JP2022528671A - ヘキサアリールビスイミダゾール類光開始剤及びその使用 - Google Patents
ヘキサアリールビスイミダゾール類光開始剤及びその使用 Download PDFInfo
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- JP2022528671A JP2022528671A JP2021558511A JP2021558511A JP2022528671A JP 2022528671 A JP2022528671 A JP 2022528671A JP 2021558511 A JP2021558511 A JP 2021558511A JP 2021558511 A JP2021558511 A JP 2021558511A JP 2022528671 A JP2022528671 A JP 2022528671A
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- Prior art keywords
- meth
- photosensitive resin
- compound
- group
- acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000011342 resin composition Substances 0.000 claims abstract description 70
- 125000001424 substituent group Chemical group 0.000 claims abstract description 56
- -1 benzyl compound Chemical class 0.000 claims description 122
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 96
- 150000001875 compounds Chemical class 0.000 claims description 72
- 239000011347 resin Substances 0.000 claims description 51
- 229920005989 resin Polymers 0.000 claims description 51
- 229920000642 polymer Polymers 0.000 claims description 37
- 150000003934 aromatic aldehydes Chemical class 0.000 claims description 24
- 238000000576 coating method Methods 0.000 claims description 24
- 239000011248 coating agent Substances 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 21
- 239000004020 conductor Substances 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 17
- 238000007363 ring formation reaction Methods 0.000 claims description 15
- 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 claims description 14
- 238000007254 oxidation reaction Methods 0.000 claims description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 13
- 230000001681 protective effect Effects 0.000 claims description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000000852 hydrogen donor Substances 0.000 claims description 10
- 239000004065 semiconductor Substances 0.000 claims description 9
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- RKYJPYDJNQXILT-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxycarbonyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OCCOC(=O)C=C RKYJPYDJNQXILT-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
