WO2022080927A1 - Compound and organic light-emitting device comprising same - Google Patents

Compound and organic light-emitting device comprising same Download PDF

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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
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Korean (ko)
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조우진
차용범
홍성길
김동헌
이성재
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주식회사 엘지화학
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Priority to CN202180050217.1A priority Critical patent/CN115916773A/en
Publication of WO2022080927A1 publication Critical patent/WO2022080927A1/en

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    • 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
    • H10K50/00—Organic light-emitting devices
    • 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
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K99/00—Subject matter not provided for in other groups of this subclass

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.

Abstract

The present invention relates to a compound represented by chemical formula 1 and an organic light-emitting device comprising same.

Description

화합물 및 이를 포함하는 유기 발광 소자Compound and organic light emitting device comprising same
본 발명은 2020년 10월 16일 한국 특허청에 제출된 한국 특허 제10-2020-0134252호의 출원일의 이익을 주장하며, 그 내용 전부는 본 발명에 포함된다.The present invention claims the benefit of the filing date of Korean Patent No. 10-2020-0134252 filed with the Korean Intellectual Property Office on October 16, 2020, the entire contents of which are incorporated herein by reference.
본 발명은 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present invention relates to a compound and an organic light emitting device comprising the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공 주입층, 정공 수송층, 전자 차단층, 발광층, 전자 수송층, 전자 주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다.In general, 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. Here, 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. can get When a voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer from the anode and electrons from the cathode are injected into the organic material layer. When the injected holes and electrons meet, excitons are formed, and these excitons are When it falls back to the ground state, it lights up.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.The development of new materials for the organic light emitting device as described above is continuously required.
(특허문헌 1) 한국 특허공개공보 제10-2000-0051826호(Patent Document 1) Korean Patent Publication No. 10-2000-0051826
본 발명은 화합물 및/또는 이를 포함하는 유기 발광 소자를 제공하고자 한다.An object of the present invention is to provide a compound and/or an organic light emitting device comprising the same.
본 발명의 일 실시상태는 하기 화학식 1로 표시되는 화합물을 제공한다.An exemplary embodiment of the present invention provides a compound represented by the following formula (1).
[화학식 1][Formula 1]
Figure PCTKR2021014328-appb-img-000001
Figure PCTKR2021014328-appb-img-000001
상기 화학식 1에 있어서,In Formula 1,
X는 O 또는 S이고,X is O or S;
Ar은 치환 또는 비치환된 탄소수 10 내지 30의 알킬기; 치환 또는 비치환된 탄소수 10 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 10 내지 30의 헤테로고리기이고,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,
L은 직접결합; 또는 치환 또는 비치환된 아릴렌기이고, L is a direct bond; Or a substituted or unsubstituted arylene group,
R1 내지 R5는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,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 내지 r5는 각각 0 내지 4의 정수이고,r1 to r5 are each an integer of 0 to 4,
r1 내지 r5가 2 이상인 경우, 괄호 안의 치환기는 서로 같거나 상이하다.When r1 to r5 are 2 or more, the substituents in parentheses are the same as or different from each other.
또한, 본 발명의 다른 일 실시상태는 양극; 음극; 및 상기 양극 및 상기 음극 사이에 구비된 유기물층을 포함하고, 상기 유기물층은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자를 제공한다.In addition, 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.
본 발명의 일 실시상태에 따른 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있다.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.
본 발명의 일 실시상태에 따른 화합물은 유기 발광 소자의 전자 차단층 재료로 사용될 수 있다.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.
본 발명의 일 실시상태에 따른 화합물은 유기 발광 소자에 포함되어 낮은 구동전압, 우수한 효율 특성, 또는 우수한 수명 특성을 갖게 하는 등 소자 특성을 향상시킬 수 있다.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.
도 1은 본 발명의 일 실시상태에 따른 유기 발광 소자를 도시한 것이다.1 illustrates an organic light emitting diode according to an exemplary embodiment of the present invention.
도 2는 본 발명의 다른 일 실시상태에 따른 유기 발광 소자를 도시한 것이다.2 illustrates an organic light emitting device according to another exemplary embodiment of the present invention.
[부호의 설명][Explanation of code]
1: 기판1: Substrate
2: 양극2: Anode
3: 유기물층3: organic layer
4: 정공 주입층4: hole injection layer
5: 정공 수송층5: hole transport layer
6: 발광층6: light emitting layer
7: 정공 차단층7: hole blocking layer
8: 전자 주입 및 수송층8: electron injection and transport layer
10: 음극10: cathode
100: 전자 차단층100: electron blocking layer
이하, 본 발명에 대하여 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명의 일 실시상태는 하기 화학식 1로 표시되는 화합물을 제공한다.An exemplary embodiment of the present invention provides a compound represented by the following formula (1).
[화학식 1][Formula 1]
Figure PCTKR2021014328-appb-img-000002
Figure PCTKR2021014328-appb-img-000002
상기 화학식 1에 있어서,In Formula 1,
X는 O 또는 S이고,X is O or S;
Ar은 치환 또는 비치환된 탄소수 10 내지 30의 알킬기; 치환 또는 비치환된 탄소수 10 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 10 내지 30의 헤테로고리기이고,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,
L은 직접결합; 또는 치환 또는 비치환된 아릴렌기이고, L is a direct bond; Or a substituted or unsubstituted arylene group,
R1 내지 R5는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,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 내지 r5는 각각 0 내지 4의 정수이고,r1 to r5 are each an integer of 0 to 4,
r1 내지 r5가 2 이상인 경우, 괄호 안의 치환기는 서로 같거나 상이하다.When r1 to r5 are 2 or more, the substituents in parentheses are the same as or different from each other.
본 발명의 일 실시상태는 상기 화학식 1로 표시되는 화합물을 제공한다.An exemplary embodiment of the present invention provides a compound represented by Formula 1 above.
본 발명의 화학식 1은 바이페닐기의 파라(para) 부분에 아민기가 결합되고, 오르토(ortho) 부분에 카바졸기가 직접결합 또는 연결기(L)를 통하여 결합되어, HOMO (highest occupied molecular orbital) 값을 높게 유지할 수 있어서, 인접한 발광층과의 에너지 장벽(energy barrier)을 감소시켜서, 전하 균형(charge balance)을 적절히 유지할 수 있다. 또한, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층이 전자 차단층으로서 사용될 경우, 생성된 엑시톤이 발광층 내에 가두어져 발광 누수가 방지되므로, 우수한 발광 효율을 갖는 유기 발광 소자를 구현할 수 있는 효과가 있다. 결과적으로, 상기 화학식 1의 화합물을 전자 차단층에 사용하는 경우, 유기 발광 소자의 장수명, 저전압 또는 고효율의 특성이 강화된다.In Chemical Formula 1 of the present invention, 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. In addition, when 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. . As a result, when 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.
본 발명에 있어서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of substituents in the present invention are described below, but are not limited thereto.
상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치, 즉 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 같거나 상이할 수 있다.The term "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.
본 발명에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 아릴기로 치환된 아릴기, 아릴기로 치환된 헤테로고리기, 알킬기로 치환된 아릴기 등일 수 있다.In the present invention, the term "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. For example, 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.
본 발명에 있어서, "인접한 기가 결합하여 형성된 고리"는 탄화수소 고리; 또는 헤테로고리를 의미한다.In the present invention, "a ring formed by bonding adjacent groups" is a hydrocarbon ring; or a heterocyclic ring.
본 발명에 있어서, 할로겐기는 F, Cl, Br, I 등이 될 수 있다. In the present invention, the halogen group may be F, Cl, Br, I, or the like.
본 발명에 있어서, 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 30인 것이 바람직하다. 구체적으로 탄소수 1 내지 20인 것이 바람직하다. 더 구체적으로는 탄소수 1 내지 10인 것이 바람직하다. 구체적인 예로는 메틸기; 에틸기; 프로필기; n-프로필기; 이소프로필기; 부틸기; n-부틸기; 이소부틸기; tert-부틸기(이하, 터부틸기라 한다); sec-부틸기; 1-메틸부틸기; 1-에틸부틸기; 펜틸기; n-펜틸기; 이소펜틸기; 네오펜틸기; tert-펜틸기; 헥실기; n-헥실기; 1-메틸펜틸기; 2-메틸펜틸기; 4-메틸-2-펜틸기; 3,3-디메틸부틸기; 2-에틸부틸기; 헵틸기; n-헵틸기; 1-메틸헥실기; 시클로펜틸메틸기; 시클로헥실메틸기; 옥틸기; n-옥틸기; tert-옥틸기; 1-메틸헵틸기; 2-에틸헥실기; 2-프로필펜틸기; n-노닐기; 2,2-디메틸헵틸기; 1-에틸프로필기; 1,1-디메틸프로필기; 이소헥실기; 2-메틸펜틸기; 4-메틸헥실기; 5-메틸헥실기 등이 있으나, 이에 한정되는 것은 아니다.In the present invention, 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. Specific examples include 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; octyl group; n-octyl group; tert-octyl group; 1-methylheptyl group; 2-ethylhexyl group; 2-propylpentyl group; n-nonyl group; 2,2-dimethylheptyl group; 1-ethylpropyl group; 1,1-dimethylpropyl group; isohexyl group; 2-methylpentyl group; 4-methylhexyl group; 5-methylhexyl group, and the like, but is not limited thereto.
본 발명에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 30인 것이 바람직하며, 탄소수 3 내지 20인 것이 더 바람직하다. 구체적으로 시클로프로필기; 시클로부틸기; 시클로펜틸기; 3-메틸시클로펜틸기; 2,3-디메틸시클로펜틸기; 시클로헥실기; 3-메틸시클로헥실기; 4-메틸시클로헥실기; 2,3-디메틸시클로헥실기; 3,4,5-트리메틸시클로헥실기; 4-tert-부틸시클로헥실기; 시클로헵틸기; 시클로옥틸기 등이 있으나, 이에 한정되는 것은 아니다.In the present invention, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, more preferably 3 to 20 carbon atoms. Specifically, a cyclopropyl group; cyclobutyl group; cyclopentyl group; 3-methylcyclopentyl group; 2,3-dimethylcyclopentyl group; cyclohexyl group; 3-methylcyclohexyl group; 4-methylcyclohexyl group; 2,3-dimethylcyclohexyl group; 3,4,5-trimethylcyclohexyl group; 4-tert-butylcyclohexyl group; cycloheptyl group; There is a cyclooctyl group, and the like, but is not limited thereto.
본 발명에 있어서, 실릴기는 ―SiRaRbRc의 화학식으로 표시될 수 있고, 상기 Ra, Rb 및 Rc는 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 실릴기는 구체적으로 트리메틸실릴기; 트리에틸실릴기; t-부틸디메틸실릴기; 비닐디메틸실릴기; 프로필디메틸실릴기; 트리페닐실릴기; 디페닐실릴기; 페닐실릴기 등이 있으나, 이에 한정되는 것은 아니다.In the present invention, 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.
본 발명에 있어서, 아민기는 -NRdRe로 나타낼 수 있으며, 상기 Rd 및 Re는 서로 같거나 상이하고, 각각 독립적으로 수소, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 아릴기, 또는 치환 또는 비치환된 헤테로아릴기일 수 있으나, 이에 한정되지 않는다. 상기 아민기는 결합되는 치환기(Rd, Re)의 종류에 따라, 알킬아민기, 알킬아릴아민기, 아릴아민기, 헤테로아릴아민기, 알킬헤테로아릴아민기, 및 아릴헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있다.In the present invention, 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. can be
본 발명에 있어서, 아릴기는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하며, 탄소수 6 내지 20인 것이 더 바람직하다. 상기 아릴기는 단환식 또는 다환식일 수 있다. 상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하다. 더 구체적으로는 탄소수 6 내지 20인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기; 바이페닐기; 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 30인 것이 바람직하고 더 구체적으로 탄소수 10 내지 20인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기; 안트라세닐기; 페난트릴기; 트리페닐기; 파이레닐기; 페날레닐기; 페릴레닐기; 크라이세닐기; 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. In the present invention, 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. When 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. Specifically, the monocyclic aryl group includes a phenyl group; biphenyl group; It may be a terphenyl group, and the like, but is not limited thereto. When the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable that it has 10 to 30 carbon atoms, and more specifically, it is preferable that it has 10 to 20 carbon atoms. Specifically, 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.
