JP5945296B2 - スペーサ形成用感光性樹脂組成物及びこれから製造されたスペーサ - Google Patents
スペーサ形成用感光性樹脂組成物及びこれから製造されたスペーサ Download PDFInfo
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- JP5945296B2 JP5945296B2 JP2014110243A JP2014110243A JP5945296B2 JP 5945296 B2 JP5945296 B2 JP 5945296B2 JP 2014110243 A JP2014110243 A JP 2014110243A JP 2014110243 A JP2014110243 A JP 2014110243A JP 5945296 B2 JP5945296 B2 JP 5945296B2
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- photosensitive resin
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- 125000006850 spacer group Chemical group 0.000 title claims description 64
- 239000011342 resin composition Substances 0.000 title claims description 51
- 230000015572 biosynthetic process Effects 0.000 title claims description 42
- -1 1-hydroxy-n-propyl group Chemical group 0.000 claims description 107
- 150000001875 compounds Chemical class 0.000 claims description 72
- 229920005989 resin Polymers 0.000 claims description 52
- 239000011347 resin Substances 0.000 claims description 52
- 239000000126 substance Substances 0.000 claims description 34
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 239000003999 initiator Substances 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- NCAVPEPBIJTYSO-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate;2-(oxiran-2-ylmethoxymethyl)oxirane Chemical compound C1OC1COCC1CO1.OCCCCOC(=O)C=C NCAVPEPBIJTYSO-UHFFFAOYSA-N 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 10
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 claims description 3
- OCIFJWVZZUDMRL-UHFFFAOYSA-N 6-hydroxyhexyl prop-2-enoate Chemical compound OCCCCCCOC(=O)C=C OCIFJWVZZUDMRL-UHFFFAOYSA-N 0.000 claims description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 29
- 238000003786 synthesis reaction Methods 0.000 description 24
- 238000011084 recovery Methods 0.000 description 18
- 239000000758 substrate Substances 0.000 description 17
- 239000002253 acid Substances 0.000 description 14
- 238000001723 curing Methods 0.000 description 14
- 125000003700 epoxy group Chemical group 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- 238000000576 coating method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 239000004793 Polystyrene Substances 0.000 description 12
- 238000009826 distribution Methods 0.000 description 12
- 229920002223 polystyrene Polymers 0.000 description 12
- 239000000178 monomer Substances 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 9
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 9
