• Title/Summary/Keyword: Photoacid Generator

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Technology Trends for Photoresist and Research on Photo Acid Generator for Chemical Amplified Photoresist (포토 레지스트의 기술 동향과 화학 증폭형 포토레지스트에서의 광산 발생제의 연구)

  • Kim, Sung-Hoon;Kim, Sang-Tae
    • Journal of Integrative Natural Science
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    • v.2 no.4
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    • pp.252-264
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    • 2009
  • Lithographic data obtained from PHS(polyhydroxy styrene) having various functionalities were investigated by using a photoacid generator based on diazo and onium type. Chemically amplified photoresist based on the KrF type photoresist was developed by using a photoacid generator and multi-functional resin. Thermal stability for the photoacid generator showed that the increase of loading amount of photoacid generator resulted in the decrease of glass transintion temperature (Tg). The photoacid generators having methyl, ethyl, or propyl group in their cationic structure produced T-top structure in pattern profile due to the effect of acid diffusion during the generation of acid in the resist. The increase of carbon chain length in the anionic structure of photoacid generators resulted in lower pattern resolution due to the interruption of acid diffusion.

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Preparation and Characterization of p-Styrenesulfonates of Isopropylidene Dicyclohexanol as Acid Amplifiers to Enhance the Photosensitivity of Positive-Working Photoresists (포지티브 포토레지스트의 감도 증진을 위한 산 증식제로 이소프로필리덴 디시클로헥산올의 p-스티렌술폰산 에스테르의 합성 및 특성연구)

  • Lee, Eun-Ju;Hong, Kyong-Il;Lim, Kwon-Taek;Jeong, Yong-Seok;Hong, Sung-Su;Jeong, Yeon-Tae
    • Journal of the Korean Chemical Society
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    • v.46 no.5
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    • pp.437-471
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    • 2002
  • The photosensitivity enhancement of photoresist achieved by the addition of acid amplifiers stems from the autocatalytic decomposition of the acid amplifiers triggered by acidic species generated from a photoacid gen-erator. In this research we synthesized and evaluated 4-hydroxy-4'-p-styrenesulfonyloxy isopropylidene dicyclohex-ane(1), 4,4'-di-p-styrenesulfonyloxy isopropylidene dicyclohexane(2) and 4-p-styrenesulfonyloxy-4'-tosyloxy isopropylidene dicyclohexane(3) as novel acid amplifiers. These acid amplifiers(1-3) showed reasonable thermal stability for resist pro-cessing temperature. As estimated by the sensitivity curve, 1-3 were 2X-12X sensitive than poly(tert-butyl meth-acrylate) film in the presence of a photoacid generator and, therefore, provides practical applicability for photoimaging.

p-Toluenesulfonate Ester Derivatives of Benzendiol as Novel Acid Amplifiers (새로운 산증식제로 벤젠다이올의 p-톨루엔술폰산 에스터 유도체에 관한 연구)

  • Kang, Ji Eun;Hong, Kyoun Il;Lim, Kwon Taek;Jeong, Yeon Tae
    • Applied Chemistry for Engineering
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    • v.16 no.5
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    • pp.660-663
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    • 2005
  • Aiming the development of novel acid amplifiers, 2-hydroxyphenyl-4-methylbenzenesulfonate (1), 3-hydroxyphenyl-4-methylbenzene sulfonate (2), 4-hydroxyphenyl-4-methylbenzenesulfonate (3) were synthesized as the aromatic acid amplifiers with good thermal stability. They were autocatalytically generated p-toluenesulfonic acid in the presence of small amount of acid evolved from a photoacid generator. These aromatic sulfonates showed excellent thermal stability in PtBMA film and were proven to be the first aromatic acid amplifier to act as a photosensitivity enhancer. When these compounds were coupled with a chemically amplified photoresist system, photosensitivity was enhanced up to 3~6 folds.

Patterned Fluorescence Images with a t-Boc-Protected Coumarin Derivative

  • Min Sung-Jun;Park Bum Jun;Kim Jong-Man
    • Macromolecular Research
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    • v.12 no.6
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    • pp.615-617
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    • 2004
  • We have developed an efficient method for the generation of patterned fluorescence images using a protected precursor molecule. The t-Boc-protecting group of a coumarin derivative was readily removed from a polymer film upon irradiation with UV light in the presence of a photoacid generator to provide the original properties of the coumarin. Fine fluorescence patterns were obtained when using this photolithographic method.

