WO2020122671A1 - Compound and organic light-emitting device comprising same - Google Patents

Compound and organic light-emitting device comprising same Download PDF

Info

Publication number
WO2020122671A1
WO2020122671A1 PCT/KR2019/017713 KR2019017713W WO2020122671A1 WO 2020122671 A1 WO2020122671 A1 WO 2020122671A1 KR 2019017713 W KR2019017713 W KR 2019017713W WO 2020122671 A1 WO2020122671 A1 WO 2020122671A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
formula
present specification
Prior art date
Application number
PCT/KR2019/017713
Other languages
French (fr)
Korean (ko)
Inventor
김경희
금수정
홍완표
서상덕
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201980016113.1A priority Critical patent/CN111788198B/en
Publication of WO2020122671A1 publication Critical patent/WO2020122671A1/en

Links

Images

Classifications

    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like.
  • the present specification is intended to provide a compound and an organic light emitting device including the same.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent substituents combine to form a substituted or unsubstituted ring,
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r7 is 1 or 2, when 2 R7 is the same or different from each other,
  • r8 is an integer of 1 to 3, and when 2 or more, R8 is the same or different from each other.
  • the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the above-described compound.
  • the compound according to one embodiment of the present specification is used in an organic light emitting device, so that the driving voltage of the organic light emitting device can be lowered, and light efficiency can be improved.
  • the life characteristics of the device can be improved by the thermal stability of the compound.
  • 1 to 3 show an example of an organic light emitting device according to an exemplary embodiment of the present specification.
  • the compound represented by Chemical Formula 1 has a core structure in which benzofuran is condensed in a polycyclic ring in which one cyclohexane ring is condensed in naphthalene, and an arylamine group is connected to the core structure.
  • the cyclohexane ring in the core structure increases the solubility of the substance, facilitating the synthesis of the compound.
  • the luminous efficiency is high because the molecular orientation value is higher than when one cyclohexane ring is condensed and two cyclohexane rings are condensed.
  • the compound represented by Chemical Formula 1 includes two amine groups, and thus has higher luminous efficiency of the device due to increased radiative transition probability (Oscillator strength) compared to a structure that does not contain an amine group or contains one amine group.
  • Cn means n carbon atoms.
  • Cn-Cm means “n to m carbon atoms”.
  • substitution means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and when two or more are substituted , 2 or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; Halogen group; Nitro group; Nitrile group; Alkyl groups; Cycloalkyl group; Amine group; Aryl group; And one or two or more substituents selected from the group consisting of heteroaryl groups containing one or more of N, O, and S atoms, or two or more substituents of the above-exemplified substituents are substituted with linked substituents, or have no substituents.
  • the “substituted or unsubstituted” is deuterium; Halogen group; Nitro group; Nitrile group; C1-C10 alkyl group; C3-C10 cycloalkyl group; Silyl group; Amine group; C6-30 aryl group; And one or more substituents selected from the group consisting of C2-30 heteroaryl groups including one or more of N, O, and S atoms, or substituted with a substituent linked by two or more substituents of the above-described substituents, or It means that it does not have any substituents.
  • examples of the halogen group include fluorine, chlorine, bromine, or iodine.
  • the alkyl group may be straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50, more preferably 1 to 30.
  • Specific examples are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, iso Pentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1- Methylhexyl, cyclopentylmethyl, cyclohexylmethyl, cyclopen
  • the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and more preferably 3 to 30 carbon atoms.
  • an aryl group means a monovalent aromatic hydrocarbon or a monovalent group of an aromatic hydrocarbon derivative.
  • aromatic hydrocarbon means a compound including a ring in which pi electrons are completely conjugated and planar
  • a group derived from aromatic hydrocarbon means a structure in which aromatic hydrocarbon or cyclic aliphatic hydrocarbon is condensed in aromatic hydrocarbon.
  • the aryl group is intended to include a monovalent group in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are connected to each other.
  • the aryl group is not particularly limited, and has 6 to 50 carbon atoms; 6 to 30; 6 to 25; 6 to 20; 6 to 18; Or it is preferably 6 to 13, the aryl group may be monocyclic or polycyclic.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.
  • the substituted fluorenyl group includes all compounds in which the substituents of the pentane ring of fluorene are spiro-bonded to each other to form an aromatic hydrocarbon ring.
  • the substituted fluorenyl group includes 9,9'-spirobifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], etc. However, it is not limited to this.
  • the heteroaryl group is a heteroatom containing one or more of N, O, and S, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms, and more preferably 2 to 30 or 2 to 20 carbon atoms. Do.
  • heteroaryl group examples include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, and acry Din group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, phthalazine, pteridine group, pyrido pyrimidine group, pyrido pyrimidine group pyrazine), pyrazino pyrazine, isoquinoline group, indole group, pyrido indole, indo pyrimidine, 5H-indeno pyrimidine, carbazole group, benzoxazole group, benzimidazole group , Benzothiazole group, benzocarbazole group, benzo
  • an arylene group means one having two bonding positions on the aryl group, that is, a divalent group. These may be applied to the description of the aryl group described above, except that each is a divalent group.
  • the heteroarylene group means a heteroaryl group having two bonding positions, that is, a divalent group. These may be applied to the description of the heteroaryl group described above, except that each is a divalent group.
  • the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted.
  • two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
  • ring is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted hetero ring.
  • the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the cycloalkyl group or aryl group except for the non-monovalent.
  • the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group, except that it is not monovalent.
  • the heterocycle is a non-carbon atom, and contains one or more heteroatoms.
  • the heteroatom may include one or more atoms selected from the group consisting of O, N, and S.
  • the heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the heteroaryl group except that it is not monovalent.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent substituents combine to form a substituted or unsubstituted ring.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Nitrile group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heteroaryl group, or adjacent substituents are combined to form a substituted or unsubstituted C2-C30 ring.
  • R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Nitrile group; A substituted or unsubstituted C1-C5 alkyl group; A substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted C2-C20 heteroaryl group, or adjacent substituents are combined to form a substituted or unsubstituted C2-C30 ring.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A C1-C5 alkyl group unsubstituted or substituted with deuterium; Or a C6-C30 aryl group unsubstituted or substituted with deuterium, or adjacent substituents combine to form a fluorene ring unsubstituted or substituted with deuterium.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A C1-C5 alkyl group unsubstituted or substituted with deuterium; Or a C6-C30 aryl group, or adjacent substituents combine to form a fluorene ring.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; Or it may be a phenyl group, or adjacent substituents may combine to form a fluorene ring.
  • R1 is hydrogen; Or deuterium.
  • R2 is hydrogen; Or deuterium.
  • R1 and R2 are the same as or different from each other.
  • R3 is hydrogen; Or deuterium.
  • R4 is hydrogen; Or deuterium.
  • R3 and R4 combine with each other to form a C2-C20 ring.
  • R3 and R4 are phenyl groups, and combine with each other to form a fluorene ring.
  • R3 and R4 are the same as or different from each other.
  • R5 is hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; Or a phenyl group.
  • R6 is hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; Or a phenyl group.
  • R5 and R6 are the same as or different from each other.
  • R7 and R8 are the same as or different from each other, and each independently hydrogen; Or deuterium.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group with X1; Or a C2-C30 heteroaryl group unsubstituted or substituted with X2.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C20 aryl group with X1; Or a C2-C20 heteroaryl group unsubstituted or substituted with X2.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a monocyclic to 4 ring aryl group substituted or unsubstituted with X1; Or a monocyclic to 5 ring heteroaryl group unsubstituted or substituted with X2.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a monocyclic to 4 ring aryl group substituted or unsubstituted with X1; Or a monocyclic to 4 ring heteroaryl group unsubstituted or substituted with X2.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group with X1; A biphenyl group unsubstituted or substituted with X1; A terphenyl group unsubstituted or substituted with X1; A naphthyl group unsubstituted or substituted with X1; A fluorenyl group unsubstituted or substituted with X1; A benzofluorenyl group unsubstituted or substituted with X1; A carbazole group unsubstituted or substituted with X2; A benzocarbazole group unsubstituted or substituted with X2; A dibenzofuran group unsubstituted or substituted with X2; A naphthobenzofuran group unsubstituted or substituted with X2; A dibenzothiophene group unsubstituted or
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group with X1; A biphenyl group unsubstituted or substituted with X1; A naphthyl group unsubstituted or substituted with X1; A fluorenyl group unsubstituted or substituted with X1; A benzofluorenyl group unsubstituted or substituted with X1; A dibenzofuran group unsubstituted or substituted with X2; A dibenzothiophene group unsubstituted or substituted with X2; A naphthobenzofuran group unsubstituted or substituted with X2; A naphthobenzothiophene group unsubstituted or substituted with X2; Or an indolocarbazole group unsubstituted or substituted with X2.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group with X1; A biphenyl group unsubstituted or substituted with X1; A terphenyl group unsubstituted or substituted with X1; A naphthyl group unsubstituted or substituted with X1; A fluorenyl group unsubstituted or substituted with X1; A dibenzofuran group unsubstituted or substituted with X2; A dibenzothiophene group unsubstituted or substituted with X2; A naphthobenzofuran group unsubstituted or substituted with X2; Or a naphthobenzothiophene group unsubstituted or substituted with X2.
  • Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, halogen group, nitrile group, C1-C5 alkyl group, C3-C10 cycloalkyl group, C6-C20 aryl group And a C6-C20 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of silyl groups or two or more groups selected from the group connected thereto; Or C2-C20 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C1-C5 alkyl group and C3-C10 cycloalkyl group, or two or more groups selected from the group.
  • Ar1 to Ar4 are the same as or different from each other, and each independently, one or more substituents selected from the group consisting of deuterium, halogen groups, and C1-C5 alkyl groups, or two or more groups selected from the group are connected C6-C20 aryl group unsubstituted or substituted with a substituent; Or a C2-C20 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C1-C5 alkyl groups or two or more groups selected from the group.
  • Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, halogen group, nitrile group, C1-C5 alkyl group, or C1-C5 alkyl group substituted with deuterium, substituted with halogen group C1-C5 alkyl group, C3-C10 cycloalkyl group, trimethylsilyl group or dimethylphenylsilyl group substituted or unsubstituted phenyl group; A biphenyl group unsubstituted or substituted with a halogen group, a C1-C5 alkyl group, or a trimethylsilyl group; Terphenyl group; A naphthyl group unsubstituted or substituted with a C1-C5 alkyl group; A fluorenyl group unsubstituted or substituted with a C1-C5 alkyl group; A C1-C5 alkyl group substituted or unsubstit
  • Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, halogen group, nitrile group, alkyl group of C1-C5, alkyl group of C1-C5 substituted with deuterium, or halogen group A substituted or unsubstituted phenyl group with an alkyl group of C1-C5; Biphenyl group; Terphenyl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group; A dibenzofuran group unsubstituted or substituted with a C1-C5 alkyl group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group.
  • Ar1 to Ar4 are the same or different from each other, and each independently deuterium, halogen group, nitrile group, methyl group, tert-butyl group, methyl group substituted with deuterium, trifluoromethyl group, cyclohexyl
  • Ar1 to Ar4 are the same as or different from each other, and each independently substituted with deuterium, a halogen group, a methyl group, a tert-butyl group, a methyl group substituted with deuterium, or a trifluoromethyl group.
  • Ar1 is a substituted or unsubstituted aryl group
  • Ar2 is a substituted or unsubstituted heteroaryl group
  • Ar3 is a substituted or unsubstituted aryl group
  • Ar4 is a substituted or unsubstituted heteroaryl group
  • Ar1 is a substituted or unsubstituted heteroaryl group
  • Ar2 is a substituted or unsubstituted aryl group
  • Ar3 is a substituted or unsubstituted heteroaryl group
  • Ar4 is a substituted or unsubstituted aryl group
  • At least one of Ar1 and Ar2 may be represented by the following Chemical Formula A1.
  • At least one of Ar3 and Ar4 may be represented by the following Chemical Formula A1.
  • Q1 is C(T2)(T3); S; Or O,
  • T1 to T3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with adjacent substituents to form a substituted or unsubstituted ring,
  • t1 is an integer from 0 to 7, and when t1 is 2 or more, T1 is the same as or different from each other.
  • T2 and T3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it is a C1-C5 alkyl group.
  • T2 and T3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a methyl group.
  • T1 is hydrogen; Or deuterium, or two adjacent T1's combine with each other to form a benzene ring.
  • At least one of Ar1 and Ar2 is a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted naphthobenzothiophene group.
  • At least one of the Ar1 and Ar2 is a fluorenyl group unsubstituted or substituted with a methyl group; A benzofluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group or a cyclohexyl group; Dibenzothiophene group; Naphthobenzofuran group; Or a naphthobenzothiophene group.
  • At least one of the Ar1 and Ar2 is a fluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with tert-butyl group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group.
  • At least one of the Ar3 and Ar4 is a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted naphthobenzothiophene group.
  • At least one of the Ar3 and Ar4 is a fluorenyl group unsubstituted or substituted with a methyl group; A benzofluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group or a cyclohexyl group; Dibenzothiophene group; Naphthobenzofuran group; Or a naphthobenzothiophene group.
  • At least one of the Ar3 and Ar4 is a fluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with tert-butyl group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group.
  • Ar1 and Ar3 are the same as each other.
  • Ar2 and Ar4 are the same as each other.
  • Ar1 and Ar2 are the same or different from each other.
  • Ar3 and Ar4 are the same or different from each other.
  • Ar1 to Ar4 are the same as or different from each other, and are any one selected from Groups A or B below.
  • the group A is substituted or unsubstituted by X1
  • the group B is substituted or unsubstituted by X2.
  • X1 and X2 are the same as or different from each other, and each independently, one or more substituents selected from the group consisting of deuterium, halogen groups and C1-C5 alkyl groups, or two or more groups selected from the group are connected It is a substituent.
  • X1 and X2 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; A C1-C5 alkyl group unsubstituted or substituted with deuterium or halogen; C3-C10 cycloalkyl group; A silyl group substituted with a C1-C5 alkyl group or a C6-C20 aryl group; Or it is a C6-C20 aryl group.
  • X1 and X2 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; Methyl group; tert-butyl group; A methyl group substituted with deuterium; A methyl group substituted with a halogen group; Cyclohexyl group; Trimethylsilyl group; It is a dimethylphenylsilyl group.
  • X1 is a deuterium, halogen group, nitrile group, C1-C5 alkyl group, C1-C5 alkyl group substituted with deuterium, C1-C5 alkyl group substituted with halogen group, C3-C10 Cycloalkyl group, trimethylsilyl group or dimethylphenylsilyl group
  • X1 is a deuterium, a halogen group, a nitrile group, a C1-C5 alkyl group, a C1-C5 alkyl group substituted with deuterium, or a C1-C5 alkyl group substituted with a halogen group.
  • X2 is a C1-C5 alkyl group or C3-C10 cycloalkyl group.
  • X2 is a C1-C5 alkyl group.
  • r7 is 1 or 2, and in the case of 2, R7 is the same or different from each other.
  • r7 is 2.
  • r8 is an integer of 1 to 3, and when 2 or more, R8 is the same or different from each other.
  • r8 is 3.
  • -N(Ar1)(Ar2) and -N(Ar3)(Ar4) of Chemical Formula 1 are the same or different from each other.
  • -N(Ar1)(Ar2) and -N(Ar3)(Ar4) of Chemical Formula 1 are the same.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.
  • R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
  • Chemical Formula 1 is represented by Chemical Formula 1-1.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 2-4.
  • R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 3-1 to 3-4.
  • R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 4-1 to 4-4.
  • R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
  • Chemical Formula 1 is represented by the following Chemical Formula 5-1.
  • R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
  • Chemical Formula 1 is represented by the following Chemical Formula 6-1.
  • R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
  • the compound represented by Chemical Formula 1 is any one selected from the following compounds.
  • the compound according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described later. Representative examples are described in the manufacturing examples described below, but if necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, based on techniques known in the art, it is possible to change starting materials, reactants, reaction conditions, and the like.
  • a core structure may be prepared as in the following General Formula 1.
  • Substituents can be combined by methods known in the art, and the type, location, or number of substituents can be changed according to techniques known in the art. Substituents may be bonded as shown in General Formula 1, but are not limited thereto.
  • Ar1 to Ar4, R5 and R6 are the same as defined in Formula 1. Although R1 to R4, R7 and R8 are not indicated in the general formula, R1 to R4, R7 and R8 are substituted or reacted with the product produced by the general formula 1 in a manner known in the art. To R4, R7 and R8.
  • the present specification provides an organic light emitting device comprising the above-described compound.
  • the first electrode A second electrode provided to face the first electrode; And an organic light emitting device including one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound.
  • the'layer' is a meaning compatible with the'film' mainly used in the technical field, and refers to a coating covering a desired area.
  • the size of the'layer' is not limited, and each'layer' may have the same or different sizes. In an exemplary embodiment, the size of the'layer' may be the same as that of the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.
  • the meaning that a specific A material is included in the B layer means i) one or more A materials are included in one B layer, and ii) the B layer is composed of one or more layers, and the A material is a multilayer B All of the layers included in one or more layers are included.
  • the meaning that the specific A material is included in the C layer or the D layer includes i) one or more of the C layers of one or more layers, ii) one or more of the D layers of the one or more layers, or iii ) It means both included in each of the C layer of one or more layers and the D layer of one or more layers.
  • the organic light emitting device may include an additional organic material layer in addition to the light emitting layer.
  • the organic material layer of the organic light emitting device of the present specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like.
  • the structure of the organic light emitting device is not limited thereto, and may include fewer organic layers.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1 as a dopant in the light emitting layer.
  • the organic material layer includes a light emitting layer, the light emitting layer includes a compound represented by Chemical Formula 1, and a light emitting layer including a compound represented by Chemical Formula 1 has a blue color.
  • the organic material layer includes two or more light-emitting layers, and at least one of the two or more light-emitting layers includes a compound represented by Chemical Formula 1.
  • the light emitting layer including the compound represented by Chemical Formula 1 has a blue color, and the light emitting layer not containing the compound represented by Chemical Formula 1 may include a blue, red or green light emitting compound known in the art.
  • the organic light emitting diode according to the exemplary embodiment of the present specification includes a light emitting layer, and the light emitting layer includes a compound represented by Formula 1 and a compound represented by Formula H below.
  • L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R21 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
  • L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C6-C30 arylene group; Or a substituted or unsubstituted C2-C30 heteroarylene group containing N, O, or S.
  • L21 and L22 are the same as or different from each other, and each independently a direct bond; C6-C20arylene group; Or a C2-C20 heteroarylene group containing N, O, or S.
  • the arylene group or heteroarylene group is substituted or unsubstituted with a C1-C10 alkyl group, a C6-C20 aryl group, or a C2-C20 heteroaryl group.
  • L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent dibenzofuran group; Or a substituted or unsubstituted divalent dibenzothiophene group.
  • Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heteroaryl group.
  • Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group with deuterium; Or a C2-C30 heteroaryl group unsubstituted or substituted with deuterium.
  • Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 4 ring aryl group; Or a substituted or unsubstituted monocyclic to 4 ring heteroaryl group.
  • Ar21 and Ar22 are the same or different from each other, and each independently a substituted or unsubstituted deuterium monocyclic to 4 ring aryl group; Or a monocyclic to 4 ring heteroaryl group unsubstituted or substituted with deuterium.
  • Ar21 and Ar22 are the same as or different from each other, and each independently substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted phenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dibenzofur
  • Ar21 and Ar22 are the same as or different from each other, and each independently deuterium, halogen group, nitrile group, C1-C5 alkyl group, C3-C10 cycloalkyl group, or C1-C5 alkyl group.
  • Ar21 and Ar22 are the same as or different from each other, and each independently substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted phenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted
  • Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthryl group; A fluorenyl group unsubstituted or substituted with a methyl group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group, and Ar21 and Ar22 may contain one or more deuterium.
  • Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Dibenzofuran group; Or a naphthobenzofuran group, and Ar21 and Ar22 may include one or more deuterium.
  • Ar21 and Ar22 are different from each other.
  • Ar21 is a substituted or unsubstituted aryl group
  • Ar22 is a substituted or unsubstituted aryl group
  • Ar21 is a substituted or unsubstituted aryl group
  • Ar22 is a substituted or unsubstituted heteroaryl group.
  • Ar21 is an aryl group unsubstituted or substituted with deuterium
  • Ar22 is an aryl group unsubstituted or substituted with deuterium
  • Ar21 is an aryl group unsubstituted or substituted with deuterium
  • Ar22 is a heteroaryl group unsubstituted or substituted with deuterium.
  • R22 is a group represented by -L23-Ar23.
  • R21 to R28 are the same as or different from each other, and each independently hydrogen or deuterium.
  • At least four of R21 to R28 are deuterium, and the rest are hydrogen.
  • R21 to R28 are hydrogen.
  • R21 to R28 are deuterium.
  • the compound represented by Chemical Formula H is any one selected from the following compounds.
  • Chemical Formula H is represented by the following Chemical Formula H-1.
  • L21, L22, R21, R23 to R28, Ar21 and Ar22 are as defined in Formula H,
  • L23 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar23 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • L21 and L22 described above may be applied to L23.
  • Ar23 is a phenyl group unsubstituted or substituted with deuterium; Biphenyl group; Naphthylene group; Anthracene group; Phenanthrene group; Dibenzofuran group; Naphthobenzofuran group; Pyridine group; Or an isoquinoline group.
  • L23 is a direct bond; Phenylene group; Naphthylene group; Or a divalent thiophene group.
  • Ar23 is a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with deuterium; A naphthylene group unsubstituted or substituted with deuterium; Or a dibenzofuran group unsubstituted or substituted with deuterium.
  • L23 is a direct bond; A phenylene group unsubstituted or substituted with deuterium; Or a naphthylene group unsubstituted or substituted with deuterium.
  • the compound represented by Chemical Formula H-1 is any one selected from the following compounds.
  • the organic light emitting device includes a light emitting layer, the light emitting layer includes a compound represented by Formula 1 as a dopant in the light emitting layer, and a compound represented by Formula H as a host of the light emitting layer.
  • the content of the compound represented by Formula 1 is 0.01 parts by weight to 30 parts by weight; 0.1 to 20 parts by weight; Or 0.5 to 10 parts by weight.
  • the emission layer may further include a host material in addition to the compound represented by Chemical Formula H.
  • the host material (mixed host compound) further included may be a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, Pyrimidine derivatives, and the like, but are not limited thereto.
  • the mixing ratio of the compound represented by Formula H and the mixed host compound is 95:5 to 5:95.
  • the light emitting layer including the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula H has a blue color.
  • the organic light emitting diode includes two or more light emitting layers, and at least one of the two or more light emitting layers includes a compound represented by Formula 1 and a compound represented by Formula H.
  • the light emitting layer including the compound represented by Formula 1 and the compound represented by Formula H has a blue color, and the light emitting layer not containing the compound represented by Formula 1 and the compound represented by Formula H is blue known in the art, Red or green luminescent compounds.
  • the organic material layer includes a hole injection layer or a hole transport layer.
  • the organic material layer includes an electron injection layer or an electron transport layer.
  • the organic material layer includes an electron blocking layer.
  • the organic material layer includes a hole blocking layer.
  • the organic light emitting device is a hole injection layer, a hole transport layer. It further includes at least one layer or two or more layers selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; A light emitting layer provided between the first electrode and the second electrode; And two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, and at least one of the two or more organic material layers includes a compound represented by Chemical Formula 1.
  • two or more organic material layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a layer simultaneously performing hole transport and hole injection, and an electron blocking layer.
  • the first electrode is an anode or a cathode.
  • the second electrode is a cathode or an anode.
  • the organic light emitting device may be an organic light emitting device having a structure 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 an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • FIGS. 1 to 3. 1 to 3 illustrate an organic light emitting device and are not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which a first electrode 102, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101.
  • the compound represented by Chemical Formula 1 is included in the light emitting layer.
  • a structure of an organic light emitting device in which a first electrode 102, a hole injection layer 103, a hole transport layer 104, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101 is shown. Is illustrated.
  • the compound represented by Chemical Formula 1 is included in one or more layers of the organic material layer.
  • the compound represented by Chemical Formula 1 is included in one or more of the hole injection layer, the hole transport layer, and the light emitting layer.
  • the first electrode 102, the hole injection layer 103, the hole transport layer 104, the electron blocking layer 105, the light emitting layer 106, the hole blocking layer 107, the electron transport layer on the substrate 101 ( 108), the structure of the organic light emitting device in which the electron injection layer 109 and the second electrode 110 are sequentially stacked is illustrated.
  • the compound represented by Chemical Formula 1 is included in one or more layers of the organic material layer.
  • the compound represented by Chemical Formula 1 is included in at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
  • the organic light emitting device of the present specification may be made of materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a positive electrode is deposited by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. It can be produced by forming and forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode 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 compound represented by the formula (1) or the compound represented by the formula (H) may be formed into 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 application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
  • an organic light emitting device may be made by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate.
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the positive electrode material is usually a material having a large work function to facilitate hole injection 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 Combination of metal and oxide such as Sb;
  • 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 such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof;
  • There is a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the organic light emitting device may include an additional light emitting layer other than the light emitting layer including the compound represented by Chemical Formula 1 or the compound represented by Chemical Formula H.
  • the additional emissive layer can include a host material and a dopant material.
  • the host material may be a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, Pyrimidine derivatives, and the like, but are not limited thereto.
  • Examples of the dopant material include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and periplanene having arylamine groups.
  • 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 are selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamine groups. Substituents are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. Further, examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.
  • the compound represented by Chemical Formula 1 when included in an organic material layer other than the light emitting layer, or when an additional light emitting layer is provided, the light emitting material of the light emitting layer is transported and combined with holes and electrons from the hole transport layer and the electron transport layer, respectively.
  • a material capable of emitting light in the visible light region a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • 8-hydroxyquinoline aluminum complex Alq3
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compound
  • Benzoxazole, benzthiazole and benzimidazole compounds Poly(p-phenylenevinylene) (PPV) polymers
  • Spiro compounds Polyfluorene; And rubrene, but is not limited thereto.
  • the hole injection layer is a layer that receives holes from the electrode. It is preferable that the hole injection material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injection effect for the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of the exciton generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. Also, a material having excellent thin film formation ability is preferred. In addition, it is preferable that the high-occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • HOMO high-occupied molecular orbital
  • the hole injection material include metal porphyrins, oligothiophenes, and arylamine-based organic materials; Hexanitrile hexaaza triphenylene series organics; Quinacridone-based organic matter; Perylene-based organic matter; 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 the holes to the light emitting layer.
  • a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer is preferably a material having high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having conjugated and non-conjugated portions.
  • 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 a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons is preferable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material, as used according to the prior art.
  • a suitable negative electrode material has a low work function and is a conventional material followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.
  • the electron injection layer is a layer that receives electrons from an electrode. It is preferable that the electron injecting agent has an excellent electron transporting ability and an electron receiving effect from the second electrode, and an excellent electron injection effect with respect to the light emitting layer or the light emitting material. In addition, a material that prevents exciton generated in the light emitting layer from moving to the hole injection layer and has excellent thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and derivatives thereof, Metal complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, 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-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc. , But is not limited thereto.
  • the electron blocking layer is a layer capable of improving the life and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer.
  • Known materials can be used without limitation, and can be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and the layer simultaneously performing hole injection and hole transport.
  • the hole blocking layer is a layer that blocks reaching the cathode of the hole, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but are not limited thereto.
  • the organic light emitting device may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,500 ⁇ was put in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • Fischer Co. was used as a detergent
  • distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water.
  • ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying, and then transported to a plasma cleaner.
  • the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.
  • the following chemical formula [HAT-CN] was thermally vacuum-deposited to a thickness of 50 Pa to form a hole injection layer.
  • the following formula [NPB] was vacuum-deposited to a thickness of 1,000 MPa on the hole injection layer to form a hole transport layer.
  • the following formula [HT-A] was vacuum deposited on the hole transport layer to a thickness of 200 Pa to form an electron blocking layer.
  • [BH-1] was vacuum-deposited to a thickness of 300 300 as a light emitting host on the electron blocking layer to form a light emitting layer. While depositing the light emitting layer was used as a blue light emitting dopant 3% by weight of the total weight of the host compound 100%.
  • [TPBI] and the following formula [LiQ] were vacuum-deposited on the light emitting layer at a weight ratio of 1:1 to form a first electron transport layer with a thickness of 200 Pa.
  • [LiF] was vacuum deposited on the first electron transport layer to form a second electron transport layer with a thickness of 100 mm 2. On the second electron transport layer, aluminum was deposited to a thickness of 1,000 mm 2 to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 to 1.0 ⁇ /sec
  • the LiF of the second electron transport layer was 0.3 0.3/sec
  • the aluminum of the negative electrode was maintained at a deposition rate of 2 ⁇ /sec.
  • An organic light-emitting device was manufactured by maintaining 1 ⁇ 10 -7 to 5 ⁇ 10 -8 torr.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound of Table 1 was used as the host and the dopant of the emission layer in Example 1.
  • Compounds 1 to 17 according to an exemplary embodiment of the present invention have two arylamine groups while having a core structure in which a benzofuran is condensed in a polycyclic ring in which one cyclohexane ring is condensed in naphthalene.
  • Compound BD-1 of Comparative Example 1 has only one arylamine group
  • Compound BD-2 of Comparative Example 2 has a core structure in which two cyclohexane rings are condensed in naphthalene.
  • the devices of Examples 1 to 17 using the compound having the structure of Formula 1 have properties of blue high efficiency and long life compared to those of Comparative Examples 1 and 2.

