WO2014112728A1 - Composé à base de pyrazole et dispositif électroluminescent organique l'utilisant - Google Patents

Composé à base de pyrazole et dispositif électroluminescent organique l'utilisant Download PDF

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WO2014112728A1
WO2014112728A1 PCT/KR2013/012134 KR2013012134W WO2014112728A1 WO 2014112728 A1 WO2014112728 A1 WO 2014112728A1 KR 2013012134 W KR2013012134 W KR 2013012134W WO 2014112728 A1 WO2014112728 A1 WO 2014112728A1
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substituted
unsubstituted
monocyclic
polycyclic
compound
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김동준
김미진
하양수
음성진
이주동
이준아
박건유
이정현
안용훈
김용우
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희성소재(주)
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
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    • C09K2211/1011—Condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene

Definitions

  • the present invention relates to a novel pyrazole compound and an organic light emitting device comprising the same.
  • the electroluminescent device is a kind of self-luminous display device, and has an advantage of having a wide viewing angle, excellent contrast, and fast response speed.
  • the organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from two electrodes are combined in the organic thin film to form a pair, then disappear and emit light.
  • the organic thin film may be composed of a single layer or multiple layers as necessary.
  • the material of the organic thin film may have a light emitting function as necessary.
  • a compound which may itself constitute a light emitting layer may be used, or a compound which may serve as a host or a dopant of a host-dopant-based light emitting layer may be used.
  • a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.
  • the present invention provides a novel pyrazole compound and an organic light emitting device comprising the same.
  • the present invention provides a compound of formula 1a:
  • R 1 and R 2 are halogen; C 2 Through C 60 A straight or branched chain substituted or unsubstituted alkenyl; Substituted or unsubstituted alkynyl of C 2 to C 60 straight or branched chain; C 1 to C 60 straight or branched chain substituted or unsubstituted alkoxy; C 3 to C 60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; Phosphoryl substituted with C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl (P
  • R 1 and R 2 is hydrogen; R 1 and R 2 of the other is halogen; C 2 Through C 60 A straight or branched chain substituted or unsubstituted alkenyl; C 2 to C 60 straight or branched substituted or unsubstituted alkynyl; C 1 to C 60 straight or branched chain substituted or unsubstituted alkoxy; C 3 to C 60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C 10 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 1 to C 20 an alkyl, C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl, or C 2 to substituted with a monocyclic or polycyclic substituted or unsubstituted heteroaryl group of C 60 of, C 6 to C 60 mono
  • R 1 and R 2 is C 1 to C 60 straight or branched chain substituted or unsubstituted alkyl; The other of R 1 and R 2 is halogen; C 2 Through C 60 A straight or branched chain substituted or unsubstituted alkenyl; C 2 to C 60 straight or branched substituted or unsubstituted alkynyl; C 1 to C 60 straight or branched chain substituted or unsubstituted alkoxy; C 3 to C 60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; Phosphoryl substituted with C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroary
  • R 3 to R 8 are the same as or different from each other, and independently hydrogen; halogen; Amines; C 1 to C 60 straight or branched chain substituted or unsubstituted alkyl; C 2 Through C 60 A straight or branched chain substituted or unsubstituted alkenyl; C 2 to C 60 straight or branched substituted or unsubstituted alkynyl; C 1 to C 60 straight or branched chain substituted or unsubstituted alkoxy; C 3 to C 60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C 6 to C 60 of the monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; Phosphoryl substituted with C 6 to C 60 monocyclic or polycyclic substituted
  • the present invention provides an organic light emitting device comprising an anode, a cathode and at least one organic material layer provided between the anode and the cathode, at least one layer of the organic material layer comprises a compound of formula 1b. :
  • R 1 to R 2 are the same as or different from each other, and independently hydrogen; halogen; C 1 to C 60 straight or branched chain substituted or unsubstituted alkyl; C 2 Through C 60 A straight or branched chain substituted or unsubstituted alkenyl; C 2 to C 60 straight or branched substituted or unsubstituted alkynyl; C 1 to C 60 straight or branched chain substituted or unsubstituted alkoxy; C 6 to C 60 straight or branched chain substituted or unsubstituted aryloxy; C 3 to C 60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 2 to C 60 of monocyclic or polycyclic substituted or unsubstituted heteroaryl;
  • R 3 to R 8 are the same as or different from each other, and independently hydrogen; halogen; Amines; C 1 to C 60 straight or branched chain substituted or unsubstituted alkyl; C 2 Through C 60 A straight or branched chain substituted or unsubstituted alkenyl; C 2 to C 60 straight or branched substituted or unsubstituted alkynyl; C 1 to C 60 straight or branched chain substituted or unsubstituted alkoxy; C 6 to C 60 straight or branched chain substituted or unsubstituted aryloxy; C 3 to C 60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroary
  • the compound described in this specification can be used as an organic material layer material of an organic light emitting element.
  • the compound may serve as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material in the organic light emitting device.
  • the compound according to one embodiment of the present specification may be used as a light emitting layer material of an organic light emitting device. Specifically, the compound may be used alone as a light emitting material, or may be used as a host material or a dopant material of the light emitting layer.
  • the compound according to another exemplary embodiment of the present specification may be used as a material for a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting an organic light emitting device.
  • 1 to 3 illustrate the stacking order of electrodes and organic material layers of organic light emitting diodes according to exemplary embodiments of the present invention.
