JP2012168289A - Positive radiation-sensitive resin composition, interlayer insulating film for display element, and formation method thereof - Google Patents
Positive radiation-sensitive resin composition, interlayer insulating film for display element, and formation method thereof Download PDFInfo
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- JP2012168289A JP2012168289A JP2011027834A JP2011027834A JP2012168289A JP 2012168289 A JP2012168289 A JP 2012168289A JP 2011027834 A JP2011027834 A JP 2011027834A JP 2011027834 A JP2011027834 A JP 2011027834A JP 2012168289 A JP2012168289 A JP 2012168289A
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- Prior art keywords
- resin composition
- sensitive resin
- mass
- mol
- polyorganosiloxane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 230000005855 radiation Effects 0.000 title claims abstract description 148
- 239000011342 resin composition Substances 0.000 title claims abstract description 82
- 239000011229 interlayer Substances 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 32
- 230000015572 biosynthetic process Effects 0.000 title abstract description 22
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 35
- 125000000962 organic group Chemical group 0.000 claims abstract description 23
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 150000001721 carbon Chemical group 0.000 claims abstract 2
- -1 quinonediazide compound Chemical class 0.000 claims description 75
- 238000000576 coating method Methods 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 38
- 239000011248 coating agent Substances 0.000 claims description 38
- 238000010438 heat treatment Methods 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 18
- 230000001678 irradiating effect Effects 0.000 claims description 7
- 239000002904 solvent Substances 0.000 abstract description 46
- 230000035945 sensitivity Effects 0.000 abstract description 14
- 150000001875 compounds Chemical class 0.000 description 23
- 239000000243 solution Substances 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 20
- 238000003786 synthesis reaction Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 230000007062 hydrolysis Effects 0.000 description 16
- 238000006460 hydrolysis reaction Methods 0.000 description 16
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
- 239000004094 surface-active agent Substances 0.000 description 15
- 238000010521 absorption reaction Methods 0.000 description 14
- 239000004973 liquid crystal related substance Substances 0.000 description 14
- 238000011161 development Methods 0.000 description 13
- 230000018109 developmental process Effects 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000007859 condensation product Substances 0.000 description 12
- 239000000155 melt Substances 0.000 description 12
- 229910000077 silane Inorganic materials 0.000 description 12
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000012024 dehydrating agents Substances 0.000 description 8
- 150000007530 organic bases Chemical class 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 8
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 7
- 238000006482 condensation reaction Methods 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 150000004756 silanes Chemical class 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 6
- 239000010452 phosphate Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 230000007261 regionalization Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 6
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- 150000001339 alkali metal compounds Chemical class 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 210000002858 crystal cell Anatomy 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 235000006408 oxalic acid Nutrition 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 4
- ZYVXFNCWRJNIQJ-UHFFFAOYSA-M 1-(4,7-dibutoxynaphthalen-1-yl)thiolan-1-ium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C12=CC(OCCCC)=CC=C2C(OCCCC)=CC=C1[S+]1CCCC1 ZYVXFNCWRJNIQJ-UHFFFAOYSA-M 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 description 3
- WXYSZTISEJBRHW-UHFFFAOYSA-N 4-[2-[4-[1,1-bis(4-hydroxyphenyl)ethyl]phenyl]propan-2-yl]phenol Chemical compound C=1C=C(C(C)(C=2C=CC(O)=CC=2)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WXYSZTISEJBRHW-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- OWZDULOODZHVCQ-UHFFFAOYSA-N diphenyl-(4-phenylsulfanylphenyl)sulfanium Chemical compound C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 OWZDULOODZHVCQ-UHFFFAOYSA-N 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000009413 insulation Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 2
- 229940105324 1,2-naphthoquinone Drugs 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- GYQQFWWMZYBCIB-UHFFFAOYSA-N 1-[diazo-(4-methylphenyl)sulfonylmethyl]sulfonyl-4-methylbenzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1=CC=C(C)C=C1 GYQQFWWMZYBCIB-UHFFFAOYSA-N 0.000 description 2
- OJVAMHKKJGICOG-UHFFFAOYSA-N 2,5-hexanedione Chemical compound CC(=O)CCC(C)=O OJVAMHKKJGICOG-UHFFFAOYSA-N 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 2
- XDQWJFXZTAWJST-UHFFFAOYSA-N 3-triethoxysilylpropyl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C=C XDQWJFXZTAWJST-UHFFFAOYSA-N 0.000 description 2
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 2
- DOTXUIUDUBARJK-UHFFFAOYSA-N 4-(thiolan-1-ium-1-yl)naphthalene-1,6-diol;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C12=CC(O)=CC=C2C(O)=CC=C1[S+]1CCCC1 DOTXUIUDUBARJK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- GLGXSTXZLFQYKJ-UHFFFAOYSA-N [cyclohexylsulfonyl(diazo)methyl]sulfonylcyclohexane Chemical compound C1CCCCC1S(=O)(=O)C(=[N+]=[N-])S(=O)(=O)C1CCCCC1 GLGXSTXZLFQYKJ-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 2
- IWSWFHYTNFXRBK-UHFFFAOYSA-N diphenyl-(4-phenylphenyl)sulfanium Chemical compound C1=CC=CC=C1[S+](C=1C=CC(=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IWSWFHYTNFXRBK-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 2
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 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
- 230000001771 impaired effect Effects 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 2
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 2
- XSIGLRIVXRKQRA-UHFFFAOYSA-N triethoxysilylmethanethiol Chemical compound CCO[Si](CS)(OCC)OCC XSIGLRIVXRKQRA-UHFFFAOYSA-N 0.000 description 2
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- SLWJCUBAEHHRME-UHFFFAOYSA-N tri(butan-2-yloxy)-(3,3,3-trifluoropropyl)silane Chemical compound CCC(C)O[Si](CCC(F)(F)F)(OC(C)CC)OC(C)CC SLWJCUBAEHHRME-UHFFFAOYSA-N 0.000 description 1
- NZUZSTKWRHPHIS-UHFFFAOYSA-N tri(butan-2-yloxy)-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F NZUZSTKWRHPHIS-UHFFFAOYSA-N 0.000 description 1
- RTMADTFOHZKQTE-UHFFFAOYSA-N tri(butan-2-yloxy)-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)silane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RTMADTFOHZKQTE-UHFFFAOYSA-N 0.000 description 1
- MHQDJCZAQGWXBC-UHFFFAOYSA-N tri(butan-2-yloxy)-ethenylsilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C=C MHQDJCZAQGWXBC-UHFFFAOYSA-N 0.000 description 1
- RJNDDRZGJNVASH-UHFFFAOYSA-N tri(butan-2-yloxy)-methylsilane Chemical compound CCC(C)O[Si](C)(OC(C)CC)OC(C)CC RJNDDRZGJNVASH-UHFFFAOYSA-N 0.000 description 1
- PCDRXIBYKFIRQR-UHFFFAOYSA-N tri(butan-2-yloxy)-phenylsilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C1=CC=CC=C1 PCDRXIBYKFIRQR-UHFFFAOYSA-N 0.000 description 1
- COKLPZSYWJNYBJ-UHFFFAOYSA-N tri(butan-2-yloxy)silane Chemical compound CCC(C)O[SiH](OC(C)CC)OC(C)CC COKLPZSYWJNYBJ-UHFFFAOYSA-N 0.000 description 1
- HMAGLHWOMNVLHF-UHFFFAOYSA-N tri(butan-2-yloxy)silylmethanol Chemical compound CCC(C)O[Si](CO)(OC(C)CC)OC(C)CC HMAGLHWOMNVLHF-UHFFFAOYSA-N 0.000 description 1
- MLURNIQQAGXMGF-UHFFFAOYSA-N tributoxy(3,3,3-trifluoropropyl)silane Chemical compound CCCCO[Si](CCC(F)(F)F)(OCCCC)OCCCC MLURNIQQAGXMGF-UHFFFAOYSA-N 0.000 description 1
- MGYAETYXWNGOHQ-UHFFFAOYSA-N tributoxy(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F MGYAETYXWNGOHQ-UHFFFAOYSA-N 0.000 description 1
- GIHPVQDFBJMUAO-UHFFFAOYSA-N tributoxy(ethyl)silane Chemical compound CCCCO[Si](CC)(OCCCC)OCCCC GIHPVQDFBJMUAO-UHFFFAOYSA-N 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- INUOIYMEJLOQFN-UHFFFAOYSA-N tributoxy(phenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC=C1 INUOIYMEJLOQFN-UHFFFAOYSA-N 0.000 description 1
- UCSBCWBHZLSFGC-UHFFFAOYSA-N tributoxysilane Chemical compound CCCCO[SiH](OCCCC)OCCCC UCSBCWBHZLSFGC-UHFFFAOYSA-N 0.000 description 1
- KLUPBUUXPVHSRA-UHFFFAOYSA-N tributoxysilylmethanol Chemical compound CCCCO[Si](CO)(OCCCC)OCCCC KLUPBUUXPVHSRA-UHFFFAOYSA-N 0.000 description 1
- ZYNNGMKJWXEYBV-UHFFFAOYSA-N tributylsilyl acetate Chemical compound CCCC[Si](CCCC)(CCCC)OC(C)=O ZYNNGMKJWXEYBV-UHFFFAOYSA-N 0.000 description 1
- WEUBQNJHVBMUMD-UHFFFAOYSA-N trichloro(3,3,3-trifluoropropyl)silane Chemical compound FC(F)(F)CC[Si](Cl)(Cl)Cl WEUBQNJHVBMUMD-UHFFFAOYSA-N 0.000 description 1
- PISDRBMXQBSCIP-UHFFFAOYSA-N trichloro(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CC[Si](Cl)(Cl)Cl PISDRBMXQBSCIP-UHFFFAOYSA-N 0.000 description 1
- VIFIHLXNOOCGLJ-UHFFFAOYSA-N trichloro(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)silane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)CC[Si](Cl)(Cl)Cl VIFIHLXNOOCGLJ-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- PGHWHQUVLXTFLZ-UHFFFAOYSA-N trichloro(fluoro)silane Chemical compound F[Si](Cl)(Cl)Cl PGHWHQUVLXTFLZ-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- HKFSBKQQYCMCKO-UHFFFAOYSA-N trichloro(prop-2-enyl)silane Chemical compound Cl[Si](Cl)(Cl)CC=C HKFSBKQQYCMCKO-UHFFFAOYSA-N 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- TVJIJCPNBAPRRJ-UHFFFAOYSA-N trichlorosilylmethanol Chemical compound OC[Si](Cl)(Cl)Cl TVJIJCPNBAPRRJ-UHFFFAOYSA-N 0.000 description 1
- AVYKQOAMZCAHRG-UHFFFAOYSA-N triethoxy(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F AVYKQOAMZCAHRG-UHFFFAOYSA-N 0.000 description 1
- MLXDKRSDUJLNAB-UHFFFAOYSA-N triethoxy(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F MLXDKRSDUJLNAB-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- XVYIJOWQJOQFBG-UHFFFAOYSA-N triethoxy(fluoro)silane Chemical compound CCO[Si](F)(OCC)OCC XVYIJOWQJOQFBG-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- QJOOZNCPHALTKK-UHFFFAOYSA-N trimethoxysilylmethanethiol Chemical compound CO[Si](CS)(OC)OC QJOOZNCPHALTKK-UHFFFAOYSA-N 0.000 description 1
- SPHALHRGAQVBKI-UHFFFAOYSA-N trimethoxysilylmethanol Chemical compound CO[Si](CO)(OC)OC SPHALHRGAQVBKI-UHFFFAOYSA-N 0.000 description 1
- PHPGKIATZDCVHL-UHFFFAOYSA-N trimethyl(propoxy)silane Chemical compound CCCO[Si](C)(C)C PHPGKIATZDCVHL-UHFFFAOYSA-N 0.000 description 1
- PGZGBYCKAOEPQZ-UHFFFAOYSA-N trimethyl-[(2-methylpropan-2-yl)oxy]silane Chemical compound CC(C)(C)O[Si](C)(C)C PGZGBYCKAOEPQZ-UHFFFAOYSA-N 0.000 description 1
- QHUNJMXHQHHWQP-UHFFFAOYSA-N trimethylsilyl acetate Chemical compound CC(=O)O[Si](C)(C)C QHUNJMXHQHHWQP-UHFFFAOYSA-N 0.000 description 1
- KBPSATXXRVXAAJ-UHFFFAOYSA-N trimethylsilyl formate Chemical compound C[Si](C)(C)OC=O KBPSATXXRVXAAJ-UHFFFAOYSA-N 0.000 description 1
- ZVPKMEQEIHFILG-UHFFFAOYSA-N tripropoxy(3,3,3-trifluoropropyl)silane Chemical compound CCCO[Si](CCC(F)(F)F)(OCCC)OCCC ZVPKMEQEIHFILG-UHFFFAOYSA-N 0.000 description 1
- UVGGWQBDKIBLIU-UHFFFAOYSA-N tripropoxy(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl)silane Chemical compound CCCO[Si](OCCC)(OCCC)CCC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F UVGGWQBDKIBLIU-UHFFFAOYSA-N 0.000 description 1
- OZWKZRFXJPGDFM-UHFFFAOYSA-N tripropoxysilane Chemical compound CCCO[SiH](OCCC)OCCC OZWKZRFXJPGDFM-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
Abstract
Description
本発明は、ポジ型感放射線性樹脂組成物、表示素子用層間絶縁膜及びその形成方法に関する。 The present invention relates to a positive radiation sensitive resin composition, an interlayer insulating film for a display element, and a method for forming the same.
液晶表示素子等には、一般に層状に配置される配線の間を絶縁するために層間絶縁膜が設けられている。層間絶縁膜の形成材料としては、必要とするパターン形状を得るための工程数を少なくでき、かつ十分な平坦性を有する材料が好ましいことから、感放射線性樹脂組成物が幅広く使用されている。 A liquid crystal display element or the like is generally provided with an interlayer insulating film in order to insulate between wirings arranged in layers. As a material for forming an interlayer insulating film, a radiation-sensitive resin composition is widely used because a material that can reduce the number of steps for obtaining a required pattern shape and has sufficient flatness is preferable.
また、液晶表示素子の層間絶縁膜は、配線用コンタクトホールパターンの形成が必要であるところ、ネガ型感放射線性樹脂組成物では実用上使用できるレベルのホール径を有するパターン形成が困難であることから、ポジ型感放射線性樹脂組成物が幅広く使用されている(特開2001−354822号公報参照)。かかるポジ型感放射線性樹脂組成物の主成分としては、通常アクリル系樹脂が使用されるが、透明性に優れるポリシロキサン系材料を主成分として用いる試みもなされている(特開2000−1648号公報及び特開2006−178436号公報参照)。 In addition, the interlayer insulating film of the liquid crystal display element needs to form a contact hole pattern for wiring. However, it is difficult to form a pattern having a hole diameter of a practically usable level with a negative radiation sensitive resin composition. Therefore, positive radiation sensitive resin compositions are widely used (see JP 2001-354822 A). As the main component of such a positive radiation sensitive resin composition, an acrylic resin is usually used. However, attempts have been made to use a polysiloxane material having excellent transparency as a main component (Japanese Patent Laid-Open No. 2000-1648). Gazette and JP-A-2006-178436).
一方、液晶表示素子の表示不良を防止する観点から、層間絶縁膜にはポストベーク工程におけるパターンの耐メルトフロー性、ポストベーク工程後の耐溶媒性及び耐熱性が必要とされる。しかしながら、従来のポリシロキサン系材料を主成分とするポジ型感放射線性樹脂組成物は、層間絶縁膜の形成材料として求められる耐メルトフロー性、耐熱性及び耐溶媒性を十分に満足するものではない。 On the other hand, from the viewpoint of preventing display defects of the liquid crystal display element, the interlayer insulating film is required to have a pattern melt-flow resistance in the post-baking process, solvent resistance and heat resistance after the post-baking process. However, conventional positive-type radiation-sensitive resin compositions mainly composed of polysiloxane materials do not sufficiently satisfy the melt flow resistance, heat resistance, and solvent resistance required as materials for forming interlayer insulating films. Absent.
このような状況において、現像後の加熱工程における耐メルトフロー性、加熱工程後の耐溶媒性及び耐熱性に優れ、かつ十分な感度を有するポリシロキサン系ポジ型感放射線性樹脂組成物の開発が強く望まれている。 Under such circumstances, development of a polysiloxane-based positive radiation sensitive resin composition having excellent melt flow resistance in the heating step after development, solvent resistance and heat resistance after the heating step, and sufficient sensitivity has been developed. It is strongly desired.
本発明は、以上のような事情に基づいてなされたものであり、その目的は十分な感度を有するポジ型感放射線性樹脂組成物、並びにこのポジ型感放射線性樹脂組成物を用い、優れた耐メルトフロー性、耐熱性及び耐溶媒性を有し、電圧保持率に優れる層間絶縁膜及びその形成方法を提供することである。 The present invention has been made on the basis of the circumstances as described above, and the object thereof is to use a positive radiation sensitive resin composition having sufficient sensitivity, and to use this positive radiation sensitive resin composition. An object of the present invention is to provide an interlayer insulating film having melt flow resistance, heat resistance and solvent resistance and excellent voltage holding ratio, and a method for forming the interlayer insulating film.
上記課題を解決するためになされた発明は、
[A1]ケイ素原子に炭素原子で結合する有機基のうち、エポキシ基を有する有機基の含有割合が、0モル%以上50モル%未満であるポリオルガノシロキサン(以下、「[A1]ポリオルガノシロキサン」とも称する)、
、及び
[A2]上記含有割合が、50モル%以上100モル%以下であるポリオルガノシロキサン(以下、「[A2]ポリオルガノシロキサン」とも称する)
を含有するポジ型感放射線性樹脂組成物である。
The invention made to solve the above problems is
[A1] A polyorganosiloxane having an epoxy group-containing organic group content of organic groups bonded to silicon atoms by carbon atoms (hereinafter referred to as “[A1] polyorganosiloxane”). ”),
And [A2] a polyorganosiloxane having the above content ratio of 50 mol% or more and 100 mol% or less (hereinafter also referred to as “[A2] polyorganosiloxane”)
Is a positive-type radiation-sensitive resin composition.
当該ポジ型感放射線性樹脂組成物が、[A1]ポリオルガノシロキサン及び[A2]ポリオルガノシロキサン(以下、これら2成分を合わせて「[A]ポリオルガノシロキサン」とも称する)を含有し、エポキシ基を有する有機基の含有割合を上記特定範囲とすることで、現像後の加熱工程における耐メルトフロー性、加熱工程後の耐溶媒性及び耐熱性に優れる層間絶縁膜を形成でき、かつ十分な感度を発現することができる。 The positive-type radiation-sensitive resin composition contains [A1] polyorganosiloxane and [A2] polyorganosiloxane (hereinafter, these two components are collectively referred to as “[A] polyorganosiloxane”), and an epoxy group By making the content ratio of the organic group having the above specified range, an interlayer insulating film excellent in melt flow resistance in the heating step after development, solvent resistance and heat resistance after the heating step can be formed, and sufficient sensitivity Can be expressed.
