JP6556743B2 - 液晶シーリング用の硬化性樹脂組成物 - Google Patents
液晶シーリング用の硬化性樹脂組成物 Download PDFInfo
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- JP6556743B2 JP6556743B2 JP2016552994A JP2016552994A JP6556743B2 JP 6556743 B2 JP6556743 B2 JP 6556743B2 JP 2016552994 A JP2016552994 A JP 2016552994A JP 2016552994 A JP2016552994 A JP 2016552994A JP 6556743 B2 JP6556743 B2 JP 6556743B2
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Description
a)
からなる群から選択されるマレイミド樹脂;
b)有機過酸化物および有機アゾ化合物からなる群から選択される熱フリーラジカル開始剤;
c)エポキシ樹脂;および
d)潜伏性エポキシ硬化剤
を含む硬化性樹脂組成物を提供する。
1)第1基材の表面の周縁のシーリング領域に本発明の硬化性樹脂組成物を適用するステップ;2)第1基材の表面の該シーリング領域で取り囲まれた中央領域に液晶を滴下するステップ;3)第1基材上に第2基材を重ねるステップ;4)UV硬化ステップ;および5)熱硬化ステップ。
本発明の液晶シーリング用硬化性樹脂組成物は、特定のマレイミド樹脂を含む。
nは1〜3であり、Xlは脂肪族または芳香族基である。]
を有する。Xlの群の例としては、ポリ(ブタジエン)、ポリ(カーボネート)、ポリ(ウレタン)、ポリ(エーテル)、ポリ(エステル)、単純な炭化水素、および、カルボニル、カルボキシル、アミド、カーバメート、尿素、エステル、またはエーテルなどの官能基を含有する単純な炭化水素が挙げられる。
本発明の液晶シーリング用硬化性樹脂組成物は熱フリーラジカル開始剤を含む。
接着強度および信頼性を含むシーリング性能をさらに高めるために、硬化性樹脂組成物中でエポキシ樹脂を使用する。本発明のエポキシ樹脂成分は、任意の通常のエポキシ樹脂、以下に限定はされないが、芳香族グリシジルエーテル、脂肪族グリシジルエーテル、脂肪族グリシジルエステル、環状脂肪族グリシジルエーテル、環状脂肪族グリシジルエステル、環状脂肪族エポキシ樹脂およびそれらの混合物を含んでよい。
潜伏性エポキシ硬化剤は、熱を与える際にエポキシ樹脂部分を硬化させるために使用される。適当な潜伏性エポキシ硬化剤は、市販され入手可能な潜伏性エポキシ硬化剤から得ることができ、単独で、または、2種以上の潜伏性エポキシ硬化剤を組み合わせて使用することができる。
本発明の硬化性樹脂組成物は任意に、必要に応じて、光重合反応を可能にするさらなる成分、例えばビニルエーテル化合物または(メタ)アクリレート化合物を含有し得る。さらに、本発明の硬化性樹脂組成物は、流動性、分配または印刷特性、貯蔵特性、硬化特性および硬化後の物理的特性などの特性を改善または変更するために、添加剤、樹脂成分などをさらに含んでよい。
(a)第1基材の表面の周縁のシーリング領域に、本発明の硬化性樹脂組成物を適用するステップ;
(b)第1基材の表面の該シーリング領域で取り囲まれた中央領域に液晶を滴下するステップ;
(c)第1基材上に第2基材を重ねるステップ;
(d)該硬化性組成物のUV照射による一時的固定を行うステップ、および
(e)該硬化性組成物の加熱による最終固定を行うステップ。
EPICLON 850S、ビスフェノールA型エポキシ樹脂、Dainippon Ink & Chemicals、Inc.製。
Epikote1007、ビスフェノールAおよびエピクロロヒドリンから製造、融点=103-115℃、分子量2870、Momentive Specialty Chemicals Inc.製。
