JP6649955B2 - ポリマー電荷移送層及びそれを収容する有機電子装置 - Google Patents
ポリマー電荷移送層及びそれを収容する有機電子装置 Download PDFInfo
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- JP6649955B2 JP6649955B2 JP2017535365A JP2017535365A JP6649955B2 JP 6649955 B2 JP6649955 B2 JP 6649955B2 JP 2017535365 A JP2017535365 A JP 2017535365A JP 2017535365 A JP2017535365 A JP 2017535365A JP 6649955 B2 JP6649955 B2 JP 6649955B2
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- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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Description
nが、2〜10であり、
R1〜R3が、それぞれ独立して、以下:水素;重水素;ヒドロカルビル、さらにC1−C100ヒドロカルビル、さらにC3−C100ヒドロカルビル、さらにC10−C100ヒドロカルビル、さらにC20−C100ヒドロカルビル、さらにC30−C100ヒドロカルビル;置換ヒドロカルビル、さらにC1−C100置換ヒドロカルビル、さらにC3−C100置換ヒドロカルビル、さらにC10−C100置換ヒドロカルビル、さらにC20−C100置換ヒドロカルビル、さらにC30−C100置換ヒドロカルビル;ヘテロヒドロカルビル、さらにC1−C100ヘテロヒドロカルビル、さらにC3−C100ヘテロヒドロカルビル、さらにC10−C100ヘテロヒドロカルビル、さらにC20−C100ヘテロヒドロカルビル、さらにC30−C100ヘテロヒドロカルビル;置換ヘテロヒドロカルビル、さらにC1−C100置換ヘテロヒドロカルビル、さらにC3−C100置換ヘテロヒドロカルビル、さらにC10−C100置換ヘテロヒドロカルビル、さらにC20−C100置換ヘテロヒドロカルビル、さらにC30−C100置換ヘテロヒドロカルビル;ハロゲン;シアノ;アリール、さらにC5−C100アリール、さらにC6−C100アリール、さらにC10−C100アリール、さらにC20−C100アリール、さらにC30−C100アリール;置換アリール、さらにC5−C100置換アリール、さらにC6−C100置換アリール、さらにC10−C100置換アリール、さらにC20−C100置換アリール、さらにC30−C100置換アリール;ヘテロアリール、さらにC5−C100ヘテロアリール、さらにC6−C10ヘテロアリール、さらにC10−C100ヘテロアリール、さらにC20−C100ヘテロアリール、さらにC30−C100ヘテロアリール;置換ヘテロアリール、さらにC5−C100置換ヘテロアリール、さらにC6−C100置換ヘテロアリール、さらにC10−C100置換ヘテロアリール、さらにC20−C100置換ヘテロアリール、さらにC30−C100置換ヘテロアリール;から選択され、
L1が、ヘテロ原子、芳香族部分、ヘテロ芳香族部分、C1−C100ヒドロカルビル、C1−C100置換ヒドロカルビル、C1−C100ヘテロヒドロカルビル、及びC1−C100置換ヘテロヒドロカルビルから選択され、
R1〜R3のうちの2つ以上が、1つ以上の環構造を任意に形成し得る。
R4〜R6及びR10〜R17が、それぞれ独立して、以下:水素、重水素、C1−C50ヒドロカルビル、C1−C50置換ヒドロカルビル、C1−C50ヘテロヒドロカルビル、C1−C50置換ヘテロヒドロカルビル、ハロゲン、シアノ、C5−C50アリール、C5−C50置換アリール、C5−C50ヘテロアリール、C5−C50置換ヘテロアリール;から選択され、
L2が、ヘテロ原子、芳香族部分、ヘテロ芳香族部分、C1−C100ヒドロカルビル、C1−C100置換ヒドロカルビル、C1−C100ヘテロヒドロカルビル、またはC1−C100置換ヘテロヒドロカルビルから選択され;L2の各化学基が、独立して、C、及びR10〜R17のうちの1つに結合し、
mが、2〜25であり、
R4〜R6及びR10〜R17のうちの2つ以上が、1つ以上の環構造を任意に形成し得る。
ポリマーは、構造Aを有するモノマーAを含み、
nが、2〜10であり、
