JP5623416B2 - 光開始剤混合物 - Google Patents
光開始剤混合物 Download PDFInfo
- Publication number
- JP5623416B2 JP5623416B2 JP2011535068A JP2011535068A JP5623416B2 JP 5623416 B2 JP5623416 B2 JP 5623416B2 JP 2011535068 A JP2011535068 A JP 2011535068A JP 2011535068 A JP2011535068 A JP 2011535068A JP 5623416 B2 JP5623416 B2 JP 5623416B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- substituted
- optionally
- halogen
- 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.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims description 247
- -1 C 1 -C 20 - alkyl Chemical group 0.000 claims description 331
- 150000001875 compounds Chemical class 0.000 claims description 198
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 180
- 229910052736 halogen Inorganic materials 0.000 claims description 105
- 150000002367 halogens Chemical class 0.000 claims description 103
- 239000000976 ink Substances 0.000 claims description 95
- 239000000049 pigment Substances 0.000 claims description 88
- 238000007639 printing Methods 0.000 claims description 77
- 239000001257 hydrogen Substances 0.000 claims description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims description 70
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 62
- 229910052760 oxygen Inorganic materials 0.000 claims description 54
- 238000000576 coating method Methods 0.000 claims description 47
- 238000000034 method Methods 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000001624 naphthyl group Chemical group 0.000 claims description 41
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 40
- 239000000758 substrate Substances 0.000 claims description 39
- 238000004519 manufacturing process Methods 0.000 claims description 38
- 239000000463 material Substances 0.000 claims description 37
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 37
- 229910052717 sulfur Inorganic materials 0.000 claims description 34
- 229920005989 resin Polymers 0.000 claims description 32
- 239000011347 resin Substances 0.000 claims description 32
- 239000011248 coating agent Substances 0.000 claims description 31
- 239000012965 benzophenone Substances 0.000 claims description 30
- 239000000654 additive Substances 0.000 claims description 28
- 229910052740 iodine Inorganic materials 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 239000002270 dispersing agent Substances 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 239000000843 powder Substances 0.000 claims description 21
- YBFHILNBYXCJKD-UHFFFAOYSA-N 1-(6-methylpyridin-3-yl)-2-(4-methylsulfonylphenyl)ethanone Chemical compound C1=NC(C)=CC=C1C(=O)CC1=CC=C(S(C)(=O)=O)C=C1 YBFHILNBYXCJKD-UHFFFAOYSA-N 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 18
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 17
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 16
- 239000000853 adhesive Substances 0.000 claims description 16
- 230000001070 adhesive effect Effects 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 16
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 229920000647 polyepoxide Polymers 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 15
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 13
- 229920002120 photoresistant polymer Polymers 0.000 claims description 13
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 12
- 230000003287 optical effect Effects 0.000 claims description 12
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 11
- 150000008065 acid anhydrides Chemical class 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 11
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 239000003973 paint Substances 0.000 claims description 10
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 9
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
- 150000007519 polyprotic acids Polymers 0.000 claims description 9
- 229910000679 solder Inorganic materials 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 8
- 238000013500 data storage Methods 0.000 claims description 8
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 8
- 238000007650 screen-printing Methods 0.000 claims description 8
- 230000000996 additive effect Effects 0.000 claims description 7
- 125000004957 naphthylene group Chemical group 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000003822 epoxy resin Substances 0.000 claims description 6
- 238000003384 imaging method Methods 0.000 claims description 6
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 5
- 230000005670 electromagnetic radiation Effects 0.000 claims description 5
- 238000009713 electroplating Methods 0.000 claims description 5
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 claims description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000006850 spacer group Chemical group 0.000 claims description 5
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 238000007747 plating Methods 0.000 claims description 4
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 claims description 4
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 3
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 239000008247 solid mixture Substances 0.000 claims description 3
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- VWBYXJRDIQCSLW-UHFFFAOYSA-N O=[P](c1ccccc1)c1ccccc1 Chemical group O=[P](c1ccccc1)c1ccccc1 VWBYXJRDIQCSLW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims 2
- 238000010276 construction Methods 0.000 claims 2
- 239000011152 fibreglass Substances 0.000 claims 2
- 238000004377 microelectronic Methods 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- KOMDZQSPRDYARS-UHFFFAOYSA-N cyclopenta-1,3-diene titanium Chemical compound [Ti].C1C=CC=C1.C1C=CC=C1 KOMDZQSPRDYARS-UHFFFAOYSA-N 0.000 claims 1
- 150000002763 monocarboxylic acids Chemical class 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 165
