WO2011136482A1 - 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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WO2011136482A1
WO2011136482A1 PCT/KR2011/002489 KR2011002489W WO2011136482A1 WO 2011136482 A1 WO2011136482 A1 WO 2011136482A1 KR 2011002489 W KR2011002489 W KR 2011002489W WO 2011136482 A1 WO2011136482 A1 WO 2011136482A1
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alkyl
aryl
independently represent
heteroaryl
cycloalkyl
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PCT/KR2011/002489
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French (fr)
Inventor
Hyo Jung Lee
Young Jun Cho
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Publication of WO2011136482A1 publication Critical patent/WO2011136482A1/en

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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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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.
  • 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.
  • the alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R 1 through R 10 and R 31 through R 35 ; the arylene or heteroarylene of L 1 and L 2 ; the cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R 11 and R 12 ; and the fused ring formed by link between R 11 and R 12 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl;
  • n an integer 0, 1 or 2.
  • the alkyl moiety of "(C1-C30)alkyl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio" or the like may have 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms.
  • the aryl moiety of "(C6-C30)aryl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)aryloxy, (C6-C30)arylthio” 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 alkenyl or alkynyl of "(C2-C30)alkenyl or alkynyl” may have 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
  • alkyl includes linear or branched saturated monovalent hydrocarbon radical containing only carbon atoms and hydrogen atoms, or a combination thereof.
  • the "cycloalkyl” includes polycyclic hydrocarbon rings such as adamantyl or bicycloalkyl as well as a monocyclic ring.
  • 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, including a plurality of aryl groups having single bond(s) therebetween.
  • Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
  • the naphthyl includes 1-naphthyl and 2-naphthyl.
  • the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • the heteroaryl also includes heteroaryl groups having single bond(s) therebetween.
  • 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, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothi
  • organic electroluminescent compound according to the present invention includes compounds represented by Chemical Formula 2 or 3 below:
  • L 11 and L 12 independently represent (C6-C30)arylene, (C2-C30)heteroarylene or ;
  • L 21 and L 22 independently represent (C6-C30)arylene or (C2-C30)heteroarylene;
  • R 2 , R 3 , R 5 , R 6 , R 8 and R 9 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl or (C2-30)heteroaryl;
  • R 41 through R 44 independently represent (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl or , or may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring, and the carbon atom of the alkylene may be substituted by NR 21 , O or S, wherein R 21 represents hydrogen, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered heterocycloalkyl, (C3-C30)cycloalkyl, halogen, cyano, (C6-30)aryl, (C2-30)heteroaryl or R a R b R c Si- [wherein R
  • R 1 , R 4 , R 7 and R 10 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NR e R f [wherein R e and R f independently represent (C1-C30)alkyl or (C6-C30)aryl], R a R b R c Si- [wherein R a , R b and R c independently represent (C1-C30)alkyl or (C6-C30)aryl] or R d Y- [wherein Y represents O or S, and R d represents (C1-C30)alkyl or (C6-C30)aryl];
  • the alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R 1 through R 10 ; and the arylene or heteroarylene of L 11 , L 12 , L 21 and L 22 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl; and
  • n an integer 0, 1 or 2.
  • R 31 through R 35 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, phenyl, naphthyl, biphenyl, fluorenyl or phenanthryl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
  • L 21 and L 22 independently represent phenylene, naphthylene, anthracenylene, fluorenylene, phenanthrylene, biphenylene, triphenylene, fluoranthenylene, chrysenylene, pyrenylene, perylenylene, pyridinylene, furylene, thiophenylene, selenophenylene, pyrazinylene, pyridazinylene, quinolinylene or quinoxalinylene;
  • R 1 , R 4 , R 7 and R 10 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, triazinyl or pyrimidyl; and
  • the and may be independently selected from the following structures but are not limited thereto:
  • R 31 through R 35 independently represent (C1-C30)alkyl or (C6-C30)aryl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring.
  • organic electroluminescent compound according to the present invention may be prepared as shown in following Schemes 1 and 2 but are not limited thereto.
  • R 1 through R 10 , L 1 , L 2 , R 11 and R 12 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) represented by Chemical Formula 1.
  • the organic layer may include the electroluminescent layer, and the electroluminescent layer may further include one or more host(s) besides one or more organic electroluminescent compounds of Chemical Formula 1 as an electroluminescent dopant.
  • the host applied to the organic electroluminescent device of the present invention is not specifically limited but may be selected from following Chemical Formula 4 or 5.
  • L 101 represents (C6-C30)arylene or (C4-C30)heteroarylene;
  • L 102 represents anthracenylene
  • Ar 101 through Ar 104 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 101 through Ar 104 is 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 (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, (C3-C30)cycloalkyl, halogen, cyano, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C
  • 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 4 or 5 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 include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
  • the arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, 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 the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s).
  • 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 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 of Chemical Formula 1, 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.
  • 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 metal 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. 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.
  • the 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 111 were prepared according to the procedure of Preparation Examples 1 and 3. 1 H NMR and MS/FAB data of thus prepared organic electroluminescent compounds are given in Table 1.
  • 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 3) was placed in a cell of the vacuum vapor deposition apparatus as a host, and the compound according to the present invention was placed in another cell as a dopant.
  • the two materials were vapor-deposited at a rate of 100:3 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.
  • Luminescence efficiency of the OLED devices containing the organic electroluminescent compound according to the present invention manufactured in Examples 1 to 3 was measured at 1,000 cd/m 2 . The result is given in Table 2.
  • 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 good luminous efficiency in blue color and excellent life property of the material, it may be used to manufacture OLED devices 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 PCTKR2011002489-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 coordinate 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 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 PCTKR2011002489-appb-I000002
wherein
R1, R4, R7 and R10 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl], RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl], RdY- [wherein Y represents O or S, and Rd represents (C1-C30)alkyl or (C6-C30)aryl] or
Figure PCTKR2011002489-appb-I000003
, except for the case where two of R1, R4, R7 and R10 are hydrogen;
R2, R3, R5, R6, R8 and R9 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl], RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl] or RdY- [wherein Y represents O or S, and Rd represents (C1-C30)alkyl or (C6-C30)aryl];
L1 represents a single bond, (C6-C30)arylene or (C2-C30)heteroarylene;
L2 represents (C6-C30)arylene, (C2-C30)heteroarylene or
Figure PCTKR2011002489-appb-I000004
;
R11 and R12 independently represent (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl or
Figure PCTKR2011002489-appb-I000005
, or may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring, and the carbon atom of the alkylene may be substituted by NR21, O or S, wherein R21 represents hydrogen, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered heterocycloalkyl, (C3-C30)cycloalkyl, halogen, cyano, (C6-30)aryl, (C2-30)heteroaryl or RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl];
Z1 and Z2 independently represent -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Se- or -Si(R34)(R35);
R31 through R35 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl] or RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl], or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
the alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R1 through R10 and R31 through R35; the arylene or heteroarylene of L1 and L2; the cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R11 and R12; and the fused ring formed by link between R11 and R12 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl;
the heterocycloalkyl or heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P; and
m represents an integer 0, 1 or 2.
