JP5683104B2 - ドープされた有機半導体材料の製造方法及びそのために用いられる配合物 - Google Patents
ドープされた有機半導体材料の製造方法及びそのために用いられる配合物 Download PDFInfo
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- JP5683104B2 JP5683104B2 JP2009500772A JP2009500772A JP5683104B2 JP 5683104 B2 JP5683104 B2 JP 5683104B2 JP 2009500772 A JP2009500772 A JP 2009500772A JP 2009500772 A JP2009500772 A JP 2009500772A JP 5683104 B2 JP5683104 B2 JP 5683104B2
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
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- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
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- BOXSCYUXSBYGRD-UHFFFAOYSA-N cyclopenta-1,3-diene;iron(3+) Chemical compound [Fe+3].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 BOXSCYUXSBYGRD-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
- 229910001218 Gallium arsenide Inorganic materials 0.000 description 1
- 0 SC*1[C@](C2)[C@@]2*C1 Chemical compound SC*1[C@](C2)[C@@]2*C1 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- H—ELECTRICITY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
- C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/10—1,2,5-Thiadiazoles; Hydrogenated 1,2,5-thiadiazoles
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
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- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
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- C09K2211/1018—Heterocyclic compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- H10K50/16—Electron transporting layers
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- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Description
105mgのポリ[9,9−ジオクチルフルオレニル−2,7−ジイル]−コ−1,4−ベンゾ−{2,1´−3}チアジアゾール)(YE)の溶液をトルエン7mlに溶解した。
105mgのポリ[9,9−ジオクチルフルオレニル−2,7−ジイル]−コ−1,4−ベンゾ−{2,1´−3}チアジアゾール)(YE)の溶液をトルエン7mlに溶解した。YEとNdopとの混合物を調製するために、前記溶液2mlに、3mgのNdopを添加した。
10mgのポリ[9,9−ジオクチルフルオレニル−2,7−ジイル]−コ−1,4−ベンゾ−{2,1´−3}チアジアゾール)(YE)の溶液をトルエン1mlに溶解した。10c,10c´−ビ(8,9−ジメチル−2,3,5,6−テトラヒドロ−1H,4H−3a,6a,10b−トリアザ−フルオランテニル)(ダイマー)溶液を、10mgのダイマーを、1mlのトルエンに溶解することにより調製した。1mlのYE−溶液と100μlのダイマー−溶液とを混合することにより、YE:ダイマーの混合溶液を調製した。
105mgのポリ[9,9−ジオクチルフルオレニル−2,7−ジイル]−コ−1,4−ベンゾ−{2,1´−3}チアジアゾール)(YE)の溶液をトルエン7mlに溶解した。10c,10c´−ビ(8,9−ジメチル−2,3,5,6−テトラヒドロ−1H,4H−3a,6a,10b−トリアザ−フルオランテニル)(ダイマー)溶液を、15mgのダイマーを、1mlのトルエンに溶解することにより調製した。1mlのYE−溶液と100μlのダイマー−溶液とを混合することにより、YE:ダイマーの混合溶液を調製した。スピンオン法により、混合溶液からフィルムを製造した。すべての工程は、制限的な光条件の下で行われた。
例3と同様の条件でフィルムを製造した。製造後のフィルムを、光の不存在下、10分間周囲空気に暴露した。その後、サンプルを真空槽に導入し、白色光に暴露した。暴露後1.4nAの電流が測定された。
Claims (13)
- (i)少なくとも1のドーパント前駆体、少なくとも1のドープされる有機材料、及び、溶媒を含む、溶液又は懸濁液を調製する工程と、
(ii)前記溶液又は懸濁液を、基板上に塗布し、溶媒を除去する工程と、
(iii)活性化エネルギーを加えることにより、ドーパント前駆体をドーパントに変換する工程と、を含み、
前記ドーパント前駆体は、前記ドーパントのダイマー、前記ドーパントのオリゴマー、前記ドーパントのジスピロ化合物、又は、前記ドーパントの多環式化合物であり、活性化エネルギーを加えることにより前記ドーパントに分解し、
工程(i)および工程(ii)は、前記ドーパント前駆体を前記ドーパントに変換するために必要な活性化エネルギーを部分的又は完全に排除して行われる、
ドープされた有機半導体材料の製造方法であって、
前記ドーパントは、以下の構造を有するものからなる群より選択される、ドープされた有機半導体材料の製造方法:
構造5において、A1及びA2は、一方のみ又は両方存在し、前記と同様に定義され、Tは、CR22、CR22R23、N、NR21、O及びSからなる群より選択され;
構造7は、Z、Z1及びZ2からなる群より選択される1又は1より多い架橋結合であり、Z、Z1及びZ2は独立して、アルキル、アルケニル、アルキニル、シクロアルキル、シリリル、アルキルシリリル、ジアゾ、ジスルフィド、ヘテロシクロアルキル、ヘテロシクリル、ピペラジニル、ジアルキルエーテル、ポリエーテル、第一アルキルアミン、アリールアミン及びポリアミン、アリール及びヘテロアリールから選択され;
X及びYは独立して、O、S、N、NR21、P及びPR21からなる群より選択され;