본 발명에 있어서, 치환된 아릴기는 아릴기에 지방족 고리가 축합된 형태도 포함할 수 있다. 예컨대, 하기 구조의 테트라하이드로나프탈렌기는 치환된 아릴기에 포함된다. 하기 구조에서, 벤젠고리의 탄소 중 하나가 다른 위치에 연결될 수 있다.In the present invention, the substituted aryl group may include a form in which an aliphatic ring is condensed to an aryl group. For example, a tetrahydronaphthalene group of the following structure is included in a substituted aryl group. In the following structure, one of the carbons of the benzene ring may be connected to another position.
Figure PCTKR2021014328-appb-img-000003
Figure PCTKR2021014328-appb-img-000003
본 발명에 있어서, 헤테로고리기는 이종원자로 N, O, S, 및 Si중 1개 이상을 포함하는 고리기로서, 탄소수는 특별히 한정되지 않으나 2 내지 60, 또는 2 내지 30이다. 상기 헤테로고리기의 예로는 예로는 피리딜기; 퀴놀린기; 티오펜기; 디벤조티오펜기; 퓨란기; 디벤조퓨란기; 나프토벤조퓨란기; 카바졸기; 벤조카바졸기; 나프토벤조티오펜기; 헥사하이드로카바졸기; 디하이드로아크리딘기; 디하이드로디벤조아자실린기; 페녹사진기(phenoxazine); 페노싸이아진기(phenothiazine); 디하이드로디벤조아자실린기; 스피로(디벤조실롤-디벤조아자실린)기; 스피로(아크리딘-플루오렌)기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present invention, 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. Examples of 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-fluorene) group, and the like, but is not limited thereto.
본 발명에 있어서, 탄화수소 고리는 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 상기 방향족 탄화수소 고리는 1가가 아닌 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있고, 상기 지방족 탄화수소고리는 1가가 아닌 것을 제외하고는 전술한 시클로알킬기에 관한 설명이 적용될 수 있다. 방향족과 지방족의 축합고리의 예로서 1,2,3,4-테트라하이드로나프탈렌기, 2,3-디하이드로-1H-인덴기 등을 들 수 있지만 이에 한정되는 것은 아니다. In the present invention, 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. Examples of 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.
본 발명에 있어서, 방향족 탄화수소 고리는 pi 전자가 완전히 컨쥬게이션되고 평면인 고리를 의미하는 것으로, 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present invention, 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.
본 발명에 있어서, 지방족 탄화수소 고리는 방향족 탄화수소고리를 제외한 모든 탄화수소고리를 의미하는 것으로, 시클로알킬고리를 포함할 수 있다. 시클로알킬고리는 2가기인 것을 제외하고는 전술한 시클로알킬기에 관한 설명이 적용될 수 있다. 치환된 지방족 탄화수소 고리에는 방향족 고리가 축합된 지방족 탄화수소 고리도 포함된다.In the present invention, 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.
본 발명에 있어서, 아릴렌기는 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present invention, the description of the above-described aryl group may be applied, except that the arylene group is a divalent group.
본 발명에 있어서, 헤테로아릴기는 탄소가 아닌 원자, 즉 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 30인 것이 바람직하며, 탄소수 2 내지 20인 것이 더 바람직하고, 상기 헤테로아릴기는 단환식 또는 다환식일 수 있다. 헤테로아릴기의 예로는 티오펜기; 퓨란기; 피롤기; 이미다졸릴기; 티아졸릴기; 옥사졸릴기; 옥사디아졸릴기; 피리딜기; 바이피리딜기; 피리미딜기; 트리아지닐기; 트리아졸릴기; 아크리딜기; 피리다지닐기; 피라지닐기; 퀴놀리닐기; 퀴나졸리닐기; 퀴녹살리닐기; 프탈라지닐기; 피리도 피리미딜기; 피리도 피라지닐기; 피라지노 피라지닐기; 이소퀴놀리닐기; 인돌릴기; 카바졸릴기; 벤즈옥사졸릴기; 벤즈이미다졸릴기; 벤조티아졸릴기; 벤조카바졸릴기; 벤조티오펜기; 디벤조티오펜기; 벤조퓨란기; 페난쓰롤리닐기(phenanthroline); 이소옥사졸릴기; 티아디아졸릴기; 페노티아지닐기 및 디벤조퓨란기 등이 있으나, 이에 한정되는 것은 아니다.In the present invention, 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. Examples of the heteroaryl group 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 group; dibenzothiophene group; benzofuran group; a phenanthroline group; isoxazolyl group; thiadiazolyl group; There is a phenothiazinyl group and a dibenzofuran group, but is not limited thereto.
본 발명에 있어서, 헤테로아릴기는 방향족인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present invention, the description of the above-mentioned heterocyclic group may be applied except that the heteroaryl group is aromatic.
본 발명에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오르토(ortho) 위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한" 기로 해석될 수 있다.In the present invention, "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. can For example, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 2 내지 5 중어느 하나로 표시된다.According to an exemplary embodiment of the present invention, Chemical Formula 1 is represented by any one of Chemical Formulas 2 to 5 below.
[화학식 2][Formula 2]
Figure PCTKR2021014328-appb-img-000004
Figure PCTKR2021014328-appb-img-000004
[화학식 3][Formula 3]
Figure PCTKR2021014328-appb-img-000005
Figure PCTKR2021014328-appb-img-000005
[화학식 4][Formula 4]
Figure PCTKR2021014328-appb-img-000006
Figure PCTKR2021014328-appb-img-000006
[화학식 5][Formula 5]
Figure PCTKR2021014328-appb-img-000007
Figure PCTKR2021014328-appb-img-000007
상기 화학식 2 내지 5에 있어서, X, Ar, L, R1 내지 R5, 및 r1 내지 r5는 상기 화학식 1에서 정의한 바와 같다.In Formulas 2 to 5, X, Ar, L, R1 to R5, and r1 to r5 are as defined in Formula 1 above.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 또는 탄소수 6 내지 30의 아릴기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 2 내지 30의 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 2 내지 30의 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 탄소수 6 내지 30의 아릴기이거나, 또는 인접한 기와 서로 결합하여 탄소수 2 내지 30의 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라세닐기; 또는 치환 또는 비치환된 페난트레닐기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 페닐기; 나프틸기; 안트라세닐기; 또는 페난트레닐기이거나, 또는 인접한 기와 서로 결합하여 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 페닐기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 페닐기이거나, 또는 인접한 기와 서로 결합하여 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R1은 인접한 기와 서로 결합하여 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, R1 of Formula 1 is combined with an adjacent group to form a benzene ring.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R2는 인접한 기와 서로 결합하여 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, R2 of Formula 1 is combined with an adjacent group to form a benzene ring.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R3 및 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R3 및 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 또는 탄소수 6 내지 30의 아릴기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 2 내지 30의 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R3 및 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 2 내지 30의 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R3 및 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 탄소수 6 내지 30의 아릴기이거나, 또는 인접한 기와 서로 결합하여 탄소수 2 내지 30의 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R3 및 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라세닐기; 또는 치환 또는 비치환된 페난트레닐기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R3 및 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 페닐기; 나프틸기; 안트라세닐기; 또는 페난트레닐기이거나, 또는 인접한 기와 서로 결합하여 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R3 및 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 페닐기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R3 및 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 페닐기이거나, 또는 인접한 기와 서로 결합하여 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R3은 인접한 기와 서로 결합하여 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, R3 of Formula 1 is combined with an adjacent group to form a benzene ring.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R4는 인접한 기와 서로 결합하여 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, R4 in Formula 1 is combined with an adjacent group to form a benzene ring.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R5는 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R5는 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 2 내지 30의 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R5는 수소; 중수소; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 2 내지 30의 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R5는 수소; 중수소; 또는 탄소수 6 내지 30의 아릴기이거나, 또는 인접한 기와 서로 결합하여 탄소수 2 내지 30의 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R5는 수소; 중수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라세닐기; 또는 치환 또는 비치환된 페난트레닐기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R5는 수소; 중수소; 페닐기; 나프틸기; 안트라세닐기; 또는 페난트레닐기이거나, 또는 인접한 기와 서로 결합하여 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R5는 수소; 중수소; 또는 치환 또는 비치환된 페닐기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R5는 수소; 중수소; 또는 페닐기이거나, 또는 인접한 기와 서로 결합하여 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, R5 in Formula 1 is hydrogen; heavy hydrogen; or a phenyl group, or a benzene ring by combining with an adjacent group.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 R5는 인접한 기와 서로 결합하여 벤젠 고리를 형성한다.According to an exemplary embodiment of the present invention, R5 of Formula 1 is combined with an adjacent group to form a benzene ring.
본 발명의 일 실시상태에 따르면, r1 내지 r5는 각각 0 내지 4의 정수이다.According to an exemplary embodiment of the present invention, r1 to r5 are integers of 0 to 4, respectively.
본 발명의 일 실시상태에 따르면, r1은 0의 정수이다. 본 발명의 다른 일 실시상태에 따르면, r1은 1의 정수이다. 본 발명의 또 다른 실시상태에 따르면, r1은 2의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r1은 3의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r1은 4의 정수이다. r1이 2 이상인 경우, 괄호 안의 R1은 서로 같거나 상이하다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, r2는 0의 정수이다. 본 발명의 다른 일 실시상태에 따르면, r2는 1의 정수이다. 본 발명의 또 다른 실시상태에 따르면, r2는 2의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r2는 3의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r2는 4의 정수이다. r2가 2 이상인 경우, 괄호 안의 R2는 서로 같거나 상이하다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, r3은 0의 정수이다. 본 발명의 다른 일 실시상태에 따르면, r3은 1의 정수이다. 본 발명의 또 다른 실시상태에 따르면, r3은 2의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r3은 3의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r3은 4의 정수이다. r3이 2 이상인 경우, 괄호 안의 R3은 서로 같거나 상이하다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, r4는 0의 정수이다. 본 발명의 다른 일 실시상태에 따르면, r4는 1의 정수이다. 본 발명의 또 다른 실시상태에 따르면, r4는 2의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r4는 3의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r4는 4의 정수이다. r4가 2 이상인 경우, 괄호 안의 R4는 서로 같거나 상이하다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, r5는 0의 정수이다. 본 발명의 다른 일 실시상태에 따르면, r5는 1의 정수이다. 본 발명의 또 다른 실시상태에 따르면, r5는 2의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r5는 3의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r5는 4의 정수이다. r5가 2 이상인 경우, 괄호 안의 R5는 서로 같거나 상이하다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 L은 직접결합; 또는 치환 또는 비치환된 아릴렌기이다.According to an exemplary embodiment of the present invention, L in Formula 1 is a direct bond; or a substituted or unsubstituted arylene group.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 L은 직접결합; 또는 치환 또는 비치환된 탄소수 6 내지 30의 아릴렌기이다. 본 발명의 다른 일 실시상태에 따르면, 상기 화학식 1의 L은 직접결합; 또는 치환 또는 비치환된 탄소수 6 내지 20의 아릴렌기이다. 본 발명의 또 다른 일 실시상태에 따르면, 상기 화학식 1의 L은 직접결합; 또는 치환 또는 비치환된 탄소수 6 내지 12의 아릴렌기이다.According to an exemplary embodiment of the present invention, L in Formula 1 is a direct bond; or a substituted or unsubstituted 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 a substituted or unsubstituted C6-C20 arylene group. According to another exemplary embodiment of the present invention, L in Formula 1 is a direct bond; or a substituted or unsubstituted arylene group having 6 to 12 carbon atoms.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 L은 직접결합; 또는 탄소수 6 내지 30의 아릴렌기이다. 본 발명의 다른 일 실시상태에 따르면, 상기 화학식 1의 L은 직접결합; 또는 탄소수 6 내지 20의 아릴렌기이다. 본 발명의 또 다른 일 실시상태에 따르면, 상기 화학식 1의 L은 직접결합; 또는 탄소수 6 내지 12의 아릴렌기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 L은 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 2가의 바이페닐기; 치환 또는 비치환된 2가의 터페닐기; 치환 또는 비치환된 나프틸렌기; 치환 또는 비치환된 안트라세닐렌기; 또는 치환 또는 비치환된 페난트레닐렌기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 L은 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 2가의 바이페닐기; 또는 치환 또는 비치환된 나프틸렌기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 L은 직접결합; 페닐렌기; 2가의 바이페닐기; 또는 나프틸렌기이다.According to an exemplary embodiment of the present invention, L in Formula 1 is a direct bond; phenylene group; divalent biphenyl group; or a naphthylene group.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 L은 직접결합; 또는 치환 또는 비치환된 페닐렌기이다.According to an exemplary embodiment of the present invention, L in Formula 1 is a direct bond; or a substituted or unsubstituted phenylene group.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 L은 직접결합 또는 페닐렌기이다.According to an exemplary embodiment of the present invention, L in Formula 1 is a direct bond or a phenylene group.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 Ar은 탄소수 10 내지 30의 치환 또는 비치환된 알킬기; 치환 또는 비치환된 탄소수 10 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 10 내지 30의 헤테로고리기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 다른 일 실시상태에 따르면, 상기 화학식 1의 Ar은 치환 또는 비치환된 탄소수 10 내지 20의 알킬기; 치환 또는 비치환된 탄소수 10 내지 20의 아릴기; 또는 치환 또는 비치환된 탄소수 10 내지 20의 헤테로고리기이다.According to another exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 Ar은 치환 또는 비치환된 탄소수 10 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 10 내지 30의 헤테로고리기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 Ar은 치환 또는 비치환된 탄소수 10 내지 25의 아릴기; 또는 치환 또는 비치환된 탄소수 10 내지 25의 헤테로고리기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 Ar은 치환 또는 비치환된 탄소수 10 내지 20의 아릴기; 또는 치환 또는 비치환된 탄소수 10 내지 20의 헤테로고리기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 Ar은 10 내지 30의 아릴기; 또는 탄소수 10 내지 30의 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar of Formula 1 is an aryl group of 10 to 30; or a heterocyclic group having 10 to 30 carbon atoms.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 Ar은 10 내지 25의 아릴기; 또는 탄소수 10 내지 25의 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar of Formula 1 is an aryl group of 10 to 25; or a heterocyclic group having 10 to 25 carbon atoms.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 Ar은 10 내지 20의 아릴기; 또는 탄소수 10 내지 20의 헤테로고리기이다.According to an exemplary embodiment of the present invention, Ar of Formula 1 is an aryl group of 10 to 20; or a heterocyclic group having 10 to 20 carbon atoms.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 Ar은 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라세닐기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 플루오렌기; 치환 또는 비치환된 디벤조퓨란기; 또는 치환 또는 비치환된 디벤조티오펜기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 Ar은 바이페닐기; 터페닐기; 나프틸기; 안트라세닐기; 페난트레닐기; 트리페닐렌기; 플루오렌기; 디벤조퓨란기; 또는 디벤조티오펜기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 Ar은 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 페닐기로 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라세닐기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 트리페닐렌기; 치환 또는 비치환된 플루오렌기; 치환 또는 비치환된 디벤조퓨란기; 또는 치환 또는 비치환된 디벤조티오펜기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 Ar은 바이페닐기; 터페닐기; 페닐기로 치환 또는 비치환된 나프틸기; 안트라세닐기; 페난트레닐기; 트리페닐렌기; 플루오렌기; 디벤조퓨란기; 또는 디벤조티오펜기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1의 Ar은 하기 그룹 1에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present invention, Ar in Formula 1 is any one selected from the following group 1.
