WO2000003565A1 - Matieres moleculaires amorphes pour dispositifs opto-electroniques et procede de production de celles-ci - Google Patents

Matieres moleculaires amorphes pour dispositifs opto-electroniques et procede de production de celles-ci Download PDF

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WO2000003565A1
WO2000003565A1 PCT/US1999/015437 US9915437W WO0003565A1 WO 2000003565 A1 WO2000003565 A1 WO 2000003565A1 US 9915437 W US9915437 W US 9915437W WO 0003565 A1 WO0003565 A1 WO 0003565A1
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organic
light emitting
emitting device
organic light
electrode
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Warren Oldham, Jr.
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FED Corp
eMagin Corp
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    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional [2D] radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional [2D] 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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    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/14—Styryl dyes
    • C09B23/148—Stilbene dyes containing the moiety -C6H5-CH=CH-C6H5
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    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
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    • C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
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    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
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    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/114—Poly-phenylenevinylene; Derivatives thereof
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    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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    • 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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    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • the present invention relates generally to compounds for use in organic light emitting devices (OLEDs). More particularly, the present invention relates to novel highly symmetrical tetrahedral shaped aromatic and/or aromatic amine containing molecules, and their syntheses, for application in high temperature OLED displays.
  • OLED organic light emitting devices
  • Amorphous molecular films are easily fabricated using the thermal deposition method. Variables such as deposition rate and temperature of substrate can be tuned to control film morphology. As a rule, higher deposition rates and cooler substrate temperatures each favor the preparation of amorphous molecular films. Once formed however, most molecular films tend to crystallize at room temperature because the amorphous morphology is generally a non- equilibrium phase, higher in energy than the ordered crystalline (polycrystalline) phase. The rate of film crystallization depends on the ambient temperature and its relation to the glass transition temperature (T g ) of the material. A second important factor controlling film crystallization is maximum crystallization velocity (MCV), which is also characteristic of a particular material.
  • MCV maximum crystallization velocity
  • Stable amorphous films will have a high T g and a low MCV. If the T g value of an amorphous material is greater than its thermal environment, that material will tend to remain amorphous. Similarly, if the MCV is very low. even at high temperatures some materials will remain amorphous indefinitely. It is possible to relate these thermodynamic and kinetic factors to understand how molecular design can be optimized to yield thermally stable amorphous molecular films. From this analysis. Naito has concluded that thermally stable organic dye glasses can be formed form large, symmetric, globular, rigid, and dense molecules, ((a) Naito, K.; Miura, A. J Phys. Chem. 1993 97, 6240-6248.
  • T g of NPB is 95 °C compared to 175 °C for the electron transport material, Alq 3 .
  • An informative report by Tokito, et al. highlights the limiting thermal stability of the hole-conducting layer, ((a)
  • the experiment was carried out by driving each device at a constant current of 11 mA/cm 2 and gradually increasing the ambient temperature from room temperature upwards. For each device, a dramatic drop in electroluminescence output was observed just above the T g of each hole conducting layer. Shown below are the five hole conducting compounds with their T g values and the temperature at which electroluminescence output rapidly degraded.
  • tertiary aromatic amines have been found to function very well as hole conducting materials due to a low ionization potential and good hole mobility.
  • the most simple aromatic amines such as triphenylamine, do not form stable amorphous films.
  • Assembling larger molecules such as in the case of the benzidine compounds (e.g. NPB) can be used to improve the film forming properties.
  • the synthetic strategy that has been followed to further increase glass transition temperatures of these materials links aromatic arnines together to form either "starburst" structures (shown below). (See for example: (a) Shirota, Y.; Kobata,
  • TPPE TPPE
  • the open linear structure allows adjacent molecules to interact over a large portion of their molecular surface and would be expected to have the greatest difficulty in thermal sublimation.
  • Thermal sublimation requires that the weak intermolecular forces holding the molecules in the solid state must be broken to force the molecules in the gas phase.
  • perfectly symmetrical spherical structures should only interact with adjacent molecules at their periphery. In principle, much larger molecular weight materials should be accessible without drastically compromising the compound's volatility.