R0−18、R21、R22及びR23は、独立して、置換された又はされない、アリール、ヘテロアリール、ヘテロシクリル、ジアリールアミン、ジヘテロアリールアミン、ジアルキルアミン、ヘテロアリールアルキルアミン、アリールアルキルアミン、H、F、シクロアルキル、ハロゲンシクロアルキル、ヘテロシクロアルキル、アルキル、アルケニル、アルキニル、トリアルキルシリル、トリアリールシリル、ハロゲン、スチリル、アルコキシ、アリーロキシ、チオアルコキシ、チオアリーロキシ、シリリル、及び、トリアルキルシリルアルキニルから選択され、又は、R0−18、R21、R22及びR23は、単独又は組み合わせて、環構造、(ヘテロ)脂肪族化合物、又は、(ヘテロ)芳香族化合物の部分である。 - 工程(iii)の活性化は、光エネルギーによることを特徴とする請求項1に記載の製造方法。
- 前記ドープされる有機材料及びドーパント前駆体は、帯電していない状態で用いられることを特徴とする請求項1又は2に記載の製造方法。
- 工程(ii)では、フィルムが基板上に形成されることを特徴とする請求項1〜3のいずれか1項に記載の製造方法。
- 前記フィルムは、スピンコーティング、ディップコーティング、又は、インクジェット式印刷を含む印刷技術により形成されることを特徴とする請求項4に記載の製造方法。
- 前記工程(iii)では、ドーパント前駆体は不可逆的に分解することを特徴とする請求項1〜5のいずれか1項に記載の製造方法。
- 前記ドーパント前駆体は、エネルギーを加えることにより分解するドナー様の部分のみからなることを特徴とする請求項1〜6のいずれか1項に記載の製造方法。
- 前記溶媒は、トルエン、テトラクロロメタン、ベンゼン、塩化メチレン、クロロホルム、及び、テトラヒドロフランから選択されることを特徴とする請求項1〜7のいずれか1項に記載の製造方法。
- 前記ドープされる有機材料は、典型金属元素のキノリナト錯体、フタロシアニン錯体、ポルフィリン錯体、フェナントロリン、オキサジアゾール、複素環式芳香族化合物、及び、これらの混合物から選択されることを特徴とする請求項1〜8のいずれか1項に記載の製造方法。
- 前記複素環式芳香族化合物は、N含有複素環式芳香族化合物であることを特徴とする請求項9に記載の製造方法。
- 前記ドープされる有機材料は、共役したポリマー、コポリマー、又は、オリゴマー、或いは、電荷移動機能を有する側鎖型ポリマーであることを特徴とする請求項1〜10のいずれか1項に記載の製造方法。
- 前記基板は、フレキシブル基板、ガラス基板、金属基板、ポリマーフィルム、及び、無機半導体から選択されることを特徴とする請求項1〜11のいずれか1項に記載の製造方法。
- 工程(i)及び(ii)を、ドーパント前駆体のドーパントへの変換に必要な活性化エネルギーの排除下で行うことを特徴とする請求項1〜12のいずれか1項に記載の製造方法。
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EP06005687A EP1837926B1 (de) | 2006-03-21 | 2006-03-21 | Heterocyclisches Radikal oder Diradikal, deren Dimere, Oligomere, Polymere, Dispiroverbindungen und Polycyclen, deren Verwendung, organisches halbleitendes Material sowie elektronisches Bauelement |
EP06005687.6 | 2006-03-21 | ||
EP06005834.4 | 2006-03-22 | ||
EP06005834A EP1837927A1 (de) | 2006-03-22 | 2006-03-22 | Verwendung von heterocyclischen Radikalen zur Dotierung von organischen Halbleitern |
PCT/EP2007/002510 WO2007107356A1 (en) | 2006-03-21 | 2007-03-21 | Method for preparing doped organic semiconductor materials and formulation utilized therein |
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JP2007075684A Active JP4652365B2 (ja) | 2006-03-21 | 2007-03-22 | マトリックス材料とドーピング材料とからなる混合物、及び、ドーピングされた有機材料からなる層の製造方法 |
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Families Citing this family (48)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007107356A1 (en) * | 2006-03-21 | 2007-09-27 | Novaled Ag | Method for preparing doped organic semiconductor materials and formulation utilized therein |
EP2009014B1 (de) * | 2007-06-22 | 2018-10-24 | Novaled GmbH | Verwendung eines Precursors eines n-Dotanden zur Dotierung eines organischen halbleitenden Materials, Precursor und elektronisches oder optoelektronisches Bauelement |
DE102008011185A1 (de) | 2008-02-27 | 2009-09-03 | Osram Opto Semiconductors Gmbh | Verfahren zur Herstellung einer dotierten organischen halbleitenden Schicht |
GB2467316B (en) | 2009-01-28 | 2014-04-09 | Pragmatic Printing Ltd | Electronic devices, circuits and their manufacture |
GB2473200B (en) | 2009-09-02 | 2014-03-05 | Pragmatic Printing Ltd | Structures comprising planar electronic devices |
JP2012195054A (ja) | 2011-03-14 | 2012-10-11 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
WO2012168358A1 (en) * | 2011-06-09 | 2012-12-13 | Novaled Ag | Compound for organic electronic device |
DE102012205945A1 (de) | 2012-04-12 | 2013-10-17 | Siemens Aktiengesellschaft | Organische Superdonoren mit mindestens zwei gekoppelten Carben-Gruppen und deren Verwendung als n-Dotierstoffe |
DE102015200699A1 (de) * | 2015-01-19 | 2016-07-21 | Siemens Aktiengesellschaft | Aminophosphazen-Basen als n-Dotierstoffe in der organischen Elektronik |
