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EP2616462A1 - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same

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Publication number
EP2616462A1
EP2616462A1 EP11825442.4A EP11825442A EP2616462A1 EP 2616462 A1 EP2616462 A1 EP 2616462A1 EP 11825442 A EP11825442 A EP 11825442A EP 2616462 A1 EP2616462 A1 EP 2616462A1
Authority
EP
European Patent Office
Prior art keywords
substituted
unsubstituted
alkyl
aryl
organic electroluminescent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP11825442.4A
Other languages
German (de)
French (fr)
Other versions
EP2616462A4 (en
Inventor
Hyo Nim Shin
Soo-Jin Hwang
Hee Sook Kim
Seok Keun Yoon
Mi Ja Lee
Nam Kyun Kim
Young Jun Cho
Hyuck Joo Kwon
Kyung Joo Lee
Bong Ok Kim
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rohm and Haas Electronic Materials Korea Ltd
Original Assignee
Rohm and Haas Electronic Materials Korea Ltd
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Publication date
Application filed by Rohm and Haas Electronic Materials Korea Ltd filed Critical Rohm and Haas Electronic Materials Korea Ltd
Publication of EP2616462A1 publication Critical patent/EP2616462A1/en
Publication of EP2616462A4 publication Critical patent/EP2616462A4/en
Withdrawn legal-status Critical Current

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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C07D403/02—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
    • 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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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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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
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    • 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
    • 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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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission

Definitions

  • the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device including the same.
  • electroluminescent (EL) devices which are self-emissive display devices, are advantageous in that they provide wide viewing angle, superior contrast and a fast response rate.
  • EL electroluminescent
  • Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [ Appl. Phys. Lett. 51, 913, 1987].
  • electroluminescent material The most important factor to determine luminous efficiency in an organic light-emitting diode (OLED) is electroluminescent material.
  • fluorescent materials have been widely used as electroluminescent material up to the present, development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to four (4) times, in view of electroluminescent mechanism.
  • iridium (III) complexes have been widely known as phosphorescent material, including (acac)Ir(btp) 2 , Ir(ppy) 3 and Firpic, as the red, green and blue one, respectively.
  • a lot of phosphorescent materials have been recently investigated in Japan, Europe and America.
  • CBP is most widely known as a host material for a phosphorescent material.
  • High-efficiency OLEDs using a hole blocking layer comprising BCP, BAlq, etc. are reported.
  • High-performance OLEDs using BAlq derivatives as a host were reported by Pioneer (Japan) and others.
  • an 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 material.
  • Another object of the present invention is to provide an organic electroluminescent device having high efficiency and a long life using the organic electroluminescent compound as an electroluminescent material.
  • organic electroluminescent compound represented by Chemical Formula 1 below, and an organic electroluminescent device using the same.
  • the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life and consuming less power due to improved power efficiency.
  • ring A represents a monocyclic or polycyclic aromatic ring
  • X 1 and X 2 independently represent N or CR';
  • L 1 represents a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C2-C30)heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;
  • Ar 1 represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C2-C30)heteroaryl;
  • Z is independently selected from following structures
  • Z is selected from following structures only when the ring A is a monocyclic aromatic ring;
  • Y represents -O-, -S-, -C(R 11 R 12 )-, -Si(R 13 R 14 )- or -N(R 15 )-;
  • R 1 through R 9 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30)ar(C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl fused with substituted or unsubstituted one or more aromatic rings, (C3-C30)cycloalkyl fused with substituted or unsubstituted one or more aromatic rings, -NR 16 R 17
  • R' and R 11 through R 22 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl or substituted or unsubstituted (C3-C30)cycloalkyl, or they may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and a carbon atom of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatom(s) selected from the group consisting of
  • a, c, e and i independently represent an integer of 1 to 4, and when a, c, e and I are an integer of 2 or greater, each of R 1 , R 3 , R 5 and R 9 may be identical or different from each other;
  • b, d, and g independently represent an integer of 1 to 3, and when b, d, and g are an integer of 2 or greater, each R 2 , R 4 and R 7 may be identical or different from each other;
  • f represents an integer of 1 to 6, and when f is an integer of 2 or greater, each R 6 may be identical or different from each other;
  • h represents an integer of 1 to 5, and when h is an integer of 2 or greater, each R 8 may be identical or different from each other;
  • alkyl As described herein, “alkyl”, “alkoxy” and other substituents containing the “alkyl” moiety include both linear and branched species, and the “cycloalkyl” includes polycyclic hydrocarbon ring such as substituted or unsubstituted adamantyl or substituted or unsubstituted (C7-C30)bicycloalkyl as well as a monocyclic hydrocarbon ring.
  • aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly, 5- or 6-membered, single ring or fused ring, and even further includes a structure where a plurality of aryls are linked by single bond(s). Specific examples thereof include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
  • the naphthyl includes 1-naphthyl and 2-naphthyl
  • the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl
  • the phenanthryl includes 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl and 9-phenanthryl
  • the naphthacenyl includes 1-naphthacenyl, 2-naphthacenyl and 9-naphthacenyl.
  • the pyrenyl includes 1-pyrenyl, 2-pyrenyl and 4-pyrenyl
  • the biphenyl includes 2-biphenyl, 3-biphenyl and 4-biphenyl
  • the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl
  • the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • heteroaryl includes a structure where one or more heteroaryls are linked by single bonds.
  • 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 thereof include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, or the like, polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl
  • the pyrrolyl includes 1-pyrrolyl, 2-pyrrolyl and 3-pyrrolyl; the pyridyl includes 2-pyridyl, 3-pyridyl and 4-pyridyl; the indolyl includes 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl and 7-indolyl; the isoindolyl includes 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl and 7-isoindolyl; the furyl includes 2-furyl and 3-furyl; the benzofuranyl includes 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl and 7-benzofuranyl; the isobenzofur
  • (C1-C30)alkyl includes (C1-C20)alkyl or (C1-C10)alkyl
  • (C6-C30)aryl includes (C6-C20)aryl
  • (C2-C30)heteroaryl includes (C2-C20)heteroaryl
  • (C3-C30)cycloalkyl includes (C3-C20)cycloalkyl or (C3-C7)cycloalkyl.
  • (C2-C30)alkenyl or alkynyl includes (C2-C20)alkenyl or alkynyl, or (C2-C10)alkenyl or alkynyl.
  • each substituent of the L 1 , Ar 1 , R 1 through R 9 , R and R 11 through R 22 may be further substituted by one or more substituent(s) selected from the group consisting of deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, (C6-C30)aryl, (C6-C30)aryl-substituted or unsubstituted (C2-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic rings, R a R b R c Si-, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, -NR d R e , -BR
  • the organic electroluminescent compound may be represented by Chemical Formulas 2 to 9 below.
