WO2012050347A1 - Nouveaux composés pour matériau électronique organique et dispositif électroluminescent organique les utilisant - Google Patents

Nouveaux composés pour matériau électronique organique et dispositif électroluminescent organique les utilisant Download PDF

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WO2012050347A1
WO2012050347A1 PCT/KR2011/007544 KR2011007544W WO2012050347A1 WO 2012050347 A1 WO2012050347 A1 WO 2012050347A1 KR 2011007544 W KR2011007544 W KR 2011007544W WO 2012050347 A1 WO2012050347 A1 WO 2012050347A1
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compound
alkyl
organic
heteroaryl
aryl
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PCT/KR2011/007544
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English (en)
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Hong Yoep Na
Seok Keun Yoon
Soo Yong Lee
Young Gil Kim
Hyo Jung Lee
Hee Choon Ahn
Su Hyun Lee
Soo-Jin Hwang
Hee Sook Kim
Doo-Hyeon Moon
Kyung Joo Lee
Bong Ok Kim
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Rohm And Haas Electronic Materials Korea Ltd.
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Priority to CN2011800586027A priority Critical patent/CN103249800A/zh
Priority to JP2013533764A priority patent/JP2013546171A/ja
Publication of WO2012050347A1 publication Critical patent/WO2012050347A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • 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
    • C07D403/10—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 linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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
    • 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
    • H10K85/649—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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass

Definitions

  • the present invention relates to novel compounds for an organic electronic material and an organic electroluminescent device including the same.
  • electroluminescence (EL) devices which are self-emissive display devices, are advantageous in that they provide a wide viewing angle, superior contrast and a fast response rate.
  • EL electroluminescence
  • 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].
  • Organic EL devices emit light using luminescence (phosphorescence or fluorescence) upon inactivation of excitons which result from electron-hole pairs formed by injecting charges into an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode).
  • Organic EL devices can emit polarized light at a luminance of 100 ⁇ 10,000 cd/m2 with a voltage of about 10 V, and simply adopt a fluorescent material, thereby emitting light in the blue to red spectral range.
  • Such a device may be formed on a flexible transparent substrate such as a plastic, and may also operate at a lower voltage, namely 10 V or less, compared to that of a plasma display panel or an inorganic EL display, and may consume comparatively less power and exhibit superior color.
  • electroluminescent material The most important factor in determining the performance including the luminous efficiency, life, etc., of an organic EL device is the electroluminescent material, and some requirements of the electroluminescent material include a high fluorescent quantum yield in a solid phase, high mobility of electrons and holes, slow decomposition upon vacuum deposition, and formation of a uniform and stable thin film.
  • the organic electroluminescent materials are broadly classified into high-molecular-weight materials and low-molecular-weight materials, and the low-molecular-weight materials include a metal complex compound and a pure organic electroluminescent material without a metal in terms of molecular structure.
  • Such an electroluminescent material is known to be a chelate complex such as a tris(8-quinolinolato)aluminum complex or the like, a coumarin derivative, a tetraphenylbutadiene derivative, a bisstyrylarylene derivative, an oxadiazole derivative, etc., which have been reported to be able to emit visible light ranging from blue to red.
  • RGB three electroluminescent materials have to be used.
  • the development of RGB electroluminescent materials having high efficiency and long life is important to improve the total properties of the organic EL device.
  • the electroluminescent material includes a host material and a dopant material for purposes of functionality.
  • a device that has very superior electroluminescent properties is known to have a structure in which a host is doped with a dopant to form an electroluminescent layer.
  • Recently, the development of an organic EL device having high efficiency and long life is being urgently called for.
  • a host material which functions as the solvent in a solid phase and plays a role in transferring energy should be of high purity and must have a molecular weight appropriate to enabling vacuum deposition.
  • the glass transition temperature and heat decomposition temperature should be high to ensure thermal stability, and high electrochemical stability is required to attain a long life, and the formation of an amorphous thin film should become simple, and the force of adhesion to materials of other adjacent layers must be good but interlayer migration should not occur.
  • the rate at which energy is transferred from a host molecule in an excited state to a dopant is not 100%, and the host material as well as the dopant may emit light.