Abstract

The present specification 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 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. The present specification relates to a compound and an organic light emitting device including the same.
본 출원은 2018년 12월 14일 한국특허청에 제출된 한국 특허 출원 제10-2018-0161668호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0161668 filed with the Korean Intellectual Property Office on December 14, 2018, the entire contents of which are incorporated herein.
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, 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 that converts electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween. Here, in order to increase the efficiency and stability of the organic light emitting device, the organic material layer is often composed of a multi-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like. When a voltage is applied between two electrodes in the structure of the organic light emitting device, holes are injected at the anode, and electrons are injected at the cathode, and an exciton is formed when the injected holes meet the electrons. When it falls to the ground again, it glows.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다. The development of new materials for such organic light emitting devices continues to be required.
[선행문헌] 국제 특허 출원 공개 제2003-012890호[Prior literature] International patent application publication No. 2003-012890
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자를 제공하고자 한다.The present specification is intended to provide a compound and an organic light emitting device including the same.
본 명세서는 하기 화학식 1로 표시되는 화합물을 제공한다.The present specification provides a compound represented by Formula 1 below.
[화학식 1][Formula 1]
Figure PCTKR2019017713-appb-I000001
Figure PCTKR2019017713-appb-I000001
상기 화학식 1에 있어서,In Chemical Formula 1,
R1 내지 R8는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트로기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 치환기가 결합하여 치환 또는 비치환된 고리를 형성하고,R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent substituents combine to form a substituted or unsubstituted ring,
Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r7은 1 또는 2이고, 2인 경우 R7은 서로 동일하거나 상이하고,r7 is 1 or 2, when 2 R7 is the same or different from each other,
r8은 1 내지 3의 정수이고, 2 이상인 경우 R8은 서로 동일하거나 상이하다.r8 is an integer of 1 to 3, and when 2 or more, R8 is the same or different from each other.
또한, 본 명세서는 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 전술한 화합물을 포함하는 것인 유기 발광 소자를 제공한다.In addition, the present specification is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the above-described compound.
본 명세서의 일 실시상태에 따른 화합물은 유기 발광 소자에 사용되어, 유기 발광 소자의 구동전압을 낮출 수 있으며, 광효율을 향상시킬 수 있다. 또한, 화합물의 열적 안정성에 의하여 소자의 수명 특성을 향상시킬 수 있다. The compound according to one embodiment of the present specification is used in an organic light emitting device, so that the driving voltage of the organic light emitting device can be lowered, and light efficiency can be improved. In addition, the life characteristics of the device can be improved by the thermal stability of the compound.
도 1 내지 도 3은 본 명세서의 일 실시상태에 따른 유기 발광 소자의 예를 도시한 것이다.1 to 3 show an example of an organic light emitting device according to an exemplary embodiment of the present specification.
[부호의 설명][Description of codes]
101: 기판101: substrate
102: 제1 전극102: first electrode
103: 정공 주입층103: hole injection layer
104: 정공 수송층104: hole transport layer
105: 전자 차단층105: electron blocking layer
106: 발광층106: emitting layer
107: 정공 차단층107: hole blocking layer
108: 전자 수송층108: electron transport layer
109: 전자 주입층109: electron injection layer
110: 제2 전극110: second electrode
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, the present specification will be described in more detail.
본 명세서는 상기 화학식 1로 표시되는 화합물을 제공한다.The present specification provides a compound represented by Chemical Formula 1.
상기 화학식 1로 표시되는 화합물은 나프탈렌에 하나의 시클로헥산 고리가 축합된 다환 고리에 벤조퓨란이 축합된 코어 구조를 갖고 있으며, 코어 구조에 아릴아민기가 연결되어 있다. The compound represented by Chemical Formula 1 has a core structure in which benzofuran is condensed in a polycyclic ring in which one cyclohexane ring is condensed in naphthalene, and an arylamine group is connected to the core structure.
코어 구조 중 시클로헥산 고리는 물질의 용해도를 증가시켜, 화합물의 합성을 용이하게 한다. 또한, 하나의 시클로헥산 고리가 축합되어 두 개의 시클로헥산 고리가 축합된 경우에 비하여 분자 배향 값이 높아 발광 효율이 높다.The cyclohexane ring in the core structure increases the solubility of the substance, facilitating the synthesis of the compound. In addition, the luminous efficiency is high because the molecular orientation value is higher than when one cyclohexane ring is condensed and two cyclohexane rings are condensed.
상기 화학식 1로 표시되는 화합물은 2개의 아민기를 포함함으로써, 아민기를 포함하지 않거나 1개의 아민기를 포함하는 구조에 비하여 복사 전이 확률(Oscillator strength)이 증가되어 소자의 발광 효율이 높다.The compound represented by Chemical Formula 1 includes two amine groups, and thus has higher luminous efficiency of the device due to increased radiative transition probability (Oscillator strength) compared to a structure that does not contain an amine group or contains one amine group.
따라서, 본 발명의 화합물을 유기 발광 소자에 적용하면 발광 효율이 우수하고, 낮은 구동전압, 고효율 및 장수명의 효과가 나타난다.Therefore, when the compound of the present invention is applied to an organic light emitting device, light emission efficiency is excellent, and a low driving voltage, high efficiency, and long life effect are exhibited.
본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of substituents herein are described below, but are not limited thereto.
본 명세서에 있어서, Cn은 탄소수 n개를 의미한다.In the present specification, Cn means n carbon atoms.
본 명세서에 있어서, “Cn-Cm”은 “탄소수 n 내지 m개”를 의미한다.In the present specification, “Cn-Cm” means “n to m carbon atoms”.
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 동일하거나 상이할 수 있다.The term "substitution" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and when two or more are substituted , 2 or more substituents may be the same or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트로기; 니트릴기; 알킬기; 시클로알킬기; 아민기; 아릴기; 및 N, O 및 S 원자 중 1개 이상을 포함하는 헤테로아릴기로 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. The term "substituted or unsubstituted" as used herein refers to deuterium; Halogen group; Nitro group; Nitrile group; Alkyl groups; Cycloalkyl group; Amine group; Aryl group; And one or two or more substituents selected from the group consisting of heteroaryl groups containing one or more of N, O, and S atoms, or two or more substituents of the above-exemplified substituents are substituted with linked substituents, or have no substituents. Means
본 명세서의 일 실시상태에 있어서, 상기 “치환 또는 비치환된”은 중수소; 할로겐기; 니트로기; 니트릴기; C1-C10의 알킬기; C3-C10의 시클로알킬기; 실릴기; 아민기; C6-30의 아릴기; 및 N, O, 및 S 원자 중 1개 이상을 포함하는 C2-30의 헤테로아릴기로 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. In one embodiment of the present specification, the “substituted or unsubstituted” is deuterium; Halogen group; Nitro group; Nitrile group; C1-C10 alkyl group; C3-C10 cycloalkyl group; Silyl group; Amine group; C6-30 aryl group; And one or more substituents selected from the group consisting of C2-30 heteroaryl groups including one or more of N, O, and S atoms, or substituted with a substituent linked by two or more substituents of the above-described substituents, or It means that it does not have any substituents.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬, 또는 요오드가 있다. In the present specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.
본 명세서에 있어서, 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 50인 것이 바람직하고, 1 내지 30이 더욱 바람직하다. 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, t-부틸, sec-부틸, 1-메틸부틸, 1-에틸부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, tert-펜틸, 헥실, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸펜틸, 3,3-디메틸부틸, 2-에틸부틸, 헵틸, n-헵틸, 1-메틸헥실, 시클로펜틸메틸, 시클로헥실메틸, 옥틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸프로필, 1,1-디메틸프로필, 이소헥실, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이에 한정되는 것은 아니다. In the present specification, the alkyl group may be straight chain or branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50, more preferably 1 to 30. Specific examples are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, iso Pentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1- Methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl Propyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5-methylhexyl, and the like, but is not limited thereto.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 3 내지 30이 더욱 바람직하다. 구체적으로, 시클로프로필, 시클로부틸, 시클로펜틸, 3-메틸시클로펜틸, 2,3-디메틸시클로펜틸, 시클로헥실, 3-메틸시클로헥실, 4-메틸시클로헥실, 2,3-디메틸시클로헥실, 3,4,5-트리메틸시클로헥실, 4-tert-부틸시클로헥실, 시클로헵틸, 시클로옥틸 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the cycloalkyl group is not particularly limited, but is preferably 3 to 60 carbon atoms, and more preferably 3 to 30 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3 ,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but is not limited thereto.
본 명세서에 있어서, 아릴기는 1가의 방향족 탄화수소 또는 방향족 탄화수소 유도체의 1가의 기를 의미한다. 본 명세서에 있어서, 방향족 탄화수소는 pi 전자가 완전히 콘쥬게이션되고 평면인 고리를 포함하는 화합물을 의미하며, 방향족 탄화수소에서 유도되는 기란, 방향족 탄화수소에 방향족 탄화수소 또는 고리형 지방족 탄화수소가 축합된 구조를 의미한다. 또한 본 명세서에 있어서, 아릴기는 2 이상의 방향족 탄화수소 또는 방향족 탄화수소의 유도체가 서로 연결된 1가의 기를 포함하고자 한다. 아릴기는 특별히 한정되지 않으나, 탄소수 6 내지 50; 6 내지 30; 6 내지 25; 6 내지 20; 6 내지 18; 또는 6 내지 13인 것이 바람직하며, 상기 아릴기는 단환식 또는 다환식일 수 있다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 트리페닐기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. In this specification, an aryl group means a monovalent aromatic hydrocarbon or a monovalent group of an aromatic hydrocarbon derivative. In the present specification, aromatic hydrocarbon means a compound including a ring in which pi electrons are completely conjugated and planar, and a group derived from aromatic hydrocarbon means a structure in which aromatic hydrocarbon or cyclic aliphatic hydrocarbon is condensed in aromatic hydrocarbon. . In addition, in the present specification, the aryl group is intended to include a monovalent group in which two or more aromatic hydrocarbons or derivatives of aromatic hydrocarbons are connected to each other. The aryl group is not particularly limited, and has 6 to 50 carbon atoms; 6 to 30; 6 to 25; 6 to 20; 6 to 18; Or it is preferably 6 to 13, the aryl group may be monocyclic or polycyclic. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, triphenyl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, etc., but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있으며, 인접한 치환기들이 서로 결합하여 고리를 형성할 수 있다. In the present specification, the fluorenyl group may be substituted, and adjacent substituents may combine with each other to form a ring.
본 명세서에 있어서, 플루오레닐기가 치환될 수 있다고 할 때, 치환된 플루오레닐기는 플루오렌의 5각 고리의 치환기가 서로 스피로 결합하여 방향족 탄화수소고리를 형성하는 화합물까지 모두 포함하는 것이다. 상기 치환된 플루오레닐기는 9,9'-스피로바이플루오렌, 스피로[사이클로펜탄-1,9'-플루오렌], 스피로[벤조[c]플루오렌-7,9-플루오렌] 등을 포함하나, 이에 한정되지 않는다.In the present specification, when it is said that the fluorenyl group may be substituted, the substituted fluorenyl group includes all compounds in which the substituents of the pentane ring of fluorene are spiro-bonded to each other to form an aromatic hydrocarbon ring. The substituted fluorenyl group includes 9,9'-spirobifluorene, spiro[cyclopentane-1,9'-fluorene], spiro[benzo[c]fluorene-7,9-fluorene], etc. However, it is not limited to this.
본 명세서에 있어서, 헤테로아릴기는 이종원자로 N, O 및 S 중 1개 이상을 포함하는 것으로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 60인 것이 바람직하고, 2 내지 30 또는 2 내지 20인 것이 더욱 바람직하다. 헤테로아릴기의 예로는, 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 트리아졸기, 피리딘기, 비피리딘기, 피리미딘기, 트리아진기, 아크리딘기, 피리다진기, 피라진기, 퀴놀린기, 퀴나졸린기, 퀴녹살린기, 프탈라진기(phthalazine), 프테리딘기(pteridine), 피리도 피리미딘기(pyrido pyrimidine), 피리도 피라진기(pyrido pyrazine), 피라지노 피라진기(pyrazino pyrazine), 이소퀴놀린기, 인돌기, 피리도 인돌기(pyrido indole), 인데노 피리미딘(5H-indeno pyrimidine), 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨란기, 디벤조퓨란기, 페난쓰롤린기(phenanthroline), 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기 및 티아디아졸릴기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heteroaryl group is a heteroatom containing one or more of N, O, and S, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms, and more preferably 2 to 30 or 2 to 20 carbon atoms. Do. Examples of the heteroaryl group include thiophene group, furan group, pyrrol group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, and acry Din group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, phthalazine, pteridine group, pyrido pyrimidine group, pyrido pyrimidine group pyrazine), pyrazino pyrazine, isoquinoline group, indole group, pyrido indole, indo pyrimidine, 5H-indeno pyrimidine, carbazole group, benzoxazole group, benzimidazole group , Benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, dibenzofuran group, phenanthroline group, thiazolyl group, isooxazolyl group, oxadiazolyl group and Thiadiazolyl groups, and the like, but are not limited to these.
본 명세서에 있어서, 아릴렌기는 아릴기에 결합 위치가 두 개 있는 것, 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 아릴기의 설명이 적용될 수 있다.In the present specification, an arylene group means one having two bonding positions on the aryl group, that is, a divalent group. These may be applied to the description of the aryl group described above, except that each is a divalent group.
본 명세서에 있어서, 헤테로아릴렌기는 헤테로아릴기에 결합 위치가 두 개 있는 것, 즉 2가기를 의미한다. 이들은 각각 2가기인 것을 제외하고는 전술한 헤테로아릴기의 설명이 적용될 수 있다.In the present specification, the heteroarylene group means a heteroaryl group having two bonding positions, that is, a divalent group. These may be applied to the description of the heteroaryl group described above, except that each is a divalent group.
본 명세서에 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 specification, the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted. Can be. For example, two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
본 명세서에 있어서, 인접한 기가 서로 결합하여 형성되는 치환 또는 비치환된 고리에서, "고리"는 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 의미한다.In the present specification, in a substituted or unsubstituted ring formed by bonding adjacent groups to each other, "ring" is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted hetero ring.
본 명세서에 있어서, 탄화수소고리는 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 상기 1가가 아닌 것을 제외하고 상기 시클로알킬기 또는 아릴기의 예시 중에서 선택될 수 있다.In the present specification, the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the cycloalkyl group or aryl group except for the non-monovalent.
본 명세서에 있어서, 방향족고리는 단환 또는 다환일 수 있으며, 1가가 아닌 것을 제외하고 상기 아릴기의 예시 중에서 선택될 수 있다.In the present specification, the aromatic ring may be monocyclic or polycyclic, and may be selected from examples of the aryl group, except that it is not monovalent.
본 명세서에 있어서, 헤테로고리는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 상기 헤테로고리는 단환 또는 다환일 수 있으며, 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 1가가 아닌 것을 제외하고 상기 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present specification, the heterocycle is a non-carbon atom, and contains one or more heteroatoms. Specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, and S. The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the heteroaryl group except that it is not monovalent.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트로기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 치환기가 결합하여 치환 또는 비치환된 고리를 형성한다.In one embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent substituents combine to form a substituted or unsubstituted ring.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트로기; 니트릴기; 치환 또는 비치환된 C1-C10의 알킬기; 치환 또는 비치환된 C6-C30의 아릴기; 또는 치환 또는 비치환된 C2-C30의 헤테로아릴기이거나, 인접한 치환기가 결합하여 치환 또는 비치환된 C2-C30의 고리를 형성한다.In one embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Nitrile group; A substituted or unsubstituted C1-C10 alkyl group; A substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heteroaryl group, or adjacent substituents are combined to form a substituted or unsubstituted C2-C30 ring.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트로기; 니트릴기; 치환 또는 비치환된 C1-C5의 알킬기; 치환 또는 비치환된 C6-C20의 아릴기; 또는 치환 또는 비치환된 C2-C20의 헤테로아릴기이거나, 인접한 치환기가 결합하여 치환 또는 비치환된 C2-C30의 고리를 형성한다.In one embodiment of the present specification, R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Nitrile group; A substituted or unsubstituted C1-C5 alkyl group; A substituted or unsubstituted C6-C20 aryl group; Or a substituted or unsubstituted C2-C20 heteroaryl group, or adjacent substituents are combined to form a substituted or unsubstituted C2-C30 ring.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R6는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소로 치환 또는 비치환된 C1-C5의 알킬기; 또는 중수소로 치환 또는 비치환된 C6-C30의 아릴기이거나, 인접한 치환기가 결합하여 중수소로 치환 또는 비치환된 플루오렌 고리를 형성한다.In one embodiment of the present specification, R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A C1-C5 alkyl group unsubstituted or substituted with deuterium; Or a C6-C30 aryl group unsubstituted or substituted with deuterium, or adjacent substituents combine to form a fluorene ring unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R6는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소로 치환 또는 비치환된 C1-C5의 알킬기; 또는 C6-C30의 아릴기이거나, 인접한 치환기가 결합하여 플루오렌 고리를 형성한다.In one embodiment of the present specification, R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A C1-C5 alkyl group unsubstituted or substituted with deuterium; Or a C6-C30 aryl group, or adjacent substituents combine to form a fluorene ring.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R6은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소로 치환 또는 비치환된 메틸기; 또는 페닐기이거나, 인접한 치환기가 결합하여 플루오렌 고리를 형성한다.In one embodiment of the present specification, R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; Or it may be a phenyl group, or adjacent substituents may combine to form a fluorene ring.
본 명세서의 일 실시상태에 있어서, 상기 R1은 수소; 또는 중수소이다.In one embodiment of the present specification, R1 is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 있어서, 상기 R2는 수소; 또는 중수소이다.In one embodiment of the present specification, R2 is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하다.In one embodiment of the present specification, R1 and R2 are the same as or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 R3은 수소; 또는 중수소이다.In one embodiment of the present specification, R3 is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 있어서, 상기 R4은 수소; 또는 중수소이다.In one embodiment of the present specification, R4 is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 있어서, 상기 R3 및 R4는 서로 결합하여 C2-C20의 고리를 형성한다.In one embodiment of the present specification, R3 and R4 combine with each other to form a C2-C20 ring.
본 명세서의 일 실시상태에 있어서, 상기 R3 및 R4는 페닐기이고, 서로 결합하여 플루오렌 고리를 형성한다.In one embodiment of the present specification, R3 and R4 are phenyl groups, and combine with each other to form a fluorene ring.