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000004593 Epoxy Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000006073 displacement reaction Methods 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000012986 chain transfer agent Substances 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
- 230000000977 initiatory effect Effects 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000011973 solid acid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 230000001186 cumulative effect Effects 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
- 239000011521 glass Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- 125000006353 oxyethylene group Chemical group 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000007142 ring opening reaction Methods 0.000 description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- IPTNXMGXEGQYSY-UHFFFAOYSA-N acetic acid;1-methoxybutan-1-ol Chemical compound CC(O)=O.CCCC(O)OC IPTNXMGXEGQYSY-UHFFFAOYSA-N 0.000 description 3
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 238000000206 photolithography Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- GBOJZXLCJZDBKO-UHFFFAOYSA-N 2-(2-chlorophenyl)-2-[2-(2-chlorophenyl)-4,5-diphenylimidazol-2-yl]-4,5-diphenylimidazole Chemical compound ClC1=CC=CC=C1C1(C2(N=C(C(=N2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C(=CC=CC=2)Cl)N=C(C=2C=CC=CC=2)C(C=2C=CC=CC=2)=N1 GBOJZXLCJZDBKO-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- BERJMFPEDDOMCI-UHFFFAOYSA-N 2-amino-2-methyl-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C1=CC(C(=O)C(C)(N)CC)=CC=C1N1CCOCC1 BERJMFPEDDOMCI-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- GTYRFVGHYNRSKT-UHFFFAOYSA-N 3-benzylpyrrole-2,5-dione Chemical compound O=C1NC(=O)C(CC=2C=CC=CC=2)=C1 GTYRFVGHYNRSKT-UHFFFAOYSA-N 0.000 description 2
- YDIYEOMDOWUDTJ-UHFFFAOYSA-M 4-(dimethylamino)benzoate Chemical compound CN(C)C1=CC=C(C([O-])=O)C=C1 YDIYEOMDOWUDTJ-UHFFFAOYSA-M 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- XFOFBPRPOAWWPA-UHFFFAOYSA-N 6-hydroxyhexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCO XFOFBPRPOAWWPA-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 0 CC1C(CO)C2[C@@](C3)C(C)C*3C2C1 Chemical compound CC1C(CO)C2[C@@](C3)C(C)C*3C2C1 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-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
