acid chloride is even more preferred.
- the compounds of component (B) may be used singly or in combination of two or more.
- the content of component (B) in the positive photosensitive resin composition of the present invention is 5 parts by mass to 100 parts by mass, preferably 10 parts by mass to 60 parts by mass, with respect to 100 parts by mass of component (A). It is preferably 15 to 40 parts by mass.
- the component (C) contained in the positive-type photosensitive resin composition of the present invention is not particularly limited as long as it is a compound capable of generating an acid having an acid dissociation constant pKa of 4 or less upon exposure. Ionic photoacid generators can be mentioned.
- ADEKA Arkles registered trademark
- SP-056, SP-171 manufactured by ADEKA Co., Ltd.
- CPI registered trademark
- -100P -101A, -110A, - 110B, -110P, -200K, -210S, -300, -310B, -310FG, -400, -410B, -410S, VC-1FG, ES-1B (above, Sun-Apro ( Co., Ltd.), TPS-TF, TPS-CS, TPS-PFBS (manufactured by Toyo Gosei Co., Ltd.), TPS-102, TPS-103, TPS-105, TPS-106, TPS-109, TPS- 200, TPS-300, TPS-1000, HDS-109, MDS-103, MDS-105, MDS-109, M
- nonionic photoacid generator for example, the products and compounds shown below can be used.
- ADEKA Arkles registered trademark
- SP-082, SP-606 manufactured by ADEKA Corporation
- NA-CS1, NP-TM2, NP-SE10 manufactured by San-Apro Co., Ltd.
- SI-105, SI-106, PI-106 NDI-101, NDI-105, NDI-106, NDI-109, NDI-1001, NDI-1004, NAI-100, NAI-101, NAI-105, NAI-106, NAI- N-sulfonyloxyimides such as 109, NAI-1002, NAI-1003, and NAI-1004 (manufactured by Midori Chemical Co., Ltd.);
- IRGACURE registered trademark
- PAG103, PAG121, PAG203 manufactured by BASF Japan Co., Ltd.
- nonionic photoacid generators are preferable, N-sulfonyloxyimides are more preferable, and the formula ( Compounds represented by 6) are more preferred.
- Specific examples of the compound represented by the formula (6) include compounds represented by the following formulas (6-1) to (6-28).
- the compounds of component (C) may be used singly or in combination of two or more.
- the content of component (C) in the positive photosensitive resin composition of the present invention is 0.1 to 10 parts by mass, preferably 0.5 to 5 parts by mass, per 100 parts by mass of component (A). part by mass.
- Component (D) which is included as an optional component in the positive photosensitive resin composition of the present invention, is not particularly limited as long as it is a compound having at least two epoxy rings in the molecule. can be used.
- EPICLON registered trademark
- the compounds of component (D) may be used singly or in combination of two or more.
- the content of component (D) is 5 parts by mass to 100 parts by mass, preferably 10 parts by mass, per 100 parts by mass of component (A). parts by mass to 50 parts by mass.
- component (D) Chemical resistance can be improved by making content of a component into the said range.
- Component (E) component which is included as an optional component in the positive photosensitive resin composition of the present invention, is not particularly limited as long as it is a substance capable of transferring the energy of irradiated light to other substances. tolquinone, 1-phenyl-1,2-propanedione, phenanthrene, anthracene, 9,10-diethoxyanthracene, 9,10-dipropyloxyanthracene, 9,10-dibutoxyanthracene, 9,10-dioctanoyloxy Anthracene, 3,7-dimethoxyanthracene, pyrene, perylene, xanthone, thioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2-isopropylthioxanthone, and the like.
- the compound of the component may be used individually by 1 type, or may be used in combination of 2 or more type.
- the content of component (E) is preferably 0.01 to 5 parts by mass, per 100 parts by mass of component (A). is 0.05 to 3 parts by mass, more preferably 0.1 to 1 part by mass.
- the solvent contained in the positive photosensitive resin composition of the present invention is not particularly limited as long as it dissolves the components (A) to (C) and optional components added as necessary. All organic solvents such as hydrocarbons, halogenated hydrocarbons, ethers, alcohols, aldehydes, ketones, esters, amides, and nitriles can be used.
- hydrocarbons examples include n-pentane, cyclopentane, methylcyclopentane, n-hexane, isohexane, cyclohexane, methylcyclohexane, ethylcyclohexane, n-heptane, benzene, toluene, o-xylene, m-xylene, Examples include p-xylene and mesitylene.
- halogenated hydrocarbons examples include dichloromethane, chloroform, carbon tetrachloride, chloroethane, dichloroethane, trichloroethane, tetrachloroethane, hexachloroethane, dichloroethylene, trichloroethylene, tetrachloroethylene, chlorobenzene, hydrofluorocarbons and perfluorocarbons.
- ethers examples include diethyl ether, di-n-propyl ether, diisopropyl ether, di-n-butyl ether, diisobutyl ether, di-tert-butyl ether, di-n-pentyl ether, diisopentyl ether, di- n-hexyl ether, methyl-n-propyl ether, methyl isopropyl ether, ethyl-n-propyl ether, ethyl isopropyl ether, n-butyl methyl ether, isobutyl methyl ether, tert-butyl methyl ether, n-butyl ethyl ether, isobutyl ethyl ether, tert-butyl ethyl ether, methyl-n-pentyl ether, cyclopentyl methyl ether, n-hexyl methyl ether, cycl
- Examples of the alcohols include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, tert-butyl alcohol, 1-pentanol, 2-pentanol.
- aldehydes examples include ethanal, propanal, 2-methyl-1-propanal, butanal, 3-methylbutanal, pentanal and benzaldehyde.
- ketones examples include acetone, 2-butanone, 2-pentanone, 3-pentanone, cyclopentanone, 2,4-pentanedione, 4-methyl-2-pentanone, 4-hydroxy-4-methyl-2 -pentanone, cyclohexanone and 2-heptanone.
- esters examples include methyl formate, ethyl formate, n-propyl formate, isopropyl formate, n-butyl formate, isobutyl formate, tert-butyl formate, n-pentyl formate, isopentyl Formate, methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, tert-butyl acetate, n-pentyl acetate, isopentyl acetate, cyclopentyl acetate tart, n-hexyl acetate, isohexyl acetate, cyclohexyl acetate, n-heptyl acetate, isoheptyl acetate, n-octyl acetate, isooctyl acetate, benzy
- amides examples include N,N-dimethylformamide, N,N-dimethylacetamide, N,N-dimethylisobutyramide, N-methylpyrrolidone and N-ethylpyrrolidone.
- nitriles examples include acetonitrile, propionitrile and butyronitrile.
- solvents may be used singly or in combination of two or more.
- propylene glycol monomethyl ether propylene glycol monomethyl ether acetate
- Propylene glycol monoethyl ether propylene glycol monopropyl ether
- 2-heptanone ethyl lactate
- n-butyl lactate cyclopentanone and cyclohexanone
- the positive photosensitive resin composition of the present invention may optionally contain a surfactant for the purpose of improving coatability.
