KR20030064056A - ESCAP and t-BOC type of DUV resist compound - Google Patents

ESCAP and t-BOC type of DUV resist compound Download PDF

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KR20030064056A
KR20030064056A KR1020020004483A KR20020004483A KR20030064056A KR 20030064056 A KR20030064056 A KR 20030064056A KR 1020020004483 A KR1020020004483 A KR 1020020004483A KR 20020004483 A KR20020004483 A KR 20020004483A KR 20030064056 A KR20030064056 A KR 20030064056A
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resist
compound
escap
boc
duv
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안덕근
하현주
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주식회사 하이닉스반도체
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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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • 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
    • C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F212/02—Monomers containing only one unsaturated aliphatic radical
    • C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F212/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by heteroatoms or groups containing heteroatoms
    • C08F212/22—Oxygen
    • C08F212/24—Phenols or alcohols
    • 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
    • C08F220/10—Esters
    • C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
    • C08F220/343—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links
    • C08F220/346—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate in the form of urethane links and further oxygen
    • 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
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • 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
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/30—Imagewise removal using liquid means
    • G03F7/32—Liquid compositions therefor, e.g. developers
    • G03F7/322—Aqueous alkaline compositions

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)

Abstract

PURPOSE: An ESCAP-t-BOC-combined compound for deep ultraviolet (DUV) resist and a photolithography method using the compound are provided, to minimize the loss of resist, to enable an etching process to be performed easily and to improve the CD uniformity. CONSTITUTION: The compound comprises an ESCAP part and a t-BOC part and is represented by the formula, wherein n1 is an integer of 0-10; n2 is an integer of 0-2; and R' is an aromatic group or an aliphatic group. Preferably R' is an aromatic group of C6-C18 or an aliphatic group of C1-C20. Preferably the pattern of semiconductor is prepared by using the resist containing the compound of the formula, and can be developed by using only deionized water without using a basic developer.

Description

ＥＳＣＡＰ와 ｔ-ＢＯＣ 혼합형의 ＤＵＶ 레지스트용 화합물{ESCAP and t-BOC type of DUV resist compound}ESCAP and t-BOC type of DUV resist compound

본 발명은 DUV 레지스트용 화합물 및 상기 화합물을 이용하는 포토리소그래피(photolithography) 방법에 관한 것이다. 보다 상세하게, 본 발명은 아미노산을 이용하여 ESCAP와 t-BOC 혼합형의 DUV 레지스트용 화합물을 형성하고, 그렇게 형성된 화합물을 이용하여 반도체 패턴을 형성하는 포토리소그래피 방법에 관한 것이다.The present invention relates to a compound for a DUV resist and a photolithography method using the compound. More specifically, the present invention relates to a photolithography method in which a compound for DUV resist of ESCAP and t-BOC mixed type is formed using amino acids, and a semiconductor pattern is formed using the compound so formed.

반도체 제조 공정이 복잡해지고 집적도가 증가함에 따라서, 사진 공정에서는 보다 미세한 패턴의 구현이 요구되고, 그에 따라 새로운 포토레지스트 재료의 개발이 필수 과제가 되고 있다. 또한 식각 공정과의 연계 또한 대단히 중요한 문제로 대두되고 있다.As the semiconductor fabrication process becomes more complex and the degree of integration increases, the implementation of finer patterns is required in the photolithography process, and thus, the development of new photoresist materials becomes an essential task. In addition, the linkage with the etching process is also an important issue.

일반적으로, 248 nm의 파장을 이용하는 사진 공정에서는 DUV(Deep Ultra Violet)용 레지스트를 이용하고 있으며, 이러한 DUV용 레지스트는 크게 t-BOC, ESCAP, 그리고 아세탈 타입으로 나눌 수 있다. 이들 레지스트는 미국과 일본 등의 전문적인 레지스트 제조회사를 통해 공급 받아 사용되고 있으며, 화학증폭형 레지스트(chemically amplified resist: CAR)이다.In general, a deep ultra violet (DUV) resist is used in a photo process using a wavelength of 248 nm, and the DUV resist can be roughly divided into t-BOC, ESCAP, and acetal types. These resists are supplied and used by professional resist manufacturers in the United States and Japan, and are chemically amplified resists (CARs).

