WO2019083122A1 - Nouveau composé et élément électroluminescent organique l'utilisant - Google Patents

Nouveau composé et élément électroluminescent organique l'utilisant

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Publication number
WO2019083122A1
WO2019083122A1 PCT/KR2018/007716 KR2018007716W WO2019083122A1 WO 2019083122 A1 WO2019083122 A1 WO 2019083122A1 KR 2018007716 W KR2018007716 W KR 2018007716W WO 2019083122 A1 WO2019083122 A1 WO 2019083122A1
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compound
group
substituted
unsubstituted
layer
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PCT/KR2018/007716
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English (en)
Korean (ko)
Inventor
하재승
이성재
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LG Chem Ltd
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LG Chem Ltd
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Priority claimed from KR1020180062160A external-priority patent/KR102142676B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to CN201880043029.4A priority Critical patent/CN110799487B/zh
Publication of WO2019083122A1 publication Critical patent/WO2019083122A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • organic light 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 luminance, 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-layer structure composed of different materials.
  • the organic material layer may include a hole injection layer, a hole transport 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.
  • Li and L < 2 > are each independently a single bond; Substituted or unsubstituted C 6 - 60 arylene; Or substituted or unsubstituted C 2 - 60 heteroarylene containing at least one hetero atom selected from the group consisting of N, O, and S,
  • Ri to R 5 are each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, substituted or unsubstituted d-60 alkyl, substituted or unsubstituted d-60 alkoxy, substituted or unsubstituted d- unsubstituted C 3 - 60 cycloalkyl, substituted or unsubstituted C 6 - 60 aryl, or tri (d-60 alkyl) silyl, and,
  • a to e are each independently an integer of 0 to 3
  • Ar represents a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted quaterphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenan Thienyl, substituted or unsubstituted triphenylenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted Dibenzothiophenyl, or a substituent represented by the following formula (2) or
  • R 6 and R 7 each independently is C o alkyl, or 3 ⁇ 4 and 3 ⁇ 4 are bonded to each other C 3
  • 3 ⁇ 4 and 3 ⁇ 4 are each independently C 6 - 60 aryl
  • the present invention also relates to a plasma display panel comprising a first electrode; A second electrode facing 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 includes a compound represented by Formula 1 do.
  • the compound represented by the general formula (1) can be used as a material of an organic material layer of an organic light emitting device and can improve the efficiency, the driving voltage and / or the lifetime of the organic light emitting device.
  • the compound represented by Formula 1 can be used as a hole injecting, hole transporting, hole injecting and transporting, light emitting, electron transporting, or electron injecting material.
  • FIG. 1 is a schematic diagram of an organic electroluminescent device comprising a substrate 1, an anode 2, a light emitting layer 3, And shows an example of a light emitting device.
  • FIG. 2 shows an example of an organic light emitting element made up of 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 .
  • the present invention provides a compound represented by the above formula (1).
  • S means a bond connected to another substituent.
  • the "substituent group to which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, and 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, 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 exemplified by a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, 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 methyl, ethyl, propyl n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert- butyl, sec- Pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, heptyl, heptyl, heptyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, But are not limited to, 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.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms.
  • the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3- 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto.
  • 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. 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 be bonded to each other to form a spiro structure. When the fluorenyl group is substituted,
  • the heterocyclic group is a heterocyclic group containing at least one of 0, N, Si and S as a hetero atom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic group examples include a thiophene group, a furan group, a pyrrolyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a pyrimidyl group, , A pyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyranyl group, a pyrazinopyranyl group, an isoquinoline group, , carbazole group, benzoxazole group, a benzo imidazole benzothiazolyl group, a benzo carbazole, benzothiophene group,
  • the aryl group in the aralkyl group, the aralkenyl group, the alkylaryl group and the arylamine group is the same as the aforementioned aryl group.
  • 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 aforementioned heterocyclic group.