In the present invention, the alkyl moiety of "(C1-C30)alkyl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio" or the like may have 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms. The aryl moiety of "(C6-C30)aryl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)aryloxy, (C6-C30)arylthio" 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 alkenyl or alkynyl of "(C2-C30)alkenyl or alkynyl" may have 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
In the present invention, "alkyl" includes linear or branched saturated monovalent hydrocarbon radical containing only carbon atoms and hydrogen atoms, or a combination thereof. In the present invention, the "cycloalkyl" includes polycyclic hydrocarbon rings such as adamantyl or bicycloalkyl as well as a monocyclic ring.
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, including a plurality of aryl groups having single bond(s) therebetween. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto. The naphthyl includes 1-naphthyl and 2-naphthyl. The anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, and the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl. 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 P 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 also includes heteroaryl groups having single bond(s) therebetween.
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, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, 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.
Also, the organic electroluminescent compound according to the present invention includes compounds represented by Chemical Formula 2 or 3 below:
[Chemical Formula 2]
Figure PCTKR2011002489-appb-I000006
[Chemical Formula 3]
Figure PCTKR2011002489-appb-I000007
wherein
L11 and L12 independently represent (C6-C30)arylene, (C2-C30)heteroarylene or
Figure PCTKR2011002489-appb-I000008
;
L21 and L22 independently represent (C6-C30)arylene or (C2-C30)heteroarylene;
R2, R3, R5, R6, R8 and R9 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl or (C2-30)heteroaryl;
R41 through R44 independently represent (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl or
Figure PCTKR2011002489-appb-I000009
, or may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring, and the carbon atom of the alkylene may be substituted by NR21, O or S, wherein R21 represents hydrogen, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered heterocycloalkyl, (C3-C30)cycloalkyl, halogen, cyano, (C6-30)aryl, (C2-30)heteroaryl or RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl];
Z1 and Z2 independently represent -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Se- or -Si(R34)(R35);
R31 through R35 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl] or RaRbRcSi- [Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl], or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
R1, R4, R7 and R10 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl], RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl] or RdY- [wherein Y represents O or S, and Rd represents (C1-C30)alkyl or (C6-C30)aryl];
the alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R1 through R10; and the arylene or heteroarylene of L11, L12, L21 and L22 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl; and
m represents an integer 0, 1 or 2.
The L11 and L12 independently represent phenylene, naphthalene, biphenylene, phenanthrylene, pyrazinylene, triazinylene, quinolylene, phenanthrolinylene, thienylene, furylene, selenophenylene, thiadiazolylene, oxadiazolylene, selenadiazolylene or quinoxalinylene, or a divalent group selected from the following structures:
Figure PCTKR2011002489-appb-I000010
R31 through R35 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, phenyl, naphthyl, biphenyl, fluorenyl or phenanthryl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
L21 and L22 independently represent phenylene, naphthylene, anthracenylene, fluorenylene, phenanthrylene, biphenylene, triphenylene, fluoranthenylene, chrysenylene, pyrenylene, perylenylene, pyridinylene, furylene, thiophenylene, selenophenylene, pyrazinylene, pyridazinylene, quinolinylene or quinoxalinylene;
R2, R3, R5, R6, R8 and R9 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, triazinyl or pyrimidyl;
R41 through R44 independently represent cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, indenyl, fluorenyl, benzofluorenyl, spirobifluorenyl, anthracenyl, pyrenyl, phenanthryl, triphenylenyl, fluoranthenyl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, triazinyl, pyrimidyl or
Figure PCTKR2011002489-appb-I000011
;
R1, R4, R7 and R10 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, triazinyl or pyrimidyl; and
L11, L12, L21, L22, R1 through R10 and R41 through R44 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl, but are not limited thereto.
The
Figure PCTKR2011002489-appb-I000012
and
Figure PCTKR2011002489-appb-I000013
may be independently selected from the following structures but are not limited thereto:
Figure PCTKR2011002489-appb-I000014
wherein
R31 through R35 independently represent (C1-C30)alkyl or (C6-C30)aryl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring.
More specifically, the organic electroluminescent compound according to the present invention may be exemplified by following compounds but are not limited thereto:
Figure PCTKR2011002489-appb-I000015
Figure PCTKR2011002489-appb-I000016
Figure PCTKR2011002489-appb-I000017
Figure PCTKR2011002489-appb-I000018
Figure PCTKR2011002489-appb-I000019
Figure PCTKR2011002489-appb-I000020
Figure PCTKR2011002489-appb-I000021
Figure PCTKR2011002489-appb-I000022
Figure PCTKR2011002489-appb-I000023
Figure PCTKR2011002489-appb-I000024
Figure PCTKR2011002489-appb-I000025
Figure PCTKR2011002489-appb-I000026
Figure PCTKR2011002489-appb-I000027
Figure PCTKR2011002489-appb-I000028
Figure PCTKR2011002489-appb-I000029
Figure PCTKR2011002489-appb-I000030
Figure PCTKR2011002489-appb-I000031
Figure PCTKR2011002489-appb-I000032
Figure PCTKR2011002489-appb-I000033
Figure PCTKR2011002489-appb-I000034
Figure PCTKR2011002489-appb-I000035
Figure PCTKR2011002489-appb-I000036
Figure PCTKR2011002489-appb-I000037
Figure PCTKR2011002489-appb-I000038
Figure PCTKR2011002489-appb-I000039
Figure PCTKR2011002489-appb-I000040
Figure PCTKR2011002489-appb-I000041
Figure PCTKR2011002489-appb-I000042
Figure PCTKR2011002489-appb-I000043
Figure PCTKR2011002489-appb-I000044
Figure PCTKR2011002489-appb-I000045
Figure PCTKR2011002489-appb-I000046
Figure PCTKR2011002489-appb-I000047
Figure PCTKR2011002489-appb-I000048
Figure PCTKR2011002489-appb-I000049
Figure PCTKR2011002489-appb-I000050
Figure PCTKR2011002489-appb-I000051
Figure PCTKR2011002489-appb-I000052
The organic electroluminescent compound according to the present invention may be prepared as shown in following Schemes 1 and 2 but are not limited thereto.
[Scheme 1]
Figure PCTKR2011002489-appb-I000053
[Scheme 2]
Figure PCTKR2011002489-appb-I000054
wherein
R1 through R10, L1, L2, R11 and R12 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) represented by Chemical Formula 1.
