KR100218743B1 - Arf photoresist having a good adhesion - Google Patents

Arf photoresist having a good adhesion Download PDF

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KR100218743B1
KR100218743B1 KR1019960080257A KR19960080257A KR100218743B1 KR 100218743 B1 KR100218743 B1 KR 100218743B1 KR 1019960080257 A KR1019960080257 A KR 1019960080257A KR 19960080257 A KR19960080257 A KR 19960080257A KR 100218743 B1 KR100218743 B1 KR 100218743B1
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carboxylate
copolymer
cyclopentene
norbornene
bicyclo
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KR1019960080257A
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Korean (ko)
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KR19980060890A (en
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정재창
강수진
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김영환
현대전자산업주식회사
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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
    • 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
    • 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
    • G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents

Abstract

본 발명은 원 자외선 영역에서 사용될 수 있는 새로운 포토레지스트 물질로서 2-히드록시에틸아크릴레이트 유도체와 하나 또는 2 이상의 지방족 환형 올레핀의 공중합체에 관한 것이다. 본 발명의 공중합체는 접착성이 뛰어난 감광막을 제공할 수 있다.The present invention relates to copolymers of 2-hydroxyethylacrylate derivatives with one or more aliphatic cyclic olefins as new photoresist materials that can be used in the far ultraviolet region. The copolymer of this invention can provide the photosensitive film excellent in adhesiveness.

Description

접착성이 뛰어난 ArF 감광막 수지ArF photoresist resin with excellent adhesion

본 발명은 신규한 감광막 수지에 관한 것이며, 보다 상세하게는 고집적 반도체 소자의 미세회로 제작시, ArF (193) 광원을 사용한 광리소그래피 공정에서 포토레지스트의 수지로서 사용할 수 있는 신규한 공중합체, 그의 제조 방법 및 이를 함유하는 포토레지스트에 관한 것이다.BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel photoresist film resin, and more particularly, to ArF (193) in the manufacture of microcircuits of highly integrated semiconductor devices. The present invention relates to a novel copolymer which can be used as a resin of a photoresist in a photolithography process using a light source, a method for producing the same, and a photoresist containing the same.

반도체 제조의 미세 가공 공정에서 고감도를 달성하기 위해, 근래에는 화학 증폭성인 DUV(Deep Ultra Violet) 포토레지스트가 각광을 받고 있으며, 그 조성은 광산 발생제(photoacid generator)과 산에 민감하게 반응하는 구조의 매트릭스 고분자를 배합하여 제조한다.In order to achieve high sensitivity in the microfabrication process of semiconductor manufacturing, chemically amplifying deep ultra violet (DUV) photoresist has recently been in the spotlight, and its composition is sensitive to photoacid generators and acids. It is prepared by blending the matrix polymer.

이러한 포토레지스트의 작용 기전은 광산발생제가 광원으로부터 자외선 빛을 받게 되면 산을 발생시키고, 이렇게 발생된 산에 의해 매트릭스 고분자의 주쇄 또는 측쇄가 반응하여 분해되거나, 가교결합 또는 고분자의 극성이 크게 변하여, 현상액에 의해 용해되어 없어지게 된다. 반면, 빛을 받지 않은 부분은 본래의 구조를 그대로 갖기 때문에 현상액에 녹아 없어지지 않게 된다. 이렇게 하여 마스크의 상을 기판위에 양화상으로 남길 수 있게 된다. 이와 같은 리소그래피 공정에서 해상도는 광원의 파장에 의존하여, 광원의 파장이 작아질수록 미세패턴을 형성시킬 수 있다.The action mechanism of the photoresist is that when the photoacid generator receives ultraviolet light from the light source, it generates an acid, and the generated acid reacts with the main chain or side chain of the matrix polymer, or crosslinks or the polarity of the polymer changes greatly. It is dissolved by the developer and disappears. On the other hand, the part which does not receive light does not melt | dissolve in a developing solution because it has an original structure as it is. In this way, the mask image can be left as a positive image on the substrate. In such a lithography process, the resolution is dependent on the wavelength of the light source, so that the smaller the wavelength of the light source can form a fine pattern.

