JP2007527114A - ペリレンn型半導体及び関連装置 - Google Patents
ペリレンn型半導体及び関連装置 Download PDFInfo
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- JP2007527114A JP2007527114A JP2006551415A JP2006551415A JP2007527114A JP 2007527114 A JP2007527114 A JP 2007527114A JP 2006551415 A JP2006551415 A JP 2006551415A JP 2006551415 A JP2006551415 A JP 2006551415A JP 2007527114 A JP2007527114 A JP 2007527114A
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Abstract
Description
米国政府は、登録番号N00014-02-0909(0650-300-F445)及びN00014-02-1-0381(海軍研究事務所からノースウエスタン大学に)、DARPA登録番号MDA972-03-1-0023及び登録番号DMR-0076097(MRC)(国立科学財団からノースウエスタン大学に)に準じて、この発明の一定の権利を有する。
本発明の他の目的は、本発明の化合物のいずれか1以上を、限定されないが、有機発光ダイオード、電界効果トランジスタ及び光電子デバイスを含む一連のデバイス構造に取り込むことである。
トルエン中の中性分子の基底状態の吸収及び発光スペクトルを図1に示す。これらの発色団のそれぞれの強度吸収最高値は500nm近傍であり、未置換PMI(512nm)及びPDI(526nm)のそれらに対する波長はわずかにシフトしている。これら剛性芳香族分子のぞれぞれに存在する通常の振電数列(progression)に加えて、CNPMIのスペクトルは、420nmにさらなるバンドを示し、これは、1,6-ビスフェノキシ化(phenoxylated)されたPMI誘導体に特有のものである。420nmバンドは450nmでのCNPMIの第2の振電バンドを部分的に不明瞭にする。シアノ化誘導体は、量子収率φF>0.8で全て蛍光を発し、ローダミン640(表1)に対して測定される。これらの分子の吸収及び発光特性は、ソルバトクロミックでなく、高蛍光量子収率と相まって、それらの最低励起単一状態が、電化輸送特性をほとんど又は全く備えていないことを示唆する。最低励起単一状態のエネルギー(ES)は、それぞれ、それらの吸収及び発光最大値、λabs及びλkemのエネルギーを平均することによって概算した。
(式中、L及びWは、それぞれ、デバイスのチャネル長及び幅、Ciは絶縁体容量(300nmのSiO2で1×10-8F/cm2)である。)
移動度(μ)及び閾値電圧(Vt)は、VG対(Isd)1/2(Vsd=−100Vにて)のプロットの直線部位のスロープ及び線分のそれぞれから算出することができる。これらのデータから、0.1cm2/Vsに近づくn型移動度、105の電流オン/オフ比及び〜14VのVtを、真空中、N2雰囲気中で得た。空気中での駆動で、0.05cm2/Vsの移動度を得た。成膜及び材料精製を最適化することにより、非常に高い移動度を与えるであろう。
以下の非限定的な例とデータは、本発明の化合物、デバイス及び方法に関する種々の観点及び特性を例示し、n型半導体として、及び/又は電界効果トランジスタデバイスとともに、種々のモノ及びジイミド、N−及びコア−置換ペリレン及び/又はナフタレン化合物の使用を含む。そのような置換化合物は、ここに記述される合成方法によって入手できる。本発明の有用性は、いくつかのそのような化合物の使用によって示されるとともに、類似の結果が、商業的に利用できられるか又は文献に記載されたように、及びここで与えられた置換によって又は既知の試薬及びそのような合成法の直接的な変更を用いて、種々のほかの化合物、置換基及び/又は置換パターンで、前駆化合物によって、本発明を認識する当業者によって容易に理解されるため、得ることができることは当業者によって理解されるであろう。
