TWI423960B - Novel epoxy compounds, alkaline developing resin compositions and alkaline developing photosensitive resin compositions - Google Patents
Novel epoxy compounds, alkaline developing resin compositions and alkaline developing photosensitive resin compositions Download PDFInfo
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- TWI423960B TWI423960B TW097116672A TW97116672A TWI423960B TW I423960 B TWI423960 B TW I423960B TW 097116672 A TW097116672 A TW 097116672A TW 97116672 A TW97116672 A TW 97116672A TW I423960 B TWI423960 B TW I423960B
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- Prior art keywords
- compound
- resin composition
- group
- alkali
- epoxy
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 299
- 239000004593 Epoxy Substances 0.000 title claims abstract description 118
- 239000011342 resin composition Substances 0.000 title claims description 159
- 238000011161 development Methods 0.000 title description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 11
- 230000003287 optical effect Effects 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims description 45
- 150000008065 acid anhydrides Chemical class 0.000 claims description 39
- 239000002253 acid Substances 0.000 claims description 35
- 150000007519 polyprotic acids Polymers 0.000 claims description 22
- 239000003822 epoxy resin Substances 0.000 claims description 20
- 229920000647 polyepoxide Polymers 0.000 claims description 20
- 239000007795 chemical reaction product Substances 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 239000003999 initiator Substances 0.000 claims description 12
- 239000000463 material Substances 0.000 claims description 10
- 238000004040 coloring Methods 0.000 claims description 8
- 238000005886 esterification reaction Methods 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- 239000004848 polyfunctional curative Substances 0.000 claims description 2
- -1 bisphenol compound Chemical class 0.000 description 118
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000002904 solvent Substances 0.000 description 37
- 230000000052 comparative effect Effects 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 30
- 239000000243 solution Substances 0.000 description 29
- 238000004519 manufacturing process Methods 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000003756 stirring Methods 0.000 description 23
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 22
- 229930185605 Bisphenol Natural products 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 238000001816 cooling Methods 0.000 description 19
- 125000003700 epoxy group Chemical group 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- 239000002585 base Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000011572 manganese Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 10
- 239000000975 dye Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 239000003513 alkali Substances 0.000 description 9
- 230000035945 sensitivity Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000000123 paper Substances 0.000 description 7
- 239000000049 pigment Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical group 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 6
- 229920003986 novolac Polymers 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229920000768 polyamine Polymers 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- CIRFCTNAERFXRM-UHFFFAOYSA-N 4-(5-butylnonan-5-yl)phenol Chemical compound C(CCC)C(C=1C=CC(=CC1)O)(CCCC)CCCC CIRFCTNAERFXRM-UHFFFAOYSA-N 0.000 description 5
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000000853 adhesive Substances 0.000 description 5
- 230000001070 adhesive effect Effects 0.000 description 5
- 239000006229 carbon black Substances 0.000 description 5
- 239000013067 intermediate product Substances 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000001993 wax 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
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 229910000420 cerium oxide Inorganic materials 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 235000007586 terpenes Nutrition 0.000 description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-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
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000005605 benzo group Chemical group 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
- 239000004927 clay Substances 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- SOOZEQGBHHIHEF-UHFFFAOYSA-N methyltetrahydrophthalic anhydride Chemical compound C1C=CCC2C(=O)OC(=O)C21C SOOZEQGBHHIHEF-UHFFFAOYSA-N 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 3
