TWI776586B - 聚苯并噁唑前驅物及其應用 - Google Patents
聚苯并噁唑前驅物及其應用 Download PDFInfo
- Publication number
- TWI776586B TWI776586B TW110125312A TW110125312A TWI776586B TW I776586 B TWI776586 B TW I776586B TW 110125312 A TW110125312 A TW 110125312A TW 110125312 A TW110125312 A TW 110125312A TW I776586 B TWI776586 B TW I776586B
- Authority
- TW
- Taiwan
- Prior art keywords
- acid
- mol
- dicarboxylic acid
- polybenzoxazole precursor
- resin composition
- Prior art date
Links
- 229920002577 polybenzoxazole Polymers 0.000 title claims abstract description 37
- 239000002243 precursor Substances 0.000 title claims abstract description 36
- 239000011342 resin composition Substances 0.000 claims abstract description 43
- -1 dicarboxylic acid compound Chemical class 0.000 claims description 76
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 31
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 238000011161 development Methods 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 239000011229 interlayer Substances 0.000 claims description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 6
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 6
- 239000002798 polar solvent Substances 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000005248 alkyl aryloxy group Chemical group 0.000 claims description 4
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 claims description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 3
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 claims description 3
- GBURUDXSBYGPBL-UHFFFAOYSA-N 2,2,3-trimethylhexanedioic acid Chemical compound OC(=O)C(C)(C)C(C)CCC(O)=O GBURUDXSBYGPBL-UHFFFAOYSA-N 0.000 claims description 3
- BTUDGPVTCYNYLK-UHFFFAOYSA-N 2,2-dimethylglutaric acid Chemical compound OC(=O)C(C)(C)CCC(O)=O BTUDGPVTCYNYLK-UHFFFAOYSA-N 0.000 claims description 3
- KJXMXCRSMLOXBM-UHFFFAOYSA-N 2,3-diethylbutanedioic acid Chemical compound CCC(C(O)=O)C(CC)C(O)=O KJXMXCRSMLOXBM-UHFFFAOYSA-N 0.000 claims description 3
- JZUMVFMLJGSMRF-UHFFFAOYSA-N 2-Methyladipic acid Chemical compound OC(=O)C(C)CCCC(O)=O JZUMVFMLJGSMRF-UHFFFAOYSA-N 0.000 claims description 3
- LFEWXDOYPCWFHR-UHFFFAOYSA-N 4-(4-carboxybenzoyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C=C1 LFEWXDOYPCWFHR-UHFFFAOYSA-N 0.000 claims description 3
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 claims description 3
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- CGBYBGVMDAPUIH-UHFFFAOYSA-N acide dimethylmaleique Natural products OC(=O)C(C)=C(C)C(O)=O CGBYBGVMDAPUIH-UHFFFAOYSA-N 0.000 claims description 3
- 239000001361 adipic acid Substances 0.000 claims description 3
- 235000011037 adipic acid Nutrition 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- LNGJOYPCXLOTKL-UHFFFAOYSA-N cyclopentane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)C1 LNGJOYPCXLOTKL-UHFFFAOYSA-N 0.000 claims description 3
- CGBYBGVMDAPUIH-ARJAWSKDSA-N dimethylmaleic acid Chemical compound OC(=O)C(/C)=C(/C)C(O)=O CGBYBGVMDAPUIH-ARJAWSKDSA-N 0.000 claims description 3
- OREAFAJWWJHCOT-UHFFFAOYSA-N dimethylmalonic acid Chemical compound OC(=O)C(C)(C)C(O)=O OREAFAJWWJHCOT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 claims description 3
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims description 3
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 239000004065 semiconductor Substances 0.000 claims description 3
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 2
- LWBHHRRTOZQPDM-UHFFFAOYSA-N undecanedioic acid Chemical compound OC(=O)CCCCCCCCCC(O)=O LWBHHRRTOZQPDM-UHFFFAOYSA-N 0.000 claims 2
- 229920000265 Polyparaphenylene Polymers 0.000 claims 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 1
- 150000002916 oxazoles Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 96
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- 230000015572 biosynthetic process Effects 0.000 description 37
- 238000003786 synthesis reaction Methods 0.000 description 37
