WO2011115378A1 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

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

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Publication number
WO2011115378A1
WO2011115378A1 PCT/KR2011/001435 KR2011001435W WO2011115378A1 WO 2011115378 A1 WO2011115378 A1 WO 2011115378A1 KR 2011001435 W KR2011001435 W KR 2011001435W WO 2011115378 A1 WO2011115378 A1 WO 2011115378A1
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Prior art keywords
substituent
organic electroluminescent
fused
aryl
alkyl
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PCT/KR2011/001435
Other languages
French (fr)
Inventor
Hee Choon Ahn
Mi Ran Seo
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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Priority to CN2011800243671A priority Critical patent/CN102933530A/en
Priority to JP2012558067A priority patent/JP5797672B2/en
Publication of WO2011115378A1 publication Critical patent/WO2011115378A1/en

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    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom

Definitions

  • the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same, more particularly, to novel organic electroluminescent compounds used as an electroluminescent material and an organic electroluminescent device using the same.
  • 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].
  • An organic EL device is a device wherein, when charge is applied to an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole form a pair and then become extinct with emitting light.
  • a device can be formed on a transparent flexible substrate such as plastics. The device can be operated at a lower voltage (not more than 10 V) with relatively lower power consumption but excellent color purity, as compared to a plasma display panel or an inorganic EL display. Since the organic electroluminescent (EL) devices can develop three colors (green, blue and red), they have been focused as full colored display devices for next generation.
  • 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 organic EL device commonly has a configuration of anode/hole injection layer (HIL)/hole transport layer (HTL)/emission material layer (EML)/electron transport layer (ETL)/electron injection layer (EIL)/cathode.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML emission material layer
  • ETL electron transport layer
  • EIL electron injection layer
  • the electroluminescent materials may be divided into host materials and dopant materials.
  • an electroluminescent layer prepared by doping a dopant in a host is known to provide superior EL property.
  • development of an organic EL device having high efficiency and long operation life is becoming an imminent task.
  • development of materials which are much superior to existing electroluminescent materials is urgently needed.
  • 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 conventional materials do not form a thin film layer of host-dopant but is formed of a single layer. Also, it is determined that they have a difficulty in commercialization in view of color purity and efficiency. There is also a problem in that reliable data on long lifespan are not sufficient.
  • green fluorescent materials a system for doping coumarin derivatives (Compound d, C545T), quinacridone derivatives (Compound e), DPT(Compound f) as a dopant with Alq as a host at several to several tens of % has been developed and widely used.
  • These conventional electroluminescent materials show a performance of a level that they can be commercialized in an initial luminous efficiency.
  • the initial luminous efficiency rapidly decreases and there is a problem in the operation life. Accordingly, the green fluorescent material has a limitation that it is difficult to be adopted in a high-performance panel of a large screen.
  • the green fluorescent material does not allow an enough operation life to the OLED device, it is required to develop more stable host materials having superior performance.
  • an object of the present invention is to provide an organic electroluminescent compound having luminescence efficiency and device operation life improved over existing materials and having superior backbone with appropriate color coordinates in order to solve the aforesaid problems.
  • Another object of the present invention is to provide an organic electroluminescent device employing the organic electroluminescent compound as an electroluminescent material.
  • the present invention provides an organic electroluminescent compound represented by Chemical Formula 1 and an organic electroluminescent device using the same.
  • the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life and consuming less power due to improved power efficiency.
  • R 1 through R 2 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s)or 5- to 7-membered heterocycloalkyl with or without substituent(s);
  • R 12 through R 19 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, nitro, hydroxyl, -NR 21 R 22 , -BR 23 R 24 , -PR 25 R
  • Ar independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, nitro, hydroxyl, -NR 21 R 22 , -BR 23 R 24 , -PR 25 R 26 ,
  • A represents a chemical bond, (C6-C30)arylene with or without substituent(s), (C2-C30)heteroarylene with or without substituent(s) or (C6-C30)arylenethio with or without substituent(s);
  • B represents a chemical bond, (C2-C30)alkylene with or without substituent(s), (C6-C30)arylene with or without substituent(s), (C3-C30)heteroarylene with or without substituent(s), 5- to 7-membered heterocycloalkylene with or without substituent(s), 5- to 7-membered heterocycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkylene with or without substituent(s), (C3-C30)cycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C6-C30)arylene fused with one or more alicyclic ring(s) with or without substituent(s), (C2-C30)alkenylene with or without substituent(s), (C2-C30)alkynylene with or without substituent(s), (C6-C30)ar(C1-C30)alkylene
  • R 21 through R 32 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)heterocycloalkyl with or without substituent(s), or each of them may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
  • Y represents S or O
  • a and b independently represent an integer from 1 to 3;
  • each A may be identical or different when a is 2 or greater, and each B may be identical or different when b is 2 or greater, and adjacent substituents may be linked to each other to form a ring;
  • alkyl in the present invention, “alkyl”, “alkoxy” and other substituents containing “alkyl” moiety include both linear and branched species.
  • the cycloalkyl includes polycyclic hydrocarbon ring such as adamantyl with or without substituent(s) or (C7-C30)bicycloalkyl with or without substituent(s) as well as a monocyclic hydrocarbon 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 aryls linked by single bond(s).
  • 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
  • the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • the heteroaryl also includes heteroaryl groups having single bond 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
  • the '(C1-C30)alkyl' groups described herein may include (C1-C20)alkyl or (C1-C10)alkyl and the '(C6-C30)aryl' groups include (C6-C20)aryl or (C6-C12)aryl.
  • the '(C3-C30)heteroaryl' groups include (C3-C20)heteroaryl or (C3-C12)heteroaryl and the '(C3-C30)cycloalkyl' groups include (C3-C20)cycloalkyl or (C3-C7)cycloalkyl.
  • the '(C2-C30)alkenyl or alkynyl' group include (C2-C20)alkenyl or alkynyl, (C2-C10)alkenyl or alkynyl.
  • R 1 through R 2 , R 3 through R 11 , R 12 through R 19 , Ar, A, B and R 21 through R 32 may be further substituted by one or more substituent(s) selected from the group consisting of deuterium, halogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), R a R b R c Si-, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, -NR d R e ,
  • the A represents a chemical bond, (C6-C30)arylene with or without substituent(s), (C2-C30)heteroarylene with or without substituent(s) or (C6-C30)arylenethio with or without substituent(s);
  • B represents a chemical bond, (C6-C30)arylene with or without substituent(s), (C3-C30)heteroarylene with or without substituent(s), 5- to 7-membered heterocycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C6-C30)arylene fused with one or more alicyclic ring(s) with or without substituent(s), (C2-C30)alkenylene with or without substituent(s) or (C2-C30)alkynylene with or without substituent(s); and R 1 through R 19 independently represent hydrogen
  • the Ar represents hydrogen, deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, fluoro, trimethylsilyl, triethylsilyl, tripropylsilyl, tri(t-butyl)silyl, t-butyldimethylsilyl, dimethylphenylsilyl, triphenylsilyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, t
  • the A is selected from a chemical bond or the following structures:
  • the organic electroluminescent compound is selected from the following compounds but the present invention is not limited by the compounds.
  • the organic electroluminescent compound according to the present invention may be prepared as shown in following Scheme 1.
  • R 1 through R 2 , R 3 through R 11 , R 12 through R 19 , A, B, Ar, a and b are the same as definition in the 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 comprises an electroluminescent layer, in which the organic electroluminescent compounds of Chemical Formula 1 is used as a host or dopant material.
  • the organic electroluminescent compounds of Chemical Formula 1 When the organic electroluminescent compounds of Chemical Formula 1 are used as the host, one or more dopant is included.
  • the dopant 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 2:
  • Ar 101 and Ar 102 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s), (C6-C30)arylamino with or without substituent(s), (C1-C30)alkylamino, 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), or each of Ar 101 and Ar 102 may be linked via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic
  • Ar 103 represents (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s) or a substituent selected from the following structures, when c is 1;
  • Ar 103 represents (C6-C30)arylene with or without substituent(s), (C4-C30)heteroarylene with or without substituent(s) or a substituent selected from the following structures, when c is 2;
  • Ar 104 and Ar 105 independently represent (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);
  • R 111 through R 122 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)heterocycloalkyl with or without substituent(s), or each of R 111 through R 122 may be linked to an adjacent substituent to form a (C3-C30)aliphatic ring with or without substituent(s), a (C5-C30)heteroaliphatic ring with or without substituent(s), a (C6-C30)aromatic ring with or without substituent(s) or a (C6-C30)heteroaromatic ring with or without substituent(s);
  • Y represents S or O
  • d represents an integer from 1 to 4.