- surfactants include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether and polyoxyethylene
- Polyoxyethylene alkylaryl ethers such as nonylphenyl ether, polyoxyethylene/polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, and sorbitan trioleate
- Sorbitan fatty acid esters such as stearates, polyoxyethylene sorbitan monolaurate, polyoxyethylene sorbitan monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene
- Ftergent series (manufactured by Neos Co., Ltd.) and other fluorine-based surfactants, and Organosiloxane polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.) can be mentioned. These surfactants may be used singly or in combination of two or more.
- the content of the surfactant is 0.00 per 100 parts by mass of the total solid content excluding the solvent in the positive photosensitive resin composition. 001 to 3 parts by mass, preferably 0.005 to 1 part by mass, more preferably 0.01 to 0.5 parts by mass.
- the positive photosensitive resin composition of the present invention may further contain additives such as curing aids, antioxidants, ultraviolet absorbers, plasticizers, adhesion aids, etc. as necessary, as long as the effects of the present invention are not impaired. can contain.
- the method for preparing the positive photosensitive resin composition of the present invention is not particularly limited, but examples thereof include a method of dissolving components (A) to (C) and optionally other components in a solvent to form a uniform solution. be done. Moreover, if necessary, the solution may be filtered using a filter with a pore size of 0.1 ⁇ m to 10 ⁇ m.
- a substrate for example, a semiconductor substrate, a glass substrate, a quartz substrate, a plastic substrate, a silicon wafer, and a substrate having elements such as various metal films or color filters formed thereon
- the positive photosensitive resin composition of the present invention is applied by a coating method, and preferably prebaked using a heating means such as an oven or a hot plate to remove the solvent to form a resin film.
- Pre-baking conditions are appropriately selected from the ranges of baking temperature of 60° C. to 130° C. and baking time of 20 seconds to 30 minutes.
- the film thickness of the resin film to be formed is 0.1 ⁇ m to 10 ⁇ m, preferably 0.2 ⁇ m to 5 ⁇ m.
- a predetermined mask For example, g-line, i-line, KrF excimer laser, and ArF excimer laser can be used as light for exposure.
- the exposure dose is appropriately selected from the range of 20 mJ/cm 2 to 2000 mJ/cm 2 .
- the developing method is not particularly limited, but includes, for example, a dipping method, a puddle method and a spraying method.
- the development conditions are appropriately selected from the ranges of development temperature of 5° C. to 50° C. and development time of 10 seconds to 300 seconds.
- the developer to be used is not particularly limited as long as it can remove the exposed areas, but examples include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, sodium phosphate, potassium phosphate, and ammonia.
- TMAH tetramethylammonium hydroxide
- TEAH tetraethylammonium hydroxide
- a rinse solution may be used to wash away the developer. After development or rinsing, it can be dried by spinning in a spinnable device such as a spinner or coater, or by blowing compressed air or compressed nitrogen to remove residual developer or rinse.
- a reflow process may be included in which the pattern formed after the development process is heated using heating means such as an oven or a hot plate before the second exposure process described later.
- the reflow conditions are appropriately selected from the ranges of baking temperature of 80° C. to 130° C. and baking time of 1 minute to 90 minutes. Even if the reflow process is omitted, the spherical or hemispherical microlens can be produced. However, by including the reflow process, the spherical or hemispherical microlens can be produced at a lower temperature. It becomes possible.
- ⁇ Second exposure step> After the developing step or after the reflow step, the pattern is further exposed.
- g-line, i-line, KrF excimer laser, and ArF excimer laser can be used as light for exposure.
- the exposure amount is appropriately selected from the range of 100 mJ/cm 2 to 5000 mJ/cm 2 .
- Post-baking process> After the second exposure step, the pattern is heated using heating means such as an oven or a hot plate. Post-baking conditions are appropriately selected from the ranges of baking temperature of 80° C. to 130° C. and baking time of 1 minute to 90 minutes.
- the apparatus and conditions used for measuring the polystyrene-equivalent weight-average molecular weight MW of the copolymer are as follows. Apparatus: GPC system manufactured by JASCO Corporation Column: Shodex (registered trademark) KF-804L and KF-803L Column oven: 40°C Flow rate: 1 mL/min Eluent: Tetrahydrofuran Sample concentration: 10 mg/mL Sample injection volume: 20 ⁇ L Reference material: Monodisperse polystyrene Detector: Differential refractometer
- a solution obtained by mixing 4.5 g of 2′-azobisisobutyronitrile and 194 g of propylene glycol monomethyl ether as a solvent was placed in a dropping funnel, connected to the flask, and purged with nitrogen. Dripped. After the completion of dropping, reaction was continued for 15 hours to obtain a copolymer solution (solid content concentration: 30% by mass).
- the polystyrene-equivalent weight-average molecular weight MW of the obtained copolymer was 8,000.
- the copolymer obtained in Synthesis Example 1 is referred to as A-1 in this specification.
- Example 1 70.0 g of copolymer A-1 obtained in Synthesis Example 1 as component (A) (21.0 g as solid content), 4.8 g of B-1 as component (B), C as component (C) 0.2 g of D-1, 6.3 g of D-1 as component (D), 0.01 g of R-40 as a surfactant, 6.6 g of propylene glycol monomethyl ether as a solvent, and propylene glycol monomethyl ether acetate. 23.8 g was blended to form a uniform solution. Then, it was filtered using a polyethylene microfilter with a pore size of 0.10 ⁇ m to obtain a positive photosensitive resin composition (solid concentration: 29% by mass).
- Example 2 70.0 g of copolymer A-1 obtained in Synthesis Example 1 as component (A) (21.0 g as solid content), 4.8 g of B-1 as component (B), C as component (C) 0.3 g of D-2, 6.3 g of D-1 as component (D), 0.01 g of R-40 as a surfactant, 6.8 g of propylene glycol monomethyl ether as a solvent, and propylene glycol monomethyl ether acetate. 23.9 g was blended to form a uniform solution. Then, it was filtered using a polyethylene microfilter with a pore size of 0.10 ⁇ m to obtain a positive photosensitive resin composition (solid concentration: 29% by mass).
- Example 3 70.0 g of copolymer A-2 obtained in Synthesis Example 2 as component (A) (21.0 g as solid content), 4.8 g of B-1 as component (B), C as component (C) 0.2 g of D-1, 6.3 g of D-1 as component (D), 0.01 g of R-40 as a surfactant, 6.6 g of propylene glycol monomethyl ether as a solvent, and propylene glycol monomethyl ether acetate 23.8 g of was blended to form a uniform solution. Then, it was filtered using a polyethylene microfilter with a pore size of 0.10 ⁇ m to obtain a positive photosensitive resin composition (solid concentration: 29% by mass).
- Example 4 70.0 g of copolymer A-3 obtained in Synthesis Example 3 as component (A) (21.0 g as solid content), 4.8 g of B-1 as component (B), C as component (C) 0.2 g of D-1, 6.3 g of D-1 as component (D), 0.01 g of R-40 as a surfactant, 30.2 g of propylene glycol monomethyl ether as a solvent, and propylene glycol monomethyl ether acetate. 79.2 g was blended to form a uniform solution. Then, it was filtered using a polyethylene microfilter with a pore size of 0.10 ⁇ m to obtain a positive photosensitive resin composition (solid concentration: 17% by mass).
