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WO2022045817A1 - Dérivés de phénanthrène et diodes électroluminescentes organiques comprenant les dérivés - Google Patents

Dérivés de phénanthrène et diodes électroluminescentes organiques comprenant les dérivés Download PDF

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WO2022045817A1
WO2022045817A1 PCT/KR2021/011494 KR2021011494W WO2022045817A1 WO 2022045817 A1 WO2022045817 A1 WO 2022045817A1 KR 2021011494 W KR2021011494 W KR 2021011494W WO 2022045817 A1 WO2022045817 A1 WO 2022045817A1
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carbon atoms
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문준영
이승수
이태균
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SFC Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes
    • 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]
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/156—Hole transporting layers comprising a multilayered structure
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass

Definitions

  • the present invention relates to a phenanthrene derivative compound and a high-efficiency and long-life organic light emitting device comprising the same.
  • an electron injected from an electron injection electrode (cathode electrode) and a hole injected from a hole injection electrode (anode electrode) are combined in an emission layer to form an exciton, and the exciton generates energy
  • an organic light-emitting device has a low driving voltage, high luminance, wide viewing angle, and fast response speed, and is in the spotlight as a next-generation light source because of the advantages that it can be applied to a full-color flat panel light emitting display. .
  • the structure of the organic layer in the device is optimized, and the material constituting each organic layer is a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, an electron blocking material. It should be preceded by a stable and efficient material, but it is still necessary to continuously develop a stable and efficient organic layer structure and each material for an organic light emitting device.
  • the structure of the device capable of improving the light emitting characteristics of the organic light emitting device and the development of a new material supporting the structure are continuously required.
  • an object of the present invention is to provide an organic light emitting compound capable of implementing a highly efficient organic light emitting device by being employed in the organic layer of the device and an organic light emitting device including the same.
  • the present invention provides a compound having a framework structure represented by the following [Formula A] or [Formula B] and an amine group introduced therein.
  • the present invention includes a first electrode, a second electrode facing the first electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer is [Formula A] or [Formula B] It provides an organic light emitting device comprising at least one compound implemented as
  • the organic layer including at least one compound embodied by the [Formula A] or [Formula B] may be a hole transport layer.
  • the phenanthrene derivative compound according to the present invention may be employed as an organic layer in the device, particularly as a hole transport material, thereby realizing a high-efficiency and long-life organic light emitting device.
  • the phenanthrene derivative compound according to the present invention is represented by the following [Formula A] or [Formula B], an amine group is introduced into phenanthrene, and structurally, a characteristic structure is introduced at positions 3 and 10 of phenanthrene.
  • a highly efficient organic light emitting device is produced by introducing an amine structure (arylamine group, heteroarylamine group, arylheteroarylamine group, etc.) at any one of positions 3 and 10 of phenanthrene. can be implemented
  • Form A is characterized in that an aryl group, a heteroaryl group, etc. are introduced at the 10-position of phenanthrene, and an amine structure is introduced through a linking group, etc. at the 3-position.
  • Ar 1 is any one selected from a substituted or unsubstituted C 10 to C 50 aryl group and a substituted or unsubstituted C 1 to C 50 heteroaryl group, and according to an embodiment of the present invention, Ar 1 is aryl In the case of a group, it is structurally characterized in that it does not include phenyl as having 10 or more carbon atoms.
  • L 1 To L 3 are the same as or different from each other and each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 1 to 50 carbon atoms
  • n, o, and p are each independently an integer of 0 to 3, and when L 1 to L 3 are a plurality, they are the same or different from each other.
  • each of L 2 and L 3 may be a single bond or a substituted or unsubstituted arylene group having 6 to 24 carbon atoms, and o+p is an integer of 1 or more.
  • each of L 2 and L 3 may be a single bond, or any one selected from the following [Structural Formula 1] to [Structural Formula 5].
