KR930008134B1 - Composition for sensitizer - Google Patents

Composition for sensitizer Download PDF

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KR930008134B1
KR930008134B1 KR1019900019268A KR900019268A KR930008134B1 KR 930008134 B1 KR930008134 B1 KR 930008134B1 KR 1019900019268 A KR1019900019268 A KR 1019900019268A KR 900019268 A KR900019268 A KR 900019268A KR 930008134 B1 KR930008134 B1 KR 930008134B1
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South Korea
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polymer binder
photosensitive resin
resin composition
developing
salted
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KR1019900019268A
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Korean (ko)
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KR920010357A (en
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이창황
윤호영
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동양나이론 주식회사
공정곤
동양 폴리에스터 주식회사
배도
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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
    • 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Graft Or Block Polymers (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Manufacturing Of Printed Circuit Boards (AREA)
  • Laminated Bodies (AREA)

Abstract

This new photosensitive resin composition has an advantage that strength of photocuring layer is good; developing is fast; and developing time and level is not so dependent on the variable developing condition. The photosensitive composition is composed of 20-60 wt.% terminal ethylene unsaturated compd; 30-70 wt.% polymer binder and salted polymer binder; and 0.1-10 wt.% photopolymerization initiator. The preparation method of salted polymer binder comprises; (A) adding 100g styrene maleic anhydride in 500 ml H2O; (B) adding 239.2 ml of 3 wt/v% NaOH solution and stirring at 40 deg.C for 3 hours; (C) drying in vacuum oven and washing with ethanol; and (D) after drying, getting styrene maleic anhydride salted by sodium.

Description

감광성 수지 조성물Photosensitive resin composition

본 발명은 감광성 수지 조성물에 관한 것이다. 좀더 상세하게는, 광경화막의 강도가 우수하며, 현상공정 중에서 현상속도가 빠르며, 현상조건이 변하더라도 현상시간 및 현상정도가 크게 변하지 않아 감광성 수지 적층체를 제조하기 위해서 제공되는 생산성 및 신뢰성이 우수한 감광성 수지 조성물에 관한 것이다.The present invention relates to a photosensitive resin composition. More specifically, the strength of the photocuring film is excellent, the developing speed is fast during the developing process, and the development time and degree of development do not change significantly even when the developing conditions change, so that the productivity and reliability provided for manufacturing the photosensitive resin laminate are excellent. It relates to a photosensitive resin composition.

감광성 수지 조성물은 평판 인쇄판, 수지 凸판, 인쇄회로 기판 등의 제조시 화상 형성재료로 사용될뿐만 아니라, 도료, 접착제를 제조하는경우에도 유용하다. 일반적으로 인쇄회로 기판 제조시 내식막을 형성하는 방법은 크게 두가지로 대별되는데 그 방법으로서, 실크 스크린(Silk Screen)법에 의해 동박 적층판(Copper Clad Laminate)의 상부에 인쇄하는 방법과 폴리에스터 필름층 및 광중합성수지층, 보호필름층으로 형성된 적층체로부터 보호필름층을 벗겨낸 다음 동박적층판 위에, 상기 보호 필름층을 제거한 적층체의 광중합성 수지층을 적층시킨 후, 자외선에 의해 화상을 형성시키고 이어서 현상액을 이용하여 미반응 부분을 제거하므로써 내식막을 형성하는 방법이 있다.The photosensitive resin composition is not only used as an image forming material in manufacturing flat printing plates, resin plates, printed circuit boards, etc., but is also useful in producing paints and adhesives. Generally, a method of forming a resist when manufacturing a printed circuit board is roughly divided into two methods. The method of printing on a copper clad laminate by a silk screen method, a polyester film layer, The protective film layer is peeled off from the laminate formed of the photopolymerizable resin layer and the protective film layer, and then the photopolymerizable resin layer of the laminate from which the protective film layer is removed is laminated on the copper-clad laminate, and then an image is formed by ultraviolet rays, followed by a developer. There is a method of forming a resist by removing the unreacted portion using.

