WO2011136484A1 - 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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WO2011136484A1
WO2011136484A1 PCT/KR2011/002526 KR2011002526W WO2011136484A1 WO 2011136484 A1 WO2011136484 A1 WO 2011136484A1 KR 2011002526 W KR2011002526 W KR 2011002526W WO 2011136484 A1 WO2011136484 A1 WO 2011136484A1
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alkyl
aryl
organic electroluminescent
heteroaryl
cycloalkyl
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PCT/KR2011/002526
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French (fr)
Inventor
Young Gil Kim
Chi Sik Kim
Young Jun Cho
Hyuck Joo Kwon
Sung Min Kim
Bong Ok Kim
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DuPont Specialty Materials Korea Ltd
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Rohm and Haas Electronic Materials Korea Ltd
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Priority to JP2013507866A priority Critical patent/JP5782503B2/en
Priority to CN201180031554.2A priority patent/CN102958906B/en
Publication of WO2011136484A1 publication Critical patent/WO2011136484A1/en
Anticipated expiration legal-status Critical
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Definitions

  • the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same, more particularly, to novel organic electroluminescent compounds used as a blue electroluminescent 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 are generally classified into high-molecular materials and low-molecular materials.
  • the low-molecular materials include metal complexes and thoroughly organic electroluminescent materials which do not contain metal, from the aspect of molecular structure.
  • Such electroluminescent materials include chelate complexes such as tris(8-quinolinolato)aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bis(styrylarylene) derivatives and oxadiazole derivatives. From those materials, it is reported that light emission of visible region from blue to red can be obtained and it is expected that a color display device will be realized.
  • the distryl compound system of Idemitsu-Kosan which is known to have highest efficiency up to now, has 6 lm/W power efficiency and beneficial device lifetime of more than 30,000 hr.
  • the lifetime is merely several thousand hours, owing to decrease of color purity over operation time.
  • blue electroluminescence it becomes advantageous from the aspect of the luminous efficiency, if the electroluminescent wavelength is shifted a little toward longer wavelength.
  • it is not easy to apply the material to a display of high quality because of unsatisfactory color purity in blue.
  • the research and development of such materials are urgent because of the problems in color purity, efficiency and thermal stability.
  • the object of the present invention is to provide organic electroluminescent compounds having the backbone with appropriate color coordinates to provide better luminous efficiency and device life compared with conventional dopant material, while overcoming the problems described above, and a highly efficient and long life organic electroluminescent device using the organic electroluminescent compounds.
  • novel organic electroluminescent compounds and an organic electroluminescent device using the same.
  • the organic electroluminescent compound is a compound represented by Chemical Formula 1. With superior luminescence efficiency in blue color 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.
  • Ar 1 through Ar 4 independently represent (C6-C30)aryl, (C2-C30)heteroaryl containing one or more heteroatom(s) selected from N, O and S, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, adamantyl, (C7-C30)bicycloalkyl or , or Ar 1 and Ar 2 or Ar 3 and Ar 4 may be independently linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without an aromatic ring or a heteroaromatic ring to form a fused ring, and the carbon atom of the alkylene may be further substituted by NR 21 , O, S or SiR 22 R 23 ;
  • R 1 through R 6 and R 11 through R 13 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, (C6-C30)aryl, (C2-C30)heteroaryl, (C1-C30)alkoxy, (C6-C60)aryloxy, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, (C6-C30)aryl(C1-C30)alkylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl or tri(C6-C30)arylsilyl;
  • R 21 through R 23 independently represent (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, adamantyl, halogen, cyano, (C6-C30)aryl, (C2-C30)heteroaryl, tri(C1-C30) alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl or tri(C6-C30)arylsilyl, or R 22 and R 23 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring; and
  • the alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylamino, arylamino, arylalkylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R 1 through R 6 ; the aryl, heteroaryl, heterocycloalkyl, cycloalkyl, adamantyl or bicycloalkyl of Ar 1 through Ar 4 ; the fused ring formed by the linkage of each of Ar 1 and Ar 2 or Ar 3 and Ar 4 ; and the alkyl, haloalkyl, alkoxy, morpholino, thiomorpholino, piperidino, heterocycloalkyl, cycloalkyl, adamantyl, aryl, heteroaryl, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R 21 through R 23 may be further substituted by one or more substituent(s) selected
  • alkyl alkoxy and other substituents containing “alkyl” moiety include both linear and branched species.
  • 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.
  • the heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a 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
  • the alkyl moiety of "(C1-C30)alkyl, (C1-C30)alkoxy, mono or di(C1-C30)alkylamino, (C6-C30)aryl(C1-C30)alkylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, halo(C1-C30)alkyl, (C1-C30)alkylthio, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl" or the like may have 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms.
  • the aryl moiety of "(C6-C30)aryl, mono or di(C6-C30)arylamino, (C6-C30)aryl(C1-C30)alkylamino, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl" or the like may have 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms.
  • the heteroaryl of "(C3-C30)heteroaryl” may have 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms.
  • the cycloalkyl of "(C3-C30)cycloalkyl” may have 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms.
  • the alkylene or alkenylene of "(C3-C30)alkylene or alkenylene” may have 3 to 20 carbon atoms, more specifically 3 to 10 carbon atoms.
  • organic electroluminescent compound according to the present invention may include compounds represented by Chemical Formula 2 below.
  • R 5 and R 6 independently represent hydrogen, (C6-C30)aryl or (C2-C30)heteroaryl;
  • Ar 1 through Ar 4 independently represent (C6-C30)aryl, (C2-C30)heteroaryl containing one or more heteroatom(s) selected from N, O and S, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, adamantyl, (C7-C30)bicycloalkyl or , or Ar 1 and Ar 2 or Ar 3 and Ar 4 may be independently linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without an aromatic ring or a heteroaromatic ring to form a fused ring, and the carbon atom of the alkylene may be further substituted by NR 21 , O, S or SiR 22 R 23 ;
  • R 21 through R 23 independently represent (C1-C30)alkyl or (C6-C30)aryl, or R 22 and R 23 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring;
  • alkyl or aryl of R 21 through R 23 may be further substituted by one or more substituent(s) selected from the group consisting of (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, (C1-C30)alkylthio, piperidino, morpholino, thiomorpholino, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, halogen, cyano, nitro, hydroxyl, (C6-C30)aryl
  • Ar 1 and Ar 2 and Ar 3 and Ar 4 are independently linked via alkylene or alkenylene are independently selected from following structures, but are not limited thereto:
  • R 21 through R 25 independently represent (C1-C30)alkyl or (C6-C30)aryl.
  • Ar 1 through Ar 4 are independently selected from following structures, but are not limited thereto:
  • organic electroluminescent compound according to the present invention may be specifically exemplified as following compounds but the present invention is not limited thereto:
  • organic electroluminescent compound according to the present invention may be prepared as shown in Scheme 1 below but is not limited thereto.