1Hの核磁気共鳴スペクトルは、内部標準としてTMSを用いたバリアン400MHzのNMR分光計で記録した。レーザー脱離マススペクトルは、2−ヒドロキシ−1−ナフトエ酸又はディスラノールマトリックスを用いたパーセプティブ・バイオシステムズ(Perseptive BioSystems)飛行時間型のMALDIマス分析計で得た。
吸収測定は、0.2cmの経路長キュベットを用いた島津分光光度計(UV−1601)で測定した。蛍光量子収量は、1cmの経路長キュベットを有するPTI光子−カウント分光蛍光計で得られた修正スペクトルを用いた各化合物及びローダミン640から蛍光放出バンドを集積することによって得た。各サンプルの吸収は、励起波長で0.1未満であった。
電気化学的測定は、CHインスツルメンツ・モデル660A電気化学的ワークステーションを用いて行った。溶媒は、0.1Mのテトラ−n−ブチルアンモニウム過塩素酸塩又はヘキサクロロホスフェート電解質を含むブチロニトリルであった。直径1.0mmのプラチナディスク電極、プラチナワイヤカウンター電極及びAg/AgxO参照電極を用いた。フェロセン/フェロシニウム(Fc/Fc+、0.52対SCE)を、全測定の内部参照として用いた。
分光電気化学測定を、図10で例示された自家製のクォーツセルで行った。セルは、テフロンビーカーの底にはめ込まれた1mm経路長の長方形のねじぶた付き分光測光用のキュベットからなる。プラチナガーゼは、100メッシュ、直径0.07mmのワイヤによる織布であり、透明なワーキング電極として用いた。電極を、1mmの分光測光用セルに載置し、プラチナワイヤによって出力される定電位電解装置(660A CH Instruments Model)に接続した。プラチナワイヤ・カウンター及び銀ワイヤ参照電極を、テフロン容器に載置し、それはブチロニトリル中0.1Mのテトラ−n−ブチルアンモニウム過塩素酸塩又はヘキサフルオロホスフェート溶液を保持する。電気化学的ワークステーションは、ワーキング電極の電位を制御し、島津1610A UV−VIS分光計は、レドックス種の吸収スペクトルを得た。全ての電気化学的測定を、アルゴン雰囲気下で行った。サンプルの一連の吸収スペクトルを、電位誘発スペクトル発展が完了するまで行い、それに通常7、8分かかった。
N,N-ビス(シクロヘキシル)-1,7-ジシアノ-ペリレン-3,4:9,10-ビス(ジカルボキシイミド)(CN2PDI)
N,N-ビス(シクロヘキシル)-1,7-ジブロモ-ペリレン-3,4:9,10-ビス(ジカルボキシイミド)(0.048 g、0.07 mmol)、シアン化亜鉛(0.065 g、0.55 mmol)、1,1'−ビス(ジフェニルホスフィノ)-フェロセン(0.005 g、0.01 mmol)及びトリス(ジベンジリデンアセトン)-ジパジウム(0)(0.010 g、0.01 mmol)を4mlのp−ジオキサン中に混合し、窒素雰囲気下で19時間還流した。粗生成物をクロロホルムで希釈し、セライトでろ過し、溶媒をロータリーエバポレーターで除去した。粗生成物を、98%DCM/2%アセトンを溶離液として用いたシリカカラムでクロマトグラフ法にかけ、0.041gのCN2PDI(理論値0.041 g、定量)を収量した。
M.S.(EI):計算値 C38H28N4O4: 604.2105、 実測値:604.2108。
N-(2,5-ジ-tert-ブチルフェニル)-9-シアノ-1,6-ビス(3,5-ジ-tert-ブチルフェノキシ)-ペリレン-3,4-ジカルボキシミド(CNPMI)
N-(2,5-ジ-tert-ブチルフェニル)-9-ブロモ-1,6-ビス(3,5-ジ-tert-ブチルフェノキシ)-ペリレン-3,4-ジカルボキシミド(0.100 g、0.10 mmol)、シアン化亜鉛(0.047 g、0.40 mmol)、1,1'−ビス(ジフェニルホスフィノ)-フェロセン(0.009 g、0.02 mmol)及びトリス(ジベンジリデンアセトン)-ジパジウム(0)(0.003 g、0.003 mmol)を、25ml丸底フラスコ中で、10mlのp−ジオキサン中に混合し、加熱し、窒素雰囲気下で36時間還流した。室温に冷却し、粗反応混合物をクロロホルムで希釈し、水で2回洗浄し、溶媒をロータリーエバポレーターで除去した。粗生成物を、65%ヘキサン/35%クロロホフム混合液を溶離液として用いたシリカカラムでフラッシュ・クロマトグラフ法にかけ、0.094gの生成物を利用可能にした(理論値0.094 g、定量)を収量した。
