JPWO2010001976A1 - 感光性組成物、隔壁、カラーフィルタ及び有機el素子 - Google Patents
感光性組成物、隔壁、カラーフィルタ及び有機el素子 Download PDFInfo
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- JPWO2010001976A1 JPWO2010001976A1 JP2010519117A JP2010519117A JPWO2010001976A1 JP WO2010001976 A1 JPWO2010001976 A1 JP WO2010001976A1 JP 2010519117 A JP2010519117 A JP 2010519117A JP 2010519117 A JP2010519117 A JP 2010519117A JP WO2010001976 A1 JPWO2010001976 A1 JP WO2010001976A1
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Images
Classifications
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- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
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- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
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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
- H10K50/86—Arrangements for improving contrast, e.g. preventing reflection of ambient light
- H10K50/865—Arrangements for improving contrast, e.g. preventing reflection of ambient light comprising light absorbing layers, e.g. light-blocking layers
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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
- H10K59/10—OLED displays
- H10K59/12—Active-matrix OLED [AMOLED] displays
- H10K59/122—Pixel-defining structures or layers, e.g. banks
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Abstract
Description
−CFXRf (1)
(式中、Xは、水素原子、フッ素原子又はトリフルオロメチル基であり、Rfは、エーテル性酸素原子を有していてもよい炭素数が1以上20以下のフルオロアルキル基、又はフッ素原子である。)
で表される基、又は、一般式
で表される基を有する側鎖と、エチレン性二重結合を有する側鎖とを有する重合体(A)、黒色の着色剤(B)、光重合開始剤(C)及び酸性基とエチレン性二重結合とを有する感光性樹脂(D)を含む感光性組成物であって、前記重合体(A)は、数平均分子量が2×104以上7×104以下であり、重量平均分子量が5×104以上25×104以下であることを特徴とする感光性組成物。なお、フルオロアルキル基とは、水素原子の少なくとも1つがフッ素原子に置換されたアルキル基を意味する。
