WO2019216743A1 - Nouveau composé hétérocyclique et diode électroluminescente organique l'utilisant - Google Patents

Nouveau composé hétérocyclique et diode électroluminescente organique l'utilisant Download PDF

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WO2019216743A1
WO2019216743A1 PCT/KR2019/006002 KR2019006002W WO2019216743A1 WO 2019216743 A1 WO2019216743 A1 WO 2019216743A1 KR 2019006002 W KR2019006002 W KR 2019006002W WO 2019216743 A1 WO2019216743 A1 WO 2019216743A1
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group
substituted
unsubstituted
light emitting
compound
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PCT/KR2019/006002
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English (en)
Korean (ko)
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정민우
이동훈
장분재
이정하
한수진
박슬찬
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주식회사 엘지화학
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Priority claimed from KR1020190054491A external-priority patent/KR102147908B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201980005726.5A priority Critical patent/CN111344288B/zh
Publication of WO2019216743A1 publication Critical patent/WO2019216743A1/fr

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    • 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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
    • 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 heterocyclic compound and an organic light emitting device comprising the same.
  • 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 formed of a multi-layered structure composed of different materials.
  • the organic layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula (1).
  • At least one of 3 ⁇ 4 to 3 ⁇ 4 is
  • To 3 ⁇ 4 are each independently At least one of ⁇ is
  • 0 0 or £
  • 5 to 5 each independently represent a substituted or unsubstituted 0 6-60 aryl; 0 1-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted 0, ⁇ and 0, show 5 is adjacent to each other 2019/216743 1 »(: 1 ⁇ 1 ⁇ 2019/006002
  • Substituted or unsubstituted (: 6-60 arylten ; or 0 1-60 heteroarylene containing one or more heteroatoms selected from the group consisting of substituted 0 and unsubstituted,
  • 3 ⁇ 4 to 3 ⁇ 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted 0 1-60 alkyl; Substituted or unsubstituted 0 1-60 haloalkyl; Substituted or unsubstituted 0 1-60 alkoxy; Substituted or unsubstituted 0 1-60 haloalkoxy; Substituted or unsubstituted 0 3 -60 cycloalkyl; Substituted or unsubstituted 0 2-60 alkenyl; Substituted or unsubstituted aryl; Substituted or unsubstituted 0 6 -60 aryloxy; Or 0 ! -60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted and unsubstituted 0 and
  • 111 is an integer from 0 to 4,
  • 112 is an integer from 0 to 3
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by Chemical Formula 1. to provide.
  • 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.
  • 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 present invention provides a compound represented by Chemical Formula 1.
  • + means a bond connected to another substituent.
  • ⁇ substituted or unsubstituted '' is deuterium; Halogen group; Cyano group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; Alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxy group; Silyl group; Boron group; Alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine group; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl including one or more of 0 and o atoms, or
  • the biphenyl when “a substituent to which two or more substituents are linked" is a biphenyl group, the biphenyl may be interpreted as an aryl group substituted with one phenyl group or a substituent to which two phenyl groups are linked. Is not particularly limited, but is preferably 1 to 40.
  • the compound may be a compound having the following structure, but is not limited thereto. 2019/216743 1 »(: 1 ⁇ 1 ⁇ 2019/006002
  • the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms 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.
  • 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 is specifically trimethylsilyl group, triethylsilyl group, Butyl dimethyl silyl group, vinyl dimethyl silyl group, propyl dimethyl silyl group, triphenyl silyl group, diphenyl silyl group, phenyl silyl group and the like, but is not limited thereto. 2019/216743 1 »(: 1 ⁇ 1 ⁇ 2019/006002
  • the boron group is specifically trimethyl boron group, triethyl boron group, butyl dimethyl boron group, triphenyl boron group, phenyl boron group and the like, but is not limited thereto.
  • 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, 11-propyl, isopropyl, butyl, 11-butyl, isobutyl, ratchetbutyl, 3-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, 11 -Pentyl, isopentyl, neopentyl, kopentyl, nuclear chamber, 11-nuclear chamber, 1-methylpentyl, 2-methylpentyl, 4 -methyl- 2-pentyl, 3, 3-dimethylbutyl, 2-ethylbutyl, heptyl, II-heptyl, 1-methylnucleus, cyclopentylmethyl, cyclonuxylmethyl, octyl, -octyl, 1 6 generation_octyl, 1-methylheptyl,
  • the alkenyl group 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.
  • the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl,
  • 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.