  • R 1 and R 2 are the same as or different from each other and are each independently a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a substituted or unsubstituted C 1 to C 30 hetero A cycloalkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C 1 to C 50 heteroaryl group, a substituted or unsubstituted C 6 to C 30 arylamine group, Any one selected from a substituted or unsubstituted heteroarylamine group having 2 to 30 carbon atoms and a substituted or unsubstituted arylheteroarylamine group having 6 to 30 carbon atoms.
  • R 1 and R 2 are each a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted amine group, a substituted Or it may be any one selected from an unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted fluorenyl group, preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted It may be any one selected from a cyclic naphthyl group, a substituted or unsubstituted phenanthrenyl group, and a substituted or unsubstituted amine group.
  • Forma B is characterized in that an alkyl group, an aryl group, a heteroaryl group, etc. are introduced at the 3 th position of phenanthrene, and an amine structure is introduced through a linking group at the 10 th position.
  • Ar 2 is any one selected from a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, and a substituted or unsubstituted C 1 to C 50 heteroaryl group.
  • Ar 2 may be any one selected from a substituted or unsubstituted phenyl group and a substituted or unsubstituted naphthyl group.
  • L 4 To L 6 are the same as or different from each other and each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 1 to 50 carbon atoms
  • m, q, and r are each independently an integer of 0 to 3
  • L 4 to L 6 are the same as or different from each other when a plurality of L 4 to L 6 are each.
  • each of L 5 and L 6 may be a single bond or a substituted or unsubstituted C6-C24 arylene group, and q+r is an integer of 1 or more.
  • each of L 5 and L 6 may be a single bond or any one selected from the following [Structural Formula 1] to [Structural Formula 5].
  • R 3 and R 4 are the same as or different from each other and each independently represent a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, or a substituted or unsubstituted C 1 to C 30 hetero
  • R 3 and R 4 are each a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted amine group, a substituted Or it may be any one selected from an unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted fluorenyl group, preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted It may be any one selected from a cyclic naphthyl group, a substituted or unsubstituted phenanthrenyl group, and a substituted or unsubstituted amine group.
  • L 1 to L 6 , Ar 1 to Ar 2 and R 1 to R 4 are deuterium, cyano group, halogen group, hydroxyl group, nitro group, amino group, alkyl group, halogenated at least one substituent selected from the group consisting of an alkyl group, a cycloalkyl group, a heterocycloalkyl group, an aryl group, a heteroaryl group, an alkoxy group, an arylamine group, a heteroarylamine group, an arylheteroarylamine group, an alkylsilyl group and an arylsilyl group It means that it is substituted with, or substituted with a substituent to which two or more of the substituents are connected, or does not have any substituents.
  • the carbon number range of the alkyl group or aryl group in the 'substituted or unsubstituted alkyl group having 1 to 30 carbon atoms', 'substituted or unsubstituted aryl group having 6 to 50 carbon atoms', etc. considers the portion in which the substituent is substituted. It refers to the total number of carbon atoms constituting the alkyl part or the aryl part when viewed as unsubstituted.
  • a phenyl group substituted with a butyl group at the para-position corresponds to an aryl group having 6 carbon atoms substituted with a butyl group having 4 carbon atoms.
  • the meaning that adjacent groups are bonded to each other to form a ring means that adjacent groups can be bonded to each other to form a substituted or unsubstituted alicyclic or aromatic ring, and 'adjacent substituents'
  • the substituent may refer to a substituent substituted on an atom directly connected to the substituted atom, a substituent located three-dimensionally closest to the substituent, or another substituent substituted with the atom in which the substituent is substituted.
  • two substituents substituted at an ortho position in a benzene ring and two substituents substituted at the same carbon in an aliphatic ring may be interpreted as 'adjacent substituents'.
  • the alkyl group may be linear or branched, and specific examples thereof include a methyl group, an ethyl group, a propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1- Methylpentyl group, 2-methylpentyl group, 4-methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group ,
  • the alkenyl group includes a straight or branched chain, and may be further substituted by other substituents, specifically, a vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-bute Nyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1-butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group , 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl -1-yl) a vinyl-1-yl group, a stilbenyl group, a styrenyl group, and the like, but are not limited thereto.
