WO2001055789A2 - Resine amplifiee chimiquement et soumise a des ondes courtes - Google Patents

Resine amplifiee chimiquement et soumise a des ondes courtes Download PDF

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Publication number
WO2001055789A2
WO2001055789A2 PCT/EP2001/000824 EP0100824W WO0155789A2 WO 2001055789 A2 WO2001055789 A2 WO 2001055789A2 EP 0100824 W EP0100824 W EP 0100824W WO 0155789 A2 WO0155789 A2 WO 0155789A2
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WO
WIPO (PCT)
Prior art keywords
polymer
resist
resist according
tert
groups
Prior art date
Application number
PCT/EP2001/000824
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English (en)
Other versions
WO2001055789A3 (fr
Inventor
Wolf-Dieter Domke
Stefan Hien
Ernst Richter
Michael Sebald
Original Assignee
Infineon Technologies Ag
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.)
Filing date
Publication date
Application filed by Infineon Technologies Ag filed Critical Infineon Technologies Ag
Publication of WO2001055789A2 publication Critical patent/WO2001055789A2/fr
Publication of WO2001055789A3 publication Critical patent/WO2001055789A3/fr

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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
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • 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

Definitions

  • This invention relates to chemically amplified resists
  • Chemical amplified resists (chemical amplification resists;
  • blocking groups are tert-butoxycarbonyloxy (t-BOC) or acetal groups.
  • amplified photo resists result in a poor resolution capability
  • the resist according to the invention is applied to a
  • Patternwise exposure generates acid in the exposed parts of
  • the exposure can be done optically with radiation
  • the appropriate wavelength e. g. ultra-violet light, X-
  • PEB Post Exposure Bake
  • the resist film thus becomes soluble in an alkaline
  • TMAH TMAH hydroxide
  • the exposed areas of the resist film is achieved.
  • the imagewise convertible film-forming polymer is a polymer
  • solubility in the main chain and/or in a side-chain which can
  • the acid-labile groups deblocking groups can include ester
  • acid-labile groups additional groups to improve the
  • the imagewise convertible polymer is not critical.
  • the polymer can contain partially or completely
  • the weight average molecular weight of the polymer can
  • the imagewise convertible polymer is preferably a
  • copolymer having polymer units with acid-labile groups
  • At least one polymer unit selected from the group consisting of:
  • the polymer units are defined according to the monomer from
  • the acid-labile polymer units (I) are polymer units
  • the adhesion-promoting polymer units (II) are polymer units
  • the thermally stable polymer units (III) are polymer units substituted with aromatic, cycloaliphatic, aliphatic or
  • thermally stable polymer units (III) make
  • the reactive polymer units (IV) are polymer units substituted
  • polyfunctional agents such as diamines, and
  • Reactive polymer units (IV) can also be substituted with radical scavenging groups such as
  • the polymer units (V) modifying thermal properties are polymer
  • the photo acid generator according to this invention is a
  • generator compound can be ionic or covalent, and is typically
  • the acid preferably has a pK a in the range
  • photo acid generator compounds includes
  • onium compounds comprising sulfonium salts R 3 S * X " and iodonium
  • radicals R are identical or different, and each denote an aliphatic, aromatic or aryl-carbonyl-alkylene
  • R represents C _ to C 12 .alkyl
  • radicals can include N, 0 or S atoms, or two radicals R
  • R can also be monosubstituted or polysubstituted by OH, N0 2 ,
  • aromatic radicals R can be any aromatic radicals. Furthermore, the aromatic radicals R can be any aromatic radicals. Furthermore, the aromatic radicals R can be any aromatic radicals. Furthermore, the aromatic radicals R can be any aromatic radicals. Furthermore, the aromatic radicals R can be any aromatic radicals R. Furthermore, the aromatic radicals R can be any aromatic radicals R. Furthermore, the aromatic radicals R can be any aromatic radicals R. Furthermore, the aromatic radicals R can be any aromatic radicals R.
