JP2015131954A - 下層のための芳香族樹脂 - Google Patents
下層のための芳香族樹脂 Download PDFInfo
- Publication number
- JP2015131954A JP2015131954A JP2014251549A JP2014251549A JP2015131954A JP 2015131954 A JP2015131954 A JP 2015131954A JP 2014251549 A JP2014251549 A JP 2014251549A JP 2014251549 A JP2014251549 A JP 2014251549A JP 2015131954 A JP2015131954 A JP 2015131954A
- Authority
- JP
- Japan
- Prior art keywords
- aryl
- layer
- reaction product
- alkyl
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000003118 aryl group Chemical group 0.000 title claims description 176
- 229920005989 resin Polymers 0.000 title description 58
- 239000011347 resin Substances 0.000 title description 58
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 49
- 239000000178 monomer Substances 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 239000000758 substrate Substances 0.000 claims description 49
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 37
- 229920002120 photoresistant polymer Polymers 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 28
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 24
- 229910052710 silicon Inorganic materials 0.000 claims description 24
- 239000010703 silicon Substances 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 21
- 238000005530 etching Methods 0.000 claims description 18
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 239000004094 surface-active agent Substances 0.000 claims description 7
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 5
- 239000003431 cross linking reagent Substances 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
- 239000011707 mineral Chemical class 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 238000000059 patterning Methods 0.000 claims description 4
- 150000003460 sulfonic acids Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
- 239000004065 semiconductor Substances 0.000 abstract description 19
- 239000000463 material Substances 0.000 abstract description 18
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 230000003667 anti-reflective effect Effects 0.000 abstract description 4
- 239000002798 polar solvent Substances 0.000 abstract description 4
- 125000000962 organic group Chemical group 0.000 abstract 3
- 229920001577 copolymer Polymers 0.000 abstract 1
- 238000007334 copolymerization reaction Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 107
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
- -1 pyrenol compound Chemical class 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 235000012431 wafers Nutrition 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- BIJNHUAPTJVVNQ-UHFFFAOYSA-N 1-Hydroxypyrene Chemical class C1=C2C(O)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 BIJNHUAPTJVVNQ-UHFFFAOYSA-N 0.000 description 7