In the organic electroluminescent device of the present invention, the organic layer may include the electroluminescent layer, and the electroluminescent layer may further include one or more host(s) besides one or more organic electroluminescent compounds of Chemical Formula 1 as an electroluminescent dopant. The host applied to the organic electroluminescent device of the present invention is not specifically limited but may be selected from following Chemical Formula 4 or 5.
[Chemical Formula 4]
(Ar101)a-L101-(Ar102)b
[Chemical Formula 5]
(Ar103)c-L102-(Ar104)d
wherein
L101 represents (C6-C30)arylene or (C4-C30)heteroarylene;
L102 represents anthracenylene;
Ar101 through Ar104 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 Ar101 through Ar104 is 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 (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, (C3-C30)cycloalkyl, halogen, cyano, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl, (C1-C30)alkyl with or without halogen substituent(s), (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 4 or 5 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.
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 the group consisting of arylamine compounds and styrylarylamine compounds, at the same time. The arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, 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 the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s). 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 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 of Chemical Formula 1, 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.
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 metal 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. 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 the 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 2
Figure PCTKR2011002489-appb-I000055
Preparation of Compound F
Compound D (10g, 16.99mmol) was dissolved in THF (100ml) and n-BuLi (50.99ml, 20.39mmol, 2.5M in hex) was slowly added thereto at -78℃. After stirring the mixture for 1 hour, DMF (3.2ml, 54.39mmol) was added thereto. After slowly raising temperature, the mixture was stirred at room temperature for 12 hours. Distilled water was added to the mixture and the mixture was extracted with MC. After drying with magnesium sulfate and distillation under reduced pressure, Compound F (4.7, 9.65mmol, 56.85%) was obtained by column separation.
Preparation of Compound H
Compound G (26g, 95.12mmol) and NaBH4 (5.39g, 142.68mmol) were mixed with THF (300ml). Methanol was slowly added to the mixture at 0℃. 2 hours later, the mixture was extracted with EA and washed with distilled water. After drying with magnesium sulfate, Compound H (26g, 94.42mmol, 99.27%) was obtained by column separation.
Preparation of Compound I
Compound H (26g, 94.42mmol) was dissolved in triethylphosphite (100ml) and iodine (23.96g, 94.42mmol) was dissolved in triethylphosphite (50ml). The two solutions were slowly mixed, and stirred at 100℃. 12 hours later, the mixture was cooled to room temperature and distilled under reduced pressure. The mixture was extracted with MC and washed with distilled water. After drying with magnesium sulfate and distillation under reduced pressure, Compound I (32g, 80.92mmol, 86.09%) was obtained by column separation.
Preparation of Compound 2
Compound F (4.7g, 9.65mmol) and Compound I (7.63g, (19.3mmol) were dissolved in THF (50ml) and potassium tert-butoxide (24ml, 24.12mmol, 1.0M in THF) was added to the mixture at 0℃. 2 hours later, distilled water was added and the mixture was extracted with MC. After drying with magnesium sulfate and distillation under reduced pressure, Compound 2 (4.3g, 4.43mmol, 45.97%) was obtained by column separation.
[Preparation Example 2] Preparation of Compound 101
Figure PCTKR2011002489-appb-I000056
Preparation of Compound L
After diphenylamine (20g, 118.2mmol), Compound k (24.04g, 130.02mmol), Pd(OAc)2 (1.3g, 5.91mmol), cesium carbonate (96.2g, 295.50mmol) and toluene (500ml) were mixed and tri-t-butylphophine (5.8ml, 11.82mmol, in 50% xylene) was stirred at 120℃. 10 hours later, the mixture was cooled to room temperature. Distilled water was added to the mixture and the mixture was extracted with EA. After drying with magnesium sulfate and distillation under reduced pressure, Compound L (14.7g, 53.58mmol, 45.41%) was obtained by column separation.
Preparation of Compound 101
Compound 101 (3g, 32%) was obtained using Compound L as an intermediate in the same manner as that of Preparation Example 1.
[Preparation Example 3] Preparation of Compound 106
Figure PCTKR2011002489-appb-I000057
Preparation of Compound M
After 4-bromotoluen (6.8ml, 55.2mmol) was added to a round bottom flask and vacuum dried, it was filled with nitrogen gas. The compound was dissolved by adding THF (200ml) to the round bottom flask and cooled to -78℃. After n-butyl lithium (22ml, 55.2mmol) was slowly added to the round bottom flask, the mixture was stirred for 1 hour while maintaining low temperature. 1 hour later, phenanthrenequinone (5g, 24mmol) was added at -78℃, and the mixture was stirred for 3 hours while heating to room temperature. Upon completion of the reaction, the mixture was extracted with ethyl ether and dried by removing remaining moisture with magnesium sulfate. Compound M (5.9g, 14.8mmol, 63%) was obtained by performing column separation on the obtained material.
Preparation of Compound N
Compound M (5g, 12.6mmol) was dissolved in AcOH (100ml) in a round bottom flask and stirred under reflux. Zn powder (4g, 63mmol) was added to the mixture. A solution that HCl (2.5ml) was dissolved in AcOH (12ml) was added to the round bottom flask. 30 minutes later, a solution that HCl (2.5m) was dissolved in Zn powder (4g, 63mmol) and AcOH (12ml) was added to the mixture. The mixture was stirred until there is no more reaction in thin layer chromatography (TLC). The mixture was extracted with MC, distilled water, sodium bicarbonate solution and NaCl solution and dried by removing remaining moisture with magnesium sulfate. Compound N (4.3g, 11.9mmol, 97%) was obtained by performing column separation on the obtained material.
Preparation of Compound O
After Compound N (5.8g, 16.1mmol), NBS (6.6g, (37mmol) and benzoyl peroxide (391mg, 1.61mmol) were added to a round bottom flask and vacuum dried, it was filled with nitrogen gas. After the compound was dissolved by adding CCl4 (193ml) to the round bottom flask, the mixture was stirred under reflux for 4 hours. Upon completion of the reaction, the mixture was extracted with MC and dried by removing remaining moisture with magnesium sulfate to go on to the next reaction.
Preparation of Compound P
After Compound O (11g, 21.3mmol) was added to a round bottom flask and vacuum dried, it was filled with nitrogen gas. After the compound was dissolved by adding triethylphosphite (40ml) to the round bottom flask, the mixture was stirred under reflux for 7 hours. Upon completion of the reaction, triethylphosphite was removed by a distillation device. Compound P (12.2g, 19.3mmol, 91%) was obtained by column separation.
