WO2020009442A1 - Nouveau composé et dispositif électroluminescent organique l'utilisant - Google Patents

Nouveau composé et dispositif électroluminescent organique l'utilisant Download PDF

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WO2020009442A1
WO2020009442A1 PCT/KR2019/008072 KR2019008072W WO2020009442A1 WO 2020009442 A1 WO2020009442 A1 WO 2020009442A1 KR 2019008072 W KR2019008072 W KR 2019008072W WO 2020009442 A1 WO2020009442 A1 WO 2020009442A1
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compound
group
substituted
unsubstituted
light emitting
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정민우
이동훈
장분재
이정하
한수진
박슬찬
황성현
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LG Chem Ltd
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LG Chem Ltd
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Priority claimed from KR1020190078377A external-priority patent/KR102278532B1/ko
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Priority to CN201980032000.0A priority Critical patent/CN112119081B/zh
Priority to US17/055,753 priority patent/US11787818B2/en
Publication of WO2020009442A1 publication Critical patent/WO2020009442A1/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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D411/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • organic light 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 material layer between the anode and the cathode.
  • the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • Patent Document 1 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by Formula 1:
  • X 1 to X 3 are each independently N or CH, at least two of X 1 to X 3 are N,
  • Y is O or 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 one or more heteroatoms selected from the group consisting of substituted or unsubstituted O, N, Si and S,
  • A is represented by the following formula (2) or (3),
  • Each Z is independently CR; Or two adjacent Z's are C linked with Formula 4 to form a fused ring, and the other two are each independently CR;
  • T is O, S, CQ 1 Q 2 , or NAr 4 ,
  • Ar 1 to Ar 4 are each independently, substituted or unsubstituted C 6-60 aryl; Or C 2-60 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
  • R and R 1 to R 8 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Substituted or unsubstituted C 1-60 haloalkyl; Substituted or unsubstituted C 1-60 alkoxy; Substituted or unsubstituted C 1-60 haloalkoxy; Substituted or unsubstituted C 3-60 cycloalkyl; Substituted or unsubstituted C 2-60 alkenyl; Substituted or unsubstituted C 6-60 aryl; Substituted or unsubstituted C 6-60 aryloxy; Or C 2-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, O and S,
  • Q 1 and Q 2 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted C 1-60 alkyl; Or substituted or unsubstituted C 6-60 aryl,
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the compound represented by Chemical Formula 1. .
  • 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.
  • FIG. 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, and an electron transport layer 8.
  • An example of the organic light emitting element consisting of the electron injection layer 9 and the cathode 4 is shown.
  • Means a bond connected to another substituent, and a single bond means a case where no separate atom is present in a portion represented by L 1 and L 2 .
  • substituted or unsubstituted is deuterium; Halogen group; Cyano group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; An alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heteroaryl including one or more of N, O and S atoms, or substituted or unsubstituted with two or more substituents selected from the group consisting of heteroary
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • 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. Specifically, 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 includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the present invention is not limited thereto.
  • the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, and the like.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, 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 linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • 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 an exemplary embodiment, 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 phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the fluorenyl group is substituted,
  • the heteroaryl is a heteroaryl containing one or more of O, N, Si, and S as heterologous elements, and the number of carbon atoms 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, triazole group, azo Credyl 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
  • the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above.
  • the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned 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 except that the arylene is a divalent group.
  • 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.
  • the present invention provides a compound represented by the formula (1).
  • X 1 to X 3 is N
  • X 1 and X 2 are N, X 3 is CH, or
  • X 1 and X 3 may be N, and X 2 may be CH.