DER661、ビスフェノールAおよびエピクロロヒドリンから製造、融点=75-85℃;分子量1050、Dow Chemical製。
EH-4357S、変性アミン、ADEKA社製、さらに粉砕された微細粉末。
HX3932HP、マイクロカプセル型イミダゾール、旭化成株式会社製。
Ebecryl 3700、ビスフェノールA系エポキシのアクリレートエステル、Cytec Industries Inc.製。
Irgacure 651、BASF製。
SO-E2、シリカ、平均粒子サイズ0.5μm、Admatechs Co. Ltd.製。
ZEFIAC F351、アクリル酸ブチル-メタクリル酸-メタクリル酸メチルコポリマー、平均粒子サイズ0.3μm、Ganz Chemical Co.,Ltd.製。
Aerosil R805、Evonik Industries製。
粘度および粘度安定性
樹脂組成物の25℃での初期粘度をレオメーター(TA、AR2000 ex)を15s-1の剪断速度で用いて測定した。不透明なポリエチレン容器に10gの樹脂組成物を入れて、しっかりと密閉し、25℃で7日間の貯蔵後に、15s-1の剪断速度での粘度値を再測定した。該初期粘度および7日後の粘度増加(対初期粘度)を表2に示す。25%未満の粘度増加割合は貯蔵安定性が良好であることを表すが、25%以上の場合は貯蔵安定性が乏しいことを表す。
組成物全体の1重量%の5μmスペーサーを樹脂組成物中に添加し、50mm×50mm×0.7mmのITO(酸化インジウム錫)ガラス上に(Asymtekを用いて)分注し、長さ20mm、直径約0.7mmをそれぞれ有する2つの交差線(図1参照)を形成させた。同様の対ITOガラスを逆に重ねてこれらに接合させ、荷重下にて固定させ、光硬化を紫外線(UV)照射装置(Fusion UV、Dランプを備える)を用いて3000mJ/cm2の照射エネルギーで行い固定させ、次いで、該試験片を、120℃のオーブン中、60分の熱処理に付した。得られた試験片を型内のトップガラスに固定し、金属カラム(図1に示すように、2mmの直径を有する)でガラスの下を1.27mm/sの加圧速度(Instron試験機を用いる)でプレスすることにより試験した。最も高いプレス強度値を記録し、ライン幅をプレス強度で割ったものを接着強度(N/mm)と称した。
接着試験片を上記と同様の方法で製造し、60℃の温度および90%の湿度の高温高質チャンバーに5日(120時間)貯蔵し、次いで、上記と同様の試験方法を用いて接着強度を試験した。50%より高い、高温高質貯蔵前の接着強度に対する接着強度の維持割合は、高温高質貯蔵後の接着信頼性が良好であることを表し、50%未満の維持率は、高温高質貯蔵後の接着信頼性に乏しいことを表す。
樹脂組成物1グラムを1mm厚のガラスプレートに適用し、約4mmの直径を有するドーム形状を形成し、試験片を作製した。該試験片に、3000mJ/cm2のUVライト(Fusion UVによる、Dランプを備える)を照射し、次いで120℃のオーブンで60分間熱処理した(UVおよび熱サンプルとして記録)。比較として、同様の樹脂組成物を有する該試験片を120℃で60分間の熱によってのみ硬化させた(熱サンプルとして記録)。硬化プロセスの前後において、該試験片をFT-IR分光法により解析した。マレイド樹脂またはアクリレート樹脂(比較例1においてのみ)中のC=Cの反応割合を、マレイミド(690cm-1)またはアクリル基(1405cm-1)に帰属されるピーク面積および参照ピーク面積(2950cm-1)から計算した。
組成物全体の1重量%の5μmスペーサーを樹脂組成物に添加した。次いで、得られた組成物の2mgを(Asymtekを用いて)ガラス基材(20mm×70mm)の表面の周縁に長方形に分注させた。その後、7mgの液晶をシーリング領域で取り囲まれた中央領域に滴下し、真空下で脱気し、続いて該第1基材上に第2ガラス基材を重ねた。2つのガラス基材を付着後、真空を解除して試験片を得た。次いで、該試験片に3000mJ/cm2のUVライトを照射した(Dランプを備えるFusion UVによる)。UV照射後、UV照射による一時的な固定品質を手動で評価した。ガラス基材を手動でずらすことができない場合、UV固定性を「良好」として記録し、ガラス基材を手動で簡単にずらすことができる場合を「不良」として記録した。