Preparation and Characterization of Acid Amplifiers containing electron withdrawing group (전자끄는기를 갖는 산 증식제의 합성 및 특성 연구)

  • Lee, Eun-Ju;Jeong, Yeon-Tae
    • Journal of the Korean Graphic Arts Communication Society
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    • v.21 no.1
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    • pp.21-34
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    • 2003
  • Acid amplifiers derived from a certain class of sulfonates suffer from autocatalytic decomposition in the presence of a strong acid to give corresponding sulfonic acid, which catalyze the composition of the parent sulfonates, leading to the liberation of more of the same sulfonic acids in an exponential manner. In this research we synthesized and evaluated 4-hydroxy-4'-(2-trifluoromethyl)benzenesulfonyloxy isopropylidene dicyclohexane (1), 4,4'-di-(2-trifluoromethyl)benzenesulfonyloxy isopropylidene dicyclohexane (2), 4-hydroxy-4'-(3-trifluoromethyl)benzenesulfonyloxy isopropylidene dicyclohexane (3) and 4,4-di-(3-trifluoromethyl)benzenesulfonyloxy isopropylidene dicyclohexane (4) as novel acid amplifiers with electron withdrawing group. These acid amplifiers (1-4) showed reasonable thermal stability for resist processing temeprature and exhibited higher photosensitivity compared to poly(tert-butyl methacrylate) film without acid amplifiers. Application of acid amplifiers to photofunctional materials, including photoresists, are described as a consequence of the combination of the acid amplifiers with photoacid generator.

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Deep UV Photoresists;Dissolution Inhibitor

  • Shim, Sang-Yeon;Crivello, James V.
    • Journal of the Korean Applied Science and Technology
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    • v.17 no.3
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    • pp.188-191
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    • 2000
  • A new class of deep UV Photoresist based on the principles of chemical amplification was developed. This photoresist consists of three basic elements: a copolymer, blocked tetrabromobisphenol-A as a dissolution inhibitor and a photosensitive onium salt as a photoacid generator. On irradiation followed by a post exposure bake, tert-butoxycarbonyloxy phenyl group is converted to phenol group. Thus the initially base insoluble resin is converted under UV irradiation to a base soluble resin which may be preferentially removed by dissolution. This new photoresist display high sensitivity, 10 $mJ/cm^{2}$.

Synthesis and Characterization of Novel Acid Amplifiers with a Low Absorbance at 193 nm (193 nm에서 낮은 흡수도를 갖는 새로운 산 증식제의 합성 및 특성연구)

  • 소진호;정용석;최상준;정연태
    • Journal of the Korean Institute of Electrical and Electronic Material Engineers
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    • v.17 no.8
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    • pp.806-811
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    • 2004
  • 1-Hydroxy-4-(2-naphthalenesulfonyloxy) cyclohexane(1), 1,4-di-(2-naphthalenesulfonyloxy) cyclohexane(2), 1-hydroxy-4-(2-thiophenesulfonyloxy) cyclohexane(3), 1,4-di-(2-thiophenesulfonyloxy) cyclohexane(4) were synthesized and evaluated for their performance as novel acid amplifiers for 193 nm photoresists. These acid amplifiers(1-4) showed reasonable thermal stability at the usual resist-processing temperature, 9$0^{\circ}C$-12$0^{\circ}C$. And estimated by the sensitivity curve, (1)-(4) enhanced the sensitivity of poly(tert-butyl methacrylate) film by 1.2-1.4 times, compared to poly(tert-butyl methacrylate) film whithout acid amplifiers, in the presence of a photoacid generator.

