CN109715698A - Alkali soluble resins and alkali soluble type radiation sensitive resin composition containing unsaturated group - Google Patents
Alkali soluble resins and alkali soluble type radiation sensitive resin composition containing unsaturated group Download PDFInfo
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- CN109715698A CN109715698A CN201780056482.4A CN201780056482A CN109715698A CN 109715698 A CN109715698 A CN 109715698A CN 201780056482 A CN201780056482 A CN 201780056482A CN 109715698 A CN109715698 A CN 109715698A
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- CN
- China
- Prior art keywords
- methyl
- general formula
- alkali soluble
- acrylate
- soluble resins
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000003513 alkali Substances 0.000 title claims abstract description 101
- 229920005989 resin Polymers 0.000 title claims abstract description 76
- 239000011347 resin Substances 0.000 title claims abstract description 76
- 230000005855 radiation Effects 0.000 title claims description 21
- 239000011342 resin composition Substances 0.000 title claims description 19
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims abstract description 62
- 239000004593 Epoxy Substances 0.000 claims abstract description 50
- 239000002253 acid Substances 0.000 claims abstract description 50
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 34
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 19
- 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 claims abstract description 12
- 239000000376 reactant Substances 0.000 claims abstract description 9
- 239000004615 ingredient Substances 0.000 claims description 68
- 239000010408 film Substances 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 150000008065 acid anhydrides Chemical class 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 8
- 150000003628 tricarboxylic acids Chemical class 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 7
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 230000008023 solidification Effects 0.000 claims 1
- 238000007711 solidification Methods 0.000 claims 1
- 238000011161 development Methods 0.000 abstract description 15
- 230000006978 adaptation Effects 0.000 abstract description 13
- 239000007787 solid Substances 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 38
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 31
- -1 halogen radical Chemical class 0.000 description 25
- 239000000243 solution Substances 0.000 description 22
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 21
- WUZBGMQIKXKYMX-UHFFFAOYSA-N 6-methoxyhexanoic acid Chemical class COCCCCCC(O)=O WUZBGMQIKXKYMX-UHFFFAOYSA-N 0.000 description 20
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 20
- 238000002156 mixing Methods 0.000 description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 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 11
- 150000008064 anhydrides Chemical class 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 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 8
- NUDSREQIJYWLRA-UHFFFAOYSA-N 4-[9-(4-hydroxy-3-methylphenyl)fluoren-9-yl]-2-methylphenol Chemical class C1=C(O)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(O)=CC=2)=C1 NUDSREQIJYWLRA-UHFFFAOYSA-N 0.000 description 7
- 229930185605 Bisphenol Natural products 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 229940106691 bisphenol a Drugs 0.000 description 6
- 150000002148 esters Chemical group 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- UTLJATUUOXBWPZ-UHFFFAOYSA-N C(C=C)(=O)OC.[O] Chemical compound C(C=C)(=O)OC.[O] UTLJATUUOXBWPZ-UHFFFAOYSA-N 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IPTNXMGXEGQYSY-UHFFFAOYSA-N acetic acid;1-methoxybutan-1-ol Chemical compound CC(O)=O.CCCC(O)OC IPTNXMGXEGQYSY-UHFFFAOYSA-N 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical class CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 235000003642 hunger Nutrition 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 2
- DJKGDNKYTKCJKD-BPOCMEKLSA-N (1s,4r,5s,6r)-1,2,3,4,7,7-hexachlorobicyclo[2.2.1]hept-2-ene-5,6-dicarboxylic acid Chemical compound ClC1=C(Cl)[C@]2(Cl)[C@H](C(=O)O)[C@H](C(O)=O)[C@@]1(Cl)C2(Cl)Cl DJKGDNKYTKCJKD-BPOCMEKLSA-N 0.000 description 1
- VMHYWKBKHMYRNF-UHFFFAOYSA-N (2-chlorophenyl)-phenylmethanone Chemical compound ClC1=CC=CC=C1C(=O)C1=CC=CC=C1 VMHYWKBKHMYRNF-UHFFFAOYSA-N 0.000 description 1
- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-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
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- LZWVPGJPVCYAOC-UHFFFAOYSA-N 2,3-diphenylanthracene-9,10-dione Chemical compound C=1C=CC=CC=1C=1C=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=1C1=CC=CC=C1 LZWVPGJPVCYAOC-UHFFFAOYSA-N 0.000 description 1
- MFUCEQWAFQMGOR-UHFFFAOYSA-N 2,4-diethyl-9h-thioxanthene Chemical compound C1=CC=C2CC3=CC(CC)=CC(CC)=C3SC2=C1 MFUCEQWAFQMGOR-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 1
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- BSMGLVDZZMBWQB-UHFFFAOYSA-N 2-methyl-1-phenylpropan-1-one Chemical compound CC(C)C(=O)C1=CC=CC=C1 BSMGLVDZZMBWQB-UHFFFAOYSA-N 0.000 description 1
- ATTLFLQPHSUNBK-UHFFFAOYSA-N 2-methyl-9h-thioxanthene Chemical compound C1=CC=C2CC3=CC(C)=CC=C3SC2=C1 ATTLFLQPHSUNBK-UHFFFAOYSA-N 0.000 description 1
- ODGCZQFTJDEYNI-UHFFFAOYSA-N 2-methylcyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1(C)C=CCCC1C(O)=O ODGCZQFTJDEYNI-UHFFFAOYSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- JRXXEXVXTFEBIY-UHFFFAOYSA-N 3-ethoxypropanoic acid Chemical compound CCOCCC(O)=O JRXXEXVXTFEBIY-UHFFFAOYSA-N 0.000 description 1
- PFCHFHIRKBAQGU-UHFFFAOYSA-N 3-hexanone Chemical compound CCCC(=O)CC PFCHFHIRKBAQGU-UHFFFAOYSA-N 0.000 description 1
- VUZHZDBMVSHDRE-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.OCCCOC(=O)C=C VUZHZDBMVSHDRE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- FFXHMHZWNBZCBI-UHFFFAOYSA-N 9H-fluorene 2-phenylphenol Chemical class C1=CC=CC=2C3=CC=CC=C3CC12.C1(=CC=CC=C1)C1=C(C=CC=C1)O FFXHMHZWNBZCBI-UHFFFAOYSA-N 0.000 description 1
- ISKXXTBQZYPQBO-UHFFFAOYSA-N 9H-fluorene naphthalen-1-ol Chemical class C1=CC=C2C(O)=CC=CC2=C1.C1=CC=C2C(O)=CC=CC2=C1.C1=CC=C2CC3=CC=CC=C3C2=C1 ISKXXTBQZYPQBO-UHFFFAOYSA-N 0.000 description 1
- PQJUJGAVDBINPI-UHFFFAOYSA-N 9H-thioxanthene Chemical compound C1=CC=C2CC3=CC=CC=C3SC2=C1 PQJUJGAVDBINPI-UHFFFAOYSA-N 0.000 description 1
- IXCOKTMGCRJMDR-UHFFFAOYSA-N 9h-fluorene;phenol Chemical group OC1=CC=CC=C1.OC1=CC=CC=C1.C1=CC=C2CC3=CC=CC=C3C2=C1 IXCOKTMGCRJMDR-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 1
- XCBBNTFYSLADTO-UHFFFAOYSA-N Methyl-pentyl-glyoxal Natural products CCCCCC(=O)C(C)=O XCBBNTFYSLADTO-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- SEEVRZDUPHZSOX-WPWMEQJKSA-N [(e)-1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(\C)=N\OC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-WPWMEQJKSA-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
- SWHLOXLFJPTYTL-UHFFFAOYSA-N [2-methyl-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(COC(=O)C(C)=C)COC(=O)C(C)=C SWHLOXLFJPTYTL-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- GJSJZQZEDAUFBH-UHFFFAOYSA-N benzene;pentan-3-one Chemical compound CCC(=O)CC.C1=CC=CC=C1 GJSJZQZEDAUFBH-UHFFFAOYSA-N 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 229940074654 diuril Drugs 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- KBHMHROOFHVLBA-UHFFFAOYSA-N metamfepramone Chemical compound CN(C)C(C)C(=O)C1=CC=CC=C1 KBHMHROOFHVLBA-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- RLFXWALMKAWBBF-UHFFFAOYSA-N methyl prop-2-enoate propane-1,2,3-triol Chemical compound C(C=C)(=O)OC.OCC(O)CO RLFXWALMKAWBBF-UHFFFAOYSA-N 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 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
- JMXROTHPANUTOJ-UHFFFAOYSA-H naphthol green b Chemical compound [Na+].[Na+].[Na+].[Fe+3].C1=C(S([O-])(=O)=O)C=CC2=C(N=O)C([O-])=CC=C21.C1=C(S([O-])(=O)=O)C=CC2=C(N=O)C([O-])=CC=C21.C1=C(S([O-])(=O)=O)C=CC2=C(N=O)C([O-])=CC=C21 JMXROTHPANUTOJ-UHFFFAOYSA-H 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0385—Macromolecular compounds which are rendered insoluble or differentially wettable using epoxidised novolak resin
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10D—INORGANIC ELECTRIC SEMICONDUCTOR DEVICES
- H10D30/00—Field-effect transistors [FET]
- H10D30/60—Insulated-gate field-effect transistors [IGFET]
- H10D30/67—Thin-film transistors [TFT]
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
- Polyesters Or Polycarbonates (AREA)
- Optical Filters (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Abstract
The present invention provides a kind of low acid value, alkali solubility, development adaptation, resolution ratio and the excellent alkali soluble resins containing unsaturated group of electrology characteristic.A kind of alkali soluble resins containing unsaturated group is provided, it is characterized in that, its epoxy (methyl) acrylate and (c) reactant of tetrabasic carboxylic acid or its acid dianhydride for for (a) there is epoxy (methyl) acrylate of fluorene skeleton, (b) not to have fluorene skeleton.