上記エポキシ基を有する有機基は、下記式(1)及び式(2)で表される基からなる群より選択される少なくとも1種であることが好ましい。
[A1]ポリオルガノシロキサン及び[A2]ポリオルガノシロキサン中のエポキシ基を上記特定基とすることで、耐メルトフロー性、耐溶媒性及び耐熱性をより向上させることができる。 By making the epoxy group in [A1] polyorganosiloxane and [A2] polyorganosiloxane the above-mentioned specific group, the melt flow resistance, solvent resistance and heat resistance can be further improved.
[A2]ポリオルガノシロキサンの含有量は、[A1]ポリオルガノシロキサン100質量部に対して、20質量部以下であることが好ましい。[A2]ポリオルガノシロキサンの含有量を、上記特定量とすることで耐メルトフロー性、耐溶媒性及び耐熱性をより向上させることができる。 [A2] The content of polyorganosiloxane is preferably 20 parts by mass or less with respect to 100 parts by mass of [A1] polyorganosiloxane. [A2] Melt flow resistance, solvent resistance, and heat resistance can be further improved by setting the content of the polyorganosiloxane to the above specific amount.
[A1]ポリオルガノシロキサンにおけるエポキシ基を有する有機基の含有割合が、0モル%以上5モル%以下であり、かつ[A2]ポリオルガノシロキサンにおけるエポキシ基を有する有機基の含有割合が、95%以上100モル%以下であることが好ましい。[A1]ポリオルガノシロキサン及び[A2]ポリオルガノシロキサン中のエポキシ基を有する有機基の含有割合を上記特定範囲とすることで、耐メルトフロー性、耐溶媒性及び耐熱性を特に向上させることができる。 [A1] The content ratio of the organic group having an epoxy group in the polyorganosiloxane is 0 mol% or more and 5 mol% or less, and the content ratio of the organic group having an epoxy group in the [A2] polyorganosiloxane is 95%. It is preferable that it is 100 mol% or less. By making the content ratio of the organic group having an epoxy group in [A1] polyorganosiloxane and [A2] polyorganosiloxane within the above specified range, the melt flow resistance, solvent resistance and heat resistance can be particularly improved. it can.
当該ポジ型感放射線性樹脂組成物は、[B]キノンジアジド化合物をさらに含有することが好ましい。当該ポジ型感放射線性樹脂組成物が[B]キノンジアジド化合物をさらに含有することで、露光された部分が現像工程により除去されるポジ型の感放射線特性を当該ポジ型感放射線性樹脂組成物に付与することができる。 The positive radiation sensitive resin composition preferably further contains a [B] quinonediazide compound. When the positive radiation sensitive resin composition further contains a [B] quinonediazide compound, the positive radiation sensitive characteristic in which the exposed portion is removed by the development process is added to the positive radiation sensitive resin composition. Can be granted.
当該ポジ型感放射線性樹脂組成物は、[C]感放射線性酸発生剤をさらに含有することが好ましい。当該ポジ型感放射線性樹脂組成物が、[C]感放射線性酸発生剤をさらに含有することで、現像後の露光工程(ポスト露光工程)において、[C]感放射線性酸発生剤から発生する酸によってポリオルガノシオキサン同士の縮合反応が促進される。また、[C]感放射線性酸発生剤は、パターン形成時の放射線とは異なる放射線吸収領域を有していることから、パターン形成時の放射線によっては酸を発生しないか、又は発生してもごく少量であり、ポジ型及びネガ型の感放射線特性が混在して、望ましくない反応が生じることを抑制することができる。 The positive radiation sensitive resin composition preferably further contains [C] a radiation sensitive acid generator. The positive radiation-sensitive resin composition further contains a [C] radiation-sensitive acid generator, so that it is generated from the [C] radiation-sensitive acid generator in an exposure step (post-exposure step) after development. The acid which promotes the condensation reaction between the polyorganothiooxanes. [C] Since the radiation-sensitive acid generator has a radiation absorption region different from the radiation at the time of pattern formation, it does not generate an acid or does not generate an acid depending on the radiation at the time of pattern formation. It is a very small amount, and it is possible to suppress the occurrence of an undesirable reaction due to a mixture of positive and negative radiation sensitive characteristics.
当該ポジ型感放射線性樹脂組成物は、表示素子用層間絶縁膜の形成材料として好適である。 The positive radiation sensitive resin composition is suitable as a material for forming an interlayer insulating film for display elements.
本発明の表示素子用層間絶縁膜の形成方法は、
(1)当該ポジ型感放射線性樹脂組成物の塗膜を基板上に形成する工程、
(2)工程(1)で形成した塗膜の少なくとも一部に放射線を照射する工程、
(3)工程(2)で放射線が照射された塗膜を現像する工程、
(4)工程(3)で現像された塗膜に放射線を照射する工程、及び
(5)工程(4)で放射線が照射された塗膜を加熱する工程
を有する。
The method for forming an interlayer insulating film for a display element according to the present invention includes:
(1) The process of forming the coating film of the said positive type radiation sensitive resin composition on a board | substrate,
(2) A step of irradiating at least a part of the coating film formed in step (1),
(3) A step of developing the coating film irradiated with radiation in step (2),
(4) a step of irradiating the coating film developed in step (3) with radiation; and (5) a step of heating the coating film irradiated with radiation in step (4).
当該ポジ型感放射線性樹脂組成物を用いた本発明の形成方法によると、耐メルトフロー性、耐熱性及び耐溶媒性に優れる表示素子用層間絶縁膜を形成することができる。 According to the forming method of the present invention using the positive radiation sensitive resin composition, an interlayer insulating film for a display element having excellent melt flow resistance, heat resistance and solvent resistance can be formed.
当該ポジ型感放射線性樹脂組成物から形成される表示素子用層間絶縁膜も本発明に好適に含まれる。当該表示素子用層間絶縁膜は、電圧保持率に優れることから表示素子用として好適に適用できる An interlayer insulating film for display elements formed from the positive radiation sensitive resin composition is also suitably included in the present invention. The interlayer insulating film for display elements can be suitably applied for display elements because of its excellent voltage holding ratio.
ここで、「感放射線性樹脂組成物」の「放射線」とは、可視光線、紫外線、遠紫外線、X線、荷電粒子線等を含む概念である。 Here, the “radiation” of the “radiation sensitive resin composition” is a concept including visible light, ultraviolet rays, far ultraviolet rays, X-rays, charged particle beams and the like.
以上説明したように本発明のポジ型感放射線性樹脂組成物は、十分な感度を有し、これを用いた層間絶縁膜の耐メルトフロー性、耐熱性及び耐溶媒性を高め、電圧保持率を向上し、表示素子用として使用することができる。 As described above, the positive radiation sensitive resin composition of the present invention has sufficient sensitivity, and improves the melt flow resistance, heat resistance and solvent resistance of the interlayer insulating film using the composition, and has a voltage holding ratio. And can be used for display elements.
<ポジ型感放射線性樹脂組成物>
本発明のポジ型感放射線性樹脂組成物は、[A]ポリオルガノシロキサンを含有する。また、当該ポジ型感放射線性樹脂組成物は、好適成分として、[B]キノンジアジド化合物及び[C]感放射線性酸発生剤を含有してもよい。さらに、当該ポジ型感放射線性樹脂組成物は、本発明の効果を損なわない範囲で、その他の任意成分を含有してもよい。以下、各成分を詳述する。
<Positive radiation sensitive resin composition>
The positive radiation sensitive resin composition of the present invention contains [A] polyorganosiloxane. Moreover, the said positive type radiation sensitive resin composition may contain a [B] quinonediazide compound and a [C] radiation sensitive acid generator as a suitable component. Furthermore, the positive radiation sensitive resin composition may contain other optional components as long as the effects of the present invention are not impaired. Hereinafter, each component will be described in detail.
<[A]ポリオルガノシロキサン>
[A1]ポリオルガノシロキサンは、ケイ素原子に炭素原子で結合する有機基のうち、エポキシ基を有する有機基の含有割合が、0モル%以上50モル%未満であるポリオルガノシロキサンである。[A2]ポリオルガノシロキサンは、上記含有割合が、50モル%以上100モル%以下であるポリオルガノシロキサンである。当該ポジ型感放射線性樹脂組成物が、[A]ポリオルガノシロキサンを含有し、エポキシ基を有する有機基の含有割合を上記特定範囲とすることで、現像後の加熱工程における耐メルトフロー性、加熱工程後の耐溶媒性及び耐熱性に優れる層間絶縁膜を形成でき、かつ十分な感度を発現することができる。
<[A] polyorganosiloxane>
[A1] The polyorganosiloxane is a polyorganosiloxane in which the content ratio of the organic group having an epoxy group is 0 mol% or more and less than 50 mol% among the organic groups bonded to silicon atoms by carbon atoms. [A2] The polyorganosiloxane is a polyorganosiloxane having the above content ratio of 50 mol% or more and 100 mol% or less. The positive radiation sensitive resin composition contains [A] polyorganosiloxane, and the content ratio of the organic group having an epoxy group is within the above specific range, whereby the melt flow resistance in the heating step after development, An interlayer insulating film having excellent solvent resistance and heat resistance after the heating step can be formed, and sufficient sensitivity can be exhibited.
[A]ポリオルガノシロキサンとしては、下記式(3)で表される構造単位を有するポリオルガノシロキサン、その加水分解物及びその加水分解物の縮合物からなる群より選択される少なくとも1種であることが好ましい。 [A] The polyorganosiloxane is at least one selected from the group consisting of a polyorganosiloxane having a structural unit represented by the following formula (3), a hydrolyzate thereof, and a condensate of the hydrolyzate. It is preferable.
上記式(3)中、R1は、水素原子、炭素数1〜10のアルキル基、炭素数2〜10のアルケニル基、炭素数6〜15のアリール基、又はエポキシ基を有する1価の有機基である。aは、0〜3の整数である。但し、R1が複数の場合、複数のR1は同一であっても複数であってもよい。また、これら基の水素原子の一部又は全部は置換されていてもよい。R2は、水素原子、炭素数1〜6のアルキル基、炭素数1〜6のアシル基、又は炭素数6〜15のアリール基である。但し、R2が複数の場合、複数のR2は同一であっても複数であってもよい。 In the above formula (3), R 1 is a monovalent organic having a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms, or an epoxy group. It is a group. a is an integer of 0-3. However, when R 1 is plural, a plurality of R 1 may be a plurality may be the same. In addition, some or all of the hydrogen atoms of these groups may be substituted. R 2 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 15 carbon atoms. However, when R 2 is plural, R 2 may be a plurality may be the same.
上記R1及びR2が示す炭素数1〜10のアルキル基又は炭素数1〜6のアルキル基としては、例えばメチル基、エチル基、n−プロピル基、n−ブチル基、n−ペンチル基、n−ヘキシル基等が挙げられる。 Examples of the alkyl group having 1 to 10 carbon atoms or the alkyl group having 1 to 6 carbon atoms represented by R 1 and R 2 include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, An n-hexyl group etc. are mentioned.
上記R1が示す炭素数2〜10のアルケニル基としては、例えばエテニル基、プロペニル基等が挙げられる。 Examples of the alkenyl group having 2 to 10 carbon atoms represented by R 1 include an ethenyl group and a propenyl group.
上記R1及びR2が示す炭素数6〜15のアリール基としては、フェニル基等が挙げられる。 Examples of the aryl group having 6 to 15 carbon atoms represented by R 1 and R 2 include a phenyl group.
上記R2が示す炭素数1〜6のアシル基としては、例えばアセチル基等が挙げられる。 Examples of the acyl group having 1 to 6 carbon atoms represented by R 2 include an acetyl group.
上記R1が示すエポキシ基を有する1価の有機基としては、エポキシ基を有する1価の有機基であれば特に限定されず、例えばグリシジル基、グリシジルオキシ基、エポキシシクロヘキシル基を含む基等が挙げられる。エポキシ基を有する1価の有機基としては、上記式(1)及び式(2)で表される基からなる群より選択される少なくとも1種であることが好ましい。上記式(1)中、nは、1〜12の整数である。上記式(2)中、mは、1〜12の整数である。上記式(1)及び式(2)中、*は、ケイ素原子と結合する部位を示す。 The monovalent organic group having an epoxy group represented by R 1 is not particularly limited as long as it is a monovalent organic group having an epoxy group, and examples thereof include a group containing a glycidyl group, a glycidyloxy group, and an epoxycyclohexyl group. Can be mentioned. The monovalent organic group having an epoxy group is preferably at least one selected from the group consisting of groups represented by the above formulas (1) and (2). In said formula (1), n is an integer of 1-12. In said formula (2), m is an integer of 1-12. In the above formulas (1) and (2), * represents a site bonded to a silicon atom.
上記式(1)及び式(2)で表される基としては、下記式(1−1)及び式(1−2)で表される基がより好ましい。[A1]ポリオルガノシロキサン及び[A2]ポリオルガノシロキサン中のエポキシ基を上記特定基とすることで、耐メルトフロー性、耐溶媒性及び耐熱性をより向上させることができる。 As group represented by the said Formula (1) and Formula (2), group represented by following formula (1-1) and Formula (1-2) is more preferable. By making the epoxy group in [A1] polyorganosiloxane and [A2] polyorganosiloxane the above-mentioned specific group, the melt flow resistance, solvent resistance and heat resistance can be further improved.
上記式(1−1)及び式(1−2)中、*は、ケイ素原子と結合する部位を示す。 In the above formula (1-1) and formula (1-2), * represents a site bonded to a silicon atom.
[A2]ポリオルガノシロキサンの含有量は、[A1]ポリオルガノシロキサン100質量部に対して、20質量部以下であることが好ましい。[A2]ポリオルガノシロキサンの含有量を、上記特定量とすることで耐メルトフロー性、耐溶媒性及び耐熱性をより向上させることができる。 [A2] The content of polyorganosiloxane is preferably 20 parts by mass or less with respect to 100 parts by mass of [A1] polyorganosiloxane. [A2] Melt flow resistance, solvent resistance, and heat resistance can be further improved by setting the content of the polyorganosiloxane to the above specific amount.
[A1]ポリオルガノシロキサンのエポキシ基を有する有機基の含有割合としては、0モル%以上10モル%以下が好ましく、0モル%以上5モル%以下がより好ましい。[A2]ポリオルガノシロキサンのエポキシ基を有する有機基の含有割合としては、90モル%以上100モル%以下が好ましく、95モル%以上100モル%以下がより好ましい。[A1]ポリオルガノシロキサン及び[A2]ポリオルガノシロキサン中のエポキシ基を有する有機基の含有割合を上記特定範囲とすることで、耐メルトフロー性、耐溶媒性及び耐熱性を特に向上させることができる。 [A1] The content ratio of the organic group having an epoxy group in the polyorganosiloxane is preferably 0 mol% or more and 10 mol% or less, and more preferably 0 mol% or more and 5 mol% or less. [A2] The content ratio of the organic group having an epoxy group in the polyorganosiloxane is preferably 90 mol% or more and 100 mol% or less, and more preferably 95 mol% or more and 100 mol% or less. By making the content ratio of the organic group having an epoxy group in [A1] polyorganosiloxane and [A2] polyorganosiloxane within the above specified range, the melt flow resistance, solvent resistance and heat resistance can be particularly improved. it can.
[A]ポリオルガノシロキサンの重量平均分子量(Mw)としては、500〜100,000が好ましく、1,000〜10,000がより好ましく、1,000〜5,000が特に好ましい。なお、本明細書における重合体のMw及び数平均分子量(Mn)は下記の条件によるゲルパーミエーションクロマトグラフィー(GPC)により測定した。
装置:GPC−101(昭和電工製)
カラム:GPC−KF−801、GPC−KF−802、GPC−KF−803及びGPC−KF−804を結合
移動相:テトラヒドロフラン
カラム温度:40℃
流速:1.0mL/分
試料濃度:1.0質量%
試料注入量:100μL
検出器:示差屈折計
標準物質:単分散ポリスチレン
[A] The weight average molecular weight (Mw) of the polyorganosiloxane is preferably 500 to 100,000, more preferably 1,000 to 10,000, and particularly preferably 1,000 to 5,000. In addition, Mw and number average molecular weight (Mn) of the polymer in this specification were measured by gel permeation chromatography (GPC) under the following conditions.
Apparatus: GPC-101 (made by Showa Denko)
Column: GPC-KF-801, GPC-KF-802, GPC-KF-803 and GPC-KF-804 combined with mobile phase: tetrahydrofuran Column temperature: 40 ° C.
Flow rate: 1.0 mL / min Sample concentration: 1.0 mass%
Sample injection volume: 100 μL
Detector: Differential refractometer Standard material: Monodisperse polystyrene
<[A]ポリオルガノシロキサンの合成方法>
[A]ポリオルガノシロキサンの合成方法としては、好ましくはエポキシ基を有するシラン化合物、又はエポキシ基を有するシラン化合物と他のシラン化合物との混合物を、好ましくは適当な有機溶媒、水及び触媒の存在下において加水分解又は加水分解縮合することにより合成することができる。
<[A] Synthesis method of polyorganosiloxane>
[A] As a method for synthesizing a polyorganosiloxane, a silane compound having an epoxy group, or a mixture of a silane compound having an epoxy group and another silane compound, preferably the presence of an appropriate organic solvent, water and a catalyst It can synthesize | combine by hydrolyzing or hydrolytic condensation under.
上記エポキシ基を有するシラン化合物としては、例えば3−グリシドキシプロピルトリメトキシシラン、3−グリシドキシプロピルトリエトキシシラン、3−グリシドキシプロピルメチルジメトキシシラン、3−グリシドキシプロピルメチルジエトキシシラン、3−グリシドキシプロピルジメチルメトキシシラン、3−グリシドキシプロピルジメチルエトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン等が挙げられる。 Examples of the silane compound having an epoxy group include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, and 3-glycidoxypropylmethyldiethoxy. Silane, 3-glycidoxypropyldimethylmethoxysilane, 3-glycidoxypropyldimethylethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltriethoxy Silane etc. are mentioned.
