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WO2011055914A1 - Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant - Google Patents

Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant Download PDF

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Publication number
WO2011055914A1
WO2011055914A1 PCT/KR2010/006920 KR2010006920W WO2011055914A1 WO 2011055914 A1 WO2011055914 A1 WO 2011055914A1 KR 2010006920 W KR2010006920 W KR 2010006920W WO 2011055914 A1 WO2011055914 A1 WO 2011055914A1
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substituent
alkyl
aryl
organic electroluminescent
heteroaryl
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PCT/KR2010/006920
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English (en)
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Chi Sik Kim
Young Jun Cho
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Publication of WO2011055914A1 publication Critical patent/WO2011055914A1/fr

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    • 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
    • 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
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/658—Organoboranes
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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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
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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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
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    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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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
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms

Definitions

  • the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device using the same. More particularly, the organic electroluminescent compound is represented by Chemical Formula 1:
  • electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices.
  • Eastman Kodak first developed an organic EL device using a low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [ Appl. Phys. Lett. 51, 913, 1987].
  • an organic EL device when a charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole are paired and exciton is generated. Light is emitted by using electroluminescence (phosphorescence or fluorescence) in a state that the exciton is inactivated.
  • the organic EL device emits polarization of light at voltage of about 10V and high brightness of about 100 ⁇ 10,000cd/m2.
  • the organic EL device has a feature in that light is emitted in a spectrum ranging from blue color to red color by simply selecting a fluorescent material.
  • the organic EL device is advantageous in that it can be formed on a flexible transparent substrate such as plastic, is operable with relatively low voltage (10 V or lower) as compared to plasma display panels or inorganic EL displays, consumes less power, and provides excellent color.
  • the electroluminescent material In an organic EL device, the most important factor that determines its performance including luminescence efficiency and operation life is the electroluminescent material. Some requirements of the electroluminescent material include high electroluminescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
  • Organic electroluminescent materials are generally classified into high-molecular materials and low-molecular materials.
  • the low-molecular materials include metal complexes and thoroughly organic electroluminescent materials which do not contain metal, from the aspect of molecular structure.
  • Such electroluminescent materials include chelate complexes such as tris(8-quinolinolato)aluminum complexes, coumarin derivatives, tetraphenylbutadiene derivatives, bis(styrylarylene) derivatives and oxadiazole derivatives. From those materials, it is reported that light emission of visible region from blue to red can be obtained.
  • electroluminescent materials for red, green and blue
  • OLED organic light-emitting diode
  • the important issue is to develop red, green and blue electroluminescent materials with high efficiency and long life, in order to enhance the overall feature of the organic electroluminescent (EL) devices.
  • the EL materials are classified into host materials and dopant materials. It is generally known that a device structure having the most excellent EL properties can be fabricated with an EL layer prepared by doping a dopant to a host.
  • the desired properties for the host material are high purity and appropriate molecular weight to enable vapor-deposition in vacuo.
  • glass transition temperature and thermal decomposition temperature should be high enough to ensure thermal stability.
  • the host material should have high electrochemical stability for providing long life. It is to be easy to form an amorphous thin film, with high adhesiveness to other adjacent materials but without interlayer migration.
  • the organic EL device When the organic EL device is fabricated by doping technology, transferring energy from host molecule to dopant in an excited state does not achieve 100% and a host material as well as dopant emits light. In particular, since the host material emits light in a range of wavelength having larger visibility than the dopant in case of a red light emitting device, color purity is deteriorated due to dull light emission of the host material. If the technology is actually applied, it is required to increase luminescence life and improve durability.
  • 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.
  • the OLED devices do not have satisfactory operation life. Therefore, development of more stable, higher-performance host materials is required.
  • an object of the present invention is to provide an organic electroluminescent compound having luminescence efficiency and device operation life improved over existing materials and having superior backbone with appropriate color coordinates in order to solve the aforesaid problems.
  • Another object of the present invention is to provide a highly efficient and long life organic electroluminescent device employing the organic electroluminescent compound as an electroluminescent material.
  • organic electroluminescent compound represented by following Chemical Formula 1 and an organic electroluminescent device using the same. Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent life property compared to the existing host material, it may be used to manufacture OLED devices having very superior operation life and consuming less power due to improved power efficiency.
  • a 1 through A 5 independently represent CR or N;
  • L 1 represents (C6-C30)arylene with or without substituent(s) or (C3-C30)heteroarylene with or without substituent(s);
  • R, R 1 and R 2 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl(s) with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), 5- to 7-membered heterocycloalkyl with or without substituent(s), 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C3-C30)cycloalkyl fused with one or more aromatic ring(s) with or without substituent(s), cyano, nitro, NR 11 R 12 , BR 13 R 14 , PR 15 R 16 ,
  • R 31 through R 33 and R 41 through R 48 are the same as R;
