WO2012060268A1 - トリアジン環含有重合体およびそれを含む膜形成用組成物 - Google Patents
トリアジン環含有重合体およびそれを含む膜形成用組成物 Download PDFInfo
- Publication number
- WO2012060268A1 WO2012060268A1 PCT/JP2011/074749 JP2011074749W WO2012060268A1 WO 2012060268 A1 WO2012060268 A1 WO 2012060268A1 JP 2011074749 W JP2011074749 W JP 2011074749W WO 2012060268 A1 WO2012060268 A1 WO 2012060268A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- triazine ring
- film
- containing polymer
- polymer
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 98
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title claims abstract description 60
- 239000000203 mixture Substances 0.000 title claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims description 75
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 239000000463 material Substances 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000003282 alkyl amino group Chemical group 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 238000003384 imaging method Methods 0.000 claims description 10
- 125000001769 aryl amino group Chemical group 0.000 claims description 9
- 125000005370 alkoxysilyl group Chemical group 0.000 claims description 7
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 7
- 229910044991 metal oxide Inorganic materials 0.000 claims description 7
- 150000004706 metal oxides Chemical class 0.000 claims description 7
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000001174 sulfone group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 239000004065 semiconductor Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 2
- 230000000295 complement effect Effects 0.000 claims description 2
- -1 2-methyl-cyclopropyl group Chemical group 0.000 description 215
- 239000010408 film Substances 0.000 description 46
- 239000002904 solvent Substances 0.000 description 38
- 238000005259 measurement Methods 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 34
- 238000000034 method Methods 0.000 description 30
- 229920000587 hyperbranched polymer Polymers 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 24
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 16
- 150000004820 halides Chemical class 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 14
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 14
- 239000004793 Polystyrene Substances 0.000 description 13
- 229940018564 m-phenylenediamine Drugs 0.000 description 13
- 229920000647 polyepoxide Polymers 0.000 description 13
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- 229920001187 thermosetting polymer Polymers 0.000 description 13
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 12
- 238000005227 gel permeation chromatography Methods 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
- 229920002223 polystyrene Polymers 0.000 description 12
- 230000004580 weight loss Effects 0.000 description 12
- 238000000576 coating method Methods 0.000 description 11
- 239000003431 cross linking reagent Substances 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- 238000010586 diagram Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000004132 cross linking Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- XPAQFJJCWGSXGJ-UHFFFAOYSA-N 4-amino-n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 XPAQFJJCWGSXGJ-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
- 239000003822 epoxy resin Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000002966 varnish Substances 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 0 *C(C1*)C(*)C(*)=C(*)C1C=C Chemical compound *C(C1*)C(*)C(*)=C(*)C1C=C 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000005401 electroluminescence Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical class C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 238000010304 firing Methods 0.000 description 4
- 230000001771 impaired effect Effects 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 125000003566 oxetanyl group Chemical group 0.000 description 4
- 229920001568 phenolic resin Polymers 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 3
- 238000011088 calibration curve Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000013065 commercial product Substances 0.000 description 3
- 239000000412 dendrimer Substances 0.000 description 3
- 229920000736 dendritic polymer Polymers 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- YZVWKHVRBDQPMQ-UHFFFAOYSA-N 1-aminopyrene Chemical compound C1=C2C(N)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 YZVWKHVRBDQPMQ-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- KUMMBDBTERQYCG-UHFFFAOYSA-N 2,6-bis(hydroxymethyl)-4-methylphenol Chemical compound CC1=CC(CO)=C(O)C(CO)=C1 KUMMBDBTERQYCG-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- PFNHSEQQEPMLNI-UHFFFAOYSA-N 2-methyl-1-pentanol Chemical compound CCCC(C)CO PFNHSEQQEPMLNI-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000004147 Sorbitan trioleate Substances 0.000 description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical class C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 238000004380 ashing Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000006841 cyclic skeleton Chemical group 0.000 description 2
- VEZUQRBDRNJBJY-UHFFFAOYSA-N cyclohexanone oxime Chemical compound ON=C1CCCCC1 VEZUQRBDRNJBJY-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 229920006244 ethylene-ethyl acrylate Polymers 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 229920005669 high impact polystyrene Polymers 0.000 description 2
- 239000004797 high-impact polystyrene Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-methyl-PhOH Natural products CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 2
- 150000007974 melamines Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-methyl phenol Natural products CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920000747 poly(lactic acid) Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 239000004626 polylactic acid Substances 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920001955 polyphenylene ether Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 235000019337 sorbitan trioleate Nutrition 0.000 description 2
- 229960000391 sorbitan trioleate Drugs 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 229940113165 trimethylolpropane Drugs 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 1
- PXJACNDVRNAFHD-UHFFFAOYSA-N (2-methoxyphenyl)methanamine Chemical compound COC1=CC=CC=C1CN PXJACNDVRNAFHD-UHFFFAOYSA-N 0.000 description 1
- RGXUCUWVGKLACF-UHFFFAOYSA-N (3-methylphenyl)methanamine Chemical compound CC1=CC=CC(CN)=C1 RGXUCUWVGKLACF-UHFFFAOYSA-N 0.000 description 1
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 1
- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 description 1
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 description 1
- JHNRZXQVBKRYKN-VQHVLOKHSA-N (ne)-n-(1-phenylethylidene)hydroxylamine Chemical compound O\N=C(/C)C1=CC=CC=C1 JHNRZXQVBKRYKN-VQHVLOKHSA-N 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- JDGFELYPUWNNGR-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropentalene-1,3,4,6-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C2C(C(=O)O)CC(C(O)=O)C21 JDGFELYPUWNNGR-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- SBHHKGFHJWTZJN-UHFFFAOYSA-N 1,3-dimethylcyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1(C)C(C(O)=O)C(C)(C(O)=O)C1C(O)=O SBHHKGFHJWTZJN-UHFFFAOYSA-N 0.000 description 1
- VZXPHDGHQXLXJC-UHFFFAOYSA-N 1,6-diisocyanato-5,6-dimethylheptane Chemical compound O=C=NC(C)(C)C(C)CCCCN=C=O VZXPHDGHQXLXJC-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 1
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- 125000006433 1-ethyl cyclopropyl group Chemical group [H]C([H])([H])C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- CSZZMFWKAQEMPB-UHFFFAOYSA-N 1-methoxybutan-2-ol Chemical compound CCC(O)COC CSZZMFWKAQEMPB-UHFFFAOYSA-N 0.000 description 1
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
- 125000006439 1-n-propyl cyclopropyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- PZVPOYBHOPRJNP-UHFFFAOYSA-N 2,2-dimethylbutan-1-amine Chemical compound CCC(C)(C)CN PZVPOYBHOPRJNP-UHFFFAOYSA-N 0.000 description 1
- XDIAMRVROCPPBK-UHFFFAOYSA-N 2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN XDIAMRVROCPPBK-UHFFFAOYSA-N 0.000 description 1
- NEBBLNDVSSWJLL-UHFFFAOYSA-N 2,3-bis(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OCC(OC(=O)C(C)=C)COC(=O)C(C)=C NEBBLNDVSSWJLL-UHFFFAOYSA-N 0.000 description 1
- PUGOMSLRUSTQGV-UHFFFAOYSA-N 2,3-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical class C=CC(=O)OCC(OC(=O)C=C)COC(=O)C=C PUGOMSLRUSTQGV-UHFFFAOYSA-N 0.000 description 1
- GBMSZXWHMSSBGP-UHFFFAOYSA-N 2,3-dimethylbutan-1-amine Chemical compound CC(C)C(C)CN GBMSZXWHMSSBGP-UHFFFAOYSA-N 0.000 description 1
- YQNVPNRHJFZONU-UHFFFAOYSA-N 2,3-dimethylbutan-2-amine Chemical compound CC(C)C(C)(C)N YQNVPNRHJFZONU-UHFFFAOYSA-N 0.000 description 1
- NSBGRQGYTRBWNG-UHFFFAOYSA-N 2,4-bis(hydroxymethyl)-6-methylphenol Chemical compound CC1=CC(CO)=CC(CO)=C1O NSBGRQGYTRBWNG-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- DVPBWLLOGOINDW-UHFFFAOYSA-N 2-(5-bromo-1h-indol-3-yl)acetamide Chemical compound C1=C(Br)C=C2C(CC(=O)N)=CNC2=C1 DVPBWLLOGOINDW-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- SEFYJVFBMNOLBK-UHFFFAOYSA-N 2-[2-[2-(oxiran-2-ylmethoxy)ethoxy]ethoxymethyl]oxirane Chemical compound C1OC1COCCOCCOCC1CO1 SEFYJVFBMNOLBK-UHFFFAOYSA-N 0.000 description 1
- NREFJJBCYMZUEK-UHFFFAOYSA-N 2-[2-[4-[2-[4-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]phenyl]propan-2-yl]phenoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound C1=CC(OCCOCCOC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCCOCCOC(=O)C(C)=C)C=C1 NREFJJBCYMZUEK-UHFFFAOYSA-N 0.000 description 1
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
- PPEASEWKOGNDKZ-UHFFFAOYSA-N 2-[[2,6-bis(oxiran-2-ylmethyl)phenoxy]methyl]oxirane Chemical compound C1OC1COC(C(=CC=C1)CC2OC2)=C1CC1CO1 PPEASEWKOGNDKZ-UHFFFAOYSA-N 0.000 description 1
- BXVXPASMKWYBFD-UHFFFAOYSA-N 2-[[2-hydroxy-3-(hydroxymethyl)-5-methylphenyl]methyl]-6-(hydroxymethyl)-4-methylphenol Chemical compound CC1=CC(CO)=C(O)C(CC=2C(=C(CO)C=C(C)C=2)O)=C1 BXVXPASMKWYBFD-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- WZKPOAWBXHEIKH-UHFFFAOYSA-N 2-[[4-[1,3-bis[4-(oxiran-2-ylmethoxy)phenyl]propyl]phenoxy]methyl]oxirane Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C=1C=CC(OCC2OC2)=CC=1)CCC(C=C1)=CC=C1OCC1CO1 WZKPOAWBXHEIKH-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- BGVCWPVMJIEXBL-UHFFFAOYSA-N 2-ethoxyhexan-1-ol Chemical compound CCCCC(CO)OCC BGVCWPVMJIEXBL-UHFFFAOYSA-N 0.000 description 1
- JMWGZSWSTCGVLX-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methylprop-2-enoic acid Chemical class CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CCC(CO)(CO)CO JMWGZSWSTCGVLX-UHFFFAOYSA-N 0.000 description 1
- MGWAGIQQTULHGU-UHFFFAOYSA-N 2-ethylbutan-1-amine Chemical compound CCC(CC)CN MGWAGIQQTULHGU-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- VJROPLWGFCORRM-UHFFFAOYSA-N 2-methylbutan-1-amine Chemical compound CCC(C)CN VJROPLWGFCORRM-UHFFFAOYSA-N 0.000 description 1
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 1
- WNDXRJBYZOSNQO-UHFFFAOYSA-N 2-methylpentan-1-amine Chemical compound CCCC(C)CN WNDXRJBYZOSNQO-UHFFFAOYSA-N 0.000 description 1
- KPNJYXKRHWAPHP-UHFFFAOYSA-N 2-methylpentan-2-amine Chemical compound CCCC(C)(C)N KPNJYXKRHWAPHP-UHFFFAOYSA-N 0.000 description 1
- JYNQKCFJPQEXSL-UHFFFAOYSA-N 2-methylpentan-3-amine Chemical compound CCC(N)C(C)C JYNQKCFJPQEXSL-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- NWIIFBPIDORBCY-UHFFFAOYSA-N 2-methylprop-2-enoic acid;propane-1,2,3-triol;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(=C)C(O)=O.OCC(O)CO NWIIFBPIDORBCY-UHFFFAOYSA-N 0.000 description 1
- BNCADMBVWNPPIZ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n,6-n,6-n-hexakis(methoxymethyl)-1,3,5-triazine-2,4,6-triamine Chemical compound COCN(COC)C1=NC(N(COC)COC)=NC(N(COC)COC)=N1 BNCADMBVWNPPIZ-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- HCGFUIQPSOCUHI-UHFFFAOYSA-N 2-propan-2-yloxyethanol Chemical compound CC(C)OCCO HCGFUIQPSOCUHI-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- GPWHFPWZAPOYNO-UHFFFAOYSA-N 3,3-dimethylbutan-1-amine Chemical compound CC(C)(C)CCN GPWHFPWZAPOYNO-UHFFFAOYSA-N 0.000 description 1
- DXSUORGKJZADET-UHFFFAOYSA-N 3,3-dimethylbutan-2-amine Chemical compound CC(N)C(C)(C)C DXSUORGKJZADET-UHFFFAOYSA-N 0.000 description 1
- WONYMNWUJVKVII-UHFFFAOYSA-N 3,5-diiodothyropropionic acid Chemical compound IC1=CC(CCC(=O)O)=CC(I)=C1OC1=CC=C(O)C=C1 WONYMNWUJVKVII-UHFFFAOYSA-N 0.000 description 1
- SDXAWLJRERMRKF-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazole Chemical compound CC=1C=C(C)NN=1 SDXAWLJRERMRKF-UHFFFAOYSA-N 0.000 description 1
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
- BUZICZZQJDLXJN-UHFFFAOYSA-N 3-azaniumyl-4-hydroxybutanoate Chemical compound OCC(N)CC(O)=O BUZICZZQJDLXJN-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 1
- JOZZAIIGWFLONA-UHFFFAOYSA-N 3-methylbutan-2-amine Chemical compound CC(C)C(C)N JOZZAIIGWFLONA-UHFFFAOYSA-N 0.000 description 1
- JLAUIBFZZUVOBB-UHFFFAOYSA-N 3-methylpentan-1-amine Chemical compound CCC(C)CCN JLAUIBFZZUVOBB-UHFFFAOYSA-N 0.000 description 1
- VQMPTVQCADWACQ-UHFFFAOYSA-N 3-methylpentan-3-amine Chemical compound CCC(C)(N)CC VQMPTVQCADWACQ-UHFFFAOYSA-N 0.000 description 1
- OAJCSERLBQROJC-UHFFFAOYSA-N 3-octyloxolane-2,5-dione Chemical compound CCCCCCCCC1CC(=O)OC1=O OAJCSERLBQROJC-UHFFFAOYSA-N 0.000 description 1
- ATGIXVUZFPZOHP-UHFFFAOYSA-N 4-(4-phenylphenyl)aniline Chemical group C1=CC(N)=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ATGIXVUZFPZOHP-UHFFFAOYSA-N 0.000 description 1
- VNWVYPAQLKRTSC-UHFFFAOYSA-N 4-[(4-hydroxy-2,5-dimethylphenyl)methyl]benzaldehyde Chemical compound OC1=CC(=C(C=C1C)CC1=CC=C(C=C1)C=O)C VNWVYPAQLKRTSC-UHFFFAOYSA-N 0.000 description 1
- APXJLYIVOFARRM-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(C(O)=O)C(C(O)=O)=C1 APXJLYIVOFARRM-UHFFFAOYSA-N 0.000 description 1
- ZRIRUWWYQXWRNY-UHFFFAOYSA-N 4-[2-[4-hydroxy-3,5-bis(hydroxymethyl)phenyl]propan-2-yl]-2,6-bis(hydroxymethyl)phenol Chemical compound C=1C(CO)=C(O)C(CO)=CC=1C(C)(C)C1=CC(CO)=C(O)C(CO)=C1 ZRIRUWWYQXWRNY-UHFFFAOYSA-N 0.000 description 1
- FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 description 1
- DOMBBFBDIIXIKP-UHFFFAOYSA-N 4-[[4-hydroxy-3-(hydroxymethyl)-5-methylphenyl]methyl]-2-(hydroxymethyl)-6-methylphenol Chemical compound OCC1=C(O)C(C)=CC(CC=2C=C(CO)C(O)=C(C)C=2)=C1 DOMBBFBDIIXIKP-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- QVIAMKXOQGCYCV-UHFFFAOYSA-N 4-methylpentan-1-amine Chemical compound CC(C)CCCN QVIAMKXOQGCYCV-UHFFFAOYSA-N 0.000 description 1
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 1
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 1
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 1
- XKVUYEYANWFIJX-UHFFFAOYSA-N 5-methyl-1h-pyrazole Chemical compound CC1=CC=NN1 XKVUYEYANWFIJX-UHFFFAOYSA-N 0.000 description 1
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CFRFHWQYWJMEJN-UHFFFAOYSA-N 9h-fluoren-2-amine Chemical compound C1=CC=C2C3=CC=C(N)C=C3CC2=C1 CFRFHWQYWJMEJN-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229920003319 Araldite® Polymers 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- NDZZPFWJQPPJCN-UHFFFAOYSA-N C(C)(=O)N1CCCC1.CN1C(CCCCC1)=O Chemical compound C(C)(=O)N1CCCC1.CN1C(CCCCC1)=O NDZZPFWJQPPJCN-UHFFFAOYSA-N 0.000 description 1
- OJZVOIIFGPOCIT-UHFFFAOYSA-N CC(CC(C)C)N.CC(C(CC)C)N Chemical compound CC(CC(C)C)N.CC(C(CC)C)N OJZVOIIFGPOCIT-UHFFFAOYSA-N 0.000 description 1
- BGQAZAHWMRSYGG-UHFFFAOYSA-N CCCCO.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O Chemical compound CCCCO.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O BGQAZAHWMRSYGG-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 229920013683 Celanese Polymers 0.000 description 1
- 229920002284 Cellulose triacetate Polymers 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- 229920003270 Cymel® Polymers 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 239000004368 Modified starch Substances 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- 101100389975 Mus musculus Ezhip gene Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- BDNSYCVENKDFGW-UHFFFAOYSA-N OC1=CC(=C(C=C1C)C(C=O)C1=C(C=C(C(=C1)C)O)C)C.C(=O)C=1C=C(C=CC1O)CC1=CC(=C(C=C1)O)C=O Chemical compound OC1=CC(=C(C=C1C)C(C=O)C1=C(C=C(C(=C1)C)O)C)C.C(=O)C=1C=C(C=CC1O)CC1=CC(=C(C=C1)O)C=O BDNSYCVENKDFGW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000233805 Phoenix Species 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 229920000954 Polyglycolide Polymers 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- NNLVGZFZQQXQNW-ADJNRHBOSA-N [(2r,3r,4s,5r,6s)-4,5-diacetyloxy-3-[(2s,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6s)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound O([C@@H]1O[C@@H]([C@H]([C@H](OC(C)=O)[C@H]1OC(C)=O)O[C@H]1[C@@H]([C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1)OC(C)=O)COC(=O)C)[C@@H]1[C@@H](COC(C)=O)O[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O NNLVGZFZQQXQNW-ADJNRHBOSA-N 0.000 description 1
- ULQMPOIOSDXIGC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)COC(=O)C(C)=C ULQMPOIOSDXIGC-UHFFFAOYSA-N 0.000 description 1
- JUDXBRVLWDGRBC-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(COC(=O)C(C)=C)COC(=O)C(C)=C JUDXBRVLWDGRBC-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- KGBBDBRJXGILTQ-UHFFFAOYSA-N [3-(2-methylprop-2-enoyloxy)-2,2-bis(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical class CC(=C)C(=O)OCC(COC(=O)C(C)=C)(COC(=O)C(C)=C)COC(=O)C(C)=C KGBBDBRJXGILTQ-UHFFFAOYSA-N 0.000 description 1
- KNSXNCFKSZZHEA-UHFFFAOYSA-N [3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical class C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C KNSXNCFKSZZHEA-UHFFFAOYSA-N 0.000 description 1
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical class C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 1
- VEBCLRKUSAGCDF-UHFFFAOYSA-N ac1mi23b Chemical compound C1C2C3C(COC(=O)C=C)CCC3C1C(COC(=O)C=C)C2 VEBCLRKUSAGCDF-UHFFFAOYSA-N 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229920001893 acrylonitrile styrene Polymers 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000007754 air knife coating Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- YUENFNPLGJCNRB-UHFFFAOYSA-N anthracen-1-amine Chemical compound C1=CC=C2C=C3C(N)=CC=CC3=CC2=C1 YUENFNPLGJCNRB-UHFFFAOYSA-N 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 125000000732 arylene group Chemical group 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 1
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
- 125000006616 biphenylamine group Chemical group 0.000 description 1
