WO2019045528A1 - Nouveau composé et dispositif électroluminescent organique l'utilisant - Google Patents

Nouveau composé et dispositif électroluminescent organique l'utilisant Download PDF

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WO2019045528A1
WO2019045528A1 PCT/KR2018/010166 KR2018010166W WO2019045528A1 WO 2019045528 A1 WO2019045528 A1 WO 2019045528A1 KR 2018010166 W KR2018010166 W KR 2018010166W WO 2019045528 A1 WO2019045528 A1 WO 2019045528A1
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group
compound
layer
light emitting
organic
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PCT/KR2018/010166
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English (en)
Korean (ko)
Inventor
정민우
강민영
박태윤
조성미
문정욱
이정하
채미영
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주식회사 엘지화학
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Priority claimed from KR1020180102994A external-priority patent/KR102121433B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to US16/624,202 priority Critical patent/US11380851B2/en
Priority to CN201880039547.9A priority patent/CN110770228B/zh
Publication of WO2019045528A1 publication Critical patent/WO2019045528A1/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
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • 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

  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent characteristics of brightness, driving voltage, and response speed, and much research is proceeding.
  • 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 material layer may have a multi-layered structure composed of different materials.
  • the organic material layer may include a hole injection layer, a hole injection layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula 1 or 2:
  • Xi to 3 ⁇ 4 is N or CH, at least one of 3 ⁇ 4 to 3 ⁇ 4 is N, Y is 0 or S,
  • L < 2 &gt are each independently a single bond; Or substituted or unsubstituted C 6 -
  • Ar is substituted or unsubstituted d-so alkyl; Substituted or unsubstituted d- 60 haloalkyl; Substituted or unsubstituted C 3 - 60 cycloalkyl; Substituted or unsubstituted C 6 -C 60 aryl; Or substituted or unsubstituted C 2 - 60 heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of N, O and S;
  • the present invention also provides a method of manufacturing a semiconductor device, A second electrode facing the first electrode; And one or more organic layers disposed between the first electrode and the ground electrode, wherein at least one of the organic layers includes a compound represented by Formula 1 or 2, to provide.
  • the compound represented by the above formula (1) or (2) can be used as a material for the organic material layer of the organic light emitting device, and can improve the efficiency, the driving voltage and / or the lifetime of the organic light emitting device.
  • Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4.
  • FIG. 2 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 Respectively.
  • ⁇ ⁇ means a bond connected to another substituent, and a single bond means a case where no additional atom exists in a portion represented by L 2 .
  • substituted or unsubstituted 1 refers to a hydrogen atom, a halogen atom, a cyano group, a nitrile group, a nitro group, a hydroxyl group, a carbonyl group, an ester group, an imide group, an amino group, a phosphine oxide group, An alkoxy group, an aryloxy group, an alkyloxy group, an aryloxy group, an aryloxy group, an aryloxy group, an aryloxy group, an aryloxy group, a silyl group, a boron group, an alkyl group, an aryl group, an aralkyl group, A heteroaryl group, an arylamine group, an arylphosphine group, or heteroaryl containing at least
  • the substituent 11 in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent in which two phenyl groups are connected.
  • the carbon number of the carbonyl group is not particularly limited, but it is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the ester group may be substituted with a straight-chain, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms in the ester group. Specifically, it may be a compound of the following structural formula.
  • the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms.
  • the compound may be a compound having the following structure, but is not limited thereto.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group Triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like, but are not limited thereto.
  • the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include a methyl group, an ethyl group, a propyl group, a n-propyl group, an isopropyl group, a butyl group, a n-butyl group, an isobutyl group, N-butyl, 1-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-pentyl, Methylheptyl, 2-ethylpentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, , 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylnucyl, 5-methylnucyl and the like.
  • the alkenyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms.
  • the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • aryl group is not particularly limited,
  • the aryl group may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto.
  • polycyclic aryl group examples include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.
  • a fluorenyl group may be substituted, and two substituents may form a spiro structure with each other. Wherein the fluorenyl group is substituted
  • the heteroaryl is a heteroaryl containing at least one of 0, N, Si and S as a hetero atom.
  • the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heteroaryl examples include, but are not limited to, thiophene, furane, pyrrolyl, imidazole, thiazole, oxazole, oxadiazole, triazole, pyridyl, A pyrazinyl group, an isoquinoline group, an indole group, a carbazole group, a pyrazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, Benzoimidazole group, benzothiazole group, benzothiazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, isoxazolyl group, thiadiazole group, A benzyl group, a benzyl group, a benz
  • the alkyl group in the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the alkyl group described above.
  • the heteroaryl among the heteroarylamines can be applied to the heteroaryl described above.
  • the alkenyl group in the aralkenyl group is the same as the above-mentioned alkenyl group.
  • the description of the aryl group described above can be applied except that arylene is a divalent group.