  • n an integer from 0 to 5;
  • n an integer 0, 1 or 2.
  • each of R 33 and R 41 through R 48 independently represents (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s), or the R 41 through R 48 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, a mono- or polycyclic aromatic ring or a mono- or polycyclic heteroaromatic ring.
  • alkyl alkoxy and other substituents containing “alkyl” moiety include both linear and branched species and "cycloalkyl” includes monocyclic hydrocarbons as well as polycyclic hydrocarbons such as adamantyl or (C7-C30)bicycloalkyl with or without substituent(s).
  • aryl means an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen atom, and may include a 4- to 7-membered, particularly 5- or 6-membered, single ring or fused ring, including a plurality of aryls linked by single bond(s).
  • Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
  • the naphthyl includes 1-naphthyl and 2-naphthyl
  • the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl
  • the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • the heteroaryl includes more than one heteroaryls linked by single bond(s).
  • the heteroaryl group includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt.
  • monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, 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 alkyl moiety of "(C1-C30)alkyl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C1-C30)alkyloxy, (C1-C30)alkylthio", or the like may have 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms.
  • the aryl moiety of "(C6-C30)aryl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsilyl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)aryloxy, (C6-C30)arylthio", or the like may have 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms.
  • the heteroaryl of "(C3-C30)heteroaryl” may have 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms.
  • the cycloalkyl of "(C3-C30)cycloalkyl” may have 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms.
  • the alkenyl or alkynyl of "(C2-C30)alkenyl or alkynyl” may have 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
  • each substituent of the L 1 , R, R 1 , R 2 , R 11 through R 22 , R 31 through R 33 and R 41 through R 48 may be independently substituted with one or more substituent(s) selected from the group consisting of deuterium, halogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6-C30)aryl substituent(s), 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused with one or more aromatic ring(s), R a R b R c Si-[wherein R a
  • R 1 and R 2 independently represent (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s), in , R 1 and R 2 may be linked via alkylene or alkenylene with or without substituent(s) to form [wherein R 51 and R 52 independently represent hydrogen, (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)].
  • The is selected from the following structures but is not limited thereto.
  • R represents (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C3-C30)heteroaryl with or without substituent(s), R 22 X- [wherein X represents S or O, and R 22 represents (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or (C3-C30)heteroaryl with or without substituent(s)], or , and W and R 31 through R 33 are the same as defined in Chemical Formula 1, and R may be identical or different.
  • L 1 represents phenylene, naphthylene, anthracenylene, fluorenylene, phenanthrylene, biphenylene, triphenylene, fluoranthenylene, chrysenylene, pyrenylene, perylenylene, pyridinylene, furylene, thiophenylene, selenophenylene, pyridinylene, pyrazinylene, pyridazinylene, quinolinylene or quinoxalinylene; and
  • R, R 1 and R 2 independently represent hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, trifluoromethyl, phenyl, phenyloxy, phenylthio, 1-naphthyl, 2-naphthyl, biphenyl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, N-carbazolyl, N-phenyl-1-carbazolyl, N-phenyl-2-carbazolyl, N-phenyl-3-carbazolyl, N-phenyl-4-carbazolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-quinoly
  • organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but are not limited thereto:
  • organic electroluminescent compound according to the present invention may be prepared by Scheme 1, without being limited thereto:
  • a 1 through A 5 , L 1 , R 1 , R 2 and n are the same as defined in Chemical Formula 1.
  • an organic electroluminescent device which comprises a first electrode; a second electrode; and one or more organic layer(s) interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more organic electroluminescent compound(s) represented by Chemical Formula 1.
  • the organic layer may include one or more organic electroluminescent compounds of Chemical Formula 1 as an electroluminescent host and may include one or more dopant(s).
  • the dopant used in the organic electroluminescent device of the present invention is not particularly limited, but may be selected from the compounds represented by Chemical Formula 2:
  • M 1 is selected from the group consisting of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and Group 16 metals;
  • ligands L 101 , L 102 and L 103 are independently selected from the following structures:
  • R 201 through R 203 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C6-C30)aryl with or without (C1-C30)alkyl substituent(s) or halogen;
  • R 204 through R 219 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C1-C30)alkoxy with or without substituent(s), (C3-C30)cycloalkyl with or without substituent(s), (C2-C30)alkenyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), mono- or di-(C1-C30)alkylamino with or without substituent(s), mono- or di-(C6-C30)arylamino with or without substituent(s), SF 5 , tri(C1-C30)alkylsilyl with or without substituent(s), di(C1-C30)alkyl(C6-C30)arylsilyl with or without substituent(s), tri(C6-C30)arylsilyl with or without substituent(s), cyano or halogen;
  • R 220 through R 223 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s) or (C6-C30)aryl with or without (C1-C30)alkyl substituent(s);
  • R 224 and R 225 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or halogen, or R 224 and R 225 may be linked via (C3-C12)alkylene or (C3-C12)alkenylene with or without a fused ring to form an alicyclic ring or a mono- or polycyclic aromatic ring;
  • R 226 represents (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), (C5-C30)heteroaryl with or without substituent(s) or halogen;
  • R 227 through R 229 independently represent hydrogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s) or halogen;
  • Q represents , or , wherein R 231 through R 242 independently represent hydrogen, (C1-C30)alkyl with or without halogen substituent(s), (C1-C30)alkoxy, halogen, (C6-C30)aryl with or without substituent(s), cyano or (C5-C30)cycloalkyl with or without substituent(s), each of them may be linked to an adjacent substituent via alkylene or alkenylene to form a spiro ring or a fused ring, or may be linked to R 207 or R 208 via alkylene or alkenylene to form a saturated or unsaturated fused ring.
  • the dopant compound represented by Chemical Formula 2 may be exemplified by the following compounds, but are not limited thereto:
  • the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more compound(s) selected from the group consisting of arylamine compounds and styrylarylamine compounds, at the same time.
  • the arylamine compounds or styrylarylamine compounds are exemplified in Korean Patent Application No. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • the organic layer may further include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, one or more metal(s) selected from the group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements or complex compounds.
  • 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, one or more organic electroluminescent layer(s) emitting blue, green or red light at the same time in order to embody a white-emitting organic electroluminescent device.
  • the compound emitting blue, green or red light may be exemplified by the compounds described in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but are not limited thereto.
  • a layer (hereinafter referred to as "surface layer" selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on the inner surface of one or both electrode(s) among the pair of electrodes. More specifically, a 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. An operation stability may be attained therefrom.
  • the metal halide may be, for example, LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.
  • the metal oxide may be, for example, Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • an organic electroluminescent device it is also preferable to arrange on at least one surface of the pair of electrodes thus manufactured a mixed region of an electron transport compound and a reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant.
  • a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant.
  • the electron transport compound is reduced to an anion, injection and transport of electrons from the mixed region to an electroluminescent medium are facilitated.
  • the hole transport compound is oxidized to a cation, injection and transport of holes from the mixed region to an electroluminescent medium are facilitated.
  • Preferable oxidative dopants include various Lewis acids and acceptor compounds.
  • Preferable reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. Further, a white-emitting electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
  • the organic electroluminescent compound Since the organic electroluminescent compound exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLED devices having superior operation life and consuming less power due to improved power efficiency.
  • 1,4-dibromobenzene (10.5g, 44.74mmol) was dissolved in THF (150ml) and n-buLi (17.89ml, 44.74mmol, 2.5M in Hexane) was slowly added thereto at -78°C. 1 hour later, dimesitylboron fluoride (10g) was dissolved in THF (50ml). After stirring the mixture for 10 hours, distilled water was added and a product was extracted with EA. Drying with magnesium sulfate and distillation under reduced pressure followed by column separation gave a compound 1-1 (12g, 29.61mmol, 79.44%).
  • the compound 1-1 (12g, 29.61mmol) was dissolved in THF (100ml) and n-buLi (14.21ml, 35.53mmol, 2.5M in Hexane) was slowly added at -78°C. 1 hour later, trimethylborate (4.95ml, 44.42mmol) was added thereto and stirred for 10 hours. Distilled water was added and a product was extracted with EA. Drying with magnesium sulfate and distillation under reduced pressure followed by column separation gave a compound 1-2 (7g, 18.91mmol, 63.87%).
  • 2,2'-dibromobiphenyl (15g, 48.07mmol) was dissolved in ethyl ether (500ml) and n-buLi (38.4ml, 96.15mmol, 2.5M in hexane) was slowly added at 0°C. The mixture was stirred for 2 hours and an organic solvent was distilled under reduced pressure. A solid was washed with hexane and mixed with hexane (400ml). The mixture was stirred and boron trichloride 48ml (48.07mmol, 1.0M in hexane) was slowly added thereto at 0°C. The mixture was stirred for 12 hours. The produced solid was filtered under reduced pressure and washed with hexane to give a compound 2-1 (3g, 15.11mmol, 31.46%).
  • a compound 2-3 (2.3g, 8.10mmol, 64.65%) was given by combining the compound 2-2 (4g, 12.53mmol) according to the same method as preparation of the compound 1-2 in Preparation Example 1.
  • Organic electroluminescent Compounds 1 to 44 were prepared according to Preparation Examples 1 and 2.
  • Table 1 shows 1 H NMR and MS/FAB of the prepared organic electroluminescent compounds.
  • An OLED device was manufactured using the electroluminescent material according to the present invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from a glass for OLED (produced by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
  • an ITO substrate was equipped in a substrate folder of a vacuum vapor deposition apparatus, and 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum vapor deposition apparatus, which was then ventilated up to 10 -6 torr of vacuum in the chamber. Then, electric current was applied to the cell to evaporate 2-TNATA, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • 2-TNATA 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
  • N , N '-bis( ⁇ -naphthyl)- N , N '-diphenyl-4,4'-diamine (NPB) was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • an electroluminescent layer was formed thereon as follows. A compound 9 was placed in a cell of a vacuum vapor deposition apparatus as host, and a compound Ir(ppy) 3 [tris(2-phenylpyridine)iridium] was placed in another cell as a dopant. The two materials were evaporated at different rates such that an electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer at 4 to 10 wt%.
  • An OLED device was manufactured according to the same method as Example 1 except that a compound 11 according to the present invention was used on the electroluminescent layer as a host.
  • An OLED device was manufactured in the same manner as Examples 1 and 2 except that 4,4'-bis(carbazol-9-yl)biphenyl (CBP) instead of the compounds of the present invention was used as a host material in a cell of the vacuum vapor deposition apparatus and Bis(2-methyl-8-quinolinato)( p -phenyl-phenolato)aluminum(III) (BAlq) was used as the hole blocking layer.
  • CBP 4,4'-bis(carbazol-9-yl)biphenyl
  • BAlq Bis(2-methyl-8-quinolinato)( p -phenyl-phenolato)aluminum(III)
  • the organic electroluminescent compounds according to the present invention have excellent properties compared with the conventional material.
  • the device using the organic electroluminescent compound according to the present invention as a host material for light emitting has excellent electroluminescent properties and drops driving voltage, thereby increasing power efficiency and reducing power consumption.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne des composés électroluminescents organiques de formule chimique 1 : dans laquelle les variables A1, A2, A3, A4, A5, (L1)n, R1 et R2 sont telles que définies dans la description. Ces composés présentent une grande efficacité lumineuse et une excellente durée de vie du matériau et sont utilisés dans des dispositifs électroluminescents organiques. Une OLED ayant une très bonne durée de vie et une consommation énergétique améliorée est fabriquée en utilisant ces composés.
PCT/KR2010/006920 2009-11-04 2010-10-11 Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant WO2011055914A1 (fr)

