WO2020159128A1 - Dispositif électroluminescent organique - Google Patents

Dispositif électroluminescent organique Download PDF

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WO2020159128A1
WO2020159128A1 PCT/KR2020/000878 KR2020000878W WO2020159128A1 WO 2020159128 A1 WO2020159128 A1 WO 2020159128A1 KR 2020000878 W KR2020000878 W KR 2020000878W WO 2020159128 A1 WO2020159128 A1 WO 2020159128A1
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group
light emitting
compound
transport layer
organic light
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PCT/KR2020/000878
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English (en)
Korean (ko)
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이재구
송동근
노지영
차용범
이우철
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주식회사 엘지화학
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Priority claimed from KR1020200002772A external-priority patent/KR20200093442A/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to US17/294,277 priority Critical patent/US11950440B2/en
Priority to CN202080006109.XA priority patent/CN112997336B/zh
Publication of WO2020159128A1 publication Critical patent/WO2020159128A1/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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present invention relates to an organic light emitting device having a low driving voltage, high luminous efficiency and long life characteristics.
  • the organic light emitting phenomenon refers to a phenomenon that converts 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, and fast response time, and has excellent luminance, driving voltage, and response speed characteristics, and thus many studies have been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode.
  • the organic material layer is often formed of a multi-layered structure composed of different materials, for example, may be formed of 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 1 Korean Patent Publication No. 10-2000-0051826
  • the present invention is to provide an organic light emitting device having a low driving voltage, high luminous efficiency and long life characteristics.
  • the present invention provides the following organic light emitting device:
  • the light emitting layer includes a host and a dopant
  • the difference between the dipole moment value of the compound contained in the hole transport layer and the dipole moment value of the host is 1.0 to 2.0
  • the organic light emitting device can have a low driving voltage, high luminous efficiency, and long life characteristics by using a material of a host and a hole transport layer that satisfies a specific dipole moment value.
  • FIG. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4 and a cathode 5.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 6, a second hole transport layer 7, a first hole transport layer 8, a light emitting layer 4, an electron injection and transport layer 9, and An example of an organic light emitting device made of the cathode 5 is shown.
  • substituted or unsubstituted in this specification is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxy group; Carbonyl group; Ester groups; Imide group; Amino group; Phosphine oxide group; Alkoxy groups; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy group; Aryl sulfoxyl group; Silyl group; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl group; Aryl group; Aralkyl group; An alkenyl group; Alkyl aryl groups; Alkylamine groups; Aralkylamine group; Heteroarylamine group; Arylamine group; Arylphosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituents
  • the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably 1 to 40 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the oxygen of 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. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • the number of carbon atoms of the imide group is not particularly limited, but is preferably 1 to 25 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the silyl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc. However, it is not limited thereto.
  • the boron group is specifically a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a 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 straight chain or branched chain, and 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, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the carbon number of the alkenyl group is 2 to 20. 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, steelbenyl 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 an exemplary 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 is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., as a monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a 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 combine with each other to form a spiro structure.
  • the fluorenyl group When the fluorenyl group is substituted, It can be back. However, it is not limited thereto.
  • the heterocyclic group is a heterocyclic group containing one or more of O, N, Si and S as heterogeneous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • the heterocyclic group include thiophene group, furan group, pyrrol 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, pyridopyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole
  • an aryl group in an aralkyl group, an alkenyl group, an alkylaryl group, and an arylamine group is the same as the exemplified aryl group.
  • the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-described alkyl group.
  • heteroarylamine among heteroarylamines may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group among the alkenyl groups is the same as the exemplified alkenyl group.
  • the description of the aryl group described above may be applied, except that the arylene is a divalent group.
  • the description of the heterocyclic group described above may be applied, except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and a description of the aryl group or cycloalkyl group described above may be applied, except that two substituents are formed by bonding.
  • the heterocycle is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied, except that two substituents are formed by bonding.
  • the present invention the anode; Hole transport layer; Emitting layer; And a cathode, wherein the light emitting layer includes a host and a dopant, and the difference between the dipole moment value of the compound included in the hole transport layer and the dipole moment value of the host is a specific range. Is done.
  • the hole transport layer and the light emitting layer are adjacent.
  • dipole moment refers to a physical quantity indicating the degree of polarity, and may be calculated as in Equation 1 below.
  • the molecular density can be calculated by calculating the dipole moment value.
  • the molecular density can be obtained by calculating the charge and dipole for each atom using the Hirshfeld Charge Analysis method, and calculating it according to the following equation. Dipole Moment).
