JP4404550B2 - 光学デバイスに使用すべきポリマーの調製に使用するモノマー - Google Patents
光学デバイスに使用すべきポリマーの調製に使用するモノマー Download PDFInfo
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- JP4404550B2 JP4404550B2 JP2002559423A JP2002559423A JP4404550B2 JP 4404550 B2 JP4404550 B2 JP 4404550B2 JP 2002559423 A JP2002559423 A JP 2002559423A JP 2002559423 A JP2002559423 A JP 2002559423A JP 4404550 B2 JP4404550 B2 JP 4404550B2
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- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- H10K85/115—Polyfluorene; Derivatives thereof
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Description
R=Hまたは置換基、好ましくはC1-10アルキル。
(a)上記において一般式Vで定義した第1の繰り返し単位と、ボロン酸基、ボロン酸エステル基およびボラン基から選択される少なくとも2つの反応性ボロン誘導体基とを含む第1の芳香族モノマー、並びに
(b)さらに第1の繰り返し単位及び/又は第2の繰り返し単位Ar1と、少なくとも2つの反応性ハライド官能基とを含む第2の芳香族モノマー
を重合させることを含む。
(a)上記において一般式Vで定義した第1の繰り返し単位と、1つの反応性ハライド官能基と、1つの反応性ボロン誘導体基とを含む第1の芳香族モノマー、および
(b)さらに第1の繰り返し単位及び/又は第2の繰り返し単位Ar1と、1つの反応性ハライド官能性基と、1つの反応性ボロン誘導体基とを含む第2の芳香族モノマー
を重合させることを含む。
工程1(スティル-カップリング)
この材料を実施例1(A)のペンタマー1で説明したように同様に臭素化した。
このペンタマーを例1(A)および1(B)におけるペンタマー1および2と同じ方法を使用して調製した。
収量15.2g,73.3%。1H nmr(CDCl3/TMS)8.02(2H,d);7.83(2H,s);7.23(2H,d);7.14(2H,s);6.85(2H,s);2.59(H4,t);1.90−1.28(20H);0.91(H6,t)。
収量13.4g,71.5%。1H nmr(CDCl3/TMS)7.99(2H,d,J=4.0);7.82(2H,s);7.16(2H,d,J=4.0);6.98(2H,s);2.56(H4,t,J=8.0);1.64−1.26(20H);0.91(H6,t,J=8.0)。
ポリマーの調製
本発明によるポリマーを、WO00/53656の方法に従い、分子量を制限するために10mol%のブロモチオフェンの存在下において、トルエン(40mL)中で9,9−ジ−n−オクチルフルオレン−2,7−ジエチレンボロネート(1.9132g,3.6mmol)と、ペンタマー1(2.8526g,3.6mmol)とを反応させることによって調製した。
エレクトロルミネセンスデバイス
適切なデバイス構造を図1に示す。アノード2はガラスまたはプラスチック基板上に支持された透明なインジウム-スズ酸化物(“ITO”)の層である。アノード2の層は、1000−2000Åの厚さをもち、一般的にはおよそ1500Åである。カソード5はおよそ1500Åの厚さをもつCa層である。電極の間には、およそ1000Åの厚さをもつ発光層4がある。発光層4は本ポリマーを0.5ないし30重量%含み、発光層の残りは正孔及び/又は電子輸送材料及び/又は発光材料からなる。好ましくは、デバイスはおよそ1000Åの厚さをもつPEDOTの正孔輸送材料層3を含む。層6は適切な厚さの封止層である。
光起電力の応用
光起電力デバイスの効果的な形態は、ポリ(3−ヘキシルチオフェン)(P3HT)といった電子供与体と、F8-トリマーのコポリマー(下記)といった電子受容体とのブレンドを活性材料として含むものである。ブレンドを含む光起電力デバイスはUS567,0791に開示されている。
PLEDの応用
