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WO2012015265A1 - Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique à base de ces composés - Google Patents

Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique à base de ces composés Download PDF

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Publication number
WO2012015265A1
WO2012015265A1 PCT/KR2011/005584 KR2011005584W WO2012015265A1 WO 2012015265 A1 WO2012015265 A1 WO 2012015265A1 KR 2011005584 W KR2011005584 W KR 2011005584W WO 2012015265 A1 WO2012015265 A1 WO 2012015265A1
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substituted
unsubstituted
mmol
compound
organic electroluminescent
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PCT/KR2011/005584
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Soo Young Lee
Young Jun Cho
Bong Ok Kim
Sung Min Kim
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Rohm And Haas Electronic Materials Korea Ltd
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Priority to CN2011800470321A priority Critical patent/CN103298800A/zh
Priority to JP2013521715A priority patent/JP2013539205A/ja
Publication of WO2012015265A1 publication Critical patent/WO2012015265A1/fr

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Definitions

  • the present invention relates to novel organic electroluminescent compounds and an organic electroluminescent device including the same, and more particularly to novel organic electroluminescent compounds, suitable for use as a hole transport material or a hole injection material, and to an organic electroluminescent device using the same.
  • LCDs Liquid crystal displays
  • organic electroluminescent devices are recently receiving attention as a next-generation flat panel display, and thorough research into them is ongoing.
  • electroluminescent (EL) devices are advantageous as self-emissive display devices in that they provide a wide view 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 to form an electroluminescent layer [Appl. Phys. Lett. 51, 913, 1987].
  • the light emission mechanism of the organic EL device is that charges are injected into an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode) thus forming electron-hole pairs which then decay to emit light.
  • Such a device may be formed on a flexible transparent substrate such as plastic, and as well, may operate at a lower voltage (10 V or less) than a plasma display panel or an inorganic EL display, and may exhibit comparatively low power consumption and superior color.
  • the organic materials of the organic EL device are largely classified into a light-emitting material and a charge generating material.
  • the light-emitting material is directly related with emission color and luminous efficiency, and some requirements thereof include high fluorescent quantum yield in a solid phase, high mobility of electrons and holes, slow decomposition upon vacuum deposition, and forming a uniform stable thin film.
  • a hole injection and transport material includes copper phthalocyanine (CuPc), NPB, TPD, MTDATA (4,4’,4”-tris(3-methylphenylphenylamino)triphenylamine), etc.
  • CuPc copper phthalocyanine
  • NPB NPB
  • TPD TPD
  • MTDATA 4,4’,4”-tris(3-methylphenylphenylamino)triphenylamine
  • a device including such a material in the hold injection and transport layer is problematic because efficiency and lifetime are decreased. The reason for this is that when the organic EL device operates at high current, thermal stress occurs between the anode and the hole injection layer, and the lifetime of the device may be drastically shortened by such thermal stress. Also, the organic material used for the hole injection layer has very high hole mobility, thus breaking the hole-electron charge balance, thereby reducing quantum yield (cd/A).
  • the use of a compound having good thin film stability and a compound having high non-crystallinity is reported to exhibit high thin film stability.
  • the glass transition temperature (Tg) is used as an indicator of the non-crystallinity.
  • the conventional MTDATA has a Tg of 76°C, and is thus not regarded as having non-crystallinity. Such materials are unsatisfactory in terms of the durability of organic EL devices and also luminous efficiency based on hole injection and transport properties.
  • an object of the present invention is to provide an organic EL compound the backbone of which is superior in luminous efficiency and device lifetime to conventional hole injection or hole transport materials, and an organic EL device using such a novel organic EL compound as a hole injection layer or a hole transport layer.
  • an organic EL compound represented by Chemical Formula 1 below is provided in the hole injection layer or the hole transport layer of the organic EL device, thus reducing the operating voltage of the device and increasing the luminous efficiency thereof.
  • the present invention provides an organic EL compound represented by Chemical Formula 1 below.