  • 16 and 17 show E ox values derived as a result of CV measurement of compound 510.
  • 29 shows a PL measurement graph for 424 nm of compound 501.
  • FIG. 31 shows a PL measurement graph for 355 nm of compound 502.
  • FIG. 33 shows a PL measurement graph for 355 nm of compound 503.
  • FIG. 35 shows a PL measurement graph for 347 nm of compound 504.
  • FIG. 36 shows the UV measurement graph of compound 507.
  • FIG. 37 shows a PL measurement graph for 354 nm of compound 507.
  • FIG. 39 shows a PL measurement graph for 355 nm of compound 508.
  • 40 shows a UV measurement graph of compound 510.
  • 41 shows a PL measurement graph for 335 nm of compound 510.
  • FIG. 42 shows a UV measurement graph of compound 511.
  • FIG. 43 shows a PL measurement graph for 355 nm of compound 511.
  • 45 shows the PL measurement graph for 348 nm of compound 520.
  • FIG. 47 shows a PL measurement graph for 265 nm of Compound 522.
  • FIG. 49 shows a PL measurement graph for 360 nm of compound 562.
  • FIG. 51 shows a PL measurement graph for 329 nm of Compound 611.
  • Compounds described herein may be represented by Formula 1a or 1b.
  • the compound according to the present invention can be used as an organic material layer material of the organic light emitting device according to the structural and physical properties of the core structure.
  • halogen includes F, Cl, Br and I.
  • alkyl includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents.
  • the carbon number of the alkyl may be 1 to 60, specifically 1 to 40, more specifically 1 to 20.
  • alkenyl includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • Alkenyl may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more specifically 2 to 20 carbon atoms.
  • alkynyl includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • Alkynyl may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more specifically 2 to 20 carbon atoms.
  • alkoxy includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents.
  • the alkoxy may have 1 to 60 carbon atoms, specifically 1 to 40 carbon atoms, more specifically 1 to 20 carbon atoms.
  • cycloalkyl includes monocyclic or polycyclic having 3 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic means a group in which cycloalkyl is directly connected or condensed with another ring group.
  • the other ring group may be cycloalkyl, but may also be other types of ring groups such as heterocycloalkyl, aryl, heteroaryl, and the like.
  • the cycloalkyl may have 3 to 60 carbon atoms, specifically 3 to 40 carbon atoms, more specifically 5 to 20 carbon atoms.
  • heterocycloalkyl includes S, O or N as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic means a group in which heterocycloalkyl is directly connected or condensed with another ring group.
  • the other ring group may be heterocycloalkyl, but may also be other types of ring groups such as cycloalkyl, aryl, heteroaryl, and the like.
  • the heterocycloalkyl may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more specifically 3 to 20 carbon atoms.
  • aryl includes monocyclic or polycyclic having 6 to 60 carbon atoms, and may be further substituted with other substituents.
  • polycyclic means a group in which aryl is directly connected or condensed with another ring group.
  • the other ring group may be aryl, but may also be other types of ring groups such as cycloalkyl, heterocycloalkyl, heteroaryl, and the like.
  • the aryl may have 6 to 60 carbon atoms, specifically 6 to 40 carbon atoms, more specifically 6 to 20 carbon atoms.
  • aryl examples include phenyl, biphenyl, triphenyl, naphthyl, anthryl, chrysenyl, phenanthrenyl, peryllenyl, fluoranthenyl, triphenylenyl, pyrenyl, tetrasenyl, pentacenyl, fluorenyl , Indenyl, acenaphthylenyl, and the like or a condensed ring thereof, but are not limited thereto.
  • the heteroaryl includes S, O or N as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic means a group in which heteroaryl is directly connected or condensed with another ring group.
  • the other ring group may be heteroaryl, but may also be other types of ring groups such as cycloalkyl, heterocycloalkyl, aryl, and the like.
  • the heteroaryl may have 2 to 60 carbon atoms, specifically 2 to 40 carbon atoms, more specifically 3 to 20 carbon atoms.
  • heteroaryl examples include pyridyl, pyrimidyl, pyridazinyl, pyrrolyl, furanyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, fura Janyl, oxadiazolyl, thiadiazolyl, dithiazolyl, tetrazolyl, pyridinyl, pyranyl, thiopyranyl, diazinyl, oxazinyl, thiazinyl, dioxyyl, triazinyl, tetrazinyl, quinolyl , Isoquinolyl, quinazolinyl, isoquinazolinyl, acridinyl, phenantridinyl, imidazopyridinyl, diazanaphthalenyl, triazadinene, in
  • cycloalkylene, heterocycloalkylene, arylene and heteroarylene may be applied to the description of the aforementioned cycloalkyl, heterocycloalkyl, aryl and heteroaryl, respectively, except that they are divalent groups.
  • the spiro group includes a spiro structure, and may have 15 to 60 carbon atoms.
  • the spiro group may include a structure in which a 2,3-dihydro-1H-indene group or a cyclohexane group is spiro bonded to a fluorene group.
  • the spiro group includes a group of the following structural formula.
  • alkylamine, arylamine and heteroarylamine mean amines having one or two alkyl, aryl and heteroaryl, respectively, described above.