Preparation of Compound 106
After Compound P (3g, 4.75mmol) and 4-(diphenylamino)benzaldehyde (3.1g, 11.4mmol) was added to a round bottom flask and vacuum dried, it was filled with nitrogen gas. After the compound was dissolved by adding THF (200ml) to the round bottom flask and cooled to 0℃, potassium-tert-butoxide (57ml, 57mmol) was slowly added and stirred for 10 minutes. After heated to room temperature, the mixture was stirred for 1 hour. Upon completion of the reaction, the mixture was extracted with EA and dried by removing remaining moisture with magnesium sulfate. Compound 106 (2g, 2.3mmol, 50%) was obtained by performing column separation on the obtained material.
Organic electroluminescent compounds 1 to 111 were prepared according to the procedure of Preparation Examples 1 and 3. 1H NMR and MS/FAB data of thus prepared organic electroluminescent compounds are given in Table 1.
Table 1
Comp. 1H NMR(CDCl3, 200 MHz) MS/FAB
found calculated
1 δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 869.10 868.38
2 δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.58~7.59(6H, m), 7.73~7.77(6H, m), 7.92(2H, m), 7.98~8(6H, m), 8.12(2H, m), 9.09(2H, m) 969.22 968.41
3 δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.55(4H, m), 7.61(2H, m), 7.77(4H, m), 7.98~8.12(8H, m), 8.42(2H, m), 8.55(2H, m), 9.09(2H, m) 969.22 968.41
4 δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2~7.25(16H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1021.29 1020.44
5 δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2~7.25(16H, m), 7.58~7.59(6H, m), 7.73~7.77(6H, m), 7.92(2H, m), 7.98~8(6H, m), 8.12(2H, m), 9.09(2H, m) 1121.41 1120.48
6 δ= 2.34(6H, s), 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.29~7.33(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 897.15 896.41
7 δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.3(4H, m), 7.39(4H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 905.08 904.36
8 δ= 3.83(6H, s), 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.05(4H, m), 7.2(8H, m), 7.68(4H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 929.15 928.40
9 δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.77(4H, m), 7.98~7.99(6H, m), 8.12(2H, m), 8.75(4H, m), 9.09(2H, m) 871.08 870.37
10 δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.17~7.2(10H, m), 7.4(2H, m), 7.69(2H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 881.16 880.29
11 δ= 6.63(8H, m), 6.81(4H, m), 6.95~6.98(6H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.54(12H, m), 7.73(2H, m), 7.87(2H, m), 7.98(2H, m), 8.07~8.12(4H, m), 9.09(2H, m) 969.22 968.41
12 δ= 6.63(8H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.49~7.57(14H, m), 7.74(2H, m), 7.83~7.84(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 969.22 968.41
13 δ= 6.63(8H, m), 6.69(4H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.56(16H, m), 7.64(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1021.29 1020.44
14 δ= 0.9(12H, m), 1.91(8H, m), 6.58~6.63(10H, m), 6.75~6.81(6H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.54(10H, m), 7.62(2H, m), 7.71(2H, m), 7.87(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1157.53 1156.57
15 δ= 1.51(8H, m), 2.09(8H, m), 6.58~6.63(10H, m), 6.75~6.81(6H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.54(10H, m), 7.62(2H, m), 7.71(2H, m), 7.87(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1153.49 1152.54
16 δ= 1.48(12H, m), 2.02(8H, m), 6.58~6.63(10H, m), 6.75~6.81(6H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.54(10H, m), 7.62(2H, m), 7.71(2H, m), 7.87(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1181.55 1180.57
17 δ= 3.49(8H, s), 6.58~6.63(10H, m), 6.75~6.81(6H, m), 6.95(4H, m), 7.2(16H, m), 7.41(2H, m), 7.51~7.54(10H, m), 7.62(2H, m), 7.71(2H, m), 7.87(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1249.58 1248.54
18 δ= 6.63(8H, m), 6.75~6.81(8H, m), 6.95(4H, m), 7.08(2H, m), 7.2(8H, m), 7.38~7.52(18H, m), 7.58(4H, m), 7.94~7.98(4H, m), 8.12(2H, m), 8.59(2H, m), 9.09(2H, m) 1199.48 1198.50
19 δ= 0.66(12H, s), 6.63(8H, m), 6.69(2H, m), 6.81(4H, m), 6.95~6.99(6H, m), 7.2(8H, m), 7.27(2H, m), 7.41(2H, m), 7.51~7.56(12H, m), 7.98(2H, m), 8.12~8.17(4H, m), 9.09(2H, m) 1133.57 1132.46
20 δ= 6.63(8H, m), 6.79~6.81(8H, m), 6.95(4H, m), 7.2(8H, m), 7.37~7.55(30H, m), 7.64~7.66(4H, m), 7.76(2H, m), 7.89(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1381.85 1380.52
21 δ= 1.3(8H, m), 1.45(8H, m), 6.63(8H, m), 6.79~6.81(8H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.64~7.66(4H, m), 7.76(2H, m), 7.89(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1185.64 1184.49
22 δ= 6.63(8H, m), 6.81(4H, m), 6.95(4H, m), 7.08(2H, m), 7.2(8H, m), 7.32(2H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.71(4H, m), 7.98~8.04(4H, m), 8.12(2H, m), 8.28(2H, m), 8.68(2H, m), 8.93(2H, m), 9.09(2H, m) 1069.34 1068.44
23 δ= 6.63(8H, m), 6.81(4H, m), 6.91~6.95(6H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.82~7.88(4H, m), 7.98(4H, m), 8.12(6H, m), 8.93(2H, m), 9.09(4H, m) 1069.34 1068.44
24 δ= 6.63(8H, m), 6.81(4H, m), 6.96(2H, m), 7.2(10H, m), 7.41~7.56(14H, m), 7.69(2H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) 871.08 870.37