  • Ar 1 through Ar 4 and R 1 through R 6 are the same as defined in Chemical Formula 1.
  • an organic electroluminescent device which comprises 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 organic electroluminescent compound(s) of Chemical Formula 1.
  • the organic layer comprises an electroluminescent layer including one or more host(s) when one or more organic electroluminescent compounds of Chemical Formula 1 are used as the electroluminescent dopant.
  • 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 4 below.
  • a specific structure of the host compound of Chemical Formula 3 or 4 below is exemplified in Paragraphs ⁇ 162> to ⁇ 210> of KR Patent Application No. 10-2008-0060393 but is not limited thereto.
  • L 1 represents (C6-C30)arylene or (C4-C30)heteroarylene
  • L 2 represents anthracenylene
  • Ar 11 through Ar 14 independently represent hydrogen, deuterium, (C1-C30)alkyl, (C1-C30)alkoxy, halogen, (C4-C30)heteroaryl, (C5-C30)cycloalkyl or (C6-C30)aryl, and the cycloalkyl, aryl or heteroaryl of Ar 11 through Ar 14 may be further substituted by one or more substituent(s) selected from the group consisting of (C6-C30)aryl or (C4-C30)heteroaryl with or without one or more substituent(s) selected from the group consisting of deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, (C3-C30)cycloalkyl, halogen, cyano, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)aryl
  • a, b, c and d independently represent an integer from 0 to 4.
  • the electroluminescent layer means the layer where electroluminescence occurs, and it may be a single layer or a multi-layer that two or more layers are laminated.
  • 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 3 or 4 is selected as an electroluminescent host, it may considerably compensate for the electrical disadvantage of the organic electroluminescent compound represented by Chemical Formula 1 according to the present invention.
  • the organic electroluminescent device may comprise the organic electroluminescent compound of Chemical Formula 1 and may comprise one or more compound(s) selected from the group consisting of arylamine or styrylamine compounds.
  • arylamine or styrylamine compounds are provided in Paragraph Nos. ⁇ 212> to ⁇ 224> of KR Patent Application No. 10-2008-0060393 but are not limited thereto.
  • the organic layer may further comprise one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements in addition to the organic electroluminescent compound of Chemical Formula 1.
  • the organic layer may comprise 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 is taken as a subpixel and one or more subpixel(s) including one or more metal compound(s) selected from the 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, red or green 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 (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 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. Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
  • the organic electroluminescent compound according to the present invention exhibits good luminous efficiency in blue color and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
  • Organic electroluminescent Compounds 1 to 67 were prepared according to Preparation Example 1.
  • Table 1 shows 1 H NMR and MS/FAB of the prepared organic electroluminescent compounds.
  • An OLED device was manufactured using the electroluminescent material according to the present invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) 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 vapor-deposited on the formed layers.
  • DNA (Examples 1 to 3) of a following structure was placed in one cell of the vacuum vapor deposition apparatus and the compound according to the present invention was placed in another cell. Then, an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer at a deposition rate of 100:3.
  • Each compound used in the OLED device as an electroluminescent material was purified by vacuum sublimation at 10 -6 torr.
  • the luminous efficiencies of the OLED comprising the organic electroluminescent compounds according to the present invention in the Examples 1-3 were measured at 1,000 cd/m 2 , respectively, and the results are shown in Table 2.
  • the organic electroluminescent compounds of the present invention provide deep blue color. That, when a blue color is required for realizing the color close to the NTSC standard in the organic electroluminescent display, the organic electroluminescent compounds of the present invention may be useful. Since phenanthrene derivatives have high glass transition temperature, superior thermal stability is acquired. As described above, the organic electroluminescent compound of the present invention is used as a blue light-emitting material having high purity.
  • the organic electroluminescent compound according to the present invention exhibits good luminous efficiency in blue color and excellent life property, it may be used to manufacture OLED devices having very superior operation life.

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Abstract

Provided are novel organic electroluminescent compounds and an organic electroluminescent device using the same. Since the organic electroluminescent compound exhibits high luminous efficiency in blue color and excellent life property, it may be used to manufacture OLEDs having very superior operation life.

Description

NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
The present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same, more particularly, to novel organic electroluminescent compounds used as a blue electroluminescent 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 are generally classified into high-molecular materials and low-molecular materials. The low-molecular materials include metal complexes and thoroughly organic electroluminescent materials which do not contain metal, from the aspect of molecular structure. Such electroluminescent materials include chelate complexes such as tris(8-quinolinolato)aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bis(styrylarylene) derivatives and oxadiazole derivatives. From those materials, it is reported that light emission of visible region from blue to red can be obtained and it is expected that a color display device will be realized.
In the meanwhile, for conventional blue materials, a number of materials have been developed and commercialized since the development of diphenylvinyl-biphenyl (DPVBi) (Compound a) by Idemitsu-Kosan. In addition to the blue material system from Idemitsu-Kosan, dinaphthylanthracene (DNA) (Compound b) of Kodac, tetra(t-butyl)perylene (Compound c) system or the like have been known. However, extensive research and development should be performed with respect to these materials.
The distryl compound system of Idemitsu-Kosan, which is known to have highest efficiency up to now, has 6 lm/W power efficiency and beneficial device lifetime of more than 30,000 hr. However, when it is applied to a full-colored display, the lifetime is merely several thousand hours, owing to decrease of color purity over operation time. In case of blue electroluminescence, it becomes advantageous from the aspect of the luminous efficiency, if the electroluminescent wavelength is shifted a little toward longer wavelength. However, it is not easy to apply the material to a display of high quality because of unsatisfactory color purity in blue. Furthermore, the research and development of such materials are urgent because of the problems in color purity, efficiency and thermal stability.
Figure PCTKR2011002526-appb-I000001
With intensive efforts to overcome the problems of conventional techniques as described above, the present inventors have invented novel organic electroluminescent compounds which realize organic electroluminescent devices having excellent luminous efficiency and noticeably improved life property. The object of the present invention is to provide organic electroluminescent compounds having the backbone with appropriate color coordinates to provide better luminous efficiency and device life compared with conventional dopant material, while overcoming the problems described above, and a highly efficient and long life organic electroluminescent device using the organic electroluminescent compounds.
Provided are novel organic electroluminescent compounds and an organic electroluminescent device using the same. The organic electroluminescent compound is a compound represented by Chemical Formula 1. With superior luminescence efficiency in blue color 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.
