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WO2015111942A2 - Composé organique et élément électroluminescent organique le contenant - Google Patents

Composé organique et élément électroluminescent organique le contenant Download PDF

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WO2015111942A2
WO2015111942A2 PCT/KR2015/000699 KR2015000699W WO2015111942A2 WO 2015111942 A2 WO2015111942 A2 WO 2015111942A2 KR 2015000699 W KR2015000699 W KR 2015000699W WO 2015111942 A2 WO2015111942 A2 WO 2015111942A2
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group
synthesis
mol
indole
bromo
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WO2015111942A3 (fr
Inventor
엄민식
김회문
박성진
이창준
신진용
김태형
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Doosan Corp
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Doosan Corp
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Definitions

  • the present invention relates to an organic compound and an organic electroluminescent device comprising the same.
  • the organic electroluminescent device when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine.
  • the material included in 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 blue, green, and red light emitting materials according to the light emitting color, and yellow and orange light emitting materials required to realize a better natural color.
  • a host / dopant system may be used as a light emitting material to increase luminous efficiency through an increase in color purity and energy transfer.
  • 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.
  • anthracene derivatives are known as fluorescent dopant / host materials used in the light emitting layer.
  • a phosphorescent dopant material used in the light emitting layer metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 are known, and as a phosphorescent host material, 4,4-dicarbazolybiphenyl (CBP) is known.
  • the existing materials are not satisfactory in terms of lifespan of the organic EL device due to low thermal stability due to low glass transition temperature, and still need improvement in terms of emission characteristics.
  • an object of the present invention is to provide an organic compound having a high glass transition temperature and excellent thermal stability and luminescence properties.
  • an object of this invention is to provide the organic electroluminescent element containing the said organic compound.
  • the present invention provides a compound represented by the following formula (1).
  • X 1 is selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ),
  • X 2 and X 3 are each independently N or C (R 2 ),
  • Y 1 to Y 4 are each independently N or C (R 1 ), and at least one of Y 1 and Y 2 , Y 2 and Y 3, and Y 3 and Y 4 forms a condensed ring represented by Formula 2 below. and,
  • Dotted line is a portion that is bonded to the compound of Formula 1,
  • X 4 is selected from the group consisting of O, S, Se, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ),
  • Y 5 to Y 8 are each independently N or C (R 3 ),
  • At least one of X 1 and X 4 is N (Ar 1 ),
  • R 1 to R 3 and Ar 1 to Ar 5 are each independently, hydrogen, deuterium, halogen group, nitro group, amino group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 to 60 heteroaryl group, C 1 to C 40 Alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 the arylboronic group, C 1 ⁇ C 40 of the phosphine group, is selected from the group consisting of an aryl amine of the C 1 ⁇ C 40 phosphine oxide group, and a C 6 ⁇ C 60 of the,
  • R 1 to R 3 form or not form a condensed ring with an adjacent group
  • Alkyl boron group, aryl boron group, phosphine group, phosphine oxide group and arylamine group are each independently deuterium, halogen group, nitro 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 Cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 6 ⁇ C 60 Aryl group, Nuclear atoms 5 to 60 heteroaryl group, C 1 -C 40 alkyloxy group, C 6 -C 60 aryloxy group, C 1
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device comprising.
  • Alkyl in the present invention means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • Alkenyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • Alkynyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, and the like.
  • Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms combined with a single ring or two or more rings. It may also include a form in which two or more rings are attached to each other (pendant) or condensed. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom such as N, O, S or Se.
