JP2015531002A - 2,7−ピレン構造単位を含むポリマー - Google Patents
2,7−ピレン構造単位を含むポリマー Download PDFInfo
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- JP2015531002A JP2015531002A JP2015518881A JP2015518881A JP2015531002A JP 2015531002 A JP2015531002 A JP 2015531002A JP 2015518881 A JP2015518881 A JP 2015518881A JP 2015518881 A JP2015518881 A JP 2015518881A JP 2015531002 A JP2015531002 A JP 2015531002A
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- 238000006116 polymerization reaction Methods 0.000 claims description 10
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- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 6
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- 150000003624 transition metals Chemical class 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
1.より広いバンドギャップを有し、その結果、より深い青色一重項発光が広い色彩空間をもつ表示用途を達成することができる材料が必要とされる。ポリマー中のより広いバンドギャップは、これらが赤色のみならず緑色三重項発光のためのホスト材料として使用することを追加的に可能とする。
R1は、出現毎に、同一であるか異なり、H、D、F、Cl、Br、I、OH、N(R2)2、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基であって、さらに、1以上のH原子は、R2で置き代えられてよく、ここで、さらに1以上の非隣接のCH2基は、O、S、Si(R2)2、Ge(R2)2、BR2、NR2、PR2、CO、C=S、C=Se、C=NR2、PO(R2)、PS(R2)、R2C=CR2、C≡C、SO、SO2、COO、O(CO)OもしくはCONR2で置き代えられてよく、またはモノあるいはポリ環式の芳香族もしくは複素環式芳香族環構造であり;
R2は、出現毎に、同一であるか異なり、H、F、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基であって、さらに、1以上のH原子は、Fで置き代えられてよく、ここで、さらに、1以上の非隣接のCH2基は、O、CO、COOもしくはO(CO)Oで置き代えられてよく、またはモノあるいはポリ環式の芳香族もしくは複素環式芳香族環構造であり;
破線は、ポリマー中の隣接する構造単位ヘの結合である。
群1:ポリマーの正孔注入および/または正孔輸送特性に作用する単位。
したがって、本発明は、素子自体と本発明によるポリマーの対応する素子での使用の両者に関する。
15g(41.7ミリモル)のジブロモピレンを250mlのジオキサン中に溶解させ、12.7g(50ミリモル)のビス(ピナコラート)ジボランと8g(81.5ミリモル)の酢酸カリウムを添加する。163mg(0.2ミリモル)の1,1-ビス(ジフェニル-ホスフィノ)フェロセンパラジウム(II)クロリド(ジクロロメタンとの錯体(1:1)、Pd 13%)をその後、添加し、バッチを110℃まで温める。TLC検査後、バッチを室温まで冷却し、200mlの水を添加する。相をその後、分離させる。有機相を水で洗浄し、水相を酢酸エチルで抽出し、合わされた有機相を次いで、硫酸マグネシウムにより乾燥させ、濾過し、溶媒を真空で揮散させる。残留物をエタノールから再結晶化させ、純度99.6%の17.2g(37.9ミリモル)(91%)の白色の固形物を生じる。
本発明によるポリマーP1〜P4と比較ポリマーV1〜V6とを、以下のモノマーを使用して、WO 03/048225 A2にしたがってスズキカップリングにより合成する(パーセントデータ=モル%)。
有機発光ダイオード(OLED)の製造は、既に文献に多数回記載されている(たとえばWO 2004/037887 A2)。例示により本発明を説明するため、表1からの本発明によるポリマーP1〜P4と比較ポリマーV1〜V6(異なる割合のモノマーを有する)をスピンコーティングにより製造する。
Claims (12)
- 一以上の式(I)の構造単位を含むポリマー。
R1は、出現毎に、同一であるか異なり、H、D、F、Cl、Br、I、OH、N(R2)2、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基であって、さらに、1以上のH原子は、R2で置き代えられてよく、ここで、さらに1以上の非隣接のCH2基は、O、S、Si(R2)2、Ge(R2)2、BR2、NR2、PR2、CO、C=S、C=Se、C=NR2、PO(R2)、PS(R2)、R2C=CR2、C≡C、SO、SO2、COO、O(CO)OもしくはCONR2で置き代えられてよく、またはモノあるいはポリ環式の芳香族もしくは複素環式芳香族環構造であり;
R2は、出現毎に、同一であるか異なり、H、F、1〜40個のC原子を有する直鎖アルキル、アルコキシもしくはチオアルコキシ基、3〜40個のC原子を有する分岐あるいは環状アルキル、アルコキシもしくはチオアルコキシ基であって、さらに、1以上のH原子は、Fで置き代えられてよく、ここで、さらに、1以上の非隣接のCH2基は、O、CO、COOもしくはO(CO)Oで置き代えられてよく、またはモノあるいはポリ環式の芳香族もしくは複素環式芳香族環構造であり;
破線は、ポリマー中の隣接する構造単位ヘの結合である。) - 1,000〜2,000,000g/molの範囲の分子量Mwを有することを特徴とする、請求項1または2記載のポリマー。
- ポリマー中の式(I)の構造単位の割合が、1〜95モル%であることを特徴とする、請求項1〜3何れか1項記載のポリマー。
- ポリマーは、また、式(I)の構造単位とは異なる少なくとも一つのさらなる構造単位を含むことを特徴とする、請求項1〜4何れか1項記載のポリマー。
- Xは、互いに独立して、同一であるか異なり、ハロゲン、O-トシレート、O-トリフレート、O-スルホネート、ボロン酸エステル、部分的にフッ素化されたシリル基、ジアゾニウム基および有機錫化合物から選ばれることを特徴とする、請求項6記載の化合物。
- 請求項1〜5何れか1項記載の少なくとも一つのポリマーと、さらに、ポリマー状、オリゴマー状、樹状および低分子量物質のクラスから選ばれる一以上の化合物を含む混合物。
- 請求項1〜5何れか1項記載の少なくとも一つのポリマーと、少なくとも一つの溶媒を含む調合物。
- 請求項1〜5何れか1項記載のポリマーまたは請求項8記載の混合物の有機電子素子での使用。
- 一以上の活性層を含む有機電子素子であって、これら活性層の少なくとも一つは、請求項1〜5何れか1項記載の一以上のポリマーまたは請求項8記載の混合物を含む、有機電子素子。
- 有機電子素子は、有機エレクトロルミネッセンス素子(OLED)、有機発光電子化学電池(OLEC)、有機集積回路(OIC)、有機電界効果トランジスタ(OFET)、有機薄膜トランジスタ(OTFT)、有機太陽電池(O-SC)、有機レーザーダイオード(O-laser)、有機光電池もしくは対応する素子(OPV)または有機光受容器(OPC)であって、好ましくは、有機エレクトロルミネッセンス素子(OLED)であることを特徴とする、請求項11記載の有機電子素子。
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PCT/EP2013/001722 WO2014000860A1 (de) | 2012-06-29 | 2013-06-12 | Polymere enthaltend 2,7-pyren-struktureinheiten |
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US11832513B2 (en) | 2017-11-23 | 2023-11-28 | Merck Patent Gmbh | Materials for electronic devices |
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US9695274B2 (en) | 2017-07-04 |
US20150322198A1 (en) | 2015-11-12 |
JP6422861B2 (ja) | 2018-11-14 |
EP2867329A1 (de) | 2015-05-06 |
WO2014000860A1 (de) | 2014-01-03 |
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