JP4873043B2 - Photosensitive resin composition, photosensitive element using the same, method for forming partition of image display device, and method for manufacturing image display device - Google Patents
Photosensitive resin composition, photosensitive element using the same, method for forming partition of image display device, and method for manufacturing image display device Download PDFInfo
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- JP4873043B2 JP4873043B2 JP2009109103A JP2009109103A JP4873043B2 JP 4873043 B2 JP4873043 B2 JP 4873043B2 JP 2009109103 A JP2009109103 A JP 2009109103A JP 2009109103 A JP2009109103 A JP 2009109103A JP 4873043 B2 JP4873043 B2 JP 4873043B2
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- Prior art keywords
- resin composition
- photosensitive resin
- image display
- display device
- meth
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- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 19
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- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
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Landscapes
- Materials For Photolithography (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
Description
本発明は、感光性樹脂組成物、これを用いた感光性エレメント、画像表示装置の隔壁の形成方法及び画像表示装置の製造方法に関する。 The present invention relates to a photosensitive resin composition, a photosensitive element using the same, a method for forming partition walls of an image display device, and a method for manufacturing an image display device.
近年、紙のように薄く、持ち運びが自由で、文字や画像が表示可能な画像表示装置（ＰＬＤ：Ｐａｐｅｒ Ｌｉｋｅ Ｄｉｓｐｌａｙ）が注目を集めている。かかる画像表示装置は、通常の印刷物としての紙の長所である視認性、携帯性を有し、さらに、情報を電気的に書き換え可能であるため、環境やコストの面からも紙の代替品として実用化が試みられている。
画像表示装置の表示技術としては、電気泳動などにより粒子を移動させるタイプ、液晶タイプ、電気化学タイプなど様々なタイプが考案されている（例えば、非特許文献１参照）。
特に粒子を移動させるタイプとしては、マイクロカプセル型電気泳動方式、マイクロカップ型電気泳動方式、電子粉流体方式、トナーディスプレイ等の方式が検討されている。これらの方式では、透明電極間に表示媒体である白と黒の粒子を封入し電場をかけ、これらの粒子を電気的に移動させることにより白／黒画像を形成し表示させる。
2. Description of the Related Art In recent years, an image display device (PLD: Paper Like Display) that is as thin as paper, can be freely carried, and can display characters and images has attracted attention. Such an image display device has visibility and portability, which are the advantages of paper as a normal printed matter, and is capable of electrically rewriting information, so that it can be used as an alternative to paper in terms of environment and cost. Practical application is being attempted.
As a display technique of an image display device, various types such as a type in which particles are moved by electrophoresis, a liquid crystal type, an electrochemical type, and the like have been devised (for example, see Non-Patent Document 1).
In particular, as a type for moving particles, methods such as a microcapsule electrophoresis method, a microcup electrophoresis method, an electronic powder fluid method, and a toner display have been studied. In these systems, white and black particles as a display medium are sealed between transparent electrodes, an electric field is applied, and these particles are electrically moved to form and display a white / black image.
上記粒子移動タイプの画像表示装置の場合、上述のように白／黒の粒子を封入するための隔壁が必要となる。かかる隔壁の形成方法としては、金型転写法、スクリーン印刷法、サンドブラスト法、フォトリソ法、アディティブ法等が提案されている（例えば、特許文献１参照）。中でも、感光性樹脂組成物を用いて、活性光線の照射により高精細なパターンが効率よく形成できるフォトリソ法が注目されている。
また、最近では、白／黒画像表示にカラーフィルターを組み合わせることにより、フルカラー表示を実現させるという報告例もある（例えば、非特許文献２参照）。
かかるフルカラー表示を行う際、白／黒表示の画像表示装置にカラーフィルターを併用するため、各画素間のコントラストの向上が必須である。従って、各画素間の光を遮断するための遮光層が必要となる。
In the case of the particle movement type image display device, a partition for enclosing white / black particles as described above is required. As a method for forming such partition walls, a mold transfer method, a screen printing method, a sand blast method, a photolithography method, an additive method, and the like have been proposed (for example, see Patent Document 1). Among these, a photolithographic method that can form a high-definition pattern efficiently by irradiation with actinic rays using a photosensitive resin composition has attracted attention.
Recently, there is a report example of realizing full color display by combining a color filter with white / black image display (see, for example, Non-Patent Document 2).
When performing such full-color display, a color filter is used in combination with a white / black display image display device, and thus it is essential to improve the contrast between pixels. Therefore, a light shielding layer for shielding light between the pixels is required.
フォトリソ法を用いた画像表示装置の隔壁は、以下のようにして形成される。すなわち、基板上にブラックマトリックスと呼ばれる遮光層をフォトリソ技術により積層する工程、さらに前記遮光層上に感光性樹脂組成物を塗布、又は感光性フィルムを積層することにより感光性樹脂組成物層を形成する工程、前記感光性樹脂組成物層の所定部分に活性光線を照射して露光部を光硬化させる工程、未露光部を除去して光硬化物パターンを形成する工程を含む。従って、画像表示装置の隔壁を形成するための感光性樹脂組成物には、一般に、感度、解像性及び基板への密着性が要求される。 The partition walls of the image display device using the photolithography method are formed as follows. That is, a step of laminating a light-shielding layer called a black matrix on a substrate by photolithography, and further forming a photosensitive resin composition layer by applying a photosensitive resin composition or laminating a photosensitive film on the light-shielding layer A step of irradiating a predetermined portion of the photosensitive resin composition layer with actinic rays to photocure the exposed portion, and a step of removing the unexposed portion to form a photocured product pattern. Therefore, in general, the photosensitive resin composition for forming the partition walls of the image display device is required to have sensitivity, resolution, and adhesion to the substrate.
画像表示装置を製造する場合、前記工程で得たパターン内に粒子等の表示媒体を充填する工程、前記光硬化物パターンを熱処理する工程、電極基板を貼り付ける工程などをさらに含む。これにより、感光性樹脂組成物層の硬化物を隔壁とする画像表示装置が得られる。前記工程においては高温プロセスが必須となるため、感光性樹脂組成物を用いて形成される画像表示装置の隔壁には、耐熱性、アウトガス成分の減少等が要求される。 When manufacturing an image display device, the method further includes a step of filling a display medium such as particles in the pattern obtained in the step, a step of heat-treating the photocured product pattern, a step of attaching an electrode substrate, and the like. Thereby, the image display apparatus which uses the hardened | cured material of the photosensitive resin composition layer as a partition is obtained. Since a high temperature process is indispensable in the above process, heat resistance, reduction of outgas components, and the like are required for the partition walls of the image display device formed using the photosensitive resin composition.
従来の感光性樹脂組成物を用いた画像表示装置の隔壁の形成方法では、上述のように遮光層と隔壁を各々積層する必要があるため工程数が増え、材料のコストが高くなるといった問題があった。
また、従来の感光性樹脂組成物を用いて遮光性の隔壁を形成した場合、活性光線が遮光性を有する感光性樹脂組成物に吸収されるため、底部まで活性光線が届かず解像度及び基板への密着性が不十分であった。
また、従来の感光性樹脂組成物を用いて隔壁を形成した場合、隔壁からアウトガスが発生し、表示特性を悪化するという問題があった。
本発明は、遮光性を有し、解像度及び基板への密着性が良好な画像表示装置用の隔壁を、簡便に作業性よく形成することができる感光性樹脂組成物、これを用いた感光性エレメント、画像表示装置の隔壁の形成方法及び画像表示装置の製造方法を提供する。
In the conventional method for forming a partition wall of an image display device using a photosensitive resin composition, it is necessary to laminate a light shielding layer and a partition wall as described above, which increases the number of processes and increases the cost of materials. there were.
In addition, when a light-shielding partition is formed using a conventional photosensitive resin composition, actinic rays are absorbed by the photosensitive resin composition having a light-shielding property. The adhesiveness of was insufficient.
Moreover, when the partition was formed using the conventional photosensitive resin composition, there existed a problem that an outgas generate | occur | produces from a partition and a display characteristic deteriorates.
The present invention relates to a photosensitive resin composition capable of easily and efficiently forming a partition wall for an image display device having light-shielding properties and good resolution and adhesion to a substrate, and photosensitive property using the same. An element, a method of forming a partition wall of an image display device, and a method of manufacturing an image display device are provided.
