TWI417663B - A photosensitive resin composition, a photosensitive member, a method for forming a photoresist pattern, and a method for manufacturing a printed wiring board - Google Patents
A photosensitive resin composition, a photosensitive member, a method for forming a photoresist pattern, and a method for manufacturing a printed wiring board Download PDFInfo
- Publication number
- TWI417663B TWI417663B TW099125240A TW99125240A TWI417663B TW I417663 B TWI417663 B TW I417663B TW 099125240 A TW099125240 A TW 099125240A TW 99125240 A TW99125240 A TW 99125240A TW I417663 B TWI417663 B TW I417663B
- Authority
- TW
- Taiwan
- Prior art keywords
- resin composition
- photosensitive resin
- component
- photosensitive
- phenyl
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims description 74
- 229920002120 photoresistant polymer Polymers 0.000 title claims description 54
- 238000000034 method Methods 0.000 title claims description 47
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- -1 acrylate compound Chemical class 0.000 claims description 67
- 238000002156 mixing Methods 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 21
- 238000011161 development Methods 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000000178 monomer Substances 0.000 claims description 19
- 239000004020 conductor Substances 0.000 claims description 18
- 239000011230 binding agent Substances 0.000 claims description 16
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 12
- 238000010521 absorption reaction Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229920000058 polyacrylate Polymers 0.000 claims description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 125000005907 alkyl ester group Chemical group 0.000 claims description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [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])* 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 71
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 44
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 35
- 230000035945 sensitivity Effects 0.000 description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 24
- 239000001294 propane Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 150000003219 pyrazolines Chemical class 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 10
- 229920000139 polyethylene terephthalate Polymers 0.000 description 10
- 239000005020 polyethylene terephthalate Substances 0.000 description 10
- 238000002835 absorbance Methods 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 9
- 238000007747 plating Methods 0.000 description 9
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910002601 GaN Inorganic materials 0.000 description 5
- JMASRVWKEDWRBT-UHFFFAOYSA-N Gallium nitride Chemical compound [Ga]#N JMASRVWKEDWRBT-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000005530 etching Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid group Chemical group C(C=1C(C(=O)O)=CC=CC1)(=O)O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- 150000003440 styrenes Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 206010034960 Photophobia Diseases 0.000 description 4
- 244000028419 Styrax benzoin Species 0.000 description 4
- 235000000126 Styrax benzoin Nutrition 0.000 description 4