- 235000019799 monosodium phosphate Nutrition 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229920000620 organic polymer Polymers 0.000 description 3
- 238000007639 printing Methods 0.000 description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- 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 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- NPKKFQUHBHQTSH-UHFFFAOYSA-N 2-(decoxymethyl)oxirane Chemical compound CCCCCCCCCCOCC1CO1 NPKKFQUHBHQTSH-UHFFFAOYSA-N 0.000 description 2
- YOVCZPMFRPKCTN-UHFFFAOYSA-N 2-[[4-[9-[4-(oxiran-2-ylmethoxy)phenyl]-10H-anthracen-9-yl]phenoxy]methyl]oxirane Chemical compound C(OC1=CC=C(C=C1)C1(C2=CC=C(OCC3CO3)C=C2)C2=CC=CC=C2CC2=C1C=CC=C2)C1CO1 YOVCZPMFRPKCTN-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
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- 235000011007 phosphoric acid Nutrition 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 239000001007 phthalocyanine dye Substances 0.000 description 1
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- 238000005498 polishing Methods 0.000 description 1
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- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
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- 238000011160 research Methods 0.000 description 1
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- 229960001755 resorcinol Drugs 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
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- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
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- ADXGNEYLLLSOAR-UHFFFAOYSA-N tasosartan Chemical compound C12=NC(C)=NC(C)=C2CCC(=O)N1CC(C=C1)=CC=C1C1=CC=CC=C1C=1N=NNN=1 ADXGNEYLLLSOAR-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000001017 thiazole dye Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- NJRXVEJTAYWCQJ-UHFFFAOYSA-N thiomalic acid Chemical compound OC(=O)CC(S)C(O)=O NJRXVEJTAYWCQJ-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
- 229940103494 thiosalicylic acid Drugs 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- UMMDBKGUDMBUSR-UHFFFAOYSA-M tris-decyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(CCCCCCCCCC)CCCCCCCCCC UMMDBKGUDMBUSR-UHFFFAOYSA-M 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
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Description
本發明係關於一種具有苯并或萘并環烷烴骨架之新穎環氧化合物、對該環氧化合物賦予乙烯性不飽和鍵所形成之特定化合物、含有由該化合物與多元酸酐之酯化反應所獲得之化合物的鹼性顯影性樹脂組合物、以及於該鹼性顯影性樹脂組合物中含有光聚合起始劑而成之鹼性顯影性感光性樹脂組合物。
鹼性顯影性感光性樹脂組合物包含鹼性顯影性樹脂組合物及光聚合起始劑,且該鹼性顯影性樹脂組合物含有具有乙烯性不飽和鍵之化合物。該鹼性顯影性感光性樹脂組合物可藉由照射紫外線或電子束而聚合硬化,因此將其應用於光硬化性油墨、感光性印刷板、印刷電路板、各種光阻劑等中。近來,伴隨電子設備之輕薄短小化及高功能化之發展,期待一種可高精度地形成微細圖案之鹼性顯影性感光性樹脂組合物。
關於鹼性顯影性樹脂組合物及鹼性顯影性感光性樹脂組合物,下述專利文獻1中提出一種含有具有乙烯性不飽和鍵之預聚物之感光性樹脂組合物。又,下述專利文獻2中提出一種含有具有不飽和基之聚羧酸樹脂之感光性樹脂組合物。然而,該等公知之鹼性顯影性感光性樹脂組合物於靈敏度、析像度或密著性方面不充分,難以獲得適當之圖案形狀或微細圖案。故而,期待一種靈敏度及密著性優
異,可高精度地形成微細圖案的鹼性顯影性感光性樹脂組合物。
又,下述非專利文獻1中揭示有一種具有苯并環烷烴骨架之雙酚化合物,但並未揭示亦未啟示有將該雙酚化合物衍生為環氧化合物之例。
專利文獻1:日本專利特開2000-235261號公報
專利文獻2:日本專利特開2000-355621號公報
非專利文獻1:Macromolecules,3,536(1970)
本發明所欲解決之問題點在於:如上所述,迄今為止並未出現一種靈敏度及密著性優異,可獲得適當之圖案形狀或微細圖案的鹼性顯影性樹脂組合物及鹼性顯影性感光性樹脂組合物。
因此,本發明之目的在於提供:一種可用作靈敏度及密著性等優異,能高精度地形成微細圖案之鹼性顯影性樹脂組合物及鹼性顯影性感光性樹脂組合物之原料的新穎化合物;以及使用有該化合物之鹼性顯影性樹脂組合物及鹼性顯影性感光性樹脂組合物。
本發明者反覆進行努力研究,結果發現具有苯并或萘并環烷烴骨架之新穎環氧化合物可達成上述目的。
本發明係基於上述認識而完成者,其提供一種以下述通式(I)所表示之環氧化合物(A):
(式中,X、Y及Z係分別獨立表示可經鹵素原子取代之碳原子數為1~10之烷基、可經鹵素原子取代之碳原子數為6~20之芳基、可經鹵素原子取代之碳原子數為7~20之芳烷基、可經鹵素原子取代之碳原子數為2~20之雜環基或鹵素原子,該烷基、芳基及芳烷基中之亞甲基可由不飽和鍵、-O-或-S-所中斷;對於X,X彼此可形成環,且其等之環可為芳香環;k表示0~4之數,p表示0~8之數,r表示0~4之數,n表示0~10之數,x表示0~4之數,y表示0~4之數,x與y之數之合計為2~4;n不為0時存在之光學異構物可為任意異構物)。
又,本發明提供一種環氧加成化合物(W),其具有於上述環氧化合物(A)上加成不飽和一元酸(B)之結構。
又,本發明提供一種環氧樹脂組合物,其包含上述環氧化合物(A)及硬化劑。
又,本發明提供一種鹼性顯影性樹脂組合物,其特徵在於:含有光聚合性不飽和化合物(X),該化合物具有由上述環氧加成化合物(W)與多元酸酐(C)之酯化反應所獲得的反應產物之結構。
又,本發明提供一種鹼性顯影性樹脂組合物,其特徵在於:含有光聚合性不飽和化合物(Y),該化合物具有於上
述光聚合性不飽和化合物(X)上進一步加成環氧化合物(D)而獲得的反應產物之結構。
又,本發明提供一種鹼性顯影性樹脂組合物,其特徵在於:含有光聚合性不飽和化合物(Z),該化合物具有使上述光聚合性不飽和化合物(Y)進一步與多元酸酐(E)進行酯化反應而獲得的反應產物之結構。
又,本發明提供一種鹼性顯影性感光性樹脂組合物,其特徵在於:使上述鹼性顯影性樹脂組合物中含有光聚合起始劑(F)。
又,本發明提供一種著色鹼性顯影性感光性樹脂組合物,其特徵在於:使上述鹼性顯影性感光性樹脂組合物中進一步含有色料(G)。
以下,基於較佳實施形態,對本發明之環氧化合物(A)、環氧加成化合物(W)、環氧樹脂組合物、鹼性顯影性樹脂組合物、鹼性顯影性感光性樹脂組合物及著色鹼性顯影性感光性樹脂組合物加以詳細說明。
於本發明之環氧化合物(A)中,上述通式(I)中,作為X、Y及Z所表示之可經鹵素原子取代之碳原子數為1~10之烷基,例如可列舉甲基、乙基、丙基、異丙基、丁基、第二丁基、第三丁基、異丁基、戊基、異戊基、第三戊基、己基、庚基、異庚基、第三庚基、正辛基、異辛基、第三辛基、2-乙基己基、正壬基、正癸基、三氟甲基、二氟甲基、單氟甲基、五氟乙基、四氟乙基、三氟乙基、二氟乙
基、七氟丙基、六氟丙基、五氟丙基、四氟丙基、三氟丙基、全氟丁基、甲氧基、甲氧基乙氧基、甲氧基乙氧基乙氧基、甲硫基、乙氧基、乙烯氧基、丙氧基、異丙氧基、丁氧基、異丁氧基、第三丁氧基、第三丁氧基羰基甲氧基、戊氧基、異戊氧基、第三戊氧基、新戊氧基、己氧基、環己氧基、異己氧基、庚氧基、辛氧基、2-乙基己氧基、壬氧基、癸氧基、環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基等直鏈、支鏈及環狀之烷基;作為可經鹵素原子取代之碳原子數為6~20之芳基,例如可列舉苯基、1-萘基、2-萘基、1-蒽基、1-菲基、鄰甲苯基、間甲苯基、對甲苯基、3-茀基、9-茀基、1-四氫萘基、2-四氫萘基、1-二氫苊基、1-二氫茚基、2-二氫茚基、4-乙烯基苯基、3-異丙基苯基、4-異丙基苯基、4-丁基苯基、4-異丁基苯基、4-第三丁基苯基、4-己基苯基、4-環己基苯基、4-辛基苯基、4-(2-乙基己基)苯基、2,3-二甲基苯基、2,4-二甲基苯基、2,5-二甲基苯基、2,6-二甲基苯基、3,4-二甲基苯基、3,5-二甲基苯基、2,4-二-第三丁基苯基、2,5-二-第三丁基苯基、2,6-二-第三丁基苯基、2,4-二-第三戊基苯基、2,5-二-第三戊基苯基、環己基苯基、聯苯基、2,4,5-三甲基苯基、4-氯苯基、3,4-二氯苯基、4-三氯苯基、4-三氟苯基、全氟苯基、苯氧基、2-甲基苯氧基、3-甲基苯氧基、4-甲基苯氧基、2,3-二甲基苯氧基、2,4-二甲基苯氧基、2,5-二甲基苯氧基、2,6-二甲基苯氧基、3,4-二甲基苯氧基、3,5-二甲基苯氧基、