[2]前記重合体(A)が、前記式(1)で表される基を有する側鎖と、エチレン性二重結合を有する側鎖とを有する重合体(A)であって、重合体(A)中のフッ素原子の含有量が5〜35質量%である上記[1]に記載の感光性組成物。
[3]前記重合体(A)が、前記式(2)で表される基を有する側鎖と、エチレン性二重結合を有する側鎖とを有する重合体(A)であって、重合体(A)中のケイ素原子の含有量が0.1〜25質量%である上記[1]に記載の感光性組成物。
[6]前記式(1)で表される基が、パーフルオロアルキル基である、上記[1]乃至[5]のいずれか1項に記載の感光性組成物。
[7]前記重合体(A)が、酸性基を有する側鎖をさらに有する、上記[1]乃至[6]のいずれか1項に記載の感光性組成物。
[8]エチレン性二重結合を2個以上有する架橋剤(E)をさらに含む上記[1]乃至[7]のいずれか一項に記載の感光性組成物。
−CFXRf (1)
(式中、Xは、水素原子、フッ素原子又はトリフルオロメチル基であり、Rfは、エーテル性酸素原子を有していてもよい炭素数が1〜20のフルオロアルキル基又はフッ素原子である。)
で表される基、又は、一般式
で表される基を有する側鎖と、エチレン性二重結合を有する側鎖とを有する重合体(A)、黒色の着色剤(B)、光重合開始剤(C)及び酸性基とエチレン性二重結合とを有する感光性樹脂(D)を含む。このとき、重合体(A)の数平均分子量は、2×104〜7×104であり、2.2×104〜6.5×104が好ましく、2.5×104〜6×104がより好ましい。また、重合体(A)の重量平均分子量は、5×104〜25×104であり、5.5×104〜22×104が好ましく、6×104〜20×104がより好ましい。なお、数平均分子量及び重量平均分子量は、ゲルパーミエーションクロマトグラフィー法により、ポリスチレンを標準物質として測定する。
CH2=CR4−COO−Y−CFXRf (3)
(式中、R4は、水素原子、フッ素原子、塩素原子、臭素原子、ヨウ素原子、トリフルオロメチル基、エーテル性酸素原子を有していてもよい炭素数が1〜20のフルオロアルキル基、シアノ基、炭素数1〜20のアルキル基、炭素数7〜20のアリール基で置換されたアルキル基、炭素数6〜20のアリール基、又は炭素数3〜20のシクロアルキル基、である。Yは、単結合又は炭素数が1〜6のフッ素原子を有さない2価の有機基である。Xは、水素原子、フッ素原子又はトリフルオロメチル基である。Rfは、エーテル性酸素原子を有していてもよい炭素数が1〜20のフルオロアルキル基、又はフッ素原子である。)
で表される化合物であることが好ましく、二種以上併用してもよい。なお、−CFXRfの好ましい態様は、上記基(1)に関して説明したのと同様である。また、Yとしては、−R5−、−R5−NR6−SO2−、−R5−NR6−CO−、−CH2CH(OH)−R7−(R5は、炭素数が1〜6のアルキレン基であり、R6は、水素原子又はメチル基であり、R7は、単結合又は炭素数が1〜4のアルキレン基である。)等が挙げられるが、入手の容易さから、炭素数が2〜4のアルキレン基が好ましい。
R4としては、水素原子、フッ素原子、塩素原子、メチル基、トリフルオロメチル基、フェニル基、ベンジル基等が挙げられ、水素原子、フッ素原子、塩素原子、メチル基、又はトリフルオロメチル基が好ましい。
で表される化合物であることが好ましく、二種以上併用してもよい。なお、R1、R2、R3及びnの好ましい態様は、上記基(2)に関して説明したのと同様である。また、Zは、炭素数が1〜6の2価の炭化水素基であることが好ましく、−CH2−、−CH2CH2−、−CH(CH3)−、−CH2CH2CH2−、−C(CH3)2−、−CH(CH2CH3)−、−CH2CH2CH2CH2−、−CH(CH2CH2CH3)−、−CH2(CH2)3CH2−、−CH(CH2CH(CH3)2)−等が挙げられる。
(1)水酸基に対し、エチレン性二重結合を有する酸無水物、
(2)水酸基に対し、イソシアネート基とエチレン性二重結合を有する化合物、
(3)水酸基に対し、塩化アシル基とエチレン性二重結合を有する化合物、
(4)酸無水物に対し、水酸基とエチレン性二重結合を有する化合物、