  • substituted or unsubstituted is C 1 to C 60 linear or branched alkyl; C 2 Through C 60 Straight or branched alkenyl; C 2 to C 60 straight or branched alkynyl; C 3 to C 60 monocyclic or polycyclic cycloalkyl; C 2 to C 60 monocyclic or polycyclic heterocycloalkyl; C 6 Through C 60 Monocyclic or polycyclic aryl; C 2 Through C 60 Monocyclic or polycyclic heteroaryl; C 2 to C 60 monocyclic or polycyclic heterocycloalkyl; C 10 to C 60 spiro groups; And amines unsubstituted or substituted with C 1 to C 20 alkyl, C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl, or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • substituted or unsubstituted means halogen, cyano, C 1 to C 60 straight or branched alkyl, C 2 to C 60 straight or branched alkenyl, C 2 to C 60 Straight or branched alkynyl, C 1 to C 60 straight or branched haloalkyl, C 2 to C 60 straight or branched haloalkenyl, C 2 to C 60 straight or branched haloalky Nyl, C 1 to C 60 straight or branched alkoxy, C 2 to C 60 straight or branched alkenyloxy, C 2 to C 60 straight or branched alkynyloxy, C 3 to C 60 Monocyclic or polycyclic cycloalkyl, C 2 to C 60 monocyclic or polycyclic heterocycloalkyl, C 6 to C 60 monocyclic or polycyclic aryl, C 2 to C 60 monocyclic or polycyclic heteroaryl, C 2 to C 60 monocyclic or polycyclic hetero
  • R 1 and R 2 either a is hydrogen, the other of R 1 and R 2 are C 3 to monocyclic or polycyclic substituted or unsubstituted of C 60 Cycloalkyl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C 10 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 1 to C 20 an alkyl, C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl, or C 2 to substituted with a monocyclic or polycyclic substituted or unsubstituted heteroaryl group of C 60 of, C 6 to C 60 monocyclic or polycyclic aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; Phosphoryl substituted with C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted of
  • R 1 and R 2 when any one of R 1 and R 2 is hydrogen, and the other of R 1 and R 2 is aryl, this aryl is C 10 to C 60 monocyclic or polycyclic substituted or unsubstituted Aryl; Or C 6 to C 60 monocyclic or polycyclic substituted aryl.
  • the monocyclic or polycyclic substituted or unsubstituted aryl group of C 10 to C 60 can be a substituted or unsubstituted group, or a linking group-substituted aromatic ring at least two fused rings, optionally be substituted with another substituent group added.
  • the C 6 to C 60 monocyclic or polycyclic substituted aryl is C 1 to C 20 alkyl, C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl or C 2 to C 60 monocyclic or polycyclic C 6 to C 60 monocyclic or polycyclic aryl substituted with substituted or unsubstituted heteroaryl.
  • any one of R 1 and R 2 is a straight or branched chain substituted or unsubstituted alkyl of C 1 to C 60 , the remaining of R 1 and R 2 One is C 3 to C 60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; Phosphoryl substituted with C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl (P ⁇ O); And amines substituted with C 1 to C 20 alkyl, C 6 to C 60 monocycl
  • R 1 and R 2 are the same or different from each other, hydrogen; C 1 to C 60 straight or branched chain substituted or unsubstituted alkyl; C 3 to C 60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; Phosphoryl substituted with C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl (P ⁇ O); And amines substituted with C 1 to C 20 alkyl, C 6 to C 60 monocyclic or polycyclic substituted
  • R 1 and R 2 are the same as or different from each other, C 3 to C 60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; Phosphoryl substituted with C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl (P ⁇ O); And amines substituted with C 1 to C 20 alkyl, C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl or C 2 to C 60 monocyclic or polycyclic
  • one of R 1 and R 2 is hydrogen, the other one of R 1 and R 2 is monocyclic or polycyclic substituted or unsubstituted C 10 to C 60 Aryl; C 1 to C 20 an alkyl, C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl, or C 2 to substituted with a monocyclic or polycyclic substituted or unsubstituted heteroaryl group of C 60 of, C 6 to C 60 monocyclic or polycyclic aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or an amine substituted with C 1 to C 20 alkyl, C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl, or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • any one of R 1 and R 2 is a straight or branched chain substituted or unsubstituted alkyl of C 1 to C 60 , the remaining of R 1 and R 2 One is C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or an amine substituted with C 1 to C 20 alkyl, C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl, or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R 1 and R 2 are the same as or different from each other, and hydrogen; C 1 to C 60 straight or branched chain substituted or unsubstituted alkyl; C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or an amine substituted with C 1 to C 20 alkyl, C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl, or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R 1 and R 2 are the same as or different from each other, C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl; C 2 Through C 60 Monocyclic or polycyclic substituted or unsubstituted heteroaryl; Or an amine substituted with C 1 to C 20 alkyl, C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl, or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • one of R 1 and R 2 is hydrogen, the other of R 1 and R 2 is substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, Substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted Fluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzofuran group
  • any one of R 1 and R 2 is a straight or branched chain substituted or unsubstituted alkyl of C 1 to C 60 , the remaining of R 1 and R 2 One is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted Phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstit
  • R 1 and R 2 are the same as or different from each other, and hydrogen, C 1 to C 60 linear or branched substituted or unsubstituted alkyl, substituted or unsubstituted Phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted phenanthrenyl, substituted or Unsubstituted pyrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyridyl
  • R 1 and R 2 are the same as or different from each other, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or Unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted fluore Nyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyridyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted phenyl, substituted or unsubstituted bi
  • R 1 or R 2 when R 1 or R 2 is a substituted amine, the amine is C 1 to C 20 alkyl, C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl or C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • amines may be substituted with straight or branched chain alkyl such as methyl, ethyl, propyl, butyl.
