JP2010084119A5

JP2010084119A5 -

Info

Publication number: JP2010084119A5
Application number: JP2009052082A
Authority: JP
Filing date: 2009-03-05
Publication date: 2011-10-20
Anticipated expiration: 2029-03-05

Description

前記課題を解決するための手段は以下の通りである。
＜１＞塩基性窒素原子を有する高分子化合物で顔料を被覆してなる加工顔料。
＜２＞前記塩基性窒素原子を有する高分子化合物が、下記（１）〜（４）から選択されるから選択される少なくとも１種の高分子化合物である＜１＞に記載の加工顔料。
（１）炭素数２〜６のアルキレン基を有するポリ（アルキレンイミン）
（２）ポリアリルアミン
（３）ポリビニルアミン
（４）エステル部に塩基性窒素原子を有する（メタ）アクリル酸エステル、ビニルピリジン、及びアミノスチレンから選択される１種以上のモノマー成分を有する高分子化合物
＜３＞平均１次粒子径が５ｎｍ〜２５ｎｍの範囲である＜１＞又は＜２＞に記載の加工顔料。
＜４＞前記顔料が、ポリハロゲン化亜鉛フタロシアニンを含む顔料である＜１＞〜＜３＞のいずれか１項に記載の加工顔料。
＜５＞前記塩基性窒素原子を有する高分子化合物が、数平均分子量５００〜１，０００，０００であるオリゴマー鎖又はポリマー鎖を側鎖に有する＜１＞〜＜４＞のいずれか１項に記載の加工顔料。
＜６＞前記塩基性窒素原子を有する高分子化合物に含まれるオリゴマー鎖又はポリマー鎖が、ポリカプロラクトンである＜５＞に記載の加工顔料。
＜７＞＜１＞〜＜６＞のいずれか１項に記載の加工顔料を、有機溶剤中に分散してなる顔料分散組成物。
＜８＞更に、顔料分散剤を含む＜７＞に記載の顔料分散組成物。
＜９＞＜７＞又は＜８＞に記載の顔料分散組成物と、重合性化合物と、光重合開始剤と、を含有する光硬化性組成物。
＜１０＞＜９＞に記載の光硬化性組成物を用いて形成された着色領域を有するカラーフィルタ。
＜１１＞＜９＞に記載の光硬化性組成物を直接又は他の層を介して基板上に付与して感光性膜を形成する工程と、前記形成された感光性膜にパターン露光及び現像を順次行なうことにより着色領域を形成する工程と、を含むことを特徴とするカラーフィルタの製造方法。 Means for solving the above-mentioned problems are as follows.
<1> A processed pigment obtained by coating a pigment with a polymer compound having a basic nitrogen atom.
<2> The processed pigment according to <1>, wherein the polymer compound having a basic nitrogen atom is at least one polymer compound selected from the following (1) to (4).
(1) Poly (alkyleneimine) having an alkylene group having 2 to 6 carbon atoms
(2) Polyallylamine (3) Polyvinylamine (4) Polymer compound having one or more monomer components selected from (meth) acrylic acid ester having a basic nitrogen atom in the ester part, vinylpyridine, and aminostyrene <3> The processed pigment according to <1> or <2>, wherein the average primary particle diameter is in the range of 5 nm to 25 nm.
<4> The processed pigment according to any one of <1> to <3>, wherein the pigment is a pigment containing polyhalogenated zinc phthalocyanine.
<5> In any one of <1> to <4>, the polymer compound having a basic nitrogen atom has an oligomer chain or a polymer chain having a number average molecular weight of 500 to 1,000,000 in a side chain. The described processed pigment.
<6> The processed pigment according to < 5 >, wherein the oligomer chain or polymer chain contained in the polymer compound having a basic nitrogen atom is polycaprolactone.
<7> A pigment dispersion composition obtained by dispersing the processed pigment according to any one of <1> to <6> in an organic solvent.
<8> The pigment dispersion composition according to <7>, further comprising a pigment dispersant.
<9> A photocurable composition comprising the pigment dispersion composition according to <7> or <8>, a polymerizable compound, and a photopolymerization initiator.
<10> A color filter having a colored region formed using the photocurable composition according to < 9 >.
<11> A step of applying the photocurable composition according to <9> directly or via another layer onto a substrate to form a photosensitive film, and pattern exposure and development on the formed photosensitive film Forming a colored region by sequentially performing the steps described above.

