WO2011010840A1 - 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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WO2011010840A1
WO2011010840A1 PCT/KR2010/004693 KR2010004693W WO2011010840A1 WO 2011010840 A1 WO2011010840 A1 WO 2011010840A1 KR 2010004693 W KR2010004693 W KR 2010004693W WO 2011010840 A1 WO2011010840 A1 WO 2011010840A1
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substituent
alkyl
aryl
organic electroluminescent
group
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PCT/KR2010/004693
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French (fr)
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Chi Sik Kim
Sung Jin Eum
Young Jun Cho
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
Seung Soo Yoon
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Rohm And Haas Electronic Materials Korea Ltd.
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Publication of WO2011010840A1 publication Critical patent/WO2011010840A1/en

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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
    • C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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    • C07D471/00—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
    • 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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    • C07D471/12—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 three hetero rings
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    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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    • C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
    • C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
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    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • 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
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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    • 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
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    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms

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.
  • CBP is the most widely known as a host material for a phosphorescent material.
  • the OLED devices do not have satisfactory operation life. Therefore, development of more stable and higher-performance host materials is required.
  • the object of the present invention is to provide organic electroluminescent compounds having the backbone to provide better luminous efficiency and device life with appropriate color coordinate as compared to conventional host or dopant material, while overcoming the problems described above.
  • novel organic electroluminescent compounds represented by Chemical Formula 1 and an organic electroluminescent device using the same. Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property compared to the existing host material, it may be used to manufacture OLED devices having very superior operation life.
  • R 51 through R 58 and R 61 through R 63 are the same as R 1 through R 10 ;
  • R 21 through R 28 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),
  • R a , R b , R c and R d independently represent (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s)
  • Y represents S or O
  • R e and R f independently represent (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C6-C30)aryloxy with or without substituent(s);
  • n an integer 1 or 2.
  • alkyl alkoxy and other substituents containing “alkyl” moiety include both linear and branched species and "cycloalkyl” includes monocyclic hydrocarbons as well as polycyclic hydrocarbons such as adamantyl or bicycloalkyl.
  • aryl described herein means an organic radical derived from aromatic hydrocarbon via elimination of one hydrogen atom.
  • Each ring includes a monocyclic or fused ring system containing from 4 to 7, preferably from 5 to 6 cyclic atoms. A structure that one or more aryls are linked by a chemical bond is also included.
  • aryl examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl and fluoranthenyl, but they are not restricted thereto.
  • heteroaryl described herein means an aryl group containing from 1 to 4 heteroatom(s) selected from N, O and S for the aromatic cyclic backbone atoms, and carbon atom(s) for remaining aromatic cyclic backbone atoms.
  • the heteroaryl may be a 5- or 6-membered monocyclic heteroaryl or a polycyclic heteroaryl which is fused with one or more benzene ring(s), and may be partially saturated.
  • heteroaryl described herein includes a structure that one or more heteroaryls are linked by a chemical bond.
  • the heteroaryl groups may include divalent aryl groups of which the heteroatoms are oxidized or quarternized to form N-oxides, quaternary salts, or the like.
  • Specific examples of the heteroaryl include monocyclic heteroaryl groups such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl; polycyclic heteroaryl groups such as benzofuryl, benzothienyl, isobenzofuryl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benziso
  • 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 having one or more substituent(s) independently selected from 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), a 5- to 7-membered heterocycloalkyl, a 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), tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsily
  • the R 1 through R 10 , R 21 through R 28 , R 51 through R 58 and R 61 through R 63 are selected from hydrogen, halogen, alkyl such as methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, etc., aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl, etc., aryl fused with one or more cycloalkyl such as 1,2-dihydroacenaphthyl, heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thien
  • heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., aryloxy such as biphenyloxy, etc., arylthio such as biphenylthio, etc., aralkyl such as biphenylmethyl, triphenylmethyl, etc., carboxyl, nitro, , or hydroxyl, but are not limited thereto, and may be further substituted as shown in Chemical Formula 1.
