JP5836935B2 - 共役ポリマーおよび有機半導体としてのそれらの使用 - Google Patents
共役ポリマーおよび有機半導体としてのそれらの使用 Download PDFInfo
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- JP5836935B2 JP5836935B2 JP2012512228A JP2012512228A JP5836935B2 JP 5836935 B2 JP5836935 B2 JP 5836935B2 JP 2012512228 A JP2012512228 A JP 2012512228A JP 2012512228 A JP2012512228 A JP 2012512228A JP 5836935 B2 JP5836935 B2 JP 5836935B2
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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- H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
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- H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
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- H05B33/00—Electroluminescent light sources
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- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H10K10/40—Organic transistors
- H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
- H10K10/462—Insulated gate field-effect transistors [IGFETs]
- H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
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- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Thin Film Transistor (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
R1は、それぞれの出現において同一または異なって、H、直鎖状、分岐状または環状で1〜40個のC原子を有するアルキル基(該基は無置換であるか、1個以上の基Rで置換されており、ただし、1個以上のC原子は、O−および/またはS−原子がそれぞれ互いに直接連結しないようにして、O、S、CO、CO−O、O−CO、O−CO−O、CR=CRまたはC≡Cで置き換えられていてもよく、好ましくは、ヘテロ原子は式Iにおけるフェナントレン単位に直接結合しておらず、ただし、1個以上のH原子は、F、Cl、Br、IまたはCNで置き換えられていてもよい。)を表すか、または、R1は、2〜40個のC原子を有するアリールまたはヘテロアリール基(該基は無置換であるか、1個以上の基Rで置換されている。)または複数のこれらの基の組み合わせを表し;ただし、また、2個の基R1は、互いに単環状または多環状の脂肪族基を更に形成していてもよく、
R2、3は、それぞれ互いに独立に、R1に与えられる意味の1つを有し、
X、Yは、それぞれの出現において同一または異なって、それぞれ互いに独立に、CR=CR、C≡C、2〜40個のC原子を有する2価のアリールまたはヘテロアリール基(該基は無置換であるか、1個以上の基R1で置換されている。)を表し、
Rは、それぞれの出現において同一または異なって、H、直鎖状、分岐状または環状で1〜22個のC原子を有するアルキルまたはアルコキシ基(ただし、1個以上のC原子は、O−および/またはS−原子がそれぞれ互いに直接連結しないようにして、O、S、CO、CO−O、O−CO、O−CO−O、CR0=CR0、C≡Cで置き換えられていてもよく、ただし、1個以上のH原子は、F、Cl、Br、IまたはCNで置き換えられていてもよい。)であるか、または、Rは、5〜40個のC原子を有するアリール、ヘテロアリール、アリールオキシまたはヘテロアリールオキシ基(該基は無置換であるか、1個以上の非芳香族基R0で置換されている。)であり;また、2個以上の基Rは、互いにおよび/またはR0と共に環系を形成していてもよく;または、Rは、F、Cl、Br、I、CN、Sn(R0)3、Si(R0)3またはB(R0)2であり、
R0は、それぞれの出現において同一または異なって、Hまたは1〜20個のC原子を有する脂肪族または芳香族炭化水素基であり;また、2個の基R0は、それらが連結されているヘテロ原子(Sn、SiまたはB)と共に環を形成していてもよく、
a、bは、それぞれの出現において同一または異なって、それぞれ互いに独立に、0、1または2を表す。
