TWI795489B - Chemically amplified positive photosensitive resin composition and application thereof - Google Patents
Chemically amplified positive photosensitive resin composition and application thereof Download PDFInfo
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- TWI795489B TWI795489B TW107145347A TW107145347A TWI795489B TW I795489 B TWI795489 B TW I795489B TW 107145347 A TW107145347 A TW 107145347A TW 107145347 A TW107145347 A TW 107145347A TW I795489 B TWI795489 B TW I795489B
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- 239000011342 resin composition Substances 0.000 title claims abstract description 43
- 229920005989 resin Polymers 0.000 claims abstract description 43
- 239000011347 resin Substances 0.000 claims abstract description 43
- 230000001681 protective effect Effects 0.000 claims abstract description 36
- 239000000203 mixture Substances 0.000 claims abstract description 27
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000000178 monomer Substances 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 21
- 125000002723 alicyclic group Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 239000000758 substrate Substances 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003700 epoxy group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 9
- 150000004292 cyclic ethers Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910000077 silane Inorganic materials 0.000 claims description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
- 239000010408 film Substances 0.000 abstract description 77
- 239000000126 substance Substances 0.000 abstract description 20
- 239000010409 thin film Substances 0.000 abstract description 5
- 239000011229 interlayer Substances 0.000 abstract description 4
- 230000003287 optical effect Effects 0.000 abstract description 3
- 239000011162 core material Substances 0.000 abstract description 2
- 239000011247 coating layer Substances 0.000 abstract 1
- -1 mono Carboxylic acid compound Chemical class 0.000 description 99
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 27
- 230000005855 radiation Effects 0.000 description 22
- 239000011248 coating agent Substances 0.000 description 20
- 238000000576 coating method Methods 0.000 description 20
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 18
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 16
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000002202 Polyethylene glycol Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 229920001223 polyethylene glycol Polymers 0.000 description 9
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical compound CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 230000001476 alcoholic effect Effects 0.000 description 6
- 150000005215 alkyl ethers Chemical class 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 150000001923 cyclic compounds Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 125000003566 oxetanyl group Chemical group 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- 229920001296 polysiloxane Polymers 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 3
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 3
- QHGUPRQTQITEPO-UHFFFAOYSA-N oxan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCO1 QHGUPRQTQITEPO-UHFFFAOYSA-N 0.000 description 3
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 229920003002 synthetic resin Polymers 0.000 description 3
- 239000000057 synthetic resin Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CGILRHVKKLYKNE-UHFFFAOYSA-N (3-methyloxetan-3-yl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1(C)COC1 CGILRHVKKLYKNE-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- XXSDRURBACQHHW-UHFFFAOYSA-N 1-cyclohexyloxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)OC1CCCCC1 XXSDRURBACQHHW-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 2
- HVBADOTWUFBZMF-UHFFFAOYSA-N 1-ethoxyethyl 2-methylprop-2-enoate Chemical compound CCOC(C)OC(=O)C(C)=C HVBADOTWUFBZMF-UHFFFAOYSA-N 0.000 description 2
- YRYLWWGGGJOZSB-UHFFFAOYSA-N 1-phenylmethoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)OCC1=CC=CC=C1 YRYLWWGGGJOZSB-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- ZADXFVHUPXKZBJ-UHFFFAOYSA-N 2-[(4-ethenylphenyl)methoxymethyl]oxirane Chemical compound C1=CC(C=C)=CC=C1COCC1OC1 ZADXFVHUPXKZBJ-UHFFFAOYSA-N 0.000 description 2
- OENZCYOCXAUZOT-UHFFFAOYSA-N 2-[2-(2-ethenylphenyl)-1-[2-(2-ethenylphenyl)-1-(oxiran-2-yl)ethoxy]ethyl]oxirane Chemical compound C=CC1=CC=CC=C1CC(C1OC1)OC(C1OC1)CC1=CC=CC=C1C=C OENZCYOCXAUZOT-UHFFFAOYSA-N 0.000 description 2
- CWMLFHKGLMSMPE-UHFFFAOYSA-N 2-[2-(3-ethenylphenyl)-1-[2-(3-ethenylphenyl)-1-(oxiran-2-yl)ethoxy]ethyl]oxirane Chemical compound C=CC1=CC=CC(CC(OC(CC=2C=C(C=C)C=CC=2)C2OC2)C2OC2)=C1 CWMLFHKGLMSMPE-UHFFFAOYSA-N 0.000 description 2
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- LDBOYMRNYCBDQK-UHFFFAOYSA-N 3-(ethenoxymethyl)-3-ethyloxetane Chemical compound C=COCC1(CC)COC1 LDBOYMRNYCBDQK-UHFFFAOYSA-N 0.000 description 2
- VAJVDSVGBWFCLW-UHFFFAOYSA-N 3-Phenyl-1-propanol Chemical compound OCCCC1=CC=CC=C1 VAJVDSVGBWFCLW-UHFFFAOYSA-N 0.000 description 2
- NTKBNCABAMQDIG-UHFFFAOYSA-N 3-butoxypropan-1-ol Chemical compound CCCCOCCCO NTKBNCABAMQDIG-UHFFFAOYSA-N 0.000 description 2
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 2
- BESKSSIEODQWBP-UHFFFAOYSA-N 3-tris(trimethylsilyloxy)silylpropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C BESKSSIEODQWBP-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 description 2
- XNWPXDGRBWJIES-UHFFFAOYSA-N Maclurin Natural products OC1=CC(O)=CC(O)=C1C(=O)C1=CC=C(O)C(O)=C1 XNWPXDGRBWJIES-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 230000003321 amplification Effects 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- FYGUSUBEMUKACF-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carboxylic acid Chemical compound C1C2C(C(=O)O)CC1C=C2 FYGUSUBEMUKACF-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- IKRARXXOLDCMCX-UHFFFAOYSA-N butyl 2-butoxypropanoate Chemical compound CCCCOC(C)C(=O)OCCCC IKRARXXOLDCMCX-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- OTTZHAVKAVGASB-UHFFFAOYSA-N hept-2-ene Chemical compound CCCCC=CC OTTZHAVKAVGASB-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- XLSMFKSTNGKWQX-UHFFFAOYSA-N hydroxyacetone Chemical group CC(=O)CO XLSMFKSTNGKWQX-UHFFFAOYSA-N 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- QBVBLLGAMALJGB-UHFFFAOYSA-N methyl 2-butoxypropanoate Chemical compound CCCCOC(C)C(=O)OC QBVBLLGAMALJGB-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000003199 nucleic acid amplification method Methods 0.000 description 2
- CSVRUJBOWHSVMA-UHFFFAOYSA-N oxolan-2-yl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCO1 CSVRUJBOWHSVMA-UHFFFAOYSA-N 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
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- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229940057867 methyl lactate Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-UHFFFAOYSA-N methylfumaric acid Natural products OC(=O)C(C)=CC(O)=O HNEGQIOMVPPMNR-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-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
- 125000001400 nonyl 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])[H] 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- ZPIRTVJRHUMMOI-UHFFFAOYSA-N octoxybenzene Chemical compound CCCCCCCCOC1=CC=CC=C1 ZPIRTVJRHUMMOI-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AMUUFLNQHMIHRP-UHFFFAOYSA-N oxetan-3-ylmethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1COC1 AMUUFLNQHMIHRP-UHFFFAOYSA-N 0.000 description 1
- ZADZUSCZHASNAH-UHFFFAOYSA-N oxetan-3-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1COC1 ZADZUSCZHASNAH-UHFFFAOYSA-N 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
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- 229920000728 polyester Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- CYIRLFJPTCUCJB-UHFFFAOYSA-N propyl 2-methoxypropanoate Chemical compound CCCOC(=O)C(C)OC CYIRLFJPTCUCJB-UHFFFAOYSA-N 0.000 description 1
- HJIYVZIALQOKQI-UHFFFAOYSA-N propyl 3-butoxypropanoate Chemical compound CCCCOCCC(=O)OCCC HJIYVZIALQOKQI-UHFFFAOYSA-N 0.000 description 1
- IYVPXMGWHZBPIR-UHFFFAOYSA-N propyl 3-ethoxypropanoate Chemical compound CCCOC(=O)CCOCC IYVPXMGWHZBPIR-UHFFFAOYSA-N 0.000 description 1
- JCMFJIHDWDKYIL-UHFFFAOYSA-N propyl 3-methoxypropanoate Chemical compound CCCOC(=O)CCOC JCMFJIHDWDKYIL-UHFFFAOYSA-N 0.000 description 1
- YTUFRRBSSNRYID-UHFFFAOYSA-N propyl 3-propoxypropanoate Chemical compound CCCOCCC(=O)OCCC YTUFRRBSSNRYID-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-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
- 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 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- IXSPLXSQNNZJJU-UHFFFAOYSA-N trimethyl(silyloxy)silane Chemical compound C[Si](C)(C)O[SiH3] IXSPLXSQNNZJJU-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 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
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/02—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having potential barriers; including integrated passive circuit elements having potential barriers
- H01L27/12—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having potential barriers; including integrated passive circuit elements having potential barriers the substrate being other than a semiconductor body, e.g. an insulating body
- H01L27/1214—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having potential barriers; including integrated passive circuit elements having potential barriers the substrate being other than a semiconductor body, e.g. an insulating body comprising a plurality of TFTs formed on a non-semiconducting substrate, e.g. driving circuits for AMLCDs
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/02—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having potential barriers; including integrated passive circuit elements having potential barriers
- H01L27/12—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having potential barriers; including integrated passive circuit elements having potential barriers the substrate being other than a semiconductor body, e.g. an insulating body
- H01L27/1214—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having potential barriers; including integrated passive circuit elements having potential barriers the substrate being other than a semiconductor body, e.g. an insulating body comprising a plurality of TFTs formed on a non-semiconducting substrate, e.g. driving circuits for AMLCDs
- H01L27/1248—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having potential barriers; including integrated passive circuit elements having potential barriers the substrate being other than a semiconductor body, e.g. an insulating body comprising a plurality of TFTs formed on a non-semiconducting substrate, e.g. driving circuits for AMLCDs with a particular composition or shape of the interlayer dielectric specially adapted to the circuit arrangement
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Computer Hardware Design (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Materials For Photolithography (AREA)
Abstract
Description
本發明係有關於一種化學增幅型正型感光性樹脂組成物,及由其形成之保護膜、及具有保護膜之元件。其中,特別是提供一種曝光、顯影後形成顯影密著性佳、耐化性佳等特性之保護膜用正型感光性樹脂組成物。此保護膜適用於液晶顯示元件、有機EL顯示元件等之薄膜電晶體(Thin Film Transistor;TFT)基板用平坦化膜、層間絕緣膜或光波導路之芯材或包覆材。 The present invention relates to a chemically amplified positive-type photosensitive resin composition, a protective film formed therefrom, and an element with the protective film. Among them, in particular, a positive-type photosensitive resin composition for a protective film formed after exposure and development is provided, which has the characteristics of good development adhesion, good chemical resistance, and the like. This protective film is suitable for flattening film for thin film transistor (Thin Film Transistor; TFT) substrate of liquid crystal display element, organic EL display element, etc., interlayer insulating film or core material or cladding material of optical waveguide.
薄膜電晶體型液晶顯示元件或有機電致發光元件(organic electroluminescence device,有機EL元件)等顯示元件,通常包括層間絕緣膜或平坦化膜等絕緣膜。此種絕緣膜通常使用感放射線性組成物來形成。就圖案化性能的觀點而言,習知多使用利用萘醌二疊氮化物(naphthoquinone diazide)等酸產生劑的正型感放射線性 樹脂組成物(參照日本專利特開2001-354822號公報),做為此種感放射線性組成物,但近年來提出了多種感放射線性組成物。 A display element such as a thin film transistor liquid crystal display element or an organic electroluminescence device (organic electroluminescence device, organic EL element) generally includes an insulating film such as an interlayer insulating film or a planarizing film. Such an insulating film is usually formed using a radiation-sensitive composition. From the point of view of patterning performance, it is known that positive-type radiation-sensitive products using acid generators such as naphthoquinone diazide (naphthoquinone diazide) are often used. A resin composition (refer to Japanese Patent Application Laid-Open No. 2001-354822 ) is such a radiation-sensitive composition, but various radiation-sensitive compositions have been proposed in recent years.
舉例而言,提出了一種正型化學增幅材料,其目的在於:以較使用萘醌二疊氮化物等酸產生劑的前述正型感放射線性樹脂組成物具有更高的感度,來形成顯示元件用的硬化膜(參照日本專利特開2004-4669號公報)。所述正型化學增幅材料含有交聯劑、酸產生劑及酸解離性樹脂。酸解離性樹脂具有可利用酸的作用而解離的保護基,雖酸解離性樹脂本身不溶或者難溶於鹼性水溶液中,但通過利用酸的作用,使保護基解離而變得可溶於鹼性水溶液中。另外,也提出了含有具有縮醛結構及/或縮酮結構以及環氧基的樹脂及酸產生劑的正型感放射線性組成物(參照日本專利特開2004-264623號公報、日本專利特開2011-215596號公報以及日本專利特開2008-304902號公報)。 For example, a positive-type chemically amplified material has been proposed for the purpose of forming a display element with a higher sensitivity than the aforementioned positive-type radiation-sensitive resin composition using an acid generator such as naphthoquinonediazide. Cured film for use (refer to Japanese Patent Laid-Open No. 2004-4669). The positive chemical amplification material contains a crosslinking agent, an acid generator and an acid dissociative resin. Acid dissociative resins have protective groups that can be dissociated by the action of acids. Although acid dissociative resins themselves are insoluble or hardly soluble in alkaline aqueous solutions, they are dissociated by the action of acids and become soluble in alkalis. in aqueous solution. In addition, a positive radiation-sensitive composition containing a resin having an acetal structure and/or a ketal structure and an epoxy group and an acid generator has also been proposed (refer to Japanese Patent Laid-Open No. 2004-264623, Japanese Patent Laid-Open 2011-215596 and Japanese Patent Laid-Open No. 2008-304902).
這些感放射線性樹脂組成物中,除了高的放射線感度以外,還需要求即便長期保存,黏度也不會變化的保存穩定性,進而使這些感放射線性樹脂組成物形成的硬化膜,可達到不因顯影液等而膨潤的耐化性。進而,所述硬化膜形成的圖案也可達到:在顯影後,圖案與基板充分密合而難以剝離;硬化膜具有足夠的透明性;以及,即便在曝光後進行放置的情況下,圖案也與基板充分密合而難以剝離。 In these radiation-sensitive resin compositions, in addition to high radiation sensitivity, storage stability that does not change in viscosity even after long-term storage is required, so that the cured film formed by these radiation-sensitive resin compositions can be achieved. Chemical resistance to swelling due to developer, etc. Furthermore, the pattern formed by the cured film can also achieve: after development, the pattern is fully adhered to the substrate and is difficult to peel off; the cured film has sufficient transparency; and, even if placed after exposure, the pattern is also consistent with The substrates are sufficiently adhered to be difficult to peel off.
然而,目前的感光性樹脂組成物之顯影密著性、耐化性仍無法令業界所接受。 However, the development adhesion and chemical resistance of the current photosensitive resin composition are still not acceptable to the industry.
本發明的一個態樣在於提出一種化學增幅型正型感光性樹脂組成物。在一些實施例中,此化學增幅型正型感光性樹脂組成物可包含樹脂(A)、光酸產生劑(B)和溶劑(C),以下詳述之。 One aspect of the present invention is to provide a chemically amplified positive photosensitive resin composition. In some embodiments, the chemically amplified positive photosensitive resin composition may include a resin (A), a photoacid generator (B) and a solvent (C), which are described in detail below.
樹脂(A)Resin (A)
樹脂(A)是由混合物所共聚合而得。此混合物至少包括不飽和羧酸單體(a-1)、含矽烷基之不飽和化合物(a-2)以及含酸解離性基之單體(a-3)。 The resin (A) is obtained by copolymerizing the mixture. The mixture at least includes unsaturated carboxylic acid monomer (a-1), silyl group-containing unsaturated compound (a-2) and acid dissociative group-containing monomer (a-3).
不飽和羧酸單體(a-1)Unsaturated carboxylic acid monomer (a-1)
本發明之不飽和羧酸單體(a-1)係指包含羧酸基或羧酸酐結構及聚合結合用之不飽和鍵之化合物,其結構並無特別限制,可包括但不限於不飽和單羧酸化合物、不飽和二羧酸化合物、不飽和酸酐化合物、多環型不飽和羧酸化合物、多環型不飽和二羧酸化合物、多環型不飽和酸酐化合物。 The unsaturated carboxylic acid monomer (a-1) of the present invention refers to a compound containing a carboxylic acid group or a carboxylic acid anhydride structure and an unsaturated bond for polymerization. Its structure is not particularly limited, and may include but not limited to unsaturated mono Carboxylic acid compound, unsaturated dicarboxylic acid compound, unsaturated acid anhydride compound, polycyclic unsaturated carboxylic acid compound, polycyclic unsaturated dicarboxylic acid compound, polycyclic unsaturated acid anhydride compound.
