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WO2011149240A2 - Composé à base de triphénylène bipolaire et élément électroluminescent organique le comprenant - Google Patents

Composé à base de triphénylène bipolaire et élément électroluminescent organique le comprenant Download PDF

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Publication number
WO2011149240A2
WO2011149240A2 PCT/KR2011/003785 KR2011003785W WO2011149240A2 WO 2011149240 A2 WO2011149240 A2 WO 2011149240A2 KR 2011003785 W KR2011003785 W KR 2011003785W WO 2011149240 A2 WO2011149240 A2 WO 2011149240A2
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formula
group
layer
same
different
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PCT/KR2011/003785
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English (en)
Korean (ko)
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WO2011149240A3 (fr
Inventor
이은정
홍진석
김신한
김경수
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Doosan Corp
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Doosan Corp
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    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • 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
    • H05B33/20—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
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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

Definitions

  • the present invention relates to a bipolar triphenylene compound and an organic electroluminescent device comprising the same.
  • organic electroluminescent (EL) devices led to blue electroluminescence using anthracene monocrystals in 1965, based on Bernanose's observation of organic thin film emission in the 1950s.
  • EL organic electroluminescent
  • an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer has been proposed, and has been developed in the form of introducing each characteristic organic material layer in the device to make a high efficiency and long life organic EL device. This led to the development of specialized materials used for this.
  • Such organic EL devices include an indium tin oxide (ITO) substrate, an anode, a hole injection layer that selectively receives holes from an anode, a hole transport layer that transfers holes, a light emitting layer that recombines holes and electrons, and selectively emits light. It consists of an electron transport layer for transferring electrons, an electron injection layer for accepting electrons from a cathode, and a cathode.
  • ITO indium tin oxide
  • the organic EL device applies electric energy so that holes are injected into the organic material layer from the anode and electrons from the cathode through each functional layer between the anode and the cathode.
  • holes are injected into the organic material layer from the anode and electrons from the cathode through each functional layer between the anode and the cathode.
  • excitons are formed, and when the excitons fall back to the ground, they are made of a light principle.
  • the material used as the organic material layer in the organic EL device may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors, depending on the light emission color.
  • a host / dopant system may be used as the light emitting material to increase the color purity and the light emission efficiency through energy transfer. The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than a host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to give high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • carbazole compounds such as CBP (4,4-dicarbazolybiphenyl) are used as phosphorescent host materials, and metal complex compounds containing heavy atoms such as Ir and Pt are widely used as phosphorescent dopant materials. have.
  • CBP which is currently used phosphorescent host material
  • T g glass transition temperature
  • the electron transporting material has been reported that organic metal complexes having relatively high stability and electron transfer speed are good candidates as organic monomolecular materials, and Alq3 having excellent stability and high electron affinity has been reported to be the best. It is used by default.
  • organic monomolecular substances having imidazole group, oxazole group, and thiazole group have been reported as conventional electron injection materials and electron transport materials.
  • metal complex compounds of these materials have already been reported to be applied to the blue light emitting layer or the cyan light emitting layer of the organic EL device.
  • An object of the present invention is to provide a bipolar triphenylene-based compound and an organic electroluminescent device comprising the same, which can improve various characteristics such as driving voltage, luminous efficiency, luminance, thermal stability and device life. It is done.
