JP6157605B2 - ポジ型感光性材料 - Google Patents
ポジ型感光性材料 Download PDFInfo
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- JP6157605B2 JP6157605B2 JP2015516525A JP2015516525A JP6157605B2 JP 6157605 B2 JP6157605 B2 JP 6157605B2 JP 2015516525 A JP2015516525 A JP 2015516525A JP 2015516525 A JP2015516525 A JP 2015516525A JP 6157605 B2 JP6157605 B2 JP 6157605B2
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- 239000000463 material Substances 0.000 title description 5
- -1 1,2-propylene group Chemical group 0.000 claims description 134
- 229920000642 polymer Polymers 0.000 claims description 93
- 239000000203 mixture Substances 0.000 claims description 60
- 229920003986 novolac Polymers 0.000 claims description 38
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 239000000758 substrate Substances 0.000 claims description 18
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 13
- 230000005855 radiation Effects 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 11
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 11
- 229930003836 cresol Natural products 0.000 claims description 10
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 10
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000003871 sulfonates Chemical class 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- LJHFIVQEAFAURQ-ZPUQHVIOSA-N (NE)-N-[(2E)-2-hydroxyiminoethylidene]hydroxylamine Chemical class O\N=C\C=N\O LJHFIVQEAFAURQ-ZPUQHVIOSA-N 0.000 claims description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical class C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- LWHOMMCIJIJIGV-UHFFFAOYSA-N (1,3-dioxobenzo[de]isoquinolin-2-yl) trifluoromethanesulfonate Chemical compound C1=CC(C(N(OS(=O)(=O)C(F)(F)F)C2=O)=O)=C3C2=CC=CC3=C1 LWHOMMCIJIJIGV-UHFFFAOYSA-N 0.000 claims description 3
- HMBHAQMOBKLWRX-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-3-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)COC2=C1 HMBHAQMOBKLWRX-UHFFFAOYSA-N 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229940075419 choline hydroxide Drugs 0.000 claims description 3
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 claims description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 2
- DYOQNXMUXLWAMT-UHFFFAOYSA-N FC(F)(C1CC2CCC1C2)C(F)(F)S(=O)(=O)ON1C(=O)c2cccc3cccc(C1=O)c23 Chemical compound FC(F)(C1CC2CCC1C2)C(F)(F)S(=O)(=O)ON1C(=O)c2cccc3cccc(C1=O)c23 DYOQNXMUXLWAMT-UHFFFAOYSA-N 0.000 claims 2
- LDQBXAADVARGKQ-UHFFFAOYSA-N (1,3-dioxobenzo[de]isoquinolin-2-yl) 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound C1=CC(C(N(OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C2=O)=O)=C3C2=CC=CC3=C1 LDQBXAADVARGKQ-UHFFFAOYSA-N 0.000 claims 1
- WVKPYYLOFMTDHB-UHFFFAOYSA-N 2-norbornyl radical Chemical group C1CC2[CH]CC1C2 WVKPYYLOFMTDHB-UHFFFAOYSA-N 0.000 claims 1
- 150000003459 sulfonic acid esters Chemical class 0.000 claims 1
- 229920002120 photoresistant polymer Polymers 0.000 description 42
- 239000000243 solution Substances 0.000 description 27
- 239000007787 solid Substances 0.000 description 26
- 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 24
- 235000012431 wafers Nutrition 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- 230000015572 biosynthetic process Effects 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 21
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 16
- 239000010949 copper Substances 0.000 description 15
- 229910052710 silicon Inorganic materials 0.000 description 15
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- 238000006116 polymerization reaction Methods 0.000 description 14
- 239000010703 silicon Substances 0.000 description 14
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 13
- 229910052802 copper Inorganic materials 0.000 description 13
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 12
- 238000004090 dissolution Methods 0.000 description 12
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 9
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 150000002989 phenols Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- YFSUTJLHUFNCNZ-UHFFFAOYSA-N perfluorooctane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YFSUTJLHUFNCNZ-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000004806 packaging method and process Methods 0.000 description 5