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical class C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- MBZQWRBRCHBZDH-UHFFFAOYSA-N butane-1,2,3,4-tetracarboxylic acid 5-(2,5-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound OC(=O)CC(C(CC(O)=O)C(O)=O)C(O)=O.CC1=CC(CC2C1C(=O)OC2=O)C1CC(=O)OC1=O MBZQWRBRCHBZDH-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- FFQYMTMKMLRXLJ-UHFFFAOYSA-N cyclohexanol;phenol Chemical compound OC1CCCCC1.OC1=CC=CC=C1 FFQYMTMKMLRXLJ-UHFFFAOYSA-N 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical group C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- WCTQEHGXBKFLKG-UHFFFAOYSA-N ethyl 4-(aminomethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(CN)C=C1 WCTQEHGXBKFLKG-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000005042 ethylene-ethyl acrylate Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000003779 heat-resistant material Substances 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- WGBBUURBHXLGFM-UHFFFAOYSA-N hexan-2-amine Chemical compound CCCCC(C)N WGBBUURBHXLGFM-UHFFFAOYSA-N 0.000 description 1
- HQLZFBUAULNEGP-UHFFFAOYSA-N hexan-3-amine Chemical compound CCCC(N)CC HQLZFBUAULNEGP-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002605 large molecules Chemical group 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 150000004988 m-phenylenediamines Chemical class 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- AQBJGAUQEJFPKZ-UHFFFAOYSA-N methyl 4-(aminomethyl)benzoate Chemical compound COC(=O)C1=CC=C(CN)C=C1 AQBJGAUQEJFPKZ-UHFFFAOYSA-N 0.000 description 1
- LZXXNPOYQCLXRS-UHFFFAOYSA-N methyl 4-aminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1 LZXXNPOYQCLXRS-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- GXMIHVHJTLPVKL-UHFFFAOYSA-N n,n,2-trimethylpropanamide Chemical compound CC(C)C(=O)N(C)C GXMIHVHJTLPVKL-UHFFFAOYSA-N 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- ZCOGQSHZVSZAHH-UHFFFAOYSA-N n,n-dimethylaziridine-1-carboxamide Chemical compound CN(C)C(=O)N1CC1 ZCOGQSHZVSZAHH-UHFFFAOYSA-N 0.000 description 1
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 description 1
- ZKALVNREMFLWAN-UHFFFAOYSA-N n-(4-methylpentan-2-ylidene)hydroxylamine Chemical compound CC(C)CC(C)=NO ZKALVNREMFLWAN-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PZYDAVFRVJXFHS-UHFFFAOYSA-N n-cyclohexyl-2-pyrrolidone Chemical compound O=C1CCCN1C1CCCCC1 PZYDAVFRVJXFHS-UHFFFAOYSA-N 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- ISRXMEYARGEVIU-UHFFFAOYSA-N n-methyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C)C(C)C ISRXMEYARGEVIU-UHFFFAOYSA-N 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- IGEIPFLJVCPEKU-UHFFFAOYSA-N pentan-2-amine Chemical compound CCCC(C)N IGEIPFLJVCPEKU-UHFFFAOYSA-N 0.000 description 1
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000412 polyarylene Polymers 0.000 description 1
- 239000004631 polybutylene succinate Substances 0.000 description 1
- 229920002961 polybutylene succinate Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000223 polyglycerol Polymers 0.000 description 1
- 239000004633 polyglycolic acid Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- MFUFBSLEAGDECJ-UHFFFAOYSA-N pyren-2-ylamine Natural products C1=CC=C2C=CC3=CC(N)=CC4=CC=C1C2=C43 MFUFBSLEAGDECJ-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 150000003553 thiiranes Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
- C08G73/0638—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with at least three nitrogen atoms in the ring
- C08G73/0644—Poly(1,3,5)triazines
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0273—Polyamines containing heterocyclic moieties in the main chain
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/028—Polyamidoamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D177/00—Coating compositions based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Coating compositions based on derivatives of such polymers
- C09D177/10—Polyamides derived from aromatically bound amino and carboxyl groups of amino carboxylic acids or of polyamines and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D179/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09D161/00 - C09D177/00
- C09D179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14601—Structural or functional details thereof
- H01L27/1462—Coatings
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14601—Structural or functional details thereof
- H01L27/1462—Coatings
- H01L27/14621—Colour filter arrangements
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/14643—Photodiode arrays; MOS imagers
- H01L27/14645—Colour imagers
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/148—Charge coupled imagers
- H01L27/14806—Structural or functional details thereof
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
- H01L27/148—Charge coupled imagers
- H01L27/14868—CCD or CID colour imagers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/60—OLEDs integrated with inorganic light-sensitive elements, e.g. with inorganic solar cells or inorganic photodiodes
- H10K59/65—OLEDs integrated with inorganic image sensors
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F2202/00—Materials and properties
- G02F2202/02—Materials and properties organic material
- G02F2202/022—Materials and properties organic material polymeric
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F2202/00—Materials and properties
- G02F2202/40—Materials having a particular birefringence, retardation
Definitions
- the present invention relates to a triazine ring-containing polymer and a film-forming composition containing the same.
- Patent Document 1 a technique for increasing the refractive index using a hybrid material obtained by mixing a siloxane polymer and a fine particle dispersion material in which zirconia or titania is dispersed has been reported.
- Patent Document 2 a method of introducing a condensed cyclic skeleton having a high refractive index into a part of the siloxane polymer has been reported.
- melamine resin is well known as a triazine resin, but its decomposition temperature is much lower than that of heat-resistant materials such as graphite.
- aromatic polyimides and aromatic polyamides have been mainly used as heat-resistant organic materials composed of carbon and nitrogen. However, these materials have a linear structure, so that the heat-resistant temperature is not so high.
- a triazine-based condensation material has also been reported as a nitrogen-containing polymer material having heat resistance (Patent Document 4).
- a polymer compound into which an aromatic ring or a triazine ring is introduced generally lacks solubility in a solvent, and therefore is insoluble in a resist solvent, which is a safety solvent, while having high solubility.
- the materials shown are generally less transparent.
- a material using an inorganic metal oxide has a trade-off relationship between a refractive index and transparency, and thus it is difficult to improve transparency while maintaining a high refractive index.
- this material contains fine particles with different properties, when a dry process such as etching or ashing is performed, the etch rate becomes unstable and it is difficult to obtain a film with a uniform film thickness. There is also a problem that the process margin becomes narrow.
- hyperbranched polymers are roughly classified into hyperbranched polymers and dendrimers.
- the hyperbranched polymer is, for example, an ABx type polyfunctional monomer (where A and B are functional groups that react with each other, and the number X of B is 2 or more) that has an irregular branched structure obtained by polymerizing. It is a branched polymer.
- a dendrimer is a highly branched polymer having a regular branched structure. Hyperbranched polymers are characterized by being easier to synthesize than dendrimers and easier to synthesize high molecular weight polymers.
- a hyperbranched polymer having a triazine ring has been reported as a flame retardant application (Non-patent Document 1).
- the present invention has been made in view of the above circumstances, and a triazine that can achieve high heat resistance, high transparency, high refractive index, high solubility, and low volume shrinkage by itself without adding a metal oxide.
- An object of the present invention is to provide a ring-containing polymer and a film-forming composition containing the same.
- the present inventors have found that a hyperbranched polymer including a repeating unit having a triazine ring and an aromatic ring has a refractive index exceeding 1.7, and the polymer alone has high heat resistance, high transparency, high refractive index, and high solubility. It has already been found that it can achieve low volume shrinkage and is suitable as a film-forming composition for producing electronic devices (PCT / JP2010 / 057761). Based on this knowledge, the present inventors have conducted further studies. As a result, the present inventors have found a copolymer-type hyperbranched polymer excellent in refractive index, heat resistance, and solubility in various organic solvents, and completed the present invention.
- a triazine ring-containing polymer comprising a repeating unit structure represented by the following formula (1): ⁇ Wherein R, R ′, R ′′ and R ′ ′′ each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or an aralkyl group, and Ar 1 and Ar 2 are different from each other.
- R 132 to R 135 are each independently a hydrogen atom, a halogen atom, a carboxyl group, a sulfone group, an alkyl group which may have a branched structure having 1 to 10 carbon atoms, or 1 carbon atom
- Y 1 and Y 2 each independently represent an alkylene group that may have a single bond or a branched structure of 1 to 10 carbon atoms.
- One triazine ring-containing polymer, wherein the repeating unit structure comprises formula (25); 6).
- One triazine ring-containing polymer, wherein the repeating unit structure comprises formula (26); 7.
- One triazine ring-containing polymer, wherein the repeating unit structure comprises formula (27); 8).
- At least one terminal is an alkyl group, aralkyl group, aryl group, alkylamino group, alkoxysilyl group-containing alkylamino group, aralkylamino group, arylamino group, alkoxy group, aralkyloxy group, aryloxy group, or ester group. Any of the capped triazine ring-containing polymers of 1 to 7, 9.
- triazine ring end Having at least one triazine ring end, and the triazine ring end is an alkyl group, an aralkyl group, an aryl group, an alkylamino group, an alkoxysilyl group-containing alkylamino group, an aralkylamino group, an arylamino group, an alkoxy group, an aralkyloxy group 8 triazine ring-containing polymers capped with groups, aryloxy groups, or ester groups, 10.
- a film-forming composition comprising any one of the triazine ring-containing polymers of 1 to 9, 11.
- a film obtained from 10 film-forming compositions; 12 A film comprising the triazine ring-containing polymer of any one of 1 to 9, 13.
- An electronic device comprising a substrate and 11 or 12 films formed on the substrate; 14 An optical member comprising a base material and 11 or 12 films formed on the base material; 15. A solid-state imaging device comprising a charge-coupled device or a complementary metal oxide semiconductor, comprising at least one layer of 11 or 12; 16. A solid-state imaging device comprising 11 or 12 films as a planarizing layer on a color filter; 17. A lens material, a planarizing material or an embedding material for a solid-state imaging device, comprising 10 film forming compositions.
- the present invention it is possible to provide a triazine ring-containing polymer that can achieve high heat resistance, high transparency, high refractive index, high solubility, and low volume shrinkage independently without using a metal oxide.
- a polymer skeleton of the present invention high heat resistance and high transparency can be maintained even when 1) a secondary amine is used as a polymer spacer and 2) a primary amine is substituted at the terminal.
- the hyperbranched polymer of the present invention exhibits a high refractive index because the tribranched structure and the aryl (Ar) portion are closely gathered to increase the electron density. It is done.
- R, R ′, R ′′, and R ′ ′′ is a hydrogen atom
- a hyperbranched structure allows the nitrogen atom on the triazine ring and the hydrogen atom at the amine site to hydrogen bond. It is considered that the triazine ring and the aryl (Ar) portion are more closely gathered to increase the electron density.
- it is a high molecular weight compound, it is excellent in solubility in various organic solvents, and also has excellent handling properties because it has a low viscosity when dissolved in a solvent.
- the triazine ring-containing polymer of the present invention can be used as a high heat resistant insulating material.
- a film prepared using the triazine ring-containing polymer of the present invention having the above-described characteristics is a liquid crystal display, an organic electroluminescence (EL) display, an optical semiconductor (LED) element, a solid-state imaging element, an organic thin film solar cell, It can be suitably used as a member for producing electronic devices such as dye-sensitized solar cells and organic thin film transistors (TFTs).
- a buried film and a planarizing film on a photodiode, a planarizing film before and after a color filter, a microlens, and a planarizing film and a conformal film on a microlens which are members of a solid-state imaging device that requires a high refractive index. Can be suitably used.
- FIG. 1 is a diagram showing a 1 H-NMR spectrum of a polymer compound [4] obtained in Example 1.
- FIG. FIG. 6 is a diagram showing a TG-DTA measurement result in Example 2.
- 4 is a diagram showing a 1 H-NMR spectrum of a polymer compound [4] obtained in Example 4.
- FIG. FIG. 10 is a diagram showing a TG-DTA measurement result in Example 5.
- 6 is a diagram showing a 1 H-NMR spectrum of a polymer compound [4] obtained in Example 7.
- FIG. 10 is a diagram showing a TG-DTA measurement result in Example 8.
- 1 is a diagram showing a 1 H-NMR spectrum of a polymer compound [4] obtained in Example 10.
- FIG. 10 is a view showing a TG-DTA measurement result in Example 11.
- 1 is a diagram showing a 1 H-NMR spectrum of a polymer compound [6] obtained in Example 17.
- FIG. 10 is a view showing a TG-DTA measurement result in Example 18;
- 2 is a diagram showing a 1 H-NMR spectrum of a polymer compound [7] obtained in Example 20.
- FIG. FIG. 10 is a view showing a TG-DTA measurement result in Example 21.
- 2 is a diagram showing a 1 H-NMR spectrum of a polymer compound [6] obtained in Example 22.
- FIG. FIG. 10 is a view showing a TG-DTA measurement result in Example 24.
- the triazine ring-containing polymer according to the present invention includes a repeating unit structure represented by the following formula (1).
- R, R ′, R ′′, and R ′ ′′ each independently represent a hydrogen atom, an alkyl group, an alkoxy group, an aryl group, or an aralkyl group.
- the number of carbon atoms of the alkyl group is not particularly limited, but is preferably 1 to 20, and more preferably 1 to 10 carbon atoms in view of further improving the heat resistance of the polymer. Is even more preferable.
- the structure may be any of a chain, a branch, and a ring.
- alkyl group examples include methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, cyclobutyl group, 1-methyl group.
- -Cyclopropyl group 2-methyl-cyclopropyl group, n-pentyl group, 1-methyl-n-butyl group, 2-methyl-n-butyl group, 3-methyl-n-butyl group, 1,1-dimethyl -N-propyl group, 1,2-dimethyl-n-propyl group, 2,2-dimethyl-n-propyl group, 1-ethyl-n-propyl group, cyclopentyl group, 1-methyl-cyclobutyl group, 2-methyl -Cyclobutyl, 3-methyl-cyclobutyl, 1,2-dimethyl-cyclopropyl, 2,3-dimethyl-cyclopropyl, 1-ethyl-cyclopropyl, 2-ethyl Ru-cyclopropyl group, n-hexyl group, 1-methyl-n-pentyl group, 2-methyl-n-pentyl group, 3-methyl-n-pentyl group, 4-methyl-n-pentyl group,
- the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20, and more preferably 1 to 10 carbon atoms, more preferably 1 to 3 carbon atoms in view of further improving the heat resistance of the polymer. preferable.
- the structure of the alkyl moiety may be any of a chain, a branch, and a ring.
- alkoxy group examples include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, s-butoxy group, t-butoxy group, n-pentoxy group, 1-methyl- n-butoxy group, 2-methyl-n-butoxy group, 3-methyl-n-butoxy group, 1,1-dimethyl-n-propoxy group, 1,2-dimethyl-n-propoxy group, 2,2-dimethyl -N-propoxy group, 1-ethyl-n-propoxy group, n-hexyloxy group, 1-methyl-n-pentyloxy group, 2-methyl-n-pentyloxy group, 3-methyl-n-pentyloxy group 4-methyl-n-pentyloxy group, 1,1-dimethyl-n-butoxy group, 1,2-dimethyl-n-butoxy group, 1,3-dimethyl-n-butoxy group, 2,2-dimethyl Ru-n-butoxy group, 2, 2,2-
- the number of carbon atoms of the aryl group is not particularly limited, but is preferably 6 to 40. In view of further improving the heat resistance of the polymer, 6 to 16 carbon atoms are more preferable, and 6 to 13 are even more preferable. preferable.
- Specific examples of the aryl group include phenyl group, o-chlorophenyl group, m-chlorophenyl group, p-chlorophenyl group, o-fluorophenyl group, p-fluorophenyl group, o-methoxyphenyl group, p-methoxy group.
- the number of carbon atoms of the aralkyl group is not particularly limited, but preferably 7 to 20 carbon atoms, and the alkyl portion may be linear, branched or cyclic. Specific examples thereof include benzyl group, p-methylphenylmethyl group, m-methylphenylmethyl group, o-ethylphenylmethyl group, m-ethylphenylmethyl group, p-ethylphenylmethyl group, 2-propylphenylmethyl group. 4-isopropylphenylmethyl group, 4-isobutylphenylmethyl group, ⁇ -naphthylmethyl group and the like.
- Ar 1 and Ar 2 represent at least one selected from the group represented by formulas (2) to (18), which are different from each other, and combinations thereof are particularly those represented by formulas (5) to (18).
- the two types shown are preferable, and the two types selected from the group shown by the formulas (5) to (12) and (14) to (18) are more preferable, and the formulas (7), (11), (12), ( Two types selected from the group represented by 14) and (15) are even more preferred.
- R 1 to R 128 are each independently a hydrogen atom, a halogen atom, a carboxyl group, a sulfone group, an alkyl group which may have a branched structure having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 carbon atoms.
- X 1 and X 2 each independently represent a single bond, an alkylene group which may have a branched structure having 1 to 10 carbon atoms, or a group represented by the formula (19).
- R 132 to R 135 are each independently a hydrogen atom, a halogen atom, a carboxyl group, a sulfone group, an alkyl group that may have a branched structure having 1 to 10 carbon atoms, or an alkyl group having 1 to 10 carbon atoms.
- An alkoxy group which may have a branched structure is represented, and Y 1 and Y 2 each independently represent an alkylene group which may have a single bond or a branched structure having 1 to 10 carbon atoms. Examples of the halogen atom, alkyl group and alkoxy group are the same as those described above.
- alkylene group that may have a branched structure having 1 to 10 carbon atoms include a methylene group, an ethylene group, a propylene group, a trimethylene group, a tetramethylene group, and a pentamethylene group.
- aryl group represented by the above formulas (2) to (18) include those represented by the following formula, but are not limited thereto.
- an aryl group represented by the following formula is more preferable because a polymer having a higher refractive index can be obtained.
