WO2013133575A1 - Nouveau composé et élément électroluminescent organique le comprenant - Google Patents

Nouveau composé et élément électroluminescent organique le comprenant Download PDF

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WO2013133575A1
WO2013133575A1 PCT/KR2013/001640 KR2013001640W WO2013133575A1 WO 2013133575 A1 WO2013133575 A1 WO 2013133575A1 KR 2013001640 W KR2013001640 W KR 2013001640W WO 2013133575 A1 WO2013133575 A1 WO 2013133575A1
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김태형
김성무
백영미
김회문
박호철
신진용
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주식회사 두산
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Priority claimed from KR1020120024617A external-priority patent/KR101418146B1/ko
Priority claimed from KR1020120024619A external-priority patent/KR101434723B1/ko
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Publication of WO2013133575A1 publication Critical patent/WO2013133575A1/fr

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Definitions

  • the present invention relates to a novel compound and an organic electroluminescent device comprising the same, and more particularly to a compound used in the organic material layer of the organic electroluminescent device.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
  • the light emitting material may be classified into a light emitting material representing blue, green, and red according to the light emission color, and a light emitting material representing yellow and orange required to implement natural colors.
  • a host / dopant system may be used as the light emitting material.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound including Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 is used, and CBP is used as the phosphorescent host material.
  • the conventional light emitting materials have good light emission characteristics, they are not satisfactory in terms of lifespan of organic electroluminescent devices, and thus, development of light emitting materials having excellent performance is required.
  • an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.
  • the present invention provides a compound represented by the following formula (1).
  • X 1 to X 4 are each independently CR 1 or N, wherein at least one of X 1 to X 4 is N, X 1 and X 2 , or one of X 2 and X 3 is represented by the following formula (2) Combine with a compound to form a condensed ring,
  • the dotted line means a moiety combined with Formula 1 to form a condensed ring
  • Z is selected from the group consisting of CAr 2 Ar 3 , NAr 4 , O, S and SiAr 5 Ar 6 ,
  • Ar 1 to Ar 6 are each independently hydrogen, deuterium, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms aryl of from 5 to 60 heteroaryl group, a C 1 ⁇ alkyloxy group of C 40, C 6 ⁇ C 60 is selected from the group consisting of an aryloxy group, a C 1 to C 40 alkylsilyl group, a C 6 to C 60 arylsilyl group, and a C 6 to C 60 arylamine group, and combine with an adjacent group to form a condensed ring.
  • Y 1 to Y 8 are each independently CR 2 or N,
  • R 1 and R 2 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, the number of nuclear atoms of 3 to 40 of the heterocycloalkyl of the alkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 1 ⁇ alkyloxy group of C 40, C 6 and aryloxy C 60, C 1 ⁇ C 40 alkyl silyl group, C 6 to C 60 aryl silyl group, and a C 6 - is selected from the group consisting of an aryl amine of the C 60, the combined contiguous groups fused ring Can form,
  • arylamine groups are each independently deuterium, halogen, nitro group, cyano group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 Of cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 40 , heteroaryl group of 5 to 40 nuclear atoms, alkyloxy group of C 1 to C 40 , C 6 to C 60 It may be substituted with one or more selected from the group consisting of an aryloxy group, C 1 ⁇ C 40 Al
  • the substituents may be the same as or different from each other. That is, the plurality of substituents may be the same or different from each other.
  • Alkyl of the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, and non-limiting examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl , iso-amyl and hexyl.
  • Alkenyl of the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond.
  • Non-limiting examples thereof include vinyl, allyl, isopropenyl, 2-butenyl and the like.
  • Alkynyl of the present invention means a monovalent functional group obtained by removing a hydrogen atom from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond.
  • Non-limiting examples thereof include ethynyl, 2-propynyl and the like.
  • Cycloalkyl of the present invention means a monovalent functional group obtained by removing a hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms (saturated cyclic hydrocarbon).
  • Non-limiting examples thereof include cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine and the like.
  • Heterocycloalkyl of the present invention means monovalent functional groups obtained by removing hydrogen atoms from non-aromatic hydrocarbons (saturated cyclic hydrocarbons) having 3 to 40 nuclear atoms, and preferably at least one carbon in the ring, preferably 1 to 3 carbon atoms. Carbons are substituted with heteroatoms such as N, O or S. Non-limiting examples thereof include morpholine, piperazine and the like.