일반적으로 포토레지스트는 ArF 광에 대한 투명성, 에칭 내성성 2.38테트라메틸암모늄하이드록사이드(TMAH) 수용액에 현상가능성, 접착성 등의 성질을 만족하여야 하나, 이들 모든 성질을 만족하는 감광막 수지를 합성하기는 매우 어렵다. 특히, 패턴 크기가 0.15이하인 경우는 패턴의 무너짐 현상이 발생한다.In general, photoresists are transparent, etch resistant to ArF light 2.38 Although the properties of developability, adhesiveness, and the like must be satisfied in an aqueous solution of tetramethylammonium hydroxide (TMAH), it is very difficult to synthesize a photoresist resin that satisfies all these properties. Specifically, the pattern size is 0.15 In the following cases, collapse of the pattern occurs.

이에 본 발명자들은 이와같은 패턴의 무너짐 현상을 방지하기 위해 접착성이 매우 우수한 2-히드록시에틸아크릴레이트 유도체를 수지에 도입함으로써 감광막의 접착성을 매우 증가시킬 수 있다는 것을 확인하고 본 발명의 완성하게 되었다.Therefore, the present inventors have confirmed that the adhesion of the photosensitive film can be greatly increased by introducing a 2-hydroxyethyl acrylate derivative having excellent adhesiveness into the resin to prevent the collapse of such a pattern. It became.

그러므로, 본 발명의 목적은 접착성을 증가시킨 신규한 공중합체를 제공하는 것이다.Therefore, it is an object of the present invention to provide novel copolymers with increased adhesion.

본 발명의 다른 목적은 상기 공중합체를 제조하는 방법을 제공하는 것이다.Another object of the present invention is to provide a method for preparing the copolymer.

또한 본 발명의 또 다른 목적은 상기 신규한 공중합체를 함유하는 포토레지스트를 제공하는 것이다.Still another object of the present invention is to provide a photoresist containing the novel copolymer.

본 발명의 신규한 포토레지스트용 중합체는 하기 화학식 1 의 2-히드록시에틸아크릴레이트 유도체와 하나 또는 2 이상의 지방족 환형 올레핀과의 공중합체이다.The novel photoresist polymer of the present invention is a copolymer of a 2-hydroxyethyl acrylate derivative of formula (1) with one or more aliphatic cyclic olefins.

상기식에서, R은 수소 또는 메틸이다.Wherein R is hydrogen or methyl.

본 발명의 공중합체에서 지방족 환형 올레핀 단위체는 바람직하게는 하기 화학식 2 의 지방족 환형 올레핀, 즉 비닐렌 카르보네이트, 2-시클로펜텐-1-아세트산, 2-시클로펜텐-1-(t-부틸 아세테이트), 비시클로[2,2,2]옥트-5-엔-2-t-부틸 카르복실레이트, 비시클로[2,2,2]옥트-5-엔-2-카르복실산, 비시클로[2,2,2]옥트-5-엔-2-(2-히드록시에틸)카르복실레이트, 2-(2-하이드록시에틸)카르복실레이트-5-노르보넨, 2-t-부톡시 카르복실레이트-5-노르보넨, 2-카르복실산-5-노르보넨, 시클로펜텐, 시클로헥센, 노르보닐렌, 및 노르보닐렌-2-메탄올로 구성된 그룹에서 선택된 것이다.Aliphatic cyclic olefin units in the copolymer of the present invention are preferably aliphatic cyclic olefins represented by the following formula (2): vinylene carbonate, 2-cyclopentene-1-acetic acid, 2-cyclopentene-1- (t-butyl acetate ), Bicyclo [2,2,2] oct-5-ene-2-t-butyl carboxylate, bicyclo [2,2,2] oct-5-ene-2-carboxylic acid, bicyclo [ 2,2,2] oct-5-ene-2- (2-hydroxyethyl) carboxylate, 2- (2-hydroxyethyl) carboxylate-5-norbornene, 2-t-butoxy carbox Selected from the group consisting of carboxylate-5-norbornene, 2-carboxylic acid-5-norbornene, cyclopentene, cyclohexene, norbornylene, and norbornylene-2-methanol.

