KR970015572A - 신규한 n-비닐락탐 유도체 및 그의 중합체 - Google Patents

신규한 n-비닐락탐 유도체 및 그의 중합체 Download PDF

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KR970015572A
KR970015572A KR1019950030063A KR19950030063A KR970015572A KR 970015572 A KR970015572 A KR 970015572A KR 1019950030063 A KR1019950030063 A KR 1019950030063A KR 19950030063 A KR19950030063 A KR 19950030063A KR 970015572 A KR970015572 A KR 970015572A
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carbon atoms
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hydrogen
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김진백
정민호
장경호
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윤덕용
한국과학기술원
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Priority to US08/713,085 priority patent/US5750680A/en
Priority to NL1004032A priority patent/NL1004032C2/nl
Priority to GB9619234A priority patent/GB2305175B/en
Priority to DE19637425A priority patent/DE19637425B4/de
Priority to TW085111278A priority patent/TW434460B/zh
Priority to CNB961199059A priority patent/CN1152859C/zh
Priority to FR9611264A priority patent/FR2738820B1/fr
Priority to JP8245089A priority patent/JP2929526B2/ja
Publication of KR970015572A publication Critical patent/KR970015572A/ko
Priority to US09/026,169 priority patent/US5955606A/en
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
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    • C07D207/26—2-Pyrrolidones
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    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings 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
    • C07D223/08—Oxygen atoms
    • C07D223/10—Oxygen atoms attached in position 2
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F26/06—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F26/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
    • C08F26/06—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a heterocyclic ring containing nitrogen
    • C08F26/10—N-Vinyl-pyrrolidone
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    • 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
    • G03F7/0387—Polyamides or polyimides
    • G—PHYSICS
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    • 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

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Abstract

본 발명은 비닐락탐의 3위치에 여러 종류의 보호기를 도입한 하기 일반식(Ⅰ)로 표시되는 신규한 N-비닐락탐 유도체, 그의 중합체 및 이들 중합체의 포토레지스트로서의 용도에 관한 것이다. 본 발명의 중합체는 초미세가공(microlithography)에서 원자외선 노광에 적합한 고감도, 고해상성의 화상을 형성할 수 있는 포토레지스트 재료로 사용될 수 있다. 또한 본 발명에 의해 제조된 포토레지스트는 초미세회로의 형성이 가능할 뿐만 아니라, 패턴형성의 공정도 획기적으로 개선할 수 있다.
상기 식에거, R1은 수소, 탄소수 1 내지 10개의 알킬기, 탄소수 6 내지 12개의 아릴기 또는 탄소수 3 내지 9개의 트리알킬실릴기이고; R2는 -OR′, -SO3R′, -CO2R′, -PO3R′, -SO2R′ 또는 -PO2R′(R′는 탄소수 1 내지 10개의 알킬기; 시클로알킬기; N, O, P, S의 헤테로원자를 포함한 시클로기; 또는, 탄소수 6 내지 12개의 아릴기)이며; R3는 수소, 탄소수 1 내지 10개의 알킬기, 탄소수 6 내지 12개의 아릴기, 탄소수 3 내지 9개의 트리알킬실릴기 또는 R2와 동일한 기이고; R4및 R5는 -OH, -OR(R은 탄소수 1 내지 10개의 알킬기 또는 탄소수 6 내지 12개의 아릴기) 또는 R1과 동일한 기이며, 및, m은 0 내지 10의 정수이다.

Description

신규한 N-비닐락탐 유도체 및 그의 중합체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (5)

