WO2018221985A1 - Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant - Google Patents

Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant Download PDF

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WO2018221985A1
WO2018221985A1 PCT/KR2018/006240 KR2018006240W WO2018221985A1 WO 2018221985 A1 WO2018221985 A1 WO 2018221985A1 KR 2018006240 W KR2018006240 W KR 2018006240W WO 2018221985 A1 WO2018221985 A1 WO 2018221985A1
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group
compound
light emitting
layer
substituted
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PCT/KR2018/006240
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English (en)
Korean (ko)
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양정훈
이동훈
허정오
장분재
허동욱
한미연
정민우
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주식회사 엘지화학
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Priority claimed from KR1020180062154A external-priority patent/KR102064993B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880027499.1A priority Critical patent/CN110573498B/zh
Priority to US16/609,199 priority patent/US11453650B2/en
Publication of WO2018221985A1 publication Critical patent/WO2018221985A1/fr

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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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D251/14—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 with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—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 with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • 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

Definitions

  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent in brightness, driving voltage and response speed characteristics, many studies have been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode.
  • the organic layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel heterocyclic compound compound and an organic light emitting device comprising the same.
  • the present invention provides a binaphthalene compound represented by the following Chemical Formula 1.
  • 1 ⁇ is a single bond or a substituted or unsubstituted C 0 aryl
  • L 2 is a single bond, substituted or unsubstituted C 6 60 aryl, or substituted or unsubstituted C 5-60 heteroaryl,
  • Ai is represented by the following Chemical Formula 2, Chemical Formula 3, Chemical Formula 4, or Chemical Formula 5,
  • X L5 X 2 , and X 3 are each independently N or CR 4 , wherein N is at least one,
  • X 5 are each independently N or CR 5 , wherein N is at least one
  • R u R 2 , and R 3 are each independently substituted or unsubstituted d_ 40 alkyl, substituted or unsubstituted C 0 aryl, or substituted or unsubstituted C 5 60 heteroaryl, or R,, R 2 , And R 3 are each independently hydrogen of the alkyl, aryl, heteroaryl substituted with deuterium or CN,
  • R 4, and R 5 are each independently hydrogen, deuterium, substituted or unsubstituted CMO alkyl, substituted or unsubstituted C 6 _ 60 aryl, or substituted or unsubstituted C 5 heteroaryl.
  • the present invention is a first electrode;
  • An organic light emitting device including a second electrode provided to face the first electrode and one or more organic material layers provided between the first electrode and the second electrode, wherein one sub-layer of the organic material layer is represented by Chemical Formula 1.
  • an organic light emitting device comprising the compound represented.
  • the compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
  • it represented by the above formula (I) compounds may 'be used as a hole injection, hole transport, hole injection and transport, emission, electron transportation, or the electron injecting material.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
  • FIG. 2 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • * —— and ⁇ refer to a bond connected to another substituent.
  • substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the ester group may be substituted with oxygen of the ester group having 1 to 25 carbon atoms, a linear, branched or cyclic alkyl group or an aryl group having 6 to 25 carbon atoms.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • the carbon number of the imide group is not particularly limited : It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, and phenylboron group.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, nuclear chamber, n-nuclear chamber, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, Heptyl, n-heptyl, 1-methylnucleus, cyclopentylmethyl, cyclonuxylmethyl, octyl, ⁇ ⁇ Octyl, tert-octyl, 1-methylheptyl, 2-ethylnuclear, 2-propyl
  • the alkenyl number may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • aryl group is not particularly limited, but may include 6 to 6 carbon atoms.
  • the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • polycyclic aryl group examples include naphthyl group, anthracenyl group, phenanthryl group, It may be a pyrenyl group, a perrylenyl group, a chrysenyl group, a fluorenyl group and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. Substituted fluorenyl groups
  • the heterocyclic group is a heterocyclic group containing one or more of O, N, Si, and S as heterologous elements, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic group examples include a thiophene group, a furan group, a fluorine group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group, and an acri Dill group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole Group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group,
  • the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above.
  • the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group of the aralkenyl group It is the same as the example of the alkenyl group mentioned above.
  • the description of the aryl group described above may be applied except that the arylene is a divalent group.
  • the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding.
  • the heterocyclic group is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding.
  • Chemical Formula 1 according to a structure in which a specific cyano group is bonded to Ar with a binaphthalene group bonded thereto, Chemical Formula 1 is represented by Chemical Formulas 1-1, 1-2, 1-3, 1-4, 1 It may be represented as -5, 1-6, or 1-7:
  • L l3 L 2, R l3 R 2, and R 3 are described as eu
  • L 2 defined in formula (I) is a single bond, phenylene group (phenylene), or by phenylene groups (biphenylene) each independently .
  • 3 ⁇ 4, 3 ⁇ 4, and X 5 are each independently N.
  • R b R 2 , R 3 , R 4, and R 5 are each independently hydrogen, a phenyl group, or a pyridinyl group.
  • Ar ⁇ l of the compound represented by Chemical Formula 1 is represented by Chemical Formula 2, wherein: ⁇ is phenylene, and L 2 is a single bond compound may be prepared by the same method as in Scheme 1 below.
  • the remaining compounds in the compound of Formula 1 may also be prepared by the same or similar method as that of Banung Formula 1 by applying a counterungmul having different substituents.
  • the manufacturing method may be more specific in the production examples to be described later.
  • the present invention also provides an organic light emitting device including the compound represented by Chemical Formula 1.
  • the present invention comprises a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. do.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer as an organic layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic layer may include a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes, and the hole injecting layer, a hole transporter, or a layer for simultaneously injecting and transporting a hole may be represented by Formula 1 above. It includes a compound represented.
  • the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the organic layer may include an electron transport layer, or an electron injection layer, the electron transport layer, or the electron injection layer comprises a compound represented by the formula (1).
  • the electron transport layer, the electron injection layer, or the layer for the electron transport and the electron injection at the same time includes a compound represented by the formula (1).
  • the organic material layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by Chemical Formula 1.
  • the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • the structure of the organic light emitting device according to this is illustrated in FIGS. 1 and 2.
  • 1 shows an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 An example of the device is shown.
  • the compound represented by Formula 1 may be included in the light emitting layer.
  • the compound represented by Formula 1 may be included in one or more layers of the hole injection worm, hole transport layer, light emitting layer and electron transport layer.
  • the organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
  • PVD physical vapor deposition
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then, a material that may be used as a cathode may be deposited thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode ' material on a substrate (WO 2003/012890). However, the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode.
  • the anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material include metals such as vanadium, crumb, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide ( ⁇ ), indium zinc oxide (IZO); A combination of a metal and an oxide such as ⁇ : ⁇ 1 or SN0 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto. no. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, kale, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from an electrode, and has a capability of transporting holes with a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect with respect to a light emitting layer or a light emitting material, and is produced in the light emitting layer.
  • the compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • the hole injecting material is a metal porphyrin (porphyrin), oligothiophene, arylamine series of organic matter, hex nitrile hex-aza triphenyl "organic Len based organic material, quinacridone (quinacridone) series of perylene (perylene) Organic matter Anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • the hole transport layer is a material that can transport holes from an anode or a hole injection layer to a light emitting layer. This is suitable.
  • the light emitting material includes holes and electrons from the hole transport layer and the electron transport layer.
  • a material capable of emitting light in the visible light region by transporting and binding each of them a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, and periplanthene having an arylamino group.
  • the styrylamine compound is a compound in which at least one arylvinyl group is substituted with substituted or unsubstituted arylamine, and a substituent selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group Is substituted or unsubstituted.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material that can inject electrons well from the cathode and transfer them to the light emitting layer. Suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transporting layer is a conventional material according to any of the examples of "may be used.
  • suitable cathode material with the desired cathode material after the aluminum layer or silver layer has a low work function, as used according to the prior art. More specifically, Cesium, barium, calcium, ytterbium and samarium, each followed by an aluminum layer or a silver layer, the electron injection layer being a layer for injecting electrons from the electrode, having the ability to transport electrons, the effect of electron injection from the cathode, A compound having an excellent electron injection effect on the light emitting layer or the light emitting material, preventing migration of excitons generated in the light emitting layer to the hole injection layer, and excellent in thin film formation ability is preferable.
  • the organic light emitting device may be a top emission type, a bottom emission type or a double-sided emission type according to the material used.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device. The production of the compound represented by Chemical Formula 1 and the organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
