JP5988122B1 - ナフトール型カリックスアレーン化合物及びその製造方法、感光性組成物、レジスト材料、並びに塗膜 - Google Patents
ナフトール型カリックスアレーン化合物及びその製造方法、感光性組成物、レジスト材料、並びに塗膜 Download PDFInfo
- Publication number
- JP5988122B1 JP5988122B1 JP2016509801A JP2016509801A JP5988122B1 JP 5988122 B1 JP5988122 B1 JP 5988122B1 JP 2016509801 A JP2016509801 A JP 2016509801A JP 2016509801 A JP2016509801 A JP 2016509801A JP 5988122 B1 JP5988122 B1 JP 5988122B1
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- JP
- Japan
- Prior art keywords
- group
- naphthol
- calixarene compound
- type calixarene
- substituent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- -1 calixarene compound Chemical class 0.000 title claims abstract description 192
- 239000000203 mixture Substances 0.000 title claims abstract description 91
- 238000000576 coating method Methods 0.000 title claims abstract description 46
- 239000011248 coating agent Substances 0.000 title claims abstract description 44
- 239000000463 material Substances 0.000 title claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 14
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 title claims description 57
- 125000001424 substituent group Chemical group 0.000 claims abstract description 46
- 125000003118 aryl group Chemical group 0.000 claims abstract description 37
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 36
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 239000003960 organic solvent Substances 0.000 claims description 28
- 150000001299 aldehydes Chemical class 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000003377 acid catalyst Substances 0.000 claims description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 12
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 6
- 229940093475 2-ethoxyethanol Drugs 0.000 claims description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 2
- 238000005979 thermal decomposition reaction Methods 0.000 abstract description 29
- 239000003513 alkali Substances 0.000 abstract description 27
- 206010034972 Photosensitivity reaction Diseases 0.000 abstract description 22
- 230000036211 photosensitivity Effects 0.000 abstract description 22
- 239000002904 solvent Substances 0.000 abstract description 22
- 239000000126 substance Substances 0.000 abstract description 4
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 239000010408 film Substances 0.000 description 64
- 229920005989 resin Polymers 0.000 description 46
- 239000011347 resin Substances 0.000 description 46
- 150000001875 compounds Chemical class 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 238000011156 evaluation Methods 0.000 description 23
- 125000004432 carbon atom Chemical group C* 0.000 description 17
- 230000000052 comparative effect Effects 0.000 description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 13