  • L 1 and L 2 are each independently a single bond, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthrenylene, substituted Or unsubstituted anthracenylene, substituted or unsubstituted fluoranthhenylene, substituted or unsubstituted triphenylenylene, substituted or unsubstituted pyrenylene, substituted or unsubstituted carbazoylene, substituted or unsubstituted Fluorenylene, or substituted or unsubstituted spiro-fluorenylene.
  • L 1 and L 2 may each independently be a single bond, phenylene, or biphenylylene.
  • At least one of L 1 and L 2 may be a single bond.
  • Ar 1 and Ar 2 are each independently, substituted or unsubstituted C 6-20 aryl; Or C 2-20 heteroaryl including one hetero atom selected from the group consisting of substituted or unsubstituted O, N, and S.
  • Ar 1 and Ar 2 may each independently be phenyl, biphenylyl, terphenylyl, naphthyl, phenanthrenyl, dibenzothiophenyl, or carbazolyl.
  • Ar 1 and Ar 2 may both be phenyl.
  • A may be a structure of Chemical Formula 2 or 3, or Chemical Formula 2 or 3 may be a condensed structure with Chemical Formula 4, and such A may be specifically represented by Chemical Formulas 4a to 4n:
  • T is O, S, CQ 1 Q 2 , or NAr 4 ,
  • Ar 3 and Ar 4 are each independently C 6-20 aryl
  • Each R is, independently, hydrogen or C 6-20 aryl
  • Q 1 and Q 2 may each independently be hydrogen, C 1-10 alkyl, or C 6-20 aryl.
  • Ar 3 and Ar 4 are phenyl, each R is independently hydrogen or phenyl, and Q 1 and Q 2 may be methyl, but are not limited thereto. .
  • A may be any one selected from the structures represented by the following 5a to 5k:
  • R, Ar 3 and Ar 4 may each independently be C 6-20 aryl.
  • R, Ar 3 and Ar 4 may be phenyl, but is not limited thereto.
  • R 1 to R 8 may each independently be hydrogen, deuterium, halogen, cyano, nitro, amino, C 1-20 alkyl, or C 6-20 aryl. Specifically, all of R 1 to R 8 may be hydrogen, but are not limited thereto.
  • the compound may be represented by any one of the following Formulas 1-1 to 1-3:
  • the compound may be any one selected from the group consisting of the following compounds:
  • Step 1-1 is a step for preparing the intermediate compound I-1 by introducing a carbazole-based substituent on the starting material S-1
  • step 1-2 is introduced to the reactor for the Suzuki-coupling reaction intermediate compound I-2
  • Step 1-3 is a step of preparing a compound represented by the formula (1) by introducing a triazine-based substituent by the Suzuki-coupling reaction.
  • the Suzuki-coupling reaction is preferably carried out under a palladium catalyst and base, the reactor for the reaction can be changed to a reactor known in the art. This manufacturing method may be more specified in the production examples to be described later.
  • the compound represented by Formula 1 has a structure in which a triazine-based substituent and a carbazole-based substituent are simultaneously bonded to a benzopurodibenzothiophene or a benzothienodibenzothiophene core, and an organic light-emitting device employing the same is conventionally known as benzopurodibenzo Compared with the organic light emitting element employing a compound having a thiophene or a benzothienodibenzothiophene core, it can have high efficiency, low drive voltage, high brightness, long life and the like.
  • the present invention provides an organic light emitting device comprising the compound represented by the formula (1).
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the compound represented by Chemical Formula 1. .
  • 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 an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer may include a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the compound according to the present invention can be used as a host of the light emitting layer.
  • the compound according to the present invention can be used as a green phosphorescent host of the light emitting layer.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include two or more types of hosts, wherein one of the hosts may be a compound represented by Chemical Formula 1.
  • the organic material layer may include an electron transport layer, or an electron injection layer, the electron transport layer, or the electron injection layer may include a compound represented by the formula (1).
  • 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 further includes a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, an electron transport layer and an electron injection layer between the light emitting layer and the second electrode, in addition to the light emitting layer as an organic layer. It may have a structure to.
  • the structure of the organic light emitting device is not limited thereto, and may include fewer or more organic layers.
  • the organic light emitting device has a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate in which the first electrode is an anode and the second electrode is a cathode. It may be a light emitting device.
  • the organic light emitting device according to the present invention has an inverted type structure in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate, wherein the first electrode is a cathode and the second electrode is an anode. It may be an organic light emitting device.
  • FIGS. 1 and 2 the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer.
  • the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer.