本発明は、画像表示装置の隔壁を形成するための感光性樹脂組成物であって、前記感光性樹脂組成物が、（Ａ）（メタ）アクリル酸ブチル及び（メタ）アクリル酸を単量体単位として有するバインダーポリマー、（Ｂ）光重合性化合物、（Ｃ）光重合開始剤、（Ｄ）黒色顔料を含み、前記（Ｃ）光重合開始剤が、下記一般式（Ｉ）で表わされる化合物、及び下記一般式（ＩＩ）で表わされる化合物を含有する感光性樹脂組成物を提供する。 The present invention relates to a photosensitive resin composition for forming partition walls of an image display device, wherein the photosensitive resin composition is a monomer of (A) butyl (meth) acrylate and (meth) acrylic acid. Binder polymer as unit, (B) photopolymerizable compound, (C) photopolymerization initiator, (D) black pigment, wherein (C) photopolymerization initiator is represented by the following general formula (I) And a photosensitive resin composition containing a compound represented by the following general formula (II).
また、本発明は、前記一般式（Ｉ）で表わされる化合物の含有量が、前記（Ａ）成分及び（Ｂ）成分との総量１００質量部に対して０．０５〜１質量部であり、前記一般式（ＩＩ）で表わされる化合物の含有量が、前記（Ａ）成分及び（Ｂ）成分との総量１００質量部に対して１〜１０質量部を含有する上記に記載の感光性樹脂組成物を提供する。
また、本発明は、前記（Ｄ）黒色顔料がチタンブラックを含む、上記に記載の感光性樹脂組成物を提供する。
本発明の感光性樹脂組成物は上記構成を有することにより、遮光性を有し、表示特性が良好で、解像度及び基板への密着性が良好な画像表示装置用の隔壁を、簡便に作業性よく形成することができる。
In the present invention, the content of the compound represented by the general formula (I) is 0.05 to 1 part by mass with respect to 100 parts by mass of the total amount of the component (A) and the component (B). The photosensitive resin composition as described above, wherein the content of the compound represented by the general formula (II) is 1 to 10 parts by mass with respect to 100 parts by mass of the total amount of the component (A) and the component (B). Offer things.
Moreover, this invention provides the photosensitive resin composition as described above in which the (D) black pigment contains titanium black.
Since the photosensitive resin composition of the present invention has the above-described configuration, the partition for an image display device having light shielding properties, good display characteristics, and good resolution and adhesion to a substrate can be easily obtained. Can be well formed.
また、本発明は、支持体と、該支持体上に形成された前記感光性樹脂組成物からなる感光性樹脂組成物層と、を備える感光性エレメントを提供する。
また、本発明は、前記感光性樹脂組成物層の膜厚が１０〜６０μｍである、上記に記載の感光性エレメントを提供する。
本発明の感光性エレメントは、上記本発明の感光性樹脂組成物からなる感光性樹脂組成物層を備えることにより、遮光性を有し、表示特性が良好で、解像度及び基板への密着性が良好な画像表示装置用の隔壁を、簡便に作業性よく形成することができる。
Moreover, this invention provides a photosensitive element provided with a support body and the photosensitive resin composition layer which consists of the said photosensitive resin composition formed on this support body.
Moreover, this invention provides the photosensitive element as described above whose film thickness of the said photosensitive resin composition layer is 10-60 micrometers.
The photosensitive element of the present invention comprises a photosensitive resin composition layer composed of the photosensitive resin composition of the present invention, so that it has light shielding properties, good display characteristics, resolution and adhesion to a substrate. A good partition wall for an image display device can be easily formed with good workability.
また、本発明は、画像表示装置の基板上に、前記感光性樹脂組成物又は感光性エレメントからなる感光性樹脂組成物層を積層する積層工程と、前記感光性樹脂組成物層の所定部分に活性光線を照射して露光部を光硬化せしめる露光工程と、前記露光部以外の部分を除去して光硬化物パターンを形成する現像工程と、を有する、画像表示装置の隔壁の形成方法を提供する。
また、本発明は、前記画像表示装置の隔壁の形成方法により形成された光硬化物パターンを、６０〜２５０℃で加熱処理して熱硬化せしめる加熱工程をさらに有する、画像表示装置の隔壁の形成方法を提供する。
また、本発明は、表示媒体を、前記画像表示装置の隔壁の形成方法により形成された隔壁内に充填する工程と、一方の基板に対向するように隔壁の反対側に基板を貼り付ける工程と、を有する、画像表示装置の製造方法を提供する。
Further, the present invention provides a laminating step of laminating the photosensitive resin composition layer comprising the photosensitive resin composition or the photosensitive element on the substrate of the image display device, and a predetermined portion of the photosensitive resin composition layer. Provided is a method for forming a partition wall of an image display device, comprising: an exposure step of irradiating an actinic ray to photocure an exposed portion; and a developing step of removing a portion other than the exposed portion to form a photocured product pattern To do.
In addition, the present invention further includes a heating step in which a photocured product pattern formed by the method for forming a partition wall of the image display device is heat-treated at 60 to 250 ° C. to thermally cure the image display device partition wall formation. Provide a method.
The present invention also includes a step of filling a display medium into a partition formed by the method for forming a partition of the image display device, and a step of attaching a substrate to the opposite side of the partition so as to face one substrate. A method for manufacturing an image display device is provided.
本発明によれば、遮光性を有し、表示特性が良好で、解像度及び基板への密着性が良好な画像表示装置用の隔壁を、簡便に作業性よく形成することが可能となる。 According to the present invention, it is possible to easily and efficiently form a partition wall for an image display device that has light shielding properties, good display characteristics, and good resolution and adhesion to a substrate.
以下、本発明の好適な実施形態について説明する。なお、本明細書における（メタ）アクリル酸とはアクリル酸及びそれに対応するメタクリル酸を意味し、（メタ）アクリレートとはアクリレート及びそれに対応するメタクリレートを意味し、（メタ）アクリロイルとはアクリロイル及びそれに対応するメタクリロイルを意味する。 Hereinafter, preferred embodiments of the present invention will be described. In this specification, (meth) acrylic acid means acrylic acid and methacrylic acid corresponding thereto, (meth) acrylate means acrylate and corresponding methacrylate, and (meth) acryloyl means acryloyl and it. Means the corresponding methacryloyl.
本発明の感光性樹脂組成物は、（Ａ）バインダーポリマー、（Ｂ）光重合性化合物、（Ｃ）光重合開始剤及び（Ｄ）黒色顔料を含有してなる。
以下、各成分について詳細に説明する。
The photosensitive resin composition of the present invention comprises (A) a binder polymer, (B) a photopolymerizable compound, (C) a photopolymerization initiator, and (D) a black pigment.
Hereinafter, each component will be described in detail.
本発明で用いる（Ａ）バインダーポリマーとしては、（メタ）アクリル酸ブチル及び（メタ）アクリル酸を必須の構成成分として含有するバインダーポリマーを用いる。
その他の構成成分の重合性単量体としては、例えば、スチレン、ビニルトルエン、α−メチルスチレン、ｐ−メチルスチレン、ｐ−エチルスチレン等の重合可能なスチレン誘導体、アクリルアミド、アクリロニトリル、ビニル−ｎ−ブチルエーテル等のビニルアルコールのエステル類、（メタ）アクリル酸アルキルエステル、（メタ）アクリル酸テトラヒドロフルフリルエステル、（メタ）アクリル酸ジメチルアミノエチルエステル、（メタ）アクリル酸ジエチルアミノエチルエステル、（メタ）アクリル酸グリシジルエステル、２，２，２−トリフルオロエチル（メタ）アクリレート、２，２，３，３−テトラフルオロプロピル（メタ）アクリレート、α−ブロモ（メタ）アクリル酸、α−クロル（メタ）アクリル酸、β−フリル（メタ）アクリル酸、β−スチリル（メタ）アクリル酸、マレイン酸、マレイン酸無水物、マレイン酸モノメチル、マレイン酸モノエチル、マレイン酸モノイソプロピル等のマレイン酸モノエステル、フマール酸、ケイ皮酸、α−シアノケイ皮酸、イタコン酸、クロトン酸、プロピオール酸などが挙げられる。
（Ａ）バインダーポリマーは、アルカリ現像性の見地から、カルボキシル基を含有していることが好ましく、（メタ）アクリル酸と他のカルボキシル基を有する重合性単量体とその他の重合性単量体をラジカル重合させることにより製造することができる。
（Ａ）バインダーポリマーの酸価は、解像性の観点から３０ｍｇＫＯＨ／ｇ以上であることが好ましく、耐現像液性及び密着性の観点から２５０ｍｇＫＯＨ／ｇ以下であることが好ましく、８０〜２４０ｍｇＫＯＨ／ｇであることがより好ましく、１３０〜２３０ｍｇＫＯＨ／ｇであることがさらに好ましく、１８０〜２２０ｍｇＫＯＨ／ｇであることが特に好ましい。現像工程として溶剤による現像を行う場合は、カルボキシル基を有する重合性単量体の使用量を抑えて調製することが好ましい。バインダーポリマー中、（メタ）アクリル酸ブチル及び（メタ）アクリル酸の含有量は、バインダーポリマーを構成する単量体の総量１００質量部に対して、（メタ）アクリル酸を、２０〜４０質量部、（メタ）アクリル酸ブチル２０〜５０重量部、その他の重合性単量体を２０〜５０重量部の割合で配合することが好ましい。
As the (A) binder polymer used in the present invention, a binder polymer containing butyl (meth) acrylate and (meth) acrylic acid as essential components is used.