  • X represents -O-, -S-, -C(R 11 R 12 )- or -Si(R 13 R 14 )-, wherein R 11 to R 14 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C3-C30)heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, or substituted or unsubstituted (C3-C30)cycloalkyl, or are linked to adjacent substituents to form a ring;
  • R 1 to R 4 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C3-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 cycloalkyls, 5- to 7-membered heterocycloalkyl fused with one or more substituted or unsubstituted aromatic rings or (C3-C30)cycloalkyl fused with one or more substituted or unsubstituted aromatic rings, substituted or unsubstituted (
  • R 5 and R 6 represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C3-C30)heteroaryl, or substituted or unsubstituted 5- to 7-membered heterocycloalkyl, or are linked to adjacent substituents to form a ring;
  • L 1 and L 2 independently represent a chemical bond, substituted or unsubstituted (C6-C30)arylene, or substituted or unsubstituted (C3-C30)heteroarylene, in which the case where both L 1 and L 2 are a chemical bond is excluded;
  • Ar represents substituted or unsubstituted (C6-C30)aryl, substituted or unsubstituted (C3-C30)heteroaryl except for carbazole, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30)aryl fused with one or more cycloalkyls, substituted or unsubstituted(C3-C30)heteroaryl fused with one or more substituted or unsubstituted aromatic rings, or 5- to 7-membered heterocycloalkyl fused with one or more substituted or unsubsittuted aromatic rings, or is linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;
  • a to d independently represent an integer of 0 to 4, in which when a to d are an integer of 2 or more, R 1 , R 2 , R 3 and R 4 are the same as or different from each other, and are linked to adjacent substituents to form a ring; and
  • a substituent which is further substituted with R 1 to R 4 , R 5 and R 6 , R 11 to R 14 , L 1 , L 2 and Ar, independently represents one or more selected from among deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, (C6-C30)aryl, (C6-C30)aryl-substituted or unsubstituted (C3-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 21 R 22 R 23 Si-, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazolyl, NR 24 R 25 , BR 26 R 27 , PR 28
  • alkyl and other substituents containing “alkyl” moiety include both linear and branched species.
  • cycloalkyl includes a monocyclic hydrocarbon and a polycyclic hydrocarbon such as substituted or unsubstituted adamantyl or substituted or unsubstituted (C7-C30)bicycloalkyl.
  • 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 also includes a plurality of aryls which are linked via 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 group includes a divalent aryl group wherein the heteroatoms in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt.
  • monocyclic heteroaryl such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., polycyclic heteroaryl such as benzofuryl, benzothienyl, isobenzofuryl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl,
  • the alkyl moiety of “(C1-C30)alkyl or (C6-C30)ar(C1-C30)alkyl” includes (C1-C20)alkyl, more specifically (C1-C10)alkyl.
  • the aryl moiety of “(C6-C30)aryl and (C6-C30)ar(C1-C30)alkyl” includes (C6-C20)aryl, more specifically (C6-C12)aryl.
  • (C3-C30)heteroaryl includes (C3-C20)heteroaryl, more specifically (C3-C12)heteroaryl
  • (C3-C30)cycloalkyl includes (C3-C20)cycloalkyl, more specifically (C3-C7)cycloalkyl
  • (C3-C30)alkylene or alkenylene includes (C3-C20)alkylene or alkenylene, more specifically (C3-C10)alkylene or alkenylene.
  • substituted means that an unsubstituted substituent is further substituted.
  • organic EL compound according to the present invention is selected from among compounds represented by Chemical Formulas 2 to 5 below.
  • Ar is selected from among the following structures, but is not limited thereto.
  • organic EL compound according to the present invention is exemplified by the following compounds, but the present invention is not limited thereto.
  • organic EL compound according to the present invention may be prepared as shown in, for example, Scheme 1 below, but is not limited thereto.
  • the present invention provides an organic EL device, in which the organic EL compound according to the present invention is used as a hole injection material or a hole transport material.
  • the organic EL device 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 EL compounds of Chemical Formula 1.
  • the organic EL device includes the organic EL compound of Chemical Formula 1, and may further include one or more compounds selected from among an arylamine based compound and a styrylamine based compound, and specific examples of the arylamine based compound or styrylamine based compound are illustrated in paragraph numbers ⁇ 212> to ⁇ 224> of Korean Patent Application No. 10-2008-0060393, but is not limited thereto.