- 239000012044 organic layer Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 229920003986 novolac Polymers 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- 230000035945 sensitivity Effects 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 239000003504 photosensitizing agent Substances 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 229920002120 photoresistant polymer Polymers 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical group COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 8
- 229910052710 silicon Inorganic materials 0.000 description 8
- 239000010703 silicon Substances 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 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 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 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 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 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 5
- 239000000945 filler Substances 0.000 description 5
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 4
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical group [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 238000001312 dry etching Methods 0.000 description 4
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- 238000000434 field desorption mass spectrometry Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 150000003460 sulfonic acids Chemical class 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 3
- YGCOKJWKWLYHTG-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]-(hydroxymethyl)amino]methanol Chemical compound OCN(CO)C1=NC(N(CO)CO)=NC(N(CO)CO)=N1 YGCOKJWKWLYHTG-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000003973 paint Substances 0.000 description 3
- 239000005011 phenolic resin Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920003987 resole Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 3
- MWZJGRDWJVHRDV-UHFFFAOYSA-N 1,4-bis(ethenoxy)butane Chemical compound C=COCCCCOC=C MWZJGRDWJVHRDV-UHFFFAOYSA-N 0.000 description 2
- OITQDWKMIPXGFL-UHFFFAOYSA-N 1-hydroxy-2-naphthaldehyde Chemical compound C1=CC=C2C(O)=C(C=O)C=CC2=C1 OITQDWKMIPXGFL-UHFFFAOYSA-N 0.000 description 2
- CPEXFJVZFNYXGU-UHFFFAOYSA-N 2,4,6-trihydroxybenzophenone Chemical compound OC1=CC(O)=CC(O)=C1C(=O)C1=CC=CC=C1 CPEXFJVZFNYXGU-UHFFFAOYSA-N 0.000 description 2
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- GXYCPGOCXLHIAT-UHFFFAOYSA-N 2-cyclohexyl-6-[(3-cyclohexyl-2-hydroxyphenyl)-(2-hydroxyphenyl)methyl]phenol Chemical compound OC1=CC=CC=C1C(C=1C(=C(C2CCCCC2)C=CC=1)O)C1=CC=CC(C2CCCCC2)=C1O GXYCPGOCXLHIAT-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-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
