JP2019526690A - シール材組成物 - Google Patents
シール材組成物 Download PDFInfo
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- JP2019526690A JP2019526690A JP2019529831A JP2019529831A JP2019526690A JP 2019526690 A JP2019526690 A JP 2019526690A JP 2019529831 A JP2019529831 A JP 2019529831A JP 2019529831 A JP2019529831 A JP 2019529831A JP 2019526690 A JP2019526690 A JP 2019526690A
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- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/223—Di-epoxy compounds together with monoepoxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/226—Mixtures of di-epoxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/38—Inkjet printing inks characterised by non-macromolecular additives other than solvents, pigments or dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/84—Passivation; Containers; Encapsulations
- H10K50/844—Encapsulations
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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Abstract
Description
本出願は、2016年12月9日付けの韓国特許出願第10−2016−0167797号に基づく優先権の利益を主張し、当該韓国特許出願の文献に開示されたすべての内容は、本明細書の一部として含まれる。
常温で硬化性化合物として脂環族エポキシ化合物(ダイセル社セロキサイド(Celloxide)2021P)、脂肪族エポキシ化合物1,4‐ブタンジオールジグリシジルエーテル(DE200、HAJIN CHEM TECH社)、単官能性硬化性化合物o‐クレシルグリシジルエーテル(HAJIN CHEM TECH社のLS692)およびオキセタン基含有硬化性化合物(東亜合成社のOXT‐212)を16:18:18:39.95(Celloxide2021P:DE200:LS692:OXT‐212)の重量比で混合容器に投入した。前記全体硬化性化合物100重量部に対して3.3重量部の光重合開始剤(TETRA CHEM社のUV693)、1.1重量部のフッ素系界面活性剤(DIC社のF447)、3.3重量部のカップリング剤(KBE‐402、SHIN‐ETSU)および0.05重量部の熱安定剤2,6‐ジ‐tert‐ブチル‐p‐クレゾール(シグマアルドリッチ社のBHT)をさらに混合容器に投入した。また、前記光重合開始剤100重量部に対して33.3重量部の光増減剤9,10‐2‐エチル‐9,10‐ジメトキシアントラセン(シグマアルドリッチ社)をさらに混合容器に投入した。
界面活性剤としてF447の代わりにフッ素系界面活性剤であるFC‐4430(3M社)を使用したことを除いて、実施例1と同じ方法でシール材組成物を製造した。
界面活性剤としてF447の代わりにシリコン系界面活性剤であるD8526(ダウコーニング社)を使用したことを除いて、実施例1と同じ方法でシール材組成物を製造した。
界面活性剤としてF447の代わりにシリコン系界面活性剤であるT2500(TEGO社)を使用したことを除いて、実施例1と同じ方法でシール材組成物を製造した。
界面活性剤としてF447の代わりにシリコン系界面活性剤であるB348(BYK社)を使用したことを除いて、実施例1と同じ方法でシール材組成物を製造した。
界面活性剤としてF447の代わりにシリコン系界面活性剤であるQ2‐5211(ダウコーニング社)を使用したことを除いて、実施例1と同じ方法でシール材組成物を製造した。
