JP7406181B2 - 感光性樹脂組成物 - Google Patents
感光性樹脂組成物 Download PDFInfo
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- JP7406181B2 JP7406181B2 JP2019570723A JP2019570723A JP7406181B2 JP 7406181 B2 JP7406181 B2 JP 7406181B2 JP 2019570723 A JP2019570723 A JP 2019570723A JP 2019570723 A JP2019570723 A JP 2019570723A JP 7406181 B2 JP7406181 B2 JP 7406181B2
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- photosensitive resin
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- 239000011342 resin composition Substances 0.000 title claims description 77
- -1 Polysiloxane Polymers 0.000 claims description 130
- 239000002904 solvent Substances 0.000 claims description 60
- 125000000962 organic group Chemical group 0.000 claims description 54
- 229920005989 resin Polymers 0.000 claims description 42
- 239000011347 resin Substances 0.000 claims description 42
- 125000003700 epoxy group Chemical group 0.000 claims description 30
- 229920001296 polysiloxane Polymers 0.000 claims description 30
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 125000001153 fluoro group Chemical group F* 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 125000003277 amino group Chemical group 0.000 claims description 20
- 239000004642 Polyimide Substances 0.000 claims description 18
- 229920001721 polyimide Polymers 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 238000004132 cross linking Methods 0.000 claims description 10
- 239000003431 cross linking reagent Substances 0.000 claims description 10
- 239000002243 precursor Substances 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- 229920001187 thermosetting polymer Polymers 0.000 claims description 5
- 239000004925 Acrylic resin Substances 0.000 claims description 4
- 229920000178 Acrylic resin Polymers 0.000 claims description 4
- 206010034972 Photosensitivity reaction Diseases 0.000 claims description 4
- 230000036211 photosensitivity Effects 0.000 claims description 4
- 238000005192 partition Methods 0.000 claims description 2
- 239000000306 component Substances 0.000 claims 1
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- 239000010408 film Substances 0.000 description 71
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 23
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 19
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- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 14
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- 125000005370 alkoxysilyl group Chemical group 0.000 description 12
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- 230000018109 developmental process Effects 0.000 description 10
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 10
