WO2014208542A1 - 置換された架橋性化合物を含むレジスト下層膜形成組成物 - Google Patents
置換された架橋性化合物を含むレジスト下層膜形成組成物 Download PDFInfo
- Publication number
- WO2014208542A1 WO2014208542A1 PCT/JP2014/066680 JP2014066680W WO2014208542A1 WO 2014208542 A1 WO2014208542 A1 WO 2014208542A1 JP 2014066680 W JP2014066680 W JP 2014066680W WO 2014208542 A1 WO2014208542 A1 WO 2014208542A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- underlayer film
- resist underlayer
- group
- integer
- carbon atoms
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 91
- 150000001875 compounds Chemical class 0.000 title claims abstract description 80
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 71
- 239000000758 substrate Substances 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 40
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 37
- 229920005989 resin Polymers 0.000 claims abstract description 37
- 239000011347 resin Substances 0.000 claims abstract description 37
- 239000004065 semiconductor Substances 0.000 claims abstract description 32
- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000000962 organic group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- -1 ether compound Chemical class 0.000 claims description 149
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 31
- 239000003054 catalyst Substances 0.000 claims description 29
- 239000003431 cross linking reagent Substances 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 24
- 238000010894 electron beam technology Methods 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 12
- 238000005530 etching Methods 0.000 claims description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
- 239000003377 acid catalyst Substances 0.000 claims description 10
- 238000012545 processing Methods 0.000 claims description 10
- 238000011161 development Methods 0.000 claims description 9
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 8
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical group C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003456 ion exchange resin Substances 0.000 claims description 7
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 7
- 229920003986 novolac Polymers 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 5
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 claims description 4
- 229940093475 2-ethoxyethanol Drugs 0.000 claims description 4
- 238000000151 deposition Methods 0.000 claims description 3
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 3
- 229910010272 inorganic material Inorganic materials 0.000 claims 2
- 239000011147 inorganic material Substances 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 238000001459 lithography Methods 0.000 abstract description 39
- 238000001312 dry etching Methods 0.000 abstract description 7
- 239000010408 film Substances 0.000 description 156
- 230000015572 biosynthetic process Effects 0.000 description 49
- 239000000243 solution Substances 0.000 description 47
- 238000003786 synthesis reaction Methods 0.000 description 47
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 36
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 33
- 239000004698 Polyethylene Substances 0.000 description 30
- 229920000573 polyethylene Polymers 0.000 description 30
- 239000011148 porous material Substances 0.000 description 30
- 239000004094 surface-active agent Substances 0.000 description 21
- 229920002120 photoresistant polymer Polymers 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 18
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 18
- 238000004132 cross linking Methods 0.000 description 16
- 238000000859 sublimation Methods 0.000 description 16
- 230000008022 sublimation Effects 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 238000000576 coating method Methods 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 235000012431 wafers Nutrition 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 239000013077 target material Substances 0.000 description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000004090 dissolution Methods 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 238000003380 quartz crystal microbalance Methods 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000006096 absorbing agent Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000031700 light absorption Effects 0.000 description 3
- 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 3
- 238000010992 reflux Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 150000003585 thioureas Chemical class 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- DLDWUFCUUXXYTB-UHFFFAOYSA-N (2-oxo-1,2-diphenylethyl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C=1C=CC=CC=1)C(=O)C1=CC=CC=C1 DLDWUFCUUXXYTB-UHFFFAOYSA-N 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 2
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 2
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 2
- 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 2
- RJWBTWIBUIGANW-UHFFFAOYSA-N 4-chlorobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)C=C1 RJWBTWIBUIGANW-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-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 description 2
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical compound OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 0 C*1=CCCC1 Chemical compound C*1=CCCC1 0.000 description 2
- KCXZNSGUUQJJTR-UHFFFAOYSA-N Di-n-hexyl phthalate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCC KCXZNSGUUQJJTR-UHFFFAOYSA-N 0.000 description 2
- NIQCNGHVCWTJSM-UHFFFAOYSA-N Dimethyl phthalate Chemical compound COC(=O)C1=CC=CC=C1C(=O)OC NIQCNGHVCWTJSM-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-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
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004115 Sodium Silicate Substances 0.000 description 2
- 235000002597 Solanum melongena Nutrition 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004849 alkoxymethyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 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
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- YNKMHABLMGIIFX-UHFFFAOYSA-N benzaldehyde;methane Chemical compound C.O=CC1=CC=CC=C1 YNKMHABLMGIIFX-UHFFFAOYSA-N 0.000 description 2
- MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 2
- 229960001231 choline Drugs 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- MGWAVDBGNNKXQV-UHFFFAOYSA-N diisobutyl phthalate Chemical compound CC(C)COC(=O)C1=CC=CC=C1C(=O)OCC(C)C MGWAVDBGNNKXQV-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 238000005755 formation reaction Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- 125000001046 glycoluril group Chemical class [H]C12N(*)C(=O)N(*)C1([H])N(*)C(=O)N2* 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 150000007974 melamines Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000002952 polymeric resin Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000006254 rheological additive Substances 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 2
- 229910052911 sodium silicate Inorganic materials 0.000 description 2
- 235000019337 sorbitan trioleate Nutrition 0.000 description 2
- 229960000391 sorbitan trioleate Drugs 0.000 description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- JWSIJFDOWHFZTK-UHFFFAOYSA-N (2-formylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C=O JWSIJFDOWHFZTK-UHFFFAOYSA-N 0.000 description 1
- CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 1
- MCVVDMSWCQUKEV-UHFFFAOYSA-N (2-nitrophenyl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1=CC=CC=C1[N+]([O-])=O MCVVDMSWCQUKEV-UHFFFAOYSA-N 0.000 description 1
- 239000001893 (2R)-2-methylbutanal Substances 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 description 1
- QMMJWQMCMRUYTG-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=C(Cl)C(Cl)=CC(Cl)=C1Cl QMMJWQMCMRUYTG-UHFFFAOYSA-N 0.000 description 1
- UDATXMIGEVPXTR-UHFFFAOYSA-N 1,2,4-triazolidine-3,5-dione Chemical compound O=C1NNC(=O)N1 UDATXMIGEVPXTR-UHFFFAOYSA-N 0.000 description 1
- MASDFXZJIDNRTR-UHFFFAOYSA-N 1,3-bis(trimethylsilyl)urea Chemical compound C[Si](C)(C)NC(=O)N[Si](C)(C)C MASDFXZJIDNRTR-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- OXFSTTJBVAAALW-UHFFFAOYSA-N 1,3-dihydroimidazole-2-thione Chemical compound SC1=NC=CN1 OXFSTTJBVAAALW-UHFFFAOYSA-N 0.000 description 1
- 229940057054 1,3-dimethylurea Drugs 0.000 description 1
- MUVQKFGNPGZBII-UHFFFAOYSA-N 1-anthrol Chemical compound C1=CC=C2C=C3C(O)=CC=CC3=CC2=C1 MUVQKFGNPGZBII-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical group CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- FUWDFGKRNIDKAE-UHFFFAOYSA-N 1-butoxypropan-2-yl acetate Chemical compound CCCCOCC(C)OC(C)=O FUWDFGKRNIDKAE-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- 125000006433 1-ethyl cyclopropyl group Chemical group [H]C([H])([H])C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- QPAWHGVDCJWYRJ-UHFFFAOYSA-N 1-hydroxypyrrolidine-2,5-dione;trifluoromethanesulfonic acid Chemical compound ON1C(=O)CCC1=O.OS(=O)(=O)C(F)(F)F QPAWHGVDCJWYRJ-UHFFFAOYSA-N 0.000 description 1
- 125000006438 1-i-propyl cyclopropyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- 125000006439 1-n-propyl cyclopropyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- IOVNHINTOHPELQ-UHFFFAOYSA-N 1-o-butyl 2-o-(8-methylnonyl) benzene-1,2-dicarboxylate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC(C)C IOVNHINTOHPELQ-UHFFFAOYSA-N 0.000 description 1
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- NJQJGRGGIUNVAB-UHFFFAOYSA-N 2,4,4,6-tetrabromocyclohexa-2,5-dien-1-one Chemical compound BrC1=CC(Br)(Br)C=C(Br)C1=O NJQJGRGGIUNVAB-UHFFFAOYSA-N 0.000 description 1
- DGPBVJWCIDNDPN-UHFFFAOYSA-N 2-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=CC=C1C=O DGPBVJWCIDNDPN-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 description 1
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- KLLLJCACIRKBDT-UHFFFAOYSA-N 2-phenyl-1H-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CC=C1 KLLLJCACIRKBDT-UHFFFAOYSA-N 0.000 description 1
- HAZQZUFYRLFOLC-UHFFFAOYSA-N 2-phenyl-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=2C=CC=CC=2)=N1 HAZQZUFYRLFOLC-UHFFFAOYSA-N 0.000 description 1
- HCGFUIQPSOCUHI-UHFFFAOYSA-N 2-propan-2-yloxyethanol Chemical compound CC(C)OCCO HCGFUIQPSOCUHI-UHFFFAOYSA-N 0.000 description 1
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- BCPQALWAROJVLE-UHFFFAOYSA-N 4-(2,4-dinitroanilino)phenol Chemical compound C1=CC(O)=CC=C1NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O BCPQALWAROJVLE-UHFFFAOYSA-N 0.000 description 1
- YFVXLROHJBSEDW-UHFFFAOYSA-N 4-[(4-nitrophenyl)diazenyl]-n-phenylaniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1N=NC(C=C1)=CC=C1NC1=CC=CC=C1 YFVXLROHJBSEDW-UHFFFAOYSA-N 0.000 description 1
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- ZBSKZKPSSKTLNE-UHFFFAOYSA-N 4-methylpent-3-enoxysilane Chemical compound CC(=CCCO[SiH3])C ZBSKZKPSSKTLNE-UHFFFAOYSA-N 0.000 description 1
- XZIIFPSPUDAGJM-UHFFFAOYSA-N 6-chloro-2-n,2-n-diethylpyrimidine-2,4-diamine Chemical compound CCN(CC)C1=NC(N)=CC(Cl)=N1 XZIIFPSPUDAGJM-UHFFFAOYSA-N 0.000 description 1
- NWSGBTCJMJADLE-UHFFFAOYSA-N 6-o-decyl 1-o-octyl hexanedioate Chemical compound CCCCCCCCCCOC(=O)CCCCC(=O)OCCCCCCCC NWSGBTCJMJADLE-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- AHJKRLASYNVKDZ-UHFFFAOYSA-N DDD Chemical compound C=1C=C(Cl)C=CC=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 AHJKRLASYNVKDZ-UHFFFAOYSA-N 0.000 description 1
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- XTJFFFGAUHQWII-UHFFFAOYSA-N Dibutyl adipate Chemical compound CCCCOC(=O)CCCCC(=O)OCCCC XTJFFFGAUHQWII-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- RDOFJDLLWVCMRU-UHFFFAOYSA-N Diisobutyl adipate Chemical compound CC(C)COC(=O)CCCCC(=O)OCC(C)C RDOFJDLLWVCMRU-UHFFFAOYSA-N 0.000 description 1
- FOQABOMYTOFLPZ-ISLYRVAYSA-N Disperse Red 1 Chemical compound C1=CC(N(CCO)CC)=CC=C1\N=N\C1=CC=C([N+]([O-])=O)C=C1 FOQABOMYTOFLPZ-ISLYRVAYSA-N 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 1
- STNJBCKSHOAVAJ-UHFFFAOYSA-N Methacrolein Chemical compound CC(=C)C=O STNJBCKSHOAVAJ-UHFFFAOYSA-N 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- YKFRUJSEPGHZFJ-UHFFFAOYSA-N N-trimethylsilylimidazole Chemical compound C[Si](C)(C)N1C=CN=C1 YKFRUJSEPGHZFJ-UHFFFAOYSA-N 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N N-undecane Natural products CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 1
- 229910008045 Si-Si Inorganic materials 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 229910006411 Si—Si Inorganic materials 0.000 description 1
- 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 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
- XQBQVMYWVQLMHW-UHFFFAOYSA-N [dinitro(phenyl)methyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC([N+]([O-])=O)([N+]([O-])=O)C1=CC=CC=C1 XQBQVMYWVQLMHW-UHFFFAOYSA-N 0.000 description 1
- STOLYTNTPGXYRW-UHFFFAOYSA-N [nitro(phenyl)methyl] 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC([N+]([O-])=O)C1=CC=CC=C1 STOLYTNTPGXYRW-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001278 adipic acid derivatives Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000006117 anti-reflective coating Substances 0.000 description 1
- 150000003934 aromatic aldehydes Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- XWEVKPKISJJUAH-UHFFFAOYSA-N benzenethiol;trifluoromethanesulfonic acid Chemical compound [SH2+]C1=CC=CC=C1.[O-]S(=O)(=O)C(F)(F)F XWEVKPKISJJUAH-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- CJFLBOQMPJCWLR-UHFFFAOYSA-N bis(6-methylheptyl) hexanedioate Chemical compound CC(C)CCCCCOC(=O)CCCCC(=O)OCCCCCC(C)C CJFLBOQMPJCWLR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- BQFCCCIRTOLPEF-UHFFFAOYSA-N chembl1976978 Chemical compound CC1=CC=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 BQFCCCIRTOLPEF-UHFFFAOYSA-N 0.000 description 1
- ALLOLPOYFRLCCX-UHFFFAOYSA-N chembl1986529 Chemical compound COC1=CC=CC=C1N=NC1=C(O)C=CC2=CC=CC=C12 ALLOLPOYFRLCCX-UHFFFAOYSA-N 0.000 description 1
- ITKVLPYNJQOCPW-UHFFFAOYSA-N chloro-(chloromethyl)-dimethylsilane Chemical compound C[Si](C)(Cl)CCl ITKVLPYNJQOCPW-UHFFFAOYSA-N 0.000 description 1
- XSDCTSITJJJDPY-UHFFFAOYSA-N chloro-ethenyl-dimethylsilane Chemical compound C[Si](C)(Cl)C=C XSDCTSITJJJDPY-UHFFFAOYSA-N 0.000 description 1
- OJZNZOXALZKPEA-UHFFFAOYSA-N chloro-methyl-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C)C1=CC=CC=C1 OJZNZOXALZKPEA-UHFFFAOYSA-N 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 229940031769 diisobutyl adipate Drugs 0.000 description 1
- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
- PKTOVQRKCNPVKY-UHFFFAOYSA-N dimethoxy(methyl)silicon Chemical compound CO[Si](C)OC PKTOVQRKCNPVKY-UHFFFAOYSA-N 0.000 description 1
- FBSAITBEAPNWJG-UHFFFAOYSA-N dimethyl phthalate Natural products CC(=O)OC1=CC=CC=C1OC(C)=O FBSAITBEAPNWJG-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 229960001826 dimethylphthalate Drugs 0.000 description 1
- PQJYOOFQDXGDDS-ZCXUNETKSA-N dinonyl (z)-but-2-enedioate Chemical compound CCCCCCCCCOC(=O)\C=C/C(=O)OCCCCCCCCC PQJYOOFQDXGDDS-ZCXUNETKSA-N 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical class C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- 229940042397 direct acting antivirals cyclic amines Drugs 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- LRMHFDNWKCSEQU-UHFFFAOYSA-N ethoxyethane;phenol Chemical compound CCOCC.OC1=CC=CC=C1 LRMHFDNWKCSEQU-UHFFFAOYSA-N 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- CKSRFHWWBKRUKA-UHFFFAOYSA-N ethyl 2-ethoxyacetate Chemical compound CCOCC(=O)OCC CKSRFHWWBKRUKA-UHFFFAOYSA-N 0.000 description 1
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 description 1
- ZANNOFHADGWOLI-UHFFFAOYSA-N ethyl 2-hydroxyacetate Chemical compound CCOC(=O)CO ZANNOFHADGWOLI-UHFFFAOYSA-N 0.000 description 1
- IJUHLFUALMUWOM-UHFFFAOYSA-N ethyl 3-methoxypropanoate Chemical compound CCOC(=O)CCOC IJUHLFUALMUWOM-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 238000001900 extreme ultraviolet lithography Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940075529 glyceryl stearate Drugs 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000003993 interaction Effects 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 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
- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- WIBFFTLQMKKBLZ-SEYXRHQNSA-N n-butyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCCCC WIBFFTLQMKKBLZ-SEYXRHQNSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 125000001298 n-hexoxy 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- KAHVZNKZQFSBFW-UHFFFAOYSA-N n-methyl-n-trimethylsilylmethanamine Chemical compound CN(C)[Si](C)(C)C KAHVZNKZQFSBFW-UHFFFAOYSA-N 0.000 description 1
- 125000003935 n-pentoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CXAYOCVHDCXPAI-UHFFFAOYSA-N naphthalen-1-yl(phenyl)methanone Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)C1=CC=CC=C1 CXAYOCVHDCXPAI-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- DCUJJWWUNKIJPH-UHFFFAOYSA-N nitrapyrin Chemical compound ClC1=CC=CC(C(Cl)(Cl)Cl)=N1 DCUJJWWUNKIJPH-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 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
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- GIPDEPRRXIBGNF-KTKRTIGZSA-N oxolan-2-ylmethyl (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC1CCCO1 GIPDEPRRXIBGNF-KTKRTIGZSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 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
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 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
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- RCYFOPUXRMOLQM-UHFFFAOYSA-N pyrene-1-carbaldehyde Chemical compound C1=C2C(C=O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 RCYFOPUXRMOLQM-UHFFFAOYSA-N 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019795 sodium metasilicate Nutrition 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
- 239000001570 sorbitan monopalmitate Substances 0.000 description 1
- 235000011071 sorbitan monopalmitate Nutrition 0.000 description 1
- 229940031953 sorbitan monopalmitate 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
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940072958 tetrahydrofurfuryl oleate Drugs 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- ZEMGGZBWXRYJHK-UHFFFAOYSA-N thiouracil Chemical compound O=C1C=CNC(=S)N1 ZEMGGZBWXRYJHK-UHFFFAOYSA-N 0.000 description 1
- 229950000329 thiouracil Drugs 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- ULAQISQDFQAUCH-UHFFFAOYSA-N trifluoromethanesulfonic acid hydroiodide Chemical compound I.OS(=O)(=O)C(F)(F)F ULAQISQDFQAUCH-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical class C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Images
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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/10—Polyhydroxy benzenes; Alkylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
- C07C43/1785—Unsaturated ethers containing hydroxy or O-metal groups having more than one ether bound
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/06—Amines
- C08G12/08—Amines aromatic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/04—Condensation polymers of aldehydes or ketones with phenols only
- C09D161/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D161/00—Coating compositions based on condensation polymers of aldehydes or ketones; Coating compositions based on derivatives of such polymers
- C09D161/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C09D161/22—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/091—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers characterised by antireflection means or light filtering or absorbing means, e.g. anti-halation, contrast enhancement
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/094—Multilayer resist systems, e.g. planarising layers
-
- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
-
- 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
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/3105—After-treatment
- H01L21/311—Etching the insulating layers by chemical or physical means
- H01L21/31127—Etching organic layers
- H01L21/31133—Etching organic layers by chemical means
- H01L21/31138—Etching organic layers by chemical means by dry-etching
-
- 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
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/3105—After-treatment
- H01L21/311—Etching the insulating layers by chemical or physical means
- H01L21/31144—Etching the insulating layers by chemical or physical means using masks
Definitions
- the present invention relates to a crosslinking catalyst for a resist underlayer film forming composition for lithography effective at the time of processing a semiconductor substrate, a resist underlayer film forming composition containing the same, a resist pattern forming method using the resist underlayer film forming composition, and
- the present invention relates to a method for manufacturing a semiconductor device.
