WO2022080927A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

Info

Publication number
WO2022080927A1
WO2022080927A1 PCT/KR2021/014328 KR2021014328W WO2022080927A1 WO 2022080927 A1 WO2022080927 A1 WO 2022080927A1 KR 2021014328 W KR2021014328 W KR 2021014328W WO 2022080927 A1 WO2022080927 A1 WO 2022080927A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
layer
formula
Prior art date
Application number
PCT/KR2021/014328
Other languages
English (en)
Korean (ko)
Inventor
조우진
차용범
홍성길
김동헌
이성재
Original Assignee
주식회사 엘지화학
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 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN202180050217.1A priority Critical patent/CN115916773A/zh
Publication of WO2022080927A1 publication Critical patent/WO2022080927A1/fr

Links

Images

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
    • H10K85/649—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D409/12—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 chain containing hetero atoms as chain links
    • 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
    • H10K85/657—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]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers

Definitions

  • the present invention relates to a compound and an organic light emitting device comprising the same.
  • the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, etc.
  • Patent Document 1 Korean Patent Publication No. 10-2000-0051826
  • An object of the present invention is to provide a compound and/or an organic light emitting device comprising the same.
  • An exemplary embodiment of the present invention provides a compound represented by the following formula (1).
  • X is O or S
  • Ar is a substituted or unsubstituted C10 to C30 alkyl group; a substituted or unsubstituted aryl group having 10 to 30 carbon atoms; Or a substituted or unsubstituted C10 to C30 heterocyclic group,
  • L is a direct bond; Or a substituted or unsubstituted arylene group,
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combined with an adjacent group to form a substituted or unsubstituted ring,
  • r1 to r5 are each an integer of 0 to 4,
  • another embodiment of the present invention is a positive electrode; cathode; and an organic material layer provided between the anode and the cathode, wherein the organic material layer includes the compound represented by Formula 1 above.
  • the compound according to an exemplary embodiment of the present invention may be used as a material of an organic material layer of an organic light emitting device.
  • the compound according to an exemplary embodiment of the present invention may be used as a material for an electron blocking layer of an organic light emitting device.
  • the compound according to an exemplary embodiment of the present invention may be included in an organic light emitting device to improve device characteristics such as low driving voltage, excellent efficiency characteristics, or excellent lifespan characteristics.
  • FIG. 1 illustrates an organic light emitting diode according to an exemplary embodiment of the present invention.
  • FIG. 2 illustrates an organic light emitting device according to another exemplary embodiment of the present invention.
  • An exemplary embodiment of the present invention provides a compound represented by the following formula (1).
  • X is O or S
  • Ar is a substituted or unsubstituted C10 to C30 alkyl group; a substituted or unsubstituted aryl group having 10 to 30 carbon atoms; Or a substituted or unsubstituted C10 to C30 heterocyclic group,
  • L is a direct bond; Or a substituted or unsubstituted arylene group,
  • R1 to R5 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combined with an adjacent group to form a substituted or unsubstituted ring,
  • r1 to r5 are each an integer of 0 to 4,
  • An exemplary embodiment of the present invention provides a compound represented by Formula 1 above.
  • the amine group is bonded to the para part of the biphenyl group, and the carbazole group is bonded to the ortho part via a direct bond or a linking group (L) to obtain the highest occupied molecular orbital (HOMO) value. It can be maintained high, thereby reducing an energy barrier with an adjacent light emitting layer, thereby properly maintaining a charge balance.
  • the organic material layer including the compound represented by Formula 1 is used as the electron blocking layer, the generated excitons are trapped in the light emitting layer to prevent light emission leakage, so an organic light emitting device having excellent light emitting efficiency can be implemented. .
  • the compound of Formula 1 is used in the electron blocking layer, the characteristics of long life, low voltage, or high efficiency of the organic light emitting diode are enhanced.
  • substitution means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, a position where the substituent is substitutable, is substituted. , two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, is substituted with a substituent to which two or more of the above exemplified substituents are connected, or does not have any substituents.
  • the "substituent to which two or more substituents are connected" may be an aryl group substituted with an aryl group, a heterocyclic group substituted with an aryl group, an aryl group substituted with an alkyl group, or the like.
  • a ring formed by bonding adjacent groups is a hydrocarbon ring; or a heterocyclic ring.
  • the halogen group may be F, Cl, Br, I, or the like.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specifically, it is preferably 1 to 20 carbon atoms. More specifically, it is preferable that it has 1-10 carbon atoms.
  • tertbutyl group a methyl group; ethyl group; Profile group; n-propyl group; isopropyl group; butyl group; n-butyl group; isobutyl group; tert-butyl group (hereinafter referred to as tertbutyl group); sec-butyl group; 1-methylbutyl group; 1-ethylbutyl 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; cyclohexylmethyl group;
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms.
  • the silyl group may be represented by the formula of -SiRaRbRc, wherein Ra, Rb and Rc are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group is specifically a trimethylsilyl group; triethylsilyl group; t-butyldimethylsilyl group; vinyl dimethyl silyl group; propyldimethylsilyl group; triphenylsilyl group; diphenylsilyl group; There is a phenylsilyl group, but is not limited thereto.
  • the amine group may be represented by -NRdRe, wherein Rd and Re are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted It may be a heteroaryl group, but is not limited thereto.
  • the amine group is selected from the group consisting of an alkylamine group, an alkylarylamine group, an arylamine group, a heteroarylamine group, an alkylheteroarylamine group, and an arylheteroarylamine group, depending on the type of the substituent (Rd, Re) to be bonded.
  • Rd and Re are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted It may be a
  • the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms.
  • the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but preferably 6 to 30 carbon atoms. More specifically, it is preferable that it has 6 to 20 carbon atoms.
  • the monocyclic aryl group includes a phenyl group; biphenyl group; It may be a terphenyl group, and the like, but is not limited thereto.
  • the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited.
  • the polycyclic aryl group includes a naphthyl group; anthracenyl group; phenanthryl group; triphenyl group; pyrenyl group; phenalenyl group; perylenyl group; chrysenyl group; It may be a fluorenyl group, but is not limited thereto.