[그룹 1][Group 1]
Figure PCTKR2021014328-appb-img-000008
Figure PCTKR2021014328-appb-img-000008
상기 그룹 1에서 선택된 구조는 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환 또는 비치환되고,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,
상기 구조에서 점선은 화학식 1의 N에 결합하는 위치를 의미한다.In the structure, the dotted line denotes a position bonded to N in Formula 1.
본 발명의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 61 내지 63 중 어느 하나로 표시된다.According to an exemplary embodiment of the present invention, Chemical Formula 1 is represented by any one of the following Chemical Formulas 61 to 63.
[화학식 61][Formula 61]
Figure PCTKR2021014328-appb-img-000009
Figure PCTKR2021014328-appb-img-000009
[화학식 62][Formula 62]
Figure PCTKR2021014328-appb-img-000010
Figure PCTKR2021014328-appb-img-000010
[화학식 63][Formula 63]
Figure PCTKR2021014328-appb-img-000011
Figure PCTKR2021014328-appb-img-000011
상기 화학식 61 내지 63에 있어서, In Formulas 61 to 63,
R61 내지 R63은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이고,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 내지 r63은 각각 0 내지 6의 정수이고,r61 to r63 are each an integer of 0 to 6,
r61 내지 r63이 2 이상인 경우, 괄호 안의 치환기는 서로 같거나 상이하고,When r61 to r63 are 2 or more, the substituents in parentheses are the same as or different from each other,
X, Ar, L, R1 내지 R4, 및 r1 내지 r4는 상기 화학식 1에서 정의한 바와 같다.X, Ar, L, R1 to R4, and r1 to r4 are as defined in Formula 1 above.
본 발명의 일 실시상태에 따르면, 상기 R61 내지 R63은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 또는 치환 또는 비치환된 6 내지 30의 아릴기이다. 본 발명의 다른 실시상태에 따르면, 상기 R61 내지 R63은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 또는 치환 또는 비치환된 6 내지 20의 아릴기이다.According to an exemplary embodiment of the present invention, 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. According to another exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 R61 내지 R63은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 R61 내지 R63은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 또는 치환 또는 비치환된 나프틸기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 R61 내지 R63은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 페닐기; 바이페닐기; 또는 나프틸기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 R61 내지 R63은 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 페닐기; 또는 치환 또는 비치환된 나프틸기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 R61 내지 R63은 서로 같거나 상이하고, 각각 독립적으로 수소; 페닐기; 또는 나프틸기이다.According to an exemplary embodiment of the present invention, R61 to R63 are the same as or different from each other, and each independently hydrogen; phenyl group; or a naphthyl group.
본 발명의 일 실시상태에 따르면, 상기 R61 내지 R63은 서로 같거나 상이하고, 각각 독립적으로 수소 또는 중수소이다.According to an exemplary embodiment of the present invention, R61 to R63 are the same as or different from each other, and each independently represent hydrogen or deuterium.
본 발명의 일 실시상태에 따르면, 상기 R61 내지 R63은 각각 수소이다.According to an exemplary embodiment of the present invention, R61 to R63 are each hydrogen.
본 발명의 일 실시상태에 따르면, r61은 0의 정수이다. 본 발명의 다른 일 실시상태에 따르면, r61은 1의 정수이다. 본 발명의 또 다른 실시상태에 따르면, r61은 2의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r61은 3의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r61은 4의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r61은 5의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r61은 6의 정수이다. r61이 2 이상인 경우, 괄호 안의 R61은 서로 같거나 상이하다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, r62는 0의 정수이다. 본 발명의 다른 일 실시상태에 따르면, r62는 1의 정수이다. 본 발명의 또 다른 실시상태에 따르면, r62는 2의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r62는 3의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r62는 4의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r62는 5의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r62는 6의 정수이다. r62가 2 이상인 경우, 괄호 안의 R62는 서로 같거나 상이하다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, r63은 0의 정수이다. 본 발명의 다른 일 실시상태에 따르면, r63은 1의 정수이다. 본 발명의 또 다른 실시상태에 따르면, r63은 2의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r63은 3의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r63은 4의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r63은 5의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r63은 6의 정수이다. r63이 2 이상인 경우, 괄호 안의 R63은 서로 같거나 상이하다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 71 내지 73 중 어느 하나로 표시된다.According to an exemplary embodiment of the present invention, Chemical Formula 1 is represented by any one of Chemical Formulas 71 to 73 below.
[화학식 71][Formula 71]
Figure PCTKR2021014328-appb-img-000012
Figure PCTKR2021014328-appb-img-000012
[화학식 72][Formula 72]
Figure PCTKR2021014328-appb-img-000013
Figure PCTKR2021014328-appb-img-000013
[화학식 73][Formula 73]
Figure PCTKR2021014328-appb-img-000014
Figure PCTKR2021014328-appb-img-000014
상기 화학식 71 내지 73에 있어서, In Formulas 71 to 73,
R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이고,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 내지 r13은 각각 0 내지 6의 정수이고,r11 to r13 are each an integer of 0 to 6,
r11 내지 r13이 2 이상인 경우, 괄호 안의 치환기는 서로 같거나 상이하고,When r11 to r13 are 2 or more, the substituents in parentheses are the same as or different from each other,
X, Ar, L, R2 내지 R5, 및 r2 내지 r5는 상기 화학식 1에서 정의한 바와 같다.X, Ar, L, R2 to R5, and r2 to r5 are as defined in Formula 1 above.
본 발명의 일 실시상태에 따르면, 상기 R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 또는 치환 또는 비치환된 6 내지 30의 아릴기이다. 본 발명의 다른 실시상태에 따르면, 상기 R11 내지 13은 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 탄소수 1 내지 10의 알킬기; 또는 치환 또는 비치환된 6 내지 20의 아릴기이다.According to an exemplary embodiment of the present invention, 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. According to another exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 또는 치환 또는 비치환된 나프틸기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 페닐기; 바이페닐기; 또는 나프틸기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 치환 또는 비치환된 페닐기; 또는 치환 또는 비치환된 나프틸기이다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 페닐기; 또는 나프틸기이다.According to an exemplary embodiment of the present invention, R11 to R13 are the same as or different from each other, and each independently hydrogen; phenyl group; or a naphthyl group.
본 발명의 일 실시상태에 따르면, 상기 R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소 또는 중수소이다.According to an exemplary embodiment of the present invention, R11 to R13 are the same as or different from each other, and each independently represent hydrogen or deuterium.
본 발명의 일 실시상태에 따르면, 상기 R11 내지 R13은 각각 수소이다.According to an exemplary embodiment of the present invention, R11 to R13 are each hydrogen.
본 발명의 일 실시상태에 따르면, r11은 0의 정수이다. 본 발명의 다른 일 실시상태에 따르면, r11은 1의 정수이다. 본 발명의 또 다른 실시상태에 따르면, r11은 2의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r11은 3의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r11은 4의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r11은 5의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r11은 6의 정수이다. r11이 2 이상인 경우, 괄호 안의 R11은 서로 같거나 상이하다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, r12는 0의 정수이다. 본 발명의 다른 일 실시상태에 따르면, r12는 1의 정수이다. 본 발명의 또 다른 실시상태에 따르면, r12는 2의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r12는 3의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r12는 4의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r12는 5의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r12는 6의 정수이다. r12가 2 이상인 경우, 괄호 안의 R12는 서로 같거나 상이하다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, r13은 0의 정수이다. 본 발명의 다른 일 실시상태에 따르면, r13은 1의 정수이다. 본 발명의 또 다른 실시상태에 따르면, r13은 2의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r13은 3의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r13은 4의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r13은 5의 정수이다. 본 발명의 또 다른 일 실시상태에 따르면, r13은 6의 정수이다. r13이 2 이상인 경우, 괄호 안의 R13은 서로 같거나 상이하다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 화학식 1은 하기 화합물 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present invention, Formula 1 is any one selected from the following compounds.
Figure PCTKR2021014328-appb-img-000015
Figure PCTKR2021014328-appb-img-000015
Figure PCTKR2021014328-appb-img-000016
Figure PCTKR2021014328-appb-img-000016
Figure PCTKR2021014328-appb-img-000017
Figure PCTKR2021014328-appb-img-000017
Figure PCTKR2021014328-appb-img-000018
Figure PCTKR2021014328-appb-img-000018
Figure PCTKR2021014328-appb-img-000019
Figure PCTKR2021014328-appb-img-000019
Figure PCTKR2021014328-appb-img-000020
Figure PCTKR2021014328-appb-img-000020
Figure PCTKR2021014328-appb-img-000021
Figure PCTKR2021014328-appb-img-000021
Figure PCTKR2021014328-appb-img-000022
Figure PCTKR2021014328-appb-img-000022
Figure PCTKR2021014328-appb-img-000023
.
Figure PCTKR2021014328-appb-img-000023
.
본 발명의 일 실시상태에 따른 화학식 1로 표시되는 화합물은 당 기술분야에 알려져 있는 방법 또는 후술할 합성예에 의하여 합성될 수 있으며, 치환기의 종류, 위치 또는 개수는 당 기술분야에 알려져 있는 기술에 따라 변경될 수 있다. 구체적인 합성예는 후술한다.The compound represented by Formula 1 according to an exemplary embodiment of the present invention 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.