- a thin film of a photoresist composition is formed on a substrate to be processed such as a silicon wafer, and irradiated with actinic rays such as ultraviolet rays through a mask pattern on which a semiconductor device pattern is drawn, and developed.
- actinic rays such as ultraviolet rays
- This is a processing method for etching a substrate to be processed such as a silicon wafer using the obtained photoresist pattern as a protective film.
- EUV lithography and EB lithography generally do not require a specific anti-reflection film because they do not cause diffuse reflection or standing wave from the substrate, but an auxiliary film for the purpose of improving the resolution and adhesion of the resist pattern As such, the resist underlayer film has begun to be widely studied.
- Such a resist underlayer film formed between the photoresist and the substrate to be processed is generally applied on the substrate to be processed in order to suppress mixing with the resist laminated on the upper layer.
- the film is formed as a thermosetting crosslinked film that does not cause mixing with the resist through the baking process.
- thermosetting film in a resist underlayer film forming composition in addition to a polymer resin as a main component, a crosslinking compound (crosslinking agent) and a catalyst for promoting a crosslinking reaction (crosslinking catalyst) ) Is blended.
- a crosslinking catalyst a thermal acid generator such as a sulfonic acid compound, a carboxylic acid compound, or a sulfonic acid ester is mainly used.
- An object of the present invention is to provide a resist underlayer film forming composition for use in a lithography process for manufacturing a semiconductor device.
- the present invention provides a composition for forming a resist underlayer film that is less likely to generate sublimates and has good embedding properties when applied to a substrate having a hole pattern.
- a resin and the following formula (1) or formula (2) (In the formula, Q 1 represents a single bond or an m1-valent organic group, and R 1 and R 4 each represent an alkyl group having 2 to 10 carbon atoms, or a carbon atom number having an alkoxy group having 1 to 10 carbon atoms.
- R 2 and R 5 each represent a hydrogen atom or a methyl group, R 3 and R 6 each represent an alkyl group having 1 to 10 carbon atoms, or an aryl having 6 to 40 carbon atoms Indicates a group.
- n1 is an integer 1 ⁇ n1 ⁇ 3
- n2 is an integer 2 ⁇ n2 ⁇ 5
- n3 is an integer 0 ⁇ n3 ⁇ 3
- n4 is an integer 0 ⁇ n4 ⁇ 3
- n5 is an integer 1 ⁇ n5 ⁇ 3
- n6 is an integer 1 ⁇ n6 ⁇ 4
- n7 is an integer 0 ⁇ n7 ⁇
- n8 is an integer 0 ⁇ n8 ⁇ 3
- m1 represents an integer of 2 to 10.
- a resist underlayer film-forming composition comprising a crosslinkable compound represented by As a second aspect, Q 1 is a single bond or an m1-valent organic group selected from a chain hydrocarbon group having 1 to 10 carbon atoms, an aromatic group having 6 to 40 carbon atoms, or a combination thereof.
- the resist underlayer film forming composition according to the first aspect As a third aspect, the crosslinkable compound represented by the above formula (1) or formula (2) is a compound represented by the following formula (3) or formula (4), a hydroxyl group-containing ether compound, or 2 to 2 carbon atoms.
- the resist underlayer film forming composition according to the first aspect or the second aspect which is obtained by reaction with 10 alcohols, (In the formula, Q 2 represents a single bond or an m2-valent organic group.
- R 8 , R 9 , R 11 and R 12 each represent a hydrogen atom or a methyl group, and R 7 and R 10 each have 1 carbon atom.
- n9 is an integer of 1 ⁇ n9 ⁇ 3
- n10 is an integer of 2 ⁇ n10 ⁇ 5
- n11 is an integer of 0 ⁇ n11 ⁇ 3
- n12 is an integer of 0 ⁇ n12 ⁇ 3
- 3 ⁇ (n9 + n10 + n11 + n12) ⁇ 6 Show.
- n13 is an integer 1 ⁇ n13 ⁇ 3
- n14 is an integer 1 ⁇ n14 ⁇ 4
- n15 is an integer 0 ⁇ n15 ⁇ 3
- n16 is an integer 0 ⁇ n16 ⁇ 3
- Show. m2 represents an integer of 2 to 10.
- a step of forming a resist underlayer film on the semiconductor substrate with the resist underlayer film forming composition according to any one of the first to tenth aspects, a step of forming a resist film thereon, light Or a step of forming a resist pattern by electron beam irradiation and development, a step of etching the resist underlayer film with the formed resist pattern, and a step of processing a semiconductor substrate with the patterned resist underlayer film.
- a step of forming a resist underlayer film on the semiconductor substrate with the resist underlayer film forming composition according to any one of the first to tenth aspects, a step of forming a hard mask thereon, A step of forming a resist film thereon, a step of forming a resist pattern by irradiation and development of light or electron beam, a step of etching a hard mask by the formed resist pattern, and a layer of the resist underlayer film by a patterned hard mask
- a method of manufacturing a semiconductor device including a step of etching a semiconductor substrate with a patterned resist underlayer film
- the hard mask is formed by inorganic coating or inorganic deposition, and the manufacturing method according to the fourteenth aspect, and the sixteenth aspect, the following formula (5): (Wherein Q 3 represents an isopropylidene group, R 14 represents an alkyl group having 2 to 10 carbon atoms, or an alkyl group having 2 to 10 carbon atom
- n17 is an integer of 1 ⁇ n17 ⁇ 3
- n18 is an integer of 1 ⁇ n18 ⁇ 4
- n19 is an integer of 0 ⁇ n19 ⁇ 3
- n20 is an integer of 0 ⁇ n20 ⁇ 3
- the crosslinkable compound used in the present invention has an alkyl group portion of an alkoxymethyl group (for example, a low molecular weight alkyl group such as a methyl group), a long-chain alkyl group having 2 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms. It is a crosslinkable compound obtained by substituting an alkyl group having 2 to 10 carbon atoms having a group.
- the leaving component desorbed from the crosslinkable compound becomes a compound having a large molecular weight corresponding to the alkyl group moiety.
- crosslinked compound of this invention is coat
- the alkyl group portion of the alkoxymethyl group (for example, a low molecular weight alkyl group such as a methyl group) is substituted with a long-chain alkyl group having 2 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms.
- the crosslinkable compound obtained by substituting with 10 to 10 alkyl groups undergoes a slow crosslinking reaction with the resin. For this reason, when the resist underlayer film-forming composition containing the crosslinkable compound of the present invention is coated on a fine hole pattern, a decrease in fluidity accompanying three-dimensionalization due to crosslinking does not occur for a while after coating. Therefore, by using the composition of the present invention, the resist underlayer film forming composition can be filled in the hole pattern without any gap.
- 4 shows the NMR spectrum of the 4-substituted product of TBOM-BIP-A obtained in Synthesis Example 4.
- 1 shows the NMR spectrum of the 4-substituted product of TPOM-BIP-A obtained in Synthesis Example 5.
- 4 is an NMR spectrum of the tetrasubstituted TEOM-BIP-A obtained in Synthesis Example 6.
- 4 is an NMR spectrum of a 4-substitution product of TIBOM-BIP-A obtained in Synthesis Example 7.
- FIG. 4 is an NMR spectrum of the 4-substituted product of EGME-BIP-A obtained in Synthesis Example 8.
- 4 is an NMR spectrum of the 4-substituted product of EGEE-BIP-A obtained in Synthesis Example 9.
- 4 is an NMR spectrum of the 4-substituted product of PGME-BIP-A obtained in Synthesis Example 10.
- 1 shows the NMR spectrum of the 4-substituted product of EGIPE-BIP-A obtained in Synthesis Example 11.
- the present invention relates to a resist underlayer film forming composition containing a resin and a crosslinkable compound represented by formula (1) or formula (2).
- the resist underlayer film forming composition in the present invention generally contains a resin, a crosslinkable compound represented by formula (1) or formula (2), and a solvent. Furthermore, additives such as an acid generator and a surfactant can be included as necessary.
- the solid content of the composition is 0.1 to 70% by mass, or 0.1 to 60% by mass. The solid content is the content ratio of all components excluding the solvent from the resist underlayer film forming composition.
- a resin (polymer) can be contained in the solid content in a proportion of 1 to 99.9% by mass, or 50 to 99.9% by mass, or 50 to 95% by mass, or 50 to 90% by mass.
- crosslinkable compound represented by the formula (1) or the formula (2) in the solid content is 0.01 to 50% by mass, 0.01 to 40% by mass, or 0.1 to 30% by mass. Can be contained.
- the polymer used in the present invention has a weight average molecular weight of 600 to 1000000 or 600 to 200000.
- Q 1 represents a single bond or an m1-valent organic group
- R 1 and R 4 each have 2 to 10 carbon atoms.
- R 2 and R 5 each represent a hydrogen atom or a methyl group
- R 3 and R 6 each represent carbon.
- An alkyl group having 1 to 10 atoms or an aryl group having 6 to 40 carbon atoms is shown.
- n1 is an integer 1 ⁇ n1 ⁇ 3
- n2 is an integer 2 ⁇ n2 ⁇ 5
- n3 is an integer 0 ⁇ n3 ⁇ 3
- n4 is an integer 0 ⁇ n4 ⁇ 3
- n5 is an integer 1 ⁇ n5 ⁇ 3
- n6 is an integer 1 ⁇ n6 ⁇ 4
- n7 is an integer 0 ⁇ n7 ⁇
- n8 is an integer 0 ⁇ n8 ⁇ 3
- m1 represents an integer of 2 to 10.
- Q 1 is a single bond or an m1-valent organic group selected from a chain hydrocarbon group having 1 to 10 carbon atoms, an aromatic group having 6 to 40 carbon atoms, or a combination thereof.
- examples of the chain hydrocarbon group include the following alkyl groups.
- the aromatic group can include the following aryl groups.
- alkyl group having 2 to 10 carbon atoms examples include ethyl group, n-propyl group, i-propyl group, cyclopropyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, and cyclobutyl.
- alkoxy group having 1 to 10 carbon atoms examples include methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, i-butoxy group, s-butoxy group, t-butoxy group, and n-pentoxy group.
- the crosslinkable compound represented by the formula (1) or the formula (2) is a reaction of the compound represented by the formula (3) or the formula (4) with a hydroxyl group-containing ether compound or an alcohol having 2 to 10 carbon atoms.
- the compound represented by the formula (1) or the formula (2) in which the compound represented by the formula (1) or the formula (2) substituted by 2 moles in the same manner, the compound represented by the formula (1) or the formula (2) in the same manner is substituted by 3 moles.
- the compound represented by formula (1) or formula (2) in which 4 moles are substituted in the same manner is defined as a 4-substituted product.
- Q 2 represents a single bond or an m2 valent organic group. That is, the Q 2 is a single bond, or a m2-valent organic group selected from a chain hydrocarbon group having 1 to 10 carbon atoms, an aromatic group having 6 to 40 carbon atoms, or a combination thereof. can do.
- examples of the chain hydrocarbon group include the above alkyl groups.
- An aromatic group can mention the said aryl group.
- R 8 , R 9 , R 11 and R 12 each represent a hydrogen atom or a methyl group
- R 7 and R 10 each represent an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 40 carbon atoms. .
- n9 is an integer of 1 ⁇ n9 ⁇ 3
- n10 is an integer of 2 ⁇ n10 ⁇ 5
- n11 is an integer of 0 ⁇ n11 ⁇ 3
- n12 is an integer of 0 ⁇ n12 ⁇ 3
- n13 is an integer 1 ⁇ n13 ⁇ 3
- n14 is an integer 1 ⁇ n14 ⁇ 4
- n15 is an integer 0 ⁇ n15 ⁇ 3
- n16 is an integer 0 ⁇ n16 ⁇ 3
- m2 represents an integer of 2 to 10.
- Examples of the acid catalyst used here include p-toluenesulfonic acid, trifluoromethanesulfonic acid, pyridinium p-toluenesulfonic acid, salicylic acid, 5-sulfosalicylic acid, 4-phenolsulfonic acid, camphorsulfonic acid, 4-chlorobenzenesulfonic acid, Acidic compounds such as benzenedisulfonic acid, 1-naphthalenesulfonic acid, citric acid, benzoic acid, hydroxybenzoic acid, and naphthalenecarboxylic acid can be used. However, an ion exchange resin for a catalyst can be used in order not to leave unreacted acid in the reaction system.
- the catalyst ion exchange resin for example, a sulfonic acid type strong acid ion exchange resin can be used.