  • the difference between the dipole moment value of the host compound of the light emitting layer and the dipole moment value of the compound included in the hole transport layer should be considered.
  • the dipole moment value of the host and the hole transport layer When the difference in the dipole moment value of the compound contained in the specific range, it was confirmed that it may have high luminous efficiency characteristics.
  • the difference between the dipole moment value of the host and the dipole moment value of the compound included in the hole transport layer may be 1.0 to 2.0.
  • the organic light emitting device When the difference in the dipole moment value is less than 1.0, the organic light emitting device has a disadvantage of low efficiency, and when it exceeds 2.0, there is a problem that efficiency decreases.
  • the dipole moment value of the compound included in the hole transport layer may be 1.0 to 3.0, and preferably, it may be 1.2 to 3.0, or 1.2 to 2.8.
  • the dipole moment value of the host may be 0.1 to 1.2, preferably, 0.15 to 1.2, or 0.15 to 1.0.
  • the hole transport layer is a layer that receives holes from the hole injection layer, which will be described later, and transports holes from the hole injection layer to the light emitting layer. It is a hole transport material that transports holes from the anode or the hole injection layer and transports holes to the light emitting layer. Large materials are suitable.
  • the hole transport layer may include a compound represented by Formula 1 below:
  • R 1 and R 2 are each independently hydrogen; Or substituted or unsubstituted C 6-60 aryl,
  • Ar 1 is phenyl, biphenyl-2-yl, biphenyl-4-yl, naphthyl, phenanthrenyl, or naphthyl phenyl,
  • Ar 2 is phenyl, biphenyl-4-yl, naphthyl, phenanthrenyl, naphthyl phenyl, phenanthrenyl phenyl, 9,9-dimethyl-9H-fluorenyl, 9,9-diphenyl-9H-flu Orenyl, or 9,9'-spirobifluorenyl, , , or to be.
  • Chemical Formula 1 may be represented by Chemical Formula 1-1 or Chemical Formula 1-2:
  • R 1 , R 2 , Ar 1 and Ar 2 are as defined in Formula 1 above.
  • R 1 and R 2 are each independently hydrogen; Or substituted or unsubstituted C 6-30 aryl,
  • R 1 and R 2 are each independently hydrogen, phenyl, or naphthyl.
  • Ar 2 is phenyl, biphenyl-4-yl, naphthyl phenyl, phenanthrenyl phenyl, 9,9-dimethyl-9H-fluorenyl, 9,9-diphenyl-9H-fluorenyl, or 9,9'-spirobifluorenyl, , , or to be.
  • the compound represented by Formula 1 may be prepared by the same method as in Scheme 1 below, and other compounds may be similarly prepared.
  • X 1 is halogen, and more preferably bromo or chloro.
  • Reaction Scheme 1 is an amine substitution reaction, preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be modified as known in the art.
  • the manufacturing method may be more specific in the manufacturing examples to be described later.
  • the organic light emitting device may include an additional hole transport layer in addition to the hole transport layer described above.
  • an additional hole transport layer is included as a layer not adjacent to the light emitting layer.
  • the additional hole transport layer can be used without limitation the hole transport layer used in the technical field belonging to the present invention, specifically include arylamine-based organic materials, conductive polymers and block copolymers having conjugated and non-conjugated parts together Can.
  • the dopant material used in the light emitting layer is not particularly limited as long as it is used in an organic light emitting device, and for example, the dopant material includes an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, and includes pyrene, anthracene, chrysene, periplanene, etc. having an arylamino group, and substituted or unsubstituted as a styrylamine compound.
  • a compound in which at least one arylvinyl group is substituted with the arylamine, a substituent selected from 1 or 2 or more 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.
  • a substituent selected from 1 or 2 or more 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.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like but are not limited thereto.
  • metal complexes include, but are not limited to, iridium complexes, platinum complexes, and the like.
  • a compound represented by the following Chemical Formula 2 may be used as the host:
  • R 3 is hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
  • Ar 3 and Ar 4 are each independently, substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
  • L 1 and L 2 are each independently a single bond; Substituted or unsubstituted C 6-60 arylene; Or C 2-60 heteroarylene containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S.
  • R 3 is hydrogen; Substituted or unsubstituted C 6-30 aryl; Or C 6-30 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
  • R 3 is phenyl, biphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, phenyl carbazolyl, or naphthyl phenyl,
  • R 3 is phenyl, biphenylyl, naphthyl, dibenzofuranyl, dibenzothiophenyl, 9-phenyl-9H-carbazolyl, or naphthyl phenyl.
  • Ar 3 and Ar 4 are each independently, substituted or unsubstituted C 6-30 aryl; Or C 6-30 heteroaryl containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
  • Ar 3 and Ar 4 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, binaphthylyl, naphthyl phenyl, phenanthrenyl phenyl, phenyl naphthyl, di Benzofuranyl, dibenzothiophenyl, benzonaphthofuranyl, or benzonaphthothiophenyl,
  • Ar 3 and Ar 4 are each independently phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, vinaphthylyl, naphthyl phenyl, phenanthrenyl phenyl, phenyl naphthyl, di Benzofuranyl, dibenzothiophenyl, benzo[d]naphtho[1,2-b]furanyl, benzo[d]naphtho[2,3-b]furanyl, benzo[d]naphtho[2, 1-b]furanyl, benzo[d]naphtho[1,2-b]thiophenyl, benzo[d]naphtho[2,3-b]thiophenyl, or benzo[d]naphtho[2,1 -b]thiophenyl.
  • L 1 and L 2 are each independently a single bond; Substituted or unsubstituted C 6-30 arylene; Or C 6-30 heteroarylene containing any one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
  • L 1 and L 2 are each independently a single bond, phenylene, biphenylene, naphthylene, dibenzofuranylene, or dibenzothiophenylene.
  • the compound represented by the formula (2) is, for example, may be prepared by a production method such as the following scheme 2-1 or 2-2, and other compounds may be similarly prepared.
  • X 2 to X 4 in Reaction Schemes 2-1 and 2-2 are as defined above, and X 2 to X 4 are each independently halogen, and more preferably each independently bromo or chloro. .
  • Reaction Scheme 2-1 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.
  • Reaction Scheme 2-2 is a ketone addition reaction and a removal reaction, and the reactor, catalyst, solvent, and the like used may be appropriately changed to a desired product.
  • the manufacturing method may be more specific in the manufacturing examples to be described later.
