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WO2020111613A1 - Nouveau composé et diode électroluminescente organique le comprenant - Google Patents

Nouveau composé et diode électroluminescente organique le comprenant Download PDF

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WO2020111613A1
WO2020111613A1 PCT/KR2019/015685 KR2019015685W WO2020111613A1 WO 2020111613 A1 WO2020111613 A1 WO 2020111613A1 KR 2019015685 W KR2019015685 W KR 2019015685W WO 2020111613 A1 WO2020111613 A1 WO 2020111613A1
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group
layer
compound
substituted
light emitting
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Korean (ko)
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정민우
이동훈
장분재
홍완표
서상덕
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 KR1020190145978A external-priority patent/KR102352825B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to US17/278,406 priority Critical patent/US12098156B2/en
Priority to CN201980060834.2A priority patent/CN112714763A/zh
Publication of WO2020111613A1 publication Critical patent/WO2020111613A1/fr
Anticipated expiration legal-status Critical
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K77/00—Constructional details of devices covered by this subclass and not covered by groups H10K10/80, H10K30/80, H10K50/80 or H10K59/80
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Definitions

  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • 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 relates to a novel organic light emitting material and an organic light emitting device comprising the same.
  • X 1 to X 6 are each independently CH or N, provided that at least one of X 1 to X 6 is N,
  • Ar 1 to Ar 4 are each independently, substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S, provided that at least one of Ar 1 to Ar 4 is selected from the group consisting of: Which one;
  • R 3 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
  • a is an integer from 0 to 8
  • R 1 is hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-60 aryl; Or a substituted or unsubstituted C 2-60 heteroaryl including any one or more selected from the group consisting of N, O and S,
  • n is an integer from 0 to 8.
  • 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 at least one layer of the organic material layer includes a compound represented by Chemical Formula 1, and provides an organic light emitting device. .
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • Figure 2 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), light emitting layer (3), hole blocking layer (7), electron transport layer (8), electron injection layer (9) And an example of an organic light-emitting device comprising the cathode 4.
  • FIG. 3 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (10), light emitting layer (3), hole blocking layer (7), electron transport layer (8) ,
  • An example of an organic light-emitting device consisting of an electron injection layer 9 and a cathode 4 is shown.
  • the present invention provides a compound represented by Formula 1 above.
  • substituted or unsubstituted refers to 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; Ar 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
  • 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 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-butyl dimethyl 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.
  • 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 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 monocyclic aryl group, such as a phenyl group, a biphenyl group, a terphenyl 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 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, triazole group, Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group,
  • 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 described above.
  • the alkyl group among the aralkyl group, alkylaryl group, and alkylamine group is the same as the above-described example of the alkyl group.
  • heteroarylamine among heteroarylamines may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group in the alkenyl group 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 the 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.
  • X 1 to X 6 are each independently CH or N, provided that at least one of X 1 to X 3 is N, and at least one of X 4 to X 6 is N.
  • X 1 to X 6 may each be N.
  • Ar 1 to Ar 4 are each independently, substituted or unsubstituted C 6-20 aryl; Or C 2-20 heteroaryl including any one or more selected from the group consisting of substituted or unsubstituted N, O and S, provided that at least one of Ar 1 to Ar 4 is selected from the group consisting of: Can be any one;
  • R 2 is hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-20 aryl; Or C 2-20 heteroaryl containing any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
  • R 3 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-20 aryl; Or C 2-20 heteroaryl containing any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
  • a is an integer from 0 to 8.
  • R 2 and R 3 may each independently be hydrogen, deuterium, phenyl, or phenyl substituted with 5 deuterium.
  • Ar 1 to Ar 4 are each independently phenyl, biphenylyl, naphthyl, phenanthrenyl, triphenylenyl, dibenzofuranyl, dibenzothiophenyl, dimethylfluorenyl, carbazolyl, Phenyl carbazolyl, phenyl substituted with 5 deuterium, carbazolyl substituted with phenyl substituted with 5 deuterium, or
  • at least one of Ar 1 to Ar 4 may be any one selected from the group consisting of:
  • R 1 is hydrogen; heavy hydrogen; Substituted or unsubstituted C 6-20 aryl; Or C 2-20 heteroaryl containing any one or more selected from the group consisting of substituted or unsubstituted N, O and S,
