CA1202148A - Photoresist - Google Patents

Photoresist

Info

Publication number: CA1202148A
Authority: CA; Canada
Prior art keywords: photoresist material; copolymer; polymer; isopropenylnaphthalene; component
Prior art date: 1982-05-31
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

CA000429204A

Other languages

English (en)

Inventor

Naohiro Murayama

Teruo Sakagami

Hideaki Doi

Kenichi Kokubun

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.)

Kureha Corp

Original Assignee

Kureha Corp

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.)

1982-05-31

Filing date

1983-05-30

Publication date

1986-03-18

1982-05-31 Priority claimed from JP9276682A external-priority patent/JPS58209732A/ja

1982-09-13 Priority claimed from JP15936482A external-priority patent/JPS5948759A/ja

1983-05-30 Application filed by Kureha Corp filed Critical Kureha Corp

1986-03-18 Application granted granted Critical

1986-03-18 Publication of CA1202148A publication Critical patent/CA1202148A/fr

Status Expired legal-status Critical Current

Links

239000000463 material Substances 0.000 title claims abstract description 49
229920002120 photoresistant polymer Polymers 0.000 title claims abstract description 38
ANCUXNXTHQXICN-UHFFFAOYSA-N 2-prop-1-en-2-ylnaphthalene Chemical compound C1=CC=CC2=CC(C(=C)C)=CC=C21 ANCUXNXTHQXICN-UHFFFAOYSA-N 0.000 claims abstract description 46
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims abstract description 44
229920000642 polymer Polymers 0.000 claims abstract description 27
238000006467 substitution reaction Methods 0.000 claims abstract description 22
230000009477 glass transition Effects 0.000 claims abstract description 19
230000005855 radiation Effects 0.000 claims abstract description 13
229920001577 copolymer Polymers 0.000 claims description 58
239000000203 mixture Substances 0.000 claims description 26
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
238000006116 polymerization reaction Methods 0.000 claims description 14
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 claims description 7
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 7
229940061627 chloromethyl methyl ether Drugs 0.000 claims description 7
229920001519 homopolymer Polymers 0.000 claims description 7
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 2
150000003440 styrenes Chemical class 0.000 claims description 2
125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims 1
230000035945 sensitivity Effects 0.000 abstract description 35
238000001312 dry etching Methods 0.000 abstract description 10
238000005530 etching Methods 0.000 abstract description 5
239000004065 semiconductor Substances 0.000 abstract description 5
238000004519 manufacturing process Methods 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
239000000758 substrate Substances 0.000 description 14
239000000178 monomer Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
238000010894 electron beam technology Methods 0.000 description 9
238000000034 method Methods 0.000 description 9
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 8
239000011248 coating agent Substances 0.000 description 8
238000000576 coating method Methods 0.000 description 8
229910052710 silicon Inorganic materials 0.000 description 8
239000010703 silicon Substances 0.000 description 8
235000012431 wafers Nutrition 0.000 description 8
239000004793 Polystyrene Substances 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
229920002223 polystyrene Polymers 0.000 description 7
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
125000001624 naphthyl group Chemical group 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
238000007265 chloromethylation reaction Methods 0.000 description 4
230000000052 comparative effect Effects 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
206010001497 Agitation Diseases 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000013019 agitation Methods 0.000 description 3
125000000129 anionic group Chemical group 0.000 description 3
239000000470 constituent Substances 0.000 description 3
238000001459 lithography Methods 0.000 description 3
238000010550 living polymerization reaction Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000004528 spin coating Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
239000011651 chromium Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
239000003999 initiator Substances 0.000 description 2
238000010884 ion-beam technique Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
238000002156 mixing Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
239000010453 quartz Substances 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
150000008360 acrylonitriles Chemical class 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
101150089929 figl-1 gene Proteins 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000011090 industrial biotechnology method and process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
238000000206 photolithography Methods 0.000 description 1
239000002685 polymerization catalyst Substances 0.000 description 1
239000003505 polymerization initiator Substances 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
JHJUUEHSAZXEEO-UHFFFAOYSA-M sodium;4-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=C(S([O-])(=O)=O)C=C1 JHJUUEHSAZXEEO-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000002834 transmittance Methods 0.000 description 1
239000008096 xylene 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable

Landscapes

Physics & Mathematics (AREA)
Spectroscopy & Molecular Physics (AREA)
General Physics & Mathematics (AREA)
Materials For Photolithography (AREA)
Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)