(5)カルボキシ基に対し、エポキシ基とエチレン性二重結合を有する化合物、
(6)エポキシ基に対し、カルボキシ基とエチレン性二重結合を有する化合物。
1−[4−(フェニルチオ)−,2−(O−ベンゾイルオキシム)]、エタノン 1−[9−エチル−6−(2−メチルベンゾイル)−9H−カルバゾイル−3−イル]−1−(O−アセチルオキシム)等のオキシムエステル類等が挙げられ、二種以上併用してもよい。中でも、一般式
で表される化合物が好ましい。
これにより、隔壁と基板との密着性を向上させることができる。
まず、本発明の感光性組成物の希釈液を基板に塗布する。基板としては、特に限定されず、各種ガラス板;SiC基板、シリコン等の無機基板;ITO等の無機酸化物基板;ポリエステル(ポリエチレンテレフタレート等)、ポリオレフィン(ポリエチレン、ポリプロピレン等)、ポリカーボネート、ポリメチルメタクリレート、ポリスルホン、ポリイミド、ポリ(メタ)アクリル樹脂等の熱可塑性樹脂シート;エポキシ樹脂、不飽和ポリエステル等の熱硬化性樹脂の硬化シート等が挙げられるが、耐熱性を考慮すると、ガラス板、ポリイミド等の耐熱性樹脂が好ましい。また、基板の隔壁が形成されていない側の面からの露光が可能であることから、基板は、透明であることが好ましい。さらに、基板は、ガラス基板等の透明基板上に、有機膜又はTFT、ITO、SiO2等の無機酸化物膜が形成された基板又はパターニングされた基板、シリコンナイトライドやポリイミドなどの絶縁膜を形成させた基板、これらの基板が積層されている積層基板であってもよい。
次に、基板に形成された塗膜を乾燥する。これにより、溶媒が揮発するため、粘着性の無い感光性組成物の塗膜が得られる。乾燥方法としては、特に限定されず、真空乾燥、加熱乾燥が挙げられるが、塗膜の外観のムラを発生させず、効率よく乾燥させるために、真空乾燥と加熱乾燥を併用することが好ましい。乾燥条件は、感光性組成物に含まれる成分の種類、組成等により異なるが、真空乾燥は、10〜500Pa(絶対圧)で10〜300秒間であることが好ましく、加熱乾燥は、50〜120℃で10〜2000秒間であることが好ましい。
次に、所定パターンのマスクを介して、塗膜を露光する。露光時に照射される光としては、特に限定されず、可視光、紫外線、遠紫外線、KrFエキシマレーザー、ArFエキシマレーザー、F2エキシマレーザー、Kr2エキシマレーザー、KrArエキシマレーザー、Ar2エキシマレーザー等のエキシマレーザー、X線、電子線等が挙げられるが、波長が100〜600nmの光が好ましく、波長が300〜500nmの光がより好ましく、i線(365nm)、h線(405nm)、g線(436nm)が特に好ましい。なお、光源としては、公知の超高圧水銀灯等を用いることができる。
次に、現像液を用いて、塗膜の未露光部を除去し、現像する。現像液としては、特に限定されないが、無機アルカリ類、アミン類、アルコールアミン類、第4級アンモニウム塩等のアルカリの水溶液が挙げられる。現像時間、即ち、現像液に接触させる時間は、5〜180秒間であることが好ましい。現像方法としては、特に限定されないが、液盛り法、ディッピング法、シャワー法等が挙げられる。
次に、現像された隔壁に対してポスト露光を行ってもよい。このとき、隔壁が形成されている側の面及び隔壁が形成されていない側の面のいずれから露光してもよいし、両面から露光してもよい。露光時に照射される光は、紫外線であることが好ましい。
現像後(ポスト露光を行う際は、ポスト露光後)に、隔壁を加熱することが好ましい。加熱条件は、150〜250℃で5〜90分間であることが好ましく、加熱温度は、180℃以上がより好ましい。加熱温度が低すぎると、耐薬品性が不十分となることがあり、隔壁にインクを塗布した場合に、隔壁が膨潤したり、インクが滲んだりすることがある。一方、加熱温度が高すぎると、隔壁が熱分解することがある。
X−8201:ジメチルシリコーン鎖含有メタクリレートX−24−8201(信越化学工業社製)
C6FMA:CH2=C(CH3)COOCH2CH2(CF2)6F
MAA:メタクリル酸
2−HEMA:2−ヒドロキシエチルメタクリレート