- 125000006239 protecting group Chemical group 0.000 description 34
- 239000012265 solid product Substances 0.000 description 25
- 239000008367 deionised water Substances 0.000 description 24
- 229910021641 deionized water Inorganic materials 0.000 description 24
- 239000002904 solvent Substances 0.000 description 18
- 238000004090 dissolution Methods 0.000 description 17
- 239000012299 nitrogen atmosphere Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 16
- 239000003517 fume Substances 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 230000018109 developmental process Effects 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- PGYJSURPYAAOMM-UHFFFAOYSA-N 2-ethenoxy-2-methylpropane Chemical compound CC(C)(C)OC=C PGYJSURPYAAOMM-UHFFFAOYSA-N 0.000 description 8
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 150000001263 acyl chlorides Chemical class 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-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
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- WEQHQGJDZLDFID-UHFFFAOYSA-J thorium(iv) chloride Chemical compound Cl[Th](Cl)(Cl)Cl WEQHQGJDZLDFID-UHFFFAOYSA-J 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- UIAFKZKHHVMJGS-UHFFFAOYSA-N 2,4-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 2
- FEPBITJSIHRMRT-UHFFFAOYSA-N 4-hydroxybenzenesulfonic acid Chemical compound OC1=CC=C(S(O)(=O)=O)C=C1 FEPBITJSIHRMRT-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 101000738322 Homo sapiens Prothymosin alpha Proteins 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 102100037925 Prothymosin alpha Human genes 0.000 description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- XOIYZMDJFLKIEI-UHFFFAOYSA-N (hydroxysulfonimidoyl)oxybenzene Chemical compound NS(=O)(=O)OC1=CC=CC=C1 XOIYZMDJFLKIEI-UHFFFAOYSA-N 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-M 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
- CBGBMDNBHHELTJ-UHFFFAOYSA-N 1,2-dimethylperylene Chemical group C1=CC(C2=C(C(C)=CC=3C2=C2C=CC=3)C)=C3C2=CC=CC3=C1 CBGBMDNBHHELTJ-UHFFFAOYSA-N 0.000 description 1
- SJJCQDRGABAVBB-UHFFFAOYSA-N 1-hydroxy-2-naphthoic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CC=C21 SJJCQDRGABAVBB-UHFFFAOYSA-N 0.000 description 1
- GDBITPXOESTAML-UHFFFAOYSA-N 2-(4-hydroxyphenyl)-3-methylbutyric acid Chemical compound CC(C)C(C(O)=O)C1=CC=C(O)C=C1 GDBITPXOESTAML-UHFFFAOYSA-N 0.000 description 1
- DNUYOWCKBJFOGS-UHFFFAOYSA-N 2-[[10-(2,2-dicarboxyethyl)anthracen-9-yl]methyl]propanedioic acid Chemical compound C1=CC=C2C(CC(C(=O)O)C(O)=O)=C(C=CC=C3)C3=C(CC(C(O)=O)C(O)=O)C2=C1 DNUYOWCKBJFOGS-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- IGUMWDXKAUEIDE-UHFFFAOYSA-N 2-chloro-1,3,4-trifluoro-5-methylbenzene Chemical compound CC1=CC(F)=C(Cl)C(F)=C1F IGUMWDXKAUEIDE-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- XFDUHJPVQKIXHO-UHFFFAOYSA-N 3-aminobenzoic acid Chemical compound NC1=CC=CC(C(O)=O)=C1 XFDUHJPVQKIXHO-UHFFFAOYSA-N 0.000 description 1
- YZBCICVNBHNLTK-UHFFFAOYSA-N 4,5-dihydroxyphthalic acid Chemical compound OC(=O)C1=CC(O)=C(O)C=C1C(O)=O YZBCICVNBHNLTK-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- AEKVBBNGWBBYLL-UHFFFAOYSA-N 4-fluorobenzonitrile Chemical compound FC1=CC=C(C#N)C=C1 AEKVBBNGWBBYLL-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- HETHVZIPWDNMBD-UHFFFAOYSA-N NS(OC(C1=CC=CC=C1)C1=CC=CC=C1)(=O)=O Chemical compound NS(OC(C1=CC=CC=C1)C1=CC=CC=C1)(=O)=O HETHVZIPWDNMBD-UHFFFAOYSA-N 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- DQTRUCSKJZOPCX-UHFFFAOYSA-N aniline;formic acid Chemical compound [O-]C=O.[NH3+]C1=CC=CC=C1 DQTRUCSKJZOPCX-UHFFFAOYSA-N 0.000 description 1
- 239000003006 anti-agglomeration agent Substances 0.000 description 1