2,3,4-三甲基苯氧基、2,3,5-三甲基苯氧基、2,3,6-三甲基苯氧基、2,4,5-三甲基苯氧基、2,4,6-三甲基苯氧基、3,4,5-三甲基苯氧基、2,3,4,5-四甲基苯氧基、2,3,4,6-四甲基苯氧基、2,3,5,6-四甲基苯氧基、五甲基苯氧基、乙基苯氧基、正丙基苯氧基、異丙基苯氧基、正丁基苯氧基、第二丁基苯氧基、第三丁基苯氧基、正己基苯氧基、正辛基苯氧基、正癸基苯氧基、正十四烷基苯氧基、1-萘氧基、2-萘氧基、1-蒽氧基、1-菲氧基、鄰甲苯氧基、間甲苯氧基、對甲苯氧基、9-茀氧基、1-四氫萘氧基、2-四氫萘氧基、1-二氫苊氧基、1-二氫茚氧基、2-二氫茚氧基等;作為可經鹵素原子取代之碳原子數為7~20之芳烷基,例如可列舉苄基、苯乙基、2-苯基丙基、二苯基甲基、三苯基甲基、苯乙烯基、苯烯丙基、4-氯苯基甲基、苄氧基、1-萘基甲氧基、2-萘基甲氧基、1-蒽基甲氧基等;作為可經鹵素原子取代之碳原子數為2~20之雜環基,例如可列舉吡咯基、吡啶基、嘧啶基、噠嗪基、哌嗪基、哌啶基、吡喃基、吡唑基、三嗪基、吡咯啶基、喹啉基、異喹啉基、咪唑基、苯并咪唑基、***基、呋喃基(furyl)、呋喃基(furanyl)、苯并呋喃基、噻吩基(thienyl)、噻吩基(thiophenyl)、苯并噻吩基、噻二唑基、噻唑基、苯并噻唑基、唑基、苯并唑基、異噻唑基、異唑基、吲哚基、尿啶基(uroridyl)、嗎啉基、硫代嗎啉基、2-吡咯啶酮-1-基、2-哌啶酮-1-基、2,4-二氧基咪唑啶-3-基、2,4-二氧基唑啶-3-基等;作為鹵素原子,可列舉氟、氯、溴、
碘;作為可由X彼此所形成之環結構,例如可列舉環戊烷環、環己烷環、環戊烯環、苯環、哌啶環、嗎啉環、內酯環、內醯胺環等5~7員環,以及萘環、蒽環、茀環、二氫苊環、二氫茚環、四氫萘環等稠環。
上述X、Y及Z所表示之烷基、芳基、芳烷基中之亞甲基可由不飽和鍵、-O-或-S-所中斷,鹵基之取代位置及-O-或-S-之中斷位置為任意位置,-O-或-S-包含與各環直接鍵結者。
當本發明之環氧化合物(A)中之n不為0時,有時存在光學異構物,該光學異構物可為任意異構物,以下之本文中所示之化合物並不限定於特定之光學異構物。
作為本發明之環氧化合物(A),例如可列舉下述[化2]~[化9]所示之化合物,但並非限定於該等化合物。再者,下述化學式中,n表示0~10之數。
作為本發明之環氧化合物(A),較好的是下述化合物,即,x為2或3,y為0,X為碳原子數為1~10之烷基、碳原子
數為6~20之芳基或X彼此所形成之環為芳香環之基,Y及Z為碳原子數為1~10之烷基或碳原子數為6~20之芳基,k、p及r分別獨立為0~2的化合物,其原因在於,此種化合物容易獲得原料、生產性佳、疏水性強,因此作為環氧樹脂之特性良好。
本發明之環氧化合物(A)之製造方法並不受特別限定,例如,可藉由下述方法容易地製造本發明之環氧化合物(A):使苯并或萘并環烷酮衍生物(1)與酚衍生物於酸性觸媒存在下反應,藉此獲得作為中間產物之雙酚化合物(2),使該雙酚化合物(2)與表氯醇於鹼、路易斯酸或相間轉移觸媒之存在下反應。以下揭示其製造流程。再者,下式中之X、Y、Z、k、p、r、x、y及n與上述通式(I)相同。
製造本發明之環氧化合物(A)時,有時係獲得光學異構物之混合物,但於本發明之使用範圍內可並無問題地加以
使用。
上述製造方法中,作為用以製造作為中間產物之上述雙酚化合物(2)之條件,可採用先前公知之條件,例如,藉由於酸性觸媒之存在下,於20~200℃之溫度下反應1~40小時而獲得。
作為上述酸性觸媒,例如可列舉:甲磺酸、苯磺酸、間二甲苯磺酸、對甲苯磺酸、羥甲基磺酸、2-羥乙基磺酸、羥丙基磺酸、三氟甲磺酸、磺基水楊酸、磺基鄰苯二甲酸等磺酸類;硫酸、無水硫酸、發煙硫酸、氯硫酸、氟硫酸、鹽酸、氯化氫氣體、草酸、甲酸、磷酸、三氯乙酸、三氟乙酸,矽鎢酸、磷鎢酸等雜多酸,強酸性之離子交換樹脂、活性白土、三氟化硼、無水氯化鋁、氯化鋅等。該酸性觸媒相對於上述苯并環烷酮衍生物(1)100質量份,較好的是使用0.1~50質量份,更好的是使用10~30質量份。
進而,為促進反應亦可使用硫醇觸媒,作為該硫醇觸媒,例如可列舉:甲硫醇、乙硫醇、丙硫醇、丁硫醇、辛硫醇、十二硫醇、1,6-己二硫醇等烷基硫醇類;硫酚、甲硫酚等芳香族硫醇類;巰基乙酸(硫醇乙酸)、3-巰基丙酸、巰基十一酸、硫苯甲酸等巰基有機酸類;2-巰基苯并噻唑等雜環族硫醇類等。
又,上述反應中可使用先前公知之溶劑,作為該溶劑,例如可列舉:甲苯、二甲苯、異丙苯等芳香族烴系溶劑;松節油、D-檸檬烯(D-Limonene,右旋檸檬烯)、蒎烯等萜烯系烴油;礦油精、Swasol#310(Cosmo Matsuyama Oil股
份有限公司)、Solvesso#100(Exxon Chemical股份有限公司)等鏈烷烴系溶劑;甲醇、乙醇等醇系溶劑;乙酸乙酯等酯溶劑;二氯乙烷、四氯化碳、氯仿、三氯乙烯、二氯甲烷、氯苯等鹵素系溶劑;四氫呋喃、二烷等環狀醚系溶劑;醚類、溶纖劑系溶劑、酮系溶劑、苯胺、三乙胺、吡啶、二烷、乙酸、乙腈、二硫化碳等。
又,用以由作為中間產物之上述雙酚化合物(2)與表氯醇製造本發明之環氧化合物(A)的條件,可採用先前公知之條件,例如,使作為中間產物之上述雙酚化合物(2)與表氯醇於鹼、路易斯酸或相間轉移觸媒之存在下,於20~100℃,尤其好的是於30~80℃之範圍內反應,若小於20℃,則反應變慢而需要進行長時間之反應,若超過100℃,則會產生較多副反應,故欠佳。
作為上述反應中所使用之鹼,例如可列舉氫氧化鈉、氫氧化鉀、氫氧化鈣等;作為路易斯酸,除如上所例示之酸性觸媒以外,還可列舉四氯化錫、三氟化硼、四氯化鈦、活性白土、氯化鋁、氯化鎂、高錳酸鉀、鉻酸鉀等;作為相間轉移觸媒,例如可列舉四甲基氯化銨、四丁基溴化銨、甲基三辛基氯化銨、甲基十三烷基氯化銨、苄基三乙基氯化銨、N,N-二甲基吡咯烷鎓氯化物、N-乙基-N-甲基吡咯烷鎓碘化物、N-丁基-N-甲基吡咯烷鎓溴化物、N-苄基-N-甲基吡咯烷鎓氯化物、N-乙基-N-甲基吡咯烷鎓溴化物、N-丁基-N-甲基嗎啉鎓溴化物、N-丁基-N-甲基嗎啉鎓碘化物、N-烯丙基-N-甲基嗎啉鎓溴化物、N-甲基-N-苄基
哌啶鎓氯化物、N-甲基-N-苄基哌啶鎓溴化物、N,N-二甲基哌啶鎓碘化物、N-甲基-N-乙基哌啶鎓乙酸鹽、N-甲基-N-乙基哌啶鎓碘化物等。
本反應中之表氯醇之使用量係,相對於雙酚化合物(2)之1個羥基,於1莫耳以上,尤其是於2~10莫耳之範圍內使用,鹼之使用量係,相對於雙酚化合物(2)之1個羥基,於0.1~2.0莫耳,尤其是於0.3~1.5莫耳之範圍內使用,路易斯酸或相間轉移觸媒之使用量係,相對於雙酚化合物(2)之1個羥基,於0.01~10莫耳%,尤其是於0.2~5莫耳%之範圍內使用。
又,本反應中,可使用如製造作為中間產物之雙酚化合物(2)之欄中所例示之溶劑。又,亦可將過剩之表氯醇用作溶劑。
本發明之環氧化合物(A),除可加成不飽和一元酸(B)而製作本發明之環氧加成化合物(W),用作後述之鹼性顯影性樹脂組合物及鹼性顯影性感光性樹脂組合物之原料以外,還可與環氧樹脂用之硬化劑組合而用作本發明之環氧樹脂組合物。
本發明之環氧樹脂組合物係包含本發明之環氧化合物(A)及硬化劑之組合物。作為該硬化劑,例如可列舉:二伸乙三胺、三伸乙三胺、四伸乙五胺等多烷基多胺類;1,2-二胺基環己烷、1,4-二胺基-3,6-二乙基環己烷、異佛酮二胺等脂環式多胺類;間苯二甲基二胺、二胺基二苯基甲烷、二胺基二苯基碸等芳香族多胺類等。又可列舉:藉
由常法使該等多胺類,與苯基縮水甘油醚、丁基縮水甘油醚、雙酚A-二縮水甘油醚、雙酚F-二縮水甘油醚等縮水甘油醚類或羧酸之縮水甘油酯類等各種環氧樹脂進行反應而製造之聚環氧加成改質物;藉由常法使該等有機多胺類,與鄰苯二甲酸、間苯二甲酸、二聚酸等羧酸類進行反應而製造之醯胺化改質物;藉由常法使該等多胺類與甲醛等醛類以及苯酚、甲酚、二甲苯酚、第三丁基苯酚、間苯二酚等核中具有至少一個醛化反應性部位之酚類進行反應而製造之曼尼希(Mannich)化改質物等。另外,亦可使用:二氰基二醯胺、酸酐、2-乙基-4-甲基咪唑等咪唑類等之潛在性硬化劑。
本發明之環氧樹脂組合物中,上述硬化劑之含量相對於本發明之環氧化合物(A)100質量份,較好的是1~500質量份,更好的是10~200質量份。
又,本發明之環氧樹脂組合物中視需要可含有:硬化觸媒;單縮水甘油醚類、鄰苯二甲酸二辛酯、鄰苯二甲酸二丁酯、苄醇、煤焦油等反應性或非反應性之稀釋劑(塑化劑);玻璃纖維、碳纖維、纖維素、石英砂、水泥、高嶺土、黏土、氫氧化鋁、膨潤土、滑石、二氧化矽、二氧化矽細粉末、二氧化鈦、碳黑、石墨、氧化鐵、瀝青物質等填充劑或顏料;γ-胺基丙基三乙氧基矽烷、N-β-(胺基乙基)-γ-胺基丙基三乙氧基矽烷、N-β-(胺基乙基)-N'-β-(胺基乙基)-γ-胺基丙基三乙氧基矽烷、γ-苯胺基丙基三乙氧基矽烷、γ-縮水甘油氧基丙基三乙氧基矽烷、β-(3,4-環氧環
己基)乙基三乙氧基矽烷、乙烯基三乙氧基矽烷、N-β-(N-乙烯基苄基胺基乙基)-γ-胺基丙基三乙氧基矽烷、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、γ-氯丙基三甲氧基矽烷、γ-巰基丙基三甲氧基矽烷等矽烷偶合劑;堪地里拉蠟、巴西棕櫚蠟、木蠟、蟲蠟、蜂蠟、羊毛脂、鯨蠟、褐煤蠟、石油蠟、脂肪酸蠟、脂肪酸酯、脂肪酸醚、芳香族酯、芳香族醚等潤滑劑;增稠劑;觸變劑;抗氧化劑;光穩定劑;紫外線吸收劑;阻燃劑;消泡劑;防銹劑;膠體二氧化矽、膠體氧化鋁等常用之添加物;進而亦可併用二甲苯樹脂、石油樹脂等黏著性之樹脂類。於本發明之環氧樹脂組合物中,該等任意之添加物相對於本發明之環氧化合物(A)100質量份,較好的是合計為100質量份以下。
進而,本發明之環氧化合物(A)亦可用作胺基甲酸乙酯改質、二氧化矽改質、磷酸改質、胺改質、(甲基)丙烯酸改質等各種改質品之原料。
除上述用途外,本發明之環氧化合物(A)亦可用於如下之廣範圍用途中:對混凝土、水泥砂漿、各種金屬、皮革、玻璃、橡膠、塑膠、木材、布料、紙張等之塗料或接著劑;包裝用黏著膠帶、黏著標籤、冷凍食品標籤、易剝除標籤、POS(point-of-sale,銷售點)標籤、黏著壁紙、黏著地板材料之黏著劑;銅版紙、輕質塗料紙、拋光塗料紙、塗佈紙板、無碳複製機、含浸紙等加工紙;天然纖維、合成纖維、玻璃纖維、碳纖維、金屬纖維等之收束劑,防散亂劑,加工劑等纖維處理劑;密封材料、水泥混
和劑、防水材料等建築材料;電子/電氣機器用密封劑等。