  • the R 1 through R 10 are exemplified as following structures, but are not limited thereto.
  • R 41 through R 48 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
  • the R 1 through R 10 are selected from the following structures, but are not limited thereto.
  • the organic electroluminescent compound according to the present invention may be more specifically exemplified as following structures but is not limited thereto.
  • the organic electroluminescent compounds may be prepared as shown in following Reaction Scheme 1.
  • R 1 through R 10 are the same as definition in Chemical Formula 1.
  • an organic electroluminescent device which includes a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer includes one or more organic electroluminescent compound(s) represented by Chemical Formula 1.
  • the organic electroluminescent compounds are used as host material of an electroluminescent layer.
  • the organic layer includes one or more organic electroluminescent compound(s) and one or more dopant(s) represented by Chemical Formula 2.
  • the electroluminescent dopant applied to the organic electroluminescent device is not specifically limited but may be exemplified as compounds of the following Chemical Formula 2.
  • M 1 is a metal selected from a 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, (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(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), cyano or halogen;
  • R 220 through R 223 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s) or (C6-C30)aryl with or without (C1-C30)alkyl substituent(s);
  • R 224 and R 225 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or halogen, or R 224 and R 225 may be linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an alicylic ring or a mono- or polycyclic aromatic ring;
  • R 226 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;
  • R 227 through R 229 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or halogen;
  • R 231 through R 242 independently represent hydrogen, (C1-C30)alkyl, (C1-C30)alkoxy with or without halogen substituent(s), 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 R 207 or R 208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
  • M 1 of the Chemical Formula 2 is selected from Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag, and the compounds of the Chemical Formula 2 include the examples in KR Patent Application No. 10-2009-0037519, but is not limited thereto.
  • the organic electroluminescent device includes the organic electroluminescent compound of Chemical Formula 1 and includes one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds at the same time.
  • the arylamine compounds and styrylarylamine compounds include the examples in KR Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but are not limited thereto.
  • the organic layer may further include one or more metal(s) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s) as well as the organic electroluminescent compound of Chemical Formula 1.
  • the organic layer may simultaneously include the electroluminescent layer and a charge generating layer.
  • a white light-emitting organic electroluminescent device wherein the organic layer includes one or more organic electroluminescent layer(s) emitting blue, red or green light at the same time as well as the organic electroluminescent compound.
  • the organic electroluminescent compound according to the present invention has good luminescence efficiency and excellent life property, it may be used to manufacture an OLED device having very superior operation life.
  • organic electroluminescent compounds according to the present invention processes for preparing the same, and luminescence properties of devices employing the same will be described in detail hereinafter based on the representative compound for easy understanding.
  • the following examples are provided for illustrative purposes only and they are not intended to limit the scope of the present invention.
  • Compound 2-2 (8 g, 22.84 mmol, 62.04 %) was prepared using Compound 2-1 (13 g, 36.82 mmol) in the same manner as preparation of Compound 1-3 in Preparation Example 1.
  • Organic electroluminescent compounds 1 to 85 were prepared according to a process of Preparation Examples 1 and 2 and Table 1 shows 1 H NMR and MS/FAB of the prepared organic electroluminescent compounds.
  • An OLED device was manufactured using the electroluminescent material according to the present invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
  • an ITO substrate was equipped in a substrate folder of a vacuum vapor deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor deposition apparatus, which was then ventilated up to 10 -6 torr of vacuum in the chamber.
  • N,N' -bis( ⁇ -naphtyl)- 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 7 was placed in a cell of a vacuum vapor deposition apparatus as host, and Compound Iridium(III) tris(2-phenylpyridine) (Ir(ppy) 3 ) having a following structure 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 at 4 to 15 wt%.
  • Each compound used in the OLED was purified by vacuum sublimation at 10 -6 torr.
  • An OLED was manufactured as in Example 1 except that the hole blocking layer is not used.
