WO2021172965A1 - Composé dérivé aromatique polycyclique et dispositif électroluminescent organique utilisant celui-ci - Google Patents

Composé dérivé aromatique polycyclique et dispositif électroluminescent organique utilisant celui-ci Download PDF

Info

Publication number
WO2021172965A1
WO2021172965A1 PCT/KR2021/002534 KR2021002534W WO2021172965A1 WO 2021172965 A1 WO2021172965 A1 WO 2021172965A1 KR 2021002534 W KR2021002534 W KR 2021002534W WO 2021172965 A1 WO2021172965 A1 WO 2021172965A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
formula
carbon atoms
Prior art date
Application number
PCT/KR2021/002534
Other languages
English (en)
Korean (ko)
Inventor
신봉기
주성훈
양병선
김수진
김지환
조현준
최성은
Original Assignee
에스에프씨 주식회사
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 에스에프씨 주식회사 filed Critical 에스에프씨 주식회사
Publication of WO2021172965A1 publication Critical patent/WO2021172965A1/fr

Links

Classifications

    • 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
    • H10K85/658—Organoboranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • 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
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • 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
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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
    • 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]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers

Definitions

  • the present invention relates to a polycyclic aromatic derivative compound and a high-efficiency, long-life organic light-emitting device with remarkably improved luminous efficiency using the same.
  • an organic light emitting device In an organic light emitting device, electrons injected from an electron injection electrode (cathode electrode) and holes injected from a hole injection electrode (anode electrode) combine in a light emitting layer to form excitons, and the excitons release energy It is a self-luminous device that emits light while emitting light, and such 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 its 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 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 it are continuously required.
  • an object of the present invention is to provide an organic light emitting compound capable of implementing an organic light emitting device with high efficiency and long lifespan by being employed in the organic layer of the device, and an organic light emitting device including the same.
  • the present invention provides an organic light emitting compound represented by the following [Formula A-1] to [Formula A-2] in order to solve the above problems.
  • the compound represented by the [Formula A-1] to [Formula A-2] according to the present invention is characterized in that it necessarily contains at least one of the following [Structural Formula Cy] and/or [Structural Formula Cy-Q3].
  • the present invention includes a first electrode, a second electrode opposite to the first electrode, and an organic layer interposed between the first electrode and the second electrode, wherein the organic layer is [Formula A-1] to [Formula A-1] A-2] provides an organic light emitting device comprising at least one specific polycyclic aromatic compound implemented as.
  • the polycyclic aromatic derivative compound according to the present invention can be employed in the organic layer in the device to realize a high efficiency and long life organic light emitting device.
  • the present invention is included in an organic light emitting device, and relates to a polycyclic aromatic derivative compound represented by the following [Formula A-1] to [Formula A-2], structurally including at least one cyclic ring in the following skeleton structure It is characterized in that, through this, it is possible to implement an organic light emitting device of high efficiency and, in particular, a long lifespan with significantly improved lifespan characteristics.
  • the compound represented by [Formula A-1] to [Formula A-2] according to the present invention is characterized in that it necessarily includes at least one of the following [Structural Formula Cy] and/or [Structural Formula Cy-Q3].
  • Y is NR 1 , CR 2 R 3 , O, S, Se, SiR 4 R 5 and a single bond, and a plurality of Ys are the same as or different from each other.
  • (iii) Z is N or CR 6 , wherein R 6 may be the following [Structural Formula Cy-Q3] as described below, and a plurality of Zs are the same or different, and two or more of the plurality of Zs are CR In the case of 6, two adjacent R 6 may be bonded to the following [Structural Formula Cy].
  • Q 1 and Q 2 are the same as or different from each other, and are each selected from the following [Structural Formula 1] and [Structural Formula 2].
  • Q 3 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms, or a substituted or unsubstituted aromatic heterocycle having 2 to 50 carbon atoms.
  • A is N, CR 7 or SiR 8 , a plurality of A are the same as or different from each other and not connected to each other, V is NR 9 , O, S or Se, and n is an integer from 1 to 10.
  • two adjacent ones of A and V in [Structural Formula 1] may be bonded to the following [Structural Formula Cy]