  • a form in which two or more rings are attached to each other (pendant) or condensed may also be included, and may also include a form condensed with an aryl group.
  • heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carbazolyl and 2-furanyl, N-imidazolyl, 2-isoxazolyl , 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, phenoxathienyl, indolinzinyl, indolyl ( polycyclic rings such as indolyl, purinyl, quinolyl, benzothiazole, carb
  • Aryloxy in the present invention is a monovalent substituent represented by RO-, wherein R means aryl having 6 to 60 carbon atoms.
  • R means aryl having 6 to 60 carbon atoms.
  • Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
  • Alkyloxy in the present invention is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, and a linear, branched or cyclic structure It may include.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons is N, O, S or Substituted with a hetero atom such as Se.
  • heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • Alkylsilyl in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 60 carbon atoms.
  • the condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the organic compound of the present invention is a structure in which two indene moieties containing one or more heteroatoms such as N, O, and S are fused to each other to form a basic skeleton, and various substituents are bonded to each other. Is displayed.
  • the host In the phosphorescent layer of the organic EL device, the host should have a triplet energy gap higher than that of the dopant. That is, in order to effectively provide phosphorescence from the dopant, the energy of the lowest excited state of the host must be higher than the energy of the lowest emission state of the dopant.
  • the compound represented by Formula 1 may exhibit a higher energy level than the dopant when used as a host because a specific substituent is introduced into the indene moiety having a wide singlet energy level and a high triplet energy level.
  • the compound represented by the formula (1) of the present invention includes at least one or more C 6 ⁇ C 60 aryl group substituted with a cyano group or at least one heteroaryl group having 5 to 60 nuclear atoms substituted with a cyano group Since it has a bipolar characteristic, when the host is used, the binding force between the holes and the electrons in the emission layer may be increased.
  • the compound represented by Chemical Formula 1 of the present invention prevents the excitons generated in the light emitting layer from diffusing to the adjacent electron transport layer or the hole transport layer, thereby increasing the number of excitons that contribute to the light emission, so that the light emission efficiency when used in the light emitting auxiliary layer In addition, the life of the organic EL device can be improved.
  • the compound represented by the general formula (1) of the present invention exhibits a high glass transition temperature by introducing various substituents, especially aryl groups and / or heteroaryl groups, thereby significantly increasing the molecular weight of the compound. , CBP) can have better thermal stability.
  • the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer.
  • the performance and lifespan characteristics of the organic EL device may be greatly improved.
  • the lifespan of the organic EL device may maximize the performance of the full color OLED panel.
  • Such a compound represented by Formula 1 of the present invention may be embodied as a compound represented by the following formula (1a to 1f).
  • Y 1 to Y 4 are N or C (R 1 ), all of which are preferably C (R 1 ), and Y 5 to Y 8 are N or C (R 3 ), all of which are C that the (R 3) are preferred.
  • R 1 and R 3 are the same or different from each other.
  • the compound represented by Chemical Formula 1 of the present invention may be further embodied by the compounds represented by the following Chemical Formulas B-1 to B-30, but is not limited thereto.
  • Ar 1 and R 1 to R 3 are the same as defined in Formula 1.
  • a plurality of R 1 is the same or different from each other
  • a plurality of R 2 is the same or different from each other
  • a plurality of R 3 is the same or different from each other.
  • R 1 to R 3 and Ar 1 to Ar 5 are each independently hydrogen, deuterium, a halogen group, a nitro group, an amino group, an alkyl group of C 1 to C 40 , and C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to the 60 heteroaryl group, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 groups of an alkyl boron, an aryl boronic of C 6 ⁇ C 60, C 1 ⁇ C 40 phosphine group, C 1 ⁇ C 40 phosphine oxide group, and