"화학 증폭" 메카니즘에 근거한 DUV 레지스트는 약 2.5 ㎛ 이하에서의 패턴 분해능과 감도가 높기 때문에 점차 보편화되어 가고 있다. 이들 시스템은, 화학적으로 분해하여 페놀 또는 카르복실산을 생성하는 기에 의하여 페놀 또는 카르복실산 유래의 기들이 부분적으로 보호 또는 블로킹(blocking)되는 폴리머에 전형적으로 그 기초를 두고 있다. 따라서, DUV용 레지스트에 의한 현상 시에 용해도 차이를 나타낸다.DUV resists based on the "chemical amplification" mechanism are becoming increasingly common due to their high pattern resolution and sensitivity at about 2.5 μm or less. These systems are typically based on polymers in which groups derived from phenol or carboxylic acid are partially protected or blocked by groups that chemically decompose to produce phenol or carboxylic acid. Therefore, the difference in solubility at the time of development by the resist for DUV is shown.

이들 레지스트에 혼합되어 있는 산발생물질은 노광에 의해 산을 발생시키고, 이렇게 발생된 산은 레지스트의 탈보호기 반응을 유발시켜 비친수성 물질을 친수성 물질로 전환시키며, 최종적으로 염기성 현상액(TMAH)에 의해 패턴이 형성된다.The acid generators mixed in these resists generate an acid upon exposure, and the acid generated thus causes a deprotection reaction of the resist to convert the non-hydrophilic material into a hydrophilic material, and finally, the pattern is developed by a basic developer (TMAH). Is formed.

도 1을 참고하여 보면, 기존의 ESCAP 타입의 레지스트는 탈리부분인 에스테르 그룹이 발생된 산에 의해 친수성인 카르복실산으로 변형된 후 염기성 현상액에 의해 최종적으로 패턴을 형성하는 메카니즘에 따른다.Referring to Figure 1, the existing ESCAP type of resist is followed by a mechanism of finally forming a pattern by the basic developer after the desaturated ester group is transformed into hydrophilic carboxylic acid by the generated acid.

그러나 이러한 방법은 염기성 현상액을 사용함으로써 종종 레지스트 손실을 가져오고 또한 CD 균일성(critical dimension uniformity)에 나쁜 영향을 미치는 등의 문제점을 가지고 있다.However, this method has problems such as the use of a basic developer, which often results in resist loss and also adversely affects CD dimension uniformity.

따라서, 최근에는, 기본적으로 사용되고 있는 현상액(예, TMAH)의 농도를 감소시키려는 노력이 진행되고 있다.Therefore, in recent years, efforts have been made to reduce the concentration of the developer (eg TMAH) that is basically used.

이와 같은 문제점을 해결하기 위해서, 본 발명은 포토리소그래피 방법에서 가장 중요한 재료인 레지스트의 개발을 통해 보다 우수한 패턴 형성을 하기 위해, 아민기와 카르복실산기에 각각 보호기가 도입된 아미노산을 이용하여 ESCAP와 t-BOC 혼합형 레지스트를 제공하는 것을 목적으로 한다.In order to solve the above problems, the present invention uses ESCAP and t by using amino acids each of which has a protecting group introduced into an amine group and a carboxylic acid group in order to form a better pattern through the development of a resist, which is the most important material in the photolithography method. It is an object to provide a -BOC mixed resist.

본 발명의 다른 목적은 포토리소그래피 방법에서, CD 균일성을 높이고 현상 후 발생하는 레지스트의 손실을 줄이기 위해서 상기 ESCAP와 t-BOC 혼합형 레지스트를 사용하여 반도체의 패턴을 구현하도록 하는 것이다.Another object of the present invention is to implement a pattern of a semiconductor using the ESCAP and t-BOC mixed resist in order to increase the CD uniformity and to reduce the loss of resist generated after development in the photolithography method.

