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WO2010110553A2 - 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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Publication number
WO2010110553A2
WO2010110553A2 PCT/KR2010/001691 KR2010001691W WO2010110553A2 WO 2010110553 A2 WO2010110553 A2 WO 2010110553A2 KR 2010001691 W KR2010001691 W KR 2010001691W WO 2010110553 A2 WO2010110553 A2 WO 2010110553A2
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WO
WIPO (PCT)
Prior art keywords
substituent
organic electroluminescent
ring
alkyl
aryl
Prior art date
Application number
PCT/KR2010/001691
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English (en)
Other versions
WO2010110553A3 (fr
Inventor
Young Gil Kim
Young Jun Cho
Hyuck Joo Kwon
Bong Ok Kim
Sung Min Kim
Seung Soo Yoon
Original Assignee
Dow Advanced Display Materials, Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Dow Advanced Display Materials, Ltd. filed Critical Dow Advanced Display Materials, Ltd.
Priority to JP2012501926A priority Critical patent/JP5778127B2/ja
Priority to CN2010800212132A priority patent/CN102449106A/zh
Publication of WO2010110553A2 publication Critical patent/WO2010110553A2/fr
Publication of WO2010110553A3 publication Critical patent/WO2010110553A3/fr

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Classifications

    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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]
    • H10K50/14—Carrier transporting layers
    • 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]
    • H10K50/17—Carrier injection 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
    • H10K85/30—Coordination compounds
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium

Definitions

  • the present invention relates to a novel organic electroluminescent compound and an organic electroluminescent device including the same.
  • the organic electroluminescent compound according to the present invention may be included in a hole transport layer or a hole injection layer of an organic electroluminescent device.
  • electroluminescent (EL) devices are advantageous in that they provide wide view angle, superior contrast and fast response rate as self-emissive display devices.
  • Eastman Kodak first developed an organic EL device using low-molecular-weight aromatic diamine and aluminum complex as a substance for forming an electroluminescent layer [Appl. Phys. Lett. 51, 913, 1987].
  • an organic EL device when a charge is applied to an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), an electron and a hole are paired and emit light as the electron-hole pair is extinguished.
  • the organic EL device is advantageous in that it can be formed on a flexible transparent substrate such as plastic, is operable with relatively low voltage (10 V or lower) as compared to plasma display panels or inorganic EL displays, consumes less power and provides excellent color.
  • the organic materials used in an organic EL device may be classified into an electroluminescent material and a charge transport material.
  • the electroluminescent material is directly related with emitted color and luminous efficiency. Some requirements include high fluorescence quantum yield in solid state, high electron and hole mobility, resistance to decomposition during vacuum deposition, ability to form uniform film and stability.
  • the hole injection/transport material may include copper phthalocyanine (CuPc),
  • TPD N,N'-diphenyl-N,N'-bis(3-methylphenyl)-(l,r-biphenyl)-4,4'-diamine
  • MTDATA 4,4',4"-tris(3-methylphenylphenylamino)triphenylamine
  • a device using these materials in the hole injection or transfer layer is problematic in efficiency and operation life. It is because, when an organic EL device is driven under high current, thermal stress occurs between an anode and the hole injection layer. The thermal stress significantly reduces the operation life of the device. Further, since the organic material used in the hole injection layer has very high hole mobility, the hole- electron charge balance may be broken and quantum yield (cd/A) may decrease.
  • Glass transition temperature (T g ) may be a measure of the amorphousness.
  • [8] MTDATA has a glass transition temperature of 76 0 C and cannot be said to have high amorphousness. These materials are not satisfactory in the durability of the organic EL device, as well as in the luminous efficiency, which is determined by the hole injection/transport properties. Disclosure of Invention Technical Problem
  • an object of the present invention is to provide an organic electroluminescent compound providing superior luminous efficiency and device operation life as compared to existing hole injection and hole transport materials.
  • Another object of the present invention is to provide an organic electroluminescent device employing the novel organic electroluminescent compound in a hole injection layer or a hole transport layer.
  • the present invention provides an organic electroluminescent compound represented by Chemical Formula 1 and an organic electroluminescent device comprising the same.
  • the organic electroluminescent compound according to the present invention may improve luminous efficiency while lowering driving voltage of the device.
  • ring A and ring B independently represent a monocyclic or poly cyclic aromatic ring, a monocyclic or polycyclic hetero aromatic ring, a 5- or 6-membered hetero aromatic ring fused with an aromatic ring or a monocyclic or polycyclic aromatic ring fused with a 5- or 6-membered hetero aromatic ring, excluding the case where the ring A and the ring B are monocyclic aromatic rings at the same time and the substituents R 4 and R 5 are independently hydrogen, (Cl-C60)alkyl, (Cl-C60)alkoxy or (C6-C60)aryl;
  • Li represents (C6-C60)arylene with or without substituent(s), (C3-C60)heteroarylene with or without substituent(s), (C3-C60)alkenylene with or without substituent(s) or (C3-C60)alkynylene with or without substituent(s);
  • Ari represents (Cl-C60)alkyl with or without substituent(s), (C6-C60)aryl with or without substituent(s), (C3-C60)heteroaryl with or without substituent(s), heterocy- cloalkyl with or without substituent(s), (C3-C60)cycloalkyl with or without substituents), adamantyl with or without substituent(s), (C7-C60)bicycloalkyl with or without substituent(s), (C3-C60)alkenyl with or without substituent(s) or (C3-C60)alkynyl with or without substituent(s);
  • R 1 , R 2 , R 3 , R 4 R 5 R 6 and R 7 independently represent hydrogen, deuterium, halogen,
  • R 31 through R 38 independently represent (Cl-C60)alkyl, (C3-C60)cycloalkyl,
  • (C6-C60)aryl or (C3-C60)heteroaryl may be linked to an adjacent substituent via (C3-C60)alkylene or (C3-C60)alkenylene with or without a fused ring to form a fused ring, and the alkyl, cycloalkyl, aryl or heteroaryl of R 31 through R 38 may be further substituted by one or more substituent(s) selected from a group consisting of hydrogen, deuterium, halogen, (Cl-C60)alkyl, halo(Cl-C60)alkyl, (C6-C60)aryl, (C3-C60)heteroaryl with or without (C6-C60)aryl substituent, cyano, carboxyl, nitro and hydroxyl.
  • substituent(s) selected from a group consisting of hydrogen, deuterium, halogen, (Cl-C60)alkyl, halo(Cl-C60)alky
  • alkyl includes a linear or branched saturated primary hydrocarbon radical consisting only of carbon and hydrogen atoms or a combination thereof
  • alkyloxy and alkylthio respectively mean -O-alkyl and -S-alkyl, where the alkyl is the same as defined above.
  • 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, including a plurality of aryls linked by chemical bond(s).
  • Specific examples include phenyl, naphthyl, biphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc., but are not limited thereto.
  • heteroaryl means an aryl group containing 1 to 4 heteroatom(s) selected from nitrogen (N), oxygen (O), sulfur (S), phosphorus (P) and silicon (Si) as aromatic ring backbone atom(s), other remaining aromatic ring backbone atoms being carbon. It may be 5- or 6-membered monocyclic heteroaryl or polycyclic heteroaryl resulting from condensation with a benzene ring, and may be partially saturated. Further, the heteroaryl includes more than one heteroaryls linked by chemical bond(s).
  • the heteroaryl includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, N- oxide or quaternary salt.
  • Specific examples 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, etc., poly cyclic heteroaryl such as ben- zofuranyl, benzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, ben-
