WO2011093609A1 - 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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WO2011093609A1
WO2011093609A1 PCT/KR2011/000333 KR2011000333W WO2011093609A1 WO 2011093609 A1 WO2011093609 A1 WO 2011093609A1 KR 2011000333 W KR2011000333 W KR 2011000333W WO 2011093609 A1 WO2011093609 A1 WO 2011093609A1
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substituent
alkyl
aryl
organic electroluminescent
independently represent
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PCT/KR2011/000333
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French (fr)
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Hye Mi Kim
Young Gil Kim
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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    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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Definitions

  • the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same, more particularly, to novel organic electroluminescent compounds used as an electroluminescent material and an organic electroluminescent device using the same as host.
  • 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 fluorescence 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.
  • 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.
  • a ring A represents or ;
  • X represents -C(R 12 )(R 13 )-, -N(R 14 )-, -S-, -O- or -Si(R 15 )(R 16 )-;
  • Ar 1 and Ar 2 independently represent (C6-C30)arylene with or without substituent(s) or (C3-C30)heteroarylene with or without substituent(s);
  • Ar 3 through Ar 5 independently represent (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s);
  • R 1 through R 16 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(s) 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, NR 21 R 22 , BR 23 R 24 , PR 25 R 26 , P(
  • R 21 through R 32 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);
  • Y represents S or O
  • R 41 through R 43 and R 51 through R 58 are the same as R 1 through R 16 ;
  • n an integer from 0 to 2;
  • a and b independently represent an integer from 0 to 4, and may be identical or different when a and b are larger than 2.
  • the may be exemplified by following structure but are not limited thereto.
  • R 21 through R 32 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);
  • Y represents S or O
  • alkyl in the present invention, “alkyl”, “alkoxy” and other substituents containing “alkyl” moiety include both linear and branched species.
  • the "cycloalkyl” includes hydrocarbon such as adamantyl or bicycloalkyl of a polycyclic ring as well as a monocyclic ring.
  • * marked in the chemical structure of the present invention means a portion linked inside the structure.
  • 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 chemical bond(s).
  • Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
  • 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.
  • heteroaryl may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with a benzene ring, and may be partially saturated.
  • the heteroaryl includes more than one heteroaryls linked by chemical bond(s).
  • the heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt.
  • monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, phenazinyl, phenothiazinyl, phenoxazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazo
  • 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.
  • the term 'substituted' means being further substituted by an unsubstituted substituent.
  • the substituent further substituted by Ar 1 through Ar 5 , R 1 through R 16 , R 21 through R 32 , R 41 through R 43 and R 51 through R 58 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), (C3-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C
  • The is selected from the following structures, but is not limited thereto.
  • R 81 through R 109 independently represent hydrogen, (C6-C30)aryl, (C3-C30)heteroaryl or tri(C6-C30)arylsilyl.
  • The is selected from the following structures, but is not limited thereto.
  • R 1 through R 16 independently represent any one selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, fluoro, cyano, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, n-pentoxy, i-pentoxy, n-hexyloxy, n-heptoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohepty
  • the R 1 through R 16 may be selected from following structures, but are not limited thereto.
  • the organic electroluminescent compound may be exemplified as 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.
  • an organic electroluminescent device which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compound(s) represented by Chemical Formula 1.
  • the organic layer may include one or more organic electroluminescent compounds of Chemical Formula 1 as an electroluminescent host and may include one or more dopant(s).
  • 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.
  • M 1 is selected from the group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 metals, and ligands L 101 , L 102 and L 103 are independently selected from the following structures:
  • R 201 through R 203 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl with or without (C1-C30)alkyl substituent(s) or halogen;
  • R 204 through R 219 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), mono- or di(C1-C30)alkylamino with or without substituent(s), mono- or di(C6-C30)arylamino with or without substituent(s), SF 5 , tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(
  • the dopant compounds of the Chemical Formula 2 may be exemplified by the compounds having following structures but are not limited thereto.
  • 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.
  • Organic electroluminescent Compounds 1 to 61 were prepared according to Preparation Examples 1 and 2. Table 1 shows 1 H NMR and MS/FAB of the prepared organic electroluminescent compounds.
  • An OLED device was manufactured as in Example 1 except that Compound 30 was added as a host material on the electroluminescent layer and Ir(ppy) 3 [tris(2-phenylpyridine)iridium] was used as an electroluminescent dopant.
  • the organic electroluminescent compounds according to the present invention have excellent properties compared with the conventional material.
  • the device using the organic electroluminescent compound according to the present invention as host material has excellent electroluminescent properties and drops driving voltage, thereby increasing power efficiency and improving power consumption.

Abstract

Provided are organic electroluminescent compounds of a fused pentacyclic structure of general formula I, and an organic electroluminescent device using said compounds. Since the organic electroluminescent compounds exhibit good luminous efficiency and lifespan, they may be used to manufacture OLED devices which have a superior operational lifetime and also have low power consumption due to the improved power efficiency of the compounds.

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 as host.
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 fluorescence 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. Accordingly, the organic electroluminescent devices are proper to be used as a next-generation flat display panel.
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.
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 PCTKR2011000333-appb-I000001
Wherein
a ring A represents
Figure PCTKR2011000333-appb-I000002
or
Figure PCTKR2011000333-appb-I000003
;
X represents -C(R12)(R13)-, -N(R14)-, -S-, -O- or -Si(R15)(R16)-;
Ar1 and Ar2 independently represent (C6-C30)arylene with or without substituent(s) or (C3-C30)heteroarylene with or without substituent(s);
Ar3 through Ar5 independently represent (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s);
R1 through R16 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(s) 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, NR21R22, BR23R24, PR25R26, P(=O)R27R28, R29R30R31Si-, R32Y-, (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),
Figure PCTKR2011000333-appb-I000004
,
Figure PCTKR2011000333-appb-I000005
or
Figure PCTKR2011000333-appb-I000006
, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring, a mono- or polycyclic aromatic ring or a mono- or polycyclic heteroaromatic ring;
R21 through R32 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);
Y represents S or O;
W represents -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- or -B(R58)-;
R41 through R43 and R51 through R58 are the same as R1 through R16;
the heterocycloalkyl, heteroaryl or heteroaromatic ring may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P;
m represents an integer from 0 to 2; and
a and b independently represent an integer from 0 to 4, and may be identical or different when a and b are larger than 2.