본 발명의 또 다른 목적은 포토리소그래피 방법에서, 상기 ESCAP와 t-BOC 혼합형 레지스트를 사용하여 종래의 염기성 현상액을 적게 사용하거나, 또는 전혀 사용하지 않고 탈이온수만을 이용할 수 있도록 하는 것이다.It is still another object of the present invention to use the ESCAP and t-BOC mixed resist in the photolithography method so that only deionized water can be used with little or no conventional basic developer.

도 1은 종래의 ESCAP형 레지스트의 패턴 형성 메카니즘을 보여주는 도면.1 shows a pattern formation mechanism of a conventional ESCAP type resist.

도 2는 본 발명에 따른 ESCAP와 t-BOC 혼합형의 DUV 레지스트용 화합물의 패턴 형성 메카니즘을 보여주는 도면.2 is a view showing a pattern formation mechanism of the compound for DUV resist of ESCAP and t-BOC mixed type according to the present invention.

상기 목적을 해결하기 위해서, 본 발명은 하기 화학식으로 이루어진 ESCAP와 t-BOC 혼합형의 DUV 레지스트용 화합물을 제공한다:In order to solve the above object, the present invention provides a compound for DUV resist of ESCAP and t-BOC mixed type consisting of the following formula:

상기 화학식에서, n1은 0 내지 10 사이의 정수이고, n2는 0 내지 2 사이의 정수이고, R'은 방향족 화합물 또는 지방족 화합물이다.In the above formula, n1 is an integer between 0 and 10, n2 is an integer between 0 and 2, and R 'is an aromatic compound or an aliphatic compound.

바람직하게, 상기 R'은 탄소수가 6 내지 18개의 방향족 화합물이거나, 또는 탄소수가 1 내지 20개의 지방족 화합물일 수 있다.Preferably, R 'may be an aromatic compound having 6 to 18 carbon atoms or an aliphatic compound having 1 to 20 carbon atoms.

또한, 본 발명은 상기 ESCAP와 t-BOC 혼합형의 DUV 레지스트용 화합물을 포함하는 레지스트를 사용하여 반도체의 패턴을 형성하는 포토리소그래피 방법을 제공한다.The present invention also provides a photolithography method for forming a pattern of a semiconductor using a resist containing the ESCAP and t-BOC mixed compound for DUV resist.

상기 포토리소그래피 방법은 본 발명에 따른 ESCAP와 t-BOC 혼합형의 DUV 레지스트용 화합물을 포함한 레지스트를 사용하기 때문에, 종래의 문제를 일으키던 현상액을 적게 사용할 수 있거나, 심지어는 현상액을 전혀 사용하지 않고 탈이온수(DI water)만으로 현상할 수도 있다.Since the photolithography method uses a resist containing a compound for an ESCAP and t-BOC mixed DUV resist according to the present invention, it is possible to use less developer, or even without using any developer, which causes a conventional problem. It can also be developed with (DI water) alone.

본 발명은 도 2를 참고하여 보다 상세히 설명할 수 있다. 그러나, 본 발명은 이에 한정되는 것은 아니다.The present invention can be described in more detail with reference to FIG. 2. However, the present invention is not limited to this.

도 2에 도시된 바와 같이, 염기성을 띠는 아민기와 산성을 띠는 카르복실산기를 모두 가지고 있는 아미노산을 레지스트로 도입하기 위해서, 일단 알코올을 이용하여 아미노산의 카르복실산기에 에스테르형 보호기를 형성한다.As shown in Fig. 2, in order to introduce an amino acid having both a basic amine group and an acidic carboxylic acid group into the resist, an ester type protecting group is once formed using an alcohol using an alcohol. .

이어서 t-BOC를 이용하여 아미노산의 아민기에 t-BOC형 보호기를 형성하여 본 발명에 따른 ESCAP와 t-BOC 혼합형 화합물을 얻었다. 그 후 기존의 레지스트에서 사용하고 있는 산발생물질을 혼합하여 레지스트를 제조한다.Subsequently, a t-BOC type protecting group was formed by using t-BOC to the amine group of the amino acid to obtain an ESCAP and t-BOC mixed compound according to the present invention. Thereafter, a resist is prepared by mixing an acid generator used in the existing resist.