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WO2012173030A1 (fr) * 2011-06-16 2012-12-20 住友化学株式会社 Élément de conversion photoélectrique
WO2013032297A1 (fr) * 2011-09-01 2013-03-07 Rohm And Haas Electronic Materials Korea Ltd. Composés benzocarbazoles et dispositifs électroluminescents les impliquant
CN103889975A (zh) * 2011-09-01 2014-06-25 罗门哈斯电子材料韩国有限公司 苯并咔唑化合物和包含它们的电致发光器件
JP2018118981A (ja) * 2011-10-06 2018-08-02 株式会社半導体エネルギー研究所 有機化合物
JP2020007323A (ja) * 2011-10-06 2020-01-16 株式会社半導体エネルギー研究所 有機化合物
WO2014015931A1 (fr) 2012-07-23 2014-01-30 Merck Patent Gmbh Matériaux destinés à des dispositifs électroluminescents organiques
JP2015530363A (ja) * 2012-07-23 2015-10-15 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子のための材料
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US12022732B2 (en) 2012-07-23 2024-06-25 Merck Patent Gmbh Materials for organic electroluminescent devices
CN103483365A (zh) * 2013-09-03 2014-01-01 太仓碧奇新材料研发有限公司 一种并三噻吩硼烷晶体管材料及其制备方法
CN103483365B (zh) * 2013-09-03 2016-04-27 太仓碧奇新材料研发有限公司 一种并三噻吩硼烷晶体管材料及其制备方法

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