  • Aryl of the present invention means a monovalent functional group obtained by removing a hydrogen atom from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
  • the two or more rings may be attached in a simple or condensed form with each other.
  • Non-limiting examples thereof include phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, anthryl and the like.
  • Heteroaryl of the present invention is a monovalent functional group obtained by removing a hydrogen atom from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons. Is substituted with a heteroatom such as nitrogen (N), oxygen (O), sulfur (S) or selenium (Se).
  • the heteroaryl may be attached in a form in which two or more rings are simply attached or condensed with each other, and may also include a condensed form with an aryl group.
  • heteroaryls include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like.
  • the alkyloxy of the present invention means a monovalent functional group represented by RO-, wherein R is alkyl having 1 to 40 carbon atoms, and may include a linear, branched or cyclic structure.
  • R is alkyl having 1 to 40 carbon atoms, and may include a linear, branched or cyclic structure.
  • Non-limiting examples of such alkyloxy include methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Aryloxy of the present invention means a monovalent functional group represented by R'0-, wherein R 'is an aryl having 6 to 60 carbon atoms.
  • R ' is an aryl having 6 to 60 carbon atoms.
  • Non-limiting examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • Alkylsilyl of the present invention means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms
  • arylamine is amine substituted with aryl having 6 to 60 carbon atoms. Means.
  • Condensed ring of the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
  • the present invention comprises an anode, a 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 the formula (1) It provides an organic electroluminescent device.
  • novel compound of the present invention forms a basic skeleton by condensation (fused) heterocyclic moiety to an azacarbazole-based compound, and is a compound in which various substituents are bonded to the compound represented by Formula 1 above.
  • the compound represented by the formula (1) of the present invention is a compound containing one or more N (nitrogen) instead of C, carbon 1, 3 or 4 of the carbazole. That is, the compound represented by the formula (1) of the present invention is a compound represented by the following formula (3) or formula (4).
  • Ar 1 , X 1 , X 3 , X 4 , Y 1 to Y 8 and Z are the same as defined in Formula 1, at least one of X 1 , X 3 and X 4 is N It is preferable that it is (nitrogen).
  • Such a compound represented by Formula 1 of the present invention is a combination of a variety of substituents (R 1 , R 2 and Ar 1 to Ar 6 ) to control the energy level of a conventional organic electroluminescent device material (for example, CBP ( 4,4-dicarbazolybiphenyl)) has a higher molecular weight and may exhibit a wider energy band gap (sky blue to red).
  • a conventional organic electroluminescent device material for example, CBP ( 4,4-dicarbazolybiphenyl)
  • the compound represented by the formula (1) of the present invention in which various substituents are introduced the molecular weight is significantly increased, thereby improving the glass transition temperature, thereby having a higher thermal stability than the conventional materials.
  • the compound represented by Chemical Formula 1 of the present invention when used as a material of an organic electroluminescent device, not only phosphorescence properties of the device, but also electron and / or hole transporting ability, luminous efficiency, driving voltage, and lifetime characteristics may be improved.
  • the compound represented by Chemical Formula 1 of the present invention may be used as a material of the organic material layer of the organic EL device, preferably a hole injection layer, a hole transport layer or a light emitting layer, and more preferably a host material of the light emitting layer.
  • R 1 , R 2, and Ar 1 to Ar 6, which are substituents (functional groups) of the compound represented by Formula 1 of the present invention, may be any one of substituents represented by S1 to S138.
  • the compound represented by Chemical Formula 1 of the present invention may be selected from the group consisting of compounds represented by the following Chemical Formulas C-1 to C-30.
  • Z is preferably NAr 4 . That is, the compound represented by Formula 1 of the present invention contains one or more N (nitrogen) instead of A, acarbazole-based compound (C (carbon) 1, 3 or 4 of the carbazole of Formula 1) To an indole group of formula 2 (bonded to carbons 1 and 2 or carbons 2 and 3 of carbazole of formula 1).
  • the compound represented by Chemical Formula 1 of the present invention may be selected from the group consisting of compounds represented by the following Chemical Formulas D-1 to D-54.