  • the substituents including "(Cl-C60)alkyl” may have 1 to 60 carbon atoms, specifically 1 to 20 carbon atoms, more specifically 1 to 10 carbon atoms.
  • the substituents including "(C6-C60)aryl” may have 6 to 60 carbon atoms, specifically 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms.
  • the substituents including "(C3-C60)heteroaryl” may have 3 to 60 carbon atoms, specifically 4 to 20 carbon atoms, more specifically 4 to 12 carbon atoms.
  • the substituents including "(C3-C60)cycloalkyl” may have 3 to 60 carbon atoms, specifically 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms.
  • the substituents including "(C2-C60)alkenyl or alkynyl” may have 2 to 60 carbon atoms, specifically 2 to 20 carbon atoms, more specifically 2 to 10 carbon atoms.
  • the organic electroluminescent compound of the present invention includes the compounds represented by Chemical Formulas 2 to 5:
  • ring A, ring B, L 1 , Ar 1 and R 1 through R 7 are the same as defined in Chemical Formula 1.
  • the ring A and the ring B may be independently benzene, naphthalene, anthracene, pyridine, quinoline, isoquinoline or quinoxaline, but are not limited thereto.
  • R 4 and R 5 substituted at the ring A and the ring B are not independently hydrogen, (Cl-C60)alkyl, (Cl-C60)alkoxy or (C6-C60)aryl.
  • R 3 and R 51 may be independently methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t- butyl, n-pentyl, i-pentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-nonyl, decyl, dodecyl, hexadecyl, benzyl, phenyl, naphthyl, biphenyl, fluorenyl, spirobifluorenyl, phenanthryl, anthryl, fluoranthenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, perylenyl, pyridyl, quinolyl, isoquinolyl or triazinyl, and the phenyl,
  • organic electroluminescent compound according to the present invention may be exemplified by the following compounds, but they do not limit the present invention.
  • the organic electroluminescent compound according to the present invention may be prepared by Scheme 1 :
  • the present invention also provides an organic electroluminescent device comprising: a first electrode; a second electrode; and one or more 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 used in a hole injection layer or a hole transport layer.
  • the organic layer may comprise one or more layer(s) comprising the organic electroluminescent compound represented by Chemical Formula 1 and one or more layer(s) comprising a fluorescent host and a fluorescent dopant or a phosphorescent host and a phosphorescent dopant.
  • the fluorescent host, the fluorescent dopant, the phosphorescent host and the phosphorescent dopant used in the organic electroluminescent device of the present invention are not particularly limited.
  • the organic layer may further comprise one or more metal(s) or complex(es) selected from a group consisting of organic metals of Group 1, Group 2, 4th period and 5th period transition metals, lanthanide metals and d- transition elements, and the organic layer may comprise an electroluminescent layer and a charge generating layer at the same time.
  • the organic layer may comprise one or more organic electroluminescent layer(s) emitting blue, red and green light at the same time, in addition to the aforesaid organic electroluminescent compound, to provide a white light-emitting electroluminescent device.
  • the compounds emitting blue, red or green light are exemplified in Korean Patent Application Nos. 10-2008-0123276, 10-2008-0107606 and 10-2008-0118428, but are not limited thereto.
  • 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 may be placed on the inner surface of one or both electrode(s) among the pair of electrodes.
  • injection and transport of electrons from the mixed region to the electroluminescent medium become easier because the electron transport compound is reduced to an anion.
  • injection and transport of holes from the mixed region to the electroluminescent medium become easier because the hole transport compound is oxidized to a cation.
  • Preferred examples of the oxidative dopant include various Lewis acids and acceptor compounds.
  • Preferred examples of the reductive dopant include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof.
  • the organic electroluminescent compound according to the present invention may improve luminous efficiency while lowering driving voltage of the device.
  • the organic compounds including carbazole derivatives have large triplet gap. Since they can more effectively block excitons in a phosphorescent device than existing materials, they may improve luminous efficiency and operation life of the device.
  • OLED (Samsung Corning) was subjected to ultrasonic washing sequentially using trichloroethylene, acetone, ethanol and distilled water, and stored in isopropanol for later use.
  • the ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus.
  • a vacuum deposition apparatus After adding 4,4',4"-tris(N,N-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) in a cell of the vacuum deposition apparatus, the pressure inside the chamber was reduced to 1O 6 torr. Then, 2-TNATA was evaporated by applying electrical current to the cell to form a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • An electroluminescent layer was formed on the hole transport layer as follows. 4,4'-N,N'-dicarbazole-biphenyl (CBP) was added in a cell of a vacuum deposition apparatus as a host material, and Compound D was added in another cell. The two cells were heated such that an electroluminescent layer having a thickness of 30 nm was formed on the hole transport layer at 2 to 5 wt% based on Compound D.
  • CBP 4,4'-N,N'-dicarbazole-biphenyl
  • Each OLED electroluminescent used in the OLED device had been purified by vacuum sublimation at 10 6 torr.
  • a hole injection layer was formed using 2-TNATA in the same manner as Example 1. Then, after adding N,N'-bis( ⁇ -naphthyl)-N, ⁇ /'-diphenyl-4,4'-diamine (NPB) in another cell of the vacuum deposition apparatus, NPBwas evaporated by applying electrical current to the cell to form a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • NPB N,N'-bis( ⁇ -naphthyl)-N, ⁇ /'-diphenyl-4,4'-diamine
  • Example 2 Luminous efficiency of the OLED devices manufactured in Example 1 and Comparative Example 1 was measured at 1,000 cd/m 2 . The result is given in Table 2.
  • An ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus in the same manner as Example 1. After adding Compound 12 in a cell of the vacuum deposition apparatus, the pressure inside the chamber was reduced to 10 6 torr. Then, Compound 12 was evaporated by applying electrical current to the cell to form a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • NPB N,N'-bis( ⁇ -naphthyl)-N,N'-diphenyl-4,4'-diamine