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- 150000001299 aldehydes Chemical class 0.000 description 4
- 238000005530 etching Methods 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000005647 linker group Chemical group 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 206010034972 Photosensitivity reaction Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000036211 photosensitivity Effects 0.000 description 3
- 238000007747 plating Methods 0.000 description 3
- XNUYPROIFFCXAE-UHFFFAOYSA-N (4-cyclohexylphenyl)-diphenylsulfanium Chemical compound C1CCCCC1C1=CC=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 XNUYPROIFFCXAE-UHFFFAOYSA-N 0.000 description 2
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 2
- MZVABYGYVXBZDP-UHFFFAOYSA-N 1-adamantyl 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2CC1(OC(=O)C(=C)C)C3 MZVABYGYVXBZDP-UHFFFAOYSA-N 0.000 description 2
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- WFQNMENFJSZTGD-UHFFFAOYSA-O 2,6-dimethyl-4-(thiolan-1-ium-1-yl)phenol Chemical compound CC1=C(O)C(C)=CC([S+]2CCCC2)=C1 WFQNMENFJSZTGD-UHFFFAOYSA-O 0.000 description 2
- WTQZSMDDRMKJRI-UHFFFAOYSA-N 4-diazoniophenolate Chemical class [O-]C1=CC=C([N+]#N)C=C1 WTQZSMDDRMKJRI-UHFFFAOYSA-N 0.000 description 2
- FFWSICBKRCICMR-UHFFFAOYSA-N 5-methyl-2-hexanone Chemical compound CC(C)CCC(C)=O FFWSICBKRCICMR-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- DPWZPTOHZTVVDP-UHFFFAOYSA-N C12C(CC(CC1)C2)C(C(S(=O)(=O)[O-])(F)F)(F)F.[SH+]2CCCC2 Chemical compound C12C(CC(CC1)C2)C(C(S(=O)(=O)[O-])(F)F)(F)F.[SH+]2CCCC2 DPWZPTOHZTVVDP-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000003935 benzaldehydes Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 150000008109 benzenetriols Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- IZJVVXCHJIQVOL-UHFFFAOYSA-N nitro(phenyl)methanesulfonic acid Chemical class OS(=O)(=O)C([N+]([O-])=O)C1=CC=CC=C1 IZJVVXCHJIQVOL-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 239000003504 photosensitizing agent Substances 0.000 description 2
- 238000012643 polycondensation polymerization Methods 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- 150000003739 xylenols Chemical class 0.000 description 2
- FMEBJQQRPGHVOR-UHFFFAOYSA-N (1-ethylcyclopentyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1(CC)CCCC1 FMEBJQQRPGHVOR-UHFFFAOYSA-N 0.000 description 1
- PNXSDOXXIOPXPY-UHFFFAOYSA-N (3,5-dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl) 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate Chemical compound C1=CC2CC1C1C2C(=O)N(OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C1=O PNXSDOXXIOPXPY-UHFFFAOYSA-N 0.000 description 1
- ZKXMOAZVGXPZFK-UHFFFAOYSA-N (3,5-dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl) 1,1-difluoro-2-(4-tetracyclo[6.2.1.13,6.02,7]dodecanyl)ethanesulfonate Chemical compound C12C3C(CC(C2C2CCC1C2)C3)CC(F)(F)S(=O)(=O)ON3C(=O)C2C1C=CC(C2C3=O)C1 ZKXMOAZVGXPZFK-UHFFFAOYSA-N 0.000 description 1
- JYPFUPZGMLOPAJ-UHFFFAOYSA-N (3,5-dioxo-4-azatricyclo[5.2.1.02,6]dec-8-en-4-yl) 2-(2-bicyclo[2.2.1]heptanyl)-1,1,2,2-tetrafluoroethanesulfonate Chemical compound C1=CC2CC1C(C1=O)C2C(=O)N1OS(=O)(=O)C(F)(F)C(F)(F)C1C(C2)CCC2C1 JYPFUPZGMLOPAJ-UHFFFAOYSA-N 0.000 description 1
- QEYKXSMQZGHJSX-UHFFFAOYSA-M (4-cyclohexylphenyl)-diphenylsulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1CCCCC1C1=CC=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=C1 QEYKXSMQZGHJSX-UHFFFAOYSA-M 0.000 description 1
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- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
- G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
感光性層を化学線で像様露光して潜像を形成し;
潜像を現像剤中で現像し、
ここで像様露光された感光性層は、任意選択的に熱処理される、
ことを含む、前記方法である。
以下の調合物例では、三種のノボラックポリマーを使用した。ノボラック−1は、m−クレゾール及びホルムアルデヒドから合成し、2.38%水性TMAH現像剤中で700Å/秒のバルク溶解速度を有した。ノボラック−2は、m−クレゾール及びホルムアルデヒドから合成し、2.38%水性TMAH現像剤中で1,600Å/秒のバルク溶解速度を有した。ノボラック−3は、ノボラック−1とノボラック−2の1/1ブレンドであり、2.38%水性TMAH現像剤中で1,000Å/秒のバルク溶解速度を有した。
コーティング:全ての調合物は、8インチ径のSi及びCuウェハ上で試験した。Siウェハは脱水ベークし、そしてヘキサメチルジシラザン(HMDS)で蒸気下地処理した。Cuウェハは、5,000オングストロームの二酸化ケイ素、250オングストロームの窒化タンタル、および3,500オングストロームのCu(PVD蒸着)でコーティングしたケイ素ウェハであった。
本願は特許請求の範囲に記載の発明に係るものであるが、本願の開示は以下も包含する:
1.
a)少なくとも一種の光酸発生剤;
b)少なくとも一種のノボラックポリマー;
c)ポリマー主鎖を有する少なくとも一種のポリマー、ここで前記ポリマーは、次の式の構造を含む、ポジ作動型感光性組成物。
2.