Examples of other polymerizable components include polymerizable styrene derivatives such as styrene, vinyl toluene, α-methyl styrene, p-methyl styrene, p-ethyl styrene, acrylamide, acrylonitrile, vinyl-n-. Esters of vinyl alcohol such as butyl ether, (meth) acrylic acid alkyl ester, (meth) acrylic acid tetrahydrofurfuryl ester, (meth) acrylic acid dimethylaminoethyl ester, (meth) acrylic acid diethylaminoethyl ester, (meth) acrylic Acid glycidyl ester, 2,2,2-trifluoroethyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, α-bromo (meth) acrylic acid, α-chloro (meth) acrylic Acid, β-furyl (meth) a Maleic acid monoesters such as lauric acid, β-styryl (meth) acrylic acid, maleic acid, maleic anhydride, monomethyl maleate, monoethyl maleate, monoisopropyl maleate, fumaric acid, cinnamic acid, α-cyanocinnamic Acid, itaconic acid, crotonic acid, propiolic acid and the like can be mentioned.
(A) The binder polymer preferably contains a carboxyl group from the viewpoint of alkali developability, and (meth) acrylic acid and other polymerizable monomers having a carboxyl group and other polymerizable monomers. Can be produced by radical polymerization.
(A) The acid value of the binder polymer is preferably 30 mgKOH / g or more from the viewpoint of resolution, preferably 250 mgKOH / g or less from the viewpoint of developer resistance and adhesion, and 80 to 240 mgKOH / g. g is more preferable, 130 to 230 mgKOH / g is further preferable, and 180 to 220 mgKOH / g is particularly preferable. When performing development with a solvent as the development step, it is preferable to prepare while suppressing the amount of polymerizable monomer having a carboxyl group. In the binder polymer, the content of butyl (meth) acrylate and (meth) acrylic acid is 20 to 40 parts by mass of (meth) acrylic acid with respect to 100 parts by mass of the total amount of monomers constituting the binder polymer. It is preferable to blend 20 to 50 parts by weight of butyl (meth) acrylate and 20 to 50 parts by weight of other polymerizable monomers.
（Ａ）バインダーポリマーの重量平均分子量（ゲルパーミエーションクロマトグラフィー（ＧＰＣ）で測定し、標準ポリスチレンを用いた検量線により換算）は、耐現像液性の観点から２０，０００以上であることが好ましく、現像時間を短くできる観点から３００，０００以下であることが好ましく、２５，０００〜１５０，０００であることがより好ましく、３０，０００〜１００，０００であることが特に好ましい。
これらのうち、メタクリル酸、メタクリル酸メチル、メタクリル酸ブチルを含有するアクリルコポリマーは、現像性、解像性などの点から好ましい結果を得ることができる。その他の成分として他の共重合可能な成分を用いることができる。
(A) The weight average molecular weight of the binder polymer (measured by gel permeation chromatography (GPC) and converted by a calibration curve using standard polystyrene) is preferably 20,000 or more from the viewpoint of developer resistance. From the viewpoint of shortening the development time, it is preferably 300,000 or less, more preferably 25,000 to 150,000, and particularly preferably 30,000 to 100,000.
Among these, acrylic copolymers containing methacrylic acid, methyl methacrylate, and butyl methacrylate can obtain preferable results from the viewpoints of developability and resolution. As other components, other copolymerizable components can be used.
バインダーポリマーとしては、本発明の特性を損なわない範囲で、例えばアクリル系樹脂、スチレン系樹脂、エポキシ系樹脂、アミド系樹脂、アミドエポキシ系樹脂、アルキド系樹脂、フェノール系樹脂等を用いても良い。アルカリ現像性の観点からは、アクリル系樹脂が好ましい。これらは単独で、または２種類以上のバインダーポリマーを組み合わせて用いることができる。２種類以上のバインダーポリマーの組み合わせの例としては、異なる共重合成分からなる２種類以上のバインダーポリマー、異なる重量平均分子量の２種類以上のバインダーポリマー、異なる分散度の２種類以上のバインダーポリマーなどが挙げられる。また、特開平１１−３２７１３７号公報記載のマルチモード分子量分布を有するポリマーを使用することもできる。なお、必要に応じて、バインダーポリマーは感光性基を有していてもよい。 As the binder polymer, for example, an acrylic resin, a styrene resin, an epoxy resin, an amide resin, an amide epoxy resin, an alkyd resin, a phenol resin, or the like may be used as long as the characteristics of the present invention are not impaired. . An acrylic resin is preferable from the viewpoint of alkali developability. These can be used alone or in combination of two or more binder polymers. Examples of combinations of two or more types of binder polymers include two or more types of binder polymers composed of different copolymer components, two or more types of binder polymers having different weight average molecular weights, and two or more types of binder polymers having different degrees of dispersion. Can be mentioned. A polymer having a multimode molecular weight distribution described in JP-A No. 11-327137 can also be used. In addition, the binder polymer may have a photosensitive group as necessary.
（Ａ）成分のバインダーポリマーは、例えば、常法により重合性単量体をラジカル重合させることにより製造することができる。 The binder polymer of component (A) can be produced, for example, by radical polymerization of a polymerizable monomer by a conventional method.
本発明で（Ｂ）成分として用いられる光重合性化合物としては、例えば、ポリエチレングリコールジ（メタ）アクリレート（エチレン基の数が２〜１４のもの）、トリメチロールプロパンジ（メタ）アクリレート、トリメチロールプロパントリ（メタ）アクリレート、トリメチロールプロパンエトキシトリ（メタ）アクリレート、トリメチロールプロパンプロポキシトリ（メタ）アクリレート、テトラメチロールメタントリ（メタ）アクリレート、テトラメチロールメタンテトラ（メタ）アクリレート、ポリプロピレングリコールジ（メタ）アクリレート（プロピレン基の数が２〜１４のもの）、ジペンタエリスリトールペンタ（メタ）アクリレート、ジペンタエリスリトールヘキサ（メタ）アクリレート等の多価アルコールにα、β−不飽和カルボン酸を反応させて得られる化合物、ビスフェノールＡジオキシエチレンジ（メタ）アクリレート、ビスフェノールＡトリオキシエチレンジ（メタ）アクリレート、ビスフェノールＡデカオキシエチレンジ（メタ）アクリレート等のビスフェノールＡジオキシエチレンジ（メタ）アクリレート、トリメチロールプロパントリグリシジルエーテルトリアクリルレート、ビスフェノールＡジグリシジルエーテルアクリレート等のグリシジル基含有化合物にα、β−不飽和カルボン酸を付加して得られる化合物、無水フタル酸等の多価カルボン酸とβ−ヒドロキシエチル（メタ）アクリレート等の水酸基及びエチレン性不飽和基を有する物質とのエステル化物、（メタ）アクリル酸メチルエステル、（メタ）アクリル酸エチルエステル、（メタ）アクリル酸ブチルエステル、（メタ）アクリル酸２−エチルヘキシルエステル等の（メタ）アクリル酸のアルキルエステル、トリレンジイソシアネートと２−ヒドロキシエチル（メタ）アクリル酸エステルとの反応物、トリメチルヘキサメチレンジイソシアネートとシクロヘキサンジメタノールと２−ヒドロキシエチル（メタ）アクリル酸エステルとの反応物等のウレタン（メタ）アクリレートなどが挙げられる。 Examples of the photopolymerizable compound used as the component (B) in the present invention include polyethylene glycol di (meth) acrylate (having 2 to 14 ethylene groups), trimethylolpropane di (meth) acrylate, and trimethylol. Propane tri (meth) acrylate, trimethylolpropane ethoxytri (meth) acrylate, trimethylolpropane propoxytri (meth) acrylate, tetramethylolmethane tri (meth) acrylate, tetramethylolmethane tetra (meth) acrylate, polypropylene glycol di (meth) ) Α, β-unsaturated polyhydric alcohols such as acrylates (having 2 to 14 propylene groups), dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, etc. Compounds obtained by reacting carboxylic acid, bisphenol A dioxyethylene di (meth) acrylate, bisphenol A dioxyethylene di (meth) acrylate, bisphenol A dioxyethylene di (meth) acrylate, bisphenol A dioxyethylene di (meth) acrylate, etc. A compound obtained by adding an α, β-unsaturated carboxylic acid to a glycidyl group-containing compound such as (meth) acrylate, trimethylolpropane triglycidyl ether triacrylate, bisphenol A diglycidyl ether acrylate, and many other compounds such as phthalic anhydride Esterified product of a carboxylic acid and a substance having an ethylenically unsaturated group such as β-hydroxyethyl (meth) acrylate, (meth) acrylic acid methyl ester, (meth) acrylic acid ethyl ester, (meth) Butyl acrylate, alkyl (meth) acrylate such as 2-ethylhexyl (meth) acrylate, reaction product of tolylene diisocyanate and 2-hydroxyethyl (meth) acrylate, trimethylhexamethylene diisocyanate and cyclohexane Examples include urethane (meth) acrylate such as a reaction product of dimethanol and 2-hydroxyethyl (meth) acrylic acid ester.