본 발명의 일 실시상태는 양극; 음극; 및 상기 양극 및 상기 음극 사이에 구비된 유기물층을 포함하고, 상기 유기물층은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자를 제공한다. 일 예시로서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 발광층이다.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. As an example, the organic material layer including the compound represented by Formula 1 is a light emitting layer.
본 발명의 다른 일 실시상태에 따르면, 상기 유기 발광 소자는 2층 이상의 유기물층을 포함하고, 상기 2층 이상의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함한다. 예컨대, 상기 2층 이상의 유기물층 중 어느 1층의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함하고, 나머지 1층 이상의 유기물층을 더 포함한다. 일 실시상태에 따른 상기 나머지 1층 이상의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함하지 않는다. 다른 일 실시상태에 따른 상기 나머지 1층 이상의 유기물층은 상기 화학식 1로 표시되는 화합물을 더 포함한다. 다만, 상기 예시에 한정되는 것은 아니다. 상기 2층 이상의 유기물층은 예를 들어, 정공 주입층, 정공 수송층, 정공 주입 및 수송층, 전자 차단층, 발광층, 정공 차단층, 전자 수송층, 전자 주입층, 전자 주입 및 수송층 등으로 이루어진 군으로부터 선택되는 2층 또는 그 이상의 층을 포함한다. 이때, 정공 주입 및 수송층은 정공 주입과 정공 수송을 동시에 하는 층을 의미하고, 전자 주입 및 수송층은 전자 주입과 전자 수송을 동시에 하는 층을 의미한다. 그러나, 상기 군을 이루는 유기물층은 일 예시에 불과하고, 상기 예시에 한정되는 것은 아니다. 구체적인 일 예시로, 상기 유기 발광 소자에 포함된 유기물층은 2층 이상의 유기물층이고, 어느 1층의 유기물층은 발광층이고, 나머지 1층 이상의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함한다. 더 구체적인 일 예시로, 상기 유기 발광 소자에 포함된 유기물층은 2층 이상의 유기물층이고, 어느 1층의 유기물층은 발광층이고, 나머지 유기물층 중 어느 1층의 유기물층은 전자 차단층이고, 상기 전자 차단층은 상기 화학식 1로 표시되는 화합물을 포함한다.According to another exemplary embodiment of the present invention, 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. For example, 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. However, it is not limited to the above example. 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. In this case, the hole injection and transport layer means a layer that simultaneously injects and transports holes, and the electron injection and transport layer means a layer that simultaneously injects and transports electrons. However, the organic material layer constituting the group is only an example, and is not limited thereto. As a specific example, 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. As a more specific example, 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).
또한, 상기 2층 이상의 유기물층은 필요에 따라, 같은 역할을 수행하는 층을 2층 이상 포함할 수 있다. 일 예시에 따른 유기 발광 소자는 제1 전자 차단층 및 제2 전자 차단층을 포함한다. 다만, 상기 예시에 한정되는 것은 아니다. 상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다.In addition, 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. When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
본 발명의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함한다. 일 예시로서, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함한다. 구체적인 일 예시로서, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 발광층의 호스트로서 포함한다. 구체적인 다른 일 예시로서, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 발광층의 도펀트로서 포함한다.According to an exemplary embodiment of the present invention, the organic material layer includes a light emitting layer. As an example, the light emitting layer includes the compound represented by Formula 1 above. As a specific example, the light emitting layer includes the compound represented by Formula 1 as a host of the light emitting layer. As another specific example, the light emitting layer includes the compound represented by Formula 1 as a dopant of the light emitting layer.
본 발명의 일 실시상태에 따르면, 상기 유기물층은 전자 차단층, 정공 차단층, 정공 주입층, 정공 수송층, 정공 주입 및 수송층으로 이루어진 군으로부터 선택되는 1층 이상의 층을 더 포함한다. 일 예시로서, 상기 전자 차단층, 상기 정공 차단층, 상기 정공 주입층, 상기 정공 수송층, 상기 정공 주입 및 수송층으로 이루어진 군으로부터 선택되는 1층 이상의 층은 상기 화학식 1로 표시되는 화합물을 포함한다.According to an exemplary embodiment of the present invention, 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. As an example, 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.
이하에서는 상기 유기물층 및 이를 포함하는 유기 발광 소자의 적층 구조를 구체적으로 설명한다.Hereinafter, the organic material layer and the stacked structure of the organic light emitting device including the same will be described in detail.
본 발명의 일 실시상태에 따른 유기 발광 소자의 유기물층은 단층 구조이다. 예컨대, 상기 단층 구조의 유기물층은 유기 발광 소자의 양극 및 음극 사이에 구비되고, 상기 유기물층은 상기 화학식 1로 표시되는 화합물을 포함한다. 구체적인 일 실시상태에 따르면, 상기 단층 구조로 이루어진 유기물층은 발광층이고, 이때 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함한다.The organic material layer of the organic light emitting device according to an exemplary embodiment of the present invention has a single-layer structure. For example, 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. According to a specific exemplary embodiment, 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.
본 발명의 다른 일 실시상태에 따른 유기 발광 소자의 유기물층은 2층 이상의 유기물층이 적층된 다층 구조이다. 예컨대, 상기 다층 구조의 유기물층은 상기 유기 발광 소자의 양극 및 음극 사이에 구비된다.The organic material layer of the organic light emitting device according to another exemplary embodiment of the present invention has a multilayer structure in which two or more organic material layers are stacked. For example, the organic material layer having the multi-layer structure is provided between the anode and the cathode of the organic light emitting device.
본 발명의 일 실시상태에 따르면, 상기 다층 구조의 유기물층은 발광층 및 발광층 이외의 유기물층을 포함한다. 일 예시로서, 상기 발광층은 양극 및 음극 사이에 구비되고, 상기 발광층 이외의 유기물층은 양극 및 발광층 사이에 구비된다. 다른 일 예시로서, 상기 발광층은 양극 및 음극 사이에 구비되고, 상기 발광층 이외의 유기물층은 발광층 및 음극 사이에 구비된다. 또 다른 일 예시로서, 상기 발광층은 양극 및 음극 사이에 구비되고, 상기 발광층 이외의 어느 하나의 유기물층은 양극 및 발광층 사이에 구비되고, 상기 발광층 이외의 다른 어느 하나의 유기물층은 발광층 및 음극 사이에 구비된다. 다만, 상기 구조는 예시일 뿐이고, 상기 구조에 한정되는 것은 아니다. 또한, 상기 발광층 이외의 유기물층은 예를 들어, 정공 주입 및 수송층, 정공 주입층, 정공 수송층, 전자 차단층, 정공 차단층, 전자 수송층, 전자 주입층, 전자 주입 및 수송층 등으로 이루어진 군으로부터 선택되는 1층 이상의 층일 수 있으나, 이에 한정되는 것은 아니다.According to an exemplary embodiment of the present invention, 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. As an example, 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. As another example, 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. As another example, 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. However, the structure is merely an example, and is not limited thereto. In addition, 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.
일반적으로 유기 발광 소자에서 정공 주입층, 정공 수송층 또는 전자 차단층은 양극 및 발광층 사이에 구비된다. 구체적인 예로서, 정공 주입층은 양극 상부에 구비되고, 정공 수송층은 정공 주입층 상부에 구비되고, 전자 차단층은 정공 주입층 상부에 구비되나, 상기 예시에 한정되는 것은 아니다.In general, in an organic light emitting device, a hole injection layer, a hole transport layer, or an electron blocking layer is provided between the anode and the light emitting layer. As a specific example, the hole injection layer is provided on the anode, the hole transport layer is provided on the hole injection layer, and the electron blocking layer is provided on the hole injection layer, but the example is not limited thereto.
또한, 일반적으로 유기 발광 소자에서 전자 주입층, 전자 수송층 또는 정공 차단층은 음극 및 발광층 사이에 구비된다. 구체적인 예로서, 정공 차단층은 발광층 상부에 구비되고, 전자 수송층은 정공 차단층 상부에 구비되고, 전자 주입층은 전자 수송층 상부에 구비되나, 상기 예시에 한정되는 것은 아니다.Also, in general, in an organic light emitting device, an electron injection layer, an electron transport layer, or a hole blocking layer is provided between the cathode and the light emitting layer. As a specific example, the hole blocking layer is provided on the emission layer, the electron transport layer is provided on the hole blocking layer, and the electron injection layer is provided on the electron transport layer, but is not limited to the above example.
본 발명의 일 실시상태에 따른 유기 발광 소자에 포함된 다층 구조의 유기물층은 발광층; 및 정공 주입 및 수송층, 정공 주입층, 정공 수송층, 전자 차단층, 정공 차단층, 전자 수송층, 전자 주입층 및 전자 주입 및 수송층으로 이루어진 군으로부터 선택되는 1층 이상의 유기물층을 포함하고, 상기 발광층은 양극 및 음극 사이에 구비된다.The organic material layer having a multilayer structure included in the organic light emitting device according to an exemplary embodiment of the present invention 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.
본 발명의 바람직한 일 실시상태에 따르면, 상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 정공 주입 및 수송층 및 전자 차단층 중 적어도 하나이다. 더 바람직하게는, 상기 1층 이상의 유기물층은 전자 차단층이다.According to a preferred embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 유기물층은 전자 차단층을 포함하고, 상기 전자 차단층은 상기 화학식 1로 표시되는 화합물을 포함한다.According to an exemplary embodiment of the present invention, the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound represented by Formula 1 above.
본 발명의 일 실시상태에 따르면, 상기 유기물층은 정공 주입층을 포함한다.According to an exemplary embodiment of the present invention, the organic material layer includes a hole injection layer.
본 발명의 일 실시상태에 따르면, 상기 유기물층은 정공 수송층을 포함한다.According to an exemplary embodiment of the present invention, the organic material layer includes a hole transport layer.
본 발명의 일 실시상태에 따르면, 상기 유기물층은 정공 주입 및 수송층을 포함한다.According to an exemplary embodiment of the present invention, the organic material layer includes a hole injection and transport layer.
본 발명의 일 실시상태에 따르면, 상기 유기물층은 정공 주입층; 정공 수송층; 정공 주입 및 수송층; 및 전자 차단층으로 이루어진 군으로부터 선택되는 1 이상의 층을 포함한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 유기물층은 발광층; 및 정공 주입층; 정공 수송층; 정공 주입 및 수송층; 및 전자 차단층으로 이루어진 군으로부터 선택되는 1 이상의 층을 포함하고, 상기 정공 주입층; 정공 수송층; 정공 주입 및 수송층; 및 전자 차단층으로 이루어진 군으로부터 선택되는 1 이상의 층은 상기 화합물을 포함한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 따르면, 상기 유기물층은 정공 주입층, 정공 수송층, 또는 정공 주입 및 수송층을 포함하고, 상기 정공 주입층, 정공 수송층, 또는 정공 주입 및 수송층은 상기 화합물을 포함할 수 있다.According to an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태는 양극; 음극; 및 상기 양극 및 상기 음극 사이에 구비된 1층 이상의 유기물층을 포함하고, 상기 1층 이상의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자를 제공한다. 본 발명의 다른 일 실시상태는 양극; 음극; 및 상기 양극 및 상기 음극 사이에 구비된 2층 이상의 유기물층을 포함하고, 상기 2층 이상의 유기물층은 발광층; 및 정공 주입층, 정공 수송층, 정공 주입 및 수송층 및 전자 차단층 중 적어도 하나의 층을 포함하고, 상기 정공 주입층, 정공 수송층, 정공 주입 및 수송층 및 전자 차단층 중 적어도 하나의 층은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자를 제공한다. 본 발명의 구체적인 일 실시상태는 양극; 음극; 및 상기 양극 및 상기 음극 사이에 구비된 2층 이상의 유기물층을 포함하고, 상기 2층 이상의 유기물층은 발광층; 및 전자 차단층을 포함하고, 상기 전자 차단층은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자를 제공한다.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.
상기 유기 발광 소자는 예컨대 하기와 같은 적층 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.The organic light emitting device may have, for example, a stacked structure as follows, but is not limited thereto.