  • the amine may be substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted triphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted acenaphthylenyl, substituted or unsubstituted anthra Cenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted pyrenyl, substituted or unsubstituted indenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted furanyl, substituted or unsubstituted thienyl, substituted or unsubstituted Pyridyl, substituted or unsubstituted benzoxazolyl, substituted or unsubstituted benzofuran group, substituted or unsubstituted benzothiophene group
  • R 1 or R 2 is N- phenyl-naphthyl-amines, diphenylamine, di-naphthyl carbonyl amine, N- phenyl-fluorenyl-amine, N- naphthyl-fluorenyl-amine, dividers Phenylamine, N-naphthyl-dibenzofuranyl-amine, N-naphthyl-dibenzothienyl-amine, N-phenyl-biphenyl-amine, N-carbazolyl-fluorenyl-amine, N-naph Tyl-anthracenyl-amine, N-naphthyl-anthrylphenyl-amine, N-phenyl-diphenyltriazinyl-amine, N-naphthyl-diphenyltriazinyl-amine, or N-biphenyl-diphenyltria Gen
  • the substituent is halogen, cyano, C 1 to C 60 straight or branched chain alkyl, C 2 to C 60 straight or branched chain egg.
  • additional substituents include phenyl, naphthyl, anthracenyl, carbazolyl, alkylamine, arylamine, arylphosphoryl, pyridyl, furanyl, thienyl, C 1 -C 20 alkyl, phenyl or unsubstituted Ring triginyl and the like.
  • one of R 1 and R 2 is hydrogen, and the other one of R 1 and R 2 is biphenyl, triphenyl, naphthyl, anthracenyl, acenaph Thienyl, phenanthrenyl, pyrenyl, indenyl, naphthyl substituted phenyl, anthracenyl substituted phenyl, carbazolyl substituted phenyl, phenyl substituted with dimethylamine, phenyl substituted with diphenylamine, phenyl and naphthyl substituted Phenyl substituted with amine, phenyl substituted with diphenylphosphoryl, phenyl substituted with pyridyl, phenyl substituted with furanyl, phenyl substituted with thienyl, naphthyl substituted with naphthyl, anthracenyl substituted with phenyl Fluorenyl
  • one of R 1 and R 2 is methyl, ethyl or propyl
  • the other one of R 1 and R 2 is phenyl, biphenyl, triphenyl, naphthyl , Anthracenyl, acenaphthylenyl, phenanthrenyl, pyrenyl, indenyl, naphthyl substituted phenyl, anthracenyl substituted phenyl, carbazolyl substituted phenyl, phenyl substituted with dimethylamine, phenyl substituted with diphenylamine, phenyl And phenyl substituted with amine substituted with naphthyl, phenyl substituted with diphenylphosphoryl, phenyl substituted with pyridyl, phenyl substituted with furanyl, phenyl substituted with thienyl, naphthyl substituted with naphthy
  • R 1 and R 2 are the same as or different from each other, hydrogen, methyl, ethyl, propyl, phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, ace Naphthylenyl, phenanthrenyl, pyrenyl, indenyl, naphthyl substituted phenyl, anthracenyl substituted phenyl, carbazolyl substituted phenyl, phenyl substituted with dimethylamine, substituted with phenyl, phenyl and naphthyl substituted with diphenylamine Substituted amine, phenyl substituted with diphenylphosphoryl, phenyl substituted with pyridyl, phenyl substituted with furanyl, phenyl substituted with thienyl, naphthyl substituted with naphthyl, anthra
  • R 1 and R 2 are the same as or different from each other, phenyl, biphenyl, triphenyl, naphthyl, anthracenyl, acenaphthylenyl, phenanthrenyl Pyrenyl, indenyl, naphthyl substituted phenyl, anthracenyl substituted phenyl, carbazolyl substituted phenyl, phenyl substituted with dimethylamine, phenyl substituted with diphenylamine, phenyl substituted with phenyl and amine substituted with naphthyl, Phenyl substituted with diphenylphosphoryl, phenyl substituted with pyridyl, phenyl substituted with furanyl, phenyl substituted with thienyl, naphthyl substituted with naphthyl, anthracenyl substituted with phenyl
  • R 3 is C 3 Through C 60 Monocyclic or polycyclic substituted or unsubstituted cycloalkyl, C 2 Through C 60 Monocyclic or polycyclic substitution or Unsubstituted heterocycloalkyl, C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl, and C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R 3 is C 3 Through C 10 Monocyclic or polycyclic substituted or unsubstituted cycloalkyl, C 6 Through C 14 Monocyclic or polycyclic substitution or It may be selected from the group consisting of unsubstituted aryl and C 3 to C 6 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R 3 is substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted thienyl , Substituted or unsubstituted furanyl, and substituted or unsubstituted cyclopropyl.
  • R 3 may be selected from the group consisting of phenyl, naphthyl, pyridyl, thienyl, furanyl and cyclopropyl.