- the hydroxyl group-containing ether compound include propylene glycol monomethyl ether and propylene glycol monoethyl ether.
- the alcohol having 2 to 10 carbon atoms include ethanol, 1-propanol, 2-methyl-1-propanol, butanol, 2-methoxyethanol and 2-ethoxyethanol.
- crosslinkable compounds represented by the formulas (1) and (2) used in the present invention are as follows.
- the resin used in the present invention may be any resin that can form a crosslinking reaction with the crosslinkable compound.
- the cross-linking group present in the resin include a hydroxyl group, a carboxyl group, an amino group, and an alkoxy group.
- the resin having a cross-linking group include an acrylic resin and a novolac resin, and a novolac resin can be preferably used.
- the novolak resin is obtained by reacting an aromatic ring-containing compound with an aldehyde or ketone compound in the presence of an acid catalyst.
- aromatic ring-containing compounds include benzene, phenol, naphthalene, phloroglicinol, hydroxynaphthalene, fluorene, carbazole, bisphenol, bisphenol S, diphenylamine, triphenylamine, phenylnaphthylamine, anthracene, hydroxyanthracene, phenothiazine, phenoxazine, and phenylindole. And polyphenols.
- aldehydes formaldehyde, paraformaldehyde, acetaldehyde, propylaldehyde, butyraldehyde, isobutyraldehyde, valeraldehyde, capronaldehyde, 2-methylbutyraldehyde, hexylaldehyde, undecane aldehyde, 7-methoxy-3, 7-dimethyloctylaldehyde , Cycloaliphatic aldehyde, 3-methyl-2-butyraldehyde, glyoxal, malonaldehyde, succinaldehyde, glutaraldehyde, adipine aldehyde and other saturated aliphatic aldehydes, acrolein, methacrolein and other unsaturated aliphatic aldehydes, furfural , Heterocyclic aldehydes such as pyridine aldehyde, benzy
- ketone examples include diaryl ketones such as diphenyl ketone, phenyl naphthyl ketone, dinaphthyl ketone, phenyl tolyl ketone, ditolyl ketone, and 9-fluorenone.
- the novolak resin used in the present invention is a resin obtained by condensing an aromatic ring-containing compound with aldehydes or ketones.
- aldehydes or ketones can be used at a ratio of 0.1 to 10 equivalents with respect to 1 equivalent of the phenyl group included in the heterocyclic group-containing aromatic compound and involved in the reaction.
- Examples of the acid catalyst used in the above condensation reaction include mineral acids such as sulfuric acid, phosphoric acid and perchloric acid, organic sulfonic acids such as p-toluenesulfonic acid and p-toluenesulfonic acid monohydrate, formic acid and oxalic acid. Carboxylic acids such as are used.
- the amount of the acid catalyst used is variously selected depending on the type of acids used. Usually, it is 0.001 to 10000 parts by mass, preferably 0.01 to 1000 parts by mass, and more preferably 0.1 to 100 parts by mass with respect to 100 parts by mass of the aromatic ring-containing compound.
- the above condensation reaction is carried out without a solvent, but is usually carried out using a solvent. Any solvent that does not inhibit the reaction can be used. Examples thereof include cyclic ethers such as tetrahydrofuran and dioxane.
- the acid catalyst used is a liquid such as formic acid, it can also serve as a solvent.
- the reaction temperature during the condensation is usually 40 ° C to 200 ° C.
- the reaction time is variously selected depending on the reaction temperature, but is usually about 30 minutes to 50 hours.
- p-toluenesulfonic acid trifluoromethanesulfonic acid, pyridinium p-toluenesulfonic acid, a catalyst for promoting the crosslinking reaction between the resin and the crosslinkable compound represented by formula (1) or (2)
- Acidic compounds such as salicylic acid, 5-sulfosalicylic acid, 4-phenolsulfonic acid, camphorsulfonic acid, 4-chlorobenzenesulfonic acid, benzenedisulfonic acid, 1-naphthalenesulfonic acid, citric acid, benzoic acid, hydroxybenzoic acid, naphthalenecarboxylic acid And / or thermal acid generators such as 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate, and other organic sulfonic acid alkyl esters, or bis (4-t-butylphenyl) )
- crosslinking agent other than the crosslinking agent compound represented by formula (1) or formula (2) can be contained.
- crosslinking agents include melamine-based, substituted urea-based, or polymer-based ones thereof.
- a cross-linking agent having at least two cross-linking substituents, methoxymethylated glycoluril, butoxymethylated glycoluril, methoxymethylated melamine, butoxymethylated melamine, methoxymethylated benzogwanamine, butoxymethylated benzogwanamine, Compounds such as methoxymethylated urea, butoxymethylated urea, methoxymethylated thiourea, or methoxymethylated thiourea. Moreover, the condensate of these compounds can also be used.
- Examples of further light absorbers include commercially available light absorbers described in “Technical dye technology and market” (published by CMC) and “Dye Handbook” (edited by the Society of Synthetic Organic Chemistry), such as C.I. I. Disperse Yellow 1, 3, 4, 5, 7, 8, 13, 23, 31, 49, 50, 51, 54, 60, 64, 66, 68, 79, 82, 88, 90, 93, 102, 114 and 124; C. I. Disperse Orange 1, 5, 13, 25, 29, 30, 31, 44, 57, 72 and 73; I. Disperse Red 1, 5, 7, 13, 17, 19, 43, 50, 54, 58, 65, 72, 73, 88, 117, 137, 143, 199 and 210; I.
- DisperseViolet 43; C.I. I. DisperseBlue 96; C.I. I. Fluorescent BrighteningBAgent 112, 135 and 163; I. Solvent Orange 2 and 45; C.I. I. Solvent Red 1, 3, 8, 23, 24, 25, 27 and 49; I. Pigment Green 10; C.I. I. Pigment Brown 2 etc. can be used suitably.
- the above light-absorbing agent is usually blended at a ratio of 10% by mass or less, preferably 5% by mass or less, based on the total solid content of the resist underlayer film forming composition for lithography.
- the rheology modifier mainly improves the fluidity of the resist underlayer film forming composition, and improves the film thickness uniformity of the resist underlayer film and the fillability of the resist underlayer film forming composition inside the hole, particularly in the baking process. It is added for the purpose of enhancing.
- phthalic acid derivatives such as dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, dihexyl phthalate, butyl isodecyl phthalate, adipic acid derivatives such as dinormal butyl adipate, diisobutyl adipate, diisooctyl adipate, octyl decyl adipate
- maleic acid derivatives such as normal butyl maleate, diethyl maleate and dinonyl maleate
- oleic acid derivatives such as methyl oleate, butyl oleate and tetrahydrofurfuryl oleate
- stearic acid derivatives such as normal butyl stearate and glyceryl stearate. it can.
- These rheology modifiers are usually blended at a ratio of less than 30% by mass with respect to the total solid content of the resist underlayer film forming
- the adhesion assistant is added mainly for the purpose of improving the adhesion between the substrate or the resist and the resist underlayer film forming composition, and preventing the resist from peeling particularly during development.
- Specific examples include chlorosilanes such as trimethylchlorosilane, dimethylvinylchlorosilane, methyldiphenylchlorosilane, chloromethyldimethylchlorosilane, trimethylmethoxysilane, dimethyldiethoxysilane, methyldimethoxysilane, dimethylvinylethoxysilane, diphenyldimethoxysilane, Alkoxysilanes such as enyltriethoxysilane, hexamethyldisilazane, N, N'-bis (trimethylsilyl) urea, silazanes such as dimethyltrimethylsilylamine, trimethylsilylimidazole, vinyltrichlorosilane, ⁇ -chloropropyltrimethoxy
- a surfactant can be blended in order to further improve the applicability to surface unevenness without occurrence of pinholes and setups.
- the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene alkyl ethers such as polyoxyethylene oleyl ether, polyoxyethylene octylphenol ether, polyoxyethylene nonyl Polyoxyethylene alkyl allyl ethers such as phenol ether, polyoxyethylene / polyoxypropylene block copolymers, sorbitan monolaurate, sorbitan monopalmitate, sorbitan monostearate, sorbitan monooleate, sorbitan trioleate, sorbitan tristearate Sorbitan fatty acid esters such as rate, polyoxyethylene sorbitan monolaurate, polyoxyethylene sol
- Nonionic surfactants such as polyoxyethylene sorbitan
- the compounding amount of these surfactants is usually 2.0% by mass or less, preferably 1.0% by mass or less, based on the total solid content of the resist underlayer film forming composition for lithography of the present invention.
- These surfactants may be added alone or in combination of two or more.
- the solvent for dissolving the resin, the crosslinking agent component, the crosslinking catalyst and the like are ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl.
- Ether diethylene glycol monoethyl ether, propylene glycol, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol propyl ether acetate, toluene, xylene, methyl ethyl ketone, cyclopentanone, Cyclohexanone, 2-hydroxypropion Ethyl, ethyl 2-hydroxy-2-methylpropionate, ethyl ethoxyacetate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, 3-ethoxypropionic acid Ethyl, methyl 3-ethoxypropionate, methyl pyruvate, ethyl pyruvate, ethyl acetate, but
- organic solvents are used alone or in combination of two or more.
- high boiling point solvents such as propylene glycol monobutyl ether and propylene glycol monobutyl ether acetate can be mixed and used.
- propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, ethyl lactate, butyl lactate, cyclohexanone and the like are preferable for improving the leveling property.
- the resist used in the present invention is a photoresist or an electron beam resist.
- the photoresist applied on the upper part of the resist underlayer film for lithography in the present invention either negative type or positive type can be used, and a positive type photoresist composed of a novolak resin and 1,2-naphthoquinonediazide sulfonic acid ester, depending on the acid.
- Chemically amplified photoresist comprising a binder having a group that decomposes to increase the alkali dissolution rate and a photoacid generator, a low molecular weight compound and photoacid that increases the alkali dissolution rate of the photoresist by decomposition with an alkali-soluble binder and acid
- Chemically amplified photoresist comprising a generator, comprising a binder having a group that decomposes with acid to increase the alkali dissolution rate, a low-molecular compound that decomposes with acid to increase the alkali dissolution rate of the photoresist, and a photoacid generator Chemically amplified photoresist with Si atoms in the skeleton
- a photoresist or the like which, for example, Rohm & Hearts Co., Ltd., and trade name APEX-E.
- an acid is generated by irradiation of a resin containing an Si-Si bond in the main chain and an aromatic ring at the terminal and an electron beam.
- examples include a composition comprising an acid generator, or a composition comprising a poly (p-hydroxystyrene) having a hydroxyl group substituted with an organic group containing N-carboxyamine and an acid generator that generates an acid upon irradiation with an electron beam. It is done.
- the acid generated from the acid generator by electron beam irradiation reacts with the N-carboxyaminoxy group of the polymer side chain, and the polymer side chain decomposes into a hydroxyl group and exhibits alkali solubility, thereby exhibiting alkali solubility.
- the acid generated from the acid generator by electron beam irradiation reacts with the N-carboxyaminoxy group of the polymer side chain, and the polymer side chain decomposes into a hydroxyl group and exhibits alkali solubility, thereby exhibiting alkali solubility.
- Acid generators that generate an acid upon irradiation with this electron beam are 1,1-bis [p-chlorophenyl] -2,2,2-trichloroethane, 1,1-bis [p-methoxyphenyl] -2,2,2 -Halogenated organic compounds such as trichloroethane, 1,1-bis [p-chlorophenyl] -2,2-dichloroethane, 2-chloro-6- (trichloromethyl) pyridine, triphenylsulfonium salts, diphenyliodonium salts, etc. Examples thereof include sulfonic acid esters such as onium salts, nitrobenzyl tosylate, and dinitrobenzyl tosylate.
- aqueous ammonia Inorganic amines such as ethylamine, primary amines such as n-propylamine, secondary amines such as diethylamine and di-n-butyl
- an appropriate amount of an alcohol such as isopropyl alcohol or a nonionic surfactant may be added to the alkaline aqueous solution.
- preferred developers are quaternary ammonium salts, more preferably tetramethylammonium hydroxide and choline.
- a spinner, a coater, etc. are suitably used on a substrate (for example, a transparent substrate such as a silicon / silicon dioxide coating, a glass substrate, an ITO substrate) used for manufacturing a precision integrated circuit device.
- a substrate for example, a transparent substrate such as a silicon / silicon dioxide coating, a glass substrate, an ITO substrate
- the resist underlayer film forming composition After applying the resist underlayer film forming composition by a simple coating method, it is baked and cured to form a coating type underlayer film.
- the thickness of the resist underlayer film is preferably 0.01 to 3.0 ⁇ m.
- the conditions for baking after coating are 80 to 350 ° C. and 0.5 to 120 minutes.
- a good resist pattern can be obtained by performing, developing, rinsing and drying. If necessary, post-irradiation heating (PEB: Post Exposure Bake) can be performed. Then, the resist underlayer film where the resist has been developed and removed by the above process is removed by dry etching, and a desired pattern can be formed on the substrate.
- PEB Post Exposure Bake
- the exposure light in the photoresist is actinic radiation such as near ultraviolet, far ultraviolet, or extreme ultraviolet (for example, EUV, wavelength 13.5 nm), for example, 248 nm (KrF laser light), 193 nm (ArF laser light), Light having a wavelength such as 157 nm (F 2 laser light) is used.
- the light irradiation can be used without particular limitation as long as it can generate an acid from a photoacid generator, and the exposure dose is 1 to 2000 mJ / cm 2 , or 10 to 1500 mJ / cm 2 , or 50. To 1000 mJ / cm 2 .
- the electron beam irradiation of an electron beam resist can be performed using an electron beam irradiation apparatus, for example.
- the semiconductor device can be manufactured through a step of etching the resist underlayer film with the formed resist pattern and a step of processing the semiconductor substrate with the patterned resist underlayer film.
- the resist underlayer film for lithography which has a selection ratio of dry etching rates close to that of resist, is selected as a resist underlayer film for such processes, and a lower dry etching rate than resist.
- resist underlayer film for lithography having a higher ratio and a resist underlayer film for lithography having a lower dry etching rate selection ratio than a semiconductor substrate.
- a resist underlayer film can be provided with an antireflection ability, and can also have a function of a conventional antireflection film.
- a process of making the resist pattern and the resist underlayer film narrower than the pattern width at the time of developing the resist during dry etching of the resist underlayer film has begun to be used.
- a resist underlayer film having a selectivity of a dry etching rate close to that of the resist has been required as a resist underlayer film for such a process.
- such a resist underlayer film can be provided with an antireflection ability, and can also have a function of a conventional antireflection film.
- the substrate after forming the resist underlayer film of the present invention on a substrate, directly or optionally forming one to several layers of coating material on the resist underlayer film, A resist can be applied. As a result, the pattern width of the resist becomes narrow, and even when the resist is thinly coated to prevent pattern collapse, the substrate can be processed by selecting an appropriate etching gas.
- a step of forming a resist underlayer film on a semiconductor substrate with a resist underlayer film forming composition, and a hard mask made of a coating material containing a silicon component or the like or a hard mask (for example, silicon nitride oxide) is formed thereon
- a semiconductor device can be manufactured through a step of etching the resist underlayer film with an oxygen-based gas or a hydrogen-based gas with a hard mask and a step of processing a semiconductor substrate with a halogen-based gas with a patterned resist underlayer film.
- the resist underlayer film forming composition for lithography of the present invention has a light absorption site incorporated into the skeleton, so there is no diffused material in the photoresist during heating and drying. Moreover, since the light absorption site has a sufficiently large light absorption performance, the effect of preventing reflected light is high.
- composition for forming a resist underlayer film for lithography of the present invention has high thermal stability, can prevent contamination of the upper layer film by decomposition products during baking, and can provide a margin for the temperature margin of the baking process. is there.
- the resist underlayer film forming composition for lithography of the present invention has a function of preventing reflection of light depending on process conditions, and further prevents the interaction between the substrate and the photoresist or the material used for the photoresist or the photo resist.
- the film can be used as a film having a function of preventing an adverse effect on a substrate of a substance generated upon exposure of the resist.
