JP2005241963A - Composition for forming antireflection film and antireflection film - Google Patents
Composition for forming antireflection film and antireflection film Download PDFInfo
- Publication number
- JP2005241963A JP2005241963A JP2004051548A JP2004051548A JP2005241963A JP 2005241963 A JP2005241963 A JP 2005241963A JP 2004051548 A JP2004051548 A JP 2004051548A JP 2004051548 A JP2004051548 A JP 2004051548A JP 2005241963 A JP2005241963 A JP 2005241963A
- Authority
- JP
- Japan
- Prior art keywords
- group
- antireflection film
- fullerene
- composition
- compound
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 84
- -1 fullerene compound Chemical class 0.000 claims abstract description 80
- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical class C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 claims abstract description 59
- 229920000642 polymer Polymers 0.000 claims abstract description 57
- 229910003472 fullerene Inorganic materials 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 23
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 17
- 125000005843 halogen group Chemical group 0.000 claims abstract description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims description 28
- 238000010438 heat treatment Methods 0.000 claims description 15
- 239000011248 coating agent Substances 0.000 claims description 11
- 238000000576 coating method Methods 0.000 claims description 11
- 239000003431 cross linking reagent Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 7
- 239000003999 initiator Substances 0.000 claims description 4
- 230000003667 anti-reflective effect Effects 0.000 claims description 3
- 238000001312 dry etching Methods 0.000 abstract description 7
- 230000000694 effects Effects 0.000 abstract description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 18
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 15
- 238000000034 method Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 13
- 229920005989 resin Polymers 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000000623 heterocyclic group Chemical group 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- 238000005530 etching Methods 0.000 description 10
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- ATLMFJTZZPOKLC-UHFFFAOYSA-N C70 fullerene Chemical group C12=C(C3=C4C5=C67)C8=C9C%10=C%11C%12=C%13C(C%14=C%15C%16=%17)=C%18C%19=C%20C%21=C%22C%23=C%24C%21=C%21C(C=%25%26)=C%20C%18=C%12C%26=C%10C8=C4C=%25C%21=C5C%24=C6C(C4=C56)=C%23C5=C5C%22=C%19C%14=C5C=%17C6=C5C6=C4C7=C3C1=C6C1=C5C%16=C3C%15=C%13C%11=C4C9=C2C1=C34 ATLMFJTZZPOKLC-UHFFFAOYSA-N 0.000 description 9
- 125000003342 alkenyl group Chemical group 0.000 description 9
- 239000000975 dye Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 230000005855 radiation Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000010703 silicon Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 6
- HXGDTGSAIMULJN-UHFFFAOYSA-N acetnaphthylene Natural products C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- 229920003270 Cymel® Polymers 0.000 description 5
- 125000004054 acenaphthylenyl group Chemical group C1(=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000006100 radiation absorber Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 4
- 150000001240 acenaphthylenes Chemical class 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 229920003986 novolac Polymers 0.000 description 4
- 229920001187 thermosetting polymer Polymers 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Chemical group 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000005427 anthranyl group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 238000005227 gel permeation chromatography Methods 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
- 238000001459 lithography Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229920002492 poly(sulfone) Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000570 polyether Chemical group 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000000542 sulfonic acid group Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 229920005992 thermoplastic resin Polymers 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 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
- CLECMSNCZUMKLM-UHFFFAOYSA-N (4-ethenylphenyl)methanol Chemical compound OCC1=CC=C(C=C)C=C1 CLECMSNCZUMKLM-UHFFFAOYSA-N 0.000 description 2
- HHYVKZVPYXHHCG-UHFFFAOYSA-M (7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate;diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1.C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C HHYVKZVPYXHHCG-UHFFFAOYSA-M 0.000 description 2
- FXEDECJAXCCXOU-UHFFFAOYSA-N 1-(2-(diphenylmethoxy)ethyl)-4-(2-(4-azido-3-iodophenyl)ethyl)piperazine Chemical compound C1=C(N=[N+]=[N-])C(I)=CC(CCN2CCN(CCOC(C=3C=CC=CC=3)C=3C=CC=CC=3)CC2)=C1 FXEDECJAXCCXOU-UHFFFAOYSA-N 0.000 description 2
- HNALCILDZDQZGG-UHFFFAOYSA-N 1-(methoxymethyl)acenaphthylene Chemical class C1=CC(C(COC)=C2)=C3C2=CC=CC3=C1 HNALCILDZDQZGG-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- QACHKHNOXGITDA-UHFFFAOYSA-N 3-(methoxymethyl)acenaphthylene Chemical group C1=CC=C2C=CC3=C2C1=CC=C3COC QACHKHNOXGITDA-UHFFFAOYSA-N 0.000 description 2
- VSTHHURIPGNOMC-UHFFFAOYSA-N 4-(methoxymethyl)acenaphthylene Chemical group C1=CC2=CC(COC)=CC(C=C3)=C2C3=C1 VSTHHURIPGNOMC-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- WXYSZTISEJBRHW-UHFFFAOYSA-N 4-[2-[4-[1,1-bis(4-hydroxyphenyl)ethyl]phenyl]propan-2-yl]phenol Chemical compound C=1C=C(C(C)(C=2C=CC(O)=CC=2)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WXYSZTISEJBRHW-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- OKXAGANALYGERX-UHFFFAOYSA-N 5-(methoxymethyl)acenaphthylene Chemical group C1=CC2=CC=CC3=C2C1=CC=C3COC OKXAGANALYGERX-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- RSLNRVYIRDVHLY-UHFFFAOYSA-N Tulobuterol hydrochloride Chemical compound [Cl-].CC(C)(C)[NH2+]CC(O)C1=CC=CC=C1Cl RSLNRVYIRDVHLY-UHFFFAOYSA-N 0.000 description 2
- GWJBEJFEFFWFBI-UHFFFAOYSA-N acenaphthylen-1-ylmethanol Chemical class C1=CC(C(CO)=C2)=C3C2=CC=CC3=C1 GWJBEJFEFFWFBI-UHFFFAOYSA-N 0.000 description 2
- MOASFWJQSIPNPT-UHFFFAOYSA-N acenaphthylen-1-ylmethyl acetate Chemical class C1=CC(C(COC(=O)C)=C2)=C3C2=CC=CC3=C1 MOASFWJQSIPNPT-UHFFFAOYSA-N 0.000 description 2
- LCGDCBVLETZTPI-UHFFFAOYSA-N acenaphthylen-3-ylmethanol Chemical group C1=CC=C2C=CC3=C2C1=CC=C3CO LCGDCBVLETZTPI-UHFFFAOYSA-N 0.000 description 2
- DGLWWNBDEQAEPZ-UHFFFAOYSA-N acenaphthylen-3-ylmethyl acetate Chemical group C1=CC=C2C=CC3=C2C1=CC=C3COC(=O)C DGLWWNBDEQAEPZ-UHFFFAOYSA-N 0.000 description 2
- LZQPTSRHLOQKSZ-UHFFFAOYSA-N acenaphthylen-4-ylmethanol Chemical group C1=CC2=CC(CO)=CC(C=C3)=C2C3=C1 LZQPTSRHLOQKSZ-UHFFFAOYSA-N 0.000 description 2
- KBSNYVVAXWORRO-UHFFFAOYSA-N acenaphthylen-5-ylmethanol Chemical group C1=CC2=CC=CC3=C2C1=CC=C3CO KBSNYVVAXWORRO-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000008360 acrylonitriles Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 238000001241 arc-discharge method Methods 0.000 description 2
- MDUKBVGQQFOMPC-UHFFFAOYSA-M bis(4-tert-butylphenyl)iodanium;(7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonate Chemical compound C1CC2(CS([O-])(=O)=O)C(=O)CC1C2(C)C.C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 MDUKBVGQQFOMPC-UHFFFAOYSA-M 0.000 description 2
- DJBAOXYQCAKLPH-UHFFFAOYSA-M bis(4-tert-butylphenyl)iodanium;1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F.C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 DJBAOXYQCAKLPH-UHFFFAOYSA-M 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 description 2
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
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- 230000005251 gamma ray Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical compound N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000003903 lactic acid esters Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-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
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 1
- LYLUAHKXJUQFDG-UHFFFAOYSA-N methyl 3-methoxy-2-methylpropanoate Chemical compound COCC(C)C(=O)OC LYLUAHKXJUQFDG-UHFFFAOYSA-N 0.000 description 1
- WEBFLHSTQYJFHU-UHFFFAOYSA-M methyl [4-(thiolan-1-ium-1-yl)naphthalen-1-yl] carbonate;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C12=CC=CC=C2C(OC(=O)OC)=CC=C1[S+]1CCCC1 WEBFLHSTQYJFHU-UHFFFAOYSA-M 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229940017144 n-butyl lactate Drugs 0.000 description 1
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical class C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- LABYRQOOPPZWDG-UHFFFAOYSA-M naphthalene-1-sulfonate;triphenylsulfanium Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 LABYRQOOPPZWDG-UHFFFAOYSA-M 0.000 description 1
- FNJACQKXCBUZGH-UHFFFAOYSA-N naphthalene-1-sulfonic acid hydroiodide Chemical compound OS(C1=CC=CC2=CC=CC=C12)(=O)=O.I FNJACQKXCBUZGH-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadec-1-ene Chemical compound CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229920002114 octoxynol-9 Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- QYZLKGVUSQXAMU-UHFFFAOYSA-N penta-1,4-diene Chemical compound C=CCC=C QYZLKGVUSQXAMU-UHFFFAOYSA-N 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920000141 poly(maleic anhydride) Polymers 0.000 description 1
- 229920003214 poly(methacrylonitrile) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920013639 polyalphaolefin Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920002577 polybenzoxazole Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
- VMBJJCDVORDOCF-UHFFFAOYSA-N prop-2-enyl 2-chloroacetate Chemical compound ClCC(=O)OCC=C VMBJJCDVORDOCF-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux 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
- BZLCXASSRGMESX-UHFFFAOYSA-N silylmethyl prop-2-enoate Chemical compound C(C=C)(=O)OC[SiH3] BZLCXASSRGMESX-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- UACVJSDAGHJPNP-UHFFFAOYSA-M tert-butyl [4-(thiolan-1-ium-1-yl)naphthalen-1-yl] carbonate;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C12=CC=CC=C2C(OC(=O)OC(C)(C)C)=CC=C1[S+]1CCCC1 UACVJSDAGHJPNP-UHFFFAOYSA-M 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
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- UWIVZLWKBOZJFG-UHFFFAOYSA-N thiolan-1-ium trifluoromethanesulfonate Chemical compound C1CC[SH+]C1.[O-]S(=O)(=O)C(F)(F)F UWIVZLWKBOZJFG-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- FAYMLNNRGCYLSR-UHFFFAOYSA-M triphenylsulfonium triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 FAYMLNNRGCYLSR-UHFFFAOYSA-M 0.000 description 1
- WQJQOUPTWCFRMM-UHFFFAOYSA-N tungsten disilicide Chemical compound [Si]#[W]#[Si] WQJQOUPTWCFRMM-UHFFFAOYSA-N 0.000 description 1
- 229910021342 tungsten silicide Inorganic materials 0.000 description 1
- 229920001567 vinyl ester resin Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y20/00—Nanooptics, e.g. quantum optics or photonic crystals
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- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Nanotechnology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Biophysics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Composite Materials (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Materials For Photolithography (AREA)
- Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
Abstract
Description
本発明は、各種の放射線を用いるリソグラフィープロセスにおける微細加工に有用で、特に集積回路素子の製造に好適な反射防止膜形成用組成物、およびこの組成物を用いて形成された反射防止膜に関する。 The present invention relates to a composition for forming an antireflection film that is useful for microfabrication in a lithography process using various types of radiation, and is particularly suitable for manufacturing integrated circuit elements, and an antireflection film formed using this composition.
集積回路素子の製造方法において、より高い集積度を得るためにリソグラフィープロセスにおける加工サイズの微細化が進んでいる。このリソグラフィープロセスにおいて、液状のレジスト用組成物を基板上に塗布し、縮小投影露光装置(ステッパー)によってマスクパターンを転写し、適当な現像液で現像することによって、所望のパターンを得ている。しかしながら、このプロセスに用いられる反射率の高いアルミニウム、アルミニウム−シリコン合金、アルミニウム−シリコン−銅合金、ポリシリコン、タングステンシリサイドなどの基板は、照射した放射線をその表面で反射する。その影響で、レジストパターンにハレーションが生じ、微細なレジストパターンが正確に再現できないという問題があった。 In the manufacturing method of an integrated circuit element, in order to obtain a higher degree of integration, the processing size in the lithography process is miniaturized. In this lithography process, a liquid resist composition is applied onto a substrate, a mask pattern is transferred by a reduction projection exposure apparatus (stepper), and developed with an appropriate developer to obtain a desired pattern. However, highly reflective substrates such as aluminum, aluminum-silicon alloys, aluminum-silicon-copper alloys, polysilicon, tungsten silicide, etc. used in this process reflect the irradiated radiation at the surface. As a result, there is a problem that halation occurs in the resist pattern and a fine resist pattern cannot be accurately reproduced.
この問題を解決するため、基板上に形成すべきレジスト膜の下に、基板から反射した放射線を吸収する性質のある反射防止膜を設けることが提案されている。このような反射防止膜としては、真空蒸着、CVD、スパッタリングなどの方法により形成される、チタン膜、二酸化チタン膜、チッ化チタン膜、酸化クロム膜、カーボン膜、α−シリコン膜などの無機膜が知られているが、これらの無機系反射防止膜は導電性を有するため、集積回路の製造には使用できなかったり、反射防止膜の形成に真空蒸着装置、CVD装置、スパッタリング装置などの特別な装置を必要とするなどの欠点があった。この無機系反射防止膜の欠点を解決するために、ポリアミド酸(共)重合体またはポリスルホン(共)重合体と染料とからなる有機系反射防止膜が提案されている(特許文献1)。この反射防止膜は導電性が無く、この反射防止膜を構成している組成物は適当な溶剤に溶解するため、特別な装置を必要せずに、レジストと同様に溶液の状態で基板上に塗布できる。 In order to solve this problem, it has been proposed to provide an antireflection film having a property of absorbing radiation reflected from the substrate under the resist film to be formed on the substrate. As such an antireflection film, an inorganic film such as a titanium film, a titanium dioxide film, a titanium nitride film, a chromium oxide film, a carbon film, or an α-silicon film formed by a method such as vacuum deposition, CVD, or sputtering. However, since these inorganic antireflection films have electrical conductivity, they cannot be used in the production of integrated circuits, or special anti-reflection films such as vacuum deposition equipment, CVD equipment, and sputtering equipment are used to form antireflection films. There were drawbacks such as requiring a simple device. In order to solve the disadvantages of this inorganic antireflection film, an organic antireflection film comprising a polyamic acid (co) polymer or polysulfone (co) polymer and a dye has been proposed (Patent Document 1). This antireflection film has no electrical conductivity, and the composition constituting the antireflection film is dissolved in an appropriate solvent. Therefore, a special apparatus is not required and the solution is formed on the substrate in the same state as the resist. Can be applied.
しかしながら、ポリアミド酸(共)重合体またはポリスルホン(共)重合体と染料とからなる反射防止膜は、染料の添加量が制約されるためにハレーションや定在波を十分に防止できず、またレジストと僅かながら混じり合う(これを「インターミキシング」という)ため、抜け不良、裾引きといったレジストパターン断面形状(パターンプロファイル)の劣化を招くという問題があった。 However, an antireflection film comprising a polyamic acid (co) polymer or a polysulfone (co) polymer and a dye cannot sufficiently prevent halation and standing waves because the amount of the dye added is limited. However, there is a problem that the resist pattern cross-sectional shape (pattern profile) such as omission failure and tailing is deteriorated.
一方、熱酸化ノボラック樹脂を反射防止膜に使用すると、前述したような問題点をかなり解決できることが知られているが、今後の更なる微細なエッチング加工における、絶縁膜にパターンを転写する際のエッチング耐性不足により発生する寸法変換差の課題は十分に解決されていない。 On the other hand, it is known that the use of a thermally oxidized novolac resin as an antireflection film can considerably solve the above-mentioned problems. However, when a pattern is transferred to an insulating film in further fine etching processing in the future. The problem of dimensional conversion differences caused by insufficient etching resistance has not been sufficiently solved.
