WO2017018795A2 - Composé hétérocyclique et diode électroluminescente organique utilisant ce composé - Google Patents

Composé hétérocyclique et diode électroluminescente organique utilisant ce composé Download PDF

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WO2017018795A2
WO2017018795A2 PCT/KR2016/008189 KR2016008189W WO2017018795A2 WO 2017018795 A2 WO2017018795 A2 WO 2017018795A2 KR 2016008189 W KR2016008189 W KR 2016008189W WO 2017018795 A2 WO2017018795 A2 WO 2017018795A2
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substituted
unsubstituted
group
formula
compound
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PCT/KR2016/008189
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Korean (ko)
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WO2017018795A3 (fr
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박건유
오한국
이윤지
마재열
김동준
최진석
최대혁
이주동
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희성소재(주)
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Priority claimed from KR1020160057665A external-priority patent/KR101805686B1/ko
Application filed by 희성소재(주) filed Critical 희성소재(주)
Priority to US15/321,397 priority Critical patent/US10381577B2/en
Priority to EP16830828.6A priority patent/EP3330342B1/fr
Priority to CN201680048392.6A priority patent/CN107922837B/zh
Priority to JP2018504172A priority patent/JP6577133B2/ja
Publication of WO2017018795A2 publication Critical patent/WO2017018795A2/fr
Publication of WO2017018795A3 publication Critical patent/WO2017018795A3/fr

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    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond or a substituted or unsubstituted C 6 to C 60 arylene group,
  • Ar1 is a substituted or unsubstituted, C 2 Through C 60 Heteroaryl group containing at least one,
  • Ar2 is represented by any one of the following Chemical Formulas 3 and 4,
  • Y1 to Y4 are the same as or different from each other, and each independently a substituted or unsubstituted C 6 to C 60 aromatic hydrocarbon ring; Or substituted or unsubstituted C 2 to C 60 aromatic heterocycle,
  • 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 alkyl group; substituted or unsubstituted C 3 to C 60 cycloalkyl group A substituted or unsubstituted C 6 to C 60 aryl group, or a substituted or unsubstituted C 2 to C 60 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, and at least one of the organic material layers is a heterocyclic compound represented by Formula 1 above. It provides an organic light emitting device comprising a.
  • composition for an organic material layer of an organic light emitting device comprising a heterocyclic compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2 at the same time.
  • L 1 ′ is a C 6 to C 60 arylene group which is directly bonded or substituted or unsubstituted
  • Ar1 ' is a substituted or unsubstituted C 6 Through C 60 aryl group; Or a substituted or unsubstituted, C 2 Through C 60 A heteroaryl group containing at least one of S and O,
  • Ar2 ' is a substituted or unsubstituted C 6 Through C 60 Aryl group; Or a substituted or unsubstituted C 2 Through C 60 Heteroaryl group,
  • 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 alkyl group; substituted or unsubstituted C 3 to C 60 cycloalkyl group A substituted or unsubstituted C 6 to C 60 aryl group; or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
  • n ' is an integer of 0-2.
  • 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 for a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a charge generating layer, etc. 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 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.
  • heterocyclic compound represented by Formula 1 and the compound represented by Formula 2 may be used as a material of the light emitting layer of the organic light emitting device at the same time.
  • the driving voltage of the device is lowered, the light efficiency is improved, and the compound is thermally stabilized. Lifespan characteristics can be improved.
  • 1 to 3 are diagrams schematically showing a laminated structure of an organic light emitting device according to an exemplary embodiment of the present application.
  • FIG. 7 shows a graph of LTPL measurements at 339 nm wavelength of compound 1-11.
  • FIG. 13 shows a graph of LTPL measurements at 340 nm wavelength of Compound 1-27.
  • 16 shows a graph of LTPL measurements at 291 nm wavelength of Compound 1-33.
  • FIG. 17 shows a PL measurement graph of 239 nm wavelength of Compound 1-33.
  • FIG. 20 shows a PL measurement graph at 259 nm wavelength of Compound 1-39.
  • FIG. 23 shows a PL measurement graph at 260 nm wavelength of Compound 1-41.
  • FIG. 26 shows a PL measurement graph of 235 nm wavelength of Compound 1-65.
