JP2007249113A - スペーサー用感放射線性樹脂組成物、スペーサーおよび液晶表示素子 - Google Patents
スペーサー用感放射線性樹脂組成物、スペーサーおよび液晶表示素子 Download PDFInfo
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- JP2007249113A JP2007249113A JP2006076080A JP2006076080A JP2007249113A JP 2007249113 A JP2007249113 A JP 2007249113A JP 2006076080 A JP2006076080 A JP 2006076080A JP 2006076080 A JP2006076080 A JP 2006076080A JP 2007249113 A JP2007249113 A JP 2007249113A
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- 235000019795 sodium metasilicate Nutrition 0.000 description 1
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- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
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- 229910001887 tin oxide Inorganic materials 0.000 description 1
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- 229910052721 tungsten Inorganic materials 0.000 description 1
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- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
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Landscapes
- Liquid Crystal (AREA)
- Materials For Photolithography (AREA)
Abstract
【解決手段】(A)カーボンブラックに代表される導電性粒子、(B)アルカリ可溶性樹脂、(C)エチレン性不飽和結合を有する重合性化合物、および(D)光重合開始剤を含有することを特徴とするスペーサー用感放射線性樹脂組成物によって達成される。
【選択図】なし
Description
そこで、これらの問題を解決するために、スペーサーをフォトリソグラフィーにより形成する方法が採用されるようになってきた。この方法は、感光性樹脂組成物を基板上に塗布し、所定のマスクを介して紫外線を露光したのち現像して、ドット状やストライプ状のスペーサーを形成するものであり、画素形成領域以外の所定の場所にのみスペーサーを形成することができるため、前述したような問題は基本的には解決される(特許文献1)。
最近のカラー液晶表示素子は、従来に比べて厳密な寸法精度を要求され、僅かなギャップムラも表示不良の原因となっている。また、表示パネルとしたときの焼き付きや表示ムラなどのような表示性能への悪影響が問題となっており、このような悪影響を回避できるスペーサー材料が強く望まれている。さらには、十分な耐熱性、耐薬品性、強度、密着性を併せ持ち、かつ、表示性能を劣化させないスペーサーを形成する感放射線性樹脂組成物が求められ、これらを十分に満足するものは未だ提案されていない。
本発明における導電性粒子は、感放射線性組成物の抵抗値を下げるためのものであり、その例としては、カーボンブラック、金属粒子、金属酸化物粒子等を挙げることができ、中でもカーボンブラックが好ましい。