내식막이 형성된 기판을 에칭(Etching) 및 도금(Plating)에 의해 인쇄회로 기판의 회로를 형성한 후 내식막을 벗겨낸다. 감광성 필름을 사용할 경우 작업성 및 신뢰성 향상은 현상공정중에서 결정되는데 특히 현상시간이 빨라야 하며, 미반응 부분은 완전히 제거되고 경화막은 우수한 강도를 보유하는 현상특성을 나타내어야 한다.After forming the circuit of the printed circuit board by etching and plating the substrate on which the resist is formed, the resist is peeled off. When the photosensitive film is used, workability and reliability improvement are determined during the development process. In particular, development time should be fast, and unreacted parts should be completely removed and the cured film should exhibit development characteristics having excellent strength.

종래의 경우, 감광성 수지 조성물의 구성 물질중 광중합성물질로서는 말단 에틸렌성 불포화기를 적어도 1개 이상 가지는 화합물, 예를 들어, 트리메티롤 프로판 트리아크릴레이트, 트리메티롤 프로판디메티크릴레이트, 펜타에리트릴롤 트리아크릴레이트, 디펜타에리트리롤 헥사크릴레이트, 1, 6-헥산디올디 아크릴레이트, 2, 2'-비스[4-아크릴옥시-폴리에톡시)페닐] 프로판, 테트라 메티롤메탄 트리아크릴레이트, 테트라메티롤메탄 테트라 아크릴레이트, 디에틸렌 글리콜 디아크릴레이트, 트리프로필렌 디아크릴레이트, 1, 6-헥산디올 디아크릴레이트, 1, 5-펜탄디올 디아크릴레이트, 부틸프탈레이트, 글리세롤 트리아세테이트, 트리메티롤 프로판 트리아세테이트 등을 포함한다.Conventionally, as a photopolymerizable material among the constituent materials of the photosensitive resin composition, a compound having at least one terminal ethylenically unsaturated group, for example, trimethol propane triacrylate, trimethol propane dimethacrylate, pentaery Trilrol Triacrylate, Dipentaerytriol Hexaacrylate, 1, 6-hexanedioldiacrylate, 2, 2'-bis [4-acryloxy-polyethoxy) phenyl] propane, tetramethyrrolmethane tri Acrylate, tetrametholmethane tetra acrylate, diethylene glycol diacrylate, tripropylene diacrylate, 1, 6-hexanediol diacrylate, 1, 5-pentanediol diacrylate, butylphthalate, glycerol triacetate And trimethyrol propane triacetate.

상기의 광중합성 물질을 지지하여 필름상으로 만들어 줄 수 있는 고분자 결합제로는 예를 들어 폴리메틸 메타크릴레이트, 폴리스티렌 등의 비닐중합체, 또는 아크릴산, 아크릴산메틸, 메틸 메타아크릴레이트, 아크릴산 부틸, 스티렌, 메타크릴산 2-하이드록시 에틸, 아크릴로 니트린, 부타디엔, 에틸 아크릴레이트, 말레익 안하이드라이드 등의 공중합성분을 가지는 비닐공중합체, 또는 에폭시 수지, 키실렌 수지, 방향족 술폰아미도 포름알데히드 수지 등을 들 수 있다.Polymeric binders capable of supporting the above photopolymerizable material into a film form include, for example, vinyl polymers such as polymethyl methacrylate and polystyrene, or acrylic acid, methyl acrylate, methyl methacrylate, butyl acrylate, styrene, Vinyl copolymer having copolymerization components such as 2-hydroxyethyl methacrylate, acrylonitrile, butadiene, ethyl acrylate, maleic anhydride, or epoxy resin, xylene resin, aromatic sulfonamido formaldehyde resin Etc. can be mentioned.

