TWI397772B - Photoresist composition for colour filter and preparation method of liquid crystal display colour filter using the same - Google Patents
Photoresist composition for colour filter and preparation method of liquid crystal display colour filter using the same Download PDFInfo
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- TWI397772B TWI397772B TW094141689A TW94141689A TWI397772B TW I397772 B TWI397772 B TW I397772B TW 094141689 A TW094141689 A TW 094141689A TW 94141689 A TW94141689 A TW 94141689A TW I397772 B TWI397772 B TW I397772B
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D1/00—Processes for applying liquids or other fluent materials
- B05D1/002—Processes for applying liquids or other fluent materials the substrate being rotated
- B05D1/005—Spin coating
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
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Description
本發明係關於一種彩色濾光片用感光性樹脂組成物及利用該組成物之液晶顯示器彩色濾光片的製造方法，尤其是在TFT及STN方式的LCD製造程序中，可以使發生在被旋轉塗布於基板上的光阻膜之周緣部分(Edge part)的不必要部分(Edge Bead：Edge B)最少化，並使塗布性和平準化提高之彩色濾光片用感光性樹脂組成物，以及利用該組成物之穿透型、反射型或半穿透型(half－transparent type)液晶顯示器彩色濾光片的製造方法。The present invention relates to a photosensitive resin composition for a color filter and a method for producing a color filter of a liquid crystal display using the composition, particularly in a TFT and STN type LCD manufacturing process, which can be caused to be rotated a photosensitive resin composition for a color filter which minimizes an unnecessary portion (Edge Bead: Edge B) of a peripheral portion of a photoresist film coated on a substrate, and which improves applicability and leveling, and A method of producing a pass-through, reflective or half-transparent type liquid crystal display color filter of the composition.
關於液晶顯示器之彩色濾光片的形成方法過去雖可使用印刷方式，電極沈積方式、噴墨(Ink－jet)方式、顏料分散方式等，最近則是採用圖案的精巧性(Resolution)及製造方法容易的顏料分散方式；此種方式已應用於製造行動電話、筆記型電腦、監視器、TV等之LCD上。In the past, a method of forming a color filter for a liquid crystal display may use a printing method, an electrode deposition method, an inkjet method, a pigment dispersion method, etc., and recently, a pattern resolution and a manufacturing method are employed. Easy pigment dispersion method; this method has been applied to LCDs for mobile phones, notebook computers, monitors, TVs, etc.
最近對於具有多種優點的顏料分散型著色組成物，不僅要求圖案的精巧性，更進一步要求提昇性能。也就是說，一般的顏料分散型著色組成物係透過塗布於基板曝光後顯像的作用而形成著色畫素，此時利用在受到曝光的畫素造成適當的硬化而即使在顯像液中也不會被溶解。Recently, for pigment-dispersed coloring compositions having various advantages, not only the delicateness of the pattern is required, but also the performance is required to be improved. In other words, a general pigment dispersion type coloring composition forms a color pixel by being applied to a substrate after exposure to light, and at this time, it is appropriately hardened by the exposed pixel, even in a developing liquid. Will not be dissolved.
此種TFT－LCD工程係在玻璃基板上塗布彩色光阻(R、G、B)，依序進行曝光及顯像步驟，通常會發生因為經過塗布的基板在移動時造成裝備污染、曝光步驟時難以確實地對準，在顯像步驟後又因為膜的厚度厚而無法完全顯像的情形而產生之EB部分殘存下來的問題；為解決這個問題，必須進行EBR(Edge Bead Remover)步驟將發生在被旋轉塗布於基板上之光阻膜的周緣部分之EB部分用稀釋劑除去。Such a TFT-LCD project is to apply a color photoresist (R, G, B) on a glass substrate, and sequentially perform exposure and development steps, which usually occurs because the coated substrate causes equipment contamination when moving, and an exposure step. It is difficult to align correctly, and the problem of EB part remaining after the development step is caused by the thickness of the film being too thick to be fully imaged; in order to solve this problem, an EBR (Edge Bead Remover) step must occur. The EB portion of the peripheral portion of the photoresist film spin-coated on the substrate is removed with a diluent.
但是，最近在STN方式和TFT－LCD程序中因為步驟數的簡約化，而以選擇省略EBR步驟的方式為佳。若省略前述EBR處理步驟，則因為在彩色濾光片的製造程序中至少可以不用進行3~4次的EBR處理步驟，不僅可以使全體製造程序單純化並節約製造時間，而且可以因為不使用EBR處理步驟中所使用的稀釋劑組成物，故而具有節省費用以及可以形成接近於對環境友善的製造程序之優點。However, recently, in the STN method and the TFT-LCD program, it is preferable to select the method of omitting the EBR step because of the simplification of the number of steps. If the EBR processing step is omitted, since it is not necessary to perform at least 3 to 4 EBR processing steps in the color filter manufacturing process, not only the entire manufacturing process can be simplistic and manufacturing time can be saved, but also EBR can be used. The diluent composition used in the processing step has the advantage of being cost effective and capable of forming a manufacturing process that is close to environmentally friendly.
為了省略此種EBR處理步驟，要透過使旋轉塗布時發生在光阻膜的周緣部分之不必要的膜部分更進一步地最少化(寬度、厚度)的作法，特別是即使不進行EBR步驟依然可以在一般的顯像步驟時間內防止不必要的膜之發生。另外，因為基板的尺寸有越來越大的傾向，故而要求彩色光阻塗布時所塗布的膜段差要最少化而且塗布性要提高，基於這些原因，彩色光阻組成物之改善作業乃有其需求。In order to omit such an EBR treatment step, it is necessary to further minimize the (width, thickness) of the unnecessary film portion which occurs in the peripheral portion of the photoresist film during spin coating, in particular, even if the EBR step is not performed. Prevent unnecessary filming during normal imaging steps. In addition, since the size of the substrate tends to be larger and larger, it is required to minimize the difference in film thickness applied during color resist coating and to improve the coating property. For these reasons, the improvement of the color photoresist composition is demand.
