JP6284922B2 - 発光ファイバー - Google Patents
発光ファイバー Download PDFInfo
- Publication number
- JP6284922B2 JP6284922B2 JP2015236748A JP2015236748A JP6284922B2 JP 6284922 B2 JP6284922 B2 JP 6284922B2 JP 2015236748 A JP2015236748 A JP 2015236748A JP 2015236748 A JP2015236748 A JP 2015236748A JP 6284922 B2 JP6284922 B2 JP 6284922B2
- Authority
- JP
- Japan
- Prior art keywords
- olefc
- treatment
- light
- skin
- fiber
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 229940072172 tetracycline antibiotic Drugs 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- NMFKEMBATXKZSP-UHFFFAOYSA-N thieno[3,2-b]thiophene Chemical compound S1C=CC2=C1C=CS2.S1C=CC2=C1C=CS2 NMFKEMBATXKZSP-UHFFFAOYSA-N 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 230000019432 tissue death Effects 0.000 description 1
- 150000001608 tolans Chemical class 0.000 description 1
- 239000003860 topical agent Substances 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 239000013306 transparent fiber Substances 0.000 description 1
- 230000008736 traumatic injury Effects 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- JFZKOODUSFUFIZ-UHFFFAOYSA-N trifluoro phosphate Chemical compound FOP(=O)(OF)OF JFZKOODUSFUFIZ-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- PYVOHVLEZJMINC-UHFFFAOYSA-N trihexyl(tetradecyl)phosphanium Chemical compound CCCCCCCCCCCCCC[P+](CCCCCC)(CCCCCC)CCCCCC PYVOHVLEZJMINC-UHFFFAOYSA-N 0.000 description 1
- IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
- 229960001082 trimethoprim Drugs 0.000 description 1
- 238000004402 ultra-violet photoelectron spectroscopy Methods 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 201000002282 venous insufficiency Diseases 0.000 description 1
- 229960003895 verteporfin Drugs 0.000 description 1
- ZQFGRJWRSLZCSQ-ZSFNYQMMSA-N verteporfin Chemical compound C=1C([C@@]2([C@H](C(=O)OC)C(=CC=C22)C(=O)OC)C)=NC2=CC(C(=C2C=C)C)=NC2=CC(C(=C2CCC(O)=O)C)=NC2=CC2=NC=1C(C)=C2CCC(=O)OC ZQFGRJWRSLZCSQ-ZSFNYQMMSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 238000004832 voltammetry Methods 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 230000037331 wrinkle reduction Effects 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- 229960001296 zinc oxide Drugs 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Classifications
