GB1484061A - Radiation sensitive composition - Google Patents
Radiation sensitive compositionInfo
- Publication number
- GB1484061A GB1484061A GB4136274A GB4136274A GB1484061A GB 1484061 A GB1484061 A GB 1484061A GB 4136274 A GB4136274 A GB 4136274A GB 4136274 A GB4136274 A GB 4136274A GB 1484061 A GB1484061 A GB 1484061A
- Authority
- GB
- United Kingdom
- Prior art keywords
- norbornene
- radiation
- polymer
- sensitive
- carboxylate
- 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
Links
- 230000005855 radiation Effects 0.000 title abstract 6
- 239000000203 mixture Substances 0.000 title abstract 4
- 229920000642 polymer Polymers 0.000 abstract 6
- RMAZRAQKPTXZNL-UHFFFAOYSA-N methyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C2C(C(=O)OC)CC1C=C2 RMAZRAQKPTXZNL-UHFFFAOYSA-N 0.000 abstract 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract 2
- 239000003431 cross linking reagent Substances 0.000 abstract 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 abstract 2
- 150000002848 norbornenes Chemical class 0.000 abstract 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- BMAXQTDMWYDIJX-UHFFFAOYSA-N bicyclo[2.2.1]hept-2-ene-5-carbonitrile Chemical compound C1C2C(C#N)CC1C=C2 BMAXQTDMWYDIJX-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001244 carboxylic acid anhydrides Chemical group 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 150000001925 cycloalkenes Chemical class 0.000 abstract 1
- URYYVOIYTNXXBN-UPHRSURJSA-N cyclooctene Chemical compound C1CCC\C=C/CC1 URYYVOIYTNXXBN-UPHRSURJSA-N 0.000 abstract 1
- 239000004913 cyclooctene Substances 0.000 abstract 1
- VGQLNJWOULYVFV-WZENYGAOSA-N dimethyl (2r,3s)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate Chemical compound C1C2C=CC1[C@H](C(=O)OC)[C@@H]2C(=O)OC VGQLNJWOULYVFV-WZENYGAOSA-N 0.000 abstract 1
- 238000010894 electron beam technology Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 abstract 1
- 229920001519 homopolymer Polymers 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000003949 imides Chemical class 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- VHDXYZOZULHRIL-UHFFFAOYSA-N n,n-dimethylbicyclo[2.2.1]hept-2-ene-5-carboxamide Chemical compound C1C2C(C(=O)N(C)C)CC1C=C2 VHDXYZOZULHRIL-UHFFFAOYSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 239000002534 radiation-sensitizing agent Substances 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 239000010703 silicon Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229920003051 synthetic elastomer Polymers 0.000 abstract 1
- 239000005061 synthetic rubber Substances 0.000 abstract 1
- 239000010409 thin film Substances 0.000 abstract 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
- G03F7/0384—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the main chain of the photopolymer
-
- 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
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- 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
- G03F7/008—Azides
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
1484061 Radiation-sensitive compositions of ring-opened polymers JAPAN SYNTHETIC RUBBER CO Ltd 23 Sept 1974 [27 Sept 1973] 41362/74 Heading C3P [Also in Division G2] Radiation-sensitive compositions comprise a ring-opened polymer of a norbornene derivative having at least one ester, nitrile, carboxyl, amide, imide, hydroxyl or carboxylic acid anhydride group or halogen atom substituent, or a hydrolysis product of the polymer; and a radiation-sensitive cross-linking agent or radiation sensitizer. The polymer may be a homopolymer or copolymer of one or more of said norbornene derivatives and may also include units derived from a cycloolefin other than cyclohexene. Radiation-sensitive azides are preferred as cross-linking agent. In examples the ring-opened polymer is derived from (1) methyl 5 - norbornene - 2 - carboxylate, (2) methyl 5-norbornene-2-carboxylate and 5-norbornene-2-nitrile, (3) N,N-dimethyl-5-norbornene 2-carboxylic acid amide, (4) dimethyl 5- norbornene-2,3-dicarboxylate, (5) the free acid form of polymer (1) obtained by acid hydrolysis, (6) methyl 5-norbornene-2-carboxylate and cyclopentane and (7) 5-norbornene-2-3-dicarboxylic acid anhydride and cyclo-octene. The compositions are suitably applied as a thin film to a metal plate or silicon wafer, imagewise exposed to radiation such as light or an electron beam, and developed with a solvent to produce resist images which have applications in printed circuits, name plates, integrated circuits and plate-making.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10875373A JPS5628257B2 (en) | 1973-09-27 | 1973-09-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1484061A true GB1484061A (en) | 1977-08-24 |
