WO2018221986A1 - Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant - Google Patents

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

Info

Publication number
WO2018221986A1
WO2018221986A1 PCT/KR2018/006241 KR2018006241W WO2018221986A1 WO 2018221986 A1 WO2018221986 A1 WO 2018221986A1 KR 2018006241 W KR2018006241 W KR 2018006241W WO 2018221986 A1 WO2018221986 A1 WO 2018221986A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
light emitting
compound
layer
organic light
Prior art date
Application number
PCT/KR2018/006241
Other languages
English (en)
Korean (ko)
Inventor
양정훈
이동훈
허정오
장분재
허동욱
한미연
정민우
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from KR1020180062155A external-priority patent/KR102064994B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880009529.6A priority Critical patent/CN110248928B/zh
Publication of WO2018221986A1 publication Critical patent/WO2018221986A1/fr

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • 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
    • C07D401/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection 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 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 Korea Patent Publication No. 10- 2000-00 5 to 18 No. 26
  • 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.
  • L 2 is a single bond, substituted or unsubstituted 60 aryl, or substituted or unsubstituted C 5 60 heteroaryl,
  • Ar is represented by the following Chemical Formula 2 or Formula 3,
  • R u and R 2 are hydrogen, deuterium, substituted or unsubstituted C M0 alkyl, substituted or unsubstituted C 6 _ 60 aryl, substituted or unsubstituted C 5-60 heteroaryl, or substituted or unsubstituted c 6 -60 condensed polycyclic group.
  • the present invention is 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 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.
  • the compound represented by Chemical Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emission, electron transport, or electron injection 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 consisting 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.
  • the term "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 or more substituents selected from the group consisting of heterocyclic groups including one or more of N, O and S atoms
  • the 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.
  • Ester group has 1 carbon atoms of ester group
  • carbon number of an imide group is not specifically 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, phenylboron group, and the like.
  • 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-methylnuclear, cyclopentylmethyl , cyclonuxylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylnuclear,
  • the alkenyl group may be linear or branched chain, the 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 preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group.
  • 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 monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, 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. When the fluorenyl group is substituted,
  • the heterocyclic group is a heterocyclic group containing one or more of 0, N, Si, and S as a dissimilar element, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic group examples include thiophene group, furan group, pyr group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group and acri Dill group, pyridazine group, pyrazinyl group, quinolanyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, Pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, Benzofuranyl group, phenanthroline group, iso
  • 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 in the aralkenyl group is the same as the example of the alkenyl group described above.
  • Chemical Formula 1 may be represented by the following Chemical Formula 1-1 or 1-2:
  • R h and R 2 are as defined in the formula (1).
  • L 2 are each independently a single bond or a phenylene group.
  • R! And R 2 are each independently a methyl group, an ethyl group, a phenyl group, a cyanophenyl group, or a pyridinyl group.
  • Ar ⁇ l of the compound represented by Chemical Formula 1 may be represented by Chemical Formula 2, wherein 1 ⁇ is phenylene, and L 2 may be a single bond, which may be prepared by the same method as in Scheme 1 below.
  • Ar ⁇ l may be represented by Formula 3, where 1 ⁇ is phenylene, and L 2 is a single bond, which may be prepared by the same method as in Scheme 2 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 or Banung Formula 2 by applying a counterungmul having a different substituent.
  • 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 is a first electrode; A crab 2 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 to provide an organic light emitting device. 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 and the like 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 injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting a hole may be represented by Formula 1 above.
  • 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 a layer for the electron transport and the electron injection pressure at the same time includes the 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 organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • 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.
  • the compound represented by Formula 1 may be included in the light emitting layer.
  • FIG. 2 shows an example of an organic light emitting element consisting 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.
  • the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer and the 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 according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a crab 2 electrode on a substrate.
  • an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting 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, spraying, 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, chromium, 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.
  • the negative electrode material an electron is easily injected into the organic material layer. It is preferable that it is a substance with a small work function.
  • the negative electrode material include metals such as magnesium, calcium, 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 the electrode, the hole injection material has the ability to transport holes to have a hole injection effect at the anode, has an excellent hole injection effect to the light emitting layer or the 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 include metal porphyrin, oligothiophene, arylamine-based organic matter, nucleonitrile-nuclear azatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone and 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.
  • a hole transporting material is a material capable of transporting holes from an anode or a hole injection layer to a light emitting layer. This is suitable.
  • the light emitting material is a material capable of emitting light and visible light by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and 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
  • heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and the styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are 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, but are not limited to these.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, kale, iterboom and samarium, each If this is followed by an aluminum or silver layer.
  • the electron injection layer is a layer for injecting electrons from an electrode, has an ability to transport electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and holes of excitons generated in the light emitting layer
  • the compound which prevents movement to an injection layer and is excellent in thin film formation ability is preferable.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methylquinolinato) (o-cresol Lato) gallium, bis (2-methyl-8-quinolinato) (1-naphlato) aluminum, bis (2-methyl-8-quinolinato) (2-naphlato) gallium, and the like It is not limited.
  • the organic light emitting device may be a top emission type, a bottom emission type or a double-sided emission type depending on 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 invention, the scope of the invention is limited by these no.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 A was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • 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 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.
  • Compound 1 prepared in Preparation Example 1 and the following compound [LiQ] (Lithiumquinolate) were vacuum-deposited in 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 a thickness of 1,000 A were sequentially deposited on the electron injection and transport layer to form a cathode.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using one of 2 to 5 compounds.
  • Example 1-1 except that Compound 1 (III), Compound (IV), or Compound (V) having the following structure was used as shown in Table 1 instead of Compound 1, in the same manner as in Example 1-1. An organic light emitting device was produced.
  • the driving voltage and the luminous efficiency were measured at a current density of 10 mA / cm 2 for the organic light emitting diodes manufactured in Examples 1-1 to 1-5 and Comparative Examples 1-1 to 1-5, 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. Table 1
  • the heterocyclic compound represented by the formula (1) having an asymmetric structure based on the binaphthalene skeleton bonded to each of the specific cyan group and the specific hetero ring according to the present invention is electron injection of the organic light emitting device And it can be seen that it can be used in the organic material layer capable of electron transport at the same time.
  • the heterocyclic compound represented by Formula 1 when it contains a benzimidazole group, it has a structure that does not include a CN functional group at the other end, it is possible to more easily control the electron transport capacity, band gap, energy level and thermal characteristics, thereby providing voltage, efficiency , It was confirmed that all of the superior characteristics in terms of life.
  • the heterocyclic compound represented by Formula 1 when used in an organic material layer capable of simultaneously injecting and transporting electrons, 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, methane, 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.
  • the electron The anode was formed by sequentially depositing lithium fluoride (LiF) and aluminum to a thickness of 1,000 A on the injection and transport layers sequentially.
  • An organic light emitting diode was manufactured according to the same method as Example 2-1 except for using one of 2 to 5 compounds.
  • An organic light emitting diode was manufactured according to the same method as Example 2-1 except for using Compound (1) or (II) having the following structure as described in Table 2 instead of Compound 1 in Example 2-1. .
  • Example 2-1 except that Compound (III), Compound (IV), or Compound (V) having the following structure was used as shown in Table 2 instead of Compound 1, in the same manner as in Example 2-1. An organic light emitting device was produced.

