JP4050988B2 - 置換フルオレンポリマー、その製造方法、及びこれを用いた光学装置 - Google Patents
置換フルオレンポリマー、その製造方法、及びこれを用いた光学装置 Download PDFInfo
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- 0 *c1cc(BrCCCO)ccc1-c(cc1)ccc1Br Chemical compound *c1cc(BrCCCO)ccc1-c(cc1)ccc1Br 0.000 description 1
- CWGRCRZFJOXQFV-UHFFFAOYSA-N O=C(c1c2)c3cc(Br)ccc3-c1ccc2Br Chemical compound O=C(c1c2)c3cc(Br)ccc3-c1ccc2Br CWGRCRZFJOXQFV-UHFFFAOYSA-N 0.000 description 1
- QHWXUVMQYLVAIY-UHFFFAOYSA-N OC(c1cc(Br)ccc1-c(cc1)ccc1Br)([AlH2])[AlH2] Chemical compound OC(c1cc(Br)ccc1-c(cc1)ccc1Br)([AlH2])[AlH2] QHWXUVMQYLVAIY-UHFFFAOYSA-N 0.000 description 1
- GPFSKIMMYYLPPH-UHFFFAOYSA-N OC(c1cc(Br)ccc1-c(cc1)ccc1Br)=O Chemical compound OC(c1cc(Br)ccc1-c(cc1)ccc1Br)=O GPFSKIMMYYLPPH-UHFFFAOYSA-N 0.000 description 1
- WOOPLYNZHIKJTB-UHFFFAOYSA-N [AlH2]C1(c2cc(Br)ccc2-c(cc2)c1cc2Br)[AlH2] Chemical compound [AlH2]C1(c2cc(Br)ccc2-c(cc2)c1cc2Br)[AlH2] WOOPLYNZHIKJTB-UHFFFAOYSA-N 0.000 description 1
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Description
WO00/55927は次式(a)を有するポリマーを開示している。
この出願は、ジフェニルフルオレン繰返し単位からなるポリマーを開示していない。
WO00/22026は次式(b)を有するポリマーを開示している。
ジフェニルフルオレン繰り返し単位からなる冷光放射性ポリマーの他の開示は、次のものがある。
前記ポリマーは、選択的に置換される次式(I)の繰返し単位を有する。
好ましくは、各Arは次式(II)を有する選択的に置換される残部からなる群から独立して選択される。
第3の側面において、本発明は、次式(III)のモノマー混合物の重合を含むポリマーのガラス転移温度の制御方法を提供する。
好ましくは、塩基は有機塩基であり、より好ましくは、WO00/53656に開示されるようにテトラ−アルキルアンモニウムカルボネート又はハイドロオキサイドである。
上記で定義された「正孔輸送領域」、「電子輸送領域」及び「発光領域」の用語は、下記の概要に示されるように互いに相対的に定義される。
典型的な冷光放射性装置は、4.8eVの仕事関数を有するアノードを有する。したがって、正孔輸送領域のHOMOレベルは、好ましくは約4.8−5.5eVである。同様に、典型的な装置のカソードは、約3eVの仕事関数を有するであろう。したがって、電子輸送領域のLUMOレベルは、好ましくは約3−3.5eVである。
式(I)の繰返し単位及びこれらの共役鎖は、電子輸送領域としてだけでなく本発明のガラス転移温度の増加をはかる機能としても働く。さらに電子輸送領域として好ましい材料は、1,4結合フェニル繰返し単位及びこれらの共役された鎖である。
発光領域として好ましい材料は、WO00/55927及びWO00/46321に開示される発光繰返し単位である。特に好ましい青色発光繰返し単位は、選択的に置換された次式(IV)の繰返し単位を有する。
1H NMR (CDCl3) 7.73 (2H, d, J 2.0), 7.61 (2H, dd, J 7.6, 2.0), 7.36 (2H, d, J 8.0); 13C NMR (CDCl3) 142.3, 137.5, 135.3, 127.9, 123.3, 121.8, 109.8。
1H NMR ((CD3)2CO) 8.00 (1H, d, J 2.0), 7.77 (1H, dd, J 8.0, 2.4), 7.57 (2H, d, J 8.0), 7.34 (1H, d, J 8.4), 7.29 (2H, d, J 8.8) ; 13C NMR ((CD3)2CO) 167.1, 140.4, 139.8, 134.2, 133.5, 132.8, 132.7, 131.2, 130.6, 121.4, 121.1。