上記他のシラン化合物としては、例えばテトラクロロシラン、テトラメトキシシラン、テトラエトキシシラン、テトラ−n−プロポキシシラン、テトラ−i−プロポキシシラン、テトラ−n−ブトキシラン、テトラ−sec−ブトキシシラン、トリクロロシラン、トリメトキシシラン、トリエトキシシラン、トリ−n−プロポキシシラン、トリ−i−プロポキシシラン、トリ−n−ブトキシシラン、トリ−sec−ブトキシシラン、フルオロトリクロロシラン、フルオロトリメトキシシラン、フルオロトリエトキシシラン、フルオロトリ−n−プロポキシシラン、フルオロトリ−i−プロポキシシラン、フルオロトリ−n−ブトキシシラン、フルオロトリ−sec−ブトキシシラン、メチルトリクロロシラン、メチルトリメトキシシラン、メチルトリエトキシシラン、メチルトリ−n−プロポキシシラン、メチルトリ−i−プロポキシシラン、メチルトリ−n−ブトキシシラン、メチルトリ−sec−ブトキシシラン、2−(トリフルオロメチル)エチルトリクロロシラン、2−(トリフルオロメチル)エチルトリメトキシシラン、2−(トリフルオロメチル)、エチルトリエトキシシラン、2−(トリフルオロメチル)エチルトリ−n−プロポキシシラン、2−(トリフルオロメチル)エチルトリ−i−プロポキシシラン、2−(トリフルオロメチル)エチルトリ−n−ブトキシシラン、2−(トリフルオロメチル)エチルトリ−sec−ブトキシシラン、2−(パーフルオロ−n−ヘキシル)エチルトリクロロシラン、2−(パーフルオロ−n−ヘキシル)エチルトリメトキシシラン、2−(パーフルオロ−n−ヘキシル)エチルトリエトキシシラン、2−(パーフルオロ−n−ヘキシル)エチルトリ−n−プロポキシシラン、2−(パーフルオロ−n−ヘキシル)エチルトリ−i−プロポキシシラン、2−(パーフルオロ−n−ヘキシル)エチルトリ−n−ブトキシシラン、2−(パーフルオロ−n−ヘキシル)エチルトリ−sec−ブトキシシラン、2−(パーフルオロ−n−オクチル)エチルトリクロロシラン、2−(パーフルオロ−n−オクチル)エチルトリメトキシシラン、2−(パーフルオロ−n−オクチル)エチルトリエトキシシラン、2−(パーフルオロ−n−オクチル)エチルトリ−n−プロポキシシラン、2−(パーフルオロ−n−オクチル)エチルトリ−i−プロポキシシラン、2−(パーフルオロ−n−オクチル)エチルトリ−n−ブトキシシラン、2−(パーフルオロ−n−オクチル)エチルトリ−sec−ブトキシシラン、ヒドロキシメチルトリクロロシラン、ヒドロキシメチルトリメトキシシラン、ヒドロキシエチルトリメトキシシラン、ヒドロキシメチルトリ−n−プロポキシシラン、ヒドロキシメチルトリ−i−プロポキシシラン、ヒドロキシメチルトリ−n−ブトキシシラン、ヒドロキシメチルトリ−sec−ブトキシシラン、3−(メタ)アクリロキシプロピルトリクロロシラン、3−(メタ)アクリロキシプロピルトリメトキシシラン、3−(メタ)アクリロキシプロピルトリエトキシシラン、3−(メタ)アクリロキシプロピルトリ−n−プロポキシシラン、3−(メタ)アクリロキシプロピルトリ−i−プロポキシシラン、3−(メタ)アクリロキシプロピルトリ−n−ブトキシシラン、3−(メタ)アクリロキシプロピルトリ−sec−ブトキシシラン、3−メルカプトプロピルトリクロロシラン、3−メルカプトプロピルトリメトキシシラン、3−メルカプトプロピルトリエトキシシラン、3−メルカプトプロピルトリ−n−プロポキシシラン、3−メルカプトプロピルトリ−i−プロポキシシラン、3−メルカプトプロピルトリ−n−ブトキシシラン、3−メルカプトプロピルトリ−sec−ブトキシシラン、メルカプトメチルトリメトキシシラン、メルカプトメチルトリエトキシシラン、ビニルトリクロロシラン、ビニルトリメトキシシラン、ビニルトリエトキシシラン、ビニルトリ−n−プロポキシシラン、ビニルトリ−i−プロポキシシラン、ビニルトリ−n−ブトキシシラン、ビニルトリ−sec−ブトキシシラン、アリルトリクロロシラン、アリルトリメトキシシラン、アリルトリエトキシシラン、アリルトリ−n−プロポキシシラン、アリルトリ−i−プロポキシシラン、アリルトリ−n−ブトキシシラン、アリルトリ−sec−ブトキシシラン、フェニルトリクロロシラン、フェニルトリメトキシシラン、フェニルトリエトキシシラン、フェニルトリ−n−プロポキシシラン、フェニルトリ−i−プロポキシシラン、フェニルトリ−n−ブトキシシラン、フェニルトリ−sec−ブトキシシラン、メチルジクロロシラン、メチルジメトキシシラン、メチルジエトキシシラン、メチルジ−n−プロポキシシラン、メチルジ−i−プロポキシシラン、メチルジ−n−ブトキシシラン、メチルジ−sec−ブトキシシラン、ジメチルジクロロシラン、ジメチルジメトキシシラン、ジメチルジエトキシシラン、ジメチルジ−n−プロポキシシラン、ジメチルジ−i−プロポキシシラン、ジメチルジ−n−ブトキシシラン、ジメチルジ−sec−ブトキシシラン、(メチル)〔2−(パーフルオロ−n−オクチル)エチル〕ジクロロシラン、(メチル)〔2−(パーフルオロ−n−オクチル)エチル〕ジメトキシシラン、(メチル)〔2−(パーフルオロ−n−オクチル)エチル〕ジエメトキシシラン、(メチル)〔2−(パーフルオロ−n−オクチル)エチル〕ジ−n−プロポキシシラン、(メチル)〔2−(パーフルオロ−n−オクチル)エチル〕ジ−i−プロポキシシラン、(メチル)〔2−(パーフルオロ−n−オクチル)エチル〕ジ−n−ブトキシシラン、(メチル)〔2−(パーフルオロ−n−オクチル)エチル〕ジ−sec−ブトキシシラン、(メチル)(3−メルカプトプロピル)ジクロロシラン、(メチル)(3−メルカプトプロピル)ジメトキシシラン、(メチル)(3−メルカプトプロピル)ジエトキシシラン、(メチル)(3−メルカプトプロピル)ジ−n−プロポキシシラン、(メチル)(3−メルカプトプロピル)ジ−i−プロポキシシラン、(メチル)(3−メルカプトプロピル)ジ−n−ブトキシシラン、(メチル)(3−メルカプトプロピル)ジ−sec−ブトキシシラン、(メチル)(ビニル)ジクロロシラン、(メチル)(ビニル)ジメトキシシラン、(メチル)(ビニル)ジエトキシシラン、(メチル)(ビニル)ジ−n−プロポキシシラン、(メチル)(ビニル)ジ−i−プロポキシシラン、(メチル)(ビニル)ジ−n−ブトキシシラン、(メチル)(ビニル)ジ−sec−ブトキシシラン、ジビニルジクロロシラン、ジビニルジメトキシシラン、ジビニルジエトキシシラン、ジビニルジ−n−プロポキシシラン、ジビニルジ−i−プロポキシシラン、ジビニルジ−n−ブトキシシラン、ジビニルジ−sec−ブトキシシラン、ジフェニルジクロロシラン、ジフェニルジメトキシシラン、ジフェニルジエトキシシラン、ジフェニルジ−n−プロポキシシラン、ジフェニルジ−i−プロポキシシラン、ジフェニルジ−n−ブトキシシラン、ジフェニルジ−sec−ブトキシシラン、クロロジメチルシラン、メトキシジメチルシラン、エトキシジメチルシラン、クロロトリメチルシラン、ブロモトリメチルシラン、ヨードトリメチルシラン、メトキシトリメチルシラン、エトキシトリメチルシラン、n−プロポキシトリメチルシラン、i−プロポキシトリメチルシラン、n−ブトキシトリメチルシラン、sec−ブトキシトリメチルシラン、t−ブトキシトリメチルシラン、(クロロ)(ビニル)ジメチルシラン、(メトキシ)(ビニル)ジメチルシラン、(エトキシ)(ビニル)ジメチルシラン、(クロロ)(メチル)ジフェニルシラン、(メトキシ)(メチル)ジフェニルシラン、(エトキシ)(メチル)ジフェニルシラン等が挙げられる。 Examples of the other silane compounds include tetrachlorosilane, tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-i-propoxysilane, tetra-n-butoxysilane, tetra-sec-butoxysilane, trichlorosilane, Trimethoxysilane, triethoxysilane, tri-n-propoxysilane, tri-i-propoxysilane, tri-n-butoxysilane, tri-sec-butoxysilane, fluorotrichlorosilane, fluorotrimethoxysilane, fluorotriethoxysilane, Fluorotri-n-propoxysilane, fluorotri-i-propoxysilane, fluorotri-n-butoxysilane, fluorotri-sec-butoxysilane, methyltrichlorosilane, methyltrimethoxysilane, Rutriethoxysilane, methyltri-n-propoxysilane, methyltri-i-propoxysilane, methyltri-n-butoxysilane, methyltri-sec-butoxysilane, 2- (trifluoromethyl) ethyltrichlorosilane, 2- (trifluoromethyl) Ethyltrimethoxysilane, 2- (trifluoromethyl), ethyltriethoxysilane, 2- (trifluoromethyl) ethyltri-n-propoxysilane, 2- (trifluoromethyl) ethyltri-i-propoxysilane, 2- (tri Fluoromethyl) ethyltri-n-butoxysilane, 2- (trifluoromethyl) ethyltri-sec-butoxysilane, 2- (perfluoro-n-hexyl) ethyltrichlorosilane, 2- (perfluoro-n-hexyl) ethyltri Methoxy Lan, 2- (perfluoro-n-hexyl) ethyltriethoxysilane, 2- (perfluoro-n-hexyl) ethyltri-n-propoxysilane, 2- (perfluoro-n-hexyl) ethyltri-i-propoxysilane 2- (perfluoro-n-hexyl) ethyltri-n-butoxysilane, 2- (perfluoro-n-hexyl) ethyltri-sec-butoxysilane, 2- (perfluoro-n-octyl) ethyltrichlorosilane, 2 -(Perfluoro-n-octyl) ethyltrimethoxysilane, 2- (perfluoro-n-octyl) ethyltriethoxysilane, 2- (perfluoro-n-octyl) ethyltri-n-propoxysilane, 2- (perfluorosilane Fluoro-n-octyl) ethyltri-i-propoxysilane, 2- (Perful Olo-n-octyl) ethyltri-n-butoxysilane, 2- (perfluoro-n-octyl) ethyltri-sec-butoxysilane, hydroxymethyltrichlorosilane, hydroxymethyltrimethoxysilane, hydroxyethyltrimethoxysilane, hydroxymethyltri -N-propoxysilane, hydroxymethyltri-i-propoxysilane, hydroxymethyltri-n-butoxysilane, hydroxymethyltri-sec-butoxysilane, 3- (meth) acryloxypropyltrichlorosilane, 3- (meth) acryl Loxypropyltrimethoxysilane, 3- (meth) acryloxypropyltriethoxysilane, 3- (meth) acryloxypropyltri-n-propoxysilane, 3- (meth) acryloxypropyltri-i-propo Sisilane, 3- (meth) acryloxypropyltri-n-butoxysilane, 3- (meth) acryloxypropyltri-sec-butoxysilane, 3-mercaptopropyltrichlorosilane, 3-mercaptopropyltrimethoxysilane, 3-mercapto Propyltriethoxysilane, 3-mercaptopropyltri-n-propoxysilane, 3-mercaptopropyltri-i-propoxysilane, 3-mercaptopropyltri-n-butoxysilane, 3-mercaptopropyltri-sec-butoxysilane, mercapto Methyltrimethoxysilane, mercaptomethyltriethoxysilane, vinyltrichlorosilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltri-n-propoxysilane, vinyltri-i-propoxy Vinyltri-n-butoxysilane, vinyltri-sec-butoxysilane, allyltrichlorosilane, allyltrimethoxysilane, allyltriethoxysilane, allyltri-n-propoxysilane, allyltri-i-propoxysilane, allyltri-n-butoxysilane Allyltri-sec-butoxysilane, phenyltrichlorosilane, phenyltrimethoxysilane, phenyltriethoxysilane, phenyltri-n-propoxysilane, phenyltri-i-propoxysilane, phenyltri-n-butoxysilane, phenyltri-sec -Butoxysilane, methyldichlorosilane, methyldimethoxysilane, methyldiethoxysilane, methyldi-n-propoxysilane, methyldi-i-propoxysilane, methyldi-n-butoxy Silane, methyldi-sec-butoxysilane, dimethyldichlorosilane, dimethyldimethoxysilane, dimethyldiethoxysilane, dimethyldi-n-propoxysilane, dimethyldi-i-propoxysilane, dimethyldi-n-butoxysilane, dimethyldi-sec-butoxysilane, (Methyl) [2- (perfluoro-n-octyl) ethyl] dichlorosilane, (methyl) [2- (perfluoro-n-octyl) ethyl] dimethoxysilane, (methyl) [2- (perfluoro-n- Octyl) ethyl] dimethoxysilane, (methyl) [2- (perfluoro-n-octyl) ethyl] di-n-propoxysilane, (methyl) [2- (perfluoro-n-octyl) ethyl] di-i -Propoxysilane, (methyl) [2- (perfluoro-n- (Cutyl) ethyl] di-n-butoxysilane, (methyl) [2- (perfluoro-n-octyl) ethyl] di-sec-butoxysilane, (methyl) (3-mercaptopropyl) dichlorosilane, (methyl) ( 3-mercaptopropyl) dimethoxysilane, (methyl) (3-mercaptopropyl) diethoxysilane, (methyl) (3-mercaptopropyl) di-n-propoxysilane, (methyl) (3-mercaptopropyl) di-i- Propoxysilane, (methyl) (3-mercaptopropyl) di-n-butoxysilane, (methyl) (3-mercaptopropyl) di-sec-butoxysilane, (methyl) (vinyl) dichlorosilane, (methyl) (vinyl) Dimethoxysilane, (methyl) (vinyl) diethoxysilane, (methyl) (vinyl) di n-propoxysilane, (methyl) (vinyl) di-i-propoxysilane, (methyl) (vinyl) di-n-butoxysilane, (methyl) (vinyl) di-sec-butoxysilane, divinyldichlorosilane, divinyldimethoxy Silane, divinyldiethoxysilane, divinyldi-n-propoxysilane, divinyldi-i-propoxysilane, divinyldi-n-butoxysilane, divinyldi-sec-butoxysilane, diphenyldichlorosilane, diphenyldimethoxysilane, diphenyldiethoxysilane, diphenyldi -N-propoxysilane, diphenyldi-i-propoxysilane, diphenyldi-n-butoxysilane, diphenyldi-sec-butoxysilane, chlorodimethylsilane, methoxydimethylsilane, ethoxydimethylsilane Chlorotrimethylsilane, bromotrimethylsilane, iodotrimethylsilane, methoxytrimethylsilane, ethoxytrimethylsilane, n-propoxytrimethylsilane, i-propoxytrimethylsilane, n-butoxytrimethylsilane, sec-butoxytrimethylsilane, t-butoxytrimethylsilane , (Chloro) (vinyl) dimethylsilane, (methoxy) (vinyl) dimethylsilane, (ethoxy) (vinyl) dimethylsilane, (chloro) (methyl) diphenylsilane, (methoxy) (methyl) diphenylsilane, (ethoxy) ( And methyl) diphenylsilane.
上記他のシラン化合物の市販品としては、例えばKC−89、KC−89S、X−21−3153、X−21−5841、X−21−5842、X−21−5843、X−21−5844、X−21−5845、X−21−5846、X−21−5847、X−21−5848、X−22−160AS、X−22−170B、X−22−170BX、X−22−170D、X−22−170DX、X−22−176B、X−22−176D、X−22−176DX、X−22−176F、X−40−2308、X−40−2651、X−40−2655A、X−40−2671、X−40−2672、X−40−9220、X−40−9225、X−40−9227、X−40−9246、X−40−9247、X−40−9250、X−40−9323、X−41−1053、X−41−1056、X−41−1805、X−41−1810、KF6001、KF6002、KF6003、KR212、KR−213、KR−217、KR220L、KR242A、KR271、KR282、KR300、KR311、KR401N、KR500、KR510、KR5206、KR5230、KR5235、KR9218、KR9706(以上、信越化学工業製);グラスレジン(昭和電工製);SH804、SH805、SH806A、SH840、SR2400、SR2402、SR2405、SR2406、SR2410、SR2411、SR2416、SR2420(以上、東レ・ダウコーニング製);FZ3711、FZ3722(以上、日本ユニカー製);DMS−S12、DMS−S15、DMS−S21、DMS−S27、DMS−S31、DMS−S32、DMS−S33、DMS−S35、DMS−S38、DMS−S42、DMS−S45、DMS−S51、DMS−227、PSD−0332、PDS−1615、PDS−9931、XMS−5025(以上、チッソ製);メチルシリケートMS51、メチルシリケートMS56(以上、三菱化学製);エチルシリケート28、エチルシリケート40、エチルシリケート48(以上、コルコート製);GR100、GR650、GR908、GR950(以上、昭和電工製)等が挙げられる。 Examples of commercially available products of the other silane compounds include KC-89, KC-89S, X-21-3153, X-21-5841, X-21-5842, X-21-5844, X-21-5844, X-21-5845, X-21-5847, X-21-5847, X-21-5848, X-22-160AS, X-22-170B, X-22-170BX, X-22-170D, X- 22-170DX, X-22-176B, X-22-176D, X-22-176DX, X-22-176F, X-40-2308, X-40-2651, X-40-2655A, X-40- 2671, X-40-2672, X-40-9220, X-40-9225, X-40-9227, X-40-9246, X-40-9247, X-40-9250, X-4 -9323, X-41-1053, X-41-1056, X-41-1805, X-41-1810, KF6001, KF6002, KF6003, KR212, KR-213, KR-217, KR220L, KR242A, KR271, KR282 , KR300, KR311, KR401N, KR500, KR510, KR5206, KR5230, KR5235, KR9218, KR9706 (manufactured by Shin-Etsu Chemical Co., Ltd.); glass resin (manufactured by Showa Denko); SH804, SH805, SH806A, SH840, SR2240, SR2402 SR2406, SR2410, SR2411, SR2416, SR2420 (above, manufactured by Toray Dow Corning); FZ3711, FZ3722 (above, manufactured by Nihon Unicar); DMS- 12, DMS-S15, DMS-S21, DMS-S27, DMS-S31, DMS-S32, DMS-S33, DMS-S35, DMS-S38, DMS-S42, DMS-S45, DMS-S51, DMS-227, PSD-0332, PDS-1615, PDS-9931, XMS-5025 (above, manufactured by Chisso); Methyl silicate MS51, Methyl silicate MS56 (above, manufactured by Mitsubishi Chemical); Ethyl silicate 28, ethyl silicate 40, ethyl silicate 48 (above , Manufactured by Colcoat); GR100, GR650, GR908, GR950 (above, manufactured by Showa Denko) and the like.