  • e represents an integer 0 or 1.
  • the dopant compounds of Chemical Formula 2 may be exemplified as Compounds having following structures but are not limited thereto:
  • the organic electroluminescent compounds of Chemical Formula 1 are used as the dopant in the electroluminescent layer, one or more host is included.
  • 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 Formulas 3 to 4:
  • L 11 represents (C6-C60)arylene with or without substituent(s) or (C4-C60)heteroarylene with or without substituent(s);
  • L 12 represents anthracenylene with or without substituent(s);
  • R 201 through R 212 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s)or (C3-C30)heteroaryl with or without substituent(s);
  • X represents S or O
  • f, g, h and i independently represent an integer of 0 to 4.
  • the host compounds of Chemical Formulas 3 to 4 may be exemplified as Compounds having following structures 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.
  • 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.
  • the compound emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application No. 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 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 and excellent life property, it may be used to manufacture OLED devices having very superior operation life.
  • Target Compound 57 (37g, 79%) was obtained by purification via column chromatography using dichloromethane and hexane as an eluent.
  • Organic electroluminescent compounds 1 to 73 were prepared according to the procedure of Preparation Examples 1 and 2. 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.
  • Compound 1 was placed in a cell of a vacuum vapor deposition apparatus as a host, and Compound D was placed in another cell as a dopant.
  • the two materials were evaporated at different rates such that an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer through doping at 2 to 5 wt%.
  • Each compound used in the OLED was purified by vacuum sublimation at 10 -6 torr.
  • An OLED device was manufactured as in Example 1 except that Compound 4 was added as a host material on the electroluminescent layer.
  • An OLED device was manufactured as in Example 1 except that Compound 5 was added as a host material on the electroluminescent layer.
  • An OLED device was manufactured as in Example 1 except that Compound 14 was added as a host material on the electroluminescent layer.
  • An OLED device was manufactured as in Example 1 except that Compound 58 was added as a host material on the electroluminescent layer.
  • An OLED device was manufactured as in Example 1 except that Compound 59 was added as a host material on the electroluminescent layer and N 9 ,N 9 ,N 10 ,N 10 , 2,6-hexaphenylanthracene-9,10-diamine(Compound E) was used as an electroluminescent dopant.
  • An OLED device was manufactured as in Example 6 except that Compound 53 was added as a host material on the electroluminescent layer.
  • An OLED device was manufactured as in Example 6 except that Compound 45 was added as a host material on the electroluminescent layer.
  • An OLED device was manufactured as in Example 6 except that Compound 62 was added as a host material on the electroluminescent layer.
  • An OLED device was manufactured as in Example 1 except that dinaphthyl anthracene (DNA) was added as a host material on the electroluminescent layer and Compound 69 was used as a dopant.
  • DNA dinaphthyl anthracene
  • An OLED device was manufactured as in Example 1 except that dinaphthyl anthracene (DNA) was added as a host material on the electroluminescent layer and Compound 68 was used as a dopant.
  • DNA dinaphthyl anthracene
  • An OLED device was manufactured as in Example 1 except that dinaphthyl anthracene (DNA) was added as a host material on the electroluminescent layer and Compound 73 was used as a dopant.
  • DNA dinaphthyl anthracene
  • An OLED was manufactured in the same manner as Example 1 except that dinaphthyl anthracene (DNA) instead of the compounds of the present invention as a host material at one cell of the vacuum vapor deposition apparatus and Compound D as a dopant were used.
  • DNA dinaphthyl anthracene
  • An OLED was manufactured in the same manner as Example 1 except that dinaphthyl anthracene (DNA) instead of the compounds of the present invention as a host material at one cell of the vacuum vapor deposition apparatus and N 9 ,N 9 ,N 10 ,N 10 , 2,6-hexaphenylanthracene-9,10-diamine (Compound E ) as a dopant were used.
  • DNA dinaphthyl anthracene
  • Compound E 2,6-hexaphenylanthracene-9,10-diamine
  • the organic electroluminescent compounds according to the present invention realizes higher efficiency and color purity compared with the conventional material. It is possible to have good color purity due to the resonance of dimethylbenzo anthracene. Compound 5 has a characteristic of showing better luminous efficiency due to steric hindrance. Compound 58 has a great advantage in power consumption and operation life by introducing phenyl between substituents. It is possible to increase the operation life of the green organic electroluminescent compounds by lengthening the resonance length by introducing phenyl linked at the 2-position of anthracene in case of Compound 62 compared to Comparative Example 2. Accordingly, it is understood that the organic electroluminescent compounds according to the present invention may be used as an electroluminescent material having high efficiency and long lifespan.
  • the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.

Abstract

Disclosed are organic electroluminescent compounds and organic electroluminescent devices employing said compounds. The organic electroluminescent compounds of the invention are defined by chemical formula [1], Chemical Formula 1 The compounds, when used in an electron transport layer of an organic electroluminescent device, reduce power consumption and operation voltage of said device. Provided are novel organic electroluminescent compounds and an organic electroluminescent device using the same. Since the organic electroluminescent compound exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life and consuming less power due to improved power efficiency.

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 an electroluminescent material and an organic electroluminescent device using the same.
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].
An organic EL device is a device wherein, when charge is applied to an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole form a pair and then become extinct with emitting light. A device can be formed on a transparent flexible substrate such as plastics. The device can be operated at a lower voltage (not more than 10 V) with relatively lower power consumption but excellent color purity, as compared to a plasma display panel or an inorganic EL display. Since the organic electroluminescent (EL) devices can develop three colors (green, blue and red), they have been focused as full colored display devices for next generation.
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.
In general, the organic EL device commonly has a configuration of anode/hole injection layer (HIL)/hole transport layer (HTL)/emission material layer (EML)/electron transport layer (ETL)/electron injection layer (EIL)/cathode. Organic electroluminescent devices emitting blue, green or red light may be created depending on how to form the emission material layer.
In functional aspect, the electroluminescent materials may be divided into host materials and dopant materials. In general, an electroluminescent layer prepared by doping a dopant in a host is known to provide superior EL property. Recently, development of an organic EL device having high efficiency and long operation life is becoming an imminent task. Especially, considering the level of EL performance required for medium-to-large sized OLED panels, development of materials which are much superior to existing electroluminescent materials is urgently needed.
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 PCTKR2011001435-appb-I000001
Thus, the conventional materials do not form a thin film layer of host-dopant but is formed of a single layer. Also, it is determined that they have a difficulty in commercialization in view of color purity and efficiency. There is also a problem in that reliable data on long lifespan are not sufficient.
Also, for green fluorescent materials, a system for doping coumarin derivatives (Compound d, C545T), quinacridone derivatives (Compound e), DPT(Compound f) as a dopant with Alq as a host at several to several tens of % has been developed and widely used. These conventional electroluminescent materials show a performance of a level that they can be commercialized in an initial luminous efficiency. However, the initial luminous efficiency rapidly decreases and there is a problem in the operation life. Accordingly, the green fluorescent material has a limitation that it is difficult to be adopted in a high-performance panel of a large screen.
Figure PCTKR2011001435-appb-I000002
In addition, since the green fluorescent material does not allow an enough operation life to the OLED device, it is required to develop more stable host materials having superior performance.
Accordingly, an object of the present invention is to provide an organic electroluminescent compound having luminescence efficiency and device operation life improved over existing materials and having superior backbone with appropriate color coordinates in order to solve the aforesaid problems. Another object of the present invention is to provide an organic electroluminescent device employing the organic electroluminescent compound as an electroluminescent material.
In one general aspect, the present invention provides an organic electroluminescent compound represented by Chemical Formula 1 and an organic electroluminescent device using the same. With superior luminescence efficiency and excellent life property, the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life and consuming less power due to improved power efficiency.