본 명세서의 일 실시상태에 있어서, 상기 R3 및 R4는 서로 동일하거나 상이하다.In one embodiment of the present specification, R3 and R4 are the same as or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 R5는 수소; 중수소; 중수소로 치환 또는 비치환된 메틸기; 또는 페닐기이다.In one embodiment of the present specification, R5 is hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; Or a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 R6은 수소; 중수소; 중수소로 치환 또는 비치환된 메틸기; 또는 페닐기이다.In one embodiment of the present specification, R6 is hydrogen; heavy hydrogen; A methyl group unsubstituted or substituted with deuterium; Or a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 R5 및 R6은 서로 동일하거나 상이하다.In one embodiment of the present specification, R5 and R6 are the same as or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 R7 및 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 또는 중수소이다. In one embodiment of the present specification, R7 and R8 are the same as or different from each other, and each independently hydrogen; Or deuterium.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 X1로 치환 또는 비치환된 C6-C30의 아릴기; 또는 X2로 치환 또는 비치환된 C2-C30의 헤테로아릴기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group with X1; Or a C2-C30 heteroaryl group unsubstituted or substituted with X2.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 X1로 치환 또는 비치환된 C6-C20의 아릴기; 또는 X2로 치환 또는 비치환된 C2-C20의 헤테로아릴기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C20 aryl group with X1; Or a C2-C20 heteroaryl group unsubstituted or substituted with X2.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 X1로 치환 또는 비치환된 단환 내지 4환의 아릴기; 또는 X2로 치환 또는 비치환된 단환 내지 5환의 헤테로아릴기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a monocyclic to 4 ring aryl group substituted or unsubstituted with X1; Or a monocyclic to 5 ring heteroaryl group unsubstituted or substituted with X2.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 X1로 치환 또는 비치환된 단환 내지 4환의 아릴기; 또는 X2로 치환 또는 비치환된 단환 내지 4환의 헤테로아릴기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a monocyclic to 4 ring aryl group substituted or unsubstituted with X1; Or a monocyclic to 4 ring heteroaryl group unsubstituted or substituted with X2.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 X1로 치환 또는 비치환된 페닐기; X1로 치환 또는 비치환된 비페닐기; X1로 치환 또는 비치환된 터페닐기; X1로 치환 또는 비치환된 나프틸기; X1로 치환 또는 비치환된 플루오레닐기; X1로 치환 또는 비치환된 벤조플루오레닐기; X2로 치환 또는 비치환된 카바졸기; X2로 치환 또는 비치환된 벤조카바졸기; X2로 치환 또는 비치환된 디벤조퓨란기; X2로 치환 또는 비치환된 나프토벤조퓨란기; X2로 치환 또는 비치환된 디벤조티오펜기; X2로 치환 또는 비치환된 나프토벤조티오펜기; X2로 치환 또는 비치환된 인돌로카바졸기; X2로 치환 또는 비치환된 피리딘기; X2로 치환 또는 비치환된 피리미딘기; 또는 X2로 치환 또는 비치환된 트리아진기이다. In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group with X1; A biphenyl group unsubstituted or substituted with X1; A terphenyl group unsubstituted or substituted with X1; A naphthyl group unsubstituted or substituted with X1; A fluorenyl group unsubstituted or substituted with X1; A benzofluorenyl group unsubstituted or substituted with X1; A carbazole group unsubstituted or substituted with X2; A benzocarbazole group unsubstituted or substituted with X2; A dibenzofuran group unsubstituted or substituted with X2; A naphthobenzofuran group unsubstituted or substituted with X2; A dibenzothiophene group unsubstituted or substituted with X2; A naphthobenzothiophene group unsubstituted or substituted with X2; An indolocarbazole group unsubstituted or substituted with X2; A pyridine group unsubstituted or substituted with X2; A pyrimidine group unsubstituted or substituted with X2; Or a triazine group unsubstituted or substituted with X2.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 X1로 치환 또는 비치환된 페닐기; X1로 치환 또는 비치환된 비페닐기; X1로 치환 또는 비치환된 나프틸기; X1로 치환 또는 비치환된 플루오레닐기; X1로 치환 또는 비치환된 벤조플루오레닐기; X2로 치환 또는 비치환된 디벤조퓨란기; X2로 치환 또는 비치환된 디벤조티오펜기; X2로 치환 또는 비치환된 나프토벤조퓨란기; X2로 치환 또는 비치환된 나프토벤조티오펜기; 또는 X2로 치환 또는 비치환된 인돌로카바졸기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group with X1; A biphenyl group unsubstituted or substituted with X1; A naphthyl group unsubstituted or substituted with X1; A fluorenyl group unsubstituted or substituted with X1; A benzofluorenyl group unsubstituted or substituted with X1; A dibenzofuran group unsubstituted or substituted with X2; A dibenzothiophene group unsubstituted or substituted with X2; A naphthobenzofuran group unsubstituted or substituted with X2; A naphthobenzothiophene group unsubstituted or substituted with X2; Or an indolocarbazole group unsubstituted or substituted with X2.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 X1로 치환 또는 비치환된 페닐기; X1로 치환 또는 비치환된 비페닐기; X1로 치환 또는 비치환된 터페닐기; X1로 치환 또는 비치환된 나프틸기; X1로 치환 또는 비치환된 플루오레닐기; X2로 치환 또는 비치환된 디벤조퓨란기; X2로 치환 또는 비치환된 디벤조티오펜기; X2로 치환 또는 비치환된 나프토벤조퓨란기; 또는 X2로 치환 또는 비치환된 나프토벤조티오펜기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group with X1; A biphenyl group unsubstituted or substituted with X1; A terphenyl group unsubstituted or substituted with X1; A naphthyl group unsubstituted or substituted with X1; A fluorenyl group unsubstituted or substituted with X1; A dibenzofuran group unsubstituted or substituted with X2; A dibenzothiophene group unsubstituted or substituted with X2; A naphthobenzofuran group unsubstituted or substituted with X2; Or a naphthobenzothiophene group unsubstituted or substituted with X2.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 할로겐기, 니트릴기, C1-C5의 알킬기, C3-C10의 시클로알킬기, C6-C20의 아릴기 및 실릴기로 이루어진 군에서 선택된 하나 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 C6-C20의 아릴기; 또는 중수소, C1-C5의 알킬기 및 C3-C10의 시클로알킬기로 이루어진 군에서 선택된 하나 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 C2-C20의 헤테로아릴기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, halogen group, nitrile group, C1-C5 alkyl group, C3-C10 cycloalkyl group, C6-C20 aryl group And a C6-C20 aryl group substituted or unsubstituted with one or more substituents selected from the group consisting of silyl groups or two or more groups selected from the group connected thereto; Or C2-C20 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, C1-C5 alkyl group and C3-C10 cycloalkyl group, or two or more groups selected from the group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 할로겐기 및 C1-C5의 알킬기로 이루어진 군에서 선택된 하나 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 C6-C20의 아릴기; 또는 중수소 및 C1-C5의 알킬기로 이루어진 군에서 선택된 하나 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 C2-C20의 헤테로아릴기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently, one or more substituents selected from the group consisting of deuterium, halogen groups, and C1-C5 alkyl groups, or two or more groups selected from the group are connected C6-C20 aryl group unsubstituted or substituted with a substituent; Or a C2-C20 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium and C1-C5 alkyl groups or two or more groups selected from the group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고 각각 독립적으로 중수소, 할로겐기, 니트릴기, C1-C5의 알킬기, 중수소로 치환된 C1-C5의 알킬기, 할로겐기로 치환된 C1-C5의 알킬기, C3-C10의 시클로알킬기, 트리메틸실릴기 또는 디메틸페닐실릴기로 치환 또는 비치환된 페닐기; 할로겐기, C1-C5의 알킬기 또는 트리메틸실릴기로 치환 또는 비치환된 비페닐기; 터페닐기; C1-C5의 알킬기로 치환 또는 비치환된 나프틸기; C1-C5의 알킬기로 치환 또는 비치환된 플루오레닐기; C1-C5의 알킬기로 치환 또는 비치환된 벤조플로오레닐기; C1-C5의 알킬기 또는 C3-C10의 시클로알킬기로 치환 또는 비치환된 디벤조퓨란기; 나프토벤조퓨란기; 디벤조티오펜기; 나프토벤조티오펜기; 또는 인돌로카바졸기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, halogen group, nitrile group, C1-C5 alkyl group, or C1-C5 alkyl group substituted with deuterium, substituted with halogen group C1-C5 alkyl group, C3-C10 cycloalkyl group, trimethylsilyl group or dimethylphenylsilyl group substituted or unsubstituted phenyl group; A biphenyl group unsubstituted or substituted with a halogen group, a C1-C5 alkyl group, or a trimethylsilyl group; Terphenyl group; A naphthyl group unsubstituted or substituted with a C1-C5 alkyl group; A fluorenyl group unsubstituted or substituted with a C1-C5 alkyl group; A C1-C5 alkyl group substituted or unsubstituted benzofloorenyl group; A dibenzofuran group unsubstituted or substituted with a C1-C5 alkyl group or a C3-C10 cycloalkyl group; Naphthobenzofuran group; Dibenzothiophene group; Naphthobenzothiophene group; Or indolocarbazole.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고 각각 독립적으로 중수소, 할로겐기, 니트릴기, C1-C5의 알킬기, 중수소로 치환된 C1-C5의 알킬기, 또는 할로겐기로 치환된 C1-C5의 알킬기로 치환 또는 비치환된 페닐기; 비페닐기; 터페닐기; 나프틸기; 메틸기로 치환 또는 비치환된 플루오레닐기; C1-C5의 알킬기로 치환 또는 비치환된 디벤조퓨란기; 나프토벤조퓨란기; 디벤조티오펜기; 또는 나프토벤조티오펜기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently deuterium, halogen group, nitrile group, alkyl group of C1-C5, alkyl group of C1-C5 substituted with deuterium, or halogen group A substituted or unsubstituted phenyl group with an alkyl group of C1-C5; Biphenyl group; Terphenyl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group; A dibenzofuran group unsubstituted or substituted with a C1-C5 alkyl group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고 각각 독립적으로 중수소, 할로겐기, 니트릴기, 메틸기, tert-부틸기, 중수소로 치환된 메틸기, 트리플루오로메틸기, 시클로헥실기, 트리메틸실릴기 또는 디메틸페닐실릴기로 치환 또는 비치환된 페닐기; 할로겐기, tert-부틸기 또는 트리메틸실릴기로 치환 또는 비치환된 비페닐기; 터페닐기; tert-부틸기로 치환 또는 비치환된 나프틸기; 메틸기로 치환 또는 비치환된 플루오레닐기; 메틸기로 치환 또는 비치환된 벤조플로오레닐기; tert-부틸기 또는 시클로헥실기로 치환 또는 비치환된 디벤조퓨란기; 나프토벤조퓨란기; 디벤조티오펜기; 나프토벤조티오펜기; 또는 인돌로카바졸기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same or different from each other, and each independently deuterium, halogen group, nitrile group, methyl group, tert-butyl group, methyl group substituted with deuterium, trifluoromethyl group, cyclohexyl A phenyl group unsubstituted or substituted with a silyl group, a trimethylsilyl group or a dimethylphenylsilyl group; A biphenyl group unsubstituted or substituted with a halogen group, a tert-butyl group, or a trimethylsilyl group; Terphenyl group; a naphthyl group unsubstituted or substituted with tert-butyl group; A fluorenyl group unsubstituted or substituted with a methyl group; A benzofloorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group or a cyclohexyl group; Naphthobenzofuran group; Dibenzothiophene group; Naphthobenzothiophene group; Or indolocarbazole.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고 각각 독립적으로 중수소, 할로겐기, 메틸기, tert-부틸기, 중수소로 치환된 메틸기, 또는 트리플루오로메틸기로 치환 또는 비치환된 페닐기; 비페닐기; 터페닐기; 나프틸기; 메틸기로 치환 또는 비치환된 플루오레닐기; tert-부틸기로 치환 또는 비치환된 디벤조퓨란기; 나프토벤조퓨란기; 디벤조티오펜기; 또는 나프토벤조티오펜기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently substituted with deuterium, a halogen group, a methyl group, a tert-butyl group, a methyl group substituted with deuterium, or a trifluoromethyl group. Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; A fluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with tert-butyl group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1은 치환 또는 비치환된 아릴기이고, 상기 Ar2는 치환 또는 비치환된 헤테로아릴기이다,In one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group, and Ar2 is a substituted or unsubstituted heteroaryl group,
본 명세서의 일 실시상태에 있어서, 상기 Ar3은 치환 또는 비치환된 아릴기이고, 상기 Ar4는 치환 또는 비치환된 헤테로아릴기이다,In one embodiment of the present specification, Ar3 is a substituted or unsubstituted aryl group, and Ar4 is a substituted or unsubstituted heteroaryl group,
본 명세서의 일 실시상태에 있어서, 상기 Ar1은 치환 또는 비치환된 헤테로아릴기이고, 상기 Ar2는 치환 또는 비치환된 아릴기이다,In one embodiment of the present specification, Ar1 is a substituted or unsubstituted heteroaryl group, and Ar2 is a substituted or unsubstituted aryl group,
본 명세서의 일 실시상태에 있어서, 상기 Ar3은 치환 또는 비치환된 헤테로아릴기이고, 상기 Ar4는 치환 또는 비치환된 아릴기이다,In one embodiment of the present specification, Ar3 is a substituted or unsubstituted heteroaryl group, and Ar4 is a substituted or unsubstituted aryl group,
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2 중 적어도 하나는 하기 화학식 A1로 표시될 수 있다. In one embodiment of the present specification, at least one of Ar1 and Ar2 may be represented by the following Chemical Formula A1.
본 명세서의 일 실시상태에 있어서, 상기 Ar3 및 Ar4 중 적어도 하나는 하기 화학식 A1로 표시될 수 있다.In one embodiment of the present specification, at least one of Ar3 and Ar4 may be represented by the following Chemical Formula A1.
[화학식 A1][Formula A1]
Figure PCTKR2019017713-appb-I000002
Figure PCTKR2019017713-appb-I000002
상기 화학식 A1에 있어서, In Chemical Formula A1,
Q1은 C(T2)(T3); S; 또는 O이고,Q1 is C(T2)(T3); S; Or O,
T1 내지 T3는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접한 치환기와 서로 결합하여 치환 또는 비치환된 고리를 형성하며,T1 to T3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with adjacent substituents to form a substituted or unsubstituted ring,
t1은 0 내지 7의 정수이고, t1이 2 이상인 경우 T1는 서로 같거나 상이하다. t1 is an integer from 0 to 7, and when t1 is 2 or more, T1 is the same as or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 T2 및 T3은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 C1-C5의 알킬기이다.In one embodiment of the present specification, T2 and T3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or it is a C1-C5 alkyl group.
본 명세서의 일 실시상태에 있어서, 상기 T2 및 T3은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 메틸기이다.In one embodiment of the present specification, T2 and T3 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a methyl group.
본 명세서의 일 실시상태에 있어서, 상기 T1은 수소; 또는 중수소이거나, 인접한 2개의 T1이 서로 결합하여 벤젠 고리를 형성한다.In one embodiment of the present specification, T1 is hydrogen; Or deuterium, or two adjacent T1's combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2 중 적어도 하나는 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 벤조플루오레닐기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 치환 또는 비치환된 나프토벤조퓨란기; 또는 치환 또는 비치환된 나프토벤조티오펜기이다. According to an exemplary embodiment of the present specification, at least one of Ar1 and Ar2 is a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted naphthobenzothiophene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2 중 적어도 하나는 메틸기로 치환 또는 비치환된 플루오레닐기; 메틸기로 치환 또는 비치환된 벤조플루오레닐기; tert-부틸기 또는 시클로헥실기로 치환 또는 비치환된 디벤조퓨란기; 디벤조티오펜기; 나프토벤조퓨란기; 또는 나프토벤조티오펜기이다. According to an exemplary embodiment of the present specification, at least one of the Ar1 and Ar2 is a fluorenyl group unsubstituted or substituted with a methyl group; A benzofluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group or a cyclohexyl group; Dibenzothiophene group; Naphthobenzofuran group; Or a naphthobenzothiophene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar1 및 Ar2 중 적어도 하나는 메틸기로 치환 또는 비치환된 플루오레닐기; tert-부틸기로 치환 또는 비치환된 디벤조퓨란기; 나프토벤조퓨란기; 디벤조티오펜기; 또는 나프토벤조티오펜기이다.According to an exemplary embodiment of the present specification, at least one of the Ar1 and Ar2 is a fluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with tert-butyl group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar3 및 Ar4 중 적어도 하나는 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 벤조플루오레닐기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 치환 또는 비치환된 나프토벤조퓨란기; 또는 치환 또는 비치환된 나프토벤조티오펜기이다. According to an exemplary embodiment of the present specification, at least one of the Ar3 and Ar4 is a substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted naphthobenzothiophene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar3 및 Ar4 중 적어도 하나는 메틸기로 치환 또는 비치환된 플루오레닐기; 메틸기로 치환 또는 비치환된 벤조플루오레닐기; tert-부틸기 또는 시클로헥실기로 치환 또는 비치환된 디벤조퓨란기; 디벤조티오펜기; 나프토벤조퓨란기; 또는 나프토벤조티오펜기이다.According to an exemplary embodiment of the present specification, at least one of the Ar3 and Ar4 is a fluorenyl group unsubstituted or substituted with a methyl group; A benzofluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with a tert-butyl group or a cyclohexyl group; Dibenzothiophene group; Naphthobenzofuran group; Or a naphthobenzothiophene group.
본 명세서의 일 실시상태에 따르면, 상기 Ar3 및 Ar4 중 적어도 하나는 메틸기로 치환 또는 비치환된 플루오레닐기; tert-부틸기로 치환 또는 비치환된 디벤조퓨란기; 나프토벤조퓨란기; 디벤조티오펜기; 또는 나프토벤조티오펜기이다.According to an exemplary embodiment of the present specification, at least one of the Ar3 and Ar4 is a fluorenyl group unsubstituted or substituted with a methyl group; a dibenzofuran group unsubstituted or substituted with tert-butyl group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar3은 서로 동일하다.In one embodiment of the present specification, Ar1 and Ar3 are the same as each other.
본 명세서의 일 실시상태에 있어서, 상기 Ar2 및 Ar4는 서로 동일하다.In one embodiment of the present specification, Ar2 and Ar4 are the same as each other.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2은 서로 동일하거나 상이하다.In one embodiment of the present specification, Ar1 and Ar2 are the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 Ar3 및 Ar4는 서로 동일하거나 상이하다.In one embodiment of the present specification, Ar3 and Ar4 are the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 하기 그룹 A 또는 B에서 선택된 어느 하나이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are any one selected from Groups A or B below.
[그룹 A][Group A]
Figure PCTKR2019017713-appb-I000003
Figure PCTKR2019017713-appb-I000003
[그룹 B][Group B]
Figure PCTKR2019017713-appb-I000004
Figure PCTKR2019017713-appb-I000004
상기 그룹 A 및 B에 있어서,
Figure PCTKR2019017713-appb-I000005
은 N에 연결되는 위치이며,In groups A and B above,
Figure PCTKR2019017713-appb-I000005
Is a position connected to N,
상기 그룹 A는 X1로 치환 또는 비치환되고, 상기 그룹 B는 X2로 치환 또는 비치환된다.The group A is substituted or unsubstituted by X1, and the group B is substituted or unsubstituted by X2.
본 명세서의 일 실시상태에 있어서, 상기 X1 및 X2는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 할로겐기 및 C1-C5의 알킬기로 이루어진 군에서 선택된 하나 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기이다.In one embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently, one or more substituents selected from the group consisting of deuterium, halogen groups and C1-C5 alkyl groups, or two or more groups selected from the group are connected It is a substituent.
본 명세서의 일 실시상태에 있어서, 상기 X1 및 X2는 서로 동일하거나 상이하고, 각각 독립적으로 중수소; 할로겐기; 니트릴기; 중수소 또는 할로겐기로 치환 또는 비치환된 C1-C5의 알킬기; C3-C10의 시클로알킬기; C1-C5의 알킬기 또는 C6-C20의 아릴기로 치환된 실릴기; 또는 C6-C20의 아릴기이다.In one embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; A C1-C5 alkyl group unsubstituted or substituted with deuterium or halogen; C3-C10 cycloalkyl group; A silyl group substituted with a C1-C5 alkyl group or a C6-C20 aryl group; Or it is a C6-C20 aryl group.
본 명세서의 일 실시상태에 있어서, 상기 X1 및 X2는 서로 동일하거나 상이하고, 각각 독립적으로 중수소; 할로겐기; 니트릴기; 메틸기; tert-부틸기; 중수소로 치환된 메틸기; 할로겐기로 치환된 메틸기; 시클로헥실기; 트리메틸실릴기; 디메틸페닐실릴기이다.In one embodiment of the present specification, X1 and X2 are the same as or different from each other, and each independently deuterium; Halogen group; Nitrile group; Methyl group; tert-butyl group; A methyl group substituted with deuterium; A methyl group substituted with a halogen group; Cyclohexyl group; Trimethylsilyl group; It is a dimethylphenylsilyl group.
본 명세서의 일 실시상태에 있어서, 상기 X1는 중수소, 할로겐기, 니트릴기, C1-C5의 알킬기, 중수소로 치환된 C1-C5의 알킬기, 할로겐기로 치환된 C1-C5의 알킬기, C3-C10의 시클로알킬기, 트리메틸실릴기 또는 디메틸페닐실릴기In one embodiment of the present specification, X1 is a deuterium, halogen group, nitrile group, C1-C5 alkyl group, C1-C5 alkyl group substituted with deuterium, C1-C5 alkyl group substituted with halogen group, C3-C10 Cycloalkyl group, trimethylsilyl group or dimethylphenylsilyl group
본 명세서의 일 실시상태에 있어서, 상기 X1는 중수소, 할로겐기, 니트릴기, C1-C5의 알킬기, 중수소로 치환된 C1-C5의 알킬기, 또는 할로겐기로 치환된 C1-C5의 알킬기이다.In one embodiment of the present specification, X1 is a deuterium, a halogen group, a nitrile group, a C1-C5 alkyl group, a C1-C5 alkyl group substituted with deuterium, or a C1-C5 alkyl group substituted with a halogen group.
본 명세서의 일 실시상태에 있어서, 상기 X2는 C1-C5의 알킬기 또는 C3-C10의 시클로알킬기이다.In one embodiment of the present specification, X2 is a C1-C5 alkyl group or C3-C10 cycloalkyl group.
본 명세서의 일 실시상태에 있어서, 상기 X2는 C1-C5의 알킬기이다.In one embodiment of the present specification, X2 is a C1-C5 alkyl group.
본 명세서의 일 실시상태에 있어서, 상기 r7은 1 또는 2이고, 2인 경우 R7은 서로 동일하거나 상이하다.In one embodiment of the present specification, r7 is 1 or 2, and in the case of 2, R7 is the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 r7은 2이다.In one embodiment of the present specification, r7 is 2.
본 명세서의 일 실시상태에 있어서, 상기 r8은 1 내지 3의 정수이고, 2 이상인 경우 R8은 서로 동일하거나 상이하다.In one embodiment of the present specification, r8 is an integer of 1 to 3, and when 2 or more, R8 is the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 r8은 3이다.In one embodiment of the present specification, r8 is 3.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 -N(Ar1)(Ar2) 및 -N(Ar3)(Ar4)은 서로 동일하거나 상이하다.In one embodiment of the present specification, -N(Ar1)(Ar2) and -N(Ar3)(Ar4) of Chemical Formula 1 are the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 -N(Ar1)(Ar2) 및 -N(Ar3)(Ar4)은 동일하다.In one embodiment of the present specification, -N(Ar1)(Ar2) and -N(Ar3)(Ar4) of Chemical Formula 1 are the same.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 1-1 내지 1-4 중 어느 하나로 표시된다.In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.
[화학식 1-1][Formula 1-1]
Figure PCTKR2019017713-appb-I000006
Figure PCTKR2019017713-appb-I000006
[화학식 1-2][Formula 1-2]
Figure PCTKR2019017713-appb-I000007
Figure PCTKR2019017713-appb-I000007
[화학식 1-3][Formula 1-3]
Figure PCTKR2019017713-appb-I000008
Figure PCTKR2019017713-appb-I000008
[화학식 1-4][Formula 1-4]
Figure PCTKR2019017713-appb-I000009
Figure PCTKR2019017713-appb-I000009
상기 화학식 1-1 내지 1-4에 있어서, In Chemical Formulas 1-1 to 1-4,
R1 내지 R8, Ar1 내지 Ar4, r7 및 r8의 정의는 화학식 1에서 정의한 바와 같다.The definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 상기 화학식 1-1로 표시된다.In one embodiment of the present specification, Chemical Formula 1 is represented by Chemical Formula 1-1.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 2-1 내지 2-4 중 어느 하나로 표시된다.In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 2-4.
[화학식 2-1][Formula 2-1]
Figure PCTKR2019017713-appb-I000010
Figure PCTKR2019017713-appb-I000010
[화학식 2-2][Formula 2-2]
Figure PCTKR2019017713-appb-I000011
Figure PCTKR2019017713-appb-I000011
[화학식 2-3][Formula 2-3]
Figure PCTKR2019017713-appb-I000012
Figure PCTKR2019017713-appb-I000012
[화학식 2-4][Formula 2-4]
Figure PCTKR2019017713-appb-I000013
Figure PCTKR2019017713-appb-I000013
상기 화학식 2-1 내지 2-4에 있어서,In Chemical Formulas 2-1 to 2-4,
R1 내지 R8, Ar1 내지 Ar4, r7 및 r8의 정의는 화학식 1에서 정의한 바와 같다.The definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 3-1 내지 3-4 중 어느 하나로 표시된다.In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 3-1 to 3-4.
[화학식 3-1][Formula 3-1]
Figure PCTKR2019017713-appb-I000014
Figure PCTKR2019017713-appb-I000014
[화학식 3-2][Formula 3-2]
Figure PCTKR2019017713-appb-I000015
Figure PCTKR2019017713-appb-I000015
[화학식 3-3][Formula 3-3]
Figure PCTKR2019017713-appb-I000016
Figure PCTKR2019017713-appb-I000016
[화학식 3-4][Formula 3-4]
Figure PCTKR2019017713-appb-I000017
Figure PCTKR2019017713-appb-I000017
상기 화학식 3-1 내지 3-4에 있어서,In Chemical Formulas 3-1 to 3-4,
R1 내지 R8, Ar1 내지 Ar4, r7 및 r8의 정의는 화학식 1에서 정의한 바와 같다.The definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 4-1 내지 4-4 중 어느 하나로 표시된다.In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 4-1 to 4-4.
[화학식 4-1][Formula 4-1]
Figure PCTKR2019017713-appb-I000018
Figure PCTKR2019017713-appb-I000018
[화학식 4-2][Formula 4-2]
Figure PCTKR2019017713-appb-I000019
Figure PCTKR2019017713-appb-I000019
[화학식 4-3][Formula 4-3]
Figure PCTKR2019017713-appb-I000020
Figure PCTKR2019017713-appb-I000020
[화학식 4-4][Formula 4-4]
Figure PCTKR2019017713-appb-I000021
Figure PCTKR2019017713-appb-I000021
상기 화학식 4-1 내지 4-4에 있어서,In Chemical Formulas 4-1 to 4-4,
R1 내지 R8, Ar1 내지 Ar4, r7 및 r8의 정의는 화학식 1에서 정의한 바와 같다.The definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 5-1로 표시된다.In one embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 5-1.
[화학식 5-1][Formula 5-1]
Figure PCTKR2019017713-appb-I000022
Figure PCTKR2019017713-appb-I000022
상기 화학식 5-1에 있어서,In Chemical Formula 5-1,
R1 내지 R8, Ar1 내지 Ar4, r7 및 r8의 정의는 화학식 1에서 정의한 바와 같다.The definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 6-1로 표시된다.In one embodiment of the present specification, Chemical Formula 1 is represented by the following Chemical Formula 6-1.
[화학식 6-1][Formula 6-1]
Figure PCTKR2019017713-appb-I000023
Figure PCTKR2019017713-appb-I000023
상기 화학식 6-1에 있어서,In Chemical Formula 6-1,
R1 내지 R8, Ar1 내지 Ar4, r7 및 r8의 정의는 화학식 1에서 정의한 바와 같다.The definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화합물 중에서 선택되는 어느 하나이다. In one embodiment of the present specification, the compound represented by Chemical Formula 1 is any one selected from the following compounds.
Figure PCTKR2019017713-appb-I000024
Figure PCTKR2019017713-appb-I000024
Figure PCTKR2019017713-appb-I000025
Figure PCTKR2019017713-appb-I000025
Figure PCTKR2019017713-appb-I000026
Figure PCTKR2019017713-appb-I000026
Figure PCTKR2019017713-appb-I000027
Figure PCTKR2019017713-appb-I000027
Figure PCTKR2019017713-appb-I000028
Figure PCTKR2019017713-appb-I000028
Figure PCTKR2019017713-appb-I000029
Figure PCTKR2019017713-appb-I000029
Figure PCTKR2019017713-appb-I000030
Figure PCTKR2019017713-appb-I000030
Figure PCTKR2019017713-appb-I000031
Figure PCTKR2019017713-appb-I000031
Figure PCTKR2019017713-appb-I000032
Figure PCTKR2019017713-appb-I000032
본 명세서의 일 실시상태에 따른 화합물은 후술하는 제조 방법으로 제조될 수 있다. 후술하는 제조예들에서는 대표적인 예시들을 기재하지만, 필요에 따라, 치환기를 추가하거나 제외할 수 있으며, 치환기의 위치를 변경할 수 있다. 또한, 당기술분야에 알려져 있는 기술을 기초로, 출발물질, 반응물질, 반응 조건 등을 변경할 수 있다. The compound according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described later. Representative examples are described in the manufacturing examples described below, but if necessary, a substituent may be added or excluded, and the position of the substituent may be changed. In addition, based on techniques known in the art, it is possible to change starting materials, reactants, reaction conditions, and the like.
예컨대, 상기 화학식 1로 표시되는 화합물은 일 실시상태에 따르면, 하기 일반식 1과 같이 코어 구조가 제조될 수 있다. 치환기는 당기술분야에 알려져 있는 방법에 의하여 결합될 수 있으며, 치환기의 종류, 위치 또는 개수는 당기술분야에 알려져 있는 기술에 따라 변경될 수 있다. 하기 일반식 1과 같이 치환기를 결합시킬 수 있으나, 이에 한정되는 것은 아니다.For example, according to an exemplary embodiment of the compound represented by Chemical Formula 1, a core structure may be prepared as in the following General Formula 1. Substituents can be combined by methods known in the art, and the type, location, or number of substituents can be changed according to techniques known in the art. Substituents may be bonded as shown in General Formula 1, but are not limited thereto.
[일반식 1][Formula 1]
Figure PCTKR2019017713-appb-I000033
Figure PCTKR2019017713-appb-I000033
상기 일반식 1에 있어서, Ar1 내지 Ar4, R5 및 R6에 대한 정의는 상기 화학식 1에서 정의한 바와 동일하다. 상기 일반식에는 R1 내지 R4, R7 및 R8이 표시되어 있지 않지만, R1 내지 R4, R7 및 R8이 치환된 반응물을 사용하거나 상기 일반식 1에 의하여 생성된 생성물에 당 기술 분야에 알려져 있는 방법으로 R1 내지 R4, R7 및 R8를 치환할 수 있다. In Formula 1, Ar1 to Ar4, R5 and R6 are the same as defined in Formula 1. Although R1 to R4, R7 and R8 are not indicated in the general formula, R1 to R4, R7 and R8 are substituted or reacted with the product produced by the general formula 1 in a manner known in the art. To R4, R7 and R8.
또한, 본 명세서는 상기 전술한 화합물을 포함하는 유기 발광 소자를 제공한다.In addition, the present specification provides an organic light emitting device comprising the above-described compound.
본 명세서의 일 실시상태에 있어서, 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 상기 화합물을 포함하는 것인 유기 발광 소자를 제공한다. In one embodiment of the present specification, the first electrode; A second electrode provided to face the first electrode; And an organic light emitting device including one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound.
본 명세서에서 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.When a member is referred to herein as being “on” another member, this includes not only the case where one member abuts another member, but also the case where another member exists between the two members.
본 명세서에서 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 specification, when a part “includes” a certain component, it means that the component may further include other components, rather than excluding other components, unless otherwise specified.
본 명세서에 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 specification, the'layer' is a meaning compatible with the'film' mainly used in the technical field, and refers to a coating covering a desired area. The size of the'layer' is not limited, and each'layer' may have the same or different sizes. In an exemplary embodiment, the size of the'layer' may be the same as that of the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.
본 명세서에 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 specification, the meaning that a specific A material is included in the B layer means i) one or more A materials are included in one B layer, and ii) the B layer is composed of one or more layers, and the A material is a multilayer B All of the layers included in one or more layers are included.
본 명세서에 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 specification, the meaning that the specific A material is included in the C layer or the D layer includes i) one or more of the C layers of one or more layers, ii) one or more of the D layers of the one or more layers, or iii ) It means both included in each of the C layer of one or more layers and the D layer of one or more layers.
본 명세서에 따른 유기 발광 소자는 상기 발광층 이외에 추가의 유기물층을 포함할 수 있다.The organic light emitting device according to the present specification may include an additional organic material layer in addition to the light emitting layer.
본 명세서의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 차단층, 정공 차단층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, and the like. However, the structure of the organic light emitting device is not limited thereto, and may include fewer organic layers.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함한다. In one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 발광층의 도펀트로서 포함한다.In one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1 as a dopant in the light emitting layer.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함하고, 상기 화학식 1로 표시되는 화합물을 포함한 발광층은 청색을 띤다.In one embodiment of the present specification, the organic material layer includes a light emitting layer, the light emitting layer includes a compound represented by Chemical Formula 1, and a light emitting layer including a compound represented by Chemical Formula 1 has a blue color.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 2층 이상의 발광층을 포함하고, 상기 2층 이상의 발광층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 상기 화학식 1로 표시되는 화합물을 포함한 발광층은 청색을 띠며, 상기 화학식 1로 표시되는 화합물을 포함하지 않은 발광층은 당업계에 알려진 청색, 적색 또는 녹색 발광 화합물을 포함할 수 있다.In one embodiment of the present specification, the organic material layer includes two or more light-emitting layers, and at least one of the two or more light-emitting layers includes a compound represented by Chemical Formula 1. The light emitting layer including the compound represented by Chemical Formula 1 has a blue color, and the light emitting layer not containing the compound represented by Chemical Formula 1 may include a blue, red or green light emitting compound known in the art.
본 명세서의 일 실시상태에 따른 유기 발광 소자는 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물 및 하기 화학식 H로 표시되는 화합물을 포함한다. The organic light emitting diode according to the exemplary embodiment of the present specification includes a light emitting layer, and the light emitting layer includes a compound represented by Formula 1 and a compound represented by Formula H below.
[화학식 H][Formula H]
Figure PCTKR2019017713-appb-I000034
Figure PCTKR2019017713-appb-I000034
상기 화학식 H에 있어서,In the formula H,
L21 및 L22는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R21 내지 R28은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,R21 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar21 및 Ar22는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 L21 및 L22는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이다.In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group.
본 명세서의 일 실시상태에 있어서, 상기 L21 및 L22는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 C6-C30의 아릴렌기; 또는 치환 또는 비치환되고 N, O, 또는 S를 포함하는 C2-C30의 헤테로아릴렌기이다.In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C6-C30 arylene group; Or a substituted or unsubstituted C2-C30 heteroarylene group containing N, O, or S.
본 명세서의 일 실시상태에 있어서, 상기 L21 및 L22는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; C6-C20의 아릴렌기; 또는 N, O, 또는 S를 포함하는 C2-C20의 헤테로아릴렌기이다. 상기 아릴렌기 또는 헤테로아릴렌기는 C1-C10의 알킬기, C6-C20의 아릴기 또는 C2-C20의 헤테로아릴기로 치환되거나 비치환된다. In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; C6-C20arylene group; Or a C2-C20 heteroarylene group containing N, O, or S. The arylene group or heteroarylene group is substituted or unsubstituted with a C1-C10 alkyl group, a C6-C20 aryl group, or a C2-C20 heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 L21 및 L22는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 비페닐렌기; 치환 또는 비치환된 나프틸렌기; 치환 또는 비치환된 2가의 디벤조퓨란기; 또는 치환 또는 비치환된 2가의 디벤조티오펜기이다. In one embodiment of the present specification, L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent dibenzofuran group; Or a substituted or unsubstituted divalent dibenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar21 및 Ar22는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 C6-C30의 아릴기; 또는 치환 또는 비치환된 C2-C30의 헤테로아릴기이다.In one embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar21 및 Ar22는 서로 동일하거나 상이하고, 각각 독립적으로 중수소로 치환 또는 비치환된 C6-C30의 아릴기; 또는 중수소로 치환 또는 비치환된 C2-C30의 헤테로아릴기이다.In one embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group with deuterium; Or a C2-C30 heteroaryl group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 Ar21 및 Ar22는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 단환 내지 4환의 아릴기; 또는 치환 또는 비치환된 단환 내지 4환의 헤테로아릴기이다.In one embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 4 ring aryl group; Or a substituted or unsubstituted monocyclic to 4 ring heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar21 및 Ar22는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 중수소로 단환 내지 4환의 아릴기; 또는 중수소로 치환 또는 비치환된 단환 내지 4환의 헤테로아릴기이다.In one embodiment of the present specification, Ar21 and Ar22 are the same or different from each other, and each independently a substituted or unsubstituted deuterium monocyclic to 4 ring aryl group; Or a monocyclic to 4 ring heteroaryl group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 Ar21 및 Ar22는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 비페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라센기; 치환 또는 비치환된 페난트렌기; 치환 또는 비치환된 페날렌기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 벤조플루오레닐기; 치환 또는 비치환된 퓨란기; 치환 또는 비치환된 티오펜기; 치환 또는 비치환된 카바졸기; 치환 또는 비치환된 벤조카바졸기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 나프토벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 치환 또는 비치환된 나프토벤조티오펜기; 치환 또는 비치환된 피리딘기; 치환 또는 비치환된 피리미딘기; 치환 또는 비치환된 트리아진기; 치환 또는 비치환된 퀴놀린기; 치환 또는 비치환된 이소퀴놀린기; 또는 치환 또는 비치환된 인돌로카바졸기이다.In one embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthrene group; A substituted or unsubstituted phenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted benzocarbazole group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted naphthobenzothiophene group; A substituted or unsubstituted pyridine group; A substituted or unsubstituted pyrimidine group; A substituted or unsubstituted triazine group; A substituted or unsubstituted quinoline group; A substituted or unsubstituted isoquinoline group; Or a substituted or unsubstituted indolocarbazole group.
본 명세서의 일 실시상태에 있어서, 상기 Ar21 및 Ar22는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 할로겐기, 니트릴기, C1-C5의 알킬기, C3-C10의 시클로알킬기, C1-C5의 알킬기로 치환된 실릴기, 또는 C6-C20의 아릴기로 치환 또는 비치환된 페닐기; 중수소, 할로겐기, 니트릴기, C1-C5의 알킬기, C3-C10의 시클로알킬기, C1-C5의 알킬기로 치환된 실릴기, 또는 C6-C20의 아릴기로 치환 또는 비치환된 비페닐기; 중수소, 할로겐기, 니트릴기, C1-C5의 알킬기, C3-C10의 시클로알킬기, C1-C5의 알킬기로 치환된 실릴기, 또는 C6-C20의 아릴기로 치환 또는 비치환된 나프틸렌기; 안트라센기; 페난트렌기; 페날렌기; 중수소, 할로겐기, 니트릴기, C1-C5의 알킬기, C3-C10의 시클로알킬기, C1-C5의 알킬기로 치환된 실릴기, 또는 C6-C20의 아릴기로 치환 또는 비치환된 티오펜기; 디벤조퓨란기; 디벤조티오펜기; 나프토벤조퓨란기; 피리딘기; 이소퀴놀린기; 또는 인돌로[3,2,1-jk]카바졸기이다.In one embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently deuterium, halogen group, nitrile group, C1-C5 alkyl group, C3-C10 cycloalkyl group, or C1-C5 alkyl group. A substituted silyl group or a C6-C20 aryl group-substituted or unsubstituted phenyl group; Deuterium, halogen group, nitrile group, C1-C5 alkyl group, C3-C10 cycloalkyl group, C1-C5 alkyl group-substituted silyl group, or C6-C20 aryl group-substituted or unsubstituted biphenyl group; Deuterium, halogen, nitrile, C1-C5 alkyl, C3-C10 cycloalkyl, C1-C5 alkyl group-substituted silyl group, or C6-C20 aryl group-substituted or unsubstituted naphthylene group; Anthracene group; Phenanthrene group; Phenylene group; Deuterium, halogen group, nitrile group, C1-C5 alkyl group, C3-C10 cycloalkyl group, C1-C5 alkyl group substituted silyl group, or C6-C20 aryl group substituted or unsubstituted thiophene group; Dibenzofuran group; Dibenzothiophene group; Naphthobenzofuran group; Pyridine group; Isoquinoline group; Or indolo[3,2,1-jk]carbazole.
본 명세서의 일 실시상태에 있어서, 상기 Ar21 및 Ar22는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 비페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라센기; 치환 또는 비치환된 페난트릴기; 치환 또는 비치환된 페날렌기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 벤조플루오레닐기; 치환 또는 비치환된 퓨란기; 치환 또는 비치환된 티오펜기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 나프토벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 또는 치환 또는 비치환된 나프토벤조티오펜기이다.In one embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted phenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted naphthobenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar21 및 Ar22는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기; 비페닐기; 터페닐기; 나프틸기; 페난트릴기; 메틸기로 치환 또는 비치환된 플루오레닐기; 디벤조퓨란기; 나프토벤조퓨란기; 디벤조티오펜기; 또는 나프토벤조티오펜기이고, 상기 Ar21 및 Ar22는 1 이상의 중수소를 포함할 수 있다.In one embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthryl group; A fluorenyl group unsubstituted or substituted with a methyl group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or a naphthobenzothiophene group, and Ar21 and Ar22 may contain one or more deuterium.
본 명세서의 일 실시상태에 있어서, 상기 Ar21 및 Ar22는 서로 동일하거나 상이하고, 각각 독립적으로 페닐기; 비페닐기; 터페닐기; 나프틸기; 디벤조퓨란기; 또는 나프토벤조퓨란기이고, 상기 Ar21 및 Ar22는 1 이상의 중수소를 포함할 수 있다.In one embodiment of the present specification, Ar21 and Ar22 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Dibenzofuran group; Or a naphthobenzofuran group, and Ar21 and Ar22 may include one or more deuterium.
본 명세서의 일 실시상태에 있어서, 상기 Ar21 및 Ar22는 서로 상이하다.In one embodiment of the present specification, Ar21 and Ar22 are different from each other.
본 명세서의 일 실시상태에 있어서, 상기 Ar21은 치환 또는 비치환된 아릴기이고, 상기 Ar22는 치환 또는 비치환된 아릴기이다.In one embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar21은 치환 또는 비치환된 아릴기이고, 상기 Ar22는 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, Ar21 is a substituted or unsubstituted aryl group, and Ar22 is a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar21은 중수소로 치환 또는 비치환된 아릴기이고, 상기 Ar22는 중수소로 치환 또는 비치환된 아릴기이다.In one embodiment of the present specification, Ar21 is an aryl group unsubstituted or substituted with deuterium, and Ar22 is an aryl group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서, Ar21은 중수소로 치환 또는 비치환된 아릴기이고, Ar22는 중수소로 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, Ar21 is an aryl group unsubstituted or substituted with deuterium, and Ar22 is a heteroaryl group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서 상기 R22는 -L23-Ar23으로 표시되는 기이다.In one embodiment of the present specification, R22 is a group represented by -L23-Ar23.
본 명세서의 일 실시상태에 있어서, 상기 R21 내지 R28은 서로 동일하거나 상이하고, 각각 독립적으로 수소 또는 중수소이다.In one embodiment of the present specification, R21 to R28 are the same as or different from each other, and each independently hydrogen or deuterium.
본 명세서의 일 실시상태에 있어서, 상기 R21 내지 R28 중 넷 이상은 중수소이고, 나머지는 수소이다. In one embodiment of the present specification, at least four of R21 to R28 are deuterium, and the rest are hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R21 내지 R28은 수소이다.In one embodiment of the present specification, R21 to R28 are hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R21 내지 R28은 중수소이다.In one embodiment of the present specification, R21 to R28 are deuterium.
본 명세서의 일 실시상태에 있어서, 상기 화학식 H로 표시되는 화합물은 하기 화합물 중 선택된 어느 하나이다.In one embodiment of the present specification, the compound represented by Chemical Formula H is any one selected from the following compounds.
Figure PCTKR2019017713-appb-I000035
Figure PCTKR2019017713-appb-I000035
Figure PCTKR2019017713-appb-I000036
Figure PCTKR2019017713-appb-I000036
Figure PCTKR2019017713-appb-I000037
Figure PCTKR2019017713-appb-I000037
Figure PCTKR2019017713-appb-I000038
Figure PCTKR2019017713-appb-I000038
Figure PCTKR2019017713-appb-I000039
Figure PCTKR2019017713-appb-I000039
Figure PCTKR2019017713-appb-I000040
Figure PCTKR2019017713-appb-I000040
Figure PCTKR2019017713-appb-I000041
Figure PCTKR2019017713-appb-I000041
Figure PCTKR2019017713-appb-I000042
Figure PCTKR2019017713-appb-I000042
Figure PCTKR2019017713-appb-I000043
Figure PCTKR2019017713-appb-I000043
본 명세서의 일 실시상태에 있어서, 상기 화학식 H는 하기 화학식 H-1로 표시된다.In one embodiment of the present specification, Chemical Formula H is represented by the following Chemical Formula H-1.
[화학식 H-1][Formula H-1]
Figure PCTKR2019017713-appb-I000044
Figure PCTKR2019017713-appb-I000044
상기 화학식 H-1에 있어서,In the formula H-1,
L21, L22, R21, R23 내지 R28, Ar21 및 Ar22의 정의는 화학식 H에서 정의한 바와 같고,The definitions of L21, L22, R21, R23 to R28, Ar21 and Ar22 are as defined in Formula H,
L23는 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L23 is a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar23은 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Ar23 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar23에는 전술한 Ar21 및 Ar22에 관한 설명이 적용될 수 있다.In an exemplary embodiment of the present specification, the description of Ar21 and Ar22 described above may be applied to the Ar23.
본 명세서의 일 실시상태에 있어서, 상기 L23에는 전술한 L21 및 L22에 관한 설명이 적용될 수 있다.In one embodiment of the present specification, the description of L21 and L22 described above may be applied to L23.
본 명세서의 일 실시상태에 있어서, 상기 Ar23은 중수소로 치환 또는 비치환된 페닐기; 비페닐기; 나프틸렌기; 안트라센기; 페난트렌기; 디벤조퓨란기; 나프토벤조퓨란기; 피리딘기; 또는 이소퀴놀린기이다.In one embodiment of the present specification, Ar23 is a phenyl group unsubstituted or substituted with deuterium; Biphenyl group; Naphthylene group; Anthracene group; Phenanthrene group; Dibenzofuran group; Naphthobenzofuran group; Pyridine group; Or an isoquinoline group.