これらの他のシラン化合物のうち、得られる層間絶縁膜の耐溶媒性の観点から、テトラメトキシシラン、テトラエトキシシラン、メチルトリメトキシシラン、エチルトリメトキシシラン、メチルトリエトキシシラン、テトラエトキシシラン、3−(メタ)アクリロキシプロピルトリメトキシシラン、3−(メタ)アクリロキシプロピルトリエトキシシラン、ビニルトリメトキシシラン、ビニルトリエトキシシラン、アリルトリメトキシシラン、アリルトリエトキシシラン、フェニルトリメトキシシラン、フェニルトリエトキシシラン、3−メルカプトプロピルトリメトキシシラン、3−メルカプトプロピルトリエトキシシラン、メルカプトメチルトリメトキシシラン、メルカプトメチルトリエトキシシラン、ジメチルジメトキシシラン、ジメチルジエトキシシランが好ましい。 Among these other silane compounds, from the viewpoint of solvent resistance of the obtained interlayer insulating film, tetramethoxysilane, tetraethoxysilane, methyltrimethoxysilane, ethyltrimethoxysilane, methyltriethoxysilane, tetraethoxysilane, 3 -(Meth) acryloxypropyltrimethoxysilane, 3- (meth) acryloxypropyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, allyltrimethoxysilane, allyltriethoxysilane, phenyltrimethoxysilane, phenyltri Ethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-mercaptopropyltriethoxysilane, mercaptomethyltrimethoxysilane, mercaptomethyltriethoxysilane, dimethyldimethoxysilane, dimethyl Distearate triethoxysilane are preferred.
[A]ポリオルガノシロキサンのエポキシ当量としては、100g/モル〜10,000g/モルが好ましく、150g/モル〜1,000g/モルがより好ましい。従って、[A]ポリオルガノシロキサンの合成に際しては、エポキシ基を有するシラン化合物と他のシラン化合物との使用割合を、上記の好適なエポキシ当量の範囲となるように調製することが好ましい。具体的には、エポキシ基を有するシラン化合物の含有量としては、他のシラン化合物との合計に対して0質量%〜50質量%が好ましく、5質量%〜30質量%がより好ましい。 [A] The epoxy equivalent of the polyorganosiloxane is preferably 100 g / mol to 10,000 g / mol, and more preferably 150 g / mol to 1,000 g / mol. Therefore, when synthesizing [A] polyorganosiloxane, it is preferable to prepare the use ratio of the silane compound having an epoxy group and the other silane compound within the range of the above-mentioned preferable epoxy equivalent. Specifically, as content of the silane compound which has an epoxy group, 0 mass%-50 mass% are preferable with respect to the sum total with another silane compound, and 5 mass%-30 mass% are more preferable.
[A]ポリオルガノシロキサンの合成に際し、使用できる有機溶媒としては、例えば炭化水素系溶媒、ケトン系溶媒、エステル系溶媒、エーテル系溶媒、アルコール系溶媒等が挙げられる。 [A] Examples of organic solvents that can be used in the synthesis of polyorganosiloxane include hydrocarbon solvents, ketone solvents, ester solvents, ether solvents, alcohol solvents, and the like.
上記炭化水素系溶媒としては、例えばトルエン、キシレン等が挙げられる。上記ケトン系溶媒としては、例えばメチルエチルケトン、メチルイソブチルケトン、メチルn−アミルケトン、ジエチルケトン、シクロヘキサノン等が挙げられる。上記エステル系溶媒としては、例えば酢酸エチル、酢酸n−ブチル、酢酸i−アミル、プロピレングリコールモノメチルエーテルアセテート、3−メトキシブチルアセテート、乳酸エチル等が挙げられる。上記エーテル系溶媒としては、例えばエチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、テトラヒドロフラン、ジオキサン等が挙げられる。上記アルコール系溶媒としては、例えば1−ヘキサノール、4−メチル−2−ペンタノール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノ−n−プロピルエーテル、エチレングリコールモノ−n−ブチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノ−n−プロピルエーテル等が挙げられる。これらのうち非水溶性のものが好ましい。これらの有機溶媒は、単独又は2種以上を混合して使用することができる。 Examples of the hydrocarbon solvent include toluene and xylene. Examples of the ketone solvent include methyl ethyl ketone, methyl isobutyl ketone, methyl n-amyl ketone, diethyl ketone, and cyclohexanone. Examples of the ester solvent include ethyl acetate, n-butyl acetate, i-amyl acetate, propylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, and ethyl lactate. Examples of the ether solvent include ethylene glycol dimethyl ether, ethylene glycol diethyl ether, tetrahydrofuran, dioxane and the like. Examples of the alcohol solvent include 1-hexanol, 4-methyl-2-pentanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, propylene Examples include glycol monomethyl ether, propylene glycol monoethyl ether, and propylene glycol mono-n-propyl ether. Of these, water-insoluble ones are preferred. These organic solvents can be used individually or in mixture of 2 or more types.
有機溶媒の含有量としては、全シラン化合物100質量部に対して、好ましくは10質量部〜10,000質量部、より好ましくは50質量部〜1,000質量部である。また、[A]ポリオルガノシロキサンを製造する際の水の含有量としては、全シラン化合物に対して、好ましくは0.5倍モル〜100倍モル、より好ましくは1倍モル〜30倍モルである。 The content of the organic solvent is preferably 10 parts by mass to 10,000 parts by mass, and more preferably 50 parts by mass to 1,000 parts by mass with respect to 100 parts by mass of the total silane compounds. Moreover, as content of water at the time of manufacturing [A] polyorganosiloxane, Preferably it is 0.5 times mole-100 times mole with respect to all the silane compounds, More preferably, it is 1 times mole-30 times mole. is there.
上記触媒としては例えばアルカリ金属化合物、有機塩基、チタン化合物、ジルコニウム化合物等が挙げられる。 Examples of the catalyst include alkali metal compounds, organic bases, titanium compounds, zirconium compounds and the like.
上記アルカリ金属化合物としては、例えば水酸化ナトリウム、水酸化カリウム、ナトリウムメトキシド、カリウムメトキシド、ナトリウムエトキシド、カリウムエトキシド等が挙げられる。 Examples of the alkali metal compound include sodium hydroxide, potassium hydroxide, sodium methoxide, potassium methoxide, sodium ethoxide, potassium ethoxide and the like.
上記有機塩基としては、例えばエチルアミン、ジエチルアミン、ピペラジン、ピペリジン、ピロリジン、ピロール等の1〜2級有機アミン;トリエチルアミン、トリ−n−プロピルアミン、トリ−n−ブチルアミン、ピリジン、4−ジメチルアミノピリジン、ジアザビシクロウンデセン等の3級有機アミン;テトラメチルアンモニウムヒドロキシド等の4級有機アンモニウム塩等が挙げられる。 Examples of the organic base include primary and secondary organic amines such as ethylamine, diethylamine, piperazine, piperidine, pyrrolidine and pyrrole; triethylamine, tri-n-propylamine, tri-n-butylamine, pyridine, 4-dimethylaminopyridine, And tertiary organic amines such as diazabicycloundecene; quaternary organic ammonium salts such as tetramethylammonium hydroxide.
上記触媒としては、アルカリ金属化合物、有機塩基が好ましい。アルカリ金属化合物又は有機塩基を触媒として用いることにより、エポキシ基の開環等の副反応を生じることなく、高い加水分解・縮合速度でポリオルガノシロキサンを得ることができ、生産安定性に優れる。理由としては、Chemical Reviews、95巻、p1409(1995年)に指摘されているように、加水分解、縮合反応において触媒としてアルカリ金属化合物又は有機塩基を用いると、ランダム構造、はしご型構造又はかご型構造が形成され、シラノール基の含有割合が少ないポリオルガノシロキサンが得られるためではないかと推察される。これらの有機塩基のうち、有機塩基がより好ましく、反応が穏やかに進行する観点から、トリエチルアミン、トリ−n−プロピルアミン、トリ−n−ブチルアミン、ピリジン、4−ジメチルアミノピリジン、テトラメチルアンモニウムヒドロキシドが特に好ましい。 As said catalyst, an alkali metal compound and an organic base are preferable. By using an alkali metal compound or an organic base as a catalyst, a polyorganosiloxane can be obtained at a high hydrolysis / condensation rate without causing side reactions such as ring opening of an epoxy group, and the production stability is excellent. The reason is that, as pointed out in Chemical Reviews, Vol. 95, p1409 (1995), when an alkali metal compound or an organic base is used as a catalyst in a hydrolysis or condensation reaction, a random structure, a ladder structure or a cage structure is used. It is presumed that a structure is formed and a polyorganosiloxane having a low content of silanol groups is obtained. Among these organic bases, organic bases are more preferable, and triethylamine, tri-n-propylamine, tri-n-butylamine, pyridine, 4-dimethylaminopyridine, tetramethylammonium hydroxide are preferred from the viewpoint that the reaction proceeds gently. Is particularly preferred.
上記触媒の含有量としては、種類、温度等により異なるが、全シラン化合物に対して好ましくは0.01倍モル〜3倍モルであり、より好ましくは0.05倍モル〜1倍モルである。 The content of the catalyst varies depending on the type, temperature, and the like, but is preferably 0.01-fold to 3-fold mole, more preferably 0.05-fold mole to 1-fold mole with respect to all silane compounds. .
[A]ポリオルガノシロキサンを合成する際の加水分解又は加水分解縮合反応は、エポキシ基を有するシラン化合物と必要に応じて他のシラン化合物とを有機溶媒に溶解し、この溶液を有機塩基及び水と混合して、例えば油浴等により加熱することにより実施することが好ましい。 [A] Hydrolysis or hydrolysis-condensation reaction when synthesizing polyorganosiloxane involves dissolving an epoxy group-containing silane compound and, if necessary, another silane compound in an organic solvent, and dissolving this solution with an organic base and water. It is preferable to carry out by mixing with, for example, heating in an oil bath or the like.
加水分解縮合反応における油浴の加熱温度としては、好ましくは130℃以下、より好ましくは40℃〜100℃である。加熱時間としては、好ましくは0.5時間〜12時間、より好ましくは1時間〜8時間である。加熱中は、混合液を撹拌してもよいし、還流下に置いてもよい。 The heating temperature of the oil bath in the hydrolysis condensation reaction is preferably 130 ° C. or lower, more preferably 40 ° C. to 100 ° C. The heating time is preferably 0.5 hours to 12 hours, more preferably 1 hour to 8 hours. During heating, the mixture may be stirred or placed under reflux.
反応終了後、反応液から分取した有機溶媒層を水で洗浄することが好ましい。この洗浄に際しては、洗浄操作が容易になる観点から、少量の塩を含む水、例えば0.2質量%程度の硝酸アンモニウム水溶液等で洗浄することが好ましい。洗浄は洗浄後の水層が中性になるまで行い、その後有機溶媒層を、必要に応じて無水硫酸カルシウム、モレキュラーシーブス等の乾燥剤で乾燥した後、溶媒を除去することで目的とする[A]ポリオルガノシロキサンが得られる。 After completion of the reaction, the organic solvent layer separated from the reaction solution is preferably washed with water. In this cleaning, from the viewpoint of facilitating the cleaning operation, it is preferable to perform cleaning with water containing a small amount of salt, for example, an aqueous ammonium nitrate solution of about 0.2% by mass. The washing is performed until the washed aqueous layer becomes neutral, and then the organic solvent layer is dried with a desiccant such as anhydrous calcium sulfate or molecular sieves if necessary, and then the target is removed by removing the solvent [ A] A polyorganosiloxane is obtained.
[A]ポリオルガノシロキサンとしては、市販品を用いてもよい。市販品としては、例えばDMS−E01、DMS−E12、DMS−E21,EMS−32(以上、チッソ製)等が挙げられる。 [A] A commercially available product may be used as the polyorganosiloxane. As a commercial item, DMS-E01, DMS-E12, DMS-E21, EMS-32 (above, the product made by Chisso) etc. are mentioned, for example.
[A]ポリオルガノシロキサンは、エポキシ基を有するポリオルガノシロキサン自体が加水分解されて生じる加水分解物に由来する部分や、エポキシ基を有するポリオルガノシロキサン同士が加水分解縮合した加水分解縮合物に由来する部分を含んでいてもよい。 [A] Polyorganosiloxane is derived from a hydrolyzed product formed by hydrolysis of an epoxy group-containing polyorganosiloxane itself, or from a hydrolyzed condensate obtained by hydrolytic condensation of polyorganosiloxanes having an epoxy group. It may contain a part to do.
<[B]キノンジアジド化合物>
当該ポジ型感放射線性樹脂組成物が好適成分として含有できる[B]キノンジアジド化合物は、放射線の照射によってカルボン酸を発生する。当該ポジ型感放射線性樹脂組成物が[B]キノンジアジド化合物をさらに含有することで、露光された部分が現像工程により除去されるポジ型の感放射線特性を当該ポジ型感放射線性樹脂組成物に付与することができる。
<[B] quinonediazide compound>
The [B] quinonediazide compound that can be contained as a suitable component in the positive radiation sensitive resin composition generates a carboxylic acid upon irradiation with radiation. When the positive radiation sensitive resin composition further contains a [B] quinonediazide compound, the positive radiation sensitive characteristic in which the exposed portion is removed by the development process is added to the positive radiation sensitive resin composition. Can be granted.
[B]キノンジアジド化合物としては、好ましくはフェノール性水酸基を有する化合物とナフトキノンジアジドスルホン酸ハライドとの縮合物が挙げられる。 [B] The quinonediazide compound is preferably a condensate of a compound having a phenolic hydroxyl group and naphthoquinonediazidesulfonic acid halide.
フェノール性水酸基を有する化合物としては、例えばフェノール性水酸基のオルト位及びパラ位が、それぞれ独立して水素原子又は下記式で表される置換基である化合物が挙げられる。 Examples of the compound having a phenolic hydroxyl group include compounds in which the ortho position and the para position of the phenolic hydroxyl group are each independently a hydrogen atom or a substituent represented by the following formula.
上記式中、R3、R4及びR5は、それぞれ独立して置換されていてもよい炭素数1〜10のアルキル基、カルボキシル基又は置換されていてもよいフェニル基である。また、R3及びR4が結合して、互いに結合している炭素原子と共に環構造を形成してもよい。 In said formula, R < 3 >, R < 4 > and R < 5 > are the C1-C10 alkyl groups which may be substituted each independently, a carboxyl group, or the phenyl group which may be substituted. R 3 and R 4 may be bonded together to form a ring structure together with the carbon atoms bonded to each other.
上記R3、R4及びR5が示す炭素数1〜10のアルキル基としては、例えばメチル基、エチル基、n−プロピル基、i−プロピル基、n−ブチル基、i−ブチル基、t−ブチル基、n−ヘキシル基、シクロヘキシル基、n−ヘプチル基、n−オクチル基、トリフルオロメチル基、2−カルボキシエチル基が挙げられる。 Examples of the alkyl group having 1 to 10 carbon atoms represented by R 3 , R 4 and R 5 include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, t -Butyl group, n-hexyl group, cyclohexyl group, n-heptyl group, n-octyl group, trifluoromethyl group, 2-carboxyethyl group may be mentioned.
上記R3、R4及びR5が示す置換されていてもよいフェニル基の置換基としては、例えば水酸基等が挙げられる。 Examples of the substituent of the optionally substituted phenyl group represented by R 3 , R 4 and R 5 include a hydroxyl group.
上記R3及びR4が結合して、互いに結合している炭素原子と共に形成してもよい環構造としては、例えばシクロペンタン、シクロヘキサン、アダマンタン、フルオレン等が挙げられる。 Examples of the ring structure formed by combining R 3 and R 4 together with the carbon atoms bonded to each other include cyclopentane, cyclohexane, adamantane, and fluorene.
フェノール性水酸基を有する化合物としては、例えば下記式で表される化合物等が挙げられる。 Examples of the compound having a phenolic hydroxyl group include compounds represented by the following formulas.
これらのうち、フェノール性水酸基を有する化合物としては、4,4’−[1−[4−[1−(4−ヒドロキシフェニル)−1−メチルエチル]フェニル]エチリデン]ビスフェノール、1,1,1−トリ(p−ヒドロキシフェニル)エタンが好ましい。 Among these, as the compound having a phenolic hydroxyl group, 4,4 ′-[1- [4- [1- (4-hydroxyphenyl) -1-methylethyl] phenyl] ethylidene] bisphenol, 1,1,1 -Tri (p-hydroxyphenyl) ethane is preferred.
上記ナフトキノンジアジドスルホン酸ハライドとしては、例えば1,2−ナフトキノンジアジド−4−スルホン酸クロリド、1,2−ナフトキノンジアジド−5−スルホン酸クロリドが挙げられる。1,2−ナフトキノンジアジド−4−スルホン酸クロリドから得られるエステル化合物(キノンジアジド化合物)は、i線(波長365nm)領域に吸収を持つため、i線露光に適している。一方、1,2−ナフトキノンジアジド−5−スルホン酸クロリドから得られるエステル化合物(キノンジアジド化合物)は、広範囲の波長領域に吸収が存在するため、広範囲の波長での露光に適している。 Examples of the naphthoquinone diazide sulfonic acid halide include 1,2-naphthoquinone diazide-4-sulfonic acid chloride and 1,2-naphthoquinone diazide-5-sulfonic acid chloride. An ester compound (quinonediazide compound) obtained from 1,2-naphthoquinonediazide-4-sulfonic acid chloride is suitable for i-line exposure since it has absorption in the i-line (wavelength 365 nm) region. On the other hand, an ester compound (quinonediazide compound) obtained from 1,2-naphthoquinonediazide-5-sulfonic acid chloride is suitable for exposure in a wide range of wavelengths since absorption exists in a wide range of wavelengths.
[B]キノンジアジド化合物としては、4,4’−[1−[4−[1−(4−ヒドロキシフェニル)−1−メチルエチル]フェニル]エチリデン]ビスフェノールと1,2−ナフトキノンジアジド−5−スルホン酸クロリドとの縮合物、1,1,1−トリ(p−ヒドロキシフェニル)エタンと1,2−ナフトキノンジアジド−5−スルホン酸クロリドとの縮合物が好ましい。 [B] The quinonediazide compound includes 4,4 ′-[1- [4- [1- (4-hydroxyphenyl) -1-methylethyl] phenyl] ethylidene] bisphenol and 1,2-naphthoquinonediazide-5-sulfone. A condensate of acid chloride, a condensate of 1,1,1-tri (p-hydroxyphenyl) ethane and 1,2-naphthoquinonediazide-5-sulfonic acid chloride is preferred.
[B]キノンジアジド化合物のMwとしては、好ましくは300〜1,500、より好ましくは350〜1,200である。[B]キノンジアジド化合物のMwを300以上とすることで、形成される層間絶縁膜の透明性を高く維持することができる。一方、[B]キノンジアジド化合物のMwを1,500以下とすることで、当該ポジ型感放射線性樹脂組成物のパターン形成性の低下を抑制することができる。 [B] The Mw of the quinonediazide compound is preferably 300 to 1,500, more preferably 350 to 1,200. [B] By setting Mw of the quinonediazide compound to 300 or more, the transparency of the formed interlayer insulating film can be maintained high. On the other hand, when the Mw of the [B] quinonediazide compound is 1,500 or less, it is possible to suppress a decrease in pattern formation of the positive radiation sensitive resin composition.