GB2544768A (en) * | 2015-11-25 | 2017-05-31 | Cambridge Display Tech Ltd | Charge transfer salt, electronic device and method of forming the same |
EP3208863B1 (en) | 2016-02-22 | 2019-10-23 | Novaled GmbH | Charge transporting semi-conducting material and electronic device comprising it |
JP6224758B2 (ja) | 2016-03-29 | 2017-11-01 | 住友化学株式会社 | 発光素子及びその製造方法 |
JP6851725B2 (ja) | 2016-03-29 | 2021-03-31 | 住友化学株式会社 | 新規化合物及びその製造方法 |
EP3312896B1 (en) | 2016-10-24 | 2021-03-31 | Novaled GmbH | Organic electroluminescent device comprising a redox-doped electron transport layer and an auxiliary electron transport layer |
EP3312899B1 (en) | 2016-10-24 | 2021-04-07 | Novaled GmbH | Electron transport layer stack for an organic light-emitting diode |
EP3312895B1 (en) | 2016-10-24 | 2021-07-28 | Novaled GmbH | Organic semiconducting material comprising an electrical n-dopant and an electron transport matrix and electronic device comprising the semiconducting material |
EP4164358A1 (en) | 2017-01-30 | 2023-04-12 | Novaled GmbH | Electroluminescent device comprising a defined layer arrangement comprising a light emitting layer, a hole transport layer and an electron transport layer |
EP3369729B1 (en) | 2017-03-02 | 2022-01-12 | Novaled GmbH | Fused 9-phenyl-acridine derivatives for use in an electronic device and display device |
DE102017111137A1 (de) | 2017-05-22 | 2018-11-22 | Novaled Gmbh | Organische elektrolumineszente Vorrichtung |
EP3406752B1 (en) | 2017-05-22 | 2023-11-08 | Novaled GmbH | Method for preparing an electronic device |
EP3406599B1 (en) | 2017-05-23 | 2023-02-22 | Novaled GmbH | Organic electronic device comprising an organic semiconductor layer |
EP3407401A1 (en) | 2017-05-23 | 2018-11-28 | Novaled GmbH | Organic electronic device comprising an organic semiconductor layer and a device |
EP3470398B1 (en) | 2017-10-13 | 2022-05-04 | Novaled GmbH | Organic electronic device comprising an organic semiconductor layer |
EP3470412B1 (en) | 2017-10-13 | 2020-07-22 | Novaled GmbH | Organic electronic device comprising an organic semiconductor layer |
EP3483154A1 (en) | 2017-11-09 | 2019-05-15 | Novaled GmbH | Compounds comprising triazine, fluorene and aryl groups and their use in organic electronic devices |
EP3483153A1 (en) | 2017-11-09 | 2019-05-15 | Novaled GmbH | Compounds comprising triazine group, fluorene-group and aryl group and their use in organic electronic devices |
EP3524593B1 (en) | 2018-02-07 | 2023-04-12 | Novaled GmbH | Organic material for an electronic optoelectronic device and electronic device comprising the organic material |
EP3533788A1 (en) | 2018-02-28 | 2019-09-04 | Novaled GmbH | Organic material for an electronic optoelectronic device and electronic device comprising the organic material |
EP3582280B1 (en) | 2018-06-14 | 2024-03-20 | Novaled GmbH | Organic material for an electronic optoelectronic device and electronic device comprising the organic material |
DE102018125307A1 (de) | 2018-10-12 | 2020-04-16 | Novaled Gmbh | Organische lichtemittierende Vorrichtung |
EP3742513A1 (en) | 2019-05-21 | 2020-11-25 | Novaled GmbH | Organic light emitting diode |
EP3840080A1 (en) | 2019-12-17 | 2021-06-23 | Novaled GmbH | Organic electronic device and display device comprising the organic electronic device |
EP4165694A1 (en) | 2020-06-12 | 2023-04-19 | Novaled GmbH | Organic light emitting diode and device comprising the same |