Description
Technical field
The present invention relates to alkali soluble resins and alkali soluble type radiation sensitive resin composition containing unsaturated group.
Background technique
In the past, the alkali soluble resins with fluorene skeleton was due to the dispersibility of pigment, chemical resistance, electrology characteristic, resistance to
It is hot, sensitivity is excellent, suitable for black matrix formation photoresist used in the manufacture in the colour filter of LCD, half
The photoresist of conductor manufacture.As the alkali soluble resins with fluorene skeleton, for example, being proposed in patent document 1 following
Photopolymerizable unsaturated compound, be using making to have the epoxy acrylate of bis-phenol fluorene skeleton to react with tetracarboxylic dianhydride and
It is formed after oligomer and what the two-stage as envelope chain reacted is carried out to terminal hydroxyl using dicarboxylic anhydride.
But for the photopolymerizable unsaturated compound of patent document 1, generally to ensure that developability and it is necessary
High acid value is designed to, as a result, the height requirement in recent years such as development adaptation, resolution ratio, electrology characteristic can not be coped with.Example
Such as, if reducing acid value in order to improve electrology characteristic, there are alkali solubilities to significantly reduce, can not obtain and the balance of developability
Problem.Although its reason not yet determines, however, it is thought that the resin with fluorene skeleton is easy to take packed structures, crystallinity high, because
This alkali solubility in the case where reducing acid value can significantly reduce.
Existing technical literature
Patent document
Patent document 1: Japanese Unexamined Patent Publication 2001-354735 bulletin
Summary of the invention
Problems to be solved by the invention
A kind of the purpose of the present invention is to provide acid values low, alkali solubility, development adaptation, resolution ratio and electrology characteristic are excellent
The alkali soluble resins containing unsaturated group.
Means for solving the problems
Present inventor has performed further investigations, as a result, it has been found that, by the way that a part of fluorene skeleton is replaced as non-fluorene skeleton, energy
Enough destroy the packed structures of fluorene skeleton.And it was found that by the structure from epoxy (methyl) acrylate with fluorene skeleton
A part is replaced as the alkali solubility containing unsaturated group of the structure from epoxy (methyl) acrylate for not having fluorene skeleton
Even if resin, in the case where acid value is low, alkali solubility, development adaptation, resolution ratio and electrology characteristic are also excellent, this completes
The present invention.
That is, the first alkali soluble resins of the invention containing unsaturated group is characterized in that, it is
(a) with fluorene skeleton epoxy (methyl) acrylate,
(b) without fluorene skeleton epoxy (methyl) acrylate and
(c) tetrabasic carboxylic acid or its acid dianhydride
Reactant.
First alkali soluble resins of the invention containing unsaturated group may be
(a) with fluorene skeleton epoxy (methyl) acrylate,
(b) without fluorene skeleton epoxy (methyl) acrylate,
(c) tetrabasic carboxylic acid or its acid dianhydride and
(d) dicarboxylic acids or tricarboxylic acids or its acid anhydrides
Reactant.
First alkali soluble resins of the invention containing unsaturated group is preferred: (b) ingredient has cyclic structure.
Second alkali soluble resins of the invention containing unsaturated group is characterized in that, is indicated by the following general formula (1).
[changing 1]
(in general formula (1), A indicates structure shown in the following general formula (2) or (3) independently of each other, ties shown in general formula (2)
The molar ratio of structure shown in structure and general formula (3) is general formula (2): general formula (3)=90:10~20:80, B are indicated independently of each other
Structure shown in the following general formula (4), C indicate structure shown in hydrogen atom or the following general formula (5) independently of each other, and l is repeat number
Average value and independently of each other indicate 0~20, m be repeat number average value and indicate 1~20, n indicate 0 independently of each other
~20 integer.)
[changing 2]
(in general formula (2), D indicates to remove epoxy (methyl) acrylic acid from epoxy (methyl) acrylate with fluorene skeleton
Bivalent group after esteratic site, R1Hydrogen atom or methyl are indicated independently of each other.)
[changing 3]
(in general formula (3), E indicates to remove epoxy (methyl) propylene from epoxy (methyl) acrylate for not having fluorene skeleton
Multivalence group behind acid esters position, R1Indicate that hydrogen atom or methyl, n indicate 0~20 integer independently of each other.)
-CO-X(COOH)2-CO-(4)
(in general formula (4), X indicates tetrabasic carboxylic acid residue.)
-CO-Y-(COOH)y(5)
(in general formula (5), Y indicates that 2~4 yuan of polycarboxylic acid residues, y indicate 1~3 integer.)
Second alkali soluble resins of the invention containing unsaturated group is preferred: in general formula (2), D indicates the following general formula (6)
Shown in structure.
[changing 4]
(in general formula (6), R2Hydrogen atom is indicated independently of each other, alkyl, phenyl or the halogen radical that carbon atom number is 1~5
Group, k indicate 0~10 integer.)
Second alkali soluble resins of the invention containing unsaturated group may is that in general formula (1), C indicates general formula (5) institute
The structure shown, and in general formula (5), Y indicates that 2 yuan or 3 yuan of polycarboxylic acid residues, y indicate an integer of 1 or 2.
The first or second alkali soluble resins preferred acid number of the invention containing unsaturated group is 100 or less.
Alkali soluble type radiation sensitive resin composition of the invention is characterized in that, it includes:
(A) first or second alkali soluble resins of the invention containing unsaturated group,
(B) photopolymerization monomer and/or oligomer,
(C) Photoepolymerizationinitiater initiater and
(D) solvent.
Cured film of the invention is characterized in that, is to keep alkali soluble type radiation sensitive resin composition of the invention solid
Made of change.
Colour filter of the invention is characterized in that it includes cured films of the invention.
Thin film transistor (TFT) of the invention is characterized in that it includes cured films of the invention.