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- 150000003254 radicals Chemical class 0.000 description 9
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 8
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- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 8
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
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- 125000003545 alkoxy group Chemical group 0.000 description 7
- 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 7
- 239000003822 epoxy resin Substances 0.000 description 7
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- 238000011156 evaluation Methods 0.000 description 7
- 229940095102 methyl benzoate Drugs 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 125000003566 oxetanyl group Chemical group 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 7
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 7
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- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 6
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 6
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- UTSYWKJYFPPRAP-UHFFFAOYSA-N n-(butoxymethyl)prop-2-enamide Chemical compound CCCCOCNC(=O)C=C UTSYWKJYFPPRAP-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
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- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 5
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- 239000000654 additive Substances 0.000 description 5
- 125000004849 alkoxymethyl group Chemical group 0.000 description 5
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 5
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 5
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- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 5
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 5
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
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- AQOSPGCCTHGZFL-UHFFFAOYSA-N 1-(3a-hydroxy-7-methoxy-1,2,4,8b-tetrahydropyrrolo[2,3-b]indol-3-yl)ethanone Chemical compound COC1=CC=C2NC3(O)N(C(C)=O)CCC3C2=C1 AQOSPGCCTHGZFL-UHFFFAOYSA-N 0.000 description 3
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- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 3
- YOZHLACIXDCHPV-UHFFFAOYSA-N n-(methoxymethyl)-2-methylprop-2-enamide Chemical compound COCNC(=O)C(C)=C YOZHLACIXDCHPV-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
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- 239000004065 semiconductor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical group SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- PMQIWLWDLURJOE-UHFFFAOYSA-N triethoxy(1,1,2,2,3,3,4,4,5,5,6,6,7,7,10,10,10-heptadecafluorodecyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CCC(F)(F)F PMQIWLWDLURJOE-UHFFFAOYSA-N 0.000 description 1