(1) 양극/정공 수송층/발광층/음극(1) anode/hole transport layer/light emitting layer/cathode
(2) 양극/정공 주입층/정공 수송층/발광층/음극(2) anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) 양극/정공 주입층/정공버퍼층/정공 수송층/발광층/음극(3) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / cathode
(4) 양극/정공 수송층/발광층/전자 수송층/음극(4) anode/hole transport layer/light emitting layer/electron transport layer/cathode
(5) 양극/정공 수송층/발광층/전자 수송층/전자 주입층/음극(5) anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(6) 양극/정공 주입층/정공 수송층/발광층/전자 수송층/음극(6) anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(7) 양극/정공 주입층/정공 수송층/발광층/전자 수송층/전자 주입층/음극(7) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode
(8) 양극/정공 주입층/정공버퍼층/정공 수송층/발광층/전자 수송층/음극(8) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode
(9) 양극/정공 주입층/정공버퍼층/정공 수송층/발광층/전자 수송층/전자 주입층 /음극(9) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode
(10) 양극/ 정공 수송층/전자 차단층/발광층/전자 수송층/음극(10) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode
(11) 양극/ 정공 수송층/전자 차단층/발광층/전자 수송층/전자 주입층/음극(11) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode
(12) 양극/정공 주입층/정공 수송층/전자 차단층/발광층/전자 수송층/음극(12) anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(13) 양극/정공 주입층/정공 수송층/전자 차단층/발광층/전자 수송층/전자 주입 층/음극(13) anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(14) 양극/정공 수송층/발광층/정공 차단층/전자 수송층/음극(14) anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(15) 양극/정공 수송층/발광층/정공 차단층/전자 수송층/전자 주입층/음극(15) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode
(16) 양극/정공 주입층/정공 수송층/발광층/정공 차단층/전자 수송층/음극(16) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode
(17) 양극/정공 주입층/정공 수송층/발광층/정공 차단층/전자 수송층/전자 주입 층/음극(17) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode
(18) 양극/정공 주입층/정공 수송층/발광층/정공 차단층/전자 수송층/전자 주입 층/음극/캡슐(18) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capsule
(19) 양극/정공 주입층/제1 정공 수송층/제2 정공 수송층/발광층/정공 차단층/전자 수송층/전자 주입 층/음극/캡슐(19) anode / hole injection layer / first hole transport layer / second hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode / capsule
본 발명의 유기 발광 소자의 구조는 도 1 및 도 2에 나타낸 것과 같은 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.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.
도 1에는 기판(1), 양극(2), 유기물층(3) 및 음극(10)이 순차적으로 적층된 유기 발광 소자의 구조가 예시 되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1의 화합물은 유기물층(3)에 포함될 수 있다.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. In such a structure, the compound of Formula 1 may be included in the organic material layer 3 .
도 2에는 기판(1), 양극(2), 정공 주입층(4), 정공 수송층(5), 전자 차단층(100), 발광층(6), 정공 차단층(7), 전자 주입 및 수송층(8) 및 음극(10)이 순차적으로 적층된 유기 발광 소자의 구조가 예시 되어 있다. 이와 같은 구조에 있어서, 상기 화학식 1의 화합물은 전자 차단층(100)에 포함될 수 있다.2 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. In such a structure, the compound of Formula 1 may be included in the electron blocking layer 100 .
본 발명의 일 실시상태에 있어서, 상기 유기 발광 소자는 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다.In an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 있어서, 상기 유기 발광 소자는 기판 상에 음극, 1층 이상의 유기물층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다.In one embodiment of the present invention, 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.
본 발명에서 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In the present invention, 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.
본 발명에서 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다. In the present invention, when a part "includes" a certain component, this means that other components may be further included, rather than excluding other components, unless otherwise stated.
본 발명에 있어서, 상기 "층"은 본 기술분야에 주로 사용되는 '필름'과 호환되는 의미이며, 목적하는 영역을 덮는 코팅을 의미한다. 상기 "층"의 크기는 한정되지 않으며, 각각의 "층"은 그 크기가 동일하거나 상이할 수 있다. 일 실시상태에 있어서, "층"의 크기는 전체 소자와 같을 수 있고, 특정 기능성 영역의 크기에 해당할 수 있으며, 단일 서브픽셀(sub-pixel)만큼 작을 수도 있다. In the present invention, 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.
본 발명에 있어서, 특정한 A 물질이 B층에 포함된다는 의미는 i) 1종 이상의 A 물질이 하나의 B층에 포함되는 것과 ii) B층이 1층 이상으로 구성되고, A 물질이 다층의 B층 중 1층 이상에 포함되는 것을 모두 포함한다.In the present invention, 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.
본 발명에 있어서, 특정한 A 물질이 C층 또는 D층에 포함된다는 의미는 i) 1층 이상의 C층 중 1층 이상에 포함되거나, ii) 1층 이상의 D층 중 1층 이상에 포함되거나, iii) 1층 이상의 C층 및 1층 이상의 D층에 각각 포함되는 것을 모두 의미하는 것이다. In the present invention, 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.
본 발명의 일 실시상태에 있어서, 상기 발광층은 호스트 및 도펀트를 포함한다. 상기 발광층에 사용되는 호스트 및 도펀트는 당 기술분야에 공지된 재료를 이용할 수 있다.In an exemplary embodiment of the present invention, the light emitting layer includes a host and a dopant. As the host and dopant used in the light emitting layer, materials known in the art may be used.
본 발명의 일 실시상태에 있어서, 상기 도펀트는 인광 도펀트 또는 형광 도펀트를 포함한다. 형광 도펀트로서는 당 기술분야에 공지된 아릴아민계 화합물 또는 보론 화합물을 포함할 수 있으나, 이에 한정되지 않는다.In an exemplary embodiment of the present invention, 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.
본 발명의 일 실시상태에 있어서, 상기 유기물층은 알칼리 금속 및 알칼리토금속 중에서 선택되는 1종 또는 2종 이상의 n형 도펀트를 더 포함한다.In an exemplary embodiment of the present invention, the organic material layer further includes one or two or more n-type dopants selected from alkali metals and alkaline earth metals.
유기 알칼리 금속 화합물 또는 유기 알칼리 토금속 화합물이 n 형 도펀트로 사용되는 경우에는 발광층으로부터 정공에 대한 안정성을 확보할 수 있어, 유기 발광 소자의 수명을 향상시킬 수 있다. 또한, 전자 수송층의 전자이동도를 유기 알칼리 금속 화합물 또는 유기 알칼리 토금속 화합물의 비율을 조절하여 발광층에서 정공과 전자의 균형을 극대화시켜 발광 효율을 증가시킬 수 있다. When 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. In addition, by adjusting 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.
본 발명에서 유기물층에 사용되는 n형 도펀트로서 LiQ가 더욱 바람직하다. LiQ is more preferable as the n-type dopant used in the organic material layer in the present invention.
본 발명의 일 실시상태에 따르면, 상기 유기 발광 소자는 두 개 이상의 독립된 소자가 직렬로 연결된 탠덤 구조일 수 있다. 일 실시상태에 있어서, 상기 탠덤 구조는 각각의 유기 발광 소자가 전하 생성층으로 접합된 형태일 수 있다. 탠덤 구조의 소자는 같은 밝기를 기준으로 단위 소자보다 낮은 전류에서 구동 가능하므로, 소자의 수명 특성이 크게 향상되는 장점이 있다.According to an exemplary embodiment of the present invention, the organic light emitting device may have a tandem structure in which two or more independent devices are connected in series. In an exemplary embodiment, 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.
본 발명의 일 실시상태에 따르면, 상기 유기물층은 1층 이상의 발광층을 포함하는 제1 스택; 1층 이상의 발광층을 포함하는 제2 스택; 및 상기 제1 스택과 상기 제2 스택의 사이에 구비된 1층 이상의 전하 생성층을 포함한다.According to an exemplary embodiment of the present invention, 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.
본 발명의 다른 실시상태에 따르면, 상기 유기물층은 1층 이상의 발광층을 포함하는 제1 스택; 1층 이상의 발광층을 포함하는 제2 스택; 및 1층 이상의 발광층을 포함하는 제3 스택을 포함하고, 상기 제1 스택과 상기 제2 스택의 사이; 및 상기 제2 스택과 상기 제3 스택의 사이에 각각 1층 이상의 전하 생성층을 포함한다.According to another exemplary embodiment of the present invention, 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.
본 발명에 있어서, 전하 생성층(Charge Generating layer)이란 전압을 걸면 정공과 전자가 발생하는 층을 의미한다. 상기 전하 생성층은 N형 전하 생성층 또는 P형 전하 생성층일 수 있다. 본 발명에서, N형 전하 생성층이란 P형 전하 생성층보다 양극에 가깝게 위치한 전하 생성층을 의미하고, P형 전하 생성층이란 N형 전하 생성층보다 음극에 가깝게 위치한 전하 생성층을 의미한다.In the present invention, the charge generating layer (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. In the present invention, the N-type charge generation layer means a charge generation layer located closer to the anode than the P-type charge generation layer, and the P-type charge generation layer means a charge generation layer located closer to the cathode than the N-type charge generation layer.
상기 N형 전하 생성층 및 P형 전하 생성층은 접하여 구비될 수 있으며, 이 경우 NP 접합을 형성한다. NP 접합에 의하여 P형 전하 생성층 내에서 정공이, N형 전하 생성층 내에서 전자가 용이하게 형성된다. 전자는 N형 전하 생성층의 LUMO 준위를 통하여 양극 방향으로 수송되고, 정공은 P형 유기물층의 HOMO 준위를 통하여 음극 방향으로 수송된다.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. By the NP junction, holes are easily formed in the P-type charge generation layer and electrons are easily formed in the N-type charge generation layer. 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.
상기 제1 스택, 제2 스택 및 제3 스택은 각각 1층 이상의 발광층을 포함하며, 추가로 정공 주입층, 정공 수송층, 전자 차단층, 전자 주입층, 전자 수송층, 정공 차단층, 정공 수송 및 정공 주입을 동시에 하는 층(정공 주입 및 수송층), 및 전자 수송 및 전자 주입을 동시에 하는 층(전자 주입 및 수송층) 중 1층 이상의 층을 더 포함할 수 있다.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).
본 발명의 유기 발광 소자는 유기물층이 상기 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다.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.
예컨대, 본 발명의 유기 발광 소자는 기판 상에 양극, 유기물층 및 음극을 순차적으로 적층시킴으로써 제조할 수 있다. 이 때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 전자 차단층, 발광층, 정공 차단층, 전자 수송층 또는 전자 주입층을 포함하는 유기물층을 형성한 후, 그 위에 음극로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 음극 물질, 유기물층 및 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다. 다만, 제조 방법이 이에 한정되는 것은 아니다.For example, 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. At this time, by using 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. After forming 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. can In addition to this method, 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. However, the manufacturing method is not limited thereto.
또한, 화합물은 유기 발광 소자의 제조 시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하나, 이에 한정되는 것은 아니다. In addition, 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. Here, 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.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 예를 들어, 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이에 한정되는 것은 아니다. As the anode material, a material having a large work function is generally preferred so that holes can be smoothly injected into the organic material layer. For example, 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.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 예를 들어, 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이에 한정되는 것은 아니다.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.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다.The emission layer may include a host material and a dopant material.
상기 호스트 재료로는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로, 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되는 것은 아니다. Examples of the host material include a condensed aromatic ring derivative or a heterocyclic compound containing compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, and the like, and heterocyclic-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but is not limited thereto.
상기 도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로, 방향족 아민 유도체로는 치환 또는 비치환된 아릴아민기를 갖는 축합 방향족환 유도체로서, 아릴아민기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있다. 또한, 스티릴아민 화합물은 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 시클로알킬기 및 아릴아민기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되는 것은 아니다. Examples of the dopant material include an aromatic amine derivative, a strylamine compound, a boron complex, a fluoranthene compound, and a metal complex. Specifically, 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. In addition, 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. Specifically, there are styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto.
상기 정공 주입층은 전극으로부터 정공을 수취하는 층이다. 정공 주입 물질은 정공을 수송하는 능력을 가져 양극으로부터 정공 수취 효과 및 발광층 또는 발광 재료에 대하여 우수한 정공 주입 효과를 갖는 것이 바람직하다. 또한, 발광층에서 생성된 엑시톤의 전자 주입층 또는 전자 주입 재료에의 이동을 방지할 수 있는 능력이 우수한 물질이 바람직하다. 또한, 박막 형성 능력이 우수한 물질이 바람직하다. 또한, 정공 주입 물질의 HOMO가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는, 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물; 헥사니트릴헥사아자트리페닐렌 계열의 유기물; 퀴나크리돈(quinacridone)계열의 유기물; 페릴렌(perylene) 계열의 유기물; 안트라퀴논, 폴리아닐린과 같은 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이에 한정 되는 것은 아니다. 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. Specific examples of the 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.