[Chemical Formula 1]
Figure PCTKR2011002526-appb-I000002
wherein
Ar1 through Ar4 independently represent (C6-C30)aryl, (C2-C30)heteroaryl containing one or more heteroatom(s) selected from N, O and S, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, adamantyl, (C7-C30)bicycloalkyl or
Figure PCTKR2011002526-appb-I000003
, or Ar1 and Ar2 or Ar3 and Ar4 may be independently linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without an aromatic ring or a heteroaromatic ring to form a fused ring, and the carbon atom of the alkylene may be further substituted by NR21, O, S or SiR22R23;
R1 through R6 and R11 through R13 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, (C6-C30)aryl, (C2-C30)heteroaryl, (C1-C30)alkoxy, (C6-C60)aryloxy, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, (C6-C30)aryl(C1-C30)alkylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl or tri(C6-C30)arylsilyl;
R21 through R23 independently represent (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, adamantyl, halogen, cyano, (C6-C30)aryl, (C2-C30)heteroaryl, tri(C1-C30) alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl or tri(C6-C30)arylsilyl, or R22 and R23 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring; and
the alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylamino, arylamino, arylalkylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R1 through R6; the aryl, heteroaryl, heterocycloalkyl, cycloalkyl, adamantyl or bicycloalkyl of Ar1 through Ar4; the fused ring formed by the linkage of each of Ar1 and Ar2 or Ar3 and Ar4; and the alkyl, haloalkyl, alkoxy, morpholino, thiomorpholino, piperidino, heterocycloalkyl, cycloalkyl, adamantyl, aryl, heteroaryl, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R21 through R23 may be further substituted by one or more substituent(s) selected from the group consisting of (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, (C1-C30)alkylthio, piperidino, morpholino, thiomorpholino, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, halogen, cyano, nitro, hydroxyl, (C6-C30)aryl, (C6-C30)aryloxy, (C6-C30)arylthio, (C2-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl.
In the present invention, "alkyl", "alkoxy" and other substituents containing "alkyl" moiety include both linear and branched species. 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. 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 B, N, O, S, P(=O), Si and Se 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.
The heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a 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, quinolizinyl, quinoxalinyl, carbazolyl, phenanthridinyl, benzodioxolyl, etc., an N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide, etc.), a quaternary salt thereof, etc., but are not limited thereto.
In the present invention, the alkyl moiety of "(C1-C30)alkyl, (C1-C30)alkoxy, mono or di(C1-C30)alkylamino, (C6-C30)aryl(C1-C30)alkylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, halo(C1-C30)alkyl, (C1-C30)alkylthio, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl" or the like may have 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms. The aryl moiety of "(C6-C30)aryl, mono or di(C6-C30)arylamino, (C6-C30)aryl(C1-C30)alkylamino, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl" or the like may have 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms. The heteroaryl of "(C3-C30)heteroaryl" may have 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms. The cycloalkyl of "(C3-C30)cycloalkyl" may have 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms. The alkylene or alkenylene of "(C3-C30)alkylene or alkenylene" may have 3 to 20 carbon atoms, more specifically 3 to 10 carbon atoms.
Also, the organic electroluminescent compound according to the present invention may include compounds represented by Chemical Formula 2 below.
[Chemical Formula 2]
Figure PCTKR2011002526-appb-I000004
wherein
R5 and R6 independently represent hydrogen, (C6-C30)aryl or (C2-C30)heteroaryl;
Ar1 through Ar4 independently represent (C6-C30)aryl, (C2-C30)heteroaryl containing one or more heteroatom(s) selected from N, O and S, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, adamantyl, (C7-C30)bicycloalkyl or
Figure PCTKR2011002526-appb-I000005
, or Ar1 and Ar2 or Ar3 and Ar4 may be independently linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without an aromatic ring or a heteroaromatic ring to form a fused ring, and the carbon atom of the alkylene may be further substituted by NR21, O, S or SiR22R23;
R21 through R23 independently represent (C1-C30)alkyl or (C6-C30)aryl, or R22 and R23 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring; and
the aryl or heteroaryl of R5 and R6; the aryl, heteroaryl, heterocycloalkyl, cycloalkyl, adamantyl or bicycloalkyl of Ar1 through Ar4; the fused ring formed by the linkage of each of Ar1 and Ar2 or Ar3 and Ar4; and alkyl or aryl of R21 through R23 may be further substituted by one or more substituent(s) selected from the group consisting of (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, (C1-C30)alkylthio, piperidino, morpholino, thiomorpholino, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, halogen, cyano, nitro, hydroxyl, (C6-C30)aryl, (C6-C30)aryloxy, (C6-C30)arylthio, (C2-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl.
Also,
Figure PCTKR2011002526-appb-I000006
and
Figure PCTKR2011002526-appb-I000007
formed as the Ar1 and Ar2 and Ar3 and Ar4 are independently linked via alkylene or alkenylene are independently selected from following structures, but are not limited thereto:
Figure PCTKR2011002526-appb-I000008
wherein
R21 through R25 independently represent (C1-C30)alkyl or (C6-C30)aryl.
More specifically, the Ar1 through Ar4 are independently selected from following structures, but are not limited thereto:
Figure PCTKR2011002526-appb-I000009
Figure PCTKR2011002526-appb-I000010
Figure PCTKR2011002526-appb-I000011
Figure PCTKR2011002526-appb-I000012
Figure PCTKR2011002526-appb-I000013
Figure PCTKR2011002526-appb-I000014
Figure PCTKR2011002526-appb-I000015
Figure PCTKR2011002526-appb-I000016
Figure PCTKR2011002526-appb-I000017
Figure PCTKR2011002526-appb-I000018
Figure PCTKR2011002526-appb-I000019
The organic electroluminescent compound according to the present invention may be specifically exemplified as following compounds but the present invention is not limited thereto:
Figure PCTKR2011002526-appb-I000020
Figure PCTKR2011002526-appb-I000021
Figure PCTKR2011002526-appb-I000022
Figure PCTKR2011002526-appb-I000023
Figure PCTKR2011002526-appb-I000024
Figure PCTKR2011002526-appb-I000025
Figure PCTKR2011002526-appb-I000026
Figure PCTKR2011002526-appb-I000027
Figure PCTKR2011002526-appb-I000028
Figure PCTKR2011002526-appb-I000029
Figure PCTKR2011002526-appb-I000030
Figure PCTKR2011002526-appb-I000031
Figure PCTKR2011002526-appb-I000032
Figure PCTKR2011002526-appb-I000033
Figure PCTKR2011002526-appb-I000034
Figure PCTKR2011002526-appb-I000035
Figure PCTKR2011002526-appb-I000036
Figure PCTKR2011002526-appb-I000037
Figure PCTKR2011002526-appb-I000038
The organic electroluminescent compound according to the present invention may be prepared as shown in Scheme 1 below but is not limited thereto.
[Scheme 1]
Figure PCTKR2011002526-appb-I000039
wherein
Ar1 through Ar4 and R1 through R6 are the same as defined in Chemical Formula 1.
Provided is an organic electroluminescent device, which comprises 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 organic electroluminescent compound(s) of Chemical Formula 1.
In the organic electroluminescent device, the organic layer comprises an electroluminescent layer including one or more host(s) when one or more organic electroluminescent compounds of Chemical Formula 1 are used as the electroluminescent dopant. 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 4 below. A specific structure of the host compound of Chemical Formula 3 or 4 below is exemplified in Paragraphs <162> to <210> of KR Patent Application No. 10-2008-0060393 but is not limited thereto.