[Chemical Formula 1]
Figure PCTKR2011001435-appb-I000003
wherein
R1 through R2 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s)or 5- to 7-membered heterocycloalkyl with or without substituent(s);
R3 through R11 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), cyano, nitro, hydroxyl, -NR21R22, -BR23R24, -PR25R26, -P(=O)R27R28, -SiR29R30R31 or -YR32;
R12 through R19 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, nitro, hydroxyl, -NR21R22, -BR23R24, -PR25R26, -P(=O)R27R28, -SiR29R30R31, -YR32, (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), or each of them may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring, wherein a carbon atom at the alicyclic ring or the mono- or polycyclic aromatic ring may be substituted with one or more heteroatom(s) selected from nitrogen, oxygen and sulfur;
Ar independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, nitro, hydroxyl, -NR21R22, -BR23R24, -PR25R26, -P(=O)R27R28, -SiR29R30R31, -YR32, (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), or (C2-C30)alkynyl with or without substituent(s);
A represents a chemical bond, (C6-C30)arylene with or without substituent(s), (C2-C30)heteroarylene with or without substituent(s) or (C6-C30)arylenethio with or without substituent(s);
B represents a chemical bond, (C2-C30)alkylene with or without substituent(s), (C6-C30)arylene with or without substituent(s), (C3-C30)heteroarylene with or without substituent(s), 5- to 7-membered heterocycloalkylene with or without substituent(s), 5- to 7-membered heterocycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkylene with or without substituent(s), (C3-C30)cycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C6-C30)arylene fused with one or more alicyclic ring(s) with or without substituent(s), (C2-C30)alkenylene with or without substituent(s), (C2-C30)alkynylene with or without substituent(s), (C6-C30)ar(C1-C30)alkylene with or without substituent(s), (C1-C30)alkylenethio with or without substituent(s), (C1-C30)alkyleneoxy with or without substituent(s), (C6-C30)aryleneoxy with or without substituent(s) or (C6-C30)arylenethio with or without substituent(s);
R21 through R32 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)heterocycloalkyl with or without substituent(s), or each of them may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
Y represents S or O;
a and b independently represent an integer from 1 to 3;
each A may be identical or different when a is 2 or greater, and each B may be identical or different when b is 2 or greater, and adjacent substituents may be linked to each other to form a ring; and
the heterocycloalkyl or heteroaryl includes one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P.
In the present invention, "alkyl", "alkoxy" and other substituents containing "alkyl" moiety include both linear and branched species. In the present invention, the cycloalkyl includes polycyclic hydrocarbon ring such as adamantyl with or without substituent(s) or (C7-C30)bicycloalkyl with or without substituent(s) as well as a monocyclic hydrocarbon 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 aryls linked by single bond(s). 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 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.
The '(C1-C30)alkyl' groups described herein may include (C1-C20)alkyl or (C1-C10)alkyl and the '(C6-C30)aryl' groups include (C6-C20)aryl or (C6-C12)aryl. The '(C3-C30)heteroaryl' groups include (C3-C20)heteroaryl or (C3-C12)heteroaryl and the '(C3-C30)cycloalkyl' groups include (C3-C20)cycloalkyl or (C3-C7)cycloalkyl. The '(C2-C30)alkenyl or alkynyl' group include (C2-C20)alkenyl or alkynyl, (C2-C10)alkenyl or alkynyl.
In the term 'substituted or unsubstituted (or with or without) substituent(s)' described herein, the term 'substituted' means that the unsubstituted substituent is further substituted with substituent(s). The substituent of R1 through R2, R3 through R11, R12 through R19, Ar, A, B and R21 through R32 may be further substituted by one or more substituent(s) selected from the group consisting of deuterium, halogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), RaRbRcSi-, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, -NRdRe, -BRfRg, -PRhRi, -P(=O)RjRk, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, RlX-, RmC(=O)-, RmC(=O)O-, carboxyl, nitro and hydroxyl; wherein Ra through Rl independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl; X represents S or O; and Rm represents (C1-C30)alkyl, (C1-C30)alkoxy, (C6-C30)aryl or (C6-C30)aryloxy.
The A represents a chemical bond, (C6-C30)arylene with or without substituent(s), (C2-C30)heteroarylene with or without substituent(s) or (C6-C30)arylenethio with or without substituent(s); B represents a chemical bond, (C6-C30)arylene with or without substituent(s), (C3-C30)heteroarylene with or without substituent(s), 5- to 7-membered heterocycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C6-C30)arylene fused with one or more alicyclic ring(s) with or without substituent(s), (C2-C30)alkenylene with or without substituent(s) or (C2-C30)alkynylene with or without substituent(s); and R1 through R19 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s) or -NR21R22 , or each of them may be linked to an adjacent substituent via C5 alkylene or
Figure PCTKR2011001435-appb-I000004
to form a ring.
Also, the Ar represents hydrogen, deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, fluoro, trimethylsilyl, triethylsilyl, tripropylsilyl, tri(t-butyl)silyl, t-butyldimethylsilyl, dimethylphenylsilyl, triphenylsilyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, n-pentoxy, i-pentoxy, n-hexyloxy, n-heptoxy, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, tetrazolyl, pyrazinyl, pyrimidyl, benzofuranyl, benzothiophenyl, pyrazolyl, indolyl, oxazolyl, benzothiazolyl, benzoxazolyl, dimethylamino, diphenylamino, monomethylamino, (4-t-butylphenyl)(phenyl)amino, monophenylamino, phenyloxy, phenylthio, triphenylmethyl, phenyl, naphthyl, biphenyl, phenanthryl, pyrenyl, fluoranthenyl, pyridyl, indenyl, triphenylenyl, tetrahydronaphthyl, 7H-benzo[c]fluorenyl, 7H-benzo[de]anthracenyl, tetrahydroquinolyl, anthracenyl, 7H-benzo[c]carbazolyl, ethynyl, ethenyl, quinolyl,
Figure PCTKR2011001435-appb-I000005
,
Figure PCTKR2011001435-appb-I000006
or
Figure PCTKR2011001435-appb-I000007
; wherein W and Z independently represent a chemical bond, -(CR61R62)m-, -N(R63)-, -S-, -O-, -Si(R64)(R65)- or -P(R66)-, with the proviso that they are not a chemical bond at the same time; R41 through R54 and R61 through R66 independently represent hydrogen, deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C3-C30)heteroaryl or (C3-C30)cycloalkyl, or each of them may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring; m represents an integer from 1 to 3; and Ar may be further substituted with one or more substituent(s) selected from the group consisting of deuterium, methyl, t-butyl, fluoro, methoxy, phenyl, triphenylsilyl, carbazolyl, 1-phenyl-1H-benzo[d]imidazole-2-yl, benzo[d]thiazole-2-yl, naphthyl, diphenylamino, phenylcarbonyl, (4-t-butylphenyl)(phenyl)amino, triphenylmethyl, (diphenylamino)phenyl and dibenzothienyl.
More specifically, the A is selected from a chemical bond or the following structures:
Figure PCTKR2011001435-appb-I000008
, and
Figure PCTKR2011001435-appb-I000009
may be selected from the following structures:
Figure PCTKR2011001435-appb-I000010
Figure PCTKR2011001435-appb-I000011
Figure PCTKR2011001435-appb-I000012
Figure PCTKR2011001435-appb-I000013
Figure PCTKR2011001435-appb-I000014
Figure PCTKR2011001435-appb-I000015
Figure PCTKR2011001435-appb-I000016
The organic electroluminescent compound is selected from the following compounds but the present invention is not limited by the compounds.
Figure PCTKR2011001435-appb-I000017
Figure PCTKR2011001435-appb-I000018
Figure PCTKR2011001435-appb-I000019
Figure PCTKR2011001435-appb-I000020
Figure PCTKR2011001435-appb-I000021
Figure PCTKR2011001435-appb-I000022
Figure PCTKR2011001435-appb-I000023
Figure PCTKR2011001435-appb-I000024
Figure PCTKR2011001435-appb-I000025
Figure PCTKR2011001435-appb-I000026
Figure PCTKR2011001435-appb-I000027
Figure PCTKR2011001435-appb-I000028
Figure PCTKR2011001435-appb-I000029
Figure PCTKR2011001435-appb-I000030
Figure PCTKR2011001435-appb-I000031
Figure PCTKR2011001435-appb-I000032
Figure PCTKR2011001435-appb-I000033
Figure PCTKR2011001435-appb-I000034
Figure PCTKR2011001435-appb-I000035
Figure PCTKR2011001435-appb-I000036
Figure PCTKR2011001435-appb-I000037
Figure PCTKR2011001435-appb-I000038
Figure PCTKR2011001435-appb-I000039
The organic electroluminescent compound according to the present invention may be prepared as shown in following Scheme 1.