  • R 1 to R 3 are each independently hydrogen, halogen, cyano group, C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, nuclear atoms 5 to 60 heteroaryl group and C 6 ⁇ C It is preferably selected from the group consisting of 60 arylamine groups,
  • Ar 1 to Ar 5 are each independently composed of a C 6 ⁇ C 60 aryl group, a heteroaryl group of 5 to 60 nuclear atoms, a C 6 ⁇ C 60 arylamine group and a C 6 ⁇ C 60 arylsilyl group It is preferably selected from the group.
  • R 1 to R 3 and Ar 1 to Ar 5 is a C 6 ⁇ C 60 aryl group substituted with a cyano group or a heteroaryl group having 5 to 60 nuclear atoms substituted with a cyano group
  • Ar 1 is a C 6 to C 60 aryl group substituted with a cyano group or a heteroaryl group having 5 to 60 nuclear atoms substituted with a cyano group.
  • R 1 to R 3 and Ar 1 to Ar 5 may each independently be selected from hydrogen or a substituent consisting of S1 to S204, or a substituent including one or more cyano groups in the selected substituent (bonded) have.
  • the compound represented by the formula (1) of the present invention can be synthesized in various ways with reference to the following synthesis examples.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).
  • the present invention includes an anode, a cathode and at least one organic material layer interposed between the anode and the cathode, at least one of the organic material layer comprises an organic electric field comprising at least one compound represented by the formula (1)
  • a light emitting device Provided is a light emitting device.
  • the organic material layer including the compound represented by Chemical Formula 1 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 compound represented by Formula 1 may be included in the organic electroluminescent device as a light emitting layer material.
  • the organic EL device may improve luminous efficiency, brightness, power efficiency, thermal stability, and device life.
  • the compound represented by Formula 1 of the present invention is preferably a phosphorescent host, a fluorescent host or a dopant material of the light emitting layer, and more preferably a phosphorescent host material of the light emitting layer.
  • the structure of the organic EL device of the present invention is not particularly limited, but 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.
  • An electron injection layer may be inserted on the electron transport layer.
  • An insulating layer or an adhesive layer may be inserted between the electrode and the organic material layer interface.
  • the organic material layer including the compound represented by Chemical Formula 1 may be formed 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 organic electroluminescent device of the present invention may be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the compound represented by Chemical Formula 1. have.
  • a silicon wafer, a quartz or glass plate, a metal plate, a plastic film, or the like 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 metals and oxides 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 may be used, but is not limited thereto.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof;
  • a multilayer structure material such as LiF / Al or LiO 2 / Al may be used, but is not limited thereto.
  • the material used as the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited as long as it is a conventional material known in the art.
  • PC-2 was obtained by the same procedure as in ⁇ Step 4> of Preparation Example 1 using 5- (2-nitrophenyl) -1-phenyl-1H-indole, triphenylphosphine and 1,2-dichlorobenzene.
  • 6- (4,4,5,5-tetramethyl- obtained in ⁇ Step 1> instead of 5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-indole Except for using 1,3,2-dioxaborolan-2-yl) -1H-indole, 6- (2-nitrophenyl) -1H-indole was prepared in the same manner as in ⁇ Step 2> of Preparation Example 1. Got it.
  • 6-chloro-1H-indole 25 g, 0.17 mol
  • bromobenzene 31.19 g, 0.20 mol
  • Pd (OAc) 2 (1.86 g, 5 mol)
  • Triphenylphosphine (2.17 g, 5 mol%)
  • K 2 CO 3 68.64 g, 0.50 mol
  • 1,4-dioxane 300 ml
  • 6-bromo-1H-indazole instead of 5-bromo-1H-indazole, 6- (4,4,5,5-tetramethyl- was carried out in the same manner as in ⁇ Step 1> of Preparation Example 14 above. 1,3,2-dioxaborolan-2-yl) -1H-indazole was obtained.
  • 6- (2-nitrophenyl) -1H-indazole instead of 5- (2-nitrophenyl) -1H-indazole, 6- (2- nitrophenyl) -1-phenyl-1H-indole was obtained.
  • N- (2,4-dibromophenyl) benzamide 251.1 g, 710 mmol
  • K 2 CO 3 (196.3 g, 1420 mmol)
  • DMSO 7100 ml