  • R 6 and R 7 are the same as or different from each other, and independently hydrogen, halogen, C 1 to C 6 linear or branched substituted or unsubstituted Alkoxy, C 6 to C 60 monocyclic or polycyclic substituted or unsubstituted aryl, C 2 to C 60 monocyclic or polycyclic substituted or unsubstituted heteroaryl, and C 1 to C 20 alkyl or C 6 to C It is selected from the group consisting of 60 monocyclic or polycyclic substituted or unsubstituted amine.
  • R 6 and R 7 are the same as or different from each other, and independently hydrogen, F, substituted or unsubstituted methoxy, substituted or unsubstituted phenyl, substituted Or unsubstituted diphenylamine, substituted or unsubstituted dimethylamine, and substituted or unsubstituted furanyl.
  • R 6 is hydrogen
  • R 7 is selected from the group consisting of F, methoxy, phenyl, diphenylamine, dimethylamine, and furanyl.
  • R 7 is hydrogen
  • R 6 is selected from the group consisting of F, methoxy, phenyl, diphenylamine, dimethylamine, and furanyl.
  • R 6 and R 7 are the same as or different from each other, and independently a group consisting of F, methoxy, phenyl, diphenylamine, dimethylamine, and furanyl Is selected from.
  • R 6 and R 7 are hydrogen.
  • R 4 , R 5 and R 8 is hydrogen.
  • the compounds described above may be prepared based on the preparation examples described below.
  • the compound of Formula 1a or 1b may be prepared by the same method as in Scheme 1 or 2. If necessary, substituents can be added or excluded. In addition, based on techniques known in the art, it is possible to change the starting materials, reactants, reaction conditions and the like.
  • Formula 1a or 1b is represented by the following Formula 1c.
  • At least one of R2, R3, and R7 is -L-NR9R10,
  • R9 and R10 are the same as or different from each other, and each independently C3 to C60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C2 to C60 monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C6 to C60 monocyclic or polycyclic substituted or unsubstituted aryl; And it is selected from the group consisting of C2 to C60 monocyclic or polycyclic substituted or unsubstituted heteroaryl,
  • L is a direct bond; C3 to C60 monocyclic or polycyclic substituted or unsubstituted cycloalkylene; C2 to C60 monocyclic or polycyclic substituted or unsubstituted heterocycloalkylene; C6 to C60 monocyclic or polycyclic substituted or unsubstituted arylene; And it is selected from the group consisting of C2 to C60 monocyclic or polycyclic substituted or unsubstituted heteroarylene,
  • a group other than -L-NR9R10, R1, R4, R5, R6, and R8 among R2, R3, and R7, is the same as or different from each other, and each independently hydrogen; halogen; C1 to C60 straight or branched chain substituted or unsubstituted alkyl; C2 to C60 straight or branched chain substituted or unsubstituted alkenyl; C2 to C60 straight or branched chain substituted or unsubstituted alkynyl; C1 to C60 straight or branched chain substituted or unsubstituted alkoxy; C6 to C60 straight or branched chain substituted or unsubstituted aryloxy; C3 to C60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C2 to C60 monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C6 to C60 monocyclic or polycyclic substituted or unsubstituted
  • the compound of Formula 1c is characterized in that it has -L-NR9R10 at a specific position of the core structure, that is, at least one of R2, R3 and R7.
  • the compound of Formula 1c may be represented by the following Formula 11, 12 or 13.
  • R1 to R10 and L are the same as defined in Chemical Formula 1c.
  • the compound of Formula 1c may include two or more core structures.
  • Chemical Formula 1c may be represented by the following Chemical Formulas 21, 22, or 23.
  • n is an integer from 1 to 3
  • R4, R5 and R8 are the same as or different from each other, and each independently hydrogen; Or C1 to C60 straight or branched chain substituted or unsubstituted alkyl.
  • R4 is hydrogen.
  • R7 is hydrogen; halogen; C1 to C60 straight or branched chain substituted or unsubstituted alkyl; C2 to C60 straight or branched chain substituted or unsubstituted alkenyl; C1 to C60 straight or branched chain substituted or unsubstituted alkoxy; C3 to C60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C2 to C60 monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C6 to C60 monocyclic or polycyclic substituted or unsubstituted aryl; And C2 to C60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R7 is hydrogen; F; C1 to C20 straight or branched chain substituted or unsubstituted alkyl; C6 to C60 monocyclic or polycyclic substituted or unsubstituted aryl; And C2 to C60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R7 is hydrogen; F; And C1 to C20 straight or branched chain substituted or unsubstituted alkyl.
  • R7 is hydrogen or F.
  • R3 and R7 are the same as or different from each other, and each independently hydrogen; C1 to C60 straight or branched chain substituted or unsubstituted alkyl; C3 to C60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C2 to C60 monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C6 to C60 monocyclic or polycyclic substituted or unsubstituted aryl; And C2 to C60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R3 and R7 are the same as or different from each other, and each independently hydrogen; C3 to C60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C2 to C60 monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C6 to C60 monocyclic or polycyclic substituted or unsubstituted aryl; And C2 to C60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R3 and R7 are the same as or different from each other, and each independently hydrogen; C3 to C60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C6 to C60 monocyclic or polycyclic substituted or unsubstituted aryl; And C2 to C60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R7 is hydrogen or halogen
  • R3 is hydrogen, C3 to C60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl
  • C6 to C60 monocyclic or polycyclic substituted or unsubstituted aryl.
