WO2016111515A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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Publication number
WO2016111515A1
WO2016111515A1 PCT/KR2016/000040 KR2016000040W WO2016111515A1 WO 2016111515 A1 WO2016111515 A1 WO 2016111515A1 KR 2016000040 W KR2016000040 W KR 2016000040W WO 2016111515 A1 WO2016111515 A1 WO 2016111515A1
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group
aryl
alkyl
host
boron
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PCT/KR2016/000040
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Korean (ko)
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엄민식
백영미
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주식회사 두산
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the present invention relates to an organic electroluminescent device comprising at least one organic material layer.
  • An organic electroluminescent device is a device in which holes are injected into an anode and electrons are injected into an organic material layer by applying a voltage between two electrodes. Excitons are formed when the injected holes and electrons meet, and light is generated when the excitons fall to the ground.
  • 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 hole injection material As the hole injection material, the hole transport material, and the electron transport material, NPB, BCP, Alq 3 and the like are known.
  • As the light emitting material anthracene derivative, Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 are known.
  • Metal complex compounds containing Ir and the like are known.
  • an object of the present invention is to provide an organic electroluminescent device comprising an organic compound capable of improving the driving voltage, current efficiency and lifespan of the organic electroluminescent device.
  • the present invention is an anode; 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 includes a first host and a second host, wherein the first host is represented by Formula 1 below.
  • R 1 to R 6 are the same or different and are each independently selected from the group consisting of hydrogen, deuterium, an alkyl group of C 1 to C 40 and an aryl group of C 6 to C 60 ,
  • a and f are each an integer of 0 to 5
  • b and e are each an integer of 0 to 4,
  • c and d are each an integer of 0 to 3
  • R a and R b are the same or different and each independently represent an alkyl group of C 1 to C 40 or an aryl group of C 6 to C 60 , or combine with each other to form a condensed ring,
  • R 7 to R 9 are the same or different, each independently represent hydrogen, deuterium, halogen group, cyano group, nitro group, amino group, C 1 ⁇ alkenyl group of the C 40 alkyl group, C 2 ⁇ C 40 of, 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, C 1 ⁇ C 40 phosphine oxide group, and a C 6 ⁇ selected from the group consisting of an aryl amine of the
  • L is selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms,
  • Z 1 to Z 5 are the same or different and each independently N or C (R 10 ), wherein at least one is N, and when there are a plurality of C (R 10 ), a plurality of R 10 are the same or different,
  • g, h and i are each an integer of 0 to 4,
  • n are each an integer of 1 to 3
  • R 10 is hydrogen, deuterium, halogen group, cyano 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 Of cycloalkyl group, heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of C 1 to C 40 , C 6 to 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 aryl boron group, C 1 ⁇ C 40 A phosphine group, a C 1 to C 40 phosphine oxide group and a C 6 to C 60 arylamine group, or combine with adjacent groups (specifically, adjacent R 10 bonds) to
  • the alkyl group and aryl group of R a and R b are each independently deuterium, halogen group, cyano group, nitro group , Amino group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C Aryl group of 6 to C 60 , heteroaryl group of 5 to 60 nuclear
  • the organic electroluminescent device of the present invention by applying the compound represented by Chemical Formula 1 as the first host and the compound represented by Chemical Formula 2 as the second host to the organic material layer, driving voltage, current efficiency, and lifetime may be improved. . Accordingly, the organic electroluminescent device can provide a display panel with improved performance and lifespan.
  • the organic electroluminescent device of the present invention is an anode; 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 includes a first host and a second host, wherein the first host is represented by Formula 1
  • the second host is a compound represented by Chemical Formula 2, which will be described in detail below.
  • the anode included in the organic EL device of the present invention serves to inject holes into the organic material layer.
  • Such an anode material is not particularly limited, but 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 or polyaniline; And carbon black and the like can be used.
  • the cathode included in the organic EL device of the present invention serves to inject electrons into the organic material layer.
  • a negative electrode material is not particularly limited, but a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • At least one organic material layer included in the organic electroluminescent device of the present invention may be any one or more of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emitting layer, a life improvement layer, an electron transport layer and an electron injection layer, at least one of
  • the organic layer may include a first host and a second host.
  • the organic material layer including the first host and the second host is preferably a light emitting layer or a light emitting auxiliary layer.
  • the light emitting layer included in the organic material layer of the present invention combines the first host and the second host by the injected holes and electrons to generate an exciplex, which is an excited state charge transfer complex.
  • the compound used as the first host in the present invention is a compound forming a structure in which an aromatic ring (specifically, a phenyl group) is bonded to the nitrogen atom of the biscarbazole moiety, respectively, represented by Chemical Formula 1.
