WO2010056066A1 - Novel organometallic compounds for electroluminescence and organic electroluminescent device using the same - Google Patents

Novel organometallic compounds for electroluminescence and organic electroluminescent device using the same Download PDF

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WO2010056066A1
WO2010056066A1 PCT/KR2009/006693 KR2009006693W WO2010056066A1 WO 2010056066 A1 WO2010056066 A1 WO 2010056066A1 KR 2009006693 W KR2009006693 W KR 2009006693W WO 2010056066 A1 WO2010056066 A1 WO 2010056066A1
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alkyl
halogen
aryl
tri
group
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PCT/KR2009/006693
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French (fr)
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Hyun Kim
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
Seung Soo Yoon
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Gracel Display Inc.
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Priority to JP2011536250A priority Critical patent/JP5690276B2/en
Priority to CN2009801454526A priority patent/CN102216275A/en
Publication of WO2010056066A1 publication Critical patent/WO2010056066A1/en

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/08—Aza-anthracenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • 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
    • C07F7/0814—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 said ring is substituted at a C ring atom by Si
    • 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
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/381—Metal complexes comprising a group IIB metal element, e.g. comprising cadmium, mercury or zinc
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to an electroluminescent compound comprising a metal complex exhibiting excellent electrical conductivity and high luminous efficiency, and an electroluminescent device comprising the same as a host material.
  • electroluminescent material The most important factor that determines luminous efficiency of an OLED is the electroluminescent material . Atpresent, fluorescent materials are widely used for the electroluminescent material. But, phosphorescent materials are better when considering the electroluminescence mechanism. Theoretically, phosphorescent materials can improve the luminous efficiency by 4-fold.
  • iridium(III) complex-based phosphorescent materials are widely known. Such materials as (acac) Ir (btp) 2, Ir(ppy)3 and Firpic are known for red, green andblue colors, respectively. Recently, a lot of researches on phosphorescent materials are underway, especially in Japan, Europe and the US.
  • CBP is the most widely known as a host material for a phosphorescent material.
  • High-efficiency OLEDs using a hole blocking layer comprising BCP, BAIg, etc. are reported.
  • High-performance OLEDs using BAIq derivatives as a host were reported by Pioneer (Japan) and others.
  • the present invention provides an electroluminescent compound having a novel ligand metal complex with very superior electroluminescence characteristics and physical properties as compared to existing organic host materials as a backbone.
  • the present invention provides an electroluminescent device comprising the electroluminescent compound as a host material.
  • the present invention provides an organic solar cell comprising the electroluminescent compound.
  • the present invention relates to an electroluminescent compound represented by Chemical Formula 1 and an electroluminescent device comprising the same as a host material:
  • M represents a divalent or trivalent metal
  • n represents the cationic valence of M
  • Ri through R 8 independently represent hydrogen, (C1-C60) alkyl, halogen, cyano, (C3-C60) cycloalkyl, 5- or 6-memberedheterocycloalkyl containing one or more heteroatom (s) selected from N, O and S, (C7-C60)bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl,
  • aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but not limited thereto.
  • the naphthyl includes 1-naphthyl and 2-naphthyl
  • the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl
  • the fluorenyl includes all of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • heteroaryl means an aryl group containing 1 to 4 heteroatom (s) selected from N, 0, S and Si as aromatic ring backbone atom(s), other remaining aromatic ring backbone atoms being carbon.
  • the heteroaryl includes a divalent aryl group wherein the heteroatom (s) in the ring may be oxidized or quaternized to form, for example, N-oxide or quaternary salt .
  • monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, is
  • the substituents including " (C1-C60) alkyl” moiety may have 1 to 60 carbon atoms, 1 to 20 carbon atoms, or 1 to 10 carbon atoms.
  • the substituents including " (C6-C60) aryl” moiety may have 6 to 60 carbon atoms, 6 to 20 carbon atoms, or 6 to 12 carbon atoms.
  • the substituents including " (C3-C60) heteroaryl” moiety may have 3 to 60 carbon atoms, 4 to 20 carbon atoms, or 4 to 12 carbon atoms.
  • (C3-C60) cycloalkyl moiety may have 3 to 60 carbon atoms, 3 to 20 carbon atoms, or 3 to 7 carbon atoms.
  • the substituents including " (C2-C60) alkenyl or alkynyl” moiety may have 2 to 60 carbon atoms, 2 to 20 carbon atoms, or 2 to 10 carbon atoms.
  • Ri through R 8 may independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, trifluoromethyl, perfluoroethyl, perfluorobutyl, chloro, fluoro, cyano, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, pyridyl, furyl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl,
  • electroluminescent compound represented by Chemical Formula 1 may be exemplified by following compounds, but not limited thereto:
  • the present invention further provides an organic solar cell.
  • the organic solar cell according to the present invention comprises one or more electroluminescent compound (s) represented by Chemical Formula 1.
  • the present invention further provides an electroluminescent device.
  • the electroluminescent device according to the present invention 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 electroluminescent compound (s) represented by Chemical Formula 1.
  • the organic layer further comprises an electroluminescent layer.
  • the electroluminescent layer comprises one or more electroluminescent compound (s) represented by Chemical Formula 1, as an electroluminescent host, and one or more electroluminescent dopant (s) .
  • the electroluminescent dopant used in the electroluminescent device according to the present invention is not particularly limited, but may be exemplified by the compounds represented by 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;
  • ligands L 101 , L 102 and L 103 are independently selected from the following structures:
  • Rn through R 13 independently represent hydrogen, (C1-C60) alkyl with or without halogen substituent, (C6-C60)aryl with or without (C1-C60) alkyl substituent or halogen;
  • Ri 4 through R 29 independently represent hydrogen, (C1-C60 ) alkyl, (Cl-C30)alkoxy, (C3-C60) cycloalkyl, (C2-C30) alkenyl, (C6-C60) aryl, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino, SF 5 , tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, cyano or halogen, and the alkyl, cycloalkyl, alkenyl or aryl of Ri 4 through R 29 may be further substituted by one or more substituent (s) selected from (C1-C60) alkyl, (C6-C60) aryl and halogen;
  • R 30 through R 33 independently represent hydrogen, (C1-C60) alkyl with or without halogen substituent or (C6-C60)aryl with or without (C1-C60) alkyl substituent;
  • R 34 and R 35 independently represent hydrogen, (C1-C60) alkyl, (C6-C60) aryl or halogen, OrR 34 and R 35 may be linked via (C3-C12) alkylene or (C3-C12) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring, and the alkyl or aryl of R 34 and R 35 , or the alicyclic ring or the monocyclic or polycyclic aromatic ring formed as they are linked via (C3-C12) alkylene or
  • (C3-C12) alkenylene with or without a fused ring may be further substituted by one or more substituent (s) selected from (C1-C60) alkyl with or without halogen substituent, (C1-C30) alkoxy, halogen, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl and (C6-C60) aryl;
  • R 36 represents (C1-C60) alkyl, (C6-C60) aryl, (C5-C60) heteroaryl containing one or more heteroatom (s) selected from N, 0 and S or halogen;
  • R 37 through R 39 independently represent hydrogen, (C1-C60) alkyl,
  • R 40 and R 41 independently represent hydrogen, (C1-C20) alkyl with or without halogen substituent, (C6-C20) aryl, halogen, cyano, tri (C1-C20) alkylsilyl, di (C1-C20) alkyl (C6-C20) arylsilyl, tri (C6-C20)arylsilyl, (C1-C20) alkoxy, (C1-C20) alkylcarbonyl, (C6-C20) arylcarbonyl, di (C1-C20) alkylamino or di (C6-C20) arylamino, or R 40 and R 4I may be linked via (C3-C12 ) alkylene or (C3-C12) alkenylene with or without
  • (C3-C12) alkylene or (C3-C12) alkenylene with or without a fused ring may be further substituted by one or more substituent (s) selected from (C1-C20) alkyl with or without halogen substituent, halogen, cyano, tri (C1-C20) alkylsilyl, di (C1-C20) alkyl (C6-C20) arylsilyl, tri (C6-C20) arylsilyl, (C1-C20) alkoxy, (C1-C20) alkylcarbonyl, (C6-C20) arylcarbonyl, di (C1-C20) alkylamino, di (C6-C20) arylamino, phenyl, naphthyl, anthryl, fluorenyl and spirobifluorenyl, or may be further substituted by phenyl or fluorenyl with one or more substituent (s) selected
  • R 42 through R 49 independently represent hydrogen, (C1-C20) alkyl with or without halogen substituent, (C1-C20) alkoxy, (C3-C12) cycloalkyl, halogen, cyano, (C6-C20) aryl, (C4-C20) heteroaryl, tri (C1-C20) alkylsilyl, di (Cl-C20)alkyl (C6-C20) arylsilyl or tri (C6-C20) arylsilyl; and
  • R 5i through R 62 fe independently represent hydrogen, (C1-C60) alkyl with or without halogen substituent, (C1-C30) alkoxy, halogen, (C6-C60) aryl, cyano or (C5-C60) cycloalkyl, or each of R 51 through R 62 may be linked to an adjacent substituent via alkylene or alkenylene to form a (C5-C7)spiro ring or a (C5-C9) fused ring, or may be linked to Ri 7 or Ri 8 via alkylene or alkenylene to form a (C5-C7) fused ring.
