WO2011014039A1 - Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant - Google Patents

Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant Download PDF

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WO2011014039A1
WO2011014039A1 PCT/KR2010/005039 KR2010005039W WO2011014039A1 WO 2011014039 A1 WO2011014039 A1 WO 2011014039A1 KR 2010005039 W KR2010005039 W KR 2010005039W WO 2011014039 A1 WO2011014039 A1 WO 2011014039A1
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organic electroluminescent
subst
substituent
compound
ring
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PCT/KR2010/005039
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English (en)
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Hyo Jung Lee
Young Jun Cho
Sung Jin Eum
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
Seung Soo Yoon
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority claimed from KR1020100064849A external-priority patent/KR20110013220A/ko
Application filed by Rohm And Haas Electronic Materials Korea Ltd. filed Critical Rohm And Haas Electronic Materials Korea Ltd.
Priority to US13/388,244 priority Critical patent/US20120217485A1/en
Priority to CN2010800393763A priority patent/CN102625806A/zh
Publication of WO2011014039A1 publication Critical patent/WO2011014039A1/fr

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    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
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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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Definitions

  • the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same, more particularly, to novel organic electroluminescent compounds used as an electroluminescent material and an organic electroluminescent device using the same as a host .
  • CBP is the most widely known as a host material for a phosphorescent material.
  • the OLED devices do not have satisfactory operation life. Therefore, development of more stable and higher-performance host materials is required.
  • the object of the present invention is to provide organic electroluminescent compounds having the backbone to provide better luminous efficiency and device life with appropriate color coordinate as compared to conventional host or dopant material, while overcoming the problems described above. Another object is to provide a highly efficient and long life organic electroluminescent device using the organic electroluminescent compounds.
  • novel organic electroluminescent compounds represented by Chemical Formula 1 and an organic electroluminescent device using the same. Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property compared to the existing host material, it may be used to manufacture OLED devices having very superior operation life.
  • a aanndd aa ring B represent a 6-membered aromatic ring or a 6- membered hetero aromatic ring;
  • p and r represent an integer from 0 to 2
  • q and s represent an integer from 2 to 4, with the proviso that p+r ⁇ l, p+q ⁇ 4 and r+s ⁇ 4;
  • Li and L 2 independently represent a chemical bond, (C6-C30)arylene with or without substituent(s) , (C3-C30)heteroarylene with or without subst ituent(s) , 5- to 7-membered heterocycloalkylene with or without subst ituent(s) , 5- to 7-membered heterocycloalkylene fused with one or more aromatic ring(s) with or without subst ituent(s) , (C3-C30)cycloalkylene with or without subst ituent(s) , (C3-C30)cycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C2-C30)alkenylene with or without subst ituent(s), (C2-C30)alkynylene with or without subst ituent(s) , (C6-C30)ar(Cl-C30)alkylene with or without subst ituent
  • Ari and Ar2 independently represent hydrogen, halogen, (Cl-C30)alkyl with or without substituent(s) , (C6-C30)aryl with or without substituent(s), substituted or unsubst ituted (C6-C30)aryl fused with one or more (C3- C30)cycloalkyl with or without substituent (s) , (C3-C30)heteroaryl with or without subst ituent(s), 5- to 7-membered heterocycloalkyl with or without subst ituent(s) , 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without subst ituent(s) , (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, -NR11R12, -S1
  • Rn through R 2 o independently represent (Cl-C30)alkyl with or without subst ituent(s), (C6-C30)aryl with or without substituent(s) or (C3- C30)heteroaryl with or without subst ituent(s) or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring;
  • the Xi through X 8 independently represent CR21 or N; except for the case where all of Xi through X 8 are CR21 or N;
  • R21 through R 28 are the same as defined in the Rn through R20, and m represents an integer of 1 or 2;
  • the heterocycloalkyl or heteroaryl may include one or more heteroatom(s) selected from N, 0, S and Si.
  • 'alkyl', 'alkoxy' and other substituents including 'alkyl' moiety include both linear and branched species and 'cycloalkyl' includes monocyclic hydrocarbons as well as polycyclic hydrocarbons such as adamantyl or bicycloalkyl .