  • R7 is hydrogen or halogen
  • R3 is hydrogen, C3 cycloalkyl
  • phenyl is hydrogen, in the formula 11, 13, 21 and 23, R7 is hydrogen or halogen
  • R3 is hydrogen, C3 cycloalkyl; And phenyl.
  • R3 and R2 are the same as or different from each other, and each independently hydrogen; C1 to C60 straight or branched chain substituted or unsubstituted alkyl; C3 to C60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C2 to C60 monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C6 to C60 monocyclic or polycyclic substituted or unsubstituted aryl; And C2 to C60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R3 and R2 are the same as or different from each other, and each independently hydrogen; C3 to C60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C2 to C60 monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C6 to C60 monocyclic or polycyclic substituted or unsubstituted aryl; And C2 to C60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R3 and R2 are the same as or different from each other, and each independently hydrogen; C3 to C60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C6 to C60 monocyclic or polycyclic substituted or unsubstituted aryl; And C2 to C60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R3 and R2 are each independently hydrogen, C3 cycloalkyl; And phenyl.
  • R3 and R2 are phenyl.
  • R3 is C3 cycloalkyl and R2 is phenyl.
  • R1 is hydrogen; C1 to C60 straight or branched chain substituted or unsubstituted alkyl; C3 to C60 monocyclic or polycyclic substituted or unsubstituted cycloalkyl; C2 to C60 monocyclic or polycyclic substituted or unsubstituted heterocycloalkyl; C6 to C60 monocyclic or polycyclic substituted or unsubstituted aryl; And C2 to C60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • R1 is hydrogen; C1 to C60 straight or branched chain substituted or unsubstituted alkyl; And C6 to C60 monocyclic or polycyclic substituted or unsubstituted aryl.
  • R1 is hydrogen; C1 to C20 straight or branched chain substituted or unsubstituted alkyl; And C6 to C20 monocyclic or polycyclic substituted or unsubstituted aryl.
  • R1 is hydrogen, methyl, ethyl or phenyl.
  • L is a direct bond; C6 to C60 monocyclic or polycyclic substituted or unsubstituted arylene; And C2 to C60 monocyclic or polycyclic substituted or unsubstituted heteroarylene.
  • L is a direct bond; Or C6 to C60 monocyclic or polycyclic substituted or unsubstituted arylene.
  • L is a direct bond; Or phenylene.
  • L is phenylene
  • L is a direct bond.
  • R9 and R10 are the same as or different from each other, and each independently C6 to C60 monocyclic or polycyclic substituted or unsubstituted aryl; And C2 to C60 monocyclic or polycyclic substituted or unsubstituted heteroaryl.
  • the compound of Formula 1c may be selected from the following compounds.
  • the organic light emitting device comprises the compound of Formula 1b described above.
  • the organic light emitting device according to the present invention includes an anode, a cathode and at least one organic material layer provided between the anode and the cathode, one or more of the organic material layer comprises a compound of formula 1b.
  • FIG. 1 to 3 illustrate the stacking order of electrodes and organic material layers of organic light emitting diodes according to exemplary embodiments of the present invention.
  • these drawings are not intended to limit the scope of the present invention, the structure of the organic light emitting device known in the art can be applied to the present invention.
  • an organic light emitting device in which an anode 200, an organic material layer 300, and a cathode 400 are sequentially stacked on a substrate 100 is illustrated.
  • the present invention is not limited thereto, and as shown in FIG. 2, an organic light emitting device in which a cathode, an organic material layer, and an anode are sequentially stacked on a substrate may be implemented.
  • the organic light emitting diode according to FIG. 3 includes a hole injection layer 301, a hole transport layer 302, a light emitting layer 303, a hole blocking layer 304, an electron transport layer 305, and an electron injection layer 306.
  • a hole injection layer 301 a hole transport layer 302
  • a light emitting layer 303 a hole transport layer 302
  • a hole blocking layer 304 a hole blocking layer 304
  • an electron transport layer 305 an electron injection layer 306.
  • the scope of the present invention is not limited by such a laminated structure, and other layers except for the light emitting layer may be omitted, and other functional layers may be added as needed.
  • the organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that the compound of Formula 1b is included in at least one layer of the organic material layer.
  • the compound of Formula 1b may constitute one or more layers of the organic material layer of the organic light emitting device alone. However, if necessary, the organic material layer may be mixed with other materials.
  • the compound of Formula 1b may be used as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material in the organic light emitting device.
  • the compound of Formula 1b may be used as a material of the light emitting layer of the organic light emitting device. Specifically, the compound of Formula 1b may be used as a light emitting material of the light emitting layer. In addition, the compound of Formula 1b may be used as a host material or a dopant material of the light emitting layer. The compound of Formula 1b may be used alone or in combination of two or more thereof. In addition, the compound of Formula 1b may be used in admixture with other kinds of compounds.
  • the present invention can be used as the material of the hole injection and / or transport layer of the organic light emitting device.
  • the compound of Formula 1c may be used as a material for the hole injection and / or transport layer of the organic light emitting device.
  • anode material materials having a relatively large work function may be used, and a transparent conductive oxide, a metal, or a conductive polymer may be used.
  • the cathode material materials having a relatively low work function may be used, and a metal, a metal oxide, or a conductive polymer may be used.