  • An OLED was manufactured as in Example 2 except for using Compound 12 as host in the electroluminescent layer and bis(1-phenylisoquinolinato-N,C 2' )iridium(acetylacetonate) ((piq) 2 Ir(acac)) as dopant.
  • 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 was used as host material in a cell of the vacuum vapor deposition apparatus.
  • CBP 4,4'-Bis(carbazol-9-yl)-biphenyl
  • An OLED was manufactured in the same manner as Example 3 except that 4,4'-bis(carbazol-9-yl)biphenyl (CBP) instead of the compounds of the present invention was used as host material in a cell of the vacuum vapor deposition apparatus and Bis(2-methyl-8-quinolinato)( p -phenyl-phenolato)aluminum(III) (BAlq) is used as the hole blocking layer.
  • CBP 4,4'-bis(carbazol-9-yl)biphenyl
  • BAlq Bis(2-methyl-8-quinolinato)( p -phenyl-phenolato)aluminum(III)
  • Luminous efficiency of the OLED devices including the organic electroluminescent compound according to the present invention and the conventional electroluminescent compound manufactured in Examples 1 to 3 and Comparative Examples 1 and 2 was measured at 1,000 cd/m 2 . The result is given in Table 2.
  • the organic electroluminescent compounds 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 to 0.4 ⁇ 3.7 lm/W and improving power consumption.

Abstract

Provided herein are novel organic electroluminescent compounds and an organic electroluminescent device using the same More particularly, the organic electroluminescent compounds disclosed are represented by Chemical Formula (1).

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.
At present, CBP is the most widely known as a host material for a phosphorescent material. High-efficiency OLEDs using a hole blocking layer including BCP and BAlq and high-performance OLEDs using BAlq derivatives as a host were reported.
Although these materials provide good electroluminescence characteristics, they are disadvantageous in that degradation may occur during the high-temperature deposition process in vacuum because of low glass transition temperature and poor thermal stability. Since the power efficiency of an OLED is given by (p / voltage) current efficiency, the power efficiency is inversely proportional to the voltage. High power efficiency is required to reduce the power consumption of an OLED. Actually, OLEDs using phosphorescent materials provide much better current efficiency (cd/A) than those using fluorescent materials. However, when the existing materials such as BAlq, CBP, etc. are used as a host of the phosphorescent material, there is no significant advantage in power efficiency (lm/W) over the OLEDs using fluorescent materials because of high driving voltage.
In addition, the OLED devices do not have satisfactory operation life. Therefore, development of more stable and higher-performance host materials is required.
With intensive efforts to overcome the problems of conventional techniques as described above, the present inventors have invented novel electroluminescent compounds which realize organic electroluminescent devices having excellent luminous efficiency and noticeably improved life property.
The object of the present invention is to provide organic electroluminescent compounds having the backbone to provide better luminous efficiency and device life with appropriate color coordinate as compared to conventional host or dopant material, while overcoming the problems described above.
Provided are novel organic electroluminescent compounds represented by Chemical Formula 1 and an organic electroluminescent device using the same. Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property compared to the existing host material, it may be used to manufacture OLED devices having very superior operation life.
[Chemical Formula 1]
Figure PCTKR2010004693-appb-I000001
wherein
R1 through R10 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, NR21R22, BR23R24, PR25R26, P(=O)R27R28, RaRbRcSi-, RdY-, ReC(=O)-, RfC(=O)O-, (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 PCTKR2010004693-appb-I000002
, or
Figure PCTKR2010004693-appb-I000003
, 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 alicylic ring, a mono- or polycyclic aromatic ring or a mono- or polycyclic heteroaromatic ring;
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)-;
R51 through R58 and R61 through R63 are the same as R1 through R10;
the heterocycloalkyl or heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P;
R21 through R28 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), Ra, Rb, Rc and Rd independently represent (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s), Y represents S or O, and Re and Rf independently represent (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C6-C30)aryloxy with or without substituent(s); and
m represents an integer 1 or 2.
