KR100408201B1 - Watersoluble photoresistor polymer having azido functional group at its side chain and preparation method thereof - Google Patents

Watersoluble photoresistor polymer having azido functional group at its side chain and preparation method thereof Download PDF

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KR100408201B1
KR100408201B1 KR10-2000-0020743A KR20000020743A KR100408201B1 KR 100408201 B1 KR100408201 B1 KR 100408201B1 KR 20000020743 A KR20000020743 A KR 20000020743A KR 100408201 B1 KR100408201 B1 KR 100408201B1
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acrylamide
azido
polymer
functional group
water
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KR20000037354A (en
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이동호
이준태
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일동화학 주식회사
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    • 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
    • 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
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/56—Acrylamide; Methacrylamide
    • 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
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • C08F220/60—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen
    • C08F220/603—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing nitrogen in addition to the carbonamido nitrogen and containing oxygen in addition to the carbonamido oxygen and nitrogen

Abstract

본 발명은 아크릴아미드를 주성분으로 하는 아크릴아미드＋디아세톤아크릴아미드＋비닐단량체의 삼원 공중합체에서 비닐단량체가 가진 작용기 X(예: 카르복실기, 아미노기)와 아지드 화합물의 작용기(예: 아미노기, 카르복실기등)가 반응하여 생성된 화학결합(예: 아미도(-CO-NH-))링키지를 통하여 아지도 기를 도입함으로써 종래에 별도의 첨가제로써 제공되는 비스아지드계에 비하여 감광효율이 높고 노광시간이 짧은 포토레지스트용 고분자를 제공한다.In the present invention, the functional group X (e.g., carboxyl group, amino group) possessed by the vinyl monomer and the functional group (e.g., amino group, carboxyl group, etc.) of the vinyl monomer in the terpolymer of acrylamide + diacetone acrylamide + vinyl monomer mainly composed of acrylamide ) By introducing azido groups through chemical bonds (e.g., amido (-CO-NH-)) linkages, which are formed by the reaction of Provided is a short photoresist polymer.

Description

아지도기를 고분자 측쇄에 가지는 수용성 포토레지스터 고분자 및 이의 제조방법{Watersoluble photoresistor polymer having azido functional group at its side chain and preparation method thereof}Water-soluble photoresistor polymer having azido group in the polymer side chain and its preparation method

본 발명은 아지도 관능기를 측쇄에 가지는 포토레지스터 수용성 고분자 및 이의 제조방법에 관한 것이다. 상세하게는 아지도기로 개질 된 아크릴 아미드를 주성분으로 하는 수용성 포토레지스터 고분자 및 이의 제조방법에 관한 것이다.The present invention relates to a photoresist water-soluble polymer having azido functional groups in the side chain and a method for producing the same. More particularly, the present invention relates to a water-soluble photoresist polymer mainly containing acrylamide modified with azido groups, and a method for preparing the same.

아지도기의 광반응은 산소 및 온도의 영향을 받고, 특히 산소에 의한 부반응의 발생(A.Reiser, Photoreactive polymers ; The science and technology of resist, John Wiley Sons, New York, 1989)으로 광반응 효율은 떨어지지만 광세기의 증가에 따라 상(image)을 얻는데 필요한 노광시간이 직선적인 관계를 가지지 않고 특히 광세기에서 상을 얻기 위한 노광시간의 범위가 넓은 특성을 가진다.(M,Akagi, S. Nonogaki, T. Kohashi, Y. Oba, and M, Oikawa, Polymer Engineering and Science, 17, 353-355(1997)).The photoreaction of azido groups is influenced by oxygen and temperature, and in particular, the side reactions caused by oxygen (A. Reiser, Photoreactive polymers; The science and technology of resist, John Wiley Sons, New York, 1989) Although the exposure time is decreased, the exposure time required for obtaining an image does not have a linear relationship, and the exposure time range for obtaining an image is particularly wide in light intensity (M, Akagi, S. Nonogaki). , T. Kohashi, Y. Oba, and M, Oikawa, Polymer Engineering and Science, 17, 353-355 (1997)).