본 명세서의 일 실시상태에 있어서, 상기 L23은 직접결합; 페닐렌기; 나프틸렌기; 또는 2가의 티오펜기이다.In one embodiment of the present specification, L23 is a direct bond; Phenylene group; Naphthylene group; Or a divalent thiophene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar23은 중수소로 치환 또는 비치환된 페닐기; 중수소로 치환 또는 비치환된 비페닐기; 중수소로 치환 또는 비치환된 나프틸렌기; 또는 중수소로 치환 또는 비치환된 디벤조퓨란기이다.In one embodiment of the present specification, Ar23 is a phenyl group unsubstituted or substituted with deuterium; A biphenyl group unsubstituted or substituted with deuterium; A naphthylene group unsubstituted or substituted with deuterium; Or a dibenzofuran group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 L23은 직접결합; 중수소로 치환 또는 비치환된 페닐렌기; 또는 중수소로 치환 또는 비치환된 나프틸렌기이다.In one embodiment of the present specification, L23 is a direct bond; A phenylene group unsubstituted or substituted with deuterium; Or a naphthylene group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 화학식 H-1로 표시되는 화합물은 하기 화합물 중에서 선택되는 어느 하나이다. In one embodiment of the present specification, the compound represented by Chemical Formula H-1 is any one selected from the following compounds.
Figure PCTKR2019017713-appb-I000045
Figure PCTKR2019017713-appb-I000045
Figure PCTKR2019017713-appb-I000046
Figure PCTKR2019017713-appb-I000046
Figure PCTKR2019017713-appb-I000047
Figure PCTKR2019017713-appb-I000047
본 명세서의 일 실시상태에 따른 유기 발광 소자는 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 발광층의 도펀트로서 포함하고, 상기 화학식 H로 표시되는 화합물을 발광층의 호스트로서 포함한다.The organic light emitting device according to an exemplary embodiment of the present specification includes a light emitting layer, the light emitting layer includes a compound represented by Formula 1 as a dopant in the light emitting layer, and a compound represented by Formula H as a host of the light emitting layer.
본 명세서의 일 실시상태에 있어서, 상기 화학식 H로 표시되는 화합물의 중량 100 중량부 기준으로, 상기 화학식 1로 표시되는 화합물의 함량은 0.01 중량부 내지 30 중량부; 0.1 중량부 내지 20 중량부; 또는 0.5 중량부 내지 10 중량부이다.In one embodiment of the present specification, based on 100 parts by weight of the compound represented by Formula H, the content of the compound represented by Formula 1 is 0.01 parts by weight to 30 parts by weight; 0.1 to 20 parts by weight; Or 0.5 to 10 parts by weight.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 상기 화학식 H로 표시되는 화합물 이외에 호스트 물질을 하나 더 포함할 수 있다. 이때, 더 포함되는 호스트 재료(혼합 호스트 화합물)는 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. In one embodiment of the present specification, the emission layer may further include a host material in addition to the compound represented by Chemical Formula H. At this time, the host material (mixed host compound) further included may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, Pyrimidine derivatives, and the like, but are not limited thereto.
상기 화학식 H로 표시되는 화합물 및 상기 혼합 호스트 화합물의 혼합비는 95:5 내지 5:95 이다.The mixing ratio of the compound represented by Formula H and the mixed host compound is 95:5 to 5:95.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물 및 상기 화학식 H로 표시되는 화합물을 포함한 발광층은 청색을 띤다.In one embodiment of the present specification, the light emitting layer including the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula H has a blue color.
본 명세서의 일 실시상태에 따른 유기 발광 소자는 2층 이상의 발광층을 포함하고, 상기 2층 이상의 발광층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물 및 상기 화학식 H로 표시되는 화합물을 포함한다. 상기 화학식 1로 표시되는 화합물 및 상기 화학식 H로 표시되는 화합물을 포함한 발광층은 청색을 띠며, 상기 화학식 1로 표시되는 화합물 및 상기 화학식 H로 표시되는 화합물을 포함하지 않은 발광층은 당업계에 알려진 청색, 적색 또는 녹색 발광 화합물을 포함할 수 있다.The organic light emitting diode according to the exemplary embodiment of the present specification includes two or more light emitting layers, and at least one of the two or more light emitting layers includes a compound represented by Formula 1 and a compound represented by Formula H. The light emitting layer including the compound represented by Formula 1 and the compound represented by Formula H has a blue color, and the light emitting layer not containing the compound represented by Formula 1 and the compound represented by Formula H is blue known in the art, Red or green luminescent compounds.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 정공 주입층 또는 정공 수송층을 포함한다. In one embodiment of the present specification, the organic material layer includes a hole injection layer or a hole transport layer.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 전자 주입층 또는 전자 수송층을 포함한다. In one embodiment of the present specification, the organic material layer includes an electron injection layer or an electron transport layer.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 전자 차단층을 포함한다. In one embodiment of the present specification, the organic material layer includes an electron blocking layer.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 정공 차단층을 포함한다. In one embodiment of the present specification, the organic material layer includes a hole blocking layer.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 정공 주입층, 정공 수송층. 발광층, 전자 수송층, 전자 주입층, 정공 차단층 및 전자 차단층으로 이루어진 군에서 선택되는 1층 또는 2층 이상을 더 포함한다.In one embodiment of the present specification, the organic light emitting device is a hole injection layer, a hole transport layer. It further includes at least one layer or two or more layers selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층; 및 상기 발광층과 상기 제1 전극 사이, 또는 상기 발광층과 상기 제2 전극 사이에 구비된 2층 이상의 유기물층을 포함하고, 상기 2층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. In one embodiment of the present specification, the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; A light emitting layer provided between the first electrode and the second electrode; And two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, and at least one of the two or more organic material layers includes a compound represented by Chemical Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 2층 이상의 유기물층은 발광층, 정공 수송층, 정공 주입층, 정공 수송과 정공 주입을 동시에 하는 층 및 전자 차단층으로 이루어진 군에서 2 이상이 선택될 수 있다.In one embodiment of the present specification, two or more organic material layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a layer simultaneously performing hole transport and hole injection, and an electron blocking layer.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 양극 또는 음극이다.In one embodiment of the present specification, the first electrode is an anode or a cathode.
본 명세서의 일 실시상태에 있어서, 상기 제2 전극은 음극 또는 양극이다. In one embodiment of the present specification, the second electrode is a cathode or an anode.
본 명세서의 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 one embodiment of the present specification, the organic light emitting device may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다.In one embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
예컨대, 본 명세서의 일 실시상태에 따른 유기 발광 소자의 구조가 도 1 내지 3에 예시되어 있다. 상기 도 1 내지 도 3은 유기 발광 소자를 예시한 것이며 이에 한정되는 것은 아니다. For example, the structure of the organic light emitting device according to the exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3. 1 to 3 illustrate an organic light emitting device and are not limited thereto.
도 1에는 기판(101) 위에 제1 전극(102), 발광층(106) 및 제2 전극(110)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 화학식 1로 표시되는 화합물은 발광층에 포함된다.1 illustrates a structure of an organic light emitting device in which a first electrode 102, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101. The compound represented by Chemical Formula 1 is included in the light emitting layer.
도 2에는 기판(101) 위에 제1 전극(102), 정공 주입층(103), 정공 수송층(104), 발광층(106), 제2 전극(110)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 본 발명의 일 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물은 상기 유기물층 중 1층 이상에 포함된다. 또 하나의 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물은 정공 주입층, 정공 수송층 및 발광층 중 1층 이상에 포함된다.2, a structure of an organic light emitting device in which a first electrode 102, a hole injection layer 103, a hole transport layer 104, a light emitting layer 106, and a second electrode 110 are sequentially stacked on a substrate 101 is shown. Is illustrated. According to an exemplary embodiment of the present invention, the compound represented by Chemical Formula 1 is included in one or more layers of the organic material layer. According to another exemplary embodiment, the compound represented by Chemical Formula 1 is included in one or more of the hole injection layer, the hole transport layer, and the light emitting layer.
도 3에는 기판(101) 위에 제1 전극(102), 정공 주입층(103), 정공 수송층(104), 전자 차단층(105), 발광층(106), 정공 차단층(107), 전자 수송층(108), 전자 주입층(109), 제2 전극(110)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 본 발명의 일 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물은 상기 유기물층 중 1층 이상에 포함된다. 또 하나의 실시상태에 따르면, 상기 화학식 1로 표시되는 화합물은 정공 주입층, 정공 수송층, 전자 차단층, 발광층, 정공 차단층, 전자 수송층 및 전자 주입층 중 1층 이상에 포함된다. 3, the first electrode 102, the hole injection layer 103, the hole transport layer 104, the electron blocking layer 105, the light emitting layer 106, the hole blocking layer 107, the electron transport layer on the substrate 101 ( 108), the structure of the organic light emitting device in which the electron injection layer 109 and the second electrode 110 are sequentially stacked is illustrated. According to an exemplary embodiment of the present invention, the compound represented by Chemical Formula 1 is included in one or more layers of the organic material layer. According to another exemplary embodiment, the compound represented by Chemical Formula 1 is included in at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer.
본 명세서의 유기 발광 소자는 유기물층 중 1층 이상이 상기 화합물, 즉 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. The organic light emitting device of the present specification may be made of materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by Formula 1.
상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. 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.
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 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, 발광층 및 전자 수송층을 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. For example, the organic light emitting device of the present specification can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a positive electrode is deposited by depositing a metal or conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. It can be produced by forming and forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. 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.
또한, 상기 화학식 1로 표시되는 화합물 또는 상기 화학식 H로 표시되는 화합물은 유기 발광 소자의 제조시 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 represented by the formula (1) or the compound represented by the formula (H) may be formed into 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 application method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited thereto.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다. 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to this method, an organic light emitting device may be made by sequentially depositing an organic material layer and a cathode material from a cathode material on a substrate. However, the manufacturing method is not limited thereto.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이다. In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.
또 하나의 실시상태에 있어서, 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다. In another exemplary embodiment, the first electrode is a cathode, and the second electrode is an anode.
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. The positive electrode material is usually a material having a large work function to facilitate hole injection 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 : Combination of metal and oxide such as Sb; 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 such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; There is a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
본 명세서에 따른 유기 발광 소자는 상기 화학식 1로 표시되는 화합물 또는 상기 화학식 H로 표시되는 화합물을 포함하는 발광층 이외의 추가의 발광층을 포함할 수 있다. 추가의 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 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. The organic light emitting device according to the present specification may include an additional light emitting layer other than the light emitting layer including the compound represented by Chemical Formula 1 or the compound represented by Chemical Formula H. The additional emissive layer can include a host material and a dopant material. The host material may be a condensed aromatic ring derivative or a heterocyclic compound. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include dibenzofuran derivatives, ladder-type furan compounds, Pyrimidine derivatives, and the like, but are 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 aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and periplanene having arylamine groups. 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 are selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamine groups. Substituents are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like, but are not limited thereto. Further, examples of the metal complex include an iridium complex and a platinum complex, but are not limited thereto.
본 명세서에서, 상기 화학식 1로 표시되는 화합물이 발광층 이외의 유기물층에 포함되거나, 추가의 발광층이 구비되는 경우, 상기 발광층의 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송 받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 예를 들어, 8-히드록시퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌; 및 루브렌 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, when the compound represented by Chemical Formula 1 is included in an organic material layer other than the light emitting layer, or when an additional light emitting layer is provided, the light emitting material of the light emitting layer is transported and combined with holes and electrons from the hole transport layer and the electron transport layer, respectively. As a material capable of emitting light in the visible light region, a material having good quantum efficiency for fluorescence or phosphorescence is preferable. For example, 8-hydroxyquinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene; And rubrene, 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 HOMO(highest occupied molecular orbital)가 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 injection material has the ability to transport holes and thus has a hole receiving effect from the anode and an excellent hole injection effect for the light emitting layer or the light emitting material. In addition, a material having excellent ability to prevent movement of the exciton generated in the light emitting layer to the electron injection layer or the electron injection material is preferable. Also, a material having excellent thin film formation ability is preferred. In addition, it is preferable that the high-occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrins, oligothiophenes, and arylamine-based organic materials; Hexanitrile hexaaza triphenylene series organics; Quinacridone-based organic matter; Perylene-based organic matter; Polythiophene-based conductive polymers such as anthraquinone and polyaniline, but are not limited thereto.
상기 정공 수송층은 정공 주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층이다. 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수취하여 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 바람직하다. 구체적인 예로는, 아릴아민 계열의 유기물, 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 the holes to the light emitting layer. As the hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the light emitting layer is preferably a material having high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having conjugated and non-conjugated portions.
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. As the electron transport material, a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons is preferable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material, as used according to the prior art. Particularly, a suitable negative electrode material has a low work function and is a conventional material followed by an aluminum layer or a silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.
상기 전자 주입층은 전극으로부터 전자를 수취하는 층이다. 전자 주입물로는 전자를 수송하는 능력이 우수하고, 제2 전극으로부터의 전자 수취 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 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 an electrode. It is preferable that the electron injecting agent has an excellent electron transporting ability and an electron receiving effect from the second electrode, and an excellent electron injection effect with respect to the light emitting layer or the light emitting material. In addition, a material that prevents exciton 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, perylenetetracarboxylic acid, preorenylidene methane, anthrone, and 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-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)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. 공지된 재료는 제한 없이 사용 가능하며, 발광층과 정공 주입층 사이에, 또는 발광층과 정공 주입 및 정공 수송을 동시에 하는 층 사이에 형성될 수 있다. The electron blocking layer is a layer capable of improving the life and efficiency of the device by preventing electrons injected from the electron injection layer from entering the hole injection layer through the light emitting layer. Known materials can be used without limitation, and can be formed between the light emitting layer and the hole injection layer, or between the light emitting layer and the layer simultaneously performing hole injection and hole transport.
상기 정공 차단층은 정공의 음극으로 도달을 저지하는 층으로, 일반적으로 전자 주입층과 동일한 조건으로 형성될 수 있다. 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 reaching the cathode of the hole, and may be generally formed under the same conditions as the electron injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, and the like, but are not limited thereto.
본 명세서에 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 specification may be a front emission type, a back emission type, or a double-sided emission type, depending on the material used.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예 및 비교예 등을 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예 및 비교예는 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 상술하는 실시예 및 비교예에 한정되는 것으로 해석되지 않는다. 본 명세서의 실시예 및 비교예는 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, examples and comparative examples will be described in detail to specifically describe the present specification. However, the examples and comparative examples according to the present specification may be modified in various other forms, and the scope of the present specification is not interpreted to be limited to the examples and comparative examples described below. The examples and comparative examples in the present specification are provided to more fully describe the present specification to those skilled in the art.
[합성예1][Synthesis Example 1]
Figure PCTKR2019017713-appb-I000048
Figure PCTKR2019017713-appb-I000048
질소 분위기하에서 중간체 1-a 20 g, 4-클로로-2-플루오로페닐 보로닉산 1-b [(4-chloro-2-fluorophenyl)boronic acid] 14 g, 탄산 칼륨 [potassium carbonate] 18 g 디옥산 400 mL와 물 100 mL를 넣은 후 테트라키스(트리페닐포스핀)팔라듐(0) [tetrakis(triphenylhosphine)palladium(0)] Pd(PPh3)4 2.2 g을 첨가한 후, 120 oC에서 가열하고 12시간 동안 교반하였다. 반응 종료 후 반응액을 실온까지 냉각시키고, 물과 에틸 아세테이트를 가하여 분액한 후 MgSO4(anhydrous) 처리하여 여과하였다. 여과한 용액을 감압하에서 증류제거하고 재결정(ethylacetate/hexane)으로 정제하여 중간체 1-c 를 18 g 수득하였다. (수율 78%, Mass [M+]=357) Under nitrogen atmosphere, the intermediate 1-a 20 g, 4-chloro-2-fluorophenyl boronic acid 1-b [(4-chloro-2-fluorophenyl)boronic acid] 14 g, potassium carbonate [potassium carbonate] 18 g dioxane After adding 400 mL and 100 mL of water, add 2.2 g of tetrakis(triphenylphosphine)palladium(0) [tetrakis(triphenylhosphine)palladium(0)] Pd(PPh 3 ) 4 , heat at 120 o C Stir for 12 hours. After the reaction was completed, the reaction solution was cooled to room temperature, separated by adding water and ethyl acetate, and filtered through MgSO 4 (anhydrous) treatment. The filtered solution was distilled off under reduced pressure and purified by recrystallization (ethylacetate/hexane) to obtain 18 g of intermediate 1-c. (Yield 78%, Mass [M+]=357)
Figure PCTKR2019017713-appb-I000049
Figure PCTKR2019017713-appb-I000049
질소 분위기하에서 중간체 1-c 18 g 와 탄산칼륨 21 g 을 디메틸포름아마이드 [N-dimethylformamide] 300 mL에 넣고 140 oC에서 1시간동안 교반하여 중간체 1-d를 합성하였다. 반응 종료 후 반응액을 실온까지 냉각시키고, 바로 노나플레이트 플로라이드 [perfluorobutanesulfonyl floride] 9.8 mL를 첨가하여 0.5시간동안 교반하였다. 반응이 완료한 후, 물과 에틸아세테이트를 가하여 분액한 후 MgSO4(anhydrous) 처리하여 여과하였다. 여과한 용액을 감압 하에서 증류제거하고 재결정 (톨루엔/헥산)으로 정제하여 중간체 1-e를 20 g 수득하였다. (수율 65%, Mass [M+]=619)In a nitrogen atmosphere, 18 g of intermediate 1-c and 21 g of potassium carbonate were placed in 300 mL of dimethylformamide [N-dimethylformamide] and stirred at 140 ° C for 1 hour to synthesize intermediate 1-d. After the reaction was completed, the reaction solution was cooled to room temperature, and immediately 9.8 mL of nonaplate fluoride was added and stirred for 0.5 hour. After the reaction was completed, water and ethyl acetate were added and the mixture was separated, followed by treatment with MgSO 4 (anhydrous). The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene/hexane) to obtain 20 g of Intermediate 1-e. (Yield 65%, Mass [M+]=619)