Post Exposure Delay Effect Modeling and Simulation in Chemically Amplified Resists (화학증폭형 감광제의 노광후 지연 효과에 대한 모델링 및 시뮬레이션)

  • 김상곤;손동수;박흥진;손영수;오혜근
    • Proceedings of the Optical Society of Korea Conference
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    • 2001.02a
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    • pp.78-79
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    • 2001
  • 노광 후 지연(Post Exposure Delay: PED) 효과는 그림 1과 같이 노광 후 지연 시간에 따른 감광제의 Profile에 thinning, T-top, foot, undercut 를 보여주는 현상으로 화학 증폭형 감광제(Chemically Amplified Resist, CAR) 개발에 있어 PED의 안정성은 중요한 요소이다(1). 따라서 노광후 지연 효과에 대한 모델링은 연구와 개발을 위한 시뮬레이션 tool에 있어 매우 의미 있는 일이다. T-top 이나 undercut 를 형성하는 Surface inhibition layer(SIL) 은 노광 후 지연시 발생되는 environmental base contamination, acid evaporation 이 주요 원인이며 다른 원인으로는 감광제 속에서 acid migration, spin coating 동안에 photoacid generator (PAG)의 고갈, internal basic impurities 이며 그 외에 nonbsic atmospheric contamination, high power laser source의 영향 등이 있다. (중략)

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계산화학적 방법을 이용한 Triphenylsulfonium 양이온의 해리 반응 기작 연구

  • Hwang, In-Seung;Kim, Jong-Beom;Kim, Jae-Uk;Hong, Gwang-U;Kim, U-Yeon
    • Proceeding of EDISON Challenge
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    • 2016.03a
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    • pp.1-7
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    • 2016
  • Triphenylsulfonium 양이온(TPS)은 잘 알려진 광산 생성자(photoacid generator, PAG)중 하나로 양이온성 중합반응(cationic polymerization)의 개시제로 널리 사용됐으며, 유기발광다이오드의 활성층, 폴리머 발광다이오드의 전자주입층을 구성하는 재료로도 사용되고 있다. TPS는 200nm 주변의 빛을 흡수하면 탄소-황 결합이 끊어져 페닐 라디칼과 diphenylsulfonium 양이온 라디칼로 분해되는 것이 알려져 있다. 본 연구에서는 밀도범함수이론과 시간의존 밀도범함수이론을 이용 triphenylsulfonium 이온의 광학적 특성을 조사하였다. 가장 안정한 구조를 기준으로 자외선 흡광 스펙트럼을 계산하였고, 실험값에 잘 맞는 것을 확인하였다. TPS의 빛에 의한 해리 과정을 알아보기 위해 페닐-황 결합 길이를 변화시키며 TPS의 흡광 스펙트럼을 계산, 여기상태 포텐셜 에너지 곡선을 구할 수 있었다. 결합의 분해에 이용되는 상태들은 주로 점유 분자 오비탈에서 최저준위 비점유 분자 오비탈(LUMO)로 들뜨는 성분을 가지고 있었는데, 이는 LUMO가 반결합성 오비탈이기 때문이다.

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Poly[(1-methacryloyloxy-4-tosyloxycyclohexane)-co-(tert-butyl methacrylate)] as an acid amplifying photoresist (산 증식형 포토레지스트로 Poly($MTC_{10}-co-tBMA_{90}$)의 합성 및 특성 연구)

  • Kuen, Kyoung-A;Lee, Eun-Ju;Lim, Kwon-Taek;Jeong, Yong-Seok;Jeong, Yeon-Tae
    • Journal of the Korean Graphic Arts Communication Society
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    • v.20 no.2
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    • pp.131-140
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    • 2002
  • Chemically amplified deep UV(CA-DUV) resists are typically based on a combination of an acid labile polymer and a photoacid generator(PAG) but acid amplification type photoresist is formulated by addition of the acid amplifiers to chemically amplified resist system(CAPs). We developed acid amplifiers base on cyclohexanediol such as 1-methacryloyloxy-4-tosyloxy cyclohexane(MTC) and poly(MTC$_{10}$-co-tBMA$_{90}$)(P-1) to enhance photosensitivity. P-1 is a copolymer of tert-butyl methacrylate and MTC as a positive working photoresist based on polymeric acid amplifier in order to enhance photosensitivity and simplify the process of fomulating a photoresist. P-1 exhibited 2X higher photosensitivity compared with PtBMA. The acid amplifiers showed reasonable thermal stability for resist processing temperature and higher photosensitivity compared with chemically amplified resist.

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