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229940114055 beta-resorcylic acid Drugs 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000005520 diaryliodonium group Chemical group 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- BDUPRNVPXOHWIL-UHFFFAOYSA-N dimethyl sulfite Chemical compound COS(=O)OC BDUPRNVPXOHWIL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CNEKKZXYBHKSDC-UHFFFAOYSA-N ethyl acetate;propane-1,2-diol Chemical compound CC(O)CO.CCOC(C)=O CNEKKZXYBHKSDC-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001459 lithography Methods 0.000 description 1
- IJFXRHURBJZNAO-UHFFFAOYSA-N meta--hydroxybenzoic acid Natural products OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005146 naphthylsulfonyl group Chemical group C1(=CC=CC2=CC=CC=C12)S(=O)(=O)* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- GSWAOPJLTADLTN-UHFFFAOYSA-N oxidanimine Chemical compound [O-][NH3+] GSWAOPJLTADLTN-UHFFFAOYSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- KBZVFSSKGBFEBT-UHFFFAOYSA-N propan-2-yloxycyclohexane Chemical compound CC(C)OC1CCCCC1 KBZVFSSKGBFEBT-UHFFFAOYSA-N 0.000 description 1
- ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 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
- 238000005406 washing 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/40—Polyamides containing oxygen in the form of ether groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/42—Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/22—Polybenzoxazoles
-
- 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
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
-
- 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
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
- H01L21/02118—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
- H01L21/02205—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates the layer being characterised by the precursor material for deposition
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/02104—Forming layers
- H01L21/02107—Forming insulating materials on a substrate
- H01L21/02225—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer
- H01L21/0226—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process
- H01L21/02282—Forming insulating materials on a substrate characterised by the process for the formation of the insulating layer formation by a deposition process liquid deposition, e.g. spin-coating, sol-gel techniques, spray coating
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/52—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames
- H01L23/522—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames including external interconnections consisting of a multilayer structure of conductive and insulating layers inseparably formed on the semiconductor body
- H01L23/532—Arrangements for conducting electric current within the device in operation from one component to another, i.e. interconnections, e.g. wires, lead frames including external interconnections consisting of a multilayer structure of conductive and insulating layers inseparably formed on the semiconductor body characterised by the materials
- H01L23/5329—Insulating materials
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Power Engineering (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Computer Hardware Design (AREA)
- Manufacturing & Machinery (AREA)
- General Chemical & Material Sciences (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Description
本發明係關於一種聚苯并噁唑前驅物,特別係關於一種可用於形成具高頻特性之膜的聚苯并噁唑前驅物。
5G高頻通訊技術須包括高頻傳輸、廣連結以及低延遲等特點,發展一種具有低介電損耗材料並應用於高頻訊號傳輸是一個重要的課題,其中材料的介電常數(Dielectric constant, Dk)與介電損失因子(Dissipation factor, Df)是影響傳輸速度與訊號品質的重要因素。另一方面,於半導體元件中,主要朝向將晶片或晶圓封裝材料作微細化製程,常使用的方式是利用感光性樹脂作微影製程來達到所需細線路圖案的需求。
感光樹脂組成物一般分為正型及負型的感光樹脂組成物,在圖案硬化膜的微細化製程上,正型感光樹脂組成物具有高感度以及高解析度等優勢。然而,除了考慮到圖案的解析度外,同時也要一併考慮到未曝光區與曝光區高溶解對比性的要求。傳統上,使用萘醌二疊氮化合物與鹼可溶樹脂組合的正型感光樹脂組成物,雖可降低未曝光區的溶解速率,但提高萘醌二疊氮化合物比例,反而造成曝光區在相同的感光波長下透過率變低,顯影時間過長,引起解析度降低,以及溶解對比性下降問題。此外,萘醌二疊氮化合物本身的極性分子結構,會使得正型感光性樹脂組成物所形成的圖案硬化膜具有較差的介電損耗特性。
有鑒於上述技術問題,本發明目的即係提供一種可用於形成具高頻特性及高對比性之膜的樹脂組成物。
為達上述目的,本發明係提供一種聚苯并噁唑前驅物,其包含式(I)所示之結構:
其中,
Y各自獨立為二價基團;
Z各自獨立為二羧酸化合物之二價殘基;
R
1各自獨立為氫或式(II)所示之基團:
(II),
其中,於R
1中該式(II)所示之基團所占的量為25~65莫耳%,且R