  • 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 heterocyclic group can be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent hydrocarbon ring, and the hydrocarbon ring is not a monovalent hydrocarbon ring, Can be applied.
  • the description of the above-mentioned heterocyclic group can be applied except that the heterocyclic ring is not a monovalent group and two substituents are bonded to each other.
  • L 2 -Ar when the structure of L 2 -Ar is phenyl or biphenylyl, R 1 is not a single bond.
  • the structure of -L 2 -Ar is phenyl or biphenyl, when L 2 is a single bond and Ar is phenyl; When L < 2 > is a single bond and Ar is biphenyl; Or when L < 2 > is phenylene and Ar is phenyl. More preferably, when the structure of L < 2 > -Ar is phenyl or biphenylyl, it is phenylene.
  • R 6 and R 7 are methyl, or R 6 and R 7 are bonded to each other to form a cyclopentane, or a cyclic nucleic acid ring.
  • Ar is selected from the group consisting of phenyl, biphenyl, terphenyl, quaterphenyl, naphthyl, phenanthrenyl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, Which one is:
  • the present invention provides a liquid crystal display comprising: a first electrode; The first electrode A second electrode facing the first electrode; And one or more organic layers disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a compound represented by Formula 1 do.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as organic layers.
  • the organic material layer may include a hole injecting layer, a hole transporting layer, or a layer simultaneously injecting and transporting holes, and the hole injecting layer, the hole transporting layer, And a compound to be displayed.
  • the organic layer may include a light emitting layer, and the light emitting layer includes a compound represented by the general formula (1).
  • the compound according to the present invention can be used as a dopant in a light emitting layer.
  • the organic material layer may include an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer includes the compound represented by the above formula (1).
  • the electron transporting layer, the electron injecting layer, or the layer which simultaneously transports electrons and injects electrons includes the compound represented by the above formula (1).
  • the organic material layer may include a light emitting layer and an electron transporting layer, and the electron transporting layer may include a compound represented by the general formula (1).
  • the organic light emitting device according to the present invention may be a normal type organic light emitting device in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an inverted type organic light emitting device in which 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 device comprising 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 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 compounds represented by the above-mentioned Formula 1 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 can be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by the above formula (1).
  • 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 layer, and a second electrode on a substrate.
  • a metal oxide or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a PVDCphysi cal Vapor Deposition method such as a sputtering method or an electron beam evaporation method, A hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer And then depositing a material that can be used as a cathode on the organic layer.
  • a PVDCphysi cal Vapor Deposition method such as a sputtering method or an electron beam evaporation method, A hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer And then depositing a material that can be used as a cathode on the organic layer.
  • an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of 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 (WO 2003/012890). However, the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode 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 to 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 (ITO), and indium zinc oxide (IZO); ⁇ 0: ⁇ 1 SN0 or 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] It is not.
  • 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 magnesium, fowl, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, Metals such as 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 HOMOChighest occupying molecule 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 metal porphyrin, oligothiophene, arylamine-based organic materials, nucleantitrile-tetra-phenylene-based organic materials, quinacridone-based organic materials, perylene perylene-based 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 and is capable of transporting holes from the anode or the hole injection layer to the light emitting layer as a hole transport material. Suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are 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 comprise a host material and a scrim material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds.
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • splittable 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, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group.
  • 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. Do. 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.