CA000429204A 1982-05-31 1983-05-30 Photoresist Expired CA1202148A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP92766/1982		1982-05-31
JP9276682A JPS58209732A (ja)	1982-05-31	1982-05-31	感放射線組成物及びレジスト
JP15936482A JPS5948759A (ja)	1982-09-13	1982-09-13	フオトレジスト材料
JP159364/1982		1982-09-13

Publications (1)

Publication Number	Publication Date
CA1202148A true CA1202148A (fr)	1986-03-18

Family

ID=26434141

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000429204A Expired CA1202148A (fr)	1982-05-31	1983-05-30	Photoresist

Country Status (4)

Country	Link
CA (1)	CA1202148A (fr)
DE (1)	DE3319558C2 (fr)
FR (1)	FR2527795B1 (fr)
GB (1)	GB2125418B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE102005033852A1 (de) *	2005-07-12	2007-01-18	Hach Lange Gmbh	Scheibenförmiges Trägersystem mit einer Mehrzahl integrierter Beugungsstrukturen

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4262081A (en) *	1979-11-21	1981-04-14	Bell Telephone Laboratories, Incorporated	Fabrication based on radiation sensitive resists of halo-alkyl styrene polymers
EP0051320B1 (fr) *	1980-11-05	1986-06-04	Nec Corporation	Composition de réserve négative sensible aux rayons

1983
- 1983-05-30 CA CA000429204A patent/CA1202148A/fr not_active Expired
- 1983-05-30 DE DE19833319558 patent/DE3319558C2/de not_active Expired
- 1983-05-31 FR FR8309023A patent/FR2527795B1/fr not_active Expired
- 1983-05-31 GB GB08314989A patent/GB2125418B/en not_active Expired

Also Published As

Publication number	Publication date
GB8314989D0 (en)	1983-07-06
GB2125418B (en)	1985-09-11
GB2125418A (en)	1984-03-07
FR2527795B1 (fr)	1985-07-26
DE3319558A1 (de)	1983-12-01
DE3319558C2 (de)	1986-10-30
FR2527795A1 (fr)	1983-12-02

Legal Events

Date	Code	Title	Description
2003-05-30	MKEX	Expiry

Publication	Publication Date	Title
JPS6048022B2 (ja)	1985-10-24	電子感応レジスト
US4318976A (en)	1982-03-09	High gel rigidity, negative electron beam resists
CA1202148A (fr)	1986-03-18	Photoresist
US4504631A (en)	1985-03-12	Photoresist material
CA1312843C (fr)	1993-01-19	Fabrication de dispositifs electroniques a l'iade de techniques lithographiques
US4965340A (en)	1990-10-23	Copolymer from sulfur dioxide and vinyl compound
US4523000A (en)	1985-06-11	Copolymers, process for the preparation thereof and ionizing radiation sensitive resist using such copolymers
US4795692A (en)	1989-01-03	Negative-working polymers useful as X-ray or E-beam resists
US4367281A (en)	1983-01-04	Fine fabrication process using radiation sensitive resist
US4414313A (en)	1983-11-08	Sensitive positive electron beam resists
JPH0527106B2 (fr)	1993-04-20
JPS63271253A (ja)	1988-11-09	高解像度ポジ型放射線感応性レジスト
US4054452A (en)	1977-10-18	Method of imaging a layer containing copolymer of glycidyl methacrylate and allyl glycidyl ether
US4888392A (en)	1989-12-19	Copolymer of sulfur dioxide and polyalkylpolysilylstyrene
JPH05331289A (ja)	1993-12-14	二酸化硫黄と核置換スチレン誘導体との共重合体
JPH01155336A (ja)	1989-06-19	放射線感応性樹脂
JPS6349213B2 (fr)	1988-10-04
JPS59192245A (ja)	1984-10-31	レジスト材料
JPS62951A (ja)	1987-01-06	放射線感応性レジスト用材料
JPS59148056A (ja)	1984-08-24	高エネルギ−線感応材料及びその使用方法
JPH0377985B2 (fr)	1991-12-12
JPS649614B2 (fr)	1989-02-17
JPS62215628A (ja)	1987-09-22	二酸化硫黄と核置換トリアルキルシリルスチレンとの共重合体及びその製造方法
JPS60212755A (ja)	1985-10-25	感放射線材料
JPS5857734B2 (ja)	1983-12-21	皮膜形成方法法