광중합 개시제로는 벤조페논, 클로로벤조 페논, 4, 4'-디메틸아미노 벤조페논, 4, 4'-디에틸 아미노 벤조페논, 4, 4'-디클로로벤조 페논 등의 벤조 페논류, 또는, 2-에틸 안트라퀴논, 2-t-부틸 안트라퀴논 등의 안트라 퀴논류, 또는 벤조인 에틸에테르, 벤조인 이소프로필 에테르, 벤질 등의 1종 또는 2종이 사용되었다.Examples of the photopolymerization initiator include benzophenones such as benzophenone, chlorobenzophenone, 4, 4'-dimethylamino benzophenone, 4, 4'-diethyl amino benzophenone and 4, 4'-dichlorobenzophenone, or 2- Anthraquinones, such as ethyl anthraquinone and 2-t-butyl anthraquinone, or 1 type, or 2 types, such as benzoin ethyl ether, benzoin isopropyl ether, benzyl, were used.

이밖의 첨가물로는 벤조 이미다졸, 벤즈티아졸, 벤즈티옥사졸, 벤조트리아졸, 2-머캡토 벤즈티아졸, 2-머캡토 벤조 이미다졸 등의 접착촉진제와 감광성 수지 조성물의 저장안정성 및 코팅액 건조시 또는 라미네이션(Lamination) 시의 열 중합방지를 위한 하이드로 퀴논, p-메톡시 페놀, 2-하이드록시 벤조페논 등의 열중합 방지제, 루이코 계통의 메틸 바이오렛, 에틸바이오렛, 크리스탈 바이오렛 염료 등의 첨가제가 사용되어 왔다.Other additives include storage accelerators and coating liquids for adhesion promoters and photosensitive resin compositions such as benzoimidazole, benzthiazole, benzthioxazole, benzotriazole, 2-mercapto benzthiazole, and 2-mercapto benzo imidazole. Thermal polymerization inhibitors such as hydroquinone, p-methoxy phenol and 2-hydroxy benzophenone to prevent thermal polymerization during drying or lamination; Additives such as dyes have been used.

상기의 감광성 수지 조성물의 각 구성물질 첨가량은 광중합성층의 전체 무게에 대하여, 에틸렌성 불포화 화합물이 20 내지 60중량%, 고분자 결합제가 30 내지 70중량%, 광중합 개시제가 0.1 내지 10중량%의 것이 통상적이다. 그러나 이미 언급한 종래의 고분자 결합제 및 광중합성 물질만으로 감광성 수지 조성물을 제조할 경우에는 PCB 제조공정 적용시 노광에 의한 화상 형성후 1%의 Na2CO3수용액을 사용하여 미반응 감광층을 제거하는 현상공정에서 미 반응 부분이 완전이 제거되는데 걸리는 시간이 길어지는 단점을 보이고 있는 이는 PCB제조공정의 생산성 저하를 가져온다.The amount of each constituent added to the photosensitive resin composition is usually 20 to 60% by weight of the ethylenically unsaturated compound, 30 to 70% by weight of the polymer binder, and 0.1 to 10% by weight of the photopolymerization initiator, based on the total weight of the photopolymerizable layer. to be. However, when the photosensitive resin composition is manufactured using only the above-mentioned conventional polymer binder and photopolymerizable material, an unreacted photosensitive layer is removed by using a 1% Na 2 CO 3 aqueous solution after image formation by exposure in the PCB manufacturing process. This shows the disadvantage that the time taken for the complete removal of the unreacted portion in the developing process is long, which leads to a decrease in productivity of the PCB manufacturing process.

한편 기종의 감광성 수지 조성물로는 현상액의 압력이 1.2∼1.8kgt/cm2, 현상액의 온도가 28∼32℃의 조건하에서 작업을 해주어야 하며 상기 조건이 변할시 현상시간의 변화는 물론 경화막의 가까운 부분에 미 현상이 발생하여 추후 PCB제조공정중에 도금이 안되는 등 작업 신뢰성에 큰 문제점이 발생한다.On the other hand, the photosensitive resin composition of the type should be operated under the conditions of the pressure of the developing solution is 1.2 ~ 1.8kgt / cm 2 , the temperature of the developing solution is 28 ~ 32 ℃, the change of the development time when the conditions change, as well as the close part of the cured film There is a big problem in the reliability of work, such as the phenomenon that the phenomena occurs and plating is not possible during the PCB manufacturing process.