- the present invention provides the following formula (5): (Wherein Q 3 represents an isopropylidene group (—C (CH 3 ) 2 —), R 14 represents a carbon atom having an alkyl group having 2 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms) R 2 represents an alkyl group having 2 to 10 carbon atoms, R 15 represents a hydrogen atom or a methyl group, and R 13 represents an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 40 carbon atoms.
- n17 is an integer of 1 ⁇ n17 ⁇ 3
- n18 is an integer of 1 ⁇ n18 ⁇ 4
- n19 is an integer of 0 ⁇ n19 ⁇ 3
- n20 is an integer of 0 ⁇ n20 ⁇ 3
- Synthesis example 1 In a 100 mL eggplant flask, TMOM-BP (20.00 g, 0.055 mol, manufactured by Honshu Chemical Industry Co., Ltd., formula (4-23)) and PGME (propylene glycol monomethyl ether, 80.00 g) were charged and stirred. The temperature was raised until dissolution was confirmed, and dissolution was started to initiate polymerization. After 24 hours, the mixture was allowed to cool to 30 ° C., and then the TMOM-BP-PGME in the PGME solution (formula (3-1), formula (3-2), formula (3 The compound represented by -3) was mixed. As a result of identifying the abundance ratio of the four substitution products of TMOM-BP-PGME by GPC, it was found to be present at 34 mol% in the whole TMOM-BP-PGME.
- Synthesis example 2 In a 200 mL eggplant flask, TMOM-BP (5.00 g, 0.014 mol, manufactured by Honshu Chemical Industry Co., Ltd., formula (4-23)), 15 JWET (20.00 g, trade name Amberlist) washed as an ion exchange resin for a catalyst , Manufactured by Dow Chemical Co., Ltd.) and PGME (propylene glycol monomethyl ether, 75.00 g) were stirred and heated until the reflux was confirmed and dissolved to start polymerization. After cooling to 60 ° C.
- TMOM-BP-PGME2 target material
- TMOM-BP-PGME2 target material
- Synthesis example 3 In a 200 mL four-necked flask, TMOM-BP (3.00 g, 0.008 mol, manufactured by Honshu Chemical Industry Co., Ltd., formula (4-23)), 15 JWET (12.00 g, trade name) washed as an ion exchange resin for a catalyst Amberlist, manufactured by Dow Chemical Co., Ltd. was added, butanol (60.00 g, manufactured by Kanto Chemical Co., Inc.) was added and stirred, and polymerization was started at 100 ° C. After cooling to 30 ° C. after 48 hours, 15 JWET was filtered, concentrated and dried under reduced pressure at 30 ° C.
- TMOM-BP 3.00 g, 0.008 mol, manufactured by Honshu Chemical Industry Co., Ltd., formula (4-23)
- 15 JWET (12.00 g, trade name) washed as an ion exchange resin for a catalyst Amberlist, manufactured by Dow Chemical Co., Ltd. was added, butanol (60.00 g, manufactured by Kanto
- TBOM-BP-BU a compound corresponding to the formula (3-8)
- the compound represented by formula (3-5), formula (3-6), and formula (3-7) was mixed.
- the structure was analyzed by 1 H-NMR, and it was confirmed that the target compound was obtained. It was also confirmed by HPLC that the ratio of TBOM-BP-BU tetrasubstituted compounds was 85 mol% in the entire TBOM-BP-BU.
- the NMR spectrum of the tetrasubstituted TBOM-BP-BU showed the following characteristic absorption (FIG. 1).
- Synthesis example 4 In a 200 mL four-necked flask, TM-BIP-A (3.00 g, 0.009 mol, manufactured by Honshu Chemical Industry Co., Ltd., formula (4-24)), 15 JWET (12.00 g, Trade name Amberlist, manufactured by Dow Chemical Co., Ltd. was added, butanol (60.00 g, manufactured by Kanto Chemical Co., Inc.) was added and stirred, and polymerization was started at 100 ° C. After cooling to 30 ° C. after 3.5 hours, 15 JWET was filtered, concentrated and dried at 30 ° C.
- TBOM-BIP-A 3.0 g.
- the structure was analyzed by 1 H-NMR, and it was confirmed that the target compound was obtained. Further, it was confirmed by HPLC that the abundance ratio of the 4-substituent of TBOM-BIP-A was 95 mol% in the entire TBOM-BIP-A.
- the NMR spectrum of the 4-substituted product of TBOM-BIP-A showed the following characteristic absorption (FIG. 2).
- Synthesis example 5 In a 200 mL four-necked flask, TM-BIP-A (4.00 g, 0.011 mol, manufactured by Honshu Chemical Industry Co., Ltd., formula (4-24)), 15 JWET (16.00 g, Trade name Amberlist, manufactured by Dow Chemical Co., Ltd.) was added, 1-propanol (80.00 g, manufactured by Kanto Chemical Co., Inc.) was added and stirred, and polymerization was started at the reflux temperature. After cooling to 30 ° C. after 4 hours, 15 JWET was filtered, concentrated and dried under reduced pressure at 30 ° C.
- TPOM-BIP-A The compounds represented by the formulas (3-14) and (3-15) were mixed, hereinafter abbreviated as TPOM-BIP-A) to obtain 5.0 g.
- the structure was analyzed by 1 H-NMR, and it was confirmed that the target compound was obtained. Further, it was confirmed by HPLC that the ratio of the 4-substitution of TPOM-BIP-A was 94 mol% in the entire TPOM-BIP-A.
- the NMR spectrum of the 4-substituted TPOM-BIP-A showed the following characteristic absorption (FIG. 3).
- TEOM-BIP-A the compound of formula (3- 17), compounds of formula (3-18) and formula (3-19) were mixed (hereinafter abbreviated as TEOM-BIP-A) to obtain 4.2 g.
- the structure was analyzed by 1 H-NMR, and it was confirmed that the target compound was obtained. Further, it was confirmed by HPLC that the ratio of the tetrasubstituted TEOM-BIP-A was 95 mol% in the entire TEOM-BIP-A.
- the NMR spectrum of the tetrasubstituted TEOM-BIP-A showed the following characteristic absorption (FIG. 4).
- Synthesis example 7 In a 200 mL four-necked flask, TM-BIP-A (4.00 g, 0.011 mol, manufactured by Honshu Chemical Industry Co., Ltd., formula (4-24)), 15 JWET (16.00 g, Trade name Amberlist, manufactured by Dow Chemical Co., Ltd.) was added, 2-methyl-1-propanol (80.00 g, manufactured by Kanto Chemical Co., Inc.) was added and stirred, and polymerization was started at 100 ° C. After cooling to 30 ° C. after 4 hours, 15 JWET was filtered, concentrated and dried under reduced pressure at 30 ° C.
- TIBOM-BIP-A The compounds represented by formula (3-22) and formula (3-23) were mixed, hereinafter abbreviated as TIBOM-BIP-A) to obtain 5.8 g.
- the structure was analyzed by 1 H-NMR, and it was confirmed that the target compound was obtained. Further, it was confirmed by HPLC that the ratio of the 4-substitution of TIBOM-BIP-A was 95 mol% in the entire TIBOM-BIP-A.
- the NMR spectrum of the 4-substitution of TIBOM-BIP-A showed the following characteristic absorption (FIG. 5).
- Synthesis example 8 In a 200 mL four-necked flask, TM-BIP-A (4.00 g, 0.011 mol, manufactured by Honshu Chemical Industry Co., Ltd., formula (4-24)), 15 JWET (16.00 g, The product name Amberlist, manufactured by Dow Chemical Co., Ltd.) was added, 2-methoxyethanol (80.00 g, manufactured by Kanto Chemical Co., Inc.) was added and stirred, and polymerization was started at 100 ° C. After cooling to 30 ° C. after 1 hour, 15 JWET was filtered, concentrated and dried at 30 ° C.
- the compounds represented by the formulas (3-26) and (3-27) were mixed (hereinafter abbreviated as EGME-BIP-A) to obtain 5.3 g.
- the structure was analyzed by 1 H-NMR, and it was confirmed that the target compound was obtained. Further, it was confirmed by HPLC that the ratio of the 4-substituent of EGME-BIP-A was 94 mol% in the entire EGME-BIP-A.
- the NMR spectrum of the 4-substituted product of EGME-BIP-A showed the following characteristic absorption (FIG. 6).
- the compound represented by the formula (3-30) and the formula (3-31) was mixed (hereinafter abbreviated as EGEE-BIP-A) to obtain 3.0 g.
- the structure was analyzed by 1 H-NMR, and it was confirmed that the target compound was obtained. Further, it was confirmed by HPLC that the ratio of the 4-substituted product of EGEE-BIP-A was 92 mol% in the entire EGEE-BIP-A.
- the NMR spectrum of the tetrasubstituted EGEE-BIP-A showed the following characteristic absorption (FIG. 7).
- the compound represented by the formula (3-34) and the formula (3-35) was mixed (hereinafter abbreviated as PGME-BIP-A) to obtain 3.0 g.
- the structure was analyzed by 1 H-NMR, and it was confirmed that the target compound was obtained. Further, it was confirmed by HPLC that the ratio of the 4-substituted product of PGME-BIP-A was 74 mol% in the entire PGME-BIP-A.
- the NMR spectrum of the 4-substituted product of PGME-BIP-A showed the following characteristic absorption (FIG. 8).
- EGIPE-BIP-A The compound represented by the formula (3-37), the formula (3-38), and the formula (3-39) was mixed with the compound as the center (hereinafter abbreviated as EGIPE-BIP-A) to obtain 3.0 g.
- the structure was analyzed by 1 H-NMR, and it was confirmed that the target compound was obtained. Further, it was confirmed by HPLC that the ratio of the 4-substituted product of EGIPE-BIP-A was 84 mol% in the whole EGIPE-BIP-A.
- the NMR spectrum of the 4-substituted product of EGIPE-BIP-A showed the following characteristic absorption (FIG. 9).
- pNPNA-NA target polymer 11 0.6 g was obtained.
- the weight average molecular weight Mw measured in terms of polystyrene by GPC of pNPNA-NA was 1400, and the polydispersity Mw / Mn was 1.62.
- Example 1 To 0.51 g of the pNPNA-NA resin obtained in Synthesis Example 12, 0.10 g of TMOM-BP-PGME of Synthesis Example 1 as a crosslinking agent, 0.02 g of pPTS (pyridinium paratoluenesulfonate) as a catalyst, and Mega as a surfactant Facque R-30N (Dainippon Ink Chemical Co., Ltd., trade name) 0.001 g was mixed and dissolved in 7.16 g of PGMEA (propylene glycol monomethyl ether acetate), 1.52 g of PGME and 2.39 g of cyclohexanone. Solution.
- PGMEA propylene glycol monomethyl ether acetate
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 2 0.51 g of the pNPNA-NA resin obtained in Synthesis Example 12, 0.10 g of TMOM-BP-PGME2 of Synthesis Example 2 as a cross-linking agent, 0.02 g of pPTS as a catalyst, and MegaFac R-30N as a surfactant (Dainippon) Ink Chemical Co., Ltd. (trade name) 0.001 g was mixed and dissolved in 7.16 g of PGMEA (propylene glycol monomethyl ether acetate), 1.52 g of PGME and 2.39 g of cyclohexanone to obtain a solution.
- PGMEA propylene glycol monomethyl ether acetate
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 3 0.51 g of the pNPNA-NA resin obtained in Synthesis Example 12, 0.10 g of TBOM-BP-BU of Synthesis Example 3 as a crosslinking agent, 0.02 g of pPTS as a catalyst, and MegaFac R-30N as a surfactant (Dainippon) Ink Chemical Co., Ltd. (trade name) 0.001 g was mixed and dissolved in 7.16 g of PGMEA (propylene glycol monomethyl ether acetate), 1.52 g of PGME and 2.39 g of cyclohexanone to obtain a solution.
- PGMEA propylene glycol monomethyl ether acetate
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 4 0.51 g of the pNPNA-NA resin obtained in Synthesis Example 12, 0.10 g of TBOM-BIP-A of Synthesis Example 4 as a crosslinking agent, 0.02 g of pPTS as a catalyst, and MegaFac R-30N as a surfactant (Dainippon) Ink Chemical Co., Ltd. (trade name) 0.001 g was mixed and dissolved in 7.16 g of PGMEA (propylene glycol monomethyl ether acetate), 1.52 g of PGME and 2.39 g of cyclohexanone to obtain a solution.
- PGMEA propylene glycol monomethyl ether acetate
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 5 0.51 g of the pNPNA-NA resin obtained in Synthesis Example 12, 0.10 g of TPOM-BIP-A of Synthesis Example 5 as a cross-linking agent, 0.02 g of pPTS as a catalyst, and MegaFac R-30N as a surfactant (Dainippon) Ink Chemical Co., Ltd. (trade name) 0.001 g was mixed and dissolved in 7.16 g of PGMEA (propylene glycol monomethyl ether acetate), 1.52 g of PGME and 2.39 g of cyclohexanone to obtain a solution.
- PGMEA propylene glycol monomethyl ether acetate
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 6 0.51 g of the pNPNA-NA resin obtained in Synthesis Example 12, 0.10 g of TEOM-BIP-A of Synthesis Example 6 as a crosslinking agent, 0.02 g of pPTS as a catalyst, and MegaFac R-30N as a surfactant (Dainippon) Ink Chemical Co., Ltd. (trade name) 0.001 g was mixed and dissolved in 7.16 g of PGMEA (propylene glycol monomethyl ether acetate), 1.52 g of PGME and 2.39 g of cyclohexanone to obtain a solution.
- PGMEA propylene glycol monomethyl ether acetate
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 7 0.51 g of the pNPNA-NA resin obtained in Synthesis Example 12, 0.10 g of TIBOM-BIP-A of Synthesis Example 7 as a crosslinking agent, 0.02 g of pPTS as a catalyst, and MegaFac R-30N as a surfactant (Dainippon) Ink Chemical Co., Ltd. (trade name) 0.001 g was mixed and dissolved in 7.16 g of PGMEA (propylene glycol monomethyl ether acetate), 1.52 g of PGME and 2.39 g of cyclohexanone to obtain a solution.
- PGMEA propylene glycol monomethyl ether acetate
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 8 0.51 g of the pNPNA-NA resin obtained in Synthesis Example 12, 0.10 g of EGME-BIP-A of Synthesis Example 8 as a crosslinking agent, 0.02 g of pPTS as a catalyst, and MegaFac R-30N as a surfactant (Dainippon) Ink Chemical Co., Ltd. (trade name) 0.001 g was mixed and dissolved in 7.16 g of PGMEA (propylene glycol monomethyl ether acetate), 1.52 g of PGME and 2.39 g of cyclohexanone to obtain a solution.
- PGMEA propylene glycol monomethyl ether acetate
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 9 0.51 g of the pNPNA-NA resin obtained in Synthesis Example 12, 0.10 g of EGEE-BIP-A of Synthesis Example 9 as a cross-linking agent, 0.02 g of pPTS as a catalyst, and MegaFac R-30N as a surfactant (Dainippon) Ink Chemical Co., Ltd. (trade name) 0.001 g was mixed and dissolved in 7.16 g of PGMEA (propylene glycol monomethyl ether acetate), 1.52 g of PGME and 2.39 g of cyclohexanone to obtain a solution.
- PGMEA propylene glycol monomethyl ether acetate
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 10 To 0.51 g of the pNPNA-NA resin obtained in Synthesis Example 12, 0.10 g of PGME-BIP-A of Synthesis Example 10 as a cross-linking agent, 0.02 g of pPTS as a catalyst, and Megafac R-30N as a surfactant (Dainippon) Ink Chemical Co., Ltd. (trade name) 0.001 g was mixed and dissolved in 7.16 g of PGMEA (propylene glycol monomethyl ether acetate), 1.52 g of PGME and 2.39 g of cyclohexanone to obtain a solution.