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Description
a)第1の電極と、
b)発光層と、
c)第2の電極と
を備える。
接触要素は、任意の導電性金属、例えば、アルミニウムまたは銅を含み得る。湿気遮蔽層50は、湿気が有機層30に浸透することを防ぐ、任意の物質、例えば、SiO2、Si3N4またはオキシ窒化ケイ素を含み得る。封止物質60は、シリコーンまたはエポキシを含み得る。
a)外側の第1の電極20を有するファイバーコア10(図1参照)と;
b)少なくとも1種の有機エレクトロルミネセンス化合物と少なくとも1種のイオン種とを含み、前記第1の電極20の外側表面上に位置する、発光層30と;
c)有機発光層30上に位置する輻射線透過性の第2の電極40と
を含む。
Ar1は、同じであっても異なっていてもよく、異なる繰返し単位にある場合は独立に、単結合、または任意に置換された単核もしくは多核アリール基を表し、
Ar2は、同じであっても異なっていてもよく、異なる繰返し単位にある場合は独立に、任意に置換された単核もしくは多核アリール基を表し、
Ar3は、同じであっても異なっていてもよく、異なる繰返し単位にある場合は独立に、任意に置換された単核または多核アリール基を表し、
mは、1,2または3である。
Rは、出現する毎に、同じであっても異なっていてもよく、H、置換もしくは無置換の芳香族または複素芳香族基、アルキル、シクロアルキル、アルコキシ、アラルキル、アリールオキシ、アリールチオ、アルコキシカルボニル、シリル、カルボキシ基、ハロゲン原子、シアノ基、ニトロ基、あるいはヒドロキシ基から選択され、
rは、0、1、2、3または4であり、また
sは、0、1、2、3、4または5である。
T1およびT2は、互いに独立に、チオフェン、セレノフェン、チエノ[2,3b]チオフェン、チエノ[3,2b]チオフェン、ジチエノチオフェン、ピロール、アニリンから選択され、これらの全ては、R5により任意に置換されており、
R5は、出現する毎に互いに独立に、ハロゲン、−CN、−NC、−NCO、−NCS、−OCN、SCN、C(=O)NR0R00、−C(=O)X、−C(=O)R0、−NH2、−NR0R00、SH、SR0、−SO3H、−SO2R0、−OH、−NO2、−CF3、−SF5、任意に置換されたシリル、または、1〜40個のC原子を有するカルビルもしくはヒドロカルビルから選択され、これは、任意に置換され、および1個以上のヘテロ原子を任意に含み、
Ar4およびAr5は、互いに独立に、単核もしくは多核アリールまたはヘテロアリールであり、これは、任意に置換されており、また隣接するチオフェンもしくはセレノフェン基の一方または両方の2,3位に任意に縮合しており、
cおよびeは、互いに独立に、0、1、2、3または4で、1<c+e≦6であり、
dおよびfは、互いに独立に、0、1、2、3または4である。
A、BおよびB’は、互いに独立に、また複数個が出現する場合には互いに独立に、2価の基であり、好ましくは−CR1R2−、−NR1−、−PR1−、−O−、−S−、−SO−、−SO2−、−CO−、−CS−、−CSe−、−P(=O)R1−、−P(=S)R1−、および−SiR1R2−から選択され、
R1およびR2は、互いに独立に、H、ハロゲン、−CN、−NC、−NCO、−NCS、−OCN、−SCN、−C(=O)NR0R00、−C(=O)X、−C(=O)R0、−NH2、−NR0R00、−SH、−SR0、−SO3H、−SO2R0、−OH、−NO2、−CF3、−SF5、任意に置換されたシリル、または1〜40個のC原子を有するカルビルもしくはヒドロカルビルから選択される互いに同じまたは異なる基であり、これは任意に置換されており、また1個以上のヘテロ原子を任意に含み、任意に、基R1およびR2は、それらが結び付いているフルオレン部分とスピロ基を形成し、
Xは、ハロゲンであり、
R0およびR00は、互いに独立に、H、あるいは1個以上のヘテロ原子を任意に含み、任意に置換された、カルビルもしくはヒドロカルビル基であり、
各gは、独立に、0または1であって、同じサブ単位における対応する各hは、0または1のもう一方のものであり、
mは、整数≧1であり、
