TW567402B - Negative resist composition for electron ray or X-ray - Google Patents

Negative resist composition for electron ray or X-ray Download PDF

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Publication number
TW567402B
TW567402B TW090116739A TW90116739A TW567402B TW 567402 B TW567402 B TW 567402B TW 090116739 A TW090116739 A TW 090116739A TW 90116739 A TW90116739 A TW 90116739A TW 567402 B TW567402 B TW 567402B
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TW
Taiwan
Prior art keywords
ray
electron
resist composition
group
negative resist
Prior art date
Application number
TW090116739A
Other languages
Chinese (zh)
Inventor
Toshiaki Aoso
Yutaka Adegawa
Morio Yagihara
Original Assignee
Fuji Photo Film Co Ltd
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Publication date
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Application granted granted Critical
Publication of TW567402B publication Critical patent/TW567402B/en

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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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
    • C07C229/18—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/643—2-Phenoxypyridines; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • 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
    • G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
    • 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
    • G03F7/038—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
    • 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
    • G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

Provided is a negative resist composition for electron ray or X-ray which may elevate the performance of finely processing semiconductor elements with an electron ray or X-ray and may satisfy the properties such as the sensitivity, resolution and resist profile with respect to the use of the electron ray or X-ray. A negative chemically amplified resist composition comprises a compound which generates a radical species upon irradiation with an electron ray or X-ray, a resin which is water-insoluble and alkali-soluble, and a specific monomer.

Description

567402 申請專利範圍567402 Patent Application Scope

2 R1 2) (a y 其中係表示氫原子、鹵素原子、氰基、或可具取代基 之烷基或鹵化烷基， ho〜Rn係表示氫原子、一般式（b)、（c)戥（d)之任一基、 可具取代基之縣、環絲、芳基、以基、或釀基， R13、R14係表示相同或不同的氫原子、_ _ _ ^ &基 '鹵素原 子、氰基或可具取代基之烷基、環烷基、燒基、芳院 基、或芳基，2 R1 2) (ay where represents a hydrogen atom, a halogen atom, a cyano group, or an alkyl group or a halogenated alkyl group which may have a substituent; ho ~ Rn represents a hydrogen atom, general formulae (b), (c) 戥 ( d) Any one of the groups, which may have a substituent, a ring, an aryl group, a phenyl group, or an aryl group, R13 and R14 represent the same or different hydrogen atoms, ___ ^ & groups, halogen atoms, Cyano or optionally substituted alkyl, cycloalkyl, alkyl, aryl, or aryl,

R 17 -15)c=c-c_ / II (16 〇(b)R 17 -15) c = c-c_ / II (16 〇 (b)

Ri: 18'Ri: 18 '

R 20R 20

R 一八2 一 21R one eight two one 21

R 22R 22

AA

R 19 3〜(CH)—(CH> n (c ) ^24 R25R 19 3 ~ (CH) — (CH > n (c) ^ 24 R25

Ris-O^C-C^C—A4— 〇 (d) 氰基、可 尺15〜I。、R24、Rw係表示氫原子、鹵素原子 具取代基之烷基或鹵化烷基， 567402 六、申請專利範圍 hi、R22係表示氫原子、羥基、可具取代基之烷基、烷氧 基、醯氧基，Ris-O ^ C-C ^ C—A4— 〇 (d) Cyano, 15 ~ I. R24 and Rw represent a hydrogen atom, a halogen atom having a substituted alkyl group or a halogenated alkyl group, 567402 VI. Patent application scope hi, R22 represents a hydrogen atom, a hydroxyl group, an alkyl group having a substituent, an alkoxy group, Methoxy,