前述不飽和單羧酸化合物之具體例如:(甲基)丙烯酸、丁烯酸、α-氯丙烯酸、乙基丙烯酸、肉桂酸、2-(甲基)丙烯醯乙氧基丁二酸酯、2-(甲基)丙烯醯乙氧基六氫化苯二甲酸酯、2-(甲基)丙烯醯乙氧基苯二甲酸酯、omega-羧基聚己內酯多元醇單丙烯酸酯(商品名為ARONIX M-5300,東亞合成製)。 Specific examples of the aforementioned unsaturated monocarboxylic acid compounds: (meth)acrylic acid, crotonic acid, α-chloroacrylic acid, ethacrylic acid, cinnamic acid, 2-(meth)acrylethoxysuccinate, 2 -(meth)acrylethoxyhexahydrophthalate, 2-(meth)acrylethoxyphthalate, omega-carboxypolycaprolactone polyol monoacrylate (trade name ARONIX M-5300, manufactured by Toagosei).
前述不飽和二羧酸化合物之具體例如:馬來 酸、富馬酸、甲基富馬酸、衣康酸、檸康酸等。於本發明之具體例中,不飽和二羧酸酐化合物為前述不飽和二羧酸化合物之酸酐化合物。 Specific examples of the aforementioned unsaturated dicarboxylic acid compounds: Malay acid, fumaric acid, methyl fumaric acid, itaconic acid, citraconic acid, etc. In a specific example of the present invention, the unsaturated dicarboxylic acid anhydride compound is an acid anhydride compound of the aforementioned unsaturated dicarboxylic acid compound.
前述多環型不飽和羧酸化合物之具體例如:5-羧基雙環[2.2.1]庚-2-烯、5-羧基-5-甲基雙環[2.2.1]庚-2-烯、5-羧基-5-乙基雙環[2.2.1]庚-2-烯、5-羧基-6-甲基雙環[2.2.1]庚-2-烯、5-羧基-6-乙基雙環[2.2.1]庚-2-烯。 Specific examples of the aforementioned polycyclic unsaturated carboxylic acid compounds: 5-carboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxybicyclo[2.2.1]hept-2-ene, Carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-ethylbicyclo[2.2. 1] Hept-2-ene.
前述多環型不飽和二羧酸化合物之具體例如:5,6-二羧酸二環[2.2.1]庚-2-烯。 A specific example of the aforementioned polycyclic unsaturated dicarboxylic acid compound is: 5,6-dicarboxylic acid bicyclo[2.2.1]hept-2-ene.
前述多環型不飽和二羧酸酐化合物為前述多環型不飽和二羧酸化合物之酸酐化合物。 The aforementioned polycyclic unsaturated dicarboxylic acid anhydride compound is an acid anhydride compound of the aforementioned polycyclic unsaturated dicarboxylic acid compound.
上述不飽和羧酸單體(a-1)之較佳具體例為丙烯酸、甲基丙烯酸、馬來酸酐、2-甲基丙烯醯乙氧基丁二酸酯、2-甲基丙烯醯基乙氧基六氫化苯二甲酸或其組合。 Preferred specific examples of the above-mentioned unsaturated carboxylic acid monomer (a-1) are acrylic acid, methacrylic acid, maleic anhydride, 2-methacrylethoxysuccinate, 2-methacrylylethyl Oxyhexahydrophthalic acid or combinations thereof.
上述不飽和羧酸單體(a-1)可單獨或混合複數種使用。基於合成樹脂(A)的混合物使用量100重量份,不飽和羧酸單體(a-1)之使用量為5重量份至50重量份;較佳為10重量份至45重量份;更佳為15重量份至45重量份。 The said unsaturated carboxylic acid monomer (a-1) can be used individually or in mixture of plural types. Based on 100 parts by weight of the mixture of synthetic resin (A), the usage of unsaturated carboxylic acid monomer (a-1) is 5 parts by weight to 50 parts by weight; preferably 10 parts by weight to 45 parts by weight; more preferably It is 15 parts by weight to 45 parts by weight.
含矽烷基之不飽和化合物(a-2)Unsaturated compounds containing silyl groups (a-2)
本發明之含矽烷基之不飽和化合物(a-2)具有如下示結構式(1-1)的結構:
於結構式(1-1)中,R1代表氫原子或甲基;R2及R3代表各自獨立的碳數為1至12之烷基、苯基、碳數為1至6之烷氧基或結構式(1-2)所示之基團;當R2及R3為複數,各個R2及R3為相同或不同;a代表1至6之整數;b代表1至150之整數;R4代表碳數為1至6之烷基或結構式(1-3)所示之基團。 In the structural formula (1-1), R 1 represents a hydrogen atom or a methyl group; R 2 and R 3 represent independent alkyl groups with 1 to 12 carbons, phenyl, and alkoxy groups with 1 to 6 carbons The group shown in group or structural formula (1-2); When R 2 and R 3 are plural, each R 2 and R 3 are the same or different; a represents an integer from 1 to 6; b represents an integer from 1 to 150 ; R 4 represents an alkyl group with a carbon number of 1 to 6 or a group represented by structural formula (1-3).
於結構式(1-2)中,R5、R6及R7代表各自獨立的碳數為1至12之烷基或苯基;當R6及R7為複數,各個R6及R7為相同或不同;c代表1至13之整數。 In the structural formula (1-2), R 5 , R 6 and R 7 represent independent alkyl or phenyl groups with 1 to 12 carbons; when R 6 and R 7 are plural, each R 6 and R 7 are the same or different; c represents an integer from 1 to 13.
於結構式(1-3)中,R8、R9及R10代表各自獨立的碳數為1至12之烷基或苯基。 In the structural formula (1-3), R 8 , R 9 and R 10 represent independent alkyl groups or phenyl groups with 1 to 12 carbon atoms.
所述碳數為1至12之烷基之具體例為甲基、乙 基、丙基、丁基、戊基、己基、庚基、辛基、壬基或癸基。 Specific examples of the alkyl group having a carbon number of 1 to 12 are methyl, ethyl, and propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl or decyl.
所述碳數為1至6之烷氧基之具體例為甲氧基、乙氧基、丙氧基或丁氧基。 Specific examples of the alkoxy group having 1 to 6 carbon atoms are methoxy, ethoxy, propoxy or butoxy.
所述結構式(1-1)所示之含矽烷基之不飽和化合物(a-2)包括烯丙基矽烷類(allylsilane)和甲基丙烯酸矽烷類(methacrylic silanes),其具體例為3-甲基丙烯醯氧基丙基三甲氧基矽烷(3-methacryloxypropyltrimethoxysilane)、3-甲基丙烯醯氧基丙基三乙氧基矽烷(3-methacryloxypropyltriethoxysilane)、3-甲基丙烯醯氧基丙基甲基二甲氧基矽烷(3-methacryloxypropylmethyldimethoxysilane)、3-甲基丙烯醯氧基丙基甲基二乙氧基矽烷(3-methacryloxypropylmethyldiethoxysilane)、由下述式(1-1-1)至(1-1-6)所示之化合物、由式(1-1-7)所示之(3-甲基丙烯醯氧基)丙基三(三甲基矽氧基)矽烷((3-methacryloyloxy)propyltris(trimethylsiloxy)silane;3MPTS)或FM-0711、FM-0721、FM-0725(Chisso Corporation製造)。 The silane group-containing unsaturated compound (a-2) represented by the structural formula (1-1) includes allylsilanes and methacrylic silanes, and its specific example is 3- Methacryloxypropyltrimethoxysilane (3-methacryloxypropyltrimethoxysilane), 3-methacryloxypropyltriethoxysilane (3-methacryloxypropyltriethoxysilane), 3-methacryloxypropyltrimethoxysilane 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane (3-methacryloxypropylmethyldiethoxysilane), from the following formula (1-1-1) to (1- The compound shown in 1-6), (3-methacryloyloxy) propyl tris (trimethylsilyloxy) silane ((3-methacryloyloxy) propyltris shown in formula (1-1-7) (trimethylsiloxy)silane; 3MPTS) or FM-0711, FM-0721, FM-0725 (manufactured by Chisso Corporation).
上述結構式(1-1)所示之含矽烷基之不飽和化合物(a-2)之較佳具體例為3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-甲基丙烯醯氧基丙基三乙氧基矽烷、由式(1-1-7)所示之(3-甲基丙烯醯氧基)丙基三(三甲基矽氧基)矽烷、FM-0711(Chisso Corporation製造)或其組合。 Preferred specific examples of the silyl group-containing unsaturated compound (a-2) represented by the above structural formula (1-1) are 3-methacryloxypropyl trimethoxysilane, 3-methacryl Oxypropyltriethoxysilane, (3-methacryloxy)propyltris(trimethylsiloxy)silane represented by formula (1-1-7), FM-0711 (Chisso Corporation) or a combination thereof.
上述結構式(1-1)所示之含矽烷基之不飽和化合物(a-2)可單獨或混合複數種使用。基於合成樹脂(A)的混合物使用量100重量份,結構式(1-1)所示之含矽烷基之不飽和化合物(a-2)之使用量為5重量份至50重量份;較佳為10重量份至45重量份;更佳為15重量份至45重量份。倘若合成樹脂(A)的混合物中未含有結構式(1-1)所示之含矽烷基之不飽和化合物(a-2),則由此化學增幅型正型感光性樹脂組成物形成的保護膜會有顯影密著性和耐化性不佳的問題。 The silyl group-containing unsaturated compound (a-2) represented by the above structural formula (1-1) can be used alone or in combination. Based on 100 parts by weight of the synthetic resin (A) mixture, the amount of the silyl group-containing unsaturated compound (a-2) represented by the structural formula (1-1) is 5 parts by weight to 50 parts by weight; preferably 10 parts by weight to 45 parts by weight; more preferably 15 parts by weight to 45 parts by weight. If the mixture of the synthetic resin (A) does not contain the silyl group-containing unsaturated compound (a-2) represented by the structural formula (1-1), the protection formed by the chemically amplified positive photosensitive resin composition The film has problems of development adhesion and poor chemical resistance.
含酸解離性基之單體(a-3)Acid dissociative group-containing monomer (a-3)
本發明之含酸解離性基之單體(a-3)具有如下結構式(2-1)所示之酸解離性基。 The acid-dissociating group-containing monomer (a-3) of the present invention has an acid-dissociating group represented by the following structural formula (2-1).
含酸解離性基之單體(a-3)的酸解離性基,在曝光時藉由自後述之光酸產生劑(B)產生的酸的作用而解離,並產生極性基,因此原本不溶或難溶於鹼水溶液的樹脂(A)變成對鹼水溶液具可溶性。 The acid-dissociable group of the acid-dissociable group-containing monomer (a-3) is dissociated by the action of the acid generated from the photoacid generator (B) described later at the time of exposure to generate a polar group, so it is originally insoluble Or the resin (A) which is poorly soluble in aqueous alkali solution becomes soluble in aqueous alkali solution.
所述含酸解離性基之單體(a-3)只要具有如結構式(2-1)的結構,則無特別限定。此含結構式(2-1)之酸解離性基之單體(a-3)可藉由酸而容易解離。在上述結構式(2-1)中,R11和R12各自獨立為氫原子、烷基、脂環式烴基或芳基,其中所述烷基、脂環式烴基或芳基所具有的氫原子的一部分或全部可被取代;而且,R11及R12不同時為氫原子;R13為烷基、脂環式烴基、芳烷基或者芳基;其中R13的烷基、脂環式烴基、芳烷基及芳基所具有的氫原子的一部分或全部可被取代;R11與R13可連結而形成環狀醚結構。例如:R11與R13可相互鍵結而與R11所鍵結的碳原子以及R13所鍵結的氧原子一起形成環狀醚結構。 The acid dissociative group-containing monomer (a-3) is not particularly limited as long as it has the structure of the structural formula (2-1). The monomer (a-3) containing the acid dissociative group of the structural formula (2-1) can be easily dissociated by acid. In the above structural formula (2-1), R 11 and R 12 are each independently a hydrogen atom, an alkyl group, an alicyclic hydrocarbon group or an aryl group, wherein the hydrogen contained in the alkyl group, alicyclic hydrocarbon group or aryl group is Part or all of the atoms can be substituted; and, R 11 and R 12 are not hydrogen atoms at the same time; R 13 is an alkyl group, an alicyclic hydrocarbon group, an aralkyl group or an aryl group; wherein R 13 is an alkyl group, an alicyclic group Part or all of the hydrogen atoms of the hydrocarbon group, aralkyl group, and aryl group may be substituted; R 11 and R 13 may be linked to form a cyclic ether structure. For example: R 11 and R 13 may be bonded to each other to form a cyclic ether structure together with the carbon atom to which R 11 is bonded and the oxygen atom to which R 13 is bonded.
上述R11及R12所表示的脂環式烴基例如可列舉碳數為3至20的脂環式烴基等。另外,此碳數為3至20的脂環式烴基可以是多環。上述碳數為3至20的脂環式烴基例如可列舉:環丙基、環戊基、環己基、環庚基、環辛基、冰片基、降冰片基、金剛烷基等。 Examples of the alicyclic hydrocarbon groups represented by R 11 and R 12 above include alicyclic hydrocarbon groups having 3 to 20 carbon atoms. In addition, this alicyclic hydrocarbon group having a carbon number of 3 to 20 may be polycyclic. Examples of the alicyclic hydrocarbon group having 3 to 20 carbon atoms include cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bornyl, norbornyl, adamantyl and the like.
上述R11及R12所表示的芳基例如可列舉碳數為6至14的芳基等。上述碳數為6至14的芳基可以是單環,也可以是單環連結而成的結構,還可以是縮合環。上述碳數為6至14的芳基例如可列舉苯基、萘基等。 The aryl group represented by the above-mentioned R 11 and R 12 includes, for example, an aryl group having 6 to 14 carbon atoms. The above-mentioned aryl group having 6 to 14 carbon atoms may be a single ring, may be a structure in which single rings are connected, or may be a condensed ring. Examples of the aryl group having 6 to 14 carbon atoms include phenyl, naphthyl and the like.
上述R11及R12所表示的可經取代的烷基、脂環式烴基以及芳基的取代基例如可列舉:鹵素原子、羥基、硝基、氰基、羧基、羰基、脂環式烴基(例如環丙基、環戊基、環己基、環庚基、環辛基、冰片基、降冰片基、金剛烷基等)、芳基(例如苯基、萘基等)、烷氧基(例如甲氧基、乙氧基、丙氧基、正丁氧基、戊氧基、己氧基、庚氧基、辛氧基等碳數為1至20的烷氧基等)、醯基(例如乙醯基、丙醯基、丁醯基、異丁醯基等碳數為2至20的醯基等)、醯氧基(例如乙醯氧基、丙醯氧基、丁醯氧基、第三丁醯氧基、第三戊醯氧基等碳數為2至10的醯氧基等)、烷氧基羰基(例如甲氧基羰基、乙氧基羰基、丙氧基羰基等碳數為2至20的烷氧基羰基)、鹵代烷基(例如甲基、乙基、正丙基、正丁基、正戊基、正己基、正辛基、正十二烷基、正十四烷基、正十八烷基等直鏈狀烷基,異丙基、異丁基、第三丁基、新戊基、2-己基、3-己基等分支狀烷基等烷基;環丙基、環丁基、環戊基、降冰片基、金剛烷基等脂環式烴基,將上述基團的一部分或者全部的氫原子經鹵素原子取代而得的基團)、羥基烷基(例如羥基甲基等)等。 The substituents of the optionally substituted alkyl, alicyclic hydrocarbon group, and aryl group represented by the above-mentioned R 11 and R 12 include, for example, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a carboxyl group, a carbonyl group, and an alicyclic hydrocarbon group ( Such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bornyl, norbornyl, adamantyl, etc.), aryl (such as phenyl, naphthyl, etc.), alkoxy (such as methoxy, ethoxy, propoxy, n-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy and other alkoxy groups with a carbon number of 1 to 20, etc.), acyl groups (such as Acyl, propionyl, butyryl, isobutyryl and other acyl groups with 2 to 20 carbon atoms, etc.), acyloxy (such as acetyloxy, propionyloxy, butyryloxy, tertiary butyryloxy acyloxy group with a carbon number of 2 to 10, such as the third pentyloxy group, etc.), an alkoxycarbonyl group (such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, etc., with a carbon number of 2 to 20 alkoxycarbonyl), haloalkyl (e.g. methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-octyl, n-dodecyl, n-tetradecyl, n-octadecyl Straight-chain alkyl such as alkyl, branched alkyl such as isopropyl, isobutyl, tertiary butyl, neopentyl, 2-hexyl, 3-hexyl, etc.; cyclopropyl, cyclobutyl, Cyclopentyl, norbornyl, adamantyl and other alicyclic hydrocarbon groups, groups obtained by substituting some or all of the hydrogen atoms of the above groups with halogen atoms), hydroxyalkyl groups (such as hydroxymethyl, etc.), etc. .
