JP3709112B2 - Pigment dispersion for color filter, method for producing color filter, and color filter - Google Patents

Description

（但し、上記式中のＸは、水酸基、アルコキシ基、１〜３級アミノ基又はアシルアミノ基であり、Ｙは４位に水素原子、水酸基、アルコキシ基、１〜３級アミノ基又はアシルアミノ基を有するアントラキノニルアミノ基、フェニルアミノ基或いはフェノキシ基であり、Ａ及びＢはアルキル基、シクロアルキル基又はアリール基であり、Ａ又はＢの少なくとも一方は塩基性窒素原子を有する置換基を少なくとも１個有し、Ｚは水素原子、シアノ基、ハロゲン原子、アルキル基、アルコキシ基、ニトロ基、ベンゾイルアミノ基又はベンゾイル基（３位）を表わし、該ベンゾイル基はＸと結合してアクリドン環を形成してもよい。）
上記「塩基性窒素原子を有する置換基」とは、１級、２級又は３級アミノ基、第４級アンモニウム基及び／又はピリジニウム基であり、特に３級アミノ基が好ましい。
【０００９】
本発明のＣＦ用顔料分散液は、トリアジニルアミノアントラキノン系色素の特定の誘導体を、顔料の分散剤として使用したことが特徴であり、該分散剤の使用によりＣＦ用顔料分散液の顔料粒子の凝集が防止される。その結果、ＣＦ用顔料分散液は構造粘性が低減され、低粘度で、顔料分散液の増粘ゲル化が抑制され、貯蔵安定性も増加する。又、前記一般式（Ｉ）で表わされる分散剤は、それ自体黄味赤〜青味赤の色調を有しており、この分散剤を、青色顔料とその補色顔料である紫色顔料、及び赤色顔料とその補色顔料である黄色顔料の分散剤としてそれぞれ使用し、得られた顔料分散液を、液晶ディスプレイ等のＣＦの画素形成に用いた場合に望ましい色品位の画素を形成することができる。
【００１０】
【発明の実施の形態】
次に好ましい実施の形態を挙げて本発明を詳細に説明する。
本発明で使用する前記の一般式（Ｉ）で表わされる分散剤は、例えば、特公昭４６−３３２３２号公報、特公昭４６−３３２３３号及び特公昭４６−３４５１８号公報に開示されている製造方法或いはそれに準じる方法で製造される。１例を挙げれば、１−アミノ−４−ベンゾイルアミノアントラキノン１モルとアニリン又はフェノール１モルと塩化シアヌル１モルとをｏ−ジクロロベンゼン等の不活性な溶媒中で１３０℃〜１６０℃で２〜６時間、更に少なくとも１個の２級アミノ基と少なくとも１個の３級アミノ基を有し且つ１級アミノ基を有さないポリアミン１モルを添加して１５０〜１７０℃で３〜４時間の反応条件で反応させることによって得られる。
【００１１】
上記方法において使用する「少なくとも１個の２級アミノ基と少なくとも１個の３級アミノ基を有し、且つ１級アミノ基を有さないポリアミン」としては、例えば、
Ｎ，Ｎ，Ｎ′−トリメチル−エチレンジアミン
Ｎ，Ｎ−ジメチル−Ｎ′−エチル−エチレンジアミン
Ｎ，Ｎ−ジエチル−Ｎ′−メチル−エチレンジアミン
Ｎ，Ｎ−ジメチル−Ｎ′−エチル−プロピレンジアミン
Ｎ，Ｎ，Ｎ′−トリメチル−プロピレンジアミン
Ｎ，Ｎ，Ｎ′−トリエチル−プロピレンジアミン
Ｎ，Ｎ，Ｎ′−トリメチル−ヘキサメチレンジアミン
Ｎ，Ｎ−ジエチル−Ｎ′−メチル−ｐ−フェニレンジアミン
Ｎ，Ｎ−ジプロピル−Ｎ′−メチル−ｐ−フェニレンジアミン
Ｎ，Ｎ，Ｎ′−トリメチル−ｐ−フェニレンジアミン
Ｎ，Ｎ，Ｎ′−トリメチル−ｍ−フェニレンジアミン
Ｎ，Ｎ，Ｎ′−トリエチル−ｐ−フェニレンジアミン
Ｎ，Ｎ−ジエチル−Ｎ′−メチル−１，４−ジアミノシクロヘキサン
Ｎ，Ｎ−ジエチル−Ｎ′−メチル−１，３−ジアミノシクロヘキサン
Ｎ，Ｎ，Ｎ′−トリメチル−１，４−ジアミノシクロヘキサン
Ｎ，Ｎ，Ｎ′−トリエチル−１，４−ジアミノシクロヘキサン
Ｎ−メチルピペラジン
Ｎ−エチルピペラジン
Ｎ−イソブチルピペラジン
２−クロロフェニルピペラジン
Ｎ−（２−ピリジル）ピペラジン
Ｎ−（４−ピリジル）ピペラジン
メチルホモピペラジン等が挙げられる。
【００１２】
上記化合物に加えて、特に好ましいものとしては、
Ｎ，Ｎ，Ｎ″，Ｎ″−テトラメチルジエチレントリアミン
Ｎ，Ｎ，Ｎ″，Ｎ″−テトラ（ｎ−プロピル）ジエチレントリアミン
Ｎ，Ｎ，Ｎ″，Ｎ″−テトラ（ｉ−プロピル）ジエチレントリアミン
Ｎ，Ｎ，Ｎ″，Ｎ″−テトラ（ｎ−ブチル）ジエチレントリアミン
Ｎ，Ｎ，Ｎ″，Ｎ″−テトラ（ｉ−ブチル）ジエチレントリアミン
Ｎ，Ｎ，Ｎ″，Ｎ″−テトラ（ｓ−ブチル）ジエチレントリアミン
Ｎ，Ｎ，Ｎ″，Ｎ″−テトラ（ｔ−ブチル）ジエチレントリアミン
３，３′−イミノビス（Ｎ，Ｎ−ジメチルプロピルアミン）
３，３′−イミノビス（Ｎ，Ｎ−ジエチルプロピルアミン）
３，３′−イミノビス〔Ｎ，Ｎ−ジ（ｎ−プロピル）プロピルアミン〕
３，３′−イミノビス〔Ｎ，Ｎ−ジ（ｉ−プロピル）プロピルアミン〕
３，３′−イミノビス〔Ｎ，Ｎ−ジ（ｎ−ブチル）プロピルアミン〕
３，３′−イミノビス〔Ｎ，Ｎ−ジ（ｉ−ブチル）プロピルアミン〕
３，３′−イミノビス〔Ｎ，Ｎ−ジ（ｓ−ブチル）プロピルアミン〕
３，３′−イミノビス〔Ｎ，Ｎ−ジ（ｔ−ブチル）プロピルアミン〕
４，４′−イミノビス（Ｎ，Ｎ−ジメチルブチルアミン）
４，４′−イミノビス（Ｎ，Ｎ−ジエチルブチルアミン）
２，９−ジメチル−２，５，９−トリアザデカン
２，１２−ジメチル−２，６，１２−トリアザトリデカン
２，１２−ジメチル−２，５，１２−トリアザトリデカン
２，１６−ジメチル−２，９，１６−トリアザヘプタデカン
３−エチル−１０−メチル−３，６，１０−トリアザウンデカン
５，１３−ジ（ｎ−ブチル）−５，９，１３−トリアザヘプタデカン
２，２′−ジピコリルアミン
３，３′−ジピコリルアミン等が挙げられる。
【００１３】
上記方法等により得られる分散剤のうちで本発明において好ましい分散剤は、下記の一般式（１）で表される化合物であり、更に好ましい分散剤は下記の一般式（２）で表される化合物であり、特に好ましい分散剤は下記の一般式（３）で表される化合物である。

