CA1220375A - Resist lithographique a grande resolution et methode de fabrication - Google Patents

Resist lithographique a grande resolution et methode de fabrication

Info

Publication number: CA1220375A
Authority: CA; Canada
Prior art keywords: accordance; vinyl; medium; cationic polymer; poly
Prior art date: 1981-04-20
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

Application number

CA000399440A

Other languages

English (en)

Inventor

William Jensen

Kang I. Lee

Peter Cukor

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Verizon Laboratories Inc

Original Assignee

GTE Laboratories Inc

Priority date (The priority date 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 date listed.)

1981-04-20

Filing date

1982-03-25

Publication date

1987-04-14

1982-03-25 Application filed by GTE Laboratories Inc filed Critical GTE Laboratories Inc

1987-04-14 Application granted granted Critical

1987-04-14 Publication of CA1220375A publication Critical patent/CA1220375A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 20
239000000758 substrate Substances 0.000 claims abstract description 37
238000010894 electron beam technology Methods 0.000 claims abstract description 24
229920002554 vinyl polymer Polymers 0.000 claims abstract description 13
125000003118 aryl group Chemical group 0.000 claims abstract description 7
238000000059 patterning Methods 0.000 claims abstract description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 2
229920006317 cationic polymer Polymers 0.000 claims description 44
-1 poly(2-vinyl-N-methyl pyridinium) Polymers 0.000 claims description 36
239000010408 film Substances 0.000 claims description 33
229920000642 polymer Polymers 0.000 claims description 18
239000002904 solvent Substances 0.000 claims description 15
239000010409 thin film Substances 0.000 claims description 14
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 12
229910052710 silicon Inorganic materials 0.000 claims description 9
239000010703 silicon Substances 0.000 claims description 9
125000002091 cationic group Chemical group 0.000 claims description 6
230000005855 radiation Effects 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
238000005406 washing Methods 0.000 claims description 4
238000001020 plasma etching Methods 0.000 claims description 3
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 1
DZBUGLKDJFMEHC-UHFFFAOYSA-O acridine;hydron Chemical compound C1=CC=CC2=CC3=CC=CC=C3[NH+]=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-O 0.000 claims 1
SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 claims 1
AWJUIBRHMBBTKR-UHFFFAOYSA-O isoquinolin-2-ium Chemical compound C1=[NH+]C=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-O 0.000 claims 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims 1
XSCHRSMBECNVNS-UHFFFAOYSA-O quinoxalin-1-ium Chemical compound [NH+]1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-O 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
150000001298 alcohols Chemical class 0.000 abstract description 4
239000002798 polar solvent Substances 0.000 abstract description 2
230000009466 transformation Effects 0.000 abstract description 2
239000000463 material Substances 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
230000008859 change Effects 0.000 description 9
229920000885 poly(2-vinylpyridine) Polymers 0.000 description 9
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 7
229920000180 alkyd Polymers 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
239000000047 product Substances 0.000 description 7
235000012431 wafers Nutrition 0.000 description 7
238000007429 general method Methods 0.000 description 6
230000035945 sensitivity Effects 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
150000002500 ions Chemical class 0.000 description 4
238000004377 microelectronic Methods 0.000 description 4
206010011416 Croup infectious Diseases 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000004132 cross linking Methods 0.000 description 3
201000010549 croup Diseases 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000010410 layer Substances 0.000 description 3
230000007246 mechanism Effects 0.000 description 3
239000000178 monomer Substances 0.000 description 3
229920002120 photoresistant polymer Polymers 0.000 description 3
229920006254 polymer film Polymers 0.000 description 3
230000008569 process Effects 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
235000009434 Actinidia chinensis Nutrition 0.000 description 2
244000298697 Actinidia deliciosa Species 0.000 description 2
235000009436 Actinidia deliciosa Nutrition 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000005266 casting Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
238000000609 electron-beam lithography Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000009987 spinning Methods 0.000 description 2
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
GCDPERPXPREHJF-UHFFFAOYSA-N 1-iodododecane Chemical compound CCCCCCCCCCCCI GCDPERPXPREHJF-UHFFFAOYSA-N 0.000 description 1
DWMSYQDOPYSCJR-UHFFFAOYSA-M 2-ethenyl-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1C=C DWMSYQDOPYSCJR-UHFFFAOYSA-M 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
108700028369 Alleles Proteins 0.000 description 1
PLKDXPRMXUEDEC-UHFFFAOYSA-N C1=CC=C2N=C(C=CC=C3)C3=CC2=C1.C1=CC=C2N=CN=CC2=C1.C1=CC=C2N=CC=NC2=C1 Chemical compound C1=CC=C2N=C(C=CC=C3)C3=CC2=C1.C1=CC=C2N=CN=CC2=C1.C1=CC=C2N=CC=NC2=C1 PLKDXPRMXUEDEC-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
241000985630 Lota lota Species 0.000 description 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000004020 conductor Substances 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
230000003413 degradative effect Effects 0.000 description 1
230000008021 deposition Effects 0.000 description 1
238000013461 design Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005530 etching Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229910003437 indium oxide Inorganic materials 0.000 description 1
PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
ZSVHUITUMSDFCK-UHFFFAOYSA-N isoquinoline;quinoline Chemical compound C1=NC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 ZSVHUITUMSDFCK-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000001459 lithography Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
238000001393 microlithography Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
238000006116 polymerization reaction Methods 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000011514 reflex Effects 0.000 description 1
238000000646 scanning calorimetry Methods 0.000 description 1
PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 1
230000003068 static effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000002344 surface layer Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000010257 thawing Methods 0.000 description 1
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
229910001887 tin oxide Inorganic materials 0.000 description 1
230000007704 transition Effects 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
- G03F7/008—Azides