少なくとも一種の光酸発生剤が、オニウム塩、ジカルボキシイミジルスルホネートエステル、オキシムスルホネートエステル、ジアゾ(スルホニルメチル)化合物、ジスルホニルメチレンヒドラジン化合物、ニトロベンジルスルホネートエステル、ビイミダゾール化合物、ジアゾメタン誘導体、グリオキシム誘導体、β−ケトスルホン誘導体、ジスルホン誘導体、スルホン酸エステル誘導体、イミドイルスルホネート誘導体、またはハロゲン化トリアジン化合物である、上記1に記載のポジ作動型感光性材料。
3.
少なくとも一種のノボラックポリマーが、o−クレゾール、p−クレゾールまたはm−クレゾールから選択される一種以上のクレゾール系繰り返し単位を含む、上記1または2に記載のポジ作動型感光性組成物。
4.
少なくとも一種のノボラックポリマーが、少なくとも80モル%のm−クレゾールを含むクレゾール系ノボラックである、上記3に記載のポジ作動型感光性材料。
5.
Aが、メチレン基、エチレン基または1,2−プロピレン基であり、そしてBがメチル基、エチル基、プロピル基またはブチル基である、上記1〜4のいずれか一つに記載のポジ作動型感光性組成物。
6.
Gが酸解裂性基である、上記1〜5のいずれか一つに記載のポジ作動型感光性組成物。
7.
Gが、t−ブチル基、テトラヒドロピラン−2−イル基、テトラヒドロフラン−2−イル基、4−メトキシテトラヒドロピラン−4−イル基、1−エトキシエチル基、1−ブトキシエチル基、1−プロポキシエチル基、3−オキソシクロヘキシル基、2−メチル−2−アダマンチル基、2−エチル−2−アダマンチル基、8−メチル−8−トリシクロ[5.2.1.0 2,6]デシル基、1,2,7,7−テトラメチル−2−ノルボニル基、2−アセトキシメンチル基、2−ヒドロキシメチル基、1−メチル−1−シクロヘキシルエチル基、4−メチル−2−オキソテトラヒドロ−2H−ピラン−4−イル基、2,3−ジメチルブタン−2−イル基、2,3,3−トリメチルブタン−2−イル基、1−メチルシクロペンチル基、1−エチルシクロペンチル基、1−メチルシクロヘキシル基、1−エチルシクロヘキシル基、1,2,3,3−テトラメチルビシクロ[2.2.1]ヘプタン−2−イル基、2−エチル−1,3,3−トリメチルビシクロ[2.2.1]ヘプタン−2−イル基、2,6,6−トリメチルビシクロ[3.1.1]ヘプタン−2−イル基、2,3−ジメチルペンタン−3−イル基、または3−エチル−2−メチルペンタン−3−イル基から選択される酸解裂性基である、上記1〜5のいずれか一つに記載のポジ作動型感光性組成物。
8.
Aが、メチレン基、エチレン基または1,2−プロピレン基であり、Dが、−COOCH 2 −または−COO−基であり、そしてArが、フェニルまたはヒドロキシフェニル基である、上記1〜7のいずれか一つに記載のポジ作動型感光性組成物。
9.
Eが1,2−プロピレン基である、上記1〜8のいずれか一つに記載のポジ作動型感光性組成物。
10.
ポジ型レリーフ画像を形成する方法であって、
a)上記1〜9のいずれか一つに記載のポジ作動型感光性組成物を基材上に施与することによって感光性層を形成し、
b)感光性層を化学線に像様露光して潜像を形成し、
c)潜像を現像剤中で現像し、
d)任意選択的に、前記像様露光された感光性層を熱処理する、
ことを含む、前記方法。
11.
現像剤が、テトラ(C 1 〜C 4 アルキル)アンモニウムヒドロキシド、コリンヒドロキシド、水酸化リチウム、水酸化ナトリウムまたは水酸化カリウムから選択される少なくとも一種の化合物を含む、請求項10に記載の方法。
12.