4,4−ジブロモ−2−カルボン酸ビフェニル(171.14g,0.481mol)がメタノール(700ml)及び硫酸(15ml)中に浮遊させ、80℃で21時間過熱した。溶媒は除去され、油はエチルアセテート中に溶解した。この溶媒は2Nの水酸化ナトリウム、水、飽和塩化ナトリウムで洗浄され、硫酸マグネシウム上で乾燥され、ろ過され、蒸発してオレンジ色の油が得られた。この油は、熱いメタノールで処理され、エステルを冷却して、沈殿化させろ過した。母液は蒸発され、固体は再結晶化されて追加の生成物が得られた。エステルはGCMSにより100%純化され、123.27g(69%)の生成物が得られた。
1H NMR (CDCl3) 7.99 (1H, d, J 2.0), 7.64 (1H, dd, J 8.0, 1.6), 7.51 (2H, d, J 8.4), 7.19 (1H, d, J 8.8), 7.13 (2H, d, J 8.8) , 3.67 (3H, s) ; 13C NMR (CDCl3) 167.1, 140.3, 139.1, 134.4, 132.9, 132.1, 132.0, 131.3, 129.8, 121.9, 121.5, 52.3; GCMS: M+ = 370。
GC-MS (m/z, relative intensity %) 494 (M+, 100);1H NMR (CDCl3) 7.43 (1H, dd, J 8.4, 2.4), 7.28 (6H, m), 7.23 (2H, d, J 8.0), 7.11 (4H, m), 6.99 (1H, d, J 2.4), 6.94 (1H, d, J 8.4), 6.61 (2H, d, J 8.4) ; 13C NMR (CDCl3) 147.5, 146.7, 140.3, 139.3, 134.0, 133.0, 131.2, 131.1, 130.3, 128.2, 128.1, 127.8, 121.8, 121.3, 83.2。
1H NMR (CDCl3), δ/ppm: 7.58 (2H, d, J 7.6), 7.49 (2H, d, 1.2), 7.48 (2H, dd, 1.6), 7.25 (6H, m), 7.14 (4H, m).
13C NMR (CDCl3), δ/ppm: 153.2, 144.6, 138.3, 131.1, 129.6, 128.7, 128.2, 127.4, 122.0, 121.7, 65.8。
下記の表に記載されるAr基を有するモノマーが、上記で概略記載したスキーム及び一般的実験プロセスにしたがって製造された。表に示されるAr基に対応するアリールリチウム化合物は対応するアリール臭化物から製造された。
本発明の青色電子冷光放射性ポリマーが、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)(0.5価)、2,7−ジブロモ−9,9−ジフェニルフルオレン−2,7−ジ(エチレニルボロネート)(0.5価)、2,7−ジブロモ−9,9−ジフェニルフルオレン(0.3価)、N,N−ジ(4−ブロモフェニル)−セク−ブチルフェニルアミン(0.1価)及びN,N’−ジ(4−ブロモフェニル)−N,N’−ジ(4−n−ブチルフェニル)−1,4−ジアミノベンゼン(0.1価)の反応によるWO00/53656のプロセスにしたがって製造された。
ポリマーにおける9,9−ジオクチルフルオレン繰返し単位及び9,9−ジフェニルフルオレン繰返し単位の割合が下記のように変動する点を除いて、ポリマーが実施例P1の方法に従って製造された。
2,7−ジブロモ−9,9−ジ(ビフェニル)フルオレン(モノマー実施例M3;0.3価)が2,7−ジブロモ−9,9−ジフェニルフルオレンに代えて使用される点を除いて、実施例P1の方法にしたがってポリマーが製造された。
WO00/55927に開示されるように、実施例1のポリマーにしたがって青色発光ポリマーが製造された。ここで、全ての9,9−ジフェニルフルオレン繰返し単位が9,9−ジ−n−オクチルフルオレン繰返し単位に代えられた。これは、2,7−ジブロモ−9,9−ジフェニルフルオレンに代えて2,7−ジブロモ−9,9−ジ−n−オクチルフルオレンの0.3かが使用されるポリマーの実施例1の製造方法に従って行われた。
ガラス基板上の一定の厚さのITO基板に、ポリ(エチレンジオキシチオフェン)/ポリスチレンサルファネート(BaytronPTMからBayerTMとして有効な)が270ミクロンの厚さまでスピンコーティングにより導入された。この上に、本発明のポリマーがスピンコーティングにより厚さ50nmまで積層された。リチウムフルオライド(厚さ4nm)の層が、ポリマー上に気相蒸着し、その上にカルシウムのカソード(厚さ50nm)が再度気相蒸着された。装置は、金属缶を用いてカプセル化された。
上記の比較例のポリマーを本発明のポリマーに代える以外は上記装置の実施例の製造概要に沿って、装置が製造された。
結果
上記のポリマーのガラス転移温度が下記の表に示される。
本発明は特定の模範的な実施例によって説明できるが、特許請求の範囲で規定する発明の思想及び範囲を超えない限り、本明細書で開示する特徴の多様な変形、代替及び/又は組合せは当業者にとって明らかであると言えるだろう。
2 カソード
3 電子冷光放射材料
4 アノード
Claims (9)
- Rがブチルである請求項1に記載のポリマー。
- 請求項1に記載される式(I)の繰返し単位を50mol%以下含有する請求項1又は2に記載のポリマー。
- 請求項1に記載される式(I)の繰返し単位を10〜40mol%含有する請求項3に記載のポリマー。