  • the anion X " of the onium salt can be:
  • aliphatic sulfonate group in particular a C x _ to C 12 .
  • alkylsulfonate group for example a trifluoromethanesulfonate or nonafluorobutanesulfonate group
  • arylsulfonate group for example a benzenesulfonate or
  • aromatic sulfonate group in particular a fluorinated C s _ to
  • C 4 .alkyl for example a toluenesulfonate group.
  • anion X can also have the following meaning:
  • C x . to C 16 .alkyl- or -cycloalkylsulfonate group for example a hexadecylsulfonate, cyclohexanesulfonate or
  • camphorsulfonate group (C 10 H ls O-SO 3 -) ;
  • arylsulfonate group for example a benzenesulfonate or
  • Particularly preferred sulfonic acids include p-
  • alkanesulfonic acids such as trifluoromethanesulfonic acid
  • the quantity of photoacid generator used in the resist is no
  • PEB bake
  • levels of photoacid generator are in the range from 1% to 6%
  • photoactive onium compound (B) is preferably in the range
  • the radical scavenger according to this invention can be any radical scavenger according to this invention.
  • molecular weight ranging from 500 to 10000, preferably 2000 to
  • the radical scavenger can also be provided as an
  • radical scavengers can be used, provided that they are soluble in the solvent of the resist.
  • scavenger absorbs crosslinking-inducing radicals formed during
  • butylphenyl) -sulfide hydroquinone ; tert-butylhydroquinone;
  • Aromatic amines e. g. aniline-acetone-condensation products
  • Phosphorus compounds e. g. phosphonite
  • biphenylendiphosphonite bis (2, 4 -di-tert-
  • Sterically hindered amines e. g. 2,2,6,6,-
  • Nitroso compounds e. g. nitrosobenzene, 2-methyl-2-nitroso-
  • Heterocyclic aromatic compounds e. g. 10, 10-dimethyl-9 , 10-
  • scavengers for example a sterically hindered phenol with an
  • the solvent according to the invention can be any of the known
  • photoresist solvents or mixtures thereof which are suitable for photoresist solvents or mixtures thereof, which are suitable for photoresist solvents or mixtures thereof, which are suitable for photoresist solvents or mixtures thereof, which are suitable for photoresist solvents or mixtures thereof, which are suitable for photoresist solvents or mixtures thereof, which are suitable for photoresist solvents or mixtures thereof, which are suitable for photoresist solvents or mixtures thereof, which are suitable
  • preferred solvents are methoxypropylacetate, cyclopentanone, cyclohexanone, y-butyrolactone, ethyl lactate
  • Imagewise convertible film forming polymer 1 - 50 %
  • Photoacid generator 0.005 - 10 % preferably 0.02 - 1%
  • Radical scavenger 0.0001 - 5%, preferably 0.002 - 0.5 %
  • Solvent 50 - 99 %, most probable 88 - 98 %.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)

Abstract

Cette résine est capable de former des images lorsqu'on la soumet à un rayonnement possédant une longueur d'onde d'environ 157 nm, et elle comprend un polymère qui forme un film pouvant se convertir en images et est substitué par au moins un groupe chimique fonctionnel de déséquençage pouvant être clivé dans des conditions de cuisson catalysée par un acide, afin de former des groupes polaires dotant le polymère déséquencé de solubilité dans un révélateur alcalin aqueux. Au moins un composé générateur de photoacide libère un acide lors de son exposition à un rayonnement et catalyse le clivage des groupes de déséquençage. On utilise une dose efficace d'au moins un composé phagocyte de radicaux pour minimiser les réactions diminuant la solubilité du polymère déséquencé dans un révélateur alcalin aqueux, un solvant, au moins, étant également utilisé.
PCT/EP2001/000824 2000-01-25 2001-01-25 Resine amplifiee chimiquement et soumise a des ondes courtes WO2001055789A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US49131200A 2000-01-25 2000-01-25
US09/491,312 2000-01-25

