WO2016175624A1 - Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé - Google Patents

Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé Download PDF

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WO2016175624A1
WO2016175624A1 PCT/KR2016/004567 KR2016004567W WO2016175624A1 WO 2016175624 A1 WO2016175624 A1 WO 2016175624A1 KR 2016004567 W KR2016004567 W KR 2016004567W WO 2016175624 A1 WO2016175624 A1 WO 2016175624A1
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group
substituted
unsubstituted
light emitting
formula
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라현주
정원장
이현주
이진우
최진석
최대혁
이주동
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희성소재(주)
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Priority to CN201680024859.3A priority Critical patent/CN107548399B/zh
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    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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]
    • H10K50/18—Carrier blocking layers

Definitions

  • the present application relates to a heterocyclic compound and an organic light emitting device using 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 element has a structure in which an organic thin film is arranged 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 needed.
  • a compound which may itself constitute a light emitting layer may be used, or a compound that 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 of hole injection, hole transport, electron blocking, hole blocking, electron transport, electron injection, or the like may be used.
  • R1 is hydrogen or deuterium, represented by-(L1) p- (Y1) q,
  • R2 is hydrogen, deuterium or naphthyl, or is represented by-(L2) r- (Y2) s,
  • L1 and L2 are each independently a substituted or unsubstituted arylene group; And a substituted or unsubstituted ring or polycyclic heteroarylene group,
  • r is 0 to 10
  • s is 1 to 10
  • R, R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; -CN; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or It is an unsubstituted heteroaryl group.
  • an organic light emitting device including an anode, a cathode, and one or more organic material layers provided between the anode and the cathode, wherein one or more layers of the organic material layers include the heterocyclic compound.
  • an element Provided is an element.
  • the heterocyclic compound according to the exemplary embodiment of the present application may be used as an organic material layer material of the organic light emitting device.
  • the heterocyclic compound may be used as a material such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer in the organic light emitting device.
  • the heterocyclic compound represented by Formula 1 may be used as a material of an electron transporting layer, a hole transporting layer or a light emitting layer of the organic light emitting device.
  • organic light emitting device represented by the formula (1) can reduce the drive voltage of the device, improve the light efficiency, and can improve the life characteristics of the device by the thermal stability of the compound.
  • 1 to 4 are diagrams schematically showing a laminated structure of an organic light emitting device according to an exemplary embodiment of the present application.
  • FIG. 5 shows a PL measurement graph at 286 nm wavelength of compound 16.
  • FIG. 6 shows a PL measurement graph at 328 nm wavelength of compound 16.
  • FIG. 7 shows a PL measurement graph at 404 nm wavelength of compound 16.
  • FIG. 12 shows a PL measurement graph at 280 nm wavelength of compound 44.
  • FIG. 13 shows a PL measurement graph at 414 nm wavelength of Compound 44.
  • Heterocyclic compound according to an exemplary embodiment of the present application is characterized in that represented by the formula (1). More specifically, the heterocyclic compound represented by Formula 1 may be used as an organic material layer material of the organic light emitting device by the structural features of the core structure and the substituents as described above.
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2 to 7.
  • R, R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; -CN; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted aryl group; or substituted or Unsubstituted heteroaryl group,
  • n are each independently an integer of 0 to 7, when m is 2 or more, two or more R11 are the same or different from each other,
  • n is each independently an integer of 0 to 5, and when n is 2 or more, two or more R 11 are the same or different from each other.
  • R1 when R2 of the formula (1) is hydrogen or deuterium, R1 may be represented by-(L1) p- (Y1) q.
  • L1 of Chemical Formula 1 is a substituted or unsubstituted arylene group
  • R2 in the case where R1 of Formula 1 is hydrogen or deuterium, R2 may be represented by a naphthyl group or-(L2) r- (Y2) s. R2 may be an unsubstituted naphthyl group.
  • L2 of the general formula (1) is a substituted or unsubstituted arylene group
  • Y2 is a substituted or unsubstituted aryl group
  • And -P ( 0) RR '.