然而，過去所使用的感光性樹脂組成物因為EB的寬度及厚度相當大，故有如果不實施EBR步驟就不可能用一般的顯像步驟完美地除去EB部分的問題。However, since the photosensitive resin composition used in the past has a relatively large width and thickness of EB, there is a problem that it is impossible to remove the EB portion perfectly by a general developing step without performing the EBR step.
本發明之目的即是為了解決此種習知的問題，而提供一種使流變特性(property of fluid strain)改善、變化而讓發生在旋轉塗布於基板上的光阻膜的周緣部分之不必要的EB部分最少化，並且使塗布性及平準化提昇之彩色濾光片用感光性樹脂組成物。SUMMARY OF THE INVENTION An object of the present invention is to solve such a conventional problem and to provide an improvement in a property of a fluid strain, which is unnecessary for a peripheral portion of a photoresist film which is applied to a substrate by spin coating. The EB portion is minimized, and a photosensitive resin composition for a color filter having improved coatability and leveling is used.
另外，本發明之目的在於提供一種可以使發生在旋轉塗布於基板上的光阻膜的周緣部分之不必要的EB部分最少化，而於液晶顯示器彩色濾光片的製造時可以省略EBR步驟，從而可以突破性地減少製造成本之液晶顯示器彩色濾光片的製造方法。Further, it is an object of the present invention to provide an EB portion which is unnecessary for the peripheral portion of the photoresist film which is applied to the substrate by spin coating, and the EBR step can be omitted in the manufacture of the color filter of the liquid crystal display. Therefore, it is possible to drastically reduce the manufacturing cost of the liquid crystal display color filter.
為達成前述目的，本發明提供一種彩色濾光片用感光性樹脂組成物，其特徵在於其中含有從聚乙烯氧甲矽烷(polyaokylene oxide methylsilane)高分子、聚醚變形而成之聚二甲基矽氧烷(dimethyl polysiloxane)高分子溶液及聚醚變形而成之聚二甲基矽氧烷高分子所組成的族群中選擇出之1種以上的矽系表面添加劑。In order to achieve the above object, the present invention provides a photosensitive resin composition for a color filter comprising a polydimethyl hydrazine obtained by deforming a polyaokylene oxide methylsilane polymer or a polyether. One or more kinds of lanthanide surface additives selected from the group consisting of a dimethyl polysiloxane polymer solution and a polydimethyl methoxy siloxane polymer obtained by deforming a polyether.
另外，本發明提供一種液晶顯示器彩色濾光片的製造方法，特徵在於其中包含將前述彩色濾光片用感光性樹脂組成物塗布於基板的步驟。Moreover, the present invention provides a method of producing a color filter for a liquid crystal display, which comprises the step of applying a photosensitive resin composition for a color filter to a substrate.
本發明之彩色濾光片用感光性樹脂組成物係使流變特性改善、變化而可以使在旋轉塗布於基板上的光阻膜之周緣部分所發生的不必要EB部分最少化，並且使塗布性及平準化提昇；利用前述彩色濾光片用感光性樹脂組成物之液晶顯示器彩色濾光片的製造方法則可以提高塗布性，使發生在經旋轉塗布之光阻膜的周緣部分之不必要的EB部分最少化，而可以在製造液晶顯示器彩色濾光片時省略EBR步驟，並藉之而可以將製造價格突破性地減低。The photosensitive resin composition for a color filter of the present invention can improve the rheological properties and change, and can minimize unnecessary EB portions occurring at the peripheral portion of the photoresist film spin-coated on the substrate, and can be coated. Improvement of the properties and leveling; the method for producing a liquid crystal display color filter using the photosensitive resin composition for a color filter described above can improve the coating property and make it unnecessary for the peripheral portion of the spin-coated photoresist film to occur. The EB portion is minimized, and the EBR step can be omitted in the manufacture of a liquid crystal display color filter, and the manufacturing price can be drastically reduced.
以下將就本發明做詳細說明。The invention will be described in detail below.
本發明之彩色濾光片用感光性樹脂組成物之特徵在於添加了從聚乙烯氧甲矽烷高分子、聚醚變形而成之聚二甲基矽氧烷高分子溶液及聚醚變形而成之聚二甲基矽氧烷高分子所組成的族群中選擇1種以上之矽系表面添加劑。前述矽系表面添加劑於旋轉塗布於基板時會導致表面張力減少，而有在基板上之濕潤性良好和防止沾污現象等的效果。前述矽系表面添加劑的含量相對於全體組成物以使用0.1~2重量%為佳。前述添加劑的含量如果未達0.1重量%，塗布時就不能順利地在基板全體實行均勻的塗布，而如果超過2重量%，則塗布時發生沾污的頻率會增高。較佳為前述高分子的分子量為1,000~100,000，更佳為3,000~10,000。另外，前述矽系表面添加劑的溶劑以使用無溶劑形態之苯氧乙醇(phenoxy ethanol)/二甲苯(xylene)為佳。The photosensitive resin composition for a color filter of the present invention is characterized in that a polydimethylsiloxane polymer solution obtained by deforming a polyoxymethylene polymer or a polyether and a polyether are modified. One or more kinds of lanthanide surface additives are selected from the group consisting of polydimethyl siloxane polymers. When the above-mentioned lanthanide surface additive is spin-coated on a substrate, surface tension is reduced, and there is an effect of good wettability on the substrate and prevention of contamination. The content of the above-mentioned lanthanoid surface additive is preferably 0.1 to 2% by weight based on the total composition. When the content of the above-mentioned additive is less than 0.1% by weight, uniform coating on the entire substrate cannot be smoothly performed at the time of coating, and if it exceeds 2% by weight, the frequency of occurrence of contamination at the time of coating increases. It is preferred that the polymer has a molecular weight of 1,000 to 100,000, more preferably 3,000 to 10,000. Further, the solvent of the above-mentioned lanthanoid surface additive is preferably phenoxy ethanol/xylene in a solventless form.
