KR930009814B1 - Tert-butoxycarbonyl - Google Patents

Tert-butoxycarbonyl Download PDF

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KR930009814B1
KR930009814B1 KR1019910010273A KR910010273A KR930009814B1 KR 930009814 B1 KR930009814 B1 KR 930009814B1 KR 1019910010273 A KR1019910010273 A KR 1019910010273A KR 910010273 A KR910010273 A KR 910010273A KR 930009814 B1 KR930009814 B1 KR 930009814B1
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formula
bocmi
maleimide
butoxycarbonyl
tetrahydrophthalimide
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KR1019910010273A
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KR930000479A (en
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안광덕
이영훈
구덕일
정동욱
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한국과학기술연구원
박원희
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Priority to JP4024157A priority patent/JPH07116141B2/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
    • C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrrole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

This is a new N-tert-butoxycarbonylmaleimide (t-BOCMI) of formula (I) . The method comprises (A) reacting maleimide and furan and forming 3,6-epoxy- 1,2,3,6-tetrahydrophthalimide by Diels - Alder reaction; (B) making N-(t-butoxycarbonyl)3,6-epoxy- 1,2,3,6- tetrahydrophthalimide by reacting (A) and di-t- butyldicarbonate; and (C) heating and decomposing (B) in toluen and getting final product of (I). Total process yield is 87% and melting pt. of the product is 62 deg.C. The product is identified by IR, C13 and H1 NMR, MS, GC/MS, and component analysis. The above t-BOCMI is a very good resist material.

Description

N-터셔리-부톡시카르보닐말레이미드 단량체 제조방법N-tertiary-butoxycarbonylmaleimide monomer production method

본 발명은 산이나 열에 의한 분해가 용이하여 아미노기, 히드록실기등의 보호 및 탈보호 반응에 유리한 터셔리-부톡시카르보닐(tert-butoxycarbonyl : 이하 t-BOC으로 표시함)기를 말레이미드 단량체에 도입한 새로운 t-BOC보호 단량체인 N-tert-부톡시카르보닐말레이미드(N-t-butoxycarbonyl-maleimide : 이하 t-BOCMI로 표기함)의 제조방법에 관한 것이다.According to the present invention, a tert-butoxycarbonyl (hereinafter referred to as t-BOC) group which is easy to be decomposed by acid or heat and is advantageous for protection and deprotection reaction of amino group, hydroxyl group, etc., is incorporated into maleimide monomer. The present invention relates to a method for preparing N-tert-butoxycarbonyl maleimide (hereinafter referred to as t-BOCMI), which is a new t-BOC protecting monomer.

일반적으로 말레이미드와 그 유도체는 유기화합물로 유용하게 쓰이고 특히 라디칼 중합반응시 매우 반응성이 좋은 단량체로 쓰이며 그 중합체의 우수한 내열성 때문에 여러 분야에서 응용된다. 미국특허 제 2,444,536호에는 N-페닐말레이미드와 그 유도체가 살충제와 살균제로 유용함이 보고된 바 있고, 미국특허 2,526,517호에 따르면 N-메틸을 말레이미드는 약제, 염료, 가소제의 합성시 중간체로 이용된다고 발표한바 있다. 미국특허 3,035, 027호에 의하면, N-카바밀말레이미드의 여러가지 공중합체는 페인트, 옷, 종이와 같은 물질에 대한 보호막으로서 유용하다고 보고된 바 있다. 또한, 미국특허 4,266,005호에 따르면, N-치환된 말레이미드 고분자는 감광성 고분자 탄성체로 특별히 이용될 수 있다고 보고된 바 있다.In general, maleimide and its derivatives are useful as organic compounds, especially as monomers that are very reactive during radical polymerization, and are widely used in various fields because of their excellent heat resistance. US Patent No. 2,444,536 reported that N-phenylmaleimide and its derivatives are useful as insecticides and fungicides. According to US Patent No. 2,526,517, N-methyl is used as an intermediate in the synthesis of drugs, dyes and plasticizers. It has been announced. According to US Pat. No. 3,035,027, various copolymers of N-carbamylmaleimide have been reported to be useful as protective films for materials such as paints, clothes and paper. In addition, according to US Pat. No. 4,266,005, N-substituted maleimide polymers have been reported to be particularly used as photosensitive polymer elastomers.

