JP2010060957A - 感光性組成物、それから形成された硬化膜、および硬化膜を有する素子 - Google Patents
感光性組成物、それから形成された硬化膜、および硬化膜を有する素子 Download PDFInfo
- Publication number
- JP2010060957A JP2010060957A JP2008227825A JP2008227825A JP2010060957A JP 2010060957 A JP2010060957 A JP 2010060957A JP 2008227825 A JP2008227825 A JP 2008227825A JP 2008227825 A JP2008227825 A JP 2008227825A JP 2010060957 A JP2010060957 A JP 2010060957A
- Authority
- JP
- Japan
- Prior art keywords
- group
- polysiloxane
- cured film
- compound
- photosensitive composition
- 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.)
- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 59
- -1 polysiloxane Polymers 0.000 claims abstract description 133
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 72
- 239000002904 solvent Substances 0.000 claims abstract description 20
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000001282 organosilanes Chemical class 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 238000002834 transmittance Methods 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 39
- 230000035945 sensitivity Effects 0.000 abstract description 17
- 239000010408 film Substances 0.000 description 86
- 239000000243 solution Substances 0.000 description 42
- 150000001875 compounds Chemical class 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- 229920000178 Acrylic resin Polymers 0.000 description 23
- 239000004925 Acrylic resin Substances 0.000 description 23
- 239000002253 acid Substances 0.000 description 23
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 22
- 239000002245 particle Substances 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- 239000000463 material Substances 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 238000000034 method Methods 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000004132 cross linking Methods 0.000 description 13
- 238000011161 development Methods 0.000 description 13
- 238000010438 heat treatment Methods 0.000 description 13
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 12
- 238000004061 bleaching Methods 0.000 description 12
- 230000018109 developmental process Effects 0.000 description 12
- 239000002612 dispersion medium Substances 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 11
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000003431 cross linking reagent Substances 0.000 description 9
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 238000001029 thermal curing Methods 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 230000007423 decrease Effects 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 229920001187 thermosetting polymer Polymers 0.000 description 8
- 239000006087 Silane Coupling Agent Substances 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 7
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 7
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 7