25 δ= 6.63(8H, m), 6.7(2H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.41~7.52(12H, m), 7.86~7.88(4H, m), 8.07(2H, m), 8.97(2H, m) 871.08 870.37
26 δ= 6.63(8H, m), 6.81(4H, m), 6.95~6.99(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.36(2H, s), 8.61(2H, s), 8.97(2H, m) 873.05 872.36
27 δ= 6.63(8H, m), 6.81(4H, m), 6.95~6.99(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.33(2H, s), 8.97(2H, m) 875.03 874.35
28 δ= 6.63(8H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.41~7.43(4H, m), 7.51~7.56(10H, m), 7.98(2H, m), 8.12(2H, m), 8.32(2H, m), 8.68(2H, m), 8.82(2H, m), 9.09(2H, m) 971.19 970.40
29 δ= 6.63(8H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.33(2H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86~7.9(4H, m), 8.07(2H, m), 8.38(2H, m), 8.71(2H, m), 8.88(2H, m), 8.97(2H, m) 971.19 970.40
30 δ= 6.63(8H, m), 6.81(4H, m), 6.95(4H, m), 7.12(2H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.72(2H, m), 7.83~7.86(4H, m), 8.07(2H, m), 8.25(2H, m), 8.5(2H, m), 8.97(4H, m) 1073.29 1072.43
31 δ= 6.63(8H, m), 6.8~6.81(6H, m), 7.2(10H, m), 7.28(2H, m), 7.41(2H, m), 7.51~7.58(12H, m), 7.86(2H, m), 8.01(2H, m), 8.07(2H, m), 8.38(2H, m), 8.83(2H, m), 8.97(2H, m) 1073.29 1072.43
32 δ= 6.3(2H, m), 6.63(8H, m), 6.81(4H, m), 6.9~6.99(6H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) 881.16 880.29
33 δ= 6.54(2H, m), 6.63(8H, m), 6.81(4H, m), 6.95~7(6H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) 849.02 848.34
34 δ= 6.29(8H, m), 6.59(2H, s), 6.81~6.85(8H, m), 7.14(2H, s), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) 974.95 976.18
35 δ= 6.63(8H, m), 6.81(4H, m), 6.95~6.99(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) 885.11 884.28
36 δ= 6.63(8H, m), 6.81(4H, m), 6.95~6.99(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) 852.98 852.32
37 δ= 5.67(2H, m), 6.29(8H, m), 6.79~6.81(6H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.86(2H, m), 8.07(2H, m), 8.97(2H, m) 978.90 980.16
38 δ= 6.63(8H, m), 6.81(4H, m), 6.88(2H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.59(2H, m), 7.98(2H, m), 8.12(2H, m), 8.74(4H, m), 9.09(2H, m) 973.17 972.39
39 δ= 1.72(12H, s), 3.2(6H, s), 5.66(2H, m), 5.87(2H, m), 6.45(2H, m), 6.63(8H, m), 6.81~6.83(6H, m), 6.95(4H, m), 7.07~7.08(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1159.50 1158.56
40 δ= 3.2(6H, s), 5.7(2H, m), 5.91(2H, m), 6.49(2H, m), 6.63~6.67(10H, m), 6.81(4H, m), 6.92~6.95(6H, m), 7.13(2H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1107.34 1106.46
41 δ= 3.2(6H, s), 5.74(2H, m), 5.95(2H, m), 6.53(2H, m), 6.63(8H, m), 6.81~6.82(6H, m), 6.95~6.97(6H, m), 7.2~7.22(10H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1233.26 1234.30
42 δ= 3.2(6H, s), 5.88(2H, m), 6.47(2H, m), 6.63(8H, m), 6.81~6.84(6H, m), 6.91~6.95(8H, m), 7.16~7.2(10H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1139.47 1138.41
43 δ= 2.88(8H, m), 3.2(6H, s), 5.69(2H, m), 5.9(2H, m), 6.48(2H, m), 6.63(8H, m), 6.81~6.82(6H, m), 6.95(4H, m), 7.07~7.1(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1131.45 1130.53
44 δ= 3.2(6H, s), 5.74(2H, m), 5.95(2H, m), 6.53(2H, m), 6.63(8H, m), 6.81~6.82(6H, m), 6.95~7.03(10H, m), 7.2(8H, m), 7.28(2H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1127.42 1126.50
45 δ= 3.2(6H, s), 5.8(2H, m), 6.01(2H, m), 6.59~6.63(10H, m), 6.81(4H, m), 6.88(2H, m), 6.95(4H, m), 7.2(8H, m), 7.32(2H, m), 7.41~7.57(16H, m), 7.85(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1227.54 1226.53
46 δ= 1.16(8H, m), 1.48(4H, m), 1.58(8H, m), 2.57(2H, m), 6.6(4H, m), 6.77(2H, m), 6.95(4H, m), 7.23(4H, m), 7.33(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.8(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 881.20 880.48
47 δ= 1.16(16H, m), 1.48(8H, m), 1.58(16H, m), 2.57(4H, m), 6.76(4H, m), 6.95(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.84(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 893.29 892.57
48 δ= 1.76(40H, m), 1.87(8H, m), 2.1(8H, m), 2.89(4H, m), 6.76(4H, m), 6.95(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.84(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1101.59 1100.69
49 δ= 6.63(4H, m), 6.95(4H, m), 7.36~7.41(6H, m), 7.49~7.52(16H, m), 7.74~7.77(12H, m), 7.84~7.88(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1069.34 1068.44
50 δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.2(4H, m), 7.36~7.41(4H, m), 7.49~7.52(12H, m), 7.74~7.77(8H, m), 7.84~7.88(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 969.22 968.41
51 δ= 6.63(4H, m), 6.95~6.98(8H, m), 7.38~7.41(6H, m), 7.51~7.57(20H, m), 7.77(4H, m), 7.98~8.12(12H, m), 9.09(2H, m) 1069.34 1068.44
52 δ= 6.63(8H, m), 6.81(2H, m), 6.95~6.98(6H, m), 7.2(4H, m), 7.38~7.41(4H, m), 7.51~7.57(14H, m), 7.77(4H, m), 7.98~8.12(8H, m), 9.09(2H, m) 969.22 968.41
53 δ= 6.63(4H, m), 6.69(8H, m), 6.95(4H, m), 7.41(6H, m), 7.51~7.54(32H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1173.48 1172.51
54 δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.2(4H, m), 7.38~7.41(10H, m), 7.51~7.52(8H, m), 7.77~7.8(6H, m), 7.88~7.9(8H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1069.34 1068.44