Publications (2)

Publication Number Publication Date
WO2001055789A2 true WO2001055789A2 (fr) 2001-08-02
WO2001055789A3 WO2001055789A3 (fr) 2002-03-21

Family

ID=23951665

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2001/000824 WO2001055789A2 (fr) 2000-01-25 2001-01-25 Resine amplifiee chimiquement et soumise a des ondes courtes

Country Status (1)

Country Link
WO (1) WO2001055789A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10147953B4 (de) * 2001-09-28 2007-06-06 Infineon Technologies Ag CARL für Bioelektronik: Substratanbindung über isolierende Schicht

Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4800151A (en) * 1986-03-26 1989-01-24 Toray Industries, Inc. Radiation-sensitive positive resist comprising a fluorine-containing alpha-chloroacetate copolymer in the specification
EP0388343A2 (fr) * 1989-03-14 1990-09-19 International Business Machines Corporation Photoréserve avec amplification chimique
EP0445058A1 (fr) * 1990-03-01 1991-09-04 International Business Machines Corporation Composés pour augmenter la vitesse des photoréserves sensibilisées par un acide
EP0451741A2 (fr) * 1990-04-10 1991-10-16 E.I. Du Pont De Nemours And Company Plaque électrostatique photosensible positive
WO1994010608A1 (fr) * 1992-10-29 1994-05-11 International Business Machines Corporation Photoresist a amplification chimique
EP0795786A2 (fr) * 1996-03-11 1997-09-17 Fuji Photo Film Co., Ltd. Composition photosensible de type positif
EP0829766A2 (fr) * 1996-09-13 1998-03-18 Shipley Company LLC Nouveaux polymères et compositions de photoréserve
EP0877293A2 (fr) * 1997-05-09 1998-11-11 Fuji Photo Film Co., Ltd. Composition photosensible positive
EP0901043A1 (fr) * 1997-09-02 1999-03-10 JSR Corporation Composition photosensible à base de résine
EP0930541A1 (fr) * 1998-01-16 1999-07-21 JSR Corporation Composition sensible aux radiations à base de résine
EP0935172A1 (fr) * 1998-02-05 1999-08-11 Canon Kabushiki Kaisha Résine photosensible, réserve à base de cette résine photosensible, procédé d'exposition utilisant cette réserve et dispositif semi-conducteur obtenu par ce procédé d'exposition
US5952150A (en) * 1995-06-08 1999-09-14 Jsr Corporation Radiation sensitive resin composition
EP0959389A1 (fr) * 1998-05-19 1999-11-24 JSR Corporation Composé diazodisulfone et composition à base de résine sensible aux radiations
US6017675A (en) * 1995-10-31 2000-01-25 Ciba Specialty Chemials Corporation Oximesulfonic acid esters and the use thereof as latent sulfonic acids
EP1031878A1 (fr) * 1999-02-23 2000-08-30 Shipley Company LLC Nouveaux polymères et compositions pour photoréserves les comprenant
EP1035437A2 (fr) * 1999-03-12 2000-09-13 Lucent Technologies Inc. Matériau formant réserve sensible aux radiations et procédé de fabrication d'un dispositif utilisant ce matériau
US6136504A (en) * 1998-03-30 2000-10-24 Fuji Photo Film Co., Ltd. Positive-working photoresist composition
EP1048983A1 (fr) * 1999-04-28 2000-11-02 JSR Corporation Composition photosensible à base de résine
EP1085379A1 (fr) * 1999-09-17 2001-03-21 JSR Corporation Composition de résine photosensible
EP1091248A1 (fr) * 1999-10-06 2001-04-11 Fuji Photo Film Co., Ltd. Composition pour réserve de type positif
EP1099691A1 (fr) * 1999-11-09 2001-05-16 JSR Corporation Dérivés de la N-Sulfonyloxyimide et compositions sensibles aux radiations les utilisant
EP1126321A1 (fr) * 2000-02-10 2001-08-22 Shipley Company LLC Photoréserve de type positif contenant des polymères réticulés