- Example 5 70.0 g of copolymer A-3 obtained in Synthesis Example 3 as component (A) (21.0 g as solid content), 4.8 g of B-1 as component (B), C as component (C) 0.2 g of R-1, 0.01 g of R-40 as a surfactant, 25.1 g of propylene glycol monomethyl ether and 74.1 g of propylene glycol monomethyl ether acetate as solvents were blended to form a uniform solution. Then, it was filtered using a polyethylene microfilter with a pore size of 0.10 ⁇ m to obtain a positive photosensitive resin composition (solid content concentration: 15% by mass).
- Table 1 shows the contents of each component contained in the positive photosensitive resin compositions of Examples 1 to 6 and the contents of components (B) to (E) with respect to 100 parts by mass of component (A).
- a mask for forming a square dot pattern of 4 ⁇ m ⁇ 4 ⁇ m/a space of 4 ⁇ m was used for the resin film having a film thickness of 4 ⁇ m (Examples 1 to 3 and Comparative Examples 1 and 2).
- a mask for forming a 1 ⁇ m ⁇ 1 ⁇ m square dot pattern/1 ⁇ m space was used for the 1 ⁇ m-thick resin film (Examples 4 to 6).
- TMAH tetramethylammonium hydroxide
- the entire surface of the square dot pattern is subjected to a second exposure at 500 mJ/cm 2 , and then baked on a hot plate at the post-bake temperature shown in Table 2 for 10 minutes.
- a microlens was produced.
- the entire surface of the 1 ⁇ m ⁇ 1 ⁇ m square dot pattern formed using the positive photosensitive resin composition prepared in Example 4 was not baked at the reflow temperature (in Table 2, the reflow temperature is indicated as “no”). display), using the i-line stepper, performing a second exposure at 500 mJ/cm 2 , followed by baking on a hot plate at the post-baking temperature shown in Table 2 for 10 minutes to fabricate a microlens.
- the shape of the fabricated microlens was evaluated as " ⁇ " when it was a quadrangular prism or truncated quadrangular pyramid, and as " ⁇ ” when it was spherical or hemispherical. Table 2 shows the evaluation results.
- the silicon wafer on which the cured film was formed was immersed in propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, cyclohexanone, and a 2.38 mass% concentration tetramethylammonium hydroxide (TMAH) aqueous solution at 23°C for 5 minutes. bottom.
- TMAH tetramethylammonium hydroxide
- the film thickness of the cured film was measured before and after immersion, and the change in film thickness before and after immersion was calculated. If even one of the solvents used for immersion has a film thickness change of 10% or more compared to the film thickness before immersion, the chemical resistance is "x", and the film thickness change is less than 10% for all solvents. In that case, the chemical resistance was evaluated as “ ⁇ ”. Table 2 shows the evaluation results.
- ⁇ THS test> Using the positive photosensitive resin compositions prepared in Examples 1 to 6, a cured film was formed on a quartz substrate according to the procedure described in [Evaluation of Transparency].
- the quartz substrate on which the cured film was formed was stored for 1,000 hours in a constant temperature and humidity chamber whose interior was kept at 85 ° C. and a relative humidity of 85%. Transmittance was measured. When the transmittance increased or decreased by 5% or more with respect to the transmittance at a wavelength of 400 nm before storage for 1,000 hours, it was evaluated as "x", and when the transmittance increased or decreased by less than 5%, it was evaluated as "good”. Table 2 shows the evaluation results.