More specifically, the
Figure PCTKR2011000333-appb-I000007
may be exemplified by following structure but are not limited thereto.
Figure PCTKR2011000333-appb-I000008
wherein
R1 through R10 and R12 through R16 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), NR21R22, BR23R24, PR25R26, P(=O)R27R28, R29R30R31Si- or R32Y-, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring, a mono- or polycyclic aromatic ring or a mono- or polycyclic heteroaromatic ring;
R21 through R32 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);
Y represents S or O; and
the heteroaryl or heteroaromatic ring may contain 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 hydrocarbon such as adamantyl or bicycloalkyl of a polycyclic ring as well as a monocyclic ring. Also, * marked in the chemical structure of the present invention means a portion linked inside the structure.
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 chemical bond(s). Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto. 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. Further, the heteroaryl includes more than one heteroaryls linked by chemical bond(s). The heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, 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, phenazinyl, phenothiazinyl, phenoxazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, carborinyl, 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 being further substituted by an unsubstituted substituent. The substituent further substituted by Ar1 through Ar5, R1 through R16, R21 through R32, R41 through R43 and R51 through R58 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), (C3-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C3-C30)cycloalkyl fused with one or more aromatic ring(s), NR61R62, BR63R64, PR65R66, P(=O)R67R68, R69R70R71Si-, R72Z-, R73C(=O)-, R74C(=O)O-, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, carboxyl, nitro and hydroxyl, or may be linked to an adjacent substituent to form a ring; R61 through R72 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl; Z represents S or O; and R73 and R74 independently represent (C1-C30)alkyl, (C1-C30)alkoxy, (C6-C30)aryl or (C6-C30)aryloxy.
The
Figure PCTKR2011000333-appb-I000009
is selected from the following structures, but is not limited thereto.
Figure PCTKR2011000333-appb-I000010
wherein
R81 through R109 independently represent hydrogen, (C6-C30)aryl, (C3-C30)heteroaryl or tri(C6-C30)arylsilyl.
The
Figure PCTKR2011000333-appb-I000011
is selected from the following structures, but is not limited thereto.
Figure PCTKR2011000333-appb-I000012
Also, R1 through R16 independently represent any one selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, fluoro, cyano, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, n-pentoxy, i-pentoxy, n-hexyloxy, n-heptoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthasenyl, perylenyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, diphenyl triazinyl, phenothiazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyrazolyl, indolyl, N-phenylpyridoindolyl, N-phenylpyrazinoindolyl, carbazolyl, N-phenylcarbazolyl, N-phenylbenzocarbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tri(t-butyl)silyl, t-butyldimethylsilyl, dimethylphenylsilyl, triphenylsilyl or benzyl, but are not limited thereto.
The R1 through R16 may be selected from following structures, but are not limited thereto.
Figure PCTKR2011000333-appb-I000013
The organic electroluminescent compound may be exemplified as the following compounds but the present invention is not limited by the compounds.
Figure PCTKR2011000333-appb-I000014
Figure PCTKR2011000333-appb-I000015
Figure PCTKR2011000333-appb-I000016
Figure PCTKR2011000333-appb-I000017
Figure PCTKR2011000333-appb-I000018
Figure PCTKR2011000333-appb-I000019
Figure PCTKR2011000333-appb-I000020
Figure PCTKR2011000333-appb-I000021
Figure PCTKR2011000333-appb-I000022
Figure PCTKR2011000333-appb-I000023
Figure PCTKR2011000333-appb-I000024
Figure PCTKR2011000333-appb-I000025
Figure PCTKR2011000333-appb-I000026
The organic electroluminescent compound according to the present invention may be prepared as shown in following Scheme 1.
[Scheme 1]
Figure PCTKR2011000333-appb-I000027
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 may include one or more organic electroluminescent compounds of Chemical Formula 1 as an electroluminescent host and may include one or more dopant(s). 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]
M1L101L102L103
wherein
M1 is selected from the group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 metals, and ligands L101, L102 and L103 are independently selected from the following structures:
Figure PCTKR2011000333-appb-I000028
Figure PCTKR2011000333-appb-I000029
Figure PCTKR2011000333-appb-I000030
Figure PCTKR2011000333-appb-I000031
wherein
R201 through R203 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl with or without (C1-C30)alkyl substituent(s) or halogen; R204 through R219 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), mono- or di(C1-C30)alkylamino with or without substituent(s), mono- or di(C6-C30)arylamino with or without substituent(s), SF5, tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), cyano or halogen; R220 through R223 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without halogen substituent(s) or (C6-C30)aryl with or without (C1-C30)alkyl substituent(s); R224 and R225 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or halogen, or R224 and R225 may be linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring; R226 represents (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C5-C30)heteroaryl with or without substituent(s) or halogen; R227 through R229 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or halogen; and
Q represents
Figure PCTKR2011000333-appb-I000032
,
Figure PCTKR2011000333-appb-I000033
or
Figure PCTKR2011000333-appb-I000034
, wherein R231 through R242 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, halogen, (C6-C30)aryl with or without substituent(s), cyano or (C5-C30)cycloalkyl with or without substituent(s), or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring, or may be linked to R207 or R208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
The dopant compounds of the Chemical Formula 2 may be exemplified by the compounds having following structures but are not limited thereto.
Figure PCTKR2011000333-appb-I000035
Figure PCTKR2011000333-appb-I000036
Figure PCTKR2011000333-appb-I000037
Figure PCTKR2011000333-appb-I000038
Figure PCTKR2011000333-appb-I000039
Figure PCTKR2011000333-appb-I000040
Figure PCTKR2011000333-appb-I000041
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 13
Figure PCTKR2011000333-appb-I000042
Preparation of Compound 1-1
After 2-(phenylamino)benzoic acid (50 g, 0.23 mol) was dissolved in MeOH (1 L) and put into an ice bath, the mixture was stirred for 10 minutes. After slowly adding SOCl2 (60 mL, 0.58 mol) thereto at 0 ℃, the mixture was stirred under reflux for 12 hours at 90 ℃. Upon completion of the reaction, the reaction mixture was washed with distilled water and extracted with ethylacetate. After drying an organic layer with MgSO4 and removing solvent by a rotary type evaporator, Compound 1-1 (47 g, 92%) was obtained through purification by column chromatography using ethylacetate as a developing solvent.