（但し、上記式中のＸ、Ｙ及びＺは前記定義の通りであり、Ｒ₁〜Ｒ₄は、同じでも異なってもよく、置換若しくは未置換のアルキル基又は置換若しくは未置換のシクロアルキル基であり、Ｒ₁とＲ₂及び／又はＲ₃とＲ₄は、夫々隣接する窒素原子と結合して更に窒素原子、酸素原子又は硫黄原子を含んでもよい複素環を形成してもよく、Ｒ₅及びＲ₆は、アルキレン基、シクロアルキレン基又はアリーレン基である。）
【００１４】

（但し、上記式中のＸ、Ｙ、Ｚ及びＲ₁〜Ｒ₄は前記定義の通りであり、ｎ及びｍは２〜３０の整数である。）
【００１５】
尚、前記の式（Ｉ）及び上記の式（１）〜（２）におけるアシルアミノ基は、−ＮＨＣＯＲで示される基であり、例えば、Ｒは、フェニル基、メチル基、エチル基、プロピル基、ブチル基等である。

（但し、上記式中のＸはベンゾイルアミノ基であり、Ｚは水素原子であり、Ｒ₁〜Ｒ₄は、同じでも異なってもよく、メチル基又はエチル基を、ｎ及びｍは２又は３を表す。）
【００１６】
本発明において好ましい分散剤の具体例を以下に挙げるが、本発明で使用する分散剤はこれらの例示に限定されるものではない。尚、以下の式中のＸはベンゾイルアミノ基を表わす。