  • X 2 is N or CH; Y is -O-, -S-, -C(R 11 R 12 )- or -N(R 15 )-; L 1 represents a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (C2-C30)heteroarylene; Ar 1 represents hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C2-C30)heteroaryl; R 1 through R 9 independently represent hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, NR 16 R 17 or SiR 18 R 19 R 20 ; R 11 , R 12 , R 15 and R 16 through R 20 independently represent hydrogen, deuterium, substituted substituted
  • X 2 represents N or CH;
  • Y represents -O-, -S-, -C(R 11 R 12 )- or -N(R 15 )-;
  • L 1 represents a single bond or arylene selected from the following structures:
  • R 31 and R 32 independently represent methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, pyridyl or quinolyl;
  • Ar 1 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, terphenyl, naphthyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, fluoranthenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or N-phenylcarbazoly
  • R 1 through R 9 independently represent hydrogen, deuterium, phenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, amino or carbazolyl;
  • R 11 , R 12 and R 15 independently represent hydrogen, deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, 9,9-diphenylfluorenyl, 9,
  • organic electroluminescent compound according to the present invention may be exemplified by the following compounds, which are not intended to limit the present invention.
  • organic electroluminescent compound according to the present invention may be prepared as shown in, for example, Scheme 1 below, but is not limited thereto.
  • an organic electroluminescent device which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compounds represented by Chemical Formula 1.
  • the organic layer includes an electroluminescent layer, and the organic electroluminescent compound of Chemical Formula 1 may be used as a host in the electroluminescent layer.
  • the organic electroluminescent compound of Chemical Formula 1 when used as a host, one or more phosphorescent dopant(s) is included.
  • the phosphorescent dopant applied to the organic electroluminescent device according to the present invention is not specifically limited, but may be selected from among compounds represented by Chemical Formula 10 below.
  • M 1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16 of the Periodic table, and ligands L 101 , L 102 and L 103 are independently selected from the following structures:
  • R 201 through R 203 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl or halogen;
  • R 204 through R 219 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, SF 5 , substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl,
  • R 220 through R 223 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, or (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl;
  • R 224 and R 225 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl 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 alicyclic ring and a monocyclic or polycyclic aromatic ring;
  • R 226 represents substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, or halogen;
  • R 227 through R 229 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or halogen;
  • Q represents , or ;
  • R 231 through R 242 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkoxy, halogen, substituted or unsubstituted (C6-C30)aryl, cyano or substituted or unsubstituted (C3-C30)cycloalkyl, or they 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.
  • the dopant compound of Chemical Formula 10 may be exemplified by the following compounds, but is not limited thereto.
  • the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
  • the arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s).
  • the organic layer may include an electroluminescent layer and a charge generating layer.
  • the organic layer may include, in addition to the organic electroluminescent compound of Chemical Formula 1, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device.
  • the compounds emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • a layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. Operation stability may be attained therefrom.
  • the chalcogenide may be, for example, 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.
  • the organic electroluminescent device it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant.
  • a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant.
  • the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated.
  • the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated.
  • Preferable oxidative dopants include various Lewis acids and acceptor compounds.
  • Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
  • an organic electroluminescent compound can exhibit high luminous efficiency and can have excellent material life, and can be used to manufacture OLED devices having very superior operating life.
  • Compound 2-2 (9.5g, 19.1mmol, 74%) was prepared by the same method as in the preparation of Compound 1-2 .
  • Compound 2-3 (9.0g, 15.6mmol, 82%) was prepared by the same method as in the preparation of Compound 1-3 .
  • Compound 2-4 (4.0g, 7.4mmol, 47%) was prepared by the same method as in the preparation of Compound 1-4 .
  • Compound 2 (2.8g, 4.6mmol, 51%) was prepared from Compound 2-4 (4.0g, 7.4mmol) and 3-bromo-9-phenyl-9H-carbazole (6.7g, 20.88mmol) by the same method as in the preparation of Compound 1 .
  • Compound 7 (2.8g, 4.6mmol, 51%) was prepared from Compound 2-4 (4.0g, 7.4mmol) and 2-bromodibenzo[b,d]thiophene (5.5g, 20.88mmol) by the same method as in the preparation of Compound 1 .
  • Compound 12 (6.8g, 9.5mmol, 53%) was prepared from Compound 1-4 (6.9g, 18.05mmol) and 10-bromo-7-phenyl-7H-benzo[c]carbazole (7.8g, 20.88mmol) by the same method as in the preparation of Compound 1 .
  • Compound 16 (7.6g, 11.0mmol, 61%) was prepared from Compound 2-4 (9.8g, 18.05mmol) and 2-bromo-9,9-dimethyl-9H-fluorene (5.7g, 20.88mmol) by the same method as in the preparation of Compound 1 .
  • Compound 6-4 (4.3g, 7.5mmol, 76%) was prepared by the same method as in the preparation of Compound 1-3 .
  • Compound 6-5 (1.7g, 3.1mmol, 43%) was prepared by the same method as in the preparation of Compound 1-4 .
  • Compound 25 (7.6g, 10.3mmol, 57%) was prepared from Compound 6-5 (9.8g, 18.05mmol) and 3-bromo-9-phenyl-9H-carbazole (6.7g, 20.88mmol) by the same method as in the preparation of Compound 1 .
  • An OLED device was manufactured using the compound for organic electronic materials 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 deposition apparatus, and N 1 ,N 1' ([1,1'-biphenyl]-4,4'-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4 -diphenylbenzene-1,4-diamine was placed in a cell of the vacuum deposition apparatus, which was then evacuated up to 10 -6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate it, thereby depositing a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was placed in another cell of the vacuum deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby depositing a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • an electroluminescent layer was formed thereon as follows. Compound 1 as a host was placed in a cell, and Compound D-11 as a dopant was placed in another cell, within a vacuum vapor deposition apparatus.
  • the two materials were evaporated at different rates such that 4 wt% doping taken place, and thereby the electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer. Subsequently, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was placed in a cell and lithium quinolate was placed in another cell, after which the two materials were evaporated at the same rate such that 50 wt% doping taken place, and thereby an electron transport layer was vapor-deposited to a thickness of 30 nm on the electroluminescent layer.
  • Liq lithium quinolate
  • Al cathode was vapor-deposited to a thickness of 150 nm using another vacuum vapor deposition apparatus to manufacture an OLED.
  • Each compound used in the OLED device was purified by vacuum sublimation at 10 -6 torr before use.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 2 was used as the host material, and D-7 was used as a dopant in the electroluminescent layer.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 25 was used as the host material in the electroluminescent layer.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 37 was used as the host material, and D-7 was used as a dopant in the electroluminescent layer.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 128 was used as the host material, and D-7 was used as a dopant in the electroluminescent layer.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 139 was used as the host material, and D-7 was used as a dopant in the electroluminescent layer.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that an electroluminescent layer was vapor-deposited using 4,4'-N,N'-dicarbazole-biphenyl used as a host and Compound D-11 as a dopant, and a hole blocking layer was vapor-deposited to a thickness of 10 nm using aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate between the electroluminescent layer and the electron transport layer.
  • the organic electroluminescent compounds developed in the present invention showed superior electroluminescent properties compared to the conventional material.
  • the devices using the organic electroluminescent compounds of the present invention as a host material can exhibit superior electroluminescent properties and can reduce operating voltage to thus increase power efficiency, thereby improving power consumption.
  • an organic electroluminescent compound can exhibit high luminous efficiency and can have excellent material life, and can be used to manufacture OLED devices having very superior operating life.

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Abstract

Provided are novel organic electroluminescent compounds and an organic electroluminescent device using the same. Because the organic electroluminescent compound disclosed herein exhibits good luminous efficiency and an excellent life performance, it may be used to manufacture OLED devices very superior in terms of operating life and which consume less power due to improved power efficiency.

