WO2010059174A1 - Metal compositions and methods of making same - Google Patents
Metal compositions and methods of making same Download PDFInfo
- Publication number
- WO2010059174A1 WO2010059174A1 PCT/US2009/003841 US2009003841W WO2010059174A1 WO 2010059174 A1 WO2010059174 A1 WO 2010059174A1 US 2009003841 W US2009003841 W US 2009003841W WO 2010059174 A1 WO2010059174 A1 WO 2010059174A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- metal
- group
- containing composition
- photosensitive
- photosensitive metal
- Prior art date
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- 229910052751 metal Inorganic materials 0.000 title claims abstract description 191
- 239000002184 metal Substances 0.000 title claims abstract description 191
- 239000000203 mixture Substances 0.000 title claims abstract description 159
- 238000000034 method Methods 0.000 title claims abstract description 93
- 230000008569 process Effects 0.000 claims abstract description 72
- 239000000758 substrate Substances 0.000 claims abstract description 28
- 238000001035 drying Methods 0.000 claims abstract description 26
- 230000005855 radiation Effects 0.000 claims abstract description 23
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 56
- -1 oxy, thio Chemical group 0.000 claims description 41
- 125000000524 functional group Chemical group 0.000 claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000003054 catalyst Substances 0.000 claims description 24
- 229910052738 indium Inorganic materials 0.000 claims description 24
- 239000002243 precursor Substances 0.000 claims description 23
- 239000003446 ligand Substances 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 19
- 229910052710 silicon Inorganic materials 0.000 claims description 19
- 239000010703 silicon Substances 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 18
- 229910052735 hafnium Inorganic materials 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 239000010936 titanium Substances 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- 239000010955 niobium Substances 0.000 claims description 15
- 239000011593 sulfur Substances 0.000 claims description 15
- 229910052715 tantalum Inorganic materials 0.000 claims description 15
- 229910052719 titanium Inorganic materials 0.000 claims description 15
- 229910052785 arsenic Inorganic materials 0.000 claims description 14
- 239000011575 calcium Substances 0.000 claims description 14
- 239000011701 zinc Substances 0.000 claims description 14
- 229910052758 niobium Inorganic materials 0.000 claims description 13
- 229910052726 zirconium Inorganic materials 0.000 claims description 13
- 229910052693 Europium Inorganic materials 0.000 claims description 12
- 229910052779 Neodymium Inorganic materials 0.000 claims description 12
- 229910052782 aluminium Inorganic materials 0.000 claims description 12
- 229910052732 germanium Inorganic materials 0.000 claims description 12
- 229910052748 manganese Inorganic materials 0.000 claims description 12
- 229910052716 thallium Inorganic materials 0.000 claims description 12
- 229910052720 vanadium Inorganic materials 0.000 claims description 12
- 229910052727 yttrium Inorganic materials 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 11
- 229910052788 barium Inorganic materials 0.000 claims description 11
- 229910052791 calcium Inorganic materials 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 229910052697 platinum Inorganic materials 0.000 claims description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 10
- 229910052787 antimony Inorganic materials 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052802 copper Inorganic materials 0.000 claims description 10
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 10
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 229910052742 iron Inorganic materials 0.000 claims description 10
- 229910052745 lead Inorganic materials 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
- 229910052763 palladium Inorganic materials 0.000 claims description 9
- 229910052718 tin Inorganic materials 0.000 claims description 9
- 229910052725 zinc Inorganic materials 0.000 claims description 9
- 229910052772 Samarium Inorganic materials 0.000 claims description 8
- 229910052804 chromium Inorganic materials 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 239000002105 nanoparticle Substances 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 229910002651 NO3 Inorganic materials 0.000 claims description 5
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 5
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical group O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 5
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims description 5
- 150000001540 azides Chemical class 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 5
- YASNYMOWPQKVTK-UHFFFAOYSA-N diarsane Chemical compound [AsH2][AsH2] YASNYMOWPQKVTK-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 5
- 125000004001 thioalkyl group Chemical group 0.000 claims description 5
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 5
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 4
- MRELNEQAGSRDBK-UHFFFAOYSA-N lanthanum(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[La+3].[La+3] MRELNEQAGSRDBK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000377 silicon dioxide Substances 0.000 claims description 4
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910004613 CdTe Inorganic materials 0.000 claims description 2
- 241000588731 Hafnia Species 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- 229910052980 cadmium sulfide Inorganic materials 0.000 claims description 2
- UHYPYGJEEGLRJD-UHFFFAOYSA-N cadmium(2+);selenium(2-) Chemical compound [Se-2].[Cd+2] UHYPYGJEEGLRJD-UHFFFAOYSA-N 0.000 claims description 2
- AOWKSNWVBZGMTJ-UHFFFAOYSA-N calcium titanate Chemical compound [Ca+2].[O-][Ti]([O-])=O AOWKSNWVBZGMTJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000011161 development Methods 0.000 claims description 2
- CJNBYAVZURUTKZ-UHFFFAOYSA-N hafnium(IV) oxide Inorganic materials O=[Hf]=O CJNBYAVZURUTKZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910000484 niobium oxide Inorganic materials 0.000 claims description 2
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 claims description 2
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 claims description 2
- UKDIAJWKFXFVFG-UHFFFAOYSA-N potassium;oxido(dioxo)niobium Chemical compound [K+].[O-][Nb](=O)=O UKDIAJWKFXFVFG-UHFFFAOYSA-N 0.000 claims description 2
- GROMGGTZECPEKN-UHFFFAOYSA-N sodium metatitanate Chemical compound [Na+].[Na+].[O-][Ti](=O)O[Ti](=O)O[Ti]([O-])=O GROMGGTZECPEKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- 229910001930 tungsten oxide Inorganic materials 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 150000001925 cycloalkenes Chemical class 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 238000010884 ion-beam technique Methods 0.000 claims 1
- 239000000463 material Substances 0.000 description 25
- 239000000243 solution Substances 0.000 description 24
- 238000000576 coating method Methods 0.000 description 13
- 238000000151 deposition Methods 0.000 description 11
- 235000012431 wafers Nutrition 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 230000008021 deposition Effects 0.000 description 9
- 238000007669 thermal treatment Methods 0.000 description 9
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 8
- 238000000059 patterning Methods 0.000 description 8
- YFSUTJLHUFNCNZ-UHFFFAOYSA-M 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonate Chemical compound [O-]S(=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-M 0.000 description 7
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 7
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical group C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 7
- 230000008859 change Effects 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 150000002736 metal compounds Chemical class 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 229920002120 photoresistant polymer Polymers 0.000 description 6
- 238000009832 plasma treatment Methods 0.000 description 6
- 239000004810 polytetrafluoroethylene Substances 0.000 description 6
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 238000006552 photochemical reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 4
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 238000005229 chemical vapour deposition Methods 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000001459 lithography Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 229910000449 hafnium oxide Inorganic materials 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 3
