JP5900203B2 - 着色組成物、カラーフィルタ及び表示素子 - Google Patents
着色組成物、カラーフィルタ及び表示素子 Download PDFInfo
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- JP5900203B2 JP5900203B2 JP2012154399A JP2012154399A JP5900203B2 JP 5900203 B2 JP5900203 B2 JP 5900203B2 JP 2012154399 A JP2012154399 A JP 2012154399A JP 2012154399 A JP2012154399 A JP 2012154399A JP 5900203 B2 JP5900203 B2 JP 5900203B2
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Images
Classifications
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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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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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
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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
- G02F1/1303—Apparatus specially adapted to the manufacture of LCDs
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- 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
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
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- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Liquid Crystal (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
着色組成物
以下、本発明の着色組成物の構成成分について説明する。
本発明において(A)着色剤は、(a1)キノフタロン系黄色顔料及び黄色染料よりなる群から選ばれる少なくとも1種と、(a2)緑色着色剤とを含有するものである。キノフタロン系黄色顔料としては、特に限定されるものではないが、C.I.ピグメントイエロー138が好ましい。また、黄色染料としては、特に限定されるものではないが、例えば、バルビツール酸アゾ系染料、ピリドンアゾ系染料、ピラゾロンアゾ系染料、キノフタロン系染料、シアニン系染料等を挙げることができる。より具体的には、特開2010−168531号公報に開示されている黄色染料や、C.I.ピグメントイエロー138のスルホン化誘導体等を挙げることができる。本発明においては、これらの染料の中でも、所望の効果がより顕著に得られる点でキノフタロン系染料が好ましい。
本発明の着色組成物におけるバインダー樹脂としては、特に限定されるものではないが、カルボキシル基、フェノール性水酸基等の酸性官能基を有する樹脂であることが好ましい。中でも、カルボキシル基を有する重合体(以下、「カルボキシル基含有重合体」という。)が好ましく、例えば、1個以上のカルボキシル基を有するエチレン性不飽和単量体(以下、「不飽和単量体(b1)」という。)と、他の共重合可能なエチレン性不飽和単量体(以下、「不飽和単量体(b2)」という。)との共重合体を挙げることができる。
N−フェニルマレイミド、N−シクロヘキシルマレイミドの如きN−位置換マレイミド;
スチレン、α−メチルスチレン、p−ヒドロキシスチレン、p−ヒドロキシ−α−メチルスチレン、p−ビニルベンジルグリシジルエーテル、アセナフチレンの如き芳香族ビニル化合物;
