KR20130063172A - Polyimide photosensitive composition for lazer induced thermal imaging - Google Patents
Polyimide photosensitive composition for lazer induced thermal imaging Download PDFInfo
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Abstract
Description
본 발명은 레이저 열전사용 폴리이미드 감광성 조성물에 관한 것으로, 보다 상세하게는 기판과의 접착력이 뛰어난 물질을 사용함으로써 레이저 열전사법(laser induced thermal imaging, LITI)에 적용시 이중 테이퍼 형성이 가능하고, 이형성이 우수한 폴리이미드 감광성 조성물에 관한 것이다.
The present invention relates to a laser thermal transfer polyimide photosensitive composition, and more particularly, by using a material having excellent adhesion to a substrate, double taper formation is possible when applied to laser induced thermal imaging (LITI), It is related with this excellent polyimide photosensitive composition.
일반적으로, 평판표시소자(Flat Panel Display Device) 중에서, 유기 발광표시소자(OLED)는 절연기판 상에 하부 전극인 애노드 전극이 형성되고, 애노드 전극 상에 절연막을 포함하는 유기막층이 형성되며, 유기막층 상에 상부 전극인 캐소드 전극이 형성된다. 유기막층은 정공주입층, 정공수송층, 발광층, 정공억제층, 전자수송층, 전자주입층 중 적어도 하나를 포함한다. 유기 발광 소자는 복수 개의 화소를 구비하고 각 화소를 한정하고 전극의 단락 및 각 층간의 평탄화 등을 위하여 절연막(Pixel Defined Layer)을 포함한다. 절연막으로는 유기물 및 무기물이 사용될 수 있다.In general, among flat panel display devices, an organic light emitting diode (OLED) includes an anode electrode, which is a lower electrode, formed on an insulating substrate, and an organic film layer including an insulating layer formed on the anode electrode. The cathode electrode which is the upper electrode is formed on the film layer. The organic layer includes at least one of a hole injection layer, a hole transport layer, a light emitting layer, a hole suppression layer, an electron transport layer, an electron injection layer. The organic light emitting diode includes a plurality of pixels, defines each pixel, and includes an insulating layer for shorting electrodes and planarization between layers. Organic and inorganic materials may be used as the insulating film.
상기 절연막을 무기물을 사용하여 형성하는 경우, 막 자체의 견고성이 뛰어나 상기 유기발광층의 전사 후 도너 기판의 전사층 제거시 잘 뜯겨나가지 않으며, 얇은 두께로 적층할 수 있다는 장점이 있다. 그러나 상기 무기물은 비어홀 내부를 충전하는 능력이 취약할 뿐 아니라, 막의 두께를 증가시킬 경우 스트레스로 인하여 비어홀 주변 및 제 1 전극의 돌출된 외곽부분에서 크랙을 발생시켜 제 1 전극과 제 2 전극 간에 쇼트가 발생할 우려가 있다.When the insulating film is formed by using an inorganic material, the film itself has excellent rigidity, and thus, when the transfer layer of the donor substrate is removed after transfer of the organic light emitting layer, the insulating layer may be laminated to a thin thickness. However, the inorganic material not only has a weak ability to fill the via hole, but also increases the thickness of the film, causing cracks around the via hole and protruding outer portions of the first electrode due to stress, resulting in a short circuit between the first electrode and the second electrode. There is a risk of occurrence.
또한 일반적인 유기물을 사용하여 절연막을 형성하는 경우, 상기 절연막을 형성하는데 있어 화소를 한정하도록 개구를 형성하기 위해서 포토 리소그래피법 및 습식 식각에 의한 패터닝을 하게 되면 유기물인 발광층에 손상을 줄 수 있다.In addition, when an insulating film is formed using a general organic material, patterning by photolithography and wet etching to form an opening to define a pixel in forming the insulating film may damage the organic light emitting layer.
이에, 상기 절연막을 형성하는 방법의 하나로 레이저 열전사법(laser induced thermal imaging, LITI)을 들 수 있는데, 이는 레이저에서 나온 빛을 열에너지로 변환하고, 변환된 열에너지에 의해 전사층을 유기 발광표시장치의 기판으로 전사시켜 유기막층을 형성하는 방법이다. 레이저 열전사 방법은 레이저로 유도된 이미징 프로세스로 고해상도의 패턴 형성 및 균일한 두께의 필름을 제조할 수 있을 뿐 아니라, 필름을 밀착시키기 때문에 정렬 정밀도가 매우 높으며, 다층 형성이 가능하고, 레이저빔 크기에 따라 소형 기판의 초미세 패턴으로부터 대형 기판의 균일한 화소형성 패턴에 까지 대응이 용이하다.Accordingly, one method of forming the insulating layer may be laser induced thermal imaging (LITI), which converts light emitted from a laser into thermal energy, and converts the transfer layer into an organic light emitting display device by the converted thermal energy. It is a method of forming an organic film layer by transferring to a board | substrate. The laser thermal transfer method is not only able to produce high-resolution pattern formation and uniform thickness film by laser-induced imaging process, but also very high alignment accuracy, multi-layer formation, and laser beam size due to the adhesion of the film. Accordingly, it is easy to cope from the ultrafine pattern of the small substrate to the uniform pixel formation pattern of the large substrate.
