WO1994014858A1 - Reduction de la teneur en ions metalliques dans le polyhydroxystyrene et les photoresists - Google Patents

Reduction de la teneur en ions metalliques dans le polyhydroxystyrene et les photoresists Download PDF

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Publication number
WO1994014858A1
WO1994014858A1 PCT/US1993/012408 US9312408W WO9414858A1 WO 1994014858 A1 WO1994014858 A1 WO 1994014858A1 US 9312408 W US9312408 W US 9312408W WO 9414858 A1 WO9414858 A1 WO 9414858A1
Authority
WO
WIPO (PCT)
Prior art keywords
exchange resin
ion exchange
water
ppb
polyhydroxystyrene
Prior art date
Application number
PCT/US1993/012408
Other languages
English (en)
Inventor
M. Dalil Rahman
Michael T. Sheehan
Original Assignee
Hoechst Celanese Corporation
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 Hoechst Celanese Corporation filed Critical Hoechst Celanese Corporation
Publication of WO1994014858A1 publication Critical patent/WO1994014858A1/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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/04—Processes using organic exchangers
    • B01J39/05—Processes using organic exchangers in the strongly acidic form
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J39/00—Cation exchange; Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/08—Use of material as cation exchangers; Treatment of material for improving the cation exchange properties
    • B01J39/16—Organic material
    • B01J39/18—Macromolecular compounds
    • B01J39/20—Macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J41/00—Anion exchange; Use of material as anion exchangers; Treatment of material for improving the anion exchange properties
    • B01J41/04—Processes using organic exchangers
    • B01J41/07—Processes using organic exchangers in the weakly basic form
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J47/00—Ion-exchange processes in general; Apparatus therefor
    • B01J47/02—Column or bed processes
    • B01J47/026—Column or bed processes using columns or beds of different ion exchange materials in series