  • two adjacent ones of V and R in [Structural Formula 2] may be bonded to the following [Structural Formula Cy] .
  • L is a substituted or unsubstituted aliphatic chain or a heteroaliphatic chain.
  • Adjacent substituents in [Structural Formula Cy] may be combined with each other or W to further form an alicyclic or aromatic monocyclic or polycyclic ring.
  • the R, R 1 to R 9 and R 14 to R 19 are the same 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 50 aryl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 2 to C 50 heteroaryl group, substituted or unsubstituted C 1 to C 30 alkoxy group, substituted or unsubstituted an aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylthioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, or a substituted or unsubstituted alkylamine having 1 to 30 carbon atoms group, a substituted or unsubstituted arylamine group having 1 to
  • L, W and Q 3 are the same as the definitions in [Structural Formula 2] and [Structural Formula Cy], respectively, and when R, R 1 to R 9 and R 14 to R 19 are each [Structural Formula Cy-Q3], L , W and Q 3 means to be bound to any one of.
  • R' is 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 3 to C 30 cycloalkyl group, a substituted or unsubstituted A 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, a substituted or unsubstituted alkyltioxy group having 1 to 30 carbon atoms, A substituted or unsubstituted C5-C30 arylthioxy group, a substituted or unsubstituted C1-C30 alkylamine group, a substituted or unsubstituted C5-C30 arylamine group, a substituted or unsubstituted C
  • R, R', R 1 to R 9 and R 14 to R 19 may be bonded to each other or connected to an adjacent substituent to form an alicyclic, aromatic monocyclic or polycyclic ring, and the formed alicyclic, aromatic A carbon atom of the monocyclic or polycyclic ring may be substituted with any one or more heteroatoms selected from N, S, O, Se, Si, B, P and Al.
  • each of R 2 and R 3 , R 4 and R 5 may be connected to each other to form an alicyclic or aromatic monocyclic or polycyclic ring.
  • the compounds represented by [Formula A-1] to [Formula A-2] according to the present invention are Q 1 and Q 2 defined by [Structural Formula 1] or [Structural Formula 2] combined with [Structural Formula Cy] , when a plurality of Z is bonded to [Structural Formula Cy], R, R 1 to R 9 and R 14 to R 19 are [Structural Formula Cy] through [Structural Formula Cy] and/or It is characterized in that it necessarily contains at least one [Structural Formula Cy-Q3].
  • Q 3 is a 5-membered ring or a 6-membered monocyclic ring, or a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 carbon atoms composed of 2 to 5 polycyclic rings, or a substituted or unsubstituted It may be an aromatic heterocyclic ring having 2 to 50 carbon atoms.
  • R 7 is connected to each other and is represented by a ring represented by [Structural Formula Cy].
  • R 14 to R 19 are a substituted or unsubstituted C1-C30 alkyl group, substituted or unsubstituted C6-C50 aryl except for hydrogen and deuterium group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C2 to C50 heteroaryl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C6 to C6 A 30 aryloxy group, a substituted or unsubstituted C 1 to C 30 alkylthioxy group,
  • [Formula A-1] to [Formula A-2] according to the present invention are organic by necessarily including at least one cyclic ring structure having a characteristic structure while having various skeleton structures according to the definition of the skeleton structure and substituents.
  • Various organic layers of the light emitting device satisfy the desired conditions, thereby realizing the organic light emitting device with high efficiency and long life.
  • the term 'substituted or unsubstituted' means that each of the substituents defined above is deuterium, cyano group, halogen group, hydroxyl group, nitro group, alkyl group having 1 to 24 carbon atoms, cyclo having 3 to 24 carbon atoms.
  • the carbon number range of the alkyl group or aryl group in the 'substituted or unsubstituted alkyl group having 1 to 10 carbon atoms', 'substituted or unsubstituted aryl group having 6 to 30 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 positioned closest to the steric structure 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 the number of carbon atoms is not particularly limited, but is preferably 1 to 20.
  • Specific examples include methyl group, ethyl group, 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, 2-
  • 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) vinyl-1-yl group, stilbenyl group, styrenyl group, and the like, but are not limited thereto.
  • substituents specifically, a vinyl group, 1-propenyl 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 is limited thereto. it doesn't happen
  • the cycloalkyl group includes a monocyclic or polycyclic ring, and may be further substituted by another substituent
  • the polycyclic refers to a group in which a cycloalkyl group is directly connected or condensed with another ring group, and the other ring group is a cycloalkyl group.
  • the heterocycloalkyl group includes a heteroatom such as O, S, Se, N or Si, and also includes monocyclic or polycyclic, and may be further substituted by other substituents, and polycyclic means heterocyclo
