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WO2010114253A2 - Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant - Google Patents

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

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WO2010114253A2
WO2010114253A2 PCT/KR2010/001813 KR2010001813W WO2010114253A2 WO 2010114253 A2 WO2010114253 A2 WO 2010114253A2 KR 2010001813 W KR2010001813 W KR 2010001813W WO 2010114253 A2 WO2010114253 A2 WO 2010114253A2
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organic electroluminescent
alkyl
fused
aryl
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WO2010114253A3 (fr
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Young Gil Kim
Hyo Jung Lee
Young Jun Cho
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
Seung Soo Yoon
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Dow Advanced Display Materials Ltd
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Dow Advanced Display Materials Ltd
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Priority to CN2010800250539A priority Critical patent/CN102449110A/zh
Priority to JP2012503312A priority patent/JP5781499B2/ja
Publication of WO2010114253A2 publication Critical patent/WO2010114253A2/fr
Publication of WO2010114253A3 publication Critical patent/WO2010114253A3/fr
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Definitions

  • the present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices employing the same. Specifically, it relates to novel anthracene derivatives having electroluminescent properties, and organic electroluminescent devices employing the same as electroluminescent material.
  • electroluminescence (EL) devices being self-luminous type display devices, have advantages of wide visual angle, excellent contrast as well as rapid response rate.
  • Eastman Kodak firstly developed an organic EL device employing low molecular aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer, in 1987 [Appl. Phys. Lett. 51, 913, 1987].
  • An organic EL device is a device wherein, when charge is applied to an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole form a pair and then become extinct with emitting light.
  • a device can be formed on a transparent flexible substrate such as plastics. The device can be operated at a lower voltage (not more than 10 V) with relatively lower power consumption but excellent color purity, as compared to a plasma display panel or an inorganic EL display. Since the organic electroluminescent (EL) devices can develop three colors (green, blue and red), they have been focused for full colored display devices for next generation.
  • electroluminescent material The most important factor to determine luminous efficiency, lifetime or the like in an organic EL device is electroluminescent material.
  • electroluminescent materials include that the material should have high luminescent quantum yield in solid state and high mobility of electrons and holes, is not easily decomposed during vapor-deposition in vacuum, and forms uniform and stable thin film.
  • An organic EL device is composed of anode/HIL/HTL/EML/ETL/EIL/cathode.
  • the color of the light emitted (blue, green, red) from the organic electroluminescent device can be realized depending on how the electroluminescent layer (EML) is formed.
  • the electroluminescent materials are classified into host materials and dopant materials from the aspect of their functions. 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. Recently, development of organic EL devices with high efficiency and long life comes to the fore as an urgent subject, and particularly urgent is development of a material with far better EL properties as compared to conventional EL materials as considering EL properties required for a medium to large sized OLED panel.
  • a green fluorescent material As a green fluorescent material, a system wherein a coumarine derivative (Compound d, C545T), a quinacridone derivative (Compound e), DPT (Compound f) or the like is doped to Alq (a host), as a dopant, in a concentration from several % to not more than 20 % has been developed and widely used.
  • the conventional electroluminescent materials suffer from significant problem in view of lifetime with noticeable reduction of initial efficiency, though they show good performance in view of initial luminous efficiency at the level of practical use.
  • the materials have limitations to be employed for a high performance panel of larger screen.
  • the object of the invention is to overcome the problems described above, and to provide organic electroluminescent compounds comprising an excellent backbone to obtain better luminous efficiency, device life and appropriate color coordinate, as compared to conventional host materials.
  • Another object of the invention is to provide organic electroluminescent devices of high efficiency and long life by employing those organic electroluminescent compounds as electroluminescent material.
  • novel organic electroluminescent compounds were prepared according to the invention.
  • Those compounds can be employed as electroluminescent material for an organic electroluminescent device, particularly as electroluminescent host, preferably green host.
  • the compounds according to the invention provides organic electroluminescent devices with enhanced efficiency, lowered operation voltage and improved stability.
  • the present invention provides organic electroluminescent compounds represented by Chemical Formula (1):
  • L 1 and L 2 independently represent a chemical bond, (C6-C30)arylene with or without substituent(s), (C3-C30)heteroarylene with or without substituent(s), 5- to 7-membered heterocycloalkylene with or without substituent(s), substituted or unsubstituted 5- to 7-membered heterocycloalkylene fused with one or more aromatic ring(s), (C3-C30)cycloalkylene with or without substituent(s), substituted or unsubstituted (C3-C30)cycloalkylene fused with one or more aromatic ring(s), adamantylene with or without substituent(s), (C7-C30)bicycloalkylene with or without substituent(s), (C2-C30)alkenylene with or without substituent(s), (C2-C30)alkynylene with or without substituent(s), (C6-C30)ar(C1-C30)alkylene with or without substituent(s