上述R13所表示的烷基、脂環式烴基、芳基可應用上述R11及R12所表示的各基團的說明。此外,上述烷基較佳為碳數為1至6的烷基,更佳為甲基、乙基以及正丙基。上述R13所表示的芳烷基可列舉:苄基、苯乙基、萘基甲基、萘基乙基等。 The alkyl group, alicyclic hydrocarbon group, and aryl group represented by the above-mentioned R 13 can apply the description of each group represented by the above-mentioned R 11 and R 12 . In addition, the above-mentioned alkyl group is preferably an alkyl group having 1 to 6 carbon atoms, more preferably methyl group, ethyl group and n-propyl group. The aralkyl group represented by R13 above includes benzyl, phenethyl, naphthylmethyl, naphthylethyl and the like.
上述R11與R13可相互鍵結而形成的環狀醚結 構,較佳為環員數3至20的環狀醚結構,更佳為環員數5至8的環狀醚結構,又更佳為四氫呋喃以及四氫吡喃。 The cyclic ether structure formed by the above-mentioned R 11 and R 13 being bonded to each other is preferably a cyclic ether structure with 3 to 20 ring members, more preferably a cyclic ether structure with 5 to 8 ring members, and even more Preferable are tetrahydrofuran and tetrahydropyran.
上述結構式(2-1)所表示的基團例如可列舉下述式所表示的基團等。 As for the group represented by the said structural formula (2-1), the group etc. which are represented by the following formula are mentioned, for example.
上述含酸解離性基之單體(a-3)例如可列舉:甲基丙烯酸1-乙氧基乙酯、甲基丙烯酸1-甲氧基乙酯、甲基丙烯酸1-正丁氧基乙酯、甲基丙烯酸1-異丁氧基乙酯、甲基丙烯酸1-第三丁氧基乙酯、甲基丙烯酸1-(2-氯乙氧基)乙酯、甲基丙烯酸1-(2-乙基己氧基)乙酯、甲基丙烯酸1-正丙氧基乙酯、甲基丙烯酸1-環己氧基乙酯、甲基丙烯酸1-(2-環己基乙氧基)乙酯、甲基丙烯酸1-苄氧基乙酯、甲基丙烯酸2-四氫吡喃基酯、2-四氫呋喃甲基丙烯酸酯(2-Tetrahydrofuranyl methacrylate)、丙烯酸1-乙氧基乙酯、丙烯酸1-甲氧基乙酯、丙烯酸1-正丁氧基乙酯、丙烯 酸1-異丁氧基乙酯、丙烯酸1-第三丁氧基乙酯、丙烯酸1-(2-氯乙氧基)乙酯、丙烯酸1-(2-乙基己氧基)乙酯、丙烯酸1-正丙氧基乙酯、丙烯酸1-環己氧基乙酯、丙烯酸1-(2-環己基乙氧基)乙酯、丙烯酸1-苄氧基乙酯、丙烯酸2-四氫吡喃基酯、5,6-二(1-甲氧基乙氧基羰基)-2-降冰片烯、5,6-二(1-(環己氧基)乙氧基羰基)-2-降冰片烯、5,6-二(1-(苄氧基)乙氧基羰基)-2-降冰片烯、對-1-乙氧基乙氧基苯乙烯或間-1-乙氧基乙氧基苯乙烯、對-1-甲氧基乙氧基苯乙烯或間-1-甲氧基乙氧基苯乙烯、對-1-正丁氧基乙氧基苯乙烯或間-1-正丁氧基乙氧基苯乙烯、對-1-異丁氧基乙氧基苯乙烯或間-1-異丁氧基乙氧基苯乙烯、對-1-(1,1-二甲基乙氧基)乙氧基苯乙烯或間-1-(1,1-二甲基乙氧基)乙氧基苯乙烯、對-1-(2-氯乙氧基)乙氧基苯乙烯或間-1-(2-氯乙氧基)乙氧基苯乙烯、對-1-(2-乙基己氧基)乙氧基苯乙烯或間-1-(2-乙基己氧基)乙氧基苯乙烯、對-1-正丙氧基乙氧基苯乙烯或間-1-正丙氧基乙氧基苯乙烯、對-1-環己氧基乙氧基苯乙烯或間-1-環己氧基乙氧基苯乙烯、對-1-(2-環己基乙氧基)乙氧基苯乙烯或間-1-(2-環己基乙氧基)乙氧基苯乙烯、對-1-苄氧基乙氧基苯乙烯或間-1-苄氧基乙氧基苯乙烯等。 Examples of the monomer (a-3) containing an acid dissociative group include: 1-ethoxyethyl methacrylate, 1-methoxyethyl methacrylate, 1-n-butoxyethyl methacrylate ester, 1-isobutoxyethyl methacrylate, 1-tert-butoxyethyl methacrylate, 1-(2-chloroethoxy)ethyl methacrylate, 1-(2 -Ethylhexyloxy)ethyl methacrylate, 1-n-propoxyethyl methacrylate, 1-cyclohexyloxyethyl methacrylate, 1-(2-cyclohexylethoxy)ethyl methacrylate , 1-benzyloxyethyl methacrylate, 2-tetrahydropyranyl methacrylate, 2-tetrahydrofuranyl methacrylate (2-Tetrahydrofuranyl methacrylate), 1-ethoxyethyl acrylate, 1- Methoxyethyl ester, 1-n-butoxyethyl acrylate, propylene 1-isobutoxyethyl acrylate, 1-tert-butoxyethyl acrylate, 1-(2-chloroethoxy)ethyl acrylate, 1-(2-ethylhexyloxy)ethyl acrylate, 1-n-propoxyethyl acrylate, 1-cyclohexyloxyethyl acrylate, 1-(2-cyclohexylethoxy)ethyl acrylate, 1-benzyloxyethyl acrylate, 2-tetrahydropyridine acrylate Nyl ester, 5,6-bis(1-methoxyethoxycarbonyl)-2-norbornene, 5,6-bis(1-(cyclohexyloxy)ethoxycarbonyl)-2-norbornene Bornene, 5,6-bis(1-(benzyloxy)ethoxycarbonyl)-2-norbornene, p-1-ethoxyethoxystyrene or m-1-ethoxyethoxy p-1-methoxyethoxystyrene or m-1-methoxyethoxystyrene, p-1-n-butoxyethoxystyrene or m-1-n-butyl Oxyethoxystyrene, p-1-isobutoxyethoxystyrene or m-1-isobutoxyethoxystyrene, p-1-(1,1-dimethylethoxy base) ethoxystyrene or m-1-(1,1-dimethylethoxy)ethoxystyrene, p-1-(2-chloroethoxy)ethoxystyrene or m- 1-(2-chloroethoxy)ethoxystyrene, p-1-(2-ethylhexyloxy)ethoxystyrene or m-1-(2-ethylhexyloxy)ethoxy Styrene, p-1-n-propoxyethoxystyrene or m-1-n-propoxyethoxystyrene, p-1-cyclohexyloxyethoxystyrene or m-1- Cyclohexyloxyethoxystyrene, p-1-(2-cyclohexylethoxy)ethoxystyrene or m-1-(2-cyclohexylethoxy)ethoxystyrene, p- 1-benzyloxyethoxystyrene or m-1-benzyloxyethoxystyrene, etc.
含酸解離性基之單體(a-3)較佳為甲基丙烯酸1-乙氧基乙酯、甲基丙烯酸1-正丁氧基乙酯、甲基丙烯酸2-四氫吡喃基酯、甲基丙烯酸1-苄氧基乙酯、甲基丙烯酸1-環己氧基乙酯、2-四氫呋喃甲基丙烯酸酯,更佳為甲基丙烯酸2-四氫吡喃基酯和2-四氫呋喃甲基丙烯酸酯。 The acid dissociative group-containing monomer (a-3) is preferably 1-ethoxyethyl methacrylate, 1-n-butoxyethyl methacrylate, 2-tetrahydropyranyl methacrylate , 1-benzyloxyethyl methacrylate, 1-cyclohexyloxyethyl methacrylate, 2-tetrahydrofuran methacrylate, more preferably 2-tetrahydropyranyl methacrylate and 2-tetrahydrofuran Methacrylate.
基於所述混合物的使用量為100重量份,所述單體(a-3)的使用量為5重量份至90重量份,較佳為10重量份至80重量份,更佳為15重量份至70重量份。若無使用單體(a-3)時,會有顯影密著性不佳、耐化性不佳的問題。 Based on 100 parts by weight of the mixture, the monomer (a-3) is used in an amount of 5 parts by weight to 90 parts by weight, preferably 10 parts by weight to 80 parts by weight, more preferably 15 parts by weight to 70 parts by weight. If the monomer (a-3) is not used, there are problems of poor image development adhesion and poor chemical resistance.
含環氧基之不飽和單體(a-4)Unsaturated monomer containing epoxy group (a-4)
在一些實施例中,所述混合物可進一步包括含環氧基之不飽和單體(a-4)。 In some embodiments, the mixture may further include an epoxy group-containing unsaturated monomer (a-4).
所述含環氧基之不飽和單體(a-4)可包括但不限於含環氧基之(甲基)丙烯酸酯化合物、含環氧基之α-烷基丙烯酸酯化合物、環氧丙醚化合物、如結構式(3-1)所示的具有氧雜環丁烷基之乙烯性不飽和單體,及上述之任意組合。 The epoxy-containing unsaturated monomer (a-4) may include, but not limited to, epoxy-containing (meth)acrylate compounds, epoxy-containing α-alkyl acrylate compounds, epoxypropylene An ether compound, an ethylenically unsaturated monomer having an oxetanyl group represented by structural formula (3-1), and any combination of the above.
於結構式(3-1)中,R14代表氫原子或碳數為1至4之烷基;R15代表氫原子或碳數為1至4之烷基;R16、R17、R18及R19分別獨立地代表氫原子、氟原子、苯基、碳數為1至4之烷基或碳數為1至4之全氟烷基;且a代表1至6之整數。 In the structural formula (3-1), R 14 represents a hydrogen atom or an alkyl group with a carbon number of 1 to 4; R 15 represents a hydrogen atom or an alkyl group with a carbon number of 1 to 4; R 16 , R 17 , R 18 and R 19 each independently represent a hydrogen atom, a fluorine atom, a phenyl group, an alkyl group with a carbon number of 1 to 4, or a perfluoroalkyl group with a carbon number of 1 to 4; and a represents an integer of 1 to 6.
前述含環氧基之(甲基)丙烯酸酯化合物之具體例如:(甲基)丙烯酸環氧丙酯、(甲基)丙烯酸2-甲基環氧丙酯、(甲基)丙烯酸3,4-環氧丁酯、(甲基)丙烯酸6,7-環氧庚酯、(甲基)丙烯酸3,4-環氧環己酯、(甲基)丙烯酸3,4-環氧 環己基甲酯。 Specific examples of the aforementioned epoxy group-containing (meth)acrylate compounds: glycidyl (meth)acrylate, 2-methylglycidyl (meth)acrylate, 3,4-(meth)acrylate Epoxybutyl, 6,7-epoxyheptyl (meth)acrylate, 3,4-epoxycyclohexyl (meth)acrylate, 3,4-epoxy(meth)acrylate Cyclohexyl methyl ester.
前述含環氧基之α-烷基丙烯酸酯化合物之具體例如:α-乙基丙烯酸環氧丙酯、α-正丙基丙烯酸環氧丙酯、α-正丁基丙烯酸環氧丙酯、α-乙基丙烯酸6,7-環氧庚酯。 Specific examples of the aforementioned α-alkyl acrylate compounds containing epoxy groups: α-glycidyl ethacrylate, α-glycidyl propyl acrylate, α-glycidyl butyl acrylate, α - 6,7-epoxyheptyl ethacrylate.
前述環氧丙醚化合物之具體例如:鄰-乙烯基苯甲基環氧丙醚(o-vinylbenzylglycidylether)、間-乙烯基苯甲基環氧丙醚(m-vinylbenzylglycidylether)、對-乙烯基苯甲基環氧丙醚(p-vinylbenzylglycidylether)。 Specific examples of the aforementioned glycidyl ether compounds: o-vinylbenzylglycidylether (o-vinylbenzylglycidylether), m-vinylbenzylglycidylether (m-vinylbenzylglycidylether), p-vinylbenzylglycidylether Glycidyl ether (p-vinylbenzylglycidylether).
前述如結構式(3-1)所示的具有氧雜環丁烷基之乙烯性不飽和單體之具體例可包含但不限於甲基丙烯酸酯類化合物、丙烯酸酯類化合物或具有如下式(3-2)至式(3-5)所示之結構的不飽和單體。 Specific examples of the above-mentioned ethylenically unsaturated monomers having an oxetane group as shown in structural formula (3-1) may include but not limited to methacrylate compounds, acrylate compounds or have the following formula ( 3-2) Unsaturated monomers having structures represented by formula (3-5).
前述之甲基丙烯酸酯類化合物可包含但不限於3-(甲基丙烯醯氧基甲基)氧雜環丁烷[3-(methacryloyloxymethyl)oxetane;OXMA]、3-(甲基丙烯醯氧基甲基)-3-乙基氧雜環丁烷[3-(methacryloyloxymethyl)-3-ethyloxetane;EOXMA]、3-(甲基丙烯醯氧基甲基)-3-甲基氧雜環丁烷[3-(methacryloyloxymethyl)-3-methyloxetane;MOXMA]、3-(甲基丙烯醯氧基甲基)-2-甲基氧雜環丁烷、3-(甲基丙烯醯氧基甲基)-2-三氟甲基氧雜環丁烷、3-(甲基丙烯醯氧基甲基)-2-五氟乙基氧雜環丁烷、3-(甲基丙烯醯氧基甲基)-2-苯基氧雜環丁烷、3-(甲基丙烯醯氧基甲基)-2,2-二氟氧雜環丁烷、3-(甲基丙烯醯氧基甲基)-2,2,4- 三氟氧雜環丁烷、3-(甲基丙烯醯氧基甲基)-2,2,4,4-四氟氧雜環丁烷、3-(甲基丙烯醯氧基乙基)氧雜環丁烷、3-(甲基丙烯醯氧基乙基)-3-乙基氧雜環丁烷、2-乙基-3-(甲基丙烯醯氧基乙基)氧雜環丁烷、3-(甲基丙烯醯氧基乙基)-2-三氟甲基氧雜環丁烷、3-(甲基丙烯醯氧基乙基)-2-五氟乙基氧雜環丁烷、3-(甲基丙烯醯氧基乙基)-2-苯基氧雜環丁烷、2,2-二氟-3-(甲基丙烯醯氧基乙基)氧雜環丁烷、3-(甲基丙烯醯氧基乙基)-2,2,4-三氟氧雜環丁烷或3-(甲基丙烯醯氧基乙基)-2,2,4,4-四氟氧雜環丁烷等之化合物。 The aforementioned methacrylate compounds may include, but are not limited to, 3-(methacryloxymethyl)oxetane [3-(methacryloyloxymethyl)oxetane; OXMA], 3-(methacryloxymethyl) Methyl)-3-ethyloxetane [3-(methacryloyloxymethyl)-3-ethyloxetane; EOXMA], 3-(methacryloyloxymethyl)-3-methyloxetane [ 3-(methacryloyloxymethyl)-3-methyloxetane; MOXMA], 3-(methacryloxymethyl)-2-methyloxetane, 3-(methacryloxymethyl)-2 -Trifluoromethyloxetane, 3-(methacryloxymethyl)-2-pentafluoroethyloxetane, 3-(methacryloxymethyl)-2 -Phenyloxetane, 3-(methacryloxymethyl)-2,2-difluorooxetane, 3-(methacryloxymethyl)-2,2 ,4- Trifluorooxetane, 3-(methacryloxymethyl)-2,2,4,4-tetrafluorooxetane, 3-(methacryloxyethyl)oxy Hetetane, 3-(methacryloxyethyl)-3-ethyloxetane, 2-ethyl-3-(methacryloxyethyl)oxetane , 3-(methacryloxyethyl)-2-trifluoromethyloxetane, 3-(methacryloxyethyl)-2-pentafluoroethyloxetane , 3-(methacryloxyethyl)-2-phenyloxetane, 2,2-difluoro-3-(methacryloxyethyl)oxetane, 3 -(methacryloxyethyl)-2,2,4-trifluorooxetane or 3-(methacryloxyethyl)-2,2,4,4-tetrafluorooxetane Compounds such as heterocyclobutane.