The effect of invention
First and second alkali soluble resins of the invention containing unsaturated group are will be from the epoxy (first with fluorene skeleton
Base) acrylate structure a part be replaced as from do not have fluorene skeleton epoxy (methyl) acrylate structure after
Substance, therefore acid value is low, alkali solubility, develop adaptation, resolution ratio and excellent electrical characteristic.
Specific embodiment
<<the first alkali soluble resins of the invention containing unsaturated group>>
First alkali soluble resins of the invention containing unsaturated group is characterized in that, is
(a) with fluorene skeleton epoxy (methyl) acrylate,
(b) without fluorene skeleton epoxy (methyl) acrylate and
(c) tetrabasic carboxylic acid or its acid dianhydride
Reactant.
<epoxy (methyl) acrylate that (a) has fluorene skeleton>
Have epoxy (methyl) acrylate (being hereinafter also referred to as (a) ingredient) of fluorene skeleton without special as (a)
It limits, it can be cited for example that bisphenol fluorene type ring oxygen (methyl) acrylate, 9,9- bis- (3- methyl -4- hydroxy phenyl) fluorenes type ring oxygen
(methyl) acrylate, double phenylphenol fluorenes type ring oxygen (methyl) acrylate, double phenoxetol fluorenes type ring oxygen (methyl) third
Olefin(e) acid ester, bis-naphthol fluorenes type ring oxygen (methyl) acrylate etc..They can be used alone or in combination with two or more.
It should be noted that epoxy (methyl) acrylate refers to (methyl) acrylic acid and contains epoxy group in this specification
Compound ester.In addition, (methyl) acrylic acid refers to acrylic or methacrylic acid in this specification.
<epoxy (methyl) acrylate that (b) does not have fluorene skeleton>
Do not have epoxy (methyl) acrylate (being hereinafter also referred to as (b) ingredient) of fluorene skeleton without spy as (b)
It does not limit, it can be cited for example that bisphenol type epoxy (methyl) acrylate, hydrogenated bisphenol A type epoxy (methyl) acrylate, double
The epoxies (methyl) third containing bisphenol backbone such as phenol AP type ring oxygen (methyl) acrylate, bisphenol F type epoxy (methyl) acrylate
Olefin(e) acid ester, epoxy (methyl) acrylate containing four phenol skeletons, contains naphthalene skeleton at epoxy (methyl) acrylate of the skeleton containing triphenol
Epoxy (methyl) acrylate, epoxy (methyl) acrylate of the skeleton containing novolaks, the epoxy (first containing adamantane framework
Base) acrylate, epoxy (methyl) acrylate containing isocyanuric acid skeleton, the skeleton containing xenol epoxy (methyl) acrylic acid
Ester etc..They can be used alone or in combination with two or more.
It is good from developability, electrology characteristic, heat resistance in first alkali soluble resins of the invention containing unsaturated group
From the aspect of, preferably (b) ingredient has cyclic structure.It is not particularly limited as cyclic structure, it can be cited for example that aromatic rings,
Alicyclic ring, condensed ring, heterocycle etc..They can be separately existed in (b) ingredient, can also be existed simultaneously two or more.
<(c) tetrabasic carboxylic acid or its acid dianhydride>
It is not particularly limited as (c) tetrabasic carboxylic acid or its acid dianhydride (being hereinafter also referred to as (c) ingredient), example can be enumerated
Such as pyromellitic acid, hydrogenation pyromellitic acid, benzophenone tetrabasic carboxylic acid, biphenyltetracarboxyacid acid, Biphenyl Ether tetrabasic carboxylic acid, diphenyl sulfonic acid tetracarboxylic acid
Acid, 4,4 '-hexafluoro propylidene double phthalic acid, 1,2,4,5- cyclopentanetetracarboxylics etc. and their acid dianhydride etc..They can
To be used alone, can also share two or more.
<(d) dicarboxylic acids or tricarboxylic acids or its acid anhydrides>
First alkali soluble resins of the invention containing unsaturated group may be
(a) with fluorene skeleton epoxy (methyl) acrylate,
(b) without fluorene skeleton epoxy (methyl) acrylate,
(c) tetrabasic carboxylic acid or its acid dianhydride and
(d) dicarboxylic acids or tricarboxylic acids or its acid anhydrides
Reactant.As (d) dicarboxylic acids or tricarboxylic acids or its acid anhydrides (being hereinafter also referred to as (d) ingredient) without spy
It does not limit, it can be cited for example that maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydro neighbour benzene two
Formic acid, methylendomethylenetetrahydrophthalic tetrahydrophthalic acid, chlorendic acid, methyl tetrahydrophthalic acid, succinic acid, glutaric acid, inclined benzene
Three acid etc. and their acid anhydrides etc..They can be used alone or in combination with two or more.
<reaction of (a)~(d) ingredient>
In the reaction of (a)~(d) ingredient, the order of addition of each ingredient is not particularly limited, such as is not being used
(d) in the case where ingredient, the method etc. for making (a)~(c) ingredient simultaneous reactions can be enumerated.In addition, in the feelings of use (d) ingredient
Under condition, can enumerate makes the reaction of (a)~(c) ingredient, the method for then reacting (d) ingredient etc..
(a) ingredient and the molar ratio of (b) ingredient are not particularly limited, preferably 90:10~20:80, more preferably 80:
20~20:80.If (a) for the molar ratio of ingredient less than 20, developability is sometimes insufficient；If (a) molar ratio of ingredient is more than 90,
Developability becomes inadequate sometimes when reducing acid value.
In the case where use (d) ingredient, (c) ingredient and the molar ratio of (d) ingredient are not particularly limited, usually
99:1~10:90, preferably 95:5~20:80.It is obtained containing unsaturated group if (d) molar ratio of ingredient is more than 90
The molecular weight of alkali soluble resins (A) reduces, thus it some times happens that the problem of film after prebake remains adherency.
The reaction temperature of (a)~(d) ingredient is not particularly limited, preferably 80~130 DEG C, more preferably 90~110
℃.If reaction temperature, less than 80 DEG C, reaction carries out in which can not be successfully, it is possible to remaining unreacted reactant, if reaction temperature is more than 130
DEG C, the polymerization of (a) ingredient and (b) ingredient partly occurs, sometimes resulting in molecular weight increased dramatically.To the reaction time without spy
It does not limit, preferably 2~24 hours, more preferably 4~20 hours.If the reaction time less than 2 hours, reaction be unable to fully into
Row, it is possible to if the reaction time is more than 24 hours the polymerization of (a) ingredient and (b) ingredient partly occurs for remaining unreacted reactant,
Sometimes resulting in molecular weight increased dramatically.
(a)~(d) reaction of ingredient can carry out in the presence of solvent, catalyst etc. as needed.In addition, anti-at this
Ying Zhong optionally can also be such that other monomers are reacted other than (a)~(d) ingredient.It is not special as other monomers
It limits, it can be cited for example that polyalcohol, epoxide, isocyanate compound, silane coupling agent etc..They can individually make
With can also share two or more.
<<the second alkali soluble resins of the invention containing unsaturated group>>
Second alkali soluble resins of the invention containing unsaturated group is characterized in that, is indicated by the following general formula (1).
[changing 5]
In general formula (1), A indicates structure shown in the following general formula (2) or (3) independently of each other.
[changing 6]
In general formula (2), D indicates to remove epoxy (methyl) acrylate from epoxy (methyl) acrylate with fluorene skeleton
Bivalent group behind position.As epoxy (methyl) acrylate with fluorene skeleton, can enumerate and as first present invention
The alkali soluble resins containing unsaturated group raw material the same substance of (a) ingredient.They can be used alone, and can also close
With two or more.
In general formula (2), from electrology characteristic, heat resistance it is good from the aspect of, D is preferably indicated shown in the following general formula (6)
Structure.
[changing 7]
In general formula (6), R2Hydrogen atom is indicated independently of each other, alkyl, phenyl or the halogen group that carbon atom number is 1~5.