本發明之環氧加成化合物(W)具有,於上述環氧化合物(A)上,以相對於上述環氧化合物(A)之1個環氧基,不飽和一元酸(B)之羧基為0.1~1.0個的比例,加成上述不飽和一元酸(B)的結構。環氧加成化合物(W)除可用作後述之本發明之鹼性顯影性樹脂組合物及鹼性顯影性感光性樹脂組合物之原料外,亦可用作塗佈用感光性組合物之原料。
上述不飽和一元酸(B)之羧基相對於上述環氧化合物(A)之1個環氧基的比例較好的是0.3~1.0個。
本發明之鹼性顯影性樹脂組合物含有下述光聚合性不飽和化合物中之任一種或兩種以上:使上述環氧加成化合物(W)與多元酸酐(C),以相對於上述環氧加成化合物(W)之1個羥基,酸酐結構為0.1~1.0個的比例,進行酯化反應而獲得的光聚合性不飽和化合物(X);進而視需要以相對於上述環氧加成化合物(W)之1個羥基,環氧基為0.1~1.0個的比例,加成環氧化合物(D)而獲得的光聚合性不飽和化合物(Y);繼而視需要使多元酸酐(E),以相對於上述環氧加成化合物(W)之1個羥基,酸酐結構為0.1~1.0的比例,進行酯化反應而獲得的光聚合性不飽和化合物(Z)。藉由適當區分使用該等光聚合性不飽和化合物(X)、(Y)及(Z),使得容易調整鹼性顯影性組合物之酸價,故而可用於配合較好的顯影時間。
相對於上述環氧加成化合物(W)之1個羥基,上述多元酸
酐(C)之酸酐結構之比例較好的是0.3~0.95個,上述環氧化合物(D)之環氧基之比例較好的是0.3~0.9個,上述多元酸酐(E)之酸酐結構之比例較好的是0.3~0.7個。
製備本發明之鹼性顯影性樹脂組合物時所使用之不飽和一元酸(B),係用來提高該鹼性顯影性樹脂組合物之靈敏度,例如可列舉:丙烯酸、甲基丙烯酸、丁烯酸、肉桂酸、山梨酸、甲基丙烯酸/順丁烯二酸羥乙酯、丙烯酸/順丁烯二酸羥乙酯、甲基丙烯酸/順丁烯二酸羥丙酯、丙烯酸/順丁烯二酸羥丙酯、二環戊二烯/順丁烯二酸酯、或具有1個羧基及2個以上(甲基)丙烯醯基之多官能(甲基)丙烯酸酯等。
上述具有1個羧基及2個以上(甲基)丙烯醯基之多官能(甲基)丙烯酸酯,例如可藉由使1分子中具有1個羥基及2個以上(甲基)丙烯醯基之多官能(甲基)丙烯酸酯與二元酸酐或羧酸進行反應而獲得。
作為上述具有1個羧基及2個以上(甲基)丙烯醯基之多官能(甲基)丙烯酸酯,例如可列舉下述[化11]~[化13]所示之化合物。
作為用於獲得本發明之鹼性顯影性樹脂組合物之多元酸酐(C),例如可列舉:琥珀酸酐、順丁烯二酸酐、偏苯三甲酸酐、鄰苯二甲酸酐、甲基四氫鄰苯二甲酸酐、四氫鄰苯二甲酸酐、耐地酸酐、甲基耐地酸酐、三烷基四氫鄰苯二甲酸酐、六氫鄰苯二甲酸酐、三烷基四氫鄰苯二甲酸酐-順丁烯二酸酐加成物、十二琥珀酸酐、甲基雙環庚烯二甲酸酐、甲基六氫鄰苯二甲酸酐等單酐;3,3',4,4'-聯苯四羧酸二酐、3,3',4,4'-二苯基四磺酸二酐、4,4'-氧基二鄰苯二甲酸二酐、2,3,5-三羧基環戊基乙酸二酐、1,2,3,4-環戊烷四羧酸二酐、均苯四甲酸酐、2,2'-3,3'-二苯甲酮四羧酸酐、5-(2,5-二氧代四氫呋喃基)-3-甲基-3-環己烯-1,2-二羧酸酐、3,3'-4,4'-二苯甲酮四羧酸酐、乙二醇雙偏苯三甲酸酐酯、內消旋丁烷-1,2,3,4-四羧酸酐等二酐;甘油三偏苯三甲酸酐酯等三酐;該等之中,較好的是二酐或二酐與單酐之組合。
作為製備本發明之鹼性顯影性樹脂組合物時所使用之環氧化合物(D),例如可列舉:單官能環氧化合物、多官能環氧化合物或本發明之環氧化合物(A)。上述單官能環氧化合物係用來調整該鹼性顯影性樹脂組合物之酸價,例如可列舉:甲基丙烯酸縮水甘油酯、甲基縮水甘油醚、乙基縮水甘油醚、丙基縮水甘油醚、異丙基縮水甘油醚、丁基縮水甘油醚、異丁基縮水甘油醚、第三丁基縮水甘油醚、戊基縮水甘油醚、己基縮水甘油醚、庚基縮水甘油醚、辛基縮水甘油醚、壬基縮水甘油醚、癸基縮水甘油醚、十一烷基縮水甘油醚、十二烷基縮水甘油醚、十三烷基縮水甘油醚、十四烷基縮水甘油醚、十五烷基縮水甘油醚、十六烷基縮水甘油醚、2-乙基己基縮水甘油醚、烯丙基縮水甘油醚、炔丙基縮水甘油醚、對甲氧基乙基縮水甘油醚、苯基縮水甘油醚、對甲氧基縮水甘油醚、對丁基苯酚縮水甘油醚、甲苯基縮水甘油醚、2-甲基甲苯基縮水甘油醚、4-壬基苯基縮水甘油醚、苄基縮水甘油醚、對異丙苯基苯基縮水甘油醚、三苯甲基縮水甘油醚、甲基丙烯酸2,3-環氧丙酯、環氧化大豆油、環氧化亞麻仁油、丁酸縮水甘油酯、一氧化乙烯基環己烷、1,2-環氧基-4-乙烯基環己烷、氧化苯乙烯、氧化蒎烯、氧化甲基苯乙烯、氧化環己烯、氧化丙烯、下述[化14]~[化17]所示之化合物等。
上述多官能環氧化合物係用來使上述光聚合性不飽和化合物之分子量增大,從而調整顯影速度,例如,可使用雙酚型環氧化合物及縮水甘油醚類。
作為上述雙酚型環氧化合物,除亞烷基雙酚聚縮水甘油醚型環氧樹脂之外,亦可使用氫化雙酚型環氧化合物等雙酚型環氧化合物。
作為上述縮水甘油醚類,例如可列舉:乙二醇二縮水甘油醚、丙二醇二縮水甘油醚、1,4-丁二醇二縮水甘油醚、1,6-己二醇二縮水甘油醚、1,8-辛二醇二縮水甘油醚、1,10-癸二醇二縮水甘油醚、2,2-二甲基-1,3-丙二醇二縮水甘油醚、二乙二醇二縮水甘油醚、三乙二醇二縮水甘油醚、四乙二醇二縮水甘油醚、六乙二醇二縮水甘油醚、1,4-環己烷二甲醇二縮水甘油醚、1,1,1-三(縮水甘油氧基甲基)丙烷、1,1,1-三(縮水甘油氧基甲基)乙烷、1,1,1-三
(縮水甘油氧基甲基)甲烷、1,1,1,1-四(縮水甘油氧基甲基)甲烷。
除此之外,上述多官能環氧化合物亦可使用:苯酚酚醛清漆型環氧化合物、聯苯酚醛清漆型環氧化合物、甲酚酚醛清漆型環氧化合物、雙酚A酚醛清漆型環氧化合物、二環戊二烯酚醛清漆型環氧化合物等酚醛清漆型環氧化合物;3,4-環氧基-6-甲基環己基甲基-3',4'-環氧基-6'-甲基環己烷羧酸酯、3,4-環氧環己基甲基-3',4'-環氧環己烷羧酸酯、1-環氧乙基-3,4-環氧環己烷等脂環式環氧化合物;鄰苯二甲酸二縮水甘油酯、四氫鄰苯二甲酸二縮水甘油酯、二聚酸縮水甘油酯等縮水甘油酯類;四縮水甘油基二胺基二苯基甲烷、三縮水甘油基-對胺基苯酚、N,N-二縮水甘油基苯胺等縮水甘油基胺類;1,3-二縮水甘油基-5,5-二甲基乙內醯脲、三縮水甘油基異氰尿酸酯等雜環式環氧化合物;二氧化二環戊二烯等二氧化物;萘型環氧化合物、三苯基甲烷型環氧化合物、二環戊二烯型環氧化合物等。
作為視需要而用於獲得本發明之鹼性顯影性樹脂組合物的多元酸酐(E),可使用作為上述多元酸酐(C)所列舉者。
可重複進行於具有使上述(A)~(E)之各成分反應而獲得之結構的光聚合性不飽和化合物上,進一步加成環氧化合物(D),然後與多元酸酐(E)進行酯化的操作,又,亦可於具有使(A)~(E)之各成分反應而獲得之結構的光聚合性不飽和化合物上,進一步加成環氧化合物(D)後,代替多元酸酐(E)而與內酯化合物進行酯化。
具有使上述(A)~(E)之各成分反應而獲得之結構的光聚合性不飽和化合物(X)、(Y)或(Z)之含量較好的是,其含量占本發明之鹼性顯影性樹脂組合物之1~70質量%,更好的是3~30質量%,固形物含量之酸價較好的是20~100 mg.KOH/g之範圍,更好的是50~100 mg.KOH/g之範圍。
除上述光聚合性不飽和化合物之外,本發明之鹼性顯影性樹脂組合物中亦可含有溶劑,例如於光聚合性不飽和化合物之含量為上述較好範圍之情形時,光聚合性不飽和化合物以外之剩餘部分可使用溶劑。作為該溶劑之具體例,可列舉後述之作為鹼性顯影性感光性樹脂組合物中所使用之溶劑而例示者。又,可不除去由(A)~(E)成分合成上述光聚合性不飽和化合物時所使用之溶劑,而直接包含於本發明之鹼性顯影性樹脂組合物中。又,(A)~(E)中之各成分可使用一種,或將兩種以上混合使用。
本發明之鹼性顯影性樹脂組合物主要與光聚合起始劑(F)及溶劑混合,而用作鹼性顯影性感光性樹脂組合物。
以下,基於較好之實施形態,對上述鹼性顯影性感光性樹脂組合物(以下,亦稱作本發明之鹼性顯影性感光性樹脂組合物)加以說明。
本發明之鹼性顯影性感光性樹脂組合物係於含有上述光聚合性不飽和化合物的本發明之鹼性顯影性樹脂組合物中,至少含有光聚合起始劑(F)所得者。
於本發明之鹼性顯影性感光性樹脂組合物中,對於上述光聚合性不飽和化合物之含量而言,以於自鹼性顯影性感
光性樹脂組合物除去溶劑後之總固形物含量的合計質量中所占之比例計,較好的是50~90質量%,更好的是60~80質量%。
作為上述光聚合起始劑(F),可使用先前已知之化合物,例如可列舉:過氧化苯甲醯、2,2'-偶氮二異丁腈、二苯甲酮、苯基聯苯酮、1-羥基-1-苯甲醯基環己烷、苯偶醯、苯偶醯二甲基縮酮、1-苄基-1-二甲基胺基-1-(4'-嗎啉基苯甲醯基)丙烷、2-嗎啉基-2-(4'-甲基巰基)苯甲醯基丙烷、噻噸酮、1-氯-4-丙氧基噻噸酮、異丙基噻噸酮、二乙基噻噸酮、乙基蒽醌、4-苯甲醯基-4'-甲基二苯硫醚、安息香丁醚、2-羥基-2-苯甲醯基丙烷、2-羥基-2-(4'-異丙基)苯甲醯基丙烷、4-丁基苯甲醯基三氯甲烷、4-苯氧基苯甲醯基二氯甲烷、苯甲醯基甲酸甲酯、1,7-雙(9'-吖啶基)庚烷、9-正丁基-3,6-雙(2'-嗎啉基異丁醯基)咔唑、2-甲基-1-[4-(甲硫基)苯基]-2-嗎啉基-1-丙酮、對甲氧基苯基-2,4-雙(三氯甲基)-均三嗪、2-甲基-4,6-雙(三氯甲基)-均三嗪、2-苯基-4,6-雙(三氯甲基)-均三嗪、2-萘基-4,6-雙(三氯甲基)-均三嗪、2-(對丁氧基苯乙烯基)-均三嗪、2-(對丁氧基苯乙烯基)-5-三氯甲基-1,3,4-二唑、9-苯基吖啶、9,10-二甲基苯并啡嗪、二苯甲酮/米其勒酮、六芳基聯咪唑/巰基苯并咪唑、噻噸酮/胺、雙(2,4,6-三甲基苯甲醯基)苯基氧化膦,以及日本專利特開2000-80068號公報、日本專利特開2001-233842號公報、日本專利特開2005-97141號公報、日本專利特表2006-516246號公報、日本專利第3860170號公
報、日本專利第3798008號公報、WO 2006/018973號公報中揭示之化合物等。該等之中,較好的是以下述通式(a)或(c)所表示之化合物。
於本發明之鹼性顯影性感光性樹脂組合物中,對於上述光聚合起始劑(F)之含量而言,以於自鹼性顯影性感光性樹脂組合物除去溶劑後的總固形物含量之合計質量中所占之比例計,較好的是0.1~40質量%,更好的是1.0~10質量%。又,上述光聚合起始劑(F)可使用一種,或將兩種以上混合使用。
作為本發明之鹼性顯影性感光性樹脂組合物中所含之溶劑,通常,只要為可溶解或分散上述各成分之溶劑則無特別限制,例如可列舉:甲基乙基酮、甲基戊基酮、二乙基酮、丙酮、甲基異丙基酮、甲基異丁基酮、環己酮等酮類;***、二烷、四氫呋喃、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷、二丙二醇二甲醚等醚系溶劑;乙酸甲酯、乙酸乙酯、乙酸正丙酯、乙酸異丙酯、乙酸正丁酯等酯系溶劑;乙二醇單甲醚、乙二醇單***、丙二醇單甲醚乙酸酯等溶纖劑系溶劑;甲醇、乙醇、異或正丙醇、異或正丁醇、戊醇等醇系溶劑;苯、甲苯、二甲苯等BTX(benzen-toluene-xylene)系溶劑;己烷、庚烷、辛烷、環己烷等脂肪族烴系溶劑;松節油、D-檸檬烯、蒎烯等萜烯系烴油;