Landscapes

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

Abstract

La présente invention concerne un nouveau composé hétérocyclique et un élément électroluminescent organique le comprenant.
PCT/KR2018/006241 2017-05-31 2018-05-31 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant WO2018221986A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201880009529.6A CN110248928B (zh) 2017-05-31 2018-05-31 新型杂环化合物及利用其的有机发光元件

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR20170067649 2017-05-31
KR10-2017-0067649 2017-05-31
KR10-2018-0062155 2018-05-30
KR1020180062155A KR102064994B1 (ko) 2017-05-31 2018-05-30 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자

Publications (1)

Publication Number Publication Date
WO2018221986A1 true WO2018221986A1 (fr) 2018-12-06

Family

ID=64456471

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2018/006241 WO2018221986A1 (fr) 2017-05-31 2018-05-31 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant

Country Status (1)

Country Link
WO (1) WO2018221986A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007046658A1 (fr) * 2005-10-21 2007-04-26 Lg Chem. Ltd. Derives binaphtalene, procede d'elaboration et dispositif organique electronique l'utilisant
KR100967355B1 (ko) * 2009-11-03 2010-07-05 주식회사 유피케미칼 유기 전기 발광 소자용 재료 및 이를 이용한 유기 전기발광 소자
KR20120051598A (ko) * 2010-11-12 2012-05-22 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 전자 소자
KR20150003564A (ko) * 2013-07-01 2015-01-09 삼성디스플레이 주식회사 화합물 및 이를 포함한 유기 발광 소자
KR20150025259A (ko) * 2013-08-28 2015-03-10 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 (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2007046658A1 (fr) * 2005-10-21 2007-04-26 Lg Chem. Ltd. Derives binaphtalene, procede d'elaboration et dispositif organique electronique l'utilisant
KR100967355B1 (ko) * 2009-11-03 2010-07-05 주식회사 유피케미칼 유기 전기 발광 소자용 재료 및 이를 이용한 유기 전기발광 소자
KR20120051598A (ko) * 2010-11-12 2012-05-22 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기 전자 소자
KR20150003564A (ko) * 2013-07-01 2015-01-09 삼성디스플레이 주식회사 화합물 및 이를 포함한 유기 발광 소자
KR20150025259A (ko) * 2013-08-28 2015-03-10 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

Similar Documents

Publication Publication Date Title
CN107840835B (zh) 新的杂环化合物及利用它的有机发光元件
KR102017790B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
KR102064992B1 (ko) 신규한 헤테로고리 화합물 및 이를 이용한 유기발광 소자
KR102080289B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자
KR102080286B1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
KR102016081B1 (ko) 신규한 화합물 및 이를 포함하는 유기발광 소자
KR102235734B1 (ko) 신규한 화합물 및 이를 포함하는 유기발광 소자
KR20200026124A (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
KR102576227B1 (ko) 신규한 화합물 및 이를 포함하는 유기발광 소자
KR20190135398A (ko) 신규한 트리페닐렌 화합물 및 이를 이용한 유기 발광 소자
KR102064993B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
KR20200018322A (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자
KR102623893B1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
KR102175713B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
KR102235477B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자
KR102217268B1 (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
KR20200020582A (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
WO2018084426A1 (fr) Nouveau composé hétérocyclique et dispositif électroluminescent organique le comprenant
KR102064994B1 (ko) 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
KR102474920B1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
KR102202058B1 (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
KR102210699B1 (ko) 유기 발광 소자
KR20220040762A (ko) 신규한 화합물 및 이를 이용한 유기발광 소자
KR20210046231A (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자
KR20210046229A (ko) 신규한 화합물 및 이를 이용한 유기 발광 소자

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 18808694

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 18808694

Country of ref document: EP

Kind code of ref document: A1