Figure PCTKR2019017713-appb-I000050
Figure PCTKR2019017713-appb-I000050
질소분위기 하에서 중간체 1-e 2.0 g, 아민 A-1 1.9 g, 인산칼륨 [potassium phosphate] 2.0 g을 톨루엔 (30 ml)에 녹인 후, 비스(트리 터트-부틸포스핀)팔라듐(0)[Bis(tri-tert-butylphosphine)palladium(0)] 16 mg를 넣고 120 oC에서 가열하고, 18시간 동안 교반하였다. 반응이 완료되면 반응액을 실온까지 냉각시키고, 물 및 aq.NH4Cl를 가하여 분액한 후 MgSO4(무수) 처리하여 여과하였다. 여과한 용액을 감압하에서 증류제거하고 재결정(헥산/톨루엔)으로 정제하여 화합물 1 1.8 g를 얻었다. (수율 67%, Mass [M+]=846)2.0 g of intermediate 1-e, 1.9 g of amine A-1 and 2.0 g of potassium phosphate were dissolved in toluene (30 ml) under a nitrogen atmosphere, followed by bis(tritert-butylphosphine)palladium(0)[Bis (tri-tert-butylphosphine)palladium(0)] 16 mg was added, heated at 120 o C, and stirred for 18 hours. When the reaction was completed, the reaction solution was cooled to room temperature, and water and aq.NH 4 Cl were added to separate the solution, followed by MgSO 4 (anhydrous) treatment and filtering. The filtered solution was distilled off under reduced pressure and purified by recrystallization (hexane/toluene) to obtain 1.8 g of compound 1. (Yield 67%, Mass [M+]=846)
[합성예 2][Synthesis Example 2]
Figure PCTKR2019017713-appb-I000051
Figure PCTKR2019017713-appb-I000051
상기 합성예 1 의 화합물 1의 합성에서 아민 A-1 대신 A-2 2.8g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 2 2.3g 을 수득하였다. (수율 64 %, Mass [M+]=1134)In the synthesis of compound 1 of Synthesis Example 1, except for using 2.8 g of A-2 instead of amine A-1, it was prepared in the same manner as in the synthesis method of compound 1 to obtain 2.3 g of compound 2. (Yield 64%, Mass [M+]=1134)
[합성예 3][Synthesis Example 3]
Figure PCTKR2019017713-appb-I000052
Figure PCTKR2019017713-appb-I000052
상기 합성예 1 의 화합물 1의 합성에서 아민 A-1 대신 A-3 1.8g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 3 2.2g 을 수득하였다. (수율 73 %, Mass [M+]=631)It was prepared in the same manner as in the synthesis method of Compound 1, except that 1.8 g of A-3 was used instead of amine A-1 in the synthesis of Compound 1 of Synthesis Example 1 to obtain 2.2 g of Compound 3. (Yield 73%, Mass [M+]=631)
[합성예 4][Synthesis Example 4]
Figure PCTKR2019017713-appb-I000053
Figure PCTKR2019017713-appb-I000053
상기 합성예 1 의 화합물 1의 합성에서 아민 A-1 대신 A-4 3.0g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 4 3.1g 을 수득하였다. (수율 74 %, Mass [M+]=886)In the synthesis of Compound 1 of Synthesis Example 1, 3.1 g of Compound 4 was obtained by the same method as the synthesis method of Compound 1, except that 3.0 g of A-4 was used instead of amine A-1. (Yield 74%, Mass [M+]=886)
[합성예 5][Synthesis Example 5]
Figure PCTKR2019017713-appb-I000054
Figure PCTKR2019017713-appb-I000054
상기 합성예 1 의 화합물 1의 합성에서 아민 A-1 대신 A-5 3.2g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 5 3.3g 을 수득하였다. (수율 75 %, Mass [M+]=914)It was prepared in the same manner as in the synthesis method of Compound 1, except that 3.2 g of A-5 was used instead of amine A-1 in the synthesis of Compound 1 of Synthesis Example 1 to obtain 3.3 g of Compound 5. (Yield 75%, Mass [M+]=914)
[합성예 6][Synthesis Example 6]
Figure PCTKR2019017713-appb-I000055
Figure PCTKR2019017713-appb-I000055
상기 합성예 1 의 중간체 1-c의 합성에서 중간체 1-a 대신 2-a 20 g 을 사용한 것을 제외하고 중간체1-c의 합성법과 동일하게 제조하여 중간체 2-c 16 g 을 수득하였다. (수율 70%, Mass [M+]=357)In the synthesis of Intermediate 1-c of Synthesis Example 1, 2-g instead of Intermediate 1-a was prepared in the same manner as in the synthesis of Intermediate 1-c to obtain 16 g of Intermediate 2-c. (Yield 70%, Mass [M+]=357)
상기 합성예 1 의 중간체 1-e의 합성에서 1-c 대신 2-c 16g 을 사용한 것을 제외하고 중간체 1-e의 합성법과 동일하게 제조하여 중간체 2-e 21 g 을 수득하였다. (수율 75 %, Mass [M+]=619)In the synthesis of the intermediate 1-e of Synthesis Example 1, except for using 2-c 16g instead of 1-c, it was prepared in the same manner as the synthesis method of the intermediate 1-e to obtain 21g of the intermediate 2-e. (Yield 75%, Mass [M+]=619)
Figure PCTKR2019017713-appb-I000056
Figure PCTKR2019017713-appb-I000056
상기 합성예 1 의 화합물 1의 합성에서 중간체 1-e 대신 2-e 3.0 g, 아민 A-1 대신 A-6 2.4g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 6 2.8g 을 수득하였다. (수율 78 %, Mass [M+]=757) In the synthesis of compound 1 of Synthesis Example 1, except for using 2-e 3.0 g instead of intermediate 1-e and 2.4 g of A-6 instead of amine A-1, it was prepared in the same manner as in the synthesis method of compound 1 to prepare 2.8 g of compound 6 Obtained. (Yield 78%, Mass [M+]=757)
[합성예 7][Synthesis Example 7]
Figure PCTKR2019017713-appb-I000057
Figure PCTKR2019017713-appb-I000057
상기 합성예 1 의 화합물 1의 합성에서 중간체 1-e 대신 2-e 3.0 g, 아민 A-1 대신 A-4 2.6g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 7 3.2g 을 수득하였다. (수율 84 %, Mass [M+]=801) In the synthesis of compound 1 of Synthesis Example 1, 2-g 3.0 g instead of intermediate 1-e, and 2.6 g of A-4 instead of amine A-1 were prepared in the same manner as in compound 1 to prepare 3.2 g of compound 7 Obtained. (Yield 84%, Mass [M+]=801)
[합성예 8][Synthesis Example 8]
Figure PCTKR2019017713-appb-I000058
Figure PCTKR2019017713-appb-I000058
상기 합성예 1 의 중간체 1-c의 합성에서 중간체 1-a 대신 2-a 20 g 을 사용한 것을 제외하고 중간체1-c의 합성법과 동일하게 제조하여 중간체 2-c 18 g 을 수득하였다. (수율 78%, Mass [M+]=357)In the synthesis of Intermediate 1-c of Synthesis Example 1, 2-g instead of Intermediate 1-a was prepared in the same manner as in the synthesis of Intermediate 1-c to obtain 18 g of Intermediate 2-c. (Yield 78%, Mass [M+]=357)
상기 합성예 1 의 중간체 1-e의 합성에서 1-c 대신 2-c 18g 을 사용한 것을 제외하고 중간체 1-e의 합성법과 동일하게 제조하여 중간체 2-e 18 g 을 수득하였다. (수율 58 %, Mass [M+]=619)In the synthesis of the intermediate 1-e of Synthesis Example 1, except for using 2-c 18g instead of 1-c, it was prepared in the same manner as the synthesis method of the intermediate 1-e to obtain 18g of the intermediate 2-e. (Yield 58%, Mass [M+]=619)
Figure PCTKR2019017713-appb-I000059
Figure PCTKR2019017713-appb-I000059
상기 합성예 1 의 화합물 1의 합성에서 중간체 1-e 대신 3-e 3.0 g, 아민 A-1 대신 A-8 1.7g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 8 2.1g 을 수득하였다. (수율 72 %, Mass [M+]=621) In the synthesis of compound 1 of Synthesis Example 1, 3-g 3.0 g instead of intermediate 1-e, and 1.7 g of A-8 instead of amine A-1 were prepared in the same manner as in compound 1 to prepare 2.1 g of compound 8 Obtained. (Yield 72%, Mass [M+]=621)
[합성예 9][Synthesis Example 9]
Figure PCTKR2019017713-appb-I000060
Figure PCTKR2019017713-appb-I000060
상기 합성예 1 의 화합물 1의 합성에서 중간체 1-e 대신 3-e 5.0g을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 9 5.1g 을 수득하였다. (수율 75 %, Mass [M+]=846) In the synthesis of compound 1 of Synthesis Example 1, except for using 3-e 5.0 g instead of the intermediate 1-e, it was prepared in the same manner as in the synthesis method of Compound 1 to obtain 5.1 g of Compound 9. (Yield 75%, Mass [M+]=846)
[합성예 10][Synthesis Example 10]
Figure PCTKR2019017713-appb-I000061
Figure PCTKR2019017713-appb-I000061
상기 합성예 1 의 화합물 1의 합성에서 중간체 1-e 대신 3-e 3.0 g, 아민 A-1 대신 A-9 3.0g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 10 3.3g 을 수득하였다. (수율 78 %, Mass [M+]=886) In the synthesis of compound 1 of Synthesis Example 1, 3-g 3.0 g instead of intermediate 1-e, and 3.0 g A-9 instead of amine A-1 were prepared in the same manner as in the synthesis method of compound 1 to prepare 3.3 g of compound 10. Obtained. (Yield 78%, Mass [M+]=886)
[합성예 11][Synthesis Example 11]
Figure PCTKR2019017713-appb-I000062
Figure PCTKR2019017713-appb-I000062
상기 합성예 1 의 화합물 1의 합성에서 중간체 1-e 대신 3-e 3.0 g, 아민 A-1 대신 A-3 1.8g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 11 2.3g 을 수득하였다. (수율 77 %, Mass [M+]=631) In the synthesis of compound 1 of Synthesis Example 1, 3-g 3.0 g instead of intermediate 1-e, and 1.8 g of A-3 instead of amine A-1 were prepared in the same manner as in the synthesis method of compound 1 to prepare 2.3 g of compound 11 Obtained. (Yield 77%, Mass [M+]=631)
[합성예 12][Synthesis Example 12]
Figure PCTKR2019017713-appb-I000063
Figure PCTKR2019017713-appb-I000063
상기 합성예 1 의 화합물 1의 합성에서 중간체 1-e 대신 3-e 3.0 g, 아민 A-1 대신 A-10 3.0g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 12 2.1g 을 수득하였다. (수율 70 %, Mass [M+]=886) In the synthesis of compound 1 of Synthesis Example 1, except that 3-e 3.0 g instead of intermediate 1-e and 3.0 g of A-10 instead of amine A-1 were prepared in the same manner as in the synthesis method of compound 1, 2.1 g of compound 12 was prepared. Obtained. (Yield 70%, Mass [M+]=886)
[합성예 13][Synthesis Example 13]
Figure PCTKR2019017713-appb-I000064
Figure PCTKR2019017713-appb-I000064
상기 합성예 1 의 중간체 1-c의 합성에서 중간체 1-a 대신 4-a 20 g 을 사용한 것을 제외하고 중간체1-c의 합성법과 동일하게 제조하여 중간체 4-c 15 g 을 수득하였다. (수율 65%, Mass [M+]=357)In the synthesis of Intermediate 1-c of Synthesis Example 1, except for using 4-a 20 g instead of Intermediate 1-a, 15 g of Intermediate 4-c was obtained in the same manner as in the synthesis method of Intermediate 1-c. (Yield 65%, Mass [M+]=357)
상기 합성예 1 의 중간체 1-e의 합성에서 1-c 대신 4-c 15g 을 사용한 것을 제외하고 중간체 1-e의 합성법과 동일하게 제조하여 중간체 4-e 13 g 을 수득하였다. (수율 50 %, Mass [M+]=619)In the synthesis of Intermediate 1-e of Synthesis Example 1, except that 4-c 15g was used instead of 1-c, the same method as in Intermediate 1-e was obtained to obtain Intermediate 4-e 13g. (Yield 50%, Mass [M+]=619)
Figure PCTKR2019017713-appb-I000065
Figure PCTKR2019017713-appb-I000065
상기 합성예 1 의 화합물 1의 합성에서 중간체 1-e 대신 4-e 3.0 g, 아민 A-1 대신 A-11 2.0g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 13 2.7g 을 수득하였다. (수율 82 %, Mass [M+]=689) In the synthesis of Compound 1 of Synthesis Example 1, except that 4-e 3.0 g instead of Intermediate 1-e and 2.0 g of A-11 instead of amine A-1 were used, the same method as in Synthesis of Compound 1 was carried out to yield 2.7 g of Compound 13 Obtained. (Yield 82%, Mass [M+]=689)
[합성예 14][Synthesis Example 14]
Figure PCTKR2019017713-appb-I000066
Figure PCTKR2019017713-appb-I000066
상기 합성예 1 의 화합물 1의 합성에서 중간체 1-e 대신 3-e 3.0 g, 아민 A-1 대신 A-12 3.0g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 14 3.2g 을 수득하였다. (수율 74 %, Mass [M+]=914) In the synthesis of Compound 1 of Synthesis Example 1, 3-g 3.0 g instead of Intermediate 1-e, and 3.0 g A-12 instead of Amine A-1 were prepared in the same manner as in Synthesis of Compound 1 to prepare 3.2 g of Compound 14 Obtained. (Yield 74%, Mass [M+]=914)
[합성예 15][Synthesis Example 15]
Figure PCTKR2019017713-appb-I000067
Figure PCTKR2019017713-appb-I000067
상기 합성예 1 의 중간체 1-c의 합성에서 중간체 1-a 대신 5-a 10 g 을 사용한 것을 제외하고 중간체1-c의 합성법과 동일하게 제조하여 중간체 5-c 8.4 g 을 수득하였다. (수율 70%, Mass [M+]=363)In the synthesis of Intermediate 1-c of Synthesis Example 1, except for using 5-a 10 g instead of Intermediate 1-a, it was prepared in the same manner as in the synthesis method of Intermediate 1-c to obtain 8.4 g of Intermediate 5-c. (Yield 70%, Mass [M+]=363)
상기 합성예 1 의 중간체 1-e의 합성에서 1-c 대신 5-c 8.4g 을 사용한 것을 제외하고 중간체 1-e의 합성법과 동일하게 제조하여 중간체 5-e 8.5 g 을 수득하였다. (수율 61 %, Mass [M+]=625)In the synthesis of Intermediate 1-e of Synthesis Example 1, except that 5-c 8.4 g instead of 1-c was used, the same method as in Intermediate 1-e was used to obtain 8.5 g of Intermediate 5-e. (Yield 61%, Mass [M+]=625)
Figure PCTKR2019017713-appb-I000068
Figure PCTKR2019017713-appb-I000068
상기 합성예 1 의 화합물 1의 합성에서 중간체 1-e 대신 5-e 3.0 g, 아민 A-1 대신 A-3 2.6g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 15 2.1g 을 수득하였다. (수율 70 %, Mass [M+]=637) In the synthesis of compound 1 of Synthesis Example 1, except for using 5-e 3.0 g instead of intermediate 1-e and 2.6 g of A-3 instead of amine A-1, it was prepared in the same manner as in the synthesis method of compound 1 to produce 2.1 g of compound 15. Obtained. (Yield 70%, Mass [M+]=637)
[합성예 16][Synthesis Example 16]
Figure PCTKR2019017713-appb-I000069
Figure PCTKR2019017713-appb-I000069
상기 합성예 1 의 중간체 1-c의 합성에서 중간체 1-a 대신 6-a 10 g 을 사용한 것을 제외하고 중간체1-c의 합성법과 동일하게 제조하여 중간체 6-c 8.0 g 을 수득하였다. (수율 73%, Mass [M+]=481)In the synthesis of Intermediate 1-c of Synthesis Example 1, except for using 6-a 10 g instead of Intermediate 1-a, it was prepared in the same manner as the synthesis method of Intermediate 1-c to obtain 8.0 g of Intermediate 6-c. (Yield 73%, Mass [M+]=481)
상기 합성예 1 의 중간체 1-e의 합성에서 1-c 대신 6-c 8.0g 을 사용한 것을 제외하고 중간체 1-e의 합성법과 동일하게 제조하여 중간체 6-e 7.6 g 을 수득하였다. (수율 63 %, Mass [M+]=744)In the synthesis of Intermediate 1-e of Synthesis Example 1, except that 6-c 8.0g instead of 1-c was used, the same method as for Intermediate 1-e was used to obtain 7.6 g of Intermediate 6-e. (Yield 63%, Mass [M+]=744)
Figure PCTKR2019017713-appb-I000070
Figure PCTKR2019017713-appb-I000070
상기 합성예 1 의 화합물 1의 합성에서 중간체 1-e 대신 6-e 3.0 g, 아민 A-1 대신 A-13 1.9g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 16 2.7g 을 수득하였다. (수율 79 %, Mass [M+]=858) In the synthesis of Compound 1 of Synthesis Example 1, 6-e 3.0 g instead of Intermediate 1-e, and 1.9 g A-13 instead of Amine A-1 were prepared in the same manner as in Synthesis of Compound 1 to produce 2.7 g of Compound 16. Obtained. (Yield 79%, Mass [M+]=858)
[합성예 17][Synthesis Example 17]
Figure PCTKR2019017713-appb-I000071
Figure PCTKR2019017713-appb-I000071
상기 합성예 1 의 중간체 1-c의 합성에서 중간체 1-a 대신 7-a 5.0 g 을 사용한 것을 제외하고 중간체1-c의 합성법과 동일하게 제조하여 중간체 7-c 4.5 g 을 수득하였다. (수율 80%, Mass [M+]=479)In the synthesis of Intermediate 1-c of Synthesis Example 1, except for using 5.0 g of 7-a instead of Intermediate 1-a, it was prepared in the same manner as the synthesis method of Intermediate 1-c to obtain 4.5 g of Intermediate 7-c. (Yield 80%, Mass [M+]=479)
상기 합성예 1 의 중간체 1-e의 합성에서 1-c 대신 7-c 4.5g 을 사용한 것을 제외하고 중간체 1-e의 합성법과 동일하게 제조하여 중간체 7-e 4.2g 을 수득하였다. (수율 61%, Mass [M+]=742)In the synthesis of Intermediate 1-e of Synthesis Example 1, except for using 7-c 4.5g instead of 1-c, it was prepared in the same manner as in the synthesis method of Intermediate 1-e to obtain 4.2g of Intermediate 7-e. (Yield 61%, Mass [M+]=742)
Figure PCTKR2019017713-appb-I000072
Figure PCTKR2019017713-appb-I000072
상기 합성예 1 의 화합물 1의 합성에서 중간체 1-e 대신 7-e 3.0 g, 아민 A-1 대신 A-8 1.4g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일하게 제조하여 화합물 17 2.3g 을 수득하였다. (수율 77 %, Mass [M+]=743) In the synthesis of Compound 1 of Synthesis Example 1, 7-e 3.0 g instead of Intermediate 1-e, and 1.4 g A-8 instead of Amine A-1 were prepared in the same manner as in Synthesis of Compound 1 to prepare 2.3 g of Compound 17. Obtained. (Yield 77%, Mass [M+]=743)
실시예 1Example 1
ITO(indium tin oxide)가 1,500Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척 하였다. 이 때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀리포어사(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 a thin film of ITO (indium tin oxide) at a thickness of 1,500 Å was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, Fischer Co. was used as a detergent, and distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic washing was repeated for 10 minutes by repeating it twice with distilled water. After washing with distilled water, ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying, and then transported to a plasma cleaner. In addition, the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에 하기 화학식 [HAT-CN]을 50Å의 두께로 열 진공증착하여 정공주입층을 형성하였다. 상기 정공주입층 위에 하기 화학식 [NPB]를 1,000Å의 두께로 진공 증착하여 정공수송층을 형성하였다. 상기 정공수송층 위에 하기 화학식 [HT-A]를 200 Å의 두께로 진공 증착하여 전자차단층을 형성하였다. On the ITO transparent electrode prepared as above, the following chemical formula [HAT-CN] was thermally vacuum-deposited to a thickness of 50 Pa to form a hole injection layer. The following formula [NPB] was vacuum-deposited to a thickness of 1,000 MPa on the hole injection layer to form a hole transport layer. The following formula [HT-A] was vacuum deposited on the hole transport layer to a thickness of 200 Pa to form an electron blocking layer.
이어서, 상기 전자차단층 위에 발광 호스트로 [BH-1]을 300 Å의 두께로 진공 증착하여 발광층을 형성하였다. 상기 발광층을 증착하면서 청색 발광 도펀트로 화합물 1을 호스트 총 중량 100% 대비 3 중량% 사용하였다. 상기 발광층 위에 [TPBI] 및 하기 화학식 [LiQ] 를 1:1 중량비로 진공증착하여 200Å의 두께로 제1 전자수송층을 형성하였다. 상기 제1 전자수송층 위에 [LiF]을 진공 증착하여 100Å의 두께로 제2 전자수송층을 형성하였다. 상기 제2 전자수송층 위에 1,000Å 두께로 알루미늄을 증착하여 음극을 형성하였다. Subsequently, [BH-1] was vacuum-deposited to a thickness of 300 300 as a light emitting host on the electron blocking layer to form a light emitting layer. While depositing the light emitting layer was used as a blue light emitting dopant 3% by weight of the total weight of the host compound 100%. [TPBI] and the following formula [LiQ] were vacuum-deposited on the light emitting layer at a weight ratio of 1:1 to form a first electron transport layer with a thickness of 200 Pa. [LiF] was vacuum deposited on the first electron transport layer to form a second electron transport layer with a thickness of 100 mm 2. On the second electron transport layer, aluminum was deposited to a thickness of 1,000 mm 2 to form a cathode.
상기의 과정에서 유기물의 증착속도는 0.4 ~ 1.0 Å/sec를 유지하였고, 제2 전자수송층의 LiF는 0.3 Å/sec, 음극의 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 1 Х 10-7~ 5 Х 10-8 torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of the organic material was maintained at 0.4 to 1.0 Å/sec, the LiF of the second electron transport layer was 0.3 0.3/sec, and the aluminum of the negative electrode was maintained at a deposition rate of 2 Å/sec. An organic light-emitting device was manufactured by maintaining 1 Х 10 -7 to 5 Х 10 -8 torr.
Figure PCTKR2019017713-appb-I000073
Figure PCTKR2019017713-appb-I000073
실시예 2 내지 17 및 비교예 1 및 2Examples 2 to 17 and Comparative Examples 1 and 2
상기 실시예 1에서 발광층의 호스트 및 도펀트를 하기 표 1의 화합물을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound of Table 1 was used as the host and the dopant of the emission layer in Example 1.
Figure PCTKR2019017713-appb-I000074
Figure PCTKR2019017713-appb-I000074
Figure PCTKR2019017713-appb-I000075
Figure PCTKR2019017713-appb-I000075
Figure PCTKR2019017713-appb-I000076
Figure PCTKR2019017713-appb-I000076
상기에서 실시예 1 내지 17 및 비교예 1 및 2에서 제조된 유기 발광 소자의 10 mA/㎠의 전류밀도에서의 효율, 수명 및 전압을 측정하여, 그 결과를 하기 표 1에 나타내었다.The efficiency, life, and voltage at current densities of 10 mA/cm 2 of the organic light emitting devices manufactured in Examples 1 to 17 and Comparative Examples 1 and 2 were measured above, and the results are shown in Table 1 below.
호스트Host 도펀트Dopant 발광효율(Cd/A)Luminous efficiency (Cd/A) 수명, T95(h)Life, T95(h)
실시예 1Example 1 BH-1BH-1 화합물 1Compound 1 6.646.64 164164
실시예 2Example 2 BH-1BH-1 화합물 2Compound 2 6.556.55 159159
실시예 3Example 3 BH-1BH-1 화합물 3Compound 3 6.526.52 162162
실시예 4Example 4 BH-1BH-1 화합물 4Compound 4 6.486.48 162162
실시예 5Example 5 BH-1BH-1 화합물 5Compound 5 6.446.44 160160
실시예 6Example 6 BH-2BH-2 화합물 6Compound 6 6.386.38 156156
실시예 7Example 7 BH-2BH-2 화합물 7Compound 7 6.416.41 160160
실시예 8Example 8 BH-2BH-2 화합물 8Compound 8 6.356.35 162162
실시예 9Example 9 BH-2BH-2 화합물 9Compound 9 6.526.52 166166
실시예 10Example 10 BH-2BH-2 화합물 10Compound 10 6.506.50 164164
실시예 11Example 11 BH-2BH-2 화합물 11Compound 11 6.426.42 168168
실시예 12Example 12 BH-2BH-2 화합물 12Compound 12 6.406.40 160160
실시예 13Example 13 BH-3BH-3 화합물 13Compound 13 6.266.26 164164
실시예 14Example 14 BH-3BH-3 화합물 14Compound 14 6.326.32 159159
실시예 15Example 15 BH-2BH-2 화합물 15Compound 15 6.586.58 170170
실시예 16Example 16 BH-2BH-2 화합물 16Compound 16 6.606.60 162162
실시예 17Example 17 BH-1BH-1 화합물 17Compound 17 6.636.63 165165
비교예 1Comparative Example 1 BH-1BH-1 BD-1BD-1 2.702.70 5656
비교예 2Comparative Example 2 BH-1BH-1 BD-2BD-2 5.405.40 136136
본 발명의 일 실시상태에 따른 화합물 1 내지 17은 나프탈렌에 하나의 시클로헥산 고리가 축합된 다환 고리에 벤조퓨란이 축합된 코어 구조를 가지면서 2개의 아릴아민기를 갖는다. 반면, 비교예 1의 화합물 BD-1은 하나의 아릴아민기만을 갖거나, 비교예 2의 화합물 BD-2는 나프탈렌에 2개의 시클로헥산 고리가 축합된 코어 구조를 갖는다.Compounds 1 to 17 according to an exemplary embodiment of the present invention have two arylamine groups while having a core structure in which a benzofuran is condensed in a polycyclic ring in which one cyclohexane ring is condensed in naphthalene. On the other hand, Compound BD-1 of Comparative Example 1 has only one arylamine group, or Compound BD-2 of Comparative Example 2 has a core structure in which two cyclohexane rings are condensed in naphthalene.
상기 표 1에서 보는 바와 같이, 화학식 1의 구조를 갖는 화합물을 사용한 실시예 1 내지 17의 소자는 비교예 1 및 2의 소자보다 청색 고효율 및 장수명의 특성을 가진다. As shown in Table 1, the devices of Examples 1 to 17 using the compound having the structure of Formula 1 have properties of blue high efficiency and long life compared to those of Comparative Examples 1 and 2.

