JP2008020602A - Black-colored composition for color filter, and the color filter - Google Patents
Black-colored composition for color filter, and the color filter Download PDFInfo
- Publication number
- JP2008020602A JP2008020602A JP2006191352A JP2006191352A JP2008020602A JP 2008020602 A JP2008020602 A JP 2008020602A JP 2006191352 A JP2006191352 A JP 2006191352A JP 2006191352 A JP2006191352 A JP 2006191352A JP 2008020602 A JP2008020602 A JP 2008020602A
- Authority
- JP
- Japan
- Prior art keywords
- transparent resin
- photosensitive transparent
- black
- parts
- color filter
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
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Landscapes
- Materials For Photolithography (AREA)
- Liquid Crystal (AREA)
- Optical Filters (AREA)
Abstract
Description
本発明は、高感度の感光性着色組成物に関するものであり、特にカラー液晶表示装置、カラー撮像管素子等に用いられるカラーフィルタの製造に使用される高感度なカラーフィルタ用黒色着色組成物、およびこれを用いて形成されるカラーフィルタに関するものである。 The present invention relates to a highly sensitive photosensitive coloring composition, and particularly a highly sensitive black coloring composition for a color filter used for producing a color filter used for a color liquid crystal display device, a color image pickup tube element, and the like. And a color filter formed using the same.
カラーフィルタは、ガラス等の透明な基板の表面に2種以上の異なる色相の微細な帯(ストライプ)状のフィルタセグメントを平行または交差して配置したもの、あるいは微細なフィルタセグメントを縦横一定の配列で配置したものからなっている。フィルタセグメントは、数ミクロン〜数100ミクロンと微細であり、色相毎に所定の配列で整然と配置されている。 A color filter has two or more kinds of fine band (striped) filter segments arranged in parallel or intersecting with each other on the surface of a transparent substrate such as glass, or the fine filter segments are arranged vertically and horizontally. It is made up of those arranged in The filter segments are as fine as several microns to several hundreds of microns, and are regularly arranged in a predetermined arrangement for each hue.
一般的に、カラー液晶表示装置では、カラーフィルタの上に液晶を駆動させるための透明電極が蒸着あるいはスパッタリングにより形成され、さらにその上に液晶を一定方向に配向させるための配向膜が形成されている。これらの透明電極および配向膜の性能を十分に得るには、その形成を一般に200℃以上、好ましくは230℃以上の高温で行う必要がある。 Generally, in a color liquid crystal display device, a transparent electrode for driving a liquid crystal is formed on a color filter by vapor deposition or sputtering, and an alignment film for aligning the liquid crystal in a certain direction is further formed thereon. Yes. In order to sufficiently obtain the performance of these transparent electrodes and alignment films, the formation thereof must generally be performed at a high temperature of 200 ° C. or higher, preferably 230 ° C. or higher.
このため、現在、カラーフィルタの製造に用いられるカラーフィルタ用着色組成物の製造方法としては、耐光性、耐熱性に優れる顔料を着色材とする顔料分散法と呼ばれる方法が主流となっている。 For this reason, at present, as a method for producing a colored composition for a color filter used for producing a color filter, a method called a pigment dispersion method using a pigment having excellent light resistance and heat resistance as a colorant is mainly used.
顔料分散法の場合、感光性樹脂組成物中に顔料を分散した感光性着色組成物(顔料レジスト材)をガラス等の透明基板に塗布し、乾燥により溶剤を除去した後、一つのフィルタ色のパターン露光を行い、次いで未露光部を現像工程で除去して1色目のパターンを形成、必要に応じて加熱等の処理を加えた後、同様の操作を全フィルタ色について順次繰り返すことによりカラーフィルタを製造することができる。 In the case of the pigment dispersion method, a photosensitive coloring composition (pigment resist material) in which a pigment is dispersed in a photosensitive resin composition is applied to a transparent substrate such as glass, and the solvent is removed by drying. Perform pattern exposure, then remove the unexposed area in the development process to form the pattern for the first color, apply heat and other treatments as necessary, and then repeat the same operation for all filter colors in sequence. Can be manufactured.
顔料を含む感光性着色組成物を用いたフィルタセグメント形成において、高い感光性、非画像部の現像液に対する溶解性、及び画像部の耐薬品性は重要な特性である。近年では、より色濃度の高いカラーフィルタや光学濃度(OD値)の高いブラックマトリクスの要求が高まっており、感光性着色組成物における着色材濃度が高くなる傾向にある。しかし、着色材濃度が上昇すると、着色材自身の光吸収の増加により露光部の十分な硬化が得られない等、他の特性に対して影響を及ぼす。このように、着色材濃度の上昇と、感光性を始めとする感光性樹脂組成物由来の特性の維持とは、トレードオフの関係にある。 In forming a filter segment using a photosensitive coloring composition containing a pigment, high photosensitivity, solubility in a developer in a non-image area, and chemical resistance in an image area are important characteristics. In recent years, there has been an increasing demand for color filters with higher color density and black matrix with higher optical density (OD value), and there is a tendency for the colorant density in photosensitive coloring compositions to increase. However, when the colorant concentration is increased, other characteristics such as an insufficient curing of the exposed portion cannot be obtained due to an increase in light absorption of the colorant itself. Thus, there is a trade-off relationship between the increase in the colorant concentration and the maintenance of characteristics derived from the photosensitive resin composition including the photosensitivity.
感光性と現像液に対する溶解性を高めるため、側鎖にエチレン性不飽和二重結合およびカルボキシル基を有する感光性透明樹脂を用いたカラーフィルタ用感光性着色組成物が知られている。これを感光性樹脂組成物として用いるためには、感光性透明樹脂を構成する単量体の種類や比率を調整して、安定性、溶解性、及び耐薬品性などの多くの特性を満たす設計が必要となる。 In order to improve the photosensitivity and the solubility in a developer, a photosensitive coloring composition for a color filter using a photosensitive transparent resin having an ethylenically unsaturated double bond and a carboxyl group in the side chain is known. In order to use this as a photosensitive resin composition, the type and ratio of monomers constituting the photosensitive transparent resin are adjusted to satisfy many characteristics such as stability, solubility, and chemical resistance. Is required.
そして、感光性着色組成物において、着色材の分散安定性を維持しつつ、高濃度化に伴う感光性着色組成物の高感度化、良好なパターニング性(未露光部分の溶解性、光硬化部分の形状維持など)を達成することは、感光性透明樹脂の設計変更だけでは限界にきている。
そこで本発明は、高感度と優れた分散安定性、パターニング性、耐薬品性等の物性の維持とを両立したカラーフィルタ用黒色着色組成物、およびこれを用いたカラーフィルタを提供することを目的とする。 Therefore, the present invention has an object to provide a black coloring composition for a color filter that achieves both high sensitivity and excellent dispersion stability, patterning properties, maintenance of physical properties such as chemical resistance, and a color filter using the same. And
本発明のカラーフィルタ用黒色着色組成物は、感光性透明樹脂、非感光性透明樹脂、4つ以上のエチレン性不飽和二重結合を有する多官能モノマー、および黒色着色材を含有する黒色着色組成物であって、該黒色着色組成物中のエチレン性不飽和二重結合の重量モル濃度が、感光性透明樹脂、非感光性透明樹脂、および多官能モノマーの合計重量を基準として1.6×10-3mol/g 〜6.6×10-3mol/gであることを特徴とする。 The black coloring composition for a color filter of the present invention is a black coloring composition containing a photosensitive transparent resin, a non-photosensitive transparent resin, a polyfunctional monomer having four or more ethylenically unsaturated double bonds, and a black coloring material. The weight molar concentration of the ethylenically unsaturated double bond in the black coloring composition is 1.6 × based on the total weight of the photosensitive transparent resin, the non-photosensitive transparent resin, and the polyfunctional monomer. 10 −3 mol / g to 6.6 × 10 −3 mol / g.
また、本発明のカラーフィルタは、前記カラーフィルタ用黒色着色組成物を用いて形成されるブラックマトリックスを具備することを特徴とする。 Moreover, the color filter of this invention comprises the black matrix formed using the said black coloring composition for color filters, It is characterized by the above-mentioned.
本発明のカラーフィルタ用黒色着色組成物は、感光性透明樹脂、非感光性透明樹脂、および多官能モノマーを必須成分とし、光反応性部位の濃度がコントロールされているため、カラーフィルタ用黒色着色組成物としての分散安定性、高感度、優れたパターニング性、耐薬品性を達成することができる。 The black coloring composition for a color filter of the present invention has a photosensitive transparent resin, a non-photosensitive transparent resin, and a polyfunctional monomer as essential components, and the concentration of the photoreactive site is controlled. Dispersion stability, high sensitivity, excellent patterning properties, and chemical resistance as a composition can be achieved.
また、本発明のカラーフィルタ用黒色着色組成物は、従来のカラーフィルタ用黒色着色組成物より溶剤耐性が高く、高感度であるために少ない露光量にて十分に硬化し、生産性にも優れている。よって、本発明のカラーフィルタ用黒色着色組成物を用いてブラックマトリックスを形成することにより、安定して高品質の透過型・反射型のカラー液晶表示装置ならびに固体撮像素子の色分解用カラーフィルタを製造することができる。 In addition, the black coloring composition for color filters of the present invention has higher solvent resistance than conventional black coloring compositions for color filters and is highly sensitive, so it can be cured sufficiently with a small amount of exposure and has excellent productivity. ing. Therefore, by forming a black matrix using the black coloring composition for a color filter of the present invention, a stable and high-quality transmissive / reflective color liquid crystal display device and a color filter for color separation of a solid-state image sensor are obtained. Can be manufactured.
まず、本発明のカラーフィルタ用黒色着色組成物について説明する。
本発明のカラーフィルタ用黒色着色組成物は、感光性透明樹脂、非感光性透明樹脂、4つ以上のエチレン性不飽和二重結合を有する多官能モノマー、および黒色着色材を含有する。
First, the black coloring composition for color filters of this invention is demonstrated.
The black coloring composition for color filters of the present invention contains a photosensitive transparent resin, a non-photosensitive transparent resin, a polyfunctional monomer having four or more ethylenically unsaturated double bonds, and a black coloring material.
そして、本発明の黒色着色組成物中のエチレン性不飽和二重結合重量モル濃度は、感光性透明樹脂、非感光性透明樹脂、および多官能モノマーの合計(以下、感光性透明樹脂、非感光性透明樹脂、および多官能モノマーからなる組成物を感光性樹脂組成物という。)重量を基準として下記数式(I)から算出される値であり、1.6×10-3mol/g 〜6.6×10-3mol/g、好ましくは2.6×10-3mol/g 〜5.5×10-3mol/g、更に好ましくは2.7×10-3mol/g 〜4.5×10-3mol/gである。
数式(I):
(エチレン性不飽和二重結合重量モル濃度)=(感光性透明樹脂の重量/感光性透明樹脂の二重結合当量+多官能モノマーの重量/多官能モノマーの二重結合当量)/(感光性透明樹脂の重量+非感光性透明樹脂の重量+多官能モノマーの重量)
なお、二重結合当量とは、下記数式(II)で定義され、分子中に含まれる二重結合量の尺度となるものであり、同じ分子量の化合物であれば、二重結合当量の数値が小さいほど二重結合の導入量が多くなる。
数式(II):
[二重結合当量]=[繰り返し構成単位の分子量]/[繰り返し構成単位中の二重結合の数]
黒色着色組成物中のエチレン性不飽和二重結合重量モル濃度が1.6×10-3mol/gより低い場合には、感光性が低下し、黒色着色塗膜を形成する場合に十分な硬化性が得られない。また、黒色着色組成物中のエチレン性不飽和二重結合重量モル濃度が6.6×10-3mol/gよりも高い場合には、感度は高いが、分散安定性が低下して均一な黒色着色塗膜が得られなくなったり、現像性が低下したりし、パターニング性が低下する場合がある。
The ethylenically unsaturated double bond weight molar concentration in the black coloring composition of the present invention is the sum of photosensitive transparent resin, non-photosensitive transparent resin, and polyfunctional monomer (hereinafter referred to as photosensitive transparent resin, non-photosensitive). A composition comprising a transparent transparent resin and a polyfunctional monomer is referred to as a photosensitive resin composition.) A value calculated from the following formula (I) based on the weight, and 1.6 × 10 −3 mol / g to 6 .6 × 10 −3 mol / g, preferably 2.6 × 10 −3 mol / g to 5.5 × 10 −3 mol / g, more preferably 2.7 × 10 −3 mol / g to 4. 5 × 10 −3 mol / g.
Formula (I):
(Ethylene unsaturated double bond weight molar concentration) = (Weight of photosensitive transparent resin / Double bond equivalent of photosensitive transparent resin + Weight of polyfunctional monomer / Double bond equivalent of polyfunctional monomer) / (Photosensitivity) (Weight of transparent resin + weight of non-photosensitive transparent resin + weight of polyfunctional monomer)
The double bond equivalent is defined by the following formula (II) and is a measure of the amount of double bonds contained in the molecule. If the compounds have the same molecular weight, the value of the double bond equivalent is The smaller the amount, the greater the amount of double bonds introduced.
Formula (II):
[Double bond equivalent] = [molecular weight of repeating structural unit] / [number of double bonds in repeating structural unit]
When the ethylenically unsaturated double bond weight molar concentration in the black colored composition is lower than 1.6 × 10 −3 mol / g, the photosensitivity is lowered, which is sufficient for forming a black colored coating film. Curability cannot be obtained. In addition, when the ethylenically unsaturated double bond weight molar concentration in the black colored composition is higher than 6.6 × 10 −3 mol / g, the sensitivity is high, but the dispersion stability is lowered and uniform. A black colored coating film may not be obtained, developability may decrease, and patterning properties may decrease.
本発明で好ましく用いられる感光性透明樹脂および非感光性透明樹脂は、可視光領域の400〜700nmの全波長領域において透過率が好ましくは80%以上、より好ましくは95%以上の樹脂である。 The photosensitive transparent resin and the non-photosensitive transparent resin preferably used in the present invention are resins having a transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region.
感光性透明樹脂は、エチレン性不飽和二重結合を有する樹脂であり、例えば、水酸基、カルボキシル基、アミノ基等の反応性の置換基を有する高分子に、イソシアネート基、アルデヒド基、エポキシ基、カルボキシル基等の反応性置換基を有する(メタ)アクリル化合物やケイヒ酸を反応させて、(メタ)アクリロイル基、スチリル基等のエチレン性不飽和二重結合を有する官能基を前記高分子に導入した樹脂が挙げられる。具体的には、水酸基を有するエチレン性不飽和単量体および他のエチレン性不飽和単量体を共重合した共重合体に、水酸基と反応可能な官能基及びエチレン性不飽和二重結合を有する化合物を反応させることにより得られるものがある。水酸基と反応可能な官能基としては、イソシアネート基、カルボキシル基等が挙げられるが、特に反応性の点でイソシアネート基が好ましく、イソシアネート基及びエチレン性不飽和二重結合を有する化合物として具体的には、2−アクリロイルエチルイソシアネート、2−メタクリロイルエチルイソシアネート等が挙げられる。また、スチレン−無水マレイン酸共重合体やα−オレフィン−無水マレイン酸共重合体等の酸無水物を含む高分子をヒドロキシアルキル(メタ)アクリレート等の水酸基を有する(メタ)アクリル化合物によりハーフエステル化したものも用いられる。
感光性透明樹脂中に水酸基などを介して導入されるエチレン性不飽和二重結合の量は、得られる感光性透明樹脂の「二重結合当量」により示される。
The photosensitive transparent resin is a resin having an ethylenically unsaturated double bond, for example, a polymer having a reactive substituent such as a hydroxyl group, a carboxyl group, an amino group, an isocyanate group, an aldehyde group, an epoxy group, A functional group having an ethylenically unsaturated double bond such as a (meth) acryloyl group or a styryl group is introduced into the polymer by reacting a (meth) acrylic compound having a reactive substituent such as a carboxyl group or cinnamic acid. Resin. Specifically, a functional group capable of reacting with a hydroxyl group and an ethylenically unsaturated double bond are added to a copolymer obtained by copolymerizing an ethylenically unsaturated monomer having a hydroxyl group and another ethylenically unsaturated monomer. Some of them are obtained by reacting the compounds they have. Examples of the functional group capable of reacting with a hydroxyl group include an isocyanate group and a carboxyl group, but an isocyanate group is particularly preferred in terms of reactivity, and specifically, a compound having an isocyanate group and an ethylenically unsaturated double bond. , 2-acryloyl ethyl isocyanate, 2-methacryloyl ethyl isocyanate and the like. In addition, a polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer is half-esterified with a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate. A modified version is also used.