In the present invention, "alkyl", "alkoxy" and other substituents containing "alkyl" moiety include both linear and branched species and "cycloalkyl" includes monocyclic hydrocarbons as well as polycyclic hydrocarbons such as adamantyl or bicycloalkyl. The term "aryl" described herein means an organic radical derived from aromatic hydrocarbon via elimination of one hydrogen atom. Each ring includes a monocyclic or fused ring system containing from 4 to 7, preferably from 5 to 6 cyclic atoms. A structure that one or more aryls are linked by a chemical bond is also included. Specific examples of the aryl include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl and fluoranthenyl, but they are not restricted thereto.
The term "heteroaryl" described herein means an aryl group containing from 1 to 4 heteroatom(s) selected from N, O and S for the aromatic cyclic backbone atoms, and carbon atom(s) for remaining aromatic cyclic backbone atoms. The heteroaryl may be a 5- or 6-membered monocyclic heteroaryl or a polycyclic heteroaryl which is fused with one or more benzene ring(s), and may be partially saturated. In addition, the term "heteroaryl" described herein includes a structure that one or more heteroaryls are linked by a chemical bond.
The heteroaryl groups may include divalent aryl groups of which the heteroatoms are oxidized or quarternized to form N-oxides, quaternary salts, or the like. Specific examples of the heteroaryl include monocyclic heteroaryl groups such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl; polycyclic heteroaryl groups such as benzofuryl, benzothienyl, isobenzofuryl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinolizinyl, quinoxalinyl, carbazolyl, phenanthridinyl and benzodioxolyl; and corresponding N-oxides (for example, pyridyl N-oxide, quinolyl N-oxide) and quaternary salts thereof; but they are not restricted 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 having one or more substituent(s) independently selected from 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), a 5- to 7-membered heterocycloalkyl, a 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), tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR31R32, BR33R34, PR35R36, P(=O)R37R38, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro and hydroxyl; or that adjacent substituent(s) are linked together to form a ring; and the R31 through R38 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
The R1 through R10, R21 through R28, R51 through R58 and R61 through R63 are selected from hydrogen, halogen, alkyl such as methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl, octyl, etc., aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl, etc., aryl fused with one or more cycloalkyl such as 1,2-dihydroacenaphthyl, heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., heterocycloalkyl fused with one or more aromatic ring such as benzopyrrolidino, benzopiperidino, dibenzomorpholino, dibenzoazepino, etc., amino substituted by aryl such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl, triphenylenyl, etc. or heteroaryl such as dibenzothiophenyl, dibenzofuryl, carbazolyl, pyridyl, furyl, thienyl, quinolyl, triazinyl, pyrimidinyl, pyridazinyl, quinoxalinyl, phenanthrolinyl, etc., aryloxy such as biphenyloxy, etc., arylthio such as biphenylthio, etc., aralkyl such as biphenylmethyl, triphenylmethyl, etc., carboxyl, nitro,
Figure PCTKR2010004693-appb-I000004
,
Figure PCTKR2010004693-appb-I000005
or hydroxyl, but are not limited thereto, and may be further substituted as shown in Chemical Formula 1.
The R1 through R10 are exemplified as following structures, but are not limited thereto.
Figure PCTKR2010004693-appb-I000006
Figure PCTKR2010004693-appb-I000007
Figure PCTKR2010004693-appb-I000008
Figure PCTKR2010004693-appb-I000009
Figure PCTKR2010004693-appb-I000010
Figure PCTKR2010004693-appb-I000011
Figure PCTKR2010004693-appb-I000012
Figure PCTKR2010004693-appb-I000013
R71 through R172 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl, (C6-C30)aryl, (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(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), cyano, amino, (C1-C30)alkylamino, (C6-C30)arylamino, NR41R42, BR43R44, PR45R46, P(=O)R47R48, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro or hydroxyl, 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 alicylic ring or a mono- or polycyclic aromatic ring; and
R41 through R48 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
The R1 through R10 are selected from the following structures, but are not limited thereto.