Preparation of Compound 1-2
After Compound 1-1 (90 g, 0.3 mol) was added to THF (1.5 L), and MeMgBr(3.0M) (462 mL, 1.38 mol) was slowly added to the mixture, the resultant mixture was stirred for 12 hours at room temperature. Upon completion of the reaction, the reaction mixture was neutralized with distilled water and extracted with ethylacetate. After drying an organic layer with MgSO4 and removing solvent by the rotary type evaporator, Compound 1-2 (80 g, 90%) was obtained through purification by column chromatography using ethylacetate as a developing solvent.
Preparation of Compound 1-3
After Compound 1-2 (80 g, 0.35 mol) was added to H3PO4 (1.7 L), the mixture was stirred for 12 hours at room temperature. Upon completion of the reaction, the reaction mixture was neutralized with distilled water and the produced solid was filtered while being washed with water. The solid was dissolved with dichloromethane, extracted and neutralized with NaOH. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 1-3 (64 g, 87%) was obtained via recrystallization with hexane.
Preparation of Compound 1-4
Compound 1-3 (64 g, 0.30 mol), bromobenzene (52.8 g, 0.33 mol), Pd(OAc)2 (1.37 g, 6.11 mmol), P(t-Bu)3 (50%, 7.3 mL, 15.28 mmol) and NaOt-Bu (58 g, 0.61 mol) were dissolved in toluen (1.2 L), and the mixture was stirred for 12 hours at 120 ℃. Upon completion of the reaction, the reaction mixture was neutralized with distilled water and extracted with ethylacetate. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 1-4 (71 g, 81%) was obtained through purification by column chromatography using ethylacetate as a developing solvent.
Preparation of Compound 1-5
Compound 1-4 (20 g, 0.07 mol) was dissolved in DMF (800 mL) and the mixture was stirred for 10 minutes at 0 ℃. After slowly adding a solution that NBS (12.5 g, 0.07 mol) was dissolved in DMF (350 mL) thereto, the mixture was stirred for 6 hours at 0 ℃. Upon completion of the reaction, the reaction mixture was neutralized with distilled water and extracted with ethylacetate. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 1-5 (21 g, 84%) was obtained through purification by column chromatography using ethylacetate as a developing solvent.
Preparation of Compound 1-6
Compound 1-5 (20 g, 0.054 mol), 2-chloroaniline (8.4 g, 0.065 mol), Pd(OAc)2 (370 mg, 1.64 mmol), P(t-Bu)3 (50%, 3.6 mL, 5.49 mmol) and Cs2CO3 (35.7 g, 0.109 mol) were dissolved in toluen (300 mL), and the mixture was stirred for 4 hours at 120 ℃. Upon completion of the reaction, the reaction mixture was neutralized with distilled water and extracted with ethylacetate. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 1-6 (13.6 g, 60%) was obtained through purification by column chromatography using ethylacetate as a developing solvent.
Preparation of Compound 1-7
Compound 1-6 (12.6 g, 0.03 mol), Pd(OAc)2 (1.37 mg, 6.13 mmol), Di-tert-butyl(methyl)phosponium tetrafluoroborate (3 g, 12.26 mmol) and Cs2CO3 (50 g, 0.15 mol) were dissolved in DMA (240 mL), and the mixture was stirred for 4 hours at 190 ℃. Upon completion of the reaction, the reaction mixture was neutralized with distilled water and extracted with ethylacetate. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 1-7 (7 g, 70%) was obtained through purification by column chromatography using ethylacetate as a developing solvent.
Preparation of Compound 1-8
Compound 1-7 (13.2 g, 56.12 mmol), Cu (1.7 g, 28.06 mmol), K2CO3 (7.7 g, 56.12 mol) and 18-crown-6 (395 mg, 1.49 mmol) were dissolved in 1,2-dichlorobenzene (200 mL), and the mixture was stirred under reflux for 24 hours at 180 ℃. Upon completion of the reaction, cellite was extracted with methyl methylene chloride (MC) and MC was removed by the rotary type evaporator. 1,2-dichlorobenzene was removed by distillation. The mixture, from which the solvent was removed, was dissolved in MC again, neutralized with water and extracted with MC. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 1-8 (8 g, 80%) was obtained through purification by column chromatography using ethylacetate as a developing solvent.
Preparation of Compound 1-9
After Compound 1-8 (8 g, 15.10 mmol) was dissolved in THF (250 mL) and the mixture was cooled to -78 ℃, n-BuLi(2,5M) (9 mL, 22.66 mmol) was slowly added thereto. After the mixture was stirred for 1 hour while maintaining low temperature, B(OMe)3 (2.5 mL, 22.66 mmol) was added at -78 ℃ and the mixture was stirred for 1 hour. After reacting the mixture for 24 hours, 1M HCl was added thereto at 0 ℃, washed with distilled water 10 minutes later, and extracted with ethylacetate. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 1-9 (5 g, 67%) was obtained through purification by column chromatography.
Preparation of Compound 1-10
2,4,6-trichloropyrimidine (20 g, 0.109 mol), phenylboronic acid (29.2 g, 0.239 mol), Pd(PPh3)4 (6.3 g, 0.005 mol), Na2CO3(2M) (163 mL) and EtOH (163 mL) were dissolved in toluen (320 mL) and the mixture was heated at 120 ℃. When the reaction was completed after stirring the mixture for 3 hours, the reaction mixture was washed with distilled water and extracted with ethylacetate. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 1-10 (25 g, 86%) was obtained through purification by column chromatography.
Preparation of Compound 13
Compound 1-10 (2.7 g, 10.11 mmol), Compound 1-9 (5 g, 10.11 mmol), Pd(PPh3)4 (584 mg, 0.50 mmol), K2CO3(2M) (15 mL) and EtOH (15 mL) were dissolved in toluen (30 mL), and the mixture was heated at 120 ℃. After the mixture was stirred for 3 hours, the reaction was completed. The reaction mixture was washed with distilled water and extracted with ethylacetate. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 13 (5 g, 72%) was obtained through purification by column chromatography.
[Preparation Example 2] Preparation of Compound 48
Figure PCTKR2011000333-appb-I000043
Preparation of Compound 2-1
After Compound 1-5 (22 g, 61 mmol), methyl 2-amino benzoate (20 g, 136 mmol), palladium acetate (0.41 g, 1.8 mmol), tri-tert-butyl phosphine (1.69 g, 6.1 mmol) and cesium carbonate (39.4 g, 120 mmol) were dissolved in toluen (350 mL), the mixture was stirred under reflux for 12 hours at 100 ℃. Upon completion of the reaction, the reaction mixture was extracted with H2O/EA. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 2-2 (16 g, 61%) was obtained via column separation.