礦油精、Swasol#310(Cosmo Matsuyama Oil股份有限公司)、Solvesso#100(Exxon Chemical股份有限公司)等鏈烷烴系溶劑;四氯化碳、氯仿、三氯乙烯、二氯甲烷等鹵化脂肪族烴系溶劑;氯苯等鹵化芳香族烴系溶劑;卡必醇系溶劑、苯胺、三乙胺、吡啶、乙酸、乙腈、二硫化碳、N,N-二甲基甲醯胺、N-甲基吡咯烷酮等;其中,較好的是酮類或溶纖劑系溶劑。該等溶劑可使用一種,或將兩種以上混合使用。
於本發明之鹼性顯影性感光性樹脂組合物中,將上述溶劑之含量調整為如下既可,即,使總固形物含量於鹼性顯影性感光性樹脂組合物中所占之濃度較好的是5~40質量%,更好的是15~30質量%。
本發明之著色鹼性顯影性感光性樹脂組合物,係於上述鹼性顯影性感光性樹脂組合物中含有色料(G)所得者。
作為本發明之著色鹼性顯影性感光性樹脂組合物中用作色料(G)的顏料,可採用先前製造彩色濾光片時所使用的公知之顏料中之任一種。以下,以顏料索引(C.I.)編號來表示有機顏料之具體例。再者,下述一覽中,「x」表示可自C.I.編號中任意選擇之整數。
.藍色顏料:<C.I>1,1:2,1:x,9:x,15,15:1,15:2,15:3,15:4,15:5,15:6,16,24,24:x,56,60,61,62
.綠色顏料:<C.I>1,1:x,2,2:x,4,7,10,36
.橙色顏料:<C.I>2,5,13,16,17:1,31,34,36,38,43,46,48,49,51,52,59,60,61,62,64
.紅色顏料:<C.I>1,2,3,4,5,6,7,9,10,14,17,22,23,31,38,41,48:1,48:2,48:3,48:4,49,49:1,49:2,52:1,52:2,53:1,57:1,60:1,63:1,66,67,81:1,81:3,81:x,83,88,90,112,119,122,123,144,146,149,166,168,169,170,171,172,175,176,177,178,179,184,185,187,188,190,200,202,206,207,208,209,210,216,224,226
.紫色顏料:<C.I>1,1:x,3,3:3,3:x,5:1,19,23,27,32,42
.黃色顏料:<C.I>1,3,12,13,14,16,17,24,55,60,65,73,74,81,83,93,95,97,98,100,101,104,106,108,109,110,113,114,116,117,119,120,126,127,128,129,138,139,150,151,152,153,154,156,175
又,作為黑色顏料,可列舉:三菱化學公司製造之碳黑(Carbon Black)#2400、#2350、#2300、#2200、#1000、#980、#970、#960、#950、#900、#850、MCF88、#650、MA600、MA7、MA8、MA11、MA100、MA220、IL30B、IL31B、IL7B、IL11B、IL52B、#4000、#4010、#55、#52、#50、#47、#45、#44、#40、#33、#32、#30、#20、#10、#5、CF9、#3050、#3150、#3250、#3750、#3950,Dia black A、Diablack N220M、Diablack N234、Diablack
I、Diablack LI、Diablack LH、Diablack N339、Diablack SH、Diablack SHA、Diablack LH、Diablack H、Diablack HA、Diablack SF、Diablack N550M、Diablack E、Diablack G、Diablack R、Diablack N760M、Diablack LR;Cancarb公司製造之碳黑Thermax N990、N991、N907、N908、N990、N991、N908;Asahi Carbon公司製造之碳黑Asahi#80、Asahi#70、Asahi#70L、Asahi F-200、Asahi#66、Asahi#66U、Asahi#50、Asahi#35、Asahi#15、Asahi Thermal;Degussa公司製造之碳黑ColorBlackFw200、ColorBlackFw2、ColorBlackFw2V、ColorBlackFw1、ColorBlackFw18、ColorBlackS170、ColorBlackS160、SpecialBlack6、SpecialBlack5、SpecialBlack4、SpecialBlack4A、SpecialBlack250、SpecialBlack350、PrintexU、PrintexV、Printex140U、Printex140V(均為商品名)等。
作為其他顏料,亦可使用:米洛麗藍、氧化鐵、酸化鈦、碳酸鈣、碳酸鎂、二氧化矽、氧化鋁、鈷系、錳系、滑石、鉻酸鹽、亞鐵氰化物、各種金屬硫酸鹽、硫化物、硒化物、磷酸鹽群青、鐵藍、鈷藍、天藍、鉻綠、翡翠綠、鈷綠等無機顏料。該等顏料可使用一種,或將兩種以上混合使用。
作為可用作上述色料(G)之染料,可列舉偶氮染料、蒽醌染料、靛染料、三芳基甲烷染料、二苯并哌喃染料、茜素染料、吖啶染料、二苯乙烯染料、噻唑染料、萘酚染料、喹啉染料、硝基染料、吲達胺染料、嗪染料、酞菁
染料、花青染料等染料等,該等染料可使用一種,或將兩種以上混合使用。
於本發明之著色鹼性顯影性感光性樹脂組合物中,對於上述色料(G)之含量而言,以於自著色鹼性顯影性感光性樹脂組合物除去溶劑後之總固形物含量的總質量中所占之比例計,較好的是0.5~70質量%,更好的是5~60質量%。
本發明之鹼性顯影性樹脂組合物、鹼性顯影性感光性樹脂組合物及著色鹼性顯影性感光性樹脂組合物中,可進一步併用具有不飽和鍵之單體、鏈轉移劑、界面活性劑等。
作為上述具有不飽和鍵之單體,可列舉:丙烯酸-2-羥乙酯、丙烯酸-2-羥丙酯、丙烯酸異丁酯、丙烯酸正辛酯、丙烯酸異辛酯、丙烯酸異壬酯、丙烯酸十八烷基酯、丙烯酸甲氧基乙酯、丙烯酸二甲基胺基乙酯、丙烯酸鋅、1,6-己二醇二丙烯酸酯、三羥甲基丙烷三丙烯酸酯、甲基丙烯酸-2-羥乙酯、甲基丙烯酸-2-羥丙酯、甲基丙烯酸丁酯、甲基丙烯酸第三丁酯、甲基丙烯酸環己酯、三羥甲基丙烷三甲基丙烯酸酯、二季戊四醇五丙烯酸酯、二季戊四醇六丙烯酸酯、季戊四醇四丙烯酸酯、季戊四醇三丙烯酸酯、三環癸烷二甲醇二丙烯酸酯等。
於本發明之鹼性顯影性感光性樹脂組合物中,對於上述具有不飽和鍵之單體含量而言,以於自鹼性顯影性感光性樹脂組合物除去溶劑後之總固形物含量的總質量中所占之比例計,較好的是0.01~20質量%,更好的是0.1~10質量%。該等具有不飽和鍵之單體可使用一種,亦可將兩種以
上混合使用。
作為上述鏈轉移劑,可列舉:硫代乙醇酸、硫代蘋果酸、硫代水楊酸、2-巰基丙酸、3-巰基丙酸、3-巰基酪酸、N-(2-巰基丙醯基)甘胺酸、2-巰基煙鹼酸、3-[N-(2-巰基乙基)胺甲醯基]丙酸、3-[N-(2-巰基乙基)胺基]丙酸、N-(3-巰基丙醯基)丙胺酸、2-巰基乙磺酸、3-巰基丙磺酸、4-巰基丁磺酸、十二烷基(4-甲硫基)苯醚、2-巰基乙醇、3-巰基-1,2-丙二醇、1-巰基-2-丙醇、3-巰基-2-丁醇、巰基苯酚、2-巰基乙胺、2-巰基咪唑、2-巰基-3-吡啶酚、2-巰基苯并噻唑、巰基乙酸、三羥甲基丙烷三(3-巰基丙酸酯)、季戊四醇四(3-巰基丙酸酯)等巰基化合物,將該巰基化合物氧化而獲得之二硫化物;碘乙酸、碘丙酸、2-碘乙醇、2-碘乙磺酸、3-碘丙磺酸等碘化烷基化合物。該等鏈轉移劑可使用一種,或將兩種以上混合使用。
作為上述界面活性劑,可使用全氟烷基磷酸酯、全氟烷基羧酸鹽等氟系界面活性劑,高級脂肪酸鹼鹽、烷基磺酸鹽、烷基硫酸鹽等陰離子系界面活性劑,高級胺氫鹵酸鹽、四級銨鹽等陽離子系界面活性劑,聚乙二醇烷基醚、聚乙二醇脂肪酸酯、山梨糖醇酐脂肪酸酯、脂肪酸單甘油酯等非離子界面活性劑,兩性界面活性劑,聚矽氧系界面活性劑等界面活性劑,該等界面活性劑可使用一種,或將兩種以上混合使用。
藉由於本發明之鹼性顯影性樹脂組合物、鹼性顯影性感光性樹脂組合物及著色鹼性顯影性感光性樹脂組合物中,
進一步使用熱塑性有機聚合物,可改善硬化物之特性。作為該熱塑性有機聚合物,例如可列舉:聚苯乙烯、聚甲基丙烯酸甲酯、甲基丙烯酸甲酯-丙烯酸乙酯共聚物、聚(甲基)丙烯酸、苯乙烯-(甲基)丙烯酸共聚物、(甲基)丙烯酸-甲基丙烯酸甲酯共聚物、聚乙烯丁醛、纖維素酯、聚丙烯醯胺、飽和聚酯等。該等熱塑性有機聚合物可使用一種,或將兩種以上混合使用。
又,可視需要於本發明之鹼性顯影性樹脂組合物、鹼性顯影性感光性樹脂組合物及著色鹼性顯影性感光性樹脂組合物中,添加苯甲醚、對苯二酚、鄰苯二酚、第三丁基鄰苯二酚、硫二苯胺等熱聚合抑制劑;塑化劑;助黏劑;填充劑;消泡劑;分散劑;勻平劑;矽烷偶合劑;阻燃劑等常用之添加物。該等添加物可使用一種,或將兩種以上混合使用。
本發明之鹼性顯影性感光性樹脂組合物及著色鹼性顯影性感光性樹脂組合物,可藉由旋轉塗佈機、棒塗機、輥塗機、簾塗機、各種絲網印刷、噴墨印刷、浸漬等公知之機構,而應用於金屬、紙張、塑膠等支持基體上。又,亦可暫時施加於薄膜等支持基體上,然後轉印至其他支持基體上,對其應用方法並無限制。
本發明之(著色)鹼性顯影性感光性樹脂組合物主要與上述溶劑、上述光聚合起始劑及色料混合,而用作(著色)鹼性顯影性感光性樹脂組合物,對該(著色)鹼性顯影性感光性樹脂組合物之用途並無特別限制,可用於:光硬化性塗
料,光硬化性接著劑,印刷板、印刷電路板用光阻劑,以及形成液晶顯示器、電漿顯示器、電致發光面板、視訊攝影機等中所使用之液晶分割配向控制用突起或彩色濾光片之像素部等各種用途。
又,作為使本發明之鹼性顯影性感光性樹脂組合物及著色鹼性顯影性感光性樹脂組合物硬化時所使用的活性光之光源,可使用發出波長為300~450 nm之光的光源,例如可使用超高壓水銀燈、水銀蒸汽電弧燈、碳弧燈、氙弧燈等。
以下,揭示實施例及比較例對本發明進行更詳細之說明,但本發明並不限定於該等實施例等。
再者,實施例1-1~1-3表示本發明之環氧化合物(A)及環氧加成化合物(W)之製造例,使用例1表示使用本發明之環氧化合物(A)之環氧樹脂組合物之實施例,實施例2-1~2-7表示本發明之鹼性顯影性樹脂組合物之製造例,實施例3-1~3-7表示本發明之鹼性顯影性感光性樹脂組合物之實施例,實施例4-1~4-7表示本發明之著色鹼性顯影性感光性樹脂組合物之實施例。
<步驟1>1,1-雙(4-羥基苯基)二氫茚(雙酚化合物(2),以下,亦稱作化合物P-1)之製造
[化21]
化合物P-1
於安裝有攪拌裝置、氮氣導入管、回流冷卻管及溫度計之2 L四口燒瓶中,於氮氣環境下,投入1-二氫茚酮200 g、苯酚855 g,於40℃以下緩慢滴加硫酸59.4 g、繼而3-巰基丙酸16.1 g。滴加後升溫,於55℃下反應20小時,然後添加乙酸乙酯300 g及48重量%氫氧化鈉水溶液50.4 g加以中和,過濾所析出之晶體,獲得粗產物224 g。將該粗產物溶解於乙酸乙酯1450 g中,於以5重量%乙酸銨水溶液500 g加以清洗、分液直至有機層之pH值變成4~5的有機層中,加入無水硫酸鎂50 g,進行乾燥。餾去濾液中之乙酸乙酯,於晶體析出時添加甲苯400 g,進行晶析。濾取該晶體,用甲苯進行分散清洗後,於40℃下進行真空乾燥,獲得白色晶體135 g(產率為30%)。該白色晶體之熔點為215℃,對該白色晶體進行各種分析,結果確認該白色晶體為目標化合物P-1。