- ⁇ Xenon arc test> Using the positive photosensitive resin compositions prepared in Examples 1 to 6, a cured film was formed on a quartz substrate according to the procedure described in [Evaluation of Transparency]. A cut filter (L38, manufactured by Shibuya Optical Co., Ltd.) is attached to the quartz substrate on which the cured film is formed, and the xenon arc tester (Q-SUNXe-1, manufactured by Q-Lab) is subjected to 25 million [lx h ] After exposure, the transmittance at a wavelength of 400 nm was measured using the UV-visible spectrophotometer.
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Abstract
Description
(A)成分:(a1)下記式(1)で表されるモノマー、(a2)エポキシ環を含有するモノマー、及び(a3)酸解離定数pKaが14以上であるヒドロキシ基を含有するモノマーの共重合体であって、カルボキシ基及びカルボン酸無水物基を含まない共重合体
(B)成分:キノンジアジド化合物
(C)成分:光酸発生剤
(式中、R0は水素原子又はメチル基を表し、R1は単結合又は炭素原子数1又は2のアルキレン基を表し、R2はメチル基を表し、aは1又は2を表し、bは0乃至2の整数を表す。)
(式中、R0は水素原子又はメチル基を表し、R3は下記式(I)で表される2価の有機基を表し、R4は下記式(4)又は下記式(5)で表される1価の有機基を表し、R5は下記式(I´)で表される1価の有機基を表す。)
(式中、cは0乃至3の整数を表し、dは1乃至3の整数を表し、eはそれぞれ独立に2乃至6の整数を表し、*は前記式(2)又は前記式(3)で表されるモノマーのアルケニル基との結合手を表し、・は前記式(4)又は前記式(5)で表される1価の有機基との結合手を表す。)
(式中、R0はそれぞれ独立に水素原子又はメチル基を表し、R1は単結合又は炭素原子数1又は2のアルキレン基を表し、R2はメチル基を表し、bは0乃至2の整数を表し、R4は下記式(4)又は下記式(5)で表される1価の有機基を表し、eは2乃至6の整数を表す。)
(式中、R6は炭素原子数1乃至10の炭化水素基又はパーフルオロアルキル基を表し、R7は炭素原子数1乃至8の直鎖状のアルキル基もしくはアルコキシ基、又は炭素原子数3乃至8の分岐鎖状のアルキル基もしくはアルコキシ基を表す。)
(D)成分:多官能エポキシ化合物
(E)成分:増感剤
[(A)成分]
本発明のポジ型感光性樹脂組成物に含まれる(A)成分は、(a1)下記式(1)で表されるモノマー、(a2)エポキシ環を含有するモノマー、及び(a3)酸解離定数pKaが14以上であるヒドロキシ基を含有するモノマーの共重合体であって、カルボキシ基及びカルボン酸無水物基を含まない共重合体である。ここで、カルボン酸無水物基は、-CO-O-CO-で表される2価の基である。
(式中、R0は水素原子又はメチル基を表し、R1は単結合又は炭素原子数1又は2のアルキレン基を表し、R2はメチル基を表し、aは1又は2を表し、bは0乃至2の整数を表す。)
これらのモノマーは1種単独で使用しても、2種以上を組み合わせて使用してもよい。
これらのモノマーは1種単独で使用しても、2種以上を組み合わせて使用してもよい。
本発明のポジ型感光性樹脂組成物に含まれる(B)成分は、1,2-キノンジアジド基を有する化合物であれば特に限定されず、例えば、ヒドロキシ基含有化合物と、1,2-ナフトキノンジアジドスルホン酸ハライドとの縮合物を用いることできる。具体的には、前記ヒドロキシ基含有化合物のヒドロキシ基のうち、10モル%乃至100モル%、好ましくは20モル%乃至95モル%が、前記1,2-ナフトキノンジアジドスルホン酸ハライドでエステル化された化合物を用いることができる。前記縮合反応は、各種公知の方法を採用することができる。
2,4-ジヒドロキシベンゾフェノン等のジヒドロキシベンゾフェノン類;
2,3,4-トリヒドロキシベンゾフェノン及び2,4,6-トリヒドロキシベンゾフェノン等のトリヒドロキシベンゾフェノン類;
2,4,2’,4’-テトラヒドロキシベンゾフェノン、2,3,4,3’-テトラヒドロキシベンゾフェノン、2,3,4,4’-テトラヒドロキシベンゾフェノン、2,3,4,2’-テトラヒドロキシ-4’-メチルベンゾフェノン、及び2,3,4,4’-テトラヒドロキシ-3’-メトキシベンゾフェノン等のテトラヒドロキシベンゾフェノン類;
2,3,4,2’,4’-ペンタヒドロキシベンゾフェノン及び2,3,4,2’,6’-ペンタヒドロキシベンゾフェノン等のペンタヒドロキシベンゾフェノン類;
2,4,6,3’,4’,5’-ヘキサヒドロキシベンゾフェノン及び3,4,5,3’,4’,5’-ヘキサヒドロキシベンゾフェノン等のヘキサヒドロキシベンゾフェノン類;
2,2-ビス(4-ヒドロキシフェニル)プロパン、1,1-ビス(4-ヒドロキシフェニル)シクロヘキサン、1,3,3-トリス(4-ヒドロキシフェニル)ブタン、ビス(2,4-ジヒドロキシフェニル)メタン、ビス(p-ヒドロキシフェニル)メタン、トリス(p-ヒドロキシフェニル)メタン、1,1,1-トリス(p-ヒドロキシフェニル)エタン、ビス(2,3,4-トリヒドロキシフェニル)メタン、2,2-ビス(2,3,4-トリヒドロキシフェニル)プロパン、1,1,3-トリス(2,5-ジメチル-4-ヒドロキシフェニル)-3-フェニルプロパン、4,4’-[1-[4-[1-[4-ヒドロキシフェニル]-1-メチルエチル]フェニル]エチリデン]ビスフェノール、ビス(2,5-ジメチル-4-ヒドロキシフェニル)-2-ヒドロキシフェニルメタン、3,3,3’,3’-テトラメチル-1,1’-スピロビインデン-5,6,7,5’,6’,7’-ヘキサノール、及び2,2,4-トリメチル-7,2’,4’-トリヒドロキシフラバン等の(ポリヒドロキシフェニル)アルカン類;
フェノール、o-クレゾール、m-クレゾール、p-クレゾール、ハイドロキノン、レゾルシノール、カテコール、ガリック酸メチル、ガリック酸エチル、2-メチル-2-(2,4-ジヒドロキシフェニル)-4-(4-ヒドロキシフェニル)-7-ヒドロキシクロマン、1-[1-(3-{1-(4-ヒドロキシフェニル)-1-メチルエチル}-4,6-ジヒドロキシフェニル)-1-メチルエチル]-3-(1-(3-{1-(4-ヒドロキシフェニル)-1-メチルエチル}-4,6-ジヒドロキシフェニル)-1-メチルエチル)ベンゼン、及び4,6-ビス{1-(4-ヒドロキシフェニル)-1-メチルエチル}-1,3-ジヒドロキシベンゼン等のその他化合物。
これらの化合物の中でも、2,3,4,4’-テトラヒドロキシベンゾフェノン、1,1,1-トリス(p-ヒドロキシフェニル)エタン、及び4,4’-[1-[4-[1-[4-ヒドロキシフェニル]-1-メチルエチル]フェニル]エチリデン]ビスフェノールが好ましい。
本発明のポジ型感光性樹脂組成物に含まれる(C)成分は、露光により酸解離定数pKaが4以下の酸を生じ得る化合物であれば特に限定されず、イオン性光酸発生剤及び非イオン性光酸発生剤が挙げられる。
