JP2009256679A - フルオレン含有ポリマー及びエレクトロルミネッセンスデバイス - Google Patents
フルオレン含有ポリマー及びエレクトロルミネッセンスデバイス Download PDFInfo
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- JP2009256679A JP2009256679A JP2009142786A JP2009142786A JP2009256679A JP 2009256679 A JP2009256679 A JP 2009256679A JP 2009142786 A JP2009142786 A JP 2009142786A JP 2009142786 A JP2009142786 A JP 2009142786A JP 2009256679 A JP2009256679 A JP 2009256679A
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- 229920000642 polymer Polymers 0.000 title claims abstract description 57
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- 238000005401 electroluminescence Methods 0.000 title abstract 3
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- 239000010406 cathode material Substances 0.000 claims description 8
- 239000010405 anode material Substances 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 239000000178 monomer Substances 0.000 abstract description 15
- 229920000547 conjugated polymer Polymers 0.000 abstract description 2
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- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
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- 125000003277 amino group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
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- 150000001502 aryl halides Chemical class 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
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- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 2
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- ZVFJWYZMQAEBMO-UHFFFAOYSA-N 1h-benzo[h]quinolin-10-one Chemical compound C1=CNC2=C3C(=O)C=CC=C3C=CC2=C1 ZVFJWYZMQAEBMO-UHFFFAOYSA-N 0.000 description 1
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- YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000004655 tetrazenes Chemical class 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
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Abstract
【解決手段】フルオレン含有モノマー由来の特定な基を10〜90重量パーセントと、アミン含有モノマー由来の6種より選ばれる特定な基又はこれらの混合物を10〜90重量パーセント含むコポリマーであって、第一のコポリマーを1〜99重量パーセント、及びフルオレン含有モノマー由来の基及び所望によりアミン含有モノマー由来の6種より選ばれる基以外の共役基を含む少なくとも1種のポリマーを99〜1重量パーセントを含む組成物のフィルムであるエレクトロルミネッセンスデバイス。
【選択図】なし
Description
式(I)〜(VI)の基を含むポリマーは、適当な方法によって製造してよいが、好ましくは以下に記載の方法の1つによって製造する。芳香族ボロネートと臭素の縮合反応(通常、Suzuki反応と呼ばれている)は、N.Miyaua and A.Suzuki,Chemical Reviews,Vol.95,pp.457-2483(1995)に記載されている。この反応は高分子量ポリマー及びコポリマーの製造に適用することができる。ポリマーを製造するため、式(I)〜(VI)より選ばれる内部基を有するジブロミド、又はその混合物を等量の、式(I)〜(VI)より選ばれる内部基を有するジボロン酸(diboronic acid)もしくはジボロネート、又はこれらの混合物と、Pd及びトリフェニルホスフィンの触媒作用の下で反応させる。この反応は通常70℃〜120℃において、トルエンのような芳香族炭化水素溶剤中で行われる。他の溶剤、例えばジメチルホルムアミド及びテトラヒドロフランも単独で又は芳香族炭化水素との混合物として用いてよい。HBrスカベンジャーとして水性塩基、好ましくは炭酸ナトリウムもしくは炭酸水素ナトリウムを用いる。反応体の反応性によって、重合反応は2〜100時間かかる。他の反応条件は、T.I.Wallow and B.M.Novak,Journal of Organic Chemistry,Vol.59,pp.5034-5037(1994)、M.Remmers,M.Schulze and G.Wegner,Macromolecular Rapid Communications,Vol.17,pp.239-252(1996)、及び米国特許第5,777,070号に記載されている。式(I)〜(VI)より選ばれる内部基の1つのタイプを有するジブロミドを式(I)〜(VI)より選ばれる異なる内部基を有する硼素含有モノマーと反応させた場合に他のコポリマーが得られる。
本発明のポリマーの製造において有効なフルオレン含有モノマーは下式の化合物を含む。
Zは独立に−B(OH)2、−B(OR4)2又は
本発明の第一の態様のコポリマーの合成用のアミン含有モノマーは、米国特許第5,728,801号に記載の方法によって製造される。
第二の態様において、本発明は(a)本発明の第一の態様のコポリマーを1〜99重量パーセント、及び(b)式(I)の基及び所望により式(II)、(III)、(IV)、(V)、及び(VI)の基以外の共役基を含む少なくとも1種のポリマーを99〜1重量パーセント、含む組成物である。
