PS 판용 1,2-Naphthoquinone-(2)diazide-5-sulfonic Acid Ester Derivatives 의 합성 및 응용

구양서; 명영찬; 안종일; 김선호

Journal of the Korean Industrial and Engineering Chemistry, Vol.10, No.8, 1169-1174, December, 1999

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PS 판용 1,2-Naphthoquinone-(2)diazide-5-sulfonic Acid Ester Derivatives 의 합성 및 응용

Studies on 1,2-Naphthoquinone-(2)diazide-5-sulfonic Acid Ester Derivatives for Pre-sensitized Offset Plates

구양서, 명영찬, 안종일, 김선호

초록

본 연구에서는 sodium 2-diazo-1-naphthoquinone-5-sulfonate를 chlorination하여 2-diazo-naphthoquinone-5-sulfonyl chloride(NQD-Cl)를 합성하였다. NQD-Cl을 여러 종류의 hydroxybenzophenone 유도체와 esterification하여 hydroxy group이 2-diazo-naphthoquinone-5-sulfonyl(NQD) group으로 치환된 여러 종류의 1,2-naphthoquinone-(1,2)-diazide-5-sulfonic acid esters(NQD0ester) 유도체를 합성하였다. NQD-ester 유도체의 용해도를 증가시키기 위해 methoxy group이 도입된 유도체와 이와 비교를 위해 hydroxy group만을 가지는 benzophenone 유도체를 사용하여 비교하였다. 각각의 NQD-ester 유도체의 용해특성을 조사하였으며, novolac수지와 혼용(formulation)하여 감광액을 제조하여 알루미늄판에 도포, 건조하여 PS판을 제조하였다. PS판의 감광특성과 광퇴색도와 화상형성에 적합한 노광시간을 조사하였으며, 상대감도를 gray scale(GS)법으로 조사하였다. 치환된 NQD group 의 수에 따라 GS법에 의한 상대감도가 다르게 나타나는 것을 알 수 있었다. Methoxy group이 도입된 NQD-ester유도체는 좋은 용해특성을 보여주었으며 시판되는 PS판과 동일한 노광조건에서 비교해 본 결과 보다 우수한 감도를 보였다.

2-Diazo-1-naphthoquinone-5-sulfonyl chloride(NQD-Cl) was synthesized from sodium 2-diazo-naphthoquinone-5-sulfonate by chlorination. NQD-Cl was esterified with hydroxybenzophenones to give several 1,2-naphthoquinone-(2)-diazide-5-sulfonic acid ester derivatives(NQD-esters). We have compared benzophenone derivatives with methoxy group to benzophenone derivatives with hydroxy group. Solubility of each NQD-ester was studied. Each of NQD-esters was formulated with novolac base resin and PS plates were manufactured. Photosensitivity, bleachability, compatible exposed time and relative sensitivity were determined by UV spectrophotometry, imaged by UV lithographic techniques, and the gray scale method. According to the number of substituted NQD group, it showed that relative sensitivity was different from gray scale method. NQD-esters with methoxy group showed a good solubility and higher sensitivity than commercial PS ones.

Keywords:1;2-naphthoquinone-(2)diazide-5-sulfonic acid esters;methoxy group;solubility;PS plates;photosensitivity

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[1] 박이순, 김성주, 화학세계, 34, 646 (1994)

[2] 유희열, 반도체, 12, 65 (1996)

[3] Joo SY, Hong SI, J. Korean Ind. Eng. Chem., 1(2), 116 (1990)

[4] 권태선, 황석환, 김성훈, 한국인쇄학회지, 12, 35 (1994)

[5] Reiser A, "Photoreactive Polymers," 178-225, John Wiley & Sons, Inc. New York (1989)

[6] Geishina AD, Vannikov AV, J. Photochem. Photobiol., 114, 159 (1998)

[7] 電氣化學, 64 (1996)

[8] Willson G, Miller R, Polym. Eng. Sci., 23, 1004 (1983)

[9] Shih HY, Reiser A, Macromolecules, 29(6), 2082 (1996)

[10] Mochizuki A, Teranishi T, Ueda M, Matsushita K, Polymer, 36(11), 2153 (1995)

[11] Reiser A, J. Imaging Sci. Technol., 42, 15 (1998)

[12] Neugebaure W, U.S. Patent, 3,201,239 (1960)

[13] 안광덕, 반도체, 2, 31 (1996)