WO2011081451A2 - Composés triphénylés, et dispositif électroluminescent organique les utilisant - Google Patents

Composés triphénylés, et dispositif électroluminescent organique les utilisant Download PDF

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WO2011081451A2
WO2011081451A2 PCT/KR2010/009508 KR2010009508W WO2011081451A2 WO 2011081451 A2 WO2011081451 A2 WO 2011081451A2 KR 2010009508 W KR2010009508 W KR 2010009508W WO 2011081451 A2 WO2011081451 A2 WO 2011081451A2
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unsubstituted
substituted
aryl
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WO2011081451A3 (fr
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김신한
김태형
김경수
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주식회사 두산
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Definitions

  • the present invention includes a novel triphenylene compound having excellent electron transporting ability, hole injection and / or transporting ability, and / or luminous ability, and including the same in at least one organic layer, such as luminous efficiency, luminance, thermal stability, driving voltage, and lifetime. This is an improved organic electroluminescent device.
  • organic light emitting phenomenon refers to a phenomenon in which light appears when electric energy is applied to an organic material.
  • a voltage is applied between the two electrodes, and holes are injected into the organic layer and electrons are injected into the cathode.
  • excitons are formed, and when the excitons fall back to the ground, they shine.
  • organic electroluminescent (EL) devices led to blue electroluminescence using anthracene monocrystals in 1965, based on Bernanose's observation of organic thin film emission in the 1950s.
  • EL organic electroluminescent
  • an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer has been proposed, and has been developed in the form of introducing each characteristic organic material layer in the device to make a high efficiency and long life organic EL device. This led to the development of specialized materials used for this.
  • Such organic EL devices include an indium tin oxide (ITO) substrate, an anode, a hole injection layer that selectively receives holes from an anode, a hole transport layer that selectively transfers holes, a light emitting layer where holes and electrons recombine to emit light, and optionally an electron It consists of an electron transporting layer for transferring the electrons, optionally an electron injection layer for receiving electrons from the cathode and the cathode.
  • ITO indium tin oxide
  • the reason why the organic EL device is manufactured in multiple layers is that the movement speeds of the holes and the electrons are different. If the appropriate hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer are made, the holes and the electrons can be effectively transferred. The balance between the holes and the electrons in the device can be achieved to increase the luminous efficiency.
  • Electrons injected from the electron injection layer and holes transferred from the hole injection layer recombine in the emission layer to form excitons, and fall from the singlet excited state to the ground state and are called fluorescence, and fall from the triplet excited state to the ground state.
  • Luminescence is called phosphorescence. Theoretically, when the exciton is generated when the carrier is recombined in the emission layer, the ratio of singlet and triplet excitons is generated at a ratio of 1: 3, and when phosphorescence is used, the internal quantum efficiency may be 100%.
  • carbazole compounds such as CBP (4,4-dicarbazolybiphenyl) are used as the phosphorescent host material, and metal complex compounds containing heavy atoms such as Ir and Pt are widely used as the phosphorescent dopant material. It is used.
  • CBP which is currently used phosphorescent host material
  • Tg glass transition temperature
  • an object of the present invention is to provide a triphenylene-based compound having excellent electron transporting ability, hole injection and / or transporting ability, and / or light emitting ability (fluorescence or phosphorescence) and light emission efficiency, brightness, and thermal stability by including the same in at least one organic layer.