- 239000004973 liquid crystal related substance Substances 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000004014 plasticizer Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 238000004040 coloring Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 150000002898 organic sulfur compounds Chemical class 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 claims description 3
- 150000003077 polyols Chemical class 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims description 2
- WABPQHHGFIMREM-UHFFFAOYSA-N lead(0) Chemical compound [Pb] WABPQHHGFIMREM-UHFFFAOYSA-N 0.000 claims description 2
- 150000003021 phthalic acid derivatives Chemical class 0.000 claims description 2
- 229920000180 alkyd Polymers 0.000 claims 1
- 238000011161 development Methods 0.000 abstract description 23
- 206010034972 Photosensitivity reaction Diseases 0.000 abstract description 14
- 230000036211 photosensitivity Effects 0.000 abstract description 14
- 239000000203 mixture Substances 0.000 abstract description 11
- 239000010802 sludge Substances 0.000 abstract description 6
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 238000010586 diagram Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 48
- 239000010410 layer Substances 0.000 description 38
- 239000010408 film Substances 0.000 description 32
- 238000000034 method Methods 0.000 description 31
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 26
- 239000001294 propane Substances 0.000 description 25
- 239000000758 substrate Substances 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 238000007747 plating Methods 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- AZUHIVLOSAPWDM-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1h-imidazole Chemical compound C1=CNC(C=2NC=CN=2)=N1 AZUHIVLOSAPWDM-UHFFFAOYSA-N 0.000 description 10
- 238000010030 laminating Methods 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 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 8
- FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical group ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 8
- 238000005530 etching Methods 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 229910019142 PO4 Inorganic materials 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 239000012634 fragment Substances 0.000 description 7
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 7
- 239000010452 phosphate Substances 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 6
- 244000028419 Styrax benzoin Species 0.000 description 6
- 235000000126 Styrax benzoin Nutrition 0.000 description 6