  1. 하기 일반식(Ⅰ)로 표시되는 N-비닐락탐 유도체;
    상기 식에서, R1은 수소, 탄소수 1 내지 10개의 알킬기, 탄소수 6 내지 12개의 아릴기 또는 탄소수 3 내지 9개의 트리알킬실릴기이고; R2는 -OR′, -SO3R′, -CO2R′, -PO3R′, -SO2R′ 또는 -PO2R′(R′는 탄소수 1 내지 10개의 알킬기; 시클로알킬기; N, O, P, S의 헤테로원자를 포함한 시클로기; 또는, 탄소수 6 내지 12개의 아릴기)이며; R3는 수소, 탄소수 1 내지 10개의 알킬기, 탄소수 6 내지 12개의 아릴기, 탄소수 3 내지 9개의 트리알킬실릴기 또는 R2와 동일한 기이고; R4및 R5는 -OH, -OR(R은 탄소수 1 내지 10개의 알킬기 또는 탄소수 6 내지 12개의 아릴기) 또는 R1과 동일한 기이며, 및, m은 0 내지 10의 정수이다.
  2. 하기 일반식(Ⅱ)로 표시되는, 제1항의 N-비닐락탐 유도체(Ⅰ)의 단독중합체 또는 공중합체;
    상기 식에서, R1은 수소, 탄소수 1 내지 10개의 알킬기, 탄소수 6 내지 12개의 아릴기 또는 탄소수 3 내지 9개의 트리알킬실릴기이고; R2는 -OR′, -SO3R′, -CO2R′, -PO3R′, -SO2R′ 또는 -PO2R′(R′는 탄소수 1 내지 10개의 알킬기; 시클로알킬기; N, O, P, S의 헤테로원자를 포함한 시클로기; 또는, 탄소수 6 내지 12개의 아릴기)이며; R3는 수소, 탄소수 1 내지 10개의 알킬기, 탄소수 6 내지 12개의 아릴기, 탄소수 3 내지 9개의 트리알킬실릴기 또는 R2와 동일한 기이고; R4및 R5는 -OH, -OR(R은 탄소수 1 내지 10개의 알킬기 또는 탄소수 6 내지 12개의 아릴기) 또는 R1과 동일한 기이며, 및, m은 0 내지 10의 정수이고; 및 n은 10 내지 10000의 정수이다.
  3. 하기 일반식(Ⅲ)로 표시되는, 제1항의 N-비닐락탐 유도체(Ⅰ)와 스티렌계 유도체 또는 비닐아크릴레이트 계통 유도체으 공중합체;
    상기 식에서, R1은 수소, 탄소수 1 내지 10개의 알킬기, 탄소수 6 내지 12개의 아릴기 또는 탄소수 3 내지 9개의 트리알킬실릴기이고; R2는 -OR′, -SO3R′, -CO2R′, -PO3R′, -SO2R′ 또는 -PO2R′(R′는 탄소수 1 내지 10개의 알킬기; 시클로알킬기; N, O, P, S의 헤테로원자를 포함한 시클로기; 또는, 탄소수 6 내지 12개의 아릴기)이며; R3는 수소, 탄소수 1 내지 10개의 알킬기, 탄소수 6 내지 12개의 아릴기, 탄소수 3 내지 9개의 트리알킬실릴기 또는 R2와 동일한 기이고; R4및 R5는 -OH, -OR(R은 탄소수 1 내지 10개의 알킬기 또는 탄소수 6 내지 12개의 아릴기) 또는 R1과 동일한 기이며; R″는 탄소수 6 내지 20개의 아릴기 또는 아크릴레이트(-COOR″′) (R″′는 탄소수 1 내지 10개의 알킬기 또는 탄소수 6 내지 12개의 아릴기)이고; m은 0 내지 10의 정수이며; k는 0.5 내지 0.95의 물분률이고; 및 1은 0.05 내지 0.5의 물분률이다.
  4. 제2항의 중합체를 포함하는 화학증폭형 포토레지스트.
  5. 제3항의 중합체를 포함하는 화학증폭형 포토레지스트.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019950030063A 1995-09-14 1995-09-14 신규한 n-비닐락탐 유도체 및 그의 중합체 KR0178475B1 (ko)

Priority Applications (10)

Application Number Priority Date Filing Date Title
KR1019950030063A KR0178475B1 (ko) 1995-09-14 1995-09-14 신규한 n-비닐락탐 유도체 및 그의 중합체
US08/713,085 US5750680A (en) 1995-09-14 1996-09-12 N-vinyllactam derivatives and polymer thereof
GB9619234A GB2305175B (en) 1995-09-14 1996-09-13 N-vinyllactam derivatives and photoresist polymers thereof
DE19637425A DE19637425B4 (de) 1995-09-14 1996-09-13 Neue N-Vinyllactam-Derivate und deren Polymere
NL1004032A NL1004032C2 (nl) 1995-09-14 1996-09-13 Nieuwe N-vinyllactam derivaten en polymeren daarvan.
TW085111278A TW434460B (en) 1995-09-14 1996-09-14 Novel N-vinyllactam derivatives, polymer thereof, and photoresist composition containing the same
CNB961199059A CN1152859C (zh) 1995-09-14 1996-09-16 新型的n-乙烯基内酰胺衍生物和其聚合物
FR9611264A FR2738820B1 (fr) 1995-09-14 1996-09-16 Nouveaux derives de n-vinyllactame et leurs polymeres
JP8245089A JP2929526B2 (ja) 1995-09-14 1996-09-17 Ｎ−ビニルラクタム誘導体とその重合体、及びその重合体を含有するフォトレジスト
US09/026,169 US5955606A (en) 1995-09-14 1998-02-19 N-vinyllactam derivatives and polymer thereof

