JP2018163330A - 光硬化性組成物及びそれから形成された光硬化膜 - Google Patents
光硬化性組成物及びそれから形成された光硬化膜 Download PDFInfo
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- JP2018163330A JP2018163330A JP2018002985A JP2018002985A JP2018163330A JP 2018163330 A JP2018163330 A JP 2018163330A JP 2018002985 A JP2018002985 A JP 2018002985A JP 2018002985 A JP2018002985 A JP 2018002985A JP 2018163330 A JP2018163330 A JP 2018163330A
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- photocurable composition
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- polycyclic hydrocarbon
- compound
- acrylate compound
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- VTLHIRNKQSFSJS-UHFFFAOYSA-N [3-(3-sulfanylbutanoyloxy)-2,2-bis(3-sulfanylbutanoyloxymethyl)propyl] 3-sulfanylbutanoate Chemical compound CC(S)CC(=O)OCC(COC(=O)CC(C)S)(COC(=O)CC(C)S)COC(=O)CC(C)S VTLHIRNKQSFSJS-UHFFFAOYSA-N 0.000 description 1
- YAAUVJUJVBJRSQ-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2-[[3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propoxy]methyl]-2-(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS YAAUVJUJVBJRSQ-UHFFFAOYSA-N 0.000 description 1
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- JFZUABNDWZQLIJ-UHFFFAOYSA-N methyl 2-[(2-chloroacetyl)amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)CCl JFZUABNDWZQLIJ-UHFFFAOYSA-N 0.000 description 1
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
- C08F216/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
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- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
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- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- G—PHYSICS
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
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- Polymers & Plastics (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Devices For Indicating Variable Information By Combining Individual Elements (AREA)
- Materials For Photolithography (AREA)
- Electroluminescent Light Sources (AREA)
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Abstract
Description
アリルエーテル(allyl ether)化合物
本発明の実施形態に係る光硬化性組成物に含まれるアリルエーテル化合物は、実質的に組成物の粘度を下げる役割を果たすものであり、希釈剤として機能することができる。前記アリルエーテル化合物は、一般の感光性有機膜を形成するための組成物に含まれる溶剤を代替することができる。したがって、例示的な実施形態によると、前記光硬化性組成物は、実質的に無溶剤(solvent−freeまたはnon−solvent)タイプで製造及び活用することができる。
本発明の実施形態に係る光硬化性組成物は、反応性単量体または重合性単量体として、多環(multi−cyclic)炭化水素含有(メタ)アクリレート化合物を含むことができる。前記多環炭化水素含有(メタ)アクリレート化合物は、例えば、紫外線露光工程によりラジカル重合反応に参加し、所望の硬度又は硬化度を確保する主成分として含むことができる。
本発明の実施形態に係る光硬化性組成物は、カルボン酸含有単量体を含み、これにより、硬化膜のコーティング性及び密着性を向上することができる。一部の実施形態では、前記カルボン酸含有単量体は、カルボン酸含有(メタ)アクリレート単量体を含むことができる。