そこで、このような従来技術における問題点を解決するための改善された反射防止膜、およびこのような反射防止膜の形成において特に有用な重合体の開発が望まれていた。
本発明は、上記のような従来技術に伴う問題を解決しようとするものであって、ドライエッチング耐性に優れ、反射防止効果が高く、インターミキシングを生じることがなく、
解像度および精度などに優れたレジストパターンを形成しうる反射防止膜形成用組成物、およびこの組成物を用いて形成された反射防止膜を提供することを課題としている。
The present invention is intended to solve the problems associated with the prior art as described above, is excellent in dry etching resistance, has a high antireflection effect, and does not cause intermixing.
An object of the present invention is to provide a composition for forming an antireflection film capable of forming a resist pattern excellent in resolution and accuracy, and an antireflection film formed using this composition.
本発明者は、上記問題点を解決すべく鋭意研究し、ビニル基を含有する化合物とフラーレン化合物とから得られる重合体を反射防止膜に使用することにより、従来の塗布型下層反射防止膜と比較してドライエッチング耐性に優れ、エキシマレーザー光に対して高い吸光度を有する反射防止膜が得られることを見出し、本発明を完成するに至った。 The present inventor has eagerly studied to solve the above problems, and uses a polymer obtained from a vinyl group-containing compound and a fullerene compound as an antireflection film, thereby providing a conventional coating-type lower antireflection film and As a result, it was found that an antireflection film having excellent dry etching resistance and high absorbance with respect to excimer laser light was obtained, and the present invention was completed.
すなわち、本発明に係る反射防止膜形成用組成物は、
下記式(1)で表される繰り返し単位(a−1)とフラーレン構造を有する繰り返し単位(b)とを有する重合体を含有することを特徴としている。
That is, the composition for forming an antireflection film according to the present invention is
It contains a polymer having a repeating unit (a-1) represented by the following formula (1) and a repeating unit (b) having a fullerene structure.
式(1)において、R1は水素原子またはフッ素原子を示し、R2およびR3はそれぞれ
独立に水素原子、フッ素原子または1価の基を示し、R4はハロゲン原子または1価の基
を示す。
In the formula (1), R 1 represents a hydrogen atom or a fluorine atom, R 2 and R 3 each independently represent a hydrogen atom, a fluorine atom or a monovalent group, and R 4 represents a halogen atom or a monovalent group. Show.
また、本発明に係る反射防止膜形成用組成物は、
下記式(2)で表される繰り返し単位(a−2)とフラーレン構造を有する繰り返し単位(b)とを有する重合体を含有することを特徴としている。
In addition, the composition for forming an antireflection film according to the present invention comprises:
It is characterized by containing a polymer having a repeating unit (a-2) represented by the following formula (2) and a repeating unit (b) having a fullerene structure.
式(2)において、R5、R6およびR7はそれぞれ独立に水素原子、ハロゲン原子また
は1価の基を示す。
In the formula (2), R 5 , R 6 and R 7 each independently represent a hydrogen atom, a halogen atom or a monovalent group.
さらに、本発明に係る反射防止膜形成用組成物は、
下記式(3)で表される少なくとも1種の化合物(A−1)または下記式(4)で表される少なくとも1種の化合物(A−2)と、フラーレンおよびフラーレン誘導体からなる群から選択される少なくとも1種のフラーレン化合物(B)とを混合後、ラジカル開始剤存在下で加熱して得られる重合体を含有することを特徴としている。
Furthermore, the composition for forming an antireflection film according to the present invention comprises:
Selected from the group consisting of at least one compound (A-1) represented by the following formula (3) or at least one compound (A-2) represented by the following formula (4), fullerene and a fullerene derivative It is characterized by containing a polymer obtained by mixing at least one fullerene compound (B) and heating in the presence of a radical initiator.
式(3)において、R1は水素原子またはフッ素原子を示し、R2およびR3はそれぞれ
独立に水素原子、フッ素原子または1価の基を示し、R4はハロゲン原子または1価の基
を示す。
In the formula (3), R 1 represents a hydrogen atom or a fluorine atom, R 2 and R 3 each independently represent a hydrogen atom, a fluorine atom or a monovalent group, and R 4 represents a halogen atom or a monovalent group. Show.
式(4)において、R5、R6およびR7はそれぞれ独立に水素原子、ハロゲン原子また
は1価の基を示す。
In the formula (4), R 5 , R 6 and R 7 each independently represent a hydrogen atom, a halogen atom or a monovalent group.
前記反射防止膜形成用組成物は、架橋剤(C)をさらに含有することが好ましく、酸発生剤(D)をさらに含有することも好ましい。 The antireflection film-forming composition preferably further contains a crosslinking agent (C), and preferably further contains an acid generator (D).
本発明に係る反射防止膜は、上記組成物を用いて形成した塗膜を150〜350℃で加熱することにより形成されたことを特徴としている。 The antireflection film according to the present invention is formed by heating a coating film formed using the above composition at 150 to 350 ° C.
本発明に係る反射防止膜形成用組成物は、ドライエッチング耐性に優れ、反射防止効果が高く、かつレジストとインターミキシングを生じることのない反射防止膜を形成することができる。本発明に係る反射防止膜は、ポジ型およびネガ型レジストと協働して、解像度、精度などに優れたレジストパターンを形成することができる。 The composition for forming an antireflection film according to the present invention can form an antireflection film that has excellent dry etching resistance, a high antireflection effect, and does not cause intermixing with a resist. The antireflection film according to the present invention can form a resist pattern having excellent resolution and accuracy in cooperation with positive and negative resists.
〔反射防止膜形成用組成物〕
本発明に係る反射防止膜形成用組成物は、ビニル基を有する特定の化合物とフラーレン化合物とを混合した後、加熱して得られる重合体を含有する。
[Composition for forming antireflection film]
The composition for forming an antireflective film according to the present invention contains a polymer obtained by mixing a specific compound having a vinyl group and a fullerene compound and then heating.
<ビニル基を有する化合物(A)>
<ビニル基を有する化合物(A−1)>
本発明に用いられるビニル基を有する化合物(A−1)(以下、単に「化合物(A−1)」という)は、下記式(3)で表される化合物である。
<Compound having vinyl group (A)>
<Compound having vinyl group (A-1)>
The compound (A-1) (hereinafter simply referred to as “compound (A-1)”) having a vinyl group used in the present invention is a compound represented by the following formula (3).
上記式(3)において、R1は水素原子またはフッ素原子を示し、R2およびR3はそれ
ぞれ独立に水素原子、フッ素原子または1価の基を示し、R4はハロゲン原子または1価
の基を示す。
In the above formula (3), R 1 represents a hydrogen atom or a fluorine atom, R 2 and R 3 each independently represent a hydrogen atom, a fluorine atom or a monovalent group, and R 4 represents a halogen atom or a monovalent group. Indicates.
R2およびR3における1価の基としては炭素数1〜20の基が好ましく、具体的には、アルキル基、アルケニル基、アシル基、シアノ基、エステル基、ヒドロキシル基、メルカプト基、アミノ基、カルボキシル基、スルホン酸基、フェニル基、ナフチル基、アントラニル基;アルケニル基、フェニル基、ナフチル基、アントラニル基をハロゲン原子、ヒドロキシル基、メルカプト基、カルボキシル基、ニトロ基、スルホン酸基、ヒドロキシメチル基、メトキシメチル基、エトキシメチル基などから選ばれる少なくとも1つの原子または置換基で置換された基を挙げることができる。 The monovalent group in R 2 and R 3 is preferably a group having 1 to 20 carbon atoms, specifically, an alkyl group, an alkenyl group, an acyl group, a cyano group, an ester group, a hydroxyl group, a mercapto group, an amino group. , Carboxyl group, sulfonic acid group, phenyl group, naphthyl group, anthranyl group; alkenyl group, phenyl group, naphthyl group, anthranyl group as halogen atom, hydroxyl group, mercapto group, carboxyl group, nitro group, sulfonic acid group, hydroxymethyl And a group substituted with at least one atom or substituent selected from a group, a methoxymethyl group, an ethoxymethyl group, and the like.
アルキル基としては、炭素数1〜10の直鎖状または分岐状のアルキル基が好ましく、さらに好ましくは、メチル基、エチル基、n−プロピル基、i−プロピル基、n−ブチル基、i−ブチル基、sec−ブチル基、t−ブチル基などを挙げることができる。 The alkyl group is preferably a linear or branched alkyl group having 1 to 10 carbon atoms, and more preferably a methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i- A butyl group, a sec-butyl group, a t-butyl group, etc. can be mentioned.
アルケニル基としては、炭素数2〜6の直鎖状または分岐状のアルケニル基が好ましく、さらに好ましくは、ビニル基、アリル基、メタクリル基、1−ブテニル基、2−ブテニル基などを挙げることができる。 The alkenyl group is preferably a linear or branched alkenyl group having 2 to 6 carbon atoms, more preferably a vinyl group, an allyl group, a methacryl group, a 1-butenyl group, a 2-butenyl group, or the like. it can.
アシル基としては、炭素数2〜6の脂肪族または芳香族のアシル基が好ましく、さらに好ましくは、アセチル基、プロピオニル基、ブチリル基、ベンゾイル基などを挙げることができる。 The acyl group is preferably an aliphatic or aromatic acyl group having 2 to 6 carbon atoms, and more preferably an acetyl group, a propionyl group, a butyryl group, a benzoyl group, and the like.
エステル基としては、炭素数2〜20の脂肪族または芳香族のエステル基が好ましく、さらに好ましくは、メトキシカルボニル基、エトキシカルボニル基、ブトキシカルボニル基、i−ブトキシカルボニル基、tert−ブトキシカルボニル基、フェノキシカルボニル基、ベンジロキシカルボニル基などを挙げることができる。 The ester group is preferably an aliphatic or aromatic ester group having 2 to 20 carbon atoms, more preferably a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group, an i-butoxycarbonyl group, a tert-butoxycarbonyl group, A phenoxycarbonyl group, a benzyloxycarbonyl group, etc. can be mentioned.
R4におけるハロゲン原子としては、たとえば、フッ素原子、臭素原子、塩素原子、ヨ
ウ素原子などを挙げることができる。
Examples of the halogen atom for R 4 include a fluorine atom, a bromine atom, a chlorine atom, and an iodine atom.
R4における1価の基としては、たとえば、上記R2およびR3における1価の基で例示
したものと同様の基を挙げることができる。
Examples of the monovalent group in R 4 include the same groups as those exemplified for the monovalent group in R 2 and R 3 .
上記式(3)において、R1としては、特に、水素原子が好ましい。また、R2およびR3としては、それぞれ独立に、水素原子、フッ素原子、メチル基、エチル基、メトキシカ
ルボニル基、シアノ基、フェニル基などが好ましい。R4としては、メチル基、エチル基
、シアノ基、アミノ基、メトキシカルボニル基、エトキシカルボニル基、tert−ブトキシカルボニル基、メチルカルボオキシ基、フェニル基、ナフチル基、アントラニル基、ヒドロキシメチルフェニル基、ヒドロキシメチルナフチル基、メトキシメチルフェニル基、メトキシメチルナフチル基などが好ましい。
In the above formula (3), R 1 is particularly preferably a hydrogen atom. R 2 and R 3 are each independently preferably a hydrogen atom, a fluorine atom, a methyl group, an ethyl group, a methoxycarbonyl group, a cyano group, a phenyl group, or the like. R 4 includes methyl group, ethyl group, cyano group, amino group, methoxycarbonyl group, ethoxycarbonyl group, tert-butoxycarbonyl group, methylcarbooxy group, phenyl group, naphthyl group, anthranyl group, hydroxymethylphenyl group, A hydroxymethylnaphthyl group, a methoxymethylphenyl group, a methoxymethylnaphthyl group and the like are preferable.
上記式(3)で表される具体的な化合物としては、たとえば、
スチレン、α−メチルスチレン、2−メチルスチレン、3−メチルスチレン、4−メチルスチレン、4−ヒドロキシメチルスチレン、3−ヒドロキシメチルスチレン、4−メトキシメチルスチレン、3−メトキシメチルスチレン、1−ビニルナフタレン、2−ビニルナフタレン、1−ビニル−4−ヒドロキシメチルナフタレン、1−ビニル−5−ヒドロキシメチルナフタレン、1−ビニル−6−ヒドロキシメチルナフタレン、2−ビニル−4−ヒドロキシメチルナフタレン、2−ビニル−6−ヒドロキシメチルナフタレン、9−ビニルアントラセン、9−ビニルカルバゾールなどの芳香族ビニル化合物;
酢酸ビニル、プロピオン酸ビニル、カプロン酸ビニルなどのビニルエステル化合物;
(メタ)アクリロニトリル、α−クロロアクリロニトリル、シアン化ビニリデンなどのシアン化ビニル化合物;
メチル(メタ)アクリレート、エチル(メタ)アクリレート、n−プロピル(メタ)アクリレート、i−プロピル(メタ)アクリレート、n−ブチル(メタ)アクリレート、t−ブチル(メタ)アクリレート、グリシジル(メタ)アクリレートなどの不飽和カルボン酸エステル化合物;
エチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、(メタ)アクリル酸ビニル、ジメチル・ビニル・(メタ)アクリロイルオキシメチルシランなどの不飽和基含有不飽和カルボン酸エステル化合物;
2−クロロエチルビニルエーテル、クロロ酢酸ビニル、クロロ酢酸アリルなどのハロゲン含有ビニル化合物;
2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、(メタ)アリルアルコールなどの水酸基含有ビニル化合物;
(メタ)アクリルアミド、クロトン酸アミドなどのアミド基含有ビニル化合物;
コハク酸モノ〔2−(メタ)アクリロイルオキシエチル〕、マレイン酸モノ〔2−(メタ)アクリロイルオキシエチル〕、フタル酸モノ〔2−(メタ)アクリロイルオキシエチル〕、イタコン酸ジメチル、イタコン酸ジエチル、マレイン酸ジメチル、マレイン酸ジエチルなどのカルボキシル基含有ビニル化合物;
ビニルアミン、アリルアミンなどのアミン含有ビニル化合物;
クロロトリフルオロエチレン、2,2,2−トリフルオロエチル(メタ)アクリレート、2,2,3,3,3−ペンタフルオロプロピル(メタ)アクリレート、2−(パーフルオロブチル)エチル(メタ)アクリレート、2−(パーフルオロヘキシル)エチル(メタ)アクリレートなどの含フッ素ビニル化合物などが挙げられる。
As a specific compound represented by the above formula (3), for example,
Styrene, α-methylstyrene, 2-methylstyrene, 3-methylstyrene, 4-methylstyrene, 4-hydroxymethylstyrene, 3-hydroxymethylstyrene, 4-methoxymethylstyrene, 3-methoxymethylstyrene, 1-vinylnaphthalene 2-vinylnaphthalene, 1-vinyl-4-hydroxymethylnaphthalene, 1-vinyl-5-hydroxymethylnaphthalene, 1-vinyl-6-hydroxymethylnaphthalene, 2-vinyl-4-hydroxymethylnaphthalene, 2-vinyl- Aromatic vinyl compounds such as 6-hydroxymethylnaphthalene, 9-vinylanthracene and 9-vinylcarbazole;
Vinyl ester compounds such as vinyl acetate, vinyl propionate and vinyl caproate;
Vinyl cyanide compounds such as (meth) acrylonitrile, α-chloroacrylonitrile, vinylidene cyanide;
Methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, i-propyl (meth) acrylate, n-butyl (meth) acrylate, t-butyl (meth) acrylate, glycidyl (meth) acrylate, etc. An unsaturated carboxylic acid ester compound of
Unsaturated group-containing unsaturated carboxylic acid ester compounds such as ethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, vinyl (meth) acrylate, dimethyl vinyl (meth) acryloyloxymethylsilane;
Halogen-containing vinyl compounds such as 2-chloroethyl vinyl ether, vinyl chloroacetate and allyl chloroacetate;
Hydroxyl group-containing vinyl compounds such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate and (meth) allyl alcohol;
Amide group-containing vinyl compounds such as (meth) acrylamide and crotonic acid amide;
Succinic acid mono [2- (meth) acryloyloxyethyl], maleic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (meth) acryloyloxyethyl], dimethyl itaconate, diethyl itaconate, Carboxyl group-containing vinyl compounds such as dimethyl maleate and diethyl maleate;
Amine-containing vinyl compounds such as vinylamine and allylamine;
Chlorotrifluoroethylene, 2,2,2-trifluoroethyl (meth) acrylate, 2,2,3,3,3-pentafluoropropyl (meth) acrylate, 2- (perfluorobutyl) ethyl (meth) acrylate, Examples thereof include fluorine-containing vinyl compounds such as 2- (perfluorohexyl) ethyl (meth) acrylate.
上記化合物(A−1)は、単独でまたは2種以上を混合して使用することができる。 The said compound (A-1) can be used individually or in mixture of 2 or more types.