- 238000009834 vaporization Methods 0.000 description 7
- 230000008016 vaporization Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 239000011229 interlayer Substances 0.000 description 5
- 239000003456 ion exchange resin Substances 0.000 description 5
- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- 230000001476 alcoholic effect Effects 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 150000004756 silanes Chemical class 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000501754 Astronotus ocellatus Species 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 125000003566 oxetanyl group Chemical group 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 238000011907 photodimerization Methods 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 3
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- APQSQLNWAIULLK-UHFFFAOYSA-N 1,4-dimethylnaphthalene Chemical compound C1=CC=C2C(C)=CC=C(C)C2=C1 APQSQLNWAIULLK-UHFFFAOYSA-N 0.000 description 2
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- AHNLTPNNRFETEC-UHFFFAOYSA-N 2-(3-trimethoxysilylpropyl)butanedioic acid Chemical compound CO[Si](OC)(OC)CCCC(C(O)=O)CC(O)=O AHNLTPNNRFETEC-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- BNDRWEVUODOUDW-UHFFFAOYSA-N 3-Hydroxy-3-methylbutan-2-one Chemical compound CC(=O)C(C)(C)O BNDRWEVUODOUDW-UHFFFAOYSA-N 0.000 description 2
- LMIOYAVXLAOXJI-UHFFFAOYSA-N 3-ethyl-3-[[4-[(3-ethyloxetan-3-yl)methoxymethyl]phenyl]methoxymethyl]oxetane Chemical compound C=1C=C(COCC2(CC)COC2)C=CC=1COCC1(CC)COC1 LMIOYAVXLAOXJI-UHFFFAOYSA-N 0.000 description 2
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-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
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- LBQJFQVDEJMUTF-UHFFFAOYSA-N 9,10-dipropoxyanthracene Chemical compound C1=CC=C2C(OCCC)=C(C=CC=C3)C3=C(OCCC)C2=C1 LBQJFQVDEJMUTF-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- RNMZLZXQSIWDGV-UHFFFAOYSA-N C(C)C1(COC1)COC(C)O[Si](OCC)(OCC)CCC Chemical compound C(C)C1(COC1)COC(C)O[Si](OCC)(OCC)CCC RNMZLZXQSIWDGV-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000003377 acid catalyst Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- XGZGKDQVCBHSGI-UHFFFAOYSA-N butyl(triethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)OCC XGZGKDQVCBHSGI-UHFFFAOYSA-N 0.000 description 2
- SXPLZNMUBFBFIA-UHFFFAOYSA-N butyl(trimethoxy)silane Chemical compound CCCC[Si](OC)(OC)OC SXPLZNMUBFBFIA-UHFFFAOYSA-N 0.000 description 2
- 238000005253 cladding Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-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
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 2
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 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
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