本発明に用いられる（Ｃ）成分として用いられる前記一般式（Ｉ）で表わされる光重合開始剤としては、例えば、１，６−ビス（９−アクリジニル）ヘキサン、１，７−ビス（９−アクリジニル）ヘプタン、１，８−ビス（９−アクリジニル）オクタン、１，９−ビス（９−アクリジニル）ノナン、１，１０−ビス（９−アクリジニル）デカン、１，１１−ビス（９−アクリジニル）ウンデカン、１，１２−ビス（９−アクリジニル）ドデカン等があげられる。 Examples of the photopolymerization initiator represented by the general formula (I) used as the component (C) used in the present invention include 1,6-bis (9-acridinyl) hexane, 1,7-bis (9- Acridinyl) heptane, 1,8-bis (9-acridinyl) octane, 1,9-bis (9-acridinyl) nonane, 1,10-bis (9-acridinyl) decane, 1,11-bis (9-acridinyl) Examples include undecane and 1,12-bis (9-acridinyl) dodecane.
（Ｃ）成分である前記一般式（Ｉ）で表わされる光重合開始剤（アクリジン化合物）は、例えば、ジフェニルアミンと二価カルボン酸を金属酸化物の存在下に反応させることによって容易に製造することができる。
前記（Ｃ）成分として用いられる前記一般式（Ｉ）は、前記（Ａ）成分と（Ｂ）成分の総量１００質量部に対し０．０５〜１質量部、好ましくは０．１〜０．５質量部の範囲で用いられる。０．０５質量部未満では充分な光感度が得られず、１質量部を超えて使用すると、それ以上感度は向上しない。
The photopolymerization initiator (acridine compound) represented by the general formula (I) as the component (C) can be easily produced by, for example, reacting diphenylamine and a divalent carboxylic acid in the presence of a metal oxide. Can do.
The said general formula (I) used as said (C) component is 0.05-1 mass part with respect to 100 mass parts of total amounts of the said (A) component and (B) component, Preferably it is 0.1-0.5. Used in the range of parts by mass. If it is less than 0.05 part by mass, sufficient photosensitivity cannot be obtained, and if it is used in excess of 1 part by mass, the sensitivity is not further improved.
また、本発明に用いられる（Ｃ）成分として用いられる前記一般式（ＩＩ）で表わされる光重合開始剤としては、例えば、１−（４−メトキシフェニル）−２，２−ジメトキシ−２−フェニル−１−エタノン、１−（４−メトキシフェニル）−２−メトキシ−２−エトキシ−２−フェニル−１−エタノン、１−（４−メトキシフェニル）−２−メトキシ−２−プロポキシ−２−フェニル−１−エタノン、下記の式で示される２，２−ジメトキシ−１，２−ジフェニル−１−エタノン（通称ベンジルジメチルケタール）等があげられる。これらの中でもベンジルジメチルケタールが特に好ましい。 Examples of the photopolymerization initiator represented by the general formula (II) used as the component (C) used in the present invention include 1- (4-methoxyphenyl) -2,2-dimethoxy-2-phenyl. -1-ethanone, 1- (4-methoxyphenyl) -2-methoxy-2-ethoxy-2-phenyl-1-ethanone, 1- (4-methoxyphenyl) -2-methoxy-2-propoxy-2-phenyl Examples include -1-ethanone and 2,2-dimethoxy-1,2-diphenyl-1-ethanone (commonly called benzyldimethyl ketal) represented by the following formula. Of these, benzyldimethyl ketal is particularly preferred.
本発明の（Ｄ）成分の黒色顔料として用いられる化合物としては、例えば、チタンブラック、カーボンブラック、コバルトブラック等の無機系黒色顔料が挙げられ、活性光線の照射を行う観点から、チタンブラックが好ましい。
前記（Ｄ）成分は、感光性樹脂組成物の遮光性、密着性、解像性の観点から、（Ａ）成分及び（Ｂ）成分の総量１００質量部に対して、０．１〜１０質量部好ましくは、０．２〜５質量部の範囲で用いられる。１０質量部を超えると活性光線の吸収が著しく解像しない。０．１質量部未満では充分な遮光性が得られなくなる。
Examples of the compound used as the black pigment of the component (D) of the present invention include inorganic black pigments such as titanium black, carbon black, and cobalt black, and titanium black is preferable from the viewpoint of irradiation with actinic rays. .
The component (D) is 0.1 to 10 parts by mass with respect to 100 parts by mass of the total amount of the component (A) and the component (B) from the viewpoints of light shielding properties, adhesion, and resolution of the photosensitive resin composition. Part: Preferably, it is used in the range of 0.2 to 5 parts by mass. When the amount exceeds 10 parts by mass, the absorption of actinic rays is not significantly resolved. If the amount is less than 0.1 parts by mass, sufficient light shielding properties cannot be obtained.
以上のような成分を含む樹脂組成物は、さらに必要に応じて、マラカイトグリーン等の染料、トリブロモフェニルスルホン、ロイコクリスタルバイオレット等の光発色剤、熱発色防止剤、ｐ−トルエンスルホンアミド等の可塑剤、顔料、充填剤、消泡剤、難燃剤、安定剤、密着性付与剤、レベリング剤、剥離促進剤、酸化防止剤、香料、イメージング剤、熱架橋剤などを、（Ａ）成分および（Ｂ）成分の総量１００質量部に対して各々０．０１〜２０質量部程度含有することができる。これらは単独で、または２種類以上を組み合わせて使用される。 The resin composition containing the components as described above may further include a dye such as malachite green, a photochromic agent such as tribromophenyl sulfone or leuco crystal violet, a thermochromic inhibitor, p-toluenesulfonamide or the like, if necessary. Plasticizers, pigments, fillers, antifoaming agents, flame retardants, stabilizers, adhesion-imparting agents, leveling agents, peeling accelerators, antioxidants, fragrances, imaging agents, thermal crosslinking agents, etc. (B) About 0.01-20 mass parts can each be contained with respect to 100 mass parts of total amounts of a component. These may be used alone or in combination of two or more.