若舉本發明之彩色濾光器用感光性樹脂組成物的較佳一例，則包含A)鹼可溶性接著劑、B)至少具有2個以上之乙烯系雙鍵的交聯性單體、C)顏料、D)光聚合起始劑、E)前述矽系表面添加劑，以及F)溶劑。A preferred example of the photosensitive resin composition for a color filter of the present invention comprises A) an alkali-soluble binder, B) a crosslinkable monomer having at least two or more vinyl double bonds, and C) a pigment. And D) a photopolymerization initiator, E) the aforementioned lanthanide surface additive, and F) a solvent.
本發明之彩色濾光片用感光性樹脂組成物中，前述A)鹼可溶性接著劑以高分子鏈中是具有乙烯系酸性基的單體和不具有乙烯系酸性基的單體之共聚物者為佳。In the photosensitive resin composition for a color filter of the present invention, the A) alkali-soluble adhesive agent is a copolymer of a monomer having a vinyl acid group and a monomer having no vinyl acid group in the polymer chain. It is better.
前述具有乙烯系酸性基的單體有丙烯酸、甲基丙烯酸、衣康酸(itaconic acid)、馬來酸、富馬酸、乙烯基乙酸(vinylacetic acid)或其等之酸酐形態，或者鄰苯二甲酸氫－2－丙烯氧乙基酯(2－acrylooxyethylhydrogenphthalate)、鄰苯二甲酸氫－2－丙烯氧丙基酯(2－acrylooxypropylhydrogen－phthalate)、鄰苯二甲酸六氫－2－丙烯氧丙基酯(2－acrylo－oxypropylhexahydrogenphthalate)等，其等可以單獨使用1種或混合2種以上來使用。前述具有乙烯系酸性基之單體的含量以占前述鹼可溶性接合劑之10~40重量%為佳，較佳為15~35重量%。如果前述具有酸性基的單體之含量未達10重量%，則對感光性樹脂組成物的鹼性顯像液之溶解性有降低的傾向；如果超過40重量%，則利用鹼性顯像液進行顯像時會發生圖案的脫落及剝離現象。The monomer having a vinylic acid group is an acid anhydride form of acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, vinylacetic acid or the like, or phthalic acid. 2-acrylooxyethylhydrogenphthalate, 2-acrylooxypropylhydrogen-phthalate, hexahydro-2-propoxypropyl phthalate (2-acrylo-oxypropylhexahydrogenphthalate), etc., may be used alone or in combination of two or more. The content of the monomer having a vinyl acid group is preferably from 10 to 40% by weight, preferably from 15 to 35% by weight, based on the alkali-soluble binder. When the content of the monomer having an acidic group is less than 10% by weight, the solubility of the alkaline developing solution of the photosensitive resin composition tends to be lowered; if it exceeds 40% by weight, the alkaline developing solution is used. Pattern peeling and peeling occur during development.
另外，前述不具有酸性基的單體之例有，丙烯酸異丁酯、丙烯酸特丁酯(t－butyl acrylate)、丙烯酸十二烷基酯(lauryl acrylate)、丙烯酸烷基酯(alkyl acrylate)、丙烯酸十八烷基酯(stearic acrylate)、丙烯酸環己基酯、丙烯酸異冰片酯(isobornyl acrylate)、丙烯酸苄酯(benzyl acrylate)、丙烯酸－2－羥基酯(2－hydroxy acrylate)、丙烯酸三甲氧基丁酯(trimethoxybutyl acrylate)、乙基卡必醇丙烯酸酯(ethyl－carbitolacrylate)、丙烯酸苯氧基乙酯(phenoxyethyl acrylatE)、丙烯酸－4－羥基丁酯(4－hydroxybutyl acrylate)、苯氧基聚乙二醇丙烯酸酯(phenoxypolyethylene glycol acrylate)、丙烯酸－2－羥基乙酯(2－hydroxyethyl acrylate)、丙烯酸羥乙基肉桂酯(hydroxyethylcinnamic acrylate)、丙烯酸－2－羥基丙酯(2－hydroxypropyl acrylate)、鄰苯二甲酸－2－丙烯氧基乙基－2－羥基丙酯(2－acryloxyethyl－2－hydroxypropyl phthalate)、丙烯酸－2－羥基－3－苯氧基丙酯(2－hydroxy－3－phenoxypropyl acrylate)及其等之甲基丙烯酯類；丙烯酸－3－氟乙酯(3－fluoro－ethyl acrylate)、丙烯酸－4－氟丙酯(4－fluoropropyl acrylate)之類的含有鹵化合物之丙烯酸酯及其等之甲基丙烯酸酯類；丙烯酸三乙基矽氧烷乙酯(triethylsiloxylethyl acrylate)之類的含有矽氧烷基之丙烯酸酯及其等之甲基丙烯酸酯類；苯乙烯、4－甲氧基苯乙烯之類的具有芳香族的烯烴類等；這些化合物可以單獨或混合2種以上來使用。Further, examples of the monomer having no acidic group include isobutyl acrylate, t-butyl acrylate, lauryl acrylate, and alkyl acrylate. Stearic acrylate, cyclohexyl acrylate, isobornyl acrylate, benzyl acrylate, 2-hydroxy acrylate, trimethoxy acrylate Trimethoxybutyl acrylate, ethyl-carbitolacrylate, phenoxyethyl acrylatE, 4-hydroxybutyl acrylate, phenoxy polyethyl acrylate Phenoxypolyethylene glycol acrylate, 2-hydroxyethyl acrylate, hydroxyethylcinnamic acrylate, 2-hydroxypropyl acrylate, neighbor 2-acryloxyethyl-2-hydroxypropyl phthalate, 2-hydroxy acrylate 3-hydroxy-3-phenoxypropyl acrylate and its etc. methacrylates; 3-fluoro-ethyl acrylate, 4-fluoropropyl acrylate a acrylate containing a halogen compound such as (4-fluoropropyl acrylate) and a methacrylate thereof, and a decyloxy group-containing acrylate such as triethylsiloxylethyl acrylate A methacrylate such as styrene or an aromatic olefin such as styrene or 4-methoxystyrene; and these compounds may be used alone or in combination of two or more.