<ビニル基を有する化合物(A−2)>
本発明に用いられるビニル基を有する化合物(A−2)(以下、単に「化合物(A−2)」という)は、下記式(4)で表される化合物である。
<Compound having vinyl group (A-2)>
The compound (A-2) having a vinyl group used in the present invention (hereinafter simply referred to as “compound (A-2)”) is a compound represented by the following formula (4).
上記式(4)において、R5、R6およびR7はそれぞれ独立に水素原子、ハロゲン原子
または1価の基を示す。
In the above formula (4), R 5 , R 6 and R 7 each independently represent a hydrogen atom, a halogen atom or a monovalent group.
ハロゲン原子として、好ましくは、フッ素、塩素、臭素を挙げることができる。 Preferred examples of the halogen atom include fluorine, chlorine, and bromine.
1価の基としては、たとえば、アルキル基、アルケニル基、ニトロ基、アミノ基、ヒドロキシル基、フェニル基、アシル基、カルボキシル基、スルホン酸基、メルカプト基などを挙げることができる。 Examples of the monovalent group include an alkyl group, an alkenyl group, a nitro group, an amino group, a hydroxyl group, a phenyl group, an acyl group, a carboxyl group, a sulfonic acid group, and a mercapto group.
アルキル基としては、炭素原子数1〜6の直鎖状または分岐鎖状アルキル基が好ましく、たとえば、メチル、エチル、プロピル、イソプロピル、ブチル、イソブチル、tert−ブチルなどが挙げられる。 The alkyl group is preferably a linear or branched alkyl group having 1 to 6 carbon atoms, and examples thereof include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl and the like.
アルケニル基としては、炭素原子数2〜6の直鎖状または分岐鎖状アルケニル基が好ましく、たとえば、ビニル、アリルなどが挙げられる。 The alkenyl group is preferably a linear or branched alkenyl group having 2 to 6 carbon atoms, and examples thereof include vinyl and allyl.
アシル基としては、炭素原子数1〜6の脂肪族または芳香族アシル基が好ましく、たとえばアセチル基などが挙げられる。 The acyl group is preferably an aliphatic or aromatic acyl group having 1 to 6 carbon atoms, and examples thereof include an acetyl group.
アミノ基としては、第一級アミノ基が好ましい。 As the amino group, a primary amino group is preferable.
上記式(4)で表される具体的な化合物(アセナフチレン類)としては、たとえば、アセナフチレン、ヒドロキシメチルアセナフチレン類、アセトキシメチルアセナフチレン類、メトキシメチルアセナフチレン類が挙げられる。 Specific compounds (acenaphthylenes) represented by the above formula (4) include, for example, acenaphthylene, hydroxymethyl acenaphthylenes, acetoxymethyl acenaphthylenes, and methoxymethyl acenaphthylenes.
ヒドロキシメチルアセナフチレン類としては、3−ヒドロキシメチルアセナフチレン、4−ヒドロキシメチルアセナフチレン、5−ヒドロキシメチルアセナフチレン、1−メチル−3−ヒドロキシメチルアセナフチレン、1−メチル−4−ヒドロキシメチルアセナフチレン、1−メチル−5−ヒドロキシメチルアセナフチレン、1−メチル−6−ヒドロキシメチルアセナフチレン、1−メチル−7−ヒドロキシメチルアセナフチレン、1−メチル−8−ヒドロキシメチルアセナフチレン、1,2−ジメチル−3−ヒドロキシメチルアセナフチレン、1,2−ジメチル−4−ヒドロキシメチルアセナフチレン、1,2−ジメチル−5−ヒドロキシメチルアセナフチレン、1−フェニル−3−ヒドロキシメチルアセナフチレン、1−フェニル−4−ヒドロキシメチルアセナフチレン、1−フェニル−5−ヒドロキシメチルアセナフチレン、1−フェニル−6−ヒドロキシメチルアセナフチレン、1−フェニル−7−ヒドロキシメチルアセナフチレン、1−フェニル−8−ヒドロキシ
メチルアセナフチレン、1,2−ジフェニル−3−ヒドロキシメチルアセナフチレン、1,2−ジフェニル−4−ヒドロキシメチルアセナフチレン、1,2−ジフェニル−5−ヒドロキシメチルアセナフチレンなどが挙げられる。
Examples of hydroxymethyl acenaphthylenes include 3-hydroxymethyl acenaphthylene, 4-hydroxymethyl acenaphthylene, 5-hydroxymethyl acenaphthylene, 1-methyl-3-hydroxymethyl acenaphthylene, 1-methyl-4. -Hydroxymethylacenaphthylene, 1-methyl-5-hydroxymethylacenaphthylene, 1-methyl-6-hydroxymethylacenaphthylene, 1-methyl-7-hydroxymethylacenaphthylene, 1-methyl-8-hydroxy Methyl acenaphthylene, 1,2-dimethyl-3-hydroxymethyl acenaphthylene, 1,2-dimethyl-4-hydroxymethyl acenaphthylene, 1,2-dimethyl-5-hydroxymethyl acenaphthylene, 1-phenyl -3-hydroxymethylacenaphthylene, 1-phenyl-4 Hydroxymethylacenaphthylene, 1-phenyl-5-hydroxymethylacenaphthylene, 1-phenyl-6-hydroxymethylacenaphthylene, 1-phenyl-7-hydroxymethylacenaphthylene, 1-phenyl-8-hydroxymethyl Examples include acenaphthylene, 1,2-diphenyl-3-hydroxymethylacenaphthylene, 1,2-diphenyl-4-hydroxymethylacenaphthylene, 1,2-diphenyl-5-hydroxymethylacenaphthylene, and the like.
アセトキシメチルアセナフチレン類としては、3−アセトキシメチルアセナフチレン、4−アセトキシメチルアセナフチレン、5−アセトキシメチルアセナフチレン、1−メチル−3−アセトキシメチルアセナフチレン、1−メチル−4−アセトキシメチルアセナフチレン、1−メチル−5−アセトキシメチルアセナフチレン、1−メチル−6−アセトキシメチルアセナフチレン、1−メチル−7−アセトキシメチルアセナフチレン、1−メチル−8−アセトキシメチルアセナフチレン、1,2−ジメチル−3−アセトキシメチルアセナフチレン、1,2−ジメチル−4−アセトキシメチルアセナフチレン、1,2−ジメチル−5−アセトキシメチルアセナフチレン、1−フェニル−3−アセトキシメチルアセナフチレン、1−フェニル−4−アセトキシメチルアセナフチレン、1−フェニル−5−アセトキシメチルアセナフチレン、1−フェニル−6−アセトキシメチルアセナフチレン、1−フェニル−7−アセトキシメチルアセナフチレン、1−フェニル−8−アセトキシメチルアセナフチレン、1,2−ジフェニル−3−アセトキシメチルアセナフチレン、1,2−ジフェニル−4−アセトキシメチルアセナフチレン、1,2−ジフェニル−5−アセトキシメチルアセナフチレンなどが挙げられる。 Examples of acetoxymethyl acenaphthylenes include 3-acetoxymethyl acenaphthylene, 4-acetoxymethyl acenaphthylene, 5-acetoxymethyl acenaphthylene, 1-methyl-3-acetoxymethyl acenaphthylene, 1-methyl-4 -Acetoxymethyl acenaphthylene, 1-methyl-5-acetoxymethyl acenaphthylene, 1-methyl-6-acetoxymethyl acenaphthylene, 1-methyl-7-acetoxymethyl acenaphthylene, 1-methyl-8-acetoxy Methyl acenaphthylene, 1,2-dimethyl-3-acetoxymethyl acenaphthylene, 1,2-dimethyl-4-acetoxymethyl acenaphthylene, 1,2-dimethyl-5-acetoxymethyl acenaphthylene, 1-phenyl -3-Acetoxymethylacenaphthylene, 1-phenyl-4 Acetoxymethyl acenaphthylene, 1-phenyl-5-acetoxymethyl acenaphthylene, 1-phenyl-6-acetoxymethyl acenaphthylene, 1-phenyl-7-acetoxymethyl acenaphthylene, 1-phenyl-8-acetoxymethyl Examples include acenaphthylene, 1,2-diphenyl-3-acetoxymethyl acenaphthylene, 1,2-diphenyl-4-acetoxymethyl acenaphthylene, 1,2-diphenyl-5-acetoxymethyl acenaphthylene, and the like.
メトキシメチルアセナフチレン類としては、3−メトキシメチルアセナフチレン、4−メトキシメチルアセナフチレン、5−メトキシメチルアセナフチレン、1−メチル−3−メトキシメチルアセナフチレン、1−メチル−4−メトキシメチルアセナフチレン、1−メチル−5−メトキシメチルアセナフチレン、1−メチル−6−メトキシメチルアセナフチレン、1−メチル−7−メトキシメチルアセナフチレン、1−メチル−8−メトキシメチルアセナフチレン、1,2−ジメチル−3−メトキシメチルアセナフチレン、1,2−ジメチル−4−メトキシメチルアセナフチレン、1,2−ジメチル−5−メトキシメチルアセナフチレン、1−フェニル−3−メトキシメチルアセナフチレン、1−フェニル−4−メトキシメチルアセナフチレン、1−フェニル−5−メトキシメチルアセナフチレン、1−フェニル−6−メトキシメチルアセナフチレン、1−フェニル−7−メトキシメチルアセナフチレン、1−フェニル−8−メトキシメチルアセナフチレン、1,2−ジフェニル−3−メトキシメチルアセナフチレン、1,2−ジフェニル−4−メトキシメチルアセナフチレン、1,2−ジフェニル−5−メトキシメチルアセナフチレンなどが挙げられる。 Examples of methoxymethyl acenaphthylenes include 3-methoxymethyl acenaphthylene, 4-methoxymethyl acenaphthylene, 5-methoxymethyl acenaphthylene, 1-methyl-3-methoxymethyl acenaphthylene, 1-methyl-4. -Methoxymethylacenaphthylene, 1-methyl-5-methoxymethylacenaphthylene, 1-methyl-6-methoxymethylacenaphthylene, 1-methyl-7-methoxymethylacenaphthylene, 1-methyl-8-methoxy Methyl acenaphthylene, 1,2-dimethyl-3-methoxymethyl acenaphthylene, 1,2-dimethyl-4-methoxymethyl acenaphthylene, 1,2-dimethyl-5-methoxymethyl acenaphthylene, 1-phenyl -3-methoxymethyl acenaphthylene, 1-phenyl-4-methoxymethyl acenaphthylene 1-phenyl-5-methoxymethyl acenaphthylene, 1-phenyl-6-methoxymethyl acenaphthylene, 1-phenyl-7-methoxymethyl acenaphthylene, 1-phenyl-8-methoxymethyl acenaphthylene, , 2-diphenyl-3-methoxymethyl acenaphthylene, 1,2-diphenyl-4-methoxymethyl acenaphthylene, 1,2-diphenyl-5-methoxymethyl acenaphthylene, and the like.
上記例示したアセナフチレン類以外にも、3−フェノキシメチルアセナフチレン、4−フェノキシメチルアセナフチレン、5−フェノキシメチルアセナフチレン、3−ビニルオキシメチルアセナフチレン、4−ビニルオキシメチルアセナフチレン、5−ビニルオキシメチルアセナフチレンなどを挙げることができる。 In addition to the acenaphthylenes exemplified above, 3-phenoxymethyl acenaphthylene, 4-phenoxymethyl acenaphthylene, 5-phenoxymethyl acenaphthylene, 3-vinyloxymethyl acenaphthylene, 4-vinyloxymethyl acenaphthylene , 5-vinyloxymethylacenaphthylene and the like.
これらのアセナフチレン類のうち、特に、アセナフチレン、3−ヒドロキシメチルアセナフチレン、4−ヒドロキシメチルアセナフチレン、5−ヒドロキシメチルアセナフチレン、3−アセトキシメチルアセナフチレン、4−アセトキシメチルアセナフチレン、5−アセトキシメチルアセナフチレン、3−メトキシメチルアセナフチレン、4−メトキシメチルアセナフチレン、5−メトキシメチルアセナフチレンなどが好ましい。 Among these acenaphthylenes, in particular, acenaphthylene, 3-hydroxymethyl acenaphthylene, 4-hydroxymethyl acenaphthylene, 5-hydroxymethyl acenaphthylene, 3-acetoxymethyl acenaphthylene, 4-acetoxymethyl acenaphthylene 5-acetoxymethyl acenaphthylene, 3-methoxymethyl acenaphthylene, 4-methoxymethyl acenaphthylene, 5-methoxymethyl acenaphthylene and the like are preferable.
上記アセナフチレン類は、1種単独でまたは2種以上を混合して使用することができる。 The acenaphthylenes can be used singly or in combination of two or more.
<フラーレン化合物(B)>
本発明において、フラーレン化合物は、反射防止膜とこの上に形成されるレジスト膜と
の間でインターミキシングが発生することを防止するために用いられる。また、フラーレン化合物は反射防止膜形成用組成物を塗布した後のクラックの発生を防止する役割も果たす。
<Fullerene compound (B)>
In the present invention, the fullerene compound is used for preventing intermixing between the antireflection film and the resist film formed thereon. The fullerene compound also plays a role in preventing the occurrence of cracks after the application of the composition for forming an antireflection film.
本発明に用いられるフラーレン化合物(B)としては、フラーレンC35、C60、C70、C76、C82、C84、C90、C95、カルボキシル基置換フラーレンC60、カルボキシル基置換フラーレンC70、メトキシカルボニル置換フラーレンC60、メトキシカルボニル置換フラーレンC70、水素化フラーレンC60、水素化フラーレンC70、アルキル置換フラーレンC60、アルキル置換フラーレンC70などが挙げられる。 As the fullerene compound (B) used in the present invention, fullerene C 35 , C 60 , C 70 , C 76 , C 82 , C 84 , C 90 , C 95 , carboxyl group-substituted fullerene C 60 , carboxyl group-substituted fullerene C 70, methoxycarbonyl substituted fullerene C 60, methoxycarbonyl substituted fullerene C 70, hydrogenated fullerene C 60, hydrogenated fullerene C 70, alkyl-substituted fullerene C 60, and the like alkyl-substituted fullerene C 70.
これらフラーレンは、公知の方法によって合成することができる。たとえば、フラーレンC36の製造方法はNew Daiamond.,vol.16,No.2,2000,p.30−31に開示されている。フラーレンC60、C70、C76、C78、C82、C84、C90およびC96の製造方法としては、J.Phy.Chem.,94,8634(1990)にアーク放電法による製造方法が、Z.Phys.D,40,414(1997)にオーブン・レーザー法による製造方法がそれぞれ開示されている。また、1分子中の炭素数が96を超えかつ最大凝集塊径が30nm以下の高次フラーレンは上記アーク放電法の副成物として得ることができる。 These fullerenes can be synthesized by known methods. For example, a method for producing fullerene C 36 is described in New Diamond. , Vol. 16, no. 2, 2000, p. 30-31. As a method for producing fullerenes C 60 , C 70 , C 76 , C 78 , C 82 , C 84 , C 90 and C 96 , J. Phy. Chem. , 94, 8634 (1990), a manufacturing method using an arc discharge method is disclosed in Z. Phys. D, 40, 414 (1997) disclose a production method by an oven laser method. Higher order fullerene having more than 96 carbon atoms in one molecule and a maximum aggregate diameter of 30 nm or less can be obtained as a by-product of the arc discharge method.
フラーレンC60およびC70の市販品としては、フロンティアカーボン(株)製、MATERIALS TECHNOLOGIES RESEARCH MTR LIMITED社製などのフラーレンが挙げられ、フラーレンC76、C78およびC84の市販品としては、MATERIALS TECHNOLOGIES RESEARCH MTR LIMITED社製などのフラーレンが挙げられる。 Commercial products of fullerenes C 60 and C 70 include fullerenes such as those manufactured by Frontier Carbon Co., Ltd. and MATERIALS TECHNOLOGIES RESEARCH MTR LIMITED. Commercial products of fullerenes C 76 , C 78 and C 84 include MATERIALS TECHNOLOGIES. Fullerenes such as those manufactured by RESEARCH MTR LIMITED may be mentioned.
本発明に用いられるフラーレン化合物(B)は、1種類のフラーレンでも炭素数の異なるフラーレンの混合物でも本発明の目的を達成することができる。前記混合物の市販品としては、フロンティアカーボン(株)製またはMATERIALS TECHNOLOGIES RESEARCH MTR LIMITED社製のフラーレンC60/C70の混合物が挙げられる。 The fullerene compound (B) used in the present invention can achieve the object of the present invention even if it is one kind of fullerene or a mixture of fullerenes having different carbon numbers. Examples of commercially available products of the mixture, a mixture of Frontier Carbon Corp. or MATERIALS TECHNOLOGIES RESEARCH MTR LIMITED Co. fullerene C 60 / C 70 and the like.
