WO2018186670A1 - Composé et élément électroluminescent organique le comprenant - Google Patents

Composé et élément électroluminescent organique le comprenant Download PDF

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WO2018186670A1
WO2018186670A1 PCT/KR2018/003944 KR2018003944W WO2018186670A1 WO 2018186670 A1 WO2018186670 A1 WO 2018186670A1 KR 2018003944 W KR2018003944 W KR 2018003944W WO 2018186670 A1 WO2018186670 A1 WO 2018186670A1
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구기동
윤정민
김공겸
허난슬아
이기곤
금수정
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주식회사 엘지화학
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Priority to CN201880002724.6A priority Critical patent/CN109476682B/zh
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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
    • H10K85/658—Organoboranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • 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
    • H10K50/15—Hole transporting layers
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • 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
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other 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

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • W is a single bond, O or S,
  • X is B
  • Y is BRa
  • R1, R2, R3, R4, Ra, Rb and Z are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroring group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,
  • n is an integer from 0 to 8
  • n is an integer from 0 to 6
  • the compound described herein can be used as the material of the organic material layer of the organic light emitting device.
  • the compound according to at least one exemplary embodiment may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
  • the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron suppression, luminescence, hole suppression, electron transport, or electron injection material.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • the present specification provides a compound represented by the following Formula 1.
  • the compound represented by the following formula (1) is used in the organic material layer of the organic light emitting device, not only the efficiency of the organic light emitting device is always constant, but also has a low driving voltage and excellent life characteristics.
  • W is a single bond, O or S,
  • X is B
  • Y is BRa
  • R1, R2, R3, R4, Ra, Rb and Z are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroring group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,
  • n is an integer from 0 to 8
  • n is an integer from 0 to 6
  • the important heterocyclic center constituting the Formula 1 is typically 9.9-diphenylfluorene, 9,9-diphenyl-9H-xanthene, as shown in the following Formulas A-1 to A-6. , 9,9-diphenyl-9H-thioxanthene structure, all of which are known to be very rich in functional groups.
  • the hetero-rich ring composed of nitrogen or boron atoms is located adjacent to the heterocycle consisting of nitrogen or boron atoms which are relatively lacking in electrons such as the following functional groups such as Formulas A-1 to A-6. By donating the electrons, the stability of the compound having the structure of Formula 1 of the present application can be greatly improved.
  • Substituent definitions of Formulas A-1 to A-3 are the same as in Formula 2, and Substituent definitions of Formulas A-4 to A-6 are the same as in Formula 4.
  • the structure of the formula (1) is characterized in that the boron element is a solid ring formed of the central aryl amine, and the electrons of the boron aryl amine and spiro aryl amine has a stabilized form.
  • the emission spectrum is characterized by having a narrow half-value width
  • the color gamut of the device has a very large association with the half-width of the dopant material.
  • the half width when used as a fluorescent dopant, the half width reaches 20 nm to 40 nm, which is narrower than the half width of 40 nm or more, which is the half width of the material used as a conventional fluorescent dopant, and has a narrow half width.
  • spectral interference with a longer wavelength green spectrum may be less, thereby achieving a higher color reproducibility.
  • the HOMO energy level is higher in Compound 1 than in the case of [BD-2], which is a comparative compound, the electrons can be better received from the host molecule, and the generated excitons can be prevented from disappearing. have.
  • 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 replaced, that is, a position where the substituent can be substituted, if two or more are substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted is deuterium; Halogen group; Cyano group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted heteroarylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents.
  • 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 or may be interpreted as a substituent to which two phenyl groups are linked.
  • examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
  • the silyl group may be represented by the formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. Do not.
  • the boron group may be represented by a chemical formula of -BY d Y e , wherein Y d and Y e are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • the boron group may include, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, and phenylboron group.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4- Methyl-2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group , ter
  • the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, and the like.
  • the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C40. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, and the like, but is not limited thereto. .
  • Substituents comprising alkyl groups, alkoxy groups and other alkyl group moieties described herein include both straight and pulverized forms.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • the alkylamine group is not particularly limited in carbon number, but is preferably 1 to 40.
  • Specific examples of the alkylamine group include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, and the like, but are not limited thereto.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • arylamine group examples include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthra Cenylamine, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole and triphenyl amine group and the like, but are not limited thereto.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroaryl group in the heteroarylamine group may be a monocyclic hetero ring group or may be a polycyclic hetero ring group.
  • the heteroarylamine group including two or more heterocyclic groups may simultaneously include a monocyclic hetero ring group, a polycyclic hetero ring group, or a monocyclic hetero ring group and a polycyclic hetero ring group.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, peryllenyl group, triphenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • Spirofluorenyl groups such as (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenyl fluorenyl group).