말레이미드 구조는 그 독특한 내열성과 이미드기 프로톤의 극성기때문에 탈보호 전후에 있어서 용해도의 현저한 차이가 있어 레지스트 재료로도 크게 각광받고 있다. Turner, Ahn, Willson은 t-BOC보호된 N-(p-히드록시페닐)말레이미드 구조를 갖는 중합체가 원자외선 레지스트 재료로 이용가능하다고 보고하였다. 말레이미드의 질소에 관능 성기가 치환된 단량체 합성에 있어서 말레이미드에 직접반응으로 N-치환체를 도입하는 것은 불가능한 것으로 알려져 있다. Lester, Coleman등은 무수말레산과 지방족 아민으로부터 출발하여 N-치환된 말레이미드 유도체를-얻었고, R. C. P. Cubbon은 역시 같은 방법으로 t-부틸, N-이소부덜, N-에틸말레이미드를 합성하였다.Due to its unique heat resistance and polar group of the imide-based protons, the maleimide structure has a significant difference in solubility before and after deprotection, and thus has been widely spotlighted as a resist material. Turner, Ahn and Willson reported that polymers with t-BOC protected N- (p-hydroxyphenyl) maleimide structures are available as far ultraviolet resist materials. In the synthesis of monomers in which a functional group is substituted for nitrogen of maleimide, it is known that it is impossible to introduce N-substituents by direct reaction to maleimide. Lester, Coleman et al. Obtained N-substituted maleimide derivatives starting from maleic anhydride and aliphatic amines. R. C. P. Cubbon also synthesized t-butyl, N-isobuter and N-ethylmaleimide in the same manner.

이들 경우에 특히 N-치환체의 교기가 큰 경우에 수율이 매우 저조한 것으로 나타났다. 본 발명에 의한 t-BOCMI단량체 제조방법을 간단히 설명하면 우선 말레이마드의 이중결합을 퓨란(furan)으로 보호한 다음, t-B OC치환제롤 도입한 후 퓨란을 열분해 제거하여 t-BOCMI단량체를 제조한다In these cases, the yield was very low especially when the crosslinking of the N-substituent was large. Briefly describing the method for preparing t-BOCMI monomer according to the present invention, first, a double bond of Malaysia is protected with furan, followed by introducing a t-B OC substituent, followed by pyrolysis removal of the furan to prepare t-BOCMI monomer.

본 발명에 의하면, 치환체인 t-BOC기가 매우 큼에도 좋은 수율로 합성이 가능할뿐아니라 본 발명에 의하여 제조된 t-BOCMI단량체는 말레이미드에 t-BOC기가 도업되어 있어 감도와 내열성이 우수한 레지스트 재료의 제조에 적합하다.According to the present invention, not only the t-BOC group, which is a substituent, can be synthesized in a good yield, but also the t-BOCMI monomer prepared according to the present invention has a t-BOC group in maleimide, which is excellent in sensitivity and heat resistance. Suitable for the manufacture of

본 발명에 의한 t-BOCMI제조방법을 화학반응식으로 나타내면 다음과 같다.The t-BOCMI production method according to the present invention is represented by the following chemical reaction formula.

상기 화학반응식에서 알 수 있는 바와같이 말레이미드와 퓨란을 반응시키면 딜스-알더반응에 의하여 구조식(II)의 3, 6-에폭시-1, 2, 3, 6-테트라히드로프탈이미드가 정량적으로 생성되고, 구조식(II)화합물과 디-t-부틸디카보네이트(DTBDC)를 반응시키면 구조식(III)의 N-(t-부톡시카르보닐)-3, 6-에폭시-1,2,3,6-테트라히드로프탈이미드가 생성되고, 구조식(III)화합물을 토루엔중에서 가열하면 열분해하여 목적물인 구조식(I)의 t-B OCMI가 생성된다.As can be seen in the above chemical reaction, the reaction of maleimide with furan quantitatively generates 3, 6-epoxy-1, 2, 3, 6-tetrahydrophthalimide of formula (II) by Diels-Alder reaction. When the compound of formula (II) reacts with di-t-butyldicarbonate (DTBDC), N- (t-butoxycarbonyl) -3, 6-epoxy-1,2,3,6 of formula (III) Tetrahydrophthalimide is produced, and heating the compound of formula (III) in toluene to thermally decompose to produce tB OCMI of the formula (I).

생성된 t-BOCMI를 재결정한 바 수율은 87%였고, 그 녹는점(m, p)는 62℃였으며, 생성물을 적외선 분광분석, 탄소 및 양성자 핵자기 공명분석, 질량분석, 가스 크로마토그라피 결합 질량분광분석, 원소 분석한바, 그 구조가 t-BOCMI염이 확인되었다.The resulting t-BOCMI was recrystallized and the yield was 87%. The melting point (m, p) was 62 ° C. The product was subjected to infrared spectroscopy, carbon and proton nuclear magnetic resonance analysis, mass spectrometry, gas chromatography coupled mass. Spectroscopic analysis and elemental analysis showed that the structure was t-BOCMI salt.