Description

    NOVEL ORGANIC ELECTROLUMINESCENT COMPOUNDS AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
  • The present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device including the same.
    •
  • Among display devices, electroluminescent (EL) devices, which are self-emissive display devices, are advantageous in that they provide wide viewing angle, superior contrast and a fast response rate. In 1987, Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [Appl. Phys. Lett. 51, 913, 1987].
  • The most important factor to determine luminous efficiency in an organic light-emitting diode (OLED) is electroluminescent material. Though fluorescent materials have been widely used as electroluminescent material up to the present, development of phosphorescent materials is one of the best ways to improve the luminous efficiency theoretically up to four (4) times, in view of electroluminescent mechanism. Up to now, iridium (III) complexes have been widely known as phosphorescent material, including (acac)Ir(btp)2, Ir(ppy)3 and Firpic, as the red, green and blue one, respectively. In particular, a lot of phosphorescent materials have been recently investigated in Japan, Europe and America.
  • At present, CBP is most widely known as a host material for a phosphorescent material. High-efficiency OLEDs using a hole blocking layer comprising BCP, BAlq, etc. are reported. High-performance OLEDs using BAlq derivatives as a host were reported by Pioneer (Japan) and others.
  • 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 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. Furthermore, the life of an OLED device using such a material is not satisfactory.
  • On the other hand, International Patent Publication No. WO 2006/049013 discloses a compound for an organic electroluminescent material the backbone of which has a fused bicyclic group. However, this literature does not specifically disclose a compound having both a carbazole backbone substituted with cycloalkyl or heterocycloalkyl that is fused with an aromatic ring and a nitrogen-containing fused bicyclic group.
    •
  • Therefore, the present invention has been made keeping in mind the problems occurring in the related art and an 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 material.
  • Another object of the present invention is to provide an organic electroluminescent device having high efficiency and a long life using the organic electroluminescent compound as an electroluminescent material.
    •
  • Provided are compounds for organic electroluminescent compound represented by Chemical Formula 1 below, and an organic electroluminescent device using the same. With superior luminescence efficiency and excellent life property, the organic electroluminescent compound according to the present invention may be used to manufacture an OLED device having very superior operation life and consuming less power due to improved power efficiency.
  • [Chemical Formula 1]
  • wherein,
  • ring A represents a monocyclic or polycyclic aromatic ring;
  • X1 and X2 independently represent N or CR';
  • L1 represents a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C2-C30)heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;
  • Ar1 represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C2-C30)heteroaryl;
  • Z is independently selected from following structures;
  • but Z is selected from following structures only when the ring A is a monocyclic aromatic ring;
  • Y represents -O-, -S-, -C(R11R12)-, -Si(R13R14)- or -N(R15)-;
  • R1 through R9 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30)ar(C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl fused with substituted or unsubstituted one or more aromatic rings, (C3-C30)cycloalkyl fused with substituted or unsubstituted one or more aromatic rings, -NR16R17, -SiR18R19R20, -SR21, -OR22, cyano, nitro or hydroxyl, or R1 through R9 may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and a carbon atom of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatom(s) selected from the group consisting of N, O and S;
  • R' and R11 through R22 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl or substituted or unsubstituted (C3-C30)cycloalkyl, or they may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and a carbon atom of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatom(s) selected from the group consisting of N, O and S;
  • a, c, e and i independently represent an integer of 1 to 4, and when a, c, e and I are an integer of 2 or greater, each of R1, R3, R5 and R9 may be identical or different from each other;
  • b, d, and g independently represent an integer of 1 to 3, and when b, d, and g are an integer of 2 or greater, each R2, R4 and R7 may be identical or different from each other;
  • f represents an integer of 1 to 6, and when f is an integer of 2 or greater, each R6 may be identical or different from each other;
  • h represents an integer of 1 to 5, and when h is an integer of 2 or greater, each R8 may be identical or different from each other; and
  • the heteroaromatic ring, heteroarylene, heterocycloalkyl and heteroaryl include one or more heteroatom(s) selected from the group consisting of B, N, O, S, P(=O), Si and P.
  • As described herein, "alkyl", "alkoxy" and other substituents containing the "alkyl" moiety include both linear and branched species, and the "cycloalkyl" includes polycyclic hydrocarbon ring such as substituted or unsubstituted adamantyl or substituted or unsubstituted (C7-C30)bicycloalkyl as well as a monocyclic hydrocarbon ring. As described herein, "aryl" means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly, 5- or 6-membered, single ring or fused ring, and even further includes a structure where a plurality of aryls are linked by single bond(s). Specific examples thereof include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto. The naphthyl includes 1-naphthyl and 2-naphthyl, the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl, the phenanthryl includes 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl and 9-phenanthryl, and the naphthacenyl includes 1-naphthacenyl, 2-naphthacenyl and 9-naphthacenyl. The pyrenyl includes 1-pyrenyl, 2-pyrenyl and 4-pyrenyl, and the biphenyl includes 2-biphenyl, 3-biphenyl and 4-biphenyl, the terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl, and the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • The "heteroaryl" described herein means an aryl group containing 1 to 4 heteroatom(s) selected from the group consisting of B, N, O, S, P(=O), Si and P as aromatic ring backbone atom(s) and the remaining aromatic ring backbone atom is carbon. It may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl condensed with one or more benzene ring(s), and may be partially saturated. In the present invention, "heteroaryl" includes a structure where one or more heteroaryls are linked by single bonds. 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 thereof include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, or the like, polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, benzodioxolyl, acridinyl, phenanthrolinyl, phenazinyl, phenothiazinyl, phenoxazinyl or the like, N-oxide thereof (e.g., pyridyl N-oxide, quinolyl N-oxide), quaternary salt thereof, and the like, but are not limited thereto.