EP3923364A1 (en) | 2020-06-12 | 2021-12-15 | Novaled GmbH | Organic light emitting diode and device comprising the same |
EP4141979A1 (en) | 2021-08-24 | 2023-03-01 | Novaled GmbH | Organic light emitting diode and a compound for use therein |
EP4156314A1 (en) | 2021-09-27 | 2023-03-29 | Novaled GmbH | Organic electronic device and a compound |
EP4177978A1 (en) | 2021-11-05 | 2023-05-10 | Novaled GmbH | Organic light emitting diode, a display device comprising the same and a lighting device comprising the same |
CN117343078A (zh) | 2021-11-25 | 2024-01-05 | 北京夏禾科技有限公司 | 有机电致发光材料和器件 |
EP4198026A1 (en) | 2021-12-14 | 2023-06-21 | Novaled GmbH | Compounds for use in semiconductiong materials suitable for electronic devices |
EP4199125A1 (en) | 2021-12-14 | 2023-06-21 | Novaled GmbH | Organic light emitting diode, method for preparing the same and device comprising the same |
EP4198103A1 (en) | 2021-12-14 | 2023-06-21 | Novaled GmbH | Organic light emitting diode and device comprising the same |
EP4199133A1 (en) | 2021-12-20 | 2023-06-21 | Novaled GmbH | Organic light emitting diode, display device comprising the same, and compound |
EP4273947A1 (en) | 2022-05-02 | 2023-11-08 | Novaled GmbH | Organic light emitting diode and device comprising the same |
EP4273948A1 (en) | 2022-05-02 | 2023-11-08 | Novaled GmbH | Organic light emitting diode and device comprising the same |
EP4299573A1 (en) | 2022-06-30 | 2024-01-03 | Novaled GmbH | Compound, organic semiconducting material comprising the same, organic electronic device comprising the same and a method for preparing the organic electronic device |
EP4321511A1 (en) | 2022-08-09 | 2024-02-14 | Novaled GmbH | Compound, organic semiconducting material comprising the same, organic electronic device comprising the same and display device comprising the same |
EP4346357A1 (en) | 2022-09-29 | 2024-04-03 | Novaled GmbH | Semiconducting material, process for preparing a layer of the semiconducting material, organic semiconducting device comprising the organic semiconducting material, display device comprising the organic semiconducting device and compound |
EP4346356A1 (en) | 2022-09-29 | 2024-04-03 | Novaled GmbH | Semiconducting material, process for preparing a layer of the semiconducting material, organic semiconducting device comprising the semiconducting material and compound |
Family Cites Families (52)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3644770A (en) | 1968-01-18 | 1972-02-22 | Varian Associates | Photoemitter having a p-type semiconductive substrate overlaid with cesium and n-type cesium oxide layers |
US3673011A (en) | 1970-11-02 | 1972-06-27 | Westinghouse Electric Corp | Process for producing a cesium coated gallium arsenide photocathode |
GB1419099A (en) | 1972-08-11 | 1975-12-24 | Thorn Electrical Ind Ltd | Manufacturing electric devices having sealed envelopes |
US6746770B1 (en) * | 1989-05-26 | 2004-06-08 | Internatonal Business Machines Corporation | Electrically conductive and abrasion/scratch resistant polymeric materials, method of fabrication thereof and uses thereof |
US5198153A (en) * | 1989-05-26 | 1993-03-30 | International Business Machines Corporation | Electrically conductive polymeric |
US5315129A (en) | 1990-08-20 | 1994-05-24 | University Of Southern California | Organic optoelectronic devices and methods |
US5093698A (en) | 1991-02-12 | 1992-03-03 | Kabushiki Kaisha Toshiba | Organic electroluminescent device |