  • the present invention provides a compound represented by the following Chemical Formula 1, preferably a bipolar triphenylene-based compound:
  • R 1 and R 2 are different from each other, and each independently represent hydrogen, deuterium, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ cycloalkyl of C 40 alkynyl group, C 3 ⁇ C 40 of An alkyl group, a C 3 to C 40 heterocycloalkyl group, a C 6 to C 40 arylalkyl group, a C 1 to C 40 alkyloxy group, a C 5 to C 40 aryloxy group, a C 5 to C 40 arylamino group, Or a C 5 to C 40 diarylamino group, C 5 to C 40 aryl group, C 5 to C 40 heteroaryl group, and a substituent represented by the following formula (2); Or a group forming a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group,
  • R 1 and R 2 are each independently deuterium, halogen, nitrile group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ C 40 alkoxy group, C 1 ⁇ C Or substituted with one or more selected from the group consisting of 40 amino groups, C 3 to C 40 cycloalkyl groups, C 3 to C 40 heterocycloalkyl groups, C 6 to C 40 aryl groups and C 5 to C 40 heteroaryl groups Or unsubstituted,
  • R 1 and R 2 is a C 2 to C 40 heteroaryl group each including at least one element selected from the group consisting of N, O and S;
  • L, m, n and o are each independently an integer ranging from 1 to 5,
  • a plurality of Q 1 is the same or different from each other, a plurality of Q 2 is the same or different from each other, a plurality of Q 3 is the same or different from each other, a plurality of Q 4 is the same or different from each other,
  • Q above One , Q 2 , Q 3 And Q 4 Is are the same as or different from each other, and each independently hydrogen, deuterium, halogen, nitrile group, nitro group, C One ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl, C One ⁇ C 40 Alkoxy group, C One ⁇ C 40 Amino group, C 3 ⁇ C 40 Cycloalkyl group, C 3 ⁇ C 40 Heterocycloalkyl group, C 6 ⁇ C 40 Aryl group and C 5 ⁇ C 40 It is selected from the group consisting of a heteroaryl group of; Or a group which forms a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring with an adjacent group; Or a connector).
  • the present invention also provides an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer
  • an organic electroluminescent device characterized in that it comprises a compound represented by the formula (1).
  • the compound represented by Formula 1 may be used in at least one selected from the group consisting of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer and a light emitting layer.
  • the bipolar compound represented by Chemical Formula 1 according to the present invention is used as a material selected from the group consisting of an electron transporting material, a hole transporting material and a host material of an organic electroluminescent device, an electron donor group (EDG) in one molecule )
  • EWG electron withdrawing group
  • the bipolar compound in which the electron withdrawing group (EWG) are introduced simultaneously improve the charge balance by controlling the carrier transport, thereby improving the recombination efficiency, thereby improving the luminous efficiency, luminance and thermal stability of the organic EL device.
  • Various characteristics such as driving voltage and lifespan characteristics can be improved.
  • the compound represented by Chemical Formula 1 according to the present invention is a bipolar triphenylene-based compound, the electron donor group (EDG) and the electron withdrawing group (EWG) are simultaneously substituted with the triphenylene-based moiety (moiety), wherein the EDG and EWG is independently a C 2 ⁇ C 40 heteroaryl group containing one or more elements selected from the group consisting of N, O and S.
  • EDG electron donor group
  • EWG electron withdrawing group
  • the triphenylene-based moiety moiety
  • the EDG and EWG is independently a C 2 ⁇ C 40 heteroaryl group containing one or more elements selected from the group consisting of N, O and S.
  • the carrier is not biased to either side, and the imbalance of exciton recombination caused by the fast mobility of holes can be alleviated, so that the organic electroluminescent device has a luminous efficiency, luminance, thermal stability, driving voltage, and lifetime. Properties can be improved overall.
  • Examples of the C 2 ⁇ C 40 heteroaryl group containing one or more elements selected from the group consisting of N, O and S include a substituent represented by the following formula (3) to a heteroaryl group represented by the formula (39), This is not restrictive.