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KR1019950030063A KR0178475B1 (ko) 1995-09-14 1995-09-14 신규한 n-비닐락탐 유도체 및 그의 중합체

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KR970015572A true KR970015572A (ko) 1997-04-28
KR0178475B1 KR0178475B1 (ko) 1999-03-20

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DE (1) DE19637425B4 (ko)
FR (1) FR2738820B1 (ko)
GB (1) GB2305175B (ko)
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US6251560B1 (en) 2000-05-05 2001-06-26 International Business Machines Corporation Photoresist compositions with cyclic olefin polymers having lactone moiety
US6627391B1 (en) 2000-08-16 2003-09-30 International Business Machines Corporation Resist compositions containing lactone additives
US7138218B2 (en) * 2001-12-18 2006-11-21 Hynix Semiconductor Inc. Process for forming an ultra fine pattern using a bottom anti-reflective coating film containing an acid generator
US6756180B2 (en) * 2002-10-22 2004-06-29 International Business Machines Corporation Cyclic olefin-based resist compositions having improved image stability
DE10259815A1 (de) * 2002-12-19 2004-07-01 Basf Ag Polymere enthaltend Pyrrolidon-4-carbonsäuregruppen und deren Verwendung
US8119392B2 (en) * 2003-05-02 2012-02-21 The University Of North Carolina At Charlotte Biocompatible resists
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US7270937B2 (en) * 2003-10-17 2007-09-18 Hynix Semiconductor Inc. Over-coating composition for photoresist and process for forming photoresist pattern using the same
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JP4758679B2 (ja) * 2005-05-18 2011-08-31 パナソニック株式会社 レジスト材料及びそれを用いたパターン形成方法
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KR100861173B1 (ko) * 2006-12-01 2008-09-30 주식회사 하이닉스반도체 액침 노광 공정을 이용한 반도체 소자의 패턴 형성 방법
KR20080057562A (ko) * 2006-12-20 2008-06-25 주식회사 하이닉스반도체 반도체 소자의 미세 패턴 형성 방법
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JP5069494B2 (ja) * 2007-05-01 2012-11-07 ＡｚエレクトロニックマテリアルズＩｐ株式会社 微細化パターン形成用水溶性樹脂組成物およびこれを用いた微細パターン形成方法
KR100919564B1 (ko) * 2007-06-29 2009-10-01 주식회사 하이닉스반도체 반도체 소자의 미세 패턴 형성 방법
KR100876816B1 (ko) * 2007-06-29 2009-01-07 주식회사 하이닉스반도체 반도체 소자의 미세 패턴 형성 방법
WO2009152276A2 (en) 2008-06-10 2009-12-17 University Of North Carolina At Charlotte Photoacid generators and lithographic resists comprising the same
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KR101037528B1 (ko) 2008-10-16 2011-05-26 주식회사 하이닉스반도체 반도체 소자의 패턴 형성 방법
JP6182864B2 (ja) * 2012-01-17 2017-08-23 住友化学株式会社 レジストパターンの製造方法
JP6283477B2 (ja) * 2012-06-25 2018-02-21 ローム アンド ハース エレクトロニック マテリアルズ エルエルシーＲｏｈｍ ａｎｄ Ｈａａｓ Ｅｌｅｃｔｒｏｎｉｃ Ｍａｔｅｒｉａｌｓ ＬＬＣ アミド成分を含むフォトレジスト
JP2020536898A (ja) 2017-10-10 2020-12-17 バイオジェン インコーポレイテッド スピロ誘導体を調製するためのプロセス
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CN1153775A (zh) 1997-07-09
DE19637425B4 (de) 2006-04-13
FR2738820A1 (fr) 1997-03-21
JPH09216867A (ja) 1997-08-19
GB2305175A (en) 1997-04-02
TW434460B (en) 2001-05-16
FR2738820B1 (fr) 1998-09-11
DE19637425A1 (de) 1997-04-03
US5955606A (en) 1999-09-21
GB9619234D0 (en) 1996-10-23
NL1004032C2 (nl) 1997-05-21
NL1004032A1 (nl) 1997-03-20
CN1152859C (zh) 2004-06-09
US5750680A (en) 1998-05-12
GB2305175B (en) 1999-10-27
JP2929526B2 (ja) 1999-08-03

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