Figure PCTKR2010004693-appb-I000014
Figure PCTKR2010004693-appb-I000015
Figure PCTKR2010004693-appb-I000016
Figure PCTKR2010004693-appb-I000017
Figure PCTKR2010004693-appb-I000018
Figure PCTKR2010004693-appb-I000019
Figure PCTKR2010004693-appb-I000020
The organic electroluminescent compound according to the present invention may be more specifically exemplified as following structures but is not limited thereto.
Figure PCTKR2010004693-appb-I000021
Figure PCTKR2010004693-appb-I000022
Figure PCTKR2010004693-appb-I000023
Figure PCTKR2010004693-appb-I000024
Figure PCTKR2010004693-appb-I000025
Figure PCTKR2010004693-appb-I000026
Figure PCTKR2010004693-appb-I000027
Figure PCTKR2010004693-appb-I000028
Figure PCTKR2010004693-appb-I000029
Figure PCTKR2010004693-appb-I000030
Figure PCTKR2010004693-appb-I000031
Figure PCTKR2010004693-appb-I000032
Figure PCTKR2010004693-appb-I000033
Figure PCTKR2010004693-appb-I000034
Figure PCTKR2010004693-appb-I000035
Figure PCTKR2010004693-appb-I000036
Figure PCTKR2010004693-appb-I000037
Figure PCTKR2010004693-appb-I000038
The organic electroluminescent compounds may be prepared as shown in following Reaction Scheme 1.
[Reaction Scheme 1]
Figure PCTKR2010004693-appb-I000039
wherein,
R1 through R10 are the same as definition in Chemical Formula 1.
Provided is an organic electroluminescent device, which includes a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer includes one or more organic electroluminescent compound(s) represented by Chemical Formula 1. The organic electroluminescent compounds are used as host material of an electroluminescent layer.
In the organic electroluminescent device, the organic layer includes one or more organic electroluminescent compound(s) and one or more dopant(s) represented by Chemical Formula 2. The electroluminescent dopant applied to the organic electroluminescent device is not specifically limited but may be exemplified as compounds of the following Chemical Formula 2.
[Chemical Formula 2]
M1L101L102L103
wherein
M1 is a metal selected from a 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 PCTKR2010004693-appb-I000040
Figure PCTKR2010004693-appb-I000041
Figure PCTKR2010004693-appb-I000042
Figure PCTKR2010004693-appb-I000043
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, (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, (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, (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 alicylic 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, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or halogen; and
Q represents
Figure PCTKR2010004693-appb-I000044
,
Figure PCTKR2010004693-appb-I000045
, or
Figure PCTKR2010004693-appb-I000046
, wherein R231 through R242 independently represent hydrogen, (C1-C30)alkyl, (C1-C30)alkoxy with or without halogen substituent(s), 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.
M1 of the Chemical Formula 2 is selected from Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag, and the compounds of the Chemical Formula 2 include the examples in KR Patent Application No. 10-2009-0037519, but is not limited thereto.
The organic electroluminescent device includes the organic electroluminescent compound of Chemical Formula 1 and includes one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds at the same time. The arylamine compounds and styrylarylamine compounds include the examples in KR Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but are not limited thereto.
The organic layer may further include one or more metal(s) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s) as well as the organic electroluminescent compound of Chemical Formula 1. The organic layer may simultaneously include the electroluminescent layer and a charge generating layer.
Provided is a white light-emitting organic electroluminescent device wherein the organic layer includes one or more organic electroluminescent layer(s) emitting blue, red or green light at the same time as well as the organic electroluminescent compound.
Since the organic electroluminescent compound according to the present invention has good luminescence efficiency and excellent life property, it may be used to manufacture an OLED device having very superior operation life.
