JP5431225B2 - アルカリ現像性感光性樹脂組成物、及びこれを用いて形成した表示素子向け隔壁、並びに表示素子 - Google Patents
アルカリ現像性感光性樹脂組成物、及びこれを用いて形成した表示素子向け隔壁、並びに表示素子 Download PDFInfo
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- JP5431225B2 JP5431225B2 JP2010075758A JP2010075758A JP5431225B2 JP 5431225 B2 JP5431225 B2 JP 5431225B2 JP 2010075758 A JP2010075758 A JP 2010075758A JP 2010075758 A JP2010075758 A JP 2010075758A JP 5431225 B2 JP5431225 B2 JP 5431225B2
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
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Classifications
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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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/201—Filters in the form of arrays
-
- 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
-
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- Physics & Mathematics (AREA)
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- Optics & Photonics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Epoxy Resins (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
(1)撥インク剤としての含フッ素樹脂(A)と、波長300〜450nmの紫外光に反応するアルカリ現像可能な感光性成分とを含んだアルカリ現像性感光性樹脂組成物であって、含フッ素樹脂(A)が、下記一般式(2)で表されるランダム又はブロック共重合体であると共に、平均分子量Mwが2000〜20000の範囲であり、溶剤を除いた合計成分100質量部に対する含フッ素樹脂(A)の割合が、0.05〜1質量部であることを特徴とするアルカリ現像性感光性樹脂組成物。
CH2=C(Rn)−COO−Y−O−Rf (3)
〔式中、Rnは水素またはメチル基を示し、Yはフッ素原子を含まない2価の有機基を示し、Rfは、式(1)のフッ素含有基である。〕
攪拌機を備えた内容積1リットルの反応器に、表1に示す単量体、重合開始剤、及び連鎖移動剤を仕込み、さらに固形分濃度が40質量%となるようにプロピレングリコールモノメチルアセテート(PGMEA)を加え、窒素雰囲気下に攪拌しながら、90℃にて14時間重合させた。降温後、固形分濃度が20質量%になるようにPGMEAにて希釈して、含フッ素樹脂A-1〜A-6、a-1、及びa-2の溶液を得た。重量平均分子量は、テトラヒドロフランを展開溶媒としたGPCにより求めた(ポリエチレングリコール換算)。なお、表1に示した各成分の欄に記した数値の単位は「g」である。また、含フッ素基重量(%)は、平均分子量より一分子中に含まれるフッ素原子の理論重量を仕込み比より算出して求めた値である。更に、表1中の略語の意味は次のとおりである。
CF9PEMA:CH2=C(CH3)COOCH2CH2OCOC6H4OC9F17
2-HEMA:2−ヒドロキシブチルメタクリレート
4-HBMA:4−ヒドロキシブチルメタクリレート
MMA:メタクリル酸メチル
IBMA:イソボルニルメタクリレート
4-HBAGE:4−ヒドロキシブチルアクリレートグリシジルエーテル
AIBN:アゾビスイソブチロニトリル
LM:ラウリルメルカプタン
上記「合成例A-1〜A-6、比較合成例a-1、a-2」で準備した含フッ素樹脂(A)について、それぞれ20質量%PGMEA溶液100gに対して、2−アクリロイルオキシエチルイソシアネート(Mw=141.12)を、イソシアネート基/含フッ素樹脂(A)中のヒドロキシル基=0.5mol/molとなるように加え、さらに、1,4-ジアザビシクロ[2,2,2]オクタン0.03gとを混合し、50℃にて12時間攪拌して、室温へ冷却した。得られた各ポリマー溶液A-1s〜A-6s、a-1s、及びa-3sは、IRによりNCO吸収(2730cm-1)の消失を確認した。
まず含フッ素樹脂(A)成分を除く(B)〜(F)成分ならびにYX-4000H(昭和シェル製;テトラメチルジフェニルエポキシ樹脂)を表2及び表3に記載した割合(重量部)で混合し、プロピレングリコールモノメチルエーテルアセテートを加えて固形分濃度20質量%となるようにした。引き続き、表2及び表3に記載の質量部で(A)成分溶液を加えた。次いで、2μmのポリプロピレン製メンブレンフィルターを用いて0.2kg/cm2加圧にてろ過し、アルカリ現像感光性樹脂組成物を調製した。表2及び表3において、(B)成分の( )内に、全固形分に対する配合割合を質量%で示した。また、(E)成分の配合割合については、全固形分に対する(顔料/全固形分)質量%として別欄に示した。更に、表2及び表3中の略語の意味は次のとおりである。
(B)-2:重量平均分子量30000、酸価100(KOHmg/g)のN−エチルマレイミド/メタクリル酸/ベンジルメタクリレート共重合体のプロピレングリコールモノメチルエーテルアセテート溶液(樹脂固形分濃度=36.7重量%)(N−エチルマレイミド:メタクリル酸:ベンジルメタクリレート=29:20:51mol%)
(C)-1: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との混合物(日本化薬社製 商品名 DPHA)
(D)-1:IRGACURE OXE-02 (チバ・スペシャルティ・ケミカルズ社製)