  • M 1 is selected from Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag.
  • the compound represented by Chemical Formula 2 may be exemplified the following compounds, but not limited thereto:
  • the electroluminescent device comprises the electroluminescent compound represented by Chemical Formula 1, and may further comprise one or more compound (s) selected from a group consisting of arylamine compounds and styrylarylamine compounds at the same time.
  • the arylamine compound or the styrylarylamine compound may be a compound represented by Chemical Formula 3, but not limited thereto:
  • Ari andAr 2 independently represent hydrogen, deuterium, halogen, (Cl-C ⁇ O)alkyl, (C6-C60) aryl, (C4-C60 ) heteroaryl, (C6-C60) arylamino, (C1-C60) alkylamino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S or (C3-C60) cycloalkyl, and Ari and Ar 2 may be linked via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring;
  • Ar 3 represents (C6-C60) aryl, (C4-C60) heteroaryl or a substituent selected from the following structures, when a is 1:
  • Ar 3 represents (C6-C60) arylene, (C4-C60) heteroarylene or a substituent selected from the following structures, when a is 2:
  • Ar 4 and Ar 5 independently represent (C6-C60 ) arylene or (C4-C60) heteroarylene;
  • R 5 i f R 52 and R 53 independently represent hydrogen, halogen, deuterium, (C1-C60) alkyl or (C6-C60) aryl; b represents an integer from 1 to 4 ; c represents an integer 0 or 1; and the alkyl, aryl, heteroaryl, arylamino, alkylamino, cycloalkyl or heterocycloalkyl of Ari and A ⁇ 2l the aryl, heteroaryl, arylene or heteroarylene of Ar 3 , the arylene or heteroarylene of Ar 4 and Ars, or the alkyl or aryl of R 51 through R 53 may be further substituted by one or more substituent (s) selected from a group consisting of deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C4-C60) heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0
  • the organic layer may further comprise, in addition to the electroluminescent compound represented by Chemical Formula 1, 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 .
  • the organic layer may comprise an electroluminescent layer and a charge generating layer at the same time.
  • An independent electroluminescence type electroluminescent device having a pixel structure in which the electroluminescent device according to the present invention comprising the electroluminescent compound represented by Chemical Formula 1 is used as a subpixel and one or more subpixel (s) comprising one or more metal compound (s) selected from a group consisting of Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au andAg is patterned in parallelmaybe manufactured.
  • the organic layer may further comprise, in addition to the electroluminescent compound, one or more green- or blue-emitting organic compound (s) or organometallic compound (s) to form a white-emitting electroluminescent device.
  • the green- or blue-emitting organic compound or organometallic compound may be exemplified by the compounds represented by Chemical Formulas 4 to 8, but not limited thereto:
  • Arii andAr i2 independently represent (C1-C60) alkyl, (C6-C60) aryl, (C4-C60)heteroaryl, (C6-C60) arylamino, (C1-C60) alkylamino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S or (C3-C60) cycloalkyl, and Ar n and Ari 2 may be linked via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring;
  • Ar i3 represents (C6-C60) aryl, (C4-C60) heteroaryl or a substituent selected from the following structures, when d is 1:
  • Ar i3 represents (C6-C60) arylene, (C4-C60) heteroarylene or a substituent selected from the following structures, when d is 2:
  • Ar i4 and Ar 15 independently represent (C6-C60) arylene or (C4-C60) heteroarylene;
  • R ⁇ i r R ⁇ 2 and R ⁇ j independently represent hydrogen, deuterium, (C1-C60) alkyl or (C6-C60) aryl; e represents an integer from 1 to 4; f represents an integer 0 or 1; the alkyl, aryl, heteroaryl, arylamino, alkylamino, cycloalkyl or heterocycloalkyl of Arn and AiTi 2 , the aryl, heteroaryl, arylene or heteroarylene of Ari 3 , the arylene or heteroarylene of Ari4 and Ar ⁇ 5 , or the alkyl or aryl of R 6 i through R 63 may be further substituted by one or more substituent (s) selected froma group consisting of deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C4-C60) heteroaryl, 5- or
  • R 7 i through R 74 independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C4-C60) heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, (C1-C60) alkylamino, (C6-C60) arylamino, (C6-C60) ar (C1-C60) alkyl, (Cl-C ⁇ O)
  • each of R 7 i through R 74 may be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring; the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylsilyl, alkylsilyl, alkylamino or arylamino of R 7 i through R 74 , or the alicyclic ring or the monocyclic or polycyclic aromatic ring formed as they are linked to an adjacent substituent via (C3-C60) alkylene
  • (C4-C60) heteroaryl 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, O and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl, (C7-C60) bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, (C1-C60) alkylamino, (C6-C60) arylamino, (C6-C60) ar (C1-C60) alkyl, (C1-C60) alkyloxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, (C
  • Lu represents (C6-C60) arylene or (C4-C60) heteroarylene; Li 2 represent anthracenylene;
  • Ar 2I through Rr 2A independently represent hydrogen, deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or (C6-C60) aryl, or the cycloalkyl, aryl or heteroaryl of Ar 2I through Ar 24 may be further substituted by one or more substituent (s) selected from a group consisting of (C6-C60)aryl or (C4-C60) heteroaryl with or without one or more substituent (s) selected from a group consisting of (C1-C60) alkyl with or without halogen substituent, (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl and
  • R 8 i and R 82 independently represent (C6-C60) aryl
  • (C4-C60) heteroaryl 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S or (C3-C60) cycloalkyl, and the aryl or heteroaryl of R 8 i and R 82 may be further substituted by one or more substituent (s) selected from a group consisting of deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxy,
  • R 83 through R 86 independently represent hydrogen, deuterium, (Cl-C ⁇ O)alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or (C6-C60) aryl, and the heteroaryl, cycloalkyl or aryl of R 83 through R 86 may be further substituted by one or more substituent (s) selected from a group consisting of deuterium, (C1-C60) alkyl with or without halogen substituent, (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl and tri (C6-C60) arylsilyl; Gi and G 2 independently represent a chemical bond or (C6-C60)
  • Ar 3 I and Ar 32 represent (C4-C60) heteroaryl or aryl selected from the following structures:
  • the aryl or heteroaryl of Ar 3I and Ar 32 may be substituted by one or more substituent (s) selected from deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60)aryl and (C4-C60) heteroaryl;
  • L 2I represents (C6-C60) arylene, (C4-C60) heteroarylene or a compound having the following structure:
  • the arylene or heteroarylene of L 2 i may be substituted by one or more substituent (s) selected from deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl, (C4-C60) heteroaryl and halogen;
  • R 91A R 92 , R 93 and R 94 independently represent hydrogen, deuterium
  • (C1-C60) alkyl or (C6-C60) aryl, or each of them may be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring; and
  • Rioi f R 102 , R 103 and R 104 independently represent hydrogen, deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl, (C4-C60) heteroaryl or halogen, or each of them may be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring.
  • green- or blue-emitting organic compound or organometallic compound may be exemplified by the following compounds, but not limited thereto:
  • a layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode (s) among the pair of electrodes. More specifically, a chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent layer. A driving stability may be attained therefrom.
  • the chalcogenide may be, for example, SiO x (1 ⁇ x ⁇ 2) , AlO x (1 ⁇ x ⁇ 1.5), SiON, SiAlON, etc.
  • 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.
  • 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 may be placed on the inner surface of one or both electrode (s) among the pair of electrodes.
  • transport of electrons from the mixed region to the electroluminescent layer becomes easier, because the electron transport compound is reduced to an anion.
  • transport of holes from the mixed region to the electroluminescent layer becomes easier, because the hole transport compound is oxidized to a cation.