The alkyl for being 1~5 as carbon atom number is not particularly limited, it can be cited for example that methyl, ethyl, propyl, butyl, amyl etc..
It is not particularly limited as halogen group, it can be cited for example that fluorine-based, chloro, bromo, iodo etc..
In general formula (6), k indicate 0~10 integer, preferably 0~7 integer, more preferably 0~5 integer.If k
More than 10, then developability can significantly reduce sometimes.
In general formula (2), R1Hydrogen atom or methyl are indicated independently of each other.
[changing 8]
In general formula (3), E indicates to remove epoxy (methyl) acrylic acid from epoxy (methyl) acrylate for not having fluorene skeleton
Multivalence group after esteratic site.As epoxy (methyl) acrylate for not having fluorene skeleton, can enumerate and as first
The identical substance of (b) ingredient of the raw material of the alkali soluble resins containing unsaturated group of invention.They can be used alone, can also
It is two or more to share.
In general formula (3), R1Hydrogen atom or methyl are indicated independently of each other.
In general formula (3), n indicate 0~20 integer, preferably 0~10 integer, more preferably 0~4 integer.If n is super
20 are crossed, not only resin viscosity increases, workability is deteriorated, but also molecular weight becomes excessive, therefore unexposed portion does not dissolve in developer solution,
Sometimes it is unable to get target pattern.
In general formula (1), as long as the molar ratio of structure shown in structure shown in general formula (2) and general formula (3) is general formula
(2): general formula (3)=90:10~20:80 is just not particularly limited, preferably 80~20:20~80.If being tied shown in general formula (2)
Less than 20, developability becomes inadequate the molar ratio of structure sometimes, if the molar ratio of structure shown in general formula (2) is more than 90, makes
Developability becomes inadequate sometimes when acid value reduces.
In general formula (1), B indicates structure shown in the following general formula (4) independently of each other.
-CO-X(COOH)2-CO-(4)
In general formula (4), X indicates tetrabasic carboxylic acid residue.As tetrabasic carboxylic acid, can enumerate with it is of the invention containing insatiable hunger as first
Substance identical with (c) ingredient of the raw material of the alkali soluble resins of group.They can be used alone, can also share two kinds with
On.
In general formula (1), C indicates structure shown in hydrogen atom or the following general formula (5) independently of each other.
-CO-Y-(COOH)y (5)
In general formula (5), Y indicates 2~4 yuan of polycarboxylic acid residues.As 2~4 yuan of polybasic carboxylic acid, dicarboxyl can be enumerated
Acid, tricarboxylic acids, tetrabasic carboxylic acid.As dicarboxylic acids, tricarboxylic acids, can enumerate and as the first alkali of the invention containing unsaturated group
The identical substance of (d) ingredient of the raw material of soluble resin.As tetrabasic carboxylic acid, can enumerate with it is of the invention containing insatiable hunger as first
Substance identical with (c) ingredient of the raw material of the alkali soluble resins of group.They can be used alone, can also share two kinds with
On.
In general formula (5), y indicates 1~3 integer, preferably expression an integer of 1 or 2.
In general formula (1), l be repeat number average value and independently of each other indicate 0~20, preferably 0~15, more preferably
It is 0~10.If l is more than 20, not only resin viscosity is increased, workability is deteriorated, but also molecular weight becomes excessive, therefore unexposed portion
Insoluble in developer solution, it is unable to get target pattern sometimes.
In general formula (1), m is the average value of repeat number and indicates 1~20, preferably 1~15, more preferably 1~10.If m
More than 20, not only resin viscosity is increased, workability is deteriorated, but also molecular weight becomes excessive, therefore unexposed portion is insoluble in development
Liquid is unable to get target pattern sometimes.
In general formula (1), n indicates that 0~20 integer, preferably 0~10 integer are more preferably 0~4 independently of each other
Integer.If n is more than 20, not only resin viscosity is increased, workability is deteriorated, but also molecular weight becomes excessive, therefore unexposed portion is not
It is dissolved in developer solution, is unable to get target pattern sometimes.
To the acid value (acid of solid component conversion of the first and second alkali soluble resins of the invention containing unsaturated group
Value) be not particularly limited, preferably 100 or less, more preferably 90 or less, further preferably 80 or less, be most preferably 60 with
Under.If acid value is more than 100, electrology characteristic is sometimes insufficient.
The weight average molecular weight of first and second alkali soluble resins of the invention containing unsaturated group is not particularly limited,
Preferably 1,000~50,000,1,000~10,000 are more preferably.If weight average molecular weight is less than 1,000, it some times happens that in advance
The problem of film after baking remains adherency, if more than 50,000, not only resin viscosity increases, workability is deteriorated, Er Qiewei
Exposure portion does not dissolve in developer solution, is unable to get target pattern sometimes.
<<alkali soluble type radiation sensitive resin composition>>
Alkali soluble type radiation sensitive resin composition of the invention is characterized in that, it includes:
(A) first or second alkali soluble resins of the invention containing unsaturated group,
(B) photopolymerization monomer and/or oligomer,
(C) Photoepolymerizationinitiater initiater and
(D) solvent.
<alkali soluble resins of (A) containing unsaturated group>
Alkali soluble resins (being hereinafter also referred to as (A) ingredient) about (A) containing unsaturated group, with first or second sheet
The alkali soluble resins containing unsaturated group of invention is identical.
<(B) photopolymerization monomer and/or oligomer>
It is not particularly limited as (B) photopolymerization monomer and/or oligomer (being hereinafter also referred to as (B) ingredient), it can
With enumerate for example (methyl) acrylic acid -2- hydroxyl ethyl ester, (methyl) 2-hydroxypropyl acrylate, (methyl) acrylic acid -3- hydroxypropyl acrylate,
Ethylene glycol two (methyl) acrylate, diethylene glycol two (methyl) acrylate, triethylene glycol two (methyl) acrylate, tetrem
Glycol two (methyl) acrylate, butanediol two (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, three hydroxyls
Methylpropane two (methyl) acrylate, trimethylolpropane list (methyl) acrylate, trimethylolethane trimethacrylate (methyl) third
Olefin(e) acid ester, trimethylolethane two (methyl) acrylate, trimethylolethane list (methyl) acrylate, pentaerythrite list
(methyl) acrylate, pentaerythrite two (methyl) acrylate, pentaerythrite three (methyl) acrylate, pentaerythrite four
(methyl) acrylate, dipentaerythritol list (methyl) acrylate, dipentaerythritol two (methyl) acrylate, two Ji Wusi
Alcohol three (methyl) acrylate, dipentaerythritol four (methyl) acrylate, dipentaerythritol five (methyl) acrylate, two seasons
Penta tetrol six (methyl) acrylate, glycerol (methyl) acrylate etc..They can be used alone, can also share two kinds with
On.
In alkali soluble type radiation sensitive resin composition of the invention, the content of (B) ingredient is not particularly limited, phase
For 100 parts by weight of (A) ingredient, below preferably 50 parts by weight, it is more preferably 40 parts by weight or less.If content is more than 50 weight
Part, then the adhesiveness after prebake is led to the problem of sometimes.
<(C) Photoepolymerizationinitiater initiater>
It is not particularly limited as (C) Photoepolymerizationinitiater initiater (being hereinafter also referred to as (C) ingredient), it can be cited for example that benzene
Ethyl ketone, 2,2- diethoxy acetophenone, to dimethyl acetophenone, to dimethylamino propiophenone, dichloroacetophenone, trichloro-benzenes second
The acetophenones such as ketone, p-tert.-butyl acetophenone；Benzophenone, 2- chlorobenzophenone, p, bis- dimethylamino benzopheones of p '-etc. two
Benzophenone class；The benzoin ethers such as benzil, benzoin, benzoin methylether, benzoin iso-propylether, benzoin isobutyl ether；It rests in peace
The sulphur compounds such as fragrant double methyl ether, thioxanthene, 2- diuril ton, 2,4- diethyl thioxanthene, 2- methyl thioxanthene, 2- isopropylthioxanthones；2- second
The Anthraquinones such as base anthraquinone, prestox anthraquinone, 1,2 benzae thracene quinone, 2,3- diphenyl anthraquinone；Azodiisobutyronitrile, benzoyl peroxide first
The organic peroxides such as acyl, dicumyl peroxide；2-mercaptobenzimidazole, 2- mercaptobenzoxazole, 2-mercaptobenzothiazole etc.