이런 특징은 칼라브라운관의 제조에서 빨강, 녹색, 파랑의 세 가지 형광체를 형성할 자리를 만드는 블랙매트릭스(Black Matrix) 형성공정에서 마스크(mask)의교체 없이 하나의 마스크로 원하는 상을 얻을 수 있는 장점을 가진다. 현재까지 한 브라운관 제조의 블랙매트릭스 형성 공정에 사용되는 포토레지스터는 수용성 고분자와 아지도기를 양 말단에 가지는 수용성 비스아지드(bis-azide)를 혼합하여 제조하고 있다. 비스아지드는 양 말단의 아지도기가 각기 다른 고분자 사슬과 반응하여야 가교가 이루어지기 때문에 아지도기의 광반응 중에 가교반응을 유발하지 못하고 헛되이 소비되는 경우가 많다. 그래서 만족할 만한 상을 얻기 위해서는 과량의 비스아지드의 사용과 긴 노광시간이 필요하다.This feature allows the user to obtain the desired image with a single mask without replacing the mask in the process of forming a black matrix, which forms a place for forming three phosphors of red, green, and blue in the manufacture of color CRTs. Has The photoresist used in the black matrix forming process of the CRT is manufactured by mixing a water-soluble polymer and a water-soluble bis-azide having azido groups at both ends. Since bisazide is crosslinked only when the azido groups at both ends react with different polymer chains, bisazide is often consumed in vain without causing a crosslinking reaction during the photoreaction of azido groups. Therefore, in order to obtain a satisfactory image, the use of excess bis azide and a long exposure time are required.

본 발명은 광효율이 높고 짧은 노광시간에도 원하는 상을 제공하는데 적합한 아크릴 아미드를 주성분으로 하는 수용성 포토레지스터 고분자 및 이의 제조방법을 제공하기 위한 것이다.The present invention is to provide a water-soluble photoresist polymer containing a acrylamide as a main component suitable for providing a desired image even in a short exposure time with high light efficiency and a method for producing the same.

본 발명의 발명자들은 종래 기술에서 사용되는 수용성 비스아지드(bis-azide)대신에 아지도기를 아크릴아미드를 주성분으로 하는 고분자 측쇄에 도입하여 아지도기와 다른 고분자 사슬과 한번의 광반응에 의하여 가교가 되게 함으로써 광반응 효율을 획기적으로 개선할 수 있다는데 착안하여 본 발명을 완성하였다.The inventors of the present invention introduce the azido group into the polymer side chain containing acrylamide as a main component instead of the water-soluble bis-azide used in the prior art, so that crosslinking can be achieved by a single photoreaction with the azido group and other polymer chains. The present invention was completed with the focus on improving the photoreaction efficiency significantly.

본 발명에 의하여 단량체 몰 비율로 아크릴아미드 10∼30, 디아세톤 아크릴아미드 2∼10 및 비닐단량체 0.5∼5로 구성되고 화학결합으로 개질되어 아지도 관능기를 가지는 포토레지스터용 아크릴아미드 수용성 삼원공중합체가 제공된다.According to the present invention, an acrylamide water-soluble terpolymer for a photoresist composed of acrylamide 10-30, diacetone acrylamide 2-10 and vinyl monomer 0.5-5 in a monomer molar ratio and modified by chemical bonding to have an azido functional group Is provided.

여기서 비닐단량체는 카르 복실기 또는 아미노기등의 작용기를 가진 비닐단량체로서 예를 들면, 아크릴산이고 상기 개질된 화학결합은 예를 들면, 아미도(-CO-NH-)링키지이다.The vinyl monomer here is a vinyl monomer having a functional group such as a carboxyl group or an amino group, for example acrylic acid, and the modified chemical bond is, for example, amido (-CO-NH-) linkage.

또한 본 발명에 의하여Also by the present invention

1) 증류수에 단량체 몰비율로 10∼30 아크릴아미드, 2∼10의 디아세톤 아크릴아미드 및 0.5∼5의 작용기를 가지는 비닐단량체를 가하고 중합 개시제를 첨가하여 교반하면서 중합하는 단계;1) adding 10-30 acrylamide, 2-10 diacetone acrylamide, and a vinyl monomer having a functional group of 0.5-5 in a monomer molar ratio to distilled water, followed by polymerization by adding a polymerization initiator and stirring;

2) 1)단계에서 제조된 삼원중합체에 아지도 화합물을 첨가, 혼합하여 반응시킴으로써 아지도기를 중합체에 도입하는 단계; 및2) introducing an azido group into the polymer by adding, mixing and reacting an azido compound to the terpolymer prepared in step 1); And

3) 미반응된 아지도 화합물을 제거하는 단계로 이루어지는 화학결합으로 개질되어 아지도 관능기를 가지는 포토레지스터용 아크릴아미드 수용성 삼원공중합체의 제조방법이 제공된다.3) A method for producing an acrylamide water-soluble terpolymer for a photoresist having azido functional groups modified by a chemical bond consisting of removing unreacted azido compounds is provided.

