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WO2015084047A1 - Nouveau composé et élément électroluminescent organique comprenant ledit composé - Google Patents

Nouveau composé et élément électroluminescent organique comprenant ledit composé Download PDF

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WO2015084047A1
WO2015084047A1 PCT/KR2014/011757 KR2014011757W WO2015084047A1 WO 2015084047 A1 WO2015084047 A1 WO 2015084047A1 KR 2014011757 W KR2014011757 W KR 2014011757W WO 2015084047 A1 WO2015084047 A1 WO 2015084047A1
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group
compound
substituted
deuterium
halogen
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PCT/KR2014/011757
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English (en)
Korean (ko)
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함호완
김봉기
안현철
김성훈
김동준
한정우
김근태
임동환
조지은
Original Assignee
주식회사 동진쎄미켐
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Priority claimed from KR1020140169816A external-priority patent/KR102390954B1/ko
Application filed by 주식회사 동진쎄미켐 filed Critical 주식회사 동진쎄미켐
Priority to CN201480073934.6A priority Critical patent/CN105980371B/zh
Publication of WO2015084047A1 publication Critical patent/WO2015084047A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
    • 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
    • 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
    • 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
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic 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
    • 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
    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • an organic light emitting device capable of low voltage driving with a self-luminous type has a superior viewing angle, contrast ratio, and the like, and is lighter and thinner than a liquid crystal display (LCD), which is the mainstream of flat panel display devices.
  • LCD liquid crystal display
  • the material used as the organic material layer in the organic light emitting device can be largely classified into light emitting materials, hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on the function.
  • the present invention has a HOMO energy level easy hole injection, has a high LUMO energy level that can block electrons, excellent hole transport characteristics, hole injection layer of the organic light emitting device or It is an object of the present invention to provide a novel compound that can have excellent low voltage, high efficiency, high Tg stability and long life when applied to a hole transport layer.
  • Each X is independently O, S, Se or Te,
  • Ar 1 , Ar 2 , Ar 3 and Ar 4 are each independently deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 an aryl group of an alkynyl group, an alkoxy group of C 1-30, are C 6-30 aryloxy groups, be substituted by a heteroaryl group of the C 6-30 aryl group, or a C 2-30 substituted or the C 6-50; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group, and Ar 2 and Ar 3 may be connected to each other,
  • R 1 and R 2 are each independently hydrogen; heavy hydrogen; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-50 aryl group which is optionally substituted with deuterium, halogen, amino group, nitrile group, nitro group; Or a C 2-50 heteroaryl group unsub
  • n 1 or 2
  • n is an integer from 0 to 2
  • the present invention provides an organic light emitting device comprising the compound represented by the formula (1).
  • the compound of the present invention has a HOMO energy level that is easy to inject holes, has a high LUMO energy level that can block electrons, excellent hole transport characteristics, excellent low voltage when applied to the hole injection layer or hole transport layer of the organic light emitting device It has high stability, long life due to high efficiency and high Tg.
  • FIG. 1 schematically illustrates a cross section of an OLED according to an embodiment of the invention.
  • the compound of the present invention is characterized by represented by the following formula (1).
  • Each X is independently O, S, Se or Te,
  • Ar 1 , Ar 2 , Ar 3 and Ar 4 are each independently deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 an aryl group of an alkynyl group, an alkoxy group of C 1-30, are C 6-30 aryloxy groups, be substituted by a heteroaryl group of the C 6-30 aryl group, or a C 2-30 substituted or the C 6-50; Or deuterium, halogen, amino group, nitrile group, nitro group, C 1-30 alkyl group, C 2-30 alkenyl group, C 2-30 alkynyl group, C 1-30 alkoxy group, C 6-30 aryl Or a C 2-50 heteroaryl group which is unsubstituted or substituted with an oxy group, a C 6-30 aryl group, or a C 2-30 heteroaryl group, and Ar 2 and Ar 3 may be connected to each other,