  • Preferred examples of the oxidative dopant include various Lewis acids and acceptor compounds .
  • Preferred examples of the reductive dopant include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof.
  • FIG. 1 is a cross-sectional view of an OLED device. ⁇ Description of symbols of significant parts of the drawing>
  • Hole injecting layer 4 Hole transport layer
  • Nickel (1.84 g, 2.8 mmol) was added to a 500 mL flask and argon gas was filled therein. After adding ether (50 mL) and Compound E (14.ImL, 42.15 mmol), the mixture was stirred for 30 minutes at room temperature. After adding Compound B (5.0 g, 14.0 mmol) dissolved in ether, the mixture was stirred for 48 hours under reflux. After cooling to room temperature, the mixture was poured to saturated ammonium chloride . After washing with water, followed by extraction with ethyl acetate, Compound F (2.0 g, 69%) was obtained by purification through silica column and drying.
  • Electroluminescent compounds (Compounds 1 to 356) were prepared according to the method of Preparation Examples 1 and 2. Table 1 shows 1 H NMR and MS/FAB data of the prepared electroluminescent compounds. [Table 1]
  • FIG. 1 An OLED device was manufactured using the electroluminescent compound according to the present invention as a host material.
  • FIG 1 shows the cross-sectional view of the OLED device.
  • the ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus.
  • a vacuum deposition apparatus After filling 4,4', 4"-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (2-TNATA) in a cell of the vacuum deposition apparatus, the pressure inside the chamber was reduced to 10 ⁇ 6 torr. Then, 2-TNATA was evaporatedby applying electrical current to the cell .
  • Ahole injection layer 3 having a thickness of 60 nm was formed on the ITO substrate.
  • NPB N 1 N 1 -bis ( ⁇ -naphthyl) -N, N' -diphenyl-4 , 4 '-diamine (NPB) in another cell of the vacuum deposition apparatus, NPB was evaporated by applying electrical current. A hole transport layer 4 having a thickness of 20 nm was formed on the hole injection layer.
  • An electroluminescent layer 5 was formed on the hole transport layer as follows.
  • the compound according to the present invention is
  • an electroluminescent dopant e.g., (piq) 2 lr(acac)
  • the two materials were evaporated at different speed, so that an electroluminescent layer 5 having a thickness of 30 nm was formed on the hole transport layer at 4 to 10 mol%.
  • the electroluminescent compounds according to the present invention exhibited superior electroluminescence characteristics as compared to the existing material.
  • Example 3 1) . Especially, the device of Example 3 was operated at a voltage
  • Example 8 exhibited a driving voltage of 4.5 V and a power efficiency of 6.3 lm/W at 1000 cd/m 2 .
  • the device using the electroluminescent compound according to the present invention as host material has excellent electroluminescence characteristics and power consumption can be improved by increasing power efficiency by 1.9-3.9 lm/W through decreased driving voltage.
  • the electroluminescent compound according to the present invention When used for a host material of an electroluminescent material in an OLED device, the electroluminescent compound according to the present invention provides better red luminous efficiency as compared to existing host materials and excellent life property of the material . Therefore, it can be used tomanufacture OLEDs having very good operation life.

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Abstract

Provided are an electroluminescent compound and an electroluminescent device comprising the same as a host material: When used as a host material of an electroluminescent material in an OLED device, the disclosed electroluminescent compound exhibits superior red luminous efficiency and excellent life property of the material, as compared to the existing host material. Therefore, it can be used to manufacture OLEDs having very superior operation life.

Description

[DESCRIPTION]
[invention Title]
NOVEL ORGANOMETALLIC COMPOUNDS FOR ELECTROLUMINESCENCE AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME [Technical Field]
The present invention relates to an electroluminescent compound comprising a metal complex exhibiting excellent electrical conductivity and high luminous efficiency, and an electroluminescent device comprising the same as a host material. [Background Art]
The most important factor that determines luminous efficiency of an OLED is the electroluminescent material . Atpresent, fluorescent materials are widely used for the electroluminescent material. But, phosphorescent materials are better when considering the electroluminescence mechanism. Theoretically, phosphorescent materials can improve the luminous efficiency by 4-fold.
Until now, iridium(III) complex-based phosphorescent materials are widely known. Such materials as (acac) Ir (btp) 2, Ir(ppy)3 and Firpic are known for red, green andblue colors, respectively. Recently, a lot of researches on phosphorescent materials are underway, especially in Japan, Europe and the US.
Figure imgf000003_0001
(acac)lr(btp)2 Ir(PPYh Firpic
At present, CBP is the most widely known as a host material for a phosphorescent material. High-efficiency OLEDs using a hole blocking layer comprising BCP, BAIg, etc. are reported. High-performance OLEDs using BAIq derivatives as a host were reported by Pioneer (Japan) and others.
Figure imgf000004_0001
CBP BBCCPP BBAAIIqq BAIq derivative
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 (π / 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 suchasBAlq, 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. Further, the OLED devices do not have satisfactory operation life. Therefore, development of more stable, higher-performance host materials is required.
With regard thereto, many studies have been carried out since mid-1990s, including complexes for blue electroluminescent materials . However, they are simply used for the electroluminescent material, and little is known about application as a host material.
[Disclosure] [Technical Problem]
In order to solve the aforesaidproblems, in an aspect, the present invention provides an electroluminescent compound having a novel ligand metal complex with very superior electroluminescence characteristics and physical properties as compared to existing organic host materials as a backbone. In another aspect, the present invention provides an electroluminescent device comprising the electroluminescent compound as a host material. In another aspect, the present invention provides an organic solar cell comprising the electroluminescent compound.
[Technical Solution]
Exemplary embodiments now will be described more fully hereinafter with reference to the accompanying drawings, in which exemplary embodiments are shown. This disclosure may, however, be embodied in many different forms and should not be construed as limited to the exemplary embodiments set forth therein. Rather, these exemplary embodiments are provided so that this disclosure will be thorough and complete, andwill fully convey the scope of this disclosure to those skilled in the art . In the description, details of well-known features and techniques may be omitted to avoid unnecessarily obscuring the presented embodiments.
The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of this disclosure. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. Furthermore, the use of the terms a, an, etc. does not denote a limitation of quantity, but rather denotes the presence of at least one of the referenced item. The use of the terms "first", "second", and the like does not imply any particular order, but they are included to identify individual elements . Moreover, the use of the terms first, second, etc. does not denote any order or importance, but rather the terms first, second, etc. are used to distinguish one element from another. It will be further understood that the terms "comprises" and/or "comprising", or "includes" and/or "including" when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.
Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.
The shape, size and regions, and the like, of the drawing may be exaggerated for clarity.
The present invention relates to an electroluminescent compound represented by Chemical Formula 1 and an electroluminescent device comprising the same as a host material:
Figure imgf000007_0001
wherein M represents a divalent or trivalent metal; n represents the cationic valence of M;
Ri through R8 independently represent hydrogen, (C1-C60) alkyl, halogen, cyano, (C3-C60) cycloalkyl, 5- or 6-memberedheterocycloalkyl containing one or more heteroatom (s) selected from N, O and S, (C7-C60)bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl,
(C6-C60)aryl, (C1-C60) alkoxy, (C1-C60) alkylthio, (C6-C60 ) aryloxy,
(C3-C60 ) heteroaryl containing one or more heteroatom ( s ) selected from
N, 0 and S, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl,
(C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, di (C6-C60) arylboranyl, di (C1-C60) alkylboranyl, carboxyl, nitro or hydroxyl; and the alkyl, cycloalkyl, heterocycloalkyl, bicycloalkyl, adamantyl, alkenyl, alkynyl, aryl, alkoxy, alkylthio, aryloxy, heteroaryl, arylthio, alkoxycarbonyl, alkylcarbonyl, arylcarbonyl, alkylamino, arylamino, trialkylsilyl, dialkylarylsilyl, triarylsilyl, diarylboranyl or dialkylboranyl of Ri through R& may be further substituted by one or more substituent (s) selected from a group consisting of (C1-C60) alkyl, halogen, cyano,
(C3-C60) cycloalkyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, O and S, (C7-C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl,
(Cl-CβO)alkoxy, (C1-C60) alkylthio, (C6-C60) aryloxy,
(C3-C60) heteroaryl containing one or more heteroatom (s) selected from
N, O and S, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, carboxyl, nitro and hydroxyl, except for the case where all of Ri through Rg are hydrogens. In the present invention, "alkyl", "alkoxy" and other substituents including "alkyl" moietymay be either linear or branched.