- PGMEA propylene glycol monomethyl ether acetate
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- Example 11 0.51 g of the pNPNA-NA resin obtained in Synthesis Example 12, 0.10 g of EGIPE-BIP-A of Synthesis Example 11 as a cross-linking agent, 0.02 g of pPTS as a catalyst, and MegaFac R-30N as a surfactant (Dainippon) Ink Chemical Co., Ltd. (trade name) 0.001 g was mixed and dissolved in 7.16 g of PGMEA (propylene glycol monomethyl ether acetate), 1.52 g of PGME and 2.39 g of cyclohexanone to obtain a solution.
- PGMEA propylene glycol monomethyl ether acetate
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- the solution is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- a polyethylene microfilter having a pore size of 0.10 ⁇ m is filtered using a polyethylene microfilter having a pore size of 0.10 ⁇ m, and further filtered using a polyethylene microfilter having a pore size of 0.05 ⁇ m, so that the resist underlayer film forming composition solution used in the lithography process using a multilayer film is used.
- the amount of sublimation was measured using a sublimation amount measuring device described in International Publication No. 2007/111147 pamphlet.
- the resist underlayer film forming composition prepared in Examples 1 to 11 and Comparative Examples 1 to 4 was applied to a silicon wafer substrate having a diameter of 4 inches with a spin coater so as to have a film thickness of 100 nm. .
- the wafer coated with the resist underlayer film is set in the sublimation amount measuring apparatus in which the hot plate is integrated, baked for 120 seconds, and the sublimation is placed on a QCM (Quartz Crystal Microbalance) sensor, that is, a crystal resonator on which an electrode is formed. I collected it.
- the QCM sensor can measure a small amount of mass change by utilizing the property that when a sublimate adheres to the surface (electrode) of the crystal unit, the frequency of the crystal unit changes (decreases) according to the mass. .
- the detailed measurement procedure is as follows.
- the hot plate of the sublimation amount measuring apparatus was heated to the measurement temperature shown in Table 1, the pump flow rate was set to 1 m 3 / s, and the first 60 seconds was left to stabilize the apparatus.
- the wafer coated with the resist underlayer film was quickly placed on the hot plate from the slide opening, and the sublimates were collected from 60 seconds to 180 seconds (120 seconds).
- the flow attachment (detection part) that connects the QCM sensor and the collection funnel part of the sublimation quantity measuring device is used without a nozzle, so that the chamber with a distance of 30 mm from the sensor (quartz crystal unit) is used.
- the airflow flows from the unit flow path (caliber: 32 mm) without being restricted.
- the QCM sensor uses a material mainly composed of silicon and aluminum (AlSi) as an electrode, the diameter of the crystal unit (sensor diameter) is 14 mm, the electrode diameter on the surface of the crystal unit is 5 mm, and the resonance frequency is 9 MHz.
- the thing of was used.
- the obtained frequency change was converted into grams from the eigenvalue of the quartz crystal used for the measurement, and the relationship between the amount of sublimation of one wafer coated with the resist underlayer film and the passage of time was clarified.
- the first 60 seconds is a time zone in which the wafer is left to stabilize the apparatus (no wafer is set), and the measured values from the time of 60 seconds to 180 seconds when the wafer is placed on the hot plate are the wafers.
- Table 1 shows the amount of sublimation of the resist underlayer film determined from the apparatus as the sublimation amount ratio.
- the amount of sublimation was defined as good if it was less than 2000 ng as the upper limit and bad if it was more.
- the thing of 2000 ng or less is represented by ⁇ , and the above is represented by ⁇ .
- the resist underlayer film forming composition solutions prepared in Examples 1 to 11 and Comparative Examples 1 to 4 were each applied onto a silicon wafer using a spin coater.
- the resist underlayer film (film thickness: 0.25 ⁇ m) was formed by baking at 400 ° C. for 2 minutes on a hot plate.
- This resist underlayer film was immersed in a solvent used for the resist, for example, ethyl lactate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, and cyclohexanone, and it was confirmed that the resist underlayer film was insoluble in the solvent.
- the resist underlayer film forming composition used in the lithography process using the crosslinking agent of the present invention is different from the conventional material in which the generation of sublimates is kept low and the embedding in the hole pattern is difficult to achieve at the same time. It is possible to provide a resist underlayer film having both characteristics.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Structural Engineering (AREA)
- Architecture (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Computer Hardware Design (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Power Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Materials For Photolithography (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Abstract
Description
本発明は昇華物の発生が少なく、ホールパターンを有する基板に塗布した時に埋め込み性の良好なレジスト下層膜形成組成物を提供する。
(式中、Q1は単結合又はm1価の有機基を示し、R1及びR4はそれぞれ炭素原子数2乃至10のアルキル基、又は炭素原子数1乃至10のアルコキシ基を有する炭素原子数2乃至10のアルキル基を示し、R2及びR5はそれぞれ水素原子又はメチル基を示し、R3及びR6はそれぞれ炭素原子数1乃至10のアルキル基、又は炭素原子数6乃至40のアリール基を示す。
n1は1≦n1≦3の整数、n2は2≦n2≦5の整数、n3は0≦n3≦3の整数、n4は0≦n4≦3の整数、3≦(n1+n2+n3+n4)≦6の整数を示す。
n5は1≦n5≦3の整数、n6は1≦n6≦4の整数、n7は0≦n7≦3の整数、n8は0≦n8≦3の整数、2≦(n5+n6+n7+n8)≦5の整数を示す。m1は2乃至10の整数を示す。)で示される架橋性化合物を含むレジスト下層膜形成組成物、
第2観点として、Q1が単結合、又は炭素原子数1乃至10の鎖状炭化水素基、炭素原子数6乃至40の芳香族基、若しくはそれらの組み合わせから選ばれるm1価の有機基である第1観点に記載のレジスト下層膜形成組成物、
第3観点として、上記式(1)又は式(2)で示される架橋性化合物が、下記式(3)又は式(4)で示される化合物と、ヒドロキシル基含有エーテル化合物又は炭素原子数2乃至10のアルコールとの反応によって得られるものである第1観点又は第2観点に記載のレジスト下層膜形成組成物、
(式中、Q2は単結合又はm2価の有機基を示す。R8、R9、R11及びR12はそれぞれ水素原子又はメチル基を示し、R7及びR10はそれぞれ炭素原子数1乃至10のアルキル基、又は炭素原子数6乃至40のアリール基を示す。
n9は1≦n9≦3の整数、n10は2≦n10≦5の整数、n11は0≦n11≦3の整数、n12は0≦n12≦3の整数、3≦(n9+n10+n11+n12)≦6の整数を示す。
n13は1≦n13≦3の整数、n14は1≦n14≦4の整数、n15は0≦n15≦3の整数、n16は0≦n16≦3の整数、2≦(n13+n14+n15+n16)≦5の整数を示す。m2は2乃至10の整数を示す。)、
第4観点として、上記式(3)又は式(4)で示される化合物と、ヒドロキシル基含有エーテル化合物又は炭素原子数2乃至10のアルコールとの反応が酸触媒の存在下で行われる第3観点に記載のレジスト下層膜形成組成物、
第5観点として、酸触媒が触媒用イオン交換樹脂である第4観点に記載のレジスト下層膜形成組成物、
第6観点として、ヒドロキシル基含有エーテル化合物がプロピレングリコールモノメチルエーテル又はプロピレングリコールモノエチルエーテルである第3観点乃至第5観点のいずれか一つに記載のレジスト下層膜形成組成物、
第7観点として、炭素原子数2乃至10のアルコールが、エタノール、1-プロパノール、2-メチル-1-プロパノール、ブタノール、2-メトキシエタノール又は2-エトキシエタノールである第3観点乃至第5観点のいずれか一つに記載のレジスト下層膜形成組成物、
第8観点として、樹脂がノボラック樹脂である第1観点乃至第7観点のいずれか一つに記載のレジスト下層膜形成組成物、
第9観点として、更に架橋剤を含む第1観点乃至第8観点のいずれか一つに記載のレジスト下層膜形成組成物、
第10観点として、更に酸及び/又は酸発生剤を含む第1観点乃至第9観点のいずれか一つに記載のレジスト下層膜形成組成物、
第11観点として、第1観点乃至第10観点のいずれか一つに記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成することによって得られるレジスト下層膜、
第12観点として、第1観点乃至第10観点のいずれか一つに記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成してレジスト下層膜を形成する工程を含む半導体の製造に用いるレジストパターンの形成方法、
第13観点として、半導体基板上に第1観点乃至第10観点のいずれか一つに記載のレジスト下層膜形成組成物によりレジスト下層膜を形成する工程、その上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、形成されたレジストパターンにより該レジスト下層膜をエッチングする工程、及びパターン化されたレジスト下層膜により半導体基板を加工する工程を含む半導体装置の製造方法、
第14観点として、半導体基板上に第1観点乃至第10観点のいずれか一つに記載のレジスト下層膜形成組成物によりレジスト下層膜を形成する工程、その上にハードマスクを形成する工程、更にその上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、形成されたレジストパターンによりハードマスクをエッチングする工程、パターン化されたハードマスクにより該レジスト下層膜をエッチングする工程、及びパターン化されたレジスト下層膜により半導体基板を加工する工程を含む半導体装置の製造方法、
第15観点として、ハードマスクが無機物の塗布又は無機物の蒸着により形成されたものである第14観点に記載の製造方法、及び
第16観点として、下記式(5):
(式中、Q3はイソプロピリデン基を示し、R14は炭素原子数2乃至10のアルキル基、又は炭素原子数1乃至10のアルコキシ基を有する炭素原子数2乃至10のアルキル基を示し、R15は水素原子又はメチル基を示し、R13は炭素原子数1乃至10のアルキル基、又は炭素原子数6乃至40のアリール基を示す。
n17は1≦n17≦3の整数、n18は1≦n18≦4の整数、n19は0≦n19≦3の整数、n20は0≦n20≦3の整数、2≦(n17+n18+n19+n20)≦5の整数を示す。)で示される化合物である。
従って、本発明の組成物は上記置換された架橋性化合物を用いることによってコーティング欠陥の発生を抑制することができる。
また、固形分中に式(1)又は式(2)で示される架橋性化合物を0.01乃至50質量%、又は0.01乃至40質量%、又は0.1乃至30質量%の割合で含有することができる。
本発明に用いられるポリマーは、重量平均分子量が600乃至1000000、又は600乃至200000である。
n1は1≦n1≦3の整数、n2は2≦n2≦5の整数、n3は0≦n3≦3の整数、n4は0≦n4≦3の整数、3≦(n1+n2+n3+n4)≦6の整数を示す。
n5は1≦n5≦3の整数、n6は1≦n6≦4の整数、n7は0≦n7≦3の整数、n8は0≦n8≦3の整数、2≦(n5+n6+n7+n8)≦5の整数を示す。m1は2乃至10の整数を示す。
上記Q1は単結合であるか、又は炭素原子数1乃至10の鎖状炭化水素基、炭素原子数6乃至40の芳香族基、又はそれらの組み合わせから選ばれるm1価の有機基とすることができる。ここで、鎖状炭化水素基は下記アルキル基を挙げることができる。芳香族基は下記アリール基を挙げることができる。
また、炭素原子数1乃至10のアルキル基は上記炭素原子数2乃至10のアルキル基に更にメチル基が例示される。
炭素原子数6乃至40のアリール基としてはフェニル基、ナフチル基、アントリル基等が挙げられる。
式(3)又は式(4)で示される化合物1モルに、ヒドロキシル基含有エーテル化合物又は炭素原子数2乃至10のアルコールが1モルの割合で置換した式(1)又は式(2)で示される化合物を1置換体、同様に2モル置換した式(1)又は式(2)で示される化合物を2置換体、同様に3モル置換した式(1)又は式(2)で示される化合物を3置換体、同様に4モル置換した式(1)又は式(2)で示される化合物を4置換体とする。
R8、R9、R11及びR12はそれぞれ水素原子又はメチル基を示し、R7及びR10はそれぞれ炭素原子数1乃至10のアルキル基、又は炭素原子数6乃至40のアリール基を示す。
n9は1≦n9≦3の整数、n10は2≦n10≦5の整数、n11は0≦n11≦3の整数、n12は0≦n12≦3の整数、3≦(n9+n10+n11+n12)≦6の整数を示す。
n13は1≦n13≦3の整数、n14は1≦n14≦4の整数、n15は0≦n15≦3の整数、n16は0≦n16≦3の整数、2≦(n13+n14+n15+n16)≦5の整数を示す。m2は2乃至10の整数を示す。
しかし、反応系に未反応の酸を残存させないために触媒用イオン交換樹脂を用いることができる。触媒用イオン交換樹脂は例えば、スルホン酸型の強酸型イオン交換樹脂を用いることができる。
