JP2021001877A - ガスセンサー及び気相検体の検知方法 - Google Patents
ガスセンサー及び気相検体の検知方法 Download PDFInfo
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- JP2021001877A JP2021001877A JP2020101887A JP2020101887A JP2021001877A JP 2021001877 A JP2021001877 A JP 2021001877A JP 2020101887 A JP2020101887 A JP 2020101887A JP 2020101887 A JP2020101887 A JP 2020101887A JP 2021001877 A JP2021001877 A JP 2021001877A
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- G01N29/02—Analysing fluids
- G01N29/022—Fluid sensors based on microsensors, e.g. quartz crystal-microbalance [QCM], surface acoustic wave [SAW] devices, tuning forks, cantilevers, flexural plate wave [FPW] devices
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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Abstract
Description
−C(=O)NHR3、−O−C(=O)R4、−NHC(=O)R5、−S(=O)2−OR6、又は−S(=O)2−NHR3から独立して選択され;R2は、H、C1〜10フルオロアルキル、C1〜10ヒドロキシアルキル、若しくはC1〜10アミノアルキルなどの、置換若しくは非置換C1〜10アルキル、C6〜20アリール、又はC4〜20ヘテロアリールから独立して選択され;R3は、H又は置換若しくは非置換C1〜10アルキルから独立して選択され;R4は、H又は、C1〜10ヒドロキシアルキルなどの、置換若しくは非置換C1〜10アルキル、−O(C1〜10アルキル)、又は−NH(C1〜10アルキル)から独立して選択され;R5は、H又は、C1〜10ヒドロキシアルキルなどの、置換若しくは非置換C1〜10アルキル、−O(C1〜10アルキル)、又は−NH(C1〜10アルキル)から独立して選択され;R6は、H又は置換若しくは非置換C1〜10アルキルから独立して選択される)
から選択される1種以上の第1モノマーと;2つ以上のシクロペンタジエノン基を含む1種以上の第2モノマーとを重合単位として含むものが挙げられる。アリール基は、1つ以上のヘテロ原子、例えば、N、O、又はSを含んでもよく、好ましいヘテロアリール基は、例えば、フラン、ピリジン、ピラジン、ピラゾール、トリアジン、オキサゾール、インドール、ベンゾフラン、カルバゾール、チオフェン、キノロン、イソキノリン、又はクロメンの1つ以上を含む。アリール基についての典型的な置換基としては、例えば、ヒドロキシ、フルオロ、アミノ、カルボキシ、チオ、又はチオカルボニルの1つ以上が挙げられる。式(1)のモノマーについては、aは、0〜2の整数であり、より好ましくは、aは、0又は1である。式(2)のモノマーについては、aは、0〜3、より好ましくは0〜2、さらにより好ましくは、0又は1の整数である。
で示される構造を有することが好ましい。好ましくは、各R7は、C3〜6アルキル、フェニル、又は置換フェニルから独立して選択され、より好ましくは、各R7はフェニルである。
のものが、第2モノマーのために特に好ましい。
各R10は、ハロゲン、C1〜6ハロアルキル、C1〜6アルコキシ、C1〜6ハロアルコキシなどの、置換若しくは非置換C1〜6アルキル、フェニル、及びフェノキシから独立して選択され;cは、0〜4の整数であり;d及びeのそれぞれは、0〜3の整数であり;各Zは、O、S、NR11、PR11、P(=O)R11、C(=O)、CR12R13、及びSiR12R13から独立して選択され;R11、R12、及びR13は、H、C1〜4ハロアルキルなどの、置換若しくは非置換C1〜4アルキル、及びフェニルから独立して選択される)