  • the substituted aryl group may include a form in which an aliphatic ring is condensed to an aryl group.
  • a tetrahydronaphthalene group of the following structure is included in a substituted aryl group.
  • one of the carbons of the benzene ring may be connected to another position.
  • the heterocyclic group is a cyclic group including at least one of N, O, S, and Si as heteroatoms, and the number of carbon atoms is not particularly limited, but is 2 to 60, or 2 to 30.
  • the heterocyclic group include, but are not limited to, a pyridyl group; quinoline group; thiophene group; dibenzothiophene group; furan group; dibenzofuran group; naphthobenzofuran group; a carbazole group; benzocarbazole group; naphthobenzothiophene group; hexahydrocarbazole group; dihydroacridine group; dihydrodibenzoazacillin group; phenoxazine; phenothiazine; dihydrodibenzoazacillin group; spiro (dibenzosilol-dibenzoazacillin) groups; There is a spiro (acridine-
  • the hydrocarbon ring may be an aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the description of the above-described aryl group may be applied except that the aromatic hydrocarbon ring is not monovalent, and the aliphatic hydrocarbon ring is Except for the non-monovalent, the above description of the cycloalkyl group may be applied.
  • the condensed ring of the aromatic and the aliphatic include a 1,2,3,4-tetrahydronaphthalene group, a 2,3-dihydro-1H-indene group, and the like, but are not limited thereto.
  • the aromatic hydrocarbon ring refers to a ring in which pi electrons are completely conjugated and planar, and the description regarding the aryl group described above may be applied, except that it is a divalent group.
  • the aliphatic hydrocarbon ring refers to all hydrocarbon rings except for the aromatic hydrocarbon ring, and may include a cycloalkyl ring. Except that the cycloalkyl ring is a divalent group, the description of the cycloalkyl group described above may be applied.
  • the substituted aliphatic hydrocarbon ring also includes an aliphatic hydrocarbon ring in which an aromatic ring is condensed.
  • the heteroaryl group includes one or more atoms other than carbon, that is, heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se and S.
  • the number of carbon atoms is not particularly limited, but preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic.
  • heteroaryl group examples include a thiophene group; furan group; pyrrole group; imidazolyl group; thiazolyl group; oxazolyl group; oxadiazolyl group; pyridyl group; bipyridyl group; pyrimidyl group; triazinyl group; triazolyl group; acrydyl group; pyridazinyl group; pyrazinyl group; quinolinyl group; quinazolinyl group; quinoxalinyl group; phthalazinyl group; pyrido pyrimidyl group; pyrido pyrazinyl group; pyrazino pyrazinyl group; isoquinolinyl group; indolyl group; carbazolyl group; benzoxazolyl group; benzimidazolyl group; benzothiazolyl group; benzocarbazolyl group; benzothiophene
  • heterocyclic group In the present invention, the description of the above-mentioned heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • adjacent group means a substituent substituted on an atom directly connected to the atom in which the substituent is substituted, a substituent sterically closest to the substituent, or another substituent substituted on 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" groups.
  • Chemical Formula 1 is represented by any one of Chemical Formulas 2 to 5 below.
  • X, Ar, L, R1 to R5, and r1 to r5 are as defined in Formula 1 above.
  • R1 and R2 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combined with an adjacent group to form a substituted or unsubstituted ring.
  • R1 and R2 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 30 alkyl group; Alternatively, it is an aryl group having 6 to 30 carbon atoms, or combining with an adjacent group to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.
  • R1 and R2 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combining with an adjacent group to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.
  • R1 and R2 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an aryl group having 6 to 30 carbon atoms, or a ring having 2 to 30 carbon atoms by combining with an adjacent group.
  • R1 and R2 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; or a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted benzene ring by combining with an adjacent group.
  • R1 and R2 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; phenyl group; naphthyl group; anthracenyl group; or a phenanthrenyl group, or a benzene ring by combining with an adjacent group.
  • R1 and R2 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted phenyl group, or a substituted or unsubstituted benzene ring by combining with an adjacent group.
  • R1 and R2 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a phenyl group, or a benzene ring by combining with an adjacent group.
  • R1 of Formula 1 is combined with an adjacent group to form a benzene ring.
  • R2 of Formula 1 is combined with an adjacent group to form a benzene ring.
  • R3 and R4 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combined with an adjacent group to form a substituted or unsubstituted ring.
  • R3 and R4 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 30 alkyl group; Alternatively, it is an aryl group having 6 to 30 carbon atoms, or combining with an adjacent group to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.
  • R3 and R4 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combining with an adjacent group to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.
  • R3 and R4 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or an aryl group having 6 to 30 carbon atoms, or a ring having 2 to 30 carbon atoms by combining with an adjacent group.
  • R3 and R4 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; or a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted benzene ring by combining with an adjacent group.
  • R3 and R4 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; phenyl group; naphthyl group; anthracenyl group; or a phenanthrenyl group, or a benzene ring by combining with an adjacent group.
  • R3 and R4 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted phenyl group, or a substituted or unsubstituted benzene ring by combining with an adjacent group.
  • R3 and R4 in Formula 1 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a phenyl group, or a benzene ring by combining with an adjacent group.
  • R3 of Formula 1 is combined with an adjacent group to form a benzene ring.
  • R4 in Formula 1 is combined with an adjacent group to form a benzene ring.
  • R5 in Formula 1 is hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combined with an adjacent group to form a substituted or unsubstituted ring.
  • R5 in Formula 1 is hydrogen; heavy hydrogen; a substituted or unsubstituted C 1 to C 30 alkyl group; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combining with an adjacent group to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.
  • R5 in Formula 1 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combining with an adjacent group to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.
  • R5 in Formula 1 is hydrogen; heavy hydrogen; Or an aryl group having 6 to 30 carbon atoms, or a ring having 2 to 30 carbon atoms by combining with an adjacent group.
  • R5 in Formula 1 is hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; or a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted benzene ring by combining with an adjacent group.
