TW202337879A - 羧酸鹽、羧酸產生劑、樹脂、抗蝕劑組成物以及抗蝕劑圖案的製造方法 - Google Patents
羧酸鹽、羧酸產生劑、樹脂、抗蝕劑組成物以及抗蝕劑圖案的製造方法 Download PDFInfo
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- 150000007942 carboxylates Chemical class 0.000 title claims abstract description 469
- 239000000203 mixture Substances 0.000 title claims abstract description 269
- 239000011347 resin Substances 0.000 title claims abstract description 225
- 229920005989 resin Polymers 0.000 title claims abstract description 225
- 150000001735 carboxylic acids Chemical class 0.000 title claims abstract 4
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 132
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 129
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 126
- 125000001424 substituent group Chemical group 0.000 claims abstract description 79
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 32
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 781
- -1 Alkane lactone Chemical class 0.000 claims description 750
- 125000000217 alkyl group Chemical group 0.000 claims description 257
- 125000002723 alicyclic group Chemical group 0.000 claims description 255
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 219
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 135
- 125000001153 fluoro group Chemical group F* 0.000 claims description 128
- 229910052731 fluorine Inorganic materials 0.000 claims description 123
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 110
- 150000003839 salts Chemical class 0.000 claims description 104
- 229910052799 carbon Inorganic materials 0.000 claims description 88
- 125000003545 alkoxy group Chemical group 0.000 claims description 87
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 60
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 55
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- 125000001931 aliphatic group Chemical group 0.000 claims description 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
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- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 23
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- 238000000034 method Methods 0.000 claims description 18
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- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 59
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 45
- 150000001768 cations Chemical class 0.000 description 43
- 239000002585 base Substances 0.000 description 40
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 39
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 36
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 35
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 35
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- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 31
- 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 30
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- 230000015572 biosynthetic process Effects 0.000 description 27
- 238000003786 synthesis reaction Methods 0.000 description 27
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 26
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- 238000003756 stirring Methods 0.000 description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 25
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- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 24
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 24
- 125000003118 aryl group Chemical group 0.000 description 23
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 23
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- 238000006116 polymerization reaction Methods 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 18
- 229910052801 chlorine Inorganic materials 0.000 description 18
- 125000001309 chloro group Chemical group Cl* 0.000 description 18
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 18
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 18
- 239000010410 layer Substances 0.000 description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 17
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 17
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 16
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 16
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 16
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 238000001228 spectrum Methods 0.000 description 16
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 16
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 15
- 125000004414 alkyl thio group Chemical group 0.000 description 15
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 15
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 125000003710 aryl alkyl group Chemical group 0.000 description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 14
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 150000001734 carboxylic acid salts Chemical class 0.000 description 12
- 125000001624 naphthyl group Chemical group 0.000 description 12
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 12
- JAMNSIXSLVPNLC-UHFFFAOYSA-N (4-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1 JAMNSIXSLVPNLC-UHFFFAOYSA-N 0.000 description 11
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 11
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- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 10
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
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- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 10
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 10
- 125000005008 perfluoropentyl group Chemical group FC(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 10
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- 150000008053 sultones Chemical group 0.000 description 10
- 125000005023 xylyl group Chemical group 0.000 description 10
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 9
- 235000010290 biphenyl Nutrition 0.000 description 9
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- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 description 9
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 9
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 9
- 238000010894 electron beam technology Methods 0.000 description 9
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 9
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- 125000004093 cyano group Chemical group *C#N 0.000 description 8
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- 239000006228 supernatant Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 7
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 7
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 238000011161 development Methods 0.000 description 7
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- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
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- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 6
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 6
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 6
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- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 6
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- GOIIVCHICYNWSG-UHFFFAOYSA-N 3-(4-ethylphenyl)prop-2-enoic acid Chemical compound CCC1=CC=C(C=CC(O)=O)C=C1 GOIIVCHICYNWSG-UHFFFAOYSA-N 0.000 description 4
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- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
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- RMADLJKIXOWZMV-UHFFFAOYSA-N 4-ethenyl-1,2-diethoxybenzene Chemical compound CCOC1=CC=C(C=C)C=C1OCC RMADLJKIXOWZMV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 238000004458 analytical method Methods 0.000 description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
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- 125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
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- 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
- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/30—Imagewise removal using liquid means
- G03F7/32—Liquid compositions therefor, e.g. developers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
- C08F2800/10—Copolymer characterised by the proportions of the comonomers expressed as molar percentages
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/50—Chemical modification of a polymer wherein the polymer is a copolymer and the modification is taking place only on one or more of the monomers present in minority
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Materials For Photolithography (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2022-054623 | 2022-03-29 | ||
| JP2022054623 | 2022-03-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW202337879A true TW202337879A (zh) | 2023-10-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW112111202A TW202337879A (zh) | 2022-03-29 | 2023-03-24 | 羧酸鹽、羧酸產生劑、樹脂、抗蝕劑組成物以及抗蝕劑圖案的製造方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US20230314939A1 (https=) |
| JP (1) | JP2023147263A (https=) |
| KR (1) | KR20230140428A (https=) |
| TW (1) | TW202337879A (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12578639B2 (en) * | 2021-11-09 | 2026-03-17 | Sumitomo Chemical Company, Limited | Carboxylate, carboxylic acid generator, resin, resist composition and method for producing resist pattern |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011081107A (ja) | 2009-10-06 | 2011-04-21 | Suruga Production Platform Co Ltd | 光ファイバと光デバイスとの光軸調整方法 |
-
2023
- 2023-03-24 TW TW112111202A patent/TW202337879A/zh unknown
- 2023-03-27 US US18/190,650 patent/US20230314939A1/en active Pending
- 2023-03-27 JP JP2023050381A patent/JP2023147263A/ja active Pending
- 2023-03-28 KR KR1020230040627A patent/KR20230140428A/ko active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| KR20230140428A (ko) | 2023-10-06 |
| US20230314939A1 (en) | 2023-10-05 |
| JP2023147263A (ja) | 2023-10-12 |
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