WO2010140801A1 - Nouveaux composés électroluminescents organiques, et dispositif électroluminescent organique utilisant ces composés - Google Patents

Nouveaux composés électroluminescents organiques, et dispositif électroluminescent organique utilisant ces composés Download PDF

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WO2010140801A1
WO2010140801A1 PCT/KR2010/003456 KR2010003456W WO2010140801A1 WO 2010140801 A1 WO2010140801 A1 WO 2010140801A1 KR 2010003456 W KR2010003456 W KR 2010003456W WO 2010140801 A1 WO2010140801 A1 WO 2010140801A1
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alkyl
aryl
heteroaryl
cycloalkyl
tri
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PCT/KR2010/003456
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Seung Soo Yoon
Sung Min Kim
Bong Ok Kim
Hyuck Joo Kwon
Sung Jin Eum
Young Jun Cho
Hyo Jung Lee
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Dow Advanced Display Materials, Ltd.
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Priority to CN2010800349510A priority Critical patent/CN102712663A/zh
Priority to JP2012513864A priority patent/JP5651689B2/ja
Publication of WO2010140801A1 publication Critical patent/WO2010140801A1/fr

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Definitions

  • the present invention relates to a novel organic electroluminescent compound, and an organic electroluminescent device and an organic solar cell including the same. More particularly, the present invention relates to a novel organic electroluminescent compound used as a blue-emitting material and an organic electroluminescent device including the same as a dopant.
  • electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices.
  • Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [ Appl.Phys.Lett. 51,913,1987].
  • the electroluminescent material In an organic EL device, the most important factor that determines its performance including luminescence efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
  • Organic electroluminescent materials may be roughly classified into high-molecular-weight materials and low-molecular-weight materials.
  • the low-molecular-weight materials may be classified into metal complexes and metal-free pure organic electroluminescent materials, depending on molecular structure.
  • Chelate complexes such as tris(8-quinolinolato)aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxadiazole derivatives, or the like are known. It is reported that electroluminescence from blue to red light in the visible region can be obtained using these materials, and realization of color display devices is being expected.
  • Idemitsu Kosan s DPVBi For blue electroluminescent materials, a lot of materials have been commercialized following Idemitsu Kosan s DPVBi (Compound a). In addition to the Idemitsu Kosan’s blue material system, Kodak’s dinaphthylanthracene (Compound b) and tetra(t-butyl)perylene (Compound c) are known, but more researches and developments are necessary. Until now, Idemitsu Kosan’s distyryl compound system is known to have the best efficiency. It exhibits a power efficiency of 6 lm/W and an operation life of 30,000 hours or longer. However, because of degraded color purity with operation time, its operation life in a full-color display is only thousands of hours.
  • blue electroluminescence becomes advantageous in terms of luminescence efficiency if the electroluminescence wavelength is shifted a little toward a longer wavelength. But, then, it is not applicable to high-quality displays because pure blue color is not attained. Therefore, researches and developments to improve color purity, efficiency and thermal stability are highly required.
  • the inventors of the present invention have made efforts to solve the aforesaid problem. As a result, they have invented a new electroluminescent compound having excellent luminescence efficiency and capable of embodying an organic electroluminescent device with remarkably improved operation life.
  • an object of the present invention is to provide an organic electroluminescent compound having luminescence efficiency and device operation life improved over existing dopant materials and having superior backbone with appropriate color coordinates in order to solve the aforesaid problems.
  • Another object of the present invention is to provide an organic electroluminescent device employing the organic electroluminescent compound as an electroluminescent material.
  • the present invention provides an organic electroluminescent compound represented by Chemical Formula 1 and an organic electroluminescent device including the same.
  • the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life.
  • R 1 through R 3 independently represent (C1-C60)alkyl, (C1-C60)alkoxy, (C6-C60)aryl, (C2-C60)heteroaryl or (C3-C60)cycloalkyl, or R 1 , R 2 or R 3 is linked with Ar 1 via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form a fused ring, and the alkyl, alkoxy, aryl, heteroaryl or cycloalkyl of R 1 through R 3 may be further substituted with one or more substituent(s) selected from a group consisting of (C1-C60)alkyl, (C6-C60)aryl and (C2-C60)heteroaryl;