  • The pyrrolyl includes 1-pyrrolyl, 2-pyrrolyl and 3-pyrrolyl; the pyridyl includes 2-pyridyl, 3-pyridyl and 4-pyridyl; the indolyl includes 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl and 7-indolyl; the isoindolyl includes 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl and 7-isoindolyl; the furyl includes 2-furyl and 3-furyl; the benzofuranyl includes 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl and 7-benzofuranyl; the isobenzofuranyl includes 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl, 5-isobenzofuranyl, 6-isobenzofuranyl and 7-isobenzofuranyl; the quinolyl includes 3-quinolyl, 4-quinolyl, 5-quinolyl, 6-quinolyl, 7-quinolyl and 8-quinolyl; the isoquinolyl includes 1-isoquinolyl, 3-isoquinolyl, 4-isoquinolyl, 5-isoquinolyl, 6-isoquinolyl, 7-isoquinolyl and 8-isoquinolyl; the quinoxalinyl includes 2-quinoxalinyl, 5-quinoxalinyl and 6-quinoxalinyl; the carbazolyl includes 1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl and 9-carbazolyl; the phenanthridinyl includes 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl and 10-phenanthridinyl; the acridinyl includes 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl and 9-acridinyl; the phenanthrolinyl includes 1,7-phenanthrolin-2-yl, 1,7-phenanthrolin-3-yl, 1,7-phenanthrolin-4-yl, 1,7-phenanthrolin-5-yl, 1,7-phenanthrolin-6-yl, 1,7-phenanthrolin-8-yl, 1,7-phenanthrolin-9-yl, 1,7-phenanthrolin-10-yl, 1,8-phenanthrolin-2-yl, 1,8-phenanthrolin-3-yl, 1,8-phenanthrolin-4-yl, 1,8-phenanthrolin-5-yl, 1,8-phenanthrolin-6-yl, 1,8-phenanthrolin-7-yl, 1,8-phenanthrolin-9-yl, 1,8-phenanthrolin-10-yl, 1,9-phenanthrolin-2-yl, 1,9-phenanthrolin-3-yl, 1,9-phenanthrolin-4-yl, 1,9-phenanthrolin-5-yl, 1,9-phenanthrolin-6-yl, 1,9-phenanthrolin-7-yl, 1,9-phenanthrolin-8-yl, 1,9-phenanthrolin-10-yl, 1,10-phenanthrolin-2-yl,1,10-phenanthrolin-3-yl, 1,10-phenanthrolin-4-yl, 1,10-phenanthrolin-5-yl, 2,9-phenanthrolin-1-yl, 2,9-phenanthrolin-3-yl, 2,9-phenanthrolin-4-yl, 2,9-phenanthrolin-5-yl, 2,9-phenanthrolin-6-yl, 2,9-phenanthrolin-7-yl, 2,9-phenanthrolin-8-yl, 2,9-phenanthrolin-10-yl, 2,8-phenanthrolin-1-yl, 2,8-phenanthrolin-3-yl, 2,8-phenanthrolin-4-yl, 2,8-phenanthrolin-5-yl, 2,8-phenanthrolin-6-yl, 2,8-phenanthrolin-7-yl, 2,8-phenanthrolin-9-yl, 2,8-phenanthrolin-10-yl, 2,7-phenanthrolin-1-yl, 2,7-phenanthrolin-3-yl, 2,7-phenanthrolin-4-yl, 2,7-phenanthrolin-5-yl, 2,7-phenanthrolin-6-yl, 2,7-phenanthrolin-8-yl, 2,7-phenanthrolin-9-yl and 2,7-phenanthrolin-10-yl; the phenazinyl includes 1-phenazinyl and 2-phenazinyl; the phenothiazinyl includes 1-phenothiazinyl, 2-phenothiazinyl, 3-phenothiazinyl, 4-phenothiazinyl and 10-phenothiazinyl; the phenoxazinyl includes 1-phenoxazinyl, 2-phenoxazinyl, 3-phenoxazinyl, 4-phenoxazinyl and 10-phenoxazinyl; the oxazolyl includes 2-oxazolyl, 4-oxazolyl and 5-oxazolyl; the oxadiazolyl includes 2-oxadiazolyl and 5-oxadiazolyl; the furazanyl includes 3-furazanyl; the dibenzofuranyl includes 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl and 4-dibenzofuranyl; and the dibenzothiophenyl includes 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl and 4-dibenzothiophenyl.
  • As described herein, the term "(C1-C30)alkyl" includes (C1-C20)alkyl or (C1-C10)alkyl, and the term "(C6-C30)aryl" includes (C6-C20)aryl. The term "(C2-C30)heteroaryl" includes (C2-C20)heteroaryl, and the term "(C3-C30)cycloalkyl" includes (C3-C20)cycloalkyl or (C3-C7)cycloalkyl. The term, "(C2-C30)alkenyl or alkynyl" includes (C2-C20)alkenyl or alkynyl, or (C2-C10)alkenyl or alkynyl.
  • In the expression "substituted or unsubstituted(or with or without substitutent(s))" used herein, "with substituted(with substitutent(s))" means that the unsubstituted substituent is further substituted with substituent(s). The each substituent of the L1, Ar1, R1 through R9, R and R11 through R22 may be further substituted by one or more substituent(s) selected from the group consisting of deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, (C6-C30)aryl, (C6-C30)aryl-substituted or unsubstituted (C2-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic rings, RaRbRcSi-, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, -NRdRe, -BRfRg, -PRhRi, -P(=O)RjRk, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, RlT-, RmC(=O)-, RmC(=O)O-, carboxyl, nitro and hydroxyl, wherein Ra through Rl independently represent (C1-C30)alkyl, (C6-C30)aryl or (C2-C30)heteroaryl; T is S or O; and Rm represents (C1-C30)alkyl, (C1-C30)alkoxy, (C6-C30)aryl, or (C6-C30)aryloxy.
  • The organic electroluminescent compound may be represented by Chemical Formulas 2 to 9 below.
  • [Chemical Formula 2]
  • [Chemical Formula 3]
  • [Chemical Formula 4]
  • [Chemical Formula 5]
  • [Chemical Formula 6]
  • [Chemical Formula 7]
  • [Chemical Formula 8]
  • [Chemical Formula 9]
  • wherein, X2 is N or CH; Y is -O-, -S-, -C(R11R12)- or -N(R15)-; L1 represents a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (C2-C30)heteroarylene; Ar1 represents hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C2-C30)heteroaryl; R1 through R9 independently represent hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, NR16R17 or SiR18R19R20; R11, R12, R15 and R16 through R20 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (C2-C30)heteroaryl, or R16 and R17 may be linked to via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring, and the carbon atom of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatom(s) selected from the group consisting of N, O and S.
  • To be specific, X2 represents N or CH; Y represents -O-, -S-, -C(R11R12)- or -N(R15)-;
  • L1 represents a single bond or arylene selected from the following structures:
  • ;
  • R31 and R32 independently represent methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, pyridyl or quinolyl;
  • Ar1 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, terphenyl, naphthyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, fluoranthenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or N-phenylcarbazolyl, and the phenyl, biphenyl, terphenyl, naphthyl and carbazolyl of Ar1 may be further substituted with one or more substituents selected from the group consisting of deuterium, fluorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, triphenylsilyl, trimethylsilyl, dimethylphenylsilyl, diphenylmethylsilyl, phenyl, naphthyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, phenylpyridyl, carbazolyl, fluoranthenyl, dibenzofuranyl, and dibenzothiophenyl; and
  • R1 through R9 independently represent hydrogen, deuterium, phenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, amino or carbazolyl; R11, R12 and R15 independently represent hydrogen, deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, naphthyl, pyridyl, N-phenylcarbazolyl or quinolyl, and the phenyl of R11, R12 and R15 may be further substituted with one or more substituents selected from the group consisting of deuterium, halogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl and naphthyl, and R11 and R12 may be linked to each other to form a ring.
  • The organic electroluminescent compound according to the present invention may be exemplified by the following compounds, which are not intended to limit the present invention.
  • The organic electroluminescent compound according to the present invention may be prepared as shown in, for example, Scheme 1 below, but is not limited thereto.
  • [Scheme 1]
  • In Scheme 1, ring A, X1, X2, L1, Ar1, R1, R2, R3, a, b, c and Z are the same as defined in Chemical Formula 1; and Hal represents halogen.
  • Provided is an organic electroluminescent device, which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compounds represented by Chemical Formula 1. The organic layer includes an electroluminescent layer, and the organic electroluminescent compound of Chemical Formula 1 may be used as a host in the electroluminescent layer.
  • In the electroluminescent layer, when the organic electroluminescent compound of Chemical Formula 1 is used as a host, one or more phosphorescent dopant(s) is included. The phosphorescent dopant applied to the organic electroluminescent device according to the present invention is not specifically limited, but may be selected from among compounds represented by Chemical Formula 10 below.