  • a host material emits light in a wavelength range that is more clearly visible than does a dopant, and thus color purity is deteriorated due to unclear light emission of the host material. In practice, EL life and durability should be improved.
  • 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 a compound for an organic electronic material, which has a backbone so that it can achieve better luminous efficiency and device life with appropriate color coordinates compared to conventional materials.
  • Another object of the present invention is to provide an organic electroluminescent device having high efficiency and a long life using the compound for an organic electronic material as an electroluminescent material.
  • the compound for an organic electronic material represented by Chemical Formula 1 below, and an organic electroluminescent device including the same.
  • the compound for an organic electronic material according to the present invention may be used to manufacture an OLED device having very superior operating life and consuming less power due to improved power efficiency.
  • L 1 and L 2 independently represent a single bond, (C6-C30)arylene or (C3-C30)heteroarylene;
  • X 1 and X 2 independently represent CR 4 or N, in which both X 1 and X 2 are not CR 4 ;
  • ring A represents a monocyclic or polycyclic (C6-C30)aromatic ring
  • R 1 through R 4 independently represent hydrogen, deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C6-C30)ar(C1-C30)alkyl, (C6-C30)arylthio, mono or di(C1-C30)alkylamino, mono or di(C6-C30)arylamino, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, tri(C6-C30)arylsily
  • the arylene and heteroarylene of L 1 and L 2 , the aromatic ring of ring A, and the alkyl, cycloalkyl, heterocycloalkyl, alkenyl, alkynyl, aryl and heteroaryl of R 1 through R 4 may be independently further substituted with one or more selected from the group consisting of deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, halogen, cyano, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C6-C30)aryl, (C1-C30)alkoxy, (C6-C30)aryloxy, (C3-C30)heteroaryl, (C1-C30)alkyl-substituted (C3-C30)heteroaryl, (C6-C30)
  • 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 adamantyl with or without substituent(s) or (C7-C30)bicycloalkyl with or without substituent(s) 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 includes 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 bonds.
  • 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 a divalent heteroaryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, N-oxide or a quaternary salt.
  • Specific examples thereof include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, or the like, polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzoimidazolyl, benzothiazolyl, benzoiso
  • (C1-C30)alkyl includes (C1-C20)alkyl or (C1-C10)alkyl
  • (C6-C30)aryl includes (C6-C20)aryl or (C6-C12)aryl.
  • (C3-C30)heteroaryl includes (C3-C20)heteroaryl or (C3-C12)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.
  • L 1 and L 2 independently represent a single bond, (C6-C30)arylene or (C3-C30)heteroarylene;
  • X 1 and X 2 independently represent CR 4 or N, wherein both X 1 and X 2 are not CR 4 ;
  • ring A represents a monocyclic or polycyclic (C6-C30)aromatic ring;
  • R 1 through R 4 independently represent hydrogen, deuterium, (C6-C30)aryl or (C3-C30)heteroaryl; the arylene and heteroarylene of L 1 and L 2 , the aromatic ring of ring A, and the aryl and heteroaryl of R 1 through R 4 may be independently further substituted with one or more selected from the group consisting of deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, (C6-C30)aryl, (C3-C30)heteroaryl, (C1-C30)alkyl
  • R a and R b independently represent (C1-C7)alkyl or (C6-C12)aryl;
  • R c through R e independently represent hydrogen, deuterium, (C1-C30)alkyl, halo(C1-C30)alkyl, (C6-C30)aryl, (C3-C30)heteroaryl, (C1-C30)alkyl-substituted (C3-C30)heteroaryl, (C6-C30)aryl-substituted (C3-C30)heteroaryl, and (C6-C30)ar(C1-C30)alkyl;
  • the compound for an organic electronic material according to the present invention may be exemplified by the following compounds, which are not intended to limit the present invention.
  • the compound for an organic electronic material according to the present invention may be prepared as shown in Scheme 1 below, but is not limited thereto, and may also be prepared using known methods of organic synthesis.
  • an organic electroluminescent device 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 compounds for an organic electronic material of Chemical Formula 1.