  • R 1 may be hydrogen, phenyl, or phenyl substituted with 1 to 5 deuterium.
  • n can be 0 or 1.
  • the compound represented by the formula (1) for example, can be prepared by the same method as in Scheme 1, and other compounds can be similarly prepared.
  • X 1 to X 6 , Ar 1 to Ar 4 , R 1 and n are as defined in Chemical Formula 1, and Z 1 and Z 2 are each independently halogen, preferably Z 1 and Z 2 are each independently chloro or fluoro.
  • the first reaction of Reaction Scheme 1 is a Suzuki coupling reaction, and is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be modified as known in the art.
  • the second reaction of Reaction Scheme 1 is an amine substitution reaction, and is preferably performed in the presence of a palladium catalyst and a base, and the reactor for the amine substitution reaction can be changed as known in the art.
  • the manufacturing method may be more specific in the manufacturing examples to be described later.
  • 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 an organic light emitting device including at least one layer of an organic material provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes a compound represented by Chemical Formula 1, and an organic light emitting device is provided. 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 multi-layer 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, a light emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer 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 material layers.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1.
  • the organic material layer may include a hole transport layer, a hole injection layer, or a layer simultaneously performing hole transport and hole injection
  • the hole transport layer, a hole injection layer, or a layer simultaneously performing hole transport and hole injection may have the formula It may contain a compound represented by 1.
  • the electron transport layer, the electron injection layer, or a layer that simultaneously performs electron transport and electron injection may include a compound represented by Chemical Formula 1.
  • the organic light emitting device according to the present invention may be an organic light emitting device having a structure (normal type) in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. Further, the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of the 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 device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • the compound represented by Chemical Formula 1 may be included in the light emitting layer.
  • Figure 2 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), light emitting layer (3), hole blocking layer (7), electron transport layer (8), electron injection layer (9) And an example of an organic light-emitting device comprising the cathode 4.
  • the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the light emitting layer, the blocking layer, the electron transport layer and the electron injection layer.
  • FIG. 3 is a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (10), light emitting layer (3), hole blocking layer (7), electron transport layer (8) ,
  • An example of an organic light-emitting device consisting of an electron injection layer 9 and a cathode 4 is shown.
  • the compound represented by Chemical Formula 1 may be included in one or more of the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the blocking layer, the electron transport layer, and the electron injection layer.
  • the organic light-emitting device according to the present invention can be made of materials and methods known in the art, except that at least one layer of the organic material layer contains 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 can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a positive electrode is formed by depositing metal or conductive metal oxides or alloys 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 injection layer, 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 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 when manufacturing an organic light emitting device.
  • 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 first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • 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 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;
  • a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the hole injection layer is a layer for injecting holes from an electrode, and has the ability to transport holes as a hole injection material, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in the light emitting layer.
  • a compound that prevents migration of the excitons to the electron injection layer or the electron injection material and has excellent thin film formation ability is preferred.
  • the high 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 layer.
  • 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.
  • Organic anthraquinone and polyaniline and polythiophene-based conductive polymers are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes from the hole injection layer to the light emitting layer. It is a material that transports holes from the anode or the hole injection layer as a hole transport material and transfers them to the light emitting layer. This is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • the electron blocking layer is a layer between the hole transport layer and the light emitting layer to prevent electrons injected from the cathode from being recombined in the light emitting layer and passing over the hole transport layer, and is also referred to as an electron blocking layer.