Ar1およびAr2は、互いに独立に、単核もしくは多核のアリールまたはヘテロアリールであり、これは、任意に置換され、また、インデノフルオレン基の7,8−位または8,9−位に任意に縮合し、
aおよびbは、互いに独立に、0または1である。
Lは、H、ハロゲン、または任意にフッ素化された、1から12個のC原子を有する線状もしくは分岐状のアルキルまたはアルコキシであり、好ましくは、H、F、メチル、i−プロピル、t−ブチル、n−ペントキシ、またはトリフルオロメチルであり、また
L’は、任意にフッ素化された、1から12個のC原子を有する線状もしくは分岐状のアルキルまたはアルコキシであり、好ましくは、n−オクチルまたはn−オクチルオキシである。
式中、
Ar4、Ar5、Ar6は、出現する毎に、同じかまたは異なり、5から30個の芳香環原子を有するアリールまたはヘテロアリールであり、これは、1つまたは複数の基によって置換されていてもよく、
pは、1、2、または3であり、
Ar4、Ar5およびAr6におけるπ−電子の合計は、p=1の場合、少なくとも30個であり、p=2の場合、少なくとも36個であり、p=3の場合、少なくとも42個である。
式中、M、L、およびnは、前記文献と同じ定義である。好ましくは、MはZnであり、Lはキノリネートであり、nは、2、3または4である。特に非常に好ましいのは、[Znq2]2、[Znq2]3、および[Znq2]4である。
ETMは、通常、低く、典型的には−2.7eVより低いLUMOを有する。
R1からR6は、互いに独立に、1〜20個のC原子を有する線状もしくは多分岐状(hyperbranched)アルキル残基、2〜20個のC原子および1つまたは複数の非共役2重結合を有する線状もしくは多分岐状アルケニル残基、2〜20個のC原子および1つまたは複数の非共役3重結合を有する線状もしくは多分岐状アルキニル残基、3〜7個のC原子を有する飽和、部分飽和もしくは完全飽和シクロアルキル(これは、1〜6個のC原子を有するアルキル基によりさらに置換されていてもよい)から選択でき、ここで、1つまたは複数の置換基Rは、ハロゲン、特に、−Fおよび/または−Clにより部分的もしくは完全に置換されていてもよく、あるいは、−OR’、−CN、−C(O)OH、−C(O)NR’2、−SO2NR’2、−SO2OH、−SO2X、−NO2により部分的に置換されていてもよく、R1からR6の非隣接、非α−炭素原子の1個または2個は、−O−、−S−、−S(O)−、−SO2−、−N+R’2−、−C(O)NR’−、−SO2NR’−、および−P(O)R’−から選択される基により置換されていてもよく、式中、R’=H、無置換または−Fにより部分的もしくは完全に置換されたC1〜C6−アルキル、C3〜C7−シクロアルキル、無置換もしくは置換フェニルであり、また、X=ハロゲンである。
n=1から8であり、
RFは、式(CmF2m−x+1Hx)のフッ素化アルキル(m=1から12、x=0から7であり、m=1では、x=0から2である)、および/またはフッ素化(さらに、パーフルオロ化)アリールもしくはアルキル−アリールである。
ガラスファイバーに通常用いられる洗浄プロセスが、OLEFCのファイバーコアにもまた用いられ得る:ファイバーコアは、溶媒により脱脂され、次いで、UV−オゾン環境に曝すことによって洗浄される。特別な洗浄プロセスが、用いられる特別なファイバーコアに合わせて、採用されることがある。
この波長は、好ましくは290〜400nm、特に好ましくは300〜330nmの範囲にある。この目的のために特に好ましい1つの波長は、311nmである。
[例1]
物質
次のポリマーを、スズキカップリングを用いることによって合成する。反応は、当業者によく知られている合成方法に従って実施できる。この方法は、例えば、WO2003/048225に記載されている。
OLEFCの製造
本発明において用いられるファイバーコア10は、固い(hard)ポリマーで被覆されたシリカ光ファイバー(CeramOptec Industries,Inc.による)であり、直径400μmのシリカコアと、被覆物として25μmのポリイミドとを有する。電極の堆積の前に、ファイバーは、順次、洗浄剤で拭き取り、脱イオン水で洗い、トリクロロエチレン、アセトン、次にイソプロピルアルコール中で超音波洗浄することによって洗浄する。
アノード20を、10−7Torrで真空熱蒸着を用い、シャドウマスクを通してコンフォーマルに堆積させる。ファイバーを、蒸着の間、60rpmの速度で、軸の回りに回転させる。それから、150nmのAlを、第1の電極(アノード)として、洗浄したファイバーコア10に蒸着する。
PEDOT(Baytron P AI 4083)を、浸漬コーティングし、次に、180℃で10分間加熱することによって、厚さ80nmのバッファ層または正孔注入層(HIL)として、ファイバー上に堆積させる;厚さは、濃度および浸漬コーティングの間の引き上げ速度を通じて制御できる。次いで、残留水を除去するために、ファイバーを、180℃で10分間加熱する。