- the aryl portion (Ar 1 and / or Ar 2 portion, the same shall apply hereinafter) has a rigid structure having a cyclic skeleton such as a fluorene skeleton or a carbazole skeleton, while the aryl portion is dense. This is preferable because the electron density is improved and the electron density is improved, and a simple benzene ring is also a small structure. Therefore, the aryl portion is easily concentrated closely and the electron density is improved.
- a carbonyl-containing group or a functional group such as an amine having a high hydrogen bonding ability may be a hydrogen atom (R, R ′, R ′′ and / or R) at an amine site.
- R, R ′, R ′′ and / or R hydrogen atom
- a hydrogen bond is formed, and the aryl portion is more likely to gather more closely, which is preferable because the electron density is improved.
- an aryl group represented by the following formula is preferable.
- an aryl group represented by the following formula is more preferable.
- the aryl group is preferably a group derived from an m-phenylenediamine derivative.
- suitable combinations of Ar 1 and Ar 2 in the present invention include two types selected from the following formulas (20) to (24) It is done.
- R 32 to R 37 , R 69 to R 80 , R 89 to R 104 , R 129 , R 130 and R 132 to R 135 have the same meaning as described above, but all are preferably hydrogen atoms.
- Suitable repeating unit structures in the present invention include, but are not limited to, those represented by the following formulas (25) to (27).
- the weight average molecular weight of the triazine ring-containing hyperbranched polymer of the present invention is not particularly limited, but is preferably 500 to 500,000, more preferably 500 to 100,000, and further improves heat resistance and shrinkage. 2,000 or more is preferable from the viewpoint of lowering the rate, 50,000 or less is preferable, and 30,000 or less is more preferable, from the viewpoint of further increasing the solubility and lowering the viscosity of the obtained solution. Is more preferable.
- the weight average molecular weight in this invention is an average molecular weight obtained by standard polystyrene conversion by gel permeation chromatography (henceforth GPC) analysis.
- the copolymer type triazine ring-containing polymer of the present invention can be obtained by reacting cyanuric halide with at least two kinds of diaminoaryl compounds.
- a repeating structure ( The hyperbranched polymer having 25 ′) can be obtained by reacting cyanuric halide (28), bisaminophenylfluorene compound (29) and m-phenylenediamine compound (30) in a suitable organic solvent.
- the hyperbranched polymer having a repeating structure (25 ′) is obtained by using an equivalent amount of cyanuric halide (28) and bisaminophenylfluorene compound (29) in an appropriate organic solvent.
- the hyperbranched polymer of the present invention can be produced inexpensively, easily and safely. Since this production method is significantly shorter than the reaction time for synthesizing a general polymer, it is a production method suitable for environmental considerations in recent years and can reduce CO 2 emissions. Moreover, stable production is possible even if the production scale is greatly increased, and the stable supply system at the industrialization level is not impaired.
- the amount of each raw material charged is arbitrary as long as the desired polymer is obtained, but the m-phenylenediamine compound (30) and the cyanuric halide (28) are equivalent to 1 equivalent.
- the total amount of the bisaminophenyl fluorene compound (29) is preferably 0.01 to 10 equivalents, but the m-phenylenediamine compound (30) and the bisaminophenyl fluorene compound (29) with respect to 2 equivalents of cyanuric halide (28). It is preferable to avoid using 3 equivalents as the total amount. By shifting the equivalent of the functional group, formation of a gelled product can be prevented.
- m-phenylenediamine compound (30) and bisaminophenylfluorene compound (The total amount of 29) is preferably used in an amount of less than 3 equivalents.
- halogens are used with respect to 3 equivalents in total of m-phenylenediamine compound (30) and bisaminophenylfluorene compound (29).
- Cyanuric (28) is preferably used in an amount of less than 2 equivalents.
- the molecular weight of the hyperbranched polymer (hyperbranched polymer) obtained by appropriately adjusting the amounts of the m-phenylenediamine compound (30), the bisaminophenylfluorene compound (29) and the cyanuric halide (28). can be adjusted easily.
- the amount of each raw material charged is arbitrary as long as the desired hyperbranched polymer is obtained.
- the diamino compound (29), (30) 0.01 to 10 equivalents are preferred respectively.
- organic solvent various solvents usually used in this kind of reaction can be used, for example, tetrahydrofuran, dioxane, dimethyl sulfoxide; N, N-dimethylformamide, N-methyl-2-pyrrolidone, tetramethylurea.
- N, N-dimethylformamide, dimethyl sulfoxide, N-methyl-2-pyrrolidone, N, N-dimethylacetamide, and mixed solvents thereof are preferable, and N, N-dimethylacetamide, N-methyl-2-pyrrolidone are particularly preferable. Is preferred.
- the reaction temperature is appropriately set within the range from the melting point of the solvent used to the boiling point of the solvent. In particular, it is preferably about 0 to 150 ° C, more preferably 60 to 100 ° C. Particularly in the reaction of Scheme 1, the reaction temperature is preferably 60 to 150 ° C., preferably 80 to 150 ° C., and preferably 80 to 120 ° C. from the viewpoint of suppressing linearity and increasing the degree of branching.
- the reaction temperature may be appropriately set in the range from the melting point of the solvent to be used to the boiling point of the solvent.
- About -50 ° C is preferable, about -20 to 50 ° C is more preferable, about -10 to 50 ° C is further preferable, and -10 to 10 ° C is further preferable.
- a two-step process comprising a first step of reacting at ⁇ 50 to 50 ° C. and a second step of reacting at 60 to 150 ° C. following this step is performed. It is preferable to adopt.
- either the component previously dissolved in the solvent or the component added later may be either, but the diamino compounds (29) and (30) are added to the cooled solution of cyanuric halide (28).
- the technique is preferred.
- Components added later may be added neat or in a solution dissolved in an organic solvent as described above, but the latter method is preferred in view of ease of operation and ease of reaction control. It is. The addition may be gradually added by dropping or the like, or may be added all at once.
- the target copolymerized triazine ring does not gel. A containing hyperbranched polymer can be obtained.
- various bases usually used at the time of polymerization or after polymerization may be added.
- this base include potassium carbonate, potassium hydroxide, sodium carbonate, sodium hydroxide, sodium hydrogen carbonate, sodium ethoxide, sodium acetate, lithium carbonate, lithium hydroxide, lithium oxide, potassium acetate, magnesium oxide, oxidized Calcium, barium hydroxide, trilithium phosphate, trisodium phosphate, tripotassium phosphate, cesium fluoride, aluminum oxide, ammonia, trimethylamine, triethylamine, diisopropylmethylamine, diisopropylethylamine, N-methylpiperidine, 2,2, Examples include 6,6-tetramethyl-N-methylpiperidine, pyridine, 4-dimethylaminopyridine, N-methylmorpholine and the like.
- the addition amount of the base is preferably 1 to 100 equivalents, more preferably 1 to 10 equivalents per 1 equivalent of cyanuric halide (28). These bases may be used as an aqueous solution. In the polymer obtained, it is preferable that no raw material components remain, but some raw materials may remain as long as the effects of the present invention are not impaired. In any of the scheme methods, after completion of the reaction, the product can be easily purified by a reprecipitation method or the like.
- At least one of the halogen atoms of the terminal triazine ring is substituted with an alkyl group, an aralkyl group, an aryl group, an alkylamino group, an alkoxysilyl group-containing alkylamino group, an aralkylamino group, an arylamino group, You may cap by an alkoxy group, an aralkyloxy group, an aryloxy group, an ester group, etc.
- an alkylamino group, an alkoxysilyl group-containing alkylamino group, an aralkylamino group, and an arylamino group are preferable, an alkylamino group and an arylamino group are more preferable, and an arylamino group is further preferable.
- ester group examples include a methoxycarbonyl group and an ethoxycarbonyl group.
- alkylamino group include methylamino group, ethylamino group, n-propylamino group, isopropylamino group, n-butylamino group, isobutylamino group, s-butylamino group, t-butylamino group, n -Pentylamino group, 1-methyl-n-butylamino group, 2-methyl-n-butylamino group, 3-methyl-n-butylamino group, 1,1-dimethyl-n-propylamino group, 1,2 -Dimethyl-n-propylamino group, 2,2-dimethyl-n-propylamino group, 1-ethyl-n-propylamino group, n-hexylamino group, 1-methyl-n-pentylamino group, 2-methyl -N-p
- aralkylamino group examples include benzylamino group, methoxycarbonylphenylmethylamino group, ethoxycarbonylphenylmethylamino group, p-methylphenylmethylamino group, m-methylphenylmethylamino group, and o-ethylphenylmethylamino group.
- arylamino group examples include phenylamino group, methoxycarbonylphenylamino group, ethoxycarbonylphenylamino group, naphthylamino group, methoxycarbonylnaphthylamino group, ethoxycarbonylnaphthylamino group, anthranylamino group, pyrenylamino group, biphenylamino. Group, terphenylamino group, fluorenylamino group and the like.
- the alkoxysilyl group-containing alkylamino group may be any of a monoalkoxysilyl group-containing alkylamino group, a dialkoxysilyl group-containing alkylamino group, or a trialkoxysilyl group-containing alkylamino group.
- aryloxy group examples include a phenoxy group, a naphthoxy group, an anthranyloxy group, a pyrenyloxy group, a biphenyloxy group, a terphenyloxy group, and a fluorenyloxy group.
- aralkyloxy group examples include benzyloxy group, p-methylphenylmethyloxy group, m-methylphenylmethyloxy group, o-ethylphenylmethyloxy group, m-ethylphenylmethyloxy group, p-ethylphenylmethyl group.
- Examples include an oxy group, 2-propylphenylmethyloxy group, 4-isopropylphenylmethyloxy group, 4-isobutylphenylmethyloxy group, ⁇ -naphthylmethyloxy group, and the like.
- examples of the alkyl group, the aralkyl group, and the aryl group include the same groups as those described above. These groups can be easily introduced by substituting the halogen atom on the triazine ring with a compound that gives a corresponding substituent. For example, as shown in the following scheme 3, the reaction is carried out by adding an aniline derivative. By doing so, a hyperbranched polymer (33) having a phenylamino group at at least one terminal is obtained.
- the organic monoamine is simultaneously charged, that is, by reacting the cyanuric halide compound with the diaminoaryl compound in the presence of the organic monoamine, the rigidity of the hyperbranched polymer is reduced, and the degree of branching is reduced.
- a low soft hyperbranched polymer can be obtained.
- the hyperbranched polymer obtained by this method has excellent solubility in a solvent (inhibition of aggregation) and crosslinkability with a crosslinking agent, and is particularly used when used as a composition in combination with a crosslinking agent described later. It is advantageous.
- the organic monoamine any of alkyl monoamine, aralkyl monoamine, and aryl monoamine can be used as the organic monoamine.
- Alkyl monoamines include methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, s-butylamine, t-butylamine, n-pentylamine, 1-methyl-n-butylamine, 2-methyl- n-butylamine, 3-methyl-n-butylamine, 1,1-dimethyl-n-propylamine, 1,2-dimethyl-n-propylamine, 2,2-dimethyl-n-propylamine, 1-ethyl-n -Propylamine, n-hexylamine, 1-methyl-n-pentylamine, 2-methyl-n-pentylamine, 3-methyl-n-pentylamine, 4-methyl-n-pentylamine, cyclohexylamine, 1, 1-dimethyl-n-butylamine, 1,2-dimethyl-n-butylamine 1,3-dimethyl-n
- aralkyl monoamines include benzylamine, p-methoxycarbonylbenzylamine, p-ethoxycarbonylbenzylamine, p-methylbenzylamine, m-methylbenzylamine, o-methoxybenzylamine and the like.
- aryl monoamine examples include aniline, p-methoxycarbonylaniline, p-ethoxycarbonylaniline, p-methoxyaniline, 1-naphthylamine, 2-naphthylamine, anthranylamine, 1-aminopyrene, 4-biphenylylamine, o- And phenylaniline, 4-amino-p-terphenyl, 2-aminofluorene, and the like.
- the amount of the organic monoamine used is preferably 0.05 to 500 equivalents, more preferably 0.05 to 120 equivalents, and even more preferably 0.05 to 50 equivalents per equivalent of the cyanuric halide compound.
- the reaction temperature is preferably 60 to 150 ° C., preferably 80 to 150 ° C., and preferably 80 to 120 ° C. from the viewpoint of suppressing linearity and increasing the degree of branching.
- the mixing of the three components of the organic monoamine, the halogenated cyanuric compound and the diaminoaryl compound may be performed at a low temperature.
- the temperature is preferably about ⁇ 50 to 50 ° C., and about ⁇ 20 to 50 ° C.
- the reaction After the low temperature charging, it is preferable to carry out the reaction by raising the temperature to the polymerization temperature at once (in one step). Further, the two components of the cyanuric halide compound and the diaminoaryl compound may be mixed at a low temperature. In this case, the temperature is preferably about ⁇ 50 to 50 ° C., more preferably about ⁇ 20 to 50 ° C., More preferably, it is ⁇ 20 to 10 ° C. It is preferable to carry out the reaction by adding an organic monoamine after the low-temperature charging and raising the temperature to a temperature for polymerization (in one step). Moreover, you may perform reaction which makes a halogenated cyanuric compound and a diaminoaryl compound react with presence of such an organic monoamine using the organic solvent similar to the above-mentioned.
- the polymer of the present invention described above can be used as a composition mixed with other compounds, and examples thereof include a composition with a leveling agent, a surfactant, a crosslinking agent, a resin and the like. These compositions can be used as a film-forming composition, and can be suitably used as a film-forming composition (also referred to as a polymer varnish) dissolved in various solvents.
- the solvent used for dissolving the polymer may be the same as or different from the solvent used during the polymerization.
- the solvent is not particularly limited as long as the compatibility with the polymer is not impaired, and one kind or a plurality of kinds can be arbitrarily selected and used.
- solvents include toluene, p-xylene, o-xylene, m-xylene, ethylbenzene, styrene, ethylene glycol dimethyl ether, propylene glycol monomethyl ether, ethylene glycol monomethyl ether, propylene glycol, propylene glycol monoethyl ether.
- Ethylene glycol monoethyl ether ethylene glycol monoisopropyl ether, ethylene glycol methyl ether acetate, propylene glycol monomethyl ether acetate, ethylene glycol ethyl ether acetate, diethylene glycol dimethyl ether, propylene glycol monobutyl ether, ethylene glycol monobutyl ether, diethylene glycol diethyl ether, dipro Lenglycol monomethyl ether, diethylene glycol monomethyl ether, dipropylene glycol monoethyl ether, diethylene glycol monoethyl ether, triethylene glycol dimethyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol, 1-octanol, ethylene glycol, hexylene glycol, trimethylene glycol, 1 -Methoxy-2-butanol, cyclohexanol, diacetone alcohol, furfuryl alcohol, tetrahydrofurfury
- the solid content concentration in the film-forming composition is not particularly limited as long as it does not affect the storage stability, and may be appropriately set according to the target film thickness.
- the solid content concentration is preferably 0.1 to 50% by mass, and more preferably 0.1 to 20% by mass.
- the film-forming composition of the present invention contains other components other than the triazine ring-containing polymer and the solvent, for example, a leveling agent, a surfactant, a crosslinking agent, and the like. Also good.
- surfactant examples include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene oleyl ether; polyoxyethylene octylphenol ether, polyoxyethylene nonylphenol Polyoxyethylene alkyl allyl ethers such as ethers; polyoxyethylene / polyoxypropylene block copolymers; sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan tristearate Sorbitan fatty acid esters such as polyoxyethylene sorbitan monolaurate, polyoxyethyleneso Nonionic surfactants such as polyoxyethylene sorbitan fatty acid esters such as bitane monopalmitate, polyoxyethylene sorbitan monostearate, polyoxyethylene sorbitan trioleate, polyoxyethylene sorbitan tristearate, trade name
- Fluorosurfactant such as FLORARD FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), trade names Asahi Guard AG710, Surflon S-382, SC101, SC102, SC103, SC104, SC105, SC106 (Asahi Glass Co., Ltd.) Agent Ganosiloxane polymer KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), BYK-302, BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-370, BYK-375, BYK-378 ( Big Chemie Japan Co., Ltd.).
- surfactants may be used alone or in combination of two or more.
- the amount of the surfactant used is preferably 0.0001 to 5 parts by mass, more preferably 0.001 to 1 part by mass, and 0.01 to 0.5 parts by mass with respect to 100 parts by mass of the triazine ring-containing polymer. Even more preferred.
- the crosslinking agent is not particularly limited as long as it is a compound having a substituent capable of reacting with the triazine ring-containing polymer of the present invention.
- examples of such compounds include melamine compounds having a crosslinkable substituent such as a methylol group and methoxymethyl group, substituted urea compounds, compounds containing a crosslinkable substituent such as an epoxy group or an oxetane group, and blocked isocyanates.
- the blocked isocyanate group is also preferable from the viewpoint that the refractive index does not decrease because it is crosslinked by a urea bond and has a carbonyl group.
- an epoxy compound it has two or more epoxy groups in one molecule, and when exposed to a high temperature during thermosetting, the epoxy is ring-opened and crosslinked with the triazine ring-containing polymer of the present invention by an addition reaction. The reaction proceeds.
- crosslinking agent examples include tris (2,3-epoxypropyl) isocyanurate, 1,4-butanediol diglycidyl ether, 1,2-epoxy-4- (epoxyethyl) cyclohexane, glycerol triglycidyl ether, diethylene glycol Diglycidyl ether, 2,6-diglycidylphenyl glycidyl ether, 1,1,3-tris [p- (2,3-epoxypropoxy) phenyl] propane, 1,2-cyclohexanedicarboxylic acid diglycidyl ester, 4,4 '-Methylenebis (N, N-diglycidylaniline), 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, trimethylolethane triglycidyl ether, bisphenol-A-diglycidyl ether, pentae Examples include lithi
- epoxy resins having at least two epoxy groups YH-434, YH434L (manufactured by Tohto Kasei Co., Ltd.), epoxy resins having a cyclohexene oxide structure, Epolide GT-401 and GT -403, GT-301, GT-302, Celoxide 2021, 3000 (manufactured by Daicel Chemical Industries, Ltd.), bisphenol A type epoxy resin, Epicoat (currently jER) 1001, 1002, 1003, 1004, 1007, 1009, 1010, 828 (Japan Epoxy Resin Co., Ltd.), Bisphenol F type epoxy resin, Epicoat (currently jER) 807 (Japan Epoxy Resin Co., Ltd.) , Epicoat (a phenol novolac type epoxy resin) , JER) 152, 154 (above, manufactured by Japan Epoxy Resins Co., Ltd.), EPPN 201, 202 (above, manufactured by Nippon Kayaku Co., Ltd.
- EX-612, EX-614, EX-622, EX-411, EX-512, EX-522, EX-522, EX-421, EX-313, EX-314, EX-321 can also be used.
- the acid anhydride compound is a carboxylic acid anhydride obtained by dehydrating and condensing two molecules of carboxylic acid. When exposed to a high temperature during thermosetting, the anhydride ring is opened and the triazine ring of the present invention is contained. A crosslinking reaction proceeds with the polymer by an addition reaction.
- Specific examples of the acid anhydride compound include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, nadic anhydride, methyl nadic anhydride, maleic anhydride.