  • the term 'aryl' described herein means an organic radical derived from aromatic hydrocarbon via elimination of one hydrogen atom.
  • Each ring includes a monocyclic or fused ring system incuding from 4 to 7, preferably from 5 to 6 cyclic atoms.
  • a structure that one or more aryls are linked by a chemical bond is also included.
  • the aryl include phenyl, naphthyl , biphenyl , anthryl , indenyl, fluorenyl, phenanthryl, triphenylenyl , pyrenyl , perylenyl , chrysenyl , naphthacenyl and fluoranthenyl , but they are not restricted thereto.
  • heteroaryl' described herein means an aryl group including from 1 to 4 heteroatom(s) selected from N, 0 and S for the aromatic cyclic backbone atoms, and cabon atom(s) for remaining aromatic cyclic backbone atoms.
  • the heteroaryl may be a 5- or 6-membered monocyclic heteroaryl or a polycyclic hegeroaryl which is fused with one or more bezene ring(s), and may be partially saturated.
  • the term 'heteroaryl' described herein includes a structure that one or more heteroaryls are linked by a chemical bond.
  • the heteroaryl groups may include divalent aryl groups of which the heteroatoms are oxidized or quarternized to form N-oxides, quaternary salts, or the like.
  • Specific examples of the heteroaryl include monocyclic heteroaryl groups such as furyl , thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl , isothiazolyl , isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl; polycyclic heteroaryl groups such as benzofuryl, benzothienyl , isobenzofuryl , benzimidazolyl , benzothiazolyl , benzisothiazo
  • the '(Cl-C30)alkyl' groups described herein may include (Cl-C20)alkyl or (Cl-ClO)alkyl and the ' (C6-C30)aryl' groups include (C6-C20)aryl or (C6- C12)aryl.
  • the ' (C3-C30)heteroaryl ' groups include (C3-C20)heteroaryl or (C3-C12)heteroaryl and the ' (C3-C30)cycloalkyl ' groups include (C3- C20)cycloalkyl or (C3-C7)cycloalkyl .
  • the ' (C2-C30)alkenyl ' or alkynyl group include (C2-C20)alkenyl or alkynyl, (C2-C10)alkenyl or alkynyl.
  • the substituent is further substituted by one or more substituent(s) independently selected from deuterium, halogen, (Cl-C30)alkyl with or without halogen substituent(s) , (C6-C30)aryl , (C3-C30)heteroaryl with or without (C6-C30)aryl subst ituent(s) , 5- to 7-membered heterocycloalkyl , 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C3- C30)cycloalkyl , (C3-C30)cycl
  • the R 31 through R 37 are independently linked to (Cl-C30)alkyl , (C6- C30)aryl, (C3-C30)heteroaryl or an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring.
  • the Rn through R28 are selected from hydrogen, halogen, alkyl such as methyl, ethyl, propyl, butyl, pentyl , hexyl , ethylhexyl, heptyl , octyl , etc., aryl such as phenyl, naphthyl , fluorenyl, biphenyl, phenanthryl , terphenyl , pyrenyl , perylenyl , spirobifluorenyl , fluoranthenyl , chrysenyl , triphenylenyl , etc., aryl fused with one or more cycloalkyl such as 1,2- dihydroacenaphthyl , heteroaryl such as dibenzothiophenyl , dibenzofuryl , carbazolyl, pyridyl, furyl , thienyl, quinolyl
  • heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxal inyl , phenanthrolinyl, etc., aryloxy such as biphenyloxy, etc., arylthio such as biphenylthio, etc., aralkyl such as biphenylmethyl , triphenylmethyl , etc., carboxyl , nitro, or hydroxyl , but are not limited thereto, and may be further substituted as shown in Chemical Formula 1.
  • organic electroluminescent compound according to the present invention may be exemplified as compounds having following structures represented by Chemical Formulas 2 to 5 but is not limited thereto.
  • organic electroluminescent compound according to the present invention may be exemplified as compounds having following structures but is not limited thereto.
  • Li, L2, Ari, Ar2 and q are the same as defined in Chemical Formula 1, wherein each of the substituents may be different from each other.
  • the Ar 1 and Ar 2 according to the present invention may be exemplified as following structures but are not limited thereto.
  • organic electroluminescent compound according to the present invention may be more specifically exemplified as following compounds but is not limited thereto.
  • an organic electroluminescent device which includes a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer includes one or more organic electroluminescent c ⁇ mpound(s) represented by Chemical Formula 1.
  • the organic electroluminescent compounds are used as host material of an electroluminescent layer.
  • the organic layer includes electroluminescent layer including one or more organic electroluminescent compound(s) represented by Chemical Formula 1 and one or more phosphorescent dopant(s).
  • the electroluminescent dopant applied to the organic electroluminescent device is not specifically limited but may be exemplified as compounds of the following Chemical Formula 6.
  • M is selected from the group consisting of metals of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16, and
  • ligands L , L and L are independently selected from following structures.
  • R2 0 1 through R2 03 independently represent hydrogen, deuterium, (Cl-
  • R204 through R219 independently represent hydrogen, deuterium, (Cl-
  • C30)alkylsilyl with or without subst ituent(s) di(Cl-C30)alkyl(C6- C30)arylsilyl with or without subst ituent(s), tri (C6-C30)arylsi IyI with or without subst ituent (s) , cyano or halogen;
  • R 220 through R22 3 independently represent hydrogen, deuterium, (Cl-
  • R224 and R225 independently represent hydrogen, deuterium, (Cl-C30)alkyl with or without substituent (s), (C6-C30)aryl with or without substituent(s) or halogen, or R224 and R225 are linked via (C3-C12)alkylene or (C3-
  • R226 represents (Cl-C30)alkyl with or without subst ituent(s), (C6-
  • R227 through R 2 29 independently represent hydrogen, deuterium, (Cl- C30)alkyl with or without substituent(s) , (C6-C30)aryl or halogen with or without substituent(s);
  • R 230 and R 2 3 1 independently represent hydrogen, (Cl-C20)alkyl with or without halogen substituent(s), (C6-C20)aryl , halogen, cyano, tri (Cl- C20)alkylsilyl, di(Cl-C20)alkyl(C6-C20)arylsilyl , tri(C6-C20)arylsilyl , (Cl- C20)alkoxy, (Cl-C20)alkylcarbonyl , (C6-C20)arylcarbonyl , di(Cl-C20)alkylamino or di(C6-C20)arylamino, or R230 and R231 are linked via (C3-C12)alkylene or (C3-
  • C12)alkenylene with or without a fused ring may be further substituted with one or more substituent (s) selected from the group consisting of (Cl- C20)alkyl with or without halogen subst ituent(s) , halogen, cyano, tri (Cl- C20)alkylsilyl, di(Cl-C20)alkyl(C6-C20)arylsi IyI , tri(C6-C20)arylsilyl , (Cl- C20)alkoxy, (Cl-C20)alkylcarbonyl , (C6-C20)arylcarbonyl , di(Cl- C20)alkylamino, di(C6-C20)arylamino, phenyl, naphthyl , anthryl, fluorenyl, or spirobifluorenyl , or may be further substituted with phenyl or fluorenyl, which is substituted with one
  • R 232 through R 239 independently represent hydrogen, (Cl-C20)alkyl with or without halogen substituent(s), (Cl-C20)alkoxy, (C3-C12)cycloalkyl , halogen, cyano, (C6-C20)aryl , (C4-C20)heteroaryl , tri (Cl-C20)alkylsi IyI , di (Cl- C20)alkyl(C6-C20)arylsilyl or tri(C6-C20)arylsilyl ;
  • R 2 4i through R252 are linked to an adjacent substituent via alkylene or alkenylene to form a (C5-C7)spiro ring or a (C5-C9)fused ring, or are linked to R207 or R208 via alkylene or alkenylene to form a (C5-C7)fused ring.
  • the M is selected from a group consisting of Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag, and the compounds of Chemical Formula 6 include the examples in KR Patent Application No. 10-2009-0037519, but is not limited thereto.
  • the organic electroluminescent device includes the organic electroluminescent compound of Chemical Formula 1 and includes one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds at the same time.
  • the arylamine compounds and styrylarylamine compounds include the examples in KR Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but are not limited thereto.
  • the organic layer may further include one or more metal (s) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s) as well as the organic electroluminescent compound of Chemical Formula 1.
  • the organic layer may simultaneously include the electroluminescent layer and a charge generating layer.
  • a white light-emitting organic electroluminescent device wherein the organic layer includes one or more organic electroluminescent layer(s) emitting blue, red or green light at the same time as well as the organic electroluminescent compound.
  • the organic electroluminescent compound according to the present invention has good luminescence efficiency and excellent life property compared with the existing host material since it is used as host material of the organic electroluminescent material in the OLED. Accordingly, it may be used to manufacture an OLED having very superior operation life.
  • 1,4-dibromobenzene (15 g, 63.58 mmol) was dissolved in tetrahydrofuran (300 mO and n-butyl lithium (26.7 mL, 2.5M in hexanee, 66.76 mmol) was slowly added thereto at -78 ° C. After the mixture was stirred for 1 hour, solution, in which chlorotriphenylsi lane (20.6 mL) was dissolved in tetrahydrofuran (70 mL), was added thereto and stirred at room temperature for 12 hours. Upon completion of the reaction, the produced white solid was removed by filtering and filtrate was extracted with ethyl acetate.
  • Compound 154 (3.6 g, 5.59 mmol, 44.37 %) was obtained by recrystallization with methanol, ethyl acetate and dimethyl formamide.
  • Compound 156 (5 g, 6.62 mmol, 38.14 %) was obtained by column saparation.
  • diverse compounds represented by Compounds 2 to 5 may be may be combined by introducing diverse substituents according to known combination methods with one or more selected from the group consisting of 2,4-Dichloropyrido[2,3-d]pyrimidine(0Chem Incorporation) , 2-Chloro- pyrido[3,2-d]pyrimidine(Anichem LLC) , pyrido[4,3-d]pyrimidine-4(3H)-one(Aces Pharma, Inc.), 2-Chloro-6,7-dimethyl-pteridine(International Laboratory Limited), 2-Chloropteridine (Princeton BioMolecular Research, Inc.), 3- Chloroquinol ine (Texas Biochemicals Inc.), 2,4-Dichloroquinol ine (Shanghai PI Chemicals Ltd), 2,3-Dichloroquinoline (Aces Pharma, Inc.), 1- Chloroisoquino
  • Organic electroluminescent Compounds 1 to 159 were prepared according to Preparation Examples 1 to 8 and Table 1 shows H NMR and MS/FAB of the prepared organic electroluminescent compounds.
  • An OLED device was manufactured using the electroluminescent material according to the present invention.
  • a transparent electrode ITO thin film (15 ⁇ /D) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
  • an ITO substrate was equipped in a substrate folder of a vacuum vapor deposition apparatus, and 4,4' ,4"-tris(N,N-(2-naphthyl )- phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor
  • NPB N,N'-bis(a-naphthyl)-N,N '-diphenyl-4,4'-diamine
  • An electroluminescent layer was formed on the hole transport layer as follows.
  • the compound according to the present invention e.g., Compound 52
  • an electroluminescent dopant e.g., Compound of (piq) 2 Ir(acac)[bis-(l- phenyl isoquinolyl )iridium(III)acetylacetonate]
  • an electroluminescent dopant e.g., Compound of (piq) 2 Ir(acac)[bis-(l- phenyl isoquinolyl )iridium(III)acetylacetonate]
  • the two materials were evaporated at different speed, so that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 4 to 10 mol%.
  • Table 2 shows the result of driving voltage (V) and luminous efficiency (cd/A) according to Examples.
  • An OLED was manufactured in the same manner as Example 1 except that 4,4'-di(9H-carbazol-9-one)biphenyl (CBP) instead of the organic electroluminescent compound according to the present invention was used as electroluminescent host material in another cell of the vacuum vapor deposition device and Bis(2-methyl-8-quinolinato)(p-phenylphenolato)- aluminum(IIlKBAlq) was used as an electron transport layer.
  • CBP 4,4'-di(9H-carbazol-9-one)biphenyl
  • the organic electroluminescent compounds according to the present invention have excellent luminous properties compared with the conventional material.
  • the device using the organic electroluminescent compound according to the present invention as host material for emitting red color has excellent luminescent efficiency and drops driving voltage, thereby reducing power consumption.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention porte sur de nouveaux composés électroluminescents organiques et sur des dispositifs électroluminescents organiques les utilisant. Etant donné que le composé électroluminescent organique présente un bon rendement lumineux et une excellente caractéristique de durée par comparaison avec le matériau résistant, il peut être utilisé pour fabriquer des dispositifs OLED ayant une durée de vie de fonctionnement supérieure et consommant moins de courant en raison du rendement énergétique amélioré.
PCT/KR2010/005039 2009-07-31 2010-07-30 Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant WO2011014039A1 (fr)

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US13/388,244 US20120217485A1 (en) 2009-07-31 2010-07-30 Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN2010800393763A CN102625806A (zh) 2009-07-31 2010-07-30 新有机电致发光化合物和使用该化合物的有机电致发光设备

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JP2013234183A (ja) * 2012-05-03 2013-11-21 Samsung Display Co Ltd 縮合環化合物及びそれを含んだ有機発光素子
EP2678335A1 (fr) 2011-03-25 2014-01-01 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés pour matériau électronique organique et dispositif électroluminescent organique utilisant un tel matériau
EP2683712A1 (fr) 2011-03-08 2014-01-15 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique utilisant lesdits composés
JP2014522401A (ja) * 2011-05-30 2014-09-04 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機エレクトロニクス材料用の新規化合物およびそれを使用した有機エレクトロルミネッセンス素子
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WO2014185592A1 (fr) * 2013-05-13 2014-11-20 제일모직 주식회사 Composé pour dispositif opto-électrique organique, diode électroluminescente organique comprenant ce composé, et dispositif d'affichage comprenant une telle diode électroluminescente organique
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EP2963038A1 (fr) * 2014-04-29 2016-01-06 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
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EP3359526A4 (fr) * 2015-10-05 2019-04-03 The Trustees of Columbia University in the City of New York Activateurs de flux autophagique et de phospholipase d et clairance d'agrégats de protéines comprenant tau et traitement de protéinopathies
CN110724128A (zh) * 2018-07-16 2020-01-24 哈尔滨工业大学 一种基于1,3-二氮杂萘（喹唑啉）的小分子发光材料及其制备方法与应用
CN115368348A (zh) * 2021-05-18 2022-11-22 江苏三月科技股份有限公司 一种以氰基吡啶为核心的化合物及其应用
US11608344B2 (en) 2020-05-04 2023-03-21 Amgen Inc. Heterocyclic compounds as triggering receptor expressed on myeloid cells 2 agonists and methods of use
US11718617B2 (en) 2020-05-04 2023-08-08 Amgen Inc. Heterocyclic compounds as triggering receptor expressed on myeloid cells2 agonists and methods of use

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EP2616462A1 (fr) 2010-09-17 2013-07-24 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique utilisant celui-ci
EP2683712A1 (fr) 2011-03-08 2014-01-15 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique utilisant lesdits composés
EP2678335A1 (fr) 2011-03-25 2014-01-01 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés pour matériau électronique organique et dispositif électroluminescent organique utilisant un tel matériau
JP2014515738A (ja) * 2011-03-25 2014-07-03 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機電子材料のための新規化合物およびこれを用いた有機電界発光素子
JP2014522401A (ja) * 2011-05-30 2014-09-04 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 有機エレクトロニクス材料用の新規化合物およびそれを使用した有機エレクトロルミネッセンス素子
WO2013154325A1 (fr) * 2012-04-10 2013-10-17 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les contenant
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US9825242B2 (en) 2013-05-13 2017-11-21 Cheil Industries, Inc. Compound for organic optoelectric device, organic light-emitting diode including same, display device including organic light-emitting diode
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