硬化性化合物として脂環族エポキシ化合物(ダイセル社セロキサイド(Celloxide)2021P)、脂肪族エポキシ化合物1,4‐ブタンジオールジグリシジルエーテル(DE200、HAJIN CHEM TECH社)、単官能性硬化性化合物o‐クレシルグリシジルエーテル(HAJIN CHEM TECH社)およびオキセタン基含有硬化性化合物(東亜合成社のOXT‐121)を15:4:24:46.95(Celloxide2021P:DE200:o‐クレシルグリシジルエーテル:OXT‐121)の重量比で混合容器に投入したことを除いて、実施例1と同じ方法でシール材組成物を製造した。
常温で硬化性化合物として脂環族エポキシ化合物(ダイセル社セロキサイド(Celloxide)8010)、脂肪族エポキシ化合物1,4‐ブタンジオールジグリシジルエーテル(DE200、HAJIN CHEM TECH社)、単官能性硬化性化合物2‐エチルヘキシルグリシジルエーテル(シグマアルドリッチ社)およびオキセタン基含有硬化性化合物(東亜合成社のOXT‐212)を17:10:7:58.45(Celloxide2021P:DE200:2‐エチルヘキシルグリシジルエーテル:OXT‐212)の重量比で混合容器に投入した。前記全体硬化性化合物100重量部に対して3.2重量部の光重合開始剤(I290)、1.1重量部のフッ素系界面活性剤(DIC社のF552)、3.2重量部のカップリング剤(KBM‐303、SHIN−ETSU)および0.05重量部の熱安定剤2,6‐ジ‐tert‐ブチル‐アルファ‐メトキシ‐パラ‐クレゾール(シグマアルドリッチ社)をさらに混合容器に投入した。また、前記光重合開始剤100重量部に対して16.7重量部の光増減剤9,10‐ジブトキシアントラセン(シグマアルドリッチ社のDBA)をさらに混合容器に投入した。
常温で硬化性化合物として脂環族エポキシ化合物(ダイセル社セロキサイド(Celloxide)2021P)、脂肪族エポキシ化合物1,4‐ブタンジオールジグリシジルエーテル(DE200、HAJIN CHEM TECH社)、単官能性硬化性化合物o‐クレシルグリシジルエーテル(HAJIN CHEM TECH社)およびオキセタン基含有硬化性化合物(東亜合成社のOXT‐212)を22:25:35:9.95(Celloxide2021P:DE200:o‐クレシルグリシジルエーテル:OXT‐212)の重量比で混合容器に投入した。前記全体硬化性化合物100重量部に対して3.3重量部の光重合開始剤(BASF社のIrgacure PAG 290、以下、I290)、1.1重量部のフッ素系界面活性剤(DIC社のF552)、3.3重量部のカップリング剤(KBM‐303、SHIN−ETSU)および0.05重量部の熱安定剤2,6‐ジ‐tert‐ブチル‐アルファ‐メトキシ‐パラ‐クレゾール(シグマアルドリッチ)をさらに混合容器に投入した。また、前記光重合開始剤100重量部に対して33.3重量部の光増減剤9,10‐ジブトキシアントラセン(シグマアルドリッチ社のDBA)をさらに混合容器に投入した。
実施例および比較例で製造したシール材組成物に対する表面エネルギーは、水滴型分析器(Drop Shape Analyzer、KRUSS社のDSA100製品)を使用して測定した。前記シール材組成物をSiNx基板に50μmの厚さと4cm2のコート面積(横:2cm、縦:2cm)で塗布して、封止膜の形成後(スピンコーター)、窒素の雰囲気下で常温で約10分間程度乾燥させた後、1000mW/cm2の強度で4000mJ/cm2の光量を通じてUV硬化させる。硬化後、前記膜に表面張力(surface tension)が公知されている脱イオン化水を落とし、その接触角を求める過程を5回繰り返して、得られた5個の接触角数値の平均値を求め、同一に、表面張力が公知されているジヨードメタンを落とし、その接触角を求める過程を5回繰り返して、得られた5個の接触角数値の平均値を求める。その後、求められた脱イオン化水とジヨードメタンに対する接触角の平均値を利用してOwens‐Wendt‐Rabel‐Kaelble方法により溶媒の表面張力に関する数値(Strom値)を代入して表面エネルギーを求めた。
SiNx基板に約50μmの厚さで実施例および比較例で製造したシール材組成物を塗布し、1000mW/cm2の強度で4000mJ/cm2の光量を通じてUV硬化させて封止膜を形成する。Park systems社のNX10を使用して表面粗さを測定した。
モード:断続(タッピング)、サンプル/ライン:256×256、走査速度:0.9〜1.0Hz
[AFMプローブ]
PPP‐CHR(Nanosensor)、物質:カンチレバーの検出器側の上のAlコーティング、共振周波数:204〜497kHz、力定数:10〜130N/m