- 150000002924 oxiranes Chemical group 0.000 description 3
- 238000009877 rendering Methods 0.000 description 3
- 238000004544 sputter deposition Methods 0.000 description 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 2
- WMGVPDQNPUQRND-UHFFFAOYSA-N (2-methylphenyl)acetonitrile Chemical compound CC1=CC=CC=C1CC#N WMGVPDQNPUQRND-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- GHYCDQZHLJYSRX-UHFFFAOYSA-N 1,2-dimethoxyethane;ethyl acetate Chemical compound CCOC(C)=O.COCCOC GHYCDQZHLJYSRX-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- YAYTYCFOMPKBLT-UHFFFAOYSA-N 2-cyanoethenylideneazanide Chemical compound N#C[CH-]C#N YAYTYCFOMPKBLT-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 2
- HCGFUIQPSOCUHI-UHFFFAOYSA-N 2-propan-2-yloxyethanol Chemical compound CC(C)OCCO HCGFUIQPSOCUHI-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 2
- ZBJDBFWPAOORHG-UHFFFAOYSA-N CC1(C)OC(=O)[CH-]C(=O)O1 Chemical compound CC1(C)OC(=O)[CH-]C(=O)O1 ZBJDBFWPAOORHG-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 239000005456 alcohol based solvent Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- DGGWFOAMZZNWAV-UHFFFAOYSA-N chloro(dimethyl)silicon;tetraethyl silicate Chemical compound C[Si](C)Cl.CCO[Si](OCC)(OCC)OCC DGGWFOAMZZNWAV-UHFFFAOYSA-N 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
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- CMKBCTPCXZNQKX-UHFFFAOYSA-M cyclohexanethiolate Chemical compound [S-]C1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-M 0.000 description 1
- OHHPZPDQZMUTCA-UHFFFAOYSA-N cyclohexyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1CCCCC1 OHHPZPDQZMUTCA-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 238000007607 die coating method Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- LSSYNNOILRNWCJ-UHFFFAOYSA-N diphenyl-(2,4,6-trimethylphenyl)sulfanium Chemical compound CC1=CC(C)=CC(C)=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 LSSYNNOILRNWCJ-UHFFFAOYSA-N 0.000 description 1
- AJYOAZVTXTXTHZ-UHFFFAOYSA-M diphenyl-(2,4,6-trimethylphenyl)sulfanium;1,1,2,2,3,3-hexafluoropropane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)F.CC1=CC(C)=CC(C)=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 AJYOAZVTXTXTHZ-UHFFFAOYSA-M 0.000 description 1
- BQTNXOJCCVWLCN-UHFFFAOYSA-M diphenyl-(2,4,6-trimethylphenyl)sulfanium;trifluoromethanesulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)F.CC1=CC(C)=CC(C)=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 BQTNXOJCCVWLCN-UHFFFAOYSA-M 0.000 description 1
- RMUYKKBIADOHFL-UHFFFAOYSA-M diphenyliodanium;1,1,2,2,3,3-hexafluoropropane-1-sulfonate Chemical compound [O-]S(=O)(=O)C(F)(F)C(F)(F)C(F)F.C=1C=CC=CC=1[I+]C1=CC=CC=C1 RMUYKKBIADOHFL-UHFFFAOYSA-M 0.000 description 1
- UMIKAXKFQJWKCV-UHFFFAOYSA-M diphenyliodanium;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C=1C=CC=CC=1[I+]C1=CC=CC=C1 UMIKAXKFQJWKCV-UHFFFAOYSA-M 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000002149 energy-dispersive X-ray emission spectroscopy Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-M ethenesulfonate Chemical compound [O-]S(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-M 0.000 description 1
- IJBFRXAGQXANTD-UHFFFAOYSA-N ethenyl acetate;hafnium Chemical compound [Hf].CC(=O)OC=C IJBFRXAGQXANTD-UHFFFAOYSA-N 0.000 description 1
- NSANGDPBUXTZLU-UHFFFAOYSA-N ethenyl acetate;niobium Chemical compound [Nb].CC(=O)OC=C NSANGDPBUXTZLU-UHFFFAOYSA-N 0.000 description 1
- CEWRRSHXODUOEA-UHFFFAOYSA-N ethenyl acetate;tantalum Chemical compound [Ta].CC(=O)OC=C CEWRRSHXODUOEA-UHFFFAOYSA-N 0.000 description 1
- DCDITIFKQFNPHX-UHFFFAOYSA-N ethenyl acetate;titanium Chemical compound [Ti].CC(=O)OC=C DCDITIFKQFNPHX-UHFFFAOYSA-N 0.000 description 1
- LIIWPMGRDQVHJQ-UHFFFAOYSA-N ethenyl acetate;zirconium Chemical compound [Zr].CC(=O)OC=C LIIWPMGRDQVHJQ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- ZQTYQMYDIHMKQB-UHFFFAOYSA-N exo-norborneol Chemical compound C1CC2C(O)CC1C2 ZQTYQMYDIHMKQB-UHFFFAOYSA-N 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012949 free radical photoinitiator Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000007756 gravure coating Methods 0.000 description 1
- LCMWRQFPFWDPJB-UHFFFAOYSA-J hafnium(4+) 6-naphthalen-2-ylsulfanylbicyclo[2.2.1]heptane-2-carboxylate Chemical compound [Hf+4].[O-]C(=O)C1CC2CC(Sc3ccc4ccccc4c3)C1C2.[O-]C(=O)C1CC2CC(Sc3ccc4ccccc4c3)C1C2.[O-]C(=O)C1CC2CC(Sc3ccc4ccccc4c3)C1C2.[O-]C(=O)C1CC2CC(Sc3ccc4ccccc4c3)C1C2 LCMWRQFPFWDPJB-UHFFFAOYSA-J 0.000 description 1
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 1
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- OCUXHFVNHQTZKR-UHFFFAOYSA-M methanesulfonate;triphenylsulfanium Chemical compound CS([O-])(=O)=O.C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 OCUXHFVNHQTZKR-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical compound CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- LIODXJCUANQONM-UHFFFAOYSA-N naphthalen-1-yloxy(phenoxy)methanethiol Chemical compound O(C1=CC=CC=C1)C(S)OC1=CC=CC2=CC=CC=C12 LIODXJCUANQONM-UHFFFAOYSA-N 0.000 description 1
- SEXOVMIIVBKGGM-UHFFFAOYSA-N naphthalene-1-thiol Chemical compound C1=CC=C2C(S)=CC=CC2=C1 SEXOVMIIVBKGGM-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- MYCXXYXQXKLHFN-UHFFFAOYSA-N niobium;3-prop-2-enoyloxypropanoic acid Chemical compound [Nb].OC(=O)CCOC(=O)C=C MYCXXYXQXKLHFN-UHFFFAOYSA-N 0.000 description 1
- RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- OTGHWLKHGCENJV-UHFFFAOYSA-M oxirane-2-carboxylate Chemical compound [O-]C(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-M 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- 125000005634 peroxydicarbonate group Chemical group 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- QDSBRLMOWFYBGK-UHFFFAOYSA-N phenacyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC(=O)C1=CC=CC=C1 QDSBRLMOWFYBGK-UHFFFAOYSA-N 0.000 description 1
- CTRLRINCMYICJO-UHFFFAOYSA-N phenyl azide Chemical compound [N-]=[N+]=NC1=CC=CC=C1 CTRLRINCMYICJO-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001843 polymethylhydrosiloxane Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003214 pyranose derivatives Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000007261 regionalization Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007763 reverse roll coating Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- WOZZOSDBXABUFO-UHFFFAOYSA-N tri(butan-2-yloxy)alumane Chemical compound [Al+3].CCC(C)[O-].CCC(C)[O-].CCC(C)[O-] WOZZOSDBXABUFO-UHFFFAOYSA-N 0.000 description 1
- XDKRKTXKZQLTMH-UHFFFAOYSA-M trifluoromethanesulfonate;tris(4-chlorophenyl)sulfanium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC(Cl)=CC=C1[S+](C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 XDKRKTXKZQLTMH-UHFFFAOYSA-M 0.000 description 1
- BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- RODJBIGBBLKNHX-UHFFFAOYSA-N tris(4-chlorophenyl)sulfanium Chemical compound C1=CC(Cl)=CC=C1[S+](C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 RODJBIGBBLKNHX-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/02—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating by thermal decomposition
- C23C18/06—Coating on selected surface areas, e.g. using masks
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/14—Decomposition by irradiation, e.g. photolysis, particle radiation or by mixed irradiation sources
- C23C18/143—Radiation by light, e.g. photolysis or pyrolysis
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
- C23C18/00—Chemical coating by decomposition of either liquid compounds or solutions of the coating forming compounds, without leaving reaction products of surface material in the coating; Contact plating
- C23C18/14—Decomposition by irradiation, e.g. photolysis, particle radiation or by mixed irradiation sources
- C23C18/145—Radiation by charged particles, e.g. electron beams or ion irradiation
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/10—Apparatus or processes for manufacturing printed circuits in which conductive material is applied to the insulating support in such a manner as to form the desired conductive pattern
- H05K3/105—Apparatus or processes for manufacturing printed circuits in which conductive material is applied to the insulating support in such a manner as to form the desired conductive pattern by conversion of non-conductive material on or in the support into conductive material, e.g. by using an energy beam
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/24—Structurally defined web or sheet [e.g., overall dimension, etc.]