  • the organic layer may further comprise one or more metals selected from among organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d-transition elements of the Periodic Table or complex compounds, in addition to the organic EL compound of Chemical Formula 1.
  • the organic layer may comprise an electroluminescent layer and a charge generating layer.
  • An organic EL device having a pixel structure of independent light-emitting mode may be embodied, wherein the organic EL device including the organic EL compound represented by Chemical Formula 1 according to the present invention is taken as a subpixel and one or more subpixels including one or more metal compounds selected from among Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag which are patterned in parallel at the same time.
  • the organic layer may include, in addition to the organic EL compound, one or more organic electroluminescent layers emitting red, green or blue light in order to embody a white-light emitting organic EL device.
  • the compound emitting red, green or blue light may be exemplified by the compounds described in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 or 10-2008-0118428, but is not limited thereto.
  • a layer selected from among a chalcogenide layer, a metal halide layer and a metal oxide layer may be disposed on the inner surface of at least one of the pair of electrodes. More specifically, a chalcogenide (including oxide) layer of silicon or aluminum may be disposed on the surface of the anode of the electroluminescent medium layer, and a metal halide layer or metal oxide layer may be disposed on the surface of the cathode of the electroluminescent medium layer, thereby attaining operating stability.
  • the chalcogenide may include, for example, SiOx (1 ⁇ x ⁇ 2), AlOx (1 ⁇ x ⁇ 1.5), SiON, SiAlON, etc.
  • the metal halide may include, for example, LiF, MgF2, CaF2, a rare-earth metal fluoride, etc.
  • the metal oxide may include, for example, Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant be disposed on the surface of at least one of the pair of electrodes thus manufactured.
  • the electron transport compound is reduced to an anion, it becomes easy to inject and transport electrons from the mixed region to the electroluminescent medium.
  • the hole transport compound is oxidized to a cation, it becomes easy to inject and transport holes from the mixed region to the electroluminescent medium.
  • 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-light emitting organic EL device having two or more electroluminescent layers may be manufactured by adopting a reductive dopant layer as a charge generating layer.
  • an organic EL compound can be used as a hole transport material or a hole injection material, so that the resultant organic EL device can exhibit good luminous efficiency and can have excellent material lifetime properties, and can be used to manufacture OLED devices having very superior operating lifetime.
  • reaction product was washed with distilled water, and extracted with ethylacetate, after which the resultant organic layer was dried with MgSO 4 , evaporated using a rotary evaporator to remove the solvent, and then purified using column chromatography, thus obtaining 6.7 g (19.8 mmol) of Compound 1-3.
  • reaction product was washed with distilled water, and extracted with ethylacetate, after which the resultant organic layer was dried with MgSO 4 , evaporated using a rotary evaporator to remove the solvent, purified using column chromatography, and then recrystallized, thus obtaining 7.3 g (10.9 mmol, 45%) of Compound 28.
  • reaction product was washed with distilled water, and extracted with ethylacetate, after which the resultant organic layer was dried with MgSO 4 , evaporated using a rotary evaporator to remove the solvent, purified using column chromatography, and then recrystallized, thus obtaining 7.0 g (9.9 mmol, 50%) of Compound 30.
  • An OLED device was manufactured using the light-emitting material according to the present invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from OLED glass (produced by Samsung-Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water in that order, and then stored in isopropanol before use.
  • an ITO substrate was equipped in a substrate folder of a vacuum deposition apparatus, and 4,4’,4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) was placed in a cell of the vacuum deposition apparatus, which was then evacuated up to 10-6 torr of vacuum in the chamber.
  • a 4,4’-N,N’-dicarbazole-biphenyl (CBP) host was placed in one cell of the vacuum deposition apparatus and a bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate ((piq) 2 Ir(acac)) dopant was placed in another cell.
  • CBP 4,4’-N,N’-dicarbazole-biphenyl