종래에 레이저 열전사법을 사용하여 절연막을 형성하는 경우 유기물로서 폴리이미드 계열의 수지가 사용되었으나, 종래의 일반적인 폴리이미드 조성물을 LITI에 적용할 경우, 이중 테이퍼 형성이 불가능하여 공정 마진이 떨어지는 단점이 있다.Conventionally, a polyimide-based resin is used as an organic material when forming an insulating film by using a laser thermal transfer method. However, when a conventional general polyimide composition is applied to LITI, a double taper cannot be formed, resulting in a poor process margin. .
따라서 종래 유기 절연막의 단점을 보완할 수 있는 신규한 조성물이 요구되고 있다.
Therefore, there is a need for a novel composition that can compensate for the disadvantages of the conventional organic insulating film.
상기와 같은 문제점을 해결하기 위해, 본 발명은 LITI 공법 적용시 이중 테이퍼 형성이 가능한 폴리이미드 감광성 조성물을 제공하는 것을 목적으로 한다.In order to solve the above problems, an object of the present invention is to provide a polyimide photosensitive composition capable of forming a double taper when applying the LITI method.
본 발명은 또한 상기 레이저 열전사용 폴리이미드 감광성 조성물을 이용하여 제조된 절연막 및 이를 포함하는 유기 발광 표시 소자(OLED)를 제공하는 것을 목적으로 한다.
Another object of the present invention is to provide an insulating film manufactured by using the polyimide photosensitive composition for laser thermal transfer and an organic light emitting display device (OLED) including the same.
상기 목적을 달성하기 위해 본 발명은 폴리이미드 전구체, 하이드록시스티렌 고분자, PAC(photo active compound) 및 용매를 포함하며, 상기 폴리이미드 전구체가 다이아민(diamine)계 단량체로서 1,3-비스(3-아미노프로필)테트라메틸다이실록산(SiDA)을 포함하거나, 아민계 단량체로서 N-2(아미노에틸)3-아미노프로필트라이메톡시실란(KBM-603)을 포함하거나, 또는 protecting group로서 (3-글리시딜옥시프로필)트라메톡시실란(GPTS)을 포함하는 것을 특징으로 하는 레이저 열전사용 폴리이미드 감광성 조성물을 제공한다.
To achieve the above object, the present invention includes a polyimide precursor, a hydroxystyrene polymer, a photo active compound (PAC), and a solvent, wherein the polyimide precursor is a 1,3-bis (3) as a diamine monomer. -Aminopropyl) tetramethyldisiloxane (SiDA) or N-2 (aminoethyl) 3-aminopropyltrimethoxysilane (KBM-603) as amine monomer or as a protecting group (3- It provides a polyimide photosensitive composition for laser thermal transfer, comprising glycidyloxypropyl) trimethoxysilane (GPTS).
또한 본 발명은 상기 폴리이미드 감광성 조성물을 이용하여 제조된 절연막을 제공한다.
In another aspect, the present invention provides an insulating film prepared using the polyimide photosensitive composition.
또한 본 발명은 상기 절연막을 포함하는 유기 발광 소자를 제공한다.
In another aspect, the present invention provides an organic light emitting device comprising the insulating film.
본 발명의 폴리이미드 감광성 조성물은 레이저 열전사법(laser induced thermal imaging, LITI)에 적용시 이중 테이퍼 형성이 가능하고, 이형성이 우수하므로, 절연막(Pixel Defined Layer) 및 이를 포함하는 유기 발광 표시 소자에 유용하게 사용될 수 있다.
Since the polyimide photosensitive composition of the present invention is capable of double taper formation and excellent releasability when applied to laser induced thermal imaging (LITI), it is useful for an insulating film and an organic light emitting display device including the same. Can be used.
도 1은 레이저 전사공정의 개략도이다.1 is a schematic diagram of a laser transfer process.
본 발명은 LITI 공법 적용시 이중 테이퍼 형성이 가능한 폴리이미드 감광성 조성물에 관한 것이다.
The present invention relates to a polyimide photosensitive composition capable of double tapering upon application of the LITI method.
이하, 본 발명을 상세히 설명한다.
Hereinafter, the present invention will be described in detail.
본 발명의 레이저 전사용 폴리이미드 감광성 조성물은 폴리이미드 전구체, 하이드록시스티렌 고분자, PAC(photo active compound) 및 용매를 포함하며, 상기 폴리이미드 전구체가 다이아민(diamine)계 단량체로서 1,3-비스(3-아미노프로필)테트라메틸다이실록산(SiDA)을 포함하거나, 아민계 단량체로서 N-2(아미노에틸)3-아미노프로필트라이메톡시실란(KBM-603)을 포함하거나, 또는 protecting group로서 (3-글리시딜옥시프로필)트라메톡시실란(GPTS)을 포함하는 것을 특징으로 한다.
