JPH032294B2 - - Google Patents
Info
- Publication number
- JPH032294B2 JPH032294B2 JP59171671A JP17167184A JPH032294B2 JP H032294 B2 JPH032294 B2 JP H032294B2 JP 59171671 A JP59171671 A JP 59171671A JP 17167184 A JP17167184 A JP 17167184A JP H032294 B2 JPH032294 B2 JP H032294B2
- Authority
- JP
- Japan
- Prior art keywords
- resin
- resist
- pac
- solubility
- lot
- 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
- 229920003986 novolac Polymers 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 238000001259 photo etching Methods 0.000 claims description 2
- 229920005989 resin Polymers 0.000 description 68
- 239000011347 resin Substances 0.000 description 68
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- 230000010933 acylation Effects 0.000 description 19
- 238000005917 acylation reaction Methods 0.000 description 19
- 238000004090 dissolution Methods 0.000 description 12
- 235000012431 wafers Nutrition 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 9
- 239000003513 alkali Substances 0.000 description 8
- 239000010408 film Substances 0.000 description 7
- 238000011068 loading method Methods 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 230000018109 developmental process Effects 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 238000005266 casting Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 229920002120 photoresistant polymer Polymers 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- VOOLKNUJNPZAHE-UHFFFAOYSA-N formaldehyde;2-methylphenol Chemical group O=C.CC1=CC=CC=C1O VOOLKNUJNPZAHE-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- -1 sulfonate diester Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DEQUKPCANKRTPZ-UHFFFAOYSA-N (2,3-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O DEQUKPCANKRTPZ-UHFFFAOYSA-N 0.000 description 1
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000003679 aging effect Effects 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- 238000005805 hydroxylation reaction Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 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 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000906 photoactive agent Substances 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate 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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
- G03F7/0236—Condensation products of carbonyl compounds and phenolic compounds, e.g. novolak resins
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Materials For Photolithography (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/560,781 US4564575A (en) | 1984-01-30 | 1984-01-30 | Tailoring of novolak and diazoquinone positive resists by acylation of novolak |
| US560781 | 1990-07-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60159847A JPS60159847A (ja) | 1985-08-21 |
| JPH032294B2 true JPH032294B2 (enExample) | 1991-01-14 |
Family
ID=24239347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59171671A Granted JPS60159847A (ja) | 1984-01-30 | 1984-08-20 | ポジテイブ写真食刻レジスト組成 |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4564575A (enExample) |
| EP (1) | EP0150315A3 (enExample) |
| JP (1) | JPS60159847A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101877360B1 (ko) * | 2009-12-15 | 2018-07-11 | 롬 앤드 하스 일렉트로닉 머트어리얼즈 엘엘씨 | 포토레지스트 및 그의 사용방법 |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60260611A (ja) * | 1984-06-08 | 1985-12-23 | Mitsubishi Petrochem Co Ltd | 高分子量クレゾ−ルノボラツク樹脂の製造方法 |
| DE3421448A1 (de) * | 1984-06-08 | 1985-12-12 | Hoechst Ag, 6230 Frankfurt | Perfluoralkylgruppen aufweisende polymere, sie enthaltende reproduktionsschichten und deren verwendung fuer den wasserlosen offsetdruck |
| GB8505402D0 (en) * | 1985-03-02 | 1985-04-03 | Ciba Geigy Ag | Modified phenolic resins |
| US5264319A (en) * | 1985-05-10 | 1993-11-23 | Hitachi, Ltd. | Photosensitive resin composition having high resistance to oxygen plasma, containing alkali-soluble organosilicon polymer and photosensitive dissolution inhibitor |
| CA1279430C (en) * | 1985-12-06 | 1991-01-22 | Takashi Kubota | High-molecular-weight soluble novolak resin and process for preparation thereof |
| US4980264A (en) * | 1985-12-17 | 1990-12-25 | International Business Machines Corporation | Photoresist compositions of controlled dissolution rate in alkaline developers |
| EP0232167B1 (en) * | 1986-02-07 | 1988-12-28 | Nippon Telegraph And Telephone Corporation | Photosensitive and high energy beam sensitive resin composition containing substituted polysiloxane |
| US4902785A (en) * | 1986-05-02 | 1990-02-20 | Hoechst Celanese Corporation | Phenolic photosensitizers containing quinone diazide and acidic halide substituents |