- 235000008411 Sumatra benzointree Nutrition 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- 235000019382 gum benzoic Nutrition 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 6
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 6
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- 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 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- 239000002699 waste material Substances 0.000 description 5
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 4
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 4
- 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 4
- MHRDCHHESNJQIS-UHFFFAOYSA-N 2-methyl-3-sulfanylpropanoic acid Chemical compound SCC(C)C(O)=O MHRDCHHESNJQIS-UHFFFAOYSA-N 0.000 description 4
- PMNLUUOXGOOLSP-UHFFFAOYSA-M 2-sulfanylpropanoate Chemical compound CC(S)C([O-])=O PMNLUUOXGOOLSP-UHFFFAOYSA-M 0.000 description 4
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- OAZWDJGLIYNYMU-UHFFFAOYSA-N Leucocrystal Violet Chemical compound C1=CC(N(C)C)=CC=C1C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 OAZWDJGLIYNYMU-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229960002130 benzoin Drugs 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 230000001678 irradiating effect Effects 0.000 description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000005070 sampling Methods 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- GMIUUCWUOPOETN-UHFFFAOYSA-N 2,4,5-triphenyl-1-(2,4,5-triphenylimidazol-2-yl)imidazole Chemical compound C1=CC=CC=C1C1=NC(N2C(=C(N=C2C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C=CC=CC=2)(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 GMIUUCWUOPOETN-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- JTMBCYAUSCBSEY-UHFFFAOYSA-N 2-methyl-2-sulfanylpropanoic acid Chemical compound CC(C)(S)C(O)=O JTMBCYAUSCBSEY-UHFFFAOYSA-N 0.000 description 3
- RQPNXPWEGVCPCX-UHFFFAOYSA-N 3-sulfanylbutanoic acid Chemical compound CC(S)CC(O)=O RQPNXPWEGVCPCX-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 3
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 150000004775 coumarins Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Natural products CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000007772 electroless plating Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 229910052737 gold Inorganic materials 0.000 description 3