  • the alkyl group refers to a group directly connected or condensed with another ring group, and the other ring group may be a heterocycloalkyl group, but may be a different type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, or the like.
  • 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, and a stilbene group, and examples of the polycyclic aryl group include a naphthyl group and an anthracenyl group. , phenanthrenyl group, pyrenyl group, perylenyl group, tetracenyl group, chrysenyl group, fluorenyl group, acenaphthacenyl group, triphenylene group, fluoranthene group, etc., but the scope of the present invention is limited only to these examples it's not going to be
  • the heteroaryl group is a heterocyclic group containing heteroatoms, and examples thereof include a thiophene group, a furan group, a pyrrole group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, Bipyridyl group, pyrimidyl group, triazine group, triazole group, acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyrido Pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzooxazole group, benzoimidazole group, benzothiazole
  • 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 refers to a silyl group substituted with alkyl or a silyl group substituted with aryl
  • specific examples of the silyl group include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, and dimethoxyphenylsilyl. , diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethylfurylsilyl, and the like.
  • the amine group may be -NH 2 , an alkylamine group, an arylamine group, etc.
  • the arylamine group means an amine substituted with an aryl
  • the alkylamine group means an amine substituted with an alkyl
  • an arylamine group examples of these include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group
  • the aryl group in the arylamine group may be a monocyclic aryl group, and It may be a cyclic aryl group
  • the arylamine group including two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
  • the aryl group in the arylamine group may be selected from the examples of
  • 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.
  • polycyclic aromatic derivative compound represented by [Formula A-1] to [Formula A-2] according to the present invention may be any one selected from the following [Compound 1] to [Compound 218], through which The substituent may be clearly identified, but the range of [Formula A-1] to [Formula A-2] according to the present invention is not limited thereby.
  • an organic light emitting device comprising a first electrode, a second electrode, and one or more organic layers interposed between the first electrode and the second electrode, wherein the [Formula A- 1] to [Formula A-2] may include at least one organic light emitting compound according to the present invention.
  • the organic light emitting device 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-1] to [Formula A-2], except that the organic light emitting compound of the device is used for 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 according to the present invention may have a single layer structure, but may have a multilayer 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.
  • the present invention is not limited thereto and may include a smaller number or a larger number of organic layers, and the preferred organic layer structure of the organic light emitting device according to the present invention will be described in more detail in the following Examples.
  • the organic light emitting device includes an anode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode, and if necessary, may further include a hole injection layer between the anode and the hole transport layer, and also between the electron transport layer and the cathode It may further include an injection layer, in addition to that, it is also possible to further form an intermediate layer of one or two layers, a hole blocking layer or an electron blocking layer may be further formed, and an organic layer having various functions according to the characteristics of the device. may further include.
  • the organic light emitting device is characterized in that it contains an anthracene derivative represented by the following [Formula C] as a host compound in the light emitting layer.
  • R 21 to R 28 are the same as or different from each other, and are the same as defined for R in [Formula A-1] to [Formula A-2].
  • Ar 9 and Ar 10 are the same or different from each other, and each independently represents 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 alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted cycloalkenyl group having 5 to 30 carbon atoms, a substituted or unsubstituted 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 un
  • L 13 is a single bond, or any one selected from a substituted or unsubstituted C6 to C20 arylene group, or a substituted or unsubstituted C2 to C20 heteroarylene group, preferably a single bond, or It may be a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, k is an integer of 1 to 3, but when k is 2 or more, each L 13 is the same or different from each other.
  • Ar 9 of the [Formula C] is characterized in that it is a substituent represented by the following [Formula C-1].