  • R 1 and R 2 are each independently hydrogen; heavy hydrogen; C 1-30 alkyl group unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2-30 alkenyl groups unsubstituted or substituted with deuterium, halogen, amino, nitrile, and nitro groups; C 2-30 alkynyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; A C 1-30 alkoxy group unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-30 aryloxy group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; C 6-50 aryl group which is optionally substituted with deuterium, halogen, amino group, nitrile group, nitro group; Or a C 2-50 heteroaryl group unsub
  • n 1 or 2
  • n is an integer from 0 to 2
  • the compound represented by Chemical Formula 1 may be one of those represented by the following Chemical Formula 2 or 3.
  • Compound of Formula 1 according to the present invention has a HOMO energy level easy hole injection, has a high LUMO energy level that can block electrons, excellent hole transport characteristics, in the hole injection layer or hole transport layer of the organic light emitting device When applied, it can have excellent low voltage, high efficiency, high Tg stability and long life.
  • X, Ar 1 , Ar 2 , Ar 3 , Ar 4 , R 1 , R 2 , m and n are the same as defined in Formula 1, wherein R is R 1 or R 2 .
  • the present invention also provides an organic light emitting device comprising the compound represented by Chemical Formula 1 in an organic material layer.
  • the compound of the present invention is preferably used alone or in combination with a known compound as a hole injection material or a hole transport material.
  • the organic light emitting device of the present invention includes one or more organic material layers including the compound represented by Chemical Formula 1, and the method of manufacturing the organic light emitting device is as follows.
  • the organic light emitting device includes an organic material layer such as a hole injection layer (HIL), a hole transport layer (HTL), an emission layer (EML), an electron transport layer (ETL), an electron injection layer (EIL) between an anode and a cathode. It may contain one or more.
  • HIL hole injection layer
  • HTL hole transport layer
  • EML emission layer
  • ETL electron transport layer
  • EIL electron injection layer
  • an anode is formed by depositing a material for an anode electrode having a high work function on the substrate.
  • the substrate may be a substrate used in a conventional organic light emitting device, it is particularly preferable to use a glass substrate or a transparent plastic substrate excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproof.
  • the anode electrode material transparent and excellent indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and the like may be used.
  • the anode electrode material may be deposited by a conventional anode forming method, and specifically, may be deposited by a deposition method or a sputtering method.
  • the hole injection layer material may be formed on the anode by vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), etc., but it is easy to obtain a uniform film quality and also pinholes. It is preferable to form by the vacuum evaporation method in that it is hard to generate
  • the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the desired hole injection layer, and generally, a deposition temperature of 50-500 ° C., It is preferable to select appropriately from a vacuum degree of 10 -8 to 10 -3 torr, a deposition rate of 0.01 to 100 kPa / sec, and a layer thickness of 10 kPa to 5 mu m.
  • the compound represented by Formula 1 of the present invention may be used alone or a known hole injection layer material may be used.
  • a phthalocyanine compound or starburst such as copper phthalocyanine disclosed in US Pat. No. 4,356,429.
  • TCTA 4,4 ', 4 "-tri (N-carbazolyl) triphenylamine
  • m-MTDATA (4,4', 4" -tris (3-methylphenylamino) triphenylamine)
  • m-MTDAPB 4,4 ', 4 "-tris (3-methylphenylamino) phenoxybenzene
  • HI-406 N 1 , N 1 '-(biphenyl-4,4'-diyl) bis (N 1-(naphthalen- 1 -yl) -N 4 , N 4 -diphenylbenzene-1,4-diamine) and the like can be used as the hole injection layer material.
  • the hole transport layer material may be formed on the hole injection layer by a method such as vacuum deposition, spin coating, cast, LB, etc., but it is easy to obtain a uniform film quality and is difficult to generate pin holes. It is preferable to form by a vapor deposition method.
  • the deposition conditions vary depending on the compound used, but in general, the hole transport layer is preferably selected in the same condition range as the formation of the hole injection layer.
  • the hole transport layer material may be a compound represented by the formula (1) of the present invention may be used alone or a mixture of known hole transport layer materials.