- 235000008411 Sumatra benzointree Nutrition 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 229960002130 benzoin Drugs 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- RBVLUTAXWVILBT-UHFFFAOYSA-N ethyl prop-2-eneperoxoate Chemical compound CCOOC(=O)C=C RBVLUTAXWVILBT-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 235000019382 gum benzoic Nutrition 0.000 description 4
- 208000013469 light sensitivity Diseases 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 238000000206 photolithography Methods 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 230000001186 cumulative effect Effects 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 3
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000002518 antifoaming agent Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000003749 cleanliness Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- CDUQMGQIHYISOP-RMKNXTFCSA-N (e)-2-cyano-3-phenylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C\C1=CC=CC=C1 CDUQMGQIHYISOP-RMKNXTFCSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-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
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- GWIBWOHDQWIABB-UHFFFAOYSA-N 2,3-bis(4-dodecylphenyl)-5-[2-(4-dodecylphenyl)ethenyl]-1,3-dihydropyrazole Chemical compound C1=CC(CCCCCCCCCCCC)=CC=C1C=CC1=CC(C=2C=CC(CCCCCCCCCCCC)=CC=2)N(C=2C=CC(CCCCCCCCCCCC)=CC=2)N1 GWIBWOHDQWIABB-UHFFFAOYSA-N 0.000 description 1
- NSWNXQGJAPQOID-UHFFFAOYSA-N 2-(2-chlorophenyl)-4,5-diphenyl-1h-imidazole Chemical class ClC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 NSWNXQGJAPQOID-UHFFFAOYSA-N 0.000 description 1
- UIHRWPYOTGCOJP-UHFFFAOYSA-N 2-(2-fluorophenyl)-4,5-diphenyl-1h-imidazole Chemical class FC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 UIHRWPYOTGCOJP-UHFFFAOYSA-N 0.000 description 1
- XIOGJAPOAUEYJO-UHFFFAOYSA-N 2-(2-methoxyphenyl)-4,5-diphenyl-1h-imidazole Chemical class COC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 XIOGJAPOAUEYJO-UHFFFAOYSA-N 0.000 description 1
- GPZSKIHQGLKTSO-UHFFFAOYSA-N 2-(3,4-ditert-butylphenyl)-3-phenyl-5-(2-phenylethenyl)-1,3-dihydropyrazole Chemical compound C1=C(C(C)(C)C)C(C(C)(C)C)=CC=C1N1C(C=2C=CC=CC=2)C=C(C=CC=2C=CC=CC=2)N1 GPZSKIHQGLKTSO-UHFFFAOYSA-N 0.000 description 1
- AXGLGMITBMOBCL-UHFFFAOYSA-N 2-(3,5-ditert-butylphenyl)-3-phenyl-5-(2-phenylethenyl)-1,3-dihydropyrazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2C(C=C(C=CC=3C=CC=CC=3)N2)C=2C=CC=CC=2)=C1 AXGLGMITBMOBCL-UHFFFAOYSA-N 0.000 description 1
- OUUAUCFNNFIZOC-UHFFFAOYSA-N 2-(3-chloro-2-hydroxypropoxy)carbonylbenzoic acid Chemical compound OC(CCl)COC(=O)C1=CC=CC=C1C(O)=O OUUAUCFNNFIZOC-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
- OBNGKJXPWPAMFU-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-(4-propan-2-ylphenyl)-5-[2-(4-propan-2-ylphenyl)ethenyl]-1,3-dihydropyrazole Chemical compound C1=CC(OC)=CC=C1N1C(C=2C=CC(=CC=2)C(C)C)C=C(C=CC=2C=CC(=CC=2)C(C)C)N1 OBNGKJXPWPAMFU-UHFFFAOYSA-N 0.000 description 1
- VPPIVBRGICDJDU-UHFFFAOYSA-N 2-(4-methoxyphenyl)-3-phenyl-5-(2-phenylethenyl)-1,3-dihydropyrazole Chemical compound C1=CC(OC)=CC=C1N1C(C=2C=CC=CC=2)C=C(C=CC=2C=CC=CC=2)N1 VPPIVBRGICDJDU-UHFFFAOYSA-N 0.000 description 1
- SNFCQJAJPFWBDJ-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,5-diphenyl-1h-imidazole Chemical class C1=CC(OC)=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 SNFCQJAJPFWBDJ-UHFFFAOYSA-N 0.000 description 1