[Chemical Formula 3]
(Ar11)a-L1-(Ar12)b
[Chemical Formula 4]
(Ar13)c-L2-(Ar14)d
wherein
L1 represents (C6-C30)arylene or (C4-C30)heteroarylene;
L2 represents anthracenylene;
Ar11 through Ar14 independently represent hydrogen, deuterium, (C1-C30)alkyl, (C1-C30)alkoxy, halogen, (C4-C30)heteroaryl, (C5-C30)cycloalkyl or (C6-C30)aryl, and the cycloalkyl, aryl or heteroaryl of Ar11 through Ar14 may be further substituted by one or more substituent(s) selected from the group consisting of (C6-C30)aryl or (C4-C30)heteroaryl with or without one or more substituent(s) selected from the group consisting of deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, (C3-C30)cycloalkyl, halogen, cyano, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl, deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, (C3-C30)cycloalkyl, halogen, cyano, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl; and
a, b, c and d independently represent an integer from 0 to 4.
The electroluminescent layer means the layer where electroluminescence occurs, and it may be a single layer or a multi-layer that two or more layers are laminated. When a mixture of host-dopant is used according to the constitution of the present invention, noticeable improvement in luminous efficiency by the electroluminescent host may be confirmed. 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 3 or 4 is selected as an electroluminescent host, it may considerably compensate for the electrical disadvantage of the organic electroluminescent compound represented by Chemical Formula 1 according to the present invention.
The organic electroluminescent device may comprise the organic electroluminescent compound of Chemical Formula 1 and may comprise one or more compound(s) selected from the group consisting of arylamine or styrylamine compounds. Specific examples of arylamine or styrylamine compounds are provided in Paragraph Nos. <212> to <224> of KR Patent Application No. 10-2008-0060393 but are not limited thereto.
Also, in the organic electroluminescent device according to the present invention, the organic layer may further comprise one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements in addition to the organic electroluminescent compound of Chemical Formula 1. The organic layer may comprise 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 is taken as a subpixel and one or more subpixel(s) including one or more metal compound(s) selected from the 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, red or green 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. Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency in blue color and excellent life property, it may be used to manufacture OLED devices 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 68
Figure PCTKR2011002526-appb-I000040
Preparation of Compound B
Compound A (20 g, 96.05 mmol), benzoyl peroxide (3.1 g, 9.60 mmol, 75%), nitrobenzene (300 mL) and Br2 (10.85 mL, 211.3 mmol) were mixed at room temperature and heated at 120℃. 3 hours later, the mixture was cooled to room temperature, neutralized with KOH solution and extracted with methylene chloride (MC). After distillation under reduced pressure, Compound B (20 g, 56.92 %) was obtained by recrystallizing an obtained solid with ethyl acetate (EA).
Preparation of Compound C
2-bromonaphthalene (25.4 g, 122.95 mmol) was dissolved in THF (1000 mL) and n-buLi (114.7 mmol, 2.5M in hexane) was slowly added at -78℃. 30 minutes later, the mixture was stirred at room temperature. 30 minutes later, Compound B (14.1 g, 40 mmol) was added to the mixture. The mixture was stirred for 12 hours and extracted with distilled water and MC. After drying an organic layer with MgSO4 and removing the solvent via distillation under reduced pressure, Compound C (10 g, 40 %) was obtained by column separation (MC:Hex=1:1).
Preparation of Compound D
Compound C (10g, 16.06 mmol) was added to acetic acid (500 mL) and the mixture was heated to 130℃. Zn (20.2 g) was slowly added to the mixture and then HCl (20 mL) was slowly added thereto. 30 minutes later, Zn (10 g) was added to the mixture and then HCl (10 mL) was further added thereto. After stirring the mixture for 12 hours under reflux, the mixture was cooled to room temperature. A produced solid was filtered under reduced pressure by adding distilled water. The obtained solid was washed with NaOH solution and purified by column separation to obtain Compound D (6.5 g, 11.04 mmol, 68.74 %).
Preparation of Compound 68
Compound D (5 g, 8.49 mmol), diphenylamine (3.7 g, 22.09 mmol), Pd(OAc)2 (0.09 g, 0.42 mmol), and NaOt-bu (3.26 g, 33.99 mmol) were added. Toluene (200 mL) and P(t-bu)3 (0.50 mL, 1.019 mmol, 50% in xylene) were added to the mixture at nitrogen atmosphere. The mixture was stirred under reflux. After stirring the mixture for 12 hours, the mixture was cooled to room temperature and extracted with distilled water and MC. After drying an organic layer with MgSO4 and removing the solvent via distillation under reduced pressure, Compound 68 (2.9 g, 75.8 %) was obtained via purification by column separation.
1H NMR (CDCl3, 200MHz): d = 6.63(8H, m), 6.81(4H, m), 7.02(2H, m), 7.2(8H, m), 7.58~7.59(6H, m), 7.73(2H, m), 7.87~7.92(4H, m), 8(4H, m), 8.13(2H, m). MS/FAB: 764.96(found), 764.32(calculated).
Organic electroluminescent Compounds 1 to 67 were prepared according to Preparation Example 1. Table 1 shows 1H NMR and MS/FAB of the prepared organic electroluminescent compounds.