본 발명의 바람직한 공중합체의 분자량은 3,000 내지 200,000이다.Preferred copolymers of the present invention have a molecular weight of 3,000 to 200,000.

본 발명의 신규한 공중합체를 제조하는 방법은 화학식 1 의 2-히드록시에틸아크릴 유도체와 하나 또는 2 이상의 지방족 환형 올레핀 화합물을 통상의 라디칼 중합개시제를 사용하여 통상의 라디칼 중합함으로써 제조할 수 있다.The process for preparing the novel copolymers of the present invention can be prepared by conventional radical polymerization of a 2-hydroxyethylacrylic derivative of formula 1 with one or more aliphatic cyclic olefin compounds using conventional radical polymerization initiators.

이들은 벌크 중합 및 용액중합 등을 통하여 중합시키며, 중합용매로는 시클로헥사논, 메틸케틸케톤, 벤젠, 톨루엔, 디옥산, 디메텔포름아미드 등의 단독용매 또는 이들의 혼합용매를 사용할 수 있다. 중합개시제로는 벤조일퍼옥시드, 2,2'-아조비스이소부티로니트릴(AIBN), 아세틸퍼옥시드, 라우릴퍼옥시드, t-부틸퍼아세테이트 등을 사용할 수 있다.These are polymerized through bulk polymerization and solution polymerization, and a single solvent such as cyclohexanone, methyl ketil ketone, benzene, toluene, dioxane, dimethelformamide, or a mixed solvent thereof may be used as the polymerization solvent. As the polymerization initiator, benzoyl peroxide, 2,2'-azobisisobutyronitrile (AIBN), acetyl peroxide, lauryl peroxide, t-butyl peracetate and the like can be used.

본 발명의 신규한 포토레지스트 공중합체는 통상의 포토레지스트 조성물 제조와 같은 방법을 사용하여 유기용매에 통상의 광산 발생제와 혼합하여 포토레지스트 용액을 제조함으로써 포지티브 미세화상 형성에 사용할 수 있다.The novel photoresist copolymer of the present invention can be used for positive microimage formation by preparing a photoresist solution by mixing with a conventional photoacid generator in an organic solvent using the same method as for preparing a conventional photoresist composition.

본 발명의 공중합체의 사용량은 유기용매, 광산 발생제, 및 리소스그래피 조건등에 따라 변할 수 있으나, 대체로 포토레지스트 제조시 사용하는 유기용매에 대해 약 10 내지 30 중량를 사용할 수 있다.The amount of the copolymer of the present invention may vary depending on organic solvents, photoacid generators, and lithography conditions, but is generally about 10 to 30 wt. Can be used.

본 발명에 따르는 공중합체를 사용하여 포토레지스트로 사용하는 방법을 보다 구체적으로 설명하면 다음과 같다.When using the copolymer according to the invention as a photoresist will be described in more detail as follows.

본 발명의 공중합체를 시클로헥사논에 10내지 30 중량로 용해시키고, 광산 발생제인 오니움염 또는 유기술폰산을 레지스트 고분자에 대해 0.2 내지 10 중량로 배합하고 초미세 필터로 여과하여, 포토레지스트 용액을 제조한다.10 to 30 weight of the copolymer of the present invention in cyclohexanone 0.2 to 10% by weight of the photoresist onium salt or euphonic acid based on the resist polymer The mixture was mixed with an ultrafine filter and filtered to prepare a photoresist solution.