M.S.(EI): 計算値C65H70N2O4:942.5330、実測値:942.5320。
N-(2,5-ジ-tert-ブチルフェニル)-1,6,9-トリシアノ-ペリレン-3,4-ジカルボキシイミド(CN3PMI)
N-(2,5-ジ-tert-ブチルフェニル)-1,6,9-トリブロモ-ペリレン-3,4-ジカルボキシイミド (0.082 g、0.11 mmol)、シアン化亜鉛(0.156 g、1.33 mmol)、1,1'−ビス(ジフェニルホスフィノ)-フェロセン(0.009 g、0.02 mmol)及びトリス(ジベンジリデンアセトン)-ジパジウム(0)(0.004 g、0.004 mmol)を5mlのp−ジオキサンに加え、加熱し、窒素雰囲気下で16時間還流した。反応混合物を塩化メチレンで希釈し、セライトでろ過紙、溶媒をロータリーエパポレーターで除去した。粗生成物を溶離液として塩化メチレンを用いたシリカカラムでフラッシュクロマトグラフィーにかけ、0.062gのCN3PMI(理論値0.064 g、97 %)を得た。
M.S.(EI):計算値 C39H28N4O2: 584.2207、実測値:584.2199。
酸化試験
大気酸素条件下、DMF中の10-5MのCN2PDI溶液を、キュベット中に載置し、島津1601の紫外−可視光線スペクトロメータでスペクトルを記録した。図11中の実線がそのスペクトルである。乾燥窒素を15分間にわたってキュベットにバブリングした。スペクトルを3分毎に記録し、図12中に、破線及び二点は線で付したトレースを連続的に示した。最大の強度バンドはキュベットへのN2パージングの15分後に、691nmに現れた。
N,N'-ビス(1H,1H-パーフルオロブチル)-1,7-ジブロモ-ペリレン-3,4:9,10-ビス(ジカルボキシイミド)の合成
1,7-ジブロモペリレン-3,4:9,10-テトラカルボキシジアンヒドリド試薬を文献にしたがって製造した(Ahrensら、J. Am. Chem. Soc., 2004, 126, 8284-8236参照)。ジブロモ化合物(0.920 g、1.67 mmol)を20mlの1-メチル-2-ピロリジノン(NMP)と混合し、20分間超音波処理バスに載置した。次いで、15mlのNMP中の2,2,3,3,4,4,4-ヘプタフルオロブチルアミン(フルオロケミカルズ(Fluorochemicals)/SynQuest Labs)を加え、続いて酢酸(0.684 g、mmol)を添加した。反応混合物を、N2雰囲気下で4時間、85〜90℃に加熱した。内容物を室温に冷却し、200mlのメタノールに注ぎ、一晩、−10℃のフリーザー中に載置した。赤色沈殿物をろ過によって回収し、N2スチーム下で乾燥し、シリカ(クロロホルム)でクロマトグラフィーにかけ、ビス(パーフルオロ)化合物(1)(1.196 g、78 %)を得た。
M.S.: 912.51 (計算値909.88)。
N,N'-ビス(1H,1H-パーフルオロブチル)-(1,7 & 1,6)-ジシアノ-ペリレン-3,4:9,10-ビス(ジカルボキシイミド)の合成
N,N'-ビス(1H,1H-パーフルオロブチル)-1,7-ジブロモ-ペリレン-3,4:9,10-ビス(ジカルボキシイミド)(1.196 g、1.31 mmol)、シアン化亜鉛(1.264 g、10.8 mmol)、1,1'−ビス(ジフェニルホスフィノ)-フェロセン(0.119 g、0.21 mmol)及びトリス(ジベンジリデンアセトン)-ジパジウム(0)(0.0041 g、0.004 mmol)を、20mlのp−ジオキサンに加え、窒素雰囲気下で12時間還流した。反応混合物をクロロホルムで希釈し、セライトでろ過紙、溶媒をロータリーエパポレーターで除去した。得られた粗生成物を溶離液として98%DCM/2%アセトンを用いたシリカでクロマトグラフィーにかけ、ジシアノ化合物(2)(0.845 g、80 %)を得た。生成物をさらに高真空傾斜温度昇華によってさらに精製した。
M.S.: 804.42 (計算値804.05)。
実測値C, 50.76, H, 1.34, N, 6.91。