  • Ar 1 and Ar 2 independently represent a chemical bond, (C6-C60)arylene or (C2-C60)heteroarylene containing one or more heteroatom(s) selected from N, O, S and Se;
  • Ar 3 and Ar 4 independently represent (C1-C60)alkyl, (C6-C60)aryl, (C2-C60)heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, mono-, di- or tri-(C15-C60)spirocyclic, (C10-C60)heterospirocyclic containing one or more heteroatom(s) selected from N, O and S, adamantyl or , or Ar 3 and Ar 4 are linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ringt of or mafusedring, and the carbon atom of the alkylene may be substituted with O, S, NR 24 or SiR 25 R 26 ;
  • R 4 through R 11 independently represent hydrogen, (C1-C60)alkyl, halo(C1-C60)alkyl, (C1-C60)alkoxy, morpholino, thiomorpholino, piperidino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, (C7-C60)bicycloalkyl, adamantyl, halogen, cyano, (C6-C60)aryl, (C2-C60)heteroaryl, tri(C1-C60)alkylsilyl, di(C1-C60)alkyl(C6-C60)arylsilyl or tri(C6-C60)arylsilyl, or R 4 and R 5 , R 7 and R 8 , or R 10 and R 11 are independently linked via (C3-C12)alkylene or (C3-C12)alken
  • R 21 through R 26 independently represent hydrogen, (C1-C60)alkyl, halo(C1-C60)alkyl, (C1-C60)alkoxy, morpholino, thiomorpholino, piperidino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, adamantyl, halogen, cyano, (C6-C60)aryl, (C2-C60)heteroaryl, tri(C1-C60)alkylsilyl, di(C1-C60)alkyl(C6-C60)arylsilyl or tri(C6-C60)arylsilyl, or R 25 and R 26 are linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form a spiro ring or a fused ring;
  • a represents an integer from 1 to 4.
  • the substituents including ‘(C1-C60)alkyl’ may have 1 to 60 carbon atoms, specifically 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms.
  • the substituents including ‘(C6-C60)aryl’ may have 6 to 60 carbon atoms, specifically 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms.
  • the substituents including ‘(C3-C60)heteroaryl’ may have 3 to 60 carbon atoms, specifically 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms.
  • the substituents including ‘(C3-C60)cycloalkyl’ may have 3 to 60 carbon atoms, specifically 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms.
  • the substituents including ‘(C2-C60)alkenyl or alkynyl’ may have 2 to 60 carbon atoms, specifically 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
  • alkyl includes a linear or branched saturated primary hydrocarbon radical consisting only of carbon and hydrogen atoms, or a combination thereof
  • alkyloxy means -O-alkyl, where the alkyl is the same as defined above.
  • aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
  • heteroaryl means an aryl group containing 1 to 4 heteroatom(s) selected from nitrogen (N), oxygen (O) and sulfur (S) as aromatic ring backbone atom(s), other remaining aromatic ring backbone atoms being carbon. It may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with a benzene ring, and may be partially saturated. Further, the heteroaryl includes more than one heteroaryls linked by chemical bond(s). The heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, N-oxide or quaternary salt.
  • monocyclic heteroaryl such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuryl, benzothienyl, isobenzofuryl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, c
  • spirocyclic means a hydrocarbon group in which two rings share only one atom (sp 3 carbon).
  • the atom shared by the two rings is called the spiroatom (‘spiro’ is a Greek word meaning spiral) and may be carbon or silicon.
  • heterospirocyclic means spirocyclic consisting of carbon atoms and one or more heteroatom(s) selected from N, S and O, with the proviso that the heteroatoms are not adjacent to each other.
  • the organic electroluminescent compound of the present invention includes a compound represented by Chemical Formula 2:
  • R 1 through R 3 , X 1 , X 2 , Y 1 , Y 2 and Ar 1 through Ar 4 are the same as defined in Chemical Formula 1.
  • R 1 through R 3 may independently represent methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, benzyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, n-pentoxy, i-pentoxy, n-hexyloxy, n-heptoxy, phenyl, tolyl, butylphenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl
  • R 1 , R 2 or R 3 may be linked with Ar 1 via , , , , , , or to form a fused ring.
  • R 4 through R 10 independently represent hydrogen, (C1-C60)alkyl, halo(C1-C60)alkyl, (C1-C60)alkoxy, morpholino, thiomorpholino, piperidino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, (C7-C60)bicycloalkyl, adamantyl, halogen, cyano, (C6-C60)aryl, (C2-C60)heteroaryl, tri(C1-C60)alkylsilyl, di(C1-C60)alkyl(C6-C60)arylsilyl or tri(C6-C60)arylsilyl, or R 4 and R 5 , R 7 and R 8 or R 10 and R 11 are linked via (C3-C12)alkylene or (C3-C12)alkenylene with
  • the alkyl, alkoxy, heterocycloalkyl, cycloalkyl, bicycloalkyl, adamantyl, aryl, heteroaryl, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R 4 through R 11 may be further substituted with one or more substituent(s) selected from (C1-C60)alkyl, halo(C1-C60)alkyl, (C1-C60)alkoxy, piperidino, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, halogen, cyano, (C6-C60)aryl, (C2-C60)heteroaryl, (C6-C60)ar(C1-C60)alkyl, (C1-C60)alkyl(C6-C60)aryl, tri
  • Ar 1 and Ar 2 may independently represent a chemical bond, or arylene or heteroarylene selected from the following structures, but are not limited thereto:
  • R 31 through R 36 independently represent hydrogen, (C1-C60)alkyl, halo(C1-C60)alkyl, (C1-C60)alkoxy, piperidino, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, halogen, cyano, (C6-C60)aryl, (C2-C60)heteroaryl, (C6-C60)ar(C1-C60)alkyl, tri(C1-C60)alkylsilyl, di(C1-C60)alkyl(C6-C60)arylsilyl or tri(C6-C60)arylsilyl.
  • Ar 1 and Ar 2 may independently represent a chemical bond, or arylene or heteroarylene selected from the following structures, but are not limited thereto:
  • Ar 3 and Ar 4 may independently represent (C1-C60)alkyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, adamantyl, or aryl or heteroaryl selected from the following structures.
  • Ar 3 and Ar 4 may be linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form a fused ring, and the carbon atom of the alkylene may be substituted with O, S, NR 24 or SiR 25 R 26 .
  • the alkyl, aryl, heteroaryl, heterocycloalkyl, cycloalkyl, spirocyclic, heterospirocyclic or adamantyl of Ar 3 and Ar 4 , the fused ring formed as Ar 3 and Ar 4 are linked via alkylene or alkenylene with or without a fused ring may be further substituted with one or more substituent(s) selected from (C1-C60)alkyl, halo(C1-C60)alkyl, (C1-C60)alkoxy, piperidino, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, halogen, cyano, (C6-C60)aryl, (C2-C60)heteroaryl, (C6-C60)ar(C1-C60)alkyl, (C1-C60
  • R 42 through R 52 independently represent hydrogen, (C1-C60)alkyl, halo(C1-C60)alkyl, (C1-C60)alkoxy, piperidino, morpholino, thiomorpholino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C60)cycloalkyl, halogen, cyano, (C6-C60)aryl, (C2-C60)heteroaryl, (C6-C60)ar(C1-C60)alkyl, (C1-C60)alkyl(C6-C60)aryl, tri(C1-C60)alkylsilyl, di(C1-C60)alkyl(C6-C60)arylsilyl or tri(C6-C60)arylsilyl, R 44 and R 45 may be linked via (C3-C60)alkylene or (C3-C60)
  • b represents an integer from 1 to 5.
  • Ar 3 and Ar 4 may be independently represent methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, benzyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, morpholinyl, thiomorpholinyl or
  • Ar 3 and Ar 4 are linked via alkylene or alkenylene may be selected from the following structures, but are not limited thereto:
  • R 61 through R 63 independently represent hydrogen, (C1-C60)alkyl or (C6-C60)aryl, or R 61 and R 62 are linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form a fused ring.
  • organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but are not limited thereto:
  • organic electroluminescent compound according to the present invention may be prepared by Scheme 1, without being limited thereto:
  • the present invention provides an organic electroluminescent device including: 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 compound(s) represented by Chemical Formula 1.
  • the organic layer may include one or more of the organic electroluminescent compound Chemical Formula 1 as an electroluminescent dopant and may include one or more host(s).
  • the host used in the organic electroluminescent device of the present invention is not particularly limited, but may be selected from the compounds represented by Chemical Formula 3 or Chemical Formula 4. Specific structures of the host compounds represented by Chemical Formula 3 or Chemical Formula 4 are exemplified in ⁇ 162> through ⁇ 210> in Korean Patent Application No. 10-2008-0060393, but are not limited thereto.
  • L 1 represents (C6-C60)arylene or (C4-C60)heteroarylene
  • L 2 represents anthracenylene
  • Ar 11 through Ar 14 are independently selected from hydrogen, (C1-C60)alkyl, (C1-C60)alkoxy, halogen, (C4-C60)heteroaryl, (C5-C60)cycloalkyl and (C6-C60)aryl, and the cycloalkyl, aryl or heteroaryl of Ar 11 through Ar 14 may be further substituted with one or more substituent(s) selected from a group consisting of (C6-C60)aryl or (C4-C60)heteroaryl with or without a substituent selected from a group consisting of (C1-C60)alkyl, halo(C1-C60)alkyl, (C1-C60)alkoxy, (C3-C60)cycloalkyl, halogen, cyano, tri(C1-C60)alkylsilyl, di(C1-C60)alkyl(C6-C60)arylsilyl and tri(C6
  • c, d, e and f independently represent an integer from 0 to 4.
  • the electroluminescent layer is a layer where electroluminescence occurs and may be formed of a single layer or two or more layers.
  • the electroluminescent host according to the present invention provides remarkable improvement in luminescence efficiency.
  • the doping concentration may be 0.5 to 10 wt%.
  • the electroluminescent host according to the present invention provides excellent conductivity for holes and electrons, as well as very superior stability and remarkably improved luminescence efficiency and operation life.
  • the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
  • the arylamine compounds or styrylarylamine compounds are exemplified in ⁇ 212> through ⁇ 224> in Korean Patent Application No. 10-2008-0060393, but are not limited thereto.
  • the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, 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.
  • the organic layer may include an electroluminescent layer and a charge generating layer.
  • An organic electroluminescent device having a pixel structure of independent light-emitting mode may be embodied, wherein the organic electroluminescent device including the organic electroluminescent compound represented by Chemical Formula 1 of the present invention as a subpixel and or more subpixel(s) including one or more metal compound(s) selected from a group consisting of Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag are patterned in parallel at the same time.
  • the organic layer may include, in addition to the organic electroluminescent compound, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device.
  • an organic electroluminescent device it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant.
  • a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant.
  • the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated.
  • the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated.
  • Preferable oxidative dopants include various Lewis acids and acceptor compounds.
  • Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • the organic electroluminescent compound according to the present invention has good blue luminescence efficiency and excellent life property, it may be used to manufacture an OLED device having very superior operation life.
  • An OLED device was manufactured using the electroluminescent material according to the present invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) 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 deposition apparatus, which was then ventilated up to 10 -6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • 2-TNATA 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
  • NPB N,N '-bis(-naphthyl)- N , N '-diphenyl-4,4'-diamine
  • an electroluminescent layer was formed thereon as follows.
  • DNA (Examples 1 to 4), Compound H-78 (Examples 5 to 8) or Compound H-89 (Examples 9 to 11) was placed in a cell of the vacuum vapor deposition apparatus as host, and the organic electroluminescent compound according to the present invention was placed in another cell as a dopant.
  • the two materials were vapor-deposited at a rate of 100:1 to form an electroluminescent layer having a thickness of 30 nm on the hole transport layer.
  • Alq tris(8-hydroxyquinoline)-aluminum(III)
  • Liq lithium quinolate
  • an Al cathode was vapor-deposited with a thickness of 150 nm using another vacuum vapor deposition apparatus to manufacture an OLED.
  • Each compound used in the OLED had been purified by vacuum sublimation at 10 -6 torr.
  • blue-emitting DNA was placed in another cell of the vacuum vapor deposition apparatus as host, and Compound A was placed in still another cell.
  • the two materials were vapor-deposited at a rate of 100:1 to form an electroluminescent layer having a thickness of 30 nm on the hole transport layer.
  • an Al cathode was vapor-deposited with a thickness of 150 nm using another vacuum vapor deposition apparatus to manufacture an OLED.
  • Luminescence efficiency of the OLED devices manufactured in Example 1 and Comparative Example 1 was measured at 1,000 cd/m 2 . The result is given in Table 2.
  • the organic electroluminescent compounds of the present invention provide pure blue color as compared to the existing electroluminescent compound. Especially, Compound 47 provides pure blue color while exhibiting an efficiency comparable to that of the existing electroluminescent material. As described, the organic electroluminescent compound of the present invention can be used as a blue-emitting material to provide a color close to the NTSC standard in an organic electroluminescent display.

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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne de nouveaux composés électroluminescents organiques, et un dispositif électroluminescent organique comprenant ces composés. Les composés électroluminescents organiques de l'invention font preuve d'un rendement lumineux élevé dans le bleu et d'une excellente durée de vie. Il en résulte que ces composés conviennent à la fabrication de diodes électroluminescentes organiques se distinguant par une très bonne durée de vie utile.
PCT/KR2010/003456 2009-06-02 2010-05-31 Nouveaux composés électroluminescents organiques, et dispositif électroluminescent organique utilisant ces composés WO2010140801A1 (fr)

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JP2012513864A JP5651689B2 (ja) 2009-06-02 2010-05-31 新規有機電界発光化合物およびこれを使用する有機電界発光素子

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WO2015114102A1 (fr) * 2014-02-03 2015-08-06 Basf Se Azadibenzofuranes substitués par silyle et azadibenzothiophènes
US9401481B2 (en) 2012-01-03 2016-07-26 Samsung Display Co., Ltd. Compound and organic light-emitting device including the same

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