  • the organic light emitting devices other than the above-described light emitting layer and the hole transport layer are not particularly limited as long as they can be used in the organic light emitting device, and will be described below for each configuration.
  • the positive electrode material is preferably a material having a large work function so that hole injection into the organic material layer is smooth.
  • 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 (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO:Al or SnO 2 :Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.
  • the cathode material is preferably a material having a small work function to facilitate electron injection into an 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;
  • a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the organic light emitting device may include a hole injection layer for injecting holes from an electrode.
  • the hole injection material it has the ability to transport holes and has a hole injection effect at the anode, an excellent hole injection effect for the light emitting layer or the light emitting material, and prevents the movement of the exciton generated in the light emitting layer to the electron injection layer or the electron injection material
  • a compound excellent in the ability to form a thin film is preferred.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • the hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances.
  • the organic light emitting device may include an electron transport layer that transports electrons from the cathode or the electron injection layer to the electron control layer by receiving electrons.
  • the electron transport material a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons is suitable.
  • Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used according to the prior art.
  • suitable cathode materials are conventional materials that have a low work function and are followed by an aluminum or silver layer. Specifically, cesium, barium, calcium, ytterbium and samarium, followed by an aluminum layer or a silver layer in each case.
  • the organic light emitting device may include an electron injection layer that injects electrons from an electrode.
  • an electron injection material it has the ability to transport electrons, has an electron injection effect from the cathode, an excellent electron injection effect for the light emitting layer or the light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also , A compound having excellent thin film forming ability is preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, 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-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-methyl-8-quinolinato)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
  • FIGS. 1 and 2 The structure of the organic light emitting device according to the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting device comprising a substrate 1, an anode 2, a hole transport layer 3, a light emitting layer 4 and a cathode 5.
  • the organic light emitting device can be manufactured by sequentially stacking the above-described components.
  • a positive electrode is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
  • PVD physical vapor deposition
  • an organic material layer including a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and a material that can be used as a cathode is deposited thereon.
  • an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the light emitting layer may be formed by a host and a dopant by a vacuum deposition method as well as a solution coating method.
  • the solution application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate (WO 2003/012890).
  • the manufacturing method is not limited thereto.
  • the organic light emitting device may be a front emission type, a back emission type or a double-sided emission type depending on the material used.
  • phenyl bromide (1 eq) was dissolved in tetrahydrofuran, and n-BuLi (1.1 eq) was slowly added dropwise at -78°C. After 30 minutes 2-(naphthalen-1-yl)anthracene-9,10-dione (1 eq) was added. After raising the temperature to room temperature, when the reaction was completed, it was extracted with ethyl acetate and washed with water. The above and the method were performed once more using phenyl bromide. After the reaction was completed, the mixture was extracted with ethyl acetate and washed with water.
  • a glass substrate (corning 7059 glass) coated with a thin film of indium tin oxide (ITO) at a thickness of 1000 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer Co. was used as the detergent, and Millipore Co. was used as the distilled water. Distilled water filtered secondarily was used as a filter of the product. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent such as isopropyl alcohol, acetone, or methanol, and then dried and transferred to a plasma cleaner. In addition, the substrate was dry-cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.
  • ITO indium tin oxide
  • a compound of the following compound HT1 and the following compound HI1 was thermally vacuum-deposited to a thickness of 100 Pa to a molar ratio of 98:2 to form a hole injection layer.
  • a common hole transport layer (the second hole transport layer) was formed by vacuum-depositing the compound represented by the following compound HT1 (1150 ⁇ ) on the hole injection layer.
  • Compound 1 prepared above was vacuum deposited on the common hole transport layer (second hole transport layer) to form a blue hole transport layer (first hole transport layer) with a thickness of 50 mm 2.
  • the following compound BD was vacuum-deposited in a weight ratio of 25:1 to form a light emitting layer.
  • the following compound ET1 and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 310 MPa.
  • lithium fluoride (LiF) with a thickness of 12 ⁇ and aluminum with a thickness of 1,000 ⁇ were sequentially deposited to form a negative electrode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 2 ⁇ /sec
  • the lithium fluoride of the negative electrode was maintained at a rate of 0.5 ⁇ /sec
  • the aluminum was maintained at a deposition rate of 2 ⁇ /sec
  • the vacuum degree during deposition was 2x10 -7.
  • An organic light emitting device was manufactured by maintaining ⁇ 5x10 -6 torr.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 below was used instead of Compound 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 below was used instead of Compound 1.
  • Compounds A to F described in Table 1 are as follows.
  • the luminous efficiency of the organic light emitting device manufactured in the above Examples and Comparative Examples was measured at a current density of 10 mA/cm 2 .
  • the results are shown in Table 1 below, and the dipole moment values of the compounds used in the host and hole transport layers are also shown.
  • substrate 2 anode
  • hole transport layer 4 light emitting layer
  • Second hole transport layer 8 First hole transport layer