アデカアークルズ(登録商標)SP-056、同SP-171(以上、(株)ADEKA製)、CPI(登録商標)-100B(40)、同-100P、同-101A、同-110A、同-110B、同-110P、同-200K、同-210S、同-300、同-310B、同-310FG、同-400、同-410B、同-410S、VC-1FG、ES-1B(以上、サンアプロ(株)製)、TPS-TF、TPS-CS、TPS-PFBS(以上、東洋合成工業(株)製)、TPS-102、TPS-103、TPS-105、TPS-106、TPS-109、TPS-200、TPS-300、TPS-1000、HDS-109、MDS-103、MDS-105、MDS-109、MDS-205、MDS-209、BDS-109、MNPS-109、DTS-102、DTS-103、DTS-105、DTS-200、NDS-103、NDS-105、NDS-155、及びNDS-165(以上、みどり化学(株)製)等のアリールスルホニウム塩類;
アデカアークルズ(登録商標)SP-140(以上、(株)ADEKA製)、IK-1、IK-1PC(80)、IK-1FG、(以上、サンアプロ(株)製)、DTBPI-PFBS(以上、東洋合成工業(株)製)、DPI-105、DPI-106、DPI-109、DPI-201、BI-105、MPI-105、MPI-106、MPI-109、BBI-102、BBI-103、BBI-105、BBI-106、BBI-109、BBI-110、BBI-200、BBI-201、BBI-300、及びBBI-301(以上、みどり化学(株)製)等のアリールヨードニウム塩類。
アデカアークルズ(登録商標)SP-082、同SP-606(以上、(株)ADEKA製)、NA-CS1、NP-TM2、NP-SE10(以上、サンアプロ(株)製)、SI-105、SI-106、PI-106、NDI-101、NDI-105、NDI-106、NDI-109、NDI-1001、NDI-1004、NAI-100、NAI-101、NAI-105、NAI-106、NAI-109、NAI-1002、NAI-1003、及びNAI-1004(以上、みどり化学(株)製)等のN-スルホニルオキシイミド類;
IRGACURE(登録商標)PAG103、同PAG121、同PAG203(以上、BASFジャパン(株)製)、PAI-01、PAI-101、PAI-106、PAI-1001、PAI-1002、PAI-1003、及びPAI-1004(以上、みどり化学(株)製)等のオキシムスルホネート類;
TAZ-100、TAZ-101、TAZ-102、TAZ-103、TAZ-104、TAZ-107、TAZ-108、TAZ-109、TAZ-110、TAZ-113、TAZ-114、TAZ-118、TAZ-122、TAZ-123、TAZ-203、及びTAZ-204(以上、みどり化学(株)製)等のトリアジン類。
本発明のポジ型感光性樹脂組成物に任意成分として含まれる(D)成分は、エポキシ環を分子中に少なくとも2つ有する化合物であれば特に限定されず、例えば、以下に示す商品及び化合物を用いることができる。
EPICLON(登録商標)830、同830-S、同835、同840、同840-S、同850、同850-S、同850-LC、同HP-820(以上、DIC(株)製)、DENACOL(登録商標)EX-201、同EX-211、同EX-212、同EX-252、同EX-810、同EX-811、同EX-821、同EX-830、同EX-832、同EX-841、同EX-850、同EX-851、同EX-861、同EX-920、同EX-931、同EX-991L、同EX-313、同EX-314、同EX-321、同EX-321L、同EX-411、同EX-421、同EX-512、同EX-521、同EX-612、同EX-614、同EX-614B、同EX-622(以上、ナガセケムテックス(株)製)、jER(登録商標)152、同630、同825、同827、同828、同828EL、同828US、同828XA(以上、三菱ケミカル(株)製)、TETRAD(登録商標)-C、同-X(以上、三菱ガス化学(株)製)、セロキサイド(登録商標)2021P、同2081、エポリード(登録商標)GT401(以上、(株)ダイセル製)、エポトート(登録商標)YD-115、同YD-115CA、同YD-127、同YD-128、同YD-128G、同YD-128S、同YD-128CA、同YD-8125、同YD-825GS、同YDF-170、同YDF-170N、同YDF-8170C、同YDF-870GS、同ZX-1059、同YH-404、同YH-434、同YH-434L、同YH-513、同YH-523、同ST-3000(以上、日鉄ケミカル&マテリアル(株)製)、アデカレジン(登録商標)EP-4100、同EP-4100G、同EP-4100E、同EP-4100TX、同EP-4300E、同EP-4100、同EP-4400、同EP-4520S、同EP-4530、同EP-4901、同EP-4901E、同EP-4000、同EP-4005、同EP-7001、同EP-4080E、同EPU-6、同EPU-7N、同EPU-11F、同EPU-15F、同EPU-1395、同EPU-73B、同EPU-17、同EPU-17T-6、同EPR-1415-1、同EPR-2000、同EPR-2007、アデカグリシロール(登録商標)ED-503、同ED-503G、同ED-506、同ED-523T、同ED-505(以上、(株)ADEKA製)、スミエポキシ(登録商標)ELM-434、同ELM-434L、同ELM-434VL、同ELM-100、同ELM-100H(以上、住友化学(株)製)、エポライトM-1230、同40E,同100E、同200E、同400E、同70P、同200P、同400P、同1500NP、同1600、同80MF、同4000、同3002(N)(以上、共栄社化学(株)製)及びTHI-DE(ENEOS(株)製)等の多官能エポキシ樹脂。
本発明のポジ型感光性樹脂組成物に任意成分として含まれる(E)成分は、照射された光のエネルギーを他の物質に渡すことができる物質であれば特に限定されず、例えば、p-トルキノン、1-フェニル-1,2-プロパンジオン、フェナントレン、アントラセン、9,10-ジエトキシアントラセン、9,10-ジプロピルオキシアントラセン、9,10-ジブトキシアントラセン、9,10-ジオクタノイルオキシアントラセン、3,7-ジメトキシアントラセン、ピレン、ペリレン、キサントン、チオキサントン、2,4-ジメチルチオキサントン、2,4-ジエチルチオキサントン、及び2-イソプロピルチオキサントン等が挙げられる。
本発明のポジ型感光性樹脂組成物に含まれる溶剤は、(A)成分乃至(C)成分、並びに必要に応じて添加される任意成分を溶解するものであれば特に限定されず、例えば、炭化水素類、ハロゲン化炭化水素類、エーテル類、アルコール類、アルデヒド類、ケトン類、エステル類、アミド類、及びニトリル類等の全ての有機溶媒を使用することができる。
本発明のポジ型感光性樹脂組成物は、塗布性を向上させる目的で、任意で界面活性剤を含有することもできる。界面活性剤としては、例えば、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンセチルエーテル、ポリオキシエチレンオレイルエーテル等のポリオキシエチレンアルキルエーテル類、ポリオキシエチレンオクチルフェニルエーテル及びポリオキシエチレンノニルフェニルエーテル等のポリオキシエチレンアルキルアリールエーテル類、ポリオキシエチレン/ポリオキシプロピレンブロックコポリマー類、ソルビタンモノラウレート、ソルビタンモノパルミテート、ソルビタンモノステアレート、ソルビタンモノオレート、ソルビタントリオレート、及びソルビタントリステアレート等のソルビタン脂肪酸エステル類、ポリオキシエチレンソルビタンモノラウレート、ポリオキシエチレンソルビタンモノパルミテート、ポリオキシエチレンソルビタンモノステアレート、ポリオキシエチレンソルビタントリオレート、及びポリオキシエチレンソルビタントリステアレート等のポリオキシエチレンソルビタン脂肪酸エステル類等のノニオン系界面活性剤、エフトップ(登録商標)EF301、同EF303、同EF352(以上、三菱マテリアル電子化成(株)製)、メガファック(登録商標)F-171、同F-173、同R-30、同R-40、同R-40-LM(以上、DIC(株)製)、フロラードFC430、同FC431(以上、住友スリーエム(株)製)、アサヒガード(登録商標)AG710、サーフロン(登録商標)S-382、同SC101、同SC102、同SC103、同SC104、同SC105、同SC106(AGC(株)製)、FTX-206D、FTX-212D、FTX-218、FTX-220D、FTX-230D、FTX-240D、FTX-212P、FTX-220P、FTX-228P、FTX-240G等のフタージェントシリーズ((株)ネオス製)等のフッ素系界面活性剤、及びオルガノシロキサンポリマーKP341(信越化学工業(株)製)を挙げることができる。これらの界面活性剤は1種単独で使用しても、2種以上を組み合わせて使用してもよい。
本発明のポジ型感光性樹脂組成物の調製方法は特に限定されないが、例えば、(A)成分乃至(C)成分及び任意でその他の成分を溶剤に溶解し、均一な溶液とする方法が挙げられる。また、必要に応じて、該溶液を孔径0.1μm乃至10μmのフィルターを用いてろ過してもよい。
本発明のポジ型感光性樹脂組成物を用いたマイクロレンズの作製例について説明する。
<塗布工程>
基材(例えば、半導体基板、ガラス基板、石英基板、プラスチック基板、シリコンウエハー、及びこれらの表面に各種金属膜又はカラーフィルター等の素子が形成された基板)上に、スピナー又はコーター等の適当な塗布方法により本発明のポジ型感光性樹脂組成物を塗布し、好ましくはその後、オーブン又はホットプレート等の加熱手段を用いてプリベークを行って溶剤を除去することにより樹脂膜を形成する。プリベーク条件は、ベーク温度60℃乃至130℃、ベーク時間20秒間乃至30分間の範囲から適宜選択される。形成される樹脂膜の膜厚としては、0.1μm乃至10μm、好ましくは0.2μm乃至5μmである。
前記塗布工程の後、形成された樹脂膜の少なくとも一部に、所定のマスクを介して露光する。露光する光線としては、例えば、g線、i線、KrFエキシマレーザー及びArFエキシマレーザーを使用することができる。露光量は、20mJ/cm2乃至2000mJ/cm2の範囲から適宜選択される。
前記第一露光工程の後、樹脂膜の露光部を現像液により除去し、該樹脂膜の未露光部のパターンを形成する。現像方法は特に限定されないが、例えば、ディップ法、パドル法及びスプレー法が挙げられる。現像条件は、現像温度5℃乃至50℃、現像時間10秒乃至300秒の範囲から適宜選択される。使用する現像液としては、露光部を除去することができる限り特に限定されないが、例えば、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸水素ナトリウム、炭酸カリウム、リン酸ナトリウム、リン酸カリウム、アンモニア、テトラメチルアンモニウムヒドロキシド(TMAH)、及びテトラエチルアンモニウムヒドロキシド(TEAH)等のアルカリ水溶液が挙げられる。また、アルカリ水溶液に界面活性剤や有機溶媒を適当量添加したものを現像液として使用してもよい。これらの現像液は1種単独で、又は2種以上を組み合わせて使用してもよい。
前記現像工程の後に形成されたパターンを、後述する第二露光工程の前に、オーブン又はホットプレート等の加熱手段を用いて加熱するリフロー工程を含んでもよい。リフロー条件は、ベーク温度80℃乃至130℃、ベーク時間1分間乃至90分間の範囲から適宜選択される。なお、リフロー工程を省略しても球欠形状又は半球形状のマイクロレンズを作製することはできるが、リフロー工程を含むことによって、より低温で球欠形状又は半球形状のマイクロレンズを作製することが可能となる。
前記現像工程の後、又は前記リフロー工程の後、前記パターンをさらに露光する。露光する光線としては、例えば、g線、i線、KrFエキシマレーザー及びArFエキシマレーザーを使用することができる。露光量は、100mJ/cm2乃至5000mJ/cm2の範囲から適宜選択される。
前記第二露光工程の後、前記パターンをオーブン又はホットプレート等の加熱手段を用いて加熱する。ポストベーク条件は、ベーク温度80℃乃至130℃、ベーク時間1分間乃至90分間の範囲から適宜選択される。
装置:日本分光(株)製GPCシステム
カラム:Shodex(登録商標)KF-804L及びKF-803L
カラムオーブン:40℃
流量:1mL/分
溶離液:テトラヒドロフラン
試料濃度:10mg/mL
試料注入量:20μL
標準物質:単分散ポリスチレン
検出器:示差屈折計
<(B)成分>
B-1:4,4’-[1-[4-[1-[4-ヒドロキシフェニル]-1-メチルエチル]フェニル]エチリデン]ビスフェノール1モルと1,2-ナフトキノン-2-ジアジド-5-スルホン酸クロリド1.5モルとの縮合物
<(C)成分>
C-1:アデカアークルズ(登録商標)SP-606((株)ADEKA製)
C-2:CPI-110P(サンアプロ(株)製)
<(D)成分>
D-1:エポリード(登録商標)GT401((株)ダイセル製)
<(E)成分>
E-1:2-イソプロピルチオキサントン(東京化成工業(株)製)
<界面活性剤>
R-40:メガファック(登録商標)R-40(DIC(株)製)
<合成例1>
フラスコ内に撹拌子と、溶剤としてプロピレングリコールモノメチルエーテル50gを入れ、加温したオイルバスに浸漬して87℃に保持した。次に、(a1)前記式(1)で表されるモノマーとしてN-(4-ヒドロキシフェニル)メタクリルアミド30g、(a2)エポキシ環を含有するモノマーとして3,4-エポキシシクロヘキシルメチルメタクリレート(前記式(2-6))60g、(a3)酸解離定数pKaが14以上であるヒドロキシ基を含有するモノマーとして2-ヒドロキシエチルメタクリレート(前記式(3-5))10g、熱ラジカル発生剤として2,2’-アゾビスイソブチロニトリル4.5g、及び溶剤としてプロピレングリコールモノメチルエーテル194gを混合した溶液を、滴下漏斗に入れて前記フラスコに接続し、窒素置換した後、撹拌しながら3時間かけて滴下した。滴下終了後、さらに15時間反応させることで共重合体の溶液(固形分濃度30質量%)を得た。得られた共重合体のポリスチレン換算重量平均分子量MWは8,000であった。以下、本明細書では、合成例1で得られた共重合体をA-1と表す。
N-(4-ヒドロキシフェニル)メタクリルアミドを25g、2-ヒドロキシエチルメタクリレートを15g、2,2’-アゾビスイソブチロニトリルを4.6g使用する以外は合成例1と同様の方法で、共重合体の溶液(固形分濃度30質量%)を得た。得られた共重合体のポリスチレン換算重量平均分子量MWは8,000であった。以下、本明細書では、合成例2で得られた共重合体をA-2と表す。
N-(4-ヒドロキシフェニル)メタクリルアミドを20g、2-ヒドロキシエチルメタクリレートを20g、2,2’-アゾビスイソブチロニトリルを4.7g使用する以外は合成例1と同様の方法で、共重合体の溶液(固形分濃度30質量%)を得た。得られた共重合体のポリスチレン換算重量平均分子量MWは8,000であった。以下、本明細書では、合成例3で得られた共重合体をA-3と表す。
フラスコ内に撹拌子と、溶剤としてプロピレングリコールモノメチルエーテル50gを入れ、加温したオイルバスに浸漬して80℃に保持した。次に、モノマーとしてN-(4-ヒドロキシフェニル)メタクリルアミド40g及び3,4-エポキシシクロヘキシルメチルメタクリレート60g、熱ラジカル発生剤として2,2’-アゾビスイソブチロニトリル4.4g、並びに溶剤としてプロピレングリコールモノメチルエーテル194gを混合した溶液を、滴下漏斗に入れて前記フラスコに接続し、窒素置換した後、撹拌しながら3時間かけて滴下した。滴下終了後、さらに15時間反応させることで共重合体の溶液(固形分濃度30質量%)を得た。得られた共重合体のポリスチレン換算重量平均分子量MWは11,000であった。以下、本明細書では、合成例4で得られた共重合体をA-4と表す。