  • R 31 to R 35 are the same or different, and are the same as defined for R in [Formula A-1] to [Formula A-2], and combine with neighboring substituents to form a saturated or unsaturated ring have.
  • the [Formula C] employed in the organic light emitting device according to the present invention may be any one specifically selected from the following [Formula C1] to [Formula C57].
  • 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.
  • a material for the anode electrode indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), etc., which are transparent and have excellent conductivity, are used.
  • 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 a hole transport layer is formed by vacuum thermal evaporation or spin coating of a hole transport layer material on the hole injection 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 ] can be used.
  • the hole transport layer material is also not particularly limited as long as it is commonly used in the art, for example, 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), etc. can be used.
  • TPD N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1- Biphenyl]-4,4'-diamine
  • ?-NPD N,N'-di(naphthalen-1-yl)-N,N'-diphenylbenzidine
  • a hole auxiliary layer and a light emitting layer are sequentially stacked on the hole transport layer, and a hole blocking layer is selectively deposited on the light emitting layer by a vacuum deposition method or a spin coating method to form a thin film.
  • 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 has an electron transport ability and has an ionization potential higher than that of a light emitting compound, and typically BAlq, BCP, TPBI, etc. may be used.
  • Examples of the material used for the hole blocking layer include, but are not limited to, BAlq, BCP, Bphen, TPBI, NTAZ, BeBq 2 , OXD-7, Liq, and the like.
  • 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), ADN, and oxadiazole derivatives PBD, BMD, BND, etc. may be used.
  • each of the organic layers may be formed by a monomolecular 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, for example.
  • 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 a white color, and a device for a flexible lighting device of a single color or a white color.
  • the light emitting area of the ITO glass was patterned to have a size of 2 mm ⁇ 2 mm and then washed. After mounting the ITO glass in a vacuum chamber, the base pressure was set to 1 ⁇ 10 -7 torr, and then DNTPD (700 ⁇ ) and [Formula G] (250 ⁇ ) were formed on the ITO in this order.
  • An organic light emitting device was prepared by forming a film in the order of 300 ⁇ , 5 ⁇ , and Al (1000 ⁇ ) of [Formula E-1] as an electron injection layer at a ratio of 1:1. 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 host compound and dopant compound described in Comparative Examples 1 to 3 of Table 1 were used instead of the compound according to the present invention in the light emitting layer, and The luminescence characteristics were measured at 0.4 mA.
  • the structures of BH1, BH2, BD1, and BD2 used in Comparative Examples 1 to 3 are as follows.
  • Example 15 BH1 compound 132 3.5 9.77 208 Comparative Example 1 BH1 BD1 3.5 7.81 125 Comparative Example 2 BH1 BD2 3.5 8.03 128 Comparative Example 1 BH1 compound 28
  • the organic light emitting device employing the compound according to the present invention as a dopant material in the light emitting layer is a device employing a compound that contrasts with the characteristic structure of the compound according to the present invention (comparison Compared to Examples 1 to 3), it has excellent light emitting characteristics such as significantly improved lifespan characteristics and external quantum efficiency.
  • the polycyclic aromatic derivative compound according to the present invention is employed in the organic layer in the device to realize high efficiency and long-life organic light emitting device, so a flat panel display device, a flexible display device, a monochromatic or white flat panel lighting device, and a monochromatic or white flexible lighting device And it can be usefully utilized industrially, such as a display device for a vehicle.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • High Energy & Nuclear Physics (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne : un composé dérivé aromatique polycyclique qui peut être utilisé dans diverses couches organiques dans des dispositifs électroluminescents organiques ; et un dispositif électroluminescent organique présentant une efficacité élevée et une longue durée de vie, qui est amélioré considérablement en termes d'efficacité lumineuse en comprenant le composé dérivé aromatique polycyclique. La présente invention peut être utilisée efficacement dans des applications industrielles, tels que des dispositifs d'affichage plats, des dispositifs d'affichage flexibles, des dispositifs d'éclairage plats monochromes ou blancs, des dispositifs d'éclairage flexibles monochromes ou blancs, et des dispositifs d'affichage pour véhicule.
PCT/KR2021/002534 2020-02-28 2021-03-02 Composé dérivé aromatique polycyclique et dispositif électroluminescent organique utilisant celui-ci WO2021172965A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20200025199 2020-02-28
KR10-2020-0025199 2020-02-28