Landscapes

Physics & Mathematics (AREA)
General Physics & Mathematics (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Materials For Photolithography (AREA)

CA000399440A 1981-04-20 1982-03-25 Resist lithographique a grande resolution et methode de fabrication Expired CA1220375A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US25593681A	1981-04-20	1981-04-20
US255,936		1981-04-20

Publications (1)

Publication Number	Publication Date
CA1220375A true CA1220375A (fr)	1987-04-14

Family

ID=22970460

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000399440A Expired CA1220375A (fr)	1981-04-20	1982-03-25	Resist lithographique a grande resolution et methode de fabrication

Country Status (3)

Country	Link
JP (1)	JPS57189136A (fr)
CA (1)	CA1220375A (fr)
DE (1)	DE3213771A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS60116132A (ja) *	1983-11-29	1985-06-22	Fujitsu Ltd	ネガ型レジストパタ−ンの形成方法
DE3743743A1 (de) *	1987-12-23	1989-07-06	Basf Ag	Polymere konditionierungsmittel zur vorbehandlung von nichtmetallischen oberflaechen fuer eine chemische metallisierung
US5512418A (en) *	1993-03-10	1996-04-30	E. I. Du Pont De Nemours And Company	Infra-red sensitive aqueous wash-off photoimaging element

1982
- 1982-03-25 CA CA000399440A patent/CA1220375A/fr not_active Expired
- 1982-04-14 DE DE19823213771 patent/DE3213771A1/de not_active Withdrawn
- 1982-04-20 JP JP6485482A patent/JPS57189136A/ja active Pending

Also Published As

Publication number	Publication date
JPS57189136A (en)	1982-11-20
DE3213771A1 (de)	1982-11-25

Legal Events

Date	Code	Title	Description
2004-04-14	MKEX	Expiry

Publication	Publication Date	Title
EP0614123B1 (fr)	1996-10-16	Polymères conducteurs solubles dans l'eau, leur fabrication et emploi
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US6685853B1 (en)	2004-02-03	Energy sensitive electrically conductive admixtures, uses thereof, methods of fabrication and structures fabricated therewith
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US4096290A (en)	1978-06-20	Resist mask formation process with haloalkyl methacrylate copolymers
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US4289842A (en)	1981-09-15	Negative-working polymers useful as electron beam resists
US5153103A (en)	1992-10-06	Resist composition and pattern formation process
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CA1220375A (fr)	1987-04-14	Resist lithographique a grande resolution et methode de fabrication
JPH06298934A (ja)	1994-10-25	高分子量ポリマー被膜形成方法
EP0439289B1 (fr)	1996-10-23	Procédé de formation d'un motif et réserve à utiliser dans ce procédé
KR940001554B1 (ko)	1994-02-24	사진평판의 스트리핑 방법
US4456678A (en)	1984-06-26	High resolution lithographic resist of negative working cationic vinyl polymer
US4262081A (en)	1981-04-14	Fabrication based on radiation sensitive resists of halo-alkyl styrene polymers
KR100418739B1 (ko)	2004-07-05	조절된피에이치를갖는전기전도성중합체를포함하는조성물,상기전기전도성중합체의층을포함하는레지스트구조물,이구조물의제조방법
US7166241B1 (en)	2007-01-23	Water-soluble electrically conducting polymers, their synthesis and use
US4201580A (en)	1980-05-06	Lithographic fabrication with treatment of "living polymer"
US4237208A (en)	1980-12-02	Silane electron beam resists
US5306601A (en)	1994-04-26	Fine pattern forming material and pattern forming method
US4581318A (en)	1986-04-08	N-alkynyl polyvinylpyridinium resists having electron and deep U.V. sensitivity
US4677048A (en)	1987-06-30	Process of using N-alkynyl polyvinylpyridinium resists having electron and deep U.V. sensitivity
EP0348961A2 (fr)	1990-01-03	Matériel et méthode pour la formation de modèles très fins