JP7214296B2 - 粘着剤組成物、表面保護フィルムおよび有機発光電子装置の製造方法 - Google Patents
粘着剤組成物、表面保護フィルムおよび有機発光電子装置の製造方法 Download PDFInfo
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- JP7214296B2 JP7214296B2 JP2021525211A JP2021525211A JP7214296B2 JP 7214296 B2 JP7214296 B2 JP 7214296B2 JP 2021525211 A JP2021525211 A JP 2021525211A JP 2021525211 A JP2021525211 A JP 2021525211A JP 7214296 B2 JP7214296 B2 JP 7214296B2
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Description
本出願は、2018年12月5日付で韓国特許庁に提出された韓国特許出願第10-2018-0155081号の出願日の利益を主張し、その内容のすべては本明細書に組み込まれる。
前記アクリル系重合体は、シリコーンを含む(メタ)アクリレート単量体;およびヒドロキシ基を含む(メタ)アクリレート単量体を単量体単位として含む粘着剤組成物を提供する。
前記アクリル系重合体は、シリコーンを含む(メタ)アクリレート単量体;およびヒドロキシ基を含む(メタ)アクリレート単量体を単量体単位として含む粘着剤層を提供する。
前記第2帯電防止層の前記基材フィルムが備えられた面の反対面に備えられた粘着剤層とを含む表面保護フィルムであって、
前記粘着剤層は、前述した粘着剤層である表面保護フィルムを提供する。
本明細書において、ある部分がある構成要素を「含む」とする時、これは、特に反対の記載がない限り、他の構成要素を除くのではなく、他の構成要素をさらに包含できることを意味する。
本明細書において、「p~q」は、「p以上q以下」の範囲を意味する。
本明細書において、(メタ)アクリレートは、アクリレートとメタクリレートをすべて含むものである。
前記粘着剤組成物は、ウレタン重合体;アクリル系重合体;および硬化剤を含む。
フェノールフタレイン指示薬:フェノールフタレイン原液0.5g、エタノール250g、および蒸留水250gを混合した溶液
水酸基価は下記の式で計算することができる。
水酸基価=28.05×(A-B)×F/(試料の量)
A:ブランク(blank)に必要な0.5N KOH(ml)
B:本テストに必要な0.5N KOH(ml)
F:1N HCL10mlにマグネチックバーとフェノールフタレイン指示薬10滴を入れた後、0.5N KOHで滴定する時のKOHの量(ml)
本明細書の一実施態様において、前記シリコーンを含む(メタ)アクリレート単量体に由来する単位は、下記化学式3で表されてもよい。
R1~R7は、互いに同一または異なり、それぞれ独立してアルキル基であり、
R8は、水素またはメチル基であり、
nは、0以上の整数であり、
Lは、直鎖または分枝鎖の2価の飽和炭化水素基;2価の単環状脂肪族飽和炭化水素基;2価の多環状飽和炭化水素基;2価の芳香族炭化水素基;芳香族炭化水素に環状飽和炭化水素が縮合された環の2価の基;-O-;-C(=O)-;-C(=O)-O-;または-S-であるか、前記基のうち2以上が連結された基である。
本明細書の一実施態様において、前記化学式3は、下記化学式3-1で表される。
R4、R8およびnの定義は、化学式3と同じであり、
mは、0~10の整数である。
本明細書の一実施態様において、前記イソシアネート系硬化剤は、ジイソシアネート化合物のオリゴマー、ポリマー、環状単量体、または通常の脂肪族または芳香族ジイソシアネート化合物から選択可能であり、相溶化されたジイソシアネート化合物のオリゴマーなどを入手して使用することができる。
本明細書の一実施態様において、前記アクリル系重合体は、前記ウレタン重合体100重量部に対して、10重量部以下で含まれる。
前記アクリル系重合体は、シリコーンを含む(メタ)アクリレート単量体;およびヒドロキシ基を含む(メタ)アクリレート単量体を単量体単位として含む粘着剤層を提供する。
前記第2帯電防止層の前記基材フィルムが備えられた面の反対面に備えられた粘着剤層とを含む表面保護フィルムであって、
