TW200405128A

TW200405128A - Novel sulfonyldiazomethanes, photoacid generators, resist compositions, and patterning process

Novel sulfonyldiazomethanes, photoacid generators, resist compositions, and patterning process Download PDF

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Publication number: TW200405128A
Authority: TW; Taiwan
Prior art keywords: acid; group; carbon atoms; bis; photoresist material
Prior art date: 2002-05-01

Application number

TW092110047A

Other languages

English (en)

Chinese (zh)

Other versions

TWI305869B (https=

Inventor

Katsuhiro Kobayashi

Koji Hasegawa

Toshihiko Fujii

Kazunori Maeda

Youichi Ohsawa

Original Assignee

Shinetsu Chemical Co

Priority date

2002-05-01

Filing date

2003-04-29

Publication date

2004-04-01

2003-04-29 Application filed by Shinetsu Chemical Co filed Critical Shinetsu Chemical Co

2004-04-01 Publication of TW200405128A publication Critical patent/TW200405128A/zh

2009-02-01 Application granted granted Critical

2009-02-01 Publication of TWI305869B publication Critical patent/TWI305869B/zh

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CSYSRRCOBYEGPI-UHFFFAOYSA-N diazo(sulfonyl)methane Chemical class [N-]=[N+]=C=S(=O)=O CSYSRRCOBYEGPI-UHFFFAOYSA-N 0.000 title claims abstract description 30
238000000034 method Methods 0.000 title claims description 23
239000000203 mixture Substances 0.000 title abstract description 16
238000000059 patterning Methods 0.000 title 1
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 92
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 51
238000000576 coating method Methods 0.000 claims abstract description 28
125000006165 cyclic alkyl group Chemical group 0.000 claims abstract description 28
239000011248 coating agent Substances 0.000 claims abstract description 27
125000003118 aryl group Chemical group 0.000 claims abstract description 12
125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
239000001257 hydrogen Substances 0.000 claims abstract description 3
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
-1 sulfofluorenyldiazomethane compound Chemical class 0.000 claims description 426
229920002120 photoresistant polymer Polymers 0.000 claims description 150
229920000642 polymer Polymers 0.000 claims description 112
239000002253 acid Substances 0.000 claims description 110
239000000463 material Substances 0.000 claims description 110
150000001875 compounds Chemical class 0.000 claims description 80
239000011347 resin Substances 0.000 claims description 52
229920005989 resin Polymers 0.000 claims description 52
125000001424 substituent group Chemical group 0.000 claims description 48
125000000217 alkyl group Chemical group 0.000 claims description 41
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
239000002904 solvent Substances 0.000 claims description 40
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 39
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 29
150000007514 bases Chemical class 0.000 claims description 22
238000003384 imaging method Methods 0.000 claims description 21
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 20
125000004122 cyclic group Chemical group 0.000 claims description 15
238000006467 substitution reaction Methods 0.000 claims description 14
150000007524 organic acids Chemical class 0.000 claims description 13
239000000758 substrate Substances 0.000 claims description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 10
150000005215 alkyl ethers Chemical class 0.000 claims description 10
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230000005855 radiation Effects 0.000 claims description 10
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125000005842 heteroatom Chemical group 0.000 claims description 9
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 7
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000004665 trialkylsilyl group Chemical group 0.000 claims description 7
125000005243 carbonyl alkyl group Chemical group 0.000 claims description 6
238000010438 heat treatment Methods 0.000 claims description 6
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125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
150000002469 indenes Chemical class 0.000 claims description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
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238000011161 development Methods 0.000 abstract description 28
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239000012535 impurity Substances 0.000 description 23
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NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 10
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102100026066 Phosphoprotein associated with glycosphingolipid-enriched microdomains 1 Human genes 0.000 description 9
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JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 7
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