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- 150000008062 acetophenones Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000004842 bisphenol F epoxy resin Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- BHXIWUJLHYHGSJ-UHFFFAOYSA-N ethyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OCC BHXIWUJLHYHGSJ-UHFFFAOYSA-N 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000012423 maintenance Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 description 2
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- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-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
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Liquid Crystal (AREA)
- Epoxy Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
アルカリ可溶性樹脂は、光や熱に対する反応性及びアルカリ溶解性を有し、本発明の組成物中の各成分に対する分散媒として作用する。
化学式3において、ヘテロ原子は特に限定されず、例えば、窒素、酸素、硫黄のうち少なくとも一種であってよい。
不飽和結合及びカルボキシ基を有する化合物としては、重合可能な不飽和二重結合を有するカルボン酸化合物であれば制限されず、具体的な例としては、不飽和モノカルボン酸や、不飽和ジカルボン酸又は不飽和トリカルボン酸のような分子中に2個以上のカルボキシ基を有する多価カルボン酸等が挙げられる。
本発明による化学式1及び2のうち少なくとも1種である化合物は、重合可能な不飽和結合と架橋密度を増加させるエポキシ基とを有する化合物である。
化学式3の化合物は、脂肪族エポキシ基を有する化合物である。脂肪族エポキシ基は、反応性が高く、本発明の感光性樹脂組成物を用いてスペーサを製造する工程中において、開環反応が進行して架橋密度が増大されることにより、スペーサの強度等の機械的特性を強化されることができる。
(A−2)から誘導される構成単位:10〜85モル%
(A−3)から誘導される構成単位:10〜85モル%
特に、構成単位の割合が以下の数値範囲であれば、より好ましい。
(A−2)から誘導される構成単位:15〜75モル%
(A−3)から誘導される構成単位:15〜75モル%
構成単位の割合が前記数値範囲であれば、現像性、耐溶媒性、耐熱性、及び機械強度の良好な感光性樹脂組成物の製造が可能になる。
本発明のスペーサ形成用感光性樹脂組成物に含まれる光重合性化合物は、光及び後述の光重合開始剤の作用により重合することができる化合物であって、単官能単量体、二官能単量体、その他の多官能単量体等が挙げられる。
光重合開始剤としては、当分野において一般的に用いられるものが制限なく適用されることができる。
溶媒は、当分野において通常用いられるものであれば、どのようなものであっても制限なく用いられることができる。
本発明による感光性樹脂組成物は、必要に応じて、充填剤、他の高分子化合物、硬化剤、レベリング剤、密着促進剤、酸化防止剤、紫外線吸収剤、凝集防止剤、連鎖移動剤等の添加剤を更に含むことができる。
本発明は、前述の感光性樹脂組成物を所定のパターンで形成した後、露光及び現像して形成されるスペーサ、並びにこれを備えた画像表示装置を提供する。
攪拌機、温度計、還流冷却管、滴下ロート、及び窒素導入管を備えたフラスコを準備し、その一方で、モノマー滴下ロートに、3,4−エポキシトリシクロデカン−8−イル(メタ)アクリレート(化学式1)と3,4−エポキシトリシクロデカン−9−イル(メタ)アクリレート(化学式2)との混合物(モル比50:50)を20質量部、4−ヒドロキシブチルアクリレートグリシジルエーテルを20質量部、メチルメタクリレートを50質量部、アクリル酸を40質量部、ビニルトルエンを70質量部、t−ブチルパーオキシ−2−エチルヘキサノエートを4質量部、プロピレングリコールモノメチルエーテルアセテート(PGMEA)を40質量部投入した後に撹拌混合して準備し、連鎖移動剤滴下槽に、n−ドデカンチオールを6質量部、PGMEAを24質量部投入して撹拌混合したものを準備した。次に、フラスコにPGMEAを395質量部加えてフラスコ内の雰囲気を空気から窒素に置換した後、撹拌しながらフラスコの温度を90℃まで昇温させた。次いで、モノマー及び連鎖移動剤を滴下ロートから滴下し始めた。滴下は、90℃を維持しながらそれぞれ2時間行い、1時間後、110℃に昇温して5時間維持し、固形分の酸価が75mgKOH/gである樹脂(A−a)を得た。GPCによって測定されたポリスチレン換算の重量平均分子量は17,000であり、分子量分布(Mw/Mn)は2.3であった。