化学線の波長が約240nm〜約450nmである、請求項10または11に記載の方法。
Claims (18)
- a)少なくとも一種の光酸発生剤;
b)o−クレゾール、p−クレゾールまたはm−クレゾールから選択される一種以上のクレゾール系繰り返し単位を含む、少なくとも一種のノボラックポリマー;
c)ポリマー主鎖を有する少なくとも一種のポリマー、ここで前記ポリマーは、次の式の構造からなる、ポジ作動型感光性組成物。
- 少なくとも一種の光酸発生剤が、オニウム塩、ジカルボキシイミジルスルホネートエステル、オキシムスルホネートエステル、ジアゾ(スルホニルメチル)化合物、ジスルホニルメチレンヒドラジン化合物、ニトロベンジルスルホネートエステル、ビイミダゾール化合物、ジアゾメタン誘導体、グリオキシム誘導体、β−ケトスルホン誘導体、ジスルホン誘導体、スルホン酸エステル誘導体、イミドイルスルホネート誘導体、またはハロゲン化トリアジン化合物である、請求項1に記載のポジ作動型感光性組成物。
- 少なくとも一種のノボラックポリマーが、p−クレゾールまたはm−クレゾールから選択される一種以上のクレゾール系繰り返し単位を含む、請求項1または2に記載のポジ作動型感光性組成物。
- 少なくとも一種のノボラックポリマーが、少なくとも80モル%のm−クレゾールを含むクレゾール系ノボラックである、請求項3に記載のポジ作動型感光性組成物。
- Aが、エチレン基であり、そしてBがメチル基、エチル基、プロピル基またはブチル基である、請求項1〜4のいずれか一つに記載のポジ作動型感光性組成物。
- Gが、t−ブチル基、テトラヒドロピラン−2−イル基、テトラヒドロフラン−2−イル基、4−メトキシテトラヒドロピラン−4−イル基、1−エトキシエチル基、1−ブトキシエチル基、1−プロポキシエチル基、3−オキソシクロヘキシル基、2−メチル−2−アダマンチル基、2−エチル−2−アダマンチル基、8−メチル−8−トリシクロ[5.2.1.0 2,6]デシル基、1,2,7,7−テトラメチル−2−ノルボニル基、2−アセトキシメンチル基、2−ヒドロキシメチル基、1−メチル−1−シクロヘキシルエチル基、4−メチル−2−オキソテトラヒドロ−2H−ピラン−4−イル基、2,3−ジメチルブタン−2−イル基、2,3,3−トリメチルブタン−2−イル基、1−メチルシクロペンチル基、1−エチルシクロペンチル基、1−メチルシクロヘキシル基、1−エチルシクロヘキシル基、1,2,3,3−テトラメチルビシクロ[2.2.1]ヘプタン−2−イル基、2−エチル−1,3,3−トリメチルビシクロ[2.2.1]ヘプタン−2−イル基、2,6,6−トリメチルビシクロ[3.1.1]ヘプタン−2−イル基、2,3−ジメチルペンタン−3−イル基、及び3−エチル−2−メチルペンタン−3−イル基からなる群から選択される酸解裂性基である、請求項1〜5のいずれか一つに記載のポジ作動型感光性組成物。
- Gが、t−ブチル基、2−メチル−2−アダマンチル基、2−エチル−2−アダマンチル基、8−メチル−8−トリシクロ[5.2.1.0 2,6]デシル基、1,2,7,7−テトラメチル−2−ノルボニル基、2−アセトキシメンチル基、1−メチル−1−シクロヘキシルエチル基、2,3−ジメチルブタン−2−イル基、2,3,3−トリメチルブタン−2−イル基、1−メチルシクロペンチル基、1−エチルシクロペンチル基、1−メチルシクロヘキシル基、1−エチルシクロヘキシル基、1,2,3,3−テトラメチルビシクロ[2.2.1]ヘプタン−2−イル基、2−エチル−1,3,3−トリメチルビシクロ[2.2.1]ヘプタン−2−イル基、2,6,6−トリメチルビシクロ[3.1.1]ヘプタン−2−イル基、2,3−ジメチルペンタン−3−イル基、または3−エチル−2−メチルペンタン−3−イル基から選択される酸解裂性基である、請求項1〜5のいずれか一つに記載のポジ作動型感光性組成物。
- Aが、エチレン基であり、及びDが、−COOCH 2 −である、請求項1〜7のいずれか一つに記載のポジ作動型感光性組成物。
- yが>0モル%の時、Eが1,2−プロピレン基である、請求項1〜8のいずれか一つに記載のポジ作動型感光性組成物。
- ポリマーの構造式において、vが3モル%〜8モル%である、請求項1〜9のいずれか一つに記載のポジ作動型感光性組成物。
- ポリマーの構造式において、vが4モル%〜6モル%であり、wが9モル%〜12モル%であり、及びyが28モル%〜33モル%である、請求項1〜10のいずれか一つに記載のポジ作動型感光性組成物。
- ポリマーの構造式において、wが9モル%〜12モル%であり、及びyが28モル%〜33モル%である、請求項1〜11のいずれか一つに記載のポジ作動型感光性組成物。
- 光酸発生剤が、ジカルボキシイミジルスルホネートエステル、オキシムスルホネートエステル、ジアゾ(スルホニルメチル)化合物、ジスルホニルメチレンヒドラジン化合物、ニトロベンジルスルホネートエステル、ビイミダゾール化合物、ジアゾメタン誘導体、グリオキシム誘導体、β−ケトスルホン誘導体、ジスルホン誘導体、スルホン酸エステル誘導体、イミドイルスルホネート誘導体、及びハロゲン化されたトリアジン化合物からなる群から選択される、請求項1〜12のいずれか一つに記載のポジ作動型感光性組成物。