그 다음 실리콘 웨이퍼에 스핀 도포하여 박막을 제조한 다음, 80내지 150의 오븐 또는 열판에서 1내지 5분간 소프트베이크를 하고, 원자외선 노광장치 또는 엑시머 레이져 노광장치를 이용하여 노광한 후, 100내지 200에서 노광후 베이크한다. 이렇게 노광한 웨이퍼를 2.38TMAH 수용액에서 1분30초간 침지함으로써 초미세 포지티브 레지스트 화상을 얻을 수 있게 된다.Next, spin-coating the silicon wafer to form a thin film, and then 80 to 150 Soft bake in an oven or hot plate at 1 to 5 minutes, and then exposed using an ultraviolet ray exposure apparatus or an excimer laser exposure apparatus, and then 100 to 200 Bake after exposure at The wafer thus exposed is 2.38 It is possible to obtain an ultrafine positive resist image by immersing in TMAH aqueous solution for 1 minute 30 seconds.

[실시예 1: 2-카르복실산-5-노보렌 단량체의 합성]Example 1: Synthesis of 2-carboxylic acid-5-norborene monomer

반응기에 시클로펜타디엔과 아크릴산을 동일한 몰비로 에틸에테르 용매에 녹인 다음, 약 20에서 24시간 반응시킨다. 반응 완료후 로타리 증류기로 용매를 제거한 다음, 감압 증류하여 엔도(endo)와 엑소(exo) 혼합물의 2-카르복실산-5-노보렌을 얻었다. 수율은 80이었다.In the reactor, cyclopentadiene and acrylic acid were dissolved in an ethyl ether solvent in the same molar ratio, and about 20 Reaction at 24 hours. After completion of the reaction, the solvent was removed using a rotary distiller, and then distilled under reduced pressure to obtain 2-carboxylic acid-5-novolene of an endo and exo mixture. Yield 80 It was.

[실시예 2: 2-t-부틸 카르복실레이트-5-노보렌의 합성]Example 2: Synthesis of 2-t-butyl carboxylate-5-norborene

반응기에 시클로펜타디엔과 t-부틸아크릴레이트를 동일한 몰비로 에틸에테르 용매에 녹인 다음, 20에서 24시간 반응시킨다. 반응 완료후 로터리 증류기로 용매를 제거한 다음, 감압 증류하여 엔도(endo)와 엑소(exo) 혼합물의 2-t-부틸카르복실레이트-5-노보렌을 얻었다. 수율은 78이었다.In the reactor, cyclopentadiene and t-butyl acrylate were dissolved in an ethyl ether solvent in the same molar ratio, and 20 Reaction at 24 hours. After completion of the reaction, the solvent was removed using a rotary distillation, followed by distillation under reduced pressure to obtain 2-t-butylcarboxylate-5-norborene of an endo and exo mixture. Yield 78 It was.

[실시예 3: 공중합체의 합성]Example 3: Synthesis of Copolymer

하기 화학식 3 에 도시된 바와 같이 실시예 1에서 합성한 2-카르복실산-5-노보렌, 실시예 2에서 합성한 2-t-부틸 카르복실레이트-5-노보렌, 비닐렌 카보네이트, 및 2-히드록시에틸아크릴레이트을 1: 1: 2: 1 의 몰비로 반응기에 넣고 THF용매에 녹인다. 여기에 AIBN 0.2 몰를 넣은 후, 반응기를 질소 분위기로 바꾸어준다. 온도를 65로 맞춘 후에서 10 시간 반응시킨다. 반응 완료후 로타리 증류기로 용매 일부를 제거한 다음, 에틸에테르에서 침전시킨 후, 침전물을 여과하여 진공오븐에 건조시켜, 건조된 생성물을 감광막 수지로 사용하였다.2-carboxylic acid-5-norborene synthesized in Example 1 as shown in the following formula (3), 2-t-butyl carboxylate-5-norborene synthesized in Example 2, vinylene carbonate, and 2-hydroxyethyl acrylate is added to the reactor in a molar ratio of 1: 1: 2: 1 and dissolved in a THF solvent. AIBN 0.2 mol here After the addition, the reactor is changed to a nitrogen atmosphere. Temperature to 65 After adjusting to 10 hours. After completion of the reaction, a part of the solvent was removed by rotary distillation, and then precipitated in ethyl ether. The precipitate was filtered and dried in a vacuum oven, and the dried product was used as a photoresist resin.

