KR20000014213A - Photosensitive polymer having ring-shaped backbone and resist composition including photosensitive polymer - Google Patents
Photosensitive polymer having ring-shaped backbone and resist composition including photosensitive polymer Download PDFInfo
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- KR20000014213A KR20000014213A KR1019980033497A KR19980033497A KR20000014213A KR 20000014213 A KR20000014213 A KR 20000014213A KR 1019980033497 A KR1019980033497 A KR 1019980033497A KR 19980033497 A KR19980033497 A KR 19980033497A KR 20000014213 A KR20000014213 A KR 20000014213A
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- 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
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- 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
- C08F232/00—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F232/08—Copolymers of cyclic compounds containing no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having condensed rings
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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
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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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
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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
- G03F7/039—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
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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
- G03F7/039—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
- G03F7/0395—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 a backbone with alicyclic moieties
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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
- G03F7/039—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
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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
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
- G03F7/0758—Macromolecular compounds containing Si-O, Si-C or Si-N bonds with silicon- containing groups in the side chains
Abstract
Description
본 발명은 화학증폭형 레지스트 조성물에 관한 것으로, 특히 백본(backbone)이 환상(環狀) 구조를 가지는 감광성 폴리머 및 이를 포함하는 ArF 엑시머 레이저용 레지스트 조성물에 관한 것이다.The present invention relates to a chemically amplified resist composition, and more particularly, to a photosensitive polymer having a backbone having an annular structure and a resist composition for an ArF excimer laser including the same.
반도체 제조 공정이 복잡해지고 반도체 소자의 집적도가 증가함에 따라 미세한 패턴 형성이 요구된다.As the semiconductor manufacturing process becomes complicated and the degree of integration of semiconductor devices increases, fine pattern formation is required.
더욱이, 반도체 소자의 용량이 1기가(Giga) 비트 급 이상인 소자에 있어서, 디자인 룰이 0.2μm 이하인 패턴 사이즈가 요구되고, 그에 따라 기존의 KrF 엑시머 레이저(248nm)를 이용한 레지스트 재료를 사용하는 데 한계가 있다. 따라서, 새로운 에너지 노광원인 ArF 엑시머 레이저(193nm)를 이용한 리소그래피 기술이 등장하였다.Furthermore, in devices with a semiconductor device having a capacity of 1 gigabit or more, a pattern size of 0.2 μm or less is required for the design rule, thus limiting the use of a resist material using a conventional KrF excimer laser (248 nm). There is. Thus, a lithography technique using ArF excimer laser (193 nm), which is a new energy exposure source, has emerged.
이와 같은 ArF 엑시머 레이저를 이용한 리소그래피에 사용되는 레지스트 재료에서 가장 중요한 것은 투과도(transmittance)와 건식 식각에 대한 내성이다.In resist materials used in such liF excimer laser lithography, the most important is the transmittance and resistance to dry etching.
지금까지 알려진 일반적인 ArF 레지스트로서 아크릴계 또는 메타크릴계 폴리머들이 주로 사용되어 왔다. 이러한 폴리머들의 심각한 문제는 건식 식각에 대한 내성이 매우 약하여 실제 소자 개발에 적용할 수 없다는 것이다.Acrylic or methacrylic polymers have been mainly used as a general ArF resist known to date. A serious problem with these polymers is that they are very resistant to dry etching and cannot be applied to the actual device development.
따라서, 본 발명의 목적은 ArF용 레지스트가 가지는 단점을 극복하기 위한 것으로서, 건식 식각에 대한 내성을 충분히 확보할 수 있는 감광성 폴리머를 제공하는 것이다.Accordingly, an object of the present invention is to overcome the disadvantages of the ArF resist, and to provide a photosensitive polymer capable of sufficiently securing resistance to dry etching.
본 발명의 다른 목적은 ArF 엑시머 레이저를 이용하는 리소그래피에 사용하기 적합하도록 상기한 감광성 폴리머를 포함하는 레지스트 조성물을 제공하는 것이다.It is another object of the present invention to provide a resist composition comprising the photosensitive polymer described above for use in lithography using an ArF excimer laser.