- 239000010931 gold Substances 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229910000679 solder Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000010345 tape casting Methods 0.000 description 3
- 150000003918 triazines Chemical class 0.000 description 3
- 150000003673 urethanes Chemical class 0.000 description 3
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- OGVRJXPGSVLDRD-UHFFFAOYSA-N 2,3-dimethylanthracene Chemical compound C1=CC=C2C=C(C=C(C(C)=C3)C)C3=CC2=C1 OGVRJXPGSVLDRD-UHFFFAOYSA-N 0.000 description 2
- YSFBEAASFUWWHU-UHFFFAOYSA-N 2,4-dichlorobenzaldehyde Chemical group ClC1=CC=C(C=O)C(Cl)=C1 YSFBEAASFUWWHU-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical group CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JEVGKYBUANQAKG-UHFFFAOYSA-N victoria blue R Chemical compound [Cl-].C12=CC=CC=C2C(=[NH+]CC)C=CC1=C(C=1C=CC(=CC=1)N(C)C)C1=CC=C(N(C)C)C=C1 JEVGKYBUANQAKG-UHFFFAOYSA-N 0.000 description 1
- ROVRRJSRRSGUOL-UHFFFAOYSA-N victoria blue bo Chemical compound [Cl-].C12=CC=CC=C2C(NCC)=CC=C1C(C=1C=CC(=CC=1)N(CC)CC)=C1C=CC(=[N+](CC)CC)C=C1 ROVRRJSRRSGUOL-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- 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
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
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Abstract
Description
(1)一般式(I)で表される芳香族アルデヒドと一般式(II)で表される芳香族アルデヒドは、縮合、酸化反応により、ベンジル類化合物を得た。このベンジル類化合物と一般式(III)で表される芳香族アルデヒドは、環形成反応により、モノイミダゾール化合物Mを生成した。
(2)一般式(IV)で表される芳香族アルデヒドと一般式(V)で表される芳香族アルデヒドは、縮合、酸化反応により、ベンジル類化合物を得た。このベンジル類化合物と一般式(VI)で表される芳香族アルデヒドは、環形成反応により、ノイミダゾール化合物Nを生成した。
(3)モノイミダゾール化合物MとNは、酸化反応により、ヘキサアリールビスイミダゾール類光開始剤を生成した。
上記のように、本発明のヘキサアリールビスイミダゾール類光開始剤、以下のステップによって調製された。
(1)一般式(I)で表される芳香族アルデヒドと一般式(II)で表される芳香族アルデヒドは、縮合、酸化反応により、ベンジル類化合物を得た。このベンジル類化合物と一般式(III)で表される芳香族アルデヒドは、環形成反応により、モノイミダゾール化合物Mを生成した。
(2)一般式(IV)で表される芳香族アルデヒドと一般式(V)で表される芳香族アルデヒドは、縮合、酸化反応により、ベンジル類化合物を得た。このベンジル類化合物と一般式(VI)で表される芳香族アルデヒドは、環形成反応により、モノイミダゾール化合物Nを生成した。
(3)モノイミダゾール化合物MとNは、酸化反応により、ヘキサアリールビスイミダゾール類光開始剤を生成した。
(1)amolの一般式(I)で表される芳香族アルデヒド(R1-R5における赤方偏移置換基の数が、Aであり)とbmolの一般式(II)で表される芳香族アルデヒド(R6-R10における赤方偏移置換基の数が、Bであり)は、縮合、酸化反応により、(a+b)/2molのベンジル類化合物を得た。このベンジル類化合物と(a+b)/2molの一般式(III)で表される芳香族アルデヒド(R11-R15における赤方偏移置換基の数が、Cであり)は、環形成反応により、モノイミダゾール化合物Mを生成し、Mにおける赤方偏移置換基の数が、mである。
(2)a’molの一般式(IV)で表される芳香族アルデヒド(R16-R20における赤方偏移置換基の数が、A’であり)とb’molの一般式(V)で表される芳香族アルデヒド(R21-R25における赤方偏移置換基の数が、B’であり)は、縮合、酸化反応により、(a’+b’)/2molのベンジル類化合物を得た。このベンジル類化合物と(a’+b’)/2molの一般式(VI)で表される芳香族アルデヒド(R26-R30における赤方偏移置換基の数が、C’であり)は、環形成反応によりモノイミダゾール化合物Nを生成し、Nにおける赤方偏移置換基の数は、nである。