- IBGBGRVKPALMCQ-UHFFFAOYSA-N 3,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1O IBGBGRVKPALMCQ-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- WXYSZTISEJBRHW-UHFFFAOYSA-N 4-[2-[4-[1,1-bis(4-hydroxyphenyl)ethyl]phenyl]propan-2-yl]phenol Chemical compound C=1C=C(C(C)(C=2C=CC(O)=CC=2)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WXYSZTISEJBRHW-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-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
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- XNWPXDGRBWJIES-UHFFFAOYSA-N Maclurin Chemical compound OC1=CC(O)=CC(O)=C1C(=O)C1=CC=C(O)C(O)=C1 XNWPXDGRBWJIES-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- IYFATESGLOUGBX-YVNJGZBMSA-N Sorbitan monopalmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O IYFATESGLOUGBX-YVNJGZBMSA-N 0.000 description 2
- 239000004147 Sorbitan trioleate Substances 0.000 description 2
- PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000012790 adhesive layer Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
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- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005446 heptyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical class I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- YSGBMDFJWFIEDF-UHFFFAOYSA-N methyl 2-hydroxy-3-methylbutanoate Chemical compound COC(=O)C(O)C(C)C YSGBMDFJWFIEDF-UHFFFAOYSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006611 nonyloxy group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001579 optical reflectometry Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- QUBQYFYWUJJAAK-UHFFFAOYSA-N oxymethurea Chemical compound OCNC(=O)NCO QUBQYFYWUJJAAK-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- LSSGAGGYJWTEPQ-UHFFFAOYSA-N phenyl-(2,3,6-trihydroxyphenyl)methanone Chemical compound OC1=CC=C(O)C(C(=O)C=2C=CC=CC=2)=C1O LSSGAGGYJWTEPQ-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920000636 poly(norbornene) polymer Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001816 polyoxyethylene sorbitan tristearate Substances 0.000 description 1
- 235000010988 polyoxyethylene sorbitan tristearate Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 229940035044 sorbitan monolaurate Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000001589 sorbitan tristearate Substances 0.000 description 1
- 235000011078 sorbitan tristearate Nutrition 0.000 description 1
- 229960004129 sorbitan tristearate Drugs 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KCNSDMPZCKLTQP-UHFFFAOYSA-N tetraphenylen-1-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=CC=CC=C2C2=C1C=CC=C2O KCNSDMPZCKLTQP-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 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
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
Description
R2は、置換基を有していてもよいアルキル基又は置換基を有していてもよいアリール基を表し、nは2〜10の整数を表す。]
で表される分子構造からなることを特徴とする、ナフトール型カリックスアレーン化合物に関する。
で表されるヒドロキシナフタレン類(A)と、下記一般式(3)