[B]キノンジアジド化合物は、単独又は2種以上を組み合わせて用いることができる。当該ポジ型感放射線性樹脂組成物における[B]キノンジアジド化合物の含有量としては、[A]ポリオルガノシロキサン100質量部に対して、好ましくは1質量部〜100質量部であり、より好ましくは5質量部〜50質量部である。[B]キノンジアジド化合物の含有量を上記特定範囲とすることで、現像液となるアルカリ水溶液に対する放射線の照射部分と未照射部分との溶解度の差が大きくなり、結果としてパターニング性能が良好となる。また、得られる層間絶縁膜の耐溶媒性も良好となる。 [B] The quinonediazide compounds can be used alone or in combination of two or more. The content of [B] quinonediazide compound in the positive radiation sensitive resin composition is preferably 1 part by mass to 100 parts by mass, more preferably 5 parts per 100 parts by mass of [A] polyorganosiloxane. Part by mass to 50 parts by mass. [B] By making content of a quinonediazide compound into the said specific range, the difference of the solubility of the irradiated part with respect to the alkaline aqueous solution used as a developing solution and the unirradiated part becomes large, and patterning performance becomes favorable as a result. Moreover, the solvent resistance of the obtained interlayer insulating film is also improved.
<[C]感放射線性酸発生剤>
当該ポジ型感放射線性樹脂組成物が好適成分として含有できる[C]感放射線性酸発生剤は、[B]キノンジアジド化合物の極大吸収波長より短い極大吸収波長を有しており、その吸収波長の放射線の照射によって酸、好ましくはパーフルオロスルホン酸等の強酸を発生する化合物である。当該ポジ型感放射線性樹脂組成物が、[C]感放射線性酸発生剤をさらに含有することで、ポスト露光工程において、[C]感放射線性酸発生剤から発生する酸によってポリオルガノシオキサン同士の縮合反応が促進される。また、[C]感放射線性酸発生剤は、パターン形成時の放射線とは異なる放射線吸収領域を有していることから、パターン形成時の放射線によっては酸を発生しないか、又は発生してもごく少量であり、ポジ型及びネガ型の感放射線特性が混在して、望ましくない反応が生じることを抑制することができる。
<[C] Radiation sensitive acid generator>
The [C] radiation sensitive acid generator that can be contained as a suitable component in the positive radiation sensitive resin composition has a maximum absorption wavelength shorter than the maximum absorption wavelength of the [B] quinonediazide compound. It is a compound that generates an acid, preferably a strong acid such as perfluorosulfonic acid, upon irradiation with radiation. The positive-type radiation-sensitive resin composition further contains a [C] radiation-sensitive acid generator, so that in the post-exposure step, the polyorganothiooxane is generated by an acid generated from the [C] radiation-sensitive acid generator. The condensation reaction between them is promoted. [C] Since the radiation-sensitive acid generator has a radiation absorption region different from the radiation at the time of pattern formation, it does not generate an acid or does not generate an acid depending on the radiation at the time of pattern formation. It is a very small amount, and it is possible to suppress the occurrence of an undesirable reaction due to a mixture of positive and negative radiation sensitive characteristics.
[C]感放射線性酸発生剤としては、[B]キノンジアジド化合物の極大吸収波長より短い極大吸収波長を有し、かつその吸収波長の放射線の照射によって酸を発生する化合物であれば特に限定されない。[B]キノンジアジド化合物の極大吸収波長と[C]感放射線性酸発生剤の極大吸収波長との波長差は、パターン形成時の露光又はポスト露光における放射線照射により、実質的にいずれか一方の放射線吸収を選択的に発生させるような値であればよい。上記波長差としては、10nm〜200nmが好ましく、20nm〜100nmがより好ましい。 [C] The radiation-sensitive acid generator is not particularly limited as long as it is a compound having a maximum absorption wavelength shorter than the maximum absorption wavelength of the [B] quinonediazide compound and generating an acid upon irradiation with radiation having the absorption wavelength. . [B] The wavelength difference between the maximum absorption wavelength of the quinonediazide compound and the maximum absorption wavelength of the [C] radiation-sensitive acid generator is substantially equal to any one of the radiations upon exposure to radiation during pattern formation or post-exposure. Any value that selectively generates absorption may be used. The wavelength difference is preferably 10 nm to 200 nm, and more preferably 20 nm to 100 nm.
[C]感放射線性酸発生剤としては、下記式(4)〜(6)で表される化合物が好ましい。 [C] As the radiation-sensitive acid generator, compounds represented by the following formulas (4) to (6) are preferable.
上記式(4)中、R6及びR7は、それぞれ独立して水素原子、水酸基、炭素数1〜12の直鎖状若しくは分岐状アルキル基、又は炭素数1〜12のアルコキシ基である。Xaは、SbF6、(CbH2b+1)YPF6−Y、又はCbF2b+1SO3である。Yは、0〜6の整数である。bは、1〜6の整数である。
上記式(5)中、R8は、フェニル基、ナフチル基、アントラニル基又はフェニルチオ基である。Xbは、上記式(4)におけるXaと同義である。
上記式(6)中、R9及びR10は、それぞれ独立して、炭素数1〜12のアルキル基、炭素数4〜20の脂環式アルキル基、又は置換されていてもよいアリール基である。
In the formula (4), R 6 and R 7 are each independently a hydrogen atom, a hydroxyl group, a linear or branched alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. Xa is, SbF 6, a (C b H 2b + 1) Y PF 6-Y or C b F 2b + 1 SO 3 ,. Y is an integer of 0-6. b is an integer of 1-6.
In the above formula (5), R 8 is a phenyl group, a naphthyl group, anthranyl group or phenylthio group. X b has the same meaning as X a in the above formula (4).
In the above formula (6), R 9 and R 10 are each independently an alkyl group having 1 to 12 carbon atoms, an alicyclic alkyl group having 4 to 20 carbon atoms, or an optionally substituted aryl group. is there.
上記式(4)で表される化合物としては、例えば1−(4−ヒドロキシ−1−ナフタレニル)テトラヒドロチオフェニウムトリフルオロメタンスルホナート、1−(4−n−ブトキシ−1−ナフタレニル)テトラヒドロチオフェニウムトリフルオロメタンスルホナート、1−(4,7−ジエトキシ−1−ナフタレニル)テトラヒドロチオフェニウムトリフルオロメタンスルホナート、1−(4,7−ジブトキシ−1−ナフタレニル)テトラヒドロチオフェニウムトリフルオロメタンスルホナート、1−(4,7−ジヒドロキシ−1−ナフタレニル)テトラヒドロチオフェニウムトリフルオロメタンスルホナート、1−(4,7−ジプロピルヒドロキシ−1−ナフタレニル)テトラヒドロチオフェニウムトリフルオロメタンスルホナート、1−(4,7−ジヒドロキシ−1−ナフタレニル)テトラヒドロチオフェニウムヘキサフルオロホスフェート、1−(4,7−ジヒドロキシ−1−ナフタレニル)テトラヒドロチオフェニウムヘキサフルオロホスフェート等が挙げられる。これらのうち、1−(4,7−ジブトキシ−1−ナフタレニル)テトラヒドロチオフェニウムトリフルオロメタンスルホナート、1−(4,7−ジヒドロキシ−1−ナフタレニル)テトラヒドロチオフェニウムトリフルオロメタンスルホナートが好ましい。 Examples of the compound represented by the above formula (4) include 1- (4-hydroxy-1-naphthalenyl) tetrahydrothiophenium trifluoromethanesulfonate, 1- (4-n-butoxy-1-naphthalenyl) tetrahydrothiophene. Nium trifluoromethanesulfonate, 1- (4,7-diethoxy-1-naphthalenyl) tetrahydrothiophenium trifluoromethanesulfonate, 1- (4,7-dibutoxy-1-naphthalenyl) tetrahydrothiophenium trifluoromethanesulfonate, 1- (4,7-dihydroxy-1-naphthalenyl) tetrahydrothiophenium trifluoromethanesulfonate, 1- (4,7-dipropylhydroxy-1-naphthalenyl) tetrahydrothiophenium trifluoromethanesulfonate, 4,7-dihydroxy-1-naphthalenyl) tetrahydrothiophenium hexafluorophosphate, 1- (4,7-dihydroxy-1-naphthalenyl) tetrahydrothiophenium hexafluorophosphate, and the like. Of these, 1- (4,7-dibutoxy-1-naphthalenyl) tetrahydrothiophenium trifluoromethanesulfonate and 1- (4,7-dihydroxy-1-naphthalenyl) tetrahydrothiophenium trifluoromethanesulfonate are preferred.
上記式(5)で表される化合物としては、例えばジフェニル(4−(フェニルチオ)フェニル)スルホニウムトリフルオロメタンスルホナート、ジフェニル(4−(フェニルチオ)フェニル)スルホニウムヘキサフルオロホスフェート、ジフェニル(4−(フェニルチオ)フェニル)スルホニウムヘキサフルオロアンチモネート、ジフェニル(4−(フェニルチオ)フェニル)スルホニウムトリフルオロトリスペンタフルオロエチルホスファート、ジフェニル(4−(フェニル)フェニル)スルホニウムトリフルオロトリスペンタフルオロエチルホスファート、ジフェニル(4−(ナフチル)フェニル)スルホニウムトリフルオロトリスペンタフルオロエチルホスファート、ジフェニル(4−(アントラニル)フェニル)スルホニウムトリフルオロトリスペンタフルオロエチルホスファート等が挙げられる。これらのうち、ジフェニル(4−(フェニルチオ)フェニル)スルホニウムトリフルオロトリスペンタフルオロエチルホスファート、ジフェニル(4−(フェニル)フェニル)スルホニウムトリフルオロトリスペンタフルオロエチルホスファートが好ましい。 Examples of the compound represented by the above formula (5) include diphenyl (4- (phenylthio) phenyl) sulfonium trifluoromethanesulfonate, diphenyl (4- (phenylthio) phenyl) sulfonium hexafluorophosphate, and diphenyl (4- (phenylthio)). Phenyl) sulfonium hexafluoroantimonate, diphenyl (4- (phenylthio) phenyl) sulfonium trifluorotrispentafluoroethyl phosphate, diphenyl (4- (phenyl) phenyl) sulfonium trifluorotrispentafluoroethyl phosphate, diphenyl (4- (Naphthyl) phenyl) sulfonium trifluorotrispentafluoroethyl phosphate, diphenyl (4- (anthranyl) phenyl) sulfonium trif Oro tris pentafluoroethyl phosphate and the like. Of these, diphenyl (4- (phenylthio) phenyl) sulfonium trifluorotrispentafluoroethyl phosphate and diphenyl (4- (phenyl) phenyl) sulfonium trifluorotrispentafluoroethyl phosphate are preferred.
上記式(6)で表される化合物としては、例えばビス(t−ブチルスルホニル)ジアゾメタン、ビス(シクロヘキシルスルホニル)ジアゾメタン、ビス(ベンゼンスルホニル)ジアゾメタン、ビス(p−トルエンスルホニル)ジアゾメタン、ビス(4−t−ブチルベンゼンスルホニル)ジアゾメタン、ビス(ナフタレンスルホニル)ジアゾメタン、ビス(アントラセンスルホニル)ジアゾメタン等が挙げられる。これらのうち、ビス(シクロヘキシルスルホニル)ジアゾメタン、ビス(p−トルエンスルホニル)ジアゾメタンが好ましい。 Examples of the compound represented by the above formula (6) include bis (t-butylsulfonyl) diazomethane, bis (cyclohexylsulfonyl) diazomethane, bis (benzenesulfonyl) diazomethane, bis (p-toluenesulfonyl) diazomethane, bis (4- and t-butylbenzenesulfonyl) diazomethane, bis (naphthalenesulfonyl) diazomethane, and bis (anthracenesulfonyl) diazomethane. Of these, bis (cyclohexylsulfonyl) diazomethane and bis (p-toluenesulfonyl) diazomethane are preferred.
[C]感放射線性酸発生剤は、単独又は2種以上を組み合わせて用いることができる。当該ポジ型感放射線性樹脂組成物における[C]感放射線性酸発生剤の含有量としては、ポスト露光時に、[A]ポリオルガノシロキサンの縮合反応を促進し、架橋構造を強固にし得る限り特に限定されないが、[A]ポリオルガノシロキサン100質量部に対して、0.5質量部〜5質量部が好ましく、1質量部〜4質量部がより好ましい。[C]感放射線性酸発生剤の含有量を上記特定範囲とすることで、加熱工程における熱に対しても高い耐メルトフロー性を発揮することができる。 [C] The radiation-sensitive acid generator can be used alone or in combination of two or more. The content of the [C] radiation sensitive acid generator in the positive radiation sensitive resin composition is particularly as long as it can promote the condensation reaction of [A] polyorganosiloxane and strengthen the crosslinked structure during post exposure. Although not limited, 0.5 mass part-5 mass parts are preferable with respect to 100 mass parts of [A] polyorganosiloxane, and 1 mass part-4 mass parts are more preferable. [C] By making content of a radiation sensitive acid generator into the said specific range, the high melt flow resistance with respect to the heat | fever in a heating process can be exhibited.
<その他の任意成分>
当該ポジ型感放射線性樹脂組成物は、上記の[A]ポリオルガノシロキサン、[B]キノンジアジド化合物及び[C]感放射線性酸発生剤に加え、本発明の効果を損なわない範囲で必要に応じて熱架橋性化合物、界面活性剤、脱水剤等のその他の任意成分を含有できる。これらのその他の任意成分は、それぞれの成分を単独で使用してもよいし2種以上を混合して使用してもよい。以下、順に詳述する。
<Other optional components>
In addition to the above [A] polyorganosiloxane, [B] quinonediazide compound and [C] radiation sensitive acid generator, the positive type radiation sensitive resin composition may be used as long as the effects of the present invention are not impaired. And other optional components such as a heat-crosslinkable compound, a surfactant, and a dehydrating agent. These other optional components may be used alone or in combination of two or more. Hereinafter, it explains in full detail in order.
[熱架橋性化合物]
熱架橋性化合物は、加熱工程における熱硬化時に[A]ポリオルガノシロキサンを架橋する化合物であり、当該ポジ型感放射線性樹脂組成物が熱架橋性化合物を含むことで層間絶縁膜の架橋度が高くなり、結果として耐溶媒性及び耐メルトフロー性が向上する。
[Thermal crosslinkable compound]
The heat crosslinkable compound is a compound that crosslinks [A] polyorganosiloxane during heat curing in the heating step, and the degree of crosslinkage of the interlayer insulating film is increased by including the heat-crosslinkable compound in the positive radiation sensitive resin composition. As a result, the solvent resistance and the melt flow resistance are improved.
熱架橋性化合物としては、例えば上述の「他のシラン化合物」等の[A]ポリオルガノシロキサンと構造が重複しないシラン化合物であって、複数のアルコキシ基又はハロゲン原子を有するシラン化合物が挙げられる。 Examples of the thermally crosslinkable compound include silane compounds having a structure that does not overlap with the polyorganosiloxane [A] such as the above-mentioned “other silane compound” and having a plurality of alkoxy groups or halogen atoms.
熱架橋性化合物の含有量としては、[A]ポリオルガノシロキサン100質量部に対して、好ましくは1質量部以上70質量部以下、より好ましくは5質量部以上50質量部以下である。熱架橋性化合物の含有量を上記特定範囲とすることで、放射線感度、耐メルトフロー性及び耐溶媒性をより向上することができる。 The content of the thermally crosslinkable compound is preferably 1 part by mass or more and 70 parts by mass or less, and more preferably 5 parts by mass or more and 50 parts by mass or less with respect to 100 parts by mass of [A] polyorganosiloxane. Radiation sensitivity, melt flow resistance, and solvent resistance can be further improved by setting the content of the thermally crosslinkable compound within the above specific range.
[界面活性剤]
界面活性剤は、当該ポジ型感放射線性樹脂組成物の塗布性の改善、塗布ムラの低減、放射線照射部の現像性を改良するために添加することができる。界面活性剤としては、例えばフッ素系界面活性剤、シリコーン系界面活性剤及びその他の界面活性剤が挙げられる。
[Surfactant]
The surfactant can be added to improve the coating property of the positive radiation-sensitive resin composition, reduce coating unevenness, and improve the developability of the radiation irradiated part. Examples of the surfactant include a fluorine-based surfactant, a silicone-based surfactant, and other surfactants.
上記フッ素系界面活性剤としては、末端、主鎖及び側鎖の少なくともいずれかの部位にフルオロアルキル基及び/又はフルオロアルキレン基を有する化合物が好ましく、例えば1,1,2,2−テトラフロロ−n−オクチル(1,1,2,2−テトラフロロ−n−プロピル)エーテル、1,1,2,2−テトラフロロ−n−オクチル(n−ヘキシル)エーテル、ヘキサエチレングリコールジ(1,1,2,2,3,3−ヘキサフロロ−n−ペンチル)エーテル、オクタエチレングリコールジ(1,1,2,2−テトラフロロ−n−ブチル)エーテル、ヘキサプロピレングリコールジ(1,1,2,2,3,3−ヘキサフロロ−n−ペンチル)エーテル、オクタプロピレングリコールジ(1,1,2,2−テトラフロロ−n−ブチル)エーテル、パーフロロ−n−ドデカンスルホン酸ナトリウム、1,1,2,2,3,3−ヘキサフロロ−n−デカン、1,1,2,2,8,8,9,9,10,10−デカフロロ−n−ドデカンや、フロロアルキルベンゼンスルホン酸ナトリウム、フロロアルキルリン酸ナトリウム、フロロアルキルカルボン酸ナトリウム、ジグリセリンテトラキス(フロロアルキルポリオキシエチレンエーテル)、フロロアルキルアンモニウムヨージド、フロロアルキルベタイン、他のフロロアルキルポリオキシエチレンエーテル、パーフロロアルキルポリオキシエタノール、パーフロロアルキルアルコキシレート、カルボン酸フロロアルキルエステル等が挙げられる。 The fluorine-based surfactant is preferably a compound having a fluoroalkyl group and / or a fluoroalkylene group in at least one of the terminal, main chain and side chain, for example, 1,1,2,2-tetrafluoro-n. -Octyl (1,1,2,2-tetrafluoro-n-propyl) ether, 1,1,2,2-tetrafluoro-n-octyl (n-hexyl) ether, hexaethylene glycol di (1,1,2, 2,3,3-hexafluoro-n-pentyl) ether, octaethylene glycol di (1,1,2,2-tetrafluoro-n-butyl) ether, hexapropylene glycol di (1,1,2,2,3, 3-hexafluoro-n-pentyl) ether, octapropylene glycol di (1,1,2,2-tetrafluoro-n-butyl) ether Sodium perfluoro-n-dodecanesulfonate, 1,1,2,2,3,3-hexafluoro-n-decane, 1,1,2,2,8,8,9,9,10,10-decafluoro-n -Dodecane, sodium fluoroalkylbenzenesulfonate, sodium fluoroalkylphosphate, sodium fluoroalkylcarboxylate, diglycerin tetrakis (fluoroalkylpolyoxyethylene ether), fluoroalkylammonium iodide, fluoroalkylbetaine, other fluoroalkylpolyoxy Examples thereof include ethylene ether, perfluoroalkyl polyoxyethanol, perfluoroalkyl alkoxylate, and carboxylic acid fluoroalkyl ester.