  • substituents specifically, a vinyl group,
  • the alkynyl group also includes a straight or branched chain, and may be further substituted by other substituents, and may include ethynyl, 2-propynyl, and the like, but limited thereto. it doesn't happen
  • the aromatic hydrocarbon ring or the aryl group may be monocyclic or polycyclic, and examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, a stilbene group, and the polycyclic aryl group includes a naphthyl group.
  • anthracenyl group phenanthrenyl group
  • pyrenyl group perylenyl group
  • tetracenyl group chrysenyl group
  • fluorenyl group acenaphthacenyl group
  • triphenylene group fluoranthene group, etc.
  • the aromatic heterocyclic or heteroaryl group is an aromatic ring containing at least one heteroatom, for example, a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, and an oxadia group.
  • the aliphatic hydrocarbon ring is a non-aromatic ring, which means a ring consisting only of carbon and hydrogen atoms, and includes, for example, a monocyclic or polycyclic ring, and may be further substituted by other substituents, and the polycyclic is another
  • the other ring group may be an aliphatic hydrocarbon ring, but may be a different type of ring group, for example, an aliphatic heterocycle, an aryl group, a heteroaryl group, or the like.
  • the aliphatic heterocycle refers to an aliphatic ring including at least one of heteroatoms, and includes heteroatoms such as O, S, Se, N or Si, and also includes monocyclic or polycyclic rings, and other substituents may be further substituted by, and polycyclic refers to a group in which a heterocycloalkyl, heterocycloalkane, heterocycloalgen group, etc. is directly connected or condensed with another ring group, and the other ring group may be an aliphatic heterocycle, It may be another type of cyclic group, such as an aliphatic hydrocarbon ring, an aryl group, a heteroaryl group, and the like.
  • the aliphatic aromatic mixed ring means a ring in which two or more rings are connected to each other and condensed, and an aliphatic ring and an aromatic ring are condensed to have non-aromaticity as a whole, and also polycyclic aliphatic aromatic It may include a hetero atom selected from N, O, P and S in addition to C in the mixed ring.
  • the alkoxy group may be specifically methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, iso-amyloxy, hexyloxy, and the like, but is not limited thereto.
  • the silyl group may be -SiH 3 , an alkylsilyl group, an arylsilyl group, an alkylarylsilyl group, an arylheteroarylsilyl group, and the like, and specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, and trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, and dimethylfurylsilyl.
  • the amine group may be -NH 2 , an alkylamine group, an arylamine group, an arylheteroarylamine group, etc.
  • the arylamine group means an amine substituted with aryl
  • the alkylamine group means an amine substituted with an alkyl
  • the aryl heteroarylamine group means an amine substituted with aryl and heteroaryl groups, and examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or There is an unsubstituted triarylamine group
  • the aryl group and heteroaryl group in the arylamine group and the arylheteroarylamine group may be a monocyclic aryl group or a monocyclic heteroaryl group, and may be a polycyclic aryl group or a polycyclic heteroaryl group.
  • the aryl group, the arylamine group comprising two or more heteroaryl groups is a monocyclic aryl group (heteroaryl group), a polycyclic aryl group (heteroaryl group), or a monocyclic aryl group (hetero) aryl group) and a polycyclic aryl group (heteroaryl group) may be included at the same time.
  • the aryl group and the heteroaryl group in the arylamine group and the arylheteroarylamine group may be selected from the examples of the above-described aryl group and heteroaryl group.
  • the aryl group in the aryloxy group and the arylthioxy group is the same as the above-described aryl group, and specifically, the aryloxy group includes a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5- Dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3-biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4 -Methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group, 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenane and a toryloxy group, a 9-phenanthryloxy group, and the like, and the arylthioxy group includes, but is not limited to, a phenoxy group,
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the phenanthrene derivative compound represented by [Formula A] according to the present invention may be any one selected from the following [Compound 1] to [Compound 54], through which a specific substituent can be clearly identified, ,
  • the scope of [Formula A] according to the present invention is not limited thereby.
