WO2010126270A1 - Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant - Google Patents

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

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WO2010126270A1
WO2010126270A1 PCT/KR2010/002629 KR2010002629W WO2010126270A1 WO 2010126270 A1 WO2010126270 A1 WO 2010126270A1 KR 2010002629 W KR2010002629 W KR 2010002629W WO 2010126270 A1 WO2010126270 A1 WO 2010126270A1
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organic electroluminescent
alkyl
fused
aryl
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Sung Jin Eum
Chi Sik Kim
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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Definitions

  • the present invention relates to novel organic electroluminescent compounds, and organic electroluminescent devices employing the same.
  • the organic electroluminescent compounds according to the invention may be contained in an electron transport layer of organic electroluminescent devices.
  • 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.
  • Organic electroluminescent materials for organic EL devices can be generally classified into electroluminescent materials and charge transport materials.
  • the electroluminescent materials are directly associated with luminescent color and luminous efficiency.
  • properties required for such electroluminescent materials include that the material should have high fluorescent 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.
  • Representatives for conventional electron transport material include aluminum complexes such as tris(8-hydroxyquinoline)aluminum (III) (Alq), which has been used prior to the multi-layered thin film OLED′s disclosed by Kodak in 1987; and beryllium complexes such as bis(10-hydroxybenzo-[ h ]quinolinato)beryllium (Bebq), which was reported in the middle of 1990′s in Japan [T. Sato et al., J. Mater. Chem . 10 (2000) 1151].
  • Alq tris(8-hydroxyquinoline)aluminum
  • Bebq beryllium complexes
  • Bebq bis(10-hydroxybenzo-[ h ]quinolinato)beryllium
  • electron transport materials of non-metal complex type having good features which have been reported up to the present include spiro -PBD[N. Jahansson et al., Adv. Mater. 10 (1998) 1136], PyPySPyPy [M. Uchida et al., Chem. Mater . 13 (2001) 2680] and TPBI [Y. T. Tao et al., Appl. Phys. Lett . 77 (2000) 1575] of Kodak.
  • spiro -PBD N. Jahansson et al., Adv. Mater. 10 (1998) 1136]
  • PyPySPyPy M. Uchida et al., Chem. Mater . 13 (2001) 2680
  • TPBI Y. T. Tao et al., Appl. Phys. Lett . 77 (2000) 1575] of Kodak.
  • the object of the invention is to overcome the problems of conventional techniques as described above, and to provide organic electroluminescent compounds comprising an excellent backbone to obtain better luminous efficiency, and improved power consumption and device life, as compared to conventional electron transport materials.
  • Another object of the invention is to provide organic electroluminescent devices employing those novel organic electroluminescent in the electron transport layer.
  • the present invention relates to organic electroluminescent compounds represented by Chemical Formula (1), and organic electroluminescent devices employing the same. Since the organic electroluminescent compounds according to the invention contained in an electron transport layer of an organic electroluminescent device lowers the operation voltage, the devices exhibiting noticeably improved luminous efficiency and reduced power consumption can be obtained.
  • the present invention provides organic electroluminescent compounds represented by Chemical Formula (1):
  • L represents 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), (C1-
  • R 1 through R 4 , Ar 1 and Ar 2 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl with or without substituent(s), (C6-C30)aryl with or without substituent(s), substituted or unsubstituted (C6-C30)aryl fused with one or more (C3-C30)cycloalkyl 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-to7-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
  • X represents O, S or NR 5 ;
  • R 5 , R 31 through R 33 and R 41 through R 48 are defined as for R 1 through R 4 , Ar 1 and Ar 2 above;
  • n an integer 1 or 2.
  • alkyl alkoxy 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 and 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
  • 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 is 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, indolo[3,2-b]carbazole; cycloalkylene such as cyclopentylene, cyclohexylene, cycloheptylene and cyclooctylene; -O- and S-, but they are not restricted thereto. Those groups may be further substituted as described for Chemical Formula (1).
  • Each group of R 1 through R 5 , R 31 through R 33 and R 41 through R 48 is independently selected from hydrogen, deutereium, halogen, alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl and octyl, aryl groups such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl and triphenylenyl, cyano, trialkylsilyl groups such as trimethylsilyl, triethylsilyl, dimethylethylsilyl and tributylsilyl, dialkylarylsilyl groups such as dimethylphenylsilyl, and triarylsilyl groups such as