- Y10T428/24802—Discontinuous or differential coating, impregnation or bond [e.g., artwork, printing, retouched photograph, etc.]
Definitions
- the disclosed embodiments relate to methods of making metal-containing films, three-dimensional objects or articles via photochemical reactions.
- Sol-gel is one of the most common methods of depositing a metal oxide layer.
- the method employs spin-on coating of a sol precursor dissolved in a suitable solvent followed by heating the substrate to a high temperature to convert the precursor film into metal oxide.
- the method is not very practical in the sense that it employs quite high temperatures. High stresses related to cycles of heating and cooling involved in the process lead to defectivity. Moreover, additional processing steps are required to pattern small features into the material.
- Deposition by evaporation involves heating of metal-compound to be deposited to high temperatures. Vapors of such materials are condensed on the substrate under vacuum using a screen or shadow to form fine patterns of the material. Deposition by evaporation has limited commercial potential due to high temperatures and high vacuum requirements.
- Deposition by sputtering involves vaporization of the material to be deposited by bombarding with high-energy atomic radiation. Similar to Evaporation, the vapors of the materials can be deposited on the substrate by condensation. Utility of the process is limited due to high energy requirements and lack of precision in controlling film properties.
- Formation of fine patterns into such metal-containing layers is achieved by additional multiple steps of imaging and etching of a photosensitive film deposited on such materials.
- First a photoresist or photosensitive film is applied on the metal-containing layer and dried at an appropriate temperature to remove a majority of casting solvent followed by image-wise exposure to actinic radiation to which such photoresist material is sensitive.
- actinic radiation to which such photoresist material is sensitive.
- the exposed area of the film undergoes chemical reaction rendering it soluble in an alkaline developer. The action of developer leaves behind a fine pattern of the photoresist material.
- the exposed portion of the film undergo chemical reaction rendering it insoluble in a solvent suitable for removing unexposed area of the film, leaving behind a fine pattern of the photoresist film, which acts as an etch mask to transfer pattern into underlying metal-containing material.
- Another method of forming fine patterns involves depositing a non- photosensitive metal-containing film, into a patterned substrate.
- the non- photosensitive metal-containing film is etched back to resolve the underlying pattern.
- a photoresist-free, negative-tone method of direct patterning into metal- containing materials is described in U.S. Patent Nos. 5,534,312; 6,071 ,676 and 6,972,256.
- the metal complex used in the method is photosensitive and undergoes low-temperature reaction in the presence of light of particular wavelength rendering the exposed portion insoluble in solvent/developer.
- Disadvantages of this method include limited choices of the starting metal- containing materials which demonstrate a sharp switch in solubility behavior upon exposure requiring very high exposure doses and often treatment of harsh solvents to remove unconverted material. Such harsh solvents also attack the exposed area, destroying pattern fidelity.
- This technique involves metal compounds that show significant absorbance at the exposure wavelength. High absorbance at the film surface leads to less light penetration into the bulk of the film resulting in non-uniform photochemical reaction; hence, chemical composition of the film is quite heterogeneous across the film.
- An objective of the embodiments disclosed herein is to provide a process of forming metal-containing films, three dimensional objects or articles.
- the metal compounds of the disclosed embodiments are readily soluble in commonly used solvents for coating applications and can be applied conveniently by any known coating method.
- the metal compounds used in the disclosed embodiments are generally transparent at the exposure wavelength, leading to a more efficient photochemical reaction. Photosensitivity to such metal-containing compositions is predominantly imparted and controlled by adding a photoactive compound that acts as a photoinitiator or photoactive catalyst. Through the use of a post-treatment, the metal-containing film composition can be tuned.
- the process described herein is also useful in directly applying high dielectric constant (k) materials such as hafnium- and zirconium-based metal compositions. Thus it is possible to replace silicon dioxide (k of about 4) with a high-k material such as hafnium or zirconium oxide gates using a convenient and low-cost process described herein.
- Another objective of the embodiments disclosed herein is to provide a process of forming direct patterning of metal compounds using photosensitive compositions.
- the patterning process of the embodiments described herein utilizes well known techniques of lithography, amenable to high throughput manufacturing. Through the use of a post-treatment, the patterned metal- containing film composition can be tuned as well as the refractive index.
- the process described herein is also useful in directly patterning high dielectric constant (k) materials such as hafnium- and zirconium-based metal compositions. Thus it is possible to replace silicon dioxide (k of about 4) with a high-k material such as hafnium or zirconium oxide gates using a convenient and low-cost process described herein.
- Another objective of the disclosed embodiments is to provide a process for the production of metal-containing patterned films and three-dimensional objects or articles for protective, insulating and anti reflective properties.
- One embodiment is a process for forming a metal-containing film by applying a photosensitive metal-containing composition on a substrate, drying the photosensitive metal-containing composition, exposing the photosensitive metal-containing composition to a source of actinic radiation, and applying a post-treatment to the metal-containing composition.
- the photosensitive metal- containing composition comprises: i. a metal-containing precursor unit (MU) containing at least two reactive functional groups, and ii. a photo initiator or photoactive catalyst where MU is represented by Structure I:
- M comprises a metal with a formal valency of 0-7 and is selected from Zr, Hf 1 Ge, Ti, Pb, Gd, Sn, Zn, Ni, Ce, Nb, Eu, In, Al, Fe, Mn, Nd, Cu, Sb, Mg, Ga, Se, Cd, Ta, Co, Cr, Pt, Au, W, V, Tl, Te, Sr, Sm, La, Er, Pd, In, Ca, Ba, As and Y;
- Ligand A contains a reactive functional group capable of undergoing a combining reaction; w is 2 to 7;
- Ligands B and C are selected individually or in combination from oxygen, nitrogen, sulfur, or a halogen atom; linear, branched or cyclic alkyl, alkenyl or alkynyl group; substituted or unsubstituted aryl group; and -XR 1 where X represents an organic functional group such as oxy, thio, carboxy, thiocarboxy, s
- additional steps in the process allow for forming patterned metal-containing films, three-dimensional objects or articles.
- the process with additional steps comprise applying a photosensitive metal-containing composition on a substrate, drying the photosensitive metal-containing composition, exposing the photosensitive metal-containing composition to a source of actinic radiation through a mask or mold, developing the unexposed portion of the composition and applying a post-treatment to the metal-containing composition.