- ZLGWXNBXAXOQBG-UHFFFAOYSA-N triethoxy(3,3,3-trifluoropropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)F ZLGWXNBXAXOQBG-UHFFFAOYSA-N 0.000 description 1
- UVSMIEOWIMUEOU-UHFFFAOYSA-N triethoxy(8-fluorooctyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCCCCF UVSMIEOWIMUEOU-UHFFFAOYSA-N 0.000 description 1
- SAWDTKLQESXBDN-UHFFFAOYSA-N triethoxy(heptyl)silane Chemical compound CCCCCCC[Si](OCC)(OCC)OCC SAWDTKLQESXBDN-UHFFFAOYSA-N 0.000 description 1
- OYGYKEULCAINCL-UHFFFAOYSA-N triethoxy(hexadecyl)silane Chemical compound CCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC OYGYKEULCAINCL-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
- FHVAUDREWWXPRW-UHFFFAOYSA-N triethoxy(pentyl)silane Chemical compound CCCCC[Si](OCC)(OCC)OCC FHVAUDREWWXPRW-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- WDUXKFKVDQRWJN-UHFFFAOYSA-N triethoxysilylmethyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)COC(=O)C=C WDUXKFKVDQRWJN-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- HILHCDFHSDUYNX-UHFFFAOYSA-N trimethoxy(pentyl)silane Chemical compound CCCCC[Si](OC)(OC)OC HILHCDFHSDUYNX-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 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
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
-
- 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
- G03F7/0223—Iminoquinonediazides; Para-quinonediazides
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
-
- 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
- G03F7/075—Silicon-containing compounds
-
- 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
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
-
- G—PHYSICS
- G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
- G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
- G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
- G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/10—OLED displays
- H10K59/12—Active-matrix OLED [AMOLED] displays
- H10K59/122—Pixel-defining structures or layers, e.g. banks
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/24—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen halogen-containing groups
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- Crystallography & Structural Chemistry (AREA)
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Materials For Photolithography (AREA)
- Electroluminescent Light Sources (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
より詳細には、高い撥水性と撥油性を硬化膜表面に有する画像を形成可能な感光性樹脂組成物及びその硬化膜、並びに該硬化膜を用いた各種材料に関する。この感光性樹脂組成物は、特に液晶ディスプレイやELディスプレイにおける層間絶縁膜、インクジェット方式に対応した遮光材料や隔壁材料として用いるのに好適である。
しかしインクジェット法でバンクに囲まれた領域にインク滴を滴下する場合、バンクを超えて隣の画素にインク滴が溢れる事態を防ぐため、基板には親インク性(親水性、親油性)を持たせ、バンク表面には撥水性と撥油性を持たせる必要がある。
