JPH0650396B2 - ポジ型ホトレジスト組成物 - Google Patents
ポジ型ホトレジスト組成物Info
- Publication number
- JPH0650396B2 JPH0650396B2 JP60174316A JP17431685A JPH0650396B2 JP H0650396 B2 JPH0650396 B2 JP H0650396B2 JP 60174316 A JP60174316 A JP 60174316A JP 17431685 A JP17431685 A JP 17431685A JP H0650396 B2 JPH0650396 B2 JP H0650396B2
- Authority
- JP
- Japan
- Prior art keywords
- pattern
- cresol
- weight
- positive photoresist
- photoresist composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920002120 photoresistant polymer Polymers 0.000 title claims description 24
- 239000000203 mixture Substances 0.000 title claims description 19
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 22
- 229930003836 cresol Natural products 0.000 claims description 22
- 229920003986 novolac Polymers 0.000 claims description 19
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 12
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 12
- 239000003504 photosensitizing agent Substances 0.000 claims description 10
- QVEIBLDXZNGPHR-UHFFFAOYSA-N naphthalene-1,4-dione;diazide Chemical compound [N-]=[N+]=[N-].[N-]=[N+]=[N-].C1=CC=C2C(=O)C=CC(=O)C2=C1 QVEIBLDXZNGPHR-UHFFFAOYSA-N 0.000 claims description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 14
- 239000004065 semiconductor Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 6
- 238000005530 etching Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- -1 naphthoquinone diazide sulfonic acid ester Chemical class 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ZDOIAPGLORMKTR-UHFFFAOYSA-N 2-Hydroxyfluorene Chemical compound C1=CC=C2C3=CC=C(O)C=C3CC2=C1 ZDOIAPGLORMKTR-UHFFFAOYSA-N 0.000 description 2
- YPWLZGITFNGGKW-UHFFFAOYSA-N 2-phenanthrol Chemical compound C1=CC=C2C3=CC=C(O)C=C3C=CC2=C1 YPWLZGITFNGGKW-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 150000001896 cresols Chemical class 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000001312 dry etching Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000007261 regionalization Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- JQCWLRHNAHIIGW-UHFFFAOYSA-N 2,8-dimethylnonan-5-one Chemical compound CC(C)CCC(=O)CCC(C)C JQCWLRHNAHIIGW-UHFFFAOYSA-N 0.000 description 1
- XXXFZKQPYACQLD-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl acetate Chemical compound CC(=O)OCCOCCO XXXFZKQPYACQLD-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- LYKRPDCJKSXAHS-UHFFFAOYSA-N phenyl-(2,3,4,5-tetrahydroxyphenyl)methanone Chemical compound OC1=C(O)C(O)=CC(C(=O)C=2C=CC=CC=2)=C1O LYKRPDCJKSXAHS-UHFFFAOYSA-N 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Materials For Photolithography (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60174316A JPH0650396B2 (ja) | 1985-08-09 | 1985-08-09 | ポジ型ホトレジスト組成物 |
| DE19863626582 DE3626582A1 (de) | 1985-08-09 | 1986-08-06 | Positiv arbeitende photoresistzusammensetzung |
| GB08619368A GB2180842B (en) | 1985-08-09 | 1986-08-08 | A novel positive-working photoresist composition |
| US07/935,131 US5281508A (en) | 1985-08-09 | 1992-08-21 | Positive-working photoresist containing o-naphthoquinone diazide sulfonic acid ester and novolak resin consisting of 35 to 43% m-cresol and 65 to 57% p-cresol with substantial absence of o-cresol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60174316A JPH0650396B2 (ja) | 1985-08-09 | 1985-08-09 | ポジ型ホトレジスト組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6235349A JPS6235349A (ja) | 1987-02-16 |
| JPH0650396B2 true JPH0650396B2 (ja) | 1994-06-29 |
Family
ID=15976518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60174316A Expired - Lifetime JPH0650396B2 (ja) | 1985-08-09 | 1985-08-09 | ポジ型ホトレジスト組成物 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPH0650396B2 (enrdf_load_stackoverflow) |