上述之丙烯酸酯類化合物可包含但不限於3-(丙烯醯氧基甲基)氧雜環丁烷、3-(丙烯醯氧基甲基)-3-乙基氧雜環丁烷、3-(丙烯醯氧基甲基)-3-甲基氧雜環丁烷、3-(丙烯醯氧基甲基)-2-甲基氧雜環丁烷、3-(丙烯醯氧基甲基)-2-三氟甲基氧雜環丁烷、3-(丙烯醯氧基甲基)-2-五氟乙基氧雜環丁烷、3-(丙烯醯氧基甲基)-2-苯基氧雜環丁烷、3-(丙烯醯氧基甲基)-2,2-二氟氧雜環丁烷、3-(丙烯醯氧基甲基)-2,2,4-三氟氧雜環丁烷、3-(丙烯醯氧基甲基)-2,2,4,4-四氟氧雜環丁烷、3-(丙烯醯氧基乙基)氧雜環丁烷、3-(丙烯醯氧基乙基)-3-乙基氧雜環丁烷、2-乙基-3-(丙烯醯氧基乙基)氧雜環丁烷、3-(丙烯醯氧基乙基)-2-三氟甲基氧雜環丁烷、3-(丙烯醯氧基乙基)-2-五氟乙基氧雜環丁烷、3-(丙烯醯氧基乙基)-2-苯基氧雜環丁烷、2,2-二氟-3-(丙烯醯氧基乙基)氧雜環丁烷、3-(丙烯醯氧基乙基)-2,2,4-三氟氧雜環丁烷或3-(丙烯醯氧基乙 基)-2,2,4,4-四氟氧雜環丁烷等之化合物。 The above-mentioned acrylate compounds may include but not limited to 3-(acryloxymethyl)oxetane, 3-(acryloxymethyl)-3-ethyloxetane, 3- (Acryloxymethyl)-3-methyloxetane, 3-(Acryloxymethyl)-2-methyloxetane, 3-(Acryloxymethyl) -2-trifluoromethyloxetane, 3-(acryloxymethyl)-2-pentafluoroethyloxetane, 3-(acryloxymethyl)-2-benzene 3-(acryloxymethyl)-2,2-difluorooxetane, 3-(acryloxymethyl)-2,2,4-trifluorooxetane Heteretane, 3-(acryloxymethyl)-2,2,4,4-tetrafluorooxetane, 3-(acryloxyethyl)oxetane, 3- (Acryloxyethyl)-3-ethyloxetane, 2-ethyl-3-(acryloxyethyl)oxetane, 3-(acryloxyethyl) -2-trifluoromethyloxetane, 3-(acryloxyethyl)-2-pentafluoroethyloxetane, 3-(acryloxyethyl)-2-benzene oxetane, 2,2-difluoro-3-(acryloxyethyl)oxetane, 3-(acryloxyethyl)-2,2,4-trifluorooxy heterocyclobutane or 3-(acryloxyethyl base)-2,2,4,4-tetrafluorooxetane and other compounds.
前述具有如式(3-2)至式(3-5)所示之結構的不飽和單體如下所示。 The aforementioned unsaturated monomers having structures represented by formula (3-2) to formula (3-5) are shown below.
在一些實施例中,所述含環氧基的不飽和單體(a-4)可更包含其他具有氧雜環丁烷基之乙烯性不飽和單體,如:3-甲基-3-(乙烯氧基甲基)氧雜環丁烷 [3-methyl-3-(vinyloxymethyl)oxetane;MOXV]、3-乙基-3-(乙烯氧基甲基)氧雜環丁烷[3-ethyl-3-(vinyloxymethyl)oxetane;EOXV]、3-丙基-3-(乙烯氧基甲基)氧雜環丁烷、3-甲基-3-(2-乙烯氧基乙基)氧雜環丁烷、3-乙基-3-(2-乙烯氧基乙基)氧雜環丁烷、3-丙基-3-(2-乙烯氧基乙基)氧雜環丁烷、3-甲基-3-(3-乙烯氧基丙基)氧雜環丁烷、3-乙基-3-(3-乙烯氧基丙基)氧雜環丁烷、3-丙基-3-(3-乙烯氧基丙基)氧雜環丁烷、3-甲基-3-(3-乙烯氧基丁基)氧雜環丁烷、3-乙基-3-(3-乙烯氧基丁基)氧雜環丁烷、3-丙基-3-(3-乙烯氧基丁基)氧雜環丁烷、乙二醇[(3-乙基-3-氧雜環丁基)甲基]乙烯基醚、丙二醇[(3-乙基-3-氧雜環丁基)甲基]乙烯基醚或3,3-雙[(乙烯氧基)甲基]氧雜環丁烷等之具有氧雜環丁烷基的乙烯基醚化合物。 In some embodiments, the epoxy-containing unsaturated monomer (a-4) may further include other ethylenically unsaturated monomers having an oxetanyl group, such as: 3-methyl-3- (Ethyleneoxymethyl)oxetane [3-methyl-3-(vinyloxymethyl)oxetane; MOXV], 3-ethyl-3-(vinyloxymethyl)oxetane [3-ethyl-3-(vinyloxymethyl)oxetane; EOXV], 3 -Propyl-3-(vinyloxymethyl)oxetane, 3-methyl-3-(2-vinyloxyethyl)oxetane, 3-ethyl-3-(2 -vinyloxyethyl)oxetane, 3-propyl-3-(2-vinyloxyethyl)oxetane, 3-methyl-3-(3-vinyloxypropyl ) oxetane, 3-ethyl-3-(3-vinyloxypropyl) oxetane, 3-propyl-3-(3-vinyloxypropyl) oxetane , 3-methyl-3-(3-vinyloxybutyl) oxetane, 3-ethyl-3-(3-vinyloxybutyl) oxetane, 3-propyl- 3-(3-vinyloxybutyl) oxetane, ethylene glycol [(3-ethyl-3-oxetanyl) methyl] vinyl ether, propylene glycol [(3-ethyl- Vinyl ether compounds having an oxetanyl group such as 3-oxetanyl)methyl]vinyl ether or 3,3-bis[(vinyloxy)methyl]oxetane.
基於所述混合物的使用量為100重量份,所述含環氧基的不飽和單體(a-4)的使用量為5重量份至80重量份,較佳為10重量份至70重量份,更佳為15重量份至65重量份。若使用含環氧基的不飽和單體(a-4),會有顯影密著性佳之優點。 Based on the usage amount of the mixture being 100 parts by weight, the usage amount of the epoxy group-containing unsaturated monomer (a-4) is 5 parts by weight to 80 parts by weight, preferably 10 parts by weight to 70 parts by weight , More preferably 15 parts by weight to 65 parts by weight. If the epoxy-group-containing unsaturated monomer (a-4) is used, it will have the advantage of good developing adhesiveness.
在一些實施例中,較佳的,基於所述混合物的使用量為100重量份,如結構式(3-1)所示的具有氧雜環丁烷基之乙烯性不飽和單體的使用量為5重量份至80重量份,較佳為10重量份至70重量份,更佳為15重量份至65重量份,其可再進一步改善顯影密著性。 In some embodiments, preferably, based on 100 parts by weight of the mixture, the usage amount of the ethylenically unsaturated monomer having an oxetanyl group shown in structural formula (3-1) It is 5 parts by weight to 80 parts by weight, preferably 10 parts by weight to 70 parts by weight, more preferably 15 parts by weight to 65 parts by weight, which can further improve the developing adhesiveness.
其他不飽和單體(a-5)Other unsaturated monomers (a-5)
所述用於形成樹脂(A)的混合物中,可更包含其他不飽和單體(a-5)。在一些實施例中,其他不飽和單體(a-5)可包括但不限於(甲基)丙烯酸烷基酯、(甲基)丙烯酸脂環族酯、(甲基)丙烯酸芳基酯、不飽和二羧酸二酯、(甲基)丙烯酸羥烷酯、(甲基)丙烯酸酯之聚醚、芳香乙烯化合物及前述以外之其他不飽和化合物。 The mixture for forming the resin (A) may further include other unsaturated monomers (a-5). In some embodiments, other unsaturated monomers (a-5) may include, but are not limited to, alkyl (meth)acrylates, cycloaliphatic (meth)acrylates, aryl (meth)acrylates, Saturated dicarboxylic acid diesters, hydroxyalkyl (meth)acrylates, polyethers of (meth)acrylates, aromatic vinyl compounds, and other unsaturated compounds other than those mentioned above.
前述(甲基)丙烯酸烷基酯之具體例如:(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸正丙酯、(甲基)丙烯酸異丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸二級丁酯、(甲基)丙烯酸三級丁酯。 Specific examples of the aforementioned alkyl (meth)acrylates: methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, (meth)acrylate ) n-butyl acrylate, isobutyl (meth)acrylate, secondary butyl (meth)acrylate, tertiary butyl (meth)acrylate.
前述(甲基)丙烯酸脂環族酯之具體例如:(甲基)丙烯酸環己酯、(甲基)丙烯酸-2-甲基環己酯、三環[5.2.1.02,6]癸-8-基(甲基)丙烯酸酯(或稱為(甲基)丙烯酸雙環戊酯)、(甲基)丙烯酸二環戊氧基乙酯、(甲基)丙烯酸異冰片酯、(甲基)丙烯酸四氫呋喃酯。 Specific examples of the aforementioned cycloaliphatic (meth)acrylates: cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decane-8 -yl (meth)acrylate (or dicyclopentyl (meth)acrylate), dicyclopentyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, tetrahydrofuran (meth)acrylate ester.
前述(甲基)丙烯酸芳基酯之具體例如:(甲基)丙烯酸苯基酯、(甲基)丙烯酸苯甲酯。 Specific examples of the aforementioned aryl (meth)acrylate: phenyl (meth)acrylate, benzyl (meth)acrylate.
前述不飽和二羧酸二酯之具體例如馬來酸二乙酯、富馬酸二乙酯、衣康酸二乙酯。 Specific examples of the aforementioned unsaturated dicarboxylic acid diesters include diethyl maleate, diethyl fumarate, and diethyl itaconate.
前述(甲基)丙烯酸羥烷酯之具體例如:(甲基)丙烯酸-2-羥基乙酯、(甲基)丙烯酸-2-羥基丙酯。 Specific examples of the aforementioned hydroxyalkyl (meth)acrylates include 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate.
前述(甲基)丙烯酸酯之聚醚之具體例如:聚乙二醇單(甲基)丙烯酸酯、聚丙二醇單(甲基)丙烯酸酯。 Specific examples of the aforementioned polyethers of (meth)acrylates include polyethylene glycol mono(meth)acrylate and polypropylene glycol mono(meth)acrylate.
前述芳香乙烯化合物之具體例如:苯乙烯、α-甲基苯乙烯、間-甲基苯乙烯,對-甲基苯乙烯、對-甲氧基苯乙烯。 Specific examples of the aforementioned aromatic vinyl compounds include styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, and p-methoxystyrene.
前述以外之其他不飽和化合物之具體例如:丙烯腈、甲基丙烯腈、氯乙烯、偏二氯乙烯、丙烯醯胺、甲基丙烯醯胺、乙烯乙酯、1,3-丁二烯、異戊二烯、2,3-二甲基1,3-丁二烯、N-環己基馬來醯亞胺、N-苯基馬來醯亞胺、N-芐基馬來醯亞胺,N-丁二醯亞胺基-3-馬來醯亞胺苯甲酸酯、N-丁二醯亞胺基-4-馬來醯亞胺丁酸酯、N-丁二醯亞胺基-6-馬來醯亞胺己酸酯、N-丁二醯亞胺基-3-馬來醯亞胺丙酸酯、N-(9-吖啶基)馬來醯亞胺。 Specific examples of other unsaturated compounds other than the above: acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, ethylene ethyl ester, 1,3-butadiene, iso Pentadiene, 2,3-dimethyl-1,3-butadiene, N-cyclohexylmaleimide, N-phenylmaleimide, N-benzylmaleimide, N -Succimidyl-3-maleimide benzoate, N-succimidyl-4-maleimide butyrate, N-succimidyl-6 -maleimide caproate, N-succimidyl-3-maleimide propionate, N-(9-acridinyl)maleimide.
基於所述混合物的使用量為100重量份,所述其他不飽和單體(a-5)的使用量為0重量份至90重量份,較佳為5重量份至85重量份,更佳為5重量份至80重量份。 Based on the usage amount of the mixture being 100 parts by weight, the usage amount of the other unsaturated monomer (a-5) is 0 parts by weight to 90 parts by weight, preferably 5 parts by weight to 85 parts by weight, more preferably 5 parts by weight to 80 parts by weight.
製備樹脂(A)Preparation of Resin (A)
本發明之樹脂(A)在製造時所使用溶劑可包括但不限於醇、醚、二醇醚、乙二醇烷基醚乙酸醋酸酯、二乙二醇、二丙二醇、丙二醇單烷基醚、丙二醇烷基醚乙酸醋酸酯、丙二醇烷基醚丙酸酯、芳香烴、酮、酯。 The solvent used in the manufacture of resin (A) of the present invention may include but not limited to alcohol, ether, glycol ether, ethylene glycol alkyl ether acetate acetate, diethylene glycol, dipropylene glycol, propylene glycol monoalkyl ether, Propylene Glycol Alkyl Ether Acetate, Propylene Glycol Alkyl Ether Propionate, Aromatic Hydrocarbon, Ketone, Ester.
前述醇之具體例如:甲醇、乙醇、苯甲醇、2-苯乙醇、3-苯基-1-丙醇。前述醚之具體例如:四氫呋喃。前述二醇醚之具體例如:乙二醇單丙醚、乙二醇單甲醚、乙二醇單乙醚。前述乙二醇烷基醚醋酸酯之具體例如:乙二醇丁醚醋酸酯、乙二醇乙醚醋酸酯、乙二醇甲醚醋酸酯。前述 二乙二醇之具體例如:二乙二醇單甲醚、二乙二醇單乙醚、二乙二醇單丁醚、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇甲乙醚。前述二丙二醇之具體例如:二丙二醇單甲醚、二丙二醇單乙醚、二丙二醇二甲醚、二丙二醇二乙醚、二丙二醇甲乙醚。前述丙二醇單烷基醚之具體例如:丙二醇單甲醚、丙二醇單乙醚、丙二醇單丙醚、丙二醇單丁醚。前述丙二醇烷基醚醋酸酯之具體例如:丙二醇甲醚醋酸酯、丙二醇乙醚醋酸酯、丙二醇丙醚醋酸酯、丙二醇丁醚醋酸酯。前述丙二醇烷基醚丙酸酯之具體例如:丙二醇甲醚丙酸酯、丙二醇乙醚丙酸酯、丙二醇丙醚丙酸酯、丙二醇丁醚丙酸酯。前述芳香烴之具體例如:甲苯、二甲苯。前述酮之具體例如:甲乙酮、環己酮、二丙酮醇。前述酯之具體例如:乙酸甲酯、乙酸乙酯、乙酸丙酯、乙酸丁酯、2-羥基丙酸乙酯、2-羥基-2-甲基丙酸甲酯、2-羥基-2-甲基丙酸乙酯、羥乙酸甲酯、羥乙酸乙酯、羥乙酸丁酯、乳酸甲酯、乳酸丙酯、乳酸丁酯、3-羥基丙酸甲酯、3-羥基丙酸乙酯、3-羥基丙酸丙酯、3-羥基丙酸丁酯、2-羥基-3-甲基丁酸甲酯、甲氧基乙酸甲酯、甲氧基乙酸乙酯、甲氧基乙酸丁酯、乙氧基乙酸甲酯、乙氧基乙酸乙酯、乙氧基乙酸丙酯、乙氧基乙酸丁酯、丙氧基乙酸甲酯、丙氧基乙酸乙酯、丙氧基乙酸丙酯、丙氧基乙酸丁酯、丁氧基乙酸甲酯、丁氧基乙酸乙酯、丁氧基乙酸丙酯、丁氧基乙酸丁酯、3-甲氧基丁基乙酸酯、2-甲氧基丙酸甲酯、2-甲氧基丙酸乙酯、2-甲氧基丙酸丙酯、2-甲氧基丙酸丁酯、2-乙氧基丙酸甲酯、2-乙氧基丙酸乙酯、2-乙氧基丙 酸丙酯、2-乙氧基丙酸丁酯、2-丁氧基丙酸甲酯、2-丁氧基丙酸甲酯、2-丁氧基丙酸乙酯、2-丁氧基丙酸丙酯、2-丁氧基丙酸丁酯、3-甲氧基丙酸甲酯、3-甲氧基丙酸乙酯、3-甲氧基丙酸丙酯、3-甲氧基丙酸丁酯、3-乙氧基丙酸甲酯、3-乙氧基丙酸乙酯、3-乙氧基丙酸丙酯、3-乙氧基丙酸丁酯、3-丙氧基丙酸甲酯、3-丙氧基丙酸乙酯、3-丙氧基丙酸丙酯、3-丙氧基丙酸丁酯、3-丁氧基丙酸甲酯、3-丁氧基丙酸乙酯、3-丁氧基丙酸丙酯、3-丁氧基丙酸丁酯。 Specific examples of the aforementioned alcohols include methanol, ethanol, benzyl alcohol, 2-phenylethyl alcohol, and 3-phenyl-1-propanol. A specific example of the aforementioned ether is tetrahydrofuran. Specific examples of the aforementioned glycol ethers include ethylene glycol monopropyl ether, ethylene glycol monomethyl ether, and ethylene glycol monoethyl ether. Specific examples of the aforementioned ethylene glycol alkyl ether acetates include ethylene glycol butyl ether acetate, ethylene glycol ethyl ether acetate, and ethylene glycol methyl ether acetate. aforementioned Specific examples of diethylene glycol: diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol Methyl ether. Specific examples of the aforementioned dipropylene glycol include dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, and dipropylene glycol methyl ethyl ether. Specific examples of the aforementioned propylene glycol monoalkyl ethers include propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, and propylene glycol monobutyl ether. Specific examples of the aforementioned propylene glycol alkyl ether acetates include propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate, and propylene glycol butyl ether acetate. Specific examples of the aforementioned propylene glycol alkyl ether propionate: propylene glycol methyl ether propionate, propylene glycol ethyl ether propionate, propylene glycol propyl ether propionate, and propylene glycol butyl ether propionate. Specific examples of the aforementioned aromatic hydrocarbons include toluene and xylene. Specific examples of the aforementioned ketones include methyl ethyl ketone, cyclohexanone, and diacetone alcohol. Specific examples of the aforementioned esters: methyl acetate, ethyl acetate, propyl acetate, butyl acetate, ethyl 2-hydroxypropionate, methyl 2-hydroxy-2-methylpropionate, 2-hydroxy-2-methyl Ethyl glycolate, methyl glycolate, ethyl glycolate, butyl glycolate, methyl lactate, propyl lactate, butyl lactate, methyl 3-hydroxypropionate, ethyl 3-hydroxypropionate, 3 - Propyl hydroxypropionate, butyl 3-hydroxypropionate, methyl 2-hydroxy-3-methylbutyrate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, ethyl Methyl oxyacetate, ethyl ethoxy acetate, propyl ethoxy acetate, butyl ethoxy acetate, methyl propoxy acetate, ethyl propoxy acetate, propyl propoxy acetate, propoxy Butyl acetate, butoxy methyl acetate, butoxy ethyl acetate, butoxy propyl acetate, butoxy butyl acetate, 3-methoxybutyl acetate, 2-methoxypropane Methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, butyl 2-methoxypropionate, methyl 2-ethoxypropionate, 2-ethoxypropionate ethyl acetate, 2-ethoxypropane Propyl 2-ethoxypropionate, butyl 2-butoxypropionate, methyl 2-butoxypropionate, methyl 2-butoxypropionate, ethyl 2-butoxypropionate, 2-butoxypropionate Propyl propionate, butyl 2-butoxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionate, 3-methoxypropionate Butyl 3-ethoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, propyl 3-ethoxypropionate, butyl 3-ethoxypropionate, 3-propoxypropionate Methyl 3-propoxypropionate, ethyl 3-propoxypropionate, propyl 3-propoxypropionate, butyl 3-propoxypropionate, methyl 3-butoxypropionate, 3-butoxypropionate Ethyl 3-butoxypropionate, propyl 3-butoxypropionate, butyl 3-butoxypropionate.
