KR101023429B1 - 푸리에 변환 근적외선 분광학을 이용한 감광성 수지 공중합체의 조성 분석방법 - Google Patents
푸리에 변환 근적외선 분광학을 이용한 감광성 수지 공중합체의 조성 분석방법 Download PDFInfo
- Publication number
- KR101023429B1 KR101023429B1 KR1020080132275A KR20080132275A KR101023429B1 KR 101023429 B1 KR101023429 B1 KR 101023429B1 KR 1020080132275 A KR1020080132275 A KR 1020080132275A KR 20080132275 A KR20080132275 A KR 20080132275A KR 101023429 B1 KR101023429 B1 KR 101023429B1
- Authority
- KR
- South Korea
- Prior art keywords
- photosensitive resin
- monomers
- resin copolymer
- composition
- nir
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- 239000011347 resin Substances 0.000 title claims abstract description 31
- 229920005989 resin Polymers 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims description 10
- 239000000178 monomer Substances 0.000 claims abstract description 51
- 238000004458 analytical method Methods 0.000 claims abstract description 36
- 238000004477 FT-NIR spectroscopy Methods 0.000 claims abstract description 31
- 238000011088 calibration curve Methods 0.000 claims abstract description 13
- 238000002156 mixing Methods 0.000 claims abstract description 6
- 229920001577 copolymer Polymers 0.000 claims description 12
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 229940116333 ethyl lactate Drugs 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- -1 haloalkyl Ester Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229920002120 photoresistant polymer Polymers 0.000 abstract description 11
- 238000004611 spectroscopical analysis Methods 0.000 abstract description 3
- 229920000642 polymer Polymers 0.000 description 7
- 238000007334 copolymerization reaction Methods 0.000 description 6
- OOIBFPKQHULHSQ-UHFFFAOYSA-N (3-hydroxy-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC2(O)CC1(OC(=O)C(=C)C)C3 OOIBFPKQHULHSQ-UHFFFAOYSA-N 0.000 description 5
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- 241001446467 Mama Species 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000004065 semiconductor Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- AATKCDPVYREEEG-UHFFFAOYSA-N (2-methyl-1-adamantyl) 2-methylprop-2-enoate Chemical compound C1C(C2)CC3CC1C(C)C2(OC(=O)C(C)=C)C3 AATKCDPVYREEEG-UHFFFAOYSA-N 0.000 description 1
- QSUJHKWXLIQKEY-UHFFFAOYSA-N (2-oxooxolan-3-yl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCOC1=O QSUJHKWXLIQKEY-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Images
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01J—MEASUREMENT OF INTENSITY, VELOCITY, SPECTRAL CONTENT, POLARISATION, PHASE OR PULSE CHARACTERISTICS OF INFRARED, VISIBLE OR ULTRAVIOLET LIGHT; COLORIMETRY; RADIATION PYROMETRY
- G01J3/00—Spectrometry; Spectrophotometry; Monochromators; Measuring colours
- G01J3/12—Generating the spectrum; Monochromators
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/35—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using infrared light
- G01N21/359—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using infrared light using near infrared light
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/17—Systems in which incident light is modified in accordance with the properties of the material investigated
- G01N21/25—Colour; Spectral properties, i.e. comparison of effect of material on the light at two or more different wavelengths or wavelength bands
- G01N21/31—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry
- G01N21/35—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using infrared light
- G01N2021/3595—Investigating relative effect of material at wavelengths characteristic of specific elements or molecules, e.g. atomic absorption spectrometry using infrared light using FTIR
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Investigating Or Analysing Materials By Optical Means (AREA)
Abstract
Description
Claims (7)
- 2종 이상의 모노머를 여러 가지 비율로 혼합하여 얻은 혼합물로부터 푸리에 변환 근적외선 분광학(FT-NIR) 분석을 통하여 상기 모노머 각각에 대한 검량선을 작성한 후, 상기 2종 이상의 모노머로 이루어진 분석하고자 하는 감광성 수지 공중합체를 FT-NIR 분석하여 얻어진 값을 상기 검량선에 대입하여 공중합체의 조성을 산출해 내는 것을 포함하며, 상기 감광성 수지 공중합체가 하기 화학식 1 내지 4로 표시되는 반복단위를 2종 이상 포함하는 것을 특징으로 하는 감광성 수지 공중합체의 조성 분석방법:[화학식 1][화학식 2][화학식 3][화학식 4]상기 식에서,R1은 수소, 할로겐, C1-6 알킬 또는 C1-6 할로알킬이고,R2는 C1-6 알킬, 할로겐 또는 하이드록시로 치환되거나 비치환된, C2-15 지방족 탄화수소기, C6-18 방향족 탄화수소기, 락토닐 또는 부티로락토닐이고,R3는 C2-15 알킬, C2-15 할로알킬, C2-15 알킬카보닐 또는 실릴이고,R4는 C2-15 알킬, C2-15 할로알킬, C2-15 알킬카보닐, C2-15 알콕시, C2-15 할로알콕시, C2-15 알킬에스테르, C2-15 할로알킬에스테르 또는 실릴이다.