[Scheme 1]
Figure PCTKR2011001435-appb-I000040
wherein
R1 through R2, R3 through R11, R12 through R19, A, B, Ar, a and b are the same as definition in the 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. The organic layer comprises an electroluminescent layer, in which the organic electroluminescent compounds of Chemical Formula 1 is used as a host or dopant material.
When the organic electroluminescent compounds of Chemical Formula 1 are used as the host, one or more dopant is included. The dopant 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 2:
[Chemical Formula 2]
Figure PCTKR2011001435-appb-I000041
wherein
Ar101 and Ar102 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s), (C6-C30)arylamino with or without substituent(s), (C1-C30)alkylamino, 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), or each of Ar101 and Ar102 may be linked 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;
Ar103 represents (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s) or a substituent selected from the following structures, when c is 1;
Figure PCTKR2011001435-appb-I000042
Ar103 represents (C6-C30)arylene with or without substituent(s), (C4-C30)heteroarylene with or without substituent(s) or a substituent selected from the following structures, when c is 2;
Figure PCTKR2011001435-appb-I000043
Ar104 and Ar105 independently represent (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);
R101 through R103 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C5-C30)heteroaryl with or without substituent(s), -NR111R112, -BR113R114, -PR115R116, -P(=O)R117R118, -SiR119R120R121 or -YR122;
R111 through R122 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)heterocycloalkyl with or without substituent(s), or each of R111 through R122 may be linked to an adjacent substituent to form a (C3-C30)aliphatic ring with or without substituent(s), a (C5-C30)heteroaliphatic ring with or without substituent(s), a (C6-C30)aromatic ring with or without substituent(s) or a (C6-C30)heteroaromatic ring with or without substituent(s);
Y represents S or O;
d represents an integer from 1 to 4; and
e represents an integer 0 or 1.
The dopant compounds of Chemical Formula 2 may be exemplified as Compounds having following structures but are not limited thereto:
Figure PCTKR2011001435-appb-I000044
Figure PCTKR2011001435-appb-I000045
Figure PCTKR2011001435-appb-I000046
Figure PCTKR2011001435-appb-I000047
Figure PCTKR2011001435-appb-I000048
Figure PCTKR2011001435-appb-I000049
Figure PCTKR2011001435-appb-I000050
Figure PCTKR2011001435-appb-I000051
Figure PCTKR2011001435-appb-I000052
Figure PCTKR2011001435-appb-I000053
Figure PCTKR2011001435-appb-I000054
When the organic electroluminescent compounds of Chemical Formula 1 are used as the dopant in the electroluminescent layer, one or more host is included. 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 Formulas 3 to 4:
[Chemical Formula 3]
(Ar11)f-L11-(Ar12)g
[Chemical Formula 4]
(Ar13)h-L12-(Ar14)i
wherein
L11 represents (C6-C60)arylene with or without substituent(s) or (C4-C60)heteroarylene with or without substituent(s);
L12 represents anthracenylene with or without substituent(s);
Ar11 through Ar14 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, nitro, -NR201R202, -BR203R204, -PR205R206, -P(=O)R207R208, R209R210R211Si-, R212X-, (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), or each of them may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring, wherein a carbon atom at the alicyclic ring or the mono- or polycyclic aromatic ring may be substituted with nitrogen;
R201 through R212 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s)or (C3-C30)heteroaryl with or without substituent(s);
X represents S or O;
the heterocycloalkyl and heteroaryl includes one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P;
f, g, h and i independently represent an integer of 0 to 4.
The host compounds of Chemical Formulas 3 to 4 may be exemplified as Compounds having following structures but are not limited thereto:
Figure PCTKR2011001435-appb-I000055
Figure PCTKR2011001435-appb-I000056
Figure PCTKR2011001435-appb-I000057
Figure PCTKR2011001435-appb-I000058
Figure PCTKR2011001435-appb-I000059
Figure PCTKR2011001435-appb-I000060
Figure PCTKR2011001435-appb-I000061
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.
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. The compound emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application No. 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 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 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 1
Figure PCTKR2011001435-appb-I000062
Preparation of Compound 1-1
After 7H-benzo[de]anthracen-7-one (40.0g, 0.17mol) was dissolved in diethyl ether (1000mL), AlCl3 (28g, 0.21mol) was slowly added thereto. After stirring the mixture for 15 minutes, the mixture was cooled to 0℃ and lithium aluminum hydride (LAH) (10g, 0.26mol) was slowly added thereto. After stirring the mixture under reflux for 1 hour, the mixture was slowly cooled to room temperature upon completion of the reaction. EA was slowly added to the mixture until the bubble stopped. After adding 6M HCl (100mL), the mixture was extracted with distilled water and ethyl acetate. After drying an organic layer with MgSO4 and removing solvent by a rotary type evaporator, Compound 1-1 (36.0g, 95%) was obtained by purification via column chromatography using dichloromethane and hexane as an eluent.
Preparation of Compound 1-2
After Compound 1-1 (36.0g, 0.16mol) was dissolved in DMSO (420mL), sodium tert-butoxide (113.0g, 1.2mol) was added at room temperature and stirred at 70℃ for 15 minutes. After methyl iodide (90 mL, 1.4mol) was slowly added thereto and stirred for 1 hour. Upon completion of the reaction, the reaction mixture was cooled to room temperature and distilled water was added thereto. After stirring the mixture for 20 minutes, a solid was produced and filtered. Compound 1-2 (26g, 63%) was obtained by recrystallizing the solid with methanol and acetone.
Preparation of Compound 1-3
Compound 1-2 (20g, 90mmol) was dissolved in DMF (300mL), and N-bromosuccinimide (16g, 90mmol) was slowly added thereto. The mixture was stirred at room temperature for one day. Upon completion of the reaction, the mixture was extracted with distilled water and EA. After drying an organic layer with MgSO4 and removing solvent by a rotary type evaporator, Target Compound 1-3 (26g, 91%) was obtained by purification via column chromatography using dichloromethane and hexane as an eluent.
Preparation of Compound 1
10-phenylanthracene-9-ylboronic acid (32g, 107mmol), Compound 1-3 (25g, 82mmol), Pd(PPh3)4 (6.2g, 5.4mmol) and Na2CO3 (17.4g, 164mmol) were dissolved in toluene/ethanol/distilled water 400mL/100mL/80mL and stirred at 100℃. Upon completion of the reaction, the mixture was extracted with distilled water and EA. After drying an organic layer with MgSO4 and removing solvent by a rotary type evaporator, Target Compound 1 (3g, 81%) was obtained by purification via column chromatography using dichloromethane and hexane as an eluent.
[Preparation Example 2] Preparation of Compound 57
Figure PCTKR2011001435-appb-I000063
4-(10-phenylanthracene-9-yl)phenylboronic acid (40g, 107mmol), Compound 1-3 (25g, 82mmol), Pd(PPh3)4 (6.2g, 5.4mmol) and Na2CO3 (17.4g, 164mmol) were dissolved in toluene/ethanol/distilled water 400mL/100mL/80mL and stirred at 100℃. Upon completion of the reaction, the mixture was extracted with distilled water and EA. After drying an organic layer with MgSO4 and removing solvent by a rotary type evaporator, Target Compound 57 (37g, 79%) was obtained by purification via column chromatography using dichloromethane and hexane as an eluent.
Organic electroluminescent compounds 1 to 73 were prepared according to the procedure of Preparation Examples 1 and 2. 1H NMR and MS/FAB data of thus prepared organic electroluminescent compounds are given in Table 1.