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3954233B2 (ja) * 1998-03-30 2007-08-08 富士フイルム株式会社 ポジ型フォトレジスト組成物

Patent Citations (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4800151A (en) * 1986-03-26 1989-01-24 Toray Industries, Inc. Radiation-sensitive positive resist comprising a fluorine-containing alpha-chloroacetate copolymer in the specification
EP0388343A2 (fr) * 1989-03-14 1990-09-19 International Business Machines Corporation Photoréserve avec amplification chimique
EP0445058A1 (fr) * 1990-03-01 1991-09-04 International Business Machines Corporation Composés pour augmenter la vitesse des photoréserves sensibilisées par un acide
EP0451741A2 (fr) * 1990-04-10 1991-10-16 E.I. Du Pont De Nemours And Company Plaque électrostatique photosensible positive
WO1994010608A1 (fr) * 1992-10-29 1994-05-11 International Business Machines Corporation Photoresist a amplification chimique
US5952150A (en) * 1995-06-08 1999-09-14 Jsr Corporation Radiation sensitive resin composition
US6017675A (en) * 1995-10-31 2000-01-25 Ciba Specialty Chemials Corporation Oximesulfonic acid esters and the use thereof as latent sulfonic acids
EP0795786A2 (fr) * 1996-03-11 1997-09-17 Fuji Photo Film Co., Ltd. Composition photosensible de type positif
EP0829766A2 (fr) * 1996-09-13 1998-03-18 Shipley Company LLC Nouveaux polymères et compositions de photoréserve
EP0877293A2 (fr) * 1997-05-09 1998-11-11 Fuji Photo Film Co., Ltd. Composition photosensible positive
EP0901043A1 (fr) * 1997-09-02 1999-03-10 JSR Corporation Composition photosensible à base de résine
EP0930541A1 (fr) * 1998-01-16 1999-07-21 JSR Corporation Composition sensible aux radiations à base de résine
EP0935172A1 (fr) * 1998-02-05 1999-08-11 Canon Kabushiki Kaisha Résine photosensible, réserve à base de cette résine photosensible, procédé d'exposition utilisant cette réserve et dispositif semi-conducteur obtenu par ce procédé d'exposition
US6136504A (en) * 1998-03-30 2000-10-24 Fuji Photo Film Co., Ltd. Positive-working photoresist composition
EP0959389A1 (fr) * 1998-05-19 1999-11-24 JSR Corporation Composé diazodisulfone et composition à base de résine sensible aux radiations
EP1031878A1 (fr) * 1999-02-23 2000-08-30 Shipley Company LLC Nouveaux polymères et compositions pour photoréserves les comprenant
EP1035437A2 (fr) * 1999-03-12 2000-09-13 Lucent Technologies Inc. Matériau formant réserve sensible aux radiations et procédé de fabrication d'un dispositif utilisant ce matériau
EP1048983A1 (fr) * 1999-04-28 2000-11-02 JSR Corporation Composition photosensible à base de résine
EP1085379A1 (fr) * 1999-09-17 2001-03-21 JSR Corporation Composition de résine photosensible
EP1091248A1 (fr) * 1999-10-06 2001-04-11 Fuji Photo Film Co., Ltd. Composition pour réserve de type positif
EP1099691A1 (fr) * 1999-11-09 2001-05-16 JSR Corporation Dérivés de la N-Sulfonyloxyimide et compositions sensibles aux radiations les utilisant
EP1126321A1 (fr) * 2000-02-10 2001-08-22 Shipley Company LLC Photoréserve de type positif contenant des polymères réticulés

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10147953B4 (de) * 2001-09-28 2007-06-06 Infineon Technologies Ag CARL für Bioelektronik: Substratanbindung über isolierende Schicht

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WO2001055789A3 (fr) 2002-03-21

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