Preparation of Compound 2-2
After Compound 2-1 (16 g, 37 mmol) was dissolved in THF (180 mL) and 3M methylmagnesiumbromide (49.1 mL) was added to the mixture, the mixture was stirred for 4 hours at 60 ℃. After extracting with EA/H2O, drying an organic layer with MgSO4, and removing a solvent by the rotary type evaporator, Compound 2-2 (14 g, 87%) was obtained via silica filtration.
Preparation of Compound 2-3
After Compound 2-2 (14 g, 32.2 mmol) was dissolved in Phosphoric acid (300 mL), the mixture was stirred for 12 hours at room temperature. After extracting with EA/H2O, drying an organic layer with MgSO4, and removing a solvent by the rotary type evaporator, Compound 2-3 (10 g, 75%) was obtained via silica filtration.
Preparation of Compound 2-4
After Compound 2-3 (10 g, 24 mmol), 4-bromoiodobenzene (20.37 g, 72 mmol), copper powder (3.05 g, 48 mmol), 18-crown-6 (1.52 g, 5.8mmol) and potassium carbonate (9.95 g, 72 mmol) were dissolved in 1,2-dichlorobenzene (200 mL), the mixture was stirred under reflux for 12 hours at 180 ℃. After removing 1,2-dichlorobenzene by distillation, the reaction mixture was extracted with EA/H2O. After drying an organic layer with MgSO4 and removing a solvent by the rotary type evaporator, Compound 2-4 (6.5 g, 47%) was obtained via column separation.
Preparation of Compound 2-5
After Compound 2-4 (6.5 g, 11 mmol) was dissolved in THF (100 mL), the mixture was stirred for 1 hour by adding 2.5M n-Butyl lithium (5.91 mL) at -78 ℃. After tri-isopropyl borate (4.45 mL, 19 mmol) was added thereto, the mixture was stirred for 12 hours. After extracting with EA/H2O, drying an organic layer with MgSO4, and removing a solvent by the rotary type evaporator, Compound 2-5 (3 g, 41%) was obtained via recrystallization with dichloromethane/methanol.
Preparation of Compound 2-6
After 2,4-dichloropyrimidine (15 g, 100 mmol), phenyl boronic acid (12.28 g, 100 mL), Tetrakis(triphenylphosphine)palladium (5.82 g, 5 mmol), sodium carbonate (25.61 g, 240 mmol) and ethanol (200 mL) were dissolved in toluen (500 mL), the mixture was stirred under reflux for 3 hours at 70 ℃. After extracting with EA/H2O, drying an organic layer with MgSO4, and removing a solvent by the rotary type evaporator, Compound 2-6 (16 g, 83%) was obtained via column separation.
Preparation of Compound 48
After Compound 2-6 (0.75 g, 3.9 mmol), Compound 2-5 (2.53 g, 4.7mmol), Tetrakis(triphenylphosphine)palladium (0.23 g, 0.2 mmol), potassium carbonate (1.31 g, 9.4 mmol) and ethanol (50 mL) were dissolved in toluen (150 mL), the mixture was stirred under reflux for 5 hours at 120 ℃. After extracting with EA/H2O, drying an organic layer with MgSO4, and removing a solvent by the rotary type evaporator, Compound 48 (0.76 g, 30%) was obtained via column separation.
Organic electroluminescent Compounds 1 to 61 were prepared according to Preparation Examples 1 and 2. Table 1 shows 1H NMR and MS/FAB of the prepared organic electroluminescent compounds.
Table 1
Comp. 1H NMR(CDCl3, 200 MHz) MS/FAB
found calculated
1 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.11(1H, m), 7.2(2H, m), 7.29(1H, m), 7.41~7.54(9H, m), 7.55(1H, s), 7.63(1H, m), 8.08(1H, s), 8.12(1H, m), 8.3(2H, m), 8.6(1H, m) 603.75 603.27
2 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.29(1H, m), 7.41(2H, m), 7.5~7.51(5H, m), 7.55(1H, s), 7.63(1H, m), 8.08(1H, s), 8.12(1H, m), 8.28(4H, m) 605.73 605.26
3 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.29(1H, m), 7.41(2H, m), 7.5~7.51(5H, m), 7.55(1H, s), 7.63(1H, m), 7.79(4H, m), 8.08(1H, s), 8.12(1H, m), 8.63(1H, s) 604.74 604.26
4 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.29(1H, m), 7.32(1H, s), 7.41(2H, m), 7.5~7.51(5H, m), 7.55(1H, s), 7.63(1H, m), 7.79(2H, m), 8.08(1H, s), 8.12(1H, m), 8.28(2H, m) 604.74 604.26
5 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.11(1H, m), 7.2(2H, m), 7.29(1H, m), 7.41~7.54(9H, m), 7.55(1H, s), 7.63(1H, m), 8.08(1H, s), 8.12(1H, m), 8.3(2H, m), 8.6(1H, m) 603.75 603.27
6 δ = 1.72(6H, s), 6.61~6.63(3H, m), 6.81(1H, m), 7.2(2H, m), 7.29(1H, m), 7.36~7.41(4H, m), 7.5~7.52(9H, m), 7.55(1H, s), 7.61~7.63(2H, m), 8.08(1H, s), 8.12(1H, m), 8.28(4H, m) 681.83 681.29