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- ADLSSRLDGACTEX-UHFFFAOYSA-N tetraphenyl silicate Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 ADLSSRLDGACTEX-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
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- 239000012780 transparent material Substances 0.000 description 1
- YZVRVDPMGYFCGL-UHFFFAOYSA-N triacetyloxysilyl acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)OC(C)=O YZVRVDPMGYFCGL-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
- ZQJYXISBATZORI-UHFFFAOYSA-N tributyl(ethoxy)silane Chemical compound CCCC[Si](CCCC)(CCCC)OCC ZQJYXISBATZORI-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- WUMSTCDLAYQDNO-UHFFFAOYSA-N triethoxy(hexyl)silane Chemical compound CCCCCC[Si](OCC)(OCC)OCC WUMSTCDLAYQDNO-UHFFFAOYSA-N 0.000 description 1
- BOVWGKNFLVZRDU-UHFFFAOYSA-N triethoxy(trifluoromethyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)F BOVWGKNFLVZRDU-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
- ORVBHOQTQDOUIW-UHFFFAOYSA-N trimethoxy(trifluoromethyl)silane Chemical compound CO[Si](OC)(OC)C(F)(F)F ORVBHOQTQDOUIW-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- XJMULQBEYKPFGJ-UHFFFAOYSA-N trimethyl-[2-[10-(2-trimethylsilylethynyl)anthracen-9-yl]ethynyl]silane Chemical compound C1=CC=C2C(C#C[Si](C)(C)C)=C(C=CC=C3)C3=C(C#C[Si](C)(C)C)C2=C1 XJMULQBEYKPFGJ-UHFFFAOYSA-N 0.000 description 1
- PBRKCNMSBIMTKC-UHFFFAOYSA-N triphenyl-(10-triphenylsilylanthracen-9-yl)silane Chemical compound C1=CC=CC=C1[Si](C=1C2=CC=CC=C2C(=C2C=CC=CC2=1)[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 PBRKCNMSBIMTKC-UHFFFAOYSA-N 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
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- 230000002087 whitening effect Effects 0.000 description 1
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Abstract
【解決手段】(a)ポリシロキサン、(b)ナフトキノンジアジド化合物、(c)4級アンモニウム塩、(d)溶剤を含有するポジ型感光性組成物。
【選択図】 なし
Description
一方、高耐熱性、高透明性、高耐薬品性といった特性を有する他の材料として、ポリシロキサンが知られており、これにポジ型の感光性を付与するためにキノンジアジド化合物を組み合わせた材料(特許文献5参照)が公知である。この材料は透明性が高く、基板の高温処理によっても透明性は低下すること無く、高透明の硬化膜を得ることができる。しかしながら、この材料に於いても、感度、解像度や耐薬品性は十分とは言えない。
ここで、(a)のポリシロキサンは、下記一般式(1)で表されるオルガノシランの1種以上を加水分解し縮合させることによって合成されるポリシロキサンであることが好ましい。
一般式(2)で表されるオルガノシランの具体例としては、メチルシリケート51(扶桑化学工業株式会社製)、Mシリケート51、シリケート40、シリケート45(多摩化学工業株式会社製)、メチルシリケート51、メチルシリケート53A、エチルシリケート40、エチルシリケート48(コルコート株式会社製)などが挙げられる。
4級アンモニウム塩の添加量は、特に制限されないが、耐薬品性およびパターン形成時の感度の観点から樹脂(ポリシロキサン)100重量部に対して0.01〜10重量部であることが好ましく、より好ましくは0.05〜5重量部である。
中でも、基板密着性や組成物の保存安定性の点から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が好ましく使用される。
界面活性剤の含有量は、感光性組成物中、0.0001〜1重量%とするのが一般的である。
架橋剤の添加量は特に制限されないが、好ましくは樹脂(ポリシロキサン+アクリル樹脂)100重量部に対して0.1〜10重量部の範囲である。架橋剤の添加量が0.1重量部より少ないと、樹脂の架橋が不十分で効果が少ない。一方、架橋剤の添加量が10重量部より多いと、硬化膜の無色透明性が低下したり、組成物の貯蔵安定性が低下する。
架橋促進剤の添加量は、特に制限は無いが、好ましくは樹脂(ポリシロキサン)100重量部に対して0.01〜5重量部の範囲である。添加量が0.01重量部より少ないと効果が十分ではなく、5重量部より多いとプリベーク時やパターン露光時にポリシロキサンの架橋が起こる場合がある。