前記カーボンブラックとしては、例えば、SAF、SAF−HS、ISAF、ISAF−LS、ISAF−HS、HAF、HAF−LS、HAF−HS、NAF、FEF、FEF−HS、SRF、SRF−LM、SRF−LS、GPF、ECF、N−339、N−351等のファーネスブラック;FT、MT等のサーマルブラック;アセチレンブラック等を挙げることができる。
界面活性剤の使用量は、導電性粒子100重量部に対して、通常、50重量部以下、好ましくは0〜30重量部である。
本発明におけるアルカリ可溶性樹脂としては、(A)導電性粒子に対してバインダーとして作用し、かつスペーサーを形成する際に用いられる現像液、特に好ましくはアルカリ現像液に可溶性である限り、適宜の樹脂を使用することができる。
これらの他の不飽和単量体は、単独でまたは2種以上を混合して使用することができる。
不飽和イソシアナート化合物(α)としては、例えば、2−(メタ)アクリロイルオキシエチルイソシアネート、3−(メタ)アクリロイルオキシプロピルイソシアネート、4−(メタ)アクリロイルオキシブチルイソシアネート、6−(メタ)アクリロイルオキシヘキシルイソシアネート、8−(メタ)アクリロイルオキシオクチルイソシアネート、10−(メタ)アクリロイルオキシデシルイソシアネートの如き(メタ)アクリル酸誘導体を挙げることができる。
これらの不飽和イソシアナート化合物(α)のうち、共重合体〔A〕との反応性の点から、2−アクリロイルオキシエチルイソシアネート、2−メタクリロイルオキシエチルイソシアネート等が好ましい。
上記不飽和イソシアナート化合物(α)は、単独でまたは2種以上を混合して使用することができる。
また、不飽和カルボン酸ヒドロキシアルキルエステル類を含むカルボキシル含有共重合体と不飽和イソシアナート化合物(α)との反応は、例えば、ジラウリン酸ジ−n−ブチルすず(IV)等の触媒やp−メトキシフェノール等の重合禁止剤を含有する不飽和カルボン酸ヒドロキシアルキルエステル類を含むカルボキシル含有共重合体溶液に、室温または加温下で、攪拌しつつ、不飽和イソシアナート化合物(α)を投入することによって実施することもできる。
上記において、不飽和イソシアナート化合物(α)の使用量は、不飽和カルボン酸ヒドロキシアルキルエステル類を含むカルボキシル含有共重合体中の不飽和カルボン酸ヒドロキシアルキルエステル類に対して、好ましくは0.1〜90重量%、さらに好ましくは10〜80重量%、特に好ましくは 25〜75重量%である。不飽和イソシアナート化合物(α)の使用量が0.1重量%未満では、感度ならびに弾性特性向上への効果が小さく、一方90重量%を超えると、未反応の不飽和イソシアナート化合物(α)が残存し、得られる重合体溶液や感放射線性樹脂組成物の保存安定性が低下する傾向がある。
本発明で用いられる(C)エチレン性不飽和結合を有する重合性化合物[B]としては、重合性が良好であり、得られるスペーサーの強度が向上する点から、エポキシ基を持たず且つ単官能、2官能または3官能以上の(メタ)アクリレートが好ましく、2官能または3官能以上の(メタ)アクリレートがとくに好ましく用いられる。
本発明における光重合開始剤とは、放射線の照射(以下、「露光」という。)により分解または結合の開裂を生じ、ラジカル、アニオン、カチオン等の、前記(C)多官能性モノマーや場合により使用される単官能性モノマーの重合を開始することができる活性種を発生する化合物を意味する。
さらに、スペーサー用感放射線性組成物には、必要に応じて、種々の添加剤を配合することもできる。
このような添加剤としては、例えば、銅フタロシアニン誘導体等の青色顔料誘導体や黄色顔料誘導体等の分散助剤;ポリビニルアルコール、ポリエチレングリコールモノアルキルエーテル類、ポリ(フロロアルキルアクリレート)類等の高分子化合物;ノニオン系、カチオン系、アニオン系等の界面活性剤;ビニルトリメトキシシラン、ビニルトリエトキシシラン、ビニルトリス(2−メトキシエトキシ)シラン、N−(2−アミノエチル)−3−アミノプロピルメチルジメトキシシラン、N−(2−アミノエチル)−3−アミノプロピルトリメトキシシラン、3−アミノプロピルトリエトキシシラン、3−グリシドキシプロピルトリメトキシシラン、3−グリシドキシプロピルメチルジメトキシシラン、2−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、3−クロロプロピルメチルジメトキシシラン、3−クロロプロピルトリメトキシシラン、3−メタクリロキシプロピルトリメトキシシラン、3−メルカプトプロピルトリメトキシシラン等の密着促進剤;2,2−チオビス(4−メチル−6−t−ブチルフェノール)、2,6−ジ−t−ブチルフェノール等の酸化防止剤;2−(3−t−ブチル−5−メチル−2−ヒドロキシフェニル)−5−クロロベンゾトリアゾール、アルコキシベンゾフェノン類等の紫外線吸収剤;ポリアクリル酸ナトリウム等の凝集防止剤等を挙げることができる。