  • the phenanthrene derivative compound represented by [Formula B] according to the present invention may be any one selected from the following [Compound 101] to [Compound 169], and specific substituents can be clearly identified through this, but , The scope of [Formula B] according to the present invention is not limited thereby.
  • the compound represented by [Formula A] or [Formula B] according to the present invention is a compound in which a characteristic structure is introduced at positions 3 and 10 of phenanthrene, respectively, of a skeleton and a substituent It is possible to synthesize an organic light emitting material having unique properties, and through this, a high efficiency and long lifespan organic light emitting device can be realized.
  • an organic light emitting device comprising a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer has the [Formula A] Or it may include at least one organic light emitting compound according to the present invention represented by [Formula B].
  • the organic layer includes at least one of an electron injection layer, an electron transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, and a light emitting layer, wherein at least one of the layers is the [Formula A] or [Formula A] B] characterized in that it contains an organic light emitting compound represented by.
  • the hole transport layer is characterized in that it comprises an organic light emitting compound represented by the [Formula A] or [Formula B].
  • the hole transport layer may be formed of a plurality of hole transport layers, and the hole transport layer of any one of the plurality of hole transport layers is an organic compound represented by [Formula A] or [Formula B]. It is characterized in that it contains a light-emitting compound.
  • the organic light emitting diode may have a structure including a first electrode and a second electrode and an organic layer disposed therebetween, and according to the present invention [Formula A] or [Formula B] Except that the organic light emitting compound of the device is used in the organic layer of the device, it can be manufactured using a conventional device manufacturing method and material.
  • the organic layer of the organic light emitting device may have a single-layer structure, but may have a multi-layered structure in which two or more organic layers are stacked.
  • it may have a structure including a hole injection layer, a hole transport layer, a hole blocking layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, and the like, and each layer may consist of a plurality of layers.
  • the present invention is not limited thereto and may include a smaller number or a larger number of organic layers.
  • the organic light emitting device includes a light emitting layer interposed between the first electrode and the second electrode, and the light emitting layer consists of a host and a dopant, and in this case, the content of the dopant in the light emitting layer is usually It may be selected from about 0.01 to about 20 parts by weight based on 100 parts by weight of the host, but is not limited thereto.
  • the host may be an anthracene derivative represented by the following [Formula C].
  • R 11 to R 18 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted C A cycloalkyl group of 3 to 30, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, cya selected from a no group, a nitro group and a halogen group.
  • Ar 5 and Ar 6 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms.
  • L 11 and L 12 are the same as or different from each other, and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms and a substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms.
  • n 11 and n 12 are integers of 1 to 2, and when n 11 and n 12 are 2, each of the linking groups L 11 and L 12 is the same as or different from each other.
  • 'substitution' in the 'substituted or unsubstituted' in [Formula C] is deuterium, cyano group, halogen group, hydroxyl group, nitro group, C1-C24 alkyl group, C1-C24 halogenated Alkyl group, C2-C24 alkenyl group, C2-C24 alkynyl group, C1-C24 heteroalkyl group, C6-C24 aryl group, C7-C24 arylalkyl group, C2-C24 heteroaryl group , C2-C24 heteroarylalkyl group, C1-C24 alkoxy group, C1-C24 alkylamino group, C6-C24 arylamino group, C1-C24 heteroarylamino group, C1-C24 alkylsilyl It means being substituted with one or more substituents selected from the group consisting of a group, an arylsilyl group having 6 to 24 carbon atoms
  • the dopant may be made of any one or more selected from the following [Formula D1] to [Formula D10].
  • a 31 , A 32 , E 1 and F 1 are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms or a substituted or unsubstituted aromatic heterocycle having 2 to 40 carbon atoms.
  • L 21 to L 32 are the same as or different from each other, and each independently represents a single bond, a substituted or unsubstituted C 1 to C 60 alkylene group, a substituted or unsubstituted C 2 to C 60 alkenylene group, substituted or unsubstituted A substituted or unsubstituted C2 to C60 alkynylene group, a substituted or unsubstituted C3 to C60 cycloalkylene group, a substituted or unsubstituted C2 to C60 heterocycloalkylene group, a substituted or unsubstituted C6 to C60 aryl Any one selected from a ene group and a substituted or unsubstituted C 2 to C 60 heteroarylene group.
