JP5219371B2 - 可溶性共役ポリマーを含む方法及びデバイス - Google Patents
可溶性共役ポリマーを含む方法及びデバイス Download PDFInfo
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- JP5219371B2 JP5219371B2 JP2006527071A JP2006527071A JP5219371B2 JP 5219371 B2 JP5219371 B2 JP 5219371B2 JP 2006527071 A JP2006527071 A JP 2006527071A JP 2006527071 A JP2006527071 A JP 2006527071A JP 5219371 B2 JP5219371 B2 JP 5219371B2
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
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- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 125000002463 lignoceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002493 microarray Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
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- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Chemical class C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
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- 229920000620 organic polymer Polymers 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
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- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 239000004633 polyglycolic acid Substances 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
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- 229920000131 polyvinylidene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical class COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000004054 semiconductor nanocrystal Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical class OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005032 thiofuranyl group Chemical group S1C(=CC=C1)* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229930192474 thiophene Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
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- 238000007740 vapor deposition Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Images
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Description
本発明を説明する際、以下の用語が使用され、下記のように定義されることを意図する。
極性媒体中に可溶性である共役ポリマー(CP)が提供され、本明細書に記載されている実施形態において使用され得る。CPは、極性媒体中でのポリマー溶解度を高めるためにポリマーサブユニットに連結させる可溶化官能基として極性基を含む。CPのサブユニットのいずれかまたは全てが1つ以上のペンダント可溶化基を含み得る。極性基の例には、CPに対して1つ以上の双極子モーメントを導入するもの、例えばハライド、ヒドロキシル、アミン、アミド、シアノ、カルボン酸及びチオールが含まれる。
共役ポリマーは、少なくとも1つの極性溶媒を含む極性媒体中に可溶性である。“極性”とは、正味の双極子モーメントを有することを意味する。極性溶媒の例には、ジメチルスルホキシド、ジメチルホルムアミド、ギ酸、酢酸、酢酸エチル、水、アルコール及びポリアルコール、特に低級アルコール(C1-4)、具体的にはメタノールが含まれる。好ましくは、極性溶媒は少なくともエタノールまたは酢酸エチルの極性を有する。幾つかの実施形態では、CPを溶解させるために使用される極性溶媒は、CPを堆積させようとする第2共役ポリマーを溶解できない能力に基づいて選択される。
本明細書に記載されているCPは各種方法で使用され得る。特に興味深い方法には、電子デバイス、特に複数の共役ポリマー層を含むデバイスへのCPの堆積が含まれる。所定のデバイスにおいて任意の各種堆積方法が使用され得るが、この方法には真空スパッタリング(RFまたはマグネトロン)、電子ビーム蒸発、熱蒸着、化学析出、昇華及び溶液加工方法が含まれるが、これらに限定されない。本発明の可溶性極性ポリマーを堆積させるためには当技術分野で公知または発見され得る任意の堆積方法が使用され得るが、溶液方法が現在好ましい。
