WO2017105039A1 - Nouveau composé et dispositif électroluminescent organique contenant ce composé - Google Patents

Nouveau composé et dispositif électroluminescent organique contenant ce composé Download PDF

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WO2017105039A1
WO2017105039A1 PCT/KR2016/014449 KR2016014449W WO2017105039A1 WO 2017105039 A1 WO2017105039 A1 WO 2017105039A1 KR 2016014449 W KR2016014449 W KR 2016014449W WO 2017105039 A1 WO2017105039 A1 WO 2017105039A1
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group
compound
light emitting
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WO2017105039A9 (fr
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박민수
김근태
안자은
안현철
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주식회사 동진쎄미켐
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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
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene

Definitions

  • the present application relates to a novel compound and an organic light emitting device comprising the compound as an electron transporting layer or a hole blocking layer.
  • an organic light emitting device capable of low-voltage driving with a self-luminous type has a superior viewing angle, contrast ratio, and the like, and is lighter and thinner than a liquid crystal display (LCD), which is a mainstream of flat panel display devices.
  • LCD liquid crystal display
  • the material used as the organic material layer in the organic light emitting device may be largely 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 a function.
  • the light emitting material may be classified into a polymer and a single molecule according to molecular weight, and a fluorescent material derived from a singlet excited state of electrons, a phosphorescent material derived from a triplet excited state of electrons, and a triplet of electrons according to a light emitting mechanism. It can be classified as a delayed fluorescent material resulting from the movement of electrons from a single excited state to a singlet excited state.
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors, depending on the color of light emitted.
  • a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer. The principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to give high efficiency light. At this time, since the wavelength of the host is shifted to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant and the host to be used.
  • Korean Patent Laid-Open Publication No. 2013-0060953 discloses an anthracene derivative-based organic electroluminescent device.
  • the present application is to provide a novel compound and an organic light emitting device comprising the compound as an electron transport layer or a hole blocking layer.
  • a first aspect of the present application provides a compound represented by the following Chemical Formula 1:
  • R 1 and R 2 are each independently hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C 6 to C 50 aryl, or substituted or unsubstituted C 2 to C 50 is a hetero aryl group
  • X is substituted or unsubstituted CR 3 or N
  • R 3 is hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C 6 to C 50 aryl, or Substituted or unsubstituted C 2 to C 50 hetero aryl group
  • L is substituted or unsubstituted C 6 to C 30 arylene or C 3 to C 20 hetero arylene group
  • Z is N or CR 3
  • R 1 may form a ring with ⁇ carbon of the surrounding aryl ( ⁇ carbon of the repeating unit m or ⁇ carbon of R 2 )
  • m and n are each independently an integer of 0 to 2, provided that
  • the second aspect of the present application provides an organic light emitting device comprising at least one organic layer containing a compound according to the first aspect of the present application formed between the anode electrode and the cathode electrode.
  • the phosphine oxide unit included in the compound has a strong electron attracting effect and low HOMO (highest occupied molecular orbital) compared to the conventional heterocyclic compound Since it has a level, the electron transporting property and hole blocking property become strong, thereby achieving low voltage high efficiency and high color purity of the organic light emitting element.
  • the phosphine oxide unit prevents the increase in the conjugated bond length, it is possible to maintain high singlet energy and triplet energy.
  • the X and Y axis coordinates of the CIE color coordinates can be reduced.
  • FIG. 1 schematically illustrates a cross section of an organic light emitting device according to an embodiment of the present disclosure.
  • FIG. 2 is a graph illustrating current density characteristics of an organic light emitting diode according to an exemplary embodiment of the present disclosure.
  • FIG. 3 is a graph illustrating current efficiency characteristics of an organic light emitting diode according to an exemplary embodiment of the present disclosure.
  • FIG. 4 illustrates an electroluminescence spectrum of an organic light emitting diode according to an exemplary embodiment of the present disclosure.
  • FIG. 5 is a graph illustrating the lifespan of the organic light emitting diode according to the exemplary embodiment of the present application.
  • FIG. 6 is a graph illustrating current density characteristics of an organic light emitting diode according to an exemplary embodiment of the present disclosure.
  • FIG. 7 is a graph illustrating current efficiency characteristics of an organic light emitting diode according to an exemplary embodiment of the present disclosure.
  • FIG. 8 illustrates an electroluminescence spectrum of an organic light emitting diode according to an exemplary embodiment of the present disclosure.
  • FIG 9 is a graph illustrating the lifespan of the organic light emitting diode according to the exemplary embodiment of the present application.