  • [Chemical Formula 10]
  • M1L101L102L103
  • wherein,
  • M1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16 of the Periodic table, and ligands L101, L102 and L103 are independently selected from the following structures:
  • R201 through R203 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl or halogen;
  • R204 through R219 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, SF5, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, cyano or halogen;
  • R220 through R223 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, or (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl;
  • R224 and R225 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl or halogen, or R224 and R225 may be linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
  • R226 represents substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, or halogen;
  • R227 through R229 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or halogen; and
  • Q represents , or ;
  • R231 through R242 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkoxy, halogen, substituted or unsubstituted (C6-C30)aryl, cyano or substituted or unsubstituted (C3-C30)cycloalkyl, or they may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring, or may be linked to R207 or R208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
  • The dopant compound of Chemical Formula 10 may be exemplified by the following compounds, but is not limited thereto.
  • In the organic electronic device of the present invention, the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, at the same time. The arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • Further, in the organic electroluminescent device of the present invention, the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compound(s). The organic layer may include an electroluminescent layer and a charge generating layer.
  • Further, the organic layer may include, in addition to the organic electroluminescent compound of Chemical Formula 1, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device. The compounds emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • In the organic electroluminescent device of the present invention, a layer (hereinafter referred to as "surface layer") selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a metal chalcogenide (including oxide) layer of silicon or aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be placed on the cathode surface of the electroluminescent medium layer. Operation stability may be attained therefrom. The chalcogenide may be, for example, SiOx (1 ≤ x ≤ 2), AlOx (1 ≤ x ≤ 1.5), SiON, SiAlON, etc. The metal halide may be, for example, LiF, MgF2, CaF2, a rare earth metal fluoride, etc. The metal oxide may be, for example, Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
  • In the organic electroluminescent device according to the present invention, it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant. In that case, since the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated. In addition, since the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated. Preferable oxidative dopants include various Lewis acids and acceptor compounds. Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
    •
  • According to the present invention, an organic electroluminescent compound can exhibit high luminous efficiency and can have excellent material life, and can be used to manufacture OLED devices having very superior operating life.
    •
  • Hereinafter, the present invention is further described by taking representative compounds of the present invention as examples of the organic electroluminescent compounds according to the invention, a preparing method thereof, and electroluminescent properties of the devices. But, those examples are provided only for the sake of illustrating the embodiments, and are not intended to limit the scope of the invention.
  • [Preparation Example 1] Preparation of Compound 1
  • Preparation of Compound 1-1
  • 2,4-dichloroquinazoline (8.1g, 40.6mmol), phenylboronic acid (5.0g, 40.6mmol), toluene 200mL, ethanol 50mL and water 50mL were mixed and then Pd(PPh3)4 (1.9g, 1.64mmol) and K2CO3 (12.9g, 122mmol) were added. The mixture was stirred at 120℃ for 5 hours and cooled to room temperature, after which the reaction was terminated with aqueous ammonium chloride 200mL. The mixture was extracted with ethyl acetate (EA) 500mL, and then washed with distilled water 50mL. The obtained organic layer was dried with anhydrous MgSO4, and the organic solvent was removed under reduced pressure. Subsequently, silica gel filtration and recrystallization were performed, yielding Compound 1-1 (6.6g, 68%).
  • Preparation of Compound 1-2
  • 7H-benzo[c]carbazole (8.9g, 41.10 mmol), Compound 1-1 (11.9g, 49.32mmol), Pd(OAc)2 (0.46g, NaOt-bu 7.9g, 82.20mmol), toluene 100mL, and P(t-bu)3 (2mL, 4.11mmol, 50% in toluene) were stirred under reflux. 10 hours later, the mixture was cooled to room temperature and distilled water was added. The resultant mixture was extracted with EA, dried with anhydrous MgSO4, and further dried under reduced pressure. Subsequently column separation was performed, yielding Compound 1-2 (14.5g, 84%).
  • Preparation of Compound 1-3
  • Compound 1-2 (14.3g, 33.98mmol) was placed into a one-neck flask, and a vacuum atmosphere was created and then the flask was filled with argon. THF 500mL was added and the mixture was stirred at 0℃ for 10 minutes. NBS (7.35g, 40.78mmol) was added and the mixture was stirred at room temperature for one day. The reaction was terminated, and the resulting mixture was extracted with distilled water and EA. The organic layer was dried with anhydrous MgSO4, the solvent was removed using a rotary evaporator, and then column chromatography using hexane and EA as developers was performed, yielding Compound 1-3 (14.6g, 85%).
  • Preparation of Compound 1-4
  • Compound 1-3 (13.2g, 26.30mmol) was placed into a one-neck flask, and a vacuum atmosphere was created and then the flask was filled with argon. THF 500mL was added and the mixture was stirred at -78℃ for 10 minutes. n-BuLi (2.5M in hexane) (15.8mL, 39.45mmol) was added in droplets and the mixture was stirred at -78℃ for 1 hour 30 minutes. Trimethylborate (4.85mL, 39.45mmol) was added at -78℃. The mixture was stirred at -78℃ for 30 minutes and then at room temperature for 4 hours. The reaction was terminated, and the resultant mixture was extracted with distilled water and EA. The organic layer was dried with anhydrous MgSO4, the solvent was removed using a rotary evaporator, and then column chromatography was conducted using hexane and EA as developers, yielding Compound 1-4 (6.9g, 18.05mmol, 65%).
  • Preparation of Compound 1
  • Compound 1-4 (8.1g, 17.4mmol), 3-bromo-9-phenyl-9H-carbazole (6.7g, 20.88mmol), Pd(PPh3)4 (0.8g, 0.7mmol), 2M K2CO3 aqueous solution 20mL, toluene 100mL, and ethanol 50mL were stirred under reflux for 12 hours. The mixture was washed with distilled water and extracted with EA. Drying with anhydrous MgSO4, distillation under reduced pressure and column separation were performed, yielding Compound 1 (6.8g, 10.3mmol, 58%).
  • MS/FAB: 663(found), 662.78(calculated)
  • [Preparation Example 2] Preparation of Compound 2
  • Preparation of Compound 2-1
  • 2,4-dichloroquinazoline (8.1g, 40.6mmol), biphenyl phenylboronic acid (8.0g, 40.6mmol), toluene 200mL, ethanol 50mL and water 50mL were mixed and Pd(PPh3)4 (1.9g, 1.64mmol) and K2CO3 (12.9g, 122mmol) were added. The mixture was stirred at 120℃ for 5 hours and cooled to room temperature, and the reaction was terminated with aqueous ammonium chloride 200mL. The mixture was extracted with EA 500mL, and washed with distilled water 50mL. The obtained organic layer was dried with anhydrous MgSO4, and the organic solvent was removed under reduced pressure. Subsequently, silica gel filtration and then recrystallization were performed, yielding Compound 2-1 (8.2g, 25.9mmol, 64%).
  • Preparation of Compound 2-2
  • Compound 2-2 (9.5g, 19.1mmol, 74%) was prepared by the same method as in the preparation of Compound 1-2.
  • Preparation of Compound 2-3
  • Compound 2-3 (9.0g, 15.6mmol, 82%) was prepared by the same method as in the preparation of Compound 1-3.