  • a triphenylene-based compound having excellent electron transporting ability, hole injection and / or transporting ability, and / or light emitting ability (fluorescence or phosphorescence) and light emission efficiency, brightness, and thermal stability by including the same in at least one organic layer.
  • the present invention provides a compound represented by the following formula (1):
  • X is a sulfur or oxygen atom
  • R 1 to R 20 are each independently hydrogen, deuterium, halogen, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted nuclear atom having 3 to 60 heterocycles, substituted or unsubstituted nuclear atom having 5 to 40 heteroaryl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C3-C40 cycloalkyl, substituted or unsubstituted heterocycloalkyl having 3 to 40 nuclear atoms, substituted or unsubstituted C5-C40 aryl, Substituted or unsubstituted C5-C60 aryloxy, (substituted or unsubstituted C5-C60 aryl) C1-C40 alkyl, substituted or unsubstituted C2-C40 alkenyl, substituted or unsubstituted C1-C40 alkylamine, ( Substituted or
  • L is substituted or unsubstituted C5-C60 aryl, substituted or unsubstituted heteroatom having 3 to 60 heteroatoms, substituted or unsubstituted heteroatom having 5 to 40 heteroaryl, (substituted or unsubstituted C5- C60 aryl) C1-C40 alkyl, substituted or unsubstituted C5-C40 arylamine, substituted or unsubstituted C5-C60 aryloxy, substituted or unsubstituted C5-C40 arylsilyl, or substituted or unsubstituted C7-C40 Ketoaryl, when L has a substituent, adjacent substituents may be bonded to each other to form a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, or a fused heteroaromatic ring having 5 to 40 nuclear atoms.
  • the present invention the anode; cathode; And at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers includes the compound described above.
  • the compound of Chemical Formula 1 according to the present invention is used as a material for organic EL devices, and when used as a blue, green fluorescent or phosphorescent host material through a wide energy band gap, to 4,4-dicarbazolybiphenyl (CBP) conventionally used.
  • CBP 4,4-dicarbazolybiphenyl
  • Low power, high efficiency, high brightness, and improved durability and lifespan can be achieved.
  • the organic EL device including the compound of the present invention can be greatly improved in terms of light emitting performance and lifetime, and thus can be effectively applied to a full color display panel and the like.
  • the present invention provides a compound represented by the formula (1), specifically, a triphenylene moiety that does not adequately exhibit its properties as a phosphorescent host due to inadequate triplet energy level, through a linker (L) containing an aryl group.
  • a linker (L) containing an aryl group By connecting the S-containing fused heterocyclic moieties with orbitals, the effect of stably forming triplet energy states through orbital mixing is induced, while the excited energy levels by functional groups
  • the desired energy bandgap of 3.0 eV ⁇ ⁇ 4.1 eV through the control of, it is possible to induce the triplet-triplet energy transition with a general phosphorescent dopant, and the phosphorescence of the device Triphenylene compounds having improved properties and improved electron and / or hole transport ability, luminous efficiency, driving voltage and lifetime characteristics ( triphenylene-based compounds).
  • X is a sulfur or oxygen atom.
  • R 1 to R 20 are each independently hydrogen or an optional substituent, and such substituents are not particularly limited as long as they can form a desirable energy bandgap, and non-limiting examples thereof are deuterium, halogen, substituted or unsubstituted C1.
  • -C40 alkyl (preferably C1-C8 alkyl), substituted or unsubstituted heterocyclic ring having 3 to 60 nuclear atoms (preferably heterocyclic ring having 3 to 24 nuclear atoms), substituted or unsubstituted nucleus Heteroaryl having 5 to 40 atoms (preferably heteroaryl having 5 to 24 nuclear atoms), substituted or unsubstituted C1-C40 alkoxy (preferably C1-C18 alkoxy), substituted or unsubstituted C3 -C40 cycloalkyl (preferably C3-C18 cycloalkyl), substituted or unsubstituted heterocycloalkyl having 3 to 40 nuclear atoms (preferably heterocycloalkyl having 3 to 18 nuclear atoms), substituted or Unsubstituted C5-C40 aryl (bar Directly C5-C24 aryl), substituted or unsubstituted C5-C60 aryloxy (preferably C5-C24 ary