IBMA:イソボルニルメタクリレート
V−70:V−70(和光純薬社製、2,2'−アゾビス(4−メトキシ−2,4−ジメチルバレロニトリル))
2−ME:2−メルカプトエタノール
AOI:カレンズAOI(昭和電工社製、2−アクリロイルオキシエチルイソシアネート)
BEI:カレンズBEI(昭和電工社製、1,1−ビス(アクリロイルオキシメチル)エチルイソシアネート)
DBTDL:ジブチル錫ジラウレート
BHT:2,6−ジ−t−ブチル−p−クレゾール
MEK:2−ブタノン
OXE02:OXE02(チバスペシャルティケミカルズ社製、エタノン 1−[9−エチル−6−(2−メチルベンゾイル)−9H−カルバゾイル−3−イル]−1−(O−アセチルオキシム)(一般式(5)において、R1及びR2がメチル基、R3がエチル基、R4、R6及びR7が水素原子、R5が2−メチルベンゾイル基である化合物)
EX1010:EX−1010(ナガセケムテックス社製、一般式(7)で表されるエポキシ樹脂にエチレン性二重結合と酸性基とを導入した樹脂の溶液;固形分70%、重量平均分子量3020)
ZCR1569:ZCR−1569(日本化薬社製、一般式(6)で表されるビフェニル骨格を有するエポキシ樹脂にエチレン性二重結合と酸性基とを導入した樹脂の溶液;固形分70%、重量平均分子量4710)
ZCR1629:ZCR−1629(日本化薬社製、一般式(6)で表されるビフェニル骨格を有するエポキシ樹脂にエチレン性二重結合と酸性基とを導入した樹脂の溶液;固形分70%、重量平均分子量14500)
DPHA:KAYARAD DPHA(日本化薬社製、ジペンタエリスリトールペンタアクリレートとジペンタエリスリトールヘキサアクリレートの混合物)
A9300:NKエステル A−9300(新中村化学工業社製、エトキシ化イソシアヌル酸トリアクリレート)
PGMEA:プロピレングリコール1−モノメチルエーテル2−アセテート
CB:カーボンブラック分散液(平均二次粒径120nm、分散媒PGMEA、カーボンブラック20%、アミン価が18mgKOH/gのポリウレタン系高分子分散剤5%) シリカ:シリカ分散液(平均粒径20nm、分散媒PGMEA、固形分30%、シリカは負に帯電している。)
[重合体(A−1)の合成]
撹拌機を備えた内容積1Lのオートクレーブに、MEK(420.0g)、X−174DX(5.4g)、MAA(18.0g)、2−HEMA(99.0g)、IBMA(57.6g)及び重合開始剤V−70(2.0g)を仕込み、窒素雰囲気下で撹拌しながら、30℃で24時間重合させ、粗共重合体を合成した。得られた粗共重合体の溶液にヘプタンを加えて再沈精製した後、真空乾燥し、共重合体1(149.2g)を得た。共重合体1は、数平均分子量が17100、重量平均分子量が50500であった。
重合体(A−1)の合成において、原料の配合を表1のように変更した他は同様の反応により、共重合体2〜9の作製を経て、重合体(A−2)〜(A−5)、(R−1)、(R−2)を得た。得られた重合体の収量、数平均分子量(Mn)、重量平均分子量(Mw)、ケイ素原子(Si)の含有量、フッ素原子(F)の含有量、エチレン性二重結合(C=C)の含有量、酸価を表1に示す。
重合体(A−1)(0.22部)、黒色着色剤(B)の分散液としてのCB(58.9部)、光重合開始剤(C)としてのOXE02(2.1部)、感光性樹脂(D)の分散液としてのEX1010(13.1部)、架橋剤(E)としてのDPHA(3.9部)及び溶媒としてのPGMEA(21.7部)を混合して、感光性組成物の希釈液を得た。感光性組成物の希釈液の全固形分中の重合体(A−1)の含有量は、0.74%であった。
各成分の配合を表2に示すように変更した以外は、実施例1と同様にして、隔壁が形成されたガラス基板(1)、及び、感光性組成物の塗膜の硬化物が形成されたガラス基板(2)を得た。
実施例1〜6及び比較例1、2のガラス基板(1)及び(2)を用いて、現像性、撥水撥油性、開口部内のインクの濡れ拡がり性を以下に示す方法で評価した。評価結果を表2に示す。