上記ヒドロキシル基含有エーテル化合物はプロピレングリコールモノメチルエーテル、又はプロピレングリコールモノエチルエーテルが挙げられる。
また、炭素原子数2乃至10のアルコールはエタノール、1-プロパノール、2-メチル-1-プロパノール、ブタノール、2-メトキシエタノール又は2-エトキシエタノールが挙げられる。
これら架橋形成基を有する樹脂はアクリル樹脂、ノボラック樹脂が挙げられるが、ノボラック樹脂が好ましく用いることができる。
また、アルデヒドとしてはホルムアルデヒド、パラホルムアルデヒド、アセトアルデヒド、プロピルアルデヒド、ブチルアルデヒド、イソブチルアルデヒド、バレルアルデヒド、カプロンアルデヒド、2-メチルブチルアルデヒド、ヘキシルアルデヒド、ウンデカンアルデヒド、7-メトキシ-3、7-ジメチルオクチルアルデヒド、シクロヘキサンアルデヒド、3-メチル-2-ブチルアルデヒド、グリオキザール、マロンアルデヒド、スクシンアルデヒド、グルタルアルデヒド、アジピンアルデヒド、等の飽和脂肪族アルデヒド類、アクロレイン、メタクロレイン等の不飽和脂肪族アルデヒド類、フルフラール、ピリジンアルデヒド等のヘテロ環式アルデヒド類、ベンズアルデヒド、ナフチルアルデヒド、アントリルアルデヒド、フェナントリルアルデヒド、サリチルアルデヒド、フェニルアセトアルデヒド、3-フェニルプロピオンアルデヒド、トリルアルデヒド、(N,N-ジメチルアミノ)ベンズアルデヒド、アセトキシベンズアルデヒド、1-ピレンカルボキシアルデヒド等の芳香族アルデヒド類等が挙げられる。
また、ケトンとしては、ジアリールケトン類であり、例えばジフェニルケトン、フェニルナフチルケトン、ジナフチルケトン、フェニルトリルケトン、ジトリルケトン、9-フルオレノン等が挙げられる。
縮合時の反応温度は通常40℃乃至200℃である。反応時間は反応温度によって種々選択されるが、通常30分乃至50時間程度である。
また、更に式(1)、式(2)で示される架橋剤化合物以外の架橋剤を含有することができる。それらの架橋剤としては、メラミン系、置換尿素系、またはそれらのポリマー系等が挙げられる。好ましくは、少なくとも2個の架橋形成置換基を有する架橋剤であり、メトキシメチル化グリコールウリル、ブトキシメチル化グリコールウリル、メトキシメチル化メラミン、ブトキシメチル化メラミン、メトキシメチル化ベンゾグワナミン、ブトキシメチル化ベンゾグワナミン、メトキシメチル化尿素、ブトキシメチル化尿素、メトキシメチル化チオ尿素、またはメトキシメチル化チオ尿素等の化合物である。また、これらの化合物の縮合体も使用することができる。
さらに、プロピレングリコールモノブチルエーテル、プロピレングリコールモノブチルエーテルアセテート等の高沸点溶剤を混合して使用することができる。これらの溶剤の中でプロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、乳酸エチル、乳酸ブチル、及びシクロヘキサノン等がレベリング性の向上に対して好ましい。
本発明に用いられるレジストとはフォトレジストや電子線レジストである。
また電子線レジストの電子線照射は、例えば電子線照射装置を用い照射することができる。
さらにまた、本発明は下記式(5):
(式中、Q3はイソプロピリデン基(-C(CH3)2-)を示し、R14は炭素原子数2乃至10のアルキル基、又は炭素原子数1乃至10のアルコキシ基を有する炭素原子数2乃至10のアルキル基を示し、R15は水素原子又はメチル基を示し、R13は炭素原子数1乃至10のアルキル基、又は炭素原子数6乃至40のアリール基を示す。
n17は1≦n17≦3の整数、n18は1≦n18≦4の整数、n19は0≦n19≦3の整数、n20は0≦n20≦3の整数、2≦(n17+n18+n19+n20)≦5の整数を示す。)で示される新規な化合物にも関する。
上記アルキル基、アルコキシ基、アリール基は上述の例示を示すことができる。
100mLナスフラスコにTMOM-BP(20.00g、0.055mol、本州化学工業(株)製、式(4-23))とPGME(プロピレングリコールモノメチルエーテル、80.00g)を仕込み撹拌し、リフラックスが確認されるまで昇温し溶解させ重合を開始した。24時間後30℃まで放冷後、PGME溶液中のTMOM-BP-PGME(式(3-4)に相当する化合物を中心に式(3-1)、式(3-2)、式(3-3)で示される化合物が混合されていた。)を得た。TMOM-BP-PGMEの4置換体の存在比率の同定をGPCで行った結果、TMOM-BP-PGME全体中に34モル%で存在していた。
200mLナスフラスコにTMOM-BP(5.00g、0.014mol、本州化学工業(株)製、式(4-23))、触媒用イオン交換樹脂として洗浄済みの15JWET(20.00g、商品名Amberlist、ダウケミカル社製)、PGME(プロピレングリコールモノメチルエーテル、75.00g)を仕込み撹拌し、リフラックスが確認されるまで昇温し溶解させ重合を開始した。48時間後60℃まで放冷後、濾過を行って15JWETを除去し、得られた沈殿物をろ過し、得られた目的の材料(式(3-4)に相当する化合物を中心に式(3-1)、式(3-2)、式(3-3)で示される化合物が混合されていた。以下TMOM-BP-PGME2と略す)を得た。
TMOM-BP-PGME2の4置換体の存在比率の同定をGPCで行った結果、TMOM-BP-PGME2全体中に68モル%で存在していた。
200mL四口フラスコにTMOM-BP(3.00g、0.008mol、本州化学工業(株)製、式(4-23))、触媒用イオン交換樹脂として洗浄済みの15JWET(12.00g、商品名Amberlist、ダウ・ケミカル社製)を加え、ブタノール(60.00g、関東化学(株)製)を仕込み撹拌し、100℃で重合を開始した。48時間後30℃まで放冷後、15JWETをろ過し30℃減圧下で2時間濃縮、乾燥させ、目的とする材料(以下TBOM-BP-BUと略す、式(3-8)に相当する化合物を中心に式(3-5)、式(3-6)、式(3-7)で示される化合物が混合されていた。)2.9gを得た。
1H-NMRにより構造解析を行い、目的の化合物が得られていることを確認した。また、HPLCによりTBOM-BP-BUの4置換体の存在比率が、TBOM-BP-BU全体中に85モル%であることを確認した。
TBOM-BP-BUの4置換体のNMRスペクトルは以下の特性吸収を示した(図1)。
1H-NMR(500MHz、DMSO-d6):0.89ppm(t、12H)、1.36ppm(m、8H)、1.54ppm(m、8H)、3.49(t、8H)、4.54(s、8H)、7.34(s、4H)、8.50(s、2H)。
200mL四口フラスコにTM-BIP-A(3.00g、0.009mol、本州化学工業(株)製、式(4-24))、触媒用イオン交換樹脂として洗浄済みの15JWET(12.00g、商品名Amberlist、ダウ・ケミカル社製)を加え、ブタノール(60.00g、関東化学(株)製)を仕込み撹拌し、100℃で重合を開始した。3.5時間後30℃まで放冷後、15JWETをろ過し30℃減圧下で2時間濃縮、乾燥させ、目的とする材料(式(3-12)に相当する化合物を中心に式(3-9)、式(3-10)、式(3-11)で示される化合物が混合されていた。以下TBOM-BIP-Aと略す)3.0gを得た。
1H-NMRにより構造解析を行い、目的の化合物が得られていることを確認した。また、HPLCによりTBOM-BIP―Aの4置換体の存在比率が、TBOM-BIP―A全体中に95モル%であることを確認した。
TBOM-BIP―Aの4置換体のNMRスペクトルは以下の特性吸収を示した(図2)。
1H-NMR(500MHz、DMSO-d6):0.85ppm(t、12H)、1.30ppm(m、8H)、1.47ppm(m、8H)、1.54ppm(s、6H)、3.38(t、8H)、4.42(s、8H)、6.99(s、4H)、8.19(s、2H)。
200mL四口フラスコにTM-BIP-A(4.00g、0.011mol、本州化学工業(株)製、式(4-24))、触媒用イオン交換樹脂として洗浄済みの15JWET(16.00g、商品名Amberlist、ダウ・ケミカル社製)を加え、1-プロパノール(80.00g、関東化学(株)製)を仕込み撹拌し、リフラックス温度で重合を開始した。4時間後30℃まで放冷後、15JWETをろ過し30℃減圧下で2時間濃縮、乾燥させ、目的とする材料(式(3-16)に相当する化合物を中心に式(3-13)、式(3-14)、式(3-15)で示される化合物が混合されていた。以下TPOM-BIP-Aと略す)5.0gを得た。
1H-NMRにより構造解析を行い、目的の化合物が得られていることを確認した。また、HPLCによりTPOM-BIP―Aの4置換体の存在比率が、TPOM-BIP―A全体中に94モル%であることを確認した。
TPOM-BIP―Aの4置換体のNMRスペクトルは以下の特性吸収を示した(図3)。
1H-NMR(500MHz、DMSO-d6):0.84ppm(t、12H)、1.49ppm(m、8H)、1.55ppm(s、6H)、3.34(t、8H)、4.43(s、8H)、7.00(s、4H)、8.19(s、2H)。
200mL四口フラスコにTM-BIP-A(4.00g、0.011mol、本州化学工業(株)製、式(4-24))、触媒用イオン交換樹脂として洗浄済みの15JWET(16.00g、商品名Amberlist、ダウ・ケミカル社製)を加え、エタノール(80.00g、関東化学(株)製)を仕込み撹拌し、リフラックス温度で重合を開始した。19.5時間後30℃まで放冷後、15JWETをろ過し30℃減圧下で2時間濃縮、乾燥させ、目的とする材料(式(3-20)に相当する化合物を中心に式(3-17)、式(3-18)、式(3-19)で示される化合物が混合されていた。以下TEOM-BIP-Aと略す)4.2gを得た。
1H-NMRにより構造解析を行い、目的の化合物が得られていることを確認した。また、HPLCによりTEOM-BIP-Aの4置換体の存在比率が、TEOM-BIP-A全体中に95モル%であることを確認した。
TEOM-BIP-Aの4置換体のNMRスペクトルは以下の特性吸収を示した(図4)。
1H-NMR(500MHz、DMSO-d6):1.10ppm(t、12H)、1.55ppm(s、6H)、3.44(q、8H)、4.42(s、8H)、6.99(s、4H)、8.22(s、2H)。
200mL四口フラスコにTM-BIP-A(4.00g、0.011mol、本州化学工業(株)製、式(4-24))、触媒用イオン交換樹脂として洗浄済みの15JWET(16.00g、商品名Amberlist、ダウ・ケミカル社製)を加え、2-メチル-1-プロパノール(80.00g、関東化学(株)製)を仕込み撹拌し、100℃で重合を開始した。4時間後30℃まで放冷後、15JWETをろ過し30℃減圧下で2時間濃縮、乾燥させ、目的とする材料(式(3-24)に相当する化合物を中心に式(3-21)、式(3-22)、式(3-23)で示される化合物が混合されていた。以下TIBOM-BIP-Aと略す)5.8gを得た。
1H-NMRにより構造解析を行い、目的の化合物が得られていることを確認した。また、HPLCによりTIBOM-BIP―Aの4置換体の存在比率が、TIBOM-BIP―A全体中に95モル%であることを確認した。
TIBOM-BIP―Aの4置換体のNMRスペクトルは以下の特性吸収を示した(図5)。
1H-NMR(500MHz、DMSO-d6):0.83ppm(d、24H)、1.55ppm(s、6H)、1.77(m、4H)、3.15(t、8H)、4.44(s、8H)、7.01(s、4H)、8.16(s、2H)。
200mL四口フラスコにTM-BIP-A(4.00g、0.011mol、本州化学工業(株)製、式(4-24))、触媒用イオン交換樹脂として洗浄済みの15JWET(16.00g、商品名Amberlist、ダウ・ケミカル社製)を加え、2-メトキシエタノール(80.00g、関東化学(株)製)を仕込み撹拌し、100℃で重合を開始した。1時間後30℃まで放冷後、15JWETをろ過し30℃減圧下で2時間濃縮、乾燥させ、目的とする材料(式(3-28)に相当する化合物を中心に式(3-25)、式(3-26)、式(3-27)で示される化合物が混合されていた。以下EGME-BIP-Aと略す)5.3gを得た。
1H-NMRにより構造解析を行い、目的の化合物が得られていることを確認した。また、HPLCによりEGME-BIP―Aの4置換体の存在比率が、EGME-BIP―A全体中に94モル%であることを確認した。
EGME-BIP―Aの4置換体のNMRスペクトルは以下の特性吸収を示した(図6)。
1H-NMR(500MHz、DMSO-d6):1.55ppm(s、6H)、3.23ppm(s、12H)、3.44ppm(m、8H)、3.53ppm(m、8H)、4.46(s、8H)、7.01(s、4H)、8.20(s、2H)。
200mL四口フラスコにTM-BIP-A(4.00g、0.011mol、本州化学工業(株)製、式(4-24))、触媒用イオン交換樹脂として洗浄済みの15JWET(16.00g、商品名Amberlist、ダウ・ケミカル社製)を加え、2-エトキシエタノール(80.00g、関東化学(株)製)を仕込み撹拌し、100℃で重合を開始した。1時間後30℃まで放冷後、15JWETをろ過し30℃減圧下で2時間濃縮、乾燥させ、目的とする材料(式(3-32)に相当する化合物を中心に式(3-29)、式(3-30)、式(3-31)で示される化合物が混合されていた。以下EGEE-BIP-Aと略す)3.0gを得た。
1H-NMRにより構造解析を行い、目的の化合物が得られていることを確認した。また、HPLCによりEGEE-BIP-Aの4置換体の存在比率が、EGEE-BIP-A全体中に92モル%であることを確認した。
EGEE-BIP-Aの4置換体のNMRスペクトルは以下の特性吸収を示した(図7)。
1H-NMR(500MHz、DMSO-d6):1.09ppm(t、12H)、1.55ppm(s、6H)、3.42ppm(m、8H)、3.5ppm(m、16H)、4.46(s、8H)、7.01(s、4H)、8.17(s、2H)。
200mL四口フラスコにTM-BIP-A(4.00g、0.011mol、本州化学工業(株)製、式(4-24))、触媒用イオン交換樹脂として洗浄済みの15JWET(16.00g、商品名Amberlist、ダウ・ケミカル社製)を加え、PGME(80.00g、関東化学(株)製)を仕込み撹拌し、100℃で重合を開始した。1時間後30℃まで放冷後、15JWETをろ過し30℃減圧下で2時間濃縮、乾燥させ、目的とする材料(式(3-36)に相当する化合物を中心に式(3-33)、式(3-34)、式(3-35)で示される化合物が混合されていた。以下PGME-BIP-Aと略す)3.0gを得た。
1H-NMRにより構造解析を行い、目的の化合物が得られていることを確認した。また、HPLCによりPGME-BIP-Aの4置換体の存在比率が、PGME-BIP-A全体中に74モル%であることを確認した。
PGME-BIP-Aの4置換体のNMRスペクトルは以下の特性吸収を示した(図8)。
1H-NMR(500MHz、DMSO-d6):1.06ppm(d、12H)、1.55ppm(s、6H)、3.25ppm(s、12H)、3.30ppm(m、8H)、3.63ppm(m、4H)、4.51(q、8H)、7.02(s、4H)、8.07(s、2H)。
200mL四口フラスコにTM-BIP-A(4.00g、0.011mol、本州化学工業(株)製、式(4-24))、触媒用イオン交換樹脂として洗浄済みの15JWET(8.00g、商品名Amberlist、ダウ・ケミカル社製)を加え、エチレングリコールイソプロピルエーテル(80.00g、関東化学(株)製)を仕込み撹拌し、40℃で重合を開始した。22時間後70℃まで昇温して12時間反応させて、放冷後、15JWETをろ過し30℃減圧下で2時間濃縮、乾燥させ、目的とする材料(式(3-40)に相当する化合物を中心に式(3-37)、式(3-38)、式(3-39)で示される化合物が混合されていた。以下EGIPE-BIP-Aと略す)3.0gを得た。
1H-NMRにより構造解析を行い、目的の化合物が得られていることを確認した。また、HPLCによりEGIPE-BIP-Aの4置換体の存在比率が、EGIPE-BIP-A全体中に84モル%であることを確認した。
EGIPE-BIP-Aの4置換体のNMRスペクトルは以下の特性吸収を示した(図9)。
1H-NMR(500MHz、DMSO-d6):1.07ppm(t、24H)、1.55ppm(s、6H)、3.45-3.57ppm(m、20H)、4.47(s、8H)、7.00(s、4H)、8.14(s、2H)。
100mL四口フラスコにN-フェニル-1-ナフチルアミン(10.00g、0.046mol、東京化成工業(株)製)、1-ナフトアルデヒド(7.12g、0.046mol、東京化成工業(株)製)、パラトルエンスルホン酸一水和物(0.908g、0.0046mol、関東化学(株)製)を加え、1,4-ジオキサン(21.03g、関東化学(株)製)を仕込み撹拌し、110℃まで昇温し溶解させ重合を開始した。12時間後室温まで放冷後、メタノール(400g、関東化学(株)製)へ再沈殿させた。得られた沈殿物をろ過し、減圧乾燥機で50℃、10時間さらに120℃、24時間乾燥し、目的とするポリマー(式(5-1)に相当)、以下pNPNA-NAと略す)11.6gを得た。pNPNA-NAのGPCによるポリスチレン換算で測定される重量平均分子量Mwは1400、多分散度Mw/Mnは1.62であった。