Publications (1)

Publication Number Publication Date
WO2021172965A1 true WO2021172965A1 (fr) 2021-09-02

Family

ID=77491944

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2021/002534 WO2021172965A1 (fr) 2020-02-28 2021-03-02 Composé dérivé aromatique polycyclique et dispositif électroluminescent organique utilisant celui-ci

Country Status (2)

Country Link
KR (1) KR102467516B1 (fr)
WO (1) WO2021172965A1 (fr)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113045595A (zh) * 2021-02-05 2021-06-29 吉林奥来德光电材料股份有限公司 多环芳族系化合物、其制备方法、发光材料、发光层和有机电致发光器件
CN114989200A (zh) * 2022-04-29 2022-09-02 广州追光科技有限公司 含硼氮化合物及其在有机电子器件中的应用
CN116874517A (zh) * 2023-09-08 2023-10-13 浙江华显光电科技有限公司 含硒吩化合物及其在有机发光装置的应用
CN117209461A (zh) * 2023-11-09 2023-12-12 浙江华显光电科技有限公司 一种有机光电化合物、具有该化合物的组合物及有机发光装置
CN117946146A (zh) * 2024-03-27 2024-04-30 浙江华显光电科技有限公司 含咪唑及衍生基团的硼氮化合物、有机电致发光器件及应用
CN114989200B (zh) * 2022-04-29 2024-06-04 广州追光科技有限公司 含硼氮化合物及其在有机电子器件中的应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190101900A (ko) * 2018-02-23 2019-09-02 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
US20190322623A1 (en) * 2018-12-26 2019-10-24 Wuhan Tianma Micro-Electronics Co., Ltd. Compound, display panel, and display apparatus
KR20200010130A (ko) * 2018-07-19 2020-01-30 주식회사 엘지화학 다환 화합물 및 이를 포함하는 유기 발광 소자
CN110790782A (zh) * 2019-11-11 2020-02-14 北京大学深圳研究生院 一种深蓝色有机发光材料及其制备方法与应用
KR20200019272A (ko) * 2018-07-24 2020-02-24 머티어리얼사이언스 주식회사 유기 전계 발광 소자

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102094830B1 (ko) * 2018-11-30 2020-03-30 에스에프씨 주식회사 다환 방향족 유도체 화합물 및 이를 이용한 유기발광소자
US20230096132A1 (en) * 2019-04-22 2023-03-30 Kwansei Gakuin Educational Foundation Cycloalkane-fused polycyclic aromatic compound

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190101900A (ko) * 2018-02-23 2019-09-02 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20200010130A (ko) * 2018-07-19 2020-01-30 주식회사 엘지화학 다환 화합물 및 이를 포함하는 유기 발광 소자
KR20200019272A (ko) * 2018-07-24 2020-02-24 머티어리얼사이언스 주식회사 유기 전계 발광 소자
US20190322623A1 (en) * 2018-12-26 2019-10-24 Wuhan Tianma Micro-Electronics Co., Ltd. Compound, display panel, and display apparatus
CN110790782A (zh) * 2019-11-11 2020-02-14 北京大学深圳研究生院 一种深蓝色有机发光材料及其制备方法与应用