  • the term "combination (s) thereof" included in the expression of a makushi form refers to one or more mixtures or combinations selected from the group consisting of components described in the expression of makushi form, It means to include one or more selected from the group consisting of the above components.
  • aromatic ring or “aryl” means to include at least one aromatic hydrocarbon group
  • aromatic hetero ring or “hetero aryl” means at least one aromatic hydrocarbon group and at least one hetero atom. As it means to include, it represents that at least one carbon atom of the aromatic hydrocarbon group is substituted by a hetero atom.
  • aromatic ring (aryl) or aromatic hetero ring (hetero aryl) includes a plurality of rings
  • the aromatic ring or the aromatic hetero ring includes one aromatic ring and as an additional ring, an aromatic ring or a non-aromatic ring It may be to include.
  • the plural ring may include at least one aromatic ring and an additional ring bonded to one atom or fused through two or more atoms, but may not be limited thereto.
  • the aryl is, for example, a benzene ring, toluene ring, naphthalene ring, anthracene ring, phenanthrene ring, pentarene ring, indene ring, biphenylene ring, phenylene ring, azene ring, heptarene ring, acenaph Tylene ring, fluorene ring, tetracene ring, triphenylene ring, pyrene ring, chrysene ring, ethyl-crysene ring, pysene ring, perylene ring, pentaphene ring, pentacene ring, tetraphenylene ring, hexa Pen ring, he
  • the heteroaryl may be, for example, 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, 1-indolyl group, 2-indole Reel group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindoleyl group, 2-isoindoleyl group, 3-isoindoleyl group, 4- Isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4- Benzofuranyl group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl
  • hetero atom means an atom other than carbon and hydrogen atoms, for example, the hetero atom is Si, Se, N, O, S, P, As, F, Cl, Br And I, but may include those selected from the group consisting of, but may not be limited thereto.
  • halogen or “halo” means that a halogen atom belonging to group 17 of the periodic table is included in the compound in the form of a functional group, and may be, for example, chlorine, bromine, fluorine or iodine. However, this may not be limited.
  • substituted or unsubstituted is CN, hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C 6 to C 50 aryl group, or substituted or unsubstituted C 2 It may include a substituent such as C 50 hetero aryl group.
  • a first aspect of the present application provides a compound represented by the following Chemical Formula 1:
  • R 1 to R 2 are each independently hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C 6 to C 50 aryl, or substituted or unsubstituted C 2 to C 50 is a hetero aryl group
  • X is substituted or unsubstituted CR 3 or N
  • R 3 is hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C 6 to C 50 aryl, or Substituted or unsubstituted C 2 to C 50 hetero aryl group
  • L is substituted or unsubstituted C 6 to C 30 arylene or C 3 to C 20 hetero arylene group
  • Z is N or CR 3
  • R 1 may form a ring with ⁇ carbon of surrounding aryl
  • m and n are each independently an integer of 0 to 2, provided that when X is CR 3 , n is not 0. In this case, the ⁇
  • R 1 when R 1 forms a ring with ⁇ carbon of the surrounding aryl, it may have high thermal stability by increasing the rigidity of the molecule.
  • the electron transport increasing (LUMO) energy level is lowered by using the compound represented by Chemical Formula 1 as an electron transporting material, a large amount of electrons are injected into the light emitting layer because electrons are facilitated. The efficiency of the organic light emitting device can be increased.
  • LUMO electron transport increasing
  • by using the compound represented by the formula (1) as a hole blocking layer to prevent holes from leaking to the electron transport layer and the hole remains in the light emitting layer may increase the efficiency of the organic light emitting device.
  • each of R 1 to R 3 may include one selected independently from the following substituents, but may not be limited thereto:
  • Y is each independently, C, N, or CR 4
  • R 4 is hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C 6 to C 50 aryl group or substituted or unsubstituted C 2 to C 50 heteroaryl group.
  • L may be selected from the following substituents, but may not be limited thereto:
  • Y is each independently, C, N, or CR 4
  • R 4 is hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C 6 to C 50 aryl group or substituted or unsubstituted C 2 to C 50 heteroaryl group.
  • the compound may include, but is not limited to, one represented by one of the following formulas:
  • the compound may be prepared by a method for preparing a compound represented by Scheme 1, but may not be limited thereto.
  • R 1 to R 2 are each independently hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C 6 to C 50 aryl, or substituted or unsubstituted C 2 to C 50 is a hetero aryl group
  • X is substituted or unsubstituted CR 3 or N
  • R 3 is hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C 6 to C 50 aryl, or Substituted or unsubstituted C 2 to C 50 hetero aryl group
  • L is substituted or unsubstituted C 6 to C 30 arylene or C 3 to C 20 hetero arylene group
  • Z is N or CR 3
  • R 1 may form a ring with ⁇ carbon of surrounding aryl
  • m and n are each independently an integer of 0 to 2, provided that when X is CR 3 , n is not 0. In this case, the ⁇
  • R 1 when R 1 forms a ring with ⁇ carbon of the surrounding aryl, it may have high thermal stability by increasing the rigidity of the molecule.