図3に示したフォトルミネセンススペクトルからわかるように、F8−ペンタマー1のコポリマーのルミネセンスは、F8-トリマーのコポリマーと比較してレッドシフトしている。
Claims (32)
- 各々のArは同一である請求項1ないし4のいずれか1つに記載のモノマー。
- 少なくとも1つのArは少なくとも1つのC1-10アルキルまたはC1-10アルコキシ置換基を含む、請求項1ないし5のいずれか1つに記載のモノマー。
- 前記反応性ハライド官能基は、F、Cl、BrまたはIからなる群から選択され、前記反応性ボロン誘導体基は、ボロン酸基、ボロン酸エステル基またはボラン基からなる群から選択される、請求項1ないし6のいずれか1つに記載のモノマー。
- 請求項1ないし7のいずれか1つに定義したモノマーから調製されたポリマー。
- さらに、置換または非置換のアリールまたはヘテロアリール基である第2の繰り返し単位Ar1を含む請求項8または9に記載のポリマー。
- さらに、置換または非置換のアリールまたはヘテロアリール基である第3の繰り返し単位Ar2を含む請求項10に記載のポリマー。
- Ar1およびAr2の少なくとも1つは、置換もしくは非置換のフルオレン基または置換もしくは非置換のベンゾチアジアゾール基を含む請求項10または請求項11に記載のポリマー。
- ポリマーは0.1mol%ないし50mol%の第1の繰り返し単位を含む請求項9ないし13のいずれか1つに記載のポリマー。
- 550nmないし1000nmの波長域で発光することができる請求項8ないし14のいずれか1つに記載のポリマー。
- ポリマー主鎖は完全に共役している請求項8ないし15のいずれか1つに記載のポリマー。
- 光学デバイスにおける成分としての請求項8ないし16のいずれか1つに定義したポリマーの使用方法。
- 前記光学デバイスは、エレクトロルミネセンスデバイスまたは光起電力デバイスを含む請求項17に記載のポリマーの使用方法。
- 請求項8ないし16のいずれか1つに定義したポリマーを含むフィルム。
- 請求項8ないし16のいずれか1つに定義したポリマーを含むコーティング。
- 請求項8ないし16のいずれか1つに定義したポリマーを含む混合物を含む組成物。
- 前記混合物は、1つまたは2つのさらなる異なるポリマーを含む請求項21に記載の組成物。
- 反応混合物中において、
(a)一般式Iにおいて、EおよびE’がボロン酸基、ボロン酸エステル基、およびボラン基から選択された少なくとも2つの反応性ボロン誘導体基である第1の芳香族モノマー、並びに、
(b)さらに、一般式Iにおいて、EおよびE’が反応性ハライド官能基であるモノマー、及び/又はその両端に少なくとも2つの反応性ハライド官能基を含む、置換または非置換のアリールまたはヘテロアリール基であるAr1を含む、第2の芳香族モノマー
を重合させる工程を含み、
前記反応混合物は、芳香族モノマーの重合を触媒するのに適切な触媒量の触媒と、反応性ボロン誘導官能基を−BX3 −アニオン基(ここでXは独立してF、アルコキシおよびOHからなる群から選択される)に変換するのに十分な量の有機塩基とを含み、一般式Iは、
ポリマーを作製する方法。 - 反応混合物中において、
(a)一般式Iにおいて、EおよびE’が一方が1つの反応性ハライド官能基であり、他方がボロン酸基、ボロン酸エステル基およびボラン基から選択された1つの反応性ボロン誘導体基である第1の芳香族モノマー、並びに、
(b)さらに、一般式Iにおいて、EおよびE’が一方がボロン酸基、ボロン酸エステル基およびボラン基から選択された反応性ボロン誘導体基であって、他方が反応性ハライド官能基であるモノマー、及び/又はその両端に1つのボロン酸基、ボロン酸エステル基およびボラン基から選択された反応性ボロン誘導体基と、反応性ハライド官能基とを含む、置換または非置換のアリールまたはヘテロアリール基であるAr1を含む、第2の芳香族モノマー
を重合させる工程を含み、
前記反応混合物は、芳香族モノマーの重合を触媒するのに適切な触媒量の触媒と、反応性ボロン誘導体官能基を−BX3 -アニオン基(ここでXは独立してF、アルコキシおよびOHからなる群から選択される)に変換するのに十分な量の有機塩基とを含み、一般式Iは、
ポリマーを作製する方法。 - 基板と、基板上に支持された請求項8ないし16のいずれか1つに記載のポリマーとを含む光学デバイス。
- 前記光学デバイスは、エレクトロルミネセンスデバイスを含む請求項26に記載の光学デバイス。
- 前記エレクトロルミネセンスデバイスは、
正電荷キャリアを注入する第1の電荷注入層と、
負電荷キャリアを注入する第2の電荷注入層と、