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113045595A (zh) * 2021-02-05 2021-06-29 吉林奥来德光电材料股份有限公司 多环芳族系化合物、其制备方法、发光材料、发光层和有机电致发光器件
CN114989200A (zh) * 2022-04-29 2022-09-02 广州追光科技有限公司 含硼氮化合物及其在有机电子器件中的应用
CN114989200B (zh) * 2022-04-29 2024-06-04 广州追光科技有限公司 含硼氮化合物及其在有机电子器件中的应用
CN116874517A (zh) * 2023-09-08 2023-10-13 浙江华显光电科技有限公司 含硒吩化合物及其在有机发光装置的应用
CN116874517B (zh) * 2023-09-08 2023-12-01 浙江华显光电科技有限公司 含硒吩化合物及其在有机发光装置的应用
CN117209461A (zh) * 2023-11-09 2023-12-12 浙江华显光电科技有限公司 一种有机光电化合物、具有该化合物的组合物及有机发光装置
CN117209461B (zh) * 2023-11-09 2024-03-22 浙江华显光电科技有限公司 一种有机光电化合物、具有该化合物的组合物及有机发光装置
CN117946146A (zh) * 2024-03-27 2024-04-30 浙江华显光电科技有限公司 含咪唑及衍生基团的硼氮化合物、有机电致发光器件及应用

Also Published As

Publication number Publication date
KR102467516B1 (ko) 2022-11-16
KR20210110233A (ko) 2021-09-07

Similar Documents

Publication Publication Date Title
WO2021080368A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2021172965A1 (fr) Composé dérivé aromatique polycyclique et dispositif électroluminescent organique utilisant celui-ci
WO2021075856A1 (fr) Composé polycyclique et dispositif électroluminescent organique l'utilisant
WO2021086148A1 (fr) Composé polycyclique et dispositif électroluminescent organique l'utilisant
WO2020101395A1 (fr) Nouveau composé de bore, et dispositif électroluminescent organique le comprenant
WO2019160315A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique le comprenant
WO2021187924A1 (fr) Dispositif organique électroluminescent utilisant des composés aromatiques polycycliques
WO2021071345A2 (fr) Composé polycyclique et dispositif électroluminescent organique utilisant ce composé
WO2021141378A1 (fr) Composé dérivé aromatique polycyclique et dispositif électroluminescent organique utilisant celui-ci
WO2022103018A1 (fr) Composé polycyclique et dispositif électroluminescent organique l'utilisant
WO2019108033A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2021015417A1 (fr) Composés électroluminescents organiques et dispositif électroluminescent organique
WO2022119297A1 (fr) Composé polycyclique et dispositif électroluminescent organique utilisant un tel composé
WO2019177393A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2021150026A1 (fr) Composé dérivé polycyclique aromatique et dispositif électroluminescent organique l'utilisant
WO2021091173A1 (fr) Nouveau composé et dispositif électroluminescent organique faisant appel à celui-ci
WO2021066351A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2021150080A1 (fr) Composé dérivé polycyclique aromatique et dispositif électroluminescent organique l'utilisant
WO2020153792A1 (fr) Composé et diode électroluminescente organique le comprenant
WO2020101397A1 (fr) Composé hétérocyclique et diode électroluminescente organique le comprenant
WO2022019414A1 (fr) Composé d'un dérivé polycyclique aromatique et élément électroluminescent organique l'utilisant
WO2023128521A1 (fr) Dispositif électroluminescent organique
WO2022191570A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
WO2021015594A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique
WO2021066350A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21761802

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21761802

Country of ref document: EP

Kind code of ref document: A1