  • each of R 1 to R 3 may include one selected independently from the following substituents, but may not be limited thereto:
  • Y is each independently, C, N, or CR 4
  • R 4 is hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C 6 to C 50 aryl group or substituted or unsubstituted C 2 to C 50 heteroaryl group.
  • L may be selected from the following substituents, but may not be limited thereto:
  • Y is each independently, C, N, or CR 4
  • R 4 is hydrogen, deuterium, halogen, nitro group, nitrile group, substituted or unsubstituted C 6 to C 50 aryl group or substituted or unsubstituted C 2 to C 50 heteroaryl group.
  • the second aspect of the present application provides an organic light emitting device comprising at least one organic layer containing a compound according to the first aspect of the present application formed between the anode electrode and the cathode electrode.
  • the organic light emitting device may include one or more organic material layers including the compound represented by the formula (1).
  • the organic material layer including the compound represented by Formula 1 may be an electron transport layer or a hole blocking layer.
  • the compound may be used alone or in combination with a known electron injecting material or a compound for an electron transporting material as the electron transporting material, but may not be limited thereto.
  • the organic light emitting device is a hole injection layer (HIL), hole transport layer (HTL), light emitting layer (EML), electron transport layer (ETL), electron injection between the anode (anode) and the cathode (cathode)
  • HIL hole injection layer
  • HTL hole transport layer
  • EML light emitting layer
  • ETL electron transport layer
  • EIL electron injection between the anode (anode) and the cathode (cathode)
  • EIL organic material layer
  • EIL electron transport layer
  • Figure 1 schematically shows a cross-section of an organic light emitting device according to an embodiment of the present application.
  • an organic light emitting diode includes an anode electrode 11 formed on a substrate 10, a hole injection layer 12 formed on the anode electrode 11, and the hole injection layer.
  • a hole transport layer 13 formed on the hole 12 a light emitting layer 14 formed on the hole transport layer 13, an electron transport layer 15 formed on the light emitting layer 14, and electrons formed on the electron transport layer 15. It may include an injection layer 16 and a cathode electrode 17 formed on the electron injection layer 16, but may not be limited thereto.
  • the organic light emitting device according to the embodiment of the present application may be manufactured by the following method.
  • an anode electrode 11 is formed by depositing an anode electrode material having a low work function on the substrate 10 to enable injection of holes.
  • the substrate 10 may be used without particular limitation as long as it is a substrate used in a conventional organic light emitting device, in particular mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproof It may be to include an excellent glass substrate or a transparent plastic substrate, but may not be limited thereto.
  • the anode electrode 11 is transparent and has excellent conductivity indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), and their It may be to include one selected from the group consisting of combinations, but may not be limited thereto.
  • the anode electrode material may be deposited by a conventional anode electrode forming method, for example, may be deposited on a substrate by a deposition method or a spattering method, but may not be limited thereto.
  • the hole injection layer 12 may be formed on the anode 11 by vacuum deposition, spin coating, casting, or Langmuir-Bloodjet (LB), but is not limited thereto. Can be.
  • the hole injection layer 12 may be formed by a vacuum deposition method which is easy to obtain a uniform film quality and is hard to generate pin holes.
  • the compound used as a material of the hole injection layer 12 or the structure and thermal characteristics of the hole injection layer 12 of interest Depending on the deposition conditions, but generally a deposition temperature of about 50 ° C.
  • the hole injection layer 12 material may be used without particular limitation, TCTA [4, which is a phthalocyanine compound or starburst type amine derivatives such as copper phthalocyanine disclosed in US Patent No. 4,356,429 4 ', 4 "-tri (N-carbazolyl) triphenylamine], m-MTDATA [4,4', 4" -tris (3-methylphenylamino) triphenylamine], m-MTDAPB [4,4 ' , 4 "-tris (3-methylphenylamino) phenoxybenzene], or HI-406 [N 1 , N 1 '-(biphenyl-4,4'-diyl) bis (N 1-(naphthalen- 1 -yl ) -N 4 , N 4 -diphenylbenzene-1,4-diamine] may be used as the hole injection layer material, but may not be limited thereto.
  • TCTA is a phthalocyanine compound or starburs
  • the hole transport layer 13 may be formed on the hole injection layer 12 by a method such as vacuum deposition, spin coating, casting, or LB, but may not be limited thereto.