以上のような成分を含む本発明の感光性樹脂組成物は、たとえば、含有成分をロールミル、ビーズミル等で均一に混練、混合することにより得ることができる。また、必要に応じて、メタノール、エタノール、アセトン、メチルエチルケトン、メチルセロソルブ、エチルセロソルブ、トルエン、Ｎ，Ｎ−ジメチルホルムアミド、プロピレングリコールモノメチルエーテル等の溶剤またはこれらの混合溶剤に溶解して、固形分３０〜６０質量％程度の溶液として用いることができる。 The photosensitive resin composition of the present invention containing the components as described above can be obtained, for example, by uniformly kneading and mixing the contained components with a roll mill, a bead mill or the like. If necessary, it can be dissolved in a solvent such as methanol, ethanol, acetone, methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, toluene, N, N-dimethylformamide, propylene glycol monomethyl ether, or a mixed solvent thereof to obtain a solid content of 30 It can be used as a solution of about ˜60% by mass.
得られた感光性樹脂組成物を用いて画像表示装置用基板上に感光物組成物層を形成する方法としては、特に制限はないが、前記基板上に感光性樹脂組成物を液状レジストとして塗布して乾燥することができる。また、必要に応じて感光性樹脂組成物層上に保護フィルムを被覆することができる。さらに、後に詳しく述べるが感光性樹脂組成物層を感光性エレメントの形態で用いることが好ましい。塗布される感光性樹脂組成物層の厚みは、用途により異なるが、乾燥後の厚みで１〜１００μｍ、好ましくは１０〜６０μｍであることが好ましい。液状レジストとして塗布後、保護フィルムを被覆して用いる場合の保護フィルムとしては、たとえば、ポリエチレン、ポリプロピレン等の重合体フィルムが挙げられる。 A method for forming a photosensitive material composition layer on a substrate for an image display device using the obtained photosensitive resin composition is not particularly limited, but the photosensitive resin composition is applied as a liquid resist on the substrate. And can be dried. Moreover, a protective film can be coat | covered on the photosensitive resin composition layer as needed. Further, as will be described in detail later, it is preferable to use the photosensitive resin composition layer in the form of a photosensitive element. Although the thickness of the photosensitive resin composition layer to be applied varies depending on the use, it is preferably 1 to 100 μm, preferably 10 to 60 μm, after drying. Examples of the protective film in the case where the protective film is used after being coated as a liquid resist include polymer films such as polyethylene and polypropylene.
本発明の感光性エレメントは、支持体と、その上に形成された上記感光性樹脂組成物からなる感光性樹脂組成物層とを備える。
支持体としては、たとえば、ポリエチレンテレフタレート等のポリエステル、ポリプロピレン、ポリエチレン等の重合体フィルムを好ましく用いることができる。重合体フィルムの厚みは、１〜１００μｍ程度とすることが好ましく、５〜５０μｍであることがより好ましく、１０〜３０μｍであることがさらに好ましい。
The photosensitive element of this invention is equipped with the support body and the photosensitive resin composition layer which consists of the said photosensitive resin composition formed on it.
As the support, for example, a polyester film such as polyethylene terephthalate, or a polymer film such as polypropylene or polyethylene can be preferably used. The thickness of the polymer film is preferably about 1 to 100 μm, more preferably 5 to 50 μm, and still more preferably 10 to 30 μm.
支持体上への感光性樹脂組成物層の形成方法は、特に制限されないが、感光性樹脂組成物の溶液を塗布、乾燥することにより好ましく実施できる。塗布される感光性樹脂組成物層の厚みは、用途により異なるが、乾燥後の厚みで１〜１００μｍ程度であることが好ましい。画像表示装置の隔壁として用いる場合、感光性樹脂組成物層の厚みは、乾燥後の厚みで１０〜７０μｍであることがより好ましく、１０〜６０μｍであることがさらに好ましい。
塗布は、たとえば、ロールコータ、コンマコータ、グラビアコータ、エアーナイフコータ、ダイコータ、バーコータ等の公知の方法で行うことができる。乾燥は、７０〜１５０℃、５〜３０分間程度で行うことができる。また、感光性樹脂組成物層中の残存有機溶剤量は、後の工程での有機溶剤の拡散を防止する点から、２質量％以下とすることが好ましい。
Although the formation method in particular of the photosensitive resin composition layer on a support body is not restrict | limited, It can implement preferably by apply | coating and drying the solution of the photosensitive resin composition. The thickness of the photosensitive resin composition layer to be applied varies depending on the use, but is preferably about 1 to 100 μm after drying. When used as a partition wall of an image display device, the thickness of the photosensitive resin composition layer is more preferably 10 to 70 μm, and further preferably 10 to 60 μm in terms of the thickness after drying.
The coating can be performed by a known method such as a roll coater, a comma coater, a gravure coater, an air knife coater, a die coater, or a bar coater. Drying can be performed at 70 to 150 ° C. for about 5 to 30 minutes. Further, the amount of the remaining organic solvent in the photosensitive resin composition layer is preferably 2% by mass or less from the viewpoint of preventing diffusion of the organic solvent in the subsequent step.
支持体として用いられる上記重合体フィルムを保護フィルムとして用いて、感光性樹脂組成物層表面を被覆してもよい。保護フィルムとしては、感光性樹脂組成物層と支持体の接着力よりも、感光性樹脂組成物層と保護フィルムの接着力の方が小さいものが好ましく、また、低フィッシュアイのフィルムが好ましい。さらに、感光性フィルムは、感光性樹脂組成物層、支持体および任意の保護フィルムの他に、クッション層、接着層、光吸収層、ガスバリア層等の中間層や保護層を有していてもよい。 You may coat | cover the photosensitive resin composition layer surface using the said polymer film used as a support body as a protective film. As the protective film, those having a smaller adhesive force between the photosensitive resin composition layer and the protective film than the adhesive force between the photosensitive resin composition layer and the support are preferable, and a film having a low fish eye is preferable. Furthermore, the photosensitive film may have an intermediate layer and a protective layer such as a cushion layer, an adhesive layer, a light absorption layer, and a gas barrier layer in addition to the photosensitive resin composition layer, the support, and any protective film. Good.
製造された感光性エレメントは、通常、円筒状の巻芯に巻きとって貯蔵される。なお、この際支持体が外側になるように巻き取られることが好ましい。上記ロール状の感光性エレメントロールの端面には、端面保護の見地から端面セパレータを設置することが好ましく、耐エッジフュージョンの見地から防湿端面セパレータを設置することが好ましい。また、梱包方法として、透湿性の小さいブラックシートに包んで包装することが好ましい。上記巻芯としては、たとえば、ポリエチレン樹脂、ポリプロピレン樹脂、ポリスチレン樹脂、ポリ塩化ビニル樹脂、ＡＢＳ樹脂（アクリロニトリル−ブタジエン−スチレン共重合体）等のプラスチックが挙げられる。 The manufactured photosensitive element is usually wound around a cylindrical core and stored. In addition, it is preferable to wind up so that a support body may become an outer side at this time. An end face separator is preferably installed on the end face of the roll-shaped photosensitive element roll from the viewpoint of end face protection, and a moisture-proof end face separator is preferably installed from the viewpoint of edge fusion resistance. Moreover, as a packing method, it is preferable to wrap and package in a black sheet with low moisture permeability. Examples of the core include plastics such as polyethylene resin, polypropylene resin, polystyrene resin, polyvinyl chloride resin, and ABS resin (acrylonitrile-butadiene-styrene copolymer).
次に、本発明の画像表示装置の隔壁の形成方法について説明する。すなわち、画像表示装置の基板上に、感光性樹脂組成物、又は感光性エレメントを用いて感光性樹脂組成物層を積層する積層工程と、前記感光性樹脂組成物層の所定部分に活性光線を照射して露光部を光硬化せしめる露光工程と、前記露光部以外の部分を除去して光硬化物パターンを形成する現像工程と、を有する。 Next, a method for forming the partition wall of the image display device of the present invention will be described. That is, a lamination step of laminating a photosensitive resin composition layer using a photosensitive resin composition or a photosensitive element on a substrate of an image display device, and an actinic ray at a predetermined portion of the photosensitive resin composition layer An exposure step of irradiating and photocuring the exposed portion, and a developing step of removing a portion other than the exposed portion to form a photocured product pattern.
まず、上述した本発明の感光性樹脂組成物層を画像表示装置の基板上に積層する。前記基板としては、ガラス基板若しくはポリマー基板のような絶縁基板又はシリコン基板などの半導体基板若しくはＩＴＯのような電極が形成された上記基板、半導体基板が挙げられる。積層方法としては、上述した塗布方法が用いられる他、感光性エレメントを用いることもできる。 First, the above-described photosensitive resin composition layer of the present invention is laminated on a substrate of an image display device. Examples of the substrate include an insulating substrate such as a glass substrate or a polymer substrate, a semiconductor substrate such as a silicon substrate, the above-described substrate on which an electrode such as ITO is formed, and a semiconductor substrate. As a lamination method, the above-described coating method is used, and a photosensitive element can also be used.