The amount of the ethylenically unsaturated double bond introduced into the photosensitive transparent resin via a hydroxyl group or the like is indicated by the “double bond equivalent” of the resulting photosensitive transparent resin.
本発明における感光性透明樹脂の二重結合当量は200〜1200であることが好ましく、300〜900であることがより好ましい。感光性透明樹脂の二重結合当量が200未満の場合は、エチレン性不飽和二重結合を導入させる反応性の置換基を有するエチレン性不飽和単量体の比率が高くなり、諸特性を維持するのに十分な量の他のエチレン性不飽和単量体を共重合させることができない。1200を越える場合は、エチレン性不飽和二重結合の数が少ないため十分な感度を得ることができない。 The double bond equivalent of the photosensitive transparent resin in the present invention is preferably 200 to 1200, and more preferably 300 to 900. When the double bond equivalent of the photosensitive transparent resin is less than 200, the ratio of the ethylenically unsaturated monomer having a reactive substituent for introducing an ethylenically unsaturated double bond is increased, and various characteristics are maintained. A sufficient amount of other ethylenically unsaturated monomers cannot be copolymerized. When it exceeds 1200, sufficient sensitivity cannot be obtained because the number of ethylenically unsaturated double bonds is small.
また、感光性透明樹脂の重量平均分子量(Mw)は、黒色着色材の分散性が良好な点から、好ましくは2000〜200000、より好ましくは5000〜50000である。 Moreover, the weight average molecular weight (Mw) of the photosensitive transparent resin is preferably 2000 to 200000, more preferably 5000 to 50000, from the viewpoint of good dispersibility of the black colorant.
非感光性透明樹脂は、エチレン性不飽和二重結合を有しない樹脂であり、熱可塑性樹脂、熱硬化性樹脂がある。熱可塑性樹脂としては、例えば、ブチラール樹脂、スチレン−マレイン酸共重合体、塩素化ポリエチレン、塩素化ポリプロピレン、ポリ塩化ビニル、塩化ビニル−酢酸ビニル共重合体、ポリ酢酸ビニル、ポリウレタン系樹脂、ポリエステル樹脂、アクリル系樹脂、アルキッド樹脂、スチレン樹脂、ポリアミド樹脂、ゴム系樹脂、環化ゴム系樹脂、セルロース類、ポリブタジエン、ポリイミド樹脂等が挙げられる。また、熱硬化性樹脂としては、例えば、エポキシ樹脂、ベンゾグアナミン樹脂、ロジン変性マレイン酸樹脂、ロジン変性フマル酸樹脂、フェノール樹脂、メラミン樹脂、尿素樹脂等が挙げられる。 The non-photosensitive transparent resin is a resin that does not have an ethylenically unsaturated double bond, and includes a thermoplastic resin and a thermosetting resin. Examples of the thermoplastic resin include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, and polyester resin. , Acrylic resins, alkyd resins, styrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polybutadiene, polyimide resins, and the like. Examples of the thermosetting resin include an epoxy resin, a benzoguanamine resin, a rosin-modified maleic acid resin, a rosin-modified fumaric acid resin, a phenol resin, a melamine resin, and a urea resin.
本発明の黒色着色組成物を用いてアルカリ現像によりブラックマトリックスを形成する場合には、非感光性透明樹脂として、アルカリ可溶型のものを用いることが好ましい。アルカリ可溶型の非感光性透明樹脂とは、アルカリ水溶液に溶解する性質を持つ、エチレン性不飽和二重結合を有しない透明樹脂であり、例えば、カルボキシル基、スルホン基などの酸性官能基を有する重量平均分子量1000〜500000、好ましくは5000〜100000の非樹脂感光性透明樹脂が挙げられる。酸性官能基の中では、カルボキシル基が好ましい。カラーフィルタ用黒色着色組成物の分散安定化を図るためには、感光性透明樹脂の酸価と、非感光性透明樹脂の酸価の差の絶対値が100未満であることが好ましく、より好ましくは80未満であり、さらに好ましくは50未満である。このバランスにおいて、カラーフィルタ用黒色着色組成物の経時安定性が保たれ、黒色着色塗膜のパターニング性も良好となり、安定した形状のブラックマトリックスが得られる。アルカリ可溶型の非感光性透明樹脂として具体的には、酸性官能基を有するアクリル樹脂、α−オレフィン/(無水)マレイン酸共重合体、スチレン/(無水)マレイン酸共重合体、スチレン/スチレンスルホン酸共重合体、エチレン/(メタ)アクリル酸共重合体、イソブチレン/(無水)マレイン酸共重合体などが挙げられる。なかでも、酸性官能基を有するアクリル樹脂、α−オレフィン/(無水)マレイン酸共重合体、スチレン/(無水)マレイン酸共重合体およびスチレン/スチレンスルホン酸共重合体から選ばれる少なくとも1種の樹脂、特に酸性官能基を有するアクリル樹脂は、耐熱性、透明性が高いため、好適に用いられる。 When forming a black matrix by alkali development using the black coloring composition of the present invention, it is preferable to use an alkali-soluble type as the non-photosensitive transparent resin. The alkali-soluble non-photosensitive transparent resin is a transparent resin having a property of dissolving in an alkaline aqueous solution and having no ethylenically unsaturated double bond. For example, an acidic functional group such as a carboxyl group or a sulfone group A non-resin photosensitive transparent resin having a weight average molecular weight of 1,000 to 500,000, preferably 5,000 to 100,000 is mentioned. Of the acidic functional groups, a carboxyl group is preferred. In order to stabilize the dispersion of the black coloring composition for a color filter, the absolute value of the difference between the acid value of the photosensitive transparent resin and the acid value of the non-photosensitive transparent resin is preferably less than 100, more preferably Is less than 80, more preferably less than 50. In this balance, the black color composition for color filters is kept stable over time, the patterning property of the black colored coating film is also improved, and a black matrix having a stable shape is obtained. Specific examples of the alkali-soluble non-photosensitive transparent resin include acrylic resin having an acidic functional group, α-olefin / (anhydrous) maleic acid copolymer, styrene / (anhydrous) maleic acid copolymer, styrene / Examples thereof include styrene sulfonic acid copolymers, ethylene / (meth) acrylic acid copolymers, and isobutylene / (anhydrous) maleic acid copolymers. Among them, at least one selected from an acrylic resin having an acidic functional group, an α-olefin / (anhydrous) maleic acid copolymer, a styrene / (anhydrous) maleic acid copolymer, and a styrene / styrene sulfonic acid copolymer. Resins, particularly acrylic resins having an acidic functional group, are preferably used because of their high heat resistance and transparency.
また、黒色着色材として顔料を用いる場合には、感光性透明樹脂または非感光性透明樹脂が重合成分として下記式(1)で示されるエチレン性不飽和単量体(a)を含むことが、顔料の分散安定性向上という面から好ましい。
式(1):
Moreover, when using a pigment as a black coloring material, the photosensitive transparent resin or the non-photosensitive transparent resin contains an ethylenically unsaturated monomer (a) represented by the following formula (1) as a polymerization component. This is preferable from the viewpoint of improving the dispersion stability of the pigment.
Formula (1):
上記式(1)において、R2のアルキレン基の炭素数は、2〜3であることが好ましい。また、R3のアルキル基の炭素数は1〜20であるが、より好ましくは1〜10であり、R3のアルキル基はベンゼン環を含んでもよい。R3のアルキル基の炭素数が1〜10のときはアルキル基が障害となり樹脂同士の接近を抑制し、顔料への吸着/配向を促進するが、炭素数が10を超えると、アルキル基の立体障害効果が高くなり、ベンゼン環の顔料への吸着/配向までをも妨げる傾向を示す。この傾向は、R3のアルキル基の炭素鎖長が長くなるに従い顕著となり、炭素数が20を超えると、ベンゼン環の吸着/配向が極端に低下する。R3で表されるベンゼン環を含むアルキル基としては、ベンジル基、2−フェニル(イソ)プロピル基等を挙げることができる。
In the above formula (1), the number of carbon atoms in the alkylene group R 2 is preferably 2-3. Although the carbon number of the alkyl group of R 3 is 1 to 20, more preferably 1 to 10, alkyl group of R 3 may include a benzene ring. When the carbon number of the alkyl group of R 3 is 1 to 10, the alkyl group becomes an obstacle and suppresses the approach between the resins and promotes adsorption / orientation to the pigment, but when the carbon number exceeds 10, The steric hindrance effect becomes high and shows a tendency to prevent even adsorption / orientation of the benzene ring to the pigment. This tendency becomes more prominent as the carbon chain length of the alkyl group of R 3 becomes longer. When the carbon number exceeds 20, the adsorption / orientation of the benzene ring is extremely reduced. Examples of the alkyl group containing a benzene ring represented by R 3 include a benzyl group and a 2-phenyl (iso) propyl group.
エチレン性不飽和単量体(a)としては、フェノールのエチレンオキサイド(EO)変性(メタ)アクリレート、パラクミルフェノールのEOまたはプロピレンオキサイド(PO)変性(メタ)アクリレート、ノニルフェノールのEO変性(メタ)アクリレート、ノニルフェノールのPO変性(メタ)アクリレート等が挙げられる。これら化合物のうち、パラクミルフェノールのEOまたはPO変性(メタ)アクリレートは、上記ベンゼン環のπ電子の効果ばかりでなく、その立体的な効果も加わり、顔料などの着色材に対してより良好な吸着/配向面を形成することができるので、より分散効果が高い。 Examples of the ethylenically unsaturated monomer (a) include phenol ethylene oxide (EO) modified (meth) acrylate, paracumylphenol EO or propylene oxide (PO) modified (meth) acrylate, and nonylphenol EO modified (meth). Examples thereof include acrylate, PO-modified (meth) acrylate of nonylphenol, and the like. Among these compounds, EO or PO-modified (meth) acrylate of paracumylphenol is not only effective for the π-electron of the benzene ring, but also its steric effect, which is better for coloring materials such as pigments. Since the adsorption / orientation plane can be formed, the dispersion effect is higher.
エチレン性不飽和単量体(a)と共重合可能な他のエチレン性不飽和単量体化合物(b)としては、(メタ)アクリル酸、メチル(メタ)アクリレート、エチル(メタ)アクリレート、(イソ)プロピル(メタ)アクリレート、(イソ)ブチル(メタ)アクリレート、(イソ)ペンチル(メタ)アクリレート、2−ヒドロキシエチル(メタ)アクリレート、2−ヒドロキシプロピル(メタ)アクリレート、ベンジル(メタ)アクリレート、シクロヘキシル(メタ)アクリレート、グリシジル(メタ)アクリレート、イソボニル(メタ)アクリレート、アシッドホスホオキシエチル(メタ)アクリレート、アシッドホスホオキシプロピル(メタ)アクリレート、3−クロロ−2−アシッドホスホオキシエチル(メタ)アクリレート、アシッドホスホオキシポリエチレングリコールモノ(メタ)アクリレート等が挙げられ、これらを1種または2種以上用いることができる。 Other ethylenically unsaturated monomer compounds (b) copolymerizable with the ethylenically unsaturated monomer (a) include (meth) acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, ( Iso) propyl (meth) acrylate, (iso) butyl (meth) acrylate, (iso) pentyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, benzyl (meth) acrylate, Cyclohexyl (meth) acrylate, glycidyl (meth) acrylate, isobornyl (meth) acrylate, acid phosphooxyethyl (meth) acrylate, acid phosphooxypropyl (meth) acrylate, 3-chloro-2-acid phosphooxyethyl (meth) acrylate , Acidho Like e oxy polyethylene glycol mono (meth) acrylate. These may be used alone or in combination.
上記一般式(1)で示表されるエチレン性不飽和単量体化合物(a)と他のエチレン性不飽和単量体二重結合を有する化合物(b)とを共重合してなる感光性透明樹脂または非感光性透明樹脂中の単量体化合物(a)の共重合比率割合は、(a)および(b)を合わせた単量体の全量を基準として0.1〜50重量%を占めるのが好ましく、より好ましくは10〜35重量%である。単量体(a)の共重合比率が0.1重量%より少ないと、顔料の分散効果が低下する。また、50重量%より多いと疎水性が大きくなり、黒色着色組成物の現像性が低下したり、残渣の原因になったりすることがある。 Photosensitivity obtained by copolymerizing the ethylenically unsaturated monomer compound (a) represented by the general formula (1) and a compound (b) having another ethylenically unsaturated monomer double bond. The copolymerization ratio of the monomer compound (a) in the transparent resin or the non-photosensitive transparent resin is 0.1 to 50% by weight based on the total amount of the monomers including (a) and (b). It is preferably occupied, more preferably 10 to 35% by weight. When the copolymerization ratio of the monomer (a) is less than 0.1% by weight, the pigment dispersion effect is lowered. On the other hand, when the amount is more than 50% by weight, the hydrophobicity is increased, and the developability of the black coloring composition may be deteriorated or a residue may be caused.
感光性透明樹脂および非感光性透明樹脂は、着色材100重量部に対して、好ましくは合計して20〜400重量部、より好ましくは合計して50〜250重量部の量で用いることができる。 The photosensitive transparent resin and the non-photosensitive transparent resin can be used in an amount of preferably 20 to 400 parts by weight, more preferably 50 to 250 parts by weight in total, with respect to 100 parts by weight of the colorant. .
本発明の黒色着色組成物においては、感度を高めるために感光性透明樹脂と非感光性透明樹脂を併用するが、十分に感度を高めるためには、感光性透明樹脂の含有量が、感光性透明樹脂と非感光性透明樹脂の合計重量を基準として7〜75重量%を占めることが好ましく、より好ましくは10〜60重量%であり、さらに好ましくは15〜50重量%である。 In the black coloring composition of the present invention, a photosensitive transparent resin and a non-photosensitive transparent resin are used in combination in order to increase sensitivity. However, in order to sufficiently increase sensitivity, the content of the photosensitive transparent resin is photosensitive. It is preferably 7 to 75% by weight based on the total weight of the transparent resin and the non-photosensitive transparent resin, more preferably 10 to 60% by weight, and still more preferably 15 to 50% by weight.
感光性透明樹脂の含有量が7重量%より少ない場合には、黒色着色組成物の感光性が低下し、黒色着色塗膜を形成する場合に十分な硬化性が得られない場合があり、多官能モノマーで硬化性を補っても、黒色着色塗膜の溶剤耐性が十分でない場合がある。また、感光性透明樹脂の含有量が75重量%よりも多い場合には、黒色着色組成物の感度は高くなるが、分散安定性が低下して均一な黒色着色塗膜が得られなくなったり、現像性が低下し、パターニング性が低下したりする場合がある。 When the content of the photosensitive transparent resin is less than 7% by weight, the photosensitivity of the black colored composition is lowered, and sufficient curability may not be obtained when forming a black colored coating film. Even if the curability is supplemented with a functional monomer, the solvent resistance of the black colored coating film may not be sufficient. Further, when the content of the photosensitive transparent resin is more than 75% by weight, the sensitivity of the black colored composition is increased, but the dispersion stability is lowered and a uniform black colored coating film cannot be obtained, In some cases, the developability is lowered and the patterning property is lowered.