The polyimide photosensitive composition for laser transfer of the present invention comprises a polyimide precursor, a hydroxystyrene polymer, a photo active compound (PAC) and a solvent, wherein the polyimide precursor is a 1,3-bis as a diamine monomer. (3-aminopropyl) tetramethyldisiloxane (SiDA), N-2 (aminoethyl) 3-aminopropyltrimethoxysilane (KBM-603) as an amine monomer, or as a protecting group ( 3-glycidyloxypropyl) trimethoxysilane (GPTS).
바람직하게, 상기 폴리이미드 감광성 조성물은,Preferably, the polyimide photosensitive composition,
(1) 상기 폴리이미드 전구체 20 내지 40 중량부;(1) 20 to 40 parts by weight of the polyimide precursor;
(2) 하이드록시스티렌 고분자 10 내지 20 중량부;(2) 10 to 20 parts by weight of hydroxystyrene polymer;
(3) PAC 화합물 3 내지 20 중량부; 및 (3) 3 to 20 parts by weight of PAC compound; And
(4) 용매 70 내지 90 중량부를 포함하는 것을 특징으로 한다.(4) It is characterized by including 70-90 weight part of solvents.
이하 각 성분들에 대하여 설명한다.
Each component is demonstrated below.
(1) 폴리이미드 전구체(1) polyimide precursor
폴리이미드 전구체는 아민계 또는 다이아민계 단량체 성분과 이무수물 성분을 극성 유기용매 내에서 2단계 축중합시키고, 말단에 protecting group를 결합시켜 제조되며, 본 발명에 있어서 폴리이미드 전구체는 상기 다이아민(diamine)계 단량체로서 1,3-비스(3-아미노프로필)테트라메틸다이실록산(SiDA)을 포함하거나, 아민계 단량체로서 N-2(아미노에틸)3-아미노프로필트라이메톡시실란(KBM-603)을 포함하거나, 또는 protecting group로서 (3-글리시딜옥시프로필)트라메톡시실란(GPTS)을 포함하는 것을 특징으로 한다. The polyimide precursor is prepared by condensation polymerization of an amine-based or diamine-based monomer component with a dianhydride component in a polar organic solvent in two stages, and by attaching a protecting group to a terminal thereof. 1) -bis (3-aminopropyl) tetramethyldisiloxane (SiDA) as the monomeric monomer or N-2 (aminoethyl) 3-aminopropyltrimethoxysilane (KBM-603) as the amine monomer Or (3-glycidyloxypropyl) tramethoxysilane (GPTS) as a protecting group.
바람직하기로 상기 폴리이미드 전구체는 하기 화학식 1로 표시되는 폴리이미드 전구체인 것이 좋다.Preferably, the polyimide precursor is a polyimide precursor represented by the following formula (1).
[화학식 1][Formula 1]
상기 화학식 1에서, In Formula 1,
X는 4가의 유기기이며, Y는 일부 또는 전체가 1,3-비스(3-아미노프로필)테트라메틸다이실록산(SiDA) 또는 N-2(아미노에틸)3-아미노프로필트라이메톡시실란(KBM-603)인 유기기이며, R은 각각 독립적으로 에폭시 사이클로헥실 메틸 메타크릴레이트(ECMMA) 또는 (3-글리시딜옥시프로필)트라메톡시실란(GPTS)이며, n은 3 내지 100,000의 정수이다. 상기에서 Y 중 3-50 몰%가 1,3-비스(3-아미노프로필)테트라메틸다이실록산(SiDA) 또는 N-2(아미노에틸)3-아미노프로필트라이메톡시실란(KBM-603)로 유도된 유기기인 것이 좋으며, R은 에폭시 사이클로헥실 메틸 메타크릴레이트(ECMMA):(3-글리시딜옥시프로필)트라이메톡시실란(GPTS)의 비율이 몰비로 80-99:1-20인 것이 좋다.X is a tetravalent organic group, Y is partially or totally 1,3-bis (3-aminopropyl) tetramethyldisiloxane (SiDA) or N-2 (aminoethyl) 3-aminopropyltrimethoxysilane (KBM -603), R is independently epoxy cyclohexyl methyl methacrylate (ECMMA) or (3-glycidyloxypropyl) tramethoxysilane (GPTS), and n is an integer from 3 to 100,000 . Wherein 3-50 mole% of Y is converted to 1,3-bis (3-aminopropyl) tetramethyldisiloxane (SiDA) or N-2 (aminoethyl) 3-aminopropyltrimethoxysilane (KBM-603) It is preferred that the organic group is derived, and R is an epoxy cyclohexyl methyl methacrylate (ECMMA) :( 3-glycidyloxypropyl) trimethoxysilane (GPTS) in a molar ratio of 80-99: 1-20. good.