本發明之樹脂(A)在製造時所使用溶劑之較佳具體例為二乙二醇二甲醚、丙二醇甲醚醋酸酯。上述溶劑可單獨或混合複數種使用。 Preferred specific examples of the solvent used in the manufacture of the resin (A) of the present invention are diethylene glycol dimethyl ether and propylene glycol methyl ether acetate. The above-mentioned solvents can be used alone or in combination.
本發明之樹脂(A)在製造時所使用之聚合起始劑,其具體例為偶氮化合物或過氧化物。前述偶氮化合物之具體例如:2,2'-偶氮二異丁腈、2,2'-偶氮二(2,4-二甲基戊腈)、2,2'-偶氮二(4-甲氧基-2,4-二甲基戊腈)、2,2'-偶氮二(2-甲基丁腈)、4,4'-偶氮二(4-氰基戊酸)、2,2'-偶氮二(二甲基-2-甲基丙酸酯)。前述過氧化物之具體例如:過氧化二苯甲醯、過氧化二月桂醯(dilauroyl peroxide)、第三丁基過氧化新戊酸酯(tert-butyl peroxypivalate)、1,1-二(第三丁基過氧化)環己烷(1,1-di(tert-butylperoxy)cyclohexane)、過氧化氫。上述聚合起始劑可單獨或混合複數種使用。 The specific example of the polymerization initiator used in the production of the resin (A) of the present invention is an azo compound or a peroxide. Specific examples of the aforementioned azo compounds: 2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), 2,2'-azobis(4 -methoxy-2,4-dimethylvaleronitrile), 2,2'-azobis(2-methylbutyronitrile), 4,4'-azobis(4-cyanovaleric acid), 2,2'-Azobis(dimethyl-2-methylpropionate). Specific examples of the aforementioned peroxides: dibenzoyl peroxide, dilauroyl peroxide, tert-butyl peroxypivalate, 1,1-bis(tert butylperoxy)cyclohexane (1,1-di(tert-butylperoxy)cyclohexane), hydrogen peroxide. The above-mentioned polymerization initiators can be used alone or in combination.
本發明之樹脂(A)之重量平均分子量一般為3,000至100,000,較佳為4,000至80,000,更佳為5,000至 60,000。本發明之樹脂(A)之分子量調整,可使用單一樹脂,亦可併用兩種或兩種以上不同分子量之樹脂來達成。 The weight average molecular weight of the resin (A) of the present invention is generally 3,000 to 100,000, preferably 4,000 to 80,000, more preferably 5,000 to 60,000. The molecular weight adjustment of the resin (A) of the present invention can be achieved by using a single resin, or by using two or more resins with different molecular weights in combination.
光酸產生劑(B)Photoacid Generator (B)
光酸產生劑(B)是通過放射線的照射而產生酸的化合物,可使用選自下述結構式(4-1)所表示的肟磺酸酯基的化合物,以及N-磺醯氧基醯亞胺化合物中的至少一種。所述放射線可使用例如可見光線、紫外線、遠紫外線、電子束、X射線等。由於本發明的化學增幅型正型感光性樹脂組成物含有光酸產生劑(B),使得化學增幅型正型感光性樹脂組成物可發揮感放射線(或稱感光)的特性,且可具有良好的放射線感度。做為所述化學增幅型正型感光性樹脂組成物中的光酸產生劑(B),如後所述可以是化合物的形態,也可以是做為構成樹脂(A)的聚合物的一部分而併入樹脂(A)的形態,也可以是此二種形態的結合。此些光酸產生劑(B)可單獨使用,也可以並用2種以上。 The photoacid generator (B) is a compound that generates an acid by irradiation with radiation, and a compound selected from oxime sulfonate groups represented by the following structural formula (4-1), and N-sulfonyloxyacyl at least one of imine compounds. As the radiation, for example, visible rays, ultraviolet rays, deep ultraviolet rays, electron beams, X-rays and the like can be used. Since the chemically amplified positive-type photosensitive resin composition of the present invention contains a photoacid generator (B), the chemically amplified positive-type photosensitive resin composition can exhibit radiation-sensitive (or light-sensitive) characteristics, and can have good radiation sensitivity. The photoacid generator (B) in the chemically amplified positive photosensitive resin composition may be in the form of a compound as described later, or may be formed as a part of the polymer constituting the resin (A). The form incorporated into the resin (A) may also be a combination of these two forms. These photoacid generators (B) may be used individually, and may use 2 or more types together.
光酸產生劑(B)除了含有包含肟磺酸酯基的肟磺酸酯化合物、N-磺醯氧基醯亞胺化合物以外,還可以含有:鎓鹽、含鹵素的化合物、重氮甲烷化合物、碸化合物、磺酸酯化合物、羧酸酯化合物等。 The photoacid generator (B) may contain, in addition to an oxime sulfonate compound containing an oxime sulfonate group, an N-sulfonyloxyimide compound, an onium salt, a halogen-containing compound, a diazomethane compound , Sulfonate compounds, sulfonate compounds, carboxylate compounds, etc.
所述肟磺酸酯化合物為包含如下結構式(4-1)的肟磺酸酯基的化合物。 The oxime sulfonate compound is a compound containing an oxime sulfonate group of the following structural formula (4-1).
於結構式(4-1)中,R20為碳數為1至20的烷基、一價的脂環式烴基、芳基,或是上述基團(烷基、一價的脂環式烴基、芳基)所具有的氫原子被部分或全部取代之基團;以及,*為鍵結處。 In the structural formula (4-1), R20 is an alkyl group with 1 to 20 carbons, a monovalent alicyclic hydrocarbon group, an aryl group, or the above-mentioned groups (alkyl, monovalent alicyclic hydrocarbon group , aryl) is a group in which hydrogen atoms are partially or fully substituted; and, * is a bond.
所述R20所表示的烷基較佳為碳數為1至12的直鏈狀或分支狀的烷基。 The alkyl group represented by R 20 is preferably a linear or branched alkyl group with 1 to 12 carbon atoms.
所述R20所表示的一價脂環式烴基較佳為碳數為4至12的脂環式烴基。 The monovalent alicyclic hydrocarbon group represented by R 20 is preferably an alicyclic hydrocarbon group with 4 to 12 carbon atoms.
所述R20所表示的芳基較佳為碳數為6至20的芳基,更佳為苯基、萘基、甲苯基、二甲苯基。 The aryl group represented by R 20 is preferably an aryl group with 6 to 20 carbon atoms, more preferably phenyl, naphthyl, tolyl, and xylyl.
所述取代基例如可列舉:碳數為1至5的烷基、烷氧基、側氧基、鹵素原子等。 The substituent includes, for example, an alkyl group having 1 to 5 carbon atoms, an alkoxy group, a pendant oxy group, a halogen atom, and the like.
含有結構式(4-1)所表示的肟磺酸酯基的化合物例如可列舉下述式(4-2)至式(4-4)所表示的肟磺酸酯化合物等。 As a compound containing the oxime sulfonate group represented by structural formula (4-1), the oxime sulfonate compound etc. which are represented by following formula (4-2) - a formula (4-4) are mentioned, for example.
所述式(4-2)至式(4-4)中,R21與結構式(4-1)的R20為相同含義。所述式(4-2)及式(4-3)中,R22為碳數為1至12的烷基、碳數為1至12的氟烷基。式(4-4)中,X為烷基、烷氧基、或者鹵素原子。i為0至3的整數。其中,在i為2或3的情況下,多個X可相同,亦可不同。 In the formulas (4-2) to (4-4), R 21 has the same meaning as R 20 in the structural formula (4-1). In the formulas (4-2) and (4-3), R 22 is an alkyl group with 1 to 12 carbons, or a fluoroalkyl group with 1 to 12 carbons. In formula (4-4), X is an alkyl group, an alkoxy group, or a halogen atom. i is an integer of 0 to 3. However, when i is 2 or 3, a plurality of X may be the same or different.
所述X所表示的烷基較佳為碳數為1至4的直鏈狀或分支狀的烷基。所述X所表示的烷氧基較佳為碳數為1至4的直鏈狀或分支狀的烷氧基。所述X所表示的鹵素原子較佳為氯原子、氟原子。 The alkyl group represented by X is preferably a linear or branched alkyl group with 1 to 4 carbon atoms. The alkoxy group represented by X is preferably a linear or branched alkoxy group having 1 to 4 carbon atoms. The halogen atom represented by X is preferably a chlorine atom or a fluorine atom.
所述式(4-4)所表示的肟磺酸酯化合物例如可列舉下述式(4-5)至式(4-9)所表示的化合物等。 Examples of the oxime sulfonate compound represented by the formula (4-4) include compounds represented by the following formula (4-5) to formula (4-9).
所述式(4-5)至式(4-9)所表示的化合物分別為:(5-丙基磺醯氧基亞胺基-5H-噻吩-2-亞基)-(2-甲基苯基)乙腈、(5-辛基磺醯氧基亞胺基-5H-噻吩-2-亞基)-(2-甲基苯基)乙腈、(5-樟腦磺醯氧基亞胺基-5H-噻吩-2-亞基)-(2-甲基苯基)乙腈、(5-對甲苯磺醯氧基亞胺基-5H-噻吩-2-亞基)-(2-甲基苯基)乙腈、2-(辛基磺醯氧基亞胺基)-2-(4-甲氧基苯基)乙腈、4-甲基苯基磺醯氧基亞胺基-α-(4-甲氧基苯基)乙腈,可使用市售的上述化合物。 The compounds represented by the formula (4-5) to the formula (4-9) are respectively: (5-propylsulfonyloxyimino-5H-thiophene-2-ylidene)-(2-methyl Phenyl)acetonitrile, (5-octylsulfonyloxyimino-5H-thiophene-2-ylidene)-(2-methylphenyl)acetonitrile, (5-camphorsulfonyloxyimino- 5H-thiophene-2-ylidene)-(2-methylphenyl)acetonitrile, (5-p-toluenesulfonyloxyimino-5H-thiophene-2-ylidene)-(2-methylphenyl ) acetonitrile, 2-(octylsulfonyloxyimino)-2-(4-methoxyphenyl)acetonitrile, 4-methylphenylsulfonyloxyimino-α-(4-methyl (oxyphenyl)acetonitrile, commercially available above-mentioned compounds can be used.
上述N-磺醯氧基醯亞胺化合物例如可列舉:N-(三氟甲基磺醯氧基)丁二醯亞胺、N-(樟腦磺醯氧基)丁 二醯亞胺、N-(4-甲基苯基磺醯氧基)丁二醯亞胺、N-(2-三氟甲基苯基磺醯氧基)丁二醯亞胺、N-(4-氟苯基磺醯氧基)丁二醯亞胺、N-(三氟甲基磺醯氧基)鄰苯二甲醯亞胺、N-(樟腦磺醯氧基)鄰苯二甲醯亞胺、N-(2-三氟甲基苯基磺醯氧基)鄰苯二甲醯亞胺、N-(2-氟苯基磺醯氧基)鄰苯二甲醯亞胺、N-(三氟甲基磺醯氧基)二苯基順丁烯二醯亞胺、N-(樟腦磺醯氧基)二苯基順丁烯二醯亞胺、(4-甲基苯基磺醯氧基)二苯基順丁烯二醯亞胺、N-(2-三氟甲基苯基磺醯氧基)二苯基順丁烯二醯亞胺、N-(4-氟苯基磺醯氧基)二苯基順丁烯二醯亞胺、N-(苯基磺醯氧基)雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(4-甲基苯基磺醯氧基)雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(三氟甲磺醯氧基)雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(九氟丁磺醯氧基)雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(樟腦磺醯氧基)雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(樟腦磺醯氧基)-7-氧雜雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(三氟甲基磺醯氧基)-7-氧雜雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(4-甲基苯基磺醯氧基)雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(4-甲基苯基磺醯氧基)-7-氧雜雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(2-三氟甲基苯基磺醯氧基)雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(2-三氟甲基苯基磺醯氧基)-7-氧雜雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(4-氟苯基磺醯氧基)雙環[2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(4-氟苯基磺醯氧基)-7-氧雜雙環 [2.2.1]庚-5-烯-2,3-二羧基醯亞胺、N-(三氟甲基磺醯氧基)雙環[2.2.1]庚烷-5,6-氧基-2,3-二羧基醯亞胺、N-(樟腦磺醯氧基)雙環[2.2.1]庚烷-5,6-氧基-2,3-二羧基醯亞胺、N-(4-甲基苯基磺醯氧基)雙環[2.2.1]庚烷-5,6-氧基-2,3-二羧基醯亞胺、N-(2-三氟甲基苯基磺醯氧基)雙環[2.2.1]庚烷-5,6-氧基-2,3-二羧基醯亞胺、N-(4-氟苯基磺醯氧基)雙環[2.2.1]庚烷-5,6-氧基-2,3-二羧基醯亞胺、N-(三氟甲基磺醯氧基)萘二甲醯亞胺(N-((trifluoromethylsulfonyl)oxy)naphthalene dicarboximide)、N-(樟腦磺醯氧基)萘二甲醯亞胺、N-(4-甲基苯基磺醯氧基)萘二甲醯亞胺、N-(苯基磺醯氧基)萘二甲醯亞胺、N-(2-三氟甲基苯基磺醯氧基)萘二甲醯亞胺、N-(4-氟苯基磺醯氧基)萘二甲醯亞胺、N-(五氟乙基磺醯氧基)萘二甲醯亞胺、N-(七氟丙基磺醯氧基)萘二甲醯亞胺、N-(九氟丁基磺醯氧基)萘二甲醯亞胺、N-(乙基磺醯氧基)萘二甲醯亞胺、N-(丙基磺醯氧基)萘二甲醯亞胺、N-(丁基磺醯氧基)萘二甲醯亞胺、N-(戊基磺醯氧基)萘二甲醯亞胺、N-(己基磺醯氧基)萘二甲醯亞胺、N-(庚基磺醯氧基)萘二甲醯亞胺、N-(辛基磺醯氧基)萘二甲醯亞胺、N-(壬基磺醯氧基)萘二甲醯亞胺等。 The aforementioned N-sulfonyloxyimide compounds include, for example, N-(trifluoromethylsulfonyloxy)succinimide, N-(camphorsulfonyloxy)butyl Diimide, N-(4-methylphenylsulfonyloxy)succinimide, N-(2-trifluoromethylphenylsulfonyloxy)succinimide, N-( 4-Fluorophenylsulfonyloxy)succinimide, N-(trifluoromethylsulfonyloxy)phthalimide, N-(camphorsulfonyloxy)phthalimide imine, N-(2-trifluoromethylphenylsulfonyloxy)phthalimide, N-(2-fluorophenylsulfonyloxy)phthalimide, N- (Trifluoromethylsulfonyloxy)diphenylmaleimide, N-(camphorsulfonyloxy)diphenylmaleimide, (4-methylphenylsulfonyl Oxy)diphenylmaleimide, N-(2-trifluoromethylphenylsulfonyloxy)diphenylmaleimide, N-(4-fluorophenylsulfonyl Acyloxy)diphenylmaleimide, N-(phenylsulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-( 4-methylphenylsulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(trifluoromethanesulfonyloxy)bicyclo[2.2.1] Hept-5-ene-2,3-dicarboxyimide, N-(nonafluorobutanesulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N -(camphorsulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(camphorsulfonyloxy)-7-oxabicyclo[2.2.1] Hept-5-ene-2,3-dicarboxyimide, N-(trifluoromethylsulfonyloxy)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-di Carboxylimide, N-(4-methylphenylsulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(4-methylphenyl Sulfonyloxy)-7-oxabicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N-(2-trifluoromethylphenylsulfonyloxy)bicyclo[ 2.2.1] Hept-5-ene-2,3-dicarboxyimide, N-(2-trifluoromethylphenylsulfonyloxy)-7-oxabicyclo[2.2.1]hept-5 -ene-2,3-dicarboxyimide, N-(4-fluorophenylsulfonyloxy)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxyimide, N- (4-Fluorophenylsulfonyloxy)-7-oxabicyclo [2.2.1] Hept-5-ene-2,3-dicarboxyimide, N-(trifluoromethylsulfonyloxy)bicyclo[2.2.1]heptane-5,6-oxyl-2 ,3-Dicarboxyimide, N-(camphorsulfonyloxy)bicyclo[2.2.1]heptane-5,6-oxyl-2,3-dicarboxyimide, N-(4-methyl phenylsulfonyloxy)bicyclo[2.2.1]heptane-5,6-oxy-2,3-dicarboxyimide, N-(2-trifluoromethylphenylsulfonyloxy) Bicyclo[2.2.1]heptane-5,6-oxyl-2,3-dicarboxyimide, N-(4-fluorophenylsulfonyloxy)bicyclo[2.2.1]heptane-5, 6-Oxy-2,3-dicarboxyimide, N-(trifluoromethylsulfonyloxy)naphthalene dicarboximide (N-((trifluoromethylsulfonyl)oxy)naphthalene dicarboximide), N-(camphor Sulfonyloxy)naphthalimide, N-(4-methylphenylsulfonyloxy)naphthalimide, N-(phenylsulfonyloxy)naphthalimide, N-(2-trifluoromethylphenylsulfonyloxy)naphthalimide, N-(4-fluorophenylsulfonyloxy)naphthalimide, N-(pentafluoroethyl Sulfonyloxy)naphthalimide, N-(heptafluoropropylsulfonyloxy)naphthalimide, N-(nonafluorobutylsulfonyloxy)naphthalimide, N-(ethylsulfonyloxy)naphthalimide, N-(propylsulfonyloxy)naphthalimide, N-(butylsulfonyloxy)naphthalimide , N-(pentylsulfonyloxy)naphthalimide, N-(hexylsulfonyloxy)naphthalimide, N-(heptylsulfonyloxy)naphthalimide , N-(octylsulfonyloxy)naphthalimide, N-(nonylsulfonyloxy)naphthalimide, etc.
