JP2022527945A - カラーフィルタ用の感光性樹脂組成物及びカラーフィルタ - Google Patents
カラーフィルタ用の感光性樹脂組成物及びカラーフィルタ Download PDFInfo
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Abstract
Description
(B)アルカリ可溶性樹脂と、
(C)重合性不飽和結合を少なくとも1つ有する化合物と、
(D)着色剤と、
(E)水素供与体と、
を含むカラーフィルタ用の感光性樹脂組成物であって、
光重合開始剤A1は、ヘキサアリールビスイミダゾール(即ち、HABI)類混合光開始剤であり、一般式(I)
[一般式(I)中、Ar1、Ar2、Ar3、Ar4、Ar5、Ar6は、同じであっても異なっていてもよく、それぞれ独立にして置換もしくは無置換のアリール基を表す。]
で示される構造を有し、その中、2-1’、2-3’、2’-1及び2’-3の4種類の結合部位のビスイミダゾール化合物を含有し、かつ、A1においてこれらの4種類の結合部位のビスイミダゾール化合物の合計含有量(質量%)が92%以上であり、
かつ、光重合開始剤は、i線(365nm)でのモル吸光係数が5000~10000の間である、カラーフィルタ用の感光性樹脂組成物。
光重合開始剤A1
前述した通り、本発明の光重合開始剤A1は、HABI類混合光開始剤であり、一般式(I)
[一般式(I)中、Ar1、Ar2、Ar3、Ar4、Ar5、Ar6は、同じであっても異なっていてもよく、それぞれ独立にして置換もしくは無置換のアリール基を表す。]
で示される構造を有し、その中、2-1’、2-3’、2’-1及び2’-3の4種類の結合部位のビスイミダゾール化合物を含有し、かつ、光重合開始剤A1においてこれらの4種類の結合部位のビスイミダゾール化合物の合計含有量(質量%)が92%以上であり、
かつ、光重合開始剤は、i線(365nm)でのモル吸光係数が5000~10000の間である。
一般式(I)中、前記アリール基は、好ましくはフェニル基である。
本発明の感光性樹脂組成物において、全量100質量部に対して、光重合開始剤A1の含有量は、0.1~10質量部であることが好ましい。
本発明に記載の感光性樹脂組成物における光重合開始剤としては、上記光重合開始剤A1以外に、少なくとも1種のオキシムエステル類光開始剤A2をさらに含有する。
本発明の感光性樹脂組成物において、アルカリ可溶性樹脂(B)の種類については特に制限されないが、耐熱性、現像性及び入手しやすさなどの観点から選択することが好適である。好ましくは、カルボキシ基、フェノール性水酸基などの酸性基を有するアルカリ可溶性樹脂であり、さらに好ましくはカルボキシ基含有共重合体であるアルカリ可溶性樹脂であり、特に好ましくはカルボキシ基を有するエチレン性不飽和モノマー[以下、「カルボキシ基含有不飽和モノマー」(P)と略称]とその他の共重合可能なエチレン性不飽和モノマー[以下、「共重合性不飽和モノマー」(Q)と略称する]の共重合体[以下、「カルボキシ基含有共重合体」(R)と略称する]である。
本発明において、上記した重合性不飽和結合を少なくとも1つ有する化合物(C)は、モノマー、オリゴマー、重合体などの化学的形態であってもよい。
本発明は、着色剤(D)の種類については特に制限されず、顔料と染料とを含んでもよい。
本発明の感光性樹脂組成物は、感光度を向上させるために水素供与体(E)をさらに含む。HABI類化合物は、光照射された後に解離し、生成したモノイミダゾールラジカル基は体積が大きく、立体障害により活性が低くなり、単独でモノマーの重合を発生させにくく、しかし、モノイミダゾールラジカル基は、水素供与体上の活性水素を奪いやすく、新しいリビングラジカル基を生じ、モノマーの重合を発生させる。