따라서 본 발명은 상기의 현상조건에서 현상시간을 단축시킬 수 있으며 현상조건이 변하더라도 현상시간이 크게 변하지 않으며 완벽한 현상이 될수 있는 감광성 수지 조성물의 제공에 관한 것이다.Therefore, the present invention relates to the provision of the photosensitive resin composition which can shorten the development time under the above-described development conditions, and the development time does not change greatly even when the development conditions are changed.

본 발명자는 우선 현상공정의 메카니즘을 주의깊게 연구하여 현상의 원리는 감광성 조성물중에서 필름을 형성하는 고분자 결합제의 유기 카르복실산과 염기성 현상액의 중화반응으로 결과됨을 알게 되었다. 그리고 아크릴 삼원중합체나 스티렌 말레익 안하이드라이드 수지와 같은 고분자 결합제는 일반적으로 물에 녹지 않으나 알카리 수산화나트륨이나 수산화 암모늄을 가하면 염이 형성되고 염화된 고분자 결합제는 물에 녹는다. 따라서 감광성 수지 조성물중 염화된 고분자 결합제를 첨가함으로써 현상시간의 단축 및 현상특성의 향상을 얻을수 있어 생산성 향상 및 제조원가 절감을 도모할 수 있다. 염화된 고분자를 만드는 방법으로 100gr의 스티렌 말레익 안하이드라이드(상품명 : Scripset 550)를 500ml H2O에 넣는다.The inventors first carefully studied the mechanism of the developing process and found that the principle of development is the result of the neutralization reaction of the basic developer with the organic carboxylic acid of the polymeric binder forming the film in the photosensitive composition. In addition, polymer binders such as acrylic terpolymers and styrene maleic anhydride resins are generally insoluble in water, but salts are formed when alkali sodium hydroxide or ammonium hydroxide is added, and chlorinated polymer binders are dissolved in water. Therefore, the addition of the chlorinated polymer binder in the photosensitive resin composition can shorten the development time and improve the development characteristics, thereby improving productivity and reducing manufacturing costs. To make a chlorinated polymer, 100 gr of styrene maleic anhydride (trade name: Scripset 550) is added to 500 ml H 2 O.

박리시와 유사한 환경을 만들기 위해 용매로 물을 사용하였으며 이때 중합체는 물에 녹지 않는 상태에 있다. 여기에 NaOH 3wt/v% 수용액 239.2ml를 넣고 40℃에서 3시간 교반한다.Water was used as a solvent to create an environment similar to that at the time of stripping, wherein the polymer is insoluble in water. 239.2ml of NaOH 3wt / v% aqueous solution was added thereto and stirred at 40 ° C for 3 hours.

교반후 용액이 투명하게 되면 물을 진공오븐에서 건조한 후, 미반응 NaOH를 제거하기 위해 에탄올로 세척한 다음 다시 건조하여 Na로 염화된 스티렌 말레익 안하이드라이드를 얻는다. 같은 방법으로 아크릴 삼원중합체(상품명 : Carboset 525, Carboset N-27)을 증류수에 넣은 후 NaOH 수용액을 첨가 후 교반하고 같은 방법으로 하며 Na로 염화된 아크릴 삼원중합체를 얻는다.When the solution becomes clear after stirring, the water is dried in a vacuum oven, washed with ethanol to remove unreacted NaOH, and then dried again to obtain styrene maleic anhydride, which is chlorided with Na. In the same manner, the acrylic terpolymer (trade name: Carboset 525, Carboset N-27) is added to distilled water, followed by stirring after adding an aqueous NaOH solution.

이하에 실시예를 통하여 본 발명을 보다 설명한다.Hereinafter, the present invention will be described through examples.