- the metal-containing film is formed by applying a photosensitive metal-containing composition on a substrate wherein the photosensitive metal-containing composition comprises: a metal-containing precursor unit (MU) containing at least two reactive functional groups, and a photoinitiator or photoactive catalyst, where MU is represented by Structure I shown above, drying the photosensitive metal-containing composition, exposing the photosensitive metal-containing composition to a source of actinic radiation and applying a post-treatment to the metal-containing composition.
- MU metal-containing precursor unit
- a further embodiment is a directly patterned metal-containing film comprising M Z E V where M comprises a metal with a formal valency of 0-7 and is selected from Zr, Hf, Ge, Ti, Pb, Gd, Sn, Zn 1 Ni 1 Ce, Nb, Eu, In, Al, Fe, Mn, Nd, Cu, Sb, Mg, Ga, Se 1 Cd, Ta, Co, Cr 1 Pt, Au, W, V, Tl, Te 1 Sr 1 Sm 1 La 1 Er 1 Pd 1 In, Ca, Ba, As and Y; E is selected individually or in combination from a group of elements such as oxygen, hydrogen, nitrogen, sulfur, carbon, silicon or fluorine; where z is about 5 to about 95% and z + v is 100%.
- M comprises a metal with a formal valency of 0-7 and is selected from Zr, Hf, Ge, Ti, Pb, Gd, Sn, Zn 1 Ni 1 Ce, Nb, Eu, In, Al, Fe, Mn,
- M comprises a metal with a formal valency of 0-7 and is selected from Zr, Hf, Ge, Ti, Pb, Gd, Sn, Zn, Ni, Ce, Nb, Eu, In, Al 1 Fe, Mn, Nd, Cu, Sb, Mg, Ga, Se, Cd 1 Ta 1 Co, Cr, Pt 1 Au 1 W 1 V, Tl, Te, Sr, Sm 1 - La, Er, Pd, In, Ca 1 Ba, As and y; E is selected individually or in combination from a group of elements such as oxygen, hydrogen, nitrogen, sulfur, carbon, silicon or fluorine; where z is about 5 to about 95% and z + v is 100% and M Z E V is formed from an irradiated post-treated photosensitive metal-containing composition wherein the photosensitive metal-containing composition comprises a combination of metal-containing precursor units (MU) containing at least two reactive functional groups
- MU metal-containing precursor units
- combining reaction refers to polymerization and/or crosslinking reactions of reactive functional groups.
- reactive functional group refers to functional groups such as epoxide, -SiH 1 a -SH group and ethylenically unsaturated functional groups such as a vinyl group, an allyl group, a (meth)acryloyl group.
- Combining reactions include reactions of ethylenically unsaturated functional groups, reactions involving ethylenically unsaturated functional groups with a - SiH group or a -SH group and reactions involving epoxides.
- the crosslinking is usually chemical crosslinking but in some cases can be physical crosslinking. Combining reactions can take place with MU and MU and with MU and various components.
- ligand refers to molecules, ions or atoms attached to the central atom of a coordination compound, a chelate or other complex.
- compatible refers to a homogeneous film which does not show precipitation or phase separation.
- (meth)acryl refers to either an acryl or a methacryl group.
- post-treatment is a treatment selected individually or in combination from thermal, chemical, or plasma which alters the chemical composition of the resulting metal-containing film.
- microdevices are devices made using microfabrication technologies.
- a process for producing metal- containing films, three-dimensional objects or articles via photochemical reactions of suitable photosensitive metal-containing compositions.
- the process comprises applying the photosensitive metal-containing compositions on to a substrate, drying the photosensitive metal-containing composition, sometimes at a temperature between 40 and 200 C C and exposing the photosensitive metal- containing composition to actinic radiation.
- the process further comprises applying a post-treatment selected individually or in combination from a thermal, chemical or plasma treatment producing metal-containing films, three- dimensional objects or articles comprising M Z E V , where M comprises a metal with a formal valency of 0-7 and is selected from Zr, Hf, Ge, Ti, Pb, Gd, Sn, Zn, Ni, Ce, Nb, Eu, In, Al, Fe, Mn, Nd, Cu, Sb, Mg, Ga, Se, Cd, Ta, Co, Cr, Pt, Au, W, V, Tl, Te, Sr, Sm, La, Er, Pd, In, Ca, Ba, As and Y; E is selected individually or in combination from a group of elements such as oxygen, hydrogen, nitrogen, sulfur, carbon, silicon or fluorine; where z is about 5 to about 95%, or about 15% to about 95%, or about 25% to about 95% and z + v is 100%.
- M comprises a metal with a formal valency of 0-7 and is
- the process further comprises producing metal-containing films, three-dimensional objects or articles producing metal-containing films, three-dimensional objects or articles with index of refraction in the range of 1.4 to 2.2 in the 400-900 nm range of light and 1.4 to 2.4 in the 150-400 nm range of light.
- the process also provides metal-containing films, three-dimensional objects or articles with dielectric constant of at least 2.
- a process for producing patterned metal- containing films, three-dimensional objects or articles via photochemical reactions of suitable photosensitive metal-containing compositions comprises applying the photosensitive metal-containing compositions on to a substrate, drying the photosensitive metal-containing composition, sometimes at a temperature between 40 and 200 0 C for about a few seconds to a few minutes, exposing the photosensitive metal-containing composition to actinic radiation through an appropriate photomask and developing away the unexposed region of the composition.
- the process further comprises applying a post-treatment selected individually or in combination from a thermal, chemical or plasma treatment producing metal-containing films, three- dimensional objects or articles comprising MzEv, where M comprises a metal with a formal valency of 0-7 and is selected from Zr, Hf, Ge, Ti, Pb, Gd, Sn, Zn, Ni, Ce 1 Nb, Eu, In, Al 1 Fe, Mn, Nd, Cu, Sb, Mg, Ga, Se, Cd, Ta, Co, Cr, Pt, Au, W, V, Tl, Te, Sr, Sm, La, Er, Pd, In, Ca, Ba, As and Y; E is selected individually or in combination from a group of elements such as oxygen, hydrogen, nitrogen, sulfur, carbon, silicon or fluorine; where z is about 5 to about 95% and z + v is 100%.
- M comprises a metal with a formal valency of 0-7 and is selected from Zr, Hf, Ge, Ti, Pb, Gd
- the process further comprises producing metal-containing films, three- dimensional objects or articles with index of refraction in the range of 1 .4 to 2.2 in the 400-900 nm range of light and 1 .4 to 2.4 in the 150-400 nm range of light.
- the process also provides metal-containing films, three-dimensional objects or articles with dielectric constant of at least 2.
- An alternative process for producing patterned metal-containing films comprises applying photosensitive metal-containing composition on to a substrate, imprinting the photosensitive metal-containing composition with a template, which could be in the form of a stamp or a dye or a mold, exposing the imprinted photosensitive metal-containing composition to actinic radiation in the form of light or heat.
- the process is referenced as 'imprint lithography 1 .
- the metal-containing composition used for imprint lithography is not necessarily photosensitive and heat can be used to induce combining reaction resulting in change of solubility behavior of the imprinted composition before and after heating.
- a thermally activated initiator or catalyst as an essential part of the metal-containing composition.
- Imprint lithography can also be performed using a photosensitive metal-containing composition, where a photoinitiator or a photoactive catalyst is used.
- the template used in the process may be transparent to the actinic light in order to expose the composition before removing the template.