Ru係表示氫原子、可具取代基之烷基、烷氧基、環烷 基、芳院基、或芳基， 、係表示單鍵、可具取代基之2價伸烷基、伸烯基、環 伸院基、或伸芳基、或-〇-、_S02-、-〇-c〇-R26-、-C0-0-R27-、-CO-N(R28)-R29-， 只26、R27、R29係表示相同或不同的單鍵、或具有醚構造、 醋構造、醯胺構造、胺基甲酸酯構造或脲素構造、且可 具取代基之2價伸烷基、伸烯基、環伸烷基、伸芳基， 只28係表示氫原子、可具取代基之烷基、環烷基、芳烷 基、或芳基， A2 係表示單鍵、-〇.r27- ' -N(r28)-R29-， A3係表示鍵、-S02•或可具伸烷基構造、或可具取代基之 伸芳基， A4係表示可具取代基之2價伸烷基、環伸烷基、伸芳 基、-0- 、 -S02- 、 -C0- 、 -C0-0-R21-， 义、7、2係表示0或1， ιώ、η係表示0或1以上之整數，· 惟一般式U2)中至少一個具有一般式（b)、（c)或（d)之基， 且R1Q〜R12中二個或R1Q〜R12中一個與Rn或R]4可鍵結 形成環。 567402 ^、申請專利範圍 4 .如申請專利範圍第1至3項中任一項之電子線或X 線負型抗蝕劑組成物，其中75keV以上加速電壓條 件下電子線照射。Ru represents a hydrogen atom, an alkyl group which may have a substituent, an alkoxy group, a cycloalkyl group, an aromatic group, or an aryl group, and represents a single bond, a divalent alkylene group which may have a substituent, and an alkenyl group. , Cyclosynthetic or aryl, or -〇-, _S02-, -〇-c〇-R26-, -C0-0-R27-, -CO-N (R28) -R29-, only 26, R27 and R29 represent the same or different single bond, or a divalent alkylene group or an alkenyl group having an ether structure, an acetic acid structure, a amine structure, a urethane structure, or a urea structure, and may have a substituent. , Cycloalkylene, and aryl, only 28 represents a hydrogen atom, an alkyl group which may have a substituent, a cycloalkyl, an aralkyl, or an aryl group, and A2 represents a single bond, -〇.r27- '- N (r28) -R29-, A3 represents a bond, -S02 • or an aryl group which may have an alkylene structure, or may have a substituent, and A4 represents a divalent alkyl group, which may have a substituent. Alkyl, arylene, -0-, -S02-, -C0-, -C0-0-R21-, meaning, 7, and 2 are 0 or 1, and ι and η are integers of 0 or more, · But at least one of the general formula U2) has the base of the general formula (b), (c) or (d), and two of R1Q ~ R12 or R1 One of Q to R12 may be bonded to Rn or R] 4 to form a ring. 567402 ^ Application scope 4. If the electron wire or X-ray negative resist composition according to any one of claims 1 to 3, the electron beam is irradiated under an acceleration voltage of 75keV or higher.

TW090116739A 2000-07-19 2001-07-09 Negative resist composition for electron ray or X-ray TW567402B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2000219253A JP4149122B2 (en) 2000-07-19 2000-07-19 Negative resist composition for electron beam or X-ray

Publications (1)

Publication Number Publication Date
TW567402B true TW567402B (en) 2003-12-21

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TW090116739A TW567402B (en) 2000-07-19 2001-07-09 Negative resist composition for electron ray or X-ray

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KR (1) KR100775453B1 (en)
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Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NO20031736D0 (en) * 2003-04-15 2003-04-15 Amersham Health As compounds
US9469941B2 (en) 2011-07-01 2016-10-18 Empire Technology Development Llc Paraben derivatives for preserving cellulosic materials

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08240911A (en) * 1995-03-02 1996-09-17 Japan Synthetic Rubber Co Ltd Radiation sensitive resin composition
JPH08272099A (en) * 1995-03-31 1996-10-18 Oki Electric Ind Co Ltd Radiation sensitive resin composition and pattern forming method using the composition
JP3633179B2 (en) * 1997-01-27 2005-03-30 Ｊｓｒ株式会社 Positive photoresist composition
JPH1149847A (en) * 1997-05-15 1999-02-23 Hitachi Ltd Photosensitive resin composition and insulation film and multilayer circuit board produced by using the composition
JPH1115154A (en) * 1997-06-20 1999-01-22 Chisso Corp Photosensitive resin composition and display device using the same
TWI250379B (en) * 1998-08-07 2006-03-01 Az Electronic Materials Japan Chemical amplified radiation-sensitive composition which contains onium salt and generator
JP2000147752A (en) * 1998-11-05 2000-05-26 Fuji Photo Film Co Ltd Negative resist composition
JP2000159828A (en) * 1998-11-30 2000-06-13 Nippon Shokubai Co Ltd Photosensitive resin composition, electron-beam-curable resin composition, and their cured items

Also Published As

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KR20020008077A (en) 2002-01-29
JP2002040656A (en) 2002-02-06
KR100775453B1 (en) 2007-11-12
JP4149122B2 (en) 2008-09-10

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