トップコンタクト形状の気相蒸着OFETを以下の方法で製造した。PDI−FCN2及びPDI−CN2の膜(〜50nmの膜厚)を、熱的に成長させたSiO2誘電体層300nmを有するn+−ドープSi(100)ウェハに、気相蒸着した(0.2Ås-1、P〜10-6Torr)。40nmの金電極を、膜堆積の前に、1,1,1,3,3,3-ヘキサメチルジシラサン蒸気で処理した。膜堆積中の基板温度を、カートリッジヒーターで変化させた。
PDI−CN2及びPDI−FCN2膜のTGA、SEM、AFM及びXRD結果を図15〜18にそれぞれ示す。
N,N'-ビス(n-オクチル)-(1,7 & 1,6)-ジブロモペリレン-3,4:9,10-ビス(ジカルボキシイミド)(1.318 g、1.71 mmol)及びシアン化銅(I)(1.550 g、17.31 mmol)を、20mlの乾燥DMFとともに、50mlの丸底フラスコ中で混合した。この混合物を、30分間、超音波処理バスに載置し、次いで、窒素雰囲気下、5時間、130℃に加熱した。次いで、DMFを減圧下で除去し、赤茶残渣を得た。クロロホルムでの36時間のソックレー抽出で、表記化合物を赤色粉末として、69%の収率で得た(0.777 g、1.17 mmol)。
1H NMR (CDC13) 報告された集大成は、1,7異性体(〜90%純度)であり、([ ]は1,6又は1,7異性体を示す): ( 9.700 (d, J = 8.2 Hz, [1,7 (1,6溶解不可能)] 2H), 9.023 (s, [1,6]), 8.972 (s, [1,7], 2H), 8.924 (d, J = 8.2 Hz, [1,7], 2H), 8.863 (d, J = 8.2 Hz, [1,6]), 4.219 (m, 4H), 1.763 (m, 4H), 1.45 - 1.20 (m, 20H), 0.884 (t, J = 6.7 Hz, 6H)。(ジカルボキシイミドを、Ulrikeら、J. Mat. Chem. (2001), 11(7), 1789-1799の方法に従って製造した)
PDI−8CN2(N−オクチル)の電子求引性特性は、530nmで最大吸収、547nmで最大発光、第1還元電位−0.1対S.C.E、〜6.6eVでHOMO及び〜4.3eVでLUMO(対真空レベル)を判別し、PDI−CN2(N−シクロヘキシル)のそれと実質的に区別不能である。PDI−8CN2の減圧(5トル)TGAは、その材料が〜325℃で10%未満の分解で蒸発することを示す。同時に、得られたDTAデータは、〜300℃での蒸発の前に固−液移行を示す。
PDI−8CN2膜を、PDI−CN2及びPDI−FCN2での研究で用いたのと類似の基板上に蒸着によって堆積した。トップコンタクト形状で金電極を前述と同様に堆積した。
トランジスタは、前述のように特徴づけられた。基板温度を90℃より高い温度で堆積することにより、0.2cm2V-1s-1と高い移動度を観察した。デバイスは、〜−6Vの閾値電圧及び104と高いION/IOFF比を有する(図19参照)。また、これらのデバイスは、不活性及び大気雰囲気下の双方で、無視できる差異で駆動する。
以下の表3に関して、この実施例は、本発明によって有効なタイプのペリレン化合物、材料及び/又は膜を例示する。そのような化合物は、部分I及び/又はJと、少なくとも1つの置換基ならびにA〜H及びK〜Lのいずれか1つの部位とを含むことができる。そのようなN−及びコア置換化合物は、当業者に理解されるように、ここに記載された合成技術によって、又はそれらの直接的な改変によって入手可能である。実施例6を参照すると、記載したイミドの製造は、アミン試薬及び対応一又は二無水物原料によってのみ限定される。例えば、I及び/又はJは、それぞれアミノ終端アルキル試薬又はエチレングリコールオリゴマーの使用によって、アルキル(置換又は未置換)又はポリエーテル部分とすることができる。同様に、芳香族アシル化、アルキル化及び/又は当該分野で公知の置換反応(例えば、米国特許第6585914号に記載された銅触媒化フルオロアルキル置換反応、全趣旨を参照することによりここに取り込む)のバリエーションを用いて、種々のコア置換基を、市販のペリレン無水物又はそれらのブロモ置換アナログにおける化学によって導入することができる。類似した方法で、N−及びコア置換ナフタレン化合物に匹敵する一連の化合物が、対応する原料及び試薬から入手可能である。
Claims (20)