상기 목적을 달성하기 위하여, 본 발명은 화학 증폭형 레지스트에 사용되는 다음 식을 가지는 감광성 폴리머를 제공한다.In order to achieve the above object, the present invention provides a photosensitive polymer having the following formula used in a chemically amplified resist.
식중, R1및 R3는 수소 또는 메틸기이고, R2는 C1∼ C20의 지방족 탄화수소이고, R4는 터트-부틸, 테트라히드로피라닐, 또는 1-알콕시에틸기이고, m/(m+n)은 0.1 ∼ 0.9이다.Wherein R 1 and R 3 are hydrogen or a methyl group, R 2 is a C 1 to C 20 aliphatic hydrocarbon, R 4 is a tert-butyl, tetrahydropyranyl or 1-alkoxyethyl group, m / (m + n) is 0.1-0.9.
상기 폴리머는 5,000 ∼ 100,000의 중량 평균 분자량을 갖는다.The polymer has a weight average molecular weight of 5,000 to 100,000.
R2는 C7∼ C20의 지환식(脂環式) 지방족 탄화수소, 바람직하게는 1-아다만탄 카르보닐기이다.R 2 is a C 7 to C 20 alicyclic aliphatic hydrocarbon, preferably 1-adamantane carbonyl group.
상기 다른 목적을 달성하기 위하여, 본 발명은In order to achieve the above another object, the present invention
(a) 화학 증폭형 레지스트에 사용되는 다음 식을 가지는 감광성 폴리머와,(a) a photosensitive polymer having the formula used in a chemically amplified resist,
식중, R1및 R3는 수소 또는 메틸기이고, R2는 C1∼ C20의 지방족 탄화수소이고, R4는 터트-부틸, 테트라히드로피라닐, 또는 1-알콕시에틸기이고, m/(m+n)은 0.1 ∼ 0.9임.Wherein R 1 and R 3 are hydrogen or a methyl group, R 2 is a C 1 to C 20 aliphatic hydrocarbon, R 4 is a tert-butyl, tetrahydropyranyl or 1-alkoxyethyl group, m / (m + n) is 0.1 to 0.9.
(b) PAG(photoacid generator)로 구성되는 레지스트 조성물을 제공한다.(b) provides a resist composition composed of a photoacid generator (PAG).
상기 레지스트 조성물은 상기 폴리머의 중량을 기준으로 1 ∼ 15 중량%의 PAG를 포함할 수 있다.The resist composition may include 1 to 15% by weight of PAG based on the weight of the polymer.
상기 PAG는 트리아릴술포늄염(triarylsulfonium salts), 디아릴이오도늄염(diaryliodonium salts) 및 유기 술포네이트로 이루어지는 군에서 선택되는 어느 하나 또는 그 혼합물이다. 바람직하게는, 상기 PAG는 트리페닐술포늄 트리플레이트, 디페닐이오도늄 트리플레이트 및 N-히드록시숙신이미드 트리플레이트로 이루어지는 군에서 선택되는 어느 하나 또는 그 혼합물이다.The PAG is any one or a mixture thereof selected from the group consisting of triarylsulfonium salts, diaryliodonium salts, and organic sulfonates. Preferably, the PAG is any one or mixture thereof selected from the group consisting of triphenylsulfonium triflate, diphenyliodonium triflate and N-hydroxysuccinimide triflate.
본 발명에 따른 레지스트 조성물은 유기 염기를 더 포함할 수 있다.The resist composition according to the present invention may further comprise an organic base.
상기 유기 염기는 상기 폴리머의 중량을 기준으로 0.01 ∼ 2.0 중량%의 양으로 포함된다.The organic base is included in an amount of 0.01 to 2.0% by weight based on the weight of the polymer.