Definitions

  • the process of the subject invention provides water insoluble, aqueous alkali soluble polyhydroxystyrene obtained by polymerization of 4-hydroxystyrene, 3- hydroxystyrene, 2-hydroxystyrene, or copolymers of these monomers or the homopolymers and/or copolymers of the monomers of formula 1.
  • the polyhydroxystyrene obtained have very low levels of metal ions such as iron, sodium, potassium, calcium, magnesium, copper and zinc.
  • the total metal ion level is preferably less than 1 ppm, more preferably less than 500 ppb.
  • Sodium and iron are the most common metal ion contaminants and among the easiest to detect.
  • the level of these metal ions serves as an indicator of the level of other metal ions.
  • the level of sodium and iron ions are respectively, less than 100 ppb and 400 ppb, preferably less than 75 ppb and 300 ppb, more preferably less than 50 ppb and 200 ppb, even more preferably less than 30 ppb and 130 ppb and most preferably less than 10 ppb and 10 ppb.
  • PHS solution is added to water, preferably DI water, a precipitate is formed, the precipitate is filtered and dried to provide PHS having metal levels less than 500 ppb each, preferably 100 ppb, more preferably less than 50 ppb; f) providing an admixture of: D a photosensitive component in an amount sufficient to photosensitize the photoresist composition; 2) the water insoluble, aqueous alkali soluble PHS having a low level of chloride and sodium and iron ions and 3) a suitable solvent.
  • the photoresist composition is formed by providing an admixture of a photosensitizer, the subject water insoluble, aqueous alkali soluble PHS and a suitable solvent.
  • suitable solvents for such photo ⁇ resists and/or for PHS may include propylene glycol mono- alkyl ether, propylene glycol alkyl (e.g. methyl) ether acetate, ethyl-3-ethoxypropionate, ethyl lactate, mixtures of ethyl-3-ethoxypropionate and ethyl lactate, butyl acetate, xylene, diglyme, ethylene glycol monoethyl ether acetate.
  • the preferred solvents are propylene glycol methyl ether acetate (PGMEA) and ethyl-3- ethoxypropionate (EEP) .
  • Anti-striation agents may be used at up to about a five percent weight level, based on the combined weight of novolak and sensitizer.
  • Plasticizers which may be used include, for example, phosphoric acid tri- (beta- chloroethyl)-ester; stearic acid; dicamphor; polypropylene; acetal resins; phenoxy resins; and alkyl resins, at about one to ten percent weight levels, based on the combined weight of novolak and sensitizer.
  • the plasticizer additives improve the coating properties of the material and enable the application of a film that is smooth and of uniform thickness to the substrate.
  • the solvents may be present in the overall composition in an amount of up to 95% by weight of the solids in the composition. Solvents, of course are substantially removed after coating of the photoresist solution on a substrate and drying.
  • Non-ionic surfactants that may be used include, for example, nonylphenoxy poly(ethyleneoxy) ethanol; octylphenoxy ethanol at up to about 10% weight levels, based on the combined weight of novolak and sensitizer.
  • This temperature treatment is selected in order to reduce the concentration of residual solvents in the photo ⁇ resist, while not causing substantial thermal degradation of the photosensitizer.
  • this first temperature treatment is conducted until substantially all of the solvents have evaporated and a thin coating of photoresist composition, on , the order of one micron in thickness, remains on the substrate.
  • the temperature is from about 85°C to about 95°C.
  • the treatment is conducted until the rate of change of solvent removal becomes relatively insignificant.
  • the temperature and time selection depends on the photoresist properties desired by the user, as well as the equipment used and commercially desired coating times.
  • Developers may include aqueous solutions of ammonium or alkali metal hydroxides.
  • One preferred hydroxide is tetramethyl ammonium hydroxide.
  • the post-development heat treatment can comprise the oven baking of the coating and substrate below the coating's softening point.
  • the developed substrates may be treated with a buffered, hydrofluoric acid base etching solution.
  • the photoresist compositions of the present invention are resistant to acid-base etching solutions and provide effective protection for the unexposed photoresist-coating areas of the substrate.
  • Example 1 27 grams of dry AMBERLYST 15 ion exchange resin beads were placed in a conical flask and deionized water was added so that all of the resin beads were under water. The flask was sealed and allowed to stand overnight to swell the resin beads. The next morning the water was decanted, deionized water added to cover the resin beads and the flask was shaken slowly. The water was again decanted.
  • the rinsing with deionized water and decanting steps were repeated three more times.
  • the resulting slurry of ion exchange resin was poured into a 21.5 cm. long glass column having a diameter of 2 cm. and equipped with a porous disk and a stopcock. The resin was allowed to settle to the bottom and the column was back flushed with deionized water for 25 minutes. The resin was again allowed to settle to the bottom.
  • Example 2 50 grams of AMBERLYST 21 anionic ion exchange resin was placed in a conical flask and soaked in DI water overnight to allow swelling. The resulting slurry of ion exchange resin was poured into a glass column. The bed volume was measured to be 150 ml. The column was backflushed with DI water and allowed to resettle to pack properly. The resin bed was then washed with about 7 bed volumes of 4 wt.% aqueous NH 3 . This was followed by about 50 bed volumes of DI water until the resistivity of the water in was about equal to that of the water being taken out. The bed was then rinsed with 7 bed volumes of electronic grade methanol and allowed to sit overnight. The next day the bed was rinsed with an additional 3 bed volumes of electronic grade methanol. The anion exchange column was ready for use.
  • a cation exchange resin bed was made with 27 Kg of AMBERLYST 15 as exactly as described above for the anion exchange resin bed.
  • the bed volume was 11.7 gallons.
  • 10% H 2 S0 4 solution was made separately in three 55 gallon drums. 7 bed volumes of 10% H 2 S0 4 was pumped through the cation exchange resin bed to substantially remove metals. Then metal free nitrogen gas was passed through the resin bed. Enough bed volume of DI was then flushed through the resin bed until outlet resistivity was equal to inlet resistivity (16 m ⁇ ) .
  • Both the anion exchange resin bed and cation exchange resin bed were connected using an ion exchange resin loop.
  • the anion exchange resin bed was first in loop.
  • One drum of electronic grade methanol was pumped through both canisters at the rate of 1-2 gpm, to remove water from both the anion exchange and acidic ion exchange resin bed.
  • the dry PHS obtained by this process had a very low level of metal ions as shown in Table 3 below.
  • Example 4 was repeated except no anion exchange or acidic ion exchange resin bed was used to remove metals.
  • the PHS crude solution was precipitated in DI water exactly was described in Example 4 to 8 without being treated by anion exchange and cation exchange resin, and isolated and dried as exactly as described in Example 4 to 8.
  • the dry PHS obtained by this proces had a very high level of metal ions as shown in Table 4 below.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)