(分析結果)
(1)1
H-NMR之化學位移:(ppm)
8.21(s:2H),7.29~7.23(m:1H),7.20~7.13(m:2H),7.05~7.00(m:1H),6.97(d:4H),6.72(d:4H),2.81(t:2H),2.72(t:2H)
(2)IR(Infrared Ray,紅外線)之吸收(cm-1
)
3300,3066,3021,2965,2942,2912,2861,2861,2844,
1610,1595,1508,1469,1457,1437,1362,1312,1296,1238,1216,1176,1158,1135,1113,1087,1039,1011,966,937,899,855,825,772,754,724,675
<步驟2>化合物a-1(上述通式(I)所表示之環氧化合物(A))之製造
於安裝有攪拌裝置、氮氣導入管、回流冷卻管及溫度計之2 L四口燒瓶中,於氮氣環境下,投入上述<步驟1>中所得的作為雙酚化合物(2)之化合物P-1 29.2 g及表氯醇142 g,添加苄基三乙基氯化銨0.412 g,於74℃下攪拌14小時。繼而降溫至60℃,於13000 Pa之減壓下,滴加48重量%氫氧化鈉水溶液16.1 g,一面使與水共沸之表氯醇返回至系統內一面攪拌2.5小時。於表氯醇停止與水共沸之時刻,緩慢升溫並減壓,於120℃下對表氯醇進行2小時餾去。恢復至常壓,添加甲苯205 g,進行3次水洗。於油水分離之有機層中添加48重量%氫氧化鈉水溶液3.99 g、苄基三乙基氯化銨0.412 g及水0.870 g,於80℃下攪拌2.5小時。其後冷卻至室溫,加入10重量%磷酸二氫鈉水溶液0.692 g加以中和,進行3次水洗。用矽藻土對油水分離所獲得之有機層進行過濾,餾去溶劑,獲得淡黃色黏稠物36.6 g(產率為
92%,環氧當量為212)。藉由各種分析,確認該淡黃色黏稠物為目標化合物a-1。
(分析結果)
(1)1
H-NMR之化學位移:(ppm)
7.30~7.26(m:1H),7.22~7.16(m:2H),7.07(d:4H),7.05~7.01(m:1H),6.87(d:4H),4.31(d:1H),4.28(d:1H),3.87(d:1H),3.84(d:IH),3.32~3.27(m:2H),2.89(t:2H),2.85(t:2H),2.79~2.71(m:4H)
(2)IR之吸收(cm-1
)
3061,3036,3001,2928,2875,2844,1712,1606,1579,1508,1472,1456,1432,1414,1347,1295,1246,1183,1158,1133,1118,1086,1032,970,915,861,828,771,756,730
<步驟3>化合物w-1(環氧加成化合物(W))之製造。
投入作為環氧化合物(A)之上述<步驟2>中所得之化合物a-1 149 g、作為不飽和一元酸(B)之丙烯酸(以下,亦稱作化合物b)37.3 g、2,6-二-第三丁基對甲酚0.398 g、四丁基氯化銨0.909 g及丙二醇-1-單甲醚-2-乙酸酯(以下,亦稱作PGMAc)54.5 g,於90℃下攪拌1小時、於105℃下攪拌1小時、及於120℃下攪拌17小時,以PGMAc溶液之形式獲得目標物。對該PGMAc溶液進行各種分析,確認其為目標化合物w-1(酸價(固形物含量)為1.06 mg.KOH/g)。化合物w-1具有於化合物a-1上,以相對於化合物a-1之1個環氧基,化合物b之羧基為1.0個之比率加成化合物b的結構。
IR之吸收(cm-1
)
3449,3064,3036,2944,2877,2841,1725,1634,1608,1580,1508,1472,1457,1408,1373,1295,1247,1183,1130,1117,1063,1048,1011,984,938,900,827,810,771,756,731,667
<步驟1>1,1-雙(4-羥基苯基)-3-苯基二氫茚(雙酚化合物(2),以下亦稱作P-2)之製造
於安裝有攪拌裝置、氮氣導入管、回流冷卻管及溫度計之1 L四口燒瓶中,於氮氣環境下,投入3-苯基-1-二氫茚酮93.6 g、苯酚254 g、3-巰基丙酸2.4 g,滴加硫酸17.7 g。於60℃下反應10小時後,添加水300 g及乙酸乙酯800 g。於其中添加48%氫氧化鈉水溶液直至變成中性,然後,使用20%食鹽水300 g進行清洗。將該有機層之乙酸乙酯餾去,添加甲苯200 g,回收由此而產生之沈澱,獲得粗產物135 g。使用乙酸乙酯與甲苯之混合溶劑對該粗產物進行晶析,獲得白色晶體110 g(產率為65%)。對該白色晶體進行各種分析,結果確認該白色晶體為目標化合物P-2。
(分析結果)
(1)1
H-NMR之化學位移:(ppm)
9.32(s:1H),9.28(s:1H),7.33(t:2H),7.29~7.19(m:4H),
7.19~7.10(m:1H),7.04(d:1H),6.99(d:2H),6.92(d:2H),6.74(d:1H),6.71~6.64(m:4H),4.15~4.08(m:1H),3.17~3.09(m:1H),2.69~2.60(m:1H)
(2)IR之吸收(cm-1
)
3276,3062,3025,2960,2930,2878,1612,1596,1559,1506,1469,1450,1375,1350,1308,1231,1180,1150,1113,1073,1012,912,836,763,754,733
<步驟2>化合物a-2(上述通式(I)所表示之環氧化合物(A))之製造
於安裝有攪拌裝置、氮氣導入管、回流冷卻管及溫度計之1 L四口燒瓶中,於氮氣環境下,投入作為雙酚化合物(2)之化合物P-2 100 g及表氯醇392 g,添加苄基三乙基氯化銨1.20 g,於78度下攪拌14小時。繼而降溫至60度,於13000 Pa之減壓下,滴加24重量%氫氧化鈉水溶液44.3 g,一面使共沸之表氯醇返回至系統內一面攪拌30分鐘。餾去表氯醇及水,添加甲苯400 g,進行水洗。於該溶液中滴加24重量%氫氧化鈉水溶液2.2 g,於80℃下攪拌2小時後,冷卻至室溫,用3重量%磷酸二氫鈉水溶液加以中
和,進行水洗。餾去溶劑,獲得黃色固體103 g(產率為79%,環氧當量為254)。對該黃色固體進行各種分析,結果確認該黃色晶體為目標化合物a-2。
(分析結果)
(1)1
H-NMR之化學位移:(ppm)
7.35(t:2H),7.28(d:3H),7.23~7.15(m:2H),7.15~7.08(m:4H),7.06(d:1H),6.92(d:1H),6.88~6.80(m:4H),4.25~4.12(m:3H),4.0~3.91(m:2H),3.39~3.31(m:2H),3.20~3.11(m:1H),2.94~2.83(m:3H),2.77~2.73(m:2H)
(2)IR之吸收(cm-1
)
3549,3028,2925,2871,1699,1606,1579,1541,1503,1471,1455,1396,1295,1246,1183,1134,1036,914,830,757,702
<步驟1>1,1-雙(4-羥基苯基)-3,5-二苯基二氫茚(雙酚化合物(2),以下亦稱作P-3)之製造
於安裝有攪拌裝置、氮氣導入管、回流冷卻管及溫度計之1 L四口燒瓶中,於氮氣環境下,投入3,5-二苯基-1-二氫茚酮92.8 g、苯酚184 g、3-巰基丙酸1.73 g,滴加硫酸12.8 g。於60℃下反應15小時後,添加水300 g及乙酸乙酯
800 g。於其中添加48%氫氧化鈉水溶液直至變成中性,然後,使用20%食鹽水300 g進行清洗。將該有機層之乙酸乙酯餾去,添加甲苯200 g,回收由此而產生之沈澱,獲得粗產物112.4 g。使用乙酸乙酯與甲苯之混合溶劑對該粗產物進行晶析,獲得白色晶體61.7 g(產率為42%)。對該白色晶體進行各種分析,結果確認該白色晶體為目標化合物P-3。
(分析結果)
(1)1
H-NMR之化學位移:(ppm)
9.32(s:1H),9.28(s:1H),7.55~7.48(m:3H),7.41~7.25(m:8H),7.14(d:1H),7.06(d:2H),6.96~6.93(m:3H),6.70(t:4H),4.22~4.15(m:1H),3.23~3.15(m:1H),2.68(t:1H)
(2)IR之吸收(cm-1
)
3592,3293,3025,2955,2930,2876,1608,1595,1509,1474,1441,1368,1350,1298,1252,1236,1177,1112,1012,901,864,831,765,703
<步驟2>化合物a-3(上述通式(1)所表示之環氧化合物(A))之製造
於安裝有攪拌裝置、氮氣導入管、回流冷卻管及溫度計
之1 L四口燒瓶中,於氮氣環境下,投入作為雙酚化合物(2)之化合物P-3 55.0 g及表氯醇179 g,添加苄基三乙基氯化銨0.28 g,於78度下攪拌14小時。繼而降溫至60度,於13000 Pa之減壓下,滴加48重量%氫氧化鉀水溶液28.1 g,一面使共沸之表氯醇返回至系統內一面攪拌2小時。餾去表氯醇及水,添加甲苯400 g,進行水洗。於該甲苯溶液中添加48重量%氫氧化鉀水溶液4.0 g,於80℃下攪拌2小時後,冷卻至室溫,用5重量%磷酸二氫鈉水溶液加以中和,進行水洗。餾去溶劑,使用甲苯與2-丙醇之混合溶劑對所獲得之黏性液體進行晶析,獲得黃白色晶體44.2 g(產率為76%,環氧當量為292)。進行各種分析,結果確認該黃白色晶體為目標物a-3。
(分析結果)
(1)1
H-NMR之化學位移:(ppm)
7.52~7.45(m:3H),7.40~7.24(m:8H),7.20~7.12(m:6H),6.89~6.83(m:4H),4.26~4.18(m:3H),4.00~3.94(m:2H),3.40~3.33(m:2H),3.23~3.17(m:1H),2.94~2.86(m:3H),2.79~2.74(m:2H)
(2)IR之吸收(cm-1
)
3466,3060,3029,2936,2871,1606,1581,1508,1476,1454,1411,1347,1298,1247,1182,1076,1037,968,915,831,764,702
將環氧化合物a-1 3.5 g、PGMAc 1.5 g、甲基四氫鄰苯二甲酸酐(以下,亦稱作MTHPA)2.74 g及2-乙基-4-甲基咪
唑(以下,亦稱作2E4MZ)0.06 g混合,製作使用例1之環氧樹脂組合物。將該環氧樹脂組合物3 g以直徑7 cm均勻塗佈於玻璃板上,於80℃下加熱60分鐘,進而於150℃下加熱120分鐘使之硬化而獲得硬化物。將所得硬化物於80℃之熱水浴中浸漬60分鐘,求出質量增加率(%)[吸水率]。將該等之結果示於[表1]。
