JP2018092170A - 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
- JP2018092170A JP2018092170A JP2017231356A JP2017231356A JP2018092170A JP 2018092170 A JP2018092170 A JP 2018092170A JP 2017231356 A JP2017231356 A JP 2017231356A JP 2017231356 A JP2017231356 A JP 2017231356A JP 2018092170 A JP2018092170 A JP 2018092170A
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- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- layer
- independently
- hydroxyalkyl
- 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
- 229920005989 resin Polymers 0.000 title claims abstract description 105
- 239000011347 resin Substances 0.000 title claims abstract description 105
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 81
- 239000000178 monomer Substances 0.000 claims abstract description 128
- 239000000203 mixture Substances 0.000 claims abstract description 84
- 239000000758 substrate Substances 0.000 claims abstract description 63
- 238000000034 method Methods 0.000 claims abstract description 56
- 229920002120 photoresistant polymer Polymers 0.000 claims abstract description 46
- 229920000412 polyarylene Polymers 0.000 claims abstract description 39
- 239000003960 organic solvent Substances 0.000 claims abstract description 36
- FQQOMPOPYZIROF-UHFFFAOYSA-N cyclopenta-2,4-dien-1-one Chemical compound O=C1C=CC=C1 FQQOMPOPYZIROF-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000000576 coating method Methods 0.000 claims abstract description 16
- 239000000126 substance Substances 0.000 claims abstract description 16
- 239000011248 coating agent Substances 0.000 claims abstract description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 36
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 35
- 229910052710 silicon Inorganic materials 0.000 claims description 35
- 239000010703 silicon Substances 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 28
- 238000011049 filling Methods 0.000 claims description 19
- 239000004065 semiconductor Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 13
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 12
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 10
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 10
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 8
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 6
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 6
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 6
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 6
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 claims description 6
- 125000001725 pyrenyl group Chemical group 0.000 claims description 6
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 5
- 229960002903 benzyl benzoate Drugs 0.000 claims description 5
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims description 5
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 claims description 5
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 238000000059 patterning Methods 0.000 claims description 4
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 claims description 4
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 3
- 125000003336 coronenyl group Chemical group C1(=CC2=CC=C3C=CC4=CC=C5C=CC6=CC=C1C1=C6C5=C4C3=C21)* 0.000 claims description 3
- 229940116333 ethyl lactate Drugs 0.000 claims description 3
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 claims description 3
- XYVQFUJDGOBPQI-UHFFFAOYSA-N Methyl-2-hydoxyisobutyric acid Chemical compound COC(=O)C(C)(C)O XYVQFUJDGOBPQI-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 238000006116 polymerization reaction Methods 0.000 abstract description 4