R1〜R3が、それぞれ独立して、以下:水素;重水素;ヒドロカルビル、さらにC1−C100ヒドロカルビル、さらにC3−C100ヒドロカルビル、さらにC10−C100ヒドロカルビル、さらにC20−C100ヒドロカルビル、さらにC30−C100ヒドロカルビル;置換ヒドロカルビル、さらにC1−C100置換ヒドロカルビル、さらにC3−C100置換ヒドロカルビル、さらにC10−C100置換ヒドロカルビル、さらにC20−C100置換ヒドロカルビル、さらにC30−C100置換ヒドロカルビル;ヘテロヒドロカルビル、さらにC1−C100ヘテロヒドロカルビル、さらにC3−C100ヘテロヒドロカルビル、さらにC10−C100ヘテロヒドロカルビル、さらにC20−C100ヘテロヒドロカルビル、さらにC30−C100ヘテロヒドロカルビル;置換ヘテロヒドロカルビル、さらにC1−C100置換ヘテロヒドロカルビル、さらにC3−C100置換ヘテロヒドロカルビル、さらにC10−C100置換ヘテロヒドロカルビル、さらにC20−C100置換ヘテロヒドロカルビル、さらにC30−C100置換ヘテロヒドロカルビル;ハロゲン;シアノ;アリール、さらにC5−C100アリール、さらにC6−C100アリール、さらにC10−C100アリール、さらにC20−C100アリール、さらにC30−C100アリール;置換アリール、さらにC5−C100置換アリール、さらにC6−C100置換アリール、さらにC10−C100置換アリール、さらにC20−C100置換アリール、さらにC30−C100置換アリール;ヘテロアリール、さらにC5−C100ヘテロアリール、さらにC6−C10ヘテロアリール、さらにC10−C100ヘテロアリール、さらにC20−C100ヘテロアリール、さらにC30−C100ヘテロアリール;置換ヘテロアリール、さらにC5−C100置換ヘテロアリール、さらにC6−C100置換ヘテロアリール、さらにC10−C100置換ヘテロアリール、さらにC20−C100置換ヘテロアリール、さらにC30−C100置換ヘテロアリール;から選択され、
L1が、ヘテロ原子、芳香族部分、ヘテロ芳香族部分、C1−C100ヒドロカルビル、C1−C100置換ヒドロカルビル、C1−C100ヘテロヒドロカルビル、及びC1−C100置換ヘテロヒドロカルビルから選択され、
R1〜R3のうちの2つ以上が、1つ以上の環構造を任意に形成し得る。
L3が、ヘテロ原子、芳香族部分、ヘテロ芳香族部分、C1−C100ヒドロカルビル、C1−C100置換ヒドロカルビル、C1−C100ヘテロヒドロカルビル、及びC1−C100置換ヘテロヒドロカルビルから選択され、
xが、2〜10であり、
R7〜R9が、それぞれ独立して、以下:水素、重水素、C1−C50ヒドロカルビル、C1−C50置換ヒドロカルビル、C1−C50ヘテロヒドロカルビル、C1−C50置換ヘテロヒドロカルビル、ハロゲン、シアノ、C5−C50アリール、C5−C50置換アリール、C5−C50ヘテロアリール、及びC5−C50置換ヘテロアリール;から選択され、
R7〜R9のうちの2つ以上が、1つ以上の環構造を任意に形成し得る。
R4〜R6及びR10〜R17が、それぞれ独立して、以下:水素、重水素、C1−C50ヒドロカルビル、C1−C50置換ヒドロカルビル、C1−C50ヘテロヒドロカルビル、C1−C50置換ヘテロヒドロカルビル、ハロゲン、シアノ、C5−C50アリール、C5−C50置換アリール、C5−C50ヘテロアリール、C5−C50置換ヘテロアリール;から選択され、
L2が、ヘテロ原子、芳香族部分、ヘテロ芳香族部分、C1−C100ヒドロカルビル、C1−C100置換ヒドロカルビル、C1−C100ヘテロヒドロカルビル、またはC1−C100置換ヘテロヒドロカルビルから選択され;L2の各化学基が、独立して、C、及びR10〜R17のうちの1つに結合し、
mが、2〜25であり、
R4〜R6及びR10〜R17のうちの2つ以上が、1つ以上の環構造を任意に形成し得る。
本発明は、有機電子装置を作製する方法を提供する。本方法は、ポリマー電荷移送層溶液を提供することと、溶液プロセスによる有機電子装置の製造において使用されることが既知であるか、または提案されている有機溶媒のいずれかに、ポリマー電荷移送層溶液を溶解または分散させることと、を含む。そのような有機溶媒には、テトラヒドロフラン(THF)、シクロヘキサノン、クロロホルム、1,4−ジオキサン、アセトニトリル、酢酸エチル、テトラリン、クロロベンゼン、トルエン、キシレン、アニソール、メシチレン、テトラロン、及びこれらの任意の組み合わせを含み、挙げられる。ポリマー電荷移送層溶液は、膜またはフィルターを通して濾過して、220nmよりも大きい粒子を除去し得る。
「ジエノフィル」という用語は、2π−電子を持ち、ディールス・アルダー付加環化反応に関与し得る分子を指す。この例には、アルケン、アルキン、ニトリル、エノールエーテル、及びエナミンが挙げられる。
全ての溶媒及び試薬を商業用供給元、例えば、Sigma−Aldrich,TCI及びAlfa Aesarから得て、可能な限りの最高純度で使用するか、及び/または必要に応じて使用前に再結晶化させた。室内精製/分配システムから乾燥溶媒を得た(ヘキサン、トルエン、及びテトラヒドロフラン)、またはSigma−Aldrichから購入した。「水に敏感な化合物」に関わる全ての実験は、「炉乾燥」ガラス器内で、窒素雰囲気下で、またはグローブボックス内で行われた。
1. 1.N−([1,1’−ビフェニル]−4−イル)−9,9−ジメチル−N−(4−(4,4,5,5−テトラメチル−1,3,2−ジオキサボロラン−2−イル)フェニル)−9H−フルオレン−2−アミン(式1)の合成