  • p and r of Formula 1 may be each independently 0 to 10, may be 1 to 10.
  • R3 to R10 of Chemical Formula 1 may be each independently hydrogen or deuterium.
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group and can be interpreted as a substituent to which two phenyl groups are linked. Said additional substituents may be further substituted further.
  • R, R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; -CN; substituted or unsubstituted C 1 to C 60 straight or branched alkyl group; substituted or unsubstituted C 3 To C 60 monocyclic or polycyclic cycloalkyl group, substituted or unsubstituted C 6 to C 60 monocyclic or polycyclic aryl group, or substituted or unsubstituted C 2 to C 60 monocyclic or polycyclic heteroaryl group.
  • R, R 'and R are the same as or different from each other, and each independently hydrogen; deuterium; -CN; deuterium, halogen, -CN, C 1 to C 20 alkyl group, C 6 to C 60 aryl group, and C 2 to C 60 substituted heteroaryl or unsubstituted alkyl group of C 1 to C 60; an aryl group of deuterium, halogen, -CN, C 1 to C 20 alkyl group, C 6 to C 60 a, and C 2 A C 3 to C 60 cycloalkyl group unsubstituted or substituted with a C 6 to C 60 heteroaryl group; deuterium, halogen, —CN, an alkyl group of C 1 to C 20 , an aryl group of C 6 to C 60 , and C 2 to C 60 substituted or unsubstituted group heteroaryl C 6 to C 60 aryl group; or an alkyl group of deuterium, halogen, -CN, C 1 to
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
  • the halogen may be fluorine, chlorine, bromine or iodine.
  • the alkyl group includes a straight or branched chain having 1 to 60 carbon atoms, and may be further substituted by other substituents. Carbon number of the alkyl group may be 1 to 60, specifically 1 to 40, more specifically, 1 to 20.
  • Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl
  • the alkenyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent. Carbon number of the alkenyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.
  • Specific examples thereof include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, and 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(Naphthyl-1-yl) vinyl-1-yl group, 2,2-bis (diphenyl-1-yl) vinyl-1-yl group, stilbenyl group, styrenyl group and the like, but are not limited thereto.
  • the alkynyl group includes a straight or branched chain having 2 to 60 carbon atoms, and may be further substituted by another substituent.
  • Carbon number of the alkynyl group may be 2 to 60, specifically 2 to 40, more specifically, 2 to 20.
  • the cycloalkyl group includes a monocyclic or polycyclic ring having 3 to 60 carbon atoms, and may be further substituted by other substituents.
  • polycyclic means a group in which a cycloalkyl group is directly connected or condensed with another ring group.
  • the other ring group may be a cycloalkyl group, but may be another type of ring group, such as a heterocycloalkyl group, an aryl group, a heteroaryl group, or the like.
  • Carbon number of the cycloalkyl group may be 3 to 60, specifically 3 to 40, more specifically 5 to 20.
  • the heterocycloalkyl group includes O, S, Se, N, or Si 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 a heterocycloalkyl group is directly connected or condensed with another ring group.
  • the other ring group may be a heterocycloalkyl group, but may be another type of ring group, such as a cycloalkyl group, an aryl group, a heteroaryl group, or the like.
  • Carbon number of the heterocycloalkyl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 20.
  • the aryl group includes a monocyclic or polycyclic ring having 6 to 60 carbon atoms, and may be further substituted by another substituent.
  • the polycyclic means a group in which an aryl group is directly connected or condensed with another ring group.
  • the other ring group may be an aryl group, but may be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, a heteroaryl group, or the like.
  • the aryl group includes a spiro group. Carbon number of the aryl group may be 6 to 60, specifically 6 to 40, more specifically 6 to 25.
  • aryl group examples include phenyl group, biphenyl group, triphenyl group, naphthyl group, anthryl group, chrysenyl group, phenanthrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, phenenyl group, pyre Neyl group, tetrasenyl group, pentaxenyl group, fluorenyl group, indenyl group, acenaphthylenyl group, benzofluorenyl group, spirobifluorenyl group, 2,3-dihydro-1H-indenyl group, condensed ring groups thereof Etc., but is not limited thereto.