Table 1
Comp. 1H NMR(CDCl3, 200 MHz) MS/FAB
found calculated
1 δ= 2.34(6H, s), 6.63(8H, m), 6.81(4H, m), 7.02(2H, m), 7.2(8H, m), 7.29~7.33(8H, m), 7.87(2H, m), 8.13(2H, m) 692.89 692.32
2 δ= 1.69(24H, s), 6.05(4H, s), 7.02(2H, m), 7.22~7.3(24H, m), 7.58~7.59(6H, m), 7.73(2H, m), 7.87~7.92(4H, m), 8(4H, m), 8.13(2H, m) 1180.57 1181.55
3 δ= 6.63~6.68(6H, m), 6.81(2H, m), 7~7.02(4H, m), 7.2(4H, m), 7.3(4H, m), 7.39(4H, m), 7.87~7.88(4H, m), 8.13(2H, m) 680.74 680.23
4 δ= 6.68(4H, m), 7~7.02(6H, m), 7.58~7.59(6H, m), 7.73(2H, m), 7.87~7.92(8H, m), 8(4H, m), 8.13(2H, m) 724.80 724.24
5 δ= 6.01(4H, m), 6.72(4H, m), 6.84(4H, m), 7.02(2H, m), 7.17(2H, m), 7.4(2H, m), 7.69(2H, m), 7.87(2H, m), 8.13(2H, m) 701.00 700.03
6 δ= 2.34(6H, s), 7.02(2H, m), 7.14(4H, m), 7.29~7.38(16H, m), 7.66(4H, m), 7.87~7.89(6H, m), 8.13(2H, m) 852.97 852.30
7 δ= 6.34(4H, m), 7.02(2H, m), 7.5~7.52(8H, m), 7.71(2H, m), 7.79(4H, m), 7.87(2H, m), 7.98(4H, m), 8.13(2H, m) 736.99 736.11
8 δ= 2.34(6H, s), 6.63(4H, m), 6.81(2H, m), 7.02(2H, m), 7.2(4H, m), 7.29~7.33(8H, m), 7.53(4H, m), 7.87(2H, m), 8.01(2H, m), 8.13~8.18(4H, m) 807.04 806.25
9 δ= 7.02(2H, m), 7.25(8H, m), 7.53~7.59(14H, m), 7.73(2H, m), 7.87~7.92(4H, m), 8~8.01(8H, m), 8.13~8.18(6H, m) 1145.44 1145.25
10 δ= 7.02(2H, m), 7.3(4H, m), 7.39(12H, m), 7.74(8H, m), 7.87(2H, m), 8.13(2H, m) 864.85 864.23
11 δ= 3.47(6H, s), 6.63(4H, m), 6.81(2H, m), 7.02(2H, m), 7.1(2H, m), 7.2~7.25(16H, m), 7.58~7.59(8H, m), 7.73(2H, m), 7.87~7.92(4H, m), 8(4H, m), 8.13(2H, m) 1025.24 1024.43
12 δ= 1.16(8H, m), 1.48(4H, m), 1.58(8H, m), 2.34(6H, s), 2.57(2H, m), 6.77(2H, m), 6.99(2H, m), 7.23~7.33(16H, m), 7.9(2H, m), 8.1(2H, m) 704.98 704.41
13 δ= 1.16(16H, m), 1.48(8H, m), 1.58(16H, m), 2.34(6H, s), 2.57(4H, m), 7.15(2H, m), 7.29~7.33(8H, m), 7.94(2H, m), 8.26(2H, m) 717.08 716.51
14 δ= 1.71(12H, m), 2.14~2.18(18H, m), 6.77(2H, m), 6.99(2H, m), 7.23(4H, m), 7.3~7.39(12H, m), 7.9(2H, m), 8.1(2H, m) 817.06 816.43
15 δ= 1.71(24H, m), 2.14~2.18(36H, m), 7.15~7.17(4H, m), 7.4(2H, m), 7.69(2H, m), 7.94(2H, m), 8.26(2H, m) 909.38 908.51
16 δ= 5.19(8H, s), 6.39(4H, m), 6.51(4H, m), 7.02~7.06(22H, m), 7.15(16H, m), 7.25(8H, m), 7.58~7.59(6H, m), 7.73(2H, m), 7.87~7.92(4H, m), 8(4H, m), 8.13(2H, m) 1622.00 1620.63
17 δ= 1.35(18H, s), 3.83(6H, s), 6.55(4H, m), 6.63(4H, m), 6.81(2H, m), 7.01~7.05(10H, m), 7.2(4H, m), 7.68(4H, m), 7.87(2H, m), 8.13(2H, m) 837.10 836.43
18 δ= 0.25(18H, s), 2.34(6H, s), 6.61~6.63(8H, m), 6.81(2H, m), 7.02(2H, m), 7.15~7.2(8H, m), 7.29~7.33(8H, m), 7.87(2H, m), 8.13(2H, m) 837.25 836.40
19 δ= 6.73(8H, m), 7.02(2H, m), 7.21(8H, m), 7.3(4H, m), 7.37~7.39(28H, m), 7.46(24H, m), 7.55(12H, m), 7.87(2H, m), 8.13(2H, m) 1734.37 1732.61
20 δ= 3.83(6H, s), 6.61(8H, m), 6.99~7.05(14H, m), 7.68(4H, m), 7.87(2H, m), 8.13(2H, m) 796.85 796.27
21 δ= 6.61(8H, m), 6.99~7.02(10H, m), 7.25(8H, m), 7.58~7.59(6H, m), 7.73(2H, m), 7.87~7.92(4H, m), 8(4H, m), 8.13(2H, m) 989.11 988.34
22 δ= 6.81(8H, m), 7.02(2H, m), 7.39(8H, m), 7.71(2H, m), 7.87(2H, m), 8.13(2H, m) 612.68 612.21
23 δ= 2.34(6H, s), 3.83(12H, s), 6.52(8H, m), 6.74(8H, m), 7.02(2H, m), 7.29~7.33(8H, m), 7.87(2H, m), 8.13(2H, m) 812.99 812.36
24 δ= 2.34(6H, s), 6.63(4H, m), 6.81(2H, m), 7.02(2H, m), 7.2(4H, m), 7.29~7.36(10H, m), 7.49~7.5(4H, m), 7.74~7.77(4H, m), 7.84~7.88(6H, m), 8.13(2H, m) 793.00 792.35
25 δ= 6.63(4H, m), 6.81(2H, m), 7.02(2H, m), 7.17~7.2(6H, m), 7.36~7.4(4H, m), 7.49~7.5(4H, m), 7.69~7.77(6H, m), 7.84~7.88(6H, m), 8.13(2H, m) 777.01 776.23
26 δ= 2.34(6H, s), 6.63(4H, m), 6.81(2H, m), 7.02(4H, m), 7.2(4H, m), 7.29~7.33(8H, m), 7.71(4H, m), 7.82~7.88(8H, m), 8.12~8.13(6H, m), 8.93(2H, m) 893.12 892.38
27 δ= 6.63(4H, m), 6.81(2H, m), 6.91(2H, m), 7.02(2H, m), 7.17~7.2(6H, m), 7.4(2H, m), 7.69(2H, m), 7.82~7.88(10H, m), 8.12~8.13(6H, m), 8.93(4H, m) 877.12 876.26
28 δ= 6.63(4H, m), 6.81(2H, m), 6.91(2H, s), 7.02(2H, m), 7.2(4H, m), 7.71(2H, m), 7.82~7.88(12H, m), 8.12~8.13(6H, m), 8.93(6H, m) 812.99 812.32
29 δ= 6.63(4H, m), 6.81(2H, m), 6.91(2H, s), 7.02(2H, m), 7.17~7.2(6H, m), 7.4(2H, m), 7.69(2H, m), 7.82~7.88(12H, m), 8.12~8.13(6H, m), 8.93(6H, m) 977.24 976.29
30 δ= 3.83(6H, s), 6.63(4H, m), 6.81(2H, m), 7.02~7.05(6H, m), 7.2(8H, m), 7.68~7.71(12H, m), 7.82~7.87(4H, m), 8(4H, m), 8.13(2H, m) 973.16 972.37