PGMEA:プロピレングリコールモノメチルエーテルアセテート
GBL:γ−ブチロラクトン
EDM:ジエチレングリコールメチルエチルエーテル
また、ポリシロキサン溶液、アクリル樹脂溶液の固形分濃度、およびポリシロキサン、アクリル樹脂の重量平均分子量(Mw)は、以下の通り求めた。
アルミカップにポリシロキサン溶液またはアクリル樹脂溶液を1g秤取し、ホットプレートを用いて250℃で30分間加熱して液分を蒸発させた。加熱後のアルミカップに残った固形分を秤量して、アクリル樹脂またはポリシロキサン溶液の固形分濃度を求めた。
重量平均分子量はGPC(Waters社製410型RI検出器、流動層:テトラヒドロフラン)にてポリスチレン換算により求めた。
500mlの三口フラスコにメチルトリメトキシシランを54.48g(0.40mol)、フェニルトリメトキシシランを109.07g(0.55mol)、(2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシランを12.32g(0.05mol)、DAAを160g仕込み、室温で攪拌しながら水55gにリン酸0.53g(仕込みモノマーに対して0.3重量%)を溶かしたリン酸水溶液を10分かけて添加した。その後、フラスコを40℃のオイルバスに浸けて30分攪拌した後、オイルバスを30分かけて115℃まで昇温した。昇温開始1時間後に溶液の内温が100℃に到達し、そこから2時間加熱攪拌し(内温は100〜110℃)、ポリシロキサン溶液(a)を得た。なお、加熱攪拌中、窒素を0.05l(リットル)/min流した。反応中に副生成物であるメタノール、水、および溶媒が合計132g留出した。
500mlの三口フラスコにメチルトリメトキシシランを27.24g(0.20mol)、フェニルトリメトキシシランを109.07g(0.55mol)、(2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシランを12.32g(0.05mol)、Mシリケート51(多摩化学工業株式会社製)を23.50g(0.20mol)、PGMEAを157g仕込み、室温で攪拌しながら水53gにリン酸0.52g(仕込みモノマーに対して0.3重量%)を溶かしたリン酸水溶液を10分かけて添加した。その後、フラスコを40℃のオイルバスに浸けて30分攪拌した後、オイルバスを30分かけて115℃まで昇温した。昇温開始1時間後に溶液の内温が100℃に到達し、そこから2時間加熱攪拌し(内温は100〜110℃)、ポリシロキサン溶液(b)を得た。なお、加熱攪拌中、窒素を0.05l(リットル)/min流した。反応中に副生成物であるメタノール、水および溶媒が合計125g留出した。
500mlの三口フラスコにメチルトリメトキシシランを61.29g(0.45mol)、フェニルトリメトキシシランを89.24g(0.45mol)、シリカゾル粒子分散液クォートロンPL−2L(扶桑化学工業株式会社製、分散媒:水 シリカ粒子含有量19.7w%)30.50g(0.10mol)、DAA190gを仕込み、室温で攪拌しながら水24.11gにリン酸0.47g(仕込みモノマーに対して0.3重量%)を溶かしたリン酸水溶液を10分かけて添加した。その後、フラスコを40℃のオイルバスに浸けて30分攪拌した後、オイルバスを30分かけて115℃まで昇温した。昇温開始1時間後に溶液の内温が100℃に到達し、そこから2時間加熱攪拌し(内温は100〜110℃)、ポリシロキサン溶液(c)を得た。なお、加熱攪拌中、窒素を0.05l(リットル)/min流した。反応中に副生成物であるメタノール、水および溶媒が合計112g留出した。
500mlの三口フラスコにメチルトリメトキシシランを43.58g(0.32mol)、フェニルトリメトキシシランを118.98g(0.60mol)、(2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシランを12.32g(0.05mol)、Mシリケート51(多摩化学工業株式会社製)を3.53g(0.03mol)、PGMEAを163g仕込み、室温で攪拌しながら水55gにリン酸1.07g(仕込みモノマーに対して0.6重量%)を溶かしたリン酸水溶液を10分かけて添加した。その後、フラスコを40℃のオイルバスに浸けて30分攪拌した後、オイルバスを30分かけて115℃まで昇温した。昇温開始1時間後に溶液の内温が100℃に到達し、そこから2時間加熱攪拌し(内温は100〜110℃)、ポリシロキサン溶液(d)を得た。なお、加熱攪拌中、窒素を0.05l(リットル)/min流した。反応中に副生成物であるメタノール、水および溶媒が合計124g留出した。
500mlの三口フラスコにメチルトリメトキシシランを40.86g(0.30mol)、フェニルトリメトキシシランを118.98g(0.60mol)、(2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシランを24.64g(0.10mol)、PGMEAを170g仕込み、室温で攪拌しながら水56gにリン酸0.55g(仕込みモノマーに対して0.3重量%)を溶かしたリン酸水溶液を10分かけて添加した。その後、フラスコを40℃のオイルバスに浸けて30分攪拌した後、オイルバスを30分かけて115℃まで昇温した。昇温開始1時間後に溶液の内温が100℃に到達し、そこから2時間加熱攪拌し(内温は100〜110℃)、ポリシロキサン溶液(e)を得た。なお、加熱攪拌中、窒素を0.05l(リットル)/min流した。反応中に副生成物であるメタノール、水が合計130g留出した。
500mlのフラスコに2,2’−アゾビス(イソブチロニトリル)を5g、t−ドデカンチオールを5g、PGMEAを180g仕込んだ。その後、メタクリル酸を30g、ベンジルメタクリレートを35g、トリシクロ[5.2.1.02,6]デカン−8−イルメタクリレートを35g仕込み、室温で攪拌してフラスコ内を窒素置換した後、70℃で5時間加熱攪拌した。次に、得られた溶液にメタクリル酸グリシジルを15g、ジメチルベンジルアミンを1g、p−メトキシフェノールを0.2g添加し、90℃で4時間加熱攪拌し、アクリル樹脂溶液(a)を得た。
乾燥窒素気流下、TrisP−PA(商品名、本州化学工業(株)製)21.23g(0.05mol)と5−ナフトキノンジアジドスルホニル酸クロリド37.62g(0.14mol)を1,4−ジオキサン450gに溶解させ、室温にした。ここに、1,4−ジオキサン50gと混合させたトリエチルアミン15.58g(0.154mol)を系内が35℃以上にならないように滴下した。滴下後30℃で2時間攪拌した。トリエチルアミン塩を濾過し、濾液を水に投入させた。その後、析出した沈殿を濾過で集めた。この沈殿を真空乾燥機で乾燥させ、下記構造のキノンジアジド化合物(a)を得た。