(D)-2:IRGACURE OXE-01 (チバ・スペシャルティ・ケミカルズ社製)
(E)-1:カーボンブラック濃度20重量%、高分子分散剤濃度5重量%のプロピレングリコールモノメチルエーテルアセテート分散液(固形分25%)
(F)-1:シランカップリング剤 S-510 (チッソ(株)製)
塗布異物:スピンコート後の塗膜に放射状スジが観察された場合を×<不良>、観察されなかった場合を○<良好>とした。
現像性:現像後の画素パターンを顕微鏡観察し、基板に対する剥離やパターンエッジ部分のギザツキが認められないものを○<良好>、認められるものを×<不良>と評価した。
塗膜表面粗度:現像、熱焼成後の塗膜の表面粗度(Ra)の値が、150Å未満を○<良好>、150Å以上を×<不良>と評価した。
パターン密着性:ピーリングテストで20μmパターンの剥がれが認められないものを○<良好>、認められるものを×<不良>と評価した。
PCT密着性:ポストベーク実施済みのパターン形成基板を、121℃、100%RH、2atm、及び24時間の条件下においてPCT(プレッシャー・クッカー)テストを実施後、20μmパターン部にセロハンテープを貼り付けピーリングテストを行うことでパターン密着性を評価した。
OD測定:(E)成分として黒色顔料を混合した場合、ポストベーク後2.1μmの塗膜を用いて、大塚電子社製OD計を用いて測定し、1μmあたりのOD値として記載した。
接触角測定:前述した同様の方法により、現像後にガラス基板上に10mm×10mm×2.1μmの四角パターンを形成した。この塗膜上の静的接触角をブチルカルビトールアセテート(BCA)を用いて測定した。この静的接触角が40°以上のときは○<良好>、40°未満の場合は×<不良>と評価した。
IJ(インクジェット)インキ塗布特性:この得られたマトリックス中にむかって、東芝テック製インクジェットヘッドを用い、粘度10mPa.sec、固形分濃度20%のカラーフィルター用グリーンインキを以下のように打ち込み、80℃にて1分間乾燥後、さらに230℃にてポストベークを行い、光学顕微鏡で塗工状態を観察した。
描画条件1:350×180μm画素ガラス上の中央部に42plのグリーンインキを滴下した。この時、撥インキ剤が無添加の比較例と同等のガラス面上での液広がりを示すものを○とした。
描画条件2:ポストベーク後平均膜厚保が1.8μmとなるようにグリーンインキをマトリックス中に滴下し、ポストベーク後に、マトリックス近くで光漏れが発生しているか、またはマトリックス上にインキ乾燥残りがあるか観察した。
Claims (8)
- 撥インク剤としての含フッ素樹脂(A)と、波長300〜450nmの紫外光に反応するアルカリ現像可能な感光性成分とを含んだアルカリ現像性感光性樹脂組成物であって、
含フッ素樹脂(A)が、下記一般式(2)で表されるランダム又はブロック共重合体であると共に、平均分子量Mwが2000〜20000の範囲であり、溶剤を除いた合計成分100質量部に対する含フッ素樹脂(A)の割合が、0.05〜1質量部であることを特徴とするアルカリ現像性感光性樹脂組成物。
- 前記含フッ素樹脂(A)と、(B)1分子中に酸性基と2つ以上のエチレン性二重結合とを有するアルカリ現像性オリゴマーと、(C)1分子中に3個以上のエチレン性二重結合を有する光重合性モノマーと、(D)光重合開始剤とを含有する請求項1に記載のアルカリ現像性感光性樹脂組成物。
- 前記(B)成分は、下記一般式(4)で表されるビスフェノール類から誘導される2個のグリシジルエーテル基を有したエポキシ化合物と(メタ)アクリル酸との反応物を、更に多塩基酸カルボン酸又はその無水物と反応させて得られたアルカリ現像性不飽和基含有オリゴマーである請求項2記載のアルカリ現像性感光性樹脂組成物。
- 請求項1〜3のいずれかに記載のアルカリ現像性感光性樹脂組成物に対して、(E)黒色有機顔料、混色有機顔料及び遮光材からなる群から選ばれた少なくとも1種を分散してなる遮光性分散液を添加すると共に、全固形分100質量部に対して、前記(E)成分が25〜60質量部の割合で配合されていることを特徴とする遮光性のアルカリ現像性感光性樹脂組成物。
- 請求項4に記載の表示素子向け隔壁形成用の感光性樹脂組成物。
- 請求項5に記載のカラーフィルター隔壁形成用の感光性樹脂組成物。
- 請求項5又は6に記載の感光性樹脂組成物を基板上に塗布し、乾燥した後、(a)紫外線露光装置による露光、(b)アルカリ水溶液による現像、及び(c)熱焼成の各工程を必須として得られる隔壁であって、膜厚が1.5〜3μmであることを特徴とする表示素子向け隔壁。
- 請求項7に記載の隔壁内にインクジェット印刷法により画素を形成したことを特徴とする表示素子。
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TW100105791A TWI516866B (zh) | 2010-03-29 | 2011-02-22 | An alkali-developable photosensitive resin composition, and a spacer for a display element formed therefrom, and a display element |
KR1020110026669A KR101787651B1 (ko) | 2010-03-29 | 2011-03-25 | 알칼리 현상성 감광성 수지 조성물, 및 이것을 이용해서 형성한 표시소자용 격벽, 그리고 표시소자 |
CN201110080483.7A CN102207681B (zh) | 2010-03-29 | 2011-03-29 | 碱显影性感光性树脂组合物、及使用其而形成的适合显示元件的间壁、以及显示元件 |
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KR101000360B1 (ko) * | 2008-09-22 | 2010-12-13 | 롬엔드하스전자재료코리아유한회사 | 현상 가능한 초소수성 감광성조성물 |
JP5180765B2 (ja) * | 2008-10-02 | 2013-04-10 | 新日鉄住金化学株式会社 | アルカリ現像感光性樹脂組成物及びこれを用いて形成した表示素子隔壁並びに表示素子 |
JP5329192B2 (ja) * | 2008-11-27 | 2013-10-30 | 東京応化工業株式会社 | 感光性樹脂組成物 |
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