  • the spiro group is a group including 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 fluorenyl group.
  • the following spiro groups may include any of the groups of the following structural formula.
  • the heteroaryl group includes S, O, Se, N, or Si as a hetero atom, includes a monocyclic or polycyclic ring having 2 to 60 carbon atoms, and may be further substituted by another substituent.
  • the polycyclic means a group in which a heteroaryl group is directly connected or condensed with another ring group.
  • the other ring group may be a heteroaryl group, but may be another type of ring group, such as a cycloalkyl group, a heterocycloalkyl group, an aryl group, or the like.
  • Carbon number of the heteroaryl group may be 2 to 60, specifically 2 to 40, more specifically 3 to 25.
  • heteroaryl group examples include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophene, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl and thiazolyl Group, isothiazolyl group, triazolyl group, furazanyl group, oxdiazolyl group, thiadiazolyl group, dithiazolyl group, tetrazolyl group, pyranyl group, thiopyranyl group, diazinyl group, oxazinyl group , Thiazinyl group, dioxyyl group, triazinyl group, tetragenyl group, quinolyl group, isoquinolyl group, quinazolinyl group, isoquinazolinyl group, quinozolyl group, naphthyridyl group, acridinyl group, phenan
  • the amine group is a monoalkylamine group; Monoarylamine group; Monoheteroarylamine group; -NH 2 ; Dialkylamine groups; Diarylamine group; Diheteroarylamine group; Alkylarylamine group; Alkyl heteroaryl amine group; And it may be selected from the group consisting of arylheteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, dibiphenylamine group, anthracenylamine group, 9- Methyl-anthracenylamine group, diphenylamine group, phenylnaphthylamine group, ditolylamine group, phenyltolylamine group, triphenylamine group, biphenylnaphthylamine group, phenylbiphenylamine group, biphenylfluore And a phenylamine group, a phenyltriphenylenylamine group, a biphenyltriphenylenylamine group, and the like, but are not limited thereto.
  • an arylene group means one having two bonding positions, that is, a divalent group.
  • the description of the aforementioned aryl group can be applied except that they are each divalent.
  • a heteroarylene group means a thing which has two bonding positions, ie, a bivalent group, in a heteroaryl group.
  • the description of the aforementioned heteroaryl group can be applied except that they are each divalent.
  • Y1 or Y2 of Formula 1 is X3 and X4 are substituted or unsubstituted aromatic hydrocarbon rings; Or a substituted or unsubstituted aromatic hetero ring.
  • Z One To Z 3 are the same as or different from each other, each independently S or O,
  • Z 4 to Z 9 are the same as or different from each other, and are each independently CR ′ R ′′, NR ′, S or O,
  • R 'and R are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.
  • Formula 1 may be represented by any one of the compounds of the following [Group 1], but is not limited thereto.
  • Chemical Formula 1 may be represented by any one of the following Group 2 compounds, but is not limited thereto.
  • the heterocyclic compound has a high glass transition temperature (Tg) is excellent in thermal stability. This increase in thermal stability is an important factor in providing drive stability to the device.
  • the heterocyclic compound according to one embodiment of the present application may be prepared by a multistage chemical reaction. Some intermediate compounds may be prepared first, and compounds of formula 1 may be prepared from the intermediate compounds. More specifically, the heterocyclic compound according to one embodiment of the present application may be prepared based on the preparation examples described below.
  • Another embodiment of the present application provides an organic light emitting device including the heterocyclic compound represented by Formula 1.
  • the organic light emitting device may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic material layers are formed using the heterocyclic compound described above.
  • the heterocyclic compound may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, roll coating and the like, but is not limited thereto.
  • the organic light emitting device 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 is a hetero ring represented by the formula (1) Compound.
  • FIG. 1 to 3 illustrate a lamination order of an electrode and an organic material layer of an organic light emitting diode according to an exemplary embodiment of the present application.
  • these drawings are not intended to limit the scope of the present application, the structure of the organic light emitting device known in the art can be applied to the present application.
