JP5700547B2 - バイオチップ形成用感光性樹脂組成物、及びバイオチップ - Google Patents
バイオチップ形成用感光性樹脂組成物、及びバイオチップ Download PDFInfo
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- JP5700547B2 JP5700547B2 JP2011120007A JP2011120007A JP5700547B2 JP 5700547 B2 JP5700547 B2 JP 5700547B2 JP 2011120007 A JP2011120007 A JP 2011120007A JP 2011120007 A JP2011120007 A JP 2011120007A JP 5700547 B2 JP5700547 B2 JP 5700547B2
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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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- 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
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Description
本発明の他の目的は、高アスペクト比、高精細なパターンを有するとともに、該パターンの基板密着性が高く、自家蛍光性が低く、しかも培養細胞に対しての損傷性が極めて低いバイオチップを提供することにある。
の何れかの基を示す]
で表される基を示す。nは0〜100の整数を示し、mは1〜100の整数を示す。mが2以上の場合、m個の括弧内の基はそれぞれ同一であっても異なっていてもよい。また、nが2以上の場合、n個のAはそれぞれ同一であっても異なっていてもよい。但し、式(1)中に少なくとも1個のAを有し、且つAのうち少なくとも1つは式(a)中のXが式(b)で表される基である]
で表されるエポキシ化合物(A1)、下記式(2)
で表される基を示す。Yは、次式(f)
で表される基を示す。qは0以上の整数、pは3以上の整数を示す。qが2以上の場合、q個の括弧内の基はそれぞれ同一であっても異なっていてもよい。また、p個の括弧内の基はそれぞれ同一であっても異なっていてもよい。但し、式(2)中に少なくとも1個のBを有する]
で表されるエポキシ化合物(A2)、光カチオン重合開始剤(B)及び溶剤(C)を含有するバイオチップ形成用感光性樹脂組成物を提供する。
エポキシ化合物(A1)は前記式(1)で表される化合物である。式(1)中、R1はm個の活性水素を有する有機化合物から活性水素を除いた残基を示し、Aは置換基を有するオキシシクロヘキサン骨格であり、前記式(a)で表される基を示す。式(a)中、Xは、前記式(b)、(c)、(d)の何れかの基を示す。式(d)中、R2は、水素原子、アルキル基、アルキルカルボニル基又はアリールカルボニル基を示す。また、式(1)中、nは0〜100の整数(好ましくは0〜30の整数)を示し、mは1〜100の整数(好ましくは1〜30の整数、さらに好ましくは1〜10の整数)を示す。mが2以上の場合、m個の括弧内の基はそれぞれ同一であっても異なっていてもよい。また、nが2以上の場合、n個のAはそれぞれ同一であっても異なっていてもよい。但し、式(1)中に少なくとも1個(好ましくは3個以上)のAを有し、且つAのうち少なくとも1つは式中のXが式(b)で表される基である。エポキシ化合物(A1)は1種単独で又は2種以上の混合物として使用できる。なお、式(1)において、Aにおける式(a)の左側の結合手がR1と結合している。
エポキシ化合物(A2)は、前記式(2)で表される化合物である。式(2)中、R3は炭素数3〜30の3価以上の脂肪族、脂環式又は芳香族カルボン酸からカルボキシル基を除いた残基を示す。Bは、前記式(e)で表される基を示す。Yは、前記式(f)で表される基を示す。式(e)中、Ra、Rbは、同一又は異なって、水素原子、メチル基又はエチル基を示す。rは4〜8の整数を示す。r個の括弧内の基はそれぞれ同一であっても異なっていてもよい。式(f)中、Rd1、Rd2、Rd3、Rd4、Rd5、Rd6、Rd7、Rd8、Rd9は、同一又は異なって、水素原子又は炭素数1〜9(好ましくは炭素数1〜4)のアルキル基を示す。また、式(2)中、qは0以上の整数(例えば、0〜100の整数、好ましくは0〜30の整数、さらに好ましくは0〜10の整数)、pは3以上の整数(例えば、3〜100の整数、好ましくは3〜30の整数、さらに好ましくは3〜10の整数)を示す。qが2以上の場合、q個の括弧内の基はそれぞれ同一であっても異なっていてもよい。また、p個の括弧内の基はそれぞれ同一であっても異なっていてもよい。但し、式(2)中に少なくとも1個のBを有する。エポキシ化合物(A2)は1種単独で又は2種以上の混合物として使用できる。