Claims (14)
- 前記組成物は、該組成物全体の10重量%〜90重量%、好ましくは20重量%〜80重量%、より好ましくは30重量%〜60重量%のマレイミド樹脂を含む、請求項1に記載の硬化性樹脂組成物。
- 前記熱フリーラジカル開始剤は、30-80℃の温度に10時間の半減期(10h T1/2)、より好ましくは40-70℃の温度に10h T1/2を有し、ここで、10h T1/2の温度は、熱フリーラジカル開始剤が、10時間後に本来存在する熱フリーラジカル開始剤の半分まで分解する温度として定義される、請求項1または2に記載の硬化性樹脂組成物。
- 前記組成物は、マレイミド樹脂の0.1重量%〜3重量%、好ましくは0.5重量%〜2重量%の熱フリーラジカル開始剤を含む、請求項1〜3のいずれかに記載の硬化性樹脂組成物。
- 前記固形エポキシ樹脂は、ポリスチレン標準を用いるゲルパーミエーションクロマトグラフィ(GPC)で測定して500〜3000g/molの数平均分子量を有する、請求項1〜4のいずれかに記載の硬化性樹脂組成物。
- 前記組成物はさらに液状エポキシ樹脂を含む、請求項1〜5のいずれかに記載の硬化性樹脂組成物。
- 前記潜伏性エポキシ硬化剤は、好ましくは50℃〜110℃、最も好ましくは60℃〜80℃の融点を有する、請求項1〜6のいずれかに記載の硬化性樹脂組成物。
- 前記組成物は、組成物全体の1重量%〜40重量%、好ましくは3重量%〜30重量%、最も好ましくは5重量%〜20重量%の潜伏性エポキシ硬化剤を含む、請求項1〜7のいずれかに記載の硬化性樹脂組成物。
- ビニルエーテル化合物または(メタ)アクリレート化合物を含む樹脂成分、並びに、有機または無機充填剤、チキソトロピー剤、シランカップリング剤、希釈剤、変性剤、着色剤、界面活性剤、防腐安定剤、可塑剤、潤滑油、消泡剤およびレベリング剤から選択される添加剤からなる群から選択される原料をさらに含む、請求項1〜8のいずれかに記載の硬化性樹脂組成物。
- 有機または無機充填剤、チキソトロピー剤、およびシランカップリング剤を好ましくは含む、請求項1〜9のいずれかに記載の硬化性樹脂組成物。
- 前記組成物は、レオメーターTA、AR2000 exを用いて本明細書に記載の方法に従い、25℃、15s-1で測定して、150〜450Pas、好ましくは25℃、15s-1で200〜400Pas、最も好ましくは25℃、15s-1で250〜350Pasの粘度を有する、請求項1〜10のいずれかに記載の硬化性樹脂組成物。
- 液晶をシーリングするための、請求項1〜11のいずれかに記載の硬化性樹脂組成物の使用。
- 以下のステップを含む、第1基材および第2基材の間の液晶層を有する液晶ディスプレイの製造方法:
1)請求項1〜11のいずれかに記載の硬化性樹脂組成物を第1基材の表面の周縁のシーリング領域に適用するステップ;
2)第1基材の表面の該シーリング領域で取り囲まれた中央領域に液晶を滴下するステップ;
3)第1基材上に第2基材を重ねるステップ;
4)UV硬化ステップ;および
5)熱硬化ステップ。 - 硬化は80℃〜130℃、好ましくは100℃〜120℃の温度で行われる、請求項13に記載の方法。
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KR102398715B1 (ko) * | 2016-05-13 | 2022-05-16 | 세키스이가가쿠 고교가부시키가이샤 | 액정 표시 소자용 시일제, 상하 도통 재료, 및 액정 표시 소자 |
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