  • hole injection material a well-known hole injection material may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or described in Advanced Material, 6, p.677 (1994).
  • Starburst type amine derivatives such as TCTA, m-MTDATA, m-MTDAPB, polyaniline / dodecylbenzenesulfonic acid (polyaniline / dodecylbenzenesulfonic acid) or PEDOT / PSS (Poly (3, 4-ethylenedioxythiophene) / Poly (4-styrenesulfonate): poly (3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate)), Pani / CSA (Polyaniline / Camphor sulfonic acid: polyaniline / camphorsulfonic acid) or PANI / PSS (Polyaniline / Poly (4-styrene-sulfonate): polyaniline / poly (4-styrenesulfonate)) and the like can be used.
  • Polyaniline / dodecylbenzenesulfonic acid polyaniline / dodec
  • pyrazoline derivatives arylamine derivatives, stilbene derivatives, triphenyldiamine derivatives, and the like may be used, and low molecular or polymer materials may be used.
  • Examples of the electron transport material include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthraquinomethane and derivatives thereof, and fluorenone Derivatives, diphenyl dicyanoethylene and derivatives thereof, diphenoquinone derivatives, metal complexes of 8-hydroxyquinoline and derivatives thereof, and the like can be used, as well as high molecular weight materials as well as high molecular materials.
  • LiF is representatively used in the art, but the present invention is not limited thereto.
  • a red, green or blue light emitting material may be used, and if necessary, two or more light emitting materials may be mixed.
  • a fluorescent material may be used as the light emitting material, it may be used as a phosphorescent material.
  • a material which combines holes and electrons injected from the anode and the cathode, respectively, to emit light may be used, but materials in which both the host material and the dopant material are involved in light emission may be used.
  • the compound according to the present invention is used as a phosphorescent host material
  • those known in the art may be used as the phosphorescent dopant material to be used together.
  • phosphorescent dopant materials represented by LL'MX, LL'L “M, LMXX ', L2MX, and L3M can be used, but the scope of the present invention is not limited to these examples.
  • L, L ', L ", X and X' are bidentate ligands different from each other, and M is a metal which forms an 8-sided complex.
  • M may be iridium, platinum, osmium or the like.
  • L is an anionic bidentate ligand coordinated to M by sp2 carbon and hetero atom, and X may function to trap electrons or holes.
  • Non-limiting examples of L include 2- (1-naphthyl) benzoxazole, (2-phenylbenzooxazole), (2-phenylbenzothiazole), (2-phenylbenzothiazole), (7,8 -Benzoquinoline), (thienylpyridin), phenylpyridine, benzothienylpyridin, 3-methoxy-2-phenylpyridine, thienylpyridin, tolylpyridine and the like.
  • Non-limiting examples of X include acetylacetonate (acac), hexafluoroacetylacetonate, salicylidene, picolinate, 8-hydroxyquinolinate, and the like.
  • the organic layer was dried over anhydrous MgSO 4 , the solvent was removed using a rotary evaporator, and purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain the title compound 1-3 (4.8g, 85%).
  • the organic layer was dried over anhydrous MgSO 4 , the solvent was removed using a rotary evaporator, and purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain 4.6 g (81%) of the title compound 1-4 .
  • the organic layer was dried over anhydrous MgSO 4 , the solvent was removed using a rotary evaporator, and purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain 4.4 g (69%) of the target compound 1-8 .
  • the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator, and then purified by column chromatography using dichloromethane and hexane as a developing solvent, to obtain 2.3 g (73%) of the title compound ( 316 ).
  • the transparent electrode ITO thin film obtained from the glass for OLED was subjected to ultrasonic cleaning using trichloroethylene, acetone, ethanol and distilled water in sequence, and then stored in isopropanol and used.
  • the ITO substrate is installed in the substrate folder of the vacuum deposition equipment, and the following 2-TNATA (4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenyl is placed in a cell in the vacuum deposition equipment. amine).
  • NPB N, N'-bis ( ⁇ -naphthyl) -N, N'-diphenyl-4,4'-diamine
  • the phosphorescent green light emitting material having the following structure was deposited on the light emitting layer.
  • CBP 4,4'-bis (carbazol-9-yl) biphenyl
  • Ir (ppy) 3 a green light emitting dopant material
  • Tris (2-phenylpyridine) iridium (III) was 10% vacuum deposited relative to the host material.
  • BCP 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline
  • Alq 3 Tris (8-hydroxy-quinolinato) aluminium
  • lithium fluoride LiF
  • Al cathode was deposited to a thickness of 1000 ⁇ to produce an OLED.
  • the driving voltage, efficiency, and lifespan of the OLED devices manufactured in Examples and Comparative Examples are 1000 cd / m 2, and the results when the efficiency is 50% are shown in Table 2 below.
  • the organic layer was dried over anhydrous MgSO 4 , and the solvent was removed using a rotary evaporator, and then purified by column chromatography using dichloromethane and hexane as a developing solvent, to obtain 13.3 g (73%) of the target compound 501-2 .
  • the organic layer was dried over anhydrous MgSO 4 , the solvent was removed using a rotary evaporator, and purified by column chromatography using dichloromethane and hexane as a developing solvent, to obtain 7g (60%) of the target compound 2-3 .