31 δ= 2.34(6H, s), 6.63(4H, m), 6.81(2H, m), 7.02(4H, m), 7.2(4H, m), 7.29~7.33(8H, m), 7.85~7.87(12H, m), 8.13(4H, m), 8.52(8H, m) 993.24 992.41
32 δ= 6.63(4H, m), 6.81(4H, m), 7.02(2H, m), 7.2(4H, m), 7.3(4H, m), 7.39(4H, m), 7.57(2H, m), 7.73~7.78(4H, m), 7.87~7.88(4H, m), 8.1~8.13(6H, m), 8.42(4H, m) 949.09 948.33
33 δ= 3.83(6H, s), 6.62~6.63(6H, m), 6.81(2H, m), 7.02~7.05(6H, m), 7.2(4H, m), 7.39(12H, m), 7.68(4H, m), 7.74(2H, m), 7.87~7.91(8H, m), 8.13(2H, m) 1073.28 1072.40
34 δ= 6.63(4H, m), 6.81(2H, m), 7.02(2H, m), 7.17~7.2(6H, m), 7.4(2H, m), 7.57~7.58(6H, m), 7.69(2H, m), 7.87(2H, m), 7.94(2H, m), 8.13(2H, m), 8.22(2H, m), 8.38(2H, m), 8.83(2H, m) 881.08 880.24
35 δ= 3.83(6H, s), 6.63(4H, m), 6.69(4H, m), 6.81(2H, m), 7.02~7.05(6H, m), 7.2(4H, m), 7.41(2H, m), 7.51~7.54(12H, m), 7.68(4H, m), 7.87(2H, m), 8.13(2H, m) 877.08 876.37
36 δ= 0.9(12H, m), 1.91(8H, m), 6.63(4H, m), 6.69(4H, m), 6.81(2H, m), 7.02(2H, m), 7.2(4H, m), 7.28(2H, m), 7.38(2H, m), 7.54~7.55(6H, m), 7.63(2H, m), 7.71~7.77(4H, m), 7.87~7.93(6H, m), 8.13(2H, m) 953.26 952.48
37 δ= 0.9(12H, m), 1.91(8H, m), 6.58~6.63(6H, m), 6.75~6.81(4H, m), 7.02(2H, m), 7.2~7.28(14H, m), 7.38(2H, m), 7.55~7.62(10H, m), 7.73(2H, m), 7.87~7.92(6H, m), 8(4H, m), 8.13(2H, m) 1205.57 1204.57
38 δ= 0.9(24H, m), 1.91(16H, m), 6.58(4H, m), 6.75(4H, m), 7.02(2H, m), 7.28(4H, m), 7.38(4H, m), 7.55(4H, m), 7.62(4H, m), 7.71(2H, m), 7.87(6H, m), 8.13(2H, m) 1089.49 1088.60
39 δ= 0.9(48H, m), 1.91(32H, m), 6.64(4H, m), 6.81(4H, m), 7.02(2H, m), 7.28(4H, m), 7.38(4H, m), 7.55(4H, m), 7.69(4H, s), 7.71(2H, m), 7.77(4H, s), 7.84~7.87(10H, m), 8.13(2H, m) 1666.35 1664.98
40 δ= 2.34(6H, s), 5.19(8H, s), 6.39(4H, m), 6.51(4H, m), 7.02~7.06(22H, m), 7.15(16H, m), 7.29~7.33(8H, m), 7.87(2H, m), 8.13(2H, m) 1397.74 1396.57
41 δ= 6.58~6.63(6H, m), 6.75~6.81(4H, m), 7.02(2H, m), 7.11~7.26(32H, m), 7.55(2H, m), 7.62(2H, m), 7.69(2H, m), 7.87(4H, m), 8.13(2H, m) 1157.49 1156.39
42 δ= 3.83(6H, s), 6.58(4H, m), 6.75(4H, m), 7.02~7.05(6H, m), 7.11(16H, m), 7.26~7.38(32H, m), 7.55(4H, m), 7.62~7.68(8H, m), 7.87(6H, m), 8.13(2H, m) 1686.08 1684.68
43 δ= 6.58~6.63(6H, m), 6.75~6.81(4H, m), 7.02(2H, m), 7.16~7.2(12H, m), 7.28(2H, m), 7.35~7.38(6H, m), 7.55~7.62(10H, m), 7.73~7.75(6H, m), 7.87~7.92(6H, m), 8(4H, m), 8.13(2H, m) 1241.52 1240.48
44 δ= 6.39(2H, m), 6.55(2H, m), 6.63(4H, m), 6.81(2H, m), 7.02(2H, m), 7.16~7.2(24H, m), 7.31~7.35(14H, m), 7.5(2H, m), 7.71~7.75(8H, m), 7.87(2H, m), 8.13(2H, m) 1317.61 1316.51
45 δ= 6.48(4H, m), 6.65(4H, m), 7.02(2H, m), 7.17~7.22(14H, m), 7.28(12H, m), 7.4~7.45(14H, m), 7.56(4H, m), 7.69(2H, m), 7.81(12H, m), 7.87(2H, m), 8.13(2H, m) 1630.02 1628.51
46 δ= 6.58~6.63(6H, m), 6.75~6.81(8H, m), 7.02(2H, m), 7.17~7.2(6H, m), 7.28(2H, m), 7.38~7.4(4H, m), 7.48(4H, m), 7.55(2H, m), 7.62(2H, m), 7.69(2H, m), 7.87(4H, m), 8.13(2H, m), 8.51(4H, m) 1157.41 1156.34
47 δ= 1.51(8H, m), 2.09(8H, m), 3.83(6H, s), 6.58~6.63(6H, m), 6.75~6.81(4H, m), 7.02~7.05(6H, m), 7.2(4H, m), 7.28(2H, m), 7.38(2H, m), 7.55(2H, m), 7.62~7.68(6H, m), 7.87(4H, m), 8.13(2H, m) 1009.28 1008.47
48 δ= 1.51(8H, m), 2.11(8H, m), 6.63(4H, m), 6.77~6.81(4H, m), 7.02(2H, m), 7.18~7.24(8H, m), 7.44(2H, m), 7.61(2H, m), 7.73~7.75(4H, m), 7.87(2H, m), 7.99~8.02(6H, m), 8.09~8.13(4H, m), 8.75(4H, m) 1051.32 1050.47
49 δ= 1.48(12H, m), 2.02(8H, m), 3.83(6H, s), 6.58~6.63(6H, m), 6.75~6.81(4H, m), 7.02~7.05(6H, m), 7.2(4H, m), 7.28(2H, m), 7.38(2H, m), 7.55(2H, m), 7.62~7.68(6H, m), 7.87(4H, m), 8.13(2H, m) 1037.33 1036.50
50 δ= 1.48(24H, m), 2.02(16H, m), 6.58(4H, m), 6.75(4H, m), 7.02(2H, m), 7.28(4H, m), 7.38(4H, m), 7.55(4H, m), 7.62(4H, m), 7.71(2H, m), 7.87(6H, m), 8.13(2H, m) 1137.54 1136.60
51 δ= 2.34(6H, s), 3.49(8H, s), 6.58~6.63(6H, m), 6.75~6.81(4H, m), 7.02(2H, m), 7.2(12H, m), 7.28~7.38(12H, m), 7.55(2H, m), 7.62(2H, m), 7.87(4H, m), 8.13(2H, m) 1073.37 1072.48
52 δ= 3.49(16H, s), 6.58(4H, m), 6.75(4H, m), 7.02(2H, m), 7.2(16H, m), 7.28(4H, m), 7.38(4H, m), 7.53~7.55(8H, m), 7.62~7.66(8H, m), 7.87(6H, m), 8.13(2H, m) 1583.59 1580.42
53 δ= 6.62(4H, m), 6.7(4H, m), 7.02(2H, m), 7.55(4H, m), 7.87(2H, m), 7.99(4H, m), 8.07(4H, m), 8.13(2H, m), 8.75(4H, m) 670.76 670.26
54 δ= 2.34(6H, s), 6.62~6.63(6H, m), 6.7(2H, m), 6.81(2H, m), 7.02(2H, m), 7.2(4H, m), 7.29~7.33(8H, m), 7.55(2H, m), 7.87(2H, m), 8.07(2H, m), 8.13(2H, m) 694.86 694.31