| US4732837A (en) * | 1986-05-02 | 1988-03-22 | Hoechst Celanese Corporation | Novel mixed ester O-quinone photosensitizers |
| US5035976A (en) * | 1986-05-02 | 1991-07-30 | Hoechst Celanese Corporation | Photosensitive article having phenolic photosensitizers containing quinone diazide and acid halide substituents |
| US5162510A (en) * | 1986-05-02 | 1992-11-10 | Hoechst Celanese Corporation | Process for the preparation of photosensitive compositions containing a mixed ester o-quinone photosensitizer |
| US4732836A (en) * | 1986-05-02 | 1988-03-22 | Hoechst Celanese Corporation | Novel mixed ester O-quinone photosensitizers |
| JPS63305348A (ja) * | 1987-06-05 | 1988-12-13 | Fuji Photo Film Co Ltd | ポジ型フオトレジスト組成物 |
| US4927956A (en) * | 1987-09-16 | 1990-05-22 | Hoechst Celanese Corporation | 3,5-disubstituted-4-acetoxystyrene and process for its production |
| US5342727A (en) * | 1988-10-21 | 1994-08-30 | Hoechst Celanese Corp. | Copolymers of 4-hydroxystyrene and alkyl substituted-4-hydroxystyrene in admixture with a photosensitizer to form a photosensitive composition |
| US5023164A (en) * | 1989-10-23 | 1991-06-11 | International Business Machines Corporation | Highly sensitive dry developable deep UV photoresist |
| US5208138A (en) * | 1990-02-05 | 1993-05-04 | Morton International, Inc. | High contrast high thermal stability positive photoresists having novolak resins of lowered hydroxyl content |
| US5182184A (en) * | 1990-02-05 | 1993-01-26 | Morton International, Inc. | Novolak resins of lowered hydroxyl content and high contrast high thermal stability positive photoresists prepared therefrom |
| US5514520A (en) * | 1995-03-16 | 1996-05-07 | Shipley Company, L.L.C. | Radiation sensitive composition comprising polymer having inert blocking groups |
| US5541263A (en) * | 1995-03-16 | 1996-07-30 | Shipley Company, L.L.C. | Polymer having inert blocking groups |
| US5700624A (en) * | 1995-05-09 | 1997-12-23 | Shipley Company, L.L.C. | Positive acid catalyzed resists having an alkali soluble resin with acid labile groups and inert blocking groups |
| US5731386A (en) * | 1995-05-09 | 1998-03-24 | Shipley Company, L.L.C. | Polymer for positive acid catalyzed resists |
| US5652081A (en) * | 1995-09-20 | 1997-07-29 | Fuji Photo Film Co., Ltd. | Positive working photoresist composition |
| US5707782A (en) * | 1996-03-01 | 1998-01-13 | The Board Of Trustees Of The University Of Illinois | Photoimageable, dielectric, crosslinkable copolyesters |
| KR19980087477A (ko) * | 1997-05-30 | 1998-12-05 | 마틴즈 길레모 | 방사선 민감성 중합체 조성물 |
| US5985507A (en) * | 1998-02-18 | 1999-11-16 | Olin Microelectronic Chemicals, Inc. | Selected high thermal novolaks and positive-working radiation-sensitive compositions |
| CN101253449A (zh) * | 2005-08-30 | 2008-08-27 | 日立化成工业株式会社 | 感光性树脂组合物及感光性组件 |
| TWI705991B (zh) * | 2015-12-07 | 2020-10-01 | 日商迪愛生股份有限公司 | 酚醛清漆型樹脂及抗蝕劑膜 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL230099A (enExample) * | 1957-08-01 | |||
| US3802885A (en) * | 1967-08-15 | 1974-04-09 | Algraphy Ltd | Photosensitive lithographic naphthoquinone diazide printing plate with aluminum base |
| JPS5421089B2 (enExample) * | 1973-05-29 | 1979-07-27 | ||
| DE2629996A1 (de) * | 1976-07-03 | 1978-01-05 | Ibm Deutschland | Verfahren zur passivierung und planarisierung eines metallisierungsmusters |
| DE2718254C3 (de) * | 1977-04-25 | 1980-04-10 | Hoechst Ag, 6000 Frankfurt | Strahlungsempfindliche Kopiermasse |
| DE2829511A1 (de) * | 1978-07-05 | 1980-01-24 | Hoechst Ag | Strahlungsempfindliches gemisch und verfahren zur herstellung von reliefbildern |
| DE3009873A1 (de) * | 1979-03-16 | 1980-09-25 | Daicel Chem | Photoempfindliche masse |
| DE2928636A1 (de) * | 1979-07-16 | 1981-02-12 | Hoechst Ag | Strahlungsempfindliches gemisch und verfahren zur herstellung von reliefbildern |
| JPS57120931A (en) * | 1981-01-20 | 1982-07-28 | Japan Synthetic Rubber Co Ltd | Positive type photosensitive resin composition |
-
1984
- 1984-01-30 US US06/560,781 patent/US4564575A/en not_active Expired - Fee Related
- 1984-08-20 JP JP59171671A patent/JPS60159847A/ja active Granted
- 1984-11-27 EP EP84114275A patent/EP0150315A3/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101877360B1 (ko) * | 2009-12-15 | 2018-07-11 | 롬 앤드 하스 일렉트로닉 머트어리얼즈 엘엘씨 | 포토레지스트 및 그의 사용방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0150315A2 (en) | 1985-08-07 |
| US4564575A (en) | 1986-01-14 |
| EP0150315A3 (en) | 1987-04-29 |
| JPS60159847A (ja) | 1985-08-21 |
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