  • the known hole transport layer material includes carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1, Having an aromatic condensed ring such as 1-biphenyl] -4,4'-diamine (TPD) and N.N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine ( ⁇ -NPD) Conventional amine derivatives and the like can be used.
  • carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1, Having an aromatic condensed ring such as 1-biphenyl] -4,
  • the light emitting layer material may be formed on the hole transport layer by a method such as vacuum deposition, spin coating, casting, LB, etc., but the vacuum deposition method is easy to obtain a uniform film quality and hard to generate pin holes. It is preferable to form by.
  • the deposition conditions vary depending on the compound used, but in general, it is preferable to select within the same condition range as the formation of the hole injection layer.
  • the light emitting layer material may be used as a known host or dopant.
  • a fluorescent dopant may be IDE102 or IDE105 available from Idemitsu, or BD142 (N 6 , N 12 -bis (3,4-dimethylphenyl) -N 6 , N 12 -dimethycrylicene- 6,12-diamine) can be used as green phosphorescent dopant Ir (ppy) 3 (tris (2-phenylpyridine) iridium), blue phosphorescent dopant F2Irpic (iridium (III) bis [4,6- Difluorophenyl) -pyridinato-N, C2 '] picolinate), a red phosphorescent dopant RD61 from UDC, and the like can be co-vacuum deposited (doped).
  • the doping concentration of the dopant is not particularly limited, but the dopant is preferably doped at 0.01 to 15 parts by weight based on 100 parts by weight of the host.
  • the hole suppression material HBL
  • HBL hole suppression material
  • the hole-suppressing material that can be used at this time is not particularly limited, but any one of the well-known ones used as the hole-inhibiting material can be selected and used.
  • an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or the hole-inhibiting material described in Japanese Patent Laid-Open No. 11-329734 (A1) can be cited.
  • Oxy-2-methylquinolinolato) -aluminum biphenoxide), a phenanthrolines-based compound e.g., BCP (vasocuproin) from UDC
  • BCP vasocuproin
  • An electron transport layer is formed on the light emitting layer formed as above, wherein the electron transport layer is formed by a vacuum deposition method, a spin coating method, a casting method, or the like, and is preferably formed by a vacuum deposition method.
  • the electron transport layer material functions to stably transport electrons injected from the electron injection electrode, and the type thereof is not particularly limited, and examples thereof include quinoline derivatives, especially tris (8-quinolinolato) aluminum (Alq 3). ), Or ET4 (6,6 '-(3,4-dimethyl-1,1-dimethyl-1H-silol-2,5-diyl) di-2,2'-bipyridine).
  • an electron injection layer (EIL) which is a material having a function of facilitating injection of electrons from the cathode, may be stacked on the electron transport layer, and the electron injection layer material may be LiF, NaCl, CsF, Li 2 O, BaO, or the like. The substance of can be used.
  • the deposition conditions of the electron transport layer are different depending on the compound used, it is generally preferable to select within the same condition range as the formation of the hole injection layer.
  • an electron injection layer material may be formed on the electron transport layer, wherein the electron transport layer is formed of a conventional electron injection layer material by a vacuum deposition method, a spin coating method, a casting method, and the like. It is preferable to form by.
  • a cathode forming metal is formed on the electron injection layer by a method such as vacuum deposition or sputtering and used as a cathode.
  • the cathode forming metal may be a metal having low work function, an alloy, an electrically conductive compound, and a mixture thereof. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and the like. There is this.
  • a transmissive cathode using ITO or IZO may be used to obtain the front light emitting device.
  • the organic light emitting device of the present invention is not only an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an organic light emitting device of the cathode structure, but also the structure of an organic light emitting device of various structures, 1 It is also possible to form a layer or two intermediate layers.
  • each organic material layer formed according to the present invention can be adjusted according to the required degree, preferably 10 to 1,000 nm, more preferably 20 to 150 nm.
  • the present invention has an advantage that the organic material layer including the compound represented by Formula 1 has a uniform surface and excellent shape stability because the thickness of the organic material layer can be adjusted in molecular units.