  • the biscarbazole moiety has a high hole transport property due to a structure including two carbazole moieties having an electron donating group (EDG) characteristic having high electron donating and hole transporting properties.
  • EDG electron donating group
  • the biscarbazole moiety has a significantly higher molecular weight than the one carbazole moiety and has high thermal stability. These biscarbazole moieties may be firmly connected to two carbazole moieties due to the 3,3 ′ bond, thereby enhancing the thermal / electrical stability of the molecule itself.
  • the compound represented by Formula 1 of the present invention has an enhanced electron donor group (EDG) properties in the molecule while being bonded to an alkyl or aryl group having electron donating and hole transporting properties.
  • EDG enhanced electron donor group
  • R 1 to R 6 are the same or different, and are each independently hydrogen, methyl, ethyl, propyl, iso-propyl, t-butyl, phenyl and biphenyl group It is preferable to select, and it is more preferable that it is a phenyl group or a biphenyl group.
  • the compound represented by Chemical Formula 1 of the present invention may be more specific with the following compounds (A-1 to A-52), but is not limited thereto.
  • the compound used as the second host in the present invention is a compound consisting of a basic skeleton of a structure in which a fluorene moiety and a 6-membered heterocyclic ring are bonded by a linker group (phenyl or biphenyl), represented by Chemical Formula 2 do.
  • the fluorene moiety has an electron donor (EDG) characteristic of high electron donation.
  • EDG electron donor
  • a fluorene moiety is bound to a six-membered heterocycle (e.g., pyridine group, pyrimidine group, triazine group, etc.) which is an electron withdrawing group (EWG) having high electron absorption by a linker group, the whole molecule
  • EWG electron withdrawing group
  • the compound represented by Formula 2 of the present invention may be embodied as any one of the compounds represented by the following Formulas 3 to 5, but is not limited thereto.
  • R a , R b , R 7 to R 9 , Z 1 to Z 5 , g, h and i are the same as defined in Chemical Formula 2, respectively.
  • R a and R b are the same or different, and each independently a methyl group or a phenyl group, or combine with each other It is preferable to form a condensed ring represented by (* is a site
  • R 7 to R 9 are the same or different, and each independently hydrogen, deuterium, an alkyl group of C 1 to C 40 , an aryl group of C 6 to C 60 , a heteroaryl group of 5 to 60 nuclear atoms, and C 6 to It is preferably selected from the group consisting of C 60 arylamine groups.
  • M and n are each an integer of 1 to 3, m is preferably 1, and n is preferably 1 or 2.
  • said L is a single bond, a phenylene group, or a biphenylene group.
  • the part (substituent) represented by (* is a site where a bond is formed with L) may be embodied as any one of structures (substituents) represented by the following C-1 to C-15, but is not limited thereto.
  • R 10 is as defined in Formula 2,
  • R 11 is 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, aryloxy nuclear atoms 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 6 ⁇ C 60, alkyloxy group of C 1 ⁇ C 40 , C 6 ⁇ C 60 arylamine group, C 1 ⁇ C 40 alkylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group , C 6 ⁇ C 60 aryl phosphine oxide group and C 6 ⁇ C 60 arylsilyl group, or combine with adjacent groups (
  • p is an integer from 1 to 4,
  • the arylphosphine group, the arylphosphine oxide group and the arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alky Neyl group, C 6 ⁇ C 60 aryl group, C 5 ⁇ C 60 heteroaryl group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 Alkyloxy group, C 6 ⁇ C 60 arylamine aryl boron group,
  • the compound represented by Formula 2 of the present invention may be embodied by the following compounds (B-1 to B-173), but is not limited thereto.
  • alkyl is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms.
  • alkyl include methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • Alkenyl in the present invention is 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.
  • alkenyl include vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • Alkynyl in the present invention is 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.
  • alkynyl include 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.
  • a form in which two or more rings are attached to each other (pendant) or condensed may also be included.
  • aryls include 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 pendant or condensed with each other 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, 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, etc. are mentioned.
  • Aryloxy in the present invention is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include phenyloxy, naphthyloxy, diphenyloxy and the like.
  • Alkyloxy in the present invention is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and includes a linear, branched or cyclic structure It is interpreted as. Examples of such alkyloxy include 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 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. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a hetero atom such as N, O, S or Se. Examples of such heterocycloalkyl include morpholine, piperazine and the like.
  • Alkylsilyl in the present invention means silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 5 to 40 carbon atoms.
  • Condensed ring in 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 organic electroluminescent device to which the first host and the second host are applied can have a high lifetime since the holes and electrons can be balanced.