將1,1-雙[4-(2,3-環氧丙氧基)苯基]-1-(4-聯苯基)-1-環己基甲烷(以下,亦稱作化合物E-BC)3.5 g、PGMAc 1.5 g、MTHPA 2.08 g及2E4MZ 0.06 g混合,製作比較使用例1之環氧樹脂組合物。將該環氧樹脂組合物3 g以直徑7 cm均勻塗佈於玻璃板上,於80℃下加熱60分鐘,然後於150℃下加熱120分鐘使之硬化而獲得硬化物。將所得硬化物於80℃之熱水浴中浸漬60分鐘,求出質量增加率(%)[吸水率]。將該等之結果示於[表1]。
將雙酚A二縮水甘油醚(ADEKA公司製造之EP-4100E,以下亦稱作BisADGE)3.5 g、PGMAc 1.5 g、MTHPA 3.13 g及2E4MZ 0.06 g混合,製作比較使用例2之環氧樹脂組合物。將該環氧樹脂組合物3 g以直徑7 cm均勻塗佈於玻璃板上,於80℃下加熱60分鐘,然後於150℃下加熱120分鐘使之硬化而獲得硬化物。將所得硬化物於80℃之熱水浴中浸漬60分鐘,求出質量增加率(%)[吸水率]。將該等之結果示於[表1]。
投入作為環氧化合物(A)之實施例1-1的<步驟2>中所得之化合物a-1 30.0 g、作為不飽和一元酸(B)之化合物b 7.52 g、2,6-二-第三丁基對甲酚0.080 g、四丁基氯化銨0.183 g及PGMAc 11.0 g,於90℃下攪拌1小時、於105℃下攪拌1小時、及於120℃下攪拌17小時。冷卻至室溫,添加作為多元酸酐(C)之琥珀酸酐(以下,亦稱作化合物c-1)8.11 g、四丁基氯化銨0.427 g及PGMAc 11.1 g,於100℃下攪拌5小時。進而,添加作為環氧化合物(D)之實施例1的<步驟2>中所得之a-1之12.0 g、2,6-二-第三丁基對甲酚0.080 g及PGMAc 0.600 g,於90℃下攪拌90分鐘,於120℃下攪拌5小時後,添加PGMAc 24.0 g,以PGMAc溶液之形式獲得作為目標物之鹼性顯影性樹脂組合物No.1(Mw=4900,Mn=2250,酸價(固形物含量)為47 mg.KOH/g)。所得之鹼性顯影性樹脂組合物No.1含有44.4質量%之作為反應產物之光聚合性不飽和化合物(Y)。
再者,鹼性顯影性樹脂組合物No.1所含有之光聚合性不飽和化合物(Y)係以如下方式獲得者:以相對於環氧加成
化合物(W)之1個羥基,作為(C)成分之化合物c-1之酸酐結構為0.8個、作為(D)成分之化合物a-1之環氧基為0.4個的比例,使環氧加成物(W)與化合物c-1及化合物a-1反應而獲得,其中,上述環氧加成化合物(W)具有於作為(A)成分之化合物a-1上加成作為(B)成分之化合物b之結構。又,上述環氧加成物(W)具有於化合物a-1上,以相對於化合物a-1之1個環氧基,化合物b之羧基為1.0個的比例而加成化合物b的結構。
投入作為環氧化合物(A)之實施例1-1的<步驟2>中所得之化合物a-1 30.0 g、作為不飽和一元酸(B)之化合物b 7.52 g、2,6-二-第三丁基對甲酚0.104 g、四丁基氯化銨0.183 g及PGMAc 11.0 g,於90℃下攪拌1小時、於105℃下攪拌1小時、及於120℃下攪拌17小時。冷卻至室溫,添加作為多元酸酐(C)之3,3',4,4'-聯苯四羧酸二酐(以下,亦稱作化合物c-2)9.24 g及1,2,3,6-四氫鄰苯二甲酸酐(以下,亦稱作化合物c-3)0.154 g、四丁基氯化銨0.427 g及PGMAc 12.1 g,於120℃下攪拌5小時,於90℃下攪拌1小時,於60℃下攪拌2小時及於40℃下攪拌3小時後,添加PGMAc 17.5 g,以PGMAc溶液之形式獲得作為目標物之鹼性顯影性樹脂組合物No.2(Mw=6370,Mn=2570,酸價(固形物含量)為94 mg.KOH/g)。
所得之鹼性顯影性樹脂組合物No.2含有44.5質量%之作為反應產物之光聚合性不飽和化合物(X)。
再者,鹼性顯影性樹脂組合物No.2所含有之光聚合性不飽和化合物(X)係以如下方式獲得:以相對於環氧加成化合物(W)之1個羥基,作為(C)成分之化合物c-2之酸酐結構為0.62個、作為(C)成分之化合物c-3之酸酐結構為0.01個的比例,使環氧加成化合物(W)與化合物c-2及化合物c-3進行酯化反應而獲得,其中上述環氧加成化合物(W)具有於作為(A)成分之化合物a-1上加成作為(B)成分之化合物b之結構。又,上述環氧加成物(W)具有於化合物a-1上,以相對於化合物a-1之1個環氧基,化合物b之羧基為1.0個的比例而加成化合物b的結構。
投入作為環氧化合物(A)之實施例1-1的<步驟2>中所得之化合物a-1 30.0 g、作為不飽和一元酸(B)之化合物b 7.52 g、2,6-二-第三丁基對甲酚0.104 g、四丁基氯化銨0.183 g及PGMAc 11.0 g,於90℃下攪拌1小時,於105℃下攪拌1小時及於120℃下攪拌17小時。冷卻至室溫,添加作為多元酸酐(C)之化合物c-2 7.75 g及化合物c-3 1.69 g、四丁基氯化銨0.427 g及PGMAc 12.1 g,於120℃下攪拌5小時、於90℃下攪拌1小時、於60℃下攪拌2小時、及於40℃下攪拌3小時後,添加PGMAc 17.5 g,以PGMAc溶液之形式獲得作為目標物之鹼性顯影性樹脂組合物No.3(Mw=4590,Mn=2120,酸價(固形物含量)為93 mg.KOH/g)。所得之鹼性顯影性樹脂組合物No.3含有44.5質量%之作為反應產物之光聚合性不飽和化合物(X)。
再者,鹼性顯影性樹脂組合物No.3所含有之光聚合性不飽和化合物(X)係以如下方式獲得:以相對於環氧加成化合物(W)之1個羥基,作為(C)成分之化合物c-2之酸酐結構為0.52個、作為(C)成分之化合物c-3之酸酐結構為0.11個的比例,使環氧加成化合物(W)與化合物c-2及化合物c-3進行酯化反應而獲得,其中,上述環氧加成化合物(W)具有於作為(A)成分之化合物a-1上加成作為(B)成分之化合物b之結構。又,上述環氧加成物(W)具有於化合物a-1上,以相對於化合物a-1之1個環氧基,化合物b之羧基為1.0個的比例而加成化合物b的結構。
投入作為環氧化合物(A)之實施例1-1的<步驟2>中所得之化合物a-1 30.0 g、作為不飽和一元酸(B)之化合物b 7.52 g、2,6-二-第三丁基對甲酚0.080 g、四丁基氯化銨0.183 g及PGMAc 11.0 g,於90℃下攪拌1小時,於105℃下攪拌1小時及於120℃下攪拌17小時。冷卻至室溫,添加作為多元酸酐(C)之化合物c-1 7.10 g及六氫鄰苯二甲酸酐(以下,亦稱作化合物c-4)1.56 g、四丁基氯化銨0.427 g及PGMAc 11.5 g,於100℃下攪拌5小時。其後,冷卻至室溫,添加作為環氧化合物(D)之實施例1的<步驟2>中所得之化合物a-1 15.9 g及2,6-二-第三丁基對甲酚0.087 g,於90℃下攪拌90分鐘、於120℃下攪拌4小時、於100℃下攪拌7小時。然後,添加作為多元酸酐(E)之化合物c-3之3.84 g,於100℃下攪拌3小時,添加PGMAc 25.3 g,以PGMAc溶液之形
式獲得作為目標物之鹼性顯影性樹脂組合物No.4(Mw=6500,Mn=3000,酸價(固形物含量)為58 mg.KOH/g)。所得之鹼性顯影性樹脂組合物No.4含有44.4質量%之作為反應產物之光聚合性不飽和化合物(Z)。
再者,鹼性顯影性樹脂組合物No.4所含有之光聚合性不飽和化合物(Z)係以如下方式獲得:以相對於環氧加成化合物(W)之1個羥基,作為(C)成分之化合物c-1之酸酐結構為0.7個、化合物c-4之酸酐結構為0.1個、作為(D)成分之化合物a-1之環氧基為0.53個、作為(E)成分之化合物c-3之酸酐結構為0.28個的比例,使環氧加成化合物(W)與化合物c-1、化合物c-4、化合物a-1及化合物c-3反應而獲得,其中上述環氧加成化合物(W)具有於作為(A)成分之化合物a-1上加成作為(B)成分之化合物b之結構。又,上述環氧加成物(W)具有於化合物a-1上,以相對於化合物a-1之1個環氧基,化合物b之羧基為1.0個的比例而加成化合物b的結構。
投入作為環氧化合物(A)之實施例1-2的<步驟2>中所得之化合物a-2 18.5 g、作為不飽和一元酸(B)之化合物b 5.37 g、2,6-二-第三丁基對甲酚0.07 g、苄基三乙基氯化銨0.132 g及PGMAc之15.9 g,於120℃下攪拌16小時。冷卻至室溫,投入作為多元酸酐(C)之化合物c-2 5.58 g及化合物c-3 1.90 g,加入苄基三乙基氯化銨0.132 g及PGMAc 9.74 g,於120℃下攪拌5小時、於90℃下攪拌1小時、於60℃下攪
拌2小時、及於40℃下攪拌3小時後,添加PGMAc 12.7 g,以PGMAc溶液之形式獲得作為目標物之鹼性顯影性樹脂組合物No.5(Mw=4200,Mn=2100,酸價(固形物含量)為97 mg.KOH/g)。所得之鹼性顯影性樹脂組合物No.5含有44.6重量%之作為反應產物之光聚合性不飽和化合物(Y)。
再者,鹼性顯影性樹脂組合物No.5所含有之光聚合性不飽和化合物(Y)係以如下方式獲得:以相對於環氧加成化合物(W)之1個羥基,作為(C)成分之化合物c-2之酸酐結構為0.52個、作為(C)成分之化合物c-3之酸酐結構為0.17個的比例,使環氧加成化合物(W)與化合物c-2及c-3反應而獲得,其中,上述具有於作為(A)成分之化合物a-2上加成作為(B)成分之化合物b之結構。又,上述環氧加成物(W)具有於化合物a-2上,以相對於化合物a-2之1個環氧基,化合物b之羧基為1.0個的比例而加成化合物b的結構。
投入作為環氧化合物(A)之實施例1-2的<步驟2>中所得之化合物a-2 13.9 g、作為不飽和一元酸(B)之化合物b 4.03 g、2,6-二-第三丁基對甲酚0.05 g、苄基三乙基氯化銨0.100 g及PGMAc之11.9 g,於120℃下攪拌16小時。冷卻至室溫,投入作為多元酸酐(C)之化合物c-1 4.39 g,加入苄基三乙基氯化銨0.180 g及PGMAc 6.30 g,於100℃下攪拌5小時。冷卻至室溫,添加作為環氧化合物(D)之實施例1-2的<步驟2>中所得之化合物a-2 5.55 g及2,6-二-第三丁基對甲酚0.05 g,於120℃下攪拌8小時後,添加PGMAc之15.8 g,
以PGMAc溶液之形式獲得作為目標物之鹼性顯影性樹脂組合物No.6(Mw=4400,Mn=2000,酸價(固形物含量)為49 mg.KOH/g)。所得之鹼性顯影性樹脂組合物No.6含有44.8重量%之作為反應產物之光聚合性不飽和化合物(Y)。
再者,鹼性顯影性樹脂組合物No.6所含有之光聚合性不飽和化合物(Y)係以如下方式獲得:以相對於環氧加成化合物(W)之1個羥基,作為(C)成分之化合物c-1之酸酐結構為0.80個、作為(D)成分之化合物a-2之環氧基為0.4個的比例,使環氧加成化合物(W)與化合物c-1及a-2反應而獲得,其中,上述環氧加成化合物(W)具有於作為(A)成分之化合物a-2上加成作為(B)成分之化合物b之結構。又,上述環氧加成物(W)具有於化合物a-2上,以相對於化合物a-2之1個環氧基,化合物b之羧基為1.0個的比例而加成化合物b的結構。