- 229920000642 polymer Polymers 0.000 description 61
- 229920001577 copolymer Polymers 0.000 description 60
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 49
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 45
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 44
- 150000002431 hydrogen Chemical class 0.000 description 42
- 239000010410 layer Substances 0.000 description 42
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 35
- 229920005862 polyol Polymers 0.000 description 35
- 239000000178 monomer Substances 0.000 description 31
- 238000002360 preparation method Methods 0.000 description 31
- 239000002253 acid Substances 0.000 description 30
- 239000011230 binding agent Substances 0.000 description 28
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 27
- 150000003077 polyols Chemical class 0.000 description 25
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 24
- 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 23
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- 239000010408 film Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- 230000005855 radiation Effects 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 19
- 239000000975 dye Substances 0.000 description 19
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 19
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 17
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 17
- 239000006185 dispersion Substances 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 16
- 239000003960 organic solvent Substances 0.000 description 16
- 229920000728 polyester Polymers 0.000 description 16
- 229920001223 polyethylene glycol Polymers 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- 229940059574 pentaerithrityl Drugs 0.000 description 15
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 15
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000004094 surface-active agent Substances 0.000 description 14
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 13
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- 239000002202 Polyethylene glycol Substances 0.000 description 13
- 150000001735 carboxylic acids Chemical class 0.000 description 13
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 13
- 125000004430 oxygen atom Chemical group O* 0.000 description 13
- 239000000600 sorbitol Substances 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 12
- 238000001723 curing Methods 0.000 description 12
- 125000003700 epoxy group Chemical group 0.000 description 12
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 239000004814 polyurethane Substances 0.000 description 12
- 229920002635 polyurethane Polymers 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 11
- 239000004642 Polyimide Substances 0.000 description 11
- 239000003086 colorant Substances 0.000 description 11
- 125000004386 diacrylate group Chemical group 0.000 description 11
- 239000011521 glass Substances 0.000 description 11
- 229920001721 polyimide Polymers 0.000 description 11
- 239000011342 resin composition Substances 0.000 description 11
- 229920002554 vinyl polymer Polymers 0.000 description 11
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 239000003999 initiator Substances 0.000 description 10
- 239000011976 maleic acid Substances 0.000 description 10
- 0 C*1C2=CCCCC12 Chemical compound C*1C2=CCCCC12 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 9
- 235000011187 glycerol Nutrition 0.000 description 9
- 239000004973 liquid crystal related substance Substances 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 9
- 229920003986 novolac Polymers 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 8
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 238000007645 offset printing Methods 0.000 description 8
- 229920000570 polyether Polymers 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229920001187 thermosetting polymer Polymers 0.000 description 8
- 125000001544 thienyl group Chemical group 0.000 description 8
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 7
- OMJKVIFSWSQTGQ-UHFFFAOYSA-N 6,7-bis(aziridin-1-yl)quinazoline-5,8-dione Chemical compound C1CN1C=1C(=O)C2=NC=NC=C2C(=O)C=1N1CC1 OMJKVIFSWSQTGQ-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
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- 125000002768 hydroxyalkyl group Chemical group 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 6
- 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 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 6
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- GKRVGTLVYRYCFR-UHFFFAOYSA-N butane-1,4-diol;2-methylidenebutanedioic acid Chemical compound OCCCCO.OC(=O)CC(=C)C(O)=O.OC(=O)CC(=C)C(O)=O GKRVGTLVYRYCFR-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 238000010894 electron beam technology Methods 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000003365 glass fiber Substances 0.000 description 6
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- 125000001312 palmitoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
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- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 1
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- GVVKBARIYRBZHC-UHFFFAOYSA-N prop-2-enyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCC=C GVVKBARIYRBZHC-UHFFFAOYSA-N 0.000 description 1
- CYFIHPJVHCCGTF-UHFFFAOYSA-N prop-2-enyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OCC=C CYFIHPJVHCCGTF-UHFFFAOYSA-N 0.000 description 1
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- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