4つ以上のエチレン性不飽和二重結合を有する多官能モノマーとしては、ペンタエリスリトールトリ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、エチレンオキサイド変性トリメチロールプロパントリ(メタ)アクリレート、プロピレンオキサイド変性トリメチロールプロパントリ(メタ)アクリレート等の各種アクリル酸エステルおよびメタクリル酸エステル等が代表例に挙げられる。多官能モノマーは、着色組成物の感度アップの観点から、エチレン性不飽和二重結合を4〜12個有することが好ましい。4つ以上のエチレン性不飽和二重結合を有する多官能モノマーは、単独でまたは2種類以上混合して用いることができる。 Polyfunctional monomers having four or more ethylenically unsaturated double bonds include pentaerythritol tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate, ethylene oxide modified trimethylolpropane tri (meth) acrylate, propylene oxide Representative examples include various acrylic esters and methacrylic esters such as modified trimethylolpropane tri (meth) acrylate. It is preferable that a polyfunctional monomer has 4-12 ethylenically unsaturated double bonds from a viewpoint of the sensitivity improvement of a coloring composition. The polyfunctional monomer having four or more ethylenically unsaturated double bonds can be used alone or in admixture of two or more.
4つ以上のエチレン性不飽和二重結合を有する多官能モノマーは、着色材100重量部に対して、好ましくは10〜300重量部、より好ましくは10〜200重量部の量で用いることができる。 The polyfunctional monomer having 4 or more ethylenically unsaturated double bonds can be used in an amount of preferably 10 to 300 parts by weight, more preferably 10 to 200 parts by weight with respect to 100 parts by weight of the colorant. .
4つ以上のエチレン性不飽和二重結合を有する多官能モノマーのエチレン性不飽和二重結合重量モル濃度(感光性樹脂組成物の重量基準)は、感光性透明樹脂のエチレン性不飽和二重結合重量モル濃度(感光性樹脂組成物の重量基準)の好ましくは2.5〜25.0倍、より好ましくは3.5〜20.0倍、さらに好ましくは3.5〜15.0倍である。モノマーのエチレン性不飽和二重結合重量モル濃度の割合が2.5倍より少ない場合には、黒色着色組成物の感度が低下し、黒色着色塗膜を形成する場合に十分な硬化性が得られない。また、25.0倍よりも多い場合には、黒色着色組成物の感度は向上するが、分散安定性の低下や、パターニング性の不良が起こる場合がある。 The ethylenically unsaturated double bond weight molarity (based on the weight of the photosensitive resin composition) of the polyfunctional monomer having four or more ethylenically unsaturated double bonds is the ethylenically unsaturated double bond of the photosensitive transparent resin. Preferably it is 2.5 to 25.0 times, more preferably 3.5 to 20.0 times, still more preferably 3.5 to 15.0 times the bond molarity (based on the weight of the photosensitive resin composition). is there. When the ratio of the ethylenically unsaturated double bond weight molarity of the monomer is less than 2.5 times, the sensitivity of the black colored composition is lowered, and sufficient curability is obtained when forming a black colored coating film. I can't. On the other hand, when it is more than 25.0 times, the sensitivity of the black colored composition is improved, but the dispersion stability may be deteriorated or the patterning property may be deteriorated.
黒色着色材としては、有機または無機の黒色顔料を、単独でまたは2種類以上混合して用いることができる。、例えばカーボンブラック、アニリンブラック、アントラキノン系黒色顔料、ペリレン系黒色顔料、具体的には C.I. Pigment Black 1、6、7、12、20、31等を用いることができる。黒色着色組成物には、赤色顔料、青色顔料、緑色顔料の混合物を用いることもできる。黒色顔料としては、価格、遮光性の大きさからカーボンブラックが好ましく、カーボンブラックは、樹脂などで表面処理されていてもよい。また、色調を調整するため、黒色着色組成物には、青色顔料や紫色顔料を併用することができる。 As the black colorant, organic or inorganic black pigments can be used alone or in admixture of two or more. For example, carbon black, aniline black, anthraquinone black pigment, perylene black pigment, specifically C.I. Pigment Black 1, 6, 7, 12, 20, 31, etc. can be used. A mixture of a red pigment, a blue pigment, and a green pigment can also be used for the black coloring composition. As the black pigment, carbon black is preferable from the viewpoint of price and light shielding properties, and the carbon black may be surface-treated with a resin or the like. Moreover, in order to adjust a color tone, a blue pigment and a purple pigment can be used together in a black coloring composition.
また、カーボンブラックとしては、BET法による比表面積が50〜200m2/gで、フタル酸ジブチルの吸油量が120cc/100g以下で、かつ平均1次粒子径は20〜50nmである物性値を有するものが、分散安定性あるいはパターニング性の点で特に好ましい。 Carbon black has physical properties such that the specific surface area by the BET method is 50 to 200 m 2 / g, the oil absorption of dibutyl phthalate is 120 cc / 100 g or less, and the average primary particle size is 20 to 50 nm. Those are particularly preferable in view of dispersion stability or patterning property.
本発明の黒色着色組成物は、感光性樹脂組成物中に、黒色着色材を三本ロールミル、二本ロールミル、サンドミル、ニーダー、アトライター、ペイントコンディショナー等の各種分散手段を用いて、微細に分散して製造することができる。 The black coloring composition of the present invention finely disperses the black coloring material in the photosensitive resin composition using various dispersing means such as a three roll mill, a two roll mill, a sand mill, a kneader, an attritor, and a paint conditioner. Can be manufactured.
黒色着色材として顔料を用いる場合には、適宜、樹脂型顔料分散剤、色素誘導体、界面活性剤等の分散助剤を用いることができる。分散助剤は、顔料の分散に優れ、分散後の顔料の再凝集を防止する効果が大きいので、分散助剤を用いて顔料を感光性樹脂組成物中に分散してなる黒色着色組成物を用いた場合には、透明性に優れたカラーフィルタが得られる。分散助剤は、黒色着色材100重量部に対して、好ましくは0.1〜40重量部、より好ましくは0.1〜30重量部の量で用いることができる。 When a pigment is used as the black colorant, a dispersion aid such as a resin-type pigment dispersant, a dye derivative, or a surfactant can be appropriately used. Since the dispersion aid is excellent in pigment dispersion and has a great effect of preventing re-aggregation of the pigment after dispersion, a black coloring composition obtained by dispersing the pigment in the photosensitive resin composition using the dispersion aid is used. When used, a color filter excellent in transparency can be obtained. The dispersion aid can be used in an amount of preferably 0.1 to 40 parts by weight, more preferably 0.1 to 30 parts by weight with respect to 100 parts by weight of the black colorant.
樹脂型顔料分散剤は、顔料に吸着する性質を有する顔料親和性部位と、感光性透明樹脂および非感光性透明樹脂と相溶性のある部位とを有し、顔料に吸着して顔料の感光性樹脂組成物への分散を安定化する働きをするものである。樹脂型顔料分散剤としては、ポリウレタン、ポリアクリレートなどのポリカルボン酸エステル、不飽和ポリアミド、ポリカルボン酸、ポリカルボン酸(部分)アミン塩、ポリカルボン酸アンモニウム塩、ポリカルボン酸アルキルアミン塩、ポリシロキサン、長鎖ポリアミノアマイドリン酸塩、水酸基含有ポリカルボン酸エステルや、これらの変性物、ポリ(低級アルキレンイミン)と遊離のカルボキシル基を有するポリエステルとの反応により形成されたアミドやその塩などが用いられる。また、(メタ)アクリル酸−スチレン共重合体、(メタ)アクリル酸−(メタ)アクリル酸エステル共重合体、スチレン−マレイン酸共重合体、ポリビニルアルコール、ポリビニルピロリドンなどの水溶性樹脂や水溶性高分子化合物、ポリエステル系、変性ポリアクリレート、エチレンオキサイド/プロピレンオキサイド付加物等も用いられる。これらは、単独でまたは2種以上を混合して用いることができる。 The resin-type pigment dispersant has a pigment-affinity part that has the property of adsorbing to the pigment and a part that is compatible with the photosensitive transparent resin and the non-photosensitive transparent resin. It functions to stabilize dispersion in the resin composition. Resin-type pigment dispersants include polyurethanes, polycarboxylic acid esters such as polyacrylates, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, polycarboxylic acid alkylamine salts, polycarboxylic acid esters Siloxane, long-chain polyaminoamide phosphate, hydroxyl group-containing polycarboxylic acid ester, modified products thereof, amide formed by reaction of poly (lower alkyleneimine) and polyester having a free carboxyl group, and salts thereof Used. In addition, water-soluble resins such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, and polyvinylpyrrolidone, and water-soluble Polymer compounds, polyesters, modified polyacrylates, ethylene oxide / propylene oxide adducts, and the like are also used. These can be used alone or in admixture of two or more.
市販の樹脂型顔料分散剤としては、ビックケミー社製のDisperbyk−101、103、107、108、110、111、116、130、140、154、161、162、163、164、165、166、170、171、174、180、181、182、183、184、185、190、2000、2001、またはAnti−Terra−U、203、204、またはBYK−P104、P104S、220S、またはLactimon、Lactimon−WSまたはBykumen等、アビシア社製のSOLSPERSE−3000、9000、13240、13650、13940、17000、18000、20000、21000、24000、26000、27000、28000、31845、32000、32500、32600、34750、36600、38500、41000、41090、53095等、エフカケミカルズ社製のEFKA−46、47、48、452、LP4008、4009、LP4010、LP4050、LP4055、400、401、402、403、450、451、453、4540、4550、LP4560、120、150、1501、1502、1503等が挙げられる。 Commercially available resin-type pigment dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170, manufactured by Big Chemie. 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, or Anti-Terra-U, 203, 204, or BYK-P104, P104S, 220S, or Lactimon, Lactimon-WS, or Bykumen SOLSPERSE-3000, 9000, 13240, 13650, 13940, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 320 manufactured by Abyssia 0, 32500, 32600, 34750, 36600, 38500, 41000, 41090, 53095, etc., EFKA-46, 47, 48, 452, LP4008, 4009, LP4010, LP4050, LP4055, 400, 401, 402 manufactured by Efka Chemicals , 403, 450, 451, 453, 4540, 4550, LP4560, 120, 150, 1501, 1502, 1503, and the like.
色素誘導体は、有機色素に置換基を導入した化合物である。有機色素には、一般に色素とは呼ばれていないナフタレン系、アントラキノン系等の淡黄色の芳香族多環化合物も含まれる。色素誘導体としては、特開昭63−305173号公報、特公昭57−15620号公報、特公昭59−40172号公報、特公昭63−17102号公報、特公平5−9469号公報等に記載されているものを使用できる。特に、塩基性基を有する色素誘導体は、顔料の分散効果が大きいため、好適に用いられる。これらは単独でまたは2種類以上を混合して用いることができる。 A pigment derivative is a compound in which a substituent is introduced into an organic pigment. Organic dyes also include light yellow aromatic polycyclic compounds such as naphthalene and anthraquinone that are not generally called dyes. Examples of the dye derivatives are described in JP-A-63-305173, JP-B-57-15620, JP-B-59-40172, JP-B-63-17102, JP-B-5-9469, and the like. You can use what you have. In particular, a pigment derivative having a basic group is preferably used because it has a large pigment dispersion effect. These can be used alone or in admixture of two or more.
色素誘導体が有する塩基性基として具体的には、下記一般式(2)、(3)、(4)および(5)で表される置換基が挙げられる。なかでも、下記一般式(5)で表されるトリアジン骨格を含む塩基性基を有する色素誘導体は、顔料の分散効果が大きいため、好適に用いられる。
式(2):
Specific examples of the basic group possessed by the dye derivative include substituents represented by the following general formulas (2), (3), (4) and (5). Especially, since the pigment | dye derivative which has a basic group containing the triazine skeleton represented by following General formula (5) has a large pigment dispersion effect, it is used suitably.
Formula (2):
nは、1〜10の整数を表し、好ましくは1〜3の整数である。
R4およびR5は、それぞれ独立に、炭素数1〜36の置換されていてもよいアルキル基、炭素数2〜36の置換されていてもよいアルケニル基もしくは置換されていてもよいフェニル基を表すか、またはR4とR5とが結合して更なる窒素、酸素または硫黄原子を含む置換されていてもよい複素環を形成する。R4およびR5は、好ましくは、1〜5個の炭素原子を有する非置換もしくは置換アルキル基である。
R6は、炭素数1〜36の置換されていてもよいアルキル基、炭素数2〜36の置換されていてもよいアルケニル基または置換されていてもよいフェニル基を表す。R6は、好ましくは、1〜4個の炭素原子を有する非置換もしくは置換アルキル基である。
R7、R8、R9およびR10は、それぞれ独立に、水素原子、炭素数1〜36の置換されていてもよいアルキル基、炭素数2〜36の置換されていてもよいアルケニル基または置換されていてもよいフェニル基を表す。R7、R8、R9およびR10は、好ましくは、1〜4個の炭素原子を有する非置換もしくは置換アルキル基である。
Yは、−NR11−Z−NR12−または直接結合を表す。
R11およびR12は、それぞれ独立に、水素原子、炭素数1〜36の置換されていてもよいアルキル基、置換されていてもよい炭素数2〜36のアルケニル基または置換されていてもよいフェニル基を表す。R11およびR12は、好ましくは、それぞれ、水素原子である。
Zは、炭素数1〜36の置換されていてもよいアルキレン基、炭素数2〜36の置換されていてもよいアルケニレン基、または置換されていてもよいフェニレン基を表す。Zは、好ましくは、非置換もしくは置換フェニレン基である。
Pは、下記式(6)で示される置換基または下記式(7)で示される置換基を表す。下記式(6)および(7)において、R4〜R10、およびnは、上に定義したとおりである。
Qは、水酸基、アルコキシル基、下記式(6)で示される置換基または下記式(7)で示される置換基を表す。Qは、好ましくは、下記式(6)で示される置換基である。
式(6):
n represents an integer of 1 to 10, preferably an integer of 1 to 3.
R4 and R5 each independently represents an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group. Or R4 and R5 combine to form an optionally substituted heterocycle containing additional nitrogen, oxygen or sulfur atoms. R4 and R5 are preferably unsubstituted or substituted alkyl groups having 1 to 5 carbon atoms.
R6 represents an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group. R6 is preferably an unsubstituted or substituted alkyl group having 1 to 4 carbon atoms.
R7, R8, R9 and R10 are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms or a substituted group. Represents a good phenyl group. R7, R8, R9 and R10 are preferably unsubstituted or substituted alkyl groups having 1 to 4 carbon atoms.
Y represents -NR11-Z-NR12- or a direct bond.
R11 and R12 each independently represents a hydrogen atom, an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group. Represents. R11 and R12 are preferably each a hydrogen atom.
Z represents an alkylene group having 1 to 36 carbon atoms which may be substituted, an alkenylene group having 2 to 36 carbon atoms which may be substituted, or a phenylene group which may be substituted. Z is preferably an unsubstituted or substituted phenylene group.
P represents a substituent represented by the following formula (6) or a substituent represented by the following formula (7). In the following formulas (6) and (7), R4 to R10 and n are as defined above.
Q represents a hydroxyl group, an alkoxyl group, a substituent represented by the following formula (6) or a substituent represented by the following formula (7). Q is preferably a substituent represented by the following formula (6).