(3)emolのモノイミダゾール化合物Mとfmolのモノイミダゾール化合物Nは、酸化反応により、ヘキサアリールビスイミダゾール類光開始剤を生成し、赤方偏移置換基は、ヘキサアリールビスイミダゾール類光開始剤の全ての置換可能なサイト(即ち、R1-R30)におけるモル比が、pである。
上記のように、本発明のヘキサアリールビスイミダゾール類光開始剤は、感光性樹脂組成物に使用された場合に優れた性能を有する。したがって、それに応じて、本発明はまた、以下の成分を含むことを特徴とする感光性樹脂組成物を提供する。
(A)前記のようなヘキサアリールビスイミダゾール類光開始剤、
(B)アルカリ可溶性ポリマー、
(C)エチレン性不飽和二重結合を有する化合物、
(D)水素供与体、
(E)他の任意の助剤。
上記のような特徴的な制限範囲内で、本発明のヘキサアリールビスイミダゾール類光開始剤について、ビスイミダゾールに対する接続位置を制限しない。 例示的に、前記ヘキサアリールビスイミダゾール類光開始剤は、以下の化合物のうちの少なくとも1つから選択されるか、またはそれらを含むことができる。
(1)1molベンズアルデヒド与1molo-クロロベンズアルデヒドは、自己縮合、酸化反応により、1molのベンジル類化合物を得た。このベンジル類化合物と1molのo-クロロベンズアルデヒドは、環形成反応により、モノイミダゾール化合物M1を生成し、M1における赤方偏移置換基の数が、2である。
(2)2molのベンズアルデヒドを自身縮合、酸化反応することにより、1molのベンジル類化合物を得た。このベンジル類化合物と1molo-クロロベンズアルデヒドは、環形成反応により、モノイミダゾール化合物N1を生成し、N1における赤方偏移置換基の数が、1である。
(3)1molモノイミダゾール化合物M1と1molモノイミダゾール化合物N1は酸化反応により、ヘキサアリールビスイミダゾール類光開始剤を生成し、ヘキサアリールビスイミダゾール類光開始剤の全ての置換可能なサイトにおける赤方偏移置換基のモル比が、10%である。
1molのモノイミダゾール化合物M1と9molのモノイミダゾール化合物Nは、酸化反応により、ヘキサアリールビスイミダゾール類光開始剤を生成し、ヘキサアリールビスイミダゾール類光開始剤の全ての置換可能なサイトにおける赤方偏移置換基のモル比が、7.3%である。
9molのモノイミダゾール化合物M1と1molのモノイミダゾール化合物N1は、酸化反応により、ヘキサアリールビスイミダゾール類光開始剤を生成し、ヘキサアリールビスイミダゾール類光開始剤の全ての置換可能なサイトにおける赤方偏移置換基のモル比が、12.7%である。
(1)1molp-メチルベンズアルデヒドと1molo-クロロベンズアルデヒドを縮合、酸化反応して、1molのベンジル類化合物を得た。このベンジル類化合物と1molの2,4-ジクロロベンズアルデヒドは、環形成反応により、モノイミダゾール化合物M2を生成し、M2における赤方偏移置換基の数が、3である。
(2)1molのモノイミダゾール化合物M2と1molのモノイミダゾール化合物N1は、酸化反応により、ヘキサアリールビスイミダゾール類光開始剤を生成し、ヘキサアリールビスイミダゾール類光開始剤の全ての置換可能なサイトにおける赤方偏移置換基のモル比が、13.3%である。
2molのモノイミダゾール化合物M2と1molのモノイミダゾール化合物N1は、酸化反応によりヘキサアリールビスイミダゾール類光開始剤を生成し、ヘキサアリールビスイミダゾール類光開始剤の全ての置換可能なサイトにおける赤方偏移置換基のモル比が、15.6%である。
(1)1molのp-メチルベンズアルデヒドと1molのベンズアルデヒドを縮合、酸化反応して、1molのベンジル類化合物を得た。このベンジル類化合物と1molのo-クロロベンズアルデヒドは、環形成反応によりモノイミダゾール化合物M3を生成し、M3における赤方偏移置換基の数が、1である。
(2)2molのモノイミダゾール化合物M3は、自己酸化反応により、ヘキサアリールビスイミダゾール類光開始剤を生成し、ヘキサアリールビスイミダゾール類光開始剤の全ての置換可能なサイトにおける赤方偏移置換基のモル比が、6.7%である。
アルカリ可溶性ポリマーは、感光性樹脂組成物に皮膜形成機能を与えることができる。アルカリ可溶性ポリマーとして、このような特性を有する重合体であれば、特に制限なく使用できる。
エチレン性不飽和二重結合を有する化合物は、感光性樹脂組成物の成膜を促進することができる。
本発明の感光性樹脂組成物は、感光度を向上させるために水素供与体をさらに含む。ビスイミダゾール類化合物は、光照で分解され、生成されるモノイミダゾールラジカルは体積が大きく、立体障害効果により活性が低下し、単量体重合を単独で開始することは困難であり、水素供与体と組み合わせて使用すると、モノイミダゾールラジカルは容易に水素供与体から活性水素を取り除き、新たな活性ラジカルが生まれ、単量体重合を開始する。
上記の各成分に加えて、本発明の感光性樹脂組成物には、任意的に、必要に応じて、適量の他の助剤を更に含むことができる。例えば、助剤は、他の光開始剤及び/又は増感剤、有機溶媒、染料、顔料、光発色剤、充填剤、可塑剤、安定剤、コーティング助剤、剥離促進剤等の少なくとも一種を含むことができる。
本発明の感光性樹脂組成物は、ドライフィルムに製造して、即ち、感光性樹脂積層体の形で、プリント回路板、保護パターン、導体パターン、リード線、半導体パッケージの製造に使用することができ、各々の工程を経て異なる基材に必要なパターンを形成できる。