- 239000010410 layer Substances 0.000 description 143
- 229920000642 polymer Polymers 0.000 description 63
- -1 alkane radicals Chemical class 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 33
- 239000011541 reaction mixture Substances 0.000 description 31
- 239000007787 solid Substances 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 24
- 238000005530 etching Methods 0.000 description 21
- 238000009472 formulation Methods 0.000 description 20
- 238000001723 curing Methods 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
- 125000000304 alkynyl group Chemical group 0.000 description 17
- 238000001914 filtration Methods 0.000 description 17
- 125000005843 halogen group Chemical group 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 235000012431 wafers Nutrition 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 13
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 12
- 238000005227 gel permeation chromatography Methods 0.000 description 11
- 229910052760 oxygen Inorganic materials 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 229910052717 sulfur Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000004528 spin coating Methods 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 239000002318 adhesion promoter Substances 0.000 description 6
- 239000008199 coating composition Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 238000001878 scanning electron micrograph Methods 0.000 description 6
- QGLVWTFUWVTDEQ-UHFFFAOYSA-N 2-chloro-3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1Cl QGLVWTFUWVTDEQ-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 5
- 238000012546 transfer Methods 0.000 description 5
- 238000005698 Diels-Alder reaction Methods 0.000 description 4
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical compound C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 150000001345 alkine derivatives Chemical group 0.000 description 4
- 230000003667 anti-reflective effect Effects 0.000 description 4
- 150000008378 aryl ethers Chemical class 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 239000007810 chemical reaction solvent Substances 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 239000012776 electronic material Substances 0.000 description 4
- 125000004404 heteroalkyl group Chemical group 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- NIEHEMAZEULEKB-UHFFFAOYSA-N ortho-ethylanisole Natural products CCC1=CC=CC=C1OC NIEHEMAZEULEKB-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Chemical group 0.000 description 4
- 238000001020 plasma etching Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- QPXGHGNAEBFULS-UHFFFAOYSA-N (3,5-dibromophenyl) acetate Chemical compound CC(=O)OC1=CC(Br)=CC(Br)=C1 QPXGHGNAEBFULS-UHFFFAOYSA-N 0.000 description 3
- YUOGUVUAZGQYFR-UHFFFAOYSA-N 1,3,5-tris(2-phenylethynyl)benzene Chemical compound C1=CC=CC=C1C#CC1=CC(C#CC=2C=CC=CC=2)=CC(C#CC=2C=CC=CC=2)=C1 YUOGUVUAZGQYFR-UHFFFAOYSA-N 0.000 description 3
- PNXLPYYXCOXPBM-UHFFFAOYSA-N 1,3-diethynylbenzene Chemical compound C#CC1=CC=CC(C#C)=C1 PNXLPYYXCOXPBM-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- MVLGANVFCMOJHR-UHFFFAOYSA-N 1,4-diethynylbenzene Chemical compound C#CC1=CC=C(C#C)C=C1 MVLGANVFCMOJHR-UHFFFAOYSA-N 0.000 description 3
- MXJJMQSKDPNPSX-UHFFFAOYSA-N 1-ethynyl-4-(4-ethynylphenyl)benzene Chemical group C1=CC(C#C)=CC=C1C1=CC=C(C#C)C=C1 MXJJMQSKDPNPSX-UHFFFAOYSA-N 0.000 description 3