In the present invention, "aryl" means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but 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 all of 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 N, 0, S and Si as aromatic ring backbone atom(s), other remaining aromatic ring backbone atoms being carbon. It may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with a benzene ring, and may be partially saturated. The heteroaryl includes a divalent aryl group wherein the heteroatom (s) in the ring may be oxidized or quaternized to form, for example, N-oxide or quaternary salt . Specific examples include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, benzodioxolyl, etc., N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide, etc.), quaternary salt thereof, etc., but not limited thereto.
And, in the present invention, the substituents including " (C1-C60) alkyl" moiety may have 1 to 60 carbon atoms, 1 to 20 carbon atoms, or 1 to 10 carbon atoms. The substituents including " (C6-C60) aryl" moiety may have 6 to 60 carbon atoms, 6 to 20 carbon atoms, or 6 to 12 carbon atoms. The substituents including " (C3-C60) heteroaryl" moiety may have 3 to 60 carbon atoms, 4 to 20 carbon atoms, or 4 to 12 carbon atoms. The substituents including
" (C3-C60) cycloalkyl" moiety may have 3 to 60 carbon atoms, 3 to 20 carbon atoms, or 3 to 7 carbon atoms. The substituents including " (C2-C60) alkenyl or alkynyl" moiety may have 2 to 60 carbon atoms, 2 to 20 carbon atoms, or 2 to 10 carbon atoms.
Specifically, Ri through R8 may independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, trifluoromethyl, perfluoroethyl, perfluorobutyl, chloro, fluoro, cyano, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, pyridyl, furyl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, carbazolyl, phenanthridinyl, quinolyl, isoquinolyl, adamantyl, ethenyl, methylethenyl, phenylethenyl, ethynyl, methylethynyl, phenylethynyl, phenyl, biphenyl, naphthyl, 9, 9-dimethylfluorenyl, 9, 9-diphenylfluorenyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, hexyloxy, methylthio, phenyloxy, phenylthio, methoxycarbonyl, butoxycarbonyl, methylcarbonyl, ethylcarbonyl, butylcarbonyl, phenylcarbonyl, naphthylcarbonyl, dimethylamino, diethylamino, diphenylamino, trimethylsilyl, triphenylsilyl, t-butyldimethylsilyl, diphenylboranyl, dimethylboranyl, carboxyl, nitro or hydroxyl; and The pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, pyridyl, furyl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, carbazolyl, phenanthridinyl, quinolyl, isoquinolyl, phenyl, biphenyl, naphthyl, fluorenyl, diphenylboranyl or dimethylboranyl of Ri through Rg may be further substituted by one or more substituent (s) selected from a group consisting of methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, trifluoromethyl, perfluoroethyl, perfluorobutyl, chloro, fluoro, cyano, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, pyridyl, furyl, thienyl, pyrrolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, carbazolyl, phenanthridinyl, quinolyl, isoquinolyl, adamantyl, ethenyl, methylethenyl, phenylethenyl, ethynyl, methylethynyl, phenylethynyl, phenyl, biphenyl, naphthyl, 9, 9-dimethylfluorenyl, 9, 9-diphenylfluorenyl, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, t-butoxy, hexyloxy, methylthio, phenyloxy, phenylthio, methoxycarbonyl, butoxycarbonyl, methylcarbonyl, ethylcarbonyl, butylcarbonyl, phenylcarbonyl, naphthylcarbonyl, dimethylamino, diethylamino, diphenylamino, trimethylsilyl, triphenylsilyl, t-butyldimethylsilyl, carboxyl, nitro and hydroxyl . In Chemical Formula 1, M represents a divalent metal selected from a group consisting of Be, Zn, Mg, Ca, Cu and Ni, or a trivalent metal selected from a group consisting of Al, In, Co, Ga and B.
More specifically, the electroluminescent compound represented by Chemical Formula 1 may be exemplified by following compounds, but not limited thereto:
Figure imgf000012_0001
Figure imgf000012_0002
Figure imgf000012_0003
Figure imgf000013_0001
Figure imgf000013_0002
13 14 15
Figure imgf000013_0003
16 17 18
Figure imgf000013_0004
11 19 20 21
Figure imgf000014_0001
22 23 24
Figure imgf000014_0002
25 26
Figure imgf000014_0003
27 28
Figure imgf000014_0004
29 30
Figure imgf000015_0001
31 32
Figure imgf000015_0002
33 34
Figure imgf000015_0003
35 36 37
Figure imgf000015_0004
38 39
Figure imgf000016_0001
40 41
Figure imgf000016_0002
42 43
Figure imgf000016_0003
44 45
Figure imgf000016_0004
46 47
Figure imgf000017_0001
48 49
Figure imgf000017_0002
50 51
Figure imgf000017_0003
52 53
Figure imgf000017_0004
54 55
Figure imgf000018_0001
56 57
Figure imgf000018_0002
58 59
Figure imgf000018_0003
60 61 62
Figure imgf000019_0001
65 66
Figure imgf000019_0002
67 68
Figure imgf000019_0003
69 70 71
Figure imgf000020_0001
72 73 74
Figure imgf000020_0002
75 76 77
Figure imgf000020_0003
78 79 80
Figure imgf000020_0004
82 83
Figure imgf000020_0005
84 85 86
Figure imgf000021_0001
87 88
Figure imgf000021_0002
89 90 91
Figure imgf000021_0003
92 93 94
Figure imgf000021_0004
95 96
Figure imgf000021_0005
97 98
Figure imgf000022_0001
99 100
Figure imgf000022_0002
101 102 103
Figure imgf000022_0003
104 105
Figure imgf000022_0004
106 107
Figure imgf000022_0005
108 109
Figure imgf000023_0001
110 111
Figure imgf000023_0002
112 113
Figure imgf000023_0003
114 115
Figure imgf000023_0004
116 117
Figure imgf000023_0005
118 119
Figure imgf000024_0001
120 121 122
Figure imgf000024_0002
123 124
Figure imgf000024_0003
125 126
Figure imgf000024_0004
127 128
Figure imgf000024_0005
129 130 131
Figure imgf000025_0001
132 133
Figure imgf000025_0002
134 135
Figure imgf000025_0003
136 137
Figure imgf000025_0004
138 139
Figure imgf000026_0001
140 141
Figure imgf000026_0002
142 143 144
Figure imgf000026_0003
145 146
Figure imgf000026_0004
147 148
Figure imgf000027_0001
149 150 151
Figure imgf000027_0002
152 153
Figure imgf000027_0003
154 155
Figure imgf000027_0004
156 157
Figure imgf000028_0001
158 159
Figure imgf000028_0002
160 161
Figure imgf000028_0003
162 163 164
Figure imgf000028_0004
165 166
Figure imgf000029_0001
167 168
Figure imgf000029_0002
169 170
Figure imgf000029_0003
171 172
Figure imgf000029_0004
173 174
Figure imgf000030_0001
175 176
Figure imgf000030_0002
177 178
Figure imgf000030_0003
179 180
Figure imgf000030_0004
181 182
Figure imgf000031_0001
183 184
Figure imgf000031_0002
185 186
Figure imgf000031_0003
187 188
Figure imgf000031_0004
189 190
Figure imgf000032_0001
191 192
Figure imgf000032_0002
193 194
Figure imgf000032_0003
195 196 197
Figure imgf000032_0004
198 199
Figure imgf000033_0001
200 201
Figure imgf000033_0002
202 203
Figure imgf000033_0003
204 205 206
Figure imgf000033_0004
207 208
Figure imgf000034_0001
209 210
Figure imgf000034_0002
211 212 213
Figure imgf000034_0003
214 215
Figure imgf000034_0004
216 217
Figure imgf000034_0005
218 219
Figure imgf000035_0001
220 221 222
Figure imgf000035_0002
223 224 225
Figure imgf000035_0003
226 227 228
Figure imgf000035_0004
229 230 231
Figure imgf000036_0001
232 233 234
Figure imgf000036_0002
235 236 237
Figure imgf000036_0003
Figure imgf000036_0004
238 239 240
Figure imgf000036_0005
241 242
Figure imgf000037_0001
243 244 245
Figure imgf000037_0002
246 247 248
Figure imgf000037_0003
249 250 251
Figure imgf000038_0001
252 253 254
Figure imgf000038_0002
255 256 257
Figure imgf000038_0003
8 259 260
Figure imgf000038_0004
261 262 263 264
Figure imgf000039_0001
265 266 267 268 269
Figure imgf000039_0002
270 271 272 273
Figure imgf000039_0003
274 275 276 277
Figure imgf000039_0004
278 279 280 281 282
Figure imgf000039_0005
283 284 285 286 287
Figure imgf000040_0001
288 289 290 291 292
Figure imgf000040_0002
293 294 295 296
Figure imgf000040_0003
297 298 299 300
Figure imgf000040_0004
301 302 303 304
Figure imgf000041_0001
305 306 307 308
Figure imgf000041_0002
309 310 311 312 313
Figure imgf000041_0003
314 315 316 317 318
Figure imgf000041_0004
319 320 321 322
Figure imgf000042_0001
323 324 325 326 327
Figure imgf000042_0002
328 329 330 331 332
Figure imgf000042_0003
333 334 335 336 337
Figure imgf000042_0004
338 339 340 341 342
Figure imgf000042_0005
343 344 345 346
Figure imgf000043_0001
347 348 349 350
Figure imgf000043_0002
351 352 353 354
Figure imgf000043_0003
355 356
The present invention further provides an organic solar cell. The organic solar cell according to the present invention comprises one or more electroluminescent compound (s) represented by Chemical Formula 1.