CPは、光電子または電子デバイス、バイオセンサー、ダイオード(フォトダイオード及び発光ダイオード(LED)を含む)、光電子半導体チップ、半導体薄膜及びチップを含めた任意の各種製品に組み込まれ得、アレイまたはマイクロアレイの形態で使用され得る。ポリマーはポリマーフォトスイッチに組み込まれ得る。ポリマーは光信号を電気インパルスに変換するためのオプチカルインターコネクトまたはトランスデューサーに組み込まれ得る。CPは液晶材料として機能し得る。CPは電気化学セル中の電極として、エレクトロクロミックディスプレー中の導電層として、電解効果トランジスターとして、及びショットキーダイオードとして使用され得る。
(1)ETLの最低空分子軌道(LUMO)は、(電子が注入され得るように)発光半導体ポリマーのπ*帯に近いかまたはそのπ*帯に等しいエネルギーでなければならない;そして
(2)電子注入材料をキャスティングするのに使用される溶媒は下にある発光ポリマーを溶解してはならない。
1実施形態では、ITO/PEDOT/発光ポリマー/ETL/Ba/Alのデバイス構成において、発光層として有機溶媒中の溶液からキャストした半導体ポリマーを、電子輸送層(ETL)として水溶性(または、メタノール可溶性)共役コポリマーを用いてポリマー発光ダイオード(PLED)を作製した。その結果、ETLを含むデバイスは、有意に低いターンオン電圧と、より高い輝度及び向上した発光効率を示した。図面参照。
PLEDの作製
水溶性共役コポリマーのポリ{[9,9-ビス(6’-(N,N,N-トリメチルアンモニウム)ヘキシル)-フッ素-2,7-ジイル]-alt-[2,5-ビス(p-フェニレン)-1,3,4-オキサジアゾール]}(PFON+(CH3)3I--PBD)をパラジウム触媒スズキカップリング反応を用いて合成し[13,14]、電子輸送層(ETL)として使用した。ポリ(9,9-ジヘキシルフルオレン-コ-ベンゾチアジアゾール)(PFO-BT)もスズキカップリング反応を用いて合成した[15]。ポリ(9,9-ジオクチルフルオレニル-2,7-ジイル)(PFO)及びポリ[2-メトキシ-5-(2-エチル-ヘキシルオキシ)-1,4-フェニレンビニレン](MEH-PPV)はカナダに所在のAmerican Dye Source,Inc.から購入した。PFO、PFO-BT、MEH-PPV及びPFON+(CH3)3I--PBDの分子構造を以下に示す。
水溶性CCPを含むPLEDのキャラクタリゼーション
PFO及びPFO/ETLを用いて作製したデバイスの電流密度対電圧、及び輝度対電圧特性を図2に示す。PFO/ETLデバイスは〜3Vでオンになった(ターンオン電圧は0.1cd/m2の輝度での電圧と規定される)が、ETLなしで作製したPFOデバイス[18]の場合のターンオン電圧は〜5Vであった。6Vで、PFO/ETLデバイスから得られる輝度(L)はL=3450cd/m2であり、ETLなしのデバイスの場合L=30cd/m2である。
多層PLED中の電子輸送層として、水溶性及びメタノール可溶性の共役ポリマー、すなわちPFON+(CH3)3I--PBDを使用した。メタノールの溶液からETLをキャストし、有機溶媒の溶液から発光層をキャストすることにより、界面混合が避けられた。発光層として青色、緑色または赤色発光半導体ポリマー、ETLとしてPFON+(CH3)3I--PBDを用いて、性能の有意な向上が立証された。より重要なことは、我々の結果は多層PLEDが複数の溶液を堆積させることにより作製され得ることを示している。
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Claims (21)
- 水溶性カチオン性共役ポリマーである第1材料及び第1溶媒からなる第1溶液を用意し、ここで前記第1溶媒は少なくとも1つの極性溶媒を含み、第2材料及び第2溶媒からなる第2溶液を用意し、ここで前記第2溶媒は少なくとも1つの低極性の有機溶媒を含み、基板上に前記第1または第2溶液の一方の第1層を堆積させ、前記第1層上に前記第1または第2溶液の他方の第2層を堆積させることを含む、基板上に材料の隣接層を形成する方法であって、前記共役ポリマーが、該共役ポリマーに連結される、ペンダント可溶化基としての極性基を含む前記方法。
- 第1溶媒が水からなる請求項1に記載の方法。
- 第1溶液が界面活性剤を含む請求項1に記載の方法。
- 基板上への第1溶液の堆積がスピンキャスティングを含む請求項1に記載の方法。
- 基板がフィルムである請求項1に記載の方法。
- カチオン性水溶性共役ポリマーを溶媒中に含む第1溶液を用意し、ここで前記共役ポリマーは、該共役ポリマーに連結される、ペンダント可溶化基としての極性基を含み、前記溶媒に溶解しない材料からなる基板を用意し、前記基板上に前記第1溶液を堆積させることを含む、基板へのポリマー層の付加方法。
- 溶媒が水からなる請求項6に記載の方法。
- 基板上への第1溶液の堆積がスピンキャスティングを含む請求項6に記載の方法。
- 基板がフィルムである請求項6に記載の方法。
- 水溶性カチオン性共役ポリマーの層を含む多層電子デバイス。
- 基板が硬質である請求項1に記載の方法。
- 基板が硬質である請求項6に記載の方法。
- 請求項1に記載の方法により作製したポリマー層を含む基板。
- 請求項13に記載の基板を含む電気部品。
- 部品がレーザー、フォトダイオード、発光ダイオード(LED)、オプチカルインターコネクト、トランスデューサー、半導体チップ、半導体薄膜及びポリマーフォトスイッチからなる群から選択される請求項14に記載の電気部品。
- 部品がフォトダイオードである請求項15に記載の電気部品。
- 部品が発光ダイオード(LED)である請求項15に記載の電気部品。
- 部品がレーザーである請求項15に記載の電気部品。
- 部品がトランスデューサーである請求項15に記載の電気部品。
- 部品がポリマーフォトスイッチである請求項15に記載の電気部品。
- 極性溶媒が少なくともエタノールまたは酢酸エチルの極性を有する請求項1に記載の方法。
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US9017766B2 (en) | 2015-04-28 |
US20070274357A1 (en) | 2007-11-29 |
JP2007506283A (ja) | 2007-03-15 |
DE112004001737B4 (de) | 2016-08-11 |
WO2005056628A2 (en) | 2005-06-23 |
WO2005056628A3 (en) | 2006-03-09 |
DE112004001737T5 (de) | 2006-12-28 |
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