Claims (11)

  1. 하기 화학식 1로 표시되는 화합물:Compound represented by the formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2019017713-appb-I000077
    Figure PCTKR2019017713-appb-I000077
    상기 화학식 1에 있어서,In Chemical Formula 1,
    R1 내지 R8는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트로기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 치환기가 결합하여 치환 또는 비치환된 고리를 형성하고,R1 to R8 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitro group; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, or adjacent substituents combine to form a substituted or unsubstituted ring,
    Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    r7은 1 또는 2이고, 2인 경우 R7은 서로 동일하거나 상이하고,r7 is 1 or 2, when 2 R7 is the same or different from each other,
    r8은 1 내지 3의 정수이고, 2 이상인 경우 R8은 서로 동일하거나 상이하다.r8 is an integer of 1 to 3, and when 2 or more, R8 is the same or different from each other.
  2. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 1-1 내지 1-4 중 어느 하나로 표시되는 것인 화합물:The method according to claim 1, wherein Formula 1 is a compound represented by any one of the following Formulas 1-1 to 1-4:
    [화학식 1-1][Formula 1-1]
    Figure PCTKR2019017713-appb-I000078
    Figure PCTKR2019017713-appb-I000078
    [화학식 1-2][Formula 1-2]
    Figure PCTKR2019017713-appb-I000079
    Figure PCTKR2019017713-appb-I000079
    [화학식 1-3][Formula 1-3]
    Figure PCTKR2019017713-appb-I000080
    Figure PCTKR2019017713-appb-I000080
    [화학식 1-4][Formula 1-4]
    Figure PCTKR2019017713-appb-I000081
    Figure PCTKR2019017713-appb-I000081
    상기 화학식 1-1 내지 1-4에 있어서, In Chemical Formulas 1-1 to 1-4,
    R1 내지 R8, Ar1 내지 Ar4, r7 및 r8의 정의는 화학식 1에서 정의한 바와 같다.The definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
  3. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 2-1 내지 2-4 중 어느 하나로 표시되는 화합물:The method according to claim 1, wherein Formula 1 is a compound represented by any one of the following Formulas 2-1 to 2-4:
    [화학식 2-1][Formula 2-1]
    Figure PCTKR2019017713-appb-I000082
    Figure PCTKR2019017713-appb-I000082
    [화학식 2-2][Formula 2-2]
    Figure PCTKR2019017713-appb-I000083
    Figure PCTKR2019017713-appb-I000083
    [화학식 2-3][Formula 2-3]
    Figure PCTKR2019017713-appb-I000084
    Figure PCTKR2019017713-appb-I000084
    [화학식 2-4][Formula 2-4]
    Figure PCTKR2019017713-appb-I000085
    Figure PCTKR2019017713-appb-I000085
    상기 화학식 2-1 내지 2-4에 있어서,In Chemical Formulas 2-1 to 2-4,
    R1 내지 R8, Ar1 내지 Ar4, r7 및 r8의 정의는 화학식 1에서 정의한 바와 같다.The definitions of R1 to R8, Ar1 to Ar4, r7 and r8 are as defined in Formula 1.
  4. 청구항 1에 있어서,The method according to claim 1,
    Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 할로겐기, 니트릴기, C1-C5의 알킬기, C3-C10의 시클로알킬기, C6-C20의 아릴기 및 실릴기로 이루어진 군에서 선택된 하나 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 C6-C20의 아릴기; 또는 중수소, C1-C5의 알킬기 및 C3-C10의 시클로알킬기로 이루어진 군에서 선택된 하나 이상의 치환기 또는 상기 군에서 선택된 2 이상의 기가 연결된 치환기로 치환 또는 비치환된 C2-C20의 헤테로아릴기인 것인 화합물.Ar1 to Ar4 are the same as or different from each other, and each independently selected from the group consisting of deuterium, halogen, nitrile, C1-C5 alkyl, C3-C10 cycloalkyl, C6-C20 aryl and silyl groups Or a C6-C20 aryl group, which is unsubstituted or substituted with a substituent group of two or more groups selected from the group; Or a C2-C20 heteroaryl group unsubstituted or substituted with one or more substituents selected from the group consisting of deuterium, a C1-C5 alkyl group, and a C3-C10 cycloalkyl group, or two or more groups selected from the group.
  5. 청구항 1에 있어서, The method according to claim 1,
    R1 내지 R6는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 중수소로 치환 또는 비치환된 C1-C5의 알킬기; 또는 C6-C30의 아릴기이거나, 인접한 치환기가 결합하여 플루오렌 고리를 형성하는 것인 화합물.R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A C1-C5 alkyl group unsubstituted or substituted with deuterium; Or a C6-C30 aryl group, or adjacent substituents combine to form a fluorene ring.
  6. 청구항 1에 있어서, R7 및 R8은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 또는 중수소인 것인 화합물.The method according to claim 1, R7 and R8 are the same as or different from each other, and each independently hydrogen; Or deuterium.
  7. 청구항 1에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화합물 중에서 선택되는 어느 하나인 것인 화합물:The compound according to claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds:
    Figure PCTKR2019017713-appb-I000086
    Figure PCTKR2019017713-appb-I000086
    Figure PCTKR2019017713-appb-I000087
    Figure PCTKR2019017713-appb-I000087
    Figure PCTKR2019017713-appb-I000088
    Figure PCTKR2019017713-appb-I000088
    Figure PCTKR2019017713-appb-I000089
    Figure PCTKR2019017713-appb-I000089
    Figure PCTKR2019017713-appb-I000090
    Figure PCTKR2019017713-appb-I000090
    Figure PCTKR2019017713-appb-I000091
    Figure PCTKR2019017713-appb-I000091
    Figure PCTKR2019017713-appb-I000092
    Figure PCTKR2019017713-appb-I000092
    Figure PCTKR2019017713-appb-I000093
    Figure PCTKR2019017713-appb-I000093
    Figure PCTKR2019017713-appb-I000094
    .
    Figure PCTKR2019017713-appb-I000094
    .
  8. 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 청구항 1 내지 7 중 어느 한 항에 따른 화합물을 포함하는 것인 유기 발광 소자.A first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises the compound according to any one of claims 1 to 7. Light emitting element.
  9. 청구항 8에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물을 포함하는 것인 유기 발광 소자. The method according to claim 8, The organic layer comprises a light emitting layer, the light emitting layer is an organic light emitting device comprising the compound.
  10. 청구항 8에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화합물 및 하기 화학식 H로 표시되는 화합물을 포함하는 것인 유기 발광 소자:The method according to claim 8, The organic layer includes a light emitting layer, the light emitting layer is an organic light emitting device comprising the compound and the compound represented by the formula H:
    [화학식 H][Formula H]
    Figure PCTKR2019017713-appb-I000095
    Figure PCTKR2019017713-appb-I000095
    상기 화학식 H에 있어서,In the formula H,
    L21 및 L22는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L21 and L22 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    R21 내지 R28은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고,R21 to R28 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted phosphine oxide group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    Ar21 및 Ar22는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Ar21 and Ar22 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  11. 청구항 8에 있어서, 상기 유기물층은 발광층, 정공 주입층, 정공수송층, 전자 주입층, 전자 수송층, 전자 차단층 및 정공 차단층으로 이루어진 군에서 선택되는 1층 또는 2층 이상을 포함하는 것인 유기 발광 소자. The method according to claim 8, wherein the organic layer is a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, an electron blocking layer and a hole blocking layer selected from the group consisting of organic light emitting one or more layers device.
PCT/KR2019/017713 2018-12-14 2019-12-13 Compound and organic light-emitting device comprising same WO2020122671A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201980016113.1A CN111788198B (en) 2018-12-14 2019-12-13 Compound and organic light emitting device comprising the same