더욱 바람직하기로 상기 X는 2,2-비스(3,4-안하이드로다이카복시페닐)헥사플루오로프로판(6FDA), 5-(2,5-다이옥소테트라하이드로퓨릴)-3-메틸-3-사이클로헥센-1,2-다이카복실산 무수물(DOCDA), 또는 2,3,3',4'-바이페닐 테트라카복실산 이무수물(a-BPDA)으로부터 유도된 4가의 유기기이며, 상기 Y 중 일부는 4,4'-다이아미노-3,3'-다이메틸-다이페닐메탄(DADM) 또는 2,2-비스(3-아미노-4-하이드록시페닐)-헥사플루오로프로판(Bis-APAF)으로부터 유도된 2가의 유기기인 것이 좋다.More preferably, X is 2,2-bis (3,4-anhydrodicarboxyphenyl) hexafluoropropane (6FDA), 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3 A tetravalent organic group derived from -cyclohexene-1,2-dicarboxylic acid anhydride (DOCDA), or 2,3,3 ', 4'-biphenyl tetracarboxylic dianhydride (a-BPDA), wherein some of said Y Is 4,4'-diamino-3,3'-dimethyl-diphenylmethane (DADM) or 2,2-bis (3-amino-4-hydroxyphenyl) -hexafluoropropane (Bis-APAF) It is preferable that it is a divalent organic group derived from.
본 발명에서 상기 폴리이미드 전구체의 분자량은 3,000-10,000인 것이 좋으며, 바람직하기로는 3,500-7,000인 것이 좋다. 상기 범위 내인 경우 용해도 조절, 수율 및 감도를 더욱 증진시킬 수 있다. In the present invention, the molecular weight of the polyimide precursor is preferably 3,000-10,000, preferably 3,500-7,000. If it is in the above range, solubility control, yield and sensitivity can be further enhanced.
또한 본 발명에서 상기 폴리이미드 고분자 제조에 사용되는 용매의 종류는 본 발명이 속하는 기술분야에서 통상적으로 사용되는 용매를 사용할 수 있다. In addition, in the present invention, the solvent used for preparing the polyimide polymer may be a solvent that is commonly used in the art to which the present invention pertains.
본 발명에서 상기 폴리이미드 고분자의 함량은 20-40 중량부로 사용하는 것이 좋으며, 상기 범위 내인 경우 내열성을 더욱 증진시킬 수 있다.
In the present invention, the content of the polyimide polymer is preferably used in an amount of 20-40 parts by weight, and if it is within the above range, it may further improve heat resistance.
(2) 하이드록시스티렌 고분자(2) hydroxystyrene polymer
본 발명에서는 상기 하이드록시스티렌 고분자는 분자량이 4,000 내지 20,000인 것을 사용하는 것이 좋고, 함량은 10-20 중량부로 사용하는 것이 좋으며, 상기 범위 내인 경우 내열성을 더욱 증진시킬 수 있다.
In the present invention, the hydroxystyrene polymer is preferably used that has a molecular weight of 4,000 to 20,000, the content is preferably used in 10-20 parts by weight, it can further enhance the heat resistance in the above range.
(3) PAC(3) PAC
본 발명에 사용되는 상기 PAC은 OLED 절연막에 사용될 수 있는 공지의 PAC가 적용될 수 있으며, 본 발명에 있어서 상기 PAC는 3-20 중량부로 포함되는 것이 바람직하다.
The PAC used in the present invention may be a known PAC that can be used for the OLED insulating film, and in the present invention, the PAC is preferably included in an amount of 3-20 parts by weight.
(4) 용매(4) Solvent
본 발명에서는 당분야에서 폴리이미드 감광성 조성물 제조를 위해 사용하는 통상적인 용매를 사용할 수 있으며, 구체적으로는 메탄올, 에탄올, 벤질알코올, 헥실알코올 등의 알코올류; 에틸렌글리콜메틸에테르아세테이트, 에틸렌글리콜에틸에테르아세테이트 등의 에틸렌글리콜알킬에테르아세테이트류; 에틸렌글리콜메틸에테르프로피오네이트, 에틸렌글리콜에틸에테르프로피오네이트 등의 에틸렌글리콜알킬에테르프로피오네이트류; 에틸렌글리콜메틸에테르, 에틸렌글리콜에틸에테르 등의 에틸렌글리콜모노알킬에테르류; 디에틸렌글리콜모노메틸에테르, 디에틸렌글리콜모노에틸에테르, 디에틸렌글리콜디메틸에테르, 디에틸렌글리콜메틸에틸에테르 등의 디에틸렌글리콜알킬에테르류; 프로필렌글리콜메틸에테르아세테이트, 프로필렌글리콜에틸에테르아세테이트, 프로필렌글리콜프로필에테르아세테이트 등의 프로필렌글리콜알킬에테르아세테이트류; 프로필렌글리콜메틸에테르프로피오네이트, 프로필렌글리콜에틸에테르프로피오네이트, 프로필렌글리콜프로필에테르프로피오네이트 등의 프로필렌글리콜알킬에테르프로피오네이트류; 프로필렌글리콜메틸에테르, 프로필렌글리콜에틸에테르, 프로필렌글리콜프로필에테르, 프로필렌글리콜부틸에테르 등의 프로필렌글리콜모노알킬에테르류; 디프로필렌글리콜디메틸에테르, 디포로필렌글리콜디에틸에테르 등의 디프로필렌글리콜알킬에테르류; 부틸렌글리콜모노메틸에테르, 부틸렌글리콜모노에틸에테르 등의 부틸렌글리콜모노메틸에테르류; 또는 디부틸렌글리콜디메틸에테르, 디부틸렌글리콜디에틸에테르 등의 디부틸렌글리콜알킬에테르류; 감마부티로락톤 등을 사용할 수 있다.In the present invention, a conventional solvent used for preparing a polyimide photosensitive composition in the art may be used, and specifically, alcohols such as methanol, ethanol, benzyl alcohol and hexyl alcohol; Ethylene glycol alkyl ether acetates such as ethylene glycol methyl ether acetate and ethylene glycol ethyl ether acetate; Ethylene