  • 6-bromo-2-phenylbenzo [d] oxazole (147.9 g, 540.0 mmol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi under nitrogen stream (1,3,2-dioxaborolane) (150.8 g, 594.0 mmol), Pd (dppf) Cl 2 (62.4 g, 54.0 mmol), KOAc (152.5 g, 1.62 mol) and 1,4-Dioxane (2800 ml) Mix and stir at 130 ° C. for 12 h.
  • 6-bromo-2-phenylbenzo [d] thiazole (156.6 g, 540.0 mmol), 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi under nitrogen stream (1,3,2-dioxaborolane) (150.8 g, 594.0 mmol), Pd (dppf) Cl 2 (62.4 g, 54.0 mmol), KOAc (152.5 g, 1.62 mol) and 1,4-Dioxane (2800 ml) Mix and stir at 130 ° C. for 12 h.
  • PC-1 (3 g, 10.63 mmol), 3'-Bromo-biphenyl-4-carbonitrile (2.89 g, 11.20 mmol), Pd (OAc) 2 (0.12 g, 5 mol%), NaO (t-) under nitrogen stream bu) (2.04 g, 21.25 mmol), P (t-bu) 3 (0.21 g, 1.06 mmol) and Toluene (100 ml) were mixed and stirred at 110 ° C. for 12 h.
  • the target compound was prepared in the same manner as in Synthesis Example 1, except that PC-5 and 8-Bromo-dibenzothiophene-2-carbonitrile were used instead of PC-1 and 3'-Bromo-biphenyl-4-carbonitrile. 6 (3.28 g, 63%) was obtained.
  • Inv-9 (5.59 g, 75%) was obtained by the same procedure as in Synthesis Example 8, except that 9-phenyl-9H-carbazol-3-ylboronic acid was used instead of phenylboronic acid.
  • Inv-12 (3.32 g) was prepared by the same procedure as in Synthesis Example 1, except that PC-9 and 4-Bromo-benzonitrile were used instead of PC-1 and 3'-Bromo-biphenyl-4-carbonitrile. , 68%).
  • Inv-16 (3.47 g) was prepared by the same procedure as in Synthesis Example 1, except that PC-13 and 3-Bromo-benzonitrile were used instead of PC-1 and 3'-Bromo-biphenyl-4-carbonitrile. , 61%).
  • a target compound was prepared in the same manner as in Synthesis Example 1, except that IC-2 and 4'-Bromo-biphenyl-3-carbonitrile were used instead of PC-1 and 3'-Bromo-biphenyl-4-carbonitrile. -19 (4.01 g, 82%) was obtained.
  • a target compound was prepared in the same manner as in Synthesis Example 1, except that BOC-1 and 3'-Bromo-biphenyl-3-carbonitrile were used instead of PC-1 and 3'-Bromo-biphenyl-4-carbonitrile. -24 (3.53, 72%) was obtained.
  • a target compound was prepared in the same manner as in Synthesis Example 1, except that BOC-3 and 3'-Bromo-biphenyl-3-carbonitrile were used instead of PC-1 and 3'-Bromo-biphenyl-4-carbonitrile. -28 (4.29, 75%) was obtained.
  • a target compound was prepared in the same manner as in Synthesis Example 1, except that BTC-1 and 3'-Bromo-biphenyl-3-carbonitrile were used instead of PC-1 and 3'-Bromo-biphenyl-4-carbonitrile. -37 (3.81, 75%) was obtained.
  • a target compound was prepared in the same manner as in Synthesis Example 1, except that BTC-3 and 3'-Bromo-biphenyl-3-carbonitrile were used instead of PC-1 and 3'-Bromo-biphenyl-4-carbonitrile. -41 (4.47, 76%).
  • the compound synthesized in Synthesis Example was subjected to high purity sublimation purification by a conventionally known method, and the device was manufactured according to the following procedure.
  • a glass substrate coated with ITO Indium tin oxide
  • 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) / 90% Inv-1 to Inv-48 compound + 10% Ir (ppy) 3 (30 nm) / BCP (ITO transparent substrate (electrode) thus prepared) 10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to manufacture a device.
  • a device was manufactured in the same manner as in Example 1, except for using CBP instead of the compound Inv-1 as a light emitting host material when forming the emission layer.
  • Example 1 Sample Host Driving voltage (V) Light emitting peak (nm) Current efficiency (cd / A) Example 1 Inv-1 6.66 516 42.6 Example 2 Inv-2 6.91 517 39.4 Example 3 Inv-3 6.85 516 38.8 Example 4 Inv-4 6.86 516 43.5 Example 5 Inv-5 6.91 517 42.1 Example 6 Inv-6 6.85 516 42.6 Example 7 Inv-7 6.63 515 39.4 Example 8 Inv-8 6.75 515 38.8 Example 9 Inv-9 6.85 516 40.9 Example 10 Inv-10 6.63 517 42.1 Example 11 Inv-11 6.75 516 42.6 Example 12 Inv-12 6.73 517 39.4 Example 13 Inv-13 6.75 515 38.8 Example 14 Inv-14 6.63 516 40.9 Example 15 Inv-15 6.75 517 41.2 Example 16 Inv-16 6.73 516 39.2 Example 17 Inv-17 6.75 517 41.1 Example 18 Inv-18 6.81 517 42.0 Example 19 Inv-19 6.89 517 41.1 Example 20 Inv-20 6.81 518 4
  • the compound of the present invention has excellent thermal stability, electron and hole transport ability, light emitting ability, and the like, it can be usefully applied as an organic material layer material of an organic EL device.
  • the organic electroluminescent device including the compound of the present invention in the organic material layer can be effectively applied to a full color display panel since the aspects such as light emission performance, driving voltage, lifetime, and efficiency are greatly improved.