本発明では、フラーレン化合物(B)としてフラーレン誘導体を用いることもできる。フラーレン誘導体としては、官能基含有フラーレン誘導体やヘテロ環含有フラーレン誘導体が挙げられる。 In the present invention, a fullerene derivative can also be used as the fullerene compound (B). Examples of fullerene derivatives include functional group-containing fullerene derivatives and heterocyclic-containing fullerene derivatives.
官能基含有フラーレン誘導体は、上記フラーレンの表面に炭素数1〜6のアルキル基、炭素数2〜6のアルケニル基、炭素数2〜6のアルキニル基、カルボキシル基、ヒドロキシル基、エポキシ基、アミノ基などの官能基を有するものである。これらのうち、アミノ基は−NR8 2で表され、R8としてはそれぞれ独立に、水素原子、炭素数1〜6のアルキ
ル基、炭素数2〜6のアルケニル基、炭素数2〜6のアルキニル基または分子量30〜50,000のポリエーテル鎖であることが好ましい。上記アミノ基においてR8がポリエ
ーテル鎖である場合、その末端は水酸基または炭素数1〜6のアルコキシル基であることが好ましい。
The functional group-containing fullerene derivative has an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, an alkynyl group having 2 to 6 carbon atoms, a carboxyl group, a hydroxyl group, an epoxy group, and an amino group on the surface of the fullerene. It has a functional group such as Among these, an amino group is represented by —NR 8 2 , and each R 8 is independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an alkyl group having 2 to 6 carbon atoms. An alkynyl group or a polyether chain having a molecular weight of 30 to 50,000 is preferred. In the amino group, when R 8 is a polyether chain, the terminal is preferably a hydroxyl group or an alkoxyl group having 1 to 6 carbon atoms.
官能基含有フラーレン誘導体は、たとえば、Science,252,548(1991)およびJ.Am.Chem.Soc,114,1103(1992)に開示されているエポキシ化反応、Angew.Chem.Int.Ed.Engl.,30,1309(1991)に開示されている1級または2級アミンの付加反応、J.Am.Chem.Soc,114,7301(1992)に開示されているDiels−Alder反応、またはJ.Chem.Soc.,Chem.Commun.,1791(1992)に開
示されているポリ水酸化反応などの公知の方法により合成することができる。
Functional group-containing fullerene derivatives are described, for example, in Science, 252, 548 (1991) and J. Org. Am. Chem. Soc, 114, 1103 (1992), Angew. Chem. Int. Ed. Engl. , 30, 1309 (1991), addition reactions of primary or secondary amines, J. Org. Am. Chem. Soc, 114, 7301 (1992), or the Diels-Alder reaction, Chem. Soc. , Chem. Commun. 1791 (1992), and can be synthesized by a known method such as a polyhydroxylation reaction.
ヘテロ環含有フラーレン誘導体は、フラーレンにヘテロ環を有する基が結合したフラーレン誘導体である。ヘテロ環を有する基としては、ヘテロ環がフラン環および/またはチオフェン環である基が好ましい。 The heterocycle-containing fullerene derivative is a fullerene derivative in which a group having a heterocycle is bonded to fullerene. As the group having a hetero ring, a group in which the hetero ring is a furan ring and / or a thiophene ring is preferable.
ヘテロ環含有フラーレンの誘導体は、フラーレンとフラン環などのヘテロ環を有する化合物とのDiels−Alder反応によって得ることができる。具体的には、フラーレンと、フルフリルアルコール、塩化フロイル、カルボキシルフラン、フルフリルアミンなどのヘテロ環を有する化合物とを、両者が溶解する溶剤中で撹拌することで反応を進行させることができる。この場合、フラーレンとヘテロ環のモル比がフラーレン/ヘテロ環<1を満たす量のフラーレンおよびヘテロ環を有する化合物を用い、30〜100℃の温度条件で反応させることが好ましい。 A derivative of a heterocycle-containing fullerene can be obtained by a Diels-Alder reaction between a fullerene and a compound having a heterocycle such as a furan ring. Specifically, the reaction can be allowed to proceed by stirring the fullerene and a compound having a heterocycle such as furfuryl alcohol, furoyl chloride, carboxyl furan, and furfurylamine in a solvent in which both are dissolved. In this case, it is preferable to perform the reaction under a temperature condition of 30 to 100 ° C. using a compound having a fullerene and a heterocycle in an amount satisfying a fullerene / heterocycle molar ratio of fullerene / heterocycle <1.
ヘテロ環含有フラーレンの誘導体は、1種単独で用いてもよく、その他のフラーレン誘導体と組み合わせて用いてもよい。本発明においては、その他のフラーレン誘導体や分子内に複数のヘテロ環を有する化合物との相溶性、溶剤や液晶配向剤を構成する重合体への溶解・分散性に優れるため、フラーレンの誘導体としてはヘテロ環含有フラーレンの誘導体が好ましい。 Heterocycle-containing fullerene derivatives may be used alone or in combination with other fullerene derivatives. In the present invention, the compatibility with other fullerene derivatives and compounds having a plurality of heterocycles in the molecule, and the solubility and dispersibility in the polymer constituting the solvent and liquid crystal aligning agent are excellent. Heterocycle-containing fullerene derivatives are preferred.
本発明に用いられるフラーレン化合物(B)は、フラーレンC60および/またはフラーレンC70あるいはそれらの誘導体を含有することがより好ましく、フラーレンC60および/またはフラーレンC70を含有することがさらに好ましい。 The fullerene compound (B) used in the present invention preferably contains fullerene C 60 and / or fullerene C 70 or a derivative thereof, and more preferably contains fullerene C 60 and / or fullerene C 70 .
本発明に用いられるフラーレン化合物(B)は、フラーレン化合物(B)全量に対して、フラーレンC60とフラーレンC70の合計が50〜90重量%であるフラーレン混合物を含有することも好ましく、たとえば、フラーレンC60とフラーレンC70の合計が50〜90重量%である粗製フラーレンを用いることができる。このような粗製フラーレンは、高純度な精製フラーレンなどを用いる場合と比較して低コストで本発明に係る反射防止膜形成用組成物を得ることができる。 The fullerene compound (B) used in the present invention preferably contains a fullerene mixture in which the total of fullerene C 60 and fullerene C 70 is 50 to 90% by weight based on the total amount of the fullerene compound (B). Crude fullerene in which the total of fullerene C 60 and fullerene C 70 is 50 to 90% by weight can be used. Such a crude fullerene can obtain the composition for forming an antireflection film according to the present invention at a lower cost than the case of using a high-purity purified fullerene or the like.
<重合体>
本発明に係る反射防止膜形成用組成物に含まれる重合体は、上記化合物(A−1)または(A−2)と上記フラーレン化合物(B)とを混合して、40〜200℃、好ましくは50〜180℃の範囲の温度で加熱することにより製造することができる。
<Polymer>
The polymer contained in the composition for forming an antireflection film according to the present invention is a mixture of the compound (A-1) or (A-2) and the fullerene compound (B), preferably 40 to 200 ° C., preferably Can be produced by heating at a temperature in the range of 50 to 180 ° C.
ビニル基を有する化合物として上記化合物(A−1)を使用する場合、化合物(A−1)とフラーレン化合物(B)との混合モル比((A−1):(B))は、通常1:99〜99:1であり、好ましくは5:95〜95:5、さらに好ましくは10:90〜90:10である。 When the compound (A-1) is used as the compound having a vinyl group, the mixing molar ratio ((A-1) :( B)) of the compound (A-1) and the fullerene compound (B) is usually 1 : 99-99: 1, preferably 5: 95-95: 5, more preferably 10: 90-90: 10.
ビニル基を有する化合物として上記化合物(A−2)を使用する場合、化合物(A−2)とフラーレン化合物(B)との混合モル比((A−2):(B))は、通常1:99〜99:1であり、好ましくは5:95〜95:5、さらに好ましくは10:90〜90:10である。 When the compound (A-2) is used as the compound having a vinyl group, the mixing molar ratio ((A-2) :( B)) of the compound (A-2) and the fullerene compound (B) is usually 1 : 99-99: 1, preferably 5: 95-95: 5, more preferably 10: 90-90: 10.
フラーレン化合物(B)が1mol%未満になるとエッチング耐性が十分な反射防止膜が得られない。またフラーレン化合物(B)が99mol%を超えると溶媒に対する重合体の溶解性が低下する。 When the fullerene compound (B) is less than 1 mol%, an antireflection film having sufficient etching resistance cannot be obtained. When the fullerene compound (B) exceeds 99 mol%, the solubility of the polymer in the solvent decreases.
このような重合体としては、下記式(1)で表される繰り返し単位(a−1)とフラーレン構造を有する繰り返し単位(b)とを有する重合体(以下、「重合体(I)」という)や、下記式(2)で表される繰り返し単位(a−2)とフラーレン構造を有する繰り返し単位(b)とを有する重合体(以下、「重合体(II)」という)が挙げられる。 As such a polymer, a polymer having a repeating unit (a-1) represented by the following formula (1) and a repeating unit (b) having a fullerene structure (hereinafter referred to as “polymer (I)”). And a polymer having a repeating unit (a-2) represented by the following formula (2) and a repeating unit (b) having a fullerene structure (hereinafter referred to as “polymer (II)”).
式(1)において、R1は水素原子またはフッ素原子を示し、R2およびR3はそれぞれ
独立に水素原子、フッ素原子または1価の基を示し、R4はハロゲン原子または1価の基
を示す。
In the formula (1), R 1 represents a hydrogen atom or a fluorine atom, R 2 and R 3 each independently represent a hydrogen atom, a fluorine atom or a monovalent group, and R 4 represents a halogen atom or a monovalent group. Show.
式(2)において、R5、R6およびR7はそれぞれ独立に水素原子、ハロゲン原子また
は1価の基を示す。
In the formula (2), R 5 , R 6 and R 7 each independently represent a hydrogen atom, a halogen atom or a monovalent group.
前記重合体は、繰り返し単位(a−1)または(a−2)と繰り返し単位(b)とを有する共重合体を形成してもよく、繰り返し単位(a−1)または(a−2)からなる重合体と繰り返し単位(b)からなる重合体との混合物であってもよい。 The polymer may form a copolymer having the repeating unit (a-1) or (a-2) and the repeating unit (b), and the repeating unit (a-1) or (a-2) It is also possible to use a mixture of a polymer consisting of the above and a polymer consisting of the repeating unit (b).
さらに、前記重合体として、繰り返し単位(a−1)を有する重合体にフラーレン化合物(B)が混入した重合体(以下、「重合体(III)」という)や、繰り返し単位(a−
2)を有する重合体にフラーレン化合物(B)が混入した重合体(以下、「重合体(IV)」という)が挙げられる。
Further, as the polymer, a polymer having a repeating unit (a-1) mixed with a fullerene compound (B) (hereinafter referred to as “polymer (III)”), a repeating unit (a-
2) and a polymer in which the fullerene compound (B) is mixed (hereinafter referred to as “polymer (IV)”).
このような重合体のうち、化合物(A−1)または(A−2)とフラーレン化合物(B)との共重合体が好ましい。 Among such polymers, a copolymer of the compound (A-1) or (A-2) and the fullerene compound (B) is preferable.
化合物(A−1)または(A−2)とフラーレン化合物(B)とから得られる重合体の
ゲルパーミエーションクロマトグラフィにより測定した重量平均分子量(以下「Mw」という)は、ポリスチレン換算で3000〜100,000、好ましくは3,000〜20,000である。
The weight average molecular weight (hereinafter referred to as “Mw”) measured by gel permeation chromatography of the polymer obtained from the compound (A-1) or (A-2) and the fullerene compound (B) is 3000 to 100 in terms of polystyrene. 1,000, preferably 3,000 to 20,000.
重合方法としては溶液重合が好ましく、このとき用いる溶媒としては、ベンゼン、トルエン、エチルベンゼン、アニソール、クロロベンゼン、ジクロロベンゼン、トリクロロベンゼンなどの芳香族系溶媒が好ましい。重合開始剤は特に制限はないが、アゾ系開始剤、過酸化物系開始剤などが用いられる。 The polymerization method is preferably solution polymerization, and the solvent used at this time is preferably an aromatic solvent such as benzene, toluene, ethylbenzene, anisole, chlorobenzene, dichlorobenzene, or trichlorobenzene. The polymerization initiator is not particularly limited, but an azo initiator, a peroxide initiator, or the like is used.
本発明では、前記重合体(I)〜(IV)のうちの1つを単独で使用してもよいが、これらの重合体の2種以上のブレンド物を使用することもできる。 In the present invention, one of the polymers (I) to (IV) may be used alone, but a blend of two or more of these polymers can also be used.
<架橋剤(C)>
本発明に係る反射防止膜形成用組成物は、上記重合体(I)〜(IV)から選択される少なくとも1種の重合体に加えて、架橋剤(C)として多核フェノール類、アジド化合物、または市販の硬化剤を使用することができる。
<Crosslinking agent (C)>
In addition to at least one polymer selected from the above polymers (I) to (IV), the composition for forming an antireflection film according to the present invention includes polynuclear phenols, azide compounds as a crosslinking agent (C), Or a commercially available hardening | curing agent can be used.
多核フェノール類としては、たとえば、4,4’−ビフェニルジオール、4,4’−メチレンビスフェノール、4,4’−エチリデンビスフェノール、ビスフェノールAなどの2核フェノール類;4,4’,4”−メチリデントリスフェノール、4,4’−〔1−{4−(1−[4−ヒドロキシフェニル]−1−メチルエチル)フェニル}エチリデン〕ビスフェノールなどの3核フェノール類;ノボラックなどのポリフェノール類などを挙げることができる。 Examples of polynuclear phenols include dinuclear phenols such as 4,4′-biphenyldiol, 4,4′-methylene bisphenol, 4,4′-ethylidene bisphenol, and bisphenol A; 4,4 ′, 4 ″ -methyl. Trinuclear phenols such as reddentrisphenol, 4,4 ′-[1- {4- (1- [4-hydroxyphenyl] -1-methylethyl) phenyl} ethylidene] bisphenol; polyphenols such as novolak be able to.
これらの多核フェノール類のうち、4,4’−〔1−{4−(1−[4−ヒドロキシフェニル]−1−メチルエチル)フェニル}エチリデン〕ビスフェノール、ノボラックなどが好ましい。 Of these polynuclear phenols, 4,4 '-[1- {4- (1- [4-hydroxyphenyl] -1-methylethyl) phenyl} ethylidene] bisphenol, novolac and the like are preferable.
アジド化合物としては、DZDS、BAP−P、DR−94Cl、DAzST(51)、DAzST(4)、DAzST(86)、ジアジドカルコン、DAzST−Na、DAzBA(Na)、BAC−H、BAC−M、BAC−E(以上、商品名、東洋合成工業(株)製)などを用いることができる。 As azide compounds, DZDS, BAP-P, DR-94Cl, DAzST (51), DAzST (4), DAzST (86), diazide chalcone, DAzST-Na, DAzBA (Na), BAC-H, BAC-M BAC-E (trade name, manufactured by Toyo Gosei Co., Ltd.) and the like can be used.