ポリスチレン、ポリメチル(メタ)アクリレート、ポリ−n−ブチル(メタ)アクリレート、ポリシロキサンの如き重合体分子鎖の末端にモノ(メタ)アクリロイル基を有するマクロモノマー等を挙げることができる。
本発明において(C)架橋剤は、特定架橋剤、即ち2個以上の重合性不飽和基を有し、且つ2個以上の重合性不飽和基のうち少なくとも1個が上記式(1)で表される基である化合物を含有することを特徴とする。架橋剤として特定架橋剤を使用することにより、高温の加熱工程を経ても、500〜600nmにおける透過率の低下度が小さい硬化膜を得ることができ、その結果、輝度の高い緑色画素を形成することが可能となる。
本発明の着色組成物には、(D)光重合開始剤を含有せしめることができる。これにより、着色組成物に感放射線性を付与することができる。本発明に用いる(D)光重合開始剤は、可視光線、紫外線、遠紫外線、電子線、X線等の放射線の露光により、上記(C)架橋剤の重合を開始しうる活性種を発生する化合物である。
本発明の着色組成物は、上記(A)〜(C)成分、及び任意的に加えられる他の成分を含有するものであるが、通常、溶媒を配合して液状組成物として調製される。
エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノ−n−プロピルエーテル、エチレングリコールモノ−n−ブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノ−n−プロピルエーテル、ジエチレングリコールモノ−n−ブチルエーテル、トリエチレングリコールモノメチルエーテル、トリエチレングリコールモノエチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノ−n−プロピルエーテル、プロピレングリコールモノ−n−ブチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノ−n−プロピルエーテル、ジプロピレングリコールモノ−n−ブチルエーテル、トリプロピレングリコールモノメチルエーテル、トリプロピレングリコールモノエチルエーテル等の(ポリ)アルキレングリコールモノアルキルエーテル類;
メタノール、エタノール、プロパノール、ブタノール、イソプロパノール、イソブタノール、t−ブタノール、オクタノール、2−エチルヘキサノール、シクロヘキサノール等の(シクロ)アルキルアルコール類;
ジアセトンアルコール等のケトアルコール類;
ジエチレングリコールジメチルエーテル、ジエチレングリコールメチルエチルエーテル、ジエチレングリコールジエチルエーテル、テトラヒドロフラン等の他のエーテル類;
メチルエチルケトン、シクロヘキサノン、2−ヘプタノン、3−ヘプタノン等のケトン類;
3−メトキシプロピオン酸メチル、3−メトキシプロピオン酸エチル、3−エトキシプロピオン酸メチル、3−エトキシプロピオン酸エチル、エトキシ酢酸エチル、3−メチル−3−メトキシブチルプロピオネート等のアルコキシカルボン酸エステル類;
酢酸エチル、酢酸n−プロピル、酢酸i−プロピル、酢酸n−ブチル、酢酸i−ブチル、ぎ酸n−アミル、酢酸i−アミル、プロピオン酸n−ブチル、酪酸エチル、酪酸n−プロピル、酪酸i−プロピル、酪酸n−ブチル、ピルビン酸メチル、ピルビン酸エチル、ピルビン酸n−プロピル、アセト酢酸メチル、アセト酢酸エチル、2−オキソブタン酸エチル等の他のエステル類;
トルエン、キシレン等の芳香族炭化水素類;
N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N−メチルピロリドン等のアミド又はラクタム類
等を挙げることができる。
本発明の着色組成物は、必要に応じて、種々の添加剤を含有することもできる。
本発明のカラーフィルタは、本発明の着色組成物を用いて形成された画素を備えるものである。
また、上記アルカリ現像液としては、例えば、炭酸ナトリウム、水酸化ナトリウム、水酸化カリウム、テトラメチルアンモニウムハイドロオキサイド、コリン、1,8−ジアザビシクロ−[5.4.0]−7−ウンデセン、1,5−ジアザビシクロ−[4.3.0]−5−ノネン等の水溶液が好ましい。
本発明の表示素子は、本発明のカラーフィルタを具備するものである。表示素子としては、カラー液晶表示素子、有機EL表示素子、電子ペーパー等を挙げることができる。
合成例1