1.下記(A)成分、(B)成分、(C)溶剤及び(D)成分を含有する熱硬化可能な感光性樹脂組成物。
(A)成分:下記基(A1)及び(A2)を有するポリシロキサン
(A1)フッ素原子を有する有機基
(A2)熱架橋性基を有する有機基
(B)成分:アルカリ可溶性樹脂
(C)溶剤、
(D)成分:感光剤。
2.(A2)熱架橋性基を有する有機基は、エポキシ基を有する有機基である上記1に記載の感光性樹脂組成物。
3.下記(Z1)乃至(Z4)の少なくともいずれか1つを満足する上記1または2に記載の感光性樹脂組成物。
(Z1):(E)成分である架橋剤をさらに含有する、
(Z2):(B)成分のアルカリ可溶性樹脂が、自己架橋性基をさらに有するか、又はヒドロキシ基、カルボキシル基、アミド基及びアミノ基からなる群から選ばれる少なくとも1つの基と反応する基をさらに有する。
(Z3):(D)成分が光ラジカル発生剤であり、さらに(F)成分であるエチレン性二重結合を2個以上有する化合物を含有する。
(Z4):(D)成分が光酸発生剤であり、さらに(G)成分である酸により共有結合を形成する官能基を2個以上有する化合物を含有する。
4.(D)成分がキノンジアジド化合物である上記1または2に記載の感光性樹脂組成物。
5.(D)成分がキノンジアジド化合物であり、上記(Z1)及び(Z2)の何れかを満足する上記3に記載の感光性樹脂組成物。
6.(A)成分がさらにフェニル基を有する上記1乃至5のいずれかに記載の感光性樹脂組成物。
7.(A)成分のポリシロキサンの数平均分子量がポリスチレン換算で1,000乃至100,000である上記6に記載の感光性樹脂組成物。
8.(B)成分のアルカリ可溶性樹脂の数平均分子量がポリスチレン換算で2,000乃至50,000である上記1乃至7のいずれか1つに記載の型感光性樹脂組成物。
9.(B)成分100質量部に対して0.1~20質量部の(A)成分を含有することを特徴とする上記1乃至8のいずれか1つに記載の型感光性樹脂組成物。
10.(A)成分と(B)成分の合計100質量部に対して、(D)成分が5乃至100質量部であることを特徴とする請求項1乃至9のいずれか一項に記載の感光性樹脂組成物。
11.(A)成分と(B)成分の合計100質量部に対して、(E)成分が1乃至50質量部であることを特徴とする上記3乃至10のいずれか1つに記載の感光性樹脂組成物。
12.上記1乃至11のいずれか1つに記載の感光性樹脂組成物を用いて得られる硬化膜。
13.上記12に記載の硬化膜を有する表示素子。
14.上記12に記載の硬化膜を画像形成用隔壁として有する表示素子。
(A)成分:下記基(A1)及び(A2)を有するポリシロキサン
(A1)フッ素原子を有する有機基
(A2)熱架橋性基を有する有機基
(B)成分:アルカリ可溶性樹脂;
(C)溶剤、
(D)成分:感光剤。
(Z1):(E)成分である架橋剤をさらに含有する、
(Z2):(B)成分のアルカリ可溶性樹脂が、自己架橋性基をさらに有するか、又はヒドロキシ基、カルボキシル基、アミド基及びアミノ基からなる群から選ばれる少なくとも1つの基と反応する基をさらに有する。
(Z3):(D)成分が光ラジカル発生剤であり、さらに(F)成分であるエチレン性重合性基を2個以上有する化合物を含有する。
(Z4):(D)成分が光酸発生剤であり、さらに(G)成分である酸により共有結合を形成する官能基を2個以上有する化合物を含有する。
<(A)成分>
本発明に用いるポリシロキサン(A)は、下記基(A1)及び(A2)を有するポリシロキサンである。
(A1)フッ素原子を有する有機基
(A2)熱架橋性基を有する有機基
さらに、熱架橋性基がエポキシ基の場合に、エポキシ基を有する有機基としては、グリシジルオキシ基、3,4-エポキシシクロヘキシルメチル基等が挙げられる。
ポリシロキサン(A)の熱架橋性基を有する有機基は、撥液性付与と膜硬度及び溶剤耐性との両立の観点から、ポリシロキサン(A)が有する全ケイ素原子の1モルに対して0.2~0.95モルが好ましく、0.3~0.8モルがさらに好ましい。
これらの具体例を挙げると、例えば、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、ヘプチル基、オクチル基、ドデシル基、ヘキサデシル基、オクタデシル基、シクロヘキシル基、フェニル基、ビニル基、γ-アミノプロピル基、γ-メタクリロキシプロピル基などが挙げられる。
より具体的に、グリシドキシ基または3,4-エポキシシクロヘキシルメチル基を有する炭素数2~12の有機基が好ましい。
さらに、熱により架橋反応が起こる3-グリシジルオキシプロピル(ジメトキシ)メチルシラン、3-グリシジルオキシプロピル(ジエトキシ)メチルシラン、3-グリシジルオキシプロピルトリメトキシシランまたは2-(3,4-エポキシシクロヘキシル)エチルトリメトキシシランを用いることも好ましい。
例えば、テトラメトキシシラン、テトラエトキシシラン、メチルトリメトキシシラン、メチルトリエトキシシラン、エチルトリメトキシシラン、エチルトリエトキシシラン、プロピルトリメトキシシラン、プロピルトリエトキシシラン、ブチルトリメトキシシラン、ブチルトリエトキシシラン、ペンチルトリメトキシシラン、ペンチルトリエトキシシラン、ヘプチルトリメトキシシラン、ヘプチルトリエトキシシラン、オクチルトリメトキシシラン、オクチルトリエトキシシラン、ドデシルトリメトキシシラン、ドデシルトリエトキシシラン、ヘキサデシルトリメトキシシラン、ヘキサデシルトリエトキシシラン、オクタデシルトリメトキシシラン、オクタデシルトリエトキシシランなどのアルキルトリアルコキシシラン、フェニルトリメトキシシラン、フェニルトリエトキシシラン、ベンジルトリメトキシシラン及びベンジルトリエトキシシランなどの芳香族基を有するトリアルコキシシラン、ジメチルジメトキシシラン、ジメチルジエトキシシランなどのジアルコキシシラン、シクロヘキシルトリエトキシシラン、シクロヘキシルトリメトキシシラン、アリルトリエトキシシラン、アリルトリメトキシシラン、ジエトキシメチルビニルシラン、ジメトキシメチルビニルシラン、トリエトキシビニルシラン、ビニルトリメトキシシラン、ビニルトリス(2-メトキシエトキシ)シラン、m-スチリルエチルトリエトキシシラン、p-スチリルエチルトリエトキシシラン、m-スチリルメチルトリエトキシシラン、p-スチリルメチルトリエトキシシラン、3-(N-スチリルメチル-2-アミノエチルアミノ)プロピルトリメトキシシラン、3-(2-アミノエチルアミノ)プロピルジメトキシメチルシラン、3-(2-アミノエチルアミノ)プロピルトリエトキシシラン、3-(2-アミノエチルアミノ)プロピルトリメトキシシラン、3-アミノプロピルジエトキシメチルシラン、3-アミノプロピルトリエトキシシラン、3-アミノプロピルトリメトキシシラン、トリメトキシ[3-(フェニルアミノ)プロピル]シラン、3-メルカプトプロピル(ジメトキシ)メチルシラン、(3-メルカプトプロピル)トリエトキシシラン、(3-メルカプトプロピル)トリメトキシシラン、3-(トリエトキシシリル)プロピルイソシアネート、3-(トリエトキシシリル)プロピルメタクリレート、3-(トリメトキシシリル)プロピルメタクリレート、3-(トリエトキシシリル)プロピルアクリレート、3-(トリメトキシシリル)プロピルアクリレート、2-(トリエトキシシリル)エチルメタクリレート、2-(トリメトキシシリル)エチルメタクリレート、2-(トリエトキシシリル)エチルアクリレート、2-(トリメトキシシリル)エチルアクリレート、(トリエトキシシリル)メチルメタクリレート、(トリメトキシシリル)メチルメタクリレート、(トリエトキシシリル)メチルアクリレート、(トリメトキシシリル)メチルアクリレート、γ-ウレイドプロピルトリエトキシシラン、γ-ウレイドプロピルトリメトキシシラン、γ-ウレイドプロピルトリプロポキシシラン、(R)-N-1-フェニルエチル-N’-トリエトキシシリルプロピルウレア、(R)-N-1-フェニルエチル-N’-トリメトキシシリルプロピルウレア、1-[3-(トリメトキシシリル)プロピル]ウレアなどが挙げられる。
上記水酸化テトラエチルアンモニウム水溶液の存在量は、使用するアルコキシシランが有する全アルコキシ基量の1モルに対し、好ましくは0.01~0.2モルとされる。上記加熱は、液温が好ましくは0~100℃で行うことができ、また、液の蒸発、揮散などが起こらないように、好ましくは、還流管を備え付けた容器中の還流下で数十分~十数時間行われる。
アルコキシシランを重縮合する際には、仕込んだアルコキシシランの全ケイ素原子を酸化物に換算した濃度(以下、SiO2換算濃度と称す。)が、40質量%以下、特に好ましくは10~30質量%の範囲で加熱されることが好ましい。このような濃度範囲で任意の濃度を選択することにより、ゲルの生成を抑え、均質なポリシロキサン含有溶液を得ることができる。
本発明においては、上記の有機溶媒を複数種混合して用いてもよい。
本発明の(B)成分は、アルカリ可溶性基を有する樹脂である。アルカリ可溶性基としては、例えば、フェノール性ヒドロキシ基、カルボキシル基、酸無水物基、イミド基、スルホニル基、リン酸、ボロン酸及び活性メチレン基および活性メチン基が挙げられる。
そのようなアルキル基としては、例えば、メチル基、エチル基、n-プロピル基、i-プロピル基等が挙げられる。
その中でも、メチル基、エチル基、n-プロピル基等が好ましい。
そのようなアルコキシ基としては、例えば、メトキシ基、エトキシ基、n-プロポキシ基、i-プロポキシ基、n-ブトキシ基、i-ブトキシ基、s-ブトキシ基、t-ブトキシ基等が挙げられる。
その中でも、メトキシ基、エトキシ基及びn-プロポキシ基等が好ましい。
カルボキシル基を有するモノマーとしては、例えば、アクリル酸、メタクリル酸、クロトン酸、モノ-(2-(アクリロイルオキシ)エチル)フタレート、モノ-(2-(メタクリロイルオキシ)エチル)フタレート、N-(カルボキシフェニル)マレイミド、N-(カルボキシフェニル)メタクリルアミド、N-(カルボキシフェニル)アクリルアミド等が挙げられる。
等が挙げられる。
以下、当該その他モノマーの具体例を挙げるが、これらに限定されるものではない。
本発明においては、上記特定共重合体の粉体をそのまま用いても良く、あるいはその粉体を、たとえば後述する(C)溶剤に再溶解して溶液の状態として用いても良い。
これらは、1種単独で用いてもよく、又は2種以上の化合物を組み合わせて用いてもよい。
これらは、1種単独で用いてもよく、又は2種以上の化合物を組み合わせて用いてもよい。
このようなカルボン酸無水物の例としてはフタル酸無水物、トリメリット酸無水物、無水マレイン酸、ナフタル酸無水物、水素化フタル酸無水物、メチル-5-ノルボルネン-2,3-ジカルボン酸無水物、無水イタコン酸、テトラヒドロフタル酸無水物等を挙げることができる。
また、末端アミノ基を酸無水物で保護する場合の反応温度は-20乃至150℃、好ましくは-5乃至100℃の任意の温度を選択することができる。
ポリイミドへのカルボキシル基又はフェノール性ヒドロキシ基の導入方法は、カルボキシル基又はフェノール性ヒドロキシ基を有するモノマーを用いる方法、カルボキシル基又はフェノール性ヒドロキシ基を有する酸無水物でアミン末端を封止する方法、或いは、ポリアミド酸などのポリイミド前駆体をイミド化する際にイミド化率を99%以下にする方法等が用いられる。
化学イミド化の方法としては一般的にポリイミド前駆体溶液に過剰の無水酢酸およびピリジンを添加し室温から100℃で反応させる方法が用いられる。また、熱イミド化の方法としては一般的に、ポリイミド前駆体溶液を温度180℃乃至250℃で脱水しながら過熱する方法が用いられる。
酸二無水物としては、上記(a)テトラカルボン酸二無水物が挙げられる。
ジオールとしては、ビスフェノールA、ビスフェノールF、4,4’-ジヒドロキシビフェニル、ベンゼン-1,3-ジメタノール、ベンゼン-1,4-ジメタノール等の芳香族ジオール、水添ビスフェノールA、水添ビスフェノールF、1,4-シクロヘキサンジオール、1,3-シクロヘキサンジメタノール、1,4-シクロヘキサンジメタノール等の脂環族ジオール、及びエチレングリコール、プロピレングリコール、1,4-ブタンジオール、1,6-ヘキサンジオール等の脂肪族ジオール等が挙げられる。
本発明に用いる(C)溶剤は、(A)成分、(B)成分、及び必要に応じて後述の(D)成分、(E)成分、(F)成分、(G)成分を溶解し、且つ所望により添加される後述の(H)成分やその他添加剤などを溶解するものであり、斯様な溶解能を有する溶剤であれば、その種類及び構造などは特に限定されるものでない。