7 δ = 1.72(6H, s), 6.55(1H, m), 6.73(1H, m), 7.02~7.05(2H, m), 7.29(1H, m), 7.41(4H, m), 7.5~7.51(9H, m), 7.55(1H, s), 7.63(1H, m), 7.79(4H, m), 7.85(1H, s), 8.08(1H, s), 8.12(1H, m), 8.28(4H, m) 759.90 759.31
8 δ = 1.72(6H, s), 6.61~6.63(3H, m), 6.81(1H, m), 7.2(2H, m), 7.36~7.41(5H, m), 7.51~7.52(12H, m), 7.55(1H, s), 7.61(1H, m), 7.69(1H, m), 7.77(1H, m), 7.87(1H, m), 8.08(1H, s), 8.28(4H, m) 757.92 757.32
9 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.4~7.41(3H, m), 7.51(4H, m), 7.55(2H, s), 7.55(0H, m), 7.67(2H, m), 8.08(1H, s), 8.16(2H, m), 8.28(4H, m) 655.79 655.27
10 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.41(2H, m), 7.51(4H, m), 7.55(1H, s), 7.63~7.67(4H, m), 8.08(1H, s), 8.16(1H, m), 8.28(4H, m), 8.54(1H, m) 655.79 655.27
11 δ = 1.72(6H, s), 6.55(1H, m), 6.62(1H, m), 6.7~6.73(2H, m), 7.02~7.05(2H, m), 7.29(1H, m), 7.41(2H, m), 7.5~7.51(5H, m), 7.55(2H, s), 7.55(0H, m), 7.63(1H, m), 8.07(1H, m), 8.08(1H, s), 8.12(1H, m), 8.28(4H, m) 606.72 606.25
12 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.29(1H, m), 7.41(2H, m), 7.5~7.51(5H, m), 7.55(1H, s), 7.63~7.68(3H, m), 7.79(4H, m), 8.08(1H, s), 8.12(1H, m), 8.23(1H, s), 8.28(2H, m) 680.84 680.29
13 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.29(1H, m), 7.41(2H, m), 7.5~7.51(5H, m), 7.55(1H, s), 7.63~7.68(3H, m), 7.79(6H, m), 8.08(1H, s), 8.12(1H, m), 8.23(1H, s) 680.84 680.29
14 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.29(1H, m), 7.41(2H, m), 7.5~7.51(5H, m), 7.55(1H, s), 7.63~7.68(3H, m), 7.79(2H, m), 8.08(1H, s), 8.12(1H, m), 8.28(4H, m) 681.83 681.29
15 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.29(1H, m), 7.41(2H, m), 7.5~7.51(5H, m), 7.55(1H, s), 7.63(1H, m), 7.79(4H, m), 7.88(1H, m), 7.96(1H, m), 8.08(1H, s), 8.12(1H, m), 8.58(1H, m), 8.59(1H, s) 681.83 681.29
16 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.29(1H, m), 7.37~7.51(17H, m), 7.55(4H, s), 7.55(0H, m), 7.61~7.63(2H, m), 7.76~7.79(3H, m), 7.88~7.89(2H, m), 7.96(1H, m), 8.08(1H, s), 8.12(1H, m), 8.58(1H, m), 8.59(1H, s) 940.21 939.38
17 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.29(1H, m), 7.37~7.5(14H, m), 7.55(4H, s), 7.55(0H, m), 7.61~7.63(2H, m), 7.76(1H, m), 7.89(1H, m), 7.96(1H, m), 8.08(1H, s), 8.12(1H, m), 8.57(1H, m) 787.03 786.32
18 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.29(1H, m), 7.41(1H, m), 7.5~7.51(3H, m), 7.55(1H, s), 7.56(1H, m), 7.63~7.68(3H, m), 7.79(4H, m), 8.08(1H, s), 8.12(1H, m), 8.29(1H, m) 604.74 604.26
19 δ = 1.72(6H, s), 6.4(2H, m), 6.55(1H, m), 6.73(1H, m), 7.02~7.05(2H, m), 7.29(1H, m), 7.45~7.54(10H, m), 7.55(1H, s), 7.58~7.63(3H, m), 8.08(1H, s), 8.12(1H, m), 8.3(4H, m) 603.75 603.27
20 δ = 1.72(6H, s), 6.55(1H, m), 6.73(1H, m), 7.02~7.05(2H, m), 7.29(1H, m), 7.41~7.51(10H, m), 7.55(1H, s), 7.58~7.63(3H, m), 8.08(1H, s), 8.12(1H, m), 8.28(4H, m) 605.73 605.26
21 δ = 1.72(6H, s), 6.55(1H, m), 6.73(1H, m), 7.02~7.05(2H, m), 7.29(1H, m), 7.41~7.51(10H, m), 7.55(1H, s), 7.58~7.63(3H, m), 7.79(4H, m), 7.85(1H, s), 8.08(1H, s), 8.12(1H, m) 604.74 604.26
22 δ = 1.72(6H, s), 6.55(1H, m), 6.69~6.73(3H, m), 7.02~7.05(2H, m), 7.29(1H, m), 7.41~7.51(10H, m), 7.55(1H, s), 7.58~7.63(3H, m), 7.79(4H, m), 7.9(2H, m), 8.08(1H, s), 8.12(1H, m), 8.23(1H, s) 680.84 680.29
23 δ = 1.72(6H, s), 6.29(1H, m), 6.55(1H, m), 6.73(1H, m), 6.8(1H, m), 7.02~7.05(2H, m), 7.29(1H, m), 7.41~7.52(9H, m), 7.55(1H, s), 7.58~7.63(3H, m), 7.88(2H, m), 8.08(1H, s), 8.12(1H, m), 8.23(1H, m), 8.81(2H, m) 603.75 603.27
24 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.81(1H, m), 7.19~7.38(11H, m), 7.45~7.5(5H, m), 7.55(1H, s), 7.58~7.63(5H, m), 7.94~7.98(3H, m), 8.08(1H, s), 8.12(2H, m), 8.55(2H, m) 780.95 780.33
25 δ = 1.72(6H, s), 6.61~6.63(3H, m), 6.81(1H, m), 7.2(2H, m), 7.29(1H, m), 7.41~7.51(10H, m), 7.55(1H, s), 7.58~7.63(4H, m), 7.72(1H, m), 8.08(1H, s), 8.12(1H, m), 8.28(4H, m) 681.83 681.29
26 δ = 1.72(6H, s), 6.61~6.63(3H, m), 6.81(1H, m), 7.2(2H, m), 7.25(1H, m), 7.29~7.41(14H, m), 7.55(1H, s), 7.58~7.63(5H, m), 7.88(1H, m), 7.94(1H, m), 8.05(2H, m), 8.08(1H, s), 8.12(2H, m), 8.55(1H, m) 767.96 767.33
27 δ = 1.72(6H, s), 6.61~6.63(3H, m), 6.81(1H, m), 7.2~7.33(6H, m), 7.41~7.51(10H, m), 7.55(1H, s), 7.58~7.63(5H, m), 7.72(1H, m), 7.94~7.98(2H, m), 8.08(1H, s), 8.12(1H, m), 8.28(4H, m), 8.55(1H, m) 847.02 846.35