이렇게 제조된 레지스트는 일반 공정인 노광 공정을 통해 발생된 산에 의해아미노산으로 환원되고, 환원된 아미노산은 분자간 또는 분자내 반응을 통해 염기성 현상액이 아닌 DI수에 의해서도 제거가 용이한 염의 형태로 변환된다. 이렇게 함으로써 패턴을 형성하게 된다.The resist thus prepared is reduced to an amino acid by an acid generated through an exposure process, which is a general process, and the reduced amino acid is converted into a salt form that is easily removed by DI water rather than a basic developer through an intermolecular or intramolecular reaction. . In this way, a pattern is formed.

따라서, 본 발명은 새로운 타입의 레지스트를 제공함으로써 염기성 현상액 대신 탈이온수만을 사용하는 현상을 가능하게 하고, 레지스트 손실을 최소화하여, 식각 공정에 용이하며, CD 균일성도 향상된 패턴 구현이 가능하게 된다.Accordingly, the present invention enables the development of using only deionized water instead of the basic developer by providing a new type of resist, minimizing the resist loss, enabling the etching process and improving the CD uniformity.

또한 점점 패턴의 미세화가 진행되고 있는 시점에서 보다 미세한 패턴의 구현은 레지스트의 두께를 얇은 형태로 가져가야 함에 따라 식각 공정의 부담이 커지고 있는 시점을 고려하면 본 새로운 변형 레지스트는 보다 가치가 있는 발명이라 생각되며, 염기성 현상액 대신 탈이온수에 의한 현상이 가능해짐에 따라 공정비용 절감 효과도 창출될 것으로 예상된다.In addition, when the pattern is being refined, the new modified resist is more valuable in view of the time when the burden of the etching process is increased as the thickness of the resist must be thin in the form of the resist. As it is possible to develop by deionized water instead of basic developer, it is expected to reduce the process cost.

Claims (5)

하기 화학식으로 이루어진 ESCAP와 t-BOC 혼합형의 DUV 레지스트용 화합물:Compound for DUV resist of ESCAP and t-BOC mixed type consisting of the following formula: (상기 화학식에서, n1은 0 내지 10 사이의 정수이고, n2는 0 내지 2 사이의 정수이고, R'은 방향족 화합물 또는 지방족 화합물임.)(In the above formula, n1 is an integer between 0 and 10, n2 is an integer between 0 and 2, and R 'is an aromatic compound or an aliphatic compound.) 제 1 항에 있어서,The method of claim 1, 상기 R'은 탄소수가 6 내지 18개의 방향족 화합물인 ESCAP와 t-BOC 혼합형의 DUV 레지스트용 화합물.R 'is a compound for DUV resist of ESCAP and t-BOC mixed type having 6 to 18 carbon atoms. 제 1 항에 있어서,The method of claim 1, 상기 R'은 탄소수가 1 내지 20개의 지방족 화합물인 ESCAP와 t-BOC 혼합형의 DUV 레지스트용 화합물.The R 'is a compound for DUV resist of ESCAP and t-BOC mixed type having 1 to 20 carbon atoms aliphatic compound. 제 1 항 내지 제 3 항 중 어느 한 항의 DUV 레지스트용 화합물을 포함하는 레지스트를 이용하여 반도체 패턴을 형성하는 포토리소그래피 방법.A photolithography method for forming a semiconductor pattern using a resist comprising the compound for a DUV resist according to any one of claims 1 to 3. 제 4 항에 있어서,The method of claim 4, wherein 염기성 현상액을 사용하지 않고 탈이온수(DI water)만으로 현상하는 단계를 포함하는 포토리소그래피 방법.A photolithography method comprising developing with DI water only without using a basic developer.
KR1020020004483A 2002-01-25 2002-01-25 ESCAP and t-BOC type of DUV resist compound KR20030064056A (en)

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