glycol alkyl ether propionates such as ethylene glycol methyl ether propionate and ethylene glycol ethyl ether propionate; Ethylene glycol monoalkyl ethers such as ethylene glycol methyl ether and ethylene glycol ethyl ether; Diethylene glycol alkyl ethers such as diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, and propylene glycol propyl ether acetate; Propylene glycol alkyl ether propionates such as propylene glycol methyl ether propionate, propylene glycol ethyl ether propionate and propylene glycol propyl ether propionate; Propylene glycol monoalkyl ethers such as propylene glycol methyl ether, propylene glycol ethyl ether, propylene glycol propyl ether and propylene glycol butyl ether; Dipropylene glycol alkyl ethers such as dipropylene glycol dimethyl ether and diporoethylene glycol diethyl ether; Butylene glycol monomethyl ether, such as butylene glycol monomethyl ether and butylene glycol monoethyl ether; Or dibutylene glycol alkyl ethers such as dibutylene glycol dimethyl ether and dibutylene glycol diethyl ether; Gamma butyrolactone etc. can be used.
본 발명에 있어서 상기 용매의 함량은 70-90 중량부인 것이 좋으며, 더욱 바람직하기로는 전체 감광성 조성물의 고형분 함량이 15 내지 50 중량%가 되도록 포함되는 것이 바람직하다.
In the present invention, the content of the solvent is preferably 70 to 90 parts by weight, more preferably it is included so that the solid content of the entire photosensitive composition is 15 to 50% by weight.
또한 본 발명의 레이저 열전사용 감광성 조성물은 가교제 및 계면활성제를 추가로 포함할 수 있다. In addition, the laser thermosensitive photosensitive composition of the present invention may further include a crosslinking agent and a surfactant.
바람직하기로 상기 가교제는 멜라닌계 가교제인 것이 좋으며, 본 발명의 감광성 조성물의 1 내지 30 중량부로 포함되는 것이 좋다.Preferably, the crosslinking agent is a melanin-based crosslinking agent, and preferably contained in 1 to 30 parts by weight of the photosensitive composition of the present invention.
또한 상기 계면활성제는 일예로 폴리옥시에틸렌옥틸페닐에테르, 폴리옥시에틸렌노닐페닐에테르, F171, F172, F173(상품명: 대일본잉크사), FC430, FC431(상품명: 수미또모트리엠사), 또는 KP341(상품명: 신월화학공업사) 등을 사용할 수 있으며, 본 발명의 감광성 조성물의 0.0001 내지 2 중량부로 포함되는 것이 바람직하다.
In addition, the surfactant is, for example, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, F171, F172, F173 (trade name: Japan Nippon Ink Company), FC430, FC431 (trade name: Sumitomo Triem, Inc.), or KP341 ( A brand name: Shinwol Chemical Co., Ltd.) etc. can be used, It is preferable that it is contained in 0.0001-2 weight part of the photosensitive composition of this invention.
또한 본 발명은 상기 레이저 열전사용 폴리이미드 감광성 조성물을 이용하여 제조된 절연막 및 이를 포함하는 유기 발광 표시 소자를 제공한다.In another aspect, the present invention provides an insulating film prepared using the polyimide photosensitive composition for laser thermal transfer and an organic light emitting display device including the same.
본 발명의 절연막 형성 방법은 레이저 열전사법을 이용하여 절연막을 제조함에 있어서, 본 발명에 따른 레이저 열전사용 폴리이미드 감광성 조성물을 사용하는 것을 특징으로 하며, 공지의 레이저 열전사법이 적용될 수 있음은 물론이다.
The method for forming an insulating film according to the present invention is characterized by using the laser thermal transfer polyimide photosensitive composition according to the present invention in manufacturing the insulating film using the laser thermal transfer method, and of course, a known laser thermal transfer method may be applied. .
구체적인 일예로 절연막을 형성하는 방법은 다음과 같다.
As a specific example, a method of forming an insulating film is as follows.
통상의 방법에 따라, 본 발명에 따른 감광성 조성물을 코팅한 다음, 프리베이크(Prebake), 노광, 현상 및 경화를 진행하여 절연막을 형성하고, 레이저 전사 공정 진행을 위해 도너(Donor) 필름을 부착하여 레이저 전사를 진행하여 발광층을 형성한 다음(도 1 참조), 도너 필름을 제거한다. 도 1에서 절연막은 전사된 발광층과 기판 사이에 위치한다.
