WO2014017844A1 - Composé émettant de la lumière organique comprenant des dérivés d'acridine, et dispositif émettant de la lumière organique le comprenant - Google Patents

Composé émettant de la lumière organique comprenant des dérivés d'acridine, et dispositif émettant de la lumière organique le comprenant Download PDF

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WO2014017844A1
WO2014017844A1 PCT/KR2013/006669 KR2013006669W WO2014017844A1 WO 2014017844 A1 WO2014017844 A1 WO 2014017844A1 KR 2013006669 W KR2013006669 W KR 2013006669W WO 2014017844 A1 WO2014017844 A1 WO 2014017844A1
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compound
light emitting
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organic light
formula
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함호완
안현철
김동준
한정우
김근태
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주식회사 동진쎄미켐
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Priority claimed from KR1020130087572A external-priority patent/KR102169273B1/ko
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Priority to CN201380038477.2A priority Critical patent/CN104471022B/zh
Publication of WO2014017844A1 publication Critical patent/WO2014017844A1/fr

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Definitions

  • the present invention relates to an organic light emitting compound comprising an acridine derivative 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 organic light emitting device has a structure including a cathode (electron injection electrode) and an anode (hole injection electrode), and an organic material layer between the two electrodes.
  • the organic material layer may include a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer (EIL) in addition to the light emitting layer (EML).
  • HIL hole injection layer
  • HTL hole transport layer
  • ETL electron transport layer
  • EIL electron injection layer
  • an electron injection layer and may further include an electron blocking layer (EBL) or a hole blocking layer (HBL) due to the light emission characteristics of the light emitting layer.
  • EBL electron blocking layer
  • HBL hole blocking layer
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to realize better natural colors according to light emission colors.
  • the light emitting layer (dopant) may be doped into the light emitting layer (host). The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the 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.
  • an object of the present invention is to provide a novel organic light emitting compound with improved color purity, luminous efficiency, luminance, power efficiency, heat resistance and the like.
  • Another object of the present invention is to provide an organic light emitting device including the compound, which exhibits low driving voltage, high luminous efficiency and luminous luminance, and is capable of long life.
  • the present invention provides an organic light emitting compound comprising an acridine derivative represented by the following formula (1):
  • X is substituted or unsubstituted C, O, P, S, Se or Si, and when X is O, the nitrogen atom of the acridine cannot be bonded at position 3 of the heteroaryl moiety;
  • R 1 to R 17 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 6-36 aryl group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; Or a C 2-36 heteroaryl
  • X and R 1 to R 17 are the same as defined in Chemical Formula 1.
  • the present invention also provides an organic light emitting device comprising the compound represented by Chemical Formula 1 in an organic material layer as a light emitting material.
  • the organic light emitting compound of the present invention is excellent in brightness, power efficiency, heat resistance, charge transport performance and charge injection performance by controlling the charge balance in the organic layer through the appropriate combination of the acridine derivative and the cyclic compound, the color purity and luminous efficiency Since it can be increased, it can be applied to one or more of the functional layer material of the organic light emitting device and the host or dopant of the light emitting layer. Therefore, the organic light emitting device including the compound of the present invention exhibits low driving voltage, high luminous luminance and luminous efficiency, and thus can maximize performance and improve lifespan in a full color organic panel.
  • FIG. 1 schematically shows a cross section of an OLED according to an embodiment of the invention
  • FIG. 2 shows a band diagram of an organic light emitting diode having a light emission principle due to an organic light emitting phenomenon.
  • the compound of the present invention represented by Formula 1 is characterized in that an acridine moiety and an aryl or heteroaryl moiety are directly connected to the nitrogen atom of the acridine:
  • X is substituted or unsubstituted C, O, P, S, Se or Si, and when X is O, the nitrogen atom of the acridine cannot be bonded at position 3 of the heteroaryl moiety;
  • R 1 to R 17 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 6-36 aryl group which is unsubstituted or substituted with deuterium, halogen, amino, nitrile or nitro group; Or a C 2-36 heteroaryl
  • R 1 to R 10 are each substituted with deuterium, they may be deuterated at least 20%, preferably at least 40%, and more preferably at least 50% of R 1 to R 10 .
  • aryl or heteroaryl moiety directly connected to the nitrogen atom of the acridine-based moiety in the compound is substituted with deuterium, it is preferably at least 50% deuterated.
  • substituents of X and R 1 to R 17 are each independently deuterium, halogen, nitrile group, nitro group, C 1-30 alkyl group, C 1-30 alkoxy group, C 3-30 cycloalkyl group, C 3-30 heterocycloalkyl group, C 6-30 aryl group, C 5-30 heteroaryl group, C 1-30 alkyloxy group, C 6-30 aryloxy group and C 6-30 arylamine It is preferably substituted with one or more substituents selected from the group consisting of groups, but is not limited thereto, and adjacent groups may be bonded to each other to form a saturated or unsaturated carbon ring.
  • the compound of formula 1 according to the present invention has an acridine-based moiety and an aryl- or heteroaryl-based moiety directly linked to the nitrogen atom of acridine so that the compound of the acridine derivative and the cyclic compound in the organic layer Adjust the charge balance.
  • the luminance, power efficiency, heat resistance, charge transport performance, and charge injection performance can be improved to increase color purity and luminous efficiency. Therefore, the present invention can be applied to one or more of the functional layer material of the organic light emitting device and the host or dopant of the light emitting layer. have.
  • the compound of the present invention when applied to an organic light emitting device, it is possible to improve characteristics such as driving voltage and luminous efficiency of the light emitting device.
  • the present invention provides a method for preparing Formula 1 comprising the step of reacting the following Formula 1-1 and Formula 1-2:
  • X and R 1 to R 17 are the same as defined in Chemical Formula 1.
  • the compound of Formula 1 according to the present invention may be prepared according to the method according to Scheme 1 below.
  • X is as defined in Formula 1, and each R corresponds to R 1 and R 2 of Formula 1-1, respectively.
  • the present invention provides an organic light emitting device comprising a compound represented by the formula (1) in the organic material layer as a light emitting material.
  • the compound of the present invention may be used alone or in combination with a known organic light emitting compound.
  • 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 electrode by a method such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), or the like. It is preferable to form by the vacuum evaporation method in that it is hard to generate
  • a method such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB), or the like. 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 hole injection layer material is not particularly limited, and TCTA (4,4 ′, 4 ′′ -tri (N-carbazolyl) tree, which is a phthalocyanine compound or starburst type amine derivative such as copper phthalocyanine disclosed in US Pat. No. 4,356,429.
  • 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 is not particularly limited, and may be arbitrarily selected and used from conventionally known materials used in the hole transport layer.
  • the hole transport layer material is carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-ratio Ordinary amines having aromatic condensed rings such as phenyl] -4,4'-diamine (TPD), N.N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine ( ⁇ -NPD) Derivatives and the like can be used.
  • carbazole derivatives such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-ratio Ordinary amines having aromatic condensed rings such as phenyl] -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 use the compound represented by Formula 1 of the present invention as a host or dopant.
  • a light emitting layer may be formed by using a phosphorescent or fluorescent dopant together.
  • the fluorescent dopant may be IDE102 or IDE105, or BD142 (N 6 , N 12 -bis (3,4-dimethylphenyl) -N 6 , N 12 -dimethyrylcrisne- which can be purchased from Idemitsu Co., Ltd.).
  • 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 content of the dopant is less than 0.01 parts by weight, there is a problem in that the color development is not performed properly because the amount of the dopant is not sufficient, and if it exceeds 15 parts by weight, the efficiency is drastically reduced due to the concentration quenching phenomenon.
  • 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 material as a function to transport a steady stream of electrons injected from the electron injecting electrode that kind is not particularly limited, for example, 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 compound of the present invention is excellent in brightness, power efficiency, heat resistance, charge transport performance and charge injection performance to increase the color purity and luminous efficiency, it is used as a light emitting material of the organic light emitting device is low driving voltage to the organic light emitting device And high luminous luminance and luminous efficiency, which can provide maximum performance and longer life in full color organic panels.
  • Compound 5 was obtained by the same method as the synthesis method of Compound 1, except that bromodibenzo [b, d] furan (247.09) and 4-bromodibenzo [b, d] furan were reacted with 1-bromodibenzo [b, d] furan. Got it.
  • Compound 10 was obtained by the same method as the synthesis method of compound 9, except that diphenylamine was reacted with 9H-carbazole.
  • Compound 13 was obtained by the same method as the synthesis method of compound 12, except that diphenylamine was reacted with 9H-carbazole.
  • An organic light emitting diode was manufactured in the same structure as in FIG. 1. Specifically, the glass substrate coated with a 1500 ⁇ m thick indium tin oxide (ITO) was washed with distilled water ultrasonic waves. After the distilled water is washed, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried, transferred to a plasma cleaner, and the substrate is cleaned for 5 minutes using an oxygen plasma. Using an evaporator, 2-TNATA 600 ⁇ was formed as a hole injection layer and NPB 200 ⁇ was formed as a hole transport layer.
  • ITO indium tin oxide
  • the host material of Examples 1 to 20 synthesized in the above Example was doped with Ir (ppy) 3 7% to form 300 ⁇ .
  • TPBi 300 ⁇ was formed into an electron transport layer, followed by LiF 10 ⁇ and aluminum (Al) 1000 ⁇ , which were encapsulated in a glove box to produce an organic light emitting device.
  • a glass substrate coated with an indium tin oxide (ITO) 1500 ⁇ thick thin film was washed by distilled water ultrasonically. After the distilled water is washed, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried, transferred to a plasma cleaner, and the substrate is cleaned for 5 minutes using an oxygen plasma.
  • 2-TNATA 600 ⁇ was used as the hole injection layer, and 200 ⁇ of the compound synthesized in Examples 1 to 20 was formed into a hole transport layer using an evaporator.
  • mCP was doped with Ir (ppy) 3 7% to form 300 ⁇ .
  • TPBi 300 ⁇ was formed into an electron transport layer, followed by LiF 10 ⁇ and aluminum (Al) 1000 ⁇ .
  • the organic light emitting device was manufactured by encapsulating the device in a glove box.
  • An organic light emitting diode was manufactured according to the same method as the hole transport layer and the light emitting layer host, except for using NPB and mCP.
  • Example 21 ITO / 2-TNATA / NPB / Compound 1: Ir (ppy) 3 (7%) / TPBi / LiF / Al 38.5 17.7 18
  • Example 22 ITO / 2-TNATA / NPB / Compound 2: Ir (ppy) 3 (7%) / TPBi / LiF / Al 39.2 17.9 18.3
  • Example 23 ITO / 2-TNATA / NPB / Compound 3: Ir (ppy) 3 (7%) / TPBi / LiF / Al 40 19 19.2
  • Example 24 ITO / 2-TNATA / NPB / Compound 4: Ir (ppy) 3 (7%) / TPBi / LiF / Al 41 19.3 20
  • Example 25 ITO / 2-TNATA / NPB / Compound 5: Ir (ppy) 3 (7%) / TPBi / LiF / Al 38.2 17.8 16.9
  • Example 26 ITO / 2-TNATA / NPB / Compound 1: Ir (
  • the organic light emitting compound of the present invention is excellent in brightness, power efficiency, heat resistance, charge transport performance and charge injection performance by controlling the charge balance in the organic layer through the appropriate combination of the acridine derivative and the cyclic compound, the color purity and luminous efficiency Since it can be increased, it can be applied to one or more of the functional layer material of the organic light emitting device and the host or dopant of the light emitting layer. Therefore, the organic light emitting device including the compound of the present invention exhibits low driving voltage, high luminous luminance and luminous efficiency, and thus can maximize performance and improve lifespan in a full color organic panel.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
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  • Electroluminescent Light Sources (AREA)