상기 정공 수송층은 정공 주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 단층 또는 2층 이상의 다층구조일 수 있다. 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수취하여 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 바람직하다. 구체적인 예로는, 아릴아민 계열의 유기물, 카바졸계 화합물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이에 한정되는 것은 아니다.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.
상기 전자 수송층은 전자 주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층이다. 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 바람직하다. 구체적인 예로는, 8-히드록시퀴놀린의 Al착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이에 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이, 임의의 원하는 음극 물질과 함께 사용할 수 있다. 특히, 적절한 음극 물질은 낮은 일함수를 가지며, 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로, 세슘, 바륨, 칼슘, 이테르븀 및 사마륨 등이 있고, 각 경우 알루미늄층 또는 실버층이 뒤따른다.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. In particular, 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.
상기 전자 주입층은 전극으로부터 전자를 수취하는 층이다. 전자 주입 물질로는 전자를 수송하는 능력이 우수하고, 음극으로부터의 전자 수취 효과, 발광층 또는 발광 재료에 대하여 우수한 전자 주입 효과를 갖는 것이 바람직하다. 또한, 발광층에서 생성된 엑시톤이 정공 주입층으로 이동하는 것을 방지하고, 박막 형성 능력이 우수한 물질이 바람직하다. 구체적으로는, 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되는 것은 아니다. The electron injection layer is a layer that receives electrons from the electrode. As 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. In addition, 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. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, preorenylidene methane, anthrone, etc. derivatives thereof; metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
상기 금속 착체 화합물로는 8-히드록시퀴놀리나토 리튬, 비스(8-히드록시퀴놀리나토)아연, 비스(8-히드록시퀴놀리나토)구리, 비스(8-히드록시퀴놀리나토)망간, 트리스(8-히드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-히드록시퀴놀리나토)알루미늄, 트리스(8-히드록시퀴놀리나토)갈륨, 비스(10-히드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-히드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되는 것은 아니다.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.
상기 전자 차단층은 전자 주입층으로부터 주입된 전자가 발광층을 지나 정공 주입층으로 진입하는 것을 방지하여 소자의 수명과 효율을 향상시킬 수 있는 층이다. 상기 전자 차단층은 상기 발광층과 정공 주입층 사이에, 또는 상기 발광층과 정공 주입 및 정공 수송을 동시에 하는 층 사이에 형성될 수 있다. 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.
상기 정공 차단층은 정공의 음극으로 도달을 저지하는 층으로, 일반적으로 전자 주입층과 동일한 조건으로 형성될 수 있다. 상기 정공 차단층 물질로는 구체적으로, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되는 것은 아니다. 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. Specifically, 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.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.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.
본 발명의 일 실시상태는 상기 화학식 1의 화합물을 포함하는 유기 발광 소자를 포함하는 전자 소자를 제공한다.An exemplary embodiment of the present invention provides an electronic device including an organic light emitting device including the compound of Formula 1 above.
상기 전자 소자는 반도체 소자의 층간 절연막, 컬러필터, 블랙 매트릭스, 오버 코트, 컬럼 스페이서, 패시베이션막, 버퍼 코트막, 다층 프린트 기판용 절연막, 플렉서블 구리 피복판의 커버 코트, 버퍼코트 막, 다층 프린트 기판용 절연막솔더 레지스트막, OLED의 절연막, 액정표시소자의 박막 트랜지스터의 보호막, OLED용 다이오드, 유기 EL 소자의 전극보호막 및 반도체 보호막, OLED 절연막, LCD 절연막, 반도체 절연막, 태양광 모듈, 터치 패널, 디스플레이 패널 등의 디스플레이 장치 등을 모두 포함하는 것일 수 있으나, 이에 한정되는 것은 아니다.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.
이하, 본 발명을 구체적으로 설명하기 위해 실시예 및 비교예 등을 들어 상세하게 설명하기로 한다. 그러나, 본 발명에 따른 실시예 및 비교예는 여러 가지 다른 형태로 변형될 수 있으며, 본 발명의 범위가 아래에서 상술하는 실시예 및 비교예에 한정되는 것으로 해석되지 않는다. 본 발명의 실시예 및 비교예는 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, examples and comparative examples will be given to describe the present invention in detail. However, the Examples and Comparative Examples according to the present invention may be modified in various other forms, and the scope of the present invention is not to be construed as being limited to the Examples and Comparative Examples described in detail below. Examples and comparative examples of the present invention are provided to more completely explain the present specification to those of ordinary skill in the art.
<제조예><Production Example>
제조예 1Preparation Example 1
Figure PCTKR2021014328-appb-img-000024
Figure PCTKR2021014328-appb-img-000024
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A (8.20 g, 23.17 mmol), 및 화합물 a-1(7.93 g, 23.64 mmol)을 톨루엔 348 mL에 완전히 녹인 후 NaOtBu(3.34 g, 34.76 mmol)을 첨가하고, 비스(트리-터트-부틸포스핀) 팔라듐(0)(Bis(tri-tert-butylphosphine) palladium(0)) (0.59 g, 1.16 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과(filter)하여 염기(base)를 제거한 후 톨루엔을 감압농축시키고, 에틸아세테이트 250 mL으로 재결정하여 화합물 1(12.5 g, 수율: 83%)를 제조하였다.Compound A (8.20 g, 23.17 mmol) and compound a-1 (7.93 g, 23.64 mmol) were completely dissolved in 348 mL of toluene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (3.34 g, 34.76 mmol) was added thereto. , bis(tri-tert-butylphosphine) palladium(0)(Bis(tri-tert-butylphosphine)palladium(0)) (0.59 g, 1.16 mmol) was added, and the mixture was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure, and recrystallized from 250 mL of ethyl acetate to prepare Compound 1 (12.5 g, yield: 83%).
MS[M+H]+= 653MS[M+H]+= 653
제조예 2 Preparation 2
Figure PCTKR2021014328-appb-img-000025
Figure PCTKR2021014328-appb-img-000025
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A (7.50 g, 21.20 mmol), 및 화합물 a-2(8.33 g, 21.62 mmol)을 톨루엔 318 mL에 완전히 녹인 후 NaOtBu(3.06 g, 31.79 mmol)을 첨가하고, 비스(트리-터트-부틸포스핀) 팔라듐(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.54 g, 1.06 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과(filter)하여 염기(base)를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 250 mL으로 재결정하여 화합물 2(11.8 g, 수율: 79%)를 제조하였다.Compound A (7.50 g, 21.20 mmol) and compound a-2 (8.33 g, 21.62 mmol) were completely dissolved in toluene in 318 mL of toluene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (3.06 g, 31.79 mmol) was added thereto. , Bis(tri-tert-butylphosphine) palladium(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.54 g, 1.06 mmol) was added, and the mixture was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 2 (11.8 g, yield: 79%).
MS[M+H]+= 703MS[M+H]+= 703
제조예 3 Preparation 3
Figure PCTKR2021014328-appb-img-000026
Figure PCTKR2021014328-appb-img-000026
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A (7.20 g, 20.35 mmol), 및 화합물 a-3(9.58 g, 20.75 mmol)을 톨루엔 305 mL에 완전히 녹인 후 NaOtBu(2.93 g, 30.52 mmol)을 첨가하고, 비스(트리-터트-부틸포스핀) 팔라듐(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.52 g, 1.02 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과(filter)하여 염기(base)를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 250 mL으로 재결정하여 화합물 3(12.0 g, 수율: 76%)를 제조하였다.Compound A (7.20 g, 20.35 mmol) and compound a-3 (9.58 g, 20.75 mmol) were completely dissolved in 305 mL of toluene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (2.93 g, 30.52 mmol) was added thereto. , Bis(tri-tert-butylphosphine) palladium(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.52 g, 1.02 mmol) was added, and the mixture was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 3 (12.0 g, yield: 76%).
MS[M+H]+= 779MS[M+H]+= 779
제조예 4Preparation 4
Figure PCTKR2021014328-appb-img-000027
Figure PCTKR2021014328-appb-img-000027
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A (8.00 g, 22.61 mmol), 및 화합물 a-4(8.89 g, 23.06 mmol)을 톨루엔 340 mL에 완전히 녹인 후 NaOtBu(3.26 g, 33.91 mmol)을 첨가하고, 비스(트리-터트-부틸포스핀) 팔라듐(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.58 g, 1.13 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과(filter)하여 염기(base)를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 250 mL으로 재결정하여 화합물 4(13.0 g, 수율: 82%)를 제조하였다.Compound A (8.00 g, 22.61 mmol) and compound a-4 (8.89 g, 23.06 mmol) were completely dissolved in 340 mL of toluene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (3.26 g, 33.91 mmol) was added thereto. , bis(tri-tert-butylphosphine) palladium(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.58 g, 1.13 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 4 (13.0 g, yield: 82%).
MS[M+H]+= 703MS[M+H]+= 703
제조예 5Preparation 5
Figure PCTKR2021014328-appb-img-000028
Figure PCTKR2021014328-appb-img-000028
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A (7.50 g, 21.20 mmol), 및 화합물 a-5(7.47 g, 21.62 mmol)을 톨루엔 318 mL에 완전히 녹인 후 NaOtBu(3.06 g, 31.79 mmol)을 첨가하고, 비스(트리-터트-부틸포스핀) 팔라듐(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.54 g, 1.06 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과(filter)하여 염기(base)를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 250 mL으로 재결정하여 화합물 5(12.5 g, 수율: 78%)를 제조하였다.Compound A (7.50 g, 21.20 mmol) and compound a-5 (7.47 g, 21.62 mmol) were completely dissolved in toluene in 318 mL of toluene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (3.06 g, 31.79 mmol) was added thereto. , bis(tri-tert-butylphosphine) palladium(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.54 g, 1.06 mmol) was added, and the mixture was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 5 (12.5 g, yield: 78%).
MS[M+H]+= 753MS[M+H]+= 753
제조예 6 Preparation 6
Figure PCTKR2021014328-appb-img-000029
Figure PCTKR2021014328-appb-img-000029
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 B (6.80 g, 16.84 mmol), 및 화합물 a-6(7.07 g, 17.17 mmol)을 톨루엔 253 mL에 완전히 녹인 후 NaOtBu(2.43 g, 25.25 mmol)을 첨가하고, 비스(트리-터트-부틸포스핀) 팔라듐(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.43 g, 0.84 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과(filter)하여 염기(base)를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 250 mL으로 재결정하여 화합물 6(9.2 g, 수율: 70%)를 제조하였다.Compound B (6.80 g, 16.84 mmol) and compound a-6 (7.07 g, 17.17 mmol) were completely dissolved in 253 mL of toluene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (2.43 g, 25.25 mmol) was added thereto. , bis(tri-tert-butylphosphine) palladium(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.43 g, 0.84 mmol) was added, and the mixture was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 6 (9.2 g, yield: 70%).
MS[M+H]+= 779MS[M+H]+= 779
제조예 7 Preparation 7
Figure PCTKR2021014328-appb-img-000030
Figure PCTKR2021014328-appb-img-000030
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 C (6.50 g, 16.09 mmol), 및 화합물 a-7(6.75 g, 16.41 mmol)을 톨루엔 240 mL에 완전히 녹인 후 NaOtBu(2.32 g, 24.14 mmol)을 첨가하고, 비스(트리-터트-부틸포스핀) 팔라듐(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.41 g, 0.80 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과(filter)하여 염기(base)를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 230 mL으로 재결정하여 화합물 7(7.8 g, 수율: 62%)를 제조하였다.Compound C (6.50 g, 16.09 mmol) and compound a-7 (6.75 g, 16.41 mmol) were completely dissolved in 240 mL of toluene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (2.32 g, 24.14 mmol) was added thereto. , Bis(tri-tert-butylphosphine) palladium(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.41 g, 0.80 mmol) was added, and the mixture was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized from 230 mL of ethyl acetate to prepare compound 7 (7.8 g, yield: 62%).
