WO2022215456A1 - フォトレジスト用樹脂、フォトレジストおよび硬化物 - Google Patents

フォトレジスト用樹脂、フォトレジストおよび硬化物 Download PDF

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Publication number
WO2022215456A1
WO2022215456A1 PCT/JP2022/011547 JP2022011547W WO2022215456A1 WO 2022215456 A1 WO2022215456 A1 WO 2022215456A1 JP 2022011547 W JP2022011547 W JP 2022011547W WO 2022215456 A1 WO2022215456 A1 WO 2022215456A1
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WO
WIPO (PCT)
Prior art keywords
monomer
photoresist
meth
acrylate
mol
Prior art date
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.)
Ceased
Application number
PCT/JP2022/011547
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English (en)
French (fr)
Japanese (ja)
Inventor
彩花 山田
瑞貴 河野
敦 長澤
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.)
NOF Corp
Original Assignee
NOF 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.)
Filing date
Publication date
Application filed by NOF Corp filed Critical NOF Corp
Priority to JP2023512888A priority Critical patent/JPWO2022215456A1/ja
Priority to KR1020237035115A priority patent/KR20230167373A/ko
Priority to CN202280026236.5A priority patent/CN117222944A/zh
Publication of WO2022215456A1 publication Critical patent/WO2022215456A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • 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
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
    • C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
    • 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
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • 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
    • G03F7/20—Exposure; Apparatus therefor

Definitions

  • JP 2007-171311 A Japanese Unexamined Patent Application Publication No. 2008-3532 JP 2017-25236 A Japanese Patent Application Laid-Open No. 2016-170400
  • the amount of the DMC catalyst used is not particularly limited, but is 0.0001 to 0.1 mass per 100 parts by mass of the produced monomer (A) (that is, polyalkylene glycol mono(meth)acrylate). parts is preferred, and 0.001 to 0.05 parts by mass is more preferred.
  • the introduction of the DMC catalyst into the reaction system may be carried out all at once, or may be carried out sequentially in divided portions. After completion of the polymerization reaction, the DMC catalyst is removed. The catalyst can be removed by known methods such as filtration, centrifugation, and treatment with a synthetic adsorbent.
  • (meth)acrylic acid esters examples include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, pentyl (meth)acrylate, and (meth)acrylic ester.
  • organic peroxides include tert-butyl peroxy neodecanoate, tert-hexyl peroxypivalate, methyl ethyl ketone peroxide, cyclohexanone peroxide, 1,1-bis(tert-butylperoxy)-3, 3,5-trimethylcyclohexane, 2,2-bis(tert-butylperoxy)octane, n-butyl-4,4-bis(tert-butylperoxy)valerate, tert-butyl hydroperoxide, cumene hydroperoxide , 2,5-dimethylhexane-2,5-dihydroperoxide, di-tert-butyl peroxide, tert-butylcumyl peroxide, dicumyl peroxide, ⁇ , ⁇ '-bis(tert-butylperoxy- m-isopropyl)benzene, 2,5-dimethyl-2,5-di
  • azo compounds examples include 2,2'-azobisisobutyronitrile, 2,2'-azobis(2-methylbutyronitrile), 2,2'-azobis(4-methoxy-2,4-dimethyl valeronitrile), 2,2′-azobis(2,4-dimethylvaleronitrile), 1,1′-azobis(cyclohexane-1-carbonitrile), 2-(carbamoylazo)isobutyronitrile, 2-phenylazo- 4-methoxy-2,4-dimethyl-valeronitrile, 2,2′-azobis(2-methyl-N-phenylpropionamidine) dihydrochloride, 2,2′-azobis[N-(4-chlorophenyl)-2 -methylpropionamidine] dihydrochloride, 2,2'-azobis[N-hydroxyphenyl]-2-methylpropionamidine] dihydrochloride, 2,2'-azobis[2-methyl-N-(phenylmethyl)propion amidine] dihydrochlor
  • Glycine compounds include, for example, N-phenylglycine and the like.
  • acridine derivatives include 9-phenylacridine and the like.
  • oxime esters include 1-[4-(phenylthio)phenyl]-1,2-octanedione 2-(O-benzoyloxime) and the like.
  • mers glycine compounds, acridine derivatives, oxime esters, coumarin compounds, thioxanthone compounds, or acylphosphine oxide compounds, more preferably aromatic ketones, and particularly preferably 2-methyl-1-[4-(methylthio) phenyl]-2-morpholino-1-propanone.
  • (meth)acrylates neopentyl glycol di(meth)acrylate, 1,6-hexane glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, glycerin di(meth)acrylate, pentaerythritol di(meth)acrylate, At least one selected from the group consisting of pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate, more preferably di Pentaerythritol hexa(meth)acrylate, more preferably dipentaerythritol hexaacrylate.
  • the photoresist of the invention may contain components other than the resist resin, the photopolymerization initiator, the polyfunctional monomer, and the solvent as long as they do not impair the effects of the invention.
  • Other components may be used alone or in combination of two or more.
  • MMA monomer manufactured by Kuraray Co., Ltd.
  • Resin 6 A propylene glycol monomethyl ether solution of photoresist resin 6 (hereinafter sometimes referred to as "resin 6") was obtained in the same manner as in Example 1, except that the amount was changed to 24.0 g (0.098 mol).
  • BLEMMER PP-500 polypropylene glycol monomethacrylate
  • w b /w f is 1.39
  • BLEMMER PP-500 is a polyalkylene glycol mono(meth)acrylate that does not meet the requirements of formula (2) above.
  • Photoresist resin of the present invention By using the photoresist resin of the present invention, it is possible to suppress the generation of development residues, and to produce a photoresist that is excellent in the development residual film rate, residual film rate, and adhesion of the cured product. Photoresists of the invention are useful for the manufacture of electronic products such as televisions and smart phones.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
PCT/JP2022/011547 2021-04-06 2022-03-15 フォトレジスト用樹脂、フォトレジストおよび硬化物 Ceased WO2022215456A1 (ja)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2023512888A JPWO2022215456A1 (https=) 2021-04-06 2022-03-15
KR1020237035115A KR20230167373A (ko) 2021-04-06 2022-03-15 포토레지스트용 수지, 포토레지스트 및 경화물
CN202280026236.5A CN117222944A (zh) 2021-04-06 2022-03-15 光致抗蚀剂用树脂、光致抗蚀剂和固化物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2021-064980 2021-04-06
JP2021064980 2021-04-06