  • Ar 1 and Ar 4 are each independently C 6 ⁇ C 60 An aryl group, a nuclear atom of 5 to 60 heteroaryl group, C 6 ⁇ it is selected from the group consisting of C 60 arylamine group, and a C 6 ⁇ C 60 aryl group in the silyl preferred.
  • Specific examples of the compound represented by Formula 1 of the present invention include the following compounds (1-1428), but is not limited thereto.
  • Such a compound represented by Formula 1 of the present invention can be synthesized in various ways with reference to the synthesis process of the following examples.
  • the present invention provides an organic electroluminescent device comprising an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is represented by Formula 1 described above. It is characterized by including the compound represented.
  • the organic material layer including the compound represented by Formula 1 of the present invention may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • the organic material layer of the present invention is preferably a hole injection layer, a hole transport layer or a light emitting layer, more preferably a light emitting layer.
  • the light emitting layer of the organic electroluminescent device of the present invention may contain a host material (preferably a phosphorescent host material).
  • a host material preferably a phosphorescent host material
  • the compound represented by Chemical Formula 1 may be used as the host material.
  • the organic light emitting diode since the hole transporting ability is increased to increase the bonding force between the holes and the electrons in the light emitting layer, the organic light emitting diode has excellent efficiency (emission efficiency and power efficiency), lifetime, luminance, driving voltage, and the like.
  • An electroluminescent device can be provided.
  • the structure of the organic electroluminescent device of the present invention is not particularly limited, but may be formed of a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode are sequentially stacked.
  • the electron injection layer may be further stacked on the electron transport layer.
  • the organic electroluminescent device of the present invention may have a structure in which an insulating layer or an adhesive layer is inserted between an electrode and an organic material layer.
  • the material that can be used as the anode included in the organic electroluminescent device of the present invention is not particularly limited, but non-limiting examples include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); A combination of a metal such as ZnO: Al or SnO 2 : Sb and the metal oxide; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black and the like can be used.
  • metals such as vanadium, chromium, copper, zinc, gold or alloys thereof
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); A combination of a metal such as ZnO: Al or SnO 2
  • the material that can be used as the cathode included in the organic electroluminescent device of the present invention is not particularly limited, but non-limiting examples include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin Or metals such as lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • the organic material layer included in the organic electroluminescent device of the present invention is in the art except that the compound represented by the formula (1) in any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer It may be made of known materials.
  • the material usable as the substrate included in the organic electroluminescent device of the present invention is not particularly limited, but non-limiting examples may be used a silicon wafer, quartz, glass plate, metal plate, plastic film and sheet.
  • Such an organic electroluminescent device of the present invention may be manufactured by a method known in the art, wherein the light emitting layer included in the organic material layer may be manufactured by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the procedure was followed to obtain 2- (2-nitrophenyl) -6- (3-nitropyridin-2-yl) pyrazine.
  • 3- (3-nitropyridin-2-yl) -9H-pyrido [2,3-b] indole is used instead of 2- (3-nitropyridin-2-yl) -5H-pyrazino [2,3-b] indole
  • 3- (3-nitropyridin-2-yl) -9-phenyl-9H-pyrido [2,3-b] indole was obtained by carrying out the same procedure as in ⁇ Step 3> of Preparation Example 7, except that.
  • IC-2 (2.27g, 8.86mmol), 1-bromobenzene (4.17g, 26.56mmol), Cu powder (0.11g, 1.77mmol), K 2 CO 3 (2.44g) as a compound prepared in Preparation Example 2 under nitrogen stream , 17.71 mmol), Na 2 SO 4 (2.52 g, 17.71 mmol) and nitrobenzene (100 ml) were mixed and stirred at 190 ° C. for 12 hours. After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound Mat-1 (2.35g, 65% yield).
  • IC-2 (1.48g, 5.76mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.69g, 13.8mmol), NaH (0.346g, 14.4mmol) and DMF (under nitrogen stream) 80 ml) was mixed and stirred at room temperature for 3 hours. After the reaction was completed, water was added, the solid compound was filtered and purified by column chromatography to obtain Mat-3 (2.94 g, yield 71%) as a target compound.