これら(C)溶剤の中、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テート、2-ヘプタノン、プロピレングリコールプロピルエーテル、プロピレングリコールプロピルエーテルアセテート、乳酸エチル、乳酸ブチル等が、塗膜性が良好で安全性が高いという観点より好ましい。これら溶剤は、一般にフォトレジスト材料のための溶剤として用いられている。
(D)成分である感光剤としては、(D-1)1,2-キノンジアジド化合物、(D-2)光ラジカル発生剤、(D-3)光酸発生剤が挙げられる。
上記の光重合開始剤は、市販品として容易に入手が可能であり、その具体例としては、例えばIRGACURE 173、IRGACURE 500、IRGACURE 2959、IRGACURE 754、IRGACURE 907、IRGACURE 369、IRGACURE 1300、IRGACURE 819、IRGACURE 819DW、IRGACURE 1880、IRGACURE 1870、DAROCURE TPO、DAROCURE 4265、IRGACURE 784、IRGACURE OXE01、IRGACURE OXE02、IRGACURE 250(以上、BASF社製)、KAYACURE DETX-S、KAYACURE CTX、KAYACURE BMS、KAYACURE 2-EAQ(以上、日本化薬(株)製)、TAZ-101、TAZ-102、TAZ-103、TAZ-104、TAZ-106、TAZ-107、TAZ-108、TAZ-110、TAZ-113、TAZ-114、TAZ-118、TAZ-122、TAZ-123、TAZ-140、TAZ-204(以上みどり化学(株)製)等が挙げられる。
これらの光ラジカル発生剤単独で使用しても、二種類以上を併用することも可能である。
(E)成分は架橋剤であり、本発明の感光性樹脂組成物が要件(Z1)を満たす場合に組成物中に導入されるものである。より具体的には、(B)成分の熱反応性部位(たとえば、カルボキシル基及び/又はフェノール性水酸基)と熱反応により橋架け構造を形成しうる構造を有する化合物である。以下、具体例を挙げるがこれらに限定されるものではない。熱架橋剤は、例えば、(E1)アルコキシメチル基及びヒドロキシメチル基から選ばれる置換基を2個以上有する架橋性化合物や(E2)式(5)で表される架橋性化合物から選ばれるものが好ましい。これらの架橋剤は単独または2種以上の組み合わせで使用することができる。
(F)成分はエチレン性重合性基を2個以上有する化合物である。ここで言うところのエチレン性重合性基を2個以上有する化合物とは、一分子中に重合性基を2個以上有し、且つそれらの重合性基が分子末端にある化合物のことを意味し、それらの重合性基とは、アクリレート基、メタクリレート基、ビニル基及びアリル基からなる群より選ばれる少なくとも1種類の重合性基のことを意味する。
この(F)成分であるエチレン性重合性基を2個以上有する化合物は、本発明のネガ型感光性樹脂組成物の溶液において、各成分との相溶性が良好で、且つ現像性に影響を与えないという観点から、分子量(該化合物がポリマーである場合、重量平均分子量)が1,000以下の化合物が好ましい。
これらの重エチレン性合性基を2個以上有する化合物は1種または2種以上を組み合わせて用いることができる。
本発明の感光性樹脂組成物に用いられる(G)成分は、酸により共有結合を形成する官能基を2個以上有する化合物である。このような酸により共有結合を形成する官能基としてはエポキシ基やメチロール基等が挙げられる。
上記エポキシ基を有するポリマーは、例えばエポキシ基を有する付加重合性モノマーを用いた付加重合により製造することができる。一例として、ポリグリシジルアクリレート、グリシジルメタクリレートとエチルメタクリレートの共重合体、グリシジルメタクリレートとスチレンと2-ヒドロキシエチルメタクリレートの共重合体等の付加重合ポリマーや、エポキシノボラック等の縮重合ポリマーを挙げることができる。
更に、本発明の感光性樹脂組成物は、本発明の効果を損なわない限りにおいて、必要に応じて、レオロジー調整剤、顔料、染料、保存安定剤、消泡剤、密着促進剤、または多価フェノール、多価カルボン酸等の溶解促進剤等を含有することができる。
本発明の感光性樹脂組成物は、下記(A)成分、(B)成分、(C)溶剤及び(D)成分を含有する感光性樹脂組成物であり、且つ、所望により、(E)成分の架橋剤、(F)成分の重合性基を2個以上有する化合物、(G)成分の酸により共有結合を形成する官能基を2個以上有する化合物、及びその他添加剤のうち一種以上を更に含有することができる組成物である。
(A)成分:下記基(A1)及び(A2)を有するポリシロキサン
(A1)フッ素原子を有する有機基
(A2)熱架橋性基を有する有機基
(B)成分:アルカリ可溶性樹脂
(C)溶剤、
(D)成分:感光剤。
[1]:(B)成分100質量部に対して0.1~20質量部の(A)成分を含有し、これら成分が(C)溶剤に溶解された感光性樹脂組成物。
[2]:(B)成分100質量部に対して0.1~20質量部の(A)成分、5乃至100質量部の(D)成分を含有し、これら成分が(C)溶剤に溶解された感光性樹脂組成物。
[3]:(B)成分100質量部に対して0.1~20質量部の(A)成分、5乃至100質量部の(D)成分を含有し、これら成分が(C)溶剤に溶解された感光性樹脂組成物であって、さらに(E)成分である架橋剤を、(A)成分と(B)成分の合計の100質量部に対して1乃至50質量部含有する感光性樹脂組成物。
本発明の感光性樹脂組成物を半導体基板(例えば、シリコン/二酸化シリコン被覆基板、シリコンナイトライド基板、金属(例えばアルミニウム、モリブデン、クロム)などが被覆された基板、ガラス基板、石英基板、ITO基板等)の上に、回転塗布、流し塗布、ロール塗布、スリット塗布、スリットに続いた回転塗布、インクジェット塗布などによって塗布し、その後、ホットプレートまたはオーブン等で予備乾燥することにより、塗膜を形成することができる。その後、この塗膜を加熱処理することにより、感光性樹脂膜が形成される。
[数平均分子量及び重量平均分子量の測定]
