DK200001910A - Iodoniumsalte som latente syredonorer - Google Patents

Iodoniumsalte som latente syredonorer Download PDF

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Publication number
DK200001910A
DK200001910A DK200001910A DKPA200001910A DK200001910A DK 200001910 A DK200001910 A DK 200001910A DK 200001910 A DK200001910 A DK 200001910A DK PA200001910 A DKPA200001910 A DK PA200001910A DK 200001910 A DK200001910 A DK 200001910A
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Prior art keywords
alkyl
acid
compounds
formula
iodonium salts
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DK200001910A
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English (en)
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Schulz Reinhard
Birbaum Jean-Luc
Wolf Jean-Pierre
Ilg Stephan
Yamato Hitoshi
Asakura Toshikage
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Ciba Sc Holding Ag
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Publication of DK176764B1 publication Critical patent/DK176764B1/da

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    • 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
    • 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
    • G03F7/0382—Macromolecular compounds which are rendered insoluble or differentially wettable the macromolecular compound being present in a chemically amplified negative photoresist composition
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/08—Saturated oxiranes
    • C08G65/10—Saturated oxiranes characterised by the catalysts used
    • C08G65/105—Onium compounds
    • 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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • 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
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055—Radiation sensitive composition or product or process of making
    • Y10S430/114—Initiator containing
    • Y10S430/115—Cationic or anionic

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Materials For Photolithography (AREA)
  • Epoxy Resins (AREA)
  • Polymerization Catalysts (AREA)
  • Medicinal Preparation (AREA)