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2018-0161668 2018-12-14
KR20180161668 2018-12-14

Publications (1)

Publication Number Publication Date
WO2020122671A1 true WO2020122671A1 (en) 2020-06-18

Family

ID=71075538

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2019/017713 WO2020122671A1 (en) 2018-12-14 2019-12-13 Compound and organic light-emitting device comprising same

Country Status (3)

Country Link
KR (1) KR102428976B1 (en)
CN (1) CN111788198B (en)
WO (1) WO2020122671A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023063701A1 (en) * 2021-10-13 2023-04-20 주식회사 동진쎄미켐 Novel compound for capping layer, and organic light-emitting device comprising same

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112778319A (en) * 2021-01-20 2021-05-11 陕西莱特迈思光电材料有限公司 Organic compound, electronic element containing organic compound and electronic device
CN113501812B (en) * 2021-08-12 2022-10-14 长春海谱润斯科技股份有限公司 Triarylamine compound and organic electroluminescent device thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130119359A1 (en) * 2011-11-16 2013-05-16 Udc Ireland Limited Organic Electroluminescent Element, Material for Organic Electroluminescent Element, and Light Emitting Device, Display Device and Illumination Device Each Using the Element
US20140299851A1 (en) * 2011-04-12 2014-10-09 Udc Ireland Limited Organic Electroluminescence Element
KR20140134098A (en) * 2013-05-13 2014-11-21 덕산하이메탈(주) Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
KR20160121946A (en) * 2015-04-13 2016-10-21 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element comprising the same and electronic device thereof
KR20180018404A (en) * 2016-08-09 2018-02-21 주식회사 엘지화학 Heterocyclic compound and organic light emitting device comprising the same

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10135513B4 (en) 2001-07-20 2005-02-24 Novaled Gmbh Light-emitting component with organic layers
JP5973705B2 (en) * 2011-06-16 2016-08-23 ユー・ディー・シー アイルランド リミテッド Organic electroluminescent device, luminescent material for organic electroluminescent device, and light emitting device, display device and lighting device using the device
JP6063114B2 (en) * 2011-08-18 2017-01-18 ユー・ディー・シー アイルランド リミテッド ORGANIC ELECTROLUMINESCENT ELEMENT, ELEMENT MATERIAL, AND LIGHT EMITTING DEVICE, DISPLAY DEVICE AND LIGHTING DEVICE USING THE ELEMENT
JP6347909B2 (en) * 2011-08-22 2018-06-27 ユー・ディー・シー アイルランド リミテッド ORGANIC ELECTROLUMINESCENT ELEMENT, ELEMENT MATERIAL, AND LIGHT EMITTING DEVICE, DISPLAY DEVICE AND LIGHTING DEVICE USING THE ELEMENT
JP2013093541A (en) * 2011-10-06 2013-05-16 Udc Ireland Ltd Organic electroluminescent element and compound and material for organic electroluminescent element usable therefor, and luminescent device, display device and lighting device using the element
CN107089958A (en) * 2017-05-17 2017-08-25 中节能万润股份有限公司 A kind of pyrene class electroluminescent organic material, its preparation method and application

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20140299851A1 (en) * 2011-04-12 2014-10-09 Udc Ireland Limited Organic Electroluminescence Element
US20130119359A1 (en) * 2011-11-16 2013-05-16 Udc Ireland Limited Organic Electroluminescent Element, Material for Organic Electroluminescent Element, and Light Emitting Device, Display Device and Illumination Device Each Using the Element
KR20140134098A (en) * 2013-05-13 2014-11-21 덕산하이메탈(주) Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
KR20160121946A (en) * 2015-04-13 2016-10-21 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element comprising the same and electronic device thereof
KR20180018404A (en) * 2016-08-09 2018-02-21 주식회사 엘지화학 Heterocyclic compound and organic light emitting device comprising the same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023063701A1 (en) * 2021-10-13 2023-04-20 주식회사 동진쎄미켐 Novel compound for capping layer, and organic light-emitting device comprising same

Also Published As

Publication number Publication date
KR20200074045A (en) 2020-06-24
CN111788198A (en) 2020-10-16
KR102428976B1 (en) 2022-08-04
CN111788198B (en) 2023-09-05

Similar Documents

Publication Publication Date Title
WO2017171420A1 (en) Compound and organic light emitting element using same
WO2019235873A1 (en) Organic light-emitting device
WO2019225938A1 (en) Compound and organic light emitting diode comprising same
WO2020091521A1 (en) Compound and organic light emitting device comprising same
WO2018182297A1 (en) Benzocarbazole-based compound and organic light-emitting device comprising same
WO2020159279A1 (en) Polycyclic compound and organic light-emitting element comprising same
WO2020085765A1 (en) Polycyclic compound and organic light-emitting element comprising same
WO2021010656A1 (en) Organic light emitting element
WO2021125813A1 (en) Compound and organic light-emitting device comprising same
WO2020122671A1 (en) Compound and organic light-emitting device comprising same
WO2020184834A1 (en) Heterocyclic compound and organic light emitting device comprising same
WO2022103049A1 (en) Anthracene-based compound, and organic light-emitting device comprising same
WO2017052221A1 (en) Novel compound and organic light-emitting element comprising same
WO2021150048A1 (en) Organic light-emitting device
WO2020149610A1 (en) Heterocyclic compound and organic light-emitting device comprising same
WO2018236182A1 (en) Compound and organic electroluminescent device comprising same
WO2022039518A1 (en) Novel compound and organic light-emitting device comprising same
WO2021241882A1 (en) Compound and organic light-emitting device comprising same
WO2021167222A1 (en) Heterocyclic compound and organic light-emitting device comprising same
WO2021125814A1 (en) Compound and organic light-emitting device comprising same
WO2021034156A1 (en) Novel compound and organic light emitting device using same
WO2021029709A1 (en) Organic light-emitting device
WO2020246835A9 (en) Novel compound and organic light-emitting device using same
WO2020246837A9 (en) Novel compound and organic light emitting device comprising same
WO2020153654A1 (en) Compound and organic light-emitting element comprising same

Legal Events

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

Ref document number: 19894803

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19894803

Country of ref document: EP

Kind code of ref document: A1