Table 1
Cmpd. 1H NMR(CDCl3, 200 MHz) MS/FAB
found calculated
1 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(9H, m), 7.51~7.52(4H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 496.64 496.22
2 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(8H, m), 7.58~7.59(3H, m), 7.71~7.73(2H, m), 7.91~7.92(5H, m), 7.98~8(4H, m), 8.39(1H, m) 546.70 546.23
3 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(8H, m), 7.55(2H, m), 7.61(1H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8.08(4H, m), 8.39~8.42(2H, m), 8.55(1H, m) 546.70 546.23
4 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(8H, m), 7.71(1H, m), 7.82~8(11H, m), 8.12(2H, m), 8.39(1H, m), 8.93(2H, m) 596.76 596.25
5 δ= 1.85(6H, s), 7(1H, m), 7.25(4H, m), 7.33~7.42(9H, m), 7.51~7.52(4H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 572.74 572.25
6 δ= 1.72(6H, s), 1.85(6H, s), 7(1H, m), 7.28~7.42(10H, m), 7.55(1H, m), 7.63(1H, m), 7.71~7.77(2H, m), 7.87~8(8H, m), 8.39(1H, m) 612.80 612.28
7 δ= 1.35(9H, s), 1.85(6H, s), 7(1H, m), 7.33~7.42(12H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 552.75 552.28
8 δ= 1.85(6H, s), 2.34(6H, s), 7(1H, m), 7.31~7.42(9H, m), 7.6(2H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 524.69 524.25
9 δ= 1.85(6H, s), 2.34(3H, s), 7(1H, m), 7.19(1H, m), 7.33~7.42(10H, m), 7.71(1H, m), 7.79(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 510.67 510.23
10 δ= 1.85(6H, s), 7(1H, m), 7.3~7.42(12H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 514.63 514.21
11 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(8H, m), 7.57(1H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39~8.42(2H, m), 8.7(1H, m), 9.24(1H, m) 497.63 497.21
12 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(9H, m), 7.48~7.57(7H, m), 7.7~7.71(2H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 572.74 572.25
13 δ= 1.85(6H, s), 7(1H, m), 7.25(4H, m), 7.33~7.41(15H, m), 7.71(1H, m), 7.85(2H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 648.83 648.28
14 δ= 1.85(6H, s), 7(1H, m), 7.33~7.39(25H, m), 7.71(1H, m), 7.89~7.91(6H, m), 7.98~8(2H, m), 8.39(1H, m) 755.03 754.31
15 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(9H, m), 7.51(2H, m), 7.59(2H, m), 7.71(1H, m), 7.79(2H, m), 7.91(4H, m), 7.98~8(4H, m), 8.39~8.4(3H, m) 622.79 622.27
16 δ= 1.85(6H, s), 3.83(3H, s), 7~7.05(3H, m), 7.33~7.42(8H, m), 7.68~7.71(3H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 526.67 526.23
17 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(8H, m), 7.5~7.52(2H, m), 7.71(1H, m), 7.86~7.91(5H, m), 7.98~8(5H, m), 8.39~8.45(2H, m) 602.78 602.21
18 δ= 1.85(6H, s), 7(1H, m), 7.32~7.42(11H, m), 7.66~7.71(2H, m), 7.81~7.91(7H, m), 7.98~8(2H, m), 8.39(1H, m) 586.72 586.23
19 δ= 1.85(6H, s), 7(1H, m), 7.25~7.42(11H, m), 7.5(1H, m), 7.63(1H, m), 7.71(1H, m), 7.9~8(7H, m), 8.12(1H, m), 8.39(1H, m), 8.55(1H, m) 585.73 585.25
20 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(11H, m), 7.48(1H, m), 7.71~7.84(6H, m), 7.91(4H, m), 7.98~8.12(5H, m), 8.39(1H, m) 678.80 678.25
21 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(8H, m), 7.71(5H, m), 7.82~7.91(6H, m), 7.98~8.04(3H, m), 8.12(1H, m), 8.18(1H, m), 8.39(1H, m) 620.78 620.25
22 δ= 0.66(6H, s), 1.85(6H, s), 7(1H, m), 7.33~7.42(9H, m), 7.52(1H, m), 7.58~7.61(2H, m), 7.71(1H, m), 7.8~7.91(7H, m), 7.98~8(2H, m), 8.39(1H, m) 628.87 628.26
23 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(8H, m), 7.58(1H, m), 7.71(1H, m), 7.79~7.8(2H, m), 7.9~8(8H, m), 8.1(2H, m), 8.39~8.42(3H, m) 620.78 620.25
24 δ= 1.85(6H, s), 7(1H, m), 7.25~7.42(11H, m), 7.5(1H, m), 7.63~7.71(4H, m), 7.79(2H, m), 7.91~8(7H, m), 8.12(1H, m), 8.39(1H, m), 8.55(1H, m) 661.83 661.28
25 δ= 1.78(6H, s), 1.85(6H, s), 7(1H, m), 7.14(1H, m), 7.33~7.42(8H, m), 7.51~7.54(2H, m), 7.69~7.71(2H, m), 7.83(1H, m), 7.91(4H, m), 7.98~8(3H, m), 8.09(1H, m), 8.15(1H, m), 8.39(1H, m), 8.52(1H, m) 662.86 662.30
26 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(10H, m), 7.51~7.52(8H, m), 7.66~7.71(4H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 648.83 648.28
27 δ= 1.85(6H, s), 7(1H, m), 7.22~7.25(4H, m), 7.33~7.5(11H, m), 7.58~7.59(3H, m), 7.71(1H, m), 7.85(2H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m), 8.56(1H, m) 688.86 688.29
28 δ= 1.85(6H, s), 7(1H, m), 7.25(2H, m), 7.33~7.42(8H, m), 7.53(2H, m), 7.71(1H, m), 7.85(2H, m), 7.91(4H, m), 7.98~8.01(3H, m), 8.18(1H, m), 8.39(1H, m) 629.81 629.22
29 δ= 1.69(6H, s), 1.85(6H, s), 6.94(1H, s), 7(1H, m), 7.22~7.42(12H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 562.74 562.27
30 δ= 1.72(6H, m), 1.85(4H, s), 2.74(4H, m), 6.88(1H, m), 6.98~7(2H, m), 7.15(1H, m), 7.33~7.42(8H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 550.73 550.27
31 δ= 1.78(6H, s), 1.85(6H, s), 7(1H, m), 7.24(1H, m), 7.33~7.44(9H, m), 7.51~7.54(2H, m), 7.61(1H, m), 7.71(1H, m), 7.91(4H, m), 7.98(1H, m), 7.99(1H, s), 8(1H, m), 8.09(1H, m), 8.39(1H, m), 8.52~8.56(2H, m) 662.86 662.30
32 δ= 1.85(12H, s), 7(2H, m), 7.33~7.42(12H, m), 7.71(2H, m), 7.91(4H, m), 7.98~8(4H, m), 8.39(2H, m) 662.86 662.30
33 δ= 1.72(12H, s), 1.85(6H, s), 7(1H, m), 7.24(1H, m), 7.33~7.44(9H, m), 7.61~7.63(2H, m), 7.69(1H, s), 7.71(1H, m), 7.77(2H, s), 7.77(0H, m), 7.91~8(7H, m), 8.09(1H, m), 8.39(1H, m) 728.96 728.34
34 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(8H, m), 7.71(1H, m), 7.82~7.91(8H, m), 7.98~8.04(3H, m), 8.12(2H, m), 8.18(1H, m), 8.39(1H, m), 8.93(2H, m), 9.15(1H, m) 646.82 646.27
35 δ= 1.85(6H, s), 1.96(2H, m), 2.76(2H, m), 3.06(2H, m), 6.55(1H, m), 6.72(1H, m), 7~7.07(3H, m), 7.33~7.42(8H, m), 7.71(1H, m), 7.88~7.9(4H, m), 7.98~8(2H, m), 8.39(1H, m) 551.72 551.26
36 δ= 1.72(6H, s), 1.85(6H, s), 6.55(2H, m), 6.73(2H, m), 7~7.05(5H, m), 7.33~7.42(8H, m), 7.71(1H, m), 7.88~7.9(4H, m), 7.98~8(2H, m), 8.39(1H, m) 627.81 627.29
37 δ= 1.85(6H, s), 7(1H, m), 7.25(4H, m), 7.33~7.42(8H, m), 7.55(2H, m), 7.61(1H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8.08(4H, m), 8.39~8.42(2H, m), 8.55(1H, m) 622.79 622.27
38 δ= 1.85(6H, s), 6.63(2H, m), 6.81(1H, m), 6.97~7(2H, m), 7.13~7.26(8H, m), 7.33~7.42(8H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 693.90 693.25