本発明のドライフィルム、即ち、感光性樹脂積層体は、感光性樹脂組成物から形成される感光性樹脂層、及び当該感光性樹脂層を支持する支持体を含む。
(1)感光性樹脂積層体を銅張積層板又はフレキシブル基板に積層する積層工程と、
(2)感光性樹脂積層体における感光性樹脂層を露光し、画像状に活性光線を照射し、露光された部分を光硬化させる露光工程と、
(3)感光性樹脂層の露光されてない部分を現像液で除去して保護パターンを形成する現像工程と、
(4):保護パターンで覆われていない銅張積層板又はフレキシブル基板の表面の部分に対してエッチングまたはめっきする導体パターン形成工程と、
(5)保護パターンを該銅張積層板又はフレキシブル基板から剥離する剥離工程、を含むプリント回路板の製造における前記ドライフィルムの使用を提供する。
本発明の感光性樹脂組成物は、ウェットフィルムの形で直接に基板に塗布して、プリント回路板、保護パターン、導体パターン、リード線、半導体パッケージ等の製造に使用することができる。
本発明は、カラーフィルタの製造における上記の感光性樹脂組成物の使用、カラーフィルタ及びカラーフィルタを有する液晶ディスプレイモジュールに関する。
感光性樹脂層形成工程は、支持体上に本発明の感光性樹脂組成物を塗布して感光性樹脂層を形成することである。
露光工程は、上記の感光性樹脂層形成工程で形成された感光性樹脂層をマスクにより露光し、光照射されたコーティング膜の一部のみを硬化させることである。
露光工程の後にアルカリ性現像処理(現像工程)を行い、露光工程における未露光部をアルカリ性水溶液に溶かす。その結果、光硬化部分のみが残る。
1.1ヘキサアリールビスイミダゾール類光開始剤a1
1.1.1モノイミダゾール化合物a1-3の調製
1Lの4つ口フラスコに66gビタミンB1、195g純水及び195gエタノールを加え、攪拌を開始し、氷浴で内温0-10℃に冷却し、10%NaOH水溶液99gを滴下し、約20分間で滴下が完了し、この時のpHは8-9である。その後、75gベンズアルデヒド(0.7mol)及びo-クロロベンズアルデヒド99g(0.7mol)の混合溶液を滴下し、約40分間で滴下が完了し、内温65℃に昇温し、保温反応(この期間、pHが8-9になるように、10%NaOH水溶液を追加する。)を行う。サンプリングして、HPLCによって、ベンズアルデヒドとo-クロロベンズアルデヒドがいずれも1%未満に制御し、保温を終了し、水層を分離した。最初に、それを200g純水で1回洗浄し、次に10%NaHSO3100mL水溶液で1回洗浄し、最後に200g純水で2回洗浄して、156g茶色の液体a1-1を得た。
a1-3の調製工程を参照してINCを調製し、2molベンズアルデヒドが自己縮合、酸化反応により、1molのベンジル類化合物を得り、このベンジル類化合物とo-クロロベンズアルデヒド1molが環形成反応によりモノイミダゾール化合物INCを生成するという点で異なる。LCMSを使用してINC構造を確認し、質量分析で機器に付属のソフトウェアを使用して311と312の分子フラグメントピークを取得し、製品INCの分子量が330であり、T+1とT+2と一致している。
窒素ガスの保護で、500mLの4つ口フラスコに13.0gの黄色の固体a1-3(0.036mol)、11.9gの2-(o-クロロフェニル)-4,5-ジフェニル-イミダゾール(INC)(0.036mol)、0.5gの30%液体苛性ソーダ、0.5gの臭化テトラブチルアンモニウム及び100gのトルエンを投げ込み、加熱して攪拌し、内部温度が60-65℃時に40gの次亜塩素酸ナトリウム(11%水溶液)を滴下し、滴下後に反応温度を維持し、サンプリングして、HPLCによって制御し、a1-3とINCがいずれも1%未満であると、反応が完了し、保温を終了する。保温反応終了後、純水50gで4回洗浄、更にトルエン20gで水層を1回抽出し、その後、上記抽出で得られた有機層を減圧下で蒸留して、蒸留で得られるものにメタノール20gを加え、透明になるまで加熱して攪拌し、得られるものをメタノール20gと純水200gからなる溶液に滴下し、滴下後にろ過、リンス、乾燥して、23.4g生成物a1を得た。
a1の調製工程に従って、0.0072molのa1-3を使用して0.0648molのINCと反応させ、他のパラメータ条件が変更されず、生成物a2が得られる。生成物a2を高速液体クロマトグラフで解析したところ、生成物a2におけるビスイミダゾールの合計含有量が、93.6%である。
a1の調製工程に従って、0.0648molのa1-3を使用して0.0072molのINCと反応させ、他のパラメータ条件が変更されず、生成物a3が得られる。生成物a3を高速液体クロマトグラフで解析したところ、生成物a3におけるビスイミダゾールの合計含有量が、94.9%である。
a1-3の調製工程に従ってa4-1を調製し、相違点は、1molのp-メチルベンズアルデヒドと1molのo-クロロベンズアルデヒドは、縮合、酸化反応により、1molのベンジル類化合物が得られ、このベンジル類化合物と1molの2,4-ジクロロベンズアルデヒドは、環形成反応によりモノイミダゾール化合物a4-1を生成することにある。
a1の調製工程に従って、0.048molのa4-1を使用して0.024molのINCと反応させ、他のパラメータ条件は変更されず、生成物a5が得られる。生成物a5を高速液体クロマトグラフで解析したところ、生成物a5中ビスイミダゾールの合計含有量が、95.2%である。