  • the organic layer includes an electroluminescent layer, and the compound for an organic electronic material of Chemical Formula 1 is used as a host material in the electroluminescent layer.
  • the compound for an organic electronic material of Chemical Formula 1 when used as a host, one or more phosphorescent dopants may be included.
  • the phosphorescent dopant applied to the organic electroluminescent device of the present invention is not specifically limited but may be selected from among compounds represented by Chemical Formula 2 below.
  • M 1 is selected from the group consisting of Groups 7, 8, 9, 10, 11, 13, 14, 15 and 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, 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 substituted or unsubstituted di-(C1-C30)alkylamino, substituted or unsubstituted mono- or substituted or unsubstituted 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 unsub
  • 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 (C5-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 , wherein 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 (C5-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 phosphorescent dopant compound of Chemical Formula 2 may be exemplified by the following compounds, but is not limited thereto.
  • the organic electroluminescent device includes the compound for an organic electronic material of Chemical Formula 1, and may further include one or more compounds selected from the group consisting of arylamine compounds and styrylarylamine compounds.
  • arylamine compounds or the styrylarylamine compounds are illustrated in Korean Patent Publication No. 2010-0064712 or 2010-0048447, but are not limited thereto.
  • the organic layer may further comprise one or more metals selected from the group consisting of organic metals of Group 1, Group 2, 4 th period and 5 th period transition metals, lanthanide metals and d-transition elements or complex compounds, in addition to the compound for an organic electronic material of Chemical Formula 1.
  • the organic layer may comprise an electroluminescent layer and a charge generating layer.
  • the organic layer may include one or more organic electroluminescent layers including compounds emitting red, green and blue light at the same time, in addition to the above compound for an organic electronic material, in order to embody a white-emitting organic electroluminescent device.
  • the compounds emitting red, green and blue light may be exemplified by the compounds described in Korean Patent Publication No. 2010-0064712 or 2010-0048447, 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 electrodes among the pair of electrodes.
  • a metal chalcogenide (including the oxide) layer of silicon and aluminum may be placed on the anode surface of the electroluminescent medium layer, and a metal halide layer or a 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 a variety of 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 organic electroluminescent device having two or more electroluminescent layers may be manufactured by employing a reductive dopant layer as a charge generating layer.
  • compounds for an organic electronic material can be used to manufacture OLED devices having improved power efficiency as well as reduced operating voltage while exhibiting good luminous efficiency.
  • 1,4-dibromobenzene 110g(466mmol) and 1-naphthalene boronic acid 40g(233mmol) were dissolved in a mixture comprising toluene 2L, ethanol 500mL and water 500mL, and Pd(PPh 3 ) 4 13.4g(11.6mmol) and sodium carbonate 74g(698mmol) were added.
  • This mixture was stirred at 120°C 5 hours and cooled to room temperature, and the reaction was terminated with aqueous ammonium chloride 500mL.
  • the mixture was extracted with EA 3L, and the obtained organic layer was washed with distilled water 1L.
  • the organic layer was dried with anhydrous MgSO 4 , and the organic solvent was removed under reduced pressure. Subsequently, the obtained solid was separated using silica gel filtration and recrystallization, yielding Compound 1-6 (50g, 50%).
  • 2,4-dichloroquinazoline 27.1g(136mmol) and Compound 1-7 33.8g(136mmol) were dissolved in a mixture comprising toluene 800mL, ethanol 200mL and water 200mL, and Pd(PPh 3 ) 4 6.3g(5.45mmol) and sodium carbonate 43.3g(409mmol) were added.
  • This mixture was stirred at 120°C for 5 hours and cooled to room temperature, and the reaction was terminated with aqueous ammonium chloride 200mL.
  • This mixture was extracted with EA 1.5L, and the obtained organic layer was washed with distilled water 500mL.
  • the organic layer was dried with anhydrous MgSO 4 , and the organic solvent was removed under reduced pressure. Subsequently, the obtained solid was separated using silica gel filtration and recrystallization, yielding Compound 1-8 (21g, 42%).
  • Compound 2-1 (13g, 83%) was prepared by the same method as in the synthesis of Compound 1-1 in Preparation Example 1, with the exception that 9,9-dimethyl-9 H -fluoren-2-yl boronic acid 17.7g(74.3mmol) was used in lieu of 1-naphthalene boronic acid.