【００１７】

【００１８】

【００１９】

【００２０】

【００２１】

【００２２】

【００２３】

【００２４】

【００２５】

【００２６】

及び上記具体例１〜６及び９〜１１の第４級アンモニウム化合物及び具体例７〜８のピリジニウム化合物。
【００２７】
本発明のＣＦ用顔料分散液は、上記の分散剤と顔料と被膜形成樹脂と液媒体から構成される。本発明のＣＦ用顔料分散液を調製する場合には、上記の分散剤を顔料１００重量部に対して、０．５〜５０重量部、好ましくは１〜３０重量部の割合で使用する。使用量が０．５重量部未満では本発明で使用する分散剤の効果が殆ど認められず、一方、５０重量部より多く使用しても使用する量に見合った効果が得られない。
【００２８】
本発明でＣＦ用顔料分散液に使用される好適な顔料は、例えば、Ｃ．Ｉ．ピグメントレッド（以下Ｐ．Ｒ．と称す）１７７、Ｐ．Ｒ．２５４、Ｐ．Ｒ．２４２、Ｐ．Ｒ．２０９、Ｐ．Ｒ．２２４；Ｃ．Ｉ．ピグメントグリーン（以下Ｐ．Ｇ．と称す）３６、Ｐ．Ｇ．７；Ｃ．Ｉ．ピグメントブルー（以下Ｐ．Ｂ．と称す）１５：６、Ｐ．Ｂ．６０：Ｃ．Ｉ．ピグメントイエロー（以下Ｐ．Ｙ．と称す）１３８、Ｐ．Ｙ．１８５、Ｐ．Ｙ．１５０、Ｐ．Ｙ．１３９、Ｐ．Ｙ．８３：Ｃ．Ｉ．ピグメントバイオレット（以下Ｐ．Ｖ．と称す）２３、Ｃ．Ｉ．ピグメントブラック（以下Ｐ．ＢＬ．と称す）６、Ｐ．ＢＬ．７等が用いられる。又、これらの顔料は、その色相と液晶ディスプレイに要求される色特性の差を補うために適当に混合して使用される場合がある。
【００２９】
本発明のＣＦ用顔料分散液を製造する方法としては、適当な被膜形成樹脂を含む有機溶剤溶液又は水溶液中に顔料と分散剤とを添加してプレミキシングし、その後に顔料を分散処理する。例えば、使用する顔料と分散剤とを横形媒体分散機、縦型媒体分散機、ピンミル、アトライター、ボールミル等の分散機械で均一に混合粉砕し、これを被膜形成樹脂を含む液中に添加混合する方法、水又は有機溶媒中に顔料を均一に懸濁させ、これに分散剤を含有する溶液を添加混合し、顔料粒子表面に分散剤を沈着させたものを被膜形成樹脂を含む液中に添加混合する方法、硫酸等に顔料及び分散剤を溶解した後に、該硫酸溶液を水中に析出させ、両者を固溶体として分離し、これを被膜形成樹脂を含む液中に添加混合する方法等が挙げられる。
【００３０】
本発明において顔料を分散させて顔料分散液にするための被膜形成樹脂を含む液としては、従来公知のＣＦ用顔料分散液に使用される被膜形成樹脂を含む液が用いられる。又、液媒体として有機溶剤、水、有機溶剤と水との混合物が使用され、有機溶剤としては、例えば、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エチルエーテル、エチレングリコールモノメチルエーテルアセテート、エチ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メチルエーテル、プロピレングリコールモノエチルエーテル、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エチルエーテルアセテート、３−メトキシブチルアセテート、シクロヘキサノン、乳酸エチル等が挙げられる。又、必要に応じて従来公知の添加剤、例えば、分散助剤、平滑化剤、密着化剤等の添加剤を顔料分散液に添加することができる。上記の被膜形成樹脂を含む液中の被膜形成樹脂に対する顔料の添加割合は、被膜形成樹脂１００重量部に対し、５重量部〜５００重量部の範囲が好ましい。
【００３１】
被膜形成樹脂を含む液としては、塗布方法や画素パターンの形成方法等により適切に選択し、感光性の被膜形成樹脂を含む液と非感光性被膜形成樹脂を含む液が使用される。感光性被膜形成樹脂を含む液としては、例えば、紫外線硬化性インキ、電子線硬化インキ等に用いられる感光性被膜形成樹脂を含む液が挙げられ、非感光性被膜形成樹脂を含む液としては、例えば、凸版インキ、平版インキ、凹版グラビヤインキ、孔版スクリーンインキ等の印刷インキに使用するワニス、電着塗装に使用するワニス、電子印刷や静電印刷の現像剤に使用するワニス、熱転写リボンに使用するワニス等が挙げられる。
【００３２】
感光性被膜形成樹脂の例としては、感光性環化ゴム系樹脂、感光性フェノール系樹脂、感光性ポリアクリレート系樹脂、感光性ポリアミド系樹脂、感光性ポリイミド系樹脂、不飽和ポリエステル系樹脂、ポリエステルアクリレート系樹脂、ポリエポキシアクリレート系樹脂、ポリウレタンアクリレート系樹脂、ポリエーテルアクリレート系樹脂、ポリオールアクリレート系樹脂等の感光性樹脂が挙げられる。これらの樹脂は単独で或いは２種以上を組み合わせて使用される。上記感光性被膜形成樹脂のなかで好適な樹脂は、分子内にフリーのカルボキシル基を有するアクリレート系のアルカリ現像可能な樹脂が望ましい。これらの感光性被膜形成樹脂を含む液には、更に反応性希釈剤として各種のモノマーを加えることができる。
【００３３】
又、感光性被膜形成樹脂を含む顔料分散液にベンゾインエーテル、ベンゾフェノン等の光重合開始剤を加え、従来公知の方法により練肉することにより、光硬化性の感光性顔料分散液とすることができる。又、上記の光重合開始剤に代えて熱重合開始剤を使用して熱硬化性顔料分散液とすることができる。
上記の感光性顔料分散液を用いてＣＦのパターンを形成する場合には、ガラス等の透明ＣＦ基板上に前記感光性顔料分散液をスピンコーター、低速回転コーター、ロールコーター、ナイフコーター等を用いて全面コーティングを行うか、或いは各種の印刷方法による全面印刷又はパターンよりやや大きな部分印刷を行い、予備乾燥後、コーティング面や印刷面にフォトマスクを密着させ、超高圧水銀灯を使用して露光を行ってパターンを焼き付ける。次いで現像及び洗浄を行い、必要に応じポストベークを行うことによりＣＦのパターンを形成することができる。
【００３４】
非感光性の被膜形成樹脂の例としては、セルロースアセテート系樹脂、ニトロセルロース系樹脂、スチレン系（共）重合体、ポリビニールブチラール系樹脂、アミノアルキッド系樹脂、ポリエステル系樹脂、アミノ樹脂変性ポリエステル系樹脂、ポリウレタン系樹脂、アクリルポリオールウレタン系樹脂、可溶性ポリアミド系樹脂、可溶性ポリイミド系樹脂、可溶性ポリアミドイミド系樹脂、可溶性ポリエステルイミド系樹脂、カゼイン、ヒドロキシエチルセルロース、スチレン−マレイン酸エステル系共重合体の水溶性塩、（メタ）アクリル酸エステル系（共）重合体の水溶性塩、水溶性アミノアルキッド系樹脂、水溶性アミノポリエステル系樹脂、水溶性ポリアミド系樹脂等が挙げられ、これらの樹脂は単独で或いは２種以上を組み合わせて使用する。
【００３５】
上記の非感光性顔料分散液を用いてＣＦのパターンを形成する場合には、非感光性顔料分散液、例えば、ＣＦ用印刷インキを用い、前記と同様なＣＦ基板上に直接着色パターンを、上記した各種の印刷方法にて印刷する方法、ＣＦ用水性電着塗装組成物を用いて電着塗装により基板上に着色パターンを形成させる方法、電子印刷方法や静電印刷方法、或いは転写性基材に上記の方式等で一旦着色パターンを形成させてからＣＦ用基板に転写する方法等が挙げられる。次いで常法に従い必要に応じてベーキングを行ったり、表面の平滑化のための研磨を行ったり、表面の保護のためのトップコーティングを行う。又、常法に従いブラックマトリックスを形成させて、ＲＧＢのＣＦを得ることができる。
【００３６】
【実施例】
次に合成例、実施例及び比較例を挙げて本発明を更に具体的に説明する。尚、文中部又は％とあるのは重量基準である。
合成例１
ｏ−ジクロロベンゼン６００部に６２部の１−アミノ−４−ベンゾイルアミノアントラキノンと２５部の塩化シアヌルを加え１３０℃で５時間撹拌する。冷却後、更にＮ，Ｎ，Ｎ″，Ｎ″−テトラエチルジエチレントリアミン５０部を添加して１７０℃にて３時間撹拌する。濾過後得られたフィルターケーキをエチルアルコールで洗浄し、乾燥後、前記具体例（１）の分散剤１を得た。
【００３７】
合成例２
合成例１と同様にして、塩化シアヌルに１−アミノ−４−ベンゾイルアミノアントラキノン及び３，３′−イミノビス（Ｎ，Ｎ−ジメチルプロピルアミン）を順次縮合反応させて前記具体例（２）の分散剤２を得た。
合成例３
合成例１と同様にして、塩化シアヌルに１−アミノ−４−ベンゾイルアミノアントラキノン、３−エチル−１０−メチル−３，６，１０−トリアザウンデカンを順次縮合反応させて前記具体例（３）の分散剤３を得た。
【００３８】
合成例４
合成例１と同様にして、塩化シアヌルに１−アミノ−４，５−ジベンゾイルアミノアントラキノン、３，３′−イミノビス（Ｎ，Ｎ−ジメチルプロピルアミン）を順次縮合反応させて前記具体例（４）の分散剤４を得た。
合成例５
合成例１と同様にして、塩化シアヌルに１−アミノ−４−ジベンゾイルアミノアントラキノン、アニリン、３，３′−イミノビス（Ｎ，Ｎ−ジメチルプロピルアミン）を順次縮合反応させて前記具体例（５）の分散剤５を得た。
【００３９】
合成例６
合成例１と同様にして、塩化シアヌルに１−アミノ−４−ベンゾイルアミノアントラキノン、５，１３−ジ（ｎ−ブチル）−５，９，１３−トリアザヘプタデカンを順次縮合反応させて前記具体例（６）の分散剤６を得た。
合成例７
合成例１と同様にして、塩化シアヌルに１−アミノ−４−ベンゾイルアミノアントラキノン、２，２′−ジピコリルアミンを順次縮合反応させて前記具体例（７）の分散剤７を得た。
【００４０】
合成例８
合成例１と同様にして、塩化シアヌルに１−アミノ−４−ベンゾイルアミノアントラキノン、３，３′−ジピコリルアミンを順次縮合反応させて前記具体例（８）の分散剤８を得た。
【００４１】
合成例９
合成例１と同様にして、塩化シアヌルに１−アミノ−４−ヒドロキシアントラキノン及び３，３’−イミノビス（Ｎ，Ｎ−ジメチルプロピルアミン）を順次に縮合反応させて前記具体例（９）の分散剤９を得た。
【００４２】
合成例１０
合成例１と同様にして、塩化シアヌルに１−アミノ−４−メトキシアントラキノン及び３，３’−イミノビス（Ｎ，Ｎ−ジメチルプロピルアミン）を順次に縮合反応させて前記具体例（１０）の分散剤１０を得た。
【００４３】
合成例１１
合成例１と同様にして、塩化シアヌルに１−アミノ−アクリドン−１，２（２’，４’−ジクロロ）アクリドン及び３，３’−イミノビス（Ｎ，Ｎ−ジメチルプロピルアミン）を順次に縮合反応させて前記具体例（１１）の分散剤１１を得た。
【００４４】
実施例１
アクリル樹脂（メタクリル酸／ブチルアクリレート／スチレン／ヒドロキシエチルアクリレート＝２５／５０／１５／１０のモル比で重合させたもの（分子量１２，０００））液（固形分３０％）にＰ．Ｒ．１７７と前記分散剤１及び溶剤（プロピレングリコールモノメチルエーテルアセテート（以下ＰＧＭＡｃと略す。））を下記の表１に示す如く配合し、プレミキシングの後、横型ビーズミルで分散し、赤色のベースカラーを得た。
【００４５】
実施例２〜４
前記分散剤１に代えて前記分散剤２（実施例２）、分散剤３（実施例３）及び分散剤４（実施例４）をそれぞれ使用したことを除いて実施例１と同様にして下記の表１に示した配合で３種の赤色のベースカラーを得た。
【００４６】
実施例５〜８
実施例１で使用したＰ．Ｒ．１７７に代えてＰ．Ｂ．１５：６を使用し、分散剤として前記分散剤５（実施例５）、前記分散剤６（実施例６）、前記分散剤７（実施例７）及び分散剤８（実施例８）をそれぞれ使用したことを除いて実施例１と同様の操作にて４種の青色のベースカラーを得た。配合を表１に示す。
【００４７】
実施例９
実施例１で使用したＰ．Ｒ．１７７に代えてＰ．Ｖ．２３を使用し、分散剤として前記分散剤２を使用したことを除いて実施例１と同様の操作にて紫色のベースカラーを得た。配合を表１に示す。この紫色のベースカラーはＣＦの製造に際して青色のベースカラーの補色に使用する。
【００４８】
実施例１０
実施例１で使用したＰ．Ｒ．１７７に代えてＰ．Ｙ．１３８を使用し、分散剤として前記分散剤２を使用したことを除いて実施例１と同様の操作にて黄色のベースカラーを得た。配合を表１に示す。この黄色のベースカラーはＣＦの製造に際して赤色及び緑色のベースカラーの補色に使用する。
【００４９】
参考例１
実施例１で使用したＰ．Ｒ．１７７に代えてＰ．Ｇ．３６を使用し、分散剤として下記構造式で表わされる分散剤を使用したことを除いて実施例１と同様の操作にて緑色のベースカラーを得た。配合を表１に示す。

【００５０】
比較例１
市販の赤色顔料の誘導体である分散剤（ＲＤと略記）を使用したことを除いて実施例１と同様にして、下記の表１に示した配合で赤色のベースカラーを得た。
比較例２
市販の青色顔料の誘導体である分散剤（ＢＤと略記）を使用したことを除いて実施例５と同様にして、下記の表１に示した配合で青色のベースカラーを得た。
【００５１】
比較例３
市販の紫色顔料の誘導体である分散剤（ＶＤと略記）を使用したことを除いて実施例９と同様にして、下記の表１に示した配合で紫色のベースカラーを得た。
比較例４
市販の黄色顔料の誘導体である分散剤（ＹＤと略記）を使用したことを除いて実施例１０と同様にして、下記の表１に示した配合で黄色のベースカラーを得た。
【００５２】

【００５３】
実施例１１
実施例１〜１０、参考例１及び比較例１〜４のベースカラーをスピンナーでガラス基板に塗布し、乾燥後、塗膜の最大透過率及び最大透過波長を測定した。又、ベースカラーを室温で一カ月間貯蔵し、その粘度の変化を測定した。その結果を表２に示す。赤色のベースカラー及び黄色のベースカラーについては６５０ｎｍの透過率の１／２になる波長を示した。
【００５４】

【００５５】
実施例１２
ＲＧＢのＣＦを得るために、下記の表３の配合によりＲ、Ｇ及びＢの感光性顔料分散液を得た。

【００５６】
シランカップリング剤処理を行ったガラス基板をスピンコーターにセットし、上記のＲの赤色のＣＦ用感光性樹脂液を最初３００ｒｐｍで５秒間、次いで１，２００ｒｐｍで５秒間の条件でスピンコートした。次いで８０℃で１０分間プリベークを行い、モザイク状のパターンを有するフォトマスクを密着させ、超高圧水銀灯を用い１００ｍＪ／ｃｍ²の光量で露光を行った。次いで専用現像液及び専用リンスで現像及び洗浄を行い、ガラス基板上に赤色のモザイク状パターンを形成させた。
【００５７】
引き続いて緑色モザイク状パターン及び青色のモザイク状パターンを上記のＧの緑色及びＢの青色のＣＦ用感光性樹脂液を用いて上記の方法に準じて塗布、焼き付けを行い、ＲＧＢのＣＦを得た。上記で得られたＣＦは優れた分光カーブ特性を有し、耐光性、耐熱性等の堅牢性に優れ、又、光の透過性にも優れた性質を有し、液晶カラーディスプレイ用ＣＦとして優れた性質を有した。
【００５８】
【発明の効果】
上記本発明によれば、特定の分散剤を使用することによって、顔料分散液を安定に製造することができ、又、最終的にＣＦ用顔料分散液として使用すると、得られた着色被膜は優れた分光カーブ特性を有し、鮮明で冴えた、透明感の高い、しかも耐光性、耐熱性、耐溶剤性、耐薬品性及び耐水性等の諸堅牢性に優れており、従ってこれらの優れた特性を有するＣＦを得ることができる。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a pigment dispersion (CF pigment dispersion) for producing color filters having excellent fluidity, storage stability, dispersion stability, and the like.
[0002]
[Prior art]
Conventionally, CF used for manufacturing liquid crystal color displays, image sensors, etc. is for CF in which three color pigments of red (R), green (G), and blue (B) are dispersed in a photosensitive resin liquid, respectively. The pigment dispersion is applied to the CF substrate by a spin coating method to form a colored film, and then the colored film is exposed and developed through a photomask to pattern the colored film, and a desired pixel is formed on the CF substrate. It is mainly produced by the method of forming.
[0003]
As the main pigment used in the production of CF, the green pigment is phthalocyanine green, for example C.I. I. Pigment Green (hereinafter referred to as PG) 36, the red pigment is an anthraquinone red, such as C.I. I. Pigment Red (hereinafter referred to as PR) 177, the blue pigment is phthalocyanine blue, for example, C.I. I. Pigment Blue (hereinafter referred to as P.B.) 15: 6 is generally used. However, there is a difference between the hue of these pigments and the color characteristics required for liquid crystal displays. A small amount of yellow pigment is used as a complementary color for green and red pigments, and a small amount of purple pigment is used as a complementary color for blue pigments. ing.
[0004]
[Problems to be solved by the invention]
The pigment dispersion for CF is usually composed of a pigment, a dispersant, a film-forming resin, and a liquid medium. As the film-forming resin, an acrylic resin having a high acid value that can be developed with an alkaline aqueous solution after the film is formed is mainly employed. However, pigment dispersions composed of the above-mentioned conventional pigments and high acid value acrylic resins often have poor storage stability, and pigment aggregation occurs during storage, and the viscosity of the pigment dispersion increases with time. It tends to be expensive.
[0005]
When producing CF using the pigment dispersion liquid with the above difficulties, the pigment dispersion liquid is applied to the CF substrate by spin coating. When the pigment dispersion to be used has a high viscosity or the pigment particles are aggregated and the pigment dispersion exhibits a thixotropic viscosity, the applied pigment dispersion rises at the center of the substrate. Such a situation may cause unevenness or density difference in the hue of the colored coating between the central portion and the peripheral portion of the substrate when producing a large-screen CF.
[0006]
Therefore, although the pigment dispersion for CF is usually in the range of 5 to 10% by weight, the dispersion state of the pigment is stable, the pigment particles do not aggregate, and 5 to 20 centipoise. It must be low in viscosity and excellent in storage stability. In order to satisfy the required performance for such a CF pigment dispersion, various dispersants have been proposed in JP-A-60-237403 and JP-A-60-247603. These pigment dispersants ( (Hereinafter simply referred to as a dispersant) does not exhibit sufficiently low viscosity and dispersion stability, and the maximum transmittance wavelength of CF RGB pixels prepared from these pigment dispersions is longer. Or, it shifts to the short wavelength side, and has a defect that the color quality is lowered as CF for liquid crystal display.
[0007]
As a result of diligent research on the development of a dispersant capable of improving the color quality and lowering the viscosity of a CF pigment dispersion, the present inventors have solved the above-mentioned disadvantages of the conventional dispersants. As a result, triazinylaminoanthraquinone series Specific derivatives of the dye include phthalocyanine blue which is a blue main pigment and a purple pigment which is a complementary color pigment thereof, and an anthraquinone red (PR 177) and a pyrrolopyrrole pigment (PR) which are red main pigments. .254, P.O.71) and its complementary pigment, yellow pigment, which is commonly used as an excellent dispersant, can achieve low viscosity of the pigment dispersion, and can be used for storage of the pigment dispersion. As a result, it was found that the most important transparency as CF is prevented, and the present invention has been completed.
[0008]
[Means for Solving the Problems]
That is, the present invention comprises a pigment dispersion for CF, comprising a pigment, a dispersant, a film-forming resin, and a liquid medium, and the dispersant is composed of a compound represented by the following general formula (I): A manufacturing method and a CF are provided.

(However, X in the above formula is a hydroxyl group, an alkoxy group, a primary to tertiary amino group or an acylamino group, and Y is a hydrogen atom, a hydroxyl group, an alkoxy group, a primary to tertiary amino group or an acylamino group at the 4-position. An anthraquinonylamino group, a phenylamino group or a phenoxy group, A and B are an alkyl group, a cycloalkyl group or an aryl group, and at least one of A or B has at least one substituent having a basic nitrogen atom. Z represents a hydrogen atom, a cyano group, a halogen atom, an alkyl group, an alkoxy group, a nitro group, a benzoylamino group or a benzoyl group (position 3), and the benzoyl group is bonded to X to form an acridone ring. You may do it.)
The “substituent having a basic nitrogen atom” is a primary, secondary or tertiary amino group, a quaternary ammonium group and / or a pyridinium group, and a tertiary amino group is particularly preferable.
[0009]
The CF pigment dispersion of the present invention is characterized in that a specific derivative of a triazinylaminoanthraquinone dye is used as a pigment dispersant. By using the dispersant, the pigment particles of the CF pigment dispersion are used. Aggregation is prevented. As a result, the CF pigment dispersion has a reduced structural viscosity, has a low viscosity, suppresses thickening gelation of the pigment dispersion, and increases storage stability. Further, the dispersant represented by the general formula (I) itself has a color tone of yellowish red to blueish red, and this dispersant is used as a blue pigment and a purple pigment which is a complementary color pigment, and red. When the pigment dispersion is used as a dispersant for a pigment and a yellow pigment that is a complementary color pigment, and the obtained pigment dispersion is used for forming a CF pixel for a liquid crystal display or the like, a pixel having a desired color quality can be formed.
[0010]
DETAILED DESCRIPTION OF THE INVENTION
Next, the present invention will be described in detail with reference to preferred embodiments.
Examples of the dispersing agent represented by the general formula (I) used in the present invention include the production methods disclosed in Japanese Patent Publication No. 46-33232, Japanese Patent Publication No. 46-33233, and Japanese Patent Publication No. 46-34518. Or it is manufactured by the method according to it. For example, 1 mol of 1-amino-4-benzoylaminoanthraquinone and 1 mol of aniline or phenol and 1 mol of cyanuric chloride are added at 130 to 160 ° C. in an inert solvent such as o-dichlorobenzene. 6 hours, and 1 mol of polyamine having at least one secondary amino group and at least one tertiary amino group and no primary amino group was added at 150 to 170 ° C. for 3 to 4 hours. It is obtained by reacting under reaction conditions.
[0011]
Examples of the “polyamine having at least one secondary amino group and at least one tertiary amino group and having no primary amino group” used in the above method include:
N, N, N'-trimethyl-ethylenediamine N, N-dimethyl-N'-ethyl-ethylenediamine N, N-diethyl-N'-methyl-ethylenediamine N, N-dimethyl-N'-ethyl-propylenediamine N, N , N'-trimethyl-propylenediamine N, N, N'-triethyl-propylenediamine N, N, N'-trimethyl-hexamethylenediamine N, N-diethyl-N'-methyl-p-phenylenediamine N, N- Dipropyl-N'-methyl-p-phenylenediamine N, N, N'-trimethyl-p-phenylenediamine N, N, N'-trimethyl-m-phenylenediamine N, N, N'-triethyl-p-phenylenediamine N, N-diethyl-N'-methyl-1,4-diaminocyclohexane N, N-diethyl-N'-me 1,3-diaminocyclohexane N, N, N'-trimethyl-1,4-diaminocyclohexane N, N, N'-triethyl-1,4-diaminocyclohexane N-methylpiperazine N-ethylpiperazine N-isobutylpiperazine 2-chlorophenyl piperazine N- (2-pyridyl) piperazine N- (4-pyridyl) piperazine methyl homopiperazine and the like can be mentioned.
[0012]
In addition to the above compounds, particularly preferred are:
N, N, N ″, N ″ -tetramethyldiethylenetriamine N, N, N ″, N ″ -tetra (n-propyl) diethylenetriamine N, N, N ″, N ″ -tetra (i-propyl) diethylenetriamine N, N , N ″, N ″ -tetra (n-butyl) diethylenetriamine N, N, N ″, N ″ -tetra (i-butyl) diethylenetriamine N, N, N ″, N ″ -tetra (s-butyl) diethylenetriamine N, N, N ″, N ″ -tetra (t-butyl) diethylenetriamine 3,3′-iminobis (N, N-dimethylpropylamine)
3,3'-iminobis (N, N-diethylpropylamine)
3,3′-iminobis [N, N-di (n-propyl) propylamine]
3,3′-iminobis [N, N-di (i-propyl) propylamine]
3,3′-iminobis [N, N-di (n-butyl) propylamine]
3,3′-iminobis [N, N-di (i-butyl) propylamine]
3,3′-iminobis [N, N-di (s-butyl) propylamine]
3,3′-iminobis [N, N-di (t-butyl) propylamine]
4,4'-iminobis (N, N-dimethylbutylamine)
4,4'-iminobis (N, N-diethylbutylamine)
2,9-dimethyl-2,5,9-triazadecane 2,12-dimethyl-2,6,12-triazatridecane 2,12-dimethyl-2,5,12-triazatridecane 2,16-dimethyl 2,9,16-triazaheptadecane 3-ethyl-10-methyl-3,6,10-triazaundecane 5,13-di (n-butyl) -5,9,13-triazaheptadecane 2 2,2'-dipicolylamine 3,3'-dipicolylamine and the like.
[0013]
Among the dispersants obtained by the above method and the like, a preferable dispersant in the present invention is a compound represented by the following general formula (1), and a more preferable dispersant is represented by the following general formula (2). Particularly preferred dispersants are compounds represented by the following general formula (3).

(However, X, Y and Z in the above formula are as defined above, and R _{1 to} R ₄ may be the same or different, and may be a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group. R ₁ and R ₂ and / or R ₃ and R ₄ may be bonded to adjacent nitrogen atoms to form a heterocyclic ring which may further contain a nitrogen atom, an oxygen atom or a sulfur atom, and R ₅ and R ₆ are an alkylene group, a cycloalkylene group or an arylene group.
[0014]

(However, X, Y, Z and R _{1 to} R ₄ in the above formula are as defined above, and n and m are integers of 2 to 30.)
[0015]
The acylamino group in the above formula (I) and the above formulas (1) to (2) is a group represented by —NHCOR. For example, R is a phenyl group, a methyl group, an ethyl group, a propyl group, A butyl group and the like.

(However, X in the above formula is a benzoylamino group, Z is a hydrogen atom, R _{1 to} R ₄ may be the same or different, and a methyl group or an ethyl group, and n and m are 2 or 3) Represents.)
[0016]
Specific examples of preferred dispersants in the present invention are listed below, but the dispersant used in the present invention is not limited to these examples. In the following formula, X represents a benzoylamino group.

[0017]

[0018]

[0019]

[0020]

[0021]

[0022]

[0023]

[0024]

[0025]

[0026]

And the quaternary ammonium compound of the said specific examples 1-6 and 9-11 and the pyridinium compound of specific examples 7-8.
[0027]
The pigment dispersion for CF of the present invention comprises the above dispersant, pigment, film-forming resin, and liquid medium. When preparing the pigment dispersion for CF of the present invention, the dispersant is used in a proportion of 0.5 to 50 parts by weight, preferably 1 to 30 parts by weight, based on 100 parts by weight of the pigment. If the amount used is less than 0.5 parts by weight, the effect of the dispersant used in the present invention is hardly recognized. On the other hand, even if the amount used exceeds 50 parts by weight, the effect corresponding to the amount used is not obtained.
[0028]
Suitable pigments used in the CF pigment dispersion in the present invention include, for example, C.I. I. Pigment Red (hereinafter referred to as PR) 177, P.R. R. 254, P.I. R. 242, P.I. R. 209, p. R. 224; C.I. I. Pigment Green (hereinafter referred to as PG) 36, P.G. G. 7; I. Pigment Blue (hereinafter referred to as P.B.) 15: 6, P.I. B. 60: C.I. I. Pigment Yellow (hereinafter referred to as P.Y.) 138, P.I. Y. 185, P.I. Y. 150, P.I. Y. 139, P.I. Y. 83: C.I. I. Pigment violet (hereinafter referred to as PV) 23, C.I. I. Pigment black (hereinafter referred to as P.BL.) 6, P.P. BL. 7 etc. are used. In addition, these pigments may be used in an appropriate mixture in order to compensate for the difference in hue and color characteristics required for the liquid crystal display.
[0029]
As a method for producing the CF pigment dispersion of the present invention, a pigment and a dispersant are added to an organic solvent solution or an aqueous solution containing an appropriate film-forming resin, and premixing is performed, and then the pigment is subjected to a dispersion treatment. For example, the pigment and the dispersant to be used are uniformly mixed and pulverized by a dispersing machine such as a horizontal medium dispersing machine, a vertical medium dispersing machine, a pin mill, an attritor, or a ball mill, and this is added and mixed in a liquid containing a film forming resin. A method in which a pigment is uniformly suspended in water or an organic solvent, a solution containing a dispersant is added to and mixed with the pigment, and a dispersant is deposited on the pigment particle surface in a solution containing a film-forming resin. A method of adding and mixing, a method of dissolving a pigment and a dispersant in sulfuric acid and the like, then precipitating the sulfuric acid solution in water, separating both as a solid solution, and adding and mixing this into a liquid containing a film-forming resin, etc. It is done.
[0030]
In the present invention, as the liquid containing a film-forming resin for dispersing a pigment to form a pigment dispersion, a liquid containing a film-forming resin used in a conventionally known CF pigment dispersion is used. Further, an organic solvent, water, or a mixture of an organic solvent and water is used as the liquid medium. Examples of the organic solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, and ethylene glycol monoethyl ether. Examples include acetate, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, 3-methoxybutyl acetate, cyclohexanone, and ethyl lactate. Moreover, conventionally well-known additives, for example, additives, such as a dispersing aid, a smoothing agent, and an adhesive agent, can be added to a pigment dispersion as needed. The ratio of the pigment to the film-forming resin in the liquid containing the film-forming resin is preferably in the range of 5 to 500 parts by weight with respect to 100 parts by weight of the film-forming resin.
[0031]
The liquid containing the film-forming resin is appropriately selected depending on the coating method, the pixel pattern forming method, and the like, and a liquid containing a photosensitive film-forming resin and a liquid containing a non-photosensitive film-forming resin are used. Examples of the liquid containing the photosensitive film-forming resin include a liquid containing a photosensitive film-forming resin used for ultraviolet curable ink, electron beam curable ink, and the like. For example, varnish used for printing ink such as letterpress ink, lithographic ink, intaglio gravure ink, stencil screen ink, varnish used for electrodeposition coating, varnish used for developer of electronic printing and electrostatic printing, thermal transfer ribbon Varnish to be used.
[0032]
Examples of photosensitive film-forming resins include photosensitive cyclized rubber resins, photosensitive phenol resins, photosensitive polyacrylate resins, photosensitive polyamide resins, photosensitive polyimide resins, unsaturated polyester resins, polyesters. Examples thereof include photosensitive resins such as acrylate resins, polyepoxy acrylate resins, polyurethane acrylate resins, polyether acrylate resins, and polyol acrylate resins. These resins are used alone or in combination of two or more. A preferred resin among the photosensitive film-forming resins is an acrylate-based alkali developable resin having a free carboxyl group in the molecule. Various monomers can be further added as reactive diluents to the liquid containing these photosensitive film-forming resins.
[0033]
In addition, a photopolymerization initiator such as benzoin ether or benzophenone is added to a pigment dispersion containing a photosensitive film forming resin, and kneaded by a conventionally known method to obtain a photocurable photosensitive pigment dispersion. it can. Moreover, it can replace with said photoinitiator and can use it as a thermosetting pigment dispersion liquid using a thermal polymerization initiator.
When a CF pattern is formed using the above photosensitive pigment dispersion, the photosensitive pigment dispersion is used on a transparent CF substrate such as glass using a spin coater, a low-speed rotary coater, a roll coater, a knife coater, or the like. Apply full-surface coating, or perform full-surface printing by various printing methods or partial printing slightly larger than the pattern, and after preliminary drying, attach a photomask to the coated surface or printed surface and expose using an ultra-high pressure mercury lamp. Go and burn the pattern. Next, development and washing are performed, and post-baking is performed as necessary to form a CF pattern.
[0034]
Examples of non-photosensitive film-forming resins include cellulose acetate resins, nitrocellulose resins, styrene (co) polymers, polyvinyl butyral resins, amino alkyd resins, polyester resins, amino resin modified polyester resins Resin, polyurethane resin, acrylic polyol urethane resin, soluble polyamide resin, soluble polyimide resin, soluble polyamideimide resin, soluble polyesterimide resin, casein, hydroxyethyl cellulose, styrene-maleic ester copolymer water-soluble Salts, water-soluble salts of (meth) acrylic acid ester (co) polymers, water-soluble amino alkyd resins, water-soluble amino polyester resins, water-soluble polyamide resins, and the like. Or a combination of two or more To use Te.
[0035]
When forming a CF pattern using the above-mentioned non-photosensitive pigment dispersion, a non-photosensitive pigment dispersion, for example, a CF printing ink is used, and a colored pattern is directly formed on a CF substrate similar to the above. A method of printing by the above-described various printing methods, a method of forming a colored pattern on a substrate by electrodeposition coating using an aqueous electrodeposition coating composition for CF, an electronic printing method, an electrostatic printing method, or a transferable group Examples thereof include a method in which a colored pattern is once formed on a material by the above method and then transferred to a CF substrate. Subsequently, baking is performed as necessary according to a conventional method, polishing for smoothing the surface, or top coating for protecting the surface is performed. Further, an RGB CF can be obtained by forming a black matrix according to a conventional method.
[0036]
【Example】
Next, the present invention will be described more specifically with reference to synthesis examples, examples and comparative examples. In the text, “%” or “%” is based on weight.
Synthesis example 1
62 parts of 1-amino-4-benzoylaminoanthraquinone and 25 parts of cyanuric chloride are added to 600 parts of o-dichlorobenzene and stirred at 130 ° C. for 5 hours. After cooling, 50 parts of N, N, N ″, N ″ -tetraethyldiethylenetriamine is further added and stirred at 170 ° C. for 3 hours. The filter cake obtained after filtration was washed with ethyl alcohol and dried to obtain Dispersant 1 of Specific Example (1).
[0037]
Synthesis example 2
In the same manner as in Synthesis Example 1, 1-amino-4-benzoylaminoanthraquinone and 3,3′-iminobis (N, N-dimethylpropylamine) were sequentially condensed with cyanuric chloride to disperse the specific example (2). Agent 2 was obtained.
Synthesis example 3
In the same manner as in Synthesis Example 1, cyanuric chloride was subjected to a condensation reaction of 1-amino-4-benzoylaminoanthraquinone and 3-ethyl-10-methyl-3,6,10-triazaundecane in this order to give the specific example (3). Dispersant 3 was obtained.
[0038]
Synthesis example 4
In the same manner as in Synthesis Example 1, 1-amino-4,5-dibenzoylaminoanthraquinone and 3,3′-iminobis (N, N-dimethylpropylamine) were sequentially condensed with cyanuric chloride, and the above-mentioned specific example (4 Dispersant 4) was obtained.
Synthesis example 5
In the same manner as in Synthesis Example 1, cyanuric chloride was subjected to a condensation reaction of 1-amino-4-dibenzoylaminoanthraquinone, aniline, and 3,3′-iminobis (N, N-dimethylpropylamine) in this order, and the specific example (5 Dispersant 5) was obtained.
[0039]
Synthesis Example 6
In the same manner as in Synthesis Example 1, cyanuric chloride was subjected to sequential condensation reaction of 1-amino-4-benzoylaminoanthraquinone and 5,13-di (n-butyl) -5,9,13-triazaheptadecane to the above-mentioned specific examples. Dispersant 6 of Example (6) was obtained.
Synthesis example 7
In the same manner as in Synthesis Example 1, 1-amino-4-benzoylaminoanthraquinone and 2,2′-dipicolylamine were sequentially condensed with cyanuric chloride to obtain Dispersant 7 of Specific Example (7).
[0040]
Synthesis Example 8
In the same manner as in Synthesis Example 1, 1-amino-4-benzoylaminoanthraquinone and 3,3′-dipicolylamine were sequentially condensed with cyanuric chloride to obtain Dispersant 8 of Specific Example (8).
[0041]
Synthesis Example 9
In the same manner as in Synthesis Example 1, 1-amino-4-hydroxyanthraquinone and 3,3′-iminobis (N, N-dimethylpropylamine) were sequentially condensed to cyanuric chloride to disperse the specific example (9). Agent 9 was obtained.
[0042]
Synthesis Example 10
In the same manner as in Synthesis Example 1, 1-amino-4-methoxyanthraquinone and 3,3′-iminobis (N, N-dimethylpropylamine) were sequentially condensed with cyanuric chloride to disperse the specific example (10). Agent 10 was obtained.
[0043]
Synthesis Example 11
In the same manner as in Synthesis Example 1, 1-amino-acridone-1,2 (2 ′, 4′-dichloro) acridone and 3,3′-iminobis (N, N-dimethylpropylamine) are sequentially condensed to cyanuric chloride. By reacting, the dispersant 11 of the specific example (11) was obtained.
[0044]
Example 1
An acrylic resin (polymerized with a molar ratio of methacrylic acid / butyl acrylate / styrene / hydroxyethyl acrylate = 25/50/15/10 (molecular weight 12,000)) was added to a liquid (solid content 30%). R. 177, dispersant 1 and solvent (propylene glycol monomethyl ether acetate (hereinafter abbreviated as PGMAc)) are blended as shown in Table 1 below, and after premixing, they are dispersed by a horizontal bead mill to obtain a red base color. It was.
[0045]
Examples 2-4
In the same manner as in Example 1, except that Dispersant 2 (Example 2), Dispersant 3 (Example 3) and Dispersant 4 (Example 4) were used instead of Dispersant 1, respectively. Three red base colors were obtained with the formulation shown in Table 1.
[0046]
Examples 5-8
The P.P. used in Example 1 was used. R. P. B. 15: 6 is used, and the dispersant 5 (Example 5), the dispersant 6 (Example 6), the dispersant 7 (Example 7), and the dispersant 8 (Example 8) are used as dispersants, respectively. Four blue base colors were obtained by the same operation as in Example 1 except that it was used. The formulation is shown in Table 1.
[0047]
Example 9
The P.P. used in Example 1 was used. R. P. V. 23 was used, and a purple base color was obtained in the same manner as in Example 1 except that the dispersant 2 was used as a dispersant. The formulation is shown in Table 1. This purple base color is used as a complementary color to the blue base color in the production of CF.
[0048]
Example 10
The P.P. used in Example 1 was used. R. P. Y. 138 was used, and a yellow base color was obtained in the same manner as in Example 1 except that the dispersant 2 was used as a dispersant. The formulation is shown in Table 1. This yellow base color is used as a complementary color of the red and green base colors in the production of CF.
[0049]
Reference example 1
The P.P. used in Example 1 was used. R. P. G. 36 was used, and a green base color was obtained in the same manner as in Example 1 except that the dispersant represented by the following structural formula was used as the dispersant. The formulation is shown in Table 1.