- IZDOZIGWCCYBRL-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-3-(4-methoxyphenyl)-5-[2-(4-methoxyphenyl)ethenyl]-1,3-dihydropyrazole Chemical compound C1=CC(OC)=CC=C1C=CC1=CC(C=2C=CC(OC)=CC=2)N(C=2C=CC(=CC=2)C(C)(C)C)N1 IZDOZIGWCCYBRL-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- YKYILJANBFCBQH-UHFFFAOYSA-N 2-phenoxycyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(OC=2C=CC=CC=2)=C1 YKYILJANBFCBQH-UHFFFAOYSA-N 0.000 description 1
- TWKGRZHFOJJWGP-UHFFFAOYSA-N 2-phenyl-3-(4-propan-2-ylphenyl)-5-[2-(4-propan-2-ylphenyl)ethenyl]-1,3-dihydropyrazole Chemical compound C1=CC(C(C)C)=CC=C1C=CC1=CC(C=2C=CC(=CC=2)C(C)C)N(C=2C=CC=CC=2)N1 TWKGRZHFOJJWGP-UHFFFAOYSA-N 0.000 description 1
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- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- HRVLWYIKDSTXOT-UHFFFAOYSA-N tribromo(phenyl)phosphanium Chemical compound Br[P+](Br)(Br)C1=CC=CC=C1 HRVLWYIKDSTXOT-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
- G03F7/0047—Photosensitive materials characterised by additives for obtaining a metallic or ceramic pattern, e.g. by firing
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/116—Redox or dye sensitizer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/12—Nitrogen compound containing
- Y10S430/121—Nitrogen in heterocyclic ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/146—Laser beam
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Ceramic Engineering (AREA)
- Engineering & Computer Science (AREA)
- Materials For Photolithography (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005150133 | 2005-05-23 | ||
| JP2006105416A JP4525626B2 (ja) | 2006-04-06 | 2006-04-06 | 感光性樹脂組成物、感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201100961A TW201100961A (en) | 2011-01-01 |
| TWI417663B true TWI417663B (zh) | 2013-12-01 |
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| TW099125240A TWI417663B (zh) | 2005-05-23 | 2006-05-23 | A photosensitive resin composition, a photosensitive member, a method for forming a photoresist pattern, and a method for manufacturing a printed wiring board |
| TW095118300A TW200702916A (en) | 2005-05-23 | 2006-05-23 | Photosensitive resin composition, photosensitive element, method for forming resist pattern and method for producing printed wiring board |
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| TW095118300A TW200702916A (en) | 2005-05-23 | 2006-05-23 | Photosensitive resin composition, photosensitive element, method for forming resist pattern and method for producing printed wiring board |
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| US (3) | US7993809B2 (esLanguage) |
| KR (4) | KR100934046B1 (esLanguage) |
| CN (5) | CN104111583B (esLanguage) |
| SG (1) | SG160355A1 (esLanguage) |
| TW (2) | TWI417663B (esLanguage) |
| WO (1) | WO2006126480A1 (esLanguage) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2007123062A1 (ja) * | 2006-04-18 | 2007-11-01 | Hitachi Chemical Company, Ltd. | 感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法 |
| WO2008126526A1 (ja) * | 2007-04-04 | 2008-10-23 | Asahi Kasei E-Materials Corporation | 感光性樹脂組成物および積層体 |
| JP5117233B2 (ja) * | 2008-03-21 | 2013-01-16 | 旭化成イーマテリアルズ株式会社 | 感光性樹脂組成物および積層体 |
| US8361697B2 (en) * | 2008-03-21 | 2013-01-29 | Asahi Kasei E-Materials Corporation | Photosensitive resin composition, photosensitive resin laminate, method for forming resist pattern and process for producing printed circuit board, lead frame, semiconductor package and concavoconvex board |