Mercaptan compound；1,2- acetyl caproyl, 1- [4- (thiophenyl) -, 2- (0- benzoyl oximes)], ethyl ketone, 1- [9- ethyl -6- (2- first
Base benzoyl) -9H- carbazole -3- base] -, the oximes esters such as 1- (0- acetyl group oxime)；Deng.They can be used alone, can also be with
It shares two or more.
In alkali soluble type radiation sensitive resin composition of the invention, the content of (C) ingredient is not particularly limited, phase
For 100 parts by weight of (A) ingredient, preferably 0.1~30 parts by weight, more preferably 1~20 parts by weight.If content is less than 0.1 weight
Part is measured, photopolymerization slows, and sensitivity reduces sometimes, if content is more than 30 parts by weight, light is difficult to reach substrate, thus
The adaptation of substrate and resin is deteriorated sometimes.
<(D) solvent>
It is not particularly limited as (D) solvent (being hereinafter also referred to as (D) ingredient), it can be cited for example that methoxybutyl
Acetic acid esters；The alcohols such as methanol, ethyl alcohol；The ethers such as tetrahydrofuran；Glycol monoethyl ether, glycol dimethyl ether, Ethylene Glycol Methyl second
The glycol ethers such as ether, ethylene glycol monoethyl ether；The ethylene glycol alkyl ethers acetic acid such as methylcellosolve acetate, ethyl cellosolve acetate
Esters；Diethylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol list
The diethylene glycols class such as ether, diethylene glycol monobutyl ether；The propylene glycol such as methyl proxitol acetate, propylene glycol ethyl ether acetic acid esters
Alkylether acetates class；Toluene, dimethylbenzene etc. are aromatic hydrocarbon；Methyl ethyl ketone, methyl amyl ketone, cyclohexanone, 4- hydroxyl -4-
The ketones such as methyl -2 pentanone；And 2 hydroxy propanoic acid ethyl ester, 2- hydroxy-2-methyl methyl propionate, 2- hydroxy-2-methyl propionic acid
Ethyl ester, ethoxy ethyl acetate, hydroxyl ethyl acetate, 2- hydroxy-2-methyl methyl butyrate, 3- methoxy methyl propionate, 3- first
Oxygroup ethyl propionate, 3- ethoxypropanoate, 3- ethoxyl ethyl propionate, ethyl acetate, butyl acetate, methyl lactate, cream
Esters such as acetoacetic ester etc..They can be used alone or in combination with two or more.
In alkali soluble type radiation sensitive resin composition of the invention, the content of (D) ingredient is not particularly limited, though
So changed according to target viscosities, but the solid component concentration of preferably alkali soluble type radiation sensitive resin composition reaches 1
The amount of~50 weight % more preferably reaches the amount of 5~30 weight %.
For alkali soluble type radiation sensitive resin composition of the invention, in addition to above-mentioned (A)~(D) ingredient with
Outside, other compositions can also optionally be contained.It is not particularly limited as other compositions, (E) pigment etc. can be enumerated.They can
To be used alone, can also share two or more.
<(E) pigment>
It is not particularly limited as (E) pigment (being hereinafter also referred to as (E) ingredient), it can be cited for example that carbon black, oxidation
Chromium, iron oxide, titanium be black, nigrosine, Cyanine Black, perylene are black, pigment yellow, paratonere, naphthol green, pigment blue, silica,
Barium titanate, titanium oxide, zirconium oxide, barium sulfate, calcium carbonate etc..They can be used alone or in combination with two or more.
In the case that alkali soluble type radiation sensitive resin composition contains (E) ingredient, its content is not particularly limited,
Relative to 100 parts by weight of (A) ingredient, preferably 50~150 parts by weight, more preferably 80~120 parts by weight.If content is less than 50
Parts by weight, light-proofness is sometimes insufficient, if content is more than 150 parts by weight, the content of original (A) ingredient as binder subtracts
It is few, thus it some times happens that also damaging the undesirable problem of film Forming ability while damaging developing property.
<<cured film>>
Cured film of the invention is characterized in that, is to keep alkali soluble type radiation sensitive resin composition of the invention solid
Made of change.
Cured film of the invention is obtained as alkali soluble type radiation sensitive resin composition of the invention is solidified
Method is not particularly limited, and can enumerate following methods etc.: by infusion process, spray-on process, utilizing slit coater, rotary coating
By in solution coating of alkali soluble type radiation sensitive resin composition to substrate etc., drying carries out any method of machine etc.
After light (including ultraviolet light, radioactive ray etc.) irradiation, development treatment, rear baking are carried out.
The film thickness of cured film of the invention is not particularly limited, preferably 0.1~10 μm, more preferably 0.5~5 μm.
If film thickness is less than 0.1 μm, electrology characteristic is sometimes insufficient, if film thickness is more than 10 μm, is unable to fully solidify when film is integrated with.
The purposes of cured film of the invention is not particularly limited, colour filter, thin film transistor (TFT), liquid crystal display can be enumerated
Protective film or insulating film used in element, integrated circuit component, solid-state imaging element, organic EL etc. or bank material, colour
The solder resist used etc. such as when photoresist, black matrix, printed circuit board manufacture.
<<colour filter>>
Colour filter of the invention is characterized in that it includes cured films of the invention.
<<thin film transistor (TFT)>>
Thin film transistor (TFT) of the invention is characterized in that it includes cured films of the invention.
Embodiment
In the following, enumerating embodiment to illustrate the present invention, but the present invention is not limited to these embodiments.As long as hereinafter, not having
There is special record, then " part " or " % " refers respectively to " parts by weight " or " weight % ".
1. using material
Materials described below has been used in embodiment below and comparative example.
1-1. (a) has epoxy (methyl) acrylate of fluorene skeleton
9,9- bis- (3- methyl -4- hydroxy phenyl) fluorenes type epoxy acrylate (manufacture of Nagase chemteX company)
Bisphenol fluorene type epoxy acrylate (manufacture of Nagase chemteX company)
1-2. (b) does not have epoxy (methyl) acrylate of fluorene skeleton
Bisphenol-a epoxy acrylate (manufacture of Nagase chemteX company)
Triphenol type epoxy acrylate (manufacture of Nagase chemteX company)
Hydrogenated bisphenol A type epoxy acrylate (manufacture of Nagase chemteX company)
1-3. (c) tetrabasic carboxylic acid or its acid dianhydride
3,3 ', 4,4 '-biphenyltetracarboxylic dianhydride pyromellitic dianhydrides
1-4. (d) dicarboxylic acids or tricarboxylic acids or its acid anhydrides
1,2,3,6- tetrabydrophthalic anhydride
1-5. (B) photopolymerization monomer and/or oligomer
Pentaerythrite (three/tetra-) acrylate (manufacture of Daicel-allnex company, PETIA)
1-6. (C) Photoepolymerizationinitiater initiater
Ethyl ketone, 1- [9- ethyl -6- (2- methyl benzoyl) -9H- carbazole -3- base] -, 1- (0- acetyl group oxime)
(BASF AG's manufacture, Irgacure OXE-02)
1-7. (D) solvent
Methoxybutyl acetic acid esters (manufacture of Daicel company)
2. embodiment
(embodiment 1)
By the molar ratio of (a) ingredient and (b) ingredient be (a): in the way of (b)=50:50, in the removable flask of 300ml
Middle mixing is calculated as the first of 9,9- bis- (3- methyl -4- hydroxy phenyl) fluorenes type epoxy acrylate of 51.0g with solid component conversion
Oxygroup butylacetic acid ester solution and with solid component conversion be calculated as 34.7g bisphenol-a epoxy acrylate methoxybutyl
Acetate solution mixes 3,3 ', 4,4 '-biphenyltetracarboxylic dianhydride 5.9g and methoxybutyl acetic acid esters 19.0g later, slowly rises
Temperature is reacted 14 hours at 100~105 DEG C.Later, methoxybutyl acetic acid esters 6.4g is added to be diluted, mixing 1,2,3,6-
Tetrabydrophthalic anhydride 18.4g reacts 4 hours at 90~95 DEG C, obtains alkali soluble resins 1.Obtained alkali soluble resins 1
Solid component be 56.2%, acid value be 48.2mgKOH/g (with solid component conversion be calculated as 85.9mgKOH/g), Weight-average molecular
Amount is 2,100.In addition, l and n are 0, m 1 in general formula (1).