本発明において、光カチオン重合開始剤(B)としては、特に制限はなく公知の光カチオン重合開始剤を使用できる。光カチオン重合開始剤として、例えば、スルホニウム塩(スルホニウムイオンとアニオンとの塩)、ヨードニウム塩(ヨードニウムイオンとアニオンとの塩)、セレニウム塩(セレニウムイオンとアニオンとの塩)、アンモニウム塩(アンモニウムイオンとアニオンとの塩)、ホスホニウム塩(ホスホニウムイオンとアニオンとの塩)、遷移金属錯体イオンとアニオンとの塩などが挙げられる。光カチオン重合開始剤(B)は1種単独で又は2種以上を組み合わせて使用できる。
本発明において、溶剤(C)としては、特に制限はなく、1種単独で又は2種以上を混合して使用できる。溶剤(C)としては、、そのものに蛍光発光が少なく、さらに光照射時及び熱硬化時に起こる副反応で自家蛍光を発する副生成物を生成しにくい溶剤が好ましい。このような溶剤の具体例としては、例えば、アセトン、メチルエチルケトン、メチルイソブチルケトン、シクロペンタノン、シクロヘキサノンなどのケトン系溶剤、酢酸エチル、メトキシブチルアセテート、プロピレングリコールモノメチルエーテルアセテートなどのエステル系溶剤、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メチルエーテル、プロピレングリコールモノプロピルエーテル、ジプロピレングリコールモノプロピルエーテルなどの各種グリコールエーテル系溶剤が挙げられる。これらの中でも、特に蛍光物質を発生し難いことと乾燥性の観点からシクロペンタノンが好ましい。
本発明のバイオチップ形成用感光性樹脂組成物には、本発明の趣旨を損なわない範囲で、より一層の性能向上のために種々の添加剤を加えることができる。添加剤を加える場合は、添加剤自体に自家蛍光がなく、また使用される光カチオン重合開始剤(B)との反応で自家蛍光を発するような生成物を副生しないものを用いることが好ましい。このような目的で使用される添加剤としては、本発明の必須成分であるエポキシ樹脂(A)以外の光カチオン重合性化合物、界面機能付与剤、その他の添加剤などが挙げられる。
本発明のドライフィルムレジストは、ベースフィルム上に前記本発明のバイオチップ形成用感光性樹脂組成物を塗布して形成された感光性樹脂層が設けられている。さらに該感光性樹脂層の上にカバーフィルムが積層されていてもよい。
本発明におけるバイオチップとは、医療検査、食品検査に供され、細胞培養やセルソーター、生化学分析、環境分析、化学合成など種々の生化学あるいは化学プロセスを行なわせるために、基板上に数μmから数百μmの微細な流路(マイクロチャネル)やミキサーなどの素子や検出部などが設けられたものである。バイオチップには必要に応じて薬液を投入するための注入孔が設けられてもよい。
ダイセル化学工業社製、商品名「EHPE 3150」[2,2−ビス(ヒドロキシメチル)−1−ブタノールの1,2−エポキシ−4−(2−オキシラニル)シクロヘキサン付加物;固体状多官能脂環型エポキシ樹脂]50部、ダイセル化学工業社製、商品名「エポリード GT401」[エポキシ化ブタンテトラカルボン酸テトラキス−(3−シクロヘキセニルメチル)修飾ε−カプロラクトン;液状多官能脂環型エポキシ樹脂]10部、光カチオン重合開始剤(サンアプロ社製、商品名「CPI−100P」;ジフェニル[4−(フェニルチオ)フェニル]スルホニウムヘキサフルオロホスファート50%炭酸プロピレン溶液)5.5部、及びシクロペンタノン(溶剤)50部を撹拌混合して、感光性樹脂組成物を調製した。
得られた感光性樹脂組成物を、ヘキサメチルジシラザン(HMDS)を塗布したガラス基板(2cm×2cm)上にスピンコーターを用いて均一に塗布し、感光性樹脂組成物層を形成した。なお、ガラス基板表面へのHMDSの塗布(スピンコーターで塗布後にホットプレートにより80℃で5分乾燥させる)は、ガラス基板と当該エポキシ樹脂との密着性を向上させる目的がある。形成した感光性樹脂組成物層をホットプレートにより65℃で5分および95℃で20分の露光前ベークを行った。その後、露光装置(ナノテック社製、片面マスクアライナーLA310、波長350nm以上光照射)を用いてマスク転写時の精度が最良となる露光量で露光を行なった。ホットプレートにより65℃で1分および95℃で5分の露光後ベーク(PEB)を行い、日本化薬社製の現像液(商品名「SU−8 developer」)を用いて浸漬法により23℃で2分〜10分間現像処理を施し、続いてイソプロピルアルコールに23℃で1分〜5分、浸漬法にてリンスすることで、基板上に硬化した塗膜及びパターンを得た。
感光性樹脂組成物として、日本化薬社製の光硬化性エポキシ樹脂組成物(商品名「SU−8 3010」;光カチオン重合触媒含有エポキシ樹脂組成物)を用いた以外は実施例1と同様にして、基板上に硬化した塗膜及びパターンを得た。
実施例及び比較例で得られた各硬化塗膜について下記の評価を行った。結果を表1に示す。なお、下記(2)及び(3)において、培地としては、DMEM−10%FBS[DMEM(ダルベッコ変法イーグル培地;シグマ−アルドリッチ社製)に体積比で10%相当のFBS(ウシ胎児血清;シグマ−アルドリッチ社製)を添加したもの]を用いた。
日立社製分光光度計F-4500を用い、365nmで励起し最大蛍光波長領域(430nm)の蛍光強度を比較した。