- QGISQMYNNUMENK-UHFFFAOYSA-N 6-ethynyl-1-(6-ethynyl-2-hydroxynaphthalen-1-yl)naphthalen-2-ol Chemical compound C#CC1=CC=C2C(C3=C4C=CC(=CC4=CC=C3O)C#C)=C(O)C=CC2=C1 QGISQMYNNUMENK-UHFFFAOYSA-N 0.000 description 3
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 3
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 3
- 229910001424 calcium ion Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- 229910001416 lithium ion Inorganic materials 0.000 description 3
- 229910001425 magnesium ion Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 229910001414 potassium ion Inorganic materials 0.000 description 3
- 239000011241 protective layer Substances 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229910001415 sodium ion Inorganic materials 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000004094 surface-active agent Substances 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
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 2
- ZDRMMTYSQSIGRY-UHFFFAOYSA-N 1,3,5-triethynylbenzene Chemical compound C#CC1=CC(C#C)=CC(C#C)=C1 ZDRMMTYSQSIGRY-UHFFFAOYSA-N 0.000 description 2
- OYEDTTNTNYKSFX-UHFFFAOYSA-N 1,3-bis(2-phenylethynyl)benzene Chemical compound C1=CC=CC=C1C#CC1=CC=CC(C#CC=2C=CC=CC=2)=C1 OYEDTTNTNYKSFX-UHFFFAOYSA-N 0.000 description 2
- FPVSTPLZJLYNMB-UHFFFAOYSA-N 1,4-bis(2-phenylethynyl)benzene Chemical compound C1=CC=CC=C1C#CC1=CC=C(C#CC=2C=CC=CC=2)C=C1 FPVSTPLZJLYNMB-UHFFFAOYSA-N 0.000 description 2
- KJMJERORSUULRM-UHFFFAOYSA-N 1-(2-phenylethynyl)-4-[4-(2-phenylethynyl)phenyl]benzene Chemical group C1=CC=CC=C1C#CC1=CC=C(C=2C=CC(=CC=2)C#CC=2C=CC=CC=2)C=C1 KJMJERORSUULRM-UHFFFAOYSA-N 0.000 description 2
- JTJPCQLJHDCSOK-UHFFFAOYSA-N 1-[1-(2-acetyl-6-bromonaphthalen-1-yl)-6-bromonaphthalen-2-yl]ethanone Chemical compound BrC=1C=C2C=CC(=C(C2=CC=1)C1=C(C=CC2=CC(=CC=C12)Br)C(C)=O)C(C)=O JTJPCQLJHDCSOK-UHFFFAOYSA-N 0.000 description 2
- BLMBNEVGYRXFNA-UHFFFAOYSA-N 1-methoxy-2,3-dimethylbenzene Chemical compound COC1=CC=CC(C)=C1C BLMBNEVGYRXFNA-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- AMOYMEBHYUTMKJ-UHFFFAOYSA-N 2-(2-phenylethoxy)ethylbenzene Chemical compound C=1C=CC=CC=1CCOCCC1=CC=CC=C1 AMOYMEBHYUTMKJ-UHFFFAOYSA-N 0.000 description 2
- IOSGANIYBODQTB-UHFFFAOYSA-N 2-ethynylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C#C IOSGANIYBODQTB-UHFFFAOYSA-N 0.000 description 2
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 2
- CEBKHWWANWSNTI-UHFFFAOYSA-N 2-methylbut-3-yn-2-ol Chemical compound CC(C)(O)C#C CEBKHWWANWSNTI-UHFFFAOYSA-N 0.000 description 2
- XKDCNRXSRQYFSK-UHFFFAOYSA-N 3,5-bis(2-phenylethynyl)phenol Chemical compound C1(=CC=CC=C1)C#CC=1C=C(C=C(C=1)C#CC1=CC=CC=C1)O XKDCNRXSRQYFSK-UHFFFAOYSA-N 0.000 description 2
- XCPGIAPFQBCEAQ-UHFFFAOYSA-N 3,5-diethynylphenol Chemical compound OC1=CC(C#C)=CC(C#C)=C1 XCPGIAPFQBCEAQ-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 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
- 239000004793 Polystyrene Substances 0.000 description 2
- AAQDYYFAFXGBFZ-UHFFFAOYSA-N Tetrahydrofurfuryl acetate Chemical compound CC(=O)OCC1CCCO1 AAQDYYFAFXGBFZ-UHFFFAOYSA-N 0.000 description 2
- DPZVDLFOAZNCBU-UHFFFAOYSA-N Tetrahydrofurfuryl butyrate Chemical compound CCCC(=O)OCC1CCCO1 DPZVDLFOAZNCBU-UHFFFAOYSA-N 0.000 description 2
- FMKCDSXOYLTWBR-UHFFFAOYSA-N Tetrahydrofurfuryl propionate Chemical compound CCC(=O)OCC1CCCO1 FMKCDSXOYLTWBR-UHFFFAOYSA-N 0.000 description 2