スペーサー用感放射線性組成物(α)は、前記(A)導電性粒子、(B)アルカリ可溶性樹脂、(C)多官能性モノマーおよび(D)光重合開始剤を必須の成分とし、場合によりさらに前記添加剤を含有するが、通常、適当な溶媒に(A)成分を分散させるとともに、(A)成分以外の各成分を溶解させた液状組成物として調製される。
前記溶媒としては、(A)〜(D)各成分と反応せず、適度の揮発性を有するものである限り、適宜に選択して使用することができる。
次に、本発明のスペーサー用感放射線性樹脂組成物を用いて、本発明のスペーサーを形成する方法について詳述する。基板表面に本発明の感放射性樹脂組成物を塗布し、加熱により溶媒を除去することによって、塗膜が形成される。基板表面への感放射性樹脂組成物の塗布方法としては、例えばスプレー法、ロールコート法、回転塗布法などの各種の方法を採用することができる。
合成例1
冷却管および攪拌機を備えたフラスコに、2,2’−アゾビス(2,4−ジメチルバレロニトリル)1部およ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200部を仕込み、引き続きメタクリル酸15部、スチレン15部、ベンジルメタクリレート35部、グリセロールモノメタクリレート10部、N−フェニルマレイミド25部および連鎖移動剤α−メチルスチレンダイマー2.5部を仕込んで窒素置換したのち、ゆるやかに撹拌して、反応溶液を80℃に昇温し、この温度を保持して3時間重合した。その後、反応溶液を100℃に昇温して、2,2’−アゾビス(2,4−ジメチルバレロニトリル)0.5部を加え、さらに1時間重合することにより、樹脂溶液(固形分濃度=33.0%)を得た。
得られた樹脂は、Mw=17,000、Mn=8,000であった。この樹脂を「樹脂(B−1) 」とする。
冷却管、撹拌機を備えたフラスコに、2,2'−アゾビス(2,4−ジメチルバレロニトリル)7重量部、ジエチレングリコールメチルエチルエーテル200重量部を仕込んだ。引き続きスチレン5重量部、メタクリル酸16重量部、ジシクロペンタニルメタクリレート34重量部、メタクリル酸グリシジル40重量部、α−メチルスチレンダイマー3重量部を仕込み窒素置換した後、さらに1,3−ブタジエンを5重量部仕込みゆるやかに攪拌を始めた。溶液の温度を70℃に上昇させ、この温度を5時間保持し共重合体[A−2]を含む重合体溶液を得た。得られた重合体溶液の固形分濃度は33.1%であり、重合体の重量平均分子量は、10,000であった。
合成例3
冷却管、撹拌機を備えたフラスコに、2,2’−アゾビスイソブチロニトリル5部、酢酸3-メトキシブチル250部を仕込み、引き続いてメタクリル酸18部、メタクリル酸トリシクロ[ 5.2.1.02,6 ] デカン−8−イル30部、スチレン5部、ブタジエン5部、メタクリル酸6−ヒドロキシヘキシルエステル25部、メタクリル酸テトラヒドロフラン−2−イル17部を仕込んで、窒素置換したのち、緩やかに攪拌しつつ、溶液の温度を80℃に上昇させ、この温度を4時間保持し、その後100℃に上昇させ、この温度を1時間保持して重合することにより、固形分濃度27.5%の共重合体〔α−1〕溶液を得た。
得られた共重合体〔α−1〕について、MwをGPC(ゲルパーミエイションクロマトグラフィー) HLC−8020(商品名、東ソー(株)製)を用いて測定したところ、14,000であった。