  • the linker L is substituted or unsubstituted C5-C60 aryl, substituted or unsubstituted heteroatoms having 3 to 60 nuclear atoms, substituted or unsubstituted heteroaryl atoms having 5 to 40 heteroatoms, (substituted or unsubstituted C5-C60 aryl) C1-C40 alkyl, substituted or unsubstituted C5-C40 arylamine, substituted or unsubstituted C5-C60 aryloxy, substituted or unsubstituted C5-C40 arylsilyl, or substituted or unsubstituted C7 -C40 ketoaryl, where L has a substituent, adjacent substituents may be bonded to each other to form a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring having 5 to 40 nuclear atoms; have.
  • ketoaryl and haloalkyl are each independently deuterium, halogen, C1-C40 alkyl, heterocycle having 3 to 60 nuclear atoms, heteroaryl having 5 to 40 nuclear atoms, C1-C40 alkoxy, C3-C40 cyclo Alkyl, heterocycloalkyl of 3 to 40 nuclear atoms, C5-C40 aryl, C5-C60 aryloxy, (C5-C60 aryl) C1-C40 alkyl, C2-C40 alkenyl, C1-C40 alkylamine, (C5- C60 aryl) C1-
  • X, L, R 1 to R 20 are as defined above.
  • the linker L may be selected from the group consisting of
  • the linker L may also be selected from the group consisting of
  • R 21 and R 22 are as defined above,
  • At least one of the plurality of Z is a nitrogen atom and the rest are carbon atoms, and the hydrogen atom attached to Z is unsubstituted or deuterium, halogen, substituted or unsubstituted C1-C40 alkyl, substituted or unsubstituted nuclear atom, 3 to 3 Heteroaryl of 60, substituted or unsubstituted heteroaryl 5 to 40 heteroaryl, substituted or unsubstituted C1-C40 alkoxy, substituted or unsubstituted C3-C40 cycloalkyl, substituted or unsubstituted nuclear 3 To 40 heterocycloalkyl, substituted or unsubstituted C5-C40 aryl, substituted or unsubstituted C5-C60 aryloxy, (substituted or unsubstituted C5-C60 aryl) C1-C40 alkyl, substituted or unsubstituted C2 -C40 alkeny
  • the linker L is preferably a form in which the triphenylene and the S-containing condensed ring are linked by a meta bond.
  • unsubstituted alkyl is a straight or branched chain saturated hydrocarbon of 1 to 40 carbon atoms, examples being methyl, ethyl, propyl, isobutyl. sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • Unsubstituted cycloalkyl includes monocyclic or polycyclic non-aromatic hydrocarbon groups having 3 to 40 carbon atoms. Examples of such cycloalkyls include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, and the like.
  • Unsubstituted alkoxy means alkyl with 1 to 40 carbon atoms attached to oxygen and is interpreted to include a linear, branched or cyclic structure. Examples of alkoxy may include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Unsubstituted heterocycle means an aromatic and / or non-aromatic ring having 3 to 60 nuclear atoms, wherein one or more carbons in the ring, preferably 1 to 3 carbons, are N, O or S And substituted with a heteroatom such as
  • Non-limiting examples of heterocycles include 3-1H-benzimidazol-2-one, 2-tetrahydrofuranyl, 2-tetrahydrothiophenyl, 2-morpholinyl, 3-morpholinyl, 1-pyrroli Diyl, 1-piperazinyl, 2-piperazinyl, 4-thiazolidinyl, benzoxanyl, benzopyrrolidinyl, benzopiperidinyl, benzothianyl, etc. This includes.
  • the heterocycles used herein are to be understood to include those condensed with one or more aromatic or non-aromatic rings.
  • the heterocycle may be used in a superposition with heterocycloalkyl and heteroaryl.
  • Unsubstituted aryl means an aromatic moiety having 5 to 60 carbon atoms, singly or in combination of two or more rings, and is referred to herein as "aryloxy”, “arylalkyl”, “arylsilyl”, and the like. Two or more rings may be attached in a simple or fused form with one another. Examples of aryl include, but are not limited to, phenyl, hydroxyphenyl, alkoxyphenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Unsubstituted heteroaryl means a monoheterocyclic or polyheterocyclic aromatic moiety having 5 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O or S And substituted with a heteroatom such as It is understood that two or more rings may be attached in a simple or fused form to each other and further include a condensed form with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl It is understood to include a ring and to include 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