  • the present invention is not limited thereto.
  • the heterocyclic group is a heterocyclic group containing one or more of N, O, P, S, Si, and Se as hetero atoms, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms.
  • heterocyclic group examples include, for example, pyridyl group, pyrrole group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, Triazole group, oxadiazole group, thiadiazole group, dithiazole group, tetrazole group, pyranyl group, thiopyranyl group, pyrazinyl group, oxazinyl group, thiazinyl group, deoxyyl group, triazinyl group, tetrazinyl group, qui Nolinyl group, isoquinolinyl group, quinolyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, acriridyl group, xanthenyl group
  • heteroaryl group is aromatic
  • adjacent The group may mean a substituent substituted with an atom directly connected to an atom in which the corresponding substituent is substituted, a substituent positioned closest in structural conformation to the substituent, or another substituent substituted in an atom in which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.
  • a “ring” means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted hetero ring.
  • the hydrocarbon ring may be an aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group except for the above-mentioned monovalent one.
  • the description of the aryl group may be applied except that the aromatic hydrocarbon ring is monovalent.
  • the heterocycle includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like.
  • the heterocycle may be monocyclic or polycyclic, may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the heteroaryl group except that it is not monovalent.
  • W is a single bond, O or S, and when W is a single bond, form a pentagonal ring.
  • Y is BRa
  • X is B
  • Y is O, S or NRb
  • X is N
  • X is B
  • Y is O, S, or NRb.
  • Y is BRa and X is N.
  • n is an integer of 0 to 8, and when n is 2 or more, R 1 is the same as or different from each other.
  • m is an integer of 0 to 2, when m is 2, R2 is the same as or different from each other.
  • the R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted tert-butyl group.
  • R1 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Or tert-butyl group.
  • R3, R4, Ra, Rb, and Z are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted alkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted heteroarylamine group; Or a substituted or unsubstituted heteroring group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.
  • R3, R4, Ra, Rb, and Z are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.
  • R3, R4, Ra, Rb, and Z are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.
  • R3, R4, Ra, Rb, and Z are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 12 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.
  • R3, R4, Ra, Rb, and Z are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 12 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or two or more of Z, R 3, R 4, and Ra combine with each other to form a substituted or unsubstituted ring.
  • R3, R4, Ra, Rb, and Z are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 12 carbon atoms; Or an aryl group having 6 to 20 carbon atoms unsubstituted or substituted with an alkyl group having 1 to 12 carbon atoms, or two or more of Z, R 3, R 4, and Ra combine with each other to form a substituted or unsubstituted ring.
  • R3, R4, Ra, Rb, and Z are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Substituted or unsubstituted propyl group; Substituted or unsubstituted t-butyl group; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.
  • R3, R4, Ra, Rb, and Z are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Substituted or unsubstituted propyl group; Substituted or unsubstituted t-butyl group; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group, or two or more of Z, R 3, R 4, and Ra combine with each other to form a substituted or unsubstituted ring.
  • R3, R4, Ra, Rb, and Z are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; Profile group; t-butyl group; A phenyl group unsubstituted or substituted with a methyl group, isopropyl group or tert-butyl group; Biphenyl group; Or a naphthyl group, or two or more of Z, R 3, R 4, and Ra combine with each other to form a substituted or unsubstituted ring.
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2 to 4.
  • Q1 and Q2 are the same as or different from each other, and each independently NR, O or S,
  • R and R11 to R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring.
  • Chemical Formula 2 may be represented by any one of the following Chemical Formulas 5 to 7.
  • R11 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine with R 3 to form a substituted or unsubstituted ring.
  • R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with R 3 to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • R11 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with R 3 to form a substituted or unsubstituted benzene ring.
  • R11 is hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group, or combines with R 3 to form a substituted or unsubstituted benzene ring.
  • R11 is hydrogen; heavy hydrogen; Methyl group; Ethyl group; Phenyl group; Or a naphthyl group, or combines with R 3 to form a substituted or unsubstituted benzene ring.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 8 to 12.
  • Q1 is NR, O or S
  • Q3 is a single bond, NR ', O or S,
  • R, R ', R31, R32, R35, R42 and R51 to R54 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkoxy group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, or adjacent substituents combine with each other to form a substituted or unsubstituted ring,
  • q1, q2 and q5 are each an integer of 0 to 3
  • s3 is an integer of 0 to 4,
  • s1 is an integer of 0 to 6
  • r is an integer of 0 to 7
  • s2 is an integer of 0 to 8
  • Q1 is NR, O or S.
  • Q2 is NR, O or S.
  • Q3 is a single bond, NR ', O or S.
  • R and R ' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or adjacent substituents combine to form a substituted or unsubstituted ring.