- 239000003377 acid catalyst Substances 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 238000001020 plasma etching Methods 0.000 description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 230000005855 radiation Effects 0.000 description 5
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 4
- 239000004971 Cross linker Substances 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229940116333 ethyl lactate Drugs 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 238000001459 lithography Methods 0.000 description 3
- 239000012454 non-polar solvent Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 210000002381 plasma Anatomy 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 description 2
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 2
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229940044654 phenolsulfonic acid Drugs 0.000 description 2
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000011342 resin composition Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- BZOVBIIWPDQIHF-UHFFFAOYSA-N 3-hydroxy-2-methylbenzenesulfonic acid Chemical compound CC1=C(O)C=CC=C1S(O)(=O)=O BZOVBIIWPDQIHF-UHFFFAOYSA-N 0.000 description 1
- 229940077398 4-methyl anisole Drugs 0.000 description 1
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- XGQJGMGAMHFMAO-UHFFFAOYSA-N COCN(C(C(N1COC)N2COC)N(COC)C2=O)C1=O Chemical compound COCN(C(C(N1COC)N2COC)N(COC)C2=O)C1=O XGQJGMGAMHFMAO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 229910000577 Silicon-germanium Inorganic materials 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- LEVVHYCKPQWKOP-UHFFFAOYSA-N [Si].[Ge] Chemical compound [Si].[Ge] LEVVHYCKPQWKOP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005042 acyloxymethyl group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000004849 alkoxymethyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000006117 anti-reflective coating Substances 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical class C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000007766 curtain coating Methods 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
- 238000011161 development Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000105 evaporative light scattering detection Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 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
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004377 microelectronic Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 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
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 239000010980 sapphire Substances 0.000 description 1
- 229910052594 sapphire Inorganic materials 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