  • the known "starburst" structures have not utilized central cores that enforce truly spherical geometry.
  • the 1,3,5-substituted benzene ring is trigonal planar and triphenyoamine is trigonal pyramidal.
  • T g glass transition temperature
  • the organic compounds contain tetrahedral shaped core structures allowing the organic light emitting device to operate at
  • the present invention comprises an organic light emitting device comprising a first electrode, a second electrode, and an organic stack interposed between the first electrode and the second electrode, wherein the organic stack further comprises at least one organic layer, wherein the organic layer further comprises organic compounds such that the organic light emitting device continues to function in temperatures in excess of 145° C.
  • the organic layer may be comprised of organic compounds with tetrahedral shaped core structures, tetrahedral shaped core structures containing aromatic side groups, tetrahedral shaped core structures containing aromatic amine side groups, symmetrical tetrahedral shaped core structures, symmetrical tetrahedral shaped core structures containing aromatic side groups, and/or symmetrical tetrahedral shaped core structures containing aromatic amine side groups.
  • the aromatic side groups may be, but are not limited to, phenyl, naphthyl, anthracyl, carbazole, and any and all substituted analogs thereof.
  • the tetrahedral or symmetrical tetrahedral shaped core structure may be a tetraphenyl compound, including, but not limited to, tetraphenylmethane, tetraphenylsilane, tetraphenyladamantane, tetraphenylgermane, tetraphenylplumbane. and/or tetramethylstannane.
  • the tetraphenyl compound may be functionalized at the ⁇ ro-position.
  • the tetrahedral shaped core structures may satisfy one or more of the formula (C 6 H 5 ) 4 R, where R may be, but is not limited to, C, Si, adamantane (C 10 H t2 ), Ge, Pb, or Sn.
  • R may be, but is not limited to, C, Si, adamantane (C 10 H t2 ), Ge, Pb, or Sn.
  • the organic compounds with tetrahedral shaped core structures may satisfy one or more of the formula (C 6 H 5 ) 4 R, where R may be, but is not limited to, C, Si, adamantane (C 10 H t2 ), Ge, Pb, or Sn.
  • the organic compounds with tetrahedral shaped core structures may satisfy one or more of the formula (C 6 H 5 ) 4 R, where R may be, but is not limited to, C, Si, adamantane (C 10 H t2 ), Ge, Pb, or
  • R (C 6 H 5 ) 4 R, where R, may be, but is not limited to, aromatic groups and/or aromatic amine groups, and where R may be, but is not limited to, C, Si, adamantane (C 10 H 12 ), Ge, Pb, or Sn.
  • the tetrahedral shaped core structures may be, but are not limited to:
  • the organic layer may contain, but is not limited to, organic compounds selected from the group consisting of:
  • R may be, but is not limited to, the group consisting of:
  • the organic compounds with a tetraphenyl core may be, but are not limited to, the group consisting of:
  • the tetraphenyl core may be, but is not limeted to. tetraphenylmethane. tetraphenylsilane, tetraphenyladamantane, tetraphenylgermane, tetraphenylplumbane, and/or tetramethylstannane.
  • the present invention comprises an organic light emitting device having a first electrode, a second electrode, and an organic stack interposed between the first electrode and the second electrode, where the organic stack may further comprise at least one hole transport layer.
  • the hole transport layer may further comprise organic compounds with tetrahedral shaped core
  • the organic compounds of the at least one hole transport layer may be comprised of tetrahedral shaped core structures, tetrahedral shaped core structures containing aromatic side groups, tetrahedral shaped core structures containing aromatic amine side groups, symmetrical tetrahedral shaped core structures, symmetrical tetrahedral shaped core structures containing aromatic side groups, and/or symmetrical tetrahedral shaped core structures containing aromatic amine side groups.
  • the aromatic side groups may be, but are not limited to, phenyl, naphthyl, anthracyl, carbazole. and any and all substituted analogs thereof.