- the process further comprises applying a post-treatment selected individually or in combination from a thermal, chemical or plasma treatment producing metal-containing films, three-dimensional objects or articles comprising MzEv, where M comprises a metal with a formal valency of 0-7 and is selected from Zr 1 Hf, Ge, Ti 1 Pb, Gd 1 Sn 1 Zn 1 Ni 1 Ce 1 Nb 1 Eu 1 In 1 Al 1 Fe 1 Mn 1 Nd 1 Cu 1 Sb 1 Mg 1 Ga 1 Se 1 Cd 1 Ta 1 Co 1 Cr 1 Pt 1 Au 1 W 1 V 1 Tl 1 Te 1 Sr 1 Sm 1 La 1 Er 1 Pd 1 In 1 Ca 1 Ba 1 As and Y; E is selected individually or in combination from a group of elements such as oxygen, hydrogen, nitrogen, sulfur, carbon, silicon or fluorine; where z is about 5 to about 95% and z + v is 100%.
- M comprises a metal with a formal valency of 0-7 and is selected from Zr 1 Hf, Ge, Ti 1 Pb, Gd 1
- the process further comprises for producing metal-containing films, three-dimensional objects or articles with index of refraction in the range of 1.4 to 2.2 in the 400-900 nm range of light and 1.4 to 2.4 in the 150-400 nm range of light.
- the process also provides metal-containing films, three-dimensional objects or articles with dielectric constant of at least 2.
- imprint technology is described in U.S. Pat. Nos. 5,772,905 and 6,334,960 and are incorporated herein as reference.
- the photosensitive metal-containing composition in the above embodiments comprises a metal-containing precursor unit (MU) and a photoactive catalyst or a photoinitiator.
- the photoactive catalyst or photoinitiator absorbs significant portion of the actinic light and is capable of inducing combining reactions in MU so that the composition becomes insoluble to solvent or developer employed in the subsequent step of developing away the unexposed portion of the composition.
- the MU contains at least two reactive functional groups capable of undergoing combining reactions induced by the photoactive catalyst or photoinitiator when exposed to actinic source of light.
- MU is represented by Structure I:
- M comprises a metal with formal valency of 0-7 such as Zr, Hf, Ge 1 Ti, Pb, Gd, Sn, Zn, Ni, Ce, Nb, Eu, In, Al, Fe, Mn, Nd, Cu, Sb, Mg, Ga, Se, Cd, Ta, Co, Cr, Pt, Au, W, V, Tl, Te, Sr, Sm, La, Er, Pd, In, Ca, Ba, As and Y;
- a metal with formal valency of 0-7 such as Zr, Hf, Ge 1 Ti, Pb, Gd, Sn, Zn, Ni, Ce, Nb, Eu, In, Al, Fe, Mn, Nd, Cu, Sb, Mg, Ga, Se, Cd, Ta, Co, Cr, Pt, Au, W, V, Tl, Te, Sr, Sm, La, Er, Pd, In, Ca, Ba, As and Y;
- Ligand A contains a reactive functional group capable of undergoing a combining reaction in the presence of a suitable photoinitiator or photoactive catalyst typically employed in formulating these compositions; w is 2 to 7.
- Ligand A contains an ethylenically unsaturated functional group such as a (meth)acryloyl, vinyl, allyl, styryl, or cyclic olefinic group or other reactive functional groups such as an epoxide group, a SiH group, and a SH group, which are capable of undergoing a combining reaction with other reactive functional groups of various components. This reaction generally occurs in the presence of a suitable photoinitiator or photoactive catalyst and a source of actinic radiation.
- Ligands B and C are selected individually or in combination from oxygen, nitrogen, sulfur, or a halogen atom; linear, branched or cyclic alkyl, alkenyl or alkynyl group; substituted or unsubstituted aryl group; or -XR1 where X represents an organic functional group such as oxy, thio, carboxy, thiocarboxy, sulfo, oxalate, acetoacetonate, carbanion, carbonyl, thiocarbonyl, cyano, nitro, nitrito, nitrate, nitrosyl, azide, cyanato, isocyanato, thiocyanato, isothiocyanato, amido, amine, diamine, arsine, diarsine, phosphine, and diphosphine, and R1 represents a linear, branched or cyclic alkyl or thioalkyl group, a heterocyclic group, an
- An example of an alkenyl group is ethylene.
- An example of an alkynyl group is acetylene.
- Some examples of a carbanion are 2,2-dimethyl-4,6-dioxo-1 ,3-dioxan-5-ide, dicyanomethanide, cyclopenta-2,4- dienide, and phenylethynide.
- the metal-containing precursor (MU) contains high k metals such as zirconium and hafnium.
- Ligands A, B and C are chosen to control absorbance and refractive index, control morphology, and no portion of the ligand may interfere in the reactivity of the reactive functional group of Ligand A.
- Ligands A, B and C are selected to impart solubility in a variety of organic solvents commonly used in coating formulations and to impart compatibility with other ingredients used in the preparation of the photosensitive metal-containing composition.
- the groups may also be chosen to facilitate decomposition during the thermal/plasma treatment stage of the process.
- Ligands A, B and C can also play role in controlling important functional properties such as adhesion to a variety of substrates, viscosity, mechanical and thermal properties of the film formed from the photosensitive metal-containing composition. For instance, it is important to choose functional groups that do not absorb significant portion of radiation to ensure uniform photoreaction throughout the composition. Similarly, thermal decomposition temperature of the material can be modified by choosing. appropriate functional groups. Also the mechanical properties of the film can be tailored via appropriate selection of the functional groups.
- Ligand A examples include (meth)acrylate, 2-carboxyethyl acrylate, vinyl acetate, 3-butenoate, 4-pentenoate, vinyl sulfonate, styrene sulfonate, vinylphenolate, vinyl benzoate, bicyclo[2.2.1]hept-5-ene-2-carboxylate, 2- ethoxy(meth)acrylate, 2-ethoxyvinylacetate, 3-(2,2-dimethoxypropoxy)
- Ligands B and C are oxygen atom, a sulfur atom, a nitrogen atom, a chlorine atom, methyl, ethyl, ethylene, cyclopentadiene, norb ⁇ mene, acetylene, methoxy, ethoxy, propoxy, butoxy, isopropoxy, 2- methoxyethoxy, 2-ethylhexoxy, cyclohexanolate, bicyclo[2.2.1]heptan-2-olate, phenoxy, naphthoxy, methanethiolate, ethanethiolate, propanethiolate, butanethiolate, isopropanethiolate, 2-ethylhexanethiolate, cyclohexanethiolate, bicycle[2.2.1]heptanethiolate, benzenethiolate, naphthalenethiolate, acetate, propanoate, butanoate, 2-methyl propanoate, 2-ethylhe
- metal-containing precursor unit is zirconium (meth)acrylate, zirconyl di(meth)acrylate, zirconium butoxide (meth)acrylate, zirconium carboxyethyl acrylate, zirconium vinyl acetate, zirconyl di(vinyl acetate), zirconium 3-oxatricyclo[3.2.1.0 2l4 ]octane-6-carboxylate, zirconium 2-bromo-5-oxo-4-oxatricyclo[4.2.1.0 3 7 ]nonane-9-carboxylate
- ligands and metal-containing precursor units are provided in co-pending U.S. Patent Application No. 11/792,738 and U.S. Patent Application No. 11/792,739.
- the photoactive catalyst or photoinitiator used in the composition is a compound that absorbs light at the wavelength of exposure and is capable of catalyzing combining reactions of the MU and/or other various components, when composition or a portion of composition is exposed to light.
- An example of a free-radical photoinitiator is 1-hydroxy-cyclohexyl-phenyl-ketone, (Irgacure 184) from Ciba Specialty Chemicals.
- An example of a photoactive catalyst is a photoacid generator such as triphenyl sulfonium triflate from Aldrich Catalog No. 526940.