  • 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 illustrated 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 device 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 application 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 includes an anode, a cathode, and two or more stacks provided between the anode and the cathode, each of the two or more stacks each independently includes a light emitting layer, and the two or more stacks.
  • the charge generating layer comprises a heterocyclic compound represented by the formula (1).
  • an organic light emitting diode includes an anode, a first stack provided on the anode and including a first emission layer, a charge generation layer provided on the first stack, and the charge generation layer. And a second stack provided on the second stack including the second light emitting layer, and a cathode provided on the second stack.
  • the charge generating layer may include a heterocyclic compound represented by the formula (1).
  • each of the first stack and the second stack may independently include at least one of the above-described hole injection layer, hole transport layer, hole blocking layer, electron transport layer, electron injection layer, and the like.
  • the charge generating layer may be an N-type charge generating layer, and the charge generating layer may further include a dopant known in the art in addition to the heterocyclic compound represented by Formula 1.
  • an organic light emitting device having a 2-stack tandem structure is schematically illustrated in FIG. 4.
  • the first electronic blocking layer, the first hole blocking layer, the second hole blocking layer and the like described in FIG. 4 may be omitted in some cases.
  • the organic light emitting device according to the present specification may be manufactured by materials and methods known in the art, except for including the heterocyclic compound represented by Chemical Formula 1 in at least one layer of the organic material layer.
  • the heterocyclic compound represented by Chemical Formula 1 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 heterocyclic compound represented by Chemical Formula 1 may be used as an electron transport layer, a hole blocking layer, a light emitting layer, or the like in an organic light emitting device.
  • the heterocyclic compound represented by Formula 1 may be used as a material of an electron transporting layer, a hole transporting layer, or a light emitting layer of an organic light emitting device.
  • the heterocyclic compound represented by Formula 1 may be used as a material of the light emitting layer in the organic light emitting device.
  • the heterocyclic compound represented by Formula 1 may be used as a material of the phosphorescent host of the light emitting layer in the organic light emitting device.
  • the 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 positive electrode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); A combination of a metal and an oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methyl compound), poly [3,4- (ethylene-1,2-dioxy) compound] (PEDT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • 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.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • a well-known hole injection material may be used, for example, phthalocyanine compounds such as copper phthalocyanine disclosed in US Pat. No. 4,356,429 or described in Advanced Material, 6, p.677 (1994).
  • Starburst amine derivatives such as tris (4-carbazoyl-9-ylphenyl) amine (TCTA), 4,4 ', 4 "-tri [phenyl (m-tolyl) amino] triphenylamine (m- MTDATA), 1,3,5-tris [4- (3-methylphenylphenylamino) phenyl] benzene (m-MTDAPB), polyaniline / dodecylbenzenesulfonic acid, or poly (line) 3,4-ethylenedioxythiophene) / poly (4-styrenesulfonate) (Poly (3,4-ethylenedioxythiophene) / Poly (4-styrenesulfonate)), polyaniline / Cam
  • 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 transporting material include oxadiazole derivatives, anthraquinodimethane and derivatives thereof, benzoquinone and derivatives thereof, naphthoquinone and derivatives thereof, anthraquinone and derivatives thereof, tetracyanoanthhraquinomethane 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 application 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 can be used as a light emitting material, it can also 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 organic light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type according to a material used.
  • the heterocyclic compound according to the exemplary embodiment of the present application may act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like.
  • B-1 (1 eq.), Iodobenzene, 1.5 eq., Cu (0.05 eq.), 18-crown-6-ether (18-Crown) O-DCB (20 ml) mixture of -6-ether, 0.05 eq.), K 2 CO 3 (2 eq.) was refluxed for 16 hours.
  • FIG. 5 shows a PL measurement graph at 286 nm wavelength of compound 16.
  • FIG. 6 shows a PL measurement graph at 328 nm wavelength of compound 16.
  • FIG. 7 shows a PL measurement graph at 404 nm wavelength of compound 16.