  • Compound 2-2 (4.2g, 36%) was prepared using Compound 2-1 13g(41.2mmol) by the same method as in the synthesis of Compound 1-2 in Preparation Example 1.
  • Compound 2-4 (2.5g, 63%) was prepared by the same method as in the synthesis of Compound 1-5 in Preparation Example 1, with the exception that Compound 2-3 4.3g(9.8mmol) was used in lieu of 1-naphthalene boronic acid.
  • Compound 2-5 (16.5g, 37%) was prepared by the same method as in the synthesis of Compound 1-6 in Preparation Example 1, with the exception that 2,4-dichloroquinazoline 33g(139mmol) was used in lieu of 1,4-dibromobenzene and 9,9-dimethyl-9 H -fluoren-2-yl boronic acid 25g(126mmol) was used in lieu of 1-naphthalene boronic acid.
  • Compound 20 (1.7g, 60%) was prepared by the same method as in the synthesis of Compound 1 in Preparation Example 1, with the exception that Compound 2-5 1.5g(4.2 mmol) was used in lieu of Compound 1-8 and Compound 2-4 2g(5.0 mmol) was used in lieu of Compound 1-5 .
  • Compound 23 (1.8g, 62%) was prepared by the same method as in the synthesis of Compound 1 in Preparation Example 1, with the exception that Compound 2-4 2g(5.0 mmol) was used in lieu of Compound 1-5 .
  • Compound 4-1 (94g, 60%) was prepared by the same method as in the synthesis of Compound 1-6 in Preparation Example 1, with the exception that 2-naphthalene boronic acid 157g(554mmol) was used in lieu of 1-naphthalene boronic acid and 1-bromo-4-iodobenzene 100g(581.7mmol) was used in lieu of 1,4-dibromobenzene.
  • Compound 4-2 (57g, 67.0%) was prepared by the same method as in the synthesis of Compound 1-7 in Preparation Example 1, with the exception that Compound 4-1 94g(332mmol) was used in lieu of Compound 1-6 .
  • Compound 4-3 (51g, 99.9%) was prepared by the same method as in the synthesis of Compound 1-8 in Preparation Example 1, with the exception that Compound 4-2 57g(230mmol) was used in lieu of Compound 1-7 .
  • Compound 7-1 (11g, 44%) was prepared by the same method as in the synthesis of Compound 5-2 in Preparation Example 5, with the exception that 11,12-dihydro-12,12-dimethylindeno[2,1-a]carbazole 15.3g(53.99mmol) was used in lieu of Compound 1-2 .
  • Compound 7-2 (5.8g, 57%) was prepared by the same method as in the synthesis of Compound 5-3 in Preparation Example 5, with the exception that Compound 7-1 11g(0.025mmol) was used in lieu of Compound 5-1 .
  • Compound 21 (3.3g, 45%) was prepared by the same method as in the synthesis of Compound 26 in Preparation Example 5, with the exception that Compound 7-2 5.1g(12.77mmol) was used in lieu of Compound 5-2 .
  • Compound 8-1 (18.4g, 45%) was prepared by the same method as in the synthesis of Compound 1-6 in Preparation Example 1, with the exception that 1,3-dibromobenzene 25g(0.14mol) was used in lieu of 1,4-dibromobenzene.
  • Compound 8-2 (10g, 63%) was prepared by the same method as in the synthesis of Compound 1-7 in Preparation Example 1, with the exception that Compound 8-1 18.4g(0.065mol) was used in lieu of Compound 1-6 .
  • Compound 8-3 (4.5g, 37%) was prepared by the same method as in the synthesis of Compound 1-8 in Preparation Example 1, with the exception that Compound 8-2 8.8g(85.48mmol) was used in lieu of Compound 1-7 .
  • Compound 13 (4.3g, 56%) was prepared by the same method as in the synthesis of Compound 1 in Preparation Example 1, with the exception that Compound 8-3 4.5g(0.012mol) was used in lieu of Compound 1-8 , and Compound 5-2 4.9g(0.014mol) was used in lieu of Compound 1-5 .