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Abstract

L'invention concerne un dispositif électroluminescent organique comprenant une anode, une couche de transport de trous, une couche d'émission et une cathode, la couche d'émission comprenant un hôte et un dopant, et la différence entre la valeur de moment dipolaire d'un composé inclus dans la couche de transport de trous et la valeur de moment dipolaire de l'hôte est de 1,0 à 2,0.
PCT/KR2020/000878 2019-01-28 2020-01-17 Dispositif électroluminescent organique WO2020159128A1 (fr)

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US17/294,277 US11950440B2 (en) 2019-01-28 2020-01-17 Organic light emitting device
CN202080006109.XA CN112997336B (zh) 2019-01-28 2020-01-17 有机发光器件

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Citations (5)

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US20020127427A1 (en) * 2001-01-02 2002-09-12 Eastman Kodak Company Organic light emitting diode devices with improved luminance efficiency
JP2014013933A (ja) * 2003-10-27 2014-01-23 Semiconductor Energy Lab Co Ltd 発光素子
JP2015037168A (ja) * 2013-08-16 2015-02-23 昭和電工株式会社 有機発光素子
KR20180044821A (ko) * 2016-10-24 2018-05-03 노발레드 게엠베하 유기 발광 다이오드용 전자 수송층 스택
KR101907750B1 (ko) * 2015-09-25 2018-10-15 주식회사 엘지화학 유기 발광 소자

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020127427A1 (en) * 2001-01-02 2002-09-12 Eastman Kodak Company Organic light emitting diode devices with improved luminance efficiency
JP2014013933A (ja) * 2003-10-27 2014-01-23 Semiconductor Energy Lab Co Ltd 発光素子
JP2015037168A (ja) * 2013-08-16 2015-02-23 昭和電工株式会社 有機発光素子
KR101907750B1 (ko) * 2015-09-25 2018-10-15 주식회사 엘지화학 유기 발광 소자
KR20180044821A (ko) * 2016-10-24 2018-05-03 노발레드 게엠베하 유기 발광 다이오드용 전자 수송층 스택

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