- (meth) acrylic compound As a (meth) acrylic compound, it has two or more (meth) acrylic groups in one molecule, and when exposed to a high temperature during thermosetting, it undergoes an addition reaction with the triazine ring-containing polymer of the present invention. The crosslinking reaction proceeds.
- Examples of the compound having a (meth) acryl group include ethylene glycol diacrylate, ethylene glycol dimethacrylate, polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, ethoxylated bisphenol A diacrylate, ethoxylated bisphenol A dimethacrylate, and ethoxylated tri Methylolpropane triacrylate, ethoxylated trimethylolpropane trimethacrylate, ethoxylated glycerin triacrylate, ethoxylated glycerin trimethacrylate, ethoxylated pentaerythritol tetraacrylate, ethoxylated pentaerythritol tetramethacrylate, ethoxylated dipentaerythritol hexaacrylate, polyglycerol mono Ethylene oxide polyacrylate Polyglycerin polyethylene glycol polyacrylate, dipentaerythrito
- the compound having the (meth) acryl group is available as a commercial product. Specific examples thereof include NK ester A-200, same A-400, same A-600, same A-1000, same A- TMPT, UA-53H, 1G, 2G, 3G, 4G, 9G, 14G, 23G, ABE-300, A-BPE-4, A-BPE-6, A- BPE-10, A-BPE-20, A-BPE-30, BPE-80N, BPE-100N, BPE-200, BPE-500, BPE-900, BPE-1300N, A -GLY-3E, A-GLY-9E, A-GLY-20E, A-TMPT-3EO, A-TMPT-9EO, ATM-4E, ATM-35E KAYAR) D (registered trademark) DPEA-12, PEG400DA, THE-330, RP-1040 (above, Nippon Kayaku Co., Ltd.), M-210, M-350 (above, Toagosei Co
- the isocyanate group (—NCO) has two or more blocked isocyanate groups blocked by an appropriate protective group in one molecule and is exposed to a high temperature during thermal curing
- the protecting group (block portion) is dissociated by thermal dissociation, and the resulting isocyanate group causes a crosslinking reaction with the resin.
- two or more groups represented by the following formula in one molecule (note these The groups may be the same or different from each other).
- R b represents an organic group in the block part.
- Such a compound can be obtained, for example, by reacting an appropriate blocking agent with a compound having two or more isocyanate groups in one molecule.
- the compound having two or more isocyanate groups in one molecule include, for example, isophorone diisocyanate, 1,6-hexamethylene diisocyanate, methylene bis (4-cyclohexyl isocyanate), polyisocyanate of trimethylhexamethylene diisocyanate, and dimers thereof. , Trimers, and reaction products of these with diols, triols, diamines, or triamines.
- the blocking agent examples include alcohols such as methanol, ethanol, isopropanol, n-butanol, 2-ethoxyhexanol, 2-N, N-dimethylaminoethanol, 2-ethoxyethanol, cyclohexanol; phenol, o-nitrophenol , P-chlorophenol, phenols such as o-, m- or p-cresol; lactams such as ⁇ -caprolactam, oximes such as acetone oxime, methyl ethyl ketone oxime, methyl isobutyl ketone oxime, cyclohexanone oxime, acetophenone oxime, benzophenone oxime
- pyrazoles such as pyrazole, 3,5-dimethylpyrazole and 3-methylpyrazole
- thiols such as dodecanethiol and benzenethiol.
- a compound containing a blocked isocyanate is also available as a commercial product.
- Specific examples thereof include B-830, B-815N, B-842N, B-870N, B-874N, B-882N, B -7005, B-7030, B-7075, B-5010 (Mitsui Chemicals Polyurethane Co., Ltd.), Duranate (registered trademark) 17B-60PX, TPA-B80E, MF-B60X, MF-K60X, E402-B80T (above, manufactured by Asahi Kasei Chemicals Corporation), Karenz MOI-BM (registered trademark) (above, manufactured by Showa Denko Co., Ltd.), and the like.
- an aminoplast compound As an aminoplast compound, it has two or more methoxymethylene groups in one molecule, and when exposed to a high temperature during thermosetting, it undergoes a crosslinking reaction by a demethanol condensation reaction with the triazine ring-containing polymer of the present invention. Is something that progresses.
- Examples of the melamine-based compound include Cymel series such as hexamethoxymethylmelamine CYMEL (registered trademark) 303, tetrabutoxymethylglycoluril 1170, tetramethoxymethylbenzoguanamine 1123 (above, manufactured by Nihon Cytec Industries, Ltd.), Nicalac (registered trademark) MW-30HM, MW-390, MW-100LM, MX-750LM, which are methylated melamine resins, MX-270, MX-280, MX-290, which are methylated urea resins. (Nicarak series, etc., manufactured by Sanwa Chemical Co., Ltd.).
- Cymel series such as hexamethoxymethylmelamine CYMEL (registered trademark) 303, tetrabutoxymethylglycoluril 1170, tetramethoxymethylbenzoguanamine 1123 (above, manufactured by Nihon Cytec Industries, Ltd.), Nicalac (register
- the oxetane compound has two or more oxetanyl groups in one molecule and undergoes a crosslinking reaction by an addition reaction with the triazine ring-containing polymer of the present invention when exposed to a high temperature during thermosetting. It is.
- the compound having an oxetane group include OX-221-containing oxetane group, OX-SQ-H, and OX-SC (manufactured by Toagosei Co., Ltd.).
- the phenoplast compound has two or more hydroxymethylene groups in one molecule and undergoes a crosslinking reaction by dehydration condensation reaction with the triazine ring-containing polymer of the present invention when exposed to a high temperature during thermosetting. It is a progression.
- phenoplast compound examples include 2,6-dihydroxymethyl-4-methylphenol, 2,4-dihydroxymethyl-6-methylphenol, bis (2-hydroxy-3-hydroxymethyl-5-methylphenyl) methane, Bis (4-hydroxy-3-hydroxymethyl-5-methylphenyl) methane, 2,2-bis (4-hydroxy-3,5-dihydroxymethylphenyl) propane, bis (3-formyl-4-hydroxyphenyl) methane Bis (4-hydroxy-2,5-dimethylphenyl) formylmethane, ⁇ , ⁇ -bis (4-hydroxy-2,5-dimethylphenyl) -4-formyltoluene and the like.
- the phenoplast compound is also available as a commercial product, and specific examples thereof include 26DMPC, 46DMOC, DM-BIPC-F, DM-BIOC-F, TM-BIP-A, BISA-F, BI25X-DF. BI25X-TPA (above, manufactured by Asahi Organic Materials Co., Ltd.).
- crosslinking agents may be used alone or in combination of two or more.
- the amount of the crosslinking agent used is preferably 1 to 100 parts by mass with respect to 100 parts by mass of the triazine ring-containing polymer, but considering the solvent resistance, the lower limit is preferably 10 parts by mass, more preferably 20 parts by mass. Furthermore, in consideration of controlling the refractive index, the upper limit is preferably 50 parts by mass, more preferably 30 parts by mass.
- the crosslinking agent and the reactive terminal substituent of the triazine ring-containing polymer react with each other, and effects such as improved film density, improved heat resistance, and improved thermal relaxation ability can be achieved There is.
- the said other component can be added at the arbitrary processes at the time of preparing the composition of this invention.
- the film-forming composition of the present invention can be applied to a substrate and then heated as necessary to form a desired film.
- the coating method of the composition is arbitrary, for example, spin coating method, dip method, flow coating method, ink jet method, spray method, bar coating method, gravure coating method, slit coating method, roll coating method, transfer printing method, brush Methods such as coating, blade coating, and air knife coating can be employed.
- the firing temperature is not particularly limited for the purpose of evaporating the solvent, and can be performed at 40 to 400 ° C., for example. In these cases, the temperature may be changed in two or more steps for the purpose of expressing a higher uniform film forming property or allowing the reaction to proceed on the substrate.
- the baking method is not particularly limited, and for example, it may be evaporated using a hot plate or an oven in an appropriate atmosphere such as air, an inert gas such as nitrogen, or in a vacuum.
- the firing temperature and firing time may be selected in accordance with the process steps of the target electronic device, and the firing conditions may be selected so that the physical properties of the obtained film meet the required characteristics of the electronic device.
- the film made of the composition of the present invention thus obtained can achieve high heat resistance, high transparency, high refractive index, high solubility, and low volume shrinkage, so that it can be used for liquid crystal displays, organic electroluminescence (EL ) It can be suitably used as a member for producing electronic devices such as displays, optical semiconductor (LED) elements, solid-state imaging elements, organic thin film solar cells, dye-sensitized solar cells, and organic thin film transistors (TFTs).
- LED optical semiconductor
- TFTs organic thin film transistors
- thermoplastic resin examples include polyolefin resins such as PE (polyethylene), PP (polypropylene), EVA (ethylene-vinyl acetate copolymer), EEA (ethylene-ethyl acrylate copolymer); PS (polystyrene) Polystyrene resins such as HIPS (high impact polystyrene), AS (acrylonitrile-styrene copolymer), ABS (acrylonitrile-butadiene-styrene copolymer), MS (methyl methacrylate-styrene copolymer); polycarbonate resin; Polyvinyl resin; Polyamide resin; (Meth) acrylic resin such as PMMA (polymethyl methacrylate); PET (polyethylene terephthalate), polybutylene terephthalate, polyethylene naphthalate
- thermosetting resins examples include phenol resin, urea resin, melamine resin, unsaturated polyester resin. , Polyurethane resin, epoxy resin and the like. These resins may be used alone or in combination of two or more, and the amount used is preferably 1 to 10,000 parts by mass with respect to 100 parts by mass of the triazine ring-containing polymer. The amount is preferably 1 to 1,000 parts by mass.
- a composition with a (meth) acrylic resin can be obtained by blending a (meth) acrylate compound into the composition and polymerizing the (meth) acrylate compound.
- (meth) acrylate compounds include methyl (meth) acrylate, ethyl (meth) acrylate, ethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (Meth) acrylate, polypropylene glycol di (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, trimethylolpropane tri Oxyethyl (meth) acrylate, tricyclodecane dimethanol di (meth) acrylate, tricyclodecany
- Polymerization of these (meth) acrylate compounds can be carried out by light irradiation or heating in the presence of a photo radical initiator or a heat radical initiator.
- a photo radical initiator or a heat radical initiator examples include acetophenones, benzophenones, Michler's benzoylbenzoate, amyloxime ester, tetramethylthiuram monosulfide, and thioxanthones.
- photocleavable photoradical polymerization initiators are preferred.
- the photocleavable photoradical polymerization initiator is described in the latest UV curing technology (p. 159, publisher: Kazuhiro Takahisa, publisher: Technical Information Association, Inc., published in 1991).
- radical photopolymerization initiators are, for example, trade names: Irgacure 184, 369, 651, 500, 819, 907, 784, 2959, CGI 1700, CGI 1750, CGI 1850, CG24-61, Darocur, manufactured by Ciba Japan 1116, 1173, manufactured by BASF, Inc.
- Product name Lucillin TPO, manufactured by UCB, Inc.
- Product name Ubekrill P36, manufactured by Fratteri Lamberti, Inc.
- the photopolymerization initiator is preferably used in the range of 0.1 to 15 parts by mass, more preferably 1 to 10 parts by mass with respect to 100 parts by mass of the (meth) acrylate compound.
- the solvent used for the polymerization include the same solvents as those exemplified above for the film-forming composition.
- DMAc dimethylacetamide
- the filtrate was reprecipitated into a mixed solution of 28% aqueous ammonia (182.14 g) and ion-exchanged water 3367 g.
- the precipitate was filtered, redissolved in 422 g of THF, and reprecipitated in a mixed solution of 3000 g of ion-exchanged water and 100 g of methanol.
- the resulting precipitate was filtered and dried at 150 ° C. for 8 hours in a vacuum dryer to obtain 73.33 g of the target polymer compound [4] (hereinafter abbreviated as HB-TDFA03).
- the measurement result of 1 H-NMR spectrum of HB-TDFA03 is shown in FIG.
- the obtained HB-TDFA03 is a compound having a structural unit represented by the formula (1).
- the weight average molecular weight Mw measured by GPC (THF system) of HB-TDFA03 in terms of polystyrene was 5,400, and the polydispersity Mw / Mn was 4.05.
- Example 2 Measurement of 5% weight loss of HB-TDFA03 5.73 mg of HB-TDFA03 obtained in Example 1 was added to a platinum pan, and measurement was performed with TG-DTA at a temperature elevation rate of 15 ° C / min. The result is shown in FIG. The 5% weight loss was 408 ° C. Further, when the glass transition temperature was measured by DSC measurement, a transition point was observed at 227 ° C.
- Example 3 Refractive Index Measurement HB-TDFA03 (0.1 g) obtained in Example 1 was dissolved in 0.9 g of cyclohexanone to obtain a light yellow transparent solution.
- the obtained polymer varnish was spin-coated on a glass substrate using a spin coater at 200 rpm for 5 seconds and 2000 rpm for 30 seconds, heated at 100 ° C. for 1 minute, and 300 ° C. for 5 minutes to remove the solvent, and a film was obtained. It was.
- the refractive index of the obtained film was measured, the refractive index at 550 nm was 1.772.
- Example 4 Synthesis of polymer compound [4] The amount charged was 2,4,6-trichloro-1,3,5-triazine [1] (33.19 g, 0.18 mol, manufactured by Evonik Degussa). , M-phenylenediamine [2] (23.85 g, 0.22 mol), bisaminophenylfluorene [3] (8.55 g, 0.024 mol) and aniline (5.7 g, 0.06 mol), The reaction was carried out in the same manner as in Example 1 to obtain 57.19 g of the target polymer compound [4] (hereinafter abbreviated as HB-TDFA10).
- HB-TDFA10 target polymer compound [4]
- the measurement result of 1 H-NMR spectrum of HB-TDFA10 is shown in FIG.
- the obtained HB-TDFA10 is a compound having a structural unit represented by the formula (1).
- the weight average molecular weight Mw measured in terms of polystyrene by GPC (THF system) of HB-TDFA10 was 6,200, and the polydispersity Mw / Mn was 4.53.
- Example 5 Measurement of 5% weight loss of HB-TDFA10 TG-DTA measurement of HB-TDFA10 obtained in Example 4 was conducted in the same manner as in Example 2. As a result, the 5% weight loss was 414 ° C. there were. The result is shown in FIG.
- Example 6 Measurement of refractive index HB-TDFA10 (0.1 g) obtained in Example 4 was dissolved in 0.9 g of cyclohexanone to obtain a light yellow transparent solution.
- the obtained polymer varnish was spin-coated on a glass substrate using a spin coater at 200 rpm for 5 seconds and 2000 rpm for 30 seconds, heated at 100 ° C. for 1 minute, and 300 ° C. for 5 minutes to remove the solvent, and a film was obtained. It was.
- the refractive index of the obtained film was measured, the refractive index at 550 nm was 1.764.
- Example 7 Synthesis of polymer compound [4] The amount charged was 2,4,6-trichloro-1,3,5-triazine [1] (3.38 g, 0.018 mol, manufactured by Evonik Degussa). , M-phenylenediamine [2] (1.70 g, 0.015 mol), bisaminophenylfluorene [3] (2.37 g, 0.007 mol) and aniline (0.57 g, 0.06 mol), The reaction was conducted in the same manner as in Example 1 to obtain 5.79 g of the target polymer compound [4] (hereinafter abbreviated as HB-TDFA30). The measurement result of 1 H-NMR spectrum of HB-TDFA30 is shown in FIG.
- the obtained HB-TDFA30 is a compound having a structural unit represented by the formula (1).
- the weight average molecular weight Mw measured by GPC (THF system) of HB-TDFA30 in terms of polystyrene was 5,800, and the polydispersity Mw / Mn was 2.78.
- Example 8 Measurement of 5% weight loss of HB-TDFA30 TG-DTA measurement of HB-TDFA30 obtained in Example 7 was performed in the same manner as in Example 2. As a result, the 5% weight loss was 423 ° C. there were. The result is shown in FIG.
- Example 9 Refractive Index Measurement HB-TDFA30 (0.1 g) obtained in Example 7 was dissolved in 0.9 g of cyclohexanone to obtain a light yellow transparent solution.
- the obtained polymer varnish was spin-coated on a glass substrate using a spin coater at 200 rpm for 5 seconds and 2000 rpm for 30 seconds, heated at 100 ° C. for 1 minute, and 300 ° C. for 5 minutes to remove the solvent, and a film was obtained. It was. When the refractive index of the obtained film was measured, the refractive index at 550 nm was 1.762.
- Example 10 Synthesis of polymer compound [4] The amount charged was 2,4,6-trichloro-1,3,5-triazine [1] (3.33 g, 0.018 mol, manufactured by Evonik Degussa). , M-phenylenediamine [2] (1.23 g, 0.011 mol), bisaminophenylfluorene [3] (3.92 g, 0.011 mol) and aniline (0.59 g, 0.06 mol), The reaction was conducted in the same manner as in Example 1 to obtain 6.65 g of the target polymer compound [4] (hereinafter abbreviated as HB-TDFA50). The measurement result of 1 H-NMR spectrum of HB-TDFA50 is shown in FIG.
- the obtained HB-TDFA50 is a compound having a structural unit represented by the formula (1).
- the weight average molecular weight Mw measured by GPC (THF system) of HB-TDFA50 in terms of polystyrene was 6,400, and the polydispersity Mw / Mn was 2.80.
- Example 11 Measurement of 5% weight loss of HB-TDFA50
- the TG-DTA measurement of HB-TDFA50 obtained in Example 10 was performed in the same manner as in Example 2. As a result, the 5% weight loss was 465 ° C. there were. The result is shown in FIG.
- Example 12 Refractive index measurement HB-TDFA50 (0.1 g) obtained in Example 10 was dissolved in 0.9 g of cyclohexanone to obtain a light yellow transparent solution.
- the obtained polymer varnish was spin-coated on a glass substrate using a spin coater at 200 rpm for 5 seconds and 2000 rpm for 30 seconds, heated at 100 ° C. for 1 minute, and 300 ° C. for 5 minutes to remove the solvent, and a film was obtained. It was.
- the refractive index of the obtained film was measured, the refractive index at 550 nm was 1.750.
- Example 13 Refractive index adjustment, thermosetting test
- the HB-TDFA50 obtained in Example 10 was 10, 30, 50 against dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) as a crosslinking agent.
- the cyclohexanone solution having a solid content of 10% by mass was prepared, and spin coating was performed on the glass substrate at 200 rpm, 5 seconds, 1500 rpm, and 30 seconds. Thereafter, baking was performed at 100 ° C. for 1 minute and at 250 ° C. for 5 minutes to remove the solvent.
- the refractive index and film thickness of each obtained coating film were measured. The results are shown in Table 1.
- Example 14 The coating film produced in Example 13 was immersed in cyclohexanone, and after 5 minutes, spray drying was performed, and the refractive index and film thickness were measured in the same manner as in Example 13. The results are also shown in Table 1.
- thermosetting As shown in Table 1, no significant change in refractive index or film thickness is observed after thermosetting, indicating that the composition can be used as a thermosetting composition.