本発明の感光性樹脂組成物には、本分野で常用されるその他の助剤を選択的に添加してもよく、他の光開始剤及び/又は増感剤、有機溶剤、有機カルボン酸、顔料分散剤、接着促進剤、レベリング剤、現像性向上剤、酸化防止剤、熱重合禁止剤などを含む。なお、用途に応じて界面活性剤、蛍光増白剤、可塑剤、難燃剤、紫外線吸収剤、発泡剤、殺菌剤、帯電防止剤、磁性物質、導電材料、抗真菌性又は抗細菌材料、多孔質吸着剤、アロマ物質などをさらに添加してもよい。
前述した通り、本発明は、さらに、上記感光性樹脂組成物を用いたカラーフィルタ及びその製造方法に関する。
感光性樹脂層形成工程は、本発明の感光性樹脂組成物を支持体上に塗布し、感光性樹脂層を形成する工程である。
露光工程は、上記感光性樹脂層形成工程において形成された感光性樹脂層をマスクを介して露光する工程である。この過程では、光照射された塗布膜部分のみを硬化する。
露光工程に次いで、アルカリ性現像処理(現像工程)を行い、露光工程における未露光部分をアルカリ性水溶液に溶出させる。これにより、光硬化した部分だけが残る。
1.1 HABI類混合光開始剤a1の製造
窒素ガスの保護下で、1Lの4つ口フラスコに31.8gの2-(o-クロロフェニル)-4,5-ジフェニル-イミダゾール(M1)、51.3gの2,5-ビス(o-クロロフェニル)-4-(3,4-ジメトキシフェニル)-イミダゾール(M2)、4.2gの30%液状水酸化ナトリウム、4.0gのテトラブチルアンモニウムブロマイドおよび300gのトルエンを投入し、加熱しながら撹拌し、60~65℃になるときに85gの次亜塩素酸ナトリウム(11%の水溶液)を滴下し、滴下終了後、温度を維持しながら反応させ、サンプルを取ってHPLCによりインプロセス制御を行い、M1及びM2がいずれも1%未満となると、反応が完全となり、温度維持を終了した。温度維持しながらの反応が終了した後、100gの純水で4回洗浄し、その後、20gのトルエンで水層を1回抽出し、有機層に対して減圧蒸留を行った。蒸留して得られたものに70gのメタノールを添加し、完全溶解となるまで加熱しながら撹拌し、さらに、溶解液を30gのメタノールと50gの純水とで調製してなる溶液に滴下し、滴下終了後、ろ過、洗浄、乾燥を行い、79.1gの生成物a1を得た。
T1-2:2,2’-ビス(o-クロロフェニル)-4,4’,5,5’-テトラフェニル-2’,3-ビイミダゾール。
T2を合成モノイミダゾールM2は、非対称のモノイミダゾールに属し、M2にはM2-1及びM2-2の2種類の立体配置が存在し、構造式を以下に示す。
分離して得られた純粋T2に対して分析を行い、主構造が4つの結合部位の製品に対して、LCMSにより構造確認を行った。質量分析装置に付いたソフトウェアにより849と850分子のフラグメントピークを取得し、製品の分子量が848であり、T+1およびT+2に該当し、この4つの生成物は構造が類似し、分子量が同じであることが証明された。T2は、非対称のモノイミダゾールカップリングにより合成されたものであり、理論的には1-2と2-3結合部位が連結してなる主構造が8種類存在するが、ホモカップリングしたモノイミダゾールについて、構造における2’-1と2-1’の構造が同じであり、2’-3と2-3’の構造も同じであるので、T2にとって、実際には1-2と2-3結合部位が連結してなる主構造が4種類存在し、その組成はそれぞれ以下の通りである。
T2-2:2,2’,4,5’-テトラ(o-クロロフェニル)-4’,5-ビス(3,4-ジメトキシフェニル)-1,2’-ジイミダゾール
T2-3:2,2’,5,5’-テトラ(o-クロロフェニル)-4,4’-ビス(3,4-ジメトキシフェニル)-1,2’-ジイミダゾール
T2-4:2,2’,4,5’-テトラ(o-クロロフェニル)-4’,5-ビス(3,4-ジメトキシフェニル)-2’,3-ジイミダゾール。
T3-2:2,2’,5-トリス-(o-クロロフェニル)-4-(3,4-ジメトキシフェニル)-4’,5’-ジフェニル-2’,3-ジイミダゾール