  • Preparation of Compound 2-4
  • Compound 2-4 (4.0g, 7.4mmol, 47%) was prepared by the same method as in the preparation of Compound 1-4.
  • Preparation of Compound 2
  • Compound 2 (2.8g, 4.6mmol, 51%) was prepared from Compound 2-4 (4.0g, 7.4mmol) and 3-bromo-9-phenyl-9H-carbazole (6.7g, 20.88mmol) by the same method as in the preparation of Compound 1.
  • MS/FAB: 739(found), 738.87(calculated)
  • [Preparation Example 3] Preparation of Compound 7
  • Preparation of Compound 7
  • Compound 7 (2.8g, 4.6mmol, 51%) was prepared from Compound 2-4 (4.0g, 7.4mmol) and 2-bromodibenzo[b,d]thiophene (5.5g, 20.88mmol) by the same method as in the preparation of Compound 1.
  • MS/FAB: 604(found), 603.73(calculated)
  • [Preparation Example 4] Preparation of Compound 12
  • Preparation of Compound 12
  • Compound 12 (6.8g, 9.5mmol, 53%) was prepared from Compound 1-4 (6.9g, 18.05mmol) and 10-bromo-7-phenyl-7H-benzo[c]carbazole (7.8g, 20.88mmol) by the same method as in the preparation of Compound 1.
  • MS/FAB: 713(found), 712.84(calculated)
  • [Preparation Example 5] Preparation of Compound 16
  • Preparation of Compound 16
  • Compound 16 (7.6g, 11.0mmol, 61%) was prepared from Compound 2-4 (9.8g, 18.05mmol) and 2-bromo-9,9-dimethyl-9H-fluorene (5.7g, 20.88mmol) by the same method as in the preparation of Compound 1.
  • MS/FAB: 690(found), 689.84(calculated)
  • [Preparation Example 6] Preparation of Compound 25
  • Preparation of Compound 6-1
  • 7H-benzo[c]carbazole (20g, 92mmol) and 1-bromo-4-iodobenzene (43.5g, 184mmol) were dissolved in toluene 500mL, and CuI (8.8g, 46 mmol), diaminoethane (6.2mL, 92mmol) and K3PO4 (8.7g, 276mmol) were added, and the mixture was refluxed for 30 hours. The mixture was cooled to room temperature, and the reaction was terminated with 2.0M aqueous HCl 50mL. The resultant mixture was extracted with EA 1L and then washed with distilled water 200mL. The obtained organic layer was dried with anhydrous MgSO4, and the organic solvent was removed under reduced pressure. Silica gel column chromatography was then conducted, yielding Compound 6-1 (19g, 56%).
  • Preparation of Compound 6-2
  • Compound 6-1 (19g, 51mmol) was dissolved in THF 250mL and then cooled to -78℃, and n-BuLi(2.5 M in hexane) (24.5mL) was added at -78℃. The mixture was stirred at -78℃ for 1 hour, and B(OMe)3 (8.5mL) was added, after which the mixture was stirred for 2 hours, and the reaction was terminated with aqueous ammonium chloride 100mL. The resultant mixture was extracted with EA 500mL and then washed with distilled water 100mL. The obtained organic layer was dried with anhydrous MgSO4, and the organic solvent was removed under reduced pressure. Recrystallization was then conducted, yielding Compound 6-2 (14g, 81%).
  • Preparation of Compound 6-3
  • Compound 1-1 (3.3g, 13.7mmol) and Compound 6-2 (5.5g, 16.4mmol) were mixed with toluene 100mL, ethanol 20mL and water 20mL, and Pd(PPh3)4 (1.6g, 1.4mmol) and K2CO3 (5.7g, 41.1mmol) were added. The mixture was stirred at 120℃ for 5 hours and cooled to room temperature, and the reaction was terminated with aqueous ammonium chloride 20mL. The mixture was extracted with EA 250mL and then washed with distilled water 30mL. The obtained organic layer was dried with anhydrous MgSO4, and the organic solvent was removed under reduced pressure. Silica gel filtration and recrystallization were then performed, yielding Compound 6-3 (4.9g, 9.8mmol, 72%).
  • Preparation of Compound 6-4
  • Compound 6-4 (4.3g, 7.5mmol, 76%) was prepared by the same method as in the preparation of Compound 1-3.
  • Preparation of Compound 6-5
  • Compound 6-5 (1.7g, 3.1mmol, 43%) was prepared by the same method as in the preparation of Compound 1-4.
  • Preparation of Compound 25
  • Compound 25 (7.6g, 10.3mmol, 57%) was prepared from Compound 6-5 (9.8g, 18.05mmol) and 3-bromo-9-phenyl-9H-carbazole (6.7g, 20.88mmol) by the same method as in the preparation of Compound 1.
  • MS/FAB: 739(found), 738.87(calculated)
  • [Preparation Example 7] Preparation of Compound 37
  • Preparation of Compound 7-1
  • 7H-benzo[c]carbazole (50g, 0.23mol) was dissolved in DMF 1.4L, and NBS (41g, 0.23mol) was added, after which the mixture was stirred at room temperature for 24 hours. After termination of the reaction, the resultant mixture was extracted with EA and the organic layer was distilled under reduced pressure. Silica column separation was then performed, yielding Compound 7-1 (53.2g, 78%).
  • Preparation of Compound 7-2
  • Compound 7-1 (30g, 0.10mol), iodobenzene (22.6mL, 0.20mmol), CuI (9.6g, 0.05mol), Cs2CO3 (99g, 0.030mol), and EDA (13.7mL, 0.20mol) were added to toluene 500mL and stirred under reflux for 24 hours. The mixture was extracted with EA, distilled under reduced pressure and column separated using MC/Hex, yielding Compound 7-2 (20g, 53%).
  • Preparation of Compound 7-3
  • Compound 7-2 (18g, 48.4mmol) was dissolved in THF 250mL, and 2.5M n-BuLi(in Hexane) (23.2mL, 58.0mmol) was added at -78℃ after which the mixture was stirred for 1 hour. B(Oi-Pr)3 (16.7mL, 72.5mmol) was slowly added and the solution was stirred for 2 hours. 2M HCl was added and the mixture was quenched and extracted with distilled water and EA. Recrystallization using MC and Hex was then conducted, yielding Compound 7-3 (13.6g. 83.4%).
  • Preparation of Compound 7-4
  • Compound 7-3 (13.6g, 40.3mmol), bromocarbazole (9.9g, 40.3mmol), Pd(PPh3)4 (2.3g, 2.0mmol), K2CO3 (13.4g, 96.7mmol), toluene 200mL and distilled water 48mL were mixed and then stirred at 90℃ for 2 hours. The organic layer was distilled under reduced pressure and triturated with MeOH. The obtained solid was dissolved in MC, silica filtered and triturated with MC and hexane, yielding Compound 7-4 (15g, 81%).
  • Preparation of Compound 37
  • Compound 1-1 (4g, 16.6mmol) and Compound 7-4 (7.6g, 16.6mmol) were suspended in DMF 80mL, and 60% NaH (1.1g, 28.2mmol) was added at room temperature and the mixture was stirred for 12 hours. Distilled water 1L was added and the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/EA, dissolved in MC, silica filtered and then triturated with MC/n-Hexane, yielding Compound 37 (2.4g, 21.8%).