28 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.41~7.51(9H, m), 7.55(1H, s), 7.58(2H, m), 7.69(1H, m), 7.77(1H, m), 7.87(1H, m), 8.08(1H, s), 8.28(4H, m) 681.83 681.29
29 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.32~7.38(3H, m), 7.45~7.5(3H, m), 7.55(1H, s), 7.58(2H, m), 7.66~7.69(2H, m), 7.77~7.89(5H, m), 8.08(1H, s) 616.75 616.25
30 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.45~7.52(5H, m), 7.55(1H, s), 7.58(3H, m), 7.69(1H, m), 7.77(1H, m), 7.87(1H, m), 7.98(1H, m), 8.08(1H, s), 8.2(1H, m), 8.41~8.45(2H, m) 632.81 632.23
31 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.29(1H, m), 7.45~7.5(7H, m), 7.55(1H, s), 7.58~7.63(5H, m), 7.69(1H, m), 7.77(2H, m), 7.87(1H, m), 8(1H, m), 8.08(1H, s), 8.12(1H, m), 8.18(1H, m) 691.86 691.30
32 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2~7.22(3H, m), 7.45~7.5(6H, m), 7.55(1H, s), 7.58(4H, m), 7.69(1H, m), 7.77(2H, m), 7.87(1H, m), 7.97~8(2H, m), 8.08(1H, s), 8.18(1H, m), 8.43(1H, m) 692.85 692.29
33 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.45~7.5(6H, m), 7.55(1H, s), 7.58(4H, m), 7.69(1H, m), 7.77(2H, m), 7.87(1H, m), 8(1H, m), 8.08(1H, s), 8.18(1H, m), 8.63(2H, m) 693.83 693.29
34 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.45~7.5(6H, m), 7.55(1H, s), 7.58~7.69(9H, m), 7.77(2H, m), 7.87(1H, m), 8(1H, m), 8.08(1H, s), 8.16~8.18(2H, m), 8.54(1H, m) 741.92 741.32
35 δ = 6.63(2H, m), 6.68(1H, s), 6.81(1H, m), 6.91(1H, s), 6.97(1H, m), 7.16~7.21(5H, m), 7.29(1H, m), 7.41(2H, m), 7.5~7.51(5H, m), 7.63(1H, m), 8.12(1H, m), 8.28(4H, m) 595.71 595.18
36 δ = 6.59~6.63(3H, m), 6.77(1H, m), 6.81(2H, s), 6.81(0H, m), 6.89~6.92(2H, m), 7.2(2H, m), 7.29(1H, m), 7.41(2H, m), 7.5~7.51(5H, m), 7.59(1H, s), 7.63(1H, m), 8.12(1H, m), 8.28(4H, m) 579.65 579.21
37 δ = 0.66(6H, s), 6.63(2H, m), 6.73(2H, m), 6.81(1H, m), 7.2~7.21(3H, m), 7.29~7.3(2H, m), 7.41(2H, m), 7.43(1H, s), 7.5~7.51(5H, m), 7.63(1H, m), 7.73(1H, s), 8.12(1H, m), 8.28(4H, m) 621.80 621.23
38 δ = 6.35(1H, s), 6.38(2H, m), 6.56(2H, m), 6.63(4H, m), 6.81(2H, m), 7.2(4H, m), 7.29(1H, m), 7.38(1H, s), 7.41(2H, m), 7.5~7.51(5H, m), 7.63(1H, m), 8.12(1H, m), 8.28(4H, m) 654.76 654.25
39 δ = 0.66(6H, s), 6.73(2H, m), 7.21(1H, m), 7.29~7.3(2H, m), 7.41(2H, m), 7.43(1H, s), 7.45~7.51(8H, m), 7.58~7.63(3H, m), 7.73(1H, s), 7.79(4H, m), 7.85(1H, s), 8.12(1H, m) 620.82 620.24
40 δ = 6.68(1H, s), 6.69(2H, m), 6.91(1H, s), 6.97(1H, m), 7.16~7.21(3H, m), 7.29(1H, m), 7.41~7.51(10H, m), 7.58~7.63(3H, m), 7.79(4H, m), 7.9(2H, m), 8.12(1H, m), 8.23(1H, s) 670.82 670.22
41 δ = 1.72(12H, s), 6.29(2H, s), 6.55(2H, m), 6.73(2H, m), 7.02~7.05(4H, m), 7.41(4H, m), 7.51(8H, m), 8.28(8H, m) 802.96 802.35
42 δ = 1.72(12H, s), 6.29(2H, s), 6.55(2H, m), 6.63(2H, m), 6.73(2H, m), 6.81(1H, m), 7.02~7.05(4H, m), 7.2(2H, m), 7.41(2H, m), 7.51(4H, m), 7.79(4H, m), 7.85(1H, s) 646.82 646.31
43 δ = 1.72(12H, s), 6.29(2H, s), 6.55(2H, m), 6.73(2H, m), 6.85(2H, m), 7.02~7.06(5H, m), 7.41(4H, m), 7.51~7.52(12H, m), 8.28(4H, m) 800.00 799.37
44 δ = 1.72(12H, s), 6.29(2H, s), 6.55(2H, m), 6.73(2H, m), 7~7.05(6H, m), 7.26(2H, m), 7.41~7.42(4H, m), 7.51(6H, m), 7.79(4H, m), 7.85(1H, s), 8.08(1H, m), 8.5(2H, m) 800.99 800.36
45 δ = 1.72(12H, s), 6.29(2H, s), 6.55(2H, m), 6.63(2H, m), 6.73(2H, m), 6.81(1H, m), 7.02~7.05(4H, m), 7.2(2H, m), 7.37~7.55(19H, m), 7.61(1H, m), 7.76(1H, m), 8.28(2H, m), 8.38(1H, m) 906.20 905.39
46 δ = 1.72(12H, s), 6.29(2H, s), 6.61~6.63(4H, m), 6.81(1H, m), 7.2(2H, m), 7.36~7.41(6H, m), 7.51~7.52(12H, m), 7.61(2H, m), 7.79(4H, m), 7.85(1H, s) 799.01 798.27
47 δ = 1.72(12H, s), 6.29(2H, s), 6.55(1H, m), 6.61~6.63(5H, m), 6.73(1H, m), 6.81(2H, m), 7.02~7.05(2H, m), 7.2(4H, m), 7.41(2H, m), 7.51(4H, m), 7.61(1H, m), 7.72(1H, m), 8.28(4H, m) 723.90 723.34
48 δ = 1.72(12H, s), 6.29(2H, s), 6.55(2H, m), 6.63(2H, m), 6.69~6.73(4H, m), 6.81(1H, m), 7.02~7.05(4H, m), 7.2(2H, m), 7.41(1H, m), 7.51~7.56(3H, m), 7.79(2H, m), 7.9(2H, m), 8.29(1H, m) 646.82 646.31
49 δ = 1.72(6H, s), 6.03(1H, s), 6.3(1H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 6.97~7.05(3H, m), 7.16~7.21(5H, m), 7.41(2H, m), 7.51(4H, m), 7.79(4H, m), 7.85(1H, s) 636.81 636.23
50 δ = 1.72(6H, s), 6.03(1H, s), 6.3(1H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 6.97~7.05(3H, m), 7.16~7.21(5H, m), 7.41(2H, m), 7.51(4H, m), 8.28(4H, m) 637.79 637.23