Formula (6):
塩基性基を有する色素誘導体を構成する有機色素としては、例えば、ジケトピロロピロール系色素、アゾ、ジスアゾ、ポリアゾ等のアゾ系色素、フタロシアニン系色素、ジアミノジアントラキノン、アントラピリミジン、フラバントロン、アントアントロン、インダントロン、ピラントロン、ビオラントロン等のアントラキノン系色素、キナクリドン系色素、ジオキサジン系色素、ペリノン系色素、ペリレン系色素、チオインジゴ系色素、イソインドリノン系色素、キノフタロン系色素、スレン系色素、金属錯体系色素が挙げられる。 Examples of the organic dye constituting the dye derivative having a basic group include diketopyrrolopyrrole dyes, azo dyes such as azo, disazo, polyazo, phthalocyanine dyes, diaminodianthraquinone, anthrapyrimidine, flavantrons, Anthraquinone dyes such as anthrone, indanthrone, pyranthrone, violanthrone, quinacridone dyes, dioxazine dyes, perinone dyes, perylene dyes, thioindigo dyes, isoindolinone dyes, quinophthalone dyes, selenium dyes, metal complexes Systematic dyes.
塩基性基を有する色素誘導体は、種々の合成経路で合成することができる。例えば、有機色素に、下記式(8)〜(11)で表される置換基を導入した後、該置換基と反応して一般式(2)〜(5)で表される置換基を形成するアミン成分、例えば、N,N−ジメチルアミノプロピルアミン、N−メチルピペラジン、ジエチルアミンまたは4−[4−ヒドロキシ−6−[3−(ジブチルアミノ)プロピルアミノ]−1,3,5−トリアジン−2−イルアミノ]アニリン等を反応させることによって得られる。
式(8) −SO2Cl
式(9) −COCl
式(10) −CH2NHCOCH2Cl
式(11) −CH2Cl
有機色素がアゾ系色素である場合は、一般式(2)〜(5)で表される置換基をあらかじめジアゾ成分またはカップリング成分に導入し、その後カップリング反応を行うことによって塩基性基を有するアゾ系色素誘導体を製造することもできる。
A pigment derivative having a basic group can be synthesized by various synthetic routes. For example, after introducing a substituent represented by the following formulas (8) to (11) into an organic dye, it reacts with the substituent to form a substituent represented by the general formulas (2) to (5). Amine components such as N, N-dimethylaminopropylamine, N-methylpiperazine, diethylamine or 4- [4-hydroxy-6- [3- (dibutylamino) propylamino] -1,3,5-triazine- It can be obtained by reacting 2-ylamino] aniline or the like.
Equation (8) -SO 2 Cl
Formula (9) -COCl
Equation (10) -CH 2 NHCOCH 2 Cl
Equation (11) -CH 2 Cl
When the organic dye is an azo dye, the basic group is introduced by introducing a substituent represented by the general formulas (2) to (5) into the diazo component or the coupling component in advance and then performing a coupling reaction. It is also possible to produce an azo dye derivative having the same.
また、本発明の塩基性基を有するトリアジン誘導体は、種々の合成経路で合成することができる。例えば、塩化シアヌルを出発原料とし、塩化シアヌルの少なくとも1つの塩素に一般式(2)〜(5)で表される置換基を形成するアミン成分、例えば、N,N−ジメチルアミノプロピルアミンまたはN−メチルピペラジン等を反応させ、次いで塩化シアヌルの残りの塩素と種々のアミンまたはアルコール等を反応させることによって得られる。 The triazine derivative having a basic group of the present invention can be synthesized by various synthetic routes. For example, starting from cyanuric chloride, an amine component that forms a substituent represented by the general formulas (2) to (5) on at least one chlorine of cyanuric chloride, such as N, N-dimethylaminopropylamine or N It is obtained by reacting methylpiperazine or the like and then reacting the remaining chlorine of cyanuric chloride with various amines or alcohols.
一般式(2)〜(5)で表される置換基を形成するために使用されるアミン成分としては、例えば、ジメチルアミン、ジエチルアミン、N,N−エチルイソプロピルアミン、N,N−エチルプロピルアミン、N,N−メチルブチルアミン、N,N−メチルイソブチルアミン、N,N−ブチルエチルアミン、N,N−tert−ブチルエチルアミン、ジイソプロピルアミン、ジプロピルアミン、N,N−sec−ブチルプロピルアミン、ジブチルアミン、ジーsec−ブチルアミン、ジイソブチルアミン、N,N−イソブチル−sec−ブチルアミン、ジアミルアミン、ジイソアミルアミン、ジヘキシルアミン、ジ(2−エチルへキシル)アミン、ジオクチルアミン、N,N−メチルオクタデシルアミン、ジデシルアミン、ジアリルアミン、N,N−エチル−1,2−ジメチルプロピルアミン、N,N−メチルヘキシルアミン、ジオレイルアミン、ジステアリルアミン、N,N−ジメチルアミノメチルアミン、N,N−ジメチルアミノエチルアミン、N,N−ジメチルアミノアミルアミン、N,N−ジメチルアミノブチルアミン、N,N−ジエチルアミノエチルアミン、N,N−ジエチルアミノプロピルアミン、N,N−ジエチルアミノヘキシルアミン、N,N−ジエチルアミノブチルアミン、N,N−ジエチルアミノペンチルアミン、N,N−ジプロピルアミノブチルアミン、N,N−ジブチルアミノプロピルアミン、N,N−ジブチルアミノエチルアミン、N,N−ジブチルアミノブチルアミン、N,N−ジイソブチルアミノペンチルアミン、N,N−メチルーラウリルアミノプロピルアミン、N,N−エチルーヘキシルアミノエチルアミン、N,N−ジステアリルアミノエチルアミン、N,N−ジオレイルアミノエチルアミン、N,N−ジステアリルアミノブチルアミン、ピペリジン、2−ピペコリン、3−ピペコリン、4−ピペコリン、2,4−ルペチジン、2,6−ルペチジン、3,5−ルペチジン、3−ピペリジンメタノール、ピペコリン酸、イソニペコチン酸、イソニコペチン酸メチル、イソニコペチン酸エチル、2−ピペリジンエタノール、ピロリジン、3−ヒドロキシピロリジン、N−アミノエチルピペリジン、N−アミノエチル−4−ピペコリン、N−アミノエチルモルホリン、N−アミノプロピルピペリジン、N−アミノプロピル−2−ピペコリン、N−アミノプロピル−4−ピペコリン、N−アミノプロピルモルホリン、N−メチルピペラジン、N−ブチルピペラジン、N−メチルホモピペラジン、1−シクロペンチルピペラジン、1−アミノ−4−メチルピペラジン、1−シクロペンチルピペラジン等が挙げられる。色素誘導体は、単独または2種類以上を混合して用いることができる。 Examples of the amine component used for forming the substituents represented by the general formulas (2) to (5) include dimethylamine, diethylamine, N, N-ethylisopropylamine, N, N-ethylpropylamine. N, N-methylbutylamine, N, N-methylisobutylamine, N, N-butylethylamine, N, N-tert-butylethylamine, diisopropylamine, dipropylamine, N, N-sec-butylpropylamine, di Butylamine, di-sec-butylamine, diisobutylamine, N, N-isobutyl-sec-butylamine, diamylamine, diisoamylamine, dihexylamine, di (2-ethylhexyl) amine, dioctylamine, N, N-methyloctadecylamine, Didecylamine, diallylamine, N N-ethyl-1,2-dimethylpropylamine, N, N-methylhexylamine, dioleylamine, distearylamine, N, N-dimethylaminomethylamine, N, N-dimethylaminoethylamine, N, N-dimethylamino Amylamine, N, N-dimethylaminobutylamine, N, N-diethylaminoethylamine, N, N-diethylaminopropylamine, N, N-diethylaminohexylamine, N, N-diethylaminobutylamine, N, N-diethylaminopentylamine, N , N-dipropylaminobutylamine, N, N-dibutylaminopropylamine, N, N-dibutylaminoethylamine, N, N-dibutylaminobutylamine, N, N-diisobutylaminopentylamine, N, N-methyl-laurylamino The Pyramine, N, N-ethyl-hexylaminoethylamine, N, N-distearylaminoethylamine, N, N-dioleylaminoethylamine, N, N-distearylaminobutylamine, piperidine, 2-pipecholine, 3-pipecholine, 4 -Pipecoline, 2,4-Lupetidine, 2,6-Lupetidine, 3,5-Lupetidine, 3-Piperidinmethanol, Pipecolic acid, Isonipecotic acid, Methyl isnicopetinate, Ethyl isonicopetic acid, 2-Piperidin ethanol, Pyrrolidine, 3-hydroxy Pyrrolidine, N-aminoethylpiperidine, N-aminoethyl-4-pipecholine, N-aminoethylmorpholine, N-aminopropylpiperidine, N-aminopropyl-2-pipecholine, N-aminopropyl-4-pipecholine, N-amino Examples thereof include propylmorpholine, N-methylpiperazine, N-butylpiperazine, N-methylhomopiperazine, 1-cyclopentylpiperazine, 1-amino-4-methylpiperazine, 1-cyclopentylpiperazine and the like. The pigment derivatives can be used alone or in combination of two or more.
色素誘導体は、顔料重量を100重量部とした時を基準として0.1〜40重量部、好ましくは0.1〜30重量部の量で用いることができる。0.1重量部よりも少ない場合、顔料の分散効果が得られないため好ましくなく、40重量部よりも多い場合、色素誘導体が過剰となり分散性が低下する。 The pigment derivative can be used in an amount of 0.1 to 40 parts by weight, preferably 0.1 to 30 parts by weight, based on 100 parts by weight of the pigment. When the amount is less than 0.1 parts by weight, the effect of dispersing the pigment cannot be obtained, which is not preferable. When the amount is more than 40 parts by weight, the dye derivative becomes excessive and the dispersibility is lowered.
界面活性剤としては、ポリオキシエチレンアルキルエーテル硫酸塩、ドデシルベンゼンスルホン酸ナトリウム、スチレン−アクリル酸共重合体のアルカリ塩、アルキルナフタリンスルホン酸ナトリウム、アルキルジフェニルエーテルジスルホン酸ナトリウム、ラウリル硫酸モノエタノールアミン、ラウリル硫酸トリエタノールアミン、ラウリル硫酸アンモニウム、ステアリン酸モノエタノールアミン、ステアリン酸ナトリウム、ラウリル硫酸ナトリウム、スチレン−アクリル酸共重合体のモノエタノールアミン、ポリオキシエチレンアルキルエーテルリン酸エステルなどのアニオン性界面活性剤;ポリオキシエチレンオレイルエーテル、ポリオキシエチレンラウリルエーテル、ポリオキシエチレンノニルフェニルエーテル、ポリオキシエチレンアルキルエーテルリン酸エステル、ポリオキシエチレンソルビタンモノステアレート、ポリエチレングリコールモノラウレートなどのノニオン性界面活性剤;アルキル4級アンモニウム塩やそれらのエチレンオキサイド付加物などのカオチン性界面活性剤;アルキルジメチルアミノ酢酸ベタインなどのアルキルベタイン、アルキルイミダゾリンなどの両性界面活性剤が挙げられ、これらは単独でまたは2種以上を混合して用いることができる。 Surfactants include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzenesulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkylnaphthalenesulfonate, sodium alkyldiphenyletherdisulfonate, lauryl sulfate monoethanolamine, lauryl Anionic surfactants such as triethanolamine sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate; Polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene Nonionic surfactants such as alkyl ether phosphates, polyoxyethylene sorbitan monostearate, and polyethylene glycol monolaurate; chaotic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts; alkyldimethylamino Examples include amphoteric surfactants such as alkylbetaines such as betaine acetate and alkylimidazolines, and these can be used alone or in admixture of two or more.
本発明の黒色着色組成物には、組成物の経時粘度を安定化させるために貯蔵安定剤を含有させることができる。また、透明基板との密着性を高めるためにシランカップリング剤等の密着向上剤を含有させることもできる。 The black coloring composition of the present invention can contain a storage stabilizer in order to stabilize the viscosity with time of the composition. Moreover, in order to improve adhesiveness with a transparent substrate, adhesion improving agents, such as a silane coupling agent, can also be contained.
また、本発明の黒色着色組成物には、組成物の経時粘度を安定化させるために貯蔵安定剤を含有させることができる。貯蔵安定剤としては、例えばハイドロキノン、メチルハイドロキノン、2,5ジ−tert−ブチルハイドロキノン、tert−ブチルハイドロキノン、tert−ブチル−βベンゾキノン、tert−ブチルハイドロキノン2,5ジフェニル−p−ベンゾキノンなどのハイドロキノン系化合物、ベンジルトリメチルクロライド、ジエチルヒドロキシアミンなどの4級アンモニウムクロライド、乳酸、シュウ酸などの有機酸およびそのメチルエーテル、トリブチルホスフィン、トリオクチルホスフィン、トリシクロヘキシルホスフィン、トリフェニルホスフィン、トリベンジルホスフィンなどのホスフィン化合物、トリオクチルホスフィンオキサイド、トリフェニルホスフィンオキサイドなどのホスフィンオキサイド化合物、トリフェニルホスファイト、トリスノニルフェニルホスファイトなどのホスファイト化合物、t−ブチルピロカテコールなどが挙げられる。貯蔵安定剤は、黒色着色組成物中の着色材100重量部に対して、0.1〜10重量部の量で用いることができる。 The black colored composition of the present invention can contain a storage stabilizer in order to stabilize the viscosity with time of the composition. Examples of storage stabilizers include hydroquinone, such as hydroquinone, methyl hydroquinone, 2,5 di-tert-butyl hydroquinone, tert-butyl hydroquinone, tert-butyl-β benzoquinone, tert-butyl hydroquinone 2,5 diphenyl-p-benzoquinone. Compounds, quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid and their methyl ethers, phosphines such as tributylphosphine, trioctylphosphine, tricyclohexylphosphine, triphenylphosphine and tribenzylphosphine Compounds, phosphine oxide compounds such as trioctylphosphine oxide, triphenylphosphine oxide, triphenylphosphite, trisnonyl Examples thereof include phosphite compounds such as phenyl phosphite and t-butylpyrocatechol. A storage stabilizer can be used in the quantity of 0.1-10 weight part with respect to 100 weight part of coloring materials in a black coloring composition.
シランカップリング剤としては、ビニルトリス(β−メトキシエトキシ)シラン、ビニルエトキシシラン、ビニルトリメトキシシラン等のビニルシラン類、γ−メタクリロキシプロピルトリメトキシシラン等の(メタ)アクリルシラン類、β−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、β−(3,4−エポキシシクロヘキシル)メチルトリメトキシシラン、β−(3,4−エポキシシクロヘキシル)エチルトリエトキシシラン、β−(3,4−エポキシシクロヘキシル)メチルトリエトキシシラン、γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルトリエトキシシラン等のエポキシシラン類、N−β(アミノエチル)γ−アミノプロピルトリメトキシシラン、N−β(アミノエチル)γ−アミノプロピルトリエトキシシラン、N−β(アミノエチル)γ−アミノプロピルメチルジエトキシシシラン、γ−アミノプロピルトリエトキシシラン、γ−アミノプロピルトリメトキシシラン、N−フェニル−γ−アミノプロピルトリメトキシシラン、N−フェニル−γ−アミノプロピルトリエトキシシラン等のアミノシラン類、γ−メルカプトプロピルトリメトキシシラン、γ−メルカプトプロピルトリエトキシシラン等のチオシラン類等が挙げられる。シランカップリング剤は、黒色着色組成物中の着色材100重量部に対して、0.01〜10重量部、好ましくは0.05〜5重量部の量で用いることができる。 Examples of the silane coupling agent include vinyl silanes such as vinyltris (β-methoxyethoxy) silane, vinylethoxysilane, and vinyltrimethoxysilane, (meth) acrylsilanes such as γ-methacryloxypropyltrimethoxysilane, β- (3 , 4-epoxycyclohexyl) ethyltrimethoxysilane, β- (3,4-epoxycyclohexyl) methyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltriethoxysilane, β- (3,4-epoxycyclohexyl) ) Epoxysilanes such as methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β ( Aminoethyl) γ-aminopro Lutriethoxysilane, N-β (aminoethyl) γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, N Examples include aminosilanes such as -phenyl-γ-aminopropyltriethoxysilane, thiosilanes such as γ-mercaptopropyltrimethoxysilane, and γ-mercaptopropyltriethoxysilane. The silane coupling agent can be used in an amount of 0.01 to 10 parts by weight, preferably 0.05 to 5 parts by weight, with respect to 100 parts by weight of the colorant in the black coloring composition.