- イミドイルスルホネート誘導体が、1,3−ジオキソイソインドリン−2−イルトリフルオロメタンスルホネート、1,3−ジオキソイソインドリン−2−イルノナフルオロ−n−ブタンスルホネート、1,3−ジオキソイソインドリン−2−イルパーフルオロ−n−オクタンスルホネート、3−ジオキソイソインドリン−2−イル2−(ビシクロ[2.2.1]ヘプタン−2−イル)−1,1,2,2−テトラフルオロエタンスルホネート、3−ジオキソイソインドリン−2−イルN−[2−(テトラシクロ[4.4.0.1 2,5 .1 7,10 ]ドデカン−3−イル)−1,1−ジフルオロエタンスルホネート、1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イルトリフルオロメタンスルホネート、1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イルノナフルオロ−n−ブタンスルホネート、1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イルパーフルオロ−n−オクタンスルホネート、1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イル2−(ビシクロ[2.2.1]ヘプタン−2−イル)−1,1,2,2−テトラフルオロエタンスルホネート、及び1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イルN−[2−(テトラシクロ[4.4.0.1 2,5 .1 7,10 ]ドデカン−3−イル)−1,1−ジフルオロエタンスルホネートからなる群から選択される、請求項13に記載のポジ作動型感光性組成物。
- イミドイルスルホネート誘導体が、1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イルトリフルオロメタンスルホネート、1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イルノナフルオロ−n−ブタンスルホネート、1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イルパーフルオロ−n−オクタンスルホネート、1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イル2−(ビシクロ[2.2.1]ヘプタン−2−イル)−1,1,2,2−テトラフルオロエタンスルホネート、及び1,3−ジオキソ−1H−ベンゾ[de]イソキノリン−2(3H)−イルN−[2−(テトラシクロ[4.4.0.1 2,5 .1 7,10 ]ドデカン−3−イル)−1,1−ジフルオロエタンスルホネートからなる群から選択される、請求項13に記載のポジ作動型感光性組成物。
- ポジ型レリーフ画像を形成する方法であって、
a)請求項1〜15のいずれか一つに記載のポジ作動型感光性組成物を基材上に施与することによって感光性層を形成し、
b)感光性層を化学線に像様露光して潜像を形成し、
c)潜像を現像剤中で現像し、
d)任意選択的に、前記像様露光された感光性層を熱処理する、
ことを含む、前記方法。 - 現像剤が、テトラ(C1〜C4アルキル)アンモニウムヒドロキシド、コリンヒドロキシド、水酸化リチウム、水酸化ナトリウムまたは水酸化カリウムから選択される少なくとも一種の化合物を含む、請求項16に記載の方法。
- 化学線の波長が約240nm〜約450nmである、請求項16または17に記載の方法。
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US13/524,790 US9012126B2 (en) | 2012-06-15 | 2012-06-15 | Positive photosensitive material |
PCT/EP2013/059771 WO2013185989A1 (en) | 2012-06-15 | 2013-05-13 | Positive photosensitive material |
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US8906594B2 (en) | 2012-06-15 | 2014-12-09 | Az Electronic Materials (Luxembourg) S.A.R.L. | Negative-working thick film photoresist |
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US20130337380A1 (en) | 2013-12-19 |
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CN104380198B (zh) | 2018-09-21 |
TWI569102B (zh) | 2017-02-01 |
SG11201407090XA (en) | 2014-11-27 |
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