前述不具有酸性基的單體之含量以占前述鹼可溶性接著劑的60~90重量%為佳，更佳為65~85重量%。如果前述不具有酸性基的單體之含量未達60重量%，則於顯像步驟時與基板的密著性會降低，圖案剝離現象變劇烈，所形成的圖案平直性惡化；如果超過90重量%，顯像時對鹼性顯像液的溶解速度減少，顯像時間變長。The content of the monomer having no acidic group is preferably from 60 to 90% by weight, more preferably from 65 to 85% by weight, based on the alkali-soluble binder. If the content of the monomer having no acidic group is less than 60% by weight, the adhesion to the substrate during the developing step is lowered, the pattern peeling phenomenon is severe, and the flatness of the formed pattern is deteriorated; if it exceeds 90 The weight % shows a decrease in the dissolution rate of the alkaline developing solution at the time of development, and the development time becomes long.
另外，本發明之感光性樹脂組成物中，B)至少具有2個以上之乙烯系雙鍵的交聯性單體可舉例如，1,4－丁二醇二丙烯酸酯(1,4－dibutadiol diacrylate)、1,3－丁二醇二丙烯酸酯(1,3－butyleneglycol diacrylate)、乙二醇二丙烯酸酯(ethylene glycol diacylate)、異戊四醇四丙烯酸酯(pentaerythritol tetra－acylate)、三甘醇二丙烯酸酯(triethyleneglycol diacrylate)、聚乙二醇二丙烯酸酯(polyethyleneglycol diacrylate)、山梨醇三丙烯酸酯(sorbitol triacrylate)、雙酚A二丙烯酸酯(bisphenol A diacrylate)衍生物、三甲基丙烷三丙烯酸酯(trimethylpropane triacrylate)、二異戊四醇二丙烯酸酯(di－pentaerythritol diacylate)、二異戊四醇六丙烯酸酯(dipenta－erythritol hexaacylate)及其等之甲基丙烯酸酯類等。前述至少具有2個以上之乙烯系雙鍵的交聯性單體之含量以相對於全體感光性樹脂組成物占5~30重量%為佳，更佳為5~20重量%。如果前述交聯性單體的含量未達5重量%，則因和感光性樹脂的低硬化度會造成難以實現圖案；而如果超過30重量%，則不僅光阻組成物的粘度(viscosity)會過度上昇，對鹼性顯像液的溶解速度也變得太快，在曝光部對顯像液的抵抗性也顯著降低。Further, in the photosensitive resin composition of the present invention, B) a crosslinkable monomer having at least two or more ethylene double bonds, for example, 1,4-butanediol diacrylate (1,4-dibutadiol) Diacrylate), 1,3-butyleneglycol diacrylate, ethylene glycol diacylate, pentaerythritol tetra-acylate, tripartite Triethyleneglycol diacrylate, polyethyleneglycol diacrylate, sorbitol triacrylate, bisphenol A diacrylate derivative, trimethylpropane Trimethylpropane triacrylate, di-pentaerythritol diacylate, dipenta-erythritol hexaacylate and the like methacrylates. The content of the crosslinkable monomer having at least two or more ethylene double bonds is preferably from 5 to 30% by weight, more preferably from 5 to 20% by weight, based on the entire photosensitive resin composition. If the content of the crosslinkable monomer is less than 5% by weight, it is difficult to achieve a pattern due to a low degree of hardening with the photosensitive resin; and if it exceeds 30% by weight, not only the viscosity of the photoresist composition will be Excessively rising, the dissolution rate of the alkaline developing solution is also too fast, and the resistance to the developing solution at the exposed portion is also remarkably lowered.
再者，本發明之感光性樹脂組成物中，C)顏料可以全部使用有機顏料或無機顏料，此種有機顏料的具體例有，C.I.pigment yellow 83、C.I.pigment yellow 150、C.I.pigment yellow 138、C.I.pigment yellow 128、C.I.pigment orange 43、C.I.pigment red 177、C.I.pigment red 202、C.I.pigment red 209、C.I.pigment red 254、C.I.pigment red 255、C.I.pigment green 7、C.I.pigment green 36、C.I.pigment blue 15、C.I.pigment blue 15：6、C.I.pigment violet 23、C.I.pigment black 1、C.I.pigment black 7等。而，無機顏料可舉例如氧化鈦、鈦黑(titanium black)、碳黑(carbon black)等。為了調合色彩可以將這些顏料混合1種或2種以上來使用。前述顏料的含量以相對於全體感光性樹脂組成物占10~60重量%為佳。Further, in the photosensitive resin composition of the present invention, all of the C) pigments may be organic pigments or inorganic pigments, and specific examples of such organic pigments include CIpigment yellow 83, CIpigment yellow 150, CIpigment yellow 138, CI. Pigment yellow 128, CIpigment orange 43, CIpigment red 177, CIpigment red 202, CIpigment red 209, CIpigment red 254, CIpigment red 255, CIpigment green 7, CIpigment green 36, CIpigment blue 15, CI Pigment blue 15:6, CIpigment violet 23, CIpigment black 1, CIpigment black 7, etc. Further, examples of the inorganic pigment include titanium oxide, titanium black, carbon black, and the like. These pigments may be used in combination of one or two or more kinds in order to blend colors. The content of the pigment is preferably from 10 to 60% by weight based on the total photosensitive resin composition.