  • Ar 1 and Ar 2 are independently selected from hydrogen, deuterium, halogen, alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, ethylhexyl, heptyl and octyl, aryl groups such as phenyl, naphthyl, fluorenyl, biphenyl, phenanthryl, terphenyl, pyrenyl, perylenyl, spirobifluorenyl, fluoranthenyl, chrysenyl and triphenylenyl, aryl groups fused with one or more cycloalkyl group(s) such as 1,2-dihydroacenaphthyl, heterocycloalkyl groups fused with one or more aromatic ring(s) such as benzopyrrolidino, benzopiperidino, dibenzomorpholino and dibenzoazepino; amino
  • R 31 through R 33 are defined as for R 1 through R 4 , Ar 1 and Ar 2 above;
  • R 41 through R 48 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.
  • L, Ar 1 and Ar 2 , X, R 1 through R 4 are defined as in 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 material for electron transport layer.
  • the organic layer comprises one or more layer(s) including the organic electroluminescent compound represented by Chemical Formula (1) and one or more layer(s) comprised of a fluorescent host and a fluorescent dopant, or a phosphorescent host and a phosphorescent dopant.
  • a fluorescent host, a fluorescent dopant, a phosphorescent host and a phosphorescent dopant to be applied to the organic electroluminescent devices according to the invention are not particularly restricted.
  • 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, lanthanidemetals and d-transition elements in the Periodic Table of Elements, or complex(es) thereof, as well as the organic 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
  • Examples of chalcogenides preferably include SiO x (1 ⁇ X ⁇ 2), AlO x (1 ⁇ X ⁇ 1.5), SiON, SiAlON, or thelike.
  • Examples of metal halides preferably include LiF, MgF 2 ,CaF 2 ,fluoridesofrareearthmetalorthelike.
  • 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 disclosed organic electroluminescent compound When included in an electron transport layer of an organic electroluminescent device, the disclosed organic electroluminescent compound can significantly reduce power consumption with reducing operation voltage of the device, while exhibiting improved luminous efficiency.
  • 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 to reach 10 -6 torrofvacuuminthechamber. 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 dinaphthylanthracene (DNA) as electroluminescent host material, and Compound (D) (of which the structure is shown below) was charged to another cell. Two cells were simultaneously heated with vapor-deposition rate of Compound (D) at a concentration of 2 to 5% by weight. Thus, an electroluminescent layer having the thickness of 30 nm was vapor-deposited on the hole transport layer.
  • DNA dinaphthylanthracene
  • Compound (D) of which the structure is shown below
  • Compound (3) according to the present invention was vapor-deposited as an electron transport layer with a thickness of 20 nm, and lithium quinolate (Liq) (of which the structure is shown below) was vapor-deposited as an electron injecting layer with a thickness of 1 to 2 nm. Thereafter, an Al cathode was vapor-deposited with a thickness of 150 nm by using another vacuum vapor-deposit device to manufacture an OLED.
  • Liq lithium quinolate
  • Each material employed for manufacturing an OLED was used as the electroluminescent material after purifying via vacuum sublimation at 10 -6 torr.
  • a hole transport and an electroluminescent layer After forming a hole injecting layer, a hole transport and an electroluminescent layer according to the same procedure as described in Example 1, tris(8-hydroxyquinoline)-aluminum (III) (Alq) was vapor-deposited as an electron transport layer with a thickness of 20 nm, and lithium quinolate (Liq) was vapor-deposited as an electron injecting layer with a thickness of 1 to 2 nm. Thereafter, an Al cathode was vapor-deposited with a thickness of 150 nm by using another vacuum vapor-deposit device to manufacture an OLED.
  • Alq tris(8-hydroxyquinoline)-aluminum
  • Liq lithium quinolate
  • the electroluminescent compounds developed by the present invention exhibited excellent features in terms of performances as compared to conventional material.

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Abstract

L'invention porte sur des composés électroluminescents organiques et sur des dispositifs électroluminescents organiques employant lesdits composés. Les composés électroluminescents organiques de l'invention sont des composés triazines substituées définis par la formule chimique (1). Les composés, lorsqu'ils sont utilisés dans une couche de transport d'électrons d'un dispositif électroluminescent organique, réduisent la consommation d'énergie et la tension du fonctionnement dudit dispositif.
PCT/KR2010/002629 2009-04-29 2010-04-27 Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant WO2010126270A1 (fr)

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