本発明の加工顔料の他の好ましい態様は以下の通りである。
＜１２＞１−メトキシ−２−プロパノールで洗浄したときの塩基性窒素原子を有する高分子化合物の遊離量が３０質量％以下である＜１＞〜＜６＞のいずれかに記載の加工顔料。
＜１３＞前記塩基性窒素原子を有する高分子化合物を、顔料の微細化工程で添加して製造したことを特徴とする＜１＞〜＜６＞、及び＜１２＞のいずれか１項に記載の加工顔料。
＜１４＞前記塩基性窒素原子を有する高分子化合物の重量平均分子量が、１，０００〜１００，０００の範囲であることを特徴とする＜１＞〜＜６＞、＜１２＞及び＜１３＞のいずれか１項に記載の加工顔料。 Other preferred embodiments of the processed pigment of the present invention are as follows.
<12> The processed pigment according to any one of <1> to <6>, wherein a liberated amount of the polymer compound having a basic nitrogen atom when washed with 1-methoxy-2-propanol is 30% by mass or less.
<13>, wherein the polymer compound having a basic nitrogen atom, and added pigment micronization step is characterized in that produced <1> to <6>, and any one of <12> Processed pigments.
<14> The polymer compound having a basic nitrogen atom has a weight average molecular weight in the range of 1,000 to 100,000. <1> to <6>, <1 2 > and <1 processed pigment according to any one of 3>.

さらに、顔料としてポリハロゲン化亜鉛フタロシアニンを適用した本発明の加工顔料を含む顔料分散組成物は、その優れた分散性及び分散安定性は保持されたままに、該顔料分散組成物を含む光硬化性組成物を用いてカラーフィルタを作製した際には、輝度及びコントラストにより優れたカラーフィルタを得ることができる。 Furthermore, the pigment dispersion composition containing the processed pigment of the present invention in which polyhalogenated zinc phthalocyanine is applied as a pigment is a photocurable composition containing the pigment dispersion composition while maintaining its excellent dispersibility and dispersion stability. with sexual composition in the case of preparing a color filter can be obtained an excellent color filter by the brightness and contrast.

＜グラフト型高分子＞
特定高分子化合物が、グラフト型高分子である場合、該高分子化合物としては、数平均分子量５００〜１，０００，０００であるオリゴマー鎖又はポリマー鎖を側鎖に有するものであることが好ましい。また、該オリゴマー鎖又はポリマー鎖としては、良好な分散性を得られるという観点から、ポリカプロラクトンであることが好ましい。
オリゴマー鎖又はポリマー鎖の数平均分子量はＧＰＣ法によるポリスチレン換算値により測定することができる。 <Graft polymer>
When the specific polymer compound is a graft polymer, the polymer compound preferably has an oligomer chain or a polymer chain having a number average molecular weight of 500 to 1,000,000 in the side chain . Also, examples of the oligomer chain or polymer chain, from the viewpoint of obtaining favorable dispersibility is preferably polycaprolactone.
The number average molecular weight of the oligomer chain or polymer chain can be measured by a polystyrene conversion value by GPC method.