  • the compound represented by Formula 1 may be included in the emission layer.
  • the organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
  • PVD physical vapor deposition
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then, a material that may be used as a cathode may be deposited thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Chemical Formula 1 may be formed as an organic material 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, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material (WO 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 usually 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 (ITO), indium zinc oxide (IZO); Combinations of metals and oxides 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, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer
  • the compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
  • the material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the electron blocking layer is formed on the hole transport layer, preferably provided in contact with the light emitting layer, to control the hole mobility, to prevent excessive movement of electrons to increase the hole-electron coupling efficiency of the organic light emitting device Means a layer that serves to improve.
  • the electronic blocking layer may include an electronic blocking material, and examples of the electronic blocking material may include an arylamine-based organic material, but are not limited thereto.
  • 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-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material as described above.
  • the host material may include a compound represented by Chemical Formula 1.
  • the emission layer may include two or more hosts, wherein one of the hosts is a compound represented by Chemical Formula 1, and as the other host material, a condensed aromatic ring derivative or a hetero ring-containing compound may be used.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the emission layer may include two types of hosts, and the two types of hosts may be compounds represented by Formula 1 and biscarbazole derivatives, respectively.
  • Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the arylamine, and one or two or more substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted.
  • substituents selected from the group consisting of aryl group, silyl group, alkyl group, cycloalkyl group and arylamino group are substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like but is not limited thereto.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material that can inject electrons well from the cathode and transfer them to the light emitting layer. Suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • 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, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
  • the electron injection layer is a layer for injecting electrons from an electrode, has an ability 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 the 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 the 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-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) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • 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.
  • the solid was dissolved in 700 mL of chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a pale green solid compound 1-1 (16.7 g, 68%).
  • compound 1-1 (16.7 g, 35.3 mmol), bis (pinacolato) diboron (9.9 g, 38.8 mmol) and potassium acetate (6.9 g, 70.6 mmol) were mixed and added to 200 ml of dioxane, Heated with stirring.
  • Bis (dibenzylideneacetone) palladium (0.6 g, 1.1 mmol) and tricyclohexylphosphine (.6 g, 2.2 mmol) were added under reflux, and the mixture was heated and stirred for 3 hours. After the reaction was completed, the temperature was lowered to room temperature, followed by filtration. Water was added to the filtrate, and the mixture was extracted with chloroform, and the organic layer was dried over anhydrous magnesium sulfate. Distillation under reduced pressure and recrystallization with ethanol to give compound 1-2 (15.2g, 76%).
  • compound 1-2 (15.2 g, 26.9 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (7.2 g, 26.9 mmol) were added to 200 ml of tetrahydrofuran and stirred. And reflux. Thereafter, potassium carbonate (11.2 g, 80.7 mmol) was dissolved in 30 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (0.9 g, 3 mol%) was added thereto. After 4 hours the reaction was lowered to room temperature and filtered. The filtrate was dissolved in chloroform and extracted with water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 1 (9.2 g, 51%) by ethyl acetate recrystallization.
  • the solid was dissolved in 700 mL of chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a pale green solid compound 6-1 (21.9 g, 75%).
  • compound 6-1 (21.9 g, 38.9 mmol), bis (pinacolato) diboron (10.9 g, 42.8 mmol) and potassium acetate (7.6 g, 77.8 mmol) were mixed and added to 200 ml of dioxane Heated with stirring.
  • bis (dibenzylideneacetone) palladium 7 g, 1.2 mmol
  • tricyclohexylphosphine 0.7 g, 2.4 mmol