−ソース電極と、
−ドレイン電極と、
−ゲート電極と、
−有機半導体(OSC:organic semiconducting)層と、
−1つ以上ゲート絶縁体層と、
−任意構成として基板と、
を含み、
ただし、OSC層は、本発明による1種類以上のポリマーを含む。
−低仕事関数電極(例えば、アルミニウム)と、
−一方は透明である高仕事関数電極(例えば、ITO)と、
−ホール輸送および電子輸送材料から成る二重層と;ただし、該二重層は、2つの別個の層として、または、ブレンドされた混合物、所謂、バルクヘテロ接合(BHJ:bulk heterojunction)としてのいずれで存在してもよく(例えば、Coakley、K.M.およびMcGehee、M.D.Chem.Mater.2004年、16巻、4533頁を参照)、
−任意の構成要素として、ホールに対するオーミックコンタクトを与えるために高仕事関数電極の仕事関数を改変するための導電性ポリマー層(例えば、PEDOT:PSSなど)と、
−任意の構成要素として、電子に対するオーミックコンタクトを与えるための高仕事関数電極上のコーティング(LiFなど)と
を含む。
以下に記載される通りの手順(これは、また、国際特許出願公開第03/048225号パンフレットにも開示されている。)によって、下に示される通りのモノマー(1)および(2)より共役交互コポリマーP1を調製する。
例1に記載される方法に類似して、下に示される通りのモノマー(3)および(4)(それぞれ50mol%)より共役交互コポリマーP2を調製する。
例1に記載される方法に類似して、例2のモノマー(3)と、下に示される通りのモノマー(5)と(それぞれ50mol%)より共役交互コポリマーP3を調製する。
以下に記載される通りの手順によって、例1のモノマー(1)および(2)と、下に示される通りのモノマー(7)とより共役ポリマーC2を調製する。
比較例1に記載される通りの手順によって、例1のモノマー(2)と、下に示される通りのモノマー(8)と(それぞれ50mol%)より共役ポリマーC3を調製する。
トップゲートトランジスタ装置を以下の通り調製する:
高品質トランジスタ品位のガラスを3%デコン中において70℃で30分浄化する。トランジスタ品位は、特に、イオン性の不純物が低く、可能な限り平滑な表面を有するように設計されている。次いで、水を少なくとも5回交換して水中でガラスをリンスし、表面に浄化剤が残存していないことを確実にする。次いで、基板をエアーガンで乾燥する。この清浄な表面に対して、対応するチャネル長の装置に、10、20、50μmのギャップを有するシャドーマスクを通して、銀製のソースドレイン電極を、ほぼ30nmに熱蒸着する。銀の堆積直後に、自己組織化単分子膜(SAM:self assembled monolayer)処理を使用して、ポリマーへのコンタクトがオーム性となるように、電極の仕事関数を好ましい状態に改変する。基板をSAM処理(これは、IPA中のペンタフルオロベンゼンチオール(5mM)である。)に30秒浸漬し、次いでIPAでリンスする。空気からの混入物の望ましくない増大を避けるために、蒸着後、可能な限り早急にSAM処理を行わなければならない。次いで、500において3秒、次いで2000rpmにおいて30秒で、トルエン(5mg/ml)より有機半導体(OSC:organic semiconductor)をスピンコートし、次いで、ホットプレート上で100℃において1分アニールする。基板が冷却され次第、基板上に低K誘電体をスピンコート(目標1μm)し、100℃で1分アニールし、最後に、約30nmの厚みまでゲート電極を熱堆積する。
Claims (15)
- 式IIIaの構造を有する共役ポリマー。
Aは式Iの繰り返し単位であり、
Bは式IIの繰り返し単位であり、
nは1より大きい整数であり、
ただし、AおよびBは、アミンまたはイミン基を含有せず、
R1は、それぞれの出現において同一または異なって、H、直鎖状、分岐状または環状で1〜40個のC原子を有するアルキル基(該基は無置換であるか、1個以上の基Rで置換されており、ただし、1個以上のC原子は、O−および/またはS−原子がそれぞれ互いに直接連結しないようにして、O、S、CO、CO−O、O−CO、O−CO−O、CR=CRまたはC≡Cで置き換えられていてもよく、ただし、1個以上のH原子は、F、Cl、Br、IまたはCNで置き換えられていてもよい。)を表すか、または、R1は、2〜40個のC原子を有するアリールまたはヘテロアリール基(該基は無置換であるか、1個以上の基Rで置換されている。)または複数のこれらの基の組み合わせを表し;ただし、また、2個の基R1は、互いに単環状または多環状の脂肪族基を更に形成していてもよく、
R2、3は、それぞれ互いに独立に、R1に与えられる意味の1つを有し、
X、Yは、それぞれの出現において同一または異なって、それぞれ互いに独立に、CR=CR、C≡C、2〜40個のC原子を有する2価のアリールまたはヘテロアリール基(該基は無置換であるか、1個以上の基R1で置換されている。)を表し、