第1と第2の電荷注入層の間に位置して正および負電荷キャリアを受け入れ結合させて発光させる、請求項8ないし16のいずれか1つに定義したポリマーを含む発光材料を含む発光層と
を具備する請求項27に記載の光学デバイス。 - 前記光学デバイスは、光電子デバイスまたは光起電力デバイスを含む請求項26に記載の光学デバイス。
- ポリマーを調製するための請求項1ないし7のいずれか1つに定義されたモノマーの使用方法。
- ポリマーを光学デバイスの成分として提供する請求項30に記載のモノマーの使用方法。
- ポリマーを光学デバイスの発光成分として提供する請求項31に記載のモノマーの使用方法。
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GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
GB9018698D0 (en) | 1990-08-24 | 1990-10-10 | Lynxvale Ltd | Semiconductive copolymers for use in electroluminescent devices |
US6242561B1 (en) * | 1996-03-06 | 2001-06-05 | Basf Aktiengesellschaft | Substituted polythiophenes, processes for their preparation their use |
US6309763B1 (en) * | 1997-05-21 | 2001-10-30 | The Dow Chemical Company | Fluorene-containing polymers and electroluminescent devices therefrom |
US5777070A (en) | 1997-10-23 | 1998-07-07 | The Dow Chemical Company | Process for preparing conjugated polymers |
GB9805476D0 (en) | 1998-03-13 | 1998-05-13 | Cambridge Display Tech Ltd | Electroluminescent devices |
KR100697861B1 (ko) * | 1998-03-13 | 2007-03-22 | 캠브리지 디스플레이 테크놀로지 리미티드 | 전장 발광 디바이스들 |
JP4505146B2 (ja) | 1999-02-04 | 2010-07-21 | ダウ グローバル テクノロジーズ インコーポレイティド | フルオレンコポリマーおよびそれから作られる素子 |
EP1165648B1 (en) | 1999-03-05 | 2007-08-15 | Cambridge Display Technology Limited | Polymer preparation |
US20030186079A1 (en) | 2000-01-05 | 2003-10-02 | Carl Towns | Luminescent polymer |
GB0004541D0 (en) | 2000-02-25 | 2000-04-19 | Cambridge Display Tech Ltd | Luminescent polymer |
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ATE342900T1 (de) | 2006-11-15 |
CN1487937A (zh) | 2004-04-07 |
DE60215464D1 (de) | 2006-11-30 |
US7534503B2 (en) | 2009-05-19 |
EP1366046A1 (en) | 2003-12-03 |
WO2002059121A1 (en) | 2002-08-01 |
DE60215464T2 (de) | 2007-04-19 |
CN1263754C (zh) | 2006-07-12 |
US20040115473A1 (en) | 2004-06-17 |
HK1061019A1 (en) | 2004-09-03 |
EP1366046B1 (en) | 2006-10-18 |
JP2004534863A (ja) | 2004-11-18 |
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