  • R and R ' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with adjacent substituents to form a substituted or unsubstituted ring.
  • R and R ' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; Phenyl group; Or a naphthyl group, or adjacent substituents combine to form a substituted or unsubstituted ring.
  • R31, R32, R35, R42, R51 to R54 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, or adjacent substituents combine to form a substituted or unsubstituted ring.
  • R31, R32, R35, R42, R51 to R54 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms; Substituted or unsubstituted arylamine group having 6 to 60 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroring group, or adjacent substituents combine to form a substituted or unsubstituted ring.
  • R31, R32, R35, R42, R51 to R54 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; Isopropyl group; tert-butyl group; Methoxy group; Diphenylamine group; diphenylamine group substituted with tert-butyl group; Phenyl group; Carbazole groups; Biphenyl group; A phenyl group substituted with a carbazole group; It is a carbazole group substituted with a morpholine group or deuterium.
  • R12 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine with R4 to form a substituted or unsubstituted ring.
  • R12 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with R4 to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • R12 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with R4 to form a substituted or unsubstituted benzene ring.
  • R12 is the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; Phenyl group; Or a naphthyl group, or combines with R 4 to form a substituted or unsubstituted benzene ring.
  • R13 and R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine to form a substituted or unsubstituted ring.
  • R13 and R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • R13 and R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine to form a substituted or unsubstituted benzene ring.
  • R13 and R14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl group; Ethyl group; Phenyl group; Or a naphthyl group, or combine to form a substituted or unsubstituted benzene ring.
  • Q2 is NR, O or S.
  • Q2 is NR.
  • Q2 is NR and R is hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or combine with an adjacent substituent to form a ring.
  • Q2 is NR and R is hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or combine with an adjacent substituent to form a ring.
  • Q2 is NR, and R is hydrogen; Substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Substituted or unsubstituted t-butyl group; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted naphthyl group, or combine with an adjacent substituent to form a ring.
  • Q2 is NR, and R is hydrogen; Substituted or unsubstituted methyl group; Ethyl group; t-butyl group; Phenyl group; Biphenyl group; Or a naphthyl group, or combine with an adjacent substituent to form a ring.
  • q1 is 0 to 2
  • R31 is the same as or different from each other.
  • R32 is the same as or different from each other.
  • R35 is the same as or different from each other.
  • R52 is the same as or different from each other.
  • R51 is the same as or different from each other.
  • R53 is the same as or different from each other.
  • R53 is the same as or different from each other.
  • Chemical Formula 1 may be represented by any one of the following chemical structures.
  • Compound of Formula 1 according to an exemplary embodiment of the present specification can be prepared in the core structure as shown in the following scheme. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
  • [Intermediate 1-b] was synthesized by introducing a ketal form substituent into phenones of [Intermediate 1-a] using ethylene glycol.
  • a cyclic intermediate [intermediate 1-c] can be synthesized through a coupling reaction.
  • a compound corresponding to Chemical Formula 1 may be synthesized using a synthesis method similar to that of synthesizing the final product.
  • the conjugation length of the compound and the energy bandgap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.
  • a compound having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above.
  • the HOMO and LUMO energy levels of the compound may be controlled by introducing various substituents into the core structure of the above structure.
  • the compound which has the intrinsic property of the introduced substituent can be synthesize
  • a substituent mainly used in the hole injection layer material, the hole transport material, the light emitting layer material, and the electron transport layer material used in the manufacture of the organic light emitting device into the core structure, it is possible to synthesize a material satisfying the requirements of each organic material layer. Can be.
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.
  • the organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is formed using the above-described compound.
  • the compound may be formed as an organic material 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 material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic material layers.
  • the organic material layer may include an electron transport layer or an electron injection layer, the electron transport layer or an electron injection layer may include a compound represented by the formula (1).
  • the organic material layer may include a hole injection layer or a hole transport layer
  • the hole injection layer or hole transport layer may include a compound represented by the formula (1).
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the compound represented by Formula 1 may be included as a dopant of the light emitting layer.
  • the organic material layer including the compound represented by Chemical Formula 1 may include the compound represented by Chemical Formula 1 as a dopant, and may include a fluorescent host or a phosphorescent host.
  • the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals, or metal compounds. May be included as the dopant.
  • the organic material layer including the compound represented by Chemical Formula 1 may include the compound represented by Chemical Formula 1 as a dopant, include a fluorescent host or a phosphorescent host, and may be used with an iridium-based (Ir) dopant. have.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
  • the compound may be included in the light emitting layer (3).
  • FIG. 2 illustrates an organic light emitting device in which an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8, and a cathode 4 are sequentially stacked on a substrate 1.
  • the structure is illustrated.
  • the compound may be included in the hole injection layer 5, the hole transport layer 6, the light emitting layer 7, or the electron transport layer 8.