JP3256361B2 (ja) | 1993-12-29 | 2002-02-12 | 昭和電工株式会社 | ポリ(アルキル置換−2,5−ピリミジンジイル)及びその製造方法 |
AU5893596A (en) * | 1995-06-02 | 1996-12-18 | Forskningscenter Riso | Novel physically functional materials |
US5811833A (en) * | 1996-12-23 | 1998-09-22 | University Of So. Ca | Electron transporting and light emitting layers based on organic free radicals |
WO1998029388A1 (fr) * | 1996-12-30 | 1998-07-09 | Hydro-Quebec | Sels d'amides perfluores, et leurs utilisations comme materiaux a conduction ionique |
US6312836B1 (en) | 1998-04-10 | 2001-11-06 | The Trustees Of Princeton University | Color-tunable organic light emitting devices |
US6287712B1 (en) | 1998-04-10 | 2001-09-11 | The Trustees Of Princeton University | Color-tunable organic light emitting devices |
JP3370011B2 (ja) | 1998-05-19 | 2003-01-27 | 三洋電機株式会社 | 有機エレクトロルミネッセンス素子 |
US6451415B1 (en) | 1998-08-19 | 2002-09-17 | The Trustees Of Princeton University | Organic photosensitive optoelectronic device with an exciton blocking layer |
GB9826405D0 (en) * | 1998-12-02 | 1999-01-27 | South Bank Univ Entpr Ltd | Method for forming films or layers |
EP1432051B1 (en) * | 1999-04-06 | 2008-10-08 | Cambridge Display Technology Limited | Method for doping a polymer |
TW465119B (en) | 1999-07-23 | 2001-11-21 | Semiconductor Energy Lab | EL display device and a method of manufacturing the same |
US7525165B2 (en) | 2000-04-17 | 2009-04-28 | Semiconductor Energy Laboratory Co., Ltd. | Light emitting device and manufacturing method thereof |
JP2001319698A (ja) | 2000-05-11 | 2001-11-16 | Fuji Photo Film Co Ltd | 光電変換素子および光電池 |
TW593622B (en) | 2000-05-19 | 2004-06-21 | Eastman Kodak Co | Method of using predoped materials for making an organic light-emitting device |
US6809333B2 (en) | 2000-12-25 | 2004-10-26 | Samsung Sdi Co., Ltd. | Organic electroluminescence element |
DE10116876B4 (de) * | 2001-04-04 | 2004-09-23 | Infineon Technologies Ag | Verfahren zur Dotierung elektrisch leitfähiger organischer Verbindungen, organischer Feldeffekttransistor sowie Verfahren zu dessen Herstellung |
ITMI20010995A1 (it) | 2001-05-15 | 2002-11-15 | Getters Spa | Dispensatori di cesio e processo per il loro uso |
TWI262034B (en) | 2002-02-05 | 2006-09-11 | Semiconductor Energy Lab | Manufacturing system, manufacturing method, method of operating a manufacturing apparatus, and light emitting device |
DE10207859A1 (de) | 2002-02-20 | 2003-09-04 | Univ Dresden Tech | Dotiertes organisches Halbleitermaterial sowie Verfahren zu dessen Herstellung |
US6806491B2 (en) | 2002-04-03 | 2004-10-19 | Tsinghua University | Organic light-emitting devices |
WO2003088271A1 (en) | 2002-04-08 | 2003-10-23 | The University Of Southern California | Doped organic carrier transport materials |
AU2003230308A1 (en) | 2002-05-07 | 2003-11-11 | Lg Chem, Ltd. | New organic compounds for electroluminescence and organic electroluminescent devices using the same |
US6719936B2 (en) | 2002-08-23 | 2004-04-13 | Eastman Kodak Company | Method of making a solid compacted pellet of organic material for vacuum deposition of OLED displays |
ITMI20021904A1 (it) | 2002-09-06 | 2004-03-07 | Getters Spa | Elemento accessorio per dispensatori di metalli alcalini |
DE10262143B4 (de) | 2002-12-20 | 2011-01-20 | Ksg Leiterplatten Gmbh | Lichtemittierende Anordnung |
WO2004070787A2 (en) | 2003-02-03 | 2004-08-19 | The Regents Of The University Of California | Method for making multifunctional organic thin films |