前記粘着剤層は、ウレタン重合体;アクリル系重合体;および硬化剤の硬化物を含み、
前記アクリル系重合体は、シリコーンを含む(メタ)アクリレート単量体;およびヒドロキシ基を含む(メタ)アクリレート単量体を単量体単位として含む表面保護フィルムを提供する。
前記第2帯電防止層の前記基材フィルムが備えられた面の反対面に備えられた粘着剤層とを含む表面保護フィルムであって、
前記粘着剤層は、前述した粘着剤組成物の硬化物を含む表面保護フィルムを提供する。
前記保護層は、前記離型層が前記粘着剤層と向かい合うように備えられる。
前記第1~第4帯電防止層は、目的の効果を達成するために公知の方法で形成できる。例えば、前記第1~第4帯電防止層は、基材フィルムの両面および保護フィルムの両面にインラインコーティング方法によって形成できる。
前記離型層は、前記離型層材料を、例えば、保護層に塗布し乾燥して形成することができる。前記離型層材料のコーティングおよび乾燥方法としては、任意の適切なコーティング方法が適宜使用可能である。
前記粘着力(B)は、前記表面保護フィルムの粘着剤層をガラスに付着させ、60℃の温度および90%の相対湿度の条件で10日間保管した後、前記表面保護フィルムを前記ガラスから除去し、前記表面保護フィルムが除去された前記ガラス面に前記粘着剤(Ref.)を付着させ、前記粘着剤(Ref.)を前記ガラスから1.8m/minの剥離速度および180゜の剥離角度で剥離する時の剥離力であり、
前記粘着力(A)は、前記粘着剤(Ref.)をガラスから1.8m/minの剥離速度および180゜の剥離角度で剥離する時の剥離力である。
[式(1)]
残渣率(%)=(粘着力(B)/粘着力(A))×100
本明細書の一実施態様において、前記有機発光電子装置の製造方法は、前述した表面保護フィルムの粘着剤層を有機発光素子の封止層上に付着させるステップを含む。
<ウレタン重合体の製造>
窒素ガスで充填された3口フラスコに、3官能プレミノール(polyether polyol、S 4013F、ASAHI GLASS CO.LTD.,Mn=12,000g/mol)80重量部、2官能ポリオール(ポリプロピレングリコール、PPG-1000d、錦湖石油化学、Mn=1,000g/mol)5重量部、および3官能MPD/TMPT系ポリオール(MPD(3-methyl-1,5-pentanediol)とTMPT(trimethylol propane adipate)との混合物、Polyol F-3010、Kuraray社、Mn=3,000g/mol)15重量部とエチルアセテート(ethyl acetate)を投入し、触媒(DBTDL)下で15分高速撹拌した。次に、前記プレミノール、ポリオール、およびMPD/TMPT系ポリオール100重量部に対して、多官能性脂環族イソシアネート化合物(MHG-80B、ASAHI KASEI社)18重量部をゆっくり滴加しながら加熱して90±5℃で3時間維持し、イソシアネート(NCO)ピークが消滅するまで反応させて重量平均分子量が110,000g/molのウレタン重合体を製造した。
窒素ガスが還流し温度調節が容易となるように冷却装置を設けた1Lの反応器に、ブチルメタクリレート(BMA)90重量部、シリコーンを含むアクリレートFM-0721(CHISSO社、Mn=5,000g/mol)5重量部、および2-ヒドロキシブチルアクリレート(2-HBA)5重量部からなる単量体混合物を投入後、溶媒としてエチルアセテートを投入した。その後、酸素を除去するために窒素ガスを約1時間パージング(purging)した後、反応器の温度を62℃に維持した。混合物を均一にした後、反応開始剤としてアゾビスイソブチロニトリル(AIBN)400ppmおよび連鎖移動剤としてn-ドデシルメルカプタン(n-dodecylmercaptan、n-DDM)400ppmを投入し、混合物を反応させた。反応後にトルエンで希釈して重量平均分子量が34,000g/molのアクリル系重合体(D1)を製造した。
前記製造されたウレタン重合体、前記ウレタン重合体100重量部に対して、HDI Trimer系硬化剤(TKA-100、ASAHI KASEI社)15重量部、前記アクリル系重合体(D1)5重量部、触媒(DBTDL)0.005重量部、および硬化遅延剤(アセチルアセトン)3重量部を混合して、固形分の濃度が48wt%となるようにトルエン(Toluene)溶媒を入れて、ディスパー(disper)で撹拌して粘着剤組成物1を製造した。