  • R 1 through R 4 and Ar 1 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), substituted or unsubstituted 5- to 7-membered heterocycloalkyl fused with one or more aromatic ring(s), (C3-C30)cycloalkyl with or without substituent(s), substituted or unsubstituted (C3-C30)cycloalkyl fused with one or more aromatic ring(s), adamantyl with or without substituent(s), (C7-C30)bicy
  • n an integer 1 or 2.
  • alkyl and other substituents containing ‘alkyl’ moiety described herein include both linear and branched species.
  • aryl represents an organic radical derived from aromatic hydrocarbon by deleting one hydrogen atom therefrom.
  • An aryl group may be a monocyclic or a fused ring system, each ring of which suitably contains from 4 to 7, preferably from 5 or 6 cyclic atoms. Structures wherein two or more aryl groups are combined through single bond(s) are also included. Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphtacenyl, fluoranthenyl and the like, but are not restricted thereto.
  • the naphthyl may be 1-naphthyl or 2-naphthyl
  • the anthryl may be 1-anthryl, 2-anthryl or 9-anthryl
  • the fluorenyl may be any one of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • the heteroaryl may be a 5- or 6-membered monocyclic heteroaryl or a polycyclic heteroaryl which is fused with one or more benzene ring(s), and may be partially saturated.
  • the structures having one or more heteroaryl group(s) bonded through a single bond are also included.
  • the heteroaryl groups may include divalent aryl groups of which the heteroatoms are oxidized or quarternized to form N-oxides, quaternary salts, or the like.
  • Specific examples include monocyclic heteroaryl groups such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl; polycyclic heteroaryl groups such as benzofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazo
  • the alkyl groups in ‘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, (C1-C30)alkyloxycarbonyl, (C1-C30)alkylcarbonyl, (C1-C30)alkyloxycarbonyloxy, (C1-C30)alkylcarbonyloxy’ described in the present specification may have restricted carbon number from 1 to 20, or from 1 to 10.
  • the aryl groups in ‘(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, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C6-C30)arylcarbonyloxy or (C6-C30)aryloxycarbonyloxy’ may have restricted carbon number from 6 to 20, or from 6 to 12.
  • the heteroaryl groups in ‘(C3-C30)heteroaryl’ may have restricted carbon number from 4 to 20, or from 4 to 12.
  • the cycloalkyl groups in ‘(C3-C30)cycloalkyl’ may have restricted carbon number from 3 to 20, or from 3 to 7.
  • the alkenyl or alkynyl of ‘(C2-C30)alkenyl or alkynyl’ may have restricted carbon number from 2 to 20, or from 2 to 10.
  • L 1 and L 2 are independently selected from a chemical bond; arylene groups such as phenylene, naphthylene, anthracenylene, biphenylene, fluorenylene, triphenylenylene, fluoranthenylene, chrysenylene, terphenylene, phenanthrylene, pyrenylene and perylenylene; and heteroarylene groups such as pyridinylene, pyrazinylene, furylene, thienylene, selenophenylene, quinolinylene, quinoxalinylene, phenanthrolinylene, but they are not restricted thereto. Those groups may be further substituted as described for Chemical Formula (1).
  • R 51 through R 58 independently represent substituted or unsubstituted (C1-C30)alkyl, substituted or unsubstituted (C6-C30)aryl, or substituted or unsubstituted (C3-C30)heteroaryl, or each of them may be linked to an adjacent substituent via (C3-C30)alkylene or (C3-C30)alkenylene with or without a fused ring to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring.
  • organic electroluminescent compounds according to the present invention can be more specifically exemplified by the following compounds, but they are not restricted thereto.
  • R 1 through R 4 , L 1 , L 2 and Ar 1 are defined as for Chemical Formula (1).
  • the present invention also provides an organic electroluminescent device which is comprised of a first electrode; a second electrode; and at least one 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 electroluminescent compound is employed as host material of the electroluminescent layer.
  • the organic electroluminescent device according to the present invention is characterized in that the organic layer comprises an electroluminescent layer containing one or more organic electroluminescent compound(s) represented by Chemical Formula (1), as well as one or more dopant(s).
  • the dopant to be applied to an organic electroluminescent device according to the invention is not particularly restricted, but preferably selected from the compounds represented by Chemical Formula (2) or (3):
  • L represents (C6-C30)arylene with or without substituent(s), (C3-C30)heteroarylene with or without substituent(s);
  • the electroluminescent layer means the layer where electroluminescence occurs, and it may be a single layer or a multi-layer consisting of two or more layers laminated.
  • a mixture of host-dopant is used according to the constitution of the present invention, noticeable improvement in luminous efficiency due to the inventive electroluminescent host could be confirmed. This can be achieved by the doping concentration of 0.5 to 10% by weight.
  • the host according to the present invention exhibits higher hole and electron conductivity, and excellent stability of material as compared to other conventional host materials, and provides improved device life as well as luminous efficiency.
  • the dopant compounds represented by Chemical Formula (3) can be exemplified by those described in Korean Patent Application No. 10-2009-0023442. More preferably they are selected from the following structures, but not restricted thereto.