상기 유기 염기는 트리에틸 아민 및 트리이소부틸 아민으로 이루어지는 군에서 선택되는 어느 하나 또는 그 혼합물이다. 바람직하게는, 상기 유기 염기는 디에탄올 아민 및 트리에탄올 아민으로 이루어지는 군에서 선택되는 어느 하나 또는 그 혼합물이다.The organic base is any one selected from the group consisting of triethyl amine and triisobutyl amine or mixtures thereof. Preferably, the organic base is any one or a mixture thereof selected from the group consisting of diethanol amine and triethanol amine.
본 발명에 의하면, 폴리머의 백본에 건식 식각에 대한 내성을 증가시킬 수 있는 지환식(脂環式) 화합물을 많이 함유하고 있으며, 이와 같은 폴리머로부터 얻어진 레지스트 조성물은 막질에 대한 접착 특성이 우수하다. 따라서, 본 발명에 따른 레지스트 조성물은 SLR(Single Layer Resist)용 재료로서 적합하다.According to the present invention, the polymer backbone contains a large amount of alicyclic compounds capable of increasing resistance to dry etching, and the resist composition obtained from such a polymer has excellent adhesion property to the film quality. Therefore, the resist composition according to the present invention is suitable as a material for SLR (Single Layer Resist).
다음에, 본 발명의 바람직한 실시예에 대하여 첨부 도면을 참조하여 상세히 설명한다.Next, a preferred embodiment of the present invention will be described in detail with reference to the accompanying drawings.
실시예 1Example 1
모노머의 합성Synthesis of Monomers
둥근 플라스크에 D-(+)-리보닉-γ-락톤(I)(0.11몰)을 트리에틸 아민(0.11몰)과 함께 무수 THF에 녹인 후, 여기에 메타크릴로일 클로라이드(0.1몰)를 천천히 떨어뜨렸다.In a round flask, D-(+)-ribonic-γ-lactone (I) (0.11 mol) was dissolved in anhydrous THF with triethyl amine (0.11 mol), and then methacryloyl chloride (0.1 mol) was added thereto. Dropped slowly.
반응물의 온도를 45℃로 하여 상기 혼합물을 약 12시간동안 반응시킨 후, 얻어진 반응물을 과량의 물에 부어 넣고, HCl을 이용하여 중화시켰다.After reacting the mixture for about 12 hours at a temperature of 45 ° C., the resulting reaction was poured into excess water and neutralized with HCl.
메틸렌 클로라이드를 이용하여 추출한 후, 생성물을 분리하였다(수율 70%).After extraction with methylene chloride, the product was isolated (yield 70%).
실시예 2Example 2
호모폴리머의 합성Synthesis of Homopolymer
실시예 1에서 합성한 모노머(40밀리몰)를 아조비스(이소부티로니트릴)(1.6밀리몰)와 함께 무수 THF에 녹인 후, 반응물을 환류 조건하에서 약 24시간동안 중합시켰다.The monomer (40 mmol) synthesized in Example 1 was dissolved in anhydrous THF with azobis (isobutyronitrile) (1.6 mmol) and then the reaction was polymerized for about 24 hours under reflux conditions.
중합이 완료된 후, 반응물을 과량의 n-헥산에서 침전시켰다. 다시 침전물을 THF에 녹이고, n-헥산에서 재침전시켰다.After the polymerization was complete, the reaction was precipitated in excess n-hexane. The precipitate was again dissolved in THF and reprecipitated in n-hexane.
침전물을 50℃로 유지되는 진공 오븐 내에서 24시간동안 건조시켰다(수율 75%).The precipitate was dried for 24 hours in a vacuum oven maintained at 50 ° C. (yield 75%).
이 때, 얻어진 생성물의 중량 평균 분자량은 15,600이었고, 다분산도(polydispersity)는 2.1이었다.At this time, the weight average molecular weight of the obtained product was 15,600 and polydispersity was 2.1.