次いで、前記共重合体〔α−1〕溶液に、2−メタクリロイルオキシエチルイソシアネート(商品名カレンズMOI、昭和電工(株)製)14部、4−メトキシフェノール0.08部を添加したのち、60℃で2時間攪拌して反応させた。2−メタクリロイルオキシエチルイソシアネート由来のイソシアネート基と共重合体〔α−1〕の水酸基の反応の進行は、IR(赤外線吸収)スペクトルにより確認した。重合体溶液〔α−1〕、60℃で1時間反応後の溶液および2時間反応後の溶液それぞれのIRスペクトルをそれぞれ図3の(a)、(b)および(c)に示す。反応の進行とともに2−メタクリロイルオキシエチルイソシアネートのイソシアネート基に由来する2,270cm−1付近のピークが減少している様子を確認した。固形分濃度30.5%の〔A〕重合体溶液を得た。この〔A〕重合体を、重合体(A−1)とする。
合成例4
冷却管、撹拌機を備えたフラスコに、2,2’−アゾビス(2,4−ジメチルバレロニトリル)7重量部、プロピレングリコールモノメチルエーテルアセテート200重量部を仕込んだ。引き続きスチレン20重量部、メタクリル酸16重量部、メタクリル酸トリシクロ[ 5.2.1.02,6]デカン−8−イル18重量部、3−(メタクリロイルオキシメチル)−3−エチルオキセタン40重量部を仕込み窒素置換した後、ゆるやかに攪拌を始めた。溶液の温度を70℃に上昇させ、この温度を5時間保持し共重合体[A−1]を含む重合体溶液を得た。得られた重合体溶液の固形分濃度は33.0%であり、重合体の重量平均分子量は、24,000であった(重量平均分子量はGPC(ゲルパーミエイションクロマトグラフィー) HLC−8020(東ソー(株)製)を用いて測定したポリスチレン換算分子量である)。
(A)導電性粒子としてカーボンブラック(電気抵抗値:102 Ω・cm)10重量部と、(B)アルカリ可溶性樹脂として合成例1の共重合体50重量部、(C)多官能性モノマーとしてジペンタエリスリトールヘキサアクリレート40重量部、(D)光重合開始剤として2,2'−ビス(2−クロロフェニル)−4,4',5,5'−テトラキス(4−エトキシカルボニルフェニル)−1,2'−ビイミダゾール10重量部、4,4'−ビス(ジエチルアミノ)ベンゾフェノン10重量部および2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)ブタン−1−オン20重量部、溶媒として3−エトキシプロピオン酸エチル1500重量部を混合して、感放射線性組成物の液状組成物(S−1)を調製した。
ガラス基板上にスピンナーを用いて、上記組成物(S−1)を塗布した後、90℃で3分間ホットプレート上でプレベークして膜厚各5.8μmの塗膜を形成した。上記で得られた塗膜に10μm角の残しパターンのマスクを介して、365nmでの強度が300W/m2である紫外線を10秒間照射した。この際の紫外線照射は酸素雰囲気下(空気中)で行った。次いでテトラメチルアンモニウムヒドロキシド0.1重量%水溶液で25℃で90秒間現像した後、純水で1分間流水洗浄した。上記で形成されたスペーサーをオーブン中で220℃で60分間加熱し硬化させ、膜厚5μmのスペーサーを得た。
また別途、この感放射線性組成物の液状組成物を用いて硬化物を形成して電気抵抗値を測定したところ、108 Ω・cmであった。
実施例1において、合成例2の樹脂を用いた以外は実施例1に従い膜厚5μmのスペーサーを得た。得られた基板には、未露光部の基板上に残渣が認められず、またスペーサーの剥がれ、欠落および欠損も認められず、しかも高い膜硬度を有していた。さらに、この基板を使用して液晶パネルを作製したところ、焼き付きや表示ムラなどの表示不良は認められなかった。
また別途、この感放射線性組成物の液状組成物を用いて硬化物を形成して電気抵抗値を測定したところ、108 Ω・cmであった。
実施例1において、合成例3の樹脂を用いた以外は実施例1に従い膜厚5μmのスペーサーを得た。得られた基板には、未露光部の基板上に残渣が認められず、またスペーサーの剥がれ、欠落および欠損も認められず、しかも高い膜硬度を有していた。さらに、この基板を使用して液晶パネルを作製したところ、焼き付きや表示ムラなどの表示不良は認められなかった。
また別途、この感放射線性組成物の液状組成物を用いて硬化物を形成して電気抵抗値を測定したところ、108 Ω・cmであった。