55 δ= 7.02(2H, m), 7.25(8H, m), 7.37(4H, m), 7.57~7.59(10H, m), 7.69~7.75(10H, m), 7.87~8(12H, m), 8.13(2H, m), 8.22(4H, m) 1121.33 1120.43
56 δ= 6.63(4H, m), 6.81(2H, m), 7.02(2H, m), 7.2~7.25(12H, m), 7.37(2H, m), 7.57~7.59(8H, m), 7.69~7.75(6H, m), 7.87~8(10H, m), 8.13(2H, m), 8.22(2H, m) 1019.24 1018.40
57 δ= 6.62~6.63(6H, m), 6.81(2H, m), 7.02(2H, m), 7.19~7.2(6H, m), 7.4(4H, m), 7.71(2H, m), 7.8(2H, m), 7.87(2H, m), 8.13(2H, m), 8.75(2H, m) 614.74 614.25
58 δ= 7.25~7.39(14H, m), 7.5(2H, m), 7.63(2H, m), 7.8(2H, m), 7.94(2H, m), 8.1~8.12(4H, m), 8.55(2H, m), 8.9(2H, m) 696.78 696.24
59 δ= 1.72(12H, s), 6.55(4H, m), 6.73(4H, m), 7.02~7.05(10H, m), 7.71(2H, m), 7.87(2H, m), 8.13(2H, m) 592.77 592.29
60 δ= 6.38(8H, m), 6.56(8H, m), 6.63(4H, m), 6.81(2H, m), 7.02(2H, m), 7.2~7.25(12H, m), 7.58~7.59(6H, m), 7.73(2H, m), 7.87~7.92(4H, m), 8(4H, m), 8.13(2H, m) 1095.33 1094.43
61 δ= 2.34(6H, s), 6.59(4H, m), 6.77(4H, m), 6.89~6.92(8H, m), 7.02(2H, m), 7.29~7.33(8H, m), 7.87(2H, m), 8.13(2H, m) 720.85 720.28
62 δ= 2.34(6H, s), 6.73(8H, m), 7.02(2H, m), 7.21(4H, m), 7.29~7.37(20H, m), 7.46(8H, m), 7.55(4H, m), 7.87(2H, m), 8.13(2H, m) 1053.44 1052.40
63 δ= 2.34(6H, s), 2.71(8H, s), 6.73(8H, m), 7.02(2H, m), 7.11~7.14(8H, m), 7.21(4H, m), 7.29~7.33(12H, m), 7.87(2H, m), 8.13(2H, m) 953.32 952.37
64 δ= 6.73(8H, m), 7.02(2H, m), 7.21(4H, m), 7.3(4H, m), 7.37(8H, m), 7.46(8H, m), 7.55(4H, m), 7.87(2H, m), 7.99(4H, m), 8.13(2H, m), 8.75(4H, m) 1027.37 1026.36
65 δ= 2.88(8H, m), 6.58(4H, m), 6.76(4H, m), 7.02~7.04(10H, m), 7.25(8H, m), 7.58~7.59(6H, m), 7.73(2H, m), 7.87~7.92(4H, m), 8(4H, m), 8.13(2H, m) 969.22 968.41
66 δ= 6.63(4H, m), 6.81(4H, m), 6.99~7.05(10H, m), 7.17(2H, m), 7.25(4H, m), 7.4(2H, m), 7.69(2H, m), 7.87(2H, m), 8.13(2H, m) 724.93 724.20
67 δ= 6.69(4H, m), 6.87(4H, m), 7.02(2H, m), 7.16(4H, m), 7.47(4H, m), 7.54(4H, m), 7.85~7.87(6H, m), 7.99(4H, m), 8.13(2H, m), 8.75(4H, m) 814.97 814.31
[Examples 1 to 3] 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(α-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.
After forming the hole injection layer and the hole transport layer, an electroluminescent layer was vapor-deposited on the formed layers. DNA (Examples 1 to 3) of a following structure was placed in one cell of the vacuum vapor deposition apparatus and the compound according to the present invention was placed in another cell. Then, an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer at a deposition rate of 100:3.
Figure PCTKR2011002526-appb-I000041
Subsequently, tris(8-hydroxyquinoline)-aluminum(III) (Alq) was vapor-deposited with a thickness of 20 nm as an electron transport layer on the electroluminescent layer. Then, after vapor-depositing lithium quinolate (Liq) with a thickness of 1 to 2 nm as an electron injection layer, an Al cathode having a thickness of 150 nm was formed using another vacuum vapor deposition apparatus to manufacture an OLED.
Each compound used in the OLED device as an electroluminescent material was purified by vacuum sublimation at 10-6 torr.
The luminous efficiencies of the OLED comprising the organic electroluminescent compounds according to the present invention in the Examples 1-3 were measured at 1,000 cd/m2, respectively, and the results are shown in Table 2.
Table 2
No. EL material 1 EL material 2 Luminescence efficiency (cd/A) Color
Example 1 DNA Compound 68 3.3 Deep blue
2 DNA Compound 38 3.2 Deep blue
3 DNA Compound 57 3.0 Deep blue
As seen from Table 2, the organic electroluminescent compounds of the present invention provide deep blue color. That, when a blue color is required for realizing the color close to the NTSC standard in the organic electroluminescent display, the organic electroluminescent compounds of the present invention may be useful. Since phenanthrene derivatives have high glass transition temperature, superior thermal stability is acquired. As described above, the organic electroluminescent compound of the present invention is used as a blue light-emitting material having high purity.
Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency in blue color and excellent life property, it may be used to manufacture OLED devices having very superior operation life.