攪拌機、温度計、還流冷却管、滴下ロート、及び窒素導入管を備えたフラスコを準備し、その一方で、モノマー滴下ロートに、3,4−エポキシトリシクロデカン−8−イル(メタ)アクリレートと3,4−エポキシトリシクロデカン−9−イル(メタ)アクリレートとの混合物(モル比50:50)を30質量部、4−ヒドロキシブチルアクリレートグリシジルエーテルを30質量部、メチルメタクリレートを50質量部、アクリル酸を40質量部、ベンジルマレイミドを50質量部、t−ブチルパーオキシ−2−エチルヘキサノエートを4質量部、プロピレングリコールモノメチルエーテルアセテートを40質量部投入した後に撹拌混合して準備し、連鎖移動剤滴下槽に、n−ドデカンチオールを6質量部、PGMEAを24質量部投入して撹拌混合したものを準備した。次に、フラスコにPGMEAを395質量部加えてフラスコ内の雰囲気を空気から窒素に置換した後、撹拌しながらフラスコの温度を90℃まで昇温させた。次いで、モノマー及び連鎖移動剤を滴下ロートから滴下し始めた。滴下は、90℃を維持しながらそれぞれ2時間行い、1時間後、110℃に昇温して5時間維持し、固形分の酸価が73mgKOH/gである樹脂(A−b)を得た。GPCによって測定されたポリスチレン換算の重量平均分子量は18,000であり、分子量分布(Mw/Mn)は2.2であった。
4−ヒドロキシブチルアクリレートグリシジルエーテルに代えて2−プロペン酸4−(4−オキシラニルブトキシ)ブチルエーテルを添加したこと以外は合成例1と同様に行い、固形分の酸価が72mgKOH/gである樹脂(A−c)を得た。GPCによって測定されたポリスチレン換算の重量平均分子量は16,700であり、分子量分布(Mw/Mn)は2.2であった。
4−ヒドロキシブチルアクリレートグリシジルエーテルに代えて6−ヒドロキシヘキシルアクリレートグリシジルエーテルを添加したこと以外は合成例1と同様に行い、固形分の酸価が73mgKOH/gである樹脂(A−d)を得た。GPCによって測定されたポリスチレン換算の重量平均分子量は16,500であり、分子量分布(Mw/Mn)は2.2であった。
4−ヒドロキシブチルアクリレートグリシジルエーテルに代えて2−エチル−3−オキセタニルメチルメタクリレートを添加したこと以外は合成例1と同様に行い、固形分の酸価が73mgKOH/gである樹脂(A−e)を得た。GPCによって測定されたポリスチレン換算の重量平均分子量は16,500であり、分子量分布(Mw/Mn)は2.1であった。
4−ヒドロキシブチルアクリレートグリシジルエーテルに代えてグリシジルメタクリレートを添加したこと以外は合成例1と同様に行い、固形分の酸価が74mgKOH/gである樹脂(A−f)を得た。GPCによって測定されたポリスチレン換算の重量平均分子量は17,300であり、分子量分布(Mw/Mn)は2.3であった。
4−ヒドロキシブチルアクリレートグリシジルエーテルを添加せずに、3,4−エポキシトリシクロデカン−8−イル(メタ)アクリレート(化学式1)と3,4−エポキシトリシクロデカン−9−イル(メタ)アクリレート(化学式2)との混合物(モル比50:50)を40質量部用いたこと以外は合成例1と同様に行い、固形分の酸価が73mgKOH/gである樹脂(A−g)を得た。GPCによって測定されたポリスチレン換算の重量平均分子量は18,200であり、分子量分布(Mw/Mn)は2.2であった。
4−ヒドロキシブチルアクリレートグリシジルエーテルを添加せず、3,4−エポキシトリシクロデカン−8−イル(メタ)アクリレート(化学式1)と3,4−エポキシトリシクロデカン−9−イル(メタ)アクリレート(化学式2)との混合物(モル比50:50)を60質量部用いたこと以外は合成例2と同様に行い、固形分の酸価が73mgKOH/gである樹脂(A−h)を得た。GPCによって測定されたポリスチレン換算の重量平均分子量は18,000であり、分子量分布(Mw/Mn)は2.4であった。
4−ヒドロキシブチルアクリレートグリシジルエーテルに代えて3,4−エポキシシクロヘキシル(メタ)アクリレートを添加したこと以外は合成例1と同様に行い、固形分の酸価が74mgKOH/gである樹脂(A−i)を得た。GPCによって測定されたポリスチレン換算の重量平均分子量は17,800であり、分子量分布(Mw/Mn)は2.3であった。
カラム:TSK−GELG4000HXL+TSK−GELG2000HXL(直列接続)
カラム温度:40℃
移動相溶媒:テトラヒドロフラン
流速:1.0mL/分
注入量:50μL
検出機:RI
測定試料濃度:0.6質量%(溶媒=テトラヒドロフラン)
校正用標準物質:TSK STANDARD POLYSTYRENE F−40、F−4、F−1、A−2500、A−500(東ソー(株)製)
前記で得られた重量平均分子量及び数平均分子量の比を分子量分布(Mw/Mn)とした。
下記表1に記載の成分及び組成からスペーサ形成用感光性樹脂組成物を調製した(単位は質量部)。
横及び縦の長さが2インチのガラス基板(イーグル2000;コーニング社製)を中性洗剤、水、及びアルコールで順次洗浄した後、乾燥させた。このガラス基板上に、実施例及び比較例において調製した感光性樹脂組成物をそれぞれスピンコーティングした後、クリーンオーブン中において90℃で3分間プリベークした。前記プリベークした基板を常温に冷却させた後、石英ガラス製フォトマスクとの間隔を150μmにして、露光機(TME−150RSK;トプコン(株)製)を用いて60mJ/cm2の露光量(405nm基準)で光を照射した。この時の重合性樹脂組成物への照射は、超高圧水銀灯からの放射光を、光学フィルタ(LU0400;朝日分光(株)製)を通過させた後、400nm以下の光をカットして用いた。この時、フォトマスクとして、次のパターンが同一平面上に形成されたフォトマスクが用いられた。
前記で得られた膜厚3.0μmにおけるパターンサイズを三次元形状測定装置(SIS−2000 System;SNU Precision社製)を用いて測定し、マスクサイズとの差をCD−biasで下記のとおり算出する。CD−biasは、0に近接する程良好であり、(+)は、パターンがマスクよりサイズが大きいことを、(−)は、マスクよりサイズが小さいことを意味する。