39 δ= 1.85(6H, s), 7(1H, m), 7.25(4H, m), 7.33~7.42(13H, m), 7.51~7.52(4H, m), 7.71(1H, m), 7.91(8H, m), 7.98~8(2H, m), 8.39(1H, m) 748.95 748.31
40 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(13H, m), 7.51~7.52(4H, m), 7.71(1H, m), 7.91(8H, m), 7.98~8(2H, m), 8.39(1H, m) 672.85 672.28
41 δ= 1.85(6H, s), 2.88(4H, m), 6.58(2H, m), 6.76(2H, m), 7~7.04(5H, m), 7.33~7.42(8H, m), 7.71(1H, m), 7.88~7.9(4H, m), 7.98~8(2H, m), 8.39(1H, m) 613.79 613.28
42 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(9H, m), 7.51~7.55(4H, m), 7.71(1H, m), 7.79(2H, m), 7.91(4H, m), 7.98~8.01(4H, m), 8.39(1H, m), 8.55(2H, m) 622.79 622.27
43 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(8H, m), 7.55(2H, m), 7.64(1H, m), 7.71~7.84(7H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 600.75 600.25
44 δ= 1.85(6H, s), 6.63(4H, m), 6.69(2H, m), 6.81(2H, m), 7(1H, m), 7.2(4H, m), 7.33~7.42(8H, m), 7.54(2H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 663.85 663.29
45 δ= 1.85(6H, s), 7(1H, m), 7.11(6H, m), 7.26~7.42(21H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 738.95 738.33
46 δ= 1.35(9H, s), 1.85(6H, s), 6.55(2H, m), 6.63(2H, m), 6.69(2H, m), 6.81(1H, m), 7~7.01(3H, m), 7.2(2H, m), 7.33~7.42(8H, m), 7.54(2H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 719.95 719.36
47 δ= 1.85(6H, s), 6.59~6.63(6H, m), 6.81(2H, m), 7(1H, m), 7.2(4H, m), 7.33~7.42(10H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 687.87 687.29
48 δ= 1.48(6H, m), 2.04(4H, m), 7(1H, m), 7.33~7.42(9H, m), 7.51~7.52(4H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 536.70 536.25
49 δ= 1.85(6H, s), 7(1H, m), 7.25(4H, m), 7.33~7.42(13H, m), 7.51~7.55(6H, m), 7.71(1H, m), 7.91(8H, m), 7.98~8.01(4H, m), 8.39(1H, m), 8.55(2H, m) 875.10 874.36
50 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(13H, m), 7.48~7.57(7H, m), 7.7~7.71(2H, m), 7.91(8H, m), 7.98~8(2H, m), 8.39(1H, m) 748.95 748.31
51 δ= 1.85(6H, s), 6.63(6H, m), 6.81(2H, m), 6.95~7(3H, m), 7.2(4H, m), 7.33~7.42(8H, m), 7.71~7.77(3H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 689.88 689.31
52 δ= 7(1H, m), 7.11(4H, m), 7.26~7.42(15H, m), 7.51~7.52(4H, m), 7.67(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 620.78 620.25
53 δ= 1.85(6H, s), 7(1H, m), 7.07(1H, m), 7.39~7.42(7H, m), 7.51~7.52(8H, m), 7.77(1H, m), 7.91~7.92(5H, m), 7.98~8(2H, m), 8.39(1H, m) 572.74 572.25
54 δ= 1.85(6H, s), 7(1H, m), 7.33~7.5(11H, m), 7.58~7.77(8H, m), 7.91(4H, m), 7.98~8(3H, m), 8.16~8.18(2H, m), 8.39(1H, m), 8.54(1H, m) 711.89 711.29
55 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(8H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 501.67 501.25
56 δ= 7(1H, m), 7.28~7.42(12H, m), 7.48~7.58(8H, m), 7.67~7.7(2H, m), 7.87~7.91(6H, m), 7.98~8(3H, m), 8.2(1H, m), 8.39~8.45(3H, m) 801.00 800.25
57 δ= 1.85(6H, s), 7(1H, m), 7.25(4H, m), 7.33~7.42(9H, m), 7.51~7.52(4H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 572.74 572.25
58 δ= 1.85(6H, s), 7(1H, m), 7.25(4H, m), 7.33~7.42(8H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 577.77 577.28
59 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(9H, m), 7.51~7.55(6H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8.01(4H, m), 8.39(1H, m), 8.55(2H, m) 622.79 622.27
60 δ= 1.85(6H, s), 7(1H, m), 7.25(4H, m), 7.33~7.42(9H, m), 7.6(1H, m), 7.71(1H, m), 7.78(1H, m), 7.91(4H, m), 7.98~8(3H, m), 8.06~8.1(2H, m), 8.39(1H, m) 623.78 623.26
61 δ= 1.6(2H, m), 1.85(6H, s), 1.91(2H, m), 2.85(2H, m), 4.13(1H, m), 6.92(4H, m), 7(1H, m), 7.25(4H, m), 7.33~7.42(8H, m), 7.71(1H, m), 7.89(2H, m), 7.96~8(4H, m), 8.39(1H, m) 626.83 626.30
62 δ= 1.85(6H, s), 7(1H, m), 7.25(4H, m), 7.33~7.42(8H, m), 7.51~7.52(8H, m), 7.61(1H, m), 7.71(1H, m), 7.91~8(5H, m), 8.13(1H, m), 8.39(1H, m) 648.83 648.28
63 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(9H, m), 7.48~7.57(7H, m), 7.7~7.71(2H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 572.74 572.25
64 δ= 1.85(6H, s), 7(1H, m), 7.33~7.42(9H, m), 7.51~7.52(4H, m), 7.69~7.71(2H, m), 7.91(4H, m), 8.03(2H, m), 8.39(1H, m), 8.49(1H, m), 8.78(1H, m) 573.72 573.25
65 δ= 1.85(6H, s), 1.91(4H, m), 4.13(2H, m), 6.92~6.97(5H, m), 7.03(1H, m), 7.33~7.41(9H, m), 7.51~7.52(4H, m), 7.71(1H, m), 7.81(1H, m), 7.89(2H, m), 7.96~8.02(3H, m) 626.83 626.30
66 δ= 1.85(6H, s), 7.17(1H, m), 7.25~7.26(5H, m), 7.33~7.41(10H, m), 7.51~7.52(4H, m), 7.71~7.75(2H, m), 7.91(6H, m) 622.79 622.27
67 δ= 1.85(6H, s), 7(1H, m), 7.33~7.41(15H, m), 7.59(2H, m), 7.71(1H, m), 7.91(4H, m), 7.98~8(2H, m), 8.39(1H, m) 604.80 604.22
68 δ= 1.85(6H, s), 7(1H, m), 7.25(4H, m), 7.33~7.42(7H, m), 7.51~7.52(12H, m), 7.61(2H, m), 7.71(1H, m), 7.97~8(4H, m), 8.13(2H, m), 8.39(1H, m) 724.93 724.31
69 δ= 1.85(6H, s), 6.63(8H, m), 6.81~6.83(6H, m), 7~7.03(3H, m), 7.2(8H, m), 7.33~7.42(4H, m), 7.58~7.59(3H, m), 7.71~7.75(4H, m), 7.92(1H, m), 7.98~8(4H, m), 8.39(1H, m) 881.11 880.38
70 δ= 1.85(6H, s), 6.63(4H, m), 6.81~6.83(4H, m), 7~7.03(3H, m), 7.2(4H, m), 7.33~7.42(6H, m), 7.49~7.5(4H, m), 7.58~7.59(3H, m), 7.71~7.77(8H, m), 7.84~7.92(5H, m), 7.98~8(4H, m), 8.39(1H, m) 981.23 980.41
71 δ= 1.85(6H, s), 6.63(8H, m), 6.81~6.83(6H, m), 7~7.03(3H, m), 7.2(8H, m), 7.33~7.42(4H, m), 7.55(2H, m), 7.61(1H, m), 7.71~7.75(3H, m), 7.98~8.08(4H, m), 8.39~8.42(2H, m), 8.55(1H, m) 881.11 880.38
72 δ= 1.35(18H, s), 1.85(12H, s), 6.55(4H, m), 6.63(4H, m), 6.81~6.83(4H, m), 7~7.06(8H, m), 7.2(4H, m), 7.33~7.42(7H, m), 7.58(1H, m), 7.71~7.75(4H, m), 7.82(1H, m), 7.98~8(2H, m), 8.39~8.41(2H, m), 8.48(1H, m) 1109.48 1108.57
73 δ= 1.35(18H, s), 1.85(6H, s), 6.55(4H, m), 6.63(4H, m), 6.81~6.83(4H, m), 7~7.03(7H, m), 7.2~7.25(8H, m), 7.33~7.42(5H, m), 7.51~7.52(4H, m), 7.71~7.75(3H, m), 7.98~8(2H, m), 8.39(1H, m) 1019.36 1018.52
[Example 1] 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. Compound 1 was placed in a cell of a vacuum vapor deposition apparatus as a host, and Compound D was placed in another cell as a dopant. The two materials were evaporated at different rates such that an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer through doping at 2 to 5 wt%.