  • FIG. 31 is a graph of LTPL measurements at 361 nm wavelength of Compound 1-67.
  • FIG. 31 is a graph of LTPL measurements at 361 nm wavelength of Compound 1-67.
  • 35 shows a PL measurement graph of 308 nm wavelength of Compound 1-69.
  • FIG. 38 shows a PL measurement graph of 267 nm wavelength of Compound 1-70.
  • FIG. 41 is a graph of PL measurement at 241 nm wavelength of Compound 1-71.
  • FIG. 46 is a graph of LTPL measurements at 344 nm wavelength of Compound 1-82.
  • FIG. 47 shows a PL measurement graph at 307 nm wavelength of Compound 1-82.
  • FIG. 49 is a graph of LTPL measurements at 363 nm wavelength of Compound 1-84.
  • 50 shows a PL measurement graph at 298 nm wavelength of Compound 1-84.
  • FIG. 52 is a graph of LTPL measurements at 355 nm wavelength of Compound 1-99.
  • 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 3 may be represented by any one of the following structural formulas.
  • X 1 to X 6 in the structural formulas are the same as or different from each other, and each independently NR, S, O, or CR′R ′′,
  • 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 alkyl group; substituted or unsubstituted C 3 to C 60 cycloalkyl group A substituted or unsubstituted C 6 to C 60 aryl group; or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
  • n, o, p, q, r, and s are each independently the integer of 0-6.
  • Chemical Formula 4 may be represented by any one of the following structural formulas.
  • X7 and X8 in the above structural formula is the same as or different from each other, and each independently NR, S, O or CR'R ",
  • 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 alkyl group; substituted or unsubstituted C 3 to C 60 cycloalkyl group A substituted or unsubstituted C 6 to C 60 aryl group; or a substituted or unsubstituted C 2 to C 60 heteroaryl group,
  • t is an integer of 0-7.
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 5 to 10.
  • R1 to R6, R8, R9, R12, R13, R16, L1, Ar1, X1, X4, X5, m, n, q, r, and t are defined in Formula 1 and Structural Formula Is the same as the definition of
  • R1 to R6 of Formula 1 may be each independently hydrogen or deuterium.
  • R8 to R18 of the structural formulas are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted C 6 Through C 60 An aryl group; Or a substituted or unsubstituted C 2 Through C 60 It may be a heteroaryl group.
  • R, R 'and R “of the general formula (1) are the same as or different from each other, and each independently hydrogen; a substituted or unsubstituted C 1 to C 60 alkyl group; or a substituted or unsubstituted C 6 to C 60 aryl group.
  • composition for an organic material layer of the organic light emitting device is characterized in that it comprises a heterocyclic compound represented by the formula (1), and a compound represented by the formula (2) at the same time.
  • Chemical Formula 2 may be represented by any one of the following Chemical Formulas 11 to 22.
  • R1 'to R4' may be the same or different from each other.
  • R1 'to R4' of Chemical Formula 2 may be each independently hydrogen or deuterium.
  • Ar1 'of Chemical Formula 2 is a substituted or unsubstituted C 6 to C 60 aryl group; A substituted or unsubstituted, C 2 to C 60 heteroaryl group containing S; Or a substituted or unsubstituted, C 2 to C 60 heteroaryl group containing O.
  • Ar1 ′ of Formula 2 may be a phenyl group, a biphenyl group, a naphthyl group, an fluorene group substituted with an alkyl group, a dibenzothiophene group, or a dibenzofuran group.
  • Ar 2 ′ of Formula 2 may be a substituted or unsubstituted C 6 to C 60 aryl group.
  • Ar2 'of Formula 2 may be a phenyl group.
  • 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 alkyl group; substituted or unsubstituted C 3 to C 60 cyclo An alkyl group, a substituted or unsubstituted C 6 to C 60 aryl group, or a substituted or unsubstituted C 2 to C 60 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, deoxyyl 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.
  • Formula 1 may be represented by any one of the following compounds, but is not limited thereto.
  • Formula 2 may be represented by any one of the following 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 or 2 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.
  • composition for an organic material layer of an organic light emitting device comprising a heterocyclic compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2.