  • MS/FAB found 662.78, calculated 662.25
  • [Preparation Example 8] Preparation of Compound 116
  • Preparation of Compound 8-1
  • Compound 7-1 (10 g, 33.8 mmol), dibenzo[b,d]furan-4-ylboronic acid (8.6 g, 40.56 mmol), Pd(PPh3)4 (2 g, 1.7mmol), K2CO3 (34 g, 321 mmol), toluene 60mL, EtOH 12mL and purified water 12mL were mixed and then stirred at 120℃ for 15 hours. After termination of the reaction, the resultant mixture was allowed to stand and the water layer was removed, after which the organic layer was concentrated. Silica column purification was then carried out, yielding Compound 8-1 (10.2 g, 78%).
  • Preparation of Compound 116
  • Compound 8-1 (3g, 7.8mmol) and Compound 2-1 (2.1g, 7.8mmol) were suspended in DMF 30mL, and 60% NaH (376mg, 9.4 mmol) was added at room temperature, and the mixture was stirred for 12 hours. Purified water 500mL was added and the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/EA, DMF and then EA/THF in that order. The resultant product was dissolved in MC, silica filtered, and triturated with MeOH/EA, yielding Compound 116 (2.4g, 46%).
  • MS/FAB found 663.76, calculated 663.23
  • [Preparation Example 9] Preparation of Compound 128
  • Preparation of Compound 9-1
  • 3-bromo-9H-carbazole (5g, 20.32mmol), dibenzo[b,d]furan-4-ylboronic acid (4.7g, 22.35mmol), K2CO3 (7g, 50.79mmol), Pd(PPh3)4 (1.17g, 1.01mmol), toluene 100mL, EtOH 25mL and purified water 25mL were mixed and then stirred at 100℃ for 3 hours. After termination of the reaction, the mixture was cooled to room temperature and allowed to stand and the water layer was removed. The organic layer was concentrated and then purified using a silica column, yielding Compound 9-1 (4.3g, 64%).
  • Preparation of Compound 128
  • Compound 2-1 (3g, 8.99mmol) and Compound 9-1 (3.14g, 9.89mmol) were suspended in anhydrous DMF 50mL, and 60% NaH (0.54g, 13.5mmol) was added at room temperature. The mixture was stirred at room temperature for 5 hours. After termination of the reaction, MeOH 3mL was added in droplets and the solid was obtained due to excessive MeOH, and silica column purification, suspending with EA, filtration and then crystallization with THF were performed, yielding Compound 128 (1g, 18%).
  • MS/FAB found 613.70, calculated 613.22
  • [Example 1] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
  • An OLED device was manufactured using the compound for organic electronic materials according to the present invention. First, a transparent electrode ITO thin film (15 Ω/□) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use. Then, an ITO substrate was equipped in a substrate folder of a vacuum deposition apparatus, and N1,N1'([1,1'-biphenyl]-4,4'-diyl)bis(N1-(naphthalen-1-yl)-N4,N4-diphenylbenzene-1,4-diamine was placed in a cell of the vacuum deposition apparatus, which was then evacuated up to 10-6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate it, thereby depositing a hole injection layer having a thickness of 60 nm on the ITO substrate. Subsequently, N,N'-di(4-biphenyl)-N,N'-di(4-biphenyl)-4,4'-diaminobiphenyl was placed in another cell of the vacuum deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby depositing a hole transport layer having a thickness of 20 nm on the hole injection layer. After forming the hole injection layer and the hole transport layer, an electroluminescent layer was formed thereon as follows. Compound 1 as a host was placed in a cell, and Compound D-11 as a dopant was placed in another cell, within a vacuum vapor deposition apparatus. The two materials were evaporated at different rates such that 4 wt% doping taken place, and thereby the electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer. Subsequently, 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole was placed in a cell and lithium quinolate was placed in another cell, after which the two materials were evaporated at the same rate such that 50 wt% doping taken place, and thereby an electron transport layer was vapor-deposited to a thickness of 30 nm on the electroluminescent layer. Subsequently, Liq (lithium quinolate) was vapor-deposited to a thickness of 2 nm as an electron injection layer, after which an Al cathode was vapor-deposited to a thickness of 150 nm using another vacuum vapor deposition apparatus to manufacture an OLED.
  • Each compound used in the OLED device was purified by vacuum sublimation at 10-6 torr before use.
  • As a result, it was confirmed that current of 8.8 mA/cm2 flows at voltage of 4.4 V and a red light of 900 cd/m2 was emitted.
  • [Example 2] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 2 was used as the host material, and D-7 was used as a dopant in the electroluminescent layer.
  • As a result, it was confirmed that current of 22.9 mA/cm2 flows at voltage of 4.9 V and a red light of 2710 cd/m2 was emitted.
  • [Example 3] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 25 was used as the host material in the electroluminescent layer.
  • As a result, it was confirmed that current of 16.9 mA/cm2 flows at voltage of 4.8 V and a red light of 1780 cd/m2 was emitted.
  • [Example 4] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 37 was used as the host material, and D-7 was used as a dopant in the electroluminescent layer.
  • As a result, it was confirmed that current of 41.2 mA/cm2 flows at voltage of 5.5 V and a red light of 4800 cd/m2 was emitted.
  • [Example 5] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 128 was used as the host material, and D-7 was used as a dopant in the electroluminescent layer.
  • As a result, it was confirmed that current of 8.7 mA/cm2 flows at voltage of 4.2 V and a red light of 900 cd/m2 was emitted.
  • [Example 6] Manufacture of OLED device using the organic electroluminescent compound according to the present invention
  • An OLED device was manufactured by the same method as in Example 1, with the exception that Compound 139 was used as the host material, and D-7 was used as a dopant in the electroluminescent layer.
  • As a result, it was confirmed that current of 3.2 mA/cm2 flows at voltage of 4.1 V and a red light of 400 cd/m2 was emitted.
  • [Comparative Example 1] Electroluminescent properties of OLED device using an electroluminescent material of the prior art.
  • An OLED device was manufactured by the same method as in Example 1, with the exception that an electroluminescent layer was vapor-deposited using 4,4'-N,N'-dicarbazole-biphenyl used as a host and Compound D-11 as a dopant, and a hole blocking layer was vapor-deposited to a thickness of 10 nm using aluminum(III)bis(2-methyl-8-quinolinato)4-phenylphenolate between the electroluminescent layer and the electron transport layer.
  • As a result, it was confirmed that current of 20.0 mA/cm2 flows at voltage of 8.2 V and a red light of 1000 cd/m2 was emitted.
  • It was confirmed that the organic electroluminescent compounds developed in the present invention showed superior electroluminescent properties compared to the conventional material. The devices using the organic electroluminescent compounds of the present invention as a host material can exhibit superior electroluminescent properties and can reduce operating voltage to thus increase power efficiency, thereby improving power consumption.
  • Although the preferred embodiments of the present invention have been disclosed for illustrative purposes, those skilled in the art will appreciate that various modifications, additions, and substitutions are possible, without departing from the scope and spirit of the invention as disclosed in the accompanying claims.
    •
  • According to the present invention, an organic electroluminescent compound can exhibit high luminous efficiency and can have excellent material life, and can be used to manufacture OLED devices having very superior operating life.