Figure PCTKR2011001435-appb-I000064
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) of a following structure 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 was purified by vacuum sublimation at 10-6torr.
As a result, it was confirmed that current of 7.4 mA/cm2 flows at voltage of 7.0 V and a blue light of 1085 cd/m2 was emitted.
[Example 2]
An OLED device was manufactured as in Example 1 except that Compound 4 was added as a host material on the electroluminescent layer.
As a result, it was confirmed that current of 8.0 mA/cm2 flows at voltage of 7.2 V and a blue light of 1090 cd/m2 was emitted.
[Example 3]
An OLED device was manufactured as in Example 1 except that Compound 5 was added as a host material on the electroluminescent layer.
As a result, it was confirmed that current of 8.1 mA/cm2 flows at voltage of 7.4 V and a blue light of 1020 cd/m2 was emitted.
[Example 4]
An OLED device was manufactured as in Example 1 except that Compound 14 was added as a host material on the electroluminescent layer.
As a result, it was confirmed that current of 8.4 mA/cm2 flows at voltage of 7.8 V and a blue light of 1060 cd/m2 was emitted.
[Example 5]
An OLED device was manufactured as in Example 1 except that Compound 58 was added as a host material on the electroluminescent layer.
As a result, it was confirmed that current of 7.9 mA/cm2 flows at voltage of 7.2 V and a blue light of 1120 cd/m2 was emitted.
[Example 6]
An OLED device was manufactured as in Example 1 except that Compound 59 was added as a host material on the electroluminescent layer and N 9 ,N 9 ,N 10 ,N 10 ,2,6-hexaphenylanthracene-9,10-diamine(Compound E) was used as an electroluminescent dopant.
Figure PCTKR2011001435-appb-I000065
As a result, it was confirmed that current of 8.2 mA/cm2 flows at voltage of 7.2 V and a green light of 1480 cd/m2 was emitted.
[Example 7]
An OLED device was manufactured as in Example 6 except that Compound 53 was added as a host material on the electroluminescent layer.
As a result, it was confirmed that current of 8.9 mA/cm2 flows at voltage of 7.0 V and a green light of 1570 cd/m2 was emitted.
[Example 8]
An OLED device was manufactured as in Example 6 except that Compound 45 was added as a host material on the electroluminescent layer.
As a result, it was confirmed that current of 8.5 mA/cm2 flows at voltage of 6.8 V and a green light of 1500 cd/m2 was emitted.
[Example 9]
An OLED device was manufactured as in Example 6 except that Compound 62 was added as a host material on the electroluminescent layer.
As a result, it was confirmed that current of 8.7 mA/cm2 flows at voltage of 7.0 V and a green light of 1610 cd/m2 was emitted.
[Example 10]
An OLED device was manufactured as in Example 1 except that dinaphthyl anthracene (DNA) was added as a host material on the electroluminescent layer and Compound 69 was used as a dopant.
As a result, it was confirmed that current of 8.6 mA/cm2 flows at voltage of 7.2 V and a green light of 1530 cd/m2 was emitted.
[Example 11]
An OLED device was manufactured as in Example 1 except that dinaphthyl anthracene (DNA) was added as a host material on the electroluminescent layer and Compound 68 was used as a dopant.
As a result, it was confirmed that current of 8.7 mA/cm2 flows at voltage of 7.4 V and a green light of 1590 cd/m2 was emitted.
[Example 12]
An OLED device was manufactured as in Example 1 except that dinaphthyl anthracene (DNA) was added as a host material on the electroluminescent layer and Compound 73 was used as a dopant.
As a result, it was confirmed that current of 8.6 mA/cm2 flows at voltage of 7.4 V and a green light of 1500 cd/m2 was emitted.
[Comparative Example 1]
An OLED was manufactured in the same manner as Example 1 except that dinaphthyl anthracene (DNA) instead of the compounds of the present invention as a host material at one cell of the vacuum vapor deposition apparatus and Compound D as a dopant were used.
As a result, it was confirmed that current of 11.0 mA/cm2 flows at voltage of 6.7 V and a blue light of 1320 cd/m2 was emitted.
[Comparative Example 2]
An OLED was manufactured in the same manner as Example 1 except that dinaphthyl anthracene (DNA) instead of the compounds of the present invention as a host material at one cell of the vacuum vapor deposition apparatus and N 9 ,N 9 ,N 10 ,N 10 ,2,6-hexaphenylanthracene-9,10-diamine (Compound E) as a dopant were used.
As a result, it was confirmed that current of 11.0 mA/cm2 flows at voltage of 7.2 V and a blue light of 1793 cd/m2 was emitted.
As described above, the organic electroluminescent compounds according to the present invention realizes higher efficiency and color purity compared with the conventional material. It is possible to have good color purity due to the resonance of dimethylbenzo anthracene. Compound 5 has a characteristic of showing better luminous efficiency due to steric hindrance. Compound 58 has a great advantage in power consumption and operation life by introducing phenyl between substituents. It is possible to increase the operation life of the green organic electroluminescent compounds by lengthening the resonance length by introducing phenyl linked at the 2-position of anthracene in case of Compound 62 compared to Comparative Example 2. Accordingly, it is understood that the organic electroluminescent compounds according to the present invention may be used as an electroluminescent material having high efficiency and long lifespan.
Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having very superior operation life.

Claims (11)

  1. An organic electroluminescent compound represented by Chemical Formula 1:
    [Chemical Formula 1]
    Figure PCTKR2011001435-appb-I000066
    wherein
    R1 through R2 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s)or 5- to 7-membered heterocycloalkyl with or without substituent(s);
    R3 through R11 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), cyano, nitro, hydroxyl, -NR21R22, -BR23R24, -PR25R26, -P(=O)R27R28, -SiR29R30R31 or -YR32;
    R12 through R19 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, nitro, hydroxyl, -NR21R22, -BR23R24, -PR25R26, -P(=O)R27R28, -SiR29R30R31, -YR32, (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), or each of them may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring, wherein a carbon atom at the alicyclic ring or the mono- or polycyclic aromatic ring may be substituted with one or more heteroatom(s) selected from nitrogen, oxygen and sulfur;
    Ar independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, nitro, hydroxyl, -NR21R22, -BR23R24, -PR25R26, -P(=O)R27R28, -SiR29R30R31, -YR32, (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), or (C2-C30)alkynyl with or without substituent(s);
    A represents a chemical bond, (C6-C30)arylene with or without substituent(s), (C2-C30)heteroarylene with or without substituent(s) or (C6-C30)arylenethio with or without substituent(s);
    B represents a chemical bond, (C2-C30)alkylene with or without substituent(s), (C6-C30)arylene with or without substituent(s), (C3-C30)heteroarylene with or without substituent(s), 5- to 7-membered heterocycloalkylene with or without substituent(s), 5- to 7-membered heterocycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkylene with or without substituent(s), (C3-C30)cycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C6-C30)arylene fused with one or more alicyclic ring(s) with or without substituent(s), (C2-C30)alkenylene with or without substituent(s), (C2-C30)alkynylene with or without substituent(s), (C6-C30)ar(C1-C30)alkylene with or without substituent(s), (C1-C30)alkylenethio with or without substituent(s), (C1-C30)alkyleneoxy with or without substituent(s), (C6-C30)aryleneoxy with or without substituent(s) or (C6-C30)arylenethio with or without substituent(s);
    R21 through R32 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)heterocycloalkyl with or without substituent(s), or each of them may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
    Y represents S or O;
    a and b independently represent an integer from 1 to 3;
    each A may be identical or different when a is 2 or greater, and each B may be identical or different when b is 2 or greater, and adjacent substituents may be linked to each other to form a ring; and
    the heterocycloalkyl or heteroaryl includes one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P.