所述鎓鹽、含鹵素的化合物、重氮甲烷化合物、碸化合物、磺酸酯化合物、羧酸酯化合物等可使用日本專利特開2011-232632號公報中記載的化合物。例如:苄基(4-羥苯基)甲基硫鎓六氟銻酸鹽。 As the onium salt, halogen-containing compound, diazomethane compound, sulfonate compound, sulfonate compound, carboxylate compound, etc., compounds described in JP-A-2011-232632 can be used. For example: benzyl(4-hydroxyphenyl)methylsulfonium hexafluoroantimonate.
基於所述樹脂(A)的使用量為100重量份,所述光酸產生劑(B)的使用量為0.1重量份至10重量份,較佳為0.1重量份至8重量份,更佳為0.5重量份至6重量份。若化學增幅型正型感光性樹脂組成物中含有結構式(4-1)之肟磺酸酯基的化合物做為所述光酸產生劑(B),所製得的保護膜具有耐化性佳的優點。 Based on 100 parts by weight of the resin (A), the photoacid generator (B) is used in an amount of 0.1 to 10 parts by weight, preferably 0.1 to 8 parts by weight, more preferably 0.5 parts by weight to 6 parts by weight. If the compound containing the oxime sulfonate group of structural formula (4-1) is used as the photoacid generator (B) in the chemically amplified positive photosensitive resin composition, the prepared protective film has chemical resistance Good advantage.
溶劑(C)solvent (C)
本發明之溶劑(C)的種類沒有特別的限制。溶劑(C)之具體例為含醇式羥基(alcoholic hydroxy)的化合物或含羰基(carbonyl group)的環狀化合物等。 The type of solvent (C) in the present invention is not particularly limited. Specific examples of the solvent (C) include alcoholic hydroxyl-containing compounds, carbonyl group-containing cyclic compounds, and the like.
含醇式羥基的化合物之具體例為丙酮醇(acetol)、3-羥基-3-甲基-2-丁酮(3-hydroxy-3-methyl-2-butanone)、4-羥基-3-甲基-2-丁酮(4-hydroxy-3-methyl-2-butanone)、5-羥基-2-戊酮(5-hydroxy-2-pentanone)、4-羥基-4-甲基-2-戊酮(4-hydroxy-4-methyl-2-pentanone)(亦稱為二丙酮醇(diacetone alcohol,簡稱DAA))、乳酸乙酯(ethyl lactate)、乳酸丁酯(butyl lactate)、丙二醇單甲醚propylene glycol monomethyl ether)、丙二醇單乙醚(propylene glycol monoethyl ether,簡稱PGEE)、丙二醇甲醚醋酸酯(propylene glycol monomethyl ether acetate,簡稱PGMEA)、丙二醇單正丙醚(propylene glycol mono-n-propyl ether)、丙二醇單正丁醚(propylene glycol mono-n-butyl ether)、丙二醇單第三 丁醚(propylene glycol mono-t-butyl ether)、二乙二醇甲乙醚(diethylene glycol methyl ethyl ether)、3-甲氧基-1-丁醇(3-methoxy-1-butanol)、3-甲基-3-甲氧基-1-丁醇(3-methyl-3-methoxy-1-butanol)或其組合。值得注意的是,含醇式羥基的化合物較佳為二丙酮醇、乳酸乙酯、丙二醇單乙醚、丙二醇甲醚醋酸酯或其組合。含醇式羥基的化合物可單獨使用或組合多種來使用。 Specific examples of compounds containing alcoholic hydroxyl groups are acetol (acetol), 3-hydroxy-3-methyl-2-butanone (3-hydroxy-3-methyl-2-butanone), 4-hydroxy-3-methyl Base-2-butanone (4-hydroxy-3-methyl-2-butanone), 5-hydroxy-2-pentanone (5-hydroxy-2-pentanone), 4-hydroxy-4-methyl-2-pentanone Ketone (4-hydroxy-4-methyl-2-pentanone) (also known as diacetone alcohol (DAA)), ethyl lactate (ethyl lactate), butyl lactate (butyl lactate), propylene glycol monomethyl ether Propylene glycol monomethyl ether), propylene glycol monoethyl ether (PGEE for short), propylene glycol monomethyl ether acetate (PGMEA for short), propylene glycol mono-n-propyl ether , Propylene glycol mono-n-butyl ether, Propylene glycol mono-n-butyl ether Butyl ether (propylene glycol mono-t-butyl ether), diethylene glycol methyl ethyl ether (diethylene glycol methyl ethyl ether), 3-methoxy-1-butanol (3-methoxy-1-butanol), 3-methyl Base-3-methoxy-1-butanol (3-methyl-3-methoxy-1-butanol) or a combination thereof. It should be noted that the compound containing alcoholic hydroxyl group is preferably diacetone alcohol, ethyl lactate, propylene glycol monoethyl ether, propylene glycol methyl ether acetate or a combination thereof. The alcoholic hydroxyl group-containing compound can be used alone or in combination.
含羰基的環狀化合物之具體例為γ-丁內酯(γ-butyrolactone)、γ-戊內酯(γ-valerolactone)、δ-戊內酯(δ-valerolactone)、碳酸丙烯酯(propylene carbonate)、氮-甲基吡咯烷酮(N-methyl pyrrolidone)、環己酮(cyclohexanone)或環庚酮(cycloheptanone)等。值得注意的是,含羰基的環狀化合物較佳為γ-丁內酯、氮-甲基吡咯烷酮、環己酮或其組合。含羰基的環狀化合物可單獨使用或組合多種來使用。 Specific examples of carbonyl-containing cyclic compounds are γ-butyrolactone (γ-butyrolactone), γ-valerolactone (γ-valerolactone), δ-valerolactone (δ-valerolactone), propylene carbonate (propylene carbonate) , N-methyl pyrrolidone (N-methyl pyrrolidone), cyclohexanone (cyclohexanone) or cycloheptanone (cycloheptanone), etc. It should be noted that the carbonyl-containing cyclic compound is preferably γ-butyrolactone, nitrogen-methylpyrrolidone, cyclohexanone or a combination thereof. The carbonyl group-containing cyclic compound can be used alone or in combination.
含醇式羥基的化合物可與含羰基的環狀化合物組合使用,且其重量比率沒有特別限制。含醇式羥基的化合物與含羰基的環狀化合物的重量比值較佳為99/1至50/50;更佳為95/5至60/40。 The alcoholic hydroxyl group-containing compound may be used in combination with the carbonyl group-containing cyclic compound, and the weight ratio thereof is not particularly limited. The weight ratio of the alcoholic hydroxyl-containing compound to the carbonyl-containing cyclic compound is preferably 99/1 to 50/50; more preferably 95/5 to 60/40.
在不損及本發明的效果的範圍內,亦可以含有其他溶劑。該其他溶劑之具體例為:(1)酯類:醋酸乙酯、醋酸正丙酯、醋酸異丙酯、醋酸正丁酯、醋酸異丁酯、丙二醇甲醚醋酸酯、3-甲氧基-1-醋酸丁酯或3-甲基-3-甲氧基-1-醋酸丁酯等;(2)酮類:甲基異丁酮、二異丙酮或二異丁 酮等;或者(3)醚類:二乙醚、二異丙醚、二正丁醚或二苯醚等。 Other solvents may also be contained within the range not impairing the effect of the present invention. Specific examples of the other solvents are: (1) Esters: ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, propylene glycol methyl ether acetate, 3-methoxy- 1-butyl acetate or 3-methyl-3-methoxy-1-butyl acetate, etc.; (2) Ketones: methyl isobutyl ketone, diisopropanone or diisobutyl Ketones, etc.; or (3) ethers: diethyl ether, diisopropyl ether, di-n-butyl ether or diphenyl ether, etc.
基於所述樹脂(A)的使用量為100重量份所述溶劑(C)的使用量為200重量份至2000重量份,較佳為300重量份至1800重量份,更佳為500重量份至1500重量份。 Based on 100 parts by weight of the resin (A), the solvent (C) is used in an amount of 200 parts by weight to 2000 parts by weight, preferably 300 parts by weight to 1800 parts by weight, more preferably 500 parts by weight to 1500 parts by weight.
其他添加劑(D)Other additives (D)
選擇性地,本發明的化學增幅型正型感光性樹脂組成物可包含其他添加劑(D)。具體而言,其他添加劑(D)之具體例為增感劑(sensitizer)、密著助劑(adhesion auxiliary agent)、界面活性劑(surfactant)、溶解促進劑(solubility promoter)、消泡劑(defoamer)或其組合。 Optionally, the chemically amplified positive photosensitive resin composition of the present invention may contain other additives (D). Specifically, specific examples of other additives (D) include sensitizers, adhesion auxiliary agents, surfactants, solubility promoters, and defoamers. ) or a combination thereof.
增感劑的種類並無特別的限制。增感劑較佳為使用含有酚式羥基(phenolic hydroxy)的化合物,之具體例為:(1)三苯酚型化合物(trisphenol type compound):如三(4-羥基苯基)甲烷、雙(4-羥基-3-甲基苯基)-2-羥基苯基甲烷、雙(4-羥基-2,3,5-三甲基苯基)-2-羥基苯基甲烷、雙(4-羥基-3,5-二甲基苯基)-4-羥基苯基甲烷、雙(4-羥基-3,5-二甲基苯基)-3-羥基苯基甲烷、雙(4-羥基-3,5-甲基苯基)-2-羥基苯基甲烷、雙(4-羥基-2,5-二甲基苯基)-4-羥基苯基甲烷、雙(4-羥基-2,5-二甲基苯基)-3-羥基苯基甲烷、雙(4-羥基-2,5-二甲基苯基)-2-羥基苯基甲烷、雙(4-羥基-3,5-二甲基苯基)-3,4-二羥基苯基甲烷、雙(4-羥基-2,5-二甲基苯基)-3,4-二羥基苯基甲烷、雙(4-羥基-2,5- 二甲基苯基)-2,4-二羥基苯基甲烷、雙(4-羥基苯基)-3-甲氧基-4-羥基苯基甲烷、雙(5-環己基-4-羥基-2-甲基苯基)-4-羥基苯基甲烷、雙(5-環己基-4-羥基-2-甲基苯基)-3-羥基苯基甲烷、雙(5-環己基-4-羥基-2-甲基苯基)-2-羥基苯基甲烷或雙(5-環己基-4-羥基-2-甲基苯基)-3,4-二羥基苯基甲烷等;(2)雙苯酚型化合物(bisphenol type compound):如雙(2,3,4-三羥基苯基)甲烷、雙(2,4-二羥基苯基)甲烷、2,3,4-三羥基苯基-4'-羥基苯基甲烷、2-(2,3,4-三羥基苯基)-2-(2',3',4'-三羥基苯基)丙烷、2-(2,4-二羥基苯基)-2-(2',4'-二羥基苯基)丙烷、2-(4-羥基苯基)-2-(4'-羥基苯基)丙烷、2-(3-氟基-4-羥基苯基)-2-(3'-氟基-4'-羥基苯基)丙烷、2-(2,4-二羥基苯基)-2-(4'-羥基苯基)丙烷、2-(2,3,4-三羥基苯基)-2-(4'-羥基苯基)丙烷或2-(2,3,4-三羥基苯基)-2-(4'-羥基-3',5'-二甲基苯基)丙烷等;(3)多核分枝型化合物(polynuclear branched compound):如1-[1-(4-羥基苯基)異丙基]-4-[1,1-雙(4-羥基苯基)乙基]苯或1-[1-(3-甲基-4-羥基苯基)異丙基]-4-[1,1-雙(3-甲基-4-羥基苯基)乙基]苯等;(4)縮合型苯酚化合物(condensation type phenol compound):如1,1-雙(4-羥基苯基)環己烷等;(5)多羥基二苯甲酮類(polyhydroxy benzophenone):如2,3,4-三羥基二苯甲酮、2,4,4'-三羥基二苯甲酮、2,4,6-三羥基二苯甲酮、2,3,4-三羥基-2'-甲 基二苯甲酮、2,3,4,4'-四羥基二苯甲酮、2,4,2',4'-四羥基二苯甲酮、2,4,6,3',4'-五羥基二苯甲酮、2,3,4,2',4'-五羥基二苯甲酮、2,3,4,2',5'-五羥基二苯甲酮、2,4,6,3',4',5'-六羥基二苯甲酮或2,3,4,3',4',5'-六羥基二苯甲酮等;或(6)上述各種類含有酚式羥基的化合物的組合。 The kind of sensitizer is not particularly limited. The sensitizer is preferably a compound containing a phenolic hydroxyl. Specific examples are: (1) trisphenol type compound: such as tris(4-hydroxyphenyl)methane, bis(4 -Hydroxy-3-methylphenyl)-2-hydroxyphenylmethane, bis(4-hydroxy-2,3,5-trimethylphenyl)-2-hydroxyphenylmethane, bis(4-hydroxy- 3,5-Dimethylphenyl)-4-hydroxyphenylmethane, bis(4-hydroxy-3,5-dimethylphenyl)-3-hydroxyphenylmethane, bis(4-hydroxy-3, 5-methylphenyl)-2-hydroxyphenylmethane, bis(4-hydroxy-2,5-dimethylphenyl)-4-hydroxyphenylmethane, bis(4-hydroxy-2,5-di Methylphenyl)-3-hydroxyphenylmethane, bis(4-hydroxy-2,5-dimethylphenyl)-2-hydroxyphenylmethane, bis(4-hydroxy-3,5-dimethyl Phenyl)-3,4-dihydroxyphenylmethane, bis(4-hydroxy-2,5-dimethylphenyl)-3,4-dihydroxyphenylmethane, bis(4-hydroxy-2,5 - Dimethylphenyl)-2,4-dihydroxyphenylmethane, bis(4-hydroxyphenyl)-3-methoxy-4-hydroxyphenylmethane, bis(5-cyclohexyl-4-hydroxy- 2-methylphenyl)-4-hydroxyphenylmethane, bis(5-cyclohexyl-4-hydroxy-2-methylphenyl)-3-hydroxyphenylmethane, bis(5-cyclohexyl-4- Hydroxy-2-methylphenyl)-2-hydroxyphenylmethane or bis(5-cyclohexyl-4-hydroxy-2-methylphenyl)-3,4-dihydroxyphenylmethane, etc.; (2) Bisphenol type compound: such as bis(2,3,4-trihydroxyphenyl)methane, bis(2,4-dihydroxyphenyl)methane, 2,3,4-trihydroxyphenyl- 4'-Hydroxyphenylmethane, 2-(2,3,4-trihydroxyphenyl)-2-(2',3',4'-trihydroxyphenyl)propane, 2-(2,4-bis Hydroxyphenyl)-2-(2',4'-dihydroxyphenyl)propane, 2-(4-hydroxyphenyl)-2-(4'-hydroxyphenyl)propane, 2-(3-fluoro -4-hydroxyphenyl)-2-(3'-fluoro-4'-hydroxyphenyl)propane, 2-(2,4-dihydroxyphenyl)-2-(4'-hydroxyphenyl)propane , 2-(2,3,4-trihydroxyphenyl)-2-(4'-hydroxyphenyl)propane or 2-(2,3,4-trihydroxyphenyl)-2-(4'-hydroxyl -3',5'-dimethylphenyl) propane, etc.; (3) polynuclear branched compound: such as 1-[1-(4-hydroxyphenyl)isopropyl]-4- [1,1-bis(4-hydroxyphenyl)ethyl]benzene or 1-[1-(3-methyl-4-hydroxyphenyl)isopropyl]-4-[1,1-bis(3 -methyl-4-hydroxyphenyl)ethyl]benzene, etc.; (4) condensation type phenol compound: such as 1,1-bis(4-hydroxyphenyl)cyclohexane, etc.; (5 ) polyhydroxy benzophenone (polyhydroxy benzophenone): such as 2,3,4-trihydroxy benzophenone, 2,4,4'-trihydroxy benzophenone, 2,4,6-trihydroxy dibenzophenone Benzophenone, 2,3,4-trihydroxy-2'-methanol 2,3,4,4'-tetrahydroxybenzophenone, 2,4,2',4'-tetrahydroxybenzophenone, 2,4,6,3',4' -pentahydroxybenzophenone, 2,3,4,2',4'-pentahydroxybenzophenone, 2,3,4,2',5'-pentahydroxybenzophenone, 2,4, 6,3',4',5'-hexahydroxybenzophenone or 2,3,4,3',4',5'-hexahydroxybenzophenone, etc.; or (6) the above-mentioned types contain phenol Combinations of compounds of the formula hydroxy.