- 238000007764 slot die coating Methods 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000010345 tape casting Methods 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- MAKDTFFYCIMFQP-UHFFFAOYSA-N titanium tungsten Chemical compound [Ti].[W] MAKDTFFYCIMFQP-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
-
- 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
-
- 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
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Abstract
Description
の1種以上の第1のモノマーと、式Ar−CHO(式中、Arは少なくとも2つの縮合芳香環を有するC10−C30芳香族部分であって、この芳香族部分は場合によっては、C1−C30アルキル、C2−C30アルケニル、C7−C30アラルキル、C6−C30アリール、置換C6−C30アリール、−OR3、−C1−C30アルキレン−OR3、および−C1−C30アルキリデン−OR3の1以上で置換されていてよく、R3はH、C1−C30アルキル、およびC6−C30アリールから選択される)の1種以上の第2のモノマーとを含む組み合わせ物から形成される反応生成物を提供する。
の1種以上の第1のモノマーと、式Ar−CHO(式中、Arは少なくとも2つの縮合芳香環を有するC10−C30芳香族部分であって、この芳香族部分は場合によっては、C1−C30アルキル、C2−C30アルケニル、C7−C30アラルキル、C6−C30アリール、置換C6−C30アリール、−OR3、−C1−C30アルキレン−OR3、および−C1−C30アルキリデン−OR3の1以上で置換されていてよく、R3はH、C1−C30アルキル、およびC6−C30アリールから選択される)の1種以上の第2のモノマーとを、酸の存在下で、および場合によっては溶媒中で、反応させることを含む上述の反応生成物を製造する方法も提供する。本発明は、上述の方法によって製造された反応生成物も提供する。
3つ口50mL丸底フラスコに機械式攪拌装置、サーモウェル(thermowell)および窒素入口を伴う凝縮器を取り付けた。このフラスコに、1−ピレノール(5.0g、0.0229モル)、2−ナフトアルデヒド(3.578g、0.0229モル)およびPGME(10mL)およびEtOH(7mL)を入れた。次いで、攪拌が開始され、この反応混合物は窒素下で60℃に加熱された。30分後に透明な溶液が得られ、そしてその時点で加熱が解除された。HCl(3.0mL、水中37%)がこの反応混合物に40℃で滴下添加された。この反応混合物は24時間還流され、濃厚で暗褐色の溶液を生じさせた。この反応混合物は室温まで冷却され、そして10mLのPGMEで希釈された。この混合物は、次いで、250mLのメタノールに添加され、薄灰色の沈殿物を生じさせた。沈殿した樹脂は濾過されて、60〜70℃で真空乾燥されて、4.3gの樹脂(試料1)を灰色粉体として得た。GPCによる分析:Mw=2321、多分散度(PDI)=1.24。
実施例1の手順が繰り返され、得られた樹脂(試料2)のGPCによる分析は以下の事項を提示した:Mw=2231、PDI=1.33。
3つ口50mL丸底フラスコに機械式攪拌装置、サーモウェルおよび窒素入口を伴う凝縮器を取り付けた。このフラスコに、1−ピレノール(4.0g、0.0183モル)、2−ナフトアルデヒド(2.8624g、0.0183モル)およびトルエン(24mL)を入れた。次いで、攪拌が開始され、この反応混合物は窒素下で60℃に加熱された。30分後に透明な溶液が得られ、そしてその時点で加熱が解除された。メタンスルホン酸(1.76g、0.0183モル)がこの反応混合物に40℃で滴下添加された。この反応混合物は100〜110℃に12時間にわたって加熱されて、濃厚な溶液を得た。この反応混合物は次いで室温まで冷却された。この混合物は250mLのメタノールに添加され、灰色の沈殿物を生じさせた。沈殿した樹脂は濾過されて、60〜70℃で真空乾燥されて、3.6gの樹脂(試料3)を灰色粉体として得た。GPCによる分析:Mw=2697、PDI=1.6。
表1に示される溶媒および酸が使用されたこと以外は、実施例1の手順が概して繰り返された。
2−ナフトアルデヒドが表2に列挙されるアルデヒドで置き換えられた以外は、実施例1の手順が繰り返される。
3つ口50mL丸底フラスコに機械式攪拌装置、サーモウェルおよび窒素入口を伴う凝縮器を取り付けた。このフラスコに、1−ピレノール(10.0g、0.0458モル)、2−ナフトアルデヒド(7.156g、0.0458モル)およびPGME(40mL)を入れた。次いで、攪拌が開始され、この反応混合物は窒素下で室温で攪拌された。30分後に透明な溶液が得られた。メタンスルホン酸(2.201g、0.0229モル)がこの反応混合物に添加された。この反応混合物は120℃で4時間にわたって加熱されて、濃厚な溶液を得た。この反応混合物は次いで室温まで冷却された。この混合物は400mLのメタノールおよび水(v/v=4:1)に添加され、灰色の沈殿物を生じさせた。沈殿した樹脂は濾過されて、60〜70℃で真空乾燥されて、11.3gの樹脂を灰色粉体(試料6)として得た。GPCによる分析:Mw=1229、PDI=1.2。
使用された1−ピレノール添加量と反応時間が表3に示されるものであった以外は、実施例6の手順が繰り返された。
3つ口50mL丸底フラスコに機械式攪拌装置、サーモウェルおよび窒素入口を伴う凝縮器を取り付けた。このフラスコに、1−ピレノール(5.0g、0.0229モル)、ベンズアルデヒド(2.431g、0.0229モル)、PGME(10mL)およびEtOH(7mL)を入れた。次いで、攪拌が開始され、この反応混合物は窒素下で60℃に加熱された。30分後に透明な溶液が得られ、その時点で加熱が解除された。HCl(3.0mL、水性37%)がこの反応混合物に40℃で滴下添加された。この反応混合物は24時間にわたって還流されて、濃厚な暗褐色溶液を得た。この反応混合物は室温まで冷却され、10mLのPGMEで希釈された。次いで、この混合物は500mLのメタノールに添加され、薄灰色の沈殿物を生じさせた。沈殿した樹脂は濾過されて、60〜70℃で真空乾燥されて、1.0gの樹脂(比較例1)を灰色粉体として得た。GPCによる分析:Mw=4526、PDI=1.88。
