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WO2019182360A1 - Composé, dispositif électroluminescent organique et dispositif d'affichage - Google Patents

Composé, dispositif électroluminescent organique et dispositif d'affichage Download PDF

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WO2019182360A1
WO2019182360A1 PCT/KR2019/003261 KR2019003261W WO2019182360A1 WO 2019182360 A1 WO2019182360 A1 WO 2019182360A1 KR 2019003261 W KR2019003261 W KR 2019003261W WO 2019182360 A1 WO2019182360 A1 WO 2019182360A1
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water
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김정미
이종호
박기선
김미정
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SK Materials Co Ltd
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SK Materials Co Ltd
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Priority to KR1020197025269A priority patent/KR102084906B1/ko
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic 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
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic 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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/06—Peri-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
    • C07D495/06—Peri-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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers

Definitions

  • the present invention relates to a compound, an organic light emitting element, and an organic EL display device.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often formed 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 and an electron injection layer.
  • organic monomolecular substances include PBD (2-biphenyl-4-yl-5- (4-t-butylphenyl) -1,3,4-oxadiazole) derivatives bound to Spiro compounds and TPBI (2, 2 ', 2 "-(benzene-1,3,5-triyl) -tris (1-phenyl-1H-benzimidazole) and the like are known.
  • An object of the present invention is to provide an organic light emitting device having a high efficiency and a low driving voltage and a display device using the same through a compound having high electron mobility and excellent hole blocking ability.
  • a 1 is a group represented by any one of the following structures
  • Y1 is any one of S, O, or C
  • X 4 to X 9 are the same as or different from each other, and each independently N or C,
  • Ar 5 and Ar 6 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, A substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted C 1 -C 60 heteroaryl group,
  • L is a direct bond; Substituted or unsubstituted arylene group; Substituted or unsubstituted hetero arylene group; Or a substituted or unsubstituted C 9 ⁇ C 60 condensed polycyclic group,
  • a 2 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or un
  • the compounds of the present invention have high electron mobility and are excellent in hole blocking ability.
  • the organic light emitting device using the compound of the present invention as an organic layer has high efficiency and low driving voltage.
  • FIG. 1 is an exemplary view of an organic light emitting device according to an embodiment of the present invention.
  • halo or halogen as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.
  • alkyl or “alkyl group” has a single bond of 1 to 60 carbon atoms, unless otherwise specified, and is a straight chain alkyl group, a branched chain alkyl group, a cycloalkyl (alicyclic) group, or an alkyl-substituted group.
  • radicals of saturated aliphatic functional groups including cycloalkyl groups, cycloalkyl-substituted alkyl groups.
  • 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
  • heteroalkyl group means that at least one of the carbon atoms constituting the alkyl group has been replaced with a heteroatom.
  • alkenyl group or “alkynyl group”, unless stated otherwise, has a double or triple bond of 2 to 60 carbon atoms, and includes a straight or branched chain group, and is not limited thereto. It is not.
  • 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.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto. Specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3, 4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.
  • alkoxyl group means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.
  • alkenoxyl group means an alkenyl group to which an oxygen radical is attached, and unless otherwise stated, it is 2 to 60 It has carbon number of, It is not limited to this.
  • aryloxyl group or “aryloxy group” means an aryl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 6 to 60, but is not limited thereto.
  • aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
  • an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
  • the aryl group may include, but is not limited to, a single ring aryl group, a phenyl group, a biphenyl group, a terphenyl group, and as a multicyclic aryl group, a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, It may include, but is not limited to, a chrysenyl group, a fluorenyl group, and a spirofluorene group.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the fluorenyl group When the fluorenyl group is substituted, it may have a structure as follows, but is not limited thereto.
  • aryl or "ar” means a radical substituted with an aryl group.
  • an arylalkyl group is an alkyl group substituted with an aryl group
  • an arylalkenyl group is an alkenyl group substituted with an aryl group
  • the radical substituted with an aryl group has the carbon number described herein.
  • an arylalkoxy group means an alkoxy group substituted with an aryl group
  • an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group
  • an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group.
  • the arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • heteroaryl group or “heteroarylene group” means an aryl group or arylene group having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. It may include at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.