  • Unsubstituted heterocycloalkyl means a non-aromatic moiety of 3 to 40 nuclear atoms, in which one or more carbons in the ring, preferably 1 to 3 carbons, are replaced with a hetero atom such as N, O or S .
  • Non-limiting examples thereof include morpholine, piperazine and the like.
  • Unsubstituted alkenyl means a radical comprising at least one carbon-carbon double bond at the center or terminus of an alkyl having from 2 to 40 carbon atoms.
  • alkenyl include, but are not limited to, ethylene, propylene, butylene, hexylene, and the like.
  • Unsubstituted aryloxy includes phenyloxy, naphthyloxy, diphenyloxy and the like having 5 to 60 carbon atoms, and "unsubstituted arylalkyl” is also called aralkyl and benzyl, phenylethyl And the like.
  • Alkylsilyl is silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl is silyl substituted with aryl having 5 to 40 carbon atoms
  • ketoaryl means aryl having a carbonyl group attached thereto.
  • Haloalkyl refers to alkyl substituted with halogen atoms such as fluorine, chlorine, bromine and the like.
  • the invention also includes an anode; Cathode; And at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer comprises a compound represented by Formula 1 above. To provide.
  • the compound of Formula 1 may be included alone or in plurality.
  • the organic layer including the compound of Formula 1 of the present invention may be any one or more of a hole injection layer, a hole transport layer, an electron transport layer and a light emitting layer.
  • the light emitting layer may include a phosphorescent dopant material or a fluorescent dopant material.
  • the compound of formula 1 of the present invention may be included in the organic EL device as a blue, green, and / or red phosphorescent host, a fluorescent host, a hole transport material, a hole injection material and / or an electron transport material. More preferably, the compound of formula 1 of the present invention may be included in the organic EL device as a phosphorescent host or a fluorescent host, particularly preferably as a phosphorescent host.
  • the compound of the present invention has a high glass transition temperature of 150 °C or more, when the compound is used as an organic layer of the organic EL device, since the crystallization is minimized in the organic EL device, the driving voltage of the device can be lowered, luminous efficiency, luminance , Thermal stability, and lifetime characteristics can be improved.
  • a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode may be sequentially stacked, wherein the light emitting layer, hole injection layer, At least one of the hole transport layer and the electron transport layer may include a compound represented by Chemical Formula 1.
  • An electron injection layer may be positioned on the electron transport layer.
  • the organic EL device according to the present invention may not only have a structure in which an anode, at least one organic layer, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at the interface between the electrode and the organic layer.
  • the organic layer including the compound of Formula 1 may be formed by vacuum deposition or solution coating.
  • the solution application include spin coating, dip coating, doctor blading, inkjet printing or thermal transfer method, but is not limited thereto.
  • the organic EL device of the present invention forms an organic layer and an electrode using materials and methods known in the art, except that at least one of the organic layers is formed to include the compound represented by the formula (1) of the present invention. can do.
  • a silicon wafer, quartz, glass plate, metal plate, plastic film or sheet may be used as the substrate.
  • the anode material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT),
  • Cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer, the hole transport layer, the electron transport layer and the electron injection layer are not particularly limited, and conventional materials known in the art may be used.