MS[M+H]+= 779MS[M+H]+= 779
제조예 8 Preparation 8
Figure PCTKR2021014328-appb-img-000031
Figure PCTKR2021014328-appb-img-000031
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 D (7.00 g, 17.33 mmol), 및 화합물 a-8(6.81 g, 17.68 mmol)을 톨루엔 260 mL에 완전히 녹인 후 NaOtBu(2.50 g, 26.00 mmol)을 첨가하고, 비스(트리-터트-부틸포스핀) 팔라듐(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.44 g, 0.87 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 필터(filter)하여 염기(base)를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 250 mL으로 재결정하여 화합물 8(8.5 g, 수율: 65%)를 제조하였다.Compound D (7.00 g, 17.33 mmol) and compound a-8 (6.81 g, 17.68 mmol) were completely dissolved in toluene in 260 mL of toluene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (2.50 g, 26.00 mmol) was added thereto. , bis(tri-tert-butylphosphine) palladium(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.44 g, 0.87 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 8 (8.5 g, yield: 65%).
MS[M+H]+= 753MS[M+H]+= 753
제조예 9Preparation 9
Figure PCTKR2021014328-appb-img-000032
Figure PCTKR2021014328-appb-img-000032
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A (8.00 g, 22.61 mmol), 및 화합물 a-9(8.66 g, 23.06 mmol)을 톨루엔 340 mL에 완전히 녹인 후 NaOtBu(3.26 g, 33.91 mmol)을 첨가하고, 비스(트리-터트-부틸포스핀) 팔라듐(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.58 g, 1.13 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과(filter)하여 염기(base)를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 250 mL으로 재결정하여 화합물 9(11.4 g, 수율: 73%)를 제조하였다.Compound A (8.00 g, 22.61 mmol) and compound a-9 (8.66 g, 23.06 mmol) were completely dissolved in toluene in 340 mL of toluene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (3.26 g, 33.91 mmol) was added thereto. , bis(tri-tert-butylphosphine) palladium(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.58 g, 1.13 mmol) was added, followed by heating and stirring for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 9 (11.4 g, yield: 73%).
MS[M+H]+= 693MS[M+H]+= 693
제조예 10 Preparation 10
Figure PCTKR2021014328-appb-img-000033
Figure PCTKR2021014328-appb-img-000033
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A (7.40 g, 20.91 mmol), 및 화합물 a-10(10.40 g, 21.33 mmol)을 톨루엔 310 mL에 완전히 녹인 후 NaOtBu(3.01 g, 31.37 mmol)을 첨가하고, 비스(트리-터트-부틸포스핀) 팔라듐(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.53 g, 1.05 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과(filter)하여 염기(base)를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 250 mL으로 재결정하여 화합물 10(14.8 g, 수율: 88%)를 제조하였다.Compound A (7.40 g, 20.91 mmol) and compound a-10 (10.40 g, 21.33 mmol) were completely dissolved in toluene in 310 mL of toluene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (3.01 g, 31.37 mmol) was added thereto. , bis(tri-tert-butylphosphine) palladium(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.53 g, 1.05 mmol) was added, and the mixture was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 10 (14.8 g, yield: 88%).
MS[M+H]+= 805MS[M+H]+= 805
제조예 11Preparation 11
Figure PCTKR2021014328-appb-img-000034
Figure PCTKR2021014328-appb-img-000034
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A (8.2 g, 23.17 mmol), 및 화합물 a-11(11.29 g, 23.64 mmol)을 톨루엔 350 mL에 완전히 녹인 후 NaOtBu(3.34 g, 34.76 mmol)을 첨가하고, 비스(트리-터트-부틸포스핀) 팔라듐(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.59 g, 1.16 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과(filter)하여 염기(base)를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 250 mL으로 재결정하여 화합물 11(14.50 g, 수율: 79%)를 제조하였다.Compound A (8.2 g, 23.17 mmol) and compound a-11 (11.29 g, 23.64 mmol) were completely dissolved in 350 mL of toluene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (3.34 g, 34.76 mmol) was added thereto. , bis(tri-tert-butylphosphine) palladium(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.59 g, 1.16 mmol) was added, and the mixture was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 11 (14.50 g, yield: 79%).
MS[M+H]+= 795MS[M+H]+= 795
제조예 12Preparation 12
Figure PCTKR2021014328-appb-img-000035
Figure PCTKR2021014328-appb-img-000035
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 A (7.50 g, 21.20 mmol), 및 화합물 a-12(8.68 g, 21.62 mmol)을 톨루엔 320 mL에 완전히 녹인 후 NaOtBu(3.06 g, 31.79 mmol)을 첨가하고, 비스(트리-터트-부틸포스핀) 팔라듐(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.54 g, 1.06 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 여과(filter)하여 염기(base)를 제거한 후 톨루엔을 감압농축 시키고 에틸아세테이트 250 mL으로 재결정하여 화합물 12(12.30 g, 수율: 81%)를 제조하였다.Compound A (7.50 g, 21.20 mmol) and compound a-12 (8.68 g, 21.62 mmol) were completely dissolved in 320 mL of toluene in a 500 mL round bottom flask in a nitrogen atmosphere, and NaOtBu (3.06 g, 31.79 mmol) was added thereto. , bis(tri-tert-butylphosphine) palladium(0) (Bis(tri-tert-butylphosphine) palladium(0)) (0.54 g, 1.06 mmol) was added, and the mixture was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, toluene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to prepare compound 12 (12.30 g, yield: 81%).
MS[M+H]+= 719MS[M+H]+= 719
<실시예><Example>
실시예 1-1Example 1-1
ITO(indium tin oxide)가 1,000 Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with indium tin oxide (ITO) to a thickness of 1,000 Å was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a product manufactured by Fischer Co. was used as the detergent, and distilled water that was secondarily filtered with a filter manufactured by Millipore Co. was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic washing was performed for 10 minutes by repeating twice with distilled water. After washing 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. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.
이렇게 준비된 양극인 ITO 투명 전극 위에 하기 화합물 HI1 및 하기 화합물 HI2의 화합물을 98:2(몰비)의 비가 되도록 100 Å의 두께로 열 진공 증착하여 정공 주입층을 형성하였다. 상기 정공 주입층 위에 하기 화학식 HT1으로 표시되는 화합물(1150 Å)을 진공 증착하여 정공 수송층을 형성하였다. 이어서, 상기 정공 수송층 위에 막 두께 50 Å으로 제조예 1의 화합물 1을 진공 증착하여 전자 차단층을 형성하였다. 이어서, 상기 전자 차단층 위에 막 두께 200 Å으로 하기 화학식 BH로 표시되는 화합물 및 하기 화학식 BD로 표시되는 화합물을 25:1의 중량비로 진공증착하여 발광층을 형성하였다. 상기 발광층 위에 막 두께 50 Å으로 하기 화학식 HB1으로 표시되는 화합물을 진공 증착하여 정공 차단층을 형성하였다. 이어서, 상기 정공 차단층 위에 하기 화학식 ET1으로 표시되는 화합물과 하기 화학식 LiQ로 표시되는 화합물을 1:1의 중량비로 진공증착하여 310 Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 12Å 두께로 리튬플로라이드(LiF)와 1,000 Å 두께로 알루미늄을 증착하여 음극을 형성하였다.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 Å 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 Å) represented by the following formula HT1 on the hole injection layer. Next, compound 1 of Preparation Example 1 was vacuum-deposited to a thickness of 50 Å on the hole transport layer to form an electron blocking layer. Then, the compound represented by the following formula BH and the compound represented by the following formula BD to a thickness of 200 Å 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 Å on the emission layer. Then, on the hole blocking 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 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.
Figure PCTKR2021014328-appb-img-000036
Figure PCTKR2021014328-appb-img-000036
상기의 과정에서 유기물의 증착속도는 0.4 Å/sec 내지 0.7 Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3 Å/sec, 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착 시 진공도는 2＊10-7 torr 내지 5＊10-6 torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of organic material was maintained at 0.4 Å/sec to 0.7 Å/sec, the deposition rate of lithium fluoride of the negative electrode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum degree during deposition was An organic light emitting diode was manufactured by maintaining 2*10 -7 torr to 5*10 -6 torr.
실시예 1-2 내지 1-12Examples 1-2 to 1-12
실시예 1-2 내지 1-12는 실시예 1-1의 화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. In 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.
비교예 1-1 내지 1-8Comparative Examples 1-1 to 1-8
비교예 1-1 내지 1-8은 실시예 1-1의 화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서 사용한 EB1 내지 EB8의 화합물은 하기와 같다.In 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.
Figure PCTKR2021014328-appb-img-000037
Figure PCTKR2021014328-appb-img-000037
상기 실시예 1-1 내지 1-12 및 비교예 1-1 내지 1-8에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 1에 나타내었다. T95은 휘도가 초기 휘도(1600 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When a current was applied to the organic light emitting diodes prepared in Examples 1-1 to 1-12 and Comparative Examples 1-1 to 1-8, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. indicated. T95 denotes a time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
화합물(전자 차단층)compound (electron blocking layer) 전압(V@10mA/cm2)Voltage (V@10mA/cm 2 ) 효율(cd/A@10mA/cm2)Efficiency (cd/A@10mA/cm 2 ) 색좌표(x,y)Color coordinates (x,y) T95(hr)T95(hr)
실시예 1-1Example 1-1 화합물 1compound 1 4.104.10 6.856.85 (0.146, 0.047)(0.146, 0.047) 275275
실시예 1-2Example 1-2 화합물 2compound 2 4.124.12 6.626.62 (0.146, 0.047)(0.146, 0.047) 296296
실시예 1-3Examples 1-3 화합물 3compound 3 4.174.17 6.856.85 (0.145, 0.047)(0.145, 0.047) 310310
실시예 1-4Examples 1-4 화합물 4compound 4 4.234.23 6.746.74 (0.146, 0.046)(0.146, 0.046) 282282
실시예 1-5Examples 1-5 화합물 5compound 5 4.194.19 6.786.78 (0.145, 0.046)(0.145, 0.046) 295295
실시예 1-6Examples 1-6 화합물 6compound 6 4.304.30 6.686.68 (0.146, 0.046)(0.146, 0.046) 305305
실시예 1-7Examples 1-7 화합물 7compound 7 4.034.03 6.806.80 (0.145, 0.047)(0.145, 0.047) 260260
실시예 1-8Examples 1-8 화합물 8compound 8 4.104.10 6.766.76 (0.146, 0.046)(0.146, 0.046) 268268
실시예 1-9Examples 1-9 화합물 9compound 9 4.074.07 6.806.80 (0.145, 0.047)(0.145, 0.047) 255255
실시예 1-10Examples 1-10 화합물 10compound 10 4.154.15 6.686.68 (0.146, 0.046)(0.146, 0.046) 264264
실시예 1-11Examples 1-11 화합물 11compound 11 4.044.04 6.826.82 (0.145, 0.046)(0.145, 0.046) 298298
실시예 1-12Examples 1-12 화합물 12compound 12 4.604.60 6.686.68 (0.146, 0.047)(0.146, 0.047) 266266
비교예 1-1Comparative Example 1-1 EB1EB1 4.354.35 6.556.55 (0.146, 0.047)(0.146, 0.047) 198198
비교예 1-2Comparative Example 1-2 EB2EB2 4.444.44 6.486.48 (0.146, 0.046)(0.146, 0.046) 185185
비교예 1-3Comparative Example 1-3 EB3EB3 4.274.27 6.556.55 (0.145, 0.047)(0.145, 0.047) 198198
비교예 1-4Comparative Example 1-4 EB4EB4 4.424.42 6.526.52 (0.145, 0.047)(0.145, 0.047) 188188
비교예 1-5Comparative Example 1-5 EB5EB5 4.384.38 6.546.54 (0.146, 0.047)(0.146, 0.047) 175175
비교예 1-6Comparative Example 1-6 EB6EB6 4.404.40 6.496.49 (0.146, 0.047)(0.146, 0.047) 172172
비교예 1-7Comparative Example 1-7 EB7EB7 4.384.38 6.486.48 (0.145, 0.047)(0.145, 0.047) 180180
비교예 1-8Comparative Examples 1-8 EB8EB8 4.324.32 6.256.25 (0.145, 0.047)(0.145, 0.047) 203203
상기 표 1에 나타난 바와 같이, 본 발명의 일 실시상태에 따라 바이페닐기의 파라 부분에 아민기가 치환되고, 오르토 부분에 카바졸기가 치환된 화합물을 전자 차단층으로 사용한 유기 발광 소자는, 유기 발광 소자의 효율, 구동 전압 또는 수명 면에서 우수한 특성을 나타내었다.As shown in Table 1 above, according to an exemplary embodiment of the present invention, 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.