실시예 3Example 3
호모폴리머의 개질(改質)Modification of Homopolymers
실시예 2에서 합성한 호모폴리머(50밀리몰)와 트리에틸아민(TEA)(50밀리몰)을 무수 THF에 녹인 후, 여기에 1-아다만탄 카르보닐 클로라이드(50밀리몰)를 천천히 떨어뜨렸다. 그 후, 반응물의 온도를 50℃로 하여 1시간동안 반응시켰다.The homopolymer (50 mmol) and triethylamine (TEA) (50 mmol) synthesized in Example 2 were dissolved in anhydrous THF, and 1-adamantane carbonyl chloride (50 mmol) was slowly dropped therein. Thereafter, the reaction mass was allowed to react at 50 ° C for 1 hour.
반응이 완료된 후, 반응물을 과량의 물에 천천히 떨어뜨리면서 침전시키고, 얻어진 침전물을 다시 THF에 녹인 후, n-헥산에서 재침전시켰다.After the reaction was completed, the reaction was precipitated while slowly dropping in excess water, and the obtained precipitate was dissolved in THF again and then re-precipitated in n-hexane.
침전물을 50℃로 유지되는 진공 오븐 내에서 24시간동안 건조시켰다(수율 80%).The precipitate was dried for 24 hours in a vacuum oven maintained at 50 ° C. (yield 80%).
실시예 4Example 4
코폴리머의 합성Synthesis of Copolymer
실시예 1에서 합성한 모노머(40밀리몰)와 터트-부틸 메타크릴레이트(tBMA)(40밀리몰)를 아조비스(이소부티로니트릴)(AIBN)(3.2밀리몰)과 함께 무수 THF에 녹인 후, 질소 가스를 사용하여 약 1시간동안 퍼지시켰다. 반응물을 환류 조건하에서 약 1시간동안 중합시켰다.The monomer (40 mmol) and tert-butyl methacrylate (tBMA) (40 mmol) synthesized in Example 1 were dissolved in anhydrous THF with azobis (isobutyronitrile) (AIBN) (3.2 mmol) and then nitrogen. The gas was used to purge for about 1 hour. The reaction was polymerized for about 1 hour under reflux conditions.
중합이 완료된 후, 반응물을 과량의 n-헥산에서 침전시켰다. 다시 침전물을 THF에 녹이고, n-헥산에서 재침전시켰다.After the polymerization was complete, the reaction was precipitated in excess n-hexane. The precipitate was again dissolved in THF and reprecipitated in n-hexane.
침전물을 50℃로 유지되는 진공 오븐 내에서 24시간동안 건조시켰다(수율 80%).The precipitate was dried for 24 hours in a vacuum oven maintained at 50 ° C. (yield 80%).
이 때, 얻어진 생성물의 중량 평균 분자량은 12,800이었고, 다분산도(polydispersity)는 2.2이었다.At this time, the weight average molecular weight of the obtained product was 12,800, and the polydispersity was 2.2.
실시예 5Example 5
코폴리머의 개질Modification of Copolymer
실시예 4에서 합성한 코폴리머(50밀리몰)와 트리에틸아민(TEA)(25밀리몰)을 THF에 녹인 후, 여기에 1-아다만탄 카르보닐 클로라이드(25밀리몰)를 천천히 떨어뜨리고, 반응물의 온도를 45℃로 하여 약 12시간동안 반응시켰다.After dissolving the copolymer (50 mmol) and triethylamine (TEA) (25 mmol) synthesized in Example 4 in THF, 1-adamantane carbonyl chloride (25 mmol) was slowly dropped thereinto, followed by The reaction was carried out at about 45 ° C. for about 12 hours.
반응이 완료된 후, 반응물을 과량의 물에서 천천히 침전시켰다. 그 후, 침전물을 THF에 녹이고 n-헥산에서 재침전시켰다.After the reaction was completed, the reaction was slowly precipitated in excess water. The precipitate was then dissolved in THF and reprecipitated in n-hexane.
침전물을 50℃로 유지되는 진공 오븐 내에서 24시간동안 건조시켰다(수율 80%).The precipitate was dried for 24 hours in a vacuum oven maintained at 50 ° C. (yield 80%).