  • heterocyclic group includes one or more heteroatoms, unless otherwise indicated, and has from 2 to 60 carbon atoms, and includes at least one of single and multiple rings, heteroaliphatic rings and hetero Aromatic rings are included. Adjacent functional groups may be formed in combination.
  • Heteroatom refers to N, O, S, P or Si unless otherwise stated.
  • Heterocyclic groups may also include rings comprising SO 2 in place of the carbon forming the ring.
  • heterocyclic group examples 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, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phen
  • aliphatic as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms
  • aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
  • ring refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a hetero ring having 2 to 60 carbon atoms, or a combination thereof. Saturated or unsaturated rings.
  • heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
  • carbonyl used in the present invention is represented by -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. Cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
  • ether as used herein is represented by -RO-R ', wherein R or R' are each independently of each other hydrogen, an alkyl group having 1 to 20 carbon atoms, It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.
  • substituted in the term “substituted or unsubstituted” as used herein refers to deuterium, halogen, amino, nitrile, nitro, C 1 -C 20 alkyl, C 1 -C 20 alkoxyl group, C 1 ⁇ C 20 alkylamine group, C 1 ⁇ C 20 alkylthiophene group, C 6 ⁇ C 20 arylthiophene group, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 alkynyl, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted by deuterium aryl group, a C 8 ⁇ C 20 aryl alkenyl group, a silane group, a boron Group, germanium group, and C 2 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consisting of,
  • the substituent R 1 when a is an integer of 0, the substituent R 1 is absent, when a is an integer of 1, one substituent R 1 is bonded to any one of carbons forming the benzene ring, and a is an integer of 2 or 3 are each bonded as follows, where R 1 may be the same or different from each other, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bonded to the carbon forming the benzene ring Is omitted.
  • FIG. 1 is an exemplary view of an organic light emitting device according to an embodiment of the present invention.
  • the organic light emitting diode 100 includes the first electrode 120, the second electrode 180, the first electrode 110, and the second electrode 180 formed on the substrate 110.
  • the organic material layer formed between the), the organic material layer comprises a compound according to the invention.
  • the first electrode 120 may be an anode (anode)
  • the second electrode 180 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • anode material a material having a large work function is preferable to facilitate the injection of holes into the organic material layer.
  • anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SNO 2 : Combination of metals and oxides such as 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 preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • the anode 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 organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. In this case, at least some of the remaining layers except for the emission layer 150 may not be formed.
  • the layers formed between the first electrode 120 and the light emitting layer 150 constitute a hole transport region
  • the layers formed on the second electrode 180 and the light emitting layer 150 constitute an electron transport region.
  • the hole injection layer 130 is a layer that facilitates the injection of holes from the first electrode 120, and the hole injection material is preferably a compound having excellent hole injection effect from the anode and thin film formation ability.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode 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 substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer 140 is a layer that receives holes from the hole injection layer 130 and transports holes to the light emitting layer 150.
  • a material having high mobility to holes 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 light emitting layer 150 emits light in the visible region by transporting and combining holes and electrons from the hole transport layer 140 and the electron transport layer 160, respectively, and the light emitting material has good quantum efficiency with respect to fluorescence or phosphorescence.
  • the substance is preferred. Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the light emitting layer 150 may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
  • 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.
  • Dopant materials include aromatic amine derivatives, strylamine 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 substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the electron transport layer 160 is a layer that receives electrons from the electron injection layer 170 and transports electrons to the emission layer 150, and a material having high mobility to electrons is suitable as the electron transport material. 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 material of the present invention will be described later.
  • the electron injection layer 170 is a layer that facilitates the injection of electrons from the second electrode 180, a compound having the ability to transport electrons and excellent in the electron injection effect and the thin film formation ability from the cathode electrode Do. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese and tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] qui Nolinato) 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-naphtholato) gallium, and the like It is not limited.