  • Compound 10 (5.7g, 9.94mmol, 73%) was prepared by the same method as in the synthesis of Compound 1 in Preparation Example 1, with the exception that Compound 9-1 5.87g(20.44mmol) was used in lieu of Compound 1-5 .
  • An OLED device was manufactured by using the electroluminescent material according to the present invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from a glass for OLED (manufactured by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
  • the ITO substrate was equipped in a substrate holder 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 was placed in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to evaporate NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • an electroluminescent layer was formed thereon as follows.
  • Compound 1 according to the present invention as a host was placed in a cell, and Ir(piq) 3 [tris(1-phenylisoquinoline)iridium(III)] 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 ⁇ 10 wt% doping taken place, and thereby the electroluminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer.
  • tris(8-hydroxyquinoline)-aluminum(III) (Alq) was vapor-deposited to a thickness of 20 nm as an electron transport layer on the electroluminescent layer.
  • lithium quinolate (Liq) was vapor-deposited to a thickness of 1 ⁇ 2 nm as an electron injection layer, and an Al cathode having a thickness of 150 nm was vapor-deposited using another vacuum vapor deposition apparatus to manufacture an OLED device.
  • Each compound used in the OLED device as the electroluminescent material was purified by vacuum sublimation at 10 -6 torr before use.
  • An OLED device was manufactured by the same method as Example 1 except that Compound 18 was used as a host material in the electroluminescent layer.
  • An OLED device was manufactured by the same method as Example 1 except that Compound 9 was used as a host material in the electroluminescent layer.
  • An OLED device was manufactured by the same method as Example 1 except that Compound 20 was used as a host material in the electroluminescent layer.
  • An OLED device was manufactured by the same method as Example 1 except that Compound 25 was used as a host material in the electroluminescent layer.
  • An OLED device was manufactured by the same method as Example 1 except that 4,4'-bis(carbazol-9-yl)biphenyl (CBP) was used as a host material in the electroluminescent layer in lieu of the compound according to the present invention, and bis(2-methyl-8-quinolinato)(p-phenylphenolate)aluminum(III) (BAlq) was used for a hole blocking layer.
  • CBP 4,4'-bis(carbazol-9-yl)biphenyl
  • BAlq bis(2-methyl-8-quinolinato)(p-phenylphenolate)aluminum(III)
  • organic electroluminescent compounds developed in the present invention showed superior electroluminescent properties compared to the conventional materials.
  • Devices using the organic electroluminescent compounds according to the present invention as a host material can exhibit superior electroluminescent properties and can reduce operating voltage to thus increase power efficiency, and thereby consumes less power.
  • compounds for an organic electronic material can be used to manufacture OLED devices having improved power efficiency as well as reduced operating voltage while exhibiting good luminous efficiency.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

L'invention concerne des nouveaux composés pour un matériau électronique organique, et un dispositif électroluminescent organique les utilisant. Le composé pour matériau électronique organique selon l'invention présentant un haut rendement de transport d'électrons, il empêche ainsi une cristallisation lors de la fabrication d'un dispositif et il facilite également la formation d'une couche, ce qui permet d'améliorer les propriétés du courant du dispositif. En conséquence, des dispositifs électroluminescents organiques (DELO) ayant un rendement énergétique amélioré ainsi qu'une tension de fonctionnement réduite peuvent être fabriqués.