The present invention further provides an electroluminescent device. The electroluminescent device according to the present invention 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 electroluminescent compound (s) represented by Chemical Formula 1. In the electroluminescent device according to the present invention, the organic layer further comprises an electroluminescent layer. The electroluminescent layer comprises one or more electroluminescent compound (s) represented by Chemical Formula 1, as an electroluminescent host, and one or more electroluminescent dopant (s) . The electroluminescent dopant used in the electroluminescent device according to the present invention is not particularly limited, but may be exemplified by the compounds 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; ligands L101, L102 and L103 are independently selected from the following structures:
Figure imgf000044_0001
Figure imgf000045_0001
wherein
Rn through R13 independently represent hydrogen, (C1-C60) alkyl with or without halogen substituent, (C6-C60)aryl with or without (C1-C60) alkyl substituent or halogen;
Ri4 through R29 independently represent hydrogen, (C1-C60 ) alkyl, (Cl-C30)alkoxy, (C3-C60) cycloalkyl, (C2-C30) alkenyl, (C6-C60) aryl, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino, SF5, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, cyano or halogen, and the alkyl, cycloalkyl, alkenyl or aryl of Ri4 through R29 may be further substituted by one or more substituent (s) selected from (C1-C60) alkyl, (C6-C60) aryl and halogen;
R30 through R33 independently represent hydrogen, (C1-C60) alkyl with or without halogen substituent or (C6-C60)aryl with or without (C1-C60) alkyl substituent; R34 and R35 independently represent hydrogen, (C1-C60) alkyl, (C6-C60) aryl or halogen, OrR34 and R35 may be linked via (C3-C12) alkylene or (C3-C12) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring, and the alkyl or aryl of R34 and R35, or the alicyclic ring or the monocyclic or polycyclic aromatic ring formed as they are linked via (C3-C12) alkylene or
(C3-C12) alkenylene with or without a fused ring may be further substituted by one or more substituent (s) selected from (C1-C60) alkyl with or without halogen substituent, (C1-C30) alkoxy, halogen, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl and (C6-C60) aryl; R36 represents (C1-C60) alkyl, (C6-C60) aryl, (C5-C60) heteroaryl containing one or more heteroatom (s) selected from N, 0 and S or halogen;
R37 through R39 independently represent hydrogen, (C1-C60) alkyl,
(Cβ-CβO)aryl or halogen, and the alkyl or aryl of R36 through R39 may be further substituted halogen or (C1-C60) alkyl; R40 and R41 independently represent hydrogen, (C1-C20) alkyl with or without halogen substituent, (C6-C20) aryl, halogen, cyano, tri (C1-C20) alkylsilyl, di (C1-C20) alkyl (C6-C20) arylsilyl, tri (C6-C20)arylsilyl, (C1-C20) alkoxy, (C1-C20) alkylcarbonyl, (C6-C20) arylcarbonyl, di (C1-C20) alkylamino or di (C6-C20) arylamino, or R40 and R4I may be linked via (C3-C12 ) alkylene or (C3-C12) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring; the alkyl or aryl of R40 and R4i, or the alicyclic ring or the monocyclic or polycyclic aromatic ring formed as they are linked via
(C3-C12) alkylene or (C3-C12) alkenylene with or without a fused ring may be further substituted by one or more substituent (s) selected from (C1-C20) alkyl with or without halogen substituent, halogen, cyano, tri (C1-C20) alkylsilyl, di (C1-C20) alkyl (C6-C20) arylsilyl, tri (C6-C20) arylsilyl, (C1-C20) alkoxy, (C1-C20) alkylcarbonyl, (C6-C20) arylcarbonyl, di (C1-C20) alkylamino, di (C6-C20) arylamino, phenyl, naphthyl, anthryl, fluorenyl and spirobifluorenyl, or may be further substituted by phenyl or fluorenyl with one or more substituent (s) selected from a group consisting of (C1-C20) alkyl with or without halogen substituent , halogen, cyano, tri (C1-C20) alkylsilyl, di (C1-C20) alkyl (C6-C20) arylsilyl, tri (C6-C20) arylsilyl, (C1-C20) alkoxy, (C1-C20) alkylcarbonyl, (C6-C20) arylcarbonyl, di (C1-C20) alkylamino, di (C6-C20) arylamino, phenyl, naphthyl, anthryl, fluorenyl and spirobifluorenyl;
R42 through R49 independently represent hydrogen, (C1-C20) alkyl with or without halogen substituent, (C1-C20) alkoxy, (C3-C12) cycloalkyl, halogen, cyano, (C6-C20) aryl, (C4-C20) heteroaryl, tri (C1-C20) alkylsilyl, di (Cl-C20)alkyl (C6-C20) arylsilyl or tri (C6-C20) arylsilyl; and
Q represents V V
Figure imgf000048_0001
or wherein R5i through R62fe independently represent hydrogen, (C1-C60) alkyl with or without halogen substituent, (C1-C30) alkoxy, halogen, (C6-C60) aryl, cyano or (C5-C60) cycloalkyl, or each of R51 through R62 may be linked to an adjacent substituent via alkylene or alkenylene to form a (C5-C7)spiro ring or a (C5-C9) fused ring, or may be linked to Ri7 or Ri8 via alkylene or alkenylene to form a (C5-C7) fused ring.
M1 is selected from Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag. Specifically, the compound represented by Chemical Formula 2 may be exemplified the following compounds, but not limited thereto:
Figure imgf000048_0002
Figure imgf000048_0004
Figure imgf000048_0003
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000053_0001
The electroluminescent device according to the present invention comprises the electroluminescent compound represented by Chemical Formula 1, and may further comprise one or more compound (s) selected from a group consisting of arylamine compounds and styrylarylamine compounds at the same time. For example, the arylamine compound or the styrylarylamine compound may be a compound represented by Chemical Formula 3, but not limited thereto:
Figure imgf000054_0001
wherein
Ari andAr2 independently represent hydrogen, deuterium, halogen, (Cl-CβO)alkyl, (C6-C60) aryl, (C4-C60 ) heteroaryl, (C6-C60) arylamino, (C1-C60) alkylamino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S or (C3-C60) cycloalkyl, and Ari and Ar2 may be linked via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring;
Ar3represents (C6-C60) aryl, (C4-C60) heteroaryl or a substituent selected from the following structures, when a is 1:
Figure imgf000054_0002
Ar3 represents (C6-C60) arylene, (C4-C60) heteroarylene or a substituent selected from the following structures, when a is 2:
Figure imgf000054_0003
Ar4 and Ar5 independently represent (C6-C60 ) arylene or (C4-C60) heteroarylene;
R 5if R52 and R53 independently represent hydrogen, halogen, deuterium, (C1-C60) alkyl or (C6-C60) aryl; b represents an integer from 1 to 4 ; c represents an integer 0 or 1; and the alkyl, aryl, heteroaryl, arylamino, alkylamino, cycloalkyl or heterocycloalkyl of Ari and Aτ2l the aryl, heteroaryl, arylene or heteroarylene of Ar3, the arylene or heteroarylene of Ar4 and Ars, or the alkyl or aryl of R51 through R53 may be further substituted by one or more substituent (s) selected from a group consisting of deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C4-C60) heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom(s) selected from N, 0 and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, (C1-C60) alkylamino, (Cβ-CβO) arylamino, (C6-C60) ar (C1-C60) alkyl, (C6-C60)aryloxy, (C1-C60) alkyloxy, (C6-C60) arylthio, (C1-C60) alkylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro and hydroxyl . More specifically, the arylamine compound or the styrylarylamine compound may be exemplified by the following compounds, but not limited thereto:
Figure imgf000056_0001
In the electroluminescent device according to the present invention, the organic layer may further comprise, in addition to the electroluminescent compound represented by Chemical Formula 1, 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 . Also, the organic layer may comprise an electroluminescent layer and a charge generating layer at the same time.