感光性エレメントを用いる積層方法は、感光性樹脂組成物層上に保護フィルムが存在している場合には、保護フィルムを除去しながら基板上へ積層する。前記積層条件としては、例えば、感光性樹脂組成物層を７０〜１３０℃程度に加熱しながら、基板上に０．１〜１ＭＰａ程度（１〜１０ｋｇｆ／ｃｍ２程度）の圧力で圧着することにより積層する方法などが挙げられ、減圧下で積層することも可能である。基板表面の形状は、通常は平坦であるが、必要に応じて凹凸や電極パターンが形成されていてもよい。 In the laminating method using the photosensitive element, when a protective film is present on the photosensitive resin composition layer, it is laminated on the substrate while removing the protective film. As the lamination condition, for example, by heating the photosensitive resin composition layer to about 70 to 130 ° C., pressure bonding is performed on the substrate at a pressure of about 0.1 to 1 MPa (about 1 to 10 kgf / cm 2 ). The method of laminating etc. is mentioned, and it is also possible to laminate under reduced pressure. The shape of the substrate surface is usually flat, but irregularities and electrode patterns may be formed as necessary.
感光性樹脂組成物の積層後、感光性樹脂組成物層に画像状に活性光線を照射して、露光部を光硬化させる。画像状に活性光線を照射させる方法としては、感光性樹脂組成物層上にマスクパターンを設置して画像状に活性光線を照射し、露光部の感光性樹脂組成物層を光硬化させる方法がある。マスクパターンは、ネガ型でもポジ型でもよく、一般に用いられているものを使用できる。活性光線の光源としては、公知の光源、たとえば、カーボンアーク灯、水銀蒸気アーク灯、高圧水銀灯、キセノンランプ等の紫外線、可視光などを有効に放射するものが用いられる。また、露光方法としては、マスクパターンを用いずにレーザーで直接パターンを描画する、直接描画露光法を用いることもできる。 After lamination of the photosensitive resin composition, the photosensitive resin composition layer is irradiated with an actinic ray in an image form to photocur the exposed portion. As a method of irradiating actinic rays in an image form, there is a method of setting a mask pattern on the photosensitive resin composition layer and irradiating the image form with an actinic ray and photocuring the photosensitive resin composition layer in the exposed portion. is there. The mask pattern may be a negative type or a positive type, and a commonly used one can be used. As the light source of actinic light, a known light source, for example, a light source that effectively emits ultraviolet light, visible light, or the like, such as a carbon arc lamp, a mercury vapor arc lamp, a high-pressure mercury lamp, or a xenon lamp is used. As an exposure method, a direct drawing exposure method in which a pattern is directly drawn with a laser without using a mask pattern can also be used.
露光後に未露光部の感光性樹脂組成物層を現像により選択的に除去することにより、画像表示装置用の基板上に光硬化物パターンが形成される。なお現像工程は、支持体が存在する場合は、現像に先立ち、支持体を除去する。現像は、アルカリ性水溶液、水系現像液、有機溶剤等の現像液によるウエット現像、ドライ現像等で未露光部を除去することにより行われる。本発明においては、アルカリ性水溶液を用いることが好ましい。アルカリ性水溶液としては、例えば、０．１〜５質量％炭酸ナトリウムの希薄溶液、０．１〜５質量％炭酸カリウムの希薄溶液、０．１〜５質量％水酸化ナトリウムの希薄溶液等が挙げられる。このアルカリ性水溶液のｐＨは９〜１１の範囲とすることが好ましく、その温度は、感光性樹脂組成物層の現像性に合わせて調節される。また、アルカリ性水溶液中には、界面活性剤、消泡剤、有機溶剤等を混入させてもよい。上記現像の方式としては、たとえば、ディップ方式、スプレー方式、ブラッシング、スラッピング等が挙げられる。 A photocured material pattern is formed on the substrate for an image display device by selectively removing the photosensitive resin composition layer in the unexposed portion after the exposure by development. In the development step, when a support is present, the support is removed prior to development. Development is performed by removing unexposed portions by wet development, dry development, or the like using a developer such as an alkaline aqueous solution, an aqueous developer, or an organic solvent. In the present invention, it is preferable to use an alkaline aqueous solution. Examples of the alkaline aqueous solution include a dilute solution of 0.1 to 5 mass% sodium carbonate, a dilute solution of 0.1 to 5 mass% potassium carbonate, a dilute solution of 0.1 to 5 mass% sodium hydroxide, and the like. . The pH of the alkaline aqueous solution is preferably in the range of 9 to 11, and the temperature is adjusted according to the developability of the photosensitive resin composition layer. Moreover, you may mix surfactant, an antifoamer, an organic solvent, etc. in alkaline aqueous solution. Examples of the development method include a dip method, a spray method, brushing, and slapping.
現像後の処理として、形成された前記光硬化物パターンを、必要に応じて６０〜２５０℃程度の加熱処理によりさらに硬化してもよい。 As a treatment after development, the formed photocured product pattern may be further cured by a heat treatment at about 60 to 250 ° C., if necessary.
本発明の画像表示装置の製造方法は、粒子等の表示媒体を前記工程で得た隔壁内に充填する工程と、一方の基板に対向するように隔壁の反対側に基板を貼り付ける工程と、を有する。前記基板としては、ガラス基板若しくはポリマー基板のような絶縁基板又はシリコン基板などの半導体基板若しくはＩＴＯのような電極が形成された半導体基板が挙げられる。 The method for producing an image display device of the present invention includes a step of filling a display medium such as particles in the partition obtained in the above step, a step of attaching a substrate to the opposite side of the partition so as to face one substrate, Have Examples of the substrate include an insulating substrate such as a glass substrate or a polymer substrate, a semiconductor substrate such as a silicon substrate, or a semiconductor substrate on which an electrode such as ITO is formed.
以下に、実施例により本発明をさらに具体的に説明するが、本発明の技術思想を逸脱しない限り、本発明はこれらの実施例に制限されるものではない。 Hereinafter, the present invention will be described more specifically by way of examples. However, the present invention is not limited to these examples without departing from the technical idea of the present invention.
（実施例１〜２及び比較例１〜３）
実施例１、２及び比較例１、２には、表１に示したように下記の樹脂Ａを用い、比較例３には下記の樹脂Ｂを用いた。
樹脂Ａ：メタクリル酸／メタクリル酸メチル／メタクリル酸ブチル共重合体（質量比３０／３５／３５、重量平均分子量５万）の４８質量％メチルセロソルブ／トルエン（質量比６／４）溶液９３．７５ｇ（固形分４５ｇ）、
樹脂Ｂ：メタクリル酸／メタクリル酸メチル／スチレン／ベンジルメタクリレート共重合体（質量比３０／５／４０／２５、重量平均分子量４．６万）の４７質量％メチルセロソルブ／トルエン（質量比６／４）溶液９５．７４ｇ（固形分４５ｇ）（（Ａ）成分）。
また、（Ｂ）成分の光重合性化合物として、ＨＴ−９０８２−９５（末端にヒドロキシル基を有するポリカーボネート化合物、有機イソシアネート及び２−ヒドロキシエチルアクリレートを反応させて得られた光重合性化合物：重量平均分子量４０００、日立化成工業株式会社製、商品名）６ｇ、ＵＡ−２１ＥＢ（新中村化学工業株式会社、商品名）２３ｇ、ＦＡ−０２３Ｍ（日立化成工業株式会社製、商品名）１０ｇ、ＦＡ−０２４Ｍ（日立化成工業株式会社製、商品名）６ｇ、ＦＡ−ＭＥＣＨ（γ−クロロ−β−ヒドロキシプロピル−β’−メタクリロイルオキシエチル−ｏ−フタレート、日立化成工業株式会社製、商品名）１０ｇを用い、
（Ｃ）成分の光重合開始剤として、ＥＡＢ（Ｎ，Ｎ’−テトラエチル−４，４’−ジアミノベンゾフェノン、保土ヶ谷化学工業株式会社製、商品名）０．０５ｇ、ＴＰＳ（トリブロモメチルフェニルスルホン、住友精化株式会社製、製品名）０．５ｇを用い、
（Ｄ）成分の黒色顔料として、ＢＴ−１ＨＣＡ（チタンブラック分散液、株式会社ジェムコ製、商品名）１．２ｇ（（Ｄ）成分）を用い、更にシランカップリング剤、溶剤のＳＺ−６０３０（メタクリロイルオキシプロピルトリメトキシシランシラン、東レ・ダウコーニング株式会社製、商品名）５ｇ、トルエン１２ｇ、メタノール４ｇを配合し、溶液を得た。
(Examples 1-2 and Comparative Examples 1-3)
In Examples 1 and 2 and Comparative Examples 1 and 2, the following resin A was used as shown in Table 1, and in Comparative Example 3, the following resin B was used.