  • the tetrahedral or symmetrical tetrahedral shaped core structure may be a tetraphenyl compound, including, but not limited to, tetraphenylmethane, tetraphenylsilane, tetraphenyladamantane, tetraphenylgermane, tetraphenylplumbane, and/or tetramethylstannane.
  • the tetraphenyl compound may be functionalized at the ⁇ ra-position.
  • the organic layer of the present invention may further comprise organic compounds containing tetrahedral shaped core structures including, but not limited to, silicon based tetrahedral core structures, carbon based tetrahedral core structures, adamantane based tetrahedral core structures, germane based tetrahedral core structures, plumbane based tetrahedral core structures, and stannane based tetrahedral core structures.
  • the tetrahedral shaped core structures may contain aromatic side groups and/or aromatic amine side groups oriented away from one another at angles between 100° and 120°.
  • the present invention describes novel highly symmetrical tetrahedral shaped aromatic amine containing molecules and their syntheses for application as hole conduction materials in high temperature OLED displays.
  • Applicant has identified tetraphenylmethane, tetraphenylsilane and tetraphenyladamantane as very attractive candidates to serve as rigid tetrahedral core structures.
  • Tetraphenylmethane Tetraphenylsilane Tetraphenyladamantane
  • the tetrahedral core structures shown above are easily obtained in large quantities using developed synthetic methodology, ((a) Wilson, L.M.; Griffin, A.C. J. Mater. Chem. 1993, 3, 991-994. (b) Su, D.; Menger, F.M. Tetrahedron Lett. 1997, 38, 1485-1487. (c) Liu, F.-Q.;
  • the rigid tetrahedral framework orients the appended groups away from one another at an angle of between 100° and 120°, or approximately 109.5°, and reduces the possibility of forming intramolecular ⁇ -stacked compounds. If rigid dye molecules are coupled in the tetrahedral array, the proposed molecular design should discourage undesirable intramolecular aggregate or exciplex formation. Also because the organic dye molecules radiate from a central tetrahedral core, they are hindered from forming intermolecular ⁇ -aggregates in solid state films, thereby preventing luminescence
  • Applicant has also pursued the synthesis of tetrahedral amine-containing materials that are linked to the core via phenyl- henyl or phenyl-vinyl connections to further explore the effect of structural diversity on solid state morphology and thermal stability.
  • the present invention allows a novel entry of a large number of different aromatic amines for use in OLEDs.
  • the variety of aromatic groups such as phenyl and substituted analogs thereof, naphthyl, anthracyl, carbazolyl, etc. provides access to range of possible structures.
  • the approach of the present invention can be used to quickly screen many potential and novel hole transport materials, that will be selected for application based on hole transport properties and T g .
  • the novel materials should maintain the desirable hole transport properties common to aromatic amines, but will significantly extend the required high temperature morphological stability.
  • T g values anticipated for the proposed and novel aromatic amine containing materials may be roughly estimated from related tetrahedral stilbenoid compounds prepared by Oldham, et al. (Oldham, W.J., Jr.; Lachicotte, R.J.; Bazan, G.C. J. Am. Chem. Soc. 1998, 120, (in press).
  • high T g blue luminescent materials were prepared by coupling vinylstilbene derivatives to a tetraphenylmethane core using the palladium catalyzed Heck reaction (eq. 2).
  • the tetrahedral core strategy provides materials with high T g and very low crystallization velocities. Materials of this class can be fabricated as amorphous thin-films that are completely stable against crystallization, even when heated above their glass transition temperature.
  • a significant advantage of the tetrahedral core molecular design over polymeric OLED materials is that it combines the traditional advantages of small molecules (e.g. high chemical purity and volatility) with those of polymers (e.g., high T g , low MCV, thermal stability).
  • the hole transport materials proposed in this work are new compounds.
  • An object of the present invention is to successfully prepare and purify the compounds for electronic applications. Although the proposed synthetic methods are developed and have been used successfully in related systems, the compounds of the present invention have not previously been synthesized.
  • Another object of the present invention is to design and synthesize novel high molecular weight materials (expected to have the highest thermal stability), while retaining the volatility necessary to allow films to be fabricated by thermal sublimation. Applicant believes that the new materials containing four amine groups should possess the necessary volatility.
  • the chemical stability of radical cations (also called holes) incorporating the core structures is unknown. Triphenylmethyl cation or triphenylmethyl radical are relatively stable species and the danger of disproportionation reactions upon injection of holes is a primary consideration. To mitigate against this possibility
  • the ionization potential of the new materials could be altered relative to NPB. If the ionization potential is reduced too much, then undesirable exciplex formation can occur at the interface of the hole transport layer and Alq 3 .
  • Another object of the present invention is to control the ionization potential to ameliorate this risk by judicious choice of aromatic groups bonded to nitrogen.
  • tetrahedral shaped core molecules may include carbon, silicon, adamantane. germane, plumlane. or stannane structures or elements.

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un dispositif électroluminescent organique comportant une première électrode, une deuxième électrode, et un empilage organique placé entre la première électrode et la deuxième électrode. L'empilage organique comporte au moins une couche organique. La couche organique comporte des composés organiques permettant au dispositif électroluminescent organique de continuer à fonctionner à des températures dépassant 145 °C. La couche organique peut être constituée de composés organiques possédant des structures à noyau tétraédrique, des structures à noyau tétraédrique contenant des groupes latéraux aromatiques, des structures à noyau tétraédrique contenant des groupes latéraux amines aromatiques, des structures à noyau tétraédrique symétriques, des structures à noyau tétraédrique symétriques contenant des groupes latéraux aromatiques, et/ou des structures à noyau tétraédrique symétriques contenant des groupes latéraux amines aromatiques.
PCT/US1999/015437 1998-07-10 1999-07-09 Matieres moleculaires amorphes pour dispositifs opto-electroniques et procede de production de celles-ci Ceased WO2000003565A1 (fr)

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JP2002083685A (ja) * 2000-06-28 2002-03-22 Matsushita Electric Ind Co Ltd 有機電界発光素子
WO2002043449A1 (fr) * 2000-11-24 2002-05-30 Toray Industries, Inc. Materiau luminescent et element luminescent contenant celui-ci
KR20020046316A (ko) * 2000-12-12 2002-06-21 엘지전자 주식회사 유기전계발광 소자
US6444333B1 (en) * 1998-10-12 2002-09-03 Fuji Photo Film Co., Ltd. Organic luminescent device material, organic luminescent device using the same, and tetraarylmethane compound
WO2003017732A1 (fr) * 2001-08-16 2003-02-27 3M Innovative Properties Company Procede et materiaux permettant de configurer une matrice polymerisable et amorphe recouverte d'un materiau electriquement actif
WO2003017731A1 (fr) * 2001-08-16 2003-02-27 3M Innovative Properties Company Procede et materiaux destines a la formation de motifs sur une matrice organique, non polymere, amorphe, et contenant un materiau electrique
WO2003028125A3 (fr) * 2001-09-27 2003-07-03 3M Innovative Properties Co Semi-conducteur constitue de pentacene substitue
US6777111B1 (en) * 1999-08-04 2004-08-17 Kabushiki Kaisha Chuo Kenkyusho Electro luminescent element
US6824890B2 (en) * 2000-05-03 2004-11-30 The Regents Of The University Of California Soluble tetrahedral compounds for use in electroluminescent devices