55 δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.08(2H, m), 7.2(4H, m), 7.32(2H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.71~7.88(12H, m), 7.98(2H, m), 8.12(4H, m), 8.68(2H, m), 8.93(2H, m), 9.09(2H, m) 1069.34 1068.44
56 δ= 6.63(4H, m), 6.95(4H, m), 7.08(4H, m), 7.32(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.71~7.88(20H, m), 7.98(2H, m), 8.12(6H, m), 8.68(4H, m), 8.93(4H, m), 9.09(2H, m) 1269.57 1268.51
57 δ= 6.63(8H, m), 6.81(2H, m), 6.91~6.95(6H, m), 7.2(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77~7.88(12H, m), 7.98(2H, m), 8.12(6H, m), 8.93(4H, m), 9.09(2H, m) 1069.34 1068.44
58 δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.02(2H, m), 7.2(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.71~7.88(14H, m), 7.98(2H, m), 8.12~8.13(6H, m), 8.93(2H, m), 9.09(2H, m) 1069.34 1068.44
59 δ= 6.63(8H, m), 6.81(2H, m), 6.91~6.95(6H, m), 7.2(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.71~7.88(16H, m), 7.98(2H, m), 8.12(6H, m), 9.09(2H, m) 1117.38 1116.44
60 δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.71~7.82(14H, m), 7.98~8(6H, m), 8.12(2H, m), 9.09(2H, m) 1117.38 1116.44
61 δ= 6.63(4H, m), 6.95(4H, m), 7.02(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77~7.88(24H, m), 7.98(2H, m), 8.12~8.13(14H, m), 8.93(8H, m), 9.09(2H, m) 1469.80 1468.57
62 δ= 6.63(8H, m), 6.81(4H, m), 6.95(4H, m), 7.2(4H, m), 7.41(2H, m), 7.51~7.57(10H, m), 7.73~7.78(8H, m), 7.88(2H, m), 7.98(2H, m), 8.1~8.12(6H, m), 8.42(4H, m), 9.09(2H, m) 1117.38 1116.44
63 δ= 6.63(4H, m), 6.95(4H, m), 7.12(2H, m), 7.41(2H, m), 7.51~7.58(16H, m), 7.72~7.77(6H, m), 7.83(2H, m), 7.94~7.98(4H, m), 8.12(2H, m), 8.22~8.25(4H, m), 8.38(4H, m), 8.83(4H, m), 9.09(2H, m) 1277.47 1276.47
64 δ= 0.9(24H, m), 1.91(16H, m), 6.58~6.63(8H, m), 6.75(4H, m), 6.95(4H, m), 7.28(4H, m), 7.38~7.41(6H, m), 7.51~7.55(12H, m), 7.62(4H, m), 7.77(4H, m), 7.87(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1445.95 1444.76
65 δ= 0.9(12H, m), 1.91(8H, m), 6.58~6.63(10H, m), 6.75~6.81(4H, m), 6.95(4H, m), 7.2(4H, m), 7.28(2H, m), 7.38~7.41(4H, m), 7.51~7.55(10H, m), 7.62(2H, m), 7.77(4H, m), 7.87(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1157.53 1156.57
66 δ= 0.9(12H, m), 1.91(8H, m), 6.47(2H, s), 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.2~7.24(6H, m), 7.41~7.52(16H, m), 7.61(2H, m), 7.77(4H, m), 7.98(2H, m), 8.08~8.12(6H, m), 8.46(2H, m), 9.09(2H, m) 1257.64 1256.60
67 δ= 0.9(24H, m), 1.91~1.93(16H, m), 6.63(4H, m), 6.77(3H, m), 6.95(4H, m), 7.18(3H, m), 7.24~7.29(5H, m), 7.41~7.52(15H, m), 7.61(4H, m), 7.71~7.77(11H, m), 7.85(1H, m), 7.98~8.02(5H, m), 8.09~8.16(7H, m), 9.09(2H, m) 1646.19 1644.82
68 δ= 6.58~6.63(10H, m), 6.75~6.81(4H, m), 6.95(4H, m), 7.11(8H, m), 7.2~7.41(22H, m), 7.51~7.55(10H, m), 7.62(2H, m), 7.77(4H, m), 7.87(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1349.70 1348.57
69 δ= 6.39(2H, m), 6.55(2H, m), 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.16~7.2(8H, m), 7.28(4H, m), 7.35~7.41(8H, m), 7.5~7.55(14H, m), 7.75~7.77(6H, m), 7.87(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1345.67 1344.54
70 δ= 5.19(4H, s), 6.39(2H, m), 6.51(2H, m), 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.03~7.06(10H, m), 7.15~7.2(12H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1221.53 1220.51
71 δ= 5.19(4H, s), 6.39(2H, m), 6.51(2H, m), 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.03~7.06(10H, m), 7.15~7.2(12H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1221.53 1220.51
72 δ= 6.62~6.63(8H, m), 6.7(4H, m), 6.95(4H, m), 7.41(2H, m), 7.51~7.55(12H, m), 7.77(4H, m), 7.98(2H, m), 8.07~8.12(6H, m), 9.09(2H, m) 873.05 872.36
73 δ= 6.62~6.63(6H, m), 6.95(4H, m), 7.19(2H, m), 7.37~7.41(8H, m), 7.51~7.57(10H, m), 7.69~7.8(10H, m), 7.94~7.98(4H, m), 8.12(2H, m), 8.22(2H, m), 8.75(2H, m), 9.09(2H, m) 1073.29 1072.43
74 δ= 6.95(4H, m), 7.25~7.33(6H, m), 7.41(2H, m), 7.5~7.52(14H, m), 7.62~7.63(6H, m), 7.94~7.98(4H, m), 8.12(4H, m), 8.55(2H, m), 9.09(2H, m) 865.07 864.35
75 δ= 1.72(12H, s), 6.55(4H, m), 6.63(4H, m), 6.73(4H, m), 6.95(4H, m), 7.02~7.05(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 949.23 948.44
76 δ= 6.38(8H, m), 6.56(8H, m), 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.2(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1047.29 1046.43
77 δ= 6.63(4H, m), 6.95~6.97(8H, m), 7.16~7.21(12H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 929.20 928.29
78 δ= 6.59~6.63(8H, m), 6.77(4H, m), 6.89~6.95(12H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 897.07 896.34
79 δ= 6.63(4H, m), 6.73(8H, m), 6.95(4H, m), 7.21(4H, m), 7.3(4H, m), 7.37~7.55(30H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1229.66 1228.46
80 δ= 1.3(8H, m), 1.45(8H, m), 6.63(4H, m), 6.73(8H, m), 6.95(4H, m), 7.21(4H, m), 7.3(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1033.45 1032.43
81 δ= 2.71(8H, s), 6.63(4H, m), 6.73(8H, m), 6.95(4H, m), 7.11~7.14(8H, m), 7.21(4H, m), 7.3(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1129.54 1128.43
82 δ= 2.88(8H, m), 6.58~6.63(8H, m), 6.76(4H, m), 6.95(4H, m), 7.02~7.04(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 921.18 920.41
83 δ= 6.63(8H, m), 6.81(4H, m), 6.95~7.05(12H, m), 7.25(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 917.14 916.38