(embodiment 2)
By the molar ratio of (a) ingredient and (b) ingredient be (a): in the way of (b)=50:50, in the removable flask of 300ml
Middle mixing is calculated as the first of 9,9- bis- (3- methyl -4- hydroxy phenyl) fluorenes type epoxy acrylate of 49.6g with solid component conversion
Oxygroup butylacetic acid ester solution and with solid component conversion be calculated as 36.7g triphenol type epoxy acrylate methoxybutyl second
Acid esters solution mixes 3,3 ', 4,4 '-biphenyltetracarboxylic dianhydride 5.8g and methoxybutyl acetic acid esters 15.4g later, slowly rises
Temperature is reacted 14 hours at 100~105 DEG C.Later, methoxybutyl acetic acid esters 5.8g is added to be diluted, mixing 1,2,3,6-
Tetrabydrophthalic anhydride 17.9g reacts 4 hours at 90~95 DEG C, obtains alkali soluble resins 2.Obtained alkali soluble resins 2
Solid component be 55.6%, acid value be 45.6mgKOH/g (with solid component conversion be calculated as 81.9mgKOH/g), Weight-average molecular
Amount is 2,700.In addition, l, m and n are 1 in general formula (1).
(embodiment 3)
By the molar ratio of (a) ingredient and (b) ingredient be (a): in the way of (b)=50:50, in the removable flask of 300ml
Middle mixing is calculated as the first of 9,9- bis- (3- methyl -4- hydroxy phenyl) fluorenes type epoxy acrylate of 49.3g with solid component conversion
Oxygroup butylacetic acid ester solution and with solid component conversion be calculated as 37.1g hydrogenated bisphenol A type epoxy acrylate methoxyl group
Butylacetic acid ester solution mixes 3,3 ', 4,4 '-biphenyltetracarboxylic dianhydride 5.7g and methoxybutyl acetic acid esters 13.3g later, delays
Slow heating, reacts 14 hours at 100~105 DEG C.Later, methoxybutyl acetic acid esters 5.6g is added to be diluted, mixing 1,2,
3,6- tetrabydrophthalic anhydride 17.8g react 4 hours at 90~95 DEG C, obtain alkali soluble resins 3.Obtained alkali solubility
The solid component of resin 3 is 54.8%, and acid value is 47.1mgKOH/g (being calculated as 86.0mgKOH/g with solid component conversion), and weight is equal
Molecular weight is 2,200.In addition, l and n are 0, m 1 in general formula (1).
(embodiment 4)
By the molar ratio of (a) ingredient and (b) ingredient be (a): in the way of (b)=50:50, in the removable flask of 300ml
Middle mixing is calculated as the first of 9,9- bis- (3- methyl -4- hydroxy phenyl) fluorenes type epoxy acrylate of 57.3g with solid component conversion
Oxygroup butylacetic acid ester solution and with solid component conversion be calculated as 38.8g bisphenol-a epoxy acrylate methoxybutyl
Acetate solution mixes 3,3 ', 4,4 '-biphenyltetracarboxylic dianhydride 6.7g and methoxybutyl acetic acid esters 16.7g later, slowly rises
Temperature is reacted 14 hours at 100~105 DEG C.Later, methoxybutyl acetic acid esters 1.0g is added to be diluted, mixing 1,2,3,6-
Tetrabydrophthalic anhydride 6.9g reacts 4 hours at 90~95 DEG C, obtains alkali soluble resins 4.Obtained alkali soluble resins 4
Solid component be 56.5%, acid value be 28.8mgKOH/g (with solid component conversion be calculated as 51.0mgKOH/g), Weight-average molecular
Amount is 2,000.In addition, l and n are 0, m 1 in general formula (1).
(embodiment 5)
By the molar ratio of (a) ingredient and (b) ingredient be (a): in the way of (b)=25:75, in the removable flask of 300ml
Middle mixing is calculated as the first of 9,9- bis- (3- methyl -4- hydroxy phenyl) fluorenes type epoxy acrylate of 32.0g with solid component conversion
Oxygroup butylacetic acid ester solution and with solid component conversion be calculated as 65.4g bisphenol-a epoxy acrylate methoxybutyl
Acetate solution mixes 3,3 ', 4,4 '-biphenyltetracarboxylic dianhydride 7.5g and methoxybutyl acetic acid esters 30.4g later, slowly rises
Temperature is reacted 14 hours at 100~105 DEG C.Later, methoxybutyl acetic acid esters 0.1g is added to be diluted, mixing 1,2,3,6-
Tetrabydrophthalic anhydride 5.1g reacts 4 hours at 90~95 DEG C, obtains alkali soluble resins 5.Obtained alkali soluble resins 5
Solid component be 56.8%, acid value be 25.9mgKOH/g (with solid component conversion be calculated as 45.6mgKOH/g), Weight-average molecular
Amount is 2,000.In addition, l and n are 0, m 1 in general formula (1).
(embodiment 6)
By the molar ratio of (a) ingredient and (b) ingredient be (a): in the way of (b)=50:50, in the removable flask of 300ml
It is middle mixing with solid component conversion be calculated as 59.3g bisphenol fluorene type epoxy acrylate methoxybutyl acetate solution and with
Solid component conversion is calculated as the methoxybutyl acetate solution of the bisphenol-a epoxy acrylate of 38.7g, mixes equal benzene later
Four acid anhydrides 4.9g and methoxybutyl acetic acid esters 18.7g slowly heat up, and react 14 hours at 100~105 DEG C.Later, first is added
Oxygroup butylacetic acid ester 1.2g is diluted, and mixes 1,2,3,6- tetrabydrophthalic anhydride 6.9g, small in 90~95 DEG C of reactions 4
When, obtain alkali soluble resins 6.The solid component of obtained alkali soluble resins 6 be 55.9%, acid value be 29.7mgKOH/g (with
Solid component conversion is calculated as 53.2mgKOH/g), weight average molecular weight 2,100.In addition, l and n are 0, m 1 in general formula (1).
(embodiment 7)
By the molar ratio of (a) ingredient and (b) ingredient be (a): in the way of (b)=50:50, in the removable flask of 300ml
It is middle mixing with solid component conversion be calculated as 60.3g bisphenol fluorene type epoxy acrylate methoxybutyl acetate solution and with
Solid component conversion is calculated as the methoxybutyl acetate solution of the bisphenol-a epoxy acrylate of 39.4g, mixes equal benzene later
Four acid anhydrides 10.0g and methoxybutyl acetic acid esters 10.4g slowly heat up, and react 14 hours at 100~105 DEG C.Later, it is added
Methoxybutyl acetic acid esters 8.2g is diluted, and obtains alkali soluble resins 7.The solid component of obtained alkali soluble resins 7 is
55.6%, acid value is 28.9mgKOH/g (being calculated as 52.0mgKOH/g with solid component conversion), weight average molecular weight 2,900.Separately
Outside, in general formula (1), l and n are 0, m 1.