본 발명으로 제조한 t-BOCMI단량체는 상업척으로 생산되는 일반 단량체와 용이하게 라디칼 공중합되고, 이로서 얻어진 중합체는 t-BOC보호기를 함유한 말레이미드 구조를 갖고있어서 산에 의하여 보호기 t-BOC기의 제거가 매우 쉽고, 보호기를 제거하여 얻어진 중합체는 말레이미드 구조로 200℃이상의 높은 유리천이온도를 갖는다. 그러므로 반도체의 초미세가공에서 플라즈마 드라이 엣칭(dry-etching)공정을 통한 패턴 이전(pattern transfer)공정등에서 레지스트의 미세화상이 200℃이상에서 내열성을 가져야하는 중요한 물성을 만족한다.The t-BOCMI monomer prepared according to the present invention is easily radically copolymerized with general monomers produced commercially, and the polymer thus obtained has a maleimide structure containing a t-BOC protecting group so that the t-BOC group is protected by acid. It is very easy to remove and the polymer obtained by removing the protecting group has a high glass transition temperature of 200 ° C. or more in the maleimide structure. Therefore, in the ultra-fine processing of semiconductors, in the pattern transfer process through the plasma dry etching process, the fine image of the resist satisfies the important physical property of having heat resistance at 200 ° C or higher.

또한, 서브 마크론 해상성 달성을 위하여 조사 파장이 단파장인 원자외선영역(deep UV, 200~300nm)또는 보다 유리하게 고출력의 불화 크립톤 엑사이머 레이저(KrF excimer laser)248nm 파장에서 레지스트의 광흡수가 높지않고 적절하여야 하는데 본 발명방법으로 제조한 t-BOCMI단량체를 함유하는 중합체는 원자외선 영역의 광흡수도가 매우 낮아서 원자외선 및 감방사선 레지스트 응용에 매우 적절한 고분자로 기대된다.In addition, in order to achieve submacro resolution, the light absorption of the resist in the deep UV region (200-300 nm) having a short wavelength or more advantageously in the high power KrF excimer laser 248 nm wavelength is achieved. The polymer containing the t-BOCMI monomer prepared by the method of the present invention is not high but is expected to be a very suitable polymer for the application of ultraviolet and radiation resist because of its very low light absorption in the far ultraviolet region.

이하, 본 발명을 몇가지 실시예를 들어 자세히 설명한다. 그러나, 이들 실시예가 본 발명을 한정하는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to several examples. However, these examples do not limit the present invention.

[실시예 1]Example 1

구조식(II) 화합물의 제조Preparation of Structural Formula (II) Compound

딜스-알더반응에 따라 반응용기에 말레이미드 25.0g(0.26mol)과 퓨란 28.0g(0.41mol), 톨루엔 100ml를 넣고 24시간 환류시켰다. 반응물을 실온으로 식히고 여과 및 건조하여 구조식(II) 화합물 42.0g(수율 99%)을 얻었다.According to the Diels-Alder reaction, 25.0 g (0.26 mol) of maleimide, 28.0 g (0.41 mol) of furan, and 100 ml of toluene were added and refluxed for 24 hours. The reaction was cooled to room temperature, filtered and dried to give 42.0 g (99% yield) of the compound of formula II.

[실시예 2]Example 2

구조식(III)화합물의 제조Preparation of Structural Formula (III) Compound

구조식(II)화합물 42.0g(0.26moℓ)을 취하여 디메틸 술폭사이드(DMSO)300ml에 녹이고 분말상의 포타시움 t-부톡사이드 35.0g(0.31mol)을 가하여 실온에서 30분동안 저어준후 디-t-부틸디카보네이트 62.0g(0.28mol)을 가하여 2시간 반응시켰다.42.0 g (0.26 mol) of the compound of formula (II) was dissolved in 300 ml of dimethyl sulfoxide (DMSO), and 35.0 g (0.31 mol) of powdered potassium fortium t-butoxide was added and stirred at room temperature for 30 minutes, followed by di-t-butyldi 62.0 g (0.28 mol) of carbonate was added and reacted for 2 hours.

반응물을 냉각시킨 증류수에 부어 침전시키고, 여과후 건조하여 구조식(III)의 흰색 분말 55.0g(수율81%)얻었다.The reaction was poured into cooled distilled water, precipitated, filtered and dried to give 55.0 g (81% yield) of a white powder of formula (III).