a、R
b及R
c各自獨立為氫、烷基、脂環基、芳基、雜脂環基、雜芳基、雜芳基烷基或芳基烷基;或者R
b、和R
b鍵結之碳原子、R
c、與和R
c鍵結之氧原子合在一起形成含氧之雜脂環;
i為20~100莫耳%,j為0~80莫耳%,且i及j之總和為100莫耳%;及
V各自獨立為式(III)所示之基團:
(III),
其中,A各自獨立為-CH
2-、-C(CH
3)
2-、-O-、-S-、-(S=O)-、-S(O)
2-或-C(CF
3)
2-;R各自獨立為氫、烷基、氟烷基、烷氧基、氟烷氧基、矽氧烷基(siloxane group)、環烷基、環烷氧基、烷基環烷氧基、氟烷基環烷氧基、環烷基磺醯基、烷基環烷基磺醯基、氟烷基環烷基磺醯基、芳基、芳氧基、烷基芳氧基、氟烷基芳氧基、芳基磺醯基、烷基芳基磺醯基或氟烷基芳基磺醯基;且n為0或2。
較佳地,Y係選自-CH
2-、-C(CH
3)
2-、-O-、-S-、-(S=O)-、-S(O)
2-或-C(CF
3)
2-。
較佳地,該二羧酸化合物係選自脂肪族二羧酸化合物或芳香族二羧酸化合物。
更佳地,該脂肪族二羧酸化合物係選自丙二酸、二甲基丙二酸、馬來酸、二甲基馬來酸、琥珀酸、戊二酸、2,2-二甲基戊二酸、己二酸、2,3-二乙基琥珀酸、2-甲基己二酸、三甲基己二酸、庚二酸、辛二酸、壬二酸、癸二酸、十一碳二酸、十二碳二酸、1,4-環己烷二甲酸或1,3-環戊烷二羧酸。
更佳地,該芳香族二羧酸化合物係選自對苯二甲酸、間苯二甲酸、2,6-萘二羧酸、2,7-萘二羧酸、1,4-萘二羧酸、4,4'-二苯醚二甲酸、二苯甲酮-4,4'-二羧酸、二苯碸-4,4 '-二羧酸或4,4' -聯苯二甲酸。
本發明亦提供一種樹脂組成物,其包含:一聚合物,其包含前述聚苯并噁唑前驅物及前述聚苯并噁唑前驅物經環化所得之聚苯并噁唑中之至少一者;一光酸產生劑;及非質子型極性溶劑。
較佳地,該樹脂組成物進一步包含一熱酸產生劑。
較佳地,該樹脂組成物所形成之膜於10 GHz下之介電損失因子係小於0.01。
較佳地,該樹脂組成物所形成之膜之解析尺寸係小於10μm。
較佳地,該樹脂組成物所形成之膜於顯影前後依據下式計算所得之未曝光區膜厚損失率小於25%:
未曝光區膜厚損失率(%)=(顯影前的膜厚-顯影後的膜厚)/顯影前的膜厚。
本發明再提供一種層間絕緣膜,其係將前述樹脂組成物予以硬化而得之硬化膜。
本發明又提供一種半導體裝置,其包含上述之層間絕緣膜。
本發明藉由將新穎之二羧酸導入於聚苯并噁唑前驅物中,而使該聚苯并噁唑前驅物因該二羧酸之側鏈結構及分子鏈長,而於鹼性顯影液(例如:2.38%四甲基氫氧化銨)中的溶解速率大幅下降。除此之外,本發明亦藉由將特定之保護基導入於聚苯并噁唑前驅物中,以保護前驅物中之酚性羥基,而使聚苯并噁唑前驅物不溶解於鹼性水溶液,如此,當該聚苯并噁唑前驅物與光酸產生劑配搭時,其所形成之樹脂組成物經由曝光顯影製程後,即可產生化學增幅效果,從而提高整體的溶解對比性。此外,因本發明所選用的保護基團極性較低,亦可維持聚苯并噁唑前驅物具有低介電損耗特性。
於本發明中,「*」係指示連接點(linking point)。
於本發明中,「二羧酸化合物之二價殘基」係指二羧酸化合物移除二個之羧基(-COOH)後所殘留之二價基團。茲舉例說明如下:
二羧酸化合物 | 二羧酸化合物之二價殘基 |
癸二酸 (Decanedioic acid): | |
4,4-二苯醚二甲酸: |
本發明所提供之樹脂組成物係包含:一聚合物,其係包含一聚苯并噁唑前驅物及該聚苯并噁唑前驅物經環化所得之聚苯并噁唑中之至少一者;一光酸產生劑;及非質子型極性溶劑。
於式(I)中,Y每次出現時可為相同或不同,可為二價基團。較佳地,Y係選自-CH
2-、-C(CH
3)
2-、-O-、-S-、-(S=O)- 、-S(O)
2-或-C(CF
3)
2-。
於式(I)中,Z每次出現時可為相同或不同,可為二羧酸化合物之二價殘基。較佳地,該二羧酸化合物係選自脂肪族二羧酸化合物或芳香族二羧酸化合物。該脂肪族二羧酸化合物之實例包含但不限於:丙二酸、二甲基丙二酸、馬來酸、二甲基馬來酸、琥珀酸、戊二酸、2,2-二甲基戊二酸、己二酸、2,3-二乙基琥珀酸、2-甲基己二酸、三甲基己二酸、庚二酸、辛二酸、壬二酸、癸二酸、十一碳二酸、十二碳二酸、1,4-環己烷二甲酸、1,3-環戊烷二羧酸。該芳香族二羧酸化合物之實例包含但不限於:對苯二甲酸、間苯二甲酸、2,6-萘二羧酸、2,7-萘二羧酸、1,4-萘二羧酸、4,4'-二苯醚二甲酸、二苯甲酮-4,4'-二羧酸、二苯碸-4,4 '-二羧酸、4,4' -聯苯二甲酸。於合成本發明之聚苯并噁唑前驅物時,該些羧酸化合物可單獨使用或組合二種以上(諸如:三種、四種)使用。
於式(I)中,R
1中該式(II)所示之基團所占的量為25~65莫耳%,較佳為35~55莫耳%。R
a、R
b及R
c各自獨立為(亦即,每次出現可為相同或不同)氫、烷基、脂環基、芳基、雜脂環基、雜芳基、雜芳基烷基或芳基烷基;或者R
b、和R
b鍵結之碳原子、R
c、與和R
c鍵結之氧原子合在一起形成含氧之雜脂環。該烷基之實例包含但不限於:甲基、乙基、丙基、丁基(諸如:異丁基、第三丁基)、戊基己基。較佳地,該烷基為甲基、乙基、丙基或丁基。該脂環基之實例包含但不限於:環烷基(諸如:環丁基、環戊基、環己基、環庚基)、環烯基(諸如:環戊烯基、環己烯基)。該芳基之實例包含但不限於:苯基、萘基。該雜脂環基可為5員雜脂環基、6員雜脂環基或7員雜脂環基。該雜脂環基之實例包含但不限於:四氫呋喃基(諸如:2-四氫呋喃基)、四氫吡咯基、四氫吡喃基(諸如:2-四氫吡喃基)。該雜芳基之實例包含但不限於:呋喃基、吡啶基、咪唑基。該雜芳基烷基之實例包含但不限於:呋喃基甲基(諸如:2-呋喃基甲基)、吡啶基甲基。該芳基烷基之實例包含但不限於:苯甲基、苯乙基、苯丙基、苯丁基。該含氧之雜脂環之實例包含但不限於:四氫呋喃基(諸如:2-四氫呋喃基)、四氫吡喃基(諸如:2-呋喃基甲基)。
於本發明中,該式(II)所示之基團主要係扮演保護基之角色。該保護基團與酸作用後會脫離,使受到保護之羥基或羧酸基等基團還原,使曝光區之樹脂可在鹼性溶液下溶解。保護基使用比例因應不同之衍生自二羧酸之結構與保護基特性而有不同的適合配比,考量溶解速率,保護基之比例較佳係介於25~65 mol%,更佳係介於35~55mol%,亦即,於R
1中氫所占的量相對於保護基所占的量較佳係於25~65 mol%,更佳係介於35~55mol%(諸如:38~50mol%、39~50mol%、39~45mol%)。
於式(I)中,i為20~100莫耳%,j為0~80莫耳%,且i及j之總和為100莫耳%。於某些實施態樣中,i為40~100莫耳%,j為0~60莫耳%。於某些實施態樣中,i為60~100莫耳%,j為0~40莫耳%。於某些實施態樣中,i為20~80莫耳%,j為20~80莫耳%。
於式(III)中,A每次出現可為相同或不同,可為-CH
2-、-C(CH
3)
2-、-O-、-S-、-(S=O)-、-S(O)
2-或-C(CF
3)
2-。
於式(III)中,R每次出現可為相同或不同,可為氫、烷基(諸如:甲基、乙基、丙基、丁基)、氟烷基(諸如:CF
3、CF
3-CH
2-、CF
3-CF
3-)、烷氧基(諸如:甲氧基、乙氧基、丙氧基、丁氧基)、氟烷氧基(諸如:CF
3-O-、CF
3-CH
2-O-、CF
3-CF
2-O-)、矽氧烷基(siloxane group)、環烷基(諸如:環丁基、環戊基、環己基)、環烷氧基、烷基環烷氧基、氟烷基環烷氧基、環烷基磺醯基、烷基環烷基磺醯基、氟烷基環烷基磺醯基、芳基(諸如:苯基、萘基)、芳氧基、烷基芳氧基、氟烷基芳氧基、芳基磺醯基、烷基芳基磺醯基或氟烷基芳基磺醯基;且n為0或2。
本發明中用語「環烷氧基」係指-OE基,其中E係指環烷基。環烷氧基之實例包含但不限於:環丁氧基、環戊氧基、環己氧基。
本發明中用語「烷基環烷氧基」係指經烷基取代之環烷氧基。烷基環烷氧基之實例包含但不限於:甲基環丁氧基、甲基環戊氧基、甲基環己氧基、乙基環丁氧基、乙基環戊氧基、乙基環己氧基、丙基環己氧基。
本發明中用語「氟烷基環烷氧基」係指經氟烷基取代之環烷氧基。氟烷基環烷氧基之實例包含但不限於:三氟甲基環丁氧基、三氟甲基環戊氧基、三氟甲基環己氧基。
本發明中用語「環烷基磺醯基」係指-S(O)
2-E,其中E係指環烷基。環烷基磺醯基之實例包含但不限於:環丁基磺醯基、環戊基磺醯基、環己基磺醯基、環庚基磺醯基。
本發明中用語「烷基環烷基磺醯基」係指經烷基取代之環烷基磺醯基。烷基環烷基磺醯基之實例包含但不限於:甲基環丁基磺醯基、甲基環戊基磺醯基、甲基環己基磺醯基、甲基環庚基磺醯基、乙基環己基磺醯基、丙基環己基磺醯基。
本發明中用語「氟烷基環烷基磺醯基」係指經氟烷基取代之環烷基磺醯基。氟烷基環烷基磺醯基之實例包含但不限於:三氟甲基環丁基磺醯基、三氟甲基環戊基磺醯基、三氟甲基環己基磺醯基、三氟甲基環庚基磺醯基、三氟乙基環己基磺醯基、三氟丙基環己基磺醯基。
本發明用語「芳氧基」係指-OAr基,其中Ar係指芳基。芳氧基之實例包含但不限於:苯氧基、萘氧基。
本發明用語「烷基芳氧基」係指經烷基取代之芳氧基。烷基芳氧基之實例包含但不限於:甲基苯氧基、乙基苯氧基、丙基苯氧基、甲基萘氧基。