乾燥窒素気流下、TrisP−HAP(商品名、本州化学工業(株)製)15.32g(0.05mol)と5−ナフトキノンジアジドスルホニル酸クロリド26.87g(0.1mol)を1,4−ジオキサン450gに溶解させ、室温にした。ここに、1,4−ジオキサン50gと混合させたトリエチルアミン11.13g(0.11mol)を系内が35℃以上にならないように滴下した。滴下後30℃で2時間攪拌した。トリエチルアミン塩を濾過し、濾液を水に投入させた。その後、析出した沈殿を濾過で集めた。この沈殿を真空乾燥機で乾燥させ、下記構造のキノンジアジド化合物(b)を得た。
合成例1で得られたポリシロキサン溶液(a)22.29g、合成例9で得られたキノンジアジド化合物(a)0.58g、溶剤としてDAA6.10g、GBL0.99gを黄色灯下で混合、攪拌して均一溶液とした後、0.45μmのフィルターで濾過して組成物1を調製した。
ラムダエースSTM−602(商品名、大日本スクリーン製)を用い、屈折率を1.50として測定を行った。
残膜率は以下の式に従って算出した。
残膜率(%)=現像後の未露光部膜厚÷プリベーク後の膜厚×100
(5)感度の算出
露光、現像後、10μmのライン・アンド・スペースパターンを1対1の幅に形成する露光量(以下、これを最適露光量という)を感度とした。
最適露光量における現像後の最小パターン寸法を現像後解像度、キュア後の最小パターン寸法をキュア後解像度とした。
シリコンウェハ上に組成物の硬化膜を形成し、このサンプルを70℃に加熱したアルカリ系剥離液TOK−106(商品名、東京応化工業(株)製)に10分間浸した後、水で5分間リンスした。この処理による膜厚減少量が0.1im以下である場合に耐薬品性が良好、0.05im以下である場合に耐薬品性が特に良好であるとした。
MultiSpec−1500(商品名、(株)島津製作所)を用いて、まずOA−10ガラス板のみを測定し、その紫外可視吸収スペクトルをリファレンスとした。次にOA−10ガラス板上に組成物の硬化膜を形成(パターン露光は行わない)し、このサンプルをシングルビームで測定し、3μmあたりの波長400nmでの光透過率を求め、リファレンスとの差異を硬化膜の光透過率とした。
組成物1と同様に、組成物2〜13を表1に記載の組成にて調製した。なお、シランカップリング剤として用いたKBM303は信越化学工業(株)製の(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である。架橋剤として用いたニカラックMX−270、ニカラックMW−30HM(商品名、三和ケミカル(株)製)は下記に示した構造の化合物である。また、架橋促進剤として用いたWPAG−469(商品名、和光純薬工業(株)製)は4−メチルフェニルジフェニルスルホニウムパーフルオロブタンスルホナート20%PGMEA溶液、増感剤として用いたDPA(商品名、川崎化成工業(株)製)は9,10−ジプロポキシアントラセンである。
Claims (5)
- (a)ポリシロキサン、(b)ナフトキノンジアジド化合物、(c)4級アンモニウム塩、(d)溶剤を含有するポジ型感光性組成物。
- (c)4級アンモニウム塩が、スルホン酸塩および/または硫酸水素塩であることを特徴とする請求項1または2記載のポジ型感光性組成物。
- 請求項1から3のいずれかに記載のポジ型感光性組成物から形成された硬化膜であって、波長400nmにおける膜厚3μmあたりの光透過率が90%以上である硬化膜。
- 請求項4記載の硬化膜を具備する素子。
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WO2015030004A1 (ja) * | 2013-08-29 | 2015-03-05 | 日産化学工業株式会社 | 硬化膜形成組成物、配向材および位相差材 |
JP2018066786A (ja) * | 2016-10-17 | 2018-04-26 | 日立化成デュポンマイクロシステムズ株式会社 | 感光性樹脂組成物、硬化膜、パターン硬化膜の製造方法及び電子部品 |
CN110546566A (zh) * | 2017-04-28 | 2019-12-06 | 默克专利有限公司 | 正型感光性硅氧烷组合物以及使用其而形成的固化膜 |
KR20190137928A (ko) * | 2017-04-28 | 2019-12-11 | 메르크 파텐트 게엠베하 | 포지티브형 감광성 실록산 조성물 및 이를 사용하여 형성된 경화막 |
CN114945867A (zh) * | 2020-01-21 | 2022-08-26 | 东丽株式会社 | 正型感光性树脂组合物、固化膜、层叠体、带导电图案的基板、层叠体的制造方法、触控面板及有机el显示装置 |
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WO2015030004A1 (ja) * | 2013-08-29 | 2015-03-05 | 日産化学工業株式会社 | 硬化膜形成組成物、配向材および位相差材 |
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CN110709773A (zh) * | 2017-04-28 | 2020-01-17 | 默克专利有限公司 | 正型感光性硅氧烷组合物以及使用其而形成的固化膜 |
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CN110709773B (zh) * | 2017-04-28 | 2024-02-09 | 默克专利有限公司 | 正型感光性硅氧烷组合物以及使用其而形成的固化膜 |
CN110546566B (zh) * | 2017-04-28 | 2024-02-09 | 默克专利有限公司 | 正型感光性硅氧烷组合物以及使用其而形成的固化膜 |
CN114945867A (zh) * | 2020-01-21 | 2022-08-26 | 东丽株式会社 | 正型感光性树脂组合物、固化膜、层叠体、带导电图案的基板、层叠体的制造方法、触控面板及有机el显示装置 |
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