  • R5 in Formula 1 is hydrogen; heavy hydrogen; phenyl group; naphthyl group; anthracenyl group; or a phenanthrenyl group, or a benzene ring by combining with an adjacent group.
  • R5 in Formula 1 is hydrogen; heavy hydrogen; or a substituted or unsubstituted phenyl group, or a substituted or unsubstituted benzene ring by combining with an adjacent group.
  • R5 in Formula 1 is hydrogen; heavy hydrogen; or a phenyl group, or a benzene ring by combining with an adjacent group.
  • R5 of Formula 1 is combined with an adjacent group to form a benzene ring.
  • r1 to r5 are integers of 0 to 4, respectively.
  • r1 is an integer of 0. According to another exemplary embodiment of the present invention, r1 is an integer of 1. According to another embodiment of the present invention, r1 is an integer of 2. According to another exemplary embodiment of the present invention, r1 is an integer of 3. According to another exemplary embodiment of the present invention, r1 is an integer of 4. When r1 is 2 or more, R1 in parentheses is the same as or different from each other.
  • r2 is an integer of 0. According to another exemplary embodiment of the present invention, r2 is an integer of 1. According to another embodiment of the present invention, r2 is an integer of 2. According to another exemplary embodiment of the present invention, r2 is an integer of 3. According to another exemplary embodiment of the present invention, r2 is an integer of 4. When r2 is 2 or more, R2 in parentheses is the same as or different from each other.
  • r3 is an integer of 0. According to another exemplary embodiment of the present invention, r3 is an integer of 1. According to another embodiment of the present invention, r3 is an integer of 2. According to another exemplary embodiment of the present invention, r3 is an integer of 3. According to another exemplary embodiment of the present invention, r3 is an integer of 4. When r3 is 2 or more, R3 in parentheses is the same as or different from each other.
  • r4 is an integer of 0. According to another exemplary embodiment of the present invention, r4 is an integer of 1. According to another embodiment of the present invention, r4 is an integer of 2. According to another exemplary embodiment of the present invention, r4 is an integer of 3. According to another exemplary embodiment of the present invention, r4 is an integer of 4. When r4 is 2 or more, R4 in parentheses is the same as or different from each other.
  • r5 is an integer of 0. According to another exemplary embodiment of the present invention, r5 is an integer of 1. According to another embodiment of the present invention, r5 is an integer of 2. According to another exemplary embodiment of the present invention, r5 is an integer of 3. According to another exemplary embodiment of the present invention, r5 is an integer of 4. When r5 is 2 or more, R5 in parentheses is the same as or different from each other.
  • L in Formula 1 is a direct bond; or a substituted or unsubstituted arylene group.
  • L in Formula 1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L in Formula 1 is a direct bond; or a substituted or unsubstituted C6-C20 arylene group.
  • L in Formula 1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.
  • L in Formula 1 is a direct bond; or an arylene group having 6 to 30 carbon atoms. According to another exemplary embodiment of the present invention, L in Formula 1 is a direct bond; or an arylene group having 6 to 20 carbon atoms. According to another exemplary embodiment of the present invention, L in Formula 1 is a direct bond; or an arylene group having 6 to 12 carbon atoms.
  • L in Formula 1 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted divalent biphenyl group; a substituted or unsubstituted divalent terphenyl group; a substituted or unsubstituted naphthylene group; a substituted or unsubstituted anthracenylene group; or a substituted or unsubstituted phenanthrenylene group.
  • L in Formula 1 is a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted divalent biphenyl group; or a substituted or unsubstituted naphthylene group.
  • L in Formula 1 is a direct bond; phenylene group; divalent biphenyl group; or a naphthylene group.
  • L in Formula 1 is a direct bond; or a substituted or unsubstituted phenylene group.
  • L in Formula 1 is a direct bond or a phenylene group.
  • Ar in Formula 1 is a substituted or unsubstituted alkyl group having 10 to 30 carbon atoms; a substituted or unsubstituted aryl group having 10 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 10 to 30 carbon atoms.
  • Ar in Formula 1 is a substituted or unsubstituted C10 to C20 alkyl group; a substituted or unsubstituted C10 to C20 aryl group; Or a substituted or unsubstituted heterocyclic group having 10 to 20 carbon atoms.
  • Ar in Formula 1 is a substituted or unsubstituted aryl group having 10 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 10 to 30 carbon atoms.
  • Ar in Formula 1 is a substituted or unsubstituted aryl group having 10 to 25 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 10 to 25 carbon atoms.
  • Ar in Formula 1 is a substituted or unsubstituted aryl group having 10 to 20 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 10 to 20 carbon atoms.
  • Ar of Formula 1 is an aryl group of 10 to 30; or a heterocyclic group having 10 to 30 carbon atoms.
  • Ar of Formula 1 is an aryl group of 10 to 25; or a heterocyclic group having 10 to 25 carbon atoms.
  • Ar of Formula 1 is an aryl group of 10 to 20; or a heterocyclic group having 10 to 20 carbon atoms.
  • Ar in Formula 1 is a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorene group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
  • Ar in Formula 1 is a biphenyl group; terphenyl group; naphthyl group; anthracenyl group; phenanthrenyl group; triphenylene group; fluorene group; dibenzofuran group; or a dibenzothiophene group.
  • Ar in Formula 1 is a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a naphthyl group unsubstituted or substituted with a phenyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted fluorene group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
  • Ar in Formula 1 is a biphenyl group; terphenyl group; a naphthyl group unsubstituted or substituted with a phenyl group; anthracenyl group; phenanthrenyl group; triphenylene group; fluorene group; dibenzofuran group; or a dibenzothiophene group.
  • Ar in Formula 1 is any one selected from the following group 1.
  • the structure selected from Group 1 is deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; And substituted or unsubstituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group,
  • the dotted line denotes a position bonded to N in Formula 1.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 61 to 63.
  • R61 to R63 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • r61 to r63 are each an integer of 0 to 6,
  • X, Ar, L, R1 to R4, and r1 to r4 are as defined in Formula 1 above.
  • R61 to R63 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C 1 to C 30 alkyl group; or a substituted or unsubstituted 6 to 30 aryl group.
  • R61 to R63 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C 1 to C 10 alkyl group; or a substituted or unsubstituted 6 to 20 aryl group.
  • R61 to R63 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C6-C20 aryl group.
  • R61 to R63 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.
  • R61 to R63 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; phenyl group; biphenyl group; or a naphthyl group.
  • R61 to R63 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.
  • R61 to R63 are the same as or different from each other, and each independently hydrogen; phenyl group; or a naphthyl group.