According to a conventional method, the photosensitive composition according to the present invention is coated, followed by prebake, exposure, development and curing to form an insulating film, and attaching a donor film for the laser transfer process. Laser transfer is performed to form a light emitting layer (see FIG. 1), and then the donor film is removed. In FIG. 1, the insulating film is positioned between the transferred light emitting layer and the substrate.
이하, 본 발명의 이해를 돕기 위하여 바람직한 실시예를 제시하나, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명의 범위가 하기 실시예에 한정되는 것은 아니다.
Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the scope of the present invention is not limited to the following examples.
실시예: 폴리이미드 감광성 전구체 및 조성물의 제조EXAMPLES Preparation of Polyimide Photosensitive Precursors and Compositions
하기 표 1에 기재된 함량에 따라 폴리이미드 감광성 전구체 및 조성물을 다음과 같이 제조하였다.
To the polyimide photosensitive precursor and composition according to the content described in Table 1 below was prepared as follows.
실시예 1Example 1
300 ml 4구 반응용기에 DADM 100 g, 6-FDA 80 g, SiDA 5 g 및 감마부티로락톤 70 g을 반응용기에 투입하고 1시간동안 교반하며 반응시켰다. 말단의 반응을 종결하기 위해 PA 2 g을 투입 후 20 ℃에서 1시간동안 추가 반응시켜 고형분 함량 30%의 폴리이미드 전구체를 제조하였다. 여기에 protecting group 물질인 ECMMA 100 g을 투입하고 70 ℃까지 승온 후, 촉매인 트리에틸아민(triethylamine, TEA)를 첨가하고 24 시간 동안 반응시켜 신규 폴리이미드 전구체를 제조하였다.DADM 100 g, 6-FDA 80 g, SiDA 5 g and gamma butyrolactone 70 g in a 300 ml four-necked reaction vessel were added to the reaction vessel and reacted with stirring for 1 hour. In order to terminate the terminal reaction, 2 g of PA was added thereto, and then further reacted at 20 ° C. for 1 hour to prepare a polyimide precursor having a solid content of 30%. 100 g of ECMMA, a protecting group material, was added thereto, and then heated to 70 ° C., triethylamine (TEA) as a catalyst was added thereto, and reacted for 24 hours to prepare a new polyimide precursor.
상기 제조된 폴리이미드 전구체 30 중량부, 하이드록시스티렌 고분자 15 중량부와 PAC 10 중량부를 혼합하였다. 그 다음, 상기 혼합물의 고형분 함량이 20 중량%가 되도록 감마부티로락톤과 프로필렌 글라이콜 모노메틸 에테르 아세트산(propylene glycol monomethyl ether acetate, PGMEA)를 50:50의 중량비로 혼합한 용매로 용해시킨 후, 0.2 ㎛의 밀리포아필터로 여과하여 레이저 열전사용 폴리이미드 감광성 조성물을 제조하였다.
30 parts by weight of the prepared polyimide precursor, 15 parts by weight of hydroxystyrene polymer, and 10 parts by weight of PAC were mixed. Then, the mixture was dissolved in a solvent in which gamma butyrolactone and propylene glycol monomethyl ether acetate (PGMEA) were mixed at a weight ratio of 50:50 so that the solid content of the mixture was 20% by weight. And filtered with a 0.2 μm Millipore filter to prepare a polyimide photosensitive composition for laser thermal transfer.
실시예 2Example 2
상기 실시예 1에서 다이아민계 단량체인 SiDA 대신 아민계 단량체로서 KBM 603을 사용한 것을 제외하고는 상기 실시예 1과 동일한 방법으로 실시하여 레이저 열전사용 폴리이미드 감광성 조성물을 제조하였다.
In Example 1, except that KBM 603 was used as the amine monomer instead of SiDA which is a diamine monomer, it was carried out in the same manner as in Example 1 to prepare a polyimide photosensitive composition for laser thermal transfer.
실시예 3Example 3
상기 실시예 1에서 다이아민계 단량체인 SiDA를 사용하지 않고, protecting group 물질로 ECMMA 100 g 및 GPTS 5 g을 사용한 것을 제외하고는 상기 실시예 1과 동일한 방법으로 실시하여 레이저 열전사용 폴리이미드 감광성 조성물을 제조하였다.
The polyimide photosensitive composition of the laser thermal transfer method was prepared in the same manner as in Example 1, except that 100 g of the ECMMA and 5 g of the GPTS were used as the protecting group material without using SiDA as the diamine monomer in Example 1. Prepared.