(comparative example 1)
(3- methyl -4- the hydroxyl of 9,9- bis- that 75.4g is calculated as with solid component conversion is mixed in the removable flask of 300ml
Phenyl) fluorenes type epoxy acrylate methoxybutyl acetate solution and 3,3 ', 4,4 '-biphenyltetracarboxylic dianhydride 8.7g and first
Oxygroup butylacetic acid ester 0.3g slowly heats up, and reacts 14 hours at 100~105 DEG C.Later, methoxybutyl acetic acid esters is added
16.4g is diluted, and mixes 1,2,3,6- tetrabydrophthalic anhydride 25.8g, is reacted 4 hours at 90~95 DEG C, is obtained alkali soluble
Property resin 8.The solid component of obtained alkali soluble resins 8 is 56.0%, and acid value is that 73.7mgKOH/g (is changed with solid component
Calculate for 131.6mgKOH/g), weight average molecular weight 2,300.
(comparative example 2)
The bisphenol fluorene type epoxy acrylate that 88.3g is calculated as with solid component conversion is mixed in the removable flask of 300ml
Methoxybutyl acetate solution and 3,3 ', 4,4 '-biphenyltetracarboxylic dianhydride 12.9g and methoxybutyl acetic acid esters 2.9g,
Slowly heating is reacted 14 hours at 100~105 DEG C.Later, methoxybutyl acetic acid esters 23.1g is added to be diluted, mixing 1,
2,3,6- tetrabydrophthalic anhydride 8.9g react 4 hours at 90~95 DEG C, obtain alkali soluble resins 9.Obtained alkali solubility
The solid component of resin 9 is 55.2%, and acid value is 48.5mgKOH/g (being calculated as 87.9mgKOH/g with solid component conversion), and weight is equal
Molecular weight is 2,300.
(comparative example 3)
The bisphenol fluorene type epoxy acrylate that 96.1g is calculated as with solid component conversion is mixed in the removable flask of 300ml
Methoxybutyl acetate solution and 3,3 ', 4,4 '-biphenyltetracarboxylic dianhydride 14.0g and methoxybutyl acetic acid esters 3.1g,
Slowly heating is reacted 14 hours at 100~105 DEG C.Later, methoxybutyl acetic acid esters 17.3g is added to be diluted, obtains alkali
Soluble resin 10.The solid component of obtained alkali soluble resins 10 be 55.9%, acid value be 30.1mgKOH/g (with solid at
Conversion is divided to be calculated as 53.9mgKOH/g), weight average molecular weight 2,200.
(mixed example 1~7 and more mixed example 1~3)
Using alkali soluble resins 1~10 obtained in Examples 1 to 7 and comparative example 1~3, with weight shown in following table 1
Than mixing each ingredient, alkali soluble type radiation sensitive resin composition is obtained.For obtained alkali soluble type radiation-sensitive
Resin combination evaluates alkali solubility, development adaptation, resolution ratio, electrology characteristic by following methods.Wherein, about mixed example
2,3,5~7 and more mixed example 3 obtained in alkali soluble type radiation sensitive resin composition, do not evaluate electrology characteristic.It will knot
Fruit is shown in following table 1.
3. evaluation method
3-1. alkali solubility
By be not exposed processing, at 90 DEG C be impregnated into 0.1 with 2 μm of 2 minutes film thickness of heating plate prebake of film
In the potassium hydroxide aqueous solution of weight %, the time required for measurement film dissolves, thus in accordance with following three Phase Evaluation alkali
Dissolubility.
Zero: the good situation of alkali solubility (film dissolution time was less than 60 seconds)
△: the bad situation of alkali solubility (film dissolution time was 60 seconds more than and less than 300 seconds)
×: the bad situation of alkali solubility (film dissolution time is 300 or more)
3-2. development adaptation
For with 2 μm of 2 minutes film thickness of heating plate prebake of film, passing through ultra high pressure mercury using negative mask at 90 DEG C
Lamp is with 100mJ/cm2After being exposed processing, dipping makes above-mentioned alkali-soluble comment in the potassium hydroxide aqueous solution of 0.1 weight %
The time that film dissolution time obtained in valence is 1.2 times, develop, the glass substrate after development is amplified 50 times, visually
Line pattern is confirmed, thus in accordance with following three Phase Evaluations development adaptation.
Zero: the good situation (not from strippable substrate, being formed with line pattern) of development adaptation
△: the bad situation (although foring line pattern, pattern defect has occurred) of development adaptation
×: the bad situation of development adaptation (from strippable substrate, not formed line pattern)
3-3. resolution ratio
For with 2 μm of 2 minutes film thickness of heating plate prebake of film, passing through ultra high pressure mercury using negative mask at 90 DEG C
Lamp is with 100mJ/cm2After being exposed processing, dipping makes above-mentioned alkali-soluble comment in the potassium hydroxide aqueous solution of 0.1 weight %
The time that film dissolution time obtained in valence is 1.2 times, develop, the glass substrate after development is amplified 500 times, visually
Line pattern is confirmed, thus in accordance with following three Phase Evaluation resolution ratio.
Zero: the good situation of resolution ratio (resolution ratio is less than 30 μm)
△: the bad situation of resolution ratio (resolution ratio is 30 μm more than and less than 100 μm)
×: the bad situation of resolution ratio (resolution ratio is 100 μm or more)
3-4. electrology characteristic
For at 90 DEG C with 0.5 μm of 2 minutes film thickness of heating plate prebake of film, using ultrahigh pressure mercury lamp with 100mJ/
cm2It after being exposed processing, is baked after ten minutes at 200 DEG C with baking oven, uses 2400 type (Keithley of source table
The manufacture of Instruments company) measurement current-voltage characteristic, the evaluation of the leakage current of obtained film is carried out, thus in accordance with
Following three Phase Evaluation electrology characteristics.
Zero: the good situation of electrology characteristic (leakage current is small)
△: the bad situation of electrology characteristic (leakage current is slightly larger)
×: the bad situation of electrology characteristic (leakage current is big)
[table 1]
As shown in Table 1, the mixed example 1 for the alkali soluble resins for sharing (a) ingredient and (b) ingredient has been used
In~7, mixed example 1~3 is compared compared with having used the alkali soluble resins merely with (a) ingredient, although acid value is low, alkali soluble
Property, development adaptation, excellent in resolution, in addition, especially in mixed example 4, electrical characteristic is also excellent.
Claims (11)
1. a kind of alkali soluble resins containing unsaturated group, which is characterized in that it is
(a) with fluorene skeleton epoxy (methyl) acrylate,
(b) without fluorene skeleton epoxy (methyl) acrylate and
(c) reactant of tetrabasic carboxylic acid or its acid dianhydride.
2. being containing the alkali soluble resins of unsaturated group as described in claim 1
(a) with fluorene skeleton epoxy (methyl) acrylate,
(b) without fluorene skeleton epoxy (methyl) acrylate,
(c) tetrabasic carboxylic acid or its acid dianhydride and
(d) reactant of dicarboxylic acids or tricarboxylic acids or its acid anhydrides.
3. as claimed in claim 1 or 2 containing the alkali soluble resins of unsaturated group, wherein (b) ingredient has cyclic structure.