84 δ= 6.63(4H, m), 6.69(4H, m), 6.87(4H, m), 6.95(4H, m), 7.16(4H, m), 7.41~7.54(18H, m), 7.77(4H, m), 7.85(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1017.26 1016.41
85 δ= 1.53(12H, m), 3.63(4H, m), 5.99~6.05(8H, m), 6.95(4H, m), 7.22~7.33(16H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1077.40 1076.51
86 δ= 6.63(4H, m), 6.95(4H, m), 7.14(4H, m), 7.32~7.41(10H, m), 7.51~7.52(8H, m), 7.66(4H, m), 7.77(4H, m), 7.89(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1029.18 1028.36
87 δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.14(2H, m), 7.2(4H, m), 7.32~7.41(6H, m), 7.51~7.52(8H, m), 7.66(2H, m), 7.77(4H, m), 7.89(2H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 949.14 948.37
88 δ= 6.34(4H, m), 6.63(4H, m), 6.95(4H, m), 7.41(2H, m), 7.5~7.52(16H, m), 7.77~7.79(8H, m), 7.98(6H, m), 8.12(2H, m), 9.09(2H, m) 1093.45 1092.27
89 δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.2(4H, m), 7.41(2H, m), 7.51~7.53(12H, m), 7.77(4H, m), 7.98~8.01(4H, m), 8.12(2H, m), 8.18(2H, m), 9.09(2H, m) 983.25 982.32
90 δ= 6.63(4H, m), 6.95(4H, m), 7.39~7.41(10H, m), 7.51~7.52(8H, m), 7.74~7.77(12H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1033.14 1032.34
91 δ= 1.35(36H, s), 6.55(8H, m), 6.63(4H, m), 6.95~7.01(12H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1093.53 1092.63
92 δ= 0.25(36H, s), 6.61~6.63(12H, m), 6.95(4H, m), 7.15(8H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1157.83 1156.54
93 δ= 6.63(4H, m), 6.73(8H, m), 6.95(4H, m), 7.21(8H, m), 7.37~7.55(70H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1902.66 1900.73
94 δ= 6.61~6.63(12H, m), 6.95~6.99(12H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 941.06 940.34
95 δ= 6.56(8H, m), 6.63(4H, m), 6.95(4H, m), 7.37~7.41(10H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1141.09 1140.33
96 δ= 6.63(4H, m), 6.81(8H, m), 6.95(4H, m), 7.39~7.41(10H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 969.14 968.36
97 δ= 3.83(12H, s), 6.52(8H, m), 6.63(4H, m), 6.74(8H, m), 6.95(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 989.20 988.42
98 δ= 6.63(8H, m), 6.69(4H, m), 6.81(2H, m), 6.95(4H, m), 7.2(4H, m), 7.41(4H, m), 7.51~7.54(20H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 1021.29 1020.44
99 δ= 6.62~6.63(8H, m), 6.7(4H, m), 6.95(4H, m), 7.41(2H, m), 7.51~7.55(12H, m), 7.77(4H, m), 7.98(2H, m), 8.07~8.12(6H, m), 9.09(2H, m) 873.05 872.36
100 δ= 6.63(4H, m), 6.95(4H, m), 7.27(4H, m), 7.36~7.41(6H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98~8.12(12H, m), 9.09(2H, m) 873.05 872.36
101 δ= 6.63(8H, m), 6.7(2H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.46(2H, m), 7.58~7.59(6H, m), 7.73(2H, m), 7.86~7.92(6H, m), 8(4H, m), 8.07(2H, m), 8.97(2H, m) 971.19 970.40
102 δ= 6.63(8H, m), 6.81(2H, m), 6.95(4H, m), 7.2(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.77(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 879.16 878.44
103 δ= 3.05(4H, m), 4.14(4H, m), 6.55~6.6(6H, m), 6.72(2H, m), 6.95(4H, m), 7.05~7.07(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.8(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 768.98 768.35
104 δ= 1.25(6H, m), 1.81(4H, m), 2.79~2.8(6H, m), 6.55~6.6(6H, m), 6.72(2H, m), 6.95(4H, m), 7.05~7.07(4H, m), 7.41(2H, m), 7.51~7.52(8H, m), 7.8(4H, m), 7.98(2H, m), 8.12(2H, m), 9.09(2H, m) 825.09 824.41
105 δ= 6.52(2H, m), 6.87(2H, m), 6.95(4H, m), 7.33(2H, m), 7.41(2H, m), 7.5~7.52(12H, m), 7.6~7.62(6H, m), 7.93~7.98(6H, m), 8.12(2H, m), 9.09(2H, m) 764.95 764.32
106 δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.56(4H, m), 7.64(4H, m), 7.77~7.88(8H, m), 8.12(2H, m), 8.93(2H, m) 869.10 858.38
107 δ= 6.63(8H, m), 6.81(4H, m), 6.96(2H, m), 7.2(10H, m), 7.44~7.45(6H, m), 7.56~7.59(6H, m), 7.69(2H, m), 7.82~7.88(4H, m), 8.12(2H, m), 8.93(2H, m) 871.08 870.37
108 δ= 6.63(8H, m), 6.81(4H, m), 6.96(2H, m), 7.2(8H, m), 7.45~7.49(4H, m), 7.69(2H, m), 7.81~7.88(10H, m), 8.12(2H, m), 8.85(2H, m), 8.93(2H, m) 873.05 872.36
109 δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.56(12H, m), 7.64(4H, m), 7.77(4H, m), 8.1(2H, m), 8.34(2H, m), 8.99(2H, m) 1021.29 1020.44
110 δ= 6.63(12H, m), 6.81(4H, m), 6.95(4H, m), 7.2(8H, m), 7.41(2H, m), 7.51~7.56(12H, m), 7.64(4H, m), 7.77(4H, m), 8.04(2H, m), 8.18(2H, m), 9.15(2H, m) 1021.29 1020.44
111 δ= 6.62~6.63(8H, m), 6.7(4H, m), 6.95(4H, m), 7.55~7.56(8H, m), 7.64(4H, m), 7.77~7.88(8H, m), 8.07~8.12(6H, m), 8.93(2H, m) 873.05 872.36
[Examples 1-11] 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 formed thereon as follows. DNA (Examples 1 to 3) was placed in a cell of the vacuum vapor deposition apparatus as a host, and the compound according to the present invention was placed in another cell as a dopant. The two materials were vapor-deposited at a rate of 100:3 to form an electroluminescent layer having a thickness of 30 nm on the hole transport layer.
Figure PCTKR2011002489-appb-I000058
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.
Each compound used in the OLED had been purified by vacuum sublimation at 10-6torr.
Luminescence efficiency of the OLED devices containing the organic electroluminescent compound according to the present invention manufactured in Examples 1 to 3 was measured at 1,000 cd/m2. The result is given in Table 2.