表面に硬化塗膜が形成されたガラス基板を3.5cmシャーレに入れて60℃で36時間殺菌処理を施した。100%コンフルまで培養したMIN6−m9細胞から細胞懸濁液(2.5×105 cells/ml)を調製し、各板が入った3.5cmシャーレに1ml、培地2.5mlを滴下した。続いて5%CO2インキュベータに入れて培養し、1日ごとに塗膜の様子を撮影し、耐剥離性を評価した。
表面に硬化塗膜が形成されたガラス基板を3.5cmシャーレに入れて60℃で36時間殺菌処理を施した。100%コンフルまで培養したMIN6−m9細胞から細胞懸濁液(2.5×105 cells/ml)を調製し、各板が入った3.5cmシャーレに1ml、培地2.5mlを滴下した。続いて5%CO2インキュベータに入れて培養し、1日ごとに細胞の様子を撮影した。撮影結果から細胞の増殖速度と形態を比較して細胞への損傷性を評価した。細胞培養開始1日目の結果を表1に示す。
なお、対照(参考例1)として、表面に硬化塗膜が形成されたガラス基板の代わりに、2cm×2cmのガラス基板(表面に酸素プラズマ処理を施している)を用いた以外は上記と同様にして細胞を培養した。
Claims (7)
- 下記式(1)
の何れかの基を示す]
で表される基を示す。nは0〜100の整数を示し、mは1〜100の整数を示す。mが2以上の場合、m個の括弧内の基はそれぞれ同一であっても異なっていてもよい。また、nが2以上の場合、n個のAはそれぞれ同一であっても異なっていてもよい。但し、式(1)においてAの総数は1以上であり、且つAのうち少なくとも1つは式(a)中のXが式(b)で表される基である]
で表されるエポキシ化合物(A1)、下記式(2)
で表される基を示す。Yは、次式(f)
で表される基を示す。qは0以上の整数、pは3以上の整数を示す。qが2以上の場合、q個のBはそれぞれ同一であっても異なっていてもよい。また、p個の括弧内の基はそれぞれ同一であっても異なっていてもよい。但し、式(2)中に少なくとも1個のBを有する]
で表されるエポキシ化合物(A2)、光カチオン重合開始剤(B)及び溶剤(C)を含有するバイオチップ形成用感光性樹脂組成物。 - エポキシ化合物(A1)とエポキシ化合物(A2)の含有比率が、前者/後者(重量比)=1/99〜99/1である請求項1記載のバイオチップ形成用感光性樹脂組成物。
- 光カチオン重合開始剤(B)が、トリアリールスルホニウム塩である請求項1又は2記載のバイオチップ形成用感光性樹脂組成物。
- 溶剤(C)が、ケトン系溶剤、エステル系溶剤及びグリコールエーテル系溶剤からなる群より選択された少なくとも1種の溶剤である請求項1〜3の何れか1項に記載のバイオチップ形成用感光性樹脂組成物。
- ベースフィルム上に請求項1〜4の何れか1項に記載のバイオチップ形成用感光性樹脂組成物を塗布して形成された感光性樹脂層が設けられているか、又は、さらに該感光性樹脂層の上にカバーフィルムが積層されていることを特徴とするドライフィルムレジスト。
- 第1の基板上に請求項1〜4の何れか1項に記載のバイオチップ形成用感光性樹脂組成物を塗布して形成された感光性樹脂層をフォトリソグラフィーに付してパターンを形成し、該パターン上に第2の基板を積層して得られるバイオチップ。
- 基板上に請求項1〜4の何れか1項に記載のバイオチップ形成用感光性樹脂組成物を塗布して形成された感光性樹脂層をフォトリソグラフィーに付してパターンを形成し、該パターン上に、請求項5記載のドライフィルムレジストを、該ドライフィルムレジストの感光性樹脂層が前記パターンと接するようにして積層し、さらに該感光性樹脂層をフォトリソグラフィーに付してパターンを形成して得られるバイオチップ。
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JP2011120007A JP5700547B2 (ja) | 2011-05-30 | 2011-05-30 | バイオチップ形成用感光性樹脂組成物、及びバイオチップ |
EP12793730.8A EP2717097A4 (en) | 2011-05-30 | 2012-05-16 | LIGHT-SENSITIVE RESIN COMPOSITION FOR FORMING BIOCHIPS AND BIOCHIP |
KR1020137032860A KR20140034820A (ko) | 2011-05-30 | 2012-05-16 | 바이오 칩 형성용 감광성 수지 조성물 및 바이오 칩 |
CN201280023489.3A CN103534647A (zh) | 2011-05-30 | 2012-05-16 | 用于形成生物芯片的感光性树脂组合物以及生物芯片 |
US14/119,724 US20140099243A1 (en) | 2011-05-30 | 2012-05-16 | Photosensitive resin composition for forming biochip, and biochip |
PCT/JP2012/062483 WO2012165143A1 (ja) | 2011-05-30 | 2012-05-16 | バイオチップ形成用感光性樹脂組成物、及びバイオチップ |