本發明用語「氟烷基芳氧基」係指經氟烷基取代之芳氧基。氟烷基芳氧基之實例包含但不限於:三氟甲基苯氧基、三氟乙基苯氧基、三氟丙基苯氧基、三氟甲基萘氧基。
本發明用語「芳基磺醯基」係指-S(O)
2-Ar,其中Ar係指芳基。芳基磺醯基之實例包含但不限於:苯磺醯基、萘磺醯基。
本發明用語「烷基芳基磺醯基」係指經烷基取代之芳基磺醯基。烷基芳基磺醯基之實例包含但不限於:甲基苯磺醯基、乙基苯磺醯基、丙基苯磺醯基、甲基萘磺醯基。
本發明用語「氟烷基芳基磺醯基」係指經氟烷基取代之芳基磺醯基。氟烷基芳基磺醯基之實例包含但不限於:三氟甲基苯磺醯基、三氟乙基苯磺醯基、三氟丙基苯磺醯基、三氟甲基萘磺醯基。
於較佳實施態樣中,該式(III)所示之基團係選自:
、
、
、
、
、
、
或
,其中R
3a各自獨立為(即R
3a每次出現時可為相同或不同)氫、烷基或氟烷基。該烷基之實例包含但不限於:甲基、乙基、丙基、丁基、戊基、己基。該氟烷基之實例包含但不限於:三氟甲基、三氟乙基、三氟丙基。
本發明之聚苯并噁唑前驅物可以下述方法製備而得:將二羧酸單體進行醯氯化,接著將所得之二氯醯化合物與雙(鄰-胺基苯酚)化合物於有機溶劑中,進行低溫聚縮合反應,以得聚羥基醯胺。接著,將該聚羥基醯胺與用以生成保護基之化合物(例如:叔丁基乙烯醚、乙基乙烯醚、環己基異丙醚)溶解於有機溶劑中進行反應,並在攪拌下將所得溶液置於受控之溫度條件下直到保護完成(即反應完成),以得具保護基之聚羥基醯胺(即受保護之聚羥基醯胺)。
本發明之聚苯并噁唑前驅物可經環化而形成聚苯并噁唑。具體而言,該聚苯并噁唑前驅物可藉由熱閉環法或化學閉環法而轉化成聚苯并噁唑。該聚苯并噁唑前驅物經環化而形成聚苯并噁唑之方法可藉由習知方法來完成,於此茲不贅述。本發明之聚苯并噁唑可以用一步驟(one-step)或兩步驟(two-step)方法來合成。
該光酸產生劑可使用一般常見之市售產品,主要的紫外吸收波長係介於350奈米至450奈米之間。適合的光酸產生劑可為鎓鹽或鋶鹽等,實例包含但不限於:芳基重氮鎓鹽、二芳基碘鎓鹽(諸如:二苯基碘鎓鹽)、二(烷基芳基)碘鎓鹽(諸如:二(第三丁基苯基)碘鎓鹽)、三烷基鋶鹽(諸如:三甲基鋶鹽)、二烷基單芳基鋶鹽(諸如:二甲基苯基鋶鹽)、二芳基單烷基鋶鹽(諸如:二苯基甲基鋶鹽)、及三芳基鋶鹽。該光酸產生劑較佳係5-丙基磺醯氧基亞氨基-5H-噻吩基-2-亞烷基-2-甲基苯基-乙腈、雙(對-甲苯磺醯基)重氮甲烷、雙(1,1—二甲基已機黃醯基) 重氮甲烷、2-重氮-2-(對-甲苯磺醯基)醋酸環己酯或2-重氮-2-苯磺醯基醋酸三級丁酯。該些光酸產生劑可以單獨使用或組合二種以上(諸如:三種、四種)來使用。以該樹脂組成物之總重計,該光酸產生劑之含量較佳為1~30重量百分比,更佳為5~20重量百分比。
於一較佳實施態樣中,本發明之樹脂組成物進一步包含一熱酸產生劑。熱酸產生劑為酸類化合物,可進一步衍生為酯或鹽類化合物。該熱酸產生劑之實例包含但不限於:對-甲苯磺酸、對-甲苯磺酸甲酯、吡啶-對-甲苯磺酸酯、間-羥基苯甲酸、對-羥基苯甲酸、鄰-羥基苯甲酸、2,4-二羥基苯甲酸、對-羥基苄基甲酸、3-(4-羥基苯基)丙酸、對-羥基苯磺酸、對-羥基苯磺酸酯、對-氨基苯甲酸、間-氨基苯甲酸、間 - 甲苯甲酸、1-羥基-2-萘甲酸、2-(4-羥基苯基)-3-甲基丁酸、2-羥基乙酸、4-羥基間苯二甲酸、4-羥基肉桂酸、3-(4-羥基苯基)丙酸 、4,5-二羥基鄰苯二甲酸,三氟甲磺酸鹽、三氟化硼醚絡合物、六氟磷酸鹽、全氟丁烷磺酸鹽。該些熱酸產生劑可以單獨使用或組合二種以上來使用。以該樹脂組成物之總重計,該熱酸產生劑之含量較佳為0~10重量百分比,更佳為0~5重量百分比,諸如:1~5重量百分比。
該非質子型極性溶劑可使用一般常見之市售溶劑,可選自乙二醇單烷基醚類、乙二醇雙烷基醚類、乙二醇單烷基醋酸酯類、丙二醇單烷基醚類、丙二醇雙烷基醚、丙二醇單烷基醋酸酯類、丙二醇雙烷基醋酸酯類。該非質子型極性溶劑之實例包含:乙二醇丁醚、乙二醇二甲基醚、乙二醇乙酸乙酯、丙二醇甲基醚、丙二醇二甲基醚、丙二醇乙酸乙酯、丙二醇二甲基乙酯、γ–內丁酯、N-甲基吡咯烷酮,但不限於此。該些非質子型極性溶劑可以單獨使用或組合二種以上(諸如:三種、四種)來使用。
於不影響本發明之效果之情況下,該樹脂組成物可視其應用需求進一步包含一添加劑。該添加劑可為高級脂肪酸衍生物、界面活性劑、無機粒子、硬化劑、硬化觸媒、填充劑、抗氧化劑、紫外線吸收劑、抗凝聚劑、流平劑或兩種以上(諸如:三種、四種)上述添加劑之組合。該添加劑之含量較佳係設為該樹脂組成物之固體成分的10質量%以下,諸如:2~8質量%。於某些實施態樣中,該樹脂組成物係不包含該添加劑。
於一較佳實施態樣中,該樹脂組成物為正型感光性樹脂組成物。
於一較佳實施態樣中,該樹脂組成物所形成之膜於10 GHz下之介電損失因子係小於0.01(諸如:小於0.007、小於0.006、小於0.005、小於0.0045)。於一較佳實施態樣中,該樹脂組成物所形成之膜之解析尺寸係小於10μm。
本發明之樹脂組成物係可製成硬化膜而作為層間絕緣膜。該硬化膜之製造方法可包含以下步驟:將該樹脂組成物塗佈於一基板(其可為表面經清潔者)上,以得一經塗佈之基板;對該經塗佈之基板於80~120℃(較佳為90~120℃,諸如:95℃、100℃、105℃、110℃、115℃)進行表面乾燥(此為預烤步驟),進行1~5分鐘,以得一經表面乾燥之基板;對該經表面乾燥之基板於光罩下進行曝光,以得一經曝光之基板;對該經曝光之基板於80~120℃(較佳為90~120℃,諸如:95℃、100℃、105℃、110℃、115℃)進行曝後烤,以形成厚度為10μm之膜;將該膜於室溫下浸泡於作為顯影液之鹼性水溶液(諸如:2.38%之四甲基氫氧化銨(TMAH)),歷時30~90秒,以移除不要之部分而形成具圖案之膜;對該具圖案之膜進行後烤(postbake)處理,以得一硬化膜。
該曝光所使用之光線較佳係紫外線(諸如:g線、h線、i線),且該曝光所使用之曝光量較佳係100~500 mJ/cm
2。該紫外線之照射裝置可為高壓水銀燈、超高壓水銀燈或金屬鹵素燈。該後烤處理可藉由加熱裝置(諸如:熱板或烘箱)進行。該後烤處理的溫度較佳係200~250°C。
因此,本發明亦提供一種層間絕緣膜,其係將前述樹脂組成物予以硬化而得之硬化膜。
以下以實施例進一步說明本發明,但其並非用於限制本發明的範圍,任何熟悉本發明技術領域者,在不違背本發明之精神下所為之改變及修飾,均屬本發明之範圍。
合成例
1
二羧酸
1
之合成:
於抽風櫃內架設500 mL三頸反應瓶,將作為溶劑之二甲基亞碸、氫氧化鉀(0.31mol)、3,5-二甲基苯酚(0.3mol)、對氯三氟甲苯(0.32mol)添加至該反應瓶,並將所得之混合物於氮氣環境下升溫至145℃反應3小時。反應完成後,利用減壓蒸餾去除二甲基亞碸,即可得到二羧酸1之前驅物。
於抽風櫃內架設1000 mL三頸反應瓶,將作為溶劑之水、前述之二羧酸1之前驅物(1.5mol)添加至該反應瓶,並將所得之混合物於氮氣環境下升溫至95℃後,加入1.2 mol之過錳酸鉀。添加完畢後,維持於95℃下反應2小時。之後降溫至70℃,加入乙醇(20 mL)持續攪拌1小時,接著,去除未反應的過錳酸鉀。將所得之溶液以減壓蒸餾去除水,接著加入過量鹽酸後,溶液析出白色固體產物。以去離子水清洗該固體產物,直至洗液為酸鹼值中性後,再利用乙醇/水進行再結晶純化。將所得之結晶粉末置於真空烘箱中,在120℃下烘乾24小時,即獲得純化後之二羧酸1。
1H-NMR(500 MHz, DMSO-d
6, δ ppm)7.26 ppm (2H, d, aromatic), 7.76 ppm (2H, d, aromatic), 7.80 ppm (2H, d, aromatic), 8.28 ppm (1H, s, aromatic)。
二羧酸 1
聚羥基醯胺
1
合成:
於抽風櫃內架設50 mL三頸反應瓶,於氮氣環境下,依序將作為溶劑之甲基吡咯烷酮、二羧酸1(0.0021 mol)及癸二酸(0.0009mol)添加至該反應瓶,待完全溶解後,以冰浴控制反應溫度在0℃至4℃間,緩慢加入氯化亞碸(0.0075 mol),待完全加入後,移除冰浴使反應溫度回復至常溫,再反應1小時,即得到醯氯化產物。
於機械攪拌器上架設100 mL三頸反應瓶,於氮氣環境下,依序將作為溶劑之甲基吡咯烷酮及2,2-雙(3-氨基-4-羥基苯基)-六氟丙烷(0.003 mol)添加至該反應瓶,待完全溶解後,以冰浴控制反應溫度在0℃至4℃間,緩慢加入氧化丙烯(0.006 mol),待完全加入後,將前述醯氯化產物緩慢倒入反應瓶中,維持反應溫度在0℃至4℃間,持續攪拌1小時,接著,移除冰浴,於常溫下反應24小時。
反應24小時後,將反應溶液直接倒入去離子水中,以使固體產物析出,以去離子水反覆清洗5次,再以50%甲醇水溶液清洗一次。將所得之固體產物置入烘箱,於80℃下乾燥24小時,即可獲得聚羥基醯胺1。
具保護基之聚羥基醯胺 1 合成 (A-1-T*):
於抽風櫃內架設100 mL三頸反應瓶,於氮氣環境下,依序將作為溶劑之二甘醇二甲醚及前述之聚羥基醯胺1(0.003 mol)添加至反應瓶,待完全溶解後,加入叔丁基乙烯醚(0.0024 mol),持續攪拌10分鐘。接著,以冰浴控制反應溫度在0℃至4℃間,緩慢加入對甲苯磺酸(0.03 g),待完全加入後,移除冰浴,於常溫下反應5小時。完應完成後,將反應溶液直接倒入去離子水中,以使固體產物析出,再以去離子水清洗5次。將所之固體產物置入烘箱,於60℃下乾燥24小時,即可得到具保護基之聚羥基醯胺1(A-1-T*),其中該保護基(R