此外，本發明之感光性樹脂組成物中，D)光聚合起始劑為可以利用可見光線、紫外線、遠紅外線等的波長而使前述交聯性單體開始聚合的化合物。前述光聚合起始劑可以從三嗪(triazine)系化合物、乙醯苯(acetophenone)系化合物、呫噸酮(xanthone)系化合物、安息香(benzoin)系化合物及咪唑(imidazole)系化合物所組成的族群選擇1種以上來使用。Further, in the photosensitive resin composition of the present invention, D) the photopolymerization initiator is a compound which can start polymerization of the crosslinkable monomer by using a wavelength such as visible light, ultraviolet light or far infrared ray. The photopolymerization initiator may be composed of a triazine compound, an acetophenone compound, a xanthone compound, a benzoin compound, and an imidazole compound. One or more types of ethnic groups are used.
前述三嗪系化合物之具體例有，2,4－雙三氯甲基－6－p－甲氧基苯乙烯基－s－三嗪(2,4－bistrichloromethyl－6－p－methoxy－styryl－s－triazine)、2－p－甲氧基苯乙烯基－4,6－雙三氯甲基－s－三嗪(2－p－methoxystyryl－4,6－bistrichloromethyl－s－triazine)、2,4－三氯甲基－6－三嗪(2,4－trichloromethyl－6－triazine)、2－(2－溴－4－甲基苯)－4,6－雙(三氯甲基)－s－三嗪(2－(2－bromo－4－methylphenyl)－4,6－bis(trichloromethyl)－s－triazine)等。但是，使用前述三嗪系起始劑時，因為對光的反應速度快，所以感度佳，但是曝光時會產生鹵化合物的氣體，有使光罩等之機器受到污染的情形，因為有大體上是固有的黃色之故，所以會使亮度降低。因此，前述三嗪系起始劑的含量以未達全體感光性樹脂組成物的1重量%為佳。A specific example of the above triazine-based compound is 2,4-bistrichloromethyl-6-p-methoxystyryl-s-triazine (2,4-bistrichloromethyl-6-p-methoxy-styryl- S-triazine), 2-p-methoxystyryl-4,6-bistrichloromethyl-s-triazine, 2, 4-trichloromethyl-6-triazine, 2-(2-bromo-4-methylphenyl)-4,6-bis(trichloromethyl)-s - 2-(2-bromo-4-methylphenyl)-4,6-bis(trichloromethyl)-s-triazine). However, when the triazine-based initiator is used, since the reaction rate with respect to light is fast, the sensitivity is good, but a gas of a halogen compound is generated during exposure, and a device such as a photomask is contaminated because there is a general It is inherently yellow, so it will reduce the brightness. Therefore, the content of the above triazine-based initiator is preferably less than 1% by weight of the entire photosensitive resin composition.
而，前述乙醯苯系化合物之具體例有，二苯甲酮(benzo－phenone)、p－(二甲氨基)二苯甲酮(p－(dimethylamino)benzo－phenone)、2,2－二氯－4－苯氧基乙醯苯(2,2－dichloro－4－phenoxy acetophenone)、4,4－雙二乙氨基二苯甲酮(4,4－bisdiethyl－amino benzophenoe)、2,2－二乙氧基乙醯苯(2,2－diethoxy－acetophenone)、2,2－二丁氧基乙醯苯(2,2－dibutoxyaceto－phenone)、2－羥－2－甲基苯丙酮(2－hydroxy－2－methylpropion phenone)、p－t－丁基三氯乙醯苯(p－t－butyltrichloroaceto－phenone)等。而，前述呫噸酮系化合物的具體例有呫噸酮(xanthone)、噻噸酮(thioxanthone)、2－甲基噻噸酮(2－methyl－thioxanthone)、2－異丁基噻噸酮(2－isobutylthioxanthone)、2－十二烷基噻噸酮(2－dodecylthioxanthone)、2,4－二甲基噻噸酮(2,4－dimethylthioxanthone)等。另外，前述安息香系化合物之具體例有，安息香、安息香***(benzoin ethyl ether)、安息香甲醚(bezoin methyl ether)、苯甲醯丙醚(benzoyl propyl ether)、t－丁基苯甲醯醚(t－butyl benzoyl ether)等之類的化合物。此外，咪唑系化合物之具體例有，2,2－雙－2－氯苯基－4,5,4,5－四苯基－2－1,2－聯咪唑(2,2－bis－2－chlorophenyl－4,5,4,5－tetraphenyl－2－1,2－biimidazole)、2,2－雙(2,4,6－三氰基苯基)－4,4,5,5－四苯基－1,2－聯咪唑(2,2－bis－2－(2,4,6－tricyano－phenyl)－4,4,5,5－tetraphenyl－1,2－biimidazole)等之化合物。Specific examples of the acetaminophen compound include benzo-phenone, p-(dimethylamino)benzo-phenone, and 2,2-di. 2,2-dichloro-4-phenoxy acetophenone, 4,4-bisdiethyl-amino benzophenoe, 2,2- 2,2-diethoxy-acetophenone, 2,2-dibutoxyaceto-phenone, 2-hydroxy-2-methylpropiophenone (2 -hydroxy-2-methylpropion phenone), p-t-butyltrichloroacetophenone (p-t-butyltrichloroaceto-phenone). Further, specific examples of the aforementioned xanthone-based compound are xanthone, thioxanthone, 2-methyl-thioxanthone, 2-isobutylthioxanthone ( 2-isobutylthioxanthone), 2-dodecylthioxanthone, 2,4-dimethylthioxanthone, and the like. Further, specific examples of the aforementioned benzoin-based compound include benzoin ethyl ether, bezoin methyl ether, benzoyl propyl ether, and t-butyl benzamidine ( A compound such as t-butyl benzoyl ether) or the like. Further, specific examples of the imidazole-based compound are 2,2-bis-2-chlorophenyl-4,5,4,5-tetraphenyl-2-1,2-biimidazole (2,2-bis-2) -chlorophenyl-4,5,4,5-tetraphenyl-2-1,2-biimidazole), 2,2-bis(2,4,6-tricyanophenyl)-4,4,5,5-tetra A compound such as phenyl-1,2-bis-2-(2,4,6-tricyano-phenyl-4,4,5,5-tetraphenyl-1,2-biimidazole).