[실시예 1, 2, 3, 비교예 1, 2][Examples 1, 2, 3, Comparative Examples 1, 2]

[조성예][Composition example]

상기 각 실시예에 따라 조성물을 조성하고 이를 교반기를 이용하여 충분히 혼합후 25㎛ 두께의 폴리에틸렌 테레프탄레이트 필름 위에 도포하고 80∼130℃ 건조기에서 10분간 건조하여 용액 MEK를 휘발시켜 감광성 필름을 얻는다. 이 필름의 감광층을 동박적층판(Copper Clad Laminate) 위에 적층시킨 후 자외선에 의해 화상을 형성시킨다. 이어서 28℃의 1wt/v%의 Na2CO3수용액을 사용하여 샤워(Shower) 스프레이 압력 1.5kgt/cm2로 감광층을 현상하고, 미 노광된 부분의 감광층이 완전히 없어질때까지의 시간을 측정하였다. 한편 온도 및 스프레이 압력을 변화시켰을 때의 현상시간도 아울러 측정하여 그 결과를 표 1에 나타내었다.The composition was prepared according to each of the above examples, and the mixture was sufficiently mixed using a stirrer, and then coated on a 25 μm-thick polyethylene terephthalate film and dried for 10 minutes in an 80-130 ° C. dryer to volatilize the solution MEK to obtain a photosensitive film. . The photosensitive layer of this film is laminated on a copper clad laminate, and an image is formed by ultraviolet rays. Subsequently, the photosensitive layer was developed at a shower spray pressure of 1.5 kgt / cm 2 using a 1 wt / v% Na 2 CO 3 aqueous solution at 28 ° C., and the time until the photosensitive layer of the unexposed part disappeared was completely removed. Measured. On the other hand, the development time at the time of changing the temperature and spray pressure was also measured, and the result is shown in Table 1.

[표 1]TABLE 1

비교예 2의 경우 현상액에 대한 반응성이 너무 좋아 미 반응 부분은 물론 반응된 경화막도 일부 현상액에 반응하여 없어져 버리는 불량현상을 보였다.In Comparative Example 2, the reactivity with the developing solution was so good that not only the unreacted portion but also the reacted cured film reacted with some of the developing solution.

[실시예 4, 5, 6 비교예 3, 4][Examples 4, 5, 6 Comparative Examples 3, 4]

하기의 조성성분을 사용하여 실시예 1과 같이 실험 후 그 결과를 표 2에 나타내었다.After the experiment as in Example 1 using the following composition components are shown in Table 2.

[표 2]TABLE 2

비교예 4의 경우 현상액에 대한 반응성이 너무 좋아 미 반응 부분은 물론 반응된 경화막도 일부 현상액에 반응하여 없어져 버리는 불량현상을 보였다.In Comparative Example 4, the reactivity with the developing solution was so good that not only the unreacted portion but also the reacted cured film reacted with some of the developing solution.

Claims (3)

(A) 분자량 500이하인 말단에틸렌성 불포화 화합물 20 내지 60중량% (B) 고분자 결합제 및 염화된 고분자 결합제 30 내지 70중량%, (C) 광중합 개시제 0.1 내지 10중량%로 주로 조성되는 것을 특징으로한 감광성 수지 조성물.(A) 20 to 60% by weight of terminal ethylenically unsaturated compounds having a molecular weight of 500 or less (B) 30 to 70% by weight of polymer binders and chlorinated polymer binders, and (C) 0.1 to 10% by weight of photopolymerization initiators. Photosensitive resin composition. 제 1 항에 있어서, 상기 염화된 고분자 결합제는 Na로 염화된 고분자 결합제인 것을 특징으로 하는 감광성 수지 조성물.The photosensitive resin composition of claim 1, wherein the chlorinated polymer binder is a polymer binder chlorinated with Na. 제 1 항에 있어서, 상기 염화된 고분자 결합제는 전체 고분자 결합제에 대하여 20 내지 80중량%로 조성되는 것을 특징으로 하는 감광성 수지 조성물.The photosensitive resin composition of claim 1, wherein the chlorinated polymer binder is comprised in an amount of 20 to 80 wt% based on the total polymer binder.
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