また、本発明の黒色着色組成物には、黒色着色材を十分に感光性樹脂組成物中に分散させ、ガラス基板等の透明基板上に塗布してブラックマトリックスを形成することを容易にするために、溶剤を含有させることができる。 In addition, in the black coloring composition of the present invention, a black coloring material is sufficiently dispersed in the photosensitive resin composition and applied on a transparent substrate such as a glass substrate to facilitate formation of a black matrix. In addition, a solvent can be contained.
溶剤としては、例えば1,2,3−トリクロロプロパン、1,3−ブタンジオール、1,3-ブチレングリコール、1,3-ブチレングリコールジアセテート、1,4−ジオキサン、2−ヘプタノン、2−メチル−1,3−プロパンジオール、3,5,5-トリメチル-2-シクロヘキセン-1-オン、3,3,5−トリメチルシクロヘキサノン、3−エトキシプロピオン酸エチル、3−メチル−1,3−ブタンジオール、3−メトキシ−3−メチル−1−ブタノール、3−メトキシ−3−メチルブチルアセテート、3-メトキシブタノール、3−メトキシブチルアセテート、4−ヘプタノ
ン、m−キシレン、m−ジエチルベンゼン、m−ジクロロベンゼン、N,N−ジメチルア
セトアミド、N,N−ジメチルホルムアミド、n−ブチルアルコール、n−ブチルベンゼン、n−プロピルアセテート、N−メチルピロリドン、o−キシレン、o−クロロトルエン、o−ジエチルベンゼン、o−ジクロロベンゼン、p−クロロトルエン、p−ジエチルベンゼン、sec−ブチルベンゼン、tert−ブチルベンゼン、γ―ブチロラクトン、イソブチルアルコール、イソホロン、エチレングリコールジエチルエーテル、エチレングリコールジブチルエーテル、エチレングリコールモノイソプロピルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノエチルエーテルアセテート、エチレングリコールモノターシャリーブチルエーテル、エチレングリコールモノブチルエーテル、エチレングリコールモノブチルエーテルアセテート、エチレングリコールモノプロピルエーテル、エチレングリコールモノヘキシルエーテル、エチレングリコールモノメチルエーテル、エチレングリコールモノメチルエーテルアセテート、ジイソブチルケトン、ジエチレングリコールジエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールモノイソプロピルエーテル、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノブチルエーテル、ジエチレングリコールモノブチルエーテルアセテート、ジエチレングリコールモノメチルエーテル、シクロヘキサノール、シクロヘキサノールアセテート、シクロヘキサノン、ジプロピレングリコールジメチルエーテル、ジプロピレングリコールメチルエーテルアセテート、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノブチルエーテル、ジプロピレングリコールモノプロピルエーテル、ジプロピレングリコールモノメチルエーテル、ダイアセトンアルコール、トリアセチン、トリプロピレングリコールモノブチルエーテル、トリプロピレングリコールモノメチルエーテル、プロピレングリコールジアセテート、プロピレングリコールフェニルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノエチルエーテルアセテート、プロピレングリコールモノブチルエーテル、プロピレングリコールモノプロピルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノメチルエーテルプロピオネート、ベンジルアルコール、メチルイソブチルケトン、メチルシクロヘキサノール、酢酸n−アミル、酢酸n−ブチル、酢酸イソアミル、酢酸イソブチル、酢酸プロピル、二塩基酸エステル等が挙げられ、これらを単独でもしくは混合して用いる。
Examples of the solvent include 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, and 2-methyl. -1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl-1,3-butanediol 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene N, N-dimethylacetamide, N, N-dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, N-methylpyrrolidone, o- Xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene Glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol mono Hexyl ether, ethylene glycol monomethyl ether Ter, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone , Dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dip Pyrene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether , Propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methyl cyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, Isobutyl, propyl acetate, include dibasic acid esters such as, used alone or in combination.
溶剤は、着色材100重量部に対して、好ましくは800〜4000重量部、より好ましくは1000〜2500重量部の量で用いることができる。 The solvent can be used in an amount of preferably 800 to 4000 parts by weight, more preferably 1000 to 2500 parts by weight with respect to 100 parts by weight of the colorant.
本発明の黒色着色組成物には、該組成物を紫外線等の光照射により硬化するときには、光重合開始剤等が添加される。
光重合開始剤としては、4−フェノキシジクロロアセトフェノン、4−t−ブチル−ジクロロアセトフェノン、ジエトキシアセトフェノン、1−(4−イソプロピルフェニル)−2−ヒドロキシ−2−メチルプロパン−1−オン、1−ヒドロキシシクロヘキシルフェニルケトン、2−メチル−1[4−(メチルチオ)フェニル]−2−モルフォリノプロパン−1−オン、2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタン−1−オン等のアセトフェノン系光重合開始剤、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル、ベンゾインイソプロピルエーテル、ベンジルジメチルケタール等のベンゾイン系光重合開始剤、ベンゾフェノン、ベンゾイル安息香酸、ベンゾイル安息香酸メチル、4−フェニルベンゾフェノン、ヒドロキシベンゾフェノン、アクリル化ベンゾフェノン、4−ベンゾイル−4’−メチルジフェニルサルファイド等のベンゾフェノン系光重合開始剤、チオキサントン、2−クロロチオキサントン、2−メチルチオキサントン、イソプロピルチオキサントン、2,4−ジイソプロピルチオキサントン等のチオキサントン系光重合開始剤、2,4,6−トリクロロ−s−トリアジン、2−フェニル−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(p−メトキシフェニル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(p−トリル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−ピペロニル−4,6−ビス(トリクロロメチル)−s−トリアジン、2,4−ビス(トリクロロメチル)−6−スチリル−s−トリアジン、2−(ナフト−1−イル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(4−メトキシ−ナフト−1−イル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2,4−トリクロロメチル−(ピペロニル)−6−トリアジン、2,4−トリクロロメチル(4’−メトキシスチリル)−6−トリアジン等のトリアジン系光重合開始剤、ボレート系光重合開始剤、カルバゾール系光重合開始剤、イミダゾール系光重合開始剤等が用いられる。
When the composition is cured by irradiation with light such as ultraviolet rays, a photopolymerization initiator or the like is added to the black colored composition of the present invention.
Examples of the photopolymerization initiator include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- Hydroxycyclohexyl phenyl ketone, 2-methyl-1 [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butane- Acetophenone photopolymerization initiators such as 1-one, benzoin photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzyldimethyl ketal, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4 -F Benzophenone photopolymerization initiators such as nylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone Thioxanthone photopolymerization initiators such as 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4,6-bis (trichloromethyl) -s- Triazine, 2,4-bis (trichloro Til) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxy-naphth-1-yl) -4 , 6-Bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, 2,4-trichloromethyl (4′-methoxystyryl) -6-triazine, etc. A polymerization initiator, a borate photopolymerization initiator, a carbazole photopolymerization initiator, an imidazole photopolymerization initiator, or the like is used.
光重合開始剤は、着色材100重量部に対して、好ましくは1〜200重量部、より好ましくは2〜150重量部の量で用いることができる。 The photopolymerization initiator can be used in an amount of preferably 1 to 200 parts by weight, more preferably 2 to 150 parts by weight with respect to 100 parts by weight of the colorant.
上記光重合開始剤は、単独あるいは2種以上混合して用いるが、増感剤として、α−アシロキシエステル、アシルフォスフィンオキサイド、メチルフェニルグリオキシレート、ベンジル、9,10−フェナンスレンキノン、カンファーキノン、エチルアンスラキノン、4,4’−ジエチルイソフタロフェノン、3,3’,4,4’−テトラ(t−ブチルパーオキシカルボニル)ベンゾフェノン、4,4’−ジエチルアミノベンゾフェノン等の化合物を併用することもできる。 The above photopolymerization initiators are used alone or in combination of two or more. As sensitizers, α-acyloxy ester, acylphosphine oxide, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone. , Camphorquinone, ethylanthraquinone, 4,4′-diethylisophthalophenone, 3,3 ′, 4,4′-tetra (t-butylperoxycarbonyl) benzophenone, 4,4′-diethylaminobenzophenone, etc. It can also be used together.
増感剤は、光重合開始剤100重量部に対して、好ましくは0.1〜60重量部の量で用いることができる。 The sensitizer can be used in an amount of preferably 0.1 to 60 parts by weight with respect to 100 parts by weight of the photopolymerization initiator.
黒色着色材は、黒色着色組成物中(透明樹脂、多官能モノマー、着色材に加え、開始剤や溶剤など、すべての成分を含む着色組成物)に0.5〜20重量%の割合で含有されることが好ましい。また、黒色着色材は、最終的にブラックマトリックス中に好ましくは10〜70重量%、より好ましくは20〜60重量%の割合で含有され、その残部は感光性透明樹脂、非感光性透明樹脂および多官能モノマーから実質的になる。 The black colorant is contained in a ratio of 0.5 to 20% by weight in the black color composition (transparent resin, polyfunctional monomer, color composition including all components such as initiator and solvent). It is preferred that Further, the black colorant is finally contained in the black matrix in a proportion of preferably 10 to 70% by weight, more preferably 20 to 60% by weight, and the remainder is a photosensitive transparent resin, a non-photosensitive transparent resin and It consists essentially of a polyfunctional monomer.
本発明の黒色着色組成物は、遠心分離、焼結フィルタ、メンブレンフィルタ等の手段にて、5μm以上の粗大粒子、好ましくは1μm以上の粗大粒子、さらに好ましくは0.5μm以上の粗大粒子および混入した塵の除去を行うことが好ましい。 The black colored composition of the present invention may be mixed with a coarse particle of 5 μm or more, preferably a coarse particle of 1 μm or more, more preferably a coarse particle of 0.5 μm or more by means of centrifugation, a sintered filter, a membrane filter or the like. It is preferable to remove the dust.
次に、本発明のカラーフィルタについて説明する。
本発明のカラーフィルタは、ガラス板等の透明基板上に、本発明の黒色着色組成物から形成されるブラックマトリックスと、黒以外の少なくとも2色のフィルタセグメントとを備えるものである。フィルタセグメントの色は、青色、緑色、赤色、シアン、エロー、マゼンタ、橙色、紫色などから2〜6色程度選択される。同色系の色で、濃度の違うフィルタセグメントが形成されていてもよい。
Next, the color filter of the present invention will be described.
The color filter of the present invention comprises a black matrix formed of the black coloring composition of the present invention and a filter segment of at least two colors other than black on a transparent substrate such as a glass plate. The color of the filter segment is selected from about 2 to 6 colors from blue, green, red, cyan, yellow, magenta, orange, purple and the like. Filter segments having the same color system and different densities may be formed.
黒色以外の各色着色組成物としては、各色顔料、前記非感光性透明樹脂、前記多官能モノマーを含有する通常の各色着色組成物を用いて形成することができる。 As each color coloring composition other than black, it can be formed using each color pigment, the said non-photosensitive transparent resin, and each normal color coloring composition containing the said polyfunctional monomer.
以下に、各色着色組成物に使用可能な有機顔料の具体例を、カラーインデックス(C.I.)番号で示す。 Below, the specific example of the organic pigment which can be used for each color coloring composition is shown by a color index (C.I.) number.
赤色着色組成物には、C.I. Pigment Red 7、9、14、41、48:1、48:2、48:3、48:4、81:1、81:2、81:3、122、123、146、149、168、177、178、179、184、185、187、192、200、202、208、210、216、220、223、224、226、240、254、255、264、272等の赤色顔料を用いることができる。
また、赤色着色組成物は、前記赤色顔料に加えて、後述する黄色顔料及び/またはオレンジ色顔料も、赤色着色組成物の原料として含むことができる。
Red pigmented compositions include CI Pigment Red 7, 9, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 122, 123, 146, 149, 168, 177, 178, 179, 184, 185, 187, 192, 200, 202, 208, 210, 216, 220, 223, 224, 226, 240, 254, 255, 264, 272, etc. Pigments can be used.
In addition to the red pigment, the red coloring composition can also contain a yellow pigment and / or an orange pigment described later as a raw material of the red coloring composition.
緑色着色組成物には、C.I. Pigment Green 7、10、36、37等の緑色顔料を用いることができ、かつ黄色顔料を併用することができる。 For the green coloring composition, green pigments such as C.I. Pigment Green 7, 10, 36, 37 can be used, and a yellow pigment can be used in combination.
青色着色組成物には、C.I. Pigment Blue 15、15:1、15:2、15:3、15:4、15:6、16、64、80等の青色顔料を用いることができ、かつ紫色顔料を併用することができる。 Blue pigments such as CI Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 64, and 80 can be used for the blue coloring composition, and a purple pigment Can be used in combination.
黄色着色組成物には、C.I. Pigment Yellow 1、2、3、4、5、6、10、12、13、14、15、16、17、18、24、31、32、34、35、35:1、36、36:1、37、37:1、40、42、43、53、55、60、61、62、63、65、73、74、77、81、83、93、94、95、97、98、100、101、104、106、108、109、110、113、114、115、116、117、118、119、120、123、126、127、128、129、138、139、147、150、151、152、153、154、155、156、161、162、164、166、167、168、169、170、171、172、173、174、175、176、177、179、180、181、182、185、187、188、193、194、198、199、213、214等の黄色顔料を用いることができる。
紫色着色組成物には、C.I. Pigment Violet1、19、23、27、29、30、32、37、40、42、50等の顔料を用いることができる。
For the yellow coloring composition, CI Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 1 It can be used yellow pigments such 0,181,182,185,187,188,193,194,198,199,213,214.
In the purple coloring composition, pigments such as CI Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, and 50 can be used.
マゼンタ色着色組成物には、C.I. Pigment Red 7、14、41、48:1、48:2、48:3、48:4、81:1、81:2、81:3、146、177、178、184、185、187、200、202、208、210、246、254、255、264、270、272等の顔料を用いることができ、かつ黄色顔料を併用することができる。
シアン色着色組成物には、C.I. Pigment Blue 15:1、15:2、15:3、15:4、15:6、16、80等の顔料を用いることができる。
For magenta colored compositions, CI Pigment Red 7, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 146, 177, 178 , 184, 185, 187, 200, 202, 208, 210, 246, 254, 255, 264, 270, 272 and the like, and a yellow pigment can be used in combination.
For the cyan coloring composition, pigments such as CI Pigment Blue 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, and 80 can be used.
オレンジ色着色組成物には、C.I.Pigment Orange 36、43、51、55、59、61、71、73等の顔料を用いることができる。 For the orange coloring composition, pigments such as C.I. Pigment Orange 36, 43, 51, 55, 59, 61, 71, 73 can be used.