  • R61 to R63 are the same as or different from each other, and each independently represent hydrogen or deuterium.
  • R61 to R63 are each hydrogen.
  • r61 is an integer of 0. According to another exemplary embodiment of the present invention, r61 is an integer of 1. According to another embodiment of the present invention, r61 is an integer of 2. According to another exemplary embodiment of the present invention, r61 is an integer of 3. According to another exemplary embodiment of the present invention, r61 is an integer of 4. According to another exemplary embodiment of the present invention, r61 is an integer of 5. According to another exemplary embodiment of the present invention, r61 is an integer of 6. When r61 is 2 or more, R61 in parentheses is the same as or different from each other.
  • r62 is an integer of 0. According to another exemplary embodiment of the present invention, r62 is an integer of 1. According to another embodiment of the present invention, r62 is an integer of 2. According to another exemplary embodiment of the present invention, r62 is an integer of 3. According to another exemplary embodiment of the present invention, r62 is an integer of 4. According to another exemplary embodiment of the present invention, r62 is an integer of 5. According to another exemplary embodiment of the present invention, r62 is an integer of 6. When r62 is 2 or more, R62 in parentheses is the same as or different from each other.
  • r63 is an integer of 0. According to another exemplary embodiment of the present invention, r63 is an integer of 1. According to another exemplary embodiment of the present invention, r63 is an integer of 2. According to another exemplary embodiment of the present invention, r63 is an integer of 3. According to another exemplary embodiment of the present invention, r63 is an integer of 4. According to another exemplary embodiment of the present invention, r63 is an integer of 5. According to another exemplary embodiment of the present invention, r63 is an integer of 6. When r63 is 2 or more, R63 in parentheses is the same as or different from each other.
  • Chemical Formula 1 is represented by any one of Chemical Formulas 71 to 73 below.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • r11 to r13 are each an integer of 0 to 6
  • X, Ar, L, R2 to R5, and r2 to r5 are as defined in Formula 1 above.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C 1 to C 30 alkyl group; or a substituted or unsubstituted 6 to 30 aryl group.
  • R11 to 13 are hydrogen; heavy hydrogen; halogen group; cyano group; a substituted or unsubstituted C 1 to C 10 alkyl group; or a substituted or unsubstituted 6 to 20 aryl group.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; or a substituted or unsubstituted C6-C20 aryl group.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; phenyl group; biphenyl group; or a naphthyl group.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.
  • R11 to R13 are the same as or different from each other, and each independently hydrogen; phenyl group; or a naphthyl group.
  • R11 to R13 are the same as or different from each other, and each independently represent hydrogen or deuterium.
  • R11 to R13 are each hydrogen.
  • r11 is an integer of 0. According to another exemplary embodiment of the present invention, r11 is an integer of 1. According to another exemplary embodiment of the present invention, r11 is an integer of 2. According to another exemplary embodiment of the present invention, r11 is an integer of 3. According to another exemplary embodiment of the present invention, r11 is an integer of 4. According to another exemplary embodiment of the present invention, r11 is an integer of 5. According to another exemplary embodiment of the present invention, r11 is an integer of 6. When r11 is 2 or more, R11 in parentheses is the same as or different from each other.
  • r12 is an integer of 0. According to another exemplary embodiment of the present invention, r12 is an integer of 1. According to another exemplary embodiment of the present invention, r12 is an integer of 2. According to another exemplary embodiment of the present invention, r12 is an integer of 3. According to another exemplary embodiment of the present invention, r12 is an integer of 4. According to another exemplary embodiment of the present invention, r12 is an integer of 5. According to another exemplary embodiment of the present invention, r12 is an integer of 6. When r12 is 2 or more, R12 in parentheses is the same as or different from each other.
  • r13 is an integer of 0. According to another exemplary embodiment of the present invention, r13 is an integer of 1. According to another embodiment of the present invention, r13 is an integer of 2. According to another exemplary embodiment of the present invention, r13 is an integer of 3. According to another exemplary embodiment of the present invention, r13 is an integer of 4. According to another exemplary embodiment of the present invention, r13 is an integer of 5. According to another exemplary embodiment of the present invention, r13 is an integer of 6. When r13 is 2 or more, R13 in parentheses is the same as or different from each other.
  • Formula 1 is any one selected from the following compounds.
  • the compound represented by Formula 1 may be synthesized by a method known in the art or a synthesis example to be described later, and the type, position or number of substituents is based on a technique known in the art. may be changed accordingly. A specific synthesis example will be described later.
  • One embodiment of the present invention is a positive electrode; cathode; and an organic material layer provided between the anode and the cathode, wherein the organic material layer includes the compound represented by Formula 1 above.
  • the organic material layer including the compound represented by Formula 1 is a light emitting layer.
  • the organic light emitting device includes two or more organic material layers, and the two or more organic material layers include the compound represented by Formula 1 above.
  • the organic material layer of any one of the two or more organic material layers includes the compound represented by Chemical Formula 1, and further includes the remaining one or more organic material layers.
  • the remaining one or more organic material layers according to an exemplary embodiment do not include the compound represented by Formula 1 above.
  • the remaining one or more organic material layers according to another exemplary embodiment further include a compound represented by Formula 1 above.
  • the two or more organic material layers are, for example, a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, selected from the group consisting of an electron injection and transport layer, etc. It contains two or more floors.
  • the hole injection and transport layer means a layer that simultaneously injects and transports holes
  • the electron injection and transport layer means a layer that simultaneously injects and transports electrons.
  • the organic material layer constituting the group is only an example, and is not limited thereto.
  • the organic material layer included in the organic light emitting device includes two or more organic material layers, one organic material layer is a light emitting layer, and the other one or more organic material layers include the compound represented by Formula 1 above.
  • the organic material layer included in the organic light emitting device is two or more organic material layers, one organic material layer is a light emitting layer, any one organic material layer among the remaining organic material layers is an electron blocking layer, and the electron blocking layer is the and a compound represented by the formula (1).