Family
ID=14492620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4136274A Expired GB1484061A (en) | 1973-09-27 | 1974-09-23 | Radiation sensitive composition |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5628257B2 (en) |
| DE (1) | DE2445395A1 (en) |
| GB (1) | GB1484061A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1031879A1 (en) * | 1999-02-25 | 2000-08-30 | Shin-Etsu Chemical Co., Ltd. | Novel ester compounds, polymers, resist compositions and patterning process |
| US6291131B1 (en) | 1998-08-26 | 2001-09-18 | Hyundai Electronics Industries Co., Ltd. | Monomers for photoresist, polymers thereof, and photoresist compositions using the same |
| US6312865B1 (en) | 1997-12-31 | 2001-11-06 | Hyundai Electronics Industries Co., Ltd. | Semiconductor device using polymer-containing photoresist, and process for manufacturing the same |
| US6369181B1 (en) | 1997-12-29 | 2002-04-09 | Hyundai Electronics Industries Co., Ltd. | Copolymer resin, preparation thereof, and photoresist using the same |
| US6391518B1 (en) | 1998-07-27 | 2002-05-21 | Hyundai Electronics Industries Co., Ltd. | Polymers and photoresist compositions using the same |
| US6410670B1 (en) | 1998-08-26 | 2002-06-25 | Hyundai Electronics Industries Co., Ltd. | Photoresist monomer having hydroxy group and carboxy group, copolymer thereof and photoresist composition using the same |
| US6569971B2 (en) | 1998-08-27 | 2003-05-27 | Hyundai Electronics Industries Co., Ltd. | Polymers for photoresist and photoresist compositions using the same |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1489470A (en) * | 1974-07-04 | 1977-10-19 | Showa Denko Kk | Norbornene polymers |
| US4440850A (en) * | 1981-07-23 | 1984-04-03 | Ciba-Geigy Corporation | Photopolymerisation process with two exposures of a single layer |
| US4571375A (en) * | 1983-10-24 | 1986-02-18 | Benedikt George M | Ring-opened polynorbornene negative photoresist with bisazide |
-
1973
- 1973-09-27 JP JP10875373A patent/JPS5628257B2/ja not_active Expired
-
1974
- 1974-09-23 DE DE19742445395 patent/DE2445395A1/en not_active Withdrawn
- 1974-09-23 GB GB4136274A patent/GB1484061A/en not_active Expired
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6369181B1 (en) | 1997-12-29 | 2002-04-09 | Hyundai Electronics Industries Co., Ltd. | Copolymer resin, preparation thereof, and photoresist using the same |
| US6608158B2 (en) | 1997-12-29 | 2003-08-19 | Hyundai Electronics Industries Co., Ltd. | Copolymer resin, preparation thereof, and photoresist using the same |
| US6312865B1 (en) | 1997-12-31 | 2001-11-06 | Hyundai Electronics Industries Co., Ltd. | Semiconductor device using polymer-containing photoresist, and process for manufacturing the same |
| US6632903B2 (en) | 1997-12-31 | 2003-10-14 | Hyundai Electronics Industries Co., Ltd. | Polymer-containing photoresist, and process for manufacturing the same |
| US6391518B1 (en) | 1998-07-27 | 2002-05-21 | Hyundai Electronics Industries Co., Ltd. | Polymers and photoresist compositions using the same |
| US6291131B1 (en) | 1998-08-26 | 2001-09-18 | Hyundai Electronics Industries Co., Ltd. | Monomers for photoresist, polymers thereof, and photoresist compositions using the same |
| US6410670B1 (en) | 1998-08-26 | 2002-06-25 | Hyundai Electronics Industries Co., Ltd. | Photoresist monomer having hydroxy group and carboxy group, copolymer thereof and photoresist composition using the same |
| US6586619B2 (en) | 1998-08-26 | 2003-07-01 | Hyundai Electronics Industries Co., Ltd. | Photoresist monomer having hydroxy group and carboxy group, copolymer thereof and photoresist composition using the same |
| US6569971B2 (en) | 1998-08-27 | 2003-05-27 | Hyundai Electronics Industries Co., Ltd. | Polymers for photoresist and photoresist compositions using the same |
| US6987155B2 (en) | 1998-08-27 | 2006-01-17 | Hyundai Electronics Industries Co., Ltd. | Polymers for photoresist and photoresist compositions using the same |
| EP1031879A1 (en) * | 1999-02-25 | 2000-08-30 | Shin-Etsu Chemical Co., Ltd. | Novel ester compounds, polymers, resist compositions and patterning process |
| US6284429B1 (en) | 1999-02-25 | 2001-09-04 | Shin-Etsu Chemical Co., Ltd. | Ester compounds, polymers, resist compositions and patterning process |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2445395A1 (en) | 1975-04-10 |
| JPS5628257B2 (en) | 1981-06-30 |
| JPS5060221A (en) | 1975-05-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 746 | Register noted 'licences of right' (sect. 46/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |