JP4070683B2 - 着色感光性組成物、カラーフィルター及びこれを用いて形成された液晶表示装置 - Google Patents
着色感光性組成物、カラーフィルター及びこれを用いて形成された液晶表示装置 Download PDFInfo
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- JP4070683B2 JP4070683B2 JP2003286365A JP2003286365A JP4070683B2 JP 4070683 B2 JP4070683 B2 JP 4070683B2 JP 2003286365 A JP2003286365 A JP 2003286365A JP 2003286365 A JP2003286365 A JP 2003286365A JP 4070683 B2 JP4070683 B2 JP 4070683B2
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Description
又、本発明の他の要旨は、前記アルカリ可溶性樹脂(3)が、前記一般式(I)及び(II)で表される繰り返し単位を有し、酸価が10〜300mgKOH/gの重合体であることを特徴とする着色感光性組成物に存する。
(2)光重合開始剤
(3)アルカリ可溶性樹脂
(4)重合性モノマー又はオリゴマー
(5)色材
(6)溶剤
(7)任意成分。
本発明の不飽和二重結合を有する光重合性高分子化合物は、下記一般式(I)及び(II)で示される繰り返し単位を有する重合体である。
X1及びX2は、各々独立に、水素原子又はメチル基を表す。R1は分岐状アルキル基であり、具体的には、i−プロピル基、i−ブチル基、t−ブチル基、2−ブチル基、2−ペンチル基、2,2−ジメチルプロピル基、2−メチルブチル基、3−メチルブチル基、1−メチルペンチル基、1−エチルブチル基、2−メチルペンチル基、2−エチルブチル基、3−メチルペンチル基等をあげることができる。
一般式(I)及び(II)、場合によっては更に一般式(III)で表される繰り返し単位を有する重合体を製造するには、それぞれの繰り返し単位に相当するモノマーを所定の割合で重合すればよい。また、(メタ)アクリル酸、(メタ)アクリル酸エステル、(メタ)アクリル酸アミド、(メタ)アクリロニトリルなどを重合又は共重合した後、特定の側鎖を、所望の程度変性する方法によっても製造できる。
本発明の着色感光性組成物に使用する重合開始剤としては、単量体等が重合反応を起こすものであれば特に制限はない。即ち、光を直接吸収するか光増感されて、分解反応または水素引き抜き反応を起こし、重合活性ラジカルを発生する機能を有する化合物が使用できる。
2−(4−メトキシフェニル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(4−メトキシナフチル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(4−エトキシナフチル)−4,6−ビス(トリクロロメチル)−s−トリアジン、2−(4−エトキシカルボニルナフチル)−4,6−ビス(トリクロロメチル)−s−トリアジン等のハロメチル化トリアジン誘導体;
2−トリクロロメチル−5−(2′−ベンゾフリル)−1,3,4−オキサジアゾール、2−トリクロロメチル−5−〔β−(2′−ベンゾフリル)ビニル〕−1,3,4−オキサジアゾール、2−トリクロロメチル−5−〔β−(2′−(6’’−ベンゾフリル)ビニル)〕−1,3,4−オキサジアゾール、2−トリクロロメチル−5一フリル−1,3,4−オキサジアゾール等のハロメチル化オキサジアゾール誘導体;
2−(2′−クロロフェニル)−4,5−ジフェニルイミダソール2量体、2−(2′−クロロフェニル)−4,5−ビス(3′−メトキシフェニル)イミダゾール2量体、2−(2′−フルオロフェニル)−4,5−ジフェニルイミダゾール2量体、2−(2′−メトキシフエニル)−4,5−ジフェニルイミダゾール2量体、(4′−メトキシフエニル)−4,5−ジフェニルイミダゾール2量体等のイミダゾール誘導体;ベンゾインメチルエーテル、ベンゾインフェニルエーテル、ベンゾインイソブチルエーテル、ベンゾインイソプロピルエーテル等のベンゾインアルキルエーテル類;
2−メチルアントラキノン、2−エチルアントラキノン、2−t−ブチルアントラキノン、1−クロロアントラキノン等のアントラキノン誘導体;
ベンゾフェノン、ミヒラーケトン、2−メチルベンゾフェノン、3−メチルベンゾフェノン、4−メチルベンゾフェノン、2−クロロベンゾフェノン、4−ブロモベンゾフェノン、2−カルボキシベンゾフェノン等のベンゾフェノン誘導体;
2,2−ジメトキシ−2−フェニルアセトフェノン、2,2−ジエトキシアセトフェノン、1−ヒドロキシシクロへキシルフェニルケトン、α−ヒドロキシ−2−メチルフェニルプロパノン、1−ヒドロキシ−1−メチルエチル−(p−イソプロピルフェニル)ケトン、1−ヒドロキシ−1−(p−ドデシルフェニル)ケトン、2−メチル−(4′−(メチルチオ)フェニル)−2−モルホリノ−1−プロパノン、1,1,1−トリクロロメチル−(p一ブチルフェニル)ケトン等のアセトフェノン誘導体;
チオキサントン、2−エチルチオキサントン、2−イソプロピルチオキサントン、2−クロロチオキサントン、2,4−ジメチルチオキサントン、2、4−ジエチルチオキサントン、2,4−ジイソプロピルチオキサントン等のチオキサントン誘導体;
p−ジメチルアミノ安息香酸エチル、P−ジエチルアミノ安息香酸エチル等の安息香酸エステル誘導体;
9-フェニルアクリジン、9-(p-メトキシフェニル)アクリジン等のアクリジン誘導体;
9,10-ジメチルベンズフェナジン等のフェナジン誘導体;
ベンズアンスロン等のアンスロン誘導体;
ジ−シクロペンタジエニル−Ti−ジ−クロライド、ジ−シクロペンタジェニル−Ti−ビス−フェニル、ジ−シクロペンタジェニル−Ti−ビス−2,3,4,5,6−ペンタフルオロフェニル−1一イル、ジ−シクロペンタジェニル−Ti−ビス−2,3,5,6−テトラフルオロフェニル−1−イル、ジ−シクロペンタジェニル−Ti−ビス−2,4,6−トリフルオロフェニ−1−イル、ジ−シクロペンタジェニル−Ti−2,6一ジープルオロフェニ−1−イル、ジ−シクロペンタジェニル−Ti−2,4−ジ−フルオロフエニ−1−イル、ジ−メチルシクロペンタジェニル−Ti−ビス−2,3,4,5,6−ペンタフルオロフェニ−1−イル、ジ−メチルシクロペンタジェニル−Ti−ビス−2,6−ジ−フルオロフェニ−1−イル、ジ−シクロペンタジェニル−Ti−2,6−ジ−フルオロ−3−(ピル−1−イル)−フェニ−1−イル等のチタノセン誘導体。
本発明の着色感光性組成物に使用するアルカリ可溶性樹脂は、側鎖又は主鎖にカルボキシル基又はフェノール性水酸基を含有するものである。これらの官能基を有する樹脂を使用すれば、アルカリ溶液での現像が可能となる。好ましくは、高アルカリ現像性を示す樹脂である、カルボキシル基を有する樹脂、例えば、(メタ)アクリル酸(共)重合体、スチレン/無水マレイン酸樹脂、ノボラックエポキシアクリレートの酸無水物変性樹脂等が好ましい。特に好ましいのは、(メタ)アクリル酸又はカルボキシル基を有する(メタ)アクリル酸エステルを含む(共)重合体である。この樹脂は、現像性、透明性に優れ、かつ、様々な単量体を選択して種々の共重合体を得ることが可能なため、性能及び製造方法を制御しやすい点において極めて有利である。
本発明の着色感光性組成物に使用する重合性モノマー又はオリゴマーとしては、重合可能な低分子化合物であれば特に制限はない。例えば、エチレン性二重結合を少なくとも1つ有する付加重合可能な化合物(以下、「エチレン性化合物」と称す)が好ましい。エチレン性化合物とは、本発明の着色感光性組成物が活性光線の照射を受けた場合、光重合開始剤の作用により付加重合し、硬化するようなエチレン性二重結合を有する化合物である。なお、本発明における「モノマー又はオリゴマー」とは、いわゆる高分子物質に相対する概念を意味し、狭義の単量体以外に二量体、三量体、オリゴマーをも含有する概念を意味する。重量平均分子量としては、5000未満、好ましくは3000未満、更に好ましくは50〜2000の範囲から選択される。
本発明の着色感光性組成物に使用する色材としては、各種染顔料が使用できるが、耐熱性、耐光性等の点から顔料が好ましい。
本発明の着色感光性組成物においては、溶剤を使用する。このような溶剤としては、通常、感光性材料としてのバインダー樹脂、単量体又はオリゴマー、光重合開始剤、加速剤、増感色素、界面活性剤等の組成物中の成分を溶解しうるものであれば特に制限はないが、特に、この他に色材としての染料、顔料分散体を溶解、または安定的に保持できる性質が一般的に必要とされる。
エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールジプロピルエーテル、ジエチレングリコールジブチルエーテルのようなグリコールジアルキルエーテル類;
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、プロピレングリコールモノプロピルエーテルアセテート、メトキシブチルアセテート、メトキシペンチルアセテート、ジプロピレングリコールモノメチルエーテルアセテート、3−メチル−3−メトキシブチルアセテートのようなグリコールアルキルエーテルアセテート類;
ジエチルエーテル、ジプロピルエーテル、ジイソプロピルエーテル、ブチルエーテル、ジアミルエーテル、エチルイソブチルエーテル、ジヘキシルエーテルのようなエーテル類;
アセトン、メチルエチルケトン、メチルアミルケトン、メチルイソプロピルケトン、メチルイソアミルケトン、ジイソブチルケトン、メチルイソブチルケトン、シクロヘキサノン、エチルアミルケトン、メチルブチルケトン、メチルヘキシルケトン、メチルノニルケトンのようなケトン類;
エタノール、プロパノール、ブタノール、ヘキサノール、シクロヘキサノール、エチレングリコール、プロピレングリコール、ジエチレングリコール、ジプロピレングリコール、グリセリンのような1価又は多価アルコール類;
n−ペンタン、n−オクタン、ジイソブチレン、n−ヘキサン、ヘキセン、イソプレン、ジペンテン、ドデカンのような脂肪族炭化水素類;
シクロヘキサン、メチルシクロヘキサン、メチルシクロヘキセン、ビシクロヘキシルのような脂環式炭化水素類;
ベンゼン、トルエン、キシレン、クメンのような芳香族炭化水素類;
アミルホルメート、エチルホルメート、酢酸エチル、酢酸ブチル、酢酸プロピル、酢酸アミル、エチレングリコールアセテート、エチルプロピオネート、プロピルプロピオネート、酪酸ブチル、酪酸イソブチル、イソ酪酸メチル、エチルカプリレート、ブチルステアレート、エチルベンゾエート、3−エトキシプロピオン酸メチル、3−エトキシプロピオン酸エチル、3−メトキシプロピオン酸メチル、3−エトキシプロピオン酸エチル、3−メトキシプロピオン酸メチル、3−メトキシプロピオン酸エチル、3−メトキシプロピオン酸プロピル、3−メトキシプロピオン酸ブチル、γ−ブチロラクトンのような鎖状又は環状エステル類;
3−メトキシプロピオン酸、3−エトキシプロピオン酸のようなアルコキシカルボン酸類;
ブチルクロライド、アミルクロライドのようなハロゲン化炭化水素類;
メトキシメチルペンタノンのようなエーテルケトン類;
アセトニトリル、ベンゾニトリルのようなニトリル類。
本発明の着色感光性組成物中には前記した成分(1)〜(6)を必須成分として含有するが、該組成物の目的、用途等に応じて、改良のため以下の任意成分を混合することができる。
本発明に係る着色感光性組成物の感応感度を高める目的で、画像形成露光光源の波長に応じた増感色素を配合させることができる。
熱重合防止剤としては、例えば、ハイドロキノン、p−メトキシフェノール、ピロガロール、カテコール、2,6−t−ブチル−p−クレゾール、β−ナフトール等が用いられる。
可塑剤としては、例えば、ジオクチルフタレート、ジドデシルフタレート、トリエチレングリコールジカプリレート、ジメチルグリコールフタレート、トリクレジルホスフェート、ジオクチルアジペート、ジブチルセバケート、トリアセチルグリセリン等が用いられる。
<オ> 表面保護剤
<カ> 密着向上剤
<キ> 現像改良剤
<ク> 分散剤(分散助剤、界面活性剤)
<ケ> 塗布性改良剤
以下に本発明に係る着色感光性組成物の製造方法、及びこれを用いた本発明のカラーフィルターの製造方法の一例について説明する。
本発明の組成物を製造するには、まず色材を分散処理し、インクの状態に調整する。分散処理は、ペイントコンディショナー、サンドグラインダー、ボールミル、ロールミル、ストーンミル、ジェットミル、ホモジナイザー等を用いて行う。分散処理により色材が微粒子化するため、透過光の透過率向上及び塗布特性の向上が達成される。
本発明のカラーフィルターは、ブラックマトリクスが設けられた透明基板上に通常、赤、緑、青の画素画像を形成することにより製造することができる。
プロピレングリコールモノメチルエーテルアセテート57.0gと1−エトキシ−2−プロパノール57.0gを500mlの四つ口フラスコに入れ、窒素バブリングを行ないながら85℃まで昇温した。
イソブチルメタクリレート 23
メチルメタクリレート 37
メタクリル酸 20。
樹脂製造例1において、(3,4−エポキシシクロヘキシル)メチルメタクリレートの代わりに、等モル量の(3,4−エポキシシクロヘキシル)メチルアクリレートを使用した以外は、樹脂製造例1と同様にして光重合性高分子化合物Bを得た。
t−ブチルメタクリレート 23
メチルメタクリレート 37
メタクリル酸 20。
高分子化合物A(樹脂製造例1) 40部
青色色材(C.I.ピグメントブルー15:6) 40部