＜Ｂ５．光硬化性組成物によるカラーフィルタの作製及び評価＞
（１）パターン形成性の評価
上記のように調製した光硬化性組成物を、前記Ｂ２．で得られた下塗り層付シリコンウエハの下塗り層上に塗布し、着色層（塗布膜）を形成した。そして、この塗布膜の乾燥膜厚が０．５μｍになるように、１００℃のホットプレートを用いて１２０秒間加熱処理（プリベーク）を行なった。
次いで、ｉ線ステッパー露光装置ＦＰＡ−３０００ｉ５＋（Ｃａｎｏｎ（株）製）を使用して３６５ｎｍの波長でパターンが２μｍ四方のＩｓｌａｎｄパターンマスクを通して５０〜１２００ｍＪ／ｃｍ^２の種々の露光量で露光した。
その後、照射された塗布膜が形成されているシリコンウエハ基板をスピン・シャワー現像機（ＤＷ−３０型、（株）ケミトロニクス製）の水平回転テーブル上に載置し、ＣＤ−２０００（富士フイルムエレクトロニクスマテリアルズ（株）製）を用いて２３℃で６０秒間パドル現像を行ない、シリコンウエハ基板に着色パターンを形成した。 <B5. Production and Evaluation of Color Filter with Photocurable Composition>
(1) Evaluation of pattern formation property The photocurable composition prepared as described above was prepared using the B2. The colored layer (coating film) was formed by coating on the undercoat layer of the silicon wafer with the undercoat layer obtained in (1). Then, heat treatment (pre-baking) was performed for 120 seconds using a hot plate at 100 ° C. so that the dry film thickness of the coating film became 0.5 μm.
Next, using an i-line stepper exposure apparatus FPA-3000i5 + (manufactured by Canon Inc.), exposure was performed at various exposure doses of 50 to 1200 mJ / cm ² through an Island pattern mask having a pattern of 2 μm square at a wavelength of 365 nm.
Thereafter, irradiated coated film silicon is formed upper blade board spin-shower developing machine (DW-30 type, Ltd. Chemitronics) was mounted on a horizontal rotary table of, CD-2000 ( FUJIFILM electronic performs Materials Co., Ltd.) for 60 seconds and puddle developed at 23 ° C. was used to form a colored pattern on the silicon wafer wafer board.

着色パターンが形成されたシリコンウエハを真空チャック方式で前記水平回転テーブルに固定し、回転装置によって該シリコンウエハ基板を回転数５０ｒ．ｐ．ｍ．で回転させつつ、その回転中心の上方より純水を噴出ノズルからシャワー状に供給してリンス処理を行ない、その後スプレー乾燥した。
パターン形成性は、以上のようにして形成された着色パターンの断面形状を観察することにより評価した。パターン断面形状は矩形が好ましく、逆テーパーは好ましくない。
結果を表７に示す。 The silicon wafer on which the colored pattern was formed was fixed to the horizontal rotary table by a vacuum chuck method, the rotational speed 50r the silicon wafer wafer board by a rotary device. p. m. While being rotated, pure water was supplied from the upper part of the rotation center in the form of a shower through a spray nozzle, followed by rinsing treatment, and then spray drying.
The pattern formability was evaluated by observing the cross-sectional shape of the colored pattern formed as described above. The pattern cross-sectional shape is preferably rectangular, and reverse taper is not preferable.
The results are shown in Table 7.

Claims

A processed pigment obtained by coating a pigment with a polymer compound having a basic nitrogen atom.

The processed pigment according to claim 1, wherein the polymer compound having a basic nitrogen atom is at least one polymer compound selected from the following (1) to (4).
(1) Poly (alkyleneimine) having an alkylene group having 2 to 6 carbon atoms
(2) Polyallylamine (3) Polyvinylamine (4) A structural unit derived from one or more monomers selected from (meth) acrylic acid ester having a basic nitrogen atom in the ester part, vinylpyridine, and aminostyrene Including polymer compounds

The processed pigment according to claim 1 or 2, wherein the average primary particle diameter is in the range of 5 nm to 25 nm.

The processed pigment according to any one of claims 1 to 3, wherein the pigment is a pigment containing polyhalogenated zinc phthalocyanine.

The processing according to any one of claims 1 to 4, wherein the polymer compound having a basic nitrogen atom has an oligomer chain or a polymer chain having a number average molecular weight of 500 to 1,000,000 in a side chain. Pigments.

The processed pigment according to claim 5 , wherein the oligomer chain or polymer chain contained in the polymer compound having a basic nitrogen atom is polycaprolactone.

The pigment dispersion composition formed by disperse | distributing the processed pigment of any one of Claims 1-6 in the organic solvent.

The pigment dispersion composition according to claim 7, further comprising a pigment dispersant.

The photocurable composition containing the pigment dispersion composition of Claim 7 or Claim 8, a polymeric compound, and a photoinitiator.

A color filter having a colored region formed using the photocurable composition according to claim 9.

A step of forming a photosensitive film by applying the photocurable composition according to claim 9 directly or through another layer to a photosensitive film, and sequentially performing pattern exposure and development on the formed photosensitive film. And a step of forming a colored region.