フッ素系界面活性剤の市販品としては、例えばBM−1000、BM−1100(以上、BM CHEMIE製)、メガファックF142D、同F172、同F173、同F183、同F178、同F191、同F471、同F476(以上、大日本インキ化学工業製)、フロラードFC−170C、同−171、同−430、同−431(以上、住友スリーエム製)、サーフロンS−112、同−113、同−131、同−141、同−145、同−382、サーフロンSC−101、同−102、同−103、同−104、同−105、同−106(以上、旭硝子製)、エフトップEF301、同303、同352(以上、新秋田化成製)、フタージェントFT−100、同−110、同−140A、同−150、同−250、同−251、同−300、同−310、同−400S、FTX−218、同−251(以上、ネオス製)等が挙げられる。 Examples of commercially available fluorosurfactants include BM-1000, BM-1100 (above, manufactured by BM CHEMIE), MegaFuck F142D, F172, F173, F183, F178, F191, F191, and F471. F476 (above, manufactured by Dainippon Ink and Chemicals), Florard FC-170C, -171, -430, -431 (above, manufactured by Sumitomo 3M), Surflon S-112, -113, -131, -141, -145, -382, Surflon SC-101, -102, -103, -104, -105, -106 (above made by Asahi Glass), F-top EF301, 303, 352 (manufactured by Shin-Akita Kasei), FT FT-100, -110, -140A, -150, -250, and -25 , The -300, the -310, the -400S, FTX-218, the -251 (or, Neos Co., Ltd.) and the like.
シリコーン系界面活性剤の市販品としては、例えばトーレシリコーンDC3PA、同DC7PA、同SH11PA、同SH21PA、同SH28PA、同SH29PA、同SH30PA、同SH−190、同SH−193、同SH−8400、同SZ−6032、同SF−8428、同DC−57、同DC−190(以上、東レ・ダウコーニング・シリコーン製)、TSF−4440、TSF−4300、TSF−4445、TSF−4446、TSF−4460、TSF−4452(以上、GE東芝シリコーン製)、オルガノシロキサンポリマーKP341(信越化学工業製)等が挙げられる。 Examples of commercially available silicone surfactants include Torresilicone DC3PA, DC7PA, SH11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH-190, SH-193, SH-8400, and SH-8400. SZ-6032, SF-8428, DC-57, DC-190 (made by Toray Dow Corning Silicone), TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460, Examples thereof include TSF-4442 (manufactured by GE Toshiba Silicone), organosiloxane polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), and the like.
その他の界面活性剤としては、例えばポリオキシエチレンラウリルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンオレイルエーテル等のポリオキシエチレンアルキルエーテル;ポリオキシエチレン−n−オクチルフェニルエーテル、ポリオキシエチレン−n−ノニルフェニルエーテル等のポリオキシエチレンアリールエーテル;ポリオキシエチレンジラウレート、ポリオキシエチレンジステアレート等のポリオキシエチレンジアルキルエステル等のノニオン系界面活性剤、(メタ)アクリル酸系共重合体ポリフローNo.57、同No.95(以上、共栄社化学製)等が挙げられる。 Examples of other surfactants include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, and polyoxyethylene oleyl ether; polyoxyethylene-n-octylphenyl ether, polyoxyethylene-n- Polyoxyethylene aryl ethers such as nonylphenyl ether; nonionic surfactants such as polyoxyethylene dialkyl esters such as polyoxyethylene dilaurate and polyoxyethylene distearate; (meth) acrylic acid copolymer polyflow No. 57, no. 95 (manufactured by Kyoeisha Chemical Co., Ltd.).
界面活性剤の含有量としては、[A]ポリオルガノシロキサン100質量部に対して、0.01質量部以上10質量部以下が好ましく、0.05質量部以上5質量部以下がより好ましい。界面活性剤の含有量を上記特定範囲とすることで当該ポジ型感放射線性樹脂組成物の塗布性を最適化することができる。 As content of surfactant, 0.01 mass part or more and 10 mass parts or less are preferable with respect to 100 mass parts of [A] polyorganosiloxane, and 0.05 mass part or more and 5 mass parts or less are more preferable. By setting the content of the surfactant within the above specific range, the applicability of the positive radiation sensitive resin composition can be optimized.
[脱水剤]
脱水剤は、水を化学反応により水以外の物質に変換するか、又は水を物理吸着若しくは包接によりトラップすることができる物質として定義される。当該ポジ型感放射線性樹脂組成物に、脱水剤を含有させることで、環境から浸入する水分、又は当該ポジ型感放射線性樹脂組成物の現像後の加熱工程における縮合反応の結果、発生する水分を低減することができる。結果として、当該ポジ型感放射線性樹脂組成物の保存安定性を向上させることができる。さらに、縮合反応性を高め、当該ポジ型感放射線性樹脂組成物の耐メルトフロー性を向上させることができると考えられる。
[Dehydrating agent]
A dehydrating agent is defined as a substance that can convert water into a substance other than water by a chemical reaction or trap water by physical adsorption or inclusion. By containing a dehydrating agent in the positive-type radiation-sensitive resin composition, moisture that enters from the environment, or moisture generated as a result of the condensation reaction in the heating step after development of the positive-type radiation-sensitive resin composition Can be reduced. As a result, the storage stability of the positive radiation sensitive resin composition can be improved. Furthermore, it is considered that the condensation reactivity can be increased and the melt flow resistance of the positive radiation sensitive resin composition can be improved.
脱水剤としては、例えばカルボン酸エステル、アセタール類(ケタール類を含む)、カルボン酸無水物等が挙げられる。 Examples of the dehydrating agent include carboxylic acid esters, acetals (including ketals), carboxylic acid anhydrides, and the like.
カルボン酸エステルとしては、オルトカルボン酸エステル、カルボン酸シリルエステルが好ましい。オルトカルボン酸エステルとしては、例えばオルト蟻酸メチル、オルト蟻酸エチル、オルト蟻酸プロピル、オルト蟻酸ブチル、オルト酢酸メチル、オルト酢酸エチル、オルト酢酸プロピル、オルト酢酸ブチル、オルトプロピオン酸メチル、オルトプロピオン酸エチルが挙げられる。カルボン酸シリルエステルとしては、例えば酢酸トリメチルシリル、酢酸トリブチルシリル、蟻酸トリメチルシリル、シュウ酸トリメチルシリル等が挙げられる。これらのうち、オルトカルボン酸エステルがより好ましく、オルト蟻酸メチル等のオルト蟻酸エステルが特に好ましい。 As the carboxylic acid ester, orthocarboxylic acid ester and carboxylic acid silyl ester are preferable. Examples of orthocarboxylic acid esters include methyl orthoformate, ethyl orthoformate, propyl orthoformate, butyl orthoformate, methyl orthoacetate, ethyl orthoacetate, propyl orthoacetate, butyl orthoacetate, methyl orthopropionate, and ethyl orthopropionate. Can be mentioned. Examples of the carboxylic acid silyl ester include trimethylsilyl acetate, tributylsilyl acetate, trimethylsilyl formate, and trimethylsilyl oxalate. Of these, orthocarboxylic acid esters are more preferable, and orthoformate such as methyl orthoformate is particularly preferable.
アセタール類としては、例えばケトン類とアルコールとの反応物、ケトン類とジアルコールとの反応物、ケテンシリルアセタール類等が挙げられる。これらのうち、ケトン類とアルコールとの反応物が好ましく、ケトン類とアルコールとの反応物としては、例えばジメチルアセタール、ジエチルアセタール、ジプロピルアセタール等が挙げられる。 Examples of acetals include a reaction product of ketones and alcohol, a reaction product of ketones and dialcohol, and ketene silyl acetals. Of these, a reaction product of a ketone and an alcohol is preferable, and examples of the reaction product of a ketone and an alcohol include dimethyl acetal, diethyl acetal, and dipropyl acetal.
カルボン酸無水物としては、例えば無水蟻酸、無水酢酸、無水コハク酸、無水マレイン酸、無水フタル酸、無水安息香酸、酢酸安息香酸無水物等が挙げられる。これらのうち、無水酢酸、無水コハク酸が好ましい。 Examples of the carboxylic acid anhydride include formic anhydride, acetic anhydride, succinic anhydride, maleic anhydride, phthalic anhydride, benzoic anhydride, and acetic acid benzoic anhydride. Of these, acetic anhydride and succinic anhydride are preferred.
脱水剤の含有量としては、[A]ポリオルガノシロキサン100質量部に対して、好ましくは0.001質量部以上50質量部以下であり、より好ましくは0.01質量部以上30質量部以下であり、特に好ましくは0.05質量部以上10質量部以下である。脱水剤の含有量を上記特定範囲とすることで、当該ポジ型感放射線性樹脂組成物の保存安定性を最適化することができる。 The content of the dehydrating agent is preferably 0.001 to 50 parts by mass, more preferably 0.01 to 30 parts by mass, with respect to 100 parts by mass of [A] polyorganosiloxane. Yes, particularly preferably 0.05 parts by mass or more and 10 parts by mass or less. By setting the content of the dehydrating agent in the specific range, the storage stability of the positive radiation-sensitive resin composition can be optimized.
<ポジ型感放射線性樹脂組成物の調製方法>
当該ポジ型感放射線性樹脂組成物は、例えば[A]ポリオルガノシロキサンに加え、好適成分である[B]キノンジアジド化合物、[C]感放射線性酸発生剤、並びにその他の任意成分を所定の割合で混合することによって調製される。当該ポジ型感放射線性樹脂組成物は、好ましくは適当な溶媒に溶解又は分散させた状態に調製され、使用される。
<Method for preparing positive-type radiation-sensitive resin composition>
The positive-type radiation-sensitive resin composition includes, for example, [A] polyorganosiloxane, [B] quinonediazide compound, [C] radiation-sensitive acid generator, and other optional components as predetermined components in a predetermined ratio. Prepared by mixing with. The positive type radiation sensitive resin composition is preferably prepared and used in a state of being dissolved or dispersed in a suitable solvent.
当該ポジ型感放射線性樹脂組成物の調製に用いられる溶媒としては、各成分を均一に溶解又は分散し、各成分と反応しないものが好適に用いられる。このような溶媒としては、例えば、上述した[A]ポリオルガノシロキサンを合成するために使用できる溶媒として例示したものと同様のものが挙げられる。溶媒は、単独で又は2種以上を混合して使用できる。 As the solvent used for the preparation of the positive radiation sensitive resin composition, a solvent in which each component is uniformly dissolved or dispersed and does not react with each component is preferably used. As such a solvent, the thing similar to what was illustrated as a solvent which can be used in order to synthesize | combine the [A] polyorganosiloxane mentioned above, for example is mentioned. A solvent can be used individually or in mixture of 2 or more types.
各成分の溶解性、各成分との反応性、塗膜形成の容易性等の観点から、酢酸ジエチレングリコールモノエチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールエチルメチルエーテル、ジエチレングリコールジメチルエーテル、プロピレングリコールモノメチルエーテル、酢酸エチレングリコールモノブチルエーテル、酢酸プロピレングリコールモノメチルエーテル、酢酸ジプロピレングリコールモノメチルエーテル、酢酸3−メトキシブチル、酢酸シクロヘキサノール、ベンジルアルコール、3−メトキシブタノールが好ましい。 From the viewpoints of solubility of each component, reactivity with each component, ease of film formation, etc., diethylene glycol monoethyl ether, diethylene glycol diethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol dimethyl ether, propylene glycol monomethyl ether, ethylene glycol acetate Monobutyl ether, propylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, cyclohexanol acetate, benzyl alcohol, and 3-methoxybutanol are preferred.
さらに、上記溶媒とともに膜厚の面内均一性を高めるため、高沸点溶媒を併用できる。高沸点溶媒としては、例えばN−メチルピロリドン、N,N−ジメチルアセトアミド、ベンジルエチルエーテル、ジヘキシルエーテル、アセトニルアセトン、1−オクタノール、1−ノナノール、酢酸ベンジル、安息香酸エチル、シュウ酸ジエチル、マレイン酸ジエチル、γ−ブチロラクトン、炭酸プロピレン等が挙げられる。これらのうち、N−メチルピロリドン、γ−ブチロラクトン、N,N−ジメチルアセトアミドが好ましい。 Furthermore, in order to improve the in-plane uniformity of the film thickness together with the above solvent, a high boiling point solvent can be used in combination. Examples of the high boiling point solvent include N-methylpyrrolidone, N, N-dimethylacetamide, benzyl ethyl ether, dihexyl ether, acetonyl acetone, 1-octanol, 1-nonanol, benzyl acetate, ethyl benzoate, diethyl oxalate, malein Examples include diethyl acid, γ-butyrolactone, and propylene carbonate. Of these, N-methylpyrrolidone, γ-butyrolactone, and N, N-dimethylacetamide are preferable.
当該ポジ型感放射線性樹脂組成物を溶液状態として調製する場合、固形分濃度(組成物溶液中に占める溶媒以外の成分)は、使用目的や所望の膜厚の値等に応じて任意の濃度(例えば5質量%〜50質量%)に設定できる。より好ましい固形分濃度としては、基板上への塗膜の形成方法により異なるが、好ましくは5質量%〜50質量%、より好ましくは10質量%〜40質量%、特に好ましくは15質量%〜35質量%である。 When the positive radiation-sensitive resin composition is prepared in a solution state, the solid content concentration (components other than the solvent in the composition solution) can be any concentration depending on the purpose of use, the desired film thickness, etc. (For example, 5 mass%-50 mass%) can be set. The more preferable solid content concentration varies depending on the method of forming a coating film on the substrate, but is preferably 5% by mass to 50% by mass, more preferably 10% by mass to 40% by mass, and particularly preferably 15% by mass to 35%. % By mass.
<表示素子用層間絶縁膜の形成方法>
当該ポジ型感放射線性樹脂組成物は表示素子用層間絶縁膜の形成材料として好適である。当該ポジ型感放射線性樹脂組成を用いた本発明の表示素子用層間絶縁膜の形成方法は、
(1)当該ポジ型感放射線性樹脂組成物の塗膜を基板上に形成する工程、
(2)工程(1)で形成した塗膜の少なくとも一部に放射線を照射する工程、
(3)工程(2)で放射線が照射された塗膜を現像する工程、
(4)工程(3)で現像された塗膜に放射線を照射する工程、及び
(5)工程(4)で放射線が照射された塗膜を加熱する工程
を有する。
<Method for forming interlayer insulating film for display element>
The positive radiation sensitive resin composition is suitable as a material for forming an interlayer insulating film for display elements. The method for forming an interlayer insulating film for a display element of the present invention using the positive radiation sensitive resin composition,
(1) The process of forming the coating film of the said positive type radiation sensitive resin composition on a board | substrate,
(2) A step of irradiating at least a part of the coating film formed in step (1),
(3) A step of developing the coating film irradiated with radiation in step (2),
(4) a step of irradiating the coating film developed in step (3) with radiation; and (5) a step of heating the coating film irradiated with radiation in step (4).
当該ポジ型感放射線性樹脂組成物を用いた本発明の形成方法によると、耐メルトフロー性、耐熱性及び耐溶媒性に優れる表示素子用層間絶縁膜を形成することができる。また、当該ポジ型感放射線性樹脂組成物から形成される表示素子用層間絶縁膜も本発明に好適に含まれる。当該表示素子用層間絶縁膜は、電圧保持率に優れることから表示素子用として好適に適用できる。以下、各工程を詳述する。 According to the forming method of the present invention using the positive radiation sensitive resin composition, an interlayer insulating film for a display element having excellent melt flow resistance, heat resistance and solvent resistance can be formed. Moreover, the interlayer insulation film for display elements formed from the said positive radiation sensitive resin composition is also suitably contained in this invention. Since the interlayer insulating film for display elements is excellent in voltage holding ratio, it can be suitably applied for display elements. Hereinafter, each process is explained in full detail.
[工程(1)]
本工程では、当該ポジ型感放射線性樹脂組成物の塗膜を基板上に形成する。形成方法としては、例えば基板上に当該ポジ型感放射線性樹脂組成物の溶液又は分散液を塗布した後、好ましくは塗布面を加熱(プレベーク)することにより溶媒を除去して、塗膜を形成する。
[Step (1)]
In this step, a coating film of the positive radiation sensitive resin composition is formed on the substrate. As a forming method, for example, after applying the solution or dispersion of the positive radiation sensitive resin composition on a substrate, the solvent is removed by preferably heating (pre-baking) the coating surface to form a coating film. To do.
基板としては、例えば石英;シリコン;ソーダライムガラス、無アルカリガラス等のガラス基板;ポリエチレンテレフタレート、ポリブチレンテレフタレート、ポリエーテルスルホン、ポリカーボネート、ポリイミド等の樹脂基板等が挙げられる。 Examples of the substrate include quartz; silicon; glass substrates such as soda lime glass and non-alkali glass; and resin substrates such as polyethylene terephthalate, polybutylene terephthalate, polyethersulfone, polycarbonate, and polyimide.
当該ポジ型感放射線性樹脂組成物の塗布方法としては、例えばスプレー法、ロールコート法、スピンコート法、スリット塗布法、バー塗布法、インクジェット塗布法等が挙げられる。これらのうち、スピンコート法、スリット塗布法が好ましい。 Examples of the coating method of the positive radiation sensitive resin composition include a spray method, a roll coating method, a spin coating method, a slit coating method, a bar coating method, and an ink jet coating method. Of these, spin coating and slit coating are preferred.
上記プレベークの条件としては、各成分の種類、配合割合等によって異なるが、70℃〜120℃が好ましく、1分〜10分間程度である。塗膜のプレベーク後の膜厚は、0.5μm〜10μmが好ましく、1.0μm〜7.0μm程度がより好ましい。 The prebaking conditions vary depending on the type of each component, the blending ratio, and the like, but are preferably 70 ° C. to 120 ° C. and about 1 minute to 10 minutes. The film thickness after pre-baking of the coating film is preferably 0.5 μm to 10 μm, and more preferably about 1.0 μm to 7.0 μm.