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- UWGCNDBLFSEBDW-UHFFFAOYSA-M sodium;4-[[4-(diethylamino)phenyl]-(4-diethylazaniumylidenecyclohexa-2,5-dien-1-ylidene)methyl]naphthalene-2,7-disulfonate Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C2=CC=C(C=C2C=C(C=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 UWGCNDBLFSEBDW-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- 125000004079 stearyl 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])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
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- PMJMHCXAGMRGBZ-UHFFFAOYSA-N subphthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(=N3)N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C3=N1 PMJMHCXAGMRGBZ-UHFFFAOYSA-N 0.000 description 1
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- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
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- 125000005207 tetraalkylammonium group Chemical group 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical compound C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- JADVWWSKYZXRGX-UHFFFAOYSA-M thioflavine T Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C1=[N+](C)C2=CC=C(C)C=C2S1 JADVWWSKYZXRGX-UHFFFAOYSA-M 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- AYNNSCRYTDRFCP-UHFFFAOYSA-N triazene Chemical compound NN=N AYNNSCRYTDRFCP-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- XOALFFJGWSCQEO-UHFFFAOYSA-N tridecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C=C XOALFFJGWSCQEO-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical class C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- 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
- G03F7/031—Organic compounds not covered by group G03F7/029
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Dental Preparations (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Materials For Photolithography (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08168145.4 | 2008-11-03 | ||
| EP08168145 | 2008-11-03 | ||
| PCT/EP2009/063963 WO2010060702A1 (en) | 2008-11-03 | 2009-10-23 | Photoinitiator mixtures |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012507571A JP2012507571A (ja) | 2012-03-29 |
| JP2012507571A5 JP2012507571A5 (enExample) | 2012-12-06 |
| JP5623416B2 true JP5623416B2 (ja) | 2014-11-12 |
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| JP2011535068A Expired - Fee Related JP5623416B2 (ja) | 2008-11-03 | 2009-10-23 | 光開始剤混合物 |
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| US (1) | US8507726B2 (enExample) |
| EP (1) | EP2342237B1 (enExample) |
| JP (1) | JP5623416B2 (enExample) |
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| CN (1) | CN102203136B (enExample) |
| TW (1) | TWI453184B (enExample) |
| WO (1) | WO2010060702A1 (enExample) |
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| US9051397B2 (en) | 2010-10-05 | 2015-06-09 | Basf Se | Oxime ester |
| JP5677036B2 (ja) | 2010-11-08 | 2015-02-25 | キヤノン株式会社 | 有機発光素子 |
| JP5821401B2 (ja) * | 2011-08-19 | 2015-11-24 | 大日本印刷株式会社 | 光インプリント用感光性樹脂組成物、硬化物、レジスト基板及び半導体装置の製造方法 |
| US9365515B2 (en) | 2011-12-07 | 2016-06-14 | Basf Se | Oxime ester photoinitiators |
| US8878169B2 (en) * | 2012-02-07 | 2014-11-04 | Polyera Corporation | Photocurable polymeric materials and related electronic devices |
| RU2613408C2 (ru) | 2012-03-22 | 2017-03-16 | Зм Инновейтив Пропертиз Компани | Композиция твердого покрытия на основе полиметилметакрилата и изделие с покрытием |
| US9050820B2 (en) | 2012-12-29 | 2015-06-09 | Atasheh Soleimani-Gorgani | Three-dimensional ink-jet printing by home and office ink-jet printer |
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| CN110076867B (zh) * | 2019-04-28 | 2020-12-15 | 福建农林大学 | 基于环氧树脂的木塑复合材料辐射固化方法 |
| KR102275249B1 (ko) * | 2019-11-25 | 2021-07-12 | 주식회사 케이씨씨 | 광경화성 수지 조성물 |
| CN113126369A (zh) * | 2021-04-09 | 2021-07-16 | 西京学院 | 一种液晶复合薄膜及其制备方法和液晶书写板 |
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| WO2025054034A2 (en) * | 2023-09-05 | 2025-03-13 | Eastman Chemical Company | Energy curable ink compositions and methods thereof |
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| KR20250088054A (ko) * | 2023-12-08 | 2025-06-17 | 주식회사 동진쎄미켐 | 광경화성 조성물, 점착제 및 디스플레이 장치 |
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| WO2008138733A1 (en) * | 2007-05-11 | 2008-11-20 | Basf Se | Oxime ester photoinitiators |
| EP2402315A1 (en) * | 2007-05-11 | 2012-01-04 | Basf Se | Oxime ester photoinitiators |
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| WO2009147031A2 (en) | 2008-06-06 | 2009-12-10 | Basf Se | Oxime ester photoinitiators |
| EP2285836B1 (en) * | 2008-06-06 | 2012-01-18 | Basf Se | Photoinitiator mixtures |
| WO2010003811A1 (en) * | 2008-07-11 | 2010-01-14 | Basf Se | Amphiphilic proteins as morphology modifiers |
-
2009
- 2009-10-23 US US13/127,068 patent/US8507726B2/en not_active Expired - Fee Related
- 2009-10-23 CN CN2009801436477A patent/CN102203136B/zh not_active Expired - Fee Related
- 2009-10-23 EP EP09737002.7A patent/EP2342237B1/en not_active Not-in-force
- 2009-10-23 KR KR1020117012660A patent/KR101648996B1/ko not_active Expired - Fee Related
- 2009-10-23 JP JP2011535068A patent/JP5623416B2/ja not_active Expired - Fee Related
- 2009-10-23 WO PCT/EP2009/063963 patent/WO2010060702A1/en not_active Ceased
- 2009-11-02 TW TW098137142A patent/TWI453184B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012507571A (ja) | 2012-03-29 |
| CN102203136B (zh) | 2013-11-13 |
| US8507726B2 (en) | 2013-08-13 |
| KR20110091742A (ko) | 2011-08-12 |
| TWI453184B (zh) | 2014-09-21 |
| KR101648996B1 (ko) | 2016-08-17 |
| CN102203136A (zh) | 2011-09-28 |
| TW201033161A (en) | 2010-09-16 |
| EP2342237A1 (en) | 2011-07-13 |
| EP2342237B1 (en) | 2014-04-23 |
| WO2010060702A1 (en) | 2010-06-03 |
| US20110218266A1 (en) | 2011-09-08 |
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