  • W and W' are each selected from NR 53 , CR 54 R 55 , SiR 56 R 57 , GeR 58 R 59 , O, S and Se.
  • R 51 to R 59 , Ar 21 to Ar 28 are the same as or different from each other, and each independently represent hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, A substituted or unsubstituted C 2 to C 30 alkenyl group, a substituted or unsubstituted C 2 to C 20 alkynyl group, a substituted or unsubstituted C 3 to C 30 cycloalkyl group, a substituted or unsubstituted C 5 to C 30 cyclo Alkenyl group, substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, substituted or unsubstituted heterocycloalkyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted carbon number A 6 to 30 ary
  • R 51 and R 52 may be connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring, and the carbon atoms of the formed alicyclic or aromatic monocyclic or polycyclic ring are N, O, P, Si, S , Ge, Se, and Te may be substituted with any one or more heteroatoms selected from.
  • p11 to p14, r11 to r14, and s11 to s14 are each an integer of 1 to 3, and when each of these is 2 or more, each of the linking groups L 21 to L 32 is the same or different from each other.
  • x1 is 1, and y1, z1, and z2 are each an integer from 0 to 1.
  • Ar 21 and Ar 22 , Ar 23 and Ar 24 , Ar 25 and Ar 26 , and Ar 27 and Ar 28 may be connected to each other to form a ring.
  • T1 to T3 are the same as or different from each other, and each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocycle having 2 to 40 carbon atoms.
  • Y 1 is any one selected from NR 61 , CR 62 R 63 , O, S and SiR 64 R 65
  • Y 2 is any one selected from NR 66 , CR 67 R 68 , O, S and SiR 69 R 70 .
  • R 61 to R 70 are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted C 1 to C 30 alkyl group, a substituted or unsubstituted C 6 to C 50 aryl group, a substituted or unsubstituted A cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted Or an unsubstituted C1-C30 alkylthio group, a substituted or unsubstituted C6-C30 arylthioxy group, a substituted or unsubstituted C1-C30 alkylamine group, a substituted or unsubstituted C6-C30 of an
  • Each of R 61 to R 70 may be combined with one or more rings selected from T1 to T3 to further form an alicyclic or aromatic monocyclic or polycyclic ring.
  • Y 4 is any one selected from NR 61 , CR 62 R 63 , O, S and SiR 64 R 65
  • Y 5 is any one selected from NR 66 , CR 67 R 68 , O, S and SiR 69
  • R 70 and Y 6 is any one selected from NR 71 , CR 72 R 73 , O, S and SiR 74 R 75 .
  • R 61 to R 75 is the same as the definition of R 61 to R 70 in [Formula D3].
  • Y 6 is any one selected from NR 61 , CR 62 R 63 , O, S and SiR 64 R 65 ,
  • R 61 to R 65 , R 71 to R 72 are each the same as the definition of R 61 to R 70 in [Formula D3],
  • R 71 and R 72 are each connected to each other to additionally form an alicyclic or aromatic monocyclic or polycyclic ring, or combine with any one of the T7 to T9 rings to further form an alicyclic or aromatic monocyclic or polycyclic ring can do.
  • Y is any one selected from NR 3 , CR 4 R 5 , O, S, and Se, and R 3 to R 5 are the same as defined for R 61 to R 70 in [Formula D3], respectively.
  • Each of R 3 to R 5 may be combined with the Q 2 ring or the Q 3 ring to further form an alicyclic or aromatic monocyclic or polycyclic ring.
  • the R 4 and R 5 may be connected to each other to further form an alicyclic or aromatic monocyclic or polycyclic ring.
  • the ring formed by Cy1 has a nitrogen (N) atom, an aromatic carbon atom in the Q1 ring to which the nitrogen (N) atom is bonded, and an aromatic carbon atom in the Q1 ring to be bonded to Cy1, substituted or unsubstituted carbon number 1 to 10 alkylene groups.