  • the weight ratio of the heterocyclic compound represented by Formula 1 in the composition: the compound represented by Formula 2 may be 1:10 to 10: 1, 1: 8 to 8: 1, and 1: 5 to 5 : 1, and 1: 2 to 2: 1, but is not limited thereto.
  • the composition may be used when forming the organic material of the organic light emitting device, and particularly preferably used when forming the host of the light emitting layer.
  • the composition may be a form in which two or more compounds are simply mixed, and may be mixed with a powder material before forming an organic material layer of the organic light emitting device, or may be mixed with a compound that is in a liquid state at an appropriate temperature or more.
  • the composition is in a solid state below the melting point of each material, and can be maintained in the liquid phase by adjusting the temperature.
  • 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 includes an anode, a cathode, and one or more organic material layers provided between the anode and the cathode, and at least one of the organic material layers is a hetero ring represented by Chemical Formula 1 It characterized in that it comprises a compound, and a compound represented by the formula (2).
  • An organic light emitting device is a conventional organic light emitting device, except that one or more organic material layers are formed using the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2. It can be produced by a method and a material for manufacturing a light emitting device.
  • the compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in manufacturing an 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.
  • the organic light emitting device includes an anode, a cathode and at least one organic layer provided between the anode and the cathode, one or more of the organic layer is a heterocyclic compound represented by the formula (1) And it includes a heterocyclic compound represented by the formula (2).
  • 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 a heterocyclic compound represented by Chemical Formula 1 above at least one layer of an organic material layer, or includes a heterocyclic compound represented by Chemical Formula 1 and a heterocyclic compound represented by Chemical Formula 2 at the same time. Except that it can be prepared by materials and methods known in the art.
  • 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.
  • organic compound layer containing the heterocyclic compound represented by Formula 1, and the heterocyclic compound represented by Formula 2 may further include other materials as necessary.
  • the heterocyclic compound represented by Formula 1, and the heterocyclic compound represented by Formula 2 may be used as a material of the charge generating layer in the organic light emitting device.
  • the heterocyclic compound represented by Chemical Formula 1 and the heterocyclic compound represented by Chemical Formula 2 may be used as an electron transport layer, a hole blocking layer, or a light emitting layer in an organic light emitting device.
  • the heterocyclic compound represented by Formula 1 and the heterocyclic compound represented by Formula 2 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.
  • heterocyclic compound represented by Formula 1, and the compound represented by Formula 2 may be used as a material of the light emitting layer in the organic light emitting device.
  • the heterocyclic compound represented by Formula 1, and the compound represented by Formula 2 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.
  • 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 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 / Camphor sulfonic acid or polyaniline / Poly (4-styrenesulfonate) (Polyaniline / Poly (4-styrene-sulfonate)) etc. can be used.
  • TCTA tri
  • 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. In this case, two or more light emitting materials may be deposited and used as separate sources, or premixed and deposited as one source.
  • 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 host of the same series may be mixed and used, or the host of another series may be mixed and used.
  • any two or more kinds of materials of n-type host material or P-type host material can be selected and used as the host material of the light emitting layer.
  • 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.
  • Table 21 shows NMR values
  • Tables 22 and 23 show measured values of a field desorption mass spectrometry (FD-MS).
  • FIG. 7 shows a graph of LTPL measurements at 339 nm wavelength of compound 1-11.
  • FIG. 13 shows a graph of LTPL measurements at 340 nm wavelength of Compound 1-27.
  • 16 shows a graph of LTPL measurements at 291 nm wavelength of Compound 1-33.
  • FIG. 17 shows a PL measurement graph of 239 nm wavelength of Compound 1-33.
  • FIG. 20 shows a PL measurement graph at 259 nm wavelength of Compound 1-39.
  • FIG. 23 shows a PL measurement graph at 260 nm wavelength of Compound 1-41.
  • FIG. 26 shows a PL measurement graph of 235 nm wavelength of Compound 1-65.
  • FIG. 31 is a graph of LTPL measurements at 361 nm wavelength of Compound 1-67.
  • FIG. 31 is a graph of LTPL measurements at 361 nm wavelength of Compound 1-67.
  • 35 shows a PL measurement graph of 308 nm wavelength of Compound 1-69.
  • FIG. 38 shows a PL measurement graph of 267 nm wavelength of Compound 1-70.