  • IC-2 (2.28g, 8.86mmol), 1-bromobenzene (4.17g, 26.56mmol), Cu powder (0.11g, 1.77mmol), K 2 CO 3 (2.44g) as a compound synthesized in Preparation Example 2 under nitrogen stream , 17.71 mmol), Na 2 SO 4 (2.52 g, 17.71 mmol), and nitrobenzene (100 ml) were mixed and stirred at 190 ° C. for 12 hours. After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 .
  • IC-2 (2.28g, 8.86mmol), 2-bromopyridine (4.19g, 26.56mmol), Cu powder (0.11g, 1.77mmol), K 2 CO 3 (2.44g) as a compound synthesized in Preparation Example 2 under nitrogen stream , 17.71 mmol), Na 2 SO 4 (2.52 g, 17.71 mmol), and nitrobenzene (100 ml) were mixed and stirred at 190 ° C. for 12 hours. After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the intermediate compound A-22 (1.95g, 66% yield).
  • IC-1 (2.28g, 8.86mmol), 4-bromobiphenyl (6.19g, 26.56mmol), Cu powder (0.11g, 1.77mmol), K 2 CO 3 (2.44g) as a compound synthesized in Preparation Example 1 under nitrogen stream , 17.71 mmol), Na 2 SO 4 (2.52 g, 17.71 mmol), and nitrobenzene (100 ml) were mixed and stirred at 190 ° C. for 12 hours. After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the intermediate compound A-26 (2.28g, 63% yield).
  • IC-8 (1.92g, 5.76mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.69g, 13.8mmol), NaH (0.346) as a compound prepared in Preparation Example 8 under nitrogen stream g, 14.4 mmol) and DMF (80 ml) were mixed and stirred at room temperature for 3 hours. After the reaction was completed, water was added, the solid compound was filtered and purified by column chromatography to obtain Mat-27 (2.57 g, yield 79%) as a target compound.
  • IC-8 (2.96g, 8.86mmol), 2-bromo-4,6-diphenylpyridine (3.27g, 10.6mmol), Cu powder (0.11g, 1.77mmol), K which is a compound prepared in Preparation Example 8 under nitrogen stream 2 CO 3 (2.44 g, 17.71 mmol), Na 2 SO 4 (2.52 g, 17.71 mmol) and nitrobenzene (100 ml) were mixed and stirred at 190 ° C. for 12 hours. After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound Mat-29 (2.99g, yield 60%).
  • IC-10 (1.48g, 5.76mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (3.69g, 13.8mmol), NaH (0.346) which is a compound prepared in Preparation Example 10 under nitrogen stream g, 14.4 mmol) and DMF (80 ml) were mixed and stirred at room temperature for 3 hours. After the reaction was completed, water was added, the solid compound was filtered and purified by column chromatography to obtain Mat-37 (3.10 g, yield 75%) as a target compound.
  • IC-11 (1.92g, 5.76mmol), 2-chloro-4,6-diphenyl-1,3,5-triazine (2.10g, 7.85mmol), NaH (compounds prepared in Preparation Example 11) under nitrogen stream 0.211 g, 8.78 mmol) and DMF (80 ml) were mixed and stirred at room temperature for 3 hours. After the reaction was completed, water was added, and the solid compound was filtered and purified by column chromatography to obtain Mat-52 (2.30 g, yield 71%) as a target compound.
  • an ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol, etc.
  • UV OZONE cleaner Power sonic 405, Hwasin Tech
  • M-MTDATA 60 nm) / TCTA (80 nm) / Mat-1 to Mat-66 compound + 10% Ir (ppy) 3 (300nm) / BCP (10 nm) / Alq 3 on the thus prepared ITO transparent substrate (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to manufacture a device.
  • a green organic electroluminescent device was manufactured in the same manner as in Example 1, except for using the following CBP instead of the compound Mat-1 as a light emitting host material when forming the light emitting layer.
  • a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that Com-1, instead of Compound Mat-1, was used as a light emitting host material when forming the emission layer.
  • Example 1 Host Drive voltage (V) Emission Peak (nm) Current efficiency (cd / A) Example 1 Mat-1 6.65 515 40.5 Example 2 Mat-2 6.60 518 41.0 Example 3 Mat-3 6.69 519 40.8 Example 4 Mat-4 6.51 515 40.7 Example 5 Mat-5 6.50 518 40.8 Example 6 Mat-6 6.60 515 39.7 Example 7 Mat-7 6.50 520 41.0 Example 8 Mat-8 6.63 517 40.1 Example 9 Mat-9 6.48 516 40.4 Example 10 Mat-10 6.40 518 41.0 Example 11 Mat-11 6.60 519 40.7 Example 12 Mat-12 6.50 518 41.1 Example 13 Mat-13 6.70 515 40.2 Example 14 Mat-14 6.55 518 40.4 Example 15 Mat-15 6.45 515 41.0 Example 16 Mat-16 6.59 519 41.5 Example 17 Mat-17 6.66 518 39.9 Example 18 Mat-18 6.56 516 41.5 Example 19 Mat-19 6.60 518 40.8 Example 20 Mat-20 6.52 517 41.3 Example 21 Mat-21 6.70 515 40.3 Example 22 Mat-22 6.51 517 41.0 Example 23 Mat-23 6.
  • Compound represented by Formula 1 of the present invention can be applied to the organic material layer of the organic electroluminescent device because of its excellent thermal stability and phosphorescence properties.
  • the compound represented by Formula 1 of the present invention when used as a phosphorescent host material of the light emitting layer among the organic material layers, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency and long life can be manufactured, and furthermore, performance, lifetime This greatly improved full color display panel can also be manufactured.