- 삭제
- 제 1 항에 있어서,상기 감광성 수지 공중합체가 아크릴레이트계 또는 메타크릴레이트계 공중합체인 것을 특징으로 하는, 감광성 수지 공중합체의 조성 분석방법.
- 제 1 항에 있어서,상기 2종 이상의 모노머의 혼합물 및 상기 감광성 수지 공중합체를 각각 유기용매에 용해시킨 후 각각의 용액에 대해서 FT-NIR 분석을 수행하는 것을 특징으로 하는, 감광성 수지 공중합체의 조성 분석방법.
- 제 4 항에 있어서,상기 유기용매가 테트라하이드로푸란, 프로필렌글리콜 모노메틸 에테르 아세테이트, 에틸 락테이트, 메틸에틸케톤 및 이들의 혼합물로 이루어진 군으로부터 선택되는 것을 특징으로 하는, 감광성 수지 공중합체의 조성 분석방법.
- 제 4 항에 있어서,상기 용액이 10 내지 30 중량%의 농도를 갖는 것을 특징으로 하는, 감광성 수지 공중합체의 조성 분석방법.
- 삭제
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020080132275A KR101023429B1 (ko) | 2008-12-23 | 2008-12-23 | 푸리에 변환 근적외선 분광학을 이용한 감광성 수지 공중합체의 조성 분석방법 |
JP2009028846A JP2010151779A (ja) | 2008-12-23 | 2009-02-10 | フーリエ変換近赤外線分光学を用いた感光性樹脂コポリマーの組成分析方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1020080132275A KR101023429B1 (ko) | 2008-12-23 | 2008-12-23 | 푸리에 변환 근적외선 분광학을 이용한 감광성 수지 공중합체의 조성 분석방법 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20100073562A KR20100073562A (ko) | 2010-07-01 |
KR101023429B1 true KR101023429B1 (ko) | 2011-03-25 |
Family
ID=42571018
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020080132275A KR101023429B1 (ko) | 2008-12-23 | 2008-12-23 | 푸리에 변환 근적외선 분광학을 이용한 감광성 수지 공중합체의 조성 분석방법 |
Country Status (2)
Country | Link |
---|---|
JP (1) | JP2010151779A (ko) |
KR (1) | KR101023429B1 (ko) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101970161B1 (ko) * | 2017-03-24 | 2019-04-19 | 주식회사 케이씨씨 | 수지의 정량분석 방법 및 이로 분석된 방오 수지 |
JP7110765B2 (ja) * | 2018-06-29 | 2022-08-02 | 株式会社島津製作所 | 4種の物質の含有率を測定する測定方法、測定処理プログラムおよび測定装置 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR920704122A (ko) * | 1989-11-07 | 1992-12-19 | 원본미기재 | 복합물에서 수지의 경화도측정 방법 및 복합물 제조방법 |
JPH07301599A (ja) * | 1990-04-09 | 1995-11-14 | Ashland Oil Inc | 近赤外分光学分析法による炭化水素を分析するための方法 |
KR20040026868A (ko) * | 2002-09-26 | 2004-04-01 | 현대자동차주식회사 | Abs계 수지의 정량 분석방법 |
KR20050091288A (ko) * | 2004-03-11 | 2005-09-15 | 주식회사 동진쎄미켐 | 근적외선 분광기를 이용한 리쏘그래피 공정용 조성물의실시간 제어 시스템 및 제어 방법 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010513669A (ja) * | 2006-12-19 | 2010-04-30 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 均一組成コポリマー用のセミバッチ共重合方法 |
-
2008
- 2008-12-23 KR KR1020080132275A patent/KR101023429B1/ko active IP Right Grant
-
2009
- 2009-02-10 JP JP2009028846A patent/JP2010151779A/ja active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR920704122A (ko) * | 1989-11-07 | 1992-12-19 | 원본미기재 | 복합물에서 수지의 경화도측정 방법 및 복합물 제조방법 |
JPH07301599A (ja) * | 1990-04-09 | 1995-11-14 | Ashland Oil Inc | 近赤外分光学分析法による炭化水素を分析するための方法 |
KR20040026868A (ko) * | 2002-09-26 | 2004-04-01 | 현대자동차주식회사 | Abs계 수지의 정량 분석방법 |
KR20050091288A (ko) * | 2004-03-11 | 2005-09-15 | 주식회사 동진쎄미켐 | 근적외선 분광기를 이용한 리쏘그래피 공정용 조성물의실시간 제어 시스템 및 제어 방법 |
Also Published As
Publication number | Publication date |
---|---|
JP2010151779A (ja) | 2010-07-08 |
KR20100073562A (ko) | 2010-07-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Musto et al. | A study by Raman, near-infrared and dynamic-mechanical spectroscopies on the curing behaviour, molecular structure and viscoelastic properties of epoxy/anhydride networks | |
Jin et al. | Methacryloyl-functional benzoxazine: photopolymerization and thermally activated polymerization | |
Huang et al. | Studying the miscibility and thermal behavior of polybenzoxazine/poly (ε-caprolactone) blends using DSC, DMA, and solid state 13C NMR spectroscopy | |
Twum et al. | Characterization of the chain-ends and branching structures in polyvinylidene fluoride with multidimensional NMR | |