a1-3の調製工程に従ってa6-1を調製し、相違点は、1molp-メチルベンズアルデヒドと1molベンズアルデヒドは、縮合、酸化反応により、1molのベンジル類化合物が得られ、このベンジル類化合物と1molo-クロロベンズアルデヒドは、環形成反応により、モノイミダゾール化合物a6-1を生成することにある。
a1の調製工程に従って、0.0648molのa4-1を使用して0.0072molのINCと反応させ、他のパラメータ条件は変更されず、生成物a7が得られる。生成物a7を高速液体クロマトグラフで解析したところ、生成物a7におけるビスイミダゾールの合計含有量が、94.1%である。
a8は、Changzhou Tronly New Electronic Materials社によって製造されたBCIM(単一構造なHABI)、ここで、ヘキサアリールビスイミダゾール類光開始剤の全ての置換可能なサイトにおける赤方偏移置換基のモル比が、6.7%である。
表1-2-1に示す配合に従って、各成分を均一に混合して、感光性樹脂組成物が得られる。特に説明がない限り、表1-2-1に示す部数はいずれも質量部である。
窒素ガス雰囲気で、攪拌機、還流冷却器、温度計及び滴下ロートを備えるフラスコに、メチルセロソルブとトルエンを質量比3:2で調製した混合溶媒500gを加えて、攪拌して80℃に加熱する。メタクリル酸100g、メタクリル酸エチル200g、アクリル酸エチル100g、スチレン100gとアゾビスイソブチロニトリル0.8gを混合して得られた溶液を、ゆっくりとフラスコ中に滴下した。滴下時間が4時間であり、滴下後に引き続き2時間反応を行う。次に、フラスコにアゾビスイソブチロニトリル1.2gを溶解した混合溶媒(組成同上)100gを滴下し、滴下時間が10分間であり、滴下後に、80℃で更に3時間反応させ、更に90℃に昇温して引き続き2時間反応を行う。反応完了後、ろ過し、アルカリ可溶性ポリマーBが得られ、酸価が、196mgKOH/g、重量平均分子量が、約80000である。
3.1感光度
感光性樹脂組成物について、スピンコーターを利用して液体組成物をガラス基板上に塗工し、その後、100℃で5分間乾燥させて溶媒を除去し、厚さ10μmのコーティング膜を形成する。上記の厚さのコーティング膜を取得するために、塗工プロセスは、1回で完了しても良く、複数回で完了しても良い。コーティング膜が付けった基板を、室温に冷却し、iライン縮小投影露光装置を用いて、365nmの波長で、縦20μm×横20μmの遮蔽且つ50mJ/cm2の露光量でコーティング膜に照射した。照射後、現像液(商品名:CD-2000、60%、FUJIFILM Electronic Materials製造)を使用して、23℃で60秒間コーティング膜を現像し、その後、流水で20秒間すすいだ後、噴霧乾燥を行い、パターン画像を得た。形成された画像は光学顕微鏡によって確認される 。得られた画素パターンの幅が大きいほど感度が高くなるため、優れている。
○:35μm以上である。
◎:20μm以上35μm未満である。
●:20μm未満である。
Line/Space=10:10-150:150(単位:μm)の配線パターンを有する光マスクを利用して露光現像を行った後、分解能を測定する。分解能は、露光後に現像により形成されたレジストパターンのうち、未露光部分が除去された後のパターンの最小値であり、以下のような分級を行う。
○:分解能値が30μm以下である。
◎:分解能値が30μm-50μmであり、端点値を除く。
●:分解能値が50μm以上である。
現像後、走査型電子顕微鏡(SEM)によりフォトレジストパターンを観察し、現像性を評価した。現像性は、以下の標準で評価されました。
□:未露光部分に残存物が見られなかった。
△:未露光部分に少量の残存物が見られるが、残存量が許容範囲内にある。
×:未露光部分に明らかな残存物が見られる。
走査型電子顕微鏡(SEM)((株)日立ハイテク株式会社製、製品名“SU-1500”)を用いて、加速電圧15kV、倍率3000倍で、60度の傾斜で、レジストパターンの形状を観察し、以下の基準に従って判断した。
□:レジストパターンの形状について、アンダーカットを確認しておらず、レジストパターンの上部が欠けており、且つパターン輪廓の直線性は良好である。
△:レジストパターンの形状について、アンダーカットを確認しており、レジストパターンの上部が欠けており、且つパターン輪廓の直線性は悪かった。
親水性は、感光性樹脂層が溶解した後の沈殿量によって評価される。感光性樹脂組成物を十分に攪拌し、バーコータを使用して支持体としての厚さ25μmのポリエチレンテレフタレートフィルムの表面に均一に塗布する。乾燥機に95℃で4min乾燥し、感光性樹脂層を形成する。感光性樹脂層の層厚が約30.5μmであり、層重が約3.2gである。炭酸ナトリウム20gを2Lの水に溶解し、1.5mlのP1uronic RPG3110(BASF、Mt.Olive、NJ、この試薬はポリオキシエチレンとポリオキシプロピレン共重合体可塑剤である)を加え、現像液を調製する。上記の感光性樹脂層付きフィルムを100g現像液に入れ、樹脂層が溶解するまで試料を静置し、沈殿量は下記の等級に従って確定する。
0=沈殿量が0.005g未満である。
1=少量の細かく分散した淡黄色の物質があり、沈殿量が0.005-0.01gである。
5=中等量程度の淡黄色の物質(通常は細かい)があり、沈殿量が0.05-0.08gである。
10=固体層には大量の淡黄色の物質(通常は薄片状)があり、沈殿量が0.1g以上である。
Claims (15)