  • the organic layer was dried over anhydrous MgSO 4 and purified by column chromatography using dichloromethane and hexane, which were freed of solvent by rotary evaporator, as a developing solvent, to obtain 7 g (quant.) Of the target compound 504 .
  • the organic layer was dried over anhydrous MgSO 4 , the solvent was removed using a rotary evaporator, and purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain 4 g (70%) of the title compound 507 .
  • the organic layer was dried over anhydrous MgSO 4 , the solvent was removed using a rotary evaporator, and purified by column chromatography using dichloromethane and hexane as a developing solvent to obtain 13.1 g (85%) of the titled Compound 4-1 .
  • Test Example 2 CV, UV and PL Measurements of Compounds 501, 502, 503, 504, 507, 508, 510, 511, 520, 521, 562 and 611
  • Homo, lumo and bandgap of compound 501, 502, 503, 504, 507, 508, 510, 511, 520, 521, 562 and 611 were measured by a CV measuring device (manufacturer: princeton appied research, model name: Parstat2273) was measured by the following method, and the results are shown in Tables 5 to 16 below.
  • Electrolyte solution 3.3 g of tetrabutylammonium tetrafluoroborate was precisely weighed and placed in a 100 ml volumetric flask, and methylene chloride was added to make 100 ml.
  • Standard solution Approximately 1 mg of NPB was precisely weighed, placed in a 10 ml volumetric flask, and the electrolyte was added to make 10 ml.
  • Sample solution About 1 mg of the compound was accurately weighed and placed in a 10 ml volumetric flask, and the electrolyte solution was added to 10 ml before being used as a sample solution.
  • 16 and 17 show E ox values derived as a result of CV measurement of compound 510.
  • the y axis represents current (unit: A), and the x axis represents potential (unit: V).
  • Figure 28 shows a UV measurement graph of the compound 501.
  • FIG. 31 shows a PL measurement graph for 355 nm of compound 502.
  • FIG. 33 shows a PL measurement graph for 355 nm of compound 503.
  • FIG. 35 shows a PL measurement graph for 347 nm of compound 504.
  • FIG. 36 shows the UV measurement graph of compound 507.
  • FIG. 37 shows a PL measurement graph for 354 nm of compound 507.
  • FIG. 39 shows a PL measurement graph for 355 nm of compound 508.
  • 40 shows a UV measurement graph of compound 510.
  • 41 shows a PL measurement graph for 335 nm of compound 510.
  • FIG. 42 shows a UV measurement graph of compound 511.
  • FIG. 43 shows a PL measurement graph for 355 nm of compound 511.
  • 45 shows the PL measurement graph for 348 nm of compound 520.
  • FIG. 47 shows a PL measurement graph for 265 nm of Compound 522.
  • FIG. 49 shows a PL measurement graph for 360 nm of compound 562.
  • FIG. 51 shows a PL measurement graph for 329 nm of Compound 611.
  • the y-axis in Figs. 28 to 51 are intensity respectively, and the x-axis is wavelength (unit: nm).
  • the transparent electrode ITO thin film obtained from the glass for OLED was subjected to ultrasonic washing using trichloroethylene, acetone, ethanol and distilled water in sequence, and used after washing in isopropyl alcohol.
  • an ITO substrate is placed in the substrate folder of the vacuum deposition equipment, and evacuated until the vacuum degree in the vacuum deposition equipment reaches 10 -7 torr, and then the following 4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenyl amine (4,4 ', 4 "-tris (N, N- (2-naphthyl) -phenylamino) triphenyl amine: 2-TNATA) was vapor deposited on the ITO substrate. A hole injection layer having a thickness of 600 ⁇ m was deposited on the substrate.
  • a hole transport layer was deposited to a thickness of 250 mm 3 on the hole injection layer using the compounds shown in Table 17.
  • a light emitting layer was deposited thereon as follows.
  • the following host was used as the light emitting material in one cell in the vacuum deposition equipment, and the following dopant was put in the other cell.
  • the following tris (8-hydroxyquinoline) aluminum (III) (Alq3) was deposited to a thickness of 200 ⁇ as an electron transport layer.
  • lithium fluoride LiF
  • Al cathode was deposited to a thickness of 1200 ⁇ to produce an OLED.

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Abstract

La présente invention porte sur un nouveau composé à base de pyrazole et sur un dispositif électroluminescent organique l'utilisant.
PCT/KR2013/012134 2013-01-17 2013-12-24 Composé à base de pyrazole et dispositif électroluminescent organique l'utilisant WO2014112728A1 (fr)

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CN104628624A (zh) * 2015-02-12 2015-05-20 陕西莱特光电材料股份有限公司 咔唑基三芳胺空穴传输材料及其合成方法
JP2020535185A (ja) * 2017-09-29 2020-12-03 エルティー・マテリアルズ・カンパニー・リミテッドＬＴ Ｍａｔｅｒｉａｌｓ Ｃｏ．， Ｌｔｄ． ヘテロ環化合物およびこれを含む有機発光素子
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CN114761409A (zh) * 2019-12-02 2022-07-15 Lt素材株式会社 杂环化合物以及包括其的有机发光元件
JP2023504806A (ja) * 2019-12-02 2023-02-07 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物及びこれを含む有機発光素子
JP2023505034A (ja) * 2019-12-02 2023-02-08 エルティー・マテリアルズ・カンパニー・リミテッド ヘテロ環化合物及びこれを含む有機発光素子

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