  • the description of the above-mentioned heteroaryl can be applied except that the heteroarylene is a divalent.
  • the description of the above-mentioned aryl group or cycloalkyl group can be applied except that the hydrocarbon ring is not a monovalent group and two substituents are bonded to each other.
  • the description of heteroaryl described above can be applied, except that the heterocycle is not monovalent and two substituents are bonded to each other.
  • the present invention provides a compound represented by the above formula (1) or (2). Also, the 3 ⁇ 4 to 3 ⁇ 4 may be N.
  • L 2 are each independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted biphenylene, a substituted or unsubstituted terphenylene, a substituted or unsubstituted naphthylene, Substituted or unsubstituted phenanthrenylene, substituted or unsubstituted anthracenylene, substituted or unsubstituted fluoranthenylene, substituted or unsubstituted triphenylenylene, substituted or unsubstituted pyrenylene, substituted or unsubstituted carbazole Substituted or unsubstituted fluorenylenes, or substituted or unsubstituted spiro-fluorenylenes.
  • l and L 2 can each independently be a single bond, phenylene, biphenylene, or terphenyleryrene. Specifically, for example, and L 2 may each independently be a single bond, or phenylene.
  • Ar is a substituted or unsubstituted C 6 - 20 aryl; Or C 2 - 20 heteroaryl containing 1 to 3 substituted or unsubstituted 0 or S heteroatoms.
  • Ar may be phenyl, or biphenyl.
  • Xi to Y and Ar are as defined in the above formulas (1) and (2).
  • the compound may be any one selected from the group consisting of the following compounds:
  • the compounds represented by the above general formulas (1) and (2) have a structure in which a nitrogen-containing 6-membered heteroaryl group is bonded to a biscarbazolyl group bonded at a specific position and has a structure linked to the 1-position of dibenzofuranyl / dibenzothiophenyl And an organic light emitting element employing the same can have a high efficiency, a low driving voltage, a high brightness, and a long life, as compared with an organic light emitting element employing a compound having a structure in which amino groups are connected to other positions of fluorene.
  • the compound represented by the above formula (1) or (2) can be prepared, for example, by the same method as the following formula (a) or (b) The above production method can be more specific in the production example to be described later.
  • Equations (a) and (b) above 3 ⁇ 4, 3 ⁇ 4 ⁇ , and L 2 are as defined above.
  • the reactants used in the above antimicrobial formulas a and b may be prepared by appropriately substituting the starting material according to the structure of the compound to be produced in the present invention. Meanwhile, the present invention provides an organic light emitting device comprising a compound represented by the above formula (1) or (2).
  • the present invention provides a display device comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer contains a compound represented by the general formula (1) or (2) Lt; / RTI >
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multi-layer structure in which two or more layers and an organic material layer are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, an electron injecting layer, and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • 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.
  • a hole injection layer and a hole transporting layer between the first electrode and the light emitting layer, and an electron transporting layer and an electron injecting layer between the light emitting layer and the second electrode are further included .
  • ≪ / RTI &gt the structure of the organic light emitting device is not limited thereto, and may include fewer or more organic layers.
  • the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, at least one organic layer, 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 an anode, one or more organic compound layers and an anode are sequentially stacked on a substrate.
  • FIGS. Fig. 1 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a light emitting layer 3 and a cathode 4.
  • the compound represented by Formula 1 or 2 may be included in the light emitting layer.
  • 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.
  • the compound represented by Formula 1 or 2 may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.
  • the organic light emitting device according to the present invention May be prepared by materials and methods known in the art, except for including the compound represented by Formula (1) or (2).
  • the organic light emitting diode when the organic light emitting diode includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.
  • the organic light emitting device according to the present invention can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a metal oxide or a metal oxide having conductivity or an alloy thereof may be formed on the substrate by a PVD (physi cal vapor deposition) method such as a sputtering method or an e-beam evaporation method Depositing a cathode, forming an anode, forming an organic layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the anode, and depositing a material usable as a cathode thereon.
  • a PVD physi cal vapor deposition
  • the compound represented by Formula 1 or 2 may be formed into an organic layer by a solution coating method as well as a vacuum evaporation method in manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, ink jet printing, screen printing, spraying, coating, and the like, but is not limited thereto.
  • an organic light emitting device can be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (TO 2003/012890).
  • 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 and the second electrode is a cathode.
  • the anode material a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer.
  • the positive electrode material examples include vanadium, Metals such as chromium, copper, zinc and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ⁇ 0: ⁇ 1 SN0 or 2: a combination of a metal and an oxide such as Sb; And conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene KPEDOT), polypyrrole and polyaniline.
  • the negative electrode material is preferably 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, calcium, sodium, potassium, titanium, indium, yttrium lithium, gadolinium aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but the present invention is not limited thereto.