  • FIG. 12 shows a PL measurement graph at 280 nm wavelength of compound 44.
  • FIG. 13 shows a PL measurement graph at 414 nm wavelength of Compound 44.
  • the glass substrate coated with the thin film of ITO to a thickness of 1500 kPa was washed by distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as acetone, methanol, isopropyl alcohol and the like was dried and then treated with UVO for 5 minutes using UV in a UV cleaner. Subsequently, the substrate was transferred to a plasma cleaner (PT), and then plasma-treated to remove ITO work function and residual film in a vacuum state, and then transferred to a thermal deposition apparatus for organic deposition.
  • PT plasma cleaner
  • An organic material was formed on the ITO transparent electrode (anode) in a 2 stack WOLED (White Orgainc Light Device) structure.
  • the first stack was first vacuum-deposited TAPC to a thickness of 300 kPa to form a hole transport layer. After the hole transport layer was formed, the light emitting layer was thermally vacuum deposited on it as follows. The light emitting layer was deposited to 300 ⁇ by dope 8% of FIrpic with blue phosphor dopant on the host TCz1.
  • the electron transporting layer was formed using 400mW using TmPyPB, and then, 100% by Cs 2 CO 3 doped to 20% of the compound shown in Table 7 as a charge generating layer.
  • MoO 3 was thermally vacuum deposited to a thickness of 50 kPa to form a hole injection layer.
  • Common layer is then in the hole transport layer is doped with the MoO 3 20% in TAPC 100 ⁇ formed, the TAPC was formed by depositing 300 ⁇ , the over light-emitting layer and the green phosphorescent topeon open Ir (ppy) 3 in the host TCz1 doped with 8%
  • 600 mW was formed using TmPyPB as the electron transport layer.
  • lithium fluoride (LiF) is deposited on the electron transport layer to form a electron injecting layer by depositing 10 ⁇ thick.
  • an aluminum (Al) cathode is deposited to a thickness of 1,200 ⁇ on the electron injecting layer to form a cathode.
  • a light emitting device was manufactured.
  • the electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured by Maxiers M7000, and the reference luminance was 3,500 cd / m using the life measurement equipment (M6000) manufactured by McScience Inc. with the measurement result. When m 2 , T 95 was measured.
  • the driving voltage, the luminous efficiency, the external quantum efficiency, and the color coordinates (CIE) of the white organic light emitting diodes manufactured according to the present invention were measured as shown in Table 9.
  • the organic light emitting device using the charge generating layer material of the two-stack white organic light emitting device of the present invention has a lower driving voltage and improved luminous efficiency than Comparative Example 1.
  • the compound of the present invention used as an N-type charge generating layer composed of an invented backbone having appropriate length, strength and flat properties and a suitable heterocompound capable of binding to a metal is selected from alkali or alkaline earth metals. It is assumed that a gap state is formed in the N-type charge generation layer, and electrons generated from the P-type charge generation layer may be easily injected into the electron transport layer through the gap state generated in the N-type charge generation layer. Judging. Therefore, the P-type charge generating layer can perform electron injection and electron transfer well to the N-type charge generating layer. Therefore, the driving voltage of the organic light emitting device is lowered, and the efficiency and lifetime are considered to be improved.
  • the transparent electrode ITO thin film obtained from the glass for OLED was subjected to ultrasonic cleaning for 5 minutes using trichloroethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol and used.
  • N, N'-bis ( ⁇ -naphthyl) -N, N'-diphenyl-4,4'-diamine (N, N'-bis ( ⁇ -naphthyl) -N, N'-diphenyl-4,4'-diamine: NPB) was added thereto, and a 300 ⁇ thick hole transport layer was deposited on the hole injection layer by evaporation by applying a current to the cell.
  • a blue light emitting material having the following structure was deposited as a light emitting layer thereon. Specifically, H1, a blue light emitting host material, was vacuum deposited to a thickness of 200 ⁇ in one cell in the vacuum deposition equipment, and D1, a blue light emitting dopant material, was vacuum deposited on the cell at 5% of the host material.