- amount of hyperbranched polymer (HB-TDFA50) added As shown in Table 1, no significant change in refractive index or film thickness is observed after thermosetting, indicating that the composition can be used as a thermosetting composition.
- the amount of hyperbranched polymer (HB-TDFA50) added increased, the refractive index improved, confirming that the polymer can be used as a refractive index modifier.
- Example 15 HB-TDFA50 obtained in Example 10 was added in an amount of 10, 30, 50, 70% by mass to Takenate B882N (Mitsui Chemical Co., Ltd.), which is a crosslinking agent, and a cyclohexanone solution having a solid content of 10% by mass was added.
- the glass substrate was spin-coated at 200 rpm, 5 seconds, 1500 rpm, 30 seconds. Thereafter, baking was performed at 100 ° C. for 1 minute and at 250 ° C. for 5 minutes to remove the solvent. The refractive index and film thickness of the obtained coating film were measured. The results are shown in Table 2.
- Example 16 The coating film produced in Example 15 was immersed in cyclohexanone, and after 5 minutes, spray drying was performed. The refractive index and film thickness were measured in the same manner as in Example 15. The results are also shown in Table 2.
- thermosetting composition can be used as a thermosetting composition.
- amount of hyperbranched polymer (HB-TDFA50) added increased, the refractive index improved, confirming that the polymer can be used as a refractive index modifier.
- the obtained HB-TAM-mDA is a compound having a structural unit represented by the formula (1).
- the weight average molecular weight Mw measured in terms of polystyrene by GPC (DMF system) of HB-TAM-mDA was 185,000, and the polydispersity Mw / Mn was 39.2.
- Example 18 Measurement of 5% weight loss of HB-TAM-mDA
- TG-DTA measurement of HB-TAM-mDA obtained in Example 17 was performed.
- Example 19 Measurement of refractive index HB-TAM-mDA (0.1 g) obtained in Example 17 was dissolved in 0.9 g of cyclohexanone to obtain a pale yellow transparent solution.
- the obtained polymer varnish was spin-coated on a glass substrate using a spin coater at 200 rpm for 5 seconds and 2000 rpm for 30 seconds, heated at 100 ° C. for 1 minute, and 300 ° C. for 5 minutes to remove the solvent, and a film was obtained. It was.
- the refractive index of the obtained film was measured, the refractive index at 550 nm was 1.843.
- the obtained HB-TAM-mDA is a compound having a structural unit represented by the formula (1).
- the weight average molecular weight Mw measured in terms of polystyrene by GPC (DMF system) of HB-TAM-FA was 183,000, and the polydispersity Mw / Mn was 55.9.
- Example 21 Measurement of 5% weight loss of HB-TAM-FA
- TG-DTA measurement of HB-TAM-FA obtained in Example 20 was performed in the same manner as in Example 2, 5% weight loss was measured.
- 5% weight loss was measured.
- Example 22 Refractive Index Measurement HB-TAM-FA (0.1 g) obtained in Example 20 was dissolved in 0.9 g of cyclohexanone to obtain a light yellow transparent solution.
- the obtained polymer varnish was spin-coated on a glass substrate using a spin coater at 200 rpm for 5 seconds and 2000 rpm for 30 seconds, heated at 100 ° C. for 1 minute, and 300 ° C. for 5 minutes to remove the solvent, and a film was obtained. It was. When the refractive index of the obtained film was measured, the refractive index at 550 nm was 1.818.
- Reagents and amounts charged were 2,4,6-trichloro-1,3,5-triazine [1] (23.05 g, 0.125 mol, manufactured by Evonik Degussa), m-phenylenediamine [2] (5. 95 g, 0.0550 mol, manufactured by DuPont), 4,4′-diaminobenzanilide [5] (18.75 g, 0.0825 mol, manufactured by Seika Co., Ltd.) and aniline (34.92 g, 0.375 mol).
- the reaction was conducted in the same manner as in Example 1 to obtain 40.18 g of the target polymer compound [6] (hereinafter abbreviated as TAmD32).
- the measurement result of 1 H-NMR spectrum of TAmD32 is shown in FIG.
- the obtained TAmD32 is a compound having a structural unit represented by the formula (1).
- the weight average molecular weight Mw measured in terms of polystyrene by GPC (NMP system) of TAmD32 was 32,100, and the polydispersity Mw / Mn was 4.9.
- Example 24 5% weight loss measurement of TAmD32
- the TG-DTA measurement of TAmD32 obtained in Example 23 was performed, and the 5% weight reduction was 427 ° C. The result is shown in FIG.
- Example 25 Refractive index measurement TAmD32 (0.1 g) obtained in Example 23 was dissolved in 0.9 g of cyclohexanone to obtain a pale yellow transparent solution.
- the obtained polymer varnish was spin-coated on a glass substrate at 200 rpm for 5 seconds and 2000 rpm for 30 seconds using a spin coater, and the solvent was removed by heating at 100 ° C. for 1 minute and 250 ° C. for 5 minutes to obtain a film. It was.
- the refractive index of the obtained film was measured, the refractive index at 550 nm was 1.824.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Physics & Mathematics (AREA)
- Power Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Electromagnetism (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Computer Hardware Design (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Optics & Photonics (AREA)
- Inorganic Chemistry (AREA)
- Sustainable Development (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
例えば、シロキサンポリマーと、ジルコニアまたはチタニアなどを分散させた微粒子分散材料とを混合してなるハイブリッド材料を用いて屈折率を高める手法が報告されている(特許文献1)。
さらに、シロキサンポリマーの一部に高屈折率な縮合環状骨格を導入する手法も報告されている(特許文献2)。
これまで炭素および窒素からなる耐熱性有機材料としては、芳香族ポリイミドや芳香族ポリアミドが主として用いられているが、これらの材料は直鎖構造を有しているため耐熱温度はそれほど高くない。
また、耐熱性を有する含窒素高分子材料としてトリアジン系縮合材料も報告されている(特許文献4)。
求められる具体的な特性としては、1)耐熱性、2)透明性、3)高屈折率、4)高溶解性、5)低体積収縮率などが挙げられる。
しかし、上述した眼鏡用高屈折率レンズ用材料は一般的に耐熱性が乏しく、200℃以下の温度範囲で作製する必要があるため、大気下、300℃で焼成するなどのプロセスには不向きである。
また、芳香族環やトリアジン環を導入した高分子化合物は、一般的に溶媒への溶解性が不足しているため、安全性溶剤であるレジスト溶剤には不溶であり、一方、高溶解性を示す材料は、透明性が低いのが一般的である。
また、この材料は性質の異なる微粒子を含むことから、エッチングやアッシングなどのドライプロセスを経る場合、エッチレートが不安定となって均一な膜厚の被膜が得られにくく、デバイスを作製する際のプロセスマージンが狭くなるという問題もある。
ハイパーブランチポリマーとは、例えば、ABx型の多官能性モノマー(ここでAとBは互いに反応する官能基、Bの数Xは2以上)を重合させて得られる不規則な分岐構造を有する高分岐ポリマーである。
一方、デンドリマーとは、規則的な分岐構造を有する高分岐ポリマーである。ハイパーブランチポリマーは、デンドリマーより合成が容易であり、高分子量体も合成しやすいという特徴がある。
トリアジン環を有するハイパーブランチポリマーは難燃剤用途として合成された報告例がある(非特許文献1)。
この知見を基に、本発明者らは、さらなる検討を重ねた結果、屈折率、耐熱性、各種有機溶媒に対する溶解性により優れた共重合型のハイパーブランチポリマーを見出し、本発明を完成した。
1. 下記式(1)で表される繰り返し単位構造を含むことを特徴とするトリアジン環含有重合体、
で示される基を表す。〕}
2. 前記Ar1およびAr2の組み合わせが、前記式(5)~(12)および(14)~(18)で示される群から選ばれる2種である1のトリアジン環含有重合体、
3. 前記Ar1およびAr2の組み合わせが、前記式(7)、(11)、(12)、(14)および(15)で示される群から選ばれる2種である1のトリアジン環含有重合体、
4. 前記Ar1およびAr2の組み合わせが、下記式(20)~(24)で示される群から選ばれる2種である1のトリアジン環含有重合体、
5. 前記繰り返し単位構造が、式(25)を含む1のトリアジン環含有重合体、
9. 少なくとも1つのトリアジン環末端を有し、このトリアジン環末端が、アルキル基、アラルキル基、アリール基、アルキルアミノ基、アルコキシシリル基含有アルキルアミノ基、アラルキルアミノ基、アリールアミノ基、アルコキシ基、アラルキルオキシ基、アリールオキシ基、またはエステル基でキャップされている8のトリアジン環含有重合体、
10. 1~9のいずれかのトリアジン環含有重合体を含む膜形成用組成物、
11. 10の膜形成用組成物から得られる膜、
12. 1~9のいずれかのトリアジン環含有重合体を含む膜、
13. 基材と、この基材上に形成された11または12の膜とを備える電子デバイス、
14. 基材と、この基材上に形成された11または12の膜とを備える光学部材、
15. 11または12の膜を少なくとも1層備える、電荷結合素子または相補性金属酸化膜半導体からなる固体撮像素子、
16. 11または12の膜をカラーフィルター上の平坦化層として備える固体撮像素子、
17. 10の膜形成用組成物からなる、固体撮像素子用レンズ材料、平坦化材料または埋め込み材料
を提供する。
本発明の重合体骨格とすることで、1)2級アミンをポリマーのスペーサーとして用いる、2)末端に1級アミンが置換している、場合においても高耐熱性、高透明性を維持できる。
本発明のハイパーブランチポリマーが高屈折率を発現するのは、ハイパーブランチ型の構造にすることで、トリアジン環とアリール(Ar)部分が密に集まり、電子密度が上がっているためであると考えられる。
特に、上記R、R’、R”およびR'''の少なくとも1つが水素原子の場合、ハイパーブランチ型の構造にすることで、トリアジン環上の窒素原子とアミン部位の水素原子が水素結合し、よりトリアジン環とアリール(Ar)部分が密に集まり、電子密度が上がるものと考えられる。
また、高分子量の化合物であるにもかかわらず、各種有機溶媒に対する溶解性に優れるとともに、溶剤に溶解したときに低粘度であるため、ハンドリング性に優れる。
そして、金属酸化物を含まず、ポリマー単独で高屈折率を発現できることから、エッチングやアッシングなどのドライプロセスを経る場合でも、エッチレートが一定となり、均一な膜厚の被膜を得ることができ、デバイスを作製する際のプロセスマージンが拡大する。
また、本発明のトリアジン環含有重合体は、高耐熱性絶縁材料として使用できる。
以上のような特性を有する本発明のトリアジン環含有重合体を用いて作製した膜は、液晶ディスプレイ、有機エレクトロルミネッセンス(EL)ディスプレイ、光半導体(LED)素子、固体撮像素子、有機薄膜太陽電池、色素増感太陽電池、有機薄膜トランジスタ(TFT)などの電子デバイスを作製する際の一部材として好適に利用できる。
特に高屈折率が求められている固体撮像素子の部材である、フォトダイオード上の埋め込み膜および平坦化膜、カラーフィルター前後の平坦化膜、マイクロレンズ、マイクロレンズ上の平坦化膜およびコンフォーマル膜として好適に利用できる。
本発明に係るトリアジン環含有重合体は下記式(1)で表される繰り返し単位構造を含むものである。
本発明において、アルキル基の炭素数としては特に限定されるものではないが、1~20が好ましく、ポリマーの耐熱性をより高めることを考慮すると、炭素数1~10がより好ましく、1~3がより一層好ましい。また、その構造は、鎖状、分岐状、環状のいずれでもよい。
アルコキシ基の具体例としては、メトキシ基、エトキシ基、n-プロポキシ基、イソプロポキシ基、n-ブトキシ基、イソブトキシ基、s-ブトキシ基、t-ブトキシ基、n-ペントキシ基、1-メチル-n-ブトキシ基、2-メチル-n-ブトキシ基、3-メチル-n-ブトキシ基、1,1-ジメチル-n-プロポキシ基、1,2-ジメチル-n-プロポキシ基、2,2-ジメチル-n-プロポキシ基、1-エチル-n-プロポキシ基、n-ヘキシルオキシ基、1-メチル-n-ペンチルオキシ基、2-メチル-n-ペンチルオキシ基、3-メチル-n-ペンチルオキシ基、4-メチル-n-ペンチルオキシ基、1,1-ジメチル-n-ブトキシ基、1,2-ジメチル-n-ブトキシ基、1,3-ジメチル-n-ブトキシ基、2,2-ジメチル-n-ブトキシ基、2,3-ジメチル-n-ブトキシ基、3,3-ジメチル-n-ブトキシ基、1-エチル-n-ブトキシ基、2-エチル-n-ブトキシ基、1,1,2-トリメチル-n-プロポキシ基、1,2,2-トリメチル-n-プロポキシ基、1-エチル-1-メチル-n-プロポキシ基、1-エチル-2-メチル-n-プロポキシ基等が挙げられる。
アリール基の具体例としては、フェニル基、o-クロルフェニル基、m-クロルフェニル基、p-クロルフェニル基、o-フルオロフェニル基、p-フルオロフェニル基、o-メトキシフェニル基、p-メトキシフェニル基、p-ニトロフェニル基、p-シアノフェニル基、α-ナフチル基、β-ナフチル基、o-ビフェニリル基、m-ビフェニリル基、p-ビフェニリル基、1-アントリル基、2-アントリル基、9-アントリル基、1-フェナントリル基、2-フェナントリル基、3-フェナントリル基、4-フェナントリル基、9-フェナントリル基等が挙げられる。
その具体例としては、ベンジル基、p-メチルフェニルメチル基、m-メチルフェニルメチル基、o-エチルフェニルメチル基、m-エチルフェニルメチル基、p-エチルフェニルメチル基、2-プロピルフェニルメチル基、4-イソプロピルフェニルメチル基、4-イソブチルフェニルメチル基、α-ナフチルメチル基等が挙げられる。
これらアルキル基、アルコキシ基としては上記と同様のものが挙げられる。
ハロゲン原子としては、フッ素原子、塩素原子、臭素原子、ヨウ素原子が挙げられる。
これらハロゲン原子、アルキル基、アルコキシ基としては上記と同様のものが挙げられる。
炭素数1~10の分岐構造を有していてもよいアルキレン基としては、メチレン基、エチレン基、プロピレン基、トリメチレン基、テトラメチレン基、ペンタメチレン基等が挙げられる。
また、W1等のベンゼン環の連結基としては、高い水素結合能を有する、カルボニルを含む基やアミン等の官能基が、アミン部位の水素原子(R、R’、R”および/またはR'''が水素原子の場合)と水素結合を形成してよりアリール部分が密に集まり易く、電子密度が向上するため好適である。
以上のような観点から、下記式で示されるアリール基が好ましい。
上記のような置換基の特性や、その入手容易性等を考慮すると、本発明における好適なAr1およびAr2の組み合わせとしては、下記式(20)~(24)から選ばれる2種が挙げられる。
本発明における、好適な繰り返し単位構造としては、以下の式(25)~(27)で示されるものが挙げられるが、これらに限定されるものではない。
なお、本発明における重量平均分子量は、ゲルパーミエーションクロマトグラフィー(以下、GPCという)分析による標準ポリスチレン換算で得られる平均分子量である。
本発明の共重合型のトリアジン環含有重合体は、ハロゲン化シアヌルと、少なくとも2種類のジアミノアリール化合物とを反応させて得ることができ、例えば、下記スキーム1に示されるように、繰り返し構造(25’)を有するハイパーブランチポリマーは、ハロゲン化シアヌル(28)、ビスアミノフェニルフルオレン化合物(29)およびm-フェニレンジアミン化合物(30)を適当な有機溶媒中で反応させて得ることができる。
種々の分子量のトリアジン環末端を有する高分岐重合体(ハイパーブランチポリマー)を得るために、ハロゲン化シアヌル(28)2当量に対して、m-フェニレンジアミン化合物(30)およびビスアミノフェニルフルオレン化合物(29)の総量として、3当量未満の量で用いることが好ましい。
一方、種々の分子量のアミン末端を有する高分岐重合体(ハイパーブランチポリマー)を得るために、m-フェニレンジアミン化合物(30)およびビスアミノフェニルフルオレン化合物(29)の総量3当量に対して、ハロゲン化シアヌル(28)2当量未満の量で用いることが好ましい。
このように、m-フェニレンジアミン化合物(30)およびビスアミノフェニルフルオレン化合物(29)やハロゲン化シアヌル(28)の量を適宜調節することで、得られる高分岐重合体(ハイパーブランチポリマー)の分子量を容易に調節することができる。
また、スキーム2の方法の場合、各原料の仕込み量としては、目的とするハイパーブランチポリマーが得られる限りにおいて任意であるが、ハロゲン化シアヌル(28)1当量に対し、ジアミノ化合物(29),(30)それぞれ0.01~10当量が好ましい。
中でもN,N-ジメチルホルムアミド、ジメチルスルホキシド、N-メチル-2-ピロリドン、N,N-ジメチルアセトアミド、およびそれらの混合溶媒が好ましく、特に、N,N-ジメチルアセトアミド、N-メチル-2-ピロリドンが好適である。
特にスキーム1の反応では、リニア性を抑え、分岐度を高めるという点から、反応温度は60~150℃が好ましく、80~150℃が好ましく、80~120℃が好ましい。