次いで、中間層ポリマーP3を、0.1〜0.5wt%の濃度で含むトルエン溶液により浸漬コーティングすることによって、中間層32をコーティングし、約40nmの厚さを有する層を得る。
次に、発光層(EML)33を、発光ポリマー(EM)とPEOとLiTfとを、EM:PEO:LiTf=1:1:0.25の質量比で含むクロロベンゼン溶液に浸漬コーティングすることによって、コーティングし、約500nmの厚さを有する層を得る。組成物の濃度は、表1に列挙されている。
Agからなるカソード40を、25nmの厚さで、発光層上に、熱真空蒸着により、シャドウマスクを通してコンフォーマルに堆積させる;ファイバーに沿うアノードとカソードの両方は、1セグメントにおいて、4cmの長さを有する。それらは、両方の電極が、長さで約3cm、重なるように互いにずらして配置され、3cmの長さは、また、ファイバー上の発光部分に相当する。
ファイバーを、5cmの長さのセグメントに切断する。接触できる外皮のないアノードを得るために、切断したファイバーの一方の端(ここには、カソードが堆積していない)を、最初に、トルエンで、次に、エタノールで洗って、ポリマーおよびPEDOTを除去する。
OLEFCを含むプラスターの製造
透明で軟質であるポリ(エチレンナフタレート)(PEN)箔を、プラスターの製造のための基材として用いる。
Claims (22)
- 少なくとも1種のイオン種を含む有機発光電気化学セル(OLEC)であって、前記OLECはファイバーの形態を有する(OLEFC)ことを特徴とし、
OLECは、
a)外側の第1の電極を有するファイバーコアと;
b)第1の電極上に配置された正孔注入層と;
c)正孔注入層上に配置された下記式のコポリマーを含む中間層と;
d)ポリマーである少なくとも1種の有機エレクトロルミネセンス化合物と移動性である少なくとも1種のイオン種とを含み、中間層上に配置された発光層(EML)と;
e)前記有機発光層上に配置された輻射線透過性の第2の電極と
を含む、OLEFC。 - 前記OLEFCが軟質または硬質のファイバーコアを含むことを特徴とする、請求項1に記載のOLEFC。
- 前記ファイバーが、円形、楕円形もしくは多角形の断面またはこれらの組合せを有することを特徴とする、請求項1または2に記載のOLEFC。
- OLEFCが、蛍光発光物質、燐光発光物質、および発光性有機金属錯体から選択される少なくとも1種の有機エレクトロルミネセンス化合物を含むことを特徴とする、請求項1〜3の何れか1項に記載のOLEFC。
- 有機エレクトロルミネセンス物質が、少なくとも1種のホスト物質と少なくとも1種の発光物質とを含むことを特徴とする、請求項1〜4の何れか1項に記載のOLEFC。
- ホスト物質が、アントラセン、ベンゾアントラセン、ケトン、カルバゾール、トリアリールアミン、インデノフルオレン、フルオレン、スピロビフルオレン、フェナントレン、ジヒドロフェナントレン、チオフェン、トリアジン、イミダゾール、これらの異性体および誘導体から選択されることを特徴とする、請求項5に記載のOLEFC。
- 前記OLEFCが、正孔輸送物質(HTM)、正孔注入物質(HIM)、電子輸送物質(ETM)、および電子注入物質(EIM)から選択される、少なくとも1種のさらなる機能物質を含むことを特徴とする、請求項1〜6の何れか1項に記載のOLEFC。
- 前記OLEFCが、少なくとも1種のイオン性遷移金属錯体(iTMC)を含むことを特徴とする、請求項1〜7の何れか1項に記載のOLEFC。
- 請求項1〜8の何れか1項に記載のOLEFCの製造方法であって、当該方法が、次のステップ:
a)前記ファイバーコアの洗浄と;
b)金属のコンフォーマル蒸着(conformal evaporation)による、または導電性物質を含む溶液もしくは配合物をコーティングすることによる、前記第1の電極の堆積と;
c)正孔注入層の堆積と;
d)下記式のコポリマーを含む中間層の堆積と;
f)前記第2の電極の堆積と;
g)前記ファイバーを含むデバイスの任意の封止と
を含むことを特徴とする方法。 - コーティングが、は浸漬コーティングもしくはスプレーコーティングである請求項9に記載の方法。
- 請求項1〜8の何れか1項に記載の少なくとも1種のOLEFCを含むキャンバス。
- 請求項1〜8の何れか1項に記載の少なくとも1種のOLEFCまたは請求項11に記載のキャンバスを含むデバイス。
- フラットパネル、曲面パネル、プラスター、包帯、毛布、寝袋、スリーブ、植込み型プローブ、経鼻胃管、胸郭ドレイン、パッド、ステント、パッチ、任意の種類の衣類、および口内の少なくとも1本の歯を覆うデバイスであることを特徴とする、請求項12に記載のデバイス。