基於樹脂(A)之使用量為100重量份,增感劑之使用量為5重量份至50重量份;較佳為8重量份至40重量份;且更佳為10重量份至35重量份。 Based on the usage amount of resin (A) being 100 parts by weight, the usage amount of sensitizer is 5 parts by weight to 50 parts by weight; preferably 8 parts by weight to 40 parts by weight; and more preferably 10 parts by weight to 35 parts by weight .
密著助劑之具體例為三聚氰胺(melamine)化合物及矽烷系化合物等。密著助劑的作用在於增加由光硬化性聚矽氧烷組成物所形成的薄膜與元件或基板之間的密著性。 Specific examples of the adhesion aid include melamine compounds, silane compounds, and the like. The role of the adhesion aid is to increase the adhesion between the film formed by the photocurable polysiloxane composition and the device or the substrate.
三聚氰胺的市售品之具體例為由三井化學製造的商品名為Cymel-300或Cymel-303等;或者由三和化學製造的商品名為MW-30MH、MW-30、MS-11、MS-001、MX-750或MX-706等。 Specific examples of commercially available products of melamine are Cymel-300 or Cymel-303 manufactured by Mitsui Chemicals; or MW-30MH, MW-30, MS-11, MS- 001, MX-750 or MX-706 etc.
當使用三聚氰胺化合物做為密著助劑時,基於該樹脂(A)之使用量為100重量份,三聚氰胺化合物之使用量為0重量份至20重量份;較佳為0.5重量份至18重量份;且更佳為1.0重量份至15重量份。 When using a melamine compound as an adhesion aid, based on 100 parts by weight of the resin (A), the amount of the melamine compound used is 0 to 20 parts by weight; preferably 0.5 to 18 parts by weight ; And more preferably from 1.0 parts by weight to 15 parts by weight.
矽烷系化合物之具體例為乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、3-丙烯醯氧基丙基三甲氧基矽烷、乙烯基三(2-甲氧基乙氧基)矽烷、氮-(2-胺基乙基)-3-胺基丙基甲基二甲氧基矽烷、氮-(2-胺基乙基)-3-胺基丙基 三甲氧基矽烷、3-胺丙基三乙氧基矽烷、3-環氧丙氧基丙基三甲氧基矽烷、3-環氧丙氧基丙基二甲基甲氧基矽烷、2-(3,4-環氧環己基)乙基三甲氧基矽烷、3-氯丙基甲基二甲氧基矽烷、3-氯丙基三甲氧基矽烷、3-甲基丙烯醯氧基丙基三甲氧基矽烷、3-巰丙基三甲氧基矽烷或由信越化學公司製造的市售品(商品名如KBM403)等。 Specific examples of silane compounds are vinyltrimethoxysilane, vinyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, vinyltris(2-methoxyethoxy)silane, Nitrogen-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, Nitrogen-(2-aminoethyl)-3-aminopropyl Trimethoxysilane, 3-Aminopropyltriethoxysilane, 3-Glycidoxypropyltrimethoxysilane, 3-Glycidoxypropyldimethylmethoxysilane, 2-( 3,4-Epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane Oxysilane, 3-mercaptopropyltrimethoxysilane, or a commercial product manufactured by Shin-Etsu Chemical Co., Ltd. (trade name such as KBM403) and the like.
當使用矽烷系化合物作為密著助劑時,基於樹脂(A)之使用量為100重量份,矽烷系化合物之使用量為0重量份至2重量份;較佳為0.05重量份至1重量份;且更佳為0.1重量份至0.8重量份。 When using a silane compound as an adhesion aid, based on 100 parts by weight of the resin (A), the amount of the silane compound used is 0 to 2 parts by weight; preferably 0.05 to 1 part by weight ; And more preferably 0.1 to 0.8 parts by weight.
界面活性劑之具體例為陰離子系界面活性劑、陽離子系界面活性劑、非離子系界面活性劑、兩性界面活性劑、聚矽氧烷系界面活性劑、氟系界面活性劑或其組合。 Specific examples of surfactants are anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, polysiloxane-based surfactants, fluorine-based surfactants, or combinations thereof.
界面活性劑的實例包括(1)聚乙二醇烷基醚類(polyoxyethylene alkyl ethers):聚乙二醇十二烷基醚等;(2)聚乙二醇烷基苯基醚類(polyoxyethylene phenyl ethers):聚乙二醇辛基苯基醚、聚乙二醇壬基苯基醚等;(3)聚乙二醇二酯類(polyethylene glycol diesters):聚乙二醇二月桂酸酯、聚乙二醇二硬酸酯等;(4)山梨糖醇酐脂肪酸酯類(sorbitan fatty acid esters);以及(5)經脂肪酸改質的聚酯類(fatty acid modified poly esters);及(6)經三級胺改質的聚胺基甲酸酯類(tertiary amine modified polyurethanes)等。界面活性劑的市售商品之具體例為KP(由信越化學工業製造)、SF-8427(由道康寧東麗聚矽氧 股份有限公司(Dow Corning Toray Silicone Co.,Ltd.)製造)、Polyflow(由共榮社油脂化學工業製造)、F-Top(由得克姆股份有限公司製造(Tochem Products Co.,Ltd.)製造)、Megaface(由大日本印墨化學工業(DIC)製造)、Fluorade(由住友3M股份有限公司(Sumitomo 3M Ltd.)製造)、Surflon(由旭硝子製造)、SINOPOL E8008(由中日合成化學製造)、F-475(由大日本印墨化學工業製造)或其組合。 Examples of surfactants include (1) polyethylene glycol alkyl ethers (polyoxyethylene alkyl ethers): polyethylene glycol lauryl ether, etc.; (2) polyethylene glycol alkyl phenyl ethers (polyoxyethylene phenyl ethers): polyethylene glycol octylphenyl ether, polyethylene glycol nonylphenyl ether, etc.; (3) polyethylene glycol diesters: polyethylene glycol dilaurate, polyethylene glycol diesters Ethylene glycol distearate, etc.; (4) sorbitan fatty acid esters; and (5) fatty acid modified polyesters; and (6) Polyurethanes modified by tertiary amines (tertiary amine modified polyurethanes), etc. Specific examples of commercially available surfactants are KP (manufactured by Shin-Etsu Chemical Industry), SF-8427 (manufactured by Dow Corning Toray Polysiloxane Co., Ltd. Co., Ltd. (manufactured by Dow Corning Toray Silicone Co., Ltd.), Polyflow (manufactured by Kyoeisha Oleochemical Industry), F-Top (manufactured by Tochem Products Co., Ltd.) Manufactured), Megaface (manufactured by Dainippon Ink Chemical Industry (DIC)), Fluorade (manufactured by Sumitomo 3M Ltd.), Surflon (manufactured by Asahi Glass), SINOPOL E8008 (manufactured by Sino-Nippon Synthetic Chemicals Manufactured), F-475 (manufactured by Dainippon Ink Chemical Industry Co., Ltd.), or a combination thereof.
基於樹脂(A)之使用量為100重量份,界面活性劑之使用量為0.5重量份至50重量份;較佳為1重量份至40重量份;且更佳為3至30重量份。 Based on 100 parts by weight of the resin (A), the used amount of the surfactant is 0.5 to 50 parts by weight; preferably 1 to 40 parts by weight; and more preferably 3 to 30 parts by weight.
消泡劑的實例包括Surfynol MD-20、Surfynol MD-30、EnviroGem AD01、EnviroGem AE01、EnviroGem AE02、Surfynol DF110D、Surfynol 104E、Surfynol 420、Surfynol DF37、Surfynol DF58、Surfynol DF66、Surfynol DF70以及Surfynol DF210(由氣體產品(Air products)製造)等。 Examples of antifoaming agents include Surfynol MD-20, Surfynol MD-30, EnviroGem AD01, EnviroGem AE01, EnviroGem AE02, Surfynol DF110D, Surfynol 104E, Surfynol 420, Surfynol DF37, Surfynol DF58, Surfynol DF66, Surfynol Gas products (Air products) manufacturing), etc.
基於樹脂(A)之使用量為100重量份,消泡劑之使用量為1重量份至10重量份;較佳為2重量份至9重量份;且更佳為3重量份至8重量份。 Based on the amount of resin (A) used as 100 parts by weight, the amount of antifoaming agent used is 1 to 10 parts by weight; preferably 2 to 9 parts by weight; and more preferably 3 to 8 parts by weight .
溶解促進劑的實例包括氮-羥基二羧基醯亞胺化合物(N-hydroxydicarboxylic imide)以及含酚式羥基的化合物。溶解促進劑之具體例為鄰萘醌二疊氮磺酸酯(B)中所使用的含酚式羥基的化合物。 Examples of the dissolution accelerator include N-hydroxydicarboxylic imide compounds (N-hydroxydicarboxylic imide) and compounds containing phenolic hydroxyl groups. A specific example of the dissolution accelerator is a phenolic hydroxyl group-containing compound used for o-naphthoquinonediazidesulfonate (B).
基於樹脂(A)之使用量為100重量份,溶解促進劑之使用量為1重量份至20重量份;較佳為2重量份至15重量份;且更佳為3重量份至10重量份。 Based on 100 parts by weight of the resin (A), the usage of the dissolution accelerator is 1 to 20 parts by weight; preferably 2 to 15 parts by weight; and more preferably 3 to 10 parts by weight .
化學增幅型正型感光性樹脂組成物之具體例為以下列方式來製備:將樹脂(A)、光酸產生劑(B)以及溶劑(C)放置於攪拌器中攪拌,使其均勻混合成溶液狀態,必要時,可添加其他添加劑(D)。 A specific example of the chemically amplified positive-type photosensitive resin composition is prepared in the following manner: the resin (A), the photoacid generator (B) and the solvent (C) are placed in a stirrer and stirred to make them uniformly mixed into a In solution state, other additives (D) may be added if necessary.
本發明亦提供一種保護膜,其包含將上述化學增幅型正型感光性樹脂組成物塗佈於基材上,再經預烤、曝光、顯影及後烤處理後所形成。 The present invention also provides a protective film, which is formed by coating the above-mentioned chemically amplified positive-type photosensitive resin composition on a substrate, followed by pre-baking, exposure, development and post-baking.
本發明更提供一種具有保護膜的元件,其包含基材以及所述保護膜。 The present invention further provides an element with a protective film, which includes a substrate and the protective film.
保護膜的形成方法Formation method of protective film
在一些實施例中,本發明的化學增幅型正型感光性樹脂組成物可用於顯示元件的保護膜之形成材料。另外,本發明也包含適用於由化學增幅型正型感光性樹脂組成物形成的顯示元件用保護膜。 In some embodiments, the chemically amplified positive photosensitive resin composition of the present invention can be used as a material for forming a protective film of a display device. Moreover, this invention also includes the protective film for display elements which are applicable to the chemical amplification type positive photosensitive resin composition.
所述保護膜的形成方法包括下述步驟:(1)使用化學增幅型正型感光性樹脂組成物,在基板上形成塗膜的步驟(以下也稱為“步驟(1)”);(2)對上述塗膜的至少一部分照射放射線的步驟(以下也稱為“步驟(2)”);(3)對照射放射線後的上述塗膜進行顯影的步驟(以下也稱為“步驟(3)”);以及 (4)對顯影後的上述塗膜進行加熱的步驟(以下也稱為“步驟(4)”)。 The forming method of the protective film comprises the following steps: (1) using a chemically amplified positive-type photosensitive resin composition to form a coating film on a substrate (hereinafter also referred to as "step (1)"); (2 ) a step of irradiating at least a part of the coating film with radiation (hereinafter also referred to as "step (2)"); (3) a step of developing the coating film after irradiation with radiation (hereinafter also referred to as "step (3) ");as well as (4) The process (henceforth "process (4)") of heating the said coating film after image development.
依據此形成方法,能夠形成表面硬度、耐溶劑性、耐熱性以及電壓保持率優異的顯示元件用保護膜。另外,藉由使用具有良好感度的化學增幅型正型感光性樹脂組成物,能夠容易地形成具有微細且精巧的圖案的顯示元件用保護膜。因此,所形成的顯示元件用保護膜適用於液晶顯示元件、有機EL顯示元件等顯示元件。 According to this formation method, a protective film for a display element excellent in surface hardness, solvent resistance, heat resistance, and voltage retention can be formed. Moreover, the protective film for display elements which have a fine and fine pattern can be formed easily by using the chemically amplified positive type photosensitive resin composition which has favorable sensitivity. Therefore, the formed protective film for display elements is suitable for display elements such as liquid crystal display elements and organic EL display elements.
[步驟(1)] [step 1)]
本步驟中,將化學增幅型正型感光性樹脂組成物塗佈於基板上而形成塗膜。較佳地,藉由預烘烤塗佈面而去除溶劑。 In this step, the chemically amplified positive photosensitive resin composition is coated on the substrate to form a coating film. Preferably, the solvent is removed by pre-baking the coated side.
基板例如可列舉:玻璃、石英、矽基材、樹脂等。樹脂例如可列舉:聚對苯二甲酸乙二酯、聚對苯二甲酸丁二酯、聚醚碸、聚碳酸酯、聚醯亞胺、環狀烯烴的開環聚合物以及其氫化物等。預烘烤的條件也根據各成分的種類、調配比例等而有所不同,可設為70℃至120℃、1分鐘至10分鐘左右。 Examples of the substrate include glass, quartz, silicon substrates, resins, and the like. Examples of the resin include polyethylene terephthalate, polybutylene terephthalate, polyethersulfone, polycarbonate, polyimide, ring-opened polymers of cyclic olefins, hydrogenated products thereof, and the like. The prebaking conditions also vary depending on the type of each component, the blending ratio, etc., and can be set at 70° C. to 120° C. for about 1 minute to 10 minutes.