以下の合成例に従い得られた共重合体の数平均分子量及び重量平均分子量を、島津製作所製GPC装置(ShodexカラムKF-804Lおよび803L)を用い、溶出溶媒テトラヒドロフランを流量1ml/分でカラム中に(カラム温度40℃)流して溶離させるという条件で測定した。なお、下記の数平均分子量(以下、Mnと称す。)及び重量平均分子量(以下、Mwと称す。)は、ポリスチレン換算値にて表される。
MMA:メチルメタクリレート
HEMA:2-ヒドロキシエチルメタクリレート
HPMA:4-ヒドロキシフェニルメタクリレート
HPMA-QD:4-ヒドロキシフェニルメタクリレート1molと1,2-ナフトキノン-2-ジアジド-5-スルホニルクロリド1.1molとの縮合反応によって合成される化合物
CHMI:N-シクロヘキシルマレイミド
TMSSMA:メタクリルオキシプロピルトリス(トリメチルシロキシ)シラン
PFHMA:2-(パーフルオロヘキシル)エチルメタクリレート
MAA:メタクリル酸
AIBN:α、α’-アゾビスイソブチロニトリル
QD:α、α、α’-トリス(4-ヒドロキシフェニル)-1-エチル-4-イソプロピルベンゼン1molと1,2-ナフトキノン-2-ジアジド-5-スルホニルクロリド2molとの縮合反応によって合成される化合物
GT-401:ブタンテトラカルボン酸 テトラ(3,4-エポキシシクロヘキシルメチル) 修飾ε-カプロラクトン
P2:ヒドロキシスチレン85%とスチレン15%の重合体と、ヒドロキシスチレン70%とスチレン30%の重合体とを2:8で混合したスチレン重合体
PFHTMOS:2-(パーフルオロヘキシル)エチルトリメトキシシラン
KBM-503:3-メタクリロキシプロピルトリメトキシシラン
KBM-403:3-グリシドキシプロピルトリメトキシシラン
KBM-303:2-(3,4-エポキシシクロヘキシル)エチルトリメトキシシラン
35wt%TEAH:35wt%水酸化テトラエチルアンモニウム水溶液
PTMOS:フェニルトリメトキシシラン
15JWET:オルガノ社製イオン交換樹脂
I907:2-メチルー1-[4-(メチルチオ)フェニル]-2-モルフォリノプロパンー1-オン(IRGACURE 907、BASF製)
DEAB:4,4’-ビス(ジエチルアミノ)ベンゾフェノン
DPHA:ジペンタエリスリトールヘキサアクリレート
8KQ:8KQ-2001(大成ファインケミカル(株)製 アルカリ可溶UV硬化型アクリル樹脂)(P8)
PGME:プロピレングリコールモノメチルエーテル
PGMEA:プロピレングリコールモノメチルエーテルアセテート
CHN:シクロヘキサノン
THF:テトラヒドロフラン
MAA 70.00g、HEMA 218.75g、HPMA 43.75g、MMA 192・50g、CHMI 350.00g、AIBN 56.00gをPGME 1396.50gに溶解し、90℃にて20時間反応させることによりアクリル重合体溶液(固形分濃度40質量%)を得た(P1)。得られたアクリル重合体のMnは2,800、Mwは4,900であった。
PFHTMOS 2.34g、KBM-303 4.93g、35wt%TEAH 0.21g、水 0.68gをTHF 9.79gに溶解し、40℃にて4時間撹拌した。続いて、THFで洗浄した15JWET 0.73gを添加し、25℃にて1時間撹拌した。次いで、廃15JWETをろ過しシロキサン重合体溶液を得た(P3)。得られたシロキサン重合体のMnは1,900、Mwは2,200であった。
PFHTMOS 2.34g、KBM-403 4.45g、35wt%TEAH 0.21g、水 0.68gをTHF 9.21gに溶解し、40℃にて4時間撹拌した。続いて、THFで洗浄した15JWET 0.68gを添加し、25℃にて1時間撹拌した。次いで、廃15JWETをろ過しシロキサン重合体溶液を得た(P4)。得られたシロキサン重合体のMnは2,400、Mwは2,900であった。
PFHTMOS 2.34g、KBM-303 2.46g、PTMOS 1.98g、35wt%TEAH 0.21g、水 0.68gをTHF 9.21gに溶解し、40℃にて4時間撹拌した。続いて、THFで洗浄した15JWET 0.48gを添加し、25℃にて1時間撹拌した。次いで、廃15JWETをろ過しシロキサン重合体溶液を得た(P5)。得られたシロキサン重合体のMnは1,900、Mwは2,400であった。
HPMA-QD 2.50g、TMSSMA 2.58g、PFHMA 5.26g、MAA 0.70g、CHMI 1.46g、AIBN 0.33gをCHN 51.3gに溶解し、110℃にて20時間撹拌させることによりアクリル重合体溶液(固形分濃度20質量%)を得た(P6)。得られたアクリル重合体のMnは7,200、Mwは11,000であった。
PFHTMOS 2.34g、KBM-503 4.97g、35wt%TEAH 0.21g、水 0.68gをTHF 9.83gに溶解し、40℃にて4時間撹拌した。続いて、THFで洗浄した15JWET 0.73gを添加し、25℃にて1時間撹拌した。次いで、廃15JWETをろ過しシロキサン重合体溶液を得た(P7)。得られたシロキサン重合体のMnは2,000、Mwは2,100であった。
次の表1に示す組成に従い、(A)成分の溶液、(B)成分の溶液、(D)成分、(E)成分、(F)成分を所定の割合で(C)溶剤に溶解し、室温で3時間撹拌して均一な溶液とすることにより、各実施例及び各比較例の感光性樹脂組成物を調製した。
感光性樹脂組成物をシリコンウェハ上にスピンコーターを用いて塗布した後、温度80℃で120秒間ホットプレート上においてプリベークを行い、膜厚1.2μmの塗膜を形成した。この塗膜を2.38質量%の水酸化テトラメチルアンモニウム(以下、TMAHと称す)水溶液に60秒間浸漬した後、超純水で30秒間流水洗浄を行った。次いでこの塗膜を温度230℃で30分間加熱することによりポストベークを行い、膜厚1.0μmの硬化膜を形成した。この硬化膜上の安息香酸メチルの接触角を協和界面科学(株)製Drop Masterを用いて測定した。得られた結果を表2に示す。
[接触角の評価:実施例4、実施例5及び比較例4]