  • Triphenylene 50 g, 219.0 mmol was dissolved in 750 ml of Chloroform and 51 ml (438.0 mmol) of Trimethyl phosphate, and the solution was heated and stirred at 60 ° C. in a nitrogen atmosphere.
  • Thianthren-1-ylboronic acid (10.2 g, 39.3 mmol), 15 g (58.9 mmol) of 1,3-Dibromo-5-fluorobenzene and Pd (PPh 3 ) 4 (0.45 g, 0.393 mmol) were placed in a flask and placed under a nitrogen atmosphere. After dissolving in a mixed solvent of 196 ml of toluene and 98 ml of ethanol, 98 ml of an aqueous solution of sodium carbonate (6.3 g, 58.9 mmol) was added thereto, followed by stirring under reflux for 12 hours.
  • Thianthren-1-ylboronic acid (11.3 g, 43.3 mmol), 2-Bromo-5-iodopyridine (14 g, 64.9 mmol) and Pd (PPh 3 ) 4 (0.50 g, 0.433 mmol) were placed in a flask and toluene under nitrogen atmosphere. After dissolving in a mixed solvent of 217 mL and 108 mL of ethanol, 108 mL of an aqueous solution of sodium carbonate (6.9 g, 64.9 mmol) was added thereto, and the mixture was stirred under reflux for 12 hours.
  • Thianthren-1-ylboronic acid (10.6 g, 40.6 mmol), 5-Bromo-2-chloropyrimidine (7.9 g, 40.6 mmol) and Pd (PPh 3 ) 4 (0.47 g, 0.406 mmol) were placed in a flask and toluene under nitrogen atmosphere. After dissolving in 203 mL, 102 mL of an aqueous solution of sodium carbonate (6.9 g, 64.9 mmol) was added thereto, followed by stirring under reflux for 12 hours.
  • Phenoxathiin-4-ylboronic acid (8.8g, 39.3mmol), 1-bromo-3-Iodobenzene (16.7 g, 58.9 mmol) and Pd (PPh 3 ) 4 (0.45 g, 0.393 mmol) were added to the flask and toluene under nitrogen atmosphere. After dissolving in a mixed solvent of 196 mL and 98 mL of Ethanol, 98 mL of an aqueous solution of Potassium carbonate (8.1 g, 58.9 mmol) was added thereto, followed by stirring under reflux for 12 hours.
  • Phenoxathiin-4-ylboronic acid (5.1 g, 22.58 mmol), 1,3,5-Tribromobenzene (7.1 g, 22.58 mmol) and Pd (PPh 3 ) 4 (0.26 g, 0.226 mmol) were added to the flask and toluene under nitrogen atmosphere. After dissolving in 151 mL, 75 mL of an aqueous solution of sodium carbonate (4.8 g, 45.2 mmol) was added thereto, followed by stirring under reflux for 12 hours.
  • Phenoxathiin-4-ylboronic acid (9.6 g, 39.3 mmol), 2,6-Dibromopyridine (14 g, 58.9 mmol), and Pd (PPh 3 ) 4 (0.45 g, 0.393 mmol) were placed in a flask and Toluene 196 under nitrogen atmosphere. After dissolving in a mixed solvent of ml and Ethanol 98 ml 98 ml of an aqueous solution of sodium carbonate (6.3 g, 58.9 mmol) was added and stirred under reflux for 12 hours.
  • Phenoxathiin-4-ylboronic acid (10.8 g, 43.3 mmol), 2-Bromo-5-iodopyridine (14 g, 64.9 mmol) and Pd (PPh 3 ) 4 (0.50 g, 0.433 mmol) were added to the flask and toluene under nitrogen atmosphere. After dissolving in a mixed solvent of 217 mL and 108 mL of ethanol, 108 mL of an aqueous solution of sodium carbonate (6.9 g, 64.9 mmol) was added thereto, and the mixture was stirred under reflux for 12 hours.
  • Phenoxathiin-4-ylboronic acid (9.9 g, 40.6 mmol), 5-Bromo-2-chloropyrimidine (7.9 g, 40.6 mmol) and Pd (PPh 3 ) 4 (0.47 g, 0.406 mmol) were placed in a flask and toluene under nitrogen atmosphere. After dissolving in 203 mL, 102 mL of an aqueous solution of sodium carbonate (6.9 g, 64.9 mmol) was added thereto, followed by stirring under reflux for 12 hours.
  • 1,2-dibromobenzene 50 g, 214 mmol
  • 3-methoxyphenylboronic acid (65.1 g, 428 mmol)
  • Pd (PPh 3 ) 4 (4.95 g, 4.28 mmol) were added to the flask and dissolved in 1.4 L of Toluene under nitrogen atmosphere.
  • 1.2 L of an aqueous solution of sodium carbonate (118.2 g, 856 mmol) was added thereto, and the mixture was stirred under reflux for 12 hours.
  • a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After washing with distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to the depositor.
  • ITO Indium tin oxide
  • An organic EL device was manufactured in the same manner as in Example 1, except that CBP was used as a light emitting host material, instead of the compound prepared in Synthesis Example, to form an emission layer.
  • Example 1-14 For each organic EL device manufactured in Example 1-14 and Comparative Example 1, the driving voltage, current efficiency, emission peak, and luminance at green light were measured, and the results are shown in Table 1 below.