冷却管と攪拌機を備えたフラスコに、プロピレングリコールモノメチルエーテルアセテート100質量部を仕込んで窒素置換した。80℃に加熱して、同温度で、プロピレングリコールモノメチルエーテルアセテート50質量部、メタクリル酸20質量部、スチレン10質量部、ベンジルメタクリレート5質量部、2−ヒドロキシエチルメタクリレート15質量部、2−エチルヘキシルメタクリレート23質量部、N−フェニルマレイミド12質量部、こはく酸モノ(2−アクリロイロキシエチル)15質量部及び2,2'−アゾビス(2,4−ジメチルバレロニトリル)6質量部の混合溶液を1時間かけて滴下し、この温度を保持して2時間重合した。その後、反応溶液の温度を90℃に昇温させ、さらに1時間重合することにより、バインダー樹脂溶液を得た。得られたバインダー樹脂は、Mw=11900、Mn=5700、固形分濃度=40質量%であった。このバインダー樹脂を「バインダー樹脂(B−1)」とする。
冷却管と攪拌機を備えたフラスコに、プロピレングリコールモノメチルエーテルアセテート100質量部を仕込んで窒素置換した。80℃に加熱して、同温度で、プロピレングリコールモノメチルエーテルアセテート50質量部、メタクリル酸20質量部、スチレン10質量部、ベンジルメタクリレート5質量部、2−ヒドロキシエチルメタクリレート15質量部、2−エチルヘキシルメタクリレート38質量部、N−フェニルマレイミド12質量部及び2,2'−アゾビス(2,4−ジメチルバレロニトリル)6質量部の混合溶液を1時間かけて滴下し、この温度を保持して2時間重合した。その後、反応溶液の温度を100℃に昇温させ、さらに1時間重合することにより、バインダー樹脂溶液を得た。得られたバインダー樹脂は、Mw=11,000、Mn=6,000、固形分濃度=40質量%であった。このバインダー樹脂を「バインダー樹脂(B−2)」とする。
調製例1
(A)着色剤としてC.I.ピグメントグリーン58/C.I.ピグメントイエロー150(アゾ系黄色顔料)/C.I.ピグメントイエロー138=52/36/12(質量比)混合物15質量部、分散剤としてBYK−LPN21116(ビックケミー(BYK)社製)を11質量部(固形分濃度=40質量%)、バインダー樹脂(B−1)溶液を14質量部、溶媒としてプロピレングリコールモノメチルエーテルアセテート60質量部を用いて、ビーズミルにより混合・分散して、顔料分散液(A−1)を調製した。
(A)着色剤としてC.I.ピグメントグリーン58/C.I.ピグメントイエロー138/C.I.ピグメントイエロー138のスルホン化誘導体=46/52/2(質量比)混合物15質量部、分散剤としてBYK−LPN21116(ビックケミー(BYK)社製)を11質量部(固形分濃度=40質量%)、バインダー樹脂(B−1)溶液を14質量部、溶媒としてプロピレングリコールモノメチルエーテルアセテート60質量部を用いて、ビーズミルにより混合・分散して、顔料分散液(A−2)を調製した。
(A)着色剤としてC.I.ピグメントグリーン58/C.I.ピグメントイエロー150(アゾ系黄色顔料)=55/45(質量比)混合物15質量部、分散剤としてBYK−LPN21116(ビックケミー(BYK)社製)を11質量部(固形分濃度=40質量%)、バインダー樹脂(B−1)溶液を14質量部、溶媒としてプロピレングリコールモノメチルエーテルアセテート60質量部を用いて、ビーズミルにより混合・分散して、顔料分散液(A−3)を調製した。
実施例1
顔料分散液(A−1)210質量部、(B)バインダー樹脂としてバインダー樹脂(B−2)溶液50質量部、(C)架橋剤として日本化薬株式会社製KAYARAD DPCA−60(上記式(1)〜(3)においてm=1、式(1)で表される基の数=6、R1及びR3が全て水素原子、R2がペンタン−1,5−ジイル基である化合物)25質量部、(D)光重合開始剤として2−ベンジル−2−ジメチルアミノ−1−(4−モルフォリノフェニル)−ブタン−1−オン20質量部(BASF社製、商品名イルガキュア369)、フッ素系界面活性剤としてDIC株式会社製メガファックF−554を0.60質量部、溶剤として3−メトキシブチルアセテートを混合して、固形分濃度20質量%の液状着色組成物(S−1)を調製した。
実施例1において、表1に示す顔料分散液、架橋剤等に変更した以外は、実施例1と同様にして液状着色組成物(S−2)〜(S−12)を調製した。
C−1:上記式(1)〜(3)においてm=1、式(1)で表される基の数=6、R1及びR3が全て水素原子、R2がペンタン−1,5−ジイル基である化合物(商品名KAYARAD DPCA−60、日本化薬社製)