  • a glass substrate coated with a thickness of 1,000 A of ITO (indium tin oxide) was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • the ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, methanol After drying it was transported to a plasma scrubber.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the following compound [HI-A] was vacuum-deposited to a thickness of 600 A on the ⁇ transparent electrode thus prepared to form a hole injection layer.
  • the following compound [HAT] (50 A) and the following compound [HT-A] (600 A) were sequentially vacuum deposited on the hole injection layer to form a hole transport layer.
  • the following Compounds [BH] and [BD] were vacuum-deposited at a weight ratio of 25: 1 on the hole transport layer to have a film thickness of 200 A to form a light emitting layer.
  • Compound 1 prepared in Preparation Example 1 and the following compound [LiQ] (Lithiumquinolate) were vacuum-deposited at a weight ratio of 1: 1 on the emission layer to form an electron injection and transport layer at a thickness of 350 A.
  • Lithium fluoride (LiF) and aluminum at 1,000 A thickness were sequentially deposited on the electron injection and transport layer to form a cathode.
  • An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using one compound of Compounds 2 to 11 as described in Table 1 instead of Compound 1 in Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using Compound (IV) having the following structure as described in Table 1 instead of Compound 1 in Example 1-1.
  • the driving voltage and the luminous efficiency of the organic light emitting diodes manufactured in Examples 1-1 to 1-11 and Comparative Examples 1-1 to 1-4 were measured at a current density of 10 mA / cm 2 , and 20 mA.
  • the time (T 90 ) of 90% of the initial luminance at a current density of / cm 2 was measured. The results are shown in Table 1 below.
  • the heterocyclic compound represented by the formula (1) having an asymmetric structure based on the binaphthalene skeleton bonded to each cyan group and hetero ring according to the present invention is electron injection and electron of the organic light emitting device It can be seen that it can be used for the organic material layer that can simultaneously transport.
  • a compound in which a binaphthalene skeleton structure is asymmetrically bonded to a hetero ring such as triazine as in Chemical Formula 1
  • heterocyclic compound represented by Formula 1 has better thermal stability than a material having a high molecular weight, such as compound (I) having a symmetrical structure, as in Comparative Example 1-1, and a deep HOMO level of 6.0 eV or more. This is because it has high triplet energy (ET) and hole stability.
  • Example 1-1 and Comparative Example 1-3 are compared, even in the case of a hetero compound including binaphthalene, when naphthyl and biphenylene are combined with the compound (III) when used in an organic light emitting device It showed superior characteristics in terms of driving voltage, efficiency and lifespan over materials having a structure of the structure. Also, when Examples 1-1 to 1-11 and Comparative Example 1-4 were compared, biscuits were obtained as in Compound (IV). Electron transport capacity, band gap, energy level and thermal characteristics when the two functional groups bonded to the binaphthalene skeleton have different structures compared to the case where the two functional groups bonded to the naphthalene skeleton are both triazine-based structures.
  • heterocyclic compound represented by Chemical Formula 1 when used in an organic material layer capable of simultaneous electron injection and electron transport, n-type dopants used in the art may be mixed and used. Accordingly, the heterocyclic compound represented by Formula 1 has a low driving voltage and high efficiency, and may improve stability of the device by hole stability of the compound.
  • a glass substrate coated with a thickness of 1,000 A of ITO (indium tin oxide) was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the following compound [HI-A] was thermally vacuum deposited to a thickness of 600 A on the prepared ITO transparent electrode to form a hole injection layer.
  • the following compound [HAT] (50 A) and the following compound [HT-A] (600 A) were sequentially vacuum deposited on the hole injection layer to form a hole transport layer.
  • the following Compounds [BH] and [BD] were vacuum-deposited at a weight ratio of 25: 1 on the hole transport layer to have a film thickness of 200 A to form a light emitting layer.
  • Compound 1 prepared in Preparation Example 1 was vacuum-deposited on the emission layer to form an electron control layer with a thickness of 200 A.
  • the following compound [ET] and the following compound [LiQ] (Lithiumquinolate) were vacuum-deposited at a weight ratio of 1: 1 on the electron control layer to form an electron injection and transport layer at a thickness of 150 A.
  • Lithium fluoride (LiF) and aluminum at 1,000 A thickness were sequentially deposited on the electron injection and transport layer to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 to 9 A / sec
  • the lithium fluoride of the cathode was maintained at 0.3 A / sec
  • the aluminum was maintained at the deposition rate of 2 A / sec.
  • An organic light emitting device was manufactured by maintaining 7 to 5xl (r 8 torr).
  • An organic light-emitting device was manufactured in the same manner as in Example 2-1, except for using one compound of Compounds 2 to 11 as described in Table 2 instead of Compound 1 in Example 2-1.
  • Example 2-1 Except for using the compound (I), (II), or (III) of the structure shown in Table 2 instead of compound 1 in Example 2-1 in the same manner as in Example 2-1 The device was produced.
  • An organic light emitting diode was manufactured according to the same method as Example 2-1 except for using the compound (IV) having the following structure as described in Table 2 instead of the compound 1 in Example 2-1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé hétérocyclique et un élément électroluminescent organique le comprenant.
PCT/KR2018/006240 2017-05-31 2018-05-31 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant WO2018221985A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201880027499.1A CN110573498B (zh) 2017-05-31 2018-05-31 新的杂环化合物和包含其的有机发光器件
US16/609,199 US11453650B2 (en) 2017-05-31 2018-05-31 Heterocyclic compound and organic light emitting device comprising the same