US7238383B2 (en) | 2003-03-07 | 2007-07-03 | Eastman Kodak Company | Making and using compacted pellets for OLED displays |
AU2003220906A1 (en) | 2003-03-13 | 2004-09-30 | Fujitsu Limited | Organic electroluminescence device and organic electroluminescence display |
US6837939B1 (en) | 2003-07-22 | 2005-01-04 | Eastman Kodak Company | Thermal physical vapor deposition source using pellets of organic material for making OLED displays |
US20050023974A1 (en) * | 2003-08-01 | 2005-02-03 | Universal Display Corporation | Protected organic electronic devices and methods for making the same |
DE10338406A1 (de) * | 2003-08-18 | 2005-03-24 | Novaled Gmbh | Dotierte organische Halbleitermaterialien sowie Verfahren zu deren Herstellung |
DE10339772B4 (de) * | 2003-08-27 | 2006-07-13 | Novaled Gmbh | Licht emittierendes Bauelement und Verfahren zu seiner Herstellung |
US7655961B2 (en) | 2003-10-02 | 2010-02-02 | Maxdem Incorporated | Organic diodes and materials |
US6818329B1 (en) | 2003-10-03 | 2004-11-16 | Eastman Kodak Company | Organic electroluminescent devices having a metal sub-layer within a hole-transporting region |
DE10347856B8 (de) | 2003-10-10 | 2006-10-19 | Colorado State University Research Foundation, Fort Collins | Halbleiterdotierung |
DE10357044A1 (de) | 2003-12-04 | 2005-07-14 | Novaled Gmbh | Verfahren zur Dotierung von organischen Halbleitern mit Chinondiiminderivaten |
DE102004010954A1 (de) * | 2004-03-03 | 2005-10-06 | Novaled Gmbh | Verwendung eines Metallkomplexes als n-Dotand für ein organisches halbleitendes Matrixmaterial, organisches Halbleitermaterial und elektronisches Bauteil |
KR20050107238A (ko) | 2004-05-08 | 2005-11-11 | 서동학 | 유기물 및 고분자 소재를 이용한 비휘발성 메모리 소자 |
EP1643568A1 (de) * | 2004-10-04 | 2006-04-05 | Novaled GmbH | Verfahren zum Herstellen einer Schicht aus einem dotierten Halbleitermaterial und Vorrichtung |
EP1648042B1 (en) | 2004-10-07 | 2007-05-02 | Novaled AG | A method for doping a semiconductor material with cesium |
EP1780816B1 (en) | 2005-11-01 | 2020-07-01 | Novaled GmbH | A method for producing an electronic device with a layer structure and an electronic device |
DE502005004425D1 (de) | 2005-12-07 | 2008-07-24 | Novaled Ag | Verfahren zum Abscheiden eines Aufdampfmaterials |
EP1837927A1 (de) * | 2006-03-22 | 2007-09-26 | Novaled AG | Verwendung von heterocyclischen Radikalen zur Dotierung von organischen Halbleitern |
WO2007107356A1 (en) * | 2006-03-21 | 2007-09-27 | Novaled Ag | Method for preparing doped organic semiconductor materials and formulation utilized therein |
ES2310380T3 (es) * | 2006-03-21 | 2009-01-01 | Novaled Ag | Radical o dirradical heterociclicos, sus dimeros, oligomeros, polimeros, compuestos diespiro y policiclos, su utilizacion, material semiconductor organico asi como componente electronico. |
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EP2008318B1 (en) | 2013-02-13 |
JP2007273978A (ja) | 2007-10-18 |
WO2007107356A1 (en) | 2007-09-27 |
TW200739980A (en) | 2007-10-16 |
KR101361710B1 (ko) | 2014-02-10 |
KR20090025188A (ko) | 2009-03-10 |
DE102007014048A1 (de) | 2007-09-27 |
JP4652365B2 (ja) | 2011-03-16 |
US20100233844A1 (en) | 2010-09-16 |
JP2009530836A (ja) | 2009-08-27 |
EP2008318A1 (en) | 2008-12-31 |
US9065055B2 (en) | 2015-06-23 |
TWI353677B (en) | 2011-12-01 |
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