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  • Chemical & Material Sciences (AREA)
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  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
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Abstract

La présente invention concerne un composé organique et un élément électroluminescent organique le comprenant. Le composé organique de la présente invention est utilisé pour une couche de matériau organique, de préférence, une couche d'émission de lumière, de l'élément électroluminescent organique, et peut ainsi améliorer l'efficacité d'émission de lumière, la tension de commande, la durée de vie, et analogue, de l'élément électroluminescent organique.
PCT/KR2015/000699 2014-01-23 2015-01-23 Composé organique et élément électroluminescent organique le contenant Ceased WO2015111942A2 (fr)

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WO2023042814A1 (fr) * 2021-09-16 2023-03-23 株式会社Kyulux Composé, matériau électroluminescent et élément électroluminescent
CN116693550A (zh) * 2023-06-07 2023-09-05 浙江八亿时空先进材料有限公司 一种噁唑衍生物及其应用

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KR20170016701A (ko) * 2015-08-04 2017-02-14 주식회사 두산 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
WO2019164341A1 (fr) * 2018-02-23 2019-08-29 주식회사 엘지화학 Composé spiro et dispositif électroluminescent organique le comprenant
CN120398915A (zh) * 2020-12-14 2025-08-01 株式会社Lg化学 新的化合物和包含其的有机发光器件
CN120441591A (zh) * 2020-12-17 2025-08-08 株式会社Lg化学 新化合物和包含其的有机发光器件
WO2022131869A1 (fr) * 2020-12-17 2022-06-23 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant
KR102798817B1 (ko) * 2021-08-04 2025-04-23 주식회사 엘지화학 신규한 화합물 및 이를 포함한 유기 발광 소자

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KR20110066763A (ko) 2009-12-11 2011-06-17 덕산하이메탈(주) 인돌로아크리딘을 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말
WO2013085339A2 (fr) * 2011-12-07 2013-06-13 주식회사 두산 Composé électroluminescent organique et dispositif électroluminescent organique utilisant celui-ci
WO2013122364A2 (fr) * 2012-02-13 2013-08-22 덕산하이메탈(주) Composé pour élément électrique organique, élément électrique organique le comprenant et dispositif électronique avec celui-ci
KR102169443B1 (ko) * 2012-04-10 2020-10-23 에스에프씨 주식회사 이형고리 화합물 및 이를 포함하는 유기전계발광소자
KR101477344B1 (ko) * 2012-07-09 2014-12-29 주식회사 두산 신규 화합물 및 이를 포함하는 유기 전계 발광 소자
KR101507421B1 (ko) * 2012-07-12 2015-04-08 덕산네오룩스 주식회사 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

Cited By (2)

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WO2023042814A1 (fr) * 2021-09-16 2023-03-23 株式会社Kyulux Composé, matériau électroluminescent et élément électroluminescent
CN116693550A (zh) * 2023-06-07 2023-09-05 浙江八亿时空先进材料有限公司 一种噁唑衍生物及其应用

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