이상과 같이 본 발명에 따르는 신규한 공중합체를 사용한 포토레지스트는 에칭 내성 및 내열성이 우수하고, 2.38TMAH 수용액을 현상액으로 사용할 수 있을 뿐만 아니라, 접착성이 뛰어난 감광막을 제조할 수 있었다.As described above, the photoresist using the novel copolymer according to the present invention is excellent in etching resistance and heat resistance, and 2.38 Not only the aqueous TMAH solution could be used as a developer, but also a photosensitive film excellent in adhesiveness could be produced.

이상의 본 발명에 대한 상세한 설명 및 실시예는 예시의 목적을 위해 개시된 것이며, 당업자라면 본 발명의 사상과 범위 안에서 다양한 수정, 변경, 부가등이 가능할 것이고, 이러한 수정 변경 등은 이하의 특허 청구의 범위에 속하는 것으로 보아야 할 것이다.The above detailed description and embodiments of the present invention have been disclosed for purposes of illustration, and those skilled in the art will be able to make various modifications, changes, additions, and the like within the spirit and scope of the present invention. Should be seen as belonging to.

Claims (5)

(i) 제1공단량체로서, 하기 화학식 1의 2-히드록시에틸아크릴레이트 유도체와,(i) a first comonomer, 2-hydroxyethyl acrylate derivative represented by the following formula (1), (ii) 제2공단량체로서, 비닐렌 카르보네이트, 2-시클로펜텐-1-아세트산, 2-시클로펜텐-1-(t-부틸 아세테이트), 비시클로[2,2,2]옥트-5-엔-2-t-부틸 카르복실레이트, 비시클로[2,2,2]옥트-5-엔-2-카르복실산, 비시클로[2,2,2]옥트-5-엔-2-(2-히드록시에틸)카르복실레이트, 2-(2-하이드록시에틸)카르복실레이트-5-노르보넨, 2-t-부톡시 카르복실레이트-5-노르보넨, 2-카르복실산-5-노르보넨, 시클로펜텐, 시클로헥센, 노르보닐렌, 및 노르보닐렌-2-메탄올로 구성된 그룹에서 선택된 1 이상의 지방족 환형 올레핀 유도체 화합물을 포함하는 것을 특징으로 하는 신규한 포토레지스트 공중합체.(ii) As second comonomer, vinylene carbonate, 2-cyclopentene-1-acetic acid, 2-cyclopentene-1- (t-butyl acetate), bicyclo [2,2,2] oct-5 -Ene-2-t-butyl carboxylate, bicyclo [2,2,2] oct-5-ene-2-carboxylic acid, bicyclo [2,2,2] oct-5-ene-2- (2-hydroxyethyl) carboxylate, 2- (2-hydroxyethyl) carboxylate-5-norbornene, 2-t-butoxy carboxylate-5-norbornene, 2-carboxylic acid- A novel photoresist copolymer comprising at least one alicyclic olefin derivative compound selected from the group consisting of 5-norbornene, cyclopentene, cyclohexene, norbornylene, and norbornylene-2-methanol. 상기 식에서, R 은 수소 또는 메틸이다.Wherein R is hydrogen or methyl. 제1항에 있어서, 상기 공중합체는 하기 화학식 3의 화합물인 것을 특징으로 하는 포토레지스트 공중합체.The photoresist copolymer of claim 1, wherein the copolymer is a compound represented by the following Chemical Formula 3. 상기 식에서, x, y 및 z는 공중합체 관여하는 각 공단량체의 중합비이다.Wherein x, y and z are the polymerization ratios of each comonomer involved in the copolymer. 제1항에 있어서, 상기 공중합체의 분자량이 3,000 내지 200,000임을 특징으로 하는 공중합체.The copolymer according to claim 1, wherein the copolymer has a molecular weight of 3,000 to 200,000. (a) (i) 제1공단량체로서, 하기 화학식 1의 2-히드록시에틸아크릴레이트 유도체와, (ii) 제2공단량체로서, 비닐렌 카르보네이트, 2-시클로펜텐-1-아세트산, 2-시클로펜텐-1-(t-부틸 아세테이트), 비시클로[2,2,2]옥트-5-엔-2-t-부틸 카르복실레이트, 비시클로[2,2,2]옥트-5-엔-2-카르복실산, 비시클로[2,2,2]옥트-5-엔-2-(2-히드록시에틸)카르복실레이트, 2-(2-하이드록시에틸)카르복실레이트-5-노르보넨, 2-t-부톡시 카르복실레이트-5-노르보넨, 2-카르복실산-5-노르보넨, 시클로펜텐, 시클로헥센, 노르보닐렌, 및 노르보닐렌-2-메탄올로 구성된 지방족 환형 올레핀 유도체 그룹에서 선택된 1 이상의 화합물을 중합유기용매에 녹이는 단계와, (b) 상기 결과물 용액에 중합개시제를 첨가하여 공중합반응시키는 단계와, (c) 상기 결과물 용액을 침전 및 여과하는 단계를 포함하는 것을 특징으로 하는 포토레지스트 공중합체의 제조방법.