4. a kind of alkali soluble resins containing unsaturated group, which is characterized in that its by the following general formula (1) indicate,
[changing 1]
In general formula (1), A indicates structure shown in the following general formula (2) or (3) independently of each other, structure shown in general formula (2) and logical
The molar ratio of structure shown in formula (3) is general formula (2): general formula (3)=90:10~20:80, and B indicates following logical independently of each other
Structure shown in formula (4), C indicate structure shown in hydrogen atom or the following general formula (5) independently of each other, and l is being averaged for repeat number
Value and independently of each other 0~20, m of expression are the average value of repeat number and indicate that 1~20, n indicates 0~20 independently of each other
Integer,
[changing 2]
In general formula (2), D indicates to remove epoxy (methyl) acrylate position from epoxy (methyl) acrylate with fluorene skeleton
Bivalent group afterwards, R1Hydrogen atom or methyl are indicated independently of each other,
[changing 3]
In general formula (3), E indicates to remove epoxy (methyl) acrylate portion from epoxy (methyl) acrylate for not having fluorene skeleton
Multivalence group behind position, R1Indicate that hydrogen atom or methyl, n indicate 0~20 integer independently of each other,
-CO-X(COOH)2-CO- (4)
In general formula (4), X indicates tetrabasic carboxylic acid residue,
-CO-Y-(COOH)y (5)
In general formula (5), Y indicates that 2~4 yuan of polycarboxylic acid residues, y indicate 1~3 integer.
5. as claimed in claim 4 containing the alkali soluble resins of unsaturated group, wherein in general formula (2), D indicates following logical
Structure shown in formula (6),
[changing 4]
In general formula (6), R2Hydrogen atom is indicated independently of each other, alkyl, phenyl or the halogen group that carbon atom number is 1~5, k is indicated
0~10 integer.
6. as described in claim 4 or 5 containing the alkali soluble resins of unsaturated group, wherein in general formula (1), C indicates general formula
(5) structure shown in, and in general formula (5), Y indicates that 2 yuan or 3 yuan of polycarboxylic acid residues, y indicate an integer of 1 or 2.
7. acid value is 100 or less such as the alkali soluble resins according to any one of claims 1 to 6 containing unsaturated group.
8. a kind of alkali soluble type radiation sensitive resin composition, which is characterized in that it includes:
(A) alkali soluble resins according to any one of claims 1 to 7 containing unsaturated group,
(B) photopolymerization monomer and/or oligomer,
(C) Photoepolymerizationinitiater initiater and
(D) solvent.
9. a kind of cured film, which is characterized in that it is to make alkali soluble type radiation sensitive resin composition according to any one of claims 8
Made of solidification.
10. a kind of colour filter, which is characterized in that it includes cured films as claimed in claim 9.
11. a kind of thin film transistor (TFT), which is characterized in that it includes cured films as claimed in claim 9.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2016-210642 | 2016-10-27 | ||
| JP2016210642A JP2018070724A (en) | 2016-10-27 | 2016-10-27 | Unsaturated group-containing alkali-soluble resin and alkali-soluble radiation-sensitive resin composition |
| PCT/JP2017/037668 WO2018079368A1 (en) | 2016-10-27 | 2017-10-18 | Unsaturated-group-containing alkali-soluble resin, and alkali-soluble radiation-sensitive resin composition |
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| Publication Number | Publication Date |
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| CN109715698A true CN109715698A (en) | 2019-05-03 |
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ID=62024902
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|---|---|---|---|
| CN201780056482.4A Pending CN109715698A (en) | 2016-10-27 | 2017-10-18 | Alkali soluble resins and alkali soluble type radiation sensitive resin composition containing unsaturated group |
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| Country | Link |
|---|---|
| JP (1) | JP2018070724A (en) |
| KR (1) | KR20190075907A (en) |
| CN (1) | CN109715698A (en) |
| TW (1) | TW201821466A (en) |
| WO (1) | WO2018079368A1 (en) |
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| JPH09304929A (en) * | 1996-05-10 | 1997-11-28 | Nippon Steel Chem Co Ltd | Alkali developable photosensitive resin composition |
| TW200530281A (en) * | 2003-11-26 | 2005-09-16 | Nippon Steel Chemical Co | Photosensitive resin composition and color filter using the same |
| TW200902579A (en) * | 2007-07-04 | 2009-01-16 | Tokyo Ohka Kogyo Co Ltd | Colored photosensitive composition |
| CN101845137A (en) * | 2009-03-25 | 2010-09-29 | 新日铁化学株式会社 | Alkaline water-soluble resin, its producing method and photosensitive resin composition using same |
| CN102414616A (en) * | 2009-04-27 | 2012-04-11 | 日产化学工业株式会社 | Photosensitive composition using photopolymerizable polymer having fluorene skeleton |
| CN103980472A (en) * | 2014-05-27 | 2014-08-13 | 张家港康得新光电材料有限公司 | Epoxy acrylate low polymer containing fluorene as well as preparation method and application thereof |
| JP2015127730A (en) * | 2013-12-27 | 2015-07-09 | 新日鉄住金化学株式会社 | Black photosensitive composition for touch panel, cured product thereof, and touch panel including the cured product |
| CN104849960A (en) * | 2014-02-13 | 2015-08-19 | 奇美实业股份有限公司 | Resin, photosensitive resin composition, optical filter and its manufacturing method, liquid crystal display device |
| CN105467761A (en) * | 2014-09-30 | 2016-04-06 | 新日铁住金化学株式会社 | Photosensitive resin composition used for touch screen, and hardening film thereof, and touch screen with hardening film |
| CN107531880A (en) * | 2015-04-28 | 2018-01-02 | 长濑化成株式会社 | Alkali soluble resins |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3268771B2 (en) | 2000-06-12 | 2002-03-25 | ナガセケムテックス株式会社 | Photopolymerizable unsaturated compound, method for producing the same, and alkali-soluble radiation-sensitive resin composition using the same |
| JP4489564B2 (en) * | 2003-11-26 | 2010-06-23 | 新日鐵化学株式会社 | Photosensitive resin composition and color filter using the same |
-
2016
- 2016-10-27 JP JP2016210642A patent/JP2018070724A/en active Pending
-
2017
- 2017-10-18 WO PCT/JP2017/037668 patent/WO2018079368A1/en active Application Filing
- 2017-10-18 KR KR1020197009064A patent/KR20190075907A/en unknown
- 2017-10-18 CN CN201780056482.4A patent/CN109715698A/en active Pending
- 2017-10-23 TW TW106136288A patent/TW201821466A/en unknown
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09304929A (en) * | 1996-05-10 | 1997-11-28 | Nippon Steel Chem Co Ltd | Alkali developable photosensitive resin composition |
| TW200530281A (en) * | 2003-11-26 | 2005-09-16 | Nippon Steel Chemical Co | Photosensitive resin composition and color filter using the same |
| TW200902579A (en) * | 2007-07-04 | 2009-01-16 | Tokyo Ohka Kogyo Co Ltd | Colored photosensitive composition |
| CN101845137A (en) * | 2009-03-25 | 2010-09-29 | 新日铁化学株式会社 | Alkaline water-soluble resin, its producing method and photosensitive resin composition using same |
| CN102414616A (en) * | 2009-04-27 | 2012-04-11 | 日产化学工业株式会社 | Photosensitive composition using photopolymerizable polymer having fluorene skeleton |
| JP2015127730A (en) * | 2013-12-27 | 2015-07-09 | 新日鉄住金化学株式会社 | Black photosensitive composition for touch panel, cured product thereof, and touch panel including the cured product |
| CN104849960A (en) * | 2014-02-13 | 2015-08-19 | 奇美实业股份有限公司 | Resin, photosensitive resin composition, optical filter and its manufacturing method, liquid crystal display device |
| CN103980472A (en) * | 2014-05-27 | 2014-08-13 | 张家港康得新光电材料有限公司 | Epoxy acrylate low polymer containing fluorene as well as preparation method and application thereof |
| CN105467761A (en) * | 2014-09-30 | 2016-04-06 | 新日铁住金化学株式会社 | Photosensitive resin composition used for touch screen, and hardening film thereof, and touch screen with hardening film |
| CN107531880A (en) * | 2015-04-28 | 2018-01-02 | 长濑化成株式会社 | Alkali soluble resins |
Also Published As
| Publication number | Publication date |
|---|---|
| TW201821466A (en) | 2018-06-16 |
| KR20190075907A (en) | 2019-07-01 |
| JP2018070724A (en) | 2018-05-10 |
| WO2018079368A1 (en) | 2018-05-03 |
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