An independent electroluminescence type electroluminescent device having a pixel structure in which the electroluminescent device according to the present invention comprising the electroluminescent compound represented by Chemical Formula 1 is used as a subpixel and one or more subpixel (s) comprising one or more metal compound (s) selected from a group consisting of Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au andAg is patterned in parallelmaybe manufactured.
The organic layer may further comprise, in addition to the electroluminescent compound, one or more green- or blue-emitting organic compound (s) or organometallic compound (s) to form a white-emitting electroluminescent device. The green- or blue-emitting organic compound or organometallic compound may be exemplified by the compounds represented by Chemical Formulas 4 to 8, but not limited thereto:
Figure imgf000057_0001
Figure imgf000058_0001
wherein
Arii andAri2 independently represent (C1-C60) alkyl, (C6-C60) aryl, (C4-C60)heteroaryl, (C6-C60) arylamino, (C1-C60) alkylamino, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S or (C3-C60) cycloalkyl, and Arn and Ari2 may be linked via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring;
Ari3 represents (C6-C60) aryl, (C4-C60) heteroaryl or a substituent selected from the following structures, when d is 1:
Figure imgf000058_0002
Ari3 represents (C6-C60) arylene, (C4-C60) heteroarylene or a substituent selected from the following structures, when d is 2:
Figure imgf000058_0003
Ari4 and Ar15 independently represent (C6-C60) arylene or (C4-C60) heteroarylene;
Rδir Rβ2 and Rζj independently represent hydrogen, deuterium, (C1-C60) alkyl or (C6-C60) aryl; e represents an integer from 1 to 4; f represents an integer 0 or 1; the alkyl, aryl, heteroaryl, arylamino, alkylamino, cycloalkyl or heterocycloalkyl of Arn and AiTi2, the aryl, heteroaryl, arylene or heteroarylene of Ari3, the arylene or heteroarylene of Ari4 and Arχ5, or the alkyl or aryl of R6i through R63 may be further substituted by one or more substituent (s) selected froma group consisting of deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C4-C60) heteroaryl, 5- or
6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano,
(C1-C60) alkylamino, (C6-C60) arylamino, (C6-C60) ar (C1-C60) alkyl,
(Cβ-CβO)aryloxy, (C1-C60) alkyloxy, (C6-C60) arylthio,
(C1-C60) alkylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl,
(C6-C60) arylcarbonyl, carboxyl, nitro and hydroxyl;
Figure imgf000059_0001
wherein
R7i through R74 independently represent hydrogen, deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl, (C4-C60) heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl, (C7-C60)bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, (C1-C60) alkylamino, (C6-C60) arylamino, (C6-C60) ar (C1-C60) alkyl, (Cl-CβO)alkyloxy, (C1-C60) alkylthio, (C6-C60) aryloxy,
(C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, carboxyl, nitro or hydroxyl, or each of R7i through R74 may be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring; the alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, heteroaryl, arylsilyl, alkylsilyl, alkylamino or arylamino of R7i through R74, or the alicyclic ring or the monocyclic or polycyclic aromatic ring formed as they are linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring may be further substituted by one or more substituent (s) selected from deuterium, halogen, (C1-C60) alkyl, (C6-C60) aryl,
(C4-C60) heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, O and S, (C3-C60) cycloalkyl, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl, tri (C6-C60) arylsilyl, adamantyl, (C7-C60) bicycloalkyl, (C2-C60) alkenyl, (C2-C60) alkynyl, cyano, (C1-C60) alkylamino, (C6-C60) arylamino, (C6-C60) ar (C1-C60) alkyl, (C1-C60) alkyloxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl,
(C6-C60) arylcarbonyl, carboxyl, nitro and hydroxyl;
(Ar21) 9-L11-(Ar22J11 (7)
(Ar2S)1-L12-(Ar24J3 (8) wherein
Lu represents (C6-C60) arylene or (C4-C60) heteroarylene; Li2 represent anthracenylene;
Ar2I through Rr2A independently represent hydrogen, deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or (C6-C60) aryl, or the cycloalkyl, aryl or heteroaryl of Ar2I through Ar24 may be further substituted by one or more substituent (s) selected from a group consisting of (C6-C60)aryl or (C4-C60) heteroaryl with or without one or more substituent (s) selected from a group consisting of (C1-C60) alkyl with or without halogen substituent, (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl and tri (C6-C60) arylsilyl, deuterium, (C1-C60) alkyl with or without halogen substituent, (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl and tri (C6-C60) arylsilyl; and g, h, i and j independently represent an integer from 0 to 4. The compound represented by Chemical Formula 7 or 8 may be exemplified by anthracene derivatives or benz [a] anthracene derivatives represented by Chemical Formulas 9 to 11:
Figure imgf000061_0001
Figure imgf000062_0001
wherein
R8i and R82 independently represent (C6-C60) aryl,
(C4-C60) heteroaryl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S or (C3-C60) cycloalkyl, and the aryl or heteroaryl of R8i and R82 may be further substituted by one or more substituent (s) selected from a group consisting of deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxy,
(C3-C60) cycloalkyl, (C6-C60) aryl, (C4-C60) heteroaryl, halogen, cyano, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl and tri (C6-C60) arylsilyl;
R83 through R86 independently represent hydrogen, deuterium, (Cl-CβO)alkyl, (C1-C60) alkoxy, halogen, (C4-C60) heteroaryl, (C5-C60) cycloalkyl or (C6-C60) aryl, and the heteroaryl, cycloalkyl or aryl of R83 through R86 may be further substituted by one or more substituent (s) selected from a group consisting of deuterium, (C1-C60) alkyl with or without halogen substituent, (C1-C60) alkoxy, (C3-C60) cycloalkyl, halogen, cyano, tri (C1-C60) alkylsilyl, di (C1-C60) alkyl (C6-C60) arylsilyl and tri (C6-C60) arylsilyl; Gi and G2 independently represent a chemical bond or (C6-C60) arylene with or without one or more substituent (s) selected from (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl, (C4-C60) heteroaryl and halogen;
Ar3I and Ar32 represent (C4-C60) heteroaryl or aryl selected from the following structures:
Figure imgf000063_0001
the aryl or heteroaryl of Ar3I and Ar32 may be substituted by one or more substituent (s) selected from deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60)aryl and (C4-C60) heteroaryl;
L2I represents (C6-C60) arylene, (C4-C60) heteroarylene or a compound having the following structure:
Figure imgf000063_0002
the arylene or heteroarylene of L2i may be substituted by one or more substituent (s) selected from deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl, (C4-C60) heteroaryl and halogen;
R91A R92, R93 and R94 independently represent hydrogen, deuterium,
(C1-C60) alkyl or (C6-C60) aryl, or each of them may be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring; and
Rioif R102, R103 and R104 independently represent hydrogen, deuterium, (C1-C60) alkyl, (C1-C60) alkoxy, (C6-C60) aryl, (C4-C60) heteroaryl or halogen, or each of them may be linked to an adjacent substituent via (C3-C60) alkylene or (C3-C60) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring.
More specifically, the green- or blue-emitting organic compound or organometallic compound may be exemplified by the following compounds, but not limited thereto:
Figure imgf000064_0001
Figure imgf000065_0001
63
Figure imgf000066_0001
Figure imgf000066_0002
Figure imgf000066_0004
Figure imgf000066_0005
Figure imgf000066_0006
Figure imgf000066_0003
64
Figure imgf000067_0001
65
Figure imgf000068_0001
66
Figure imgf000069_0001

Figure imgf000070_0001

Figure imgf000071_0001

Figure imgf000072_0001
In the electroluminescent device according to the present invention, a layer (hereinafter referred to as "surface layer") selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode (s) among the pair of electrodes. More specifically, a chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent layer. A driving 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.
Further, in the electroluminescent device according to the present invention, 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 may be placed on the inner surface of one or both electrode (s) among the pair of electrodes. In that case, transport of electrons from the mixed region to the electroluminescent layer becomes easier, because the electron transport compound is reduced to an anion. Further, transport of holes from the mixed region to the electroluminescent layer becomes easier, because the hole transport compound is oxidized to a cation. Preferred examples of the oxidative dopant include various Lewis acids and acceptor compounds .