実施例1において、合成例4の樹脂を用いた以外は実施例1に従い膜厚5μmのスペーサーを得た。得られた基板には、未露光部の基板上に残渣が認められず、またスペーサーの剥がれ、欠落および欠損も認められず、しかも高い膜硬度を有していた。さらに、この基板を使用して液晶パネルを作製したところ、焼き付きや表示ムラなどの表示不良は認められなかった。
また別途、この感放射線性組成物の液状組成物を用いて硬化物を形成して電気抵抗値を測定したところ、108 Ω・cmであった。
(A)導電性粒子を使用しなかったこと以外は、実施例1と同様にして、感放射線性組成物の液状組成物を調製して、基板上にスペーサーを形成した。
Claims (7)
- 硬化物の電気抵抗値が1012Ω・cm以下であることを特徴とするスペーサー用感放射線性樹脂組成物。
- (A)導電性粒子、(B)アルカリ可溶性樹脂、(C)エチレン性不飽和結合を有する重合性化合物、および(D)光重合開始剤を含有することを特徴とする請求項1に記載のスペーサー用感放射線性樹脂組成物。
- (A)導電性粒子がカーボンブラックを含む請求項1〜2に記載のスペーサー用感放射線性樹脂組成物。
- (A)導電性粒子の含有量が、全固形分の0.1〜30重量%である1〜3に記載のスペーサー用感放射線性樹脂組成物。
- 請求項1〜4に記載の感放射線性樹脂組成物から形成されてなる液晶表示素子用スペーサー
- 少なくとも以下の工程を以下に記載の順序で含むことを特徴とする液晶表示素子用スペーサーの形成方法。
(イ)請求項1〜4に記載の感放射線性樹脂組成物の被膜を基板上に形成する工程、
(ロ)該被膜の少なくとも一部に露光する工程、
(ハ)露光後の該被膜を現像する工程、および
(ニ)現像後の該被覆膜を加熱する工程。 - 請求項5に記載のスペーサーを具備する液晶表示素子。
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JP2010044365A (ja) * | 2008-07-17 | 2010-02-25 | Jsr Corp | 着色層形成用感放射線性組成物、カラーフィルタおよびカラー液晶表示素子 |
JP2011099918A (ja) * | 2009-11-04 | 2011-05-19 | Sumitomo Chemical Co Ltd | 着色感光性樹脂組成物、塗膜、パターン及び表示装置 |
JP2013134264A (ja) * | 2011-12-22 | 2013-07-08 | Tokyo Ohka Kogyo Co Ltd | ブラックカラムスペーサ用感光性樹脂組成物、ブラックカラムスペーサ、表示装置、及びブラックカラムスペーサの形成方法 |
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JP2008197613A (ja) * | 2007-01-15 | 2008-08-28 | Fujifilm Corp | 硬化性組成物、これを用いたカラーフィルタ及びその製造方法、並びに固体撮像素子 |
US8778575B2 (en) | 2007-01-15 | 2014-07-15 | Fujifilm Corporation | Curable composition, color filter using the same and manufacturing method therefor, and solid image pickup element |
JP2010044365A (ja) * | 2008-07-17 | 2010-02-25 | Jsr Corp | 着色層形成用感放射線性組成物、カラーフィルタおよびカラー液晶表示素子 |
JP2011099918A (ja) * | 2009-11-04 | 2011-05-19 | Sumitomo Chemical Co Ltd | 着色感光性樹脂組成物、塗膜、パターン及び表示装置 |
JP2013134264A (ja) * | 2011-12-22 | 2013-07-08 | Tokyo Ohka Kogyo Co Ltd | ブラックカラムスペーサ用感光性樹脂組成物、ブラックカラムスペーサ、表示装置、及びブラックカラムスペーサの形成方法 |
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