Table 2
No. EL material 1 EL material 2 Luminescence efficiency (cd/A) Color
Example 1 DNA Compound 88 3.4 Deep blue
2 DNA Compound 94 3.9 Deep blue
3 DNA Compound 102 3.5 Deep blue
As seen from Table 2, the organic electroluminescent compounds of the present invention provide deep blue color. That, when a blue color having the level of about CIE y = 0.1 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 PCTKR2011002489-appb-I000059
    wherein
    R1, R4, R7 and R10 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl], RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl], RdY- [wherein Y represents O or S, and Rd represents (C1-C30)alkyl or (C6-C30)aryl] or
    Figure PCTKR2011002489-appb-I000060
    , except for the case where two of R1, R4, R7 and R10 are hydrogen;
    R2, R3, R5, R6, R8 and R9 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl], RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl] or RdY- [wherein Y represents O or S, and Rd represents (C1-C30)alkyl or (C6-C30)aryl];
    L1 represents a single bond, (C6-C30)arylene or (C2-C30)heteroarylene;
    L2 represents (C6-C30)arylene, (C2-C30)heteroarylene or
    Figure PCTKR2011002489-appb-I000061
    ;
    R11 and R12 independently represent (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl or
    Figure PCTKR2011002489-appb-I000062
    , or may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring, and the carbon atom of the alkylene may be substituted by NR21, O or S, wherein R21 represents hydrogen, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered heterocycloalkyl, (C3-C30)cycloalkyl, halogen, cyano, (C6-30)aryl, (C2-30)heteroaryl or RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl];
    Z1 and Z2 independently represent -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Se- or -Si(R34)(R35);
    R31 through R35 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl] or RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl], or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
    the alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R1 through R10 and R31 through R35; the arylene or heteroarylene of L1 and L2; the cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R11 and R12; and the fused ring formed by link between R11 and R12 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl;
    the heterocycloalkyl or heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P; and
    m represents an integer 0, 1 or 2.
  2. The organic electroluminescent compound according to claim 1, which is represented by Chemical Formula 2 or 3:
    [Chemical Formula 2]
    Figure PCTKR2011002489-appb-I000063
    [Chemical Formula 3]
    Figure PCTKR2011002489-appb-I000064
    wherein
    L11 and L12 independently represent (C6-C30)arylene, (C2-C30)heteroarylene or
    Figure PCTKR2011002489-appb-I000065
    ;
    L21 and L22 independently represent (C6-C30)arylene or (C2-C30)heteroarylene;
    R2, R3, R5, R6, R8 and R9 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl or (C2-30)heteroaryl;
    R41 through R44 independently represent (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl or
    Figure PCTKR2011002489-appb-I000066
    , or may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form a fused ring, and the carbon atom of the alkylene may be substituted by NR21, O or S, wherein R21 represents hydrogen, (C1-C30)alkyl, halo(C1-C30)alkyl, (C1-C30)alkoxy, morpholino, thiomorpholino, piperidino, 5- to 7-membered heterocycloalkyl, (C3-C30)cycloalkyl, halogen, cyano, (C6-30)aryl, (C2-30)heteroaryl or RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl];
    Z1 and Z2 independently represent -(CR31R32)m-, -(R31)C=C(R32)-, -N(R33)-, -S-, -O-, -Se- or -Si(R34)(R35);
    R31 through R35 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl] or RaRbRcSi- [Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl], or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
    R1, R4, R7 and R10 independently represent hydrogen, (C1-C30)alkyl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C6-30)aryl, (C2-30)heteroaryl, -NReRf [wherein Re and Rf independently represent (C1-C30)alkyl or (C6-C30)aryl], RaRbRcSi- [wherein Ra, Rb and Rc independently represent (C1-C30)alkyl or (C6-C30)aryl] or RdY- [wherein Y represents O or S, and Rd represents (C1-C30)alkyl or (C6-C30)aryl];
    the alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl of R1 through R10; and the arylene or heteroarylene of L11, L12, L21 and L22 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl; and
    m represents an integer 0, 1 or 2.
  3. The organic electroluminescent compound according to claim 2, wherein L11 and L12 independently represent phenylene, naphthalene, biphenylene, phenanthrylene, pyrazinylene, triazinylene, quinolylene, phenanthrolinylene, thienylene, furylene, selenophenylene, thiadiazolylene, oxadiazolylene, selenadiazolylene or quinoxalinylene, or a divalent group selected from the following structures:
    Figure PCTKR2011002489-appb-I000067
    R31 through R35 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, phenyl, naphthyl, biphenyl, fluorenyl or phenanthryl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
    L21 and L22 independently represent phenylene, naphthylene, anthracenylene, fluorenylene, phenanthrylene, biphenylene, triphenylene, fluoranthenylene, chrysenylene, pyrenylene, perylenylene, pyridinylene, furylene, thiophenylene, selenophenylene, pyrazinylene, pyridazinylene, quinolinylene or quinoxalinylene;
    R2, R3, R5, R6, R8 and R9 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, triazinyl or pyrimidyl;
    R41 through R44 independently represent cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, indenyl, fluorenyl, benzofluorenyl, spirobifluorenyl, anthracenyl, pyrenyl, phenanthryl, triphenylenyl, fluoranthenyl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, triazinyl, pyrimidyl or
    Figure PCTKR2011002489-appb-I000068
    ;
    R1, R4, R7 and R10 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, pyridyl, furyl, thiophenyl, quinolyl, isoquinolyl, phenanthrolinyl, carbazolyl, triazinyl or pyrimidyl; and
    L11, L12, L21, L22, R1 through R10 and R41 through R44 may be further substituted by one or more substituent(s) selected from deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C1-C30)alkoxy, cyano, (C1-C30)alkylsilyl, (C6-C30)arylsilyl, halo(C1-C30)alkyl, (C3-C30)heteroaryl, (C3-C30)cycloalkyl, nitro and hydroxyl.
  4. The organic electroluminescent compound according to claim 3, wherein
    Figure PCTKR2011002489-appb-I000069
    and
    Figure PCTKR2011002489-appb-I000070
    are independently selected from the following structures:
    Figure PCTKR2011002489-appb-I000071
    wherein
    R31 through R35 independently represent (C1-C30)alkyl or (C6-C30)aryl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring.
  5. An organic electroluminescent device comprising the organic electroluminescent compound according to any one 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) according to any of claims 1 to 4 and one or more host(s) selected from the compounds represented by Chemical Formula 4 or 5:
    [Chemical Formula 4]
    (Ar101)a-L101-(Ar102)b
    [Chemical Formula 5]
    (Ar103)c-L102-(Ar104)d
    wherein
    L101 represents (C6-C30)arylene or (C4-C30)heteroarylene;
    L102 represents anthracenylene;
    Ar101 through Ar104 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 Ar101 through Ar104 is 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 (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, (C3-C30)cycloalkyl, halogen, cyano, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl and tri(C6-C30)arylsilyl, (C1-C30)alkyl with or without halogen substituent(s), (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 amine compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds.
  8. The organic electroluminescent device according to claim 6, wherein the organic layer further comprises 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.
  9. The organic electroluminescent device according to claim 6, the organic layer comprises an electroluminescent layer and a charge generating layer.
  10. The organic electroluminescent device according to claim 6, which is a white light-emitting organic electroluminescent device, wherein the organic layer further comprises one or more organic electroluminescent layer(s) emitting blue, red or green light.
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