  • the electron blocking layer is preferably a material having a smaller electron affinity than the electron transport layer.
  • a material capable of emitting light in the visible region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively is preferably a material having good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.
  • 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.
  • examples of the metal complex include an iridium complex, a platinum complex, and the like, but are not limited thereto.
  • the electron injection layer is a layer that injects electrons from an electrode, has the ability to transport electrons, has an electron injection effect from a cathode, an excellent electron injection effect for a light emitting layer or a light emitting material, and injects holes generated in the light emitting layer A compound that prevents migration to the layer and has excellent thin film forming ability is preferred.
  • 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.
  • the compound A1 (14.0 g, 30 mmol), bis (pinacolato) diboron (8.5 g, 33 mmol) and potassium acetate (5.9 g, 61 mmol) are mixed, added to 210 ml of dioxane and stirred. While heating. In reflux, bis(dibenzylidineacetone)palladium (0.52 g, 0.9 mmol) and tricyclohexylphosphine (0.51 g, 1.8 mmol) were added and heated and stirred for 6 hours. After the reaction was completed, the temperature was reduced to room temperature and filtered.
  • Triazine is 2-chloro-4-(dibenzothiophen-4-yl)-6-phenyl-1,3,5 instead of 2-chloro-4,6-diphenyl-1,3,5-triazine -Compound 6 was prepared by the same method as Production Example 1, except that triazine was used.
  • 2-chloro-4,6-diphenyl-1,3,5-triazine (50.0 g, 19 mmol) and (3-chloro-4-fluorophenyl)boronic acid (32.6 g, 19 mmol) are tetrahydro Dissolved in 1000 mL of furan. After adding a potassium carbonate 2M solution (200 mL), tetrakis-(triphenylphosphine)palladium (2.2 g, 1.9 mmol) was added and refluxed for 2 hours.
  • ITO Indium Tin Oxide
  • distilled water filtered secondarily by a filter of Millipore Co.
  • ultrasonic washing was repeated for 2 minutes with distilled water twice.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and then transported to a plasma cleaner.
  • the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.
  • the following compound HI-A was thermally vacuum-deposited to a thickness of 100 ⁇ on the prepared ITO transparent electrode to form a hole injection layer. Subsequently, only the compound HT-A was thermally vacuum-deposited to a thickness of 800 ,, and the compound HT-B was subsequently vacuum-deposited to a thickness of 500 ⁇ to form a hole transport layer. Subsequently, as the first host of the light emitting layer, Compound 1 and the second host prepared in Preparation Example 1 were vacuum-deposited at a weight ratio of 50:50 and 6% by weight of the compound GD of the two host weights at a thickness of 350 MPa. .
  • the following ET-A was vacuum-deposited to a thickness of 50 MPa as a hole blocking layer.
  • the following ET-B and Liq as the electron transport and injection layer were thermally vacuum-deposited to a thickness of 250 MPa at a weight ratio of 1:1, and then LiF was vacuum-deposited to a thickness of 30 MPa.
  • the electron injection layer was deposited to a thickness of 1000 ⁇ to form a cathode, thereby manufacturing an organic light emitting device.
  • the organic light emitting devices of Examples 2 to 11 were manufactured in the same manner as in Example 1, except that the compound shown in Table 1 below was used instead of Compound 1 as a host material.
  • the organic light emitting device manufactured by using the compound according to the present invention as a host of the light emitting layer exhibits excellent performance in terms of voltage, efficiency, and lifetime compared to the organic light emitting device of Comparative Example. .
  • This is presumed to be because when an aryl or heteroaryl condensed ring substituent is substituted on a nitrogen-containing heterocyclic group such as triazine, it is advantageous for electron and hole transport and molecular stability can be enhanced.
  • Example 1 and Comparative Example 2 it was confirmed that the difference in voltage and life was observed depending on the presence or absence of a phenylene linker between carbazole and triazine.
  • substrate 2 anode

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  • Plural Heterocyclic Compounds (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé et une diode électroluminescente organique l'utilisant.
PCT/KR2019/015685 2018-11-27 2019-11-15 Nouveau composé et diode électroluminescente organique le comprenant Ceased WO2020111613A1 (fr)

Priority Applications (2)

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US17/278,406 US12098156B2 (en) 2018-11-27 2019-11-15 Compound and organic light emitting device comprising the same
CN201980060834.2A CN112714763A (zh) 2018-11-27 2019-11-15 新的化合物和包含其的有机发光器件

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KR20160041768A (ko) * 2014-10-08 2016-04-18 주식회사 알파켐 신규한 발광용 호스트 물질 및 이를 이용한 유기 발광 소자
KR20160066339A (ko) * 2014-12-02 2016-06-10 주식회사 두산 유기 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20170049291A (ko) * 2015-10-28 2017-05-10 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
CN107954922A (zh) * 2017-11-28 2018-04-24 上海道亦化工科技有限公司 一种联苯基二咔唑衍生物及其用途和有机电致发光器件

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KR20100131939A (ko) * 2009-06-08 2010-12-16 에스에프씨 주식회사 인돌로카바졸 유도체 및 이를 이용한 유기전계발광소자
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