- (1)一般式(I)で表される芳香族アルデヒドと一般式(II)で表される芳香族アルデヒドは、縮合、酸化反応により、ベンジル類化合物を得り、このベンジル類化合物と一般式(III)で表される芳香族アルデヒドは、環形成反応により、モノイミダゾール化合物Mを生成するステップと、
(2)一般式(IV)で表される芳香族アルデヒドと一般式(V)で表される芳香族アルデヒドは、縮合、酸化反応により、ベンジル類化合物を得り、このベンジル類化合物と一般式(VI)で表される芳香族アルデヒドは、環形成反応により、モノイミダゾール化合物Nを生成するステップと、
(3)モノイミダゾール化合物MとNは、酸化反応により、ヘキサアリールビスイミダゾール類光開始剤を生成するステップ、によって調製してなるヘキサアリールビスイミダゾール類光開始剤。
その中で、R1-R30は、互いに独立して、水素、ハロゲン、ニトロ基、シアノ基、アミン基、ヒドロキシル基、C1-C10のアルキル基、C1-C10のアルコキシ基、又はC2-C10のアルケニル基を表し、且つ各基におけるメチレン基は、任意的に、酸素、硫黄、イミノ基で置換されても良く、
前提は、ヘキサアリールビスイミダゾール類光開始剤の全ての置換可能なサイト、即ちR1-R30における赤方偏移置換基のモル比が、6-16%である。 - 赤方偏移置換基は、塩素、臭素、ニトロ基、シアノ基、アミン基、ヒドロキシル基、C2-C10のアルケニル基、C1-C10のアルコキシ基を含み、その中で、各基におけるメチレン基は、任意的に、酸素、硫黄、イミノ基で置換されても良く、赤方偏移置換基は、塩素、臭素、ヒドロキシル基、アミン基、およびC1-C5のアルコキシ基、から選択されることが好ましい、ことを特徴とする請求項1に記載のヘキサアリールビスイミダゾール類光開始剤。
- (A)請求項1又は2に記載のヘキサアリールビスイミダゾール類光開始剤、(B)アルカリ可溶性ポリマー、(C)エチレン性不飽和二重結合を有する化合物、(D)水素供与体、(E)他の任意の助剤を含む、感光性樹脂組成物。
- 前記アルカリ可溶性ポリマーは、(メタ)アクリル酸系重合体、スチレン系重合体、エポキシ系重合体、脂肪族ポリウレタン(メタ)アクリレート重合体、芳香族ポリウレタン(メタ)アクリレート重合体、アミド系樹脂、アミドエポキシ系樹脂、アルキド系樹脂、及びフェノール系樹脂である、ことを特徴とする請求項3に記載の感光性樹脂組成物。
- 前記アルカリ可溶性ポリマーは、カルボキシル基を有するアルカリ可溶性ポリマーであり、好ましくは、カルボキシル基を有するアルカリ可溶性ポリマーは、(メタ)アクリレート、エチレン性不飽和カルボン酸、及び他の共重合可能な単量体で共重合されてなる(メタ)アクリレート系重合体である、ことを特徴とする請求項4に記載の感光性樹脂組成物。
- 前記アルカリ可溶性ポリマーの重量平均分子量は、15000-200000であり、好ましくは30000-150000であり、特に好ましくは30000-120000であり、酸価は、50-300mgKOH/g、好ましくは50-250mgKOH/gであり、更に好ましくは70-250mgKOH/gであり、特に好ましくは100-250mgKOH/gである、ことを特徴とする請求項3に記載の感光性樹脂組成物。
- 前記エチレン性不飽和二重結合を有する化合物は、α、β-不飽和カルボン酸とポリオールを反応させて得られる化合物、ビスフェノールA類(メタ)アクリレート化合物、α、β-不飽和カルボン酸とグリシジル基含有化合物と反応させて得られる化合物、分子内にウレタン結合を有する(メタ)アクリレート化合物、ノニルフェノキシポリエチレンオキシアクリレート、γ-クロロ-β-ヒドロキシプロピル-β’-(メタ)アクリロイルオキシエチル-フタレート、β-ヒドロキシエチル-β’-(メタ)アクリロイルオキシエチル-フタレート、β-ヒドロキシプロピル-β’-(メタ)アクリロイルオキシエチル-フタレート、フタル酸類化合物、アルキル(メタ)アクリレートの少なくとも一種から選択される、ことを特徴とする請求項3に記載の感光性樹脂組成物。
- 前記エチレン性不飽和二重結合を有する化合物は、ビスフェノールA類(メタ)アクリレート化合物、及び分子内にウレタン結合を有する(メタ)アクリレート化合物から選択される、ことを特徴とする請求項7に記載の感光性樹脂組成物。
- 前記水素供与体は、アミン類化合物、カルボン酸類化合物、メルカプト基を有する有機硫黄化合物又はアルコール類化合物の少なくとも一種である、ことを特徴とする請求項3に記載の感光性樹脂組成物。
- 更に、他の光開始剤及び/又は増感剤、有機溶媒、染料、顔料、光発色剤、充填剤、可塑剤、安定剤、コーティング助剤、剥離促進剤の少なくとも一種を含む、ことを特徴とする請求項3に記載の感光性樹脂組成物。
- 請求項3-10のいずれか一つに記載の感光性樹脂組成物から形成される感光性樹脂層、及び当該感光性樹脂層を支持する支持体を含む、感光性樹脂積層体。
- プリント回路板、保護パターン、導体パターン、リード線、半導体パッケージの製造における請求項3-10のいずれか一つに記載の感光性樹脂組成物又は請求項11に記載の感光性樹脂積層体の使用。
- カラーフィルタの製造における請求項3-10のいずれか一つに記載の感光性樹脂組成物又は請求項11に記載の感光性樹脂積層体の使用。
- 支持体と、支持体に請求項3-10のいずれか一つに記載の感光性樹脂組成物又は請求項11に記載の感光性樹脂積層体を使用して形成された着色パターンを含む、カラーフィルタ。
- 請求項14記載のカラーフィルタを含む、液晶ディスプレイモジュール。
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