  • 'Cy2' may be added to Cy1 to form a saturated hydrocarbon ring, and the ring formed by Cy2 may have 1 to 10 substituted or unsubstituted carbon atoms, except for carbon atoms included in Cy1.
  • the ring formed by Cy3 is an aromatic carbon atom in the Q3 ring to be bonded to Cy3, an aromatic carbon atom in Q3 to be bonded to a nitrogen (N) atom, a nitrogen (N) atom, the nitrogen (N) ) is a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, except for carbon atoms in Cy1 to which the atoms are bonded
  • 'substitution' in the 'substituted or unsubstituted' in the [Formula D1] to [Formula D10] is deuterium, a cyano group, a halogen group, a hydroxyl group, a nitro group, an alkyl group having 1 to 24 carbon atoms, 1 to 24 carbon atoms of a halogenated alkyl group, an alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, a cycloalkyl group having 3 to 24 carbon atoms, a heteroalkyl group having 1 to 24 carbon atoms, an aryl group having 6 to 24 carbon atoms, an aryl group having 7 to 24 carbon atoms.
  • an anode is formed by coating a material for an anode electrode on a substrate.
  • a substrate used in a conventional organic light emitting device is used, and an organic substrate or a transparent plastic substrate excellent in transparency, surface smoothness, handling and water resistance is preferable.
  • transparent and excellent indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), etc. are used as a material for the anode electrode.
  • a hole injection layer is formed by vacuum thermal evaporation or spin coating of a hole injection layer material on the anode electrode, and then vacuum thermal evaporation or spin coating of a hole transport layer material on the hole injection layer to form a hole transport layer .
  • the hole injection layer material may be used without particular limitation as long as it is commonly used in the art, and as a specific example, 2-TNATA [4,4',4"-tris(2-naphthylphenyl-phenylamino)-triphenylamine] , NPD [N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine)], TPD [N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'- biphenyl-4,4'-diamine], DNTPD [N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine ] HAT-CN [1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile] and the like can be used.
  • the compound according to the present invention may be employed, and in particular, in the case of configuring a plurality of hole transport layers in the organic light emitting device in the present invention, for example, as a first hole transport layer and a second hole transport layer
  • one layer employs the compound according to the present invention, and the other layer is not particularly limited as long as it is commonly used in the art.
  • N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine (TPD) or N,N'-di( Naphthalen-1-yl)-N,N'-diphenylbenzidine ( ⁇ -NPD) or the like may be used, and a hole transport material conventionally used at the time of deriving the present invention may be used.
  • a hole auxiliary layer and a light emitting layer may be sequentially stacked on the hole transport layer, and a thin film may be formed by selectively forming a hole blocking layer on the light emitting layer by a vacuum deposition method or a spin coating method.
  • the hole blocking layer serves to prevent this problem by using a material having a very low HOMO (Highest Occupied Molecular Orbital) level because the lifetime and efficiency of the device are reduced when holes are introduced into the cathode through the organic light emitting layer.
  • the hole blocking material used is not particularly limited, but it should have an ionization potential higher than that of a light emitting compound while having an electron transport ability, and typically BAlq, BCP, TPBI, etc. may be used.
  • BAlq As the material used for the hole blocking layer, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq 2 , OXD-7, Liq, etc. may be used, but is not limited thereto.
  • an electron injection layer is formed, and a cathode forming metal is vacuum thermally deposited on the electron injection layer to form a cathode electrode.
  • An organic light emitting diode according to an embodiment is completed.
  • lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver ( Mg-Ag) may be used, and in order to obtain a top light emitting device, a transmissive cathode using ITO or IZO may be used.
  • the electron transport layer material serves to stably transport electrons injected from the cathode, and a known electron transport material may be used.
  • known electron transport materials include quinoline derivatives, in particular tris(8-quinolinolate)aluminum (Alq3), TAZ, BAlq, beryllium bis(benzoquinolin-10- Materials such as olate: Bebq2) and oxadiazole derivatives PBD, BMD, and BND may be used.