  • compound 6-2 (20.6 g, 36.5 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (9.7 g, 36.5 mmol) were added to 200 ml of tetrahydrofuran and stirred. And reflux. Thereafter, potassium carbonate (15.1 g, 109.3 mmol) was dissolved in 30 ml of water, sufficiently stirred, and then tetrakistriphenyl-phosphinopalladium (1.3 g, 3 mol%) was added thereto. After 4 hours the reaction was lowered to room temperature and filtered. The filtrate was dissolved in chloroform and extracted with water, and then the organic layer was dried over magnesium sulfate. After drying the organic layer was prepared compound 6 (17.5 g, 63%) by ethyl acetate recrystallization.
  • the solid was dissolved in 700 mL of chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to obtain a pale green solid compound 7-1 (19.6 g, 69%).
  • compound 7-1 (19.6 g, 35.7 mmol), bis (pinacolato) diboron (10.0 g, 39.3 mmol) and potassium acetate (67.0 g, 71.4 mmol) were mixed and added to 200 ml of dioxane, Heated with stirring.
  • bis (dibenzylideneacetone) palladium (60.6 g, 1.01 mmol) and tricyclohexylphosphine (0.6 g, 2.2 mmol) were added thereto, and the mixture was heated and stirred for 3 hours. After the reaction was completed, the temperature was lowered to room temperature, followed by filtration.
  • the solid was dissolved in 700 mL of chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a pale pale green solid compound 8-1 (19.6 g, 69%).
  • the solid was dissolved in 700 mL of chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a pale green solid compound 9-1 (16.5 g, 58%).
  • compound 8-1 (16.5 g, 30.1 mmol), bis (pinacolato) diboron (8.4 g, 33.1 mmol) and potassium acetate (5.9 g, 60.1 mmol) were mixed and added to 200 ml of dioxane, Heated with stirring.
  • bis (dibenzylideneacetone) palladium 0.5 g, 0.9 mmol
  • tricyclohexylphosphine 0.5 g, 1.8 mmol
  • the solid was dissolved in 700 mL of chloroform, washed twice with water, and then the organic layer was separated, anhydrous magnesium sulfate was added thereto, stirred, and filtered. The filtrate was distilled under reduced pressure. The concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a pale pale green solid compound 10-1 (16.1 g, 66%).
  • compound 10-1 (16.1 g, 32.9 mmol), bis (pinacolato) diboron (9.2g, 36.2mmol) and potassium acetate (6.5 g, 65.8 mmol) were mixed and added to 200 ml of dioxane, Heated with stirring.
  • bis (dibenzylideneacetone) palladium (6 g, 1.0 mmol) and tricyclohexylphosphine (0.6 g, 2.0 mmol) were added thereto, and the mixture was heated and stirred for 3 hours. After the reaction was completed, the temperature was lowered to room temperature, followed by filtration.
  • the glass substrate coated with ITO (indium tin oxide) having a thickness of 1,300 kPa was put in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. was used as a detergent
  • distilled water was filtered secondly as a filter of Millipore Co. as a distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the hole injection layer was formed by thermally vacuum depositing the following HI-1 compound to a thickness of 50 kPa on the prepared ITO transparent electrode.
  • a hole transport layer was formed by thermal vacuum deposition of the following HT-1 compound to a thickness of 250 GPa on the hole injection layer, and an electron blocking layer was formed by vacuum deposition of the following HT-2 compound to 50 GPa on the HT-1 deposition film.
  • Compound 1 the following YGH-1 compound, and phosphorescent dopant YGD-1, which were prepared in Preparation Example 1 as a light emitting layer on the HT-2 deposited film, were co-deposited at a weight ratio of 44:44:12 to form a light emitting layer having a thickness of 400 kHz.
  • ET-1 compound was vacuum deposited to a thickness of 250 kPa on the light emitting layer to form an electron transport layer
  • the following ET-2 compound and Li were vacuum deposited on the electron transport layer at a weight ratio of 98: 2 to form an electron injection layer having a thickness of 100 kW. Formed.
  • Aluminum was deposited on the electron injection layer to a thickness of 1000 ⁇ to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ / sec
  • the aluminum was maintained at the deposition rate of 2 ⁇ / sec
  • the vacuum during deposition was maintained at 1 ⁇ 10 -7 ⁇ 5 ⁇ 10 -8 torr It was.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of the compound 1 of Preparation Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of the compound 1 of Preparation Example 1.
  • the structures of the compounds of CE1, CE2, CE3 and CE4 used in Table 1 are as follows.
  • the lifetime LT 95 means a time taken for the luminance to decrease to 95% of the initial luminance.
  • the organic light emitting device using the compound of the present invention as the host material of the light emitting layer compared with the organic light emitting device using the comparative material as the host material of the light emitting layer, the efficiency is equivalent to the level of significantly improved life characteristics It can be seen that.
  • a compound having a structure in which a triazine-based substituent and a carbazole-based substituent are simultaneously bonded to a benzopurodibenzothiophene or a benzothienodibenzothiophene core represented by Formula 1 only one of these substituents is bonded. It seems to be due to the increased charge stability compared to the compound of.
  • substrate 2 anode