  • the organic material layer is a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, a buffer layer in addition to the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the electron transport layer 160, the electron injection layer 170. 141 may be further included, and the electron transport layer 160 may serve as a hole blocking layer.
  • the organic light emitting diode according to the present invention may include a protective layer or a light efficiency improving layer formed on one surface of the first electrode 120 and the second electrode 180 opposite to the organic material layer. It may further include.
  • the compound according to the present invention is used in an electron transport region such as an electron injection layer 170, an electron transport layer 160, a hole blocking layer, etc.
  • an electron transport region such as an electron injection layer 170, an electron transport layer 160, a hole blocking layer, etc.
  • the present invention is not limited thereto. It may also be used as a material for the hole transport region such as the layer 130, the hole transport layer 140, the host or the dopant of the light emitting layer 150, or the light efficiency improving layer.
  • the organic electroluminescent device may be manufactured using a physical vapor deposition (PVD) method such as vacuum evaporation or sputtering.
  • PVD physical vapor deposition
  • the anode 120 is formed by depositing a metal or conductive metal oxide or an alloy thereof on a substrate, and thereon, a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, and an electron transport layer ( After forming the organic layer including the 160 and the electron injection layer 170, it can be prepared by depositing a material that can be used as the cathode 180 thereon.
  • the organic material layer is a solution or solvent process (e.g., spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading) using various polymer materials. It can be produced in fewer layers by methods such as ding process, screen printing process, or thermal transfer method. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.
  • 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.
  • WOLED White Organic Light Emitting Device
  • Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented.
  • a side-by-side method in which R (Red), g (Green), and B (Blue) light emitting parts are mutually planarized, and a stacking method in which R, g, and B light emitting layers are stacked up and down.
  • a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light therefrom. May also be applied to these WOLEDs.
  • CCM color conversion material
  • Another embodiment of the present invention may include a display device including the organic light-emitting device of the present invention described above, and an electronic device including a control unit for controlling the display device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • a 1 is a group represented by any one of the following structures
  • Y1 is any one of S, O, or C
  • X 4 to X 9 are the same as or different from each other, and each independently N or C,
  • Ar 5 and Ar 6 are the same as or different from each other, and each independently hydrogen, deuterium, a halogen group, a cyano group, a substituted or unsubstituted C 1 to C 60 alkyl group, a substituted or unsubstituted C 3 to C 10 cycloalkyl group, A substituted or unsubstituted C 6 -C 60 aryl group, or a substituted or unsubstituted C 1 -C 60 heteroaryl group,
  • L is a direct bond; Substituted or unsubstituted arylene group; Substituted or unsubstituted hetero arylene group; Or a substituted or unsubstituted C 9 ⁇ C 60 condensed polycyclic group,
  • a 2 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted alkylamine group; A substituted or unsubstituted aralkylamine group; Substituted or un
  • L has the following structure, L1 ⁇ L3 are each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group; Or a substituted or unsubstituted C 9 to C 60 condensed polycyclic group.
  • L is a direct bond, a substituted or unsubstituted C 9 ⁇ C 60 condensed polycyclic group, or a group having the following structure.
  • l, m, and n are each independently 0 or 1.
  • a 2 is any one selected from the following structures.
  • X 1 to X 3 are each independently C or N, at least one of X 1 to X 3 is N, and Ar 1 and Ar 2 are each independently hydrogen, deuterium, halogen, cyano, substituted or Unsubstituted C 1 to C 60 alkyl group, substituted or unsubstituted C 3 to C 10 cycloalkyl group, substituted or unsubstituted C 6 to C 60 aryl group, or substituted or unsubstituted C 1 to C 60 heteroaryl group to be.
  • a 2 is represented by the following structural formula
  • X1 to X3 are each independently C or N, at least one of X1 to X3 is N, Ar1 and Ar2 are the same as or different from each other, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1
  • Ar3 is hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted C1-C60 alkyl group, substituted or unsubstituted C3-C10 cycloalkyl group, substituted or unsubstituted C6-C60 aryl group, or substituted
  • A2 is any one of the following groups.
  • the compound of Formula 1 is any one of the following compounds.
  • the first electrode A second electrode opposite the first electrode; And an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises the compound of Formula 1 described above.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the organic layer is i) a light emitting layer, ii) a hole injection layer interposed between the first electrode and the light emitting layer.
  • a hole transport region including at least one of a hole transport layer and an electron blocking layer
  • the electron transport region includes the compound of Formula 1.
  • the electron transport layer includes the compound of formula (1).
  • a display device including the organic light emitting element, wherein the first electrode of the organic light emitting element is electrically connected to a source electrode or a drain electrode of the thin film transistor.