    •

Claims (10)

  1. An organic electroluminescent compound represented by Chemical Formula 1 below.
    [Chemical Formula 1]
    wherein,
    ring A represents a monocyclic or polycyclic aromatic ring;
    X1 and X2 independently represent N or CR';
    L1 represents a single bond, substituted or unsubstituted (C6-C30)arylene, substituted or unsubstituted (C2-C30)heteroarylene, or substituted or unsubstituted (C3-C30)cycloalkylene;
    Ar1 represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C2-C30)heteroaryl;
    Z is independently selected from following structures;
    but Z is selected from following structures only when the ring A is a monocyclic aromatic ring;
    Y represents -O-, -S-, -C(R11R12)-, -Si(R13R14)- or -N(R15)-;
    R1 through R9 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30)ar(C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl fused with substituted or unsubstituted one or more aromatic rings, (C3-C30)cycloalkyl fused with substituted or unsubstituted one or more aromatic rings, -NR16R17, -SiR18R19R20, -SR21, -OR22, cyano, nitro or hydroxyl, or R1 through R9 may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and a carbon atom of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatom(s) selected from the group consisting of N, O and S;
    R' and R11 through R22 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl or substituted or unsubstituted (C3-C30)cycloalkyl, or they may be linked to an adjacent substituent via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring, and a carbon atom of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatom(s) selected from the group consisting of N, O and S;
    a, c, e and i independently represent an integer of 1 to 4, and when a, c, e and I are an integer of 2 or greater, each of R1, R3, R5 and R9 may be identical or different from each other;
    b, d, and g independently represent an integer of 1 to 3, and when b, d, and g are an integer of 2 or greater, each R2, R4 and R7 may be identical or different from each other;
    f represents an integer of 1 to 6, and when f is an integer of 2 or greater, each R6 may be identical or different from each other;
    h represents an integer of 1 to 5, and when h is an integer of 2 or greater, each R8 may be identical or different from each other; and
    the heteroaromatic ring, heteroarylene, heterocycloalkyl and heteroaryl include one or more heteroatom(s) selected from the group consisting of B, N, O, S, P(=O), Si and P.
  2. The organic electroluminescent compound of claim 1, wherein each substituent of the L1, Ar1, R1 through R9, R and R11 through R22 is further substituted by one or more substituent(s) selected from the group consisting of deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, (C6-C30)aryl, (C6-C30)aryl-substituted or unsubstituted (C2-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic rings, RaRbRcSi-, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, -NRdRe, -BRfRg, -PRhRi, -P(=O)RjRk, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyl(C6-C30)aryl, RlT-, RmC(=O)-, RmC(=O)O-, carboxyl, nitro and hydroxyl, wherein Ra through Rl independently represent (C1-C30)alkyl, (C6-C30)aryl or (C2-C30)heteroaryl; T is S or O; and Rm represents (C1-C30)alkyl, (C1-C30)alkoxy, (C6-C30)aryl, or (C6-C30)aryloxy.
  3. The organic electroluminescent compound of claim 1, which is selected from the group consisting of compounds represented by Chemical Formulas 2 to 9 below.
    [Chemical Formula 2]
    [Chemical Formula 3]
    [Chemical Formula 4]
    [Chemical Formula 5]
    [Chemical Formula 6]
    [Chemical Formula 7]
    [Chemical Formula 8]
    [Chemical Formula 9]
    wherein, X2 is N or CH; Y is -O-, -S-, -C(R11R12)- or -N(R15)-; L1 represents a single bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (C2-C30)heteroarylene; Ar1 represents hydrogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C2-C30)heteroaryl; R1 through R9 independently represent hydrogen, deuterium, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, NR16R17 or SiR18R19R20; R11, R12, R15 and R16 through R20 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl or substituted or unsubstituted (C2-C30)heteroaryl, or R16 and R17 may be linked to via substituted or unsubstituted (C3-C30)alkylene or substituted or unsubstituted (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring or a monocyclic or polycyclic aromatic ring, and the carbon atom of the alicyclic ring and the monocyclic or polycyclic aromatic ring may be substituted with one or more heteroatom(s) selected from the group consisting of N, O and S.
  4. The organic electroluminescent compound of claim 3, wherein X2 represents N or CH; Y represents -O-, -S-, -C(R11R12)- or -N(R15)-;
    L1 represents a single bond or arylene selected from the following structures:
    ;
    R31 and R32 independently represent methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, pyridyl or quinolyl;
    Ar1 represents hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, terphenyl, naphthyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, fluoranthenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or N-phenylcarbazolyl, and the phenyl, biphenyl, terphenyl, naphthyl and carbazolyl of Ar1 may be further substituted with one or more substituents selected from the group consisting of deuterium, fluorine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, triphenylsilyl, trimethylsilyl, dimethylphenylsilyl, diphenylmethylsilyl, phenyl, naphthyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, phenylpyridyl, carbazolyl, fluoranthenyl, dibenzofuranyl, and dibenzothiophenyl; and
    R1 through R9 independently represent hydrogen, deuterium, phenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, amino or carbazolyl; R11, R12 and R15 independently represent hydrogen, deuterium, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, 9,9-diphenylfluorenyl, 9,9-dimethylfluorenyl, naphthyl, pyridyl, N-phenylcarbazolyl or quinolyl, and the phenyl of R11, R12 and R15 may be further substituted with one or more substituents selected from the group consisting of deuterium, halogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl and naphthyl, and R11 and R12 may be linked to each other to form a ring.
  5. The organic electroluminescent compound of claim 4, which is selected from following compounds.
  6. An organic electroluminescent device comprising the organic electroluminescent compound of any one of claims 1 to 5.
  7. The organic electroluminescent device of claim 6, which comprises a first electrode; a second electrode; and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compounds and one or more phosphorescent dopants represented by Chemical Formula 10 below.
    [Chemical Formula 10]
    M1L101L102L103
    wherein,
    M1 is selected from the group consisting of metals of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 16 of the Periodic table, and ligands L101, L102 and L103 are independently selected from the following structures:
    R201 through R203 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl or halogen;
    R204 through R219 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C1-C30)alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted mono- or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30)arylamino, SF5, substituted or unsubstituted tri(C1-C30)alkylsilyl, substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, substituted or unsubstituted tri(C6-C30)arylsilyl, cyano or halogen;
    R220 through R223 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, or (C1-C30)alkyl-substituted or unsubstituted (C6-C30)aryl;
    R224 and R225 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl or halogen, or R224 and R225 may be linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
    R226 represents substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C2-C30)heteroaryl, or halogen;
    R227 through R229 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or halogen; and
    Q represents , or ;
    R231 through R242 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30)alkyl, (C1-C30)alkoxy, halogen, substituted or unsubstituted (C6-C30)aryl, cyano or substituted or unsubstituted (C3-C30)cycloalkyl, or they 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 of claim 7, wherein the phosphorescent dopont is selected from following compounds:
  9. The organic electroluminescent device of claim 7, wherein the organic layer comprises an electroluminescent layer and a charge generating layer.
  10. The organic electroluminescent device of claim 7, wherein the organic layer further comprises one or more organic electroluminescent layers emitting red, green and blue light to emit white light.
EP11825442.4A 2010-09-17 2011-09-16 Novel organic electroluminescent compounds and organic electroluminescent device using the same Withdrawn EP2616462A4 (en)

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