で表されるアルデヒド類(B)とを、酸触媒の存在下で反応させてナフトール型カリックスアレーン化合物を得ることを特徴とする、ナフトール型カリックスアレーン化合物の製造方法に関する。
本発明は更に、前記感光性組成物からなるレジスト材料、及び前記感光性組成物からなる塗膜に関する。
樹脂(本発明に係るナフトール型カリックスアレーン化合物を含む。)の分子量分布は、GPCにより、ポリスチレン標準法において、以下の測定条件にて測定した。
測定装置:東ソー株式会社製「HLC−8220 GPC」、
カラム:昭和電工株式会社製「Shodex KF802」(8.0mmI.D.×300mm)
+昭和電工株式会社製「Shodex KF802」(8.0mmI.D.×300mm)
+昭和電工株式会社製「Shodex KF803」(8.0mmI.D.×300mm)
+昭和電工株式会社製「Shodex KF804」(8.0mmI.D.×300mm)、
検出器:ELSD(オルテックジャパン株式会社製「ELSD2000」)、
データ処理:東ソー株式会社製「GPC−8020モデルIIデータ解析バージョン4.30」、
測定条件:カラム温度 40℃
展開溶媒 テトラヒドロフラン(THF)
流速 1.0mL/分
試料:樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(5μL)、
標準試料:前記「GPC−8020モデルIIデータ解析バージョン4.30」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A-2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
東ソー株式会社製「F−288」
東ソー株式会社製「F−550」
樹脂(本発明に係るナフトール型カリックスアレーン化合物を含む。)のFD−MSスペクトルは、日本電子株式会社製の二重収束型質量分析装置「AX505H(FD505H)」を用いて測定した。
温度計、滴下ロート、冷却管、撹拌器を取り付けたフラスコに、1−ナフトール288g、パラアルデヒド107g、2−エトキシエタノール500g、95%硫酸5.8gを仕込み、80℃に昇温後10時間撹拌した。反応終了後、酢酸エチル300g、イオン交換水160gを加えた後、分液漏斗で下層よりpH1の水層を棄却した。イオン交換水160gによる有機層洗浄を7回実施し、棄却される水層がpH4であることを確認した。上層の有機層を、エバポレータを用いて加熱減圧濃縮及び乾燥を行い、目的の前記一般式(1)で表される化合物のうち、nが4であり、R1が水素原子であり、R2がメチル基である化合物がGPC面積比で18%含まれる混合物(1)309gを得た。収率は91%であり、FD−MSスペクトルから環状化合物を示す680のピークが検出された。得られた混合物(1)のGPCスペクトルを図1に示す。
温度計、滴下ロート、冷却管、撹拌器を取り付けたフラスコに、1−ナフトール288g、4−ヒドロキシベンズアルデヒド244g、1−ブタノール500g、95%硫酸14.4gを仕込み、80℃に昇温後17時間撹拌した。反応終了後、酢酸エチル300g、イオン交換水160gを加えた後、分液漏斗で下層よりpH1の水層を棄却した。イオン交換水160gによる有機層洗浄を7回実施し、棄却される水層がpH4であることを確認した。上層の有機層を、エバポレータを用いて加熱減圧濃縮及び乾燥を行い、目的の前記一般式(1)で表される化合物のうち、nが4であり、R1が水素原子であり、R2がヒドロキシフェニル基である化合物がGPC面積比で52%含まれる混合物(2)466gを得た。収率は94%であり、FD−MSスペクトルから環状化合物を示す992のピークが検出された。得られた混合物(2)のGPCスペクトルを図2に示す。
温度計、滴下ロート、冷却管、撹拌器を取り付けたフラスコに、α−ナフトール48g、42質量%ホルムアルデヒド水溶液26g、イソプロピルアルコール50g、48%水酸化ナトリウム9.4gを仕込み、室温下、窒素を吹き込みながら撹拌した。その後、80℃に昇温して1時間撹拌した。反応終了後、第1リン酸ソーダ8gを添加して中和し、冷却して結晶物をろ別した。当該結晶物を水50gで3回洗浄した後、加熱減圧乾燥して比較対照用混合物(1’)47gを得た。
温度計、冷却管、撹拌器を取り付けた1L容の4つ口フラスコに、1−ナフトール144g、メチルイソブチルケトン400g、水96g及び92%パラホルムアルデヒド27.7gを仕込んだ。続いて攪拌しながら、50%濃度に調整したパラトルエンスルホン酸の水溶液4.8gを添加した。その後、攪拌しながら80℃に昇温し、2時間反応させた。反応終了後、系内の溶液を分液ロートに移し水層を有機層から分離除去した。次いで、洗浄水が中性を示すまで水洗後した後、有機層から溶媒を加熱減圧下に除去し、比較対照用ノボラック樹脂(2’)147gを得た。
実施例1〜2及び比較例1〜2で合成した混合物(1)〜(2)、比較対照用混合物(1’)、及び比較対照用ノボラック樹脂(2’)について、表1に示すように、樹脂成分、感光剤〔東洋合成工業製「P−200」、4,4’−[1−[4−[1−(4−ヒドロキシフェニル)−1メチルエチル]フェニル]エチリデン]ビスフェノール(1モル)と1,2−ナフトキノン−2−ジアジド−5−スルホニルクロリド(2モル)の縮合物〕、及びプロピレングリコールモノメチルエーテルアセテート(以下、「PGMEA」と略記する。)を16/4/80(質量部)で混合して溶解させた後、0.2μmメンブランフィルターを用いて濾過し、感光性組成物(ポジ型レジスト組成物)とした。
得られた各ポジ型感光性組成物についての溶剤溶解性を評価すると共に、これらの組成物を用いて得られる塗膜のアルカリ現像性、感度、解像度、及び耐熱分解性を評価した。評価方法は下記の通りとした。
サンプル瓶に、合成例1〜2及び比較合成例1〜2で合成したそれぞれの化合物(又は、樹脂)8gと、感光剤(P−200)2gと、PGMEAとを、溶液濃度20%になるよう加えた後、常温条件下で振とう機にて撹拌した。撹拌後、サンプル瓶内の溶剤の状態を目視で評価した。評価は、均一透明な状態のものを「○」、固形成分が析出又は沈殿した状態のものを「×」とした。