| JP5117234B2 (ja) * | 2008-03-21 | 2013-01-16 | 旭化成イーマテリアルズ株式会社 | 感光性樹脂組成物および積層体 |
| JP5117235B2 (ja) * | 2008-03-21 | 2013-01-16 | 旭化成イーマテリアルズ株式会社 | 感光性樹脂組成物および積層体 |
| JP5327310B2 (ja) * | 2009-02-26 | 2013-10-30 | 日立化成株式会社 | 感光性樹脂組成物、並びにこれを用いた感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法 |
| WO2011129186A1 (ja) * | 2010-04-15 | 2011-10-20 | ニチゴー・モートン株式会社 | 感光性樹脂組成物、これを用いたフォトレジストフィルム、レジストパターンの形成方法及びプリント配線板の製造方法 |
| JP5573961B2 (ja) | 2010-12-16 | 2014-08-20 | 日立化成株式会社 | 感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法 |
| CN103076717A (zh) * | 2011-10-26 | 2013-05-01 | 日立化成工业株式会社 | 感光性树脂组合物、感光性元件、抗蚀图案的形成方法及印刷配线板的制造方法 |
| JP6229256B2 (ja) * | 2011-10-31 | 2017-11-15 | 日立化成株式会社 | 感光性エレメント、レジストパターンの形成方法及びプリント配線板の製造方法 |
| WO2013084283A1 (ja) | 2011-12-05 | 2013-06-13 | 日立化成株式会社 | タッチパネル用電極の保護膜の形成方法、感光性樹脂組成物及び感光性エレメント |
| WO2013084282A1 (ja) | 2011-12-05 | 2013-06-13 | 日立化成株式会社 | 樹脂硬化膜パターンの形成方法、感光性樹脂組成物及び感光性エレメント |
| KR20130132322A (ko) * | 2012-05-25 | 2013-12-04 | 주식회사 엘지화학 | 감광성 수지 조성물, 이를 이용하여 형성된 패턴 및 이를 포함하는 디스플레이 패널 |
| WO2014196464A1 (ja) * | 2013-06-07 | 2014-12-11 | 株式会社Adeka | 着色感光性組成物及び新規化合物 |
| WO2015177947A1 (ja) * | 2014-05-23 | 2015-11-26 | 日立化成株式会社 | レジストパターンの形成方法、プリント配線板の製造方法、投影露光用感光性樹脂組成物及び感光性エレメント |
| WO2016184429A1 (zh) * | 2015-05-21 | 2016-11-24 | 常州强力先端电子材料有限公司 | 吡唑啉类增感剂及其制备方法和应用 |
| JP6911369B2 (ja) * | 2017-02-15 | 2021-07-28 | Tdk株式会社 | 積層コイル部品の製造方法 |
| WO2021075005A1 (ja) * | 2019-10-16 | 2021-04-22 | 昭和電工マテリアルズ株式会社 | 感光性樹脂フィルム、レジストパターンの形成方法、及び配線パターンの形成方法 |
| CN113929624A (zh) * | 2020-07-13 | 2022-01-14 | 常州强力电子新材料股份有限公司 | 一种吡唑啉类化合物、感光性树脂组合物及图形化方法 |
| CN120271511A (zh) * | 2025-06-09 | 2025-07-08 | 杭州福斯特电子材料有限公司 | 增感剂、感光树脂组合物、感光干膜及其制备方法 |
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| JPS62100756A (ja) * | 1985-10-29 | 1987-05-11 | Matsushita Electric Ind Co Ltd | 電子写真感光体 |
| JP2005128508A (ja) * | 2003-10-02 | 2005-05-19 | Mitsubishi Chemicals Corp | ネガ型青紫色レーザー感光性組成物、並びにそれを用いた画像形成材料、画像形成材、及び画像形成方法 |
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| JPS5575405A (en) * | 1978-11-30 | 1980-06-06 | Fuji Photo Film Co Ltd | Photopolymerizable composition |
| US4845011A (en) * | 1987-10-23 | 1989-07-04 | Hoechst Celanese Corporation | Visible light photoinitiation compositions |
| US5236812A (en) * | 1989-12-29 | 1993-08-17 | E. I. Du Pont De Nemours And Company | Solid imaging method and apparatus |
| DE4009700A1 (de) * | 1990-03-27 | 1991-10-02 | Hoechst Ag | Photopolymerisierbares gemisch und daraus hergestelltes aufzeichnungsmaterial |
| JP2931693B2 (ja) * | 1991-05-07 | 1999-08-09 | 株式会社日本化学工業所 | 光線遮蔽剤 |
| KR0150344B1 (ko) * | 1995-12-21 | 1998-10-01 | 이웅열 | 감광성 수지 조성물 |
| WO1998004407A1 (en) * | 1996-07-30 | 1998-02-05 | Hitachi Chemical Co., Ltd. | Manufacture of laminated film and printed wiring board |
| US5938761A (en) * | 1997-11-24 | 1999-08-17 | Sun Microsystems | Method and apparatus for branch target prediction |
| JP4050370B2 (ja) | 1998-01-07 | 2008-02-20 | 株式会社Ｋｒｉ | 無機質含有感光性樹脂組成物および無機パターン形成方法 |
| JP4305695B2 (ja) | 1999-05-28 | 2009-07-29 | 日立化成工業株式会社 | 感光性樹脂組成物、これを用いた感光性エレメント、レジストパターンの製造法及びプリント配線板の製造法 |
| EP1739484B1 (en) | 2000-04-19 | 2011-08-24 | AGFA Graphics NV | Photosensitive lithographic printing plate and method for making a prinitng plate. |
| JP4685259B2 (ja) * | 2000-04-19 | 2011-05-18 | コダック株式会社 | 感光性平版印刷版及び印刷版の製版方法 |
| JP3503640B2 (ja) * | 2000-09-27 | 2004-03-08 | 日立化成工業株式会社 | 感光性樹脂組成物 |