비교예 1Comparative Example 1
상기 실시예 1에서 다이아민계 단량체인 SiDA를 사용하지 않은 것을 제외하고는 상기 실시예 1과 동일한 방법으로 실시하여 레이저 열전사용 폴리이미드 감광성 조성물을 제조하였다.A polyimide photosensitive composition was prepared in the same manner as in Example 1, except that SiDA, which is a diamine monomer, was not used in Example 1.
groupprotecting
group
시험예 1: 이중 테이퍼 형성 평가 Test Example 1: Evaluation of Double Taper Formation
ITO 유리 기판 위에 상기 실시예 1 내지 3 및 비교예 1에서 제조한 감광성 수지 조성물을 각각 스핀 코팅하여 두께 0.3 ㎛의 막을 얻었다. 이후, 120℃에서 2 분 동안 프리베이크하고, 20 ㎛의 라인/스페이스를 갖는 포토마스크를 통해 365 ㎚의 파장에서 100 mJ/㎠의 노광에너지를 조사하였다. 그 다음, 2.38% TMAH 현상액에서 35초 동안 현상 후, 230℃의 오븐에서 1 시간 동안 경화시켰다.
Each of the photosensitive resin compositions prepared in Examples 1 to 3 and Comparative Example 1 was spin coated on an ITO glass substrate to obtain a film having a thickness of 0.3 μm. Thereafter, prebaking was performed at 120 ° C. for 2 minutes, and exposure energy of 100 mJ / cm 2 was irradiated at a wavelength of 365 nm through a photomask having a line / space of 20 μm. Then, after developing for 35 seconds in a 2.38% TMAH developer, it was cured for 1 hour in an oven at 230 ℃.
이중 테이퍼가 형성되었는지를 확인하기 위하여, 형성된 패턴의 단면을 SEM 으로 관찰하였다. 이때, 메인 테이퍼(두께 0.3 ㎛) 아래에 형성된 이중 테이퍼의 두께가 0.1 ㎛ 이하, 이중 테이퍼의 길이가 0.3 ㎛ 내지 1 ㎛ 범위로 관찰되면 이중테이퍼가 형성된 것으로 판단하였다. 그 결과를 하기 표 2에 나타내었다.
In order to confirm whether double taper was formed, the cross section of the formed pattern was observed by SEM. At this time, when the thickness of the double taper formed below the main taper (thickness 0.3 μm) was 0.1 μm or less and the length of the double taper was observed in the range of 0.3 μm to 1 μm, it was determined that the double taper was formed. The results are shown in Table 2 below.
상기 표 2에 나타낸 바와 같이, 본 발명에 따른 폴리이미드 감광성 조성물을 사용하여 절연막을 형성하면, 이중 테이퍼 패턴을 형성할 수 있음을 알 수 있지만, 비교예 1의 경우에는 이중 테이퍼 패턴이 형성되지 않았다.As shown in Table 2, it can be seen that when the insulating film is formed using the polyimide photosensitive composition according to the present invention, a double tapered pattern can be formed, but in the case of Comparative Example 1, a double tapered pattern was not formed. .
Claims (13)
(1) 폴리이미드 전구체 20 내지 40 중량부;
(2) 하이드록시스티렌 고분자 10 내지 20 중량부;
(3) PAC 3 내지 20 중량부; 및
(4) 용매 70 내지 90 중량부를 포함하는 것을 특징으로 하는 레이저 열전사용 폴리이미드 감광성 조성물.The method of claim 1,
(1) 20 to 40 parts by weight of the polyimide precursor;
(2) 10 to 20 parts by weight of hydroxystyrene polymer;
(3) 3 to 20 parts by weight of PAC; And
(4) A laser thermal transfer polyimide photosensitive composition comprising 70 to 90 parts by weight of a solvent.
상기 폴리이미드 전구체가 하기 화학식 1로 표시되는 것을 특징으로 하는 레이저 열전사용 폴리이미드 감광성 조성물;
[화학식 1]
상기 화학식 1에서,
X는 4가의 유기기이고;
Y는 일부 또는 전체가 1,3-비스(3-아미노프로필)테트라메틸다이실록산(SiDA) 또는 N-2(아미노에틸)3-아미노프로필트라이메톡시실란(KBM-603)인 유기기이고;
R은 각각 독립적으로 에폭시 사이클로헥실 메틸 메타크릴레이트(ECMMA) 또는 (3-글리시딜옥시프로필)트라메톡시실란(GPTS)이며;
n은 3 내지 100,000의 정수이다.The method of claim 1,
A polyimide photosensitive composition for laser thermal transfer, wherein the polyimide precursor is represented by the following Chemical Formula 1;
[Formula 1]
In Chemical Formula 1,
X is a tetravalent organic group;
Y is an organic group in which part or all is 1,3-bis (3-aminopropyl) tetramethyldisiloxane (SiDA) or N-2 (aminoethyl) 3-aminopropyltrimethoxysilane (KBM-603);
Each R is independently epoxy cyclohexyl methyl methacrylate (ECMMA) or (3-glycidyloxypropyl) tramethoxysilane (GPTS);
n is an integer from 3 to 100,000.