US6974877B2 (en) 2001-09-27 2005-12-13 3M Innovative Properties Company Process for preparing pentacene derivatives
WO2007000268A3 (fr) * 2005-06-25 2007-04-19 Univ Darmstadt Tech Oligotetracenes, leur production et leur application
US7241512B2 (en) 2002-04-19 2007-07-10 3M Innovative Properties Company Electroluminescent materials and methods of manufacture and use
WO2007074174A3 (fr) * 2005-12-29 2007-08-16 Univ Rennes Composes fluorescents et utilisation de tels composes dans le cadre de procedes ou dispositifs multiphotoniques
KR100819761B1 (ko) 2006-09-16 2008-04-07 (주)파인켐 테트라키스페닐계 유기발광화합물 및 이를 이용한유기전계발광소자
KR100819760B1 (ko) 2006-11-06 2008-04-07 (주)파인켐 테트라키스페닐계 유기발광화합물 및 이를 이용한유기전계발광소자
CN100452478C (zh) * 2004-05-24 2009-01-14 索尼株式会社 有机电致发光元件以及由此构成的显示装置
US7901594B2 (en) 2000-02-29 2011-03-08 Japan Science And Technology Corporation Polyacene derivatives and production thereof
JP4916078B2 (ja) * 2000-03-27 2012-04-11 出光興産株式会社 有機エレクトロルミネッセンス素子
CN103232483A (zh) * 2013-04-15 2013-08-07 中国科学院化学研究所 二吡咯硼烷类化合物（bodipy）及其制备方法和应用
WO2013182847A1 (fr) * 2012-06-06 2013-12-12 The University Of Warwick Composés organiques accepteurs d'électrons
EP2759585A1 (fr) * 2002-11-26 2014-07-30 Konica Minolta Business Technologies, Inc. Élément électroluminescent organique, affichage et illuminateur
KR20160003589A (ko) * 2015-12-14 2016-01-11 중앙대학교 산학협력단 게르마늄 중심 덴드리머 화합물, 이를 포함하는 유기광전자소자
JP2017034278A (ja) * 2011-07-08 2017-02-09 株式会社半導体エネルギー研究所 発光素子、発光装置、電子機器、照明装置

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US6444333B1 (en) * 1998-10-12 2002-09-03 Fuji Photo Film Co., Ltd. Organic luminescent device material, organic luminescent device using the same, and tetraarylmethane compound
US6777111B1 (en) * 1999-08-04 2004-08-17 Kabushiki Kaisha Chuo Kenkyusho Electro luminescent element
US7901594B2 (en) 2000-02-29 2011-03-08 Japan Science And Technology Corporation Polyacene derivatives and production thereof
EP1205527B2 (fr) † 2000-03-27 2020-10-07 Idemitsu Kosan Co., Ltd. Dispositif a electroluminescence organique
US8753757B2 (en) 2000-03-27 2014-06-17 Idemitsu Kosan Co., Ltd. Organic electroluminescence element
JP4916078B2 (ja) * 2000-03-27 2012-04-11 出光興産株式会社 有機エレクトロルミネッセンス素子
US6824890B2 (en) * 2000-05-03 2004-11-30 The Regents Of The University Of California Soluble tetrahedral compounds for use in electroluminescent devices
JP2002083685A (ja) * 2000-06-28 2002-03-22 Matsushita Electric Ind Co Ltd 有機電界発光素子
US7318966B2 (en) 2000-11-24 2008-01-15 Toray Industries, Inc. Luminescent element material and luminescent element comprising the same
WO2002043449A1 (fr) * 2000-11-24 2002-05-30 Toray Industries, Inc. Materiau luminescent et element luminescent contenant celui-ci
KR100867495B1 (ko) * 2000-11-24 2008-11-06 도레이 가부시끼가이샤 발광 소자 재료 및 이를 이용한 발광 소자
KR20020046316A (ko) * 2000-12-12 2002-06-21 엘지전자 주식회사 유기전계발광 소자
EP1215739A3 (fr) * 2000-12-12 2005-03-16 Lg Electronics Inc. Dispositif organique électroluminescent
WO2003017732A1 (fr) * 2001-08-16 2003-02-27 3M Innovative Properties Company Procede et materiaux permettant de configurer une matrice polymerisable et amorphe recouverte d'un materiau electriquement actif
US7014978B2 (en) 2001-08-16 2006-03-21 3M Innovative Properties Company Method and materials for patterning of an amorphous, non-polymeric, organic matrix with electrically active material disposed therein
US6844128B2 (en) 2001-08-16 2005-01-18 3M Innovative Properties Company Method and materials for patterning of an amorphous, non-polymeric, organic matrix with electrically active material disposed therein
CN100446299C (zh) * 2001-08-16 2008-12-24 3M创新有限公司 在内含电活性材料的无定形非聚合物有机基质上形成图案的方法和材料
US7276322B2 (en) 2001-08-16 2007-10-02 3M Innovative Properties Company Method and materials for patterning of an amorphous, non-polymeric, organic matrix with electrically active material disposed therein
US7977864B2 (en) 2001-08-16 2011-07-12 Samsung Mobile Display Co., Ltd. Method and materials for patterning of an amorphous, non-polymeric, organic matrix with electrically active material disposed therein
WO2003017731A1 (fr) * 2001-08-16 2003-02-27 3M Innovative Properties Company Procede et materiaux destines a la formation de motifs sur une matrice organique, non polymere, amorphe, et contenant un materiau electrique
US6699597B2 (en) 2001-08-16 2004-03-02 3M Innovative Properties Company Method and materials for patterning of an amorphous, non-polymeric, organic matrix with electrically active material disposed therein
US7445825B2 (en) * 2001-08-16 2008-11-04 3M Innovative Properties Company Donor sheet having a polymerizable, amorphous matrix with electrically active material disposed therein
JP2005500652A (ja) * 2001-08-16 2005-01-06 スリーエム イノベイティブ プロパティズ カンパニー 電気活性材料が内部に配置された非晶質非ポリマー有機母材のパターン化方法および材料
US6974877B2 (en) 2001-09-27 2005-12-13 3M Innovative Properties Company Process for preparing pentacene derivatives
US6864396B2 (en) 2001-09-27 2005-03-08 3M Innovative Properties Company Substituted pentacene semiconductors
WO2003028125A3 (fr) * 2001-09-27 2003-07-03 3M Innovative Properties Co Semi-conducteur constitue de pentacene substitue
US7442421B2 (en) 2002-04-19 2008-10-28 3M Innovative Properties Company Electroluminescent materials and methods of manufacture and use
US7241512B2 (en) 2002-04-19 2007-07-10 3M Innovative Properties Company Electroluminescent materials and methods of manufacture and use
EP2759585A1 (fr) * 2002-11-26 2014-07-30 Konica Minolta Business Technologies, Inc. Élément électroluminescent organique, affichage et illuminateur
CN100452478C (zh) * 2004-05-24 2009-01-14 索尼株式会社 有机电致发光元件以及由此构成的显示装置
US8293957B2 (en) 2005-06-25 2012-10-23 Dritte Patentportfolio Beteiligungsgesellschaft Mbh & Co. Kg Oligo-tetracenes, production and use thereof
WO2007000268A3 (fr) * 2005-06-25 2007-04-19 Univ Darmstadt Tech Oligotetracenes, leur production et leur application
WO2007074174A3 (fr) * 2005-12-29 2007-08-16 Univ Rennes Composes fluorescents et utilisation de tels composes dans le cadre de procedes ou dispositifs multiphotoniques
KR100819761B1 (ko) 2006-09-16 2008-04-07 (주)파인켐 테트라키스페닐계 유기발광화합물 및 이를 이용한유기전계발광소자
KR100819760B1 (ko) 2006-11-06 2008-04-07 (주)파인켐 테트라키스페닐계 유기발광화합물 및 이를 이용한유기전계발광소자
JP2017034278A (ja) * 2011-07-08 2017-02-09 株式会社半導体エネルギー研究所 発光素子、発光装置、電子機器、照明装置
WO2013182847A1 (fr) * 2012-06-06 2013-12-12 The University Of Warwick Composés organiques accepteurs d'électrons
CN103232483A (zh) * 2013-04-15 2013-08-07 中国科学院化学研究所 二吡咯硼烷类化合物（bodipy）及其制备方法和应用
KR20160003589A (ko) * 2015-12-14 2016-01-11 중앙대학교 산학협력단 게르마늄 중심 덴드리머 화합물, 이를 포함하는 유기광전자소자
KR101971485B1 (ko) 2015-12-14 2019-04-24 중앙대학교 산학협력단 게르마늄 중심 덴드리머 화합물, 이를 포함하는 유기광전자소자

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