  • the organic light emitting device of the present invention has improved hole injection and hole transport characteristics, and at the same time has electron blocking characteristics, and excellent device characteristics such as excellent low voltage, high efficiency, stability due to high Tg, and long life.
  • Example 1 N-([1,1'-biphenyl] -4-yl)-[1,1 ': 4', 1 'instead of di ([1,1'-biphenyl] -4-yl) amine
  • Compound 3 was synthesized in the same manner as Compound 1 using '-terphenyl] -4-amine.
  • Compound 16 was synthesized in the same manner as compound 3 using intermediate C instead of intermediate A.
  • An organic light emitting device was manufactured according to the structure of FIG. 1.
  • the organic light emitting element is formed from the bottom of the anode (hole injection electrode 11) / hole injection layer 12 / hole transport layer 13 / light emitting layer 14 / electron transfer layer 15 / cathode (electron injection electrode 16) It was laminated in order.
  • the hole injection layer 12, the hole transport layer 13, the light emitting layer 14, and the electron transport layer 15 of Examples and Comparative Examples used the following materials.
  • a glass substrate coated with an indium tin oxide (ITO) 1500 ⁇ thick thin film was washed by distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried and transferred to a plasma cleaner, and then cleaned the substrate using oxygen plasma for 5 minutes and then a thermal vacuum evaporator (thermal Compound 1 250 Hz was formed into a hole injection layer HT01 600 Hz and a hole transport layer using the evaporator. Next, the light emitting layer was doped with BH01: BD01 5% to form 250 ⁇ . Next, ET01: Liq (1: 1) 300 ⁇ was formed into an electron transport layer, followed by LiF 10 ⁇ and aluminum (Al) 1000 ⁇ .
  • ITO indium tin oxide
  • a device was manufactured in the same manner as in Example 1, except that Compound 1 was used as NPB instead of Compound 1 as the hole transport layer.
  • a device was manufactured in the same manner as in Example 1, except that Compound 1 was used as Comparative Compound 1 instead of Compound 1 as a hole transport layer.
  • the embodiments of the present invention can be confirmed that the physical properties are excellent in all aspects compared to Comparative Example 1 and Comparative Example 2. It can be seen that the present compound has low voltage driving, high efficiency and long life due to easy hole injection and excellent hole transport.
  • the compound of the present invention has a HOMO energy level that is easy to inject holes, has a high LUMO energy level that can block electrons, excellent hole transport characteristics, excellent low voltage when applied to the hole injection layer or hole transport layer of the organic light emitting device It has high stability, long life due to high efficiency and high Tg.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Un composé selon la présente invention présente un niveau d'énergie HOMO facilitant l'injection de trous, un niveau élevé d'énergie LUMO capable de bloquer les électrons, de remarquables caractéristiques en matière de transport de trous, et, lorsqu'il est utilisé dans une couche d'injection de trous ou dans une couche de transport de trous d'un élément électroluminescent organique, ledit composé peut stabiliser ladite couche et lui assurer une plus longue durée de vie du fait d'une tension électrique particulièrement basse, d'un grand rendement et d'une température de transition vitreuse élevée.
PCT/KR2014/011757 2013-12-04 2014-12-03 Nouveau composé et élément électroluminescent organique comprenant ledit composé WO2015084047A1 (fr)

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KR10-2013-0149608 2013-12-04
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KR1020140169816A KR102390954B1 (ko) 2013-12-04 2014-12-01 신규한 화합물 및 이를 포함하는 유기발광소자

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Cited By (3)

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Publication number Priority date Publication date Assignee Title
CN105176132A (zh) * 2015-10-23 2015-12-23 湘潭大学 一种含有三苯胺-噻吩芴衍生物的有机染料敏化剂及其制备方法
US10973817B2 (en) 2014-02-10 2021-04-13 Sentinel Oncology Limited Pharmaceutical compounds
WO2021132995A1 (fr) * 2019-12-27 2021-07-01 엘티소재주식회사 Élément électroluminescent organique et composition pour couche de matériau organique de celui-ci

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JP2008156261A (ja) * 2006-12-22 2008-07-10 Univ Nagoya 架橋スチルベン誘導体およびそれらを用いた有機電界発光素子
KR20100082676A (ko) * 2009-01-09 2010-07-19 주식회사 엘지화학 신규한 화합물, 그 유도체 및 이를 이용한 유기전자소자
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Cited By (8)

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KR102594398B1 (ko) * 2019-12-27 2023-10-27 엘티소재주식회사 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물
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