  • the two or more organic material layers may include two or more layers performing the same role, if necessary.
  • An organic light emitting diode according to an example includes a first electron blocking layer and a second electron blocking layer. However, it is not limited to the above example.
  • the organic material layers may be formed of the same material or different materials.
  • the organic material layer includes a light emitting layer.
  • the light emitting layer includes the compound represented by Formula 1 above.
  • the light emitting layer includes the compound represented by Formula 1 as a host of the light emitting layer.
  • the light emitting layer includes the compound represented by Formula 1 as a dopant of the light emitting layer.
  • the organic material layer further includes one or more layers selected from the group consisting of an electron blocking layer, a hole blocking layer, a hole injection layer, a hole transport layer, a hole injection and transport layer.
  • the at least one layer selected from the group consisting of the electron blocking layer, the hole blocking layer, the hole injection layer, the hole transport layer, and the hole injection and transport layer includes the compound represented by Formula 1 above.
  • the organic material layer of the organic light emitting device has a single-layer structure.
  • the organic material layer having a single layer structure is provided between the anode and the cathode of the organic light emitting device, and the organic material layer includes the compound represented by Formula 1 above.
  • the organic material layer having a single-layer structure is a light emitting layer, wherein the light emitting layer includes the compound represented by Formula 1 above.
  • the organic material layer of the organic light emitting device has a multilayer structure in which two or more organic material layers are stacked.
  • the organic material layer having the multi-layer structure is provided between the anode and the cathode of the organic light emitting device.
  • the organic material layer of the multi-layer structure includes a light emitting layer and an organic material layer other than the light emitting layer.
  • the light emitting layer is provided between the anode and the cathode, and an organic material layer other than the light emitting layer is provided between the anode and the light emitting layer.
  • the light emitting layer is provided between the anode and the cathode, and an organic material layer other than the light emitting layer is provided between the light emitting layer and the cathode.
  • the light-emitting layer is provided between the anode and the cathode, any one organic material layer other than the light-emitting layer is provided between the anode and the light-emitting layer, and any one organic material layer other than the light-emitting layer is provided between the light-emitting layer and the cathode do.
  • the structure is merely an example, and is not limited thereto.
  • the organic material layer other than the light emitting layer is, for example, a hole injection and transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, selected from the group consisting of an electron injection and transport layer, etc. It may be one or more layers, but is not limited thereto.
  • a hole injection layer, a hole transport layer, or an electron blocking layer is provided between the anode and the light emitting layer.
  • the hole injection layer is provided on the anode
  • the hole transport layer is provided on the hole injection layer
  • the electron blocking layer is provided on the hole injection layer, but the example is not limited thereto.
  • an electron injection layer, an electron transport layer, or a hole blocking layer is provided between the cathode and the light emitting layer.
  • the hole blocking layer is provided on the emission layer
  • the electron transport layer is provided on the hole blocking layer
  • the electron injection layer is provided on the electron transport layer, but is not limited to the above example.
  • the organic material layer having a multilayer structure included in the organic light emitting device includes: a light emitting layer; and at least one organic material layer selected from the group consisting of a hole injection and transport layer, a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer, wherein the light emitting layer is an anode and between the cathode.
  • the at least one organic material layer is at least one of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer. More preferably, the at least one organic material layer is an electron blocking layer.
  • the organic material layer includes an electron blocking layer
  • the electron blocking layer includes the compound represented by Formula 1 above.
  • the organic material layer includes a hole injection layer.
  • the organic material layer includes a hole transport layer.
  • the organic material layer includes a hole injection and transport layer.
  • the organic material layer is a hole injection layer; hole transport layer; hole injection and transport layer; and at least one layer selected from the group consisting of an electron blocking layer.
  • the organic material layer includes a light emitting layer; and a hole injection layer; hole transport layer; hole injection and transport layer; and at least one layer selected from the group consisting of an electron blocking layer, the hole injection layer; hole transport layer; hole injection and transport layer; And at least one layer selected from the group consisting of an electron blocking layer includes the compound.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer may include the compound.
  • One embodiment of the present invention is a positive electrode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein the at least one organic material layer includes the compound represented by Formula 1 above.
  • Another embodiment of the present invention is a positive electrode; cathode; and two or more organic material layers provided between the anode and the cathode, wherein the two or more organic material layers include: a light emitting layer; and at least one of a hole injection layer, a hole transport layer, a hole injection and transport layer, and an electron blocking layer, wherein at least one of the hole injection layer, the hole transport layer, the hole injection and transport layer, and the electron blocking layer is in Formula 1 It provides an organic light emitting device comprising a compound represented by.
  • a specific embodiment of the present invention is a positive electrode; cathode; and two or more organic material layers provided between the anode and the cathode, wherein the two or more organic material layers include: a light emitting layer; and an electron blocking layer, wherein the electron blocking layer provides an organic light emitting device comprising the compound represented by Formula 1 above.
  • the organic light emitting device may have, for example, a stacked structure as follows, but is not limited thereto.
  • the structure of the organic light emitting device of the present invention may have the structure shown in FIGS. 1 and 2 , but is not limited thereto.
  • the compound of Formula 1 illustrates a structure of an organic light emitting device in which a substrate 1, an anode 2, an organic material layer 3, and a cathode 10 are sequentially stacked.
  • the compound of Formula 1 may be included in the organic material layer 3 .