Claims (10)

  1. An organic electroluminescent compound represented by Chemical Formula 1:
    [Chemical Formula 1]
    Figure PCTKR2011002526-appb-I000042
    wherein
    Ar1 through Ar4 independently represent (C6-C30)aryl, (C2-C30)heteroaryl containing one or more heteroatom(s) selected from N, O and S, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, adamantyl, (C7-C30)bicycloalkyl or
    Figure PCTKR2011002526-appb-I000043
    , or Ar1 and Ar2 or Ar3 and Ar4 may be independently linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without an aromatic ring or a heteroaromatic ring to form a fused ring, and the carbon atom of the alkylene may be further substituted by NR21, O, S or SiR22R23;
    R1 through R6 and R11 through R13 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, (C6-C30)aryl, (C2-C30)heteroaryl, (C1-C30)alkoxy, (C6-C60)aryloxy, mono- or di(C1-C30)alkylamino, mono- or di(C6-C30)arylamino, (C6-C30)aryl(C1-C30)alkylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl or tri(C6-C30)arylsilyl;
    R21 through R23 independently represent (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, adamantyl, halogen, cyano, (C6-C30)aryl, (C2-C30)heteroaryl, tri(C1-C30) alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl or tri(C6-C30)arylsilyl, or R22 and R23 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring; and
    the alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, alkylamino, arylamino, arylalkylamino, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R1 through R6; the aryl, heteroaryl, heterocycloalkyl, cycloalkyl, adamantyl or bicycloalkyl of Ar1 through Ar4; the fused ring formed by the linkage of each of Ar1 and Ar2 or Ar3 and Ar4; and the alkyl, haloalkyl, alkoxy, morpholino, thiomorpholino, piperidino, heterocycloalkyl, cycloalkyl, adamantyl, aryl, heteroaryl, trialkylsilyl, dialkylarylsilyl or triarylsilyl of R21 through R23 may be further substituted by one or more substituent(s) selected from the group consisting of (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, (C1-C30)alkylthio, piperidino, morpholino, thiomorpholino, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, halogen, cyano, nitro, hydroxyl, (C6-C30)aryl, (C6-C30)aryloxy, (C6-C30)arylthio, (C2-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl.
  2. The organic electroluminescent compound according to claim 1, which is represented by Chemical Formula 2:
    [Chemical Formula 2]
    Figure PCTKR2011002526-appb-I000044
    wherein
    R5 and R6 independently represent hydrogen, (C6-C30)aryl or (C2-C30)heteroaryl;
    Ar1 through Ar4 independently represent (C6-C30)aryl, (C2-C30)heteroaryl containing one or more heteroatom(s) selected from N, O and S, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, adamantyl, (C7-C30)bicycloalkyl or
    Figure PCTKR2011002526-appb-I000045
    , or Ar1 and Ar2 or Ar3 and Ar4 may be independently linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without an aromatic ring or a heteroaromatic ring to form a fused ring, and the carbon atom of the alkylene may be further substituted by NR21, O, S or SiR22R23;
    R21 through R23 independently represent (C1-C30)alkyl or (C6-C30)aryl, or R22 and R23 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring; and
    the aryl or heteroaryl of R5 and R6; the aryl, heteroaryl, heterocycloalkyl, cycloalkyl, adamantyl or bicycloalkyl of Ar1 through Ar4; the fused ring formed by the linkage of each of Ar1 and Ar2 or Ar3 and Ar4; and alkyl or aryl of R21 through R23 may be further substituted by one or more substituent(s) selected from the group consisting of (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, (C1-C30)alkylthio, piperidino, morpholino, thiomorpholino, 5- to 7-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C3-C30)cycloalkyl, halogen, cyano, nitro, hydroxyl, (C6-C30)aryl, (C6-C30)aryloxy, (C6-C30)arylthio, (C2-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl.
  3. The organic electroluminescent compound according to claim 2, wherein
    Figure PCTKR2011002526-appb-I000046
    and
    Figure PCTKR2011002526-appb-I000047
    are independently selected from following structures:
    Figure PCTKR2011002526-appb-I000048
    wherein
    R21 through R25 independently represent (C1-C30)alkyl or (C6-C30)aryl.
  4. The organic electroluminescent compound according to claim 1, which is selected from the following compounds:
    Figure PCTKR2011002526-appb-I000049
    Figure PCTKR2011002526-appb-I000050
    Figure PCTKR2011002526-appb-I000051
    Figure PCTKR2011002526-appb-I000052
    Figure PCTKR2011002526-appb-I000053
    Figure PCTKR2011002526-appb-I000054
    Figure PCTKR2011002526-appb-I000055
    Figure PCTKR2011002526-appb-I000056
    Figure PCTKR2011002526-appb-I000057
    Figure PCTKR2011002526-appb-I000058
    Figure PCTKR2011002526-appb-I000059
    Figure PCTKR2011002526-appb-I000060
    Figure PCTKR2011002526-appb-I000061
    Figure PCTKR2011002526-appb-I000062
    Figure PCTKR2011002526-appb-I000063
    Figure PCTKR2011002526-appb-I000064
    Figure PCTKR2011002526-appb-I000065
    Figure PCTKR2011002526-appb-I000066
    Figure PCTKR2011002526-appb-I000067
  5. An organic electroluminescent device comprising the organic electroluminescent compound according to any of claims 1 to 4.
  6. The organic electroluminescent device according to claim 5, which comprises 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 organic electroluminescent compound(s) and one or more host compound(s) represented by Chemical Formula 3 or 4:
    [Chemical Formula 3]
    (Ar11)a-L1-(Ar12)b
    [Chemical Formula 4]
    (Ar13)c-L2-(Ar14)d
    wherein
    L1 represents (C6-C30)arylene or (C4-C30)heteroarylene;
    L2 represents anthracenylene;
    Ar11 through Ar14 independently represent hydrogen, deuterium, (C1-C30)alkyl, (C1-C30)alkoxy, halogen, (C4-C30)heteroaryl, (C5-C30)cycloalkyl or (C6-C30)aryl, and the cycloalkyl, aryl or heteroaryl of Ar11 through Ar14 may be further substituted by one or more substituent(s) selected from the group consisting of (C6-C30)aryl or (C4-C30)heteroaryl with or without one or more substituent(s) selected from the group consisting of deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, (C3-C30)cycloalkyl, halogen, cyano, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl, deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, (C3-C30)cycloalkyl, halogen, cyano, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl; and
    a, b, c and d independently represent an integer from 0 to 4.
  7. The organic electroluminescent device according to claim 6, wherein the organic layer further comprises one or more compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, or one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements.
  8. The organic electroluminescent device according to claim 6, which is a white-light emitting organic electroluminescent device wherein the organic layer comprises one or more organic electroluminescent layer(s) emitting blue, red or green light at the same time.
  9. The organic electroluminescent device according to claim 6, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
  10. The organic electroluminescent device according to claim 6, wherein a mixed region of a reductive dopant and an organic substance, or a mixed region of an oxidative dopant and an organic substance is placed on the inner surface of one or both electrode(s) among the pair of electrodes.
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