  • the hole transport layer 13 may be formed by a vacuum deposition method which is easy to obtain a uniform film quality and is hard to generate pin holes.
  • the deposition conditions vary depending on the compound used, but in general, the hole transport layer 13 is preferably selected in a condition range substantially the same as the deposition conditions of the hole injection layer. .
  • the material of the hole transport layer 13 may be used without particular limitation, and may be arbitrarily selected from conventionally known materials used as the hole transport layer 13.
  • the hole transport layer 13 material is a carbazole derivative such as N-phenylcarbazole, polyvinylcarbazole, N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1, Aromatic condensed rings such as 1-biphenyl] -4,4'-diamine (TPD) or N.N'-di (naphthalen-1-yl) -N, N'-diphenyl benzidine ( ⁇ -NPD) Eggplant can be used a conventional amine derivative and the like.
  • the light emitting layer 14 may be formed on the hole transport layer 13 by a method such as vacuum deposition, spin coating, casting, LB, or the like, but may not be limited thereto.
  • the light emitting layer 14 may be formed by a vacuum deposition method which is easy to obtain a uniform film quality and is hard to generate pin holes.
  • the deposition conditions are different depending on the compound to be used, but in general, it is preferable to select in a condition range almost the same as the deposition conditions of the hole injection layer.
  • the light emitting layer 14 may be a known host or dopant.
  • the fluorescent dopant may be IDE102 or IDE105 available from Idemitsu, or BD142 (N 6 , N 12 -bis (3,4-dimethylphenyl) -N 6 , N 12 -dimethyryl).
  • Sen-6,12-diamine may be a green phosphorescent dopant ⁇ Ir (ppy) 3 [tris (2-phenylpyridine) iridium] ⁇ , a blue phosphorescent dopant F 2 Irpic ⁇ iridium (III) Bis [4,6-difluorophenyl) -pyridinato-N, C2 '] picolinate) ⁇ , a red phosphorescent dopant RD61 from UDC, and the like can be co-vacuum deposited (doped).
  • the doping concentration of the dopant is not particularly limited, but it is preferable that the dopant is about 0.01 to about 15 parts by weight based on 100 parts by weight of the host.
  • a hole suppressing material (HBL) is further laminated by vacuum deposition or spin coating. It is preferable.
  • the hole-suppressing material which can be used at this time is not specifically limited, Any thing can be selected and used from the well-known thing used as a hole-suppressing material.
  • the hole suppressing material may include an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, or a hole suppressing material described in Japanese Patent Laid-Open No. 11-329734 (A1).
  • Bis (8-hydroxy-2-methylquinolinolato) -aluminum biphenoxide], or a phenanthrolines-based compound e.g., UDC Corporation BCP (Basocuproin)
  • UDC Corporation BCP Basocuproin
  • the electron transport layer 15 is formed on the light emitting layer 14.
  • the electron transport layer 15 may be formed by a method such as vacuum deposition, spin coating, casting, or LB, but may not be limited thereto. Preferably, the electron transport layer 15 may be formed.
  • the deposition conditions vary depending on the compound used, but in general, the electron transport layer 15 is preferably selected in a condition range substantially the same as the deposition conditions of the hole injection layer. .
  • the electron transport layer 15 functions to stably transport electrons injected from an electron injection electrode (cathode electrode 17), and the compound represented by Chemical Formula 1 is used alone. Or known mixtures of electron transport layers may be used.
  • the electron transport properties are enhanced by the phosphine oxide unit included in the compound, accordingly the organic light emitting device Low voltage and high efficiency characteristics can be achieved.
  • the recombination region is moved by the phosphine oxide unit, so that color coordinates x and y may be reduced.
  • the phosphine oxide unit prevents the increase in the conjugated bond length, it is possible to maintain a high triplet energy.
  • the electron injection layer (EIL) 16 that is a material having a function of facilitating the injection of electrons from the cathode (cathode electrode 17) on the electron transport layer 15 is laminated It may further include, but may not be limited to this.
  • the electron injection layer 16 may be a material selected from the group consisting of LiF, NaCl, CsF, Li 2 O, BaO, and combinations thereof, but may not be limited thereto. .
  • a compound represented by Chemical Formula 1 may be further included as the hole blocking layer between the emission layer 14 and the electron transport layer 15, but is not limited thereto. Can be.
  • the compound represented by Formula 1 as a hole blocking layer, holes may be prevented from leaking to the electron transport layer, and the holes may remain in the light emitting layer to increase the efficiency of the organic light emitting device.