  • the cathode 10 shows a substrate 1, an anode 2, a hole injection layer 4, a hole transport layer 5, an electron blocking layer 100, a light emitting layer 6, a hole blocking layer 7, an electron injection and transport layer ( 8) and the cathode 10 are sequentially stacked, the structure of the organic light emitting device is exemplified.
  • the compound of Formula 1 may be included in the electron blocking layer 100 .
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • a member when a member is said to be located "on" another member, this includes not only a case in which a member is in contact with another member but also a case in which another member is present between the two members.
  • the "layer” means compatible with the 'film' mainly used in the art, and refers to a coating covering a desired area.
  • the size of the “layers” is not limited, and each “layer” may have the same size or different sizes. In one embodiment, the size of a “layer” may be equal to the size of the entire device, may correspond to the size of a specific functional area, and may be as small as a single sub-pixel.
  • the meaning that a specific material A is included in layer B means that i) one or more types of material A are included in one layer B, and ii) layer B is composed of one or more layers, and material A is multi-layered B. It includes everything included in one or more floors among the floors.
  • the meaning that a specific material A is included in the C layer or the D layer means i) is included in one or more of the one or more layers C, ii) is included in one or more of the one or more layers D, or iii ) means all of which are included in one or more layers C and one or more layers D, respectively.
  • the light emitting layer includes a host and a dopant.
  • the host and dopant used in the light emitting layer materials known in the art may be used.
  • the dopant includes a phosphorescent dopant or a fluorescent dopant.
  • the fluorescent dopant may include an arylamine-based compound or a boron compound known in the art, but is not limited thereto.
  • the organic material layer further includes one or two or more n-type dopants selected from alkali metals and alkaline earth metals.
  • the organic alkali metal compound or the organic alkaline earth metal compound is used as the n-type dopant, it is possible to secure the stability of the hole from the light emitting layer, thereby improving the lifespan of the organic light emitting device.
  • the ratio of the organic alkali metal compound or the organic alkaline earth metal compound to the electron mobility of the electron transport layer the balance between holes and electrons in the light emitting layer can be maximized, thereby increasing luminous efficiency.
  • LiQ is more preferable as the n-type dopant used in the organic material layer in the present invention.
  • the organic light emitting device may have a tandem structure in which two or more independent devices are connected in series.
  • the tandem structure may have a form in which each organic light emitting device is bonded to a charge generating layer. Since a device having a tandem structure can be driven at a lower current than a unit device based on the same brightness, there is an advantage in that the lifespan characteristics of the device are greatly improved.
  • the organic material layer includes a first stack including one or more light emitting layers; a second stack comprising at least one light emitting layer; and one or more charge generating layers provided between the first stack and the second stack.
  • the organic material layer includes a first stack including one or more light emitting layers; a second stack comprising one or more light emitting layers; and a third stack including one or more light emitting layers, between the first stack and the second stack; and one or more charge generating layers, respectively, between the second stack and the third stack.
  • the charge generating layer means a layer in which holes and electrons are generated when a voltage is applied.
  • the charge generation layer may be an N-type charge generation layer or a P-type charge generation layer.
  • the N-type charge generation layer means a charge generation layer located closer to the anode than the P-type charge generation layer
  • the P-type charge generation layer means a charge generation layer located closer to the cathode than the N-type charge generation layer.
  • the N-type charge generation layer and the P-type charge generation layer may be provided in contact with each other, and in this case, an NP junction is formed.
  • an NP junction is formed.
  • Electrons are transported in the anode direction through the LUMO level of the N-type charge generating layer, and holes are transported in the cathode direction through the HOMO level of the P-type organic material layer.
  • the first stack, the second stack, and the third stack each include one or more light emitting layers, and further include a hole injection layer, a hole transport layer, an electron blocking layer, an electron injection layer, an electron transport layer, a hole blocking layer, a hole transport and a hole It may further include one or more layers of a layer for simultaneous injection (hole injection and transport layer), and a layer for simultaneous electron transport and electron injection (electron injection and transport layer).
  • the organic light emitting device of the present invention may be manufactured using materials and methods known in the art, except that the organic material layer includes the compound.
  • the organic light emitting diode of the present invention may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form the anode.
  • an organic material layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer or an electron injection layer thereon
  • a material that can be used as a cathode is deposited thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the manufacturing method is not limited thereto.
  • the compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
  • anode material a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer.
  • metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO 2 : a combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • metals or alloys thereof such as, for example, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; LiF/Al or a multi-layered material such as LiO 2 /Al, but is not limited thereto.
  • the emission layer may include a host material and a dopant material.
  • Examples of the host material include a condensed aromatic ring derivative or a heterocyclic compound containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like
  • heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.
  • the dopant material examples include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex.
  • the aromatic amine derivative is a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group, and includes pyrene, anthracene, chrysene, periplanthene, and the like, having an arylamine group.
  • the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine, and one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group A substituent is substituted or unsubstituted.
  • the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