  • An example of a suitable cathode material is a conventional material with a low work function followed by an aluminum or 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 complex compound and a nitrogen-containing 5-membered ring derivative, 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) chlorogallium, bis (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 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
  • the preparation of the compound represented by Formula 1 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.
  • triphenylene-2-ylboronic acid was used instead of 2-bromotriphenylene and 2,6-bromonaphthalene was used in place of 4-chlorophenylboronic acid.
  • Compound A3 was prepared.
  • Compound A5 was prepared in the same manner except that 2-chlorophenylboronic acid was used instead of 4-chlorophenylboronic acid in the preparation of Compound A1.
  • Compound B2 was prepared in the same manner as Compound B1, except that Compound A2 was used instead of 2-bromotriphenylene.
  • Compound B3 was prepared in the same manner as in the preparation of Compound B1, except that aniline was used instead of 2-bromotriphenylene
  • Compound 1 was prepared in the same manner as Compound B1, except that 2-bromotriphenylene was used in an amount of 2-fold.
  • Compound 5 was prepared in the same manner as in the preparation of Compound 2, except that 1- (4-chlorophenyl) naphthalene was used instead of 2-bromo-9,9-dimethyl-9H-fluorene.
  • Compound 6 was prepared in the same manner as in the preparation of Compound 2, except that 1- (4-chlorophenyl) phenanthrene was used instead of 2-bromo-9,9-dimethyl-9H-fluorene.
  • Compound 7 was prepared in the same manner as Compound 2 except that Compound B2 was used instead of Compound B1 and 4-bromobiphenyl was used instead of 2-bromo-9,9-dimethyl-9H-fluorene Respectively.
  • Compound 8 was prepared in the same manner as Compound 2, except that Compound B2 was used instead of Compound B1.
  • Compound 9 was prepared in the same manner as in the preparation of Compound 7, except that 9-bromophenanthrene was used instead of 4-bromobiphenyl.
  • Compound 12 was prepared in the same manner as Compound 11, except that Compound A3 was used instead of Compound A2.
  • Compound 12 was prepared in the same manner as Compound 11, except that Compound B4 was used instead of Compound B3, and Compound A4 was used instead of Compound A2.
  • Compound 14 was prepared in the same manner as Compound 11, except that Compound B5 was used instead of Compound B3 and Compound A5 was used in place of Compound A2.
  • a glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 A was immersed in distilled water containing a dispersant and washed with ultrasonic waves.
  • the detergent was a product of Fischer Co.
  • the distilled water was supplied by Millipore Co. Distilled water, which was secondly filtered with a filter of the product, was used. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, isopropyl alcohol, acetone, methanol solvent Followed by ultrasonic cleaning in this order and drying.
  • the following HI1 compound was thermally vacuum deposited on the prepared ITO transparent electrode to a thickness of 500 A to form a hole injection layer.
  • the following compound (900A), which is a material for transporting holes, was vacuum deposited to form a hole transport layer.
  • the compound 2 prepared above was vacuum-deposited to a thickness of 50 A on the hole transport layer to form a hole control layer.
  • a host compound (BH1) and a dopant compound (BD1) 25: 1 weight ratio
  • the following ET1 compound (50A) was formed as an electron control layer and co-deposited with the following ET2 compound and the following LiQ compound (1: 1 weight ratio, 310A) to form an electron transport layer sequentially.
  • Lithium fluoride (LiF), Mg and Ag (10: 1, weight ratio, 150A) were sequentially deposited on the electron transporting layer and a cathode was formed by depositing aluminum having a thickness of 10 ⁇ and a thickness of ⁇ to prepare an organic light emitting device.
  • the deposition rate of the organic material was maintained at 1 A / sec, the lithium fluoride was maintained at 0.2 A / sec, and the aluminum was maintained at the deposition rate of 3 to 7 A / sec.
  • the vacuum degree was 1 ⁇ K ⁇ 7 to 5 ⁇ 10- 8 torr was maintained. Examples 2 to 22
  • An organic light emitting device was prepared in the same manner as in Example 1 except that the compound shown in the following Table 1 was used as a hole transporting layer and a hole controlling layer. Comparative Examples 1 to 7
  • An organic light emitting device was prepared in the same manner as in Example 1 except that the compound shown in the following Table 1 was used as a hole transporting layer and a hole controlling layer.
  • Table 1 the compounds of HT2, HT3, HT4, HT5, HT6, HT7 and HT8 are

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Abstract

La présente invention concerne un nouveau composé et un élément électroluminescent organique l'utilisant.
PCT/KR2018/007716 2017-10-24 2018-07-06 Nouveau composé et élément électroluminescent organique l'utilisant Ceased WO2019083122A1 (fr)

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Cited By (3)

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KR20210011301A (ko) * 2019-07-22 2021-02-01 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기발광 소자
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WO2021134820A1 (fr) * 2019-12-31 2021-07-08 南京高光半导体材料有限公司 Nouveau composé électroluminescent organique et dispositif électroluminescent organique

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