  • FIG. 41 is a graph of PL measurement at 241 nm wavelength of Compound 1-71.
  • FIG. 46 is a graph of LTPL measurements at 344 nm wavelength of Compound 1-82.
  • FIG. 47 shows a PL measurement graph at 307 nm wavelength of Compound 1-82.
  • FIG. 49 is a graph of LTPL measurements at 363 nm wavelength of Compound 1-84.
  • 50 shows a PL measurement graph at 298 nm wavelength of Compound 1-84.
  • FIG. 52 is a graph of LTPL measurements at 355 nm wavelength of Compound 1-99.
  • a glass substrate coated with a thin film of ITO to a thickness of 1,500 kPa was washed by distilled water ultrasonically. After washing the distilled water, ultrasonic washing with a solvent such as acetone, methanol, isopropyl alcohol and the like was dried and then UVO treated 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 an organic deposition thermal deposition apparatus.
  • PT plasma cleaner
  • the hole injection layer 2-TNATA (4,4 ', 4 "-Tris [2-naphthyl (phenyl) amino] triphenylamine) which is a common layer on the ITO transparent electrode (anode) and the hole transport layer NPB (N, N'-Di ( 1-naphthyl) -N, N'-diphenyl- (1,1'-biphenyl) -4,4'-diamine) was formed.
  • the light emitting layer was thermally vacuum deposited on it as follows.
  • the light emitting layer was deposited at 400 ⁇ with 7% doping of Ir (ppy) 3 to the host using Ir (ppy) 3 (tris (2-phenylpyridine) iridium) as a host, the compound shown in Table 24 below, as a green phosphorescent dopant.
  • 60 B of BCP was deposited as the hole blocking layer
  • 200 ⁇ of Alq 3 was deposited 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.
  • An electroluminescent device was manufactured.
  • the electroluminescent (EL) characteristics of the organic electroluminescent device manufactured as described above were measured by Maxiers M7000, and the reference luminance was 6,000 through the life equipment measuring equipment (M6000) manufactured by McScience Inc. with the measurement results. T 90 was measured at cd / m 2 .
  • the characteristics of the organic EL device of the present invention are shown in Table 24 below.
  • the organic electroluminescent device using the organic electroluminescent device light emitting layer material of the present invention has a lower driving voltage, improved luminous efficiency and a markedly improved lifetime as compared with Comparative Examples 1 to 7. .
  • a glass substrate coated with a thin film of ITO to a thickness of 1,500 kPa was washed by distilled water ultrasonically. After washing the distilled water, ultrasonic washing with a solvent such as acetone, methanol, isopropyl alcohol and the like was dried and then UVO treated 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 an organic deposition thermal deposition apparatus.
  • PT plasma cleaner
  • the hole injection layer 2-TNATA (4,4 ', 4 "-Tris [2-naphthyl (phenyl) amino] triphenylamine) which is a common layer on the ITO transparent electrode (anode) and the hole transport layer NPB (N, N'-Di ( 1-naphthyl) -N, N'-diphenyl- (1,1'-biphenyl) -4,4'-diamine) was formed.
  • the light emitting layer was thermally vacuum deposited on it as follows.
  • the light emitting layer was deposited with a compound of Formula 1 and a compound of Formula 2 at 400 kV from each individual source as a host and the green phosphorescent dopant was deposited by 7% doping of Ir (ppy) 3 .
  • 60 ⁇ of BCP was deposited as the hole blocking layer, and Alq 3 was deposited at 200 Hz.
  • 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.
  • An electroluminescent device was manufactured.
  • a glass substrate coated with a thin film of ITO to a thickness of 1,500 kPa was washed by distilled water ultrasonically. After washing the distilled water, ultrasonic washing with a solvent such as acetone, methanol, isopropyl alcohol and the like was dried and then UVO treated 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 an organic deposition thermal deposition apparatus.
  • PT plasma cleaner
  • the hole injection layer 2-TNATA (4,4 ', 4 "-Tris [2-naphthyl (phenyl) amino] triphenylamine) which is a common layer on the ITO transparent electrode (anode) and the hole transport layer NPB (N, N'-Di ( 1-naphthyl) -N, N'-diphenyl- (1,1'-biphenyl) -4,4'-diamine) was formed.