  • the hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injecting material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injecting effect for the light emitting layer or the light emitting material. In addition, a material excellent in the ability to prevent movement of excitons generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. In addition, a material excellent in the ability to form a thin film is preferable. In addition, it is preferable that the 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 metal porphyrin (porphyrin), oligothiophene, arylamine-based organic material; hexanitrile hexaazatriphenylene-based organic substances; quinacridone-based organic substances; perylene-based organic substances; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer, and may have a single layer or a multilayer structure of two or more layers.
  • the hole transport material is a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer, and a material having high hole mobility is preferable. Specific examples include, but are not limited to, an arylamine-based organic material, a carbazole-based compound, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transport material is a material capable of well injecting electrons from the cathode and transferring them to the light emitting layer, and a material having high electron mobility is preferable. Specific examples include an Al complex of 8-hydroxyquinoline; complexes comprising Alq3; organic radical compounds; hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transport layer may be used with any desired cathode material, as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function, followed by a layer of aluminum or silver. Specifically, there are cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer is followed.
  • the electron injection layer is a layer that receives electrons from the electrode.
  • the electron injecting material it is preferable to have an excellent electron transporting ability, an electron receiving effect from the cathode, and an excellent electron injecting effect to the light emitting layer or the light emitting material.
  • a material that prevents excitons generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and bis(8-hydroxyquinolinato)manganese. , tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h ]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) (o-crezolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , but is not limited thereto.
  • the electron blocking layer is a layer capable of improving the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the emission layer.
  • the electron blocking layer may be formed between the emission layer and the hole injection layer or between the emission layer and a layer that simultaneously injects and transports holes.
  • the hole blocking layer is a layer that blocks the holes from reaching the cathode, and may be generally formed under the same conditions as the electron injection layer.
  • the hole blocking layer material includes, but is not limited to, an oxadiazole derivative, a triazole derivative, a phenanthroline derivative, an aluminum complex, and the like.
  • the organic light emitting device according to the present invention may be a top emission type, a back emission type, or a double side emission type depending on the material used.
  • An exemplary embodiment of the present invention provides an electronic device including an organic light emitting device including the compound of Formula 1 above.
  • the electronic device includes an interlayer insulating film of a semiconductor device, a color filter, a black matrix, an overcoat, a column spacer, a passivation film, a buffer coat film, an insulating film for a multilayer printed circuit board, a cover coat of a flexible copper clad plate, a buffer coat film, a multilayer printed circuit board Insulation film solder resist film, OLED insulation film, liquid crystal display element thin film transistor protective film, OLED diode, organic EL element electrode protective film and semiconductor protective film, OLED insulation film, LCD insulation film, semiconductor insulation film, solar module, touch panel, display It may include all display devices such as a panel, but is not limited thereto.
  • a glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • ITO indium tin oxide
  • a product manufactured by Fischer Co. was used as the detergent
  • distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water.
  • ultrasonic washing was performed for 10 minutes by repeating twice with distilled water.
  • ultrasonic washing was performed with a solvent of isopropyl alcohol, acetone, and methanol, and after drying, it was transported to a plasma cleaner.
  • the substrate was transported to a vacuum evaporator.
  • a hole injection layer was formed by thermally vacuum-depositing a compound of the following compound HI1 and a compound of the following compound HI2 to a thickness of 100 ⁇ so as to have a ratio of 98:2 (molar ratio) on the prepared anode, ITO transparent electrode.
  • a hole transport layer was formed by vacuum-depositing a compound (1150 ⁇ ) represented by the following formula HT1 on the hole injection layer.
  • compound 1 of Preparation Example 1 was vacuum-deposited to a thickness of 50 ⁇ on the hole transport layer to form an electron blocking layer.
  • the compound represented by the following formula BH and the compound represented by the following formula BD to a thickness of 200 ⁇ on the electron blocking layer were vacuum-deposited in a weight ratio of 25:1 to form a light emitting layer.
  • a hole blocking layer was formed by vacuum-depositing a compound represented by the following Chemical Formula HB1 to a film thickness of 50 ⁇ on the emission layer.
  • the compound represented by the formula ET1 and the compound represented by the formula LiQ were vacuum-deposited in a weight ratio of 1:1 to form an electron injection and transport layer to a thickness of 310 ⁇ .
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1,000 ⁇ on the electron injection and transport layer.
  • LiF lithium fluoride
  • the deposition rate of organic material was maintained at 0.4 ⁇ /sec to 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride of the negative electrode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum degree during deposition was An organic light emitting diode was manufactured by maintaining 2*10 -7 torr to 5*10 -6 torr.
  • Examples 1-2 to 1-12 an organic light emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1 of Example 1-1.
  • Comparative Examples 1-1 to 1-8 an organic light emitting diode was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1 of Example 1-1.
  • the compounds of EB1 to EB8 used in Table 1 below are as follows.
  • T95 denotes a time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
  • an organic light emitting device using a compound in which an amine group is substituted for a para moiety and a carbazole group substituted for an ortho moiety is used as an electron blocking layer according to an exemplary embodiment of the present invention. showed excellent characteristics in terms of efficiency, driving voltage, or lifespan.
  • the compound in which an aryl group is substituted with a dibenzofuran group bonded to an amine group has poor driving voltage, efficiency and stability characteristics compared to the compound according to an exemplary embodiment of the present invention.
  • the organic light emitting devices of Comparative Examples 1-1 to 1-3 using the compounds EB1 to EB3 in which a biphenyl group is substituted with a dibenzofuran group bonded to an amine group exhibit deteriorated characteristics compared to Examples such as voltage increase, efficiency decrease, and lifespan decrease. indicated.
  • the characteristics of the organic light emitting device are the dibenzofuran group and the amine group. Compared to the Example, it showed deteriorated characteristics such as voltage increase, efficiency decrease, and lifespan decrease.