ガラス基板(1)において、隔壁が完全に現像できたものを○、現像されない部分があったものを×として、判定した。
ガラス基板(2)の塗膜硬化物の表面の水の接触角を測定することにより、撥水性を評価した。接触角とは、固体と液体が接触する点における液体表面に対する接線と固体表面がなす角であり、液体を含む側の角度で定義する。このため、接触角が大きい程、塗膜硬化物の撥水性が優れることを意味する。
ガラス基板(2)の塗膜硬化物の表面のPGMEAの接触角を測定することにより、撥油性を評価した。接触角の定義は、撥水性と同様であり、接触角が大きい程、塗膜硬化物の撥油性が優れることを意味する。
液状エポキシME−562(日本ペルノックス社製)(6.25g)、硬化剤HV−562(日本ペルノックス社製)(6.25g)、アジピン酸ジエチル(12.5g)及びマロン酸ジエチル(25.0g)を、スターラーを用いて、1時間攪拌混合し、インクを調製した。
なお、2008年7月3日に出願された日本特許出願2008−174974号の明細書、特許請求の範囲、図面及び要約書の全内容をここに引用し、本発明の明細書の開示として、取り入れるものである。
Claims (11)
- 一般式
−CFXRf (1)
(式中、Xは、水素原子、フッ素原子又はトリフルオロメチル基であり、Rfは、エーテル性酸素原子を有していてもよい炭素数が1以上20以下のフルオロアルキル基又はフッ素原子である。)
で表される基、又は、一般式
で表される基を有する側鎖と、エチレン性二重結合を有する側鎖とを有する重合体(A)、黒色の着色剤(B)、光重合開始剤(C)及び酸性基とエチレン性二重結合とを有する感光性樹脂(D)を含む感光性組成物であって、
前記重合体(A)は、数平均分子量が2×104以上7×104以下であり、重量平均分子量が5×104以上25×104以下であることを特徴とする感光性組成物。 - 前記重合体(A)が、前記式(1)で表される基を有する側鎖と、エチレン性二重結合を有する側鎖とを有する重合体(A)であって、重合体(A)中のフッ素原子の含有量が5〜35質量%である請求項1に記載の感光性組成物。
- 前記重合体(A)が、前記式(2)で表される基を有する側鎖と、エチレン性二重結合を有する側鎖とを有する重合体(A)であって、重合体(A)中のケイ素原子の含有量が0.1〜25質量%である請求項1に記載の感光性組成物。
- 前記感光性樹脂(D)は、重量平均分子量が1.5×103以上20×103以下である請求項1乃至3のいずれか1項に記載の感光性組成物。
- 前記重合体(A)が、エチレン性二重結合を1.0〜5.0mmol/g含有する、請求項1乃至4のいずれか1項に記載の感光性組成物。
- 前記式(1)で表される基が、パーフルオロアルキル基である、請求項1乃至5のいずれか1項に記載の感光性組成物。
- 前記重合体(A)が、酸性基を有する側鎖をさらに有する、請求項1乃至6のいずれか1項に記載の感光性組成物。
- エチレン性二重結合を2個以上有する架橋剤(E)をさらに含む請求項1乃至7のいずれか1項に記載の感光性組成物。
- 請求項1乃至8のいずれか1項に記載の感光性組成物を硬化することにより形成されていることを特徴とする隔壁。
- 基板上に複数の画素が形成されているカラーフィルタであって、
該複数の画素は、請求項9に記載の隔壁で隔てられていることを特徴とするカラーフィルタ。 - 基板上に複数の画素が形成されている有機EL素子であって、
該複数の画素は、請求項9に記載の隔壁で隔てられていることを特徴とする有機EL素子。
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CN104684994B (zh) | 2012-09-24 | 2016-08-24 | 旭硝子株式会社 | 拒墨性组合物、负型感光性树脂组合物、固化膜、分隔壁以及光学元件 |
JP6509493B2 (ja) * | 2014-03-17 | 2019-05-08 | 株式会社日本触媒 | 硬化性樹脂組成物及びその用途 |
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