SiNx基板に約50μmの厚さで実施例および比較例で製造したシール材組成物を塗布し、1000mW/cm2の強度で4000mJ/cm2の光量を通じてUV硬化させて封止膜を形成した。前記封止膜上に化学気相蒸着(CVD、chemical vapor deposition)を通じてシリコン窒化物(SiNx)を蒸着させて、厚さ2μmの無機物層を形成した。
31 基板
32 有機電子デバイス
33 有機層
34 無機層
35 保護膜
36 封止構造
37 封止フィルム
38 カバー基板
Claims (21)
- 封止膜の形態で硬化後の表面エネルギーが20mN/m〜30mN/mの範囲内であり、表面粗さが3.5nm以下であるシール材組成物。
- 少なくとも一つ以上の硬化性官能基を有する硬化性化合物を含む請求項1に記載のシール材組成物。
- 前記硬化性官能基は、オキセタン基、グリシジル基、イソシアネート基、ヒドロキシ基、カルボキシル基、アミド基、エポキシド基、スルフィド基、アセタル基およびラクトン基から選択される一つ以上である、請求項2に記載のシール材組成物。
- 前記硬化性化合物は、分子構造内に環形構造を有し、少なくとも二つ以上の硬化性官能基を有する硬化性化合物を含む、請求項2に記載のシール材組成物。
- 前記分子構造内に環形構造を有する化合物は、分子構造内の環構成原子が3個〜10個の範囲内である、請求項4に記載のシール材組成物。
- 前記硬化性化合物は単官能性硬化性化合物をさらに含む、請求項4に記載のシール材組成物。
- 前記単官能性硬化性化合物は、前記環形構造を有する硬化性化合物100重量部に対して65重量部〜165重量部の範囲内で含まれる、請求項6に記載のシール材組成物。
- 硬化性化合物は直鎖または分岐鎖の脂肪族硬化性化合物をさらに含む、請求項4に記載のシール材組成物。
- 前記脂肪族硬化性化合物は少なくとも二つ以上の硬化性官能基を有する、請求項8に記載のシール材組成物。
- 前記脂肪族硬化性化合物は、環形構造を有する硬化性化合物100重量部に対して20重量部以上、205重量部未満の範囲内で含まれる、請求項8に記載のシール材組成物。
- 前記硬化性化合物は、オキセタン基を有する硬化性化合物をさらに含む、請求項4に記載のシール材組成物。
- 前記オキセタン基を有する硬化性化合物は、少なくとも二つ以上のオキセタン基を有する、請求項11に記載のシール材組成物。
- 前記オキセタン基を有する硬化性化合物は、環形構造を有する硬化性化合物および単官能性硬化性化合物100重量部に対して50重量部〜150重量部で含まれる、請求項11に記載のシール材組成物。
- 界面活性剤をさらに含む請求項1に記載のシール材組成物。
- 前記界面活性剤は極性官能基を含む、請求項14に記載のシール材組成物。
- 前記界面活性剤はフッ素系化合物を含む、請求項14に記載のシール材組成物。
- 前記界面活性剤は、全体硬化性化合物100重量部に対して0.01重量部〜10重量部で含まれる、請求項14に記載のシール材組成物。
- 光開始剤をさらに含む請求項1に記載のシール材組成物。
- 基板と、前記基板上に形成された有機電子デバイスと、前記有機電子デバイスの前面をシールし、請求項1に記載のシール材組成物を含む有機層と、を含む有機電子装置。
- 上部に有機電子デバイスが形成された基板の上に、請求項1に記載のシール材組成物が前記有機電子デバイスの前面をシールするように有機層を形成する段階を含む有機電子装置の製造方法。
- 前記有機層を形成する段階は、インクジェット印刷、グラビアコート、スピンコート、スクリーン印刷またはリバースオフセットコートを含む、請求項20に記載の有機電子装置の製造方法。
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TWI675074B (zh) | 2019-10-21 |
KR102118375B1 (ko) | 2020-06-04 |
WO2018106085A1 (ko) | 2018-06-14 |
JP6719674B2 (ja) | 2020-07-08 |
US20200095455A1 (en) | 2020-03-26 |
TW201835262A (zh) | 2018-10-01 |
CN109690805B (zh) | 2021-04-16 |
CN109690805A (zh) | 2019-04-26 |
KR20180066879A (ko) | 2018-06-19 |
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