C−2:上記式(1)〜(3)においてm=2、式(1)で表される基の数=6、R1及びR3が全て水素原子、R2がペンタン−1,5−ジイル基である化合物(商品名KAYARAD DPCA−120、日本化薬社製)
C−3: ジペンタエリスリトールヘキサアクリレートとジペンタエリスリトールペンタアクリレートの混合物(商品名KAYARAD MAX−3510、日本化薬社製)
C−4: ペンタエリスリトールトリアクリレートとペンタエリスリトールテトラアクリレートの混合物(商品名アロニックスM−450、東亞合成社製)
C−5:エチレンオキサイド変性ジペンタエリスリトールヘキサアクリレート(商品名KAYARAD DPEA−12、日本化薬社製)
C−6:ジペンタエリスリトールペンタアクリレートとこはく酸とのモノエステル化物、ジペンタエリスリトールヘキサアクリレート並びにジペンタエリスリトールペンタアクリレートの混合物(商品名アロニックスTO−1382、東亞合成社製)
C−7:イソシアヌル酸エチレンオキサイド変性ジアクリレートとトリアクリレートの混合物(商品名アロニックスM−315、東亞合成社製)
顔料分散液(A−1)よりキノフタロン系黄色顔料と黄色染料の含有割合が多い顔料分散液(A−2)を使用した場合、かかる傾向は更に顕著になる。即ち、特定架橋剤を適用していない比較例6では、ポストベーク前後で透過率(%)が3ポイント以上低下しているのに対し、特定架橋剤を適用した実施例3〜4では、0.9〜1.0ポイントしか低下していない。なお、参考例1〜2から分かるように、黄色着色剤としてキノフタロン系黄色顔料も黄色染料も使用しない場合は、特定架橋剤を適用しても適用しなくても、ポストベーク前の透過率(%)及びY値、並びにポストベーク前後での透過率(%)及びY値の低下度合とも同程度であり差は認められない。即ち、特定架橋剤を適用することにより透過率(%)及びY値の低下を抑制できるという効果は、黄色着色剤としてキノフタロン系黄色顔料か黄色染料を使用する場合に特有のものである。
Claims (9)
- 前記(C)架橋剤として、多価アルコール、(メタ)アクリル酸及びラクトン類を反応させて得られる多官能(メタ)アクリレートを含有する、請求項1に記載の着色組成物。
- 前記(a1)黄色染料及びキノフタロン系黄色顔料よりなる群から選ばれる少なくとも1種として、キノフタロン系黄色顔料、又はキノフタロン系黄色顔料と黄色染料との混合物を含有する、請求項3に記載の着色組成物。
- 前記キノフタロン系黄色顔料として、C.I.ピグメントイエロー138を含有する、請求項4に記載の着色組成物。
- 前記2個以上の重合性不飽和基を有し、且つ2個以上の重合性不飽和基のうち少なくとも1個が前記式(1)で表される基である化合物の含有量が、前記(B)バインダー樹脂100質量部に対して10〜98質量部である、請求項1〜5のいずれか1項に記載の着色組成物。
- 前記(a2)緑色着色剤として、ハロゲン化亜鉛フタロシアニンを含有する、請求項1〜6のいずれか1項に記載の着色組成物。
- 請求項1〜7のいずれか1項に記載の着色組成物を用いて形成された画素を備えてなるカラーフィルタ。
- 請求項8に記載のカラーフィルタを具備する表示素子。
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CN103499911A (zh) * | 2008-03-14 | 2014-01-08 | Jsr株式会社 | 用于形成着色层的放射线敏感性组合物、滤色器和彩色液晶显示元件 |
TWI456345B (zh) * | 2008-06-03 | 2014-10-11 | Sumitomo Chemical Co | 著色硬化性組成物 |
JP5663878B2 (ja) * | 2009-02-18 | 2015-02-04 | Jsr株式会社 | 着色感放射線性組成物、カラーフィルタおよびカラー液晶表示素子 |
JP5515714B2 (ja) * | 2009-12-16 | 2014-06-11 | Jsr株式会社 | 着色組成物、カラーフィルタおよびカラー液晶表示素子 |
JP5835014B2 (ja) * | 2011-03-31 | 2015-12-24 | Jsr株式会社 | 画素パターンの形成方法及びカラーフィルタの製造方法 |
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