各色着色組成物には、彩度と明度のバランスをとりつつ良好な塗布性、感度、現像性等を確保するために、無機顔料を含有させることができる。無機顔料としては、酸化チタン、硫酸バリウム、亜鉛華、硫酸鉛、黄色鉛、亜鉛黄、べんがら(赤色酸化鉄(III))、カドミウム赤、群青、紺青、酸化クロム緑、コバルト緑、アンバー、チタンブラック、合成鉄黒、カーボンブラック等が挙げられる。無機顔料は、単独あるいは2種類以上併用して用いられる。無機顔料は顔料重量を100重量部とした時を基準として0.1〜10重量部の量で用いることができる。 Each color coloring composition can contain an inorganic pigment in order to ensure good coatability, sensitivity, developability, etc. while balancing saturation and lightness. Inorganic pigments include titanium oxide, barium sulfate, zinc white, lead sulfate, yellow lead, zinc yellow, red bean (red iron (III) oxide), cadmium red, ultramarine, bitumen, chromium oxide green, cobalt green, amber, titanium Examples thereof include black, synthetic iron black, and carbon black. An inorganic pigment is used individually or in combination of 2 or more types. The inorganic pigment can be used in an amount of 0.1 to 10 parts by weight based on the pigment weight of 100 parts by weight.
また、各色着色組成物には、調色のため、耐熱性を低下させない範囲内で染料を含有させることができる。染料は顔料重量を100重量部とした時を基準として0.1〜10重量部の量で用いることができる。 Moreover, each color coloring composition can contain a dye within the range which does not reduce heat resistance for color matching. The dye can be used in an amount of 0.1 to 10 parts by weight based on the pigment weight being 100 parts by weight.
本発明のカラーフィルタは、フォトリソグラフィー法により、本発明の黒色着色組成物および黒以外の各色着色組成物を用いて基板上にブラックマトリックスおよび各色のフィルタセグメントを形成することにより製造することができる。 The color filter of the present invention can be produced by forming a black matrix and a filter segment of each color on a substrate using the black coloring composition of the present invention and each color coloring composition other than black by a photolithography method. .
透明基板としては、ソーダ石灰ガラス、低アルカリ硼珪酸ガラス、無アルカリアルミノ硼珪酸ガラスなどのガラス板や、ポリカーボネート、ポリメタクリル酸メチル、ポリエチレンテレフタレートなどの樹脂板が用いられる。また、ガラス板や樹脂板の表面には、パネル化後の液晶駆動のために、酸化インジウム、酸化錫などからなる透明電極が形成されていてもよい。 As the transparent substrate, glass plates such as soda lime glass, low alkali borosilicate glass and non-alkali alumino borosilicate glass, and resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate are used. In addition, a transparent electrode made of indium oxide, tin oxide, or the like may be formed on the surface of the glass plate or the resin plate in order to drive the liquid crystal after forming the panel.
ブラックマトリックスおよび各色のフィルタセグメントの乾燥膜厚は、0.2〜10μmであることが好ましく、より好ましくは0.2〜5μmである。塗布膜を乾燥させる際には、減圧乾燥機、コンベクションオーブン、IRオーブン、ホットプレート等を使用してもよい。 The dry film thickness of the black matrix and each color filter segment is preferably 0.2 to 10 μm, more preferably 0.2 to 5 μm. When drying the coating film, a vacuum dryer, a convection oven, an IR oven, a hot plate, or the like may be used.
フォトリソグラフィー法によるブラックマトリックスおよび各色のフィルタセグメントの形成は、下記の方法で行う。すなわち、溶剤現像型あるいはアルカリ現像型着色レジスト材として調製した感光性着色組成物を、透明基板上に、スプレーコートやスピンコート、スリットコート、ロールコート等の塗布方法により、乾燥膜厚が0.2〜10μmとなるように塗布する。必要により乾燥された膜には、この膜と接触あるいは非接触状態で設けられた所定のパターンを有するマスクを通して紫外線露光を行う。その後、溶剤またはアルカリ現像液に浸漬するか、もしくはスプレーなどにより現像液を噴霧して未硬化部を除去し所望のパターンを形成してブラックマトリックスおよび各色のフィルタセグメントを形成することができる。さらに、着色レジスト材の重合を促進するため、必要に応じて加熱を施すこともできる。フォトリソグラフィー法によれば、印刷法より精度の高いブラックマトリックスおよび各色のフィルタセグメントが形成できる。 Formation of the black matrix and the filter segment of each color by photolithography is performed by the following method. That is, the photosensitive coloring composition prepared as a solvent developing type or alkali developing type colored resist material has a dry film thickness of 0. 0 on a transparent substrate by a coating method such as spray coating, spin coating, slit coating or roll coating. It apply | coats so that it may become 2-10 micrometers. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or non-contact with the film. Thereafter, the black matrix and the filter segments of the respective colors can be formed by immersing in a solvent or an alkaline developer, or spraying the developer with a spray or the like to remove the uncured portion to form a desired pattern. Furthermore, in order to accelerate the polymerization of the colored resist material, heating can be performed as necessary. According to the photolithography method, it is possible to form a black matrix and filter segments of each color with higher accuracy than the printing method.
現像に際しては、アルカリ現像液として炭酸ナトリウム、水酸化ナトリウム等の水溶液が使用され、ジメチルベンジルアミン、トリエタノールアミン等の有機アルカリを用いることもできる。また、現像液には、消泡剤や界面活性剤を添加することもできる。 In development, an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Moreover, an antifoamer and surfactant can also be added to a developing solution.
現像処理方法としては、シャワー現像法、スプレー現像法、ディップ(浸漬)現像法、パドル(液盛り)現像法等を適用することができる。 As a development processing method, a shower development method, a spray development method, a dip (immersion) development method, a paddle (liquid accumulation) development method, or the like can be applied.
なお、紫外線露光感度を上げるために、上記着色レジスト材を塗布乾燥後、水溶性あるいはアルカリ可溶性樹脂、例えばポリビニルアルコールや水溶性アクリル樹脂等を塗布乾燥し、酸素による重合阻害を防止する膜を形成した後、紫外線露光を行うこともできる。 In order to increase the UV exposure sensitivity, the colored resist material is applied and dried, and then a water-soluble or alkali-soluble resin such as polyvinyl alcohol or water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Then, ultraviolet exposure can be performed.
また、ブラックマトリックスの乾燥膜厚1μmあたりの光学濃度(OD)は、高遮光性の観点から、3.0以上であることが好ましく、特に好ましくは3.5以上、更に好ましくは3.8以上である。光学濃度は、高いほど好ましいが、着色材自身の光吸収の増加により塗膜露光部の十分な硬化が得られなくなるため、概ね3.0以上4.7以下が望ましい。 Further, the optical density (OD) per 1 μm of the dry thickness of the black matrix is preferably 3.0 or more, particularly preferably 3.5 or more, more preferably 3.8 or more, from the viewpoint of high light shielding properties. It is. The higher the optical density, the better. However, since it is difficult to obtain sufficient curing of the exposed portion of the coating film due to an increase in the light absorption of the colorant itself, it is preferably about 3.0 to 4.7.
以下に、本発明を実施例に基づいて説明するが、本発明はこれによって限定されるものではない。なお、実施例および比較例中、「部」とは「重量部」を意味する。樹脂の分子量は、GPC(ゲルパーミエーションクロマトグラフィ)により測定したポリスチレン換算の重量平均分子量である。
(感光性透明樹脂の合成例1)
反応容器にシクロヘキサノン560部を入れ、容器に窒素ガスを注入しながら80℃に加熱して、同温度でメタクリル酸34.0部、メチルメタクリレート23.0部、n−ブチルメタクリレート、23.0部、単量体(a)としてパラクミルフェノールエチレンオキサイド変性アクリレート(東亜合成株式会社製「アロニックスM110」)22.0部、グリセロールモノメタクリレート47.0部、2,2’−アゾビスイソブチロニトリ
ル4.0部の混合物を1時間かけて滴下して重合反応を行った。滴下終了後、さらに80℃で3時間反応させた後、アゾビスイソブチロニトリル1.0部をシクロヘキサノン55部に溶解させたものを添加し、さらに80℃で1時間反応を続けて、透明樹脂共重合体溶液を得た。
Hereinafter, the present invention will be described based on examples, but the present invention is not limited thereto. In the examples and comparative examples, “parts” means “parts by weight”. The molecular weight of the resin is a weight average molecular weight in terms of polystyrene measured by GPC (gel permeation chromatography).
(Synthesis example 1 of photosensitive transparent resin)
560 parts of cyclohexanone is placed in a reaction vessel, heated to 80 ° C. while injecting nitrogen gas into the vessel, and 34.0 parts of methacrylic acid, 23.0 parts of methyl methacrylate, 23.0 parts of n-butyl methacrylate at the same temperature. , 22.0 parts of paracumylphenol ethylene oxide modified acrylate (“Aronix M110” manufactured by Toagosei Co., Ltd.), 47.0 parts of glycerol monomethacrylate, 2,2′-azobisisobutyronitrile as monomer (a) 4.0 parts of the mixture was added dropwise over 1 hour to carry out the polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C. for 3 hours, and then 1.0 part of azobisisobutyronitrile dissolved in 55 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour. A resin copolymer solution was obtained.
次に、得られた透明樹脂共重合体溶液338部に対して、2−メタクロイルエチルイソシアネート32.0部、ラウリン酸ジブチル錫0.4部、シクロヘキサノン120.0部の混合物を70℃で3時間かけて滴下して感光性透明樹脂溶液を得た。室温まで冷却した後、感光性透明樹脂溶液約2gをサンプリングして180℃、20分加熱乾燥して不揮発分を測定し、先に合成した感光性透明樹脂溶液に不揮発分が20重量%になるようにシクロヘキサノンを添加して感光性樹脂溶液を調製した。得られた感光性透明樹脂1の重量平均分子量Mwは21000、二重結合当量は470であった。 Next, a mixture of 32.0 parts of 2-methacryloylethyl isocyanate, 0.4 parts of dibutyltin laurate, and 120.0 parts of cyclohexanone was added at 3O <0> C to 338 parts of the obtained transparent resin copolymer solution. It dripped over time and the photosensitive transparent resin solution was obtained. After cooling to room temperature, about 2 g of the photosensitive transparent resin solution is sampled and heated and dried at 180 ° C. for 20 minutes to measure the non-volatile content. The previously synthesized photosensitive transparent resin solution has a non-volatile content of 20% by weight. Thus, cyclohexanone was added to prepare a photosensitive resin solution. The obtained photosensitive transparent resin 1 had a weight average molecular weight Mw of 21,000 and a double bond equivalent of 470.
(感光性透明樹脂の合成例2)
反応容器にシクロヘキサノン570部を入れ、容器に窒素ガスを注入しながら80℃に加熱して、同温度でメタクリル酸23.0部、メチルメタクリレート23.0部、ベンジルメタクリレート35.0部、単量体(a)としてパラクミルフェノールエチレンオキサイド変性アクリレート(東亜合成株式会社製「アロニックスM110」)22.0部、グリセロールモノメタクリレート48.0部、2,2’−アゾビスイソブチロニトリル3.0部の混合物を1時間かけて滴下して重合反応を行った。滴下終了後、さらに80℃で3時間反応させた後、アゾビスイソブチロニトリル1.0部をシクロヘキサノン50部に溶解させたものを添加し、さらに80℃で1時間反応を続けて、透明樹脂共重合体溶液を得た。
(Synthesis example 2 of photosensitive transparent resin)
570 parts of cyclohexanone is placed in a reaction vessel and heated to 80 ° C. while injecting nitrogen gas into the vessel. At the same temperature, 23.0 parts of methacrylic acid, 23.0 parts of methyl methacrylate, 35.0 parts of benzyl methacrylate, single amount As the body (a), 22.0 parts of paracumylphenol ethylene oxide modified acrylate (“Aronix M110” manufactured by Toagosei Co., Ltd.), 48.0 parts of glycerol monomethacrylate, 2,2′-azobisisobutyronitrile 3.0 Part of the mixture was added dropwise over 1 hour to carry out the polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C. for 3 hours, then 1.0 part of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour. A resin copolymer solution was obtained.
次に、得られた透明樹脂共重合体溶液336部に対して、2−メタクロイルエチルイソシアネート33.0部、ラウリン酸ジブチル錫0.4部、シクロヘキサノン130.0部の混合物を70℃で3時間かけて滴下して感光性透明樹脂溶液を得た。室温まで冷却した後、感光性透明樹脂溶液約2gをサンプリングして180℃、20分加熱乾燥して不揮発分を測定し、先に合成した感光性透明樹脂溶液に不揮発分が20重量%になるようにシクロヘキサノンを添加して感光性樹脂溶液を調製した。得られた感光性透明樹脂2の重量平均分子量Mwは32000、二重結合当量は460であった。 Next, a mixture of 33.0 parts of 2-methacryloylethyl isocyanate, 0.4 parts of dibutyltin laurate, and 130.0 parts of cyclohexanone was added at 3O <0> C to 336 parts of the obtained transparent resin copolymer solution. It dripped over time and the photosensitive transparent resin solution was obtained. After cooling to room temperature, about 2 g of the photosensitive transparent resin solution is sampled and heated and dried at 180 ° C. for 20 minutes to measure the non-volatile content. The previously synthesized photosensitive transparent resin solution has a non-volatile content of 20% by weight. Thus, cyclohexanone was added to prepare a photosensitive resin solution. The obtained photosensitive transparent resin 2 had a weight average molecular weight Mw of 32000 and a double bond equivalent of 460.
(感光性透明樹脂の合成例3)
反応容器にシクロヘキサノン520部を入れ、容器に窒素ガスを注入しながら80℃に加熱して、同温度でメタクリル酸7.0部、メチルメタクリレート7.0部、2−ヒドロキシエチルメタクリレート63.0部、グリセロールモノメタクリレート66.0部、2,2’−アゾビスイソブチロニトリル4.0部の混合物を1時間かけて滴下して重合反応を行った。滴下終了後、さらに80℃で3時間反応させた後、アゾビスイソブチロニトリル1.0部をシクロヘキサノン70部に溶解させたものを添加し、さらに80℃で1時間反応を続けて、透明樹脂共重合体溶液を得た。
(Synthesis example 3 of photosensitive transparent resin)
520 parts of cyclohexanone is placed in a reaction vessel, heated to 80 ° C. while injecting nitrogen gas into the vessel, and 7.0 parts of methacrylic acid, 7.0 parts of methyl methacrylate, 63.0 parts of 2-hydroxyethyl methacrylate at the same temperature. Then, a mixture of 66.0 parts of glycerol monomethacrylate and 4.0 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour to carry out a polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C. for 3 hours, and then 1.0 part of azobisisobutyronitrile dissolved in 70 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour. A resin copolymer solution was obtained.
次に、得られた透明樹脂共重合体溶液220部に対して、2−メタクロイルエチルイソシアネート56.0部、ラウリン酸ジブチル錫0.4部、シクロヘキサノン220.0部の混合物を70℃で3時間かけて滴下して感光性透明樹脂溶液を得た。室温まで冷却した後、感光性透明樹脂溶液約2gをサンプリングして180℃、20分加熱乾燥して不揮発分を測定し、先に合成した感光性透明樹脂溶液に不揮発分が20重量%になるようにシクロヘキサノンを添加して感光性樹脂溶液を調製した。得られた感光性透明樹脂3の重量平均分子量Mwは20000、二重結合当量は270であった。 Next, with respect to 220 parts of the obtained transparent resin copolymer solution, a mixture of 56.0 parts of 2-methacryloylethyl isocyanate, 0.4 part of dibutyltin laurate, and 220.0 parts of cyclohexanone was added at 70 ° C. at 3 ° C. It dripped over time and the photosensitive transparent resin solution was obtained. After cooling to room temperature, about 2 g of the photosensitive transparent resin solution is sampled and heated and dried at 180 ° C. for 20 minutes to measure the non-volatile content. The previously synthesized photosensitive transparent resin solution has a non-volatile content of 20% by weight. Thus, cyclohexanone was added to prepare a photosensitive resin solution. The obtained photosensitive transparent resin 3 had a weight average molecular weight Mw of 20000 and a double bond equivalent of 270.