[步驟(2)] [step (2)]
本步驟中,對所形成的上述塗膜的至少一部分照射放射線來進行曝光。曝光時,通常隔著具有預定圖案的光罩進行曝光。用於曝光的放射線較佳為波長於190nm至450nm的範圍內的放射線,更佳為包含365nm的紫外線的放射線。曝光量是利用照度計(OAI model 356,OAI光學協會(OAI Optical Associates)製造)來測定放射線的波長365nm下 的強度而得的值,較佳為500J/m2至6,000J/m2,更佳為1,500J/m2至1,800J/m2。 In this step, exposure is performed by irradiating radiation to at least a part of the formed coating film. Exposure is usually performed through a photomask having a predetermined pattern. The radiation used for exposure is preferably radiation having a wavelength in the range of 190 nm to 450 nm, more preferably radiation including ultraviolet rays of 365 nm. The exposure amount is a value obtained by measuring the intensity of radiation at a wavelength of 365 nm with an illuminometer (OAI model 356, manufactured by OAI Optical Associates), and is preferably 500J/m 2 to 6,000J/m 2 , more preferably Preferably, it is 1,500J/m 2 to 1,800J/m 2 .
[步驟(3)] [step (3)]
本步驟中,對照射放射線後的上述塗膜進行顯影。藉由將曝光後的塗膜進行顯影,去除不需要的部分(放射線的照射部分),以形成預定的圖案。顯影步驟中使用的顯影液較佳為鹼性的水溶液。鹼例如可列舉:氫氧化鈉、氫氧化鉀、碳酸鈉、矽酸鈉、偏矽酸鈉、胺等無機鹼;四甲基氫氧化銨、四乙基氫氧化銨等四級銨鹽等。 In this step, the above-mentioned coating film irradiated with radiation is developed. By developing the exposed coating film, unnecessary parts (radiation irradiation parts) are removed to form a predetermined pattern. The developing solution used in the developing step is preferably an alkaline aqueous solution. Examples of the base include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, and amines; quaternary ammonium salts such as tetramethylammonium hydroxide and tetraethylammonium hydroxide; and the like.
鹼水溶液中,也可以適量添加甲醇、乙醇等水溶性有機溶劑或界面活性劑來使用。就獲得適當顯影性的觀點而言,鹼水溶液中的鹼的濃度較佳為0.1質量%以上、5質量%以下。顯影方法例如可列舉:覆液法(puddle method)、浸漬法、搖動浸漬法、噴淋法等。顯影時間根據化學增幅型正型感光性樹脂組成物的組成而有所不同,為10秒至180秒左右。在顯影處理之後,藉由進行例如流水清洗30秒至90秒,然後利用例如壓縮空氣或壓縮氮,風乾塗膜,以形成所需圖案。 The alkaline aqueous solution may be used by adding a suitable amount of a water-soluble organic solvent such as methanol or ethanol or a surfactant. From the viewpoint of obtaining appropriate developability, the concentration of the alkali in the aqueous alkali solution is preferably 0.1% by mass or more and 5% by mass or less. As an image development method, a puddle method, a dipping method, a shaking dipping method, a shower method, etc. are mentioned, for example. The developing time varies depending on the composition of the chemically amplified positive photosensitive resin composition, and is about 10 seconds to 180 seconds. After the developing process, the coating film is air-dried by running water for 30 seconds to 90 seconds, and then air-dried to form a desired pattern.
[步驟(4)] [step (4)]
本步驟中,將上述經顯影的塗膜進行加熱。加熱時,藉由使用加熱板、烘箱等加熱裝置,加熱圖案化的薄膜,以促進樹脂(A)的硬化反應,並獲得硬化物。加熱溫度例如為120℃至250℃左右。加熱時間根據加熱機器的種類而有所不同,例如在加熱板上為5分鐘至30分鐘左右,在烘箱中為30 分鐘至90分鐘左右。另外,也可以使用進行2次以上加熱步驟的階段式烘烤法等。如此一來,可將與做為目標的顯示元件用保護膜對應的圖案狀薄膜形成於基板的表面上。此外,上述硬化膜的用途並不限定於顯示元件用保護膜,也可以作為間隔件或層間絕緣膜來利用。 In this step, the above-mentioned developed coating film is heated. When heating, the patterned film is heated by using a heating device such as a heating plate or an oven to accelerate the curing reaction of the resin (A) and obtain a cured product. The heating temperature is, for example, about 120°C to 250°C. The heating time varies depending on the type of heating machine, for example, it is about 5 minutes to 30 minutes on a heating plate, and 30 minutes in an oven. minutes to about 90 minutes. In addition, a staged baking method in which a heating step is performed two or more times, etc. can also be used. In this way, a patterned thin film corresponding to the intended protective film for a display element can be formed on the surface of the substrate. In addition, the use of the said cured film is not limited to the protective film for display elements, It can also utilize it as a spacer or an interlayer insulating film.
所形成的顯示元件用保護膜的膜厚較佳為0.1μm至8μm,更佳為0.1μm至6μm,又更佳為0.1μm至4μm。 The film thickness of the formed protective film for display elements is preferably from 0.1 μm to 8 μm, more preferably from 0.1 μm to 6 μm, and still more preferably from 0.1 μm to 4 μm.
以下藉由數個製備例、實施例和比較例說明本發明的化學增幅型正型感光性樹脂組成物的製造方法及其應用。 The manufacturing method and application of the chemically amplified positive-type photosensitive resin composition of the present invention will be described below by means of several preparation examples, examples and comparative examples.
製備樹脂(A)Preparation of Resin (A)
製備例A-1Preparation Example A-1
在一容積1000毫升之四頸錐瓶上設置氮氣入口、攪拌器、加熱器、冷凝管及溫度計,導入氮氣後,添加5重量份之甲基丙烯酸(以下簡稱MAA)、20重量份的3-甲基丙烯醯氧基丙基三甲氧基矽烷(以下簡稱MAPTMS)、20重量份的2-四氫呋喃甲基丙烯酸酯、20重量份的甲基丙烯酸2-羥基乙酯(以下簡稱HEMA)、25重量份的甲基丙烯酸雙環戊酯(以下簡稱FA-513M)、10重量份的甲基丙烯酸苯甲 酯(以下簡稱BzMA)、10重量份的2,2’-偶氮雙(2,4-二甲基戊腈)(以下簡稱ADVN)以及240重量份的二乙二醇二甲醚(以下簡稱Diglyme)溶劑。接著,緩慢攪拌上述成份使溶液昇溫至70℃,並於此溫度下聚縮合6小時。然後,將溶劑脫揮後,可得樹脂(A-1)。 A nitrogen inlet, a stirrer, a heater, a condenser tube and a thermometer are arranged on a four-necked conical flask with a volume of 1000 milliliters. After introducing nitrogen, add 5 parts by weight of methacrylic acid (hereinafter referred to as MAA), 20 parts by weight of 3- Methacryloxypropyltrimethoxysilane (hereinafter referred to as MAPTMS), 20 parts by weight of 2-tetrahydrofuran methacrylate, 20 parts by weight of 2-hydroxyethyl methacrylate (hereinafter referred to as HEMA), 25 parts by weight Parts of dicyclopentyl methacrylate (hereinafter referred to as FA-513M), 10 parts by weight of benzyl methacrylate ester (hereinafter referred to as BzMA), 10 parts by weight of 2,2'-azobis(2,4-dimethylvaleronitrile) (hereinafter referred to as ADVN) and 240 parts by weight of diethylene glycol dimethyl ether (hereinafter referred to as Diglyme) solvent. Next, the above ingredients were stirred slowly to raise the temperature of the solution to 70° C., and polycondensed at this temperature for 6 hours. Then, after the solvent is devolatilized, resin (A-1) can be obtained.
製備例A-2至A-16以及製備比較例A’-1至A’-4Preparation Examples A-2 to A-16 and Preparation Comparative Examples A'-1 to A'-4
樹脂(A-2)至(A-16)及製備比較例(A’-1)至(A’-4)之製備與前述樹脂(A-1)之製備例類似,其中,單體之種類及使用量如表1所示。惟其中溶劑、觸媒之使用量、反應溫度及聚縮合之反應時間與前述樹脂(A-1)不同,亦示於表1。 The preparation of resins (A-2) to (A-16) and preparation comparative examples (A'-1) to (A'-4) is similar to the preparation of the aforementioned resin (A-1), wherein the type of monomer and usage are shown in Table 1. However, the amount of solvent and catalyst used, the reaction temperature and the reaction time of polycondensation are different from the aforementioned resin (A-1), which are also shown in Table 1.
實施例1Example 1
製備化學增幅型正型感光性樹脂組成物Preparation of chemically amplified positive photosensitive resin composition
將100重量份的樹脂(A-1)和0.1重量份的苄基(4-羥苯基)甲基硫鎓六氟銻酸鹽(B-1),加入200重量份的丙二醇甲醚醋酸酯(C-1)中,並以搖動式攪拌器(shaking type stirrer)攪拌均勻後,即可製得實施例1的化學增幅型正型感光性樹脂組成物。 With 100 parts by weight of resin (A-1) and 0.1 parts by weight of benzyl (4-hydroxyphenyl) methylsulfonium hexafluoroantimonate (B-1), add 200 parts by weight of propylene glycol methyl ether acetate (C-1), and after stirring evenly with a shaking type stirrer, the chemically amplified positive photosensitive resin composition of Example 1 can be obtained.
形成保護膜Form a protective film
於素玻璃基板(100×100×0.7mm)上,以旋轉塗佈方式得到約3μm之塗膜,接續以110℃預烤2分鐘後,在曝光機與塗膜間置入正光阻用光罩,並以曝光機之紫外光照射塗膜,其能量為80mJ/cm2。將曝光後的塗膜浸漬於23℃之2.38%之TMAH水溶液70秒,除去曝光之部分。以清 水清洗後,再以曝光機直接照射顯影後之塗膜,其能量為300mJ/cm2。最後以220℃後烤45分鐘,可獲得實施例1的素玻璃基板上之保護膜。 On a plain glass substrate (100×100×0.7mm), a coating film of about 3 μm was obtained by spin coating, followed by pre-baking at 110°C for 2 minutes, and a positive photoresist was placed between the exposure machine and the coating film Make a photomask, and irradiate the coating film with the ultraviolet light of the exposure machine, and the energy is 80mJ/cm 2 . Immerse the exposed coating film in 2.38% TMAH aqueous solution at 23°C for 70 seconds to remove the exposed part. After washing with clean water, the developed coating film is directly irradiated with an exposure machine with an energy of 300mJ/cm 2 . Finally, after baking at 220°C for 45 minutes, the protective film on the plain glass substrate of Example 1 can be obtained.
關於實施例1的具體條件以及評價結果,悉如表2所示。 About the concrete condition of embodiment 1 and evaluation result, note as shown in table 2.
實施例2至16及比較例1至4Examples 2 to 16 and Comparative Examples 1 to 4
實施例2至16及比較例1至4的化學增幅型正型感光性樹脂組成物及保護膜是使用與實施例1相同的方式進行而得。不同的是,實施例2至16及比較例1至4改變組成或使用量等條件。關於實施例2至16及比較例1至4的具體條件及評價結果如表2和表3所示。 The chemically amplified positive photosensitive resin compositions and protective films of Examples 2 to 16 and Comparative Examples 1 to 4 were obtained in the same manner as in Example 1. The difference is that conditions such as composition or usage amount were changed in Examples 2 to 16 and Comparative Examples 1 to 4. The specific conditions and evaluation results of Examples 2 to 16 and Comparative Examples 1 to 4 are shown in Table 2 and Table 3.
評價方式Evaluation method
(1)顯影密著性: (1) Development adhesion:
以上述保護膜的形成方法,形成化學增幅型正型感光性樹脂組成物的塗膜後,隔著具有寬1μm至10μm的線與空間圖案的圖案光阻,利用水銀燈對所述塗膜照射80mJ/cm2的紫外線。接著,使用四甲基氫氧化銨2.38質量%水溶液,在25℃下進行70秒顯影處理後,以超純水進行1分鐘流水清洗。利用顯微鏡來觀察清洗後的寬1μm至10μm的線與空間圖案的剝離情況,作為顯影密著性的評價。 With the formation method of the above-mentioned protective film, after forming the coating film of the chemically amplified positive-type photosensitive resin composition, through a pattern photoresist having a line and space pattern with a width of 1 μm to 10 μm , the said The coating film was irradiated with ultraviolet rays of 80 mJ/cm 2 . Next, after developing at 25 degreeC for 70 second using the 2.38 mass % aqueous solution of tetramethylammonium hydroxide, it wash|cleaned with running water for 1 minute with ultrapure water. Use a microscope to observe the peeling of the line and space patterns with a width of 1 μm to 10 μm after cleaning, as an evaluation of the development adhesion.
◎:無圖案剝離 ◎: No pattern peeling
○:圖案少量剝離 ○: A small amount of pattern peeling off
△:圖案的一部分剝離 Δ: Part of the pattern peeled off
×:圖案的整個面剝離 ×: The entire surface of the pattern is peeled off
(2)耐化性: (2) Chemical resistance:
以上述保護膜的形成方法,形成化學增幅型正型感光性樹脂組成物的塗膜後,使用加溫至230℃的烘箱,煅燒所述塗膜30分鐘,形成硬化膜。使所述硬化膜在加溫至40℃的N-甲基吡咯烷酮溶劑中浸漬6分鐘,求出浸漬前後的膜厚變化率(%),作為耐化學品性的指標。 After forming a coating film of the chemically amplified positive-type photosensitive resin composition by the above method of forming a protective film, the coating film was fired for 30 minutes in an oven heated to 230° C. to form a cured film. The cured film was immersed in an N-methylpyrrolidone solvent heated to 40° C. for 6 minutes, and the film thickness change rate (%) before and after immersion was obtained as an index of chemical resistance.
◎:膜厚変化率<5% ◎: film thickness change rate <5%
○:5%≦膜厚変化率<10% ○: 5%≦film thickness change rate<10%
△:10%≦膜厚変化率<15% △: 10%≦film thickness change rate<15%
×:15%≦膜厚変化率 ×: 15%≦film thickness change rate
如表2所示,當合成化學增幅型正型感光性樹脂組成物的樹脂(A)之混合物中,包括不飽和羧酸單體(a-1)、含矽烷基之不飽和化合物(a-2)和含酸解離性基之單體(a-3)時,由化學增幅型正型感光性樹脂組成物形成的保護膜可具有良好的顯影密著性和耐化性。在某些實施例中,當此混合物進一步包括含環氧基之不飽和單體(a-4)時,且特別是具有氧雜環丁烷的不飽和單體,可進一步改善保護膜的顯影密著性。在又一些實施例中,當化學增幅型正型感光性樹脂組成物使用具有肟磺酸酯基的化合物之光酸產生劑(B)時,也可進一步改善保護膜的耐化性。 As shown in Table 2, when the mixture of resin (A) for synthesizing the chemically amplified positive photosensitive resin composition includes unsaturated carboxylic acid monomer (a-1), silyl-containing unsaturated compound (a- 2) and the acid-dissociable group-containing monomer (a-3), the protective film formed from the chemically amplified positive photosensitive resin composition can have good development adhesion and chemical resistance. In some embodiments, when the mixture further includes an epoxy group-containing unsaturated monomer (a-4), and especially an unsaturated monomer with oxetane, the development of the protective film can be further improved Adhesion. In some other embodiments, when the chemically amplified positive photosensitive resin composition uses a photoacid generator (B) having an oxime sulfonate group, the chemical resistance of the protective film can be further improved.
另一方面,如表3所示,倘若合成化學增幅型正型感光性樹脂組成物的樹脂(A)之混合物中,未使用含矽烷 基之不飽和化合物(a-2)及/或含酸解離性基之單體(a-3)時,所製得的保護膜的耐化性和顯影密著性都不佳。 On the other hand, as shown in Table 3, if no silane-containing When the unsaturated compound (a-2) and/or acid-dissociative group-containing monomer (a-3) is used, the chemical resistance and development adhesion of the protective film obtained are not good.
應用本發明的化學增幅型正型感光性樹脂組成物,藉由特定的單體合成之樹脂(A),可形成具有良好顯影密著性和耐化性的保護膜。此保護膜可例如用於顯示元件。 Using the chemically amplified positive photosensitive resin composition of the present invention, the resin (A) synthesized from a specific monomer can form a protective film with good development adhesion and chemical resistance. This protective film can be used, for example, for display elements.
雖然本發明已以實施方式揭露如上,然其並非用以限定本發明,在本發明所屬技術領域中任何具有通常知識者,在不脫離本發明之精神和範圍內,當可作各種之更動與潤飾,因此本發明之保護範圍當視後附之申請專利範圍所界定者為準。 Although the present invention has been disclosed above in terms of implementation, it is not intended to limit the present invention. Anyone with ordinary knowledge in the technical field of the present invention can make various modifications and changes without departing from the spirit and scope of the present invention. Therefore, the scope of protection of the present invention should be defined by the scope of the appended patent application.
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