  • the cathode forming metal can be formed on the electron injection layer 16 by vacuum deposition or sputtering and used as the cathode electrode 17.
  • the cathode electrode 17 may include one selected from the group consisting of lithium, magnesium, aluminum, calcium, indium, silver, gold, and combinations thereof, but may not be limited thereto.
  • a transmissive cathode using ITO, IZO, SnO 2 , or ZnO may be used as the cathode electrode 17 to obtain a front light emitting device, but may not be limited thereto.
  • the organic light emitting device is not only an anode, a hole injection layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injection layer, and a cathode structure, but also an organic light emitting device having a variety of structures, 1 It is also possible to form additional layers or intermediate layers of two layers.
  • each organic material layer formed in accordance with one embodiment of the present application can be adjusted according to the required degree, preferably may include about 10 nm to about 1,000 nm, more preferably about 20 nm to about 150 It may be one containing nm.
  • the organic material layer including the compound represented by the formula (1) has the advantage that the surface is uniform, excellent in shape stability because the thickness of the organic material layer can be adjusted in molecular units.
  • Reactant 1 was used instead of Reactant 5 to synthesize the following compounds:
  • Reactant 2 was used instead of Reactant 5 to synthesize the following compounds:
  • Reactant 1 was used instead of Reactant 2 to synthesize the following compounds:
  • the following reactants 1 to 5 were used as reactants for preparing the organic light emitting device.
  • Compound 3 was synthesized using the same method as compound 1, but using reactant 2 instead of reactant 1.
  • Compound 4 was synthesized using the same method as compound 1, but using reactant 2 instead of reactant 1, and using intermediate 2 instead of intermediate 1.
  • Compound 6 was synthesized using the same method as compound 1, but using reactant 3 instead of reactant 1.
  • Compound 7 was synthesized using the same method as compound 1, but using reactant 4 instead of reactant 1, and using intermediate 2 instead of intermediate 1.
  • Compound 8 was synthesized using the same method as compound 1, but using reactant 4 instead of reactant 1.
  • an organic light emitting device according to the present embodiment was manufactured.
  • the organic light emitting device is composed of an anode electrode (hole injection electrode 11) / hole injection layer 12 / hole transport layer 13 / light emitting layer 14 / electron transport layer 15 / cathode electrode [electron injection electrode 17)] in order.
  • the following materials were used as the hole injection layer 12, the hole transport layer 13, the light emitting layer 14, and the electron transport layer 15 of this example and the comparative example:
  • the glass substrate coated with the indium tin oxide (ITO) thin film having a thickness of 1500 ⁇ was washed with distilled water ultrasonically. After the distilled water was washed, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, or methanol was dried and dried. The substrate was then transferred to a plasma scrubber and then the substrate was cleaned for 5 minutes using an oxygen plasma. Subsequently, HT01 600 kV as a hole injection layer and Ref. 4 and 250 kV as a hole transport layer were formed into a film using a thermal evaporator on the ITO substrate.
  • ITO indium tin oxide
  • BH01: BD01 was doped at 5% as a light emitting layer to form a film having a thickness of 250 kHz.
  • the prepared compound 1 and Liq were formed into a film having a thickness of 300 ⁇ s at a 1: 1 ratio, and then LiF 10 ⁇ s and aluminum (Al) 1,000 ⁇ s were formed and the device was encapsulated in a glove box.
  • An organic light emitting device was manufactured by
  • An organic light emitting device was manufactured in the same manner as in Example 1, where an organic light emitting device in which an electron transporting layer was formed using the prepared compounds 2 to 18, respectively.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, but using ET-01 instead of Compound 1 as an electron transporting layer.
  • the organic light emitting device according to the present embodiment was confirmed that the physical properties compared to the comparative example.
  • 2 to 5 are graphs showing current density characteristics, current efficiency characteristics, electroluminescence spectra, and lifetime of the organic light emitting diode according to Example 6, respectively.
  • 6 to 9 are graphs showing current density characteristics, current efficiency characteristics, electroluminescence spectra, and lifetime of the organic light emitting diode according to Example 8, respectively.

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Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique comprenant ledit composé en tant que couche de transport d'électrons ou que une couche de blocage de trous.
PCT/KR2016/014449 2015-12-14 2016-12-09 Nouveau composé et dispositif électroluminescent organique contenant ce composé WO2017105039A1 (fr)

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CN201680073475.0A CN108368065A (zh) 2015-12-14 2016-12-09 新颖化合物及包含其的有机发光器件

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KR1020150178423A KR20170070640A (ko) 2015-12-14 2015-12-14 신규한 화합물 및 이를 포함하는 유기 발광 소자
KR10-2015-0178423 2015-12-14

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