スキーム2の第1段階(化合物(31)および(32)の合成段階)の方法において、反応温度は、用いる溶媒の融点から溶媒の沸点までの範囲で適宜設定すればよいが、特に、-50~50℃程度が好ましく、-20~50℃程度がより好ましく、-10~50℃程度がより一層好ましく、-10~10℃がさらに好ましい。
特にスキーム2の方法では、第1段階の反応にて、-50~50℃で反応させる第1工程と、この工程に続いて60~150℃で反応させる第2工程とからなる2段階工程を採用することが好ましい。
この場合、予め溶媒に溶かしておく成分および後から加える成分はどちらでもよいが、ジアミノ化合物(29),(30)の加熱溶液中に、ハロゲン化シアヌル(28)を添加する手法が好ましい。
また、スキーム2の反応において、予め溶媒に溶かしておく成分および後から加える成分はどちらでもよいが、ハロゲン化シアヌル(28)の冷却溶液中に、ジアミノ化合物(29),(30)を添加する手法が好ましい。
後から加える成分は、ニートで加えても、上述したような有機溶媒に溶かした溶液で加えてもよいが、操作の容易さや反応のコントロールのし易さなどを考慮すると、後者の手法が好適である。
また、添加は、滴下等によって徐々に加えても、全量一括して加えてもよい。
スキーム1において、加熱した状態で両化合物を混合した後は、(段階的に温度を上げることなく)一段階で反応させた場合でも、ゲル化することなく、目的とする共重合型のトリアジン環含有ハイパーブランチポリマーを得ることができる。
この塩基の具体例としては、炭酸カリウム、水酸化カリウム、炭酸ナトリウム、水酸化ナトリウム、炭酸水素ナトリウム、ナトリウムエトキシド、酢酸ナトリウム、炭酸リチウム、水酸化リチウム、酸化リチウム、酢酸カリウム、酸化マグネシウム、酸化カルシウム、水酸化バリウム、リン酸三リチウム、リン酸三ナトリウム、リン酸三カリウム、フッ化セシウム、酸化アルミニウム、アンモニア、トリメチルアミン、トリエチルアミン、ジイソプロピルメチルアミン、ジイソプロピルエチルアミン、N-メチルピペリジン、2,2,6,6-テトラメチル-N-メチルピペリジン、ピリジン、4-ジメチルアミノピリジン、N-メチルモルホリン等が挙げられる。
塩基の添加量は、ハロゲン化シアヌル(28)1当量に対して1~100当量が好ましく、1~10当量がより好ましい。なお、これらの塩基は水溶液にして用いてもよい。
得られるポリマーには、原料成分が残存していないことが好ましいが、本発明の効果を損なわなければ一部の原料が残存していてもよい。
いずれのスキームの方法においても、反応終了後、生成物は再沈法等によって容易に精製できる。
これらの中でも、アルキルアミノ基、アルコキシシリル基含有アルキルアミノ基、アラルキルアミノ基、アリールアミノ基が好ましく、アルキルアミノ基、アリールアミノ基がより好ましく、アリールアミノ基がさらに好ましい。
アルキルアミノ基の具体例としては、メチルアミノ基、エチルアミノ基、n-プロピルアミノ基、イソプロピルアミノ基、n-ブチルアミノ基、イソブチルアミノ基、s-ブチルアミノ基、t-ブチルアミノ基、n-ペンチルアミノ基、1-メチル-n-ブチルアミノ基、2-メチル-n-ブチルアミノ基、3-メチル-n-ブチルアミノ基、1,1-ジメチル-n-プロピルアミノ基、1,2-ジメチル-n-プロピルアミノ基、2,2-ジメチル-n-プロピルアミノ基、1-エチル-n-プロピルアミノ基、n-ヘキシルアミノ基、1-メチル-n-ペンチルアミノ基、2-メチル-n-ペンチルアミノ基、3-メチル-n-ペンチルアミノ基、4-メチル-n-ペンチルアミノ基、1,1-ジメチル-n-ブチルアミノ基、1,2-ジメチル-n-ブチルアミノ基、1,3-ジメチル-n-ブチルアミノ基、2,2-ジメチル-n-ブチルアミノ基、2,3-ジメチル-n-ブチルアミノ基、3,3-ジメチル-n-ブチルアミノ基、1-エチル-n-ブチルアミノ基、2-エチル-n-ブチルアミノ基、1,1,2-トリメチル-n-プロピルアミノ基、1,2,2-トリメチル-n-プロピルアミノ基、1-エチル-1-メチル-n-プロピルアミノ基、1-エチル-2-メチル-n-プロピルアミノ基等が挙げられる。
アリールアミノ基の具体例としては、フェニルアミノ基、メトキシカルボニルフェニルアミノ基、エトキシカルボニルフェニルアミノ基、ナフチルアミノ基、メトキシカルボニルナフチルアミノ基、エトキシカルボニルナフチルアミノ基、アントラニルアミノ基、ピレニルアミノ基、ビフェニルアミノ基、ターフェニルアミノ基、フルオレニルアミノ基等が挙げられる。
アラルキルオキシ基の具体例としては、ベンジルオキシ基、p-メチルフェニルメチルオキシ基、m-メチルフェニルメチルオキシ基、o-エチルフェニルメチルオキシ基、m-エチルフェニルメチルオキシ基、p-エチルフェニルメチルオキシ基、2-プロピルフェニルメチルオキシ基、4-イソプロピルフェニルメチルオキシ基、4-イソブチルフェニルメチルオキシ基、α-ナフチルメチルオキシ基等が挙げられる。
その他、アルキル基、アラルキル基、アリール基としては上述した基と同様のものが挙げられる。
これらの基は、トリアジン環上のハロゲン原子を対応する置換基を与える化合物で置換することで容易に導入することができ、例えば、下記式スキーム3に示されるように、アニリン誘導体を加えて反応させることで、少なくとも1つの末端にフェニルアミノ基を有するハイパーブランチポリマー(33)が得られる。
この手法によって得られたハイパーブランチポリマーは、溶剤への溶解性(凝集抑制)や、架橋剤との架橋性に優れたものとなるため、後述する架橋剤と組み合わせた組成物として用いる場合に特に有利である。
ここで、有機モノアミンとしては、アルキルモノアミン、アラルキルモノアミン、アリールモノアミンのいずれを用いることもできる。
アリールモノアミンの具体例としては、アニリン、p-メトキシカルボニルアニリン、p-エトキシカルボニルアニリン、p-メトキシアニリン、1-ナフチルアミン、2-ナフチルアミン、アントラニルアミン、1-アミノピレン、4-ビフェニリルアミン、o-フェニルアニリン、4-アミノ-p-ターフェニル、2-アミノフルオレン等が挙げられる。
この場合の反応温度も、リニア性を抑え、分岐度を高めるという点から、60~150℃が好ましく、80~150℃が好ましく、80~120℃が好ましい。
ただし、有機モノアミン、ハロゲン化シアヌル化合物、ジアミノアリール化合物の3成分の混合は、低温下で行ってもよく、その場合の温度としては、-50~50℃程度が好ましく、-20~50℃程度がより好ましく、-20~10℃がさらに好ましい。低温仕込み後は、重合させる温度まで一気に(一段階で)昇温して反応を行うことが好ましい。
また、ハロゲン化シアヌル化合物とジアミノアリール化合物の2成分の混合を低温下で行ってもよく、その場合の温度としては、-50~50℃程度が好ましく、-20~50℃程度がより好ましく、-20~10℃がさらに好ましい。低温仕込み後、有機モノアミンを加え、重合させる温度まで一気に(一段階で)昇温して反応を行うことが好ましい。
また、このような有機モノアミンの存在下で、ハロゲン化シアヌル化合物と、ジアミノアリール化合物とを反応させる反応は、上述と同様の有機溶媒を用いて行ってもよい。
これらの組成物は、膜形成用組成物として用いることができ、各種の溶剤に溶かした膜形成用組成物(ポリマーワニスともいう)として好適に使用できる。
重合体を溶解するのに用いる溶剤は、重合時に用いた溶媒と同じものでも別のものでもよい。この溶剤は、重合体との相溶性を損なわなければ特に限定されず、1種でも複数種でも任意に選択して用いることができる。
このような溶剤の具体例としては、トルエン、p-キシレン、o-キシレン、m-キシレン、エチルベンゼン、スチレン、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、エチ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、プロピ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エチルエーテル、エチレングリコールモノイソプロピルエーテル、エチレングリコールメチルエーテルアセテート、プロピレングリコールモノメチルエーテルアセテート、エチレングリコールエチルエーテルアセテート、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ブチルエーテル、エチレングリコ-ルモノブチルエーテル、ジエチレングリコールジエチルエーテル、ジプロピレングリコールモノメチルエーテル、ジエチレングリコールモノメチルエーテル、ジプロピ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モノエチルエーテル、トリエチレングリコールジメチルエーテル、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコール、1-オクタノール、エチレングリコール、ヘキシレングリコール、トリメチレングリコール、1-メトキシ-2-ブタノール、シクロヘキサノール、ジアセトンアルコール、フルフリルアルコール、テトラヒドロフルフリルアルコール、プロピレングリコール、ベンジルアルコール、1,3-ブタンジオール、1,4-ブタンジオール、2,3-ブタンジオール、γ-ブチロラクトン、アセトン、メチルエチルケトン、メチルイソプロピルケトン、ジエチルケトン、メチルイソブチルケトン、メチルノーマルブチルケトン、シクロヘキサノン、酢酸エチル、酢酸イソプロピル、酢酸ノーマルプロピル、酢酸イソブチル、酢酸ノーマルブチル、乳酸エチル、メタノール、エタノール、イソプロパノール、tert-ブタノール、アリルアルコール、ノーマルプロパノール、2-メチル-2-ブタノール、イソブタノール、ノーマルブタノール、2-メチル-1-ブタノール、1-ペンタノール、2-メチル-1-ペンタノール、2-エチルヘキサノール、1-メトキシ-2-プロパノール、テトラヒドロフラン、1,4-ジオキサン、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン、1,3-ジメチル-2-イミダゾリジノン、ジメチルスルホキシド、N-シクロヘキシル-2-ピロリジノン等が挙げられ、これらは単独で用いても、2種以上混合して用いてもよい。
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セチルエーテル、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類;ポリオキシエチレンオクチルフェノールエーテル、ポリオキシエチレンノニルフェノールエーテル等のポリオキシエチレンアルキルアリルエーテル類;ポリオキシエチレン・ポリオキシプロピレンブロックコポリマー類;ソルビタンモノラウレート、ソルビタンモノパルミテート、ソルビタンモノステアレート、ソルビタンモノオレエート、ソルビタントリオレエート、ソルビタントリステアレート等のソルビタン脂肪酸エステル類;ポリオキシエチレンソルビタンモノラウレート、ポリオキシエチレンソルビタンモノパルミテート、ポリオキシエチレンソルビタンモノステアレート、ポリオキシエチレンソルビタントリオレエート、ポリオキシエチレンソルビタントリステアレート等のポリオキシエチレンソルビタン脂肪酸エステル類等のノニオン系界面活性剤、商品名エフトップEF301、EF303、EF352(三菱マテリアル電子化成(株)製(旧(株)ジェムコ製)、商品名メガファックF171、F173、R-08、R-30、F-553、F-554(DIC(株)製)、フロラードFC430、FC431(住友スリーエム(株)製)、商品名アサヒガードAG710,サーフロンS-382、SC101、SC102、SC103、SC104、SC105、SC106(旭硝子(株)製)等のフッ素系界面活性剤、オルガノシロキサンポリマーKP341(信越化学工業(株)製)、BYK-302、BYK-307、BYK-322、BYK-323、BYK-330、BYK-333、BYK-370、BYK-375、BYK-378(ビックケミー・ジャパン(株)製)等が挙げられる。
そのような化合物としては、メチロール基、メトキシメチル基などの架橋形成置換基を有するメラミン系化合物、置換尿素系化合物、エポキシ基またはオキセタン基などの架橋形成置換基を含有する化合物、ブロック化イソシアナートを含有する化合物、酸無水物を有する化合物、(メタ)アクリル基を有する化合物、フェノプラスト化合物等が挙げられるが、耐熱性や保存安定性の観点からエポキシ基、ブロックイソシアネート基、(メタ)アクリル基を含有する化合物が好ましい。
また、ブロックイソシアネート基は、尿素結合で架橋し、カルボニル基を有するため屈折率が低下しないという点からも好ましい。
なお、これらの化合物は、ポリマーの末端処理に用いる場合は少なくとも1個の架橋形成置換基を有していればよく、ポリマー同士の架橋処理に用いる場合は少なくとも2個の架橋形成置換基を有する必要がある。
架橋剤の具体例としては、トリス(2,3-エポキシプロピル)イソシアヌレート、1,4-ブタンジオールジグリシジルエーテル、1,2-エポキシ-4-(エポキシエチル)シクロヘキサン、グリセロールトリグリシジルエーテル、ジエチレングリコールジグリシジルエーテル、2,6-ジグリシジルフェニルグリシジルエーテル、1,1,3-トリス[p-(2,3-エポキシプロポキシ)フェニル]プロパン、1,2-シクロヘキサンジカルボン酸ジグリシジルエステル、4,4’-メチレンビス(N,N-ジグリシジルアニリン)、3,4-エポキシシクロヘキシルメチル-3,4-エポキシシクロヘキサンカルボキシレート、トリメチロールエタントリグリシジルエーテル、ビスフェノール-A-ジグリシジルエーテル、ペンタエリスリトールポリグリシジルエーテル等が挙げられる。
また、酸無水物化合物の具体例としては、無水フタル酸、テトラヒドロ無水フタル酸、ヘキサヒドロ無水フタル酸、メチルテトラヒドロ無水フタル酸、メチルヘキサヒドロ無水フタル酸、無水ナジック酸、無水メチルナジック酸、無水マレイン酸、無水コハク酸、オクチル無水コハク酸、ドデセニル無水コハク酸等の分子内に1個の酸無水物基を有するもの;1,2,3,4-シクロブタンテトラカルボン酸二無水物、ピロメリット酸無水物、3,4-ジカルボキシ-1,2,3,4-テトラヒドロ-1-ナフタレンコハク酸二無水物、ビシクロ[3.3.0]オクタン-2,4,6,8-テトラカルボン酸二無水物、5-(2,5-ジオキソテトラヒドロ-3-フラニル)-3-メチル-3-シクロヘキセン-1,2-ジカルボン酸無水物、1,2,3,4-ブタンテトラカルボン酸二無水物、3,3’,4,4’-ベンゾフェノンテトラカルボン酸二無水物、3,3’,4,4’-ビフェニルテトラカルボン酸二無水物、2,2-ビス(3,4-ジカルボキシフェニル)ヘキサフルオロプロパン二無水物、1,3-ジメチル-1,2,3,4-シクロブタンテトラカルボン酸二無水物等の分子内に2個の酸無水物基を有するもの等が挙げられる。
(メタ)アクリル基を有する化合物としては、例えば、エチレングリコールジアクリレート、エチレングリコールジメタクリレート、ポリエチレングリコールジアクリレート、ポリエチレングリコールジメタクリレート、エトキシ化ビスフェノールAジアクリレート、エトキシ化ビスフェノールAジメタクリレート、エトキシ化トリメチロールプロパントリアクリレート、エトキシ化トリメチロールプロパントリメタクリレート、エトキシ化グリセリントリアクリレート、エトキシ化グリセリントリメタクリレート、エトキシ化ペンタエリスリトールテトラアクリレート、エトキシ化ペンタエリスリトールテトラメタクリレート、エトキシ化ジペンタエリスリトールヘキサアクリレート、ポリグリセリンモノエチレンオキサイドポリアクリレート、ポリグリセリンポリエチレングリコールポリアクリレート、ジペンタエリスリトールヘキサアクリレート、ジペンタエリスリトールヘキサメタクリレート、ネオペンチルグリコールジアクリレート、ネオペンチルグリコールジメタクリレート、ペンタエリスリトールトリアクリレート、ペンタエリスリトールトリメタクリレート、トリメチロールプロパントリアクリレート、トリメチロールプロパントリメタクリレート、トリシクロデカンジメタノールジアクリレート、トリシクロデカンジメタノールジメタクリレート、1,6-ヘキサンジオールジアクリレート、1,6-ヘキサンジオールジメタクリレート等が挙げられる。
一分子中2個以上のイソシアネート基を有する化合物としては、例えば、イソホロンジイソシアネート、1,6-ヘキサメチレンジイソシアネート、メチレンビス(4-シクロヘキシルイソシアネート)、トリメチルヘキサメチレンジイソシアネートのポリイソシアネートや、これらの二量体、三量体、および、これらとジオール類、トリオール類、ジアミン類、またはトリアミン類との反応物などが挙げられる。
ブロック剤としては、例えば、メタノール、エタノール、イソプロパノール、n-ブタノール、2-エトキシヘキサノール、2-N,N-ジメチルアミノエタノール、2-エトキシエタノール、シクロヘキサノール等のアルコール類;フェノール、o-ニトロフェノール、p-クロロフェノール、o-、m-またはp-クレゾール等のフェノール類;ε-カプロラクタム等のラクタム類、アセトンオキシム、メチルエチルケトンオキシム、メチルイソブチルケトンオキシム、シクロヘキサノンオキシム、アセトフェノンオキシム、ベンゾフェノンオキシム等のオキシム類;ピラゾール、3,5-ジメチルピラゾール、3-メチルピラゾール等のピラゾール類;ドデカンチオール、ベンゼンチオール等のチオール類などが挙げられる。
メラミン系化合物としては、例えば、ヘキサメトキシメチルメラミン CYMEL(登録商標)303、テトラブトキシメチルグリコールウリル 同1170、テトラメトキシメチルベンゾグアナミン 同1123(以上、日本サイテックインダストリーズ(株)製)等のサイメルシリーズ、メチル化メラミン樹脂であるニカラック(登録商標)MW-30HM、同MW-390、同MW-100LM、同MX-750LM、メチル化尿素樹脂である同MX-270、同MX-280、同MX-290(以上、(株)三和ケミカル製)等のニカラックシリーズ等が挙げられる。
オキセタン化合物としては、オキセタニル基を一分子中2個以上有し、そして熱硬化時の高温に曝されると、本発明のトリアジン環含有重合体との間で付加反応により架橋反応が進行するものである。
オキセタン基を有する化合物としては、例えば、オキセタン基を含有するOXT-221、OX-SQ-H、OX-SC(以上、東亜合成(株)製)等が挙げられる。
フェノプラスト化合物としては、例えば、2,6-ジヒドロキシメチル-4-メチルフェノール、2,4-ジヒドロキシメチル-6-メチルフェノール、ビス(2-ヒドロキシ-3-ヒドロキシメチル-5-メチルフェニル)メタン、ビス(4-ヒドロキシ-3-ヒドロキシメチル-5-メチルフェニル)メタン、2,2-ビス(4-ヒドロキシ-3,5-ジヒドロキシメチルフェニル)プロパン、ビス(3-ホルミル-4-ヒドロキシフェニル)メタン、ビス(4-ヒドロキシ-2,5-ジメチルフェニル)ホルミルメタン、α,α-ビス(4-ヒドロキシ-2,5-ジメチルフェニル)-4-ホルミルトルエン等が挙げられる。
フェノプラスト化合物は、市販品としても入手が可能であり、その具体例としては、26DMPC、46DMOC、DM-BIPC-F、DM-BIOC-F、TM-BIP-A、BISA-F、BI25X-DF、BI25X-TPA(以上、旭有機材工業(株)製)等が挙げられる。
架橋剤を用いることで、架橋剤とトリアジン環含有重合体が有する反応性の末端置換基とが反応し、膜密度の向上、耐熱性の向上、熱緩和能力の向上などの効果を発現できる場合がある。
なお、上記その他の成分は、本発明の組成物を調製する際の任意の工程で添加することができる。
組成物の塗布方法は任意であり、例えば、スピンコート法、ディップ法、フローコート法、インクジェット法、スプレー法、バーコート法、グラビアコート法、スリットコート法、ロールコート法、転写印刷法、刷毛塗り、ブレードコート法、エアーナイフコート法等の方法を採用できる。
焼成温度は、溶媒を蒸発させる目的では特に限定されず、例えば40~400℃で行うことができる。これらの場合、より高い均一製膜性を発現させたり、基材上で反応を進行させたりする目的で2段階以上の温度変化をつけてもよい。
焼成方法としては、特に限定されるものではなく、例えば、ホットプレートやオーブンを用いて、大気、窒素等の不活性ガス、真空中等の適切な雰囲気下で蒸発させればよい。
焼成温度および焼成時間は、目的とする電子デバイスのプロセス工程に適合した条件を選択すればよく、得られる膜の物性値が電子デバイスの要求特性に適合するような焼成条件を選択すればよい。
樹脂の具体例としては、特に限定されるものではない。熱可塑性樹脂としては、例えば、PE(ポリエチレン)、PP(ポリプロピレン)、EVA(エチレン-酢酸ビニル共重合体)、EEA(エチレン-アクリル酸エチル共重合体)等のポリオレフィン系樹脂;PS(ポリスチレン)、HIPS(ハイインパクトポリスチレン)、AS(アクリロニトリル-スチレン共重合体)、ABS(アクリロニトリル-ブタジエン-スチレン共重合体)、MS(メタクリル酸メチル-スチレン共重合体)等のポリスチレン系樹脂;ポリカーボネート樹脂;塩化ビニル樹脂;ポリアミド樹脂;ポリイミド樹脂;PMMA(ポリメチルメタクリレート)等の(メタ)アクリル樹脂;PET(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、ポリエチレンナフタレート、ポリブチレンナフタレート、PLA(ポリ乳酸)、ポリ-3-ヒドロキシ酪酸、ポリカプロラクトン、ポリブチレンサクシネート、ポリエチレンサクシネート/アジペート等のポリエステル樹脂;ポリフェニレンエーテル樹脂;変性ポリフェニレンエーテル樹脂;ポリアセタール樹脂;ポリスルホン樹脂;ポリフェニレンサルファイド樹脂;ポリビニルアルコール樹脂;ポリグルコール酸;変性でんぷん;酢酸セルロース、三酢酸セルロース;キチン、キトサン;リグニンなどが挙げられ、熱硬化性樹脂としては、例えば、フェノール樹脂、尿素樹脂、メラミン樹脂、不飽和ポリエステル樹脂、ポリウレタン樹脂、エポキシ樹脂などが挙げられる。
これらの樹脂は、単独で用いても、2種以上組み合わせて用いてもよく、その使用量は、上記トリアジン環含有重合体100質量部に対して、1~10,000質量部が好ましく、より好ましくは1~1,000質量部である。
(メタ)アクリレート化合物の例としては、メチル(メタ)アクリレート、エチル(メタ)アクリレート、エチレングリコールジ(メタ)アクリレート、テトラエチレングリコールジ(メタ)アクリレート、ポリエチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、ポリプロピレングリコールジ(メタ)アクリレート、1,4-ブタンジオールジ(メタ)アクリレート、1,6-ヘキサンジオールジ(メタ)アクリレート、ネオペンチルグリコールジ(メタ)アクリレート、トリメチロールプロパントリオキシエチル(メタ)アクリレート、トリシクロデカンジメタノールジ(メタ)アクリレート、トリシクロデカニルジ(メタ)アクリレート、トリメチロールプロパントリオキシプロピル(メタ)アクリレート、トリス-2-ヒドロキシエチルイソシアヌレートトリ(メタ)アクリレート、トリス-2-ヒドロキシエチルイソシアヌレートジ(メタ)アクリレート、1,9-ノナンジオールジ(メタ)アクリレート、ペンタエリスリトールジ(メタ)アクリレート、グリセリンメタクリレートアクリレート、ペンタエリスリトールトリ(メタ)アクリレート、トリメチロールプロパントリメタクリレート、(メタ)アクリル酸アリル、(メタ)アクリル酸ビニル、エポキシ(メタ)アクリレート、ポリエステル(メタ)アクリレート、ウレタン(メタ)アクリレート等が挙げられる。
光ラジカル重合開始剤としては、例えば、アセトフェノン類、ベンゾフェノン類、ミヒラーのベンゾイルベンゾエート、アミロキシムエステル、テトラメチルチウラムモノサルファイドおよびチオキサントン類等が挙げられる。
特に、光開裂型の光ラジカル重合開始剤が好ましい。光開裂型の光ラジカル重合開始剤については、最新UV硬化技術(159頁、発行人:高薄一弘、発行所:(株)技術情報協会、1991年発行)に記載されている。