  • the organic electroluminescent device according to the present invention may further comprise one or more compound(s) selected from a group consisting of arylamine compounds and styrylarylamine compounds, in addition to the organic electroluminescent compound represented by Chemical Formula (1).
  • the arylamine or styrylarylamine compounds are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but not being restricted thereto.
  • the organic layer may further comprise one or more metal(s) selected from a group consisting of organometals of Group 1, Group 2, 4 th period and 5 th period transition metals, lanthanide metals and d-transition elements in the Periodic Table of Elements, or complex(es) thereof, as well as the electroluminescent compound represented by Chemical Formula (1).
  • the organic layer may comprise an electroluminescent layer and a charge generating layer at the same time.
  • the organic electroluminescent device may also comprise one or more organic electroluminescent layer(s) emitting blue, green or red light, in addition to the organic electroluminescent compound(s) represented by Chemical Formula (1), to form an organic electroluminescent device emitting white light.
  • the compounds emitting blue, green or red light are exemplified by Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but not being restricted thereto.
  • an organic electroluminescent device it is preferable to arrange one or more layer(s) (here-in-below, referred to as the ‘surface layer’) selected from chalcogenide layers, metal halide layers and metal oxide layers, on the inner surface of at least one side of the pair of electrodes.
  • the surface layer selected from chalcogenide layers, metal halide layers and metal oxide layers.
  • a chalcogenide layer of silicon and aluminum metal (including oxides) on the anode surface of the EL medium layer, and a metal halide layer or a metal oxide layer on the cathode surface of the EL medium layer.
  • Examples of metal halides preferably include LiF, MgF 2 , CaF 2 , fluorides of rare earth metal or the like.
  • Examples of metal oxides preferably include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, or the like.
  • 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 electron transport compound and a reductive dopant, or a mixed region of a hole transport compound with an oxidative dopant. Accordingly, the electron transport compound is reduced to an anion, so that injection and transportation of electrons from the mixed region to an EL medium are facilitated. In addition, since the hole transport compound is oxidized to form a cation, injection and transportation of holes from the mixed region to an EL 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.
  • a white electroluminescent device having two or more electroluminescent layers can be manufactured by employing a reductive dopant layer as a charge generating layer.
  • the organic electroluminescent compounds according to the present invention exhibit high luminous efficiency and excellent life property of the material, so that OLED’s having very good operation life can be manufactured therefrom.
  • OLED devices were manufactured by using the electroluminescent material according to the invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) prepared from 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-deposit device, and 4,4′4′′-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA)(of which the chemical structure is shown below) was placed in a cell of the vacuum vapor-deposit device, which was then ventilated up to 10 -6 torr of vacuum in the chamber. Electric current was applied to the cell to evaporate 2-TNATA, thereby providing vapor-deposit of a hole injection layer having 60 nm of thickness on the ITO substrate.
  • 2-TNATA 4,4′4′′-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine
  • NPB N,N′-bis( ⁇ -naphthyl)-N,N′-diphenyl-4,4′-diamine
  • an electroluminescent layer was vapor-deposited thereon as follows. To one cell of a vacuum vapor-deposit device, charged was Compound (1) according to the present invention as host, and Compound (A) was charged to another cell as dopant. Two substances were evaporated at different rates to provide doping at a concentration of 2 to 5% by weight on the basis of the host. Thus, an electroluminescent layer having the thickness of 30 nm was vapor-deposited on the hole transport layer.
  • Each material employed for manufacturing an OLED was used as the electroluminescent material after purifying via vacuum sublimation at 10 -6 torr.
  • an electron transport layer and an electron injecting layer were vapor-deposited according to the same procedures as in Example 1, and Al cathode was vapor-deposited by using another vacuum vapor-deposit device with a thickness of 150 nm, to manufacture an OLED.
  • an electron transport layer and an electron injecting layer were vapor-deposited according to the same procedures as in Example 1, and Al cathode was vapor-deposited by using another vacuum vapor-deposit device with a thickness of 150 nm, to manufacture an OLED.

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

Abstract

L'invention porte sur de nouveaux composés organiques électroluminescents et sur des dispositifs organiques électroluminescents les comprenant. Avec un bon rendement lumineux et d'excellentes propriétés de pureté de couleur et de durée de vie, les composés organiques électroluminescents selon l'invention peuvent être utilisés pour fabriquer des dispositifs organiques à diode électroluminescente (DELO) ayant une très bonne durée de fonctionnement.
PCT/KR2010/001813 2009-03-31 2010-03-24 Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les utilisant Ceased WO2010114253A2 (fr)

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US10388885B2 (en) 2012-11-02 2019-08-20 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
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