硬化剤としては、たとえば、2,3−トリレンジイソシアナート、2,4−トリレンジイソシアナート、3,4−トリレンジイソシアナート、3,5−トリレンジイソシアナート、4,4’−ジフェニルメタンジイソシアナート、ヘキサメチレンジイソシアナート、1,4−シクロヘキサンジイソシアナートなどのジイソシアナート類;エピコート812、同815、同826、同828、同834、同836、同871、同1001、同1004、同1007、同1009、同1031(以上、商品名、油化シェルエポキシ(株)製)、アラルダイト6600、同6700、同6800、同502、同6071、同6084、同6097、同6099(以上、商品名、チバガイギー社製)、DER331、同332、同333、同661、同644、同667(以上、商品名、ダウケミカル社製)などのエポキシ化合物;サイメル300、同301、同303、同350、同370、同771、同325、同327、同703、同712、同701、同272、同202、マイコート506、同508(以上、商品名、三井サイアナミッド(株)製)などのメラミン系硬化剤;サイメル1123、同1123−10、同1128、マイコート102、同105、同106、同130(以上、商品名、三井サイアナミッド(株)製)などのベンゾグアナミン系硬化剤;サイメル1170、同1172(以上、商品名、三井サイアナミッド(株)製)、ニカラックN―2702(商品名、三和ケミカル(株)製)などのグリコールウリル系硬化剤などを挙げることができる。 Examples of the curing agent include 2,3-tolylene diisocyanate, 2,4-tolylene diisocyanate, 3,4-tolylene diisocyanate, 3,5-tolylene diisocyanate, and 4,4′-diphenylmethane diester. Diisocyanates such as isocyanate, hexamethylene diisocyanate, 1,4-cyclohexane diisocyanate; Epicoat 812, 815, 826, 828, 834, 836, 871, 1001, 1004 , 1007, 1009, 1031 (trade name, manufactured by Yuka Shell Epoxy Co., Ltd.), Araldite 6600, 6700, 6800, 502, 6071, 6084, 6097, 6099 (above) , Product name, manufactured by Ciba Geigy), DER331, 332, 333, 661, 644, 667 (trade name, manufactured by Dow Chemical Co., Ltd.) and the like; Cymel 300, 301, 303, 350, 370, 771, 325, 327, 703, 712, Melamine-based curing agents such as 701, 272, 202, My Coat 506, 508 (above, trade name, manufactured by Mitsui Cyanamid Co., Ltd.); Cymel 1123, 1123-10, 1128, My Coat 102, Benzoguanamine-based curing agents such as 105, 106 and 130 (trade names, manufactured by Mitsui Cyanamid Co., Ltd.); Cymel 1170, 1172 (trade names, manufactured by Mitsui Cyanamid Co., Ltd.), Nicarak N- And glycoluril-based curing agents such as 2702 (trade name, manufactured by Sanwa Chemical Co., Ltd.).
これらの架橋剤(C)は1種単独でまたは2種以上を混合して使用することができる。架橋剤(C)の配合量は、反射防止膜形成用組成物の固形分100重量部当たり、通常20重量部以下、好ましくは10重量部以下である。 These crosslinking agents (C) can be used individually by 1 type or in mixture of 2 or more types. The amount of the crosslinking agent (C) is usually 20 parts by weight or less, preferably 10 parts by weight or less per 100 parts by weight of the solid content of the composition for forming an antireflection film.
<酸発生剤(D)>
本発明に係る反射防止膜形成用組成物は、露光あるいは加熱により酸を発生する酸発生剤(D)をさらに含有してもよい。
<Acid generator (D)>
The composition for forming an antireflection film according to the present invention may further contain an acid generator (D) that generates an acid by exposure or heating.
(光酸発生剤)
露光により酸を発生する酸発生剤(以下、「光酸発生剤」という)としては、たとえば、オニウム塩系光酸発生剤類、ハロゲン含有化合物系光酸発生剤類、ジアゾケトン化合物系光酸発生剤類、スルホン化合物系光酸発生剤類、スルホン酸化合物系光酸発生剤類が挙げられる。
(Photoacid generator)
Examples of acid generators that generate acid upon exposure (hereinafter referred to as “photoacid generators”) include onium salt photoacid generators, halogen-containing compound photoacid generators, and diazoketone compound photoacid generators. Agents, sulfone compound photoacid generators, and sulfonic acid compound photoacid generators.
オニウム塩系光酸発生剤類としては、ジフェニルヨードニウムトリフルオロメタンスルホネート、ジフェニルヨードニウムノナフルオロ−n−ブタンスルホネート、ジフェニルヨードニウムピレンスルホネート、ジフェニルヨードニウム−n−ドデシルベンゼンスルホネート、ジフェニルヨードニウム10−カンファースルホネート、ジフェニルヨードニウムナフタレンスルホネート、ジフェニルヨードニウムヘキサフルオロアンチモネート、ビス(4−t−ブチルフェニル)ヨードニウムトリフルオロメタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウムノナフルオロ−n−ブタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウムn−ドデシルベンゼンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウム10−カンファースルホネート、ビス(4−t−ブチルフェニル)ヨードニウムナフタレンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウムヘキサフルオロアンチモネート、トリフェニルスルホニウムトリフルオロメタンスルホネート、トリフェニルスルホニウムノナフルオロ−n−ブタンスルホネート、トリフェニルスルホニウム−n−ドデシルベンゼンスルホネート、トリフェニルスルホニウムナフタレンスルホネート、トリフェニルスルホニウム10−カンファースルホネート、トリフェニルスルホニウムヘキサフルオロアンチモネート、4−ヒドロキシフェニル・フェニル・メチルスルホニウム−p−トルエンスルホネート、4−ヒドロキシフェニル・ベンジル・メチルスルホニウム−p−トルエンスルホネート、
シクロヘキシル・メチル・2−オキソシクロヘキシルスルホニウムトリフルオロメタンスルホネート、2−オキソシクロヘキシルジシクロヘキシルスルホニウムトリフルオロメタンスルホネート、2−オキソシクロヘキシルジメチルスルホニウムトリフルオロメタンスルホネート、1−ナフチルジメチルスルホニウムトリフルオロメタンスルホネート、1−ナフチルジエチルスルホニウムトリフルオロメタンスルホネート、4−シアノ−1−ナフチルジメチルスルホニウムトリフルオロメタンスルホネート、4−シアノ−1−ナフチルジエチルスルホニウムトリフルオロメタンスルホネート、4−ニトロ−1−ナフチルジメチルスルホニウムトリフルオロメタンスルホネート、4−ニトロ−1−ナフチルジエチルスルホニウムトリフルオロメタンスルホネート、4−メチル−1−ナフチルジメチルスルホニウムトリフルオロメタンスルホネート、4−メチル−1−ナフチルジエチルスルホニウムトリフルオロメタンスルホネート、4−ヒドロキシ−1−ナフチルジメチルスルホニウムトリフルオロメタンスルホネート、4−ヒドロキシ−1−ナフチルジエチルスルホニウムトリフルオロメタンスルホネート、
1−(4−ヒドロキシナフタレン−1−イル)テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−(4−メトキシナフタレン−1−イル)テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−(4−エトキシナフタレン−1−イル)テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−(4−メトキシメトキシナフタレン−1−イル)テトラヒドロチオフェニウムトリフルオロメタンスルホネート
、1−(4−エトキシメトキシナフタレン−1−イル)テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−〔4−(1−メトキシエトキシ)ナフタレン−1−イル〕テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−〔4−(2−メトキシエトキシ)ナフタレン−1−イル〕テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−(4−メトキシカルボニルオキシナフタレン−1−イル)テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−(4−エトキシカルボニルオキシナフタレン−1−イル)テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−(4−n−プロポキシカルボニルオキシナフタレン−1−イル)テトラヒドロチオフェニウムトリフルオロメタンスルホネート、
1−(4−i−プロポキシカルボニルオキシナフタレン−1−イル)テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−(4−n−ブトキカルボニルオキシナフタレン−1−イル)テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−(4−t−ブトキシカルボニルオキシナフタレン−1−イル)テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−〔4−(2−テトラヒドロフラニルオキシ)ナフタレン−1−イル〕テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−〔4−(2−テトラヒドロピラニルオキシ)ナフタレン−1−イル〕テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−(4−ベンジルオキシ)テトラヒドロチオフェニウムトリフルオロメタンスルホネート、1−(ナフチルアセトメチル)テトラヒドロチオフェニウムトリフルオロメタンスルホネートなどが挙げられる。
Examples of onium salt photoacid generators include diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoro-n-butanesulfonate, diphenyliodoniumpyrenesulfonate, diphenyliodonium-n-dodecylbenzenesulfonate, diphenyliodonium 10-camphorsulfonate, diphenyliodonium. Naphthalenesulfonate, diphenyliodonium hexafluoroantimonate, bis (4-tert-butylphenyl) iodonium trifluoromethanesulfonate, bis (4-tert-butylphenyl) iodonium nonafluoro-n-butanesulfonate, bis (4-tert-butylphenyl) ) Iodonium n-dodecylbenzenesulfonate, bis (4-t-butylphenyl) iodoni 10-camphorsulfonate, bis (4-t-butylphenyl) iodonium naphthalenesulfonate, bis (4-t-butylphenyl) iodonium hexafluoroantimonate, triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium nonafluoro-n-butane Sulfonate, triphenylsulfonium-n-dodecylbenzenesulfonate, triphenylsulfonium naphthalenesulfonate, triphenylsulfonium 10-camphorsulfonate, triphenylsulfonium hexafluoroantimonate, 4-hydroxyphenyl phenylmethylsulfonium-p-toluenesulfonate, 4 -Hydroxyphenyl benzyl methylsulfonium-p-toluenesulfonate,
Cyclohexylmethyl 2-oxocyclohexylsulfonium trifluoromethanesulfonate, 2-oxocyclohexyldicyclohexylsulfonium trifluoromethanesulfonate, 2-oxocyclohexyldimethylsulfonium trifluoromethanesulfonate, 1-naphthyldimethylsulfonium trifluoromethanesulfonate, 1-naphthyldiethylsulfonium trifluoromethanesulfonate 4-cyano-1-naphthyldimethylsulfonium trifluoromethanesulfonate, 4-cyano-1-naphthyldiethylsulfonium trifluoromethanesulfonate, 4-nitro-1-naphthyldimethylsulfonium trifluoromethanesulfonate, 4-nitro-1-naphthyldiethylsulfonium trifluoro Lome Sulfonate, 4-methyl-1-naphthyldimethylsulfonium trifluoromethanesulfonate, 4-methyl-1-naphthyldiethylsulfonium trifluoromethanesulfonate, 4-hydroxy-1-naphthyldimethylsulfonium trifluoromethanesulfonate, 4-hydroxy-1-naphthyldiethyl Sulfonium trifluoromethanesulfonate,
1- (4-hydroxynaphthalen-1-yl) tetrahydrothiophenium trifluoromethanesulfonate, 1- (4-methoxynaphthalen-1-yl) tetrahydrothiophenium trifluoromethanesulfonate, 1- (4-ethoxynaphthalene-1- Yl) tetrahydrothiophenium trifluoromethanesulfonate, 1- (4-methoxymethoxynaphthalen-1-yl) tetrahydrothiophenium trifluoromethanesulfonate, 1- (4-ethoxymethoxynaphthalen-1-yl) tetrahydrothiophenium trifluoromethane Sulfonate, 1- [4- (1-methoxyethoxy) naphthalen-1-yl] tetrahydrothiophenium trifluoromethanesulfonate, 1- [4- (2-methoxyethoxy) naphthalene 1-yl] tetrahydrothiophenium trifluoromethanesulfonate, 1- (4-methoxycarbonyloxynaphthalen-1-yl) tetrahydrothiophenium trifluoromethanesulfonate, 1- (4-ethoxycarbonyloxynaphthalen-1-yl) tetrahydrothio Phenium trifluoromethanesulfonate, 1- (4-n-propoxycarbonyloxynaphthalen-1-yl) tetrahydrothiophenium trifluoromethanesulfonate,
1- (4-i-propoxycarbonyloxynaphthalen-1-yl) tetrahydrothiophenium trifluoromethanesulfonate, 1- (4-n-butoxycarbonyloxynaphthalen-1-yl) tetrahydrothiophenium trifluoromethanesulfonate, 1 -(4-t-butoxycarbonyloxynaphthalen-1-yl) tetrahydrothiophenium trifluoromethanesulfonate, 1- [4- (2-tetrahydrofuranyloxy) naphthalen-1-yl] tetrahydrothiophenium trifluoromethanesulfonate, 1 -[4- (2-tetrahydropyranyloxy) naphthalen-1-yl] tetrahydrothiophenium trifluoromethanesulfonate, 1- (4-benzyloxy) tetrahydrothiophenium trifluoro Tan sulfonate, 1- (such as naphthyl acetamide methyl) tetrahydrothiophenium trifluoromethanesulfonate, and the like.
ハロゲン含有化合物系光酸発生剤類としては、フェニルビス(トリクロロメチル)−s−トリアジン、4−メトキシフェニルビス(トリクロロメチル)−s−トリアジン、1−ナフチルビス(トリクロロメチル)−s−トリアジンなどが挙げられる。 Examples of halogen-containing compound-based photoacid generators include phenylbis (trichloromethyl) -s-triazine, 4-methoxyphenylbis (trichloromethyl) -s-triazine, 1-naphthylbis (trichloromethyl) -s-triazine, and the like. Can be mentioned.
ジアゾケトン化合物系光酸発生剤類としては、1,2−ナフトキノンジアジド−4−スルホニルクロリド、1,2−ナフトキノンジアジド−5−スルホニルクロリド、2,3,4,4’−テトラヒドロキシベンゾフェノンの1,2−ナフトキノンジアジド−4−スルホン酸エステルまたは1,2−ナフトキノンジアジド−5−スルホン酸エステルなどが挙げられる。 Examples of the diazoketone compound photoacid generators include 1,2-naphthoquinonediazide-4-sulfonyl chloride, 1,2-naphthoquinonediazide-5-sulfonyl chloride, 1,3,4 of 4,4'-tetrahydroxybenzophenone, Examples thereof include 2-naphthoquinonediazide-4-sulfonic acid ester and 1,2-naphthoquinonediazide-5-sulfonic acid ester.
スルホン化合物系光酸発生剤類としては、4−トリスフェナシルスルホン、メシチルフェナシルスルホン、ビス(フェニルスルホニル)メタンなどが挙げられる。 Examples of the sulfone compound photoacid generators include 4-trisphenacylsulfone, mesitylphenacylsulfone, bis (phenylsulfonyl) methane, and the like.
スルホン酸化合物系光酸発生剤類としては、ベンゾイントシレート、ピロガロールのトリス(トリフルオロメタンスルホネート)、ニトロベンジル−9,10−ジエトキシアントラセン−2−スルホネート、トリフルオロメタンスルホニルビシクロ[2,2,1]ヘプト−5−エン−2,3−ジカルボジイミド、N−ヒドロキシスクシンイミドトリフルオロメタンスルホネート、1,8−ナフタレンジカルボン酸イミドトリフルオロメタンスルホネートなどが挙げられる。 Examples of sulfonic acid compound photoacid generators include benzoin tosylate, pyrogallol tris (trifluoromethanesulfonate), nitrobenzyl-9,10-diethoxyanthracene-2-sulfonate, trifluoromethanesulfonylbicyclo [2,2,1]. ] Hept-5-ene-2,3-dicarbodiimide, N-hydroxysuccinimide trifluoromethanesulfonate, 1,8-naphthalenedicarboxylic acid imide trifluoromethanesulfonate, and the like.
これらの光酸発生剤のうち、ジフェニルヨードニウムトリフルオロメタンスルホネート、ジフェニルヨードニウムノナフルオロ−n−ブタンスルホネート、ジフェニルヨードニウムピレンスルホネート、ジフェニルヨードニウムn−ドデシルベンゼンスルホネート、ジフェニルヨードニウム10−カンファースルホネート、ジフェニルヨードニウムナフタレンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウムトリフルオロメタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウムノナフルオロ−n−ブタンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウム−n−ドデシルベンゼンスルホネート、ビス(4−t−ブチルフェニル)ヨードニウム10−カンファースルホネート、ビス(4−t−ブチルフェニル)ヨードニウムナフタレンスルホネートなどが好ましい。 Among these photoacid generators, diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoro-n-butanesulfonate, diphenyliodonium pyrenesulfonate, diphenyliodonium n-dodecylbenzenesulfonate, diphenyliodonium 10-camphorsulfonate, diphenyliodonium naphthalenesulfonate, Bis (4-t-butylphenyl) iodonium trifluoromethanesulfonate, bis (4-t-butylphenyl) iodonium nonafluoro-n-butanesulfonate, bis (4-t-butylphenyl) iodonium-n-dodecylbenzenesulfonate, bis (4-t-butylphenyl) iodonium 10-camphorsulfonate, bis (4-t-butylpheny ) Such as iodonium naphthalene sulfonate is preferred.
上記光酸発生剤は、1種単独でまたは2種以上を混合して使用することができる。上記光酸発生剤を用いる場合、露光量は、通常1〜200mJ/cm2、好ましくは10〜1
00mJ/cm2である。
The said photo-acid generator can be used individually by 1 type or in mixture of 2 or more types. When the photoacid generator is used, the exposure amount is usually 1 to 200 mJ / cm 2 , preferably 10 to 1.
00 mJ / cm 2 .