T3-3:2,2’,5-トリス-(o-クロロフェニル)-4-(3,4-ジメトキシフェニル)-4’,5’-ジフェニル-2,3’-ジイミダゾール
T3-4:2,2’,5-トリス-(o-クロロフェニル)-4-(3,4-ジメトキシフェニル)-4’,5’-ジフェニル-1’,2-ジイミダゾール。
上記の実験分析をまとめて特定できるように、生成物a1は、T1(T1-1、T1-2)、T2(T2-1、T2-2、T2-3、T2-4)及びT3(T3-1、T3-2、T3-3、T3-4)により構成されたものであり、その中、2-1’、2-3’、2’-1及び2’-3の4種類の結合部位で構成されるビスイミダゾール化合物は、a1における含有量が92.5%である。
窒素ガスの保護下で、1Lの4つ口フラスコに50gの2-(4-クロロフェニル)-5-(6-クロロフェニル)-4-(3,4-ジメトキシフェニル)-イミダゾール(M3)、51gの2,5-ビス(o-クロロフェニル)-4-(3,4-ジメトキシフェニル)-イミダゾール(M2)、5.6gの30%液状水酸化ナトリウム、4.0gのテトラブチルアンモニウムブロマイド及び300gのトルエンを投入し、加熱しながら撹拌し、60~65℃になるときに90gの次亜塩素酸ナトリウム(11%の水溶液)を滴下し、滴下終了後、温度を維持しながら反応させ、サンプルを取ってHPLCによりインプロセス制御を行い、M2及びM3がいずれも1%未満となると、反応が完全となり、温度維持を終了した。温度維持しながらの反応が終了した後、100gの純水で4回洗浄し、その後、20gのトルエンで水層を1回抽出し、有機層に対して減圧蒸留を行った。蒸留して得られたマターに70gのメタノールを添加し、完全溶解となるまで加熱しながら撹拌し、さらに溶解液を30gのメタノールと50gの純水とで調製してなる溶液に滴下し、滴下終了後、洗浄、減圧乾燥、加熱乾燥を行い、98gの生成物a9を得た。
T4-2:2,2’-ビス(4-クロロフェニル)-4,5’-ビス(o-クロロフェニル)-4’,5-ビス(3,4-ジメトキシフェニル)-1,2’-ジイミダゾール
T4-3:2,2’-ビス(4-クロロフェニル)-5,5’-ビス(o-クロロフェニル)-4,4’-ビス(3,4-ジメトキシフェニル)-1,2’-ジイミダゾール
T4-4:2,2’-ビス(4-クロロフェニル)-4’,5-ビス(o-クロロフェニル)-4,5’-ビス(3,4-ジメトキシフェニル)-2,3’-ジイミダゾール。
LCMSにより構造を確認し、4つの構造のスペクトルが一致している。質量分析装置に付いたソフトウェアにより849及び850の分子フラグメントピークを得、製品の分子量が848であり、T+1及びT+2に一致しており、この4つの生成物のピーク構造が類似し、分子量が同じであることが証明された。
T5-2:2’-(4-クロロフェニル)-2,5,5’-トリス-(o-クロロフェニル)-4,4’-ビス(3,4-ジメトキシフェニル)-1,2’-ジイミダゾール
T5-3:2-(4-クロロフェニル)-2’,5,5’-トリス-(o-クロロフェニル)-4,4’-ビス(3,4-ジメトキシフェニル)-2’,3-ジイミダゾール
T5-4:2’-(4-クロロフェニル)-2,5,5’-トリス-(o-クロロフェニル)-4,4’-ビス(3,4-ジメトキシフェニル)-1’,2-ジイミダゾール。
LCMSにより構造を確認し、4つの構造のスペクトルが一致している。質量分析装置に付いたソフトウェアにより849及び850の分子フラグメントピークを得、製品の分子量が848であり、T+1及びT+2に一致しており、この4つの生成物はピーク構造が類似し、分子量が同じであることが証明された。