The organic electroluminescent compounds according to the present invention, processes for preparing the same, and luminescence properties of devices employing the same will be described in detail hereinafter based on the representative compound for easy understanding. 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]
[Preparation Example 1] Preparation of Compound 1
Figure PCTKR2010004693-appb-I000047
Preparation of Compound 1-1
After 4H-1,2,4-triazole (10 g, 144.78 mmol) and MC (50 mL) were mixed together, a mixture of Br2 (48.5 g) and MC (50 mL) was slowly added thereto. After slowly adding 2M NaOH aqueous solution (217 mL), the mixture was stirred at room temperature for 2 hours and distilled water was added. After extracting with MC and drying with magnesium sulfate, distillation under reduced pressure followed by column separation yielded Compound 1-1 (17 g, 74.93 mmol, 52.03 %).
Preparation of Compound 1-2
Compound 1-1 (17 g, 74.93 mmol), iodobenzene (12.5 mL, 112.4 mmol), Cu (7.14 g, 112.4 mmol), K2CO3 (31.07 g, 224.8 mmol), 18-Crown-6 (1.58 g, 5.99 mmol), and 1,2-dichlorobenzene (100 mL) were mixed and stirred at 180 ℃ for 12 hours. The mixture was cooled at room temperature and organic solvent was distilled under reduced pressure. After adding distilled water, extracting with EA and drying with magnesium sulfate, distillation under reduced pressure followed by column separation yielded Compound 1-2 (14 g, 46.21 mmol, 62.16 %).
Preparation of Compound 1-3
Compound 1-2 (14 g, 46.21 mmol), phenylboronic acid (8.45 g, 69.31 mmol), Pd(PPh3)4 (1.6 g, 1.38 mmol), Na2CO3 (14.69 g, 138.6 mmol), distilled water (70 mL), and toluene (100 mL) were mixed and stirred under reflux. 12 hours later, the mixture was cooled to room temperature, extracted with EA and washed with distilled water. After drying with magnesium sulfate, distillation under reduced pressure followed by column separation yielded Compound 1-3 (12 g, 39.98 mmol, 84.78 %).
Preparation of Compound 1
Compound 1-3 (12 g, 39.98 mmol), carbazole (8.69 g, 51.97 mmol), Cu (3.81 g, 59.97 mmol), K2CO3 (16.57 g, 119.97 mmol), 18-crown-6 (0.84 g, 3.19 mmol), and 1,2-dichlorobenzene (100 mL) were mixed and stirred at 180 for 24 hours. The mixture was cooled at room temperature and organic solvent was distilled under reduced pressure. After adding distilled water, extracting with EA and drying with magnesium sulfate, distillation under reduced pressure followed by column separation yielded Compound 1 (9 g, 23.28 mmol, 58.24 %).
[Preparation Example 2] Preparation of Compound 43
Figure PCTKR2010004693-appb-I000048
Preparation of Compound 2-1
Compound 1-2 (17 g, 74.93 mmol), 1-iodonaphthalene (28.5 g, 112.4 mmol), Cu (7.14 g, 112.4 mmol), K2CO3 (31.07 g, 224.8 mmol), 18-Crown-6 (1.58 g, 5.99 mmol), and 1,2-dichlorobenzene (100 mL) were mixed and stirred at 180 for 12 hours. The mixture was cooled at room temperature and organic solvent was distilled under reduced pressure. After adding distilled water, extracting with EA and drying with magnesium sulfate, distillation under reduced pressure followed by column separation yielded Compound 2-1 (13 g, 36.82 mmol, 49.14 %).
Preparation of Compound 2-2
Compound 2-2 (8 g, 22.84 mmol, 62.04 %) was prepared using Compound 2-1 (13 g, 36.82 mmol) in the same manner as preparation of Compound 1-3 in Preparation Example 1.
Preparation of Compound 43
Compound 43 (6 g, 13.74 mmol, 60.18 %) was prepared using Compound 2-2 (8 g, 22.84 mmol) in the same manner as preparation of Compound 1 in Preparation Example 1.
Organic electroluminescent compounds 1 to 85 were prepared according to a process of Preparation Examples 1 and 2 and Table 1 shows 1H NMR and MS/FAB of the prepared organic electroluminescent compounds.