(熱酸発生剤)
加熱により酸を発生する酸発生剤(以下「熱酸発生剤」という)としては、たとえば、2,4,4,6−テトラブロモシクロヘキサジエノン、ベンゾイントシレート、2−ニトロベンジルトシレート、アルキルスルホネート類などを挙げることができる。
(Thermal acid generator)
Examples of the acid generator that generates an acid upon heating (hereinafter referred to as “thermal acid generator”) include 2,4,4,6-tetrabromocyclohexadienone, benzoin tosylate, 2-nitrobenzyl tosylate, and alkyl. Examples thereof include sulfonates.
これらの熱酸発生剤は、1種単独でまたは2種以上を混合して使用することができる。 These thermal acid generators can be used singly or in combination of two or more.
熱酸発生剤は、焼成時に酸を発生して架橋反応を促進することから、光酸発生剤よりも好ましく用いられる。熱酸発生剤を使用する場合、加熱条件は使用する熱酸発生剤の種類によって適宜決定されるが、加熱温度は、通常150〜400℃、好ましくは200〜350℃であり、加熱時間は、通常1〜10分、好ましくは1〜3分である。 The thermal acid generator is more preferably used than the photoacid generator because it generates an acid during firing to promote a crosslinking reaction. When using a thermal acid generator, the heating conditions are appropriately determined depending on the type of thermal acid generator used, but the heating temperature is usually 150 to 400 ° C., preferably 200 to 350 ° C., and the heating time is Usually 1 to 10 minutes, preferably 1 to 3 minutes.
また、本発明では、酸発生剤(D)として光酸発生剤と熱酸発生剤とを併用することもできる。 Moreover, in this invention, a photo-acid generator and a thermal acid generator can also be used together as an acid generator (D).
酸発生剤(D)の配合量は、反射防止膜形成用組成物の固形分100重量部当たり、通常5,000重量部以下、好ましくは0.1〜1,000重量部、さらに好ましくは0.1〜100重量部である。 The amount of the acid generator (D) is usually 5,000 parts by weight or less, preferably 0.1 to 1,000 parts by weight, more preferably 0, per 100 parts by weight of the solid content of the composition for forming an antireflection film. .1 to 100 parts by weight.
本発明に係る反射防止膜形成用組成物は、上記酸発生剤(D)を含有することにより、常温を含む比較的低温で重合体の分子鎖間に有効に架橋構造を形成することができる。 By containing the acid generator (D), the antireflection film-forming composition according to the present invention can effectively form a crosslinked structure between the molecular chains of the polymer at a relatively low temperature including normal temperature. .
<溶剤(E)>
本発明に係る反射防止膜形成用組成物は、溶剤(E)を含むことが好ましい。このとき使用する溶媒(E)としては、上記重合体および後述するその他の成分を溶解しうるものであれば特に限定されるものではない。
<Solvent (E)>
The composition for forming an antireflection film according to the present invention preferably contains a solvent (E). The solvent (E) used at this time is not particularly limited as long as it can dissolve the polymer and other components described later.
たとえば、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノ−n−プロピルエーテル、エチレングリコールモノ−n−ブチルエーテルなどのエチレングリコールモノアルキルエーテル類;
エチレングリコールモノメチルエーテルアセテート、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノ−n−プロピルエーテルアセテート、エチレングリコールモノ−n−ブチルエーテルアセテートなどのエチレングリコールモノアルキルエーテルアセテート類;
ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールジ−n−プロピルエーテル、ジエチレングリコールジ−n−ブチルエーテルなどのジエチレングリコールジアルキルエーテル類;
トリエチレングリコールジメチルエーテル、トリエチレングリコールジエチルエーテルなどのトリエチレングリコールジアルキルエーテル類;
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エチルエーテル、プロピレングリコールモノ−n−プロピルエーテル、プロピレングリコールモノ−n−ブチルエーテルなどのプロピレングリコールモノアルキルエーテル類;
プロピレングリコールジメチルエーテル、プロピレングリコールジエチルエーテル、プロピレングリコールジ−n−プロピルエーテル、プロピレングリコールジ−n−ブチルエーテルなどのプロピレングリコールジアルキルエーテル類;
プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエテルエーテルアセテート、プロピレングリコールモノ−n−プロピルエーテルアセテート、プロピレングリコールモノ−n−ブチルエーテルアセテートなどのプロピレングリコールモノアルキルエーテルアセテート類;
乳酸メチル、乳酸エチル、乳酸n−プロピル、乳酸i−プロピル、乳酸n−ブチル、乳酸i−ブチルなどの乳酸エステル類;
ギ酸メチル、ギ酸エチル、ギ酸n−プロピル、ギ酸i−プロピル、ギ酸n−ブチル、ギ酸i−ブチル、ギ酸n−アミル、ギ酸i−アミル、酢酸メチル、酢酸エチル、酢酸n−プロピル、酢酸i−プロピル、酢酸n−ブチル、酢酸i−ブチル、酢酸n−アミル、酢酸i−アミル、酢酸n−ヘキシル、プロピオン酸メチル、プロピオン酸エチル、プロピオン酸n−プロピル、プロピオン酸i−プロピル、プロピオン酸n−ブチル、プロピオン酸i−ブチル、酪酸メチル、酪酸エチル、酪酸n−プロピル、酪酸i−プロピル、酪酸n−ブチル、酪酸i−ブチルなどの脂肪族カルボン酸エステル類;
ヒドロキシ酢酸エチル、2−ヒドロキシ−2−メチルプロピオン酸エチル、3−メトキシ−2−メチルプロピオン酸メチル、2−ヒドロキシ−3−メチル酪酸メチル、メトキシ酢酸エチル、エトキシ酢酸エチル、3−メトキシプロピオン酸メチル、3−エトキシプロピオン酸エチル、3−メトキシプロピオン酸エチル、3−メトキシプロピルアセテート、3−メトキシブチルアセテート、3−メチル−3−メトキシブチルアセテート、3−メチル−3−メトキシブチルプロピオネート、3−メチル−3−メトキシブチルブチレート、アセト酢酸メチル、ピルビン酸メチル、ピルビン酸エチルなどの他のエステル類;
トルエン、キシレンなどの芳香族炭化水素類;
メチルエチルケトン、メチル−n−プロピルケトン、メチル−n−ブチルケトン、2−ヘプタノン、3−ヘプタノン、4−ヘプタノン、シクロヘキサノンなどのケトン類;
N−メチルホルムアミド、N,N−ジメチルホルムアミド、N−メチルアセトアミド、N,N−ジメチルアセトアミド、N−メチルピロリドンなどのアミド類;
γ−ブチロラクトンなどのラクトン類などから適宜選択して使用する。
For example, ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether;
Ethylene glycol monoalkyl ether acetates such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol mono-n-propyl ether acetate, ethylene glycol mono-n-butyl ether acetate;
Diethylene glycol dialkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol di-n-propyl ether, diethylene glycol di-n-butyl ether;
Triethylene glycol dialkyl ethers such as triethylene glycol dimethyl ether and triethylene glycol diethyl ether;
Propylene glycol monoalkyl ethers such as propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether;
Propylene glycol dialkyl ethers such as propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene glycol di-n-propyl ether, propylene glycol di-n-butyl ether;
Propylene glycol monoalkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoether ether acetate, propylene glycol mono-n-propyl ether acetate, propylene glycol mono-n-butyl ether acetate;
Lactic acid esters such as methyl lactate, ethyl lactate, n-propyl lactate, i-propyl lactate, n-butyl lactate, i-butyl lactate;
Methyl formate, ethyl formate, n-propyl formate, i-propyl formate, n-butyl formate, i-butyl formate, n-amyl formate, i-amyl formate, methyl acetate, ethyl acetate, n-propyl acetate, i-acetate Propyl, n-butyl acetate, i-butyl acetate, n-amyl acetate, i-amyl acetate, n-hexyl acetate, methyl propionate, ethyl propionate, n-propyl propionate, i-propyl propionate, n propionate Aliphatic carboxylic esters such as butyl, i-butyl propionate, methyl butyrate, ethyl butyrate, n-propyl butyrate, i-propyl butyrate, n-butyl butyrate, i-butyl butyrate;
Ethyl hydroxyacetate, ethyl 2-hydroxy-2-methylpropionate, methyl 3-methoxy-2-methylpropionate, methyl 2-hydroxy-3-methylbutyrate, ethyl methoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate , Ethyl 3-ethoxypropionate, ethyl 3-methoxypropionate, 3-methoxypropyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutylpropionate, 3 -Other esters such as methyl-3-methoxybutyl butyrate, methyl acetoacetate, methyl pyruvate, ethyl pyruvate;
Aromatic hydrocarbons such as toluene and xylene;
Ketones such as methyl ethyl ketone, methyl-n-propyl ketone, methyl-n-butyl ketone, 2-heptanone, 3-heptanone, 4-heptanone, cyclohexanone;
Amides such as N-methylformamide, N, N-dimethylformamide, N-methylacetamide, N, N-dimethylacetamide, N-methylpyrrolidone;
A lactone such as γ-butyrolactone is appropriately selected and used.
これらの溶剤のうち、好ましくは、エチレングリコールモノエチルエーテルアセテート、乳酸エチル、酢酸n−ブチル、3−エトキシプロピオン酸エチル、3−メトキシプロピオン酸メチル、2−ヘプタノン、シクロヘキサノンなどが用いられる。上記溶剤は、1種単独でまたは2種以上を混合して使用することができる。 Of these solvents, ethylene glycol monoethyl ether acetate, ethyl lactate, n-butyl acetate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone and the like are preferably used. The said solvent can be used individually by 1 type or in mixture of 2 or more types.
溶剤(E)は、反射防止膜形成用組成物の固形分濃度が、通常0.01〜70重量%、好ましくは0.05〜60重量%、さらに好ましくは0.1〜50重量%となる範囲の量で使用される。 In the solvent (E), the solid content concentration of the composition for forming an antireflection film is usually 0.01 to 70% by weight, preferably 0.05 to 60% by weight, more preferably 0.1 to 50% by weight. Used in range quantities.
<その他の成分>
本発明に係る反射防止膜形成用組成物には、本発明の効果を損なわない範囲内で、必要に応じて、(F)バインダー樹脂、(G)放射線吸収剤、(H)界面活性剤などの各種の添加剤を配合することができる。また、保存安定剤、消泡剤、接着助剤などの添加剤を配合することもできる。
<Other ingredients>
In the composition for forming an antireflection film according to the present invention, (F) a binder resin, (G) a radiation absorber, (H) a surfactant, etc., as necessary, within a range not impairing the effects of the present invention. These various additives can be blended. In addition, additives such as a storage stabilizer, an antifoaming agent and an adhesion aid can be blended.
(F)バインダー樹脂
バインダー樹脂(F)としては、上記重合体以外の種々の熱可塑性および熱硬化性の合成樹脂を使用することができる。
(F) Binder resin As binder resin (F), various thermoplastic and thermosetting synthetic resins other than the said polymer can be used.
熱可塑性樹脂の例としては、ポリエチレン、ポリプロピレン、ポリ−1−ブテン、ポリ−1−ペンテン、ポリ−1−ヘキセン、ポリ−1−ヘプテン、ポリ−1−オクテン、ポリ−1−デセン、ポリ−1−ドデセン、ポリ−1−テトラデセン、ポリ−1−ヘキサデセン、ポリ−1−オクタデセン、ポリビニルシクロアルカンなどのα−オレフィン重合体;
ポリ−1,4−ペンタジエン、ポリ−1,4−ヘキサジエン、ポリ−1,5−ヘキサジエン、ポリ−1,7−o−クロルアクロレインなどのα,β−不飽和アルデヒド重合体類;ポリメチルビニルケトン、ポリ芳香族ビニルケトン、ポリ環状ビニルケトンなどのα,β−不飽和ケトン重合体類;
ポリ(メタ)アクリル酸、ポリ(メタ)アクリル酸の塩類、ポリ(メタ)アクリル酸のエステル、ポリ(メタ)アクリル酸のハロゲン化物などのα,β−不飽和酸誘導体の重合体類;
ポリ(メタ)アクリル酸無水物、ポリ無水マレイン酸などのα,β−不飽和酸無水物の重合体類;
ポリメチレンマロン酸ジエステル、ポリイタコン酸ジエステルなどの不飽和多塩基酸エステル重合体類;
ポリソルビン酸エステル、ムコン酸エステルなどのジオレフィン酸エステル重合体類;
ポリアクリル酸チオエステル、メタクリル酸チオエステル、α−クロルアクリル酸チオエステルなどのα,β−不飽和酸チオエステル重合体類;
ポリアクリロニトリル、ポリメタクリロニトリルなどのアクリロニトリル誘導体の重合体類;
ポリアクリルアミド、ポリメタクリルアミドなどのアクリルアミド誘導体の重合体類;
スチリル金属化合物重合体類;ポリビニルオキシ金属化合物類;ポリイミン類;
ポリフェニレンオキシド、ポリ−1,3−ジオキソラン、ポリオキシラン、ポリテトラヒドロフラン、ポリテトラヒドロピランなどのポリエーテル類;
ポリスルフィド類;ポリスルホンアミド類;ポリペプチド類;
ナイロン66、ナイロン1〜ナイロン12などのポリアミド類;
脂肪族ポリエステル、芳香族ポリエステル、脂環族ポリエステル、ポリ炭酸エステル、アルキド樹脂などのポリエステル類;
ポリ尿素類;ポリスルホン類;ポリアジン類;ポリアミン類;ポリ芳香族ケトン類;
ポリイミド類;ポリベンゾイミダゾール類;ポリベンゾオキサゾール類;
ポリベンゾチアゾール類;ポリアミノトリアゾール類;ポリオキサジアゾール類;
ポリピラゾール類;ポリテトラゾール類;ポリキノキサリン類;ポリトリアジン類;
ポリベンゾオキサジノン類;ポリキノリン類;ポリアントラゾリン類などが挙げられる。これらの熱可塑性樹脂は1種単独でまたは2種以上を混合して使用できる。
Examples of thermoplastic resins include polyethylene, polypropylene, poly-1-butene, poly-1-pentene, poly-1-hexene, poly-1-heptene, poly-1-octene, poly-1-decene, poly- Α-olefin polymers such as 1-dodecene, poly-1-tetradecene, poly-1-hexadecene, poly-1-octadecene, polyvinylcycloalkane;
Α, β-unsaturated aldehyde polymers such as poly-1,4-pentadiene, poly-1,4-hexadiene, poly-1,5-hexadiene, poly-1,7-o-chloroacrolein; polymethylvinyl Α, β-unsaturated ketone polymers such as ketones, polyaromatic vinyl ketones and polycyclic vinyl ketones;
Polymers of α, β-unsaturated acid derivatives such as poly (meth) acrylic acid, salts of poly (meth) acrylic acid, esters of poly (meth) acrylic acid, halides of poly (meth) acrylic acid;
Polymers of α, β-unsaturated acid anhydrides such as poly (meth) acrylic anhydride, polymaleic anhydride;
Unsaturated polybasic acid ester polymers such as polymethylenemalonic acid diester and polyitaconic acid diester;
Diolefinic acid ester polymers such as polysorbic acid ester and muconic acid ester;
Α, β-unsaturated acid thioester polymers such as polyacrylic acid thioester, methacrylic acid thioester, α-chloroacrylic acid thioester;
Polymers of acrylonitrile derivatives such as polyacrylonitrile and polymethacrylonitrile;
Polymers of acrylamide derivatives such as polyacrylamide and polymethacrylamide;
Styryl metal compound polymers; polyvinyloxy metal compounds; polyimines;
Polyethers such as polyphenylene oxide, poly-1,3-dioxolane, polyoxirane, polytetrahydrofuran, polytetrahydropyran;
Polysulfides; polysulfonamides; polypeptides;
Polyamides such as nylon 66 and nylon 1 to nylon 12;
Polyesters such as aliphatic polyester, aromatic polyester, alicyclic polyester, polycarbonate, alkyd resin;
Polyureas; polysulfones; polyazines; polyamines; polyaromatic ketones;
Polyimides; polybenzimidazoles; polybenzoxazoles;
Polybenzothiazoles; polyaminotriazoles; polyoxadiazoles;
Polypyrazoles; polytetrazoles; polyquinoxalines; polytriazines;
Polybenzoxazinones; polyquinolines; polyanthrazolins and the like. These thermoplastic resins can be used individually by 1 type or in mixture of 2 or more types.
バインダー樹脂(F)としては、このような熱可塑性樹脂の他に、レジストとのインターミキシングを防止するために、組成物を基板に塗布した後、加熱により硬化して溶剤に対して不溶となる熱硬化性樹脂も好ましく用いられる。 As the binder resin (F), in addition to such a thermoplastic resin, in order to prevent intermixing with a resist, the composition is applied to a substrate and then cured by heating to become insoluble in a solvent. A thermosetting resin is also preferably used.