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

Abstract

La présente invention concerne un composé ayant une structure de squelette formée par liaison d'un composé à base d'azacarbazole à une fraction hétérocyclique condensée, et divers substituants liés à celle-ci, et un élément électroluminescent organique comprenant le composé. La présente invention peut fournir un élément électroluminescent organique ayant des rendement, durée de vie, stabilité améliorés et similaires.
PCT/KR2013/001640 2012-03-09 2013-02-28 Nouveau composé et élément électroluminescent organique le comprenant WO2013133575A1 (fr)

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KR1020120024617A KR101418146B1 (ko) 2012-03-09 2012-03-09 신규 화합물 및 이를 포함하는 유기 전계 발광 소자
KR10-2012-0024617 2012-03-09
KR1020120024619A KR101434723B1 (ko) 2012-03-09 2012-03-09 신규 화합물 및 이를 포함하는 유기 전계 발광 소자
KR10-2012-0024619 2012-03-09

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KR20150052705A (ko) * 2013-11-06 2015-05-14 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
JP2018090543A (ja) * 2016-12-05 2018-06-14 株式会社日本触媒 縮合多環式化合物の製造方法
CN109980112A (zh) * 2017-12-27 2019-07-05 三星Sdi株式会社 组合物、有机光电子装置及显示装置
CN112341460A (zh) * 2020-11-04 2021-02-09 浙江华显光电科技有限公司 一种有机化合物及使用该化合物的有机发光器件
CN113321659A (zh) * 2021-05-27 2021-08-31 武汉尚赛光电科技有限公司 一种有机电致发光材料及其器件
CN114716363A (zh) * 2022-05-07 2022-07-08 河南驼人医疗器械研究院有限公司 一种含羟基新型吡啶类季铵盐化合物及其合成方法和其在纤维抗菌改性中的应用

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KR20110122129A (ko) * 2009-01-20 2011-11-09 메르크 파텐트 게엠베하 유기 전계발광 소자용 재료
KR20110129767A (ko) * 2010-05-26 2011-12-02 덕산하이메탈(주) 헤테로 원자를 포함하는 카바졸과 플루오렌이 융합된 화합물 및 이를 이용한 유기전기소자, 그 단말
KR20110134923A (ko) * 2009-03-31 2011-12-15 신닛테츠가가쿠 가부시키가이샤 인광 발광 소자용 재료 및 이것을 사용한 유기 전계 발광 소자

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US20110062429A1 (en) * 2008-05-08 2011-03-17 Takahiro Kai Compound for organic electroluminescent device and organic electroluminescent device
KR20110122129A (ko) * 2009-01-20 2011-11-09 메르크 파텐트 게엠베하 유기 전계발광 소자용 재료
KR20110134923A (ko) * 2009-03-31 2011-12-15 신닛테츠가가쿠 가부시키가이샤 인광 발광 소자용 재료 및 이것을 사용한 유기 전계 발광 소자
KR20110129767A (ko) * 2010-05-26 2011-12-02 덕산하이메탈(주) 헤테로 원자를 포함하는 카바졸과 플루오렌이 융합된 화합물 및 이를 이용한 유기전기소자, 그 단말

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150052705A (ko) * 2013-11-06 2015-05-14 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR101603387B1 (ko) * 2013-11-06 2016-03-14 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
JP2018090543A (ja) * 2016-12-05 2018-06-14 株式会社日本触媒 縮合多環式化合物の製造方法
CN109980112A (zh) * 2017-12-27 2019-07-05 三星Sdi株式会社 组合物、有机光电子装置及显示装置
CN109980112B (zh) * 2017-12-27 2021-07-30 三星Sdi株式会社 组合物、有机光电子装置及显示装置
CN112341460A (zh) * 2020-11-04 2021-02-09 浙江华显光电科技有限公司 一种有机化合物及使用该化合物的有机发光器件
CN113321659A (zh) * 2021-05-27 2021-08-31 武汉尚赛光电科技有限公司 一种有机电致发光材料及其器件
CN114716363A (zh) * 2022-05-07 2022-07-08 河南驼人医疗器械研究院有限公司 一种含羟基新型吡啶类季铵盐化合物及其合成方法和其在纤维抗菌改性中的应用

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