例示的な実施形態によると、光開始剤は、露光工程によりラジカルを発生し、前述したアリルエーテル化合物と多環炭化水素含有(メタ)アクリレート化合物との架橋反応または重合反応を誘導できるものであれば、特に制限されることなく用いることができる。例えば、前記光開始剤は、アセトフェノン系化合物、ベンゾフェノン系化合物、トリアジン系化合物、ビイミダゾール系化合物、チオキサントン系化合物、及びオキシムエステル系化合物からなる群より選択される少なくとも1種の化合物を用いることができ、好ましくは、オキシムエステル系化合物を用いることができる。
前記光硬化性組成物から形成された硬化膜の重合特性、硬化度および表面特性などを向上させるために、追加の製剤をさらに含むことができる。例えば、本発明の実施形態に係る光硬化性組成物の低粘度特性及び硬化特性を阻害しない範囲内でさらに添加剤を含んでもよい。
本発明は、前述した光硬化性組成物から製造される光硬化膜、及び該光硬化膜を備える画像表示装置を提供するものである。
下記表1、表2に示す成分と含量で実施例及び比較例に係る光硬化性組成物を製造した。
A−2:水酸基を含む3官能アリルエーテル化合物
A−3:水酸基を含む2官能アリルエーテル化合物
A−4:単官能アリルエーテル化合物(アリルエチルエーテル)
A’:3官能ビニルエーテル化合物
B−1:トリシクロデカンジメタノールジアクリレート(NK ESTER A−DCP:(株)新中村化学工業製)
B−2:イソボルニルアクリレート(NK ESTER A−IB:(株)新中村化学工業製)
B’−1:1,6−ヘキサンジオールジアクリレート(NK ESTER A−HD−N:(株)新中村化学工業製)
B’−2:単環炭化水素含有ジアクリレート
B’−3:ラウリルアクリレート(NK ESTER LA:(株)新中村化学工業製)
B’−4:シクロヘキシルアクリレート(Viscoat#155:(株)大阪有機化学製)
C:メタクリロイルオキシエチルスクシネート(NK ESTER A−SA:(株)新中村化学工業製)
D:オキシムエステル系化合物
E:ペンタエリスリトールテトラキス[3−メルカプトプロピオネート](PEMP:(株)SC化学製)
F:SH8400 Fluid(Dow−Corning−Toray製)
後述する評価方法により、表1及び表2の組成物またはそれから形成されたコーティング膜、光硬化膜の粘度、コーティング性、鉛筆硬度および酸素阻害を評価した。評価結果を下記の表3に示す。
実施例及び比較例に係る各組成物の粘度を粘度測定器(DV3T、Brookfield社製)を用いて測定した(測定条件:回転数20rpm/25℃)。
50mmX50mmに切断したシリコン(Si)ウエハ上に、実施例及び比較例に係る各組成物をスピンコートして3.0μm厚さになるようにコーティング膜を形成した。スピンコートを進行した後、5分間放置してコーティング膜の形状を観察し、下記のようにコーティング性を評価した。
○:コーティング膜が均一に広がり、表面が均一である(図4参照)
△:組成物が広がるが、表面不均一が肉眼で観察される(図5参照)
×:表面がウェッティングされず、液の乾きが発生し、コーティング膜が実質的に形成されていない(図6参照)
コーティング性を評価する際に形成されたコーティング膜に紫外線硬化を行い、光硬化膜を形成した。具体的には、UV硬化装置(Lichtzen社、Model No.LZ−UVC−F402−CMD)を用いて150mW/cm2の照度(UV−A領域320〜400nm基準)で120秒間紫外線を照射した。形成された光硬化膜に対し、鉛筆硬度測定器を用いて鉛筆硬度を測定した。具体的には、鉛筆(三菱社製)を光硬化膜に接触させた後、1kg荷重及び50mm/秒の速度で表面を引っ掻き、表面硬度を測定した。
実施例及び比較例の組成物をスピンコートして3.0μm厚さになるようにコーティング膜を形成した。スピンコートを進行して5分間放置後、UV硬化装置(Lichtzen社、Model No.LZ−UVC−F402−CMD)を用いて150mW/cm2の照度(UV−A領域320〜400nm基準)で60秒間紫外線を照射した(窒素置換を行わない。)。
×:表面硬化により、何ら跡がつかない(図7参照)
○:酸素阻害により、柔らかい表面に跡がつく(図8参照)
110:画素定義膜
120:有機発光素子
130:第1のエンキャプセレーション層
140,143:エンキャプセレーション層
145:第2のエンキャプセレーション層
Claims (16)
- 2官能以上のアリルエーテル化合物と、
1官能または2官能の多環炭化水素含有(メタ)アクリレート化合物と、
カルボン酸含有単量体と、
光開始剤とを含む、光硬化性組成物。 - 1〜3官能の多環炭化水素非含有(メタ)アクリレート化合物をさらに含む、請求項1に記載の光硬化性組成物。
- 1官能多環炭化水素含有(メタ)アクリレート化合物を用いる場合は、2官能以上の多環炭化水素非含有(メタ)アクリレート化合物を用いる、請求項4に記載の光硬化性組成物。
- 前記カルボン酸含有単量体は、単官能カルボン酸含有(メタ)アクリレート単量体を含む、請求項1に記載の光硬化性組成物。
- 組成物の全重量に対して、
前記2官能以上のアリルエーテル化合物10〜50重量%と、
前記多環炭化水素含有(メタ)アクリレート化合物40〜80重量%と、
前記カルボン酸含有単量体1〜5重量%と、
前記光開始剤1〜10重量%とを含む、請求項1に記載の光硬化性組成物。 - 多官能チオール化合物をさらに含む、請求項1に記載の光硬化性組成物。
- 無溶剤タイプで製造される、請求項1に記載の光硬化性組成物。
- ポリマーまたは樹脂成分を含まない、請求項1に記載の光硬化性組成物。
- 常温で20cp以下の粘度を有する、請求項1に記載の光硬化性組成物。
- 請求項1〜13のいずれか一項に記載の光硬化性組成物から形成された光硬化膜。
- 請求項1〜13のいずれか一項に記載の光硬化性組成物から形成された光硬化膜を含む、画像表示装置。
- ベース基板と、
該ベース基板上に配置された有機発光素子とをさらに含み、
前記光硬化膜は、前記有機発光素子のエンキャプセレーション層で提供される、請求項15に記載の画像表示装置。
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