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KR10-2017-0067648 2017-05-31
KR20170067648 2017-05-31
KR10-2018-0062154 2018-05-30
KR1020180062154A KR102064993B1 (ko) 2017-05-31 2018-05-30 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자

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WO2018221985A1 true WO2018221985A1 (fr) 2018-12-06

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120051598A (ko) * 2010-11-12 2012-05-22 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 전자 소자
KR20120061056A (ko) * 2010-11-04 2012-06-12 주식회사 엘지화학 신규한 질소 함유 헤테로환 화합물 및 이를 이용한 유기 전자 소자
KR20150025259A (ko) * 2013-08-28 2015-03-10 삼성디스플레이 주식회사 화합물 및 이를 포함한 유기 발광 소자
KR20150039486A (ko) * 2013-10-02 2015-04-10 삼성디스플레이 주식회사 화합물 및 이를 포함한 유기 발광 소자
WO2017099430A1 (fr) * 2015-12-08 2017-06-15 주식회사 두산 Composé organique et dispositif électroluminescent organique le comprenant

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120061056A (ko) * 2010-11-04 2012-06-12 주식회사 엘지화학 신규한 질소 함유 헤테로환 화합물 및 이를 이용한 유기 전자 소자
KR20120051598A (ko) * 2010-11-12 2012-05-22 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 전자 소자
KR20150025259A (ko) * 2013-08-28 2015-03-10 삼성디스플레이 주식회사 화합물 및 이를 포함한 유기 발광 소자
KR20150039486A (ko) * 2013-10-02 2015-04-10 삼성디스플레이 주식회사 화합물 및 이를 포함한 유기 발광 소자
WO2017099430A1 (fr) * 2015-12-08 2017-06-15 주식회사 두산 Composé organique et dispositif électroluminescent organique le comprenant

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