  • each of the organic layers may be formed by a single molecule deposition method or a solution process, wherein the deposition method evaporates a material used as a material for forming each layer through heating in a vacuum or low pressure state. It refers to a method of forming a thin film, and the solution process mixes a material used as a material for forming each layer with a solvent, and uses it inkjet printing, roll to roll coating, screen printing, spray coating, dip coating, spin coating It refers to a method of forming a thin film through a method such as this.
  • the organic light emitting diode according to the present invention can be used in a device selected from a flat panel display device, a flexible display device, a device for flat panel lighting of a single color or white color, and a device for a flexible lighting device of a single color or white color.
  • N-(4-(naphthalen-2-yl)phenyl)-[1,1':4',1"-terphenyl]-4-amine (22.0 g, 0.049 mol) and 1-Bromo-4-iodobenzene (15.3 g, 0.054 mol), Pd(OAc) 2 (0.11 g, 0.1 mmol), Xantphos (0.28 g, 0.1 mmol), STB (5.20 g, 0.054 mol), and toluene (220 mL) were placed in a reactor and stirred at 100 °C overnight. After EA/H 2 O extraction and concentration of the organic layer, column purification (MC/Hep) was performed to synthesize Intermediate 10-1 (21 g, yield 70.9%).
  • the base pressure was made to 1 ⁇ 10 -7 torr, and on the ITO, DNTPD (450 ⁇ ), [Compound G] (200 ⁇ ), as a second hole transport layer material in the present invention
  • the compounds (50 ⁇ ) described in the following [Table 1] were respectively formed into a film.
  • [Compound 313]:[D280] was mixed in the light emitting layer in a weight ratio (97:3) to form a film (200 ⁇ ), and then [Compound E-2] (300 ⁇ ) as an electron transport layer and [Compound E-2] (300 ⁇ ) as an electron injection layer E-1] (10 ⁇ ) and Al (1000 ⁇ ) were formed in the order to prepare an organic light emitting diode.
  • the emission characteristics of the organic light emitting device were measured at 0.4 mA.
  • an organic light emitting device was prepared in the same manner except that the following [Compound B] to [Compound E] were used instead of the compound according to the present invention for the second hole transport layer compound, and the organic light emitting device was prepared.
  • the light emitting characteristics of the light emitting device were measured at 0.4 mA.
  • the [Formula A] compound (Examples 1 to 6) according to the present invention is a comparative compound [Formula B] compounds (Examples 7 to 14) according to the present invention have significantly improved long life characteristics compared to conventional devices (Comparative Examples 1 to 4) employing ), it can be seen that it has better efficiency characteristics and significantly improved long life characteristics.
  • the phenanthrene derivative compound according to the present invention is employed as an organic layer in the device, particularly as a hole transport material, and thus can realize a high-efficiency and long-life organic light emitting device, so that a flat panel display device, a flexible display device, a device for flat panel lighting of a single color or a white color and a single color or white color It can be usefully used industrially, for example, in a device for flexible lighting.

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  • Organic Chemistry (AREA)
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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne des dérivés de phénanthrène qui peuvent être utilisés dans une couche organique dans des diodes électroluminescentes organiques, et des diodes électroluminescentes organiques hautement efficaces et à longue durée de vie les comprenant. Étant donné que des diodes électroluminescentes organiques hautement efficaces et à longue durée de vie peuvent être produites en employant les dérivés phénanthrène de la présente invention en tant que matériau de transport de trous dans les diodes, le dérivé de phénanthrène peut être utilisé industriellement dans un dispositif d'affichage à écran plat, un dispositif d'affichage flexible, un dispositif d'éclairage à panneau plat monochrome ou blanc, un dispositif d'éclairage flexible monochrome ou blanc et des dispositifs similaires.
PCT/KR2021/011494 2020-08-28 2021-08-27 Dérivés de phénanthrène et diodes électroluminescentes organiques comprenant les dérivés Ceased WO2022045817A1 (fr)

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