Description

Patentkrav. 1. Målingsfølsom sammensætning indeholdende (a1) en kationisk eller syrekatalytisk polymeriserbar eller tværbindelig forbindelse, eller (a2) en forbindelse, som forøger dens opløselighed i en fremkalder under indvirkning af syre, og
(b) mindst ét diaryliodoniumsalt med formlen I
Figure DK200001910AD00031
(O, hvori X er forgrenet C(3-20)alkyl eller C(3-8)cycloalkyl, X, er hydrogen, lineær C(1-20)alkyl, forgrenet C(3-20)alkyl eller C(3-8)cycloalkyl, med det forbehold, at summen af carbonatomerne i X og X, er mindst 4, Y er lineær C(1-10)alkyl, forgrenet C(3-10)alkyl eller C(3-8)cycloalkyl, A' er en ikke-nukleofil anion valgt fra gruppen (BF4)', (SbF6)', (PF6)', (B(C6F5))4\ C(1-20)alkylsulfonat, C{2-20)haloaikylsulfonat, usubstitueret C(6-10)arylsulfonat, camphersulfonat, C(1-20)perfluoralkylsulfonylmethid, C(1-20)perfluoralkylsul-fonylimid, og C(6-10)arylsulfonat substitueret med halogen, N02, C(1-12)alkyl, C(1-12)halo-alkyl, C(1-12)alkoxy eller med COOR,; og Ri er C(1-20)alkyl, phenyl, benzyl; eller phenyl mono- eller polysubstitueret med C(1-12)alkyl, C(1-12)alkoxy eller med halogen; med det forbehold, at de to phenylringe på iodatomet ikke er identisk substituerede. 2. Strålingsfølsom sammensætning ifølge krav 1, hvori X i forbindelserne med formlen I forgrenet C(4-12)alkyl eller cyclohexyl. 3. Strålingsfølsom sammensætning ifølge krav 1, hvori Y i forbindelserne med formlen I er lineær C(1-6)alkyl eller cyclohexyl. 4. Strålingsfølsom sammensætning ifølge krav 1, hvori A' i forbindelserne med formlen I er en ikke-nucleofil anion valgt fra gruppen (PF6)', (B(C6F5))4\ C(1-12)alkylsulfonat, C(2-12)haloalkylsulfonat, usubstitueret phenylsulfonat, camphersulfonat, C(1-20)perfluoralkylsulfonylmethid, C(1-20)perfluoralkylsulfonylimid og phenylsulfonat sub stitueret med halogen, N02l C(1-12)alkyl, C(1-12)haloalkyl, C(1-12)alkoxy eller med COOR,. 5. Strålingsfølsom sammensætning ifølge krav 1, hvori i forbindelserne med formlen I X er forgrenet C(4-6)alkyl eller cyclohexyl,
Xi er hydrogen eller forgrenet C(4-6)alkyl, Y er lineær C(1-4)alkyl, forgrenet C(3-4)alkyl eller cyclohexyl, A' er en ikke-nucleofil anion, valgt fra gruppen (PF6)', camphersulfonat og C(1-4)alkylsubstitueret phenylsulfonat. 6. Strålingsfølsom sammensætning ifølge krav 1, hvori komponent (a1) er mindst én forbindelse valgt fra gruppen af cycloaliphatiske epoxyforbindelser, glycidylethere, oxethanforbindelser, vinylethere, syretværbindelige melaminresiner, syretværbindelige hydroxymethylenforbindelser og syretværbindelige alkoxymethylenforbindelser. 7. Strålingsfølsom sammensætning ifølge krav 1, hvori komponent (a2) er mindst én forbindelse valgt fra gruppen af cyloaliphatiske copolymerer, 4-hydroxy-phenyl-gruppeholdige copolymerer, maleinsyreanhydridholdige copolymerer, og acrylsyre-, acrylsyreester- og methacrylsyreesterholdige copolymerer, med det forbehold, at disse copolymerer bærer funktionelle grupper, som forøger opløseligheden af polymeren i en basisk fremkalder efter omsætning med en syre. 8. Strålingsfølsom sammensætning ifølge krav 1, som foruden komponenter (a1) eller (a2) og (b) indeholder mindst én sensibilisatorforbindelse (d), især benzophenon, thi-oxanthon, anthracen eller derivater deraf. 9. Anvendelse af en forbindelse med formlen I ifølge krav 1 som fotolatent syredonor i polymerisationen eller tværbindingen af kationisk eller syrekatalytisk polymeriserbare eller tværbindelige forbindelser eller til at forøge opløseligheden af forbindelser, hvis opløselighed forøges i en fremkalder under indvirkning af syre. 10. Fremgangsmåde til fotopolymerisationen eller tværbindingen af kationisk eller syrekatalytisk polymeriserbar eller tværbindelige forbindelser under indvirkning af elektromagnetisk stråling eller en elektronstråle, ved hvilken fremgangsmåde en forbindelse med formlen I ifølge krav 1 anvendes som fotolatent syredonor. 11. Overtrukket substrat, som er overtrukket på mindst én overflade med en sammensætning ifølge krav 1, 12. Fremgangsmåde til fremstilling af reliefbilleder, ved hvilken en sammensætning ifølge krav 1 påføres på et substrat og derefter eksponeres billedvis. 13. Fotoresist indeholdende en forbindelse med formlen I som strålingsfølsom syredonor. 14. Fotoresist ifølge krav 13, hvor fotoresisten er en negativ resist. 15. Fotoresist ifølge krav 13, hvori fotoresisten er en positiv resist. 16. Fotoresist ifølge krav 13, hvori fotoresisten er en kemisk forstærket resist. 17. Anvendelse af en forbindelse med formlen I som strålingsfølsom syredonor ved fremstillingen af overfladeovertrækssammensætninger, pulverovertrækssammensætninger, trykfarver, trykplader, dentalmaterialer, stereolitografiske resiner, klæbestoffer, antiklæbende overtræk, farvefiltre, resistmaterialer eller billedregistreringsmaterialer. 18. Fremgangsmåde ifølge krav 10 ved fremstilling af overfladeovertrækssammensætninger, pulverovertrækssammensætninger, trykfarver, trykplader, dental-materialer, stereolitografiresiner, klæbestoffer, antiklæbende overtræk, farvefiltre, resistmaterialer eller billedregistreringsmaterialer. 19. Forbindelse med formlen I ifølge krav 1.
DK200001910A 1999-12-21 2000-12-20 Strålingsfölsom sammensætning indeholdende et diaryliodoniumsalt, anvendelse af et diaryliodoniumsalt som fotolatent syredonor, fremgangsmåde til polymerisation eller tværbinding, overtrukket substrat, fremgangsmåde til fremstilling af reliefbilleder, DK176764B1 (da)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH234399 1999-12-21
CH234399 1999-12-21

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DK200001910A true DK200001910A (da) 2001-06-22
DK176764B1 DK176764B1 (da) 2009-07-06

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DK200001910A DK176764B1 (da) 1999-12-21 2000-12-20 Strålingsfölsom sammensætning indeholdende et diaryliodoniumsalt, anvendelse af et diaryliodoniumsalt som fotolatent syredonor, fremgangsmåde til polymerisation eller tværbinding, overtrukket substrat, fremgangsmåde til fremstilling af reliefbilleder,

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US (1) US6306555B1 (da)
JP (1) JP4966446B2 (da)
KR (1) KR100753350B1 (da)
CN (1) CN1213343C (da)
AT (1) AT413103B (da)
AU (1) AU778995B2 (da)
BE (1) BE1013871A3 (da)
BR (1) BR0006227B1 (da)
CA (1) CA2328819C (da)
CZ (1) CZ299309B6 (da)
DE (1) DE10063066B4 (da)
DK (1) DK176764B1 (da)
ES (1) ES2181563B1 (da)
FI (1) FI20002767L (da)
FR (1) FR2802539B1 (da)
GB (1) GB2357759B (da)
IT (1) IT1319694B1 (da)
MY (1) MY120646A (da)
NL (1) NL1016959C2 (da)
SE (1) SE522682C2 (da)
SG (1) SG98433A1 (da)
TW (1) TWI225183B (da)

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