モノマーAの化学物質(モノマーA24、657.1mg、0.697mmol)、モノマーBの化学物質(モノマーB4、479.7mg、0.494mmol)、及び1−((ビシクロ[4.2.0]オクタ−1(6),2,4−トリエン−7−イルオキシ)メチル)−3,5−ビス((ビシクロ[4.2.0]オクタ−1,3,5−トリエン−7−イルオキシ)メチル)ベンゼン(C14)(それぞれ10mol%、20mol%、及び40mol%、99.6%の純度)の混合物を、1.2mLの電子アニソールに溶解させて、10重量%の溶液を作製した。上述の溶液のB段階化を、窒素雰囲気下、105℃で5時間かけて行った。室温への冷却後、B段階HTL溶液を電子溶媒で4重量%に希釈した。次いで、等量の電子メタノールをB段階HTL溶液に添加して、HTLポリマーを溶液から沈殿させた。次いで、B段階HTLポリマーを濾過によって収集し、40℃の真空炉内で一晩乾燥させた。結果として生じるB段階HTLポリマーを、電子アニソール中に再溶解させて、4重量%の溶液を作製し、上述の沈殿をもう一度繰り返して、残余HTLモノマーを完全に除去した。最後に、0.71g(77%の収率)のB段階HTLポリマー生成物を、黄色結晶様固体の形態で収集した。表1は、沈殿後のB段階HTLポリマー分子量及び分布を示した。
酸化インジウムスズ(ITO)ガラス基板(2*2cm)を、溶媒水、アセトン、及びイソプロパノールで連続して洗浄し、次いで、UVオゾン洗浄剤で20分間処理した。Plextronics Companyからの正孔注入層(HIL)材料Plexcore(商標)OC AQ−1200は、グローブボックス内で水溶液からITO基板にスピンコーティングし、150℃で20分間焼鈍した。その後、比較蒸発性HTL、N−([1,1’−ビフェニル]−4−イル)−9,9−ジメチル−N−(4−(9−フェニル−9H−カルバゾール−3−イル)フェニル)−9H−フルオレン−2−アミンについては、基板を、HTLの堆積のために熱蒸発器に移した。溶液プロセスのための本発明のHTL、アニソール溶液からHTL材料(B段階HTLポリマー)を堆積させ、150℃で10分間焼鈍して、有機溶媒を除去した。その後、B段階材料の架橋を、205℃で10分間、グローブボックス内のホットプレート上で行った。
装置A:ITO/AQ−1200/比較HTL(蒸発、400Å)/Al;
装置B:ITO/AQ−1200/B段階HTL(架橋せず、390Å)/Al;
装置C:ITO/AQ−1200/B段階HTL(架橋、390Å)/Al;
HODに対する電流−電圧(J−V)特性評価は、Keithley(商標)2400 Sourcemeterで実施した。
Claims (9)
- 重合単位として、モノマーA及びモノマーC架橋剤を含む、ポリマーを含む、組成物から形成される、ポリマー電荷移送層であって、モノマーAが、下記A13〜A28から選択され、
- 前記ポリマーが、下記B1〜B6から選択されるモノマーBをさらに含む、請求項1に記載のポリマー電荷移送層。
- モノマーC架橋剤が、モノマーAの総モルに基づいて、0.1〜50モル%である、請求項1に記載のポリマー電荷移送層。
- モノマーA対モノマーBのモル比が、0.8〜1.2である、請求項2に記載のポリマー電荷移送層。
- モノマーA、モノマーB、及びモノマーCのうちのいずれかが、500g/モル〜28000g/モルの分子量を有する、請求項2に記載のポリマー電荷移送層。
- モノマーA及びモノマーCのうちのいずれかが、99%以上の純度を有する、請求項1に記載のポリマー電荷移送層。
- モノマーA、モノマーB、及びモノマーCのうちのいずれかが、99%以上の純度を有する、請求項2に記載のポリマー電荷移送層。
- 請求項1〜7のいずれか1項に記載のポリマー電荷移送層を備える、有機発光装置。
- 請求項1〜7のいずれか1項に記載のポリマー電荷移送層を備える、有機電子装置。
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PCT/CN2015/070354 WO2016026265A1 (en) | 2014-08-21 | 2015-01-08 | Polymeric charge transfer layer and organic electronic device containing the same |
CNPCT/CN2015/070354 | 2015-01-08 | ||
PCT/CN2015/092893 WO2016110140A1 (en) | 2015-01-08 | 2015-10-27 | Polymeric charge transfer layer and organic electronic device containing same |
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US (1) | US20220069225A1 (ja) |
EP (1) | EP3243226A4 (ja) |
JP (1) | JP6649955B2 (ja) |
CN (1) | CN107112438B (ja) |
TW (1) | TWI689493B (ja) |
WO (1) | WO2016110140A1 (ja) |
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KR102251403B1 (ko) | 2014-11-20 | 2021-05-11 | 주식회사 엘지화학 | 정공수송물질 |
JP2019501872A (ja) * | 2015-11-05 | 2019-01-24 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company | 架橋性正孔輸送材料 |