| TW562997B (en) | 2000-09-27 | 2003-11-21 | Hitachi Chemical Co Ltd | Photoresist mask pattern, and preparing method and use thereof |
| TWI296738B (esLanguage) * | 2001-03-29 | 2008-05-11 | Hitachi Chemical Co Ltd | |
| US6855480B2 (en) * | 2001-04-19 | 2005-02-15 | Shipley Company, L.L.C. | Photoresist composition |
| JP2002351070A (ja) | 2001-05-30 | 2002-12-04 | Hitachi Chem Co Ltd | 感光性樹脂組成物、これを用いた感光性エレメント、レジストパターンの製造方法及びプリント配線板の製造方法 |
| JP4043870B2 (ja) | 2002-07-10 | 2008-02-06 | 関西ペイント株式会社 | 半導体レーザー用硬化型樹脂組成物及びその組成を使用したレジストパターン形成方法 |
| US6979615B2 (en) * | 2002-09-12 | 2005-12-27 | Texas Instruments Incorporated | System and method for forming a semiconductor with an analog capacitor using fewer structure steps |
| JP4395384B2 (ja) | 2004-01-28 | 2010-01-06 | 旭化成イーマテリアルズ株式会社 | 感光性樹脂組成物及び積層体 |
| JP4223470B2 (ja) | 2004-12-03 | 2009-02-12 | 株式会社半導体エネルギー研究所 | ピッチｘの決定方法、半導体装置の作製方法 |
-
2006
- 2006-05-22 KR KR1020087028775A patent/KR100934046B1/ko active Active
- 2006-05-22 US US11/915,169 patent/US7993809B2/en active Active
- 2006-05-22 CN CN201410381347.5A patent/CN104111583B/zh active Active
- 2006-05-22 CN CN2010105396454A patent/CN102012634A/zh active Pending
- 2006-05-22 SG SG201001486-8A patent/SG160355A1/en unknown
- 2006-05-22 KR KR1020087028774A patent/KR100932581B1/ko active Active
- 2006-05-22 CN CN201410381593.0A patent/CN104133342B/zh active Active
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- 2006-05-22 WO PCT/JP2006/310134 patent/WO2006126480A1/ja not_active Ceased
- 2006-05-22 CN CNA200680017652XA patent/CN101180578A/zh active Pending
- 2006-05-22 KR KR1020077023383A patent/KR100935779B1/ko active Active
- 2006-05-22 CN CN201410381648.8A patent/CN104133343B/zh not_active Expired - Fee Related
- 2006-05-23 TW TW099125240A patent/TWI417663B/zh not_active IP Right Cessation
- 2006-05-23 TW TW095118300A patent/TW200702916A/zh unknown
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2010
- 2010-07-16 US US12/837,998 patent/US8192916B2/en active Active
- 2010-07-16 US US12/838,025 patent/US8198008B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62100756A (ja) * | 1985-10-29 | 1987-05-11 | Matsushita Electric Ind Co Ltd | 電子写真感光体 |
| JP2005128508A (ja) * | 2003-10-02 | 2005-05-19 | Mitsubishi Chemicals Corp | ネガ型青紫色レーザー感光性組成物、並びにそれを用いた画像形成材料、画像形成材、及び画像形成方法 |
Also Published As
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|---|---|
| CN104133343B (zh) | 2016-11-16 |
| US8198008B2 (en) | 2012-06-12 |
| US7993809B2 (en) | 2011-08-09 |
| KR20070110937A (ko) | 2007-11-20 |
| US20100285408A1 (en) | 2010-11-11 |
| TWI334965B (esLanguage) | 2010-12-21 |
| CN104133343A (zh) | 2014-11-05 |
| TW200702916A (en) | 2007-01-16 |
| KR100934046B1 (ko) | 2009-12-24 |
| CN101180578A (zh) | 2008-05-14 |
| CN104133342A (zh) | 2014-11-05 |
| CN104133342B (zh) | 2018-01-23 |
| KR20080108624A (ko) | 2008-12-15 |
| KR20100009547A (ko) | 2010-01-27 |
| US20100279229A1 (en) | 2010-11-04 |
| KR100935779B1 (ko) | 2010-01-06 |
| CN104111583A (zh) | 2014-10-22 |
| CN104111583B (zh) | 2019-01-01 |
| WO2006126480A1 (ja) | 2006-11-30 |
| TW201100961A (en) | 2011-01-01 |
| KR100932581B1 (ko) | 2009-12-17 |
| SG160355A1 (en) | 2010-04-29 |
| CN102012634A (zh) | 2011-04-13 |
| US20090029289A1 (en) | 2009-01-29 |
| KR20080108623A (ko) | 2008-12-15 |
| KR100953245B1 (ko) | 2010-04-16 |
| US8192916B2 (en) | 2012-06-05 |
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