[工程(2)]
本工程では、工程(1)で形成した塗膜の少なくとも一部に放射線を照射する。このとき、塗膜の一部にのみ照射する際には、例えば所定のパターンを有するフォトマスクを介して照射する。
[Step (2)]
In this step, at least a part of the coating film formed in step (1) is irradiated with radiation. At this time, when irradiating only a part of the coating film, for example, the irradiation is performed through a photomask having a predetermined pattern.
使用される放射線としては、例えば可視光線、紫外線、遠紫外線等が挙げられる。これらのうち、波長が190nm〜450nmの範囲にある放射線が好ましく、365nmの紫外線を含む放射線がより好ましい。 Examples of the radiation used include visible light, ultraviolet light, and far ultraviolet light. Among these, radiation having a wavelength in the range of 190 nm to 450 nm is preferable, and radiation including ultraviolet light of 365 nm is more preferable.
放射線照射量(露光量)は、照射される放射線の波長365nmにおける強度を照度計(OAI model 356、Optical Associates Inc.製)により測定した値として、100J/m2〜10,000J/m2が好ましく、500J/m2〜6,000J/m2がより好ましい。 Radiation dose (exposure dose), as a value measured by a luminometer intensity at a wavelength 365nm of the radiation emitted (OAI model 356, Optical Associates Ltd. Inc.), 100J / m 2 ~10,000J / m 2 is Preferably, 500 J / m 2 to 6,000 J / m 2 is more preferable.
[工程(3)]
本工程では、工程(2)で放射線が照射された塗膜を現像する。塗膜を現像することにより、不要な部分を除去して、所定のパターンを形成する。現像に使用される現像液としては、例えば水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム等の無機アルカリ、テトラメチルアンモニウムヒドロキシド、テトラエチルアンモニウムヒドロキシド等の4級アンモニウム塩等のアルカリ性化合物の水溶液等が挙げられる。上記アルカリ性化合物の水溶液には、メタノール、エタノール等の水溶性有機溶媒及び/又は界面活性剤を適当量添加してもよい。アルカリ水溶液におけるアルカリの濃度しては、適当な現像性を得る観点から、好ましくは0.1質量%以上5質量%以下である。
[Step (3)]
In this step, the coating film irradiated with radiation in step (2) is developed. By developing the coating film, unnecessary portions are removed to form a predetermined pattern. Examples of the developer used for development include inorganic alkalis such as sodium hydroxide, potassium hydroxide and sodium carbonate, and aqueous solutions of alkaline compounds such as quaternary ammonium salts such as tetramethylammonium hydroxide and tetraethylammonium hydroxide. Can be mentioned. An appropriate amount of a water-soluble organic solvent such as methanol or ethanol and / or a surfactant may be added to the aqueous solution of the alkaline compound. The concentration of alkali in the aqueous alkali solution is preferably 0.1% by mass or more and 5% by mass or less from the viewpoint of obtaining appropriate developability.
現像方法としては、例えば液盛り法、ディッピング法、シャワー法等が挙げられる。現像時間としては、常温で10秒〜180秒間程度が好ましい。現像処理に続いて、例えば流水洗浄を30秒〜90秒間行った後、圧縮空気や圧縮窒素で風乾することによって所望のパターンが得られる。 Examples of the developing method include a liquid piling method, a dipping method, and a shower method. The development time is preferably about 10 seconds to 180 seconds at room temperature. Subsequent to the development processing, for example, washing with running water is performed for 30 seconds to 90 seconds, and then a desired pattern is obtained by air drying with compressed air or compressed nitrogen.
[工程(4)]
本工程では、工程(3)で現像された塗膜に放射線を照射する。この照射により[C]感放射線性酸発生剤から酸を発生させ、発生した酸による[A]ポリオルガノシロキサンの縮合・架橋反応を促進させる。露光に使用される放射線としては、例えば可視光線、紫外線、遠紫外線、電子線、X線等が挙げられる。これらの放射線の波長としては、[B]キノンジアジド化合物の極大吸収波長より短い極大吸収波長であれば特に限定されないが、上記工程(2)で露光されなかった[B]キノンジアジド化合物への放射線照射も考慮すると、150nm〜400nmの範囲にある放射線が好ましく、300nm及び365nmの紫外線を含む放射線がより好ましい。
[Step (4)]
In this step, the coating film developed in step (3) is irradiated with radiation. By this irradiation, an acid is generated from the [C] radiation sensitive acid generator, and the condensation / crosslinking reaction of [A] polyorganosiloxane by the generated acid is promoted. Examples of radiation used for exposure include visible light, ultraviolet light, far ultraviolet light, electron beams, and X-rays. The wavelength of these radiations is not particularly limited as long as it is a maximum absorption wavelength shorter than the maximum absorption wavelength of the [B] quinonediazide compound, but radiation irradiation to the [B] quinonediazide compound that was not exposed in the above step (2) is also possible. Considering, radiation in the range of 150 nm to 400 nm is preferable, and radiation including ultraviolet rays of 300 nm and 365 nm is more preferable.
放射線照射量は、照射される放射線の波長365nmにおける強度を上記照度計により測定した値として、100J/m2〜10,000J/m2が好ましく、500J/m2〜6,000J/m2がより好ましい。 Radiation amount, the intensity at the wavelength 365nm of the radiation emitted as a value measured by the luminometer, preferably 100J / m 2 ~10,000J / m 2 , 500J / m 2 ~6,000J / m 2 is More preferred.
[工程(5)]
本工程では、工程(4)で放射線が照射された塗膜を加熱する。得られたパターン状塗膜をホットプレート、オーブン等の加熱装置により焼成(ポストベーク)することにより表示素子用層間絶縁膜を得る。焼成温度としては、120℃〜250℃が好ましい。焼成時間としては、例えばホットプレート上では5分〜30分間、オーブンでは30分〜90分間が好ましい。また、2回以上の焼成工程を行うステップベーク法等を用いることもできる。このようにして形成された表示素子用層間絶縁膜の膜厚としては、好ましくは0.1μm〜8μm、より好ましくは0.1μm〜6μm、特に好ましくは0.1μm〜4μmである。
[Step (5)]
In this step, the coating film irradiated with radiation in step (4) is heated. The obtained patterned coating film is baked (post-baked) with a heating device such as a hot plate or oven to obtain an interlayer insulating film for a display element. As a baking temperature, 120 to 250 degreeC is preferable. The firing time is preferably, for example, 5 minutes to 30 minutes on a hot plate and 30 minutes to 90 minutes in an oven. Moreover, the step baking method etc. which perform a baking process 2 times or more can also be used. The thickness of the interlayer insulating film for display element thus formed is preferably 0.1 μm to 8 μm, more preferably 0.1 μm to 6 μm, and particularly preferably 0.1 μm to 4 μm.
以下、実施例に基づき本発明を詳述するが、この実施例に本発明が限定的に解釈されるものではない。 EXAMPLES Hereinafter, although this invention is explained in full detail based on an Example, this invention is not interpreted limitedly to this Example.
<[A1]ポリオルガノシロキサンの合成>
[合成例1]
撹拌機付の容器内にプロピレングリコールモノメチルエーテル25質量部を仕込み、続いて、3−グリシドキシプロピルトリメトキシシラン(GPTMS)40質量部(31.3モル%)、メチルトリメトキシシラン(MTMS)30質量部(40.7モル%)、フェニルトリメトキシシラン(PTMS)30質量部(28.0モル%)及びシュウ酸0.5質量部を仕込み、溶液温度が60℃になるまで加熱した。溶液温度が60℃に到達後、イオン交換水18質量部を仕込み、75℃になるまで加熱し、3時間保持した。次いで脱水剤としてオルト蟻酸メチル28質量部を加え、1時間攪拌した。さらに溶液温度を40℃にし、温度を保ちながらエバポレーションすることで、イオン交換水及び加水分解縮合で発生したメタノールを除去した。以上の手順により、加水分解縮合物(A1−1)を得た。加水分解縮合物(A1−1)の固形分濃度は39.5質量%であり、Mwは3,500であり、Mw/Mnは2.0であった。
<Synthesis of [A1] polyorganosiloxane>
[Synthesis Example 1]
In a container equipped with a stirrer, 25 parts by mass of propylene glycol monomethyl ether was charged, followed by 40 parts by mass (31.3 mol%) of 3-glycidoxypropyltrimethoxysilane (GPTMS) and methyltrimethoxysilane (MTMS). 30 parts by mass (40.7 mol%), 30 parts by mass of phenyltrimethoxysilane (PTMS) (28.0 mol%) and 0.5 parts by mass of oxalic acid were charged and heated until the solution temperature reached 60 ° C. After the solution temperature reached 60 ° C., 18 parts by mass of ion-exchanged water was charged, heated to 75 ° C. and held for 3 hours. Next, 28 parts by mass of methyl orthoformate was added as a dehydrating agent and stirred for 1 hour. Furthermore, the solution temperature was set to 40 ° C., and evaporation was performed while maintaining the temperature, thereby removing ion-exchanged water and methanol generated by hydrolysis and condensation. The hydrolysis condensate (A1-1) was obtained by the above procedure. The solid content concentration of the hydrolysis-condensation product (A1-1) was 39.5% by mass, Mw was 3,500, and Mw / Mn was 2.0.
[合成例2]
撹拌機付の容器内にプロピレングリコールモノメチルエーテル25質量部を仕込み、続いて、GPTMS20質量部(16.2モル%)、MTMS15質量部(21.1モル%)、PTMS65質量部(62.7モル%)及びシュウ酸0.5質量部を仕込み、溶液温度が60℃になるまで加熱した。溶液温度が60℃に到達後、イオン交換水18質量部を仕込み、合成例1と同様の操作により、加水分解縮合物(A1−2)を得た。加水分解縮合物(A1−2)の固形分濃度は39.0質量%であり、Mwは3,400であり、Mw/Mnは2.0であった。
[Synthesis Example 2]
In a container equipped with a stirrer, 25 parts by mass of propylene glycol monomethyl ether was charged, followed by 20 parts by mass of GPTMS (16.2 mol%), 15 parts by mass of MTMS (21.1 mol%), and 65 parts by mass of PTMS (62.7 mol). %) And 0.5 part by mass of oxalic acid were charged and heated until the solution temperature reached 60 ° C. After the solution temperature reached 60 ° C., 18 parts by mass of ion-exchanged water was charged, and a hydrolysis condensate (A1-2) was obtained by the same operation as in Synthesis Example 1. The solid content concentration of the hydrolysis-condensation product (A1-2) was 39.0% by mass, Mw was 3,400, and Mw / Mn was 2.0.
[合成例3]
撹拌機付の容器内にプロピレングリコールモノメチルエーテル25質量部を仕込み、続いて、GPTMS5質量部(3.7モル%)、MTMS30質量部(38.7モル%)、PTMS65質量部(57.6モル%)及びシュウ酸0.5質量部を仕込み、溶液温度が60℃になるまで加熱した。溶液温度が60℃に到達後、イオン交換水18質量部を仕込み、合成例1と同様の操作により、加水分解縮合物(A1−3)を得た。加水分解縮合物(A1−3)の固形分濃度は39.0質量%であり、Mwは3,600であり、分子量分布(Mw/Mn)は2.0であった。
[Synthesis Example 3]
In a container equipped with a stirrer, 25 parts by mass of propylene glycol monomethyl ether was charged, followed by 5 parts by mass of GPTMS (3.7 mol%), 30 parts by mass of MTMS (38.7 mol%), and 65 parts by mass of PTMS (57.6 mol). %) And 0.5 part by mass of oxalic acid were charged and heated until the solution temperature reached 60 ° C. After the solution temperature reached 60 ° C., 18 parts by mass of ion-exchanged water was charged, and a hydrolysis condensate (A1-3) was obtained by the same operation as in Synthesis Example 1. The solid content concentration of the hydrolysis-condensation product (A1-3) was 39.0% by mass, Mw was 3,600, and the molecular weight distribution (Mw / Mn) was 2.0.
[合成例4]
撹拌機付の容器内にプロピレングリコールモノメチルエーテル25質量部を仕込み、続いて、MTMS35質量部(43.9モル%)、PTMS65質量部(56.1モル%)及びシュウ酸0.5質量部を仕込み、溶液温度が60℃になるまで加熱した。溶液温度が60℃に到達後、イオン交換水18質量部を仕込み、合成例1と同様の操作により、加水分解縮合物(A1−4)を得た。加水分解縮合物(A1−4)の固形分濃度は39.0質量%であり、Mwは3,600であり、Mw/Mnは2.0であった。
[Synthesis Example 4]
In a container equipped with a stirrer, 25 parts by mass of propylene glycol monomethyl ether was charged, followed by 35 parts by mass of MTMS (43.9 mol%), 65 parts by mass of PTMS (56.1 mol%) and 0.5 parts by mass of oxalic acid. Charged and heated until the solution temperature reached 60 ° C. After the solution temperature reached 60 ° C., 18 parts by mass of ion-exchanged water was charged, and a hydrolysis condensate (A1-4) was obtained by the same operation as in Synthesis Example 1. The solid content concentration of the hydrolysis-condensation product (A1-4) was 39.0% by mass, Mw was 3,600, and Mw / Mn was 2.0.
[合成例5]
撹拌機付の容器内にプロピレングリコールモノメチルエーテル25質量部を仕込み、続いて、2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン(ECETS)20質量部(15.0モル%)、MTMS25質量部(33.9モル%)、PTMS55質量部(51.2モル%)及びシュウ酸0.5質量部を仕込み、溶液温度が60℃になるまで加熱した。溶液温度が60℃に到達後、イオン交換水18質量部を仕込み、合成例1と同様の操作により、加水分解縮合物(A1−5)を得た。加水分解縮合物(A1−5)の固形分濃度は39.0質量%であり、Mwは3,600であり、Mw/Mnは2であった。
[Synthesis Example 5]
In a container equipped with a stirrer, 25 parts by mass of propylene glycol monomethyl ether was charged, followed by 20 parts by mass (15.0 mol%) of 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane (EMETS), and 25 masses of MTMS. Parts (33.9 mol%), PTMS 55 parts by mass (51.2 mol%) and oxalic acid 0.5 parts by mass were heated until the solution temperature reached 60 ° C. After the solution temperature reached 60 ° C., 18 parts by mass of ion-exchanged water was charged, and a hydrolysis condensate (A1-5) was obtained by the same operation as in Synthesis Example 1. The solid content concentration of the hydrolysis-condensation product (A1-5) was 39.0% by mass, Mw was 3,600, and Mw / Mn was 2.
<[A2]ポリオルガノシロキサンの合成>
[合成例6]
撹拌機、温度計、滴下漏斗及び還流冷却管を備えた反応容器に、ECETS100質量部(100.0モル%)、メチルイソブチルケトン500質量部及びトリエチルアミン10質量部を仕込み、室温で混合した。次いで、脱イオン水100質量部を滴下漏斗より30分かけて滴下した後、還流下で混合しつつ、80℃で6時間反応させた。反応終了後、有機層を取り出し、0.2質量%硝酸アンモニウム水溶液により洗浄後の水が中性になるまで洗浄した後、減圧下で溶媒及び水を留去することにより、加水分解縮合物(A2−1)を粘稠な透明液体として得た。この加水分解縮合物(A2−1)について、1H−NMR分析を行なったところ、化学シフト(δ)=3.2ppm付近にエポキシ基に基づくピークが理論強度どおりに得られ、反応中にエポキシ基の副反応が起こっていないことが確認された。得られた加水分解縮合物(A2−1)のMwは4,000であり、Mw/Mnは2.0であった。
<Synthesis of [A2] polyorganosiloxane>
[Synthesis Example 6]
In a reaction vessel equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser, 100 parts by mass (100.0 mol%) of ECETS, 500 parts by mass of methyl isobutyl ketone and 10 parts by mass of triethylamine were charged and mixed at room temperature. Next, 100 parts by mass of deionized water was dropped from the dropping funnel over 30 minutes, and the mixture was reacted at 80 ° C. for 6 hours while mixing under reflux. After completion of the reaction, the organic layer was taken out and washed with 0.2% by mass aqueous ammonium nitrate solution until the water after washing became neutral, and then the hydrolysis condensate (A2) was removed by distilling off the solvent and water under reduced pressure. -1) was obtained as a viscous transparent liquid. This hydrolyzed condensate (A2-1) was subjected to 1 H-NMR analysis. As a result, a peak based on an epoxy group was obtained in the vicinity of chemical shift (δ) = 3.2 ppm in accordance with the theoretical intensity. It was confirmed that no side reaction of the group occurred. Mw of the obtained hydrolysis-condensation product (A2-1) was 4,000, and Mw / Mn was 2.0.
[合成例7]
撹拌機、温度計、滴下漏斗及び還流冷却管を備えた反応容器に、ECETS80質量部(68.9モル%)、MTMS20質量部(31.1モル%)、メチルイソブチルケトン500質量部及びトリエチルアミン10質量部を仕込み、室温で混合した。次いで合成例6と同様の操作により、加水分解縮合物(A2−2)を粘稠な透明液体として得た。この加水分解縮合物(A2−2)について、1H−NMR分析を行なったところ、エポキシ基に基づくピークが確認された。得られた加水分解縮合物(A2−2)のMwは3,800であり、Mw/Mnは2.0であった。
[Synthesis Example 7]
In a reaction vessel equipped with a stirrer, thermometer, dropping funnel and reflux condenser, ECETS 80 parts by mass (68.9 mol%), MTMS 20 parts by mass (31.1 mol%), methyl isobutyl ketone 500 parts by mass and triethylamine 10 A mass part was charged and mixed at room temperature. Subsequently, the hydrolysis condensate (A2-2) was obtained as a viscous transparent liquid by the same operation as in Synthesis Example 6. About this hydrolysis-condensation product (A2-2), when the 1 H-NMR analysis was conducted, the peak based on an epoxy group was confirmed. Mw of the obtained hydrolysis-condensation product (A2-2) was 3,800, and Mw / Mn was 2.0.
[合成例8]
撹拌機、温度計、滴下漏斗及び還流冷却管を備えた反応容器に、ECETS60質量部(54.7モル%)、MTMS20質量部(30.4モル%)、テトラエトキシシラン20質量部(14.9モル%)、メチルイソブチルケトン500質量部及びトリエチルアミン10質量部を仕込み、室温で混合した。次いで合成例6と同様の操作により、加水分解縮合物(A2−3)を粘稠な透明液体として得た。この加水分解縮合物(A2−3)について、1H−NMR分析を行なったところ、エポキシ基に基づくピークが確認された。得られた加水分解縮合物(A2−3)のMwは4,500であり、Mw/Mnは2.0であった。
[Synthesis Example 8]
In a reaction vessel equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser, 60 parts by mass of ECETS (54.7 mol%), 20 parts by mass of MTMS (30.4 mol%), 20 parts by mass of tetraethoxysilane (14. 9 mol%), 500 parts by mass of methyl isobutyl ketone and 10 parts by mass of triethylamine were charged and mixed at room temperature. Subsequently, the hydrolysis condensate (A2-3) was obtained as a viscous transparent liquid by the same operation as in Synthesis Example 6. About this hydrolysis-condensation product (A2-3), when the 1 H-NMR analysis was conducted, the peak based on an epoxy group was confirmed. Mw of the obtained hydrolysis-condensation product (A2-3) was 4,500, and Mw / Mn was 2.0.