Preferred examples of the reductive dopant include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof.
[Description of Drawings]
The above and other aspects, features and advantages of the present invention will become apparent from the following description of preferred embodiments given in conjunction with the accompanying drawing, in which:
FIG. 1 is a cross-sectional view of an OLED device. <Description of symbols of significant parts of the drawing>
1: Glass
2 : Transparent electrode
3: Hole injecting layer 4 : Hole transport layer
5: Electroluminescent layer
6: Electron transport layer
7: Electron injecting layer
8: Al cathode [Best Mode]
Hereinafter, the novel electroluminescent compounds according to the present invention, preparation method thereof, and electroluminescence characteristics of the devices will be described for the understanding of the present invention. However, the following examples are for illustrative purposes only and not intended to limit the scope of the present invention.
[Preparation Example 1] Preparation of Compound 191
Figure imgf000075_0001
Preparation of Compound B
Chloroform (1 L) and acetic acid (205 mL) were added to a 5 L round-bottom flask containing Compound A (10 g, 51.2 mmol) . After slowly adding iodine (11.7 g, 46.1 mmol) dissolved in methanol (1
L) , the mixture was stirred for 6 hours at 70 °C. The reaction mixture was cooled to room temperature and then neutralized. After washing with water and sodium thiosulfate, followed by extraction with methylene chloride, CompoundB (9.7 g, 59%) was obtainedby purification through silica column and drying.
Preparation of Compound C
Compound C (4.2 g, 34.4 mmol) and tetrakis (triphenylphosphine) palladium (994 mg, 0.86 mmol) were added to a 500 mL flask containing Compound B (9.2 g, 28.7 mmol) , and argon gas was filled therein. After adding toluene (100 mL) , ethanol (50 mL) and 2 M potassium carbonate (50 mL) , reflux was performed for 2 hours. After cooling to room temperature and washing with water, followed by extraction with ethyl acetate, Compound D (2.7 g, 35%) was obtained by purification through silica column and drying. Preparation of Compound 191
Sodium hydroxide (398 mg, 9.95 mmol) and methanol (18OmL) were added to a 500 mL flask containing Compound D (2.7 g, 9.95 mmol) and the mixture was stirred. After adding beryllium sulfate tetrahydrate (980 mg, 5.53 mmol), mixture was stirred for 12 hours. The produced solid was filtered, washed with water and ethanol and then dried. Compound 191 (2.7 g, 99%) was obtained.
[Preparation Example 2] Preparation of Compound 191
Figure imgf000076_0001
Preparation of Compound F
Nickel (1.84 g, 2.8 mmol) was added to a 500 mL flask and argon gas was filled therein. After adding ether (50 mL) and Compound E (14.ImL, 42.15 mmol), the mixture was stirred for 30 minutes at room temperature. After adding Compound B (5.0 g, 14.0 mmol) dissolved in ether, the mixture was stirred for 48 hours under reflux. After cooling to room temperature, the mixture was poured to saturated ammonium chloride . After washing with water, followed by extraction with ethyl acetate, Compound F (2.0 g, 69%) was obtained by purification through silica column and drying. Preparation of Compound 24 Sodium hydroxide (384 mg, 9.6 mmol) and methanol (180 mL) were added to a 500 mL flask containing Compound F (2.0 g, 9.6 mmol) and the mixture was stirred. Zinc acetate (1.2 g, 5.33 mmol) was added thereto and stirring was carried out for 12 hours. The produced solid was filtered, washed with water and ethanol and then dried. Compound 24 (2.0 g, 86%) was obtained.
Electroluminescent compounds (Compounds 1 to 356) were prepared according to the method of Preparation Examples 1 and 2. Table 1 shows 1H NMR and MS/FAB data of the prepared electroluminescent compounds. [Table 1]
Figure imgf000077_0001
Figure imgf000078_0001
Figure imgf000079_0001
Figure imgf000080_0001
[Examples 1-9] Manufacture of OLED device using the electroluminescent compound according to the present invention
An OLED device was manufactured using the electroluminescent compound according to the present invention as a host material. FIG.
1 shows the cross-sectional view of the OLED device.
First, a transparent electrode ITO film (15Ω/D, Samsung Corning)
2 prepared from a glass substrate for an OLED 1 was subjected to ultrasonic washing sequentially using trichloroethylene, acetone, ethanol and distilled water, and stored in isopropanol for later use.
Next, the ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus. After filling 4,4', 4"-tris (N, N- (2-naphthyl) -phenylamino) triphenylamine (2-TNATA) in a cell of the vacuum deposition apparatus, the pressure inside the chamber was reduced to 10~6 torr. Then, 2-TNATA was evaporatedby applying electrical current to the cell . Ahole injection layer 3 having a thickness of 60 nm was formed on the ITO substrate.
Figure imgf000081_0001
2-TNATA
Subsequently, after filling
N1 N1 -bis (α-naphthyl) -N, N' -diphenyl-4 , 4 '-diamine (NPB) in another cell of the vacuum deposition apparatus, NPB was evaporated by applying electrical current. A hole transport layer 4 having a thickness of 20 nm was formed on the hole injection layer.
Figure imgf000081_0002
NPB
An electroluminescent layer 5 was formed on the hole transport layer as follows. The compound according to the present invention
(e.g., Compound 1) vacuum sublimed at 10~6 torr was filled in a cell of a vacuum deposition apparatus as a host material, and an electroluminescent dopant (e.g., (piq)2lr(acac)) was filled in another cell. The two materials were evaporated at different speed, so that an electroluminescent layer 5 having a thickness of 30 nm was formed on the hole transport layer at 4 to 10 mol%.
Figure imgf000082_0001
Compound 1
Thereafter, tris (8-hydroxyquinoline) -aluminum (III) (AIq) was deposited with a thickness of 20 nm as an electron transport layer 6. Then, lithium quinolate (Liq) was deposited with a thickness of 1 to 2 nm as an electron injection layer 7. Then, an Al cathode 8 having a thickness of 150 nm was formed using another vacuum deposition apparatus to manufacture an OLED.
Figure imgf000082_0002
AIq Liq Each OLED electroluminescent material was purified by vacuum sublimation at 10~6 torr.
[Comparative Example 1] Manufacture of OLED device using existing electroluminescent material An OLED device was manufactured as in Example 1, except that bis (2-methyl-8-quinolinato) (p-phenylphenolato) aluminum (III) (BAIq) was used as an electroluminescent host material instead of the electroluminescent compound according to the present invention.
Figure imgf000083_0001
BAIq
[TestExample 1] Confirmation of characteristics ofmanufactured OLED device
Driving voltage and power efficiency of the OLED devices manufactured in Examples 1-9 and Comparative Example 1 were measured at 1,000 cd/m2. The result is given in Table 2.
As seen in Table 2, the electroluminescent compounds according to the present invention exhibited superior electroluminescence characteristics as compared to the existing material.
[Table 2]
Figure imgf000083_0002
Figure imgf000084_0001
As seen in Table 2, the complexes according to the present invention exhibited superior electroluminescence characteristics as compared to the existing material. Driving voltage of the device was decreased by 2 V or more and power efficiency was improved by 2.6 times or more as compared to the existing material (Comparative Example
1) . Especially, the device of Example 3 was operated at a voltage
3.1 V lower than that of Comparative Example 1, and the device of
Example 8 exhibited a driving voltage of 4.5 V and a power efficiency of 6.3 lm/W at 1000 cd/m2.
Accordingly, the device using the electroluminescent compound according to the present invention as host material has excellent electroluminescence characteristics and power consumption can be improved by increasing power efficiency by 1.9-3.9 lm/W through decreased driving voltage. [industrial Applicability]
When used for a host material of an electroluminescent material in an OLED device, the electroluminescent compound according to the present invention provides better red luminous efficiency as compared to existing host materials and excellent life property of the material . Therefore, it can be used tomanufacture OLEDs having very good operation life.
While the exemplary embodiments have been shown and described, it will be understood by those skilled in the art that various changes in form and details may be made thereto without departing from the spirit and scope of this disclosure as defined by the appended claims. In addition, many modifications can be made to adapt a particular situation or material to the teachings of this disclosure without departing from the essential scope thereof . Therefore, it is intended that this disclosure not be limited to the particular exemplary embodiments disclosed as the best mode contemplated for carrying out this disclosure, but that this disclosure will include all embodiments falling within the scope of the appended claims.