Abstract

Le composé émettant de la lumière organique comprenant des dérivés d'acridine selon la présente invention ajuste l'équilibre de charge dans une couche de matière organique par des moyens comprenant un équilibre approprié entre les dérivés d'acridine et un composé cyclique, permettant ainsi d'obtenir une excellente luminance, un excellent rendement énergétique, une excellente résistance thermique, une excellente performance de transport de charge et une excellente performance d'injection de charge pour ainsi augmenter la pureté de couleur et le rendement lumineux. En conséquence, le composé émettant de la lumière organique de la présente invention peut être utilisé comme matière émettant de la lumière pour un dispositif émettant de la lumière organique de façon à présenter une faible tension de commande et une luminance élevée et un rendement lumineux élevé pour un dispositif émettant de la lumière organique, permettant ainsi la performance rendue maximale et la durée de vie améliorée d'un panneau organique de couleur totale.
PCT/KR2013/006669 2012-07-26 2013-07-25 Composé émettant de la lumière organique comprenant des dérivés d'acridine, et dispositif émettant de la lumière organique le comprenant WO2014017844A1 (fr)

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JP2016130231A (ja) * 2015-01-08 2016-07-21 国立大学法人九州大学 化合物、混合物、発光層、有機発光素子およびアシストドーパント
CN106220645A (zh) * 2016-04-25 2016-12-14 中节能万润股份有限公司 一种基于单取代基-9-芴酮的化合物及其应用
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TWI588132B (zh) * 2014-11-12 2017-06-21 Ｌｇ顯示器股份有限公司 延遲螢光化合物、及有機發光二極體以及使用該有機發光二極體的顯示裝置
CN107068878A (zh) * 2016-04-25 2017-08-18 中节能万润股份有限公司 一种含单取代基-9-芴酮化合物的有机电致发光器件及其应用
US9954186B2 (en) 2014-11-12 2018-04-24 Lg Display Co., Ltd. Delayed fluorescence compound, and organic light emitting diode and display device using the same
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WO2018159663A1 (fr) * 2017-02-28 2018-09-07 国立大学法人九州大学 Matériaux luminescents, élément luminescent organique, et composés
CN108976212A (zh) * 2017-06-02 2018-12-11 北京鼎材科技有限公司 芴衍生物及其在有机发光材料中的应用
JP2021506822A (ja) * 2017-12-15 2021-02-22 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセントデバイスに使用するための置換芳香族アミン
US11228001B2 (en) 2017-01-20 2022-01-18 Lg Chem, Ltd. Hetero-cyclic compound and organic light emitting device comprising the same
US11440925B2 (en) 2016-11-08 2022-09-13 Merck Patent Gmbh Compounds for electronic devices
DE102021213722A1 (de) 2021-12-02 2023-06-07 Continental Reifen Deutschland Gmbh Verbindung, Kautschukmischung enthaltend die Verbindung, Fahrzeugreifen, der die Kautschukmischung in wenigstens einem Bauteil aufweist, Verfahren zur Herstellung der Verbindung sowie Verwendung der Verbindung als Alterungsschutzmittel und/oder Antioxidationsmittel und/oder Farbstoff
US11925113B2 (en) 2018-04-24 2024-03-05 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same