- photoinitiators include but are not limited to 2- hydroxy-2-methyl-1 -phenylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone (Irgacure 184 from Ciba Specialty Chemical), a blend of 1- hydroxycyclohexylphenylketone and benzophenone (Irgacure 500 from Ciba Specialty Chemical), 2,4,4-trimethylpentyl phosphine oxide (Irgacure 1800, 1850, and 1700 from Ciba Specialty Chemical), 2,2-dimethoxyl-2-acetophenone (Irgacure 651 from Ciba Specialty Chemical), bis(2,4,6-trimethyl benzoyl)phenyl- phosphine oxide (Irgacure 819 from Ciba Specialty Chemical), 2-methyl-1-[4- (methylthio)phenyl]-2-morphorinopropane-1-on (Irgacure 907),
- nonionic-type photoactive catalysts are phenacyl p- methylbenzenesulfonate, benzoin p-toluenesulfonate, ⁇ -(p-toluene- sulfonyloxy)methylbenzoin, 3-(p-toluenesulfonyloxy)-2-hydroxy-2-phenyl-1- phenylpropyl ether, N-(p-dodecylbenzenesulfonyloxy)-1 ,8-naphthalimide and N- (phenyl-sulfonyloxy)-1 ,8-napthalimide, (2Z)-(2-methylphenyl)[(2Z)-2- ⁇ [(propylsulfonyl)oxy]imino ⁇ thiophen-3(2H)-ylidene]acetonitrile, (2Z)-[(2Z)-2-[(2Z)-2-
- ionic-type photoactive catalysts are triphenyl sulfonium methanesulfonate, triphenyl sulfonium trifluoromethanesulfonate, triphenyl sulfonium hexafluoropropanesulfonate, triphenyl sulfonium nonafluorobutanesulfonate, triphenyl sulfonium perfluorooctanesulfonate, triphenyl sulfonium phenyl sulfonate, triphenyl sulfonium 4-methyl phenyl sulfonate, triphenyl sulfonium 4-methoxyphenyl sulfonate, triphenyl sulfonium 4- chlorophenyl sulfonate, triphenyl sulfonium camphorsulfonate, 4-methylphenyl- diphenyl sulfonium trifluorome
- catalysts or initiators useful in inducing a combining reaction the presence of heat include but are not limited to organic peroxides such as benzoyl peroxide, diacylperoxides, peroxydicarbonates, alkylperesters, alkyl peroxides, perketals, ketoneperoxides, and alkylhydroperoxides; azo compounds such as azobisisobutyronitrile and 1 ,1 '- azobis(cyclohexanecarbonitrile); and thermal acid generators such as cyclohexyltosylate and K-Cure 1040 from King Industries.
- the catalyst or initiator is typically employed in the amounts of about
- the amount of catalyst or initiator is based on the combined weights of MU and/or other various components.
- the photosensitive metal-containing composition may further comprise treated or untreated metal-containing nanoparticles.
- the metal entity of the nanoparticles and the metal-containing precursor unit (MU) may be different and the ratio of metal atoms to organic atoms is from about 5:1 to about 10:1.
- the nanoparticles suitable for this application are preferably less than 20 ⁇ m in diameter and are compatible with the other components of the photosensitive composition. Examples of such nanoparticles are found in U.S. Patent Nos. 6,291 ,070 and 6,844,950.
- metal-containing nanoparticles are surface treated or untreated silica, alumina, titania, zirconia, hafnia, CdSe, CdS, CdTe, CuO, zinc oxide, lanthanum oxide, niobium oxide, tungsten oxide, strontium oxide, calcium titanium oxide, sodium titanate, and potassium niobate.
- the photosensitive metal-containing composition may further comprise a prepolymer unit (PU) which contains at least two reactive functional groups.
- PU prepolymer unit refers to a monomer unit or an oligomer where oligomer refers to combination of monomer units joined together.
- the prepolymer may contain many monomer units and is capable of further reactions to be incorporated in the final material.
- monomer units/oligomers are based on one or more of the following types: acrylate, ester, vinyl alcohol, urethane, urea, imide, amide, carbaxazole, carbonate, pyranose, siloxane, urea-formaldehyde and melamine-formaldehyde.
- the PU contains at least two terminal and/or pendant reactive functional groups. These can participate in combining reactions with metal-containing precursor units (MU).
- MU metal-containing precursor units
- terminal and pendant groups are a vinyl group, an allyl group, a (meth)acryloyl group, an epoxy group, a SiH group and a -SH group.
- An important criterion in the selection of the MU and the PU for the metal containing composition of this embodiment is that they are compatible with each other.
- Specific examples of prepolymer unit (PU) include urethane acrylate oligomer.
- urethane acrylate oligomer refers to a class of compounds that contain urethane linkages and have (meth)acrylate functional groups such as urethane multi(meth)acrylate, multiurethane (meth)acrylate, and multiurethane multi(meth)acrylate.
- prepolymer unit (PU) examples include 1 ,6-hexanediol di(meth)acrylate, tetraethyleneglycol di(meth)acrylate, divinylbenzene, ethoxylated bisphenol-A- di(meth)acrylate, diethylene glycol bis(allyl carbonate), trimethylolpropane tri(meth)acrylate, ditrimethylolpropane tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta-/hexa-(meth)acrylate, isocyanurate tri(meth)acrylate, bis(2-hydroxyethyl)-isocyanurate di(meth)acrylate, 1 ,3-butanediol tri(meth)acrylate, 1 ,4-butanediol tri(meth)acryl
- siloxane prepolymer units include vinyl-, epoxide- or (meth)acryl-terminated polyhedyrl oligomeric silsesquioxanes (POSS) (Hybrid Plastics codes OL1160, EP0409, MA0735 and MA0736), vinyl-terminated polydimethylsiloxanes (CAS 68083-19-2), vinyl terminated diphenylsiloxane-dimethylsiloxane copolymer (CAS 68951-96-2), vinyl terminated polyphenylmethylsiloxane (CAS 225927-21-9), vinyl terminated diethylsiloxane-dimethylsiloxane copolymer (Gelest Code EDV- 2025), vinylmethylsiloxane-dimethylsiloxane copolymers, trimethylsiloxy terminated (CAS 67762-94-1 ), vinylmethylsiloxane-dimethylsiloxane copolymers, vinyl terminated (CAS 6776
- Vinyl T-structured polymers (Gelest Code VTT- 106 and MTV-124), vinylmethylsiloxane terpolymers (CAS 597543-32-3), vinylmethoxysiloxane homopolymer (CAS 131298-48-1 ), vinylethoxysiloxane homopolymer (CAS 29434-25-1 ), vinyl-propylethoxysiloxane copolymer (Gelest Code VPE-005), hydride terminated poly-dimethyl siloxanes (CAS 70900-21-9), methylhydrosiloxane-dimethylsiloxane copolymers, trimethylsiloxy terminated (CAS 68037-59-2), methylhydrosiloxane-dimethylsiloxane copolymers, hydride terminated (CAS 69013-23-6), polymethylhydrosiloxanes, trimethylsiloxy terminated (CAS 63148-57-2), polyethylhydrosiloxane,
- the prepolymer often has an average molecular weight between 70 and 10 7 Daltons. A more preferred upper limit of molecular weight is 10 6 Daltons. The most preferred upper limit of molecular weight is 10 5 Daltons.
- the photosensitive metal-containing composition may further comprise a suitable solvent.