- 電子輸送領域が少なくとも1つの請求項1に記載される式(I)の繰返し単位を有する請求項1ないし4のいずれかに記載のポリマー。
- 電子輸送領域が請求項1に記載される式(I)の繰返し単位(I)を有しない請求項1ないし4のいずれかに記載のポリマー。
- 波長の範囲が400〜500nmである光を放射することができる請求項1ないし6のいずれかに記載のポリマー。
- 好ましくは430〜500nmである光を放射することができる請求項1ないし6のいずれかに記載のポリマー。
- 正電荷注入のための第1電極、負電荷注入のための第2電極、並びに請求項1ないし8のいずれかに記載されるポリマーを含み第1電極と第2電極の間に位置する層からなる電子冷光放射性装置。
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GBGB0111549.2A GB0111549D0 (en) | 2001-05-11 | 2001-05-11 | Polymers, their preparation and uses |
US31562301P | 2001-08-29 | 2001-08-29 | |
PCT/GB2002/002167 WO2002092723A1 (en) | 2001-05-11 | 2002-05-10 | Substituted fluorene polymers, their preparation and use in optical devices |
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JP2006296171A Division JP5048995B2 (ja) | 2001-05-11 | 2006-10-31 | ポリマーのガラス転移温度制御方法及びこれを用いたポリマー |
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CN (2) | CN100417703C (ja) |
AT (2) | ATE292662T1 (ja) |
DE (2) | DE60203610T2 (ja) |
GB (1) | GB0111549D0 (ja) |
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GB0111549D0 (en) * | 2001-05-11 | 2001-07-04 | Cambridge Display Tech Ltd | Polymers, their preparation and uses |
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2001
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Cited By (1)
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JP2009024174A (ja) * | 2001-05-11 | 2009-02-05 | Cambridge Display Technol Ltd | 置換フルオレンポリマー及びその製造方法 |
Also Published As
Publication number | Publication date |
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EP1586617A1 (en) | 2005-10-19 |
GB0111549D0 (en) | 2001-07-04 |
DE60203610T2 (de) | 2005-09-15 |
CN1513044A (zh) | 2004-07-14 |
ATE273363T1 (de) | 2004-08-15 |
DE60200951D1 (de) | 2004-09-16 |
WO2002092723A1 (en) | 2002-11-21 |
TWI279429B (en) | 2007-04-21 |
DE60200951T2 (de) | 2005-01-27 |
EP1385918B1 (en) | 2005-04-06 |
EP1385918A1 (en) | 2004-02-04 |
TWI304436B (en) | 2008-12-21 |
CN101215370A (zh) | 2008-07-09 |
ATE292662T1 (de) | 2005-04-15 |
JP4959100B2 (ja) | 2012-06-20 |
DE60203610D1 (de) | 2005-05-12 |
WO2002092724A1 (en) | 2002-11-21 |
EP1385919B1 (en) | 2004-08-11 |
CN100417703C (zh) | 2008-09-10 |
JP2004527628A (ja) | 2004-09-09 |
CN101215370B (zh) | 2012-06-20 |
EP1385919A1 (en) | 2004-02-04 |
JP2004532325A (ja) | 2004-10-21 |
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