실시예 6Example 6
레지스트 조성물Resist composition
실시예 4에서 합성한 코폴리머(1g)를 PAG(photoacid generator)인 트리페닐술포늄 트리플레이트(0.02g)와 함께 프로필렌 글리콜 모노메틸 에테르 아세테이트(PGMEA)(7g)에 완전히 용해시켰다. 그 후, 상기 용액을 0.2μm 멤브레인 필터(membrane filter)를 이용하여 걸러서 레지스트 조성물을 얻었다. 그 후, 이 레지스트 조성물을 헥사메틸디실라잔(HMDS)으로 처리한 실리콘 웨이퍼상에 약 0.5μm의 두께로 코팅하였다.The copolymer (1 g) synthesized in Example 4 was completely dissolved in propylene glycol monomethyl ether acetate (PGMEA) (7 g) together with triphenylsulfonium triflate (0.02 g), a photoacid generator (PAG). Thereafter, the solution was filtered using a 0.2 μm membrane filter to obtain a resist composition. This resist composition was then coated to a thickness of about 0.5 μm on a silicon wafer treated with hexamethyldisilazane (HMDS).
레지스트 조성물이 코팅된 상기 웨이퍼를 130℃의 온도에서 90초동안 프리베이킹(pre-baking)하고, 개구수(NA)가 0.45인 KrF 엑시머 레이저를 이용하여 노광한 후, 140℃의 온도에서 90초동안 PEB(post-exposure baking)를 실시하였다.The wafer coated with the resist composition was pre-baked for 90 seconds at a temperature of 130 ° C., exposed using a KrF excimer laser having a numerical aperture (NA) of 0.45, and then 90 seconds at a temperature of 140 ° C. PEB (post-exposure baking) was carried out.
그 후, 2.38 중량% 테트라메틸암모늄 히드록사이드(tetramethylammonium hydroxide: TMAH) 용액으로 현상한 결과, 23mJ/cm2의 노광 도즈량에서 0.3μm 라인 앤드 스페이스 패턴이 얻어지는 것을 확인하였다.Then, as a result of developing with a 2.38 weight% tetramethylammonium hydroxide (TMAH) solution, it was confirmed that a 0.3 micrometer line and space pattern is obtained at the exposure dose of 23mJ / cm <2> .
실시예 7Example 7
레지스트 조성물Resist composition
실시예 5에서 합성한 코폴리머(1g)를 PAG인 트리페닐술포늄 트리플레이트(0.02g)와 함께 PGMEA(7g) 용액에 완전히 용해시켰다. 그 후, 상기 용액을 0.2μm 멤브레인 필터를 이용하여 걸러서 레지스트 조성물을 얻었다. 그 후, 이 레지스트 조성물을 HMDS로 처리한 실리콘 웨이퍼상에 약 0.5μm의 두께로 코팅하였다.The copolymer (1 g) synthesized in Example 5 was completely dissolved in PGMEA (7 g) solution together with triphenylsulfonium triflate (0.02 g), PAG. The solution was then filtered using a 0.2 μm membrane filter to obtain a resist composition. This resist composition was then coated to a thickness of about 0.5 μm on a silicon wafer treated with HMDS.
레지스트 조성물이 코팅된 상기 웨이퍼를 140℃의 온도에서 90초동안 프리베이킹(pre-baking)하고, 개구수(NA)가 0.45인 KrF 엑시머 레이저를 이용하여 노광한 후, 140℃의 온도에서 90초동안 PEB를 실시하였다.The wafer coated with the resist composition was pre-baked for 90 seconds at a temperature of 140 ° C, exposed using a KrF excimer laser having a numerical aperture (NA) of 0.45, and then 90 seconds at a temperature of 140 ° C. PEB was performed.