- suitable solvent The choice of solvent for the formulation and the concentration thereof depends principally on the type of functionalities incorporated in the metal-containing precursor unit (MU) and/or other various components along with the photoactive catalyst or photoinitiator and the coating method.
- the solvent should be inert, should dissolve or uniformly disperse all the components in the composition, should not undergo any chemical reaction with the components, and should be removable on drying after coating.
- Suitable solvents for the composition may include non-aqueous solvents such as ketones, ethers, esters and alcohols.
- ketones, ethers, and esters include 2-butanone, 3- methyl-2-butanone, 2-heptanone, cyclopentanone, cyclohexanone, 2-methoxy-1- propylene acetate, 2-methoxyethanol, 2-ethoxyethanol, 2-ethoxyethyl acetate, I- methoxy-2-propyl acetate, 1 ,2-dimethoxy ethane ethyl acetate, cellosolve acetate, methyl lactate, ethyl lactate, n-butyl acetate, methyl pyruvate, ethyl pyruvate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, N-methyl-2-pyrrolidone, 1 ,4-dioxane, ethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol dio
- the photosensitive metal-containing composition of the process may further comprise conventional additives, such as dyes, surface active agents, adhesion promoters, viscosity modifiers, buffers, sensitizers, stabilizers, anti- oxidants, colorants, dyes, pigments and surfactants.
- a dye may be used to improve the sensitivity of the coating to actinic light.
- the photosensitive metal-containing composition may further comprise organic monomer containing one reactive functional group or a polymer.
- organic monomer containing one reactive functional group or a polymer For instance, acrylate monomer or vinyl ether may be used to improve the physical properties of the final film such as viscosity.
- the acrylate monomer or vinyl ether is incorporated into the film or article by combining reactions with MU and/or other various components.
- the process described in the above embodiments comprises formulating by mixing appropriate proportions of different components used in the photosensitive metal-containing composition until a homogeneous solution is obtained.
- the components are mixed in a clean container which can block UV light.
- the solutions are filtered through appropriate filter media such as PTFE, nylon, polypropylene, surface treated polyethylene or polypropylene, etc.
- the nominal pore size of the filter media is ⁇ 5 ⁇ m.
- the photosensitive metal-containing composition is uniformly coated onto a suitable substrate, such as metal, plastic, wood, paper, glass, ceramic and semiconducting materials including silicon, gallium arsenide, etc.
- a suitable substrate such as metal, plastic, wood, paper, glass, ceramic and semiconducting materials including silicon, gallium arsenide, etc.
- the substrate may be planar, patterned or 3-dimensional.
- the coatings may be applied by dipping (or dip coating), knife coating, lamination, brushing, spraying, spin- coating, die coating, micro-gravure coating, cast-transfer or reverse-roll coating.
- the composition may also be applied by drop-dispense techniques where only a small amount of the composition is applied in a specified area.
- the process of the above embodiments further comprises a drying step is employed to drive off any organic solvent or other volatile materials to form a uniform defect-free coating.
- a drying step is heating at a temperature is in the range of about 40 °C to 200 °C for about a few seconds to a few minutes.
- the process of the above embodiments further comprises exposing the photosensitive metal-containing composition to actinic radiation source.
- actinic radiation is light (broadband or specific wavelength from about 0.01 nm to about 600 nm).
- actinic light sources include high pressure mercury lamp, excimer lasers, electron beam, and x-ray sources.
- the process described in the second embodiment comprises exposing the photosensitive metal-containing composition to actinic radiation through an appropriate photomask.
- a photomask is an opaque substrate with transparent patterns such as holes, lines, and spaces that allow light to shine through.
- An example of a photomask is a transparent fused silica, calcium fluoride or magnesium fluoride blank covered with a chrome pattern.
- the next step in the process described in the second embodiment comprises developing of the unexposed portion of the composition by applying a suitable solvent.
- the unexposed regions of the composition are soluble in solvent and dissolve away, leaving a pattern.
- the solvent may be applied to the substrate by spraying, dipping or puddling.
- the total contact time with the solvent can vary from a few seconds to a few minutes. The time needed to dissolve unexposed regions of the composition would determine the suitable solvent.
- Suitable solvents for developing the unexposed regions of the composition may be selected invidually or in combination from non-aqueous solvents such as ketones, ethers, esters and alcohols as well as aqueous alkaline and aqueous acidic solutions.
- ketones, ethers, and esters examples include 2-butanone, 3-methyl-2- butanone, 2-heptanone, cyclopentanone, cyclohexanone, 2-methoxy-1 -propylene acetate, 2-methoxyethanol, 2-ethoxyethanol, 2-ethoxyethyl acetate, l-methoxy-2- propyl acetate, 1 ,2-dimethoxy ethane ethyl acetate, cellosolve acetate, methyl lactate, ethyl lactate, ⁇ -butyl acetate, methyl pyruvate, ethyl pyruvate, methyl 3- methoxypropionate, ethyl 3-methoxypropionate, N-methyl-2-pyrrolidone, 1 ,4- dioxane, ethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol di
- any residual solvent and other volatile components may be removed by applying a drying step.
- a drying step include spin-drying or at temperature in the range of about 40 °C to 200 °C for about a few seconds to a few minutes.
- the next step in the process described in the above embodiments further comprises applying a post-treatment selected individually or in combination from a thermal, chemical or plasma treatment.
- the resulting metal-containing film, article or three-dimensional object comprises M Z E V) where M is metal as described in Structure I; E is selected individually or in combination from a group of elements such as oxygen, hydrogen, nitrogen, sulfur, carbon, silicon or fluorine; where z is about 5 to about 95% and z + v is 100%.
- the post-treatment results in a change of refractive index for the metal-containing film, article or three-dimensional object of at least about ⁇ 0.1 , or a refractive index change of at least about ⁇ 0.2 or refractive index change of at least about ⁇ 0.25.
- the process including a post-treatment produces metal- containing films, articles or three-dimensional objects with index of refraction in the range of 1.4 to 2.2 in the 400-900 nm range of light and 1.4 to 2.4 in the 150- 400 nm range of light.
- the process also provides metal-containing films, three- dimensional objects or articles with dielectric constant of at least 2.
- Non-limiting examples of thermal treatment involve elevated temperatures
- metal-containing compositions typically greater than 200 0 C
- a suitable atmosphere such as air, oxygen, nitrogen, etc.
- One non-limiting example of a chemical treatment is employing ozone treatment.
- One non-limiting example of a plasma treatment is employing oxygen plasma.
- the embodiments described herein also include a metal-containing film, three-dimensional object or article formed by the photosensitive metal-containing compositions and the processes described above.
- the disclosed embodiments also include a coated, a laminated, or a molded article formed by the photosensitive metal-containing compositions and the processes described above.
- the disclosed embodiments further include a microdevice formed by the photosensitive metal-containing compositions and the processes described above.
- the metal-containing precursor unit (MU) for each example was prepared as described in copending U.S. Patent Application No. 11/792,738 and U.S. Patent Application No. 11/792,739, the contents of which are incorporated herein by reference in their entirety.
- sample Preparation A solution of zirconium n-butoxide (80 wt% in n-butanol from Sigma-Aldrich Corp.) was diluted to 25 wt% with n-butanol. The resulting mixture was homogeneous after stirring. The homogeneous and clear solution was filtered through a 1.0 ⁇ m PTFE syringe filter. The solution was spin-coated onto a 1" silicon wafers at wet coating thickness of about 1.2 ⁇ m and dried for 60 seconds at 130 0 C on a hotplate.
- the coating became opaque white powder that easily flaked off the substrate.
- the coating quality demonstrates that zirconium n-butoxide would not be stable for the subsequent steps of the process and is therefore an unsuitable material for this process.