[Table 1]
Figure PCTKR2010004693-appb-I000049
Figure PCTKR2010004693-appb-I000050
Figure PCTKR2010004693-appb-I000051
Figure PCTKR2010004693-appb-I000052
Figure PCTKR2010004693-appb-I000053
Figure PCTKR2010004693-appb-I000054
[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 (15Ω/□) 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-naphtyl)-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 7 was placed in a cell of a vacuum vapor deposition apparatus as host, and Compound Iridium(III) tris(2-phenylpyridine) (Ir(ppy)3) having a following structure 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 at 4 to 15 wt%.
Subsequently,
bis(2-methyl-8-quinolinato)(p-phenylphenolato)aluminum(III) (BAlq) was vapor-deposited with a thickness of 5 nm as an hole blocking layer on the electroluminescent layer and tris(8-hydroxyquinoline)-aluminum(III) (Alq) was vapor-deposited with a thickness of 20 nm as an electron transport 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.
[Example 2] Manufacture of OLED using the organic electroluminescent compounds of the present invention
An OLED was manufactured as in Example 1 except that the hole blocking layer is not used.
[Example 3] Manufacture of OLED using the organic electroluminescent compounds of the present invention
An OLED was manufactured as in Example 2 except for using Compound 12 as host in the electroluminescent layer and bis(1-phenylisoquinolinato-N,C2')iridium(acetylacetonate) ((piq)2Ir(acac)) as dopant.
[Comparative Example 1] Electroluminescent properties of OLED using conventional electroluminescent material
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 was used as host material in a cell of the vacuum vapor deposition apparatus.
[Comparative Example 2] Electroluminescent properties of OLED using conventional electroluminescent material
An OLED was manufactured in the same manner as Example 3 except that 4,4'-bis(carbazol-9-yl)biphenyl (CBP) instead of the compounds of the present invention was used as host material in a cell of the vacuum vapor deposition apparatus and Bis(2-methyl-8-quinolinato)(p-phenyl-phenolato)aluminum(III) (BAlq) is used as the hole blocking layer.
Luminous efficiency of the OLED devices including the organic electroluminescent compound according to the present invention and the conventional electroluminescent compound manufactured in Examples 1 to 3 and Comparative Examples 1 and 2 was measured at 1,000 cd/m2. The result is given in Table 2.
[Table 2]
Figure PCTKR2010004693-appb-I000055
As shown in Table 2, 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 to 0.4~3.7 lm/W and improving power consumption.

Claims (10)

  1. An organic electroluminescent compound represented by Chemical Formula 1:
    Figure PCTKR2010004693-appb-I000056
    (1)
    wherein
    R1 through R10 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, NR21R22, BR23R24, PR25R26, P(=O)R27R28, RaRbRcSi-, RdY-, ReC(=O)-, RfC(=O)O-, (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 PCTKR2010004693-appb-I000057
    or
    Figure PCTKR2010004693-appb-I000058
    , 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 alicylic ring, a mono- or polycyclic aromatic ring or a mono- or polycyclic heteroaromatic ring;
    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)-;
    R51 through R58 and R61 through R63 are the same as R1 through R10;
    the heterocycloalkyl or heteroaryl may contain one or more heteroatom(s) selected from B, N, O, S, P(=O), Si and P;
    R21 through R28 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), Ra, Rb, Rc and Rd independently represent (C1-C30)alkyl with or without substituent(s) or (C6-C30)aryl with or without substituent(s), Y represents S or O, and Re and Rf independently represent (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C6-C30)aryloxy with or without substituent(s); and
    m represents an integer 1 or 2.