(感光性透明樹脂の合成例4)
反応容器にシクロヘキサノン480部を入れ、容器に窒素ガスを注入しながら80℃に加熱して、同温度でメタクリル酸32.0部、メチルメタクリレート24.0部、n−ブチルメタクリレート16.0部、ベンジルメタクリレート29.0部、単量体(a)としてパラクミルフェノールエチレンオキサイド変性アクリレート(東亜合成株式会社製「アロニックスM110」)19.0部、グリセロールモノメタクリレート15.0部、2,2’−アゾビスイソブチロニトリル4.0部の混合物を1時間かけて滴下して重合反応を行った。滴下終了後、さらに80℃で3時間反応させた後、アゾビスイソブチロニトリル1.0部をシクロヘキサノン80部に溶解させたものを添加し、さらに80℃で1時間反応を続けて、透明樹脂共重合体溶液を得た。
(Synthesis example 4 of photosensitive transparent resin)
480 parts of cyclohexanone is placed in a reaction vessel, heated to 80 ° C. while injecting nitrogen gas into the vessel, and at the same temperature, 32.0 parts of methacrylic acid, 24.0 parts of methyl methacrylate, 16.0 parts of n-butyl methacrylate, 29.0 parts of benzyl methacrylate, 19.0 parts of paracumylphenol ethylene oxide modified acrylate (“Aronix M110” manufactured by Toagosei Co., Ltd.) as monomer (a), 15.0 parts of glycerol monomethacrylate, 2,2′- A mixture of 4.0 parts of azobisisobutyronitrile was added dropwise over 1 hour to conduct a polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C. for 3 hours, and then 1.0 part of azobisisobutyronitrile dissolved in 80 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour. A resin copolymer solution was obtained.
次に、得られた透明樹脂共重合体溶液445部に対して、2−メタクロイルエチルイソシアネート14.0部、ラウリン酸ジブチル錫0.4部、シクロヘキサノン55.0部の混合物を70℃で3時間かけて滴下して感光性透明樹脂溶液を得た。室温まで冷却した後、感光性透明樹脂溶液約2gをサンプリングして180℃、20分加熱乾燥して不揮発分を測定し、先に合成した感光性透明樹脂溶液に不揮発分が20重量%になるようにシクロヘキサノンを添加して感光性樹脂溶液を調製した。得られた感光性透明樹脂4の重量平均分子量Mwは21000、二重結合当量は1000であった。 Next, with respect to 445 parts of the obtained transparent resin copolymer solution, a mixture of 14.0 parts of 2-methacryloylethyl isocyanate, 0.4 part of dibutyltin laurate and 55.0 parts of cyclohexanone was added at 70 ° C. It dripped over time and the photosensitive transparent resin solution was obtained. After cooling to room temperature, about 2 g of the photosensitive transparent resin solution is sampled and heated and dried at 180 ° C. for 20 minutes to measure the non-volatile content. The previously synthesized photosensitive transparent resin solution has a non-volatile content of 20% by weight. Thus, cyclohexanone was added to prepare a photosensitive resin solution. The obtained photosensitive transparent resin 4 had a weight average molecular weight Mw of 21000 and a double bond equivalent of 1000.
(感光性透明樹脂の合成例5)
反応容器にシクロヘキサノン560部を入れ、容器に窒素ガスを注入しながら80℃に加熱して、同温度でメタクリル酸22.0部、n−ブチルメタクリレート22.0部、2−ヒドロキシエチルメタクリレート104.0部、2,2’−アゾビスイソブチロニトリル4.0部の混合物を1時間かけて滴下して重合反応を行った。滴下終了後、さらに80℃で3時間反応させた後、アゾビスイソブチロニトリル1.0部をシクロヘキサノン50部に溶解させたものを添加し、さらに80℃で1時間反応を続けて、透明樹脂共重合体溶液を得た。
(Synthesis example 5 of photosensitive transparent resin)
560 parts of cyclohexanone was put in a reaction vessel, heated to 80 ° C. while injecting nitrogen gas into the vessel, and at the same temperature, 22.0 parts of methacrylic acid, 22.0 parts of n-butyl methacrylate, 2-hydroxyethyl methacrylate 104. A polymerization reaction was carried out by dropping a mixture of 0 part and 4.0 part of 2,2′-azobisisobutyronitrile over 1 hour. After completion of the dropwise addition, the mixture was further reacted at 80 ° C. for 3 hours, then 1.0 part of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour. A resin copolymer solution was obtained.
次に、得られた透明樹脂共重合体溶液338部に対して、2−メタクロイルエチルイソシアネート33.0部、ラウリン酸ジブチル錫0.4部、シクロヘキサノン130.0部の混合物を70℃で3時間かけて滴下して感光性透明樹脂溶液を得た。室温まで冷却した後、感光性透明樹脂溶液約2gをサンプリングして180℃、20分加熱乾燥して不揮発分を測定し、先に合成した感光性透明樹脂溶液に不揮発分が20重量%になるようにシクロヘキサノンを添加して感光性樹脂溶液を調製した。得られた感光性透明樹脂5の重量平均分子量Mwは20000、二重結合当量は470であった。 Next, a mixture of 33.0 parts of 2-methacryloylethyl isocyanate, 0.4 parts of dibutyltin laurate, and 130.0 parts of cyclohexanone was added at 3O <0> C to 338 parts of the obtained transparent resin copolymer solution. It dripped over time and the photosensitive transparent resin solution was obtained. After cooling to room temperature, about 2 g of the photosensitive transparent resin solution is sampled and heated and dried at 180 ° C. for 20 minutes to measure the non-volatile content. The previously synthesized photosensitive transparent resin solution has a non-volatile content of 20% by weight. Thus, cyclohexanone was added to prepare a photosensitive resin solution. The obtained photosensitive transparent resin 5 had a weight average molecular weight Mw of 20000 and a double bond equivalent of 470.
(感光性透明樹脂の合成例6)
反応容器にシクロヘキサノン570部を入れ、容器に窒素ガスを注入しながら80℃に加熱して、同温度でメタクリル酸7.0部、メチルメタクリレート11.0部、ベンジルメタクリレート32.0部、2−ヒドロキシエチルメタクリレート101.0部、2,2’−アゾビスイソブチロニトリル3.0部の混合物を1時間かけて滴下して重合反応を行った。滴下終了後、さらに80℃で3時間反応させた後、アゾビスイソブチロニトリル1.0部をシクロヘキサノン50部に溶解させたものを添加し、さらに80℃で1時間反応を続けて、透明樹脂共重合体溶液を得た。
(Synthesis example 6 of photosensitive transparent resin)
570 parts of cyclohexanone was placed in a reaction vessel and heated to 80 ° C. while injecting nitrogen gas into the vessel. At the same temperature, 7.0 parts of methacrylic acid, 11.0 parts of methyl methacrylate, 32.0 parts of benzyl methacrylate, 2- A mixture of 101.0 parts of hydroxyethyl methacrylate and 3.0 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour to carry out a polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C. for 3 hours, then 1.0 part of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour. A resin copolymer solution was obtained.
次に、得られた透明樹脂共重合体溶液337部に対して、2−メタクロイルエチルイソシアネート33.0部、ラウリン酸ジブチル錫0.4部、シクロヘキサノン130.0部の混合物を70℃で3時間かけて滴下して感光性透明樹脂溶液を得た。室温まで冷却した後、感光性透明樹脂溶液約2gをサンプリングして180℃、20分加熱乾燥して不揮発分を測定し、先に合成した感光性透明樹脂溶液に不揮発分が20重量%になるようにシクロヘキサノンを添加して感光性樹脂溶液を調製した。得られた感光性透明樹脂6の重量平均分子量Mwは30000、二重結合当量は460であった。 Next, with respect to 337 parts of the obtained transparent resin copolymer solution, 33.0 parts of 2-methacryloyl ethyl isocyanate, 0.4 part of dibutyltin laurate, and 130.0 parts of cyclohexanone were mixed at 70 ° C. at 3 ° C. It dripped over time and the photosensitive transparent resin solution was obtained. After cooling to room temperature, about 2 g of the photosensitive transparent resin solution is sampled and heated and dried at 180 ° C. for 20 minutes to measure the non-volatile content. The previously synthesized photosensitive transparent resin solution has a non-volatile content of 20% by weight. Thus, cyclohexanone was added to prepare a photosensitive resin solution. The obtained photosensitive transparent resin 6 had a weight average molecular weight Mw of 30,000 and a double bond equivalent of 460.
(非感光性透明樹脂の合成例1)
反応容器にシクロヘキサノン370部を入れ、容器に窒素ガスを注入しながら80℃に加熱して、同温度でメタクリル酸20.0部、メチルメタクリレート10.0部、n−ブチルメタクリレート55.0部、2−ヒドロキシエチルメタクリレート15.0部、2,2’−アゾビスイソブチロニトリル4.0部の混合物を1時間かけて滴下して重合反応を行った。滴下終了後、さらに80℃で3時間反応させた後、アゾビスイソブチロニトリル1.0部をシクロヘキサノン50部に溶解させたものを添加し、さらに80℃で1時間反応を続けて、非感光性透明樹脂共重合体溶液を得た。
(Synthesis example 1 of non-photosensitive transparent resin)
370 parts of cyclohexanone was put in a reaction vessel, heated to 80 ° C. while injecting nitrogen gas into the vessel, 20.0 parts of methacrylic acid, 10.0 parts of methyl methacrylate, 55.0 parts of n-butyl methacrylate at the same temperature, A mixture of 15.0 parts of 2-hydroxyethyl methacrylate and 4.0 parts of 2,2′-azobisisobutyronitrile was added dropwise over 1 hour to carry out a polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C. for 3 hours, then 1.0 part of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour. A photosensitive transparent resin copolymer solution was obtained.
室温まで冷却した後、非感光性透明樹脂溶液約2gをサンプリングして180℃、20分加熱乾燥して不揮発分を測定し、先に合成した非感光性透明樹脂溶液に不揮発分が20重量%になるようにシクロヘキサノンを添加して非感光性樹脂溶液を調製した。得られた非感光性透明樹脂1の重量平均分子量Mwは40000であった。 After cooling to room temperature, about 2 g of the non-photosensitive transparent resin solution was sampled and heated and dried at 180 ° C. for 20 minutes to measure the non-volatile content. The non-photosensitive transparent resin solution synthesized earlier had a non-volatile content of 20% by weight. Cyclohexanone was added so that a non-photosensitive resin solution was prepared. The obtained non-photosensitive transparent resin 1 had a weight average molecular weight Mw of 40000.
(非感光性透明樹脂の合成例2)
反応容器にシクロヘキサノン70部を入れ、容器に窒素ガスを注入しながら80℃に加熱して、同温度でn−ブチルメタクリレート12.3部、2−ヒドロキシエチルメタクリレート4.6部、メタクリル酸5.3部、単量体(a)としてパラクミルフェノールエチレンオキサイド変性アクリレート(東亜合成株式会社製「アロニックスM110」)7.4部、2,2’−アゾビスイソブチロニトリル0.4部の混合物を2時間かけて滴下して重合反応を行った。滴下終了後、さらに80℃で3時間反応させた後、アゾビスイソブチロニトリル0.2部をシクロヘキサノン10部に溶解させたものを添加し、さらに80℃で1時間反応を続けて、非感光性透明樹脂共重合体溶液を得た。
(Synthesis example 2 of non-photosensitive transparent resin)
70 parts of cyclohexanone is placed in a reaction vessel, heated to 80 ° C. while injecting nitrogen gas into the vessel, and 12.3 parts of n-butyl methacrylate, 4.6 parts of 2-hydroxyethyl methacrylate, and 5.5 methacrylic acid at the same temperature. 3 parts, 7.4 parts of paracumylphenol ethylene oxide modified acrylate ("Aronix M110" manufactured by Toa Gosei Co., Ltd.) as monomer (a), 0.4 part of 2,2'-azobisisobutyronitrile Was added dropwise over 2 hours to carry out the polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C. for 3 hours, then 0.2 parts of azobisisobutyronitrile dissolved in 10 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour. A photosensitive transparent resin copolymer solution was obtained.
室温まで冷却した後、非感光性透明樹脂溶液約2gをサンプリングして180℃、20分加熱乾燥して不揮発分を測定し、先に合成した非感光性透明樹脂溶液に不揮発分が20重量%になるようにシクロヘキサノンを添加して非感光性樹脂溶液を調製した。得られた非感光性透明樹脂2の重量平均分子量Mwは27000であった。 After cooling to room temperature, about 2 g of the non-photosensitive transparent resin solution was sampled and heated and dried at 180 ° C. for 20 minutes to measure the non-volatile content. The non-photosensitive transparent resin solution synthesized earlier had a non-volatile content of 20% by weight. Cyclohexanone was added so that a non-photosensitive resin solution was prepared. The obtained non-photosensitive transparent resin 2 had a weight average molecular weight Mw of 27000.
(非感光性透明樹脂の合成例3)
反応容器にシクロヘキサノン70部を入れ、容器に窒素ガスを注入しながら80℃に加熱して、同温度でn−ブチルメタクリレート14.4部、2−ヒドロキシエチルメタクリレート4.6部、メタクリル酸3.2部、単量体(a)としてパラクミルフェノールエチレンオキサイド変性アクリレート(東亜合成株式会社製「アロニックスM110」)7.4部、2,2’−アゾビスイソブチロニトリル0.4部の混合物を2時間かけて滴下して重合反応を行った。滴下終了後、さらに80℃で3時間反応させた後、アゾビスイソブチロニトリル0.2部をシクロヘキサノン10部に溶解させたものを添加し、さらに80℃で1時間反応を続けて、非感光性透明樹脂共重合体溶液を得た。
(Synthesis example 3 of non-photosensitive transparent resin)
70 parts of cyclohexanone is put in a reaction vessel, heated to 80 ° C. while injecting nitrogen gas into the vessel, and at the same temperature, 14.4 parts of n-butyl methacrylate, 4.6 parts of 2-hydroxyethyl methacrylate, 3. 2 parts, a mixture of 7.4 parts paracumylphenol ethylene oxide modified acrylate ("Aronix M110" manufactured by Toa Gosei Co., Ltd.) as monomer (a), 0.4 parts 2,2'-azobisisobutyronitrile Was added dropwise over 2 hours to carry out the polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C. for 3 hours, then 0.2 parts of azobisisobutyronitrile dissolved in 10 parts of cyclohexanone was added, and the reaction was further continued at 80 ° C. for 1 hour. A photosensitive transparent resin copolymer solution was obtained.
室温まで冷却した後、非感光性透明樹脂溶液約2gをサンプリングして180℃、20分加熱乾燥して不揮発分を測定し、先に合成した非感光性透明樹脂溶液に不揮発分が20重量%になるようにシクロヘキサノンを添加して非感光性樹脂溶液を調製した。得られた非感光性透明樹脂3の重量平均分子量Mwは25000であった。 After cooling to room temperature, about 2 g of the non-photosensitive transparent resin solution was sampled and heated and dried at 180 ° C. for 20 minutes to measure the non-volatile content. The non-photosensitive transparent resin solution synthesized earlier had a non-volatile content of 20% by weight. Cyclohexanone was added so that a non-photosensitive resin solution was prepared. The obtained non-photosensitive transparent resin 3 had a weight average molecular weight Mw of 25,000.