1)為
,該OR
1取代羥基(-OH)之比例為40 mol%。
合成例二:
二羧酸
2
合成:
於抽風櫃內架設250 mL三頸反應瓶,將二甲基甲醯胺(作為溶劑)、甲苯(作為溶劑)、碳酸鉀(0.176 mol)、鄰苯二酚(0.88 mol)添加至反應瓶,於氮氣環境下升溫至迴流溫度,利用Dean-Stark裝置使甲苯與水共沸蒸出,待甲苯去除後,再加入對-氟苯甲腈(0.176 mol),升溫至150℃反應3小時。反應完成後,直接將溶液倒入去離子水中,析出白色固體產物,再將乾燥後的產物以甲醇再結晶之。將所得之晶體粉末置入烘箱,在60℃下乾燥12小時,即可得到二羧酸2之前驅物。
於抽風櫃內架設500 mL三頸反應瓶,將乙醇及水(1:1)的混合溶液作為溶劑,並將該混合溶液、前述之二羧酸2之前驅物(0.0545 mol)、氫氧化鉀(1.09 mol)添加至該反應瓶,於氮氣環境下升溫至90℃後反應24小時。將反應後之混合溶液過濾後,加入過量鹽酸,使濾液析出白色固體,在80℃下烘乾24小時,以獲得二羧酸2。
1H-NMR(500 MHz, DMSO-d
6, δ ppm)6.91 ppm (4H, d, aromatic), 7.31 ppm (4H, d, aromatic), 7.35 ppm (4H, d, aromatic), 7.90 ppm (4H, d, aromatic)。
二羧酸 2
聚羥基醯胺
2
合成:
於抽風櫃內架設50 mL三頸反應瓶,於氮氣環境下,依序將作為溶劑之甲基吡咯烷酮作為溶劑、二羧酸2(0.0021 mol)及癸二酸(0.0009mol)添加至該反應瓶。待完全溶解後,以冰浴控制反應溫度在0℃至4℃間,緩慢加入氯化亞碸(0.0075 mol),待完全加入後,移除冰浴使反應溫度回復至常溫,再反應1小時,即得到醯氯化產物。
於機械攪拌器上架設100 mL三頸反應瓶,於氮氣環境下,依序將作為溶劑之甲基吡咯烷酮、2,2-雙(3-氨基-4-羥基苯基)-六氟丙烷(0.003 mol)添加至該反應瓶。待完全溶解後,以冰浴控制反應溫度在0℃至4℃間,緩慢加入氧化丙烯(0.006 mol),待完全加入後,將前述醯氯化產物緩慢倒入反應瓶中,維持反應溫度在0℃至4℃間,持續攪拌1小時,接著移除冰浴,於常溫下反應24小時。
反應24小時後,將反應溶液直接倒入去離子水中,以使固體產物析出,以去離子水反覆清洗5次,再以50%甲醇水溶液清洗一次。將所得之固體產物置入烘箱,於80℃下乾燥24小時,即可獲得聚羥基醯胺2。
具保護基之聚羥基醯胺 2 合成 (A-2-T*):
於抽風櫃內架設100 mL三頸反應瓶,於氮氣環境下,依序將作為溶劑之二甘醇二甲醚劑及前述之聚羥基醯胺2(0.003 mol)添加至該反應瓶。待完全溶解後,加入叔丁基乙烯醚(0.0024 mol),持續攪拌10分鐘。接著,以冰浴控制反應溫度在0℃至4℃間,緩慢加入對甲苯磺酸(0.03 g),待完全加入後,移除冰浴,於常溫下反應5小時。反應完成後,將反應溶液直接倒入去離子水中,以使固體產物析出,再以去離子水清洗5次。將所得之固體產物置入烘箱,於60℃下乾燥24小時,即可得到具保護基之聚羥基醯胺2(A-2-T*),其中該保護基(R
1)為
,該OR
1取代羥基之比例為40 mol%。
合成例三:
聚羥基醯胺
3
合成:
將合成例一中的聚羥基醯胺1合成所使用的二羧酸1(0.0021 mol)及癸二酸(0.0009mol)更換為二羧酸1(0.0015 mol)及癸二酸(0.0015mol),除此之外,其它合成步驟相同,即可獲得聚羥基醯胺3。
具保護基之聚羥基醯胺 3 合成 (A-3-T*):
於抽風櫃內架設100 mL三頸反應瓶,於氮氣環境下,依序將作為溶劑之二甘醇二甲醚及前述之聚羥基醯胺3(0.003 mol)添加至該反應瓶。完全溶解後,加入叔丁基乙烯醚(0.0024 mol),持續攪拌10分鐘。接著,以冰浴控制反應溫度在0℃至4℃間,緩慢加入對甲苯磺酸(0.03 g),待完全加入後,移除冰浴,於常溫下反應5小時。反應完成後,將反應溶液直接倒入去離子水中,以使固體產物析出,再以去離子水清洗5次。將所得之固體產物置入烘箱,於60℃下乾燥24小時,即可得到具保護基之聚羥基醯胺3(A-3-T*),其中該保護基(R
1)為
,該OR
1取代羥基之比例為40 mol%。
合成例四:
聚羥基醯胺
4
合成:
將合成例一中的聚羥基醯胺1合成所使用的二羧酸1(0.0021 mol)及癸二酸(0.0009mol)更換為二羧酸1(0.0009 mol)及癸二酸(0.0021mol),除此之外,其它合成步驟相同,即可獲得聚羥基醯胺4。
具保護基之聚羥基醯胺 4 合成 (A-4-T*):
於抽風櫃內架設100 mL三頸反應瓶,於氮氣環境下,依序將作為溶劑之二甘醇二甲醚及前述之聚羥基醯胺4(0.003 mol)添加至該反應瓶。於完全溶解後,加入叔丁基乙烯醚(0.0024 mol),持續攪拌10分鐘。接著,以冰浴控制反應溫度在0℃至4℃間,緩慢加入對甲苯磺酸(0.03 g),待完全加入後,移除冰浴,於常溫下反應5小時。反應完成後,將反應溶液直接倒入去離子水中,以使固體產物析出,再以去離子水清洗5次。將所得之固體產物置入烘箱,於60℃下乾燥24小時,即可得到具保護基之聚羥基醯胺4(A-4-T*),其中該保護基(R
1)為
,該OR
1取代羥基之比例為40 mol%。
合成例五:
聚羥基醯胺
5
合成:
將合成例一中的聚羥基醯胺1合成所使用的二羧酸1(0.0021 mol)及癸二酸(0.0009mol)更換為二羧酸1(0.0021 mol)及4,4-二苯醚二甲酸(0.0009mol),除此之外,其它合成步驟相同,即可獲得聚羥基醯胺5。
具保護基之聚羥基醯胺 5 合成 (A-5-T*):
於抽風櫃內架設100 mL三頸反應瓶,於氮氣環境下,依序將作為溶劑之二甘醇二甲醚及前述之聚羥基醯胺5(0.003 mol)添加至該反應瓶。於完全溶解後,加入叔丁基乙烯醚(0.0024 mol),持續攪拌10分鐘。接著,以冰浴控制反應溫度在0℃至4℃間,緩慢加入對甲苯磺酸(0.03 g),待完全加入後,移除冰浴,於常溫下反應5小時。反應完成後,將反應溶液直接倒入去離子水中,以使固體產物析出,再以去離子水清洗5次。將所得之固體產物置入烘箱,於60℃下乾燥24小時,即可得到具保護基之聚羥基醯胺5(A-5-T*),其中該保護基(R
1)為
,該OR
1取代羥基之比例為40 mol%。
比較例:
合成例六:
聚羥基醯胺
6
合成:
將合成例一中的聚羥基醯胺1合成所使用的二羧酸1(0.0021 mol)及癸二酸(0.0009mol)更換為二羧酸1(0.0003 mol)及癸二酸(0.0027mol),除此之外,其它合成步驟相同。
具保護基之聚羥基醯胺 6 合成 (B-1-T*):
於抽風櫃內架設100 mL三頸反應瓶,於氮氣環境下,依序將作為溶劑之二甘醇二甲醚及前述之聚羥基醯胺6(0.003 mol)添加至反應瓶。於完全溶解後,加入叔丁基乙烯醚(0.0024 mol),持續攪拌10分鐘。接著,以冰浴控制反應溫度在0℃至4℃間,緩慢加入對甲苯磺酸(0.03 g),待完全加入後,移除冰浴,於常溫下反應5小時。反應完成後,將反應溶液直接倒入去離子水中,以使固體產物析出,再以去離子水清洗5次。將所得之固體產物置入烘箱,於60℃下乾燥24小時,即可得到具保護基之聚羥基醯胺6(B-1-T*),其中該保護基(R
1)為
,該OR
1取代羥基之比例為40 mol%。
合成例七
具 DNQ 保護之聚羥基醯胺 7 合成 (B-2-D):
於抽風櫃內架設100 mL三頸反應瓶,於氮氣環境下,依序將作為溶劑之二甘醇二甲醚及前述之聚羥基醯胺6(0.003 mol)添加至該反應瓶。於完全溶解後,加入1,2-萘醌-2-二疊氮-5-磺醯氯(1,2-naphthoquinonediazide-5-sulfonyl chloride, DNQ-5)(0.0012mol),持續攪拌10分鐘,加入三乙胺(0.0015mmol),於常溫下反應5小時。反應完成後,將反應溶液直接倒入去離子水中,以使固體產物析出,再以去離子水清洗5次。將所得之固體產物置入烘箱,於60℃下乾燥24小時,即可得到具DNQ保護之聚羥基醯胺7(B-2-D),該OR
1取代羥基之比例為20 mol%。
合成例八:
聚羥基醯胺
8
合成:
於抽風櫃內架設50 mL三頸反應瓶,於氮氣環境下,依序將甲基吡咯烷酮(作為溶劑)及4,4-二苯醚二甲酸(0.003 mol)添加至該反應瓶。於完全溶解後,以冰浴控制反應溫度在0℃至4℃間,緩慢加入氯化亞碸(0.0075 mol),待完全加入後,移除冰浴使反應溫度回復至常溫,再反應1.5小時,即得到醯氯化產物。
於機械攪拌器上架設100 mL三頸反應瓶,於氮氣環境下,依序將甲基吡咯烷酮(作為溶劑)及2,2-雙(3-氨基-4-羥基苯基)-六氟丙烷(0.003 mol)添加至該反應瓶。於完全溶解後,以冰浴控制反應溫度在0℃至4℃間,緩慢加入氧化丙烯(0.006 mol),待完全加入後,將前述醯氯化產物緩慢倒入反應瓶中,維持反應溫度在0℃至4℃間,持續攪拌1.5 小時,接著,移除冰浴,於常溫下反應24小時。