  • the hole injecting layer is a layer for injecting holes from an electrode.
  • the hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material.
  • a compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable.
  • the highest occupied molecular orbital (H0M0) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer.
  • the hole injecting material include organic materials such as porphyrin, oligothiophene, arylamine-based organic materials, quinacridone-based tetraphenylene-based organic materials, quinacridone-based organic materials, perylene ) Organic materials, anthraquinone, polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
  • the material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, But is not limited thereto.
  • the light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence.
  • the light emitting layer may include a host material and a dopant material as described above.
  • the host material may further include a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivative examples include an anthracene derivative pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound and the like.
  • heterocycle-containing compound examples include carbazole derivatives, dibenzofuran derivatives, Compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, such as pyrene, anthracenecyclycene and peripherrhene having an arylamino group.
  • arylamino groups such as pyrene, anthracenecyclycene and peripherrhene having an arylamino group.
  • the styrylamine compound include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted.
  • the electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Suitable. Specific examples include the A1 complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transporting layer can be used with any desired cathode material as used according to the prior art.
  • a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
  • the electron injection layer is a layer for injecting electrons from the electrode.
  • the electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material. A compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A nitrogen-containing 5-membered ring derivative, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) (2-methyl-8-quinolinato) (2-naphthalato) gallium, and the like But is not limited thereto.
  • the organic light emitting device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
  • the compound represented by Formula 1 or 2 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • the preparation of the compound represented by the above formula (1) or (2) and the organic light emitting device comprising 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.
  • N-cyanobenzimidamide (16.8 g, 114 mmol) and Compound A-2 (23 g, 114 mmol) and phosphrous oxychloride (12 mL, 128 mmol) were added to 500 mL of acetonitrile and stirred for 1 hour. After cooling to room temperature, the resulting solid was filtered, washed with water and ethanol, and dried to give Compound A. (29.2 g, 80% yield)
  • the glass substrate coated with thin ITO (indium tin oxide) film with a thickness of 1, 300 A was washed with ultrasonic waves in distilled water containing detergent.
  • a detergent a product of Fi Scher Co. was used, and distilled water, which was filtered with a filter (Fi lter) manufactured by Mi 11 ipore Co., was used as distilled water.
  • the ITO was washed for 30 minutes, then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner.
  • the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
  • the following HI-1 compound was thermally vacuum-deposited on the? -Transparent electrode prepared above to a thickness of 50 A to form a hole injection layer.
  • the HT-1 compound was thermally vacuum-deposited on the HTL to form a hole transport layer, and an HT-2 compound was vacuum deposited on the HT-1 deposited layer to a thickness of 50 A to form an electron blocking layer.
  • the phosphorescent dopant GD-1 was vacuum deposited on the HT-2 deposited film at a weight ratio of 10% to the phosphor host using Compound 1 synthesized in Preparation Example 2 at a weight ratio of 90) to the phosphorescent host.
  • An ET-1 material was vacuum deposited on the light emitting layer to a thickness of 250 A
  • the ET-2 material was co-deposited with Li at a weight ratio of 2% to a thickness of 100 A to form an electron transport layer and an electron injection layer.
  • Aluminum was deposited on the electron injection layer to a thickness of 1000 A to form a cathode.
  • Example 2 A device of Example 2 was fabricated in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 in Example 1.
  • Example 3 A device of Example 2 was fabricated in the same manner as in Example 1, except that Compound 2 was used instead of Compound 1 in Example 1.
  • Example 3 A device of Example 3 was fabricated in the same manner as in Example 1, except that Compound 3 was used instead of Compound 1 in Example 1.
  • a comparative element was prepared using the same method as in Example 1, except that the compounds A to C were used instead of the compound 1 in Example 1 above.
  • the host material compounds A to C used in the comparative example are as follows.
  • T95 means the time required for the luminance to be reduced to 95% when the initial luminance at a light density of 20 mA / cm 2 is taken as 100%.
  • Example 2 Compound 2 3.12 63.5 (0.322 '0.630) 40.3
  • Example 3 Compound 3 3.20 65.1 (0.321, 0.631) 50.0 Comparative Example 1 Compound A 3.21. 60.3 (0.321, 0.630) 25.0 Comparative Example 2 Compound B 3.33 59.8 (0.320, 0.629) 23.1 Comparative Example 3 Compound C 3.59 49.1 (0.339, 0.631) 5.1

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique l'utilisant.
PCT/KR2018/010166 2017-09-01 2018-08-31 Nouveau composé et dispositif électroluminescent organique l'utilisant WO2019045528A1 (fr)

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US16/624,202 US11380851B2 (en) 2017-09-01 2018-08-31 Compound and organic light emitting device comprising the same
CN201880039547.9A CN110770228B (zh) 2017-09-01 2018-08-31 新化合物和包含其的有机发光器件

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KR20170112077 2017-09-01
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KR1020180102994A KR102121433B1 (ko) 2017-09-01 2018-08-30 신규한 화합물 및 이를 이용한 유기발광 소자
KR10-2018-0102994 2018-08-30

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Citations (6)

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