感光性樹脂組成物をシリコンウェハ上にスピンコーターを用いて塗布した後、温度100℃で120秒間ホットプレート上においてプリベークを行い、膜厚1.2μmの塗膜を形成した。この塗膜を0.4質量%TMAH水溶液に60秒間浸漬した後、超純水で30秒間流水洗浄を行った。次いでこの塗膜を温度230℃で30分間加熱することによりポストベークを行い、膜厚1.0μmの硬化膜を形成した。この硬化膜上の安息香酸メチルの接触角を協和界面科学(株)製Drop Masterを用いて測定した。得られた結果を表2に示す。
感光性樹脂組成物をシリコンウェハ上にスピンコーターを用いて塗布した後、温度80℃で120秒間ホットプレート上においてプリベークを行い、膜厚1.2μmの塗膜を形成した。この塗膜を2.38質量%TMAH水溶液に60秒間浸漬した後、超純水で30秒間流水洗浄を行った。次いでこの塗膜を温度230℃で30分間加熱することによりポストベークを行い、膜厚1.0μmの硬化膜を形成した。この硬化膜を(株)テクノビジョン製UV-312を用いて10分間オゾン洗浄した。オゾン洗浄処理した膜上の安息香酸メチルの接触角を協和界面科学(株)製Drop Masterを用いて測定した。得られた結果を表2に示す。ポストベーク後とUVオゾン処理後の差が20°以内のものを良好とする。
[UVオゾン処理耐性の評価:実施例4、実施例5及び比較例4]
感光性樹脂組成物をシリコンウェハ上にスピンコーターを用いて塗布した後、温度100℃で120秒間ホットプレート上においてプリベークを行い、膜厚1.2μmの塗膜を形成した。この塗膜を0.4質量%TMAH水溶液に60秒間浸漬した後、超純水で30秒間流水洗浄を行った。次いでこの塗膜を温度230℃で30分間加熱することによりポストベークを行い、膜厚1.0μmの硬化膜を形成した。この硬化膜を(株)テクノビジョン製UV-312を用いて10分間オゾン洗浄した。オゾン洗浄処理した膜上の安息香酸メチルの接触角を協和界面科学(株)製Drop Masterを用いて測定した。得られた結果を表2に示す。ポストベーク後とUVオゾン処理後の差が20°以内のものを良好とする。
感光性樹脂組成物をITO-ガラス上にスピンコーターを用いて塗布した後、温度80℃で120秒間ホットプレート上においてプリベークを行い、膜厚1.2μmの塗膜を形成した。この塗膜に長さ50μm、幅100μmの長方形パターンのマスクを介しキヤノン(株)製紫外線照射装置PLA-600FAにより365nmにおける光強度が5.5mW/cm2の紫外線を一定時間照射した。その後2.38質量%TMAH水溶液に60秒間浸漬することで現像を行った後、超純水で30秒間流水洗浄を行った。次いでこの長方形パターンが形成された塗膜を温度230℃で30分間加熱することによりポストベークを行い硬化させた。得られた硬化膜の長方形開口部上にクラスターテクノロジー(株)製 Inkjet Designerを用いて駆動波形:A、繰り返し周波数:1kHz、駆動電圧:4Vで約20plの溶液を吐出した。吐出溶液は安息香酸メチルを使用した。得られた結果を表3に示す。
[濡れ性の評価:実施例4、実施例5及び比較例4]
感光性樹脂組成物をITO-ガラス上にスピンコーターを用いて塗布した後、温度100℃で120秒間ホットプレート上においてプリベークを行い、膜厚1.2μmの塗膜を形成した。この塗膜に長さ50μm、幅100μmの長方形パターンのマスクを介しキヤノン(株)製紫外線照射装置PLA-600FAにより365nmにおける光強度が5.5mW/cm2の紫外線を一定時間照射した。その後0.4質量%TMAH水溶液に60秒間浸漬することで現像を行った後、超純水で30秒間流水洗浄を行った。次いでこの長方形パターンが形成された塗膜を温度230℃で30分間加熱することによりポストベークを行い硬化させた。得られた硬化膜の長方形開口部上にクラスターテクノロジー(株)製 Inkjet Designerを用いて駆動波形:A、繰り返し周波数:1kHz、駆動電圧:4Vで約20plの溶液を吐出した。吐出溶液は安息香酸メチルを使用した。得られた結果を表3に示す。
Claims (12)
- 下記(A)成分、(B)成分、(C)溶剤及び(D)成分を含有する熱硬化可能な感光性樹脂組成物。
(A)成分:下記基(A1)及び(A2)を有するポリシロキサン
(A1)フッ素原子を有する有機基
(A2)エポキシ基を有する有機基
(B)成分:アクリル系樹脂、ポリヒドロキシスチレン系樹脂、ポリイミド前駆体又はポリイミドであるアルカリ可溶性樹脂
(C)溶剤、
(D)成分:キノンジアジド化合物。 - (B)成分がアクリル系樹脂又はポリヒドロキシスチレン系樹脂である請求項1に記載の感光性樹脂組成物。
- 下記(Z1)及び(Z2)の少なくともいずれか1つを満足する請求項1または請求項2に記載の感光性樹脂組成物。
(Z1):(E)成分である架橋剤をさらに含有する、
(Z2):(B)成分のアルカリ可溶性樹脂が、自己架橋性基をさらに有するか、又はヒドロキシ基、カルボキシル基、アミド基及びアミノ基からなる群から選ばれる少なくとも1つの基と反応する基をさらに有する。 - (A)成分がさらにフェニル基を有する請求項1に記載の感光性樹脂組成物。
- (A)成分のポリシロキサンの数平均分子量がポリスチレン換算で1,000乃至100,000である請求項1に記載の感光性樹脂組成物。
- (B)成分のアルカリ可溶性樹脂の数平均分子量がポリスチレン換算で2,000乃至50,000である請求項1乃至5のいずれか一項に記載の感光性樹脂組成物。
- (B)成分100質量部に対して0.1~20質量部の(A)成分を含有することを特徴とする請求項1乃至6のいずれか一項に記載の感光性樹脂組成物。
- (A)成分と(B)成分の合計100質量部に対して、(D)成分が5乃至100質量部であることを特徴とする請求項1乃至7のいずれか一項に記載の感光性樹脂組成物。
- (A)成分と(B)成分の合計100質量部に対して、(E)成分が1乃至50質量部であることを特徴とする請求項3乃至8のいずれか一項に記載の感光性樹脂組成物。
- 請求項1乃至9のいずれか一項に記載の感光性樹脂組成物を用いて得られる硬化膜。
- 請求項10に記載の硬化膜を有する表示素子。
- 請求項10に記載の硬化膜を画像形成用隔壁として有する表示素子。
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