그 후, 2.38 중량% TMAH 용액으로 약 60초 동안 현상하였다. 그 결과, 노광 도즈량을 26mJ/cm2으로 하였을 때 0.3μm 라인 앤드 스페이스 패턴이 얻어지는 것을 확인하였다.It was then developed for about 60 seconds with a 2.38 wt% TMAH solution. As a result, it was confirmed that a 0.3 μm line-and-space pattern was obtained when the exposure dose was 26 mJ / cm 2 .
실시예 8Example 8
리소그래피 퍼포먼스Lithography Performance
실시예 5에서 합성한 코폴리머(m/(m+n)=0.6, 중량 평균 분자량=14,700](1g)를 PAG인 트리페닐술포늄 트리플레이트(0.02g)와 함께 PGMEA(7g) 용액에 완전히 용해시켰다. 그 후, 여기에 유기 염기로서 트리이소부틸 아민(2mg)을 첨가하고 완전히 용해시켰다.The copolymer (m / (m + n) = 0.6, weight average molecular weight = 14,700] (1 g) synthesized in Example 5 was completely added to the PGMEA (7 g) solution together with triphenylsulfonium triflate (0.02 g), which is PAG. Thereafter, triisobutyl amine (2 mg) was added thereto as an organic base and completely dissolved.
상기 용액을 0.2μm 멤브레인 필터를 이용하여 걸러서 레지스트 조성물을 얻었다. 그 후, 이 레지스트 조성물을 HMDS로 처리한 실리콘 웨이퍼상에 약 0.5μm의 두께로 코팅하였다.The solution was filtered using a 0.2 μm membrane filter to obtain a resist composition. This resist composition was then coated to a thickness of about 0.5 μm on a silicon wafer treated with HMDS.
레지스트 조성물이 코팅된 상기 웨이퍼를 140℃의 온도에서 90초동안 프리베이킹(pre-baking)하고, 개구수(NA)가 0.45인 KrF 엑시머 레이저를 이용하여 노광한 후, 140℃의 온도에서 90초동안 PEB를 실시하였다.The wafer coated with the resist composition was pre-baked for 90 seconds at a temperature of 140 ° C, exposed using a KrF excimer laser having a numerical aperture (NA) of 0.45, and then 90 seconds at a temperature of 140 ° C. PEB was performed.
그 후, 2.38 중량% TMAH 용액으로 약 60초 동안 현상하였다. 그 결과, 노광 도즈량을 약 40mJ/cm2으로 하였을 때 0.3μm 라인 앤드 스페이스 패턴이 얻어지는 것을 확인하였다.It was then developed for about 60 seconds with a 2.38 wt% TMAH solution. As a result, it was confirmed that a 0.3 μm line-and-space pattern was obtained when the exposure dose was set to about 40 mJ / cm 2 .
본 발명에 의하면, 아크릴레이트계 또는 메타크릴레이트계의 폴리머 백본에 건식 식각 내성을 증가시키는 지환식 화합물을 많이 함유할 수 있는 구조를 가지는 폴리머를 제공한다. 이로부터 얻어지는 레지스트 조성물은 건식 식각에 대한 내성이 우수할 뿐 만 아니라 막질에 대한 접착 특성이 우수하다. 본 발명에 따른 레지스트 조성물은 SLR(Single Layer Resist)용 재료로서 적합하다.According to the present invention, a polymer having a structure capable of containing a large amount of alicyclic compounds for increasing dry etching resistance in an acrylate-based or methacrylate-based polymer backbone is provided. The resist composition obtained therefrom is not only excellent in resistance to dry etching but also excellent in adhesion properties to film quality. The resist composition according to the present invention is suitable as a material for SLR (Single Layer Resist).
이상, 본 발명을 바람직한 실시예를 들어 상세하게 설명하였으나, 본 발명은 상기 실시예에 한정되지 않고, 본 발명의 기술적 사상의 범위 내에서 당 분야에서 통상의 지식을 가진 자에 의하여 여러가지 변형이 가능하다.The present invention has been described in detail with reference to preferred embodiments, but the present invention is not limited to the above embodiments, and various modifications can be made by those skilled in the art within the scope of the technical idea of the present invention. Do.
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