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

Abstract

La présente invention porte sur des composés triphénylés et sur un dispositif électroluminescent organique les utilisant. Le composé de la présente invention a une excellente capacité d'injection et/ou de transfert de trous, et une excellente capacité de transfert d'électrons et/ou une luminosité, en particulier une luminosité dans le bleu et/ou le vert. Appliqué à des matériaux hôtes fluorescents ou phosphorescents, le dispositif électroluminescent organique peut améliorer des propriétés telles que le rendement de luminescence, la brillance, la tension de commande et la durée de vie.
PCT/KR2010/009508 2009-12-30 2010-12-29 Composés triphénylés, et dispositif électroluminescent organique les utilisant WO2011081451A2 (fr)

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JP2012079901A (ja) * 2010-09-30 2012-04-19 Fujifilm Corp 有機電界発光素子用材料、膜、発光層、有機電界発光素子、及び有機電界発光素子の製造方法
WO2014167286A3 (fr) * 2013-04-09 2015-02-19 Power Oleds Limited Composés hétérocycliques et leur utilisation dans des dispositifs électro-optiques ou opto-électroniques
EP2860783A1 (fr) * 2013-10-11 2015-04-15 Cheil Industries Inc. Dispositif opto-électronique organique et dispositif d'affichage
WO2015139808A1 (fr) 2014-03-18 2015-09-24 Merck Patent Gmbh Dispositif organique électroluminescent
JP2016092412A (ja) * 2014-10-31 2016-05-23 三星エスディアイ株式会社Ｓａｍｓｕｎｇ ＳＤＩ Ｃｏ．，Ｌｔｄ． 有機光電子素子および表示装置
GB2537195A (en) * 2013-04-09 2016-10-12 Power Oleds Ltd Heterocyclic compounds and their use in electro-optical or opto-electronic devices
WO2016173019A1 (fr) * 2015-04-29 2016-11-03 深圳市华星光电技术有限公司 Composé conjugué contenant une structure phénoxathiine, son procédé de préparation, et dispositif à diodes électroluminescents organiques
US20170170405A1 (en) * 2015-12-10 2017-06-15 Samsung Display Co., Ltd Organic light-emitting device
CN107325090A (zh) * 2016-04-12 2017-11-07 株式会社Lg化学 化合物及包含它的有机电子元件

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CN104795503B (zh) 2014-01-16 2018-07-20 三星显示有限公司 有机发光装置
WO2024101948A1 (fr) * 2022-11-11 2024-05-16 주식회사 엘지화학 Composé et élément électroluminescent organique le comprenant

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JP2006024898A (ja) * 2004-06-09 2006-01-26 Mitsubishi Chemicals Corp 正孔阻止材料及び有機電界発光素子
JP2006143845A (ja) * 2004-11-18 2006-06-08 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置
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Cited By (13)

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JP2012079901A (ja) * 2010-09-30 2012-04-19 Fujifilm Corp 有機電界発光素子用材料、膜、発光層、有機電界発光素子、及び有機電界発光素子の製造方法
GB2537195B (en) * 2013-04-09 2017-12-13 Power Oleds Ltd Heterocyclic compounds and their use in electro-optical or opto-electronic devices
WO2014167286A3 (fr) * 2013-04-09 2015-02-19 Power Oleds Limited Composés hétérocycliques et leur utilisation dans des dispositifs électro-optiques ou opto-électroniques
US10439147B2 (en) 2013-04-09 2019-10-08 Power Oleds Limited Heterocyclic compounds and their use in electro-optical or opto-electronic devices
JP2016523815A (ja) * 2013-04-09 2016-08-12 パワー オーエルイーディーズ リミテッドＰｏｗｅｒ Ｏｌｅｄｓ Ｌｉｍｉｔｅｄ 電光あるいは光電デバイスにおける複素環式化合物とその使用
GB2537195A (en) * 2013-04-09 2016-10-12 Power Oleds Ltd Heterocyclic compounds and their use in electro-optical or opto-electronic devices
EP2860783A1 (fr) * 2013-10-11 2015-04-15 Cheil Industries Inc. Dispositif opto-électronique organique et dispositif d'affichage
US10050212B2 (en) 2013-10-11 2018-08-14 Cheil Industries, Inc. Organic optoelectric device and display device
WO2015139808A1 (fr) 2014-03-18 2015-09-24 Merck Patent Gmbh Dispositif organique électroluminescent
JP2016092412A (ja) * 2014-10-31 2016-05-23 三星エスディアイ株式会社Ｓａｍｓｕｎｇ ＳＤＩ Ｃｏ．，Ｌｔｄ． 有機光電子素子および表示装置
WO2016173019A1 (fr) * 2015-04-29 2016-11-03 深圳市华星光电技术有限公司 Composé conjugué contenant une structure phénoxathiine, son procédé de préparation, et dispositif à diodes électroluminescents organiques
US20170170405A1 (en) * 2015-12-10 2017-06-15 Samsung Display Co., Ltd Organic light-emitting device
CN107325090A (zh) * 2016-04-12 2017-11-07 株式会社Lg化学 化合物及包含它的有机电子元件

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