待反應24小時後,將反應溶液直接倒入去離子水中,以使固體產物析出,以去離子水反覆清洗5次,再以50%甲醇水溶液清洗一次。將所得之固體產物置入烘箱,於80℃下乾燥24小時,即可獲得聚羥基醯胺8。
具保護基之聚羥基醯胺 8 合成( B-3-T* ):
於抽風櫃內架設100 mL三頸反應瓶,於氮氣環境下,依序將二甘醇二甲醚(作為溶劑)及前述之聚羥基醯胺8(0.003 mol)添加至該反應瓶。於完全溶解後,加入叔丁基乙烯醚(0.0024 mol),持續攪拌10分鐘。接著,以冰浴控制反應溫度在0℃至4℃間,緩慢加入對甲苯磺酸(0.03 g),待完全加入後,移除冰浴,於常溫下反應5小時。反應完成後,將反應溶液直接倒入去離子水中,以使固體產物析出,再以去離子水清洗5次。將所得之固體產物置入烘箱,於60℃下乾燥24小時,即可得到具保護基之聚羥基醯胺8(B-3-T*),其中該保護基(R
1)為
,該OR
1取代羥基之比例為40 mol%。
實施例:正型感光性樹脂組成物之製作
依據表1所載之用量,將成分(A)~成分(D)均勻混合,再以5μm過濾頭過濾,再以脫泡機進行脫泡處理,即可得到實施例1~5及比較例1~4之樹脂組成物。
成分(A)代表各合成例中之具保護基之聚羥基醯胺。成分(B)代表光酸產生劑(5-丙基磺醯氧基亞氨基-5H-噻吩基-2-亞烷基-2-甲基苯基-乙腈,PTMA,Hangzhou GYZ Chemical)。成分(C)代表熱酸產生劑(對-甲苯磺酸甲酯,M
pTOL,Sigma-Aldrich)。成分(D)代表γ-內丁酯(GBL)。
將樹脂組成物經塗膜、曝光、顯影製程後,經由250℃後烤製成膜後,再以下列方法進行評價:
介電常數(dielectric constant,Dk)
使用量測儀 (廠牌:Agilent;型號:HP4291),於10GHz的條件下,採用IPC-TM-650-2.5.5.9標準方法進行量測。
介電損失因子(dissipation factor,Df)
使用量測儀 (廠牌:Agilent;型號:HP4291),於10GHz的條件下,採用IPC-TM-650-2.5.5.9標準方法進行量測。
10μm膜厚的解析度包含:解析尺寸及未曝光區膜厚損失率。
曝光顯影後,以圖案線寬與間隔(線距)之最小尺寸作為計算解析尺寸之依據。解析尺寸係以L/S計算而得,其中L係指線寬;S則係指線距。
L/S為10μm以下,為高解析度,將之評估為 ○
L/S為大於10μm,為低解析度,將之評估為 ×
未曝光區膜厚損失率(%)
測定顯影前的未曝光區膜厚,減去顯影後的未曝光區膜厚,除以顯影前的未曝光區膜厚,藉此求出未曝光區膜厚損失率,公式如下:
未曝光區膜厚損失率(%)=(顯影前的膜厚-顯影後的膜厚)/顯影前的膜厚
未曝區光膜厚損失率小於25%,將之評估為○
未曝區光膜厚損失率介於25~50%範圍,將之評估為Δ
未曝區光膜厚損失率大於50%以上,將之評估為×
上述評價結果顯示於表1。
表1
註釋:
1. T*:代表本發明所開發之保護基
2. D:代表市售之DNQ感光保護基
樹脂組成物組成成分 | 實施例1 | 實施例2 | 實施例3 | 實施例4 | 實施例5 | 比較例1 | 比較例2 | 比較例3 | 比較例4 | |
成分(A) | A-1-T* | 12 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
A-2-T* | 0 | 12 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | |
A-3-T* | 0 | 0 | 12 | 0 | 0 | 0 | 0 | 0 | 0 | |
A-4-T* | 0 | 0 | 0 | 12 | 0 | 0 | 0 | 0 | 0 | |
A-5-T* | 0 | 0 | 0 | 0 | 12 | 0 | 0 | 0 | 0 | |
B-1-T* | 0 | 0 | 0 | 0 | 0 | 12 | 0 | 0 | 0 | |
B-2-D | 0 | 0 | 0 | 0 | 0 | 0 | 12 | 0 | 0 | |
B-3-T* | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 12 | 12 | |
成分(B) | PTMA | 1.2 | 1.2 | 1.2 | 1.2 | 1.2 | 1.2 | 1.2 | 1.2 | 3.6 |
成分(C) | M pTOL | 0.12 | 0.12 | 0.12 | 0.12 | 0.12 | 0.12 | 0.12 | 0.12 | 0.12 |
成分(D) | GBL | 86.68 | 86.68 | 86.68 | 86.68 | 86.68 | 86.68 | 86.68 | 86.68 | 84.28 |
介電性質 | Dk | 2.84 | 2.86 | 2.82 | 2.81 | 2.88 | 2.85 | 2.92 | 3.21 | 3.24 |
Df | 0.0041 | 0.0041 | 0.004 | 0.0038 | 0.0065 | 0.0033 | 0.012 | 0.01 | 0.017 | |
10μm膜厚解析度 | 解析尺寸 | ○ | ○ | ○ | ○ | ○ | X | X | ○ | ○ |
未曝光膜損失率 | ○ | ○ | ○ | ○ | ○ | Δ | ○ | X | Δ |
如表1所示,相較於比較例3及4,實施例1、2、5係具較低之未曝光區膜厚損失率。此乃因本發明之聚苯并噁唑前驅物導入新穎的二羧酸而包含式(III)所示之基團,而式(III)所示之基團之側鏈結構及/或分子鏈長係有助於降低未曝光區膜厚損失率。比較例4雖因光酸產生劑之含量提高而使未曝光區膜厚損失率獲得些微改善,但其介電損失因子同樣因光酸產生劑之含量提高而有所提高,仍大於0.01。此外,相較於比較例2~4,實施例1~5係具有小於0.01之介電損失因子。
自實施例1、3、4與比較例1之比較結果可知,樹脂組成物中之聚合物包含二種二羧酸單元(即結構單元i及結構單元j)時,結構單元i於聚合物中之占比由70、50、30、10%減少時,該樹脂組成物所形成之膜之介電損失因子會隨之下降,但未曝光區膜厚損失率則會隨之升高。另外,自比較例2之結果可知,當樹脂組成物中之聚合物為具DNQ保護基之聚羥基醯胺時,該樹脂組成物所形成之膜雖具良好之未曝光區的膜厚損失率,但其解析尺寸(大於10μm)及介電損失因子(大於0.01)均不佳。
自上可知,依據本發明,可獲得一種能夠形成具高頻特性、高解析度、高對比性及低溫熟化特性之膜的樹脂組成物。
以上所述僅是本發明的優選實施方式,並不用於限制本發明,應當指出,對於本技術領域的普通技術人員來說,在不脫離本發明技術原理的前提下,還可以做出若干改進和變型,這些改進和變型也應視為本發明的保護範圍。
無
無
無
Claims (13)
- 一種聚苯并噁唑前驅物,其包含式(I)所示之結構:
- 如請求項1所述之聚苯并噁唑前驅物,其中Y係選自-CH2-、-C(CH3)2-、-O-、-S-、-(S=O)- -S(O)2-或-C(CF3)2-。
- 如請求項1所述之聚苯并噁唑前驅物,其中該二羧酸化合物係選自脂肪族二羧酸化合物或芳香族二羧酸化合物。
- 如請求項3所述之聚苯并噁唑前驅物,其中該脂肪族二羧酸化合物係選自丙二酸、二甲基丙二酸、馬來酸、二甲基馬來酸、琥珀酸、戊二酸、2,2-二甲基戊二酸、己二酸、2,3-二乙基琥珀酸、2-甲基己二酸、三甲基己二酸、庚二酸、辛二酸、壬二酸、癸二酸、十一碳二酸、十二碳二酸、1,4-環己烷二甲酸或1,3-環戊烷二羧酸。
- 如請求項3所述之聚苯并噁唑前驅物,其中該芳香族二羧酸化合物係選自對苯二甲酸、間苯二甲酸、2,6-萘二羧酸、2,7-萘二羧酸、1,4-萘二羧酸、4,4'-二苯醚二甲酸、二苯甲酮-4,4'-二羧酸、二苯碸-4,4'-二羧酸或4,4'-聯苯二甲酸。
- 一種樹脂組成物,其包含:一聚合物,其包含如請求項1所述之聚苯并噁唑前驅物及如請求項1所述之聚苯并噁唑前驅物經環化所得之聚苯并噁唑中之至少一者;一光酸產生劑;及非質子型極性溶劑。
- 如請求項7所述之樹脂組成物,其進一步包含一熱酸產生劑。
- 如請求項7所述之樹脂組成物,其所形成之膜於10GHz下之介電損失因子係小於0.01。
- 如請求項7所述之樹脂組成物,其所形成之膜之解析尺寸係小於10μm。
- 如請求項7所述之樹脂組成物,其所形成之膜於顯影前後依據下式計算所得之未曝光區膜厚損失率小於25%:未曝光區膜厚損失率(%)=(顯影前的膜厚-顯影後的膜厚)/顯影前的膜厚。
- 一種層間絕緣膜,其係將請求項7所述之樹脂組成物予以硬化而得之硬化膜。
- 一種半導體裝置,其包含如請求項12所述之層間絕緣膜。
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
TW110125312A TWI776586B (zh) | 2021-07-09 | 2021-07-09 | 聚苯并噁唑前驅物及其應用 |