CN115260456B (zh) * | 2021-04-29 | 2024-06-04 | 财团法人工业技术研究院 | 量子点组合物及发光装置 |
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EP1279689B1 (en) * | 2001-07-25 | 2008-10-01 | MERCK PATENT GmbH | Mono-, Oligo and Poly-3-(1,1-difluoroalkyl)thiophenes and their use as charge transport materials |
WO2005049548A1 (en) * | 2003-11-17 | 2005-06-02 | Sumitomo Chemical Company, Limited | Crosslinkable substituted fluorene compounds |
TW201219350A (en) * | 2003-11-17 | 2012-05-16 | Sumitomo Chemical Co | Crosslinkable arylamine compounds |
EP2067805B1 (en) * | 2006-09-25 | 2014-12-17 | Sumitomo Chemical Company, Limited | Polymer compound and polymer light-emitting device using the same |
JP5625271B2 (ja) * | 2008-07-29 | 2014-11-19 | 住友化学株式会社 | 高分子化合物及びそれを用いた発光素子 |
JP5699684B2 (ja) * | 2011-02-25 | 2015-04-15 | 三菱化学株式会社 | 重合体、有機電界発光素子材料、有機電界発光素子用組成物、有機電界発光素子、有機el表示装置及び有機el照明 |
US9562136B2 (en) * | 2011-07-04 | 2017-02-07 | Cambridge Display Technology, Ltd. | Polymers, monomers and methods of forming polymers |
CN103044661A (zh) * | 2011-10-11 | 2013-04-17 | 中国科学院化学研究所 | 芳酰亚胺共轭聚合物、其制备方法及其在有机光电子器件中的应用 |
GB2509718A (en) * | 2013-01-09 | 2014-07-16 | Cambridge Display Tech Ltd | Method for forming a layer of an electronic device and appropriate precursor compounds |
EP3413370B1 (en) * | 2014-08-21 | 2019-09-25 | Dow Global Technologies LLC | Oxygen substituted benzoclobutenes derived compositions for electronic devices |
EP3183761A4 (en) * | 2014-08-21 | 2018-04-25 | Dow Global Technologies LLC | Polymeric charge transfer layer and organic electronic device containing the same |
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- 2015-10-27 JP JP2017535365A patent/JP6649955B2/ja not_active Expired - Fee Related
- 2015-10-27 CN CN201580069908.0A patent/CN107112438B/zh not_active Expired - Fee Related
- 2015-10-27 WO PCT/CN2015/092893 patent/WO2016110140A1/en active Application Filing
- 2015-10-27 US US15/541,548 patent/US20220069225A1/en not_active Abandoned
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US20220069225A1 (en) | 2022-03-03 |
JP2018504484A (ja) | 2018-02-15 |
TW201625529A (zh) | 2016-07-16 |
TWI689493B (zh) | 2020-04-01 |
CN107112438A (zh) | 2017-08-29 |
EP3243226A4 (en) | 2018-08-15 |
EP3243226A1 (en) | 2017-11-15 |
WO2016110140A1 (en) | 2016-07-14 |
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