前述光聚合起始劑可依需要而和增感劑(例如，光增感劑)、硬化促進劑等混合使用，其具體例有，4－二甲基胺基苯甲酮(4－dimethylamino bezophenone)、異丙基噻噸酮(isobutyl thioxanthone)、甲基－o－苯甲醯基苯甲酸酯(methyl－o－benzoyl benzoate)、4－(甲基苯硫基)－苯基－苯基甲烷(4－(methyl phenylthio)－phenyl－phenylmethane)、2,4－二乙基噻噸酮(2,4－diethyl thioxanthone)、2－氯噻噸酮(2－chlorothio－xanthone)、二苯酮(benzophenone)、乙基蒽醌(ethylanthra－quinone)等化合物。The photopolymerization initiator may be used in combination with a sensitizer (for example, a photosensitizer), a hardening accelerator, or the like as needed, and specific examples thereof include 4-dimethylamino bezophenone. ), isobutyl thioxanthone, methyl-o-benzoyl benzoate, 4-(methylphenylthio)-phenyl-phenyl 4-(methyl phenylthio)-phenyl-phenylmethane, 2,4-diethyl thioxanthone, 2-chlorothio-xanthone, benzophenone (benzophenone), a compound such as ethylanthra-quinone.
前述光聚合起始劑的含量以相對於感光性樹脂組成物占0.05~5重量%為佳，較佳為1~2重量%。前述光聚合起始劑的含量如果不及0.05重量%，則因低感度之故而難以實現正常的圖案，圖案的平直性也不好。而，前述光聚合起始劑的含量如果超過5重量%，則因感度太好而會在圖案表面上產生壓紋(embossing)，對溶劑的溶解性以及保存安定性上都有發生問題的情形。The content of the photopolymerization initiator is preferably from 0.05 to 5% by weight, preferably from 1 to 2% by weight, based on the photosensitive resin composition. When the content of the photopolymerization initiator is less than 0.05% by weight, it is difficult to achieve a normal pattern due to low sensitivity, and the flatness of the pattern is also poor. On the other hand, when the content of the photopolymerization initiator is more than 5% by weight, embossing occurs on the surface of the pattern due to the sensitivity, and there are problems in solubility in a solvent and storage stability. .
另外，本發明之彩色濾光片用感光性樹脂組成物中，E)前述矽表面添加劑係如前述之定義。此外，可以進一步包含用以提高和顏料的分散性之分散劑，或用以提高塗布性之添加劑；此等添加劑的含量可以相對於全體彩色濾光片用感光性樹脂組成物使用0.1~2重量%。Further, in the photosensitive resin composition for a color filter of the present invention, the above-mentioned enamel surface additive is as defined above. Further, a dispersing agent for improving the dispersibility of the pigment or an additive for improving the coating property may be further included; the content of the additives may be 0.1 to 2 by weight with respect to the photosensitive resin composition for the entire color filter. %.
此外，本發明之彩色濾光片用感光性樹脂中，前述F)溶劑可依溶解性、顏料分散性、塗布性而作選擇，具體而言以乙二醇甲醚醋酸酯(ethyleneglycol monomethylether acetate)、丙二醇甲醚(propyleneglycol monomethylether)、丙二醇甲醚醋酸酯(propyleneglycol monomethylether acetate)、丙二醇甲基***酯酸酯(propyleneglycol methyl monoethylether acetate)、二乙二醇二甲醚(diethyleneglycol dimethylether)、二乙二醇甲***(diethyleneglycol methyl－ethylether)、環己酮(cyclohexanone)、3－甲氧基丙酸乙酯(3－methoxy propionic acid ethyl)、3－乙氧基丙酸甲酯(3－ethoxy propionic acid methyl)、3－乙氧基丙酸乙酯(3－ethoxy propionic acid ethyl)等為佳，其等可單獨或混合2種以上作使用。前述溶劑的含量係以除去前述各成分的殘量而存在為佳，相對於全體感光性樹脂組成物以20~70重量%為宜。Further, in the photosensitive resin for a color filter of the present invention, the solvent of the F) may be selected depending on solubility, pigment dispersibility, and coatability, specifically, ethyleneglycol monomethylether acetate. , propyleneglycol monomethylether, propyleneglycol monomethylether acetate, propyleneglycol methyl monoethylether acetate, diethyleneglycol dimethylether, diethylene glycol Diethyleneglycol methyl-ethylether, cyclohexanone, 3-methoxy propionic acid ethyl, 3-ethoxy propionic acid methyl And 3-ethoxy propionic acid ethyl or the like is preferable, and these may be used alone or in combination of two or more. The content of the solvent is preferably such that the residual amount of each component is removed, and it is preferably 20 to 70% by weight based on the entire photosensitive resin composition.