[合成例9]
撹拌機、温度計、滴下漏斗及び還流冷却管を備えた反応容器に、GPTMS100質量部(100.0モル%)、メチルイソブチルケトン500質量部及びトリエチルアミン10質量部を仕込み、室温で混合した。次いで、合成例6と同様の操作により、加水分解縮合物(A2−4)を粘稠な透明液体として得た。この加水分解縮合物(A2−4)について、1H−NMR分析を行なったところ、エポキシ基に基づくピークが確認された。得られた加水分解縮合物(A2−4)のMwは5,000であり、Mw/Mnは2.0であった。
[Synthesis Example 9]
In a reaction vessel equipped with a stirrer, thermometer, dropping funnel and reflux condenser, 100 parts by mass (100.0 mol%) of GPTMS, 500 parts by mass of methyl isobutyl ketone and 10 parts by mass of triethylamine were charged and mixed at room temperature. Subsequently, the hydrolysis condensate (A2-4) was obtained as a viscous transparent liquid by the same operation as in Synthesis Example 6. About this hydrolysis-condensation product (A2-4), when the 1 H-NMR analysis was conducted, the peak based on an epoxy group was confirmed. Mw of the obtained hydrolysis-condensation product (A2-4) was 5,000, and Mw / Mn was 2.0.
<ポジ型感放射線性樹脂組成物の調製>
実施例及び比較例で使用した各成分の詳細を示す。
<Preparation of positive radiation sensitive resin composition>
The detail of each component used in the Example and the comparative example is shown.
<[B]キノンジアジド化合物>
B−1:4,4’−[1−[4−[1−(4−ヒドロキシフェニル)−1−メチルエチル]フェニル]エチリデン]ビスフェノール(1.0モル)と1,2−ナフトキノンジアジド−5−スルホン酸クロリド(3.0モル)との縮合物
B−2:1,1,1−トリ(p−ヒドロキシフェニル)エタン(1.0モル)と1,2−ナフトキノンジアジド−5−スルホン酸クロリド(3.0モル)との縮合物
<[B] quinonediazide compound>
B-1: 4,4 ′-[1- [4- [1- (4-hydroxyphenyl) -1-methylethyl] phenyl] ethylidene] bisphenol (1.0 mol) and 1,2-naphthoquinonediazide-5 -Condensate B-2 with sulfonic acid chloride (3.0 mol): 1,1,1-tri (p-hydroxyphenyl) ethane (1.0 mol) and 1,2-naphthoquinonediazide-5-sulfonic acid Condensate with chloride (3.0 mol)
<[C]感放射線性酸発生剤>
C−1:1−(4,7−ジブトキシ−1−ナフタレニル)テトラヒドロチオフェニウムトリフルオロメタンスルホナート
C−2:ジフェニル(4−(フェニルチオ)フェニル)スルホニウムトリフルオロトリスペンタフルオロエチルホスファート
<[C] Radiation sensitive acid generator>
C-1: 1- (4,7-dibutoxy-1-naphthalenyl) tetrahydrothiophenium trifluoromethanesulfonate C-2: Diphenyl (4- (phenylthio) phenyl) sulfonium trifluorotrispentafluoroethyl phosphate
[実施例1]
[A1]ポリオルガノシロキサンとして加水分解縮合物(A1−1)を含む溶液(加水分解縮合物(A1−1)50質量部(固形分)に相当する量)に、[A2]ポリオルガノシロキサンとして加水分解縮合物(A2−3)50質量部、[B]キノンジアジド化合物として(B−1)10質量部、[C]感放射線性酸発生剤として(C−1)2質量部、界面活性剤としてシリコーン系界面活性剤(東レ・ダウコーニング製、SH 8400 FLUID)0.1質量部を加え、ポジ型感放射線性樹脂組成物を調製した。
[Example 1]
[A1] In a solution containing hydrolyzed condensate (A1-1) as polyorganosiloxane (amount corresponding to 50 parts by mass (solid content) of hydrolyzed condensate (A1-1)), [A2] Hydrolysis condensate (A2-3) 50 parts by mass, [B] 10 parts by mass of quinonediazide compound, [C] 2 parts by mass of (C-1) as a radiation sensitive acid generator, surfactant A silicone type surfactant (manufactured by Dow Corning Toray, SH 8400 FLUID) 0.1 part by mass was added as a positive radiation sensitive resin composition.
[実施例2〜10及び比較例1〜5]
表1に示す種類、量の各成分を使用したこと以外は実施例1と同様に操作し、各ポジ型感放射線性樹脂組成物を調製した。なお、表1中の「−」は該当する成分を使用しなかったことを表す。
[Examples 2 to 10 and Comparative Examples 1 to 5]
Each positive type radiation sensitive resin composition was prepared in the same manner as in Example 1 except that each type and amount of components shown in Table 1 were used. In Table 1, “-” indicates that the corresponding component was not used.
<評価>
調製した各ポジ型感放射線性樹脂組成物を用いて以下のようにポジ型感放射線性樹脂組成物及び層間絶縁膜としての特性を評価した。結果を表1にあわせて示す。
<Evaluation>
The characteristics as a positive radiation sensitive resin composition and an interlayer insulating film were evaluated using the prepared positive radiation sensitive resin compositions as follows. The results are shown in Table 1.
[感度(J/m2)]
シリコン基板上に、調製した各ポジ型感放射線性樹脂組成物をスピンナーにより塗布した後、100℃にて2分間ホットプレート上でプレベークすることにより膜厚4.0μmの塗膜を形成した。なお、実施例4については、スリットダイコーターを用いてポジ型感放射線性樹脂組成物を塗布した後、室温で15秒かけて0.5Torrまで減圧し、溶媒を除去した後、100℃にて2分間ホットプレート上でプレベークすることにより膜厚4.0μmの塗膜を形成した。得られた塗膜に対し、露光機(365nmの超高圧水銀ランプ、キヤノン製、PLA−501F)を用い、6.0μmのライン・アンド・スペース(1対1)のパターンを有するマスクを介して露光時間を変化させて露光を行った後、2.38質量%のテトラメチルアンモニウムヒドロキシド水溶液にて25℃、80秒間、液盛り法で現像した。次いで、超純水で1分間流水洗浄を行い、乾燥させてシリコン基板上にパターンを形成した。このとき、スペース線幅(底部)が6.0μmとなるのに必要な最小露光量を測定した。この最小露光量を放射線感度(J/m2)とした。最小露光量が800(J/m2)以下の時、感度は良好と判断した。
[Sensitivity (J / m 2 )]
Each positive type radiation sensitive resin composition thus prepared was applied onto a silicon substrate with a spinner, and then prebaked on a hot plate at 100 ° C. for 2 minutes to form a coating film having a thickness of 4.0 μm. In Example 4, after applying the positive radiation sensitive resin composition using a slit die coater, the pressure was reduced to 0.5 Torr over 15 seconds at room temperature, and the solvent was removed. A coating film having a film thickness of 4.0 μm was formed by pre-baking on a hot plate for 2 minutes. For the obtained coating film, using an exposure machine (365 nm ultra-high pressure mercury lamp, manufactured by Canon, PLA-501F), through a mask having a 6.0 μm line-and-space (one-to-one) pattern. After performing exposure while changing the exposure time, the film was developed with a 2.38 mass% tetramethylammonium hydroxide aqueous solution at 25 ° C. for 80 seconds by a puddle method. Next, running water was washed with ultrapure water for 1 minute and dried to form a pattern on the silicon substrate. At this time, the minimum exposure amount necessary for the space line width (bottom) to be 6.0 μm was measured. This minimum exposure amount was defined as radiation sensitivity (J / m 2 ). When the minimum exposure amount was 800 (J / m 2 ) or less, the sensitivity was judged to be good.
[耐メルトフロー性(μm)]
上記感度の評価と同様に操作して、スペース線幅(底部)が6.0μmとなるパターンを形成した。得られたパターンに、上記露光機を用いて、積算照射量が3,000J/m2となるように露光を行った後、クリーンオーブン内にて220℃で1時間加熱することによりポストベークを行い表示素子の層間絶縁膜を形成した。さらに、230℃で10分間加熱して、層間絶縁膜をメルトフローさせ、SEM(走査型電子顕微鏡)により層間絶縁膜底部の寸法を測定した。この時、層間絶縁膜底部の寸法が6.35μm未満であるとき、耐メルトフロー性(μm)が良好であると判断した。一方、層間絶縁膜底部の寸法が6.35μm以上の場合、耐メルトフロー性が不良であると判断した。
[Melt flow resistance (μm)]
A pattern having a space line width (bottom) of 6.0 μm was formed in the same manner as in the sensitivity evaluation. The obtained pattern was exposed using the above exposure machine so that the integrated irradiation amount was 3,000 J / m 2, and then post-baked by heating at 220 ° C. for 1 hour in a clean oven. Then, an interlayer insulating film of the display element was formed. Furthermore, it heated at 230 degreeC for 10 minute (s), the interlayer insulation film was made to melt flow, and the dimension of the interlayer insulation film bottom part was measured by SEM (scanning electron microscope). At this time, when the dimension of the bottom portion of the interlayer insulating film was less than 6.35 μm, it was judged that the melt flow resistance (μm) was good. On the other hand, when the dimension of the bottom of the interlayer insulating film was 6.35 μm or more, it was determined that the melt flow resistance was poor.
[耐溶媒性(%)]
上記感度の評価において、露光をしなかった以外は、同様に操作してシリコン基板上に塗膜を形成した。得られた塗膜に、それぞれ上記露光機を用いて、積算照射量が3,000J/m2となるように露光を行った後、クリーンオーブン内にて220℃で1時間加熱することにより層間絶縁膜を得た。得られた硬化膜の膜厚(T1)を測定した。そして、この層間絶縁膜が形成されたシリコン基板を70℃に温度制御されたジメチルスルホキシド中に20分間浸漬した後、層間絶縁膜の膜厚(t1)を測定し、浸漬による膜厚変化率を下記式から算出し耐溶媒性(%)とした。
(|t1−T1|/T1)×100(%)
膜厚変化率が4%以下の時、耐溶剤性は良好と判断した。なお、耐溶媒性の評価においては、形成する膜のパターニングは不要のため、現像工程を省略し、塗膜形成工程、放射線照射工程及び加熱工程のみを行い評価に供した。
[Solvent resistance (%)]
In the evaluation of the sensitivity, a coating film was formed on the silicon substrate in the same manner except that no exposure was performed. Each of the obtained coating films was exposed using the above-described exposure machine so that the integrated irradiation amount was 3,000 J / m 2, and then heated at 220 ° C. for 1 hour in a clean oven. An insulating film was obtained. The film thickness (T1) of the obtained cured film was measured. Then, after immersing the silicon substrate on which the interlayer insulating film is formed in dimethyl sulfoxide whose temperature is controlled at 70 ° C. for 20 minutes, the thickness (t1) of the interlayer insulating film is measured, and the rate of change in film thickness due to the immersion is measured. The solvent resistance (%) was calculated from the following formula.
(| T1-T1 | / T1) × 100 (%)
When the film thickness change rate was 4% or less, the solvent resistance was judged to be good. In the evaluation of the solvent resistance, the patterning of the film to be formed is unnecessary, so the development step was omitted, and only the coating film forming step, the radiation irradiation step, and the heating step were performed for evaluation.
[耐熱性(%)]
上記耐溶媒性の評価と同様に操作してシリコン基板上に層間絶縁膜を形成し、得られた層間絶縁膜の膜厚(T2)を測定した。次いで、この層間絶縁膜が形成されたシリコン基板を、クリーンオーブン内にて240℃で1時間追加ベークした後、当該層間絶縁膜の膜厚(t2)を測定し、追加ベークによる膜厚変化率を下記式から算出し耐熱性(%)とした。
(|t2−T2|/T2)×100(%)
膜厚変化率が3%未満の時、耐熱性は良好であると判断した。
[Heat-resistant(%)]
An interlayer insulating film was formed on the silicon substrate by operating in the same manner as in the evaluation of the solvent resistance, and the film thickness (T2) of the obtained interlayer insulating film was measured. Next, the silicon substrate on which the interlayer insulating film is formed is additionally baked at 240 ° C. for 1 hour in a clean oven, and then the film thickness (t2) of the interlayer insulating film is measured, and the film thickness change rate due to the additional baking. Was calculated from the following formula and defined as heat resistance (%).
(| T2-T2 | / T2) × 100 (%)
When the film thickness change rate was less than 3%, it was judged that the heat resistance was good.
[電圧保持率(%)]
表面にナトリウムイオンの溶出を防止するSiO2膜が形成され、さらにITO(インジウム−酸化錫合金)電極を所定形状に蒸着したソーダガラス基板上に、スピンナーを用いて各ポジ型感放射線性樹脂組成物を塗布し、100℃のホットプレート上で2分間プレベークを行って、膜厚2.0μmの塗膜を形成した。2.38重量%のテトラメチルアンモニウムヒドロキシド水溶液にて、25℃、80秒間、ディップ法による現像を行った。次いで、フォトマスクを介さずに、塗膜に積算照射量が3,000J/m2となるように露光を行った。その後、さらに、220℃で1時間ポストベークを行い硬化膜を形成した。次いで、この硬化膜を有する基板上に5.5μm径のビーズスペーサーを散布後、これと表面にITO電極を所定形状に蒸着しただけのソーダガラス基板とを対向させた状態で、液晶注入口を残して4辺を0.8mmのガラスビーズを混合したシール剤を用いて貼り合わせ、液晶(メルク製、MLC6608)を注入した後に液晶注入口を封止することにより、液晶セルを作製した。この液晶セルを60℃の恒温層に入れて、液晶セルの電圧保持率を、液晶電圧保持率測定システム(VHR−1A型、東陽テクニカ製)により印加電圧5.5Vの方形波、測定周波数60Hzの条件で測定した。なお、ここで電圧保持率(%)とは、下記式から算出される値である。
電圧保持率=(基準時から16.7ミリ秒後の液晶セル電位差)/(0ミリ秒で印加した電圧)×100(%)
液晶セルの電圧保持率が95%以下の時、液晶パネル形成時に「焼き付き」と呼ばれる不具合を起こす可能性が高くなる。
[Voltage holding ratio (%)]
Each positive-type radiation-sensitive resin composition using a spinner is formed on a soda glass substrate on which a SiO 2 film for preventing elution of sodium ions is formed on the surface and an ITO (indium-tin oxide alloy) electrode is deposited in a predetermined shape. The product was applied and prebaked on a hot plate at 100 ° C. for 2 minutes to form a coating film having a thickness of 2.0 μm. Development was carried out by a dip method in a 2.38 wt% tetramethylammonium hydroxide aqueous solution at 25 ° C. for 80 seconds. Next, the coating film was exposed to 3,000 J / m 2 without using a photomask. Thereafter, post-baking was further performed at 220 ° C. for 1 hour to form a cured film. Next, after spraying a 5.5 μm diameter bead spacer on the substrate having the cured film, a liquid crystal injection port is placed in a state where this is opposed to a soda glass substrate on which the ITO electrode is deposited in a predetermined shape. The remaining four sides were bonded together using a sealant mixed with 0.8 mm glass beads, and after injecting liquid crystal (MLC, MLC6608), the liquid crystal injection port was sealed to prepare a liquid crystal cell. This liquid crystal cell was put in a constant temperature layer of 60 ° C., and the voltage holding ratio of the liquid crystal cell was measured by a liquid crystal voltage holding ratio measuring system (VHR-1A type, manufactured by Toyo Technica Co., Ltd.), a square wave with an applied voltage of 5.5 V, a measuring frequency of 60 Hz It measured on condition of this. Here, the voltage holding ratio (%) is a value calculated from the following equation.
Voltage holding ratio = (potential difference of liquid crystal cell after 16.7 milliseconds from the reference time) / (voltage applied at 0 milliseconds) × 100 (%)
When the voltage holding ratio of the liquid crystal cell is 95% or less, there is a high possibility of causing a problem called “burn-in” when forming the liquid crystal panel.
表1の結果から本発明のポジ型感放射線性樹脂組成物は感度に優れることがわかった。また、当該ポジ型感放射線性樹脂組成物から形成される層間絶縁膜は、耐メルトフロー性、耐溶媒性及び耐熱性に優れると共に、優れた電圧保持率を有する表示素子が得られることが分かった。 From the results in Table 1, it was found that the positive radiation sensitive resin composition of the present invention was excellent in sensitivity. In addition, it was found that the interlayer insulating film formed from the positive radiation sensitive resin composition is excellent in melt flow resistance, solvent resistance and heat resistance, and a display element having an excellent voltage holding ratio can be obtained. It was.
本発明のポジ型感放射線性樹脂組成物は、十分な感度を有し、これを用いた層間絶縁膜の耐メルトフロー性、耐熱性及び耐溶媒性を高め、電圧保持率を向上し、液晶表示素子(LCD)や有機EL表示素子等の表示素子の層間絶縁膜、平坦化膜、隔壁材等の硬化膜、タッチパネル用保護幕を形成するための材料として好適に使用できる。 The positive-type radiation-sensitive resin composition of the present invention has sufficient sensitivity, improves the melt flow resistance, heat resistance and solvent resistance of the interlayer insulating film using the composition, improves the voltage holding ratio, and the liquid crystal It can be suitably used as a material for forming an interlayer insulating film of a display element such as a display element (LCD) or an organic EL display element, a flattened film, a cured film such as a partition material, and a protective curtain for a touch panel.
Claims (9)
[A2]上記含有割合が、50モル%以上100モル%以下であるポリオルガノシロキサン
を含有するポジ型感放射線性樹脂組成物。 [A1] Among the organic groups bonded to the silicon atom by a carbon atom, the content ratio of the organic group having an epoxy group is 0 mol% or more and less than 50 mol%, and [A2] the content ratio is A positive-type radiation-sensitive resin composition containing a polyorganosiloxane that is 50 mol% or more and 100 mol% or less.
(2)工程(1)で形成した塗膜の少なくとも一部に放射線を照射する工程、
(3)工程(2)で放射線が照射された塗膜を現像する工程、
(4)工程(3)で現像された塗膜に放射線を照射する工程、及び
(5)工程(4)で放射線が照射された塗膜を加熱する工程
を有する表示素子用層間絶縁膜の形成方法。 (1) The process of forming the coating film of the positive radiation sensitive resin composition of Claim 7 on a board | substrate,
(2) A step of irradiating at least a part of the coating film formed in step (1),
(3) A step of developing the coating film irradiated with radiation in step (2),
(4) Forming an interlayer insulating film for a display element, comprising: irradiating the coating film developed in step (3) with radiation; and (5) heating the coating film irradiated with radiation in step (4). Method.
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