- Each solution was prepared by dissolving the metal- containing precursor unit (MU) in the solvent or solvent combination as listed in Table 1 (15 wt% in solution).
- the examples with photoinitiator contain 8.8 wt% (based on weight of MU) of 1-hydroxy-cyclohexyl-phenyl-ketone, lrgacure 184 from Ciba Specialty Chemicals and 1.2 wt% (based on weight of MU) of bis(2,4,6-trimethylbenzoyl)-phenylphosphineoxide, lrgacure 819 from Ciba Specialty Chemicals.
- the resulting mixture was homogeneous after stirring.
- the homogeneous solution was filtered through a 1.0 ⁇ m PTFE syringe filter.
- Solubility Test The solutions prepared above were individually tested by coating onto a Luminor T PET film from Toray (75 ⁇ m thick) with a wire-wound coater (3 mil diameter), Catalog No. AR-4103 from BYK Gardner to a wet coating thickness of about 5 ⁇ m and drying for 60 seconds at 80 0 C in an oven. Each dried composition was exposed by a Blak-ray. UV lamp Model 100 AP for 15 minutes. The solubility of the resulting composition was determined by mechanically rubbing a cotton swab soaked in acetone. The data are shown in
- the following examples demonstrate formation of a metal-containing film through the process of applying a photosensitive metal-containing composition on steel or tungsten, drying the photosensitive metal-containing composition, exposing the photosensitive metal-containing composition to a source of UV light and applying a thermal treatment to produce a metal-containing film.
- a solution was prepared by dissolving hafnium carboxyethyl acrylate (25 wt%) in 2-butanone/n-butanol (75:25). The the solution was added 10 wt% of 1-hydroxy-cyclohexyl-phenyl-ketone, lrgacure 184 from Ciba Specialty Chemicals. The resulting mixture was homogeneous after stirring. The homogeneous and clear solution was filtered through a 1.0 ⁇ m PTFE syringe filter. Each solution was dip-coated onto metal coupons that are 0.5" x 1" and dried for 120 seconds at 120 0 C on a hotplate.
- Each coupon was exposed by a Blak-ray UV lamp Model 100 AP for 15 minutes. Each coupon was thermally treated at 250 0 C for 30 minutes in an oven then heated to a higher temperature for 60 minutes.
- the type of metal coupon used, the final temperature of the thermal treatment and metal content as measured by Energy Dispersive X-ray Spectroscopy are listed in Table 2.
- the results of Table 2 indicate that the process of applying a photosensitive metal-containing composition on steel or tungsten, drying the photosensitive metal-containing composition, exposing the photosensitive metal-containing composition to a source of UV light and applying a thermal treatment forms a metal-containing film with a hafnium content of 77-84%.
- M Z E V where M is hafnium, E is a combination of oxygen and carbon, z is 77-84% and z + v is 100%.
- Examples 17-18 The following examples demonstrate producing metal-containing films with index of refraction in the range of 1.4 to 2.2 in the 400-900 nm range of through the process of applying a photosensitive metal-containing composition on silicon, drying the photosensitive metal-containing composition, exposing the photosensitive metal-containing composition to a source of UV light and applying a thermal treatment.
- Each solution was prepared by dissolving the metal- containing precursor unit (MU) in the solvent or solvent combination as listed in Table 3 (25 wt% in solution). To each solution was added 10 wt% (based on weight of MU) of 1-hydroxy-cyclohexyl-phenyl-ketone, lrgacure 184 from Ciba Specialty Chemicals. The resulting mixture was homogeneous after stirring. The homogeneous and clear solution was filtered through a 0.2 ⁇ m PTFE syringe filter. Each solution was spin-coated onto four 1" silicon wafers at wet composition thickness of about 2.6 ⁇ m and dried for 60 seconds at 100 0 C on a hotplate.
- MU metal- containing precursor unit
- Each wafer was exposed by a Blak-ray UV lamp Model 100 AP for 15 minutes. For each solution, one of the exposed wafers was heated to 300 0 C for one hour in an oven, another exposed wafer was heated to 400 0 C for one hour in an oven, a third exposed wafer was heated to 500 0 C for one hour in an oven, and a fourth exposed wafer was heated to 600°C for one hour in an oven.
- the refractive index and film thickness of each wafer were measured on a Gaertner Ellipsometer at 633 nm and 830 nm are listed in Table 3. Table 3
- the following examples demonstrate the capability of the photosensitive metal- containing composition to form patterns through process of applying a photosensitive metal-containing composition on silicon, drying the photosensitive metal-containing composition, exposing the photosensitive metal-containing composition to UV light through a mask, developing the unexposed portions of the composition with solvent and applying a thermal treatment successfully produces metal-containing three-dimensional objects.
- Each solution was prepared by dissolving the metal- containing precursor unit (MU) in the solvent or solvent combination as listed in Table 4 (15 wt% in solution). To each solution was added 8.8 wt% (based on weight of MU) of 1-hydroxy-cyclohexyl-phenyl-ketone, lrgacure 184 from Ciba Specialty Chemicals and 1.2 wt% (based on weight of MU) of bis(2,4,6- trimethylbenzoyl)-phenylphosphineoxide, lrgacure 819 from Ciba Specialty Chemicals. The resulting mixture was homogeneous after stirring.
- MU metal- containing precursor unit
- the homogeneous and clear solution was filtered through a 0.2 ⁇ m PTFE syringe filter.
- the solution was spin-coated onto a 2" silicon wafer a wet thickness of about 5 ⁇ m and dried for 60 seconds at 100 0 C on a hotplate.
- This dried composition was exposed through a binary photomask with feature sizes 40 to 5 ⁇ m by a Blak-ray UV lamp Model 100 AP for 15 minutes.
- the unexposed regions of the composition were developed away by rinsing with acetone for 60 seconds.
- the patterned wafer was heated to 200 0 C for 5 minutes.
- the patterned wafer was examined under a microscope set from 500 to 10,000X magnification.
- Examples 19 to 23 show that the process of applying a photosensitive metal-containing composition on silicon, drying the photosensitive metal- containing composition, exposing the photosensitive metal-containing composition to UV light through a mask and developing the unexposed portions of the composition with solvent successfully produces metal-containing three- dimensional objects. Examples 19 and 20 were post-treated at 400 0 C for 60 minutes.
- the patterned features were retained as seen under microscope showing that the process of applying a photosensitive metal-containing composition on silicon, drying the photosensitive metal-containing composition, exposing the photosensitive metal- containing composition to UV light through a mask and developing the unexposed portions of the composition with solvent and applying a thermal treatment successfully produces metal-containing three-dimensional objects.
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US12/737,694 US8802346B2 (en) | 2008-08-07 | 2009-06-27 | Metal compositions and methods of making same |
TW098126808A TWI547528B (en) | 2008-08-07 | 2009-08-10 | Metal compositions and methods of making same |
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US12/737,694 A-371-Of-International US8802346B2 (en) | 2008-08-07 | 2009-06-27 | Metal compositions and methods of making same |
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Also Published As
Publication number | Publication date |
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EP2326744B1 (en) | 2022-06-01 |
EP2326744A4 (en) | 2017-02-08 |
TW201012880A (en) | 2010-04-01 |
JP2011530652A (en) | 2011-12-22 |
US20110184139A1 (en) | 2011-07-28 |
TWI547528B (en) | 2016-09-01 |
US8802346B2 (en) | 2014-08-12 |
JP6004649B2 (en) | 2016-10-12 |
EP2326744A1 (en) | 2011-06-01 |
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