合成例12で得たpNPNA-NA樹脂0.51gに、架橋剤として合成例1のTMOM-BP-PGMEを0.10g、触媒にpPTS(ピリジニウムパラトルエンスルホネート)0.02g、界面活性剤としてメガファックR-30N(大日本インキ化学(株)製、商品名)0.001gを混合し、7.16gのPGMEA(プロピレングリコールモノメチルエーテルアセテート)、1.52gのPGME及び2.39gのシクロヘキサノンに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例12で得たpNPNA-NA樹脂0.51gに、架橋剤として合成例2のTMOM-BP-PGME2を0.10g、触媒にpPTS0.02g、界面活性剤としてメガファックR-30N(大日本インキ化学(株)製、商品名)0.001gを混合し、7.16gのPGMEA(プロピレングリコールモノメチルエーテルアセテート)、1.52gのPGME及び2.39gのシクロヘキサノンに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例12で得たpNPNA-NA樹脂0.51gに、架橋剤として合成例3のTBOM-BP-BUを0.10g、触媒にpPTS0.02g、界面活性剤としてメガファックR-30N(大日本インキ化学(株)製、商品名)0.001gを混合し、7.16gのPGMEA(プロピレングリコールモノメチルエーテルアセテート)、1.52gのPGME及び2.39gのシクロヘキサノンに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例12で得たpNPNA-NA樹脂0.51gに、架橋剤として合成例4のTBOM-BIP―Aを0.10g、触媒にpPTS0.02g、界面活性剤としてメガファックR-30N(大日本インキ化学(株)製、商品名)0.001gを混合し、7.16gのPGMEA(プロピレングリコールモノメチルエーテルアセテート)、1.52gのPGME及び2.39gのシクロヘキサノンに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例12で得たpNPNA-NA樹脂0.51gに、架橋剤として合成例5のTPOM-BIP―Aを0.10g、触媒にpPTS0.02g、界面活性剤としてメガファックR-30N(大日本インキ化学(株)製、商品名)0.001gを混合し、7.16gのPGMEA(プロピレングリコールモノメチルエーテルアセテート)、1.52gのPGME及び2.39gのシクロヘキサノンに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例12で得たpNPNA-NA樹脂0.51gに、架橋剤として合成例6のTEOM-BIP-Aを0.10g、触媒にpPTS0.02g、界面活性剤としてメガファックR-30N(大日本インキ化学(株)製、商品名)0.001gを混合し、7.16gのPGMEA(プロピレングリコールモノメチルエーテルアセテート)、1.52gのPGME及び2.39gのシクロヘキサノンに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例12で得たpNPNA-NA樹脂0.51gに、架橋剤として合成例7のTIBOM-BIP―Aを0.10g、触媒にpPTS0.02g、界面活性剤としてメガファックR-30N(大日本インキ化学(株)製、商品名)0.001gを混合し、7.16gのPGMEA(プロピレングリコールモノメチルエーテルアセテート)、1.52gのPGME及び2.39gのシクロヘキサノンに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例12で得たpNPNA-NA樹脂0.51gに、架橋剤として合成例8のEGME-BIP―Aを0.10g、触媒にpPTS0.02g、界面活性剤としてメガファックR-30N(大日本インキ化学(株)製、商品名)0.001gを混合し、7.16gのPGMEA(プロピレングリコールモノメチルエーテルアセテート)、1.52gのPGME及び2.39gのシクロヘキサノンに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例12で得たpNPNA-NA樹脂0.51gに、架橋剤として合成例9のEGEE-BIP-Aを0.10g、触媒にpPTS0.02g、界面活性剤としてメガファックR-30N(大日本インキ化学(株)製、商品名)0.001gを混合し、7.16gのPGMEA(プロピレングリコールモノメチルエーテルアセテート)、1.52gのPGME及び2.39gのシクロヘキサノンに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例12で得たpNPNA-NA樹脂0.51gに、架橋剤として合成例10のPGME-BIP-Aを0.10g、触媒にpPTS0.02g、界面活性剤としてメガファックR-30N(大日本インキ化学(株)製、商品名)0.001gを混合し、7.16gのPGMEA(プロピレングリコールモノメチルエーテルアセテート)、1.52gのPGME及び2.39gのシクロヘキサノンに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例12で得たpNPNA-NA樹脂0.51gに、架橋剤として合成例11のEGIPE-BIP-Aを0.10g、触媒にpPTS0.02g、界面活性剤としてメガファックR-30N(大日本インキ化学(株)製、商品名)0.001gを混合し、7.16gのPGMEA(プロピレングリコールモノメチルエーテルアセテート)、1.52gのPGME及び2.39gのシクロヘキサノンに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例12で得たpNPNA-NA樹脂0.51gに、架橋剤としてTMOM-BP(本州化学工業(株)製、式(4-23))を0.10g、触媒にpPTS0.02g、界面活性剤としてメガファックR-30N(大日本インキ化学(株)製、商品名)0.001gを混合し、7.16gのPGMEA(プロピレングリコールモノメチルエーテルアセテート)、1.52gのPGME及び2.39gのシクロヘキサノンに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例12で得たpNPNA-NA樹脂0.51gに、架橋剤としてTM-BIP-A(本州化学工業(株)製、式(4-24))を0.10g、触媒にpPTS0.02g、界面活性剤としてメガファックR-30N(大日本インキ化学(株)製、商品名)0.001gを混合し、PGMEA(プロピレングリコールモノメチルエーテルアセテート)7.16g、PGME1.52g及びシクロヘキサノン2.39gに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例12で得たpNPNA-NA樹脂0.51gに、架橋剤としてテトラメトキシメチルグリコリールウリルを0.10g、触媒に0.02gのpPTS、界面活性剤としてメガファックR-30N(大日本インキ化学(株)製、商品名)0.001gを混合し、7.16gのPGMEA(プロピレングリコールモノメチルエーテルアセテート)、1.52gのPGME及び2.39gのシクロヘキサノンに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
合成例12で得たpNPNA-NA樹脂0.51gに、架橋剤としてテトラブトキシメチルグリコリールウリルを0.10g、触媒に0.02gのpPTS、界面活性剤としてメガファックR-30N(大日本インキ化学(株)製、商品名)0.001gを混合し、7.16gのPGMEA(プロピレングリコールモノメチルエーテルアセテート)、1.52gのPGME及び2.39gのシクロヘキサノンに溶解させ溶液とした。その後、孔径0.10μmのポリエチレン製ミクロフィルターを用いて濾過し、更に、孔径0.05μmのポリエチレン製ミクロフィルターを用いて濾過して、多層膜によるリソグラフィープロセスに用いるレジスト下層膜形成組成物の溶液を調製した。
昇華物量の測定は国際公開第2007/111147号パンフレットに記載されている昇華物量測定装置を用いて実施した。まず、直径4インチのシリコンウェハー基板に、実施例1乃至実施例11、比較例1乃至比較例4で調製したレジスト下層膜形成組成物をスピンコーターにて、膜厚100nmとなるように塗布した。レジスト下層膜が塗布されたウェハーをホットプレートが一体化した前記昇華物量測定装置にセットし、120秒間ベークし、昇華物をQCM(Quartz Crystal Microbalance)センサー、すなわち電極が形成された水晶振動子に捕集した。QCMセンサーは、水晶振動子の表面(電極)に昇華物が付着するとその質量に応じて水晶振動子の周波数が変化する(下がる)性質を利用して、微量の質量変化を測定することができる。
得られた周波数変化を、測定に使用した水晶振動子の固有値からグラムに換算し、レジスト下層膜が塗布されたウェハー1枚の昇華物量と時間経過との関係を明らかにした。尚、最初の60秒間は装置安定化のために放置した(ウェハーをセットしていない)時間帯であり、ウェハーをホットプレートに載せた60秒の時点から180秒の時点までの測定値がウェハーの昇華物量に関する測定値である。当該装置から定量したレジスト下層膜の昇華物量を昇華物量比として表1に示す。尚、昇華物量は2000ngを上限として、それ以下であれば良好であるとし、それ以上であれば不良であると定義した。2000ng以下のものを○、以上のものを×で表す。
実施例1~11及び比較例1~4で調製したレジスト下層膜形成組成物の溶液を、それぞれスピンコーターを用いてシリコンウェハー上に塗布した。ホットプレート上で400℃2分間焼成し、レジスト下層膜(膜厚0.25μm)を形成した。このレジスト下層膜をレジストに使用する溶剤、例えば乳酸エチル、ならびにプロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、シクロヘキサノンに浸漬し、その溶剤に不溶であることを確認した。
上記で得られたレジスト下層膜形成組成物が、ホール内を良好に埋め込み出来るかについて評価を行った。スピンコーターにより、ホール(ホール直径:0.120nm、ピッチ:ホール直径/ホール間スペースの比=1/0.8、ホールの深さ:400nm)が形成されたテトラエチルオルソシリケート(TEOS)基板上にレジスト下層膜形成物を塗布した。その後、ホットプレート上で240℃1分間加熱し、レジスト下層膜(リソグラフィー用ギャップフィル材の用途とする場合)を膜厚約120nmで形成した。走査型電子顕微鏡(SEM)を用いて、実施例1~11、及び比較例1~4で得たレジスト下層膜形成物を塗布したホールを有するTEOS基板の断面形状を観察することにより、埋め込み性を評価した。レジスト下層膜がホール内に隙間無く形成されている場合を埋め込み性が良好(「○」)とみなし、ホールに埋め込まれていない又はホール中に穴や隙間が存在している場合には不良(「×」)とした。
Claims (16)
- 樹脂、及び下記式(1)又は式(2):
(式中、Q1は単結合又はm1価の有機基を示し、R1及びR4はそれぞれ炭素原子数2乃至10のアルキル基、又は炭素原子数1乃至10のアルコキシ基を有する炭素原子数2乃至10のアルキル基を示し、R2及びR5はそれぞれ水素原子又はメチル基を示し、R3及びR6はそれぞれ炭素原子数1乃至10のアルキル基、又は炭素原子数6乃至40のアリール基を示す。
n1は1≦n1≦3の整数、n2は2≦n2≦5の整数、n3は0≦n3≦3の整数、n4は0≦n4≦3の整数、3≦(n1+n2+n3+n4)≦6の整数を示す。
n5は1≦n5≦3の整数、n6は1≦n6≦4の整数、n7は0≦n7≦3の整数、n8は0≦n8≦3の整数、2≦(n5+n6+n7+n8)≦5の整数を示す。m1は2乃至10の整数を示す。)で示される架橋性化合物を含むレジスト下層膜形成組成物。 - Q1が単結合、又は炭素原子数1乃至10の鎖状炭化水素基、炭素原子数6乃至40の芳香族基、若しくはそれらの組み合わせから選ばれるm1価の有機基である請求項1に記載のレジスト下層膜形成組成物。
- 上記式(1)又は式(2)で示される架橋性化合物が、下記式(3)又は式(4)で示される化合物と、ヒドロキシル基含有エーテル化合物又は炭素原子数2乃至10のアルコールとの反応によって得られるものである請求項1又は請求項2に記載のレジスト下層膜形成組成物。
(式中、Q2は単結合又はm2価の有機基を示す。R8、R9、R11及びR12はそれぞれ水素原子又はメチル基を示し、R7及びR10はそれぞれ炭素原子数1乃至10のアルキル基、又は炭素原子数6乃至40のアリール基を示す。
n9は1≦n9≦3の整数、n10は2≦n10≦5の整数、n11は0≦n11≦3の整数、n12は0≦n12≦3の整数、3≦(n9+n10+n11+n12)≦6の整数を示す。
n13は1≦n13≦3の整数、n14は1≦n14≦4の整数、n15は0≦n15≦3の整数、n16は0≦n16≦3の整数、2≦(n13+n14+n15+n16)≦5の整数を示す。m2は2乃至10の整数を示す。) - 下記式(3)又は式(4)で示される化合物と、ヒドロキシル基含有エーテル化合物又は炭素原子数2乃至10のアルコールとの反応が酸触媒の存在下で行われる請求項3に記載のレジスト下層膜形成組成物。
- 酸触媒が触媒用イオン交換樹脂である請求項4に記載のレジスト下層膜形成組成物。
- ヒドロキシル基含有エーテル化合物がプロピレングリコールモノメチルエーテル又はプロピレングリコールモノエチルエーテルである請求項3乃至請求項5のいずれか1項に記載のレジスト下層膜形成組成物。
- 炭素原子数2乃至10のアルコールが、エタノール、1-プロパノール、2-メチル-1-プロパノール、ブタノール、2-メトキシエタノール又は2-エトキシエタノールである請求項3乃至請求項5のいずれか1項に記載のレジスト下層膜形成組成物。
- 樹脂がノボラック樹脂である請求項1乃至請求項7のいずれか1項に記載のレジスト下層膜形成組成物。
- 更に架橋剤を含む請求項1乃至請求項8のいずれか1項に記載のレジスト下層膜形成組成物。
- 更に酸及び/又は酸発生剤を含む請求項1乃至請求項9のいずれか1項に記載のレジスト下層膜形成組成物。
- 請求項1乃至請求項10のいずれか1項に記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成することによって得られるレジスト下層膜。
- 請求項1乃至請求項10のいずれか1項に記載のレジスト下層膜形成組成物を半導体基板上に塗布し焼成してレジスト下層膜を形成する工程を含む半導体の製造に用いるレジストパターンの形成方法。
- 半導体基板上に請求項1乃至請求項10のいずれか1項に記載のレジスト下層膜形成組成物によりレジスト下層膜を形成する工程、その上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、形成されたレジストパターンにより該レジスト下層膜をエッチングする工程、及びパターン化されたレジスト下層膜により半導体基板を加工する工程を含む半導体装置の製造方法。
- 半導体基板上に請求項1乃至請求項10のいずれか1項に記載のレジスト下層膜形成組成物によりレジスト下層膜を形成する工程、その上にハードマスクを形成する工程、更にその上にレジスト膜を形成する工程、光又は電子線の照射と現像によりレジストパターンを形成する工程、形成されたレジストパターンによりハードマスクをエッチングする工程、パターン化されたハードマスクにより該レジスト下層膜をエッチングする工程、及びパターン化されたレジスト下層膜により半導体基板を加工する工程を含む半導体装置の製造方法。
- ハードマスクが無機物の塗布又は無機物の蒸着により形成されたものである請求項14に記載の製造方法。
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201910993087.XA CN110698331B (zh) | 2013-06-26 | 2014-06-24 | 包含被置换的交联性化合物的抗蚀剂下层膜形成用组合物 |
KR1020157035256A KR102276783B1 (ko) | 2013-06-26 | 2014-06-24 | 치환된 가교성 화합물을 포함하는 레지스트 하층막 형성 조성물 |
US14/900,384 US10809619B2 (en) | 2013-06-26 | 2014-06-24 | Resist underlayer film-forming composition containing substituted crosslinkable compound |
JP2015524057A JP6478051B2 (ja) | 2013-06-26 | 2014-06-24 | 置換された架橋性化合物を含むレジスト下層膜形成組成物 |
CN201480035763.8A CN105324720B (zh) | 2013-06-26 | 2014-06-24 | 包含被置换的交联性化合物的抗蚀剂下层膜形成用组合物 |
US16/986,921 US20200379352A1 (en) | 2013-06-26 | 2020-08-06 | Resist underlayer film-forming composition containing substituted crosslinkable compound |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013-134277 | 2013-06-26 | ||
JP2013134277 | 2013-06-26 | ||
JP2013-151934 | 2013-07-22 | ||
JP2013151934 | 2013-07-22 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US14/900,384 A-371-Of-International US10809619B2 (en) | 2013-06-26 | 2014-06-24 | Resist underlayer film-forming composition containing substituted crosslinkable compound |
US16/986,921 Division US20200379352A1 (en) | 2013-06-26 | 2020-08-06 | Resist underlayer film-forming composition containing substituted crosslinkable compound |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2014208542A1 true WO2014208542A1 (ja) | 2014-12-31 |
Family
ID=52141875
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2014/066680 WO2014208542A1 (ja) | 2013-06-26 | 2014-06-24 | 置換された架橋性化合物を含むレジスト下層膜形成組成物 |
Country Status (6)
Country | Link |
---|---|
US (2) | US10809619B2 (ja) |
JP (2) | JP6478051B2 (ja) |
KR (1) | KR102276783B1 (ja) |
CN (2) | CN110698331B (ja) |
TW (1) | TWI626263B (ja) |
WO (1) | WO2014208542A1 (ja) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016138945A (ja) * | 2015-01-26 | 2016-08-04 | Jsr株式会社 | 多層レジストプロセス用レジスト下層膜形成組成物及びレジスト下層膜の形成方法 |
WO2017002653A1 (ja) * | 2015-07-02 | 2017-01-05 | 日産化学工業株式会社 | 長鎖アルキル基を有するエポキシ付加体を含むレジスト下層膜形成組成物 |
KR20180070561A (ko) | 2015-10-19 | 2018-06-26 | 닛산 가가쿠 고교 가부시키 가이샤 | 장쇄 알킬기함유 노볼락을 포함하는 레지스트 하층막 형성 조성물 |
WO2019013293A1 (ja) * | 2017-07-14 | 2019-01-17 | 日産化学株式会社 | レジスト下層膜形成組成物、レジスト下層膜、レジストパターンの形成方法及び半導体装置の製造方法 |
KR20190046807A (ko) | 2016-09-01 | 2019-05-07 | 닛산 가가쿠 가부시키가이샤 | 트리아릴디아민함유 노볼락 수지를 포함하는 레지스트 하층막 형성 조성물 |
WO2019172156A1 (ja) * | 2018-03-07 | 2019-09-12 | 富士フイルム株式会社 | インプリント用下層膜形成組成物、インプリント用硬化性組成物、キット |
TWI693476B (zh) * | 2015-01-27 | 2020-05-11 | 日商富士軟片股份有限公司 | 組成物、膜、空白遮罩、抗蝕劑圖案形成方法以及電子元件的製造方法 |
TWI703407B (zh) * | 2015-08-31 | 2020-09-01 | 日商三菱瓦斯化學股份有限公司 | 微影用下層膜形成材料、微影用下層膜形成用組成物、微影用下層膜及其製造方法、以及阻劑圖型形成方法 |
KR20200123117A (ko) | 2018-02-20 | 2020-10-28 | 닛산 가가쿠 가부시키가이샤 | 방향족 비닐 화합물이 부가된 트리아릴디아민함유노볼락 수지를 포함하는 레지스트 하층막 형성 조성물 |
WO2021125036A1 (ja) * | 2019-12-18 | 2021-06-24 | 日産化学株式会社 | ナノインプリント用レジスト下層膜形成組成物 |
WO2022050405A1 (ja) | 2020-09-07 | 2022-03-10 | 日産化学株式会社 | ウェハー処理方法 |
KR20240074784A (ko) | 2021-10-11 | 2024-05-28 | 닛산 가가쿠 가부시키가이샤 | 레지스트 하층막 형성 조성물 |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106133607B (zh) * | 2014-03-31 | 2020-01-03 | 日产化学工业株式会社 | 含有芳香族乙烯基化合物加成的酚醛清漆树脂的抗蚀剂下层膜形成用组合物 |