51 δ = 1.72(6H, s), 6.03(1H, s), 6.3(1H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 6.97~7.05(3H, m), 7.16~7.21(5H, m), 7.36(2H, m), 7.85(2H, m), 8.4(2H, m), 8.59(2H, m), 9.77(1H, s) 638.78 638.23
52 δ = 1.72(6H, s), 6(1H, s), 6.33(1H, s), 6.55~6.63(4H, m), 6.73~6.81(3H, m), 6.89~6.92(2H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.41(2H, m), 7.51(4H, m), 7.79(4H, m), 7.85(1H, s) 620.74 620.26
53 δ = 0.66(6H, s), 1.72(6H, s), 6.41(1H, s), 6.47(1H, s), 6.55(1H, m), 6.63(2H, m), 6.73(3H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2~7.21(3H, m), 7.3(1H, m), 7.41(2H, m), 7.51(4H, m), 8.28(4H, m) 663.88 663.28
54 δ = 1.72(12H, s), 5.61(1H, s), 6.55(2H, m), 6.63(2H, m), 6.73(2H, m), 6.74(1H, s), 6.81(1H, m), 7.02~7.05(4H, m), 7.2(2H, m), 7.41(2H, m), 7.51(4H, m), 8.28(4H, m) 647.81 647.30
55 δ = 0.66(12H, s), 6.59(2H, s), 6.63(2H, m), 6.73(4H, m), 6.81(1H, m), 7.2~7.21(4H, m), 7.3(2H, m), 7.41(2H, m), 7.51(4H, m), 8.28(4H, m) 679.96 679.26
56 δ = 1.72(6H, s), 6.03(1H, s), 6.3(1H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 6.97~7.05(3H, m), 7.16~7.21(5H, m), 7.41(2H, m), 7.51(4H, m), 8.28(4H, m) 637.79 637.23
57 δ = 0.66(6H, s), 1.72(6H, s), 6.41(1H, s), 6.47(1H, s), 6.55~6.63(4H, m), 6.73(3H, m), 6.81(1H, m), 6.89(1H, m), 7.02~7.05(2H, m), 7.16~7.33(8H, m), 7.44~7.5(2H, m), 7.63~7.64(2H, m), 7.94(1H, m), 8.12(1H, m), 8.55~8.57(2H, m) 751.99 751.31
58 δ = 1.72(6H, s), 6.52(1H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.29(1H, m), 7.41(2H, m), 7.5~7.51(5H, m), 7.63(1H, m), 8.12(1H, m), 8.28(4H, m), 8.54(1H, s) 605.73 605.26
59 δ = 1.72(6H, s), 6.52(1H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.29(1H, m), 7.41(2H, m), 7.5~7.51(5H, m), 7.63~7.68(3H, m), 7.79(6H, m), 8.12(1H, m), 8.23(1H, s), 8.54(1H, s) 680.84 680.29
60 δ = 1.72(6H, s), 6.52(1H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.29(1H, m), 7.41(2H, m), 7.5~7.51(5H, m), 7.63(1H, m), 7.79(4H, m), 7.88(1H, m), 7.96(1H, m), 8.12(1H, m), 8.54(1H, s), 8.58(1H, m), 8.59(1H, s) 681.83 681.29
61 δ = 1.72(6H, s), 6.55(1H, m), 6.63(2H, m), 6.73(1H, m), 6.81(1H, m), 7.02~7.05(2H, m), 7.2(2H, m), 7.41(2H, m), 7.48~7.52(8H, m), 7.55(1H, s), 7.57~7.58(2H, m), 7.69~7.7(2H, m), 7.77~7.79(5H, m), 7.87(1H, m), 7.98(1H, m), 8.08(1H, s), 8.2(1H, m), 8.41~8.45(2H, m), 8.63(1H, s) 863.08 8632.31
[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 20 was placed in a cell of a vacuum vapor deposition apparatus as a host, and Ir(ppy)3[tris(2-phenylpyridine)iridium] 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 4 to 10 wt%.
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 3.5 mA/cm2 flows at voltage of 6.6 V and a green light of 1270 cd/m2 was emitted.
[Example 2]
An OLED device was manufactured as in Example 1 except that Compound 30 was added as a host material on the electroluminescent layer and Ir(ppy)3[tris(2-phenylpyridine)iridium] was used as an electroluminescent dopant.
As a result, it was confirmed that current of 3.7 mA/cm2 flows at voltage of 7.2 V and a green light of 1040 cd/m2 was emitted.
[Example 3]
An OLED device was manufactured as in Example 1 except that Compound 40 was added as a host material on the electroluminescent layer and Ir(ppy)3[tris(2-phenylpyridine)iridium] was used as an electroluminescent dopant.
As a result, it was confirmed that current of 3.7 mA/cm2 flows at voltage of 6.7 V and a green light of 1170 cd/m2 was emitted.
[Example 4]
An OLED device was manufactured as in Example 1 except that Compound 48 was added as a host material on the electroluminescent layer and Ir(ppy)3[tris(2-phenylpyridine)iridium] was used as an electroluminescent dopant.
As a result, it was confirmed that current of 4.1 mA/cm2 flows at voltage of 6.9 V and a green light of 1120 cd/m2 was emitted.
[Comparative Example 1]
An OLED was manufactured in the same manner as Example 1 except that 4,4'-bis(carbazol-9-yl)biphenyl(CBP) instead of the compounds of the present invention as a host material at one cell of the vacuum vapor deposition apparatus, Ir(ppy)3[tris(2-phenyl pyridine)iridium] as a dopant and Bis(2-methyl-8-quinolinato)(p-phenyl-phenolato)aluminum(III) (BAlq) as a hole blocking layer were used.
