JP2013140352A - 光酸発生剤およびこれを含むフォトレジスト - Google Patents
光酸発生剤およびこれを含むフォトレジスト Download PDFInfo
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- JP2013140352A JP2013140352A JP2012273444A JP2012273444A JP2013140352A JP 2013140352 A JP2013140352 A JP 2013140352A JP 2012273444 A JP2012273444 A JP 2012273444A JP 2012273444 A JP2012273444 A JP 2012273444A JP 2013140352 A JP2013140352 A JP 2013140352A
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- photoacid generator
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- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 5
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- 239000000758 substrate Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000002148 esters Chemical class 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 150000001408 amides Chemical class 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 12
- -1 ketal Chemical compound 0.000 claims description 12
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- 125000003367 polycyclic group Chemical group 0.000 claims description 9
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- 125000002950 monocyclic group Chemical group 0.000 claims description 8
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
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- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- OOIBFPKQHULHSQ-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)C(=C)C)C3 OOIBFPKQHULHSQ-UHFFFAOYSA-N 0.000 description 3
- FSQLAHNTXMNMPI-UHFFFAOYSA-N 5-bromo-4,4,5,5-tetrafluoropentanoyl chloride Chemical compound FC(F)(Br)C(F)(F)CCC(Cl)=O FSQLAHNTXMNMPI-UHFFFAOYSA-N 0.000 description 3
- 102100024003 Arf-GAP with SH3 domain, ANK repeat and PH domain-containing protein 1 Human genes 0.000 description 3
- 102100026291 Arf-GAP with SH3 domain, ANK repeat and PH domain-containing protein 2 Human genes 0.000 description 3
- 101710112065 Arf-GAP with SH3 domain, ANK repeat and PH domain-containing protein 2 Proteins 0.000 description 3
- 101100380306 Homo sapiens ASAP1 gene Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 101150003633 PAG2 gene Proteins 0.000 description 3
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- 239000000654 additive Substances 0.000 description 3
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- 230000002209 hydrophobic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000000671 immersion lithography Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- DLWBKIRSAHHFCY-UHFFFAOYSA-M lithium;2,2-difluoro-2-sulfoacetate Chemical compound [Li+].OS(=O)(=O)C(F)(F)C([O-])=O DLWBKIRSAHHFCY-UHFFFAOYSA-M 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GQJCAQADCPTHKN-UHFFFAOYSA-N methyl 2,2-difluoro-2-fluorosulfonylacetate Chemical compound COC(=O)C(F)(F)S(F)(=O)=O GQJCAQADCPTHKN-UHFFFAOYSA-N 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- CYVOZVLWADJEEB-UHFFFAOYSA-N n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC(CO)(CO)CO CYVOZVLWADJEEB-UHFFFAOYSA-N 0.000 description 1
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- MZLGASXMSKOWSE-UHFFFAOYSA-N tantalum nitride Chemical compound [Ta]#N MZLGASXMSKOWSE-UHFFFAOYSA-N 0.000 description 1
- LLFNZCQAFAVOLK-UHFFFAOYSA-N tert-butyl 4-oxo-1h-pyridine-2-carboxylate Chemical compound CC(C)(C)OC(=O)C1=CC(O)=CC=N1 LLFNZCQAFAVOLK-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- SXPSZIHEWFTLEQ-UHFFFAOYSA-N tröger's base Chemical compound C12=CC=C(C)C=C2CN2C3=CC=C(C)C=C3CN1C2 SXPSZIHEWFTLEQ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/18—Bridged systems
-
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
-
- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
または、前記のモノマーの少なくとも1種を含む組み合わせが挙げられうる。
または、前記のモノマーの少なくとも1種を含む組み合わせが挙げられうる。
または、前記のモノマーの少なくとも1種を含む組み合わせが挙げられうる。
または、前記のものと少なくとも1種の追加のモノマーとを含む組み合わせが挙げられうる。
Claims (11)
- 式(I):
L1は連結基であって、当該連結基はO、S、N、Fもしくは前記のものの少なくとも1つを含む組み合わせを含むヘテロ原子を含み;
G+は式(II):
XはSまたはIであり、