CN108713164B (zh) * | 2016-03-09 | 2022-03-18 | 日产化学工业株式会社 | 抗蚀剂下层膜形成用组合物及使用了该组合物的抗蚀剂图案的形成方法 |
JP6997416B2 (ja) * | 2016-03-10 | 2022-01-17 | 日産化学株式会社 | 炭素原子間の不飽和結合による光架橋基を有する化合物を含む段差基板被覆組成物 |
KR102452808B1 (ko) * | 2016-06-16 | 2022-10-07 | 동우 화인켐 주식회사 | 하드마스크용 조성물 |
CN106800629B (zh) * | 2017-01-12 | 2018-10-23 | 台州学院 | 一种富羟基的多孔芘基有机骨架材料及其制备方法 |
CN112513737A (zh) * | 2018-07-31 | 2021-03-16 | 三菱瓦斯化学株式会社 | 下层膜形成组合物 |
CN115947648A (zh) * | 2022-12-28 | 2023-04-11 | 北京彤程创展科技有限公司 | 一种交联剂及其制备方法、光刻胶 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010147155A1 (ja) * | 2009-06-19 | 2010-12-23 | 日産化学工業株式会社 | カルバゾールノボラック樹脂 |
WO2011040340A1 (ja) * | 2009-09-29 | 2011-04-07 | Jsr株式会社 | パターン形成方法及びレジスト下層膜形成用組成物 |
JP2011520148A (ja) * | 2008-05-06 | 2011-07-14 | エイゼット・エレクトロニック・マテリアルズ・ユーエスエイ・コーポレイション | 反射防止コーティング組成物 |
JP2012515369A (ja) * | 2009-01-16 | 2012-07-05 | フジフィルム・エレクトロニック・マテリアルズ・ユーエスエイ・インコーポレイテッド | 半導体基板コーティングのための非ポリマーバインダー |
Family Cites Families (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3035091A (en) * | 1959-12-07 | 1962-05-15 | Monsanto Chemicals | Carboxylated bisphenol compounds |
US4314925A (en) * | 1979-10-02 | 1982-02-09 | The Dow Chemical Company | Curable compositions |
US6132935A (en) * | 1995-12-19 | 2000-10-17 | Fuji Photo Film Co., Ltd. | Negative-working image recording material |
JP3798504B2 (ja) * | 1997-04-21 | 2006-07-19 | 富士写真フイルム株式会社 | ネガ型画像記録材料 |
JP3810538B2 (ja) * | 1997-11-28 | 2006-08-16 | 富士写真フイルム株式会社 | ポジ型画像形成材料 |
JP3929653B2 (ja) * | 1999-08-11 | 2007-06-13 | 富士フイルム株式会社 | ネガ型レジスト組成物 |
JP3790960B2 (ja) * | 2001-10-19 | 2006-06-28 | 富士写真フイルム株式会社 | ネガ型レジスト組成物 |
JP2003270779A (ja) * | 2002-01-11 | 2003-09-25 | Fuji Photo Film Co Ltd | ネガ型レジスト組成物 |
JP4612672B2 (ja) | 2004-03-12 | 2011-01-12 | フジフィルム・エレクトロニック・マテリアルズ・ユーエスエイ・インコーポレイテッド | リソグラフィ用途のための熱硬化性アンダーコート |
JP5211438B2 (ja) * | 2005-06-09 | 2013-06-12 | 東レ株式会社 | 樹脂組成物およびそれを用いた表示装置 |
JP2008143302A (ja) | 2006-12-08 | 2008-06-26 | Mazda Motor Corp | 車両の車室内構造 |
KR101426980B1 (ko) | 2007-05-23 | 2014-08-06 | 제이에스알 가부시끼가이샤 | 레지스트 하층막 형성용 조성물 |
JP5115045B2 (ja) * | 2007-06-14 | 2013-01-09 | 東レ株式会社 | ポリイミドワニス |
JP5141882B2 (ja) | 2008-01-24 | 2013-02-13 | 日産化学工業株式会社 | バリア性を示すレジスト下層膜の形成用組成物及びレジスト下層膜のバリア性評価方法 |
JP5206214B2 (ja) * | 2008-08-11 | 2013-06-12 | 東レ株式会社 | ポジ型感光性樹脂組成物 |
JP5779835B2 (ja) * | 2008-09-30 | 2015-09-16 | 大日本印刷株式会社 | 架橋剤、ネガ型レジスト組成物、並びに、当該レジスト組成物を用いたパターン形成方法及び電子部品 |
KR101596985B1 (ko) * | 2009-01-29 | 2016-02-23 | 도레이 카부시키가이샤 | 수지 조성물 및 이것을 이용한 표시 장치 |
JP5382321B2 (ja) | 2009-03-31 | 2014-01-08 | 日産化学工業株式会社 | レジスト下層膜形成組成物及びそれを用いたレジストパターンの形成方法 |
KR101764259B1 (ko) * | 2009-06-02 | 2017-08-03 | 닛산 가가쿠 고교 가부시키 가이샤 | 설파이드 결합을 갖는 실리콘 함유 레지스트 하층막 형성 조성물 |
JP5582316B2 (ja) * | 2009-08-10 | 2014-09-03 | 日産化学工業株式会社 | ポリマー型の光酸発生剤を含有するレジスト下層膜形成組成物及びそれを用いたレジストパターンの形成方法 |
KR101749601B1 (ko) * | 2009-09-16 | 2017-06-21 | 닛산 가가쿠 고교 가부시키 가이샤 | 설폰아미드기를 가지는 실리콘 함유 레지스트 하층막 형성 조성물 |
JP5485188B2 (ja) * | 2011-01-14 | 2014-05-07 | 信越化学工業株式会社 | レジスト下層膜材料及びこれを用いたパターン形成方法 |
WO2014126626A1 (en) * | 2013-02-15 | 2014-08-21 | Empire Technology Development Llc | Phenolic epoxy compounds |
-
2014
- 2014-06-24 KR KR1020157035256A patent/KR102276783B1/ko active IP Right Grant
- 2014-06-24 US US14/900,384 patent/US10809619B2/en active Active
- 2014-06-24 CN CN201910993087.XA patent/CN110698331B/zh active Active
- 2014-06-24 CN CN201480035763.8A patent/CN105324720B/zh active Active
- 2014-06-24 WO PCT/JP2014/066680 patent/WO2014208542A1/ja active Application Filing
- 2014-06-24 JP JP2015524057A patent/JP6478051B2/ja active Active
- 2014-06-26 TW TW103122066A patent/TWI626263B/zh active
-
2018
- 2018-05-11 JP JP2018092295A patent/JP6593616B2/ja active Active
-
2020
- 2020-08-06 US US16/986,921 patent/US20200379352A1/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011520148A (ja) * | 2008-05-06 | 2011-07-14 | エイゼット・エレクトロニック・マテリアルズ・ユーエスエイ・コーポレイション | 反射防止コーティング組成物 |
JP2012515369A (ja) * | 2009-01-16 | 2012-07-05 | フジフィルム・エレクトロニック・マテリアルズ・ユーエスエイ・インコーポレイテッド | 半導体基板コーティングのための非ポリマーバインダー |
WO2010147155A1 (ja) * | 2009-06-19 | 2010-12-23 | 日産化学工業株式会社 | カルバゾールノボラック樹脂 |
WO2011040340A1 (ja) * | 2009-09-29 | 2011-04-07 | Jsr株式会社 | パターン形成方法及びレジスト下層膜形成用組成物 |
Cited By (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016138945A (ja) * | 2015-01-26 | 2016-08-04 | Jsr株式会社 | 多層レジストプロセス用レジスト下層膜形成組成物及びレジスト下層膜の形成方法 |
TWI693476B (zh) * | 2015-01-27 | 2020-05-11 | 日商富士軟片股份有限公司 | 組成物、膜、空白遮罩、抗蝕劑圖案形成方法以及電子元件的製造方法 |
WO2017002653A1 (ja) * | 2015-07-02 | 2017-01-05 | 日産化学工業株式会社 | 長鎖アルキル基を有するエポキシ付加体を含むレジスト下層膜形成組成物 |
KR20180025849A (ko) | 2015-07-02 | 2018-03-09 | 닛산 가가쿠 고교 가부시키 가이샤 | 장쇄알킬기를 갖는 에폭시부가체를 포함하는 레지스트 하층막 형성 조성물 |
JPWO2017002653A1 (ja) * | 2015-07-02 | 2018-04-19 | 日産化学工業株式会社 | 長鎖アルキル基を有するエポキシ付加体を含むレジスト下層膜形成組成物 |
TWI703407B (zh) * | 2015-08-31 | 2020-09-01 | 日商三菱瓦斯化學股份有限公司 | 微影用下層膜形成材料、微影用下層膜形成用組成物、微影用下層膜及其製造方法、以及阻劑圖型形成方法 |
JP2021157184A (ja) * | 2015-10-19 | 2021-10-07 | 日産化学株式会社 | 長鎖アルキル基含有ノボラックを含むレジスト下層膜形成組成物 |
KR20180070561A (ko) | 2015-10-19 | 2018-06-26 | 닛산 가가쿠 고교 가부시키 가이샤 | 장쇄 알킬기함유 노볼락을 포함하는 레지스트 하층막 형성 조성물 |
JP7208592B2 (ja) | 2015-10-19 | 2023-01-19 | 日産化学株式会社 | 長鎖アルキル基含有ノボラックを含むレジスト下層膜形成組成物 |
KR20190046807A (ko) | 2016-09-01 | 2019-05-07 | 닛산 가가쿠 가부시키가이샤 | 트리아릴디아민함유 노볼락 수지를 포함하는 레지스트 하층막 형성 조성물 |
US11300879B2 (en) | 2016-09-01 | 2022-04-12 | Nissan Chemical Corporation | Resist underlayer film forming composition containing triaryldiamine-containing novolac resin |
WO2019013293A1 (ja) * | 2017-07-14 | 2019-01-17 | 日産化学株式会社 | レジスト下層膜形成組成物、レジスト下層膜、レジストパターンの形成方法及び半導体装置の製造方法 |
US11169441B2 (en) | 2017-07-14 | 2021-11-09 | Nissan Chemical Corporation | Composition for forming resist underlayer film, resist underlayer film, method for forming resist pattern and method for producing semiconductor device |
JPWO2019013293A1 (ja) * | 2017-07-14 | 2020-05-07 | 日産化学株式会社 | レジスト下層膜形成組成物、レジスト下層膜、レジストパターンの形成方法及び半導体装置の製造方法 |
JP7368791B2 (ja) | 2017-07-14 | 2023-10-25 | 日産化学株式会社 | レジスト下層膜形成組成物、レジスト下層膜、レジストパターンの形成方法及び半導体装置の製造方法 |
KR20200123117A (ko) | 2018-02-20 | 2020-10-28 | 닛산 가가쿠 가부시키가이샤 | 방향족 비닐 화합물이 부가된 트리아릴디아민함유노볼락 수지를 포함하는 레지스트 하층막 형성 조성물 |
US12025916B2 (en) | 2018-02-20 | 2024-07-02 | Nissan Chemical Corporation | Resist underlayer film-forming composition that contains triaryldiamine-containing novolac resin to which aromatic vinyl compound is added |
JPWO2019172156A1 (ja) * | 2018-03-07 | 2021-03-04 | 富士フイルム株式会社 | インプリント用下層膜形成組成物、インプリント用硬化性組成物、キット |
JP7017623B2 (ja) | 2018-03-07 | 2022-02-08 | 富士フイルム株式会社 | インプリント用下層膜形成組成物、インプリント用硬化性組成物、キット |
WO2019172156A1 (ja) * | 2018-03-07 | 2019-09-12 | 富士フイルム株式会社 | インプリント用下層膜形成組成物、インプリント用硬化性組成物、キット |
WO2021125036A1 (ja) * | 2019-12-18 | 2021-06-24 | 日産化学株式会社 | ナノインプリント用レジスト下層膜形成組成物 |
WO2022050405A1 (ja) | 2020-09-07 | 2022-03-10 | 日産化学株式会社 | ウェハー処理方法 |
KR20240074784A (ko) | 2021-10-11 | 2024-05-28 | 닛산 가가쿠 가부시키가이샤 | 레지스트 하층막 형성 조성물 |
Also Published As
Publication number | Publication date |
---|---|
CN110698331B (zh) | 2022-07-19 |
US20200379352A1 (en) | 2020-12-03 |
KR102276783B1 (ko) | 2021-07-14 |
JP6593616B2 (ja) | 2019-10-23 |
US20160139509A1 (en) | 2016-05-19 |
TW201516081A (zh) | 2015-05-01 |
CN105324720B (zh) | 2020-01-03 |
US10809619B2 (en) | 2020-10-20 |
CN105324720A (zh) | 2016-02-10 |
TWI626263B (zh) | 2018-06-11 |
JPWO2014208542A1 (ja) | 2017-02-23 |
KR20160026875A (ko) | 2016-03-09 |
JP6478051B2 (ja) | 2019-03-06 |
JP2018154631A (ja) | 2018-10-04 |
CN110698331A (zh) | 2020-01-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6593616B2 (ja) | 置換された架橋性化合物を含むレジスト下層膜形成組成物 | |
US11720024B2 (en) | Resist underlayer film-forming composition containing indolocarbazole novolak resin | |
JP6974799B2 (ja) | 膜密度が向上したレジスト下層膜を形成するための組成物 | |
JP6124025B2 (ja) | 多核フェノール類を有するノボラック樹脂を含むレジスト下層膜形成組成物 | |
WO2013146670A1 (ja) | フェニルインドール含有ノボラック樹脂を含むレジスト下層膜形成組成物 | |
US11300879B2 (en) | Resist underlayer film forming composition containing triaryldiamine-containing novolac resin | |
JP7368791B2 (ja) | レジスト下層膜形成組成物、レジスト下層膜、レジストパターンの形成方法及び半導体装置の製造方法 | |
US12025916B2 (en) | Resist underlayer film-forming composition that contains triaryldiamine-containing novolac resin to which aromatic vinyl compound is added | |
WO2021200883A1 (ja) | 架橋剤の変性が抑制されたレジスト下層膜形成組成物 | |
US20230333474A1 (en) | Resist underlayer film-forming composition comprising fluoroalkyl group-containing organic acid or salt thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 201480035763.8 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 14818743 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2015524057 Country of ref document: JP Kind code of ref document: A |
|
ENP | Entry into the national phase |
Ref document number: 20157035256 Country of ref document: KR Kind code of ref document: A |
|
WWE | Wipo information: entry into national phase |
Ref document number: 14900384 Country of ref document: US |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 14818743 Country of ref document: EP Kind code of ref document: A1 |