상기 1)단계의 비닐단량체의 작용기는 예를 들면 카르복실기 또는 아미노기이다. 상기 비닐단량체는 바람직하게는 아크릴산이다.The functional group of the vinyl monomer of step 1) is, for example, a carboxyl group or an amino group. The vinyl monomer is preferably acrylic acid.

상기 2)단계의 아지도 화합물은 예를 들면 아지도 아닐린 아지도 카르복실산이고 상기 3)단계의 개질된 화학결합은 예를 들면 아미도 링키지(-CO-NH-)이다.The azido compound of step 2) is for example azido aniline azido carboxylic acid and the modified chemical bond of step 3) is for example amido linkage (-CO-NH-).

상기 단량체의 몰 비율에서 바람직하게는 아크릴아미드 15∼25, 디아세톤 아크릴아미드 4∼6 및 아크릴산 0.75∼2가 사용될 수 있다.In the molar ratio of the monomer, preferably acrylamide 15-25, diacetone acrylamide 4-6 and acrylic acid 0.75-2 can be used.

비닐단량체의 작용기는 아지드의 작용기와 반응하여 삼원중합체에 아지도기를 도입하게 해준다.The functional group of the vinyl monomer reacts with the functional group of the azide to introduce the azido group into the terpolymer.

이하 실시예에서 본 발명을 상세히 설명한다.In the following Examples the present invention will be described in detail.

(실시예)(Example)

중합체의 제조Preparation of Polymer

수용성 고분자에 카르복실산(carboxylic acid) 관능기를 도입하기 위하여 아크릴아미드(acrylamide), 디아세톤 아크릴아미드(diacetone acrylamide), 아크릴산(acrylic acid)을 삼원공중합체(ADAcT)를 제조한다. 500ml 삼구플라스크를 질소로 치환시킨 후 아크릴아미드 0.148 mole, 그리고 탈이온수(deionized water) 294ml를 넣고 30분간 교반하면서 반응응액 온도를 30。C로 맞춘다.In order to introduce a carboxylic acid functional group into the water-soluble polymer, acrylamide, diacetone acrylamide, and acrylic acid are prepared as terpolymers (ADAcT). The 500 ml three-necked flask was replaced with nitrogen, and 0.148 mole of acrylamide and 294 ml of deionized water were added thereto, followed by stirring for 30 minutes to adjust the reaction solution temperature to 30 ° C.

0.92mmol의 암모늄퍼설페이트(ammonium persulfate)와 0.11mmol의 소듐설피트(sodium sulfitle)를 산환·환원 개시제로 하여 중합 개시 후 24시간 중합한다.0.92 mmol of ammonium persulfate and 0.11 mmol of sodium sulfitle are used as an acid reduction / reduction initiator to polymerize for 24 hours after the start of polymerization.

아지도기의 도입Introduction of Azidogi

3.5 중량% ADAcT수용액 14.3g과 아지도아닐린 0.05g을 50ml 플라스크에 넣고, 상온에서 24시간 교반하였다. 반응시간동안 아지도기의 광반응을 방지하기 위해 빛을 차단한 상태를 유지하였다. 미반응의 아지도아닐린은 반응액을 아세톤에 침전, 여과 후 감압건조 과정을 통해 제거하였다.14.3 g of an aqueous 3.5 wt% ADAcT solution and 0.05 g of azido aniline were placed in a 50 ml flask and stirred at room temperature for 24 hours. During the reaction time, the light was blocked to prevent photoreaction of the azido group. The unreacted azidoaniline was removed by precipitation of the reaction solution in acetone, filtration and drying under reduced pressure.