| DE (1) | DE3626582A1 (enrdf_load_stackoverflow) |
| GB (1) | GB2180842B (enrdf_load_stackoverflow) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0650396B2 (ja) * | 1985-08-09 | 1994-06-29 | 東京応化工業株式会社 | ポジ型ホトレジスト組成物 |
| US5281508A (en) * | 1985-08-09 | 1994-01-25 | Tokyo Ohka Kogyo Co., Ltd. | Positive-working photoresist containing o-naphthoquinone diazide sulfonic acid ester and novolak resin consisting of 35 to 43% m-cresol and 65 to 57% p-cresol with substantial absence of o-cresol |
| JPH0654391B2 (ja) * | 1987-03-06 | 1994-07-20 | 住友化学工業株式会社 | 電子線又はｘ線用ポジ型レジスト組成物 |
| JP2693472B2 (ja) * | 1987-11-26 | 1997-12-24 | 株式会社東芝 | レジスト |
| JP2618940B2 (ja) * | 1987-11-27 | 1997-06-11 | 東京応化工業株式会社 | ポジ型ホトレジスト組成物 |
| JP2618947B2 (ja) * | 1988-01-08 | 1997-06-11 | 東京応化工業株式会社 | ポジ型ホトレジスト組成物 |
| DE3839906A1 (de) * | 1987-11-27 | 1989-06-08 | Tokyo Ohka Kogyo Co Ltd | Positiv arbeitende lichtempfindliche zusammensetzung, verfahren zu ihrer herstellung und ihre verwendung |
| JPH0658530B2 (ja) * | 1988-04-22 | 1994-08-03 | 東京応化工業株式会社 | ポジ型感光性組成物 |
| JP2505033B2 (ja) * | 1988-11-28 | 1996-06-05 | 東京応化工業株式会社 | 電子線レジスト組成物及びそれを用いた微細パタ―ンの形成方法 |
| JPH02222955A (ja) * | 1989-02-23 | 1990-09-05 | Tokyo Ohka Kogyo Co Ltd | ポジ型感光性組成物 |
| JPH03253859A (ja) * | 1990-03-05 | 1991-11-12 | Fuji Photo Film Co Ltd | 感電離放射線性樹脂組成物 |
| JP2919142B2 (ja) * | 1990-12-27 | 1999-07-12 | 株式会社東芝 | 感光性組成物およびそれを用いたパターン形成方法 |
| JP2935223B2 (ja) * | 1992-04-14 | 1999-08-16 | 東京応化工業株式会社 | レジストパターン形成用材料の製造方法及びタンタルのパターン形成方法 |
| US5332647A (en) * | 1992-08-26 | 1994-07-26 | Tokyo Ohka Kogyo Co., Ltd. | Positive-working quinone diazide composition containing N,N',N"-substituted isocyanurate compound and associated article |
| JP3562673B2 (ja) | 1996-01-22 | 2004-09-08 | 富士写真フイルム株式会社 | ポジ型フォトレジスト組成物 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2616992C3 (de) * | 1976-04-17 | 1987-10-22 | Agfa-Gevaert Ag, 5090 Leverkusen | Lichtempfindliches Kopiermaterial zur Herstellung von Reliefs |
| JPS561045A (en) * | 1979-06-16 | 1981-01-08 | Konishiroku Photo Ind Co Ltd | Photosensitive composition |
| EP0070624B1 (en) * | 1981-06-22 | 1986-11-20 | Philip A. Hunt Chemical Corporation | Novolak resin and a positive photoresist composition containing the same |
| JPS5817112A (ja) * | 1981-06-22 | 1983-02-01 | フイリツプ・エイ・ハント・ケミカル・コ−ポレイシヨン | ポジ型ノボラツクホトレジスト組成物及びその調製物 |
| CA1255952A (en) * | 1983-03-04 | 1989-06-20 | Akihiro Furuta | Positive type photoresist composition |
| JPS6057339A (ja) * | 1983-09-08 | 1985-04-03 | Sumitomo Chem Co Ltd | ポジ型フォトレジスト組成物 |
| EP0148787A3 (en) * | 1984-01-10 | 1987-05-06 | Japan Synthetic Rubber Co., Ltd. | Positive type photosensitive resin composition |
| JPS616647A (ja) * | 1984-06-20 | 1986-01-13 | Konishiroku Photo Ind Co Ltd | ポジ型感光性平版印刷版用感光性組成物 |
| JPH0650396B2 (ja) * | 1985-08-09 | 1994-06-29 | 東京応化工業株式会社 | ポジ型ホトレジスト組成物 |
| US5281508A (en) * | 1985-08-09 | 1994-01-25 | Tokyo Ohka Kogyo Co., Ltd. | Positive-working photoresist containing o-naphthoquinone diazide sulfonic acid ester and novolak resin consisting of 35 to 43% m-cresol and 65 to 57% p-cresol with substantial absence of o-cresol |
-
1985
- 1985-08-09 JP JP60174316A patent/JPH0650396B2/ja not_active Expired - Lifetime
-
1986
- 1986-08-06 DE DE19863626582 patent/DE3626582A1/de active Granted
- 1986-08-08 GB GB08619368A patent/GB2180842B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3626582C2 (enrdf_load_stackoverflow) | 1989-03-09 |
| GB8619368D0 (en) | 1986-09-17 |
| GB2180842B (en) | 1988-07-06 |
| JPS6235349A (ja) | 1987-02-16 |
| DE3626582A1 (de) | 1987-02-19 |
| GB2180842A (en) | 1987-04-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |