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WO2010140802A1 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDF

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Publication number
WO2010140802A1
WO2010140802A1 PCT/KR2010/003457 KR2010003457W WO2010140802A1 WO 2010140802 A1 WO2010140802 A1 WO 2010140802A1 KR 2010003457 W KR2010003457 W KR 2010003457W WO 2010140802 A1 WO2010140802 A1 WO 2010140802A1
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Prior art keywords
alkyl
tri
arylsilyl
organic electroluminescent
aryl
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PCT/KR2010/003457
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French (fr)
Inventor
Seung Soo Yoon
Sung Min Kim
Bong Ok Kim
Hyuck Joo Kwon
Sung Jin Eum
Young Jun Cho
Young Gil Kim
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Dow Advanced Display Materials Ltd
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Dow Advanced Display Materials Ltd
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Priority to JP2012513865A priority Critical patent/JP2012528853A/en
Priority to CN2010800349455A priority patent/CN102575155A/en
Publication of WO2010140802A1 publication Critical patent/WO2010140802A1/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—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
    • C07F7/0816—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 comprising Si as a ring atom
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Definitions

  • the present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device 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 employing 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.
  • A represents hydrogen or ;
  • 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 and S, wherein the carbon atom of the heteroarylene may be further substituted with Se;
  • At least one of Z 1 through Z 5 and at least one of Z 11 through Z 15 is are nitrogen atoms and the remainder are carbon atoms, wherein the nitrogen atom has no substituent;
  • R 1 through R 5 and R 11 through R 15 independently represent hydrogen, deuterium, (C1-C60)alkyl, (C3-C60)cycloalkyl, (C6-C60)aryl, (C2-C60)heteroaryl, (C1-C60)alkoxy, (C6-C60)aryloxy, mono- or di(C1-C60)alkylamino, mono- or di(C6-C60)arylamino, (C6-C60)ar(C1-C60)alkylamino, tri(C1-C60)alkylsilyl, di(C1-C60)alkyl(C6-C60)arylsilyl or tri(C6-C60)arylsilyl, wherein each of R 1 through R 5 or R 11 through R 15 may be linked with a neighboring substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form
  • R 21 represents hydrogen, deuterium, (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;
  • R 31 through R 38 independently represent hydrogen, deuterium, (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 31 and R 32 , R 34 and R 35 or R 37 and R 38 may be independently linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring
  • R 1 through R 5 , R 11 through R 15 , R 21 and R 31 through R 38 may be further substituted with one or more substituent(s) selected from deuterium, (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
  • 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. Further, the aryl includes two ore more aryls linked by chemical bond(s). 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 two ore more 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
  • a spiro ring 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.
  • the organic electroluminescent compound of the present invention includes a compound represented by Chemical Formula 2 or 3:
  • R 1 through R 5 and R 11 through R 15 may independently represent hydrogen, deuterium, CD 3 , 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, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, n-pentoxy, i-pentoxy, n-hexyloxy,
  • R 31 through R 38 independently represent hydrogen, deuterium, (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; and
  • the alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R 21 through R 28 may be further substituted with one or more substituent(s) selected from deuterium, (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(C
  • 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 41 represents deuterium, (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; and
  • n an integer from 0 to 4.
  • 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:
  • 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 4 or Chemical Formula 5. Specific structures of the host compounds represented by Chemical Formula 4 or Chemical Formula 5 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 independently represent hydrogen, deuterium, (C1-C60)alkyl, (C1-C60)alkoxy, halogen, (C4-C60)heteroaryl, (C5-C60)cycloalkyl or (C6-C60)aryl, wherein the cycloalkyl, aryl or heteroaryl of Ar 11 through Ar 14 may be further substituted with one or more substituent(s) selected from (C6-C60)aryl or (C4-C60)heteroaryl substituted or unsubstituted with one or more substituent(s) selected from deuterium, (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)arylsily
  • 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. Accordingly, when the compound represented by Chemical Formula 4 or Chemical Formula 5 is selected as an electroluminescent host, it can considerably compensate for the electrical disadvantage of the organic electroluminescent compound represented by Chemical Formula 1 according to the present invention.
  • 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.
  • the compound emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • a layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. An operation stability may be attained therefrom.
  • the chalcogenide may be, for example, SiO x (1 ⁇ x ⁇ 2), AlO x (1 ⁇ x ⁇ 1.5), SiON, SiAlON, etc.
  • the metal halide may be, for example, LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.
  • the metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • 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.
  • Butylmagnesium chloride (730 mg, 6.3 mmol) was added to a 250 mL flask and dissolved with THF (40 mL). After cooling to -10 °C and adding n-butyllithium (5.1 mL), the mixture was stirred for 1 hour while maintaining the temperature at -10 °C.
  • 3-Bromoquinoline (3.5 g, 17 mmol) dissolved in THF (20 mL) was added to the flask at -30 °C. After raising the temperature to -10 °C, the mixture was stirred for 2 hours.
  • 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
  • N , N '-bis(-naphthyl)- N , N '-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • an electroluminescent layer was formed thereon as follows.
  • DNA (Examples 1 to 4) or Compound H-33 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.
  • blue-emitting DNA was placed in another cell of the vacuum vapor deposition apparatus as host, and Compound B 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 Examples 1-7 and Comparative Examples 1 and 2 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 2 provides an efficiency improved by 38% as compared to the existing electroluminescent material (Compound B). As described, the organic electroluminescent compound of the present invention can be used as a blue-emitting material to provide advantages in brightness and power consumption of existing full-color OLEDs.

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Abstract

Provided are novel organic electroluminescent compounds and an organic electroluminescent device including the same. The disclosed organic electroluminescent compounds exhibit high luminescence efficiency in blue color and excellent life property. Thus, they may be used to manufacture OLEDs having very good operation life.

Description

NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
The present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device 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 employing the same as a dopant.
Among display devices, electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices. In 1987, 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].
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.
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. In general, 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.
Figure PCTKR2010003457-appb-I000001
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.
Accordingly, 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.
In one general aspect, the present invention provides an organic electroluminescent compound represented by Chemical Formula 1 and an organic electroluminescent device including the same. With superior luminescence efficiency and excellent life property, the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life.
Figure PCTKR2010003457-appb-I000002
(1)
wherein
A represents hydrogen or
Figure PCTKR2010003457-appb-I000003
;
Ar1 and Ar2 independently represent a chemical bond, (C6-C60)arylene or (C2-C60)heteroarylene containing one or more heteroatom(s) selected from N, O and S, wherein the carbon atom of the heteroarylene may be further substituted with Se;
at least one of Z1 through Z5 and at least one of Z11 through Z15 is are nitrogen atoms and the remainder are carbon atoms, wherein the nitrogen atom has no substituent;
R1 through R5 and R11 through R15 independently represent hydrogen, deuterium, (C1-C60)alkyl, (C3-C60)cycloalkyl, (C6-C60)aryl, (C2-C60)heteroaryl, (C1-C60)alkoxy, (C6-C60)aryloxy, mono- or di(C1-C60)alkylamino, mono- or di(C6-C60)arylamino, (C6-C60)ar(C1-C60)alkylamino, tri(C1-C60)alkylsilyl, di(C1-C60)alkyl(C6-C60)arylsilyl or tri(C6-C60)arylsilyl, wherein each of R1 through R5 or R11 through R15 may be linked with a neighboring substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form a fused ring, the carbon atom of the alkylene may be further substituted with O, S or NR21, and the CH of the alkenylene may be further substituted with N;
R21 represents hydrogen, deuterium, (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;
X and Y independently represent a chemical bond, -(CR31R32)n-, -N(R33)-, -Si(R34)(R35)-, -O-, -S-, -Se-, -P(R36)- or -(R37)C=C(R38)-, wherein n is an integer from 1 to 4;
R31 through R38 independently represent hydrogen, deuterium, (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 R31 and R32, R34 and R35 or R37 and R38 may be independently linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form a spiro ring or a fused ring; and
the arylene or heteroarylene of Ar1 and Ar2, and the alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylamino, arylamino, aralkylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R1 through R5, R11 through R15, R21 and R31 through R38 may be further substituted with one or more substituent(s) selected from deuterium, (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 and tri(C6-C60)arylsilyl.
In the present invention, 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.
In the present invention, ‘alkyl’ includes a linear or branched saturated primary hydrocarbon radical consisting only of carbon and hydrogen atoms, or a combination thereof, and ‘alkyloxy’ means -O-alkyl, where the alkyl is the same as defined above.
In the present invention, ‘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. Further, the aryl includes two ore more aryls linked by chemical bond(s). Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
In the present invention, ‘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 two ore more 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. Specific examples include 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, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, benzodioxolyl, etc., N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide, etc.), quaternary salt thereof, etc., but are not limited thereto.
In the present invention, ‘a spiro ring’ means a hydrocarbon group in which two rings share only one atom (sp3 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.
The organic electroluminescent compound of the present invention includes a compound represented by Chemical Formula 2 or 3:
Figure PCTKR2010003457-appb-I000004
(2)
Figure PCTKR2010003457-appb-I000005
(3)
wherein X, Y, Ar1, Ar2, Z1 through Z5, Z11 through Z15, R1 through R15 and R11 through R15 are the same as defined in Chemical Formula 1.
R1 through R5 and R11 through R15 may independently represent hydrogen, deuterium, CD3, 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, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, n-pentoxy, i-pentoxy, n-hexyloxy, n-heptoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, C6D5, phenyl, tolyl, butylphenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, benzofuranyl, benzothiophenyl, pyrazolyl, indolyl, carbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, phenoxy, dimethylamino, monomethylamino, benzylamino, trimethylsilyl, triethylsilyl, tripropylsilyl, tri(t-butyl)silyl, t-butyldimethylsilyl, dimethylphenylsilyl or triphenylsilyl, or each of R1 through R5 or R11 through R15 may be linked to an adjacent substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form a fused ring, and the CH of the alkenylene may be further substituted with N.
Figure PCTKR2010003457-appb-I000006
and
Figure PCTKR2010003457-appb-I000007
may be independently selected from the following structures, but are not limited thereto:
Figure PCTKR2010003457-appb-I000008
Figure PCTKR2010003457-appb-I000009
may be selected from the following structures, but is not limited thereto:
Figure PCTKR2010003457-appb-I000010
Figure PCTKR2010003457-appb-I000011
Figure PCTKR2010003457-appb-I000012
Figure PCTKR2010003457-appb-I000013
wherein
R31 through R38 independently represent hydrogen, deuterium, (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; and
the alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R21 through R28 may be further substituted with one or more substituent(s) selected from deuterium, (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 and tri(C6-C60)arylsilyl.
Ar1 and Ar2 may independently represent a chemical bond, or arylene or heteroarylene selected from the following structures, but are not limited thereto:
Figure PCTKR2010003457-appb-I000014
wherein
R41 represents deuterium, (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; and
m represents an integer from 0 to 4.
More specifically, Ar1 and Ar2 may independently represent a chemical bond, or arylene or heteroarylene selected from the following structures, but are not limited thereto:
Figure PCTKR2010003457-appb-I000015
The organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but are not limited thereto:
Figure PCTKR2010003457-appb-I000016
Figure PCTKR2010003457-appb-I000017
Figure PCTKR2010003457-appb-I000018
The organic electroluminescent compound according to the present invention may be prepared by Scheme 1, without being limited thereto:
[Scheme 1]
Figure PCTKR2010003457-appb-I000019
wherein X, Y, Ar1, Ar2, Z1 through Z5, Z11 through Z15, R1 through R15 and R11 through R15 are the same as defined in Chemical Formula 1.
In another general aspect, 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 4 or Chemical Formula 5. Specific structures of the host compounds represented by Chemical Formula 4 or Chemical Formula 5 are exemplified in <162> through <210> in Korean Patent Application No. 10-2008-0060393, but are not limited thereto.
(Ar11)c-L1-(Ar12)d (4)
(Ar13)e-L2-(Ar14)f (5)
wherein
L1 represents (C6-C60)arylene or (C4-C60)heteroarylene;
L2 represents anthracenylene;
Ar11 through Ar14 independently represent hydrogen, deuterium, (C1-C60)alkyl, (C1-C60)alkoxy, halogen, (C4-C60)heteroaryl, (C5-C60)cycloalkyl or (C6-C60)aryl, wherein the cycloalkyl, aryl or heteroaryl of Ar11 through Ar14 may be further substituted with one or more substituent(s) selected from (C6-C60)aryl or (C4-C60)heteroaryl substituted or unsubstituted with one or more substituent(s) selected from deuterium, (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-C60)arylsilyl, deuterium, (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-C60)arylsilyl; and
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. When a host-dopant system according to the present invention is used, the electroluminescent host according to the present invention provides remarkable improvement in luminescence efficiency. The doping concentration may be 0.5 to 10 wt%. When compared with existing other host materials, 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. Accordingly, when the compound represented by Chemical Formula 4 or Chemical Formula 5 is selected as an electroluminescent host, it can considerably compensate for the electrical disadvantage of the organic electroluminescent compound represented by Chemical Formula 1 according to the present invention.
In the organic electronic device of the present invention, 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. Specifically, 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.
Further, in the organic electroluminescent device of the present invention, 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.
Further, 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. The compound emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
In the organic electroluminescent device of the present invention, a layer (hereinafter referred to as ‘surface layer’) selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. An operation stability may be attained therefrom. The chalcogenide may be, for example, SiOx (1 ≤ x ≤ 2), AlOx (1 ≤ x ≤ 1.5), SiON, SiAlON, etc. The metal halide may be, for example, LiF, MgF2, CaF2, a rare earth metal fluoride, etc. The metal oxide may be, for example, Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
In an organic electroluminescent device according to the present invention, 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. In that case, since the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated. In addition, since 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.
Since 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.
The present invention is further described with respect to organic electroluminescent compounds according to the present invention, processes for preparing the same, and luminescence properties of devices employing the same. However, the following examples are provided for illustrative purposes only and they are not intended to limit the scope of the present invention.
[Preparation Example 1] Preparation of Compound 2
Figure PCTKR2010003457-appb-I000020
Preparation of Compound A
9,9-Diethyl-9H-fluorene (7 g, 32.11 mmol) and paraformaldehyde (9.4 g, 32.11 mmol) were added to a 100 mL round-bottom flask. After drying in vacuum, nitrogen gas was injected. After adding 30% HBr (50 mL) to the flask, the mixture was heated to 60 ℃ and stirred for 24 hours. After the reaction was completed, extraction was performed using CHCl3. After washing 3 times with NaHCO3, the product was washed 3 times with brine. Compound A (13 g, 31.8 mmol, 99%) was obtained.
Preparation of Compound B
Compound A (5.00g, 12.24 mmol) was added to a 50 mL round-bottom flask. After drying in vacuum, nitrogen gas was injected. After adding triethyl phosphite (8.1 mL, 48.96 mmol), the mixture was stirred at 185 ℃ for 6 hours under reflux. After the reaction was completed, remaining triethyl phosphite was removed using a vacuum distiller. After washing with distilled water, extraction was performed with ethyl acetate. The organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. Purification by column chromatography using ethyl acetate as an eluent yielded Compound B (4.9 g, 9,37 mmol, 76%).
Preparation of Compound C
2-Bromoquinoline (5 g, 24 mmol), 4-formylphenylboronic acid (3.59 g, 24 mmol) and tetrakis(triphenylphosphine)palladium (1.11 g, 0.96 mmol) were added to a 1000 mL round-bottom flask and dissolved with toluene (168 mL). After adding 2.0 M sodium carbonate aqueous solution (84 mL, 168.2 mmol) and ethanol (84 mL) to the flask, the mixture was stirred at 120 ℃ for 2 hours under reflux. After the reaction was completed, extraction was performed with ethyl acetate. Purification by column chromatography yielded Compound C (5 g, 21.4 mmol, 89%).
Preparation of Compound 2
Compound B (5 g, 9.56 mmol) and Compound C (4.46 g, 19.13 mmol) were added to a 250 mL round-bottom flask. After drying in vacuum, nitrogen gas was injected. After adding THF (50 mL), potassium tert-butoxide (1.0 M in THF, 19 mL, 19.13 mmol) was slowly added at 0 ℃ and the mixture was stirred for 10 minutes. After heating to room temperature, the mixture was further stirred for 1 hour. After the reaction was completed, excess distilled water was added and thus formed precipitate was filtered. The filtered solid was washed with ethanol and purified to obtain Compound 2 (3.25 g, 4.78 mmol, 50%).
1H NMR (CDCl3, 200 MHz) = 0.9 (6H, m), 1.91 (4H, m), 6.95 (4H, m), 7.35 (2H, m), 7.54-7.6 (8H, m), 7.71 (2H, m), 7.78 (2H, m), 7.87 (2H, m), 7.98 (2H, m), 8.06-8.1 (4H, m), 8.3 (4H, m).
[Preparation Example 2] Preparation of Compound 63
Figure PCTKR2010003457-appb-I000021
Preparation of Compound 63
Compound B (5 g, 9.56 mmol) and quinoline-2-carbaldehyde (3 g, 19.13 mmol) were added to a 250 mL round-bottom flask. After drying in vacuum, nitrogen gas was injected. After adding THF (50 mL), potassium tert-butoxide (1.0 M in THF, 19 mL, 19.13 mmol) was slowly added at 0 ℃ and the mixture was stirred for 10 minutes. After heating to room temperature, the mixture was further stirred for 1 hour. After the reaction was completed, excess distilled water was added and thus formed precipitate was filtered. The filtered solid was washed with ethanol and purified to obtain Compound 63 (4.5 g, 8.51 mmol, 90%).
1H NMR (CDCl3, 200 MHz) = 0.9 (6H, m), 1.91 (4H, m), 7.2 (2H, m), 7.37-7.42 (4H, m), 7.56-7.6 (6H, m), 7.78-7.82 (4H, m), 7.98 (2H, m), 8.06 (2H, m), 8.24 (2H, m).
[Preparation Example 3] Preparation of Compound 64
Figure PCTKR2010003457-appb-I000022
Preparation of Compound F
Butylmagnesium chloride (730 mg, 6.3 mmol) was added to a 250 mL flask and dissolved with THF (40 mL). After cooling to -10 ℃ and adding n-butyllithium (5.1 mL), the mixture was stirred for 1 hour while maintaining the temperature at -10 ℃. 3-Bromoquinoline (3.5 g, 17 mmol) dissolved in THF (20 mL) was added to the flask at -30 ℃. After raising the temperature to -10 ℃, the mixture was stirred for 2 hours. 2,5-Dibromopyridine (4 g, 17 mmol) dissolved in THF (30 mL) was added along with Pd(dba)2 (480 mg, 830 mol) and dppf (470 mg, 830 mol). After stirring for 1 hour at -10 C and heating to room temperature, the mixture was stirred for 18 hours. Then, saturated NH4Cl aqueous solution was added to terminate the reaction. After extracting with ethyl acetate, the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. Purification by column chromatography yielded Compound F (2.5 g, 8.76 mmol, 53%).
Preparation of Compound G
Compound F (2.5 g, 10.7 mmol) was added to a 100 mL round-bottom flask. After drying in vacuum, argon gas was injected. After adding THF (25 mL) and cooling to -78 ℃, n-butyllithium (5 mL, 12.84 mmol) was slowly added and the mixture was stirred for 1 hour while maintaining the low temperature. After adding DMF (1 mL, 12.84 mmol) at -78 ℃, the mixture was stirred for 1 hour. After the reaction was completed, 1 M HCl was added at 0 ℃. After washing with distilled water and extracting with ethyl acetate, the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. Purification by column chromatography yielded Compound G (1.68 g, 7.17 mmol, 82%).
Preparation of Compound 64
Compound G (1.68 g, 7.17 mmol) and Compound B (1.7 g, 3.25 mmol) were added to a 250 mL round-bottom flask. After drying in vacuum, nitrogen gas was injected. After adding THF (20 mL) and slowly adding potassium tert-butoxide (1.0 M in THF, 3.25 mL, 3.25 mmol) at 0 ℃, the mixture was stirred for 10 minutes. After heating to room temperature, the mixture was stirred for 1 hour. After the reaction was completed, extraction was performed with ethyl acetate. The organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. Purification by column chromatography yielded Compound 64 (1.55 g, 2.26 mmol, 70%).
1H NMR (CDCl3, 200 MHz) = 0.9 (6H, m), 1.91 (4H, m), 6.95 (4H, m), 7.42 (2H, m), 7.59-7.6 (4H, m), 7.68 (2H, m), 7.78-7.82 (4H, m), 7.98 (2H, m), 8.06 (2H, m), 8.29-8.36 (6H, m), 8.93 (2H, m).
[Preparation Example 4] Preparation of Compound 65
Figure PCTKR2010003457-appb-I000023
Preparation of Compound H
2-Bromo-9,9-diethyl-9H-fluorene (10 g, 33.19 mmol) was added to a 500 mL round-bottom flask. After drying in vacuum, argon gas was injected. After adding THF (250 mL) and cooling to -78 ℃, n-butyllithium (19.9 mL, 49.79 mmol) was slowly added. After stirring for 1 hour while maintaining the low temperature, DMF (3.8 mL, 49.79 mmol) was added at -78 ℃ and the mixture was stirred for 1 hour. After the reaction was completed, 1 M HCl was added at 0 ℃. After washing with distilled water and extracting with EA, the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. Purification by column chromatography yielded Compound H (6 g, 72%).
Preparation of Compound J
Compound I (6.7 g, 28.72 mmol) was added to a 100 mL round-bottom flask. After adding THF (50 mL) and cooling to 0 ℃, NaBH4 (1.4 g, 37.34 mmol) and MeOH (6 mL) were added. Then, the mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, after washing with distilled water and extracting with EA, the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. Purification by column chromatography yielded Compound J (6 g, 89%).
Preparation of Compound K
Compound J (6 g, 25.50 mmol) was added to a 50 mL round-bottom flask. After adding P(OEt)3 (8.5 mL, 51.0 mmol) and cooling to 0 ℃, I2 (6.4 g, 25.50 mmol) was slowly added and the mixture was stirred at 0 ℃ for 10 minutes. Then, reflux was carried out at 120 ℃ overnight. After the reaction was completed, P(OEt)3 was removed by distillation. After washing with distilled water and extracting with EA, the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. Purification by column chromatography yielded Compound K (5.1 g, 59%).
Preparation of Compound 65
Compound H (3 g, 11.98 mmol) and Compound K (4.8 g, 14.38 mmol) were added to a 250 mL round-bottom flask. After drying in vacuum, argon gas was injected. After adding THF (100 mL) and cooling to 0 ℃, 1 M KO(t-Bu) (14.3 mL, 14.38 mmol) was slowly added and the mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, after washing with distilled water and extracting with EA, the organic layer was dried with MgSO4 and the solvent was removed using a rotary evaporator. Purification by column chromatography yielded Compound 65 (3.3 g, 61%).
1H NMR (CDCl3, 200 MHz) = 0.9 (6H, m), 1.91 (4H, m), 6.95 (2H, m), 7.28 (1H, m), 7.35-7.38 (2H, m), 7.54-7.6 (5H, m), 7.71 (1H, m), 7.78 (1H, m), 7.87 (2H, m), 7.98 (1H, m), 8.06-8.1 (2H, m), 8.3 (2H, m).
Compounds 1 to 62 were prepared according to the procedure of Preparation Examples 1 to 4. 1H NMR and MS/FAB data of thus prepared organic electroluminescent compounds are given in Table 1.
[Table 1]
Figure PCTKR2010003457-appb-I000024
Figure PCTKR2010003457-appb-I000025
Figure PCTKR2010003457-appb-I000026
Figure PCTKR2010003457-appb-I000027
Figure PCTKR2010003457-appb-I000028
Figure PCTKR2010003457-appb-I000029
Figure PCTKR2010003457-appb-I000030
Figure PCTKR2010003457-appb-I000031
Figure PCTKR2010003457-appb-I000032
Figure PCTKR2010003457-appb-I000033
[Examples 1-7] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
An OLED device was manufactured using the electroluminescent material according to the present invention. First, a transparent electrode ITO thin film (15 Ω/□) 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. Then, 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.
Then, N,N'-bis(-naphthyl)-N,N'-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
Figure PCTKR2010003457-appb-I000034
After forming the hole injection layer and the hole transport layer, an electroluminescent layer was formed thereon as follows. DNA (Examples 1 to 4) or Compound H-33 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.
Figure PCTKR2010003457-appb-I000035
Then, tris(8-hydroxyquinoline)-aluminum(III) (Alq) was vapor-deposited with a thickness of 20 nm as an electron transport layer, and lithium quinolate (Liq) was vapor-deposited with a thickness of 1 to 2 nm as an electron injection layer. Thereafter, an Al cathode was vapor-deposited with a thickness of 150 nm using another vacuum vapor deposition apparatus to manufacture an OLED.
Figure PCTKR2010003457-appb-I000036
Each compound used in the OLED had been purified by vacuum sublimation at 10-6torr.
[Comparative Example 1] Manufacture of OLED device using existing electroluminescent material
After forming a hole injection layer and a hole transport layer in the same manner as Example 1, 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.
Figure PCTKR2010003457-appb-I000037
Then, after forming an electron transport layer and an electron injection layer in the same manner as Example 1, an Al cathode was vapor-deposited with a thickness of 150 nm using another vacuum vapor deposition apparatus to manufacture an OLED.
[Comparative Example 2] Manufacture of OLED device using existing electroluminescent material
After forming a hole injection layer and a hole transport layer in the same manner as Example 1, blue-emitting DNA was placed in another cell of the vacuum vapor deposition apparatus as host, and Compound B 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.
Figure PCTKR2010003457-appb-I000038
Then, after forming an electron transport layer and an electron injection layer in the same manner as Example 1, 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 Examples 1-7 and Comparative Examples 1 and 2 was measured at 1,000 cd/m2. The result is given in Table 2.
[Table 2]
Figure PCTKR2010003457-appb-I000039
As seen from Table 2, the organic electroluminescent compounds of the present invention provide pure blue color as compared to the existing electroluminescent compound. Especially, Compound 2 provides an efficiency improved by 38% as compared to the existing electroluminescent material (Compound B). As described, the organic electroluminescent compound of the present invention can be used as a blue-emitting material to provide advantages in brightness and power consumption of existing full-color OLEDs.

Claims (10)

  1. An organic electroluminescent compound represented by Chemical Formula 1:
    Figure PCTKR2010003457-appb-I000040
    (1)
    wherein
    A represents hydrogen or
    Figure PCTKR2010003457-appb-I000041
    ;
    Ar1 and Ar2 independently represent a chemical bond, (C6-C60)arylene or (C2-C60)heteroarylene containing one or more heteroatom(s) selected from N, O and S, wherein the carbon atom of the heteroarylene may be further substituted with Se;
    at least one of Z1 through Z5 and at least one of Z11 through Z15 is are nitrogen atoms and the remainder are carbon atoms, wherein the nitrogen atom has no substituent;
    R1 through R5 and R11 through R15 independently represent hydrogen, deuterium, (C1-C60)alkyl, (C3-C60)cycloalkyl, (C6-C60)aryl, (C2-C60)heteroaryl, (C1-C60)alkoxy, (C6-C60)aryloxy, mono- or di(C1-C60)alkylamino, mono- or di(C6-C60)arylamino, (C6-C60)ar(C1-C60)alkylamino, tri(C1-C60)alkylsilyl, di(C1-C60)alkyl(C6-C60)arylsilyl or tri(C6-C60)arylsilyl, wherein each of R1 through R5 or R11 through R15 may be linked with a neighboring substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form a fused ring, the carbon atom of the alkylene may be further substituted with O, S or NR21, and the CH of the alkenylene may be further substituted with N;
    R21 represents hydrogen, deuterium, (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;
    X and Y independently represent a chemical bond, -(CR31R32)n-, -N(R33)-, -Si(R34)(R35)-, -O-, -S-, -Se-, -P(R36)- or -(R37)C=C(R38)-, wherein n is an integer from 1 to 4;
    R31 through R38 independently represent hydrogen, deuterium, (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 R31 and R32, R34 and R35 or R37 and R38 may be independently linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form a spiro ring or a fused ring; and
    the arylene or heteroarylene of Ar1 and Ar2, and the alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylamino, arylamino, aralkylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R1 through R5, R11 through R15, R21 and R31 through R38 may be further substituted with one or more substituent(s) selected from deuterium, (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 and tri(C6-C60)arylsilyl.
  2. The organic electroluminescent compound according to claim 1, which is represented by Chemical Formula 2 or 3:
    Figure PCTKR2010003457-appb-I000042
    (2)
    Figure PCTKR2010003457-appb-I000043
    (3)
    wherein
    X, Y, Ar1, Ar2, Z1 through Z5, Z11 through Z15, R1 through R15 and R11 through R15 are the same as defined in claim 1.
  3. The organic electroluminescent compound according to claim 1, wherein Ar1 and Ar2 independently represent a chemical bond or arylene or heteroarylene selected from the following structures:
    Figure PCTKR2010003457-appb-I000044
    wherein
    R41 represents deuterium, (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; and
    m represents an integer from 0 to 4.
  4. The organic electroluminescent compound according to claim 2, wherein
    Figure PCTKR2010003457-appb-I000045
    is selected from the following structures:
    Figure PCTKR2010003457-appb-I000046
    Figure PCTKR2010003457-appb-I000047
    Figure PCTKR2010003457-appb-I000048
    Figure PCTKR2010003457-appb-I000049
    wherein
    R31 through R38 independently represent hydrogen, deuterium, (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; and
    the alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R21 through R28 may be further substituted with one or more substituent(s) selected from deuterium, (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 and tri(C6-C60)arylsilyl.
  5. The organic electroluminescent compound according to claim 2, wherein
    Figure PCTKR2010003457-appb-I000050
    and
    Figure PCTKR2010003457-appb-I000051
    are independently selected from the following structures:
    Figure PCTKR2010003457-appb-I000052
  6. An organic electroluminescent device comprising the organic electroluminescent compound according to any of claims 1 to 5.
  7. The organic electroluminescent device according to claim 6, which is comprised of 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 comprises one or more of the organic electroluminescent compound according to any of claims 1 to 5, and one or more host(s) selected from the compounds represented by Chemical Formula 4 or Chemical Formula 5:
    (Ar11)c-L1-(Ar12)d (4)
    (Ar13)e-L2-(Ar14)f (5)
    wherein
    L1 represents (C6-C60)arylene or (C4-C60)heteroarylene;
    L2 represents anthracenylene;
    Ar11 through Ar14 independently represent hydrogen, deuterium, (C1-C60)alkyl, (C1-C60)alkoxy, halogen, (C4-C60)heteroaryl, (C5-C60)cycloalkyl or (C6-C60)aryl, wherein the cycloalkyl, aryl or heteroaryl of Ar11 through Ar14 may be further substituted with one or more substituent(s) selected from (C6-C60)aryl or (C4-C60)heteroaryl substituted or unsubstituted with one or more substituent(s) selected from deuterium, (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-C60)arylsilyl, deuterium, (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-C60)arylsilyl; and
    c, d, e and f independently represent an integer from 0 to 4.
  8. The organic electroluminescent device according to claim 7, wherein the organic layer further comprises one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, or 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.
  9. The organic electroluminescent device according to claim 7, which emits white light as the organic layer comprises one or more organic electroluminescent layer(s) emitting blue, red or green light at the same time.
  10. The organic electroluminescent device according to claim 7, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9391282B2 (en) 2013-02-22 2016-07-12 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting diode including the same

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030052311A1 (en) * 2001-07-06 2003-03-20 Yoshio Inagaki Two-photon absorption composition
EP1727396A1 (en) * 2004-03-19 2006-11-29 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2007021117A1 (en) * 2005-08-16 2007-02-22 Gracel Display Inc. Green electroluminescent compounds and organic electroluminescent device using the same
US20070098233A1 (en) * 2003-10-22 2007-05-03 Academia Sinica Cancer cell detecting devices
KR20090018503A (en) * 2007-08-17 2009-02-20 삼성전자주식회사 Oxadiazole derivative compound and organic light emitting device having the same
CN101386602A (en) * 2008-10-29 2009-03-18 华南理工大学 White light-emitting s-triazine derivatives, preparation method and application thereof
CN101486902A (en) * 2009-03-02 2009-07-22 西安近代化学研究所 Organic electroluminescent blue luminescence compound
EP2138551A2 (en) * 2008-06-25 2009-12-30 Gracel Display Inc. Fluorene-derivatives and organic electroluminescent device using the same
WO2010006890A1 (en) * 2008-07-18 2010-01-21 Basf Se Azapyrenes for electronic applications

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3991049A (en) * 1967-07-14 1976-11-09 Ciba-Geigy Ag Aromatic compounds containing ethylene double bonds, processes for their manufacture and use
CH523909A (en) * 1969-01-09 1972-06-15 Ciba Geigy Ag Process for the production of heterocyclic compounds containing ethylene double bonds and their use as optical brighteners outside the textile industry
DE2850585A1 (en) * 1978-11-22 1980-06-04 Hoechst Ag PHOTOPOLYMERIZABLE MIXTURE
JP2767113B2 (en) * 1988-10-17 1998-06-18 株式会社リコー Ink sheet for thermal transfer recording
US5859251A (en) * 1997-09-18 1999-01-12 The United States Of America As Represented By The Secretary Of The Air Force Symmetrical dyes with large two-photon absorption cross-sections
JP4235372B2 (en) * 2000-09-28 2009-03-11 富士フイルム株式会社 2,2'-Bridged Biphenyl Compound, Optical Information Recording Medium, and Recording Method
JP2003020469A (en) * 2001-07-06 2003-01-24 Fuji Photo Film Co Ltd Biphoton absorption composition
US20060194073A1 (en) * 2003-03-07 2006-08-31 Masato Okada Organic compound and organic electrolumiscent device
CN1887883A (en) * 2005-06-27 2007-01-03 中国科学院理化技术研究所 V-type conjugated light-absorbing organic salt compound and use thereof
CN101200477A (en) * 2007-08-03 2008-06-18 上海拓引数码技术有限公司 Compound for preparing organic electromechanical phosphorescent material and preparation method thereof
JP5300454B2 (en) * 2008-12-19 2013-09-25 日本化薬株式会社 Dye-sensitized photoelectric conversion element

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030052311A1 (en) * 2001-07-06 2003-03-20 Yoshio Inagaki Two-photon absorption composition
US20070098233A1 (en) * 2003-10-22 2007-05-03 Academia Sinica Cancer cell detecting devices
EP1727396A1 (en) * 2004-03-19 2006-11-29 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
WO2007021117A1 (en) * 2005-08-16 2007-02-22 Gracel Display Inc. Green electroluminescent compounds and organic electroluminescent device using the same
KR20090018503A (en) * 2007-08-17 2009-02-20 삼성전자주식회사 Oxadiazole derivative compound and organic light emitting device having the same
EP2138551A2 (en) * 2008-06-25 2009-12-30 Gracel Display Inc. Fluorene-derivatives and organic electroluminescent device using the same
WO2010006890A1 (en) * 2008-07-18 2010-01-21 Basf Se Azapyrenes for electronic applications
CN101386602A (en) * 2008-10-29 2009-03-18 华南理工大学 White light-emitting s-triazine derivatives, preparation method and application thereof
CN101486902A (en) * 2009-03-02 2009-07-22 西安近代化学研究所 Organic electroluminescent blue luminescence compound

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 2009:345450 *
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 2009:900991 *
FISCHER, E. ET AL.: "`Conformational equilibria in trans 1,2-diarylethylenes manifested in their emission spectra. Part III. (1a). Pyridyl and quinolyl derivatives.", BULLETIN DES SOCIETES CHIMIQUES BELGES., vol. 88, 1979, pages 889 - 895 *
LEBRET, V. ET AL.: "Synthesis and characterization of fluorescently doped mesoporous nanoparticles for two-photon excitation", CHEMISTRY OF MATERIALS., vol. 20, 2008, pages 2174 - 2183 *
VELLIS, P.D. ET AL.: "New divinylene trimers with triphenylpyridine segments: Synthesis, photophysics, electrochemical and electroluminescent properties", SYNTHETIC METALS., vol. 158, 2008, pages 854 - 860, XP025804221, DOI: doi:10.1016/j.synthmet.2008.06.002 *
VELLIS, P.D. ET AL.: "Synthesis ofterpyridine ligands and their complexation with Zn2+ and Ru2+ for optoelectronic applications", JOURNAL OF POLYMER SCIENCE: PART A: POLYMER CHEMISTRY., vol. 46, 2008, pages 7702 - 7712, XP008119410, DOI: doi:10.1002/pola.23073 *
WILD, A. ET AL.: "pi-conjugated 2,2':6',2''-bis(terpyridines): Systematical tuning of the optical properties by variation of the linkage between the terpyridines and the pi- conjugated system", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY., 2010, pages 1859 - 1868, XP055241118, DOI: doi:10.1002/ejoc.200901112 *
ZHOU, H.-P. ET AL.: "Synthesis, crystal structures and photoluminescence of mercury(II) complexes with two homologous novel functional rigid ligands", EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2005, pages 4976 - 4984 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9391282B2 (en) 2013-02-22 2016-07-12 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting diode including the same

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