Publications (1)

Publication Number Publication Date
WO2022215456A1 true WO2022215456A1 (ja) 2022-10-13

Family

ID=83546058

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PCT/JP2022/011547 Ceased WO2022215456A1 (ja) 2021-04-06 2022-03-15 フォトレジスト用樹脂、フォトレジストおよび硬化物

Country Status (5)

Country Link
JP (1) JPWO2022215456A1 (https=)
KR (1) KR20230167373A (https=)
CN (1) CN117222944A (https=)
TW (1) TW202307569A (https=)
WO (1) WO2022215456A1 (https=)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10161310A (ja) * 1996-12-04 1998-06-19 Jsr Corp 感放射線性樹脂組成物
JP2009069814A (ja) * 2007-08-20 2009-04-02 Fujifilm Corp ポジ型感光性組成物及びそれを用いたパターン形成方法
JP2012163769A (ja) * 2011-02-07 2012-08-30 Toyo Ink Sc Holdings Co Ltd 感光性着色組成物及びそれを用いたカラーフィルタ
WO2017145771A1 (ja) * 2016-02-23 2017-08-31 Dic株式会社 ランダム共重合体、レジスト組成物、カラーフィルター及びランダム共重合体の製造方法
JP2018022153A (ja) * 2016-07-21 2018-02-08 富士フイルム株式会社 積層体及び液晶表示装置

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4753036B2 (ja) 2005-07-25 2011-08-17 日産化学工業株式会社 ポジ型感光性樹脂組成物及びそれから得られる硬化膜
JP2007171311A (ja) 2005-12-19 2007-07-05 Sekisui Chem Co Ltd レジスト材料、エッチングパターンの形成方法及び導電性パターンの形成方法
KR101612673B1 (ko) 2015-03-11 2016-04-14 동우 화인켐 주식회사 네가티브형 감광성 수지 조성물
JP2017025236A (ja) 2015-07-24 2017-02-02 明和化成株式会社 ノボラック型フェノール樹脂、その製造方法、及びそれを含むフォトレジスト組成物

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH10161310A (ja) * 1996-12-04 1998-06-19 Jsr Corp 感放射線性樹脂組成物
JP2009069814A (ja) * 2007-08-20 2009-04-02 Fujifilm Corp ポジ型感光性組成物及びそれを用いたパターン形成方法
JP2012163769A (ja) * 2011-02-07 2012-08-30 Toyo Ink Sc Holdings Co Ltd 感光性着色組成物及びそれを用いたカラーフィルタ
WO2017145771A1 (ja) * 2016-02-23 2017-08-31 Dic株式会社 ランダム共重合体、レジスト組成物、カラーフィルター及びランダム共重合体の製造方法
JP2018022153A (ja) * 2016-07-21 2018-02-08 富士フイルム株式会社 積層体及び液晶表示装置

Also Published As

Publication number Publication date
CN117222944A (zh) 2023-12-12
KR20230167373A (ko) 2023-12-08
TW202307569A (zh) 2023-02-16
JPWO2022215456A1 (https=) 2022-10-13

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