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

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique l'utilisant.
PCT/KR2019/008072 2018-07-03 2019-07-02 Nouveau composé et dispositif électroluminescent organique l'utilisant Ceased WO2020009442A1 (fr)

Priority Applications (2)

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CN201980032000.0A CN112119081B (zh) 2018-07-03 2019-07-02 新的化合物和包含其的有机发光器件
US17/055,753 US11787818B2 (en) 2018-07-03 2019-07-02 Compound and organic light emitting device comprising the same

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KR20180077237 2018-07-03
KR10-2018-0077237 2018-07-03
KR10-2019-0078377 2019-06-28
KR1020190078377A KR102278532B1 (ko) 2018-07-03 2019-06-28 신규한 화합물 및 이를 이용한 유기발광 소자

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WO2022230574A1 (fr) * 2021-04-26 2022-11-03 株式会社Kyulux Matériau de transport de charge, composition et élément luminescent organique
CN115298843A (zh) * 2020-06-26 2022-11-04 株式会社Lg化学 有机发光器件
JP2022168813A (ja) * 2021-04-26 2022-11-08 株式会社Kyulux 電荷輸送材料、組成物および有機発光素子

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KR101340241B1 (ko) * 2008-06-05 2013-12-10 이데미쓰 고산 가부시키가이샤 다환계 화합물 및 그것을 이용한 유기 전기발광 소자
KR20170086329A (ko) * 2016-01-18 2017-07-26 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자
KR20170086243A (ko) * 2016-01-18 2017-07-26 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자
KR20170086277A (ko) * 2016-01-18 2017-07-26 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자

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KR101340241B1 (ko) * 2008-06-05 2013-12-10 이데미쓰 고산 가부시키가이샤 다환계 화합물 및 그것을 이용한 유기 전기발광 소자
KR20170086329A (ko) * 2016-01-18 2017-07-26 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자
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KR20170086277A (ko) * 2016-01-18 2017-07-26 에스에프씨 주식회사 유기발광 화합물 및 이를 포함하는 유기발광소자

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115298843A (zh) * 2020-06-26 2022-11-04 株式会社Lg化学 有机发光器件
WO2022230574A1 (fr) * 2021-04-26 2022-11-03 株式会社Kyulux Matériau de transport de charge, composition et élément luminescent organique
JP2022168813A (ja) * 2021-04-26 2022-11-08 株式会社Kyulux 電荷輸送材料、組成物および有機発光素子
JP7764013B2 (ja) 2021-04-26 2025-11-05 株式会社Kyulux 電荷輸送材料、組成物および有機発光素子

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