このような熱硬化性樹脂としては、たとえば,熱硬化性アクリル系樹脂、フェノール樹脂、尿素樹脂、メラミン樹脂、アミノ系樹脂、芳香族炭化水素樹脂、エポキシ樹脂、アルキド樹脂などが挙げられる。これらは1種単独でまたは2種以上を混合して使用できる。 Examples of such thermosetting resins include thermosetting acrylic resins, phenol resins, urea resins, melamine resins, amino resins, aromatic hydrocarbon resins, epoxy resins, alkyd resins, and the like. These can be used individually by 1 type or in mixture of 2 or more types.
これらバインダー樹脂(F)の配合量は、上記重合体100重量部当り、通常20重量部以下、好ましくは10重量部以下である。 The blending amount of these binder resins (F) is usually 20 parts by weight or less, preferably 10 parts by weight or less per 100 parts by weight of the polymer.
(G)放射線吸収剤
放射線吸収剤(G)としては、各種の放射線吸収性を有する化合物を使用することができる。
(G) Radiation absorber As a radiation absorber (G), the compound which has various radiation absorptivity can be used.
たとえば、油溶性染料、分散染料、塩基性染料、メチン系染料、ピラゾール系染料、イミダゾール系染料、ヒドロキシアゾ系染料などの染料;ビクシン誘導体、ノルビクシン、スチルベン、4、4’−ジアミノスチルベン誘導体、クマリン誘導体、ピラゾリン誘導体などの蛍光増白剤;ヒドロキシアゾ系染料、チヌビン234(商品名、チバガイギー製)
、チヌビン1130(商品名、チバガイギー製)などの紫外線吸収剤;アントラセン誘導体、アントラキノン誘導体などの芳香族化合物などが挙げられる。
For example, oil-soluble dyes, disperse dyes, basic dyes, methine dyes, pyrazole dyes, imidazole dyes, hydroxyazo dyes and the like; bixin derivatives, norbixin, stilbene, 4,4'-diaminostilbene derivatives, coumarins Derivatives, pyrazoline derivatives and other brightening agents; hydroxyazo dyes, tinuvin 234 (trade name, manufactured by Ciba Geigy)
UV absorbers such as Tinuvin 1130 (trade name, manufactured by Ciba Geigy); aromatic compounds such as anthracene derivatives and anthraquinone derivatives.
これらの放射線吸収剤は1種単独でまたは2種以上を組み合わせて使用することができる。放射線吸収剤(G)の配合量は、反射防止膜形成用組成物の固形分100重量部当たり、通常100重量部以下、好ましくは50重量部以下である。 These radiation absorbers can be used alone or in combination of two or more. The blending amount of the radiation absorber (G) is usually 100 parts by weight or less, preferably 50 parts by weight or less, per 100 parts by weight of the solid content of the composition for forming an antireflection film.
(H)界面活性剤
本発明では、塗布性、ストリエーション、濡れ性、現像性などを改良するために、反射防止膜形成用組成物に界面活性剤(H)を添加してもよい。
(H) Surfactant In the present invention, a surfactant (H) may be added to the composition for forming an antireflection film in order to improve coatability, striation, wettability, developability and the like.
界面活性剤(H)としては、たとえば、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンオクチルフェニルエーテル、ポリオキシエチレンノニルフェニルエーテル、ポリエチレングリコールジラウレート、ポリエチレングリコールジステアレートなどのノニオン系界面活性剤が挙げられる。 Examples of the surfactant (H) include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene octyl phenyl ether, polyoxyethylene nonyl phenyl ether, polyethylene glycol dilaurate, polyethylene glycol diester. Nonionic surfactants such as stearate can be mentioned.
また、オルガノシロキサンポリマーであるKP341(商品名、信越化学工業(株)製)、(メタ)アクリル酸系(共)重合体であるポリフローNo.75、同No.95(以上、商品名、共栄社油脂化学工業製)、エフトップEF101、同EF204、同EF303、同EF352(以上、商品名、トーケムプロダクツ製)、メガファックF171、同F172、同F173(以上、商品名、大日本インキ化学工業製)、フロラードFC430、同FC431、同FC135、同FC93(以上、商品名、住友スリーエム製)、アサヒガードAG710、サーフロンS382、同SC101、同SC102、同SC103、同SC104、同SC105、同SC106(以上、商品名、旭硝子製)などの市販の界面活性剤を使用することもできる。 Further, KP341 (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.) which is an organosiloxane polymer, Polyflow No. which is a (meth) acrylic acid-based (co) polymer. 75, no. 95 (above, trade name, manufactured by Kyoeisha Yushi Chemical Co., Ltd.), EFTOP EF101, EF204, EF303, EF352 (above, tradename, manufactured by Tochem Products), MegaFuck F171, F172, F173 (above, (Trade name, manufactured by Dainippon Ink & Chemicals, Inc.), FLORARD FC430, FC431, FC135, FC135 (above, product name, manufactured by Sumitomo 3M), Asahi Guard AG710, Surflon S382, SC101, SC102, SC103, Commercially available surfactants such as SC104, SC105, and SC106 (above, trade name, manufactured by Asahi Glass Co., Ltd.) can also be used.
これらの界面活性剤は1種単独でも2種以上を組合わせても使用することができる。界面活性剤(H)の配合量は、反射防止膜形成用組成物の固形分100重量部当たり、通常15重量部以下、好ましくは10重量部以下である。 These surfactants can be used singly or in combination of two or more. The compounding amount of the surfactant (H) is usually 15 parts by weight or less, preferably 10 parts by weight or less per 100 parts by weight of the solid content of the composition for forming an antireflection film.
〔反射防止膜〕
本発明に係る反射防止膜は、上記反射防止膜形成用組成物(以下、「本発明に係る組成物」ともいう)を用いて、たとえば、下記の工程(I)〜(V)を含む方法により製造することができる。
[Antireflection film]
The antireflection film according to the present invention is, for example, a method comprising the following steps (I) to (V) using the above antireflection film forming composition (hereinafter also referred to as “the composition according to the present invention”). Can be manufactured.
<反射防止膜の製造方法および使用方法>
本発明に係る反射防止膜の製造方法は、通常、
(I)基板上に本発明に係る組成物を塗布し、得られた塗膜を硬化させて反射防止膜を形成する工程、
(II)上記反射防止膜上に溶液状のレジスト用組成物を塗布し、得られた塗膜をプレベークしてレジスト被膜を形成する工程、
(III)フォトマスクを介して上記レジスト被膜を選択的に露光する工程、
(IV)露光したレジスト被膜を現像する工程、および
(V)上記反射防止膜をエッチングする工程
を含む。
<Method for producing and using antireflection film>
The method for producing an antireflection film according to the present invention usually comprises:
(I) a step of applying the composition according to the present invention on a substrate and curing the obtained coating film to form an antireflection film;
(II) applying a solution resist composition on the antireflection film, and prebaking the obtained coating film to form a resist film;
(III) a step of selectively exposing the resist film through a photomask;
(IV) a step of developing the exposed resist film, and (V) a step of etching the antireflection film.
(I)反射防止膜形成工程:
まず、本発明に係る組成物を、回転塗布、流延塗布、ロール塗布などの公知の方法により基板上に塗布する。基板としては、たとえば、シリコンウエハー、アルミニウムで被覆
したウエハーなどを使用することができる。
(I) Antireflection film forming step:
First, the composition according to the present invention is applied onto a substrate by a known method such as spin coating, cast coating, or roll coating. As the substrate, for example, a silicon wafer, a wafer coated with aluminum, or the like can be used.
次に、塗布した組成物(塗膜)を、露光および/または加熱することにより硬化させる。露光により塗膜を硬化させる場合、照射する放射線は、使用する光酸発生剤の種類に応じて、可視光線、紫外線、遠紫外線、X線、電子線、γ線、分子線、イオンビームなどから適宜選択される。光酸発生剤を含有する組成物を使用し、かつ露光により塗膜を硬化させる場合には、常温でも塗膜を有効に硬化させることが可能である。加熱により塗膜を硬化させる場合、加熱温度は通常90〜350℃程度、好ましくは150〜350℃程度である。 Next, the applied composition (coating film) is cured by exposure and / or heating. When curing the coating film by exposure, the radiation to be irradiated is from visible light, ultraviolet light, far ultraviolet light, X-ray, electron beam, gamma ray, molecular beam, ion beam, etc., depending on the type of photoacid generator used. It is selected appropriately. When a composition containing a photoacid generator is used and the coating film is cured by exposure, the coating film can be effectively cured even at room temperature. When the coating film is cured by heating, the heating temperature is usually about 90 to 350 ° C, preferably about 150 to 350 ° C.
このようにして形成された反射防止膜の膜厚は、通常0.1〜5μmである。 The film thickness of the antireflection film thus formed is usually 0.1 to 5 μm.
(II)レジスト被膜形成工程:
工程(I)で形成した反射防止膜上に、得られるレジスト被膜が所定の膜厚となるように、溶液状のレジスト用組成物を塗布する。本発明に係る反射防止膜を用いることによって、インターミキシングを発生させることなく、レジスト被膜を形成することができる。
(II) Resist film formation process:
A resist composition in the form of a solution is applied onto the antireflection film formed in step (I) so that the resulting resist film has a predetermined thickness. By using the antireflection film according to the present invention, a resist film can be formed without causing intermixing.
レジスト用組成物としては、たとえば、光酸発生剤を含有するポジ型またはネガ型の化学増幅型レジスト用組成物、アルカリ可溶性樹脂とキノンジアジド系感光剤とからなるポジ型レジスト用組成物、アルカリ可溶性樹脂と架橋剤とからなるネガ型レジスト用組成物、シリコン含有レジスト用組成物などを挙げることができる。これらのうち、反射防止膜エッチング工程(V)において、エッチング選択性を向上させるため、シリコン含有レジスト用組成物が好ましい。このようなレジスト用組成物は溶液の状態で塗布され、その固形分濃度は通常5〜50重量%程度である。このような溶液状のレジスト用組成物は、通常、たとえば孔径0.2μm程度のフィルターでろ過した後、レジスト被膜の形成に使用する。また、市販の溶液状のレジスト用組成物をそのまま使用することもできる。 Examples of the resist composition include a positive or negative chemically amplified resist composition containing a photoacid generator, a positive resist composition comprising an alkali-soluble resin and a quinonediazide-based photosensitizer, and an alkali-soluble composition. Examples thereof include a negative resist composition comprising a resin and a crosslinking agent, and a silicon-containing resist composition. Among these, a silicon-containing resist composition is preferable in order to improve etching selectivity in the antireflection film etching step (V). Such a resist composition is applied in the form of a solution, and its solid content concentration is usually about 5 to 50% by weight. Such a resist composition in the form of a solution is usually used for forming a resist film after being filtered through a filter having a pore size of about 0.2 μm, for example. Moreover, a commercially available solution-form resist composition can also be used as it is.
上記のようにしてレジスト用組成物を塗布した後、プレベークして塗膜中の溶剤を揮発させることによりレジスト被膜を形成する。プレベークの温度は、使用するレジスト組成物の種類などに応じて適宜調整されるが、通常30〜200℃程度、好ましくは50〜150℃である。 After applying the resist composition as described above, a resist film is formed by pre-baking and volatilizing the solvent in the film. The pre-baking temperature is appropriately adjusted according to the type of resist composition to be used, but is usually about 30 to 200 ° C, preferably 50 to 150 ° C.
(III)露光工程:
工程(II)で形成したレジスト被膜を、フォトマスクを介して露光する。このとき、照射した放射線が基板表面で反射するが、本発明に係る反射防止膜の作用により、基板から反射した放射光が吸収される。
(III) Exposure process:
The resist film formed in the step (II) is exposed through a photomask. At this time, the irradiated radiation is reflected on the substrate surface, but the radiation reflected from the substrate is absorbed by the action of the antireflection film according to the present invention.
露光に用いられる放射線としては、レジスト組成物に使用される光酸発生剤の種類に応じて、可視光線、紫外線、遠紫外線、X線、電子線、γ線、分子線、イオンビームなどから適切に選択される。これらのうち、好ましくは遠紫外線であり、特に、KrFエキシマレーザー(248nm)、ArFエキシマレーザー(193nm)、F2エキシマレーザ
ー(波長157nm)、Kr2エキシマレーザー(波長147nm)、ArKrエキシマ
レーザー(波長134nm)、極紫外線(波長13nmなど)などが好ましい。
The radiation used for exposure is appropriate from visible light, ultraviolet light, far ultraviolet light, X-rays, electron beams, γ-rays, molecular beams, ion beams, etc., depending on the type of photoacid generator used in the resist composition. Selected. Of these, preferred is far-ultraviolet, and in particular, KrF excimer laser (248 nm), ArF excimer laser (193 nm), F 2 excimer laser (wavelength 157 nm), Kr 2 excimer laser (wavelength 147 nm), ArKr excimer laser (wavelength 134 nm), extreme ultraviolet light (wavelength 13 nm, etc.) and the like are preferable.
(IV)現像工程:
工程(III)で露光したレジスト被膜を現像し、洗浄し、乾燥することにより、所定の
レジストパターンを形成させる。解像度、パターンプロファイル、現像性などを向上させるために、露光後の現像前にポストベークを行なってもよい。
(IV) Development process:
The resist film exposed in the step (III) is developed, washed, and dried to form a predetermined resist pattern. In order to improve resolution, pattern profile, developability, etc., post-baking may be performed before development after exposure.
現像液は、使用するレジスト用組成物の種類に応じて適宜選択される。ポジ型化学増幅
型レジスト用組成物やアルカリ可溶性樹脂を含有するポジ型レジスト用組成物の場合に用いられる現像液としては、たとえば、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、珪酸ナトリウム、メタ珪酸ナトリウム、アンモニア、エチルアミン、n−プロピルアミン、ジエチルアミン、ジ−n−プロピルアミン、トリエチルアミン、メチルジエチルアミン、ジメチル・エタノールアミン、トリエタノールアミン、テトラメチルアンモニウムヒドロキシド、テトラエチルアンモニウムヒドロキシド、ピロール、ピペリジン、コリン、1,8−ジアザビシクロ[5.4.0]−7−ウンデセン、1,5−ジアザビシクロ[4.3.0]−5−ノネンなどのアルカリ性水溶液を挙げることができる。これらのアルカリ性水溶液には、水溶性有機溶剤、たとえばメタノール、エタノールなどのアルコール類や、界面活性剤を適量添加することもできる。
The developer is appropriately selected according to the type of resist composition used. Examples of the developer used in the case of a positive chemically amplified resist composition or a positive resist composition containing an alkali-soluble resin include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, and metasilicic acid. Sodium, ammonia, ethylamine, n-propylamine, diethylamine, di-n-propylamine, triethylamine, methyldiethylamine, dimethylethanolamine, triethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, pyrrole, piperidine, choline , 1,8-diazabicyclo [5.4.0] -7-undecene, 1,5-diazabicyclo [4.3.0] -5-nonene, and the like. An appropriate amount of a water-soluble organic solvent, for example, an alcohol such as methanol or ethanol, or a surfactant can be added to these alkaline aqueous solutions.
(V)エッチング工程:
工程(IV)で得られたレジストパターンをマスクとして、たとえば、酸素プラズマなどのガスプラズマを用いて、反射防止膜の乾式エッチングを行い、所定の基板加工用のレジストパターンを形成する。
(V) Etching process:
Using the resist pattern obtained in step (IV) as a mask, dry etching of the antireflection film is performed using, for example, gas plasma such as oxygen plasma to form a resist pattern for processing a predetermined substrate.
本発明に係る反射防止膜は、この乾式エッチングに対する耐性にも優れていることから、解像度および精度などに優れたレジストパターンを形成することができる。 Since the antireflection film according to the present invention is excellent in resistance to this dry etching, a resist pattern excellent in resolution and accuracy can be formed.
[実施例]
以下、本発明を実施例により説明するが、本発明は、この実施例により何ら限定されるものではない。また、「部」および「%」は特記しない限り、それぞれ「重量部」および「重量%」を表す。まず、本実施例で使用した評価方法を説明する。
[Example]
EXAMPLES Hereinafter, although an Example demonstrates this invention, this invention is not limited at all by this Example. “Parts” and “%” represent “parts by weight” and “% by weight”, respectively, unless otherwise specified. First, the evaluation method used in this example will be described.