  • deposited on the electroluminescent layer was a hole blocking layer comprising bis(2-methyl-8-quinolinato)(p-phenylphenonate)aluminum (III) (BAlq) 10 nm thick, after which an electron transport layer comprising tris(8-hydroxyquinoline)-aluminum(III) (Alq) 20 nm thick was deposited.
  • a hole blocking layer comprising bis(2-methyl-8-quinolinato)(p-phenylphenonate)aluminum (III) (BAlq) 10 nm thick
  • an electron transport layer comprising tris(8-hydroxyquinoline)-aluminum(III) (Alq) 20 nm thick was deposited.
  • Liq lithium quinolate
  • Al cathode was deposited to a thickness of 150 nm using another vacuum deposition apparatus, thereby manufacturing an OLED device.
  • Each compound used in the OLED device as the light-emitting material was purified by vacuum sublimation at 10 -6 torr.
  • An OLED device was manufactured in the same manner as in Example 1, with the exception that Compound 3 according to the present invention was used as a hole transport material.
  • An OLED device was manufactured in the same manner as in Example 1, with the exception that Compound 35 according to the present invention was used as a hole transport material.
  • An OLED device was manufactured in the same manner as in Example 1, with the exception that Compound 49 according to the present invention was used as a hole transport material, and an organic iridium complex tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) was used as a dopant in the electroluminescent layer.
  • An OLED device was manufactured in the same manner as in Example 4, with the exception that Compound 58 according to the present invention was used as a hole transport material.
  • An OLED device was manufactured in the same manner as in Example 4, with the exception that Compound 4 according to the present invention was used as a hole transport material.
  • An OLED device was manufactured in the same manner as in Example 4, with the exception that Compound 61 according to the present invention was used as a hole transport material.
  • An OLED device was manufactured in the same manner as in Example 1, with the exception that Compound 42 according to the present invention was used as a hole injection material, instead of 2-TNATA (4,4’,4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine).
  • An OLED device was manufactured in the same manner as in Example 4, with the exception that Compound 45 according to the present invention was used as a hole injection material, instead of 2-TNATA (4,4’,4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine).
  • An OLED device was manufactured in the same manner as in Example 1, with the exception that Compound 46 according to the present invention was used as a hole injection material, instead of 2-TNATA (4,4’,4”-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine).
  • An OLED device was manufactured in the same manner as in Example 1, with the exception that N,N’-bis( ⁇ -naphthyl)-N,N’-diphenyl-4,4’-diamine (NPB) was used as a hole transport material in one cell of the vacuum deposition apparatus, instead of the compound according to the present invention.
  • NPB N,N’-bis( ⁇ -naphthyl)-N,N’-diphenyl-4,4’-diamine
  • An OLED device was manufactured in the same manner as in Example 4, with the exception that N,N’-bis( ⁇ -naphthyl)-N,N’-diphenyl-4,4’-diamine (NPB) was used as a hole transport material in one cell of the vacuum deposition apparatus, instead of the compound according to the present invention.
  • NPB N,N’-bis( ⁇ -naphthyl)-N,N’-diphenyl-4,4’-diamine
  • the organic EL compounds according to the present invention have superior luminous properties compared to conventional materials. Also, an organic EL device using the organic EL compound according to the present invention as a hole transport material or a hole injection material can increase the LUMO (Lowest Unoccupied Molecular Orbital) and the triplet, thus enhancing hole blocking effects, resulting in good phosphorescence efficiency and superior material lifetime properties. Furthermore, operating voltage can be decreased, and power efficiency can be increased, thereby manufacturing excellent OLED devices.
  • LUMO Large Unoccupied Molecular Orbital

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Abstract

L'invention concerne de nouveaux composés électroluminescents organiques, ainsi qu'un dispositif électroluminescent organique à base de ces composés. Le dispositif selon l'invention contient le composé électroluminescent organique comme matériau de transport de trous ou matériau d'injection de trous et présente une bonne efficacité lumineuse et une excellente durée de vie, ce qui permet de l'utiliser dans la fabrication de dispositifs à diodes électroluminescents organiques (DELO) présentant une durée de fonctionnement supérieure et consommant moins d'énergie du fait d'une efficacité énergétique accrue.
PCT/KR2011/005584 2010-07-29 2011-07-29 Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique à base de ces composés WO2012015265A1 (fr)

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