  2. The organic electroluminescent compound according to claim 1, wherein the substituent of R1 through R10, R21 through R28, R51 through R58 and R61 through R63 is substituted by one or more substituent(s) selected from a 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, (C3-C30)cycloalkyl fused with one or more aromatic ring(s), tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR31R32, BR33R34, PR35R36, P(=O)R37R38, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro and hydroxyl, or is linked to an adjacent substituent to form a ring; and
    R31 through R38 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
  3. The organic electroluminescent compound according to claim 1, wherein R1 through R10 are selected from the following structures:
    Figure PCTKR2010004693-appb-I000059
    Figure PCTKR2010004693-appb-I000060
    Figure PCTKR2010004693-appb-I000061
    Figure PCTKR2010004693-appb-I000062
    Figure PCTKR2010004693-appb-I000063
    Figure PCTKR2010004693-appb-I000064
    Figure PCTKR2010004693-appb-I000065
    Figure PCTKR2010004693-appb-I000066
    wherein
    R71 through R172 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl, (C6-C30)aryl, (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(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), cyano, amino, (C1-C30)alkylamino, (C6-C30)arylamino, NR41R42, BR43R44, PR45R46, P(=O)R47R48, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio, (C6-C30)aryloxy, (C6-C30)arylthio, (C1-C30)alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, (C6-C30)arylcarbonyloxy, (C6-C30)aryloxycarbonyloxy, carboxyl, nitro or hydroxyl, 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 alicylic ring or a mono- or polycyclic aromatic ring; and
    R41 through R48 independently represent (C1-C30)alkyl, (C6-C30)aryl or (C3-C30)heteroaryl.
  4. The organic electroluminescent compound according to claim 3, wherein R1 through R10 are selected from the following structures:
    Figure PCTKR2010004693-appb-I000067
    Figure PCTKR2010004693-appb-I000068
    Figure PCTKR2010004693-appb-I000069
    Figure PCTKR2010004693-appb-I000070
    Figure PCTKR2010004693-appb-I000071
    Figure PCTKR2010004693-appb-I000072
    Figure PCTKR2010004693-appb-I000073
  5. The organic electroluminescent compound according to claim 1, which is selected from the following compounds:
    Figure PCTKR2010004693-appb-I000074
    Figure PCTKR2010004693-appb-I000075
    Figure PCTKR2010004693-appb-I000076
    Figure PCTKR2010004693-appb-I000077
    Figure PCTKR2010004693-appb-I000078
    Figure PCTKR2010004693-appb-I000079
    Figure PCTKR2010004693-appb-I000080
    Figure PCTKR2010004693-appb-I000081
    Figure PCTKR2010004693-appb-I000082
    Figure PCTKR2010004693-appb-I000083
    Figure PCTKR2010004693-appb-I000084
    Figure PCTKR2010004693-appb-I000085
    Figure PCTKR2010004693-appb-I000086
    Figure PCTKR2010004693-appb-I000087
    Figure PCTKR2010004693-appb-I000088
    Figure PCTKR2010004693-appb-I000089
    Figure PCTKR2010004693-appb-I000090
    Figure PCTKR2010004693-appb-I000091
  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:
    M1L101L102L103 (2)
    wherein
    M1 is a metal selected from a 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 PCTKR2010004693-appb-I000092
    Figure PCTKR2010004693-appb-I000093
    Figure PCTKR2010004693-appb-I000094
    Figure PCTKR2010004693-appb-I000095
    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, (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, (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, (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 alicylic 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, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or halogen; and
    Q represents
    Figure PCTKR2010004693-appb-I000096
    ,
    Figure PCTKR2010004693-appb-I000097
    , or
    Figure PCTKR2010004693-appb-I000098
    , wherein R231 through R242 independently represent hydrogen, (C1-C30)alkyl, (C1-C30)alkoxy with or without halogen substituent(s), 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 a group consisting of arylamine compounds and styrylarylamine compounds, or one or more metal(s) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s).
  9. The organic electroluminescent device according to claim 7, wherein the organic layer comprises an electroluminescent layer or a charge generating layer.
  10. The organic electroluminescent device according to 7, which is a white lightemitting organic electroluminescent device wherein the organic layer comprises one or more organic electroluminescent layer(s) emitting blue, red or green light at the same time.
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