Abstract

L'invention concerne des procédés de production de polyhydroxystyrène aqueux soluble dans l'alcali et insoluble dans l'eau présentant une très faible teneur en chlorure et ions métalliques, à l'aide de résines échangeuses d'ions traitées anioniques et acides. L'invention se rapporte également à un procédé de production d'une composition à photorésist à très faible teneur en ions métalliques à partir dudit polyhydroxystyrène et à un procédé de production de dispositifs à semiconducteurs à l'aide desdites compositions à photorésist.
PCT/US1993/012408 1992-12-29 1993-12-20 Reduction de la teneur en ions metalliques dans le polyhydroxystyrene et les photoresists WO1994014858A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US99691792A 1992-12-29 1992-12-29
US07/996,917 1992-12-29

Publications (1)

Publication Number Publication Date
WO1994014858A1 true WO1994014858A1 (fr) 1994-07-07

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Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5476750A (en) * 1992-12-29 1995-12-19 Hoechst Celanese Corporation Metal ion reduction in the raw materials and using a Lewis base to control molecular weight of novolak resin to be used in positive photoresists
US5516886A (en) * 1992-07-10 1996-05-14 Hoechst Celanese Corporation Metal ion reduction in top anti-reflective coatings for photoresists
US5521052A (en) * 1994-12-30 1996-05-28 Hoechst Celanese Corporation Metal ion reduction in novolak resin using an ion exchange catalyst in a polar solvent and photoresists compositions therefrom
EP0718315A1 (fr) * 1994-12-20 1996-06-26 Ocg Microelectronic Materials, Inc. Procédé de préparation de résines phénoliques partiellement protégées
US5543263A (en) * 1992-03-06 1996-08-06 Hoechst Celanese Corporation Photoresist having a low level of metal ions
US5580949A (en) * 1991-12-18 1996-12-03 Hoechst Celanese Corporation Metal ion reduction in novolak resins and photoresists
US5580700A (en) * 1992-11-25 1996-12-03 Hoechst Celanese Corporation Metal ion reduction in bottom anti-reflective coatings for use in semiconductor device formation
US5594098A (en) * 1991-12-18 1997-01-14 Hoechst Celanese Corporation Metal ion reduction in novolak resins and photoresists
US5614352A (en) * 1994-12-30 1997-03-25 Hoechst Celanese Corporation Metal ion reduction in novolak resins solution in PGMEA by chelating ion exchange resin
WO1997011929A1 (fr) * 1995-09-28 1997-04-03 Clariant International, Ltd. 4,4'-(1-(4-(1-(4-hydroxyphenyl)-1-methylethyl)phenyl)ethyldiene)bisphenol (tppa) a faible niveau d'ions metalliques et compositions derivees pour photoresist
US5665517A (en) * 1996-01-11 1997-09-09 Hoechst Celanese Corporation Acidic ion exchange resin as a catalyst to synthesize a novolak resin and photoresist composition therefrom
US5686561A (en) * 1994-08-23 1997-11-11 Hoechst Celanese Corporation Metal ion reduction in novolak resin solution using an anion exchange resin
US5688893A (en) * 1992-12-29 1997-11-18 Hoechst Celanese Corporation Method of using a Lewis base to control molecular weight of novolak resins
US5750031A (en) * 1995-09-26 1998-05-12 Clariant Finance (Bvi) Limited Process for producing surfactant having a low metal ion level and developer produced therefrom
US5830990A (en) * 1992-07-10 1998-11-03 Clariant Finance (Bvi) Limited Low metals perfluorooctanoic acid and top anti-reflective coatings for photoresists
US5837417A (en) * 1994-12-30 1998-11-17 Clariant Finance (Bvi) Limited Quinone diazide compositions containing low metals p-cresol oligomers and process of producing the composition
US5936071A (en) * 1998-02-02 1999-08-10 Clariant Finance (Bvi) Limited Process for making a photoactive compound and photoresist therefrom
US5962183A (en) * 1995-11-27 1999-10-05 Clariant Finance (Bvi) Limited Metal ion reduction in photoresist compositions by chelating ion exchange resin
WO1999057163A1 (fr) * 1998-05-05 1999-11-11 Triquest, Lp Preparation constituee de co et terpolymeres de p-hydroxystyrene et d'acrylates d'alkyle
US6593431B2 (en) 2000-06-27 2003-07-15 Chemfirst Electronic Materials Lp Purification means
US6759483B2 (en) 1998-05-05 2004-07-06 Chemfirst Electronic Materials L.P. Preparation of homo-, co- and terpolymers of substituted styrenes
US6787611B2 (en) * 2000-06-27 2004-09-07 Chemfirst Electronic Materials L.P. Purification means
US6864324B2 (en) 2002-04-19 2005-03-08 Chem First Electronic Materials L.P. Anhydrous, liquid phase process for preparing hydroxyl containing polymers of enhanced purity
WO2007078445A1 (fr) * 2005-12-22 2007-07-12 Dupont Electronic Polymers L.P. Procede de preparation de compositions stables pour photoresist
US7834113B2 (en) 2003-05-08 2010-11-16 E. I. Du Pont De Nemours And Company Photoresist compositions and processes for preparing the same
US20100297551A1 (en) * 2009-05-19 2010-11-25 Tadashi Teranishi Process for producing photoresist polymeric compounds
US8021490B2 (en) 2007-01-04 2011-09-20 Eastman Chemical Company Substrate cleaning processes through the use of solvents and systems
JP2015214521A (ja) * 2014-05-13 2015-12-03 三菱レイヨン株式会社 化合物の精製方法、高分子化合物の製造方法、及びフォトリソグラフィー材料