  • 10-bromothiochromeno [4,3,2-ij] isoquinoline (1 equiv) was dissolved in DMF in a round bottom flask, followed by bis (pinacolato) diboron (1.1 equiv), Pd (dppf) Cl 2 (0.03 equiv), KOAc ( 3 equivalents) was added and refluxed at 130 ° C. for 4 hours. Upon completion of the reaction, DMF was removed by distillation and extracted with CH 2 Cl 2 and water.
  • 6-bromothiochromeno [4,3,2-de] quinazoline (1 equiv) was dissolved in DMF in a round bottom flask, followed by bis (pinacolato) diboron (1.1 equiv), Pd (dppf) Cl 2 (0.03 equiv), KOAc ( 3 equivalents) was added and refluxed at 130 ° C. for 4 hours. Upon completion of the reaction, DMF was removed by distillation and extracted with CH 2 Cl 2 and water.
  • Compound 1-1-2 to 1-1-3 can be synthesized in the same manner as Compound 1-1-1, using cores 1-2 to 1-3.
  • Compound 1-3-8 to 1-3-9 are Using cores 1-2 to 1-3, synthesis is possible in the same manner as for compounds 1-3-7.
  • Compound 1-3-11 to 1-3-12 are Using cores 1-2 to 1-3, synthesis is possible in the same manner as for compounds 1-3-10.
  • Compounds 2-1-2 to 2-1-10 can be synthesized in the same manner as for compounds 2-1-1, using cores 2-2 to 2-10.
  • Compounds 2-2-2 to 2-2-10 can be synthesized in the same manner as for compounds 2-2-1, using cores 2-2 to 2-10.
  • Compounds 2-2-12 to 2-2-20 can be synthesized in the same manner as for compounds 2-2-11, using cores 2-2 to 2-10.
  • Compounds 2-3-2 to 2-3-10 can be synthesized in the same manner as Compound 2-3-1, using cores 2-2 to 2-10.
  • Compounds 2-3-12 to 2-3-20 can be synthesized in the same manner as Compound 2-3-11, using Cores 2-2 to 2-10.
  • Compound 2-3-22 to 2-3-30 can be synthesize
  • Compounds 2-3-32 to 2-3-40 can be synthesized in the same manner as Compound 2-3-31, using cores 2-2 to 2-10.
  • Compounds 2-4-2 to 2-4-10 can be synthesized in the same manner as for compounds 2-4-1, using cores 2-2 to 2-10.
  • Compounds 2-4-12 to 2-4-20 can be synthesized in the same manner as for compounds 2-4-11, using cores 2-2 to 2-10.
  • Compounds 2-4-22 to 2-4-20 can be synthesized in the same manner as for compounds 2-4-21, using cores 2-2 to 2-10.
  • Compounds 2-4-32 to 2-4-40 can be synthesized in the same manner as for compounds 2-4-31, using cores 2-2 to 2-10.
  • Compounds 2-4-42 to 2-4-50 can be synthesized in the same manner as for compounds 2-4-41, using cores 2-2 to 2-10.
  • Compounds 2-4-52 to 2-4-60 can be synthesized in the same manner as for compounds 2-4-51, using cores 2-2 to 2-10.
  • Compounds 2-4-62 to 2-4-70 can be synthesized in the same manner as for compounds 2-4-61, using cores 2-2 to 2-10.
  • Compounds 2-4-72 to 2-4-80 can be synthesized in the same manner as for compounds 2-4-71, using cores 2-2 to 2-10.
  • Compound 4-1-2 can be synthesized in the same manner as Compound 4-1-1 using Core 4-2.
  • the remaining compounds 4-2-1 to 4-4-16 are the same as those in the corresponding synthesis examples in the synthesis examples of the compounds 2-1-1 to 2-4-80, using the core 4-1 or 4-2. Can be synthesized.
  • Compound 5-1-2 can be synthesized in the same manner as Compound 5-1-1 using Core 5-2.
  • the remaining compounds 5-2-1 to 5-4-16 are the same as those in the corresponding synthesis examples in the synthesis examples of the compounds 2-1-1 to 2-4-80, using the core 5-1 or 5-2 Can be synthesized.
  • the intermediate product 1- (3-bromophenyl) thiochromeno [4,3,2-ij] isoquinoline (15 g, 38.4 mmol) was dissolved in DMF in a round bottom flask, followed by 4,4,4 ', 4', 5,5, 5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxaborolane) (10.7 g, 42.3 mmol), Pd (dppf) Cl 2 (0.8 g, 1.2 mmol), KOAc (15.9 g, 115.3 mmol) was added and refluxed at 130 ° C. for 4 hours. Upon completion of the reaction, DMF was removed by distillation and extracted with CH 2 Cl 2 and water.
  • the remaining compounds can be synthesized in the same manner.
  • Example 1-38 Of the blue organic light emitting device To the electron transport layer Application example )
  • 2-TNATA was vacuum deposited on the ITO anode layer to form a hole injection layer having a thickness of 60 nm, and a 4,4'-bis [N- (1-naphthyl) -N-phenylamino] ratio was formed on the hole injection layer.
  • Phenyl hereinafter referred to as NPB was vacuum deposited to form a hole transport layer having a thickness of 30 nm.
  • LiF is vacuum deposited on the electron transport layer to form an electron injection layer having a thickness of 1nm, and the electron injection
  • An organic light-emitting device was manufactured by vacuum evaporating Al on the layer to form a 300 nm thick cathode.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example except for using the following ET1 instead of the compound represented by Formula 1 of the present invention as an electron transport layer material.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example except for using the following ET2 instead of the compound represented by Formula 1 of the present invention as an electron transport layer material.
  • the compound of the present invention can be used in an organic light emitting device and an organic EL display device including the same.

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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)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé qui peut être appliqué à une couche de transport d'électrons d'un dispositif électroluminescent organique, un dispositif électroluminescent organique utilisant ce composé et un dispositif d'affichage électroluminescent comprenant ce dispositif électroluminescent organique.
PCT/KR2019/003261 2018-03-23 2019-03-20 Composé, dispositif électroluminescent organique et dispositif d'affichage Ceased WO2019182360A1 (fr)

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WO2023223855A1 (fr) * 2022-05-20 2023-11-23 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique

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KR20240045767A (ko) 2022-09-30 2024-04-08 에스케이 주식회사 화합물, 유기 전계 발광 소자 및 표시 장치

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