プロピレングリコールモノメチルエーテルアセテート 100部
これらを混合し、3本ロールミルで混練し、孔径5μmのフィルターで粗大粒子を濾過し、カラーフィルター用の青色顔料分散物とした。次いで、この顔料分散物を用いて、以下の成分を調合してカラーフィルター用光重合性組成物を得た。
ジペンタエリスリトールヘキサアクリレート 40部
高分子化合物A(樹脂製造例1) 80部
2-(2'-クロロフェニル)-4,5-ジフェニルイミダゾール2量体 8部
光重合開始剤(ミヒラーケトン) 20部
プロピレングリコールモノメチルエーテルアセテート 1000部
この組成物をカラーフィルター用のガラス基板にスピンコーターで塗布し、80℃で3分間乾燥させ、更に2.5kWの超高圧水銀灯を使用してマスクを介して100mJ/cm2の露光を行ない、0.04重量%水酸化カリウム水溶液に浸漬し、マスクパターン通りの画像を得た。画像を形成しない部分には顔料分散体を含むカラーレジストの残留物は認められなかった。また走査型顕微鏡で観察したところ表面の膜あれも見られなかった。
高分子化合物B(樹脂製造例2) 40部
青色色材(C.I.ピグメントブルー15:6) 40部
プロピレングリコールモノメチルエーテルアセテート 100部
これらを混合し、3本ロールミルで混練し、孔径5μmのフィルターで粗大粒子を濾過し、カラーフィルター用の青色顔料分散物とした。次いで、この顔料分散物を用いて、以下の成分を調合してカラーフィルター用光重合性組成物を得た。
ジペンタエリスリトールヘキサアクリレート 40部
高分子化合物B(樹脂製造例2) 80部
2-(2'-クロロフェニル)-4,5-ジフェニルイミダゾール2量体 8部
光重合開始剤(ミヒラーケトン) 20部
プロピレングリコールモノメチルエーテルアセテート 1000部
この組成物を実施例1と同様に塗布、乾燥、露光、現像し、マスクパターン通りの画像を得た。画像を形成しない部分には微量なカラーレジストの残留物が認められた。できあがった画像をSEM観察したところ、画像表面に凹凸が認められた。
青色色材(C.I.ピグメントブルー15:6)10.0部に高分子分散剤(ビッグケミカル社製BYK161。固形分濃度30重量%)33.4部及びプロピレングリコールモノメチルエーテルアセテート36.6部を加え、ペイントコンディショナーで8時間分散を行い、青色色材分散インキ5を得た。
青色色材(C.I.ピグメントブルー15:6)9.0部と銅フタロシアニン顔料(アビシア社製S−5000)1.0部の混合顔料を使用した以外は実施例2と同様にしてカラーフィルター用光重合性組成物を得た。以下、実施例1と同様にしてマスクパターン通りの画像を得た。画像を形成しない部分には顔料分散体を含むカラーレジストの残留物は認められなかった。また走査型顕微鏡で観察したところ表面の膜あれも見られなかった。
Claims (9)
- 不飽和二重結合を有する光重合性高分子化合物(1)、光重合開始剤(2)、アルカリ可溶性樹脂(3)、重合性モノマー又はオリゴマー(4)、色材(5)及び溶剤(6)を含むカラーフィルター用組成物において、前記不飽和二重結合を有する光重合性高分子化合物(1)及び前記アルカリ可溶性樹脂(3)がいずれも、下記一般式(I)及び(II)で表される繰り返し単位を有し、酸価が10〜300mgKOH/gの重合体であることを特徴とする着色感光性組成物。
- 前記一般式(I)において、R1が末端分岐状のアルキル基である請求項1〜3のいずれか1項に記載の着色感光性組成物。
- 前記一般式(I)及び(II)で表される繰り返し単位を有する重合体の重量平均分子量が5000以上である請求項1〜5のいずれか1項に記載の着色感光性組成物。
- 色材(5)及び溶剤(6)、場合によっては更に不飽和二重結合を有する光重合性高分子化合物(1)を含む色材分散組成物に、不飽和二重結合を有する光重合性高分子化合物(1)、光重合開始剤(2)、アルカリ可溶性樹脂(3)、重合性モノマー又はオリゴマー(4)及び溶剤(6)を混合して着色感光性組成物を製造する方法において、前記不飽和二重結合を有する光重合性高分子化合物(1)及び/又は前記アルカリ可溶性樹脂(3)として、下記一般式(I)及び(II)で表される繰り返し単位を有し、酸価が10〜300mgKOH/gの重合体を使用することを特徴とする着色感光性組成物の製造方法。
- 請求項1〜6のいずれか1項に記載の着色感光性組成物を用いて形成されたカラーフィルター。
- 請求項8に記載のカラーフィルターを用いて形成された液晶表示装置。
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