Resin A: 93.75 g of 48% by weight methyl cellosolve / toluene (mass ratio 6/4) solution of methacrylic acid / methyl methacrylate / butyl methacrylate copolymer (mass ratio 30/35/35, weight average molecular weight 50,000) (Solid content 45 g),
Resin B: 47% by mass methyl cellosolve / toluene (mass ratio 6/4) of methacrylic acid / methyl methacrylate / styrene / benzyl methacrylate copolymer (mass ratio 30/5/40/25, weight average molecular weight 46,000) ) Solution 95.74 g (solid content 45 g) (component (A)).
In addition, as the photopolymerizable compound of component (B), HT-9082-95 (photopolymerizable compound obtained by reacting a polycarbonate compound having a hydroxyl group at the terminal, organic isocyanate and 2-hydroxyethyl acrylate: weight average) Molecular weight 4000, manufactured by Hitachi Chemical Co., Ltd., trade name) 6g, UA-21EB (Shin Nakamura Chemical Co., Ltd., trade name) 23g, FA-023M (trade name, manufactured by Hitachi Chemical Co., Ltd.) 10g, FA-024M (Product name, Hitachi Chemical Co., Ltd., 6 g), FA-MECH (γ-chloro-β-hydroxypropyl-β′-methacryloyloxyethyl-o-phthalate, Hitachi Chemical Co., Ltd., product name) 10 g were used. ,
As a photopolymerization initiator of component (C), EAB (N, N′-tetraethyl-4,4′-diaminobenzophenone, Hodogaya Chemical Co., Ltd., trade name) 0.05 g, TPS (tribromomethylphenylsulfone, Sumitomo Seika Co., Ltd., product name) 0.5g,
As a black pigment of component (D), BT-1HCA (titanium black dispersion, manufactured by Gemco Co., Ltd., trade name) 1.2 g (component (D)) was used, and a silane coupling agent and a solvent SZ-6030 ( Methacryloyloxypropyltrimethoxysilanesilane, manufactured by Toray Dow Corning Co., Ltd., trade name) 5 g, toluene 12 g, and methanol 4 g were blended to obtain a solution.
この溶液に表１に示した（Ｃ）成分を溶解させて感光性樹脂組成物を得た。次いで、この感光性樹脂組成物溶液を１６μｍ厚のポリエチレンテレフタレートフィルム（帝人デュポンフィルム株式会社製、商品名：ＨＴＲ−０２）上に均一に塗布し、９０℃の熱風対流式乾燥機で１０分間乾燥した後、ポリエチレン製保護フィルム（フィルム長手方向の引張強さ：１６ＭＰａ、フィルム幅方向の引張強さ：１２ＭＰａ、商品名：ＮＦ−１５，タマポリ株式会社製）で保護して感光性エレメントを得た。感光性樹脂組成物層の乾燥後の膜厚は、４５μｍであった。得られた感光性エレメントについて、塗膜外観を評価した。 The component (C) shown in Table 1 was dissolved in this solution to obtain a photosensitive resin composition. Next, this photosensitive resin composition solution was uniformly applied onto a 16 μm-thick polyethylene terephthalate film (trade name: HTR-02, manufactured by Teijin DuPont Films Ltd.) and dried for 10 minutes with a hot air convection dryer at 90 ° C. The film was protected with a polyethylene protective film (tensile strength in the film longitudinal direction: 16 MPa, tensile strength in the film width direction: 12 MPa, trade name: NF-15, manufactured by Tamapoly Co., Ltd.) to obtain a photosensitive element. . The film thickness after drying of the photosensitive resin composition layer was 45 μm. About the obtained photosensitive element, the coating-film external appearance was evaluated.
一方、ＩＴＯ付ＰＥＴ基材（東洋紡績株式会社製）のＩＴＯ面上に、上記感光性エレメントを、感光性樹脂組成物層がＩＴＯ付ＰＥＴ基材表面に接するように、ポリエチレン製保護フィルムを剥離しながら１１０℃に加熱したラミネートロールを通してラミネートした。できあがった積層物の構成は、下からＩＴＯ付ＰＥＴ基材、感光性樹脂組成物層、ポリエチレンテレフタレートフィルムとなる。得られた積層物について、感度、密着性、解像度および表示特性の評価を行った。 On the other hand, on the ITO surface of the ITO-coated PET substrate (Toyobo Co., Ltd.), the above-mentioned photosensitive element is peeled off so that the photosensitive resin composition layer is in contact with the ITO-coated PET substrate surface. Then, the film was laminated through a laminating roll heated to 110 ° C. The structure of the completed laminate is, from below, a PET substrate with ITO, a photosensitive resin composition layer, and a polyethylene terephthalate film. The obtained laminate was evaluated for sensitivity, adhesion, resolution, and display characteristics.
＜感度の評価＞
高圧水銀灯ランプを有する平行光露光機（株式会社オーク製作所製）ＥＸＭ−１２０１を用いて、４１段ステップタブレットを有するフォトツールを積層物のポリエチレンテレフタレートフィルム上に密着させ、露光を行った。露光後、ポリエチレンテレフタレートフィルムを剥離し、１質量％炭酸ナトリウム水溶液を３０℃で２０秒間スプレーすることにより、未露光部分を除去した。４１段ステップタブレットの現像後の残存ステップ段数が２９．０となるエネルギー量を感度（ｍＪ／ｃｍ２）とした。このエネルギー量の数値が小さい程、感度が高いことを示す。表１に評価結果を示した。
<Evaluation of sensitivity>
Using a parallel light exposure machine (manufactured by Oak Manufacturing Co., Ltd.) EXM-1201 having a high-pressure mercury lamp, a phototool having a 41-step tablet was brought into close contact with the laminated polyethylene terephthalate film for exposure. After the exposure, the polyethylene terephthalate film was peeled off, and a 1% by mass aqueous sodium carbonate solution was sprayed at 30 ° C. for 20 seconds to remove unexposed portions. The amount of energy at which the number of steps remaining after development of the 41-step tablet was 29.0 was defined as sensitivity (mJ / cm 2 ). It shows that a sensitivity is so high that the numerical value of this energy amount is small. Table 1 shows the evaluation results.
＜密着性の評価＞
高圧水銀灯ランプを有する平行光露光機（株式会社オーク製作所製）ＥＸＭ−１２０１を用いて、密着性評価用ネガとしてライン幅／スペース幅が１０／３００〜８０／３００（単位：μｍ、スペース幅一定）の配線パターンを有するフォトツールと、４１段ステップタブレットを有するフォトツールを積層物のポリエチレンテレフタレートフィルム上に密着させ、４１段ステップタブレットの現像後の残存ステップ段数が２９．０となるエネルギー量で露光を行った。露光後、ポリエチレンテレフタレートフィルムを剥離し、１質量％炭酸ナトリウム水溶液を３０℃で２０秒間スプレーすることにより、未露光部分を除去して密着性を評価した。密着性は現像液により剥離されずに残ったラインの幅（μｍ）で表され、この数値が小さい程、細いラインでもガラス基板から剥離せずに密着していることから、密着性が高いことを示す。表１に評価結果を示した。
<Evaluation of adhesion>
Using a parallel light exposure machine (manufactured by Oak Manufacturing Co., Ltd.) EXM-1201 having a high-pressure mercury lamp, the line width / space width is 10/300 to 80/300 (unit: μm, space width constant) as a negative for adhesion evaluation ) And a phototool having a 41-step tablet are closely attached to the polyethylene terephthalate film of the laminate, and the amount of energy of the remaining step after development of the 41-step tablet is 29.0. Exposure was performed. After the exposure, the polyethylene terephthalate film was peeled off, and a 1% by mass sodium carbonate aqueous solution was sprayed at 30 ° C. for 20 seconds to remove the unexposed portion and evaluate the adhesion. Adhesiveness is expressed by the width (μm) of the line that remains without being peeled off by the developer. The smaller the value, the higher the adhesiveness because the thin line is in close contact with the glass substrate without being peeled off. Indicates. Table 1 shows the evaluation results.