投入作為環氧化合物(A)之實施例1-3的<步驟2>中所得之化合物a-3 30.0 g、化合物b 7.56 g、2,6-二-第三丁基對甲酚0.10 g、苄基三乙基氯化銨0.186 g及PGMAc之37.3 g,於120℃下攪拌20小時。冷卻至室溫,投入作為多元酸酐(C)之化合物c-2 6.36 g及化合物c-3 5.49 g、苄基三乙基氯化銨0.434 g及PGMAc 2.86 g,於120℃下攪拌5小時、於90℃下攪拌1小時、於60℃下攪拌2小時、及於40℃下攪拌3小時後,以51.6 g之PGMAc稀釋,以PGMAc溶液之形式獲得作為目標物之鹼性顯影性樹脂組合物No.7(Mw=2820,
Mn=1950,酸價(固形物含量)為96 mg.KOH/g)。所得之鹼性顯影性樹脂組合物No.7含有35.6重量%之作為反應產物之光聚合性不飽和化合物(Y)。
再者,鹼性顯影性樹脂組合物No.7所含有之光聚合性不飽和化合物(Y)係以如下方式獲得:以相對於環氧加成化合物(W)之1個羥基,作為(C)成分之化合物c-2之酸酐結構為0.42個、作為(C)成分之化合物c-3之酸酐結構為0.35個的比例,使環氧加成化合物(W)與化合物c-1及c-3反應而獲得,其中,上述環氧加成化合物(W)具有於作為(A)成分之化合物a-3上加成作為(B)成分之化合物b之結構。又,上述環氧加成物(W)具有於化合物a-3上,以相對於化合物a-3之1個環氧基,化合物b之羧基為1.0個的比例而加成化合物b的結構。
投入化合物E-BC 1695 g、化合物b 443 g、2,6-二-第三丁基對甲酚6 g、四丁基氯化銨11 g及PGMAc 1425 g,於90℃下攪拌1小時、於100℃下攪拌1小時、於110℃下攪拌1小時、及於120℃下攪拌16小時。冷卻至室溫,添加PGMAc 718 g、化合物c-1 482 g及四丁基氯化銨25 g,於100℃下攪拌5小時。進而添加化合物E-BC之508 g及PGMAc之218 g,於90℃下攪拌90分鐘、於120℃下攪拌11小時後,添加PGMAc 1463 g,以PGMAc溶液之形式獲得作為目標物之比較鹼性顯影性樹脂組合物No.1(Mw=4200,Mn=2200,酸價(固形物含量)為53 mg.KOH/g)。
投入化合物E-BC 390 g、化合物b 71.1 g、2,6-二-第三丁基對甲酚1.34 g、四丁基氯化銨1.75 g及PGMAc 108 g,於90℃下攪拌1小時、於100℃下攪拌1小時、於110℃下攪拌1小時、及於120℃下攪拌17小時。冷卻至室溫,添加化合物c-2 59.2 g、化合物c-3 45.2 g、四丁基氯化銨4.08 g及PGMAc 137 g,於120℃下攪拌5小時、於90℃下攪拌1小時、於60℃下攪拌2小時、及於40℃下攪拌3小時後,添加PGMAc 203 g,以PGMAc溶液之形式獲得作為目標物之比較鹼性顯影性樹脂組合物No.2(Mw=3700,Mn=2000,酸價(固形物含量)為91 mg.KOH/g)。
投入9,9-雙[4-(2,3-環氧丙氧基)苯基]茀75.0 g、化合物b 23.8 g、2,6-二-第三丁基對甲酚0.273 g、四丁基氯化銨0.585 g及PGMAc 65.9 g,於90℃下攪拌1小時、於100℃下攪拌1小時、於110℃下攪拌1小時、及於120℃下攪拌14小時。冷卻至室溫,添加化合物c-1 25.9 g、四丁基氯化銨0.427 g及PGMAc 1.37 g,於100℃下攪拌5小時。進而添加9,9-雙[4-(2,3-環氧丙氧基)苯基]茀30.0 g、2,6-二-第三丁基對甲酚0.269 g及PGMAc 1.50 g,於90℃下攪拌90分鐘、於120℃下攪拌4小時後,添加PGMAc 93.4 g,以PGMAc溶液之形式獲得作為目標物之比較鹼性顯影性樹脂組合物No.3(Mw=4190,Mn=2170,酸價(固形物含量)為52 mg.KOH/g)。
投入9,9-雙[4-(2,3-環氧丙氧基)苯基]茀184 g、化合物b 58.0 g、2,6-二-第三丁基對甲酚0.26 g、四丁基氯化銨0.11 g及PGMAc 23.0 g,於120℃下攪拌16小時。冷卻至室溫,添加PGMAc 35 g、化合物c-2 59.0 g及四正丁基溴化銨0.24 g,於120℃下攪拌4小時。進而添加化合物c-3 20.0 g,於120℃下攪拌4小時、於100℃下攪拌3小時、於80℃下攪拌4小時、於60℃下攪拌6小時、於40℃下攪拌11小時後,添加PGMAc 90 g,以PGMAc溶液之形式獲得作為目標物之比較鹼性顯影性樹脂組合物No.4(Mw=5000,Mn=2100,酸價(固形物含量)為93 mg.KOH/g)。
投入BisADGE 154 g、化合物b 59.0 g、2,6-二-第三丁基對甲酚0.26 g、四丁基氯化銨0.11 g及PGMAc 23.0 g,於120℃下攪拌16小時。冷卻至室溫,添加PGMAc 365 g、化合物c-2 67.0 g及四正丁基溴化銨0.24 g,於120℃下攪拌4小時、於100℃下攪拌3小時、於80℃下攪拌4小時、於60℃下攪拌6小時、於40℃下攪拌11小時後,添加PGMAc 90.0 g,以PGMAc溶液之形式獲得作為目標物之比較鹼性顯影性樹脂組合物No.5(Mw=7500,Mn=2100,酸價(固形物含量)為91 mg.KOH/g)。
分別於實施例2-1~2-7中所得之鹼性顯影性樹脂組合物No.1~No.7以及比較例1-1~1-5中所得之比較鹼性顯影性樹脂組合物No.1-1~1-5 44 g中,添加三羥甲基丙烷三丙烯酸酯6.3 g、作為光聚合起始劑(F)之二苯甲酮2.1 g及PGMAc 78 g,充分攪拌,獲得鹼性顯影性感光性樹脂組合物No.1~No.7以及比較鹼性顯影性感光性樹脂組合物No.1~No.5。
以如下方式,對上述實施例3-1~3-7中製備之鹼性顯影性感光性樹脂組合物No.1~No.7、以及比較例2-1~2-5中製備之比較鹼性顯影性感光性樹脂組合物No.1~No.5進行評價。
即,於基板上旋轉塗佈γ-縮水甘油氧基丙基甲基乙氧基矽烷,充分旋轉乾燥後,旋轉塗佈(1300 r.p.m,50秒)上述鹼性顯影性感光性樹脂組合物,加以乾燥。於70℃下進行20分鐘預烤後,塗佈聚乙烯醇5%溶液作為氧阻隔膜。於70℃下乾燥20分鐘後,使用特定之光罩,使用超高壓水銀燈作為光源進行曝光後,於2.5%碳酸鈉溶液中、25℃下浸漬30秒使之顯影,充分水洗。水洗乾燥後,於230℃下烘烤1小時使圖案固著。對所得圖案進行以下評價。結果示於[表2]。
<靈敏度>
將曝光時曝光量為70 mJ/cm2
即充分者設為a,將70
+J/cm2
不充分而100 mJ/cm2
即可曝光者設為b,將100 mJ/cm2
不充分而150 mJ/cm2
即可曝光者設為c。
<析像度>
將曝光顯影時線寬為8 μm以下亦可良好地形成圖案者評為A,將線寬為10 μm即可良好地形成圖案者評為B,將線寬若非30 μm以上則無法良好地形成圖案者評為C。
<密著性>
目視觀察顯影所獲得之圖案之剝落,將完全未觀察到圖案剝落者設為○,將觀察到一部分圖案剝落者設為×。
實施例3-1~3-7之鹼性顯影性感光性樹脂組合物No.1~No.7係高靈敏度且析像度及密著性優異者。
相對於此,比較例2-1~2-5之比較鹼性顯影性感光性樹脂組合物No.1~No.5,因靈敏度低故而不得不提高曝光量,且析像度下降,又,密著性有些亦不理想。
分別於實施例3-1~3-7中所得之鹼性顯影性感光性樹脂組合物No.1~No.7以及比較例2-1~2-5中所得之比較鹼性顯影性感光性樹脂組合物No.1~No.5 44 g中,添加三羥甲基丙烷三丙烯酸酯8.0 g、作為光聚合起始劑(F)之2,4,6-三甲基苯甲醯基二苯基氧化膦1.8 g、作為色料(G)之MA100(碳黑,三菱化學公司製造)3.2 g及PGMAc 75 g,充分攪拌,獲得著色鹼性顯影性感光性樹脂組合物No.1~No.7以及比較著色鹼性顯影性感光性樹脂組合物No.1~No.5。
以與上述實施例3-1~3-7相同之方式,對上述實施例4-1~4-7中製備之著色鹼性顯影性感光性樹脂組合物No.1~No.7、以及比較例3-1~3-5中製備之比較鹼性顯影性感光性樹脂組合物No.1~No.5進行評價。結果示於[表3]。
實施例4-1~4-7之著色鹼性顯影性感光性樹脂組合物No.1~No.7係高靈敏度且析像度、密著性優異者。
相對於此,比較例3-1~3-5之比較著色鹼性顯影性感光性樹脂組合物No.1~No.5,因靈敏度低故而不得不提高曝光量,且析像度下降,又,密著性有些亦不理想。
本發明之環氧化合物(A),可用作鹼性顯影性樹脂組合物及鹼性顯影性感光性樹脂組合物之原料,以該環氧化合物(A)為原料而獲得之鹼性顯影性樹脂組合物及鹼性顯影
性感光性樹脂組合物的靈敏度、析像度、密著性優異。又,本發明之環氧化合物(A)可藉由與硬化劑混合而形成熱硬化性之環氧樹脂組合物。
Claims (7)
- 一種環氧加成化合物,其具有於以下述通式(I)所表示之環氧化合物上加成不飽和一元酸之結構:
- 一種環氧樹脂組合物,其包含以下述通式(I)所表示之環氧化合物及硬化劑:[化1]
- 一種鹼性顯影性樹脂組合物,其特徵在於:含有光聚合性不飽和化合物,該化合物具有由如請求項1之環氧加成化合物與多元酸酐之酯化反應所獲得的反應產物之結構。
- 一種鹼性顯影性樹脂組合物,其特徵在於:含有光聚合性不飽和化合物,該化合物具有於如請求項3之光聚合性不飽和化合物上進一步加成環氧化合物而獲得的反應產物之結構。
- 一種鹼性顯影性樹脂組合物,其特徵在於:含有光聚合 性不飽和化合物,該化合物具有使如請求項4之光聚合性不飽和化合物進一步與多元酸酐進行酯化反應而獲得的反應產物之結構。
- 一種鹼性顯影性感光性樹脂組合物,其特徵在於:使如請求項3至5中任一項之鹼性顯影性樹脂組合物中含有光聚合起始劑。
- 一種著色鹼性顯影性感光性樹脂組合物,其特徵在於:使如請求項6之鹼性顯影性感光性樹脂組合物中進一步含有色料。
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JPWO2008139924A1 (ja) | 2010-08-05 |
TWI620741B (zh) | 2018-04-11 |
TW201402558A (zh) | 2014-01-16 |
JP5214598B2 (ja) | 2013-06-19 |
ATE526321T1 (de) | 2011-10-15 |
CN101622236A (zh) | 2010-01-06 |
KR20100014836A (ko) | 2010-02-11 |
WO2008139924A1 (ja) | 2008-11-20 |
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