に示される構造を有するものが挙げられる。xは1又は2、より好ましくは1であることが好ましい。yは0又は1、より好ましくは1であることが好ましい。好ましくは、各R10は、ハロゲン、ハロC1〜4アルキル、C1〜4アルコキシ、ハロC1〜4アルコキシなどの、置換若しくは非置換C1〜4アルキル、及びフェニルから、より好ましくはフルオロ、C1〜4アルキル、フルオロC1〜4アルキル、C1〜4アルコキシ、フルオロC1〜4アルコキシ、及びフェニルから独立して選択される。cは0〜3、より好ましくは0〜2、その上好ましくは0又は1であることが好ましい。d及びeのそれぞれは、独立して、0〜2、より好ましくは0又は1であることが好ましい。式(6)において、d+e=0〜4、より好ましくは0〜2であることが好ましい。各Zは、好ましくは、O、S、NR11、C(=O)、CR12R13、及びSiR12R13から、より好ましくはO、S、C(=O)、及びCR12R13から、その上より好ましくはO、C(=O)、及びCR12R13から独立して選択される。各R11、R12、及びR13は、H、C1〜4アルキル、フルオロC1〜4アルキル、及びフェニルから;より好ましくはH、C1〜4アルキル、フルオロC1〜2アルキル、及びフェニルから独立して選択されることが好ましい。好ましくは、各Ar2は、式(5)を有する。
以下のポリマーA〜Eは、下記の手順を用いて合成した。数平均分子量(Mn)、重量平均分子量(Mw)及び多分散性(PDI=Mw/Mn)は、報告される場合、ポリスチレン標準を基準とするゲル浸透クロマトグラフィー(GPC)によって測定した。ポリマーFは、Dupont Electronics & ImagingによってSiLK(商標)Jポリアリーレン樹脂として販売される市販材料である。
ポリマーA
4リットルの円筒形反応器に、485.010gのジフェニレンオキシドビス(トリフェニルシクロペンタジエノン)(DPO−CPD)、27.370gの3,5−ジエチニル安息香酸(DEBzOH)、及び2422gのγ−ブチロラクトン(GBL)を室温で装入した。フラスコのトップに、次に、ドライアイス凝縮器、温度調節器付き熱電対、N2注入口、及び撹拌システムを備え付けた。反応器をぴったり合った加熱マントル中に入れた。システムを排気し、N2で3回パージして容器から空気を除去し、それをその後N2の一定流れで覆った。反応システムを次に135℃の内温に加熱した。1時間後に、システムを90℃に放冷し、引き続き、追加の300gのGBLと一緒に、第2アリコート(27.780g)のDEBzOHをフラスコに添加した。反応混合物を再び135℃に加熱し、この温度に1時間保った。システムを再び90℃に放冷し、引き続き、追加の330gのGBLと一緒に、第3アリコート(27.110g、0.25当量)のDEBzOHをフラスコに添加した。反応混合物を再び135℃に加熱し、この温度に1時間保ち、その時間後にシステムを再び90℃に放冷し、引き続き、追加の330gのGBLと一緒に、第4アリコート(30.763g、0.29当量)のDEBzOHをフラスコに添加した。反応混合物を再び135℃に加熱し、この温度に6時間保った。反応混合物を次に室温に冷却した。結果として生じたジエチル安息香酸−ビスシクロペンタジエニルポリアリーレンポリマーを、室温でイソプロパノールを添加することによりそれを溶液から沈澱させることによって反応混合物から単離し、濾過し、追加のイソプロパノールで洗浄し、その後濾過物を70℃で24時間乾燥させ、ポリマーAをもたらした。[ポリマーA:Mn=10.26kDa;Mw=21.33kDa;PDI=2.08]。
DPO−CPD(109.42g)及び1,3−ジエチニルベンゼン(18.34g)を、(TEFLON(商標)フルオロポリマー排液装置プラグ付きの、ガラス内張りの)1LのOptiMax反応器に添加した。エトキシベンゼン溶媒(309g)を添加して濃いえび茶色の不均一混合物を形成した。反応器を、OptiMax合成ワークステーション(Synthesis Workstation)に移し、窒素ガスの雰囲気下で密封した。反応器トップに、(反応器底部から1cmまで上がった)4パドル撹拌機付き撹拌棒、水冷式還流冷却器、(撹拌シャフトと反応器壁との間の中間に放射状に配置された、混合物の中央深さに置かれた)内部熱電対、及び(反応器の外壁に垂直に及び隣接して置かれた)1cmバッフルを取り付けた。反応器を25℃の内温にセットし、撹拌を100prmで開始して不均一内容物を混合した。25℃での30分の平衡期間後に、反応器を、115〜135℃の内温に達するまで、1℃/分の速度で温めた。反応器を、18時間にわたって標的温度に維持した。反応器を次に1℃/分の速度で25℃に冷却した。反応器の内容物を、次に、反応器の底部において出口を通してボトルに移し、ポリマーBをもたらした。[ポリマーB:Mn=37.02kDa;Mw=105.95kDa;PDI=2.86]。