  • the 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, peryleneyl group, chrysenyl group, or the like, but is not limited thereto.
  • heteroaryl is a heteroaryl containing one or more of 0, and £ as a dissimilar element, carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heteroaryl include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, acridil 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
  • Dibenzothiophene group benzofuranyl group, phenanthrosline group (6113111; 11101), isooxazolyl group, thiadiazolyl group, phenothiazinyl group, dibenzofuranyl group, and the like, but is not limited thereto.
  • 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 heteroaryl amine may be applied to the description of the aforementioned heteroaryl.
  • the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description of the aryl group described above may be applied.
  • the description of the aforementioned heteroaryl 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 heterocycle is not a monovalent group, and the description of the aforementioned heteroaryl may be applied except that two substituents are formed by bonding.
  • Show to 3 may be each independently a substituted or unsubstituted 0 6-60 aryl.
  • the Shows 3 and 3 may be phenyl.
  • Chemical Formula 1, I to each independently, a single bond; Or substituted or unsubstituted Ce-60 arylene.
  • Formula 1 may be any one of the compounds of Formulas 2 to 5. 2019/216743 1 »(: 1/10 ⁇ 019/006002
  • 4 and 5 are each independently, substituted or unsubstituted 0 6-60 aryl, or 4 and ⁇ 5 may be combined with groups adjacent to each other to form a condensed ring.
  • in Formula 1 may be a single bond, phenylene, pyridinediyl, biphenyldiyl, or naphthylene. 2019/216743 1 »(: 1/10 ⁇ 019/006002
  • the compound may be selected from the group consisting of the following compounds:
  • X is halogen and more preferably bromo or chloro.
  • the reaction is a Suzuki coupling reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be modified as known in the art.
  • the manufacturing method may be more specific in the production examples to be described later. 2019/216743 1 »(: 1 ⁇ 1 ⁇ 2019/006002
  • the present invention provides an organic light emitting device including the compound represented by Formula 1.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by Formula 1; to provide.
  • 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, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as the organic layer.
  • the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • 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 diode according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • the compound represented by Formula 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.
  • the compound represented by Formula 1 may be included in the light emitting layer.
  • 2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, an electron transport layer 8, an electron injection layer 9.
  • an organic light-emitting device composed of a cathode (4) is the hole injection layer, hole transport layer, electron 2019/216743 1 »(: 1 ⁇ 1 ⁇ 2019/006002
  • the organic material layer may include a light emitting layer, and the light emitting layer may include two or more host materials.
  • the two or more host materials may include a compound represented by Chemical Formula 1.
  • 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 second electrode on a substrate. At this time, such as sputtering or e-beam evaporat ion
  • 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 Chemical 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 and the like, but is not limited thereto. 2019/216743 1 »(: 1 ⁇ 1 ⁇ 2019/006002
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material 0 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
  • 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 ((1), indium zinc oxide (1 ⁇ 0); combinations of metals and oxides such as 3 ⁇ 40: hour or £ ⁇ 2 : ⁇ ; poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] ( ⁇ : For example, conductive polymers such as polypyrrole and polyaniline, etc., but are not limited thereto.
  • the material has a small work function to facilitate electron injection
  • specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead. Or an alloy thereof, a multi-layered material such as LiF / Al or Li3 ⁇ 4Ml, etc.
  • the hole injection layer is a layer for injecting holes from an electrode, As the particle material, it has the ability to transport holes, and has an effect of hole injection at the anode, excellent hole injection effect on the light emitting layer or light emitting material, and prevents the excitons generated in the light emitting layer from moving to the electron injection layer or electron injection material.
  • H0M0 highest occupied molecul ar orbital
  • the highest occupied molecul ar orbital (H0M0) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic matter.
  • H0M0 metal porphyr
  • oligothiophene oligothiophene
  • arylamine-based organic matter 2019/216743 1 »(: 1 ⁇ 1 ⁇ 2019/006002