Abd El-Kader et al. | Spectroscopic behavior of poly (vinyl alcohol) films with different molecular weights | |
TW201114782A (en) | Method for producing polymer, polymer for lithography, composition for resist and method for producing substrate | |
Cockburn et al. | Free Radical Copolymerization Kinetics of γ-Methyl-α-methylene-γ-butyrolactone (MeMBL) | |
Jager et al. | Photopolymerization of polyfunctional acrylates and methacrylate mixtures: characterization of polymeric networks by a combination of fluorescence spectroscopy and solid state nuclear magnetic resonance | |
Darvishi et al. | Copolymers of glycidyl methacrylate and octadecyl acrylate: synthesis, characterization, swelling properties, and reactivity ratios | |
Chakrapani et al. | Low-field 1 H-NMR spectroscopy for compositional analysis of multicomponent polymer systems | |
Wang et al. | PLP/SEC/NMR study of free radical copolymerization of styrene and glycidyl methacrylate | |
KR101023429B1 (ko) | 푸리에 변환 근적외선 분광학을 이용한 감광성 수지 공중합체의 조성 분석방법 | |
Venkataraman et al. | ATRP from an amino acid-based initiator: A facile approach for α-functionalized polymers | |
Klok et al. | Fluorescent star‐shaped polystyrenes:“core‐first” synthesis from perylene‐based ATRP initiators and dynamic mechanical solid‐state properties | |
Al-Harthi et al. | Atom transfer radical polymerization (ATRP) of styrene and acrylonitrile with monofunctional and bifunctional initiators | |
Ito et al. | Radical copolymerization of 2‐trifluoromethylacrylic monomers. I. Kinetics of their copolymerization with norbornenes and vinyl ethers as studied by in situ 1H NMR analysis | |
JP5531563B2 (ja) | 共重合体の定量方法 | |
Lou et al. | Copolymers of methyl methacrylate with N‐trifluorophenyl maleimides: High glass transition temperature and low birefringence polymers | |
Hasanzadeh et al. | A reactive copolymer based on Glycidylmethacrylate and Maleic Anhydride: 1-synthesis, characterization and monomer reactivity ratios | |
Zhou et al. | Effects of Monomer Functionality and Hydrogen Bonding on the Polymerization Kinetics and Properties of Thiol− Ene Networks | |
Lou et al. | A novel copolymer of methyl methacrylate with N-pentafluorophenyl maleimide: High glass transition temperature and highly transparent polymer | |
Liu et al. | Unusual effect of molecular weight and concentration on thermoresponsive behaviors of well‐defined water‐soluble semirigid polymers | |
Li et al. | Use of 1H/13C/19F Triple Resonance 3D-NMR to Characterize the Stereosequences in Poly (vinyl fluoride) | |
Soykan et al. | Novel copolymers of N-(4-bromophenyl)-2-methacrylamide with glycidyl methacrylate: Synthesis, characterization, monomer reactivity ratios and thermal properties | |
Mathias et al. | Synthesis and wide-line NMR studies of α-deuterated polyacrylates and polyacrylonitrile |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A201 | Request for examination | ||
E902 | Notification of reason for refusal | ||
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
FPAY | Annual fee payment |
Payment date: 20140217 Year of fee payment: 4 |
|
FPAY | Annual fee payment |
Payment date: 20150223 Year of fee payment: 5 |
|
FPAY | Annual fee payment |
Payment date: 20160222 Year of fee payment: 6 |
|
FPAY | Annual fee payment |
Payment date: 20170208 Year of fee payment: 7 |
|
FPAY | Annual fee payment |
Payment date: 20180226 Year of fee payment: 8 |
|
FPAY | Annual fee payment |
Payment date: 20190213 Year of fee payment: 9 |
|
FPAY | Annual fee payment |
Payment date: 20200221 Year of fee payment: 10 |