- 一般照明における使用、ディスプレイバックライトとしての使用、および情報ディスプレイとしての使用のための、請求項12または13に記載のデバイス。
- 疾患および/または美容上の状態の治療および/または予防および/または診断のための、請求項12または13に記載のデバイス。
- 皮膚疾患および/または美容上の皮膚の状態の治療および/または予防および/または診断のための、請求項15に記載のデバイス。
- ざ瘡、乾癬、湿疹、皮膚炎、アトピー性皮膚炎、浮腫、白斑、皮膚の脱感作、ボーエン病、腫瘍、前癌性腫瘍、悪性腫瘍、基底細胞癌、扁平上皮細胞癌、二次転移、皮膚T細胞リンパ腫、日光角化症、ヒ素角化症、放射線皮膚炎およびセルライトから選択される皮膚疾患および/または美容上の皮膚の状態の治療および/または予防および/または診断のための、請求項15または16に記載のデバイス。
- 感染症、並びに炎症性、神経学的および心理学的な疾患および/または状態の治療および/または予防および/または診断のための、請求項15〜17の何れか1項に記載のデバイス。
- 水、飲用水、ソフトドリンク、飲料、食料品および栄養物の消毒のための、請求項15〜18の何れか1項に記載のデバイス。
- 光線力学療法(PDT)における適用において使用するための、および/または黄疸およびクリグラー・ナジャー症候群の治療および/または予防のための、請求項15〜19何れか1項に記載のデバイス。
- 疾患および/または美容上の状態の治療および/または予防および/または診断のためのデバイスを製造するための、請求項1〜8の何れか1項に記載のOLEFC。
- 請求項1〜8何れか1項に記載のOLEFCまたは請求項11記載のキャンバスまたは請求項12または13記載のデバイスの非治療的美容のための使用。
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2011
- 2011-02-15 JP JP2012556398A patent/JP2013522816A/ja not_active Withdrawn
- 2011-02-15 US US13/634,078 patent/US9373807B2/en not_active Expired - Fee Related
- 2011-02-15 KR KR1020127026514A patent/KR101757016B1/ko active IP Right Grant
- 2011-02-15 EP EP11704549A patent/EP2545600A2/en not_active Withdrawn
- 2011-02-15 WO PCT/EP2011/000705 patent/WO2011110275A2/en active Application Filing
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2016
- 2016-05-17 US US15/156,768 patent/US20160256053A1/en not_active Abandoned
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Cited By (1)
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JP2018029067A (ja) * | 2010-03-11 | 2018-02-22 | メルク パテント ゲーエムベーハー | 発光ファイバー |
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EP2545600A2 (en) | 2013-01-16 |
US20130006118A1 (en) | 2013-01-03 |
WO2011110275A2 (en) | 2011-09-15 |
US20160256053A1 (en) | 2016-09-08 |
US9373807B2 (en) | 2016-06-21 |
JP2018029067A (ja) | 2018-02-22 |
KR101757016B1 (ko) | 2017-07-11 |
WO2011110275A3 (en) | 2011-12-01 |
JP2013522816A (ja) | 2013-06-13 |
JP2016119458A (ja) | 2016-06-30 |
KR20130018762A (ko) | 2013-02-25 |
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