感光性組成物を、5インチシリコンウェハー上に約1μmの厚さになるようにスピンコーターで塗布し、110℃のホットプレート上で60秒間乾燥させて塗膜を有するシリコンウェハーを得た。得られたウェハーを、アルカリ現像液(2.38%水酸化テトラメチルアンモニウム水溶液)に60秒間浸漬させた後、110℃のホットプレート上で60秒間乾燥させた。当該感光性組成物の塗膜の膜厚を、現像液浸漬前後で測定し、その差分を60で除した値をアルカリ現像性(ADR(nm/s))の評価結果とした。露光させる場合は、ghi線ランプ(ウシオ電機社製、マルチライト)で十分に露光される100mJ/cm2照射した後、140℃、60秒間の条件でPEB(Post Exposure Bake)を施したウェハーを用いてADRアルカリ現像性を評価した。
感光性組成物を1μmの厚さで塗布し乾燥させた塗膜を有する5インチシリコンウェハー上に、ラインアンドスペースが1:1の1〜10μmレジストパターン対応のマスクを密着させた後、ghi線ランプで3μmを忠実に再現することのできる露光量(Eop露光量)を求めた。
感光性組成物を塗布し乾燥させた塗膜を有する5インチシリコンウェハー上にフォトマスクを乗せ、ghi線ランプ(ウシオ電機社製、マルチライト)で100mJ/cm2照射し感光せしめた。照射後の塗膜を、<アルカリ現像性評価>と同様にして現像し乾燥させた。現像後のウェハー上のレジストパターンのパターン状態を、キーエンス社製レーザーマイクロスコープ(VK−8500)を用いて評価した。評価は、L/S=3μmで解像できているものを「○」、L/S=3μmで解像できていないものを「×」とした。
感光性組成物を5インチシリコンウェハー上に1μmの厚さになるようにスピンコーターで塗布し、110℃のホットプレート上で60秒間乾燥させて塗膜を有するシリコンウェハーを得た。得られたウェハーより樹脂分をかきとり、Tgを測定した。Tgの測定は、示差熱熱重量同時測定装置(セイコーインスツールメント社製、製品名:TG/DTA 6200)を用いて、窒素雰囲気下、温度範囲:室温〜400℃、昇温温度:10℃/分の条件で、一定速度で昇温時の重量減少を測定し、熱分解開始温度を求めた。
レジスト永久膜への使用を想定して、本発明に係る感光性組成物を評価した。
具体的には、実施例1〜2及び比較例1〜2で合成した混合物(1)〜(2)、比較対照用混合物(1’)、及び比較対照用ノボラック樹脂(2’)について、表2に示すように、樹脂成分、感光剤〔東洋合成工業製「P−200」、4,4’−[1−[4−[1−(4−ヒドロキシフェニル)−1メチルエチル]フェニル]エチリデン]ビスフェノール(1モル)と1,2−ナフトキノン−2−ジアジド−5−スルホニルクロリド(2モル)の縮合物〕、架橋剤〔東京化成工業(株)製1,3,4,6−テトラキス(メトキシメチル)グリコールウリル〕、及びPGMEAを16/3/1/80(質量部)で混合して溶解させた後、0.2μmメンブランフィルターを用いて濾過し、感光性組成物(フォトレジスト永久膜組成物)とした。
得られた各フォトレジスト永久膜組成物についての溶剤溶解性を評価すると共に、これらの組成物を用いて得られる塗膜のアルカリ現像性、感度、解像度、及び耐熱分解性を評価した。評価方法は下記の通りとした。結果を表2に示す。
前記した<溶剤溶解性の評価>に従った。
前記した<アルカリ現像性評価>の評価方法に従った。
前記した<感度評価>の評価方法に従った。
感光性組成物を塗布し乾燥させた塗膜を有する5インチシリコンウェハー上にフォトマスクを乗せ、ghi線ランプ(ウシオ電機社製、マルチライト)で100mJ/cm2照射し感光せしめた。照射後の塗膜を<アルカリ現像性評価>と同様にして現像し乾燥させた。現像後のウェハー上のレジストパターンのパターン状態を、キーエンス社製レーザーマイクロスコープ(VK−8500)を用いて評価した。評価は、レジスト永久膜への使用を想定し、L/S=5μmで解像できているものを「○」、L/S=5μmで解像できていないものを「×」とした。
前記した<耐熱分解性評価>の評価方法に従った。
Claims (16)
- 前記R1が水素原子である、請求項1又は2に記載のナフトール型カリックスアレーン化合物。
- 前記R2がメチル基又はヒドロキシフェニル基である、請求項1〜3のいずれか一項に記載のナフトール型カリックスアレーン化合物。
- 前記nが、2、3、4、5、6、又は8である、請求項1に記載のナフトール型カリックスアレーン化合物。
- 前記ヒドロキシナフタレン類(A)が1−ナフトールであり、前記アルデヒド類(B)がアセトアルデヒド又はヒドロキシベンズアルデヒドである、請求項6に記載のナフトール型カリックスアレーン化合物の製造方法。
- 前記ヒドロキシナフタレン類(A)と前記アルデヒド類(B)とを、反応割合〔(A)/(B)〕がモル比で0.5〜1.5の範囲となる条件で、有機溶剤を含有する系内で、酸触媒下に反応させる、請求項6又は7に記載のナフトール型カリックスアレーン化合物の製造方法。
- 前記酸触媒が、硫酸である、請求項6〜8のいずれか一項に記載のナフトール型カリックスアレーン化合物の製造方法。
- 前記有機溶剤が、2−エトキシエタノール、ブタノール、オクタノール、メチルエチルケトン、及びメチルイソブチルケトンからなる群より選択される1種以上である、請求項8に記載のナフトール型カリックスアレーン化合物の製造方法。
- 請求項1〜5のいずれか一項に記載のナフトール型カリックスアレーン化合物と、感光剤とを含有する感光性組成物。
- 請求項11記載の感光性組成物からなるレジスト材料。
- 請求項11記載の感光性組成物からなる塗膜。
- レジスト膜である、請求項13に記載の塗膜。
- 永久膜である、請求項13に記載の塗膜。
- 下層膜である、請求項13に記載の塗膜。
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US10466590B2 (en) | 2019-11-05 |
CN106795077B (zh) | 2021-03-30 |
TWI675051B (zh) | 2019-10-21 |
JPWO2016056355A1 (ja) | 2017-04-27 |
KR20170066315A (ko) | 2017-06-14 |
WO2016056355A1 (ja) | 2016-04-14 |
US20170329226A1 (en) | 2017-11-16 |
KR102313190B1 (ko) | 2021-10-18 |
TW201623353A (zh) | 2016-07-01 |
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