Claims

[CLAIMS]
[Claim l]
An electroluminescent compound represented by Chemical Formula
1:
Figure imgf000086_0001
wherein
M represents a divalent or trivalent metal; n represents the cationic valence of M;
Ri through R8 independently represent hydrogen, (C1-C60) alkyl, halogen, cyano, (C3-C60) cycloalkyl, 5- or 6-memberedheterocycloalkyl containing one or more heteroatom (s) selected from N, 0 and S,
(C7-C60)bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl,
(C6-C60)aryl, (C1-C60) alkoxy, (C1-C60) alkylthio, (C6-C60) aryloxy,
(C3-C60) heteroaryl containing one or more heteroatom (s) selected from N, O and S, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl,
(C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino, tri (Cl-C30)alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, di (C6-C60) arylboranyl, di (C1-C60) alkylboranyl, carboxyl, nitro or hydroxyl; and the alkyl, cycloalkyl, heterocycloalkyl, bicycloalkyl, adamantyl, alkenyl, alkynyl, aryl, alkoxy, alkylthio, aryloxy, heteroaryl, arylthio, alkoxycarbonyl, alkylcarbonyl, arylcarbonyl, alkylamino, arylamino, trialkylsilyl, dialkylarylsilyl, triarylsilyl, diarylboranyl or dialkylboranyl of Ri through R8 may be further substituted by one or more substituent (s) selected from a group consisting of (C1-C60) alkyl, halogen, cyano, (C3-C60) cycloalkyl, 5- or 6-membered heterocycloalkyl containing one or more heteroatom (s) selected from N, O and S, (C7-C60) bicycloalkyl, adamantyl, (C2-C60) alkenyl, (C2-C60) alkynyl, (C6-C60) aryl, (Cl-CβO)alkoxy, (C1-C60) alkylthio, (C6-C60) aryloxy, (C3-C60) heteroaryl containing one or more heteroatom (s) selected from N, 0 and S, (C6-C60) arylthio, (C1-C60) alkoxycarbonyl, (C1-C60) alkylcarbonyl, (C6-C60) arylcarbonyl, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, carboxyl, nitro and hydroxyl, except for the case where all of Ri through Rg are hydrogens.
[Claim 2]
The electroluminescent compound according to claim 1, wherein M represents a divalent metal selected from a group consisting of Be, Zn, Mg, Ca, Cu and Ni.
[Claim 3]
The electroluminescent compound according to claim 1, wherein M represents a trivalent metal selected from a group consisting of Al, In, Co, Ga and B.
[Claim 4]
An electroluminescent device comprising the electroluminescent compound according to any of claims 1 to 3.
[Claim 5]
The electroluminescent device according to claim 4, 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 electroluminescent compound (s) according to any of claims 1 to 3 and one or more dopant (s) represented by Chemical Formula 2:
MlL101L102L103 ( 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 imgf000088_0001
Figure imgf000089_0001
wherein
Rn through R13 independently represent hydrogen, (C1-C60) alkyl with or without halogen substituent, (C6-C60)aryl with or without (C1-C60) alkyl substituent or halogen;
Ri4 through R29 independently represent hydrogen, (C1-C60) alkyl,
(Cl-C30)alkoxy, (C3-C60) cycloalkyl, (C2-C30) alkenyl, (C6-C60) aryl, mono- or di (C1-C30) alkylamino, mono- or di (C6-C30) arylamino, SF5, tri (C1-C30) alkylsilyl, di (C1-C30) alkyl (C6-C30) arylsilyl, tri (C6-C30) arylsilyl, cyano or halogen, and the alkyl, cycloalkyl, alkenyl or aryl of Ri4 through R2g may be further substituted by one or more substituent (s) selected from (C1-C60) alkyl, (C6-C60) aryl and halogen; R30 through R33 independently represent hydrogen, (C1-C60) alkyl with or without halogen substituent or (C6-C60)aryl with or without
(C1-C60) alkyl substituent;
R34 and R35 independently represent hydrogen, (C1-C60) alkyl,
(C6-C60) aryl or halogen, OrR34 andR35 maybe linkedvia (C3-C12) alkylene or (C3-C12) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring, and the alkyl or aryl of R34 and R35, or the alicyclic ring or the monocyclic or polycyclic aromatic ring formed as they are linked via (C3-C12) alkylene or
(C3-C12) alkenylene with or without a fused ring may be further substituted by one or more substituent (s) selected from (C1-C60) alkyl with or without halogen substituent, (C1-C30) alkoxy, halogen, tri(Cl-C30)alkylsilyl, tri (C6-C30) arylsilyl and (C6-C60) aryl;
R36 represents (C1-C60) alkyl, (C6-C60) aryl, (C5-C60) heteroaryl containing one or more heteroatom (s) selected fromN, 0 and S or halogen; R37 through R39 independently represent hydrogen, (C1-C60) alkyl,
(C6-C60)aryl or halogen, and the alkyl or aryl of R36 through R39 may be further substituted halogen or (C1-C60) alkyl;
R40 and R41 independently represent hydrogen, (C1-C20) alkyl with or without halogen substituent, (C6-C20) aryl, halogen, cyano, tri(Cl-C20)alkylsilyl, di (C1-C20) alkyl (C6-C20) arylsilyl, tri (C6-C20) arylsilyl, (C1-C20) alkoxy, (C1-C20) alkylcarbonyl, (Cβ-C20)arylcarbonyl, di (C1-C20) alkylamino or di (C6-C20) arylamino, or R40 and R4I may be linked via (C3-C12 ) alkylene or (C3-C12) alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring; the alkyl or aryl of R40 and R4i, or the alicyclic ring or the monocyclic or polycyclic aromatic ring formed as they are linked via
(C3-C12) alkylene or (C3-C12) alkenylene with or without a fused ring may be further substituted by one or more substituent (s) selected from (C1-C20) alkyl with or without halogen substituent, halogen, cyano, tri(Cl-C20)alkylsilyl, di (C1-C20) alkyl (C6-C20) arylsilyl, tri(C6-C20)arylsilyl, (C1-C20) alkoxy, (C1-C20) alkylcarbonyl,
(C6-C20) arylcarbonyl, di (C1-C20) alkylamino, di (C6-C20) arylamino, phenyl, naphthyl, anthryl, fluorenyl and spirobifluorenyl, or may be further substituted by phenyl or fluorenyl with one or more substituent (s) selected from a group consisting of (C1-C20) alkyl with or without halogen substituent , halogen, cyano, tri (C1-C20) alkylsilyl, di (C1-C20) alkyl (C6-C20) arylsilyl, tri (C6-C20) arylsilyl,
(C1-C20) alkoxy, (C1-C20) alkylcarbonyl, (C6-C20) arylcarbonyl, di (C1-C20) alkylamino, di (C6-C20) arylamino, phenyl, naphthyl, anthryl, fluorenyl, and spirobifluorenyl;
R42 through R4g independently represent hydrogen, (C1-C20) alkyl with or without halogen substituent, (C1-C20) alkoxy,
(C3-C12)cycloalkyl, halogen, cyano, (C6-C20) aryl,
(C4-C20) heteroaryl, tri (C1-C20) alkylsilyl, di (C1-C20) alkyl (C6-C20) arylsilyl or tri (C6-C20) arylsilyl; and Q represents \ / ,
Figure imgf000092_0001
Or , wherein R51 through R62 independently represent hydrogen, (C1-C60) alkyl with or without halogen substituent, (C1-C30) alkoxy, halogen, (C6-C60) aryl, cyano or (C5-C60) cycloalkyl, ore each of R51 through Rβ2 may be linked to an adjacent substituent via alkylene or alkenylene to form a (C5-C7)spiro ring or a (C5-C9) fused ring, or may be linked to Ri7 or Ri8 via alkylene or alkenylene to form a (C5-C7) fused ring. [Claim 6]
The electroluminescent device according to claim 5, wherein the organic layer comprises one or more compound (s) selected from a group consisting of arylamine compounds and styrylarylamine compounds. [Claim 7]
The electroluminescent device according to claim 5, wherein the organic layer further comprises 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 . [Claim 8]
The electroluminescent device according to claim 5, wherein the organic comprises an electroluminescent layer and a charge generating layer . [Claim 9]
A white-emitting electroluminescent device comprising the electroluminescent compound according to any of claims 1 to 3. [Claim 10]
An organic solar cell comprising the electroluminescent compound according to any of claims 1 to 3.
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KR100901888B1 (en) 2009-06-09
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