感光性透明樹脂の合成例1〜6で得られた感光性透明樹脂1〜6、および非感光性透明樹脂の合成例1〜3で得られた非感光性透明樹脂1〜3の重量平均分子量Mw、二重結合当量および酸価を表1に示す。なお、酸価はJIS−K−0070に準拠して測定、算出した。 Photosensitive transparent resins 1 to 6 obtained in Synthesis Examples 1 to 6 of the photosensitive transparent resin, and non-photosensitive transparent resins 1 to 3 obtained in Synthesis Examples 1 to 3 of the non-photosensitive transparent resin Mw, double bond equivalent and acid value are shown in Table 1. The acid value was measured and calculated according to JIS-K-0070.
[実施例1]
(顔料分散体の製造方法)
下記の組成の混合物を均一に撹拌混合した後、直径1mmのジルコニアビーズを用いて、アイガーミル(アイガージャパン社製「ミニモデルM−250 MKII」)で2時間分散した後、5μmのフィルタで濾過し、顔料分散体を作製した。
黒色顔料:カーボンブラック 16.0部
(三菱化学社製「MA11」)
トリアジン系色素誘導体(下記式(12)) 0.8部
式(12):
[Example 1]
(Method for producing pigment dispersion)
After the mixture having the following composition is uniformly stirred and mixed, the mixture is dispersed for 2 hours with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) using zirconia beads having a diameter of 1 mm, and then filtered through a 5 μm filter. A pigment dispersion was prepared.
Black pigment: 16.0 parts of carbon black (“MA11” manufactured by Mitsubishi Chemical Corporation)
Triazine dye derivative (formula (12) below) 0.8 part formula (12):
非感光性透明樹脂1溶液 12.0部
シクロヘキサノン 67.2部
(黒色着色組成物の製造方法)
ついで、下記組成の混合物を均一になるように攪拌混合した後、1μmのフィルタで濾過して、感光性を有する黒色着色組成物を得た。
実施例1で調整した顔料分散体 62.0部
感光性透明樹脂1溶液 5.7部
非感光性透明樹脂1溶液 14.3部
ジペンタエリスリトールヘキサアクリレート 2.2部
光重合開始剤(チバスペシャルティケミカルズ社製「イルガキュアOXE02」) 0.8部
シクロヘキサノン 15.0部
(Method for producing black colored composition)
Next, the mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1 μm filter to obtain a black colored composition having photosensitivity.
Pigment dispersion prepared in Example 1 62.0 parts Photosensitive transparent resin 1 solution 5.7 parts Non-photosensitive transparent resin 1 solution 14.3 parts Dipentaerythritol hexaacrylate 2.2 parts Photopolymerization initiator (Ciba Specialty) Chemicals "Irgacure OXE02") 0.8 parts Cyclohexanone 15.0 parts
[実施例2〜26および比較例1〜5]
表3に示す感光性の透明樹脂溶液、非感光性の透明樹脂溶液、および多官能モノマーを表3に示す割合(固形分の重量比)となるように配合し、実施例1と同様にして感光性を有する黒色着色組成物(黒色レジスト材)を得た。感光性透明樹脂及び非感光性透明樹脂については、多官能モノマーとともに表3に示す割合となるよう、感光性透明樹脂溶液、非感光性透明樹脂溶液を調整した。得られた黒色着色組成物100重量部中に占めるこれら3成分を合わせた割合は、実施例1〜26及び比較例1〜5について全て同じである。実施例及び比較例で感光性透明樹脂、非感光性透明樹脂の合成結果を表1に、使用した多官能モノマーの一覧を表2に示す。
[Examples 2 to 26 and Comparative Examples 1 to 5]
The photosensitive transparent resin solution shown in Table 3, the non-photosensitive transparent resin solution, and the polyfunctional monomer were blended so as to have the ratio shown in Table 3 (weight ratio of the solid content). A black colored composition (black resist material) having photosensitivity was obtained. About the photosensitive transparent resin and the non-photosensitive transparent resin, the photosensitive transparent resin solution and the non-photosensitive transparent resin solution were adjusted so that it might become the ratio shown in Table 3 with a polyfunctional monomer. The ratio of these three components in 100 parts by weight of the obtained black colored composition is the same for Examples 1 to 26 and Comparative Examples 1 to 5. Table 1 shows the synthesis results of the photosensitive transparent resin and the non-photosensitive transparent resin in Examples and Comparative Examples, and Table 2 shows a list of the polyfunctional monomers used.
そして表3には、感光性透明樹脂及び非感光性透明樹脂の合計重量を基準とした全ての樹脂に対する感光性透明樹脂の含有量(重量%)割合を算出した結果を示した。 Table 3 shows the results of calculating the content (% by weight) of the photosensitive transparent resin with respect to all the resins based on the total weight of the photosensitive transparent resin and the non-photosensitive transparent resin.
また表3には、黒色着色組成物に含まれる感光性透明樹脂、非感光性透明樹脂、および多官能モノマーの合計重量を基準として、該多官能モノマーに含まれるエチレン性不飽和二重結合重量モル濃度(Cb)の、該感光性透明樹脂に含まれるエチレン性不飽和二重結合重量モル濃度(Ca)に対する割合(Cb/Ca)を算出した結果を示した。 Table 3 also shows the weight of ethylenically unsaturated double bonds contained in the polyfunctional monomer based on the total weight of the photosensitive transparent resin, non-photosensitive transparent resin, and polyfunctional monomer contained in the black coloring composition. The result of calculating the ratio (Cb / Ca) of the molar concentration (Cb) to the ethylenically unsaturated double bond weight molar concentration (Ca) contained in the photosensitive transparent resin is shown.
さらに表3には、黒色着色樹脂組成物に含まれる感光性透明樹脂の酸価と、非感光性透明樹脂の酸価との差(ΔA)を示した。 Further, Table 3 shows the difference (ΔA) between the acid value of the photosensitive transparent resin contained in the black colored resin composition and the acid value of the non-photosensitive transparent resin.
さらに加えて表3には、黒色着色樹脂組成物に含まれる感光性透明樹脂、非感光性透明樹脂、および多官能モノマーの合計重量を基準として、該黒色着色組成物中のエチレン性不飽和二重結合の重量モル濃度(官能基の密度)(mol/g)を算出した結果を示した。 In addition, Table 3 shows, based on the total weight of the photosensitive transparent resin, the non-photosensitive transparent resin, and the polyfunctional monomer contained in the black colored resin composition, the ethylenically unsaturated diene in the black colored composition. The results of calculating the weight molar concentration (density of functional groups) (mol / g) of the heavy bond are shown.
実施例及び比較例で得られた黒色着色組成物について、下記の方法で粘度安定性、感度、パターニング性、光学濃度(OD)及び耐溶剤性を評価した。
[粘度安定性評価]
黒色着色組成物を調製した翌日の初期粘度と、40℃で1週間、経時促進させた経時粘度をE型粘度計(東機産業社製「ELD型粘度計」)を用いて、25℃において回転数20rpmという条件で測定した。この初期粘度から経時粘度への変化率を下記数式(III)を用いて算出した結果を表4に示す。
下記数式(III):
[レジスト経時粘度変化率]=|([初期粘度]−[経時粘度])/[初期粘度]×100|
About the black coloring composition obtained by the Example and the comparative example, viscosity stability, sensitivity, patterning property, optical density (OD), and solvent resistance were evaluated by the following method.
[Viscosity stability evaluation]
Using an E-type viscometer (“ELD viscometer” manufactured by Toki Sangyo Co., Ltd.) at 25 ° C., the initial viscosity of the next day after the black colored composition was prepared and the time-lapse viscosity accelerated at 40 ° C. for 1 week. The measurement was performed under the condition of a rotation speed of 20 rpm. Table 4 shows the results of calculating the rate of change from the initial viscosity to the time-dependent viscosity using the following mathematical formula (III).
Formula (III) below:
[Change rate of resist viscosity with time] = | ([initial viscosity] − [viscosity with time]) / [initial viscosity] × 100 |
[感度]
黒色着色組成物をスピンコート法により10cm×10cmのガラス基板に塗工した後、クリーンオーブン中で70℃で15分の乾燥により乾燥膜厚約1μmの塗膜を作製
し、膜厚を測定した。その後、超高圧水銀ランプを用い、18μmのストライプ状のブラックマトリックスパターンを備えたフォトマスクを介して各種露光量(mJ/cm2)の紫外線を露光した。炭酸ナトリウム水溶液を用いてスプレー現像した後、イオン交換水で洗浄することで未露光部分を取り除き、ストライプ状のブラックマトリックスパターンを形成した。現像・水洗後の露光部分の膜厚を測定し、現像前の膜厚に対し95%以上の膜厚が得られる最小露光量(mJ/cm2)を感度とした。評価のランクは次の通りであり、結果を表4に示す。
○:50mJ/cm2未満
△:50mJ/cm2以上200mJ/cm2未満
×:200mJ/cm2以上
[sensitivity]
After coating the black coloring composition on a 10 cm × 10 cm glass substrate by a spin coating method, a coating film having a dry film thickness of about 1 μm was prepared by drying at 70 ° C. for 15 minutes in a clean oven, and the film thickness was measured. . Thereafter, using an ultrahigh pressure mercury lamp, various exposure amounts (mJ / cm 2 ) of ultraviolet rays were exposed through a photomask provided with a 18 μm striped black matrix pattern. After spray development using an aqueous sodium carbonate solution, the unexposed portion was removed by washing with ion exchange water to form a striped black matrix pattern. The film thickness of the exposed part after development and washing was measured, and the minimum exposure amount (mJ / cm 2 ) at which a film thickness of 95% or more with respect to the film thickness before development was obtained was taken as the sensitivity. The rank of evaluation is as follows, and the results are shown in Table 4.
○: Less than 50 mJ / cm 2 Δ: 50 mJ / cm 2 or more and less than 200 mJ / cm 2 ×: 200 mJ / cm 2 or more
[パターニング性]
パターニング性評価は、[感度]評価と同様の方法においてガラス基板に塗工・乾燥し、露光量100mJ/cm2でストライプ状のブラックマトリックスパターンを形成し、次いでクリーンオーブン中で230℃で60分間加熱処理をして得られたパターンの形状を、(1)パタ−ンの直線性、(2)パタ−ンの断面形状により評価を行った。結果を表4に示す。
[Patternability]
In the patterning evaluation, a glass substrate was coated and dried in the same manner as the [sensitivity] evaluation to form a striped black matrix pattern with an exposure amount of 100 mJ / cm 2 , and then in a clean oven at 230 ° C. for 60 minutes. The shape of the pattern obtained by the heat treatment was evaluated by (1) the linearity of the pattern and (2) the cross-sectional shape of the pattern. The results are shown in Table 4.
(1)については、光学顕微鏡により観察して評価を行った。評価のランクは次の通りである。
○:直線性良好(直線部分に欠けが見られない場合)
△:部分的に直線性良好(直線部分の一部に欠けが見られる場合)
×:直線性不良(直線部分の全体にわたって欠けが多数見られる場合)
(2)については、走査型電子顕微鏡(SEM)により観察して評価を行った。評価のランクは次の通りである。
○:順テーパー形状。
△:ノンテーパー形状。
×:逆テーパー形状。
(1) was evaluated by observing with an optical microscope. The rank of evaluation is as follows.
○: Good linearity (when there is no chipping in the straight line part)
Δ: Partially good linearity (when a part of the straight line is chipped)
X: Poor linearity (when a lot of chips are seen over the entire straight line)
(2) was evaluated by observing with a scanning electron microscope (SEM). The rank of evaluation is as follows.
○: Forward tapered shape.
Δ: Non-tapered shape.
X: Reverse taper shape.
[光学濃度(OD)]
黒色着色組成物を、マスクを介さず露光量100mJ/cm2で全面露光した以外は、[パターニング性]評価と同様の方法において黒色着色組成物塗工基板を作製し、膜厚を測定した。このようにして得られた黒色着色組成物塗工基板の光学濃度(OD)を、マクベス濃度計(GRETAG D200−II)により測定し、測定光学濃度(OD)を測定膜厚で除し、単位膜厚当たりの光学濃度OD(/μm)を求めた。結果を表4に示す。
[Optical density (OD)]
A black colored composition-coated substrate was prepared in the same manner as in [Patternability] evaluation, except that the entire surface of the black colored composition was exposed at an exposure amount of 100 mJ / cm 2 without using a mask, and the film thickness was measured. The optical density (OD) of the black colored composition coated substrate thus obtained was measured with a Macbeth densitometer (GRETAG D200-II), the measured optical density (OD) was divided by the measured film thickness, and the unit The optical density OD (/ μm) per film thickness was determined. The results are shown in Table 4.
[耐溶剤性]
光学濃度(OD)測定用に作製した基板の一部をN−メチルピロリドン(NMP)に30分間浸漬後、浸漬した部分の単位膜厚当たりの光学濃度(OD/μm)を測定し、浸漬前のODと浸漬後のODの差(ΔOD)を算出した。評価のランクは次の通りであり、結果を表4に示す。
○:ΔOD=0.1未満
△:ΔOD=0.1以上0.2未満
×:ΔOD=0.2以上
[Solvent resistance]
After immersing a part of the substrate prepared for optical density (OD) measurement in N-methylpyrrolidone (NMP) for 30 minutes, the optical density (OD / μm) per unit film thickness of the immersed part is measured and before immersion. The difference (ΔOD) between the OD and the OD after immersion was calculated. The rank of evaluation is as follows, and the results are shown in Table 4.
○: ΔOD = less than 0.1 Δ: ΔOD = 0.1 or more and less than 0.2 ×: ΔOD = 0.2 or more
表4に示すように、感光性透明樹脂、非感光性透明樹脂、4つ以上のエチレン性不飽和二重結合を有する多官能モノマーの各成分の配合比が適性でない場合、特に官能基密度が適正な範囲にない場合には、黒色着色組成物としての感度が不十分であったり、パターニング性が不良であったりする。一方、黒色着色組成物中の各成分の配合比が適性である場合には、高感度化と良好なパターニング性を両立することができている。黒色着色組成物の分散安定性とパターニング性は、黒色着色組成物中に配合する感光性透明樹脂および非感光性透明樹脂の特性や比率にも大きく影響され、実施例18、19、21、24〜26などでは分散性に優れた感光性透明樹脂および非感光性透明樹脂を用い、適正量の感光性透明樹脂をバランス良く配合することで、分散安定性と良好なパターニング性を両立している。また、黒色着色組成物中に感光性透明樹脂を適正量で配合することにより、これまでにない耐溶剤性に優れた黒色塗膜を得ることができた。 As shown in Table 4, when the blending ratio of each component of a photosensitive transparent resin, a non-photosensitive transparent resin, and a polyfunctional monomer having four or more ethylenically unsaturated double bonds is not suitable, the functional group density is particularly high. When it is not in an appropriate range, the sensitivity as a black coloring composition is insufficient, or the patterning property is poor. On the other hand, when the blending ratio of each component in the black colored composition is appropriate, both high sensitivity and good patternability can be achieved. The dispersion stability and patterning property of the black colored composition are greatly influenced by the characteristics and ratios of the photosensitive transparent resin and the non-photosensitive transparent resin blended in the black colored composition, and Examples 18, 19, 21, 24 ~ 26 etc., using a photosensitive transparent resin and a non-photosensitive transparent resin excellent in dispersibility, and blending an appropriate amount of the photosensitive transparent resin in a well-balanced manner, both dispersion stability and good patterning properties are achieved. . Moreover, the black coating film excellent in the solvent resistance which has not been able to be obtained was able to be obtained by mix | blending a photosensitive transparent resin in a proper quantity in a black coloring composition.
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