  • Lithium fluoride (LiF) was deposited to an electron injecting layer with a thickness of 10 mW and an OLED was fabricated with an Al cathode having a thickness of 1000 mW.
  • the electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured with M7000's M7000, and the reference luminance was 700 cd through the life measurement equipment (M6000) manufactured by McScience Inc. with the measurement results. T 95 was measured at / m 2 .
  • the driving voltage, the luminous efficiency, the external quantum efficiency, and the color coordinate (CIE) of the organic electroluminescent device manufactured according to the present invention were measured as shown in Table 10.
  • the organic light emitting device using the electron transporting layer material of the blue organic light emitting device of the present invention has a lower driving voltage and significantly improved luminous efficiency and lifespan compared to Comparative Example 2.
  • the compound of the present invention has improved in terms of driving, efficiency, and lifespan by improving the improved electron-transporting property or improved stability.
  • the glass substrate coated with the thin film of ITO to a thickness of 1500 kPa was washed by distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as acetone, methanol, isopropyl alcohol and the like was dried and then treated with UVO for 5 minutes using UV in a UV cleaner. Subsequently, the substrate was transferred to a plasma cleaner (PT), and then plasma-treated to remove ITO work function and residual film in a vacuum state, and then transferred to a thermal deposition apparatus for organic deposition.
  • PT plasma cleaner
  • An organic material was formed on the ITO transparent electrode (anode) in a 2 stack WOLED (White Orgainc Light Device) structure.
  • the first stack was first vacuum-deposited TAPC to a thickness of 300 kPa to form a hole transport layer. After the hole transport layer was formed, the light emitting layer was thermally vacuum deposited on it as follows. The light emitting layer was deposited at 300 ⁇ by dope 8% of FIrpic with blue phosphorescent dopant on TCz1.
  • the electron transporting layer was formed using 400mW using TmPyPB, and then, 100% of the charge generating layer was formed by doping 20% of Cs 2 CO 3 to the compound shown in Table 5 below.
  • MoO 3 was thermally vacuum deposited to a thickness of 50 kPa to form a hole injection layer.
  • Common layer is then in the hole transport layer is doped with the MoO 3 20% in TAPC 100 ⁇ formed, the TAPC was formed by depositing 300 ⁇ , the over light-emitting layer and the green phosphorescent topeon open Ir (ppy) 3 in the host TCz1 doped with 8%
  • 600 mW was formed using TmPyPB as the electron transport layer.
  • lithium fluoride (LiF) is deposited on the electron transport layer to form a electron injecting layer by depositing 10 ⁇ thick.
  • an aluminum (Al) cathode is deposited to a thickness of 1,200 ⁇ on the electron injecting layer to form a cathode.
  • a light emitting device was manufactured.
  • the electroluminescence (EL) characteristics of the organic light emitting device manufactured as described above were measured by Maxiers M7000, and the reference luminance was 3,500 cd / m using the life measurement equipment (M6000) manufactured by McScience Inc. with the measurement result. When m 2 , T 95 was measured.
  • the driving voltage, the luminous efficiency, the external quantum efficiency, and the color coordinates (CIE) of the white organic light emitting diodes manufactured according to the present invention were measured.
  • the organic light emitting device using the charge generating layer material of the two-stack white organic light emitting device of the present invention has a lower driving voltage and improved luminous efficiency than Comparative Example 3.
  • the compound of the present invention used as an N-type charge generating layer composed of an invented backbone having appropriate length, strength and flat properties and a suitable heterocompound capable of binding to a metal is selected from alkali or alkaline earth metals. It is presumed that a gap state was formed in the N-type charge generation layer, and electrons generated from the P-type charge generation layer were easily injected into the electron transport layer through the gap state generated in the N-type charge generation layer. It seems to be. Therefore, the P-type charge generating layer can perform electron injection and electron transfer well to the N-type charge generating layer. Therefore, the driving voltage of the organic light emitting device is lowered, and the efficiency and lifetime are considered to be improved.