前記で得られた硬化膜を走査型電子顕微鏡(S−4600;(株)日立製作所製)を用いてマスク14μmによって形成されたパターンの線幅を測定し、断面形状を下記のように評価した。断面形状は、基板に対するパターンの角度が90度未満であれば順テーパであり、90度以上であれば逆テーパであると判断した。
前記で得られた硬化膜をダイナミック超微小硬度計(HM−2000;Helmut Fischer GmbH+Co.KG)を用いて、その総変位量(μm)及び弾性変位量(μm)を下記の測定条件によって測定し、測定された数値を用いて下記のように回復率(%)を算出した。総変位量が少なく、且つ回復率が大きければ硬いと判断した。
測定条件は下記のとおりである。
試験力:50.0mN
負荷速度:4.41mN/sec
維持時間:5sec
圧子:四角錐台圧子(直径50μm)
前記で得られた硬化膜をダイナミック超微小硬度計(HM−2000;Helmut Fischer GmbH+Co.KG)を用いて、同一のパターンを下記の条件に従って10回繰り返し荷重を与え、荷重を与えた前/後のパターン高さの変化量を三次元形状測定装置(SIS−2000 System;SUN Precision社製)を用いて測定する。
試験力:50.0mN
負荷速度:4.41mN/sec
維持時間:5sec
圧子:四角錐台圧子(直径50μm)
回数:10回
現像密着性は、直径(size)が5μmから20μmまで1μm間隔の円型パターンをそれぞれ1000個有するフォトマスクによって、膜厚が3μmで形成されたパターンが欠落なく100%残存するマスクのサイズを顕微鏡によって評価した。マスクのサイズが小さい程、感度に優れる。
Claims (7)
- アルカリ可溶性樹脂と、光重合性化合物と、光重合開始剤と、溶媒とを含む感光性樹脂組成物であって、
前記アルカリ可溶性樹脂は、(A−1)不飽和結合及びカルボキシ基を有する化合物から誘導される構成単位と、(A−2)下記化学式1及び2のうち少なくとも1種である化合物から誘導される構成単位と、(A−3)下記化学式3の化合物から誘導される構成単位とを含む共重合体である、スペーサ形成用感光性樹脂組成物。
〔式中、R1は、水素、或いは、ヘテロ原子を有するか若しくは有しない炭素数1〜20のアルキル又はシクロアルキルであり;R2は、単結合、或いは、ヘテロ原子を有するか若しくは有しない炭素数1〜20のアルキレン又はシクロアルキレンであり;前記R1及びR2は、それぞれ独立して、ヒドロキシ基で置換されてもよい。〕
〔式中、R1は、水素、或いは、ヘテロ原子を有するか若しくは有しない炭素数1〜20のアルキル又はシクロアルキルであり;R2は、単結合、或いは、ヘテロ原子を有するか若しくは有しない炭素数1〜20のアルキレン又はシクロアルキレンであり;前記R1及びR2は、それぞれ独立して、ヒドロキシ基で置換されてもよい。〕
〔式中、R1は、水素、炭素数1〜10のアルキル又は炭素数3〜10のシクロアルキルであり、前記アルキル及びシクロアルキルは、それぞれ独立して、ヘテロ原子を有してもよく;R2及びR3は、それぞれ独立して、炭素数1〜20の直鎖又は分岐鎖のアルキレンであり;前記R1、R2、及びR3は、それぞれ独立して、ヒドロキシ基で更に置換されてもよい。〕 - 前記化学式3のR1は、水素、メチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、sec−ブチル基、tert−ブチル基、ヒドロキシメチル基、1−ヒドロキシエチル基、2−ヒドロキシエチル基、1−ヒドロキシ−n−プロピル基、2−ヒドロキシ−n−プロピル基、3−ヒドロキシ−n−プロピル基、1−ヒドロキシイソプロピル基、2−ヒドロキシイソプロピル基、1−ヒドロキシ−n−ブチル基、2−ヒドロキシ−n−ブチル基、3−ヒドロキシ−n−ブチル基、及び4−ヒドロキシ−n−ブチル基からなる群から選択されるいずれか一種である、請求項1に記載のスペーサ形成用感光性樹脂組成物。
- 前記化学式3のR2及びR3は、それぞれ独立して、メチレン基、エチレン基、プロピレン基、ブチレン基、テトラメチレン基、エチルエチレン基、及びペンタメチレン基からなる群から選択されるいずれか一種である、請求項1に記載のスペーサ形成用感光性樹脂組成物。
- 前記(A−3)化合物は、2−ヒドロキシエチルアクリレートグリシジルエーテル;2−ヒドロキシエチルメタクリレートグリシジルエーテル;4−ヒドロキシブチルアクリレートグリシジルエーテル;4−ヒドロキシブチルメタクリレートグリシジルエーテル;6−ヒドロキシヘキシルアクリレートグリシジルエーテル;6−ヒドロキシヘキシルメタクリレートグリシジルエーテル;2-プロペン酸2‐(2‐オキシラン-2-イル)エトキシ)エチル、及び2−プロペン酸4−(4−オキシラン−2−イル)ブトキシ)ブチルからなる群から選択される少なくとも一種である、請求項1に記載のスペーサ形成用感光性樹脂組成物。
- 前記アルカリ可溶性樹脂は、(A−1)化合物から誘導される構成単位を5〜80モル%と、(A−2)化合物から誘導される構成単位を10〜85モル%と、(A−3)化合物から誘導される構成単位を10〜85モル%とを含む、請求項1に記載のスペーサ形成用感光性樹脂組成物。
- 請求項1〜5のいずれか一項に記載のスペーサ形成用感光性樹脂組成物から製造されたスペーサ。
- 請求項6に記載のスペーサを備える画像表示装置。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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