TW101119047A TW201303496A (zh) | 2011-05-30 | 2012-05-29 | 生物晶片形成用感光性樹脂組成物及生物晶片 |
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EP (1) | EP2717097A4 (ja) |
JP (1) | JP5700547B2 (ja) |
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JP6471490B2 (ja) * | 2014-12-24 | 2019-02-20 | 三菱ケミカル株式会社 | ドライフィルムレジスト用保護フィルムおよび感光性樹脂積層体 |
JP6878115B2 (ja) * | 2017-04-25 | 2021-05-26 | オリエンタル酵母工業株式会社 | 低蛍光性実験動物用飼料およびその製造方法 |
BR112020026299B1 (pt) | 2018-07-20 | 2024-03-05 | Illumina Cambridge Limited | Composição de resina, célula de fluxo e método para fazer uma célula de fluxo |
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US4231951A (en) | 1978-02-08 | 1980-11-04 | Minnesota Mining And Manufacturing Company | Complex salt photoinitiator |
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JP2926262B2 (ja) | 1990-07-10 | 1999-07-28 | ダイセル化学工業株式会社 | 新規な脂環式化合物からなる組成物およびその製造方法 |
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US6602651B1 (en) * | 1998-07-07 | 2003-08-05 | Kansai Paint Co., Ltd. | Water-based solder resist composition |
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JP2004133424A (ja) * | 2002-08-30 | 2004-04-30 | Toyo Gosei Kogyo Kk | パターン形成用感放射線ネガ型レジスト組成物およびパターン形成方法 |
DE10310615B3 (de) * | 2003-03-10 | 2004-11-04 | Infineon Technologies Ag | Verfahren zur Herstellung eines Biochips und Biochip |
US20050260522A1 (en) | 2004-02-13 | 2005-11-24 | William Weber | Permanent resist composition, cured product thereof, and use thereof |
JP4292405B2 (ja) | 2004-02-16 | 2009-07-08 | Jsr株式会社 | 検査素子用のチップ基板およびその製造方法 |
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JP2009075261A (ja) | 2007-09-19 | 2009-04-09 | Nippon Kayaku Co Ltd | 感光性樹脂組成物、及びそれを用いて得られたマイクロチップ |
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- 2012-05-16 WO PCT/JP2012/062483 patent/WO2012165143A1/ja active Application Filing
- 2012-05-16 CN CN201280023489.3A patent/CN103534647A/zh active Pending
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TW201303496A (zh) | 2013-01-16 |
EP2717097A4 (en) | 2015-01-14 |
US20140099243A1 (en) | 2014-04-10 |
KR20140034820A (ko) | 2014-03-20 |
CN103534647A (zh) | 2014-01-22 |
EP2717097A1 (en) | 2014-04-09 |
WO2012165143A1 (ja) | 2012-12-06 |
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