반면, 아민기와 결합한 디벤조퓨란기에 아릴기가 치환된 화합물은 본 발명의 일 실시상태에 따른 화합물에 비해, 구동 전압, 효율 및 안정성의 특성이 좋지 않았다. 아민기와 결합한 디벤조퓨란기에 바이페닐기가 치환된 상기 화합물 EB1 내지 EB3을 사용한 비교예 1-1 내지 1-3의 유기 발광 소자는 전압상승, 효율저하 및 수명저하 등 실시예에 비해 열화된 특성을 나타내었다.On the other hand, 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.
또한, 디벤조퓨란기가 아민기에 직접결합되지 않고 페닐렌기 등의 연결기(Linker)를 통해 결합된 화합물 EB4를 사용한 비교예 1-4의 경우, 유기 발광 소자의 특성이 디벤조퓨란기와 아민기가 직접결합한 실시예에 비해 전압상승, 효율저하 및 수명저하 등 열화된 특성을 보였다.In addition, in Comparative Examples 1-4 using the compound EB4 in which the dibenzofuran group is not directly bonded to the amine group but via a linker such as a phenylene group, 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.
그리고, 바이페닐기-아민기의 결합 위치, 및 바이페닐기-카바졸기의 결합 위치가 본 발명의 일 실시상태에 따라 각각 파라 부분에 결합 및 오르토 부분에 결합이 아닌 EB4 내지 EB8을 사용한 비교예 1-4 내지 1-8의 유기 발광 소자 역시 전압상승, 효율저하 및 수명저하 등 실시예에 비해 열화된 특성을 보였다.And, the biphenyl group - the bonding position of the amine group, and the biphenyl group - the bonding position of the carbazole group according to an embodiment of the present invention Comparative Example 1- using EB4 to EB8 that are not bonded to the para portion and not bonded to the ortho portion The organic light emitting devices of 4 to 1-8 also showed deteriorated characteristics compared to the examples such as voltage increase, efficiency decrease, and lifespan decrease.
이상을 통해 본 발명의 바람직한 실시예(전자 차단층)에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고, 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고, 이 또한 발명의 범주에 속한다.Although the preferred embodiment (electron blocking layer) of the present invention has been described above, the present invention is not limited thereto, and it is possible to carry out various modifications within the scope of the claims and detailed description of the invention, This also falls within the scope of the invention.

Claims (15)

  1. 하기 화학식 1로 표시되는 화합물:A compound represented by the following formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2021014328-appb-img-000038
    Figure PCTKR2021014328-appb-img-000038
    상기 화학식 1에 있어서,In Formula 1,
    X는 O 또는 S이고,X is O or S;
    Ar은 치환 또는 비치환된 탄소수 10 내지 30의 알킬기; 치환 또는 비치환된 탄소수 10 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 10 내지 30의 헤테로고리기이고,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,
    L은 직접결합; 또는 치환 또는 비치환된 아릴렌기이고, L is a direct bond; Or a substituted or unsubstituted arylene group,
    R1 내지 R5는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이거나, 또는 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,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 내지 r5는 각각 0 내지 4의 정수이고,r1 to r5 are each an integer of 0 to 4,
    r1 내지 r5가 2 이상인 경우, 괄호 안의 치환기는 서로 같거나 상이하다.When r1 to r5 are 2 or more, the substituents in parentheses are the same as or different from each other.
  2. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 2 내지 5 중 어느 하나로 표시되는 것인 화합물:The method according to claim 1, wherein Formula 1 is a compound represented by any one of Formulas 2 to 5:
    [화학식 2][Formula 2]
    Figure PCTKR2021014328-appb-img-000039
    Figure PCTKR2021014328-appb-img-000039
    [화학식 3][Formula 3]
    Figure PCTKR2021014328-appb-img-000040
    Figure PCTKR2021014328-appb-img-000040
    [화학식 4][Formula 4]
    Figure PCTKR2021014328-appb-img-000041
    Figure PCTKR2021014328-appb-img-000041
    [화학식 5][Formula 5]
    Figure PCTKR2021014328-appb-img-000042
    Figure PCTKR2021014328-appb-img-000042
    상기 화학식 2 내지 5에 있어서, X, Ar, L, R1 내지 R5, 및 r1 내지 r5는 상기 화학식 1에서 정의한 바와 같다.In Formulas 2 to 5, X, Ar, L, R1 to R5, and r1 to r5 are as defined in Formula 1 above.
  3. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 61 내지 63 중 어느 하나로 표시되는 것인 화합물:The compound according to claim 1, wherein Formula 1 is represented by any one of the following Formulas 61 to 63:
    [화학식 61][Formula 61]
    Figure PCTKR2021014328-appb-img-000043
    Figure PCTKR2021014328-appb-img-000043
    [화학식 62][Formula 62]
    Figure PCTKR2021014328-appb-img-000044
    Figure PCTKR2021014328-appb-img-000044
    [화학식 63][Formula 63]
    Figure PCTKR2021014328-appb-img-000045
    Figure PCTKR2021014328-appb-img-000045
    상기 화학식 61 내지 63에 있어서, In Formulas 61 to 63,
    R61 내지 R63은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이고,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 내지 r63은 각각 0 내지 6의 정수이고,r61 to r63 are each an integer of 0 to 6,
    r61 내지 r63이 2 이상인 경우, 괄호 안의 치환기는 서로 같거나 상이하고,When r61 to r63 are 2 or more, the substituents in parentheses are the same as or different from each other,
    X, Ar, L, R1 내지 R4, 및 r1 내지 r4는 상기 화학식 1에서 정의한 바와 같다.X, Ar, L, R1 to R4, and r1 to r4 are as defined in Formula 1 above.
  4. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 71 내지 73 중 어느 하나로 표시되는 것인 화합물:The compound according to claim 1, wherein Formula 1 is represented by any one of the following Formulas 71 to 73:
    [화학식 71][Formula 71]
    Figure PCTKR2021014328-appb-img-000046
    Figure PCTKR2021014328-appb-img-000046
    [화학식 72][Formula 72]
    Figure PCTKR2021014328-appb-img-000047
    Figure PCTKR2021014328-appb-img-000047
    [화학식 73][Formula 73]
    Figure PCTKR2021014328-appb-img-000048
    Figure PCTKR2021014328-appb-img-000048
    상기 화학식 71 내지 73에 있어서, In Formulas 71 to 73,
    R11 내지 R13은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이고,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 내지 r13은 각각 0 내지 6의 정수이고,r11 to r13 are each an integer of 0 to 6,
    r11 내지 r13이 2 이상인 경우, 괄호 안의 치환기는 서로 같거나 상이하고,When r11 to r13 are 2 or more, the substituents in parentheses are the same as or different from each other,
    X, Ar, L, R2 내지 R5, 및 r2 내지 r5는 상기 화학식 1에서 정의한 바와 같다.X, Ar, L, R2 to R5, and r2 to r5 are as defined in Formula 1 above.
  5. 청구항 1에 있어서, R1 및 R2는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라세닐기; 또는 치환 또는 비치환된 페난트레닐기이거나, 또는 인접한 기와 결합하여 치환 또는 비치환된 벤젠 고리를 형성하는 것인 화합물.The method according to claim 1, R1 and R2 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 compound that combines with an adjacent group to form a substituted or unsubstituted benzene ring.
  6. 청구항 1에 있어서, R3 및 R4는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라세닐기; 또는 치환 또는 비치환된 페난트레닐기이거나, 또는 인접한 기와 결합하여 치환 또는 비치환된 벤젠 고리를 형성하는 것인 화합물.The method according to claim 1, R3 and R4 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 compound that combines with an adjacent group to form a substituted or unsubstituted benzene ring.
  7. 청구항 1에 있어서, R5는 수소; 중수소; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라세닐기; 또는 치환 또는 비치환된 페난트레닐기이거나, 또는 인접한 기와 결합하여 치환 또는 비치환된 벤젠 고리를 형성하는 것인 화합물.The method according to claim 1, R5 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 compound that combines with an adjacent group to form a substituted or unsubstituted benzene ring.
  8. 청구항 1에 있어서, L은 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 2가의 바이페닐기; 치환 또는 비치환된 2가의 터페닐기; 치환 또는 비치환된 나프틸렌기; 치환 또는 비치환된 안트라세닐렌기; 또는 치환 또는 비치환된 페난트레닐렌기인 것인 화합물.The method according to claim 1, L 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.
  9. 청구항 1에 있어서, Ar은 치환 또는 비치환된 탄소수 10 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 10 내지 30의 헤테로고리기인 것인 화합물.The method according to claim 1, Ar is a substituted or unsubstituted C10 to C30 aryl group; Or a compound that is a substituted or unsubstituted C10 to C30 heterocyclic group.
  10. 청구항 1에 있어서, Ar은 하기 그룹 1에서 선택되는 어느 하나인 것인 화합물:The compound of claim 1, wherein Ar is any one selected from the following group 1:
    [그룹 1][Group 1]
    Figure PCTKR2021014328-appb-img-000049
    Figure PCTKR2021014328-appb-img-000049
    상기 그룹 1에서 선택된 구조는 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환 또는 비치환되고,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,
    상기 구조에서 점선은 화학식 1의 N에 결합하는 위치를 의미한다.In the structure, the dotted line denotes a position bonded to N in Formula 1.
  11. 청구항 1에 있어서, 상기 화학식 1은 하기 화합물 중에서 선택되는 어느 하나인 것인 화합물:The compound according to claim 1, wherein Formula 1 is any one selected from the following compounds:
    Figure PCTKR2021014328-appb-img-000050
    Figure PCTKR2021014328-appb-img-000050
    Figure PCTKR2021014328-appb-img-000051
    Figure PCTKR2021014328-appb-img-000051
    Figure PCTKR2021014328-appb-img-000052
    Figure PCTKR2021014328-appb-img-000052
    Figure PCTKR2021014328-appb-img-000053
    Figure PCTKR2021014328-appb-img-000053
    Figure PCTKR2021014328-appb-img-000054
    Figure PCTKR2021014328-appb-img-000054
    Figure PCTKR2021014328-appb-img-000055
    Figure PCTKR2021014328-appb-img-000055
    Figure PCTKR2021014328-appb-img-000056
    Figure PCTKR2021014328-appb-img-000056
    Figure PCTKR2021014328-appb-img-000057
    Figure PCTKR2021014328-appb-img-000057
    Figure PCTKR2021014328-appb-img-000058
    .
    Figure PCTKR2021014328-appb-img-000058
    .
  12. 양극; 음극; 및 상기 양극 및 상기 음극 사이에 구비된 유기물층을 포함하고,anode; cathode; and an organic material layer provided between the anode and the cathode,
    상기 유기물층은 청구항 1 내지 11 중 어느 한 항에 따른 화합물을 포함하는 것인 유기 발광 소자.The organic material layer is an organic light emitting device comprising the compound according to any one of claims 1 to 11.
  13. 청구항 12에 있어서,13. The method of claim 12,
    상기 유기물층은 정공 주입층; 정공 수송층; 정공 주입 및 수송층; 및 전자 차단층으로 이루어진 군으로부터 선택되는 1 이상의 층을 포함하는 것인 유기 발광 소자.The organic material layer may include 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.
  14. 청구항 12에 있어서, 13. The method of claim 12,
    상기 유기물층은 전자 차단층을 포함하고, 상기 전자 차단층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound.
  15. 청구항 12에 있어서,13. The method of claim 12,
    상기 유기물층은 발광층; 및The organic material layer may include a light emitting layer; and
    정공 주입층; 정공 수송층; 정공 주입 및 수송층; 및 전자 차단층으로 이루어진 군으로부터 선택되는 1 이상의 층을 포함하고,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,
    상기 정공 주입층; 정공 수송층; 정공 주입 및 수송층; 및 전자 차단층으로 이루어진 군으로부터 선택되는 1 이상의 층은 상기 화합물을 포함하는 것인 유기 발광 소자.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 is an organic light emitting device comprising the compound.
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