フラスコ内に撹拌子と、溶剤としてプロピレングリコールモノメチルエーテル90gを入れ、加温したオイルバスに浸漬して70℃に保持した。次に、モノマーとしてアクリル酸10g、4-ヒドロキシブチルアクリレート30g及びスチレン60g、熱ラジカル発生剤として2,2’-アゾビスイソブチロニトリル4.5g、並びに溶剤としてプロピレングリコールモノメチルエーテル105gを混合した溶液を、滴下漏斗に入れて前記フラスコに接続し、窒素置換した後、撹拌しながら3時間かけて滴下した。滴下終了後、さらに15時間反応させることで、共重合体の溶液(固形分濃度35質量%)を得た。得られた共重合体のポリスチレン換算重量平均分子量MWは18,000であった。以下、本明細書では、合成例5で得られた共重合体をA-5と表す。
<実施例1>
(A)成分として合成例1で得られた共重合体A-1を70.0g(固形分として21.0g)、(B)成分としてB-1を4.8g、(C)成分としてC-1を0.2g、(D)成分としてD-1を6.3g、界面活性剤としてR-40を0.01g、溶剤としてプロピレングリコールモノメチルエーテルを6.6g及びプロピレングリコールモノメチルエーテルアセタートを23.8g配合し、均一溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、ポジ型感光性樹脂組成物(固形分濃度29質量%)を得た。
(A)成分として合成例1で得られた共重合体A-1を70.0g(固形分として21.0g)、(B)成分としてB-1を4.8g、(C)成分としてC-2を0.3g、(D)成分としてD-1を6.3g、界面活性剤としてR-40を0.01g、溶剤としてプロピレングリコールモノメチルエーテルを6.8g及びプロピレングリコールモノメチルエーテルアセタートを23.9g配合し、均一溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、ポジ型感光性樹脂組成物(固形分濃度29質量%)を得た。
(A)成分として合成例2で得られた共重合体A-2を70.0g(固形分として21.0g)、(B)成分としてB-1を4.8g、(C)成分としてC-1を0.2g、(D)成分としてD-1をを6.3g、界面活性剤としてR-40を0.01g、溶剤としてプロピレングリコールモノメチルエーテルを6.6g及びプロピレングリコールモノメチルエーテルアセタートを23.8g配合し、均一溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、ポジ型感光性樹脂組成物(固形分濃度29質量%)を得た。
(A)成分として合成例3で得られた共重合体A-3を70.0g(固形分として21.0g)、(B)成分としてB-1を4.8g、(C)成分としてC-1を0.2g、(D)成分としてD-1を6.3g、界面活性剤としてR-40を0.01g、溶剤としてプロピレングリコールモノメチルエーテルを30.2g及びプロピレングリコールモノメチルエーテルアセタートを79.2g配合し、均一溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、ポジ型感光性樹脂組成物(固形分濃度17質量%)を得た。
(A)成分として合成例3で得られた共重合体A-3を70.0g(固形分として21.0g)、(B)成分としてB-1を4.8g、(C)成分としてC-1を0.2g、界面活性剤としてR-40を0.01g、溶剤としてプロピレングリコールモノメチルエーテルを25.1g及びプロピレングリコールモノメチルエーテルアセタートを74.1g配合し、均一溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、ポジ型感光性樹脂組成物(固形分濃度15質量%)を得た。
(A)成分として合成例3で得られた共重合体A-3を84.0g(固形分として25.2g)、(B)成分としてB-1を5.8g、(C)成分としてC-1を0.2g、(D)成分としてD-1を7.6g、(E)成分としてE-1を0.05g、界面活性剤としてR-40を0.01g、溶剤としてプロピレングリコールモノメチルエーテルを36.2g及びプロピレングリコールモノメチルエーテルアセタートを95.0g配合し、均一溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、ポジ型感光性樹脂組成物(固形分濃度17質量%)を得た。
(A)成分に該当しない合成例4で得られた共重合体A-4を70.0g(固形分として21.0g)、(B)成分としてB-1を4.8g、(C)成分としてC-1を0.2g、(D)成分としてD-1を6.3g、界面活性剤としてR-40を0.01g、溶剤としてプロピレングリコールモノメチルエーテルを9.4g及びプロピレングリコールモノメチルエーテルアセタートを25.0g配合し、均一溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、ポジ型感光性樹脂組成物(固形分濃度28質量%)を得た。
(A)成分に該当しない合成例5で得られた共重合体A-5を60.0g(固形分として21.0g)、(B)成分としてB-1を4.8g、(C)成分としてC-1を0.2g、(D)成分としてD-1を10.5g、界面活性剤としてR-40を0.01g、溶剤としてプロピレングリコールモノメチルエーテルを3.8g及びプロピレングリコールモノメチルエーテルアセタートを35.1g配合し、均一溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、ポジ型感光性樹脂組成物(固形分濃度32質量%)を得た。
実施例1乃至実施例6並びに比較例1及び比較例2で調製したポジ型感光性樹脂組成物を、それぞれシリコンウエハー上にスピンコーターを用いて塗布し、ホットプレート上で80℃、90秒間プリベークを行い、表2に記載の膜厚を有する樹脂膜を形成した。次に、該樹脂膜に対して、i線ステッパー(NSR-2205i12D、NA=0.63、(株)ニコン製)を用い、所定のマスクを介して表2に記載の露光量で第一露光を行った。ここで、該マスクとしては、膜厚4μmの樹脂膜(実施例1乃至実施例3並びに比較例1及び比較例2)については4μm×4μmの正方形ドットパターン/4μmスペースを形成するマスクを、膜厚1μmの樹脂膜(実施例4乃至実施例6)については1μm×1μmの正方形ドットパターン/1μmスペースを形成するマスクを用いた。その後、前記第一露光から10分以内に2.38質量%濃度の水酸化テトラメチルアンモニウム(TMAH)水溶液を用いて現像を行い、膜厚4μmの樹脂膜については4μm×4μmの正方形ドットパターンを、膜厚1μmの樹脂膜については1μm×1μmの正方形ドットパターンを形成した。形成された正方形ドットパターンを、走査型電子顕微鏡を用いて5000倍の倍率にて観察し、隣り合う正方形ドットパターン間のスペース部分に、前記樹脂膜の残渣が明確に視認できる場合はパターニング性“×”、前記樹脂膜の残渣が視認できない場合はパターニング性“○”と評価した。評価結果を表2に示す。
実施例1乃至実施例6並びに比較例1及び比較例2で調製したポジ型感光性樹脂組成物を用い、前記[パターニング性評価]に記載した手順により、膜厚4μmの樹脂膜については4μm×4μmの正方形ドットパターンを、膜厚1μmの樹脂膜については1μm×1μmの正方形ドットパターンを、シリコンウエハー上に形成した。続いて、前記正方形ドットパターンに対し、ホットプレート上で表2に記載のリフロー温度にて5分間ベークを行った。さらに、前記i線ステッパーを用い、前記正方形ドットパターン全面に対して500mJ/cm2にて第二露光を行った後、ホットプレート上で表2に記載のポストベーク温度にて10分間ベークを行うことで、マイクロレンズを作製した。さらに、実施例4で調製したポジ型感光性樹脂組成物を用いて形成した1μm×1μmの正方形ドットパターン全面に対し、リフロー温度でベークを行わずに(表2においてリフロー温度を“無し”と表示)、前記i線ステッパーを用い、500mJ/cm2にて第二露光を行った後、ホットプレート上で表2に記載のポストベーク温度にて10分間ベークを行うことで、マイクロレンズを作製した。作製したマイクロレンズの形状が、四角柱又は四角錐台であるものを“□”、球欠形状又は半球形状であるものを“〇”と評価した。評価結果を表2に示す。