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- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- OSWMMVUHYHQYCV-UHFFFAOYSA-N tetrabenzylazanium Chemical compound C=1C=CC=CC=1C[N+](CC=1C=CC=CC=1)(CC=1C=CC=CC=1)CC1=CC=CC=C1 OSWMMVUHYHQYCV-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- CZMILNXHOAKSBR-UHFFFAOYSA-N tetraphenylazanium Chemical compound C1=CC=CC=C1[N+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CZMILNXHOAKSBR-UHFFFAOYSA-N 0.000 description 1
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- MAKDTFFYCIMFQP-UHFFFAOYSA-N titanium tungsten Chemical compound [Ti].[W] MAKDTFFYCIMFQP-UHFFFAOYSA-N 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- H01L21/027—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34
- H01L21/033—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers
- H01L21/0332—Making masks on semiconductor bodies for further photolithographic processing not provided for in group H01L21/18 or H01L21/34 comprising inorganic layers characterised by their composition, e.g. multilayer masks, materials
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Abstract
【解決手段】(a)重合単位として式(1)の第1モノマー
)、ならびに2つ以上のシクロペンタジエノン部分を含む第2モノマーを含むポリアリーレン樹脂と有機溶媒とを含む組成物の層を基板上にコーティングするステップと、(b)有機溶媒を除去して芳香族樹脂層を形成するステップと、(c)フォトレジスト層を芳香族樹脂層上にコーティングするステップと、(d)フォトレジスト層を化学線に対して露出するステップと、(e)現像してレジストパターンを形成するステップと、(f)パターンをポリアリーレン樹脂層に転写して基板の一部を露出するステップと、を含む。
【選択図】なし
Description
各R11は、ハロゲン、C1−6−アルキル、C1−6−ハロアルキル、C1−6−アルコキシ、C1−6−ハロアルコキシ、フェニル、及びフェノキシから独立して選択され、c3は、0〜4の整数であり、d3及びeの各々は、独立して、0〜3の整数であり、各Zは、化学結合、O、S、NR12、PR12、P(=O)R12、C(=O)、CR13R14、及びSiR13R14から独立して選択され、R12、R13、及びR14は、H、C1−4−アルキル、ハロ−C1−4−アルキル、及びフェニルから独立して選択される。xは、1または2であることが好ましく、より好ましくは、1である。yは、0または1であることが好ましく、より好ましくは、1である。好ましくは、各R11は、ハロゲン、C1−4−アルキル、ハロ−C1−4−アルキル、C1−4−アルコキシ、ハロ−C1−4−アルコキシ、及びフェニルから、より好ましくはフルオロ、C1−4−アルキル、フルオロ−C1−4−アルキル、C1−4−アルコキシ、フルオロ−C1−4−アルコキシ、及びフェニルから独立して選択される。c3は、0〜3であることが好ましく、より好ましくは0〜2であり、なおもより好ましくは0または1である。d3及びeの各々は、独立して、0〜2であることが好ましく、より好ましくは、0または1である。式(12)において、d3+e=0〜4であることが好ましく、より好ましくは、0〜2である。各Zは、好ましくは、O、S、NR12、C(=O)、CR13R14、及びSiR13R14から、より好ましくはO、S、C(=O)、及びCR13R14から、なおもより好ましくはO、C(=O)、及びCR13R14から独立して選択される。各R12、R13、及びR14は、H、C1−4−アルキル、フルオロ−C1−4−アルキル、及びフェニルから、より好ましくはH、C1−4−アルキル、フルオロ−C1−2−アルキル、及びフェニル選択されることが好ましい。好ましくは、各Ar4は、式(11)を有している。
Claims (14)
- パターン層を形成するプロセスであって、
(a)(i)重合単位として、式(1)の1つ以上の第1のモノマー
(b)有機溶媒を除去して、芳香族樹脂層を形成するステップと、
(c)フォトレジストの層を、前記芳香族樹脂層上にコーティングするステップと、
(d)前記フォトレジスト層を、マスクを介して、化学線に対して露出するステップと、
(e)前記露出したフォトレジスト層を現像してレジストパターンを形成するステップと、
(f)前記パターンを前記ポリアリーレン樹脂層に転写して、前記基板の一部を露出するステップと、を含む、方法。 - 前記基板にパターン形成するステップと、次いで、前記パターン形成した芳香族樹脂層を除去するステップと、をさらに含む、請求項1に記載の方法。
- ステップ(c)の前に、シリコン含有層を前記芳香族樹脂層上にコーティングするステップをさらに含む、請求項1に記載の方法。
- ステップ(c)の後及びステップ(d)の前に、前記パターンを、前記シリコン含有層に転写するステップをさらに含む、請求項3に記載の方法。
- 前記芳香族樹脂が、重合単位として、式(13)の1つ以上の第3のモノマーをさらに含み、
- f=0である、請求項5に記載の方法。
- R1が、−OH、−C(=O)OR3、−C(=O)N(R4)2、−O−C(=O)R5,−S(=O)2−OR5、及びS(=O)2−N(R4)2から選択される、請求項1に記載の方法。
- R3=H、C1−6−アルキル、C1−6−ヒドロキシアルキル、またはMであり、R4=H、またはC1−6−アルキルであり、R5=H、C1−6−アルキル、−O(C1−6−アルキル)、または−NH(C1−6−アルキル)であり、R7=HまたはC1−6−アルキルである、請求項7に記載の方法。
- R1が、−OH及び−C(=O)OR3から選択される、請求項7に記載の方法。
- 前記1つ以上の第1のモノマーが、式(2)を有し、
- Ar1及びAr2が、フェニル、ナフチル、アントラセニル、フェナントリル、ピレニル、コロネニル、テトラセニル、ペンタセニル、トリフェニレニル、及びペリレニルから独立して選択される、請求項1に記載の方法。
- 前記1つ以上の第2のモノマーが、式(9)の1つ以上のモノマーから選択され、
- 前記1つ以上の有機溶媒が、プロピレングリコールメチルエーテル、酢酸プロピレングリコールメチルエーテル、3−メトキシプロピオン酸メチル、乳酸エチル、酢酸n−ブチル、アニソール、N−メチルピロリドン、ガンマ−ブチロラクトン、エトキシベンゼン、プロピオン酸ベンジル、安息香酸ベンジル、プロピレンカーボネート、2−ヒドロキシイソ酪酸メチル、シクロヘキサノン、及びこれらの混合物から選択される、請求項1に記載の方法。
- ギャップを充填するためのプロセスであって、(a)基板の表面にレリーフ画像を有する半導体基板を提供するステップであって、前記レリーフ画像が、充填される複数のギャップを含む、ステップと、(b)ギャップ充填組成物を前記レリーフ画像に塗布するステップであって、前記ギャップ充填組成物が、(i)重合単位として、式(1)の1つ以上の第1のモノマー、及び2つ以上のシクロペンタジエノン部分を含む1つ以上の第2のモノマーを含む、ポリアリーレン樹脂
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