式(V)に示される繰り返し単位を有するポリマーの試料(比較例2)がGun Ei Chemicalから得られ、そしてそのまま使用された。この試料の分子量はMw=6066、およびMn=2362であった。
表5に列挙された芳香族樹脂反応生成物が個々にプロピレングリコールモノメチルエーテルアセタート(PGMEA)またはシクロヘキサノン中に10重量%固形分で配合され、0.2μmのポリ(テトラフルオロエチレン)(PTFE)シリンジフィルタを通して濾過され、シリコンウェハ上に1500rpmでコーティングされ、そして100℃で60秒間ベークされて溶媒を除去し、そしてさらに400℃で60秒間にわたって硬化させられた。硬化した膜は、プラズマサーモ(Plasmatherm)RIE790ツール(Plasma−Therm Co.から)および表4に示された条件を用いてO2またはCF4プラズマを用いてエッチングされた。エッチングデータ(Å/秒単位)が表5に報告される。
Claims (13)
- 式
の1種以上の第1のモノマーと、式Ar−CHO(式中、Arは少なくとも2つの縮合芳香環を有するC10−C30芳香族部分であって、この芳香族部分は場合によっては、C1−C30アルキル、C2−C30アルケニル、C7−C30アラルキル、C6−C30アリール、置換C6−C30アリール、−OR3、−C1−C30アルキレン−OR3、および−C1−C30アルキリデン−OR3の1以上で置換されていてよく、R3はH、C1−C30アルキル、およびC6−C30アリールから選択される)の1種以上の第2のモノマーとを含む組み合わせ物から形成される反応生成物。 - n=0〜4である請求項1に記載の反応生成物。
- 各Rが独立して、C1−C20アルキル、C2−C20アルケニル、C7−C30アラルキル、C6−C30アリール、置換C6−C30アリール、−OR1、−C1−C12アルキレン−OR1、および−C1−C20アルキリデン−OR1から選択される請求項1に記載の反応生成物。
- 第2のモノマーが1以上のヒドロキシルで置換されている、請求項1に記載の反応生成物。
- Arが、2〜5個の縮合芳香環を有するC10−C30芳香族部分である、請求項1に記載の反応生成物。
- 式
の1種以上の第1のモノマーと、式Ar−CHO(式中、Arは少なくとも2つの縮合芳香環を有するC10−C30芳香族部分であって、この芳香族部分は場合によっては、C1−C30アルキル、C2−C30アルケニル、C7−C30アラルキル、C6−C30アリール、置換C6−C30アリール、−OR3、−C1−C30アルキレン−OR3、および−C1−C30アルキリデン−OR3の1以上で置換されていてよく、R3はH、C1−C30アルキル、およびC6−C30アリールから選択される)の1種以上の第2のモノマーとを、酸の存在下で、かつ場合によって溶媒中で反応させることを含む、反応生成物を製造する方法。 - 前記溶媒が極性である請求項6に記載の方法。
- 前記酸がジカルボン酸、鉱酸およびスルホン酸から選択される請求項6に記載の方法。
- 請求項6の方法により製造されるポリマー系反応生成物。
- 請求項1の反応生成物と、有機溶媒と、並びに場合によって、硬化剤、架橋剤および界面活性剤から選択される1種以上の添加剤とを含む組成物。
- 基体上に請求項11の組成物の層を配置し、有機溶媒を除去して反応生成物層を形成し、前記反応生成物層上にフォトレジストの層を配置し、前記フォトレジスト層を化学線にマスクを介して露光し、露光された前記フォトレジスト層を現像してレジストパターンを形成し、および前記パターンを前記反応生成物層に転写して、基体の部分を露出させることを含む、パターン形成された層を形成する方法。
- 前記基体をパターン形成する工程、および次いで前記パターン形成された反応生成物層を除去する工程をさらに含む、請求項11に記載の方法。
- 前記パターン形成された反応生成物層および前記基体の露出した部分の上に共形的なケイ素含有層を配置する工程、前記ケイ素含有層を部分的にエッチングして、前記パターン形成されたポリマー系反応生成物層の頂部表面、および前記基体の部分を露出させる工程をさらに含む、請求項11に記載の方法。
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KR101940655B1 (ko) * | 2016-11-22 | 2019-01-21 | 동우 화인켐 주식회사 | 하드마스크용 조성물 |
US10790146B2 (en) * | 2016-12-05 | 2020-09-29 | Rohm And Haas Electronic Materials Llc | Aromatic resins for underlayers |
US11175581B2 (en) * | 2016-12-05 | 2021-11-16 | Rohm And Haas Electronic Materials Llc | Aromatic resins for underlayers |
CN106946677B (zh) | 2017-04-20 | 2019-07-12 | 深圳市华星光电半导体显示技术有限公司 | 稠环化合物及其应用、电致发光器件及其制备方法 |
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KR20150069557A (ko) | 2015-06-23 |
US9809672B2 (en) | 2017-11-07 |
US20170073453A1 (en) | 2017-03-16 |
CN104710588B (zh) | 2017-04-12 |
TW201538577A (zh) | 2015-10-16 |
KR102313101B1 (ko) | 2021-10-15 |
JP6525373B2 (ja) | 2019-06-05 |
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US9540476B2 (en) | 2017-01-10 |
CN104710588A (zh) | 2015-06-17 |
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