実施例1乃至実施例6並びに比較例1及び比較例2で調製したポジ型感光性樹脂組成物を、それぞれシリコンウエハー上にスピンコーターを用いて塗布し、ホットプレート上で80℃、90秒間プリベークを行い、表2に記載の膜厚を有する樹脂膜を形成した。次に、該樹脂膜の全面に対して、前記i線ステッパーを用いて500mJ/cm2にて露光した後、ホットプレート上で表2に記載のポストベーク温度にて10分間ベークを行うことで、硬化膜を形成した。硬化膜が形成されたシリコンウエハーを、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセタート、シクロヘキサノン及び2.38質量%濃度の水酸化テトラメチルアンモニウム(TMAH)水溶液それぞれに、23℃にて5分間浸漬した。浸漬前及び浸漬後の前記硬化膜の膜厚測定を行い、浸漬前後での膜厚変化を算出した。前記浸漬に使用した溶剤のうち、一つでも浸漬前の膜厚に対して10%以上の膜厚増減がある場合は薬品耐性“×”、全ての溶剤について膜厚増減が10%未満である場合は薬品耐性“○”と評価した。評価結果を表2に示す。
実施例1乃至実施例6並びに比較例1及び比較例2で調製したポジ型感光性樹脂組成物を、それぞれ石英基板上にスピンコーターを用いて塗布し、ホットプレート上で80℃、90秒間プリベークを行い、表2に記載の膜厚を有する樹脂膜を形成した。次に、該樹脂膜の全面に対して、前記i線ステッパーを用いて500mJ/cm2にて露光した後、ホットプレート上で表2に記載のポストベーク温度にて10分間ベークを行うことで、硬化膜を形成した。硬化膜が形成された石英基板を、紫外可視分光光度計UV-2550((株)島津製作所製)を用いて、波長400nmにおける透過率を測定した。波長400nmにおける透過率が90%未満である場合は透明性“×”、90%以上である場合は透明性“○”と評価した。評価結果を表2に示す。
<HTS試験>
実施例1乃至実施例6で調製したポジ型感光性樹脂組成物を用い、前記[透明性評価]に記載した手順により硬化膜を石英基板上に形成した。硬化膜が形成された石英基板を、オーブン内で100℃、1,000時間加熱した後、前記紫外可視分光光度計を用いて、波長400nmにおける透過率を測定した。1,000時間加熱前の波長400nmにおける透過率に対して、5%以上の透過率増減がある場合は“×”、透過率増減が5%未満である場合は“○”と評価した。評価結果を表2に示す。
実施例1乃至実施例6で調製したポジ型感光性樹脂組成物を用い、前記[透明性評価]に記載した手順により、硬化膜を石英基板上に形成した。硬化膜が形成された石英基板を、内部が85℃及び相対湿度85%に保持された恒温恒湿槽内で1,000時間保管した後、前記紫外可視分光光度計を用いて、波長400nmにおける透過率を測定した。1,000時間保管前の波長400nmにおける透過率に対して、5%以上の透過率増減がある場合は“×”、透過率増減が5%未満である場合は“○”と評価した。評価結果を表2に示す。
実施例1乃至実施例6で調製したポジ型感光性樹脂組成物を用い、前記[透明性評価]に記載した手順により硬化膜を石英基板上に形成した。硬化膜が形成された石英基板にカットフィルター(L38、(株)渋谷光学製)を装着し、キセノンアーク試験機(Q-SUNXe-1、Q-Lab社製)内で2500万[lx・h]露光した後、前記紫外可視分光光度計を用いて、波長400nmにおける透過率を測定した。前記キセノンアーク試験機による露光前の波長400nmにおける透過率に対して、5%以上の透過率増減がある場合は“×”、透過率増減が5%未満である場合は“○”と評価した。
Claims (14)
- 前記(a2)エポキシ環を含有するモノマーは下記式(2)で表されるモノマーであり、前記(a3)酸解離定数pKaが14以上であるヒドロキシ基を含有するモノマーは下記式(3)で表されるモノマーである、請求項1に記載のポジ型感光性樹脂組成物。
(式中、R0はそれぞれ独立に水素原子又はメチル基を表し、R3は下記式(I)で表される2価の有機基を表し、R4は下記式(4)又は下記式(5)で表される1価の有機基を表し、R5は下記式(I´)で表される1価の有機基を表す。)
(式中、cは0乃至3の整数を表し、dは1乃至3の整数を表し、eはそれぞれ独立に2乃至6の整数を表し、*は前記式(2)又は前記式(3)で表されるモノマーのアルケニル基との結合手を表し、・は前記式(4)又は前記式(5)で表される1価の有機基との結合手を表す。) - 前記(A)成分のポリスチレン換算重量平均分子量は5,000乃至30,000である、請求項1乃至請求項3のいずれか一項に記載のポジ型感光性樹脂組成物。
- 前記(C)成分は非イオン性光酸発生剤である、請求項1乃至請求項4のいずれか一項に記載のポジ型感光性樹脂組成物。
- 下記(D)成分をさらに含有する、請求項1乃至請求項6のいずれか一項に記載のポジ型感光性樹脂組成物。
(D)成分:多官能エポキシ化合物 - 下記(E)成分をさらに含有する、請求項1乃至請求項7のいずれか一項に記載のポジ型感光性樹脂組成物。
(E)成分:増感剤 - マイクロレンズ作製用である、請求項1乃至請求項8のいずれか一項に記載のポジ型感光性樹脂組成物。
- 請求項1乃至請求項9のいずれか一項に記載のポジ型感光性樹脂組成物から得られる硬化膜。
- 請求項1乃至請求項9のいずれか一項に記載のポジ型感光性樹脂組成物から作製されるマイクロレンズ。
- 請求項1乃至請求項9のいずれか一項に記載のポジ型感光性樹脂組成物を基材上に塗布して樹脂膜を形成する塗布工程、前記塗布工程の後に樹脂膜の少なくとも一部を露光する第一露光工程、前記第一露光工程の後に前記樹脂膜の露光部を現像液により除去して該樹脂膜の未露光部のパターンを形成する現像工程、前記現像工程の後に前記パターンをさらに露光する第二露光工程、及び前記第二露光工程の後に前記パターンを130℃以下の温度で加熱するポストベーク工程を含む、マイクロレンズの作製方法。
- 前記現像工程の後及び前記第二露光工程の前に、前記パターンを130℃以下の温度で加熱するリフロー工程を含む、請求項12に記載のマイクロレンズの作製方法。
- 前記基材は、カラーフィルターが形成された基板である、請求項12又は請求項13に記載のマイクロレンズの作製方法。
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JP2009282512A (ja) * | 2008-04-23 | 2009-12-03 | Mitsubishi Rayon Co Ltd | 感光性樹脂組成物およびパターン形成方法 |
JP2012226044A (ja) * | 2011-04-18 | 2012-11-15 | Hitachi Chem Co Ltd | ポジ型感光性樹脂組成物、レジストパターンの製造方法、半導体装置及び電子デバイス |
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JP2009282512A (ja) * | 2008-04-23 | 2009-12-03 | Mitsubishi Rayon Co Ltd | 感光性樹脂組成物およびパターン形成方法 |
JP2012226044A (ja) * | 2011-04-18 | 2012-11-15 | Hitachi Chem Co Ltd | ポジ型感光性樹脂組成物、レジストパターンの製造方法、半導体装置及び電子デバイス |
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