  • the mixing ratio of the first host and the second host is not particularly limited, but it is preferable that the first host and the second host are mixed in a weight ratio of 1:99 to 99: 1, and 25:75 It is more preferable to mix in a weight ratio of 75 to 25:25.
  • a plurality of light emitting layers may be sequentially stacked between the hole transporting layer and the electron transporting layer to implement a mixed color thereof when voltage and current are applied, and the light emitting efficiency may be increased by the number of light emitting layers.
  • the light emitting layer of the present invention may include a metal complex compound-based dopant together with the first host and the second host.
  • the method of manufacturing the light emitting layer of the present invention is not particularly limited, but non-limiting examples include a co-deposition method, a vacuum deposition method, a solution coating method and the like.
  • a light emitting layer is manufactured by disposing a first host and a second host in a first heat source and a second heat source, and placing a dopant in a third heat source and simultaneously applying heat to co-deposit.
  • a first host having high hole mobility and good hole injection efficiency is disposed in the first heat source, and has high electron mobility and electron injection.
  • the efficient second host is disposed in the second heat source, the dopant is disposed in the third heat source, and then co-deposition is performed at an appropriate ratio by simultaneously controlling the evaporation rate of each material at the same time.
  • the number of co-deposited hosts may be two or more according to the characteristics of the light emitting layer.
  • the amount of the first host, the second host and the dopant is not particularly limited in manufacturing the light emitting layer, but it is preferable to use the mixed first host and the second host at 70 to 99 wt% and the dopant at 1 to 30 wt%. It is more preferable to use 80 to 95% by weight of the mixed first host and the second host and 5 to 20% by weight of the dopant.
  • the light emitting layer may be manufactured by mixing hosts having similar deposition temperatures in the host at an appropriate ratio, placing them in one heat source, and co-depositing by applying heat.
  • a host (first host + second host) mixed in the first heat source at a vacuum degree of 1 ⁇ 10 ⁇ 06 or less, a dopant is disposed in the second heat source, and the evaporation rate per second of each material is simultaneously It is adjusted to prepare a light emitting layer.
  • the light emitting layer when the light emitting layer is manufactured by disposing a host mixed with the first heat source, an error of one or more host mixing ratios can be reduced, and the light emitting layer can be formed using a small number of heat sources. Specifically, when the deposition temperature of the first host and the second host is ⁇ 10 °C can be mixed and placed in one heat source.
  • the amount of the first host, the second host and the dopant is not particularly limited in manufacturing the light emitting layer, but it is preferable to use 70 to 99% by weight of the mixed first host and the second host and 1 to 30% by weight of the dopant. It is more preferable to use 80-95 wt% of the mixed first host and the second host and 5-20 wt% of the dopant.
  • the structure of the organic EL device of the present invention is not particularly limited, but may be a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, an emission auxiliary layer, a light emitting layer, a life improvement layer, an electron transport layer, and a cathode are sequentially stacked.
  • an electron injection layer may be further stacked on the electron transport layer.
  • an insulating layer or an adhesive layer may be further stacked on an interface between the electrode (cathode or anode) and the organic material layer.
  • the substrate used in the manufacture of the organic EL device of the present invention is not particularly limited, but a silicon wafer, quartz, glass plate, metal plate, plastic film, or the like can be used.
  • the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and conventional materials known in the art may be used.
  • II-1 (11.0 g, 0.026 mol), 9,9-Dimethyl-9H-fluoren-2-yl-boronic acid (7.9 g, 0.033 mol) obtained in ⁇ Step 1> of Synthesis Example 12, Pd ( OAc) 2 (0.58 g, 2.6 mmol), XPhos (2.5 g, 5.2 mmol) and Cesium carbonate (16.9 g, 0.052 mol) were mixed, followed by Toluene (200 mL), Ethanol (100 mL) and H 2 O ( 50 mL) at reflux.
  • an organic electroluminescent device was manufactured as follows.
  • the glass substrate coated with ITO Indium tin oxide having a thickness of 1500 mm 3 was ultrasonically cleaned with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwashin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • the structures of m-MTDATA, TCTA, Ir (ppy) 3 and BCP used are as follows, and the mixing ratio of host A and host B is 50:50.
  • Example 1 On the prepared ITO transparent substrate (electrode), compound (A-11) synthesized in Synthesis Example 4 was used as a host A, and compound (B-1) synthesized in Synthesis Example 8 was used as a host B, and m-MTDATA ( 60 nm) / TCTA (80 nm) / 90% A-11 and B-1 + 10% Ir (ppy) 3 (30 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to manufacture an organic EL device.