  • 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 capable of transporting holes from the anode or the hole injection layer and transferring the holes to the light emitting layer. This is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • the light emitting material is a material capable of emitting light in the visible region 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.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Polymers of the poly (p-phenylene vinylene) (PPV) family; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • PV poly (p-phenylene vinylene)
  • 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. Specifically, there are anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like.
  • the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, as an aromatic amine derivative 2019/216743 1 »(: 1 ⁇ 1 ⁇ 2019/006002
  • bamboo aromatic ring derivative having a substituted or unsubstituted arylamino group examples include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and the styrylamine compound includes at least one of substituted or unsubstituted arylamines.
  • a substituent selected from one or two or more selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group is substituted or unsubstituted.
  • 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 a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do.
  • 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, calcium, etherboom and samarium, each followed by an aluminum layer or a silver layer.
  • the electron injection layer is a layer for injecting electrons from an electrode, has a capability of transporting electrons, has an electron injection effect from the cathode, an excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinatolium, 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 [biquinolina] SAT beryllium bis (10-hydroxybenzo [biquinolinato] zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (0-cresolato Gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, etc., but are not limited thereto.
  • the organic light emitting device according to the present invention 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.
  • Preparation of the compound represented by Chemical Formula 1 and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are only for illustrating the present invention, and the scope of the present invention is not limited thereto.
  • the compound was prepared in the same manner as in the method of preparing Compound 1, except that dibenzo [13, (1] furan-3-ylboronic acid was used instead of dibenzo [bifuran-4-ylboronic acid. 66%) was prepared.
  • the compound was prepared in the same manner as in the method for preparing compound 1 in Example 1, except that dibenzo [13, (1] thiophene-2-ylboronic acid was used instead of dibenzoby, ( 1] furan-4-ylboronic acid. 29%) was prepared.
  • a glass substrate coated with a thin film of I0 (indium tin oxide) having a thickness of 1,300 A was put 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 Mi 11 ipore Co. was used as distilled water.
  • the ultrasonic cleaning was performed twice with distilled water for 10 minutes. Distilled water 2019/216743 1 »(: 1 ⁇ 1 ⁇ 2019/006002
  • ultrasonic cleaning 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 bar-1 compound was thermally vacuum deposited to a thickness of 50 kPa on the 110 transparent electrode prepared as above to form a hole injection layer.
  • the following _1 compound was vacuum-deposited to a thickness of 250 to form a hole transport certificate on the hole injection layer
  • the following 1′-2 compound was vacuum deposited to a thickness of 50 particles on the hole transport layer to form an electron blocking layer.
  • Compound 1, the following X-1 compound, and phosphorescent dopant 61) -1 which were prepared in Example 1 as a light emitting layer on the electron blocking layer, were co-deposited at a weight ratio of 44:44:12 to form a light emitting layer having a thickness of 400 particles. .
  • the following £ 1 ⁇ 1 compound was vacuum deposited to a thickness of 250 shows to form an electron transport certificate, and the following seed compound and a needle were vacuum deposited on the electron transport layer at a weight ratio of 98: 2 to form an electron having a thickness of 100 shows.
  • An injection layer was formed. Aluminum was deposited on the electron injection layer to a thickness of 1000 particles to form a cathode.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1, except that Compound 1 of Example 1 was used instead of Compound 1 of Example 1 in Experimental Example 1.
  • the experimental examples and comparative experimental examples were measured voltage and efficiency at a current density of 11/011 2
  • Substrate 2 Anode

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Abstract

La présente invention concerne un nouveau composé hétérocyclique et une diode électroluminescente organique l'utilisant.
PCT/KR2019/006002 2018-05-11 2019-05-10 Nouveau composé hétérocyclique et diode électroluminescente organique l'utilisant WO2019216743A1 (fr)

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Citations (5)

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Publication number Priority date Publication date Assignee Title
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