＜解像度の評価＞
４１段ステップタブレットを有するフォトツールと、解像度評価用ネガとしてライン幅／スペース幅が３０／３０〜２００／２００（単位：μｍ）の配線パターンを有するフォトツールを積層物のポリエチレンテレフタレートフィルム上に密着させ、高圧水銀灯ランプを有する平行光露光機（株式会社オーク製作所製）ＥＸＭ−１２０１を用いて、４１段ステップタブレットの現像後の残存ステップ段数が２９．０となるエネルギー量で露光を行った。露光後、ポリエチレンテレフタレートフィルムを剥離し、１質量％炭酸ナトリウム水溶液を３０℃で２０秒間スプレーすることにより、未露光部分を除去して解像度を評価した。解像度は現像処理によって未露光部が良好に除去された最も小さいスペース幅（μｍ）で表され、この数値が小さいほど解像度は良好である。表１に評価結果を示した。
<Evaluation of resolution>
A phototool having a 41-step tablet and a phototool having a wiring pattern with a line width / space width of 30/30 to 200/200 (unit: μm) as a negative for resolution evaluation are closely attached to a polyethylene terephthalate film of a laminate. Then, using a parallel light exposure machine (manufactured by Oak Manufacturing Co., Ltd.) EXM-1201 having a high-pressure mercury lamp lamp, exposure was performed with an energy amount such that the number of remaining step stages after development of the 41-step step tablet was 29.0. After the exposure, the polyethylene terephthalate film was peeled off, and a 1% by mass aqueous sodium carbonate solution was sprayed at 30 ° C. for 20 seconds to remove unexposed portions and evaluate the resolution. The resolution is represented by the smallest space width (μm) in which the unexposed portion is well removed by the development processing, and the smaller the numerical value, the better the resolution. Table 1 shows the evaluation results.
＜表示特性の評価＞
高圧水銀灯ランプを有する平行光露光機（株式会社オーク製作所製）ＥＸＭ−１２０１を用いて、密着性評価用ネガとしてライン幅／スペース幅が２０／３００（単位：μｍ、）の配線パターンを有するフォトツールと、４１段ステップタブレットを有するフォトツールを積層物のポリエチレンテレフタレートフィルム上に密着させ、４１段ステップタブレットの現像後の残存ステップ段数が２９．０となるエネルギー量で露光を行った。露光後、ポリエチレンテレフタレートフィルムを剥離し、１質量％炭酸ナトリウム水溶液を３０℃で２０秒間スプレーすることにより、未露光部分を除去して隔壁を形成した。表示媒体を前記工程で得た隔壁内に充填し、一方の基板に対向するように隔壁の反対側にＩＴＯ付ＰＥＴ基板を貼り付けることによりテストパターンを形成した。
上記テストパターンに電場をかけ、表示媒体を移動させ、一定時間放置し、また電場をかけ表示媒体を再度移動させる。これを何万回か繰り返し、コントラストが劣化しないか検討した。コントラストの劣化が見られないものを「○」、劣化が見られたものを「×」として評価した。表１に評価結果を示した。
<Evaluation of display characteristics>
Photo having a wiring pattern with a line width / space width of 20/300 (unit: μm) as a negative for adhesion evaluation using a parallel light exposure machine (manufactured by Oak Manufacturing Co., Ltd.) EXM-1201 having a high-pressure mercury lamp. The tool and a phototool having a 41-step tablet were brought into close contact with the polyethylene terephthalate film of the laminate, and the exposure was performed with an energy amount of 29.0 after development of the 41-step tablet. After the exposure, the polyethylene terephthalate film was peeled off, and a 1% by mass aqueous sodium carbonate solution was sprayed at 30 ° C. for 20 seconds to remove unexposed portions and form partition walls. The display medium was filled in the partition walls obtained in the above step, and a test pattern was formed by attaching a PET substrate with ITO on the opposite side of the partition walls so as to face one substrate.
An electric field is applied to the test pattern, the display medium is moved, left for a certain period of time, and the electric field is applied to move the display medium again. This was repeated tens of thousands of times to examine whether the contrast deteriorated. The case where no deterioration of contrast was observed was evaluated as “◯”, and the case where deterioration was observed was evaluated as “×”. Table 1 shows the evaluation results.
＊２ Ｉ−６５１；ベンジルジメチルケタール（チバスペシャリティーケミカル社製、商品名）
* 2 I-651; benzyl dimethyl ketal (trade name, manufactured by Ciba Specialty Chemicals)
本発明の画像表示装置の隔壁を形成するための感光性樹脂組成物は、（Ａ）バインダーポリマーとして（メタ）アクリル酸ブチルと（メタ）アクリル酸を単量体成分として必須に含有し、さらに、（Ｃ）光重合開始剤として、一般式（Ｉ）と一般式（ＩＩ）で表わされる化合物の少なくとも２種類を併用して用いる。
（メタ）アクリル酸ブチルを単量体成分として含有しない樹脂Ｂを用いた比較例３は、表示特性に劣り、光重合開始剤の一般式（Ｉ）と一般式（ＩＩ）で表される光重合開始剤の一方のみ用いた比較例１、２は、感度が低く、解像度にも劣る。
これに対し、本発明の（メタ）アクリル酸ブチルと（メタ）アクリル酸を必須の単量体成分として含有するバインダーと、２種類の光重合開始剤を用いた実施例１、２では、感度、解像度、密着性が良好で、表示特性にも優れる。
The photosensitive resin composition for forming the partition walls of the image display device of the present invention essentially contains (A) butyl (meth) acrylate and (meth) acrylic acid as monomer components as a binder polymer, and (C) As the photopolymerization initiator, at least two kinds of compounds represented by the general formula (I) and the general formula (II) are used in combination.
The comparative example 3 using the resin B which does not contain (meth) butyl acrylate as a monomer component is inferior in display characteristics, and is represented by the general formulas (I) and (II) of the photopolymerization initiator. Comparative Examples 1 and 2 using only one of the polymerization initiators have low sensitivity and poor resolution.
On the other hand, in Examples 1 and 2 using a binder containing butyl (meth) acrylate and (meth) acrylic acid as essential monomer components of the present invention and two types of photopolymerization initiators, , Good resolution and adhesion, and excellent display characteristics.
Claims (8)
前記感光性樹脂組成物が、（Ａ）（メタ）アクリル酸ブチル及び（メタ）アクリル酸を単量体単位として有するバインダーポリマー、（Ｂ）光重合性化合物、（Ｃ）光重合開始剤、（Ｄ）黒色顔料を含み、
前記（Ｃ）光重合開始剤が、下記一般式（Ｉ）で表わされる化合物、及び下記一般式（ＩＩ）で表わされる化合物を含有する感光性樹脂組成物。
The photosensitive resin composition comprises (A) a binder polymer having butyl (meth) acrylate and (meth) acrylic acid as monomer units, (B) a photopolymerizable compound, (C) a photopolymerization initiator, D) containing a black pigment,
The photosensitive resin composition in which the (C) photopolymerization initiator contains a compound represented by the following general formula (I) and a compound represented by the following general formula (II).
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| JP5920357B2 (en) * | 2011-11-01 | 2016-05-18 | 日立化成株式会社 | Photosensitive resin composition, photosensitive element using the same, cured product, method for forming partition wall of image display device, method for manufacturing image display device, and image display device |
| JP2015143809A (en) * | 2013-12-25 | 2015-08-06 | 日立化成株式会社 | Photosensitive resin composition, photosensitive element, method for forming resist pattern, and method for manufacturing printed wiring board |
| JP6390143B2 (en) * | 2014-04-08 | 2018-09-19 | 東洋インキＳｃホールディングス株式会社 | Black composition, black coating film, and laminate |
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| JPH0635190A (en) * | 1992-07-15 | 1994-02-10 | Asahi Denka Kogyo Kk | Photosensitive resin composition and laminated body using same |
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