상기 화학식 1의 X가 2,2-비스(3,4-안하이드로다이카복시페닐)헥사플루오로프로판(6FDA), 5-(2,5-다이옥소테트라하이드로퓨릴)-3-메틸-3-사이클로헥센-1,2-다이카복실산 무수물(DOCDA), 또는 2,3,3',4'-바이페닐 테트라카복실산 이무수물(a-BPDA)으로부터 유도된 4가의 유기기인 것을 특징으로 하는 레이저 열전사용 폴리이미드 감광성 조성물.The method of claim 3,
X in Chemical Formula 1 is 2,2-bis (3,4-anhydrodicarboxyphenyl) hexafluoropropane (6FDA), 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3- Laser thermal transfer characterized in that it is a tetravalent organic group derived from cyclohexene-1,2-dicarboxylic acid anhydride (DOCDA) or 2,3,3 ', 4'-biphenyl tetracarboxylic dianhydride (a-BPDA) Polyimide photosensitive composition.
상기 화학식 1의 Y 중 일부가 4,4'-다이아미노-3,3'-다이메틸-다이페닐메탄(DADM) 또는 2,2-비스(3-아미노-4-하이드록시페닐)-헥사플루오로프로판(Bis-APAF)으로부터 유도된 2가의 유기기인 것을 특징으로 하는 레이저 열전사용 폴리이미드 감광성 조성물.The method of claim 3,
Some of Y in Formula 1 is 4,4'-diamino-3,3'-dimethyl-diphenylmethane (DADM) or 2,2-bis (3-amino-4-hydroxyphenyl) -hexafluoro A polyimide photosensitive composition for laser thermal transfer, characterized in that it is a divalent organic group derived from biropan (Bis-APAF).
상기 Y 중 3-50 몰%가 1,3-비스(3-아미노프로필)테트라메틸다이실록산(SiDA) 또는 N-2(아미노에틸)3-아미노프로필트라이메톡시실란(KBM-603)로 유도된 유기기인 것을 특징으로 하는 레이저 열전사용 폴리이미드 감광성 조성물.The method of claim 3,
3-50 mole% of the Y is derived from 1,3-bis (3-aminopropyl) tetramethyldisiloxane (SiDA) or N-2 (aminoethyl) 3-aminopropyltrimethoxysilane (KBM-603) A polyimide photosensitive composition for laser thermal transfer, comprising: an organic group.
상기 R이 에폭시 사이클로헥실 메틸 메타크릴레이트(ECMMA):(3-글리시딜옥시프로필)트라메톡시실란(GPTS)의 비율이 몰비로 80-99:1-20인 것을 특징으로 하는 레이저 열전사용 폴리이미드 감광성 조성물.The method of claim 3,
Wherein R is the ratio of epoxy cyclohexyl methyl methacrylate (ECMMA) :( 3-glycidyloxypropyl) tramethoxysilane (GPTS) in a molar ratio of 80-99: 1-20 Polyimide photosensitive composition.
상기 하이드록시스티렌 고분자가 폴리스티렌 환산중량평균분자량(Mw)이 4,000-20,000인 것을 특징으로 하는 레이저 열전사용 폴리이미드 감광성 조성물.The method of claim 1,
The hydroxystyrene polymer polystyrene reduced weight average molecular weight (Mw) is characterized in that the polyimide photosensitive composition for laser thermal transfer, characterized in that 4,000-20,000.
상기 용매가 알코올류; 에틸렌글리콜알킬에테르아세테이트류; 에틸렌글리콜알킬에테르프로피오네이트류; 에틸렌글리콜모노알킬에테르류; 디에틸렌글리콜알킬에테르류; 프로필렌글리콜알킬에테르아세테이트류; 프로필렌글리콜알킬에테르프로피오네이트류; 프로필렌글리콜모노알킬에테르류; 디프로필렌글리콜알킬에테르류; 부틸렌글리콜모노메틸에테르류; 및 디부틸렌글리콜알킬에테르류; 감마부티로락톤으로 이루어진 군으로부터 선택된 1종 이상의 것임을 특징으로 하는 레이저 열전사용 폴리이미드 감광성 조성물.The method of claim 1,
The solvent is an alcohol; Ethylene glycol alkyl ether acetates; Ethylene glycol alkyl ether propionates; Ethylene glycol monoalkyl ethers; Diethylene glycol alkyl ethers; Propylene glycol alkyl ether acetates; Propylene glycol alkyl ether propionates; Propylene glycol monoalkyl ethers; Dipropylene glycol alkyl ethers; Butylene glycol monomethyl ethers; And dibutylene glycol alkyl ethers; A polyimide photosensitive composition for laser thermal transfer, characterized in that at least one member selected from the group consisting of gamma butyrolactone.
가교제 및 계면활성제를 추가로 포함하는 것을 특징으로 하는 레이저 열전사용 폴리이미드 감광성 조성물.The method of claim 1,
A laser thermal transfer polyimide photosensitive composition, further comprising a crosslinking agent and a surfactant.
상기 절연막은 이중 테이퍼 패턴을 갖는 것을 특징으로 하는 OLED 절연막.The method of claim 11,
And the insulating film has a double tapered pattern.
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| PCT/KR2012/010213 WO2013085223A1 (en) | 2011-12-06 | 2012-11-29 | Polyimide photosensitive composition for laser-induced thermal imaging |
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