Citations (4)

* Cited by examiner, † Cited by third party
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GB1509354A (en) * 1976-04-24 1978-05-04 Maruzen Oil Co Ltd Process for purifying halogenated alkenyl-phenol polymers
US4636540A (en) * 1985-07-08 1987-01-13 Atlantic Richfield Company Purification of polymer solutions
EP0408363A2 (fr) * 1989-07-13 1991-01-16 Fine Clay Co., Ltd. Méthode pour modifier des résines synthétiques et résines synthétiques ainsi modifiées
EP0544324A1 (fr) * 1991-11-28 1993-06-02 Maruzen Petrochemical Co., Ltd. Procédé d'élimination de métaux de polymères de vinylphénol

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1509354A (en) * 1976-04-24 1978-05-04 Maruzen Oil Co Ltd Process for purifying halogenated alkenyl-phenol polymers
US4636540A (en) * 1985-07-08 1987-01-13 Atlantic Richfield Company Purification of polymer solutions
EP0408363A2 (fr) * 1989-07-13 1991-01-16 Fine Clay Co., Ltd. Méthode pour modifier des résines synthétiques et résines synthétiques ainsi modifiées
EP0544324A1 (fr) * 1991-11-28 1993-06-02 Maruzen Petrochemical Co., Ltd. Procédé d'élimination de métaux de polymères de vinylphénol

Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5594098A (en) * 1991-12-18 1997-01-14 Hoechst Celanese Corporation Metal ion reduction in novolak resins and photoresists
US5580949A (en) * 1991-12-18 1996-12-03 Hoechst Celanese Corporation Metal ion reduction in novolak resins and photoresists
US5543263A (en) * 1992-03-06 1996-08-06 Hoechst Celanese Corporation Photoresist having a low level of metal ions
US5624789A (en) * 1992-07-10 1997-04-29 Hoechst Celanese Corporation Metal ion reduction in top anti-reflective coatings for photoresisis
US5516886A (en) * 1992-07-10 1996-05-14 Hoechst Celanese Corporation Metal ion reduction in top anti-reflective coatings for photoresists
US5830990A (en) * 1992-07-10 1998-11-03 Clariant Finance (Bvi) Limited Low metals perfluorooctanoic acid and top anti-reflective coatings for photoresists
US5580700A (en) * 1992-11-25 1996-12-03 Hoechst Celanese Corporation Metal ion reduction in bottom anti-reflective coatings for use in semiconductor device formation
US5476750A (en) * 1992-12-29 1995-12-19 Hoechst Celanese Corporation Metal ion reduction in the raw materials and using a Lewis base to control molecular weight of novolak resin to be used in positive photoresists
US5688893A (en) * 1992-12-29 1997-11-18 Hoechst Celanese Corporation Method of using a Lewis base to control molecular weight of novolak resins
US5686561A (en) * 1994-08-23 1997-11-11 Hoechst Celanese Corporation Metal ion reduction in novolak resin solution using an anion exchange resin
CN1074425C (zh) * 1994-08-23 2001-11-07 科莱恩金融(Bvi)有限公司 用阴离子交换树脂降低线型酚醛树脂溶液中的金属离子含量
US6043002A (en) * 1994-08-23 2000-03-28 Clariant Finance (Bvi) Limited Metal ion reduction in novolak resin solution using an anion exchange resin
EP0718315A1 (fr) * 1994-12-20 1996-06-26 Ocg Microelectronic Materials, Inc. Procédé de préparation de résines phénoliques partiellement protégées
US5663038A (en) * 1994-12-20 1997-09-02 Ocg Microelectronic Materials, Inc. Process for the preparation of partially protected phenolic resins
US5614352A (en) * 1994-12-30 1997-03-25 Hoechst Celanese Corporation Metal ion reduction in novolak resins solution in PGMEA by chelating ion exchange resin
US5837417A (en) * 1994-12-30 1998-11-17 Clariant Finance (Bvi) Limited Quinone diazide compositions containing low metals p-cresol oligomers and process of producing the composition
US5858627A (en) * 1994-12-30 1999-01-12 Clariant Finance (Bvi) Limited Image formation utilizing photosensitive compositions containing low metal content p-cresol oligomers
US5521052A (en) * 1994-12-30 1996-05-28 Hoechst Celanese Corporation Metal ion reduction in novolak resin using an ion exchange catalyst in a polar solvent and photoresists compositions therefrom
US5750031A (en) * 1995-09-26 1998-05-12 Clariant Finance (Bvi) Limited Process for producing surfactant having a low metal ion level and developer produced therefrom
US5656413A (en) * 1995-09-28 1997-08-12 Hoechst Celanese Corporation Low metal ion containing 4,4'-[1-[4-[1-(4-Hydroxyphenyl)-1-methylethyl]phenyl]ethylidene]bisphe nol and photoresist compositions therefrom
WO1997011929A1 (fr) * 1995-09-28 1997-04-03 Clariant International, Ltd. 4,4'-(1-(4-(1-(4-hydroxyphenyl)-1-methylethyl)phenyl)ethyldiene)bisphenol (tppa) a faible niveau d'ions metalliques et compositions derivees pour photoresist
US5962183A (en) * 1995-11-27 1999-10-05 Clariant Finance (Bvi) Limited Metal ion reduction in photoresist compositions by chelating ion exchange resin
US5665517A (en) * 1996-01-11 1997-09-09 Hoechst Celanese Corporation Acidic ion exchange resin as a catalyst to synthesize a novolak resin and photoresist composition therefrom
US5936071A (en) * 1998-02-02 1999-08-10 Clariant Finance (Bvi) Limited Process for making a photoactive compound and photoresist therefrom
US6048665A (en) * 1998-02-02 2000-04-11 Clariant Finance (Bvi) Limited Process for making a photoactive compound and photoresist therefrom
WO1999057163A1 (fr) * 1998-05-05 1999-11-11 Triquest, Lp Preparation constituee de co et terpolymeres de p-hydroxystyrene et d'acrylates d'alkyle
US6759483B2 (en) 1998-05-05 2004-07-06 Chemfirst Electronic Materials L.P. Preparation of homo-, co- and terpolymers of substituted styrenes
US6593431B2 (en) 2000-06-27 2003-07-15 Chemfirst Electronic Materials Lp Purification means
US6787611B2 (en) * 2000-06-27 2004-09-07 Chemfirst Electronic Materials L.P. Purification means
US6864324B2 (en) 2002-04-19 2005-03-08 Chem First Electronic Materials L.P. Anhydrous, liquid phase process for preparing hydroxyl containing polymers of enhanced purity
US7834113B2 (en) 2003-05-08 2010-11-16 E. I. Du Pont De Nemours And Company Photoresist compositions and processes for preparing the same
US7741429B2 (en) * 2005-12-22 2010-06-22 Dupont Electronic Polymers L.P. Process for preparing stable photoresist compositions
WO2007078445A1 (fr) * 2005-12-22 2007-07-12 Dupont Electronic Polymers L.P. Procede de preparation de compositions stables pour photoresist
US7862983B2 (en) * 2005-12-22 2011-01-04 Dupont Electronic Polymers L.P. Process for preparing stable photoresist compositions
US8207278B2 (en) 2005-12-22 2012-06-26 Dupont Electronic Polymers Lp Process for preparing stable photoresist compositions
US8580915B2 (en) * 2005-12-22 2013-11-12 E. I. Du Pont De Nemours And Company Process for preparing stable photoresist compositions
US8021490B2 (en) 2007-01-04 2011-09-20 Eastman Chemical Company Substrate cleaning processes through the use of solvents and systems
US20100297551A1 (en) * 2009-05-19 2010-11-25 Tadashi Teranishi Process for producing photoresist polymeric compounds
US8530134B2 (en) * 2009-05-19 2013-09-10 Daicel Chemical Industries, Ltd. Process for producing photoresist polymeric compounds
JP2015214521A (ja) * 2014-05-13 2015-12-03 三菱レイヨン株式会社 化合物の精製方法、高分子化合物の製造方法、及びフォトリソグラフィー材料

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