  • heteroaryl groups represented by Formula 3 to Formula 39 below heteroaryl groups represented by Formula 3 to heteroaryl groups represented by Formula 17 are EDG, and heteroaryl groups represented by Formula 18 to Formula 18 The heteroaryl group represented by 39 is EWG:
  • L, m, n, o and p are each independently integers ranging from 1 to 5;
  • a plurality of Q 1 is the same or different from each other, a plurality of Q 2 is the same or different from each other, a plurality of Q 3 is the same or different from each other, a plurality of Q 4 is the same or different from each other, a plurality of Q 5 is each other Same or different;
  • Q above One , Q 2 , Q 3 , Q 4 And Q 5 Is are the same as or different from each other, and each independently hydrogen, deuterium, halogen, nitrile group, nitro group, C One ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl, C One ⁇ C 40 Alkoxy group, C One ⁇ C 40 Amino group, C 3 ⁇ C 40 Cycloalkyl group, C 3 ⁇ C 40 Heterocycloalkyl group, C 6 ⁇ C 40 Aryl group and C 5 ⁇ C 40 It is selected from the group consisting of a heteroaryl group of; Or a group which forms a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring with an adjacent group; Or a coupler.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).
  • the present invention is an organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode, wherein At least one is characterized in that it comprises a compound represented by the formula (1).
  • the organic material layer including the compound represented by Formula 1 may be any one or more of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer and a light emitting layer.
  • the compound represented by Formula 1 may be included alone or in plurality.
  • the compound represented by Formula 1 when the compound represented by Formula 1 is included in the organic electroluminescent device as a material of the electron injection layer, the electron transport layer, the hole injection layer, the hole transport layer, the electron injection / transport ability or hole injection / of the organic electroluminescent device Transport capacity can be maximized.
  • the compound represented by Chemical Formula 1 when used as a material of the light emitting layer of the organic EL device, specifically, a host material that can be combined with a dopant, the luminous efficiency of the organic EL device and Lifespan characteristics can be improved.
  • the organic material layer other than the organic material layer containing the compound represented by Formula 1 of the present invention may be a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and / or an electron injection layer.
  • a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode may be sequentially stacked, wherein the hole injection layer, hole At least one of the transport layer, the light emitting layer, and the electron transport layer may include the compound represented by Chemical Formula 1.
  • an electron injection layer may be positioned on the electron transport layer, in which the compound represented by Formula 1 may be included in the electron injection layer.
  • the organic EL device according to the present invention may not only have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between the electrode and the organic material layer.
  • the organic material layer including the compound represented by Chemical Formula 1 may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the organic electroluminescent device according to the present invention is an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of at least one organic material layer is formed to include the compound represented by Formula 1 of the present invention. It can be prepared by forming a.
  • a silicon wafer, a quartz or glass plate, a metal plate, a plastic film or sheet may be used as the substrate.
  • the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT),
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • materials such as a hole injection layer, a hole transport layer, an electron injection layer are not particularly limited, and conventional materials known in the art may be used.
  • ITO Indium tin oxdie
  • a thin film coated glass substrate with a thickness of 1500 kPa was washed by distilled water ultrasonic. After the washing of distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried, transferred to a plasma cleaner, and the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was used with a vacuum depositor.
  • NPB N , N -di (naphthalene-) 1-yl) -N , N- diphenylbenzidine
  • ADN 9,10-di (naphthalen-2-yl) anthracene
  • DS-405 Doosan Corporation
  • a light emitting layer was formed. Thereafter, the compound represented by Formula 40 synthesized in Example 1 as an electron transporting material was deposited to a thickness of 250 kPa on the light emitting layer to form an electron transporting layer. Subsequently, 10F thick LiF was deposited on the electron transport layer to form an electron injection layer, and 2,000 nm thick Al was deposited on the electron injection layer to form a cathode.
  • Example 4 When forming the electron transport layer in Example 4, it was carried out in the same manner as in Example 4 except for using the compound represented by the formula 43 synthesized in Example 2 instead of the compound represented by the formula 40 as the electron transport material An organic light emitting device was manufactured.
  • Example 4 When forming the electron transport layer in Example 4, it was carried out in the same manner as in Example 4 except for using the compound represented by Formula 58 synthesized in Example 3 instead of the compound represented by Formula 40 as the electron transport material An organic light emitting device was manufactured.