市販の光ラジカル重合開始剤としては、例えば、チバ・ジャパン(株)製 商品名: イルガキュア 184、369、651、500、819、907、784、2959、CGI1700、CGI1750、CGI1850、CG24-61、ダロキュア 1116、1173、BASF社製 商品名:ルシリン TPO、UCB社製 商品名:ユベクリル P36、フラテツリ・ランベルティ社製 商品名:エザキュアー KIP150、KIP65LT、KIP100F、KT37、KT55、KTO46、KIP75/B等が挙げられる。
重合に用いる溶剤は、上記膜形成用組成物で例示した溶剤と同様のものが挙げられる。
[1H-NMR]
装置:Varian NMR System 400NB(400MHz)
JEOL-ECA700(700MHz)
測定溶媒:DMSO-d6
基準物質:テトラメチルシラン(TMS)(δ0.0ppm)
[GPC]
(1)テトラヒドロフラン(THF)系
装置:東ソー(株)製 HLC-8200 GPC
カラム:Shodex KF-802.5L+KF-803L
カラム温度:40℃
溶媒:THF
検出器:UV(254nm)
検量線:標準ポリスチレン
(2)ジメチルホルムアミド(DMF)系
装置:東ソー(株)製 HLC-8200 GPC
カラム:Shodex OHpak SB-803HQ+SB-804HQ
カラム温度:40℃
溶媒:DMF
検出器:UV(254nm)
検量線:標準ポリスチレン
(3)N-メチルピロリドン(NMP系)
装置:SHIMADZU SPD-10A VP
カラム:SHODEX K‐804L,K‐805L
カラム温度:60℃
溶媒:NMP
検出器:UV(254nm)
検量線:標準ポリスチレン
[エリプソメーター]
装置:ジェー・エー・ウーラム・ジャパン製 多入射角分光エリプソメーターVASE
[示差熱天秤(TG-DTA)]
装置:(株)リガク製 TG-8120
昇温速度:10℃/分
測定温度:25℃-750℃
[DSC]
装置:NETZSCH DSC204 F1 Phenix
昇温速度:40K/min
室温まで放冷後、トリエチルアミン(91.07g、0.90mol)を加え、副生した塩化水素を除去し、生成した塩酸塩をろ過した。ろ液を28%アンモニア水溶液(182.14g)とイオン交換水3367gとの混合溶液に再沈殿させた。沈殿物をろ過し、THF422gに再溶解させ、イオン交換水3000gとメタノール100gの混合溶液中に再沈殿した。得られた沈殿物をろ過し、減圧乾燥機で150℃、8時間乾燥し、目的とする高分子化合物[4](以下、HB-TDFA03と略す)73.33gを得た。
HB-TDFA03の1H-NMRスペクトルの測定結果を図1に示す。得られたHB-TDFA03は式(1)で表される構造単位を有する化合物である。HB-TDFA03のGPC(THF系)によるポリスチレン換算で測定される重量平均分子量Mwは5,400、多分散度Mw/Mnは4.05であった。
実施例1で得られたHB-TDFA03 5.73mgを白金パンに加え、TG-DTAにより昇温速度15℃/minで測定を行った。その結果を図2に示す。5%重量減少は408℃であった。また、DSC測定によりガラス転移温度を測定したところ、227℃に転移点が観測された。
実施例1で得られたHB-TDFA03(0.1g)を、シクロヘキサノン0.9gに溶解し、薄黄色透明溶液を得た。得られたポリマーワニスをガラス基板上にスピンコーターを用いて200rpmで5秒間、2000rpmで30秒間スピンコートし、100℃で1分、300℃で5分間加熱して溶媒を除去し、被膜を得た。得られた被膜の屈折率を測定したところ、550nmにおける屈折率は、1.772であった。
仕込み量を、2,4,6-トリクロロ-1,3,5-トリアジン[1](33.19g,0.18mol,エボニック・デグサ社製)、m-フェニレンジアミン[2](23.85g、0.22mol)、ビスアミノフェニルフルオレン[3](8.55g、0.024mol)およびアニリン(5.7g、0.06mol)とした以外は、実施例1と同様に反応を行い、目的とする高分子化合物[4](以下、HB-TDFA10と略す)57.19gを得た。
HB-TDFA10の1H-NMRスペクトルの測定結果を図3に示す。得られたHB-TDFA10は式(1)で表される構造単位を有する化合物である。HB-TDFA10のGPC(THF系)によるポリスチレン換算で測定される重量平均分子量Mwは6,200、多分散度Mw/Mnは4.53であった。
実施例2と同様にして、実施例4で得られたHB-TDFA10のTG-DTA測定を行ったところ、5%重量減少は414℃であった。その結果を図4に示す。
実施例4で得られたHB-TDFA10(0.1g)を、シクロヘキサノン0.9gに溶解し、薄黄色透明溶液を得た。得られたポリマーワニスをガラス基板上にスピンコーターを用いて200rpmで5秒間、2000rpmで30秒間スピンコートし、100℃で1分、300℃で5分間加熱して溶媒を除去し、被膜を得た。得られた被膜の屈折率を測定したところ、550nmにおける屈折率は、1.764であった。
仕込み量を、2,4,6-トリクロロ-1,3,5-トリアジン[1](3.38g,0.018mol,エボニック・デグサ社製)、m-フェニレンジアミン[2](1.70g、0.015mol)、ビスアミノフェニルフルオレン[3](2.37g、0.007mol)およびアニリン(0.57g、0.06mol)とした以外は、実施例1と同様に反応を行い、目的とする高分子化合物[4](以下、HB-TDFA30と略す)5.79gを得た。
HB-TDFA30の1H-NMRスペクトルの測定結果を図5に示す。得られたHB-TDFA30は式(1)で表される構造単位を有する化合物である。HB-TDFA30のGPC(THF系)によるポリスチレン換算で測定される重量平均分子量Mwは5,800、多分散度Mw/Mnは2.78であった。
実施例2と同様にして、実施例7で得られたHB-TDFA30のTG-DTA測定を行ったところ、5%重量減少は423℃であった。その結果を図6に示す。
実施例7で得られたHB-TDFA30(0.1g)を、シクロヘキサノン0.9gに溶解し、薄黄色透明溶液を得た。得られたポリマーワニスをガラス基板上にスピンコーターを用いて200rpmで5秒間、2000rpmで30秒間スピンコートし、100℃で1分、300℃で5分間加熱して溶媒を除去し、被膜を得た。得られた被膜の屈折率を測定したところ、550nmにおける屈折率は、1.762であった。
仕込み量を、2,4,6-トリクロロ-1,3,5-トリアジン[1](3.33g,0.018mol,エボニック・デグサ社製)、m-フェニレンジアミン[2](1.23g、0.011mol)、ビスアミノフェニルフルオレン[3](3.92g、0.011mol)およびアニリン(0.59g、0.06mol)とした以外は、実施例1と同様に反応を行い、目的とする高分子化合物[4](以下、HB-TDFA50と略す)6.65gを得た。
HB-TDFA50の1H-NMRスペクトルの測定結果を図7に示す。得られたHB-TDFA50は式(1)で表される構造単位を有する化合物である。HB-TDFA50のGPC(THF系)によるポリスチレン換算で測定される重量平均分子量Mwは6,400、多分散度Mw/Mnは2.80であった。
実施例2と同様にして、実施例10で得られたHB-TDFA50のTG-DTA測定を行ったところ、5%重量減少は465℃であった。その結果を図8に示す。
実施例10で得られたHB-TDFA50(0.1g)を、シクロヘキサノン0.9gに溶解し、薄黄色透明溶液を得た。得られたポリマーワニスをガラス基板上にスピンコーターを用いて200rpmで5秒間、2000rpmで30秒間スピンコートし、100℃で1分、300℃で5分間加熱して溶媒を除去し、被膜を得た。得られた被膜の屈折率を測定したところ、550nmにおける屈折率は、1.750であった。
実施例10で得られたHB-TDFA50を、架橋剤であるジペンタエリスリトール ヘキサアクリレート(日本化薬(株)製)に対し、10、30、50、70質量%添加し、固形分10質量%のシクロヘキサノン溶液を調製し、ガラス基板に200rpm、5秒、1500rpm、30秒でスピンコートを行った。その後、100℃で1分、250℃で5分焼成を行い、溶媒を除去した。得られた各塗膜について屈折率、膜厚を測定した。その結果を表1に示す。
実施例13で作製した塗膜を、シクロヘキサノンに浸し、5分後、スプレードライを行い、実施例13と同様に屈折率、膜厚の測定を行った。その結果を表1に併せて示す。
実施例10で得られたHB-TDFA50を、架橋剤であるタケネートB882N(三井化学(株)製)に対して10、30、50、70質量%添加し、固形分10質量%のシクロヘキサノン溶液を調製し、ガラス基板に200rpm、5秒、1500rpm、30秒でスピンコートを行った。その後、100℃で1分、250℃で5分焼成を行い、溶媒を除去した。得られた塗膜について屈折率、膜厚を測定した。その結果を表2に示す。
実施例15で作製した塗膜をシクロヘキサノンに浸し、5分後、スプレードライを行い、実施例15と同様に屈折率、膜厚の測定を行った。その結果を表2に併せて示す。
HB-TAM-mDAの1H-NMRスペクトルの測定結果を図9に示す。得られたHB-TAM-mDAは式(1)で表される構造単位を有する化合物である。HB-TAM-mDAのGPC(DMF系)によるポリスチレン換算で測定される重量平均分子量Mwは185,000、多分散度Mw/Mnは39.2であった。
実施例2と同様にして、実施例17で得られたHB-TAM-mDAのTG-DTA測定を行ったところ、5%重量減少は417℃であった。その結果を図10に示す。
実施例17で得られたHB-TAM-mDA(0.1g)を、シクロヘキサノン0.9gに溶解し、薄黄色透明溶液を得た。得られたポリマーワニスをガラス基板上にスピンコーターを用いて200rpmで5秒間、2000rpmで30秒間スピンコートし、100℃で1分、300℃で5分間加熱して溶媒を除去し、被膜を得た。得られた被膜の屈折率を測定したところ、550nmにおける屈折率は、1.843であった。
HB-TAM-FAの1H-NMRスペクトルの測定結果を図11に示す。得られたHB-TAM-mDAは式(1)で表される構造単位を有する化合物である。HB-TAM-FAのGPC(DMF系)によるポリスチレン換算で測定される重量平均分子量Mwは183,000、多分散度Mw/Mnは55.9であった。
実施例2と同様にして、実施例20で得られたHB-TAM-FAのTG-DTA測定を行ったところ、5%重量減少は400℃であった。その結果を図12に示す。
実施例20で得られたHB-TAM-FA(0.1g)を、シクロヘキサノン0.9gに溶解し、薄黄色透明溶液を得た。得られたポリマーワニスをガラス基板上にスピンコーターを用いて200rpmで5秒間、2000rpmで30秒間スピンコートし、100℃で1分、300℃で5分間加熱して溶媒を除去し、被膜を得た。得られた被膜の屈折率を測定したところ、550nmにおける屈折率は、1.818であった。
TAmD32の1H-NMRスペクトルの測定結果を図13に示す。得られたTAmD32は式(1)で表される構造単位を有する化合物である。TAmD32のGPC(NMP系)によるポリスチレン換算で測定される重量平均分子量Mwは32,100、多分散度Mw/Mnは4.9であった。
実施例2と同様にして、実施例23で得られたTAmD32のTG-DTA測定を行ったところ、5%重量減少は427℃であった。その結果を図14に示す。
実施例23で得られたTAmD32(0.1g)を、シクロヘキサノン0.9gに溶解し、薄黄色透明溶液を得た。得られたポリマーワニスをガラス基板上にスピンコーターを用いて200rpmで5秒間、2000rpmで30秒間スピンコートし、100℃で1分、250℃で5分間加熱して溶媒を除去し、被膜を得た。得られた被膜の屈折率を測定したところ、550nmにおける屈折率は、1.824であった。
Claims (17)
- 下記式(1)で表される繰り返し単位構造を含むことを特徴とするトリアジン環含有重合体。
で示される基を表す。〕} - 前記Ar1およびAr2の組み合わせが、前記式(5)~(12)および(14)~(18)で示される群から選ばれる2種である請求項1記載のトリアジン環含有重合体。
- 前記Ar1およびAr2の組み合わせが、前記式(7)、(11)、(12)、(14)および(15)で示される群から選ばれる2種である請求項1記載のトリアジン環含有重合体。
- 少なくとも1つの末端が、アルキル基、アラルキル基、アリール基、アルキルアミノ基、アルコキシシリル基含有アルキルアミノ基、アラルキルアミノ基、アリールアミノ基、アルコキシ基、アラルキルオキシ基、アリールオキシ基、またはエステル基でキャップされている請求項1~7のいずれか1項記載のトリアジン環含有重合体。
- 少なくとも1つのトリアジン環末端を有し、このトリアジン環末端が、アルキル基、アラルキル基、アリール基、アルキルアミノ基、アルコキシシリル基含有アルキルアミノ基、アラルキルアミノ基、アリールアミノ基、アルコキシ基、アラルキルオキシ基、アリールオキシ基、またはエステル基でキャップされている請求項8記載のトリアジン環含有重合体。
- 請求項1~9のいずれか1項記載のトリアジン環含有重合体を含む膜形成用組成物。
- 請求項10記載の膜形成用組成物から得られる膜。
- 請求項1~9のいずれか1項記載のトリアジン環含有重合体を含む膜。
- 基材と、この基材上に形成された請求項11または12記載の膜とを備える電子デバイス。
- 基材と、この基材上に形成された請求項11または12記載の膜とを備える光学部材。
- 請求項11または12記載の膜を少なくとも1層備える、電荷結合素子または相補性金属酸化膜半導体からなる固体撮像素子。
- 請求項11または12記載の膜をカラーフィルター上の平坦化層として備える固体撮像素子。
- 請求項10記載の膜形成用組成物からなる、固体撮像素子用レンズ材料、平坦化材料または埋め込み材料。
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2012541819A JP5742852B2 (ja) | 2010-11-01 | 2011-10-27 | トリアジン環含有重合体およびそれを含む膜形成用組成物 |
CN201180060900.XA CN103261273B (zh) | 2010-11-01 | 2011-10-27 | 含三嗪环的聚合物和含有该聚合物的成膜用组合物 |
EP11837918.9A EP2636697B1 (en) | 2010-11-01 | 2011-10-27 | Triazine ring-containing polymer and film-forming composition containing same |
KR1020187009508A KR101922506B1 (ko) | 2010-11-01 | 2011-10-27 | 트리아진환 함유 중합체 및 그것을 함유하는 막 형성용 조성물 |
US13/882,679 US9243110B2 (en) | 2010-11-01 | 2011-10-27 | Triazine ring-containing polymer and film-forming composition containing same |
KR1020137013874A KR101873006B1 (ko) | 2010-11-01 | 2011-10-27 | 트리아진환 함유 중합체 및 그것을 함유하는 막 형성용 조성물 |
US14/678,426 US9469729B2 (en) | 2010-11-01 | 2015-04-03 | Triazine ring-containing polymer and film-forming composition containing same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010-245380 | 2010-11-01 | ||
JP2010245380 | 2010-11-01 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US13/882,679 A-371-Of-International US9243110B2 (en) | 2010-11-01 | 2011-10-27 | Triazine ring-containing polymer and film-forming composition containing same |
US14/678,426 Division US9469729B2 (en) | 2010-11-01 | 2015-04-03 | Triazine ring-containing polymer and film-forming composition containing same |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2012060268A1 true WO2012060268A1 (ja) | 2012-05-10 |
Family
ID=46024383
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2011/074749 WO2012060268A1 (ja) | 2010-11-01 | 2011-10-27 | トリアジン環含有重合体およびそれを含む膜形成用組成物 |
Country Status (7)
Country | Link |
---|---|
US (2) | US9243110B2 (ja) |
EP (1) | EP2636697B1 (ja) |
JP (1) | JP5742852B2 (ja) |
KR (2) | KR101873006B1 (ja) |
CN (1) | CN103261273B (ja) |
TW (1) | TWI532763B (ja) |
WO (1) | WO2012060268A1 (ja) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013097917A (ja) * | 2011-10-28 | 2013-05-20 | Denso Corp | 有機el装置およびその製造方法 |
JP2014141597A (ja) * | 2013-01-24 | 2014-08-07 | Nissan Chem Ind Ltd | トリアジン環含有重合体およびそれを含む膜形成用組成物 |
JP2014162829A (ja) * | 2013-02-22 | 2014-09-08 | Idemitsu Kosan Co Ltd | トリアジン環含有線状ポリマーからなる高屈折率材料 |
WO2014208745A1 (ja) * | 2013-06-28 | 2014-12-31 | 住友理工株式会社 | 光透過性積層体 |
WO2015072474A1 (ja) * | 2013-11-13 | 2015-05-21 | 日産化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
JP2016050293A (ja) * | 2014-09-02 | 2016-04-11 | 国立大学法人岩手大学 | ハイパーブランチポリアミド及びこれを含む膜形成用組成物 |
WO2017002797A1 (ja) * | 2015-06-30 | 2017-01-05 | 住友理工株式会社 | 光透過性積層体 |
JP2017047552A (ja) * | 2015-08-31 | 2017-03-09 | 住友理工株式会社 | 光透過性積層体 |
JP2017065243A (ja) * | 2015-09-30 | 2017-04-06 | 住友理工株式会社 | 光透過性積層体 |
JP2018044135A (ja) * | 2016-09-16 | 2018-03-22 | 出光興産株式会社 | 自立フィルム、電子デバイス、発光デバイス及び光学デバイス |
WO2018097000A1 (ja) * | 2016-11-22 | 2018-05-31 | 出光興産株式会社 | トリアジン環含有重合体及びそれを用いた組成物 |
Families Citing this family (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103429664B (zh) * | 2011-02-15 | 2016-05-11 | 日产化学工业株式会社 | 光固化型膜形成用组合物及固化膜的制造方法 |
WO2015125721A1 (ja) * | 2014-02-18 | 2015-08-27 | 日産化学工業株式会社 | 電荷輸送性ワニス |
US9592470B2 (en) | 2014-05-27 | 2017-03-14 | International Business Machines Corporation | Sulfur scavenging materials for filters and coatings |
US9120897B1 (en) | 2014-05-27 | 2015-09-01 | International Business Machines Corporation | Preparation of thioether polymers |
US9120899B1 (en) | 2014-06-02 | 2015-09-01 | International Business Machines Corporation | Preparation of functional polysulfones |
US9469660B2 (en) | 2014-06-03 | 2016-10-18 | International Business Machines Corporation | Sulfur scavenging materials comprising hexahydrotriazine-modified particle |
US9389181B2 (en) | 2014-06-06 | 2016-07-12 | International Business Machines Corporation | Methods and apparatus for detecting metals in liquids |
US9656239B2 (en) | 2014-06-16 | 2017-05-23 | International Business Machines Corporation | Apparatus for controlling metals in liquids |
US9296863B2 (en) | 2014-06-16 | 2016-03-29 | International Business Machines Corporation | Preparation of poly(octatriazacane) |
US9271498B2 (en) | 2014-06-19 | 2016-03-01 | International Business Machines Corporation | Antimicrobial PHT coatings |
US9352045B2 (en) | 2014-06-20 | 2016-05-31 | International Business Machines Corporation | Methods and materials for therapeutic delivery |
US9512332B2 (en) | 2014-06-27 | 2016-12-06 | International Busuiness Machines Corporation | Soluble, processable polyhemiaminals and polyhexahydrotriazines |