US17/857,827 US11976170B2 (en) | 2021-07-09 | 2022-07-05 | Polybenzoxazole precursor and application thereof |
CN202210796902.5A CN115594848B (zh) | 2021-07-09 | 2022-07-06 | 聚苯并噁唑前体及其应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
TW110125312A TWI776586B (zh) | 2021-07-09 | 2021-07-09 | 聚苯并噁唑前驅物及其應用 |
Publications (2)
Publication Number | Publication Date |
---|---|
TWI776586B true TWI776586B (zh) | 2022-09-01 |
TW202302720A TW202302720A (zh) | 2023-01-16 |
Family
ID=84841713
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW110125312A TWI776586B (zh) | 2021-07-09 | 2021-07-09 | 聚苯并噁唑前驅物及其應用 |
Country Status (3)
Country | Link |
---|---|
US (1) | US11976170B2 (zh) |
CN (1) | CN115594848B (zh) |
TW (1) | TWI776586B (zh) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001066781A (ja) * | 1999-07-29 | 2001-03-16 | Korea Res Inst Of Chem Technol | アセタール又はその環状誘導体の側鎖を有するポリアミド及びそれから調製された耐熱性ホトレジスト組成物 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7803510B2 (en) * | 2005-08-17 | 2010-09-28 | Fujifilm Electronic Materials U.S.A., Inc. | Positive photosensitive polybenzoxazole precursor compositions |
KR101438857B1 (ko) * | 2007-03-12 | 2014-09-05 | 히다치 가세이듀퐁 마이쿠로시스데무즈 가부시키가이샤 | 감광성 수지 조성물, 그 수지 조성물을 이용한 패턴 경화막의 제조방법 및 전자부품 |
WO2009099954A1 (en) * | 2008-02-04 | 2009-08-13 | Fujifilm Electronic Materials U.S.A., Inc. | Novel positive photosensitive resin compositions |
JP5169446B2 (ja) * | 2008-04-28 | 2013-03-27 | 日立化成デュポンマイクロシステムズ株式会社 | 感光性樹脂組成物、該樹脂組成物を用いたポリベンゾオキサゾール膜、パターン硬化膜の製造方法及び電子部品 |
KR101023089B1 (ko) * | 2008-09-29 | 2011-03-24 | 제일모직주식회사 | 포지티브형 감광성 수지 조성물 |
KR101247625B1 (ko) * | 2008-12-31 | 2013-03-29 | 제일모직주식회사 | 포지티브형 감광성 수지 조성물 |
JP2011053458A (ja) * | 2009-09-02 | 2011-03-17 | Hitachi Chemical Dupont Microsystems Ltd | 感光性樹脂組成物、該樹脂組成物を用いたパターン硬化膜の製造方法及び電子部品 |
TWI701271B (zh) * | 2015-06-30 | 2020-08-11 | 日商富士軟片股份有限公司 | 感光性樹脂組成物及其製造方法、硬化膜、硬化膜的製造方法及半導體裝置 |
US20210364919A1 (en) * | 2019-01-23 | 2021-11-25 | Microcosm Technology Co., Ltd. | Photosensitive resin composition and application thereof |
-
2021
- 2021-07-09 TW TW110125312A patent/TWI776586B/zh active
-
2022
- 2022-07-05 US US17/857,827 patent/US11976170B2/en active Active
- 2022-07-06 CN CN202210796902.5A patent/CN115594848B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001066781A (ja) * | 1999-07-29 | 2001-03-16 | Korea Res Inst Of Chem Technol | アセタール又はその環状誘導体の側鎖を有するポリアミド及びそれから調製された耐熱性ホトレジスト組成物 |
Also Published As
Publication number | Publication date |
---|---|
CN115594848A (zh) | 2023-01-13 |
TW202302720A (zh) | 2023-01-16 |
CN115594848B (zh) | 2024-07-02 |
US20230041833A1 (en) | 2023-02-09 |
US11976170B2 (en) | 2024-05-07 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5030955B2 (ja) | 新規ポジ型感光性ポリベンゾオキサゾール前躯体組成物 | |
EP1609024B1 (en) | Photosensitive resin compositions | |
TWI471361B (zh) | 新穎的正型光敏樹脂組成物 | |
JP4759613B2 (ja) | 新規な感光性樹脂組成物 | |
JP2008535003A (ja) | 新規な感光性樹脂組成物 | |
KR100913058B1 (ko) | 포지티브형 감광성 수지 조성물, 패턴 형성 방법 및 반도체소자 | |
JP2014191252A (ja) | 感光性樹脂組成物、硬化膜、保護膜、半導体装置および表示体装置 | |
TWI413865B (zh) | 正型光敏樹脂組成物 | |
JP4522412B2 (ja) | 新規な感光性樹脂組成物 | |
KR101186675B1 (ko) | 포지티브형 감광성 조성물 | |
JP4088910B2 (ja) | 新規な感光性樹脂組成物 | |
TWI776586B (zh) | 聚苯并噁唑前驅物及其應用 | |
KR20090088862A (ko) | 포지티브형 감광성 수지 조성물, 경화막, 보호막, 절연막 및 그것을 이용한 반도체 장치, 표시체 장치 | |
KR101200140B1 (ko) | 포지티브형 감광성 조성물 | |
KR20110022661A (ko) | 포지티브형 감광성 수지 조성물, 경화막, 보호막, 절연막 및 그것들을 이용한 반도체 장치, 표시체 장치 | |
CN101566796A (zh) | 低温固化性感光性树脂组合物 | |
JP2981024B2 (ja) | ポジ型感光性樹脂組成物 | |
JP2011053678A (ja) | ポジ型感光性組成物 | |
JP4530949B2 (ja) | 感光性樹脂組成物及びそれを用いた半導体装置の製造方法 | |
KR101333690B1 (ko) | 포지티브형 감광성 수지 조성물 | |
JPH0511451A (ja) | ポジ型感光性樹脂組成物 | |
KR20120110896A (ko) | 신규 폴리아미드 유도체를 포함하는 포지티브형 감광성 수지 조성물 | |
JP2007297531A (ja) | ポリアミド樹脂、該樹脂を用いた感光性樹脂組成物及び半導体装置の製造方法 | |
JP4166058B2 (ja) | ポジ型感光性樹脂組成物及び半導体装置 | |
KR20200038124A (ko) | 감광성 수지 조성물, 이를 이용한 감광성 수지막 및 전자 소자 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
GD4A | Issue of patent certificate for granted invention patent |