本発明の他の態様は本発明のポリマーより形成されたフィルムである。このフィルムはポリマー発光ダイオードに用いることができる。好ましくは、このフィルムは発光層又は電荷キャリヤ輸送層として用いられる。このポリマーは電子デバイスの保護コーティングとして又は蛍光コーティングとしても用いることができる。このコーティングもしくはフィルムの厚さは用途によって異なる。通常、この厚さは0.01〜200ミクロンである。このコーティングを蛍光コーティングとして用いる場合、このコーティングもしくはフィルムの厚さは50〜200ミクロンである。このコーティングを電子保護層として用いる場合、このコーティングの厚さは5〜20ミクロンである。このコーティングをポリマー発光ダイオードに用いる場合、形成される層の厚さは0.05〜2ミクロンである。本発明のオリゴマーもしくはポリマーは優れたピンホールのないもしくは欠陥のないフィルムを形成する。このフィルムは、スピンコーティング、スプレーコーティング、浸漬コーティング及びローラーコーティングを含む公知の方法により形成することができる。このコーティングは、組成物を基材に塗布し、この塗布した組成物をフィルムが形成する条件に付すことを含む方法によって形成される。フィルムを形成する条件は塗布法によって異なる。好ましくは、溶液加工法が用いられ、通常の有機溶剤中の所望のポリマーの0.1〜10重量パーセント溶液が用いられる。薄コーティング用には、フィルム形成組成物は0.5〜5.0重量パーセントのオリゴマーもしくはポリマーを含むことが好ましい。次いでこの組成物は所望の方法により適当な基材に塗布され、溶剤が蒸発される。残留溶剤は真空及び/又は加熱によって除去される。溶剤の沸点が低い場合は、溶液濃度が低いこと、例えば0.1〜2パーセントであることが望ましい。溶剤の沸点が高い場合は、高濃度、例えば3〜10パーセントが望ましい。
この実施例におけるアミンコポリマーは式(V)〜(XII)の構造を有する。この実施例において命名する他のポリマーは以下の構造を有する。
ITOガラス上にポリマーブレンドのキシレン溶液をスピンコーティングし、次いでカルシウムカソードを付着させることによって単一層エレクトロルミネッセンスデバイスを製造した。このポリマーブレンド成分は5BTF8及びアミンコポリマーである。1000Cd/m2の輝度におけるデバイス操作パラメータを、式πL(10JV)(Lは1000Cd/m2である)によって得られる効率、すなわちルーメン/ワットと共に表1に示す。バイアス電圧(V)は1000Cd/m2の輝度が得られる際の電圧であり、同様に電流密度(J)は1000Cd/m2におけるデバイスの単位面積あたりの電流であり、mA/cm2で示す。
N,N-ジメチルホルムアミド中のポリマー溶液から第一の層(BFAもしくはPFA)をスピンコーティングすることによって2相デバイスを製造した。形成されたフィルムを真空中60〜90℃で乾燥した。ポリマーもしくはポリマーブレンドのキシレン溶液からスピンコーティングによって第二の層を形成した。各場合における層2は発光層である。
Claims (12)
- (a)請求項1記載のコポリマーを1〜99重量パーセントと(b)式(I)の基及び所望により式(II)、(III)、(IV)、(V)もしくは(VI)の基以外の共役基を含む少なくとも1種のポリマーを99〜1重量パーセント含む組成物。
- アノード材料とカソード材料の間に配置され、少なくとも1つがエレクトロルミネッセンス有機フィルムである少なくとも1つの有機フィルムを含むエレクトロルミネッセンスデバイスであって、電圧を印加すると、前記エレクトロルミネッセンス有機フィルムがこのデバイスの透明な外部部分を通して通過する可視光を発し、前記少なくとも1つの有機フィルムが請求項1記載のコポリマーのフィルムであるエレクトロルミネッセンスデバイス。
- アノード材料とカソード材料の間に配置され、少なくとも1つがエレクトロルミネッセンス有機フィルムである少なくとも1つの有機フィルムを含むエレクトロルミネッセンスデバイスであって、電圧を印加すると、前記エレクトロルミネッセンス有機フィルムがこのデバイスの透明な外部部分を通して通過する可視光を発し、前記少なくとも1つの有機フィルムが請求項7記載の組成物のフィルムであるエレクトロルミネッセンスデバイス。
下式で表されるポリマー。 - アノードとカソードの間に配置された有機フィルムを含むエレクトロルミネッセンスデバイスであって、電圧を印加すると、前記有機フィルムからこのデバイスの透明な外部部分を通して発光し、前記有機フィルムの少なくとも1つの成分が請求項1記載のコポリマーであるエレクトロルミネッセンスデバイス。
- 前記有機フィルムが3級アミンポリマーもしくはコポリマーをさらに含み、アミン部分の窒素原子の少なくとも一部がポリマー主鎖の一部である、請求項10記載のデバイス。
- 前記有機フィルムがアミンポリマーもしくはコポリマーをさらに含み、アミン部分の窒素原子がポリマー主鎖の一体部分である、請求項10記載のデバイス。
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US5708130A (en) | 1995-07-28 | 1998-01-13 | The Dow Chemical Company | 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers |
DE69608446T3 (de) * | 1995-07-28 | 2010-03-11 | Sumitomo Chemical Company, Ltd. | 2,7-aryl-9-substituierte fluorene und 9-substituierte fluorenoligomere und polymere |
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US11910697B2 (en) | 2020-09-09 | 2024-02-20 | Samsung Electronics Co., Ltd. | Copolymer, electroluminescence device material including copolymer, and electroluminescence device |
Also Published As
Publication number | Publication date |
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CA2294485C (en) | 2008-02-19 |
US20010026878A1 (en) | 2001-10-04 |
CA2294485A1 (en) | 1999-10-28 |
DE69908522T2 (de) | 2004-04-15 |
EP0988337B2 (en) | 2006-11-02 |
CN100341922C (zh) | 2007-10-10 |
US6309763B1 (en) | 2001-10-30 |
TWI243187B (en) | 2005-11-11 |
JP2002506481A (ja) | 2002-02-26 |
DE69908522D1 (de) | 2003-07-10 |
US6605373B2 (en) | 2003-08-12 |
JP5300612B2 (ja) | 2013-09-25 |
DE69908522T3 (de) | 2007-05-24 |
WO1999054385A1 (en) | 1999-10-28 |
KR100575382B1 (ko) | 2006-05-03 |
CN101058672B (zh) | 2012-07-04 |
CN1263542A (zh) | 2000-08-16 |
EP0988337B1 (en) | 2003-06-04 |
KR20010014061A (ko) | 2001-02-26 |
EP0988337A1 (en) | 2000-03-29 |
CN101058672A (zh) | 2007-10-24 |
JP4375820B2 (ja) | 2009-12-02 |
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