Rは、それぞれの出現において同一または異なって、H、直鎖状、分岐状または環状で1〜22個のC原子を有するアルキルまたはアルコキシ基(ただし、1個以上のC原子は、O−および/またはS−原子がそれぞれ互いに直接連結しないようにして、O、S、CO、CO−O、O−CO、O−CO−O、CR0=CR0、C≡Cで置き換えられていてもよく、ただし、1個以上のH原子は、F、Cl、Br、IまたはCNで置き換えられていてもよい。)であるか、または、Rは、5〜40個のC原子を有するアリール、ヘテロアリール、アリールオキシまたはヘテロアリールオキシ基(該基は無置換であるか、1個以上の非芳香族基R0で置換されている。)であり;また、2個以上の基Rは、互いにおよび/またはR0と共に環系を形成していてもよく;または、Rは、F、Cl、Br、I、CN、Sn(R0)3、Si(R0)3またはB(R0)2であり、
R0は、それぞれの出現において同一または異なって、Hまたは1〜20個のC原子を有する脂肪族または芳香族炭化水素基であり;また、2個の基R0は、それらが連結されているヘテロ原子と共に環を形成していてもよく、
a、bは、それぞれの出現において同一または異なって、それぞれ互いに独立に、0、1または2を表す。) - 式IIIaの構造を有する共役ポリマー。
Aは、サブ式Ia〜Icより選択される繰り返し単位であり、
Bは、サブ式II1〜II3より選択される繰り返し単位であり、
nは1より大きい整数であり、
ただし、AおよびBは、アミンまたはイミン基を含有せず、
R1は、それぞれの出現において同一または異なって、H、直鎖状、分岐状または環状で1〜40個のC原子を有するアルキル基(該基は無置換であるか、1個以上の基Rで置換されており、ただし、1個以上のC原子は、O−および/またはS−原子がそれぞれ互いに直接連結しないようにして、O、S、CO、CO−O、O−CO、O−CO−O、CR=CRまたはC≡Cで置き換えられていてもよく、ただし、1個以上のH原子は、F、Cl、Br、IまたはCNで置き換えられていてもよい。)を表すか、または、R1は、2〜40個のC原子を有するアリールまたはヘテロアリール基(該基は無置換であるか、1個以上の基Rで置換されている。)または複数のこれらの基の組み合わせを表し;ただし、また、2個の基R1は、互いに単環状または多環状の脂肪族基を更に形成していてもよく、
Yは、それぞれの出現において同一または異なって、それぞれ互いに独立に、CR=CR、C≡C、2〜40個のC原子を有する2価のアリールまたはヘテロアリール基(該基は無置換であるか、1個以上の基R1で置換されている。)を表し、
Rは、それぞれの出現において同一または異なって、H、直鎖状、分岐状または環状で1〜22個のC原子を有するアルキルまたはアルコキシ基(ただし、1個以上のC原子は、O−および/またはS−原子がそれぞれ互いに直接連結しないようにして、O、S、CO、CO−O、O−CO、O−CO−O、CR0=CR0、C≡Cで置き換えられていてもよく、ただし、1個以上のH原子は、F、Cl、Br、IまたはCNで置き換えられていてもよい。)であるか、または、Rは、5〜40個のC原子を有するアリール、ヘテロアリール、アリールオキシまたはヘテロアリールオキシ基(該基は無置換であるか、1個以上の非芳香族基R0で置換されている。)であり;また、2個以上の基Rは、互いにおよび/またはR0と共に環系を形成していてもよく;または、Rは、F、Cl、Br、I、CN、Sn(R0)3、Si(R0)3またはB(R0)2であり、
R0は、それぞれの出現において同一または異なって、Hまたは1〜20個のC原子を有する脂肪族または芳香族炭化水素基であり;また、2個の基R0は、それらが連結されているヘテロ原子と共に環を形成していてもよく、
ただし、「alkyl」および「aryl」は、サブ式Ia〜Icで定義される基Rで置換されていてもよい。) - ヘテロ原子は式Iにおけるフェナントレン単位に直接結合していないことを特徴とする請求項1〜4のいずれか1項に記載のポリマー。
- (1)出現する全てのR 1 は、同時にはHを表さず、
(2)出現する全てのR 2 は、同時にはHを表さず、および
(3)出現する全てのR 3 は、同時にはHを表さない
ことを特徴とする請求項1〜5のいずれか1項に記載のポリマー。 - 請求項1〜8のいずれか1項に記載の1種類以上のポリマーと、1種類以上の他のポリマーとを含むポリマーブレンド。
- 他のポリマーは、半導体性、電荷輸送、ホール/電子輸送、ホール/電子ブロック、導電性、光導電性または発光特性を有するポリマーより選択されることを特徴とする請求項9に記載のポリマーブレンド。
- 請求項1〜8のいずれか1項に記載の1種類以上のポリマーまたは請求項9または10に記載のポリマーブレンドと、1種類以上の有機溶媒とを含む配合物。
- 光学的、電気光学的、電子的、エレクトロルミネセントまたはフォトルミネセント部品または装置における、電荷輸送、半導体、導電性、光導電性または発光材料としての、請求項1〜11のいずれか1項に記載のポリマー、ポリマーブレンドまたは配合物の使用。
- 請求項1〜11のいずれか1項に記載のポリマー、ポリマーブレンドまたは配合物を含む光学的、電気光学的または電子的部品または装置。