  2. The organic electroluminescent compound according to claim 1, wherein the substituent of R1 through R2, R3 through R11, R12 through R19, Ar, A, B and R21 through R32 may be further substituted by one or more substituent(s) selected from the group consisting of deuterium, halogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), RaRbRcSi-, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, -NRdRe, -BRfRg, -PRhRi, -P(=O)RjRk, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, RlX-, RmC(=O)-, RmC(=O)O-, carboxyl, nitro and hydroxyl; wherein Ra through Rl independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl; X represents S or O; and Rm represents (C1-C30)alkyl, (C1-C30)alkoxy, (C6-C30)aryl or (C6-C30)aryloxy.
  3. The organic electroluminescent compound according to claim 1, wherein A represents a chemical bond, (C6-C30)arylene with or without substituent(s), (C2-C30)heteroarylene with or without substituent(s) or (C6-C30)arylenethio with or without substituent(s); B represents a chemical bond, (C6-C30)arylene with or without substituent(s), (C3-C30)heteroarylene with or without substituent(s), 5- to 7-membered heterocycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkylene fused with one or more aromatic ring(s) with or without substituent(s), (C6-C30)arylene fused with one or more alicyclic ring(s) with or without substituent(s), (C2-C30)alkenylene with or without substituent(s) or (C2-C30)alkynylene with or without substituent(s); and R1 through R19 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s) or -NR21R22 , or each of them may be linked to an adjacent substituent via C5 alkylene or
    Figure PCTKR2011001435-appb-I000067
    to form a ring.
  4. The organic electroluminescent compound according to claim 1, wherein Ar represents hydrogen, deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, fluoro, trimethylsilyl, triethylsilyl, tripropylsilyl, tri(t-butyl)silyl, t-butyldimethylsilyl, dimethylphenylsilyl, triphenylsilyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, n-pentoxy, i-pentoxy, n-hexyloxy, n-heptoxy, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, tetrazolyl, pyrazinyl, pyrimidyl, benzofuranyl, benzothiophenyl, pyrazolyl, indolyl, oxazolyl, benzothiazolyl, benzoxazolyl, dimethylamino, diphenylamino, monomethylamino, (4-t-butylphenyl)(phenyl)amino, monophenylamino, phenyloxy, phenylthio, triphenylmethyl, phenyl, naphthyl, biphenyl, phenanthryl, pyrenyl, fluoranthenyl, pyridyl, indenyl, triphenylenyl, tetrahydronaphthyl, 7H-benzo[c]fluorenyl, 7H-benzo[de]anthracenyl, tetrahydroquinolyl, anthracenyl, 7H-benzo[c]carbazolyl, ethynyl, ethenyl, quinolyl,
    Figure PCTKR2011001435-appb-I000068
    ,
    Figure PCTKR2011001435-appb-I000069
    or
    Figure PCTKR2011001435-appb-I000070
    ; wherein W and Z independently represent a chemical bond, -(CR61R62)m-, -N(R63)-, -S-, -O-, -Si(R64)(R65)- or -P(R66)-, with the proviso that they are not a chemical bond at the same time; R41 through R54 and R61 through R66 independently represent hydrogen, deuterium, (C1-C30)alkyl, (C6-C30)aryl, (C3-C30)heteroaryl or (C3-C30)cycloalkyl, or each of them may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring; m represents an integer from 1 to 3; and Ar may be further substituted with one or more substituent(s) selected from the group consisting of deuterium, methyl, t-butyl, fluoro, methoxy, phenyl, triphenylsilyl, carbazolyl, 1-phenyl-1H-benzo[d]imidazole-2-yl, benzo[d]thiazole-2-yl, naphthyl, diphenylamino, phenylcarbonyl, (4-t-butylphenyl)(phenyl)amino, triphenylmethyl, (diphenylamino)phenyl and dibenzothienyl.
  5. The organic electroluminescent compound according to claim 1, wherein A is selected from a chemical bond or the following structures:
    Figure PCTKR2011001435-appb-I000071
    , and
    Figure PCTKR2011001435-appb-I000072
    is selected from the following structures:
    Figure PCTKR2011001435-appb-I000073
    Figure PCTKR2011001435-appb-I000074
    Figure PCTKR2011001435-appb-I000075
    Figure PCTKR2011001435-appb-I000076
    Figure PCTKR2011001435-appb-I000077
    Figure PCTKR2011001435-appb-I000078
    Figure PCTKR2011001435-appb-I000079
  6. An organic electroluminescent device comprising the organic electroluminescent compound according to any of claims 1 to 5.
  7. The organic electroluminescent device according to claim 6, which 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 5 and one or more dopant(s) represented by Chemical Formula 2:
    [Chemical Formula 2]
    Figure PCTKR2011001435-appb-I000080
    wherein
    Ar101 and Ar102 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s), (C6-C30)arylamino with or without substituent(s), (C1-C30)alkylamino, 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), or each of Ar101 and Ar102 may be linked 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;
    Ar103 represents (C6-C30)aryl with or without substituent(s), (C4-C30)heteroaryl with or without substituent(s) or a substituent selected from the following structures, when c is 1;
    Figure PCTKR2011001435-appb-I000081
    Ar103 represents (C6-C30)arylene with or without substituent(s), (C4-C30)heteroarylene with or without substituent(s) or a substituent selected from the following structures, when c is 2;
    Figure PCTKR2011001435-appb-I000082
    Ar104 and Ar105 independently represent (C6-C30)arylene with or without substituent(s) or (C4-C30)heteroarylene with or without substituent(s);
    R101 through R103 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C5-C30)heteroaryl with or without substituent(s), -NR111R112, -BR113R114, -PR115R116, -P(=O)R117R118, -SiR119R120R121 or -YR122;
    R111 through R122 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s) or (C3-C30)heterocycloalkyl with or without substituent(s), or each of R111 through R122 may be linked to an adjacent substituent to form a (C3-C30)aliphatic ring with or without substituent(s), a (C5-C30)heteroaliphatic ring with or without substituent(s), a (C6-C30)aromatic ring with or without substituent(s) or a (C6-C30)heteroaromatic ring with or without substituent(s);
    Y represents S or O;
    d represents an integer from 1 to 4; and
    e represents an integer 0 or 1.
  8. The organic electroluminescent device according to claim 6, which comprises a first electrode; a second electrode; and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer comprises organic electroluminescent compound and one or more host compound(s) represented by Chemical Formula 3 or 4:
    [Chemical Formula 3]
    (Ar11)f-L11-(Ar12)g
    [Chemical Formula 4]
    (Ar13)h-L12-(Ar14)i
    wherein
    L11 represents (C6-C60)arylene with or without substituent(s) or (C4-C60)heteroarylene with or without substituent(s);
    L12 represents anthracenylene with or without substituent(s);
    Ar11 through Ar14 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, nitro, -NR201R202, -BR203R204, -PR205R206, -P(=O)R207R208, R209R210R211Si-, R212X-, (C6-C30)ar(C1-C30)alkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C2-C30)alkynyl with or without substituent(s), or each of them may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring, wherein a carbon atom at the alicyclic ring or the mono- or polycyclic aromatic ring may be substituted with nitrogen;
    R201 through R212 independently represent (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s)or (C3-C30)heteroaryl with or without substituent(s);
    X represents S or O;
    the heterocycloalkyl and heteroaryl includes one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P;
    f, g, h and i independently represent an integer of 0 to 4.
  9. The organic electroluminescent device according to claim 7, wherein the organic layer further comprises one or more amine compound(s) selected from the group consisting of arylamine compounds and styrylaryl amine 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.
  10. The organic electroluminescent device according to claim 7, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
  11. The organic electroluminescent device according to claim 7, which is a white-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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