  • the organic light emitting device uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate. It can be prepared by depositing an anode to form an anode, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • PVD metal vapor deposition
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure.
  • the organic layer may be prepared by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention 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-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • 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.
  • the hole injection material is a material capable of well injecting holes from the anode at a low voltage, and the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic material layer.
  • hole injecting materials include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transporting material a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
  • a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
  • Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the emission layer may emit red, green, or blue light, and may be formed of a phosphor or a fluorescent material.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • Alq 3 8-hydroxyquinoline aluminum complex
  • Carbazole series compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Benzoxazole, benzthiazole and benzimidazole series compounds include Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Iridium complex used as the dopant of the light emitting layer is as follows, but is not limited thereto.
  • the electron transporting material is a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer.
  • a material having high mobility to electrons is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer.
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the glass substrate coated with ITO indium tin oxide having a thickness of 1300 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the following compound [HI-A] was vacuum deposited to a thickness of 600 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • the following compound [HAT-CN] (50 kPa) and the following compound [HT-B] (600 kPa) were sequentially vacuum deposited on the hole injection layer to form a hole transport layer.
  • the present invention provides a light emitting layer on the hole transport layer.
  • [Compound 1] was doped at 2.5 wt% relative to [BH-A] and vacuum deposited to a film thickness of 200 kPa.
  • the organic light emitting device was manufactured by maintaining 7 to 5 ⁇ 10 -8 torr.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 3 instead of Compound 1.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 5 instead of Compound 1.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 11 instead of Compound 1.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 15 instead of Compound 1.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 17 instead of Compound 1.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using Compound 28 instead of Compound 1.
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using [BH-B] instead of [BH-A].
  • Example 1 an organic light emitting diode was manufactured according to the same method as Example 1 except for using [BH-C] instead of [BH-A].
  • Example 2 an organic light emitting diode was manufactured according to the same method as Example 2 except for using [BH-B] instead of [BH-A].
  • Example 2 an organic light emitting diode was manufactured according to the same method as Example 2 except for using [BH-C] instead of [BH-A].
  • Example 4 an organic light emitting diode was manufactured according to the same method as Example 4 except for using [BH-B] instead of [BH-A].
  • Example 4 an organic light emitting diode was manufactured according to the same method as Example 4 except for using [BH-C] instead of [BH-A].
  • Example 5 an organic light emitting diode was manufactured according to the same method as Example 5 except for using [BH-B] instead of [BH-A].
  • Example 5 an organic light emitting diode was manufactured according to the same method as Example 5 except for using [BH-C] instead of [BH-A].
  • Example 6 an organic light emitting diode was manufactured according to the same method as Example 6 except for using [BH-B] instead of [BH-A].
  • Example 6 an organic light emitting diode was manufactured according to the same method as Example 6 except for using [BH-C] instead of [BH-A].
  • Example 7 an organic light emitting device was manufactured in the same manner as in Example 7, except that [BH-B] was used instead of [BH-A].
  • Example 7 an organic light emitting device was manufactured in the same manner as in Example 7, except that [BH-C] was used instead of [BH-A].
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that [BD-A] was used instead of Compound 1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that [BD-B] was used instead of Compound 1 in Example 1.
  • Comparative Example 1 an organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using [BH-B] instead of [BH-A].
  • Comparative Example 2 an organic light emitting diode was manufactured according to the same method as Comparative Example 2 except for using [BH-B] instead of [BH-A].
  • Comparative Example 1 an organic light emitting diode was manufactured according to the same method as Comparative Example 1 except for using [BH-C] instead of [BH-A].
  • Comparative Example 2 an organic light emitting diode was manufactured according to the same method as Comparative Example 2 except for using [BH-C] instead of [BH-A].
  • the driving voltage and the luminous efficiency of the organic light emitting device were measured at a current density of 10 mA / cm 2 , and a time (T 95 ) of 95% of the initial luminance at a current density of 20 mA / cm 2 was measured. .
  • T 95 a time of 95% of the initial luminance at a current density of 20 mA / cm 2 was measured.
  • Table 1 The results are shown in Table 1 below.
  • the compound represented by Formula 1 according to the present invention can be used as a fluorescent dopant in an organic light emitting device.
  • the organic light emitting device using the same shows high efficiency and long life.
  • Examples 8 to 19 show the results of the combination experiments with the hosts of different characteristics, and showed excellent fluorescence characteristics even in the experiments with the different types of hosts.

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Abstract

La présente invention concerne un composé représenté par la formule chimique 1 et un élément électroluminescent organique le comprenant.
PCT/KR2018/003944 2017-04-03 2018-04-03 Composé et élément électroluminescent organique le comprenant WO2018186670A1 (fr)

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