US9587073B2 (en) | 2014-07-24 | 2017-03-07 | International Business Machines Corporation | Thermoplastic toughening of PHT's |
US9255172B1 (en) | 2014-08-05 | 2016-02-09 | International Business Machines Corporation | High-performance, filler-reinforced, recyclable composite materials |
CN106715532B (zh) * | 2014-08-13 | 2019-10-11 | 日产化学工业株式会社 | 含有三嗪环的聚合物和包含其的组合物 |
US10023735B2 (en) | 2014-08-18 | 2018-07-17 | International Business Machines Corporation | 3D printing with PHT/PHA based materials and polymerizable monomers |
US9957345B2 (en) | 2014-08-18 | 2018-05-01 | International Business Machines Corporation | 3D printing with PHT based materials |
US9453108B2 (en) | 2014-08-22 | 2016-09-27 | International Business Machines Corporation | Flame retardant PHT compositions |
US9676891B2 (en) | 2014-08-22 | 2017-06-13 | International Business Machines Corporation | Synthesis of dynamic covalent 3D constructs |
US9422378B2 (en) | 2014-10-09 | 2016-08-23 | International Business Machines Corporation | Hexahydrotriazine, dithiazine, and thioether functionalized materials |
US9303186B1 (en) | 2014-10-16 | 2016-04-05 | International Business Machines Corporation | PHT powder coating materials |
US9777116B2 (en) | 2014-10-16 | 2017-10-03 | International Business Machines Corporation | Porous/nanoporous PHT |
JP2016148777A (ja) * | 2015-02-12 | 2016-08-18 | アーゼッド・エレクトロニック・マテリアルズ(ルクセンブルグ)ソシエテ・ア・レスポンサビリテ・リミテ | 下層膜形成用組成物、およびそれを用いた下層膜の形成方法 |
CN107922614B (zh) * | 2015-06-03 | 2021-02-02 | 日产化学工业株式会社 | 含有三嗪环的聚合物和包含其的膜形成用组合物 |
US10080806B2 (en) | 2015-08-19 | 2018-09-25 | International Business Machines Corporation | Sulfur-containing polymers from hexahydrotriazine and dithiol precursors as a carrier for active agents |
US9758620B2 (en) | 2015-09-03 | 2017-09-12 | International Business Machines Corporation | Tailorable viscoelastic properties of PEG-hemiaminal organogel networks |
US9550863B1 (en) | 2015-10-05 | 2017-01-24 | International Business Machines Corporation | Polymers from stabilized imines |
US9534084B1 (en) | 2015-11-02 | 2017-01-03 | International Business Machines Corporation | High molecular weight polythioaminals from a single monomer |
US9873766B2 (en) | 2015-11-24 | 2018-01-23 | International Business Machines Corporation | Systems chemistry approach to polyhexahydrotriazine polymeric structures |
US9862802B2 (en) | 2015-11-30 | 2018-01-09 | International Business Machines Corporation | Poly(thioaminal) probe based lithography |
US9828467B2 (en) | 2016-02-05 | 2017-11-28 | International Business Machines Corporation | Photoresponsive hexahydrotriazine polymers |
CN109071807B (zh) * | 2016-02-09 | 2021-07-06 | 日产化学株式会社 | 含有三嗪环的聚合物和包含该聚合物的组合物 |
JP6574731B2 (ja) * | 2016-03-25 | 2019-09-11 | 富士フイルム株式会社 | 光学フィルム、偏光板、及び画像表示装置 |
WO2019093203A1 (ja) * | 2017-11-08 | 2019-05-16 | 日産化学株式会社 | トリアジン環含有重合体およびそれを含む組成物 |
US11180612B2 (en) | 2018-08-24 | 2021-11-23 | Samsung Electronics Co., Ltd. | Triazine ring-containing polymer, and thermoplastic article and optical component including the same |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS323145B1 (ja) * | 1954-10-12 | 1957-05-27 | ||
JPS57187321A (en) * | 1981-05-07 | 1982-11-18 | Hoechst Ag | Poly-bis-triazinylaminotriazinyl amine, manufacture and use |
JPH07113009A (ja) * | 1993-10-18 | 1995-05-02 | Alps Electric Co Ltd | 溶媒可溶性芳香族ポリアミンおよびその製造方法 |
US5886130A (en) | 1995-11-02 | 1999-03-23 | Maxdem Incorporated | Polyphenylene co-polymers |
JP2000053659A (ja) | 1998-08-10 | 2000-02-22 | Asahi Chem Ind Co Ltd | トリアジン系重合物質 |
JP2001503077A (ja) * | 1996-09-16 | 2001-03-06 | バイエル・アクチエンゲゼルシヤフト | トリアジン重合体そして電界発光装置におけるそれの使用 |
JP2007246877A (ja) | 2005-10-03 | 2007-09-27 | Toray Ind Inc | シロキサン系樹脂組成物、光学物品およびシロキサン系樹脂組成物の製造方法 |
JP2008024832A (ja) | 2006-07-21 | 2008-02-07 | Tokyo Ohka Kogyo Co Ltd | 高屈折率材料 |
WO2010128661A1 (ja) * | 2009-05-07 | 2010-11-11 | 日産化学工業株式会社 | トリアジン環含有重合体およびそれを含む膜形成用組成物 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6323310B1 (en) * | 2000-04-19 | 2001-11-27 | Brewer Science, Inc. | Anti-reflective coating compositions comprising polymerized aminoplasts |
JP2004315716A (ja) * | 2003-04-18 | 2004-11-11 | Toyo Ink Mfg Co Ltd | 顔料分散剤、それを用いた顔料組成物および顔料分散体 |
JP2006070248A (ja) | 2004-08-02 | 2006-03-16 | Showa Denko Kk | 電子部品用硬化性トリアジン組成物、その製造方法及び硬化物 |
WO2010128660A1 (ja) * | 2009-05-07 | 2010-11-11 | 日産化学工業株式会社 | カーボンナノチューブ分散・可溶化剤 |
CN101717396A (zh) * | 2009-11-27 | 2010-06-02 | 南京邮电大学 | 三嗪类光电功能材料及制备和应用方法 |
-
2011
- 2011-10-27 WO PCT/JP2011/074749 patent/WO2012060268A1/ja active Application Filing
- 2011-10-27 JP JP2012541819A patent/JP5742852B2/ja active Active
- 2011-10-27 US US13/882,679 patent/US9243110B2/en active Active
- 2011-10-27 CN CN201180060900.XA patent/CN103261273B/zh active Active
- 2011-10-27 EP EP11837918.9A patent/EP2636697B1/en active Active
- 2011-10-27 KR KR1020137013874A patent/KR101873006B1/ko active IP Right Grant
- 2011-10-27 KR KR1020187009508A patent/KR101922506B1/ko active IP Right Grant
- 2011-10-31 TW TW100139582A patent/TWI532763B/zh active
-
2015
- 2015-04-03 US US14/678,426 patent/US9469729B2/en active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS323145B1 (ja) * | 1954-10-12 | 1957-05-27 | ||
JPS57187321A (en) * | 1981-05-07 | 1982-11-18 | Hoechst Ag | Poly-bis-triazinylaminotriazinyl amine, manufacture and use |
JPH07113009A (ja) * | 1993-10-18 | 1995-05-02 | Alps Electric Co Ltd | 溶媒可溶性芳香族ポリアミンおよびその製造方法 |
US5886130A (en) | 1995-11-02 | 1999-03-23 | Maxdem Incorporated | Polyphenylene co-polymers |
JP2001503077A (ja) * | 1996-09-16 | 2001-03-06 | バイエル・アクチエンゲゼルシヤフト | トリアジン重合体そして電界発光装置におけるそれの使用 |
JP2000053659A (ja) | 1998-08-10 | 2000-02-22 | Asahi Chem Ind Co Ltd | トリアジン系重合物質 |
JP2007246877A (ja) | 2005-10-03 | 2007-09-27 | Toray Ind Inc | シロキサン系樹脂組成物、光学物品およびシロキサン系樹脂組成物の製造方法 |
JP2008024832A (ja) | 2006-07-21 | 2008-02-07 | Tokyo Ohka Kogyo Co Ltd | 高屈折率材料 |
WO2010128661A1 (ja) * | 2009-05-07 | 2010-11-11 | 日産化学工業株式会社 | トリアジン環含有重合体およびそれを含む膜形成用組成物 |
Non-Patent Citations (5)
Title |
---|
"Saishin UV Koka Gijutsu", 1991, GIJUTSU JOHO KYOKAI KK, pages: 159 |
JOURNAL OF APPLIED POLYMER SCIENCE, vol. 106, 2007, pages 95 - 102 |
MAHAPATRA S.S. ET AL.: "Effect of structure and concentration of polymer, metal ion and pH of the medium on the fluorescence characteristics of hyperbranched polyamines", JOURNAL OF LUMINESCENCE, vol. 128, no. 12, 2008, pages 1917 - 1921, XP025409876 * |
See also references of EP2636697A4 |
ZHANG W. ET AL.: "Structure-Activity Relationships in Dendrimers Based on Triazines: Gelation Depends on Choice of Linking and Surface Groups", MACROMOLECULES, vol. 35, no. 24, 2002, pages 9015 - 9021, XP055085420 * |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2013097917A (ja) * | 2011-10-28 | 2013-05-20 | Denso Corp | 有機el装置およびその製造方法 |
JP2014141597A (ja) * | 2013-01-24 | 2014-08-07 | Nissan Chem Ind Ltd | トリアジン環含有重合体およびそれを含む膜形成用組成物 |
JP2014162829A (ja) * | 2013-02-22 | 2014-09-08 | Idemitsu Kosan Co Ltd | トリアジン環含有線状ポリマーからなる高屈折率材料 |
WO2014208745A1 (ja) * | 2013-06-28 | 2014-12-31 | 住友理工株式会社 | 光透過性積層体 |
JP5959746B2 (ja) * | 2013-06-28 | 2016-08-02 | 住友理工株式会社 | 光透過性積層体 |
JPWO2015072474A1 (ja) * | 2013-11-13 | 2017-03-16 | 日産化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
WO2015072474A1 (ja) * | 2013-11-13 | 2015-05-21 | 日産化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
CN105874879A (zh) * | 2013-11-13 | 2016-08-17 | 日产化学工业株式会社 | 有机电致发光元件 |
CN105874879B (zh) * | 2013-11-13 | 2018-11-13 | 日产化学工业株式会社 | 有机电致发光元件 |
JP2016050293A (ja) * | 2014-09-02 | 2016-04-11 | 国立大学法人岩手大学 | ハイパーブランチポリアミド及びこれを含む膜形成用組成物 |
WO2017002797A1 (ja) * | 2015-06-30 | 2017-01-05 | 住友理工株式会社 | 光透過性積層体 |
JP2017047552A (ja) * | 2015-08-31 | 2017-03-09 | 住友理工株式会社 | 光透過性積層体 |
JP2017065243A (ja) * | 2015-09-30 | 2017-04-06 | 住友理工株式会社 | 光透過性積層体 |
JP2018044135A (ja) * | 2016-09-16 | 2018-03-22 | 出光興産株式会社 | 自立フィルム、電子デバイス、発光デバイス及び光学デバイス |
WO2018097000A1 (ja) * | 2016-11-22 | 2018-05-31 | 出光興産株式会社 | トリアジン環含有重合体及びそれを用いた組成物 |
CN109937227A (zh) * | 2016-11-22 | 2019-06-25 | 出光兴产株式会社 | 含三嗪环的聚合物和使用其的组合物 |
JPWO2018097000A1 (ja) * | 2016-11-22 | 2019-10-17 | 出光興産株式会社 | トリアジン環含有重合体及びそれを用いた組成物 |
CN109937227B (zh) * | 2016-11-22 | 2021-12-21 | 出光兴产株式会社 | 含三嗪环的聚合物和使用其的组合物 |
US11673998B2 (en) | 2016-11-22 | 2023-06-13 | Idemitsu Kosan Co., Ltd. | Triazine-ring-containing polymer and composition in which same is used |
Also Published As
Publication number | Publication date |
---|---|
JPWO2012060268A1 (ja) | 2014-05-12 |
US20150210808A1 (en) | 2015-07-30 |
US9469729B2 (en) | 2016-10-18 |
TWI532763B (zh) | 2016-05-11 |
KR101873006B1 (ko) | 2018-07-02 |
EP2636697A4 (en) | 2014-05-07 |
US20130289203A1 (en) | 2013-10-31 |
EP2636697B1 (en) | 2018-08-15 |
JP5742852B2 (ja) | 2015-07-01 |
EP2636697A1 (en) | 2013-09-11 |
KR20180037327A (ko) | 2018-04-11 |
TW201233712A (en) | 2012-08-16 |
US9243110B2 (en) | 2016-01-26 |
CN103261273B (zh) | 2015-09-16 |
KR101922506B1 (ko) | 2018-11-27 |
KR20130100180A (ko) | 2013-09-09 |
CN103261273A (zh) | 2013-08-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5742852B2 (ja) | トリアジン環含有重合体およびそれを含む膜形成用組成物 | |
JP6003952B2 (ja) | トリアジン環含有重合体およびそれを含む膜形成用組成物 | |
JP5598258B2 (ja) | トリアジン環含有重合体含有高屈折率膜を備える電子デバイス | |
JP5857963B2 (ja) | トリアジン環含有重合体およびそれを含む膜形成用組成物 | |
JP5842822B2 (ja) | 膜形成用組成物 | |
WO2012026451A1 (ja) | 膜形成用組成物 | |
JP5691408B2 (ja) | トリアジン環含有重合体およびそれを含む膜形成用組成物 | |
JP6085975B2 (ja) | トリアジン環含有重合体およびそれを含む膜形成用組成物 | |
JP6061015B2 (ja) | トリアジン環含有重合体からなる高屈折率材料を含む高屈折率膜 | |
JP5794235B2 (ja) | トリアジン環含有重合体およびそれを含む膜形成用組成物 | |
JP6020469B2 (ja) | トリアジン環含有重合体およびそれを含む膜形成用組成物 | |
JP5842959B2 (ja) | トリアジン環含有重合体からなる高屈折率材料およびそれを含む高屈折率膜形成用組成物 | |
JP2015227462A (ja) | トリアジン環含有重合体 | |
JP6052378B2 (ja) | トリアジン環含有重合体を含む膜形成用組成物 | |
JP2014169452A (ja) | トリアジン環含有重合体およびそれを含む膜形成用組成物 | |
JP5880630B2 (ja) | トリアジン環含有重合体 | |
JP5573603B2 (ja) | トリアジン環含有重合体およびそれを含む膜形成用組成物 | |
JP6669206B2 (ja) | トリアジン環含有重合体を含む高屈折率膜形成用組成物 | |
JP6112296B2 (ja) | トリアジン環含有重合体およびそれを含む膜形成用組成物 | |
JP2019214733A (ja) | トリアジン環含有重合体 | |
JP2017133035A (ja) | トリアジン環含有重合体 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 11837918 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2012541819 Country of ref document: JP Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2011837918 Country of ref document: EP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
ENP | Entry into the national phase |
Ref document number: 20137013874 Country of ref document: KR Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 13882679 Country of ref document: US |