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne de nouveaux composés organiques électroluminescents, et un dispositif organique électroluminescent les comprenant. Quand il est inclus dans une couche d'injection de trous ou dans une couche de transport de trous d'un dispositif organique électroluminescent, le composé organique électroluminescent de l'invention permet d'améliorer le rendement lumineux tout en abaissant la tension d'attaque du dispositif.
PCT/KR2010/001691 2009-03-23 2010-03-18 Nouveaux composés organiques électroluminescents, et dispositif organique électroluminescent les utilisant WO2010110553A2 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2012501926A JP5778127B2 (ja) 2009-03-23 2010-03-18 新規有機電界発光化合物およびこれを使用する有機電界発光素子
CN2010800212132A CN102449106A (zh) 2009-03-23 2010-03-18 新颖的有机电致发光化合物和使用该化合物的有机电致发光器件

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020090024431A KR20100106014A (ko) 2009-03-23 2009-03-23 신규한 유기 발광 화합물 및 이를 포함하고 있는 유기 전계발광 소자
KR10-2009-0024431 2009-03-23

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WO2010110553A2 true WO2010110553A2 (fr) 2010-09-30
WO2010110553A3 WO2010110553A3 (fr) 2010-12-09

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KR (1) KR20100106014A (fr)
CN (1) CN102449106A (fr)
TW (1) TW201105770A (fr)
WO (1) WO2010110553A2 (fr)

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WO2011040607A1 (fr) * 2009-10-02 2011-04-07 出光興産株式会社 Dérivé aminé aromatique, et élément électroluminescent organique
CN102030702A (zh) * 2010-12-01 2011-04-27 天津市佰斯康科技有限公司 一种空穴传输材料及其合成方法
EP2371828A1 (fr) * 2010-04-01 2011-10-05 Samsung Mobile Display Co., Ltd. Composé cyclique condensé et dispositif électroluminescent organique l'incluant
WO2012001969A1 (fr) * 2010-06-30 2012-01-05 出光興産株式会社 Dérivé d'amine aromatique et élément électroluminescent organique à base de ce dérivé
WO2012015265A1 (fr) * 2010-07-29 2012-02-02 Rohm And Haas Electronic Materials Korea Ltd Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique à base de ces composés
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CN103249800A (zh) * 2010-10-13 2013-08-14 罗门哈斯电子材料韩国有限公司 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
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JP2014531420A (ja) * 2011-09-01 2014-11-27 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 ベンゾカルバゾール化合物およびそれらを含むエレクトロルミネッセンスデバイス
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KR20160080059A (ko) 2014-12-26 2016-07-07 삼성디스플레이 주식회사 유기 전계 발광 소자용 재료 및 이를 포함하는 유기 전계 발광 소자
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JP5778127B2 (ja) 2015-09-16
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TW201105770A (en) 2011-02-16
CN102449106A (zh) 2012-05-09
WO2010110553A3 (fr) 2010-12-09

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