포토레지스터의 감광성 조사Photoresist investigation of photoresist

자외선 분광석기를 이용하여 ADAcT에 도입된 아지도기의 함량을 구한 후, 아지도기 1mole에 대한 감광성을 수용성 고분자와 수용성 비스아지드(bis-azide:4,4'-diazidostilbene-2,2'-disulfonic acid disodium salt(DAS))를 혼합한 포토레지스터와 비교하여 그림 1에 나타내었다.After determining the content of azido groups introduced into ADAcT using UV spectroscopy, water-soluble polymers and water-soluble bisazides (bis-azide: 4,4'-diazidostilbene-2,2'-disulfonic) were detected. Acid disodium salt (DAS)) is shown in Figure 1.

감광성은 광에너지에 따라 가교되어 용매에 녹지 않고 남은 부분의 양을 조사하는 잔막수율법을 이용하였다.Photoresist was used as a residual film yield method that irradiates the amount of the remaining part without crosslinking according to the light energy insoluble in the solvent.

그림 1로부터 아지도기를 고분자 측쇄에 가지는 포토레지스터(ADAcT-Az)가 비스아지드와 수용성 고분자의 혼합으로 만들어지는 포토레지스터(ADAcT/DAS)보다 뛰어난 감광성을 가지는 것을 알 수 있었다.Figure 1 shows that the photoresist (ADAcT-Az) having azido groups in the polymer side chain has better photosensitivity than the photoresist (ADAcT / DAS) made of a mixture of bisazide and water-soluble polymer.

(그림 1. 아지도기(azido group)의 감광 효율 비교)(Figure 1. Comparison of photosensitive efficiency of azido group)

아지도 기를 고분자 측쇄에 도입하여 아지도기의 광반응이 고분자의 가교를 유발할 확율을 높임으로서 포토레지스터의 감도를 증가시키고 노광시간을 단축할 수 있다.By introducing an azido group into the polymer side chain, the photoreaction of the azido group can increase the probability of causing crosslinking of the polymer, thereby increasing the sensitivity of the photoresist and shortening the exposure time.

Claims (4)

단량체 몰비율로 아크릴아미드 10∼30, 디아세톤 아크릴아미드 2∼10 및 비닐단량체 0.5∼5로 구성되고 화학결합으로 개질되어 아지도 관능기를 가지는 포토레지스터용 아크릴아미드 수용성 삼원공중합체.An acrylamide water-soluble terpolymer for a photoresist composed of acrylamide 10-30, diacetone acrylamide 2-10, and vinyl monomer 0.5-5 in a monomer molar ratio and modified by chemical bonds to have an azido functional group. 제 1항에 있어서, 아크릴아미드, 디아세톤 아크릴아미드 및 비닐단량체의 몰비가 각각 15∼25, 4∼6 및 0.75∼2인 수용성 삼원공중합체.The water-soluble terpolymer according to claim 1, wherein the molar ratios of acrylamide, diacetone acrylamide and vinyl monomer are 15 to 25, 4 to 6 and 0.75 to 2, respectively. 제 1항 또는 제 2항에 있어서, 상기 비닐단량체는 아크릴산이고 상기 개질된 화학결합은 아미도(-CO-NH-)링키지인 삼원공중합체.3. The terpolymer of claim 1, wherein the vinyl monomer is acrylic acid and the modified chemical bond is an amido (—CO—NH—) linkage. 4. 증류수에 단량체 몰비율로 10∼30 아크릴아미드, 2∼10의 디아세톤 아크릴아미드 및 0.5∼5의 비닐단량체를 가하고 중합개시제를 첨가하여 교반하면서 중합하는 제1단계;A first step of adding 10-30 acrylamide, 2-10 diacetone acrylamide and 0.5-5 vinyl monomers in distilled water in a monomer molar ratio and adding a polymerization initiator, followed by polymerization while stirring; 상기 제1단계에서 제조된 삼원공중합체에 아지도 화합물을 첨가하여 혼합, 반응시킴으로써 아지도기를 중합체에 도입하는 제2단계; 및A second step of introducing an azido group into the polymer by adding, mixing and reacting an azido compound to the terpolymer prepared in the first step; And 미반응된 아지도 아닐린을 제거하는 제3단계로 이루어지는 화학결합으로 개질 되어 아지도 관능기를 가지는 포토레지스터용 아크릴아미드 수용성 삼원공중합체의 제조방법.A method for producing an acrylamide water-soluble terpolymer for a photoresist modified by a chemical bond consisting of a third step of removing unreacted azido aniline and having an azido functional group.
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