再者，本發明提供一種液晶顯示器彩色濾光片之製造方法，特徵在於其包含將前述彩色濾光片用感光性樹脂組成物塗布於基板的步驟，在將前述彩色濾光片用感光性樹脂組成物塗布於基板的過程前後，當然也可以應用一般的彩色濾光片之製造方法中所使用的步驟。尤其，本發明之液晶顯示器彩色濾光片的製造方法可以提高塗布性，使發生在被旋轉塗布於基板上之光阻膜的周緣部分之不必要的EB部分最少化，可以在製造液晶顯示器彩色濾光片時省略EBR步驟，藉而突破性地減低製造成本。Furthermore, the present invention provides a method of producing a color filter for a liquid crystal display, comprising the step of applying a photosensitive resin composition for a color filter to a substrate, and using the photosensitive resin for the color filter. Before and after the process of applying the composition to the substrate, it is of course also possible to apply the steps used in the method of manufacturing a general color filter. In particular, the method for producing a color filter of a liquid crystal display of the present invention can improve coating properties, minimize unnecessary EB portions occurring in a peripheral portion of a photoresist film that is spin-coated on a substrate, and can be used to manufacture color of a liquid crystal display. The EBR step is omitted when the filter is used, thereby drastically reducing the manufacturing cost.
以下將以實施例為基礎詳細說明本發明，惟本發明並不受限於下述實施例。下述實施例中，若未另外提及，則百分率及混合比皆是以重量為基準。The invention will be described in detail below on the basis of the examples, but the invention is not limited to the following examples. In the following examples, the percentages and mixing ratios are based on weight unless otherwise mentioned.
將，A)鹼可溶性接著劑為25重量%之甲基丙烯酸苄酯(benzyl methacrylate)/甲基丙烯酸/丙烯酸羥乙基肉桂酯(hydroxyethylcinnamic acrylate)之共聚物(在丙二醇甲醚醋酸酯的溶液中之共聚合比為60/20/20，固形分的含量為35重量%，重量平均分子量為30,000之共聚物)；B)至少具有2個以上之乙烯系雙鍵的交聯性單體為5重量%之二異戊四醇六丙烯酸酯(dipentaerythritol hexaacylate)；C)顏料為22重量%之C.I.pigment red 254及C.I.pigment yellow 138；D)光聚合起始劑為1重量%之Irgacure 369(Ciba Special Chemicals製)、0.5重量%之4,4－雙二乙氨基二苯甲酮及0.5重量%之2,4－二乙基噻噸酮；E)前述矽系表面添加劑為0.4重量%之聚醚變形而成的聚二甲基矽氧烷高分子溶液及聚氧化烯烴聚二甲基矽氧烷高分子(但是，此處該二種類之添加劑含有成分比率為1：1)；以及，以殘量含有F)溶劑係由丙二醇甲醚醋酸酯環己酮以3：1的比例混合而成之混合溶劑後，將其等混合以製成液狀之彩色濾光片用感光性樹脂組成物。The A) alkali-soluble binder is a copolymer of 25% by weight of benzyl methacrylate/methacrylic acid/hydroxyethylcinnamic acrylate (in a solution of propylene glycol methyl ether acetate) The copolymerization ratio is 60/20/20, the content of the solid content is 35% by weight, and the copolymer having a weight average molecular weight of 30,000); B) the crosslinkable monomer having at least two ethylene double bonds is 5 Dipentaerythritol hexaacylate; C) Pigment 22% by weight CIpigment red 254 and CIpigment yellow 138; D) Photopolymerization initiator 1% by weight Irgacure 369 (Ciba Special Chemicals), 0.5% by weight of 4,4-bisdiethylaminobenzophenone and 0.5% by weight of 2,4-diethylthioxanthone; E) the above-mentioned lanthanide surface additive is 0.4% by weight a polydimethyl methoxy hydride polymer solution obtained by deforming ether and a polyoxyalkylene polydimethyl siloxane polymer (however, the additive of the two types contains a composition ratio of 1:1); The residual amount of F) solvent is propylene glycol methyl ether acetate cyclohexanone ratio of 3:1 After mixing the mixed solvent, mixing the like to which a color filter is made of a liquid photosensitive resin composition thereof.
以和前述實施1同樣的組成和含量進行製造，混合0.5重量%之聚醚變形而成的聚二甲基矽氧烷高分子溶液作為E)矽系表面添加劑，製成液狀之彩色濾光片用感光性樹脂組成物。Manufactured in the same composition and content as in the above-mentioned Embodiment 1, a polydimethylaphthalene polymer solution obtained by mixing 0.5% by weight of a polyether was mixed as an E) lanthanoid surface additive to prepare a liquid color filter. The sheet is made of a photosensitive resin composition.
以和前述實施1同樣的組成和含量進行製造，混合0.5重量%之聚氧化烯烴聚二甲基矽氧烷高分子作為E)矽系表面添加劑，製成液狀之彩色濾光片用感光性樹脂組成物。Manufactured in the same composition and content as in the above-mentioned Embodiment 1, a 0.5% by weight polyoxyalkylene polydimethyl siloxane polymer was mixed as an E) lanthanoid surface additive to prepare a liquid color filter for photosensitivity. Resin composition.
以和前述實施1同樣的組成和含量進行製造，混合0.2重量%之聚醚變形而成的聚二甲基矽氧烷高分子溶液作為E)矽系表面添加劑，製成液狀之彩色濾光片用感光性樹脂組成物。Manufactured in the same composition and content as in the above-mentioned Embodiment 1, a polydimethyl methoxy hydride polymer solution obtained by mixing 0.2% by weight of a polyether was mixed as an E) lanthanoid surface additive to prepare a liquid color filter. The sheet is made of a photosensitive resin composition.
以和前述實施1同樣的組成和含量進行製造，使用0.5重量%之氟系添加劑BYK－340(BYK－Chemi製造)取代E)矽系表面添加劑，製成感光性樹脂組成物。The composition was prepared in the same manner and in the same manner as in the above-mentioned Example 1, and a 0.5% by weight fluorine-based additive BYK-340 (manufactured by BYK-Chemi) was used instead of the E) fluorene-based surface additive to prepare a photosensitive resin composition.
以和前述實施1同樣的組成和含量進行製造，使用0.5重量%之丙烯酸酯系添加劑BYK－354(BYK－Chemi製造)取代E)矽系表面添加劑，製成感光性樹脂組成物。The composition was prepared in the same manner and in the same manner as in the above-mentioned Example 1, and a 0.5% by weight of an acrylate-based additive BYK-354 (manufactured by BYK-Chemi) was used instead of the E) fluorene-based surface additive to prepare a photosensitive resin composition.