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US20170018720A1 (en) * 2014-03-11 2017-01-19 Hodogaya Chemical Co., Ltd. Spiro compound having azafluorene ring structure, light-emitting material, and organic electroluminescent device
US10916711B2 (en) * 2014-03-11 2021-02-09 Hodogaya Chemical Co., Ltd. Spiro compound having azafluorene ring structure, light-emitting material, and organic electroluminescent device
US10135005B2 (en) 2014-11-12 2018-11-20 Lg Display Co., Ltd. Delayed fluorescence compound, and organic light emitting diode and display device using the same
US10193085B2 (en) 2014-11-12 2019-01-29 Lg Display Co., Ltd. Delayed fluorescence compound, and organic light emitting diode and display device using the same
TWI588132B (zh) * 2014-11-12 2017-06-21 Ｌｇ顯示器股份有限公司 延遲螢光化合物、及有機發光二極體以及使用該有機發光二極體的顯示裝置
US10651399B2 (en) 2014-11-12 2020-05-12 Lg Display Co., Ltd. Delayed fluorescence compound, and organic light emitting diode and display device using the same
US9954186B2 (en) 2014-11-12 2018-04-24 Lg Display Co., Ltd. Delayed fluorescence compound, and organic light emitting diode and display device using the same
US9960372B2 (en) 2014-11-27 2018-05-01 Samsung Display Co., Ltd. Monoamine derivative and organic electroluminescent device including the same
JP2016130231A (ja) * 2015-01-08 2016-07-21 国立大学法人九州大学 化合物、混合物、発光層、有機発光素子およびアシストドーパント
WO2016111196A1 (fr) * 2015-01-08 2016-07-14 国立大学法人九州大学 Composé, mélange, couche photo-émettrice, élément électroluminescent organique, et dopant auxiliaire
CN107068878A (zh) * 2016-04-25 2017-08-18 中节能万润股份有限公司 一种含单取代基-9-芴酮化合物的有机电致发光器件及其应用
CN106220645A (zh) * 2016-04-25 2016-12-14 中节能万润股份有限公司 一种基于单取代基-9-芴酮的化合物及其应用
US11440925B2 (en) 2016-11-08 2022-09-13 Merck Patent Gmbh Compounds for electronic devices
US20180166636A1 (en) * 2016-12-13 2018-06-14 Lg Display Co., Ltd. Organic compound, and organic light-emitting diode and organic light-emitting diode display device including the same
US10700290B2 (en) * 2016-12-13 2020-06-30 Lg Display Co., Ltd. Organic compound, and organic light-emitting diode and organic light-emitting diode display device including the same
US11228001B2 (en) 2017-01-20 2022-01-18 Lg Chem, Ltd. Hetero-cyclic compound and organic light emitting device comprising the same
WO2018159663A1 (fr) * 2017-02-28 2018-09-07 国立大学法人九州大学 Matériaux luminescents, élément luminescent organique, et composés
CN108976212A (zh) * 2017-06-02 2018-12-11 北京鼎材科技有限公司 芴衍生物及其在有机发光材料中的应用
JP2021506822A (ja) * 2017-12-15 2021-02-22 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセントデバイスに使用するための置換芳香族アミン
US11925113B2 (en) 2018-04-24 2024-03-05 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
DE102021213722A1 (de) 2021-12-02 2023-06-07 Continental Reifen Deutschland Gmbh Verbindung, Kautschukmischung enthaltend die Verbindung, Fahrzeugreifen, der die Kautschukmischung in wenigstens einem Bauteil aufweist, Verfahren zur Herstellung der Verbindung sowie Verwendung der Verbindung als Alterungsschutzmittel und/oder Antioxidationsmittel und/oder Farbstoff
WO2023098953A1 (fr) 2021-12-02 2023-06-08 Continental Reifen Deutschland Gmbh Composé, mélange de caoutchouc contenant le composé, pneu de véhicule comprenant le mélange de caoutchouc dans au moins un composant, procédé de production du composé, et utilisation du composé comme agent anti-vieillissement et/ou anti-oxydant et/ou colorant

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