(a) (i) as a first comonomer, a 2-hydroxyethyl acrylate derivative of the formula (1); (ii) as a second comonomer, vinylene carbonate, 2-cyclopentene-1-acetic acid, 2-cyclopentene-1- (t-butyl acetate), bicyclo [2,2,2] oct-5-ene-2-t-butyl carboxylate, bicyclo [2,2,2] oct-5 -En-2-carboxylic acid, bicyclo [2,2,2] oct-5-ene-2- (2-hydroxyethyl) carboxylate, 2- (2-hydroxyethyl) carboxylate- With 5-norbornene, 2-t-butoxy carboxylate-5-norbornene, 2-carboxylic acid-5-norbornene, cyclopentene, cyclohexene, norbornylene, and norbornylene-2-methanol Dissolving at least one compound selected from the group of aliphatic cyclic olefin derivatives composed in a polymerized organic solvent, (b) adding a polymerization initiator to the resultant solution for copolymerization, and (c) precipitating and filtering the resultant solution. Comprising Process for producing a photoresist copolymer according to claim. 상기 식에서, R은 수소 또는 메틸이다.Wherein R is hydrogen or methyl. (i) 제1항 기재의 포토레지스트 공중합체와, (ii) 광산발생제와, (iii) 혼합유기용매를 포함하는 것을 특징으로 하는 포토레지스트 조성물.A photoresist composition comprising (i) the photoresist copolymer according to claim 1, (ii) a photoacid generator, and (iii) a mixed organic solvent.
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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100400295B1 (en) * 1998-10-17 2004-02-14 주식회사 하이닉스반도체 Novel photoresist monomer and polymer and photoresist composition using the same
KR100425442B1 (en) * 1999-08-24 2004-03-30 삼성전자주식회사 Photosensitive polymer and chemically amplified photoresist composition containing the same
KR100445920B1 (en) * 1999-03-11 2004-08-25 인터내셔널 비지네스 머신즈 코포레이션 Photoresist compositions with cyclic olefin polymers and additive

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100557599B1 (en) * 1999-08-31 2006-03-10 주식회사 하이닉스반도체 Photoresist monomer having functional group generating radical by irradiation, polymer thereof and photoresist composition containing it

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100400295B1 (en) * 1998-10-17 2004-02-14 주식회사 하이닉스반도체 Novel photoresist monomer and polymer and photoresist composition using the same
KR100445920B1 (en) * 1999-03-11 2004-08-25 인터내셔널 비지네스 머신즈 코포레이션 Photoresist compositions with cyclic olefin polymers and additive
KR100425442B1 (en) * 1999-08-24 2004-03-30 삼성전자주식회사 Photosensitive polymer and chemically amplified photoresist composition containing the same

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