As a result, it was confirmed that current of 3.8 mA/cm2 flows at voltage of 7.5 V and a green light of 1000 cd/m2 was emitted.
The organic electroluminescent compounds according to the present invention have excellent properties compared with the conventional material. In addition, the device using the organic electroluminescent compound according to the present invention as host material has excellent electroluminescent properties and drops driving voltage, thereby increasing power efficiency and improving power consumption.
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 (10)

  1. An organic electroluminescent compound represented by Chemical Formula 1:
    [Chemical Formula 1]
    Figure PCTKR2011000333-appb-I000044
    Wherein
    a ring A represents
    Figure PCTKR2011000333-appb-I000045
    or
    Figure PCTKR2011000333-appb-I000046
    ;
    X represents -C(R12)(R13)-, -N(R14)-, -S-, -O- or -Si(R15)(R16)-;
    Ar1 and Ar2 independently represent (C6-C30)arylene with or without substituent(s) or (C3-C30)heteroarylene with or without substituent(s);
    Ar3 through Ar5 independently represent (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s);
    R1 through R16 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(s) 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, NR21R22, BR23R24, PR25R26, P(=O)R27R28, R29R30R31Si-, R32Y-, (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),
    Figure PCTKR2011000333-appb-I000047
    ,
    Figure PCTKR2011000333-appb-I000048
    or
    Figure PCTKR2011000333-appb-I000049
    , or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring, a mono- or polycyclic aromatic ring or a mono- or polycyclic heteroaromatic ring;
    R21 through R32 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);
    Y represents S or O;
    W represents -(CR51R52)m-, -(R51)C=C(R52)-, -N(R53)-, -S-, -O-, -Si(R54)(R55)-, -P(R56)-, -P(=O)(R57)-, -C(=O)- or -B(R58)-;
    R41 through R43 and R51 through R58 are the same as R1 through R16;
    the heterocycloalkyl, heteroaryl or heteroaromatic ring may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P;
    m represents an integer from 0 to 2; and
    a and b independently represent an integer from 0 to 4, and may be identical or different when a and b are larger than 2.
  2. The organic electroluminescent compound according to claim 1, wherein
    Figure PCTKR2011000333-appb-I000050
    is selected from the following structures:
    Figure PCTKR2011000333-appb-I000051
    wherein
    R1 through R10 and R12 through R16 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), NR21R22, BR23R24, PR25R26, P(=O)R27R28, R29R30R31Si- or R32Y-, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring, a mono- or polycyclic aromatic ring or a mono- or polycyclic heteroaromatic ring;
    R21 through R32 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);
    Y represents S or O; and
    the heteroaryl or heteroaromatic ring may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P.
  3. The organic electroluminescent compound according to claim 1, wherein the substituent of Ar1 through Ar5, R1 through R16, R21 through R32, R41 through R43 and R51 through R58 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), (C3-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C3-C30)cycloalkyl fused with one or more aromatic ring(s), NR61R62, BR63R64, PR65R66, P(=O)R67R68, R69R70R71Si-, R72Z-, R73C(=O)-, R74C(=O)O-, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, carboxyl, nitro and hydroxyl, or may be linked to an adjacent substituent to form a ring; R61 through R72 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl; Z represents S or O; and R73 and R74 independently represent (C1-C30)alkyl, (C1-C30)alkoxy, (C6-C30)aryl or (C6-C30)aryloxy.
  4. The organic electroluminescent compound according to claim 1, wherein
    Figure PCTKR2011000333-appb-I000052
    is selected from the following structures:
    Figure PCTKR2011000333-appb-I000053
    wherein
    R81 through R109 independently represent hydrogen, (C6-C30)aryl, (C3-C30)heteroaryl or tri(C6-C30)arylsilyl.
  5. The organic electroluminescent compound according to claim 1, wherein R1 through R16 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, fluoro, cyano, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, n-pentoxy, i-pentoxy, n-hexyloxy, n-heptoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, biphenyl, fluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthasenyl, perylenyl, pyridyl, pyrrolyl, furanyl, thiophenyl, imidazolyl, benzoimidazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, quinolyl, triazinyl, diphenyl triazinyl, phenothiazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, pyrazolyl, indolyl, N-phenylpyridoindolyl, N-phenylpyrazinoindolyl, carbazolyl, N-phenylcarbazolyl, N-phenylbenzocarbazolyl, thiazolyl, oxazolyl, benzothiazolyl, benzoxazolyl, trimethylsilyl, triethylsilyl, tripropylsilyl, tri(t-butyl)silyl, t-butyldimethylsilyl, dimethylphenylsilyl, triphenylsilyl or benzyl.
  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]
    M1L101L102L103
    wherein
    M1 is selected from the group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 metals, and ligands L101, L102 and L103 are independently selected from the following structures:
    Figure PCTKR2011000333-appb-I000054
    Figure PCTKR2011000333-appb-I000055
    Figure PCTKR2011000333-appb-I000056
    Figure PCTKR2011000333-appb-I000057
    wherein
    R201 through R203 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl with or without (C1-C30)alkyl substituent(s) or halogen; R204 through R219 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), mono- or di(C1-C30)alkylamino with or without substituent(s), mono- or di(C6-C30)arylamino with or without substituent(s), SF5, tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), cyano or halogen; R220 through R223 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without halogen substituent(s) or (C6-C30)aryl with or without (C1-C30)alkyl substituent(s); R224 and R225 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or halogen, or R224 and R225 may be linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring; R226 represents (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C5-C30)heteroaryl with or without substituent(s) or halogen; R227 through R229 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or halogen; and
    Q represents
    Figure PCTKR2011000333-appb-I000058
    ,
    Figure PCTKR2011000333-appb-I000059
    or
    Figure PCTKR2011000333-appb-I000060
    , wherein R231 through R242 independently represent hydrogen, deuterium, (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, halogen, (C6-C30)aryl with or without substituent(s), cyano or (C5-C30)cycloalkyl with or without substituent(s), or each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring, or may be linked to R207 or R208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
  8. 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 compound and styrylaryl amine compounds or one or more metal(s) selected form the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements.
  9. The organic electroluminescent device according to claim 7, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
  10. 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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