- A、D、E、H、K及びLの少なくとも1つは、前記置換基及び前記部位の1つである請求項1の化合物。
- 前記置換基が、フッ素及びハーメットσ+値0.3以上の置換基から選択され、前記部分がアルキル、シクロアルキル及びアリールから選択される請求項2の化合物。
- A、D、E、H、K及びLの少なくとも1つがシアノ置換基である請求項3の化合物。
- I及びJの少なくとも1つが、Cnアルキル及びハロ置換アルキル部分から選択される請求項1の化合物。
- nが、約3から約16の範囲である請求項5の化合物。
- I及びJが、独立して、Cnアルキル及びフルオロ置換アルキル部分から選択され、A、D、E、H、K及びLの少なくとも1つが、シアノ置換基である請求項6の化合物。
- I及びJは、Cnアルキル及びハロ置換アルキル部分から選択され、nが、約3から約16の範囲である請求項8の化合物。
- 化合物は、ジシアノ置換されてなる請求項9の化合物。
- A及びDは、シアノ置換基である請求項11の化合物。
- G及びHは、シアノ置換基である請求項11の化合物。
- E及びFは、Cnアルキル及びフルオロ置換アルキル部分から選択され、nが、約3から約16の範囲である請求項11の化合物。
- 前記化合物がジシアノ置換されたものであり、I及びJは、Cnアルキル及びフルオロ置換アルキル部分から選択され、nが、約3から約16の範囲である請求項15の複合物。
- OFETデバイスに組み込まれた請求項16の複合物。
- A、D、E、H、K及びLの少なくとも1つが、シアノ置換基である請求項18の方法。
- OFETデバイスに前記化合物を組み込む請求項19の方法。
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JP2010519745A (ja) * | 2007-02-27 | 2010-06-03 | バイエル・テクノロジー・サービシズ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 表面改質剤中に囲まれた光活性半導体ナノ粒子を有するハイブリッド有機太陽電池 |
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WO2012023549A1 (ja) * | 2010-08-19 | 2012-02-23 | 住友化学株式会社 | 有機トランジスタ |
JP2014514256A (ja) * | 2011-03-03 | 2014-06-19 | ビーエーエスエフ ソシエタス・ヨーロピア | ペリレン系半導体材料 |
JP7464397B2 (ja) | 2020-01-31 | 2024-04-09 | 保土谷化学工業株式会社 | ペリレン誘導体化合物、該化合物を用いた有機半導体用組成物、該有機半導体用組成物を用いた有機薄膜トランジスタ |
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WO2005076815A2 (en) | 2005-08-25 |
EP1749316B1 (en) | 2016-06-29 |
WO2005076815A3 (en) | 2007-01-11 |
EP1749316A2 (en) | 2007-02-07 |
US20050176970A1 (en) | 2005-08-11 |
US7982039B2 (en) | 2011-07-19 |
JP4921982B2 (ja) | 2012-04-25 |
CN1980791B (zh) | 2012-08-22 |
US20100204475A1 (en) | 2010-08-12 |
KR101148868B1 (ko) | 2012-05-29 |
CA2554302C (en) | 2013-03-26 |
CN1980791A (zh) | 2007-06-13 |
KR20070014125A (ko) | 2007-01-31 |
CA2554302A1 (en) | 2005-08-25 |
US7671202B2 (en) | 2010-03-02 |
EP1749316A4 (en) | 2010-04-21 |
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