a17は、常州強力電子新材料股-有限公司により生産されるBCIMであり、その中に、2-1’、2-3’、2’-1及び2’-3の4種類の結合部位のビスイミダゾール化合物を含有し(対称構造であるので、2-1’と2’-1とは同一構造であり、2-3’と2’-3とは同一構造である)、かつ、A1においてこれらの4種類の結合部位のビスイミダゾール化合物の合計含有量(質量%)が99%であり、波長365nm(i線)におけるモル吸光係の数が26L×mol-1×cm-1である。それらの構造式を以下に示す。
2. 感光性樹脂組成物の製造
表2-1、2-2に示す配合成分を参照して、各成分を均一に混合して感光性樹脂組成物を製造した。特に説明がない限り、表に示す部数がいずれも質量部である。
3.1 輝度
各実施例及び比較例において製造した感光性樹脂組成物に対して、スピンコート法を用い、上記得られた感光性樹脂組成物をガラス(#1737、コーニング社製)上に塗布し、その後、100℃で3分間かけて揮発成分を揮発させて感光性樹脂層を形成した。冷却後、超高圧水銀灯を用いて当該感光性樹脂層を露光し、照射光量を100mJ/cm2とした。次いで、230℃で20分間ポストベークを行い、膜厚が2μmの着色層を有するガラス基板を得た。オリンパス(Olympus)製の顕微分光測定装置OSP-SP200を用いて、着色層を有するガラス基板の色度を測定し、C光源でx=0.29、y=0.59の色度のときのY値を測定した。Y値が高ければ高いほど、液晶表示装置用のカラーフィルタがより良好な性能を示す。
各実施例及び比較例において製造した感光性樹脂組成物に対して、スピンコート法を用い、上記得られた感光性樹脂組成物をガラス(#1737,コーニング社製)上に塗布し、その後、100℃で3分間かけて揮発成分を揮発させて感光性樹脂層を形成した。冷却後、i線縮小投影露光装置により、365nmの波長で、縦20μm×横20μmのマスクで露光量が50mJ/cm2となるように塗布膜を照射した。照射後、現像液(商品名:CD-2000、60%、富士フイルムエレクトロニクスマテリアルズ製)を用いて、塗布膜を23℃で60秒現像した。次いで、流れ水で20秒洗浄した後、噴射乾燥を行ってパターン画像を得た。画像形成は、光学顕微鏡により確認された。得られた画素パターンの幅が大きいものは、高感光度であるので好ましい。下記の判定基準に準じて得られた画素パターンの幅を判定し、判定基準は以下の通りである。
各実施例及び比較例で製造した感光性樹脂組成物に対して、スピンコーダーを利用して液状組成物をガラス基板上に塗布し、その後、100℃で5min乾燥して溶剤を除去し、膜厚10μmの塗膜を形成した。上記厚さの塗膜を得るために、塗布過程は、一回で完成してもよいし、複数回に分けて行ってもよい。塗膜付きの基板を室温まで冷却し、マスクプレートを付けて、高圧水銀灯を備えたRW-UV.70201クローラ露光機により、照射波長を250~450nmとし、一回露光で受けたエネルギーを約80mJ/cm2とし、マスクプレートの隙間を介して紫外線照射で塗膜を露光した。25℃の温度で、1%のNaOH水溶液現像を用い、さらに超純水で洗浄し、風乾した。最後に、240℃のオーブン中で30minポストベークし、マスク板が遷移したパターンを得た。
3.3で得られたパターンを対象とし、GB9286-88「塗料およびワニス-塗膜のクロスカット試験」を参照して、クロスカット試験方法により塗膜の密着性を評価した。破壊程度に応じて0~5級(合計6級)に分けて、その中、0級が一番良く、膜表面に全く格子が脱落しない。5級が極めて悪く、膜表面にひどい剥離が発生した。
Claims (14)
- (A)光重合開始剤A1及び少なくとも1種のオキシムエステル類光開始剤A2を含む光重合開始剤と、
(B)アルカリ可溶性樹脂と、
(C)重合性不飽和結合を少なくとも1つ有する化合物と、
(D)着色剤と、
(E)水素供与体と、
を含むカラーフィルタ用の感光性樹脂組成物であって、
光重合開始剤A1は、ヘキサアリールビスイミダゾール類混合光開始剤であり、一般式(I)