4,4’−(オキシビス(4,1−フェニレン))ビス(3−フェニル−2,5−ビス(4−(フェニルエチニル)フェニル)シクロペンタ−2,4−ジエン−1−オン(A4B2)(200g、1当量)及び1,3−ジエチニルベンゼン(21.7g、1.02当量)を、TEFLON(商標)フルオロポリマー排液装置プラグ付きの、ガラス内張りの)1LのOptiMax反応器に添加した。アニソール溶媒を、30重量%固形分を含有する溶液を提供するための量で添加して濃いえび茶色の不均一混合物を形成した。反応器を、OptiMax合成ワークステーションに移し、窒素ガスの雰囲気下で密封した。反応器トップに、(反応器底部から1cmまで上がった)4パドル撹拌機付き撹拌棒、水冷式還流冷却器、(撹拌シャフトと反応器壁との間の中間に放射状に配置された、混合物の中央深さに置かれた)内部熱電対、及び(反応器の外壁に垂直に及び隣接して置かれた)1cmバッフルを取り付けた。反応器を25℃の内温にセットし、撹拌を100prmで開始して不均一内容物を混合した。25℃で30分の平衡期間後に、反応器を、115〜135℃の内温に達するまで、1℃/分の速度で温めた。反応器を、72時間にわたって標的温度に維持した。反応器を次に1℃/分の速度で25℃に冷却した。反応器の内容物を、次に、反応器の底部において出口を通してボトルに移し、ポリマーCをもたらした。[ポリマーC:Mn=19.6kDa;Mw=49.7kDa;PDI=2.53]。
A4B2(1当量)及びDEBzOH(1.01当量)を、TEFLON(商標)フルオロポリマー排液装置プラグ付きの、ガラス内張りの)1LのOptiMax反応器に添加した。PGMEA溶媒を、30重量%固形分を含有する溶液を提供するための量で添加して濃いえび茶色の不均一混合物を形成した。反応器を、OptiMax合成ワークステーションに移し、窒素ガスの雰囲気下で密封した。反応器トップに、(反応器底部から1cmまで上がった)4パドル撹拌機付き撹拌棒、水冷式還流冷却器、(撹拌シャフトと反応器壁との間の中間に放射状に配置された、混合物の中央深さに置かれた)内部熱電対、及び(反応器の外壁に垂直に及び隣接して置かれた)1cmバッフルを取り付けた。反応器を25℃の内温にセットし、撹拌を100prmで開始して不均一内容物を混合した。25℃で30分の平衡期間後に、反応器を、115℃の内温に達するまで、1℃/分の速度で温めた。反応器温度を18時間にわたって標的温度に維持した。反応器を次に1℃/分の速度で25℃に冷却した。反応器の内容物を次に、反応器の底部において出口を通してボトルに移し、ポリマーDをもたらした。[ポリマーD:Mn=22.0kDa;Mw=70.0kDa;PDI=3.18]。
検知ポリマー組成物は、ポリマー組成物と溶媒とを20mLのシンチレーションバイアル中で表1に示される重量百分率で組み合わせることによって調製した。混合物を、溶液が生じるまで撹拌した。
QCMガスセンサーは、Laurell WS−650MZ−8NPPBスピンコーターで、1500rpmで30秒間、表2に明記されるようにCr/Au電極(Stanford Research Systems O100RX1)付きの各1インチ水晶上に検知ポリマー組成物をスピンコートすることによって調製した。検知ポリマー層を、空気環境の場合にはホットプレート及び窒素環境の場合にはPalomar Technologies SST 1200 Table Top Furnaceを用いて表2に示される条件で硬化させた。
上記のように調製された各ポリマーフィルム被覆QCM構成部品を、結晶ホルダーに入れ、トップから4インチの深さでQCMシステムの7LのPyrex試験チャンバー中に配置した。投与前ベースライン共振周波数fpd(図5における参照A)を確立し、試験チャンバーに1μLの液相トルエン(26ppm)を投与した。検体を磁気攪拌機によって撹拌して分散させ、液体を気相でチャンバーの至る所に拡散させた。QCMを、フル応答共振周波数(図5における参照B)に達するまで投与前ベースライン共振周波数からの共振周波数シフトによって投与に応答させた。試験チャンバーを大気へガス抜きし、センサーの共振周波数を、一定の投与後ベースライン周波数(図5における参照C)に達するまで又は90分回復させた。感度は、供与前ベースライン共振周波数マイナスフル応答共振周波数として決定し、応答時間(tresp)は、フル感度応答の95%に達するまでの時間として決定した。センサーを、フィルムが調製されたその日に及び7日間の老化後に評価した。結果を表2に提供する。