[실시예 3]Example 3

구조식(I)의 t-BOCMI 단량체 제조Preparation of t-BOCMI Monomer of Structural Formula (I)

구조식(III)화합물 10.0g을 취하여 톨루엔 100ml에 녹이고, 110℃내지 125℃의 오일중탕에서 1.5시간 환류시켜 열분해하였다. 톨루엔을 감압 증발시키고 얻어진 고체를 톨루엔과 헥산의(1:10의 체적비율)용매로 재결정하여 고순도의 t-BOCMI를 6.7g얻었다. (수율 90%)얻어진 t-BOCMI는 녹는점이 62℃로 관찰되었고 양성자 분광 분석에서 이중결합의 2개 프로톤(6.70ppm)과 t-BOC기의 9개 프로톤(1.60ppm)을 각각 단일 피크로 확인하였다. 적외선 분광 분석에서 t-부틸에 해당하는 2980cm-l및 이미드와 에스테르에 해당하는 1800, 1760, 1720cm-1의 흡수띠가 확인되었다. 탄소-13 양성자 분광 분석에서 t-부틸의 탄소가 85.24ppm, 올레핀의 탄소가 135.83ppm, 에스테르의 탄소가 145.88ppm, 말레이미드의 케톤 탄소가 166.22ppm에서 확인되었다.10.0 g of the compound of formula (III) was taken, dissolved in 100 ml of toluene, and pyrolyzed by refluxing for 1.5 hours in an oil bath of 110 ° C to 125 ° C. Toluene was evaporated under reduced pressure, and the obtained solid was recrystallized from a solvent of toluene and hexane (volume ratio of 1:10) to obtain 6.7 g of high purity t-BOCMI. (90% yield) The obtained t-BOCMI was observed to have a melting point of 62 ° C and two protons (6.70 ppm) of double bonds and nine protons (1.60 ppm) of t-BOC groups were identified as single peaks in proton spectroscopy. It was. The 2980cm -l already and absorption band of 1800, 1760, 1720cm -1 and corresponding to the de ester was observed for the t- butyl in infrared spectroscopic analysis. In the carbon-13 proton spectroscopic analysis, 85.24 ppm of t-butyl carbon, 135.83 ppm of olefin carbon, 145.88 ppm of carbon of ester, and 166.22 ppm of ketone carbon of maleimide were identified.

가스 크로마토 그라피 결합 질량 분광 분석으로부터 t-BOCMI분자에서 메틸기가 이탈된 이온 피크가 m/e=182에서, t-BOC기가 분해된 말레이미드의 이온 피크가 m/e=98에서, 이소프로펜에서 기인된 이소부탄의 이온피크가 m/e=57에서 나타남을 확인하였고 원소 분석으로부터 탄소가 54.70%, 수소가 5.60%, 질소가 7.18% 존재하는것으로 나타났고, 계산결과 C9H11NO4의 분자식을 가짐이 확인되었다.From the gas chromatographic binding mass spectrometry, the ion peak of the methyl group deviated from the t-BOCMI molecule is m / e = 182, the ion peak of the maleimide decomposed t-BOC group is m / e = 98, appeared was confirmed to appear in the ion peak at m / e = 57 of the resulting iso-butane from elemental analysis that the carbon is present 54.70%, hydrogen 5.60%, nitrogen 7.18%, the calculation result of C 9 H 11 NO 4 It was found to have a molecular formula.

Claims (3)

아래 구조식(I)의 N-터셔리-부톡시카르보닐 말레이미드(t-BOCMI)N-tertiary-butoxycarbonyl maleimide of formula (I) below (t-BOCMI) 말레이미드의 퓨란(furan)을 반응시켜 구조식(II)의 3, 6-에폭시-1, 2, 3, 6-테트라히드로프탈이미드를 제조하고, 구조식(II)화합물과 디-t-부틸디카보네이트를 반응시켜 구조식(III)의 N-(t-부톡시카르보닐)-3, 6-에폭시-1, 2, 3, 6-테트라히드로프탈이미드를 제조하고, 구조식(III)화합물을 톨루엔 중에서 가열분해하는 구조식(Ⅰ)의 N-터셔리-부톡시카르보닐말레이미드(t-BOCMI) 제조방법.The furan of maleimide is reacted to prepare 3, 6-epoxy-1, 2, 3, 6-tetrahydrophthalimide of formula (II), and a compound of formula (II) and di-t-butyldi The carbonate was reacted to prepare N- (t-butoxycarbonyl) -3, 6-epoxy-1, 2, 3, 6-tetrahydrophthalimide of formula (III), and toluene compound of formula (III) Method for producing N-tertiary-butoxycarbonylmaleimide (t-BOCMI) of Structural Formula (I) to be thermally decomposed in 제 2 항에 있어서, 가열온도가 110~125℃인 것이 특징인 N-터셔리-부톡시카르보닐말레이미드 제조방법.The method for producing N-tertiary-butoxycarbonylmaleimide according to claim 2, wherein the heating temperature is 110 to 125 ° C.
KR1019910010273A 1991-06-21 1991-06-21 Tert-butoxycarbonyl KR930009814B1 (en)

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