將改變前述矽系及非矽系添加劑的種類及含量而得到之實施例1~4及比較例1和比較例2進行塗布特性的比較。The coating properties of Examples 1 to 4 and Comparative Example 1 and Comparative Example 2 obtained by changing the types and contents of the above-mentioned lanthanide and non-antimony-based additives were compared.
實驗方法係將依據前述實施例1~4和比較例1及比較例2所製得之感光性樹脂組成物，在玻璃基板上滴下0.8cc並以300 rpm旋轉塗布後，在90℃的熱板上利用預烤使之乾燥，得到塗布膜，再測定經過旋轉塗布的基板在周緣上之不必要的EB部分之厚度及寬度。測定結果示於下表1。The experimental method is based on the photosensitive resin composition prepared in the above Examples 1 to 4 and Comparative Example 1 and Comparative Example 2, and 0.8 cc was dropped on a glass substrate and spin-coated at 300 rpm, followed by a hot plate at 90 ° C. The film was dried by prebaking to obtain a coating film, and the thickness and width of the unnecessary EB portion on the periphery of the spin-coated substrate were measured. The results of the measurements are shown in Table 1 below.
如前述表1所示，實施例1~4的情形和比較例1及2相比，經過塗布的基板在周緣上之不必要的膜部分(EB)寬度和厚度都相對地顯示出減少的結果，塗布後之整體的膜狀態也都是幾乎沒有塗布沾污的良好狀態。與此相反地，比較例1及2的情形，EB寬度和厚度與實施例1相比，觀察到分別大了2倍左右，而塗布時也觀察到若干的塗布沾污情形。此種比較例1及2，因為EB部分的厚度厚，所以在一般的顯像步驟中對於光阻膜的完全除去是不利的。據此可知，實施例1~4的情形和比較例1、2相比時，在旋轉塗布時的塗布性能上是優良的。As shown in the above Table 1, in the cases of Examples 1 to 4, the unnecessary film portion (EB) width and thickness on the peripheral edge of the coated substrate were relatively reduced as compared with Comparative Examples 1 and 2. The overall film state after coating is also in a good state with almost no coating contamination. On the contrary, in the cases of Comparative Examples 1 and 2, the EB width and the thickness were observed to be about 2 times larger than those of Example 1, and a number of coating stains were observed during coating. In Comparative Examples 1 and 2, since the thickness of the EB portion was thick, it was disadvantageous for the complete removal of the photoresist film in the general development step. From this, it can be seen that in the cases of Examples 1 to 4, compared with Comparative Examples 1 and 2, the coating performance at the time of spin coating was excellent.
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| JP5042539B2 (en) * | 2006-06-22 | 2012-10-03 | 東京応化工業株式会社 | Photosensitive resin composition and liquid crystal alignment control bump using the same |
| KR100865227B1 (en) * | 2006-08-18 | 2008-10-23 | 제이에스알 가부시끼가이샤 | Pigment Resin Compositions, Resin Compositions for Ink Jet Color Filters, Color Filters, and Liquid Crystal Display Devices |
| KR100718895B1 (en) * | 2006-08-21 | 2007-05-16 | 금호석유화학 주식회사 | Thermosetting resin composition for over coat film of a color filter and over coat film thereof |
| KR101306153B1 (en) | 2006-08-25 | 2013-09-10 | 주식회사 동진쎄미켐 | Photosensitive resin composition |
| CN101178541B (en) * | 2006-10-31 | 2012-04-25 | 三洋化成工业株式会社 | Photosensitive resin composition |
| KR101482652B1 (en) * | 2007-06-07 | 2015-01-16 | 주식회사 동진쎄미켐 | Passivation composition for organic semiconductor |
| JP5340623B2 (en) * | 2008-03-31 | 2013-11-13 | 富士フイルム株式会社 | Photosensitive resin composition, light-shielding color filter, method for producing the same, and solid-state imaging device |
| JP5079583B2 (en) * | 2008-04-23 | 2012-11-21 | 大日本印刷株式会社 | Photosensitive colored resin composition, color filter using the same, and display device including the color filter |
| WO2010092688A1 (en) * | 2009-02-16 | 2010-08-19 | 富士電機ホールディングス株式会社 | Process for producing color conversion filter |
| TWI467336B (en) * | 2012-10-08 | 2015-01-01 | Everlight Chem Ind Corp | Black photosensitive resin composition and light-blocking layer using the same |
| KR101443757B1 (en) * | 2010-11-08 | 2014-09-25 | 제일모직 주식회사 | Photosensitive resin composition for color filter and color filter using same |
| TWI444766B (en) * | 2012-03-16 | 2014-07-11 | Chi Mei Corp | Photosensitive resin composition and uses thereof |
| JP6466087B2 (en) * | 2013-06-14 | 2019-02-06 | アーゼッド・エレクトロニック・マテリアルズ（ルクセンブルグ）ソシエテ・ア・レスポンサビリテ・リミテ | Negative photosensitive composition that can be cured at low temperature |
| CN105301916A (en) * | 2015-11-16 | 2016-02-03 | 北京中科紫鑫科技有限责任公司 | Method for forming photoresist pattern |
| CN105301901A (en) * | 2015-11-16 | 2016-02-03 | 北京中科紫鑫科技有限责任公司 | Preparation method of positive photoresist composition |
| KR102334956B1 (en) | 2018-11-01 | 2021-12-02 | 주식회사 엘지화학 | Ramp for vehicle and manufacturing method of same |
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| US20030224286A1 (en) * | 2002-03-03 | 2003-12-04 | Shipley Company, L.L.C. | Processes for producing polysiloxanes and photoresist compositions comprising same |
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