[0050]
Comparative Example 1
A red base color was obtained in the same manner as in Example 1 except that a dispersant (abbreviated as RD), which is a commercially available red pigment derivative, was used.
Comparative Example 2
A blue base color was obtained in the same manner as in Example 5 except that a dispersing agent (abbreviated as BD), which is a commercially available blue pigment derivative, was used.
[0051]
Comparative Example 3
A purple base color was obtained with the formulation shown in Table 1 below in the same manner as in Example 9, except that a dispersant (abbreviated as VD) which is a derivative of a commercially available purple pigment was used.
Comparative Example 4
A yellow base color was obtained with the formulation shown in Table 1 below in the same manner as in Example 10 except that a dispersant (abbreviated as YD) which is a derivative of a commercially available yellow pigment was used.
[0052]

[0053]
Example 11
The base colors of Examples 1 to 10, Reference Example 1 and Comparative Examples 1 to 4 were applied to a glass substrate with a spinner, and after drying, the maximum transmittance and the maximum transmission wavelength of the coating film were measured. The base color was stored at room temperature for one month and the change in viscosity was measured. The results are shown in Table 2. For the red base color and the yellow base color, a wavelength that is ½ of the transmittance at 650 nm is shown.
[0054]

[0055]
Example 12
In order to obtain RGB CF, photosensitive pigment dispersions of R, G and B were obtained according to the formulation shown in Table 3 below.

[0056]
The glass substrate that had been treated with the silane coupling agent was set on a spin coater, and the above-mentioned red red photosensitive resin solution for CF was spin-coated at 300 rpm for 5 seconds and then at 1200 rpm for 5 seconds. Next, prebaking was performed at 80 ° C. for 10 minutes, a photomask having a mosaic pattern was brought into close contact, and exposure was performed with an ultrahigh pressure mercury lamp at a light amount of 100 mJ / cm ² . Next, development and washing were performed with a dedicated developer and a dedicated rinse, and a red mosaic pattern was formed on the glass substrate.
[0057]
Subsequently, the green mosaic pattern and the blue mosaic pattern were applied and baked in accordance with the above method using the above G green and B blue CF photosensitive resin liquids to obtain RGB CF. . The CF obtained above has excellent spectral curve characteristics, excellent fastness such as light resistance and heat resistance, and excellent light transmission properties, and is excellent as a CF for liquid crystal color displays. Had the properties.
[0058]
【The invention's effect】
According to the present invention, a pigment dispersion can be stably produced by using a specific dispersant, and when used as a CF pigment dispersion, the resulting colored coating is excellent. It has excellent spectral curve characteristics, clearness, high transparency, and excellent fastness such as light resistance, heat resistance, solvent resistance, chemical resistance and water resistance. CF having characteristics can be obtained.

Claims (13)

A pigment dispersion for a color filter comprising a pigment, a dispersant, a film-forming resin, and a liquid medium, wherein the dispersant is composed of a compound represented by the following general formula (I).

(However, X in the above formula is a hydroxyl group, an alkoxy group, a primary to tertiary amino group or an acylamino group, and Y is a hydrogen atom, a hydroxyl group, an alkoxy group, a primary to tertiary amino group or an acylamino group at the 4-position. An anthraquinonylamino group, a phenylamino group or a phenoxy group, A and B are an alkyl group, a cycloalkyl group or an aryl group, and at least one of A or B has at least one substituent having a basic nitrogen atom. Z represents a hydrogen atom, a cyano group, a halogen atom, an alkyl group, an alkoxy group, a nitro group, a benzoylamino group or a benzoyl group (position 3), and the benzoyl group is bonded to X to form an acridone ring. You may do it.) The at least one substituent having a basic nitrogen atom is a primary, secondary or tertiary amino group, a quaternary ammonium group or a pyridinium group, and two or more substituents having the basic nitrogen atom 2. The pigment dispersion for color filter according to claim 1, wherein when present, they may be the same or different. The pigment dispersion for a color filter according to claim 1, wherein the compound represented by the general formula (I) is represented by the following general formula (1).

(However, X, Y and Z in the above formula are as defined above, and R _{1 to} R ₄ may be the same or different, and may be a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group. R ₁ and R ₂ and / or R ₃ and R ₄ may be bonded to adjacent nitrogen atoms to form a heterocyclic ring which may further contain a nitrogen atom, an oxygen atom or a sulfur atom, and R ₅ and R ₆ are an alkylene group, a cycloalkylene group or an arylene group.) The pigment dispersion for a color filter according to claim 1, wherein the compound represented by the general formula (I) is represented by the following general formula (2).

(However, X, Y and Z in the above formula are as defined above, and R _{1 to} R ₄ may be the same or different, and may be a substituted or unsubstituted alkyl group or a substituted or unsubstituted cycloalkyl group. R ₁ and R ₂ and / or R ₃ and R ₄ may be bonded to the adjacent nitrogen atom to form a heterocyclic ring which may further contain a nitrogen atom, an oxygen atom or a sulfur atom, and n And m is an integer of 2 to 30.) The pigment dispersion for a color filter according to claim 1, wherein the compound represented by the general formula (I) is represented by the following general formula (3).

(However, X in the above formula is a benzoylamino group, Z is a hydrogen atom, R _{1 to} R ₄ may be the same or different, and a methyl group or an ethyl group, and n and m are 2 or 3) Represents.) The pigment dispersion for a color filter according to claim 1, wherein the pigment is a red pigment, a blue pigment, a yellow pigment, a violet pigment, or a black pigment. The pigment dispersion for a color filter according to claim 1, comprising a dispersant at a ratio of 0.5 to 50 parts by weight with respect to 100 parts by weight of the pigment. The pigment dispersion for a color filter according to claim 1, comprising 5 to 500 parts by weight of pigment with respect to 100 parts by weight of the film-forming resin. The pigment dispersion for a color filter according to claim 1, wherein the film-forming resin contains a photosensitive resin. The pigment dispersion for a color filter according to claim 1, wherein the photosensitive resin is an acrylate-based alkali developable resin having a free carboxyl group in the molecule. The pigment is a red pigment, blue pigment, yellow pigment, purple pigment or black pigment, the dispersant is a compound represented by the following general formula (3), and the film-forming resin has a free carboxyl group in the molecule. The pigment dispersion for a color filter according to claim 1, which is an acrylate-based alkali developable resin.

(However, X in the above formula is a benzoylamino group, Z is a hydrogen atom, R _{1 to} R ₄ may be the same or different, and a methyl group or an ethyl group, and n and m are 2 or 3) Represents.) In the manufacturing method of the color filter including the process of forming a coloring pattern in the board | substrate for color filters, a coloring pattern is formed using the pigment dispersion liquid of any one of Claims 1-11, It is characterized by the above-mentioned. A method for producing a color filter. A color filter manufactured by the method according to claim 12.