  • An organic light-emitting device was manufactured in the same manner as in Example 4, except that Alq3 (aluminum tris (8-hydroxyquinoline)) was used instead of the compound represented by Formula 40 as the electron transporting material in the formation of the electron transporting layer. was prepared.
  • Alq3 aluminum tris (8-hydroxyquinoline)
  • the organic light emitting device (Examples 4 to 6) using the compound according to the present invention as an electron transporting material for forming an electron transporting layer is a conventional organic light emitting device using Alq3 as an electron transporting material (compared to The driving voltage and luminous efficiency were much better than Example 1), and in particular, the thermal stability was confirmed to be improved.
  • NPB N , N -di (naphthalene-1-yl) -N , N -diphenylbenzidine
  • the light emitting layer was formed by using a compound represented by Chemical Formula 40 synthesized in Example 1 as a host on the hole transport layer and doping Ir (ppy) 3 with a dopant to a thickness of 300 kPa.
  • BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline) was deposited on the emission layer to form a hole blocking layer to form a hole blocking layer, and then Alq3, which is an electron transporting material, was formed on the hole blocking layer. It was deposited to a thickness of 250 kHz to form an electron transport layer. Thereafter, LiF was deposited on the electron transport layer to a thickness of 10 kW to form an electron injection layer, and then Al was deposited to a thickness of 2,000 kW to form a cathode, thereby manufacturing an organic light emitting device.
  • Example 7 In forming the emission layer in Example 7, except for using the compound represented by Formula 43 synthesized in Example 2 instead of the compound represented by Formula 40 synthesized in Example 1 as a host material, Example 7 The organic light emitting device was manufactured by the same method as described above.
  • Example 7 when forming the emission layer in Example 7, except for using the compound represented by Formula 58 synthesized in Example 3 instead of the compound represented by Formula 40 synthesized in Example 1 as a host material,
  • the organic light emitting device was manufactured by the same method as described above.
  • Example 7 When forming the light emitting layer in Example 7, using CBP (4,4'-di (9H-carbazol-9-yl) biphenyl) instead of the compound represented by Formula 40 synthesized in Example 1 as a host material Except that, the organic light emitting device was manufactured in the same manner as in Example 7.
  • CBP 4,4'-di (9H-carbazol-9-yl) biphenyl
  • the organic light emitting device (Examples 7 to 9) using the compound according to the present invention as a host material in terms of driving voltage and luminous efficiency than the conventional organic light emitting device (Comparative Example 2) using CBP as the host material was found to be superior.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention porte sur un composé à base de triphénylène bipolaire et sur un élément électroluminescent organique le comprenant et, plus spécifiquement, le composé à base de triphénylène bipolaire peut être utilisé comme matière quelconque parmi une matière de couche d'injection d'électrons, une matière de couche de transport d'électrons, une matière de couche d'injection de trous, une matière de couche de transport de trous et une matière hôte, afin d'améliorer des propriétés telles que l'efficacité lumineuse, la luminance lumineuse, la stabilité thermique, la tension de commande et la durée de vie de l'élément électroluminescent organique.
PCT/KR2011/003785 2010-05-28 2011-05-24 Composé à base de triphénylène bipolaire et élément électroluminescent organique le comprenant Ceased WO2011149240A2 (fr)

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KR1020100050467A KR101244599B1 (ko) 2010-05-28 2010-05-28 바이폴라 트리페닐렌계 화합물 및 이를 포함하는 유기 전계 발광 소자
KR10-2010-0050467 2010-05-28

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CN112125895A (zh) * 2019-06-24 2020-12-25 北京鼎材科技有限公司 一种化合物及其应用、包含其的有机电致发光器件
US20210094914A1 (en) * 2018-06-19 2021-04-01 Lt Materials Co., Ltd. Heterocyclic compound, organic light emitting diode comprising same, manufacturing method therefor, and composition for organic layer
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