[一般式(I)中、Ar1、Ar2、Ar3、Ar4、Ar5、Ar6は、同じであっても異なっていてもよく、それぞれ独立にして置換もしくは無置換のアリール基を表す。]
で示される構造を有し、その中、2-1’、2-3’、2’-1及び2’-3の4種類の結合部位のビスイミダゾール化合物を含有し、かつ、A1においてこれらの4種類の結合部位のビスイミダゾール化合物の合計含有量(質量%)が92%以上であり、
かつ、光重合開始剤は、i線(365nm)でのモル吸光係数が5000~10000の間であるカラーフィルタ用の感光性樹脂組成物。 - 組成物において、光重合開始剤A1とオキシムエステル類光開始剤A2との質量比が1:5~5:5であることを特徴とする請求項1に記載の組成物。
- Ar1、Ar2、Ar3、Ar4、Ar5、Ar6は、同じであっても異なっていてもよく、それぞれ独立にして置換もしくは無置換のアリール基を表し、かつ、前記アリール基は、フェニル基であることを特徴とする請求項1に記載の組成物。
- アリール基上の置換基は、ハロゲン元素、ニトロ基、シアノ基、アミノ基、ヒドロキシ基、C1~C20のアルキル基またはアルケニル基、C1~C8のアルコキシ基であり、その中、各独立変数(即ち、各置換基)におけるメチレン基は、任意に酸素、硫黄、イミノ基により置換されていてもよいことを特徴とする請求項1~3のいずれか1項に記載の組成物。
- アリール基上の置換基は、フッ素、塩素、臭素、ニトロ基、シアノ基、アミノ基、ヒドロキシ基、C1~C10のアルキル基またはアルケニル基、C1~C5のアルコキシ基であり、その中、各独立変数におけるメチレン基は、任意に酸素、硫黄、イミノ基により置換されていてもよいことを特徴とする請求項1~3のいずれか1項に記載の組成物。
- Ar1、Ar2、Ar3、Ar4、Ar5、Ar6のうちの少なくとも1つは、ハロゲン元素置換基を含有するアリール基であり、ハロゲン元素置換基は、塩素であることが好ましいことを特徴とする請求項1~3のいずれか1項に記載の組成物。
- 光重合開始剤A1は、一般式(I)で示される構造を満足する2-1’、2-3’、2’-1及び2’-3の4種類の結合部位のビスイミダゾール化合物の合計含有量(質量%)が95%以上であり、好ましくは一般式(I)で示される構造を満足する2-1’、2-3’、2’-1及び2’-3の4種類の結合部位のビスイミダゾール化合物からなることを特徴とする請求項1~3のいずれか1項に記載の組成物。
- アルカリ可溶性樹脂(B)は、カルボキシ基含有共重合体であるアルカリ可溶性樹脂であり、好ましくはカルボキシ基を有するエチレン性不飽和モノマーとその他の共重合可能なエチレン性不飽和モノマーとの共重合体であることを特徴とする請求項1に記載の組成物。
- 重合性不飽和結合を少なくとも1つ有する化合物(C)は、アクリレート類化合物及びメタクリレート類化合物から選ばれる少なくとも1種であることを特徴とする請求項1に記載の組成物。
- 着色剤(D)は、顔料及び/又は染料から選ばれることを特徴とする請求項1に記載の組成物。
- 水素供与体(E)は、アミン類化合物、カルボン酸類化合物、メルカプト基含有有機硫黄化合物及びアルコール類化合物のうちの少なくとも1種であることを特徴とする請求項1に記載の組成物。
- 請求項1~11のいずれか1項に記載の感光性樹脂組成物を用いて形成された着色パターンを支持体上に有することを特徴とするカラーフィルタ。
- 請求項1~11のいずれか1項に記載の感光性樹脂組成物を支持体上に塗布して感光性樹脂層を形成する工程と、マスクを介して感光性樹脂層を露光する工程と、露光後の感光性樹脂層を現像して着色パターンを形成する工程と、を含むカラーフィルタの製造方法。
- 形成された着色パターンを加熱及び/又は露光によりさらに硬化する後硬化工程をさらに含むことを特徴とする請求項13に記載の製造方法。
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