  • m-MTDATA 60 nm) / TCTA (80 nm) / 90% A-11 and B-1 + 10% Ir (ppy) 3 (30 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) was laminated in order to manufacture an organic EL device.
  • An organic EL device was manufactured in the same manner as in Example 1, except that 90% CBP + 10% Ir (ppy) 3 was used to form the emission layer.
  • the structure of the CBP used is as follows.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that 90% of Com-1 + 10% Ir (ppy) 3 was used to form the emission layer.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that 90% of A-11 + 10% of Ir (ppy) 3 was used to form the emission layer.
  • Example 1 50% A-2 + 50% B-1 5.12 45.8
  • Example 2 50% A-2 + 50% B-3 5.34 48.7
  • Example 3 50% A-2 + 50% B-70 5.78 50.1
  • Example 4 50% A-2 + 50% B-134 5.34 46.2
  • Example 5 50% A-2 + 50% B-21 4.13 60.4
  • Example 6 50% A-2 + 50% B-23 3.89 62.3
  • Example 7 50% A-2 + 50% B-31 4.34 58.4
  • Example 8 50% A-2 + 50% B-35 4.45 53.2
  • Example 9 50% A-3 + 50% B-1 5.45 46.7
  • Example 10 50% A-3 + 50% B-3 5.57 53.6
  • Example 11 50% A-3 + 50% B-70 5.29 49.9
  • Example 12 50% A-3 + 50% B-134 5.23 47.2
  • Example 13 50% A-3 + 50% B-21 4.02 58.8
  • Example 14 50% A-3 + 50% B-23 3.86 61.2
  • Example 15 50% A-3 + 50% B-31 4.24 59.4
  • Example 16 50% A-3 + 50% B-35 4.
  • Example 40 50% A-12 + 50% B-35 4.99 53.6
  • Example 41 50% A-16 + 50% B-1 5.10 46.9
  • Example 42 50% A-16 + 50% B-3 5.44 49.2
  • Example 43 50% A-16 + 50% B-70 5.56 53.1
  • Example 44 50% A-16 + 50% B-134 5.14
  • Example 45 50% A-16 + 50% B-21 4.01 61.2
  • Example 46 50% A-16 + 50% B-23 3.77 63.2
  • Example 47 50% A-16 + 50% B-31 4.08 59.6
  • Example 48 50% A-16 + 50% B-35 4.23 58.1
  • Example 49 50% A-30 + 50% B-1 5.03 44.6
  • Example 50 50% A-30 + 50% B-3 5.23 50.8
  • Example 51 50% A-30 + 50% B-70 5.35 55.7
  • Example 52 50% A-30 + 50% B-134 5.05 51.6
  • Example 53 50% A-30 + 50% B-21 3.94 60.7
  • Example 54 50% A-30 + 50% B-23 3.68 62.7
  • Example 55 50% A-30 + 50% B-31 4.01 58.9

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Abstract

La présente invention concerne un dispositif électroluminescent organique comprenant une électrode positive, une électrode négative, et une ou plusieurs couches organiques intercalées entre l'électrode positive et l'électrode négative, au moins une des couches organiques comprenant un premier hôte et un second hôte.
PCT/KR2016/000040 2015-01-08 2016-01-05 Élément électroluminescent organique WO2016111515A1 (fr)

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KR10-2015-0002812 2015-01-08
KR1020150002812A KR102360221B1 (ko) 2015-01-08 2015-01-08 유기 전계 발광 소자

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3798210A1 (fr) * 2014-12-24 2021-03-31 Solus Advanced Materials Co., Ltd. Élément électroluminescent organique
EP4198103A1 (fr) 2021-12-14 2023-06-21 Novaled GmbH Diode électroluminescente organique et dispositif le comprenant
EP4199125A1 (fr) 2021-12-14 2023-06-21 Novaled GmbH Diode électroluminescente organique, son procédé de préparation et dispositif la comprenant

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KR20190070586A (ko) 2017-12-13 2019-06-21 엘지디스플레이 주식회사 전자수송 재료용 화합물 및 이를 포함하는 유기 발광 다이오드
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EP4198103A1 (fr) 2021-12-14 2023-06-21 Novaled GmbH Diode électroluminescente organique et dispositif le comprenant
EP4199125A1 (fr) 2021-12-14 2023-06-21 Novaled GmbH Diode électroluminescente organique, son procédé de préparation et dispositif la comprenant
WO2023110608A1 (fr) 2021-12-14 2023-06-22 Novaled Gmbh Diode électroluminescente organique et dispositif la comprenant
WO2023110610A1 (fr) 2021-12-14 2023-06-22 Novaled Gmbh Diode électroluminescente organique, son procédé de préparation et dispositif la comprenant

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