<評価方法>
(分子量測定)
得られた重合体の重量平均分子量(Mw)は、東ソー社製GPCカラム(G2000HXL:2本、G3000HXL:1本)を用い、流量:1.0ml/分、溶出溶剤:テトラヒドロフラン、カラム温度:40℃の分析条件で、単分散ポリスチレンを標準とするゲルパーミエーションクロマトグラフ法(検出器:示差屈折計)により測定した。
<Evaluation method>
(Molecular weight measurement)
The weight average molecular weight (Mw) of the obtained polymer was a Tosoh GPC column (G2000HXL: 2, G3000HXL: 1), flow rate: 1.0 ml / min, elution solvent: tetrahydrofuran, column temperature: 40. The measurement was performed by gel permeation chromatography (detector: differential refractometer) using monodisperse polystyrene as a standard under analysis conditions of ° C.
(光学特性測定)
8インチのシリコンウエハー上に、反射防止膜形成用組成物をスピンコートした後、ホットプレート上で300℃で120秒間ベークして、膜厚0.3μmの反射防止膜を形成した。KLA−TENCOR社製分光エリプソメータUV−1280Eを用いて、248nmにおける屈折率(n値)および吸光度(k値)を測定した。また、SOPRA社製分光エリプソメーターMOSS−ESVG DEEP UVを用いて、193nmにおけるn値とk値を測定した。
(Optical characteristics measurement)
An antireflection film-forming composition was spin-coated on an 8-inch silicon wafer, and then baked on a hot plate at 300 ° C. for 120 seconds to form an antireflection film having a thickness of 0.3 μm. The refractive index (n value) and absorbance (k value) at 248 nm were measured using a spectroscopic ellipsometer UV-1280E manufactured by KLA-TENCOR. Moreover, the n value and k value in 193 nm were measured using the spectroscopic ellipsometer MOSS-ESVG DEEP UV by SOPRA.
〔合成例1〕
(化合物(A−1)とフラーレン化合物との重合体の合成)
温度計を備えたセパラブルフラスコに、窒素雰囲気下で、4−ヒドロキシメチルスチレンを1部と、フラーレンC60を8部と、トルエンを86.5部と、アゾビスイソブチロニトリルを4.3部とを仕込み、攪拌しながら80℃で24時間重合した。その後、反応溶液をろ紙でろ過し、ろ液を濃縮し、得られた固形物を2−ヘプタノンに再溶解させた。不溶物を再度ろ紙にてろ過し、ろ液を多量のヘキサンに再沈殿し、ろ過し、乾燥して、Mwが3,000の重合体(1)を得た。
[Synthesis Example 1]
(Synthesis of polymer of compound (A-1) and fullerene compound)
In a separable flask equipped with a thermometer, 1 part of 4-hydroxymethylstyrene, 8 parts of fullerene C 60 , 86.5 parts of toluene, and 4. 4 parts of azobisisobutyronitrile were added under a nitrogen atmosphere. 3 parts was charged and polymerized at 80 ° C. for 24 hours with stirring. Thereafter, the reaction solution was filtered with filter paper, the filtrate was concentrated, and the obtained solid was redissolved in 2-heptanone. The insoluble material was filtered again with filter paper, and the filtrate was reprecipitated in a large amount of hexane, filtered and dried to obtain a polymer (1) having an Mw of 3,000.
〔合成例2〕
(化合物(A−2)とフラーレン化合物との重合体の合成)
温度計を備えたセパラブルフラスコに、窒素雰囲気下で、アセナフチレンを3.8部と、フラーレンC60を1部と、トルエンを80部と、アゾビスイソブチロニトリルを6.4部とを仕込み、攪拌しながら90℃で12時間重合した。その後、反応溶液をろ紙でろ過し、ろ液を濃縮し、得られた固形物を2−ヘプタノンに再溶解させた。不溶物を再度ろ紙にてろ過し、ろ液を多量のヘキサンに再沈殿し、ろ過、乾燥し、Mwが3,000の重合体(2)を得た。
[Synthesis Example 2]
(Synthesis of polymer of compound (A-2) and fullerene compound)
In a separable flask equipped with a thermometer, under a nitrogen atmosphere, 3.8 parts of acenaphthylene, 1 part of fullerene C 60 , 80 parts of toluene, and 6.4 parts of azobisisobutyronitrile. The polymerization was carried out at 90 ° C. for 12 hours while charging and stirring. Thereafter, the reaction solution was filtered with filter paper, the filtrate was concentrated, and the obtained solid was redissolved in 2-heptanone. Insoluble matter was filtered again with filter paper, and the filtrate was reprecipitated in a large amount of hexane, filtered and dried to obtain a polymer (2) having an Mw of 3,000.
〔調製例1〕
(ArF用レジスト溶液の調製)
還流管を装着したセパラブルフラスコに、窒素気流下で、8−メチル−8−t−ブトキシカルボニルメトキシカルボニルテトラシクロ[4.4.0.12,5.17,10]ドデカ−
3−エン29部、8−ヒドロキシテトラシクロ[4.4.0.12,5.17,10]ドデカ−
3−エン10部、無水マレイン酸18部、2,5−ジメチル−2,5−ヘキサンジオールジアクリレート4部、t−ドデシルメルカプタン1部、アゾビスイソブチロニトリル4部および1,2−ジエトキシエタン60部を仕込み、70℃で6時間重合した。重合終了後、反応溶液を大量のn−ヘキサン/i−プロピルアルコール(重量比=1/1)混合溶液中に注いで、樹脂を凝固させた。凝固した樹脂を同一混合溶媒で数回洗浄したのち、真空乾燥して共重合体を得た。この共重合体の収率は60%であり、Mwは27,000であった。また、この共重合体は、下記式(a)、(b)および(c)で表される構成単位の含有率がそれぞれ64モル%、18モル%および18モル%であった。
[Preparation Example 1]
(Preparation of resist solution for ArF)
In a separable flask equipped with a reflux tube, 8-methyl-8-t-butoxycarbonylmethoxycarbonyltetracyclo [4.4.0.1 2,5 . 1 7,10 ] Dodeka
29 parts 3-ene, 8-hydroxytetracyclo [4.4.0.1 2,5 . 1 7,10 ] Dodeka
3-ene 10 parts, maleic anhydride 18 parts, 2,5-dimethyl-2,5-hexanediol diacrylate 4 parts, t-dodecyl mercaptan 1 part, azobisisobutyronitrile 4 parts and 1,2-di 60 parts of ethoxyethane was charged and polymerized at 70 ° C. for 6 hours. After completion of the polymerization, the reaction solution was poured into a large amount of n-hexane / i-propyl alcohol (weight ratio = 1/1) mixed solution to solidify the resin. The coagulated resin was washed several times with the same mixed solvent and then vacuum dried to obtain a copolymer. The yield of this copolymer was 60%, and Mw was 27,000. Further, in this copolymer, the contents of the structural units represented by the following formulas (a), (b) and (c) were 64 mol%, 18 mol% and 18 mol%, respectively.
(1)反射防止膜形成用組成物の調製
合成例1で調製した重合体(1)10部、サイメル300(三井サイアナミッド(株)
製)0.5部およびビス(4−t−ブチルフェニル)ヨードニウムカンファースルホネート0.5部を、2−ヘプタノン89部に溶解した。得られた溶液を孔径0.1μmのメンブランフィルターでろ過し、反射防止膜形成用組成物を調製した。
(1) Preparation of composition for formation of antireflection film 10 parts of polymer (1) prepared in Synthesis Example 1, Cymel 300 (Mitsui Cyanamid Co., Ltd.)
0.5 part) and 0.5 part of bis (4-t-butylphenyl) iodonium camphorsulfonate were dissolved in 89 parts of 2-heptanone. The obtained solution was filtered through a membrane filter having a pore size of 0.1 μm to prepare an antireflection film-forming composition.
(2)反射防止膜の形成
上記(1)で得られた組成物を、8インチのシリコンウエハー上に膜厚0.3μmの反射防止膜が得られるようにスピンコートした後、ホットプレート上で300℃で120秒間ベークして反射防止膜を形成した。
(2) Formation of antireflection film The composition obtained in (1) above was spin-coated on an 8-inch silicon wafer so as to obtain an antireflection film having a film thickness of 0.3 μm, and then on a hot plate. An antireflection film was formed by baking at 300 ° C. for 120 seconds.
(3)KrF用ポジ型レジストパターンの形成
上記(2)で得られた反射防止膜上に、KrF用レジスト溶液(商品名:KRF M20G、ジェイエスアール(株)製)を膜厚0.31μmのレジスト膜が得られるようにスピンコートした後、140℃のホットプレート上で1分間ベークし、レジスト膜を形成した。
(3) Formation of positive resist pattern for KrF On the antireflection film obtained in (2) above, a KrF resist solution (trade name: KRF M20G, manufactured by JSR Corporation) with a film thickness of 0.31 μm After spin coating to obtain a resist film, the resist film was baked on a hot plate at 140 ° C. for 1 minute to form a resist film.
次いで、ステッパーNSR2005EX12B(波長248nm、(株)ニコン製)を用いて、0.22μm幅のラインアンドスペースパターンを1対1の線幅で形成するような露光時間(以下、「最適露光時間」という。)だけ露光を行った。その後、140℃のホットプレート上で、90秒間ベークした後、2.38%テトラメチルアンモニウムヒドロキシド水溶液を用いて、23℃で30秒間現像し、水洗し、乾燥して、ポジ型レジストパターンを形成した。 Next, using a stepper NSR2005EX12B (wavelength 248 nm, manufactured by Nikon Corporation), an exposure time for forming a line-and-space pattern having a width of 0.22 μm with a one-to-one line width (hereinafter referred to as “optimum exposure time”) .) Only exposed. Then, after baking for 90 seconds on a 140 ° C. hot plate, using a 2.38% tetramethylammonium hydroxide aqueous solution, developed at 23 ° C. for 30 seconds, washed with water, and dried to form a positive resist pattern. Formed.
(4)KrF用ポジ型レジストパターンの形成
上記(2)で得られた反射防止膜上に、ArF用レジスト溶液を膜厚0.2μmのレジスト膜が得られるようにスピンコートした後、ホットプレート上で100℃で90秒間ベークし、レジスト膜を形成した。
(4) Formation of KrF positive resist pattern On the antireflection film obtained in the above (2), an ArF resist solution was spin-coated so as to obtain a 0.2 μm-thick resist film, and then hot plate The resist film was formed by baking at 100 ° C. for 90 seconds.
次いで、ArFエキシマレーザー露光装置(レンズ開口数0.60、露光波長193nm、ISI社製)により、マスクパターンを介して露光を行った。その後、ホットプレート上で140℃で90秒間ベークした後、2.38%テトラメチルアンモニウムヒドロキシド水溶液を用いて、25℃で1分間現像し、水洗し、乾燥して、ポジ型レジストパターンを形成した。 Next, exposure was performed through a mask pattern by an ArF excimer laser exposure apparatus (lens numerical aperture 0.60, exposure wavelength 193 nm, manufactured by ISI). Then, after baking at 140 ° C. for 90 seconds on a hot plate, using a 2.38% tetramethylammonium hydroxide aqueous solution, developed at 25 ° C. for 1 minute, washed with water, and dried to form a positive resist pattern. did.
(5)光学特性の測定
上記(2)で得られた反射防止膜について、分光エリプソメータUV−1280E(KLA−TENCOR社製)を用いて、248nmにおける屈折率(n値)および吸光度(k値)を測定した。また、分光エリプソメーターMOSS−ESVG DEEP UV(SOPRA社製)を用いて、193nmにおけるn値とk値を測定した。
(5) Measurement of optical characteristics About the antireflection film obtained in (2) above, a refractive index (n value) and absorbance (k value) at 248 nm using a spectroscopic ellipsometer UV-1280E (manufactured by KLA-TENCOR). Was measured. Moreover, n value and k value in 193 nm were measured using the spectroscopic ellipsometer MOSS-ESVG DEEP UV (made by SOPRA).
(6)インターミキシング防止効果の評価
上記(3)および(4)で形成したレジストパターンそれぞれについて、現像後に残った部分と反射防止膜との接点におけるレジスト膜の裾引きの程度を、走査型電子顕微鏡を用いて調べた。
(6) Evaluation of anti-intermixing effect For each of the resist patterns formed in the above (3) and (4), the degree of tailing of the resist film at the contact point between the portion remaining after development and the antireflection film It investigated using the microscope.
(7)定在波防止効果の評価
上記(3)および(4)で形成したレジストパターンそれぞれについて、レジストパターンへの定在波の影響(レジストパターンの側壁のガタつき)の有無を走査型電子顕微鏡を用いて調べた。
(7) Evaluation of Standing Wave Prevention Effect For each of the resist patterns formed in the above (3) and (4), the presence of the influence of the standing wave on the resist pattern (backlash of the side wall of the resist pattern) is determined by scanning electron. It investigated using the microscope.
(8)エッチング耐性評価
上記(2)で得られた反射防止膜を、エッチング装置EXAM(神鋼精機社製)を用いて、CF4/Ar/O2(CF4:40mL/min、Ar:20mL/min、O2:5mL/min;圧力:20Pa;RFパワー:200W;処理時間:40秒;温度:15℃)でエッチング処理し、処理前後の膜厚を測定して、エッチングレートを算出した。
(8) Evaluation of etching resistance The antireflection film obtained in (2) above was subjected to CF 4 / Ar / O 2 (CF 4 : 40 mL / min, Ar: 20 mL) using an etching apparatus EXAM (manufactured by Shinko Seiki) / Min, O 2 : 5 mL / min; pressure: 20 Pa; RF power: 200 W; treatment time: 40 seconds; temperature: 15 ° C.), the film thickness before and after the treatment was measured, and the etching rate was calculated. .
得られた反射防止膜およびレジストパターンを評価した結果を表1に示す。 The results of evaluating the obtained antireflection film and resist pattern are shown in Table 1.
合成例1で調製した重合体(1)の代わりに、合成例2で調製した重合体(2)10部、サイメル300の代わりにBAC−E(東洋合成工業(株)製)を用いた以外は実施例1と同様にして反射防止膜形成用組成物を調製した。この反射防止膜形成用組成物を用いて、実施例1と同様にして反射防止膜およびレジスト膜(レジストパターン)を形成し、これらを評価した。その結果を表1に示す。 10 parts of the polymer (2) prepared in Synthesis Example 2 was used instead of the polymer (1) prepared in Synthesis Example 1, and BAC-E (manufactured by Toyo Gosei Co., Ltd.) was used instead of Cymel 300. Prepared an antireflection film-forming composition in the same manner as in Example 1. Using this composition for forming an antireflection film, an antireflection film and a resist film (resist pattern) were formed in the same manner as in Example 1, and these were evaluated. The results are shown in Table 1.
[比較例1]
反射防止膜を形成せず、シリコンウエハー上にレジスト膜を形成した以外は、実施例1と同様にしてレジストパターン作製し、これらを評価した。その結果を表1に示す。
[Comparative Example 1]
Resist patterns were prepared and evaluated in the same manner as in Example 1 except that a resist film was formed on a silicon wafer without forming an antireflection film. The results are shown in Table 1.
[比較例2]
反射防止膜形成用組成物の代わりにノボラック樹脂を用いた以外は、実施例1と同様にして反射防止膜およびレジストパターンを形成し、これらを評価した。その結果を表1に示す。
[Comparative Example 2]
An antireflection film and a resist pattern were formed in the same manner as in Example 1 except that novolak resin was used instead of the composition for forming an antireflection film, and these were evaluated. The results are shown in Table 1.
本発明に係る反射防止膜形成用組成物は、ドライエッチング耐性に優れ、反射防止効果が高く、かつレジストとインターミキシングを生じることのない反射防止膜を形成できることから、高集積度の集積回路の製造に特に有用である。 The composition for forming an antireflection film according to the present invention is excellent in dry etching resistance, has a high antireflection effect, and can form an antireflection film that does not cause intermixing with a resist. It is particularly useful for manufacturing.
Claims (6)
独立に水素原子、フッ素原子または1価の基を示し、R4はハロゲン原子または1価の基
を示す) An antireflection film-forming composition comprising a polymer having a repeating unit (a-1) represented by the following formula (1) and a repeating unit (b) having a fullerene structure.
は1価の基を示す) An antireflective film-forming composition comprising a polymer having a repeating unit (a-2) represented by the following formula (2) and a repeating unit (b) having a fullerene structure.
独立に水素原子、フッ素原子または1価の基を示し、R4はハロゲン原子または1価の基
を示す)
は1価の基を示す) Selected from the group consisting of at least one compound (A-1) represented by the following formula (3) or at least one compound (A-2) represented by the following formula (4), fullerene and a fullerene derivative An antireflective film-forming composition comprising a polymer obtained by mixing at least one fullerene compound (B) and heating in the presence of a radical initiator.
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