BMA/FM-0721/2-HBAの重量比を90:5:5の代わりに85:5:10としたことを除けば、アクリル系重合体(D1)の製造方法と同様の方法で分子量36,000g/molのアクリル系重合体(D2)を製造した。
アクリル系重合体(D1)の代わりにアクリル系重合体(D2)を用いたことを除けば、粘着剤組成物1の製造方法と同様の方法で粘着剤組成物2を製造した。
BMA/FM-0721/2-HBAの重量比を90:5:5の代わりに86:9:5としたことを除けば、アクリル系重合体(D1)の製造方法と同様の方法で重量平均分子量29,000g/molのアクリル系重合体(D3)を製造した。
アクリル系重合体(D1)の代わりにアクリル系重合体(D3)を用いたことを除けば、粘着剤組成物1の製造方法と同様の方法で粘着剤組成物3を製造した。
BMA/FM-0721/2-HBAの重量比を90:5:5の代わりに81:9:10としたことを除けば、アクリル系重合体(D1)の製造方法と同様の方法で重量平均分子量26,000g/molのアクリル系重合体(D4)を製造した。
アクリル系重合体(D1)の代わりにアクリル系重合体(D4)を用いたことを除けば、粘着剤組成物1の製造方法と同様の方法で粘着剤組成物4を製造した。
BMA/FM-0721/2-HBAの重量比を90:5:5の代わりに80:5:15としたことを除けば、アクリル系重合体(D1)の製造方法と同様の方法で重量平均分子量30,000g/molのアクリル系重合体(D5)を製造した。
アクリル系重合体(D1)の代わりにアクリル系重合体(D5)を用いたことを除けば、粘着剤組成物1の製造方法と同様の方法で粘着剤組成物5を製造した。
アクリル系重合体(D1)を用いないことを除けば、粘着剤組成物1の製造方法と同様の方法で比較組成物1を製造した。
アクリル系重合体(D1)の代わりにイソプロピルミリステート(IPMS)をウレタン重合体100重量部に対して20重量部用いたことを除けば、粘着剤組成物1の製造方法と同様の方法で比較組成物2を製造した。
アクリル系重合体(D1)の代わりにイソプロピルミリステート(IPMS)をウレタン重合体100重量部に対して40重量部用いたことを除けば、粘着剤組成物1の製造方法と同様の方法で比較組成物3を製造した。
BMA/FM-0721/2-HBAの代わりにBMAを100重量部としたことを除けば、アクリル系重合体(D1)の製造方法と同様の方法で重量平均分子量32,000g/molのアクリル系重合体(E1)を製造した。
BMA/FM-0721/2-HBAの代わりにBMA/FM-0721の重量比を80:20としたことを除けば、アクリル系重合体(D1)の製造方法と同様の方法で重量平均分子量28,000g/molのアクリル系重合体(D6)を製造した。
アクリル系重合体(D1)の代わりにアクリル系重合体(D6)を用いたことを除けば、粘着剤組成物1の製造方法と同様の方法で比較組成物5を製造した。
基材層としては、基材フィルムの両面にそれぞれ50nmの帯電防止層がコーティングされた75μmの厚さのポリエチレンテレフタレート(PET)フィルム(H330、コーロン社)を用意した。保護層としては、50μmの厚さのポリエチレンテレフタレート(PET)フィルム(XD510P、TAK社)の両面に帯電防止層が形成され、1つの帯電防止層上に離型層がコーティングされたフィルム(12ASW、SKC社)を用意した。次に、前記基材層の一面に前記粘着剤組成物を75μmの厚さにコンマコーティングし熱風乾燥した後、前記基材層と前記離型層が向かい合うように粘着剤組成物上に離型コーティングされた保護層を貼り合わせて、40℃で5日間熟成した後、表面保護フィルムを製造した。
本出願の実施例および比較例における粘着剤層の物性は下記の方式で評価し、その結果を下記表2に示した。
実施例1~5および比較例1~4の表面保護フィルムを幅25mm、長さ150mmとなるように裁断した。次いで、2kgのローラを用いて表面保護フィルムの粘着剤層をガラスに付着させ、常温で約24時間保管する。次いで、装置(Texture Analyzer、英国のステーブルマイクロシステムズ社製)を用いて、前記粘着剤層が形成された基材フィルムをガラスから1.8m/minの剥離速度および180゜の剥離角度で剥離しながら低速剥離力を評価した。剥離力は2つの同じ試験片に対して測定した後に、その平均値を採用した。