各R0は独立してC1−30アルキル基、多環式もしくは単環式C3−30環式アルキル基、多環式もしくは単環式C4−30アリール基、または前記のものの少なくとも1つを含む組み合わせであるが、各R0がC6単環式アリール基である場合には、少なくとも1つのR0は置換されており、XがIである場合にはxは2であり、XがSである場合にはxは3である)のオニウム塩であり、並びに
pは0もしくは1であり、qは1〜10の整数である]
の光酸発生剤。 - L1が、エーテル、エステル、アミン、アミド、ケトン、アセタール、ケタール、スルフィド、ジスルフィド、チオカルボニル、スルホナート、スルホンアミドまたは前記の基の少なくとも1つを含む組み合わせを含むC1−30連結基である、請求項1に記載の光酸発生剤。
- L1が線状もしくは分岐、およびフッ素化もしくは非フッ素化であり、かつC1−10アルキレン、C1−10アルキレンオキシ、C1−10エステル、C1−10アミド、C1−10スルホナート、C1−10スルホンアミド、または前記のものの少なくとも1つを含む組み合わせである、請求項1に記載の光酸発生剤。
- 式(III):
- G+が式(X)〜(XV)
R3、R4、R5、R6、R7、R8、R9、R10、R11およびR12はそれぞれ独立してH、ハロゲン、C1−10アルキル、C1−10アルコキシ、C6−10アリール、チオフェノキシ、チオアルコキシ、アルコキシカルボニルまたは前記のものの少なくとも1つを含む組み合わせであり、R3、R4、R5、R6、R7、R8、R9、R10、R11およびR12はそれぞれ、場合によっては、酸不安定基、塩基不安定基または塩基可溶性基を含み、
mは1〜10の整数であり、並びにnは1または2である]
のスルホニウム塩である、請求項1〜7のいずれか1項に記載の光酸発生剤。 - 請求項1〜9のいずれかの光酸発生剤、および酸脱保護性コポリマーを含むフォトレジスト。
- (a)基体表面上にパターン形成される1以上の層を有する基体;および
(b)前記パターン形成される1以上の層上の請求項10のフォトレジストの層;
を含むコーティングされた膜。
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US201161582341P | 2011-12-31 | 2011-12-31 | |
US61/582,341 | 2011-12-31 |
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JP (1) | JP6039396B2 (ja) |
KR (1) | KR101409787B1 (ja) |
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US9551928B2 (en) * | 2009-04-06 | 2017-01-24 | Fujifilm Corporation | Actinic-ray- or radiation-sensitive resin composition and method of forming pattern therewith |
US9671689B2 (en) | 2009-12-10 | 2017-06-06 | Rohm And Haas Electronic Materials Llc | Cholate photoacid generators and photoresists comprising same |
JP2013079232A (ja) | 2011-09-30 | 2013-05-02 | Rohm & Haas Electronic Materials Llc | 光酸発生剤およびこれを含むフォトレジスト |
US11834419B2 (en) * | 2018-10-11 | 2023-12-05 | Lg Chem, Ltd. | Compound, photoresist composition comprising same, photoresist pattern comprising same, and method for manufacturing photoresist pattern |
US20210242102A1 (en) * | 2020-02-04 | 2021-08-05 | Intel Corporation | Underfill material for integrated circuit (ic) package |
CN114380722B (zh) * | 2021-12-30 | 2023-06-30 | 宁波南大光电材料有限公司 | 一种磺酰氟烷烃酯的快速水解方法 |
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JP2011231104A (ja) * | 2010-03-31 | 2011-11-17 | Rohm & Haas Electronic Materials Llc | 光酸発生剤およびこれを含むフォトレジスト |
US20130084525A1 (en) * | 2011-09-30 | 2013-04-04 | Rohm And Haas Electronic Materials Llc | Photoacid generator and photoresist comprising same |
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JP5124805B2 (ja) * | 2006-06-27 | 2013-01-23 | 信越化学工業株式会社 | 光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 |
JP5124806B2 (ja) * | 2006-06-27 | 2013-01-23 | 信越化学工業株式会社 | 光酸発生剤並びにこれを用いたレジスト材料及びパターン形成方法 |
JP4911469B2 (ja) * | 2007-09-28 | 2012-04-04 | 富士フイルム株式会社 | レジスト組成物及びこれを用いたパターン形成方法 |
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- 2012-12-14 JP JP2012273444A patent/JP6039396B2/ja active Active
- 2012-12-26 TW TW101150051A patent/TWI462897B/zh active
- 2012-12-28 CN CN201210586171.8A patent/CN103186046B/zh active Active
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Patent Citations (4)
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JP2010237695A (ja) * | 2006-12-25 | 2010-10-21 | Fujifilm Corp | パターン形成方法、該パターン形成方法に用いられる多重現像用ポジ型レジスト組成物、該パターン形成方法に用いられるネガ現像用現像液及び該パターン形成方法に用いられるネガ現像用リンス液 |
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JP2011231104A (ja) * | 2010-03-31 | 2011-11-17 | Rohm & Haas Electronic Materials Llc | 光酸発生剤およびこれを含むフォトレジスト |
US20130084525A1 (en) * | 2011-09-30 | 2013-04-04 | Rohm And Haas Electronic Materials Llc | Photoacid generator and photoresist comprising same |
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KR20130079276A (ko) | 2013-07-10 |
CN103186046A (zh) | 2013-07-03 |
KR101409787B1 (ko) | 2014-06-19 |
TW201335129A (zh) | 2013-09-01 |
JP6039396B2 (ja) | 2016-12-07 |
US20130171567A1 (en) | 2013-07-04 |
US8956799B2 (en) | 2015-02-17 |
CN103186046B (zh) | 2015-10-07 |
TWI462897B (zh) | 2014-12-01 |
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