PCT/KR2011/007544 2010-10-13 2011-10-11 Nouveaux composés pour matériau électronique organique et dispositif électroluminescent organique les utilisant WO2012050347A1 (fr)

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CN2011800586027A CN103249800A (zh) 2010-10-13 2011-10-11 用于有机电子材料的新化合物以及使用该化合物的有机电致发光器件
JP2013533764A JP2013546171A (ja) 2010-10-13 2011-10-11 有機電子材料のための新規化合物、およびこれを使用する有機電界発光素子

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KR20170129805A (ko) 2015-03-26 2017-11-27 도레이 카부시키가이샤 화합물, 및 이를 함유하는 전자 디바이스, 발광 소자, 광전 변환 소자 및 이미지 센서
US9837615B2 (en) 2013-06-04 2017-12-05 Idemitsu Kosan Co., Ltd. Nitrogen-containing heterocyclic derivative, organic electroluminescence element material using same, and organic electroluminescence element and electronic device using same
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US9434796B2 (en) 2010-12-21 2016-09-06 W. R. Grace & Co.-Conn. Catalyst composition with alkoxyalkyl ester internal electron donor and polymer from same
WO2012165832A1 (fr) * 2011-05-30 2012-12-06 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés pour une matière électronique organique et dispositif électroluminescent organique les utilisant
WO2012165844A1 (fr) * 2011-05-30 2012-12-06 Rohm And Haas Electronic Materials Korea Ltd. Composés inédits pour matériaux électroniques organiques et dispositif électroluminescent organique les utilisant
WO2012169821A1 (fr) * 2011-06-09 2012-12-13 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés pour une matière électronique organique et dispositif électroluminescent organique utilisant ces nouveaux composés
WO2013032284A1 (fr) * 2011-09-01 2013-03-07 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés électroluminescents organiques, et dispositif électroluminescent organique utilisant ces composés
CN102660257A (zh) * 2012-05-22 2012-09-12 南京邮电大学 吩噻嗪基喹唑啉类荧光离子探针及其应用
JP2015527347A (ja) * 2012-08-10 2015-09-17 ドゥーサン コーポレイション 新規な化合物及びこれを含む有機電界発光素子
US9905777B2 (en) 2012-08-10 2018-02-27 Doosan Corporation Compound and organic electroluminescence device comprising same
JP2015534547A (ja) * 2012-09-07 2015-12-03 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド ホスト化合物およびドーパント化合物の新規組み合わせおよびそれを含む有機エレクトロルミネセンスデバイス
WO2014088290A1 (fr) * 2012-12-04 2014-06-12 Rohm And Haas Electronic Materials Korea Ltd. Composés électroluminescents organiques et dispositif électroluminescent organique comprenant ceux-ci
JP2014183315A (ja) * 2013-03-15 2014-09-29 Dow Global Technologies Llc 電子フィルムおよびデバイス用のキナゾリン誘導化合物
JP2016526030A (ja) * 2013-05-13 2016-09-01 チェイル インダストリーズ インコーポレイテッド 有機光電子素子用化合物、これを含む有機発光素子および前記有機発光素子を含む表示装置
US9825242B2 (en) 2013-05-13 2017-11-21 Cheil Industries, Inc. Compound for organic optoelectric device, organic light-emitting diode including same, display device including organic light-emitting diode
US9837615B2 (en) 2013-06-04 2017-12-05 Idemitsu Kosan Co., Ltd. Nitrogen-containing heterocyclic derivative, organic electroluminescence element material using same, and organic electroluminescence element and electronic device using same
WO2016010380A1 (fr) 2014-07-17 2016-01-21 Rohm And Haas Electronic Materials Korea Ltd. Matériau de transport d'électrons et dispositif organique électroluminescent le comportant
US9624195B2 (en) 2014-12-24 2017-04-18 Gilead Sciences, Inc. Isoquinoline compounds
US9701677B2 (en) 2014-12-24 2017-07-11 Gilead Sciences, Inc. Fused pyrimidine compounds
US9730936B2 (en) 2014-12-24 2017-08-15 Gilead Sciences, Inc. Quinazoline compounds
US10206926B2 (en) 2014-12-24 2019-02-19 Gilead Sciences, Inc. Quinazoline compounds
US10548898B2 (en) 2014-12-24 2020-02-04 Gilead Sciences Inc. Quinazoline compounds
US11304948B2 (en) 2014-12-24 2022-04-19 Gilead Sciences, Inc. Quinazoline compounds
KR20170129805A (ko) 2015-03-26 2017-11-27 도레이 카부시키가이샤 화합물, 및 이를 함유하는 전자 디바이스, 발광 소자, 광전 변환 소자 및 이미지 센서
EP4391767A1 (fr) * 2022-12-22 2024-06-26 LG Display Co., Ltd. Diode électroluminescente organique et dispositif électroluminescent organique

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