Landscapes

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

Abstract

La présente invention concerne un composé représenté par la formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2021/014328 2020-10-16 2021-10-15 Composé et dispositif électroluminescent organique le comprenant WO2022080927A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202180050217.1A CN115916773A (zh) 2020-10-16 2021-10-15 化合物及包含其的有机发光器件

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR20200134252 2020-10-16
KR10-2020-0134252 2020-10-16

Publications (1)

Publication Number Publication Date
WO2022080927A1 true WO2022080927A1 (fr) 2022-04-21

Family

ID=81209135

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2021/014328 WO2022080927A1 (fr) 2020-10-16 2021-10-15 Composé et dispositif électroluminescent organique le comprenant

Country Status (3)

Country Link
KR (1) KR20220050806A (fr)
CN (1) CN115916773A (fr)
WO (1) WO2022080927A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024033884A1 (fr) * 2022-08-12 2024-02-15 호도가야 가가쿠 고교 가부시키가이샤 Composé arylamine, élément électroluminescent organique et dispositif électronique

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20220147171A (ko) * 2021-04-26 2022-11-03 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
CN116535345B (zh) * 2023-01-10 2024-03-22 江苏三月科技股份有限公司 一种芳香族胺类化合物及包含其的有机电致发光器件

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140024734A (ko) * 2012-08-21 2014-03-03 롬엔드하스전자재료코리아유한회사 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20160054855A (ko) * 2014-11-07 2016-05-17 덕산네오룩스 주식회사 유기전기소자용 조성물을 이용한 디스플레이 장치 및 유기전기소자
WO2019189033A1 (fr) * 2018-03-28 2019-10-03 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
KR20200100299A (ko) * 2019-02-18 2020-08-26 주식회사 이엘엠 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자
US20200317653A1 (en) * 2018-11-30 2020-10-08 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence device, organic electroluminescence device, and electronic device
CN113105420A (zh) * 2021-04-13 2021-07-13 浙江虹舞科技有限公司 一种稠环芳胺类化合物及其应用以及包含该化合物的有机电致发光器件

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100430549B1 (ko) 1999-01-27 2004-05-10 주식회사 엘지화학 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자 및 그의 제조 방법

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20140024734A (ko) * 2012-08-21 2014-03-03 롬엔드하스전자재료코리아유한회사 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20160054855A (ko) * 2014-11-07 2016-05-17 덕산네오룩스 주식회사 유기전기소자용 조성물을 이용한 디스플레이 장치 및 유기전기소자
WO2019189033A1 (fr) * 2018-03-28 2019-10-03 出光興産株式会社 Composé, matériau pour éléments électroluminescents organiques, élément électroluminescent organique et dispositif électronique
US20200317653A1 (en) * 2018-11-30 2020-10-08 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence device, organic electroluminescence device, and electronic device
KR20200100299A (ko) * 2019-02-18 2020-08-26 주식회사 이엘엠 유기 전기 발광 조성물 및 이를 포함하는 유기 전기 발광 소자
CN113105420A (zh) * 2021-04-13 2021-07-13 浙江虹舞科技有限公司 一种稠环芳胺类化合物及其应用以及包含该化合物的有机电致发光器件

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024033884A1 (fr) * 2022-08-12 2024-02-15 호도가야 가가쿠 고교 가부시키가이샤 Composé arylamine, élément électroluminescent organique et dispositif électronique

Also Published As

Publication number Publication date
KR20220050806A (ko) 2022-04-25
CN115916773A (zh) 2023-04-04

Similar Documents

Publication Publication Date Title
WO2017204594A1 (fr) Elément électroluminescent organique
WO2019083327A2 (fr) Dispositif électroluminescent organique utilisant un composé hétérocyclique
WO2019143151A1 (fr) Diode électroluminescente organique
WO2020145725A1 (fr) Composé et élément électroluminescent organique le comprenant
WO2021054714A1 (fr) Composé hétérocyclique et dispositif électroluminescent organique le comprenant
WO2020091521A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2019151733A1 (fr) Diode électroluminescente organique
WO2022080927A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2019182402A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2019147077A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2017146522A1 (fr) Composé hétérocyclique et diode électroluminescente organique contenant ce composé
WO2021125813A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2021091165A1 (fr) Dispositif électroluminescent organique
WO2019004791A1 (fr) Composé hétérocyclique et élément électroluminescent organique le comprenant
WO2020262861A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2020231242A1 (fr) Élément électroluminescent organique
WO2021150080A1 (fr) Composé dérivé polycyclique aromatique et dispositif électroluminescent organique l'utilisant
WO2023096405A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2022108258A1 (fr) Composé et dispositif électroluminescent organique le comprenant
WO2022031020A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2022059923A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant
WO2021034156A1 (fr) Nouveau composé et dispositif électroluminescent organique l'utilisant
WO2020246835A1 (fr) Nouveau composé et dispositif électroluminescent organique faisant appel à celui-ci
WO2020185026A1 (fr) Composé et diode électroluminescente organique le comprenant
WO2020246837A1 (fr) Nouveau composé et dispositif électroluminescent organique le comprenant

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: 21880574

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: 21880574

Country of ref document: EP

Kind code of ref document: A1