角切り(1インチ×1インチ)シリコンウエハー上の薄膜のFTIRスペクトロスコピーを、Harrick Scientific Brewster角度セットアップを取り付けたThermo Scientific Nicolet iS5機器を用いて取った。全ベースラインを、ポリマー機能化ウエハーと同じウエハーからカットした未改質のむき出しシリコンウエハーから取った。スペクトルを、4000及び400cm−1の間で記録した。1480〜1522cm−1の全ピーク面積(ピーク積分)及び1648〜1690cm−1の全ピーク面積を測定した。試料についての後者ピーク面積対前者ピーク面積の比を決定し、表3に示す。
ラマンスペクトロスコピー測定を、300gr/mm回折格子付きの633nm励起を用いるHoriba LabRam HR Raman顕微鏡を用いて行った。測定は、100×対物レンズ(Olympus Mplan−100×、NA 0.9)を用いて行った。2190〜2250cm−1の全ピーク面積(ピーク積分)及び1550〜1650cm−1の全ピーク面積を測定した。試料についての前者ピーク面積対後者ピーク面積の比を決定し、表3に示す。
102 前面(すなわち、検知側)電極
103 裏面電極
104 ポリマー検知層
200 単結晶シリコンウエハー基材
202 絶縁層
204 前面(すなわち、検知側)電極
206 圧電層
208 裏面電極
210 ポリマー検知層
212 空洞
300 圧電基材(層)
302 入力相互噛合変換器(IDT)
304 出力相互噛合変換器
306 ポリマー検知層
400 基材
402 相互噛合電極(IDE)
406 ポリマー検知層
Claims (16)
- 基材;
前記基材上の複数の電極;並びに
気相検体を吸着するための前記基材上のポリマー検知層であって、その検体の前記着が、ガスセンサーからの出力信号の変化をもたらす前記ガスセンサーの特性を変化させるために有効であり、ここで、前記ポリマー検知層が、芳香族アセチレン基を含む第1モノマーと、2つ以上のシクロペンダジエノン基を含む第2モノマーとを含むモノマーの反応生成物、又は前記反応生成物の硬化生成物を含む置換若しくは非置換ポリアリーレから選択されるポリマーを含むポリマー検知層
を含む、ガスセンサー。 - 前記ポリマーが、0.15以下の1648〜1690cm−1の全ピーク面積対1480〜1522cm−1の全ピーク面積の比を有するFTIR分光スペクトルを示す、請求項1に記載のガスセンサー。
- 前記ポリマー検知層が、1.0以下の2190〜2250cm−1の全ピーク面積対1550〜1650cm−1の全ピーク面積の比を有するラマン分光スペクトルを示す、請求項2に記載のガスセンサー。
- 前記ポリマー検知層が、x線光電子分光法によって測定されるように7原子%以下の酸素含有量を有する、請求項1又は2に記載のガスセンサー。
- 前記ポリマー検知層が、前記第1モノマー、前記第2モノマー及び溶媒を含む組成物をコートする工程と、前記コートされた組成物を、不活性ガス雰囲気中で300〜400℃の温度で硬化させる工程とを含むプロセスによって形成される、請求項1〜4のいずれか一項に記載のガスセンサー。
- 前記第1モノマーが、式(1)又は式(2):
のモノマーから選択される、請求項1〜5のいずれか一項に記載のガスセンサー。 - 前記ガスセンサーが、音響波、容量性、又は電気伝導度ガスセンサーである、請求項1〜8のいずれか一項に記載のガスセンサー。
- 前記ガスセンサーが音響波ガスセンサーである、請求項9に記載のガスセンサー。
- (a)請求項1〜10のいずれか一項に記載のガスセンサーを提供する工程と;
(b)気相検体を含む雰囲気に前記ポリマー検知層を曝す工程と
を含む、気相検体の検知方法。 - 前記気相検体の吸着が、前記ガスセンサーからの出力信号の変化をもたらす前記ガスセンサーの特性を変化させるために有効である、請求項9に記載の方法。
- 順に、
(c)前記センサーにおける前記気相検体の含有量を減らすために有効な第2雰囲気に前記センサーを曝す工程と;
(d)前記音響波センサーの共振周波数をベースライン周波数に回復させる工程と;
(e)気相検体を含む第3雰囲気に前記センサーを曝す工程と
をさらに含む、請求項10に記載の方法であって、
前記工程(c)、(d)、及び(e)シーケンスが1回以上行われる方法。 - 前記気相検体が有機物質である、請求項11〜13のいずれか一項に記載の方法。
- 前記気相検体が、ベンゼン、トルエン、キシレン、メシチレン、エタノール、ホルムアルデヒド、アセトアルデヒド、アセトン、酢酸、又はトリアルキルアミンの1つ以上から選択される、請求項14に記載の方法。
- 前記気相検体が無機物質である、請求項11〜13のいずれか一項に記載の方法。
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US11906493B2 (en) | 2024-02-20 |
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