- 有機電界効果トランジスタ(OFET:organic field effect transistor)、薄膜トランジスタ(TFT:thin film transistor)、集積回路(IC:integrated circuit)、論理回路、キャパシタ、無線識別(RFID:radio frequency identification)タグ、装置または部品、有機発光ダイオード(OLED:organic light emitting diode)、有機発光トランジスタ(OLET:organic light emitting transistor)、フラットパネルディスプレイ、ディスプレイのバックライト、有機光起電(OPV:organic photovoltaic)装置、ソーラーセル、レーザーダイオード、光導電体、光検出器、電子写真装置、電子写真記録装置、有機記憶装置、センサー装置、ポリマー発光ダイオード(PLED:polymer light emitting diode)における電荷注入層、電荷輸送層または中間層、ショットキーダイオード、平坦化層、帯電防止フィルム、ポリマー電解質膜(PEM:polymer electrolyte membrane)、導電性基板、導電性パターン、電池における電極材料、配向層、バイオセンサー、バイオチップ、セキュリティーマーク、セキュリティー装置、および、DNA配列を検出および区別するための部品または装置から成る群より選択される請求項13に記載の部品または装置。
- 式IVの1種類以上のモノマーと、式Vの1種類以上のモノマーとをアリール−アリールカップリング反応させることによって、請求項1〜8のいずれか1項に記載のポリマーを調製する方法。
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GB2453457B (en) * | 2006-05-12 | 2011-06-01 | Merck Patent Gmbh | Indenofluorene polymer based organic semiconductor materials |
DE102006022670A1 (de) | 2006-05-16 | 2007-11-22 | Continental Aktiengesellschaft | Fahrzeugluftreifen |
EP2044139B1 (en) | 2006-07-21 | 2011-12-21 | Merck Patent GmbH | Copolymers of indenofluorene and thiophene |
EP2344928A1 (en) * | 2008-09-09 | 2011-07-20 | Merck Patent GmbH | Organic material and electrophotographic device |
US20110180791A1 (en) * | 2008-09-09 | 2011-07-28 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Copolymer for electronic devices |
DE102008049037A1 (de) * | 2008-09-25 | 2010-04-22 | Merck Patent Gmbh | Neue Polymere mit niedriger Polydispersität |
-
2010
- 2010-05-04 WO PCT/EP2010/002695 patent/WO2010136112A1/en active Application Filing
- 2010-05-04 KR KR1020117031396A patent/KR101854920B1/ko active IP Right Grant
- 2010-05-04 US US13/322,625 patent/US8398895B2/en active Active
- 2010-05-04 JP JP2012512228A patent/JP5836935B2/ja not_active Expired - Fee Related
- 2010-05-04 EP EP10718085A patent/EP2435496A1/en not_active Withdrawn
- 2010-05-04 CN CN201080022854.XA patent/CN102449022B/zh not_active Expired - Fee Related
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KR101854920B1 (ko) | 2018-05-04 |
EP2435496A1 (en) | 2012-04-04 |
US20120068121A1 (en) | 2012-03-22 |
US8398895B2 (en) | 2013-03-19 |
TW201105702A (en) | 2011-02-16 |
JP2012528210A (ja) | 2012-11-12 |
KR20120036898A (ko) | 2012-04-18 |
CN102449022B (zh) | 2015-06-24 |
WO2010136112A1 (en) | 2010-12-02 |
WO2010136112A8 (en) | 2011-08-04 |
CN102449022A (zh) | 2012-05-09 |
TWI500652B (zh) | 2015-09-21 |
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