  • the light emitting layer was thermally vacuum deposited on it as follows.
  • the light emitting layer was pre-mixed with a compound of Formula 1 and a compound of Formula 2 as a host, and deposited 400 kPa in one park, and a green phosphorescent dopant was deposited by doping Ir (ppy) 3 with 7%.
  • 60 B of BCP was deposited as the hole blocking layer
  • 200 ⁇ of Alq 3 was deposited 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.
  • An electroluminescent device was manufactured.
  • the electroluminescent (EL) characteristics of the organic electroluminescent device manufactured as described above were measured by Maxiers M7000, and the reference luminance was 6,000 through the life equipment measuring equipment (M6000) manufactured by McScience Inc. with the measurement results. T 90 was measured at cd / m 2 .
  • Tables 25 to 27 Properties of the organic electroluminescent device of the present invention are as shown in Tables 25 to 27.
  • Table 25 is an example of simultaneously depositing two host compounds of Experimental Example 2 as a separate source
  • Table 26 is an example of depositing two light emitting layer compounds of Experimental Example 3 as a source after premixing
  • Table 27 In Experimental Example 2, a single host material is applied.
  • the organic light emitting device of the present invention includes a light emitting layer using a host and a phosphorescent dopant, and the host includes a host compound composed of a conventional single compound by being composed of a host compound (pn type) in which two or more compounds are mixed. There is an effect that has a lifespan characteristics superior to the organic light emitting device.
  • the pn type host of the present invention has the advantage of increasing the emission characteristics by adjusting the ratio of the host, which can be achieved by a suitable combination of P host with good hole mobility and n host with good electron mobility to be.
  • the light emitting host consisting of a plurality of compounds was pre-mixed with the compound, and then formed by depositing with one deposition source.
  • the uniformity and the thin film characteristics of the thin film may be improved, and the process may be simplified, the cost may be reduced, and the efficiency and the lifetime of the device may be improved.

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Abstract

La présente invention concerne un composé hétérocyclique apte à améliorer considérablement la durée de vie, l'efficacité, la stabilité électrochimique et la stabilité thermique d'une diode électroluminescente organique; et une diode électroluminescente organique dans laquelle le composé hétérocyclique est contenu dans une couche de composé organique.
PCT/KR2016/008189 2015-07-27 2016-07-27 Composé hétérocyclique et diode électroluminescente organique utilisant ce composé WO2017018795A2 (fr)

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US15/321,397 US10381577B2 (en) 2015-07-27 2016-07-27 Hetero-cyclic compound and organic light emitting device using the same
EP16830828.6A EP3330342B1 (fr) 2015-07-27 2016-07-27 Composé hétérocyclique et diode électroluminescente organique utilisant ce composé
CN201680048392.6A CN107922837B (zh) 2015-07-27 2016-07-27 杂环化合物和使用其的有机发光二极管
JP2018504172A JP6577133B2 (ja) 2015-07-27 2016-07-27 ヘテロ環化合物およびこれを用いた有機発光素子

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WO2018190516A1 (fr) * 2017-04-13 2018-10-18 주식회사 엘지화학 Nouveau composé hétérocyclique et élément électroluminescent organique utilisant celui-ci
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WO2020138814A1 (fr) * 2018-12-26 2020-07-02 엘티소재주식회사 Composé, diode optoélectronique organique et dispositif d'affichage
JP2021527625A (ja) * 2018-06-19 2021-10-14 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、これを含む有機発光素子、その製造方法および有機物層用組成物
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JP6128119B2 (ja) * 2012-05-09 2017-05-17 コニカミノルタ株式会社 有機エレクトロルミネッセンス素子、有機エレクトロルミネッセンス素子の製造方法、表示装置および照明装置
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WO2018190516A1 (fr) * 2017-04-13 2018-10-18 주식회사 엘지화학 Nouveau composé hétérocyclique et élément électroluminescent organique utilisant celui-ci
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JP2019108315A (ja) * 2017-12-20 2019-07-04 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． 有機エレクトロルミネッセンス素子用化合物、液状組成物、インク組成物、薄膜、及び有機エレクトロルミネッセンス素子
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