ガラスから1.8m/minの剥離速度および180゜の剥離角度で剥離する時の剥離力が1,800±100gf/inである粘着剤(Ref.)を用意する。
粘着力(A)と(B)を下記の式に代入して、残渣率を得た。
残渣率(%)=(粘着力(B)/粘着力(A))×100
11B:第2帯電防止層
11C:第3帯電防止層
11D:第4帯電防止層
110:基材層
111:基材フィルム
123:離型層
124:粘着剤層
130:保護層
131:保護フィルム
140:被着材
510:有機発光素子
511:バックプレート
512:プラスチック基板
513:薄膜トランジスタ
514:有機発光ダイオード
515:封止層
Claims (14)
- ウレタン重合体;アクリル系重合体;および硬化剤を含み、
前記アクリル系重合体は、前記ウレタン重合体100重量部に対して、1重量部~10重量部含まれ、
前記アクリル系重合体は、炭素数8未満のアルキル(メタ)アクリレート単量体70重量%~98.9重量%;シリコーンを含む(メタ)アクリレート単量体0.1重量%~10重量%;およびヒドロキシ基を含む(メタ)アクリレート単量体1重量%~20重量%のランダム重合体である、粘着剤組成物。 - 前記シリコーンを含む(メタ)アクリレート単量体の数平均分子量は、500g/mol~10,000g/molである、請求項1または2に記載の粘着剤組成物。
- 前記アクリル系重合体の重量平均分子量は、10,000g/mol~60,000g/molである、請求項1~3のいずれか一項に記載の粘着剤組成物。
- 前記ウレタン重合体の重量平均分子量は、60,000g/mol~160,000g/molである、請求項1~4のいずれか一項に記載の粘着剤組成物。
- 前記硬化剤は、前記ウレタン重合体100重量部に対して、1重量部~25重量部含まれる、請求項1~5のいずれか一項に記載の粘着剤組成物。
- ウレタン重合体;アクリル系重合体;および硬化剤の硬化物を含む粘着剤層であって、
前記アクリル系重合体は、シリコーンを含む(メタ)アクリレート単量体;およびヒドロキシ基を含む(メタ)アクリレート単量体を単量体単位として含み、
前記アクリル系重合体は、前記ウレタン重合体100重量部に対して、1重量部~10重量部含まれ、
前記アクリル系重合体は、炭素数8未満のアルキル(メタ)アクリレート単量体70重量%~98.9重量%;シリコーンを含む(メタ)アクリレート単量体0.1重量%~10重量%;およびヒドロキシ基を含む(メタ)アクリレート単量体1重量%~20重量%のランダム重合体である、粘着剤層。 - 基材フィルムと、前記基材フィルムの両面にそれぞれ備えられた第1帯電防止層および第2帯電防止層とを含む基材層と、
前記第2帯電防止層の前記基材フィルムが備えられた面の反対面に備えられた粘着剤層とを含む表面保護フィルムであって、
前記粘着剤層は、請求項7に規定の粘着剤層である表面保護フィルム。 - 保護フィルムと、前記保護フィルムの両面にそれぞれ備えられた第3帯電防止層および第4帯電防止層と、前記第3帯電防止層の前記保護フィルムが備えられた面の反対面に備えられた離型層とを含む保護層をさらに含み、
前記保護層は、前記離型層が前記粘着剤層と向かい合うように備えられる、請求項8に記載の表面保護フィルム。 - 前記粘着剤層の前記基材層が備えられた面の反対面をガラスから1.8m/minの剥離速度および180゜の剥離角度で剥離する時の剥離力は、0.5gf/in以上10gf/in以下である、請求項8または9に記載の表面保護フィルム。
- 前記粘着剤層の前記基材層が備えられた面の反対面の残渣率は、80%以上である、請求項8~10のいずれか一項に記載の表面保護フィルム。
- 請求項8に規定の表面保護フィルムの粘着剤層を有機発光素子の封止層上に付着させるステップを含む有機発光電子装置の製造方法。
- 前記有機発光素子は、バックプレート、プラスチック基板、薄膜トランジスタ、有機発光ダイオード、および封止層を順に含む、請求項12に記載の有機発光電子装置の製造方法。
- 前記表面保護フィルムを前記封止層から剥離するステップと、前記封止層上にタッチスクリーンパネルおよびカバーウィンドウを積層するステップとをさらに含む、請求項12または13に記載の有機発光電子装置の製造方法。
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