  • the transparent electrode ITO thin film obtained from the glass for OLED was subjected to ultrasonic cleaning for 5 minutes using trichloroethylene, acetone, ethanol and distilled water sequentially, and then stored in isopropanol and used.
  • N, N'-bis ( ⁇ -naphthyl) -N, N'-diphenyl-4,4'-diamine (N, N'-bis ( ⁇ -naphthyl) -N, N'-diphenyl-4,4'-diamine: NPB) was added thereto, and a 300 ⁇ thick hole transport layer was deposited on the hole injection layer by evaporation by applying a current to the cell.
  • a blue light emitting material having the following structure was deposited as a light emitting layer thereon. Specifically, H1, a blue light emitting host material, was vacuum deposited to a thickness of 200 ⁇ in one cell in the vacuum deposition equipment, and D1, a blue light emitting dopant material, was vacuum deposited on the cell at 5% of the host material.
  • Lithium fluoride (LiF) was deposited to an electron injecting layer with a thickness of 10 mW and an OLED was fabricated with an Al cathode having a thickness of 1000 mW.
  • the electroluminescence (EL) characteristics of the organic electroluminescent device manufactured as described above were measured with M7000's M7000, and the reference luminance was 700 cd through the life measurement equipment (M6000) manufactured by McScience Inc. with the measurement results. T 95 was measured at / m 2 .
  • the driving voltage, the luminous efficiency, the external quantum efficiency, and the color coordinate (CIE) of the organic light emitting device manufactured according to the present invention were measured as shown in Table 12.
  • the organic electroluminescent device using the electron transporting layer material of the blue organic light emitting device of the present invention has a lower driving voltage, and significantly improved luminous efficiency and lifetime compared to Comparative Example 4.
  • the compound of the present invention has improved in terms of driving, efficiency, and lifespan by improving the improved electron-transporting property or improved stability.

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Abstract

La présente invention concerne un composé hétérocyclique capable d'améliorer considérablement la durée de vie, l'efficacité, la stabilité électrochimique, et la stabilité thermique d'un élément électroluminescent organique; et un élément électroluminescent organique ayant une couche de composé organique contenant ledit composé hétérocyclique.
PCT/KR2016/004567 2015-04-29 2016-04-29 Composé hétérocyclique et dispositif électroluminescent organique utilisant ce composé WO2016175624A1 (fr)

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CN110016037A (zh) * 2019-03-08 2019-07-16 中山大学 一种新型氮杂稠环化合物及其制备方法和应用
CN110291088A (zh) * 2016-11-25 2019-09-27 喜星素材株式会社 杂环化合物以及使用此杂环化合物的有机发光装置
CN115232153A (zh) * 2021-04-23 2022-10-25 江苏三月科技股份有限公司 一种含有萘和1,10-菲啰啉结构的有机化合物及包含其的oled发光器件
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KR102414653B1 (ko) * 2017-09-29 2022-06-30 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR102110833B1 (ko) * 2018-12-06 2020-05-14 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
CN109608452B (zh) * 2018-12-24 2020-12-04 武汉天马微电子有限公司 有机化合物、显示面板及显示装置
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CN114656418B (zh) * 2022-04-10 2024-01-26 同济大学 一类(e)-苯并五元环-苯乙烯基硫鎓盐衍生物及其制备和应用

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CN109824576A (zh) * 2019-02-21 2019-05-31 青岛海洋生物医药研究院股份有限公司 一种有机光电材料中间体苯基茚并咔唑的合成方法
CN110016037A (zh) * 2019-03-08 2019-07-16 中山大学 一种新型氮杂稠环化合物及其制备方法和应用
CN110016037B (zh) * 2019-03-08 2021-10-22 中山大学 一种新型氮杂稠环化合物及其制备方法和应用
CN115232153A (zh) * 2021-04-23 2022-10-25 江苏三月科技股份有限公司 一种含有萘和1,10-菲啰啉结构的有机化合物及包含其的oled发光器件
US11878968B2 (en) 2021-07-09 2024-01-23 Plexium, Inc. Aryl compounds and pharmaceutical compositions that modulate IKZF2

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